HERBICIDAL CYCLIC AMIDES N-SUBSTITUTED WITH A HALOALKYLSULFONYLANILIDE GROUP
20240158348 ยท 2024-05-16
Inventors
Cpc classification
C07D405/12
CHEMISTRY; METALLURGY
A01N25/32
HUMAN NECESSITIES
C07D207/273
CHEMISTRY; METALLURGY
A01N47/02
HUMAN NECESSITIES
A01N43/84
HUMAN NECESSITIES
International classification
A01N25/32
HUMAN NECESSITIES
A01N47/02
HUMAN NECESSITIES
Abstract
Disclosed are compounds of Formula 1, all stereoisomers, N-oxides, and salts thereof,
##STR00001##
wherein R.sup.1 through R.sup.8, R.sup.f, Q and G are as defined in the Disclosure.
Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.
Claims
1. A compound selected from Formula 1, all stereoisomers, N-oxides, and salts thereof, ##STR00073## wherein R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 haloalkynyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl or C.sub.2-C.sub.7 haloalkoxyalkyl; R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 haloalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.5 alkylthio; R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 haloalkynyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl or C.sub.2-C.sub.7 haloalkoxyalkyl; R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; or propargyl, allyl or benzyl; R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 haloalkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 haloalkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; Q is CHR.sup.9, O or a direct bond; R.sup.9 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; or G and R.sup.5 are taken together to form NOR.sup.15; R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.1-C.sub.6 nitroalkyl, C.sub.3-C.sub.6 alkylcarboalkyl, C.sub.3-C.sub.6 alkoxycarboalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.3-C.sub.6 alkylcarboalkoxy; or R.sup.10 is selected from the group consisting of ##STR00074## ##STR00075## R.sup.11 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.12 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.7 haloalkyl; each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.3 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkylalkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy; C.sub.2-C.sub.7 alkoxyalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, Ph or benzyl; R.sup.f is C.sub.1-C.sub.7 haloalkyl; G and R.sup.8 can be attached to any ring carbon(s) with available valency, said ring is the cyclic amide ring shown in Formula 1; each R.sup.11 or R.sup.12 can be attached to any ring carbon(s) with available valency, said ring is illustrated in R.sup.10-1 through R.sup.10-16 as above; and R.sup.15 is H, 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 alkynyl or C.sub.4-C.sub.7 cycloalkylalkyl.
2. The compound of claim 1 wherein Q is direct bond; R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.11 is H or C.sub.1-C.sub.7 alkyl; R.sup.12 is H or C.sub.1-C.sub.7 alkyl; each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and R.sup.f is C.sub.1-C.sub.3 haloalkyl.
3. The compound of claim 2 wherein R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; R.sup.2 is H, Me, F, Cl or CN; R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; G is OR.sup.10 or SR.sup.10; and R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl.
4. The compound of claim 3 wherein R.sup.1 is H, Me, halogen or cyclopropyl; R.sup.2 is H or F; R.sup.3 is Me or F; R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; R.sup.5 is H; R.sup.6 is H, Me or OMe; R.sup.7 is H, Me or OMe; R.sup.8 is H, Me or OMe; G is OR.sup.10; R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl or C.sub.4-C.sub.7 alkylcycloalkyl.
5. (canceled)
6. (canceled)
7. The compound of claim 1 wherein Q is CHR.sup.9; R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; R.sup.9 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.11 is H or C.sub.1-C.sub.7 alkyl; R.sup.12 is H or C.sub.1-C.sub.7 alkyl; each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and R.sup.f is C.sub.1-C.sub.3 haloalkyl.
8. The compound of claim 7 wherein R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; R.sup.2 is H, Me, F, Cl or CN; R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; G is OR.sup.10 or SR.sup.10; R.sup.9 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; and R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl or C.sub.4-C.sub.7 alkylcycloalkyl;
9. (canceled)
10. (canceled)
11. The compound of claim 1 wherein Q is O; R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl; R.sup.11 is H or C.sub.1-C.sub.7 alkyl; R.sup.12 is H or C.sub.1-C.sub.7 alkyl; each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and R.sup.f is C.sub.1-C.sub.3 haloalkyl.
12. The compound of claim 11 wherein R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; R.sup.2 is H, Me, F, Cl or CN; R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; G is OR.sup.10 or SR.sup.10; and R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl.
13. The compound of claim 12 wherein R.sup.1 is H, Me, halogen or cyclopropyl; R.sup.2 is H or F; R.sup.3 is Me or F; R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; R.sup.5 is H; R.sup.6 is H, Me or OMe; R.sup.7 is H, Me or OMe; R.sup.8 is H, Me or OMe; G is OR.sup.10; R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl or C.sub.4-C.sub.7 alkylcycloalkyl.
14. (canceled)
15. (canceled)
16. The compound of claim 1 wherein R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; G and R.sup.5 are taken together to form NOR.sup.15; R.sup.11 is H or C.sub.1-C.sub.7 alkyl; R.sup.12 is H or C.sub.1-C.sub.7 alkyl; each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; R.sup.f is C.sub.1-C.sub.3 haloalkyl; and R.sup.15 is H, 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 alkynyl or C.sub.4-C.sub.7 cycloalkylalkyl.
17. The compound of claim 16 wherein R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; R.sup.2 is H, Me, F, Cl or CN; R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; and R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy.
18. The compound of claim 17 wherein R.sup.1 is H, Me, halogen or cyclopropyl; R.sup.2 is H or F; R.sup.3 is Me or F; R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; R.sup.6 is H, Me or OMe; R.sup.7 is H, Me or OMe; and R.sup.8 is H, Me or OMe.
19. The compound of claim 18 wherein R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; and R.sup.8 is H.
20. (canceled)
21. The compound of claim 16 wherein Q is direct bond.
22. The compound of claim 1 selected from the group consisting of TABLE-US-00054 N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 6); [[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 5) N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1- trifluoromethanesulfonamide (Compound 1); N-[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 3); [[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 7); [[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 8); N-[2,4-dimethyl-5-[2-oxo-3-(2-propen-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1- trifluoromethanesulfonamide (Compound 2); and N-[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 4).
23. The compound of claim 1 selected from the group consisting of TABLE-US-00055 N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 6); [[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 5) N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1- trifluoromethanesulfonamide (Compound 1); N-[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 3); [5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 7); [[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 8); N-[2,4-dimethyl-5-[2-oxo-3-(2-propen-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1- trifluoromethanesulfonamide (Compound 2); and N-[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 4). N-[5-[3-(Ethoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 12) N-[2,4-Dimethyl-5-[2-oxo-3-[(2-propyn-1-yloxy)imino]-1-pyrrolidinyl]phenyl]-1,1,1- trifluoromethanesulfonamide (Compound 13) 1,1,1-Trifluoro-N-[5-[3-(methoxyimino)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl]methanesulfonamide (Compound 9)
24. A herbicidal composition comprising a compound of claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
25. A herbicidal composition comprising a compound of claim 1, at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
26. A herbicidal mixture comprising (a) a compound of claim 1, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solanesyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts of compounds of (b1) through (b16).
27. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1.
28. The method of claim 29 further comprising contacting the vegetation or its environment with a herbicidally effective amount of at least one additional active ingredient selected from (b1) through (b16) and salts of compounds of (b1) through (b16).
29. The compound of claim 17 wherein Q is direct bond.
30. The compound of claim 18 wherein Q is direct bond.
31. The compound of claim 19 wherein Q is direct bond.
Description
DETAILS OF THE INVENTION
[0026] As used herein, the terms comprises, comprising, includes, including, has, having, contains, containing, characterized by or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process, method, article or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, method, article or apparatus.
[0027] The transitional phrase consisting of excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
[0028] The transitional phrase consisting essentially of is used to define a composition, method or apparatus that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term consisting essentially of occupies a middle ground between comprising and consisting of.
[0029] Where applicants have defined an invention or a portion thereof with an open-ended term such as comprising, it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms consisting essentially of or consisting of
[0030] Further, unless expressly stated to the contrary, or refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
[0031] Also, the indefinite articles a and an preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore a or an should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
[0032] As referred to herein, the term seedling, used either alone or in a combination of words means a young plant developing from the embryo of a seed.
[0033] As referred to herein, the term broadleaf used either alone or in words such as broadleaf weed means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
[0034] In the above recitations, the term alkyl, used either alone or in compound words such as alkylthio or haloalkyl includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl or the different butyl, pentyl or hexyl isomers. Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. Alkenylalkyl denotes alkenyl substitution on alkyl. Examples of alkenylalkyl include CH.sub.2?CHCH.sub.2, CH.sub.3CH?CHCH.sub.2, CH.sub.2?CHCH.sub.2CH.sub.2, CH.sub.2?CHCH(CH.sub.3)CH.sub.2 and the different alkenylalkyl isomers. Alkenylalkyl is a subset of alkenyl. Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl, CH?CCH.sub.2CH.sub.2, CH.sub.3C==CCH.sub.2 and the different butynyl, pentynyl and hexynyl isomers. Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. Alkynylalkyl denotes alkynyl substitution on alkyl. Examples of alkynylalkyl include CH?CCH.sub.2, CH.sub.3C==CCH.sub.2, CH?CCH.sub.2CH.sub.2, CH?CCH(CH.sub.3)CH.sub.2 and the different alkynylalkyl isomers. Alkynylalkyl is a subset of alkynyl. Alkylene denotes a straight-chain or branched alkanediyl. Examples of alkylene include CH.sub.2, CH.sub.2CH.sub.2, CH(CH.sub.3), CH.sub.2CH.sub.2CH.sub.2, CH.sub.2CH(CH.sub.3) and the different butylene isomers. Alkenylene denotes a straight-chain or branched alkenediyl containing one olefinic bond. Examples of alkenylene include CH?CH, CH.sub.2CH?CH, CH?C(CH.sub.3) and the different butenylene isomers. Alkynylene denotes a straight-chain or branched alkynediyl containing one triple bond. Examples of alkynylene include C?C, CH.sub.2C?C, C?CCH.sub.2 and the different butynylene isomers.
[0035] Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of alkoxyalkyl include CH.sub.3OCH.sub.2, CH.sub.3OCH.sub.2CH.sub.2, CH.sub.3CH.sub.2OCH.sub.2, CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2 and CH.sub.3CH.sub.2OCH.sub.2CH.sub.2. Alkoxyalkoxy denotes alkoxy substitution on alkoxy. Alkenyloxy includes straight-chain or branched alkenyloxy moieties. Examples of alkenyloxy include H.sub.2C?CHCH.sub.2O, (CH.sub.3).sub.2C?CHCH.sub.2O, (CH.sub.3)CH?CHCH.sub.2O, (CH.sub.3)CH?C(CH.sub.3)CH.sub.2O and CH.sub.2?CHCH.sub.2CH.sub.2O. Alkynyloxy includes straight-chain or branched alkynyloxy moieties. Examples of alkynyloxy include HC?CCH.sub.2O, CH.sub.3C?CCH.sub.2O and CH.sub.3C?CCH.sub.2CH.sub.2O. Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group. Examples of alkylsulfinyl include CH.sub.3S(O), CH.sub.3CH.sub.2S(O), CH.sub.3CH.sub.2CH.sub.2S(O), (CH.sub.3).sub.2CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of alkylsulfonyl include CH.sub.3S(O).sub.2, CH.sub.3CH.sub.2S(O).sub.2, CH.sub.3CH.sub.2CH.sub.2S(O).sub.2, (CH.sub.3).sub.2CHS(O).sub.2, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. Alkylthioalkyl denotes alkylthio substitution on alkyl. Examples of alkylthioalkyl include CH.sub.3SCH.sub.2, CH.sub.3SCH.sub.2CH.sub.2, CH.sub.3CH.sub.2SCH.sub.2, CH.sub.3CH.sub.2CH.sub.2CH.sub.2SCH.sub.2 and CH.sub.3CH.sub.2SCH.sub.2CH.sub.2. Alkylthioalkoxy denotes alkylthio substitution on alkoxy. Alkyldithio denotes branched or straight-chain alkyldithio moieties. Examples of alkyldithio include CH.sub.3SS, CH.sub.3CH.sub.2SS, CH.sub.3CH.sub.2CH.sub.2SS, (CH.sub.3).sub.2CHSS and the different butyldithio and pentyldithio isomers. Cyanoalkyl denotes an alkyl group substituted with one cyano group. Examples of cyanoalkyl include NCCH.sub.2, NCCH.sub.2CH.sub.2 and CH.sub.3CH(CN)CH.sub.2. Alkylamino, dialkylamino, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkynylthio, alkynylsulfinyl, alkynylsulfonyl, and the like, are defined analogously to the above examples.
[0036] Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term alkylcycloalkyl denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term cycloalkylalkyl denotes cycloalkyl substitution on an alkyl moiety. Examples of cycloalkylalkyl include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. Examples of alkylcycloalkylalkyl include 2-methylcyclopropylmethyl, methylcyclopentylethyl, and other alkylcycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term cycloalkoxy denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. Cycloalkylalkoxy denotes cycloalkylalkyl linked through an oxygen atom attached to the alkyl chain. Examples of cycloalkylalkoxy include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. Cyanocycloalkyl denotes a cycloalkyl group substituted with one cyano group. Examples of cyanocycloalkyl include 4-cyanocyclohexyl and 3-cyanocyclopentyl. Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl.
[0037] The term halogen, either alone or in compound words such as haloalkyl or when used in descriptions such as alkyl substituted with halogen includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as haloalkyl or when used in descriptions such as alkyl substituted with halogen said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of haloalkyl or alkyl substituted with halogen include F.sub.3C, ClCH.sub.2, CF.sub.3CH.sub.2 and CF.sub.3CCl.sub.2. The terms halocycloalkyl, haloalkoxy, haloalkylthio, haloalkenyl, haloalkynyl, and the like, are defined analogously to the term haloalkyl. Examples of haloalkoxy include CF.sub.3O, CCl.sub.3CH.sub.2O, HCF.sub.2CH.sub.2CH.sub.2O and CF.sub.3CH.sub.2O. Examples of haloalkylthio include CCl.sub.3S, CF.sub.3S, CCl.sub.3CH.sub.2S and ClCH.sub.2CH.sub.2CH.sub.2S. Examples of haloalkylsulfinyl include CF.sub.3S(O), CCl.sub.3S(O), CF.sub.3CH.sub.2S(O) and CF.sub.3CF.sub.2S(O). Examples of haloalkylsulfonyl include CF.sub.3S(O).sub.2, CCl.sub.3S(O).sub.2, CF.sub.3CH.sub.2S(O).sub.2 and CF.sub.3CF.sub.2S(O).sub.2. Examples of haloalkenyl include (C.sub.1).sub.2C?CHCH.sub.2 and CF.sub.3CH.sub.2CH?CHCH.sub.2. Examples of haloalkynyl include HC?CCHCl, CF.sub.3C?C, CCl.sub.3C?C and FCH.sub.2C?CCH.sub.2. Examples of haloalkoxyalkoxy include CF.sub.3OCH.sub.2O, C.sub.1CH.sub.2CH.sub.2OCH.sub.2CH.sub.2O, Cl.sub.3CCH.sub.2OCH.sub.2O as well as branched alkyl derivatives. Examples of haloalkoxyalkyl include CF.sub.3OCH.sub.2, ClCH.sub.2CH.sub.2OCH.sub.2CH.sub.2, Cl.sub.3CCH.sub.2OCH.sub.2CH.sub.2 as well as branched alkyl derivatives.
[0038] Alkylcarbonyl denotes a straight-chain or branched alkyl moieties bonded to a C(?O) moiety. Examples of alkylcarbonyl include CH.sub.3C(?O), CH.sub.3CH.sub.2CH.sub.2C(?O) and (CH.sub.3).sub.2CHC(?O). Alkylcarboalkoxy denotes a straight-chain or branched alkoxy substituted with alkylcarbonyl group. Examples of Alkylcarboalkoxy include CH.sub.3C(?O) CH.sub.2O, CH.sub.3CH.sub.2CH.sub.2C(?O)CH.sub.2O and (CH.sub.3).sub.2CHC(?O)CH.sub.2CH.sub.2O. Examples of alkoxycarbonyl include CH.sub.3OC(?O), CH.sub.3CH.sub.2OC(?O), CH.sub.3CH.sub.2CH.sub.2OC(?O), (CH.sub.3).sub.2CHOC(?O) and the different butoxy- or pentoxycarbonyl isomers.
[0039] Alkoxycarboalkyl denotes a straight-chain or branched alkyl substituted with alkoxycarbonyl group. Examples of alkoxycarboalkyl include CH.sub.3OC(?O)CH.sub.2, CH.sub.3CH.sub.2OC(?O)CH.sub.2CH.sub.2, CH.sub.3CH.sub.2CH.sub.2OC(?O)CH.sub.2, (CH.sub.3).sub.2CHOC(?O)CH(CH.sub.3)CH.sub.2 and the different butoxy- or pentoxycarbonylalkyl isomers.
[0040] The total number of carbon atoms in a substituent group is indicated by the C.sub.i-C.sub.j prefix where i and j are numbers from 1 to 7. In other words, i and j indicate the total number of carbon atoms in this group, and i through j indicates the range of the possible total number of the carbon atoms in the group. For example, C.sub.1-C.sub.4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C.sub.2-C.sub.6 alkenyl designates ethenyl through hexenyl, and the different propenyl, butenyl, pentenyl and hexenyl isomers. C.sub.2 alkoxyalkyl designates CH.sub.3OCH.sub.2; C.sub.3 alkoxyalkyl designates, for example, CH.sub.3CH(OCH.sub.3), CH.sub.3OCH.sub.2CH.sub.2 or CH.sub.3CH.sub.2OCH.sub.2; and C.sub.4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH.sub.3CH.sub.2CH.sub.2OCH.sub.2 and CH.sub.3CH.sub.2OCH.sub.2CH.sub.2.
[0041] When a group contains a substituent which can be hydrogen, for example R.sup.2, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted at this position. When one or more positions on a group are said to be not substituted or unsubstituted, then hydrogen atoms are attached to take up any free valency.
[0042] For substituents G, R.sup.8, R.sup.11 or R.sup.12, the attachment point of these substituents is illustrated as floating, which means each of these substituents can be attached to any of the available carbons on the ring, to which they are attached, by replacement of a hydrogen atom. For example, G or R.sup.8 can be attached to any ring carbon(s) with available valency by replacement of a hydrogen atom, said ring is the cyclic amide ring as shown in Formula 1. For example, when Q is CHR.sup.9, G can be attached to the said carbon by replacement of the H of CHR.sup.9 to form a moiety of C(G)R.sup.9. R.sup.11 or R.sup.12 can be attached to any ring carbon(s) with available valency by replacement of a hydrogen atom, said ring is illustrated in R.sup.10-1 through R.sup.10-16 in the Summary of The Disclosure. In this disclosure, the cyclic amide ring always has the substituent G.
[0043] Unless otherwise indicated, a ring as a component of Formula 1 is carbocyclic or heterocyclic. For example, a cyclic amide ring is a ring containing a NCO group, it can optionally contain more heteroatom(s) as the ring member(s). The term ring member refers to an atom or other moiety (e.g., C(?O), C(?S), S(O) or S(O).sub.2) forming the backbone of a ring or ring system.
[0044] Some non-limiting examples of cyclic amide rings in this disclosure are illustrated in Exhibit 1 wherein each structure is associated with a L-# and the # is a number. When the substituent on the cyclic amide ring is G, but not specified for other substituents on the same carbon to which G is bonded (e.g., L-2, L-4, L-6, L-8, L-10, L-12, L-14, L-16 and L-18) then H or R.sup.8 can take up the remaining valance on said carbon. G and R.sup.5 can also be taken together to form NOR.sup.15, wherein the N is attached to the carbon ring member through a double bond to form an oxime moiety, such as in L-19.
Exhibit 1
[0045] ##STR00004## ##STR00005## ##STR00006##
[0046] In one specific embodiment, G and R.sup.5 can be taken together to form NOR.sup.15, wherein the N is attached to the carbon ring member through a double bond to form an oxime moirty, as shown below.
##STR00007##
[0047] The terms heterocyclic ring, heterocycle or heterocyclic ring system denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically, a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies H?ckel's rule, then said ring is also called a heteroaromatic ring or aromatic heterocyclic ring. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
[0048] Aromatic indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and that (4n+2) ? electrons, where n is a positive integer, are associated with the ring to comply with H?ckel's rule. The term aromatic ring system denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. The term aromatic carbocyclic ring system denotes a carbocyclic ring system in which at least one ring of the ring system is aromatic. The term aromatic heterocyclic ring system denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term nonaromatic ring system denotes a carbocyclic or heterocyclic ring system that may be fully saturated, as well as partially or fully unsaturated, provided that none of the rings in the ring system are aromatic. The term nonaromatic carbocyclic ring system in which no ring in the ring system is aromatic. The term nonaromatic heterocyclic ring system denotes a heterocyclic ring system in which no ring in the ring system is aromatic.
[0049] The term optionally substituted is used interchangeably with the phrase substituted or unsubstituted or with the term (un)substituted. Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.
[0050] In Formula 1, when G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10, R.sup.10 can be (among others) J. Some non-limiting examples of J are illustrated in the table of Exhibit 2 wherein each structure is associated with a J-# and the # is a number.
Exhibit 2
[0051] ##STR00008## ##STR00009##
[0052] A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.
[0053] Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers) and atropisomers. Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
[0054] For example, when G and R.sup.5 are different and attached to the same carbon, the compound of Formula 1 may have at least two stereoisomers. The two stereoisomers are depicted as Formula 1 and Formula 1 with the chiral center identified with an asterisk (*). For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.
##STR00010##
[0055] Molecular depictions drawn herein follow standard conventions for depicting stereochemistry. To indicate stereoconfiguration, bonds rising from the plane of the drawing and towards the viewer are denoted by solid wedges wherein the broad end of the wedge is attached to the atom rising from the plane of the drawing towards the viewer. Bonds going below the plane of the drawing and away from the viewer are denoted by dashed wedges wherein the broad end of the wedge is attached to the atom further away from the viewer. Constant width lines indicate bonds with a direction opposite or neutral relative to bonds shown with solid or dashed wedges; constant width lines also depict bonds in molecules or parts of molecules in which no particular stereoconfiguration is intended to be specified.
