Herbicidally active (alkynyl-phenyl)-substituted cyclic dione compounds and
derivatives thereof
The present invention relates to herbicidally active (alkynyl-phenyl)-substituted cyclic
dione compounds, in particular pyrandione, thiopyrandione, piperidinedione,
cyclopentanedione, cyclohexanedione, cyclohexanetrione or cycloheptanedione compounds,
and derivatives thereof (e.g. enol ketone tautomer derivatives thereof and/or fused and/or
bicyclic derivatives thereof as appropriate), 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.
WO 01/17972 A2 (Syngenta Participations AG) discloses (4-methyl-phenyl)-substituted
(such as 4-methyl-2,6-diethyl-phenyl- substituted) carbocycles or heterocycles, in particular
carbocyclic or heterocyclic diones, suitable for use as herbicides.
WO 03/01 3249 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. In WO 03/013249 A 1 and US 2005/0054535 A 1, the
cyclic ketoenol (whose tautomer is a cyclic dione) can in particular be a 3-(substitutedphenyl)-
pyrrolidine-2,4-dione, a 3-(substituted-phenyl)-tetrahydrofuran-2,4-dione, a 3-
(substituted-phenyl)-pyran-2,4-dione derivative, a 2-(substituted-phenyl)-cyclopentane-1 ,3-
dione, or a 2-(substituted-phenyl)-cyclohexane-1 ,3-dione, et al., or a derivative (e.g. ester or
carbonate derivative) of these cyclic ketoenols / cyclic diones.
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 and/or phosphonium salt to boost activity. In WO
2007/068427 A2 and US 2009/0227563 A 1, the cyclic ketoenol (whose tautomer is a cyclic
dione) can in particular be a 3-(substituted-phenyl)-pyrrolidine-2,4-dione, a 3-(substitutedphenyl)-
tetrahydrofuran-2,4-dione, a 3-(substituted-phenyl)-pyran-2,4-dione derivative, a 2-
(substituted-phenyl)-cyclopentane-l ,3-dione, or a 2-(substituted-phenyl)-cyclohexane-1 ,3-
dione, a 4-(substituted-phenyl)-pyrazolidine-3,5-dione, et al., or a derivative (e.g. ester or
carbonate derivative) of these cyclic ketoenols / cyclic diones.
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) , which can e.g. be a heteroatom-X-containing-spirocyle, at
the 5-position of the cyclohexane-1 ,3-dione, and having herbicidal properties. WO
2010/081689 A2 (Bayer CropScience AG) discloses the use of 2-(substituted-phenyl)-5-
[R -X-(CR 6R7) -]-cyclohexane-1 ,3-dione compounds or derivatives (i.e. compounds
substantially as disclosed in WO 2008/1 10308) as insecticides and/or acaricides and/or
fungicides.
WO 2008/1 10307 A 1 (Syngenta Participations AG) discloses 2-(substituted-phenyl)-5-
(carbon-linked-heterocyclyl)-cyclohexane-1 ,3-dione compounds and derivatives, and their
use as herbicides. WO 201 0/081 687 A 1 (Bayer CropScience AG) discloses the use of 2-
(substituted-phenyl)-5-(carbon-linked-heterocyclyl)-cyclohexane-1 ,3-dione compounds or
derivatives (i.e. compounds substantially as disclosed in WO 2008/1 10307) as insecticides
and/or acaricides and/or fungicides.
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.
Cyclopentane-1 ,3-dione compounds substituted at the 2-position by substituted-phenyl
and having herbicidal activity are described, for example, in WO 2010/000773 A 1,WO
2010/069834 A 1,WO 2010/089210 A 1,WO 2010/102848 A 1 and WO 201 1/007146 A 1 (all
Syngenta Limited et al.); and in e.g. WO 01/74770 (Bayer AG). For example, WO
2010/000773 A 1 (Syngenta Limited) discloses 5-(heterocyclylalkyl)-3-hydroxy-2-
phenylcyclopent-2-en-1-one compounds and certain derivatives thereof as herbicides. WO
201 1/073060 A2 (Syngenta Participations AG) discloses a method of combating and
controlling insects, acarines, nematodes or moluscs comprising applying a WO 2010/000773
compound. Also, for example, WO 2010/069834 A 1 (Syngenta Limited) discloses
cyclopentane-1 ,3-diones having both heteroarylmethyl- and
2-(substituted-phenyl)- substituents on the cyclopentane ring, and derivatives thereof
containing latentiating groups; these compounds are disclosed as having herbicidal
properties. Fused bicyclic and oxygen-bridged cyclopentanedione derivatives, specifically
10-oxatricyclo-[5.2.1 .02,6]decane-3,5-diones and derivatives, which are substituted by
substituted-phenyl and which have herbicidal activity, are disclosed in WO 2009/019005 A2
and WO 2009/019015 A 1 (both Syngenta Limited). Phenyl-substituted fused bicyclooctane-
1,3-dione derivatives, and their use as pesticides and/or herbicides, are disclosed in WO
2010/040460 A2 (Bayer Cropscience AG).
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 at the 2-position by (specifically) either
methyl or chlorine, 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 post-emergence.
Certain cyclic 1,3-dione compounds (wherein one carbonyl ring-carbon is defined as
being the 1-position of the cycle / ring) and derivatives (e.g. fused such as fused bicyclic
derivatives, and/or spirocyclic derivatives) thereof, which are substituted at the 2-position of
the cyclic 1,3-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) either fluorine or
bromine, and derivatives of the enol ketone tautomer of such cyclic 1,3-diones, which have
herbicidal activity and/or plant-growth-inhibiting properties, especially in the control of grassy
monocotyledonous weeds and/or when used post-emergence, have now been found, which
are encompassed by the present invention.
The present invention is based on the finding that cyclic diones of the general formula (I)
wherein:
X is methyl or chlorine (preferably methyl);
R is fluorine or bromine (preferably fluorine);
R2 is ethynyl, d-Csalkoxy-, d-Cshaloalkoxy-, or d-Csalkoxy-CrCsalkoxy- (preferably
-0-R 2 , wherein R2 is methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl,
or -CH2CH2OCH 3; more preferably -0-R 2 , wherein R2 is methyl, ethyl, trifluoromethyl or
difluoromethyl); and
Q is a pyran-3,5-dione-4-yl, a thiopyran-3,5-dione-4-yl, a piperidine-3,5-dione-4-yl, a
cyclopentane-1 ,3-dione-2-yl, a cyclohexane-1 ,3,5-trione-2-yl, a cyclohexane-1 ,3-dione-2-yl,
or a cycloheptane-1 ,3-dione-2-yl, or a derivative thereof (e.g. a fused such as fused bicyclic
derivative, and/or a spirocyclic derivative, and/or an enol ketone tautomer derivative thereof),
wherein Q is as further defined herein, are novel;
and that the exemplified compounds A8, A9, A10 and A16 (and also A14 for SETFA and
ZEAMX weeds) within this formula (I) and disclosed herein appear to be potent postemergent
herbicides when used against grassy (in particular warm climate grassy)
monocotyledonous weeds, when applied at about 250 g/ha post-emergence (e.g. as shown
in Biological Examples 1 and 2 hereinafter).
Also, the results in Biological Example 1A hereinafter appear to show that Compound A14,
within the present formula (I), having a 2-fluoro-6-methoxy-4 -(prop - 1-ynyl )-phenyl moiety
attached to the 2-position of a oxygen-containing-spirocyclic cyclohexane-1 ,3-dione, is a
more potent herbicide against the grassy monocotyledonous weeds ALOMY (Alopecurus
myosuroides) and ZEAMX (Zea mays, corn, e.g. volunteer corn), and perhaps also SETFA
(Setaria faberi), than compound B2 which has a 2-fluoro-6-methoxy-4 -ethynyl-phenyl moiety
attached to the 2-position of the same oxygen-containing-spirocyclic cyclohexane-1 ,3-dione,
when applied post-emergence at 250 g/ha under the conditions stated in Biological Example
1A.
Also, the exemplified Compound A8 within the present formula (I), e.g. when applied at 30
g/ha post-emergence appear to exhibit a low or reasonably low phytotoxicity against certain
docotyledonous crops, in particular soybean and/or sugarbeet (e.g. see Biological Example 2
hereinafter); see also Biological Example 3 for the low phytotoxicity of Compound A8 on
soybean. Finally, Compound A8 within the present formula (I) appear to exhibit a medium or
reasonably low phytotoxicity against wheat relative to their (generally higher) herbicidal
activity (phytotoxicity) against warm-climate grassy monocotyledonous weeds, e.g. when
applied post-emergence (e.g. see Biological Example 2 hereinafter).
Thus, in a first aspect of the invention, there is provided a compound of formula (I):
wherein:
X is methyl or chlorine;
R is fluorine or bromine;
R2 is ethynyl, Ci -C3alkoxy-, Ci -C3haloalkoxy- (in particular Ci -C3fluoroalkoxy-), or
CrCaalkoxy-CrCaalkoxy-;
and Q is a group of either formula Q 1 or Q2:
wherein in Q 1:
R3, R4 and R5, independently of each other, are hydrogen, -C5alkyl (e.g. CrC 4alkyl, e.g.
C C2alkyl), C2-C4 alkenyl (e.g. C2-C3alkenyl-CH 2- , e.g. ethenyl-CH 2-), C2-C4alkynyl (e.g.
