EP0023140A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Herbicidal sulfonamides, preparation and use thereof, and compositions containing them
Assignee: EIDP Inc
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Filing: 1980-07-18
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Granted: —
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Expires: 2000-07-18
Abstract
Abstract Compounds of the general formula wherein A is B is Cl or Br: R is carboxylic ester, amide, Cl, CF 3 , N0 2 or various sulfur containing groups: R 1 is H, halogen, NO 2 , CH 3 , OCH, or CF,; X and Z are independently H, CH 3 , Bf, Cl, OCH 3 , CH 2 CH 3 , CH 2 OCH 3 or OCH 2 CH 3 ; and Y is halogen, CN, NO or various organic groups; and their agriculturally suitable salts; exhibit potent herbicidal activity. Some can also be used to regulate plant growth. The compounds can be made by reacting the appropriately substituted benzenesulfonyl or pyridinesulfonyl isocyanate with the appropriate 2-aminopyrimidine they can be formulated for agricultural use in conventional manner. Compounds wherein R is carboxyl are of interest as intermediates for the preparation of the compounds (I).
Inventors
- 👤 George Levitt
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 18:10
CPC Classifications
C; C07; C07C; C07C311/00; C07C311/65; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; C07D213/71; C07D521/00
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
420 words
A compound of the general formula: wherein A is B is Cl or Br; O O R is CO 2 R 2 , - -NR 2 a R 2 b , - -SR 2 c , SO 2 NR 3 R 4 , Cl, CF 3 , NO 2 or S(O) n R 3 where n is 0, 1 or 2; R 1 is H, Cl, F, Br, NO 2 , CH 3 , OCH 3 or CF 3 ; R 2 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, C 2 -C 3 haloalkyl, C 5 -C 6 cycloalkyl, C 4 -C 7 c y c l o-alkylalkyl, CH 2 OCH 2 CH 2 OCH 3 , CH 2 -CH(CH 3 )OR 5 or (CH 2 ) m OR 5 where m is 1, 2 or 3 ; R is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or OCH 3 ; R b is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or and can be taken together to form (̵CH 2 )̵ 5 , (̵CH 2 )̵ 4 or -CH 2 CH 2 -O-CH 2 CH 2 -; is C 1 -C 4 alkyl or C 3 -C 4 alkenyl; R 3 is C 1 -C 4 alkyl or OCH 3 ; R 4 is C 1 -C 4 alkyl; . R is C 1 -C 3 alkyl; X and Z are independently H, CH 3 , Br, Cl, OCH 3 , CH 2 CH 3 , CH 2 OCH 3 or OCH 2 CH 3 ; and Y is F, Cl, Br, I, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , (CH 2 ) 3 CH 3 , CH 2 -CH=CH 2 , OCH 3 , OCH 2 CH 3 , CN, CH2CH2Cl, CH 2 CH 2 CH 2 Cl, CH 2 CH 2 OCH 3 , OCH 2 OCH 3 , CH 2 OCH 3 , OCH 2 CH 2 OCH 3 , CH 2 CO 2 R 6 , CH 2 CH 2 CO 2 R 6 , CO 2 R 6 , or NO; R is CH 3 or CH 2 CH 3 ; and their agriculturally suitable salts; provided that: 1) when is OCH 3 , then is CH 3 ; 2) when R 3 is OCH 3 , then R 4 is CH 3 ; and 3) when R is Cl, then Y is F.