[0056] This invention comprises racemic mixtures, for example, equal amounts of the enantiomers of Formulae 1 and 1. In addition, this invention includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula 1. Also included are the essentially pure enantiomers of compounds of Formula 1, for example, Formula 1 or Formula 1.
[0057] When enantiomerically enriched, one enantiomer is present in greater amounts than the other, and the extent of enrichment can be defined by an expression of enantiomeric excess (ee), which is defined as (2x?1) 100%, where x is the mole fraction of the dominant enantiomer in the mixture (e.g., an ee of 20% corresponds to a 60:40 ratio of enantiomers).
[0058] Preferably the compositions of this invention have at least a 50% enantiomeric excess; more preferably at least a 75% enantiomeric excess; still more preferably at least a 90% enantiomeric excess; and the most preferably at least a 94% enantiomeric excess of the more active isomer. Of particular note are enantiomerically pure embodiments of the more active isomer.
[0059] Compounds of Formula 1 may comprise additional chiral centers. For example, substituents and other molecular constituents, such as G and R.sup.5, may themselves contain chiral centers. This invention comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers.
[0060] Compounds of this invention can exist as one or more conformational isomers due to any restricted bond rotation in Formula 1. This invention comprises mixtures of conformational isomers. In addition, this invention includes compounds that are enriched in one conformer relative to others.
[0061] Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.
[0062] One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
[0063] One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus, a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
[0064] Embodiments of the present invention as described in the Summary of the Disclosure include those wherein a compound of Formula 1 is as described in any of the following Embodiments: [0065] Embodiment 1. A compound of Formula 1, as described in the Summary of the Disclosure, all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Disclosure. [0066] Embodiment 2. A compound of Formula 1 or Embodiment 1 wherein Q is CHR.sup.9, O or a direct bond. [0067] Embodiment 2a. A compound of Formula 1 or Embodiment 2 wherein Q is CHR.sup.9 or a direct bond. [0068] Embodiment 2b. A compound of Formula 1 or Embodiment 2a wherein Q is CHR.sup.9. [0069] Embodiment 2c. A compound of Formula 1 or Embodiment 2a wherein Q is direct bond. [0070] Embodiment 2d. A compound of Formula 1 or Embodiment 2 wherein Q is O. [0071] Embodiment 3. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl. [0072] Embodiment 3a. A compound of Embodiment 3 wherein R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.3-C.sub.7 cycloalkyl. [0073] Embodiment 3b. A compound of Embodiment 3a wherein R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl. [0074] Embodiment 3c. A compound of Embodiment 3b wherein R.sup.1 is H, Me, halogen or cyclopropyl. [0075] Embodiment 3d. A compound of Embodiment 3c wherein R.sup.1 is H, Me, F, Cl, Br or cyclopropyl. [0076] Embodiment 3e. A compound of Embodiment 3d wherein R.sup.1 is Me or C.sub.1. [0077] Embodiment 3f A compound of Embodiment 3e wherein R.sup.1 is Me. [0078] Embodiment 3g. A compound of Embodiment 3e wherein R.sup.1 is C.sub.1. [0079] Embodiment 3h. A compound of Embodiment 3d wherein R.sup.1 is H. [0080] Embodiment 4. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 haloalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.5 alkylthio. [0081] Embodiment 4a. A compound of Embodiment 4 wherein R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN. [0082] Embodiment 4b. A compound of Embodiment 4a wherein R.sup.2 is H, Me, F, Cl or CN. [0083] Embodiment 4c. A compound of Embodiment 4b wherein R.sup.2 is H or F. [0084] Embodiment 4d. A compound of Embodiment 4c wherein R.sup.2 is H. [0085] Embodiment 4e. A compound of Embodiment 4c wherein R.sup.2 is F. [0086] Embodiment 5. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 haloalkynyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl or C.sub.2-C.sub.7 haloalkoxyalkyl. [0087] Embodiment 5a. A compound of Embodiment 5 wherein R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl. [0088] Embodiment 5b. A compound of Embodiment 5a wherein R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3. [0089] Embodiment 5c. A compound of Embodiment 5b wherein R.sup.3 is Me or F. [0090] Embodiment 5d. A compound of Embodiment 5c wherein R.sup.3 is Me. [0091] Embodiment 6. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, C(?O)OR.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; or propargyl, allyl or benzyl. [0092] Embodiment 6a. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, C(?O)OR.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14. [0093] Embodiment 6aa. A compound of Embodiment 6 wherein R.sup.4 is H, C(?O)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, CH.sub.2OC(?O)OR.sup.14 or CH.sub.2OCOR.sup.14. [0094] Embodiment 6b. A compound of Embodiment 6aa wherein R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr, CH.sub.2OCO-i-Pr or (C?O)SMe. [0095] Embodiment 6c. A compound of Embodiment 6a wherein R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14. [0096] Embodiment 6d. A compound of Embodiment 6c wherein R.sup.4 is H, CH.sub.2OCO-t-Bu or S(O).sub.2CF.sub.3. [0097] Embodiment 6e. A compound of Embodiment 6d wherein R.sup.4 is H. [0098] Embodiment 6f. A compound of Embodiment 6d wherein R.sup.4 is S(O).sub.2CF.sub.3. [0099] Embodiment 6g. A compound of Embodiment 6 wherein R.sup.4 is propargyl, allyl or benzyl. [0100] Embodiment 6h. A compound of Embodiment 6g wherein R.sup.4 is benzyl. [0101] Embodiment 6g. A compound of Embodiment 6 wherein R.sup.4 is propargyl. [0102] Embodiment 6g. A compound of Embodiment 6 wherein R.sup.4 is allyl. [0103] Embodiment 7. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0104] Embodiment 7a. A compound of Embodiment 7 wherein R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; Embodiment 7b. A compound of Embodiment 7a wherein R.sup.5 is H. [0105] Embodiment 8. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy or C.sub.4-C.sub.7 alkylcycloalkyl. [0106] Embodiment 8a. A compound of Embodiment 8 wherein R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0107] Embodiment 8b. A compound of Embodiment 8a wherein R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0108] Embodiment 8c. A compound of Embodiment 8b wherein R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy. [0109] Embodiment 8d. A compound of Embodiment 8b wherein R.sup.6 is H, Me or OMe. [0110] Embodiment 8e. A compound of Embodiment 8d wherein R.sup.6 is H. [0111] Embodiment 8f. A compound of Embodiment 8d wherein R.sup.6 is Me. [0112] Embodiment 8g. A compound of Embodiment 8d wherein R.sup.6 is OMe. [0113] Embodiment 9. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy or C.sub.4-C.sub.7 alkylcycloalkyl. [0114] Embodiment 9a. A compound of Embodiment 9 wherein R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0115] Embodiment 9b. A compound of Embodiment 9a wherein R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0116] Embodiment 9c. A compound of Embodiment 9b wherein R.sup.7 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy. [0117] Embodiment 9d. A compound of Embodiment 9b wherein R.sup.7 is H, Me or OMe. [0118] Embodiment 9e. A compound of Embodiment 9d wherein R.sup.7 is H. [0119] Embodiment 9f. A compound of Embodiment 8d wherein R.sup.7 is Me. [0120] Embodiment 9g. A compound of Embodiment 9d wherein R.sup.7 is OMe. [0121] Embodiment 10. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0122] Embodiment 10a. A compound of Embodiment 10 wherein R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0123] Embodiment 10b. A compound of Embodiment 10a wherein R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0124] Embodiment 10c. A compound of Embodiment 10b wherein R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy. [0125] Embodiment 10d. A compound of Embodiment 10b wherein R.sup.8 is H, Me or OMe. [0126] Embodiment 10e. A compound of Embodiment 10d wherein R.sup.8 is H. [0127] Embodiment 10f A compound of Embodiment 10d wherein R.sup.8 is Me. [0128] Embodiment 10g. A compound of Embodiment 10d wherein R.sup.8 is OMe. [0129] Embodiment 11. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.9 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy or C.sub.4-C.sub.7 alkylcycloalkyl. [0130] Embodiment 11a. A compound of Embodiment 11 wherein R.sup.9 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0131] Embodiment 11b. A compound of Embodiment 11a wherein R.sup.9 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy. [0132] Embodiment 11c. A compound of Embodiment 11b wherein R.sup.9 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy. [0133] Embodiment 11d. A compound of Embodiment 11b wherein R.sup.9 is H, Me or OMe. [0134] Embodiment 11e. A compound of Embodiment 11d wherein R.sup.9 is H. [0135] Embodiment 1 if A compound of Embodiment 11d wherein R.sup.9 is Me. [0136] Embodiment 11g. A compound of Embodiment 11d wherein R.sup.9 is OMe. [0137] Embodiment 12. A compound of Formula 1 or any one of the preceding Embodiments wherein G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; or G and R.sup.5 are taken together to form NOR.sup.15 where R.sup.15 is H, 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 alkynyl or C.sub.4-C.sub.7 cycloalkylalkyl. [0138] Embodiment 12a. A compound of Embodiment 12 wherein G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10. [0139] Embodiment 12aa. A compound of Embodiment 12a wherein G is OR.sup.10 or SR.sup.10 [0140] Embodiment 12b. A compound of Embodiment 12aa wherein G is OR.sup.10. [0141] Embodiment 12c. A compound of Embodiment 12aa wherein G is SR.sup.10. [0142] Embodiment 12d. A compound of Embodiment 12 wherein G is SOR.sup.10. [0143] Embodiment 12e. A compound of Embodiment 12 wherein G is SO.sub.2R.sup.10. [0144] Embodiment 12f. A compound of Embodiment 12 wherein G and R.sup.5 are attached to the same carbon ring member. [0145] Embodiment 12g. A compound of Embodiment 12 wherein G and R.sup.5 are taken together to form NOR.sup.15. [0146] Embodiment 12gg. A compound of Embodiment 12g wherein R.sup.15 is H, 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 alkynyl or C.sub.4-C.sub.7 cycloalkylalkyl. [0147] Embodiment 12h. A compound of Embodiment 12g wherein R.sup.15 is H. [0148] Embodiment 12i. A compound of Embodiment 12g wherein R.sup.15 is C.sub.1-C.sub.6 alkyl. [0149] Embodiment 12j. A compound of Embodiment 12g wherein R.sup.15 is H, Me, Et, CH.sub.2CH?CH.sub.2 or CH.sub.2C?CH. [0150] Embodiment 12k. A compound of Embodiment 12j wherein R.sup.15 is Me, Et, CH.sub.2CH?CH.sub.2 or CH.sub.2C?CH. [0151] Embodiment 12l. A compound of Embodiment 12a wherein G and R.sup.5 are attached to the same carbon. [0152] Embodiment 12m. A compound of Embodiment 12l wherein R.sup.5 is H. [0153] Embodiment 12n. A compound of Embodiment 12a wherein G and R.sup.6 are attached to the same carbon. [0154] Embodiment 12o. A compound of Embodiment 12n wherein R.sup.6 is H. [0155] Embodiment 12p. A compound of Embodiment 12a wherein G and R.sup.7 are attached to the same carbon. [0156] Embodiment 12q. A compound of Embodiment 12p wherein R.sup.7 is H. [0157] Embodiment 12r. A compound of Embodiment 12a wherein G and R.sup.9 are attached to the same carbon. [0158] Embodiment 12s. A compound of Embodiment 12r wherein R.sup.9 is H. [0159] Embodiment 13. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycoalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.6 nitroalkyl, C.sub.3-C.sub.6 alkylcarboalkyl, C.sub.3-C.sub.6 alkoxycarboalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.3-C.sub.6 alkylcarboalkoxy; or [0160] R.sup.10 is selected from the group consisting of
##STR00011## ##STR00012## [0161] Embodiment 13a. A compound of Embodiment 13 wherein R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0162] Embodiment 13aa. A compound of Embodiment 13a wherein R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0163] Embodiment 13b. A compound of Embodiment 13aa wherein R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0164] Embodiment 13c. A compound of Embodiment 13b wherein R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0165] Embodiment 13d. A compound of Embodiment 13c wherein R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl or C.sub.4-C.sub.7 halocycloalkylalkyl. [0166] Embodiment 13dd. A compound of Embodiment 13d wherein R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.7 cycloalkyl. [0167] Embodiment 13e. A compound of Embodiment 13d wherein R.sup.10 is cyclopropyl, cyclobutyl, cyclopentyl, allyl or propargyl. [0168] Embodiment 13ee. A compound of Embodiment 13e wherein R.sup.10 is H. [0169] Embodiment 13f. A compound of Embodiment 13e wherein R.sup.10 is cyclopropyl. [0170] Embodiment 13g. A compound of Embodiment 13e wherein R.sup.10 is cyclobutyl. [0171] Embodiment 13gg. A compound of Embodiment 13e wherein R.sup.10 is cyclopentyl. [0172] Embodiment 13ggg. A compound of Embodiment 13e wherein R.sup.10 is cyclohexyl. [0173] Embodiment 13h. A compound of Embodiment 13e wherein R.sup.10 is allyl. [0174] Embodiment 13i. A compound of Embodiment 13e wherein R.sup.10 is propargyl. [0175] Embodiment 13j. A compound of Embodiment 13 wherein R.sup.10 is R.sup.10-1, R.sup.10-2, R.sup.10-3, R.sup.10-4, R.sup.10-5, R.sup.10-6, R.sup.10-7, R.sup.10-8, R.sup.10-9, R.sup.10-10, R.sup.10-11, R.sup.10-12, R.sup.10-13, R.sup.10-14, R.sup.10-15 or R.sup.10-16. [0176] Embodiment 13k. A compound of Embodiment 13j wherein R.sup.10 is R.sup.10-1, R.sup.10-2, R.sup.10-3, R.sup.10-4, R.sup.10-5, R.sup.10-6, R.sup.10-7, R.sup.10-8 or R.sup.10-9. [0177] Embodiment 13l. A compound of Embodiment 13k wherein R.sup.10 is R.sup.10-3 or R.sup.10-4. [0178] Embodiment 13m. A compound of Embodiment 13a wherein R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.4-C.sub.7 cycloalkylalkyl or benzyl. [0179] Embodiment 14. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.11 is H or C.sub.1-C.sub.7 alkyl. [0180] Embodiment 14a. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.11 is H. [0181] Embodiment 15. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.12 is H or C.sub.1-C.sub.7 alkyl. [0182] Embodiment 15a. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.12 is H. [0183] Embodiment 16. A compound of Formula 1 or any one of the preceding Embodiments wherein each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl. [0184] Embodiment 16a. A compound of Embodiment 16 wherein each R.sup.13 and R.sup.14 is independently C.sub.1-C.sub.4 alkyl. [0185] Embodiment 16b. A compound of Embodiment 16a wherein each R.sup.13 and R.sup.14 is independently C.sub.1-C.sub.3 haloalkyl. [0186] Embodiment 16c. A compound of Embodiment 16 wherein each R.sup.13 and R.sup.14 is independently CF.sub.3. [0187] Embodiment 17. A compound of Formula 1 or any one of the preceding Embodiments wherein R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0188] Embodiment 17a. A compound of Embodiment 28 wherein R.sup.f is CF.sub.3.
[0189] Embodiments of this invention, including Embodiments 1-17a above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments 1-17a above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
[0190] Combinations of Embodiments 1-17a are illustrated by: [0191] Embodiment A. A compound of Formula 1 as described in the Summary of the Disclosure wherein [0192] Q is direct bond; [0193] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0194] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0195] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0196] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0197] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0198] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0199] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0200] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0201] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0202] R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0203] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0204] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0205] each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and [0206] R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0207] Embodiment A1. A compound of Embodiment A wherein [0208] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0209] R.sup.2 is H, Me, F, Cl or CN; [0210] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0211] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0212] R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; [0213] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0214] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0215] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0216] G is OR.sup.10 or SR.sup.10; and [0217] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0218] Embodiment A2. A compound of Embodiment A1 wherein [0219] R.sup.1 is H, Me, halogen or cyclopropyl; [0220] R.sup.2 is H or F; [0221] R.sup.3 is Me or F; [0222] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0223] R.sup.5 is H; [0224] R.sup.6 is H, Me or OMe; [0225] R.sup.7 is H, Me or OMe; [0226] R.sup.8 is H, Me or OMe; [0227] G is OR.sup.10; and [0228] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0229] Embodiment A3. A compound of Embodiment A2 wherein [0230] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0231] R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; [0232] R.sup.8 is H; and [0233] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.7 cycloalkyl. [0234] Embodiment A4. A compound of Embodiment A3 wherein [0235] R.sup.1 is Me; [0236] R.sup.3 is Me; [0237] R.sup.4 is H; [0238] R.sup.6 is H; [0239] R.sup.7 is H; and [0240] R.sup.10 is cyclopropyl, cyclobutyl, cyclopentyl, allyl or propargyl. [0241] Embodiment B. A compound of Formula 1 as described in the Summary of the Disclosure wherein [0242] Q is CHR.sup.9; [0243] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0244] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0245] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0246] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0247] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0248] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0249] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0250] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0251] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0252] R.sup.9 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0253] R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0254] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0255] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0256] each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and [0257] R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0258] Embodiment B1. A compound of Embodiment B wherein [0259] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0260] R.sup.2 is H, Me, F, Cl or CN; [0261] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0262] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0263] R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; [0264] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0265] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0266] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0267] G is OR.sup.10 or SR.sup.10; [0268] R.sup.9 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; and [0269] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0270] Embodiment B2. A compound of Embodiment B1 wherein [0271] R.sup.1 is H, Me, halogen or cyclopropyl; [0272] R.sup.2 is H or F; [0273] R.sup.3 is Me or F; [0274] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0275] R.sup.5 is H; [0276] R.sup.6 is H, Me or OMe; [0277] R.sup.7 is H, Me or OMe; [0278] R.sup.8 is H, Me or OMe; [0279] G is OR.sup.10; [0280] R.sup.9 is H, Me or OMe; and [0281] R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0282] Embodiment B3. A compound of Embodiment B2 wherein [0283] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0284] R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; [0285] R.sup.8 is H; [0286] R.sup.9 is H; and [0287] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.7 cycloalkyl [0288] Embodiment C. A compound of Formula 1 as described in the Summary of the Disclosure wherein [0289] Q is O; [0290] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0291] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0292] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0293] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0294] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0295] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0296] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0297] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0298] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0299] R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0300] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0301] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0302] each R.sup.13 and R.sup.14 is independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and [0303] R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0304] Embodiment C1. A compound of Embodiment C wherein [0305] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0306] R.sup.2 is H, Me, F, Cl or CN; [0307] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0308] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0309] R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; [0310] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0311] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0312] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0313] G is OR.sup.10 or SR.sup.10; and [0314] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl, benzyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0315] Embodiment C2. A compound of Embodiment C1 wherein [0316] R.sup.1 is H, Me, halogen or cyclopropyl; [0317] R.sup.2 is H or F; [0318] R.sup.3 is Me or F; [0319] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0320] R.sup.5 is H; [0321] R.sup.6 is H, Me or OMe; [0322] R.sup.7 is H, Me or OMe; [0323] R.sup.8 is H, Me or OMe; [0324] G is OR.sup.10; and [0325] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0326] Embodiment C3. A compound of Embodiment C2 wherein [0327] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0328] R.sup.4 is H, CH.sub.2OCO-t-Bu or S(O).sub.2CF.sub.3; [0329] R.sup.8 is H; and [0330] R.sup.10 is C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl or C.sub.3-C.sub.7 cycloalkyl. [0331] Embodiment C4. A compound of Embodiment C3 wherein [0332] R.sup.1 is Me; [0333] R.sup.3 is Me; [0334] R.sup.4 is H; [0335] R.sup.6 is H; [0336] R.sup.7 is H; and [0337] R.sup.10 is cyclopropyl, cyclobutyl, cyclopentyl, allyl or propargyl. [0338] Embodiment D. A compound of Formula 1 as described in the Summary of the Disclosure wherein [0339] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0340] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0341] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0342] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0343] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0344] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0345] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0346] G and R.sup.5 are taken together to form NOR.sup.15; [0347] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0348] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0349] R.sup.13 and R.sup.14 are independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; [0350] R.sup.f is C.sub.1-C.sub.3 haloalkyl; and [0351] R.sup.15 is H, 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 alkynyl or C.sub.4-C.sub.7 cycloalkylalkyl. [0352] Embodiment D1. A compound of Embodiment D wherein [0353] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0354] R.sup.2 is H, Me, F, Cl or CN; [0355] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0356] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0357] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0358] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; and [0359] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy. [0360] Embodiment D2. A compound of Embodiment D1 wherein [0361] R.sup.1 is H, Me, halogen or cyclopropyl; [0362] R.sup.2 is H or F; [0363] R.sup.3 is Me or F; [0364] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0365] R.sup.6 is H, Me or OMe; [0366] R.sup.7 is H, Me or OMe; and [0367] R.sup.8 is H, Me or OMe. [0368] Embodiment D3. A compound of Embodiment D2 wherein [0369] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0370] R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; and [0371] R.sup.8 is H. [0372] Embodiment D4. A compound of Embodiment D3 wherein [0373] R.sup.1 is Me; [0374] R.sup.3 is Me; [0375] R.sup.4 is H; [0376] R.sup.6 is H; [0377] R.sup.7 is H; and [0378] R.sup.15 is H, Me, Et, CH.sub.2CH?CH.sub.2 or CH.sub.2C?CH. [0379] Embodiment D5. A compound of any one of Embodiments D to D4 wherein [0380] Q is direct bond. [0381] Embodiment P1. A compound selected from Formula 1, all stereoisomers, N-oxides, and salts thereof,
