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Title:
Substituted pyridine herbicides
Kind Code:
A1


Abstract:
1embedded image

Compounds of formula (I), in which the substituents are as defined in claim 1 and the agrochemically tolerated salts M+ and all stereoisomers and tautomers of the compounds of formula (I) are suitable for use as herbicides.




Inventors:
Edmunds, Andrew (Basel, CH)
Luthy, Christoph (Munchenstein, CH)
Seckinger, Karl (Riegel, DE)
Mesmaeker, Alain De (Kaenerkinden, CH)
Kunz, Walter (Oberwil, CH)
Schaetzer, Jurgen (Rheinfelden, DE)
Application Number:
09/887372
Publication Date:
02/27/2003
Filing Date:
06/22/2001
Export Citation:
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Assignee:
EDMUNDS ANDREW
LUTHY CHRISTOPH
SECKINGER KARL
MESMAEKER ALAIN DE
KUNZ WALTER
SCHAETZER JURGEN
Primary Class:
504/251
Other Classes:
504/255, 504/260, 546/268.1, 546/281.7, 546/286, 546/298, 546/315
International Classes:
A01N43/40; C07D213/50; C07D213/643; C07D213/70; C07D213/71; C07D213/74; C07D213/76; C07D213/80; C07D213/84; C07D213/89; C07D401/06; C07D401/12; C07D401/14; C07D405/06; C07D405/08; C07D409/06; C07D213/64; (IPC1-7): C0745/02; A01N43/40; C07D213/46; C0741/02
View Patent Images:
Download PDF 20030040437  
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Primary Examiner:
NORTHINGTON DAVI, ZINNA
Attorney, Agent or Firm:
William A. Teoli, Jr. (Greensboro, NC, US)
Claims:

What is claimed is:



1. A compound of the formula I 177embedded image in which p is 0 or 1; R5 is C1-C6haloalkyl; R2 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, vinyl which is substituted by C1-C2alkoxycarbonyl or phenyl, or is C2-C6alkynyl, C2-C6haloalkynyl, ethynyl which is substituted by trimethylsilyl, hydroxyl, C1-C2alkoxy, C1-C2alkoxycarbonyl or phenyl, or is C3-C6allenyl, C3-C6cycloalkyl, C3-C6cycloalkyl which is substituted by halogen, or is C1-C6alkoxy, C3-C6alkenyloxy, C3-C6-alkynyloxy, CG-C6haloalkoxy, C3-C6haloalkenyloxy, cyano-C1-C4alkoxy, C1-C4alkoxy-C1-C4alkoxy, C1-C4alkylthio-C1-C4alkoxy, C1-C4alkylsulfinyl-C1-C4alkoxy, C1-C4alkylsulfonyl-C1-C4alkoxy, C1-C4alkoxycarbonyl-C1-C4alkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C4alkoxycarbonyl-C1-C4alkylthio, C1-C4-alkoxycarbonyl-C1-C4alkylsulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, benzyl-S(O)n1—, C1-C6alkylamino, C2-C6dialkylamino, C1-C6alkylaminosulfonyl, di-(C1-C6alkylamino)sulfonyl, benzyloxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl-containing groups, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro or R2 is OS(O)n2-R21, N(R23)-S(O)n3-R22, cyano, carbamoyl, C1-C4alkoxycarbonyl, formyl, halogen, thiocyanato, amino, hydroxy-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-S(O)n4-C1-C4alkyl, cyano-C1-C4alkyl, C1-C6alkylcarbonyloxy-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4alkoxycarbonyloxy-C1-C4alkyl, C1-C4thiocyanato-C1-C4alkyl, benzoyloxy-C1-C4alkyl, C2-C6oxiranyl, C1-C4alkylamino-C1-C4alkyl, di-(C1-C4-alkyl)amino-C1-C4alkyl, C1-C12alkylthiocarbonyl-C1-C4alkyl or formyl-C1-C4alkyl, or R2 is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4alkylene, —CH═CH—, —COC—, —CH2O—, —CH2N(C1-C4alkyl)—, —CH2SO—, or —CH2SO2 group and it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C6acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C3haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-Chaloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; R3 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C6alkylamino, C2-C6dialkylamino, C1-C6alkylaminosultonyl, C2-C6dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or R3 is —N(R23)—S(O)n—R22, cyano, halogen, amino, C1-C4alkoxy-C1-C4alkyl or C1-C4alkyl-S(O)n-C1-C4alkyl; R4 is hydrogen, C1-C6alkyl, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6haloalkenyloxy, C3-C6alkynyloxy, C1-C4alkylcarbonyloxy, C1-C4alkylsulfonyloxy, tosyloxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C1-C4dialkylamino, C1-C4alkoxycarbonyl, C1-C4haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; or R4 is a five to ten-membered monocyclic or R3-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system, unless fused, being bonded to the pyridine ring directly or via a C1-C4alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)—, —CH2S—, —CH2SO—, or —CH2SO2— group and it not being possible for the ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, CG-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C4alkoxy-C1-C2alkylthio, C1-C4alkylcarbonyl-C1-C2alkylthio, C1-C4alkoxycarbonyl-C1-C2alkylthio, cyano-C1-C4alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; R21 is C1-C4alkyl or C1-C4haloalkyl; R22 is C1-C4alkyl, C1-C4haloalkyl or di-(C1-C4alkyl)amino; R23, R24, R25 independently of one another are hydrogen or C1-C4alkyl; n, n1, n2, n3 and n4 independently of one another are 0, 1 or 2; Q is Q1 178embedded image in which R6, R7, R8 and R9 independently of one another are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkyl-S(O)n17, C1-C6alkyl-NHS(O)2, C1-C6alkylamino, di-(C1-C6alkyl)amino, hydroxyl, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, hydroxy-C1-C6alkyl, C1-C4alkylsulfonyloxy-C1-C6alkyl, tosyloxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkyl-S(O)n4-C1-C6alkyl, cyano-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy, benzyloxy-C1-C6alkyl, C1-C6alkoxycarbonyl-C1-C6alkyl, C1-C6alkoxycarbonyloxy-C1-C6alkyl, thiocyanato-C1-C6alkyl, oxiranyl, C1-C6alkylamino-C1-C6alkyl, di(C1-C6alkyl)amino-C1-C6alkyl, formyl-C1-C6alkyl, C1-C6alkyloximo, halogen, cyano, nitro, phenyl or phenyl which is substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n18, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n5, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)n19N(C1-C4alkyl)2, halogen, nitro, COOH or cyano; or adjacent R6 and R7 or R8 and R9 together are -(CH2)m—, C(O)O(CH2)n20— or —S(O)n21 (CH2)n22—; n5, n17, n18, n19 and n21 independently of one another are 0, 1 or 2; n20 is 2 or 3; n22 is 2, 3 or 4; m is2, 3, 4, 5, or 6; W is oxygen, S(O)n6—CR11R12, —CR63R64CR65R66, —C(O)— or —NR13; R63, R64, R65 and R66 independently of one another are hydrogen or C1-C6alkyl, or R65 together with R7 or R9 forms a direct bond; n6 is 0, 1 or 2; R1, is hydrogen, C1-C4alkyl, C1-C4haioalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylthio-C3-C6cycloalkyl, C1-C4alkycarbonyloxy-C1-C4alkyl, C1-C4alkysulfonyloxy-C1-C4alkyl, tosyloxy-C1-C4alkyl, di-(C1-C3alkoxyalkyl)methyl, di-(C1-C3alkthioalkyl)methyl, (C1-C3alkoxyalkyl)-(C1-C3alkthioalkyl)methyl, C3-C5oxacycloalkyl, C3-C5thiacycloalkyl, C3-C4dioxacycloalkyl, C3-C4dithiacycloalkyl, C3-C4oxathiacycloalkyl, formyl, C1-C4alkoxycarbonyl, carbamoyl, C1-C4alkylaminocarbonyl, di-(C1-C4alkyl)aminocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl or phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n21, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n7, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)n20N(C1-C4alkyl), halogen, nitro, COOH or cyano; n7, n20 and n21 independently of one another are 0, 1 or 2; or R12 together with R6 or R9 is a group —(CH2)o—; o is 1, 2, 3, 4 or 5; R12 is hydrogen, C1-C4alkyl or C1-C4haloalkyl; or R12 together with R1, is a group —(CH2)m1; m1 is 2, 3, 4, 5, or 6; R10 is hydroxyl, O−M+, halogen, cyano, SCN, OCN, C1-C12alkoxy, C1-C4alkoxycarbonyl-C1-C4alkoxy, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylthio, C1-C12haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C6alkoxy-C1-C6alkylthio, C1-C6alkoxy-C1-C6alkylsulfinyl, C1-C6alkoxy-C1-C6alkylsulfonyl, C2-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12haloalkenylsulfonyl, C1-C4-alkoxycarbonyl-C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkylsulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, (C1-C4alkoxy)2P(O)O, C1-C4alkyl-(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, R14R15N, R14R15NNH, R16R17NC(O)O—, R16R17NC(O)NH—, C1-C12alkyl-S(O)2NR18, C1-C4haloalkyl-S(O)2NRP9, C1-C12alkyl-S(O)2O, C1-C4haloalkyl-S(O)2O, C1-C18alkylcarbonyloxy, it being possible for the alkyl group to be substituted by halogen, C1-C6alkoxy, C1-C6alkylthio or cyano, or is C2-C18alkenylcarbonyloxy, C2-C18alkynylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylthiocarbonyloxy, C1-C12alkylthiocarbamoyl, C1-C6alkyl-NH(CS)N(C1-C6alkyl)-NH—, di-C1-C6alkyl-N(CS)N(C1-Cralkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano; or R10 is a group Ar1-thio, Ar2-sulfinyl, Ar3-sulfonyl, —OCO—Ar4 or NH—Ar5 in which Ar1, Ar2, Ar3, Ar4 and Ar5 independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, and it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic rings are other than halogen; R14, R15, R16, R17 and R18 independently of one another are hydrogen or C1-C6alkyl; n8, n9, n10, n11, n12, n13 and n14 independently of one another are 0, 1 or 2; R13 is hydrogen, C1-CO4alkyl, C1-C4alkythio-C1-C4carbonyl, C1-C4alkylsulfinyl-C1-C4carbonyl, C1-C4alkylsulfonyl-C1-C4carbonyl, C1-C4-alkoxycarbonyl, C1-C4alkylcarbonyl, phenylcarbonyl, or is phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4-alkylamino, C1-C4alkyl-S(O)n15, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n16, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro, or cyano; and n15 and n16 independently of one another are 0, 1 or 2; or an agrochemically tolerated salt M+or a stereoisomer or tautomer of a compound of the formula I.

2. A compound according to claim 1, wherein p is 0; R5 is C1-C6haloalkyl; R2 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6-alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, benzyl-S(O)n1—, C1-C6alkylamino, C2-C6dialkylamino, C1-C6-alkylaminosulfonyl, C2-C6-dialkylaminosulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl group, in turn, to be substituted by C1-C3-alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or is OS(O)n2-R21, N(R23)-S(O)n3-R22, cyano, halogen, amino, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-S(O)n4-C1-C4alkyl, cyano-C1-C4alkyl or C1-C4alkoxy-C1-C4alkoxy; R3 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-Crcycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6-alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-Cfalkylamino, C2-C6dialkylamino, C1-C6-alkylaminosulfonyl, C2-C6-dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or is —N(R23)—S(O)n—R22, cyano, halogen, amino, C1-C4alkoxy-C1-C4alkyl or C1-C4alkyl-S(O)n—C1-C4alkyl; R4 is hydrogen, C1-C6alkyl, C1-C4alkoxy, CG-C4haloalkoxy, C1-C4alkylcarbonyloxy, C1-C4-Alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsuifonyl, C1-C4haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; or R4 is a five- to ten-membered monocyclic or R3-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4alkylene group and it not being possible for the ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6-Alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C4-alkoxy-C1-C2alkylthio, C1-C4alkylcarbonyl-C1-C2alkylthio, C1-C4alkoxycarbonyl-C1-C2alkylthio, cyano-C1-C4alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulionyl, aminosulfonyl, C1-C2alkylaminosulfonyl, C2-C4dialkylaminosuffonyl, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; R21 and R22 independently of one another are C1-C4alkyl or C1-C4haloalkyl; R23 R24 and R25 independently of one another are hydrogen or C1-C4alkyl; n, n1, n2, n3 and n4 independently of one another are 0, 1 or 2; Q is Q1 179embedded image in which R6, R7, R8 and R9 independently of one another are hydrogen, C1-C6alkyl, C1-C6-haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxycarbonyl, C1-C6alkyl-S(O)n17, C1-C6alkyl-NHS(O)2, C1-C6alkylamino, di-(C1-C6alkyl)amino, hydroxyl, C1-C6alkoxy, C3C6alkenyloxy, C3-C6-alkynyloxy, hydroxy-C1-C6alkyl, C1-C4alkylsulfonyloxy-C1-C6alkyl, tosyloxy-C1-C6alkyl, halogen, cyano, nitro, phenyl or phenyl which is substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4-alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n18, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n5, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)n19N(C1-C4alkyl), halogen, nitro, COOH or cyano; or adjacent R6 and R7 or R8 and R9 together are -(CH2)m—; n5 n17, n18 and n19 independently of one another are 0, 1 or 2; m is 2, 3, 4, 5, or 6; W is oxygen, S(O)n6, —CR11,R12—, —C(O)— or —NR13—; n6 is 0, 1 or 2; R11 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylcarbonyloxy-C1-C4alkyl, C1-C4alkylsulfonyloxy-C1-C4alkyl, tosyloxy-C1-C4alkyl, di-(C1-C3alkoxyalkyl)methyl, di-(C1-C3alkylthioalkyl)methyl, (C1-C3alkoxyalkyl)-(C1-C3alkylthioalkyl)methyl, C3-C5oxacycloalkyl, C3-Csthiacycloalkyl, C3-C4dioxacycloalkyl, C3-C4-dithiacycloalkyl, C3-C4oxathiacycloalkyl, formyl, C1-C4alkoxycarbonyl or phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4-alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n21, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n7, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O),2oN(C1-C4alkyl), halogen, nitro, COOH or cyano; n7, n20 and n21 independently of one another are 0, 1 or 2; or R12 together with R9 is a group —(CH2)o—; o is 1, 2, 3, 4 or 5; R12 is hydrogen, C1-C4alkyl or C1-C4haloalkyl; or R12 together with R1 is a group —(CH2)m1; m1 is 2, 3, 4, 5, or 6; R10 is hydroxyl, O−M+, halogen, C1-C12alkoxy, C1-C12alkylcarbonyloxy, C2-C4-alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C2-C12-alkylcarbonyloxy, R23R24N-C(O)O, C1-C12alkylS(O)n8—, C1-C4haloalkyl-S(O)n9—, C2-C12-alkenylS(O)nlo-, C2-C12haloalkenylS(O)n11-, C2-C12alkynylS(O)n12-; benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl group, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n13, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n14, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano, or is C1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4-alkoxy)2P(O)O, C1-C4alkyl(C1-C4alkoxy)P(O)O, or H(C1-C4alkoxy)P(O)O; n8, n9, n10, n11, n12, n13 and n14 independently of one another are 0, 1 or 2; R13 is hydrogen, C1-C4alkyl, C1-C4alkoxycarbonyl or phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n15, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)nl6, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano; n15 and n16 independently of one another are 0, 1 or 2; or an agrochemically tolerated salt M+ or a stereoisomer or tautomer of a compound of the formula I.

3. A compound according to claim 1, in which R10 is hydroxyl or O−M+.

4. A compound according to claim 1, in which W is oxygen, —CR11R12— or —C(O)—.

5. A compound according to claim 1, in which W is oxygen and R6, R7, R8 and R9 independently of one another are hydrogen or C1-C3alkyl.

6. A compound according to claim 1, in which W is —C(O)— and R6, R7, R8 and R9 independently of one another are C1-C3alkyl.

7. A compound according to claim 1, in which R2 is hydrogen and R3 is methyl.

8. A compound according to claim 1, in which R2 is methyl, ethyl, n-propyl, i-propyl, vinyl, methoxymethyl, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, acetoxymethyl, propionyloxymethyl, chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl or cyanomethyl.

9. A compound according to claim 1, in which R4 is hydrogen or methyl.

10. A compound according to claim 1, in which R5 is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoropropyl or difluoromethyl.

11. A compound according to claim 1, in which R3 is hydrogen and R2 is C1-C4alkyl, C1-C3haloalkyl, cyclopropyl, C2-C3alkenyl, C2-C3haloalkenyl, C2-C3alkynyl, allenyl, C1-C2-alkoxy-C1-C2alkyl, C1-C2alkylthio-C1-C2alkyl, cyano-C1-C2alkyl, C1-C2alkoxycarbonyl-C1-C2-alkyl, C1-C4alkylcarbonyloxy-C1-C2alkyl, C1-C3alkoxy, C1-C3haloalkoxy, allyloxy, propargyloxy, C1-C3alkylthio, C1-C3alkylsulfinyl or cyano.

12. A compound of the formula IIIa 180embedded image in which R501 is C1-C6haloalkyl; R301 is hydrogen; R401 is hydrogen or C1-C6alkyl; and R201 is C1-C5alkyl, C1-C6haloalkyl-C1-C4alkyl, C2-C6alkenyl, C2-C6haloalkenyl, or C1-C2-alkoxycarbonyl- or phenyl-substituted vinyl, C2-C6alkynyl or C2-C6haloalkynyl; or trimethylsilyl-, hydroxyl-, C1-C2alkoxy-, C1-C2alkoxycarbonyl- or phenyl-substituted ethynyl or C3-C6allenyl; or C3-C6cycloalkyl, halogen-substituted C3-C6cycloalkyl, C1-C4alkoxy-C1-C4-alkyl, C1-C4alkyl-S(O),4-C1-C4alkyl, cyano-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4-thiocyanato, oxiranyl, C1-C4alkylamino-C1-C4alkyl, C1-C4dialkylamino-C1-C4alkyl, hydroxy-C1-C4alkyl, C1-C12alkylthiocarbonyl-C1-C4alkyl or formyl-C1-C4alkyl, or R20, is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4-alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)-, —CH2S—, —CH2SO— or —CH2SO2-group and it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloaikynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6-alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are other than halogen; and X is halogen or cyano.

13. A compound of the formula XVIa 181embedded image in which R501 is C1-C6haloalkyl; R301 is hydrogen; R401 is hydrogen or C1-C6alkyl; and R201 is C1-C6alkyl, C1-C6haloalkyl-C1-C4alkyl, C2-C6alkenyl, C2-C6haloalkenyl, or C1-C2-alkoxycarbonyl- or phenyl-substituted vinyl, C2-C6alkynyl or C2-C6haloalkynyl; or irimethylsilyl-, hydroxyl-, C1-C2alkoxy-, C1-C2alkoxycarbonyl- or phenyl-substituted ethynyl or C3-C6allenyl; or C3-C6cycloalkyl, halogen-substituted C3-C6cycloalkyl, C1-C4alkoxy-C1-C4-alkyl, C1-C4alkyl-S(O)n4-C1-C4alkyl, cyano-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4-thiocyanato, oxiranyl, C1-C4alkylamino-C1-C4alkyl, C1-C4dialkylamino-C1-C4alkyl, hydroxy-C1-C4alkyl, C1-C12alkylthiocarbonyl-C1-C4alkyl or formyl-C1-C4alkyl, or R201 is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4-alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)—, —CH2S—, —CH2SO— or —CH2SO2-group and it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C37 C6haloalkenylthio, C3-C6-alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are other than halogen; and X is halogen or cyano, with the proviso that, when R501 is trifluoromethyl and, simultaneously, R301 and R401 are hydrogen, then R201 is other than C1-C6alkyl.

14. Herbicidal and plant-growth-inhibitory composition, which has a herbicidally active content of a compound of the formula I on an inert carrier.

15. A method of controlling undesired vegetation, in which a herbicidally active amount of an active ingredient of the formula I or of a composition comprising this active ingredient is applied to the plants or their environment.

16. A method of inhibiting plant growth, in which a herbicidally active amount of an active ingredient of the formula I or of a composition comprising this active ingredient is applied to the plants or their environment.

17. The use of a composition according to claim 14 for controlling undesired plant growth.

Description:
[0001] The present invention relates to novel, herbicidally active pyridine ketones, to their preparation, to compositions comprising these compounds, and to their use for controlling weeds, especially in crops of useful plants, or for inhibiting plant growth.

[0002] Herbicidally active pyridine ketones are described, for example, in WO 97/46530. There have now been found novel pyridine ketones which have herbicidal and growth-inhibitory properties.

[0003] The present invention therefore relates to compounds of the formula I 2embedded image

[0004] in which

[0005] p is 0 or 1;

[0006] R5 is C1-C6haloalkyl;

[0007] R2 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, vinyl which is substituted by C1-C2alkoxycarbonyl or phenyl, or is C2-C6alkynyl, C2-C6haloalkynyl, ethynyl which is substituted by trimethylsilyl, hydroxyl, C1-C2alkoxy, C1-C2alkoxycarbonyl or phenyl, or is C3-C6alkenyl, C3-C6cycloalkyl, C3-C6cycloalkyl which is substituted by halogen, or is C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6haloalkoxy, C3-C6haloalkenyloxy, cyano-C1-C4alkoxy, C1-C4alkoxy-C1-C4alkoxy, C1-C4alkylthio-C1-C4alkoxy, C1-C4alkylsulfinyl-C1-C4alkoxy, C1-C4alkylsulfonyl-C1-C4alkoxy, C1-C4alkoxycarbonyl-C1-C4alkoxy, C1-6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsufonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C4alkoxycarbonyl-C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkylsulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, benzy[-S(O)n1-, C1-C6alkylamino, C2-C6dialkylamino, C1-C6alkylaminosulfonyl, di-(C1-C6alkytamino)sulfonyl, benzyloxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl-containing groups, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro or R2 is OS(O)n2-R21, N(R23)-S(O)n3-R22, cyano, carbamoyl, C1-C4alkoxycarbonyl, formyl, halogen, thiocyanato, amino, hydroxy-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-S(O)n4-C1-C4alkyl, cyano-C1-C4alkyl, C1-C6alkylcarbonyloxy-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4alkoxycarbonyloxy-C1-C4alkyl, C1-C4thiocyanato-C1-C4alkyl, benzoyloxy-C1-C4alkyl, C2-C6oxiranyl, C1-C4alkylamino-C1-C4alkyl, di-(C1-C4-alkyl)amino-C1-C4alkyl, C1-C12alkylthiocarbonyl-C1-C4alkyl or formyl-C1-C4alkyl, or R2 is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)-, —CH2SO—, or -CH2SO2 group and it not being possible for each ring system to contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C6acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen; R3 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C6alkylamino, C2-C6dialkylamino, C1-C6alkylaminosulfonyl, C2-C6dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or R3 is —N(R23)—S(O)n—R22, cyano, halogen, amino, C1-C4alkoxy-C1-C4alkyl or C1-C4alkyl-S(O),-C1-C4alkyl; R4 is hydrogen, C1-C6alkyl, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6haloalkenyloxy, C3-C6alkynyloxy, C1-C4alkylcarbonyloxy, C1-C4alkylsulfonyloxy, tosyloxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C1-C4dialkylamino, C1-C4alkoxycarbonyl, C1-C4haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; or R4 is a five to ten-membered monocyclic or R3-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system, unless fused, being bonded to the pyridine ring directly or via a C1-C4alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)—, —CH2S—, —CH2SO—, or —CH2SO2— group and it not being possible for the ring system to contain more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C4alkoxy-C1-C2alkylthio, C1-C4alkylcarbonyl-C1-C2alkylthio, C1-C4alkoxycarbonyl-C1-C2alkylthio, cyano-C1-C4alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen;

[0008] R21 is C1-C4alkyl or C1-C4haloalkyl;

[0009] R22 is C1-C4alkyl, C1-C4haloalkyl or di-(C1-C4alkyl)amino;

[0010] R23 R24, R25 independently of one another are hydrogen or C1-C4alkyl;

[0011] n, n1, n2, n3 and n4 independently of one another are 0, 1 or 2;

[0012] Q is Q1 3embedded image

[0013] in which

[0014] R6, R7, R8 and R9 independently of one another are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkyl-S(O)n17, C1-C6alkyl-NHS(O)2, C1-C6alkylamino, di-(C1-C6alkyl)amino, hydroxyl, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, hydroxy-C1-C6alkyl, C1-C4alkylsulfonyloxy-C1-C6alkyl, tosyloxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkyl-S(O),4-C1-C6alkyl, cyano-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy, benzyloxy-C1-C6alkyl, C1-C6alkoxycarbonyl-C1-C6alkyl, C1-C6alkoxycarbonyloxy-C1-C6alkyl, thiocyanato-C1-C6alkyl, oxiranyl, C1-C6alkylamino-C1-C6alkyl, di(C1-C6alkyl)amino-C1-C6alkyl, formyl-C1-C6alkyl, C1-C6alkyloximo, halogen, cyano, nitro, phenyl or phenyl which is substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n18, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n5, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)n19N(C1-C4alkyl)2, halogen, nitro, COOH or cyano;

[0015] or adjacent R6 and R7 or R8 and R9 together are —(CH2)m—, C(O)O(CH2)n20— or —S(O)n21(CH2)n22—;

[0016] n5, n17, n18, n19 and n21 independently of one another are 0, 1 or 2;

[0017] n20 is 2 or 3;

[0018] n22 is 2,3 or 4;

[0019] m is 2, 3, 4, 5, or 6;

[0020] W is oxygen, S(O)n6, —CR11R12, —CR63R64CR65R66, —C(O)— or —NR13;

[0021] R63, R64, R65 and R66 independently of one another are hydrogen or C1-C6alkyl, or R65 together with R7 or R9 forms a direct bond;

[0022] n6 is 0, 1 or 2;

[0023] R11 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylthio-C3-C6cycloalkyl, C1-C4alkycarbonyloxy-C1-C4alkyl, C1-C4alkysulfonyloxy-C1-C4alkyl, tosyloxy-C1-C4alkyl, di-(C1-C3alkoxyalkyl)methyl, di-(C1-C3alkthioalkyl)methyl, (C1-C3alkoxyalkyl)-(C1-C3alkthioalkyl)methyl, C3-C5oxacycloalkyl, C3-C5thiacycloalkyl, C3-C4dioxacycloalkyl, C3-C4dithiacycloalkyl, C3-C4oxathiacycloalkyl, formyl, C1-C4alkoxycarbonyl, carbamoyl, C1-C4alkylaminocarbonyl, di-(C1-C4alkyl)aminocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl or phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n21, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n7, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)n20N(C1-C4alkyl), halogen, nitro, COOH or cyano;

[0024] n7, n20 and n21 independently of one another are 0, 1 or 2;

[0025] or R12 together with R6 or R9 is a group —(CH2)o—;

[0026] o is 1, 2, 3, 4 or 5;

[0027] R12 is hydrogen, C1-C4alkyl or C1-C4haloalkyl;

[0028] or R12 together with R11 is a group -(CH2)mI; m1 is 2, 3, 4, 5, or 6; R10 is hydroxyl, O-M+, halogen, cyano, SCN, OCN, C1-C12alkoxy, C1-C4alkoxycarbonyl-C1-C4alkoxy, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C2alkylsulfonyl, C1-C12haloalkylthio, C1-C12haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C6alkoxy-C1-C6alkylthio, C1-C6alkoxy-C1-C6alkylsulfinyl, C1-C6alkoxy-C1-C6alkylsulfonyl, C2-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12haloalkenylsulfonyl, C1-C4-alkoxycarbonyl-C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkylsulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, (C1-C4alkoxy)2P(O)O, C1-C4alkyl-(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, R14R15N, R14R15NNH, R16R17NC(O)O—, R16R17NC(O)NH—, C1-C12alkyl-S(O)2NR18, C1-C4haloalkyl-S(O)2NR19, C1-C12alkyl-S(O)2O, C1-C4haloalkyl-S(O)2O, C1-C18alkylcarbonyloxy, it being possible for the alkyl group to be substituted by halogen, C1-C6alkoxy, C1-C6alkylthio or cyano, or is C2-C18alkenylcarbonyloxy, C2-C18alkynylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylthiocarbonyloxy, C1-C12alkylthiocarbamoyl, C1-C6alkyl-NH(CS)N(C1-C6alkyl)-N H-, di-C1-C6alkyl-N(CS)N(C1-C6alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano; or R10 is a group Ar1-thio, Ar2-sulfinyl, Ar3-sulfonyl, —OCO—Ar4or NH—Ar5in which Ar1, Ar2, Ar3, Ar4 and Ar5 independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, and it being possible for each ring system to contain not more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C16alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen;

[0029] R14, R15, R16, R17 and R18 independently of one another are hydrogen or C1-C6alkyl;

[0030] n8, n9, n10, n11, n12, n13and n14 independently of one another are 0, 1 or 2;

[0031] R13 is hydrogen, C1-C4alkyl, C1-C4alkythio-C1-C4carbonyl, C1-C4alkylsulfinyl-C1-C4carbonyl, C1-C4alkylsulfonyl-C1-C4carbonyl, C1-C4alkoxycarbonyl, C1-C4alkylcarbonyl, phenylcarbonyl, or is phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4-alkylamino, C1-C4alkyl-S(O)n15, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)nl6, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro, or cyano; and

[0032] n15 and n16 independently of one another are 0, 1 or 2;

[0033] and the agrochemically tolerated salts M+and all stereoisomers and tautomers of the compounds of the formula I.

[0034] The alkyl groups in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the abovementioned alkyl radicals. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

[0035] An alkylene group for example, —(CH2)m—, —(CH2)m1— or —(CH2)o— can be substituted by one or more methyl group; preferably, such alkylene groups are in each case unsubstituted. The same also applies to the —C(O)O(CH2)20— and —S(O)n21(CH2)n22— group and to all C3-C6-cycloalkyl-, C3-C5oxacycloalkyl-, C3-C5thiacycloalkyl-, C3-C4dioxacycloalkyl-, C3-C4-dithiacycloalkyl-, C3-C4oxathiacycloalkyl-containing groups.

[0036] Halogen is, as a rule, fluorine, chlorine, bromine or iodine. This also applies analogously to halogen in conjunction with other meanings such as haloalkyl or halophenyl.

[0037] Haloalkyl groups with a chain length of 1 up to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chioroethyl, 2-fluoroprop-2-yl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, pentafluoroethyl, heptafluoro-n-propyl, perfluoro-n-hexyl; haloalkyl groups in the meanings R2, R3 and, in particular, R5 are preferably trichloromethyl, fluoromethyl, dichlorofluoromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoro-n-propyl.

[0038] Suitable as haloalkyl are monohalogenated or polyhalogenated alkenyl groups, where halogen is fluorine, chlorine, bromine and iodine, and in particular fluorine and chlorine, for example 1-chlorovinyl, 2-chlorovinyl, 2,2-difluorovinyl, 2,2-difluoroprop-1-en-2-yl, 2,2-dichlorovinyl, 3-fluoroprop-1-enyl, chloroprop-1-en-1-yl, 3-bromoprop-1-en-1-yl, 2,3,3-trifluoroprop-2-en-1-yl, 2,3,3-trichloroprop-2-en-1-yl and 4,4,4-trifluorobut-2-en-1-yl. Preferred amongst the monohalogenated, dihalogenated or trihalogenated C2-C6alkenyl groups are those which have a chain length of 2 to 5 carbon atoms.

[0039] Suitable as haloalkynyl are, for example, monohalogenated or polyhalogenated alkynyl groups, where halogen is bromine, iodine and, in particular, fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluorobut-2-yn-1-yl. Preferred amongst the monohalogenated or polyhalogenated alkynyl groups are those which have a chain length of 2 to 5 carbon atoms.

[0040] A monohalogenated or polyhalogenated C3-C6cycloalkyl group is, for example, the 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2,3,3-tetrafluorocyclobutyl or 2,2-difluoro-3,3-dichlorocyclobutyl group.

[0041] Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy and the pentyloxy and hexyloxy isomers; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl, ethoxycarbonyl or tert-butoxycarbonyl. Haloalkoxy groups preferably have a chain length of 1 to 6 carbon atoms.

[0042] Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichioroethoxy; preferably fluoromethoxy, difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

[0043] Alkylthio groups preferably have a chain length of 1 to 8 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl.

[0044] Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.

[0045] Alkylamino is, for example, methylamino, ethylamino, n-propylamino, iso-propylamino or the butylamino isomers. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, di-butylamino and di-iso-propylamino. Preferred are alkylamino groups having a chain length of 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, iso-propoxymethyl or iso-propoxyethyl. Alkylthioalkyl groups preferably have 1 to 6 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, iso-propylthiomethyl, iso-propylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl.

[0046] Phenyl, also as part of a substituent such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl or tosyl can be in monosubstituted or polysubstituted form. In this case, the substituents can be in any of the ortho, meta and/or para position(s).

[0047] Allenyl is, for example, CH2═C═CH2 CH2═CH—CH2—CH═CH2, CH2═CH—CH2—CH2—CH═CH2 or CH2═CH—CH2—CH═CH—CH3.