C2-C3alkynyl-CH 2- , e.g. ethynyl-CH 2-), C C2fluoroalkyl or Ci-C 3alkoxyCi-C 3alkyl; and R6 is
hydrogen; CrC 5alkyl (in particular Ci-C 4alkyl, e.g. Ci-C 2alkyl); C2-C4 alkenyl (in particular C2-
C3alkenyl-CH 2- , e.g. ethenyl-CH 2-); C2-C4alkynyl (preferably C2-C3alkynyl-CH 2- , more
preferably ethynyl-CH 2-); R6 CºC-CH2- ; C C2fluoroalkyl; Ci-C 3alkoxyC C3alkyl;
Ci-C 3alkylthioC C3alkyl; Ci-C 3alkylsulfinylC C3alkyl; Ci-C 3alkylsulfonylC C3alkyl; C3-
C4cycloalkyl (in particular cyclopropyl); or an unsubstituted 4, 5 or 6 (in particular 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
(preferably tetrahydrofuranyl such as tetrahydrofuran-3-yl, or tetrahydropyranyl such as
tetrahydropyran-4-yl);
or R6 is T-(CH 2)m-CH(R 7)-, wherein m is 0 or 1 (preferably m is 0), and either R7 is
hydrogen or R7 and R5 together are a bond, and T is an optionally substituted heterocyclyl as
defined below;
or R6 is Het-CH(R 8)-, wherein either R8 is hydrogen or R8 and R5 together are a bond,
and Het is an optionally substituted heteroaryl as defined below;
or R6 is Cs-CecycloalkylCrC^alkyl- (in particular C3-C6cycloalkylmethyl-); or is
CU-CecycloalkylCrC^alkyl- (in particular C4-C6cycloalkylmethyl-) substituted, at a cycloalkyl
ring-carbon atom which is not the ring-carbon atom attached to the -C -C2alkyl- moiety and
which is not bonded directly to the ring-carbon atom attached to the -C -C2alkyl- moiety, by
one or two ring substituents which independently are: =N-0-R 0 , oxo (=0), C-i-C4alkoxy,
CrC^haloalkoxy, 2-(C 1-C3alkoxy)-ethoxy, C3-C5cycloalkyloxy, (C3-C5cycloalkyl)methoxy,
C2-C3alkenyl-CH 2-oxy, C -C3alkyl or C -C2fluoroalkyl; or benzyloxy in which the phenyl ring is
optionally substituted by one or two substituents independently being C -C3alkyl,
CrC 2fluoroalkyl, C C3alkyl-C(0)-, C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E,
S(0) 2R6E, -S(0) 2-R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) ,
C2-C3alkynyl, -CºC-R6 , C C3alkoxy, C C2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-,
HCºC-CH2-0-, halogen, cyano or nitro;
or R6 is benzyl optionally substituted on its phenyl ring by one or two substituents which
independently are: C C3alkyl, C C2fluoroalkyl, C C3alkyl-C(0)-,
CrC 2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E, -S(0) 2-R6E, -N(R6 )(R6G) ,
hydroxy, C2-C3alkenyl, -C(R )=C(R )(R ) , C2-C3alkynyl, -CºC-R , Ci-C 3alkoxy, C
C2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro, 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) 1- or -(CH2) 2-X -(CH2) 3- and R3 and R4 are as
defined herein (e.g. hereinabove);
or R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
or -CH(R )-C(R20)(R2 )-CH(R22)-;
T is a 4 to 7 membered monocyclic or an 8 to 11 membered fused bicyclic heterocyclyl,
having one or two ring heteroatoms independently selected from oxygen, sulfur and nitrogen;
and wherein the heterocyclyl T is optionally substituted by 1 or 2 ring-carbon substituents
independently being -C3alkyl (preferably Ci-C2alkyl), d-C^luoroalkyl (preferably
dfluoroalkyl), -SC C3alkyl, -S(0)C C3 alkyl, -S(0) 2Ci.C3alkyl, or oxo (=0), and/or is
optionally substituted by one C1-C4alkyl, Ci-C 2fluoroalkyl, C1-C4alkoxy, d-dfluoroalkoxy; or
a R -C(0)- or a C -C2alkyl-S(0) 2- 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; and wherein
Het is a heteroaryl, attached at a ring-carbon, which is optionally substituted by 1, 2 or
3 (preferably 1 or 2, more preferably 1) ring-carbon substituents independentlybeing
-C3alkyl, Ci-C 2fluoroalkyl, d-C 3alkyl-C(0)-, d-C 2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) ,
SR6E, S(0)R 6E, S(0) 2R6E, -S(0) 2-R6E, -N(R6 )(R6G) , hydroxy,
d-dalkenyl, -C(R6BB)=C(R6C )(R6C2) , d-dalkynyl, -CºC-R6 , d-dalkoxy, C
dfluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro;
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 d-C 3alkyl, d-C 2fluoroalkyl,
d-dalkyl-C(O)-, d-C 2fluoroalkyl-C(0)- or d-C 2alkyl-S(0) 2- substituent;
wherein:
R6 is dfluoroalkyl (preferably trifluoromethyl), fluorine, chlorine or bromine;
R6B, R6C and R6CC independently are hydrogen, methyl, dfluoroalkyl (preferably
trifluoromethyl), fluorine or chlorine; provided that R6B, R6C and R6CC in total contain no more
than one carbon atom, and R6B, R6C and R6CC in total comprise no more than one chlorine;
and
R , R and R independently are hydrogen, methyl, dfluoroalkyl (preferably
trifluoromethyl), fluorine or chlorine; provided that R6BB , R6C and R6C2 in total contain no more
than one carbon atom, and R6BB , R6C and R6C2 in total comprise no more than one chlorine;
and provided that -C(R6BB)=C(R6C )(R6C2) is not C2-C3alkenyl; and
R6D and R6E independently are CrC 3alkyl (preferably CrC 2alkyl such as methyl),
Cifluoroalkyl (preferably trifluoromethyl), or -N(R6 )(R6 ) ;
R6 is -C(0)-CrC 2alkyl (preferably -C(O)-methyl), -C(0)-Cifluoroalkyl
(preferably -C(O)-trifluoromethyl), -S(0) 2-CrC 2alkyl
(preferably -S(0) 2-methyl), -S(0) 2-Cifluoroalkyl (preferably -S(0) 2-trifluoromethyl), C C2alkyl
(preferably methyl), or Cifluoroalkyl (preferably trifluoromethyl);
R6G and R6 independently are hydrogen, methyl or Cifluoroalkyl (preferably
trifluoromethyl); and
R6 is hydrogen, C -C2alkyl (preferably methyl), or Cifluoroalkyl (preferably
trifluoromethyl);
and wherein R is C -C4alkyl (e.g. methyl, ethyl, n-propyl, isopropyl or n-butyl),
C2-C4alkenyl attached at a carbon atom partaking in the C=C double bond (e.g. Me2C=CH-),
C -C2fluoroalkyl (e.g. CF3 or CHF2CF2-), C -C2alkoxymethyl- (e.g. methoxymethyl-),
CrC 3alkoxy (e.g. methoxy), cyclopropyl, furanyl (e.g. furan-2-yl or furan-3-yl), morpholin-4-yl,
isoxazol-3-yl, 5-methyl-isoxazol-3-yl, pyrazol-5-yl, 3-methylpyrazol-5-yl, 1-methylpyrazol-5-yl,
1,3-dimethylpyrazol-5-yl; or phenyl or phenyl substituted by 1 or 2 substituents independently
being methyl, ethyl, Cifluoroalkyl, methoxy, C-ifluoroalkoxy, fluorine, chlorine, SC -C3alkyl
(preferably SMe), S(0)C C3alkyl (preferably S(O)Me) or S(0) 2C C3alkyl (preferably
S(0) 2Me);
wherein R 0 is hydrogen, C -C4alkyl (e.g. methyl), C -C2fluoroalkyl,
2-(C 1-C3alkoxy)-ethyl, C3-C5cycloalkyl or (C3-C5cycloalkyl)methyl;
wherein X1 is O, S, S(O), S(0) 2, NH, N(C C3alkyl), N(C C3alkoxy), C(H)(C C2alkyl),
C(C C2alkyl)2, C(H)(C C3alkoxy) or C(Me)(C C2alkoxy); and
n 1 is 2, 3, 4 or 5 (e.g. 3, 4 or 5); and n2 and n3 are independently 1, 2 or 3 provided
that n2 + n3 is 2, 3 or 4;
wherein: R and R 8 are both hydrogen, or R and R 8 are taken together and form
an -O- or -Ci-C 2alkylene- bridge; and
R 2 and R 7 are independently hydrogen, C C3alkyl or Ci-C 2alkoxyC C2alkyl;R 13 , R 4
and R 5 are independently hydrogen, Ci-C 3alkyl or Ci-C 2alkoxyCrC 2alkyl, provided that one,
two or all of R 3 , R 4 and R 5 are hydrogen; and
R 6 is hydrogen; -C3alkyl; C1-C2alkoxyC1-C2alkyl; phenyl optionally substituted by 1,
2 or 3 (in particular 1 or 2) of, independently, being CrC 3alkyl, CrC 2fluoroalkyl,
CrC 3alkyl-C(0)-, C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E, -S(0) 2-
R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) , C2-C3alkynyl, -CºC-R6 ,
Ci-C3alkoxy, Ci-C2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HCºC-CH2-0-, halogen,
cyano or nitro; or a 5-membered or 6-membered heteroaryl, attached at a ring-carbon and
optionally substituted by 1, 2 or 3 (in particular 1 or 2) ring-carbon substituents independently
being C C3alkyl, C C2fluoroalkyl, C C3alkyl-C(0)-,
CrC 2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E, -S(0) 2-R6E, -N(R6 )(R6G) ,
hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) , C2-C3alkynyl, -CºC-R6 , C C3alkoxy, C
C2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro;
and wherein:
R and R22 are independently hydrogen, C -C3alkyl or d-dalkoxyd-dalkyl;
and R20 and R2 are independently hydrogen, C -C3alkyl or d-dalkoxyd-dalkyl;
or R20 and R2 taken together are oxo (=0), =N-0-R 0 , or =CH2;
or R20 and R2 , together with the carbon atom to which they are attached, form a 5, 6 or
7 (in particular 5 or 6) membered saturated heterocyclyl, wherein the heterocyclyl has two
ring heteroatoms independently being oxygen or sulfur and which are not directly bonded to
each other, and wherein the heterocyclyl is optionally substituted by 1, 2 or 3 (e.g. 1 or 2)
ring-carbon substituents independently being C -C2alkyl (e.g. methyl);
and wherein in Q2:
R33, R34 , R35 and R36, independently of each other, are hydrogen, d-dalkyl (in
particular C1-C4alkyl, e.g. d-dalkyl), C2-C4 alkenyl (in particular C2-C3alkenyl-CH2- , e.g.
ethenyl-CH2-), C2-C4 alkynyl (in particular C2-C3alkynyl-CH2- , e.g. ethynyl-CH 2-), d -
dfluoroalkyl, d-dalkoxyd-dalkyl, d-C 3alkylthiod-C 3alkyl, d-C 3alkylsulfinyld-C 3alkyl,
d-C 3alkylsulfonyld-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, said heterocyclyl being 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 R , R , R and R is alkenyl,
alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or
heterocyclyl;
or R33 and R34 taken together are -(CH2 )n3i- or -(CH2 )n32-X -(CH2 )n33- and R35 and R36 are as
defined herein (e.g. hereinabove), or R35 and R36 taken together
are -(CH2 ) n3i- or -(CH2)n32-X -(CH2 ) 33- and R33 and R34 are as defined herein (e.g.
hereinabove);
wherein X3 1 is O, S, S(O), S(0) 2, NH, N(C C2alkyl), N(C C2alkoxy), C(H)(CrC 2alkyl),
C(Ci-C 2alkyl)2 or C(H)(C C2alkoxy);
n31 is 2, 3, 4 or 5 (in particular 4 or 5); and
n32 and n33 are independently 1, 2 or 3 provided that n32 + n33 is 2, 3 or 4 (in
particular 3 or 4);
or R34 and R35 taken together are -C(R 7 )=C(R 7 )-;
wherein R 7 and R 7 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 -
C R 310 R 3 11C R 312R 313_.
