Herbicidally active 2-(substituted-phenyl)-cyclopentane-1,3-dione compounds and derivatives thereof
10375956 ยท 2019-08-13
Assignee
Inventors
- Ian Henry Aspinall (Bracknell, GB)
- Stephane Andre Marie Jeanmart (Stein, CH)
- James Nicholas Scutt (Bracknell, GB)
- John Benjamin Taylor (Bracknell, GB)
Cpc classification
C07C49/683
CHEMISTRY; METALLURGY
A01N37/08
HUMAN NECESSITIES
A01N37/02
HUMAN NECESSITIES
A01N35/06
HUMAN NECESSITIES
C07C69/013
CHEMISTRY; METALLURGY
International classification
A01N35/06
HUMAN NECESSITIES
C07C49/683
CHEMISTRY; METALLURGY
C07C49/753
CHEMISTRY; METALLURGY
C07C69/013
CHEMISTRY; METALLURGY
A01N37/02
HUMAN NECESSITIES
Abstract
The present invention relates to a compound of formula (I): wherein: R.sup.8 and R.sup.9, independently of each other, are hydrogen, fluorine or C.sub.1-C.sub.3alkyl; R.sup.10 is hydrogen or methyl (preferably hydrogen); and the other substituents are as defined herein; and wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are thought to be suitable for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledonous weeds, in crops of useful plants, comprising applying a compound of formula (I), or a herbicidal composition comprising such a compound, to the plants or to the locus thereof. ##STR00001##
Claims
1. A compound of formula (I): ##STR00182## wherein: R.sup.1 is methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, difluoromethoxy or trifluoromethoxy; and either (a): R.sup.2 is R.sup.2A and R.sup.3 is R.sup.3A; or (b): R.sup.2 is R.sup.2B and R.sup.3 is R.sup.3B; wherein: R.sup.3A is hydrogen, methyl, fluorine or chlorine; and R.sup.2A is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, C.sub.1-C.sub.2fluoroalkyl, vinyl, prop-1-enyl, CCR.sup.2AA, halogen, or (C.sub.1-C.sub.2fluoroalkyl)-methoxy-; wherein R.sup.2AA is hydrogen, fluorine, trifluoromethyl, ethyl or cyclopropyl; or R.sup.2A is phenyl optionally substituted by 1, 2 or 3 substituents independently being halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, methoxymethyl, vinyl, ethynyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.2fluoroalkoxy, methylthio, methylsulfinyl, methylsulfonyl, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, methylthio, methylsulfinyl, methylsulfonyl or nitro; or R.sup.2A is monocyclic heteroaryl optionally substituted by 1, 2 or 3 substituents independently being halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, methoxymethyl, vinyl, ethynyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.2fluoroalkoxy, methylthio, methylsulfinyl, methylsulfonyl, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, methylthio, methylsulfinyl, methylsulfonyl or nitro; and wherein R.sup.2B is hydrogen, methyl or fluorine; and either R.sup.3B is phenyl optionally substituted by 1, 2 or 3 substituents independently being halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, methoxymethyl, vinyl, ethynyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, methylthio, methylsulfinyl, methylsulfonyl, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, methylthio, methylsulfinyl, methylsulfonyl or nitro; or R.sup.3B is monocyclic heteroaryl optionally substituted by 1, 2 or 3 substituents independently being halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, methoxymethyl, vinyl, ethynyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, methylthio, methylsulfinyl, methylsulfonyl, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, methylthio, methylsulfinyl, methylsulfonyl or nitro; and wherein R.sup.4 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.2fluoroalkoxy, C.sub.1-C.sub.2alkoxy-C.sub.1-C.sub.3alkoxy-, or C.sub.1fluoroalkoxy-C.sub.1-C.sub.3alkoxy-; and R.sup.5, R.sup.6 and R.sup.7, independently of each other, are hydrogen, C.sub.1-C.sub.5alkyl, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3alkynyl, C.sub.1-C.sub.2fluoroalkyl or C.sub.1-C.sub.2alkoxyC.sub.1-C.sub.2alkyl; provided that: either (i) at least two of R.sup.5, R.sup.6 and R.sup.7 are hydrogen, or (ii) two of R.sup.5, R.sup.6 and R.sup.7 are methyl and the remaining one of R.sup.5, R.sup.6 and R.sup.7 is hydrogen; and R.sup.8 and R.sup.9, independently of each other, are hydrogen, fluorine or C.sub.1-C.sub.3alkyl; and R.sup.10 is hydrogen or methyl; and wherein: G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group; or G is C(X.sup.a)R.sup.a, C(X.sup.b)X.sup.cR.sup.b, C(X.sup.d)N(R.sup.c)R.sup.d, SO.sub.2R.sup.e, P(X.sup.e)(R.sup.f)R.sup.g, CH.sub.2X.sup.fR.sup.h; or phenyl-CH.sub.2 or phenyl-CH(C.sub.1-C.sub.2alkyl)- (in each of which the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or heteroaryl-CH.sub.2 or heteroaryl-CH(C.sub.1-C.sub.2alkyl)- (in each of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or phenyl-C(O)CH.sub.2 (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro); or C.sub.1-C.sub.6alkoxy-C(O)CH.sub.2, C.sub.1-C.sub.6alkyl-C(O)CH.sub.2, C.sub.1-C.sub.6alkoxy-C(O)CHCH, C.sub.2-C.sub.7alken-1-yl-CH.sub.2, C.sub.2-C.sub.7alken-1-yl-CH(C.sub.1-C.sub.2alkyl)-, C.sub.2-C.sub.4fluoroalken-1-yl-CH.sub.2, C.sub.2-C.sub.7alkyn-1-yl-CH.sub.2, or C.sub.2-C.sub.7alkyn-1-yl-CH(C.sub.1-C.sub.2alkyl)-; wherein X.sup.a, X.sup.b, X.sup.c, X.sup.d, X.sup.e and X.sup.f are independently of each other oxygen or sulfur; and wherein R.sup.a is H, C.sub.1-C.sub.21alkyl, C.sub.2-C.sub.21alkenyl, C.sub.2-C.sub.18 alkynyl, C.sub.1-C.sub.10fluoroalkyl, C.sub.1-C.sub.10cyanoalkyl, C.sub.1-C.sub.10nitroalkyl, C.sub.1-C.sub.10aminoalkyl, C.sub.1-C.sub.5alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.7cycloalkyl(C C.sub.1-C.sub.5alkoxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkenyloxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkynyloxy (C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylthio(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfinyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8alkylideneaminoxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxycarbonyl(C.sub.1-C.sub.5)alkyl, aminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonylamino(C.sub.1-C.sub.5)alkyl, N(C.sub.1-C.sub.5)alkylcarbonyl-N(C.sub.1-C.sub.5)alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.6trialkylsilyl(C.sub.1-C.sub.5)alkyl, phenyl(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C.sub.1-C.sub.5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), C.sub.2-C.sub.5fluoroalkenyl, C.sub.3-C.sub.8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; R.sup.b is C.sub.1-C.sub.18alkyl, C.sub.3-C.sub.18alkenyl, C.sub.3-C.sub.18alkynyl, C.sub.2-C.sub.10fluoroalkyl, C.sub.1-C.sub.10cyanoalkyl, C.sub.1-C.sub.10nitroalkyl, C.sub.2-C.sub.10aminoalkyl, C.sub.1-C.sub.5alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.7cycloalkyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkenyloxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkynyloxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylthio(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfinyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8alkylideneaminoxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxycarbonyl(C.sub.1-C.sub.5)alkyl, aminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonylamino(C.sub.1-C.sub.5)alkyl, N(C.sub.1-C.sub.5)alkylcarbonyl-N(C.sub.1-C.sub.5)alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.6trialkylsilyl(C.sub.1-C.sub.5)alkyl, phenyl(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), heteroarylC.sub.1-C.sub.5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkyl-thio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), C.sub.3-C.sub.5fluoroalkenyl, C.sub.3-C.sub.8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; and R.sup.c and R.sup.d are each independently of each other hydrogen, C.sub.1-C.sub.10alkyl, C.sub.3-C.sub.10alkenyl, C.sub.3-C.sub.10alkynyl, C.sub.2-C.sub.10fluoroalkyl, C.sub.1-C.sub.10cyanoalkyl, C.sub.1-C.sub.10nitroalkyl, C.sub.1-C.sub.10aminoalkyl, C.sub.1-C.sub.5alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.7cycloalkyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkenyloxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkynyloxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylthio(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfinyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8alkylideneaminoxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxycarbonyl(C.sub.1-C.sub.5)alkyl, aminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonylamino(C.sub.1-C.sub.5)alkyl, N(C.sub.1-C.sub.5)alkylcarbonyl-N(C.sub.2-C.sub.5)alkylaminoalkyl, C.sub.3-C.sub.6trialkylsilyl(C.sub.1-C.sub.5)alkyl, phenyl(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C.sub.1-C.sub.5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), C.sub.2-C.sub.5fluoroalkenyl, C.sub.3-C.sub.8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; or C.sub.3-C.sub.7cycloalkylamino, di(C.sub.3-C.sub.7cycloalkyl)amino or C.sub.3-C.sub.7cycloalkoxy; or R.sup.c and R.sup.d, together with the nitrogen to which they are bonded, to form an unsubstituted 4, 5, 6 or 7 (e.g. 5 or 6) membered ring, optionally containing one heteroatom selected from O or S; and R.sup.e is C.sub.1-C.sub.10alkyl, C.sub.2-C.sub.10alkenyl, C.sub.2-C.sub.10alkynyl, C.sub.1-C.sub.10fluoroalkyl, C.sub.1-C.sub.10cyanoalkyl, C.sub.1-C.sub.10nitroalkyl, C.sub.1-C.sub.10aminoalkyl, C.sub.1-C.sub.5alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.7cycloalkyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkenyloxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkynyloxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylthio(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfinyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8alkylideneaminoxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxycarbonyl(C.sub.1-C.sub.5)alkyl, aminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonylamino(C.sub.1-C.sub.5)alkyl, N(C.sub.1-C.sub.5)alkylcarbonyl-N(C.sub.1-C.sub.5)alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.6trialkylsilyl(C.sub.1-C.sub.5)alkyl, phenyl(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C.sub.1-C.sub.5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), C.sub.2-C.sub.5fluoroalkenyl, C.sub.3-C.sub.8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; or C.sub.3-C.sub.7cycloalkylamino, di(C.sub.3-C.sub.7cycloalkyl)amino, C.sub.3-C.sub.7cycloalkoxy, C.sub.1-C.sub.10alkoxy, C.sub.1-C.sub.10fluoroalkoxy, C.sub.1-C.sub.5alkylamino or di(C.sub.1-C.sub.4alkyl)amino; R.sup.f and R.sup.g are are each independently of each other C.sub.1-C.sub.10alkyl, C.sub.2-C.sub.10alkenyl, C.sub.2-C.sub.10alkynyl, C.sub.1-C.sub.10alkoxy, C.sub.1-C.sub.10fluoroalkyl, C.sub.1-C.sub.10cyanoalkyl, C.sub.1-C.sub.10nitroalkyl, C.sub.1-C.sub.10aminoalkyl, C.sub.1-C.sub.5alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.7cycloalkyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkenyloxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkynyloxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylthio(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfinyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8alkylideneaminoxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxycarbonyl(C.sub.1-C.sub.5)alkyl, aminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonylamino(C.sub.1-C.sub.5)alkyl, N(C.sub.1-C.sub.5)alkylcarbonyl-N(C.sub.2-C.sub.5)alkylaminoalkyl, C.sub.3-C.sub.6trialkylsilyl(C.sub.1-C.sub.5)alkyl, phenyl(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C.sub.1-C.sub.5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, halogen, cyano, or nitro), C.sub.2-C.sub.5fluoroalkenyl, C.sub.3-C.sub.8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; or C.sub.3-C.sub.7cycloalkylamino, di(C.sub.3-C.sub.7cycloalkyl)amino, C.sub.3-C.sub.7cycloalkoxy, C.sub.1-C.sub.10fluoroalkoxy, C.sub.1-C.sub.5alkylamino or di(C.sub.1-C.sub.4alkyl)amino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; and R.sup.h is C.sub.1-C.sub.10alkyl, C.sub.3-C.sub.10alkenyl, C.sub.3-C.sub.10alkynyl, C.sub.1-C.sub.10fluoroalkyl, C.sub.1-C.sub.10cyanoalkyl, C.sub.1-C.sub.10nitroalkyl, C.sub.2-C.sub.10aminoalkyl, C.sub.1-C.sub.5alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.7cycloalkyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkenyloxy(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.5alkynyloxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylthio(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfinyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylsulfonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8alkylideneaminoxy(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkoxycarbonyl(C.sub.1-C.sub.5)alkyl, aminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.2-C.sub.8dialkylaminocarbonyl(C.sub.1-C.sub.5)alkyl, C.sub.1-C.sub.5alkylcarbonylamino(C.sub.1-C.sub.5)alkyl, N(C.sub.1-C.sub.5)alkylcarbonyl-N(C.sub.1-C.sub.5)alkylamino(C.sub.1-C.sub.5)alkyl, C.sub.3-C.sub.6trialkylsilyl(C.sub.1-C.sub.5)alkyl, phenyl(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, halogen, cyano or nitro), heteroaryl(C.sub.1-C.sub.5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, halogen, cyano or nitro), phenoxy(C.sub.1-C.sub.5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, halogen, cyano or nitro), heteroaryloxy(C.sub.1-C.sub.5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, halogen, cyano or nitro), C.sub.3-C.sub.5fluoroalkenyl, C.sub.3-C.sub.8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3fluoroalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3fluoroalkoxy, halogen, cyano or nitro; C.sub.1-C.sub.6alkyl-C(O); or phenyl-C(O) wherein the phenyl is optionally substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; wherein heteroaryl means an aromatic ring system containing at least one ring heteroatom and consisting either of a single ring or of two fused rings; and wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof.
