Herbicidally active cyclic dione compounds, or derivatives therefor, substituted by a phenyl which has an alkynyl-containing substituent

Patent metadata

Field	Value
Publication number	US-9615577-B2
Application number	US-201314653674-A
Country	US
Kind code	B2
Filing date	Dec 19, 2013
Priority date	Dec 21, 2012
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

The present invention relates to a compound of formula (I), wherein: X is methyl or chlorine; R 1 is methyl or chlorine; R 2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, 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 Y is O, S, S(O), S(O) 2 , N(C 1 -C 2 alkyl), N(C 1 -C 2 alkoxy), C(O), CR 8 R 9 or —CR 10 R 11 CR 12 R 13 —; and G, R 3 , R 4 , R 5 and R 6 are as defined herein; 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:
X is methyl or chlorine;
R 1 is methyl or chlorine;
R 2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, 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 3 , R 4 , R 5 and R 6 , independently of each other, are hydrogen, C 1 -C 5 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 2 fluoroalkyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkylthioC 1 -C 3 alkyl, C 1 -C 3 alkylsulfinylC 1 -C 3 alkyl, C 1 -C 3 alkylsulfonylC 1 -C 3 alkyl; C 3 -C 4 cycloalkyl; or an unsubstituted 4, 5 or 6 membered monocyclic heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and nitrogen, and attached at a ring carbon atom within the heterocyclyl;
provided that no more than one of R 3 , R 4 , R 5 and R 6 is alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
or R 3 and R 4 taken together are —(CH 2 ) n1 — or —(CH 2 ) n2 —X 1 —(CH 2 ) n3 — and R 5 and R 6 are as defined herein, or R 5 and R 6 taken together are —(CH 2 ) n1 — or —(CH 2 ) n2 —X 1 —(CH 2 ) n3 — and R 3 and R 4 are as defined herein;
wherein X 1 is O, S, S(O), S(O) 2 , NH, N(C 1 -C 2 alkyl), N(C 1 -C 2 alkoxy), C(H)(C 1 -C 2 alkyl), C(C 1 -C 2 alkyl) 2 or C(H)(C 1 -C 2 alkoxy);
n1 is 2, 3, 4 or 5; and
n2 and n3 are independently 1, 2 or 3 provided that n2+n3 is 2, 3 or 4;
or R 4 and R 5 taken together are —(CH 2 ) n4 — or —(CH 2 ) n5 —C(R 7a )(R 7b )—(CH 2 ) n6 — or —C(R 7c )═C(R 7d )—;
wherein R 7a is C 1 -C 2 alkyl or C 1 -C 2 alkoxy; and IC′ is hydrogen or C 1 -C 2 alkyl provided that IC′ is hydrogen when R 7a is C 1 -C 2 alkoxy;
n4 is 1, 2 or 3; and
n5 and n6 are independently 0, 1 or 2 provided that n5+n6 is 0, 1 or 2;
and R 7c and R 7d independently are hydrogen or C 1 -C 2 alkyl; and
Y is O, S, S(O), S(O) 2 , N(C 1 -C 2 alkyl), N(C 1 -C 2 alkoxy), C(O), CR 8 R 9 or —CR 10 R 11 CR 12 R 13 —; and
R 8 and R 9 are, independently of each other:
hydrogen, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 2 fluoroalkyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl, C 1 -C 3 alkylthioC 1 -C 3 alkyl, C 1 -C 3 alkylsulfinylC 1 -C 3 alkyl, or C 1 -C 3 alkylsulfonylC 1 -C 3 alkyl; C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one or two substituents which independently are C 1 -C 3 alkyl or C 1 -C 2 fluoroalkyl; and in which one ring CH 2 moiety of a C 4 -C 6 cycloalkyl is optionally replaced by an oxygen or sulfur atom or by a S(O), S(O) 2 , NH, N(C 1 -C 3 alkyl), N(C 1 -C 2 fluoroalkyl), N[C(O)C 1 -C 3 alkyl], N[C(O)C 1 -C 2 fluoroalkyl] or N(C 1 -C 2 alkoxy) moiety;
C 3 -C 6 cycloalkyl substituted by one substituent being C 1 -C 3 alkoxy and optionally further substituted by one substituent being C 1 -C 2 alkyl;
C 5 -C 6 cycloalkenyl or C 5 -C 6 cycloalkenyl substituted by one or two C 1 -C 3 alkyl substituents;