R38 and R3 are, independently of each other: hydrogen, Ci-C 6alkyl (in particular d -
C4alkyl, e.g. Ci-C 2alkyl), C2-C4alkenyl (in particular C2-C3alkenyl-CH2- , e.g. ethenyl-CH2-), C2-
C4alkynyl (in particular C2-C3alkynyl-CH2- , e.g. ethynyl-CH 2-), Ci-C 2fluoroalkyl, d -
C3alkoxyCi-C 3alkyl, Ci-C 3alkylthioCi-C 3alkyl, Ci-C 3alkylsulfinylCi-C 3alkyl, or C
C3alkylsulfonylCi-C 3alkyl; C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two
substituents which independently are Ci-C 3alkyl (in particular methyl or ethyl) or d -
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(C1-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 -C3alkoxy (in particular -C2alkoxy)
and optionally further substituted by one substituent being d-C 2alkyl (in particular methyl);
d-dcycloalkenyl or d-dcycloalkenyl substituted by one or two d-dalkyl (in particular
methyl) substituents; C3-C6cycloalkyld-C 2alkyl- (in particular d-C 6cycloalkylmethyl-) or C3-
dcycloalkyld-dalkyl- (in particular d-C 6cycloalkylmethyl-) substituted by one or two ring
substituents which independently are d-dalkyl or d-C 2fluoroalkyl, and in which one ring
CH2 moiety of a C4-C6cycloalkyld-C 2alkyl- (in particular d-C 6cycloalkylmethyl-) is optionally
(e.g. preferably) replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(ddalkyl),
N(C C2fluoroalkyl), N[C(0)d-C 3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy)
moiety; C3-C6cycloalkylC 1-C2alkyl- (in particular C3-C6cycloalkylmethyl-) substituted by one
ring substituent being CrC 3alkoxy (in particular CrC 2alkoxy) and optionally further
substituted by one ring substituent being CrC 2alkyl (in particular methyl); or HetA or
HetA-CH2- ;
wherein HetA 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
Ci-C3alkyl, C C2fluoroalkyl, C C3alkyl-C(0)-, C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) ,
SR6E, S(0)R 6E, -S(0) 2-R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) ,
C2-C3alkynyl, -CºC-R6 , C C3alkoxy, C C2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-,
HCºC-CH2-0-, halogen, cyano or nitro; 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 R38 and R3 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)Ci-C 3alkyl], 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 HetA or HetA-CH2- ;
or R38 is hydrogen or C -C2alkyl (in particular H or Me), and R3 is C -C2alkoxy (in
particular methoxy);
or R38 and R39 taken together are -(CH2)n37- or -(CH2)n38-X 2-(CH2)n39- ;
wherein X32 is O, S, S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl),
N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl], N(C C2alkoxy), C(H)(C C3alkyl), C(C C2alkyl)2
or C(H)(Ci-C 3alkoxy);
n37 is 2, 3, 4, 5 or 6 (in particular 4 or 5); and
n38 and n39 are independently 0, 1, 2 or 3 provided that n38 + n39 is 2, 3, 4 or 5 (in
particular 3 or 4); and
R3 0 , R3 , R3 2 and R3 3 are independently of each other hydrogen or C C4alkyl (in
particular C C2alkyl) provided that no more than one of R3 0, R3 , R3 2 and R3 3 is C3-C4alkyl;
and wherein:
R6 , R6BB , R6C , R6C2, R6E, R6 , R6G, R6 and R6 are as defined hereinabove for when
Q is Q 1; and
and wherein in Q 1 or Q2:
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(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(Ci-C 2alkyl)- (in each
of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, Ci-C2alkyl,
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,
Ci-C 2alkyl, CifluoroalkyI, Ci-C 2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or
nitro); or Ci-C 6alkoxy-C(0)-CH 2- , C C6alkoxy-C(0)-CH=CH-, C2-C7alken-1-yl-CH2- ,
C2-C7alken-1-yl-CH(Ci-C 2alkyl)-, C2-C4fluoroalken-1-yl-CH 2- , C2-C7alkyn-1-yl-CH 2- , or
C2-C7alkyn-1-yl-CH(C C2alkyl)-;
wherein Xa, X , X , X , Xe and X are independently of each other oxygen or sulfur ( in
particular oxygen); and wherein
Ra is H, C -C2ialkyl, C2-C2ialkenyl, C2-Ci 8alkynyl, Ci-Ci 0fluoroalkyl, Ci-Ci 0cyanoalkyl,
Ci-Ci 0nitroalkyl, Ci-Ci 0aminoalkyl, C -C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino(Ci-
C5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl, C -C5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(Ci-C 5)alkyl,
C3-C5alkynyloxy(Ci-C 5)alkyl, C -C5alkylthio(Ci-C 5)alkyl, C1-C5alkylsulfinyl(C 1-C5)alkyl, C
C5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, C -C5alkylcarbonyl(Ci-
C5)alkyl, C -C5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(Ci-C 5)alkyl, C
C5alkylaminocarbonyl(Ci-C 5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl, C
C5alkylcarbonylamino(Ci-C 5)alkyl, /V-(Ci-C5 )alkylcarbonyl-/V-(Ci-C5)alkylamino(Ci-C 5)alkyl,
C 3-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, C i -C3alkoxy, C i -C3fluoroalkoxy,
C i -C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(Ci-
C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, -
C3alkyl, C i -C3fluoroalkyl, C i -C3alkoxy, C i -C3fluoroalkoxy, C i -C3alkylthio, CrC 3alkylsulfinyl,
CrC 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, -C3alkyl, d-dfluoroalkyl, d-dalkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
of, independently, CrC 3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, C -C3fluoroalkoxy, halogen,
cyano or nitro;
R is CrCi 8alkyl, C3-Ci 8alkenyl, C3-Ci 8alkynyl, C2-Ci 0fluoroalkyl, C -Ciocyanoalkyl, d -
Cionitroalkyl, C2-Ci 0aminoalkyl, d-dalkylamino (Ci -d)alkyl, C2-C8dialkylamino(Ci -C5)alkyl,
d-dcycloalkyl (Ci -d)alkyl, C -dalkoxy(d-d)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-
C5alkynyloxy(d-C 5)alkyl, C -C5alkylthio(Ci -C5)alkyl, C -C5alkylsulfinyl(Ci -C5)alkyl, d -
dalkylsulfonyl(d-d)alkyl, C2-C8alkylideneaminoxy(Ci -C5)alkyl, CrC 5alkylcarbonyl(Cr
d)alkyl, C -dalkoxycarbonyl(d-d)alkyl, aminocarbonyl(d-d)alkyl, d -
dalkylaminocarbonyl(d-d)alkyl, C2-C8dialkylaminocarbonyl(Crd)alkyl, d -
dalkylcarbonylamino(C -d)alkyl, /V-(C -d)alkylcarbonyl-/V-(C -d)alkylamino(C -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-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy, d-C 3fluoroalkoxy,
Crdalkylthio, C -C3alkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or nitro), heteroarylddalkyl
(wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-C 3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, Crdalkylthio, CrC 3alkylsulfinyl,
C -C3alkylsulfonyl, halogen, cyano, or nitro), C3-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, C -C3fluoroalkyl, d-C 3alkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen,
cyano or nitro; and
R and R are each independently of each other hydrogen, CrC 0alkyl, C3-C 0alkenyl,
C3-C10alkynyl, C2-C10fluoroalkyl, d-C 10cyanoalkyl, d-C 10nitroalkyl, CrC 10aminoalkyl, d -
C5alkylamino(CrC 5)alkyl, C2-C8dialkylamino(CrC 5)alkyl, C3-C7cycloalkyl(CrC 5)alkyl, d -
C5alkoxy(C -C5)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-C5alkynyloxy(CrC 5)alkyl, Cr
C5alkylthio(C -C5)alkyl, Ci-C5alkylsulfinyl(C -C5)alkyl, C -C5alkylsulfonyl(C -C5)alkyl, C2-
C8alkylideneaminoxy(CrC 5)alkyl, C -C5alkylcarbonyl(CrC 5)alkyl, CrC 5alkoxycarbonyl(Cr
C5)alkyl, aminocarbonyl(CrC 5)alkyl, C -C5alkylaminocarbonyl(CrC 5)alkyl, C2-
C8dialkylaminocarbonyl(CrC 5)alkyl, C -C5alkylcarbonylamino(CrC 5)alkyl, /V-(d-
C5)alkylcarbonyl-/V-(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(CrC 5)alkyl, phenyl(Cr C5)alkyl
(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
C3fluoroalkyl, C -C3alkoxy, C -C3fluoroalkoxy, Crdalkylthio, d-C 3alkylsulfinyl, d -
C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl (Ci -C5)alkyl (wherein the heteroaryl is
optionally substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, d-C 3fluoroalkyl, Ci-
Csalkoxy, CrC 3fluoroalkoxy, CrC 3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen,
cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
of, independently, Ci-C 3alkyl, CrC 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen,
cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl,
Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
heteroarylamino substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, d -
C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, d -
C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
of, independently, Ci-C 3alkyl, CrCsfluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, halogen,
cyano or by nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently,
CrC 3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, 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, 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 d-Cioalkyl, C2-Ci 0alkenyl, C2-Ci 0alkynyl, d-Ci 0fluoroalkyl, d-Ciocyanoalkyl, d -
Cionitroalkyl, d-Cioaminoalkyl, Ci-C 5alkylamino(CrC 5)alkyl, C 2-C8dialkylamino(CrC 5)alkyl,
C3-C7cycloalkyl(CrC 5)alkyl, Ci-C 5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-
C5alkynyloxy(Ci-C 5)alkyl, Ci-C 5alkylthio(Ci-C 5)alkyl, Ci-C 5alkylsulfinyl(Ci-C 5)alkyl, d -
C5alkylsulfonyl(CrC 5)alkyl, C2-C8alkylideneaminoxy (CrC 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, CrC 5alkoxycarbonyl (CrC 5)alkyl, aminocarbonyl(CrC 5)alkyl, d -
C5alkylaminocarbonyl(CrC 5)alkyl, C2-C8dialkylaminocarbonyl (CrC 5)alkyl, d -
C5alkylcarbonylamino(CrC 5)alkyl, /V-(CrC 5)alkylcarbonyl-/V-(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, d-C 3alkoxy, CrC 3fluoroalkoxy,
Ci-C 3alkylthio, Ci-C 3alkylsulfinyl, Ci-C 3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(d-
C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, Ci-C 3alkylthio, Ci-C 3alkylsulfinyl,
Ci-C 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy,
CrC 3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of,
independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano
or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, d -
C3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C -C3alkyl,
C -C3fluoroalkyl, C -C3alkoxy, C -C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or
phenylamino substituted by 1, 2 or 3 of, independently, C -C3alkyl, CrC 3fluoroalkyl, -
C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino
substituted by 1, 2 or 3 of, independently, C -C3alkyl, C -C3fluoroalkyl, C -C3alkoxy, d -
C3fluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di(C3-C7cycloalkyl)amino,
C3-C7cycloalkoxy, CrCi 0alkoxy, Ci-Ci0fluoroalkoxy, C -C5alkylamino or di(Ci -C4alkyl)amino;
R and R9 are are each independently of each other CrCi 0alkyl, C2-Ci 0alkenyl, C2-
C10alkynyl, d-doalkoxy, d-dofluoroalkyl, d-docyanoalkyl, d-donitroalkyl, C
C10aminoalkyl, C1-dalkylamino(C 1-d)alkyl, d-ddialkylamino(C 1-d)alkyl, C3-
dcycloalkyl(d-d)alkyl, C1-dalkoxy(C 1-d)alkyl, d-dalkenyloxy(d-d)alkyl, C3-
dalkynyloxy(d-d)alkyl, C1-dalkylthio(C 1-d)alkyl, C1-dalkylsulfinyl(C 1-d)alkyl, C
dalkylsulfonyl(d-d)alkyl, d-dalkylideneaminoxy(d-d)alkyl, d-dalkylcarbonyl(d-
C5)alkyl, C1-dalkoxycarbonyl(C 1-d)alkyl, aminocarbonyl(d-d)alkyl, d -
dalkylaminocarbonyl(d-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, d -
dalkylcarbonylamino (Ci -d)alkyl, /V-(d-d)alkylcarbonyl-/V-(d-d)alkylaminoalkyl, C3-
C6trialkylsilyl (Ci -C5)alkyl, phenyl(d-d)alkyl (wherein the phenyl is optionally substituted by
1, 2 or 3 of, independently, d-C 3alkyl, C -C3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, C
dalkylthio, C -C3alkylsulfinyl, d-C 3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(Cr
d)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d -
C3alkyl, C -C3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, d-C 3alkylthio, d-dalkylsulfinyl,
Crdalkylsulfonyl, halogen, cyano, or nitro), d-dfluoroalkenyl, d-C 8cycloalkyl; phenyl or
phenyl substituted by 1, 2 or 3 of, independently, d-C 3alkyl, C -C3fluoroalkyl, Crdalkoxy,
Crdfluoroalkoxy, 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, d -
C3alkyl, C -C3fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, d-dalkyl,
d-C 3fluoroalkyl, d-dalkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; phenylamino or
phenylamino substituted by 1, 2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, C
dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino
substituted by 1, 2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, Crdalkoxy, d -
C3fluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di(C3-C7cycloalkyl)amino,
C3-C7cycloalkoxy, Ci-Ci 0fluoroalkoxy, Ci-C 5alkylamino 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-C 3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen,
cyano or nitro; and
Rh is Ci-Ci 0alkyl, C3-Ci 0alkenyl, C3-Ci 0alkynyl, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, -
C 0nitroalkyl, C2-Ci 0aminoalkyl, Ci-C 5alkylamino(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-C 5alkylthio(Ci-C 5)alkyl, Ci-C 5alkylsulfinyl(Ci-C 5)alkyl, Cr
C5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, CrC 5alkylcarbonyl(Cr
C5)alkyl, C1-C5alkoxycarbonyl(C 1-C5)alkyl, aminocarbonyl(C 1-C5)alkyl, C
C5alkylaminocarbonyl(C 1-C5)alkyl, C2-C8dialkylaminocarbonyl(C 1-C5)alkyl, C
C5alkylcarbonylamino(C -C5)alkyl, /V-(C -C5 )alkylcarbonyl-/V-(C -C5)alkylamino(C -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, CrC 3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy,
CrC 3alkylthio, CrC 3alkylsulfinyl, C -C3alkylsulfonyl, halogen, cyano or nitro), heteroaryl(Cr
C5)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, Ci-C 3alkylthio, CrC 3alkylsulfinyl,
CrC 3alkylsulfonyl, halogen, cyano or nitro), phenoxy(CrC 5)alkyl (wherein the phenyl is
optionally substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, C
C3alkoxy, C -C3fluoroalkoxy, CrC 3alkylthio, CrCsalkylsulfinyl, CrC 3alkylsulfonyl, halogen,
cyano or nitro), heteroaryloxy(C -C5)alkyl (wherein the heteroaryl is optionally substituted by
1, 2 or 3 of, independently, Ci-C 3alkyl, CrC 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, C
C3alkylthio, CrCsalkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano or nitro), C3-C5fluoroalkenyl,
C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Cr
C3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or
heteroaryl substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, Ci-C 3fluoroalkyl, Cr
C3alkoxy, 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, -
C2alkyl, CifluoroalkyI, CrC 2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro;
and 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, ierf-butyl, n-pentyl, neopentyl, or n-hexyl. The alkyl groups can e.g. be CrC 6alkyl
groups (except where already defined more narrowly), but are preferably CrC 4alkyl or -
C3alkyl groups (except where already defined more narrowly), and, more preferably, are
C1-C2alkyl 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.