2. The compound as claimed in claim 1, wherein G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group; or G is C(X.sup.a)R.sup.a or C(X.sup.b)X.sup.cR.sup.b.
3. The compound as claimed in claim 1, wherein X.sup.a, X.sup.b and X.sup.c are oxygen; R.sup.a is C.sub.1-C.sub.10alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-methyl-, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, phenyl-methyl- (in which the phenyl is optionally substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1 fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1 fluoroalkoxy, fluorine, chlorine or cyano); phenyl or phenyl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; or monocyclic heteroaryl or monocyclic heteroaryl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; and R.sup.b is C.sub.1-C.sub.10alkyl, C.sub.2-C.sub.5alkenyl-CH.sub.2, C.sub.2-C.sub.4alkenyl-CH(Me)-, C.sub.2-C.sub.5alkynyl-CH.sub.2, C.sub.2-C.sub.4alkynyl-CH(Me)-, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-methyl-, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.4alkyl, phenyl-methyl- (in which the phenyl is optionally substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano); phenyl or phenyl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; or monocyclic heteroaryl or monocyclic heteroaryl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano.
4. The compound as claimed in claim 1, wherein R.sup.1 is methyl, ethyl, ethynyl, fluorine, chlorine, bromine, methoxy, difluoromethoxy or trifluoromethoxy.
5. The compound as claimed in claim 1, wherein R.sup.1 is methyl, fluorine or chlorine.
6. The compound as claimed in claim 1, wherein R.sup.2 is R.sup.2A and R.sup.3 is R.sup.3A.
7. The compound as claimed in claim 1, wherein R.sup.3A is hydrogen.
8. The compound as claimed in claim 1, wherein: R.sup.2A is methyl, ethyl, vinyl, prop-1-enyl, CCR.sup.2AA, halogen, or C.sub.1fluoroalkyl-methoxy-; or R.sup.2A is phenyl optionally substituted by 1, 2 or 3 substituents independently being halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2alkoxy or nitro; or R.sup.2A is monocyclic 6-membered or 5-membered heteroaryl optionally substituted by 1, 2 or 3 substituents independently being halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2alkoxy or nitro.
9. The compound as claimed in claim 1, wherein: when R.sup.2A is optionally substituted phenyl, then R.sup.2A is of sub-formula (a) or (a1): ##STR00183## in which: R.sup.11 is hydrogen, fluorine or chlorine; R.sup.12 is halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro; R.sup.13 is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro; and R.sup.14 is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro; provided that one or more of R.sup.11, R.sup.13 and R.sup.14 are hydrogen; and provided that either one or none (i.e. no more than one) of R.sup.12, R.sup.13 and R.sup.14 are C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2alkoxy or nitro; and R.sup.12AA is hydrogen, fluorine or chlorine; R.sup.13AA is fluorine or chlorine; and R.sup.16 is hydrogen, fluorine or chlorine; provided that when R.sup.12AA is fluorine or chlorine, then R.sup.16 is fluorine or chlorine; and provided that either one or none (i.e. no more than one) of R.sup.13AA and R.sup.16 are chlorine; and wherein, when R.sup.2A is optionally substituted monocyclic heteroaryl, then R.sup.2A is of sub-formula (b), (c), (d), (e), (f) or (g): ##STR00184## in which: R.sup.12A is halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro; R.sup.13A is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro; and R.sup.14A is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro; provided that either one or none (i.e. no more than one) of R.sup.12A, R.sup.13A and R.sup.14A are C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2alkoxy or nitro; and R.sup.15 is hydrogen, halogen, methyl, C.sub.1fluoroalkyl, C.sub.1fluoroalkoxy, or cyano.
10. The compound as claimed in claim 9, wherein: when R.sup.2A is optionally substituted phenyl, then R.sup.2A is of sub-formula (a), wherein: R.sup.11 is hydrogen; R.sup.12 is fluorine, chlorine, bromine, C.sub.1fluoroalkyl, C.sub.1fluoroalkoxy, or cyano; R.sup.13 is hydrogen, fluorine or chlorine; and R.sup.14 is hydrogen, fluorine, chlorine, bromine, or C.sub.1fluoroalkyl; and when R.sup.2A is optionally substituted monocyclic heteroaryl, then R.sup.2A is of sub-formula (b), (c), or (g), wherein: R.sup.12A is fluorine, chlorine, bromine, C.sub.1fluoroalkyl, C.sub.1fluoroalkoxy, or cyano; R.sup.13A is hydrogen, fluorine or chlorine; and R.sup.14A is hydrogen, fluorine, chlorine, bromine, or C.sub.1fluoroalkyl; and R.sup.15 is hydrogen, fluorine, chlorine, methyl, C.sub.1fluoroalkyl, or C.sub.1fluoroalkoxy.
11. The compound as claimed in claim 1, wherein: when R.sup.3B is optionally substituted phenyl, then R.sup.3B is of sub-formula (a2): ##STR00185## in which R.sup.11B is hydrogen, fluorine, chlorine, methyl or methoxy; R.sup.12B is fluorine, chlorine, C.sub.1fluoroalkyl, methoxy or C.sub.1fluoroalkoxy; R.sup.13B is hydrogen or fluorine; and R.sup.14B is hydrogen or fluorine; provided that one or more of R.sup.11B, R.sup.13B and R.sup.14B are hydrogen; and wherein, when R.sup.3B is optionally substituted monocyclic heteroaryl, then R.sup.3B is of sub-formula (b1) or (c1): ##STR00186## in which: R.sup.12B is fluorine, chlorine, C.sub.1fluoroalkyl, methoxy or C.sub.1fluoroalkoxy; R.sup.13B is hydrogen or fluorine; and R.sup.14B is hydrogen, fluorine or chlorine.
12. The compound as claimed in claim 1, wherein: R.sup.3B is of sub-formula (a2): ##STR00187## R.sup.11B is hydrogen, fluorine, chlorine, methyl or methoxy, R.sup.12B is fluorine, chlorine, C.sub.1fluoroalkyl, methoxy or C.sub.1fluoroalkoxy, R.sup.13B is hydrogen or fluorine, and R.sup.14B is hydrogen or fluorine, provided that one or more of R.sup.11B, R.sup.13B and R.sup.14B are hydrogen; and R.sup.2B is hydrogen.
13. A compound as claimed in claim 1, wherein: R.sup.1 is methyl, fluorine, chlorine, bromine, difluoromethoxy or trifluoromethoxy; and either (a): R.sup.2 is R.sup.2A and R.sup.3 is R.sup.3A; or (b): R.sup.2 is R.sup.2B and R.sup.3 is R.sup.3B; and wherein: R.sup.3A is hydrogen or methyl; and R.sup.2A is methyl, CCR.sup.2AA chlorine or bromine; or R.sup.2A is of sub-formula (a) or (a1): ##STR00188## in which: R.sup.11 is hydrogen, fluorine or chlorine, R.sup.12 is halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro, R.sup.13 is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro, and R.sup.14 is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro, provided that one or more of R.sup.11, R.sup.13 and R.sup.14 are hydrogen; and provided that either one or none (i.e. no more than one) of R.sup.12, R.sup.13 and R.sup.14 are C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2alkoxy or nitro, and R.sup.12AA is hydrogen, fluorine or chlorine, R.sup.13AA is fluorine or chlorine, and R.sup.16 is hydrogen, fluorine or chlorine, provided that when R.sup.12AA is fluorine or chlorine, then R.sup.16 is fluorine or chlorine, and provided that either one or none (i.e. no more than one) of R.sup.13AA and R.sup.16 are chlorine; or R.sup.2A is of sub-formula (b), (c), (d), (e), (f) or (g): ##STR00189## in which: R.sup.12A is halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.1fluoroalkoxy, cyano or nitro, R.sup.13A is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoro alkoxy, cyano or nitro, and R.sup.14A is hydrogen, halogen, C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1-C.sub.2fluoroalkoxy, cyano or nitro, provided that either one or none (i.e. no more than one) of R.sup.12A, R.sup.13A and R.sup.14A are C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.2alkoxy or nitro, and R.sup.15 is hydrogen, halogen, methyl, C.sub.1fluoroalkyl, C.sub.1fluoroalkoxy, or cyano; and R.sup.2B is hydrogen or methyl; and either R.sup.3B is of sub-formula (a2): ##STR00190## in which R.sup.11B is hydrogen, fluorine, chlorine, methyl or methoxy, R.sup.12B is fluorine, chlorine, C.sub.1fluoroalkyl, methoxy or C.sub.1fluoroalkoxy, R.sup.13B is hydrogen or fluorine, and R.sup.14B is hydrogen or fluorine, provided that one or more of R.sup.11B, R.sup.13B and R.sup.14B are hydrogen, or R.sup.3B is of sub-formula (b1) or (c1): ##STR00191## in which: R.sup.12B is fluorine, chlorine, C.sub.1fluoroalkyl, methoxy or C.sub.1fluoroalkoxy, R.sup.13B is hydrogen or fluorine, and R.sup.14B is hydrogen, fluorine or chlorine; and wherein: when R.sup.2 is R.sup.2A and R.sup.3 is R.sup.3A, then R.sup.4 is methyl, ethyl, ethynyl, fluorine, chlorine, methoxy, ethoxy, n-propoxy, C.sub.1-C.sub.2fluoroalkoxy, or MeOCH.sub.2CH.sub.2O; and, when R.sup.2 is R.sup.2B and R.sup.3 is R.sup.3B, then R.sup.4 is hydrogen, methyl, fluorine or chlorine.
14. The compound as claimed in claim 13, wherein: when R.sup.2 is R.sup.2A and R.sup.3 is R.sup.3A, then R.sup.4 is methyl, chlorine or methoxy; and when R.sup.2 is R.sup.2B and R.sup.3 is R.sup.3B, then R.sup.4 is hydrogen.
15. The compound as claimed in claim 1, wherein all of R.sup.5, R.sup.6 and R.sup.7 are hydrogen.
16. The compound as claimed in claim 1, wherein R.sup.8 and R.sup.9 are both hydrogen.
17. The compound as claimed in claim 1, wherein R.sup.10 is hydrogen.
18. The compound as claimed in claim 1, wherein the compound of formula (I) is a compound of formula (IC): ##STR00192## and wherein 40% or more by molarity of the compound of formula (IC) has the indicated stereochemistry at the ring-carbon atom bonded to R.sup.5 and CR.sup.8R.sup.9CCR.sup.10.
19. The compound as claimed in claim 1, which is any of compounds: ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## present either as a free compound and/or present as an agrochemically acceptable salt thereof.
20. The compound as claimed in claim 1, wherein the compound has the formula: ##STR00201## wherein R.sup.1 is methyl, R.sup.4 is methyl, R.sup.10 is hydrogen and R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00202## wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00203## wherein R.sup.1 is methyl, R.sup.4 is ethyl, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00204## wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00205## wherein R.sup.1 is methyl, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00206## wherein R.sup.1 is methyl, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00207## wherein R.sup.1 is methyl, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00208## wherein R.sup.1 is methyl, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00209## wherein R.sup.1 is chloro, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00210## wherein R.sup.1 is chloro, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00211## wherein R.sup.1 is chloro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen ##STR00212## wherein R.sup.1 is chloro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00213## wherein R.sup.1 is fluoro, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00214## wherein R.sup.1 is fluoro, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen ##STR00215## wherein R.sup.1 is fluoro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00216## wherein R.sup.1 is fluoro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00217## wherein R.sup.1 is bromo, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00218## wherein R.sup.1 is bromo, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00219## wherein R.sup.1 is bromo, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00220## wherein R.sup.1 is bromo, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00221## wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00222## wherein R.sup.1 is chloro, R.sup.4 is chloro, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00223## wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00224## wherein R.sup.1 is bromo, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00225## wherein R.sup.1 is fluoro, R.sup.4 is fluoro, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00226## wherein R.sup.1 is fluoro, R.sup.4 is chloro, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00227## wherein R.sup.1 is methyl, R.sup.4 is methyl, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00228## wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00229## wherein R.sup.1 is methyl, R.sup.4 is ethyl, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00230## wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00231## wherein R.sup.1 is methyl, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00232## wherein R.sup.1 is methyl, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00233## wherein R.sup.1 is methyl, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00234## wherein R.sup.1 is methyl, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00235## wherein R.sup.1 is chloro, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00236## wherein R.sup.1 is chloro, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00237## wherein R.sup.1 is chloro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00238## wherein R.sup.1 is chloro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00239## wherein R.sup.1 is fluoro, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00240## wherein R.sup.1 is fluoro, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00241## wherein R.sup.1 is fluoro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00242## wherein R.sup.1 is fluoro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00243## wherein R.sup.1 is bromo, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00244## wherein R.sup.1 is bromo, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00245## wherein R.sup.1 is bromo, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00246## wherein R.sup.1 is bromo, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00247## wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00248## wherein R.sup.1 is chloro, R.sup.4 is chloro, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00249## wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen ##STR00250## wherein R.sup.1 is bromo, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00251## wherein R.sup.1 is fluoro, R.sup.4 is fluoro, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00252## wherein R.sup.1 is fluoro, R.sup.4 is chloro, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, and R.sup.2 is selected from the group consisting of: phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 4-methylphenyl, 4-cyanophenyl, 4-methoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-methylthiophenyl, 4-methylsulfinylphenyl, 4-methylsulfonylphenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-2-methoxyphenyl, 4-chloro-3-methoxyphenyl, 4-chloro-2-methylphenyl, 4-chloro-3-methylphenyl, 2-fluoro-4-cyanophenyl, 2-chloropyridin-5-yl, 5-chloropyridin-2-yl, 3-fluoro-5-chloropyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, 5-fluoropyridin-2-yl, 5-bromopyridin-2-yl, 6-chloropyridazin-3-yl, 5-bromopyrimidin-2-yl, 5-chloropyrimidin-2-yl, 5-fluoropyrimidin-2-yl, 4-chlorothien-2-yl, 5-chlorothien-2-yl, 3-chloropyrazol-1-yl, and 4-chloropyrazol-1-yl; or wherein the compound has the formula: ##STR00253## wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00254## wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00255## wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00256## wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00257## wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00258## wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00259## wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, or ##STR00260## wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen, and R.sup.3 is selected from the group consisting of: phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 4-methylphenyl, 4-cyanophenyl, 4-methoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-methylthiophenyl, 4-methylsulfinylphenyl, 4-methylsulfonylphenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-2-methoxyphenyl, 4-chloro-3-methoxyphenyl, 4-chloro-2-methylphenyl, 4-chloro-3-methylphenyl, 2-fluoro-4-cyanophenyl, 2-chloropyridin-5-yl, 5-chloropyridin-2-yl, 3-fluoro-5-chloropyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, 5-fluoropyridin-2-yl, 5-bromopyridin-2-yl, 6-chloropyridazin-3-yl, 5-bromopyrimidin-2-yl, 5-chloropyrimidin-2-yl, 5-fluoropyrimidin-2-yl, 4-chlorothien-2-yl, 5-chlorothien-2-yl, 3-chloropyrazol-1-yl, 4-chloropyrazol-1-yl; and may be present either as a free compound and/or present as an agrochemically acceptable salt thereof.