Claim 2
Dependent Claim
420 words
A compound of the general formula: wherein A is B is Cl or Br; O O R is CO 2 R 2 , - -NR 2 a R 2 b , - -SR 2 c , SO 2 NR 3 R 4 , Cl, CF 3 , NO 2 or S(O) n R 3 where n is 0, 1 or 2; R 1 is H, Cl, F, Br, NO 2 , CH 3 , OCH 3 or CF 3 ; R 2 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, C 2 -C 3 haloalkyl, C 5 -C 6 cycloalkyl, C 4 -C 7 c y c l o-alkylalkyl, CH 2 OCH 2 CH 2 OCH 3 , CH 2 -CH(CH 3 )OR 5 or (CH 2 ) m OR 5 where m is 1, 2 or 3 ; R is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or OCH 3 ; R b is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or and can be taken together to form (̵CH 2 )̵ 5 , (̵CH 2 )̵ 4 or -CH 2 CH 2 -O-CH 2 CH 2 -; is C 1 -C 4 alkyl or C 3 -C 4 alkenyl; R 3 is C 1 -C 4 alkyl or OCH 3 ; R 4 is C 1 -C 4 alkyl; . R is C 1 -C 3 alkyl; X and Z are independently H, CH 3 , Br, Cl, OCH 3 , CH 2 CH 3 , CH 2 OCH 3 or OCH 2 CH 3 ; and Y is F, Cl, Br, I, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , (CH 2 ) 3 CH 3 , CH 2 -CH=CH 2 , OCH 3 , OCH 2 CH 3 , CN, CH2CH2Cl, CH 2 CH 2 CH 2 Cl, CH 2 CH 2 OCH 3 , OCH 2 OCH 3 , CH 2 OCH 3 , OCH 2 CH 2 OCH 3 , CH 2 CO 2 R 6 , CH 2 CH 2 CO 2 R 6 , CO 2 R 6 , or NO; R is CH 3 or CH 2 CH 3 ; and their agriculturally suitable salts; provided that: 1) when is OCH 3 , then is CH 3 ; 2) when R 3 is OCH 3 , then R 4 is CH 3 ; and 3) when R is Cl, then Y is F.
Claim 3
Dependent Claim
20 words
A compound of Claim 1 wherein R is CO 2 R 2 or SO 2 NR 3 R 4 .
Claim 4
Dependent Claim
9 words
A compound of Claim 1 wherein R is H.
Claim 5
Dependent Claim
9 words
A compound of Claim 2 wherein R is H.
Claim 6
Dependent Claim
64 words
A compound of Claim 3 wherein R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl or C 2 -C 3 haloalkyl, and Y is F, Cl, Br, CH 3 , C 2 H 5 or CH 2 CH 2 C l , and at least one of X or Z is CH 3 , OCH 3 , ethyl or ethoxy.
Claim 7
Dependent Claim
33 words
A compound of Claim 5 wherein X is H, CH 3 or OCH 3 and Y is F, Cl, Br, CH 3 , C 2 H 5 or CH 2 CH 2 Cl.
Claim 8
Dependent Claim
8 words
Methyl 2-([(5-chloropyrimidin-2-yl) aminocarbonyl]aminosulfonyl)benzoate and its agriculturally suitable salts.
Claim 9
Dependent Claim
8 words
Methyl 2-([(5-chloropyrimidin-2-yl) aminocarbonyl]aminosulfonyl)benzoate and its agriculturally suitable salts.
Claim 10
Dependent Claim
9 words
. Methyl 2-([(4-chloro-6-methoxy-5-methyl- pyrimidin-2-yl)aminocarbonyl]aminosulfohyl)benzoate and its agriculturally suitable salts.
Claim 11
Dependent Claim
9 words
. Methyl 2-([(4-chloro-6-methoxy-5-methyl- pyrimidin-2-yl)aminocarbonyl]aminosulfohyl)benzoate and its agriculturally suitable salts.
Claim 12
Dependent Claim
7 words
Methyl 2-[[[4-chloro-5-(2-chloroethyl)-5-methylpyrimidin-2-yl]-aminocarbonyl)aminosulfonyl]-benzoate and its agriculturally suitable salts.
Claim 13
Dependent Claim
7 words
Methyl 2-[[[4-chloro-5-(2-chloroethyl)-5-methylpyrimidin-2-yl]-aminocarbonyl)aminosulfonyl]-benzoate and its agriculturally suitable salts.