Fluoroalkyl 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. Fluoroalkyl is typically C
C3fluoroalkyl or C1-C2fluoroalkyl (preferably Cifluoroalkyl), such as CF3, CHF2, CH2F,
CH3CHF-, CF3CH2- , CHF2CH2- , CH2FCH2- , CHF2CF2- or (CH3)2CF-. Fluoroalkoxy is
typically CrCsfluoroalkoxy or d-C^luoroalkoxy (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 heteroaryl rings will contain 1, 2 or 3 ring heteroatoms and/or bicyclic
heteroaryl systems will contain 1, 2, 3 or 4 ring heteroatoms, each of 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 d-Csalkyl (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. C -C2alkyl or C -C2fluoroalkyl) 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 cycloalkyl 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.
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.
Preferred quaternary ammonium bases suitable for salt formation correspond, for
example, to the formula [N(Ra R R Rd)]OH, wherein Ra, R , R and R are each
independently of the others hydrogen, C -C4alkyl. Further suitable tetraalkylammonium bases
with other anions can be obtained, for example, by anion exchange reactions.
Preferred tertiary sulfonium bases suitable for salt formation correspond, for example,
to the formula [SReRfRg]OH, wherein Re, Rf and Rg are each independently of the others C
C4alkyl. 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.
It should be understood that in those compounds of formula I , where G is a metal,
ammonium or sulfonium as mentioned above and as such represents a cation, the
corresponding negative charge is largely delocalised across the 0-C=C-C=0 unit.
The compounds of formula I according to the invention also include hydrates which
may be formed during the salt formation.
The latentiating groups (i.e. leaving or removeable groups) within G (for example,
without limitation, the latentiating groups where G is -C(Xa)-Ra or -C(X )-X -R , et al.) 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) 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,
carbonate and/or thiocarbonate 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 (non-phytotoxicity) on
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, Y, R , R2, R2 , R6 , R6BB, R6C , R6C2, R6D,
R , Re, R , R9, Rh, Xa, X , X , X , Xe, X , Q, T, V, Het, HetA, X1, X3 1 , X32, n1, n2 , n3, n31 , n32,
n33, n37, n38, and/or n39, 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. For the avoidance of doubt, preferred,
suitable and/or particular features can be combined together with preferred, suitable and/or
particular features with different levels of ranking (e.g. with different levels of preference).
In one particular embodiment of the invention, X is chlorine. However, in the present
invention, most preferably, X is methyl.
In the present invention, most preferably, R is fluorine. In a further preferable
embodiment of the invention, R is bromine.
Therefore, most preferably, X is methyl, and R is fluorine, for all aspects and/or
embodiments of the invention. 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 bromine.
As described above, R2 is ethynyl, -C3alkoxy-, CrC 3haloalkoxy- (in particular -
C3fluoroalkoxy-), or Ci-C 3alkoxy-Ci-C 3alkoxy-.
In one embodiment, R2 is ethynyl.
Preferably, R2 is -0-R 2 , wherein R2 is C C3alkyl, C C3haloalkyl (in particular C
C3fluoroalkyl), or d-Csalkoxy-CrCsalkyl-. Where R2 is C C3alkyl, R2 being methyl or ethyl
is preferred. Where R2 is C -C3haloalkyl, R2 being C -C3fluoroalkyl is preferred (more
preferably C -C2fluoroalkyl, even more preferably C-ifluoroalkyl). Where R2 is C -C3haloalkyl
or C -C3fluoroalkyl, more specifically, R2 being trifluoromethyl, difluoromethyl, or
trifluoroethyl (e.g. 2,2,2-trifluoroethyl) is especially preferred, most particularly trifluoromethyl
or difluoromethyl. Where R2 is Ci-C 3alkoxy-C C3alkyl-, -CH2CH2OCI-l3 (i.e. 2-methoxyethyl-
) is preferred. In these preferred embodiments, preferably R is fluorine and/or X is methyl.
Therefore, more preferably, in all aspects and/or embodiments of the invention, R2 is
-0-R 2 , wherein R2 is methyl, ethyl, C -C2fluoroalkyl (in particular trifluoromethyl,
difluoromethyl, or trifluoroethyl such as 2,2,2-trifluoroethyl), or -CH2CH2OCH3 (i.e. 2-
methoxyethyl-). In this more preferred embodiment, preferably R is fluorine and/or X is
methyl.
Even more preferably, in all aspects and/or embodiments of the invention, R2 is
-0-R 2 , wherein R2 is methyl, ethyl or C-ifluoroalkyl, in particular methyl, ethyl,
trifluoromethyl or difluoromethyl. In these even more preferred embodiments, preferably R
is fluorine and/or X is methyl.
Most preferably, in all aspects and/or embodiments of the invention, R2 is -0-R 2 ,
wherein R2 is methyl. In this most preferred embodiment, preferably R is fluorine and/or X
is methyl.
Therefore, most preferably, in all aspects and/or embodiments of the invention, X is
methyl, R is fluorine, and R2 is -0-R 2 wherein R is methyl.
Preferably, e.g. in all aspects and/or embodiments of the invention, 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 , -S0 2-Re, or -CH2-
X -Rh; wherein Xa, X , X , X , Ra, R , Re and Rh are as defined herein .
More preferably, e.g. in all aspects and/or embodiments of the invention , 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, e.g. in all aspects and/or embodiments of the invention, Xa, X , X , X , Xe
and/or X are oxygen; and/or X is sulfur.
More preferably, Xa, X , X , Xe and X are oxygen; and X is oxygen or sulfur. Even
more preferably, Xa, X , X , X , Xe and X are oxygen.
Preferably, Ra is C C10alkyl (e.g. C C6alkyl), C2-C6alkenyl (e.g. C2-C4alkenyl), C2-
C6alkynyl (e.g. C2-C4alkynyl), C3-C6cycloalkyl or Ci-C4alkoxyCrC 4alkyl. Alternatively,
preferably, Ra is d-dcycloalkyldalkyl; or phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or
2) of, independently, d-dalkyl (e.g. dalkyl), d-dfluoroalkyl (e.g. dfluoroalkyl), d -
dalkoxy (e.g. dalkoxy), d-C 3fluoroalkoxy (e.g. dfluoroalkoxy), halogen (e.g. fluorine,
chlorine or bromine), cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 (e.g. 1
or 2) of, independently, d-dalkyl (e.g. dalkyl), d-C 3fluoroalkyl (e.g. dfluoroalkyl), d -
dalkoxy (e.g. dalkoxy), d-C 3fluoroalkoxy (e.g. dfluoroalkoxy), halogen (e.g. fluorine,
chlorine or bromine), or cyano (in which the heteroaryl preferably consists of a single ring).
More preferably, Ra is d-d 0alkyl (e.g. d-C 6alkyl), C2-C6alkenyl (e.g. C2-C4alkenyl),
C2-dalkynyl (e.g. C2-C4alkynyl), d-C 6cycloalkyl, d-dalkoxyd-dalkyl,
d-dcycloalkyldalkyl ; or phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or 2) of,
independently, d-C 3alkyl (e.g. dalkyl), d-C 3fluoroalkyl (e.g. dfluoroalkyl), d-C 3alkoxy
(e.g. dalkoxy), d-C 3fluoroalkoxy (e.g. dfluoroalkoxy), halogen (e.g. fluorine, chlorine or
bromine), cyano or nitro.
Preferably, R is d-d 0alkyl (e.g. d-dalkyl), C2-C5alkenyl-CH2- (e.g.
C2-C3alkenyl-CH2-), C2-C4alkenyl-CH(Me)- (e.g. d-dalkenyl-CH(Me)-),
C2-C5alkynyl-CH2- (e.g. d-dalkynyl-CH 2-), C2-dalkynyl-CH(Me)- (e.g.
C2-C3alkynyl-CH(Me)-), C3-C6cycloalkyl or C1-C4alkoxyC1-C4alkyl. Alternatively, preferably,
R is C3-C7cycloalkylCialkyl; or phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or 2) of,
independently, -C3alkyl (e.g. Cialkyl), Ci-C3fluoroalkyl (e.g. Cifluoroalkyl), Ci-C 3alkoxy
(e.g. Cialkoxy), Ci-C 3fluoroalkoxy (e.g. Cifluoroalkoxy), halogen (e.g. fluorine, chlorine or
bromine), cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 (e.g. 1 or 2) of,
independently, Ci-C 3alkyl (e.g. Cialkyl), Ci-C3fluoroalkyl (e.g. Cifluoroalkyl), Ci-C 3alkoxy
(e.g. Cialkoxy), Ci-C 3fluoroalkoxy (e.g. Cifluoroalkoxy), halogen (e.g. fluorine, chlorine or
bromine), or cyano (in which the heteroaryl preferably consists of a single ring).