21. A herbicidal composition which comprises: (i) a compound of formula (I), as defined in claim 1, and (ii) an agrochemically acceptable carrier, diluent and/or solvent; (iii) optionally one or more further herbicides; and (iv) optionally a safener.
22. A method of controlling grassy monocotyledonous weeds in crops of useful plants, comprising applying a compound of formula (I), as defined in claim 1, or a herbicidal composition comprising such a compound, to the weeds, to the plants, or to the locus thereof.
23. The method as claimed in claim 22, wherein the crops of useful plants comprise wheat, barley, rye, triticale, sugarcane, soybean, peanut, pulse crops, cotton, rape, sunflower, linseed, sugarbeet, fodder beet, potato, and/or dicotyledonous vegetables.
24. A compound of formula (II): ##STR00261## wherein: X is methyl or chlorine; R.sup.1AA is methoxy, ethoxy, C.sub.1fluoroalkoxy, ethyl, n-propyl, cyclopropyl or ethynyl; R.sup.4AA is hydrogen, methoxy, ethoxy, C.sub.1fluoroalkoxy or ethyl; and G is hydrogen, an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group; or G is C(O)R.sup.AA or C(O)X.sup.CC R.sup.BB; wherein X.sup.CC is oxygen or sulfur; R.sup.AA is C.sub.1-C.sub.10alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-methyl-, C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.3alkyl; phenyl or phenyl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; monocyclic heteroaryl or monocyclic heteroaryl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; or phenyl-methyl- in which the phenyl is optionally substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; and R.sup.BB is C.sub.1-C.sub.10alkyl, C.sub.2-C.sub.5alkenyl-CH.sub.2, C.sub.2-C.sub.4alkenyl-CH(Me)-, C.sub.2-C.sub.5alkynyl-CH.sub.2, C.sub.2-C.sub.4alkynyl-CH(Me)-, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-methyl-, C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.3alkyl; phenyl or phenyl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; monocyclic heteroaryl or monocyclic heteroaryl substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; or phenyl-methyl- in which the phenyl is optionally substituted by 1 or 2 of, independently, C.sub.1-C.sub.2alkyl, C.sub.1fluoroalkyl, C.sub.1-C.sub.2alkoxy, C.sub.1fluoroalkoxy, fluorine, chlorine or cyano; and wherein the compound of formula (II) is optionally present as an agrochemically acceptable salt thereof.
25. The compound as claimed in claim 24, wherein X is methyl; R.sup.1AA is methoxy, ethyl or n-propyl; R.sup.4AA is hydrogen, methoxy or ethyl; and G is hydrogen, an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group.
Description
PREPARATION EXAMPLES
(1) Those skilled in the art will appreciate that certain compounds described below are -ketoenols (beta-ketoenols), and as such may exist as a single tautomer or as a mixture of keto-enol and diketone tautomers, as described, for example by J. March, Advanced Organic Chemistry, third edition, John Wiley and Sons. The compounds shown below, and in Table T1 herein, are generally drawn as an arbitrary single enol tautomer, but it should be inferred that this description covers both the diketone form and any possible enols which could arise through tautomerism. Where more than one tautomer is observed in proton NMR NMR), the data shown are for the mixture of tautomers. Furthermore, some of the compounds shown below have the possibility of being present in at least two enantiomeric forms; unless drawn as single enantiomers, these compounds will usually be present as a mixture of enantiomers. Additionally, some of the compounds can exist as diastereoisomers, and it should be inferred that these can be present as a mixture of diastereoisomers or as any possible single diastereoisomer. Within the detailed experimental section the diketone tautomer is chosen for naming purposes, even if the predominant tautomer is the enol form.
Typical Abbreviations
(2) DCMdichloromethane DMFN,N-dimethylformamide LDAlithium diisopropylamide THFtetrahydrofuran RTroom temperature (typically ca. 15-30 C. such as ca. 18-25 C.) NMRnuclear magnetic resonance
Intermediate 1Preparation of 3-methoxy-2-(2,4,6-trimethylphenyl)-cyclopent-2-en-1-one (Previously Described as Example 1 Step 1 on Pages 54-55 of WO 2010/000773 A1)
(3) ##STR00036##
(4) To a suspension of 2-bromo-3-methoxy-cyclopent-2-en-1-one (6.75 g, 35.3 mmol), 2,4,6-trimethylphenyl boronic acid (6.99 g, 42.6 mmol) and freshly ground potassium phosphate (15 g, 70.6 mmol) in degassed toluene (180 ml) under nitrogen are added Pd(OAc).sub.2 (159 mg, 0.71 mmol) and S-Phos (2-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl) (579 mg, 1.41 mmol), and the reaction heated to 90 C. with stirring under nitrogen for 4 hours. The reaction mixture is partitioned between ethyl acetate (150 ml) and water (150 ml), and the organic layer is removed, silica gel is added to the organic layer, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 3-methoxy-2-(2,4,6-trimethylphenyl)-cyclopent-2-en-1-one (6.2 g).
Intermediate 2: Preparation of 2-(4-Bromo-2,6-dimethyl-phenyl)-3-methoxy-cyclopent-2-en-1-one
(5) ##STR00037##
Step 1: Preparation of ([4-bromo-2,6-dimethylphenyl]furan-2-yl)methanol (Previously Described in Example 1 Step 1 on Pages 51-52 of WO 2010/089210 A1)
(6) ##STR00038##
(7) 4-Bromo-2,6-dimethyl-1-iodobenzene (5 g, 16 mmol) is dissolved in dry tetrahydrofuran (20 ml) and cooled to 78 C. under an atmosphere of dry nitrogen. Isopropylmagnesium chloride (2M solution in tetrahydrofuran, 10 ml, 20 mmol) is added dropwise with vigorous stirring over 30 minutes. When the addition is complete, the reaction is allowed to warm to room temperature and is stirred for 30 minutes at room temperature. The reaction mixture is cooled to 78 C. and a solution of 2-furaldehyde (2.4 g, 25 mmol) in dry tetrahydrofuran (10 ml) is added dropwise over 30 minutes. Once the addition is complete, the mixture is allowed to warm to room temperature and stirring continued for 2 hours. A solution of saturated aqueous ammonium chloride (30 ml) is added, and the mixture is extracted with dichloromethane (325 ml). The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give ([4-bromo-2,6-dimethylphenyl]furan-2-yl)methanol (3.71 g).
Step 2: Preparation of 5-(4-bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (Previously Described in Example 1 Step 2 on Page 52 of WO 2010/089210 A1)
(8) ##STR00039##
(9) Polyphosphoric acid (500 mg) is added to a warm (55 C.) solution of ([4-bromo-2,6-dimethylphenyl]furan-2-yl)methanol (843 mg, 3 mmol) in acetone (8 ml) and water (2 ml) and the mixture is heated at 55 C. for 24 hours. The mixture is cooled to room temperature and the acetone is removed under reduced pressure. The remaining mixture is partitioned between diethyl ether (20 ml) and water (20 ml). The aqueous phase is extracted with ether (250 ml), and then the organic phases are combined, washed with saturated aqueous sodium bicarbonate solution (20 ml), and brine (20 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 5-(4-bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (596 mg).
Step 3: Preparation of 2-(4-bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (Previously Described in Example 1 Step 3 on Page 52 of WO 2010/089210 A1)
(10) ##STR00040##
(11) To a solution of 5-(4-bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (18.33 g. 65 mmol) in acetone (200 ml) at 0 C. is added, dropwise, a solution of Jones reagent (1.67 M, 39 ml, 65 mmol) and the resulting yellow solution is stirred at 0 C. for 90 minutes. The reaction is quenched by the addition of propan-2-ol (1 ml) and stirred for a further 2 hours. Brine (300 ml) is added and the reaction is extracted with ethyl acetate (3250 ml). The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4-bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (17.2 g).
Step 4: Preparation of 2-(4-Bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione
(12) ##STR00041##
also present as
(13) ##STR00042##
(14) To a solution of 2-(4-bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (50 g, 0.18 mol) in acetic acid (2000 ml) at 25-30 C. is added zinc powder (82.3 g, 1.26 mol). The resulting suspension is heated to 90 C. for 2 hours, followed by cooling to room temperature then filtration through a bed of diatomaceous earth. The residue is washed with methanol (100 ml2) and the solution is concentrated in vacuo. Distilled water is added and the crude product is extracted with ethyl acetate (500 ml3). Organic fractions are combined then washed with distilled water, brine, then dried over sodium sulfate, filtered and the filtrate is concentrated in vacuo to afford 2-(4-bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione. This material is used directly in the next step without further purification.
Step 5: Preparation of 2-(4-Bromo-2,6-dimethyl-phenyl)-3-methoxy-cyclopent-2-en-1-one
(15) ##STR00043##
(16) To a solution of 2-(4-bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione (40 g, 0.143 mol) in acetone (2000 ml) is added anhydrous potassium carbonate (98.5 g, 0.714 mol) and iodomethane (45 ml, 0.72 mol). The resulting mixture is stirred at 25-30 C. for 16 hours, then volatile solvents are removed in vacuo, and the residue is diluted with distilled water (200 ml) and extracted with ethyl acetate (3500 ml). Organic fractions are combined, washed with distilled water, brine, then dried over sodium sulphate, filtered and the filtrate concentrated in vacuo. The crude product is purified by flash column chromatography to afford 2-(4-bromo-2,6-dimethyl-phenyl)-3-methoxy-cyclopent-2-en-1-one.
Intermediate 3: 2-(2,6-diethyl-4-methylphenyl)-3-methoxy-cyclopent-2-en-1-one (Previously Disclosed in Example 2, Pages 54-55 of WO2009/019005A2 (Syngenta Limited))
(17) ##STR00044##
Step 1: Preparation of 2-bromo-3-methoxy-cyclopent-2-en-1-one
(18) ##STR00045##
(19) N-Bromosuccinimide (24.92 g, 0.140 mol) is added, portionwise, over 1 hour to a stirred solution of 3-methoxycyclopent-2-enone (14.95 g, 0.133 mol) in 1,2-dichloroethane (300 ml) at 0 C. in an amber flask. The reaction mixture is stirred at 0 C. for a further 90 minutes and then any remaining solid is removed by filtration. The filtrate is evaporated to dryness under reduced pressure, the resultant solid is dissolved in warm toluene (600 ml) and washed quickly with ice-cold water (2100 ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure until approximately 150 ml remains. The residue is cooled with an ice bath and left for 30 minutes. The resultant solid is removed by filtration, washed with hexane (50 ml) and air-dried to give 2-bromo-3-methoxy-cyclopent-2-en-1-one.
Step 2: Preparation of 2-(2,6-diethyl-4-methylphenyl)-3-methoxy-cyclopent-2-en-1-one
(20) ##STR00046##
(21) To a stirred suspension of 2-bromo-3-methoxy-cyclopent-2-en-1-one (17.5 g, 91.6 mmol), 2,6-diethyl-4-methylphenyl boronic acid (26.4 g, 137 mmol) and freshly powdered potassium phosphate (38.9 g, 183 mmol) in anhydrous, degassed toluene (450 ml) under a nitrogen atmosphere are added palladium (II) acetate (0.411 g, 1.83 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (1.51 g, 3.67 mmol). The reaction mixture is heated at 90 C. for 6.5 hours and then allowed to cool to room temperature overnight. The reaction is diluted with water (400 ml) and extracted with ethyl acetate (3150 ml). The combined organic extracts are washed with brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-3-methoxy-cyclopent-2-en-1-one.