##STR00013## [0382] wherein [0383] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 haloalkynyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl or C.sub.2-C.sub.7 haloalkoxyalkyl; [0384] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 haloalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.5 alkylthio; [0385] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 haloalkynyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl or C.sub.2-C.sub.7 haloalkoxyalkyl; [0386] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; or propargyl, allyl or benzyl; [0387] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0388] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 haloalkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0389] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 haloalkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0390] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0391] Q is CHR.sup.9, O or a direct bond; [0392] R.sup.9 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.5 alkylthio, C.sub.2-C.sub.3 alkoxycarbonyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.7 haloalkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0393] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0394] R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.1-C.sub.6 nitroalkyl, C.sub.3-C.sub.6 alkylcarboalkyl, C.sub.3-C.sub.6 alkoxycarboalkyl or C.sub.3-C.sub.6 alkylcarboalkoxy; or [0395] R.sup.10 is selected from the group consisting of
##STR00014## ##STR00015## [0396] R.sup.11 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0397] R.sup.12 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.7 haloalkyl; [0398] each R.sup.13 and R.sup.14 are independently H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.3 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkylalkoxyalkyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.1-C.sub.7 alkoxy; C.sub.2-C.sub.7 alkoxyalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, Ph or benzyl; [0399] R.sup.f is C.sub.1-C.sub.7 haloalkyl; [0400] G and R.sup.8 can be attached to any ring carbon(s) with available valency, said ring is the cyclic amide ring shown in Formula 1; and [0401] each R.sup.11 or R.sup.12 can be attached to any ring carbon(s) with available valency, said ring is illustrated in R.sup.10-1 through R.sup.10-16 as above. [0402] Embodiment P2. The compound of Embodiment P1 wherein [0403] Q is direct bond; [0404] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0405] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0406] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0407] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0408] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0409] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0410] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0411] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0412] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0413] R.sup.10 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0414] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0415] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0416] R.sup.13 and R.sup.14 are independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and [0417] R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0418] Embodiment P3. The compound of Embodiment P2 wherein [0419] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0420] R.sup.2 is H, Me, F, Cl or CN; [0421] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0422] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0423] R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; [0424] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0425] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0426] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0427] G is OR.sup.10 or SR.sup.10; and [0428] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0429] Embodiment P4. The compound of Embodiment P3 wherein [0430] R.sup.1 is H, Me, halogen or cyclopropyl; [0431] R.sup.2 is H or F; [0432] R.sup.3 is Me or F; [0433] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0434] R.sup.5 is H; [0435] R.sup.6 is H, Me or OMe; [0436] R.sup.7 is H, Me or OMe; [0437] R.sup.8 is H, Me or OMe; [0438] G is OR.sup.10; [0439] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0440] Embodiment P5. The compound of Embodiment P4 wherein [0441] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0442] R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; [0443] R.sup.8 is H; and [0444] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.10 alkenylalkyl or C.sub.3-C.sub.10 alkynylalkyl. [0445] Embodiment P6. The compound of Embodiment P5 wherein [0446] R.sup.1 is Me; [0447] R.sup.3 is Me; [0448] R.sup.4 is H; [0449] R.sup.6 is H; [0450] R.sup.7 is H; and [0451] R.sup.10 is cyclopropyl, cyclobutyl, cyclopentyl, allyl or propargyl. [0452] Embodiment P7. The compound of Embodiment P6 wherein [0453] Q is CHR.sup.9; [0454] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0455] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0456] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0457] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0458] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0459] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0460] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0461] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0462] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0463] R.sup.9 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0464] R.sup.10 is alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0465] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0466] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0467] R.sup.13 and R.sup.14 are independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and [0468] R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0469] Embodiment P8. The compound of Embodiment P7 wherein [0470] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0471] R.sup.2 is H, Me, F, Cl or CN; [0472] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0473] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0474] R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; [0475] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0476] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0477] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0478] G is OR.sup.10 or SR.sup.10; [0479] R.sup.9 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0480] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0481] Embodiment P9. The compound of Embodiment P8 wherein [0482] R.sup.1 is H, Me, halogen or cyclopropyl; [0483] R.sup.2 is H or F; [0484] R.sup.3 is Me or F; [0485] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0486] R.sup.5 is H; [0487] R.sup.6 is H, Me or OMe; [0488] R.sup.7 is H, Me or OMe; [0489] R.sup.8 is H, Me or OMe; [0490] G is OR.sup.10; [0491] R.sup.9 is H, Me or OMe; [0492] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0493] Embodiment P10. The compound of Embodiment P9 wherein [0494] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0495] R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; [0496] R.sup.8 is H; [0497] R.sup.9 is H; and [0498] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.10 alkenylalkyl or C.sub.3-C.sub.10 alkynylalkyl. [0499] Embodiment P11. The compound of Embodiment P1 wherein [0500] Q is O; [0501] R.sup.1 is H, C.sub.1-C.sub.7 alkyl, halogen, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl; [0502] R.sup.2 is H, C.sub.1-C.sub.7 alkyl, halogen or CN; [0503] R.sup.3 is H, C.sub.1-C.sub.7 alkyl, halogen, CN, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkyl; [0504] R.sup.4 is H, C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, C(?O)NR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14 or CH.sub.2OC(?O)R.sup.14; [0505] R.sup.5 is H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0506] R.sup.6 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0507] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0508] R.sup.8 is H, C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 alkenylalkyl, C.sub.3-C.sub.7 alkynylalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0509] G is OR.sup.10, SR.sup.10, SOR.sup.10 or SO.sub.2R.sup.10; [0510] R.sup.10 is alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.4-C.sub.7 alkylcycloalkylalkyl, C.sub.1-C.sub.7 haloalkoxy, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 haloalkenyl, C.sub.3-C.sub.7 alkylthioalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl or C.sub.4-C.sub.7 alkylcycloalkyl; [0511] R.sup.11 is H or C.sub.1-C.sub.7 alkyl; [0512] R.sup.12 is H or C.sub.1-C.sub.7 alkyl; [0513] R.sup.13 and R.sup.14 are independently H, C.sub.1-C.sub.7 haloalkyl or C.sub.1-C.sub.7 alkyl; and [0514] R.sup.f is C.sub.1-C.sub.3 haloalkyl. [0515] Embodiment P12. The compound of Embodiment P11 wherein [0516] R.sup.1 is H, C.sub.1-C.sub.3 alkyl, halogen or C.sub.3-C.sub.4 cycloalkyl; [0517] R.sup.2 is H, Me, F, Cl or CN; [0518] R.sup.3 is H, Me, F, Cl, CN, OMe or CF.sub.3; [0519] R.sup.4 is H, SO.sub.2CF.sub.3, SO.sub.2CH.sub.3, CO.sub.2Me, COMe, CH.sub.2OCO-t-Bu, CH.sub.2OCO-n-Bu, CH.sub.2OCO-c-hexyl, CH.sub.2OCO-c-pentyl, CH.sub.2OCOCH.sub.2CH.sub.3, COMe, CH.sub.2OCOPh, CH.sub.2OCO-i-Bu, CH.sub.2OCOMe, CH.sub.2OCO-sec-Bu, CH.sub.2OCO-n-Pr and CH.sub.2OCO-i-Pr or (C?O)SMe; [0520] R.sup.5 is H, C.sub.4-C.sub.7 cycloalkylalkyl or C.sub.2-C.sub.7 alkoxyalkyl; [0521] R.sup.6 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0522] R.sup.7 is H, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.1-C.sub.7 alkoxy or C.sub.1-C.sub.7 haloalkoxy; [0523] R.sup.8 is H, C.sub.1-C.sub.7 alkyl or C.sub.1-C.sub.7 alkoxy; [0524] G is OR.sup.10 or SR.sup.10; [0525] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.10 alkylalkenylalkyl, C.sub.4-C.sub.10 alkylalkynylalkyl, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.4-C.sub.7 halocycloalkylalkyl, C.sub.5-C.sub.7 alkylcycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl, C.sub.2-C.sub.4 cyanoalkyl, C.sub.3-C.sub.7 alkylthioalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0526] Embodiment P13. The compound of Embodiment P12 wherein [0527] R.sup.1 is H, Me, halogen or cyclopropyl; [0528] R.sup.2 is H or F; [0529] R.sup.3 is Me or F; [0530] R.sup.4 is H, CH.sub.2OCOR.sup.14 or S(O).sub.2R.sup.14; [0531] R.sup.5 is H; [0532] R.sup.6 is H, Me or OMe; [0533] R.sup.7 is H, Me or OMe; [0534] R.sup.8 is H, Me or OMe; [0535] G is OR.sup.10; [0536] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.10 alkenylalkyl, C.sub.3-C.sub.10 alkynylalkyl, C.sub.4-C.sub.7 cycloalkylalkyl, C.sub.2-C.sub.7 alkoxyalkyl or C.sub.4-C.sub.7 alkylcycloalkyl. [0537] Embodiment P14. The compound of Embodiment P13 wherein [0538] R.sup.1 is H, Me, F, Cl, Br or cyclopropyl; [0539] R.sup.4 is H, CH.sub.2OCO-t-Bu or SO.sub.2CF.sub.3; [0540] R.sup.8 is H; and [0541] R.sup.10 is C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.10 alkenylalkyl or C.sub.3-C.sub.10 alkynylalkyl. [0542] Embodiment P15. The compound of Embodiment P14 wherein [0543] R.sup.1 is Me; [0544] R.sup.3 is Me; [0545] R.sup.4 is H; [0546] R.sup.6 is H; [0547] R.sup.7 is H; and [0548] R.sup.10 is cyclopropyl, cyclobutyl, cyclopentyl, allyl or propargyl. [0549] Specific embodiments include compounds of Formula 1 selected from the group consisting of:
TABLE-US-00001 N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]- 1,1,1-trifluoromethanesulfonamide (Compound 6); [[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 5) N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]- 1,1,1-trifluoromethanesulfonamide (Compound 1); N-[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]- 1,1,1-trifluoromethanesulfonamide (Compound 3); [[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 7); [[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 8); N-[2,4-dimethyl-5-[2-oxo-3-(2-propen-1-yloxy)-1-pyrrolidinyl]phenyl]- 1,1,1-trifluoromethanesulfonamide (Compound 2); and N-[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]- 1,1,1-trifluoromethanesulfonamide (Compound 4). N-[5-[3-(ethoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1- trifluoromethanesulfonamide (Compound 12) N-[2,4-dimethyl-5-[2-oxo-3-[(2-propyn-1-yloxy)imino]-1- pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide (Compound 13) 1,1,1-trifluoro-N-[5-[3-(methoxyimino)-2-oxo-1-pyrrolidinyl]-2,4- dimethylphenyl]methanesulfonamide (Compound 9)
[0550] This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for selective control of weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.
[0551] Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.
[0552] This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solanesyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts of compounds of (b1) through (b16).
[0553] Photosystem II inhibitors (b1) are chemical compounds that bind to the D-1 protein at the Q.sub.B-binding niche and thus block electron transport from Q.sub.A to Q.sub.B in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The Q.sub.B-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine.
[0554] AHAS inhibitors (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron.
[0555] ACCase inhibitors (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.
[0556] Auxin is a plant hormone that regulates growth in many plant tissues. Auxin mimics (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.
[0557] EPSP synthase inhibitors (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
[0558] Photosystem I electron diverters (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles leak, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.
[0559] PPO inhibitors (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, trifludimoxazin (dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione) and tiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-?-alaninate).
[0560] GS inhibitors (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.
[0561] VLCFA elongase inhibitors (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides.
[0562] Auxin transport inhibitors (b10) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).
[0563] PDS inhibitors (b11) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone norflurzon and picolinafen.
[0564] HPPD inhibitors (b12) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate), topramezone, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.
[0565] HST inhibitors (b13) disrupt a plant's ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.
[0566] HST inhibitors also include compounds of Formulae A and B.
##STR00016## [0567] wherein R.sup.d1 is H, Cl or CF.sub.3; R.sup.d2 is H, Cl or Br; R.sup.d3 is H or Cl; R.sup.d4 is H, Cl or CF.sub.3; R.sup.d5 is CH.sub.3, CH.sub.2CH.sub.3 or CH.sub.2CHF.sub.2; and R.sup.d6 is OH or OC(?O)-i-Pr; and R.sup.e1 is H, F, Cl, CH.sub.3 or CH.sub.2CH.sub.3; R.sup.e2 is H or CF.sub.3; R.sup.e3 is H, CH.sub.3 or CH.sub.2CH.sub.3; R.sup.e4 is H, F or Br; R.sup.e5 is Cl, CH.sub.3, CF.sub.3, OCF.sub.3 or CH.sub.2CH.sub.3; R.sup.e6 is H, CH.sub.3, CH.sub.2CHF.sub.2 or C?CH; R.sup.e7 is OH, OC(?O)Et, OC(?O)-i-Pr or OC(?O)-t-Bu; and A.sup.e8 is N or CH.
[0568] Cellulose biosynthesis inhibitors (b14) inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied preemergence or early postemergence on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N.sup.2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben and triaziflam.
[0569] Other herbicides (b15) include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl) organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors. Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (b1) through (b14) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.
[0570] Other herbicides (b15) also include a compound of Formula (b15A)
##STR00017## [0571] wherein [0572] R.sup.12 is H, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl or C.sub.4-C.sub.8 cycloalkyl; [0573] R.sup.13 is H, C.sub.1-C.sub.6 alkyl or C.sub.1-C.sub.6 alkoxy; [0574] Q.sup.1 is an optionally substituted ring system selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl and pyrazolyl, wherein when substituted said ring system is substituted with 1 to 3 R.sup.14; [0575] Q.sup.2 is and optionally substituted ring system selected from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, wherein when substituted said ring system is substituted with 1 to 3 R.sup.15; [0576] each R.sup.14 is independently halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.3-C.sub.8 cyaloalkyl, cyano, C.sub.1-C.sub.6 alkylthio, C.sub.1-C.sub.6 alkylsulfinyl, C.sub.1-C.sub.6 alkylsulfonyl, SF.sub.5, NHR.sup.17; or phenyl optionally substituted by 1 to 3 R.sup.16; or pyrazolyl optionally substituted by 1 to 3 R.sup.16; [0577] each R.sup.15 is independently halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, cyano, nitro, C.sub.1-C.sub.6 alkylthio, C.sub.1-C.sub.6 alkylsulfinyl, C.sub.1-C.sub.6 alkylsulfonyl; [0578] each R.sup.16 is independently halogen, C.sub.1-C.sub.6 alkyl or C.sub.1-C.sub.6 haloalkyl; and [0579] R.sup.17 is C.sub.1-C.sub.4 alkoxycarbonyl.
[0580] In one Embodiment wherein other herbicides (b15) also include a compound of Formula (b15A), it is preferred that R.sup.12 is H or C.sub.1-C.sub.6 alkyl; more preferably R.sup.12 is H or methyl. Preferrably R.sup.13 is H. Preferably Qi is either a phenyl ring or a pyridinyl ring, each ring substituted by 1 to 3 R.sup.14; more preferably Q.sup.1 is a phenyl ring substituted by 1 to 2 R.sup.14.
[0581] Preferably Q.sup.2 is a phenyl ring substituted with 1 to 3 R.sup.15; more preferably Q.sup.2 is a phenyl ring substituted by 1 to 2 R.sup.15. Preferably each R.sup.14 is independently halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy or C.sub.1-C.sub.3 haloalkoxy; more preferably each R.sup.14 is independently chloro, fluoro, bromo, C.sub.1-C.sub.2 haloalkyl, C.sub.1-C.sub.2 haloalkoxy or C.sub.1-C.sub.2 alkoxy. Preferrably each R.sup.15 is independently halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.3 haloalkoxy; more preferably each R.sup.15 is independently chloro, fluoro, bromo, C.sub.1-C.sub.2 haloalkyl, C.sub.1-C.sub.2 haloalkoxy or C.sub.1-C.sub.2 alkoxy.
[0582] Specifically preferred as other herbicides (b15) include any one of the following (b15A-1) through (b15A-15):
##STR00018## ##STR00019## ##STR00020##
[0583] Other herbicides (b15) also include a compound of Formula (b15B)
##STR00021## [0584] wherein [0585] R.sup.18 is H, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl or C.sub.4-C.sub.8 cycloalkyl; [0586] each R.sup.19 is independently halogen, C.sub.1-C.sub.6 haloalkyl or C.sub.1-C.sub.6 haloalkoxy; [0587] p is an integer of 0, 1, 2 or 3; [0588] each R.sup.20 is independently halogen, C.sub.1-C.sub.6 haloalkyl or C.sub.1-C.sub.6 haloalkoxy; and [0589] q is an integer of 0, 1, 2 or 3.
[0590] In one Embodiment wherein other herbicides (b15) also include a compound of Formula (b15B), it is preferred that R.sup.18 is H, methyl, ethyl or propyl; more preferably R.sup.18 is H or methyl; most preferably R.sup.18 is H. Preferrably each R.sup.19 is independently chloro, fluoro, C.sub.1-C.sub.3 haloalkyl or C.sub.1-C.sub.3 haloalkoxy; more preferably each R.sup.19 is independently chloro, fluoro, C.sub.1 fluoroalkyl (i.e. fluoromethyl, difluoromethyl or trifluoromethyl) or C.sub.1 fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy). Preferably each R.sup.20 is independently chloro, fluoro, C.sub.1 haloalkyl or C.sub.1 haloalkoxy; more preferably each R.sup.20 is independently chloro, fluoro, C.sub.1 fluoroalkyl (i.e. fluoromethyl, difluoromethyl or trifluromethyl) or C.sub.1 fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy).
[0591] Specifically preferred as other herbicides (b15) include any one of the following (b15B-1) through (b15B-19):
##STR00022## ##STR00023## ##STR00024## ##STR00025##
[0592] Another Embodiment wherein other herbicides (b15) also include a compound of Formula (b15C),
##STR00026##
[0593] wherein R.sup.1 is Cl, Br or CN; and R.sup.2 is C(?O)CH.sub.2CH.sub.2CF.sub.3, CH.sub.2CH.sub.2CH.sub.2CH.sub.2CF.sub.3 or 3-CHF.sub.2-isoxazol-5-yl.
[0594] Herbicide safeners (b16) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide.
[0595] One or more of the following methods and variations as described in Schemes 1-13 can be used to prepare the compounds of Formula 1. The definitions of G, Q, X, R.sup.1-R.sup.10, and R.sup.f in the compounds of Formulae 1-19 below are as defined above in the Summary of the Disclosure unless otherwise noted. Compounds of Formulae 1a, 1b, 1c, 1d, 3a, 4a, 4b, 4c, 5a and 5b are various subsets of the compounds of Formulae 1, 3, 4 and 5; and all substituents for Formulae 1a, 1b, 1c, 1d, 3a, 4a, 4b, 4c, 5a and 5b are as defined above for Formula 1 unless otherwise noted in the disclosure including the schemes.
[0596] As outlined in Scheme 1, compounds of Formula 1a (i.e a compound of Formula 1, wherein R.sup.4 is H) can be made by reaction of an appropriately substituted aniline of Formula 2 with 1 equivalent (or a slightly excess over 1 equivalent) of a haloalkylsulfonyl chloride of Formula R.sup.fSO.sub.2Cl or a corresponding haloalkylsulfonyl anhydride of Formula R.sup.f(SO.sub.2).sub.2O in the presence of a suitable base, in a compatible solvent including but not limited to tetrahydrofuran, acetonitrile, toluene, diethyl ether, dioxane, dichloromethane or N,N-dimethylformamide, at temperatures generally ranging from 0? C. to ambient temperature. Some examples of the suitable base can be pyridine, triethylamine, Hunig's base or potassium carbonate. Alternatively, bis-sulfonamides of Formula 1b (i.e a compound of Formula 1, wherein R.sup.4 is SO.sub.2R.sup.f and R.sup.f is haloalkyl) are accessible by reacting an aniline of Formula 2 with 2 equivalents (or an excess over 2.0 equivalents) of a haloalkylsulfonyl chloride of Formula R.sup.fSC.sub.2Cl or a corresponding haloalkylsulfonyl anhydride of Formula R.sup.f(SO.sub.2).sub.2O under similar reaction conditions described as above. Treating bis-sulfonamides of Formula 1b with an excess of aqueous base followed by neutralization or acidification with acid readily provides the corresponding mono-sulfonamide of Formula 1a. Preferred conditions for this hydrolysis are usually aqueous sodium or potassium hydroxide, optionally used with a cosolvent such as methanol, ethanol, dioxane or tetrahydrofuran, followed by neutralization or acidification with concentrated or aqueous hydrochloric acid.
##STR00027##
[0597] Substituted anilines of Formula 2 are readily accessed by hydrogenation of nitrobenzenes of Formula 3 under conditions that include but not limited to catalytic hydrogenation with 5-10% palladium metal on carbon or platinum oxide in solvents such as methanol, ethanol or ethyl acetate under an atmosphere of hydrogen. This reaction can generally be done in a Parr Hydrogenator. Alternatively, reduction of the nitro group can be accomplished with activated zinc metal in acetic acid, with stannous chloride in aqueous hydrochloric acid, iron metal in acetic acid or in aqueous alcohol or in an aqueous ethyl acetate mixture with ammonium chloride (i.e. Fe with 3 equivalents of ammonium chloride in aqueous ethanol) or with sodium borohydride in methanol in the presence of NiAC.sub.2-4H.sub.2O (see J. Am. Chem. Soc., 2005, 119).
##STR00028##
[0598] Intermediates of Formula 3 can be accessed by copper-mediated coupling of a meta-bromo or meta-iodo substituted nitrobenzene of Formula 4a or 4b (wherein X is bromine for 4a and X is iodine for 4b) with a cyclic amide of Formula 5 in the presence of copper (I) iodide with a diamine ligand, e.g. trans-N,N-Dimethylcyclohexane-1,2-diamine or tetramethylethylenediamine (TMEDA), and potassium phosphate (K.sub.3PO.sub.4) in an appropriate solvent. The solvent can be, for example, N,N-dimethylformamide, acetonitrile, tetrahydrofuran or dioxane, optionally with water as a cosolvent. A similar copper-mediated coupling can also be carried out under Chan-Lam conditions where a boronic acid of Formula 4c (i.e. a compound of Formula 4 wherein X is B(OH).sub.2) is coupled with a compound of Formula 5 in the presence of copper II acetate (Cu(II)AC.sub.2) and pyridine in dichloromethane. Alternatively, this cross-coupling can also be carried out with a compound of Formula 4c and a compound for Formula 5 under the well-documented Buchwald-Hartwig amination protocol involving palladium-mediation with a suitable phosphine ligand, either as part of the pre-catalyst or as an additive in an appropriate solvent such as tetrahydrofuran, toluene or dichloromethane. In some cases, an auxiliary base, i.e. sodium tert-butoxide or cesium carbonate, is used in the reaction. Examples of palladium catalysts suitable for this transformation include but are not limited to tetrakis(triphenylphosphine) palladium(0) [Pd(PPh.sub.3).sub.4], bistriphenylphosphine palladium chloride [PdCl.sub.2(PPh.sub.3).sub.2], palladium(II) chloride-tris(2-methylphenyl)phosphine [PdCl.sub.2[P(o-Tol).sub.3].sub.2] or [1,1bis(diphenylphosphino) ferrocene] dichloropalladium(II) [Pd(dppf)Cl.sub.2]. Finally, this cross-coupling can also be accomplished with palladium acetate [Pd(OAc).sub.2] or tris(dibenzylideneacetone) dipalladium(0) [Pd.sub.2(dba)] optionally used in combination with a suitable phosphine ligand with a base such as sodium tert-butoxide in toluene or cesium carbonate in N,N-dimethylformamide.
