EP0046677A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Herbicidal sulfonamides
Assignee: EIDP Inc
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Filing: 1981-08-21
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Granted: —
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Expires: 2001-08-21
Abstract
Abstract Compounds of the formula: (wherein A is an unsubstituted or substituted phenyl, phenoxy, pyridyl, furyl or thienyl group; W is 0 or S; X is CH 3 'C 2 H 5 , Cl, OCH 3 , OC 2 H 6 , N(CH 3 ) 2 or SCH 3 ; Y is H, CH 3 or C 2 H 5 and Z is H or CH 3 ) and the agriculturally suitable salts thereof possess herbicidal activity. They are also of interest as plant growth regulants and may be used to modify plant growth beneficially as well as to selectively control weeds in crops such as wheat, barley, cotton and soybeans. The compounds may be formulated for use in conventional manner. The compounds may be prepared by a variety of processes e.g. by reacting an appropriately substituted isocyanate or isothiocyanate with an appropriately substituted furo [2,3-d]pyrimidine amine. The furo [2,3-d] pyrimidine amines may be prepared by reaction of an appropriate keto-ester with guanidine carbonate or by reaction of an appropriate dichloropyrimidine with an alkali metal hydroxide. Compounds corresponding to formula I but in which A represents a benzyl, furyl or thienyl group substituted by a carboxyl or carboxylic acid salt moiety are novel intermediates.
Inventors
- 👤 William Thomas Zimmerman
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 20:10
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D239/46; C07D239/47; C07D239/52; C07D239/54; C07D239/545; C07D491/00; C07D491/02; C07D491/04; C07D521/00
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
783 words
A compound selected from where A is R is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 5 -C 6 cycloalkenyl, phenyl, phenyl substituted with one Cl or CH 3 group, C 1 -C 4 alkoxy, F, Cl, Br, NO 2 , NH 2 , CN, CF 3 , C(O)R 4 , S(O) m R 5 , SO 2 NR 6 R 7 , SO 2 N(DCH 3 )CH 3 , SO 2 OCH 2 CF 3 , SO 2 OCH 2 CCl 3 , BR 8 , OSO 2 R 9 , CH 2 L or CH(CH 3 )L; z is H or CH 3 ; R 1 is H, F, Cl, Br, CF 3 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy or NO 2 ; R 4 is H, C 1 -C 3 alkyl, C 1 -C 6 alkox y , benzyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 2 -C 6 haloalkoxy substituted with 1-3 atoms selected from F, Cl or Br, C 5 -C 6 cycloalkoxy, 0(CH 2 CH 2 O) n R 10 , OCH 2 CH 2 CH 2 OR 10 , OCH 2 OR 5 , OCH 2 OCH 2 CH 2 OR 10 , NR 11 R 12 or C 1 -C 4 alkylthio; m is 0, 1 or 2; n is 1 or 2; R 5 is C 1 -C 4 alkyl; R 6 and R 7 are independently C 1 -C 4 alkyl, provided that the total number of carbon atoms of R 6 and R 7 is less than or equal to 5; B is 0 or S(O) m ; R 8 is CHF 2 , CF 3 , CH 2 CF 3 or CF 2 CHFG where G is F, Cl, Br or CF 3 ; R 9 is C 1 -C 4 