Meta-anilide urea compositions and their utility as herbicides

Abstract

Abstract META-ANILIDE UREA COMPOSITIONS HAVE THE FORMULA: 1-(R2-N(-R3)-C(=X)-N(-R1)-),3-(R5-C(=Y)-N(-R4)-),(Z)M- BENZENE 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, NAPTHYL, PHENYL OR SUBSTITUTED-PHENYL, INCLUSIVE, IN WHICH THE SUBSTITUENTS ARE HALOGEN, NITRO, OR LOWER ALKOXY; R4 IS HYDROGEN OR LOWER ALKYL; R2 IS HYDROGEN, ALKYL, ETHYL CYCLOALKYL, LOWER ALKENYL, HALOGENATED LOWER ALKYL, CYCLOALKYL HAVING 3 TO 6 CARBON ATOMS, INCLUSIVE, PINONYL 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 0, THEN R5 IS OTHER THAN METHYL OR ETHYL. THE COMPOUNDS ARE USEFUL AS HERBICIDES AND THEY EXHIBIT BOTH PRE-EMERGENCE 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''-PESTAFLUOROPROPIONAMIDOPHENYL)-3,3-DIMETHYL UREA.

Inventors

• 👤 Eugene G Teach

Bibliographic Details