Cyclic sulfonamide herbicides

Details Cyclic sulfonamide herbicides Cyclic sulfonamide herbicides

1996-11-13

1998-05-12

Richter, Johann

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548207, A01N 4380, C07D41704

Patent

active

057504717

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/US95/06706 filed Jun. 2, 1995.


BACKGROUND OF THE INVENTION

This invention relates to certain cyclic sulfonamides, their agriculturally-suitable salts and compositions, and methods of their use as general or selective preemergent or postemergent herbicides.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat, citrus and soybeans, to name a few. Unchecked weed growth in such crops (including plantation crops) can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,818,275 discloses herbicidal acyclic sulfonamides of the formula ##STR1## wherein, inter alia X and Y are Br; Cl; or F; the formula ##STR2## wherein X is H or halogen; alkyl, C.sub.1 -C.sub.6 haloalkyl, or CO.sub.2 R.sub.a ; alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.8 cycloalkyl, --COR.sub.b, --CO.sub.2 R.sub.b, or --CH.sub.2 CO.sub.2 R.sub.b ; ##STR3## Q is N or CH; E is O or S; is N; or C.sub.4 alkylene which combines with Q to form a 6-membered ring when Q is CH; is N; or C.sub.4 alkylene which combines with Q to form a 6-membered ring when Q is CH; and
The cyclic sulfonamides of the present invention are not disclosed in either of these references.


SUMMARY OF THE INVENTION

This invention includes compounds of Formulae I and II including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation: ##STR4## wherein X is a direct bond; O; S; NH; N(C.sub.1 -C.sub.3 alkyl); N(C.sub.1 -C.sub.3 haloalkyl); or N(allyl); -C.sub.8 alkenyl; C.sub.3 -C.sub.8 alkynyl; C.sub.1 -C.sub.8 haloalkyl; C.sub.2 -C.sub.8 alkoxyalkyl; C.sub.3 -C.sub.8 alkoxyalkoxyalkyl; C.sub.3 -C.sub.8 haloalkynyl; C.sub.3 -C.sub.8 haloalkenyl; C.sub.1 -C.sub.8 alkylsulfonyl; C.sub.1 -C.sub.8 haloalkylsulfonyl; C.sub.3 -C.sub.8 alkoxycarbonylalkyl; S(O).sub.2 NH(C.sub.1 -C.sub.8 alkyl); C(O)R.sup.6 ; or benzyl optionally substituted on the phenyl ring with R.sup.7 ; S(O).sub.2 (C.sub.1 -C.sub.6 alkyl); or C(.dbd.O)R.sup.8 ; or are attached to form a spiro-cyclopropane ring; -C.sub.6 alkoxy; NH(C.sub.1 -C.sub.6 alkyl); phenyl optionally substituted with R.sup.7 ; benzyl; or C.sub.2 -C.sub.8 dialkylamino; CF.sub.3 ; NH(C.sub.1 -C.sub.6 alkyl); ##STR5## wherein the dashed line in J-5, J-6 and J-12 indicates that the left-hand ring contains only single bonds or one bond in the ring is a carbon-carbon double bond; alkyl); C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkylcarbonyloxy; or C.sub.2 -C.sub.6 haloalkylcarbonyloxy; halogen; alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.1 -C.sub.6 haloalkyl; -C.sub.6 alkenyl; C.sub.3 -C.sub.6 haloalkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.6 haloalkynyl; HC(.dbd.O); (C.sub.1 -C.sub.4 alkyl)C(.dbd.O); or NH.sub.2 ; -C.sub.6 haloalkyl; CF.sub.3 ; or N(CH.sub.3).sub.2 substituted with C.sub.1 -C.sub.6 alkyl, 1-2 halogen, C.sub.1 -C.sub.6 alkoxy, or CF.sub.3 ; -C.sub.4 alkyl); alkoxy; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 haloalkoxy; C.sub.2 -C.sub.6 alkylcarbonyloxy; or C.sub.2 -C.sub.6 haloalkylcarbonyloxy; together with the carbons to which they are attached to form ##STR6## R.sup.18 is C.sub.1 -C.sub.6 alkyl; halogen; or C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3

REFERENCES:
patent: 4906281 (1990-03-01), Chang
Chemical Abstracts, vol. 110, No. 23, Jun. 5,1989, Columbus, OH abstract No. 212837t, p.756.

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