##STR00029##
[0599] As illustrated in Scheme 4, nitrobenzenes of Formula 4 can be prepared by nitration of a substituted benzene of Formula 6 in a mixture of nitric acid and sulfuric acid at temperatures ranging from 0? C. to ambient temperature to afford nitrobenzenes of Formula 4. Other sources of nitronium ion for this nitration include nitronium tetrafluoroborate, acetyl nitrate, guanidinium nitrate, used in an appropriate solvent such as tetramethylene sulfone. Substituted benzenes of Formula 6 are, in some cases, commercially available and in other cases readily prepared by established methods from the literature. It is recognized that nitration of some substituted benzenes of Formula 6 can give rise to regioisomeric mixture of nitrobenzenes that require separation by chromatography or fractional crystallization techniques.
##STR00030##
[0600] Alternatively, a nitrobenzene of Formula 4a (i.e. a compound of Formula 4 wherein X is bromine) or a nitrobenzene of Formula 4b (i.e. a compound of Formula 4 wherein X is idodine) can be prepared by halogenation of a substituted nitrobenzene of Formula 7 with an appropriate halogenating reagent, such as bromine, iodine, N-bromosuccinimide or N-iodosuccinimide, in an appropriate solvent, such as acetic acid, dichloromethane, carbon tetrachloride, chloroform, acetonitrile or N,N-dimethylformamide by established methods as shown in Scheme 5. Iodobenzenes of Formula 4b can also be made from benzenes of Formula 7 by treating with 2,2,6,6-tetramethylpiperidylzincchloride-LiCl (TMPZnCl.Math.LiCl) in tetrahydrofuran or dioxane, followed by the addition of iodine and a mixture of nitric acid and sulfuric acid at temperatures ranging from 0? C. to ambient temperature. Bromo and iodo benzenes of Formulae 4a and 4b can be lithiated with an alkyl lithium reagent, preferably n-butyl lithium, in tetrahydrofuran or dioxane typically at temperatures generally ranging from ?78? C. to 0? C., followed by addition of trimethyl boroxine and subsequent acidic hydrolysis to afford the corresponding aryl boronic acids of Formula 4c (i.e. a compound of Formula 4 wherein X is B(OH).sub.2). Conversion of aryl halides to aryl boronic acids is a well-established synthetic transformation in the organic chemistry literature.
##STR00031##
[0601] As shown in Scheme 6, a cyclic amide of Formula 5a can be made from hydroxy-substituted N-protected cyclic amides of Formula 8, where PG represents a protecting group such as a Cbz (benzyloxycarbonyl) or BOC (tert-butyloxycarbonyl) group. Alkylating the compound of Formula 8 with an appropriate alkylating agent, in the presence of a base, such as sodium hydride, potassium tert-butoxide or sodium methoxide, in a solvent like tetrahydrofuran or dioxane at temperatures generally ranging from 0? C. to reflux temperature of the solvent affords a compound of Formula 9. The N-protecting group CBZ can then be removed by catalytic hydrogenation (generally under hydrogen in the presence of palladium-on-carbon in methanol or ethanol) to give a compound of Formula 5a. The N-protecting group BOC can be removed by trifluoroacetic acid to provide a compound of Formula 5a. Intermediate cyclic amides of Formula 9 can also be made from cyclic amides of Formula 10 where LG represents an appropriate leaving group such as a halogen (i.e. chlorine, bromine or iodine) or mesylate. Reacting a compound of Formula 10 with a nucleophile of Formula R.sup.10OH, in the presence of a base such as sodium hydride, potassium tert-butoxide or sodium methoxide, in a solvent such as tetrahydrofuran or dioxane at temperatures generally ranging from 0? C. to reflux temperature of the solvent afford a compound of Formula 9.
##STR00032##
[0602] A compound of Formula 3a (i.e. a compound of Formula 3, wherein G is OR.sup.10) can also be accessed by the synthetic route outlined in Scheme 7. Cross-coupling of a meta-bromo or meta-iodo substituted nitrobenzene of Formula 4a or 4b (i.e. a compound of Formula 4, wherein X is bromine or iodine) with a hydroxy-substituted cyclic amide of Formula 11 by the same methods described for the cross-coupling in Scheme 3, affords a compound of Formula 12 with a free hydroxy group. Alkylation of 12 with an appropriate alkylating agent in the presence of a base such as sodium hydride, potassium tert-butoxide or sodium methoxide in a solvent such as tetrahydrofuran or dioxane at temperatures generally ranging from 0? C. to reflux temperature of the solvent, gives a compound of Formula 3a. Alternatively, a compound of Formula 3a can be made in some cases by the method outlined in Scheme 8. Cross-coupling of an unprotected cyclic amide of Formula 13 with a substituted nitrobenzene of Formula 4 under the same cross-coupling conditions as described in Scheme 3, can give a compound of Formula 14. The unprotected cyclic amide of Formula 13 contains both a suitable leaving group LG, wherein LG is bromine, chlorine or iodine, and a free amide NH group. Displacement of the leaving group LG on 14 with a sodium or potassium alkoxide (NaOR.sup.10 or KOR.sup.10) in a suitable solvent such as tetrahydrofuran, dioxane, methanol, ethanol, dimethylsulfoxide or N,N-dimethylforamide provides a compound of Formula 3a.
##STR00033##
##STR00034##
[0603] Alternatively, a compound of Formula 3b (i.e. a compound of Formula 3, wherein G is SR.sup.10) can be made as outlined in Scheme 9. Displacement of the leaving group LG on a compound of Formula 14 with a sodium or potassium thiol reagent (NaSR.sup.10 or KSR.sup.10) in a suitable solvent such as tetrahydrofuran, dioxane, acetonitrile or N,N-dimethylformamide at temperatures ranging 0? C. to the reflux temperature of the solvent can afford a compound of Formula 3b. Oxidation of the sulfur with an appropriate oxidizing agent such as meta-chloroperoxybenzoic (MCPBA), sodium periodate or Oxone can provide the corresponding sulfoxide (SOR.sup.10) and sulfone (SO.sub.2R.sup.10).
##STR00035##
[0604] A method for making a compound of Formula 5b (i.e. a compound of Formula 5 wherein X is O) or a compound of Formula 5c (i.e. a compound of Formula 5 wherein X is S) is outlined in Scheme 10. Based on a known method (see Eur. J. Org. Chem. 2020, 3013-3018), heating a BOC (tert-butyloxycarbonyl)-protected cyclic amide of Formula 15 with t-butoxy bis-(dimethylamino)methane in toluene or xylene at the reflux temperature gives the corresponding enamine adduct 16. A compound of 16 can be reacted with sodium azide in the presence of chlorosulfonyl benzoic acid and potassium carbonate, in aqueous acetonitrile, to generate the diazo compound 17. A compound of Formula 17 can undergo a rhodium-catalyzed carbenoid insertion into an alcohol (R.sup.10OH) OH bond or thiol (R.sup.10SH)SH bond to generate an OR.sup.10 or SR.sup.10 substituted BOC-protected cyclic amide of Formula 18b wherein X is O or Formula 18c wherein X is S. Removal of the BOC-protecting group under acidic conditions, generally in trifluoroacetic acid, gives the free cyclic amide of Formula 5b wherein X is O or Formula 5c wherein X is S. This is a particularly useful method for introducing OR.sup.10 and SR.sup.10 groups where the R.sup.10 moiety may be a branched-chain, cyclic or bulky substituent.
##STR00036##
[0605] Compounds of Formula 1 where R.sup.4 is C(?O)R.sup.14, C(?S)R.sup.14, CO.sub.2R.sup.14, C(?O)SR.sup.14, S(O).sub.2R.sup.14, CONR.sup.13R.sup.14, S(O).sub.2NR.sup.13R.sup.14, CH.sub.2OC(?O)NR.sup.13R.sup.14, CH.sub.2OC(?O)OR.sup.14 or CH.sub.2O(C?O)R.sup.14 can be made by reaction of a sulfonanilide of Formula 1 where R.sup.4 is hydrogen with an appropriately substituted acyl halide, thioacyl halide, carbamoyl halide, sulfonyl halide, sulfamoyl halide, acyloxymethyl halide (i.e. ClCH.sub.2O(C?O)R.sup.14) or a similar halide, or other capping agents in the presence of a base such as triethylamine, pyridine, diisopropylethyl amine (Hunig's Base) or potassium carbonate in a solvent including but not limited to tetrahydrofuran, dioxane, dichloromethane, acetonitrile or N,N-dimethylformamide (Scheme 11).
##STR00037##
[0606] Compounds of Formula 1c (i.e. a compound of Formula 1 where R.sup.4 is H, and G and R.sup.5 are taken together to form NOR.sup.15 where R.sup.15 is not H) can be prepared by treatment of a compound of Formula 1d (i.e. a compound of Formula 1 where R.sup.4 is H, and G and R.sup.5 are taken together to form NOH) with an appropriate alkylating agent, in the presence of a base such as potassium tert-butoxide or sodium hydride, in a solvent like tetrahydrofuran at temperatures generally ranging from 0? C. to the reflux temperature of the solvent.
##STR00038##
[0607] Compounds of Formula 1d (i.e. a compound of Formula 1 where R.sup.4 is H, and G and R.sup.5 are taken together to form NOH) can be prepared by treatment of a compound of Formula 19, with a strong base such as, but not limited to sodium bis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide or lithium diisopropylamide and a nitrosylating agent, for example an alkyl nitrite such as, but not limited to isopentyl nitrite or tert-butyl nitrite. The reactions are typically performed in a solvent such as tetrahydrofuran at temperatures ranging from approximately ?78? C. to 50? C. Representative examples may be found in Chem. Pharm. Bull. 1986, vol. 34, pp. 2732-2742 and Org. Lett. 2021, vol. 23, pp. 5394-5399. Compounds of Formula 19 can be prepared using the preceding description.
##STR00039##
[0608] It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. For example, intermediates for the preparation of compounds of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing compounds of Formula 1. The above reactions can also in many cases be performed in alternate order.
[0609] It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.
[0610] One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.
[0611] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting Examples are illustrative of the invention. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. .sup.1H NMR spectra are reported in ppm downfield from tetramethylsilane; s means singlet, d means doublet, t means triplet, q means quartet, m means multiplet, dd means doublet of doublets, ddd means doublet of doublets of doublets, dt means doublet of triplets, and br s means broad singlet. Mass spectra (MS) are reported as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H+(molecular weight of 1) to the molecule or (M?1) formed by the loss of H+(molecular weight of 1) from the molecule, observed by using liquid chromatography coupled to a mass spectrometer (LCMS) using either atmospheric pressure chemical ionization (AP+) where amu stands for unified atomic mass units.
[0612] The following non-limiting Examples are meant to be illustrative of the present processes for preparing compounds of Formula 1 and corresponding intermediates. All NMR spectra are reported in CDCl.sub.3 at 500 MHz downfield from tetramethyl silane unless otherwise indicated.
Synthesis Example 1
Preparation of [[5-[3-(Cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (Compound 5)
Step A: Preparation of tert-butyl 3-(cyclopentoxy)-2-oxo-pyrrolidine-1-carboxylate
[0613] To a solution of tert-butyl 3-diazo-2-oxopyrolidine-1-carboxylate (300 mg, 1.42 mmol) and cyclopentanol (0.26 mL, 2.84 mmol) in dichloromethane (5 mL) was added dirhodium tetraacetate (19 mg, 3 mol %). The mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The residue was purified by column chromatography (0-60% ethyl acetate in hexanes gradient on silica) to afford the desired product (342 mg) as a clear oil.
[0614] .sup.1H NMR (CDCl.sub.3) ? 1.53 (s, 9H), 1.55-1.62 (m, 4H), 1.71-1.82 (m, 4H), 1.86-1.98 (m, 1H) 2.23-2.29 (m, 1H), 3.52 (ddd, J=10.92, 8.08, 7.17 Hz, 1H), 3.79 (ddd, J=10.88, 8.51, 3.78 Hz, 1H), 4.05 (t, J=7.88 Hz, 1H), 4.36-4.41 (m, 1H).
Step B: Preparation of 3-(cyclopentoxy)pyrrolidin-2-one
[0615] To a solution of tert-butyl 3-(cyclopentoxy)-2-oxo-pyrrolidine-1-carboxylate (i.e. the product of Step A) (342 mg, 1.27 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.29 mL, 3.81 mmol). The reaction mixture was stirred at room temperature for 2 h before quenched with NaHCO.sub.3 (aq.) and extracted with dichloromethane. Combined organic layers were dried with magnesium sulfate and concentrated under reduced pressure to afford 3-(cyclopentoxy)pyrrolidin-2-one (191 mg) as a clear oil and used without further purification.
[0616] .sup.1H NMR (CDCl.sub.3) ? 1.48-1.62 (m, 4H), 1.64-1.86 (m, 4H), 2.01-2.10 (m, 1H), 2.37-2.46 (m, 1H), 3.27 (dt, J=9.50, 7.23 Hz, 1H), 3.41 (td, J=8.99, 3.63 Hz, 1H), 4.02 (t, J=7.49 Hz, 1H), 4.30-4.38 (m, 1H), 6.03 (br s, 1H).
Step C: Preparation of 3-(cyclopentoxy)-1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidin-2-one
[0617] To a 25 mL scintillation vial with septum, copper(I) iodide (45 mg, 25 mol %), potassium carbonate (390 mg, 2.82 mmol), 3-(cyclopentoxy)pyrrolidin-2-one (i.e. the product of Step B) (191 mg, 1.13 mmol) and 1-bromo-2,4-dimethyl-5-nitrobezene (216 mg, 0.94 mmol) were added. The reaction vial was purged with nitrogen gas before dioxane (5 mL) and trans-N,N-dimethyl-cyclohexane-1,2-diamine (0.074 mL, 50 mol %) were added to the reaction vial via syringe. The reaction mixture was stirred under nitrogen at 100? C. overnight, then diluted with ethyl acetate and filtered through a pad of Celite? diatomaceous earth filter aid. The resulting filtrate was dried over magnesium sulfate and concentrated under reduced pressure to a residue. The residue was purified by column chromatography (0-60% ethyl acetate in hexanes gradient on silica) to afford the desired product (279 mg) as a clear oil.
[0618] .sup.1H NMR (CDCl.sub.3) ?:1.49-1.61 (m, 3H), 1.67-1.86 (m, 5H), 2.17 (ddt, J=13.00, 8.04, 6.42, 6.42 Hz, 1H), 2.27 (s, 3H), 2.46-2.54 (m, 1H), 2.60 (s, 3H), 3.64 (ddd, J=9.65, 7.29, 6.38 Hz, 1H), 3.73 (ddd, J=9.62, 8.04, 4.57 Hz, 1H), 4.18-4.21 (m, 1H), 4.38-4.49 (m, 1H), 7.24 (s, 1H), 7.86 (s, 1H)
Step D: Preparation of 1-(5-amino-2,4-dimethyl-phenyl)-3-(cyclopentoxy)pyrrolidin-2-one
[0619] To a stirred solution of 3-(cyclopentoxy)-1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidin-2-one (i.e. the product of Step C) (278 mg, 0.87 mmol) in ethyl acetate (4 mL) was added a solution of ammonium chloride (93 mg, 1.75 mmol) in water (1 mL). Iron powder (146 mg, 2.62 mmol) was then added and stirred at 80? C. under nitrogen overnight. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through a pad of Celite? diatomaceous earth filter aid. The filtrate was concentrated under reduced pressure to afford the title compound (275 mg) and used without further purification.
[0620] .sup.1H NMR (CDCl.sub.3) ? 1.42-1.62 (m, 3H), 1.66-1.86 (m, 5H), 2.04-2.25 (m, 7H), 2.38-2.51 (m, 1H), 3.53 (ddd, J=9.77, 7.41, 6.46 Hz, 1H), 3.65 (ddd, J=9.81, 8.16, 4.41 Hz, 1H), 4.16-4.18 (m, 1H), 4.37-4.53 (m, 1H), 6.48 (s, 1H) 6.92 (s, 1H).
Step E: Preparation of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
[0621] To a stirred solution of 1-(5-amino-2,4-dimethyl-phenyl)-3-(cyclopentoxy)pyrrolidin-2-one (i.e. the product of Step D) (275 mg, 0.95 mmol) in dichloromethane (4.8 mL) was added triethylamine (0.279 mL, 2.00 mmol). The mixture was cooled to ?78? C., then trifluoromethanesulfonic anhydride (0.34 mL, 2.00 mmol) was added dropwise. The reaction mixture was then stirred at room temperature for 1 h before quenched with aqueous NaHCO.sub.3 solution and extracted with dichloromethane. The combined organic layers were dried with magnesium sulfate, concentrated under reduced pressure and purified by column chromatography (0-60% ethyl acetate in hexanes gradient on silica) to afford the title compound (380 mg).
[0622] .sup.1H NMR (CDCl.sub.3) ? 1.50-1.61 (m, 3H), 1.68-1.89 (m, 5H), 2.16 (ddt, J=13.10, 8.18, 6.54, 6.54 Hz, 1H), 2.25 (s, 3H), 2.39 (s, 3H), 2.45-2.55 (m, 1H), 3.56-3.63 (m, 1H), 3.66-3.73 (m, 1H), 4.20 (dd, J=7.41, 6.62 Hz, 1H), 4.43 (tt, J=5.87, 3.59 Hz, 1H), 7.08 (s, 1H), 7.26 (s, 1H).
Step F: Preparation of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide
[0623] To a stirred solution of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (i.e. the product of Step E) (380 mg, 0.69 mmol) in dioxane (6.8 mL) was added 1 N aqueous sodium hydroxide solution (0.72 mL, 0.72 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 h, then neutralized with 1 N aqueous hydrogen chloride solution and extracted with dichloromethane. The combined organic layers were dried with magnesium sulfate, concentrated under reduced pressure and purified by column chromatography (0-50% ethyl acetate in hexanes gradient, on silica) to afford the title compound (160 mg) as a white solid.
[0624] .sup.1H NMR (CDCl.sub.3) ? 1.50-1.60 (m, 2H), 1.65-1.86 (m, 6H), 2.12-2.19 (m, 7H), 2.43-2.52 (m, 1H), 3.54 (ddd, J=10.01, 7.49, 6.46 Hz, 1H), 3.66 (ddd, J=10.01, 8.28, 4.41 Hz, 1H), 4.24 (dd, J=7.72, 6.31 Hz, 1H), 4.46-4.53 (m, 1H), 6.87 (s, 1H), 7.03 (s, 1H), 8.65 (br s, 1H).
Step G: Preparation of [[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate
[0625] To a stirred solution of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (i.e. the product of Step F) (70 mg, 0.17 mmol) in dichloromethane (5 mL) was added triethylamine (0.058 mL, 0.42 mmol) and chloromethyl 2,2-dimethylpropanoate (0.048 mL, 0.33 mmol). The reaction mixture was stirred overnight at 45-50? C. before concentrated under reduced pressure. The residue was purified by column chromatography (0-100% ethyl acetate in hexane gradient, on silica) to afford the title compound (75 mg) as a clear oil.
[0626] .sup.1H NMR (CDCl.sub.3) ? 1.20 (d, J=3.63 Hz, 9H), 1.50-1.60 (m, 2H), 1.66-1.87 (m, 6H), 2.10-2.18 (m, 1H), 2.21 (d, J=9.62 Hz, 3H), 2.38 (s, 3H), 2.41-2.52 (m, 1H), 3.52-3.57 (m, 1H), 3.64-3.75 (m, 1H), 4.13-4.18 (m, 1H), 4.41-4.45 (m, 1H), 5.42 (t, J=10.64 Hz, 1H), 5.70 (t, J=11.59 Hz, 1H), 7.05 (d, J=17.50 Hz, 1H), 7.22 (s, 1H).
Synthesis Example 2
Preparation of N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide (Compound 1)
Step A: Preparation of 1-(2,4-dimethyl-5-nitro-phenyl)-3-hydroxy-pyrrolidin-2-one
[0627] To a solution of 1-bromo-2,4-dimethyl-5-nitrobezene (2.50 g, 10.86 mmol) in 1, 4-dioxane (20 mL) was added 3-hydroxypyrrolidin-2-one (2.74 g, 27.17 mmol), K.sub.2CO.sub.3 (4.50 g, 32.60 mmol), copper(I) iodide (2.06 g, 10.86 mmol) and N,N-Dimethylethylenediamine (DMEDA) (2.3 mL, 21.73 mmol) at room temperature. The reaction mixture was degassed under N.sub.2 for 10 min and then stirred at 110? C. for 16 h. The reaction mixture was filtered through Celite? diatomaceous earth filter aid and washed with ethyl acetate (50 mL). The filtrate was evaporated under reduced pressure and triturated with n-pentane (25 mL), and diethyl ether (5 mL) to give the desired product (2.2 g) as off-white solid.
[0628] .sup.1H NMR (CDCl.sub.3) ? 7.87 (s, 1H), 7.26 (s, 1H), 5.54-4.99 (t, 1H), 3.76-3.65 (m, 2H), 2.94 (br, 1H), 2.66-2.63 (m, 1H), 2.60 (s, 3H), 2.27 (s, 3H), 2.26-2.20 (m, 1H).