More preferably, R is C Ci0alkyl (e.g. C C6alkyl), C2-C5alkenyl-CH2- (e.g.
C2-C3alkenyl-CH2-), C2-C4alkenyl-CH(Me)- (e.g. C2-C3alkenyl-CH(Me)-),
C2-C5alkynyl-CH2- (e.g. C2-C3alkynyl-CH2-), C2-C4alkynyl-CH(Me)- (e.g.
C2-C3alkynyl-CH(Me)-), C3-C6cycloalkyl, Ci-C4alkoxyC C4alkyl, C3-C7cycloalkylCialkyl; or
phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or 2) of, independently, Ci-C3alkyl (e.g.
Cialkyl), Ci-C 3fluoroalkyl (e.g. Cifluoroalkyl), Ci-C 3alkoxy (e.g. Cialkoxy), Ci-C3fluoroalkoxy
(e.g. Cifluoroalkoxy), halogen (e.g. fluorine, chlorine or bromine), cyano or nitro.
Preferably, Re is Ci-Ci 0alkyl (e.g. Ci-C6alkyl or Ci-C alkyl), Ci-Ci 0fluoroalkyl (e.g. C
C3fluoroalkyl); or phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or 2) of, independently, C
C3alkyl (e.g. Cialkyl), Ci-C3fluoroalkyl (e.g. Cifluoroalkyl), Ci-C 3alkoxy (e.g. Cialkoxy), C
C3fluoroalkoxy (e.g. Cifluoroalkoxy), halogen (e.g. fluorine, chlorine or bromine), cyano or
nitro.
Preferably, Rh is Ci-Ci 0alkyl (e.g. Ci-C6alkyl or Ci-C alkyl), Ci-Ci 0fluoroalkyl (e.g. C
C3fluoroalkyl) or C C6alkyl-C(0)- (e.g. C C4alkyl-C(0)-). In particular, Re is C C 0alkyl (e.g.
C C6alkyl or C C4alkyl).
When G is -C(Xa)-Ra or -C(X )-X -R , then preferably Xa and X are oxygen, and X is
oxygen or sulfur, Ra is Ci-Ci 0alkyl (e.g. Ci-C6alkyl), C2-C6alkenyl (e.g. C2-C alkenyl), C2-
C6alkynyl (e.g. C2-C alkynyl), C3-C6cycloalkyl or Ci-C alkoxyCi-C alkyl; and R is Ci-Ci 0alkyl
(e.g. C C6alkyl), C2-C5alkenyl-CH2- (e.g. C2-C3alkenyl-CH2-), C2-C4alkenyl-CH(Me)- (e.g.
C2-C3alkenyl-CH(Me)-), C2-C5alkynyl-CH2- (e.g. C2-C3alkynyl-CH2-),
C2-C4alkynyl-CH(Me)- (e.g. C2-C3alkynyl-CH(Me)-), C3-C6cycloalkyl or Ci-C4alkoxyC C4alkyl.
In a further particular embodiment, G is hydrogen, or 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. More preferably, G is hydrogen, or
an agriculturally acceptable alkali metal or alkaline earth metal (e.g. lithium, sodium,
potassium, magnesium or calcium). Most preferably G is hydrogen.
Particularly preferably, in all aspects and/or embodiments of the invention,
Q is a group of formula Q 1, or
Q is a group of formula Q2 and Y is O.
Most preferably, in all aspects and/or embodiments of the invention, Q is a group of
formula Q 1.
Where Q is a group of formula Q 1 as defined herein e.g. hereinabove, a compound of
formula (I) has the general structure (1-1 ) :
Preferably, R3, R4 and/or R5, independently of each other, are hydrogen, C -C4alkyl
(e.g. C C2alkyl), C2-C3alkenyl-CH2- (e.g. ethenyl-CH2-), C2-C3alkynyl-CH2- (e.g.
ethynyl-CH2-), d-C^luoroalkyl (e.g. dfluoroalkyl) or d-dalkoxyCrdalkyl;
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;
or R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
or -CH(R )-C(R20)(R2 )-CH(R22)- (preferably -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)
- or -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-).
More preferably, R3, R4 and/or R5, independently of each other, are hydrogen or d -
C2alkyl (in particular hydrogen);
or R3 and R4 taken together are -(CH2)ni- or -(CH2 )n2 -X -(CH2 )n3- and R5 and R6 are as
defined herein, or R5 and R6 taken together are -(CH2)ni- or -(CH2) 2-X -(CH2) 3- and R3 and
R4 are as defined herein;
or R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
or -CH(R )-C(R20)(R2 )-CH(R22)- (preferably -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)
- or -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-).
Still more preferably, R3, R4 and R5 are hydrogen;
or R3 and R5 are hydrogen, and R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
, or -CH(R )-C(R20)(R2 )-CH(R22)-.
Yet more preferably, R3, R4 and R5 are hydrogen; or R3 and R5 are hydrogen, and R4
and R6 taken together are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)- or
-C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-.
Most preferably, R3, R4 and R5 are hydrogen.
Preferably, when R6 is benzyl optionally substituted on its phenyl ring by one or two
substituents, these substituents are independently:
cyano, -CºC-R6 , -C(R6B)=C(R6C)(R6CC) , -C(0)-R 6D, -S(0) 2-R6E, C C3alkoxy (preferably
CrC 2alkoxy such as methoxy), CrC^luoroalkoxy (preferably Cifluoroalkoxy), halogen
(preferably fluorine or chlorine), methyl or C-ifluoroalkyl, wherein R6 is hydrogen, methyl,
ethyl, C-ifluoroalkyl (preferably trifluoromethyl), fluorine, chlorine or bromine and R6B, R6C,
R6CC, R6D, and R6E are as defined herein.
When R6 is optionally substituted benzyl, then, more preferably still, R6 is benzyl
substituted on its phenyl ring by a first substituent being:
cyano, -CºC-R6 , -C(R6B)=C(R6C)(R6CC) or -C(0)-R 6D; and optionally substituted on its phenyl
ring by a second independent substituent being:
cyano, -CºC-R6 , -C(R6B)=C(R6C)(R6CC) , -C(0)-R 6D, -S(0) 2-R6E, C C2alkoxy (preferably
methoxy), CrC 2fluoroalkoxy (preferably Cifluoroalkoxy), halogen (preferably fluorine or
chlorine), or methyl; in which R6D and R6E independently are methyl or trifluoromethyl.
When R6 is optionally substituted benzyl, then, even more preferably, R6 is benzyl
substituted on its phenyl ring by a first substituent being: cyano or -CºC-R6 ; and optionally
substituted on its phenyl ring by a second independent substituent being:
cyano, -CºC-R , -C(R )=C(R )(R ) , -C(0)-R , -S(0) 2-R , methoxy, dfluoroalkoxy,
fluorine, chlorine, or methyl; in which R6D and R6E independently are methyl or trifluoromethyl.
When R6 is optionally substituted benzyl, then, still more preferably, R6 is benzyl
substituted on its phenyl ring by one substituent being cyano or -CºC-R6 .
Preferably, R6 is: hydrogen; CrC 4alkyl (e.g. CrC 2alkyl); C2-C3alkenyl-CH 2- (e.g.
ethenyl-CH 2-); C2-C3alkynyl-CH 2- (preferably ethynyl-CH 2- , which is alternatively named
propargyl); Ci-C 2fluoroalkyl (e.g. Cifluoroalkyl); Ci-C 2alkoxyCrC 2alkyl;
Ci-C 2alkylthioC C2alkyl; C -C2alkylsulfinylC 1-C2alkyl; Ci-C 2alkylsulfonylC C2alkyl;
cyclopropyl; or tetrahydrofuranyl (such as tetrahydrofuran-3-yl), or tetrahydropyranyl (such as
tetrahydropyran-4-yl);
or R6 is T-CH(R7)- (in particular, R7 can be hydrogen);
or R6 is Het-CH(R8)- (in particular, R8 can be hydrogen);
or R6 is C3-C6cycloalkylmethyl- (e.g. cyclohexylmethyl-); or is
C4-C6cycloalkylmethyl- (e.g. cyclohexylmethyl-) substituted, at a cycloalkyi ring-carbon atom
which is not the ring-carbon atom attached to the -C -C2alkyl- moiety and which is not
bonded directly to the ring-carbon atom attached to the -C -C2alkyl- moiety, by one ring
substituent being =N-0-R 0 , oxo (=0), CrC 3alkoxy, Cihaloalkoxy, cyclopropyloxy,
(cyclopropyl)methoxy or vinyl-CH 2-oxy, and optionally by a second ring substituent being
CrC 2alkyl (e.g. methyl);
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;
or R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
, or -CH(R )-C(R20)(R2 )-CH(R22)-.
More preferably, R6 is: hydrogen; CrC 4alkyl (in particular Ci-C 2alkyl);
C2-C3alkynyl-CH 2- (preferably ethynyl-CH 2- , which is alternatively named propargyl); or
Ci-C 2alkoxyCrC 2alkyl (in particular methoxymethyl);
or R6 is T-CH(R7)- (in particular, R7 can be hydrogen);
or R6 is Het-CH(R8)- (in particular, R8 can be hydrogen);
or R6 is cyclohexylmethyl- substituted, at the 4-position of the cyclohexyl ring
(calculated with respect to the ring-carbon atom attached to the -methyl- moiety), either by
one ring substituent being =N-0-R 0 ; or by a first ring substituent being oxo (=0),
CrC 3alkoxy, Cihaloalkoxy, cyclopropyloxy, (cyclopropyl)methoxy or vinyl-CH 2-oxy, and
optionally by a second ring substituent being CrC 2alkyl (in particular methyl);
or R3 and R4 taken together are -(CH2)nr or -(CH2 )n2 -X -(CH2 )n3- 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;
or R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
, or -CH(R )-C(R20)(R2 )-CH(R22)-.
Still more preferably, R6 is: hydrogen; C -C4alkyl (in particular C -C2alkyl);
C2-C3alkynyl-CH 2- (preferably ethynyl-CH 2- , which is alternatively named propargyl); or
C -C2alkoxyC -C2alkyl (in particular methoxymethyl);
or R6 is T-CH(R7)- (in particular, R7 can be hydrogen);
or R6 is Het-CH(R8)- (in particular, R8 can be hydrogen);
or R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-
, or -CH(R )-C(R20)(R2 )-CH(R22)-.
Still more preferably, R6 is hydrogen, CrC 4alkyl (in particular Ci-C 2alkyl), or
C2-C3alkynyl-CH 2- (preferably ethynyl-CH 2- , which is alternatively named propargyl);
or R4 and R6 taken together are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-
or -C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-.
Still more preferably, R6 is hydrogen, C -C4alkyl, or C2-C3alkynyl-CH 2-.
Still more preferably, R6 is hydrogen, C -C2alkyl, or C2-C3alkynyl-CH 2- .
Yet more preferably, R6 is hydrogen, or ethynyl-CH 2- , and most preferably R6 is
ethynyl-CH 2- , which is alternatively named propargyl).
Preferably, T is a 4 to 7 (e.g. 4, 5 or 6, preferably 5 or 6) membered monocyclic
heterocyclyl, having one or two (preferably one) ring heteroatoms independently selected
from oxygen, sulfur and nitrogen; and wherein the heterocyclyl T is optionally substituted by
1 or 2 ring-carbon substituents independently being Ci-C 3alkyl (in particular Ci-C 2alkyl),
Ci-C 2fluoroalkyl (in particular CifluoroalkyI) or oxo (=0), and/or is optionally substituted by
one CrC 4alkyl (in particular Ci-C 3alkyl or Ci-C 2alkyl), Ci-C 2fluoroalkyl (in particular
CifluoroalkyI), -C4alkoxy (in particular Ci-C 3alkoxy or Ci-C 2alkoxy), Ci-C 2fluoroalkoxy (in
particular C-ifluoroalkoxy), R -C(0)- or C -C2alkyl-S(0) 2- 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.