[0048] The invention also extends to the salts M+ which the compounds of the formula 1, in particular those compounds of the formula I in which R10 is O−M+, can form, preferably with amines, alkali metal bases, alkaline earth metal bases or quaternary ammonium bases. The following must be emphasized as salt formers amongst the alkali metal bases and alkaline earth metal bases: the hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular those of sodium or potassium. Examples of amines which are suitable for ammonium salt formation are not only ammonia, but also primary, secondary and tertiary C1-C18alkylamines, C1-C4hydroxyalkylamines and C2-C4alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso-propylamine, the four butylamine isomers, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methyinonylamine, methyl-pentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, iso-propanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines for example, pyridine, quinoline, iso-quinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines for example anilines, methoxyanilines, ethoxyanilines, o-, m-, p-toluidines, phenylenediamines, naphthylamines and o-, m- and p-chloroanilines; but in particular triethylamine, iso-propylamine and di-iso-propylamine. Examples of quaternary ammonium bases which are suitable for salt formation are, for example, [N(Ra Rb Rc Rd)]+OH−, where Ra, Rb, Rc and Rd independently of one another are C1-C4alkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions. M+preferably represents an ammonium salt, in particular NH4+, or an alkali metal, in particular potassium or sodium.

[0049] The compounds of the formula I can occur in various tautomeric forms, for example, if R10 is hydroxyl, in the preferred formulation I′ and I′″ 4embedded image

[0050] Preferred among the compounds of the formula I are those in which

[0051] p is 0;

[0052] R5 is C1-C6haloalkyl;

[0053] R2 is hydrogen, C1-C6alkyl, CG-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6-alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, benzyi-S(O)n1-, C1-C6alkylamino, C2-C6dialkylamino, C1-C6-alkylaminosulfonyl, C2-C6-dialkylaminosulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl group, in turn, to be substituted by C1-C3-alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or is OS(O)n2—R21, N(R23)—S(O)n3—R22, cyano, halogen, amino, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-S(O)n4-C1-C4alkyl, cyano-C1-C4alkyl or C1-C4alkoxy-C1-C4alkoxy; R3 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6-alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6alkylamino, C2-C6dialkylamino, C1-C6alkylaminosulfonyl, C2-C6-dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or is —N(R23)—S(O)n—R22, cyano, halogen, amino, C1-C4alkoxy-C1-C4alkyl or C1-C4alkyl-S(O)n—C1-C4alkyl;

[0054] R4 is hydrogen, C1-C6alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyloxy, C1-C4-alkylthio, C1-C4alkylsuffinyl, C1-C4alkylsulfonyl, C1-C4haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; or R4 is a five- to ten-membered monocyclic or R3-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4alkylene group and it not being possible for the ring system to contain more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6-Alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C4-alkoxy-C1-C2alkylthio, C1-C4alkylcarbonyl-C1-C2alkylthio, C1-C4alkoxycarbonyl-C1-C2alkylthio, iro, cyano-C1-C4alkylthio, C1-C6alkylsultinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen;

[0055] R21 and R22 independently of one another are C1-C4alkyl or C1-C4haloalkyl;

[0056] R23 R24 and R25 independently of one another are hydrogen or C1-C4alkyl;

[0057] n, n1, n2, n3 and n4 independently of one another are 0, 1 or 2;

[0058] Q is Q1 5embedded image

[0059] in which

[0060] R6, R7, R8 and R9 independently of one another are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxycarbonyl, C1-C6alkyl-S(O)n17, C1-C6alkyl-NHS(O)2, C1-C6alkylamino, di-(C1-C6alkyl)amino, hydroxyl, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6-alkynyloxy, hydroxy-C1-C6alkyl, C1-C4alkylsulfonyloxy-C1-C6alkyl, tosyloxy-C1-C6alkyl, halogen, cyano, nitro, phenyl or phenyl which is substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4aikoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4-alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n18, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n5, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NlH, C1-C4alkyl-S(O)ng9N(C1-C4alkyl), halogen, nitro, COOH or cyano;

[0061] or adjacent R6 and R7 or R8 and R9 together are —(CH2)m—;

[0062] n5 n17, n18 and n19 independently of one another are 0, 1 or 2;

[0063] m is 2, 3, 4, 5, or 6 ;

[0064] W is oxygen, S(O)n6, —CR11R12—, —C(O)— or —NR13—;

[0065] n6 is 0, 1 or 2;

[0066] R11 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylcarbonyloxy-C1-C4alkyl, C1-C4alkylsulfonyloxy-C1-C4alkyl, tosyloxy-C1-C4alkyl, di-(C1-C3alkoxyalkyl)methyl, di-(C1-C3alkylthioalkyl)methyl, (C1-C3alkoxyalkyl)-(C1-C3alkylthioalkyl)methyl, C3-C5oxacycloalkyl, C3-C5thiacycloalkyl, C3-C4dioxacycloalkyl, C3-C4-dithiacycloalkyl, C3-C4oxathiacycloalkyl, formyl, C1-C4alkoxycarbonyl or phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4aikoxy, C1-C4haloalkoxy, C1-C4-alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C -C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n21, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n7, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)n20N(C1-C4alkyl), halogen, nitro, COOH or cyano;

[0067] n7, n20 and n21 independently of one another are 0, 1 or 2;

[0068] or R12 together with R9 is a group —(CH2)o—;

[0069] o is 1, 2, 3, 4 or 5;

[0070] R12 is hydrogen, C1-C4alkyl or C1-C4haloalkyl;

[0071] or R12 together with R11 is a group —(CH2)m1;

[0072] m, is 2, 3, 4, 5, or 6;

[0073] R10 is hydroxyl, O−M+, halogen, C1-C12alkoxy, C1-C12alkylcarbonyloxy, C2-C4-alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12-alkylcarbonyloxy, R23R24N—C(O)O, C1-C12alkylS(O)n8—, C1-C4haloalkyl-S(O)n9—, C2-C12-alkenylS(O)n10—, C2-C12haloalkeny]S(O)n11—, C2-C12alkyny[S(O)n12—; benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl group, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n13, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n14, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano, or is C1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4-alkoxy)2P(O)O, C1-C4alkyl(C1-C4alkoxy)P(O)O, or H(C1-C4alkoxy)P(O)O;

[0074] n8, n9, n10, n11, n12, n13 and n14 independently of one another are 0, 1 or 2;

[0075] R13 is hydrogen, C1-C4alkyl, C1-C4alkoxycarbonyl or phenyl which, in turn, can be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n15, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n16, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano;

[0076] n15 and n16 independently of one another are 0, 1 or 2;

[0077] and the agrochemically tolerated salts M+ and all stereoisomers and tautomers of the compounds of the formula I.

[0078] In a preferred group of compounds of the formula 1, RI0 is halogen, thiocyanato, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylthio, C1-C12-haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12-alkenylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12-haloalkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C1-C4alkoxycarbonyl-C1-C2alkylthio, C1-C4alkoxycarbonyl-C1-C2alkylsulfinyl, C1-C4alkoxycarbonyl-C1-C2alkylsutfonyl, C1-C8alkyl-S(O)2NH, C1-C8haloalkyl-S(O)2NH, C1-C8alkyl-S(O)2O, C1-C18alkylcarbonyloxy, C2-C18alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12-alkylthiocarbonyloxy, R16R17NC(O)O—, R16R17NC(S)O—, benzylthio, benzylsulfinyl, benzylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted as indicated in claim 1; or is a group Ar1-thio, Ar1-sulfinyl, Ar1-sulfonyl in which Ar1 is a five- or six-membered monocyclic ring system which can be aromatic or partially saturated and can contain 1 to 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and which, in turn, can be substituted as indicated in claim 1; or is thienylcarbonyloxy or furylcarbonyloxy, it being possible for these, in turn, to be substituted by methyl or halogen, or pyridylcarbonyloxy which, in turn, can be substituted as indicated in claim 1.

[0079] In preferred compounds of the formula 1, furthermore, R10 is hydroxyl or O−M+.

[0080] Other compounds of the formula I which must be emphasized are those in which W is oxygen, —CR11R12— or —C(O)—, where, in particular when W is —CR11R12—,

[0081] a) R6 is hydrogen, methyl, ethyl, cyano, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or methoxy; and R7, R8, R9, R11 and R12 independently of one another are hydrogen, C1-C4alkyl, C1-C3haloalkyl, C2-C3alkenyl or C2-C3alkynyl, or

[0082] b) adjacent R6 and R7 and/or R8 and R9 together are —(CH2)m—, —C(O)O(CH2)2— or S(O)n21(CH2)3—; or

[0083] c) R6 is hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or methoxy and R12 together with R9 is —(CH2)o—.

[0084] Furthermore, preferred groups of compounds of the formula I are those in which W is oxygen and R6, R7, R8 and R9 independently of one another are hydrogen or C1-C3alkyl; or

[0085] W is —C(O)— and R6, R7, R8 and R9 independently of one another are C1-C3alkyl; or

[0086] R2 is hydrogen and R3 is methyl; or

[0087] R2 is methyl, ethyl, n-propyl, i-propyl, vinyl, methoxymethyl, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, acetoxymethyl, propionyloxymethyl, chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl or cyanomethyl.

[0088] Other compounds of the formula I which must be emphasized are those in which R4 is hydrogen or methyl or R5 is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoropropyl or difluoromethyl.

[0089] In a further preferred group of compounds of the formula I, R3 is hydrogen, R2 is C1-C4alkyl, FC-C3haloalkyl, cyclopropyl, C2-C3alkenyl, C2-C3haloalkenyl, C2-C3alkynyl, allenyl, C1-C2-alkoxy-C1-C2alkyl, C1-C2alkylthio-C1-C2alkyl, cyano-C1-C2alkyl, C1-C2alkoxycarbonyl-C1-C2-alkyl, C1-C4alkylcarbonyloxy-C1-C2alkyl, C1-C3alkoxy, C1-C3haloalkoxy, allyloxy, propargyloxy, C1-C3alkylthio, C1-C3alkylsulfinyl or cyano.

[0090] The compounds of the formula I in which Q is a group Q1 can be prepared using processes which are known per se, for example those described in EP-A-0 353 187 and EP-A-0 316 491, for example either by

[0091] a) reacting a compound of the formula III 6embedded image

[0092] in which R2, R3, R4 and R5 have the meaning given under formula I and X is a leaving group, for example halogen or cyano, with a compound of the formula II 7embedded image

[0093] in which R6, R7, R8, R9 and W have the meaning given under formula I in the presence of a base and in an inert organic solvent to give the compound of the formula 8embedded image

[0094] and subsequently isomerizing the latter, for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a cyanide source; or

[0095] b) reacting a compound of the formula XVI 9embedded image

[0096] in which R2, R3, R4 and R5 have the meaning given under formula I with compounds of the formula II 10embedded image

[0097] in which R6, R7, R8, R9 and W have the meaning given under formula I in an inert organic solvent in the presence of a base and a coupling agent to give the compound of the formula IV 11embedded image

[0098] and subsequently isomerzing the latter, for example as described under route a). The preparation of the compounds of the formula I is illustrated in greater detail in reaction scheme 1 below. 12embedded image

[0099] The compounds of the formula I with the group Q1 in which R10 is hydroxyl can preferably be prepared in accordance with this reaction scheme. The starting material for the preparation of the compounds of the formula I in which Q is the group Q1 and R10 is hydroxyl is, in accordance with reaction scheme 1, route a), the carboxylic acid derivatives of the formula III in which X is a leaving group for example halogen, for example iodine, bromine and, in particular chlorine, N-oxyphthalimide or N,O-dimethythydroxylamino or part of an activated ester, for example 13embedded image

[0100] (formed from dicyclohexylcarbodiimide (DGC) and the corresponding carboxylic acid) or 14embedded image

[0101] (formed from N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (EDC) and the corresponding carboxylic acid). These are reacted with the dione derivatives of the formula It in an inert organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, and in the presence of a base, for example an alkylamine, preferably triethylamine, an aromatic amine, for example pyridine or 4-dimethylaminopyridine (DMAP) to give the isomeric enol ethers of the formula IV. This esterification is successfully carried out at temperatures from 0° C. to 110° C.

[0102] The isomerization of the ester derivatives of the formula IV to give the dione derivatives of the formula I (in which R10 is OH) can be carried out, for example, in analogy to EP-A-0 353 187 or EP-A-0 316 491 in the presence of a base, for example an alkylamine, for example triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP or a catalytic amount of a cyanide source, for example acetone cyanohydrin or potassium cyanide. Both reaction steps can be carried out in situ without isolation of the intermediates IV, in particular when using a cyanide compound of the formula III (X=cyano), or in the presence of a catalytic amount of acetone cyanohydrin or potassium cyanide.

[0103] In accordance with reaction scheme 1, route b), the desired diones of the formula I (in which R10 is hydroxyl) can be obtained, for example, analogously to Chem. Lett. 1975, 1045 by esterifying the carboxylic acids of the formula XVI with the dione derivatives of the formula II in an inert solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile or an aromatic hydrocarbon, e.g. toluene, in the presence of a base, for example an alkylamine, e.g. triethylamine, and a coupling agent, for example 2-chloro-1-methylpyridinium iodide. Depending on the solvent used, this esterification is successfully carried out at temperatures from 0° C. to 110° C. and first yields, as described under route a), the isomeric ester of the formula IV which can be isomerized as described under route a), for example in the presence of a base and a catalytic amount of DMAP, or a cyanide source, to give the desired dione derivatives of the formula I (R10=hydroxyl).

[0104] The activated carboxylic acid derivatives of the formula III in reaction scheme I (route a) in which X is a leaving group, for example halogen, e.g. bromine, iodine or, in particular, chlorine, can be prepared by known standard methods, for example as described by C. Ferri “Reaktionen der organischen Synthese” [“Reactions in organic synthesis”], Georg Thieme Verlag, Stuttgart, 1978, page 460 et seq. This is shown in the reaction scheme 2 which follows. 15embedded image

[0105] In accordance with reaction scheme 2, the compounds of the formula III in which X has the abovementioned meaning are prepared, for example, by using a halogenating agent, for example thionyl halides, e.g. thionyl chloride or thionyl bromide; phosphorus halides or phosphorus oxyhalides, e.g. phosphorus pentachloride or phosphorus oxychloride, or phosphorus pentabromide or phosphoryl bromide; or oxalyl halides, for example oxalyl chloride, or by employing a reagent for forming activated esters, for example N,N′-dicyclohexylcarbodiimide (DCC) or N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (EDC), of the formula XVII Examples of meanings of X for the compound of the formula XVII as halogenating agent is a leaving group, for example halogen, e.g. fluorine, bromine or iodine and, in particular, chlorine, and W1 is, for example, PCl2, SOCI, SOBr or ClCOCO.

[0106] The reaction is preferably carried out in an inert organic solvent, for example in aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbons, e.g. n-hexane, benzene, toluene, xylenes, dichloromethane, 1,2-dichloroethane or chlorobenzene, at reaction temperatures in the range of −20° C. to the reflux temperature of the reaction mixture, preferably at 40-150° C., and in the presence of a catalytic amount of N,N-dimethylformamide. Such reactions are generally known, and various variations with regard to the leaving group X are described in the literature.

[0107] Compounds of the formula I in which R10 is other than hydroxyl or halogen can be prepared by conversion methods which are generally known from the literature, for example by acylation or carbamoylation methods using appropriate acid chlorides in the presence of a suitable base, starting from compounds in which R10 is hydroxyl, or can be prepared by nucleophilic substitution reactions on chlorides of the formula I in which R10 is halogen, which can also be obtained by known methods by reaction with a chlorinating agent such as phosgene, thionyl chloride or oxalyl chloride. In this case, examples of compounds which are employed are suitably substituted amines, or, directly, hydroxylamines, or alkylsulfonamides, mercaptans, thiophenols, phenols, Ar5-NH2 or Ar1-SH, in the presence of a base, for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.

[0108] Compounds of the formula I in which R10 contains thio groups can be oxidized in analogy to known standard methods, for example using peracids, e.g. meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formula I. The degree of oxidation on the sulfur atom (SO— or SO2—) can be controlled by the amount of oxidant.

[0109] Also, the resulting derivatives of the formula I in which R10 is other than hydroxyl can exist in various isomeric forms which, if appropriate, can be isolated in pure form. The invention therefore also extends to all of these stereoisomeric forms. Examples of these isomeric forms are the formulae I*, I** and I*** below in which Q is the group Q1 (see also note and scheme on page 10 above). 16embedded image

[0110] All other compounds from within the scope of the formula I can be readily prepared taking into consideration the chemical properties of the pyridyl or Q moiety.

[0111] The end products of the formula I can be isolated in the customary manner by concentration or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by means of column chromatography and a suitable eluent.

[0112] Furthermore, the skilled worker knows in which sequence certain reactions are expediently carried out to avoid any side reactions. Unless a directed synthesis for isolating pure isomers is carried out, the product may be obtained as a mixture of two or more isomers. The isomers can be resolved by methods known per se.

[0113] Compounds of the formula I in which n is 1, i.e. the corresponding N-oxides of the formula 1, can be synthesized by reacting a compound of the formula I in which n is 0 with a suitable oxidant, for example with the H2O2-urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride.

[0114] Compounds of the formula I in which R in the ortho-position relative to the pyridine nitrogen is 1-chloro-C1-C2alkyl, 1-hydroxy-C1-C2alkyl, 1-(C1-C6alkylcarbonyloxy)-C1-C2alkyl, 1-benzoyloxy-C1-C2alkyl, 1-(C1-C4alkoxycarbonyloxy)-C1-C2alkyl, 1-(C1-C4alkylthio)-C1-C2-alkyl, 1-(C1-C4alkylsuffinyl)-C1-C2alkyl, 1-(C1-C4alkylsulfonyl)-C1-C2alkyl, 1-thiocyanato-C1-C2alkyl, 1-cyano-C1-C2alkyl, can also be prepared by, for example, heating an N-oxide of the formula I under known reaction conditions, for example in the presence of tosyl chloride (see, for example, Parham, W. E.; Sloan, K. B.; Reddy, K. R.; Olson, P. E.; J Org Chem 1973, 38, 927) or in the presence of an acid anhydride (see, for example, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.; Heterocycles 1986, 24, 2169) and, if appropriate, subsequently further reacting the product. These reaction sequences.may be demonstrated with reference to the following example: 17embedded image

[0115] Compounds of the formula I in which R in the ortho-position relative to the pyridine nitrogen, in particular 1-bromo-C1-CIkyl, 1-chloro-C1-C2alkyl, 1-fluoro-C1-Calkyl, 1,1-dibromomethyl, 1,1-dichloromethyl, formyl, 1-(C1-C4alkylthio)-C1-C2alkyl, 1-(C1-C4alkylsulfinyl)-C1-C2alkyl, 1-(C1-C4alkylsulfonyl)-C1-C2alkyl, 1-thiocyanato-C1-C2alkyl or 1-cyano-C1-C2alkyl, can also be prepared, for example, by oxidizing a compound of the formula I in which R10 is, in particular, chlorine, C1-C4alkoxycarbonyloxy or benzoylcarbonyloxy under known halogenation conditions, for example with N-bromosuccinimide or N-chlorosuccinimide in the presence of light and a free-radical initiator, for example benzoyl peroxide, to give the 1-bromo or 1-chloro, 1,1-dibromo or 1,1-dichloro compound, and subsequently refunctionalizing the latter to give the corresponding derivatives. Again, these reaction sequences may be demonstrated with reference to the example below. 18embedded image

[0116] Compounds of the formula I can also be synthesized by reacting a compound of the formula I in which p is 0 and R2 is C1-C6alkyl with a suitable base, for example lithium diisopropylamide or n-butyllithium, at temperatures between −100 and -20° C. (preferably −70 and −50° C.) in an inert solvent (for example tetrahydrofuran) to give the corresponding dianion. The skilled worker knows how such carbanions can be converted by means of electrophilic substitution, for example with a chloroformic ester. This reaction sequence may be demonstrated with reference to the following example: 19embedded image

[0117] Other compounds from within the scope of the formula I can be prepared with suitable electrophiles taking into consideration the chemical properties of the pyridyl or Q moiety.

[0118] The compounds of the formula IIIa 20embedded image

[0119] in which

[0120] R501 is C1-C6haloalkyl;

[0121] R301 is hydrogen;

[0122] R401 is hydrogen or C1-C6alkyl; and

[0123] R201 is C1-C6alkyl, C1-C6haloalkyl-C1-C4alkyl, C2-C6alkenyl, C2-C6haloalkenyl, or C1-C2-alkoxycarbonyl- or phenyl-substituted vinyl, C2-C6alkynyl or C2-C6haloalkynyl; or trimethylsilyl-, hydroxyl-, C1-C2alkoxy-, C1-C2alkoxycarbonyl- or phenyl-substituted ethynyl or C3-C6allenyl; or C3-C6cycloalkyl, halogen-substituted C3-C6cycloalkyl, C1-C4alkoxy-C1-C4-alkyl, C1-C4alkyl-S(O),-C1-C4alkyl, cyano-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4-thiocyanato, oxiranyl, C1-C4alkylamino-C1-C4alkyl, C1-C4dialkylamino-C1-C4alkyl, hydroxy-C1-C4alkyl, C1-C12alkylthiocarbonyl-C1-C4alkyl or formyl-C1-C4alkyl, or R201 is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C1-C4-alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)-, —CH2S—, —CH2SO— or —CH2SO2-group and it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6-alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are other than halogen; and X is halogen or cyano, are novel and were developed specifically for the preparation of the compounds of the formula I and are therefore a further subject of the present invention.

[0124] The compounds of the formula XVIa 21embedded image

[0125] in which R201, R301, R401 and R501 have the abovementioned meaning, with the proviso that, if R501 is trifluoromethyl and, simultaneously, R301 and R401 are hydrogen, then R201 is other than C1-C6alkyl, are novel and therefore a further subject of the present invention.

[0126] The compounds of the formula Q1 (or formula II) are known and can be prepared by methods similar to those described, for example in J. Org. Chem. (1977), 42, 1163-9, Brit. UK Pat. Appl.GB 2205316, DE 3902818, GB 8706557, DE 4434987, WO 9213821 and Aust. J. Chem. (1976), 29(11), 2525-31, Chem. Commun. (1998), (16), 1691-1692.

[0127] The compounds of the formula XVI (or XVIa and XVIb) are synthesized by methods similar to known methods, for example as in Heterocycles, 46, 129 (1997) or Helvetica Chimica Acta 71, 596 (1988), and is characterized in that either

[0128] a) a compound of the formula V 22embedded image

[0129] in which R301 is hydrogen;

[0130] R401 is hydrogen, C1-C6alkyl or phenyl, it being possible for phenyl, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro;

[0131] or R401 is a five- to ten-membered monocyclic or fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and it not being possible for the ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C4alkoxy-C1-C2alkylthio, C1-C4alkylcarbonyl-C1-Calkylthio, C1-C4alkoxycarbonyl-C1-C2-alkylthio, cyano-C1-C4alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; and

[0132] R14 is C1-C4alkyl;

[0133] is acylated with a compound of the formula VI 23embedded image

[0134] in which R501 is C1-C6haloalkyl to give the compound of the formula VII 24embedded image

[0135] in which R301, R401, R501 and R14 have the abovementioned meaning in the presence of a base, for example an aromatic amine, e.g. pyridine, and the alkoxy group is subsequently exchanged for the amino group with ammonia in an organic solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile. The resulting compound of the formula VIII 25embedded image

[0136] is subsequently subjected to a condensation reaction with a compound of the formula IX 26embedded image

[0137] in which R201 is C1-C6alkyl, C1-C6haloalkyl-C1-C4alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6-alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-S(O)n4-C1-C4-alkyl, cyano-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4alkoxycarbonyloxy-C1-C4alkyl, C1-C4thiocyanato-C1-C4alkyl, oxiranyl, C1-C4alkylamino-C1-C4alkyl, di-(C1-C4alkyl)amino-C1-C4alkyl or formyl-C1-C4alkyl;

[0138] or R201 is a group Ar6—C1-C4alkyl in which Ar6 is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6-alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyt, C1-C6alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen, and R14 has the abovementioned meaning, and subsequently hydrolysing the resulting compound of the formula Xa 27embedded image

[0139] is subsequently hydrolysed to give the compound of the formula XVIa 28embedded image

[0140] in which R201, R301, R40, and R501 have the abovementioned meaning; or

[0141] b) a compound of the formula XI 29embedded image

[0142] in which R14 has the abovementioned meaning is subjected to a condensation reaction with a compound of the formula XII 30embedded image

[0143] and the resulting compound of the formula XIII 31embedded image

[0144] in which R3, R4 and R5have the abovementioned meaning and R14 is C1-C4alkyl, is chlorinated to give the compound of the formula XIV 32embedded image

[0145] in which R3, R4, R5 and R14 have the abovementioned meaning (for example using POCl3), and this compound is subsequently reacted with a nucleophile of the formula XV

Z—R15 (XV)

[0146] in which Z is SH, OH or amino and R15 is C1-C6alkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6-alkynyl, C3-Cohaloalkynyl, C1-C6alkylsulfonyl, C1-C6haloalkyl, phenyl or benzyl, it being possible for the phenyl group, in turn, to be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, or is C1-C4alkoxy-C1-CG4a)kyl, C1-C4-alkylthio-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl, C1-C4-alkylsulfonyl or di-(C1-C4alkyl)aminosulfonyl, or R15 is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6-haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6-haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-Cralkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, (CH2),R7, NR8R9, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen, in the presence of a base to give compounds of the formula Xb 33embedded image

[0147] in which R14, R15, R3, R4, R5 and Z have the abovementioned meanings and the resulting compound is subsequently hydrolysed to give the compound of the formula XVIb 34embedded image

[0148] in which R15, R3, R4, R5 and Z have the abovementioned meaning.

[0149] Compounds in which Z-R1l and Z are oxygen and R15 is C1-C6alkyl, C3-C6alkenyl, C3-C6-alkynyl, C1-C6haloalkyl, C3-C6haloalkenyl, cyano-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4-alkylthio-C1-C4alkyl or C1-C4alkoxycarbonyl-C1-C4alkyl can also be reacted starting from XIII by direct alkylation with the corresponding alkylating agent L-Rl5XVa in which L is a leaving group such as chlorine, bromine, iodine, mesyloxy or tosyloxy.

[0150] Compounds of the formula XVIb in which Z-R15 is fluorine are prepared by reacting a compound of the formula XIV with potassium fluoride and, if appropriate, a catalytic amount of 18-crown-6 in the presence of a polar aprotic solvent, for example acetonitrile, dimethylformamide or sulfolane. Compounds of the formula XVIc in which Z-R15 is hydrogen are prepared by reducing the chlorine group in formula XIV, for example with hydrogen in the presence of a suitable metal catalyst or with ammonium formate, in a suitable solvent. The preparation of the compounds of the formula XVI or XVIa, XVIb and XVIc are illustrated in greater detail in reaction schemes 3 and 4 which follow. 35embedded image 36embedded image

[0151] Compounds of the formula XVId in which R2 is bromomethyl, cyanomethyl, thiocyanatomethyl, C2-C6alkenyl, C2-C6haloalkenyl, a C1-C2alkoxycarbonyl- or phenyl-substituted vinyl, C2-C6alkynyl, C2-C6haloalkynyl, a trimethylsilyl-, hydroxyl-, C1-C2alkoxy-, C1-C2alkoxycarbonyl- or phenyl-substituted ethynyl, C3-C6allenyl, C3-C6cycloalkyl or mono or polyhalogenated C3-C6cycloalkyl can be prepared, for example, in accordance with generally known conversion methods which are shown in reaction scheme 4a. 37embedded image

[0152] Intermediates of the formula XVIa in which R501 is CF2Cl are prepared as described in scheme 3 or by reacting a compound of the formula Xa in which R501 is trichloromethyl with hydrofluoric acid in a pressurized vessel at temperatures between 0 and 220° C. (preferably 60-200° C.).

[0153] Compounds of the formula XVia in which R501 is CHF2 can be prepared as in scheme 3 or by heating a compound of the formula Xa in which R301, R401, R14 and R201 have the abovementioned meaning and R501 is CF2Cl in an inert solvent, for example toluene or benzene, at temperatures between 25 and 120° C. (preferably 80-120° C.) with tributyltin hydride or 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane in the presence of a catalytic amount of azo-isobutyronitrile and subsequently hydrolysing the resulting compound to give the compound of the formula XVIa in which R501 is CHF2.

[0154] Compounds of the formula XVIa in which R201, R301, R40, and R501 have the abovementioned meaning can also be prepared by reacting a compound of the formula Xc in which R14, R301, R401 and R501 have the abovementioned meaning and R201 is CH2Cl by nucleophilic substitution, for example with an alkali metal iodide in an inert solvent, to give the corresponding iodides, or by means of gaseous hydrobromic acid in lower carboxylic acids such as glacial acetic acid to give the corresponding bromine derivatives (for example in accordance with U.S. Pat. No. 3,974,166) or by means of alkali metal fluoride in a dipolar solvent such as sulfolane to give the corresponding fluorine derivatives, or, to prepare an alkoxy radical Xd, by reacting a halogen derivative Xc with an alcohol or phenol in the presence of a base such as sodium hydride or an alkaline earth metal oxide or alkaline earth metal carbonate or directly with an alkali metal alkoxide in an inert solvent such as dimethylformamide or in an excess of the alcohol ROH which corresponds to the group to be introduced at temperatures between −5 and 160° C.,

[0155] or, in order to prepare a corresponding aromatic or aliphatic thioether Xe, by reacting, analogously to what has been said above, either the halide Xc with an aliphatic or aromatic thiol in the presence of a base such as sodium hydride or with an alkali metal salt of a thiol in an inert solvent at −10-150° C., or, in order to prepare corresponding sulfinyl or sulfonyl derivatives Xe, by carrying out the reaction with an oxidant such as m-chloroperbenzoic acid or sodium periodate or sodium perborate, with the temperature control known in the art, depending on the degree of oxidation (for example −30° C.-+50° C. for n=1) or −20° C.-+100° C. for n=2) in an inert solvent such as dichloromethane to give Xf,

[0156] or, in order to prepare cyanomethylene derivatives of the formula Xg, by reacting a halide of the formula Xc with an alkali metal cyanide or tetraalkylammonium cyanide or copper cyanide in an inert solvent such as dichloromethane, tetrahydrofuran or dimethylformamide at temperatures between 0° C. and 220° C.

[0157] The preparation of the compounds of the formula XVIa (R501=CF2Cl) and of the intermediates of the formulae Xc, Xd, Xe, Xf, and Xg are illustrated in greater detail in the reaction schemes 5, 6 and 7 which follow. 38embedded image 39embedded image 40embedded image

[0158] To prepare all other compounds of the formula X and XVI which are functionalized in accordance with the definition of R201 (Z-R15) to R501, a multiplicity of known standard methods are suitable, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of the preparation methods which are suitable depending on the properties (reactivities) of the substituents in the intermediates.

[0159] The reactions to give compounds of the formula I are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chiorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone. The reaction temperatures are advantageously between -20° C. and +120° C. In general, the reactions are slightly exothermic and, as a rule, they can be carried out at room temperature. To shorten the reaction time, or else to start the reaction, the mixture may be heated briefly to the boiling point of the reaction mixture. The reaction times can also be shortened by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene. However, inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate, may also be used as bases. The compounds of the formula I can be isolated in the customary manner by concentrating and/or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

[0160] All application methods which are conventionally used in agriculture, for example pre-emergence application, post-emergence application and seed treatment, as well as various methods and techniques, for example the controlled release of active ingredients, are suitable for the use according to the invention of the compounds of the formula I or of compositions comprising them. To this end, the active ingredient in solution is applied to mineral carriers for granules or to polymerized granules (urea/formaldehyde) and dried. If appropriate, an additional coating can be applied (coated granules), which allows the active ingredient to be released in a controlled manner over a specific period of time.

[0161] The compounds of the formula I can be employed as herbicides as such, i.e. as obtained from synthesis. However, they are preferably processed in the customary manner together with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. The application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, as well as the type of composition, are chosen to suit the intended aims and the prevailing circumstances.

[0162] The formulations, i.e. the compositions, preparations or products which comprise the active ingredient of the formula I or at least one active ingredient of the formula I and, as a rule, one or more solid or liquid formulation auxiliaries are prepared in the known manner, for example by intimately mixing and/or grinding the active ingredients together with the formulation auxiliaries, for example solvents or solid carriers. Furthermore, surface-active compounds (surfactants) may additionally be used when preparing the formulations. Examples of solvents and solid carriers are indicated for example in WO 97/34485 on page 6.

[0163] Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, non-ionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties.

[0164] Examples of suitable anionic, non-ionic and cationic surfactants are enumerated, for example, in WO 97/34485 on pages 7 and 8.

[0165] The surfactants conventionally used in the art of formulation which are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H., “Tensid-Taschenbuch” [“Surfactants Guide”], Carl Hanser Verlag, Munich[Vienna, 1981, and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81, are furthermore also suitable for preparing the herbicidal compositions according to the invention.

[0166] As a rule, the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated compositions are more preferred as commercially available goods, the end consumer uses, as a rule, dilute compositions. The compositions can also comprise further additives such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.

[0167] As a rule, the active ingredients of the formula I are applied to the plant or its environment at rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired action can be determined by experiments. It depends on the type of the action, the developmental stage of the crop plant and of the weed, and on the application (location, timing, method) and can, owing to these parameters, vary within wide limits.

[0168] The compounds of the formula I are distinguished by herbicidal and growth-inhibitory properties which allow them to be employed in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, rapeseed, maize and rice and for the non-selective control of weeds. Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicides by means of conventional plant breeding or by genetic engineering methods. The weeds to be controlled may be both mono- and dicotyledonous weeds such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, lpomoea, Chrysanthemum, Galium, Viola and Veronica.

[0169] The examples which follow illustrate the invention in greater detail without limiting it.