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OCH 3 , or C 1 -C 4 alkyl substituted with 1-3 atoms of F, Cl or Br; L is Cl, Br, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, OH, S(O) m R 5 , CO 2 R 17 or SO 2 N(CH 3 ) 2 ; R 10 is CH 3 or C 2 H 5 ; R 11 is H, C 1 -C 4 alkyl, OCH 3 or R 12 is H or C 1 -C 4 alkyl; R 11 and R 12 can also be taken together to form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -; n' is 0 or 1; R 13 is H, F, Cl, Br, NO 2 , CN, CF 3 , C 1 -C 3 alkyl, OCH 3 or SCH 3 ; R 14 is H , F, Cl, Br, CH 3 or OCH 3 ; R 2 is H , F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, NO 2 , CO 2 R 15 , S(O) m R 16 , SO 2 NR 18 R 19 or SO 2 N(OCH 3 )CH 3 ; R 15 is C 1 -C 4 alkyl; R 16 is C 1 -C 3 alkyl; R 17 is C 1 -C 4 alkyl, C 3 -C 4 alkenyloxy, CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 18 and R 19 are independently CH 3 or C 2 H 5 ; W' is 0 or S; R3 is C l -C 4 alkyl, C 1 -C 4 alkoxy, H, F, Cl, Br, NO 2 , SO 2 MR 6 R 7 , SO 2 N(OCH 3 )CH 3 or C(O)R 4 ; R 20 is F, Cl, Sr, CO 2 R 17 , OSO 2 R 9 , NO 2 , C 1 -C 4 alkyl or C 1 -C 4 alkoxy; W is 0 or S; X is CH 3 , C 2 H 5 , Cl, OCH 3 , OC 2 H 5 , N(CH 3 ) 2 or SCH 3 ; and Y is H, CH 3 or C 2 H 5 ; . and their agriculturally suitable salts; provided that (a) when R 11 is OCH 3 ; then R 12 is C H 3 ; (b) if R 1 is other than H and R is H, then R 1 cannot be in the 4-position of the benzene ring; (c) when R 11 is then R 12 is H or CH 3 ; and (d) when w' is 0, then R 3 is CO 2 R 17 .
Claim 2
Dependent Claim
783 words
A compound selected from where A is R is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 5 -C 6 cycloalkenyl, phenyl, phenyl substituted with one Cl or CH 3 group, C 1 -C 4 alkoxy, F, Cl, Br, NO 2 , NH 2 , CN, CF 3 , C(O)R 4 , S(O) m R 5 , SO 2 NR 6 R 7 , SO 2 N(DCH 3 )CH 3 , SO 2 OCH 2 CF 3 , SO 2 OCH 2 CCl 3 , BR 8 , OSO 2 R 9 , CH 2 L or CH(CH 3 )L; z is H or CH 3 ; R 1 is H, F, Cl, Br, CF 3 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy or NO 2 ; R 4 is H, C 1 -C 3 alkyl, C 1 -C 6 alkox y , benzyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 2 -C 6 haloalkoxy substituted with 1-3 atoms selected from F, Cl or Br, C 5 -C 6 cycloalkoxy, 0(CH 2 CH 2 O) n R 10 , OCH 2 CH 2 CH 2 OR 10 , OCH 2 OR 5 , OCH 2 OCH 2 CH 2 OR 10 , NR 11 R 12 or C 1 -C 4 alkylthio; m is 0, 1 or 2; n is 1 or 2; R 5 is C 1 -C 4 alkyl; R 6 and R 7 are independently C 1 -C 4 alkyl, provided that the total number of carbon atoms of R 6 and R 7 is less than or equal to 5; B is 0 or S(O) m ; R 8 is CHF 2 , CF 3 , CH 2 CF 3 or CF 2 CHFG where G is F, Cl, Br or CF 3 ; R 9 is C 1 -C 4 alkyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OCH 3 , or C 1 -C 4 alkyl substituted with 1-3 atoms of F, Cl or Br; L is Cl, Br, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, OH, S(O) m R 5 , CO 2 R 17 or SO 2 N(CH 3 ) 2 ; R 10 is CH 3 or C 2 H 5 ; R 11 is H, C 1 -C 4 alkyl, OCH 3 or R 12 is