Title:
Substituted benzoylisoxazoles and the use thereof as herbicides
Kind Code:
A1


Abstract:
The invention relates to novel substituted benzoylisoxazoles of the general formula (I), embedded image in which
    • n, A, R1, R2, R3, R4, and Z are defined herein, and to processes for their preparation and to their use as herbicides.



Inventors:
Muller, Klaus-helmut (Dusseldorf, DE)
Lehr, Stefan (Langenfeld, DE)
Schallner, Otto (Monheim, DE)
Schwarz, Hans-georg (Langenfeld, DE)
Wroblowsky, Heinz-jurgen (Langenfeld, DE)
Drewes, Mark Wilhelm (Langenfeld, DE)
Feucht, Dieter (Monheim, DE)
Pontzen, Rolf (Leichlingen, DE)
Wetcholowsky, Ingo (Cond. Estancia Marambaia, BR)
Application Number:
10/954396
Publication Date:
04/14/2005
Filing Date:
09/30/2004
Assignee:
MULLER KLAUS-HELMUT
LEHR STEFAN
SCHALLNER OTTO
SCHWARZ HANS-GEORG
WROBLOWSKY HEINZ-JURGEN
DREWES MARK WILHELM
FEUCHT DIETER
PONTZEN ROLF
WETCHOLOWSKY INGO
Primary Class:
Other Classes:
548/374.1
International Classes:
A01N43/80; A01N43/824; A01N43/90; A01P13/00; C07D209/48; C07D231/12; C07D233/32; C07D239/10; C07D249/12; C07D253/08; C07D261/08; C07D275/06; C07D413/10; C07D487/04; (IPC1-7): A01N43/84; C07D231/12
View Patent Images:
Related US Applications:
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20040142823Adjuvant compositions and pesticidesJuly, 2004Elsik et al.
20090305895Isoflavonoid compounds and use thereofDecember, 2009Mclver et al.
20050042238Process for treating aqueous systemsFebruary, 2005Lipiecki et al.
20060264329SulfonylureasNovember, 2006Waldraff et al.
20080085833Use Of Glycerol As An Anti-Moss And/Or Anti-Lichen AgentApril, 2008Parant
20070011781Male sterility in grasses of the genus LoliumJanuary, 2007Gaue et al.
20100004126SOIL CONDITIONER FOR LAWN EARTH AND METHOD OF MANAGING LAWNGRASS GROWTH USING THE SOIL CONDITIONERJanuary, 2010Miyagawa et al.
20040242697Methods of reducing pests by use of iodoacetic acid, bromoacetic acid, 2-iodoacetamide, or 2-bromoacetamideDecember, 2004Rosskopf et al.
20080269051Fungicidal Active Compound CombinationsOctober, 2008Suty-heinze et al.
20090209424Stable Dispersions of Sulfentrazone in a Continuous Phase of Aqueous Glyphosate SaltAugust, 2009Dominiani Jr. et al.



Primary Examiner:
RAO, DEEPAK R
Attorney, Agent or Firm:
BAYER CROPSCIENCE LP (Indianola, PA, US)
Claims:
1. 1-21. (canceled)

22. A compound of the Formula (IE) embedded image in which n represents the number 0, 1 or 2, A represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms, R1 represents hydrogen, represents optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl having 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, R2 represents hydrogen, cyano, carbamoyl, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or represents optionally halogen-substituted alkylthio, alkylsulphinyl or alkylsulphonyl having 1 to 6 carbon atoms, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups, R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups, and Z represents one of the heterocyclic groupings below embedded image embedded image in which the dotted bond is in each case a single bond or a double bond, and each heterocyclic grouping preferably only carries two substituents of the definition R5 and/or R6, Q represents oxygen or sulphur, R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R5 and R5 are located at a double bond—also together with the adjacent radical R5 represents a benzo grouping, and R6 represents hydrogen, hydroxyl, amino, alkylidenamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents optionally halogen- or C1-C4-alkyl-substituted alkanediyl having 3 to 5 carbon atoms, where the individual radicals R5 and R6—if a plurality of them are attached to the same heterocyclic grouping—can have identical or different meanings within the scope of the above said definition of said radicals.

23. A compound of the Formula (II) embedded image in which n represents the number 0, 1, 2 or 3, A represents alkanediyl (alkylene), R1 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl or cycloalkyl, R2 represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and X represents halogen, excluding ethyl 4-(2-bromo-methyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate.

24. A compound of the Formula (IV) embedded image in which n represents the number 0, 1, 2 or 3, A represents alkanediyl (alkylene), R1 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl or cycloalkyl, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulphur atom, or one SO grouping or one S02 grouping) and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle.

Description:

The invention relates to novel substituted benzoylisoxazoles, to processes for their preparation and to their use as herbicides.

It is already known that certain substituted benzoylisoxazoles have herbicidal properties (cf. EP-A-418 175, EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797, EP-A-609 798, EP-A-636 622, U.S. Pat. No. 5,834,402, U.S. Pat. No. 5,863,865, WO-A-96/26192, WO-A-97/27187, WO-A-97/43270, WO-A-99/03856). However, the activity of these compounds is not entirely satisfactory.

This invention, accordingly, provides the novel compounds of the general formula (I), embedded image
in which

    • n represents the number 0, 1, 2 or 3,
    • A represents a single bond or represents alkanediyl (alkylene),
    • R1 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl or cycloalkyl,
    • R2 represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,
    • R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,
    • R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and
    • Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulphur atom, or one SO grouping or one SO2 grouping) and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl—including in combination with hetero atoms, such as alkoxy—are in each case straight-chain or branched.

    • n preferably represents the number 0, 1 or 2.
    • A preferably represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms.
    • R1 preferably represents hydrogen, represents optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkyl-sulphonyl-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl having 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
    • R2 preferably represents hydrogen, cyano, carbamoyl, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alky, alkylcarbonyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or represents in each case optionally halogen-substituted alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms.
    • R3 preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-carbamoyl, halogen, represents in each case optionally halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups.
    • R4 preferably represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups, and
    • Z preferably represents one of the heterocyclic groupings below embedded image embedded image
      in which the dotted bond is in each case a single bond or a double bond, and each heterocyclic grouping preferably only carries two substituents of the definition R5 and/or R6,
    • Q represents oxygen or sulphur,
    • R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio, alkinylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R5 and R5 are located at a double bond—also together with the adjacent radical R5 represents a benzo grouping, and
    • R6 represents hydrogen, hydroxyl, amino, alkylidenamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents optionally halogen- or C1-C4-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,
    • where the individual radicals R5 and R6—if a plurality of them are attached to the same heterocyclic grouping—can have identical or different meanings within the scope of the above definition.
    • Q preferably represents oxygen (O).
    • R5 preferably represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphihyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R5 and R5 are located at a double bond—together with the adjacent radical R5 also represents a benzo grouping.
    • R6 preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl, propinyl or propenyloxy, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).
    • A particularly preferably represents a single bond, methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).
    • R1 particularly preferably represents hydrogen, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
    • R2 particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl or ethylsulphonyl.
    • R3 particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,-bromine, iodine, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.
    • R4 particularly preferably represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.
    • Z particularly preferably represents the heterocyclic groupings embedded image
      R5 particularly preferably represents hydrogen, hydroxyl, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluoro-n-propyl, fluoro-i-propyl, chloro-n-propyl, chloro-i-propyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, trichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy, fluorodichloroethoxy, methylthio, ethylthio, n- or i-propylthio, fluoroethylthio, chloroethylthio, difluoroethylthio, dichloroethylthio, chlorofluoroethylthio, chlorodifluoroethylthio, fluorodichloroethylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, dimethylamino, propenylthio, butenylthio, propinylthio, butinylthio, cyclopropyl, cyclopropylmethyl, cyclopropylmethoxy, phenyl or phenoxy.
    • R6 particularly preferably represents amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylamino, dimethylamino, cyclopropyl or cyclopropylmethyl, or together with R5 represents propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).
    • A very particularly preferably represents a single bond or represents methylene.
    • R1 very particularly preferably represents hydrogen, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl.
    • R2 very particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
    • R3 very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or dimethylaminosulphonyl.
    • R4 very particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or dimethylaminosulphonyl.
    • A most preferably represents methylene.
    • R1 most preferably represents cyclopropyl.
    • R2 most preferably represents hydrogen, methoxycarbonyl or ethoxycarbonyl.
    • R3 most preferably represents chlorine, bromine, cyano, trifluoromethyl or methylsulphonyl.
    • R4 most preferably represents hydrogen, cyano, chlorine, nitro, methyl, trifluoromethyl, methoxy or methylsulphonyl.

Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.

Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.

Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.

Most preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being most preferred.

Among the meanings given as preferred, particularly preferred, very particularly preferred or most preferred, still greater emphasis is given to the compounds of the general formula (IA) embedded image
in which

    • n, A, Q, R1, R2, R3, R4, R5 and R6 are each as defined above, with very particular emphasis on the compounds of the formula (IA) in which A represents methylene.

Moreover, among the meanings given as being preferred, particularly preferred, very particularly preferred or most particularly preferred, still greater emphasis is given to the compounds of the general formula (IB) embedded image
in which

    • n, A, Q, R1, R2, R3, R4, R5 and R6 are each as defined above.

Furthermore, among the meanings given as being preferred, particularly preferred, very particularly preferred or most preferred, still greater emphasis is given to those compounds of the general formula (IC) embedded image
in which

    • n, A, Q, R1, R2, R3, R4, R5 and R6 are each as defined above.

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.

