Benzofuran sulfamates

Claim 2

A compound of the formula: wherein Q is 0, S or SO 2 ; Q 1 is CR 3 R 4 or 0; L is OSO 2 NHCONHA; R 1 is H or C l -C 3 alkyl; R2 is H or C H 3 ; R 3 is H or CH 3 ; R 4 is H or CH 3 ; R 5 is H, CH 3 , OCH 3 , Cl, Br, N0 2 , CO 2 R 7 , SO 2 R 8 , OSO 2 R 9 or SO 2 NR 10 R 11 ; R 6 is H or C 1 -C 3 alkyl; R' 6 is H or C H 3 ; R 7 is C 1 -C 3 alkyl, CH 2 CH=CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 8 is C 1 -C 3 alkyl; R 9 is C 1 -C 3 alkyl or CF 3 ; R 10 and R 11 are independently C 1 -C 2 alkyl; A is X is CH 3 or OC H 3 ; Y is Cl, CH 3 , OCH3, OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 or ; and Z is CH or N; provided that (1) L is fixed at the 4- or 7-position; and when L is at the 4-position, then R 5 is at the 5-position, and when L is at the 7-position, then R 5 is at the 6-position; (2) in Formulae I and II, when Q is 0 and L is in the 4-position, and R 5 is other than H, then R 1 and R 6 are other than H; (3) in Formula II, when Q is 0 and L is in the 7-position, and R 5 is other than H, then R 6 and R 6 ' are other than H; (4) in Formula II, when Q is S or SO 2 and R 5 is other than H, Br or N0 2 , then R 6 and R 6 ' are other than H; (5) in Formula I, when Q is S, then R 5 is other than SO 2 R 8 ; (6) when Y is Cl, then Z is CH; (7) when Q 1 is 0, then Q is 0 and R 5 is H; and (8) the total number of carbon atoms in R 1 to R 4 are less than or equal to 4.

Claim 3

Compounds of Claim 1 where X is OCH 3 and Q 1 is 0 or CH 2 .

Claim 4

Compounds of Claim 2 where R 5 is H, Cl, CH 3 or CO 2 R 7 .

Claim 5

Compounds of Claim 3 which have the structure shown in Formula I and where L is in the 7-position.

Claim 6

Compounds of Claim 4 where R 5 is H.

Claim 7

Compounds of Claim 5 where Q is 0.

Claim 8

Compounds of Claim 5 where Q is S or S0 2 .

Claim 9

Compounds of Claim 6 where Y is CH 3 , OCH 3 , OC 2 H 5 or CH 2 OCH 3 and R 1 and R 2 are independently H or CH 3 .

Claim 10

Compounds of Claim 7 where Y is CH 3 , OC H 3 , OC 2 H 5 or CH 2 OCH 3 and R 1 and R 2 are independently H or CH 3 .-

Claim 11

The compound of.Claim 1, N-[(4,6-dimethoxy- pyrimidin-2-yl)aminocarbonyl]sulfamic acid, 2,3-dihy- dro-2,2-dimethylbenzofuran-7-yl ester.

Claim 12

The compound of Claim 1, N-[(4-methyl-6-methoxypyrimidin-2-yl)aminocarbonyl]sulfamic acid, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl ester.

Claim 13

The compound of Claim 1, N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]sulfamic acid, 2,3-di- hydro-2,2-dimethylbenzofuran-7-yl ester.

Claim 14

The compound of Claim 1, N-[(4-methyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]sulfamic acid, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl ester.

Claim 15

Compounds of claim 1 wherein: Q 1 is CR 3 R 4 ; R 1 is H or CH 3 ; R 6 is H or CH 3 Y is Cl, CH 3 , OCH 3 , OC 2 H 5 or CH 2 OCH 3 ; and Q, L, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , A, X and Z are as defined in claim 1.

Claim 16

15 . A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a herbicidal compound and at least one of the following: surfactant, solid or liquid diluent, characterised in that said herbicidal compound comprises a compound of any of Claims 1 to 14.

Claim 17

1 6. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a herbicidal compound, characterised in that said herbicidal compound comprises a compound of any of Claims 1 to 14.

Claim 19

A process for preparing a compound of Claim 1 comprising contacting an aryloxysulfonylisocyanate of the formula: with an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of the formula: where Q, Q 1 , R 1 , R 2 , R 5 , R 6 , R 6 ', X, Y and Z are as defined in Claim 1.

