The present invention relates to herbicidally active cyclic diones, in particular pyrandione,
thiopyrandione, cyclohexanedione, alkanediyl-bridged cyclohexanedione, cyclohexanetrione
or cycloheptanedione compounds, or derivatives thereof (e.g. enol ketone tautomer
derivatives thereof), to processes for their preparation, to herbicidal compositions comprising
those compounds, and to their use in controlling weeds such as grassy monocotyledonous
weeds, especially in crops of useful plants, or in inhibiting undesired plant growth. In
particular, the present invention relates to herbicidally active cyclic dione compounds, or
derivatives thereof (e.g. enol ketone tautomer derivatives thereof), which are substituted by a
phenyl which has an alkynyl-containing substituent.
WO 01/17972 A2 (Syngenta Participations AG) discloses phenyl-substituted (such as
4-methyl-2,6-diethyl-phenyl- substituted) heterocycles suitable for use as herbicides.
WO 03/013249 A 1 (Bayer AG) and its equivalent US 2005/0054535 A 1 disclose selective
herbicidal compositions comprising (a) a (substituted-phenyl)-substituted cyclic ketoenol and
(b) a compound which improves crop plant compatibility, in particular cloquintocet-mexyl or
mefenpyr-diethyl.
WO 2007/068427 A2 (Bayer CropScience AG) and its equivalent US 2009/0227563 A 1
disclose a composition comprising (a) a (substituted-phenyl)-substituted cyclic ketoenol as a
herbicide, and (b) an ammonium or phosphonium salt to boost activity.
WO 2008/071405 A 1 and WO 2009/074314 A 1 (both Syngenta Limited and Syngenta
Participations AG) each disclose herbicidally active pyran-3,5-diones, thiopyran-3,5-diones
and cyclohexane-1 ,3,5-triones, each substituted at the 4-position of the cyclic dione or trione
by an aryl-substituted-phenyl or by a heteroaryl-substituted-phenyl.
WO 2010/081755 A 1 and WO 2010/08921 1 A 1 (both Syngenta Limited) each disclose
herbicidally active pyran-3,5-diones, thiopyran-3,5-diones, cyclohexanediones,
cycloheptanediones and cyclohexanetriones, each substituted by an aryloxy-substitutedphenyl
or by a heteroaryloxy-substituted-phenyl.
WO 2008/1 10308 A 1 (Syngenta Participations AG) discloses 2-(substituted-phenyl)-
cyclohexane-1 ,3-dione compounds and derivatives, containing a R -X-(CR6R7)n- substituent
(wherein X is O, S, S(O) or S(0) 2) or a heteroatom-containing-spirocyle at the 5-position of
the cyclohexane-1 ,3-dione, and having herbicidal properties. WO 2008/1 10307 A 1
(Syngenta Participations AG) discloses 2-(substituted-phenyl)-5-heterocyclyl-cyclohexane-
1,3-dione compounds and derivatives, and their use as herbicides. WO 2010/046194 A 1
(Syngenta Limited) discloses 2-(substituted-phenyl)-cyclohexane-1 ,3-dione compounds and
derivatives, containing a Q-CR6R7- substituent at the 5-position of the cyclohexane-1 ,3-dione
(wherein Q is a saturated or mono-unsaturated heterocycle), and having herbicidal
properties.
WO 2008/145336 A 1 and A8 (Syngenta Limited) disclose herbicidally active phenylsubstituted
bicyclic (carbon-bridged, e.g. alkanediyl-bridged) 1,3-dione compounds, such as
3-(substituted-phenyl)-bicyclo[3.2.1]octane-2,4-diones.
Copending PCT application PCT/EP201 2/0741 18, filed on 30 November 2012 and published
on 6 June 2013 as WO 2013/079672 A 1 (Syngenta Limited and Syngenta Participations AG)
discloses that certain substituted spiroheterocyclic pyrrolidine dione compounds, having an
alkynyl-phenyl- headgroup, have herbicidal properties.
Copending PCT application PCT/EP201 2/0741 72, filed on 30 November 2012 and published
on 6 June 2013 as WO 2013/079708 A 1 (Syngenta Limited and Syngenta Participations AG)
discloses cyclopentane-1 ,3-dione compounds and derivatives (e.g. fused and/or spirocyclic
bicyclic derivatives) thereof, which are substituted at the 2-position of the cyclopentane-1 ,3-
dione by a phenyl which itself is substituted at the 4-position by (specifically) either
prop-1-ynyl or chloroethynyl, and derivatives of the enol ketone tautomer of such
cyclopentanediones, which have herbicidal activity and/or plant-growth-inhibiting properties,
especially in the control of grassy monocotyledonous weeds and/or when used postemergence.
Cyclic dione compounds have now been found, in particular pyran-3,5-dione, thiopyran-3,5-
dione, cyclohexane-1 ,3-dione, alkanediyl-bridged cyclohexane-1 ,3-dione, cyclohexane-1 ,3,5-
trione or cycloheptane-1 ,3-dione compounds, which are substituted, at the ring-carbon atom
of the cyclic dione which is between the two oxo-substituted ring-carbons of the cyclic dione,
by a phenyl which itself is substituted at the 4-position by (specifically) either prop-1-ynyl or
chloroethynyl and at the 2-position by (specifically) methyl or chlorine, or derivatives of the
enol ketone tautomer of such cyclic diones, which have herbicidal activity and/or plantgrowth-
inhibiting properties, in particular in the control of grassy monocotyledonous weeds.
The herbicidal data available, as shown in the Biological Examples hereinafter, suggests that
these 4-(prop-1-ynyl)-2-(methyl or chloro)-phenyl or 4-(chloroethynyl)-2-(methyl or chloro)-
phenyl cyclic dione compounds are more potent herbicides against grassy
monocotyledonous weeds (e.g. when applied post-emergence) than the corresponding 4-
ethynyl-2-(methyl or chloro)-phenyl cyclic dione compounds. The herbicidal activity against
"warm-season" (warm climate) grassy monocotyledonous weeds of most of the compounds
of the invention which have been exemplified and tested herein (compounds A-1 to A-17,
A-1 8 to A-24, P-1 to P-5, or P-7) appears to be potent, in particular after post-emergence
application of the compounds at an application rate of about 250 g/ha. Also, many of the
exemplified compounds exhibit a reasonably low phytotoxicity against wheat and/or certain
docotyledonous crops, in particular soybean and/or sugar beet (see Biological Examples 1B
and 3 hereinafter).
Therefore, in a first aspect of the present invention, there is provided a compound of formula
(I):
wherein:
X is methyl or chlorine;
R is methyl or chlorine;
R2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine,
CrCsalkoxy, C1-C2fluoroalkoxy, C1-C2alkoxy-C 1-C3alkoxy-, or dfluoroalkoxy-CrCsalkoxy-;
and
R3, R4, R5 and R6, independently of each other, are hydrogen, C -C5alkyl (in particular C
C4alkyl, e.g. C C2alkyl), C2-C4alkenyl (in particular C2-C3alkenyl-CH2- , e.g. ethenyl-CH 2-),
C2-C4alkynyl (in particular C2-C3alkynyl-CH2- , e.g. ethynyl-CH2-), C C2fluoroalkyl,
Ci-C 3alkoxyCi-C 3alkyl, Ci-C 3alkylthioCi-C 3alkyl, Ci-C 3alkylsulfinylCi-C 3alkyl,
Ci-C 3alkylsulfonylCi-C 3alkyl; C3-C4cycloalkyl (in particular cyclopropyl); or an unsubstituted
4, 5 or 6 (e.g. 4 or 5) membered monocyclic heterocyclyl having one ring heteroatom
independently selected from oxygen, sulfur and nitrogen, and attached at a ring carbon atom
within the heterocyclyl (in particular tetrahydrofuranyl such as tetrahydrofuran-3-yl, or
tetrahydropyranyl such as tetrahydropyran-4-yl);
provided that no more than one (in particular none) of R3, R4, R5 and R6 is alkenyl, alkynyl,
alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
or R3 and R4 taken together are -(CH2)nr or -(CH2 )n2 -X -(CH2 )n3- and R5 and R6 are as
defined herein (e.g. hereinabove), or R5 and R6 taken together
are -(CH2)ni- or -(CH2) 2-X -(CH2) 3- and R3 and R4 are as defined herein (e.g. hereinabove);
wherein X1 is O, S, S(O), S(0) 2, NH, N(C C2alkyl), N(C C2alkoxy), C(H)(C C2alkyl),
C(C C2alkyl)2 or C(H)(C C2alkoxy);
n 1 is 2, 3, 4 or 5 (in particular 4 or 5); and
n2 and n3 are independently 1, 2 or 3 provided that n2 + n3 is 2, 3 or 4 (in particular 3 or 4);
or R4 and R5 taken together are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- or -C(R7 )=C(R7 )-;
wherein R7a is CrC 2alkyl or Ci-C 2alkoxy; and R7 is hydrogen or Ci-C 2alkyl provided that R7
is hydrogen when R7a is C -C2alkoxy;
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 R7 and R7 independently are hydrogen or C -C2alkyl; and
Y is O, S, S(O), S(0) 2, N(C C2alkyl), N(C C2alkoxy), C(O), CR R or -CR 0R CR 2R13- ; and
R8 and R are, independently of each other:
hydrogen, -C6alkyl (in particular CrC 4alkyl, e.g. Ci-C 2alkyl), C2-C4alkenyl (in
particular C2-C3alkenyl-CH 2- , e.g. ethenyl-CH 2-), C2-C4alkynyl (in particular
C2-C3alkynyl-CH 2- , e.g. ethynyl-CH 2-), C C2fluoroalkyl, Ci-C 3alkoxyC C3alkyl,
Ci-C 3alkylthioC C3alkyl, Ci-C 3alkylsulfinylC C3alkyl, or Ci-C 3alkylsulfonylC C3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are CrC 3alkyl (in particular methyl or ethyl) or Ci-C 2fluoroalkyl; and in which
one ring CH2 moiety of a C4-C6cycloalkyl is optionally (e.g. preferably) replaced by an oxygen
or sulfur atom or by a S(O), S(0) 2, NH, N(CrC 3alkyl), N(CrC 2fluoroalkyl), N[C(0)CrC 3alkyl],
N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being -C3alkoxy (in particular
CrC 2alkoxy) and optionally further substituted by one substituent being C -C2alkyl (in
particular methyl);
C5-C6cycloalkenyl or C5-C6cycloalkenyl substituted by one or two CrC 3alkyl (in
particular methyl) substituents;
C3-C6cycloalkylCrC 2alkyl- (in particular C3-C6cycloalkylmethyl-) or C3-C6cycloalkylCr
C2alkyl- (in particular C3-C6cycloalkylmethyl-) substituted by one or two ring substituents
which independently are CrC 3alkyl or C -C2fluoroalkyl; and in which one ring CH2 moiety of a
C4-C6cycloalkylC 1-C2alkyl- (in particular C4-C6cycloalkylmethyl-) is optionally (e.g. preferably)
replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C1-C2alkyl), N(C
C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety;
Cs-CecycloalkylCrC^alkyl- (in particular C3-C6cycloalkylmethyl-) substituted by one ring
substituent being Ci -C3alkoxy (in particular Ci -C2alkoxy) and optionally further substituted by
one ring substituent being C -C2alkyl (in particular methyl); or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon , which is
optionally substituted by 1, 2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents
independently being C -C3alkyl (e.g. C -C2alkyl), C -C2fluoroalkyl, C -C3alkyl-C(0)-,
C -C2fluoroalkyl-C(0)-, hydroxy (including any oxo tautomer), C2-C3alkenyl (e.g. ethenyl or
prop-1 -enyl), C2-C3alkynyl (e.g. ethynyl or prop-1 -ynyl), -C3alkoxy (e.g. CrCsalkoxy), C
C2fluoroalkoxy, halogen (e.g. fluorine or chlorine), cyano or nitro, provided that any nonfluorine
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 C3alkyl, C C2fluoroalkyl , C C3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or
C -C2alkyl-S(0) 2- substituent;
provided that no more than one of R8 and R is an optionally substituted cycloalkyl; an
optionally substituted cycloalkyl in which one ring CH2 moiety has been replaced by an
oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl),
N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety; an optionally
substituted cycloalkenyl ; an optionally substituted cycloalkyl-alkyl-; an optionally substituted
cycloalkyl-alkyl- in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom
or by a S(O), S(0) 2, NH, N(CrC3alkyl), N(C C2fluoroalkyl), N[C (0 )CrC3alkyl],
N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety; or Het or Het-CH2- ;
or R8 is hydrogen or C -C2alkyl (in particular H or Me), and R is CrC 2alkoxy (in particular
methoxy);
or R8 and R9 taken together are -(CH2) 7- or -(CH2) 8-X2-(CH2) 9- ;
wherein X2 is O, S, S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0 )CrC2fluoroalkyl], N(C C2alkoxy), C(H)(C C3alkyl), C(C C2alkyl)2 or
C(H)(Ci -C3alkoxy);
n7 is 2, 3, 4, 5 or 6 (in particular 4 or 5); and
n8 and n9 are independently 0, 1, 2 or 3 provided that n8 + n9 is 2, 3, 4 or 5 (in particular 3
or 4); and
R 0 , R , R 2 and R 3 are independently of each other hydrogen or CrC 4alkyl (in particular
C -C2alkyl) provided that no more than one of R 0 , R , R 2 and R 3 is C3-C4alkyl; and
and wherein:
G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or
ammonium group; or
G is -C(Xa)-Ra, -C(X )-X -R , -C(X )-N(R )-R , -S0 2-Re, -P(Xe)(R )-R9, -CH2-X -Rh; or
phenyl-CH2- or phenyl-CH(C -C2alkyl)- (in each of which the phenyl is optionally substituted
by 1, 2 or 3 of, independently, Ci-C 2alkyl, CifluoroalkyI, Ci-C 2alkoxy, Cifluoroalkoxy, fluorine,
chlorine, bromine, cyano or nitro), or heteroaryl-CH 2- or heteroaryl-CH(Ci-C 2alkyl)- (in each
of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, Ci-C 2alkyl,
CifluoroalkyI, Ci-C 2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or
phenyl-C(0)-CH 2- (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently,
CrC 2alkyl, CifluoroalkyI, Ci-C 2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or
nitro); or CrC 6alkoxy-C(0)-CH 2- , CrC 6alkoxy-C(0)-CH=CH-, C2-C7alken-1-yl-CH 2- ,
C2-C7alken-1-yl-CH(C C2alkyl)-, C2-C4fluoroalken-1-yl-CH 2- , C2-C7alkyn-1-yl-CH 2- , or
C2-C7alkyn-1-yl-CH (CrC2alkyl)-;
wherein Xa, X , X , X , Xe and X are independently of each other oxygen or sulfur ( in
particular oxygen); and wherein