Example 1: Preparation of 2-[4-(5-chloropyrimidin-2-yl)-2,6-dimethylphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(22) ##STR00047##
Step 1: Preparation of 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one
(23) ##STR00048##
(24) To a mixture of 2-(4-bromo-2,6-dimethylphenyl)-3-methoxycyclopent-2-en-1-one (described in WO 2011073060) (10.0 g, 33.9 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (13.0 g, 50.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.24 g, 1.36 mmol), potassium acetate (4.99 g, 50.8 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (2.29 g, 5.42 mmol) under nitrogen was added anhydrous 1,4-dioxane (150 ml). The resulting mixture was heated at 80 C. for 3 hour 15 minutes, then cooled to room temperature and poured into distilled water (150 ml). After dilution with ethyl acetate (150 ml) the phases were separated and the aqueous phase was extracted with further ethyl acetate (120 ml). The combined organic phases were washed with distilled water, brine, dried over anhydrous magnesium sulphate, filtered through diatomaceous earth and concentrated in vacuo. The crude product was triturated with isohexane to afford 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one.
Step 2: Preparation of 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one
(25) ##STR00049##
(26) To a solution of 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one (0.50 g, 1.46 mmol) in anhydrous tetrahydrofuran (10 ml) under nitrogen at 78 C. was added a solution of lithium diisopropylamide (1.30 ml, 2.34 mmol, 1.8M solution in a mixture of tetrahydrofuran, heptane and ethylbenzene) dropwise. The solution was stirred at 78 C. for 45 minutes, after which a second solution of 3-bromoprop-1-yne (0.195 ml, 1.75 mmol, 80 wt % in toluene) in tetrahydrofuran (1 ml) was added dropwise. The reaction was stirred at 78 C. for a further 1 hour then allowed to warm to room temperature overnight. The reaction mixture was quenched with aqueous ammonium chloride (10 ml) then further diluted with ethyl acetate (10 ml) and distilled water (2 ml). The phases were separated and the aqueous phase was additionally extracted with ethyl acetate (2). The combined organic phases were washed with brine, dried over magnesium sulphate and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one as a pale yellow solid.
Step 3: Preparation of 2-[4-(5-chloropyrimidin-2-yl)-2,6-dimethylphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one
(27) ##STR00050##
(28) To a mixture of 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one (0.225 g, 0.59 mmol), 2-bromo-5-chloro-pyrimidine (0.17 g, 0.88 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.014 g, 0.012 mmol) under nitrogen was added 1,2-dimethoxyethane (4 ml) followed by stirring at room temperature for 30 minutes. After this time an aqueous solution of potassium carbonate (0.165 g, 1.183 mmol) in water (1.0 ml) was added and the mixture was heated at 130 C. for 40 minutes under microwave irradiation. The reaction mixture was poured into distilled water and diluted with ethyl acetate. The phases were separated and the aqueous phase was extracted with ethyl acetate (2). The combined organic phases were dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to afford crude 2-[4-(5-chloropyrimidin-2-yl)-2,6-dimethylphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one.
Step 4: Preparation of 2-[4-(5-chloropyrimidin-2-yl)-2,6-dimethylphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(29) ##STR00051##
(30) To a solution of 2-[4-(5-chloropyrimidin-2-yl)-2,6-dimethylphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one (414 mg, 1.13 mmol) in acetone (3 ml) was added 2M aqueous hydrochloric acid (2 ml). The mixture was heated at 80 C. for 30 minutes under microwave irradiation then left to stand at room temperature overnight. The reaction mixture was diluted in dichloromethane and distilled water, then filtered through diatomaceous earth followed by further washing with dichloromethane. The phases were separated and the organic phase was concentrated in vacuo to afford a crude product which was purified by preparative reverse phase HPLC to afford 2-[4-(5-chloropyrimidin-2-yl)-2,6-dimethylphenyl]-4-prop-2-ynylcyclopentane-1,3-dione.
Example 2: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(31) ##STR00052##
Step 1: Preparation of 2-[2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one
(32) ##STR00053##
(33) To a mixture of 2-(2-chloro-6-methoxyphenyl)-3-methoxycyclopent-2-en-1-one (2.87 g, 11.4 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (3.46 g, 13.6 mmol), (1,5-cyclooctadiene)(methoxy)iridium(I) dimer (0.339 g, 0.511 mmol) and 4,4-di-tert-butyl bipyridine (0.280 g, 1.02 mmol) under nitrogen was added tert-butyl methyl ether (12 ml). The resulting solution was heated to 80 C. for 5 hours, then allowed to stand at room temperature overnight. The reaction mixture was concentrated in vacuo then purified by flash column chromatography on silica to afford 2-[2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one.
Step 2: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-3-methoxy-cyclopent-2-en-1-one
(34) ##STR00054##
(35) To a mixture of 2-[2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one (0.25 g, 0.66 mmol), 1-bromo-4-chlorobenzene (0.19 g, 0.99 mmol) and 1,1-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane (0.055 g, 0.066 mmol) under nitrogen was added degassed dimethoxyethane (2.5 ml) followed by a solution of tripotassium phosphate (1.40 ml, 2.64 mmol, 40% solution in distilled water). The reaction mixture was heated at 85 C. for 3 hours then left to stand at room temperature overnight. The reaction mixture was poured into distilled water, diluted with ethyl acetate and acidified with 2M aqueous hydrochloric acid. The reaction mixture was filtered through diatomaceous earth (washing with more ethyl acetate), the phases were separated and the organic phase was concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-3-methoxycyclopent-2-en-1-one.
Step 3: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one
(36) ##STR00055##
(37) To a solution of 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-3-methoxy-cyclopent-2-en-1-one (0.117 g, 0.322 mmol) in anhydrous tetrahydrofuran (3 ml) under nitrogen at 78 C. was added potassium bis(trimethylsilyl)amide (0.38 ml, 0.38 mmol, 1M solution in tetrahydrofuran) dropwise, and the reaction was allowed to stir at this temperature for 65 minutes. A solution of 3-bromoprop-1-yne (0.043, 0.39 mmol, 80 wt % in toluene) in anhydrous tetrahydrofuran (1 ml) was then added dropwise to the reaction mixture, followed by stirring at 78 C. for 30 minutes then at room temperature for 18 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 ml) and diluted with ethyl acetate (10 ml). Distilled water (5 ml) was added and the phases were separated. The aqueous phase was extracted with further ethyl acetate and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to afford 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one. This material was used directly in the next step.
Step 4: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(38) ##STR00056##
(39) A solution of 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one (0.115 g, 0.29 mmol) in acetone (2.0 ml) and 2M aqueous hydrochloric acid (1.0 ml) was heated at 100 C. for 30 minutes under microwave irradiation. The reaction mixture was poured into a mixture of dichloromethane and distilled water and the phases were separated. The organic phase was concentrated in vacuo and purified by preparative reverse phase HPLC to afford 2-[2-chloro-4-(4-chlorophenyl)-6-methoxyphenyl]-4-prop-2-ynylcyclopentane-1,3-dione as a white solid.
Example 3: Preparation of 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(40) ##STR00057##
Step 1: Preparation of 2-[4-(4-fluorophenyl)-2-fluoro-6-methoxyphenyl]-3-methoxycyclopent-2-en-1-one
(41) ##STR00058##
(42) To a mixture of 2-(4-bromo-2-fluoro-6-methoxyphenyl)-3-methoxycyclopent-2-en-1-one (0.38 g, 1.22 mmol), 4-fluorophenylboronic acid (0.254 g, 1.82 mmol) and 1,1-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane (0.10 g, 0.12 mmol) under nitrogen was added degassed dimethoxyethane (4.2 ml) followed by a solution of tripotassium phosphate (1.03 ml, 4.85 mmol, 40% solution in distilled water). The reaction mixture was heated to 85 C. for 3 hours then left to stand at room temperature overnight. The reaction mixture was diluted with dichloromethane and distilled water and filtered through diatomaceous earth. The phases were separated and the organic phase was concentrated in vacuo and purified by flash column chromatography on silica to afford 2-[4-(4-fluorophenyl)-2-fluoro-6-methoxyphenyl]-3-methoxycyclopent-2-en-1-one.
Step 2: Preparation of 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one
(43) ##STR00059##
(44) To a solution of 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-3-methoxycyclopent-2-en-1-one (0.30 g, 0.91 mmol) in anhydrous tetrahydrofuran (8 ml) under nitrogen at 78 C. was added potassium bis(trimethylsilyl)amide (1.09 mL, 1.09 mmol, 1M solution in tetrahydrofuran) dropwise, and the reaction was stirred at this temperature for 2 hours. A solution of 3-bromoprop-1-yne (0.121 ml, 1.09 mmol, 80 wt % in toluene) in anhydrous tetrahydrofuran (1 ml) was added dropwise to the reaction mixture, followed by stirring at 78 C. for 15 minutes and at room temperature for 18 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 ml), diluted with ethyl acetate (10 ml) and the phases were separated. The aqueous phase was extracted with further ethyl acetate (2), and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one.
Step 3: Preparation of 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(45) ##STR00060##
(46) A solution of 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one (0.230 g, 0.62 mmol) in acetone (2.0 ml) and 2M aqueous hydrochloric acid (1.0 ml) was heated at 100 C. for 30 minutes under microwave irradiation, then left to stand at room temperature overnight. The reaction mixture was poured into a mixture of dichloromethane and distilled water and the phases were separated. The crude product was extracted into 0.5M aqueous potassium carbonate (20 ml) and the aqueous phase was washed with dichloromethane (3). The aqueous phase was acidified to pH1 with concentrated hydrochloric acid, and the resulting white solid was filtered, washed with additional distilled water and air dried. The product was further dried under vacuum at 55 C. for 18 hours to afford 2-[2-fluoro-4-(4-fluorophenyl)-6-methoxyphenyl]-4-prop-2-ynylcyclopentane-1,3-dione.
Example 4: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(47) ##STR00061##
Step 1: Preparation of 2-[2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one
(48) ##STR00062##
(49) To a mixture of 2-(2-chloro-6-fluorophenyl)-3-methoxycyclopent-2-en-1-one (5.0 g, 20.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (6.33 g, 24.9 mmol), (1,5-cyclooctadiene)(methoxy)iridium(I) dimer (0.62 g, 0.93 mmol) and 4-tert-butyl-2-(4-tert-butyl-2-pyridyl)pyridine (0.50 g, 1.87 mmol) under nitrogen was added tert-butyl methyl ether (21 ml). The resulting solution was heated at 80 C. for 5 hours, cooled to room temperature and concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-[2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one as a yellow solid.
Step 2: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-3-methoxycyclopent-2-en-1-one
(50) ##STR00063##
(51) To a mixture of 2-[2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methoxycyclopent-2-en-1-one (0.50 g, 1.06 mmol), 1,1-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane (0.09 g, 0.11 mmol) and 1-bromo-4-chlorobenzene (0.31 g, 1.60 mmol) was added 1,2-dimethoxyethane (8 ml) followed by tripotassium phosphate (0.36 g, 1.70 mmol) in distilled water (0.54 ml). The reaction mixture was heated at 160 C. for 30 minutes under microwave irradiation, followed by cooling to room temperature and subsequent dilution with dichloromethane and distilled water. After filtering through diatomaceous earth the phases were separated and the aqueous phase was further washed with dichloromethane. The organic phases were combined and concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-3-methoxycyclopent-2-en-1-one as a brown gum.
Step 3: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one
(52) ##STR00064##
(53) To a solution of 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-3-methoxycyclopent-2-en-1-one (0.28 g, 0.69 mmol) in anhydrous tetrahydrofuran (4 ml) under nitrogen at 78 C. was added potassium bis(trimethylsilyl)amide (0.83 ml, 0.83 mmol, 1M solution in tetrahydrofuran) dropwise, and the reaction mixture was stirred at this temperature for 45 minutes. To this solution was added a second solution of 3-bromoprop-1-yne (0.093 ml, 0.83 mmol, 80 wt % in toluene) in anhydrous tetrahydrofuran (1 ml), followed by stirring at 78 C. for 40 minutes then at room temperature for 18 hours. The reaction mixture was quenched with aqueous ammonium chloride (10 ml) and further diluted with ethyl acetate (10 ml). Distilled water (1 ml) was added, the phases separated, and the aqueous phase extracted again with ethyl acetate (2). The organic phases were combined, washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash column chromatography on silica afforded 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one.
Step 4: Preparation of 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(54) ##STR00065##
(55) To a solution of 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one (0.19 g, 0.48 mmol) in acetone (2.5 ml) was added 2M aqueous hydrochloric acid (0.5 ml) and the resulting solution was heated at 100 C. for 30 minutes under microwave irradiation. The reaction mixture was diluted with dichloromethane and distilled water and the phases were separated. The aqueous phase was washed with further dichloromethane, and the combined organic phases were concentrated in vacuo to afford 2-[2-chloro-4-(4-chlorophenyl)-6-fluorophenyl]-4-prop-2-ynylcyclopentane-1,3-dione as a beige solid.
