Pyridylsulfonylureas as herbicides and plant growth regulators, processes for their preparation and their use
AssigneeHoechst Schering AgrEvo GmbH
InventorsHeinz Kehne, Lothar Willms, Oswald Ort, Klaus Bauer, Hermann Bieringer
Life of this patent
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Abstract
Compounds of formula (I), where R.sup.1, R.sup.2, n, W, R.sup.3 and A are as defined in claim 1, are suitable for use as herbicides and plant growth regulators. They can be produced by a process similar to known processes. To produce them, new compounds of formula (II) are reacted with a carbamate of formula R*--O--CO--NR.sup.3 A, where R.sup.3 stands for phenyl or alkyl. The compounds of formula (II) can be obtained from the corresponding sulphochlorides.
Claims90
A compound of the formula (I) or its salts ##STR75## in which R.sup.2 is H, a (C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.3)haloalkyl group, halogen, a (C.sub.1 -C.sub.3)alkoxy group, a (C.sub.1 -C.sub.3)alkylthio group, a (C.sub.1 -C.sub.3)alkoxy-(C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.3)alkylamino group or a di[(C.sub.1 -C.sub.3)alkyl]amino group,
- R.sup.6 is H, a (C.sub.1 -C.sub.4)alkyl group, or a (C.sub.3 -C.sub.4)alkenyl group,
- R.sup.7 is (C.sub.1 -C.sub.4)alkylsulfonyl,
- X is halogen, a (C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.3)alkoxy group or a (C.sub.1 -C.sub.3)haloalkoxy group, and
- Y is a (C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.3)alkoxy group or a (C.sub.1 -C.sub.3)haloalkoxy group.
The herbicidal composition according to claim 5 or 16 wherein the proportion of the compound of the formula (I) or its salt to the agricultural adjuvant is within a range of from 0.1:99 to 990:10.
A compound of the formula:
- ##STR76## wherein R.sup.1 is --NHSO.sub.2 CH.sub.3 ;
- R.sup.2 is H, 4--CH.sub.3, 6--CH.sub.3, 4--Cl, 6--Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, Cl or --CH.sub.3 ;
- and Z is CH.
A compound of the formula:
- ##STR77## wherein R.sup.1 is --NHSO.sub.2 C.sub.2 H.sub.5 ;
- R.sup.2 is H, 4--CH.sub.3, 6--CH.sub.3, 4--Cl, 6--Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, --CH.sub.3 or Cl;
- and Z is CH.
A compound of the formula:
- ##STR78## wherein R.sup.1 is --NHSO.sub.2 C.sub.3 H.sub.7 ;
- R.sup.2 is H, 4--CH.sub.3, 6-CH.sub.3, 4--Cl, 6--Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, --CH.sub.3 or Cl;
- and Z is CH.
A compound of the formula:
- ##STR79## wherein R.sup.1 is --N(CH.sub.3)SO.sub.2 CH.sub.3 ;
- R.sup.2 is H, 4--CH.sub.3, 6--CH.sub.3, 4--Cl, 6--Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, --CH.sub.3 or Cl;
- and Z is CH.
A compound of the formula:
- ##STR80## wherein R.sup.1 is --N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 ;
- R.sup.2 is H, 4--CH.sub.3, 6--CH.sub.3, 4--Cl, 6Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, --CH.sub.3 or Cl;
- and Z is CH.
A compound of the formula:
- ##STR81## wherein R.sup.1 is --N(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3 ;
- R.sup.2 is H, 4--CH.sub.3, 6--CH.sub.3, 4--Cl, 6--Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, --CH.sub.3 or Cl;
- and Z is CH.
A compound of the formula:
- ##STR82## wherein R.sup.1 is --N(C.sub.3 H.sub.7)SO.sub.2 CH.sub.3 ;
- R.sup.2 is H, 4--CH.sub.3, 6--CH.sub.3, 4--Cl, 6--Cl, 6--F or 6--OCH.sub.3 ;
- R.sup.3 is H;
- X is --OCH.sub.3 or --CH.sub.3 ;
- Y is --OCH.sub.3, --CH.sub.3 or Cl;
- and Z is CH.
A compound of formula (I):
- ##STR83## in which:
- R.sup.1 is NR.sup.6 R.sup.7,
- Z is CH, and:
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl, X is methoxy, Y is methoxy;
- or
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl, X is methoxy, Y is methyl;
- or
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl, X is methyl, Y is methyl;
- or
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is ethyl, R.sup.7 is methylsulfonyl, X is methoxy, Y is methoxy;
- or
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is ethylsulfonyl, X is methoxy, Y is methoxy;
- or
- R.sup.2 H, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl X is chlorine and Y is methoxy;
- or
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is H, R.sup.7 is methylsulfonyl and each of X and Y is methoxy;
- or
- R.sup.2 is 6--CH.sub.3, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl and each of X and Y is methoxy;
- or
- R.sup.2 is 6--OCH.sub.3, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl and each of X and Y is methoxy;
- or
- R.sup.2 is 6--Cl, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl and each of X and Y is methoxy;
- or
- R.sup.2 is 6--F, R.sup.3 is H, R.sup.6 is methyl, R.sup.7 is methylsulfonyl and each of X and Y is methoxy;
- or
- R.sup.2 is H, R.sup.3 is H, R.sup.6 is ethyl, R.sup.7 is methylsulfonyl, and each of X and Y is methyl.
A compound of the formula or its salts:
- ##STR84## wherein R.sup.1 is --NHSO.sub.2 CH.sub.3, --NHSO.sub.2 C.sub.2 H.sub.5, --NHSO.sub.2 C.sub.3 H.sub.7, --N(CH.sub.3)SO.sub.2 CH.sub.3, --N(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3, --N(C.sub.3 H.sub.7)SO.sub.2 CH.sub.3, or --N(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5 ;
- R.sup.2 is H, methyl, chlorine, fluorine, or methoxy;
- R.sup.3 is H;
- X is methoxy or methyl;
- Y is methoxy, chlorine or methyl;
- and
- Z is CH.
Dependencies are inferred from the claim text.