Herbicidal compounds

Patent metadata

Field	Value
Publication number	US-10206394-B2
Application number	US-201515520233-A
Country	US
Kind code	B2
Filing date	Oct 13, 2015
Priority date	Oct 20, 2014
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

The present invention relates to a compound of formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and G are as defined herein; and wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are 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 selected from the group consisting of methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, difluoromethoxy and 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 2A is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, C 1 -C 2 fluoroalkyl, vinyl, prop-1-enyl, prop-1-ynyl, —C≡C—R 2AA , halogen and (C 1 -C 2 fluoroalkyl)-methoxy-; wherein R 2AA is selected from the group consisting of hydrogen, fluorine, chlorine, trifluoromethyl, ethyl and cyclopropyl;
or R 2A is phenyl optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 3 alkoxy, C 1 -C 2 fluoroalkoxy, —S(O) p methyl, cyano or nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, —S(O) p methyl or nitro;
or R 2A is a monocyclic heteroaryl optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 3 alkoxy, C 1 -C 2 fluoroalkoxy, —S(O) p methyl, cyano and nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, —S(O) p methyl or nitro;
R 3A is selected from the group consisting of hydrogen, methyl, fluorine and chlorine;
and wherein
R 2B is hydrogen, methyl or fluorine; and
either R 3B is phenyl optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, —S(O) p methyl, cyano and nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, —S(O) p methyl or nitro; or
R 3B is a monocyclic heteroaryl optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, methoxymethyl, vinyl, ethynyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, —S(O) p methyl, cyano and nitro, provided that either one or none (i.e. no more than one) of these optional substituents are methoxymethyl, vinyl, ethynyl, —S(O) p methyl or nitro;
R 4 is selected from the group consisting of 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-;
R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 2 haloalkyl and C 1 -C 2 alkoxyC 1 -C 2 alkyl;
R 8 and R 9 are independently selected from the group consisting of hydrogen, fluorine and C 1 -C 3 alkyl;
R 10 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkylcyano, C 1 -C 6 alkoxyC 1 -C 6 -alkyl-, C 1 -C 6 alkoxy-C 2 -C 6 -alkenyl-, C 1 -C 6 alkoxy-C 2 -C 6 -alkynyl-, C 1 -C 6 alkenyloxyC 1 -C 6 -alkyl-, C 1 -C 6 alkoxy-C 2 -C 3 -alkoxy-C 2 -C 3 -alkyl-, C 1 -C 6 alkylcarbonyl- and C 1 -C 6 alkylcarbonylC 1 -C 6 -alkyl-;
R 11 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkylcyano, C 1 -C 6 alkoxyC 1 -C 6 -alkyl-, C 1 -C 6 alkoxy-C 2 -C 6 -alkenyl-, C 1 -C 6 alkoxy-C 2 -C 6 -alkynyl-, C 1 -C 6 alkenyloxyC 1 -C 6 -alkyl-, C 1 -C 6 alkoxy-C 2 -C 3 -alkoxy-C 2 -C 3 -alkyl-, C 1 -C 6 alkylcarbonyl-, C 1 -C 6 alkylcarbonylC 1 -C 6 -alkyl-; or
R 11 is —(CR′R″) n —X 1 —R 13 wherein X 1 is a bond, —(CH═CH)— or —(C═O)— and wherein R′ and R″ are independently selected from hydrogen and methyl or together from a C 2 -C 3 alkylene chain); or
R 10 and R 11 together form a four to six membered heterocycle, the heterocycle comprising one or more heteroatoms selected from the group consisting of oxygen, nitrogen and sulphur; the heterocycle being optionally substituted by one or more independent R 12 ;
R 12 is selected from the group consisting of halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy-, nitro, —(CO)OR 14 , cyano, phenyl, pyridyl;
R 13 is a three- to ten-membered mono- or bicyclic ring system, which may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each independently selected from the group consisting of nitrogen, oxygen and sulphur the ring system being optionally substituted by one or more R 12 substituents;
R 14 is H or C 1 -C 6 alkyl;
n=0, 1, 2, 3 or 4;
p=0, 1 or 2; and
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 2 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 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)

Assignees

• Syngenta Participations Ag

Inventors

• Hennessy Alan Joseph
• Hachisu Shuji
• Wailes Jeffrey Steven
• Willetts Nigel James
• Cloudsdale Ian Stuart
• Black Janice
• Briggs Emma
• Dale Suzanna Jane

Classifications

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D305/08

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms · CPC title

• C07D277/64

  with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 · CPC title

• A01N43/16

  with oxygen as the ring hetero atom · CPC title

• C07D333/28

  Halogen atoms · CPC title