EP0074282A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Herbicidal alkyl sulfones
Assignee: EIDP Inc
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Filing: 1982-09-09
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Granted: —
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Expires: 2002-09-09
Abstract
Abstract Compounds of the formula wherein R is S(O) n CH(R 2 )A, A is selected from various organic groups or cyano, R, is H, halogen, CH 3 , OCH 3 , CF 3 or NO 2 , n is 0, 1 or 2, X is CH 3 , OCH 3 or Cl, Y is CH 3 , C 2 H s , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 or N(CH 3 ) 2 , and Z is CH or N, and their agriculturally suitable salts, exhibit herbicidal and plant growth regulant effects. The novel compounds may be formulated into agricultural compositions by conventional methods. The compounds may be prepared by various routes, e.g. by reacting an appropriately substitued benzenesulfonyl isocyanate with the appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine.
Inventors
- 👤 Gerald Edward Lepone
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 14:34
CPC Classifications
C; C07; C07C; C07C311/00; C07C311/65; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D; C07D521/00
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
342 words
A compound of the formula: wherein R is S(O) n CH(R 2 )A; A is OR 3 , CH 2 OR 3 , OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , S(O) p R 3 , CH 2 S(O) p R 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN, CH 2 OH, CH(OH)CH 3 , CH 2 CH 2 OH, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCH 3 ) 2 or R 1 and R 4 are independently H, F, Cl, Br, CH 3 , OCH 3 , CF 3 or N 0 2 ; R 2 is H or CH 3 ; R 3 is C 1 -C 2 alkyl; n is 0, 1 or 2; p is 0, 1 or 2; X is CH 3 , OCH 3 or Cl; Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; and Z is CH or N; and their agriculturally suitable-salts; provided that: (1) when X is Cl then Z is CH; (2) when X is Cl and Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH3 or OC 2 H 5 then A is OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN, CN, CH 2 CN, , CH 2 OH, CH(OH)CH 3 , CH 2 CH 2 0H, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, DH(OCH 3 ) 2 or (3) when X is Cl and A is DR 3 , CH 2 OR 3 , S(O) p R 3 or CH 2 S(O) p R 3 , then Y is HH 2 , NHCH 3 or N(CH 3 ) 2 .
Claim 2
Dependent Claim
342 words
A compound of the formula: wherein R is S(O) n CH(R 2 )A; A is OR 3 , CH 2 OR 3 , OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , S(O) p R 3 , CH 2 S(O) p R 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN, CH 2 OH, CH(OH)CH 3 , CH 2 CH 2 OH, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCH 3 ) 2 or R 1 and R 4 are independently H, F, Cl, Br, CH 3 , OCH 3 , CF 3 or N 0 2 ; R 2 is H or CH 3 ; R 3 is C 1 -C 2 alkyl; n is 0, 1 or 2; p is 0, 1 or 2; X is CH 3 , OCH 3 or Cl; Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; and Z is CH or N; and their agriculturally suitable-salts; provided that: (1) when X is Cl then Z is CH; (2) when X is Cl and Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH3 or OC 2 H 5 then A is OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN, CN, CH 2 CN, , CH 2 OH, CH(OH)CH 3 , CH 2 CH 2 0H, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, DH(OCH 3 ) 2 or (3) when X is Cl and A is DR 3 , CH 2 OR 3 , S(O) p R 3 or CH 2 S(O) p R 3 , then Y is HH 2 , NHCH 3 or N(CH 3 ) 2 .
Claim 3
Dependent Claim
67 words
Compounds of Claim 1 where A is OCH 2 CH 2 OCH 3 ; CH 2 OCH 2 CH 2 OCH 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CH 2 CN, CH(OH)CH 3 , , CH 2 OH, CH 2 CH 2 ON, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCH 3 ) 2 or
Claim 4
Dependent Claim
22 words
Compounds of Claim 2 where A is CO 2 R 3 or CN; R 1 is H; and X is not C1.
Claim 5
Dependent Claim
18 words
Compounds of Claim 1 where Y is NH 2 , NHCH 3 or N(CH 3 ) 2 .
Claim 6
Dependent Claim
9 words
The compound of Claim 1 which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(2-methoxy- ethylsulfonyl)benzenasulfonamide.
Claim 7
Dependent Claim
8 words
The compound of Claim 1 which is 2-(2-methoxyethylsulfonyl)-N-[(4-methoxy-5-methylpyrimidin-2-yl)aaminocarbonyl]benzenesulfonamide.
Claim 8
Dependent Claim
10 words
The compound of Claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl ]-Z-(2-methoxy- ethylsulfonyl)benzenesulfonamide.
Claim 9
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfonyl)benzenesulfonamide.
Claim 10
Dependent Claim
8 words
The compound of Claim 1 which is 2-(2-methoxyethylsulfonyl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide.
Claim 11
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfonyl)benzenesulfonamide.
Claim 12
Dependent Claim
9 words
The compound of Claim 1 which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(cyanomethyl- thio)benzenesulfonamide.