Step B: Preparation of 1-(2,4-dimethyl-5-nitro-phenyl)-3-prop-2-ynoxy-pyrrolidin-2-one
[0629] To a solution of 1-(2,4-dimethyl-5-nitro-phenyl)-3-hydroxy-pyrrolidin-2-one (i.e. the product of Step A) (1.5 g, 6 mmol) in THF (30 mL) was added NaH (0.432 g, 18 mmol, 60%) and propargyl bromide (1.36 mL, 18 mmol) at 0? C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with saturated aqueous NH.sub.4Cl solution (10 mL) and extracted with ethyl acetate (25 mL?2). Combined organic layers were dried over anhydrous Na.sub.2SO.sub.4. The solvent was concentrated under reduced pressure to give the crude product. The cruder product was charged on silica gel column. Elution of the column with 30% ethyl acetate/petroleum ether gave the desired product (500 mg) as a light yellow solid.
[0630] LCMS (M+1)=289.
Step C: Preparation of 1-(5-amino-2,4-dimethylphenyl)-3-(2-propyn-1-yloxy)-2-pyrrolidinone
[0631] To a solution of 1-(2,4-dimethyl-5-nitro-phenyl)-3-prop-2-ynoxy-pyrrolidin-2-one (i.e. the product of Step B) (0.400 g, 1.38 mmol) in ethanol (16 mL) and water (4 mL) was added iron (power, 0.387 g, 6.94 mmol) and NH.sub.4Cl (0.074 g, 1.38 mmol). The reaction mixture was heated to the reflux temperature at 80? C. for 3 h. After completion of the reaction, the reaction mixture was filtered through Celite? diatomaceous earth filter aid and washed with ethyl acetate (25 mL). The filtrate was evaporated under reduced pressure to give the crude product (0.240 g) as an off-white solid which was used in the next step.
[0632] LCMS (M+1)=259.
Step D: Preparation of N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide
[0633] To a solution of 1-(5-amino-2,4-dimethylphenyl)-3-(2-propyn-1-yloxy)-2-pyrrolidinone (i.e. the product of Step C) (0.210 g, 0.81 mmol) in dichloromethane (10 mL) was added triethylamine (0.2 mL, 1.62 mmol) and Trifluoromethanesulfonic anhydride (Tf.sub.2O) (0.08 mL, 0.48 mmol) at ?78? C. The reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was quenched with water (20 mL) and extracted with dichloromethane (20 mL?2). The organic layer was separated and washed with brine (10 mL) and concentrated under reduced pressure to give the crude compound which was loaded on silica gel column. Elution of the column with 30% ethyl acetate/petroleum ether gave the desired product (80 mg) as an off-white solid.
[0634] .sup.1H NMR (CDCl.sub.3) ? 7.99 (br, 1H), 7.06 (s, 1H), 6.97 (s, 1H), 4.65-4.53 (m, 2H), 4.46-4.42 (t, 1H), 3.70-3.57 (m, 2H), 2.59-2.56 (m, 1H), 2.50-2.49 (t, 1H), 2.26-2.24 (m, 1H), 2.21 (s, 3H), 2.16 (s, 3H).
Synthesis Example 3
Preparation of N-[5-[3-(cyclopropoxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (also known as N-[5-[3-(cyclopropoxy)-2-oxo-pyrrolidin-1-yl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (Compound 3)
Step A: Preparation of tert-butyl 3-(cyclopropoxy)-2-oxo-pyrrolidine-1-carboxylate
[0635] To a solution of tert-butyl 3-diazo-2-oxopyrolidine-1-carboxylate (2 g, 9.47 mmol) and cyclopropanol (0.82 g, 14.21 mmol) in dichloromethane (20 mL) was added dirhodium tetraacetate (41 mg, 0.01 mmol). The mixture was stirred at room temperature for 1 h. Analysis by thin layer chromatography (50% ethyl acetate/petroleum ether) showed completion of the reaction. The reaction mixture was filtered through Celite? diatomaceous earth filter aid; and the filtrate was evaporated under reduced pressure to obtain the crude product. The crude product was loaded on a silica gel column. Elution of the column with 30% ethyl acetate/petroleum ether gave the pure desired product (0.680 g) as off-white solid.
[0636] .sup.1H NMR (CDCl.sub.3) ? 4.17-4.13 (t, 1H), 3.82-3.77 (m, 2H), 3.57-3.52 (m, 1H), 2.28-2.27 (m, 1H), 1.96-1.91 (m, 1H), 1.53 (s, 9H), 0.72-0.49 (m, 4H).
Step B: Preparation of 3-(cyclopropoxy)pyrrolidin-2-one
[0637] To a solution of tert-butyl 3-(cyclopropoxy)-2-oxo-pyrrolidine-1-carboxylate (i.e. the product of Step A) (0.680 g, 2.61 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (0.89 g, 7.84 mmol) dropwise. The reaction mixture was stirred at room temperature for 4 h. Analysis by thin layer chromatography (45% ethyl acetate/petrolium ether ether showed completion of the reaction. The reaction mixture was evaporated under reduced pressure to obtain the crude product. The crude product was co-distilled with CHCl.sub.3 (10 mL?2) to get 3-(cyclopropoxy)pyrrolidin-2-one (0.6 g) as a clear oil liquid.
[0638] .sup.1H NMR (CDCl.sub.3) ? 7.69 (br, 1H), 4.3-4.26 (m, 1H), 3.71-3.68 (m, 1H), 3.56-3.50 (m, 1H), 3.43-3.37 (m, 1H), 2.52-2.44 (m, 1H), 2.16-2.07 (m, 1H), 0.74-0.54 (m, 4H).
Step C: Preparation of 3-(cyclopropoxy)-1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidin-2-one
[0639] To a solution of 3-(cyclopropoxy)pyrrolidin-2-one (i.e. the product of Step B) (0.6 g, 4.25 mmol) in dioxane in a sealed vessel was added 1-bromo-2,4-dimethyl-5-nitrobezene (2.12 g, 8.5 mmol), K.sub.2CO.sub.3 (2.5 g, 17.02 mmol) and N,N-Dimethylethylenediamine (DMEDA) (0.81 g, 8.5 mmol). The reaction was degassed with N.sub.2 gas for 5 min. Copper(I) iodide (0.875 g, 4.2 mmol) was added to the reaction mixture and the reaction mixture was heated to the reflux temperature at 110? C. for 12 h. The reaction mixture was diluted with ethyl acetate and filtered through a pad of Celite? diatomaceous earth filter aid. The resulting filtrate was concentrated under reduced pressure to afford a residue. The residue was purified by column chromatography (30% ethyl acetate in petroleum ether on silica) to afford the desired product (0.650 g) as a white solid.
[0640] .sup.1H NMR (CDCl.sub.3) ? 7.86 (s, 1H), 7.26 (s, 1H), 4.32-4.28 (t, 1H), 3.82-3.79 (m, 1H), 3.75-3.70 (m, 2H), 2.60 (s, 3H), 2.28 (s, 3H), 2.58-2.53 (m, 1H), 2.23-2.18 (m, 1H), 0.79-0.54 (m, 4H).
Step D: Preparation of 1-(5-amino-2,4-dimethylphenyl)-3-(cyclopropyloxy)-2-pyrrolidinone
[0641] To a solution of 3-(cyclopropoxy)-1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidin-2-one (i.e. the product of Step C) (0.610 g, 2.10 mmol) in ethanol (5 mL) and water (5 mL) was added iron (powder, 0.587 g, 10.55 mmol) and NH.sub.4Cl (0.336 g, 6.310 mmol). The reaction mixture was heated at 80? C. for 2 h. After completion of the reaction, the reaction mixture was filtered through Celite? diatomaceous earth filter aid and washed with ethyl acetate (25 mL). The filtrate was evaporated under reduced pressure to give the crude product which was loaded on silica gel column. Elution of the column with 40% ethyl acetate/petroleum ether gave the desired product (0.49 g) as an off-white solid.
[0642] .sup.1H NMR (CDCl.sub.3) ? 6.93 (s, 1H), 6.46 (s, 1H), 4.29-4.26 (t, 1H), 3.83-3.80 (m, 1H), 3.66-3.55 (m, 2H), 2.49-2.44 (m, 1H), 2.18-2.12 (m, 1H), 2.11 (s, 3H), 2.08 (s, 3H), 0.76-0.52 (m, 4H).
Step E: Preparation of N-[5-[3-(cyclopropoxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (also known as N-[5-[3-(cyclopropoxy)-2-oxo-pyrrolidin-1-yl]-2,4-dimethyl-phenyl]-1,1,1-trifluoro-methanesulfonamide)
[0643] To a solution of 1-(5-amino-2,4-dimethylphenyl)-3-(cyclopropyloxy)-2-pyrrolidinone (i.e. the product of Step D) (350 mg, 1.34 mmol) in dichloromethane (10 mL) was added triethylamine (0.37 mL, 2.26 mmol) and Tf.sub.2O (0.34 mL, 2.01 mmol) at ?20? C. The reaction mixture was stirred at room temperature for 3 h. Analysis by thin layer chromatography (50% ethyl acetate/petroleum ether) showed completion of the reaction. The reaction mixture was quenched with water (50 mL) and extracted with diclhloromethane (50 mL?2). The organic layer was separated, washed with brine (25 mL) and dried over Na.sub.2SO.sub.4. The solvent was evaporated and loaded on silica gel column. Elution of the column with 20% ethyl acetate/petroleum ether gave the desired product (140 mg) as an off-white solid.
[0644] .sup.1H NMR (CDCl.sub.3) ? 8.12 (s, 1H), 7.06 (s, 1H), 6.95 (s, 1H), 4.35-4.31 (t, 1H), 3.89-3.84 (m, 1H), 3.69-3.55 (m, 2H), 2.55-2.48 (m, 1H), 2.22 (s, 3H), 2.17 (s, 3H), 2.17 (m, 1H), 0.81-0.76 (m, 1H), 0.68-0.62 (m, 3H).
Synthesis Example 4
Preparation of 1,1,1-trifluoro-N-[5-[3-(hydroxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide (Compound 10)
Step A: Preparation of 1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidin-2-one
[0645] To a stirred solution of 1-bromo-2,4-dimethyl-5-nitro-benzene (5 g, 21.7 mmol) in 1,4-dioxane (50 mL) was added pyrrolidin-2-one (4.6 g, 54.1 mmol), potassium carbonate (8.9 g, 64.4 mmol), copper(I) iodide (3.9 g, 20.5 mmol) and N,N-dimethylethylenediamine (3.82 g, 43.3 mmol). The mixture was sparged with nitrogen gas for 10 min then stirred at 130? C. for 16 h. The mixture was filtered through a pad of Celite, rinsing with ethyl acetate (50 mL). The filtrate was concentrated under reduced pressure and triturated with n-pentane (25 mL) and diethyl ether (5 mL) to give the title compound as an off white solid (5 g).
[0646] .sup.1H NMR (CDCl.sub.3) ? 7.87 (s, 1H), 7.24 (s, 1H), 3.78-3.75 (m, 2H), 2.61-2.57 (m, 5H), 2.30-2.24 (m, 5H).
Step B: Preparation of 1-(5-amino-2,4-dimethyl-phenyl)pyrrolidin-2-one
[0647] To a stirred solution of 1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidin-2-one (i.e. the product of Step A) (5 g, 21.3 mmol) in ethanol (40 mL) and water (12 mL) was added iron powder (6 g, 107 mmol) followed by ammonium chloride (1.13 g, 21.1 mmol). The mixture was stirred at 80? C. for 3 h then filtered through a pad of Celite? diatomaceous earth filter aid, rinsing with ethyl acetate (25 mL). The filtrate was concentrated under reduced pressure to give the title compound as an off white solid (4 g), which was used without further purification.
[0648] .sup.1H NMR (CDCl.sub.3) ? 6.92 (s, 1H), 6.46 (s, 1H), 3.67-3.64 (m, 2H), 3.53 (br s, 2H), 2.55-2.52 (m, 2H), 2.21-2.15 (m, 2H), 2.11 (s, 3H), 2.08 (s, 3H).
Step C: Preparation of N-[2,4-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoro-methanesulfonamide
[0649] To a stirred solution of 1-(5-amino-2,4-dimethyl-phenyl)pyrrolidin-2-one (i.e. the product of Step B) (4 g, 19.6 mmol) in dichloromethane (40 mL) at ?78? C. was added triethylamine (5.9 mL, 42 mmol) and trifluoromethanesulfonic anhydride (3.2 mL, 19 mmol). After 2 h, water (20 ml) was added and the mixture was extracted with ethyl acetate (200 mL?2). The combined organic layer was washed with brine (50 mL) and concentrated under reduced pressure. Column chromatography on silica gel gave the title compound as an off white solid (3 g).
[0650] .sup.1H NMR (CDCl.sub.3) ? 7.05 (s, 1H), 6.95 (s, 1H), 3.70-3.67 (m, 2H), 2.63-2.60 (m, 2H), 2.27-2.21 (m, 2H), 2.20 (s, 3H), 2.17 (s, 3H).
Step D: Preparation of 1,1,1-trifluoro-N-[5-[3-(hydroxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide
[0651] To a stirred solution of N-[2,4-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoro-methanesulfonamide (i.e. the product of Step C) (3 g, 8.9 mmol) in anhydrous tetrahydrofuran (30 mL) at 0? C. was added sodium bis(trimethylsilyl)amide (30 mL, 30 mmol, 1 M in tetrahydrofuran). The mixture was stirred at 0? C. for 30 min then isopentyl nitrite (2.2 g, 18.8 mmol) was added and the mixture was stirred at 0? C. for 2 h. The mixture was quenched with 1 N hydrochloric acid (30 mL) and extracted with ethyl acetate (100 mL?2). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. Trituration with 10% diethyl ether/pentane gave the title compound as an off white solid (1.6 g).
[0652] .sup.1H NMR (DMSO-d.sub.6) ? 11.95 (s, 1H), 11.52 (br s, 1H), 7.24 (br s, 1H), 7.16 (s, 1H), 3.72 (m, 2H), 2.88 (m, 2H), 2.27 (s, 3H), 2.10 (s, 3H).
Synthesis Example 5
Preparation of N-[5-[3-(Ethoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (Compound 12)
[0653] To a stirred solution of 1,1,1-Trifluoro-N-[5-[3-(hydroxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide (i.e. the product of Step D in Synthesis Example 4) (0.4 g, 1.09 mmol) in tetrahydrofuran (20 mL) was added potassium tert-butoxide (3.8 ml, 3.8 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred for 20 min then bromoethane (0.1 mL, 1.3 mmol) was added. After stirring for 16 h, the mixture was acidified to pH-4 with 1 N hydrochloric acid and extracted with ethyl acetate (50 mL?2). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel gave the title compound as an off white solid (160 mg).
[0654] .sup.1H NMR (DMSO-d.sub.6) ? 11.48 (br s, 1H), 7.26 (s, 1H), 7.19 (s, 1H), 4.24 (q, 2H), 3.73 (m, 2H), 2.90 (m, 2H), 2.28 (s, 3H), 2.11 (s, 3H), 1.27 (t, 3H).
[0655] By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 11 can be prepared. The following abbreviations are used in the Tables which follow: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Pr means isopropyl, Bu means butyl, c-Pr cyclopropyl, c-Bu means cyclobutyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, NHMe means methylamino, CN means cyano, Py means pyridinyl, NC.sub.2 means nitro, TMS means trimethylsilyl, S(O)Me means methylsulfinyl, and S(O).sub.2Me means methylsulfonyl.
TABLE-US-00002 TABLE 1
[0656] This disclosure also includes TABLES 2 through 25 wherein the Header Row Phrase in TABLE 1 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 1.
TABLE-US-00003 TABLE Header Row Phrase 2 R.sup.4 = SO.sub.2CF.sub.3 3 R.sup.4 = is SO.sub.2CH.sub.3 4 R.sup.4 = COMe 5 R.sup.4 = COEt 6 R.sup.4 = CH.sub.2OCO-t-Bu 7 R.sup.4 = CH.sub.2OCO-n-Bu 8 R.sup.4 = CH.sub.2OCO-sec-Bu 9 R.sup.4 = CH.sub.2OCO-i-Bu 10 R.sup.4 = CH.sub.2OCO-c-hexyl 11 R.sup.4 = CH.sub.2OCO-c-pentyl 12 R.sup.4 = CH.sub.2OCO-c-butyl 13 R.sup.4 = CH.sub.2OCO-c-propyl 14 R.sup.4 CH.sub.2OCOMe 15 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 16 R.sup.4 = CH.sub.2OCOPh 17 R.sup.4 = CH.sub.2OCO-n-Pr 18 R.sup.4 = CH.sub.2OCO-i-Pr 19 R.sup.4 = (C?O)SMe 20 R.sup.4 = COOMe 21 R.sup.4 = COOEt 22 R.sup.4 = CO-n-Pr 23 R.sup.4 = CONMe2 24 R.sup.4 = (C?O)N-morpholine 25 R4 = (C?S)N-morpholine
TABLE-US-00004 TABLE 26
[0657] This disclosure also includes TABLES 27 through 50 wherein the Header Row Phrase in TABLE 26 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 26.
TABLE-US-00005 TABLE Header Row Phrase 27 R.sup.4 = SC.sub.2CF.sub.3 28 R.sup.4 = SO.sub.2CH.sub.3 29 R.sup.4 = COMe 30 R.sup.4 = COEt 31 R.sup.4 = CH.sub.2OCO-t-Bu 32 R.sup.4 = CH.sub.2OCO-n-Bu 33 R.sup.4 = CH.sub.2OCO-sec-Bu 34 R.sup.4 = CH.sub.2OCO-i-Bu 35 R.sup.4 = CH.sub.2OCO-c-hexyl 36 R.sup.4 = CH.sub.2OCO-c-pentyl 37 R.sup.4 = CH.sub.2OCO-c-butyl 38 R.sup.4 = CH.sub.2OCO-c-propyl 39 R.sup.4 = CH.sub.2OCOMe 40 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 41 R.sup.4 = CH.sub.2OCOPh 42 R.sup.4 = CH.sub.2OCO-n-Pr 43 R.sup.4 = CH.sub.2OCO-i-Pr 44 R.sup.4 = (C?O)SMe 45 R.sup.4 = COOMe 46 R.sup.4 = COOEt 47 R.sup.4 = CO-n-Pr 48 R.sup.4 = CONMe2 49 R.sup.4 = (C?O)N-morpholine 50 R.sup.4 = (C?S)N-morpholine
TABLE-US-00006 TABLE 51
[0658] This disclosure also includes TABLES 52 through 75 wherein the Header Row Phrase in TABLE 51 (i.e. R.sup.4 is H) is replaced with the Header Row Phrase listed in the respective Table, and the R.sup.10 are as defined in TABLE 51.
TABLE-US-00007 TABLE Header Row Phrase 52 R.sup.4 = SO.sub.2CF.sub.3 53 R.sup.4 is SO.sub.2CH.sub.3 54 R.sup.4 = is COMe 55 R.sup.4 = COEt 56 R.sup.4 = CH.sub.2OCO-t-Bu 57 R.sup.4 = CH.sub.2OCO-n-Bu 58 R.sup.4 = CH.sub.2OCO-sec-Bu 59 R.sup.4 = CH.sub.2OCO-i-Bu 60 R.sup.4 = CH.sub.2OCO-c-hexyl 61 R.sup.4 = CH.sub.2OCO-c-pentyl 62 R.sup.4 = CH.sub.2OCO-c-butyl 63 R.sup.4 = CH.sub.2OCO-c-propyl 64 R.sup.4 = CH.sub.2OCOMe 65 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 66 R.sup.4 = CH.sub.2OCOPh 67 R.sup.4 = CH.sub.2OCO-n-Pr 68 R.sup.4 = CH.sub.2OCO-i-Pr 69 R.sup.4 = (C?O)SMe 70 R.sup.4 = COOMe 71 R.sup.4 = COOEt 72 R.sup.4 = CO-n-Pr 73 R.sup.4 = CONMe2 74 R.sup.4 = (C?O)N-morpholine 75 R.sup.4 = (C?S)N-morpholine
TABLE-US-00008 TABLE 76
[0659] This disclosure also includes TABLES 77 through 100 wherein the Header Row Phrase in TABLE 76 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the R.sup.10 are as defined in TABLE 76.
TABLE-US-00009 TABLE Header Row Phrase 77 R.sup.4 = SO.sub.2CF.sub.3 78 R.sup.4 = SO.sub.2CH.sub.3 79 R.sup.4 = COMe 80 R.sup.4 = COEt 81 R.sup.4 = CH.sub.2OCO-t-Bu 82 R.sup.4 = CH.sub.2OCO-n-Bu 83 R.sup.4 = CH.sub.2OCO-sec-Bu 84 R.sup.4 = CH.sub.2OCO-i-Bu 85 R.sup.4 = CH.sub.2OCO-c-hexyl 86 R.sup.4 = CH.sub.2OCO-c-pentyl 87 R.sup.4 = CH.sub.2OCO-c-butyl 88 R.sup.4 = CH.sub.2OCO-c-propyl 89 R.sup.4 CH.sub.2OCOMe 90 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 91 R.sup.4 = CH.sub.2OCOPh 92 R.sup.4 = CH.sub.2OCO-n-Pr 93 R.sup.4 = CH.sub.2OCO-i-Pr 94 R.sup.4 = (C?O)SMe 95 R.sup.4 = COOMe 96 R.sup.4 = COOEt 97 R.sup.4 = CO-n-Pr 98 R.sup.4 = CONMe2 99 R.sup.4 = (C?O)N-morpholine 100 R.sup.4 = (C?S)N-morpholine
TABLE-US-00010 TABLE 101
[0660] This disclosure also includes TABLES 102 through 125 wherein the Header Row Phrase in TABLE 101 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 101.
