Meta-anilide urea compositions and their utility as herbicides

Abstract

Abstract Meta-anilide urea compositions have the formula: IN WHICH X and Y are, independently, oxygen and sulfur; R1 is hydrogen or lower alkyl; R2 and R3 are, independently, hydrogen, alkyl, lower alkoxy, haloalkyl, lower alkenyl, cycloalkyl having from 3 to 6 carbon atoms, inclusive, carbalkoxyalkyl, furfuryl, naphthyl, phenyl or substituted-phenyl, inclusive, in which the substituents are halogen, nitro, or lower alkoxy; R4 is hydrogen or lower alkyl; R5 is hydrogen, alkyl, ethyl cycloalkyl, lower alkenyl, halogenated lower alkyl, cycloalkyl having 3 to 6 carbon atoms, inclusive, pinonoyl 2,4-dichlorophenoxymethylene, benzyl, phenyl, or substituted-phenyl in which the substituents are halogen, nitro, lower alkyl, lower alkoxy or trihalomethyl; Z is halogen, lower alkyl, nitro, amino or trifluoromethyl, and m is an integer having a value from 0 to 4, inclusive, provided that when R1, R2, R3 and R4 are each hydrogen, X and Y are each oxygen and m is O, then R5 is other than methyl or ethyl. The compounds are useful as herbicides and they exhibit both preemergence and post-emergence activity. Representative compounds are: 1-(3''isobutyramidophenyl)-3-methyl urea, 1-cyclohexyl-3-(3''propionamidophenyl)urea, 1-butyl-3-(3''-propionamidophenyl) urea, 1-butyl-3-(3''-isobutyramidophenyl)urea, 1-(3''-nitrophenyl)-3-(3''isobutyramidophenyl) urea, 1-N,N-dimethyl-3(pivalamidophenyl)urea, 1-(3''-propionamidophenyl)-3-n-butyl thiourea, and 1-(3''-pentafluoropropionamido phenyl)3,3-dimethyl urea.

Inventors

• 👤 Eugene G Teach

Bibliographic Details