PREPARATION EXAMPLES

Example H1

Preraration of 3-hydroxy-4,4-dimethyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (compound A2-B24)

[0170] 6.68 g (0.0305 mol) of methyl 2-methyl-6-trifluoromethyinicotinate (prepared as described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/water (3:1 mixture), and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added portionwise at a temperature of 22° C. After 4 hours at 22° C., the reaction mixture is poured onto ethyl acetate and 2 N hydrochloric acid, and the organic phase is washed three times with water, dried with sodium sulfate and evaporated, and the residue is triturated with a small amount of hexane. After filtration, 5.69 g (90% of theory) of 2-methyl-6-trifluoromethyinicotinic acid of melting point 147-149° C. are obtained.

[0171] The resulting 2-methyl-6-trifluoromethyinicotinic acid (1.026 g, 0.005 mol) is dissolved in 20 ml of oxalyl chloride. Three drops of dimethylformamide are added and the mixture is refluxed for 1 hour. The mixture is then concentrated on a rotary evaporator and the residue (2-methyl-6-trifluoromethylnicotinoyl chloride) is taken up in 100 ml of methylene chloride. At a temperature of 0° C., 1.6 ml (0.0115 mol) of triethylamine and 0.7 g (0.005 mol) of 4,4-dimethylcyclohexane-1,3-dione are added. After 2 hours at a temperature of 22° C., the solvent is removed on a vacuum rotary evaporator, the residue which remains is dissolved in 55 ml of acetonitrile, and 0.15 ml (0.0016 mol) of acetone cyanohydrin and 0.79 ml (0.0057 mol) of triethylamine are added in order to subject the intermediate to a rearrangement reaction. After the reaction solution has been stirred for 4 hours at room temperature, it is evaporated. The syrup which remains is chromatographed on silica gel. Elution with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) gives a pale yellow viscous oil (Rf=0.39 on the abovementioned mixture as mobile phase), which is dissolved in dichloromethane and washed in succession with 75 ml of 5% hydrochloric acid and 75 ml of water. Evaporation to dryness of the organic solution which has been dried with Na2SO4 yields 1.05 g (63%) of pure 3-hydroxy-4,4-dimethyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonylwcyclohex-2-enone in the form of white crystals of melting point 75-77° C.

[0172] 1H NMR (d6-DMSO, 8 in ppm): 1.342, s, 6H: 2.088, t, J 9 Hz, 2H: 2.685, s, 3H: 2.982, t, J 9 Hz, 2H:8.030, d, J 81 Hz, 1H: 8.094, d, (J, 8.1 Hz), 1H.

Example H2

Preparation of 5-methyl-5-trifluoromethylcyclohexane-1,3-dione (Compound H-B1066)

[0173] 0.64 g of sodium were introduced into 40 ml of ethanol, and 3.23 ml of methyl acetoacetate and 4.9 g of isopropyl 4,4,4-trifluoro-3-methylbut-2-enoate were introduced, and the mixture was heated at the boil for 18 hours. After the mixture has been partitioned between dilute hydrochloric acid and ethyl acetate, the mixture is evaporated. The remaining unpurified methyl 2-methyl-4,6-dioxo-2-trifluoromethylcyclohexanecarboxylate is hydrolysed in a mixture of methanol and water at boiling point in the presence of 9.1 g of sodium hydroxide.

[0174] The mixture is subsequently acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallization (ethyl acetate), pure 5-methyl-5-trifluoromethylcyclohexane-1,3-dione of melting point 150-152° C. is obtained.

Example H3

Preparation of methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate (Example H-B1069)

[0175] A 30% solution of 35.8 g of sodium methoxide is introduced into 65 ml of dimethyl sulfoxide and, within 20 minutes, treated with a mixture of 16.7 g of 3-methyl-3-butene-2-one and 32.4 g of dimethyl methoxymalonate at a temperature of 30-35° C. The mixture is stirred for 1 hour at a temperature of 35° C., and is then acidified with hydrochloric acid and extracted repeatedly with dichloromethane. The organic phases are washed with water, dried and concentrated. Crystallization from hot ethyl acetate and hexane gives pure methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate of melting point 117-117.5° C.

Example H4

Preparation of Methyl 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate (compound A2-B1069)

[0176] 2.23 g of fresh 2-methyl-6-trifluoromethyinicotinoyl chloride are added to a mixture of 2.14 g of methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate and 2.02 g of triethylamine in 30 ml of acetonitrile. After approximately 30 minutes, 0.065 g of potassium cyanide is added and the mixture is stirred for 18 hours. At pH 2, the mixture is subsequently partitioned between water and ethyl acetate, dried over magnesium sulfate and evaporated. Filtration on silica gel (mobile phase ethyl acetatelmethanol/triethylamine 85:10:5) gives the pure methyl 2-hydroxy-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate as a viscous oil.

Example H5

Preparation of 3-hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone (Compound A2-B1070)

[0177] 1.4 g of methyl 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate in dioxane/water (5:3) are treated with 0.586 g of potassium hydroxide and the mixture is stirred for 3 hours. The mixture is then acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromatography analogously to Example H4. 3-Hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone is obtained as a viscous oil (according to 1H-NMR as a mixture of 3 tautomeric forms).

Example H6

5-Chloro-2,2, 6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-cyclohex-4-ene-1,3-dione (compound A2-B1105) and 6-[chloro-(2-methyl-6-trifluoromethyl-pyridin-3-yl)methylene]-2,2,4,4-tetramethylcyclohexane-1 ,3,5-trione

[0178] 7.0 g (55 mmol) of oxalyl chloride are introduced into 18.5 g (50 mmol) of 5-hydroxy-2,2,6,6-tetramethyi-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione (compound A2-B354), dissolved in 50 ml of dichloromethane; 5 drops of dimethylformamide are added, and the mixture is slowly heated up to boiling point. After approximately 30 minutes, after the evolution of gas has ceased, the mixture is evaporated and the product is crystallized by adding n-hexane. The main product obtained is pure 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-t,3-dione, m.p. 119.5-120° C. Further HPLC-separation of the mother liquor using 5-10% ethyl acetate in hexane gives the isomer 6-fchloro-(2-methyl-6trifluoromethylpyridine-3-yl)methylene]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione, m.p. 92.5-93° C.

Example H7

5-Chloro-2,2,6,6-tetramethyl-4-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1.3-dione (comDound A1210-B1105)

[0179] 1.94 g (5 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1 ,3-dione are treated in 20 ml of dichloroethane at a temperature of −10° C. with 0.94 g (10 mmol) of hydrogen peroxide/urea adduct and 1.89 g (9 mmol) of trifluoroacetic anhydride. The reaction mixture is warmed to room temperature, with stirring, and held for a further 4 hours at this temperature. The mixture is then partitioned between ethyl acetate and water of pH 5, washed with sodium chloride solution and evaporated. The residue which is filtered through silica gel is pure 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione of melting point 145.5-146° C.

Example H8

4-(2-Bromomethyl-6-trifluoromethylpyridine-3-carbony:4-5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (compound A1029-B1105)

[0180] 0.39 g (1 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione and 0.20 g (1.1 mmol) of N-bromsuccinimide are refluxed in the presence of a catalytic amount of dibenzoyl peroxide in 10 ml of carbon tetrachloride. After the reaction has subsided, the resulting succinimide is removed by filtration and the crude product is purified by column chromatography (mobile phase: ethyl acetate/hexane 1:4). This gives pure 4-(2-bromomethyl-6-trifluoromethylpyridine-3-carbonyl)-5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione of melting point 94.5-95° C.

Example H9

2-(2-Acetoxymethyl-6-trifluoromethylpyridine-3-carbonVi)-4,4,6,6-tetramethyl-3,5-dioxocyclohex-1-enyl acetate (compound A1099-B1107)

[0181] 0.4 g (1 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione (Example H7) is refluxed for 25 minutes in the presence of 3 ml of acetic anhydride. The mixture is then concentrated and partitioned between ethyl acetate and sodium bicarbonate solution at pH 6.5. The crude product, separated on silica gel (mobile phase: ethyl acetatelhexane 1:4) yields the pure 2-(2-acetoxymethyl-6-trifluoromethylpyridine-3-carbonyl)-4,4,6,6-tetramethyl-3,5-dioxocyclohex-1-enyl acetate as an oil; 1H-NMR (CDCl3): 7.98 d, CH, 7.72 d, CH, 5.62 s, CH2, 2.22 and 2.20 2x OAc, 1.58, s, 2x CH3, 1.44 ppm, s, 2x CH3.

Example H10

5-Hydroxy-2-methyl-4-(2-methyl-6-trifluoromethvipyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one (compound A2-D109) and 3-hydroxy-7-methyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohepta-2,6-dienone (compound A2-F5)

[0182] 0.82 g (2 mmol) of ethyl trans-5-hydroxy-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-oxobicyclo[4.1.0]hept-4-en-2-carboxylate (compound A2-Dl1 1)is stirred in a 2:1 mixture of dioxane/water together with 0.254 g (4.5 mmol) of potassium hydroxide at room temperature until all of the starting material is reacted. Then, ethyl acetate is added, the mixture is acidified to pH 3 using 4 N HCl, and the 2-phase mixture is then heated for approx. 1 hour at a temperature of 40° C. The aqueous phase which is saturated with sodium chloride is then separated off. The ethyl acetate extract is evaporated to dryness and the product is chromatographed on silica gel (mobile phase ethyl acetate/hexane 1:2). The 1 st fraction which is isolated is 3-hydroxy-7-methyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohepta-2,6-dienone as pure tautomer mixture, 1H-NMR (CDCl3): 17.72 and 17.08, 2s, OH, 7.6-7.45, 2 arom. H, 6.68 and 6.62, 2t, CH, 2.84, m, 2.63, m, 2.52, m, 4H, 2.62 and 2.54, 2s, CH3, 2.03 and 1.77 ppm, 2s, CH3. Subsequent elution with 100% ethyl acetate gives, as the 2nd fraction, the isomer and tautomer mixture of 5-hydroxy-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one, 1H-NMR (CDCl3): i.a. 17.62 and 17.48, 2s, OH, 7.6-7.45, 2 arom. H, 2.54, m, 2.48, 2s CH3, 1.22 and 1.14,2d, CH3, 1.00 to 0.05 ppm, 2H.

Example H11

5-Hydroxy-2-methanesulfinyl-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]lhept-4-en-3-one (compound A2-D114):

[0183] 0.87 g (2.3 mmol) of 5-hydroxy-2-methyl-2-methylsulfanyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one (compound A2-D113), dissolved in 8 ml of methanol, is warmed for 3 hours at a temperature of 50° C. in the presence of 0.56 g of sodium periodate. The mixture is then partitioned between ethyl acetate and sodium chloride solution, concentrated, and the crude product is purified by chromatography (mobile phase: ethyl acetate/methanol 19:1). Pure 5-hydroxy-2-methanesulfinyl-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3one is obtained as tautomer and isomer mixture of melting point 159.5-160° C.

Example H12

2-Prop-2-ynyloxy-6-trifluoromethylnicotinic Acid (Compound A1025):

[0184] 47 g (0.2 mot) of 2-oxo-6-trifluoromethyl-1,2-dihydropyridine-3-carboxylic acid, 20 ml (0.25 mol) of propargyi bromide and 43 9 (0.31 mol) of potassium carbonate are heated to a temperature of 75° C. in a mixture of 40 ml of dimethylformamide and 80 ml of acetonitrile in the presence of a catalytic amount of 18-crown-6 ether. After 5 hours, the mixture is partitioned between ethyl acetate and saturated sodium chloride solution. The crude product is filtered through a silica gel column using 15% ethyl acetate in hexane. The main component, which is obtained in the form of an oil, is the pure ethyl 2-prop-2-ynyloxy-6-trifluoromethylnicotinate; 1H-NMR (CDCl3): 8.31, d, CH, 7.38, d, CH, 5.13, d, CH2, 4.41, q, CH2, 2.48, t, CCH, 1.41 ppm, t, CH3.

[0185] 36.3 g (0.13 mol) of this product is stirred over a period of 16 hours with a solution of 11.5 g (0.17 mol) of potassium hydroxide in 50 ml of water and 50 ml of dioxane. After acidification and extraction with ethyl acetate, crystalline 2-prop-2-ynyloxy-6-trifluoromethyinicotinic acid is obtained; 1H-NMR (CDCl3): 10.0, b, OH, 8.53, d, CH, 7.44, d, CH, 5.22, d, CH2, 2.54 ppm, t, CCH.

Example H13

2-Methylthio-6-trifluoromethyinicotinic acid (compound Al 5)

[0186] 9.4 g (40 mmol) of 2-oxo-6-trifluoromethyl-1,2-dihydropyridine-3-carboxylic acid are introduced into a 1-molar solution of 21.7 g of phosphorus tribromide (80 mmol) in dichloromethane at a temperature of 35° C. Then, the solvent is distilled off and the reaction mixture is heated slowly to boiling point, approx. 175° C. After 18 hours, the mixture is cooled to 0° C., diluted with dichloromethane and stirred with ice-water of pH 1.8. The organic phase is then washed with cold sodium carbonate solution and with 15% sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is ethyl 2-bromo-6-trifluoromethyinicotinate in the form of an oil; 1H-NMR (CDCl3): 8.20, d, CH, 7.72 d, CH, 4.46, q, CH2, 1.42 ppm, t, CH3 of melting point 164-166° C.

[0187] 1.0 g (3.4 mmol) of this product, dissolved in a small amount of acetonitrile, is heated for 45 minutes to a temperature of 70° C. together with 0.26 g of sodium methanethiolate (3.4 mmol) in the presence of a catalytic amount of 15-crown-5 ether. The solution, which is cooled to room temperature, is then treated with 0.22 g (5.5 mmol) of sodium hydroxide and 5 ml of water, and stirring is continued for 3 hours. The neutral components are subsequently removed with a small amount of diethyl ether, and the aqueous phase is brought to pH 2.5 and extracted twice using ethyl acetate. This gives 2-methylthio-6-trifluoromethyinicotinic acid as crystalline product; 1H-NMR (CDCl3): 8.46, d, CH, 7.43, d, CH, 2.58 ppm, s, SCH3.

Example H14

2-Methanesulfonylamino-6-trifluoromethyinicotinic Acid (Compound A1203)

[0188] 0.52 g of methanesulfonamide is introduced into a tetrahydrofuran suspension of 0.24 g of 55% sodium hydride in oil. After the evolution of hydrogen has ceased, 1.5 9 (5 mmol) of ethyl 2-bromo-6-trifluoromethyinicotinate, 0.3 g (5.2 mmol) of potassium fluoride and a catalytic amount of crown ether and 5 ml of N-methylpyrrolidone are added and the mixture is heated at the boil for 18 hours. The reaction mixture is then partitioned between ethyl acetate and water and freed from organic neutral constituents. The aqueous phase is brought to pH 2.9, extracted 3 times with fresh ethyl acetate, dried and concentrated. A crystalline product, ethyl 2-methanesulfonylamino-6-trifluoromethyinicotinate, is obtained from etherihexane; 1H-NMR (CDCl3): 10.48, s, NH, 8.49, d, CH, 7.38, d, CH, 4.45, q, CH2, 3.51, S, SO2CH3, 1.42 ppm, t, CH3.

[0189] 0.43 g (1.4 mmol) of the above product is hydrolysed at room temperature using a 1:1 solution of 0.22 g (3.9 mmol) of potassium hydroxide in dioxane/water. After the solution, which has been acidified to pH 2.5, has been extracted with ethyl acetate, 2-methanesulfonylamino-6-trifluoromethylnicotinic acid is obtained as crystallisate; 1H-NMR (d6-DMSO): 8.62, d, CH, 7.72, d, CH, 3.52 ppm, S, SO2CH3.

Example H15

(3-Methoxycarbonyl-6-trifluoromethylpyridin-2-ylmethyl)phenylphosphonium Bromide

[0190] 50 g (0.23 mol) of methyl 2-methyl-6-trifluoromethyinicotinate and 49 g (0.28 mol) of N-bromosuccinimide are heated for 90 minutes at 50° C. in 500 ml of carbon tetrachloride in the presence of a catalytic amount of α,α-azaisobutyronitrile with illumination by a 150 watt lamp. Precipitated succinimide is filtered off, and the product methyl 2-bromomethyl-6-trifluoromethyinicotinate is then isolated as main component by means of column chromatography (mobile phase ethyl acetate/hexane 1:15), 1H-NMR (CDCl3): 4.01, s, 3H; 5.03, s, 2H; 7.72, d (J 8.2 Hz), 1H; 8.43 ppm, d, (J 8.2 Hz), 1H. 25.6 g (35 mmol) of the above product are taken up in toluene and treated with 10.6 g (40 mmol) of triphenylphosphine. After the mixture has been heated for 2 hours at boiling point, pure (3-methoxycarbonyl-6-trifluoromethylpyridine-2-ylmethyl)triphenylphosphonium bromide of melting point 215-217° C. crystallizes out upon cooling.

Example H16

2-Vinyl-6-trifluoromethyinicotinic Acid (Compound A21) and 2-(2.2-dichloro-cyclopropyl)-6-trifluoromethylnicotinic Acid (Compound A1092)

[0191] 5.7 g (10 mmol) of (3-methoxycarbonyl-6-trifluoromethylpyridine-2-ylmethyl)triphenyl-phosphonium bromide are dissolved at room temperature in a 2-phase system of 25 ml of chloroform and 2.1 g (20 mmol) of sodium carbonate and reacted, in 10 ml of water, with a 35% aqueous solution of 1.7 g (20 mmol) of formaldehyde. After 1.5 hours, the organic phase is separated off and filtered through silica gel. Methyl 2-vinyl-6-trifluoromethylnicotinate is obtained as an oil, 1H-NMR (CDCl3): 8.31, d, CH, 7.10, dd, CH, 7.09, d, CH, 6.68, dd, CH, 5.68, dd, CH, 3.97 ppm, s, OCH3.

[0192] 0.97 g (4.1 mmol) of this product is again taken up in chloroform and reacted with 6 ml of 50% sodium hydroxide solution with vigorous stirring in the presence of 90 mg of benzyltrimethylammonium bromide. After 20 hours, the organic phase is separated off, concentrated and purified by HPLC (mobile phase: ethyl acetate/hexane 1:4). This gives pure methyl 2-(2,2-dichlorocyclopropyl)-6-trifluoromethyinicotinate, 1H-NMR (CDCl3): 8.50, d, CH, 7.70, d, CH, 4.08, sl OCH3, 3.68, dd, CH, 2.64, dd, CH, 2.05 ppm, dd, CH.

[0193] Hydrolysis of the above esters gives, accordingly, the 2-vinyl-6-trifluoromethyinicotinic acid, 1H-NMR (CDCl3): 8.40, d, CH, 7.22, dd, CH, 7.09, d, CH, 6.68, dd, CH, 5.58 ppm, dd, CH, and 2-(2,2-dichlorocyclopropyl)-6-trifluoromethyinicotinic acid, 1H-NMR (CDCl3): 8.64, d, CH, 7.23, d, CH, 3.78, dd, CH, 2,67, dd, CH, 2,08 ppm, dd, CH.

Example H17

2-Prona-1,2-dienyl-6-trifluoromethyinicotinic Acid (A1096) and 2-(3-chloropronenyl)-6-trifluoromethylnicotinic Acid (Compound A1095).

[0194] 6.7 g (11 mmol) of ((3-methoxycarbonyl-6-trifluoromethylpyridin-2-yl)methyl)triphenyl-phosphonium bromide are reacted with 2 ml of 45% aqueous chloroacetaldehyde solution (14 mmol) and 1.5 g (14 mmol) of sodium carbonate with vigorous stirring in a 2-phase system of 20 ml of chloroform and 7 ml of water. After 2 hours, the organic solution is separated off and washed with half-saturated sodium chloride solution. The product is separated on silica gel (mobile phase ethyl acetate/hexane 1:4). As the 1 st fraction, methyl 2-propa-1,2-dienyl-6-trifluoromethylnicotinate, 1H-NMR (CDCl3): 7.62, m, CH, 7.55, d, CH, 7.32, d, CH, 7.04, d, CH, 7.02, m, CH, 3.98 ppm, s, OCH3, is isolated, and methyl 2-(3-chloropropenyl)-6-trifluoromethyinicotinate, 1H-NMR (CDCl3): 8.85, d, CH, 7.65, dd, 7.58, d, CH, CH, 7.28, dd, CH, 4.32, d, CH2Cl, 3.98 ppm, s, OCH3 is isolated as the 2nd fraction.

[0195] Hydrolysis of the above esters gives 2-propa-1,2-dienyl-6-trifluoromethyinicotinic acid, m.p. 194-196° C., and 2-(3-chloropropenyl)-6-trifluoromethyinicotinic acid, m.p. 137-138° C.

Example H18

2-Chloro-4-methyl-6-trifluoromethylnicotinic Acid (Compound A1205)

[0196] In a pressurized vessel, 7.5 g (0.03 mol) of ((3-ethoxycarbonyl)-4-methyl-6-trifluoromethyl)-pyrid-2-one is heated for 3 hours at a temperature of 170° C. in the presence of 5.8 ml of phenyl dichlorophosphate. When cold, the reaction solution is filtered directly over a short silica gel column (mobile phase: ethyl acetate/hexane 1:9), and the 2-chloro-4-methyl-6-trifluoromethylpyridin-3-ylethyl ester is obtained as oily product. The latter is hydrolysed in the presence of aqueous potassium hydroxide solution in dioxane at a temperature of 40° C. After acidification to pH 2.7, extraction with ethyl acetate gives 2-chloro-4-methyl-6-trifluoromethyinicotinic acid as crystalline product: 1H NMR (CDCl3): 9.55, b, OH, 7.55, s, 1H; 3.80, s, CH3, 2.56 ppm, s, CH3.

Example H19

4-Methyl-6-trifluoromethylnicotinic Acid (Compound A531)

[0197] To a suspension of 0.55 g of 10% Pd/C in 20 ml of methanol there are added 3.0 g (16.8 mmol) of the 2-chloro-4-methyl-6-trifluoromethylpyridin-3-ylethyl ester and, in 2 portions, a total of 5 g of ammonium formate, and the mixture is stirred for 24 hours at room temperature. The reaction mixture is then filtered through Celite and partitioned between ethyl acetate and sodium chloride solution. Chromatographic purification (mobile phase 1:9) gives the 4-methyl-6-trifluoromethylpyridin-3-ylethyl ester in the form of an oil: hydrolysis in accordance with the above processes gives 4-methyl-6-trifluoromethyinicotinic acid: 1H NMR (CDCl3): 9.32, s, 1H, 7.62, s, 1H, 2.79 ppm, s, CH3.

Examole H20

5-Methyl-5-methylsulfanvibicyclor4.1.0]heptane-2,4-dione (compound H-D113):

[0198] A 1-molar solution of 16.7 g (0.1 mol) of lithium bistrimethylsilylamide in tetrahydrofuran is added at a temperature of 0° C. to a solution of 13.4 g (0.1 mol) of methyl 2-methylmercaptopropionate in 30 ml of tetrahydrofuran. After the mixture has been stirred for 1 hour, 11.8 g (0.1 mol) of 5-chloropent-3-en-2-one are added dropwise in the course of 20 minutes in such a way that the temperature can be maintained at 0° C. After the mixture has been stirred for a further 30 minutes, ice-water is added, and the mixture is acidified with hydrochloric acid and extracted with diethyl acetate. The crude product is chromatographed with ethyl acetatelhexane 15/85. This gives methyl 2-(2-acetylcyclopropyl)-2-methylsulfanylpropionate, 1H-NMR (CDCl3): 3.74, s, OCH3, 2.19 and 2.14, 2s, SCH3, 2.12. and 2.00, 2s, CH3, 2.2-1.9, 1H, 1.3, s, CH3, 1.3 to 1.0 ppm, 2H, as a 3:7 isomer mixture.

[0199] 2.45 g (11 mmol) of the above product, which is enriched in the more polar isomer, is heated with 4.5 g (25 mmol) of 30% sodium ethoxide solution in a mixture of toluene/dimethylformamide 19:1 for 90 minutes at 115° C. The mixture is then taken up in ethyl acetate and washed with dilute hydrochloric acid at pH 3. The residue which has been isolated is purified on silica gel (mobile phase ethyl acetate/hexane 1:2). This gives the isomer I of 5-methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione, 1H-NMR (CDCl3): 3.48, d, CH, 3.00 d, CH, 2.21, m, CH, 1.94, m, CH, 1.86, s, CH3, 1.57, s, CH3, 1.44, m, CH, 1.04 ppm, m, CH.

[0200] The isomer 11 of 5-methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione, 1H-NMR (CDCl3): 3.78, d, CH, 3.14 d, CH, 2.22, m, CH, 1.93, m, CH, 2.08, s, CH3, 1.58, s, CH3, 1.6-1.4 ppm, 2H, is obtained from the product which is enriched in apolar isomers.

Example H21

4-Methylcyclohept-4-ene-1,3-dione (compound H-F5)

[0201] 1.0 g (5.4 mmol) of the 5-methyl-5-methylsulfanylbicyclo[4.1.0)heptane-2,4-dione isomers 11 is hydrogenated for 90 minutes under atmospheric pressure in 15 ml of methanol in the presence of 5 9 Raney nickel. The mixture is concentrated and purified over silica gel (mobile phase ethyl acetate/hexane 1:1), and 4-methylcyclohept-4-ene-1,3-dione, 1H-NMR (CDCl3): 6.84, m, CH, 3.94, s, CH2, 2.77, m, CH2, 2,59, m, CH2, 1.88 ppm, s, CH3, is obtained as an oil.

Example H22

2-Oxaspiro[4.5]decane-1.6,8-trione (compound H-E16)

[0202] A suspension of sodium hydride (55% in oil, 27.5 mmol) in 70 ml of anhydrous tetrahydrofuran is cooled to a temperature of −20° C., and a solution of 2-acylbutyrolactone (2.69 ml, 25 mmol) in 5 ml of tetrahydrofuran is subsequently added dropwise. After the reaction mixture has been stirred for 1 hour at this temperature, it is treated dropwise with a solution of methyl acrylate (4.5 ml, 50 mmol) in tetrahydrofuran at a temperature of −20° C. The reaction mixture is subsequently allowed to warm to room temperature and is stirred for 8 hours. The mixture is then poured into ice-water and acidified with 2 N hydrochloric acid to pH 1. After extraction with ethyl acetate, drying over sodium sulfate and concentration in vacuo, the product is purified by flash chromatography (eluent: ethyl acetate/acetic acid 1:1). This gives 2-oxaspiro[4.5]decane-1,6,8-trione in the form of a white powder of melting point 145-148° C.

Example H23

Spiro[2.5]octane-4,6-dione (compound H-C1)

[0203] 3.4 g of sodium hydride (55% suspension in oil, 78.0 mmol) were introduced into 1 l of tert-butanol and the mixture was stirred for a few minutes at room temperature. Then, 2-acylbutyrolactone (100 g, 0.78 mol) is added and the reaction mixture is treated with methyl acrylate (67.2 g, 0.78 mmol) over a period of 3.5 hours at a temperature of approx. 30° C. The reaction mixture is taken up in diethyl ether and washed in succession with 75 ml of saturated NaH2PO4 solution, water and saturated sodium chloride solution, dried over sodium sulfate and concentrated. This gives 162 g of methyl 3-(3-acetyl-2-oxotetrahydrofuran-3-yl)propionate as colourless oil, which can be reacted further without purification.

[0204] 2.0 g (9.3 mmol) of the above product and 2.1 g of sodium iodide (14.0 mmol) are dissolved in 10 ml of 1 ,3-dimethyl-2-imidazolidinone and the solution is heated for 3 hours at 210° C. After cooling, the reaction mixture is poured into dilute aqueous saturated NaH2PO4 solution and extracted with diethyl ether, dried over sodium sulfate and concentrated. This gives methyl 3-(1-acetylcyclopropyl)propionate as a colourless oil.

[0205] 74.5 g of methyl 3-(1-acetylcyclopropyl)propionate (0.32 mol) are dissolved in 1 l of tetrahydrofuran and the solution is treated portionwise with 14.3 g of sodium hydride (55% suspension in oil, 0.32 mol) at room temperature. After 1 hour, the reaction mixture is diluted with 200 ml of dimethylformamide and warmed to 70° C. After 8 hours, tetrahydrofuran is removed in vacuo, and the residue is poured into 2 N hydrochloric acid and extracted with diethyl ether The organic phase is dried over sodium sulfate and concentrated, and column chromatography over silica gel (methylene chloride:ethanol 9:1 as eluent) gives spiro[2.5]octane-4,6-dione in the form of white crystals of melting point 116-118° C.

Example H24

2-(4,6-Dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethyinicotinic Acid (Compound A1088)

[0206] 2.0 g (7.89 mmol) of methyl 2-chloromethyl-6-trifluoromethyinicotinate (prepared analogously to Heterocycles, 46, 129 (1997) by heating methyl 4-chloro-3-oxobutyrate and 4-amino-1,1 ,1-trifluorobut-3-en-2-one in toluene in the presence of trifluoroacetic acid) are introduced into 30 ml of acetonitrile and 1.63 9 (11.83 mmol) of K2CO3 and reacted with 1.49 g (8.67 mmol) of 4,6-dimethoxypyrimidin-2-thiol at room temperature. After 4 hours, the mixture is poured into ethyl acetate/water, the ethyl acetate phase is removed, and the aqueous phase is reextracted with ethyl acetate. The combined ethyl acetate phases are dried over sodium sulfate, concentrated and purified by recrystallization from ethyl acetateihexane. This gives methyl 2-(4,6-dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethylnicotinate in the form of white crystals of melting point 123-124° C.

[0207] Hydrolysis of the above esters (analogously to Example H1) gives, accordingly, 2-(4,6-dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethylnicotinic acid in the form of white crystals of melting point 157-158° C. 1H-NMR (CDCl3): 3.96, s, 6H; 3.99,s, 3H; 5.03, s, 2H; 5.72, s, 1H; 7.66,d (J, 8.1 Hz),1H; 8.40 ppm, d (J, 8.1 Hz),1H.

Example H25

2-Cyanomethyl-6-trifluoromethylnicotinic acid (compound A1103)

[0208] 2.0 g (7.89 mmol) of methyl 2-chloromethyl-6-trifluoromethylnicotinate and 565 mg (8.67 mmol) of potassium cyanide are reacted in 20 ml of acetonitrile/water mixture (1:1) in the presence of 270 mg of tetrabutylammonium hydrogen sulfate. After the reaction has ended, the mixture is poured into water and extracted with ethyl acetate. After the ethyl acetate phase has been dried over sodium sulfate and concentrated, the crude product is purified by means of HPLC (ethyl acetate: hexane as eluent). This gives 610 mg (32% of theory) of methyl 2-cyanomethyl-6-trifluoromethyinicotinate in the form of an oil. 1H-NMR (CDCl3): 3.96, s, 3H; 4.38, s, 2H; 7.72,d (J, 8.1 Hz),1H; 8.48 ppm, d (J, 8.1 Hz),1H.

[0209] Hydrolysis analogous to the methods already mentioned above yields 2-cyanomethyl-6-trifluoromethyinicotinic acid in the form of yellow crystals of melting point 152-153° C. 1H-NMR (CDCl3): 4.18, s, 2H; 7.72,d (J, 8.1 Hz),1H; 8.52 ppm, d (J, 8.1 Hz), 1H.

Example H26

3-(6-Difluoromethyl-2-methylpyridine-3-carbonyl)-2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate (compound A124-B34)

[0210] 200 mg (0.516 mmol) of methyl 3-[6-(chlorodifluoromethyl)-2-methylpyridine-3-carbony1]-2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate (compound A94-B34) is heated for 3 hours at a temperature of 120° C. in 8 ml of toluene in the presence of 0.18 ml (0.62 mmol) tris(trimethylsilyl)silane. The viscous residue which remains is chromatographed on silica gel. The pale yellow viscous oil which is obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 by volume) is dissolved in dichloromethane and washed in succession with aqueous hydrochloric acid and water. Evaporation of the organic solution which has been dried with Na2SO4 yields 140 mg (73%) of pure methyl 3-(6-difluoromethyl-2-methylpyridine-3-carbonyl)-2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate in the form of a pale yellow oil. 1H-NMR (CDCl3): 1.28, s, 3H; 1.79-1.97, m, 1H; 2.39-2.46, m,1H; 2.43, s, 3H; 2.69, dt (J, 19.2 and 4.8 Hz),1H; 2.82-2.92, m,1H; 3.67, s, 3H; 6.55, t, (J, 55.5 Hz),1H; 7.43, d (J, 7.8 Hz), 1H; 7.49, d (J, 7.8 Hz), 1H; 17.20 ppm, br s, 1H.

Example H27

3-Hydroxy-2-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (Compound A1210-B1)

[0211] 16.1 g (0.054 mol) of 3-hydroxy-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (Example A2-Bi) and 10.2 9 (0.11 mol) of urealhydrogen peroxide complex are dissolved in 150 ml of methylene chloride, and 22.1 ml (0.162 mol) of trifluoroacetic anhydride are subsequently added dropwise at a temperature of 25° C. After the reaction mixture has been stirred for 14 hours at a temperature of 25° C., it is poured into ethyl acetate and water, and the organic phase is washed twice with water, dried with sodium sulfate and concentrated. The residue is chromatographed on silica gel (eluent: ethyl acetate/methanol 9/1). This gives 2.4 g (14%) of the desired product in the form of white crystals (m.p. 117-119° C.). 1H-NMR (d6-DMSO): 1.98, m, 2H; 2.30, s, 3H; 2.60, t (J, 7.25 Hz), 4H: 7.32, d (J, 9.8 Hz), 1H; 7.92 ppm, d (J, 9.8 Hz), 1H.