Examples of compounds of the general formula (I) according to the invention are listed in the groups below.
Group 1 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given in the table below:

R3(position-) (R4)nR5R6
HCF3CH3
FCF3CH3
ClCF3CH3
BrCF3CH3
ICF3CH3
NO2CF3CH3
CNCF3CH3
CH3CF3CH3
OCH3CF3CH3
CF3CF3CH3
OCHF2CF3CH3
OCF3CF3CH3
SO2CH3CF3CH3
HOCH3CH3
FOCH3CH3
ClOCH3CH3
BrOCH3CH3
IOCH3CH3
NO2OCH3CH3
CNOCH3CH3
CH3OCH3CH3
OCH3OCH3CH3
CF3OCH3CH3
OCHF2OCH3CH3
OCF3OCH3CH3
SO2CH3OCH3CH3
HSCH3CH3
FSCH3CH3
ClSCH3CH3
BrSCH3CH3
ISCH3CH3
NO2SCH3CH3
CNSCH3CH3
CH3SCH3CH3
OCH3SCH3CH3
CF3SCH3CH3
OCHF2SCH3CH3
OCF3SCH3CH3
SO2CH3SCH3CH3
HOC2H5CH3
FOC2H5CH3
ClOC2H5CH3
BrOC2H5CH3
IOC2H5CH3
NO2OC2H5CH3
CNOC2H5CH3
CH3OC2H5CH3
OCH3OC2H5CH3
CF3OC2H5CH3
OCHF2OC2H5CH3
OCF3OC2H5CH3
SO2CH3OC2H5CH3
HN(CH3)2CH3
FN(CH3)2CH3
ClN(CH3)2CH3
BrN(CH3)2CH3
IN(CH3)2CH3
NO2N(CH3)2CH3
CNN(CH3)2CH3
CH3N(CH3)2CH3
OCH3N(CH3)2CH3
CF3N(CH3)2CH3
OCHF2N(CH3)2CH3
OCF3N(CH3)2CH3
SO2CH3N(CH3)2CH3
HOCH3 embedded image
FOCH3 embedded image
ClOCH3 embedded image
BrOCH3 embedded image
IOCH3 embedded image
NO2OCH3 embedded image
CNOCH3 embedded image
CH3OCH3 embedded image
OCH3OCH3 embedded image
CF3OCH3 embedded image
OCHF2OCH3 embedded image
OCF3OCH3 embedded image
SO2CH3OCH3 embedded image
H(3-) ClCF3CH3
F(3-) ClCH3CH3
Cl(3-) ClOCH3CH3
Br(3-) ClBr embedded image
Cl(3-) ClCF3Cl3
NO2(3-) ClCH3CH3
Cl(3-) ClSCH3CH3
CH3(3-) ClClCH3
OCH3(3-) ClOCH3CH3
CF3(3-) ClCF3CH3
OCHF2(3-) ClCH3CH3
OCF3(3-) ClCH3CH3
SO2CH3(3-) ClOCH3CH3

Group 2 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for Group 1.
Group 3 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for Group 1.
Group 4 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for Group 1, and m represents the number 0, 1 or 2.
Group 5 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for Group 1.
Group 6 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for Group 1.
Group 7 embedded image
Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for Group 1.
Group 8 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given for group 1, and m represents the number 0, 1 or 2.
Group 9 embedded image

Here, R3, (R4)n, R5 and R6 each have, for example, the meanings given in the table below:

R3(position-) (R4)nR5R6
Cl(2-) ClCF3CH3
Cl(2-) ClSCH3CH3
Cl(2-) ClSC2H5CH3
Cl(2-) ClSC3H7CH3
Cl(2-) ClSC3H7-iCH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) ClSCH═C═CH2CH3
Cl(2-) ClSCH2CNCH3
Cl(2-) ClSCH2CH2CNCH3
Cl(2-) ClOCH3CH3
Cl(2-) ClOC2H5CH3
Cl(2-) ClOC3H7CH3
Cl(2-) ClOC3H7-iCH3
Cl(2-) ClOC4H9CH3
Cl(2-) ClOCH2CF3CH3
Cl(2-) Cl embedded image CH3
Cl(2-) ClOC6H5CH3
Cl(2-) ClHCH3
Cl(2-) ClCH3CH3
Cl(2-) ClC2H5CH3
Cl(2-) ClC3H7CH3
Cl(2-) ClC3H7-iCH3
Cl(2-) ClC4H9CH3
Cl(2-) ClC4H9-iCH3
Cl(2-) ClC4H9-sCH3
Cl(2-) ClC4H9-tCH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) ClCH═CHCH3CH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) Cl embedded image CH3
Cl(2-) ClN(CH3)2CH3
Cl(2-) Cl embedded image CH3
Cl(2-) ClClCH3
Cl(2-) ClBrCH3
SO2CH3(2-) ClCF3CH3
SO2CH3(2-) ClSCH3CH3
SO2CH3(2-) ClSC2H5CH3
SO2CH3(2-) ClSC3H7CH3
SO2CH3(2-) ClSC3H7-iCH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) ClSCH═C═CH2CH3
SO2CH3(2-) ClSCH2CNCH3
SO2CH3(2-) ClSCH2CH2CNCH3
SO2CH3(2-) ClOCH3CH3
SO2CH3(2-) ClOC2H5CH3
SO2CH3(2-) ClOC3H7CH3
SO2CH3(2-) ClOC3H7-iCH3
SO2CH3(2-) ClOC4H9CH3
SO2CH3(2-) ClOCH2CF3CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) ClOC6H5CH3
SO2CH3(2-) ClHCH3
SO2CH3(2-) ClCH3CH3
SO2CH3(2-) ClC2H5CH3
SO2CH3(2-) ClC3H7CH3
SO2CH3(2-) ClC3H7-iCH3
SO2CH3(2-) ClC4H9CH3
SO2CH3(2-) ClC4H9-iCH3
SO2CH3(2-) ClC4H9-sCH3
SO2CH3(2-) ClC4H9-tCH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) ClCH═CHCH3CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) ClN(CH3)2CH3
SO2CH3(2-) Cl embedded image CH3
SO2CH3(2-) ClClCH3
SO2CH3(2-) ClBrCH3
Cl(2-) SO2CH3CF3CH3
Cl(2-) SO2CH3SCH3CH3
Cl(2-) SO2CH3SC2H5CH3
Cl(2-) SO2CH3SC3H7CH3
Cl(2-) SO2CH3SC3H7-iCH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3SCH═C═CH2CH3
Cl(2-) SO2CH3SCH2CNCH3
Cl(2-) SO2CH3SCH2CH2CNCH3
Cl(2-) SO2CH3OCH3CH3
Cl(2-) SO2CH3OC2H5CH3
Cl(2-) SO2CH3OC3H7CH3
Cl(2-) SO2CH3OC3H7-iCH3
Cl(2-) SO2CH3OC4H9CH3
Cl(2-) SO2CH3OCH2CF3CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3OC6H5CH3
Cl(2-) SO2CH3HCH3
Cl(2-) SO2CH3CH3CH3
Cl(2-) SO2CH3C2H5CH3
Cl(2-) SO2CH3C3H7CH3
Cl(2-) SO2CH3C3H7-iCH3
Cl(2-) SO2CH3C4H9CH3
Cl(2-) SO2CH3C4H9-iCH3
Cl(2-) SO2CH3C4H9-sCH3
Cl(2-) SO2CH3C4H9-tCH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3CH═CHCH3CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3N(CH3)2CH3
Cl(2-) SO2CH3 embedded image CH3
Cl(2-) SO2CH3ClCH3
Cl(2-) SO2CH3BrCH3
Cl(2-) ClCF3 embedded image
Cl(2-) ClSCH3 embedded image
Cl(2-) ClSC2H5 embedded image
Cl(2-) ClSC3H7 embedded image
Cl(2-) ClSC3H7-i embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) ClSCH═C═CH2 embedded image
Cl(2-) ClSCH2CN embedded image
Cl(2-) ClSCH2CH2CN embedded image
Cl(2-) ClOCH3 embedded image
Cl(2-) ClOC2H5 embedded image
Cl(2-) ClOC3H7 embedded image
Cl(2-) ClOC3H7-i embedded image
Cl(2-) ClOC4H9 embedded image
Cl(2-) ClOCH2CF3 embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) ClOC6H5 embedded image
Cl(2-) ClH embedded image
Cl(2-) ClCH3 embedded image
Cl(2-) ClC2H5 embedded image
Cl(2-) ClC3H7 embedded image
Cl(2-) ClC3H7-i embedded image
Cl(2-) ClC4H9 embedded image
Cl(2-) ClC4H9-i embedded image
Cl(2-) ClC4H9-s embedded image
Cl(2-) ClC4H9-t embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) ClCH═CHCH3 embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) ClN(CH3)2 embedded image
Cl(2-) Cl embedded image embedded image
Cl(2-) ClCl embedded image
Cl(2-) ClBr embedded image
SO2CH3(2-) ClCF3 embedded image
SO2CH3(2-) ClSCH3 embedded image
SO2CH3(2-) ClSC2H5 embedded image
SO2CH3(2-) ClSC3H7 embedded image
SO2CH3(2-) ClSC3H7-i embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) ClSCH═C═CH2 embedded image
SO2CH3(2-) ClSCH2CN embedded image
SO2CH3(2-) ClSCH2CH2CN embedded image
SO2CH3(2-) ClOCH3 embedded image
SO2CH3(2-) ClOC2H5 embedded image
SO2CH3(2-) ClOC3H7 embedded image
SO2CH3(2-) ClOC3H7-i embedded image
SO2CH3(2-) ClOC4H9 embedded image
SO2CH3(2-) ClOCH2CF3 embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) ClOC6H5 embedded image
SO2CH3(2-) ClH embedded image
SO2CH3(2-) ClCH3 embedded image
SO2CH3(2-) ClC2H5 embedded image
SO2CH3(2-) ClC3H7 embedded image
SO2CH3(2-) ClC3H9-i embedded image
SO2CH3(2-) ClC4H9 embedded image
SO2CH3(2-) ClC4H9-i embedded image
SO2CH3(2-) ClC4H9-s embedded image
SO2CH3(2-) ClC4H9-t embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) ClCH═CHCH3 embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) ClN(CH3)2 embedded image
SO2CH3(2-) Cl embedded image embedded image
SO2CH3(2-) ClCl embedded image
SO2CH3(2-) ClBr embedded image
Cl(2-) SO2CH3CF3 embedded image
Cl(2-) SO2CH3SCH3 embedded image
Cl(2-) SO2CH3SC2H5 embedded image
Cl(2-) SO2CH3SC3H7 embedded image
Cl(2-) SO2CH3SC3H7-i embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3SCH═C═CH2 embedded image
Cl(2-) SO2CH3SCH2CN embedded image
Cl(2-) SO2CH3SCH2CH2CN embedded image
Cl(2-) SO2CH3OCH3 embedded image
Cl(2-) SO2CH3OC2H5 embedded image
Cl(2-) SO2CH3OC3H7 embedded image
Cl(2-) SO2CH3OC3H7-i embedded image
Cl(2-) SO2CH3OC4H9 embedded image
Cl(2-) SO2CH3OCH2CF3 embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3OC6H5 embedded image
Cl(2-) SO2CH3H embedded image
Cl(2-) SO2CH3CH3 embedded image
Cl(2-) SO2CH3C2H5 embedded image
Cl(2-) SO2CH3C3H7 embedded image
Cl(2-) SO2CH3C3H7-i embedded image
Cl(2-) SO2CH3C4H9 embedded image
Cl(2-) SO2CH3C4H9-i embedded image
Cl(2-) SO2CH3C4H9-s embedded image
Cl(2-) SO2CH3C4H9-t embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3CH═CHCH3 embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3N(CH3)2 embedded image
Cl(2-) SO2CH3 embedded image embedded image
Cl(2-) SO2CH3Cl embedded image
Cl(2-) SO2CH3Br embedded image
Cl(2-) ClCF3N(CH3)2
Cl(2-) ClSCH3N(CH3)2
Cl(2-) ClSC2H5N(CH3)2
Cl(2-) ClSC3H7N(CH3)2
Cl(2-) ClSC3H7-iN(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) ClSCH═C═CH2N(CH3)2
Cl(2-) ClSCH2CNN(CH3)2
Cl(2-) ClSCH2CH2CNN(CH3)2
Cl(2-) ClOCH3N(CH3)2
Cl(2-) ClOC2H5N(CH3)2
Cl(2-) ClOC3H7N(CH3)2
Cl(2-) ClOC3H7-iN(CH3)2
Cl(2-) ClOC4H9N(CH3)2
Cl(2-) ClOCH2CF3N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) ClOC6H5N(CH3)2
Cl(2-) ClHN(CH3)2
Cl(2-) ClCH3N(CH3)2
Cl(2-) ClC2H5N(CH3)2
Cl(2-) ClC3H7N(CH3)2
Cl(2-) ClC3H7-iN(CH3)2
Cl(2-) ClC4H9N(CH3)2
Cl(2-) ClC4H9-iN(CH3)2
Cl(2-) ClC4H9-sN(CH3)2
Cl(2-) ClC4H9-tN(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) ClCH═CHCH3N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) ClN(CH3)2N(CH3)2
Cl(2-) Cl embedded image N(CH3)2
Cl(2-) ClClN(CH3)2
Cl(2-) ClBrN(CH3)2
SO2CH3(2-) ClCF3N(CH3)2
SO2CH3(2-) ClSCH3N(CH3)2
SO2CH3(2-) ClSC2H5N(CH3)2
SO2CH3(2-) ClSC3H7N(CH3)2
SO2CH3(2-) ClSC3H7-iN(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) ClSCH═C═CH2N(CH3)2
SO2CH3(2-) ClSCH2CNN(CH3)2
SO2CH3(2-) ClSCH2CH2CNN(CH3)2
SO2CH3(2-) ClOCH3N(CH3)2
SO2CH3(2-) ClOC2H5N(CH3)2
SO2CH3(2-) ClOC3H7N(CH3)2
SO2CH3(2-) ClOC3H7-iN(CH3)2
SO2CH3(2-) ClOC4H9N(CH3)2
SO2CH3(2-) ClOCH2CF3N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) ClOC6H5N(CH3)2
SO2CH3(2-) ClHN(CH3)2
SO2CH3(2-) ClCH3N(CH3)2
SO2CH3(2-) ClC2H5N(CH3)2
SO2CH3(2-) ClC3H7N(CH3)2
SO2CH3(2-) ClC3H7-iN(CH3)2
SO2CH3(2-) ClC4H9N(CH3)2
SO2CH3(2-) ClC4H9-iN(CH3)2
SO2CH3(2-) ClC4H9-sN(CH3)2
SO2CH3(2-) ClC4H9-tN(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) ClCH═CHCH3N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) ClN(CH3)2N(CH3)2
SO2CH3(2-) Cl embedded image N(CH3)2
SO2CH3(2-) ClClN(CH3)2
SO2CH3(2-) ClBrN(CH3)2
Cl(2-) SO2CH3CF3N(CH3)2
Cl(2-) SO2CH3SCH3N(CH3)2
Cl(2-) SO2CH3SC2H5N(CH3)2
Cl(2-) SO2CH3SC3H7N(CH3)2
Cl(2-) SO2CH3SC3H7-iN(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3SCH═C═CH2N(CH3)2
Cl(2-) SO2CH3SCH2CNN(CH3)2
Cl(2-) SO2CH3SCH2CH2CNN(CH3)2
Cl(2-) SO2CH3OCH3N(CH3)2
Cl(2-) SO2CH3OC2H5N(CH3)2
Cl(2-) SO2CH3OC3H7N(CH3)2
Cl(2-) SO2CH3OC3H7-iN(CH3)2
Cl(2-) SO2CH3OC4H9N(CH3)2
Cl(2-) SO2CH3OCH2CF3N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3OC6H5N(CH3)2
Cl(2-) SO2CH3HN(CH3)2
Cl(2-) SO2CH3CH3N(CH3)2
Cl(2-) SO2CH3C2H5N(CH3)2
Cl(2-) SO2CH3C3H7N(CH3)2
Cl(2-) SO2CH3C3H7-iN(CH3)2
Cl(2-) SO2CH3C4H9N(CH3)2
Cl(2-) SO2CH3C4H9-iN(CH3)2
Cl(2-) SO2CH3C4H9-sN(CH3)2
Cl(2-) SO2CH3C4H9-tN(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3CH═CHCH3N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3N(CH3)2N(CH3)2
Cl(2-) SO2CH3 embedded image N(CH3)2
Cl(2-) SO2CH3ClN(CH3)2
Cl(2-) SO2CH3BrN(CH3)2
Cl(2-) ClCH3OCH3
Cl(2-) ClC2H5OCH3
Cl(2-) ClC3H7OCH3
Cl(2-) ClSCH3OCH3
Cl(2-) ClSC2H5OCH3
Cl(2-) ClOCH3OCH3
Cl(2-) ClOC2H5OCH3
Cl(2-) ClCH3OC2H5
Cl(2-) ClC2H5OC2H5
Cl(2-) ClC3H7OC2H5
Cl(2-) ClSCH3OC2H5
