Title:
Control of undesirable vegetation
United States Patent 3235360


Abstract:
The invention comprises compounds of the isomeric formulae: or where R1 is C5-8 cycloalkyl, R2 is hydrogen, bromine, chlorine, methyl, ethyl, hydroxymethyl, methoxymethyl or methoxy and R3 is methyl or ethyl, or R2 and R3 together represent a trimethylene or tetramethylene group, and the sodium, potassium and lithium salts thereof. 3-Cyclohexyl-6-methyluracil and its salts are disclaimed. The compounds of the invention are herbicides (see Division A5). Exemplified methods of producing such compounds are chlorination or bromination of compounds in which R2 is hydrogen to give R2 as Cl or Br; reaction of a urea R1NHCONH2 with an ester R1OCOCHR2COR3, where R1 is C1-6\t alkyl, to give R1NHCONHCR3=CH2COOR1, and heating this under substantially anhydrous conditions in the presence of a base to give the Na, K or Li salt of the uracil, followed by acidification if required; reaction of a compound with R2 as H with formaldehyde to give R2 as hydroxymethyl; reaction of a compound with R2 as chloromethyl with an alkali metal methoxide to give R2 as methoxymethyl; reaction of R1NCO with R3C(NH2)=CHCOOC2H5 followed by ring closure with a base and acidification; and reaction of a uracil as defined with a suitable base to give the Na, K or Li salt. 2-(3-Cyclopentylureido)-1-cyclopentene carboxylic acidmethyl ester is obtained from cyclopentylurea and methyl 2-cyclopentanone-1-carboxylate with H3PO4. Specifications 492,742, 968,662, 968,664, 968,665 and 968,666 also are referred to.ALSO:The invention comprises herbicidal compositions comprising at least one compound of the isomeric formul or where R1 is C5-8 cycloalkyl, R2 is hydrogen, bromine, chlorine, methyl, ethyl, hydroxymethyl, methoxymethyl or methoxy and R3 is methyl or ethyl, or R2 and R3 together represent a trimethylene or tetramethylene group, or a sodium, potassium or lithium salt thereof (see Division C2), associated with a compatible diluent, which may be (i) at least in part a liquid other than an oil, e.g. water; (ii) at least in part an oil (see below); (iii) at least in part a solid; or (iv) a surface-active agent (which may also be present in (i)-(iii)). Compositions consisting of (i.e. with no other ingredients) 3-cyclocohexyl-6-methyluracil or a Na, K or Li salt thereof and water and/or methanol are disclaimed. The invention also comprises a method of controlling the growth of weeds at a locus by applying to the locus a herbicidally effective quantity of at least one uracil as defined above or a Na, K or Li salt thereof, if desired in the form of a composition as defined. An oil is defined as a liquid immiscible with water and soluble in ether, and which boils at not below 125 DEG C. Specified diluents and additives are those referred to in the parent Specification. The compositions may also contain one of the 3-substituted uracils disclosed in Specifications 968,662, 968,665 and 968,666. Specification 492,742 also is referred to.



Inventors:
Soboczenski, Edward J.
Application Number:
US23231162A
Publication Date:
02/15/1966
Filing Date:
10/22/1962
Assignee:
Pont DU.
Primary Class:
Other Classes:
544/225, 544/253
International Classes:
C07D239/22; C07D239/28; C07D239/46; C07D239/54; C07D239/70; C07D239/96; C07D401/04; C07F9/6512
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