Example H28

2-(2-Methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcyclohex-2-enone (Compound A2-B1102)

[0212] 4.0 g (0.0134 mol) of 3-hydroxy-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (compound A2-B1) are suspended in 25 ml of oxalyl chloride, and 0.1 ml of dimethylformamide is subsequently added dropwise. After the vigorous evolution of gas has ceased, the mixture is held for 1.5 hours at a bath temperature of 45° C. and subsequently concentrated, and the residue (3-chloro-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-cyclohex-2-enone) is dissolved in 60 ml of methylene chloride. Triethylamine (3.7 ml, 0.0268 mol), dimethylaminopyridine (160 mg, 1.34 mmol) and 1.5 ml (0.0147 mol) of thiophenol are added at a temperature of 0-5° C. After 20 hours at a temperature of 22° C., the reaction mixture is concentrated and purified on silica gel (hexane/ethyl acetate 5:1). Trituration in hexane gives pure 2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcyclohex-2-enone in the form of white crystals of melting point 124-125° C. 1H-NMR (CDCl3): 1.99, m, 2H; 2.41, m 4H; 2.80, s, 3H; 2.60: 7.40-7.60, m, 6H; 7.80 ppm, d (J, 8.2 Hz),1H.

Example H29

3-Benzenesulfonyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (compound A2-B1 104):

[0213] 0.8 g (0.00204 mol) of the 2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcyclohex-2-enone obtained above is dissolved in 30 ml of methylene chloride, and 1.39 ml of peracetic acid (39% in acetic acid, 0.00816 mol) are subsequently added dropwise at a temperature of 25° C. After 4 hours at 250C, the reaction mixture is poured into ethyl acetate and water, the organic phase is washed with water, dried with sodium sulfate and concentrated, and the residue is triturated with a small amount of hexane and ethyl acetate. Filtration gives 0.72 g (84% of theory) of 3-benzenesulfonyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone in the form of white crystals of melting point 165-167° C.1H-NMR (CDCl3): 2.30, m, 2H; 2.55, t (J, 7 Hz), 2H; 2.71, m, 2H; 3.05, s, 3H; : 7.40-7.80, m, 4H; 7.80-8.05 ppm, m, 3H.

Example H30

6-Difluoromethyl-2-methvinicotinic Acid (Compound A124)

[0214] 6.19 (0.026 mol) of methyl 6-(chlorodifluoromethyl)-2-methylnicotinate (prepared analogously to Heterocycles, 46, 129 (1997) by heating methyl 3-oxobutyrate and 4-amino-1-chloro-1,1-difluorobut-3-en-2-one in toluene in the presence of trifluoroacetic acid) is heated at a temperature of 120° C. in the presence of 430 mg (0.26 mol) of tris(trimethylsilyl)silane in 150 ml of toluene. After 1.5 hours, the reaction mixture is concentrated and purified on silica gel (hexane/ethyl acetate 13:1). This gives 3.8 g (73% of theory) of methyl 6-difluoromethyl-2-methyinicotinate as colourless oil.

[0215] Hydrolysis of the above esters (analogously to Example H1) gives, accordingly, 6-difluoromethyl-2-methyinicotinic acid in the form of white crystals of melting point 135-136° C. 1H-NMR (CDCl3): 2.68, s, 3H; 6.583, t (J, 55.2 Hz), 1H;: 7.54, d (J, 8.1 Hz), 1H; 7.54 ppm, d (J, 8.1 Hz), 1H.

Example H31

6-(Chlorodifluoromethyl)-2-methvinicotinic acid (compound A-94):

[0216] 5.0 g (18.62 mmol) of methyl 2-methyl-6-trichloromethyinicotinate (prepared analogously to Heterocycles, 46, 129 (1997)) are cooled to a temperature of −40° C. in a pressurized container, and 35 g (1.75 mol) of distilled hydrofluoric acid are subsequently passed in at this temperature. The mixture is heated for 10 hours at 200° C. (pressure approx. 55 bar). After cooling, the pressure is released using a gas-washing system, HF is removed by suction, and the reaction mixture is poured into ethyl acetatefice. The ethyl acetate phase is separated off, and the aqueous phase is reextracted using ethyl acetate. The combined ethyl acetate phases are washed with water, dried over sodium sulfate and concentrated, and the residue is triturated with a small amount of hexane and ethyl acetate. Filtration gives 2.2 g (53% of theory) of 6-chlorodifluoromethyl-2-methyinicotinic acid as pale green crystals of melting point 134-135° C.

[0217] 1H-NMR (CDCl3): 2.987, s, 3H; 7.64,d (J, 8.1 Hz), 1H; 8.513 ppm, d (J, 8.1 Hz), 1H.

Example H32

2-f2-(4,6-Dimethoxypyrimidine-2-sulfonylmethyl)-6-trifluoromethylpyridine-3-carbonyl]-3-hydroxycyclohex-2-enone (Compound A1090-Bt )

[0218] 100 mg of 2-[2-(4,6-dimethoxypyrimidin-2-yisulfanylmethyl)-6-trifluoromethylpyridine-3-carbonyl]-3-hydroxycyclohex-2-enone (compound A1088-B1) are dissolved in methylene chloride, and 0.3 ml of peracetic acid (39% in acetic acid) is subsequently added dropwise at a temperature of 25° C. After 15 hours at 25° C., the reaction mixture is poured into ethyl acetate and water, and the organic phase is washed with water, dried with sodium sulfate and concentrated. This gives 95 mg of 2-[2-(4,6-dimethoxypyrimidine-2-sulfonylmethyl)-6-trifluoromethylpyridine-3-carbonyl]-3-hydroxycyclohex-2-enone in the form of a resin. 1H-NMR (CDCl3): 3.79, s, 6H; 3.91, s, 3H; 4.99, s, 2H; 6.09, s, 1H; 7.52, d (J, 9 Hz),1H; 7.68 ppm, d (J, 9 Hz),1H.

[0219] In the tables which follow, Ph is the phenyl group and CC an ethyne group. 1