Example 5: Preparation of 2-[5-(4-chlorophenyl)-2-methylphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(56) ##STR00066##
Step 1: Preparation of (5-bromo-2-methylphenyl)-(2-furyl)methanol
(57) ##STR00067##
(58) To a solution of 4-bromo-1-iodo-2-methylbenzene (2.0 g, 6.74 mmol) in anhydrous tetrahydrofuran (10 ml) under nitrogen at 30 C. was added isopropylmagnesium chloride lithium chloride complex (5.44 ml, 7.07 mmol, 1.3M solution in tetrahydrofuran) dropwise, maintaining a temperature below 20 C. Once the addition was complete the reaction was allowed to warm to room temperature and stir for 1.5 hours. Additional isopropylmagnesium chloride lithium chloride complex (2.5 ml, 3.25 mmol, 1.3M solution in tetrahydrofuran) was added and the reaction mixture was stirred at 10 C. for 90 mins. A solution of furan-2-carbaldehyde (0.71 g, 7.40 mmol) in tetrahydrofuran (2 ml) was added dropwise, maintaining a reaction temperature below 15 C. The solution was stirred for an additional 60 minutes at 15 C., then at room temperature for 1.5 hours. The reaction mixture was quenched with aqueous ammonium chloride and the crude product extracted with ethyl acetate. The organic phases were combined, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash column chromatography on silica afforded (5-bromo-2-methylphenyl)-(2-furyl)methanol as a yellow gum.
Step 2: Preparation of 2-(5-bromo-2-methylphenyl)-3-methoxycyclopent-2-en-1-one
(59) ##STR00068##
(60) To a solution of (5-bromo-2-methylphenyl)-(2-furyl)methanol (0.97 g, 3.64 mmol) in N,N-dimethylacetamide (9.7 ml) was added 4-methylbenzenesulfonic acid (0.32 g, 1.82 mmol), and the reaction mixture was heated at 170 C. for 2.5 hours. After cooling to room temperature iodomethane (0.77 g, 5.46 mmol) was added followed by potassium carbonate (1.01 g, 7.28 mmol). The reaction mixture was stirred at room temperature for 3 hours then quenched with 2M aqueous hydrochloric acid. The crude product was extracted with ethyl acetate, and the organic phase was further washed with 2M aqueous hydrochloric acid. The organic phases were combined, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-(5-bromo-2-methylphenyl)-3-methoxycyclopent-2-en-1-one as a brown oil.
Step 3: Preparation of 2-[5-(4-chlorophenyl)-2-methylphenyl]-3-methoxycyclopent-2-en-1-one
(61) ##STR00069##
(62) To a solution of 2-(5-bromo-2-methylphenyl)-3-methoxycyclopent-2-en-1-one (0.53 g, 1.88 mmol) in 1,2-dimethoxyethane (10 ml) was added 4-chlorophenylboronic acid (0.35 g, 2.25 mmol) and a solution of tripotassium phosphate (1.59 g, 7.51 mmol) in distilled water (2.90 ml). After degassing with nitrogen for 5 minutes [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.31 g, 0.37 mmol) was added in one portion and the mixture was heated at 120 C. for 45 minutes under microwave irradiation. The reaction mixture was diluted with distilled water and ethyl acetate. The phases were separated and the aqueous phase was further extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica to afford 2-[5-(4-chlorophenyl)-2-methylphenyl]-3-methoxycyclopent-2-en-1-one as an orange gum.
Step 4: Preparation of 2-[5-(4-chlorophenyl)-2-methylphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one
(63) ##STR00070##
(64) To a solution of 2-[5-(4-chlorophenyl)-2-methylphenyl]-3-methoxycyclopent-2-en-1-one (0.20 g, 0.64 mmol) in anhydrous tetrahydrofuran (4 ml) at 70 C. under nitrogen was added potassium bis(trimethylsilyl)amide (0.88 ml, 0.803 mmol, 0.91M in tetrahydrofuran) dropwise, maintaining a temperature below 60 C. Once addition was complete the reaction mixture was stirred at 70 C. for 60 minutes, followed by addition of propargyl bromide (0.090 ml, 0.803 mmol, 80% solution in toluene). The reaction mixture was stirred at 70 C. for 90 minutes, then additional potassium bis(trimethylsilyl)amide (0.88 ml, 0.803 mmol, 0.91M in tetrahydrofuran) was added dropwise. After stirring at 70 C. for 1 hour the solution was warmed to 40 C. and stirred for an additional 1 hour. The reaction mixture was warmed to 10 C. at which stage it was quenched with 2M aqueous hydrochloric acid. The organic phases were combined, concentrated in vacuo and purified by flash column chromatography on silica to afford 2-[5-(4-chlorophenyl)-2-methylphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one. This material was used directly in the next step.
Step 5: Preparation of 2-[5-(4-chlorophenyl)-2-methylphenyl]-4-prop-2-ynylcyclopentane-1,3-dione
(65) ##STR00071##
(66) A solution of 2-[5-(4-chlorophenyl)-2-methylphenyl]-3-methoxy-5-prop-2-ynylcyclopent-2-en-1-one (0.06 g, 0.17 mmol) in a mixture of 2M aqueous hydrochloric acid (1 ml) and acetone (1 ml) was heated at 60 C. for 4 hours. After standing at room temperature for 2 days the reaction mixture was diluted with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash column chromatography on silica afforded 2-[5-(4-chlorophenyl)-2-methylphenyl]-4-prop-2-ynylcyclopentane-1,3-dione.
Example 6: Synthesis of 2-(2,6-diethyl-4-methyl-phenyl)-4-(prop-2-ynyl)-cyclopentane-1,3-dione (Compound A-25)
(67) ##STR00072##
Step One: Alkylation of Enol Ether to Prepare 2-(2,6-diethyl-4-methyl-phenyl)-3-methoxy-5-(prop-2-ynyl)-cyclopent-2-en-1-one
(68) ##STR00073##
(69) To a solution of 2-(2,6-diethyl-4-methyl-phenyl)-3-methoxy-cyclopent-2-en-1-one (499 mg, 1.93 mmol, which can e.g. be prepared as described in Intermediate 3) in anhydrous tetrahydrofuran (10 ml) at 78 C. under a nitrogen atmosphere was added dropwise lithium diisopropylamide (LDA) (1.2 ml of a 1.8M solution in tetrahydrofuran, 2.2 mmol). The reaction was stirred for 30 minutes at 78 C. and then a solution of propargyl bromide (373 mg of an 80% w/w solution in toluene, 2.2 mmol) in 2 ml of tetrahydrofuran was added in a single portion. The reaction was stirred at 78 C. for a further 30 minutes and then allowed to warm to room temperature and stirred for a further hour. The reaction was quenched with saturated aqueous NH.sub.4Cl solution (20 ml) and extracted with EtOAc (225 ml). The combined organic extracts were evaporated to dryness under reduced pressure and the crude product purified by flash chromatography over SiO.sub.2 using an EtOAc/hexane gradient as eluent to give the desired product (500 mg, 87%). .sup.1H NMR (400 MHz, CDCl.sub.3) 6.90 (2H, s), 3.78 (3H, s), 3.00 (1H, dd), 2.80-2.65 (4H, m), 2.45-2.35 (4H, m), 2.30 (3H, s), 1.95 (1H, s), 1.15-1.00 (6H, m).
Step 2: Enol Ether Cleavage to Prepare 2-(2,6-diethyl-4-methyl-phenyl)-4-(prop-2-ynyl)-cyclopentane-1,3-dione
(70) ##STR00074##
(71) To a solution of 2-(2,6-diethyl-4-methyl-phenyl)-3-methoxy-5-(prop-2-ynyl)-cyclopent-2-en-1-one (250 mg, 0.84 mmol) in acetone (10 ml) was added 2M aqueous hydrochloric acid (10 ml). The reaction was heated at reflux for 3 hours and then allowed to cool to room temperature. The pH of the reaction mixture was adjusted to about 1 by addition of further 2M aqueous hydrochloric acid, and then the reaction mixture was extracted with EtOAc (250 ml). The combined organic extracts were evaporated to dryness under reduced pressure and purified by flash chromatography over SiO.sub.2 using an EtOAc/hexane gradient as eluent to give the desired product (210 mg, 89%). .sup.1H NMR (400 MHz, CDCl.sub.3) 6.90 (2H, s), 2.82-2.78 (1H, m), 2.65 (1H, dd), 2.60-2.50 (3H, m), 2.40-2.25 (7H, m), 1.95 (1H, s), 1.10-1.00 (6H, m).
Example 7: Chiral HPLC Separation of Enantiomers of Compound XXX
(72) In one optional embodiment of the invention, any specific compound of the invention (named compound XXX) (racemic) is separated into the two corresponding enantiomerically pure (or substantially enantiomerically pure) compounds using a chiral HPLC column. In one optional example, the chiral HPLC uses the following method and the following conditions.
(73) Chiral HPLC column: a (s,$) WhelkO1-5 micron-21 mm250 mm HPLC column, manufactured by Regis Technologies, Inc. In this column, the chiral stationary phase is (S,S) 1-(3-5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene.
(74) The solvent system to be used as an eluent for the column varies depending on the racemic compound to be separated into enantiomers, but one example of a solvent system is: a 30:70 (by volume) mixture of Solvent A and Solvent B, in which: Solvent A is isohexane containing 0.1% v/v of trifluoroacetic acid (TFA), and Solvent B is ethanol.
(75) Other conditions (these are sample conditions only and may vary widely):
(76) Flow rate through column: about 21 ml/minute. Run time: about 20 minutes.
(77) Loading (compound loaded onto column): about 50 mg/ml of compound in ethanol.
(78) Volume of sample (compound) injected per run=about 1800 microliters.
(79) Number of injections of compound=about 5.
(80) Amount of racemic compound XXX used: (for example) about 300-400 mg
(81) Abbreviation: HPLC=high performance (or high pressure) liquid chromatography.
(82) General Note on Chiral HPLC Separation of Enantiomers:
(83) In one optional embodiment, the above procedure using chiral HPLC is used to separate the enantiomers of other compounds of formula (I) of the present the invention. Chiral columns which might be useful to achieve this are as follows:
(84) (s,$) WhelkO1-5 micron-21 mm250 mm HPLC column, manufactured by Regis Technologies, Inc [in this column, the chiral stationary phase is (S,S) 1-(3-5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene];
(85) Kromasil AmyCoat [whose chiral stationary phase is tris-(3,5-dimethylphenyl)carbamoyl amylose];
(86) Kromasil CelluCoat [whose chiral stationary phase is tris-(3,5-dimethylphenyl)carbamoyl cellulose];
(87) Chiralpak IA [whose chiral stationary phase is a (3,5-dimethylphenyl)carbamate derivative of amylose];
(88) Chiralpak IB [whose chiral stationary phase is tris-(3,5-dimethylphenyl)carbamate derivative of cellulose];
(89) Chiralpak IC [whose chiral stationary phase is cellulose tris(3,5-dichlorophenyl)carbamate];
(90) Lux Amylose-2 [whose chiral stationary phase is amylose tris(5-chloro-2-methylphenylcarbamate)]; or
(91) Lux Cellulose-2 [whose chiral stationary phase is Cellulose tris(3-chloro-4-methylphenylcarbamate)].
Example 8 Preparation of [2-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-3-oxo-4-prop-2-ynyl-cyclopentyl]acetate
(92) ##STR00075##
(93) To a cooled (0 C.) suspension of 2-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-4-prop-2-ynylcyclopentane-1,3-dione (0.203 g) in dichloromethane (15 mL) was added triethylamine (0.127 mL) followed by acetyl chloride (0.06475 mL). The solution was stirred cold for 15 minutes then allowed to warm to room temperature and the reaction mixture was stirred at room temperature for 75 min.
(94) The reaction was partitioned between water and dichloromethane and the organic layer was concentrated and purified by chromatography on silica eluting with ethyl acetate in isohexane to give [2-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-3-oxo-4-prop-2-ynyl-cyclopentyl]acetate (105 mg) as a yellow gum.
(95) .sup.1H NMR (500 MHz, CDCl.sub.3) =7.56-7.52 (m, 2H), 7.24 (s, 2H), 7.13-7.09 (m, 2H), 3.36-3.29 (m, 1H), 3.10 (dd, 1H), 2.94-2.92 (m, 1H), 2.73-2.71 (m, 2H), 2.18-2.17 (m, 9H), 2.00 (t, 1H)
(96) (Note: The other isomer, in which the acetyloxy group is attached to the ring carbon adjacent to the prop-2-ynyl group, might be formed, as well or instead.)
(97) Additional compounds in Table T1 below illustrate the present invention, and are particular embodiments of the compounds of formula (I) according to the present invention. For the most part, these compounds can generally be prepared by methods similar to those shown in the Examples and/or in the process section hereinabove using appropriate starting materials.
(98) TABLE-US-00010 TABLE T1 It should be noted that certain compounds of the invention may exist as a mixture of isomers, including sometimes atropisomers, e.g. as noted above, under the conditions used to obtain the .sup.1H NMR data. Where this has occurred, the characterising data are reported for all isomers present at ambient temperature in the specified solvent. Unless otherwise stated, proton (.sup.1H) NMR spectra disclosed herein were recorded at ambient temperature. Compound .sup.1H NMR (CDCl.sub.3 unless stated, Number Structure usually 400 MHz) data A1
(99) The compounds of the following Tables 1 to 60 can be obtained in an analogous manner.