C 3 -C 6 cycloalkylC 1 -C 2 alkyl- or C 3 -C 6 cycloalkylC 1 -C 2 alkyl- substituted by one or two ring substituents which independently are C 1 -C 3 alkyl or C 1 -C 2 fluoroalkyl; and in which one ring CH 2 moiety of a C 4 -C 6 cycloalkylC 1 -C 2 alkyl- is optionally replaced by an oxygen or sulfur atom or by a S(O), S(O) 2 , NH, N(C 1 -C 2 alkyl), N(C 1 -C 2 fluoroalkyl), N[C(O)C 1 -C 3 alkyl], N[C(O)C 1 -C 2 fluoroalkyl] or N(C 1 -C 2 alkoxy) moiety;
C 3 -C 6 cycloalkylC 1 -C 2 alkyl- substituted by one ring substituent being C 1 -C 3 alkoxy and optionally further substituted by one ring substituent being C 1 -C 2 alkyl; or
Het or Het-CH 2 —, wherein Het is a heteroaryl, attached at a ring-carbon, which is optionally substituted by 1, 2 or 3 ring-carbon substituents independently being C 1 -C 3 alkyl, C 1 -C 2 fluoroalkyl, C 1 -C 3 alkyl-C(O)—, C 1 -C 2 fluoroalkyl-C(O)—, hydroxy (including any oxo tautomer), C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkoxy, C 1 -C 2 fluoroalkoxy, halogen, cyano or nitro, provided that any non-fluorine halogen, alkoxy or fluoroalkoxy is not substituted at any ring-carbon bonded directly to a ring-nitrogen of the heteroaryl; and/or, in the case of a 5-membered heteroaryl ring containing a ring-nitrogen atom not partaking in a C═N ring double bond, the heteroaryl is optionally substituted on the ring-nitrogen atom not partaking in a C═N ring double bond by one C 1 -C 3 alkyl, C 1 -C 2 fluoroalkyl, C 1 -C 3 alkyl-C(O)—, C 1 -C 2 fluoroalkyl-C(O)— or C 1 -C 2 alkyl-S(O) 2 — substituent;
provided that no more than one of R 8 and R 9 is an optionally substituted cycloalkyl; an optionally substituted cycloalkyl in which one ring CH 2 moiety has been replaced by an oxygen or sulfur atom or by a S(O), S(O) 2 , NH, N(C 1 -C 3 alkyl), N(C 1 -C 2 fluoroalkyl), N[C(O)C 1 -C 3 alkyl], N[C(O)C 1 -C 2 fluoroalkyl] or N(C 1 -C 2 alkoxy) moiety; an optionally substituted cycloalkenyl; an optionally substituted cycloalkyl-alkyl-; an optionally substituted cycloalkyl-alkyl- in which one ring CH 2 moiety has been replaced by an oxygen or sulfur atom or by a S(O), S(O) 2 , NH, N(C 1 -C 3 alkyl), N(C 1 -C 2 fluoroalkyl), N[C(O)C 1 -C 3 alkyl], N[C(O)C 1 -C 2 fluoroalkyl] or N(C 1 -C 2 alkoxy) moiety; or Het or Het-CH 2 —;
or R 8 is hydrogen or C 1 -C 2 alkyl, and R 9 is C 1 -C 2 alkoxy;
or R 8 and R 9 taken together are —(CH 2 ) n7 — or —(CH 2 ) n8 —X 2 —(CH 2 ) n9 —;
wherein X 2 is O, S, S(O), S(O) 2 , NH, N(C 1 -C 3 alkyl), N(C 1 -C 2 fluoroalkyl), N[C(O)C 1 -C 3 alkyl], N[C(O)C 1 -C 2 fluoroalkyl], N(C 1 -C 2 alkoxy), C(H)(C 1 -C 3 alkyl), C(C 1 -C 2 alkyl) 2 or C(H)(C 1 -C 3 alkoxy);
n7 is 2, 3, 4, 5 or 6; and
n8 and n9 are independently 0, 1, 2 or 3 provided that n8+n9 is 2, 3, 4 or 5; and
R 10 , R 11 , R 12 and R 13 are independently of each other hydrogen or C 1 -C 4 alkyl provided that no more than one of R 10 , R 11 , R 12 and R 13 is C 3 -C 4 alkyl; and
and wherein:
G is hydrogen; or
G is —C(X a )—R a , —C(X b )—X c —R b , —C(X d )—N(R c )—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 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 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

Assignees

• Syngenta Ltd

Inventors

• Mound William Roderick
• Scutt James Nicholas
• Slater Mark
• Willetts Nigel James

Classifications

• A01N35/06

  containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals · CPC title

• C07C49/753

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• A01N43/40

  six-membered rings · CPC title

• A01N43/16 Primary

  with oxygen as the ring hetero atom · CPC title

• A01N37/02

  Saturated carboxylic acids or thio analogues thereof; Derivatives thereof · CPC title