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Synergistic herbicidal compositions

Synergistic herbicidal activity is displayed by compositions comprising the following two components: (a) a pyrrolidone of the formula STR1 in which X is selected from the group consisting of hydrogen, chlorine and methyl; Y is selected from the group consisting of hydrogen, chlorine and bromine; Z is selected from the group consisting of chlorine and bromine; R1 is selected from the group consisting of hydrogen and C1 -C4 alkyl; R2 is selected from the group consisting of hydrogen, halogen, C1 -C4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R3 is selected from the group consisting of hydrogen, C1 -C4 alkyl, chlorine and trifluoromethyl; and (b) a phosphonic acid of the formula STR2 in which R4 is selected from the group consisting of C1 -C4 alkyl, C1 -C4 haloalkyl, and --CH2 NHCH2 COOH, at a weight ratio of (a) to (b) of from about 0.1:1 to about 20:1.

Synergistic herbicidal compositions

Synergistic herbicidal activity is displayed by composition comprising the following two components: (a) a pyrrolidone of the formula STR1 in which X is selected from the group consisting of hydrogen, chlorine, and methyl; Y is selected from the group consisting of hydrogen, chlorine, and bromine; Z is selected from the group consisting of chlorine and bromine; R1 is selected from the group consisting of hydrogen and C1 -C4 alkyl; R2 is selected from the group consisting of hydrogen, C1 -C4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R3 is selected from the group consisting of hydrogen, C1 -C4 alkyl, chlorine and trifluoromethyl; and (b) a cyclohexenedione of the formula STR2 in which R4 is 1'-(2-hydroxyethylimino)ethyl or acetyl, at a weight ratio of (a) to (b) of from about 0.01:1 to about 10:1.

Synergistic herbicidal compositions

Synergistic herbicidal activity is displayed by compositions comprising the following two components: (a) a pyrrolidone of the formula STR1 in which X is selected from the group consisting of hydrogen, chlorine and methyl; Y is selected from the group consisting of hydrogen, chlorine and bromine; Z is selected from the group consisting of chlorine and bromine; R1 is selected from the group consisting of hydrogen and C1 -C4 alkyl; R2 is selected from the group consisting of hydrogen, halogen, C1 -C4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R3 is selected from the group consisting of hydrogen, C1 -C4 alkyl, chlorine and trifluoromethyl; and (b) a m-ureidophenyl carbamate of the formula STR2 in which R4 is C1 -C4 alkyl; R5 is C1 -C4 alkyl; and R6 is selected from the group consisting of hydrogen and C1 -C4 alkyl, 1t a weight ratio of (a) to (b) of from about 0.1: to about 50:1.

Synergistic herbicidal compositions

Synergistic herbicidal activity is displayed by a composition comprising the following two components: (a) a pyrrolidone of the formula STR1 in which X is selected from the group consisting of hydrogen, chlorine and methyl; Y is selected from the group consisting of hydrogen, chlorine and bromine; Z is selected from the group consisting of chlorine and bromine; R1 is selected from the group consisting of hydrogen and C1 -C4 alkyl; R2 is selected from the group consisting of hydrogen, C1 -C4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfonyl, C1 -C4 alkylsulfinyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R3 is selected from the group consisting of hydrogen, C1 -C4 alkyl, chlorine and trifluoromethyl; and (b) a urea of the formula STR2 in which R4 is selected from the group consisting of phenyl and substituted phenyl, wherein the substituents are selected from the group consisting of p-chlorophenoxy and alkylacetamido; R5 is selected from the group consisting of hydrogen and C1 -C4 alkyl; and R6 is selected from the group consisting of C1 -C4 alkyl and C1 -C4 alkoxy; at a weight ratio of (a) to (b) of from about 0.01:1 to about 20:1.

Synergistic herbicidal compositions

Synergistic herbicidal activity is displayed by a composition comprising the following two components: (a) a pyrrolidone of the formula STR1 in which X is selected from the group consisting of hydrogen, chlorine, and methyl; Y is selected from the group consisting of hydrogen, chlorine, and bromine; Z is selected from the group consisting of chlorine and bromine; R1 is selected from the group consisting of hydrogen and C1 -C4 alkyl; R2 is selected from the group consisting of hydrogen, C1 -C4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfonyl, C1 -C4 alkylsulfinyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R3 is selected from the group consisting of hydrogen, C1 -C4 alkyl, chlorine and trifluoromethyl; and (b) 3-amino-1,2,4-triazole, at a weight ratio of (a) to (b) of from about 0.01:1 to about 20:1.

Process for the preparation of N-substituted halopyrrolidones

A novel process is disclosed herein for the preparation of N-substituted halopyrrolidones of the formula STR1 in which X is selected from the group consisting of hydrogen, chlorine, and methyl; Y is selected from the group consisting of hydrogen, chlorine, and bromine; Z is selected from the group consisting of chlorine and bromine; R1 is selected from the group consisting of hydrogen and C1 -C4 alkyl; and R2 is selected from the group consisting of C1 -C6 alkyl, C3 -C6 alkenyl, C1 -C6 haloalkyl, C3 -C7 cycloalkyl, C4 -C8 cycloalkylalkyl, benzyl, chlorobenzyl, and STR2 in which R3 is selected from the group consisting og hydrogen, C1 -C4 alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyan, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R4 is selected from the group consisting of hydrogen, C1 -C4 alkyl, chlorine, and trifluoromethyl; WHICH COMPRISES THE INTRAMOLECULAR CYCLIZATION OF AN α-HALOGEN-CONTAINING N-2-alkenyl amide at a temperature of from about 60° C to about 200° C in the presence of a catalytic amount of a transition-metal-containing catalyst in which the transition metal is selected from the group consisting of vanadium, molybdenum, ruthenium, silver, and copper.