(100) Table 1 covers compounds of the following type
(101) ##STR00121##
(102) wherein R.sup.1 is methyl, R.sup.4 is methyl, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(103) TABLE-US-00011 TABLE 1 Compound Number R.sup.2 1.001 phenyl 1.002 3-fluorophenyl 1.003 4-fluorophenyl 1.004 3-chlorophenyl 1.005 4-chlorophenyl 1.006 3-bromophenyl 1.007 4-bromophenyl 1.008 4-iodophenyl 1.009 4-methylphenyl 1.010 4-cyanophenyl 1.011 4-methoxyphenyl 1.012 3-difluoromethoxyphenyl 1.013 4-difluoromethoxyphenyl 1.014 3-difluoromethylphenyl 1.015 4-difluoromethylphenyl 1.016 3-trifluoromethylphenyl 1.017 4-trifluoromethylphenyl 1.018 3-trifluoromethoxyphenyl 1.019 4-trifluoromethoxyphenyl 1.020 4-methylthiophenyl 1.021 4-methylsulfinylphenyl 1.022 4-methylsulfonylphenyl 1.023 2,4-difluorophenyl 1.024 3,4-difluorophenyl 1.025 3,5-difluorophenyl 1.026 2,4-dichlorophenyl 1.027 3,4-dichlorophenyl 1.028 4-chloro-2-fluorophenyl 1.029 4-chloro-3-fluorophenyl 1.030 4-chloro-2-methoxyphenyl 1.031 4-chloro-3-methoxyphenyl 1.032 4-chloro-2-methylphenyl 1.033 4-chloro-3-methylphenyl 1.034 2-fluoro-4-cyanophenyl 1.035 2-chloropyridin-5-yl 1.036 5-chloropyridin-2-yl 1.037 3-fluoro-5-chloropyridin-2-yl 1.038 5-trifluoromethylpyridin-2-yl 1.039 3-chloro-5-trifluoromethylpyridin-2-yl 1.040 5-fluoropyridin-2-yl 1.041 5-bromopyridin-2-yl 1.042 6-chloropyridazin-3-yl 1.043 5-bromopyrimidin-2-yl 1.044 5-chloropyrimidin-2-yl 1.045 5-fluoropyrimidin-2-yl 1.046 4-chlorothien-2-yl 1.047 5-chlorothien-2-yl 1.048 3-chloropyrazol-1-yl 1.049 4-chloropyrazol-1-yl
(104) Table 2 covers compounds of the following type
(105) ##STR00122##
(106) wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(107) Table 3 covers compounds of the following type
(108) ##STR00123##
(109) wherein R.sup.1 is methyl, R.sup.4 is ethyl, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(110) Table 4 covers compounds of the following type
(111) ##STR00124##
(112) wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(113) Table 5 covers compounds of the following type
(114) ##STR00125##
(115) wherein R.sup.1 is methyl, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(116) Table 6 covers compounds of the following type
(117) ##STR00126##
(118) wherein R.sup.1 is methyl, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(119) Table 7 covers compounds of the following type
(120) ##STR00127##
(121) wherein R.sup.1 is methyl, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(122) Table 8 covers compounds of the following type
(123) ##STR00128##
(124) wherein R.sup.1 is methyl, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(125) Table 9 covers compounds of the following type
(126) ##STR00129##
(127) wherein R.sup.1 is chloro, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(128) Table 10 covers compounds of the following type
(129) ##STR00130##
(130) wherein R.sup.1 is chloro, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(131) Table 11 covers compounds of the following type
(132) ##STR00131##
(133) wherein R.sup.1 is chloro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(134) Table 12 covers compounds of the following type
(135) ##STR00132##
(136) wherein R.sup.1 is chloro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(137) Table 13 covers compounds of the following type
(138) ##STR00133##
(139) wherein R.sup.1 is fluoro, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(140) Table 14 covers compounds of the following type
(141) ##STR00134##
(142) wherein R.sup.1 is fluoro, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(143) Table 15 covers compounds of the following type
(144) ##STR00135##
(145) wherein R.sup.1 is fluoro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(146) Table 16 covers compounds of the following type
(147) ##STR00136##
(148) wherein R.sup.1 is fluoro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(149) Table 17 covers compounds of the following type
(150) ##STR00137##
(151) wherein R.sup.1 is bromo, R.sup.4 is methoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(152) Table 18 covers compounds of the following type
(153) ##STR00138##
(154) wherein R.sup.1 is bromo, R.sup.4 is ethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(155) Table 19 covers compounds of the following type
(156) ##STR00139##
(157) wherein R.sup.1 is bromo, R.sup.4 is 2-methoxyethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(158) Table 20 covers compounds of the following type
(159) ##STR00140##
(160) wherein R.sup.1 is bromo, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(161) Table 21 covers compounds of the following type
(162) ##STR00141##
(163) wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(164) Table 22 covers compounds of the following type
(165) ##STR00142##
(166) wherein R.sup.1 is chloro, R.sup.4 is chloro, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(167) Table 23 covers compounds of the following type
(168) ##STR00143##
(169) wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(170) Table 24 covers compounds of the following type
(171) ##STR00144##
(172) wherein R.sup.1 is bromo, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(173) Table 25 covers compounds of the following type
(174) ##STR00145##
(175) wherein R.sup.1 is fluoro, R.sup.4 is fluoro, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(176) Table 26 covers compounds of the following type
(177) ##STR00146##
(178) wherein R.sup.1 is fluoro, R.sup.4 is chloro, R.sup.10 is hydrogen and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(179) Table 27 covers compounds of the following type
(180) ##STR00147##
(181) wherein R.sup.1 is methyl, R.sup.4 is methyl, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(182) Table 28 covers compounds of the following type
(183) ##STR00148##
(184) wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(185) Table 29 covers compounds of the following type
(186) ##STR00149##
(187) wherein R.sup.1 is methyl, R.sup.4 is ethyl, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(188) Table 30 covers compounds of the following type
(189) ##STR00150##
(190) wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(191) Table 31 covers compounds of the following type
(192) ##STR00151##
(193) wherein R.sup.1 is methyl, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(194) Table 32 covers compounds of the following type
(195) ##STR00152##
(196) wherein R.sup.1 is methyl, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(197) Table 33 covers compounds of the following type
(198) ##STR00153##
(199) wherein R.sup.1 is methyl, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(200) Table 34 covers compounds of the following type
(201) ##STR00154##
(202) wherein R.sup.1 is methyl, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(203) Table 35 covers compounds of the following type
(204) ##STR00155##
(205) wherein R.sup.1 is chloro, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(206) Table 36 covers compounds of the following type
(207) ##STR00156##
(208) wherein R.sup.1 is chloro, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(209) Table 37 covers compounds of the following type
(210) ##STR00157##
(211) wherein R.sup.1 is chloro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(212) Table 38 covers compounds of the following type
(213) ##STR00158##
(214) wherein R.sup.1 is chloro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(215) Table 39 covers compounds of the following type
(216) ##STR00159##
(217) wherein R.sup.1 is fluoro, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(218) Table 40 covers compounds of the following type
(219) ##STR00160##
(220) wherein R.sup.1 is fluoro, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(221) Table 41 covers compounds of the following type
(222) ##STR00161##
(223) wherein R.sup.1 is fluoro, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(224) Table 42 covers compounds of the following type
(225) ##STR00162##
(226) wherein R.sup.1 is fluoro, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(227) Table 43 covers compounds of the following type
(228) ##STR00163##
(229) wherein R.sup.1 is bromo, R.sup.4 is methoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(230) Table 44 covers compounds of the following type
(231) ##STR00164##
(232) wherein R.sup.1 is bromo, R.sup.4 is ethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(233) Table 45 covers compounds of the following type
(234) ##STR00165##
(235) wherein R.sup.1 is bromo, R.sup.4 is 2-methoxyethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(236) Table 46 covers compounds of the following type
(237) ##STR00166##
(238) wherein R.sup.1 is bromo, R.sup.4 is 2,2,2-trifluoroethoxy, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(239) Table 47 covers compounds of the following type
(240) ##STR00167##
(241) wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(242) Table 48 covers compounds of the following type
(243) ##STR00168##
(244) wherein R.sup.1 is chloro, R.sup.4 is chloro, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(245) Table 49 covers compounds of the following type
(246) ##STR00169##
(247) wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(248) Table 50 covers compounds of the following type
(249) ##STR00170##
(250) wherein R.sup.1 is bromo, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(251) Table 51 covers compounds of the following type
(252) ##STR00171##
(253) wherein R.sup.1 is fluoro, R.sup.4 is fluoro, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(254) Table 52 covers compounds of the following type
(255) ##STR00172##
(256) wherein R.sup.1 is fluoro, R.sup.4 is chloro, R.sup.10 is methyl and all of R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.2 is as defined in Table 1.
(257) Table 53 covers compounds of the following type
(258) ##STR00173##
(259) wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53 below.
(260) TABLE-US-00012 TABLE 53 Compound Number R.sup.3 53.001 phenyl 53.002 3-fluorophenyl 53.003 4-fluorophenyl 53.004 3-chlorophenyl 53.005 4-chlorophenyl 53.006 3-bromophenyl 53.007 4-bromophenyl 53.008 4-iodophenyl 53.009 4-methylphenyl 53.010 4-cyanophenyl 53.011 4-methoxyphenyl 53.012 3-difluoromethoxyphenyl 53.013 4-difluoromethoxyphenyl 53.014 3-difluoromethylphenyl 53.015 4-difluoromethylphenyl 53.016 3-trifluoromethylphenyl 53.017 4-trifluoromethylphenyl 53.018 3-trifluoromethoxyphenyl 53.019 4-trifluoromethoxyphenyl 53.020 4-methylthiophenyl 53.021 4-methylsulfinylphenyl 53.022 4-methylsulfonylphenyl 53.023 2,4-difluorophenyl 53.024 3,4-difluorophenyl 53.025 3,5-difluorophenyl 53.026 2,4-dichlorophenyl 53.027 3,4-dichlorophenyl 53.028 4-chloro-2-fluorophenyl 53.029 4-chloro-3-fluorophenyl 53.030 4-chloro-2-methoxyphenyl 53.031 4-chloro-3-methoxyphenyl 53.032 4-chloro-2-methylphenyl 53.033 4-chloro-3-methylphenyl 53.034 2-fluoro-4-cyanophenyl 53.035 2-chloropyridin-5-yl 53.036 5-chloropyridin-2-yl 53.037 3-fluoro-5-chloropyridin-2-yl 53.038 5-trifluoromethylpyridin-2-yl 53.039 3-chloro-5-trifluoromethylpyridin-2-yl 53.040 5-fluoropyridin-2-yl 53.041 5-bromopyridin-2-yl 53.042 6-chloropyridazin-3-yl 53.043 5-bromopyrimidin-2-yl 53.044 5-chloropyrimidin-2-yl 53.045 5-fluoropyrimidin-2-yl 53.046 4-chlorothien-2-yl 53.047 5-chlorothien-2-yl 53.048 3-chloropyrazol-1-yl 53.049 4-chloropyrazol-1-yl
(261) Table 54 covers compounds of the following type
(262) ##STR00174##
(263) wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
(264) Table 55 covers compounds of the following type
(265) ##STR00175##
(266) wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
(267) Table 56 covers compounds of the following type
(268) ##STR00176##
(269) wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is hydrogen and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
(270) Table 57 covers compounds of the following type
(271) ##STR00177##
(272) wherein R.sup.1 is methyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
(273) Table 58 covers compounds of the following type
(274) ##STR00178##
(275) wherein R.sup.1 is ethyl, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
(276) Table 59 covers compounds of the following type
(277) ##STR00179##
(278) wherein R.sup.1 is chloro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
(279) Table 60 covers compounds of the following type
(280) ##STR00180##
(281) wherein R.sup.1 is fluoro, R.sup.4 is hydrogen, R.sup.10 is methyl and all of R.sup.2, R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are hydrogen. R.sup.3 is as defined in Table 53.
BIOLOGICAL EXAMPLES
Biological Example 1 (Biological Examples 1A and 1B)
Test 1Glasshouse Assay for Herbicidal Activity
(282) Seeds of a variety of test species are sown in standard soil in pots. After cultivation for one day (pre-emergence) or after 8 days cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16 C., day/night; 14 hours light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical (i.e. unformulated) active ingredient in acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS Registry Number 9005-64-5). The test plants are then grown on under controlled conditions in a glasshouse (at 24/16 C., day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days for pre- or post-emergence, the test is evaluated visually, and an assessed percentage phytotoxicity score is given for each herbicidal application on each plant species (where 100%=total damage to plant; 0%=no damage to plant).
Biological Example 1APre-Emergence Herbicidal Activity
(283) Test plants include the following: Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE): these are dicotyledonous (broadleaved) weeds. Setaria faberi (SETFA), Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG): these are grassy monocotyledonous weeds. Also: Zea mays (ZEAMX, corn/maize), which can be a grassy weed (volunteer corn) in some circumstances.
