Herbicidal 1-aryl-Δ2 -1,2,4-triazolin-5-ones and sulfur analogs thereof

Claim 2

An herbicidal compound of the formula ##STR16## in which X 1 and X 2 are independently selected from halogen, haloalkyl and alkyl; W is oxygen; R is alkyl, haloalkyl, cyanoalkyl; R 1 is alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, or a group of the formula --alkyl--Y 1 --R 6 ; R 2 is alkyl, cyanoalkyl, haloalkyl, arylalkyl, or a group of the formula --alkyl--Y 2 --R 7 ; R 6 , R 7 are independently alkyl, alkoxycarbonylalkyl, alkenyl, or alkynyl; and Y 1 , Y 2 are independently oxygen or S(O) r in which r is 0 to 2.

Claim 3

The compound of claim 1 in which X 1 and X 2 are independently selected from halogen, haloalkyl of 1 to 3 carbon atoms, and alkyl of 1 to 5 carbon atoms; R is alkyl of 1 to 8 carbon atoms, haloalkyl, or oganoalkyl wherein each alkyl is of 1 to 5 carbon atoms, R 1 is alkyl or haloalkyl of 1 to 5 carbon atoms, cyanoalkyl of 1 to 3 alkyl carbon atoms, alkenyl or alkynyl of 2 to 5 carbon atoms, or a group (CH 2 ) n --Y 1 --R 6 wherein n is 1 to 5; R 2 is alkyl, haloalkyl, cyanoalkyl, or arylalkyl wherein each alkyl is of 1 to 3 carbon atoms, or a group (CH 2 ) n --Y 2 --R 7 wherein n is 1 to 5; R 6 , R 7 are independently alkyl of 1 to 5 carbon atoms, alkenyl or alkynyl of 2 to 5 carbon atoms or a radical --CH(R 9 )CO 2 R 10 ; R 9 is hydrogen or alkyl of 1 to 4 carbon atoms; R 10 is alkyl of 1 to 4 carbon atoms; and Y 1 , Y 2 are independently oxygen or S(O) r in which r is 0 to 2.

Claim 4

The compound of claim 2 in which R is alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 3 carbon atoms, cyanoalkyl of 1 to 3 alkyl carbon atoms.

Claim 5

The compound of claim 3 in which R is methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, 1-methylpropyl, 3-methylbutyl, chloromethyl, dichloromethyl, 3-chloropropyl, bromomethyl difluoromethyl trifluoromethyl, or cyanomethyl.

Claim 6

The compound of claim 4 in which R is methyl.

Claim 7

The compound of claim 2 in which X 1 and X 2 are the same and are selected from fluorine, chlorine, and bromine, or X 1 and X 2 are different and X 1 is fluorine or chlorine and X 2 is chlorine, bromine, haloalkyl, or alkyl.

Claim 8

The compound of claim 6 in which for X 2 haloalkyl is difluoromethyl and alkyl is methyl.

Claim 9

The compound of claim 7 in which X 1 is fluorine and X 2 is chlorine.

Claim 10

The compound of claim 2 in which R 1 is alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 3 carbon atoms and one or more halogen atoms selected independently from fluorine and chlorine, cyanoalkyl of 1 to 3 alkyl carbon atoms, alkenyl or alkynyl of 3 to 5 carbon atoms, or a group --(CH 2 ) 2 --Y 1 --R 6 in which Y 1 is oxygen or sulfur and R 6 is alkyl of 1 to 5 carbon atoms.

Claim 11

The compound of claim 9 in which R 1 is alkyl of 1 to 3 carbon atoms, fluoroalkyl of 1 to 3 carbon atoms, cyanomethyl, 2-propenyl, 2-propynyl, or a group --(CH 2 ) 2 --Y 1 --R 6 in which R 6 is methyl or ethyl.

Claim 12

The compound of claim 10 in which R 1 is difluoromethyl, 3-fluoropropyl, or 2-propenyl.

Claim 13

The compound of claim 11 in which R 1 is difluoromethyl.