TABLE 1
Compounds of the formula XVId:
41embedded image
Comp.
No.R2R3R4R5p
A1HHHCF30
A2CH3HHCF30
A3CH3CH2HHCF30
A4(CH3)2CHHHCF30
A5(CH3)3CHHCF30
A6cyclopropylHHCF30
A7CH3(CH2)2HHCF30
A8CH3OCH2HHCF30
A9CH3O(CH2)2HHCF30
A10PhHHCF30
A11PhOHHCF30
A12PhSHHCF30
A13PhSOHHCF30
A14PhSO2HHCF30
A15CH3SHHCF30
A16CH3SOHHCF30
A17CF3HHCF30
A18F2CHHHCF30
A19HCCHHCF30
A20CH3CCHHCF30
A21CH2═CHHHCF30
A22CH2═CHCH2HHCF30
A23CH3SO2N(CH3)HHCF30
A24(CH3)2NHHCF30
A25(CH3)2NSO2HHCF30
A26ClCH2HHCF30
A27CH3SCH2HHCF30
A28CH3SOCH2HHCF30
A29CH3SO2CH2HHCF30
A30[1.2.4]-triazol-1-ylmethylHHCF30
A31CH3CF3HCH30
A32CH3CH3HCF30
A33HHHCF3CF20
A34CH3HHCF3CF20
A35CH3CH2HHCF3CF20
A36cyclopropylHHCF3CF20
A37(CH3)3CHHCF3CF20
A38(CH3)2CHHHCF3CF20
A39CH3(CH2)2HHCF3CF20
A40CH3OCH2HHCF3CF20
A41CH3O(CH2)2HHCF3CF20
A42PhHHCF3CF20
A43PhOHHCF3CF20
A44PhSHHCF3CF20
A45PhSOHHCF3CF20
A46PhSO2HHCF3CF20
A47CH3SHHCF3CF20
A48CH3SOHHCF3CF20
A49CF3HHCF3CF20
A50F2CHHHCF3CF20
A51HCCHHCF3CF20
A52CH3CCHHCF3CF20
A53CH2═CHHHCF3CF20
A54CH2═CHCH2HHCF3CF20
A55CH3SO2N(CH3)HHCF3CF20
A56(CH3)2NHHCF3CF20
A57(CH3)2NSO2HHCF3CF20
A58ClCH2HHCF3CF20
A59CH3SCH2HHCF3CF20
A60CH3SOCH2HHCF3CF20
A61CH3SO2CH2HHCF3CF20
A62[1.2.4]-triazol-1-ylmethylHHCF3CF20
A63HHHCF3CF2CF20
A64CH3HHCF3CF2CF20
A65CH3CH2HHCF3CF2CF20
A66cyclopropylHHCF3CF2CF20
A67(CH3)3CHHCF3CF2CF20
A68(CH3)2CHHHCF3CF2CF20
A69CH3(CH2)2HHCF3CF2CF20
A70CH3OCH2HHCF3CF2CF20
A71CH3O(CH2)2HHCF3CF2CF20
A72PhHHCF3CF2CF20
A73PhOHHCF3CF2CF20
A74PhSHHCF3CF2CF20
A75PhSOHHCF3CF2CF20
A76PhSO2HHCF3CF2CF20
A77CH3SHHCF3CF2CF20
A78CH3SOHHCF3CF2CF20
A79CF3HHCF3CF2CF20
A80F2CHHHCF3CF2CF20
A81HCCHHCF3CF2CF20
A82CH3OOHHCF3CF2CF20
A83CH2═CHHHCF3CF2CF20
A84CH2═CHCH2HHCF3CF2CF20
A85CH3SO2N(CH3)HHCF3CF2CF20
A86(CH3)2NHHCF3CF2CF20
A87(CH3)2NSO2HHCF3CF2CF20
A88ClCH2HHCF3CF2CF20
A89CH3SCH2HHCF3CF2CF20
A90CH3SOCH2HHCF3CF2CF20
A91CH3SO2CH2HHCF3CF2CF20
A92[1.2.4]-triazol-1-ylmethylHHCF3CF2CF20
A93HHHCF2Cl0
A94CH3HHCF2Cl0
A95CH3CH2HHCF2Cl0
A96cyclopropylHHCF2Cl0
A97(CH3)3CHHCF2Cl0
A98(CH3)2CHHHCF2Cl0
A99CH3(CH2)2HHCF2Cl0
A100CH3OCH2HHCF2Cl0
A101CH3O(CH2)2HHCF2Cl0
A102PhHHCF2Cl0
A103PhOHHCF2Cl0
A104PhSHHCF2Cl0
A105PhSOHHCF2Cl0
A106PhSO2HHCF2Cl0
A107CH3SHHCF2Cl0
A108CH3SOHHCF2Cl0
A109CF3HHCF2Cl0
A110F2CHHHCF2Cl0
A111HCCHHCF2Cl0
A112CH3CCHHCF2Cl0
A113CH2═CHHHCF2Cl0
A114CH2═CHCH2HHCF2Cl0
A115CH3SO2N(CH3)HHCF2Cl0
A116(CH3)2NHHCF2Cl0
A117(CH3)2NSO2HHCF2Cl0
A118ClCH2HHCF2Cl0
A119CH3SCH2HHCF2Cl0
A120CH3SOCH2HHCF2Cl0
A121CH3SO2CH2HHCF2Cl0
A122[1.2.4]-triazol-t-ylmethylHHCF2Cl0
A123HHHCHF20
A124CH3HHCHF20
A125CH3CH2HHCHF2Q
A126cyclopropylHHCHF20
A127(CH3)3CHHCHF20
A128(CH3)2CHHHCHF20
A129CH3(CH2)2HHCHF20
A130CH3OCH2HHCHF20
A131CH3O(CH2)2HHCHF20
A132PhHHCHF20
A133PhOHHCHF20
A134PhSHHCHF20
A135PhSOHHCHF20
A136PhSO2HHCHF20
A137CH3SHHCHF20
A138CH3SOHHCHF20
A139CF3HHCHF20
A140F2CHHHCHF20
A141HCCHHCHF20
A142CH3CCHHCHF20
A143CH2═CHHHCHF20
A144CH2═CHCH2HHCHF20
A145CH3SO2N(CH3)HHCHF20
A146(CH3)2NHHCHF20
A147(CH3)2NSO2HHCHF20
A148ClCH2HHCHF20
A149CH3SCH2HHCHF20
A150CH3SOCH2HHCHF20
A151CH3SO2CH2HHCHF20
A152[1.2.4]-triazol-1-ylmethylHHCHF20
A153HHHCCl30
A154CH3HHCCl30
A155CH3CH2HHCCl30
A156cyolopropylHHCCl30
A157(CH3)3CHHCCl30
A158(CH3)2CHHHCCl30
A159CH3(CH2)2HHCCl30
A160CH3OCH2HHCCl30
A161CH3O(CH2)2HHCCl30
A162PhHHCCl30
A163PhOHHCCl30
A164PhSHHCCl30
A165PhSOHHCCl30
A166PhSO2HHCCl30
A167CH3SHHCCl30
A168CH3SOHHCCl30
A169CF3HHCCl30
A170F2CHHHCCl30
A171HCCHHCCl30
A172CH3CCHHCCl30
A173CH2═CHHHCCl30
A174CH2═CHCH2HHCCl3 0
A175CH3SO2N(CH3)HHCCl3 0
A176(CH3)2NHHCCl3 0
A177(CH3)2NSO2HHCCl3 0
A178ClCH2HHCCl3 0
A179CH3SCH2HHCCl3 0
A180CH3SOCH2HHCCl3 0
A181CH3SO2CH2HHCCl3 0
A182[1.2.4]-triazol-l-ylmethylHHCCl3 0
A183HHCH3CF30
A184CH3HCH3CF30
A185CH3CH2HCH3CF30
A186cyclopropylHCH3CF30
A187(CH3)3CHCH3CF30
A188(CH3)2CHHCH3CF30
A189CH3(CH2)2HCH3CF30
A190CH3OCH2HCH3CF30
A191CH3O(CH2)2HCH3CF30
A192PhHCH3CF30
A193PhOHCH3CF30
A194PhSHCH3CF30
A195PhSOHCH3CF30
A196PhSO2HCH3CF30
A197CH3SHCH3CF30
A198CH3SOHCH3CF30
A199CF3HCH3CF30
A200F2CHHCH3CF30
A201HCCHCH3CF30
A202CH3CCHCH3CF30
A203CH2═CHHCH3CF30
A204CH2═CHCH2HCH3CF30
A205CH3SO2N(CH3)HCH3CF30
A206(CH3)2NHCH3CF30
A207(CH3)2NSO2HCH3CF30
A208ClCH2HCH3CF30
A209CH3SCH2HCH3CF30
A210CH3SOCH2HCH3CF30
A211CH3SO2CH2HCH3CF30
A212HHCH3CF3CF20
A213CH3HCH3CF3CF20
A214CH3CH2HCH3CF3CF20
A215cyclopropylHCH3CF3CF20
A216(CH3)3CHCH3CF3CF20
A217(CH3)2CHHCH3CF3CF20
A218CH3(CH2)2HCH3CF3CF20
A219CH3OCH2HCH3CF3CF20
A220CH3O(CH2)2HCH3CF3CF20
A221PhHCH3CF3CF20
A222PhOHCH3CF3CF20
A223PhSHCH3CF3CF20
A224PhSOHCH3CF3CF20
A225PhSO2HCH3CF3CF20
A226CH3SHCH3CF3CF20
A227CH3SOHCH3CF3CF20
A228CF3HCH3CF3CF20
A229F2CHHCH3CF3CF20
A230HCCHCH3CF3CF20
A231CH3CCHCH3CF3CF20
A232CH2═CHHCH3CF3CF20
A233CH2═CHCH2HCH3CF3CF20
A234CH3SO2N(CH3)HCH3CF3CF20
A235(CH3)2NHCH3CF3CF20
A236(CH3)2NSO2HCH3CF3CF20
A237ClCH2HCH3CF3CF20
A238CH3SCH2HCH3CF3CF20
A239CH3SOCH2HCH3CF3CF20
A240CH3SO2CH2HCH3CF3CF20
A241HHCH3CF3CF2CF20
A242CH3HCH3CF3CF2CF20
A243CH3CH2HCH3CF3CF2CF20
A244cyclopropylHCH3CF3CF2CF20
A245(CH3)3CHCH3CF3CF2CF20
A246(CH3)2CHHCH3CF3CF2CF20
A247CH3(CH2)2HCH3CF3CF2CF20
A248CH3OCH2HCH3CF3CF2CF20
A249CH3(CH2)2HCH3CF3CF2CF20
A250PhHCH3CF3CF2CF20
A251PhOHCH3CF3CF2CF20
A252PhSHCH3CF3CF2CF20
A253PhSOHCH3CF3CF2CF20
A254PhSO2HCH3CF3CF2CF20
A255CH3SHCH3CF3CF2CF20
A256CH3SOHCH3CF3CF2CF20
A257CF3HCH3CF3CF2CF20
A258F2CHHCH3CF3CF2CF20
A259HCCHCH3CF3CF2CF20
P260CH3CCHCH3CF3CF2CF20
A261CH2═CHHCH3CF3CF2CF20
A262CH2═CHCH2HCH3CF3CF2CF20
A263CH3SO2N(CH3)HCH3CF3CF2CF20
A264(CH3)2NHCH3CF3CF2CF20
A265(CH3)2NSO2HCH3CF3CF2CF20
A266ClCH2HCH3CF3CF2CF20
A267CH3SCH2HCH3CF3CF2CF20
A268CH3SOCH2HCH3CF3CF2CF20
A269CH3SO2CH2HCH3CF3CF2CF20
A270HHCH3CF2Cl0
A271CH3HCH3CF2Cl0
A272CH3CH2HCH3CF2Cl0
A273cyclopropylHCH3CF2Cl0
A274(CH3)3CHCH3CF2Cl0
A275(CH3)2CHHCH3CF2Cl0
A276CH3(CH2)2HCH3CF2Cl0
A277CH3OCH2HCH3CF2Cl0
A278CH3O(CH2)2HCH3CF2Cl0
A279PhHCH3CF2Cl0
A280PhOHCH3CF2Cl0
A281PhSHCH3CF2Cl0
A282PhSOHCH3CF2Cl0
A283PhSO2HCH3CF2Cl0
A284CH3SHCH3CF2Cl0
A285CH3SOHCH3CF2Cl0
A286CF3HCH3CF2Cl0
A287F2CHHCH3CF2Cl0
A288HCCHCH3CF2Cl0
A289CH3CCHCH3CF2Cl0
A290CH2═CHHCH3CF2Cl0
A291CH250 CHCH2HCH3CF2Cl0
A292CH3SO2N(CH3)HCH3CF2Cl0
A293(CH3)2NHCH3CF2Cl0
A294(CH3)2NSO2HCH3CF2Cl0
A295ClCH2HCH3CF2Cl0
A296CH3SCH2HCH3CF2Cl0
A297CH3SOCH2HCH3CF2Cl0
A298CH3SO2CH2HCH3CF2Cl0
A299HHCH3CHF20
A300CH3HCH3CHF20
A301CH3CH2HCH3CHF20
A302cyclopropylHCH3CHF20
A303(CH3)3CHCH3CHF20
A304(CH3)2CHHCH3CHF20
A305CH3(CH2)2HCH3CHF20
A306CH3OCH2HCH3CHF20
A307CH3O(CH2)2HCH3CHF20
A308PhHCH3CHF20
A309PhOHCH3CHF20
A310PhSHCH3CHF20
A311PhSOHCH3CHF20
A312PhSO2HCH3CHF20
A313CH3SHCH3CHF20
A314CH3SOHCH3CHF20
A315CF3HCH3CHF20
A316F2CHHCH3CHF20
A317HCCHCH3CHF20
A318CH3CCHCH3CHF20
A319CH2═CHHCH3CHF20
A320CH250 CHCH2HCH3CHF20
A321CH3SO2N(CH3)HCH3CHF20
A322(CH3)2NHCH3CHF20
A323(CH3)2NSO2HCH3CHF20
A324ClCH2HCH3CHF20
A325CH3SCH2HCH3CHF20
A326CH3SOCH2HCH3CHF20
A327CH3SO2CH2HCH3CCl30
A328HHCH3CCl30
A329CH3HCH3CCl30
A330CH3CH2HCH3CCl30
A331(CH3)3CHCH3CCl30
A332(CH3)2CHHCH3CCl30
A333cyclopropylHCH3CCl30
A334CH3(CH2)2HCH3CCl30
A335CH3OCH2HCH3CCl30
A336CH3O(CH2)2HCH3CCl30
A337PhHCH3CCl30
A338PhOHCH3CCl30
A339PbSHCH3CCl30
A340PhSOHCH3CCl30
A341PhSO2HCH3CCl30
A342CH3SHCH3CCl30
A343CH3SOHCH3CCl30
A344CF3HCH3CCl30
A345F2CHHCH3CCl30
A346HCCHCH3CCl30
A347CH3CCHCH3CCl30
A348CH2═CHHCH3CCl30
A349CH2═CHCH2HCH3CCl30
A350CH3SO2N(CH3)HCH3CCl30
A351(CH3)2NHCH3CCl30
A352(CH3)2NSO2HCH3CCl30
A353ClCH2HCH3CCl30
A354CH3SCH2HCH3CCl30
A355CH3SOCH2HCH3CCl30
A356CH3SO2CH2HCH3CCl30
A357HHPhCF30
A358CH3HPhCF30
A359CH3CH2HPhCF30
A360cyclopropylHPhCF30
A361(CH3)3CHPhCF30
A362(CH3)2CHHPhCF30
A363CH3(CH2)2HPhCF30
A364CH3OCH2HPhCF30
A365CH3O(CH2)2HPhCF30
A366PhHPhCF30
A367PhOHPhCF30
A368PhSHPhCF30
A369PhSOHPhCF30
A370PhSO2HPhCF30
A371CH3SHPhCF30
A372CH3SOHPhCF30
A373CF3HPhCF30
A374F2CHHPhCF30
A375HCCHPhCF30
A376CH3CCHPhCF30
A377CH2═CHHPhCF30
A378CH2═CHCH2HPhCF30
A379CH3SO2N(CH3)HPhCF30
A380(CH3)2NHPhCF30
A381(CH3)2NSO2HPhCF30
A382ClCH2HPhCF30
A383CH3SCH2HPhCF30
A384CH3SOCH2HPhCF30
A385CH3SO2CH2HPhCF30
A386HHPhCF3CF20
A387CH3HPhCF3CF20
A388CH3CH2HPhCF3CF20
A389cyclopropylHPhCF3CF20
A390(CH3)3CHPhCF3CF20
A391(CH3)2CHHPhCF3CF20
A392CH3(CH2)2HPhCF3CF20
A393CH3OCH2HPhCF3CF20
A394CH3O(CH2)2HPhCF3CF20
A395PhHPhCF3CF20
A396PhOHPhCF3CF20
A397PhSHPhCF3CF20
A398PhSOHPhCF3CF20
A399PhSO2HPhCF3CF20
A400CH3SHPhCF3CF20
A401CH3SOHPhCF3CF20
A402CF3HPhCF3CF20
A403F2CHHPhCF3CF20
A404HCCHPhCF3CF20
A405CH3CCHPhCF3CF20
A406CH2═CHHPhCF3CF20
A407CH2═CHCH2HPhCF3CF20
A408CH3SO2N(CH3)HPhCF3CF20
A409(CH3)2NHPhCF3CF20
A410(CH3)2NSO2HPhCF3CF20
A411ClCH2HPhCF3CF20
A412CH3SCH2HPhCF3CF20
A413CH3SOCH2HPhCF3CF20
A414CH3SO2CH2HPhCF3CF20
A415HHPhCF3CF2CF20
A416CH3HPhCF3CF2CF20
A417CH3CH2HPhCF3CF2CF20
A418cyclopropylHPhCF3CF2CF20
A419(CH3)3CHPhCF3CF2CF20
A420(CH3)2CHHPhCF3CF2CF20
A421CH3(CH2)2HPhCF3CF2CF20
A422CH3OCH2HPhCF3CF2CF20
A423CH3O(CH2)2HPhCF3CF2CF20
A424PhHPhCF3CF2CF20
A425PhOHPhCF3CF2CF20
A426PhSHPhCF3CF2CF20
A427PhSOHPhCF3CF2CF20
A428PhSO2HPhCF3CF2CF20
A429CH3SHPhCF3CF2CF20
A430CH3SOHPhCF3CF2CF20
A431CF3HPhCF3CF2CF20
A432F2CHHPhCF3CF2CF20
A433HCCHPhCF3CF2CF20
A434CH3CCHPhCF3CF2CF20
A435CH2═CHHPhCF3CF2CF20
A436CH2═CHCH2HPhCF3CF2CF20
A437CH3SO2N(CH3)HPhCF3CF2CF20
A438(CH3)2NHPhCF3CF2CF20
A439(CH3)2NSO2HPhCF3CF2CF20
A440ClCH2HPhCF3CF2CF20
A441CH3SCH2HPhCF3CF2CF20
A442CH3SOCH2HPhCF3CF2CF20
A443CH3SO2CH2HPhCF3CF2CF20
A444HHPhCF2Cl0
A445CH3HPhCF2Cl0
A446CH3CH2HPhCF2Cl0
A447cyclopropylHPhCF2Cl0
A448(CH3)3CHPhCF2Cl0
A449(CH3)2CHHPhCF2Cl0
A450CH3(CH2)2HPhCF2Cl0
A451CH3OCH2HPhCF2Cl0
A452CH3O(CH2)2HPhCF2Cl0
A453PhHPhCF2Cl0
A454PhOHPhCF2Cl0
A455PhSHPhCF2Cl0
A456PhSOHPhCF2Cl0
A457PhSO2HPhCF2Cl0
A458CH3SHPhCF2Cl0
A459CH3SOHPhCF2Cl0
A460CF3HPhCF2Cl0
A461F2CHHPhCF2Cl0
A462HCCHPhCF2Cl0
A463CH3CCHPhCF2Cl0
A464CH2═CHHPhCF2Cl0
A465CH2═CHCH2HPhCF2Cl0
A466CH3SO2N(CH3)HPhCF2Cl0
A467(CH3)2NHPhCF2Cl0
A468(CH3)2NSO2HPhCF2Cl0
A469ClCH2HPhCF2Cl0
A470CH3SCH2HPhCF2Cl0
A471CH3SOCH2HPhCF2Cl0
A472CH3SO2CH2HPhCF2Cl0
A473HHPhCHF20
A474CH3HPhCHF20
A475CH3CH2HPhCHF20
A476cyclopropylHPhCHF20
A477(CH3)3CHPhCHF20
A478(CH3)2CHHPhCHF20
A479CH3(CH2)2HPhCHF20
A480CH3OCH2HPhCHF20
A481CH3O(CH2)2HPhCHF20
A482PhHPhCHF20
A483PhDHPhCHF20
A484PhSHPhCHF20
A485PhSOHPhCHF20
A486PhSO2HPhCHF20
A487CH3SHPhCHF20
A488CH3SOHPhCHF20
A489CF3HPhCHF20
A490F2CHHPhCHF20
A491HCCHPhCHF20
A492CH3CCHPhCHF20
A493CH2═CHHPhCHF20
A494CH2═CHCH2HPhCHF20
A495CH3SO2N(CH3)HPhCHF20
A496(CH3)2NHPhCHF20
A497(CH3)2NSO2HPhCHF20
A498ClCH2HPhCHF20
A499CH3SCH2HPhCHF20
A500CH3SOCH2HPhCHF20
A501CH3SO2CH2HPhCHF20
A502HHPhCCl30
A503CH3HPhCCl30
A504CH3CH2HPhCCl30
A505cyclopropylHPhCCl30
A506(CH3)3CHPhCCl30
A507(CH3)2CHHPhCCl30
A508CH3(CH2)2HPhCCl30
A509CH3CH2HPhCCl30
A510CH3O(CH2)2HPhCCl30
A511PhHPhCCl30
A512PhOHPhCCl30
A513PhSHPhCCl30
A514PhSOHPhCCl30
A515PhSO2HPhCCl30
A516CH3SHPhCCl30
A517CH3SOHPhCCl30
A518CF3HPhCCl30
A519F2CHHPhCCl30
A520HCCHPhCCl30
A521CH3CCHPhCCl30
A522CH2═CHHPhCCl30
A523CH2═CHCH2HPhCCl30
A524CH3SO2N(CH3)HPhCCl30
A525(CH3)2NHPhCCl30
A526(CH3)2NSO2HPhCCl30
A527ClCH2HPhCCl30
A528CH3SCH2HPhCCl30
A529CH3SOCH2HPhCCl30
A530CH3SO2CH2HPhCCl30
A531HCH3HCF30
A532HCH3CH2HCF30
A533HcyclopropylHCF30
A534H(CH3)3CHHCF30
A535H(CH3)2CHHCF30
A536HCH3(CH2)2HCF30
A537HCH3OCH2HCF30
A538HCH3O(CH2)2HCF30
A539HPhHCF30
A540HPhOHCF30
A541HPhSHCF30
A542HPhSOHCF30
A543HPhSO2HCF30
A544HCH3SHCF30
A545HCH3SOHCF30
A546HCF3HCF30
A547HF2CHHCF30
A548HHCCHCF30
A549HCH3CCHCF30
A550HCH2═CHHCF30
A551HCH2═CHCH2HCF30
A552HCH3SO2N(CH3)HCF30
A553H(CH3)2NHCF30
A554H(CH3)2NSO2HCF30
A555HCH3SCH2HCF30
A556HCH3SOCH2HCF30
A557HCH3SO2CH2HCF30
A558HCH3HCF3CF20
A559HCH3CH2HCF3CF20
A560HcyclopropylHCF3CF20
A561H(CH3)3CHCF3CF20
A562H(CH3)2CHHCF3CF20
A563HCH3(CH2)2HCF3CF20
A564HCH3OCH2HCF3CF20
A565HCH3O(CH2)2HCF3CF20
A566HPhHCF3CF20
A567HPhOHCF3CF20
A568HPhSHCF3CF20
A569HPhSOHCF3CF20
A570HPhSO2HCF3CF20
A571HCH3SHCF3CF20
A572HCH3SOHCF3CF20
A573HCF3HCF3CF20
A574HF2CHHCF3CF20
A575HHCCHCF3CF20
A576HCH3CCHCF3CF20
A577HCH2═CHHCF3CF20
A578HCH2CHCH2HCF3CF20
A579HCH3SO2N(CH3)HCF3CF20
A580H(CH3)2NHCF3CF20
A581H(CH3)2NSO2HCF3CF20
A582HCH3SCH2HCF3CF20
A583HCH3SOCH2HCF3CF20
A584HCH3SO2CH2HCF3CF20
A585HCH3HCF3CF2CF20
A586HCH3CH2HCF3CF2CF20
A587HcyclopropylHCF3CF2CF20
A588H(CH3)3CHCF3CF2CF20
A589H(CH3)2CHHCF3CF2CF20
A590HCH3(CH2)2HCF3CF2CF20
A591HCH3OCH2HCF3CF2CF20
A592HCH3O(CH2)2HCF3CF2CF20
A593HPhHCF3CF2CF20
A594HPhOHCF3CF2CF20
A595HPhSHCF3CF2CF20
A596HPhSOHCF3CF2CF20
A597HPhSO2HCF3CF2CF20
A598HCH3SHCF3CF2CF20
A599HCH3SOHCF3CF2CF20
A600HCF3HCF3CF2CF20
A601HF2CHHCF3CF2CF20
A602HHCCHCF3CF2CF20
A603HCH3CCHCF3CF2CF20
A604HCH2═CHHCF3CF2CF20
A605HCH2CHCH2HCF3CF2CF20
A606HCH3SO2N(CH3)HCF3CF2CF20
A607H(CH3)2NHCF3CF2CF20
A608H(CH3)2NSO2HCF3CF2CF20
A609HCH3SCH2HCF3CF2CF20
A610HCH3SOCH2HCF3CF2CF20
A611HCH3SO2CH2HCF3CF2CF20
A612HCH3HCF2Cl0
A613HCH3CH2HCF2Cl0
A614HcyclopropylHCF2Cl0
A615H(CH3)3CHCF2Cl0
A616H(CH3)2CHHCF2Cl0
A617HCH3(CH2)2HCF2Cl0
A618HCH3OCH2HCF2Cl0
A619HCH3O(CH2)2HCF2Cl0
A620HPhHCF2Cl0
A621HPhOHCF2Cl0
A622HPhSHCF2Cl0
A623HPhSOHCF2Cl0
A624HPhSO2HCF2Cl0
A625HCH3SHCF2Cl0
A626HCH3SOHCF2Cl0
A627HCF3HCF2Cl0
A628HF2CHHCF2Cl0
A629HHCCHCF2Cl0
A630HCH3CCHCF2Cl0
A631HCH2═CHHCF2Cl0
A632HCH2═CHCH2HCF2Cl0
A633HCH3SO2N(CH3)HCF2Cl0
A634H(CH3)2NHCF2Cl0
A635H(CH3)2NSO2HCF2Cl0
A636HCH3SCH2HCF2Cl0
A637HCH3SOCH2HCF2Cl0
A638HCH3SO2CH2HCF2Cl0
A639HCH3HCHF20
A640HCH3CH2HCHF20
A641HcyclopropylHCHF20
A642H(CH3)3CHCHF20
A643H(CH3)2CHHCHF20
A644HCH3(CH2)2HCHF20
A645HCH3OCH2HCHF20
A646HCH3O(CH2)2HCHF20
A647HPhHCHF20
A648HPhOHCHF20
A649HPhSHCHF20
A650HPhSOHCHF20
A651HPhSO2HCHF20
A652HCH3SHCHF20
A653HCH3SOHCHF20
A654HCF3HCHF20
A655HF2CHHCHF20
A656HHCCHCHF20
A657HCH3CCHCHF20
A658HCH2═CHHCHF20
A659HCH2═CHCH2HCHF20
A660HCH3SO2N(CH3)HCHF20
A661H(CH3)2NHCHF20
A662H(CH3)2NSO2HCHF20
A663HCH3SCH2HCHF20
A664HCH3SOCH2HCHF20
A665HCH3SO2CH2HCHF20
A666HCH3HCCl30
A667HCH3CH2HCCl30
A668HcyolopropylHCCl30
A669H(CH3)3CHCCl30
A670H(CH3)2CHHCCl30
A671HCH3(CH2)2HCCl30
A672HCH3OCH2HCCl30
A673HCH3O(CH2)2HCCl30
A674HPhHCCl30
A675HPhOHCCl30
A676HPhSHCCl30
A677HPhSOHCCl30
A678HPhSO2HCCl30
A679HCH3SHCCl30
A680HCH3SOHCCl30
A681HCF3HCCl30
A682HF2CHHCCl30
A683HHCCHCCl30
A684HCH3CCHCCl30
A685HCH2═CHHCCl30
A686HCH2═CHCH2HCCl30
A687HCH3SO2N(CH3)HCCl30
A688H(CH3)2NHCCl30
A689H(CH3)2NSO2HCCl30
A690HCH3SCH2HCCl30
A691HCH3SOCH2HCCl30
A692HCH3SO2CH2HCCl30
A693HCH3CH3CF30
A694HCH3CH2CH3CF30
A695HcyclopropylCH3CF30
A696H(CH3)3CCH3CF30
A697H(CH3)2CHCH3CF30
A698HCH3(CH2)2CH3CF30
A699HCH3OCH2CH3CF30
A700HCH3O(CH2)2CH3CF30
A701HPhCH3CF30
A702HPhOCH3CF30
A703HPhSCH3CF30
A704HPhSOCH3CF30
A705HPhSO2CH3CF30
A706HCH3SCH3CF30
A707HCH3SOCH3CF30
A708HCF3CH3CF30
A709HF2CHCH3CF30
A710HHCCCH3CF30
A711HCH3CCCH3CF30
A712HCH2═CHCH3CF30
A713HCH2═CHCH2CH3CF30
A714HCH3SO2N(CH3)CH3CF30
A715H(CH3)2NCH3CF30
A716H(CH3)2NSO2CH3CF30
A717HCH3SCH2CH3CF30
A718HCH3SOCH2CH3CF30
A719HCH3SO2CH2CH3CF30
A720HCH3CH3CF2CF20
A721HCH3CH2CH3CF2CF20
A722HcyclopropylCH3CF2CF20
A723H(CH3)3CCH3CF2CF20
A724H(CH3)2CHCH3CF2CF20
A725HCH3(CH2)2CH3CF2CF20
A726HCH3OCH2CH3CF2CF20
A727HCH3O(CH2)2CH3CF2CF20
A728HPhCH3CF2CF20
A729HPhOCH3CF2CF20
A730HPhSCH3CF2CF20
A731HPhSOCH3CF2CF20
A732HPhSO2CH3CF2CF20
A733HCH3SCH3CF2CF20
A734HCH3SOCH3CF3CF20
A735HCF3CH3CF3CF20
A736HF2CHCH3CF3CF20
A737HHCCCH3CF3CF20
A738HCH3CCCH3CF3CF20
A739HCH2═CHCH3CF3CF20
A740HCH250 CHCH2CH3CF3CF20
A741HCH3SO2N(CH3)CH3CF3CF20
A742H(CH3)2NCH3CF3CF20
A743H(CH3)2NSO2CH3CF3CF20
A744HCH3SCH2CH3CF3CF20
A745HCH3SOCH2CH3CF3CF20
A746HCH3SO2CH2CH3CF3CF20
A747HCH3CH3CF3CF2CF20
A748HCH3CH2CH3CF3CF2CF20
A749HcyclopropylCH3CF3CF2CF20
A750H(CH3)3CCH3CF3CF2CF20
A751H(CH3)2CHCH3CF3CF2CF20
A752HCH3(CH2)2CH3CF3CF2CF20
A753HCH3OCH2CH3CF3CF2CF20
A754HCH3O(CH2)2CH3CF3CF2CF20
A755HPhCH3CF3CF2CF20
A756HPhOCH3CF3CF2CF20
A757HPhSCH3CF3CF2CF20
A758HPhSOCH3CF3CF2CF20
A759HPhSO2CH3CF3CF2CF20
A760HCH3SCH3CF3CF2CF20
A761HCH3SOCH3CF3CF2CF20
A762HCF3CH3CF3CF2CF20
A763HF2CHCH3CF3CF2CF20
A764HHCCCH3CF3CF2CF20
A765HCH3CCCH3CF3CF2CF20
A766HCH2═CHCH3CF3CF2CF20
A767HCH2═CHCH2CH3CF3CF2CF20
A768HCH3SO2N(CH3)CH3CF3CF2CF20
A769H(CH3)2NCH3CF3CF2CF20
A770H(CH3)2NSO2CH3CF3CF2CF20
A771HCH3SCH2CH3CF3CF2CF20
A772HCH3SOCH2CH3CF3CF2CF20
A773HCH3SO2CH2CH3CF3CF2CF20
A774HCH3CH3CF2Cl0
A775HCH3CH2CH3CF2Cl0
A776HcyclopropylCH3CF2Cl0
A777H(CH3)3CCH3CF2Cl0
A778H(CH3)2CHCH3CF2Cl0
A779HCH3(CH2)2CH3CF2Cl0
A780HCH3OCH2CH3CF2Cl0
A781HCH3O(CH2)2CH3CF2Cl0
A782HPhCH3CF2Cl0
A783HPhOCH3CF2Cl0
A784HPhSCH3CF2Cl0
A785HPhSOCH3CF2Cl0
A786HPhSO2CH3CF2Cl0
A787HCH3SCH3CF2Cl0
A788HCH3SOCH3CF2Cl0
A789HCF3CH3CF2Cl0
A790HF2CHCH3CF2Cl0
A791HHCCCH3CF2Cl0
A792HCH3CCCH3CF2Cl0
A793HCH2═CHCH3CF2Cl0
A794HCH2═CHCH2CH3CF2Cl0
A795HCH3SO2N(CH3)CH3CF2Cl0
A796H(CH3)2NCH3CF2Cl0
A797H(CH3)2NSO2CH3CF2Cl0
A798HCH3SCH2CH3CF2Cl0
A799HCH3SOCH2CH3CF2Cl0
A800HCH3SO2CH2CH3CF2Cl0
A801HCH3CH3CHF20
A802HCH3CH2CH3CHF20
A803HcyclopropylCH3CHF20
A804I-i(CH3)3CCH3CHF20
A805H(CH3)2CHCH3CHF20
A806HCH3(CH2)2CH3CHF20
A807HCH3OCH2CH3CHF20
A808HCH3O(CH2)2CH3CHF20
A809HPhCH3CHF20
A810HPhOCH3CHF20
A811HPhSCH3CHF20
A812HPhSOCH3CHF20
A813HPhSO2CH3CHF20
A814HCH3SCH3CHF20
A815HCH3SOCH3CHF20
A816HCF3CH3CHF20
A817HF2CHCH3CHF20
A818HHCCCH3CHF20
A819HCH3CCCH3CHF20
A820HCH2═CHCH3CHF20
A821HCH2═CHCH2CH3CHF20
A822HCH3SO2N(CH3)CH3CHF20
A823H(CH3)2NCH3CHF20
A824H(CH3)2NSO2CH3CHF20
A825HCH3SCH2CH3CHF20
A826HCH3SOCH2CH3CHF20
A827HCH3SO2CH2CH3CHF20
A828HCH3CH3CCl30
A829HCH3CH2CH3CCl30
A830HcyclopropylCH3CCl30
A831H(CH3)3CCH3CCl30
A832H(CH3)2CHCH3CCl30
A833HCH3(CH2)2CH3CCl30
A834HCH3OCH2CH3CCl300
A835HCH3O(CH2)2CH3CCl300
A836HPhCH3CCl300
A837HPhOCH3CCl300
A838HPhSCH3CCl300
A839HPhSOCH3CCl300
A840HPhSO2CH3CCl300
A841HCH3SCH3CCl300
A842HCH3SOCH3CCl300
A843HCF3CH3CCl300
A844HF2CHCH3CCl300
A845HHCCCH3CCl300
A846HCH3CCCH3CCl300
A847HCH2═CHCH3CCl300
A848HCH2═CHCH2CH3CCl300
A849HCH3SO2N(CH3)CH3CCl300
A850H(CH3)2NCH3CCl300
A851H(CH3)2NSO2CH3CCl300
A852HCH3SCH2CH3CCl300
A853HCH3SOCH2CH3CCl300
A854HCH3SO2CH2CH3CCl300
A855HCH3PhCF30
A856HCH3CH2PhCF30
A857H(CH3)2CHPhCF30
A858H(CH3)2CHPhCF30
A859HcyclopropylPhCF30
A860HCH3(CH2)2PhCF30
A861HCH3OCH2PhCF30
A862HCH3O(CH2)2PhCF30
A863HPhPhCF30
A864HPhOPhCF30
A865HPhSPhCF30
A866HPhSOPhCF30
A867HPhSO2PhCF30
A868HCH3SPhCF30
A869HCH3SOPhCF30
A870HCF3PhCF30
A871HF2CHPhCF30
A872HHCCPhCF30
A873HCH3CCPhCF30
A874HCH2═CHPhCF30
A875HCH2═CHCH2PhCF30
A876HCH3SO2N(CH3)PhCF30
A877H(CH3)2NPhCF30
A878H(CH3)2NSO2PhCF30
A879HCH3SCH2PhCF30
A880HCH3SOCH2PhCF30
A881HCH3SO2CH2PhCF30
A882HCH3PhCF3CF20
A883HCH3CH2PhCF3CF20
A884HcyclopropylPhCF3CF20
A885H(CH3)3CPhCF3CF20
A886H(CH3)2CHPhCF3CF20
A887HCH3(CH2)2PhCF3CF20
A888HCH3OCH2PhCF3CF20
A889HCH3O(CH2)2PhCF3CF20
A890HPhPhCF3CF20
A891HPhOPhCF3CF20
A892HPhSPhCF3CF20
A893HPhSOPhCF3CF20
A894HPhSO2PhCF3CF20
A895HCH3SPhCF3CF20
A896HCH3SOPhCF3CF20
A897HCF3PhCF3CF20
A898HF2CHPhCF3CF20
A899HHCCPhCF3CF20
A900HCH3CCPhCF3CF20
A901HCH2═CHPhCF3CF20
A902HCH2═CHCH2PhCF3CF20
A903HCH3SO2N(CH3)PhCF3CF20
A904H(CH3)2NPhCF3CF20
A905H(CH3)2NSO2PhCF3CF20
A906HCH3SCH2PhCF3CF20
A907HCH3SOCH2PhCF3CF20
A908HCH3SO2CH2PhCF3CF20
A909HCH3PhCF3CF2CF20
A910HCH3CH2PhCF3CF2CF20
A911HcyclopropylPhCF3CF2CF20
A912H(CH3)3CPhCF3CF2CF20
A913H(CH3)2CHPhCF3CF2CF20
A914HCH3(CH2)2PhCF3CF2CF20
A915HCH3OCH2PhCF3CF2CF20
A916HCH3O(CH2)2PhCF3CF2CF20
A917HPhPhCF3CF2CF20
A918HPhOPhCF3CF2CF20
A919HPhSPhCF3CF2CF20
A920HPhSOPhCF3CF2CF20
A921HPhSO2PhCF3CF2CF20
A922HCH3SPhCF3CF2CF20
A923HCH3SOPhCF3CF2CF20
A924HCF3PhCF3CF2CF20
A925HF2CHPhCF3CF2CF20
A926HHCCPhCF3CF2CF20
A927HCH3CCPhCF3CF2CF20
A928HCH2═CHPhCF3CF2CF20
A929HCH2═CHCH2PhCF3CF2CF20
A930HCH3SO2N(CH3)PhCF3CF2CF20
A931H(CH3)2NPhCF3CF2CF20
A932H(CH3)2NSO2PhCF3CF2CF20
A933HCH3SCH2PhCF3CF2CF20
A934HCH3SOCH2PhCF3CF2CF20
A935HCH3SO2CH2PhCF3CF2CF20
A936HCH3PhCF2Cl0
A937HCH3CH2PhCF2Cl0
A938HcyclopropylPhCF2Cl0
A939H(CH3)3CPhCF2Cl0
A940H(CH3)2CHPhCF2Cl0
A941HCH3(CH2)2PhCF2Cl0
A942HCH3OCH2PhCF2Cl0
A943HCH3O(CH2)2PhCF2Cl0
A944HPhPhCF2Cl0
A945HPhOPhCF2Cl0
A946HPhSPhCF2Cl0
A947HPhSOPhCF2Cl0
A948HPhSO2PhCF2Cl0
A949HCH3SPhCF2Cl0
A950HCH3SOPhCF2Cl0
A951HCF3PhCF2Cl0
A952HF2CHPhCF2Cl0
A953HHCCPhCF2Cl0
A954HCH3CCPhCF2Cl0
A955HCH2{CHPhCF2Cl0
A956HCH2═CHCH2PhCF2Cl0
A957HCH3SO2N(CH3)PhCF2Cl0
A958H(CH3)2NPhCF2Cl0
A959H(CH3)2NSO2PhCF2Cl0
A960HCH3SCH2PhCF2Cl0
A961HCH3SOCH2PhCF2Cl0
A962HCH3SO2CH2PhCF2Cl0
A963HCH3PhCHF20
A964HCH3CH2PhCHF20
A965H(CH3)3CPhCHF20
A966H(CH3)2CHPhCHF20
A967HcyclopropylPhCHF20
A968HCH3(CH2)2PhCHF20
A969HCH3OCH2PhCHF20
A970HCH3O(CH2)2PhCHF20
A971HPhPhCHF20
A972HPhOPhCHF20
A973HPhSPhCHF20
A974HPhSOPhCHF20
A975HPhSO2PhCHF20
A976HCH3SPhCHF20
A977HCH3SOPhCHF20
A978HCF3PhCHF20
A979HF2CHPhCHF20
A980HHCCPhCHF20
A981HCH3CCPhCHF20
A982HCH2═CHPhCHF20
A983HCH2═CHCH2PhCHF20
A984HCH3SO2N(CH3)PhCHF20
A985H(CH3)2NPhCHF20
A986H(CH3)2NSO2PhCHF20
A987HCH3SCH2PhCHF20
A988HCH3SOCH2PhCHF20
A989HCH3SO2CH2PhCHF20
A990HCH3PhCHF20
A991HCH3CH2PhCCl30
A992H(CH3)3CPhCCl30
A993H(CH3)2CHPhCCl30
A994HcyclopropylPhCCl30
A995HCH3(CH2)2PhCCl30
A996HCH3OCH2PhCCl30
A997HCH3O(CH2)2PhCCl30
A998HPhPhCCl30
A999HPhOPhCCl30
A1000HPhSPhCCl30
A1001HPhSOPhCCl30
A1002HPhSO2PhCCl30
A1003HCH3SPhCCl30
A1004HCH3SOPhCCl30
A1005HCF3PhCCl30
A1006HF2CHPhCCl30
A1007HHCCPhCCl30
A1008HCH3CCPhCCl30
A1009HCH2═CHPhCCl30
A1010HCH2═CHCH2PhCCl30
A1011HCH3SO2N(CH3)PhCCl30
A1012H(CH3)2NPhCCl30
A1013H(CH3)2NSO2PhCCl30
A1014HCH3SCH2PhCCl30
A1015HCH3SOCH2PhCCl30
A1016HCH3SO2CH2PhCCl30
A1017FHHCF30
A1018ClHHCF30
A1019BrHHCF30
A1020NCHHCF30
A1021CH3SO2OHHCF30
A1022CH3OHHCF30
A1023CH3CH2OHHCF30
A1024CH2CH═CH2OHHCF30
A1025HCCCH2CHHCF30
A1026PhCH2SHHCF30
A1027PhCH2SO2HHCF30
A1028ClCH2CH2HHCF30
A1029BrCH2HHCF30
A1030FCH2HHCF30
A1031CHF2CH2HHCF30
A1032CF3CH2HHCF30
A1033[1,3]-imidazol-1-ylmethylHCF30
A1034CHCl2CH2HCF30
A1035ClCH═CHHCF30
A1036Cl2C═CHHHCF30
A1037CF3CH═CHHHCF30
A1038ClCCHHCF30
A1039PhCH2HHCF30
A1040CH3CH2CH3HCF30
A1041CH3OHHCF30
A1042CH3FHCF30
A1043CH3ClHCF30
A1044FCH3HCF30
A1045ClCH3HCF30
A1046HFHCF30
A1047HClHCF30
A1048HBrHCF30
A1049HOHHCF30
A1050HOCH3HCF30
A1051HOCHF2HCF30
A1052HOSO2CH3HCF30
A1053HOSO2CF3HCF30
A1054HClCH2HCF30
A1055HBrCH2HCF30
A1056HFCH2HCF30
A1057HCHF2CH2HCF30
A1058HCF3CH2HCF30
A1059Htriazolylmethyl HCF30
A1060HCHCl2CH2HCF30
A1061HClCH═CHHCF30
A1062HCl2C═CHHCF30
A1063HCF3CH═CHHCF30
A1064HClCCHCF30
A1065HCH3C(O)HCF30
A1066HPhHCF30
A1067HSO2CH3HCF30
A1068HSO2CF3HCF30
A1069HNCHCF30
A1070HNO2HCF30
A1071CH3HFCF30
A1072CH3HClCF30
A1073CH3HBrCF30
A1074CH3HNCCF30
A1075CH3HCH3OCF30
A1076CH3HCH3SCF30
A1077CH3HCH3SOCF30
A1078CH3HCH3SO2CF30
A1079CH3CH2OCH2HHCF30
A1080PhOCH2HHCF30
A1081 42embedded image HHCF30
A1082(CH3)2CH2OCH2HHCF30
A1083BrCH2CH2HHCF30
A1084FCH2CH2HHCF30
A1085 43embedded image HHCF30
A1086 44embedded image HHCF30
A1087 45embedded image HHCF30
A1088 46embedded image HHCF30
A1089 47embedded image HHCF30
A1090 48embedded image HHCF30
A1091cyclopropyl-CH2HHCF30
A10922,2-dichlorocycloprop-1-ylHHCF30
A1093CH3OC(O)CH═CHHHCF30
A1094CH3CH2OC(O)CH═CHHHCF30
A1095ClCH2CH═CHHHCF30
A1096CH═C═CHHHCF30
A1097(CH3)2NCH2HHCF30
A1098HOCH2HHCF30
A1099CH3C(O)OCH2HHCF30
A1100PhC(O)OCH2HHCF30
A1101PhCH2CH2HHCF30
A1102CH3OC(O)CH2HHCF30
A1103NCCH2HHCF30
A1104CH3(CH2)7SCH2HHCF30
A1105CH3(CH2)7SOCH2HHCF30
A1106CH3(CH2)7SO2CH2HHCF30
A1107 49embedded image HHCF30
A1108ClCH2CCHHCF30
A1109CHF2CH2CH2HHCF30
A1110CHCl2CH2CH2HHCF30
A1111CF3SO2OHHCF30
A1112 50embedded image HHCF30
A1113 51embedded image HHCF30
A1114 52embedded image HHCF30
A1115 53embedded image HHCF30
A1116 54embedded image HHCF30
A1117 55embedded image HHCF30
A1118CH3ON═CHCH2HHCF30
A1119O═CHCH2HHCF2Cl0
A1120CH3CH2OCH2HHCF2Cl0
A1121PhOCH2HHCF2Cl0
A1122 56embedded image HHCF2Cl0
A1123(CH3)2CH2OCH2HHCF2Cl0
A1124BrCH2HHCF2Cl0
A1125FCH2HHCF2Cl0
A1126 57embedded image HHCF2Cl0
A1127 58embedded image HHCF2Cl0
A1128 59embedded image HHCF2Cl0
A1129 60embedded image HHCF2Cl0
A1130 61embedded image HHCF2Cl0
A1131 62embedded image HHCF2Cl0
A1132cyclopropyl-CH2HHCF2Cl0
A11332,2-dichlorocycloprop-1-ylHHCF2Cl0
A1134CH3OC(O)CH═OHHHCF2Cl0
A1135CH3CH2OC(O)CH═CHHHCF2Cl0
A1136ClCH2CH═CHHHCF2Cl0
A1137CH═C═CHHHCF2Cl0
A1138(CH3)2NCH2HHCF2Cl0
A1139HOCH2HHCF2Cl0
A1140CH3C(O)OCH2HHCF2Cl0
A1141PhC(O)OCH2HHCF2Cl0
A1142PhCH2HHCF2Cl0
A1143CH3OC(O)CH2HHCF2Cl0
A1144NCCH2HHCF2Cl0
A1145CH3(CH2)7SCH2HHCF2Cl0
A1146CH3(CH2)7SOCH2HHCF2Cl0
A1147CH3(CH2)7SO2CH2HHCF2Cl0
A1148 63embedded image HHCF2Cl0
A1149ClCH2CCHHCF2Cl0
A1150BrHHCF2Cl0
A1151CIHHCF2Cl0
A1152CF3SO2OHHCF2Cl0
A1153 64embedded image HHCF2Cl0
A1154 65embedded image HHCF2Cl0
A1155 66embedded image HHCF2Cl0
A1156 67embedded image HHCF2Cl0
A1157 68embedded image HHCF2Cl0
A1158 69embedded image HHCF2Cl0
A1159CH3ON═CHCH2HHCF2Cl0
A1160O═CHCH2HHCF2Cl0
A1161CH3CH2OCH2HHCF2H0
A1162PhOCH2HHCF2H0
A1163 70embedded image HHCF2H0
A1164(CH3)2CH2OCH2HHCF2H0
A1165BrCH2HHCF2H0
A1166FCH2HHCF2H0
A1167 71embedded image HHCF2H0
A1168 72embedded image HHCF2H0
A1169 73embedded image HHCF2H0
A1170 74embedded image HHCF2H0
A1171 75embedded image HHCF2H0
A1172 76embedded image HHCF2H0
A1173cyclopropyl-CH2HHCF2H0
A11742,2-dichlorocycloprop-1-ylHHCF2H0
A1175CH3OC(O)CH═CHHHCF2H0
A1176CH3CH2OC(O)CH═CHHHCF2H0
A1177ClCH2CH═CHHHCF2H0
A1178CH═C═CHHHCF2H0
A1179(CH3)2NCH2HHCF2H0
A1180HOCH2HHCF2H0
A1181CH3C(O)OCH2HHCF2H0
A1182PhC(O)OCH2HHCF2H0
A1183PhCH2HHCF2H0
A1184CH3OC(O)CH2HHCF2H0
A1185NCCH2HHCF2H0
A1186CH3(CH2)7SCH2HHCF2H0
A1187CH3(CH2)7SOCH2HHCF2H0
A1188CH3(CH2)7SO2CH2HHCF2H0
A1189 77embedded image HHCF2H0
A1190ClCH2CCHHCF2H0
A1191BrHHCF2H0
A1192ClHHCF2H0
A1193CF3SO2OHHCF2H0
A1194 78embedded image HHCF2H0
A1195 79embedded image HHCF2H0
A1196 80embedded image HHCF2H0
A1197 81embedded image HHCF2H0
A1198 82embedded image HHCF2H0
A1199 83embedded image HHCF2H0
A1200CH3ON═CHCH2HHCF2H0
A1201O═CHCH2HHCF2H0
A1202CH3CH═CHHHCF30
A1203CH3SO2NHHHCF30
A1204CH3CH2CH2OHCH3CF30
A1205ClCH3HCF30
A1206F2CHOHHCF30
A1207CH3CH2C(O)OCH2HHCF30
A1208CH3CH2OC(O)OCH2HHCF30
A1209CH3OCH2OCH2HHCF30
A1210CH3HHCF31
A1211CH3CH2HHCF31
A1212cyclopropylHHCF31
A1213CH3(CH2)2HHCF31
A1214CH3OCH2HHCF31
A1215CF3HHCF31
A1216F2CHHHCF31
A1217ClCH2HHCF31
A1218CH3SO2CH2HHCF31
A1219CH3CF3HCF31
A1220CH3CH2OCH2HHCF31
A1221PhOCH2HHCF31
A1222(CH3)2CH2OCH2HHCF31
A1223BrCH2HHCF31
A1224FCH2HHCF31
A1225 84embedded image HHCF31
A1226 85embedded image HHCF31
A1227cyclopropyl-CH2HHCF31
A12282,2-dichlorocycloprop-1-ylHHCF31
A1229(CH3)2NCH2HHCF31
A1230HOCH2HHCF31
A1231CH3C(O)OCH2HHCF31
A1232PhC(O)OCH2HHCF31
A1233PhCH2HHCF31
A1234CH3OC(O)CH2HHCF31
A1235NCCH2HHCF31
A1236CH3(CH2)7SO2CH2HHCF31
A1237BrHHCF31
A1238ClHHCF31
A1239O═CHCHCF2Cl2HHCF31
A1240CH3HHCF2Cl1
A1241CH3CH2HHCF2Cl1
A1242cyclopropylHHCF2Cl1
A1243CH3(CH2)2HHCF2Cl1
A1244CH3OCH2HHCF2Cl1
A1245CF3HHCF2Cl1
A1246F2CHHHCF2Cl1
A1247ClCH2HHCF2Cl1
A1248CH3SO2CH2HHCF2Cl1
A1249CH3CF3HCF2Cl1
A1250CH3CH2OCH2HHCF2Cl1
A1251PhOCH2HHCF2Cl1
A1252(CH3)2CH2OCH2HHCF2Cl1
A1253BrCH2HHCF2Cl1
A1254FCH2HHCF2Cl1
A1255 86embedded image HHCF2Cl1
A1256 87embedded image HHCF2Cl1
A1257cyclopropyl-CH2HHCF2Cl1
A12582,2-dichlorocycloprop-1-ylHHCF2Cl1
A1259(CH3)2NCH2HHCF2Cl1
A1260HOCH2HHCF2Cl1
A1261CH3C(O)OCH2HHCF2Cl1
A1262PhC(O)OCH2HHCF2Cl1
A1263PhCH2HHCF2Cl1
A1264CH3OC(O)CH2HHCF2Cl1
A1265NCCH2HHCF2Cl1
A1266CH3(CH2)7SO2CH2HHCF2Cl1
A1267BrHHCF2Cl1
A1268ClHHCF2Cl1
A1269O═CHCH2HHCF2Cl1
A1270CH3HHCF2H1
A1271CH3CH2HHCF2H1
A1272cyclopropylHHCF2H1
A1273CH3(CH2)2HHCF2H1
A1274CH3OCH2HHCF2H1
A1275CF3HHCF2H1
A1276F2CHHHCF2H1
A1277ClCH2HHCF2H1
A1278CH3SO2CH2HHCF2H1
A1279CH3CF3HCF2H1
A1280CH3CH2OCH2HHCF2H1
A1281PhOCH2HHCF2H1
A1282(CH3)2CH2OCH2HHCF2H1
A1283BrCH2HHCF2H1
A1284FCH2HHCF2H1
A1285 88embedded image HHCF2H1
A1286 89embedded image HHCF2H1
A1287cyclopropyl-CH2HHCF2H1
A12882,2-dichlorocycloprop-1-ylHHCF2H1
A1289(CH3)2NCH2HHCF2H1
A1290HOCH2HHCF2H1
A1291CH3C(O)OCH2HHCF2H1
A1292PhC(O)OCH2HHCF2H1
A1293PhCH2HHCF2H1
A1294CH3OC(O)CH2HHCF2H1
A1295NCCH2HHCF2H1
A1296CH3(CH2)7SO2CH2HHCF2H1
A1297BrHHCF2H1
A1298ClHHCF2H1
A1299O═CHCH2HHCF2H1
A1300CH3HHCF3CF21
A1301HOHPhCF30
A1302CH3HCH2═CHCF30
A1303CH3HCH3CH2OCF30
A1304HOCH3HCF30
A1305HOHHCF30
A1306(CH3CH2)2N(O)COHHCF30
A1307CH3HTosyl-OCF30
A1308CH3HCH3CCCF30
A1309CH3HHCCCF30
A1310CH3HClCH2CCCF30
A1311CH3HPhCH2OCF30
A1312CH3HCF3SO2OCF30
A1313CH3H(CH3)2NCF30
A1314CH3HCH3C(O)OCF30
A1315CH3HCH3CH2C(O)OCF30
A1316CH3HPhC(O)OCF30
A1317CH3H3-PyridylCF30
A1318CH3OCH2OCH2HHCF2Cl0
A1319CH3OCH2OCH2HHCF2H0
A1320CH3OCH2OCH2HHCF2CF30
A1321CH3OCH2OCH2HHCF31
A1322CH3OHCH3CF30