Cl(2-) ClSC2H5OC2H5
Cl(2-) ClOCH3OC2H5
Cl(2-) ClOC2H5OC2H5
Cl(2-) SO2CH3CH3OCH3
Cl(2-) SO2CH3C2H5OCH3
Cl(2-) SO2CH3C3H7OCH3
Cl(2-) SO2CH3SCH3OCH3
Cl(2-) SO2CH3SC2H5OCH3
Cl(2-) SO2CH3OCH3OCH3
Cl(2-) SO2CH3OC2H5OCH3
Cl(2-) SO2CH3CH3OC2H5
Cl(2-) SO2CH3C2H5OC2H5
Cl(2-) SO2CH3C3H7OC2H5
Cl(2-) SO2CH3SCH3OC2H5
Cl(2-) SO2CH3SC2H5OC2H5
Cl(2-) SO2CH3OCH3OC2H5
Cl(2-) SO2CH3OC2H5OC2H5
SO2CH3(2-) ClClOCH3
SO2CH3(2-) ClBrOCH3
SO2CH3(2-) ClCH3OCH3
SO2CH3(2-) ClC2H5OCH3
SO2CH3(2-) ClC3H7OCH3
SO2CH3(2-) ClSCH3OCH3
SO2CH3(2-) ClSC2H5OCH3
SO2CH3(2-) ClOCH3OC2H5
SO2CH3(2-) ClOC2H5OC2H5
SO2CH3(2-) ClCH3OC2H5
SO2CH3(2-) ClC2H5OC2H5
SO2CH3(2-) ClC3H7OC2H5
SO2CH3(2-) ClSCH3OC2H5
SO2CH3(2-) ClSC2H5OC2H5
SO2CH3(2-) ClOCH3OC2H5
CF3(2-) ClBrCH3
CF3(2-) ClSCH3CH3
CF3(2-) ClOCH3CH3
CF3(2-) ClN(CH3)2CH3
CF3(2-) ClCF3CH3
CF3(2-) NO2BrCH3
CF3(2-) NO2SCH3CH3
CF3(2-) NO2OCH3CH3
CF3(2-) NO2N(CH3)2CH3
CF3(2-) NO2CF3CH3
CF3(2-) CH3BrCH3
CF3(2-) CH3SCH3CH3
CF3(2-) CH3OCH3CH3
CF3(2-) CH3N(CH3)2CH3
CF3(2-) CH3CF3CH3
CF3(2-) OCH3BrCH3
CF3(2-) OCH3SCH3CH3
CF3(2-) OCH3OCH3CH3
CF3(2-) OCH3N(CH3)2CH3
CF3(2-) OCH3CF3CH3
SO2CH3(2-) NO2BrCH3
SO2CH3(2-) NO2SCH3CH3
SO2CH3(2-) NO2OCH3CH3
SO2CH3(2-) NO2N(CH3)2CH3
SO2CH3(2-) NO2CF3CH3
SO2CH3(2-) CF3BrCH3
SO2CH3(2-) CF3SCH3CH3
SO2CH3(2-) CF3OCH3CH3
SO2CH3(2-) CF3N(CH3)2CH3
SO2CH3(2-) CF3CF3CH3
SO2CH3(2-) SO2CH3BrCH3
SO2CH3(2-) SO2CH3SCH3CH3
SO2CH3(2-) SO2CH3OCH3CH3
SO2CH3(2-) SO2CH3N(CH3)2CH3
SO2CH3(2-) SO2CH3CF3CH3
CN(2-) ClBrCH3
CN(2-) ClSCH3CH3
CN(2-) ClOCH3CH3
CN(2-) ClN(CH3)2CH3
CN(2-) ClCF3CH3
CN(2-) NO2BrCH3
CN(2-) NO2SCH3CH3
CN(2-) NO2OCH3CH3
CN(2-) NO2N(CH3)2CH3
CN(2-) NO2CF3CH3
CN(2-) CF3BrCH3
CN(2-) CF3SCH3CH3
CN(2-) CF3OCH3CH3
CN(2-) CF3N(CH3)2CH3
CN(2-) CF3CF3CH3
CN(2-) SO2CH3BrCH3
CN(2-) SO2CH3SCH3CH3
CN(2-) SO2CH3OCH3CH3
CN(2-) SO2CH3N(CH3)2CH3
CN(2-) SO2CH3CF3CH3
Br(2-) NO2BrCH3
Br(2-) NO2SCH3CH3
Br(2-) NO2OCH3CH3
Br(2-) NO2N(CH3)2CH3
Br(2-) NO2CF3CH3
Br(2-) CF3BrCH3
Br(2-) CF3SCH3CH3
Br(2-) CF3OCH3CH3
Br(2-) CF3N(CH3)2CH3
Br(2-) CF3CF3CH3
Br(2-) SO2CH3BrCH3
Br(2-) SO2CH3SCH3CH3
Br(2-) SO2CH3OCH3CH3
Br(2-) SO2CH3N(CH3)2CH3
Br(2-) SO2CH3CF3CH3
Br(2-) CH3BrCH3
Br(2-) CH3SCH3CH3
Br(2-) CH3OCH3CH3
Br(2-) CH3N(CH3)2CH3
Br(2-) CH3CF3CH3
Cl(2-) OCH3CF3CH3
Cl(2-) OCH3SCH3CH3
Cl(2-) OCH3SC2H5CH3
Cl(2-) OCH3SC3H7CH3
Cl(2-) OCH3SC3H7-iCH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3SCH═C═CH2CH3
Cl(2-) OCH3SCH2CNCH3
Cl(2-) OCH3SCH2CH2CNCH3
Cl(2-) OCH3OCH3CH3
Cl(2-) OCH3OC2H5CH3
Cl(2-) OCH3OC3H7CH3
Cl(2-) OCH3OC3H7-iCH3
Cl(2-) OCH3OC4H9CH3
Cl(2-) OCH3OCH2CF3CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3OC6H5CH3
Cl(2-) OCH3HCH3
Cl(2-) OCH3CH3CH3
Cl(2-) OCH3C2H5CH3
Cl(2-) OCH3C3H7CH3
Cl(2-) OCH3C3H7-iCH3
Cl(2-) OCH3C4H9CH3
Cl(2-) OCH3C4H9-iCH3
Cl(2-) OCH3C4H9-sCH3
Cl(2-) OCH3C4H9-tCH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3CH═CHCH3CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3N(CH3)2CH3
Cl(2-) OCH3 embedded image CH3
Cl(2-) OCH3ClCH3
Cl(2-) OCH3BrCH3
SO2CH3(2-) OCH3CF3CH3
SO2CH3(2-) OCH3SCH3CH3
SO2CH3(2-) OCH3SC2H5CH3
SO2CH3(2-) OCH3SC3H7CH3
SO2CH3(2-) OCH3SC3H7-iCH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3SCH═C═CH2CH3
SO2CH3(2-) OCH3SCH2CNCH3
SO2CH3(2-) OCH3SCH2CH2CNCH3
SO2CH3(2-) OCH3OCH3CH3
SO2CH3(2-) OCH3OC2H5CH3
SO2CH3(2-) OCH3OC3H7CH3
SO2CH3(2-) OCH3OC3H7-iCH3
SO2CH3(2-) OCH3OC4H9CH3
SO2CH3(2-) OCH3OCH2CF3CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3OC6H5CH3
SO2CH3(2-) OCH3HCH3
SO2CH3(2-) OCH3CH3CH3
SO2CH3(2-) OCH3C2H5CH3
SO2CH3(2-) OCH3C3H7CH3
SO2CH3(2-) OCH3C3H7-iCH3
SO2CH3(2-) OCH3C4H9CH3
SO2CH3(2-) OCH3C4H9-iCH3
SO2CH3(2-) OCH3C4H9-sCH3
SO2CH3(2-) OCH3C4H9-tCH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3CH═CHCH3CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3N(CH3)2CH3
SO2CH3(2-) OCH3 embedded image CH3
SO2CH3(2-) OCH3ClCH3
SO2CH3(2-) OCH3BrCH3
Cl(2-) OCH3CF3 embedded image
Cl(2-) OCH3SCH3 embedded image
Cl(2-) OCH3SC2H5 embedded image
Cl(2-) OCH3SC3H7 embedded image
Cl(2-) OCH3SC3H7-i embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3SCH═C═CH2 embedded image
Cl(2-) OCH3SCH2CN embedded image
Cl(2-) OCH3SCH2CH2CN embedded image
Cl(2-) OCH3OCH3 embedded image
Cl(2-) OCH3OC2H5 embedded image
Cl(2-) OCH3OC3H7 embedded image
Cl(2-) OCH3OC3H7-i embedded image
Cl(2-) OCH3OC4H9 embedded image
Cl(2-) OCH3OCH2CF3 embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3OC6H5 embedded image
Cl(2-) OCH3H embedded image
Cl(2-) OCH3CH3 embedded image
Cl(2-) OCH3C2H5 embedded image
Cl(2-) OCH3C3H7 embedded image
Cl(2-) OCH3C3H7-i embedded image
Cl(2-) OCH3C4H9 embedded image
Cl(2-) OCH3C4H9-i embedded image
Cl(2-) OCH3C4H9-s embedded image
Cl(2-) OCH3C4H9-t embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3CH═CHCH3 embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3N(CH3)2 embedded image
Cl(2-) OCH3 embedded image embedded image
Cl(2-) OCH3Cl embedded image
Cl(2-) OCH3Br embedded image
SO2CH3(2-) OCH3CF3 embedded image
SO2CH3(2-) OCH3SCH3 embedded image
SO2CH3(2-) OCH3SC2H5 embedded image
SO2CH3(2-) OCH3SC3H7 embedded image
SO2CH3(2-) OCH3SC3H7-i embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3SCH═C═CH2 embedded image
SO2CH3(2-) OCH3SCH2CN embedded image
SO2CH3(2-) OCH3SCH2CH2CN embedded image
SO2CH3(2-) OCH3OCH3 embedded image
SO2CH3(2-) OCH3OC2H5 embedded image
SO2CH3(2-) OCH3OC3H7 embedded image
SO2CH3(2-) OCH3OC3H7-i embedded image
SO2CH3(2-) OCH3OC4H9 embedded image
SO2CH3(2-) OCH3OCH2CF3 embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3OC6H5 embedded image
SO2CH3(2-) OCH3H embedded image
SO2CH3(2-) OCH3CH3 embedded image
SO2CH3(2-) OCH3C2H5 embedded image
SO2CH3(2-) OCH3C3H7 embedded image
SO2CH3(2-) OCH3C3H7-i embedded image
SO2CH3(2-) OCH3C4H9 embedded image
SO2CH3(2-) OCH3C4H9-i embedded image
SO2CH3(2-) OCH3C4H9-s embedded image
SO2CH3(2-) OCH3C4H9-t embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3CH═CHCH3 embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3N(CH3)2 embedded image
SO2CH3(2-) OCH3 embedded image embedded image
SO2CH3(2-) OCH3Cl embedded image
SO2CH3(2-) OCH3Br embedded image
Cl(2-) OCH3CF3N(CH3)2
Cl(2-) OCH3SCH3N(CH3)2
Cl(2-) OCH3SC2H5N(CH3)2
Cl(2-) OCH3SC3H7N(CH3)2
Cl(2-) OCH3SC3H7-iN(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3SCH═C═CH2N(CH3)2
Cl(2-) OCH3SCH2CNN(CH3)2
Cl(2-) OCH3SCH2CH2CNN(CH3)2
Cl(2-) OCH3OCH3N(CH3)2
Cl(2-) OCH3OC2H5N(CH3)2
Cl(2-) OCH3OC3H7N(CH3)2
Cl(2-) OCH3OC3H7-iN(CH3)2
Cl(2-) OCH3OC4H9N(CH3)2
Cl(2-) OCH3OCH2CF3N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3OC6H5N(CH3)2
Cl(2-) OCH3HN(CH3)2
Cl(2-) OCH3CH3N(CH3)2
Cl(2-) OCH3C2H5N(CH3)2
Cl(2-) OCH3C3H7N(CH3)2
Cl(2-) OCH3C3H7-iN(CH3)2
Cl(2-) OCH3C4H9N(CH3)2
Cl(2-) OCH3C4H9-iN(CH3)2
Cl(2-) OCH3C4H9-sN(CH3)2
Cl(2-) OCH3C4H9-tN(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3CH═CHCH3N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3N(CH3)2N(CH3)2
Cl(2-) OCH3 embedded image N(CH3)2
Cl(2-) OCH3ClN(CH3)2
Cl(2-) OCH3BrN(CH3)2
SO2CH3(2-) OCH3CF3N(CH3)2
SO2CH3(2-) OCH3SCH3N(CH3)2
SO2CH3(2-) OCH3SC2H5N(CH3)2
SO2CH3(2-) OCH3SC3H7N(CH3)2
SO2CH3(2-) OCH3SC3H7-iN(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3SCH═C═CH2N(CH3)2
SO2CH3(2-) OCH3SCH2CNN(CH3)2
SO2CH3(2-) OCH3SCH2CH2CNN(CH3)2
SO2CH3(2-) OCH3OCH3N(CH3)2
SO2CH3(2-) OCH3OC2H5N(CH3)2
SO2CH3(2-) OCH3OC3H7N(CH3)2
SO2CH3(2-) OCH3OC3H7-iN(CH3)2
SO2CH3(2-) OCH3OC4H9N(CH3)2
SO2CH3(2-) OCH3OCH2CF3N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3OC6H5N(CH3)2
SO2CH3(2-) OCH3HN(CH3)2
SO2CH3(2-) OCH3CH3N(CH3)2
SO2CH3(2-) OCH3C2H5N(CH3)2
SO2CH3(2-) OCH3C3H7N(CH3)2
SO2CH3(2-) OCH3C3H7-iN(CH3)2
SO2CH3(2-) OCH3C4H9N(CH3)2
SO2CH3(2-) OCH3C4H9-iN(CH3)2
SO2CH3(2-) OCH3C4H9-sN(CH3)2
SO2CH3(2-) OCH3C4H9-tN(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3CH═CHCH3N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3N(CH3)2N(CH3)2
SO2CH3(2-) OCH3 embedded image N(CH3)2
SO2CH3(2-) OCH3ClN(CH3)2
SO2CH3(2-) OCH3BrN(CH3)2
Cl(2-) OCH3CH3OCH3
Cl(2-) OCH3C2H5OCH3
Cl(2-) OCH3C3H7OCH3
Cl(2-) OCH3SCH3OCH3
Cl(2-) OCH3SC2H5OCH3
Cl(2-) OCH3OCH3OCH3
Cl(2-) OCH3OC2H5OCH3
Cl(2-) OCH3CH3OC2H5
Cl(2-) OCH3C2H5OC2H5
Cl(2-) OCH3C3H7OC2H5
Cl(2-) OCH3SCH3OC2H5
Cl(2-) OCH3SC2H5OC2H5
Cl(2-) OCH3OCH3OC2H5
Cl(2-) OCH3OC2H5OC2H5
SO2CH3(2-) OCH3ClOCH3
SO2CH3(2-) OCH3BrOCH3
SO2CH3(2-) OCH3CH3OCH3
SO2CH3(2-) OCH3C2H5OCH3
SO2CH3(2-) OCH3C3H7OCH3
SO2CH3(2-) OCH3SCH3OCH3
SO2CH3(2-) OCH3SC2H5OCH3
SO2CH3(2-) OCH3OCH3OC2H5
SO2CH3(2-) OCH3OC2H5OC2H5
SO2CH3(2-) OCH3CH3OC2H5
SO2CH3(2-) OCH3C2H5OC2H5
SO2CH3(2-) OCH3C3H7OC2H5
SO2CH3(2-) OCH3SCH3OC2H5
SO2CH3(2-) OCH3SC2H5OC2H5
SO2CH3(2-) OCH3OCH3OC2H5

Group 10 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9.
Group 11 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9.
Group 12 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9, and m represents the number 0, 1 or 2.
Group 13 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9.
Group 14 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9.
Group 15 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9.
Group 16 embedded image

Here, R3, (R4)n, R5 and R6 have, for example, the meanings given for Group 9, and m represents the number 0, 1 or 2.

The novel substituted benzoylisoxazoles of the general formula (I) have strong and selective herbicidal activity.

The novel substituted benzoylisoxazoles of the general formula (I) are obtained when

    • (a) benzoylisoxazoles of the general formula (II) embedded image
      in which
    • n, A, R1, R2, R3 and R4 are each as defined above and
    • X represents halogen
    • are reacted with heterocycles of the general formula (III)
      H-Z (III)
      in which
    • Z is as defined above,
    • if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
    • or when
    • if R2 is hydrogen
    • (b) benzoyl ketones of the general formula (IV) embedded image
      in which
    • n, A, R1, R3, R4 and Z are each as defined above
    • are reacted with a trialkyl orthoformate or an N,N-dimethylformamide dialkyl acetal and subsequently with hydroxylamine or an acid adduct thereof,
    • if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
    • or when
    • if R2 represents optionally substituted alkoxycarbonyl
    • (c) benzoyl ketones of the general formula (IV) embedded image
      in which
    • n, A, R1, R3, R4 and Z are each as defined above are reacted with an alkyl cyanoformate and then with hydroxylamine or an acid adduct thereof, or with an alkyl chloro-hydroximino-acetate, if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
    • or when
    • if R2 represents alkylthio
    • (d) benzoyl ketones of the general formula (IV) embedded image
      in which
    • n, A, R1, R3, R4 and Z are each as defined above
    • are reacted with carbon disulphide and with an alkylating agent and then with hydroxylamine or an acid adduct thereof,
    • if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
    • and electrophilic or nucleophilic substitutions and/or oxidations or reductions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner on the compounds of the formula (I) obtained according to processes (a) to (d).

The compounds of the formula (I) can be converted by customary methods into other compounds of the formula (I) according to the above definition, for example by nucleophilic substitution (for example R5:Cl→OC2H5, SCH3) or by oxidation (for example R5:CH2SCH3→CH2S(O)CH3).

In the preparation of compounds of the general formula (I), it is also possible that compounds of the general formula (IE) embedded image
in which

    • n, A, R1, R2, R3, R4 and Z are each as defined above
    • are formed in certain amounts.

The compounds of the general formula (IE) also form, as novel substances, part of the subject-matter of the present application.

Using, for example, (3-chloromethyl-4-trifluoromethyl-phenyl)-(3,5-dimethyl-iso-xazol-4-yl)-methanone and 4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme: embedded image

Using, for example, 1-[2-chloro-3-(3,4-dimethyl-5-oxo-4,5-dihydro-[1,2,4-triazol-1-yl-methyl)-phenyl]-pentane-1,3-dione, N,N-dimethyl-formamide diethyl acetal and hydroxylamine as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme: embedded image

Using, for example, 1-[2-chloro-3-(4-ethoxy-3-ethyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-methyl)-phenyl]-3-cyclopropyl-propane1,3-dione, ethyl cyanoformate and hydroxylamine as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme: embedded image

Using, for example, 1-[2-chloro-3-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-methyl)-phenyl]-3-cyclopropyl-propane-1,3-dione, carbon disulphide, methyl bromide and hydroxylamine as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following formula scheme: embedded image

The formula (II) provides a general definition of the benzoylisoxazoles to be used as starting materials in the process (a) according to the invention for preparing compounds of the general formula (I). In the general formula (II), n, A, R1, R2, R3 and R4 each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for n, A, R1, R2, R3 and R4; X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.

Except for ethyl 4-(2-bromo-methyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate (cf WO-A-95/31446), the starting materials of the general formula (II) have hitherto not been disclosed in the literature; except for ethyl 4-(2-bromomethyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate, they also form, as novel substances, part of the subject-matter of the present application.

The novel benzoylisoxazoles of the general formula (II) are obtained when benzoylisoxazoles of the general formula (V) embedded image
in which

    • n, A, R1, R2, R3 and R4 are each as defined above
    • are reacted with a side-chain halogenating agent, such as, for example, N-bromo-succinimide or N-chloro-succinimide, under UV light or in the presence of a reaction auxiliary, such as, for example, 2,2′-azo-bis-isobutyonitrile, in the presence of a diluent, such as, for example, carbon tetrachloride, at temperatures between 0° C. and 100° C. (cf. WO-A-95/31446; Preparation Examples).

The intermediates of the general formula (V) are known and/or can be prepared by processes known per se (cf. WO-A-95/31446; Preparation Examples).

The formula (III) provides a general definition of the heterocycles further to be used as starting materials in the process (a) according to the invention for preparing compounds of the general formula (I). In the general formula (III), Z preferably has that meaning which has already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred for Z.

The starting materials of the general formula (III) are known and/or can be prepared by processes known per se.

The formula (IV) provides a general defintion of the benzoyl ketones to be used as starting materials in the processes (b), (c) and (d) according to the invention for preparing compounds of the general formula (I). In the general formula (IV), n, A, R1, R3, R4 and Z each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for n, A, R1, R3, R4 and Z.

The starting materials of the general formula (IV) have hitherto not been disclosed in the literature; they also, as novel substances, form part of the subject-matter of the present application.

The novel benzoyl ketones of the general formula (IV) are obtained when ketones of the general formula (VI) embedded image
in which

    • R1 is as defined above,
    • are reacted with benzoic acid derivatives of the general formula (VII) embedded image
      in which
    • n, A, R3, R4 and Z are each as defined above, and
    • Y represents halogen (in particular fluorine, chlorine or bromine) or represents optionally substituted alkoxy (in particular methoxy, ethoxy or ethoxyethoxy),
    • if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride, and if appropriate in the presence of a diluent, such as, for example, tetra-hydrofuran, at temperatures between 0° C. and 100° C. (cf. the Preparation Examples).

The benzoic acid derivatives of the general formula (VII) required as intermediates are known and/or can be prepared by processes known per se (cf. DE-A-38 39 480, DE-A-42 39 296, EP-A-597 360, EP-A-609 734, DE-A-43 03 676, EP-A-617 026, DE-A-44 05 614, U.S. Pat. No. 5,378,681).

The benzoic acid derivatives of the general formula (VII) are obtained when halogeno(alkyl)benzoic acid derivatives of the general formula (VIII) embedded image
in which

    • n, A, R3 and R4 are each as defined above and
    • X represents halogen (in particular fluorine, chlorine or bromine) and
    • Y1 represents optionally substituted alkoxy (in particular methoxy, ethoxy or ethoxyethoxy),
    • are reacted with compounds of the general formula (III),
      H-Z (III)
      in which
    • Z is as defined above,
    • if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride, triethylamine or potassium carbonate, and if appropriate in the presence of a diluent, such as, for example, acetone, acetonitrile, N,N-dimethylformamide or N,N-dimethyl-acetamide, at temperatures between 50° C. and 200° C. (cf. the Preparation Examples).

