Herbicidal bicyclic and tricyclic imides

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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504221, 504225, 504261, 504280, 504285, 504286, 544 82, 544105, 544236, 5482624, 548453, 548454, 548513, C07D48702, A01N 4356

Patent

active

057191042

DESCRIPTION:

BRIEF SUMMARY
This invention comprises certain bicyclic imides, their agriculturally-suitable salts and compositions, and methods of their use for weed control in crops.
WO 909575 (BASF) discloses compounds of formula i ##STR2## wherein R.sub.1 =halogen, R.sub.2 =alkyl, etc., R.sub.3 =H or CH.sub.3, X =H or halogen, and Y=halogen. The compounds of the present invention differ from those disclosed in this reference in that a non-hydrogen, non-alkyl substituent is present on the cyclohexene ring moiety.
JP 3,063,278 (Nissan) discloses compounds of Formula ii ##STR3## wherein Z is O or S, and R.sub.1 is H, alkyl, haloalkyl, etc. The N-phenyl tetrahydrotriazolopyridazines of the present invention differ from the compounds disclosed in JP 3,063,278 in the nature of the substitution on the tetrahydropyridazine ring.
U.S. Pat. Nos. 4,881,967, 5,077,401, and 5,108,483 also disclose related tetrahydrotriazolopyridazines. The compounds of the present invention also differ from the compounds disclosed in these references in the nature of the substitution on the tetrahydropyridazine ring.


SUMMARY OF THE INVENTION

This invention pertains to compounds of Formulae I and II, or an agriculturally-suitable salt thereof, for controlling undesirable vegetation: ##STR4## wherein G is O; S; NH; N(C.sub.1 -C.sub.4 alkyl); or N(C.sub.1 -C.sub.4 haloalkyl); -C.sub.3 haloalkoxy; C.sub.1 -C.sub.3 alkylthio; C.sub.1 -C.sub.3 haloalkylthio; C.sub.2 -C.sub.4 alkylcarbonyloxy; or C.sub.2 -C.sub.4 haloalkylcarbonyloxy; taken together with the carbon to which they are attached to form C.dbd.O; or together with the carbons to which they are attached to form ##STR5## Y and Z are each independently H; halogen; C.sub.1 -C.sub.2 alkyl; or C.sub.1 -C.sub.2 haloalkyl; CHOCH.sub.2 CF.sub.3 ; O; S(O).sub.0-2 ; NH; N(C.sub.1 -C.sub.4 alkyl); or N(C.sub.1 -C.sub.4 haloalkyl); ##STR6## W is O or S; R.sup.3 is chlorine or fluorine; OH; OR.sup.9 ; SH; S(O).sub.p R.sup.9 ; COR.sup.9 ; CO.sub.2 R.sup.9 ; C(O)SR.sup.9 ; C(O)NR.sup.11 R.sup.12 ; CHO; CR.sup.11 =NOR.sup.18 ; CH.dbd.CR.sup.19 CO.sub.2 R.sup.9 ; CH.sub.2 CHR.sup.19 CO.sub.2 R.sup.9 ; CO.sub.2 N.dbd.CR.sup.13 R.sup.14 ; NO.sub.2 ; CN; NHSO.sub.2 R.sup.15 ; NHSO.sub.2 NHR.sup.15 ; NR.sup.9 R.sup.20 ; NH.sub.2 or phenyl optionally substituted with at least one member independently selected from C.sub.1 -C.sub.4 alkyl; SCH.sub.3 ; OCHF.sub.2 ; halogen; CN or NO.sub.2 ; halogen; cyclopropyl; vinyl; C.sub.2 alkynyl; CN; C(O)R.sub.20 ; CO.sub.20 R.sup.20 ; C(O)NR.sup.20 R.sup.21 ; CR.sup.16 R.sup.17 CN; CR.sup.16 R.sup.17 C(O)R.sup.20 ; CR.sup.16 R.sup.17 CO.sub.2 R.sup.20 ; CR.sup.16 R.sup.17 C(O)NR.sup.20 R.sup.21 ; CHR.sup.16 OH; CHR.sup.16 OC(O)R.sup.20 ; OCHR.sup.16 OC(O)NR.sup.20 R.sup.21 ; or Q is Q-2 and R.sup.6 and R.sup.7 are taken together with the carbon to which they are attached to form C.dbd.O; -C.sub.6 alkoxyalkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; -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.2 -C.sub.8 alkylthioalkyl; C.sub.2 -C.sub.8 alkylsulfmylalkyl; C.sub.2 -C.sub.8 alkylsulfonylalkyl; C.sub.1 -C.sub.8 alkylsulfonyl; phenylsulfonyl optionally substituted on the phenyl ring with at least one substituent selected from the group halogen and C.sub.1 -C.sub.4 alkyl; C.sub.4 -C.sub.8 alkoxyalkoxyalkyl; C.sub.4 -C.sub.8 cycloalkylalkyl; C.sub.4 -C.sub.8 alkenoxyalkyl; C.sub.4 -C.sub.8 alkynoxyalkyl; C.sub.6 -C.sub.8 cycloalkoxyalkyl; C.sub.4 -C.sub.8 alkenyloxyalkyl; C.sub.4 -C.sub.8 alkynyloxyalkyl; C.sub.3 -C.sub.8 haloalkoxyalkyl; C.sub.4 -C.sub.8 haloalkenoxyalkyl; C.sub.4 -C.sub.8 haloalkynoxyalkyl; C.sub.6 -C.sub.8 cycloalkylthioalkyl; C.sub.4 -C.sub.8 alkenylthioalkyl; C.sub.4 -C.sub.8 alkynylthioalkyl; C.sub.1 -C.sub.4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with at least one substituent selected from the group halogen, C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl; C.sub.4 -C.sub.8 trialkylsilylalkyl; C.sub.3 -C.sub.8 cyanoakyl; C.sub.3 -C.sub.8 halocycloalkyl

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