[0220] 2

TABLE 2
Radicals B:
In Table 2 which follows, Q is Q1
90embedded image
and Q1 the radicals B which follow:
RadicalR6R7R8R9R10W
B1HHHHOHCH2
B2CH3HHHOHCH2
B3CH3CH2HHHOHCH2
B4CH3CH2CH2HHHOHCH2
B5(CH3)2CHHHHOHCH2
B6(CH3)3CHHHOHCH2
B7CH3SHHHOHCH2
B8CH3SOHHHOHCH2
B9CH3SO2HHHOHCH2
B10PhHHHOHCH2
B11CH3OHHHOHCH2
B12CH3OC(O)HHHOHCH2
B13CH3CH2OC(O)HHHOHCH2
B14CH2═CHCH2HHHOHCH2
B15HCCCH2HHHOHCH2
B16CF3HHHOHCH2
B17(CH3)2NSO2HHHOHCH2
B18(CH3)2NHHHOHCH2
B19PhOHHHOHCH2
B20PhSHHHOHCH2
B21PhSOHHHOHCH2
B22PhSO2HHHOHCH2
B23CNHHHOHCH2
B24CH3CH3HHOHCH2
B25CH3CH2CH3HHOHCH2
B26CH3CH2CH2CH3HHOHCH2
B27(CH3)2CHCH3HHOHCH2
B28(CH3)3CCH3HHOHCH2
B29CH3SCH3HHOHCH2
B30CH3SOCH3HHOHCH2
B31CH3SO2CH3HHOHCH2
B32PhCH3HHOHCH2
B33CH3OCH3HHOHCH2
B34CH3OC(O)CH3HHOHCH2
B35CH3CH2OC(O)CH3HHOHCH2
B36CH2═CHCH2CH3HHOHCH2
B37HCCCH2CH3HHOHCH2
B38CF3CH3HHOHCH2
B39(CH3)2NSO2CH3HHOHCH2
B40(CH3)2NCH3HHOHCH2
B41PhOCH3HHOHCH2
B42PhSCH3HHOHCH2
B43PhSOCH3HHOHCH2
B44PhSO2CH3HHOHCH2
B45CNCH3HHOHCH2
B46CH3HCH3HOHCH2
B47CH3OH2HCH3HOHCH2
B48CH3CH2CH2HCH3HOHCH2
B49(CH3)2CHHCH3HOHCH2
B50(CH3)3CHCH3HOHCH2
B51CH3SHCH3HOHCH2
B52CH3SOHCH3HOHCH2
B53CH3SO2HCH3HOHCH2
B54PhHCH3HOHCH2
B55CH3OHCH3HOHCH2
B56CH3OC(O)HCH3HOHCH2
B57CH3CH2OC(O)HCH3HOHCH2
B58CH2═CHCH2HCH3HOHCH2
B59HCCCH2HCH3HOHCH2
B60CF3HCH3HOHCH2
B61(CH3)2NSO2HCH3HOHCH2
B62(CH3)2NHCH3HOHCH2
B63PhOHCH3HOHCH2
B64PhSHCH3HOHCH2
B65PhSOHCH3HOHCH2
B66PhSO2HCH3HOHCH2
B67CNHCH3HOHCH2
B68CH3CH3CH3HOHCH2
B69CH3CH2CH3CH3HOHCH2
B70CH3CH2CH2CH3CH3HOHCH2
B71(CH3)2CHCH3CH3HOHCH2
B72(CH3)3CCH3CH3HOHCH2
B73CH3SCH3CH3HOHCH2
B74CH3SOCH3CH3HOHCH2
B75CH3SO2CH3CH3HOHCH2
B76PhCH3CH3HOHCH2
B77CH3OCH3CH3HOHCH2
B78CH3OC(O)CH3CH3HOHCH2
B79CH3CH2OC(O)CH3CH3HOHCH2
B80CH2═CHCH2CH3CH3HOHCH2
B81HCCCH2CH3CH3HOHCH2
B82CF3CH3CH3HOHCH2
B83(CH3)2NSO2CH3CH3HOHCH2
B84(CH3)2NCH3CH3HOHCH2
B85PhOCH3CH3HOHCH2
B86PhSCH3CH3HOHCH2
B87PhSOCH3CH3HOHCH2
B88PhSO2CH3CH3HOHCH2
B89CNCH3CH3HOHCH2
B90CH3CH3CH3CH3OHCH2
B91CH3CH2CH3CH3CH3OHCH2
B92CH3CH2CH2CH3CH3CH3OHCH2
B93(CH3)2CHCH3CH3CH3OHCH2
B94(CH3)3CCH3CH3CH3OHCH2
B95CH3SCH3CH3CH3OHCH2
B96CH3SOCH3CH3CH3OHCH2
B97CH3SO2CH3CH3CH3OHCH2
B98PhCH3CH3CH3OHCH2
B99CH3OCH3CH3CH3OHCH2
B100CH3OC(O)CH3CH3CH3OHCH2
B101CH3CH2OC(O)CH3CH3CH3OHCH2
B102CH2═CHCH2CH3CH3CH3OHCH2
B103HCCCH2CH3CH3CH3OHCH2
B104CF3CH3CH3CH3OHCH2
B105(CH3)2NSO2CH3CH3CH3OHCH2
B106(CH3)2NCH3CH3CH3OHCH2
B107PhOCH3CH3CH3OHCH2
B108PhSCH3CH3CH3OHCH2
B109PhSOCH3CH3CH3OHCH2
B110PhSO2CH3CH3CH3OHCH2
B111ONCH3CH3CH3OHCH2
B112CH3CH2CH3CH2HHOHCH2
B113CH3CH2CH2CH3CH2HHOHCH2
B114(CH3)2CHCH3CH2HHOHCH2
B115(CH3)3CCH3CH2HHOHCH2
B116CH3SCH3CH2HHOHCH2
B117CH3SOCH3CH2HHOHCH2
B118CH3SO2CH3CH2HHOHCH2
B119PhCH3CH2HHOHCH2
B120CH3OCH3CH2HHOHCH2
B121CH3OC(O)CH3CH2HHOHCH2
B122CH3CH2OC(O) CH3CH2HHOHCH2
B123CH2═CHCH2CH3CH2HHOHCH2
B124HCCCH2CH3CH2HHOHCH2
B125CF3CH3CH2HHOHCH2
B126(CH3)2NSO2 CH3CH2HHOHCH2
B127(CH3)2NCH3CH2HHOHCH2
B128PhOCH3CH2HHOHCH2
B129PhSCH3CH2HHOHCH2
B130PhSOCH3CH2HHOHCH2
B131PhSO2CH3CH2HHOHCH2
B132CNCH3CH2HHOHCH2
B133HHHHOHCHCH3
B134CH3HHHOHCHCH3
B135CH3CH2HHHOHCHCH3
B136CH3CH2CH2HHHOHCHCH3
B137(CH3)2CHHHHOHCHCH3
B138(CH3)3OHHHOHCHCH3
B139CH3SHHHOHCHCH3
B140CH3SOHHHOHCHCH3
B141CH3SO2HHHOHCHCH3
B142PhHHHOHCHCH3
B143CH3OHHHOHCHCH3
B144CH3OC(O)HHHOHCHCH3
B145CH3CH2OC(O)HHHOHCHCH3
B146CH2═CHCH2HHHOHCHCH3
B147HCCCH2HHHOHCHCH3
B148CF3HHHOHCHCH3
B149(CH3)2NSO2HHHOHCHCH3
B150(CH3)2NHHHOHCHCH3
B151PhOHHHOHCHCH3
B152PhSHHHOHCHCH3
B153PhSOHHHOHCHCH3
B154PhSO2HHHOHCHCH3
B155CNHHHOHCHCH3
B156CH3CH3HHOHCHCH3
B157CH3CH2CH3HHOHCHCH3
B158CH3CH2CH2CH3HHOHCHCH3
B159(CH3)2CHCH3HHOHCHCH3
B160(CH3)3CCH3HHOHCHCH3
B161CH3SCH3HHOHCHCH3
B162CH3SOCH3HHOHCHCH3
B163CH3SO2CH3HHOHCHCH3
B164PhCH3HHOHCHCH3
B165CH3OCH3HHOHCHCH3
B166CH3OC(O)CH3HHOHCHCH3
B167CH3CH2OC(O)CH3HHOHCHCH3
B168CH250 CHCH2CH3HHOHCHCH3
B169HCCCH2CH3HHOHCHCH3
B170CF3CH3HHOHCHCH3
B171(CH3)2NSO2CH3HHOHCHCH3
B172(CH3)2NCH3HHOHCHCH3
B173PhOCH3HHOHCHCH3
B174PhSCH3HHOHCHCH3
B175PhSOCH3HHOHCHCH3
B176PhSO2CH3HHOHCHCH3
B177CNCH3HHOHCHCH3
B178CH3HCH3HOHCHCH3
B179CH3CH2HCH3HOHCHCH3
B180CH3CH2CH2HCH3HOHCHCH3
B181(CH3)2CHHCH3HOHCHCH3
B182(CH3)3CHCH3HOHCHCH3
B183CH3SHCH3HOHCHCH3
B184CH3SOHCH3HOHCHCH3
B185CH3SO2HCH3HOHCHCH3
B186PhHCH3HOHCHCH3
B187CH3OHCH3HOHCHCH3
B188CH3OC(O)HCH3HOHCHCH3
R189CH3CH3OC(O)HCH3HOHCHCH3
R190CH2═CHCH2HCH3HOHCHCH3
B191HCCCH2HCH3HOHCHCH3
B192CF3HCH3HOHCHCH3
B193(CH3)2NSO2HCH3HOHCHCH3
B194(CH3)2NHCH3HOHCHCH3
B195PhOHCH3HOHCHCH3
B196PhSHCH3HOHCHCH3
B197PhSOHCH3HOHCHCH3
B198PhSO2HCH3HOHCHCH3
B199CNHCH3HOHCHCH3
B200CH3CH3CH3HOHCHCH3
B201CH3CH2CH3CH3HOHCHCH3
B202CH3CH2CH2CH3CH3HOHCHCH3
B203(CH3)2OHCH3CH3HOHCHCH3
B204(CH3)3OCH3CH3HOHCHCH3
B205CH3SCH3CH3HOHCHCH3
B206CH3SOCH3CH3HOHCHCH3
B207CH3SO2CH3CH3HOHCHCH3
B208PhCH3CH3HOHCHCH3
B209CH3OCH3CH3HOHCHCH3
B210CH3OC(O)CH3CH3HOHCHCH3
B211CH3CH2OC(O)CH3CH3HOHCHCH3
B212CH2═CHCH2CH3CH3HOHCHCH3
B213HCCCH2CH3CH3HOHCHCH3
B214CF3CH3CH3HOHCHCH3
B215(CH3)2NSO2CH3CH3HOHCHCH3
B216(CH3)2NCH3CH3HOHCHCH3
B217PhOCH3CH3HOHCHCH3
B218PhSCH3CH3HOHCHCH3
B219PhSOCH3CH3HOHCHCH3
B220PhSO2CH3CH3HOHCHCH3
B221CNCH3CH3HOHCHCH3
B222CH3CH3CH3CH3OHCHCH3
B223CH3CH2CH3CH3CH3OHCHCH3
B224CH3CH2CH2CH3CH3CH3OHCHCH3
B225(CH3)2CHCH3CH3CH3OHCHCH3
B226(CH3)3CCH3CH3CH3OHCHCH3
B227CH3SCH3CH3CH3OHCHCH3
B228CH3SOCH3CH3CH3OHCHCH3
B229CH3SO2CH3CH3CH3OHCHCH3
B230PhCH3CH3CH3OHCHCH3
B231CH3OCH3CH3CH3OHCHCH3
B232CH3OC(O)CH3CH3CH3OHCHCH3
B233CH3CH2OC(O)CH3CH3CH3OHCHCH3
B234CH2═CHCH2CH3CH3CH3OHCHCH3
B235HCCCH2CH3CH3CH3OHCHCH3
B236CF3CH3CH3CH3OHCHCH3
B237(CH3)2NSO2CH3CH3CH3OHCHCH3
B238(CH3)2NCH3CH3CH3OHCHCH3
B239PhOCH3CH3CH3OHCHCH3
B240PhSCH3CH3CH3OHCHCH3
B241PhSOCH3CH3CH3OHCHCH3
B242PhSO2CH3CH3CH3OHCHCH3
B243CNCH3CH3CH3OHCHCH3
B244CH3CH2CH3CH’HHOHCHCH3
B245CH3CH2CH2CH3CH’HHOHCHCH3
B246(CH3)2CHCH3CH’HHOHCHCH3
B247(CH3)3OCH3CH’HHOHCHCH3
B248CH3SCH3CH’HHOHCHCH3
B249CH3SOCH3CH’HHOHCHCH3
B250CH3SO2CH3CH’HHOHCHCH3
B251PhCH3CH’HHOHCHCH3
B252CH3OCH3CH’HHOHCHCH3
B253CH3OC(O)CH3CH’HHOHCHCH3
B254CH3CH2OC(O) CH3CH2HHOHCHCH3
B255CH2═CHCH2CH3CH2HHOHCHCH3
B256HCCCH2CH3CH2HHOHCHCH3
B257CF3CH3CH2HHOHCHCH3
B258(CH3)2NSO2CH3CH2HHOHCHCH3
B259(CH3)2NCH3CH2HHOHCHCH3
B260PhOCH3CH2HHOHCHCH3
B261PhSCH3CH2HHOHCHCH3
B262PhSOCH3CH2HHOHCHCH3
B263PhSO2CH3CH2HHOHCHCH3
B264CNCH3CH2HHOHCHCH3
B265HHHHOHC═O
B266CH3HHHOHC═O
B267CH3CH2HHHOHC═O
B268CH3CH2CH2HHHOHC═O
B269(CH3)2CHHHHOHC═O
B270(CH3)3OHHHOHC═O
B271CH3SHHHOHC═O
B272CH3SOHHHOHC═O
B273CH3SO2HHHOHC═O
B274PhHHHOHC═O
B275CH3OHHHOHC═O
B276CH3OC(O)HHHOHC═O
B277CH3CH2OC(O)HHHOHC═O
B278CH2═CHCH2HHHOHC═O
B279HCCCH2HHHOHC═O
B280CF3HHHOHC═O
B281(CH3)2NSO2HHHOHC═O
B282(CH3)2NHHHOHC═O
B283PhOHHHOHC═O
B284PhSHHHOHC═O
B285PhSOHHHOHC═O
B286PhSO2HHHOHC═O
B287CNHHHOHC═O
B288CH3CH3HHOHC═O
B289CH3CH2CH3HHOHC═O
B290CH3CH2CH2CH3HHOHC═O
B291(CH3)2CHCH3HHOHC═O
B292(CH3)3CCH3HHOHC═O
B293CH3SCH3HHOHC═O
B294CH3SOCH3HHOHC═O
B295CH3SO2CH3HHOHC═O
B296PhCH3HHOHC═O
B297CH3OCH3HHOHC═O
B298CH3OC(O)CH3HHOHC═O
B299CH3CH2OC(O)CH3HHOHC═O
B300CH2═CHCH2CH3HHOHC═O
B301HCCCH2CH3HHOHC═O
B302CF3CH3HHOHC═O
B303(CH3)2NSO2CH3HHOHC═O
B304(CH3)2NCH3HHOHC═O
B305PhOCH3HHOHC═O
B306PhSCH3HHOHC═O
B307PhSOCH3HHOHC═O
B308PhSO2CH3HHOHC═O
B309CNCH3HHOHC═O
B310CH3HCH3HOHC═O
B311CH3CH2HCH3HOHC═O
B312CH3CH2CH2HCH3HOHC═O
B313(CH3)2CHHCH3HOHC═O
B314(CH3)3CHCH3HOHC═O
B315CH3SHCH3HOHC═O
B316CH3SOHCH3HOHC═O
B317CH3SO2HCH3HOHC═O
B318PhHCH3HOHC═O
B319CH3OHCH3HOHC═O
B320CH3OC(O)HCH3HOHC═O
B321CH3CH2OC(O)HCH3HOHC═O
B322CH2═CHCH2HCH3HOHC═O
B323HCCCH2HCH3HOHC═O
B324CF3HCH3HOHC═O
B325(CH3)2NSO2HCH3HOHC═O
B326(CH3)2NHCH3HOHC═O
B327PhOHCH3HOHC═O
B328PhSHCH3HOHC═O
B329PhSOHCH3HOHC═O
B330PhSO2HCH3HOHC═O
B331CNHCH3HOHC═O
B332CH3CH3CH3HOHC═O
B333CH3CH2CH3CH3HOHC═O
B334CH3CH2CH2CH3CH3HOHC═O
B335(CH3)2CHCH3CH3HOHC═O
B336(CH3)3CCH3CH3HOHC═O
B337CH3SCH3CH3HOHC═O
B338CH3SOCH3CH3HOHC═O
B339CH3SO2CH3CH3HOHC═O
B340PhCH3CH3HOHC═O
B341CH3OCH3CH3HOHC═O
B342CH3OC(O)CH3CH3HOHC═O
B343CH3CH2OC(O)CH3CH3HOHC═O
B344CH2═CHCH2CH3CH3HOHC═O
B345HCCCH2CH3CH3HOHC═O
B346CF3CH3CH3HOHC═O
B347(CH3)2NSO2CH3CH3HOHC═O
B348(CH3)2NCH3CH3HOHC═O
B349PhOCH3CH3HOHC═O
B350PhSCH3CH3HOHC═O
B351PhSOCH3CH3HOHC═O
B352PhSO2CH3CH3HOHC═O
B353CNCH3CH3HOHC═O
B354CH3CH3CH3CH3OHC═O
B355CH3CH2CH3CH3CH3OHC═O
B356CH3CH2CH2CH3CH3CH3OHC═O
B357(CH3)2CHCH3CH3CH3OHC═O
B358(CH3)3OCH3CH3CH3OHC═O
B359CH3SCH3CH3CH3OHC═O
B360CH3SOCH3CH3CH3OHC═O
B361CH3SO2CH3CH3CH3OHC═O
B362PhCH3CH3CH3OHC═O
B363CH3OCH3CH3CH3OHC═O
B364CH3OC(O)CH3CH3CH3OHC═O
B365CH3CH2OC(O)CH3CH3CH3OHC═O
B366CH2═CHCH2CH3CH3CH3OHC═O
B367HCCCH2CH3CH3CH3OHC═O
B368CF3CH3CH3CH3OHC═O
B369(CH3)2NSO2CH3CH3CH3OHC═O
B370(CH3)2NCH3CH3CH3OHC═O
B371PhOCH3CH3CH3OHC═O
B372PhSCH3CH3CH3OHC═O
B373PhSOCH3CH3CH3OHC═O
B374PhSO2CH3CH3CH3OHC═O
B375CNCH3CH3CH3OHC═O
B376CH3CH2CH3CH2HHOHC═O
B377CH3CH2CH2CH3CH2HHOHC═O
B378(CH3)2CHCH3CH2HHOHC═O
B379(CH3)3CCH3CH2HHOHC═O
B380CH3SCH3CH2HHOHC═O
B381CH3SOCH3CH2HHOHC═O
B382CH3SO2CH3CH2HHOHC═O
B383PhCH3CH2HHOHC═O
B384CH3OCH3CH2HHOHC═O
B385CH3OC(O)CH3CH2HHOHC═O
B386CH3CH2OC(O) CH3CH2HHOHC═O
B387CH2═CHCH2CH3CH2HHOHC═O
B388HCCCH2CH3CH2HHOHC═O
B389CF3CH3CH2HHOHC═O
B390(CH3)2NSO2 CH3CH2HHOHC═O
B391(CH3)2NCH3CH2HHOHC═O
B392PhOCH3CH2HHOHC═O
B393PhSCH3CH2HHOHC═O
B394PhSOCH3CH2HHOHC═O
B395PhSO2CH3CH2HHOHC═O
B396CNCH3CH2HHOHC═O
B397HHHHOHN—CH3
B398CH3HHHOHN—CH3
B399CH3CH2HHHOHN—CH3
B400CH3CH2CH2HHHOHN—CH3
B401(CH3)2CHHHHOHN—CH3
B402(CH3)3CHHHOHN—CH3
B403CH3SHHHOHN—CH3
B404CH3SOHHHOHN—CH3
B405CH3SO2HHHOHN—CH3
B406PhHHHOHN—CH3
B407CH3OHHHOHN—CH3
B408CH3OC(O)HHHOHN—CH3
B409CH3CH2OC(O)HHHOHN—CH3
B410CH2═CHCH2HHHOHN—CH3
B411HCCCH2HHHOHN—CH3
B412CF3HHHOHN—CH3
B413(CH3)2NSO2HHHOHN—CH3
B414(CH3)2NHHHOHN—CH3
B415PhOHHHOHN—CH3
B416PhSHHHOHN—CH3
B417PhSOHHHOHN—CH3
B418PhSO2HHHOHN—CH3
B419CNHHHOHN—CH3
B420CH3CH3HHOHN—CH3
B421CH3CH2CH3HHOHN—CH3
B422CH3CH2CH2CH3HHOHN—CH3
B423(CH3)2CHCH3HHOHN—CH3
B424(CH3)3CCH3HHOHN—CH3
B425CH3SCH3HHOHN—CH3
B426CH3SOCH3HHOHN—CH3
B427CH3SO2CH3HHOHN—CH3
B428PhCH3HHOHN—CH3
B429CH3OCH3HHOHN—CH3
B430CH3OC(O)CH3HHOHN—CH3
B431CH3CH2OC(O)CH3HHOHN—CH3
B432CH2═CHCH2CH3HHOHN—CH3
B433HCCCH2CH3HHOHN—CH3
B434CF3CH3HHOHN—CH3
B435(CH3)2NSO2CH3HHOHN—CH3
B436(CH3)2NCH3HHOHN—CH3
B437PhOCH3HHOHN—CH3
B438PhSCH3HHOHN—CH3
B439PhSOCH3HHOHN—CH3
B440PhSO2CH3HHOHN—CH3
B441CNCH3HHOHN—CH3
B442CH3HCH3HOHN—CH3
B443CH3CH2HCH3HOHN—CH3
B444CH3CH2CH2HCH3HOHN—CH3
B445(CH3)2CHHCH3HOHN—CH3
B446(CH3)3OHCH3HOHN—CH3
B447CH3SHCH3HOHN—CH3
B448CH3SOHCH3HOHN—CH3
B449CH3SO2HCH3HOHN—CH3
B450PhHCH3HOHN—CH3
B451CH3OHCH3HOHN—CH3
B452CH3OC(O)HCH3HOHN—CH3
B453CH3CH2OC(O)HCH3HOHN—CH3
B454CH2═CHCH2HCH3HOHN—CH3
B455HCCCH2HCH3HOHN—CH3
B456CF3HCH3HOHN—CH3
B457(CH3)2NSO2HCH3HOHN—CH3
B458(CH3)2NHCH3HOHN—CH3
B459PhOHCH3HOHN—CH3
B460PhSHCH3HOHN—CH3
B461PhSOHCH3HOHN—CH3
B462PhSO2HCH3HOHN—CH3
B463CNHCH3HOHN—CH3
B464CH3CH3CH3HOHN—CH3
B465CH3CH2CH3CH3HOHN—CH3
B466CH3CH2CH2CH3CH3HOHN—CH3
B467(CH3)2CHCH3CH3HOHN—CH3
B468(CH3)3CCH3CH3HOHN—CH3
B469CH3SCH3CH3HOHN—CH3
B470CH3SOCH3CH3HOHN—CH3
B471CH3SO2CH3CH3HOHN—CH3
B472PhCH3CH3HOHN—CH3
B473CH3OCH3CH3HOHN—CH3
B474CH3OC(O)CH3CH3HOHN—CH3
B475CH3CH2OC(O)CH3CH3HOHN—CH3
B476CH2═CHCH2CH3CH3HOHN—CH3
B477HCCCH2CH3CH3HOHN—CH3
B478CF3CH3CH3HOHN—CH3
B479(CH3)2NSO2CH3CH3HOHN—CH3
B480(CH3)2NCH3CH3HOHN—CH3
B481PhOCH3CH3HOHN—CH3
B482PhSCH3CH3HOHN—CH3
B483PhSOCH3CH3HOHN—CH3
B484PhSO2CH3CH3HOHN—CH3
B485CNCH3CH3HOHN—CH3
B486CH3CH3CH3CH3OHN—CH3
B487CH3CH2CH3CH3CH3OHN—CH3
B488CH3CH2CH2CH3CH3CH3OHN—CH3
B489(CH3)2CHCH3CH3CH3OHN—CH3
B490(CH3)3CCH3CH3CH3OHN—CH3
B491CH3SCH3CH3CH3OHN—CH3
B492CH3SOCH3CH3CH3OHN—CH3
B493CH3SO2CH3CH3CH3OHN—CH3
B494PhCH3CH3CH3OHN—CH3
B495CH3OCH3CH3CH3OHN—CH3
B496CH3OC(O)CH3CH3CH3OHN—CH3
B497CH3CH2OC(O)CH3CH3CH3OHN—CH3
B498CH2═CHCH2CH3CH3CH3OHN—CH3
B499HCCCH2CH3CH3CH3OHN—CH3
B500CF3CH3CH3CH3OHN—CH3
B501(CH3)2NSO2CH3CH3CH3OHN—CH3
B502(CH3)2NCH3CH3CH3OHN—CH3
B503PhOCH3CH3CH3OHN—CH3
B504PhSCH3CH3CH3OHN—CH3
B505PhSOCH3CH3CH3OHN—CH3
B506PhSO2CH3CH3CH3OHN—CH3
B507CNCH3CH2HHOHN—CH3
B508CH3CH2CH3CH2HHOHN—CH3
B509CH3CH2CH2CH3CH2HHOHN—CH3
B510(CH3)2CHCH3CH2HHOHN—CH3
B511(CH3)3CCH3CH2HHOHN—CH3
B512CH3SCH3CH2HHOHN—CH3
B513CH3SOCH3CH2HHOHN—CH3
B514CH3SO2CH3CH2HHOHN—CH3
B515PhCH3CH2HHOHN—CH3
B516CH3OCH3CH2HHOHN—CH3
B517CH3OC(O)CH3CH2HHOHN—CH3
B518CH3CH2OC(O)CH3CH2HHOHN—CH3
B519CH2═CHCH2CH3CH2HHOHN—CH3
B520HCCCH2CH3CH2HHOHN—CH3
B521CF3CH3CH2HHOHN—CH3
B522(CH3)2NSO2CH3CH2HHOHN—CH3
B523(CH3)2NCH3CH2HHOHN—CH3
B524PhOCH3CH2HHOHN—CH3
B525PhSCH3CH2HHOHN—CH3
B526PhSOCH3CH2HHOHN—CH3
B527PhSO2CH3CH2HHOHN—CH3
B528CNCH3CH2HHOHN—CH3
B529HHHHOHO
B530CH3HHHOHO
B531CH3CH2HHHOHO
B532CH3CH2CH2HHHOHO
B533(CH3)2CHHHHOHO
B534(CH3)3CHHHOHO
B535CH3SHHHOHO
B536CH3SOHHHOHO
B537CH3SO2HHHOHO
B538PhHHHOHO
B539CH3OHHHOHO
B540CH3OC(O)HHHOHO
B541CH3CH2OC(O)HHHOHO
B542CH2═CHCH2HHHOHO
B543HCCCH2HHHOHO
B544CF3HHHOHO
B545(CH3)2NSO2HHHOHO
B546(CH3)2NHHHOHO
B547PhOHHHOHO
B548PhSHHHOHO
B549PhSOHHHOHO
B550PhSO2HHHOHO
B551CNHHHOHO
B552CH3CH3HHOHO
B553CH3CH2CH3HHOHO
B554CH3CH2CH2CH3HHOHO
B555(CH3)2CHCH3HHOHO
B556(CH3)3CCH3HHOHO
B557CH3SCH3HHOHO
B558CH3SOCH3HHOHO
B559CH3SO2CH3HHOHO
B560PhCH3HHOHO
B561CH3OCH3HHOHO
B562CH3OC(O)CH3HHOHO
B563CH3CH2OC(O)CH3HHOHO
B564CH2═CHCH2CH3HHOHO
B565HCCCH2CH3HHOHO
B566CF3CH3HHOHO
B567(CH3)2NSO2CH3HHOHO
B568(CH3)2NCH3HHOHO
B569PhOCH3HHOHO
B570PhSCH3HHOHO
B571PhSOCH3HHOHO
B572PhSO2CH3HHOHO
B573CNCH3HHOHO
B574CH3HCH3HOHO
B575CH3CH2HCH3HOHO
B576CH3CH2CH2HCH3HOHO
B577(CH3)2CHHCH3HOHO
B578(CH3)3OHCH3HOHO
B579CH3SHCH3HOHO
B580CH3SOHCH3HOHO
B581CH3SO2HCH3HOHO
B582PhHCH3HOHO
B583CH3OHCH3HOHO
B584CH3OC(O)HCH3HOHO
B585CH3CH2OC(O)HCH3HOHO
B586CH2═CHCH2HCH3HOHO
B587HCCCH2HCH3HOHO
B588CF3HCH3HOHO
B589(CH3)2NSO2HCH3HOHO
B590(CH3)2NHCH3HOHO
B591PhOHCH3HOHO
B592PhSHCH3HOHO
B593PhSOHCH3HOHO
B594PhSO2HCH3HOHO
B595CNHCH3HOHO
B596CH3CH3CH3HOHO
B597CH3CH2CH3CH3HOHO
B598CH3CH2CH2CH3CH3HOHO
B599(CH3)2CHCH3CH3HOHO
B600(CH3)3CCH3CH3HOHO
B601CH3SCH3CH3HOHO
B602CH3SOCH3CH3HOHO
B603CH3SO2CH3CH3HOHO
B604PhCH3CH3HOHO
B605CH3OCH3CH3HOHO
B606CH3OC(O)CH3CH3HOHO
B607CH3CH2OC(O)CH3CH3HOHO
B608CH2═CHCH2CH3CH3HOHO
B609HCCCH2CH3CH3HOHO
B610CF3CH3CH3HOHO
B611(CH3)2NSO2CH3CH3HOHO
B612(CH3)2NCH3CH3HOHO
B613PhOCH3CH3HOHO
B614PhSCH3CH3HOHO
B615PhSOCH3CH3HOHO
B616PhSO2CH3CH3HOHO
B617CNCH3CH3HOHO
B618CH3CH3CH3CH3OHO
B619CH3CH2CH3CH3CH3OHO
B620CH3CH2CH2CH3CH3CH3OHO
B621(CH3)2OHCH3CH3CH3OHO
B622(CH3)3OCH3CH3CH3OHO
B623CH3SCH3CH3CH3OHO
B624CH3SOCH3CH3CH3OHO
B625CH3SO2CH3CH3CH3OHO
B626PhCH3CH3CH3OHO
B627CH3OCH3CH3CH3OHO
B628CH3OC(O)CH3CH3CH3OHO
B629CH3CH2OC(O)CH3CH3CH3OHO
B630CH2═CHCH2CH3CH3CH3OHO
B631HCCCH2CH3CH3CH3OHO
B632CF3CH3CH3CH3OHO
B633(CH3)2NSO2CH3CH3CH3OHO
B634(CH3)2NCH3CH3CH3OHO
B635PhOCH3CH3CH3OHO
B636PhSCH3CH3CH3OHO
B637PhSOCH3CH3CH3OHO
B638PhSO2CH3CH3CH3OHO
B639CNCH3CH3CH3OHO
B640CH3CH2CH3CH2HHOHO
B641CH3CH2CH2CH3CH2HHOHO
B642(CH3)2CHCH3CH2HHOHO
B643(CH3)3CCH3CH2HHOHO
B644CH3SCH3CH2HHOHO
B645CH3SOCH3CH2HHOHO
B646CH3SO2CH3CH2HHOHO
B647PhCH3CH2HHOHO
B648CH3OCH3CH2HHOHO
B649CH3OC(O)CH3CH2HHOHO
B650CH3CH2OC(O)CH3CH2HHOHO
B651CH2═CHCH2CH3CH2HHOHO
B652HCCCH2CH3CH2HHOHO
B653CF3CH3CH2HHOHO
B654(CH3)2NSO2CH3CH2HHOHO
B655(CH3)2NCH3CH2HHOHO
B656PhOCH3CH2HHOHO
B657PhSCH3CH2HHOHO
B658PhSOCH3CH2HHOHO
B659PhSO2CH3CH2HHOHO
B660CNCH3CH2HHOHO
B661HHHHOHS
B662CH3HHHOHS
B663CH3CH2HHHOHS
B664CH3CH2CH2 HHHOHS
B665(CH3)2CHHHHOHS
B666(CH3)3CHHHOHS
B667CH3SHHHOHS
B668CH3SOHHHOHS
B669CH3SO2HHHOHS
B670PhHHHOHS
B671CH3OHHHOHS
B672CH3OC(O)HHHOHS
B673CH3CH2OC(O)HHHOHS
B674CH2═CHCH2HHHOHS
B675HCCCH2HHHOHS
B676CF3HHHOHS
B677(CH3)2NSO2HHHOHS
B678(CH3)2NHHHOHS
B679PhOHHHOHS
B680PhSHHHOHS
B681PhSOHHHOHS
B682PhSO2HHHOHS
B683CNHCH3HOHS
B684CH3CH3HHOHS
B685CH3CH2CH3HHOHS
B686CH3CH2CH2CH3HHOHS
B687(CH3)2CHCH3HHOHS
B688(CH3)3CCH3HHOHS
B689CH3SCH3HHOHS
B690CH3SOCH3HHOHS
B691CH3SO2CH3HHOHS
B692PhCH3HHOHS
B693CH3OCH3HHOHS
B694CH3OC(O)CH3HHOHS
B695CH3CH2OC(O)CH3HHOHS
B696CH2═CHCH2CH3HHOHS
B697HCCCH2CH3HHOHS
B698CF3CH3HHOHS
B699(CH3)2NSO2CH3HHOHS
B700(CH3)2NCH3HHOHS
B701PhOCH3HHOHS
B702PhSCH3HHOHS
B703PhSOCH3HHOHS
B704PhSO2CH3HHOHS
B705CNCH3HHOHS
B706CH3HCH3HOHS
B707CH3CH2HCH3HOHS
B708CH3CH2CH2HCH3HOHS
B709(CH3)2CHHCH3HOHS
B710(CH3)3CHCH3HOHS
B711CH3SHCH3HOHS
B712CH3SOHCH3HOHS
B713CH3SO2HCH3HOHS
B714PhHCH3HOHS
B715CH3OHCH3HOHS
B716CH3OC(O)HCH3HOHS
B717CH3CH2OC(O)HCH3HOHS
B718CH2═CHCH2HCH3HOHS
B719HCCCH2HCH3HOHS
B720CF3HCH3HOHS
B721(CH3)2NSO2HCH3HOHS
B722(CH3)2NHCH3HOHS
B723PhOHCH3HOHS
B724PhSHCH3HOHS
B725PhSOHCH3HOHS
B726PhSO2HCH3HOHS
B727CNHCH3HOHS
B728CH3CH3CH3HOHS
B729CH3CH2CH3CH3HOHS
B730CH3CH2CH2CH3CH3HOHS
B731(CH3)2CHCH3CH3HOHS
B732(CH3)3CCH3CH3HOHS
B733CH3SCH3CH3HOHS
B734CH3SOCH3CH3HOHS
B735CH3SO2CH3CH3HOHS
B736PhCH3CH3HOHS
B737CH3OCH3CH3HOHS
B738CH3OC(O)CH3CH3HOHS
B739CH3CH2OC(O)CH3CH3HOHS
B740CH2═CHCH2CH3CH3HOHS
B741HCCCH2CH3CH3HOHS
B742CF3CH3CH3HOHS
B743(CH3)2NSO2CH3CH3HOHS
B744(CH3)2NCH3CH3HOHS
B745PhOCH3CH3HOHS
B746PhSCH3CH3HOHS
B747PhSOCH3CH3HOHS
B748PhSO2CH3CH3HOHS
B749CNCH3CH3HOHS
B750CH3CH3CH3CH3OHS
B751CH3CH2CH3CH3CH3OHS
B752CH3CH2CH2CH3CH3CH3OHS
B753(CH3)2CHCH3CH3CH3OHS
B754(CH3)3CCH3CH3CH3OHS
B755CH3SCH3CH3CH3OHS
B756CH3SOCH3CH3CH3OHS
B757CH3SO2CH3CH3CH3OHS
B758PhCH3CH3CH3OHS
B759CH3OCH3CH3CH3OHS
B760CH3OC(O)CH3CH3CH3OHS
B761CH3CH2OC(O)CH3CH3CH3OHS
B762CH2═CHCH2CH3CH3CH3OHS
B763HCCCH2CH3CH3CH3OHS
B764CF3CH3CH3CH3OHS
B765(CH3)2NSO2CH3CH3CH3OHS
B766(CH3)2NCH3CH3CH3OHS
B767PhOCH3CH3CH3OHS
B768PhSCH3CH3CH3OHS
B769PhSOCH3CH3CH3OHS
B770PhSO2CH3CH3CH3OHS
B771CNCH3CH3CH3OHS
B772CH3CH2CH3CH2HHOHS
B773CH3CH2CH2CH3CH2HHOHS
B774(CH3)2CHCH3CH2HHOHS
B775(CH3)3CCH3CH2HHOHS
B776CH3SCH3CH2HHOHS
B777CH3SOCH3CH2HHOHS
B778CH3SO2CH3CH2HHOHS
B779PhCH3CH2HHOHS
B780CH3OCH3CH2HHOHS
B781CH3OC(O)CH3CH2HHOHS
B782CH3CH2OC(O)CH3CH2HHOHS
B783CH2═CHCH2CH3CH2HHOHS
B784HCCCH2CH3CH2HHOHS
B785CF3CH3CH2HHOHS
B786(CH3)2NSO2CH3CH2HHOHS
B787(CH3)2NCH3CH2HHOHS
B788PhOCH3CH2HHOHS
B789PhSCH3CH2HHOHS
B790PhSOCH3CH2HHOHS
B791PhSO2CH3CH2HHOHS
B792CNCH3CH2HHOHS
B793HHHHOHSO2
B794CH3HHHOHSO2
B795CH3CH2HHHOHSO2
B796CH3CH2CH2HHHOHSO2
B797(CH3)2CHHHHOHSO2
B798(CH3)3CHHHOHSO2
B799CH3SHHHOHSO2
B800CH3SOHHHOHSO2
B801CH3SO2HHHOHSO2
B802PhHHHOHSO2
B803CH3OHHHOHSO2
B804CH3OC(O)HHHOHSO2
B805CH3CH2OC(O)HHHOHSO2
B806CH2═CHCH2HHHOHSO2
B807HCCCH2HHHOHSO2
B808CF3HHHOHSO2
B809(CH3)2NSO2HHHOHSO2
B810(CH3)2NHHHOHSO2
B811PhOHHHOHSO2
B812PhSHHHOHSO2
B813PhSOHHHOHSO2
B814PhSO2HHHOHSO2
B815CNHHHOHSO2
B816CH3CH3HHOHSO2
B817CH3CH2CH3HHOHSO2
B818CH3CH2CH2CH3HHOHSO2
B819(CH3)2CHCH3HHOHSO2
B820(CH3)3CCH3HHOHSO2
B821CH3SCH3HHOHSO2
B822CH3SOCH3HHOHSO2
B823CH3SO2CH3HHOHSO2
B824PhCH3HHOHSO2
B825CH3OCH3HHOHSO2
B826CH3OC(O)CH3HHOHSO2
B827CH3CH2OC(O)CH3HHOHSO2
B828CH2═CHCH2CH3HHOHSO2
B829HCCCH2CH3HHOHSO2
B830CF3CH3HHOHSO2
B831(CH3)2NSO2CH3HHOHSO2
B832(CH3)2NCH3HHOHSO2
B833PhOCH3HHOHSO2
B834PhSCH3HHOHSO2
B835PhSOCH3HHOHSO2
B836PhSO2CH3HHOHSO2
B837CNCH3HHOHSO2
B838CH3HCH3HOHSO2
B839CH3CH2HCH3HOHSO2
B840CH3CH2CH2HCH3HOHSO2
B841(CH3)2CHHCH3HOHSO2
B842(CH3)3CHCH3HOHSO2
B843CH3SHCH3HOHSO2
B844CH3SOHCH3HOHSO2
B845CH3SO2HCH3HOHSO2
B846PhHCH3HOHSO2
B847CH3OHCH3HOHSO2
B848CH3OC(O)HCH3HOHSO2
B849CH3CH2OC(O)HCH3HOHSO2
B850CH2═CHCH2HCH3HOHSO2
B851HCCCH2HCH3HOHSO2
B852CF3HCH3HOHSO2
B853(CH3)2NSO2HCH3HOHSO2
B854(CH3)2NHCH3HOHSO2
B855PhOHCH3HOHSO2
B856PhSHCH3HOHSO2
B857PhSOHCH3HOHSO2
B858PhSO2HCH3HOHSO2
B859CNHCH3HOHSO2
B860CH3CH3CH3HOHSO2
B861CH3CH2CH3CH3HOHSO2
B862CH3CH2CH2CH3CH3HOHSO2
B863(CH3)2CHCH3CH3HOHSO2
B864(CH3)3CCH3CH3HOHSO2
B865CH3SCH3CH3HOHSO2
B866CH3SOCH3CH3HOHSO2
B867CH3SO2CH3CH3HOHSO2
B868PhCH3CH3HOHSO2
B869CH3OCH3CH3HOHSO2
B870CH3OC(O)CH3CH3HOHSO2
B871CH3CH2OC(O)CH3CH3HOHSO2
B872CH2═CHCH2CH3CH3HOHSO2
B873HCCCH2CH3CH3HOHSO2
B874CF3CH3CH3HOHSO2
B875(CH3)2NSO2CH3CH3HOHSO2
B876(CH3)2NCH3CH3HOHSO2
B877PhOCH3CH3HOHSO2
B878PhSCH3CH3HOHSO2
B879PhSOCH3CH3HOHSO2
B880PhSO2CH3CH3HOHSO2
B881CNCH3CH3HOHSO2
B882CH3CH3CH3CH3OHSO2
B883CH3CH2CH3CH3CH3OHSO2
B884CH3CH2CH2CH3CH3CH3OHSO2
B885(CH3)2CHCH3CH3CH3OHSO2
B886(CH3)3CCH3CH3CH3OHSO2
B887CH3SCH3CH3CH3OHSO2
B888CH3SOCH3CH3CH3OHSO2
B889CH3SO2CH3CH3CH3OHSO2
B890PhCH3CH3CH3OHSO2
B891CH3OCH3CH3CH3OHSO2
B892CH3OC(O)CH3CH3CH3OHSO2
B893CH3CH2OC(O)CH3CH3CH3OHSO2
B894CH2═CHCH2CH3CH3CH3OHSO2
B895HCCCH2CH3CH3CH3OHSO2
B896CF3CH3CH3CH3OHSO2
B897(CH3)2NSO2CH3CH3CH3OHSO2
B898(CH3)2NCH3CH3CH3OHSO2
B899PhOCH3CH3CH3OHSO2
B900PhSCH3CH3CH3OHSO2
B901PhSOCH3CH3CH3OHSO2
B902PhSO2CH3CH3CH3OHSO2
B903CNCH3CH3CH3OHSO2
B904CH3CH2CH3CH2HHOHSO2
B905CH3CH2CH2CH3CH2HHOHSO2
B906(CH3)2CHCH3CH2HHOHSO2
B907(CH3)3CCH3CH2HHOHSO2
B908CH3SCH3CH2HHOHSO2
B909CH3SOCH3CH2HHOHSO2
B910CH3SO2CH3CH2HHOHSO2
B911PhCH3CH2HHOHSO2
B912CH3OCH3CH2HHOHSO2
B913CH3OC(O)CH3CH2HHOHSO2
B914CH3CH2OC(O)CH3CH2HHOHSO2
B915CH2═CHCH2CH3CH2HHOHSO2
B916HCCCH2CH3CH2HHOHSO2
B917CF3CH3CH2HHOHSO2
B918(CH3)2NSO2CH3CH2HHOHSO2
B919(CH3)2NCH3CH2HHOHSO2
B920PhOCH3CH2HHOHSO2
B921PhSCH3CH2HHOHSO2
B922PhSOCH3CH2HHOHSO2
B923PhSO2CH3CH2HHOHSO2
B924CNCH3CH2HHOHSO2
B925HHHHOHCHC(O)OCH2CH3
B926CH3HHHOHCHC(O)OCH2CH3
B927CH3CH2HHHOHCHC(O)OCH2CH3
B928CH3CH2CH2HHHOHCHC(O)OCH2CH3
B929(CH3)2CHHHHOHCHC(O)OCH2CH3
B930(CH3)3CHHHOHCHC(O)OCH2CH3
B931CH3SHHHOHCHC(O)OCH2CH3
B932CH3SOHHHOHCHC(O)OCH2CH3
B933CH3SO2HHHOHCHC(O)OCH2CH3
B934PhHHHOHCHC(O)OCH2CH3
B935CH3OHHHOHCHC(O)OCH2CH3
B936CH3OC(O)HHHOHCHC(O)OCH2CH3
B937CH3CH2OC(O)HHHOHCHC(O)OCH2CH3
B938CH2═CHCH2HHHOHCHC(O)OCH2CH3
B939HCCCH2HHHOHCHC(O)OCH2CH3
B940CF3HHHOHCHC(O)OCH2CH3
B941(CH3)2NSO2HHHOHCHC(O)OCH2CH3
B942(CH3)2NHHHOHCHC(O)OCH2CH3
B943PhOHHHOHCHC(O)OCH2CH3
B944PhSHHHOHCHC(O)OCH2CH3
B945PhSOHHHOHCHC(O)OCH2CH3
B946PhSO2HHHOHCHC(O)OCH2CH3
B947CNHHHOHCHC(O)OCH2CH3
B948CH3CH3HHOHCHC(O)OCH2CH3
B949CH3CH2CH3HHOHCHC(O)OCH2CH3
B950CH3CH2CH2CH3HHOHCHC(O)OCH2CH3
B951(CH3)2CHCH3HHOHCHC(O)OCH2CH3
B952(CH3)3CCH3HHOHCHC(O)OCH2CH3
B953CH3SCH3HHOHCHC(O)OCH2CH3
B954CH3SOCH3HHOHCHC(O)OCH2CH3
B955CH3SO2CH3HHOHCHC(O)OCH2CH3
B956PhCH3HHOHCHC(O)OCH2CH3
B957CH3OCH3HHOHCHC(O)OCH2CH3
B958CH3OC(O)CH3HHOHCHC(O)OCH2CH3
B959CH3CH2OC(O)CH3HHOHCHC(O)OCH2CH3
B960CH2═CHCH2CH3HHOHCHC(O)OCH2CH3
B961HCCCH2CH3HHOHCHC(O)OCH2CH3
B962CF3CH3HHOHCHC(O)OCH2CH3
B963(CH3)2NSO2CH3HHOHCHC(O)OCH2CH3
B964(CH3)2NCH3HHOHCHC(O)OCH2CH3
B965PhOCH3HHOHCHC(O)OCH2CH3
B966PhSCH3HHOHCHC(O)OCH2CH3
B967PhSOCH3HHOHCHC(O)OCH2CH3
B968PhSO2CH3HHOHCHC(O)OCH2CH3
B969CNCH3HHOHCHC(O)OCH2CH3
B970CH3CH3HHOHCHC(O)OCH2CH3
B971CH3CH2HCH3HOHCHC(O)OCH2CH3
B972CH3CH2CH2HCH3HOHCHC(O)OCH2CH3
B973(CH3)2CHHCH3HOHCHC(O)OCH2CH3
B974(CH3)3OHCH3HOHCHC(O)OCH2CH3
B975CH3SHCH3HOHCHC(O)OCH2CH3
B976CH3SOHCH3HOHCHC(O)OCH2CH3
B977CH3SO2HCH3HOHCHC(O)OCH2CH3
B978PhHCH3HOHCHC(O)OCH2CH3
B979CH3OHCH3HOHCHC(O)OCH2CH3
B980CH3OC(O)HCH3HOHCHC(O)OCH2CH3
B981CH3CH2OC(O)HCH3HOHCHC(O)OCH2CH3
B982CH2CHCH2HCH3HOHCHC(O)OCH2CH3
B983HCCCH2HCH3HOHCHC(O)OCH2CH3
B984CF3HCH3HOHCHC(O)OCH2CH3
B985(CH3)2NSO2HCH3HOHCHC(O)OCH2CH3
B986(CH3)2NHCH3HOHCHC(O)OCH2CH3
B987PhOHCH3HOHCHC(O)OCH2CH3
B988PhSHCH3HOHCHC(O)OCH2CH3
B989PhSOHCH3HOHCHC(O)OCH2CH3
B990PhSO2HCH3HOHCHC(O)OCH2CH3
B991CNHCH3HOHCHC(O)OCH2CH3
B992CH3CH3CH3HOHCHC(O)OCH2CH3
B993CH3CH2CH3CH3HOHCHC(O)OCH2CH3
B994CH3CH2CH2CH3CH3HOHCHC(O)OCH2CH3
B995(CH3)2CHCH3CH3HOHCHC(O)OCH2CH3
B996(CH3)3CCH3CH3HOHCHC(O)OCH2CH3
B997CH3SCH3CH3HOHCHC(O)OCH2CH3
B998CH3SOCH3CH3HOHCHC(O)OCH2CH3
B999CH3SO2CH3CH3HOHCHC(O)OCH2CH3
B1000PhCH3CH3HOHCHC(O)OCH2CH3
B1001CH3OCH3CH3HOHCHC(O)OCH2CH3
B1002CH3OC(O)CH3CH3HOHCHC(O)OCH2CH3
B1003CH3CH2OC(O)CH3CH3HOHCHC(O)OCH2CH3
B1004CH2CHCH2CH3CH3HOHCHC(O)OCH2CH3
B1005HCCCH2CH3CH3HOHCHC(O)OCH2CH3
B1006CF3CH3CH3HOHCHC(O)OCH2CH3
B1007(CH3)2NSO2CH3CH3HOHCHC(O)OCH2CH3
B1008(CH3)2NCH3CH3HOHCHC(O)OCH2CH3
B1009PhOCH3CH3HOHCHC(O)OCH2CH3
B1010PhSCH3CH3HOHCHC(O)OCH2CH3
B1011PhSOCH3CH3HOHCHC(O)OCH2CH3
B1012PhSO2CH3CH3HOHCHC(O)OCH2CH3
B1013CNCH3CH3HOHCHC(O)OCH2CH3
B1014CH3CH3CH3CH3OHCHC(O)OCH2CH3
B1015CH3CH2CH3CH3CH3OHCHC(O)OCH2CH3
B1016CH3CH2CH2CH3CH3CH3OHCHC(O)OCH2CH3
B1017(CH3)2CHCH3CH3CH3OHCHC(O)OCH2CH3
B1018(CH3)3CCH3CH3CH3OHCHC(O)OCH2CH3
B1019CH3SCH3CH3CH3OHCHC(O)OCH2CH3
B1020CH3SOCH3CH3CH3OHCHC(O)OCH2CH3
B1021CH3SO2CH3CH3CH3OHCHC(O)OCH2CH3
B1022PhCH3CH3CH3OHCHC(O)OCH2CH3
B1023CH3OCH3CH3CH3OHCHC(O)OCH2CH3
B1024CH3OC(O)CH3CH3CH3OHCHC(O)OCH2CH3
B1025CH3CH2OC(O) CH3CH3CH3OHCHC(O)OCH2CH3
B1026CH2═CHCH2 CH3CH3CH3OHCHC(O)OCH2CH3
B1027HCCCH2CH3CH3CH3OHCHC(O)OCH2CH3
B1028CF3CH3CH3CH3OHCHC(O)OCH2CH3
B1029(CH3)2NSO2CH3CH3CH3OHCHC(O)OCH2CH3
B1030(CH3)2NCH3CH3CH3OHCHC(O)OCH2CH3
B1031PhOCH3CH3CH3OHCHC(O)OCH2CH3
B1032PhSCH3CH3CH3OHCHC(O)OCH2CH3
B1033PhSOCH3CH3CH3OHCHC(O)OCH2CH3
B1034PhSO2CH3CH3CH3OHCHC(O)OCH2CH3
B1035CNCH3CH3CH3OHCHC(O)OCH2CH3
B1036CH3CH2CH3CH2HHOHCHC(O)OCH2CH3
B1037CH3CH2CH2CH3CH2HHOHCHC(O)OCH2CH3
B1038(CH3)2CHCH3CH2HHOHCHC(O)OCH2CH3
B1039(CH3)3CCH3CH2HHOHCHC(O)OCH2CH3
B1040CH3SCH3CH2HHOHCHC(O)OCH2CH3
B1041CH3SOCH3CH2HHOHCHC(O)OCH2CH3
B1042CH3SO2CH3CH2HHOHCHC(O)OCH2CH3
B1043PhCH3CH2HHOHCHC(O)OCH2CH3
B1044CH3OCH3CH2HHOHCHC(O)OCH2CH3
B1045CH3OC(O)CH3CH2HHOHCHC(O)OCH2CH3
B1046CH3CH2OC(O)CH3CH2HHOHCHC(O)OCH2CH3
B1047CH2═CHCH2CH3CH2HHOHCHC(O)OCH2CH3
B1048HCCCH2CH3CH2HHOHCHC(O)OCH2CH3
B1049CF3CH3CH2HHOHCHC(O)OCH2CH3
B1050(CH3)2NSO2 CH3CH2HHOHCHC(O)OCH2CH3
B1051(CH3)2NCH3CH2HHOHCHC(O)OCH2CH3
B1052PhOCH3CH2HHOHCHC(O)OCH2CH3
B1053PhSCH3CH2HHOHCHC(O)OCH2CH3
B1054PhSOCH3CH2HHOHCHC(O)OCH2CH3
B1055PhSO2CH3CH2HHOHCHC(O)OCH2CH3
B1056CNCH3CH2HHOHCHC(O)OCH2CH3
B1057CH3OC(O)HHHOHCHPh
B1058HHHHOHCHPh
B1059HHHHOHCH(CH2CH3)
B1060HHHHOHCH(CH2CH2CH3)
B1061HHHHOHCH(CH(CH3)2)
B1062HHHHOHCH(C(CH3)2)
B1063HHHHOHC(CH3)2
B1064HHHHOHCH(CF3)
B1065CH3OC(O)HHHOHC(CH3)(CF3)
B1066HHHHOHC(CH3)(CF3)
B1067CH3OC(O)CH3OHHOHCH2
B1068HCH3OHHOHCH2
B1069CH3O CH3OC(O)HCH3OHCH2
B1070CH3OHCH3HOHCH2
B1071ClHHHOHCH2
B1072FHHHOHCH2
B1073HHHHOHCH(OCH3)2
B1074HHHHOHCH2OSO2CH3
B1075CH3CH3CH3CH3OHCH2
B1076ClCH2CH2CH3CH3CH3OHCH2
B1077HO(CH2)2CH3CH3CH3OHCH2
B1078MsO(CH2)2 CH3CH3CH3OHCH2
B1079HOCH(CH3)CH2HHHOHCH2
B1080MsOCH(CH3)CH2HHHOHCH2
B1081(CH3)2CHHCH3CH3OHCH2
B1082HCCCH2HCH3CH3OHCH2
B1083H2C═CCH2HCH3CH3OHCH2
B1084H2C═C(CH3)HHHOHCHCH3
B1085HHHHOHCHCONHCH2Ph
B1086HHHHOH 91embedded image
B1087CH3OC(O)CH3HHOHC(CH3)2
B1088HHHHOH 92embedded image
B1089CH3CH2HCH3CH3OHCH2
B1090CH3OC(O)HHHOHCF3CH2CH2
B1091CH3CH2SCH3CH2CH3HOHCH2
B1092CH3SPhCH3HOHCH2
B1093CH3CH2CH3CH2CH3HOHCH2
B1094CH3OC(O)HHHOHC(CH3)2
B1095CH3HHHOHC(CH3)2
B1096HHHHOHNCOCH2SCH3
B1097 93embedded image HHHOHCH2
B10981,1-dimethylvinylHHHOHCH2
B1099 94embedded image HHHOHCH2
B1100HHHH—ONH + (CH2CH3)3CH2
B1101HHHH—ONH + (CH2CH3)3CH(CH3)
B1102HHHHPhSCH2
B1103HHHHPhSOCH2
B1104HHHHPhSO2CH2
B1105CH3CH3CH3CH3ClC═O
B1106HHHHOHCHCH2CH(CH3)2
B1107CH3CH3CH3CH3CH3C(O)OC═O
B1108CH3OC(O)CH2HHHOHCH2
B1109CH3OC(O)CH2CH3HHOHCH2
B1110CH3OC(O)CH2CH3CH3HOHCH2
B1111CH3OC(O)CH2CH3CH3CH3OHCH2
B1112CH3OC(O)CH2HCH3CH3OHCH2
B1113CH3OC(O)CH2HHHOHCH(CH3)
B1114CH3OC(O)CH2CH3HHOHCH(CH3)
B1115CH3OC(O)CH2CH3CH3HOHCH(CH3)
B1116CH3OC(O)CH2CH3CH3CH3OHCH(CH3)
B1117CH3OC(O)CH2HCH3CH3OHCH(CH3)
B1118CH3OC(O)CH2HHHOHC(CH3)2
B1119CH3OC(O)CH2CH3HHOHC(CH3)2
B1120CH3OC(O)CH2CH3CH3HOHC(CH3)2
B1121CH3OC(O)CH2CH3CH3CH3OHC(CH3)2
B1122CH3OC(O)CH2HCH3CH3OHC(CH3)2
B1123CH3CH2OC(O)CH2HHHOHCH2
B1124CH3CH2OC(O)CH2CH3HHOHCH2
B1125CH3CH2OC(O)CH2CH3CH3HOHCH2
B1126CH3CH2OC(O)CH2CH3CH3CH3OHCH2
B1127CH3CH2OC(O)CH2HCH3CH3OHCH2
B1128CH3CH2OC(O)CH2HHHOHCH(CH3)
B1129CH3CH2OC(O)CH2CH3HHOHCH(CH3)
B1130CH3CH2OC(O)CH2CH3CH3HOHCH(CH3)
B1131CH3CH2OC(O)CH2CH3CH3CH3OHCH(CH3)
B1132CH3CH2OC(O)CH2HCH3CH3OHCH(CH3)
B1133CH3CH2OC(O)CH2HHHOHC(CH3)2
B1134CH3CH2OC(O)CH2CH3HHOHC(CH3)2
B1135CH3CH2OC(O)CH2CH3CH3HOHC(CH3)2
B1136CH3CH2OC(O)CH2CH3CH3CH3OHC(CH3)2
B1137CH3CH2OC(O)CHHCH3CH3OHC(CH3)2
B1138 95embedded image CH3HHOHCH2
B1139CH3SCH2HHHOHCH2
B1140CH3SCH2CH3HHOHCH2
B1141CH3SCH2CH3CH3HOHCH2
B1142CH3SCH2CH3CH3CH3OHCH2
B1143CH3SCH2HCH3CH3OHCH2
B1144CH3SOCH2HHHOHCH2
B1145CH3SOCH2CH3HHOHCH2
B1146CH3SOCH2CH3CH3HOHCH2
B1147CH3SOCH2CH3CH3CH3OHCH2
B1148CH3SOCH2HCH3CH3OHCH2
B1149CH3SOCH2HHHOHCH2
B1150CH3SOCH2CH3HHOHCH2
B1151CH3SOCH2CH3CH3HOHCH2
B1152CH3SOCH2CH3CH3CH3OHCH2
B1153CH3SOCH2HCH3CH3OHCH2
B1154HOCH2HHHOHCH2
B1155HOCH2CH3HHOHCH2
B1156HOCH2CH3CH3HOHCH2
B1157HOCH2CH3CH3CH3OHCH2
B1158HOCH2HCH3CH3OHCH2
B1159NCCH2HHHOHCH2
B1160NCCH2CH3HHOHCH2
B1161NCCH2CH3CH3HOHCH2
B1162NCCH2CH3CH3CH3OHCH2
B1163NCCH2HCH3CH3OHCH2
B1164CH3C(O)OCH2HHHOHCH2
B1165CH3C(O)OCH2CH3HHOHCH2
B1166CH3C(O)OCH2CH3CH3HOHCH2
B1167CH3C(O)OCH2CH3CH3CH3OHCH2
B1168CH3C(O)OCH2HCH3CH3OHCH2
B1169CH3OCH2HHHOHCH2
B1170CH3OCH2CH3HHOHCH2
B1171CH3OCH2CH3CH3HOHCH2
B1172CH3OCH2CH3CH3CH3OHCH2
B1173CH3OCH2HCH3CH3OHCH2
B1174PhCH2HHHOHCH2
B1175PhCH2CH3HHOHCH2
B1176PhCH2CH3CH3HOHCH2
B1177PhCH2CH3CH3CH3OHCH2
B1178PhCH2HCH3CH3OHCH2
B1179HHHHO—K+CH2
B1180HHHHS(CH2)7CH3CH2
B1181HHHHS(CH2)7CH3CH2
B1182HHHHSO(CH2)7CH3CH2
B1183HHHHSO2(CH2)7CH3CH2
B1184HHHHNHSO2CH3CH2
B1185HHHHNH(CO)S(CH2)7CH3CH2
B1186HHHHClCH2
B1187HHHHNH2CH2
B1188HHHHOC(O)C(CH3)3CH2
B1189HHHHOC(O)CH3CH2
B1190HHHHOC(O)PhCH2
B1191HHHHOC(O)-cyclopropylCH2
B1192HHHHOC(O)CH2CH3CH2
B1193HHHHOC(O)OH═OH2CH2
B1194HHHHOC(O)CH═CHCH3CH2
B1195HHHHOC(O)SCH3CH2
B1196HHHHOC(O)S(CH2)7CH3CH2
B1197HHHHOC(O)OCH2CH3CH2
B1198HHHHOC(O)N(CH2CH3)2CH2
B1199HHHHS-(4-Cl-phenyl)CH2
B1200HHHHSO-(4-Cl-phenyl)CH2
B1201HHHHSO2-(4-Cl-phenyl)CH2
B1202HHHHS-(4-CF3-phenyl)CH2
B1203HHHHSO-(4-CF3-phenyl)CH2
B1204HHHHSO2-(4-CF3-phenyl)CH2
B1205HHHHS-(4-NO2phenyl)CH2
B1206HHHHSO-(4-NO2phenyl)CH2
B1207HHHHSO2-(4-NO2phenyl)CH2
B1208HHHH 96embedded image CH2
B1209HHHH 97embedded image CH2
B1210HHHH 98embedded image CH2
B1211HHHH 99embedded image CH2
B1212HHHH 100embedded image CH2
B1179CH3CH3HHO—K+CH2
B1180CH3CH3HHS(CH2)7CH3CH2
B1181CH3CH3HHSO(CH2)7CH3CH2
B1182CH3CH3HHSO2(CH2)7CH3CH2
B1183CH3CH3HHSO2(CH2)7CH3CH2
B1184CH3CH3HHNHSO2CH3CH2
B1185CH3CH3HHNH(CO)S(CH2)7CH3CH2
B1186CH3CH3HHClCH2
B1187CH3CH3HHNH2CH2
B1188CH3CH3HHOC(O)C(CH3)3CH2
B1189CH3CH3HHOC(O)CH3CH2
B1190CH3CH3HHOC(O)PhCH2
B1191CH3CH3HHOC(O)-cyclopropylCH2
B1192CH3CH3HHOC(O)CH2CH3CH2
B1193CH3CH3HHOC(O)CH═CH2CH2
B1194CH3CH3HHOC(O)CH═CHCH3CH2
B1195CH3CH3HHOC(O)SCH3CH2
B1196CH3CH3HHOC(O)S(CH2)7CH3CH2
B1197CH3CH3HHOC(O)OCH2CH3CH2
B1198CH3CH3HHOC(O)N(CH2CH3)2CH2
B1199CH3CH3HHS-(4-Cl-phenyl)CH2
B1200CH3CH3HHSO-(4-Cl-phenyl)CH2
B1201CH3CH3HHSO2-(4-Cl-Phenyl)CH2
B1202CH3CH3HHS-(4-CF3-Phenyl)CH2
B1203CH3CH3HHSO-(4-CF3-Phenyl)CH2
B1204CH3CH3HHSO2-(4-CF3-Phenyl)CH2
B1205CH3CH3HHS-(4-NO2-Phenyl)CH2
B1206CH3CH3HHSO-(4-NO2-Phenyl)CH2
B1207CH3CH3HHSO2-(4-NO2-Phenyl)CH2
B1208CH3CH3HH 101embedded image CH2
B1209CH3CH3HH 102embedded image CH2
B1210CH3CH3HH 103embedded image CH2
B1211CH3CH3HH 104embedded image CH2
B1212CH3CH3HH 105embedded image CH2
B1213HHHHOH—CH2CH2—
B1214CH3HHHOH—CH2CH2—
B1215CH3CH3HHOH—CH2CH2—
B1216CH3CH3CH3HOH—CH2CH2—
B1217CH3CH3CH3CH3OH—CH2CH2—

