Herbicidal sulfonamides

Claim 2

A compound of the formula: wherein J is or and Q is 0, S or SO 2 ; R is H or CH 3 ; R 1 is H , CH 3 , OCH 3 , Cl , Br, CO 2 R 5 , SO 2 R 6 , OSO 2 R 7 or SO 2 NR 8 R 9 ; R 2 and R 3 are independently H or C 1 -C 3 alkyl; R 4 is H or CH 3 ; R 5 is C 1 -C 3 alkyl, CH 2 CH=CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 6 is C l -C 3 alkyl; R 7 is C l -C 3 alkyl or CF 3 ; R 8 and R 9 are independently C l -C 2 alkyl; A is G is 0 or CH 2 ; X is CH 3 , OCH 3 or Cl; X 1 is CH 3 , OCH 3 or OC 2 H 5 ; Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , C 2 H 5 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; Z is CH or N; and their agriculturally suitable salts provided that 1) when X is Cl, then Z is CH and Y is OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 or OC 2 H 5 ; 2) the total number of carbon atoms in R 2 and R 3 are less than or equal to 3; 3) In Structure J 2 when R 2 and R 3 is other than H, then R 4 is H; 4) In Structure J 3 when R 2 is other than H, then R 4 is H; 5 ) when Q is S, then R 1 is not SO 2 NR 8 R 9 ; 6) In Structures J 3 and J 6 , Q may not be 0; and 7) In Formula J 7 , R 1 is not CH 3 .

Claim 3

Compounds of Claim 1 where J is J 1 .

Claim 4

Compounds of Claim 1 where J is J 2 .

Claim 5

Compounds of Claim 1 where J is J 3 .

Claim 6

Compounds of Claim 1 where J is J 4 .

Claim 7

Compounds of Claim 1 where J is J 5 .

Claim 8

Compounds of Claim 1 where J is J 6 .

Claim 9

Compounds of Claim 1 where J is J 7 .

Claim 10

Compounds of any of Claims 2 to 8 where R is H.

Claim 11

Compounds of Claim 9 where R 1 is H.

Claim 12

Compounds of claim 10 where A is and X is OCH 3 or Cl.

Claim 13

OCH 3 . 12. Compounds of Claim 11 where Y is CH 3 or

Claim 14

The compound of Claim 1 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3,4-dihydro-2H-1-benzothiopyran-8-sulfonamide, 1,1-dioxide.

Claim 15

1 4. The compound of Claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3,4-dihydro-2H-1-benzothiopyran-8-sulfonamide, 1,1-dioxide.

Claim 16

The compound of Claim 1 which is N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-3,4-dihydro-2H-1-benzothiopyran-8-sulfonamide, 1,1-dioxide.

Claim 17

A compound of the formula: wherein J' is and Q is 0, S or SO 2 ; Q 1 is 0, S, SO or SO 2 ; R is H or C H 3 ; R' 1 is H , CH 3 , OCH 3 , Cl , B r, N0 2 , CO 2 R 5 , SO 2 R 6 , OSO 2 R 7 or SO 2 NR 8 R 9 ; R 2 is H or C 1 -C 3 alkyl; R 3 is H or CH 3 ; R4 is H or C H 3 ; R4 is H, Cl, CH 3 , CF 3 , OCH 3 or Br; R 5 is C 1 -C 3 alkyl, CH 2 CH=CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 6 is C 1 -C 3 alkyl; R 7 is C l -C 3 alkyl or CF 3 ; R 8 and R 9 are independently C 1 -C 2 alkyl; R 10 is H, C1, Br or C 1 -C 3 alkyl; R 11 is H, CH 3 , Cl or Br; W is 0 or S; A' is G is 0 or C H 2 ; X' is H, CH 3 , OCH 3 or Cl; X 1 is CH 3 , OCH 3 or OC 2 H 5 ; X 2 is CH 3 , C 2 H 5 or C H 2 C F 3 ; Y' is CH 3 , OCH 3 , OC 2 H 5 , CH 2 0CH 3 , NH 2 , NHCH 3' N(C H 3 ) 2 ; CH(OCH 3 ) 2 , , C 2 H 5 , CF 3 , C H 2 =CHCH 2 0, SCH 3 , HC≡CCH 2 O or CF 3 CH 2 0; Y 2 is C 2 H 5 , CH 3 , OCH 3 , OC 2 H 5 , SCH 3 or SC 2 H 5 ; and Z' is CH, N, CCH 3 , CC 2 H 5 , CC1 or CBr; and their agriculturally suitable salts provided that 1) In Structures J i and J' 2 , when Q 1 is 0 and R i is other than H, Cl, Br or N0 2 , then at least one of R 2 and R 3 is alkyl, and when Q is S, then R i cannot be NO 2 ; 2) In Structure J' 3 , when Ri is N0 2 or SO 2 NR 8 R 9 , then R 10 is C l - C 3 alkyl and R 11 is CH 3 ; 3) when X' is Cl, then Z' is CH and Y' is OCH 3 , NH 2 , NHCN 3 or N(CH 3 ) 2 ; 4 ) when Q 1 is S0, then W is 0; and 5) when R' 4 is other than H, then R i is H.