Ra is H, Ci-C2ialkyl, C2-C2ialkenyl, C2-Ci 8alkynyl, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d -
C 0nitroalkyl, Ci-Ci 0aminoalkyl, Ci-C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino(Ci-C 5)alkyl,
C 3-C7cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C 5)alkyl, C 3-C5alkenyloxy(Ci-C5)alkyl, C3-
C5alkynyloxy (CrC 5)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, Ci-C5alkylsulfinyl(Ci-C 5)alkyl, Cr
C5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(Ci-C 5)alkyl, d -
dalkylaminocarbonyl(Ci-d)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl, d -
C5alkylcarbonylamino(d-C 5)alkyl, /V-(C1-d)alkylcarbonyl-/V-(C 1-d)alkylamino(C 1-d)alkyl,
d-dtrialkylsilyl(C -d)alkyl, phenyl(C -d)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy,
d-dalkylthio, Ci-C3alkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(dd)
alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, Crdalkylthio, d-C 3alkylsulfinyl,
CrC 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, Ci-C3alkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
of, independently, d-C 3 alkyl, d-C 3fluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen,
cyano or nitro;
R is d-C 18alkyl, C3-C18alkenyl, C3-C18alkynyl, C2-C10fluoroalkyl, d-C 10cyanoalkyl, d -
C10nitroalkyl, C2-C10aminoalkyl, CrC 5alkylamino(CrC 5)alkyl, C2-C8dialkylamino(CrC 5)alkyl,
C3-C7cycloalkyl(CrC 5)alkyl, Ci-C5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-
C5alkynyloxy(Ci-C 5)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, Ci-C5alkylsulfinyl(Ci-C 5)alkyl, d -
C5alkylsulfonyl(CrC 5)alkyl, C2-C8alkylideneaminoxy(CrC 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, Ci-C5alkoxycarbonyl(CrC 5)alkyl, aminocarbonyl(CrC 5)alkyl, d -
C5alkylaminocarbonyl(CrC 5)alkyl, C2-C8dialkylaminocarbonyl(CrC 5)alkyl, d -
C5alkylcarbonylamino(CrC 5)alkyl, /V-(Ci-C5)alkylcarbonyl-/\/-(CrC 5)alkylamino(CrC 5)alkyl,
C3-C6trialkylsilyl(CrC 5)alkyl, phenyl(d-C 5)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, Ci-C3alkoxy, Crdfluoroalkoxy,
d-dalkylthio, d-C 3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryld-
C5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, Crdfluoroalkyl, d-dalkoxy, CrCsfluoroalkoxy, d-C 3alkyl-thio, d-dalkylsulfinyl,
CrC 3alkylsulfonyl, halogen, cyano, or nitro), C3-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, CrC 3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
of, independently, C C3 alkyl, CrC 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen,
cyano or nitro; and
R and R are each independently of each other hydrogen, CrCi 0alkyl, C3-Ci 0alkenyl, C3-
C 0alkynyl, C2-Ci 0fluoroalkyl, Ci-Ciocyanoalkyl, Ci-Ci 0nitroalkyl, Ci-Ci 0aminoalkyl, d -
C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino (Ci-C 5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl, Cr
C5alkoxy(d-C5)alkyl, C3-C5alkenyloxy (d-C 5)alkyl, C3-C5alkynyloxy (d-C 5)alkyl, C
C5alkylthio(d-C5)alkyl, C1-C5alkylsulfinyl(C 1-C5)alkyl, C1-C5alkylsulfonyl(C 1-C5)alkyl, C2-
C8alkylideneaminoxy(C 1-C5)alkyl, C1-C5alkylcarbonyl(C 1-C5)alkyl, CrC 5alkoxycarbonyl(Cr
C5)alkyl, aminocarbonyl(d-C 5)alkyl, C1-C5alkylaminocarbonyl(C 1-C5)alkyl, C2-
C8dialkylaminocarbonyl(C -C5)alkyl, C -C5alkylcarbonylamino(C -C5)alkyl, /V-(d-
C5)alkylcarbonyl-/V-(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(C 1-C5)alkyl, phenyl(d-C 5)alkyl
(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
C3fluoroalkyl, Ci-C3alkoxy, Ci-C 3fluoroalkoxy, Ci-C3alkylthio, Ci-C 3alkylsulfinyl, d -
C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(Ci-C 5)alkyl (wherein the heteroaryl is
optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d -
C3alkoxy, CrCsfluoroalkoxy, CrC 3alkylthio, d-C 3alkylsulfinyl, d-C 3alkylsulfonyl, halogen,
cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, CrC 3fluoroalkoxy, halogen,
cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d-C 3alkyl,
Crdfluoroalkyl, d-C 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
heteroarylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl, Crdfluoroalkyl, d -
dalkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
substituted by 1, 2 or 3 of, independently, d-C 3alkyl, Crdfluoroalkyl, d-C 3alkoxy, d -
C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
of, independently, d-C 3alkyl, Crdfluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, halogen,
cyano or by nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently,
d-dalkyl, Crdfluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; or C3-
dcycloalkylamino, di(C3-C7cycloalkyl)amino or C3-C7cycloalkoxy;
or R and R , 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
Re is Ci-Ci 0alkyl, C2-Ci 0alkenyl, C2-Ci 0alkynyl, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d -
C 0nitroalkyl, Ci-Ci 0aminoalkyl, Ci-C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino(Ci-C 5)alkyl,
C3-C7cycloalkyl(Ci-C 5)alkyl, Ci-C 5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(Ci-C 5)alkyl, C3-
C5alkynyloxy(Ci-C 5)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, Ci-C 5alkylsulfinyl(Ci-C 5)alkyl, d -
C5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, Ci-C 5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(Ci-C 5)alkyl, d -
C5alkylaminocarbonyl(C 1-C5)alkyl, C2-C8dialkylaminocarbonyl(C 1-C5)alkyl, d -
C5alkylcarbonylamino(C 1-C5)alkyl, /V-(C1 -C5 )alkylcarbonyl-/V-(C1-C5)alkylamino(C1-C5)alkyl,
C3-C6trialkylsilyl(C -C5)alkyl, phenyl(C -C5)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, Ci-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy, Crdfluoroalkoxy,
d-dalkylthio, d-dalkylsulfinyl, C -C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(d-
C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-dfluoroalkyl, d-dalkoxy, d-C 3fluoroalkoxy, d-dalkylthio, Ci-C 3alkylsulfinyl,
d-dalkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy,
d-C 3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of,
independently, d-C 3alkyl, Ci-C3fluoroalkyl, d-dalkoxy, d-C 3fluoroalkoxy, halogen, cyano
or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, d-d
alkyl, d-C 3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, d-dalkyl,
d-dfluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; phenylamino or
phenylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d -
dalkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino
substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy, d -
C3fluoroalkoxy, halogen, cyano or nitro; or d-dcycloalkylamino, di(C3-C7cycloalkyl)amino,
C3-C7cycloalkoxy, d-Ci 0alkoxy, d-Ciofluoroalkoxy, d-C 5alkylamino or di(Ci-C 4alkyl)amino;
R and R9 are are each independently of each other Ci-Cioalkyl, C2-Ci 0alkenyl, C2-Ci 0alkynyl,
d-Cioalkoxy, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d-Ci 0nitroalkyl, d-Cioaminoalkyl, d -
C5alkylamino(CrC 5)alkyl, C2-C8dialkylamino(CrC 5)alkyl, C3-C7cycloalkyl(CrC 5)alkyl, Cr
C5alkoxy(C1-C5)alkyl, C 3-C5alkenyloxy(C1-C5)alkyl C 3-C5alkynyloxy(C1-C5)alkyl C
C5alkylthio(Ci-C 5)alkyl, C1-C5alkylsulfinyl(C -C5)alkyl, Ci-C5alkylsulfonyl(Ci-C 5)alkyl, C2-
C8alkylideneaminoxy(Ci-C 5)alkyl, Ci-C5alkylcarbonyl(Ci-C 5)alkyl, Ci-C5alkoxycarbonyl(Ci-
C5)alkyl, aminocarbonyl(CrC 5)alkyl, Ci-C5alkylaminocarbonyl(Ci-C 5)alkyl, C2-
C8dialkylaminocarbonyl(Ci-C 5)alkyl, Ci-C5alkylcarbonylamino(Ci-C 5)alkyl, /V-(d-
C 5)alkylcarbonyl-/V-(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl (Ci-C 5)alkyl, phenyl(C C5)alkyl
(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, CrC 3alkyl, d -
C3fluoroalkyl, CrC 3alkoxy, Ci-C 3fluoroalkoxy, Ci-C3alkylthio, CrC 3alkylsulfinyl, d -
C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(Ci-C 5)alkyl (wherein the heteroaryl is
optionally substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, d -
dalkoxy, Crdfluoroalkoxy, d-C 3alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen,
cyano, or nitro), C2-dfluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
of, independently, d-dalkyl, d-C 3fluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen,
cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d-d alkyl,
d-dfluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
heteroarylamino substituted by 1, 2 or 3 of, independently, d-C 3 alkyl, d-C 3fluoroalkyl, d -
dalkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
substituted by 1, 2 or 3 of, independently, Ci-C 3 alkyl, d-C 3fluoroalkyl, Crdalkoxy, Ci-
Csfluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
of, independently, d-dalkyl, d-dfluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen,
cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-dfluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; or C3-
dcycloalkylamino, di(C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, d-C 10fluoroalkoxy, d -
dalkylamino or di(CrC 4alkyl)amino; or benzyloxy or phenoxy, wherein the benzyl and
phenyl groups are in turn optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
dfluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; and
Rh is d-Cioalkyl, C3-Ci 0alkenyl, C3-Ci 0alkynyl, d-Ci 0fluoroalkyl, d-Ciocyanoalkyl, d -
Cionitroalkyl, C2-Ci 0aminoalkyl, Ci-C5alkylamino(CrC 5)alkyl, C2-C8dialkylamino(CrC 5)alkyl,
C3-C7cycloalkyl(CrC 5)alkyl, Ci-C 5alkoxy(CrC 5)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-
C5alkynyloxy(CrC 5)alkyl, Ci-C5alkylthio(CrC 5)alkyl, Ci-C 5alkylsulfinyl(CrC 5)alkyl, Cr
C5alkylsulfonyl(CrC 5)alkyl, C2-C8alkylideneaminoxy(CrC 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, Ci-C 5alkoxycarbonyl(CrC 5)alkyl, aminocarbonyl(Ci-C 5)alkyl, d -
C5alkylaminocarbonyl(CrC 5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl, d -
C5alkylcarbonylamino(C -C5)alkyl, /V-(C -C5 )alkylcarbonyl-/V-(C -C5)alkylamino(C -C5)alkyl,
C3-C6trialkylsilyl(Ci-C 5)alkyl, phenyl(CrC 5)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, -C3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, C -C3fluoroalkoxy,
C -C3alkylthio, CrC 3alkylsulfinyl, C C3 alkylsulfonyl, halogen, cyano or nitro), heteroaryl(Ci-
C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, C -C3fluoroalkyl, C -C3alkoxy, C -C3fluoroalkoxy, C -C3alkylthio, CrC 3alkylsulfinyl,
Ci-C 3 alkylsulfonyl, halogen, cyano or nitro), phenoxy(CrC 5)alkyl (wherein the phenyl is
optionally substituted by 1, 2 or 3 of, independently, C -C3alkyl, C -C3fluoroalkyl, d -
C3alkoxy, C -C3fluoroalkoxy, C -C3alkylthio, CrC 3alkylsulfinyl, C C3 alkylsulfonyl, halogen,
cyano or nitro), heteroaryloxy(Ci-C 5)alkyl (wherein the heteroaryl is optionally substituted by
1, 2 or 3 of, independently, C -C3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, d -
C3alkylthio, Ci-C 3alkylsulfinyl, Ci-C 3 alkylsulfonyl, halogen, cyano or nitro), C3-
C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently,
C -C3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro;
heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
C3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro; d-C 6alkyl-C(0)-; or
phenyl-C(O)- wherein the phenyl is optionally substituted by 1 or 2 of, independently, d -
dalkyl, CifluoroalkyI, d-C 2alkoxy, Cifluoroalkoxy, 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 (e.g. where chemically
possible) as an agrochemically acceptable salt thereof.
In the substituent definitions of the compounds of the formula I , each alkyl moiety either
alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl, alkylcarbonyl,
alkylaminocarbonyl, or dialkylaminocarbonyl, et al.) can be straight-chained or branched.
Typically, the alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl,
isobutyl, ie/f-butyl, n-pentyl, neopentyl, or n-hexyl. The alkyl groups can e.g. be Ci-C 6alkyl
groups (except where already defined more narrowly), but are preferably d-C 4alkyl or d -
C3alkyl groups (except where already defined more narrowly), and, more preferably, are
CrC 2alkyl groups such as methyl.
Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the
alkenyl moieties, where appropriate, can be of either the (£)- or (Z)-configuration. The
alkenyl or alkynyl are typically C2-C3alkenyl or C2-C3alkynyl such as vinyl, allyl, ethynyl,
propargyl or prop-1-ynyl. Alkenyl and alkynyl moieties can contain one or more double
and/or triple bonds in any combination; but preferably contain only one double bond (for
alkenyl) or only one triple bond (for alkynyl).
Halogen is fluorine, chlorine, bromine or iodine. Preferred halogens are fluorine, chlorine or
bromine.
FluoroalkyI groups are alkyl groups which are substituted with one or more (e.g. 1, 2, 3, 4 or
5; in particular 1, 2 or 3; e.g. 1 or 2) fluorine atoms. FluoroalkyI is typically C -C3fluoroalkyl or
-C2fluoroalkyl (preferably dfluoroalkyl), such as CF3, CHF2, CH2F, CH3CHF-, CF3CH2- ,
CHF2CH2- , CH2FCH2- , CHF2CF2- or (CH3)2CF-. Fluoroalkoxy is typically C C3fluoroalkoxy
or Ci-C 2fluoroalkoxy (preferably Cifluoroalkoxy), such as CF30 , CHF20 , CH2FO, CH3CHFO-,
CF3CH20-, CHF2CH20 - or CH2FCH20-.
In the context of the present specification the term "aryl" means phenyl or naphthyl. A
preferred aryl group is phenyl.