TABLE-US-00011 TABLE Header Row Phrase 102 R.sup.4 = SO.sub.2CF.sub.3 103 R.sup.4 = SO.sub.2CH.sub.3 104 R.sup.4 = COMe 105 R.sup.4 = COEt 106 R.sup.4 = CH.sub.2OCO-t-Bu 107 R.sup.4 = CH.sub.2OCO-n-Bu 108 R.sup.4 = CH.sub.2OCO-sec-Bu 109 R.sup.4 = CH.sub.2OCO-i-Bu 110 R.sup.4 = CH.sub.2OCO-c-hexyl 111 R.sup.4 = CH.sub.2OCO-c-pentyl 112 R.sup.4 = CH.sub.2OCO-c-butyl 113 R.sup.4 = CH.sub.2OCO-c-propyl 114 R.sup.4 = CH.sub.2OCOMe 115 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 116 R.sup.4 = CH.sub.2OCOPh 117 R.sup.4 = CH.sub.2OCO-n-Pr 118 R.sup.4 = CH.sub.2OCO-i-Pr 119 R.sup.4 = (C?O)SMe 120 R.sup.4 = COOMe 121 R.sup.4 = COOEt 122 R.sup.4 = CO-n-Pr 123 R.sup.4 = CONMe2 124 R.sup.4 = (C?O)N-morpholine 125 R.sup.4 = (C?S)N-morpholine
TABLE-US-00012 TABLE 126
[0661] This disclosure also includes TABLES 127 through 150 wherein the Header Row Phrase in TABLE 126 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 126.
TABLE-US-00013 TABLE Header Row Phrase 127 R.sup.4 = SO.sub.2CF.sub.3 128 R.sup.4 = SO.sub.2CH.sub.3 129 R.sup.4 = COMe 130 R.sup.4 = COEt 131 R.sup.4 = CH.sub.2OCO-t-Bu 132 R.sup.4 = CH.sub.2OCO-n-Bu 133 R.sup.4 = CH.sub.2OCO-sec-Bu 134 R.sup.4 = CH.sub.2OCO-i-Bu 135 R.sup.4 = CH.sub.2OCO-c-hexyl 136 R.sup.4 = CH.sub.2OCO-c-pentyl 137 R.sup.4 = CH.sub.2OCO-c-butyl 138 R.sup.4 = CH.sub.2OCO-c-propyl 139 R.sup.4 = CH.sub.2OCOMe 140 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 141 R.sup.4 = CH.sub.2OCOPh 142 R.sup.4 = CH.sub.2OCO-n-Pr 143 R.sup.4 = CH.sub.2OCO-i-Pr 144 R.sup.4 = (C?O)SMe 145 R.sup.4 = COOMe 146 R.sup.4 = COOEt 147 R.sup.4 = CO-n-Pr 148 R.sup.4 = CONMe2 149 R.sup.4 = (C?O)N-morpholine 150 R.sup.4 = (C?S)N-morpholine
TABLE-US-00014 TABLE 151
[0662] This disclosure also includes TABLES 152 through 175 wherein the Header Row Phrase in TABLE 151 (i.e. R.sup.4 is H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 151.
TABLE-US-00015 TABLE Header Row Phrase 152 R.sup.4 = SO.sub.2CF.sub.3 153 R.sup.4 = SO.sub.2CH.sub.3 154 R.sup.4 = COMe 155 R.sup.4 = COEt 156 R.sup.4 = CH.sub.2OCO-t-Bu 157 R.sup.4 = CH.sub.2OCO-n-Bu 158 R.sup.4 = CH.sub.2OCO-sec-Bu 159 R.sup.4 = CH.sub.2OCO-i-Bu 160 R.sup.4 = CH.sub.2OCO-c-hexyl 161 R.sup.4 = CH.sub.2OCO-c-pentyl 162 R.sup.4 = CH.sub.2OCO-c-butyl 163 R.sup.4 = CH.sub.2OCO-c-propyl 164 R.sup.4 = CH.sub.2OCOMe 165 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 166 R.sup.4 = CH.sub.2OCOPh 167 R.sup.4 = CH.sub.2OCO-n-Pr 168 R.sup.4 = CH.sub.2OCO-i-Pr 169 R.sup.4 = (C?O)SMe 170 R.sup.4 = COOMe 171 R.sup.4 = COOEt 172 R.sup.4 = CO-n-Pr 173 R.sup.4 = CONMe2 174 R.sup.4 = (C?O)N-morpholine 175 R.sup.4 = (C?S)N-morpholine
TABLE-US-00016 TABLE 176
[0663] This disclosure also includes TABLES 177 through 200 wherein the Header Row Phrase in TABLE 176 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 176.
TABLE-US-00017 TABLE Header Row Phrase 177 R.sup.4 = SO.sub.2CF.sub.3 178 R.sup.4 = SO.sub.2CH.sub.3 179 R.sup.4 = COMe 180 R.sup.4 = COEt 181 R.sup.4 = CH.sub.2OCO-t-Bu 182 R.sup.4 = CH.sub.2OCO-n-Bu 183 R.sup.4 = CH.sub.2OCO-sec-Bu 184 R.sup.4 = CH.sub.2OCO-i-Bu 185 R.sup.4 = CH.sub.2OCO-c-hexyl 186 R.sup.4 = CH.sub.2OCO-c-pentyl 187 R.sup.4 = CH.sub.2OCO-c-butyl 188 R.sup.4 = CH.sub.2OCO-c-propyl 189 R.sup.4 = CH.sub.2OCOMe 190 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 191 R.sup.4 = CH.sub.2OCOPh 192 R.sup.4 = CH.sub.2OCO-n-Pr 193 R.sup.4 = CH.sub.2OCO-i-Pr 194 R.sup.4 = (C?O)SMe 195 R.sup.4 = COOMe 196 R.sup.4 = COOEt 197 R.sup.4 = CO-n-Pr 198 R.sup.4 = CONMe2 199 R.sup.4 = (C?O)N-morpholine 200 R.sup.4 = (C?S)N-morpholine
TABLE-US-00018 TABLE 201
[0664] This disclosure also includes TABLES 202 through 225 wherein the Header Row Phrase in TABLE 201 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 201.
TABLE-US-00019 TABLE Header Row Phrase 202 R.sup.4 = SO.sub.2CF.sub.3 203 R.sup.4 = SO.sub.2CH.sub.3 204 R.sup.4 = COMe 205 R.sup.4 = COEt 206 R.sup.4 = CH.sub.2OCO-t-Bu 207 R.sup.4 = CH.sub.2OCO-n-Bu 208 R.sup.4 = CH.sub.2OCO-sec-Bu 209 R.sup.4 = CH.sub.2OCO-i-Bu 210 R.sup.4 = CH.sub.2OCO-c-hexyl 211 R.sup.4 = CH.sub.2OCO-c-pentyl 212 R.sup.4 = CH.sub.2OCO-c-butyl 213 R.sup.4 = CH.sub.2OCO-c-propyl 214 R.sup.4 = CH.sub.2OCOMe 215 R.sup.4 = CH.sub.2OCOCH.sub.2CH.sub.3 216 R.sup.4 = CH.sub.2OCOPh 217 R.sup.4 = CH.sub.2OCO-n-Pr 218 R.sup.4 = CH.sub.2OCO-i-Pr 219 R.sup.4 = (C?O)SMe 220 R.sup.4 = COOMe 221 R.sup.4 = COOEt 222 R.sup.4 = CO-n-Pr 223 R.sup.4 = CONMe2 224 R.sup.4 = (C?O)N-morpholine 225 R.sup.4 = (C?S)N-morpholine
TABLE-US-00020 TABLE 226
[0665] This disclosure also includes TABLES 227 through 250 wherein the Header Row Phrase in TABLE 226 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 226.
TABLE-US-00021 TABLE Header Row Phrase 227 R.sup.4 = SO.sub.2CF.sub.3 228 R.sup.4 = SO.sub.2CH.sub.3 229 R.sup.4 = COMe 230 R.sup.4 = COEt 231 R.sup.4 = CH.sub.2OCO-t-Bu 232 R.sup.4 = CH.sub.2OCO-n-Bu 233 R.sup.4 = CH.sub.2OCO-sec-Bu 234 R.sup.4 = CH.sub.2OCO-i-Bu 235 R.sup.4 = CH.sub.2OCO-c-hexyl 236 R.sup.4 = CH.sub.2OCO-c-pentyl 237 R.sup.4 = CH.sub.2OCO-c-butyl 238 R.sup.4 = CH.sub.2OCO-c-propyl 239 R.sup.4 CH.sub.2OCOMe 240 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 241 R.sup.4 = CH.sub.2OCOPh 242 R.sup.4 = CH.sub.2OCO-n-Pr 243 R.sup.4 = CH.sub.2OCO-i-Pr 244 R.sup.4 = (C?O)SMe 245 R.sup.4 = COOMe 246 R.sup.4 = COOEt 247 R.sup.4 = CO-n-Pr 248 R.sup.4 = CONMe2 249 R.sup.4 = (C?O)N-morpholine 250 R.sup.4 = (C?S)N-morpholine
TABLE-US-00022 TABLE 251
[0666] This disclosure also includes TABLES 252 through 275 wherein the Header Row Phrase in TABLE 251 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 251.
TABLE-US-00023 TABLE Header Row Phrase 252 R.sup.4 = SO.sub.2CF.sub.3 253 R.sup.4 = SO.sub.2CH.sub.3 254 R.sup.4 = COMe 255 R.sup.4 = COEt 256 R.sup.4 = CH.sub.2OCO-t-Bu 257 R.sup.4 = CH.sub.2OCO-n-Bu 258 R.sup.4 = CH.sub.2OCO-sec-Bu 259 R.sup.4 = CH.sub.2OCO-i-Bu 260 R.sup.4 = CH.sub.2OCO-c-hexyl 261 R.sup.4 = CH.sub.2OCO-c-pentyl 262 R.sup.4 = CH.sub.2OCO-c-butyl 263 R.sup.4 = CH.sub.2OCO-c-propyl 264 R.sup.4 CH.sub.2OCOMe 265 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 266 R.sup.4 = CH.sub.2OCOPh 267 R.sup.4 = CH.sub.2OCO-n-Pr 268 R.sup.4 = CH.sub.2OCO-i-Pr 269 R.sup.4 = (C?O)SMe 270 R.sup.4 = COOMe 271 R.sup.4 = COOEt 272 R.sup.4 = CO-n-Pr 273 R.sup.4 = CONMe2 274 R.sup.4 = (C?O)N-morpholine 275 R.sup.4 = (C?S)N-morpholine
TABLE-US-00024 TABLE 276
[0667] This disclosure also includes TABLES 277 through 300 wherein the Header Row Phrase in TABLE 276 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 276.
TABLE-US-00025 TABLE Header Row Phrase 277 R.sup.4 = SO.sub.2CF.sub.3 278 R.sup.4 = SO.sub.2CH.sub.3 279 R.sup.4 = COMe 280 R.sup.4 = COEt 281 R.sup.4 = CH.sub.2OCO-t-Bu 282 R.sup.4 = CH.sub.2OCO-n-Bu 283 R.sup.4 = CH.sub.2OCO-sec-Bu 284 R.sup.4 = CH.sub.2OCO-i-Bu 285 R.sup.4 = CH.sub.2OCO-c-hexyl 286 R.sup.4 = CH.sub.2OCO-c-pentyl 287 R.sup.4 = CH.sub.2OCO-c-butyl 288 R.sup.4 = CHOCO-c-propyl 289 R.sup.4 CHOCOMe 290 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 291 R.sup.4 = CH.sub.2OCOPh 292 R.sup.4 = CH.sub.2OCO-n-Pr 293 R.sup.4 = CH.sub.2OCO-i-Pr 294 R.sup.4 = (C?O)SMe 295 R.sup.4 = COOMe 296 R.sup.4 = COOEt 297 R.sup.4 = CO-n-Pr 298 R.sup.4 = CONMe2 299 R.sup.4 = (C?O)N-morpholine 300 R.sup.4 = (C?S)N-morpholine
TABLE-US-00026 TABLE 301
[0668] This disclosure also includes TABLES 302 through 325 wherein the Header Row Phrase in TABLE 301 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 301.
TABLE-US-00027 TABLE Header Row Phrase 302 R.sup.4 = SO.sub.2CF.sub.3 303 R.sup.4 = SO.sub.2CH.sub.3 304 R.sup.4 = COMe 305 R.sup.4 = COEt 306 R.sup.4 = CH.sub.2OCO-t-Bu 307 R.sup.4 = CH.sub.2OCO-n-Bu 308 R.sup.4 = CH.sub.2OCO-sec-Bu 309 R.sup.4 = CH.sub.2OCO-i-Bu 310 R.sup.4 = CH.sub.2OCO-c-hexyl 311 R.sup.4 = CH.sub.2OCO-c-pentyl 312 R.sup.4 = CH.sub.2OCO-c-butyl 313 R.sup.4 = CH.sub.2OCO-c-propyl 314 R.sup.4 CH.sub.2OCOMe 315 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 316 R.sup.4 = CH.sub.2OCOPh 317 R.sup.4 = CH.sub.2OCO-n-Pr 318 R.sup.4 = CH.sub.2OCO-i-Pr 319 R.sup.4 = (C?O)SMe 320 R.sup.4 = COOMe 321 R.sup.4 = COOEt 322 R.sup.4 = CO-n-Pr 323 R.sup.4 = CONMe.sup.2 324 R.sup.4 = (C?O)N-morpholine 325 R.sup.4 = (C?S)N-morpholine
TABLE-US-00028 TABLE 326
[0669] This disclosure also includes TABLES 327 through 350 wherein the Header Row Phrase in TABLE 326 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 326.
TABLE-US-00029 TABLE Header Row Phrase 327 R.sup.4 = SO.sub.2CF.sub.3 328 R.sup.4 = SO.sub.2CH.sub.3 329 R.sup.4 = COMe 330 R.sup.4 = COEt 331 R.sup.4 = CH.sub.2OCO-t-Bu 332 R.sup.4 = CH.sub.2OCO-n-Bu 333 R.sup.4 = CH.sub.2OCO-sec-Bu 334 R.sup.4 = CH.sub.2OCO-i-Bu 335 R.sup.4 = CH.sub.2OCO-c-hexyl 336 R.sup.4 = CH.sub.2OCO-c-pentyl 337 R.sup.4 = CH.sub.2OCO-c-butyl 338 R.sup.4 = CH.sub.2OCO-c-propyl 339 R.sup.4 CH.sub.2OCOMe 340 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 341 R.sup.4 = CH.sub.2OCOPh 342 R.sup.4 = CH.sub.2OCO-n-Pr 343 R.sup.4 = CH.sub.2OCO-i-Pr 344 R.sup.4 = (C?O)SMe 345 R.sup.4 = COOMe 346 R.sup.4 = COOEt 347 R.sup.4 = CO-n-Pr 348 R.sup.4 = CONMe2 349 R.sup.4 = (C?O)N-morpholine 350 R.sup.4 = (C?S)N-morpholine
TABLE-US-00030 TABLE 351
[0670] This disclosure also includes TABLES 352 through 375 wherein the Header Row Phrase in TABLE 351 (i.e. R.sup.4?H) is replaced with the Header Row Phrase listed in the respective TABLE, and the remaining variable(s) are as defined in TABLE 351.
TABLE-US-00031 TABLE Header Row Phrase 352 R.sup.4 = SO.sub.2CF.sub.3 353 R.sup.4 = SO.sub.2CH.sub.3 354 R.sup.4 = COMe 355 R.sup.4 = COEt 356 R.sup.4 = CH.sub.2OCO-t-Bu 357 R.sup.4 = CH.sub.2OCO-n-Bu 358 R.sup.4 = CH.sub.2OCO-sec-Bu 359 R.sup.4 = CH.sub.2OCO-i-Bu 360 R.sup.4 = CH.sub.2OCO-c-hexyl 361 R.sup.4 = CH.sub.2OCO-c-pentyl 362 R.sup.4 = CH.sub.2OCO-c-butyl 363 R.sup.4 = CH.sub.2OCO-c-propyl 364 R.sup.4 CH.sub.2OCOMe 365 R.sup.4 CH.sub.2OCOCH.sub.2CH.sub.3 366 R.sup.4 = CH.sub.2OCOPh 367 R.sup.4 = CH.sub.2OCO-n-Pr 368 R.sup.4 = CH.sub.2OCO-i-Pr 369 R.sup.4 = (C?O)SMe 370 R.sup.4 = COOMe 371 R.sup.4 = COOEt 372 R.sup.4 = CO-n-Pr 373 R.sup.4 = CONMe2 374 R.sup.4 = (C?O)N-morpholine 375 R.sup.4 = (C?S)N-morpholine
Formulation/Utility
[0671] A compound of this disclosure will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
[0672] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
[0673] The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (wettable) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or overcoated). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
[0674] Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
[0675] The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
Weight Percent
[0676]
TABLE-US-00032 Active Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and Powders Oil Dispersions, Suspensions, 1-50 40-99 0-50 Emulsions, Solutions (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions 90-99 0-10 0-2
[0677] Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
[0678] Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and ?-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C.sub.6-C.sub.22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
[0679] The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as surface-active agents) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
[0680] Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.
[0681] Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.
[0682] Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quatemary salts and diquatemary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
[0683] Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
[0684] Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
[0685] The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 ?m can be wet milled using media mills to obtain particles with average diameters below 3 ?m. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 ?m range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, Agglomeration, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.
[0686] For further information regarding the art of formulation, see T. S. Woods, The Formulator's ToolboxProduct Forms for Modern Agriculture in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, U K, 2000.
[0687] In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.
Example A
High Strength Concentrate
[0688]
TABLE-US-00033 Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%
Example B
Wettable Powder
[0689]
TABLE-US-00034 Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%
Example C
Granule
[0690]
TABLE-US-00035 Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)
Example D
Extruded Pellet
[0691]
TABLE-US-00036 Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%
Example E
Emulsifiable Concentrate
[0692]
TABLE-US-00037 Compound 1 10.0% polyoxyethylene sorbitol hexoleate 20.0% C.sub.6-C.sub.10 fatty acid methyl ester 70.0%
Example F
Microemulsion
[0693]
TABLE-US-00038 Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water 20.0%
Example G
Suspension Concentrate
[0694]
TABLE-US-00039 Compound 1 35% butyl polyoxyethylene/polypropylene block copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% water 53.7%
Example H
Emulsion in Water
[0695]
TABLE-US-00040 Compound 1 10.0% butyl polyoxyethylene/polypropylene block copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0 water 58.7%
Example I
Oil Dispersion
[0696]
TABLE-US-00041 Compound 1 25% polyoxyethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5%.sup.
[0697] Additional Example Formulations include Examples A through I above wherein Compound 1 is replaced in each of the Examples A through I with the respective compounds from Index Table A as shown below.
TABLE-US-00042 Compound No. Compound No. Compound No. Compound No. Compound No. Compound 2 Compound 4 Compound 10 Compound 11 Compound 18 Compound 3 Compound 5 Compound 12 Compound 13 Compound 19 Compound 6 Compound 7 Compound 14 Compound 15 Compound 20 Compound 8 Compound 9 Compound 16 Compound 17 Compound 21 Compound No. Compound No. Compound No. Compound No. Compound No. Compound 22 Compound 24 Compound 30 Compound 31 Compound 38 Compound 23 Compound 25 Compound 32 Compound 33 Compound 39 Compound 26 Compound 27 Compound 34 Compound 35 Compound 40 Compound 28 Compound 29 Compound 36 Compound 37 Compound 41 Compound 42 Compound 44 Compound 46 Compound 47 Compound 50 Compound 43 Compound 45 Compound 48 Compound 49 Compound 51 Compound 52 Compound 53 Compound 54 Compound 55 Compound 56 Compound 57 Compound 58 Compound 59 Compound 60 Compound 61 Compound 62 Compound 63 Compound 64
[0698] Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. The compounds of the disclosure generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds or by selective activity at the locus of physiological inhibition in crops and weeds or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.
[0699] As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the disclosure or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation. Undesired vegetation includes at least one selected from the group consisting of grass weeds and broadleaf weeds. Undesired vegetation is selected from the group consisting of annual bluegrass, Benghal dayflower, blackgrass, black nightshade, broadleaf signalgrass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, corn poppies, field violet, giant foxtail, goosegrass, green foxtail, guinea grass, hairy beggarticks, herbicide-resistant black grass, horseweed, Italian rye grass, jimsonweed, Johnson grass (Sorghum halepense), large crabgrass, little seed canary grass, morning glory, Pennsylvania smartweed, pitted morning glory, prickly sida, quackgrass, redroot pigweed, shattercane, shepherd's purse, silky windgrass, sunflower (as weed in potato), wild buckwheat (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild pointsettia, yellow foxtail, and yellow nutsedge (Cyperus esculentus).
[0700] A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
[0701] In one common embodiment, a compound of the disclosure is applied, typically in a formulated composition, to a locus comprising desired vegetation (e.g., crops) and undesired vegetation (i.e. weeds), both of which may be seeds, seedlings and/or larger plants, in contact with a growth medium (e.g., soil). In this locus, a composition comprising a compound of the disclosure can be directly applied to a plant or a part thereof, particularly of the undesired vegetation, and/or to the growth medium in contact with the plant.
[0702] Plant varieties and cultivars of the desired vegetation in the locus treated with a compound of the disclosure can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
[0703] Genetically modified plant cultivars in the locus which can be treated according to the invention include those that are resistant against one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperature, soil salinity, etc.) or that contain other desirable characteristics. Plants can be genetically modified to exhibit traits of, for example, herbicide tolerance, insect-resistance, modified oil profiles or drought tolerance.
[0704] Although most typically, compounds of the invention are used to control undesired vegetation, contact of desired vegetation in the treated locus with compounds of the invention may result in super-additive or synergistic effects with genetic traits in the desired vegetation, including traits incorporated through genetic modification. For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic/abiotic stresses or storage stability may be greater than expected from the genetic traits in the desired vegetation.
[0705] Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
[0706] A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bixlozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, epyrifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon orbencarb or thosulfamuron oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
[0707] Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A.sub.4 and A.sub.7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
[0708] General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Famham, Surrey, U. K., 2001.
[0709] For embodiments where one or more of these various mixing partners are used, the mixing partners are typically used in the amounts similar to amounts customary when the mixture partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between one-half and the full application rate specified on product labels for use of active ingredient alone. These amounts are listed in references such as The Pesticide Manual and The BioPesticide Manual. The weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.
[0710] In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
[0711] Of note is a combination of a compound of the disclosure with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
[0712] Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and 3-oxo-1-cyclohexen-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
[0713] Compounds of the invention cans also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect.
[0714] Of note is a composition comprising a compound of the disclosure (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
[0715] Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of atrazine, azimsulfuron, beflubutamid, S-beflubutamid, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (CA No. 81777-95-9) and 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (CA No. 81778-66-7) ethametsulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, pethoxamid, picloram, pyroxasulfone, quinclorac, rimsulfuron, rinskor, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl and tribenuron-methyl.
