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 ##STR2## wherein, inter alia X and Y are Br; Cl; or F;
R is alkyl; haloalkyl; or dialkylamino; and PA1 R.sup.1 is H; Na; lower alkyl; or SO.sub.2 R. PA1 JP 631988!-222167 discloses herbicidal cyclic amides and sulfonamides of the formula ##STR3## wherein X is H or halogen; PA1 Z is O or S; PA1 J is, inter alia, --CO-- or --SO.sub.2-- ; PA1 L.sub.1 is --CO-- or --CR.sub.4 (R.sub.5)--; PA1 R.sub.4 and R.sub.5 are each independently, inter alia, H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, or CO.sub.2 R.sub.a ; PA1 R.sub.1 is, inter alia, H, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.1 -C.sub.6 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 ; PA1 W is, inter alia, ##STR4## Q is N or CH; E is O or S; PA1 R.sub.12 is H, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl when Q is N; or PA1 R.sub.12 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, or C.sub.4 alkylene which combines with Q to form a 6-membered ring when Q is CH; PA1 R.sub.13 is H, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 haloalkyl when Q is N; or PA1 R.sub.13 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, or C.sub.4 alkylene which combines with Q to form a 6-membered ring when Q is CH; and PA1 m is 0 or 1. PA1 R.sup.1 is H; F; Cl; or Br; PA1 R.sup.2 is H; F; Cl; Br; CF.sub.3 ; nitro; or cyano; PA1 R.sup.3 is H; C.sub.1 -C.sub.8 alkyl; C.sub.3 -C.sub.8 cycloalkyl; C.sub.3 -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 ; PA1 R.sup.4 is H; C.sub.1 -C.sub.3 alkyl; or halogen; PA1 R.sup.5 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; halogen; S(O).sub.2 (C.sub.1 -C.sub.6 alkyl); or C(.dbd.O)R.sup.8 ; or PA1 R.sup.4 and R.sup.5 are taken together along with the carbon to which they are attached to form a spiro-cyclopropane ring; PA1 R.sup.6 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.1 -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 dialkylamnino; PA1 R.sup.7 is C.sub.1 -C.sub.6 alkyl; 1-2 halogen; C.sub.1 -C.sub.6 alkoxy; or CF.sub.3 ; PA1 R.sup.8 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkoxy; or NH(C.sub.1 -C.sub.6 alkyl); PA1 J is ##STR6## 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; PA1 n and m are each independently 0; 1; 2; or 3; provided that m+n is 2 or 3; PA1 Z is CR.sup.9 R.sup.10 ; O; S; S(O); S(O).sub.2 ; N(C.sub.1 -C.sub.4 alkyl; or ##STR7## each R.sup.9 is independently H; C.sub.1 -C.sub.3 alkyl; halogen; hydroxy; C.sub.1 -C.sub.6 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; PA1 each R.sup.10 is independently H; C.sub.1 -C.sub.3 alkyl; hydroxy; or halogen; PA1 R.sup.11 and R.sup.12 are each independently H; halogen; C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.13 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.3 -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 ; PA1 R.sup.14 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkyl; CF.sub.3 ; or N(CH.sub.3).sub.2 ; PA1 W is N or CR.sup.15 ; PA1 R.sup.15 is H; C.sub.1 -C.sub.6 alkyl; halogen; or phenyl optionally substituted with C.sub.1 -C.sub.6 alkyl, 1-2 halogen, C.sub.1 -C.sub.6 alkoxy, or CF.sub.3 ; PA1 each Q is independently O or S; PA1 Q.sup.1 is O or S; PA1 Z.sup.1 is CR.sup.16 R.sup.17 ; O; S; S(O); S(O).sub.2 ; N(C.sub.1 -C.sub.4 alkyl; or ##STR8## each R.sup.16 is independently H; halogen; hydroxy; C.sub.1 -C.sub.6 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; PA1 each R.sup.17 is independently H; hydroxy; or halogen; or PA1 when R.sup.16 and R.sup.17 are bonded to