More preferably,T is a 4 to 7 (e.g. 4, 5 or 6, preferably 5 or 6) membered monocyclic
heterocyclyl, having one or two (preferably one) ring heteroatoms independently selected
from oxygen, sulfur and nitrogen; and wherein the heterocyclyl T is optionally substituted by
one CrC 4alkyl (in particular -C3alkyl or CrC 2alkyl), CrC 2fluoroalkyl (in particular
Cifluoroalkyl), Ci-C4alkoxy (in particular CrC 3alkoxy or Ci-C2alkoxy), Ci-C2fluoroalkoxy (in
particular C-ifluoroalkoxy), R -C(0)- or Ci-C2alkyl-S(0) 2- 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.
Still more preferably,T is a 4 to 7 (e.g. 4, 5 or 6, preferably 5 or 6) membered
monocyclic heterocyclyl, having one ring heteroatom independently selected from oxygen,
sulfur and nitrogen; and wherein the heterocyclyl T is optionally substituted by one
R -C(0)- or CrC 2alkyl-S(0) 2- (preferably R -C(0)-) 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.
Most preferably, T is a 4, 5 or 6 (preferably 5 or 6) membered monocyclic heterocyclyl,
having one ring heteroatom independently selected from oxygen and nitrogen; and wherein
the heterocyclyl T is optionally substituted by one R -C(0)- or Ci-C2alkyl-S(0) 2- (preferably
R -C(0)-) substituent on a ring nitrogen if present.
It is particularly preferred that T is attached at a ring carbon atom to
the -(CH2)m-CH(R7)- or -CH(R7)- moiety.
It is particularly preferred that, in T, the one or two (e.g. one) ring heteroatoms are not
directly bonded to the ring atom (e.g. ring carbon atom) which is the position of attachment to
the -(CH2)m-CH(R7)- or -CH(R7)- moiety.
In T, preferably, when there are two ring heteroatoms, then they are separated by one
or (preferably) two carbon atoms (i.e. they are not directly bonded to each other).
Preferably, R9 is Ci-C4alkyl (in particular methyl, ethyl, n-propyl, isopropyl or n-butyl,
preferably methyl, ethyl, n-propyl or isopropyl), Ci-C2fluoroalkyl (e.g. CF3 or CHF2CF2-),
Ci-C2alkoxymethyl- (e.g. methoxymethyl-), or cyclopropyl.
More preferably, R9 is CrC 3alkyl (preferably methyl or ethyl), Ci-C2fluoroalkyl (e.g. CF3
or CHF2CF2-), methoxymethyl-, or cyclopropyl.
Most preferably, R9 is methyl, ethyl, C C2fluoroalkyl (e.g. CF3 or CHF2CF2-) or
methoxymethyl-; in particular methyl.
Preferably, T is one of the following sub-formulae T , T2, T3, T4, T5, T6, T7, T33, T34 , T37,
T38, 4 , T42, T43, T44, T47, T8 , T89, 90 or T107
T5)
(Te) (T ) (Te) (T )
wherein: A is the position of attachment to the -(CH2)m-CI-l(R7)- or -CH(R7)- moiety; and
R is as defined herein.
More preferably, T is one of the sub-formulae T , T2, T4, T6, T7, T33, T34 , T4 1, T42, T43,
T44, T87, T89 or T90. Even more preferably, T is one of the sub-formulae T2, T6, T7, T33, T34 ,
T4 , T42, T43, T44, T87, T89 or T90. Yet more preferably, T is one of the sub-formulae T2, T7, T87
or T90. Further more preferably, T is one of the sub-formulae T2, T7 or T90. Most preferably, T
is sub-formula T7.
Preferably, R8 is hydrogen.
Preferably, Het is a heteroaryl, attached at a ring-carbon, which is optionally substituted
by 1, 2 or 3 (preferably 1 or 2, more preferably 1) ring-carbon substituents independently
being d-dalkyl (preferably C1-C2alkyl), C1-C2fluoroalkyl (preferably dfluoroalkyl),
CrC 3alkyl-C(0)- (preferably Cialkyl-C(O)- which is methyl-C(O)-),
CrC 2fluoroalkyl-C(0)- (preferably Cifluoroalkyl-C(O)-), hydroxy (including any oxo tautomer),
C2-C3alkenyl (preferably ethenyl or prop-1-enyl), C2-C3alkynyl (preferably ethynyl or prop-1-
ynyl), CrC 3alkoxy (preferably CrC 2alkoxy, such as Ci-C2alkoxy which is methoxy), d -
C2fluoroalkoxy (preferably Cifluoroalkoxy), halogen (preferably fluorine or chlorine), cyano or
nitro; 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, Ci-C 2fluoroalkyl,
Ci-C 3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent.
More preferably, 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) ringcarbon
substituents independently being Ci-C2alkyl, dfluoroalkyl, Ci-C2alkyl-C(0)-,
dfluoroalkyl-C(O)-, -SCi-C2alkyl, hydroxy (including any oxo tautomer), ethynyl, prop-1-ynyl,
C-i-C2alkoxy, C .C2fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro,; 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 Ci-C3alkyl, CrC 2fluoroalkyl, Ci-C3alkyl-C(0)-,
Ci-C2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent.
Even more preferably, Het is a heteroaryl (in particular monocyclic heteroaryl),
attached at a ring-carbon, which is optionally substituted by 1 or 2 (in particular 1) ringcarbon
substituents independently being C -C2alkyl (in particular methyl), C1-C2alkoxy (in
particular methoxy), dfluoroalkyl (in particular CF3) , d-dfluoroalkoxy, d-dalkyl-C(O)- (in
particular Me-C(O)-), dfluoroalkyl-C(O)-, ethynyl, prop-1-ynyl, d-dfluoroalkoxy, fluorine,
chlorine or cyano; and/or, in the case of a 5-membered heteroaryl ring containing a ringnitrogen
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 (e.g. methyl), dfluoroalkyl, methyl-C(O)- or dfluoroalkyl-C(O)- substituent.
Still more preferably, 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 d-C 2alkyl (in particular methyl), dfluoroalkyl (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 ring-nitrogen atom not partaking in a C=N ring double bond by one methyl
substituent.
Preferably, Het is an optionally substituted monocyclic heteroaryl, attached at a ringcarbon.
Such as monocyclic heteroaryl can be 5-membered or 6-membered monocyclic
heteroaryl.
More preferably, 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, 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, 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, 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, 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 that, in Het, any ring-carbon atom, which is directly bonded to
the ring atom (ring-carbon atom) which is the point of attachment to the -CH(R8)- moiety, 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 ringcarbon
atom at the 3-position of the ring (calculated with respect to the pyridine ring nitrogen
atom) is unsubstituted.
It is particularly preferred that, Het is an optionally substituted 6-membered monocyclic
heteroaryl, attached at a ring-carbon, and which, if substituted, is substituted by a substituent
(e.g. as defined herein) at a ring-carbon which is at the 4-position with respect to (i.e. is
diametrically opposite to) the heteroaryl ring-carbon which is the point of attachment to
the -CH(R8)- moiety. Therefore, for example, more 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 5-position of the ring (calculated with respect to the pyridine
ring nitrogen atom) is substituted by a substituent (e.g. as defined herein); even more
preferably in this embodiment, the ring-carbon atom at the 3-position of the ring (calculated
with respect to the pyridine ring nitrogen atom) is unsubstituted.
Alternatively or additionally, in a particular embodiment, Het is an optionally substituted
6-membered monocyclic heteroaryl, attached at a ring-carbon, and which, if substituted, is
substituted by a substituent (e.g. as defined herein) at a ring-carbon which is at a or the 3-
position with respect to the heteroaryl ring-carbon which is the point of attachment to
the -CH(R8)- moiety. For example, more particularly, when Het is an optionally substituted
pyridin-2-yl (optionally present as an agrochemically acceptable salt thereof), then the ringcarbon
atom at the 6-position of the ring (calculated with respect to the pyridine ring nitrogen
atom) is substituted by a substituent (e.g. as defined herein); even more particularly in this
embodiment, the ring-carbon atom at the 3-position of the ring (calculated with respect to the
pyridine ring nitrogen atom) is unsubstituted.
Preferably, R 0 is hydrogen, CrC 2alkyl (e.g. methyl) or dfluoroalkyl.
Preferably, X1 is O, NH, N(C C3alkyl) (e.g. NMe), N(C C3alkoxy) (e.g. N(OMe)),
C(H)(CrC 3alkoxy) (e.g. C(H)(OMe)), or C(Me)(C C2alkoxy) (e.g. C(Me)(OMe)). More
preferably, X1 is O or C(H)(C C3alkoxy), such as O or C(H)(OMe).
Preferably, n 1 is 3, 4 or 5, more preferably 4 or 5.
Preferably, n2 and n3 are independently 1, 2 or 3 (in particular 1 or 2) provided that n2
+ n3 is 3 or 4. More preferably, n2 and n3 are both 2.
Preferably, R and R 8 are both hydrogen, or R and R 8 are taken together and form
an -O- or -CrC 2alkylene- bridge (more preferably, R and R 8 are taken together and form
an -O- or -CrC 2alkylene- bridge); and R 2 and R 7 are independently hydrogen, CrC 3alkyl (in
particular methyl) or Ci-C 2alkoxyCi-C 2alkyl (in particular methoxymethyl); R 3 , R 4 and R 5
are independently hydrogen or CrC 3alkyl (in particular methyl), provided that two or all
(preferably all) of R 3 , R 4 and R 5 are hydrogen; and R 6 is hydrogen; CrC 3alkyl (in particular
methyl); or Ci-C 2alkoxyCi-C 2alkyl (in particular methoxymethyl).
Preferably, R 2 and R 7 are independently hydrogen, methyl or methoxymethyl.
Preferably, R 3 , R 4 and R 5 are hydrogen.
Preferably, R 6 is hydrogen.
More preferably, R and R 8 are both hydrogen, or R and R 8 are taken together and
form an -O- or -C -C2alkylene- bridge (even more preferably, R and R 8 are taken together
and form an -O- or -C -C2alkylene- bridge); and R 2 and R 7 are independently hydrogen,
methyl or methoxymethyl; and R 3 , R 4 , R 5 and R 6 are hydrogen.
Still more preferably, when R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-,
-C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-, or -CH(R )-C(R20)(R2 )-CH(R22)-, then R4 and R6
taken together are:
Preferably, when R4 and R6 taken together
are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-,
-C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-, or -CH(R )-C(R20)(R2 )-CH(R22)-,
then the compound of formula (I) is a compound of formula (IA) or (IB):
wherein G, X, R , R2, R3, R5, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined hereinbefore, and
wherein X2 is -O- or -CrC 2alkyl-.
Preferably, X2 is -0-.
Preferably, R and/or R22 are hydrogen.
Preferably, R20 and R2 taken together are oxo (=0), =N-0-R 0 , or =CH2; or R20 and
R2 , together with the carbon atom to which they are attached, form a 5, 6 or 7 (in particular 5
or 6) membered saturated heterocyclyl, wherein the heterocyclyl has two ring heteroatoms
independently being oxygen or sulfur and which are not directly bonded to each other, and
wherein the heterocyclyl is optionally substituted by 1, 2 or 3 (in particular 1 or 2) ring-carbon
substituents independently being CrC 2alkyl (e.g. methyl).