The term "heteroaryl" as used herein means an aromatic ring system containing at least one
ring heteroatom and consisting either of a single ring or of two fused rings. Preferably, single
rings will contain 1, 2 or 3 ring heteroatoms and bicyclic systems 1, 2, 3 or 4 ring
heteroatoms which will preferably be selected from nitrogen, oxygen and sulfur. Typically, a
"heteroaryl" is furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl,
oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,
1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl,
pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,
benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl,
benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1 ,3-
benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl,
naphthyridinyl, benzotriazinyl, purinyl, pteridinyl or indolizinyl; optionally present, where
chemically possible, as an agrochemically acceptable salt thereof.
The term "heterocyclyl" as used herein, except where explicitly stated otherwise, means a 4,
5, 6 or 7 (in particular 5, 6 or 7) membered monocyclic organic ring or a 8, 9, 10 or 11 (in
particular 8, 9 or 10) membered fused bicyclic organic ring system, which is fully saturated,
and which has one or two (preferably one) ring heteroatoms independently selected from
oxygen, sulfur and nitrogen. Where the heterocyclyl has two ring heteroatoms, preferably,
the two ring heteroatoms are separated by at least two ring carbon atoms. Preferably, the
heterocyclyl is attached at a ring carbon atom within the heterocyclyl. In particular, the
heterocyclyl can be tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, 1,4-dioxanyl,
1,4-dithianyl, morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl or piperazinyl; more
particularly tetrahydrofuranyl (e.g. tetrahydrofuran-2-yl or particularly tetrahydrofuran-3-yl),
tetrahydropyranyl (e.g. tetrahydropyran-2-yl, tetrahydropyran-3-yl or particularly
tetrahydropyran-4-yl), morpholinyl, pyrrolidinyl (e.g. pyrrolidin-2-yl or particularly pyrrolidin-3-
yl), piperidinyl (e.g. piperidin-2-yl, piperidin-3-yl or particularly piperidin-4-yl) or piperazinyl. In
a particular embodiment, the heterocyclyl, when optionally substituted, is optionally
substituted by 1 or 2 (e.g. 1) ring-carbon substituents independently being CrC 3alkyl (e.g.
C1-C2alkyl), C1-C2fluoroalkyl or oxo (=0), and/or is optionally substituted by one CrCsalkyl
(e.g. C1-C2alkyl), C1-C2fluoroalkyl or d-Csalkoxy (e.g. CrC 2alkyl or d-C^luoroalkyl)
substituent on a ring nitrogen if present, and/or is optionally substituted by one or two oxo
(=0) substituents on a ring sulfur if present.
Preferably, a cycloalkyi is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. (Cycloalkyl)alkyl
is preferably (cycloalkyl)methyl such as (C3-C6cycloalkyl)methyl in particular
cyclopropylmethyl. Preferably, cycloalkenyl is cyclopentenyl or cyclohexenyl.
The invention relates also to the agriculturally acceptable salts which the compounds of
formula I are able to form with transition metal, alkali metal and alkaline earth metal bases,
amines, quaternary ammonium bases or tertiary sulfonium bases.
Among the transition metal, alkali metal and alkaline earth metal salt formers, special
mention should be made of the hydroxides of copper, iron, lithium, sodium, potassium,
magnesium and calcium, and preferably the hydroxides, bicarbonates and carbonates of
sodium and potassium . Accordingly, in one particular embodiment of the invention , G is an
agriculturally acceptable metal such as copper, iron, lithium, sodium, potassium, magnesium
or calcium (more particularly an agriculturally acceptable alkali metal or alkaline earth metal).
Examples of amines suitable for ammonium salt formation include ammonia as well as
primary, secondary and tertiary C -C 8alkylamines, Ci-C4hydroxyalkylamines and
C2-C4alkoxyalkyl-amines, for example methylamine, ethylamine, n-propylamine,
isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine,
heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine,
heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine,
methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine,
ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine,
dimethylamine, diethylamine, di-n-propylamine, di-isopropylamine, di-n-butylamine, di-namylamine,
di-isoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, npropanolamine,
isopropanolamine, L/,/V-diethanolamine, /V-ethylpropanolamine, Nbutylethanolamine,
allylamine, n-but-2-enylamine, n-pent-2-enylamine, 2,3-dimethylbut-2-
enylamine, dibut-2-enylamine, n-hex-2-enylamine, propylenediamine, trimethylamine,
triethylamine, tri-n-propylamine, tri-isopropylamine, tri-n-butylamine, tri-isobutylamine, tri-secbutylamine,
tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines,
for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline,
quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines,
ethoxyanilines, , m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and
0-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.
Accordingly, in one particular embodiment of the invention, G is an
agriculturally acceptable ammonium group, wherein the compound of formula (I) is an
ammonium salt formed from: ammonia, a primary, secondary or tertiary C -C 8alkylamine, a
Ci-C4hydroxyalkylamine, or a C2-C4alkoxyalkyl-amine.
Preferred quaternary ammonium bases suitable for salt formation correspond, for example,
to the formula [N(R aa R R R )]OH , wherein Raa, R , R and R are each independently of
the others hydrogen or Ci-C4alkyl. Further suitable tetraalkylammonium bases with other
anions can be obtained, for example, by anion exchange reactions. Accordingly, in one
particular embodiment of the invention, G is an agriculturally acceptable ammonium group,
wherein the compound of formula (I) is a salt formed from a quaternary ammonium base of
formula [N(Raa R R R )]OH, wherein Raa, R , R and R are each independently of the
others hydrogen or CrC 4alkyl.
Preferred tertiary sulfonium bases suitable for salt formation correspond, for example, to the
formula [SReeRf R"]OH, wherein Ree, Rf and R are each independently of the others C C4
alkyl. Trimethylsulfonium hydroxide is especially preferred. Suitable sulfonium bases may be
obtained from the reaction of thioethers, in particular dialkylsulfides, with alkylhalides,
followed by conversion to a suitable base, for example a hydroxide, by anion exchange
reactions. Accordingly, in one particular embodiment of the invention, G is an agriculturally
acceptable sulfonium group, wherein the compound of formula (I) is a salt formed from a
tertiary sulfonium base of formula [SReeRf R"]OH, wherein Ree, Rf and R are each
independently of the others C C4 alkyl.
It should be understood that in those compounds of formula I , where G is a metal,
ammonium group or sulfonium group as mentioned above, and as such represents a cation,
the corresponding negative charge is largely delocalised across the 0-C=C-C=0 unit within
formula (I).
The compounds of formula I according to the invention also include hydrates which may be
formed during the salt formation.
When G is -C(Xa)-Ra, -C(X )-X -R , -C(X )-N(R )-R , -S0 2-Re, -P(Xe)(R )-R9, -CH2-X -Rh; or
phenyl-CH 2- or phenyl-CH(C -C2alkyl)- (in each of which the phenyl is optionally substituted),
or heteroaryl-CH 2- or heteroaryl-CH(C -C2alkyl)- (in each of which the heteroaryl is optionally
substituted), or phenyl-C(0)-CH 2- (wherein the phenyl is optionally substituted); or
C C6alkoxy-C(0)-CH 2- , C C6alkoxy-C(0)-CH=CH-, C2-C7alken-1-yl-CH 2- , C2-C7alken-1-
yl-CH(C C2alkyl)-, C2-C4fluoroalken-1-yl-CH 2- , C2-C7alkyn-1-yl-CH 2- , or C2-C7alkyn-1-yl-
CH(Ci-C2alkyl)-; generally these G groups are latentiating groups (i.e. leaving or removeable
groups), which are generally selected to allow their removal, typically by one or a
combination of biochemical, chemical or physical processes, to afford the corresponding
compound of formula (I) where G is H, before, during or following (preferably during or
following, more preferably following) application of the compound of formula (I) to the treated
area (e.g. field) or to plants. Examples of these processes include enzymatic cleavage or
other in/on-plant cleavage (e.g. cleavage of ester and/or carbonate moieties), chemical
hydrolysis, and/or photoloysis. Some compounds bearing such groups G occasionally offer
certain advantages or different technical properties, such as improved and/or more
consistent and/or different penetration of the cuticula of the plants treated, increased and/or
different tolerance of certain crops, improved and/or different compatibility or stability in
formulated mixtures containing other herbicides, herbicide safeners, plant growth regulators,
fungicides or insecticides, or reduced and/or different leaching properties in soils.
The preferred, suitable and/or particular values of the substituents in or other features of the
compound of formula (I), in particular G, X, R , R2, R2 , R2B, R2C, R3, R4, R5, R6, R7, R8, R9,
10 11 12 13 14 15 16 17 18 19 20 2 1 22 23 a b c d e g
Xa, X , X , X , Xe, X , Q, Het, X1, n 1, n2 and/or n3, are set out below (and/or generally herein),
and can be either taken alone or taken together with one or more of any other preferred,
suitable and/or particular features in any combination(s) thereof. In this paragraph,
"preferred" is intended to encompass more preferred, even or still or yet more preferred,
particularly or highly preferred, most preferred and all similar terms.
In a particular embodiment, G is hydrogen; an agriculturally acceptable metal (e.g. an
agriculturally acceptable alkali metal or alkaline earth metal, e.g. lithium, sodium, potassium,
magnesium or calcium), or an agriculturally acceptable sulfonium or ammonium group; or G
is -C(Xa)-Ra, -C(X )-X -R or -S0 2-Re, wherein Xa, Ra, X , X , R and Re are as defined herein.
In one preferred embodiment, G is hydrogen; an agriculturally acceptable metal (e.g. an
agriculturally acceptable alkali metal or alkaline earth metal, e.g. lithium, sodium, potassium,
magnesium or calcium), or an agriculturally acceptable sulfonium or ammonium group; or G
is -C(Xa)-Ra or -C(X )-X -R , wherein Xa, Ra, X , X and R are as defined herein.
In a particular embodiment, G is a group -C(Xa)-Ra or -C(X )-X -R , wherein Xa, Ra, X , X
and R are as defined herein.
Preferably, Xa, X , X , X , Xe and/or X are oxygen. Alternatively, preferably, X is sulfur.
More preferably, Xa, X , X , X , Xe and Xf are oxygen.
Preferably, Ra is CrCi 0alkyl (e.g. CrC 6alkyl), C2-C6alkenyl (e.g. C2-C4alkenyl), C2-C6alkynyl
(e.g. C2-C4alkynyl), C3-C6cycloalkyl or Ci-C4alkoxyCi-C 4alkyl. Alternatively, preferably, Ra is
C3-C7cycloalkyl(Ci-C 5)alkyl, or phenyl or phenyl substituted by 1, 2 or 3 of, independently, -
C3alkyl, CrC 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro.
Preferably, R is C C 0alkyl (e.g. C C6alkyl), C2-C5alkenyl-CH 2- (e.g. C2-C3alkenyl-CH 2-),
C2-C4alkenyl-CH(Me)- (e.g. C2-C3alkenyl-CH(Me)-), C2-C5alkynyl-CH 2- (e.g.
C2-C3alkynyl-CH2-), C2-C4alkynyl-CH(Me)- (e.g. C2-C3alkynyl-CH(Me)-), C3-C6cycloalkyl or
Ci-C 4alkoxyCi-C 4alkyl. Alternatively, preferably, R is C3-C7cycloalkyl(Ci-C 5)alkyl, or phenyl
or phenyl substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro.
Preferably, Re is CrC 10alkyl (e.g. CrC 6alkyl or C1-C4alkyl) or CrC 10fluoroalkyl (e.g. C
C3fluoroalkyl). In particular, Re is CrC 10alkyl (e.g. CrCealkyl or C1-C4alkyl).
When G is -C(Xa)-Ra or -C(X )-X -R , then preferably Xa, X and X are oxygen, Ra is C
C 0alkyl (e.g. CrC 6alkyl), C2-C6alkenyl (e.g. C2-C4alkenyl), C2-C6alkynyl (e.g. C2-C4alkynyl),
C3-C6cycloalkyl or C1-C4alkoxyC 1-C4alkyl; and R is CrC 10alkyl (e.g. CrCealkyl),
C2-C5alkenyl-CH 2- (e.g. C2-C3alkenyl-CH 2-), C2-C4alkenyl-CH(Me)- (e.g.
C2-C3alkenyl-CH(Me)-), C2-C5alkynyl-CH 2- (e.g. C2-C3alkynyl-CH2-),
C2-C4alkynyl-CH(Me)- (e.g. C2-C3alkynyl-CH(Me)-), C3-C6cycloalkyl or Ci-C 4alkoxyCi-C 4alkyl.
In a preferable embodiment, G is hydrogen, or an agriculturally acceptable alkali metal or
alkaline earth metal, or an agriculturally acceptable sulfonium or ammonium group. More
preferably, G is hydrogen, or an agriculturally acceptable alkali metal or alkaline earth metal.
In a preferable embodiment, G is hydrogen, -C(Xa)-Ra or -C(X )-X -R .
Most preferably G is hydrogen.
In one particular embodiment of the invention, X is chlorine.
However, in the present invention, most preferably, X is methyl.
In one preferable embodiment of the invention, R is chlorine.
However, in the present invention, most preferably, R is methyl.
Therefore, e.g. in all aspects and/or embodiments of the invention, most preferably, X is
methyl, and R is methyl.
In an alternative, also highly preferable, embodiment of the invention (which e.g. can apply to
all aspects and/or embodiments of the invention), X is methyl, and R is chlorine.
In another alternative preferable embodiment of the invention (which e.g. can apply to all
aspects and/or embodiments of the invention), X is chlorine, and R is methyl.
In an alternative particular embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), X is chlorine, and R is chlorine.
In the invention, R2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine,
chlorine, bromine, CrCsalkoxy (e.g. methoxy, ethoxy, n-propoxy or isopropoxy),
C -C2fluoroalkoxy (e.g. Cifluoroalkoxy such as difluoromethoxy or trifluoromethoxy; or e.g.
CF3CH2O-), C1-C2alkoxy-C 1-C3alkoxy-, or dfluoroalkoxy-CrCsalkoxy-.
Preferably, when R2 is C -C2alkoxy-C -C3alkoxy- or C-ifluoroalkoxy-C-i-Csalkoxy-, then R2 is
R2 0-CH(R 2B)-CH(R2C)-0-;
wherein R2 is CrC 2alkyl (in particular methyl) or dfluoroalkyl; and
R2B and R2C are independently hydrogen or methyl, provided that one or both of R2B and R2C
are hydrogen.
Preferably, R2 is methyl or Cifluoroalkyl, more preferably methyl.
Preferably, both of R and R are hydrogen.
More preferably, when R2 is Ci-C 2alkoxy-Ci-C 3alkoxy- or Cifluoroalkoxy-Ci-C 3alkoxy- (in
particular when R2 is R2 0-CH(R 2B)-CH(R2C)-0-), then R2 is MeO-CH2-CH2-0-.
