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US 4,391,627 AGranted
Herbicidal benzothiophene and benzofuran sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorGeorge Levitt
Life of this patent
Estimating the term…
Abstract
Novel N-(heterocyclicaminocarbonyl)carbonyl-substituted benzothiophene- and benzofuransulfonamides are useful as herbicides. The invention also includes novel sulfonamides and sulfonyl isocyanates useful in preparing such compounds.
Claims35
A compound of the formula:
- ##STR102## wherein R is H or CH.sub.3 ;
- R.sup.1 is H, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, CO.sub.2 R.sup.2, C(O)NR.sup.3 R.sup.4, SO.sub.2 R.sup.5 or SO.sub.2 NR.sup.6 R.sup.7 ;
- R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 R.sup.8 ;
- R.sup.3 is C.sub.1 -C.sub.4 alkyl;
- R.sup.4 is H, C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ;
- or
- R.sup.3 and R.sup.4 can be taken together to form --(CH.sub.2).sub.4 --;
- R.sup.5 is C.sub.1 -C.sub.4 alkyl;
- R.sup.6 is C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ;
- R.sup.7 is C.sub.1 -C.sub.3 alkyl;
- R.sup.8 is C.sub.1 -C.sub.3 alkyl substituted with 1-3 atoms of F, Cl, or Br;
- R.sup.9 is H, CH.sub.3, OCH.sub.3, Cl, Br or NO.sub.2 ;
- W is O or S;
- A is ##STR103## X is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.3 or Cl;
- Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3 ;
- Z is N, CH, C--Cl, C--Br, C--CN, C--CH.sub.3, C--C.sub.2 H.sub.5, C--CH.sub.2 CH.sub.2 Cl or C--CH.sub.2 CH.dbd.CH.sub.2 ;
- Y.sup.1 is H, CH.sub.3, OCH.sub.3 or Cl;
- and
- Q is O or CH.sub.2 ;
- provided that
- (1) when R.sup.4 or R.sup.6 is OCH.sub.3, then R.sup.3 or R.sup.7 is CH.sub.3 ;
- (2) the total number of carbon atoms of either R.sup.3 and R.sup.4, or R.sup.6 and R.sup.7, is less than or equal to 4;
- and
- (3) when X is Cl, then Z is CH.
21 more elements
A compound selected from:
- ##STR105## R.sup.1 is H, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, CO.sub.2 R.sup.2, C(O)NR.sup.3 R.sup.4, SO.sub.2 R.sup.5 or SO.sub.2 NR.sup.6 R.sup.7 ;
- R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 R.sup.8 ;
- R.sup.3 is C.sub.1 -C.sub.4 alkyl;
- R.sup.4 is H, C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ;
- or
- R.sup.3 and R.sup.4 can be taken together to form --(CH.sub.2).sub.4 --;
- R.sup.5 is C.sub.1 -C.sub.4 alkyl;
- R.sup.6 is C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ;
- R.sup.7 is C.sub.1 -C.sub.3 alkyl;
- R.sup.8 is C.sub.1 -C.sub.3 alkyl substituted with, 1-3 atoms of F, Cl, or Br;
- R.sup.9 is H, CH.sub.3, OCH.sub.3, Cl, Br or NO.sub.2 ;
- W is O or S;
- and
- Z is N or CH.
11 more elements
A compound selected from:
- ##STR106## wherein M is H or alkali metal ion;
- R is H or CH.sub.3 ;
- R.sup.9 is H, CH.sub.3, OCH.sub.3, Cl, Br or NO.sub.2 ;
- W is O or S;
- A is ##STR107## X is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.3 ;
- Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3 ;
- Z is N, CH, C--Cl, C--Br, C--CN, C--CH.sub.3, C--C.sub.2 H.sub.5, C--CH.sub.2 CH.sub.2 Cl or C--CH.sub.2 CH.dbd.CH.sub.2 ;
- Y.sup.1 is H, CH.sub.3, OCH.sub.3 ;
- and
- Q is O or CH.sub.2.
7 more elements
Dependencies are inferred from the claim text.