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

Patent metadata

Field	Value
Publication number	US-9808003-B2
Application number	US-201414785470-A
Country	US
Kind code	B2
Filing date	Apr 16, 2014
Priority date	Apr 19, 2013
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

The present invention relates to a compound of formula (I): wherein the 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, ethoxy or fluoromethoxy;
R 2 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, fluoroethyl, vinyl, prop-1-enyl, ethynyl, prop-1-ynyl, 2-chloroethynyl, 2-fluoroethynyl, 2-(trifluoromethyl)ethynyl, but-1-ynyl, 2-(cyclopropyl)ethynyl, halogen, methoxy, prop-2-ynyloxy,
or (C 1 -C 2 fluoroalkyl)-methoxy-;
or R 2 is phenyl optionally substituted by 1, 2 or 3 of, independently, halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, cyano or nitro;
or R 2 is monocyclic heteroaryl optionally substituted by 1, 2 or 3 of independently,halogen, C 1 -C 2 alkyl, C 1 -C 2 fluoroalkyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, cyano or nitro;
or R 2 is

 in which R 36 is fluorine or chlorine, and R 37 is fluorine, chlorine or C 1 fluoroalkyl; and
R 3 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy, n-propoxy, isopropoxy, 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 4 , R 5 and R 6 , 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 4 , R 5 and R 6 are hydrogen, or (ii) two of R 4 , R 5 and R 6 are methyl and the remaining one of R 4 , R 5 and R 6 is hydrogen; and
R 7 and R 8 , independently of each other, are hydrogen, fluorine or C 1 -C 3 alkyl; and
R 9 and R 10 , independently of each other, are hydrogen, fluorine or C 1 -C 3 alkyl;
provided that no more than two of R 7 , R 8 , R 9 and R 10 are fluorine;
and provided that at least two of R 7 , R 8 , R 9 and R 10 are hydrogen;
and wherein
R 11 is C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, tetrahydro-2H-pyranyl, tetrahydrofuranyl, oxetanyl, tetrahydrothiophene-yl or thietanyl;
or R 11 is a monocyclic 6-membered-ring heteroaryl, which is carbon-linked, and which is pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl or 1,2,4-triazinyl, wherein the monocyclic 6-membered-ring heteroarylisoptionally substituted by 1, 2 or 3 substituents;
wherein the 1, 2 or 3 optional substituents on the monocyclic 6-membered-ring heteroaryl independently are fluorine, chlorine, bromine, iodine, C 1 -C 3 alkyl, C 1 -C 3 fluoro alkyl, C 1 -C 2 alkoxy C 1 -C 2 fluoroalkoxy, cyclopropyl, C n1 alkoxyC n2 alkyl (wherein n1 is 1 or 2, n2 is 1 or 2, and n1+n2 is 2 or 3), vinyl, C 2 fluoroalkenyl, C 2 -C 3 alkynyl, fluoroethynyl, cyano, amino, or phenyl in which the phenyl is optionally substituted at its meta and/or para position(s) by 1 or 2 fluorines; and

wherein, when R 11 is pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl or 1,2,4-triazinyl, then each of these is optionally substituted by 1 or 2 of the substituents on the monocyclic 6-membered-ring heteroaryl, as defined herein;
wherein, when R 11 is pyridin-3-yl or pyridin-4-yl, then each of these is substituted by 1 or 2 of the substituents on the monocyclic 6-membered-ring heteroaryl, as defined herein,