Claim 13
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benzenesulfonamide.
Claim 14
Dependent Claim
9 words
The compound of Claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(cyanomethyl- thio)benzenesulfonamide.
Claim 15
Dependent Claim
9 words
The compound of Claim 1 which is N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyano- methylthio)benzenesulfonamide.
Claim 16
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benzenesulfonamide.
Claim 17
Dependent Claim
9 words
The compound of Claim 1 which is N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyano- methylthio)benzenesulfonamide.
Claim 18
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl.1-2-(2-(methoxy-2-oxoethylsulfonyl)benzenesulfonamide.
Claim 19
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-methoxy-2-oxoethylsulfonyl)benzenesulfonamide.
Claim 20
Dependent Claim
8 words
The compound of Claim 1 which is N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxy-2-oxoethylsulfonyl)benzenesulfonamide.
Claim 21
Dependent Claim
116 words
A compound of claim 1 wherein A is OR 3 , CH 2 OR 3 , OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , S(O) p R 3 , CH 2 S(O) p R 3 . CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN or X is CH 3 or OCH 3 ; Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 or OC 2 H 5 ; and R, R 1 , R 2 , R 3 , R 4 , n, p and Z are as defined in claim 1.
Claim 22
Dependent Claim
46 words
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 20.
Claim 23
Independent Claim
40 words
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 20.
Claim 24
Independent Claim
44 words
A method for regulating the growth of plants by applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterised in that said plant growth regulant comprises a compound of any of claims 1 to 20.
Claim 25
Dependent Claim
119 words
A process for making a compound of claim 1 which comprises (A), reacting a sulfonyl isocyanate of formula wherein R is SCH(R 2 )A or SO 2 CH(R 2 )A and A and R 2 are as defined in claim 1, with an amine of formula wherein X, Y and Z are as defined in claim 1; or (B) reacting a sulfonamide of formula wherein R and R are as defined in claim 1, with a heterocyclic carbamate of formula wherein X, Y and Z are as defined in claim 1; or (C) reacting the sulfonamide of formula (IV) defined above with an appropriate sulfonyl carbamate of formula wherein R and R 1 are as defined in claim 1.
Claim 26
Dependent Claim
528 words
A process for the preparation of a compound of the formula: wherein R is S(O) n CH(R 2 )A; A is OR 3 , CH 2 OR 3 , OCH 2 CH 2 OCH 3 , CH 2 OCN 2 CH 2 OCH 3 , S(O) p R 3 , CH 2 S(O) p R 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN, CH 2 OH, CH(OH)CH 3 , CH 2 CH 2 OH, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCH 3 ) 2 or R 1 and R 4 are independently H, F, Cl, B r, CH 3 , OCH 3 , CF 3 or N0 2 ; R 2 is H or C H 3 ; R 3 is C 1 -C 2 alkyl; n is 0, 1 or 2; p is 0, 1 or 2; X is -CH 3 , OCH 3 or Cl; Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; and Z is CH or N; and agriculturally suitable salts; provided that: (1). when X is Cl then Z is CH; (2) when X is Cl and Y is CH 3 , C 2 H 5 . CH 2 OCH 3 , OCH 3 or OC 2 H 5 then A is OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CH, CH 2 CN, , CH 2 0H, CH(OH)CH 3 , CH 2 CH 2 OH, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCN 3 ) 2 or (3) when X is Cl and A is OR 3 , CH 2 OR 3 , S(0)pR 3 or CH 2 S(O) p R 3 , then Y is NH 2 , NHCH 3 or N(CH 3 ) 2 ; which comprises. (A) reacting a sulfonyl isocyanate of formula wherein R is SCH(R 2 )A or SO 2 CH(R 2 )A and A and R 2 are as defined above, with an amine of formula wherein X, Y and Z are as defined above; or (B) reacting a sulfonamide of formula wherein R and R 1 are as defined above, with a heterocyclic carbamate of formula wherein X, Y and Z are as defined above; or (C) reacting the sulfonamide of formula (IV) defined above with an appropriate sulfonyl carbamate of formula wherein R and R 1 are as defined above; or ( D ) oxidising a compound of formula (I) wherein R is SCH (R 2 ) A to a corresponding compound wherein R is SO.CH(R 2 )A by methods known per se; or . (E) deprotecting a derivative wherein A is a protected hydroxyalkyl group to obtain a compound of formula (I) wherein A is a hydroxyalkyl group; or (F) reacting the sulfonamide of formula (IV) defined above with an isocyanate of formula wherein X, Y and Z are as defined above.