Preferably, e.g. in all aspects and/or embodiments of the invention, R2 is hydrogen, methyl,
ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy or
fluoromethoxy (i.e. Cifluoroalkoxy). Alternatively, preferably, R2 is MeO-CH2-CH2-0-.
Preferably, e.g. in all aspects and/or embodiments of the invention, R2 is methyl, ethyl, npropyl,
cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy or
fluoromethoxy (i.e. Cifluoroalkoxy). Alternatively, preferably, R2 is MeO-CH2-CH2-0-.
Alternatively or additionally, preferably, e.g. in all aspects and/or embodiments of the
invention, R2 is hydrogen, methyl, ethyl, ethynyl, chlorine, methoxy or fluoromethoxy (i.e.
Cifluoroalkoxy, e.g. monofluoromethoxy, difluoromethoxy or trifluoromethoxy). Alternatively,
preferably, R2 is ethoxy or MeO-CH2-CH2-0-.
More preferably, e.g. in all aspects and/or embodiments of the invention, R2 is not hydrogen.
More preferably, e.g. in all aspects and/or embodiments of the invention, R2 is methyl, ethyl,
ethynyl, chlorine, methoxy or fluoromethoxy (i.e. Cifluoroalkoxy, e.g. monofluoromethoxy,
difluoromethoxy or trifluoromethoxy). Alternatively, more preferably, R2 is ethoxy or
MeO-CH2-CH2-0-, preferably ethoxy.
Even more preferably, e.g. in all aspects and/or embodiments of the invention, R2 is methyl,
ethynyl, chlorine or methoxy. Alternatively, even more preferably, R2 is ethoxy.
Still more preferably, e.g. in all aspects and/or embodiments of the invention, R2 is methyl,
chlorine or methoxy. Alternatively, still more preferably, R2 is ethoxy.
Yet more preferably, e.g. in all aspects and/or embodiments of the invention, R2 is methyl or
methoxy.
Most preferably, e.g. in all aspects and/or embodiments of the invention, R2 is methyl.
Therefore, more preferably, e.g. in all aspects and/or embodiments of the invention:
R is methyl, and
R2 is methyl, ethyl, ethynyl, chlorine, methoxy orfluoromethoxy; still more preferably methyl,
chlorine or methoxy; yet more preferably methyl or methoxy; most preferably methyl.
In an alternative more preferable embodiment, e.g. in all aspects and/or embodiments of the
invention:
R is chlorine, and
R2 is ethyl, ethynyl, chlorine, methoxy orfluoromethoxy; still more preferably chlorine or
methoxy; most preferably methoxy.
In a further alternative more preferable embodiment, e.g. in all aspects and/or embodiments
of the invention:
R is chlorine, and
R2 is ethoxy or MeO-CH2-CH2-0-, still more preferably ethoxy.
In a most preferable embodiment of the invention (which e.g. can apply to all aspects and/or
embodiments of the invention), R is methyl, R2 is methyl, and X is methyl or chlorine (most
preferably methyl).
In an alternative highly preferable embodiment of the invention (which e.g. can apply to all
aspects and/or embodiments of the invention), R is methyl, R2 is chlorine, and X is methyl or
chlorine (preferably methyl).
In an alternative preferable embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), R is methyl, R2 is ethynyl, and X is methyl or chlorine
(preferably methyl).
In an alternative preferable embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), R is methyl, R2 is methoxy, and X is methyl or
chlorine (preferably methyl).
In an alternative particular embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), R is methyl, R2 is hydrogen, and X is methyl or
chlorine (preferably methyl).
In an alternative very highly preferable embodiment of the invention (which e.g. can apply to
all aspects and/or embodiments of the invention), R is chlorine, R2 is methoxy, and X is
methyl or chlorine (preferably methyl).
In an alternative highly preferable embodiment of the invention (which e.g. can apply to all
aspects and/or embodiments of the invention), R is chlorine, R2 is chlorine, and X is methyl
or chlorine (preferably methyl).
In an alternative particular embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), R is chlorine, R2 is hydrogen, and X is methyl or
chlorine (preferably methyl).
In an alternative highly preferable embodiment of the invention (which e.g. can apply to all
aspects and/or embodiments of the invention), R is chlorine, R2 is ethoxy, and X is methyl or
chlorine (preferably methyl).
Preferably, e.g. in all aspects and/or embodiments of the invention, when R4 and R5 are
taken together, then R4 and R5 taken together are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- .
Preferably, R7a is C C2alkyl; and R7 is hydrogen or C C2alkyl.
Preferably, n4 is 2 or 3.
Preferably, n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 1 or 2.
Preferably, e.g. in all aspects and/or embodiments of the invention, when R4 and R5 are
taken together (which is preferable), then R4 and R5 taken together
are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- ;
wherein R7a is CrC 2alkyl; R7 is hydrogen or Ci-C2alkyl;
n4 is 1, 2 or 3 (preferably 2 or 3); and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 0, 1 or 2 (preferably 1 or 2).
Preferably, e.g. in all aspects and/or embodiments of the invention, R3, R4, R5 and/or R6,
independently of each other, are hydrogen, Ci-C4alkyl (e.g. Ci-C2alkyl), C2-C4alkynyl (in
particular C2-C3alkynyl-CH2- , e.g. ethynyl-CH2-), d-dalkoxyd-dalkyl, d-dalkylthiod-
C3alkyl, d-dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl; d-dcycloalkyl (in
particular cyclopropyl); or an unsubstituted 4, 5 or 6 (e.g. 4 or 5) membered monocyclic
heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and
nitrogen, and attached at a ring carbon atom within the heterocyclyl (in particular
tetrahydrofuranyl such as tetrahydrofuran-3-yl, or tetrahydropyranyl such as tetrahydropyran-
4-yl);
provided that no more than one (in particular none) of R3, R4, R5 and R6 is alkenyl, alkynyl,
alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
or R3 and R4 taken together are -(CH2) 1- or -(CH2) 2-X -(CH2) 3- and R5 and R6 are as
defined herein (e.g. hereinabove), or R5 and R6 taken together
are -(CH2) - or -(CH2) 2-X -(CH2) 3- and R3 and R4 are as defined herein (e.g. hereinabove);
wherein X1 is O, S, S(O), S(0) 2, NH, N(d-C 2alkyl), N(d-C 2alkoxy), C(H)(C dalkyl),
C(d-dalkyl) 2 or C(H)(d-C 2alkoxy);
n 1 is 4 or 5; and
n2 and n3 are independently 1, 2 or 3 provided that n2 + n3 is 3 or 4;
and/or R4 and R5 taken together are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- ;
wherein R7a is d-dalkyl; R7 is hydrogen or d-C 2alkyl;
n4 is 1, 2 or 3 (in particular 2 or 3); and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 0, 1 or 2 (in particular 1 or 2).
More preferably, e.g. in all aspects and/or embodiments of the invention, R3, R4, R5 and/or
R6, independently of each other, are hydrogen, CrC 4alkyl (e.g. CrC 2alkyl), C2-C4alkynyl (in
particular C2-C3alkynyl-CH2- , e.g. ethynyl-CH2-), C -C3alkoxyCi-C 3alkyl (in particular
C -C2alkoxyCi-C 2alkyl), C -C3alkylthioCi-C 3alkyl (in particular C -C2alkylthioCi-C 2alkyl),
C -C3alkylsulfinylCrC 3alkyl (in particular C -C2alkylsulfinylCi-C 2alkyl),
C -C3alkylsulfonylCrC 3alkyl (in particular C -C2alkylsulfonylCi-C 2alkyl); C3-C4cycloalkyl (in
particular cyclopropyl); or an unsubstituted 4, 5 or 6 (e.g. 4 or 5) membered monocyclic
heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and
nitrogen, and attached at a ring carbon atom within the heterocyclyl (in particular
tetrahydrofuranyl such as tetrahydrofuran-3-yl, or tetrahydropyranyl such as tetrahydropyran-
4-yl);
provided that no more than one (in particular none) of R3, R4, R5 and R6 is alkenyl, alkynyl,
alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
and/or R4 and R5 taken together are -(CH2)n4- or -(CH2) n5-C(R7a)(R7 )-(CH2 )n6-;
wherein R7a is C -C2alkyl; R7 is hydrogen or C -C2alkyl;
n4 is 2 or 3; and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 1 or 2.
Still more preferably, R3, R4, R5 and/or R6, independently of each other, are hydrogen,
C -C3alkyl (in particular C -C2alkyl such as methyl) or C -C3alkoxyC -C3alkyl (in particular
C -C2alkoxyC -C2alkyl); provided that no more than one (in particular none) of R3, R4, R5 and
R6 is alkoxyalkyl;
and/or R4 and R5 taken together are -(CH2)n4- or -(CH2) n5-C(R7a)(R7 )-(CH2 )n6-;
wherein R7a is C -C2alkyl; R7 is hydrogen or C -C2alkyl;
n4 is 2 or 3; and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 1 or 2.
Even more preferably, R3, R4, R5 and/or R6, independently of each other, are hydrogen or -
C2alkyl (preferably hydrogen or methyl); and/or R4 and R5 taken together
are -(CH2)n4- wherein n4 is 2 or 3.
Most preferably (especially when Y is CR R9 or -CR 0R CR 2R13-), R3, R4, R5 and R6 are
hydrogen; or R4 and R5 taken together are -(CH2 ) n4- wherein n4 is 2 or 3, and R3 and R6 are
hydrogen.
Preferably, e.g. in all aspects and/or embodiments of the invention, at least one (more
preferably 2, 3 or 4, still more preferably 3 or 4, most preferably all four) of R3, R4, R5 and R6,
independently of each other, are hydrogen or C -C4alkyl (e.g. H or C -C3alkyl, or H or
C C2alkyl);
or R4 and R5 are taken together as described herein.
Preferably, e.g. in all aspects and/or embodiments of the invention, Y is O, S, S(O), S(0) 2,
C(O), CR R or -CR 0R CR 2R13- .
More preferably, Y is O, C(O), CR R or -CR 0R CR 2R13- .
Even more preferably, Y is O or CR R , in particular O or CH2.
Most preferably, Y is CR R9, in particular CH2.
Preferably, e.g. in all aspects and/or embodiments of the invention, in R8 and R9, one or both
of R8 and R9 is or are hydrogen; or R8 and R9 taken together are -(CH2) 7- or preferably
-(CH2) 8-X2-(CH2) 9- . In this embodiment, preferably Y is CR R9 and/or preferably X2 is O.
In one particular embodiment, R8 and R9 are taken together and are -(CH2) 7- or preferably
-(CH2) 8-X2-(CH2) 9- . In this embodiment, preferably Y is CR R9 and/or preferably X2 is O.
Preferably, e.g. in all aspects and/or embodiments of the invention, X2 is O, S, S(O), S(0) 2,
C(H)(C C3alkyl), C(C C2alkyl)2 or C(H)(C C3alkoxy). Most preferably, X2 is O.
Preferably, n7 is 2, 3, 4 or 5, more preferably 4 or 5.
Preferably, n8 and n9 are independently 1, 2 or 3 provided that n8 + n9 is 2, 3 or 4.
Preferably, n8 + n9 is 3 or 4. Most preferably, n8 is 2 and n9 is 2 (in which case, preferably,
X2 is O).
Preferably, e.g. in all aspects and/or embodiments of the invention, R8 and R are,
independently of each other:
hydrogen, -C4alkyl (in particular CrC 2alkyl), C2-C3alkenyl-CH 2- (in particular
ethenyl-CH 2-), C2-C3alkynyl-CH 2- (in particular ethynyl-CH 2-), CrC 2fluoroalkyl (in particular
Cifluoroalkyl), Ci-C 3alkoxyCi-C 3alkyl, Ci-C 3alkylthioC C3alkyl, Ci-C 3alkylsulfinylC C3alkyl,
or Ci-C 3alkylsulfonylC C3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are CrC 3alkyl (in particular methyl or ethyl) or Ci-C 2fluoroalkyl; and in which
one ring CH2 moiety of a C4-C6cycloalkyl is optionally (e.g. preferably) replaced by an oxygen
or sulfur atom or by a S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being C-i-C3alkoxy (in particular
C-i-C2alkoxy) and optionally further substituted by one substituent being C -C2alkyl (in
particular methyl);
C3-C6cycloalkylCrC 2alkyl- (in particular C3-C6cycloalkylmethyl-) or C3-C6cycloalkylCr
C2alkyl- (in particular C3-C6cycloalkylmethyl-) substituted by one or two ring substituents
which independently are CrC 3alkyl or Ci-C 2fluoroalkyl; and in which one ring CH2 moiety of a
C4-C6cycloalkylCi-C 2alkyl- (in particular C4-C6cycloalkylmethyl-) is optionally (e.g. preferably)
replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C1-C2alkyl), N(C
C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety;
Cs-CecycloalkylCrC^alkyl- (in particular C3-C6cycloalkylmethyl-) substituted by one ring
substituent being C-i-C3alkoxy (in particular C-i-C2alkoxy) and optionally further substituted by
one ring substituent being C -C2alkyl (in particular methyl); or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon, which is
optionally substituted by 1, 2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents
independently being C C3alkyl (e.g. C C2alkyl), C C2fluoroalkyl, C C3alkyl-C(0)-,
CrC 2fluoroalkyl-C(0)-, hydroxy (including any oxo tautomer), C2-C3alkenyl (e.g. ethenyl or
prop-1-enyl), C2-C3alkynyl (e.g. ethynyl or prop-1-ynyl), Ci-C 3alkoxy (e.g. Ci-C 2alkoxy), C
C2fluoroalkoxy, halogen (e.g. fluorine or chlorine), cyano or nitro, provided that any nonfluorine
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 -C3alkyl, C -C2fluoroalkyl , C -C3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or
C -C2alkyl-S(0) 2- substituent;
provided that no more than one of R8 and R is an optionally substituted cycloalkyl; an
optionally substituted cycloalkyl in which one ring CH2 moiety has been replaced by an
oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl),
N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety; an optionally
substituted cycloalkenyl ; an optionally substituted cycloalkyl-alkyl-; an optionally substituted
cycloalkyl-alkyl- in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom
or by a S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety; or Het or Het-CH 2- ;
or R8 is hydrogen or C -C2alkyl (in particular H or Me), and R is C -C2alkoxy (in particular
methoxy);
or R8 and R9 taken together are -(CH 2) 7- or -(CH2) 8-X2-(CH 2) 9- .
In the above preferred embodiment, preferably Y is CR R9 and/or preferably X2 is O.