[0716] Table A1 lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound # in the Component (a) column is identified in Index Table A. The second column of Table A1 lists the specific Component (b) compound (e.g., 2,4-D in the first line). The third, fourth and fifth columns of Table A1 lists ranges of weight ratios for rates at which the Component (a) compound is typically applied to a field-grown crop relative to Component (b) (i.e. (a):(b)). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) (i.e. Compound 45 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1:192-6:1. The remaining lines of Table A1 are to be construed similarly.
TABLE-US-00043 TABLE A1 Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio 1 2,4-D 1:192-6:1 1:64-2:1 1:24-1:3 1 Acetochlor 1:768-2:1 1:256-1:2 1:96-1:11 1 Acifluorfen 1:96-12:1 1:32-4:1 1:12-1:2 1 Aclonifen 1:857-2:1 1:285-1:3 1:107-1:12 1 Alachlor 1:768-2:1 1:256-1:2 1:96-1:11 1 Ametryn 1:384-3:1 1:128-1:1 1:48-1:6 1 Amicarbazone 1:192-6:1 1:64-2:1 1:24-1:3 1 Amidosulfuron 1:6-168:1 1:2-56:1 1:1-11:1 1 Aminocyclopyrachlor 1:48-24:1 1:16-8:1 1:6-2:1 1 Aminopyralid 1:20-56:1 1:6-19:1 1:2-4:1 1 Amitrole 1:768-2:1 1:256-1:2 1:96-1:11 1 Anilofos 1:96-12:1 1:32-4:1 1:12-1:2 1 Asulam 1:960-2:1 1:320-1:3 1:120-1:14 1 Atrazine 1:192-6:1 1:64-2:1 1:24-1:3 1 Azimsulfuron 1:6-168:1 1:2-56:1 1:1-11:1 1 Beflubutamid 1:342-4:1 1:114-2:1 1:42-1:5 1 Benfuresate 1:617-2:1 1:205-1:2 1:77-1:9 1 Bensulfuron-methyl 1:25-45:1 1:8-15:1 1:3-3:1 1 Bentazone 1:192-6:1 1:64-2:1 1:24-1:3 1 Benzobicyclon 1:85-14:1 1:28-5:1 1:10-1:2 1 Benzofenap 1:257-5:1 1:85-2:1 1:32-1:4 1 Bicyclopyrone 1:42-27:1 1:14-9:1 1:5-2:1 1 Bifenox 1:257-5:1 1:85-2:1 1:32-1:4 1 Bispyribac-sodium 1:10-112:1 1:3-38:1 1:1-7:1 1 Bromacil 1:384-3:1 1:128-1:1 1:48-1:6 1 Bromobutide 1:384-3:1 1:128-1:1 1:48-1:6 1 Bromoxynil 1:96-12:1 1:32-4:1 1:12-1:2 1 Butachlor 1:768-2:1 1:256-1:2 1:96-1:11 1 Butafenacil 1:42-27:1 1:14-9:1 1:5-2:1 1 Butylate 1:1542-1:2 1:514-1:5 1:192-1:22 1 Carfenstrole 1:192-6:1 1:64-2:1 1:24-1:3 1 Carfentrazone-ethyl 1:128-9:1 1:42-3:1 1:16-1:2 1 Chlorimuron-ethyl 1:8-135:1 1:2-45:1 1:1-9:1 1 Chlorotoluron 1:768-2:1 1:256-1:2 1:96-1:11 1 Chlorsulfuron 1:6-168:1 1:2-56:1 1:1-11:1 1 Cincosulfuron 1:17-68:1 1:5-23:1 1:2-5:1 1 Cinidon-ethyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Cinmethylin 1:34-34:1 1:11-12:1 1:4-3:1 1 Clacyfos 1:34-34:1 1:11-12:1 1:4-3:1 1 Clethodim 1:48-24:1 1:16-8:1 1:6-2:1 1 Clodinafop-propargyl 1:20-56:1 1:6-19:1 1:2-4:1 1 Clomazone 1:384-3:1 1:128-1:1 1:48-1:6 1 Clomeprop 1:171-7:1 1:57-3:1 1:21-1:3 1 Clopyralid 1:192-6:1 1:64-2:1 1:24-1:3 1 Cloransulam-methyl 1:12-96:1 1:4-32:1 1:1-6:1 1 Cumyluron 1:384-3:1 1:128-1:1 1:48-1:6 1 Cyanazine 1:384-3:1 1:128-1:1 1:48-1:6 1 Cyclopyrimorate 1:17-68:1 1:5-23:1 1:2-5:1 1 Cyclosulfamuron 1:17-68:1 1:5-23:1 1:2-5:1 1 Cycloxydim 1:96-12:1 1:32-4:1 1:12-1:2 1 Cyhalofop 1:25-45:1 1:8-15:1 1:3-3:1 1 Daimuron 1:192-6:1 1:64-2:1 1:24-1:3 1 Desmedipham 1:322-4:1 1:107-2:1 1:40-1:5 1 Dicamba 1:192-6:1 1:64-2:1 1:24-1:3 1 Dichlobenil 1:1371-1:2 1:457-1:4 1:171-1:20 1 Dichlorprop 1:925-2:1 1:308-1:3 1:115-1:13 1 Diclofop-methyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Diclosulam 1:10-112:1 1:3-38:1 1:1-7:1 1 Difenzoquat 1:288-4:1 1:96-2:1 1:36-1:4 1 Diflufenican 1:857-2:1 1:285-1:3 1:107-1:12 1 Diflufenzopyr 1:12-96:1 1:4-32:1 1:1-6:1 1 Dimethachlor 1:768-2:1 1:256-1:2 1:96-1:11 1 Dimethametryn 1:192-6:1 1:64-2:1 1:24-1:3 1 Dimethenamid-P 1:384-3:1 1:128-1:1 1:48-1:6 1 Dithiopyr 1:192-6:1 1:64-2:1 1:24-1:3 1 Diuron 1:384-3:1 1:128-1:1 1:48-1:6 1 EPTC 1:768-2:1 1:256-1:2 1:96-1:11 1 Esprocarb 1:1371-1:2 1:457-1:4 1:171-1:20 1 Ethalfluralin 1:384-3:1 1:128-1:1 1:48-1:6 1 Ethametsulfuron-methyl 1:17-68:1 1:5-23:1 1:2-5:1 1 Ethoxyfen 1:8-135:1 1:2-45:1 1:1-9:1 1 Ethoxysulfuron 1:20-56:1 1:6-19:1 1:2-4:1 1 Etobenzanid 1:257-5:1 1:85-2:1 1:32-1:4 1 Fenoxaprop-ethyl 1:120-10:1 1:40-4:1 1:15-1:2 1 Fenoxasulfone 1:85-14:1 1:28-5:1 1:10-1:2 1 Fenquinotrione 1:17-68:1 1:5-23:1 1:2-5:1 1 Fentrazamide 1:17-68:1 1:5-23:1 1:2-5:1 1 Flazasulfuron 1:17-68:1 1:5-23:1 1:2-5:1 1 Florasulam 1:2-420:1 1:1-140:1 2:1-27:1 1 Fluazifop-butyl 1:192-6:1 1:64-2:1 1:24-1:3 1 Flucarbazone 1:8-135:1 1:2-45:1 1:1-9:1 1 Flucetosulfuron 1:8-135:1 1:2-45:1 1:1-9:1 1 Flufenacet 1:257-5:1 1:85-2:1 1:32-1:4 1 Flumetsulam 1:24-48:1 1:8-16:1 1:3-3:1 1 Flumiclorac-pentyl 1:10-112:1 1:3-38:1 1:1-7:1 1 Flumioxazin 1:25-45:1 1:8-15:1 1:3-3:1 1 Fluometuron 1:384-3:1 1:128-1:1 1:48-1:6 1 Flupyrsulfuron-methyl 1:3-336:1 1:1-112:1 2:1-21:1 1 Fluridone 1:384-3:1 1:128-1:1 1:48-1:6 1 Fluroxypyr 1:96-12:1 1:32-4:1 1:12-1:2 1 Flurtamone 1:857-2:1 1:285-1:3 1:107-1:12 1 Fluthiacet-methyl 1:48-42:1 1:16-14:1 1:3-3:1 1 Fomesafen 1:96-12:1 1:32-4:1 1:12-1:2 1 Foramsulfuron 1:13-84:1 1:4-28:1 1:1-6:1 1 Glufosinate 1:288-4:1 1:96-2:1 1:36-1:4 1 Glyphosate 1:288-4:1 1:96-2:1 1:36-1:4 1 Halosulfuron-methyl 1:17-68:1 1:5-23:1 1:2-5:1 1 Halauxifen 1:20-56:1 1:6-19:1 1:2-4:1 1 Halauxifen methyl 1:20-56:1 1:6-19:1 1:2-4:1 1 Haloxyfop-methyl 1:34-34:1 1:11-12:1 1:4-3:1 1 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:3 1 Hydantocidin 1:1100-16:1 1:385-8:1 1:144-4:1 1 Imazamox 1:13-84:1 1:4-28:1 1:1-6:1 1 Imazapic 1:20-56:1 1:6-19:1 1:2-4:1 1 Imazapyr 1:85-14:1 1:28-5:1 1:10-1:2 1 Imazaquin 1:34-34:1 1:11-12:1 1:4-3:1 1 Imazethabenz-methyl 1:171-7:1 1:57-3:1 1:21-1:3 1 Imazethapyr 1:24-48:1 1:8-16:1 1:3-3:1 1 Imazosulfuron 1:27-42:1 1:9-14:1 1:3-3:1 1 Indanofan 1:342-4:1 1:114-2:1 1:42-1:5 1 Indaziflam 1:25-45:1 1:8-15:1 1:3-3:1 1 Iodosulfuron-methyl 1:3-336:1 1:1-112:1 2:1-21:1 1 Ioxynil 1:192-6:1 1:64-2:1 1:24-1:3 1 Ipfencarbazone 1:85-14:1 1:28-5:1 1:10-1:2 1 Isoproturon 1:384-3:1 1:128-1:1 1:48-1:6 1 Isoxaben 1:288-4:1 1:96-2:1 1:36-1:4 1 Isoxaflutole 1:60-20:1 1:20-7:1 1:7-2:1 1 Lactofen 1:42-27:1 1:14-9:1 1:5-2:1 1 Lenacil 1:384-3:1 1:128-1:1 1:48-1:6 1 Linuron 1:384-3:1 1:128-1:1 1:48-1:6 1 MCPA 1:192-6:1 1:64-2:1 1:24-1:3 1 MCPB 1:288-4:1 1:96-2:1 1:36-1:4 1 Mecoprop 1:768-2:1 1:256-1:2 1:96-1:11 1 Mefenacet 1:384-3:1 1:128-1:1 1:48-1:6 1 Mefluidide 1:192-6:1 1:64-2:1 1:24-1:3 1 Mesosulfuron-methyl 1:5-224:1 1:1-75:1 1:1-14:1 1 Mesotrione 1:42-27:1 1:14-9:1 1:5-2:1 1 Metamifop 1:42-27:1 1:14-9:1 1:5-2:1 1 Metazachlor 1:384-3:1 1:128-1:1 1:48-1:6 1 Metazosulfuron 1:25-45:1 1:8-15:1 1:3-3:1 1 Methabenzthiazuron 1:768-2:1 1:256-1:2 1:96-1:11 1 Metolachlor 1:768-2:1 1:256-1:2 1:96-1:11 1 Metosulam 1:8-135:1 1:2-45:1 1:1-9:1 1 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3 1 Metsulfuron-methyl 1:2-560:1 1:1-187:1 3:1-35:1 1 Molinate 1:1028-2:1 1:342-1:3 1:128-1:15 1 Napropamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3 1 Naptalam 1:192-6:1 1:64-2:1 1:24-1:3 1 Nicosulfuron 1:12-96:1 1:4-32:1 1:1-6:1 1 Norflurazon 1:1152-1:1 1:384-1:3 1:144-1:16 1 Orbencarb 1:1371-1:2 1:457-1:4 1:171-1:20 1 Orthosulfamuron 1:20-56:1 1:6-19:1 1:2-4:1 1 Oryzalin 1:514-3:1 1:171-1:2 1:64-1:8 1 Oxadiargyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Oxadiazon 1:548-3:1 1:182-1:2 1:68-1:8 1 Oxasulfuron 1:27-42:1 1:9-14:1 1:3-3:1 1 Oxaziclomefone 1:42-27:1 1:14-9:1 1:5-2:1 1 Oxyfluorfen 1:384-3:1 1:128-1:1 1:48-1:6 1 Paraquat 1:192-6:1 1:64-2:1 1:24-1:3 1 Pendimethalin 1:384-3:1 1:128-1:1 1:48-1:6 1 Penoxsulam 1:10-112:1 1:3-38:1 1:1-7:1 1 Penthoxamid 1:384-3:1 1:128-1:1 1:48-1:6 1 Pentoxazone 1:102-12:1 1:34-4:1 1:12-1:2 1 Phenmedipham 1:102-12:1 1:34-4:1 1:12-1:2 1 Picloram 1:96-12:1 1:32-4:1 1:12-1:2 1 Picolinafen 1:34-34:1 1:11-12:1 1:4-3:1 1 Pinoxaden 1:25-45:1 1:8-15:1 1:3-3:1 1 Pretilachlor 1:192-6:1 1:64-2:1 1:24-1:3 1 Primisulfuron-methyl 1:8-135:1 1:2-45:1 1:1-9:1 1 Prodiamine 1:384-3:1 1:128-1:1 1:48-1:6 1 Profoxydim 1:42-27:1 1:14-9:1 1:5-2:1 1 Prometryn 1:384-3:1 1:128-1:1 1:48-1:6 1 Propachlor 1:1152-1:1 1:384-1:3 1:144-1:16 1 Propanil 1:384-3:1 1:128-1:1 1:48-1:6 1 Propaquizafop 1:48-24:1 1:16-8:1 1:6-2:1 1 Propoxycarbazone 1:17-68:1 1:5-23:1 1:2-5:1 1 Propyrisulfuron 1:17-68:1 1:5-23:1 1:2-5:1 1 Propyzamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Prosulfocarb 1:1200-1:2 1:400-1:4 1:150-1:17 1 Prosulfuron 1:6-168:1 1:2-56:1 1:1-11:1 1 Pyraclonil 1:42-27:1 1:14-9:1 1:5-2:1 1 Pyraflufen-ethyl 1:5-224:1 1:1-75:1 1:1-14:1 1 Pyrasulfotole 1:13-84:1 1:4-28:1 1:1-6:1 1 Pyrazolynate 1:857-2:1 1:285-1:3 1:107-1:12 1 Pyrazosulfuron-ethyl 1:10-112:1 1:3-38:1 1:1-7:1 1 Pyrazoxyfen 1:5-224:1 1:1-75:1 1:1-14:1 1 Pyribenzoxim 1:10-112:1 1:3-38:1 1:1-7:1 1 Pyributicarb 1:384-3:1 1:128-1:1 1:48-1:6 1 Pyridate 1:288-4:1 1:96-2:1 1:36-1:4 1 Pyriftalid 1:10-112:1 1:3-38:1 1:1-7:1 1 Pyriminobac-methyl 1:20-56:1 1:6-19:1 1:2-4:1 1 Pyrimisulfan 1:17-68:1 1:5-23:1 1:2-5:1 1 Pyrithiobac 1:24-48:1 1:8-16:1 1:3-3:1 1 Pyroxasulfone 1:85-14:1 1:28-5:1 1:10-1:2 1 Pyroxsulam 1:5-224:1 1:1-75:1 1:1-14:1 1 Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3 1 Quizalofop-ethyl 1:42-27:1 1:14-9:1 1:5-2:1 1 Rimsulfuron 1:13-84:1 1:4-28:1 1:1-6:1 1 Saflufenacil 1:25-45:1 1:8-15:1 1:3-3:1 1 Sethoxydim 1:96-12:1 1:32-4:1 1:12-1:2 1 Simazine 1:384-3:1 1:128-1:1 1:48-1:6 1 Sulcotrione 1:120-10:1 1:40-4:1 1:15-1:2 1 Sulfentrazone 1:147-8:1 1:49-3:1 1:18-1:3 1 Sulfometuron-methyl 1:34-34:1 1:11-12:1 1:4-3:1 1 Sulfosulfuron 1:8-135:1 1:2-45:1 1:1-9:1 1 Tebuthiuron 1:384-3:1 1:128-1:1 1:48-1:6 1 Tefuryltrione 1:42-27:1 1:14-9:1 1:5-2:1 1 Tembotrione 1:31-37:1 1:10-13:1 1:3-3:1 1 Tepraloxydim 1:25-45:1 1:8-15:1 1:3-3:1 1 Terbacil 1:288-4:1 1:96-2:1 1:36-1:4 1 Terbuthylazine 1:857-2:1 1:285-1:3 1:107-1:12 1 Terbutryn 1:192-6:1 1:64-2:1 1:24-1:3 1 Thenylchlor 1:85-14:1 1:28-5:1 1:10-1:2 1 Thiazopyr 1:384-3:1 1:128-1:1 1:48-1:6 1 Thiencarbazone 1:3-336:1 1:1-112:1 2:1-21:1 1 Thifensulfuron-methyl 1:5-224:1 1:1-75:1 1:1 - 14:1 1 Tiafenacil 1:17-68:1 1:5-23:1 .sup.1:2- 5:1 1 Thiobencarb 1:768-2:1 1:256-1:2 1:96 - 1:11 1 Tolpyralate 1:31-37:1 1:10-13:1 .sup.1:3- 3:1 1 Topramzone 1:6-168:1 1:2-56:1 1:1- 11:1 1 Tralkoxydim 1:68-17:1 1:22-6:1 .sup.1:8- 2:1 1 Triafamone 1:2-420:1 1:1-140:1 2:1- 27:1 1 Triallate 1:768-2:1 1:256-1:2 1:96 - 1:11 1 Triasulfuron 1:5-224:1 1:1-75:1 1:1 - 14:1 1 Triaziflam 1:171-7:1 1:57-3:1 1:21 - 1:3 1 Tribenuron-methyl 1:3-336:1 1:1-112:1 2:1- 21:1 1 Triclopyr 1:192-6:1 1:64-2:1 1:24 - 1:3 1 Trifloxysulfuron 1:2-420:1 1:1-140:1 2:1- 27:1 1 Trifludimoxazin 1:25-45:1 1:8-15:1 .sup.1:3- 3:1 1 Trifluralin 1:288-4:1 1:96-2:1 1:36 - 1:4 1 Triflusulfuron-methyl 1:17-68:1 1:5-23:1 1:2 - 5:1 1 Tritosulfuron 1:13-84:1 1:4-28:1 1:1-6:1
[0717] Table A2 is constructed the same as Table A1 above except that entries below the Component (a) column heading are replaced with the respective Component (a) Column Entry shown below. Compound No. in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the Component (a) column heading all recite Compound 2 (i.e. Compound 2 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 2 with 2,4-D. Tables A3 through A64 are constructed similarly.
TABLE-US-00044 Table Number Component (a) Column Entries A2 2 A3 3 A4 4 A5 5 A6 6 A7 7 A8 8 A9 9 A10 10 A11 11 A12 12 A13 13 A14 14 A15 15 A16 16 A17 17 A18 18 A19 19 A20 20 A21 21 A22 22 A23 23 A24 24 A25 25 A26 26 A27 27 A28 28 A29 29 A30 30 A31 31 A32 32 A33 33 A34 34 A35 35 A36 36 A37 37 A38 38 A39 39 A40 40 A41 41 A42 42 A43 43 A44 44 A45 45 A46 46 A47 47 A48 48 A49 49 A50 50 A51 51 A52 52 A53 53 A54 54 A55 55 A56 56 A57 57 A58 58 A59 59 A60 60 A61 61 A62 62 A63 63 A64 64
[0718] Preferred for better control of undesired vegetation (e.g., lower use rate such as from enhanced effects, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of chlorimuron-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron, pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, metolachlor and S-metolachlor
[0719] The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Table A for compound descriptions. The following abbreviations are used in the Index Tables which follow: t is tertiary, s is secondary, n is normal, i is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, Bu is butyl, c-Pr is cyclopropyl, c-Bu is cyclobutyl, c-Pen is cyclopentyl, t-Bu is tert-butyl, i-Bu is iso-butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, NC2 is nitro, TMS is trimethylsilyl, allyl is CH.sub.2CH?CH.sub.2, propargyl is CH.sub.2C?CH and naphthyl means naphthalenyl. Some other structures are defined in the table below.
TABLE-US-00045
[0720] (R) or (S) denotes the absolute chirality of the asymmetric carbon center. The abbreviation (d) indicates that the compound appeared to decompose on melting. The abbreviation Cmpd. # stands for Compound Number. The abbreviation Ex. stands for Example and is followed by a number indicating in which example the compound is prepared. Mass spectra are reported with an estimated precision within ?0.5 Da as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H.sup.+ (molecular weight of 1) to the molecule observed by using atmospheric pressure chemical ionization (AP+).
TABLE-US-00046 INDEX TABLE A
[0721] *indicates that the compound is one of the following enantiomers.