H or C 1 -C 4 alkyl; R 11 and R 12 can also be taken together to form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -; n' is 0 or 1; R 13 is H, F, Cl, Br, NO 2 , CN, CF 3 , C 1 -C 3 alkyl, OCH 3 or SCH 3 ; R 14 is H , F, Cl, Br, CH 3 or OCH 3 ; R 2 is H , F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, NO 2 , CO 2 R 15 , S(O) m R 16 , SO 2 NR 18 R 19 or SO 2 N(OCH 3 )CH 3 ; R 15 is C 1 -C 4 alkyl; R 16 is C 1 -C 3 alkyl; R 17 is C 1 -C 4 alkyl, C 3 -C 4 alkenyloxy, CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 18 and R 19 are independently CH 3 or C 2 H 5 ; W' is 0 or S; R3 is C l -C 4 alkyl, C 1 -C 4 alkoxy, H, F, Cl, Br, NO 2 , SO 2 MR 6 R 7 , SO 2 N(OCH 3 )CH 3 or C(O)R 4 ; R 20 is F, Cl, Sr, CO 2 R 17 , OSO 2 R 9 , NO 2 , C 1 -C 4 alkyl or C 1 -C 4 alkoxy; W is 0 or S; X is CH 3 , C 2 H 5 , Cl, OCH 3 , OC 2 H 5 , N(CH 3 ) 2 or SCH 3 ; and Y is H, CH 3 or C 2 H 5 ; . and their agriculturally suitable salts; provided that (a) when R 11 is OCH 3 ; then R 12 is C H 3 ; (b) if R 1 is other than H and R is H, then R 1 cannot be in the 4-position of the benzene ring; (c) when R 11 is then R 12 is H or CH 3 ; and (d) when w' is 0, then R 3 is CO 2 R 17 .
Claim 3
Dependent Claim
27 words
A compound of Claim 1 where w is 0; Y is CH 3 ; X is other than Cl; A is other than and Z is H.
Claim 4
Dependent Claim
17 words
A compound of Clain 2' where X is CH 3 or OCH 3 ; and A is
Claim 5
Dependent Claim
17 words
A compound of Clain 2' where X is CH 3 or OCH 3 ; and A is
Claim 6
Dependent Claim
17 words
A compound. of Claim 2 where X is CH 3 or OCH 3 ; and A is
Claim 7
Dependent Claim
18 words
A compound of Claim 2 where X is C H 3 or OCH 3 ; and A is
Claim 8
Dependent Claim
208 words
A compound of Claim 3 where R is C 1 -C 3 alkyl, OCH 3 , F, Cl, Br, NO 2 , CF 3 , C(O)R 4 , S(O) m R 5 , SO 2 NR 6 R 7 , SO 2 N(OCH 3 )CH 3 , BR 8 , OSO 2 R 9 or CH 2L ; R 4 is H, C 1 -C 3 alkyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, haloethoxy containing 1-3 atoms of F or Cl, OCH 2 CH 2 OR 10 , OCH 2 CH 2 CH 2 OR 10 , OCH 2 OR 5 , OCH 2 OCH 2 CH 2 OR 10 , NR 11 R 12 or C 1 -C 4 alkylthio; B is 0; L is.OCH 3 or CO 2 R 17 ; R 11 is C 1 -C 4 alkyl or OCH 3 ; R 12 is C 1 -C 4 alkyl; and R 11 and R 12 can be taken together to form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -, provided that the total carbon atoms of R 11 and R 12 is less than or equal to 5.
Claim 9
Dependent Claim
66 words
A compound of Claim 6 where R 1 is H; R 4 is C I -C 4 alkox y, C 3 - C 4 alkenyloxy, OCH 2 CH 2 Cl or OCH 2 CH 2 OCH 3 ; R 8 is CF 3 , CH 2 CF 3 or CF 2 CHF 2 ; R 9 is CH 3 ; and L is OCH 3 .
Claim 10
Dependent Claim
43 words
A compound of Claim 7 where R is NO 2 , C(O)R 4 , SO 2 R 5 or SO 2 N(CH 3 ) 2 ; R 4 is C 1 -C 3 alkoxy; and R 5 is C 1 -C 3 alkyl
Claim 11
Dependent Claim
25 words
A compound of Claim 4 where A is and R 2 is Cl, Br, CH 3 , OCH 3 or S(O) m CH 3 .
