EP0085476A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Herbicidal sulfonamides
Assignee: EIDP Inc
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Filing: 1983-01-07
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Granted: —
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Expires: 2003-01-07
Abstract
Abstract Sulfonamide derivatives of formulae wherein Q is selected from various 5 and 6-membered heterocyclic groups, which are optionally substituted, Q' is selected from various 6-membered nitrogen- containing heterocyclic groups, which are optionally substituted, R, is H, F, Cl, Br, CH 3 , CF 3 or OCH 3 , R 17 is H or CH 3 , W is O or S, A is a substituted heterocyclic moiety, X is CH 3 , OCH 3 or Cl, Y is amino or various organic groups, Z is CH or H: and their agriculturally suitable salts exhibit herbicidal and plant growth regulant effects. The compounds may be formulated for agricultural use in conventional manner. The compounds may be prepared by a variety of routes, e.g. by reacting an appropriately substituted benzenesulfonamide having a Q or Q' moiety in the 2-position with a methyl carbamate of the appropriate heterocyclic amine, under catalytic conditions.
Inventors
- 👤 Richard Frank Sauers
- 👤 Rafael Shapiro
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 09:03
CPC Classifications
C; C07; C07D; C07D521/00; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/32; C07D213/34; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
623 words
A compound of the formula: wherein Q is where Q' is W is 0 or S; W' is 0 or S; R is H, F, Cl, CH 3 or OCH 3 ; R 1 is H, F, C 1 , Br, CH 3 , CF 3 or OCH 3 ; R 2 , R 3 , R 5 , R 9 , R 10 , R 11 , R 12 and R 17 are independently H or CH 3 ; R 4 , R 6 , R 7 and R 8 are independently H, CH 3 or OCH3; R 13 , R 14 , R 15 and R 16 are independently CH 3 or OC H 3 ; R 18 is H or CH 3 ; R 19 is H or CH 3 ; R 20 is H or CH 3 ; R 21 is H or CH 3 ; R 22 is H or CH 3 ; R 23 is H or CH 3 ; R 24 is H, CH 3 , C 2 H 5 , Cl, Br, OCH 3 or OC 2 H 5 ; R25 is H , CH 3 , C 2 H 5 , Cl, Br, OCH 3 or OC 2 H 5 ; R26 is H, CH 3 , C 2 H 5 , Cl, Br, OCH 3 , OC 2 H 5 or CO 2 CH 3 ; R27 is H or C H 3 ; R28 is H or CH 3 ; A is 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 , CH(OCH 3 ) 2 , SCH 2 , CF 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , OCH 2 CH 2 OCH 3 , OCH 2 CF 3 or Y 1 is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , CH(OCH 3 ) 2 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; Z is CH or N; - X 1 is CH 3 , OCH 3 or Cl; G is 0 or CH 2 ; X 2 is C 1 -C 3 alkyl or CH 2 CF 3 ; Y 2 is CH 3 0, C 2 H 5 O, CH 3 S or C 2 H 5 S; and their agriculturally suitable salts; provided that 1) when W is S, then R 17 is H, A is Y is CH 3 , OCH 3 , C 2 H 5 , CH 2 OCH 3 , CH(OCH 3 ) 2 or 2) when Q is then R 24 is H, CH 3 or C 2 H 5 ; R 25 is H, CH 3 or C 2 H 5 ; and R 26 is H, CH 3 , C 2 H 5 or -CO 2 CH 3 ; 3) when one of R 24 , R 25' R 26 is other than H, then the other two substituents are H or C H 3 ; 4) the total number of carbon atoms in R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 27 and R 28 is less than or equal to 4; 5) when X is Cl, then Z is CH and Y or Y 1 is OCH 3 , NH 2 , OC 2 H 5 , NHCH 3 or N(CH 3 ) 2 ; and 6) when R is CH3, then R is in the 3-, 4- or 5-position of the benzene ring.