Claim 14

The compound of claim 2 in which R 2 is alkyl of 1 to 3 carbon atoms,, haloalkyl of 1 to 3 carbon atoms, cyanoalkyl of 1 to 3 alkyl carbon atoms, benzyl, or a group --(CH 2 ) n --Y 2 --R 7 in which n is 1 or 2, Y 2 is oxygen or sulfur, and R 7 is alkyl of 1 to 5 carbon atoms.

Claim 15

The compound of claim 13 in which R 2 is methyl, fluoroalkyl of 1 to 3 carbon atoms, cyanomethyl, or a group --(CH 2 ) n --Y 2 --R 7 in which R 7 is methyl or ethyl.

Claim 16

The compound of claim 14 in which R 2 is methyl, fluoromethyl, or difluoromethyl.

Claim 17

The compound of claim 15 in which R 2 is methyl.

Claim 18

The compound of claim 2 in which X 1 and X 2 are the same and are selected from fluorine, chlorine, and bromine, or X 1 and X 2 are different and X 1 is fluorine or chlorine and X 2 is chlorine, bromine, haloalkyl, or alkyl; W is oxygen; R is alkyl of 1 to 8 carbon atoms of 1 to 5 alkyl carbonators or cyanoalkyl, of 1 to 5 alkyl carbon atoms; R 1 is alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 3 carbon atoms and one or more halogen atoms selected independently from fluorine and chlorine, cyanoalkyl of 1 to 3 alkyl carbon atoms, alkenyl or alkynyl of 3 to 5 carbon atoms, or a group --(CH 2 ) 2 --Y 1 --R 6 ; R 2 is alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, cyanoalkyl of 1 to 3 alkyl carbon atoms, benzyl, or a group --(CH 2 ) n --Y 2 --R 7 in which n is 1 or 2; R 6 and R 7 are independently alkyl of 1 to 5 carbon atoms; and Y 1 and Y 2 are independently oxygen or sulfur.

Claim 19

The compound of claim 17 in which W is oxygen; X 1 and X 2 are the same and are selected from fluorine, chlorine, and bromine, or X 1 and X 2 are different and X 1 is fluorine or chlorine and X 2 is chlorine, bromine, difluoromethyl, or methyl; R is alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 3 carbon atoms, cyanoalkyl; R 1 is alkyl of 1 to 3 carbon atoms, fluoroalkyl of 1 to 3 carbon atoms, cyanomethyl, 2-propenyl, 2-propynyl, or a group --(CH 2 ) 2 --Y 1 --R 6 ; R 2 is methyl, fluoroalkyl of 1 to 3 carbon atoms, cyanomethyl, or a group --(CH 2 ) n --Y 2 --R 7 ; and

Claim 20

The compound of claim 19 in which X 1 is fluorine and X 2 is chlorine; R 1 is difluoromethyl, 3-fluoropropyl, or 2-propenyl; and R 2 is methyl, fluoromethyl, or difluoromethyl.

Claim 21

The compound of claim 19 in which R is methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, 1-methylpropyl, 3-methylbutyl, chloromethyl, dichloromethyl, 3-chloropropyl, bromomethyl difluoromethyl trifluoromethyl or, cyanomethyl.

Claim 22

The compound of claim 20 in which R is methyl, R 1 is difluoromethyl, and R 2 is methyl.

Claim 23

An herbicidal composition comprising an herbicidally effective amount of a compound of claim 2 in admixture with an inert suitable carrier.

Claim 24

A method for controlling undesired plant growth which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 22.

Claim 25

The method of claim 23 wherein the locus where control is desired is planted or to be planted with soybeans or corn.

Claim 26

The method of claim 24 wherein the locus where control is desired is planted or to be planted with soybeans.

Claim 27

The compound of claim 18 in which X 1 is fluorine and X 2 is bromine; R 1 is difluoromethyl, 3-fluoropropyl, or 2-propenyl; and R 2 is methyl, fluoromethyl, or difluoromethyl.

Claim 28

The compound of claim 26 in which R is methyl, R 1 is difluoromethyl, and R 2 is methyl.