Claim 12
Dependent Claim
32 words
A compound of Claim 5 where - W' is S; R 3 is H, CH 3 , Cl, Br or C(O)R 4 ; and R 4 is C l -C 3 alkoxy.
Claim 13
Dependent Claim
12 words
The compound of Claim 1, 2-chloro-N-[(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]benzenesulfonamide and the agriculturally suitable salts thereof.
Claim 14
Dependent Claim
13 words
The compound of Claim 1, N-[(4,6-dimethyl- furo[2,3-d]py'rimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide and the agriculturally suitable salts' thereof.
Claim 15
Dependent Claim
19 words
13 . The compound of Claim 1, 2-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl benzolc acid, methyl ester and the agriculturally suitable salts thereof.
Claim 16
Dependent Claim
16 words
The compound of Claim 1, 2-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl benzoic acid, (2-propenyl)ester and the agriculturally suitable salts thereof.
Claim 17
Dependent Claim
16 words
The compound of Claim 1, 2-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl benzoic acid, (1-methylethyl)ester and the agriculturally suitable salts thereof.
Claim 18
Dependent Claim
12 words
The compound of Claim 1, 2-chloro-N-[(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide and the agriculturally suitable salts thereof.
Claim 19
Dependent Claim
15 words
The compound of Claim 1, 3-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-thiophenecarboxylate, methyl ester and the agriculturally suitable salts thereof.
Claim 20
Dependent Claim
15 words
18 . The compound of Claim 1, N-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]-3-methyl-2-thiophenesulfonamide and the agriculturally suitable salts thereof.
Claim 21
Dependent Claim
19 words
1 9 . The compound of Claim 1, 4-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl-3-thiophenecarboxylate, methyl ester and the agricult- .urally suitable salts thereof.
Claim 22
Dependent Claim
16 words
The compound of Claim 1, 2-[[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyll- benzoic acid, ethyl ester.and the agriculturally suitable salts thereof.
Claim 23
Dependent Claim
15 words
The compound of Claim 1, 2-[[(4-methoxy-6-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester and the agriculturally suitable salts thereof.
Claim 24
Dependent Claim
14 words
The compound of Claim 1, N-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminobarbonyl]-2-methylsul- fonylbenzenesulfonamide and the agriculturally suitable salts thereof.
Claim 25
Dependent Claim
13 words
The compound of Claim 1, N'-[(4,6-dimethyl- furo[2,3-d]pyrimidin-2-yl)aminocarbonyl]-N,N-dimethylbenzene-1,2-sulfonamide and the agriculturally suitable salts thereof.
Claim 26
Dependent Claim
498 words
A process for the preparation of a compound as claimed in claim 1 which comprises:- a) reacting a compound of the formula:. (wherein A and W are as defined in claim 1 with the proviso that R is other than NH 2 , CN, S(O)R 5 , CH 2 0H, CH 2 S (O) R 5 , CH(CH 3 )OH, CH(CH 3 )S (O) R 5 , R 2 is other than S(O)R 16 and R 4 is other than H, C 1-3 alkyl, OCH 2 OR 5 , C 3-6 alkynyloxy, -OCH 2 OCH 2 CH 2 OR 10 , -NR 11 R 12 or C 1-4 alkylthio) with a compound of the formula: (wherein X, Y and Z are as defined in claim 1); b) for the preparation of a compound of formula I wherein R or R 3 is -COR 4 (wherein R 4 is alkylthio or secondary,alkoxy), the reaction of the corresponding methyl ester with an alkanethiol or a secondary alkanol in the presence of trialkyl aluminum compound; c) for the preparation of a compound of formula I (wherein R is CO R 4 and R 4 is NR 11 R 12 as defined in claim 1) the reaction of the corresponding methyl ester with an appropriate dialkylaluminum amide; d) for the preparation of compounds of formula I wherein A represents the group wherein R is C 1-3 alkyl and R 1 and W' are as defined in'claim 1, the reaction of the corresponding carboxylic acid with the compound of the formula R 4 Li wherein R 4 is C 1-3 alkyl; e) for the preparation of compounds of formula I (wherein A is substituted by -CHO, R 1 being other than -NO 2 ), the reaction of the corresponding alkyl ester with a complex aluminum hydride; f) for the preparation of compounds of formula I wherein A is the reaction of a compound of formula I in which A represents with 2-nitropropane in the presence of a base; g) for the preparation of compounds of formula I wherein A represents substituted by CO 2 R 4' , the reaction of a corresponding carboxylic acid or salt thereof with an appropriate compound of the formula R - halogen; - h) for the preparation of a compound of formula I (wherein A is the selective reduction of the corresponding compound of formula I in which A is i) for the preparation of a compound of formula I in which A is the reaction of the corresponding compound of formula I in which A is with a copper cyanide; j) for the preparation of a compound of formula I wherein A is the selective reduction of a corresponding compound of formula I in which A is k) for the preparation of a compound of formula I wherein A is m is 1 or 2 and R 5 is as defined in claim 1, the oxidation of a corresponding compound of formula I in which A is.
Claim 27
Dependent Claim
61 words
A composition suitable for controlling the growth of undesired vegetation or for use as a plant growth regulant which comprises an effective amount of a herbicidal compound or plant growth regulant and at least one of the following: surfactant, solid or liquid diluent, characterised in that said herbicidal compound or plant growth regulant comprises a compound of any of claims 1-23.
Claim 28
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 23.
Claim 29
Independent Claim
44 words
A method for regulating the growth of plants by applying to the locus of said 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 23.
Claim 30
Dependent Claim
73 words
A-compound selected from or wherein R 1 is H, F, Cl, Br, CF 3 , C 1 -C 4 alkyl or C 1 -C 4 alkoxy; M is H or an alkali metal; W' is 0 or S; w is 0 or S; X is CH 3 , C 2 H 5 , OCH 3 or OC 2 H 5 ; and Y is H, CH 3 or C 2 H 5 .
Claim 31
Dependent Claim
73 words
A-compound selected from or wherein R 1 is H, F, Cl, Br, CF 3 , C 1 -C 4 alkyl or C 1 -C 4 alkoxy; M is H or an alkali metal; W' is 0 or S; w is 0 or S; X is CH 3 , C 2 H 5 , OCH 3 or OC 2 H 5 ; and Y is H, CH 3 or C 2 H 5 .
Claim 32
Dependent Claim
67 words
A process for preparing a compound of general formula wherein X and Y are independently CH 3 or C 2 H 5 ; which comprises reacting a keto-ester of the formula wherein Y 1 is H or CH 3 ; with an excess of guanidine carbonate in a polar aprotic solvent at a temperature in the range of about 80° to 200° and isolating the reaction product.
Claim 33
Dependent Claim
67 words
A process for preparing a compound of general formula wherein X and Y are independently CH 3 or C 2 H 5 ; which comprises reacting a keto-ester of the formula wherein Y 1 is H or CH 3 ; with an excess of guanidine carbonate in a polar aprotic solvent at a temperature in the range of about 80° to 200° and isolating the reaction product.
Claim 34
Dependent Claim
44 words
A process for preparing a compound of the general formula wherein Y is CH 3 or C 2 H 5 ; which comprises reacting a dichloropyrimidine of the formula wherein Y 1 is H or C H 3 ; with an alkali metal hydroxide.
Claim 35
Dependent Claim
44 words
A process for preparing a compound of the general formula wherein Y is CH 3 or C 2 H 5 ; which comprises reacting a dichloropyrimidine of the formula wherein Y 1 is H or C H 3 ; with an alkali metal hydroxide.
References Cited (Backward Citations)
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