More preferably, e.g. in all aspects and/or embodiments of the invention:
R8 is hydrogen or C -C2alkyl (preferably H or Me, more preferably hydrogen); and
R9 is:
CrC 2alkoxy (in particular methoxy);
C2-C3alkynyl-CH 2- (in particular ethynyl-CH 2-);
C -C3alkoxyCrC 3alkyl;
C -C3alkylthioCrC 3alkyl (preferably CrC 2alkylthio-CH 2CH2- or more preferably
CrC 2alkylthio-CH(Me)CH 2-);
C -C3alkylsulfinylC C3alkyl;
C -C3alkylsulfonylC C3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are C -C3alkyl (in particular methyl or ethyl) or C -C2fluoroalkyl; and in which
one ring CH2 moiety of a C4-C6cycloalkyl is optionally (e.g. preferably) replaced by an oxygen
or sulfur atom or by a S(O), S(0) 2, NH, N(CrC 3alkyl), N(CrC 2fluoroalkyl), N[C(0)CrC 3alkyl],
N[C(0)CrC 2fluoroalkyl] or N(CrC 2alkoxy) moiety (or more preferably is replaced by an
oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C C3alkyl) or N(C C2alkoxy) moiety; or
still more preferably is replaced by an oxygen or sulfur atom);
C3-C6cycloalkyl substituted by one substituent being -C3alkoxy (in particular
CrC 2alkoxy) and optionally further substituted by one substituent being Ci-C 2alkyl (in
particular methyl);
C3-C6cycloalkylmethyl- or C3-C6cycloalkylmethyl- substituted by one or two ring
substituents which independently are CrC 3alkyl (in particular Ci-C 2alkyl) or Ci-C 2fluoroalkyl;
and in which one ring CH2 moiety of a C4-C6cycloalkylmethyl- is optionally (e.g. preferably)
replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C C2alkyl), N(C
C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety (or more
preferably is replaced by an oxygen or sulfur atom or by a N[C(0)CrC 3alkyl] or
N[C(0)C C2fluoroalkyl] moiety);
C3-C6cycloalkylmethyl- substituted by one ring substituent being C-i-C3alkoxy (in
particular C-i-C2alkoxy) and optionally further substituted by one ring substituent being
C -C2alkyl (in particular methyl); or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon, which is
optionally substituted by 1, 2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents
independently being C -C3alkyl (in particular C -C2alkyl), C -C2fluoroalkyl (in particular
dfluoroalkyl), d-Csalkyl-C^O)-, d-dfluoroalkyl-C(O)-, hydroxy (including any oxo
tautomer), C2-C3alkenyl (in particular ethenyl or prop-1-enyl), C2-C3alkynyl (in particular
ethynyl or prop-1-ynyl), -C3alkoxy (in particular d-dalkoxy), d-dfluoroalkoxy (in
particular Cifluoroalkoxy), halogen (in particular fluorine or chlorine), 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 C3alkyl, C C2fluoroalkyl, C C3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or
Ci-C 2alkyl-S(0) 2- substituent;
or R8 and R9 taken together are -(CH2) 7- or -(CH2) 8-X2-(CH2) 9- .
In the above more preferred embodiment, preferably Y is CR R and/or preferably X2 is O.
Even more preferably, e.g. in all aspects and/or embodiments of the invention:
R8 is hydrogen or CrC 2alkyl (preferably H or Me, more preferably hydrogen); and
R9 is:
Ci-C 3alkylthioCi-C 3alkyl (preferably Ci-C 2alkylthio-CH 2CH2- or more preferably
CrC 2alkylthio-CH(Me)CH 2-);
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are CrC 3alkyl (in particular methyl or ethyl) or Ci-C 2fluoroalkyl; and in which
one ring CH2 moiety of a C4-C6cycloalkyl is replaced by an oxygen or sulfur atom or by a
S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)C 1-C2fluoroalkyl] or N( -C2alkoxy) moiety (or preferably is replaced by an oxygen or
sulfur atom or by a S(O), S(0) 2, NH, N(C C3alkyl) or N(C C2alkoxy) moiety; or more
preferably is replaced by an oxygen or sulfur atom);
C3-C6cycloalkylmethyl- or C3-C6cycloalkylmethyl- substituted by one or two ring
substituents which independently are C -C3alkyl (in particular C -C2alkyl) or C-i-C2fluoroalkyl;
and in which one ring CH2 moiety of a C4-C6cycloalkylmethyl- is replaced by an oxygen or
sulfur atom or by a S(O), S(0) 2, NH, N(C C2alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)Ci-C 2fluoroalkyl] or N(Ci-C 2alkoxy) moiety (or preferably is replaced by an oxygen or
sulfur atom or by a N[C(0)C C3alkyl] or N[C(0)C C2fluoroalkyl] moiety); or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon, which is
optionally substituted by 1, 2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents
independently being C -C3alkyl (in particular C -C2alkyl), C-i-C2fluoroalkyl (in particular
dfluoroalkyl), d-dalkyl-C(O)-, d-dfluoroalkyl-C(O)-, hydroxy (including any oxo
tautomer), C2-C3alkenyl (in particular ethenyl or prop-1-enyl), C2-C3alkynyl (in particular
ethynyl or prop-1-ynyl), -C3alkoxy (in particular d-dalkoxy), d-C 2fluoroalkoxy (in
particular Cifluoroalkoxy), halogen (in particular fluorine or chlorine), 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 d-dalkyl, d-dfluoroalkyl, d-dalkyl-C(O)-, d-C 2fluoroalkyl-C(0)- or
d-C 2alkyl-S(0) 2- substituent;
or R8 and R9 taken together are -(CH2) 7- or -(CH2) 8-X2-(CH2) 9- .
In the above even more preferred embodiment, preferably Y is CR R and/or preferably X2 is
O.
In one preferable embodiment (which e.g. can apply to all aspects and/or embodiments of
the invention), R8 and R are, independently of each other, hydrogen or CrC 3alkyl
(preferably hydrogen or CrC 2alkyl, such as hydrogen or methyl). In this embodiment,
preferably, Y is CR R9.
In another preferable embodiment (which e.g. can apply to all aspects and/or embodiments
of the invention), R8 is hydrogen , and R9 is d-CsalkylthioCrCsalkyl. In this embodiment, R9
preferably is C -C2alkylthio-CH 2CH2- or more preferably is C -C2alkylthio-CH (Me)CH2- . In
this embodiment, preferably, Y is CR R9.
In another preferable embodiment (which e.g. can apply to all aspects and/or embodiments
of the invention), R8 is hydrogen and R9 is C4-C6cycloalkylmethyl- or
C4-C6cycloalkylmethyl- substituted by one or two ring substituents which independently are
CrC 3alkyl (in particular C -C2alkyl) or CrC 2fluoroalkyl, and in which one ring CH2 moiety is
replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C C2alkyl), N(C
C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety (or more
preferably is replaced by an oxygen or sulfur atom or by a N[C(0)C 1-C3alkyl] or
N[C(0)C C2fluoroalkyl] moiety). In this embodiment, preferably, Y is CR R9.
In this preferable embodiment, then more preferably R8 is hydrogen and R9 is a
heterocyclyl-methyl-, wherein the heterocyclyl is Q, wherein Q is one of the following subformulae
Q i , Q 2 , Q 3 , Q 4 , Q 5 , <¾, Q 7 , Q33, ¾ 4 , Q37, <¾8, Q 4 i , Q42, Q43, Q 44 , Q 47 , ¾ , <¾9, Q90 or
Q107 '
wherein:
A is the position of attachment to the -methyl- moiety; and
R is hydrogen, C1-C2alkyl (e.g. methyl), C1-C2fluoroalkyl (e.g.
Cifluoroalkyl), -C(0)C C3alkyl (e.g. -C(O)methyl), -C(0)C C2fluoroalkyl
(e.g. -C(O)Cifluoroalkyl) or CrC 2alkoxy.
More preferably, Q is one of the sub-formulae Q , Q 2 , Q4 , <¾, Q7, Q33, Q 34 , Q4 i , Q 42, Q43, Q44 ,
Q87, Qs9 or Q90. Even more preferably, Q is one of the sub-formulae Q2, Q6, Q7, Q33, Q 34 , Q4 i
Q42 , Q 43, Q44 , Q 87 9 or Q g0 .
Yet more preferably, Q is one of the sub-formulae Q2, Q7, Q87 or Q90. Further more
preferably, Q is one of the sub-formulae Q2, Q7 or Q90.
Most preferably, Q is sub-formula Q7.
Preferably, R is -C(0)C C3alkyl (e.g. -C(O)methyl) or -C(0)C C2fluoroalkyl
(e.g. -C(O)Cifluoroalkyl).
In one preferable embodiment of the invention (which e.g. can apply to all aspects and/or
embodiments of the invention), R8 is hydrogen, and R is tetrahydro-2/-/-pyran-4-yl (
) or (tetrahydro-2H-pyran-4-yl)-methyl-. In this embodiment, preferably, Y is
CR R . When R is (tetrahydro-2/-/-pyran-4-yl)-methyl-, then R is Q7-methyl- wherein Q7 is
wherein A is the position of attachment to the -methyl- moiety.
In another preferable embodiment (which e.g. can apply to all aspects and/or embodiments
of the invention), R8 is hydrogen and R9 is Het or Het-CH2- as defined herein. In this
embodiment, more preferably, R8 is hydrogen and R9 is Het as defined herein. In this
embodiment, preferably, Y is CR R9.
Preferably, e.g. in all aspects and/or embodiments of the invention, Het is a heteroaryl (in
particular monocyclic heteroaryl), attached at a ring-carbon, which is optionally substituted by
1, 2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents independently being C -C2alkyl,
Cifluoroalkyl, C1-C2alkyl-C(0)-, Cifluoroalkyl-CiO)-, hydroxy (including any oxo tautomer),
ethynyl, prop-1-ynyl, C -C2alkoxy, C-ifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro,
provided that any chlorine, bromine, 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 ringnitrogen
atom not partaking in a C=N ring double bond by one CrC 3alkyl, CrC 2fluoroalkyl,
C C3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent.
More preferably, e.g. in all aspects and/or embodiments of the invention, Het is a heteroaryl
(in particular monocyclic heteroaryl), attached at a ring-carbon, which is optionally substituted
by 1 or 2 (in particular 1) ring-carbon substituents independently being Ci-C 2alkyl (in
particular methyl), Cifluoroalkyl (in particular CF3) , Ci-C 2alkyl-C(0)- (in particular Me-C(O)-),
Cifluoroalkyl-C(O)-, ethynyl, prop-1-ynyl, fluorine or cyano;
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 ringnitrogen
atom not partaking in a C=N ring double bond by one C -C2alkyl (e.g. methyl),
Cifluoroalkyl, methyl-C(O)- or Cifluoroalkyl-C(O)- substituent.
More preferably, e.g. in all aspects and/or embodiments of the invention, Het is a heteroaryl
(in particular monocyclic heteroaryl), attached at a ring-carbon, which is optionally substituted
by 1 or 2 (in particular 1) ring-carbon substituents independently being C -C2alkyl (in
particular methyl), Cifluoroalkyl (in particular CF3) , fluorine or cyano;
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 ringnitrogen
atom not partaking in a C=N ring double bond by one methyl substituent.
Preferably, e.g. in all aspects and/or embodiments of the invention, Het is an optionally
substituted monocyclic heteroaryl, attached at a ring-carbon. Such as monocyclic heteroaryl
can be 5-membered or 6-membered monocyclic heteroaryl.
More preferably, e.g. in all aspects and/or embodiments of the invention, Het is an optionally
substituted monocyclic heteroaryl, attached at a ring-carbon, which is:
pyridinyl (preferably pyridin-3-yl or most preferably pyridin-2-yl), pyrazolyl (preferably pyrazol-
5-yl or pyrazol-4-yl, or most preferably pyrazol-3-yl), imidazolyl (preferably imidazol-2-yl),
pyrazinyl, pyrimidinyl (preferably pyrimidin-4-yl), pyridazinyl (preferably pyridazin-3-yl),
triazolyl (e.g. 1,2,3-triazolyl), tetrazol-5-yl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl or
oxadiazolyl; optionally present (e.g. where chemically possible) as an agrochemically
acceptable salt thereof (such as an agrochemically acceptable acid addition salt thereof).
Even more preferably, e.g. in all aspects and/or embodiments of the invention, Het is an
optionally substituted monocyclic heteroaryl, attached at a ring-carbon, which is:
pyridinyl (preferably pyridin-3-yl or most preferably pyridin-2-yl), pyrazolyl (preferably pyrazol-
5-yl or pyrazol-4-yl, or most preferably pyrazol-3-yl), imidazolyl (preferably imidazol-2-yl),
pyrazinyl, pyrimidinyl (preferably pyrimidin-4-yl), pyridazinyl (preferably pyridazin-3-yl),
triazolyl (e.g. 1,2,3-triazolyl), or tetrazol-5-yl; optionally present (e.g. where chemically
possible) as an agrochemically acceptable salt thereof (such as an agrochemically
acceptable acid addition salt thereof).
Still more preferably, e.g. in all aspects and/or embodiments of the invention, Het is an
optionally substituted monocyclic heteroaryl, attached at a ring-carbon, which is:
pyridinyl (preferably pyridin-3-yl or most preferably pyridin-2-yl), pyrazolyl (preferably pyrazol-
5-yl or pyrazol-4-yl, or most preferably pyrazol-3-yl), imidazolyl (preferably imidazol-2-yl),
pyrazinyl, pyrimidinyl (preferably pyrimidin-4-yl), or pyridazinyl (preferably pyridazin-3-yl);
optionally present (e.g. where chemically possible) as an agrochemically acceptable salt
thereof (such as an agrochemically acceptable acid addition salt thereof).
Yet more preferably, e.g. in all aspects and/or embodiments of the invention, Het is an
optionally substituted monocyclic heteroaryl, attached at a ring-carbon, which is:
pyridin-3-yl, pyridin-2-yl, or pyrazolyl (preferably pyrazol-5-yl or pyrazol-4-yl, or most
preferably pyrazol-3-yl); optionally present (e.g. where chemically possible) as an
agrochemically acceptable salt thereof (such as an agrochemically acceptable acid addition
salt thereof).
Most preferably, e.g. in all aspects and/or embodiments of the invention, Het is an optionally
substituted monocyclic heteroaryl, attached at a ring-carbon, which is: pyridin-2-yl or pyrazol-
3-yl; optionally present (e.g. where chemically possible) as an agrochemically acceptable salt
thereof (such as an agrochemically acceptable acid addition salt thereof).
It is particularly preferred (e.g. in all aspects and/or embodiments of the invention) that, in
Het, any ring-carbon atom, which is directly bonded to the ring-carbon atom which is the
point of attachment (e.g. or i.e. which is the point of attachment to the central carbon atom
within the Y = CR R moiety (for Het), or which is the point of attachment to the -CH2- moiety
(for Het-CH2-), is unsubstituted. Therefore, for example, preferably, when Het is an
optionally substituted pyridin-2-yl (optionally present as an agrochemically acceptable salt
thereof), then the ring-carbon atom at the 3-position of the ring (calculated with respect to the
pyridine ring nitrogen atom) is unsubstituted.
