Antidotes for sulfonylurea herbicides

Claim 2

A compound of the formula: where R is CO 2 CH 3 or CO 2 C 2 H 5 ; R 1 is H, Cl or CF 3 ; R 2 is C 1 -C 3 alkoxy or NR 3 R 4 ; R 3 is H, OCH 3 , C 1 -C 4 alkyl, cyclohexyl, C 1 -C 4 alkyl substituted with C 1 -C 4 alkyl substituted with C 1 -C 2 alkoxy or C 1 -C 4 alkyl substituted with ethoxyethoxy; R 4 is H or C 1 -C 2 alkyl; R 5 is H, Cl or OCH 3 ; provided that, in a compound of Formula I, when R is CO 2 CH 3 and R 2 is C 1 -C 3 alkoxy, then R 1 is other than H; and agriculturally suitable salts.

Claim 3

A compound of Claim 1 where R 1 is H.

Claim 4

A compound of Claim 1 where R 2 is NR 3 R 4 .

Claim 5

A compound of Claim 3 where R 1 is H.

Claim 6

A compound of Claim 4 where R 3 is H or C 1 -C 4 alkyl optionally substituted with unsubstituted phenyl or C 1 -C 2 alkoxy.

Claim 7

A compound of Claim 4 where R 4 is H.

Claim 8

A compound of Claim 3 where R 3 is other than C 4 -alkyl.

Claim 9

The compound of Claim 1 which is 2-[(aminocarbonyl)aminosulfonyl]benzoic acid, methyl ester and agriculturally suitable salts thereof.

Claim 10

The compound of Claim 1 which is 3-[(aminocarbonyl)aminosulfonyl]-2 -thiophenecarboxylic acid, methyl ester.

Claim 11

An agricultural composition comprising a non-phytotoxic antidotally effective amount of an antidotal compound of any of the preceding claims and at least one of (a) a surfactant and (b) a solid or liquid diluent.

Claim 12

Seed having a coating comprising a non-phytotoxic antidotally effective amount of a compound of any of claims 1 to 9.

Claim 13

The seed of claim 11 comprising from 0.1 to 0.5% of said compound, based on the seed weight.

Claim 14

1 3 . A method of protecting crop plants from injury due to an herbicial sulfonylurea compound of the formula where R 6 is CO 2 R 8 or Cl; R 7 is H, Cl or Cf3; R 8 is C 1 -C 3 alkyl; X is CH 3 or OCH3; Y is CH 3 , OCH 3 or Cl; and Z is CH or N; provided that (a) when Y is Cl, then Z is CH; and ( b ) when R 6 is Cl, then R 7 is H, X is CH 3 , Y is OCH 3 and Z is N; and their agriculturally suitable salts thereof, comprising combining application of an herbicidally effective amount of said herbicidal compound to the locus of said crop plants with application of a non-phytotoxic antidotally effective amount of an antidotal compound of the formulas where R is CO 2 CH 3 or CO 2 C 2 H 5 ; R 1 is H, Cl on CF 3 ; R 2 is C 1 -C 3 alkoxy or NR 3 R 4 ; R 3 is H, OCH 3 , C 1 -C 4 alkyl, cyclohexyl, C 1 -C 4 alkyl substituted with C 1 -C 4 alkyl substituted with C 1 -C 2 alkoxy or C 1 -C 4 alkyl substituted with ethoxyethoxy; R 4 is H or C 1 -C 2 alkyl; R 5 is H, Cl or OCH 3 ; and their agriculturally suitable salts, to the crop seed, to the crop plant or to the locus of the crop plant.

Claim 15

1 3 . A method of protecting crop plants from injury due to an herbicial sulfonylurea compound of the formula where R 6 is CO 2 R 8 or Cl; R 7 is H, Cl or Cf3; R 8 is C 1 -C 3 alkyl; X is CH 3 or OCH3; Y is CH 3 , OCH 3 or Cl; and Z is CH or N; provided that (a) when Y is Cl, then Z is CH; and ( b ) when R 6 is Cl, then R 7 is H, X is CH 3 , Y is OCH 3 and Z is N; and their agriculturally suitable salts thereof, comprising combining application of an herbicidally effective amount of said herbicidal compound to the locus of said crop plants with application of a non-phytotoxic antidotally effective amount of an antidotal compound of the formulas where R is CO 2 CH 3 or CO 2 C 2 H 5 ; R 1 is H, Cl on CF 3 ; R 2 is C 1 -C 3 alkoxy or NR 3 R 4 ; R 3 is H, OCH 3 , C 1 -C 4 alkyl, cyclohexyl, C 1 -C 4 alkyl substituted with C 1 -C 4 alkyl substituted with C 1 -C 2 alkoxy or C 1 -C 4 alkyl substituted with ethoxyethoxy; R 4 is H or C 1 -C 2 alkyl; R 5 is H, Cl or OCH 3 ; and their agriculturally suitable salts, to the crop seed, to the crop plant or to the locus of the crop plant.

Claim 16

A method of claim 13 wherein said antidotal compound is as defined in any of claims 2 to 9, except that the proviso in claim 1 does not apply.

Claim 17

A method of Claim 13 or 14 where the crop is selected from wheat, barley, corn, sorghum and soybean.

Claim 18

A method of Claim 13 or 14 where the crop is wheat.

Claim 19

A herbicidal composition comprising an herbicidally effective amount of an herbicidal sulfonylurea compound as defined in claim 13 and a non-phytotoxic antidotally effective amount of an antidotal compound of the formulas (I) or (II) as defined in claim 13.

Claim 20

The composition of claim 15 wherein said antidotal compound is as defined in any of claims 2 to 9, except that the proviso in claim 1 does not apply.

Claim 21

A method for the preparation of a compound of formula (I) or (II) as defined in claim 1 which comprises (a) reacting an isocyanate of formula wherein R and R 1 are as defined in claim 1, with an amine or alcohol of formula wherein R 2 is as defined in claim 1; or (b) reacting a sulfonamide of formula wherein R and R 1 are as defined in claim 1, with a C 1 -C 3 alkyl chloroformate, to prepare a compound of claim 1 wherein R 2 is C 1 -C 3 alkoxy; or (c) reacting a sulfonamide as defined in (b) above with wherein R 4 is C 1 -C 2 alkyl.