Herbicidal sulfonamides

Claim 2

A compound of the formula: ##STR117## wherein R 1 is F, Cl, Br, CF 3 , C 1 -C 3 alkoxy, C 1 -C 3 alkyl, NO 2 , CO 2 R 4 , SO 2 R 5 , SO 2 NR 6 R 7 , SO 2 N(OCH 3 )CH 3 , SO 2 OCH 2 CF 3 , OSO 2 R 5 or CH 2 L; L is SO 2 NR 6 R 7 , OCH 3 , OC 2 H 5 , CO 2 CH 3 or CO 2 C 2 H 5 ; R 2 is H, Cl, Br, F, CF 3 or OCH 3 ; R 4 is C 1 -C 3 alkyl, CH 2 CH═CH 2 , CH 2 CH 2 Cl, or CH 2 CH 2 OCH 3 ; R 5 is C 1 -C 3 alkyl or CF 3 ; R 6 and R 7 are independently C 1 -C 3 alkyl; R 8 is H or CH 3 ; R 9 is H or C 1 -C 3 alkyl; R 3 is ##STR118## W is O or S; X is CH 3 , OCH 3 or Cl; Y is CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; Z is CH or N; X 1 is H, Cl, CH 3 , OCH 3 or OC 2 H 5 ; X 2 is CH 3 , C 2 H 5 , OCH 3 or OC 2 H 5 ; X 3 is CH 3 or OCH 3 ; and Y 1 is CH 3 or OCH 3 ; and their agriculturally suitable salts; provided that: (1) when W is S, then R 8 is H; (2) the total number of carbon atoms of R 6 and R 7 is less than or equal to 4; and (3) when X is Cl, then Z is CH and Y is NH 2 , NHCH 3 , N(CH 3 ) 2 or OCH 3 .

Claim 3

Compounds of claim 1 wherein R 2 is H; R 8 is H; and W is O.

Claim 4

Compounds of claim 2 wherein R 1 is CF 3 , NO 2 , C 1 -C 3 alkoxy, CO 2 R 4 , SO 2 R 5 , SO 2 NR 6 R 7 , SO 2 N(OCH 3 )CH 3 or OSO 2 R 5 ; R 9 is H; X 3 is OCH 3 ; and Y 1 is OCH 3 .

Claim 5

Compounds of claim 3 wherein R 4 is CH 3 or C 2 H 5 ; R 5 is CH 3 or CF 3 ; and R 6 and R 7 are independently CH 3 or C 2 H 5 .

Claim 6

Compounds of claim 4 wherein ##STR119##

Claim 7

Compounds of claim 5 wherein R 1 is CF 3 , NO 2 , CO 2 CH 3 , SO 2 CH 3 , SO 2 N(CH 3 ) 2 , SO 2 N(OCH 3 )CH 3 or OSO 2 CH 3 .

Claim 8

Compounds of claim 6 wherein X and Y are independently CH 3 or OCH 3 .

Claim 9

The compound of claim 1, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulfonamide.

Claim 10

The compound of claim 1, N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulfonamide.

Claim 11

The compound of claim 1, N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulfonamide.

Claim 12

The compound of claim 1, N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulfonamide.

Claim 13

The compound of claim 1, N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-(2-nitrophenyl)methanesulfonamide.

Claim 14

The compound of claim 1, 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.

Claim 15

The compound of claim 1, 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.

Claim 16

The compound of claim 1, 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.

Claim 17

The compound of claim 1, 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.

Claim 18

The compound of claim 1, 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.

Claim 19

The compound of claim 1, 2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.

Claim 20

The compound of claim 1, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-(2-methylsulfonyloxyphenyl)methanesulfonamide.

Claim 21

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.

Claim 22

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.

Claim 23

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.

Claim 24

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.

Claim 25

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.

Claim 26

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.

Claim 27

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.

Claim 28

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 13 and at least one of the following: surfactant, solid or liquid diluent.

Claim 29

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.

Claim 30

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.

Claim 31

A method of controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.

Claim 32

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.

Claim 33

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.

Claim 34

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.

Claim 35

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 7.

Claim 36

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 8.

Claim 39

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an herbicidally effective amount of a compound of claim 1 and an herbicidally effective amount of one or more compounds selected from the following: S-(4-chlorobenzyl)-N,N-diethylthiolcarbamate; 2-chloro-2',6'-diethyl-N-(butoxymethyl)acetanilide; S-ethyl-N,N-hexamethylene-thiolcarbamate; 1-α,α-dimethylbenzyl-3-p-tolylurea; 1-(α,α-dimethylbenzyl)-3-methyl-3-phenylurea; 2,4-dichlorophenyl-3-methoxy-4-nitrophenyl ether; 2,4,6-trichlorophenyl-4'-nitrophenyl ether; 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate; O-ethyl-O-(3-methyl-6-nitrophenol)-N-sec-butyl phosphoramid-thioate; S-(1-methyl-1-phenethyl)piperidine-1-carbathioate; 2-chloro-2',6'-diethyl-N-(N-propoxy-ethyl)acetanilide; 4-ethoxymethoxybenz-2',3'-dichloroanilide; 2-benzthiazol-2-iloxy-N-methylacetoanilide; 5-t-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazol-2-one; 3',4'-dichloropropionanilide; and N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine.

Claim 40

A method according to claim 37 where the compound of claim 1 is 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester.