Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1985-12-12
1988-08-23
Hollrah, Glennon H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 13, 560 25, 71 88, 71 94, 71 95, 71 98, 71103, 71105, 71111, 544182, 558255, 558389, 558417, 548556, C01C 7946
Patent
active
047662336
DESCRIPTION:
BRIEF SUMMARY
The invention described in this application pertains to weed control in agriculture, horticulture, and other fields where there is a desire to control unwanted plant growth. More specifically, the present application describes herbicidal 2-aryl-1,2,4-triazine-3,5(2H,4H)-diones, sulfur analogs thereof, compositions of them, methods of preparing them, and methods for preventing or destroying undesired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is desired. The present compounds may be used to effectively control a variety of both grassy and broadleaf plant species. The present invention is particularly useful in agriculture, as a number of the compounds described herein show a selectivity favorable to soybean, corn, cotton, wheat, rice, or other crops at application levels which prevent the growth of or destroy a variety of weeds.
1,2,4-Triazine-3,5(2H,4H)-diones as a class are generally associated with the pharmaceutical or animal health arts and are commonly referred to therein as 6-azauracils. Such compounds, however, are relatively unknown in the herbicide art. In particular, there does not appear to be any disclosure of 2-aryltriazinediones in the art. Herbicidal activity is disclosed in German Offenlegungsschrift No. 3,016,304 for optionally substituted triazinediones having the formula ##STR1## where R.sup.1 is hydrogen, hydroxymethyl or an ester derivative thereof such as a benzoic acid ester, optionally substituted aminomethyl, optionally halo-substituted 2-tetrahydrofuranyl, 2-(2H,5H)dihydrofuranyl, or 2-tetrahydropyranyl, and R.sup.2 is hydrogen, an optionally substituted aminomethyl, optionally halo-substituted 2-tetrahydrofuranyl, or 2-tetrahydropyranyl, with certain provisos.
European Published Patent Application No. 0 011 693 of 1979 refers to phenyltriazinediones having a --NHSO.sub.2 CF.sub.3 substituent on the phenyl group. The compounds of the present invention do not require such a substituent for their herbicidal effects.
It has now been discovered that 2-aryl-1,2,4-triazine-3,5-(2H,4H)-diones and the corresponding sulfur analogs have herbicidal properties and may be used effectively either preemergently or postemergently for herbicidal purposes.
The herbicidal compounds of this invention have the formula ##STR2## where Ar is an aryl radical, preferably a ring-substituted aryl radical. For instance it may have a benzene ring such as the radical indicated by the following formula ##STR3## wherein X.sup.1 may be for instance hydrogen or halogen, preferably fluorine or chlorine, the halogen atom advantageously being positioned at the C-2 carbon atom of the phenyl ring;
X.sup.2 may be hydrogen, halogen such as fluorine, chlorine, or bromine, alkyl of 1 to 6 (preferably 1 to 4) carbon atoms, particularly methyl, haloalkyl of 1 to 5 carbon atoms, for example, trifluoromethyl, alkoxy of 1 to 6 (preferably 1 to 4 ) carbon atoms, or phenoxy or phenylmethoxy which may be ring substituted with halogen or alkyl or alkoxy of 1 to 4 carbon atoms;
Z may be hydrogen or, preferably, a substituent or group selected from fluorine, chlorine, bromine, iodine, cyano, nitro, amino, alkoxycarbonylamino of 1 to 6 (preferably 1 to 4) alkyl carbon atoms, di(alkylcarbonyl)amino in which each alkyl is of 1 to 6 (preferably 1 to 4) carbon atoms, hydroxysulfonyl, alkyl of 1 to 6 (preferably 1 to 4) carbon atoms, haloalkyl of 1 to 5 carbon atoms, --QR, --CO--R.sup.6, --S(O).sub.m R.sup.8, --Q.sup.2 R.sup.9, --OSO.sub.2 R.sup.10, --NHN.dbd.CR.sup.11 R.sup.12, and --Q--CR.sup.3 R.sup.4 --(CH.sub.2).sub.n --CO--Q.sup.1 --R.sup.5.
For Z=--QR, Q may be O, S, or NR.sup.7 ; R.sup.7 may be hydrogen or alkyl of 1 to 6 (preferably 1 to 4) carbon atoms; and R may be alkyl of 1 to 6 (preferably 1 to 4) carbon atoms, which may be substituted with cycloalkyl of 3 to 7 carbon atoms (for example, methyl, 1-methylethyl, or cyclohexylmethyl), cycloalkyl of 3 to 7 (preferably 5 or 6) carbon atoms which may be substituted with alkyl of 1 to 6 carbon atoms (for example
REFERENCES:
patent: 3206450 (1965-09-01), Kelly
patent: 3632574 (1972-01-01), Yamamoto et al.
patent: 3641098 (1972-02-01), Buchel et al.
patent: 3883527 (1975-07-01), Brennan
patent: 3907543 (1975-09-01), Dickore et al.
Whitely et al., Journal of the Chemical Society, 1927, Pt. 1, pp. 521-528.
Miller et al., I, J. Med. Chem. 1981, 24, 1337-1342.
Miller et al., II, J. Med. Chem. 1979, 22, 1483-1487.
Ertelt H. Robinson
FMC Corporation
Hollrah Glennon H.
Kennedy Robert M.
Owens A.
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