Preferably, e.g. in all aspects and/or embodiments of the invention, R 0 , R , R 2 and/or R 3
are, independently of each other, hydrogen or CrC 2alkyl (in particular hydrogen or methyl).
Preferably, two, three or all of R 0 , R , R 2 and R 3 are hydrogen.
Most preferably, R 0 , R , R 2 and R 3 are hydrogen.
In a particularly preferable embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention):
Y is O or CR R9 (preferably CR R9) ; and
R4 and R5 are taken together and are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- ;
wherein R7a is C C2alkyl; R7 is hydrogen or C C2alkyl;
n4 is 2 or 3; and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 1 or 2.
In this particularly preferable embodiment, more preferably, Y is O or CR R (preferably
CR R ) wherein R8 and R9 are, independently of each other, hydrogen or C -C3alkyl (in
particular, this C -C3alkyl can be C -C2alkyl such as methyl).
In this particularly preferable embodiment, even more preferably Y is O or CH2 ; or, most
preferably, Y is CH2.
In this particularly preferable embodiment, more preferably, R3 and R6, independently of each
other, are hydrogen, C -C3alkyl (in particular C -C2alkyl such as methyl) or
C -CaalkoxyC -Caalkyl (in particular C -C2alkoxyC -C2alkyl); provided that no more than one
(in particular none) of R3 and R6 is alkoxyalkyl.
In this particularly preferable embodiment, even more preferably, R3 and R6, independently of
each other, are hydrogen or C -C2alkyl (preferably hydrogen or methyl); and R4 and R5 taken
together are -(CH2) 4- wherein n4 is 2 or 3.
In a particularly preferable embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), the compound of formula (I) is a compound described
in any of Tables 1 to 25, as described and/or illustrated herein, optionally present (e.g. where
chemically possible) as an agrochemically acceptable salt thereof. In an alternative
particularly preferable embodiment of the invention (which e.g. can apply to all aspects
and/or embodiments of the invention), the compound of formula (I) is a compound described
Table 26 or 27, as described and/or illustrated herein, optionally present (e.g. where
chemically possible) as an agrochemically acceptable salt thereof. More preferably (e.g. in
all aspects and/or embodiments of the invention), the compound of formula (I) is a compound
described in any of Tables 1, 3, 5, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 20, 2 1, 22, 23, 24
or 25 (or alternatively in Table 26 or 27), as described and/or illustrated herein, optionally
present (e.g. where chemically possible) as an agrochemically acceptable salt thereof. Even
more preferably (e.g. in all aspects and/or embodiments of the invention), the compound of
formula (I) is a compound described in any of Tables 1, 3, 5, 8, 9, 10, 11, 12, 14, 15, 16 or 25
(or alternatively in Table 26 or 27), as described and/or illustrated herein, optionally present
(e.g. where chemically possible) as an agrochemically acceptable salt thereof.
In one more particularly preferable embodiment of the invention (which e.g. can apply to all
aspects and/or embodiments of the invention), the compound of formula (I) is compound A-1 ,
A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-1 1, A-1 2, A-1 3, A-1 4 or A-1 5, as described
and/or illustrated herein, optionally present (e.g. where chemically possible) as an
agrochemically acceptable salt thereof. In an alternative more particularly preferable
embodiment of the invention (which e.g. can apply to all aspects and/or embodiments of the
invention), the compound of formula (I) is compound A-16, A-17 or A-18, as described and/or
illustrated herein, optionally present (e.g. where chemically possible) as an agrochemically
acceptable salt thereof. In a further alternative more particularly preferable embodiment of
the invention (which e.g. can apply to all aspects and/or embodiments of the invention), the
compound of formula (I) is compound A-20 (= compound 11.10), A-22 (= compound 1.10),
A-25 (= compound 14.23), A-27 (= compound 12.02), A-28 (= compound 12.10), A-30 (=
compound 12.15), A-31 (= compound 9.02), A-32 (= compound 9.10), A-33 (= compound
1.02), A-34 (= compound 1.15), A-35 (= compound 5.02), A-36 (= compound 5.10), A-37 (=
compound 5.15), A-38 (= compound 11.02), A-39 (= compound 11.15), A-40 (= compound
25.10) or A-41 (= compound 14.06), as described and/or illustrated herein, optionally present
(e.g. where chemically possible) as an agrochemically acceptable salt thereof. In a further
alternative more particularly preferable embodiment of the invention (which e.g. can apply to
all aspects and/or embodiments of the invention), the compound of formula (I) is compound
A-1 9, A-21 , A-23, A-24, A-26, A-29, P-3, P-4, P-5 or P-7, as described and/or illustrated
herein, optionally present (e.g. where chemically possible) as an agrochemically acceptable
salt thereof.
In a yet more particularly preferable embodiment of the invention (which e.g. can apply to all
aspects and/or embodiments of the invention), the compound of formula (I) is compound A-2,
A-3, A-4, A-5, A-8, A-9, A-10, A-12, A-13, A-14, A-15, A-16, A-17 or A-18, as described
and/or illustrated herein, optionally present (e.g. where chemically possible) as an
agrochemically acceptable salt thereof; or alternatively is compound A-6, as described and/or
illustrated herein, optionally present as an agrochemically acceptable salt thereof. In an
alternative yet more particularly preferable embodiment of the invention (which e.g. can apply
to all aspects and/or embodiments of the invention), the compound of formula (I) is
compound A-20, A-22, A-27, A-28, A-33, A-34, A-35, A-36, A-38, A-39, A-40 or A-41 , as
described and/or illustrated herein, optionally present (e.g. where chemically possible) as an
agrochemically acceptable salt thereof. In a further alternative yet more particularly
preferable embodiment of the invention (which e.g. can apply to all aspects and/or
embodiments of the invention), the compound of formula (I) is compound A-19, A-21 , A-23,
A-24, A-26, P-3, P-5 or P-7, as described and/or illustrated herein, optionally present (e.g.
where chemically possible) as an agrochemically acceptable salt thereof.
Depending on the nature of the substituents G, R , R2, R3, R4, R5, R6, R7 and R8, compounds
of formula (I) may exist in different isomeric forms. When G is hydrogen, for example,
compounds of formula (I) may exist in different tautomeric forms:
Also, when substituents contain double bonds, cis- and trans-isomers can exist. This
invention covers all such isomers and tautomers and mixtures thereof in all proportions.
These isomers, too, are within the scope of the claimed compounds of the formula (I).
According to a further aspect of the invention, there is provided a compound of formula
wherein:
XX is hydrogen or ethyl; and
R is hydrogen, and R is hydrogen, methyl, Ci-C2alkylthio-CH2CH2- ,
Ci-C 2alkylthio-CH(Me)CH 2- , tetrahydro-2/-/-pyran-4-yl, (tetrahydro-2/-/-pyran-4-yl)-methyl-, or
pyridin-2-yl;
or R and R are methyl;
or R and R taken together are -CH2CH2-0-CH 2CH2- ; and
R4 and R are hydrogen; or R4 and R taken together are -CH2-CH2- ;
provided that when R4 and R taken together are -CH2-CH2- then R and R are
hydrogen; and
G is hydrogen, an agriculturally acceptable metal, or an agriculturally acceptable sulfonium
or ammonium group; or G is -C(0)-R a or -C(0)-0-R ;
wherein Ra is -C6alkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl,
C3-C6cycloalkyl-methyl-, Ci-C4alkoxyCi-C 4alkyl, or phenyl or phenyl substituted by 1, 2 or 3
of, independently, methyl, CifluoroalkyI, methoxy, Cifluoroalkoxy, halogen, cyano or nitro;
and R is C C6alkyl, C2-C3alkenyl-CH2- , C2-C3alkenyl-CH(Me)-, C2-C3alkynyl-CH2- ,
C2-C3alkynyl-CH(Me)-, C3-C6cycloalkyl, C3-C6cycloalkyl-methyl-, Ci-C4alkoxyCi-C 4alkyl, or
phenyl or phenyl substituted by 1, 2 or 3 of, independently, methyl, CifluoroalkyI, methoxy,
Cifluoroalkoxy, halogen, cyano or nitro;
and wherein the compound of formula (ZZ) is optionally present (e.g. where chemically
possible) as an agrochemically acceptable salt thereof.
Preferably, R is hydrogen, and R is hydrogen, Ci-C 2alkylthio-CH (Me)CH2- , (tetrahydro-
2/-/-pyran-4-yl)-methyl-, or pyridin-2-yl;
or R and R are methyl;
or R and R taken together are -CH2CH2 -O-CH2CH2-.
More preferably, R is hydrogen, and R is hydrogen, Ci-C 2alkylthio-CH (Me)CH2- , or
pyridin-2-yl;
or R and R are methyl;
or R and R taken together are -CH2CH2 -O-CH2CH2-.
Most preferably, R and R are hydrogen; or R and R taken together
are -CH2CH2 -O-CH2CH2-.
Preferably, Ra is C C6alkyl. Preferably, R is C C6alkyl.
Preferably, G is hydrogen, an agriculturally acceptable metal, or an agriculturally acceptable
sulfonium or ammonium group. Most preferably, G is hydrogen.
In one particular embodiment, XX is hydrogen. In an alternative particular embodiment, XX
is ethyl.
Preferably, the compound of formula (ZZ) is
optionally present as an agrochemically acceptable salt thereof.
According to a further aspect of the invention, there is provided a method of controlling weeds
in crops of useful plants, comprising applying a compound of formula (ZZ), as defined herein,
or a herbicidal composition comprising such a compound, to the plants or to the locus
thereof. Preferably, the weeds comprise grassy monocotyledonous weeds. More preferably,
the grassy monocotyledonous weeds comprise "warm season" (warm climate) grassy
monocotyledonous weeds, even more preferably weeds from the genus Brachiaria,
Cenchrus, Digitaria, Echinochloa, Eleusine, Eriochloa, Leptochloa, Ottochloa, Panicum,
Pennisetum, Phalaris, Rottboellia, Setaria and/or Sorghum. Preferably, 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.
Typically, the rate of application (typically to the weeds and/or to the crops of useful plants
and/or to the locus thereof) of the compound of formula (ZZ) (which optionally may be an
agrochemically acceptable salt thereof) will be from 1 to 2000 g, in particular from 5 to 1000
g/ha or from 10 to 1000 g/ha or from 10 to 500 g/ha, of the compound of formula (ZZ)
(measured as the salt-free compound, i.e. excluding the weight of any associated salt
counterion(s)). The compound of formula (ZZ) can be applied (typically to the weeds and/or
to the crops of useful plants and/or to the locus thereof) pre- and/or post-emergence, but
preferably is applied post-emergence.
Processes for preparation of compounds, e.g. compounds of formula (I)
Processes for preparation of compounds, e.g. a compound of formula (I) (which optionally
can be an agrochemically acceptable salt thereof), are now described, and form further
aspects of the present invention.