The halogeno(alkyl)benzoic acid derivatives of the formula (VIII) required as intermediates are known and/or can be prepared by processes known per se (cf. EP-A-90 369, EP-A-93 488, EP-A-399 732, EP-A-480 641, EP-A-609 798, EP-A-763 524, DE-A-21 26 720, WO-A-93/03722, WO-A-97/38977, U.S. Pat. No. 3,978,127, U.S. Pat. No. 4,837,333).

The process (b) according to the invention for preparing the compounds of the formula (I) is carried out using orthoformic esters or N,N-dimethylformamide acetals. These compounds preferably contain alkyl groups having 1 to 4 carbon atoms, in particular methyl or ethyl. Examples which may be mentioned are trimethyl orthoformate, triethyl orthoformate, N,N-dimethyl-formamide dimethyl acetal and N,N-dimethyl-formamide diethyl acetal.

The process (c) according to the invention for preparing the compounds of the formula (I) is carried out using alkyl cyanoformates or alkyl chloro-hydroximino-acetates. These compounds preferably contain alkyl groups having 1 to 4 carbon atoms, in particular methyl or ethyl. Examples which may be mentioned are methyl cyanoformate, ethyl cyanoformate, methyl chloro-hydroximino-acetate and ethyl chloro-hydroximino-acetate.

The process (d) according to the invention for preparing the compounds of the formula (I) is carried out using (carbon disulphide and) alkylating agents. These compounds preferably contain alkyl groups having 1 to 4 carbon atoms, in particular methyl or ethyl. Examples which may be mentioned are methyl chloride, methyl bromide, methyl iodide, dimethyl sulphate, ethyl chloride, ethyl bromide, ethyl iodine and diethyl sulphate.

The processes (b), (c) and—if appropriate—(d) according to the invention for preparing the compounds of the formula (I) are carried out using hydroxylamine or an acid adduct thereof. A preferred acid adduct which may be mentioned is hydroxylamine hydrochloride.

The processes according to the invention for preparing the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are, in addition to water, especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.

Suitable reaction auxiliaries for the processes (a), (b), (c) and (d) according to the invention are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hyride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or -t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine tributylaamine ethyl-diisopropylamine N,N-dimethyl-cyclohexylamine, dicyclohexylamine ethyl-dicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine, 4-di-methylamino-pyridine, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

When carrying out the processes (a), (b), (c) and (d) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.

The processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.

For carrying out the processes according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible for one of the components to be used in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

    • Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
    • Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoca, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
    • Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
    • Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

Depending on the concentration, the compounds according to the invention are suitable for total weed control, for example on industrial terrain and rail tracks and on paths and areas with or without tree growth. Equally, the compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops.

The compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent they are also suitable for selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl-formamide and dimethyl sulphoxide, and water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, aryl-sulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.

It is possible to use dyestuffs, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac-(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxy-fen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorosulfuron, chlorotoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop-(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, di-methenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulffiron, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron-(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-animonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop-(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, meto-bromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxazi-clomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), procarbazone, prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazo-sulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tio-carbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin, triflusulfuron and tritosulfuron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to the invention can be seen from the examples below.

PREPARATION EXAMPLES

Example 1

embedded image
(Process (a))

At room temperature (about 20° C.), a solution of 1.20 g (33% pure, i.e. 2.8 mMol) of methyl 4-(3-bromomethyl-5-trifluoromethyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate in 10 ml of N,N-dimethyl-formamide is added dropwise with stirring to a mixture of 0.44 g (2.8 mMol) of 4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 84 mg (2.8 mMol) of sodium hydride (75% pure) and 20 ml of N,N-dimethyl-formamide, and the reaction mixture is stirred at room temperature for 30 minutes. The mixture is then diluted with saturated aqueous sodium chloride solution to about twice its original volume and extracted twice with ethyl acetate. The combined organic extract solutions are dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum and the residue is purified by column chromatography (silica gel, hexane/ethyl acetate, vol.: 7/3).

This gives 0.45 g (96% of theory based on 33% pure starting material) of (5-cyclo-propyl-3-methoxycarbonyl-isoxazol-4-yl)-[2-(4-ethoxy-3-ethyl-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-4-trifluoromethyl-pheny l]-methanone as an amorphous product.

logP (determined at pH=2.3): 3.56.

Example 2

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(process (b))

A mixture of 1.5 g (36 mMol) of 1-cyclopropyl-3-[2-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)4trifluoromethyl-phenyl]-propane-1,3-dione, 0.56 g (46 mMol) of N,N-dimethyl-formamide dimethyl acetal and 15 ml of toluene is stirred at 90° C. for 60 minutes. The mixture is then concentrated under water pump vacuum, the residue is taken up in 15 ml of ethanol and the mixture is, after addition of 0.25 g (36 mMol) of hydroxylamine hydrochloride, stirred at room temperature (about. 20° C.) for two hours. The mixture is concentrated under water pump vacuum, the residue is shaken with methylene chloride/water and the organic phase is separated off, washed with saturated aqueous sodium chloride solution, dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum and the residue is purified by column chromatography (silica gel, ethyl acetate/hexane, vol: 1/1).

This gives 0.20 g (13% of theory) of (5-cyclopropyl-isoxazol-4-yl)-[2-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-4-trifluoromethyl-phenyl]-methanone as an amorphous product.

logP (determined at pH=2.3): 2.94.

Analogously to Examples 1 and 2, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (I)—or of the formulae (IA), (IB), (IC) or (ID)—listed in Tables 1 and 1a below. embedded image

TABLE 1a
Examples of the compounds of the formula (I) or (ID)
Ex.-(position)(position)(position)
No.R1R2R3(R4)n-A-Zphysical data
ID-1 embedded image H(2) Cl(4) Cl embedded image logP = 2.48a)
ID-2 embedded image H(2) OCH3(4) Cl embedded image logP = 2.46a)
ID-3 embedded image H(2) Cl(4) embedded image
ID-4 embedded image H(2) OCH3(4) Cl embedded image
ID-5 embedded image H(2) Cl(4) Cl embedded image
ID-6 embedded image H(2) Cl(4) Cl embedded image
ID-7 embedded image H(2) Cl(4) Cl embedded image
ID-8 embedded image H(2) Cl(4) Cl embedded image
ID-9 embedded image H(2) Cl(4) Cl embedded image
ID-10 embedded image H(2) OCH3(4) Cl embedded image
ID-11 embedded image H(2) Cl(4) SO2CH3 embedded image
ID-12 embedded image H(2) Cl(4) SO2CH3 embedded image
ID-13 embedded image H(2) SO2CH3(4) Cl embedded image
ID-14 embedded image H(2) SO2CH3(4) Cl embedded image
ID-15 embedded image H(2) Cl(4) CF3 embedded image
ID-16 embedded image H(2) Cl(4) CF3 embedded image
ID-17 embedded image H(2) NO2(4) CF3 embedded image
ID-18 embedded image H(2) NO2(4) CF3 embedded image
ID-19 embedded image H (2) OCH3(4) CF3 embedded image
ID-20 embedded image H(2) OCH3(4) CF3 embedded image
ID-21 embedded image H(2) Cl(4) CN embedded image
ID-22 embedded image H(2) Cl(4) CN embedded image
ID-23 embedded image H(2) OCH3(4) CN embedded image
ID-24 embedded image H(2) OCH3(4) CN embedded image
ID-25 embedded image H(2) Cl(4) F embedded image
ID-26 embedded image H(2) Cl(4) F embedded image
ID-27 embedded image HH embedded image
ID-28 embedded image HH embedded image
ID-29 embedded image H(4) F embedded image
ID-30 embedded image H(4) F embedded image
ID-31 embedded image H(4) Cl embedded image
ID-32 embedded image H(4) Cl embedded image
ID-33 embedded image H(4) F embedded image
ID-34 embedded image H(4) Cl embedded image
ID-35 embedded image H(4) Br embedded image
ID-36 embedded image H(4) I embedded image
ID-37 embedded image H(4) NO2 embedded image
ID-38 embedded image H(4) CN embedded image
ID-39 embedded image H(4) CF3 embedded image
ID-40 embedded image H(4) SO2CH3 embedded image
ID-41 embedded image H(4) OCH3 embedded image
ID-42 embedded image H(4) OCF3 embedded image
ID-43 embedded image H(4) OCHF2 embedded image
ID-44 embedded image H(4) SCH3 embedded image
ID-45 embedded image H(4) SOCH3 embedded image
ID-46 embedded image embedded image (2) Cl(4) Cl embedded image
ID-47 embedded image embedded image (2) OCH3(4) Cl embedded image
ID-48 embedded image embedded image (2) Cl(4) Cl embedded image
ID-49 embedded image embedded image (2) OCH3(4) Cl embedded image
ID-50 embedded image SCH3(2) Cl(4) Cl embedded image
ID-51 embedded image SCH3(2) OCH3(4) Cl embedded image
ID-52 embedded image SCH3(2) Cl(4) Cl embedded image
ID-53 embedded image SCH3(2) OCH3(4) Cl embedded image
ID-54 embedded image H(2) Cl(4) Cl embedded image
ID-55 embedded image H(2) OCH3(4) Cl embedded image
ID-56 embedded image H(2) Cl(4) Cl embedded image
ID-57 embedded image H(2) OCH3(4) Cl embedded image
ID-58 embedded image H(4) CF3 embedded image
ID-59 embedded image H(4) CF3 embedded image
ID-60 embedded image H(4) CF3 embedded image
ID-61 embedded image H(2) Cl(4) Cl embedded image
ID-62 embedded image H(2) OCH3(4) Cl embedded image
ID-63 embedded image H(2) Cl(4) Cl embedded image
ID-64 embedded image H(2) OCH3(4) Cl embedded image
ID-65 embedded image H(2) Cl(4) Cl embedded image
ID-66 embedded image H(2) OCH3(4) Cl embedded image
ID-67 embedded image H(2) NO2(4) SO2CH3 embedded image
ID-68 embedded image H(2) NO2(4) SO2CH3 embedded image
ID-69 embedded image H(2) Cl(4) SO2CH3 embedded image
ID-70 embedded image H(2) NO2(4) SO2CH3 embedded image
ID-71 embedded image H(2) NO2(4) CF3 embedded image
ID-72 embedded image H(2) NO2(4) CF3 embedded image
ID-73 embedded image H(2) NO2(4) CF3 embedded image
ID-74 embedded image H(2) Cl(4) SO2CH3 embedded image
ID-75 embedded image H(2) NO2(4) SO2CH3 embedded image
ID-76 embedded image H(2) NO2(4) CF3 embedded image
ID-77 embedded image H(2) Cl(4) SO2CH3 embedded image
ID-78 embedded image H(2) NO2(4) SO2CH3 embedded image
ID-79 embedded image H(2) NO2(4) CF3 embedded image

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reverse-phase column (C 18). Temperature: 43° C.