wherein, when R 11 is pyridin-2-yl substituted by 3 substituents, then one or more of the optional substituents on the pyridin-2-yl is or are fluorine;
wherein, when R 11 is monocyclic 6-membered-ring heteroaryl substituted by C 2 alkyl, C 2 fluoroalkyl, C 2 alkoxy or C 2 fluoroalkoxy, then: the monocyclic 6-membered-ring heteroaryl is substituted by 1 or 2 substituents independently being C 2 alkyl, C 2 fluoroalkyl, C 2 alkoxy or C 2 fluoroalkoxy, and the monocyclic 6-membered-ring heteroaryl is optionally further substituted by 1 or 2 substituents independently being fluorine, chlorine, bromine, C 1 alkyl, C 1 fluoroalkyl, C 1 alkoxy, C 1 fluoroalkoxy or cyano; provided that the monocyclic 6-membered-ring heteroaryl is substituted by no more than 2 substituents or in the case of a pyridin-2-yl is substituted by no more than 3 substituents;
wherein, when R 11 is monocyclic 6-membered-ring heteroaryl substituted by iodine, C 3 alkyl, C 3 fluoroalkyl, cyclopropyl, C n1 alkoxyC n2 alkyl, vinyl, C 2 fluoroalkenyl, C 2 -C 3 alkynyl or fluoroethynyl, then: the monocyclic 6-membered-ring heteroaryl is pyridin-2-yl substituted by only one iodine, C 3 alkyl, C 3 fluoroalkyl, cyclopropyl, C n1 alkoxyC n2 alkyl, vinyl, C 2 fluoroalkenyl, C 2 -C 3 alkynyl or fluoroethynyl, and in which the pyridin-2-yl ring is optionally further substituted by 1 or 2 fluorines;
wherein, when R 11 is monocyclic 6-membered-ring heteroaryl substituted by amino, then: either the monocyclic 6-membered-ring heteroaryl is 6-amino-pyridin-2-yl optionally further substituted by 1 or 2 fluorines; or the monocyclic 6-membered-ring heteroaryl is 3-amino-pyridin-2-yl or 3-amino-pyrazin-2-yl each of which is optionally further substituted at the 5-position of the pyridin-2-yl or pyrazin-2-yl ring by hydrogen, fluorine, methyl or C 1 fluoroalkyl; and
wherein, when R 11 is monocyclic 6-membered-ring heteroaryl substituted by optionally substituted phenyl, then the monocyclic 6-membered-ring heteroaryl is 6-phenyl-pyridin-2-yl in which the phenyl is optionally substituted at its meta and/or para position(s) by 1 or 2 fluorines, and in which the pyridin-2-yl ring is optionally further substituted by 1 or 2 fluorines;
or R 11 is a monocyclic 5-membered-ring heteroaryl, which is carbon-linked, and which is pyrrolyl, pyrazolyl, imidazol-2-yl, triazolyl, tetrazolyl, furyl, thiophenyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, or thiadiazolyl, wherein the monocyclic 5-membered-ring heteroaryl is optionally substituted by 1, 2 or 3 substituents;
wherein the 1, 2 or 3 optional substituents on the monocyclic 5-membered-ring heteroaryl are:
1, 2 or 3 optional ring-carbon substituents independently being fluorine, chlorine, bromine, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, cyclopropyl, C n3 alkoxyC n4 alkyl (wherein n3 is 1 or 2, n4 is 1 or 2, and n3+n4 is 2 or 3), vinyl, C 2 fluoroalkenyl, C 2 -C 3 alkynyl, fluoroethynyl or cyano; and/or
1 substituent being C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl or cyclopropyl, substituted at a ring nitrogen not partaking in a double bond, when the monocyclic 5-membered-ring heteroaryl has a ring nitrogen not partaking in a double bond;
provided that the monocyclic 5-membered-ring heteroaryl has no more than 3 substituents, or has no more than the maximum number of substituents possible for the monocyclic 5-membered-ring heteroaryl in uncharged form if this maximum is less than 3 substituents; and

wherein, when R 11 is a monocyclic 5-membered-ring heteroaryl having a ring nitrogen not partaking in a double bond, then the ring nitrogen not partaking in a double bond is substituted by C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl or cyclopropyl; and
wherein, when R 11 is a monocyclic 5-membered-ring heteroaryl, then: the monocyclic 5-membered-ring heteroaryl has no more than one C 3 fluoroalkyl, vinyl, C 2 fluoroalkenyl, C 2 -C 3 alkynyl or fluoroethynyl substituent; the monocyclic 5-membered-ring heteroaryl has no more than 2 substituents independently being bromine, C 2 -C 3 alkyl, C 2 -C 3 fluoroalkyl, C 1 -C 2 alkoxy, C 1 -C 2 fluoroalkoxy, cyclopropyl, C n3 alkoxyC n4 alkyl, vinyl, C 2 fluoroalkenyl, C 2 -C 3 alkynyl, fluoro

Assignees

• Syngenta Ltd

Inventors

• Avery Alaric James
• Taylor John Benjamin
• Viner Russell Colin
• Wailes Jeffery Steven
• Cloudsdale Ian Stuart
• Dickson Jr John Kenneth
• Aspinall Ian Henry
• Black Janice
• Briggs Emma
• Hachisu Shuji
• Hardy Simon

Classifications

• C07D213/82

  in position 3 · CPC title

• A01N43/52

  condensed with carbocyclic rings, e.g. benzimidazoles · CPC title

• C07D231/14

  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 carbon atoms · CPC title

• C07D237/24

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• C07C233/31

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom · CPC title