adjacent atoms they can be taken together with the carbons to which they are attached to form ##STR9## R.sup.18 is C.sub.1 -C.sub.6 alkyl; halogen; or C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.19 and R.sup.20 are each independently H; C.sub.1 -C.sub.6 alkyl; or C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.21 and R.sup.22 are each independently C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 haloalkenyl; C.sub.3 -C.sub.6 alkynyl; or C.sub.3 -C.sub.6 haloalkynyl; PA1 R.sup.23 is halogen or cyano; PA1 R.sup.24 is C.sub.1 -C.sub.6 alkylsulfonyl; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkoxy; C.sub.1 -C.sub.6 haloalkoxy; or halogen; PA1 R.sup.25 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; and PA1 R.sup.26 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; or phenyl optionally substituted with C.sub.1 -C.sub.6 alkyl, 1-2 halogen, 1-2 nitro, C.sub.1 -C.sub.6 alkoxy, or CF.sub.3 ; PA1 provided that when X is O or S in Formula II, then J is other than J-6 or J-7. PA1 X is a direct bond or O; PA1 R.sup.1 is F or Cl; PA1 R.sup.2 is F; Cl; or Br; PA1 R.sup.3 is H; C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkoxyalkyl; C.sub.3 -C.sub.6 haloalkenyl; C.sub.1 -C.sub.6 alkylsufonyl; C.sub.3 -C.sub.6 alkoxycarbonylalkyl; C(O)R.sup.6 ; or benzyl optionally substituted on the phenyl ring with R.sup.7 ; PA1 R.sup.4 is H or halogen; PA1 R.sup.5 is H; PA1 J is J-1; J-2; J-3; J-4; J-5; J-6; J-8; J-12; J-15; or J-16; PA1 Z is CR.sup.9 R.sup.10 ; O; S; or N(C.sub.1 -C.sub.4 alkyl); PA1 each R.sup.9 is independently H; halogen; or C.sub.1 -C.sub.6 haloalkoxy; PA1 each R.sup.10 is independently H or halogen; PA1 each Q is O; PA1 Q.sup.1 is S; PA1 Z.sup.1 is CR.sup.16 R.sup.17 ; O; S; or N(C.sub.1 -C.sub.4 alkyl); PA1 each R.sup.16 is independently H; halogen; or haloalkoxy; PA1 each R.sup.17 is independently H or halogen; or PA1 when R.sup.16 and R.sup.17 are bonded to adjacent atoms they can be taken together with the carbons to which they are attached to form ##STR10## R.sup.18 is t-butyl or CH.sub.2 CH.sub.2 CH.sub.2 F; R.sup.23 is Cl or cyano; and PA1 R.sup.24 is C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.6 haloalkoxy. PA1 R.sup.2 is F or Cl; PA1 R.sup.3 is C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.6 alkoxycarbonylalkyl; or benzyl optionally substituted on the phenyl ring with R.sup.7 ; PA1 J is J-1; J-2; J-3; J-4; J-5; J-6; J-8; or J-12; PA1 Z is CR.sup.9 R.sup.10 or O; PA1 each R.sup.9 is independently H or halogen; PA1 R.sup.11 is C.sub.1 -C.sub.4 haloalkyl; PA1 R.sup.12 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.13 is CH.sub.3 ; PA1 R.sup.14 is CF.sub.3 ; PA1 W is CH; PA1 Z.sup.1 is CR.sup.16 R.sup.17 or O; PA1 each R.sup.16 is independently H or halogen; PA1 each R.sup.17 is independently H or halogen; or PA1 when R.sup.16 and R.sup.17 are bonded to adjacent atoms they can be taken together with the carbons to which they are attached to form ##STR11## Preferred 3. Compounds of Preferred 2 wherein: R.sup.2 is Cl; PA1 R.sup.3 is C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; PA1 J is J-1; J-2; J-3; J-4; J-6; or J-12; PA1 Z is CR.sup.9 R.sup.10 ; PA1 R.sup.9 is independently H or F; PA1 R.sup.10 is independently H or F; PA1 R.sup.11 is CF.sub.2 H; PA1 R.sup.12 is CH.sub.3 ; PA1 Z.sup.1 is CR.sup.16 R.sup.17 ; PA1 R.sup.16 is independently H or F; and PA1 R.sup.17 is independently H or F.
The cyclic sulfonamides of the present invention are not disclosed in either of these references.
USPTO Backgrounds
USPTO Backgrounds