Claim 18

A compound of the formula: wherein J' is and Q is 0, S or SO 2 ; Q 1 is 0, S, SO or SO 2 ; R is H or C H 3 ; R' 1 is H , CH 3 , OCH 3 , Cl , B r, N0 2 , CO 2 R 5 , SO 2 R 6 , OSO 2 R 7 or SO 2 NR 8 R 9 ; R 2 is H or C 1 -C 3 alkyl; R 3 is H or CH 3 ; R4 is H or C H 3 ; R4 is H, Cl, CH 3 , CF 3 , OCH 3 or Br; R 5 is C 1 -C 3 alkyl, CH 2 CH=CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 6 is C 1 -C 3 alkyl; R 7 is C l -C 3 alkyl or CF 3 ; R 8 and R 9 are independently C 1 -C 2 alkyl; R 10 is H, C1, Br or C 1 -C 3 alkyl; R 11 is H, CH 3 , Cl or Br; W is 0 or S; A' is G is 0 or C H 2 ; X' is H, CH 3 , OCH 3 or Cl; X 1 is CH 3 , OCH 3 or OC 2 H 5 ; X 2 is CH 3 , C 2 H 5 or C H 2 C F 3 ; Y' is CH 3 , OCH 3 , OC 2 H 5 , CH 2 0CH 3 , NH 2 , NHCH 3' N(C H 3 ) 2 ; CH(OCH 3 ) 2 , , C 2 H 5 , CF 3 , C H 2 =CHCH 2 0, SCH 3 , HC≡CCH 2 O or CF 3 CH 2 0; Y 2 is C 2 H 5 , CH 3 , OCH 3 , OC 2 H 5 , SCH 3 or SC 2 H 5 ; and Z' is CH, N, CCH 3 , CC 2 H 5 , CC1 or CBr; and their agriculturally suitable salts provided that 1) In Structures J i and J' 2 , when Q 1 is 0 and R i is other than H, Cl, Br or N0 2 , then at least one of R 2 and R 3 is alkyl, and when Q is S, then R i cannot be NO 2 ; 2) In Structure J' 3 , when Ri is N0 2 or SO 2 NR 8 R 9 , then R 10 is C l - C 3 alkyl and R 11 is CH 3 ; 3) when X' is Cl, then Z' is CH and Y' is OCH 3 , NH 2 , NHCN 3 or N(CH 3 ) 2 ; 4 ) when Q 1 is S0, then W is 0; and 5) when R' 4 is other than H, then R i is H.

Claim 19

Compounds of Claim 16 where J' is Ji and R 4 is H.

Claim 20

Compounds of Claim 16 where J' is J' 2 .

Claim 21

Compounds of Claim 17 or 18 where W is O and R is H.

Claim 22

Compounds of Claim 19 where Ri is H, Cl, CH 3 , OCH 3 , CO 2 R 5 or SO 2 R 6 .

Claim 23

Compounds of Claim 43 where R' 4 (if present) and Ri are H and R 2 and R 3 are independently H or CH 3 .

Claim 24

Compounds of Claim 16 where J' is J' 3 , W is O and R is H.

Claim 25

Compounds of Claim 22 where R 11 is H and R' 1 is H, Cl, CH 3 , OCH 3 , CO 2 R 5 or SO 2 R 6 and SO 2 NHC(W)NRA' is bonded to the 7-position.

Claim 26

Compounds of Claim 23 where R' 1 is H and R 10 is H or CH 3 .

Claim 27

Compounds of Claims 21 or 24 where A' is ; Z' is CH or N; and X' is CH 3 , OCH 3 or Cl.

Claim 28

Compounds of Claim 57 where Y' is CH 3 , OCH 3 , CH 2 OCH 3 or N(CH 3 ) 2 .

Claim 29

The compound of Claim 16 which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.

Claim 30

The compound of Claim 16 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.

Claim 31

The compound of Claim 16 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.

Claim 32

The compound of Claim 16 which is N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.

Claim 33

The compound of Claim 16 which is N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.

Claim 34

The compound of Claim 16 which is N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-di- hydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.

Claim 35

The compound of Claim 16 which is 2,3-dihy- dro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylbenzofuran-7-sulfonamide.

Claim 36

The compound of Claim 16 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methylbenzofuran-7-sulfonamide.

Claim 37

The compound of Claim 1 6 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydroben- zo[b]thiophene-7-sulfonamide, 1,1-dioxide.

Claim 38

The compound of Claim 16 which is 2,3-dihy- dro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzo[b]thiophene-7-sulfonamide, 1,1-dioxide.

Claim 39

A compound of Claim 16 wherein J' is J' 1 or J' 3 ; R' 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are as defined in Claim 16; R' 4 is H , R 10 is H, CH 3 , Cl or Br, W is 0, Q is O,S or SO 2 , A' is as defined in Claim 16 excepting X', X 1 , G and Z' are as defined in Claim 16, Y' is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 or N(CH 3 ) 2 .

Claim 40

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of any of Claims 1 to 37 and at least one of the following: surfactant, solid or liquid diluent.

Claim 44

A compound of the formula: where Q 1 is 0, S or SO 2 ; R 2 is H or C 1 -C 3 alkyl; R 3 is H or CH 3 ; and R 4 is H or CH 3 .

Claim 45

A compound of the formula: where Q 1 is 0, S or SO 2 ; R 2 is H or C 1 -C 3 alkyl; R 3 is H or CH 3 ; and R 4 is H or CH 3 .