[0221] 3

TABLE 3
In Table 3 which follows, Q is Q2
(Q2)
106embedded image
and Q2 the radicals C which follow:
Radicals C:
RadicalR6R7R16R10pW
C1HHHOH1CH2
C2CH3HHOH1CH2
C3CH3CH2HHOH1CH2
C4CH3CH2CH2HHOH1CH2
C5(CH3)2CHHHOH1CH2
C6(CH3)3CHHOH1CH2
C7CH3SHHOH1CH2
C8CH3SOHHOH1CH2
C9CH3SO2HHOH1CH2
C10PhHHOH1CH2
C11CH3OHHOH1CH2
C12CH3OC(O)HHOH1CH2
C13CH3CH2OC(O)HHOH1CH2
C14CH2═CHCH2HHOH1CH2
C15HCCCH2HHOH1CH2
C16CF3HHOH1CH2
C17(CH3)2NSO2HHOH1CH2
C18(CH3)2NHHOH1CH2
C19PhOHHOH1CH2
C20PhSHHOH1CH2
C21PhSOHHOH1CH2
C22PhSO2HHOH1CH2
C23CNHHOH1CH2
C24CH3CH3HOH1CH2
C25CH3CH2CH3HOH1CH2
C26CH3CH2CH2CH3HOH1CH2
C27(CH3)2CHCH3HOH1CH2
C28(CH3)3CCH3HOH1CH2
C29CH3SCH3HOH1CH2
C30CH3SOCH3HOH1CH2
C31CH3SO2CH3HOH1CH2
C32PhCH3HOH1CH2
C33CH3OCH3HOH1CH2
C34CH3OC(O)CH3HOH1CH2
C35CH3CH2OC(O)CH3HOH1CH2
C36CH2═CHCH2CH3HOH1CH2
C37HCCCH2CH3HOH1CH2
C38CF3CH3HOH1CH2
C39(CH3)2NSO2CH3HOH1CH2
C40(CH3)2NCH3HOH1CH2
C41PhOCH3HOH1CH2
C42PhSCH3HOH1CH2
C43PhSOCH3HOH1CH2
C44PhSO2CH3HOH1CH2
C45CNCH3HOH1CH2
C46HHHOH4CH2
C47CH3HHOH4CH2
C48CH3CH2HHOH4CH2
C49CH3CH2CH2HHOH4CH2
C50(CH3)2CHHHOH4CH2
C51(CH3)3CHHOH4CH2
C52CH3SHHOH4CH2
C53CH3SOHHOH4CH2
C54CH3SO2HHOH4CH2
C55PhHHOH4CH2
C56CH3OHHOH4CH2
C57CH3OC(O)HHOH4CH2
C58CH3CH2OC(O)HHOH4CH2
C59CH2═CHCH2HHOH4CH2
C60HCCCH2HHOH4CH2
C61CF3HHOH4CH2
C62(CH3)2NSO2HHOH4CH2
C63(CH3)2NHHOH4CH2
C64PhOHHOH4CH2
C65PhSHHOH4CH2
C66PhSOHHOH4CH2
C67PhSO2HHOH4CH2
C68CNHHOH4CH2
C69CH3CH3HOH4CH2
C70CH3CH2CH3HOH4CH2
C71CH3CH2CH2CH3HOH4CH2
C72(CH3)2CHCH3HOH4CH2
C73(CH3)3CCH3HOH4CH2
C74CH3SCH3HOH4CH2
C75CH3SOCH3HOH4CH2
C76CH3SO2CH3HOH4CH2
C77PhCH3HOH4CH2
C78CH3OCH3HOH4CH2
C79CH3OC(O)CH3HOH4CH2
C80CH3CH2OC(O)CH3HOH4CH2
C81CH2═CHCH2CH3HOH4CH2
C82HCCCH2CH3HOH4CH2
C83CF3CH3HOH4CH2
C84(CH3)2NSO2CH3HOH4CH2
C85(CH3)2NCH3HOH4CH2
C86PhOCH3HOH4CH2
C87PhSCH3HOH4CH2
C88PhSOCH3HOH4CH2
C89PhSO2CH3HOH4CH2
C90CNCH3HOH4CH2
C91HHHOH3CH2
C92CH3HHOH3CH2
C93CH3CH2HHOH3CH2
C94CH3CH2CH2HHOH3CH2
C95(CH3)2CHHHOH3CH2
C96(CH3)3CHHOH3CH2
C97CH3SHHOH3CH2
C98CH3SOHHOH3CH2
C99CH3SO2HHOH3CH2
C100PhHHOH3CH2
C101CH3OHHOH3CH2
C102CH3OC(O)HHOH3CH2
C103CH3CH2OC(O)HHOH3CH2
C104CH2═CHCH2HHOH3CH2
C105HCCCH2HHOH3CH2
C106CF3HHOH3CH2
C107(CH3)2NSO2HHOH3CH2
C108(CH3)2NHHOH3CH2
C109PhOHHOH3CH2
C110PhSHHOH3CH2
C111PhSOHHOH3CH2
C112PhSO2HHOH3CH2
C113CNHHOH3CH2
C114CH3CH3HOH3CH2
C115CH3CH2CH3HOH3CH2
C116CH3CH2CH2CH3HOH3CH2
C117(CH3)2CHCH3HOH3CH2
C118(CH3)3CCH3HOH3CH2
C119CH3SCH3HOH3CH2
C120CH3SOCH3HOH3CH2
C121CH3SO2CH3HOH3CH2
C122PhCH3HOH3CH2
C123CH3OCH3HOH3CH2
C124CH3OC(O)CH3HOH3CH2
C125CH3CH2OC(O)CH3HOH3CH2
C126CH2═CHCH2CH3HOH3CH2
C127HCCCH2CH3HOH3CH2
C128CF3CH3HOH3CH2
C129(CH3)2NSO2CH3HOH3CH2
C130(CH3)2NCH3HOH3CH2
C131PhOCH3HOH3CH2
C132PhSCH3HOH3CH2
C133PhSOCH3HOH3CH2
C134PhSO2CH3HOH3CH2
C135CNCH3HOH3CH2
C136CH3CH2CH3CH2HOH1CH2
C137HHHOH1CH(CH3)
C138CH3HHOH1CH(CH3)
C139CH3CH3HOH1CH(CH3)
C140CH2CH3HHOH1CH(CH3)
C141CH2CH3CH3HOH1CH(CH3)
C142CH3CH2CH3CH2HOH1CH(CH3)
C143HHCH3OH1CH2
C144CH3CH3CH3OH1CH2
C145CH3CH2CH3CH2CH3OH1CH2
C146HHHOH2CH2
C147CH3CH3HOH2CH2
C148CH3CH2CH3CH2HOH2CH2
C149HHHOH5CH2
C150CH3CH3HOH5CH2
C151CH3CH2CH3CH2HOH5CH2
C152CH3HHOH2CH2