In a preferable embodiment of the invention ()e.g. wherein Q is Q1), the compound of
formula (I) is a compound described in any of Tables 1 to 46, as described and/or illustrated
herein, optionally present (e.g. where chemically possible) as an agrochemically acceptable
salt thereof.
In a more preferable embodiment of the invention, the compound of formula (I) is any
one of the compounds A8, A9 A 10, A 11, A 12, A 13, A 14, A 16, or P 1 , as described and/or
illustrated herein, optionally present (e.g. where chemically possible) as an agrochemically
acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
In an even more preferable embodiment of the invention, the compound of formula (I)
is any one of the compounds A8, A9, A10, A14 or A16, as described and/or illustrated herein,
optionally present (e.g. where chemically possible) as an agrochemically acceptable salt
(e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
In all embodiments or aspects of the invention, wherein Q is of formula Q 1, it is strongly
preferred that the compound of formula (I) is a compound of formula (IC):
wherein X, R , R2, R3, R4, R5, R6 and G are as defined herein, and wherein 40% or more (in
particular 45% or more) by molarity of the compound of formula (IC) has the indicated
stereochemistry at the ring-carbon atom bonded to R5 and R6. For example, this broadest
definition of formula (IC) includes compounds which are substantially racemic at the ringcarbon
atom bonded to R5 and R6, and also includes compounds enriched with isomer(s)
having the stereochemistry indicated at the ring-carbon atom bonded to R5 and R6.
More preferably, more than 50% (still more preferably more than 70% or more than
80%, most preferably more than 90% or more than 95%) by molarity of the compound of
formula (IC) has the indicated stereochemistry at the ring-carbon atom bonded to R5 and R6.
This more preferred definition of formula (IC) includes compounds enriched with isomer(s)
having the stereochemistry indicated at the ring-carbon atom bonded to R5 and R6.
Depending on the nature of the substituents G, R , R2, R3, R4, R5 and R6, compounds
of formula (1-1) may exist in different isomeric forms. When G is hydrogen, for example,
compounds of formula (I) may exist in different tautomeric forms, all of which are
encompassed by the present invention:
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 .
Where Q is a group of formula Q2 as defined above, a compound of formula (I) has the
general structure (1-2):
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, R ,
R34 , R35 and/or R36, independently of each other, are hydrogen, -C4alkyl (e.g. CrC 2alkyl),
C2-C4 alkynyl (in particular C 2-C3alkynyl-CH2- , e.g. ethynyl-CH2-), Ci-C 3alkoxyCi-C 3alkyl,
Ci-C 3alkylthioCi-C 3alkyl, Ci-C 3alkylsulfinylC C3alkyl, Ci-C 3alkylsulfonylC C3alkyl;
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, said heterocyclyl being 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 R33, R34 ,
R35 and R36 is alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl,
cycloalkyl or heterocyclyl;
or R33 and R34 taken together are -(CH2)n31 - or -(CH2)n32-X -(CH2)n33- and R35 and R36
are as defined herein (e.g. hereinabove), or R35 and R36 taken together
are -(CH2 ) n3i- or -(CH2 )n32- -(CH2 ) n33- and R33 and R34 are as defined herein (e.g.
hereinabove); wherein X1 is O, S, S(O), S(0) 2, NH, N(CrC 2alkyl), N(C C2alkoxy),
C(H)(CrC 2alkyl), C(C C2alkyl)2 or C(H)(C C2alkoxy); n31 is 4 or 5; and n32 and n33 are
independently 1, 2 or 3 provided that n32 + n33 is 3 or 4.
More preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2,
R33, R34 , R35 and/or R36, independently of each other, are hydrogen, CrC 4alkyl (in particular
Ci-C 2alkyl), C2-C4alkynyl (in particular C2-C3alkynyl-CH 2- , e.g. ethynyl-CH 2-),
Ci-C 3alkoxyCi-C 3alkyl (in particular Ci-C 2alkoxyCrC 2alkyl), Ci-C 3alkylthioCi-C 3alkyl (in
particular Ci-C 2alkylthioCrC 2alkyl), Ci-C 3alkylsulfinylCi-C 3alkyl (in particular
Ci-C 2alkylsulfinylCrC 2alkyl), CrC 3alkylsulfonylCi-C 3alkyl (in particular
CrC^lkylsulfonyld-C^lkyl); 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, said heterocyclyl being 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 R33, R34 , R35 and R36 is alkenyl, alkynyl, alkoxyalkyl,
alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl.
Still more preferably, R33, R34 , R35 and/or R36, independently of each other, are
hydrogen, CrC 3alkyl (in particular Ci-C 2alkyl such as methyl) or Ci-C 3alkoxyCi-C 3alkyl (in
particular C -C2alkoxyC -C2alkyl); provided that no more than one (in particular none) of R33,
R34 , R35 and R36 is alkoxyalkyl.
Even more preferably, R33, R34 , R35 and/or R36, independently of each other, are
hydrogen or C -C2alkyl (preferably hydrogen or methyl).
Most preferably (especially when Y is CR R or -CR 0R CR 2R313-), R33, R34 , R35
and R36 are hydrogen.
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, at
least one (more preferably 2, 3 or 4, still more preferably 3 or 4, most preferably all four) of
R33, R34 , R35 and R36, independently of each other, are hydrogen or C C4alkyl (e.g. H or
CrC 3alkyl, or H or Ci-C 2alkyl); and/or R34 and R35 are taken together as described herein.
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, Y is
O, S, S(O), S(0) 2, C(O), CR R or -CR 0R CR 2R313- . More preferably, Y is O, C(O),
CR R or -CR 0R CR 2R3 3- .
Even more preferably, e.g. in all aspects and/or embodiments of the invention when Q
is Q2, Y is O or CR R39 , in particular Y is O or CH2.
In one preferable embodiment, Y is CR R3 , in particular Y is CH2.
However, most preferably, e.g. in all aspects and/or embodiments of the invention
when Q is Q2, Y is O.
Preferably, e.g. in all aspects and/or embodiments of the invention, in R38 and R3 , one
or both of R38 and R39 is or are hydrogen; or R38 and R39 taken together are -(CH2 ) n 37- or
preferably -(CH2)n38-X 2-(CH2)n39- . In this embodiment, preferably Y is CR R39 and/or
preferably X32 is O.
In one particular embodiment when Q is Q2, R38 and R39 are taken together and
are -(CH2)n37- or -(CH2)n38-X 2-(CH2 ) 3 9-. In this embodiment, preferably Y is CR R39 and/or
preferably X32 is O.
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2 , X32
is O, S, S(O), S(0) 2, C(H)(C C3alkyl), C(C C2alkyl)2 or C(H)(C C3alkoxy). Most preferably,
X32 is O.
Preferably, n37 is 2, 3, 4 or 5, more preferably 4 or 5.
Preferably, n38 and n39 are independently 1, 2 or 3 provided that n38 + n39 is 2, 3 or
4. Preferably, n38 + n39 is 3 or 4. Most preferably, n38 is 2 and n39 is 2 (in which case,
preferably, X32 is O).
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, R38
and R39 are, independently of each other:
hydrogen, C1-C4alkyl (in particular d-dalkyl), C2-C3alkenyl-CH2- (in particular
ethenyl-CH2-), C2-C3alkynyl-CH2- (in particular ethynyl-CH2-), C -C2fluoroalkyl (in particular
dfluoroalkyl), d-dalkoxyd-dalkyl, d-dalkylthiod-dalkyl, d-C 3alkylsulfinyld-C 3alkyl,
or d-C 3alkylsulfonyld-C 3alkyl;
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which
independently are d-C 3alkyl (in particular methyl or ethyl) or d-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(d-C 3alkyl), N(d-C 2fluoroalkyl), N[C(0)d-C 3alkyl],
N[C(0)d-C 2fluoroalkyl] or N(d-C 2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being CrCsalkoxy (in particular
CrC 2alkoxy) and optionally further substituted by one substituent being CrC 2alkyl (in
particular methyl);
C 3-C6cycloalkylCi-C 2alkyl- (in particular C3-C6cycloalkylmethyl-) or C3-C6cycloalkyld-
C2alkyl- (in particular 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-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(CrC 2alkyl), N(d-
C2fluoroalkyl), N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety;
C3-C6cycloalkylCrC 2alkyl- (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
HetA or HetA-CH2- , wherein HetA 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 -C3alkyl (e.g. d-C 2alkyl), d-C 2fluoroalkyl, CrC 3alkyl-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), d-C 3alkoxy (e.g. d-C 2alkoxy), d -
C2fluoroalkoxy, halogen (e.g. fluorine or chlorine), cyano or nitro; 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 2fluoroalkyl, d-C 3alkyl-C(0)-,
d-C 2fluoroalkyl-C(0)- or d-C 2alkyl-S(0) 2- substituent;
provided that no more than one of R38 and R3 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(d-C 3alkyl), N(d-C 2fluoroalkyl),
N[C(0)d-C 3alkyl], N[C(0)d-C 2fluoroalkyl] or N(Cr 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(Cr C3alkyl), N(Cr C2fluoroalkyl), N[C(0)C r C3alkyl],
N[C(0)Ci-C 2fluoroalkyl] or N(Cr C2alkoxy) moiety; or HetA or HetA-CH2- ;
or R38 is hydrogen or Ci-C 2alkyl (in particular H or Me), and R3 is CrC 2alkoxy (in
particular methoxy);
or R38 and R39 taken together are -(CH2)n37- or -(CH2)n38-X 2-(CH2)n39- .
In the above preferred embodiment, preferably Y is CR R39 and/or preferably X32 is O.
More preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2:
R38 is hydrogen or CrC 2alkyl (preferably H or Me, more preferably hydrogen); and
R39 is:
CrC 2alkoxy (in particular methoxy);
C2-C3alkynyl-CH 2- (in particular ethynyl-CH 2-);
Ci-C 3alkoxyCi-C 3alkyl;
Ci-C 3alkylthioCi-C 3alkyl (preferably Ci-C 2alkylthio-CH 2CH2- or more preferably
CrC 2alkylthio-CH(Me)CH 2-);
Ci-C 3alkylsulfinylC C3alkyl;
d-dalkylsulfonyld-dalkyl;
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(C C3alkyl), N(C C2fluoroalkyl), N[C(0)C C3alkyl],
N[C(0)C 1-C2fluoroalkyl] or N( -C2alkoxy) moiety (or more preferably is replaced by an
oxygen or sulfur atom or by a S(O), S(0) 2, NH, N( -C3alkyl) or N( -C2alkoxy) moiety; or
still more preferably is replaced by an oxygen or sulfur atom);
d-dcycloalkyl substituted by one substituent being d-dalkoxy (in particular
d-C 2alkoxy) and optionally further substituted by one substituent being d-C 2alkyl (in
particular methyl);
C3-C6cycloalkylmethyl- or C3-C6cycloalkylmethyl- substituted by one or two ring
substituents which independently are d-C 3alkyl (in particular d-C 2alkyl) or d-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(d-dalkyl), N(ddfluoroalkyl),
N[C(0)d-C 3alkyl], N[C(0)d-dfluoroalkyl] or N(d-dalkoxy) moiety (or more
preferably is replaced by an oxygen or sulfur atom or by a N[C(0)d-C 3alkyl] or
N[C(0)d-C 2fluoroalkyl] moiety);
d-dcycloalkylmethyl- substituted by one ring substituent being d-dalkoxy (in
particular d-dalkoxy) and optionally further substituted by one ring substituent being
Crdalkyl (in particular methyl); or
HetA or HetA-CH2- , wherein Het A 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 d-dalkyl (in particular d-dalkyl), d-dfluoroalkyl (in particular
dfluoroalkyl), d-Csalkyl-C^O)-, C1-C2fluoroalkyl-C(0)- hydroxy (including any oxo
tautomer), C2-C3alkenyl (in particular ethenyl or prop-1-enyl), C2-C3alkynyl (in particular
ethynyl or prop-1-ynyl), CrC 3alkoxy (in particular CrC 2alkoxy), Ci-C 2fluoroalkoxy (in
particular Cifluoroalkoxy), halogen (in particular fluorine or chlorine), cyano or nitro; 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 CrC 3alkyl, CrC 2fluoroalkyl, Ci-C 3alkyl-C(0)-,
Ci-C 2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent;
or R38 and R39 taken together are -(CH2)n37- or -(CH2)n38-X 2-(CH2)n39- .