##STR00069##
TABLE-US-00047 INDEX TABLE B
TABLE-US-00048 INDEX TABLE C
TABLE-US-00049 INDEX TABLE D
BIOLOGICAL EXAMPLES OF THE INVENTION
Test A
[0722] Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), corn (Zea mays), foxtail, giant (giant foxtail, Setaria faberi), goosegrass (Eleusine indica), kochia (Bassia scoparia), oat, wild (wild oat, Avena fatua), pigweed, palmer (palmer amaranth, Amaranthus palmeri), pigweed, redroot (redroot pigweed, Amaranthus retroflexus), ragweed (common ragweed, Ambrosia artemisiifolia), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), soybean (Glycine max), and wheat (Triticum aestivum) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
[0723] At the same time, plants selected from these crop and weed species and also galium (catchweed bedstraw, Galium aparine) and horseweed (Erigeron canadensis) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
TABLE-US-00050 TABLE A Compounds 1 2 3 4 5 6 7 8 125 g ai/ha Preemergence Barnyardgrass 100 100 Blackgrass 100 90 40 90 80 70 Corn 90 90 20 80 50 10 Foxtail, Giant 100 100 100 100 50 100 90 100 Goosegrass 100 100 90 100 100 100 Kochia 100 90 100 100 60 90 100 100 Oat, Wild 100 100 40 90 100 70 Pigweed, Palmer 100 100 50 100 100 90 Pigweed, Redroot 100 100 Ragweed 90 80 100 100 40 90 90 90 Ryegrass, Italian 100 100 100 100 90 90 100 90 Soybean 80 100 20 90 40 50 Wheat 100 100 20 100 80 50 31 g ai/ha Preemergence Barnyardgrass 80 0 Blackgrass 80 20 0 50 30 30 Corn 90 40 0 30 0 0 Foxtail, Giant 90 100 100 100 0 100 90 90 Goosegrass 70 100 10 90 80 70 Kochia 70 50 100 70 0 30 60 0 Oat, Wild 70 80 0 70 20 0 Pigweed, Palmer 100 100 10 70 50 30 Pigweed, Redroot 90 90 Ragweed 30 20 90 90 0 30 30 20 Ryegrass, Italian 100 90 90 100 20 80 100 50 Soybean 30 70 0 50 20 40 Wheat 100 70 0 80 0 0 125 g ai/ha Postemergence Barnyardgrass 90 90 Blackgrass 50 40 70 0 40 50 40 Corn 90 90 90 0 80 90 90 80 Foxtail, Giant 60 50 90 80 80 60 90 80 Galium 100 100 100 100 90 90 100 100 Goosegrass 90 90 90 90 90 90 Horseweed 90 100 90 90 Kochia 80 60 100 90 70 80 80 80 Oat, Wild 80 60 30 20 70 30 Pigweed, Palmer 60 90 70 60 60 90 Pigweed, Redroot 90 90 Ragweed 80 70 90 90 80 90 90 90 Ryegrass, Italian 70 70 90 80 40 50 90 100 Soybean 70 70 70 70 90 90 Wheat 70 70 80 50 50 60 60 70 31 g ai/ha Postemergence Barnyardgrass 80 30 Blackgrass 10 20 40 0 0 20 30 Corn 50 0 90 90 0 0 90 30 Foxtail, Giant 40 30 70 40 0 10 60 30 Galium 80 80 70 100 60 80 90 100 Goosegrass 80 70 50 80 90 80 Horseweed 70 90 80 70 Kochia 30 20 50 60 20 20 70 60 Oat, Wild 40 30 20 0 30 10 Pigweed, Palmer 40 60 20 50 30 60 Pigweed, Redroot 80 90 Ragweed 60 50 80 70 60 60 90 70 Ryegrass, Italian 70 70 90 80 20 0 50 40 Soybean 60 50 60 70 90 60 Wheat 60 70 80 50 0 60 30 60
Test B
[0724] Plant species in the flooded paddy test selected from barnyardgrass (Echinochloa crusgalli), ducksalad (Heteranthera limosa), rice (Oryza sativa), and sedge, umbrella (small-flower umbrella sedge, Cyperus difformis) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 10 to 14 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
TABLE-US-00051 TABLE B 250 g ai/ha Compounds Flood 1 2 3 4 5 6 7 8 Barnyardgrass 60 40 90 45 95 30 98 98 Ducksalad 80 75 98 100 95 85 95 95 Rice 30 10 50 0 0 10 30 35 Sedge, Umbrella 90 85 98 100 85 75 90 95
Test C
[0725] Seeds of plant species selected from blackgrass (Alopecurus myosuroides), corn (Zea mays), foxtail, giant (giant foxtail, Setaria faberi), goosegrass (Eleusine indica), kochia (Bassia scoparia), oat, wild (wild oat, Avena fatua), pigweed, palmer (palmer amaranth, Amaranthus palmeri), ragweed (common ragweed, Ambrosia artemisiifolia), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), soybean (Glycine max) and wheat (Triticum aestivum) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
[0726] At the same time, plants selected from these crop and weed species and also galium (catchweed bedstraw, Galium aparine) and horseweed (Erigeron canadensis) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 or 12 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
TABLE-US-00052 TABLE C 125 g ai/ha Preemergence Compounds 9 10 11 12 13 14 16 17 18 19 20 21 22 23 Blackgrass 100 100 100 90 0 90 0 40 100 80 90 10 Corn 100 90 100 100 100 100 0 90 0 0 90 90 90 20 Foxtail, Giant 100 100 100 100 100 100 0 100 0 10 100 100 100 90 Goosegrass 100 100 100 100 100 100 0 100 0 70 100 100 100 100 Kochia 100 100 100 100 100 100 0 100 60 70 100 90 100 90 Oat, Wild 100 100 100 100 100 60 0 100 0 40 100 90 100 90 Pigweed, Palmer 100 100 100 100 100 100 0 100 20 60 100 100 100 100 Ragweed 90 30 90 100 100 60 0 90 0 10 90 80 100 90 Ryegrass, Italian 100 100 90 100 100 100 0 100 0 0 100 100 100 100 Soybean 100 70 90 100 100 100 20 100 30 90 90 60 90 40 Wheat 100 100 100 100 100 100 0 100 0 10 100 90 100 30 125 g ai/ha Preemergence Compounds 25 26 28 29 30 31 33 34 35 36 37 38 39 40 Blackgrass 90 90 60 90 100 80 80 50 100 100 60 90 20 90 Corn 90 90 20 90 90 70 60 80 50 90 10 80 10 90 Foxtail, Giant 100 100 100 100 100 100 100 90 100 100 90 100 10 100 Goosegrass 100 100 100 100 100 100 100 100 100 100 100 100 60 100 Kochia 100 100 90 100 100 100 100 100 80 90 90 100 60 100 Oat, Wild 90 100 20 90 100 90 50 80 90 90 20 100 0 90 Pigweed, Palmer 100 100 80 100 100 100 80 100 100 100 90 100 40 100 Ragweed 100 100 100 90 100 100 80 100 90 90 90 90 80 90 Ryegrass, Italian 100 100 90 100 100 100 100 80 100 100 70 100 60 100 Soybean 90 90 80 100 90 90 60 90 90 90 30 90 60 90 Wheat 100 100 30 100 100 100 40 80 100 100 20 90 0 100 125 g ai/ha Preemergence Compounds 41 42 43 45 47 48 49 50 51 52 53 54 55 56 Blackgrass 100 70 50 90 Corn 100 70 100 100 90 60 50 90 40 90 50 30 10 10 Foxtail, Giant 100 100 100 100 100 100 90 100 90 100 90 80 10 80 Goosegrass 100 100 100 100 100 100 90 100 90 100 100 100 100 90 Kochia 100 90 80 100 100 90 70 100 80 100 50 30 10 70 Oat, Wild 100 30 50 90 100 80 90 80 50 90 90 80 20 0 Pigweed, Palmer 100 100 100 100 100 100 100 100 60 100 90 50 30 90 Ragweed 90 60 60 100 100 90 100 90 70 30 70 60 40 30 Ryegrass, Italian 100 90 100 90 90 100 100 100 100 80 100 90 60 80 Soybean 100 90 90 100 90 70 40 60 30 50 40 30 0 30 Wheat 100 90 100 100 100 80 90 100 60 100 90 80 40 0 125 g ai/ha Preemergence Compounds 57 58 59 60 61 63 64 Blackgrass 80 100 90 90 90 90 70 Corn 50 100 100 100 100 100 60 Foxtail, Giant 100 100 100 100 100 100 100 Goosegrass 100 100 100 100 100 100 100 Kochia 80 90 100 100 100 100 90 Oat, Wild 80 100 100 100 90 100 90 Pigweed, Palmer 100 100 100 100 100 100 100 Ragweed 80 90 70 100 90 100 100 Ryegrass, Italian 90 100 100 100 90 100 90 Soybean 90 100 90 90 90 100 90 Wheat 80 100 100 100 100 100 70 31 g ai/ha Preemergence Compounds 9 10 11 12 13 14 16 17 18 19 20 21 22 23 Blackgrass 60 80 90 60 0 80 0 0 80 10 50 0 Corn 50 30 50 70 40 10 0 70 0 0 60 20 90 10 Foxtail, Giant 100 90 100 100 100 80 0 90 0 0 90 100 100 20 Goosegrass 100 80 100 90 90 90 0 100 0 0 100 90 100 70 Kochia 100 90 80 100 100 50 0 80 0 0 80 60 90 20 Oat, Wild 90 90 30 90 100 10 0 90 0 0 60 30 90 40 Pigweed, Palmer 100 50 70 100 100 90 0 80 0 20 90 100 100 30 Ragweed 50 0 80 100 50 20 0 80 0 0 60 40 50 30 Ryegrass, Italian 60 50 40 90 40 40 0 100 0 0 100 70 100 30 Soybean 80 60 50 90 80 100 20 80 0 30 70 0 80 30 Wheat 90 90 90 90 90 50 0 30 0 0 70 10 90 10 31 g ai/ha Preemergence Compound 25 26 28 29 30 31 33 34 35 36 37 38 39 40 Blackgrass 80 70 50 90 80 60 20 30 70 80 10 80 0 50 Corn 30 60 0 80 90 30 30 10 30 30 0 20 0 50 Foxtail, Giant 100 90 70 90 100 90 70 90 90 50 20 80 0 100 Goosegrass 90 90 70 100 90 90 90 30 100 90 50 100 10 100 Kochia 70 100 20 90 90 100 100 90 20 20 0 100 20 90 Oat, Wild 40 60 0 90 80 60 10 30 20 30 20 30 0 10 Pigweed, Palmer 100 100 30 100 100 90 70 100 100 90 50 90 0 80 Ragweed 90 90 40 80 100 90 30 50 50 70 0 70 0 70 Ryegrass, Italian 90 90 30 100 100 60 20 40 100 100 30 80 0 90 Soybean 80 70 20 90 80 70 0 40 50 90 0 80 0 70 Wheat 60 60 20 90 90 30 10 30 20 40 0 40 0 60 31 g ai/ha Preemergence Compounds 41 42 43 45 47 48 49 50 51 52 53 54 55 56 Blackgrass 80 20 40 60 Corn 90 0 40 90 30 20 0 10 0 10 0 0 0 0 Foxtail, Giant 100 20 30 100 100 30 20 50 10 90 10 0 0 0 Goosegrass 90 50 60 100 100 80 60 90 0 80 60 20 10 10 Kochia 100 20 60 90 70 10 30 20 30 70 0 0 0 0 Oat, Wild 60 0 0 80 80 50 60 70 20 20 0 0 0 0 Pigweed, Palmer 100 80 70 100 100 100 30 90 20 70 30 0 0 10 Ragweed 70 10 10 80 70 20 100 30 0 0 60 0 0 Ryegrass, Italian 100 20 80 50 50 60 40 50 40 0 60 0 20 30 Soybean 60 0 10 50 50 30 0 30 0 30 20 0 0 0 Wheat 90 30 20 60 90 30 30 30 10 90 60 0 10 0 31 g ai/ha Preemergence Compounds 57 58 59 60 61 63 64 Blackgrass 40 80 70 80 60 70 20 Corn 0 20 40 30 20 30 10 Foxtail, Giant 80 100 100 100 100 100 100 Goosegrass 90 100 90 90 100 100 70 Kochia 60 80 80 90 90 90 70 Oat, Wild 20 90 80 90 50 70 20 Pigweed, Palmer 100 100 100 100 100 100 100 Ragweed 0 80 50 90 0 90 90 Ryegrass, Italian 70 90 30 70 60 50 50 Soybean 70 100 60 50 40 60 40 Wheat 20 90 40 40 30 80 20 125 g ai/ha Postemergence Compounds 9 10 11 12 13 14 16 17 18 19 20 21 22 23 Blackgrass 90 90 90 100 90 70 0 80 0 40 90 80 90 50 Corn 90 90 100 100 100 90 0 90 0 20 90 90 90 90 Foxtail, Giant 90 90 90 90 90 90 0 90 0 20 90 90 60 80 Galium 100 100 100 100 100 100 50 100 70 90 100 100 100 100 Goosegrass 90 90 100 100 100 90 0 90 0 90 90 90 90 90 Horseweed 100 90 70 100 90 90 30 100 0 30 90 90 90 90 Kochia 90 90 90 90 90 70 10 90 70 70 80 80 70 80 Oat, Wild 80 80 90 90 60 0 70 0 30 80 70 40 50 Pigweed, Palmer 90 90 90 100 90 90 0 90 20 10 80 70 80 70 Ragweed 80 50 80 90 90 80 90 90 50 90 90 90 80 90 Ryegrass, Italian 80 80 30 80 60 100 0 90 0 50 100 100 80 100 Soybean 80 80 100 100 100 80 60 80 80 80 70 60 70 60 Wheat 80 80 90 90 90 60 0 70 0 10 70 50 60 60 125 g ai/ha Postemergence Compounds 25 26 28 29 30 31 33 34 35 36 37 38 39 40 Blackgrass 90 90 70 70 90 100 60 60 60 30 60 70 10 60 Corn 60 90 30 90 90 90 90 90 90 20 90 90 10 100 Foxtail, Giant 30 90 70 90 80 90 90 90 90 30 80 90 10 90 Galium 100 100 100 100 100 100 100 100 100 80 90 100 90 100 Goosegrass 90 100 70 90 90 100 90 80 90 90 90 90 30 90 Horseweed 100 100 100 100 70 80 100 90 80 Kochia 90 90 80 90 90 90 90 90 90 80 70 90 60 90 Oat, Wild 20 50 30 80 80 90 70 70 70 30 70 60 20 80 Pigweed, Palmer 90 90 90 90 90 90 80 100 70 70 30 80 20 90 Ragweed 80 80 80 80 90 90 90 90 90 90 90 90 80 80 Ryegrass, Italian 70 100 40 100 100 90 90 90 60 40 60 70 30 80 Soybean 100 100 60 100 60 70 100 70 60 70 70 80 90 80 Wheat 60 70 60 70 70 80 70 80 60 60 60 60 60 70 125 g ai/ha Postemergence Compounds 41 42 43 45 47 48 49 50 51 52 53 54 55 56 Blackgrass 60 50 50 40 70 30 60 40 20 40 60 90 40 20 Corn 90 90 90 90 90 50 100 90 60 60 60 80 70 30 Foxtail, Giant 90 90 90 80 90 60 90 80 40 50 90 70 70 40 Galium 100 90 90 100 90 100 90 100 90 100 Goosegrass 90 90 90 90 90 40 80 80 20 70 90 90 90 60 Horseweed 100 80 60 90 100 90 100 90 90 90 90 80 80 Kochia 80 60 60 100 80 60 60 70 70 70 50 50 20 30 Oat, Wild 30 40 20 30 60 20 70 50 30 60 50 80 30 10 Pigweed, Palmer 90 70 90 90 70 70 50 60 60 40 70 50 40 40 Ragweed 70 90 90 80 80 80 90 80 80 70 90 80 80 60 Ryegrass, Italian 100 70 70 50 90 60 90 90 50 100 70 70 60 60 Soybean 90 80 90 100 90 70 80 80 60 70 60 60 70 50 Wheat 60 80 70 60 80 70 70 80 70 70 80 70 70 70 125 g ai/ha Postemergence Compounds 57 58 59 60 61 63 64 Blackgrass 80 70 80 90 70 30 20 Corn 40 90 90 100 60 50 10 Foxtail, Giant 70 90 90 90 50 30 20 Galium 90 90 100 100 90 100 100 Goosegrass 90 100 90 90 90 90 70 Horseweed 80 90 80 100 60 90 60 Kochia 70 90 80 90 90 90 100 Oat, Wild 10 90 90 90 80 40 10 Pigweed, Palmer 70 80 80 90 80 90 70 Ragweed 60 90 70 90 80 80 70 Ryegrass, Italian 60 70 70 70 60 10 20 Soybean 100 90 80 100 90 100 90 Wheat 70 70 80 90 80 40 20 31 g ai/ha Postemergence Compounds 9 10 11 12 13 14 16 17 18 19 20 21 22 23 Blackgrass 80 60 40 80 80 10 0 70 0 0 90 40 20 10 Corn 90 90 90 100 100 70 0 90 0 0 90 90 50 30 Foxtail, Giant 40 40 60 90 60 20 0 90 0 0 80 40 20 0 Galium 90 100 80 100 100 100 50 90 10 30 90 100 100 90 Goosegrass 90 90 90 100 70 60 0 90 0 0 90 90 70 30 Horseweed 100 80 20 90 70 90 0 70 0 10 60 60 90 80 Kochia 80 60 40 90 90 50 20 80 20 30 70 70 60 30 Oat, Wild 80 80 90 90 30 0 30 0 0 30 40 20 20 Pigweed, Palmer 70 60 40 80 80 40 0 40 0 0 50 30 50 50 Ragweed 70 50 60 90 80 60 80 70 0 60 80 80 60 90 Ryegrass, Italian 50 80 0 70 60 60 0 60 0 0 60 50 70 50 Soybean 80 80 100 100 100 80 40 60 50 80 60 60 60 60 Wheat 80 80 80 80 90 60 0 70 0 0 70 10 50 10 31 g ai/ha Postemergence Compounds 25 26 28 29 30 31 33 34 35 36 37 38 39 40 Blackgrass 0 40 10 60 50 50 0 30 50 20 0 40 0 10 Corn 30 50 10 80 90 70 80 60 50 0 10 80 0 80 Foxtail, Giant 30 40 30 90 50 30 50 40 40 10 10 50 0 50 Galium 100 100 90 80 80 100 100 100 70 60 60 90 80 80 Goosegrass 50 80 30 90 80 60 60 30 70 30 0 30 0 50 Horseweed 100 70 90 90 40 80 90 70 80 Kochia 60 70 50 60 80 80 80 80 50 40 50 80 30 70 Oat, Wild 0 20 20 20 50 60 30 30 40 30 20 50 0 50 Pigweed, Palmer 70 70 50 60 60 70 20 70 40 30 0 50 0 30 Ragweed 60 60 80 60 90 90 90 90 60 40 60 80 30 60 Ryegrass, Italian 20 60 40 70 90 40 20 40 50 0 0 30 0 60 Soybean 100 70 50 60 50 60 80 60 60 70 60 70 50 70 Wheat 50 60 20 70 70 60 50 70 60 60 10 60 0 60 31 g ai/ha Postemergence Compounds 41 42 43 45 47 48 49 50 51 52 53 54 55 56 Blackgrass 40 0 0 10 40 10 30 10 10 20 20 30 0 0 Corn 40 20 40 20 70 0 50 30 0 0 20 0 0 0 Foxtail, Giant 20 20 10 30 70 20 60 50 0 0 30 30 30 10 Galium 100 50 70 100 80 90 80 60 60 70 Goosegrass 90 40 20 70 50 0 20 20 0 0 60 60 40 0 Horseweed 70 20 30 30 70 60 80 80 70 80 20 Kochia 70 10 20 70 40 20 40 20 30 20 20 30 0 0 Oat, Wild 30 0 10 10 10 10 30 20 0 10 10 10 20 10 Pigweed, Palmer 50 50 40 70 30 30 10 20 10 0 40 0 0 0 Ragweed 50 40 50 50 60 30 70 70 60 40 70 50 50 20 Ryegrass, Italian 30 20 30 0 50 40 50 50 20 40 0 60 0 0 Soybean 90 70 80 80 70 30 60 60 30 60 50 50 50 40 Wheat 60 0 30 20 80 30 70 60 20 20 40 30 20 0 31 g ai/ha Postemergence Compounds 57 58 59 60 61 63 64 Blackgrass 40 50 10 50 30 0 0 Corn 0 60 20 90 10 0 0 Foxtail, Giant 60 60 10 80 20 0 0 Galium 50 90 100 100 70 100 100 Goosegrass 70 100 70 80 40 0 30 Horseweed 0 90 20 80 60 90 10 Kochia 50 70 70 100 60 80 50 Oat, Wild 10 60 30 30 20 0 0 Pigweed, Palmer 40 50 40 60 50 70 60 Ragweed 40 70 10 80 50 40 30 Ryegrass, Italian 20 60 10 50 0 0 0 Soybean 80 60 60 80 60 50 60 Wheat 70 70 50 80 70 10 0
Test D
[0727] Plant species in the flooded paddy test selected from barnyardgrass (Echinochloa crusgalli), ducksalad (Heteranthera limosa), rice (Oryza sativa), and sedge, umbrella (small-flower umbrella sedge, Cyperus difformis) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
TABLE-US-00053 TABLE D 250 g ai/ha Flood Compounds 9 10 11 12 13 14 16 17 18 19 20 21 22 23 Barnyardgrass 10 0 25 0 10 0 0 85 0 0 90 95 90 95 Ducksalad 95 90 100 100 100 65 0 95 0 0 90 98 90 80 Rice 30 0 45 40 35 25 0 15 0 0 15 85 55 40 Sedge, Umbrella 85 80 100 100 100 35 0 95 0 0 98 98 95 95 250 g ai/ha Flood Compounds 25 26 28 29 30 31 33 34 35 36 37 38 39 40 Barnyardgrass 0 30 60 95 95 30 90 35 0 0 90 0 35 0 Ducksalad 75 75 70 45 90 75 80 65 55 65 70 65 55 70 Rice 15 65 30 85 75 30 45 25 0 0 0 0 0 0 Sedge, Umbrella 90 95 95 95 98 80 90 80 95 95 95 75 95 90 250 g ai/ha Flood Compounds 41 42 43 45 47 48 49 50 51 52 53 54 55 56 Barnyardgrass 15 0 25 95 75 80 100 90 100 20 40 45 50 35 Ducksalad 60 95 95 85 95 95 95 90 85 90 70 90 90 85 Rice 10 15 30 55 30 25 40 20 10 0 25 0 15 0 Sedge, Umbrella 70 90 95 90 95 90 90 95 90 80 98 98 95 95 250 g ai/ha Flood Compounds 57 58 59 60 61 63 64 Barnyardgrass 15 90 60 90 95 45 25 Ducksalad 90 80 80 90 75 95 80 Rice 10 60 40 35 20 45 15 Sedge, Umbrella 95 95 95 95 90 95 95