Claim 27
Dependent Claim
528 words
A process for the preparation of a compound of the formula: wherein R is S(O) n CH(R 2 )A; A is OR 3 , CH 2 OR 3 , OCH 2 CH 2 OCH 3 , CH 2 OCN 2 CH 2 OCH 3 , S(O) p R 3 , CH 2 S(O) p R 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN, CH 2 OH, CH(OH)CH 3 , CH 2 CH 2 OH, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCH 3 ) 2 or R 1 and R 4 are independently H, F, Cl, B r, CH 3 , OCH 3 , CF 3 or N0 2 ; R 2 is H or C H 3 ; R 3 is C 1 -C 2 alkyl; n is 0, 1 or 2; p is 0, 1 or 2; X is -CH 3 , OCH 3 or Cl; Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; and Z is CH or N; and agriculturally suitable salts; provided that: (1). when X is Cl then Z is CH; (2) when X is Cl and Y is CH 3 , C 2 H 5 . CH 2 OCH 3 , OCH 3 or OC 2 H 5 then A is OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CH, CH 2 CN, , CH 2 0H, CH(OH)CH 3 , CH 2 CH 2 OH, C(O)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCN 3 ) 2 or (3) when X is Cl and A is OR 3 , CH 2 OR 3 , S(0)pR 3 or CH 2 S(O) p R 3 , then Y is NH 2 , NHCH 3 or N(CH 3 ) 2 ; which comprises. (A) reacting a sulfonyl isocyanate of formula wherein R is SCH(R 2 )A or SO 2 CH(R 2 )A and A and R 2 are as defined above, with an amine of formula wherein X, Y and Z are as defined above; or (B) reacting a sulfonamide of formula wherein R and R 1 are as defined above, with a heterocyclic carbamate of formula wherein X, Y and Z are as defined above; or (C) reacting the sulfonamide of formula (IV) defined above with an appropriate sulfonyl carbamate of formula wherein R and R 1 are as defined above; or ( D ) oxidising a compound of formula (I) wherein R is SCH (R 2 ) A to a corresponding compound wherein R is SO.CH(R 2 )A by methods known per se; or . (E) deprotecting a derivative wherein A is a protected hydroxyalkyl group to obtain a compound of formula (I) wherein A is a hydroxyalkyl group; or (F) reacting the sulfonamide of formula (IV) defined above with an isocyanate of formula wherein X, Y and Z are as defined above.
Claim 28
Dependent Claim
186 words
A process of claim 1 wherein A is OR 3 , CH 2 OR 3 , OCH 2 CH 2 OCH 3 . CH 2 OCH 2 CH 2 OCH 3 , S(O) p R 3 , CH 2 S(O) p R 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CN or X is CH 3 or OCH 3 ; Y is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 or OC 2 H 5 ; and R, R 1 , R 2 , R 3 , R 4 , n, p and Z are as defined in claim 1. 3. A process of Claim 1 or 2 where A is OCN 2 CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CO 2 R 3 , CH 2 CO 2 R 3 , CN, CH 2 CH 2 CN, CH(OH)CH 3 , CH 2 OH, CH 2 CH 2 OH, C(C)CH 3 , CH 2 C(O)CH 3 , CHO, CH(OCH 3 ) 2 or
Claim 29
Dependent Claim
23 words
A process of Claim 3 where A is CO 2 R 3 or CN; R 1 is H; and X is not C1.
Claim 30
Dependent Claim
20 words
A process of Claim 1 or 2 where Y is NH 2 , NHCH 3 or N(CH 3 ) 2'
Claim 31
Dependent Claim
42 words
A process of Claim 1 wherein the product is a compound of formula (I) selected from N-[(4,6-dimethylpyrimidin-2-yl)aninocarbonyl]-2-(2-methoxy- ethylsulfonyl)benzenesulfonamide; 2-(2-methoxyethylsulfonyl)-N-[(mathoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2(-2methoxy- ethylsulfonyl)benzenesulfonamide; N-[(4,6-dimethyl-1,3,5-triazin-2-yl)-aminocarbonyl]-2-(2-methoxyethylsulfonyl)benzenesulfonamide; 2-(2-methoxyethylsulfonyl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide; N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfonyl)benzenesulfonamide; N -[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(cyanomethyl- thio)benzenesulfonamide; N-[(4-methoxy-6-methylpyrinidir-2-yl) arninocarbonyl]-2-(cyanomethylthio)benzenesuifonamide; N- [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(cyanomethyl- thio)benzenesulfonamide N-[(4,5-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyano- rrethyithio)benzen-esulfonamide: N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyanomethylthio)6enzenesulfonamide: N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyano- methylthio)benzenesulfonamide; N-( 4,5-dimethylpyrimidin-2-yl)an)inocarbonyl]-2-(2-(methoxy-2-oxoethylsulfonyl)benzenesulfonamide; N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2(2-methoxy-2-oxsethylsulfonyl)benzenesulfonamide; or N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-nethoxy-2-oxethylsulfonyl)benzsnesulfonamide.
Claim 32
Independent Claim
46 words
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 formula (I) as defined in any of claims 1 to 5.
Claim 33
Dependent Claim
18 words
The method of Claim 7 wherein said compound of formula I is a compound defined in claim 6.
Claim 34
Independent Claim
49 words
A method for regulating the growth of plants by applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant, characterised in that said plant growth regulant comprises a compound of formula (I) as defined in any of claims 1 to 6.
References Cited (Backward Citations)
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