Claim 20

A process for the preparation of a compound of the formula: wherein Q is 0, S or SO 2 ; Q 1 is CR 3 R 4 or 0; L is OSO 2 NHCONHA; R 1 is H or C 1 -C 3 alkyl; R 2 is H or CH 3 ; R 3 is H or CH3; R 4 is H or CH 3 ; R 5 is H, CH 3 , OCH 3 , Cl, Br, N0 2 , CO 2 R 7 , SO 2 R 8 , OSO 2 R 9 or SO 2 NR 10 R 11 ; R 6 is H or C 1 -C 3 alkyl; R 6 ' is H or CH 3 ; R 7 is C 1 -C 3 alkyl, CH 2 CH=CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 8 is C 1 -C 3 alkyl; R9 is C 1 -C 3 alkyl or CF 3 ; R 10 and R 11 are independently C 1 -C 2 alkyl; A is X is CH 3 or OCH 3 ; Y is Cl, CH 3 , OC H 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 or ; and Z is CH or N; provided that (1) L is fixed at the 4- or 7-position; and when L is at the 4-position, then R 5 is at the 5-position; and when L is at the 7-position, then R 5 is at the 6-position; . (2) in Formulae I and II, when Q is 0 and L is in the 4-position, and R 5 is other than H, then R 1 and R 6 are other than H; (3) in Formula II, when Q is 0 and L is in the 7-position, and R 5 is other than H, then R 6 and R 6 ' are other than H; ( 4 ) in Formula II, when Q is 5 or 50 2 and R 5 is other than H, Br or NO 2 , then R 6 and R 6 ' are other than H; (5) in Formula I, when Q is S, then R 5 is other than SO 2 R 8 ; (6) when Y is Cl, then Z is CH; (7) when Q 1 is 0, then Q is 0 and R 5 is H; and (8) the total number of carbon atoms in R 1 to R 4 are less than or equal to 4. which comprises contracting an aryloxysulfonylisocyanate. of the formula: with an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of the formula: where Q, Q 1 , R 1 , R 2 , R 5 , R 6 , R 6 ', X, Y and Z are as defined above.

Claim 21

A process for the preparation of a compound of the formula: wherein Q is 0, S or SO 2 ; Q 1 is CR 3 R 4 or 0; L is OSO 2 NHCONHA; R 1 is H or C 1 -C 3 alkyl; R 2 is H or CH 3 ; R 3 is H or CH3; R 4 is H or CH 3 ; R 5 is H, CH 3 , OCH 3 , Cl, Br, N0 2 , CO 2 R 7 , SO 2 R 8 , OSO 2 R 9 or SO 2 NR 10 R 11 ; R 6 is H or C 1 -C 3 alkyl; R 6 ' is H or CH 3 ; R 7 is C 1 -C 3 alkyl, CH 2 CH=CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 8 is C 1 -C 3 alkyl; R9 is C 1 -C 3 alkyl or CF 3 ; R 10 and R 11 are independently C 1 -C 2 alkyl; A is X is CH 3 or OCH 3 ; Y is Cl, CH 3 , OC H 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 or ; and Z is CH or N; provided that (1) L is fixed at the 4- or 7-position; and when L is at the 4-position, then R 5 is at the 5-position; and when L is at the 7-position, then R 5 is at the 6-position; . (2) in Formulae I and II, when Q is 0 and L is in the 4-position, and R 5 is other than H, then R 1 and R 6 are other than H; (3) in Formula II, when Q is 0 and L is in the 7-position, and R 5 is other than H, then R 6 and R 6 ' are other than H; ( 4 ) in Formula II, when Q is 5 or 50 2 and R 5 is other than H, Br or NO 2 , then R 6 and R 6 ' are other than H; (5) in Formula I, when Q is S, then R 5 is other than SO 2 R 8 ; (6) when Y is Cl, then Z is CH; (7) when Q 1 is 0, then Q is 0 and R 5 is H; and (8) the total number of carbon atoms in R 1 to R 4 are less than or equal to 4. which comprises contracting an aryloxysulfonylisocyanate. of the formula: with an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of the formula: where Q, Q 1 , R 1 , R 2 , R 5 , R 6 , R 6 ', X, Y and Z are as defined above.

Claim 22

The process of claim 1 wherein: Q 1 is CR 3 R 4 ; R i is H or CH 3 ; R 6 is H or CH 3 ; Y is Cl, CH 3 , OCH 3 , OC 2 H 5 or CH 2 OCH 3 ; and Q, L , R2, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , A, X and Z are as defined in claim 1.

Claim 23

The process of claim 1 or 2 where X is OCH 3 and Q 1 is O or C H 2 .

Claim 24

The process of claim 3 where R 5 is H, Cl, CH 3 or CO 2 R 7 .

Claim 25

The process of claim 4 which have the structure shown in Formula I and where L is in the 7-position.

Claim 26

The process of Claim 5 where R 5 is H.

Claim 27

The process of Claim 6 where Q is 0.

Claim 28

The process of Claim 6 where Q is S or SO 2 .

Claim 29

The process of Claim 7 where Y is CH 3 , OCH 3 , OC 2 H 5 or CH 2 OCH 3 and R 1 and R 2 are independently H or CH 3 .

Claim 30

1 0. The process of Claim 8 where Y is CH 3 , OCH 3 , OC 2 H 5 or CH 2 OCH 3 and R 1 and R 2 are independently H or CH 3 .

Claim 31

The process of Claim 1 wherein the product is a compound selected from N-[(4,6-dimethoxy- pyrimidin-2-yl)aminocarbonyl]sulfamic acid. 2,3-dihy- dro-2,2-dimethylbenzofuran-7-yl ester; N-[(4-methyl-6-methoxypyrimidin-2-yl)aminocarbonyl]sulfamic acid, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl ester; N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl)sulfamic acid, 2,3-di- hydro-2,2-dimethylbenzofuran-7-yl ester; and N-[(4-methyl-6-methoxy-l,3,5-triazin-2-yl)aminocarbonyl]sulfamic acid, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl ester.