Herbicidally active 2-(substituted-phenyl)-cyclopentane-1,3-dione compounds and derivatives thereof

Patent metadata

Field	Value
Publication number	US-10375956-B2
Application number	US-201414896472-A
Country	US
Kind code	B2
Filing date	Jun 3, 2014
Priority date	Jun 5, 2013
Publication date	Aug 13, 2019
Grant date	Aug 13, 2019

Abstract

The present invention relates to a compound of formula (I): wherein: R 8 and R 9 , independently of each other, are hydrogen, fluorine or C 1 -C 3 alkyl; R 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.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein:
R 1 is methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, difluoromethoxy or trifluoromethoxy; and
either (a): R 2 is R 2A and R 3 is R 3A ;
or (b): R 2 is R 2B and R 3 is R 3B ;
wherein:
R 3A is hydrogen, methyl, fluorine or chlorine; and
R 2A is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, C 1 -C 2 fluoroalkyl, vinyl, prop-1-enyl, —C≡C—R 2AA , halogen, or (C 1 -C 2 fluoroalkyl)-methoxy-; wherein R 2AA is hydrogen, fluorine, trifluoromethyl, ethyl or cyclopropyl;
or R 2A is phenyl optionally substituted by 1, 2 or 3 substituents independently being halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 3 alkoxy, C 1 -C 2 fluoroalkoxy, 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 2A is monocyclic heteroaryl optionally substituted by 1, 2 or 3 substituents independently being halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 3 alkoxy, C 1 -C 2 fluoroalkoxy, 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 2B is hydrogen, methyl or fluorine; and
either R 3B is phenyl optionally substituted by 1, 2 or 3 substituents independently being halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, 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 3B is monocyclic heteroaryl optionally substituted by 1, 2 or 3 substituents independently being halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, 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 4 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, C 1 -C 3 alkoxy, C 1 -C 2 fluoroalkoxy, C 1 -C 2 alkoxy-C 1 -C 3 alkoxy-, or C 1 fluoroalkoxy-C 1 -C 3 alkoxy-; and
R 5 , R 6 and R 7 , independently of each other, are hydrogen, C 1 -C 5 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 2 fluoroalkyl or C 1 -C 2 alkoxyC 1 -C 2 alkyl;
provided that: either (i) at least two of R 5 , R 6 and R 7 are hydrogen, or (ii) two of R 5 , R 6 and R 7 are methyl and the remaining one of R 5 , R 6 and R 7 is hydrogen; and
R 8 and R 9 , independently of each other, are hydrogen, fluorine or C 1 -C 3 alkyl; and
R 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 a )—R a , C(X b )—X c —R b , C(X d )—N(R c )—R d , —SO 2 —R e , —P(X e )(R f )—R g , CH 2 —X f —R h ; or
phenyl-CH 2 — or phenyl-CH(C 1 -C 2 alkyl)- (in each of which the phenyl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 2 alkyl, C 1 fluoroalkyl, C 1 -C 2 alkoxy, C 1 fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or heteroaryl-CH 2 — or heteroaryl-CH(C 1 -C 2 alkyl)- (in each of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 2 alkyl, C 1 fluoroalkyl, C 1 -C 2 alkoxy, C 1 fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or phenyl-C(O)—CH 2 — (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 2 alkyl, C 1 fluoroalkyl, C 1 -C 2 alkoxy, C 1 fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro); or C 1 -C 6 alkoxy-C(O)—CH 2 —, C 1 -C 6 alkyl-C(O)—CH 2 —, C 1 -C 6 alkoxy-C(O)—CH═CH—, C 2 -C 7 alken-1-yl-CH 2 —, C 2 -C 7 alken-1-yl-CH(C 1 -C 2 alkyl)-, C 2 -C 4 fluoroalken-1-yl-CH 2 —, C 2 -C 7 alkyn-1-yl-CH 2 —, or C 2 -C 7 alkyn-1-yl-CH(C 1 -C 2 alkyl)-;
wherein X a , X b , X c , X d , X e and X f are independently of each other oxygen or sulfur; and wherein
R a is H, C 1 -C 21 alkyl, C 2 -C 21 alkenyl, C 2 -C 18 alkynyl, C 1 -C 10 fluoroalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy (C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 1 -C 5 )alkylamino(C 1 -C 5 )alkyl, C 3 -C 6 trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or nitro), C 2 -C 5 fluoroalkenyl, C 3 -C 8 cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkoxy, halogen, cyano or nitro;
R b is C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 18 alkynyl, C 2 -C 10 fluoroalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 2 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 1 -C 5 )alkylamino(C 1 -C 5 )alkyl, C 3 -C 6 trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or nitro), heteroarylC 1 -C 5 alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C 1 -C 3 alk

Assignees

• Syngenta Ltd

Inventors

• Aspinall Ian Henry
• Jeanmart Stephane Andre Marie
• Scutt James Nicholas
• Taylor John Benjamin

Classifications

• C07D239/30

  Halogen atoms or nitro radicals · CPC title

• C07D213/61

  Halogen atoms or nitro radicals · CPC title

• C07C49/747

  containing six-membered aromatic rings · CPC title

• C07D213/50

  Ketonic radicals · CPC title

• C07C69/157

  containing six-membered aromatic rings · CPC title