(a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 1 are labelled a).

(b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 1 are labelled b).

Calibration was carried out using unbranched alkan-2-ones (with from 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

The lambda-max values were determined in the maxima of the chromatographic signals, using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (II)

Example (II-1)

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A mixture of 3.0 g (8.5 Mol) of methyl 5-cyclopropyl-4-(2-methyl-4-trifluoro-methyl-benzoyl)-isoxazole-4-carboxylate, 1.5 g (8.5 mMol) of N-bromo-succinimide, 0.15 g of 2,2′-azo-bis-isobutyronitrile and 45 ml of carbon tetrachloride is heated under reflux for two hours and, after cooling, filtered. The filtrate is diluted with methylene chloride to about twice its original volume, washed with 20% strength aqueous sodium hydrogen sulphite solution, dried with sodium sulphate and filtered. From the filtrate, the solvent is carefully distilled off under water pump vacuum.

This gives 2.5 g (68% of theory) of methyl 5-cyclopropyl-4-(2-bromomethyl-4-trifluoromethyl-benzoyl)-isoxazole-4-carboxylate as an amorphous product which can be reacted further without any purification.

Analogously to Example (II-1), it is also possible to prepare, for example, the compounds of the formula (II) listed in Table 2 below.

TABLE 2
(II)
embedded image
Examples of the compounds of the formula (II)
Ex.-(position)(position)physical
No.R1R2(position) R3(R4)nA—Xdata
II-2 embedded image embedded image (4) Br(2) CH2Br
II-3 embedded image embedded image (4) Cl(2) CH2Br
II-4 embedded image embedded image (4) CH3(2) CH2Br
II-5 embedded image embedded image (4) CN(2) CH2Br
II-6 embedded image embedded image (4) OCH3(2) CH2Br
II-7 embedded image embedded image (4) SCH3(2) CH2Br
II-8 embedded image embedded image (4) SO2CH3(2) CH2Br
II-9 embedded image embedded image (4) SO2N(CH3)2(2) CH2Br
II-10 embedded image SCH3(4) CF3(2) CH2Br
II-11 embedded image embedded image (4) OCHF2(2) CH2Br
II-12 embedded image embedded image (4) OCF3(2) CH2Br
II-13 embedded image embedded image (4) NO2(2) CH2Br
II-14 embedded image embedded image (4) Cl(2) Cl(3) CH2Br
II-15 embedded image H(4) Cl(2) Cl(3) CH2Br
II-16 embedded image embedded image (4) Cl(2) Cl(3) CH2Br
II-17 embedded image embedded image H(3) CH2Br
II-18 embedded image HH(3) CH2Br
II-19 embedded image H(4) Cl(2) OCH3(3) CH2Br
II-20 embedded image H(4) CH3(3) OCH3(2) CH2Br
II-21 embedded image H(4) CN(3) OCH3(2) CH2Br
II-22 embedded image H(4) SO2CH3(3) CH2OCH3(2) CH2Br
II-23 embedded image H(4) CF3(3) CH2OCH3(2) CH2Br
II-24 embedded image H(4) F(2) Cl(3) CH2Br

Starting Materials of the Formula (IV)

Example (IV-1)

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A mixture of 0.94 g (11 mMol) of cyclopropyl methyl ketone, 0.35 g (11 mMol) of sodium hydride (75% pure) and 15 ml of tetrahydrofiran is stirred at 20° C. for 30 minutes. A solution of 2.0 g (5.5 mMol) of 4-methyl-5-methylthio-2-(2-methoxy-carbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one in 8 ml of tetrahydrofuran is then added dropwise and, after addition of 0.2 g of dibenzo-18-crone-6, the reaction mixture is heated under reflux for 60 minutes. After cooling to room temperature, the mixture is diluted with 100 ml of ethyl acetate, shaken with saturated aqueous ammonium chloride solution, dried with sodium sulphate and filtered through silica gel. From the filtrate, the solvent is carefully distilled off under water pump vacuum.

This gives 1.5 g (66% of theory) of 1-cyclopropyl-3-[4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-phenyl]-propane-1,3-dione as an amorphous product which can be reacted further without purification.

Starting Materials of the Formula (VII)

Example (VII-1)

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10 g (49 mMol) of 2-methyl-4-trifluoromethyl-benzoic acid are dissolved in 150 ml of ethanol and admixed with 1 ml of conc. sulphuric acid. The mixture is heated under reflux for 24 hours and then concentrated, the residue is taken up in methylene chloride and the mixture is extracted with saturated aqueous sodium bicarbonate solution. The methylene chloride phase is dried over sodium sulphate and concentrated under water pump vacuum.

This gives 9 g (80% of theory) of ethyl 2-methyl-4-trifluoromethyl-benzoate as an amorphous residue. embedded image

9 g (39 mMol) of ethyl 2-methyl-4-trifluoromethyl-benzoate are dissolved in 200 ml of carbon tetrachloride and admixed with 7 g (39 nMol) of N-bromo-succinimide and 0.1 g of dibenzoyl peroxide. After 6 hours of heating under reflux, the succinimide which has separated off is filtered off, and the filtrate is concentrated under water pump vacuum.

This gives 12 g of an amorphous residue which, in addition to ethyl 2-bromomethyl-4-trifluoromethyl-benzoate, contains 17% of ethyl 2,2-dibromomethyl-4-trifluoro-methyl-benzoate and 12% of ethyl 2-methyl-4-trifluoromethyl-benzoate. embedded image

4 g of ethyl 2-bromomethyl-4-trifluoromethyl-benzoate (about 70% pure) and 2.28 g (12.8 mMol) of 5-bromo-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 150 ml of acetonitrile and the solution is admixed with 5.3 g (38.4 Mol) of potassium carbonate and heated under reflux with vigorous stirring for 2 hours. The reaction mixture is taken up in water and repeatedly extracted with methylene chloride. The combined methylene chloride phases are dried over sodium sulphate, concentrated under water pump vacuum and chromatographed.

This gives 2 g (38% of theory) of 5-bromo-4-methyl-2-(2-ethoxycarbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one as an amorphous product.

1H-NMR (CDCl3, 8): 5.46 ppm.

Example (VII-2)

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6.7 g (40 Mol) of 4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are initially charged in 150 ml of acetonitrile and stirred with 11 g (80 mMol) of potassium carbonate. The mixture is heated to 50° C., and a solution of 13.1 g (44 mMol) of methyl 3-bromomethyl-2,4-dichloro-benzoate in 20 ml of acetonitrile is then added dropwise with stirring, and the reaction mixture is heated with stirring and at reflux for another 15 hours. The mixture is then concentrated under water pump vacuum and the residue is taken up in methylene chloride, washed with 1N hydrochloric acid, dried with sodium sulphate and filtered. The filtrate is concentrated under reduced pressure, the residue is digested with petroleum ether and the resulting crysalline product is isolated by filtration with suction.

This gives 14.9 g (97% of theory) of 4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-methoxycarbonyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 109° C.

Analogously to the Examples (VII-1) and (VII-2), it is also possible to prepare, for example, the compounds of the general formula (VII) listed in Table 3 below.