Biological Example 1ATable of Pre-Emergence Herbicidal Activity (Percentage Phytotoxicity)
(284) TABLE-US-00013 Application Compound Rate Number (g/ha) ABUTH AMARE SETFA ALOMY ECHCG ZEAMX A1 250 - 80 90 100 100 - A2 250 50 90 100 90 100 100 A3 250 20 60 100 100 100 100 A4 250 0 80 100 90 100 100 A5 250 70 100 100 100 100 100 A6 250 40 90 100 90 100 90 A7 250 0 70 100 90 100 100 A8 250 0 90 100 90 100 90 A9 250 40 70 100 70 100 80 A10 250 60 100 100 100 100 100 A11 250 40 80 100 100 100 100 A12 250 80 100 100 90 100 100 A13 250 80 100 100 90 100 100 A14 250 20 90 100 100 100 100 A16 250 40 40 90 90 90 80 A17 250 10 10 70 70 70 60 A18 250 20 40 70 60 60 30 A19 250 40 40 60 60 50 0 A20 250 70 70 100 90 100 100 A21 250 10 0 90 80 90 100 A22 250 0 30 90 80 100 100 A23 250 - - - 100 100 - A24 250 - - - 100 100 - A25 250 - - - 100 100 - A26 250 - - - 30 80 - A27 250 - - - 100 100 - A28 250 - - - 90 100 - A29 250 - - - 70 90 - A42 250 - - - 100 80 - A45 250 - 90 60 100 100 - Note: a hyphen (-) in the table above indicates that no measurement was made.
Biological Example 1BPost-Emergence Herbicidal Activity
Biological Example 1BTable 1 of Post-Emergence Herbicidal Activity (Percentage Phytotoxicity)
(285) Test plants include the following: Abutilon theophrasti (ABUTH) and Amaranthus retroflexus (AMARE); these are all dicotyledonous (broadleaved) weeds. Setaria faberi (SETFA), Alopecurus myosuroides (ALOMY), and Echinochloa crus-galli (ECHCG); these are all grassy monocotyledonous weeds. Also: Zea mays (ZEAMX, corn/maize), which can be a grassy weed (volunteer corn) in some circumstances.
(286) TABLE-US-00014 Application Compound Rate Number (g/ha) ABUTH AMARE SETFA ALOMY ECHCG ZEAMX A1 250 - 70 100 100 100 - A1 62.5 - 30 90 90 100 - A2 250 80 70 100 90 100 100 A2 62.5 70 70 100 90 100 100 A3 250 90 90 100 100 100 100 A3 62.5 80 60 100 100 100 100 A4 250 80 80 100 100 100 100 A4 30 40 60 100 70 90 100 A5 250 90 90 100 100 100 100 A5 31.25 30 30 100 80 100 100 A6 250 70 70 100 100 100 100 A6 30 40 60 100 80 100 100 A7 250 80 80 100 100 100 100 A7 30 30 20 100 70 100 100 A8 250 80 90 100 100 100 100 A8 30 70 80 100 100 100 100 A9 250 80 80 100 100 100 100 A10 250 80 80 100 100 100 100 A10 30 80 80 100 90 100 100 A11 250 80 80 100 100 100 100 A11 30 30 50 100 70 100 100 A12 250 80 80 100 100 100 100 A12 30 50 30 100 80 100 100 A13 250 80 90 100 100 100 100 A13 30 70 60 100 90 100 100 A14 250 0 60 100 90 100 100 A14 62.5 0 50 90 70 100 100 A15 250 60 40 70 10 70 80 A16 250 40 60 90 90 100 60 A16 30 40 0 80 70 40 80 A17 250 10 50 80 70 80 60 A18 250 60 60 80 70 80 80 A18 30 0 0 60 10 60 60 A19 250 30 20 90 60 90 30 A19 30 0 0 70 10 70 40 A20 250 60 70 100 100 100 100 A20 30 0 0 80 50 80 90 A21 250 40 30 100 70 100 100 A21 30 0 10 80 40 90 100 A22 250 40 80 100 100 100 100 A22 30 0 10 90 70 90 100 A43 250 - 0 70 20 20 - A44 250 10 0 0 0 0 20 A44 8 0 0 0 0 0 30 A45 250 - 80 100 100 100 - A45 62.5 - 20 90 90 100 - Note: a hyphen (-) in the table above indicates that no measurement was made.
Biological Example 1BTable 2 of Post-Emergence Herbicidal Activity (Percentage Phytotoxicity)
(287) Test plants include the following:
(288) Lolium perenne (LOLPE), Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), and Avena fatua (AVEFA); these are all grassy monocotyledonous weeds. Cool climate crop plant: Triticum aestivum (TRZAW, winter wheat).
(289) TABLE-US-00015 Application Compound Rate Number (g/ha) LOLPE TRZAW ALOMY ECHCG AVEFA A2 250 100 90 100 100 100 A2 62.5 70 70 70 90 80 A3 250 100 90 100 100 100 A3 62.5 100 90 100 100 90 A5 250 100 90 100 100 100 A5 62.5 90 80 90 100 100 A6 250 80 80 100 100 90 A8 250 100 80 100 100 100 A8 62.5 70 80 80 100 90 A10 250 100 90 100 100 100 A10 62.5 100 90 100 100 100 A12 250 100 80 100 100 100 A12 62.5 70 70 60 100 60 A13 250 100 80 100 100 100 A13 62.5 90 80 100 100 100 A14 250 80 70 90 100 100 A23 250 100 70 100 100 90 A23 62.5 90 50 90 100 90 A24 250 80 0 80 80 50 A24 62.5 70 0 60 70 60 A25 250 100 60 100 100 100 A25 62.5 100 30 90 100 100 A26 250 100 10 60 100 70 A27 250 100 90 100 100 100 A27 62.5 80 80 90 90 90 A28 250 90 80 100 100 90 A28 62.5 80 30 70 90 80 A29 250 80 80 80 100 60 A29 62.5 60 60 60 90 0 A42 250 100 20 90 100 80
Biological Example 2
Test 2Glasshouse Assay for Herbicidal Activity
(290) Seeds of a variety of monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. The plants are cultivated for one day (for pre-emergence) or for about 12 days (for post-emergence) under controlled conditions in a glasshouse (warm climate species at 24/18 C., cool climate species at 20/16 C., both at day/night; 16 hours light; 65% humidity).
(291) An instant formulation, known as the IF50, containing 50 g/liter (i.e. 5% w/v) of the technical (i.e. unformulated) active ingredient is prepared by dissolving the active ingredient in a mixture of organic solvents and emulsifier, details of which are provided in the Table below. This IF50 is then mixed with a small, variable amount of acetone to aid dissolution, before addition of a 0.2% v/v aqueous solution of the adjuvant X-77 (which is a mixture of alkyl aryl polyoxyethylene glycols and free fatty acids in isopropanol, CAS Registry number 11097-66-8), as the aqueous diluent, to form an aqueous spray solution which contains a predetermined concentration of the active ingredient (which varies depending on the application rate of the active ingredient to the plants) and 0.2% v/v of the adjuvant X-77. This aqueous spray solution is then sprayed onto the plants, after one day's cultivation (for pre-emergence), or after about 12 days' cultivation (range=10-13 days) (for post-emergence).
(292) TABLE-US-00016 TABLE Composition of the mixture of organic solvents and emulsifier to be used as a base for the instant formulation (IF50). CAS Chemical Registry Amount/ Component Supplier description number % w/w Emulsogen Clariant castor oil ethoxylate 61791-12-6 11.12 EL360 (as emulsifier) N-methyl- widely 1-methyl-2- 872-50-4 44.44 pyrrolidone available pyrrolidone Dowanol Dow dipropylene glycol 34590-94-8 44.44 DPM monomethyl ether glycol ether
(293) The test plants are then grown on, in a glasshouse (greenhouse) under controlled conditions (warm climate species at 24/18 C., cool climate species at 20/16 C., both at day/night; 16 hours light; 65% humidity) and are watered twice daily. 15 days after application of the test herbicide (15DAA) (for post-emergence), and 20 days after application of the test herbicide (20DAA) (for pre-emergence), the test plants are evaluated visually, and an assessed percentage phytotoxicity score is given for each herbicidal application on each plant species (with 100%=total damage to plant; 0%=no damage to plant).
(294) Some of the typical test plants are as follows:
(295) Cool climate crop plants: Triticum aestivum (TRZAW, winter wheat), Brassica napus (BRSNN, rape, also called oilseed rape or rapeseed), Beta vulgaris (BEAVA, sugarbeet). Warm climate crop plants: Glycine max (GLXMA, soybean).
(296) Cool climate (cool season) grassy monocotyledonous weeds: Alopecurus myosuroides (ALOMY), Avena fatua (AVEFA), Lolium perenne (LOLPE).
(297) Warm climate (warm season) grassy monocotyledonous weeds: Setaria faberi (SETFA), Panicum miliaceum (PANMI), Sorghum vulgare Pers. (SORVU) (or Sorghum bicolor (L) Moench ssp. Bicolor), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), and Brachiaria plantaginea (BRAPL).
Biological Example 2Table of Pre-Emergence Herbicidal Activity (Percentage Phytotoxicity)
(298) TABLE-US-00017 Application Compound Rate Number (g/ha) LOLPE SETFA PANMI SORVU DIGSA ECHCG BRAPL A1 125 80 100 100 90 100 90 90 A2 250 80 90 100 80 70 80 80 A3 250 80 80 80 80 90 80 90 A6 250 30 0 0 40 20 50 - A7 250 60 90 100 90 100 90 90 A8 250 80 70 90 80 80 60 - A10 250 70 100 100 100 100 100 - A11 250 60 90 60 80 90 70 100 A12 250 100 100 100 90 100 80 100 A13 250 100 100 100 100 100 100 100 A14 250 70 100 100 90 100 80 100 A15 250 0 20 20 30 50 10 - A22 250 20 90 80 70 90 70 90 A23 250 100 90 100 70 90 100 - A25 250 90 80 90 90 100 100 100 A42 500 100 80 100 80 70 100 100 A45 125 90 90 100 80 90 80 90 Note: a hyphen (-) in the table above indicates that no measurement was made.
Biological Example 2Table of Post-Emergence Herbicidal Activity (Percentage Phytotoxicity)
(299) TABLE-US-00018 Application Compound Rate Number (g/ha) TRZAW GLXMA BRSNN BEAVA ALOMY AVEFA A1 125 80 0 70 70 80 100 A1 30 80 0 70 70 60 70 A2 250 90 20 80 50 100 90 A2 30 70 10 50 40 20 60 A3 250 90 70 70 70 100 100 A3 30 80 20 40 40 80 40 A6 250 90 10 40 40 100 80 A6 125 80 10 20 20 80 70 A7 250 90 20 80 70 100 100 A7 30 50 0 60 20 10 20 A8 250 90 40 80 60 80 90 A8 30 30 20 70 10 50 50 A10 250 80 70 80 80 100 100 A10 30 70 40 80 60 50 60 A11 250 90 20 70 70 70 70 A11 30 60 0 30 20 30 20 A12 125 80 0 60 40 80 80 A12 30 40 0 50 40 60 10 A13 125 80 30 80 70 100 80 A13 30 40 20 70 60 30 30 A14 125 40 0 0 10 60 40 A15 250 10 10 60 40 40 10 A18 250 30 40 20 50 30 30 A19 250 30 20 10 0 40 10 A22 125 70 40 70 0 70 70 A22 30 20 0 50 0 50 0 A23 125 20 0 70 30 90 80 A25 125 60 0 20 0 80 100 A25 30 10 0 0 0 50 80 A42 500 10 10 80 30 70 50 A42 125 0 10 20 0 50 0 A45 125 80 10 80 70 90 90 A45 30 80 0 50 70 70 70 Compound Number LOLPE SETFA PANMI SORVU DIGSA ECHCG BRAPL A1 80 100 100 100 100 100 100 A1 70 90 80 90 100 100 100 A2 90 100 100 100 100 100 100 A2 30 100 100 100 100 100 100 A3 90 100 100 100 100 100 100 A3 30 100 100 100 100 100 80 A6 70 100 100 100 100 100 - A6 30 100 100 100 100 100 - A7 80 100 100 100 100 100 100 A7 30 90 100 100 100 100 100 A8 60 100 100 100 100 100 - A8 40 90 100 100 90 70 - A10 90 100 100 100 100 100 - A10 30 100 100 100 100 100 - A11 40 100 100 100 100 100 100 A11 30 80 100 100 100 100 100 A12 90 100 100 100 100 100 100 A12 30 20 70 90 70 70 70 A13 80 100 100 100 100 100 100 A13 10 100 100 100 100 100 90 A14 20 90 60 100 100 100 30 A15 20 30 70 40 30 70 - A18 10 70 60 70 50 90 - A19 10 60 70 70 70 70 - A22 50 100 100 100 100 100 100 A22 10 80 60 70 70 70 90 A23 90 80 100 90 100 100 - A25 100 100 100 100 100 100 100 A25 90 90 100 100 100 100 100 A42 100 100 100 100 100 100 100 A42 80 90 100 80 90 100 100 A45 100 100 100 100 100 100 100 A45 80 90 100 70 100 100 90 Note: a hyphen (-) in the table above indicates that no measurement was made.
Biological Example 3Assay for Biological Example 3Glasshouse Assay for Herbicidal Activity, Using Various Adjuvant Systems
(300) Materials and Methods
(301) Herbicide Application:
(302) Post-emergence foliar spray application, 200 L/ha, usually one or two replicates for the weeds (depending on application rate), and two replicates for soybean.
(303) Climate:
(304) Standard warm conditions (tropical), in glasshouse. Specifically, the glasshouse bay conditions are 24 C./18 C. day/night; 16/8 hours light/dark; 65% humidity.