A compound of formula I , wherein G is:
-C(Xa)-Ra, -C(X )-X -R , -C(X )-N(R )-R , -S0 2-Re, -P(Xe)(R )-R9, -CH2-X -Rh; or
phenyl-CH2- or phenyl-CH(Ci-C 2alkyl)- (in each of which the phenyl is optionally substituted
by 1, 2 or 3 of, independently, Ci-C 2alkyl, Cifluoroalkyl, Ci-C 2alkoxy, Cifluoroalkoxy, fluorine,
chlorine, bromine, cyano or nitro), or heteroaryl-CH 2- or heteroaryl-CH(Ci-C 2alkyl)- (in each
of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, Ci-C2alkyl,
Cifluoroalkyl, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or
phenyl-C(0)-CH 2- (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently,
CrC 2alkyl, Cifluoroalkyl, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or
nitro); or CrC 6alkoxy-C(0)-CH 2- , CrC 6alkoxy-C(0)-CH=CH-, C2-C7alken-1-yl-CH 2- ,
C2-C7alken-1-yl-CH(C C2alkyl)-, C2-C4fluoroalken-1-yl-CH 2- , C2-C7alkyn-1-yl-CH 2- , or
C2-C7alkyn-1-yl-CH(C C2alkyl)-;
may be prepared by treating a compound of formula (A), which is a compound of formula I
wherein G is H,
(a) with a reagent G1-Z, wherein G1-Z is an alkylating agent (wherein G 1 is an organic group
according to G within the compound of formula (I) and which is linked by a non-carbonyl,
non-thiocarbonyl carbon atom) such as an organic halide (in which Z = halogen such as
chlorine, bromine or iodine); wherein the organic halide (e.g. chloride) can typically be a

CLAIM
1. A compound of formula (I):
wherein:
X is methyl or chlorine;
R is methyl or chlorine;
R2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine,
CrC 3alkoxy, CrC 2fluoroalkoxy, Ci-C 2alkoxy-Ci-C 3alkoxy-, or dfluoroalkoxy-Ci-C 3alkoxy-;
and
R3, R4, R5 and R6, independently of each other, are hydrogen, CrC 5alkyl, C2-C4alkenyl,
C2-C4alkynyl, C C2fluoroalkyl, Ci-C 3alkoxyCi-C 3alkyl, Ci-C 3alkylthioC C3alkyl,
Ci-C 3alkylsulfinylCrC 3alkyl, Ci-C 3alkylsulfonylCrC 3alkyl; C3-C4cycloalkyl; 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 R3, R4, R5 and R6 is alkenyl, alkynyl, alkoxyalkyl,
alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
or R3 and R4 taken together are -(CH2) 1- or -(CH2) 2-X -(CH2) 3- and R5 and R6 are as
defined herein, or R5 and R6 taken together are -(CH2) 1- or -(CH2) 2-X -(CH2) 3- and R3 and
R4 are as defined herein;
wherein X1 is O, S, S(O), S(0) 2, NH, N(C C2alkyl), N(C C2alkoxy), C(H)(C C2alkyl),
C(C C2alkyl)2 or C(H)(C C2alkoxy);
n 1 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 R4 and R5 taken together are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- or -C(R7 )=C(R7 )-;
wherein R7a is CrC 2alkyl or Ci-C 2alkoxy; and R7 is hydrogen or Ci-C 2alkyl provided that R7
is hydrogen when R7a is CrC 2alkoxy;
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 R7 and R7 independently are hydrogen or Ci-C 2alkyl; and
Y is O, S, S(O), S(0) 2, N(CrC 2alkyl), N(C C2alkoxy), C(O), CR R or -CR 0R CR 2R13- ; and
R8 and R are, independently of each other:
hydrogen, -C6alkyl, C2-C4alkenyl, C2-C4alkynyl, Ci-C 2fluoroalkyl, d-dalkoxyd-
C3alkyl, Ci-C 3alkylthioCi-C 3alkyl, Ci-C 3alkylsulfinylCi-C 3alkyl, or Ci-C 3alkylsulfonylCi-C 3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are Ci-C 3alkyl or Ci-C 2fluoroalkyl; and in which one ring CH2 moiety of a
C4-C6cycloalkyl is optionally replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH,
N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C
C2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being Ci-C 3alkoxy and optionally further
substituted by one substituent being Ci-C 2alkyl;
C5-C6cycloalkenyl or C5-C6cycloalkenyl substituted by one or two d-C 3alkyl
substituents;
d-dcycloalkyld-dalkyl- or d-dcycloalkyld-dalkyl- substituted by one or two ring
substituents which independently are d-C 3alkyl or d-C 2fluoroalkyl; and in which one ring
CH2 moiety of a C4-C6cycloalkyld-C 2alkyl- is optionally replaced by an oxygen or sulfur atom
or by a S(O), S(0) 2, NH, N(d-C 2alkyl), N(Ci-C 2fluoroalkyl), N[C(0)d-dalkyl],
N[C(0)d-dfluoroalkyl] or N(C C2alkoxy) moiety;
C3-C6cycloalkyld-C 2alkyl- substituted by one ring substituent being d-C 3alkoxy and
optionally further substituted by one ring substituent being d-C 2alkyl; or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon, which is
optionally substituted by 1, 2 or 3 ring-carbon substituents independently being d-C 3alkyl,
d-dfluoroalkyl, d-C 3alkyl-C(0)-, Ci-C 2fluoroalkyl-C(0)-, hydroxy (including any oxo
tautomer), C2-C3alkenyl, C2-C3alkynyl, d-dalkoxy, d-dfluoroalkoxy, 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 -C3alkyl, CrC 2fluoroalkyl, C C3alkyl-C(0)-,
C C2fluoroalkyl-C(0)- or Ci-C 2alkyl-S(0) 2- substituent;
provided that no more than one of R8 and R is an optionally substituted cycloalkyl; an
optionally substituted cycloalkyl in which one ring CH2 moiety has been replaced by an
oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl),
N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety; an optionally
substituted cycloalkenyl; an optionally substituted cycloalkyl-alkyl-; an optionally substituted
cycloalkyl-alkyl- in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom
or by a S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety; or Het or Het-CH2- ;
or R8 is hydrogen or C -C2alkyl, and R is C-i-C2alkoxy;
or R8 and R9 taken together are -(CH 2) 7- or -(CH2) 8-X2-(CH 2) 9- ;
wherein X2 is O, S, S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)CrC 2fluoroalkyl], N(C C2alkoxy), C(H)(C C3alkyl), C(C C2alkyl) 2 or
C(H)(Ci-C 3alkoxy);
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 0 , R , R 2 and R 3 are independently of each other hydrogen or C -C4alkyl provided that no
more than one of R 0 , R , R 2 and R 3 is C3-C4alkyl; and
and wherein:
G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or
ammonium group; or
G is -C(Xa)-Ra, -C(X )-X -R , -C(X )-N(R )-R , -S0 2-Re, -P(X e)(R )-R9, -CH2-X -Rh; or
phenyl-CH 2- or phenyl-CH(Ci-C 2alkyl)- (in each of which the phenyl is optionally substituted
by 1, 2 or 3 of, independently, Ci-C 2alkyl, CifluoroalkyI, Ci-C 2alkoxy, Cifluoroalkoxy, fluorine,
chlorine, bromine, cyano or nitro), or heteroaryl-CH 2- or heteroaryl-CH(C -C2alkyl)- (in each
of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, CrC 2alkyl,
C-ifluoroalkyl, CrC 2alkoxy, C-ifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or
phenyl-C(0)-CH 2- (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently,
CrC 2alkyl, C-ifluoroalkyl, C -C2alkoxy, C-ifluoroalkoxy, fluorine, chlorine, bromine, cyano or
nitro); or CrC 6alkoxy-C(0)-CH 2- , CrC 6alkoxy-C(0)-CH=CH-, C2-C7alken-1 -yl-CH2- ,
C2-C7alken-1 -yl-CH(C C2alkyl)-, C2-C4fluoroalken-1 -yl-CH2- , C2-C7alkyn-1 -yl-CH2- , or
C2-C7alkyn-1 -yl-CH(C C2alkyl)-;
wherein Xa, X , X , X , Xe and X are independently of each other oxygen or sulfur; and
wherein
Ra is H, -C2 1alkyl, C2-C2 1alkenyl, C2-C18alkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d -
C10nitroalkyl, d-C 10aminoalkyl, d-C 5alkylamino(d-C 5)alkyl, C2-C8dialkylamino(CrC 5)alkyl,
d-dcycloalkyl(d-d)alkyl, C1-dalkoxy(C 1-d)alkyl, C3-C5alkenyloxy(d-C 5)alkyl, C3-
dalkynyloxy (Crd)alkyl, C1-dalkylthio(C 1-d)alkyl, d-C 5alkylsulfinyl(d-C 5)alkyl, C
dalkylsulfonyl(d-d)alkyl, C2-C8alkylideneaminoxy(CrC 5)alkyl, d-dalkylcarbonyl(dd)
alkyl, C -dalkoxycarbonyl(d-d)alkyl, aminocarbonyl(Ci -C5)alkyl, d -
dalkylaminocarbonyl (Ci -d)alkyl, C2-C8dialkylaminocarbonyl(d-C 5)alkyl, d -
dalkylcarbonylamino(C 1-d)alkyl, /V-(C1-d)alkylcarbonyl-/V-(C 1-d)alkylamino(C 1-d)alkyl,
C3-C6trialkylsilyl(d-C 5)alkyl, phenyl(C -d)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy,
d-C 3alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen , cyano, or nitro), heteroaryl(dd)
alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, d-C 3alkylthio, d-dalkylsulfinyl,
d-dalkylsulfonyl, halogen , cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy,
CrC 3fluoroalkoxy, halogen , cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
of, independently, C -C3 alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, C -C3fluoroalkoxy, halogen,
cyano or nitro;
R is Ci-Ci8alkyl, C3-Ci8alkenyl, C3-Ci8alkynyl, C2-Ci0fluoroalkyl, d-Ciocyanoalkyl, d -
C 0nitroalkyl, C2-Ci0aminoalkyl, C -C5alkylamino(CrC 5)alkyl, C2-C8dialkylamino(Ci -C5)alkyl,
C3-C7cycloalkyl (Ci -C5)alkyl, C -C5alkoxy(CrC 5)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-
C5alkynyloxy(C1-C5)alkyl, C1-C5alkylthio(C1-C5)alkyl, C1-C5alkylsulfinyl(C1-C5)alkyl, C
C5alkylsulfonyl(Ci-C5)alkyl, C2-C8alkylideneaminoxy(Ci-C5)alkyl, d-dalkylcarbonyl(d-
C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C5)alkyl, aminocarbonyl(CrC 5)alkyl, d -
C5alkylaminocarbonyl(Ci-C5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C5)alkyl, d -
C5alkylcarbonylamino(Ci-C5)alkyl, /V-(Ci-C5)alkylcarbonyl-/V-(Ci-C5)alkylamino(Ci-C5)alkyl,
C3-C6trialkylsilyl(Ci-C 5)alkyl, phenyl(CrC 5)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, CrC 3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, Ci-C3fluoroalkoxy,
Ci-C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or nitro), heteroarylddalkyl
(wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, d-dalkyl-thio, d-C 3alkylsulfinyl,
d-dalkylsulfonyl, halogen, cyano, or nitro), C3-C5fluoroalkenyl, d-dcycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, Ci-C3fluoroalkyl, d-dalkoxy,
d-dfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
of, independently, d-d alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen,
cyano or nitro; and
R and R are each independently of each other hydrogen, d-C 10alkyl, d-Ci 0alkenyl, C3-
Cioalkynyl, d-Ci 0fluoroalkyl, Ci-Ciocyanoalkyl, d-Ci 0nitroalkyl, d-d 0aminoalkyl, d -
dalkylamino(d-d)alkyl, d-ddialkylamino(d-d)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl, d -
dalkoxy(d-d)alkyl, d-dalkenyloxy(d-d)alkyl, C3-dalkynyloxy(d-d)alkyl, C
dalkylthio(d-d)alkyl, C1-dalkylsulfinyl(C 1-C5)alkyl, C1-dalkylsulfonyl(C 1-d)alkyl, -
dalkylideneaminoxy(C 1-d)alkyl, C1-dalkylcarbonyl(C 1-C5)alkyl, d-dalkoxycarbonyl(dd)
alkyl, aminocarbonyl(d-d)alkyl, C1-dalkylaminocarbonyl(C 1-d)alkyl, C2-
ddialkylaminocarbonyl(C -d)alkyl, C -dalkylcarbonylamino(C -d)alkyl, /V-(dd)
alkylcarbonyl-/V-(C 2-d)alkylaminoalkyl, C3-C6trialkylsilyl(C -C5)alkyl, phenyl(C C5)alkyl
(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d -
dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, Crdalkylthio, Crdalkylsulfinyl, d -
dalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(d-C 5)alkyl (wherein the heteroaryl is
optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d -
dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen,
cyano, or nitro), d-dfluoroalkenyl, C3-dcycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen,
cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d-dalkyl,
d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
heteroarylamino substituted by 1, 2 or 3 of, independently, -C3alkyl, d-dfluoroalkyl, d -
C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
substituted by 1, 2 or 3 of, independently, CrC 3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, d -
C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen,
cyano or by nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently,
Ci-C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; or C3-
C7cycloalkylamino, di(C3-C7cycloalkyl)amino or C3-C7cycloalkoxy;
or R and R , together with the nitrogen to which they are bonded, to form an unsubstituted 4,
5, 6 or 7 membered ring, optionally containing one heteroatom selected from O or S; and
Re is C -C 0alkyl, C2-C10alkenyl, C2-C10alkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d -
C10nitroalkyl, d-C 10aminoalkyl, C1-dalkylamino(C 1-d)alkyl, d-ddialkylamino(C 1-d)alkyl,
d-dcycloalkyl(d-d)alkyl, d-dalkoxy(d-d)alkyl, d-dalkenyloxy(d-d)alkyl, C3-
dalkynyloxy(d-d)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, C1-dalkylsulfinyl(C 1-d)alkyl, Cr
dalkylsulfonyl(d-d)alkyl, d-dalkylideneaminoxy(C 1-d)alkyl, d-dalkylcarbonyl(dd)
alkyl, C1-dalkoxycarbonyl(C 1-d)alkyl, aminocarbonyl(d-d)alkyl, d -
dalkylaminocarbonyl(Ci-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, d -
C5alkylcarbonylamino(d-C 5)alkyl, /V-(Ci-d)alkylcarbonyl-/V-(Ci-d)alkylamino(Crd)alkyl,
d-dtrialkylsilyl(C -d)alkyl, phenyl(C -d)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy, Crdfluoroalkoxy,
Crdalkylthio, Ci-C3alkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(dd)
alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, Ci-C3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, Crdalkylthio, d-dalkylsulfinyl,
CrC 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of,
independently, d-C 3alkyl, d-C 3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano
or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, CrC 3
alkyl, d-C 3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl,
d-dfluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; phenylamino or
phenylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d -
dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino
substituted by 1, 2 or 3 of, independently, -C3alkyl, d-C 3fluoroalkyl, CrCsalkoxy, Ci-
Csfluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di(C3-C7cycloalkyl)amino,
C3-C7cycloalkoxy, CrCi 0alkoxy, Ci-Ci 0fluoroalkoxy, Ci-C 5alkylamino or di(Ci-C 4alkyl)amino;
R and R9 are are each independently of each other Ci-Ci 0alkyl, C2-Ci 0alkenyl, C2-Ci 0alkynyl,
Ci-Ci 0alkoxy, Ci-Ci 0fluoroalkyl, Ci-Ciocyanoalkyl, CrCi 0nitroalkyl, Ci-Ci 0aminoalkyl, d -
C5alkylamino(Ci-C 5)alkyl, C 2-C8dialkylamino(Ci-C 5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl, d -
C5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(Ci-C 5)alkyl, C3-C5alkynyloxy(Ci-C 5)alkyl, Cr
C5alkylthio(Ci-C 5)alkyl, C1-C5alkylsulfinyl(C -C5)alkyl, Ci-C5alkylsulfonyl(Ci-C 5)alkyl, C2-
C8alkylideneaminoxy(Ci-C 5)alkyl, Ci-C5alkylcarbonyl(Ci-C 5)alkyl, Ci-C5alkoxycarbonyl(d-
C5)alkyl, aminocarbonyl(d-C 5)alkyl, C1-C5alkylaminocarbonyl(C 1-C5)alkyl, C2-
C8dialkylaminocarbonyl(C -C5)alkyl, C -C5alkylcarbonylamino(C -C5)alkyl, /V-(d-
C5)alkylcarbonyl-/V-(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(C 1-C5)alkyl, phenyl(d-C 5)alkyl
(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
C3fluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, d-C 3alkylthio, d-C 3alkylsulfinyl, d -
dalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C -C5)alkyl (wherein the heteroaryl is
optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d -
C3alkoxy, Ci-C 3fluoroalkoxy, Ci-C 3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen,
cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, halogen,
cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d-C 3 alkyl,
CrCsfluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
heteroarylamino substituted by 1, 2 or 3 of, independently, d-C 3 alkyl, d-C 3fluoroalkyl, d -
C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
substituted by 1, 2 or 3 of, independently, d-C 3 alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Ci-
Csfluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
of, independently, d-dalkyl, Crdfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen,
cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, d -
C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro; or C3-
C7cycloalkylamino, di(C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, d-Ci 0fluoroalkoxy, d -
C5alkylamino or di(CrC 4alkyl)amino; or benzyloxy or phenoxy, wherein the benzyl and
phenyl groups are in turn optionally substituted by 1, 2 or 3 of, independently, Ci-C3alkyl, d -
C3fluoroalkyl, Ci-C3alkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; and
Rh is C -C 0alkyl, C3-C10alkenyl, C3-C10alkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d -
C 0nitroalkyl, C2-Cioaminoalkyl, Ci-C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino(Ci-C 5)alkyl,
C 3-C7cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C 5)alkyl, C 3-C5alkenyloxy(Ci-C5)alkyl, C3-
C5alkynyloxy(Ci-C 5)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, Ci-C5alkylsulfinyl(Ci-C 5)alkyl, Cr
C5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(CrC 5)alkyl, d -
C5alkylaminocarbonyl(Ci-C 5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl, d -
dalkylcarbonylamino(d-d)alkyl, /V-(d-d)alkylcarbonyl-/V-(Ci-d)alkylamino(Ci-d)alkyl,
d-dtrialkylsilyl(d-d)alkyl, phenyl(d-d)alkyl (wherein the phenyl is optionally substituted
by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy,
Crdalkylthio, Crdalkylsulfinyl, d-d alkylsulfonyl, halogen, cyano or nitro), heteroaryl(dd)
alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, Crdalkylthio, Crdalkylsulfinyl,
d-C 3 alkylsulfonyl, halogen, cyano or nitro), phenoxy(Crd)alkyl (wherein the phenyl is
optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d -
dalkoxy, d-dfluoroalkoxy, Crdalkylthio, Crdalkylsulfinyl, d-d alkylsulfonyl, halogen,
cyano or nitro), heteroaryloxy(Crd)alkyl (wherein the heteroaryl is optionally substituted by
1, 2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, d-dalkoxy, d-C 3fluoroalkoxy, d -
dalkylthio, Crdalkylsulfinyl, Ci-C3 alkylsulfonyl, halogen, cyano or nitro), C3-
dfluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently,
d-dalkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; or
heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
dfluoroalkyl, d-C 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; CrC 6alkyl-C(0)-; or
phenyl-C(O)- wherein the phenyl is optionally substituted by 1 or 2 of, independently, d -
dalkyl, CifluoroalkyI, d-dalkoxy, dfluoroalkoxy, 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 (e.g. where chemically
possible) as an agrochemically acceptable salt thereof.