Claim 14
Dependent Claim
7 words
Methyl 2-[[(4,5,6-trimethylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 15
Dependent Claim
7 words
Methyl 2-[[(4,5,6-trimethylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 16
Dependent Claim
8 words
Methyl 2-([(5-iodo-4,6-dimethylpyrimidin-2-yl) aminycarbonyl]-aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 17
Dependent Claim
8 words
Methyl 2-([(5-iodo-4,6-dimethylpyrimidin-2-yl) aminycarbonyl]-aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 18
Dependent Claim
7 words
Methyl 2-[[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 19
Dependent Claim
7 words
Methyl 2-[[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 20
Dependent Claim
7 words
Methyl 2-[[(5-bromo-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 21
Dependent Claim
7 words
Methyl 2-[[(5-bromo-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 22
Dependent Claim
7 words
Methyl 2-[[(5-ethyl-4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 23
Dependent Claim
7 words
Methyl 2-[[(5-ethyl-4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 24
Dependent Claim
6 words
2-Chloro-N-[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide and its agriculturally suitable salts.
Claim 25
Dependent Claim
6 words
2-Chloro-N-[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide and its agriculturally suitable salts.
Claim 26
Dependent Claim
7 words
Methyl 2-[[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 27
Dependent Claim
7 words
Methyl 2-[[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 28
Dependent Claim
8 words
(2-Propenyl 2-[[(5-fluoro-4,6-dimethoxy- pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 29
Dependent Claim
8 words
(2-Propenyl 2-[[(5-fluoro-4,6-dimethoxy- pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 30
Dependent Claim
7 words
Methyl 2-[[(5-chloro-4-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 31
Dependent Claim
7 words
Methyl 2-[[(5-chloro-4-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 32
Dependent Claim
7 words
Methyl 2-[[(5-ethyl-4-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 33
Dependent Claim
7 words
Methyl 2-[[(5-ethyl-4-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate and its agriculturally suitable salts.
Claim 34
Dependent Claim
42 words
A composition for the control of undesirable vegetation comprising a herbicidal compound and at least one of (a) a surface-active agent and (b) a solid or liquid diluent, characterised in that said herbicidal compound comprises a compound of any of claims 1-19.
Claim 35
Independent Claim
38 words
A method for the control of undesirable vegetation by applying to the locus of such undesirable vegetation an effective amount of a herbicidal compound, characterised in that said herbicidal compound comprises a compound of any of claims 1-19.
Claim 36
Independent Claim
42 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 1-19.
Claim 37
Dependent Claim
85 words
A process for making a compound of claim 1 which comprises reacting an isocyanate of general formula wherein R is CO 2 R 2 , SO 2 NR 3 R 4 , 2 Cl, CF 3 , NO 2 or S(O) n R 3 where n=O or 2 and R 1 , R , R , R 4 and B are as defined in claim 1, with an appropriately substituted 2-aminopyrimidine of general formula wherein X, Y and Z are as defined in claim 1.
Claim 38
Dependent Claim
134 words
Compounds of the general formula wherein A is R is CO 2 H; R 1 is H, Cl, F, Br, NO 2 , CH 3 , OCH 3 or CF 3 ; X and Z are independently H, CH 3 , Br, Cl, OCH 3 , CH 2 CH 3 , CH 2 OCH 3 or OCH2CH3; and Y is F, Cl, Br, I, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , (CH 2 ) 3 CH 3 , CH 2 -CH=CH 2 , OCH 3 , OCH 2 CH 3 , CN, CH 2 CH 2 Cl, CH 2 CH 2 OCH 3 , OCH 2 OCH 3 , CH 2 OCH 3 , OCH 2 CH2OCH 3 , or NO; and their agriculturally suitable salts.
Claim 39
Dependent Claim
134 words
Compounds of the general formula wherein A is R is CO 2 H; R 1 is H, Cl, F, Br, NO 2 , CH 3 , OCH 3 or CF 3 ; X and Z are independently H, CH 3 , Br, Cl, OCH 3 , CH 2 CH 3 , CH 2 OCH 3 or OCH2CH3; and Y is F, Cl, Br, I, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , (CH 2 ) 3 CH 3 , CH 2 -CH=CH 2 , OCH 3 , OCH 2 CH 3 , CN, CH 2 CH 2 Cl, CH 2 CH 2 OCH 3 , OCH 2 OCH 3 , CH 2 OCH 3 , OCH 2 CH2OCH 3 , or NO; and their agriculturally suitable salts.
References Cited (Backward Citations)
No citation records indexed.
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