Claim 2
Dependent Claim
623 words
A compound of the formula: wherein Q is where Q' is W is 0 or S; W' is 0 or S; R is H, F, Cl, CH 3 or OCH 3 ; R 1 is H, F, C 1 , Br, CH 3 , CF 3 or OCH 3 ; R 2 , R 3 , R 5 , R 9 , R 10 , R 11 , R 12 and R 17 are independently H or CH 3 ; R 4 , R 6 , R 7 and R 8 are independently H, CH 3 or OCH3; R 13 , R 14 , R 15 and R 16 are independently CH 3 or OC H 3 ; R 18 is H or CH 3 ; R 19 is H or CH 3 ; R 20 is H or CH 3 ; R 21 is H or CH 3 ; R 22 is H or CH 3 ; R 23 is H or CH 3 ; R 24 is H, CH 3 , C 2 H 5 , Cl, Br, OCH 3 or OC 2 H 5 ; R25 is H , CH 3 , C 2 H 5 , Cl, Br, OCH 3 or OC 2 H 5 ; R26 is H, CH 3 , C 2 H 5 , Cl, Br, OCH 3 , OC 2 H 5 or CO 2 CH 3 ; R27 is H or C H 3 ; R28 is H or CH 3 ; A is 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 , CH(OCH 3 ) 2 , SCH 2 , CF 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , OCH 2 CH 2 OCH 3 , OCH 2 CF 3 or Y 1 is CH 3 , C 2 H 5 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , CH(OCH 3 ) 2 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; Z is CH or N; - X 1 is CH 3 , OCH 3 or Cl; G is 0 or CH 2 ; X 2 is C 1 -C 3 alkyl or CH 2 CF 3 ; Y 2 is CH 3 0, C 2 H 5 O, CH 3 S or C 2 H 5 S; and their agriculturally suitable salts; provided that 1) when W is S, then R 17 is H, A is Y is CH 3 , OCH 3 , C 2 H 5 , CH 2 OCH 3 , CH(OCH 3 ) 2 or 2) when Q is then R 24 is H, CH 3 or C 2 H 5 ; R 25 is H, CH 3 or C 2 H 5 ; and R 26 is H, CH 3 , C 2 H 5 or -CO 2 CH 3 ; 3) when one of R 24 , R 25' R 26 is other than H, then the other two substituents are H or C H 3 ; 4) the total number of carbon atoms in R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 27 and R 28 is less than or equal to 4; 5) when X is Cl, then Z is CH and Y or Y 1 is OCH 3 , NH 2 , OC 2 H 5 , NHCH 3 or N(CH 3 ) 2 ; and 6) when R is CH3, then R is in the 3-, 4- or 5-position of the benzene ring.
Claim 3
Dependent Claim
10 words
Compounds of Claim 1, Formula I, where W is 0.
Claim 4
Dependent Claim
12 words
Compounds of Claim 2 where R 1 and R 17 are H.
Claim 5
Dependent Claim
47 words
Compounds of Claim 3 where R 24 is H, CH \3 or C 2 H 5 ; R25 is H , CH 3 or C 2 H 5 ; and R 26 is H, CH 3 , C 2 H 5 or -CO 2 CH 3 ;
Claim 6
Dependent Claim
31 words
Compounds of Claim 4 where Y is CH 3 , CH 2 OCH 3 , OCH 3 , OC 2 H 5 , CH(OCH 3 ) 2 or and A is
Claim 7
Dependent Claim
13 words
Compounds of Claim 1, Formula Ia, where R and R 17 are H.
Claim 8
Dependent Claim
22 words
Compounds of Claim 6 where Y 1 is CH 3 , OCH 3 , CH 2 0CH 3 or N(CH 3 )2.
Claim 9
Dependent Claim
8 words
Compounds of Claim 4 where W' = 0.
Claim 10
Dependent Claim
8 words
Compounds of Claim 4 where W' = S.
Claim 11
Dependent Claim
10 words
Compounds of Claim 7 where Q' is a substituted pyridine.
Claim 12
Dependent Claim
10 words
Compounds of Claim 7 where Q' is a substituted pyrimidine.
Claim 13
Dependent Claim
10 words
Compounds of Claim 7 where Q' is a substituted pyrazine.
Claim 14
Dependent Claim
10 words
Compounds of Claim 7 where Q' is a substituted triazine.
Claim 15
Dependent Claim
23 words
A mpound of Claim 1 selected from N- . [(4,6-dimethylpyrimidin-2-yl)aminocarbonyl[-2-(tetrahydrofuran-2-yl]benzenesulfonamide; N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl))benzenesulfonamide; N-[-(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-1-(tetrahydrofuran-2-yl]benzenesulfonamide; N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl]benzenesulfonamide; N -[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide; N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl)-2-(tetrahydrofuran-2-yl)benzenesulfonamide; or an agriculturally suitable salt thereof.
Claim 16
Dependent Claim
16 words
A compound of Claim 1 selected from N-[(4-methoxy-6-methylpyrimidin-2-yl]aminocarbonyl)-2-(2-pyridinyl)benzenesulfonamide; N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(2-pyridinyl]benzenesulfonamide; N-[C4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-2-(2-pyridinyl)benzenesulfonamide; or an agriculturally suitable salt thereof.
Claim 17
Dependent Claim
16 words
. A compound of Claim 1 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(2-pyrimidinyl) benzenesulfonamide; or an agriculturally suitable salt thereof.
Claim 18
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 16.
Claim 19
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 16.
Claim 20
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 16.
Claim 21
Dependent Claim
168 words
A method for the preparation of a compound of . claim 1 which comprises (a) reacting a benzenesulfonamide of formula I with a methyl heteroaryl carbamate of formula under catalytic conditions, to obtain a compound of formula (I) wherein R 1 , R 17 , Q and A are as defined in claim 1 and W is 0; or (b) reacting a benzenesulfonyl isocyanate or isothiocyanate of formula with an aminoheterocycle of formula wherein R 1 , R 17 , W and A are as defined in claim 1 and Q is selected from Q-1, Q-2 or Q-6 to Q-11; or (c) reacting said sulfonamide of formula (II) with a heterocyclic isothiocyanate of formula wherein A is as defined in claim 1; or (dl reacting a sulfonamide of formula with a methyl pyrimidinyl carbamate or methyl triazinyl carbamate of formula under catalytic conditions, wherein R 1 , R 17 , Q', X, Y and Z are as defined in claim 1, to obtain a product of formula (Ia).
References Cited (Backward Citations)
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