2. A 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(Xa)-Ra
or -C(X )-X -R , wherein Xa, Ra, X , X and R are as defined herein.
3. A compound as claimed in claim 1, wherein G is hydrogen, -C(Xa)-Ra or -C(X )-X -R .
4. A compound as claimed in claim 1, 2 or 3, wherein, when G is -C(Xa)-Ra or -C(X )-X -R ,
then Xa, X and X are oxygen, Ra is C C 0alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl
or Ci-C 4alkoxyCi-C 4alkyl; and R is C C 0alkyl, C2-C5alkenyl-CH 2- , C2-C4alkenyl-CH(Me)-,
C2-C5alkynyl-CH 2- , C2-C4alkynyl-CH(Me)-, C3-C6cycloalkyl or Ci-C 4alkoxyC C4alkyl.
5. A compound as claimed in claim 1, 2, 3 or 4, wherein X is methyl.
6. A compound as claimed in claim 1, 2, 3 or 4, wherein X is chlorine.
7. A compound as claimed in claim 1, 2, 3, 4, 5 or 6, wherein R is methyl.
8. A compound as claimed in claim 1, 2, 3, 4, 5 or 6, wherein R is chlorine.
9. A compound as claimed in claim 1, 2, 3 or 4, wherein X is methyl, and R is methyl.
10. A compound as claimed in claim 1, 2, 3 or 4, wherein X is methyl, and R is chlorine.
11. A compound as claimed in any of claims 1 to 10, wherein, when R2 is
or C-ifluoroalkoxy-C-i-Csalkoxy-, then R2 is
R2 0-CH(R 2B)-CH(R2C)-0-;
wherein R2 is C -C2alkyl or C-ifluoroalkyl; and
R2B and R2C are independently hydrogen or methyl, provided that one or both of R2B and R2C
are hydrogen.
12. A compound as claimed in any of claims 1 to 10, wherein R2 is hydrogen, methyl, ethyl,
n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy or
fluoromethoxy.
13. A compound as claimed in any of claims 1 to 10, wherein R2 is methyl, ethyl, ethynyl,
chlorine, methoxy, fluoromethoxy or ethoxy.
14. A compound as claimed in any of claims 1 to 10, wherein R2 is methyl or methoxy.
15. A compound as claimed in claim 1, 2, 3, 4, 5, 6, 7 or 9, wherein:
R is methyl, and R2 is methyl, chlorine or methoxy.
16. A compound as claimed in claim 1, 2, 3, 4, 5, 6, 7 or 9, wherein:
R is methyl, and R2 is methyl.
17. A compound as claimed in claim 1, 2, 3, 4, 5, 6, 8 or 10, wherein:
R is chlorine, and R2 is chlorine or methoxy.
18. A compound as claimed in claim 1, 2, 3, 4, 5, 6, 8 or 10, wherein:
R is chlorine, and R2 is methoxy.
19. A compound as claimed in any of claims 1 to 18, wherein R3, R4, R5 and R6,
independently of each other, are hydrogen, -C3alkyl or C1-C2alkoxyC1-C2alkyl; provided
that no more than one of R3, R4, R5 and R6 is alkoxyalkyl;
or R4 and R5 taken together are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- ;
wherein R7a is C C2alkyl; R7 is hydrogen or C C2alkyl;
n4 is 2 or 3; and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 1 or 2.
20. A compound as claimed in any of claims 1 to 19, wherein R3, R4, R5 and R6,
independently of each other, are hydrogen or C -C2alkyl;
or R4 and R5 taken together are -(CH2) 4- wherein n4 is 2 or 3.
2 1. A compound as claimed in any of claims 1 to 20, wherein:
R8 is hydrogen or Ci-C 2alkyl; and
R9 is:
Ci-C 2alkoxy;
C2-C3alkynyl-CH2- ;
Ci-C 3alkoxyCi-C 3alkyl;
Ci-C 3alkylthioCi-C 3alkyl;
Ci-C 3alkylsulfinylCi-C 3alkyl;
Ci-C 3alkylsulfonylCi-C 3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are CrC 3alkyl or CrC 2fluoroalkyl; and in which one ring CH2 moiety of a
C4-C6cycloalkyl is optionally replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH,
N(CrC 3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C
C2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being Ci-C 3alkoxy and optionally further
substituted by one substituent being Ci-C 2alkyl;
C3-C6cycloalkylmethyl- or C3-C6cycloalkylmethyl- substituted by one or two ring
substituents which independently are C -C3alkyl or C -C2fluoroalkyl; and in which one ring
CH2 moiety of a C4-C6cycloalkylmethyl- is optionally replaced by an oxygen or sulfur atom or
by a S(O), S(0) 2, NH, N(C C2alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety;
C3-C6cycloalkylmethyl- substituted by one ring substituent being C-i-C3alkoxy and
optionally further substituted by one ring substituent being Ci-C 2alkyl; or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon, which is
optionally substituted by 1, 2 or 3 ring-carbon substituents independently being Ci-C 3alkyl,
Ci-C 2fluoroalkyl, Ci-C 3alkyl-C(0)-, CrC 2fluoroalkyl-C(0)-, hydroxy (including any oxo
tautomer), C2-C3alkenyl, C2-C3alkynyl, -C3alkoxy, CrC^luoroalkoxy, 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 C3alkyl, C C2fluoroalkyl, C C3alkyl-C(0)-,
C C2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent;
or R8 and R9 taken together are -(CH2) 7- or -(CH2) 8-X2-(CH2) 9
22. A compound as claimed in any of claims 1 to 20, wherein:
R8 is hydrogen or Ci-C 2alkyl; and
R9 is:
Ci-C 3alkylthioCrC 3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are CrC 3alkyl or CrC 2fluoroalkyl; and in which one ring CH2 moiety of a
C4-C6cycloalkyl is replaced by an oxygen or sulfur atom;
C3-C6cycloalkylmethyl- or C3-C6cycloalkylmethyl- substituted by one or two ring
substituents which independently are CrC 3alkyl or CrC 2fluoroalkyl; and in which one ring
CH2 moiety of a C4-C6cycloalkylmethyl- is replaced by an oxygen or sulfur atom or by a
N[C(0)Ci-C 3alkyl] or N[C(0)C C2fluoroalkyl] moiety; or
Het or Het-CH2- , wherein Het is a heteroaryl, attached at a ring-carbon, which is
optionally substituted by 1, 2 or 3 ring-carbon substituents independently being Ci-C 3alkyl,
Ci-C 2fluoroalkyl, Ci-C 3alkyl-C(0)-, CrC 2fluoroalkyl-C(0)-, hydroxy (including any oxo
tautomer), C2-C3alkenyl, C2-C3alkynyl, CrC 3alkoxy, CrC^luoroalkoxy, 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 CrCsalkyl, d-C^luoroalkyl, d-Caalkyl-C^O)-,
C C2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent;
or R8 and R9 taken together are -(CH2) 7- or -(CH2) 8-X2-(CH2) 9- .
23. A compound as claimed in any of claims 1 to 20, wherein R8 and R are, independently
of each other, hydrogen or C -C3alkyl.
24. A compound as claimed in any of claims 1 to 22, wherein, in R8 and R9, one or both of
R8 and R9 is or are hydrogen; or R8 and R9 taken together
are -(CH2) 7- or -(CH2) 8-X2-(CH2) 9- .
25. A compound as claimed in any of claims 1 to 24, wherein Y is O, S, S(O), S(0) 2, C(O),
CR R or -CR 0R CR 2R 3- .
26. A compound as claimed in any of claims 1 to 24, wherein Y is O or CR R9.
27. A compound as claimed in any of claims 1 to 24, wherein Y is CR R9.
28. A compound as claimed in any of claims 1 to 24, wherein Y is CH2.
29. A compound as claimed in any of claims 1 to 24, wherein
Y is CR R9; and
R4 and R5 are taken together and are -(CH2) 4- or -(CH2) 5-C(R7a)(R7 )-(CH2) 6- ;
wherein R7a is CrC 2alkyl; R7 is hydrogen or Ci-C2alkyl;
n4 is 2 or 3; and
n5 and n6 are independently 0, 1 or 2 provided that n5 + n6 is 1 or 2.
30. A compound as claimed in claim 29, wherein Y is CH2.
3 1. A compound as claimed in claim 29 or 30, wherein R3 and R6, independently of each
other, are hydrogen or C -C2alkyl; and R4 and R5 taken together are -(CH2) 4- wherein n4 is 2
or 3.
32. A compound as claimed in any of claims 1 to 3 1, wherein the compound of formula (I) is
a compound of one of the following types, described and illustrated below, optionally present
as an agrochemically acceptable salt thereof:
- 235 -
wherein:
R is methyl, X is methyl, and R2 is hydrogen, methyl, chlorine, methoxy, ethynyl, ethyl, vinyl,
2-methoxyethoxy or ethoxy; or
R is chlorine, X is methyl, and R2 is hydrogen, chlorine, methoxy, ethynyl, ethyl, vinyl,
2-methoxyethoxy or ethoxy; or
R is methyl, X is chlorine, and R2 is hydrogen, methyl, chlorine, methoxy, ethynyl, ethyl,
vinyl, 2-methoxyethoxy or ethoxy; or
R is chlorine, X is chlorine, and R2 is hydrogen, chlorine, methoxy, ethynyl, ethyl, vinyl,
2-methoxyethoxy or ethoxy.
33. A compound as claimed in any of claims 1 to 3 1 which is compound A-1 , A-2, A-3, A-4,
A-5, A-6, A-7, A-8, A-9, A-10, A-1 1, A-12, A-13, A-14 or A-15, as illustrated below, optionally
present as an agrochemically acceptable salt thereof:
34. A compound as claimed in any of claims 1 to 3 1 which is compound A-1 6, A-1 7 or A-1 8,
as illustrated below, optionally present as an agrochemically acceptable salt thereof:
35. A compound as claimed in any of claims 1 to 3 1 which is compound A-20, A-22, A-25,
A-27, A-28, A-30, A-31 , A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40 or A-41 , as
illustrated below, optionally present as an agrochemically acceptable salt thereof:
36. A compound as claimed in any of claims 1 to 3 1 which is compound A-19, A-21 , A-23,
A-24, A-26, A-29, P-3, P-4, P-5 or P-7, as illustrated below, optionally present as an
agrochemically acceptable salt thereof:
37. A herbicidal composition which comprises a compound of formula (I), as defined in any
of claims 1 to 36, and an agrochemically acceptable carrier, diluent and/or solvent.
38. A herbicidal composition according to claim 37, which comprises one or more further
herbicides and/or a safener.
39. A method of controlling weeds in crops of useful plants, comprising applying a
compound of formula (I), as defined in any of claims 1 to 36, or a herbicidal composition
comprising such a compound, to the plants or to the locus thereof.
40. A method as claimed in claim 39, wherein the weeds comprise grassy
monocotyledonous weeds.
4 1. A method as claimed in claim 40, wherein the grassy monocotyledonous weeds
comprise weeds from the genus Brachiaria, Cenchrus, Digitaria, Echinochloa, Eleusine,
Eriochloa, Leptochloa, Ottochloa, Panicum, Pennisetum, Phalaris, Rottboellia, Setaria and/or
Sorghum.
42. A method as claimed in claim 39, 40 or 4 1, 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.
43. A compound of formula (ZZ):
wherein:
XX is hydrogen or ethyl; and
R is hydrogen, and R is hydrogen, methyl, C1-C2alkylthio-CH2CH2- ,
C1-C2alkylthio-CH(Me)CH 2- , tetrahydro-2/-/-pyran-4-yl, (tetrahydro-2/-/-pyran-4-yl)-methyl-, or
pyridin-2-yl;
or R and R are methyl;
or R and R taken together are -CH2CH2-0-CH 2CH2- ; and
R4 and R are hydrogen; or R4 and R taken together are -CH2-CH2- ;
provided that when R4 and R taken together are -CH2-CH2- then R and R are
hydrogen; and
G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium
or ammonium group; or G is -C(0)-R a or -C(0)-0-R ;
wherein Ra is CrCealkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl,
C3-C6cycloalkyl-methyl-, d-C^lkoxyCr^alkyl, or phenyl or phenyl substituted by 1, 2 or 3
of, independently, methyl, CifluoroalkyI, methoxy, Cifluoroalkoxy, halogen, cyano or nitro;
and FT is Ci-C 6alkyl, C2-C3alkenyl-CH2- , C2-C3alkenyl-CH(Me)-, C2-C3alkynyl-CH2- ,
C 2-C3alkynyl-CH(Me)-, C3-C6cycloalkyl, C3-C6cycloalkyl-methyl-, Ci-C4alkoxyCi-C 4alkyl, or
phenyl or phenyl substituted by 1, 2 or 3 of, independently, methyl, CifluoroalkyI, methoxy,
C-ifluoroalkoxy, halogen, cyano or nitro;
and wherein the compound of formula (ZZ) is optionally present (e.g. where chemically
possible) as an agrochemically acceptable salt thereof.
) is
optionally present as an agrochemically acceptable salt thereof.