TABLE 3
(VII)
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Examples of the compounds of the formula (VII)
Ex.(position)(position)(position)physical
No.R3(R4)n—A—ZYdata
VII-3(2-) Cl(4-) Cl embedded image OCH3m.p.: 229° C. logP = 2.27a
VII-4(2-) Cl(4-) Cl embedded image OCH3m.p.: 120° C. logP = 2.38a
VII-5(2-) Cl(4-) Cl embedded image OCH3m.p.: 127° C. logP = 2.55a
VII-6(2-) Cl(4-) Cl embedded image OCH3m.p.: 121° C. logP = 2.04a
VII-7(2-) Cl(4-) Cl embedded image OCH3m.p.: 68° C. logP = 2.73a
VII-8(2-) Cl(4-) Cl embedded image OCH3m.p.: 129° C. logP = 2.72a
VII-9(2-) Cl(4-) Cl embedded image OCH3m.p.: 164° C. logP = 2.18a
VII-10(2-) Cl(4-) Cl embedded image OCH3m.p.: 158° C. logP = 1.55a
VII-11(2-) Cl(4-) Cl embedded image OCH3m.p.: 106° C. logP = 2.16a
VII-12(2-) Cl(4-) Cl embedded image OCH3m.p.: 126° C. logP = 2.11a
VII-13(2-) Cl(4-) Cl embedded image OCH3m.p.: 146° C. logP = 1.65a
VII-14(2-) Cl(4-) Cl embedded image OCH3m.p.: 178° C. logP = 1.86a
VII-15(2-) Cl(4-) Cl embedded image OCH3m.p.: 97° C. logP = 2.36a
VII-16(2-) Cl(4-) Cl embedded image OCH3m.p.: 99° C. logP = 2.73a
VII-17(2-) Cl(4-) Cl embedded image OCH3m.p.: 56° C. logP = 3.08a
VII-18(2-) Cl(4-) Cl embedded image OCH3m.p.: 102° C. logP = 3.05a
VII-19(2-) Cl(4-) Cl embedded image OCH3m.p.: 131° C. logP = 2.70a
VII-20(2-) Cl(4-) Cl embedded image OCH3m.p.: 135° C. logP = 1.97a
VII-21(2-) Cl(4-) Cl embedded image OCH3m.p.: 143° C. logP = 2.42a
VII-22(2-) Cl(4-) Cl embedded image OCH3m.p.: 85° C. logP = 2.58a
VII-23(2-) Cl(4-) Cl embedded image OCH3logP = 1.98a
VII-24(2-) Cl(4-) Cl embedded image OCH3logP = 2.07a
VII-25(2-) Cl(4-) Cl embedded image OCH3m.p.: 157° C. logP = 2.94a
VII-26(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.53 ppm.
VII-27(4-) NO2 embedded image OC2H51H-NMR (CDCl3, δ): 5.48 ppm.
VII-28(4-) NO2 embedded image OC2H51H-NMR (CDCl3, δ): 5.30 ppm.
VII-29(4-) SO2CH3 embedded image OC2H51H-NMR (CDCl3, δ): 5.61 ppm.
VII-30(4-) Cl embedded image OC2H51H-NMR (CDCl3, δ): 5.08 ppm.
VII-31(4-) Cl embedded image OC2H51H-NMR (CDCl3, δ): 5.17 ppm.
VII-32(4-) Cl embedded image OC2H51H-NMR (CDCl3, δ): 5.00 ppm
VII-33(4-) SO2CH3 embedded image OC2H5logP = 1.53a
VII-34(4-) Br embedded image OC2H5logP = 3.24a
VII-35(4-) Br embedded image OC2H5logP = 3.40a
VH-36(4-) F embedded image OC2H5logP = 2.41a
VII-37(4-) F embedded image OC2H5logP = 2.45a
VII-38(4-) Br embedded image OC2H5logP = 2.06a
VII-39(4-) Br embedded image OC2H5logP = 2.64a
VII-40(4-) Br embedded image OC2H5logP = 3.23a
VII-41(4-) Br embedded image OC2H5logP = 3.02a
VII-42(4-) Cl embedded image OC2H5logP = 3.23a
VII-43(4-) Cl embedded image OC2H5logP = 3.31a
VII-44(4-) Cl embedded image OC2H5logP = 3.14a
VII-45(4-) NO2 embedded image OC2H5logP = 2.42a
VII-46(4-) NO2 embedded image OC2H5logP = 2.82a
VII-47(4-) CF3 embedded image OC2H5logP = 3.48a
VII-48(4-) CF3 embedded image OC2H5logP = 3.38a
VII-49(4-) CF3 embedded image OC2H5logP = 3.02a
VII-50(4-) CF3 embedded image OC3H7logP = 3.91a
VII-51(4-) OCH3 embedded image OC2H5
VII-52(4-) OCH3 embedded image OC2H5
VII-53(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.37 ppm.
VII-54(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.37 ppm.
VII-55 embedded image OC2H5
VII-56 embedded image OC2H51H-NMR (CDCl3, δ): 5.37 ppm.
VII-57 embedded image OC2H51H-NMR (CDCl3, δ): 5.40 ppm.
VII-58(4-) Br embedded image OC2H5logP = 2.95a
VII-59(4-) Br embedded image OC2H51H-NMR (CDCl3, δ): 5.31 ppm.
VII-60(4-) Br embedded image OC2H5logP = 2.44a
VII-61(4-) F embedded image OC2H51H-NMR (CDCl3, δ): 5.35 ppm.
VII-62(4-) F embedded image OC2H51H-NMR (CDCl3, δ): 5.53 ppm.
VII-63(4-) F embedded image OC2H51H-NMR (CDCl3, δ): 5.40 ppm.
VII-64(4-) F embedded image OC2H51H-NMR (CDCl3, δ): 5.36 ppm.
VII-65(4-) Br embedded image OC2H5logP = 3.34a
VII-66(4-) Br embedded image OC2H5logP = 3.38a
VII-67(4-) Br embedded image OC2H5logP = 3.31a
VII-68(4-) Br embedded image OC2H5logP = 2.16a
VII-69(4-) Br embedded image OC2H5logP = 2.41a
VII-70(4-) CF3 embedded image OC2H5logP = 3.51a
VII-71(4-) CF3 embedded image OC2H5logP = 3.54a
VII-72(4-) Br embedded image OC2H5logP = 2.36a
VII-73(4-) Br embedded image OC2H5logP = 2.88a
VII-74(4-) CF3 embedded image OC2H5logP = 2.68a
VII-75(4-) Br embedded image OC2H5logP = 2.80a
VII-76(4-) CF3 embedded image OC2H5logP = 3.87a
VII-77(4-) CF3 embedded image OC2H5logP = 2.88a
VII-78(4-) CF3 embedded image OC2H5logP = 2.60a
VII-79(4-) CF3 embedded image OC2H5logP = 3.35a
VII-80(4-) Br embedded image OC2H5logP = 2.86a
VII-81(4-) Cl embedded image OC2H5logP = 2.83a
VII-82(4-) Br embedded image OC2H5logP = 2.60a
VII-83(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.36 ppm.
VII-84(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.37 ppm.
VII-85(4-) CF3 embedded image OC2H5logP = 2.792
VII-86(4-) CF3 embedded image OC2H5logP = 3.67a
VII-87(4-) CF3 embedded image OC2H5logP = 3.80a
VII-88(3-) CH3 embedded image OC2H5logP = 2.54a
VII-89(4-) embedded image OC2H5logP = 1.82a
VII-90(4-) CF3 embedded image OC2H5logP = 2.93a
VII-91(4-) CF3 embedded image OC2H5logP = 3.08a
VII-92(4-) CF3 embedded image OC2H5logP = 3.04a
VII-93(4-) CF3 embedded image OC2H5logP = 3.45a
VII-94(4-) F embedded image OC2H5logP = 2.21a
VII-95(4-) F embedded image OC2H5logP = 2.96a
VII-96(4-) F embedded image OC2H5logP = 2.05a
VII-97(4-) F embedded image OC2H5logP = 2.50a
VII-98(4-) F embedded image OC2H5logP = 2.89a
VII-99(4-) CF3 embedded image OC2H5logP = 2.91a
VII-100(4-) Cl embedded image OC2H51H-NMR (CDCl3, δ): 5.39 ppm.
VII-101(4-) Cl embedded image OC2H51H-NMR (CDCl3, δ): 5.50 ppm.
VII-102(4-) Cl embedded image OC2H51H-NMR (CDCl3, δ): 5.49 ppm.
VII-103(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.29 ppm.
VII-104(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.53 ppm.
VII-105(4-) CF3 embedded image OC2H51H-NMR (CDCl3, δ): 5.34 ppm.
VII-106(4-) SO2CH3 embedded image OC2H51H-NMR (CDCl3, δ): 5.39 ppm.
VII-107(4-) SO2CH3 embedded image OC2H51H-NMR (CDCl3, δ): 5.43 ppm.
VH-108(4-) SO2CH3 embedded image OC2H51H-NMR (CDCl3, δ): 5.40 ppm.
VII-109(4-) SO2CH3 embedded image OC2H51H-NMR (CDCl3, δ): 5.38 ppm.
VII-110(4-) Br embedded image OC2H51H-NMR (CDCl3, δ): 5.49 ppm.
VII-111 embedded image OC2H51H-NMR (CDCl3, δ): 5.3 ppm.
VII-112 embedded image OC2H51H-NMR (CDCl3, δ): 5.44 ppm.
VII-113(4-) CF3 embedded image OC2H5logP = 2.58a
VII-114(4-) SO2CH3 embedded image OCH3logP = 1.53a
VII-115(4-) SO2CH3 embedded image OCH3logP = 1.59a
VII-116(4-) I embedded image OCH3logP = 2.68a
VII-117(4-) CF3 embedded image OCH3logP = 2.74a
VII-118(4-) CF3 embedded image OCH3logP = 2.65a
VII-119(4-) CF3 embedded image OC2H5logP = 2.96a
VII-120 embedded image OCH3m.p.: 106° C.
VII-121(4-) CF3 embedded image OCH3logP = 3.37a
VII-122(4-) CF3 embedded image OCH3logP = 3.29a
VII-123(4-) CF3 embedded image OCH3logP = 3.26a
VII-124(4-) Cl(2-) OCH3 embedded image OCH31H-NMR (DMSO-D6, δ): 4.44 ppm.
VII-125(4-) Cl(2-) OCH3 embedded image OCH31H-NMR (DMSO-D6, δ): 4.66 ppm.
VII-126(4-) Cl(2-) OCH3 embedded image OCH31H-NMR (DMSO-D6, δ): 4.95 ppm.

The logP values given in Table 3 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reverse-phase column (C 18). Temperature: 43° C.

(a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 3 are labelled a).

(b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 3 are labelled b).

Calibration was carried out using unbranched alkan-2-ones (with from 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

The lambda-max values were determined in the maxima of the chromatographic signals, using the UV spectra from 200 nm to 400 nm.

Use Examples

Example A

Pre-Emergence Test

Solvent:5 parts by weight of acetone
Emulsifier:1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0% =no effect (like untreated control)
100% =total destruction

In this test, for example, the compounds of preparation examples 3 and 4 exhibit strong action against weeds, whilst being tolerated well by crop plants, such as, for example, maize.

Example B

Post-Emergence Test

Solvent:5 parts by weight of acetone
Emulsifier:1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0% =no effect (like untreated control)
100% =total destruction

In this test, for example, the compounds of Preparation Examples 3 and 4 exhibit very strong activity against weeds, whilst being tolerated well by crop plants, such as, for example, wheat.