[0222] 4

TABLE 4
In Table 4 which follows, Q is Q3
(Q3)
107embedded image
and Q3 the following radicals D:
Radicals D:
RadicalR6R7R8R12R10o
D1HHHHOH2
D2CH3HHHOH2
D3CH3CH2HHHOH2
D4CH3CH2CH2HHHOH2
D5(CH3)2CHHHHOH2
D6(CH3)3CHHHOH2
D7CH3SHHHOH2
D8CH3SOHHHOH2
D9CH3SO2HHHOH2
D10PhHHHOH2
D11CH3OHHHOH2
D12CH2═CHCH2HHHOH2
D13HCCCH2HHHOH2
D14CF3HHHOH2
D15PhOHHHOH2
D16PhSHHHOH2
D17PhSOHHHOH2
D18PhSO2HHHOH2
D19CH3CH3HHOH2
D20CH3CH2CH3HHOH2
D21CH3CH2CH2CH3HHOH2
D22(CH3)2CHCH3HHOH2
D23(CH3)3CCH3HHOH2
D24CH3SCH3HHOH2
D25CH3SOCH3HHOH2
D26CH3SO2CH3HHOH2
D27PhCH3HHOH2
D28CH3OCH3HHOH2
D29CH2═CHCH2CH3HHOH2
D30HCCCH2CH3HHOH2
D31CF3CH3HHOH2
D32PhOCH3HHOH2
D33PhSCH3HHOH2
D34PhSOCH3HHOH2
D35PhSO2CH3HHOH2
D36HHHHOH3
D37CH3HHHOH3
D38CH3CH2HHHOH3
D39CH3CH2CH2HHHOH3
D40(CH3)2CHHHHOH3
D41(CH3)3CHHHOH3
D42CH3SHHHOH3
` D43CH3SOHHHOH3
D44CH3SO2HHHOH3
D45PhHHHOH3
D46CH3OHHHOH3
D47CH2═CHCH2HHHOH3
D48HCCCH2HHHOH3
D49CF3HHHOH3
D50PhOHHHOH3
D51PhSHHHOH3
D52PhSOHHHOH3
D53PhSO2HHHOH3
D54CH3CH3HHOH3
D55CH3CH2CH3HHOH3
D56CH3CH2CH2CH3HHOH3
D57(CH3)2CHCH3HHOH3
D58(CH3)3CCH3HHOH3
D59CH3SCH3HHOH3
D60CH3SOCH3HHOH3
D61CH3SO2CH3HHOH3
D62PhCH3HHOH3
D63CH3OCH3HHOH3
D64CH2═CHCH2CH3HHOH3
D65HCCCH2CH3HHOH3
D66CF3CH3HHOH3
D67PhOCH3HHOH3
D68PhSCH3HHOH3
D69PhSOCH3HHOH3
D70PhSO2CH3HHOH3
D71HHHHOH4
D72CH3HHHOH4
D73CH3CH2HHHOH4
D74CH3CH2CH2HHHOH4
D75(CH3)2CHHHHOH4
D76(CH3)3CHHHOH4
D77CH3SHHHOH4
D78CH3SOHHHOH4
D79CH3SO2HHHOH4
D80PhHHHOH4
D81CH3OHHHOH4
D82CH2═CHCH2HHHOH4
D83HCCCH2HHHOH4
D84CF3HHHOH4
D85PhOHHHOH4
D86PhSHHHOH4
D87PhSOHHHOH4
D88PhSO2HHHOH4
D89CH3CH3HHOH4
D90CH3CH2CH3HHOH4
D91CH3CH2CH2CH3HHOH4
D92(CH3)2CHCH3HHOH4
D93(CH3)3CCH3HHOH4
D94CH3SCH3HHOH4
D95CH3SOCH3HHOH4
D96CH3SO2CH3HHOH4
D97PhCH3HHOH4
D98CH3OCH3HHOH4
D99CH2═CHCH2CH3HHOH4
D100HCCCH2CH3HHOH4
D101CF3CH3HHOH4
D102PhOCH3HHOH4
D103PhSCH3HHOH4
D104PhSOCH3HHOH4
D105PhSO2CH3HHOH4
D106HHHCH3OH4
D107HHHCH3OH3
D108HHHHOH1
D109CH3HHHOH1
D110CH3OC(O)CH3HHOH1
D111CH3CH2OC(O)CH3HHOH1
D112CH3OCH3HHOH1
D113CH3SCH3HHOH1
D114CH3SOCH3HHOH1
D115CH3SO2CH3HHOH1
D116CH3CH2HHHOH1
D117CH3OC(O)CH3CH2HHOH1
D118CH3CH2OC(O)CH3CH2HHOH1
D119CH3OCH3CH2HHOH1
D120CH3SCH3CH2HHOH1
D121CH3SOCH3CH2HHOH1
D122CH3SO2CH3CH2HHOH1
D123CH3CH2SCH3HHOH1
D124CH3CH2SOCH3HHOH1
D125CH3CH2SO2CH3HHOH1
D126CH3CH2SCH3CH2HHOH1
D127CH3CH2SOCH3CH2HHOH1
D128CH3CH2SO2CH3CH2HHOH1
D129HHCH3HOH1
D130CH3HCH3HOH1
D131CH3OC(O)CH3CH3HOH1
D132CH3CH2OC(O)CH3CH3HOH1
D133CH3OCH3CH3HOH1
D134CH3SCH3CH3HOH1
D135CH3SOCH3CH3HOH1
D136CH3SO2CH3CH3HOH1
D137HHHCH3OH1
D138CH3HHCH3OH1
D139HHCH3CH3OH1
D140CH3CH2OC(O)CH3HHOH4

[0223] 5

TABLE 5
In Table 5 which follows, Q is Q4
(Q4)
108embedded image
and Q4 the following radicals E:
Radicals E:
RadicalR6R7R10XYWq
E1HHOHSCH2CH22
E2CH3HOHSCH2CH22
E3CH3CH3OHSCH2CH22
E4CH3OC(O)HOHSCH2CH22
E5CH3CH3OC(O)OHSCH2CH22
E6HHOHSOCH2CH22
E7CH3HOHSOCH2CH22
E8CH3CH3OHSOCH2CH22
E9CH3OC(O)HOHSOCH2CH22
E10CH3CH3OC(O)OHSOCH2CH22
E11HHOHSO2CH2CH22
E12CH3HOHSO2CH2CH22
E13CH3CH3OHSO2CH2CH22
E14CH3OC(O)HOHSO2CH2CH22
E15CH3CH3OC(O)OHSO2CH2CH22
E16HHOHCOOCH22
E17CH3HOHCOOCH22
E18CH3CH3OHCOOCH22
E19CH3OC(O)HOHCOOCH22
E20CH3CH3OC(O)OHCOOCH22
E21HHOHCOOCH22
E22CH3HOHCOOCH22
E23CH3CH3OHCOOCH22
E24CH3OC(O)HOHCOOCH22
E25CH3CH3OC(O)OHCOOCH22
E26HHOHCOOCH22
E27CH3HOHCOOCH22
E28CH3CH3OHCOOCH22
E29CH3OC(O)HOHCOOCH22
E30CH3CH3OC(O)OHCOOCH22

[0224] 6

TABLE 6
In Table 6 which follows, Q is Q5
(Q5)
109embedded image
and Q5 the radicals F which follow:
Radicals F:
RadicalR6R7R8R10
F1HHHOH
F2CH3HHOH
F3CH3CH3HOH
F4CH3CH3CH3OH
F5HHCH3OH
F6HCH3CH3OH

[0225] 7

TABLE 7
Compounds of the formula Ia
(Ia)
110embedded image
Comp.
No.R2R3R4R5Q1p
A1HHHCF3B240
A2CH3HHCF3B240
A3CH3CH2HHCF3B240
A4(CH3)2CHHHCF3B240
A5(CH3)3CHHCF3B240
A6cyclopropylHHCF3B240
A7CH3(CH2)2HHCF3B240
A8CH3OCH2HHCF3B240
A9CH3O(CH2)2HHCF3B240
A10PhHHCF3B240
A11PhOHHCF3B240
A12PhSHHCF3B240
A13PhSOHHCF3B240
A14PhSO2HHCF3B240
A15CH3SHHCF3B240
A16CH3SOHHCF3B240
A17CF3HHCF3B240
A18F2CHHHCF3B240
A19HCCHHCF3B240
A20CH3CCHHCF3B240
A21CH2═CHHHCF3B240
A22CH2═CHCH2HHCF3B240
A23CH3SO2N(CH3)HHCF3B240
A24(CH3)2NHHCF3B240
A25(CH3)2NSO2HHCF3B240
A26ClCH2HHCF3B240
A27CH3SCH2HHCF3B240
A28CH3SOCH2HHCF3B240
A29CH3SO2CH2HHCF3B240
A30[1.2.4]-triazol-1-HHCF3B240
ylmethyl
A31CH3CF3HCH3B240
A32CH3CH3HCF3B240
A33HHHCF3CF2B240
A34CH3HHCF3CF2B240
A35CH3CH2HHCF3CF2B240
A36cyclopropylHHCF3CF2B240
A37(CH3)3CHHCF3CF2B240
A38(CH3)2CHHHCF3CF2B240
A39CH3(CH2)2HHCF3CF2B240
A40CH3OCH2HHCF3CF2B240
A41CH3O(CH2)2HHCF3CF2B240
A42PhHHCF3CF2B240
A43PhOHHCF3CF2B240
A44PhSHHCF3CF2B240
A45PhSOHHCF3CF2B240
A46PhSO2HHCF3CF2B240
A47CH3SHHCF3CF2B240
A48CH3SOHHCF3CF2B240
A49CF3HHCF3CF2B240
A50F2CHHHCF3CF2B240
A51HCCHHCF3CF2B240
A52CH3CCHHCF3CF2B240
A53CH2═CHHHCF3CF2B240
A54CH2═CHCH2HHCF3CF2B240
A55CH3SO2N(CH3)HHCF3CF2B240
A56(CH3)2NHHCF3CF2B240
A57(CH3)2NSO2HHCF3CF2B240
A58ClCH2HHCF3CF2B240
A59CH3SCH2HHCF3CF2B240
A60CH3SOCH2HHCF3CF2B240
A61CH3SO2CH2HHCF3CF2B240
A62[1.2.4]-triazol-1-HHCF3CF2B240
ylmethyl
A63HHHCF3CF2CF2B240
A64CH3HHCF3CF2CF2B240
A65CH3CH2HHCF3CF2CF2B240
A66cyclopropylHHCF3CF2CF2B240
A67(CH3)3CHHCF3CF2CF2B240
A68(CH3)2CHHHCF3CF2CF2B240
A69CH3(CH2)2HHCF3CF2CF2B240
A70CH3OCH2HHCF3CF2CF2B240
A71CH3O(CH2)2HHCF3CF2CF2B240
A72PhHHCF3CF2CF2B240
A73PhOHHCF3CF2CF2B240
A74PhSHHCF3CF2CF2B240
A75PhSOHHCF3CF2CF2B240
A76PhSO2HHCF3CF2CF2B240
A77CH3SHHCF3CF2CF2B240
A78CH3SOHHCF3CF2CF2B240
A79CF3HHCF3CF2CF2B240
A80F2CHHHCF3CF2CF2B240
A81HCCHHCF3CF2CF2B240
A82CH3CCHHCF3CF2CF2B240
A83CH2═CHHHCF3CF2CF2B240
A84CH2═CHCH2HHCF3CF2CF2B240
A85CH3SO2N(CH3)HHCF3CF2CF2B240
A86(CH3)2NHHCF3CF2CF2B240
A87(CH3)2NSO2HHCF3CF2CF2B240
A88ClCH2HHCF3CF2CF2B240
A89CH3SCH2HHCF3CF2CF2B240
A90CH3SOCH2HHCF3CF2CF2B240
A91CH3SO2CH2HHCF3CF2CF2B240
A92[1.2.4]-triazol-1-HHCF3CF2CF2B240
ylmethyl
A93HHHCF2ClB240
A94CH3HHCF2ClB240
A95CH3CH2HHCF2ClB240
A96cyclopropylHHCF2ClB240
A97(CH3)3CHHCF2ClB240
A98(CH3)2CHHHCF2ClB240
A99CH3(CH2)2HHCF2ClB240
A100CH3OCH2HHCF2ClB240
A101CH3O(CH2)2HHCF2ClB240
A102PhHHCF2ClB240
A103PhOHHCF2ClB240
A104PhSHHCF2ClB240
A105PhSOHHCF2ClB240
A106PhSO2HHCF2ClB240
A107CH3SHHCF2ClB240
A108CH3SOHHCF2ClB240
A109CF3HHCF2ClB240
A110F2CHHHCF2ClB240
A111HCCHHCF2ClB240
A112CH3CCHHCF2ClB240
A113CH2═CHHHCF2ClB240
A114CH2═CHCH2HHCF2ClB240
A115CH3SO2N(CH3)HHCF2ClB240
A116(CH3)2NHHCF2ClB240
A117(CH3)2NSO2HHCF2ClB240
A118ClCH2HHCF2ClB240
A119CH3SCH2HHCF2ClB240
A120CH3SOCH2HHCF2ClB240
A121CH3SO2CH2HHCF2ClB240
A122[1.2.4]-triazol-1-HHCF2ClB240
ylmethyl
A123HHHCHF2B240
A124CH3HHCHF2B240
A125CH3CH2HHCHF2B240
A126cyclopropylHHCHF2B240
A127(CH3)3CHHCHF2B240
A128(CH3)2CHHHCHF2B240
A129CH3(CH2)2HHCHF2B240
A130CH3OCH2HHCHF2B240
A131CH3O(CH2)2HHCHF2B240
A132PhHHCHF2B240
A133PhOHHCHF2B240
A134PhSHHCHF2B240
A135PhSOHHCHF2B240
A136PhSO2HHCHF2B240
A137CH3SHHCHF2B240
A138CH3SOHHCHF2B240
A139CF3HHCHF2B240
A140F2CHHHCHF2B240
A141HCCHHCHF2B240
A142CH3CCHHCHF2B240
A143CH2═CHHHCHF2B240
A144CH2═CHCH2HHCHF2B240
A145CH3SO2N(CH3)HHCHF2B240
A146(CH3)2NHHCHF2B240
A147(CH3)2NSO2HHCHF2B240
A148ClCH2HHCHF2B240
A149CH3SCH2HHCHF2B240
A150CH3SOCH2HHCHF2B240
A151CH3SO2CH2HHCHF2B240
A152[1.2.4]-triazol-1-HHCHF2B240
ylmethyl
A153HHHCCl3B240
A154CH3HHCCl3B240
A155CH3CH2HHCCl3B240
A156cyclopropylHHCCl3B240
A157(CH3)3CHHCCl3B240
A158(CH3)2CHHHCCl3B240
A159CH3(CH2)2HHCCl3B240
A160CH3OCH2HHCCl3B240
A161CH3O(CH2)2HHCCl3B240
A162PhHHCCl3B240
A163PhOHHCCl3B240
A164PhSHHCCl3B240
A165PhSOHHCCl3B240
A166PhSO2HHCCl3B240
A167CH3SHHCCl3B240
A168CH3SOHHCCl3B240
A169CF3HHCCl3B240
A170F2CHHHCCl3B240
A171HCCHHCCl3B240
A172CH3CCHHCCl3B240
A173CH2═CHHHCCl3B240
A174CH2═CHCH2HHCCl3B240
A175CH3SO2N(CH3)HHCCl3B240
A176(CH3)2NHHCCl3B240
A177(CH3)2NSO2HHCCl3B240
A178ClCH2HHCCl3B240
A179CH3SCH2HHCCl3B240
A180CH3SOCH2HHCCl3B240
A181CH3SO2CH2HHCCl3B240
A182[1.2.4]-triazol-1-HHCCl3B240
ylmethyl
A183HHCH3CF3B240
A184CH3HCH3CF3B240
A185CH3CH2HCH3CF3B240
A186cyclopropylHCH3CF3B240
A187(CH3)3CHCH3CF3B240
A188(CH3)2CHHCH3CF3B240
A189CH3(CH2)2HCH3CF3B240
A190CH3OCH2HCH3CF3B240
A191CH3O(CH2)2HCH3CF3B240
A192PhHCH3CF3B240
A193PhOHCH3CF3B240
A194PhSHCH3CF3B240
A195PhSOHCH3CF3B240
A196PhSO2HCH3CF3B240
A197CH3SHCH3CF3B240
A198CH3SOHCH3CF3B240
A199CF3HCH3CF3B240
A200F2CHHCH3CF3B240
A201HCCHCH3CF3B240
A202CH3CCHCH3CF3B240
A203CH2═CHHCH3CF3B240
A204CH2═CHCH2HCH3CF3B240
A205CH3SO2N(CH3)HCH3CF3B240
A206(CH3)2NHCH3CF3B240
A207(CH3)2NSO2HCH3CF3B240
A208ClCH2HCH3CF3B240
A209CH3SCH2HCH3CF3B240
A210CH3SOCH2HCH3CF3B240
A211CH3SO2CH2HCH3CF3B240
A212HHCH3CF3CF2B240
A213CH3HCH3CF3CF2B240
A214CH3CH2HCH3CF3CF2B240
A215cyclopropylHCH3CF3CF2B240
A216(CH3)3CHCH3CF3CF2B240
A217(CH3)2CHHCH3CF3CF2B240
A218CH3(CH2)2HCH3CF3CF2B240
A219CH3OCH2HCH3CF3CF2B240
A220CH3O(CH2)2HCH3CF3CF2B240
A221PhHCH3CF3CF2B240
A222PhOHCH3CF3CF2B240
A223PhSHCH3CF3CF2B240
A224PhSOHCH3CF3CF2B240
A225PhSO2HCH3CF3CF2B240
A226CH3SHCH3CF3CF2B240
A227CH3SOHCH3CF3CF2B240
A228CF3HCH3CF3CF2B240
A229F2CHHCH3CF3CF2B240
A230HCCHCH3CF3CF2B240
A231CH3CCHCH3CF3CF2B240
A232CH2═CHHCH3CF3CF2B240
A233CH2═CHCH2HCH3CF3CF2B240
A234CH3SO2N(CH3)HCH3CF3CF2B240
A235(CH3)2NHCH3CF3CF2B240
A236(CH3)2NSO2HCH3CF3CF2B240
A237ClCH2HCH3CF3CF2B240
A238CH3SCH2HCH3CF3CF2B240
A239CH3SOCH2HCH3CF3CF2B240
A240CH3SO2CH2HCH3CF3CF2B240
A241HHCH3CF3CF2CF2B240
A242CH3HCH3CF3CF2CF2B240
A243CH3CH2HCH3CF3CF2CF2B240
A244cyclopropylHCH3CF3CF2CF2B240
A245(CH3)3CHCH3CF3CF2CF2B240
A246(CH3)2CHHCH3CF3CF2CF2B240
A247CH3(CH2)2HCH3CF3CF2CF2B240
A248CH3OCH2HCH3CF3CF2CF2B240
A249CH3O(CH2)2HCH3CF3CF2CF2B240
A250PhHCH3CF3CF2CF2B240
A251PhOHCH3CF3CF2CF2B240
A252PhSHCH3CF3CF2CF2B240
A253PhSOHCH3CF3CF2CF2B240
A254PhSO2HCH3CF3CF2CF2B240
A255CH3SHCH3CF3CF2CF2B240
A256CH3SOHCH3CF3CF2CF2B240
A257CF3HCH3CF3CF2CF2B240
A258F2CHHCH3CF3CF2CF2B240
A259HCCHCH3CF3CF2CF2B240
A260CH3CCHCH3CF3CF2CF2B240
A261CH2═CHHCH3CF3CF2CF2B240
A262CH2CHCH2HCH3CF3CF2CF2B240
A263CH3SO2N(CH3)HCH3CF3CF2CF2B240
A264(CH3)2NHCH3CF3CF2CF2B240
A265(CH3)2NSO2HCH3CF3CF2CF2B240
A266ClCH2HCH3CF3CF2CF2B240
A267CH3SCH2HCH3CF3CF2CF2B240
A268CH3SOCH2HCH3CF3CF2CF2B240
A269CH3SO2CH2HCH3CF3CF2CF2B240
A270HHCH3CF2ClB240
A271CH3HCH3CF2ClB240
A272CH3CH2HCH3CF2ClB240
A273cyclopropylHCH3CF2ClB240
A274(CH3)3CHCH3CF2ClB240
A275(CH3)2CHHCH3CF2ClB240
A276CH3(CH2)2HCH3CF2ClB240
A277CH3OCH2HCH3CF2ClB240
A278CH3O(CH2)2HCH3CF2ClB240
A279PhHCH3CF2ClB240
A280PhOHCH3CF2ClB240
A281PhSHCH3CF2ClB240
A282PhSOHCH3CF2ClB240
A283PhSO2HCH3CF2ClB240
A284CH3SHCH3CF2ClB240
A285CH3SOHCH3CF2ClB240
A286CF3HCH3CF2ClB240
A287F2CHHCH3CF2ClB240
A288HCCHCH3CF2ClB240
A289CH3CCHCH3CF2ClB240
A290CH2═CHHCH3CF2ClB240
A291CH2═CHCH2HCH3CF2ClB240
A292CH3SO2N(CH3)HCH3CF2ClB240
A293(CH3)2NHCH3CF2ClB240
A294(CH3)2NSO2HCH3CF2ClB240
A295ClCH2HCH3CF2ClB240
A296CH3SCH2HCH3CF2ClB240
A297CH3SOCH2HCH3CF2ClB240
A298CH3SO2CH2HCH3CF2ClB240
A299HHCH3CHF2B240
A300CH3HCH3CHF2B240
A301CH3CH2HCH3CHF2B240
A302cyclopropylHCH3CHF2B240
A303(CH3)3CHCH3CHF2B240
A304(CH3)2CHHCH3CHF2B240
A305CH3(CH2)2HCH3CHF2B240
A306CH3OCH2HCH3CHF2B240
A307CH3O(CH2)2HCH3CHF2B240
A308PhHCH3CHF2B240
A309PhOHCH3CHF2B240
A310PhSHCH3CHF2B240
A311PhSOHCH3CHF2B240
A312PhSO2HCH3CHF2B240
A313CH3SHCH3CHF2B240
A314CH3SOHCH3CHF2B240
A315CF3HCH3CHF2B240
A316F2CHHCH3CHF2B240
A317HCCHCH3CHF2B240
A318CH3CCHCH3CHF2B240
A319CH2═CHHCH3CHF2B240
A320CH2═CHCH2HCH3CHF2B240
A321CH3SO2N(CH3)HCH3CHF2B240
A322(CH3)2NHCH3CHF2B240
A323(CH3)2NSO2HCH3CHF2B240
A324ClCH2HCH3CHF2B240
A325CH3SCH2HCH3CHF2B240
A326CH3SOCH2HCH3CHF2B240
A327CH3SO2CH2HCH3CHF2B240
A328HHCH3CCl3B240
A329CH3HCH3CCl3B240
A330CH3CH2HCH3CCl3B240
A331(CH3)3CHCH3CCl3B240
A332(CH3)2CHHCH3CCl3B240
A333cyclopropylHCH3CCl3B240
A334CH3(CH2)2HCH3CCl3B240
A335CH3OCH2HCH3CCl3B240
A336CH3O(CH2)2HCH3CCl3B240
A337PhHCH3CCl3B240
A338PhOHCH3CCl3B240
A339PhSHCH3CCl3B240
A340PhSOHCH3CCl3B240
A341PhSO2HCH3CCl3B240
A342CH3SHCH3CCl3B240
A343CH3SOHCH3CCl3B240
A344CF3HCH3CCl3B240
A345F2CHHCH3CCl3B240
A346HCCHCH3CCl3B240
A347CH3CCHCH3CCl3B240
A348CH2═CHHCH3CCl3B240
A349CH2═CHCH2HCH3CCl3B240
A350CH3SO2N(CH3)HCH3CCl3B240
A351(CH3)2NHCH3CCl3B240
A352(CH3)2NSO2HCH3CCl3B240
A353ClCH2HCH3CCl3B240
A354CH3SCH2HCH3CCl3B240
A355CH3SOCH2HCH3CCl3B240
A356CH3SO2CH2HCH3CCl3B240
A357HHPhCF3B240
A358CH3HPhCF3B240
A359CH3CH2HPhCF3B240
A360cyclopropylHPhCF3B240
A361(CH3)3CHPhCF3B240
A362(CH3)2CHHPhCF3B240
A363CH3(CH2)2HPhCF3B240
A364CH3OCH2HPhCF3B240
A365CH3O(CH2)2HPhCF3B240
A366PhHPhCF3B240
A367PhOHPhCF3B240
A368PhSHPhCF3B240
A369PhSOHPhCF3B240
A370PhSO2HPhCF3B240
A371CH3SHPhCF3B240
A372CH3SOHPhCF3B240
A373CF3HPhCF3B240
A374F2CHHPhCF3B240
A375HCCHPhCF3B240
A376CH3CCHPhCF3B240
A377CH2═CHHPhCF3B240
A378CH2═CHCH2HPhCF3B240
A379CH3SO2N(CH3)HPhCF3B240
A380(CH3)2NHPhCF3B240
A381(CH3)2NSO2HPhCF3B240
A382ClCH2HPhCF3B240
A383CH3SCH2HPhCF3B240
A384CH3SOCH2HPhCF3B240
A385CH3SO2CH2HPhCF3B240
A386HHPhCF3CF2B240
A387CH3HPhCF3CF2B240
A388CH3CH2HPhCF3CF2B240
A389cyclopropylHPhCF3CF2B240
A390(CH3)3CHPhCF3CF2B240
A391(CH3)2CHHPhCF3CF2B240
A392CH3(CH2)2HPhCF3CF2B240
A393CH3OCH2HPhCF3CF2B240
A394CH3O(CH2)2HPhCF3CF2B240
A395PhHPhCF3CF2B240
A396PhOHPhCF3CF2B240
A397PhSHPhCF3CF2B240
A398PhSOHPhCF3CF2B240
A399PhSO2HPhCF3CF2B240
A400CH3SHPhCF3CF2B240
A401CH3SOHPhCF3CF2B240
A402CF3HPhCF3CF2B240
A403F2CHHPhCF3CF2B240
A404HCCHPhCF3CF2B240
A405CH3CCHPhCF3CF2B240
A406CH2═CHHPhCF3CF2B240
A407CH2═CHCH2HPhCF3CF2B240
A408CH3SO2N(CH3)HPhCF3CF2B240
A409(CH3)2NHPhCF3CF2B240
A410(CH3)2NSO2HPhCF3CF2B240
A411ClCH2HPhCF3CF2B240
A412CH3SCH2HPhCF3CF2B240
A413CH3SOCH2HPhCF3CF2B240
A414CH3SO2CH2HPhCF3CF2B240
A415HHPhCF3CF2CF2B240
A416CH3HPhCF3CF2CF2B240
A417CH3CH2HPhCF3CF2CF2B240
A418cyclopropylHPhCF3CF2CF2B240
A419(CH3)3CHPhCF3CF2CF2B240
A420(CH3)2CHHPhCF3CF2CF2B240
A421CH3(CH2)2HPhCF3CF2CF2B240
A422CH3OCH2HPhCF3CF2CF2B240
A423CH3O(CH2)2HPhCF3CF2CF2B240
A424PhHPhCF3CF2CF2B240
A425PhOHPhCF3CF2CF2B240
A426PhSHPhCF3CF2CF2B240
A427PhSOHPhCF3CF2CF2B240
A428PhSO2HPhCF3CF2CF2B240
A429CH3SHPhCF3CF2CF2B240
A430CH3SOHPhCF3CF2CF2B240
A431CF3HPhCF3CF2CF2B240
A432F2CHHPhCF3CF2CF2B240
A433HCCHPhCF3CF2CF2B240
A434CH3CCHPhCF3CF2CF2B240
A435CH2═CHHPhCF3CF2CF2B240
A436CH2═CHCH2HPhCF3CF2CF2B240
A437CH3SO2N(CH3)HPhCF3CF2CF2B240
A438(CH3)2NHPhCF3CF2CF2B240
A439(CH3)2NSO2HPhCF3CF2CF2B240
A440ClCH2HPhCF3CF2CF2B240
A441CH3SCH2HPhCF3CF2CF2B240
A442CH3SOCH2HPhCF3CF2CF2B240
A443CH3SO2CH2HPhCF3CF2CF2B240
A444HHPhCF2ClB240
A445CH3HPhCF2ClB240
A446CH3CH2HPhCF2ClB240
A447cyclopropylHPhCF2ClB240
A448(CH3)3CHPhCF2ClB240
A449(CH3)2CHHPhCF2ClB240
A450CH3(CH2)2HPhCF2ClB240
A451CH3OCH2HPhCF2ClB240
A452CH3O(CH2)2HPhCF2ClB240
A453PhHPhCF2ClB240
A454PhOHPhCF2ClB240
A455PhSHPhCF2ClB240
A456PhSOHPhCF2ClB240
A457PhSO2HPhCF2ClB240
A458CH3SHPhCF2ClB240
A459CH3SOHPhCF2ClB240
A460CF3HPhCF2ClB240
A461F2CHHPhCF2ClB240
A462HCCHPhCF2ClB240
A463CH3CCHPhCF2ClB240
A464CH2═CHHPhCF2ClB240
A465CH2═CHCH2HPhCF2ClB240
A466CH3SO2N(CH3)HPhCF2ClB240
A467(CH3)2NHPhCF2ClB240
A468(CH3)2NSO2HPhCF2ClB240
A469ClCH2HPhCF2ClB240
A470CH3SCH2HPhCF2ClB240
A471CH3SOCH2HPhCF2ClB240
A472CH3SO2CH2HPhCF2ClB240
A473HHPhCHF2B240
A474CH3HPhCHF2B240
A475CH3CH2HPhCHF2B240
A476cyclopropylHPhCHF2B240
A477(CH3)3CHPhCHF2B240
A478(CH3)2CHHPhCHF2B240
A479CH3(CH2)2HPhCHF2B240
A480CH3OCH2HPhCHF2B240
A481CH3O(CH2)2HPhCHF2B240
A482PhHPhCHF2B240
A483PhOHPhCHF2B240
A484PhSHPhCHF2B240
A485PhSOHPhCHF2B240
A486PhSO2HPhCHF2B240
A487CH3SHPhCHF2B240
A488CH3SOHPhCHF2B240
A489CF3HPhCHF2B240
A490F2CHHPhCHF2B240
A491HCCHPhCHF2B240
A492CH3CCHPhCHF2B240
A493CH2═CHHPhCHF2B240
A494CH2═CHCH2HPhCHF2B240
A495CH3SO2N(CH3)HPhCHF2B240
A496(CH3)2NHPhCHF2B240
A497(CH3)2NSO2HPhCHF2B240
A498ClCH2HPhCHF2B240
A499CH3SCH2HPhCHF2B240
A500CH3SOCH2HPhCHF2B240
A501CH3SO2CH2HPhCHF2B240
A502HHPhCCl3B240
A503CH3HPhCCl3B240
A504CH3CH2HPhCCl3B240
A505cyclopropylHPhCCl3B240
A506(CH3)3CHPhCCl3B240
A507(CH3)2CHHPhOCl3B240
A508CH3(CH2)2HPhCCl3B240
A509CH3OCH2HPhCCl3B240
A510CH3O(CH2)2HPhCCl3B240
A511PhHPhCCl3B240
A512PhOHPhCCl3B240
A513PhSHPhCCl3B240
A514PhSOHPhCCl3B240
A515PhSO2HPhCCl3B240
A516CH3SHPhCCl3B240
A517CH3SOHPhCCl3B240
A518CF3HPhCCl3B240
A519F2CHHPhCCl3B240
A520HCCHPhCCl3B240
A521CH3CCHPhCCl3B240
A522CH2═CHHPhCCl3B240
A523CH2═CHCH2HPhCCl3B240
A524CH3SO2N(CH3)HPhCCl3B240
A525(CH3)2NHPhCCl3B240
A526(CH3)2NSO2HPhCCl3B240
A527ClCH2HPhCCl3B240
A528CH3SCH2HPhCCl3B240
A529CH3SOCH2HPhCCl3B240
A530CH3SO2CH2HPhCCl3B240
A531HCH3HCF3B240
A532HCH3CH2HCF3B240
A533HcyclopropylHCF3B240
A534H(CH3)3CHHCF3B240
A535H(CH3)2CHHCF3B240
A536HCH3(CH2)2HCF3B240
A537HCH3OCH2HCF3B240
A538HCH3O(CH2)2HCF3B240
A539HPhHCF3B240
A540HPhOHCF3B240
A541HPhSHCF3B240
A542HPhSOHCF3B240
A543HPhSO2HCF3B240
A544HCH3SHCF3B240
A545HCH3SOHCF3B240
A546HCF3HCF3B240
A547HF2CHHCF3B240
A548HHCCHCF3B240
A549HCH3CCHCF3B240
A550HCH2═CHHCF3B240
A551HCH2═CHCH2HCF3B240
A552HCH3SO2N(CH3)HCF3B240
A553H(CH3)2NHCF3B240
A554H(CH3)2NSO2HCF3B240
A555HCH3SCH2HCF3B240
A556HCH3SOCH2HCF3B240
A557HCH3SO2CH2HCF3B2