(305) Plants:
(306) The herbicidal application takes place at the following growth stages for plants which include inter alia one or more of the following plants (usually the herbicidal application takes place on at least the following plants: DIGSA, ELEIN, SETFA, ZEAMX, GLXMA Nikko, and GLXMA TMG133, and often also either BRADC or BRAPP):
(307) Brachiaria decumbens (BRADC)growth stage (GS) 12 or 13 (or GS 12)or, if BRADC is not used, then sometimes Brachiaria platyphylla (BRAPP)growth stage 12 or 13
(308) Digitaria sanguinalis (DIGSA)growth stage 12 or 13
(309) Eleusine indica (ELEIN)growth stage 12 or 13
(310) Setaria faberi (SETFA)growth stage 12 or 13
(311) Echinochloa crus-galli (ECHCG)growth stage 12 or 13
(312) Sorghum halepense (annual) (SORHA)growth stage 12 or 13
(313) Panicum dichotomiflorum (PANDI)growth stage 12 or 13
(314) Zea mays (ZEAMX, maize/corn, e.g. can occur as volunteer corn) cultivar Garlandgrowth stage 12 or 13
(315) Glycine max (GLXMA, soybean) cultivar Nikkogrowth stage: 1.sup.st trifoliate
(316) Glycine max (GLXMA, soybean) cultivar TMG133which is Roundup Ready glyphosate-tolerant soybean cultivar TMG133 (typically available from Monsanto in Brazil)growth stage: 1.sup.st trifoliate.
(317) Herbicidal Compositions Tested:
(318) Each test compound is applied with one of the following adjuvant systems (all percentages are final concentrations in the aqueous spray mixture):
(319) Adjuvant system 1: 0.5% v/v Adigor*, 1.0% v/v AMS (ammonium sulphate) and 12.5% v/v IPA (isopropyl alcohol).
(320) Adjuvant system 1A: 0.5% v/v Adigor* and 12.5% v/v IPA (isopropyl alcohol).
(321) Adjuvant system 2: 0.5% v/v Hexamoll DINCH**, 1.0% v/v AMS (ammonium sulphate) and 12.5% v/v IPA (isopropyl alcohol).
(322) Adjuvant system 3: 0.5% v/v tris-(2-ethylhexyl)phosphate (TEHP), 1.0% v/v AMS (ammonium sulphate) and 12.5% v/v IPA (isopropyl alcohol).
(323) *Adigor (currently available in many countries from Syngenta) is an emulsifiable concentrate which consists of:
(324) (i) ethoxylated alcohols, which typically includes ethoxylated higher alcohols (e.g. ethoxylates of alcohols wherein the alcohols are within the range of C.sub.12-C.sub.22); and
(325) (ii) a mixture of heavy aromatic hydrocarbons, which typically includes (e.g. includes 50% or more by weight of the heavy aromatic hydrocarbons of) a mixture of naphthalenes each of which is substituted by one or more alkyls wherein the alkyl(s) in total have 1-4 carbon atoms per naphthalene molecule (e.g. Solvesso 200 ND); and
(326) (iii) about 47% w/w and/or about 45% w/v (with respect to the emulsifiable concentrate) of methylated rapeseed oil (rapeseed oil methyl ester) (e.g. Agnique ME 18 RD-F), as an adjuvant.
(327) ** Hexamoll DINCH is 1,2-cyclohexane dicarboxylic acid di-isononyl ester
(328) ##STR00181##
CAS Registry no. 166412-78-8), and is usually available from BASF. Isononyl in this context is thought to mean a mixture of two or more branched isomers of C.sub.9H.sub.19.
Method:
(329) Seeds of the weed (including volunteer) plants, typically including inter alia Digitaria sanguinalis (DIGSA), Eleusine indica (ELEIN), Setaria faberi (SETFA), Zea mays (ZEAMX, corn), and sometimes also [either Brachiaria decumbens (BRADC) or Brachiaria platyphylla (BRAPP)], are sown in seed trays (troughs) containing clay loam soil (pH 7.0, 2.2% organic matter, Trough Mix A); and soybean seed is sown in pots containing the same soil with 3 soybean seedlings per pot. The plants are sprayed with the test herbicide when they reach the growth stages mentioned above.
(330) The test herbicidal solutions are prepared by mixing the appropriate aliquots of the test substance(s) and one of the adjuvant systems indicated above *** in deionised water to give the desired treatment concentration.
(331) The herbicidal application is made as a foliar spray, using a tracksprayer. Following the herbicidal application, the plants are watered twice per day for the duration of the test.
(332) A visual assessment of the % herbicidal damage is made 7 and 14 Days After herbicide Application (DAA) (or, in a minority of cases, 7 and 15 DAA), and the results are recorded as % visual herbicidal damage where 0%=no damage to plants and 100%=plant totally killed.
(333) ***Adjuvant system=either Adigor or Hexamoll DINCH or tris-(2-ethylhexyl)phosphate each at 0.5% v/v, and 12.5% v/v IPA (isopropyl alcohol), and 1.0% v/v AMS (ammonium sulphate); or 0.5% v/v Adigor and 12.5% v/v IPA (isopropyl alcohol); all percentages are final concentrations in the aqueous spray mixture.
Biological Example 3Post-Emergence ActivityResults at 14 or 15 Days After Herbicide Application
(334) Compounds A2, A7, A11, A12, A14, A20 and A21, which are compounds of formula (I) according to the present invention, were tested in a test method substantially as described above.
(335) Compounds A2 and A7 were tested using the 0.5% v/v Hexamoll DINCH+1.0% v/v AMS+12.5% v/v IPA adjuvant system. Compounds A11, A12, A14, A20 and A21 were tested using the 0.5% v/v tris-(2-ethylhexyl)phosphate (TEHP)+1.0% v/v AMS+12.5% v/v IPA adjuvant system.
(336) The percentages of herbicidal damage/plant control, at 14 Days After herbicide Application (DAA) (or, in some cases, at 15 DAA), for the Compounds tested and for some of the plants tested, were in the following percentage ranges. For the tested compounds, the phytotoxicity results shown herein are generally the average of 2 or 3 repetitions (for the grassy weeds including corn) or the average of 2 repetitions (for soybean for most of the tested compounds). However, for Compound A2 on soybean there was 1 repetion only.
(337) Control of Brachiaria decumbens (BRADC), a Warm-Climate (Warm-Season) Grassy Weed
(338) At 14 DAA, Compound A2 showed a percentage control of (phytotoxicity on) Brachiaria decumbens (BRADC) of 50% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(339) At 14 DAA, Compound A7 showed a percentage control of Brachiaria decumbens of 95% (as an average of 3 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(340) At 14 DAA, Compound A11 showed a percentage control of Brachiaria decumbens of 99% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(341) At 14 or 15 DAA, Compound A12 showed a percentage control of Brachiaria decumbens (BRADC) of 99%, when applied post-emergence at an application rate of 8 g/ha.
(342) Control of Digitaria sanguinalis (DIGSA), a Warm-Climate (Warm-Season) Grassy Weed
(343) At 14 DAA, Compound A2 showed a percentage control of (phytotoxicity on) Digitaria sanguinalis (DIGSA) of 90% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(344) At 14 DAA, Compound A7 showed a percentage control of Digitaria sanguinalis of 95% (as an average of 3 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(345) At 14 DAA, Compound A11 showed a percentage control of Digitaria sanguinalis of 99% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(346) At 14 or 15 DAA, Compound A12 showed a percentage control of Digitaria sanguinalis of 98.5%, when applied post-emergence at an application rate of 8 g/ha.
(347) At 15 DAA, Compound A14 showed a percentage control of Digitaria sanguinalis of 85% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(348) At 14 or 15 DAA, Compound A20 showed a percentage control of Digitaria sanguinalis of 75%, when applied post-emergence at an application rate of 8 g/ha.
(349) At 14 or 15 DAA, Compound A21 showed a percentage control of Digitaria sanguinalis of 45%, when applied post-emergence at an application rate of 8 g/ha.
(350) Control of Eleusine indica (ELEIN), a Warm-Climate (Warm-Season) Grassy Weed
(351) At 14 DAA, Compound A2 showed a percentage control of (phytotoxicity on) Eleusine indica (ELEIN) of 85% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(352) At 14 DAA, Compound A7 showed a percentage control of Eleusine indica of 91.7% (as an average of 3 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(353) At 14 DAA, Compound A11 showed a percentage control of Eleusine indica of 95% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(354) At 14 or 15 DAA, Compound A12 showed a percentage control of Eleusine indica of 90%, when applied post-emergence at an application rate of 8 g/ha.
(355) At 15 DAA, Compound A14 showed a percentage control of Eleusine indica of 20% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(356) At 14 or 15 DAA, Compound A20 showed a percentage control of Eleusine indica of 15%, when applied post-emergence at an application rate of 8 g/ha.
(357) At 14 or 15 DAA, Compound A21 showed a percentage control of Eleusine indica of 25%, when applied post-emergence at an application rate of 8 g/ha.
(358) Control of Setaria faberi (SETFA), a Warm-Climate (Warm-Season) Grassy Weed
(359) At 14 DAA, Compound A2 showed a percentage control of (phytotoxicity on) Setaria faberi (SETFA) of 90% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(360) At 14 DAA, Compound A7 showed a percentage control of Setaria faberi of 91.7% (as an average of 3 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(361) At 14 DAA, Compound A11 showed a percentage control of Setaria faberi of 98% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(362) At 14 or 15 DAA, Compound A12 showed a percentage control of Setaria faberi of 95%, when applied post-emergence at an application rate of 8 g/ha.
(363) At 15 DAA, Compound A14 showed a percentage control of Setaria faberi of 95% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(364) At 14 or 15 DAA, Compound A20 showed a percentage control of Setaria faberi of 90%, when applied post-emergence at an application rate of 8 g/ha.
(365) At 14 or 15 DAA, Compound A21 showed a percentage control of Setaria faberi of 85%, when applied post-emergence at an application rate of 8 g/ha.
(366) Control of Zea mays (ZEAMX, Corn), a Warm-Climate (Warm-Season) Grassy Plant
(367) Zea mays (ZEAMX, maize, corn) is often present as a volunteer weed (volunteer corn) in fields where it was planted as a crop in preceding growing season(s) and where the present field crop is not corn.
(368) At 14 DAA, Compound A2 showed a percentage control of (phytotoxicity on) Zea mays (ZEAMX, maize, corn) of 10% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(369) At 14 DAA, Compound A7 showed a percentage control of Zea mays of 100% (as an average of 3 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(370) At 14 DAA, Compound A11 showed a percentage control of Zea mays of 100% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(371) At 14 or 15 DAA, Compound A12 showed a percentage control of Zea mays of 100%, when applied post-emergence at an application rate of 8 g/ha.
(372) At 15 DAA, Compound A14 showed a percentage control of Zea mays of 90% (as an average of 2 repetitions), when applied post-emergence at an application rate of 8 g/ha.
(373) At 14 or 15 DAA, Compound A20 showed a percentage control of Zea mays of 90%, when applied post-emergence at an application rate of 8 g/ha.
(374) At 14 or 15 DAA, Compound A21 showed a percentage control of Zea mays of 95%, when applied post-emergence at an application rate of 8 g/ha.
(375) Phytotoxicity on Glycine max (GLXMA, Soybean) Cultivar Nikko
(376) At 14 DAA, Compound A2 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 10% (1 repetition only), when applied post-emergence at an application rate of 120 g/ha.
(377) At 14 DAA, Compound A7 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 2.5% (as an average of 2 repetitions), when applied post-emergence at an application rate of 120 g/ha.
(378) At 14 DAA, Compound A11 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 15% (as an average of 2 repetitions), when applied post-emergence at an application rate of 120 g/ha.
(379) At 14 or 15 DAA, Compound A12 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 15%, when applied post-emergence at an application rate of 240 g/ha.
(380) At 15 DAA, Compound A14 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 5% (as an average of 2 repetitions), when applied post-emergence at an application rate of 120 g/ha.
(381) At 14 or 15 DAA, Compound A20 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 2%, when applied post-emergence at an application rate of 120 g/ha.
(382) At 14 or 15 DAA, Compound A21 showed a percentage phytotoxicity on Glycine max cultivar Nikko of 5%, when applied post-emergence at an application rate of 120 g/ha.
(383) Phytotoxicity on Glycine max (GLXMA, Soybean) Cultivar TMG133
(384) Glycine max (GLXMA, soybean) cultivar TMG133 is Roundup Ready glyphosate-tolerant soybean cultivar TMG133, and is typically available from Monsanto in Brazil.
(385) At 14 DAA, Compound A2 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 20% (1 repetition only), when applied post-emergence at an application rate of 120 g/ha.
(386) At 14 DAA, Compound A7 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 0% (as an average of 2 repetitions), when applied post-emergence at an application rate of 120 g/ha.
(387) At 14 DAA, Compound A11 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 12.5% (as an average of 2 repetitions), when applied post-emergence at an application rate of 120 g/ha.
(388) At 14 or 15 DAA, Compound A12 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 15%, when applied post-emergence at an application rate of 240 g/ha.
(389) At 15 DAA, Compound A14 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 5% (as an average of 2 repetitions), when applied post-emergence at an application rate of 120 g/ha.
(390) At 14 or 15 DAA, Compound A20 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 10%, when applied post-emergence at an application rate of 120 g/ha.
(391) At 14 or 15 DAA, Compound A21 showed a percentage phytotoxicity on Glycine max cultivar TMG133 of 5%, when applied post-emergence at an application rate of 120 g/ha.