In the above preferred embodiment, preferably Y is CR R3 and/or preferably X32 is O.
Even more preferably, e.g. in all aspects and/or embodiments of the invention when Q
is Q2:
R38 is hydrogen or C -C2alkyl (preferably H or Me, more preferably hydrogen); and
R39 is:
d-dalkylthiod-dalkyl (preferably C -C2alkylthio-CH 2CH2- or more preferably
C C2alkylthio-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 -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);
HetA or HetA-CH2- , wherein Het A 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 Ci-C 3alkyl (in particular Ci-C 2alkyl), Ci-C 2fluoroalkyl (in particular
Cifluoroalkyl), Ci-C 3alkyl-C(0)-, CrC 2fluoroalkyl-C(0)-, 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 CrC 2alkoxy), CrC 2fluoroalkoxy (in
particular Cifluoroalkoxy), halogen (in particular fluorine or chlorine), cyano or nitro; 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 CrC 3alkyl, CrC 2fluoroalkyl, Ci-C 3alkyl-C(0)-,
Ci-C 2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent;
or R38 and R39 taken together are -(CH2)n37- or -(CH2)n38-X 2-(CH2)n39- .
In the above even more preferred embodiment, preferably Y is CR R3 and/or
preferably X32 is O.
In one particularly preferable embodiment (which e.g. can apply to all aspects and/or
embodiments of the invention when Q is Q2), R38 and R3 , independently of each other, are
hydrogen or C -C3alkyl (preferably hydrogen or C -C2alkyl, more preferably hydrogen or
methyl, most preferably hydrogen). In this embodiment, preferably, Y is CR R39.
In another preferable embodiment (which e.g. can apply to all aspects and/or
embodiments of the invention), R38 is hydrogen, and R39 is Ci-C 3alkylthioCrC 3alkyl. In this
embodiment, R39 preferably is CrC 2alkylthio-CH 2CH2- or more preferably is
C1-C2alkylthio-CH(Me)CH 2- . In this embodiment, preferably, Y is CR R39.
In another preferable embodiment (which e.g. can apply to all aspects and/or
embodiments of the invention when Q is Q2), R38 is hydrogen and R39 is
C4-C6cycloalkylmethyl- or C4-C6cycloalkylmethyl- substituted by one or two ring substituents
which independently are C -C3alkyl (in particular C -C2alkyl) or C -C2fluoroalkyl, 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 -C3alkyl]
or N[C(0)Ci-C 2fluoroalkyl] moiety). In this embodiment, preferably, Y is CR R39.
Within the above preferable embodiment, then preferably R38 is hydrogen and R39 is
heterocyclyl-methyl-, wherein the heterocyclyl is V, wherein V is one of the following subformulae
V , V2, V3, V4, V5, V6, V7, V33, V34 , V37, V38, V4 1, V42, V43, V44, V47, V87, V89, V90 or V107
wherein: A is the position of attachment to the -methyl- moiety; and R is hydrogen,
C C2alkyl (e.g. methyl), C C2fluoroalkyl (e.g. Cifluoroalkyl), -C(0)C C3alkyl (e.g. -C(O)-
methyl), -C(0)C C2fluoroalkyl (e.g. -C(O)dfluoroalkyl) or C C2alkoxy.
More preferably, V is one of the sub-formulae \ , V2, V4, V6, V7, V33, V34 , V4 , V42, V43,
V44, V87, V89 or V90. Even more preferably, V is one of the sub-formulae V2, V6, V7, V33, V34 ,
V4 1, V42, V43, V44, V87, V89 or V90.
Yet more preferably, V is one of the sub-formulae V2, V7, V87 or V90. Further more
preferably, V is one of the sub-formulae V2, V7 or V90.
Most preferably, V is sub-formula V7.
Preferably, R is -C(0)C C3alkyl (e.g. -C(O)methyl) or -C(0)C C2fluoroalkyl
(e.g. -C(O)dfluoroalkyl).

CLAIMS
1. A compound of formula (I):
wherein:
X is methyl or chlorine;
R is fluorine or bromine;
R2 is ethynyl, C-i-C3alkoxy-, C-i-C3haloalkoxy-, or C-i-Csalkoxy-C-pCsalkoxy-; and
Q is a group of either formula Q 1
wherein:
R3, R4 and R5, independently of each other, are hydrogen, Ci-C 5alkyl, C2-C4 alkenyl,
C2-C4alkynyl, C1-C2fluoroalkyl or d-CsalkoxyCrCsalkyl;
R6 is hydrogen, C C5alkyl, C2-C4alkenyl, C2-C4alkynyl, R6 -CºC-CH2- , C
C2fluoroalkyl, C-i-CsalkoxyC-i-Csalkyl, C-i-CsalkylthioC-i-Csalkyl, C-i-CsalkylsulfinylCr
C3alkyl, d-Csalkyl-sulfonyld-Csalkyl, 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,
or R6 is T-(CH2)m-CH(R7)-, wherein m is 0 or 1 and either R7 is hydrogen or R7 and R5
together are a bond, and T is an optionally substituted heterocyclyl as defined below;
or R6 is Het-CH(R8)-, wherein either R8 is hydrogen or R8 and R5 together are a bond,
and Het is an optionally substituted heteroaryl as defined below;
or R6 is C 3-C6cycloalkylCi-C 2alkyl-; or is C4-C6cycloalkylCi-C 2alkyl-, substituted at a
cycloalkyl ring-carbon atom which is not the ring-carbon atom attached to the -C
C2alkyl- moiety and which is not bonded directly to the ring-carbon atom attached to
the -Ci-C 2alkyl- moiety, by one or two ring substituents which independently are: =NO-
R 0 , oxo (=0), C C4alkoxy, C C2haloalkoxy, 2-(C C3alkoxy)-ethoxy,
C3-C5cycloalkyloxy, (C3-C5cycloalkyl)methoxy, C2-C3alkenyl-CH 2-oxy, CrC 3alkyl or
C -C2fluoroalkyl; or benzyloxy in which the phenyl ring is optionally substituted by one
or two substituents independently being CrCsalkyl, CrC 2fluoroalkyl, CrC 3alkyl-C(0)-,
C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E,
-S(0) 2-R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) ,
C2-C3alkynyl, -CºC-R6 , CrC 3alkoxy, CrC 2fluoroalkoxy, cyclopropyloxy,
CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro ;
or R6 is benzyl optionally substituted on its phenyl ring by one or two substituents which
independently are: CrCsalkyl, CrC 2fluoroalkyl, CrC 3alkyl-C(0)-,
CrC 2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E,
-S(0) 2-R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) ,
C2-C3alkynyl, -CºC-R6 , CrC 3alkoxy, CrC 2fluoroalkoxy, cyclopropyloxy,
CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro;or R3 and R4 taken together
are -(CH2) - or -(CH2) 2-X -(CH2) 3- and R5 and R6 are as defined above,
or R5 and R6 taken together are -(CH2) 1- or -(CH2) 2-X -(CH2) 3- and R3 and R4 are as
defined above
or R4 and R6 taken together are
-C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-, -C(R )(R 2)-C(R )=C(R15)-
C(R 7)(R18)-, or -CH(R )-C(R20)(R2 )-CH(R22)-; and
T is a 4 to 7 membered monocyclic- or an 8 to 11 membered fused bicyclicheterocyclyl,
having one or two ring heteroatoms independently selected from oxygen,
sulfur and nitrogen; and wherein T is optionally substituted by 1 or 2 ring-carbon
substituents independently being C C3alkyl, -C2fluoroalkyl, -SC C3alkyl, -S(0)C
C3alkyl, -S(0) 2Ci-C3alkyl, or oxo (=0), and/or is optionally substituted by one
CrC 4alkyl, CrC 2fluoroalkyl, Ci-C 4alkoxy, Ci-C 2fluoroalkoxy; or a R -C(0)-, or a
CrC 2alkyl-S(0) 2- 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;
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,
C C3alkyl-C(0)-, C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E,
-S(0) 2-R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) ,
C2-C3alkynyl, -CºC-R6 , d-dalkoxy, d-dfluoroalkoxy, cyclopropyloxy,
CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro; 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-i-C2fluoroalkyl,
Ci-C 3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or C C2alkyl-S(0) 2- substituent;
wherein:
R6 is C-ifluoroalkyl, fluorine, chlorine or bromine;
R6B, R6C and R6CC independently are hydrogen, methyl, dfluoroalkyl, fluorine or
chlorine; provided that R6B, R6C and R6CC in total contain no more than one carbon
atom, and R6B, R6C and R6CC in total comprise no more than one chlorine;
R6BB , R6C and R6C2 independently are hydrogen, methyl, dfluoroalkyl, fluorine or
chlorine; provided that R6BB , R6C and R6C2 in total contain no more than one carbon
atom, and R6BB , R6C and R6C2 in total comprise no more than one chlorine; and
provided that -C(R6BB)=C(R6C )(R6C2) is not d-dalkenyl;
R6D and R6E independently are d-dalkyl, dfluoroalkyl, or -N(R6 )(R6 ) ;
R6 is -C(0)-Ci-dalkyl, -C(0)-dfluoroalkyl, -S(0) 2-d-dalkyl, -S(0) 2-Cifluoroalkyl,
d-dalkyl, or dfluoroalkyl;
R6G and R6 independently are hydrogen, methyl or dfluoroalkyl; and
R6 is hydrogen, d-dalkyl, or dfluoroalkyl; and
R is C -C4alkyl, C2-C4alkenyl attached at a carbon atom partaking in the C=C double
bond, Ci-C 2fluoroalkyl, Ci-C2alkoxymethyl-, CrC 3alkoxy, cyclopropyl, furanyl,
morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, pyrazol-5-yl, 3-methylpyrazol-5-yl,
1-methylpyrazol-5-yl, 1,3-dimethylpyrazol-5-yl; or phenyl or phenyl substituted by 1 or 2
substituents independently being methyl, ethyl, dfluoroalkyl, methoxy, C-ifluoroalkoxy,
fluorine, chlorine, SC C3alkyl, S(0)C C3alkyl, or S(0) 2CrC 3alkyl;
R 0 is hydrogen, Ci-C4alkyl, Ci-C2fluoroalkyl, 2-(Ci-C 3alkoxy)-ethyl, C3-C5cycloalkyl or
(C3-C5cycloalkyl)methyl;
X1 is O, S, S(O), S(0) 2, NH, N(C C3alkyl), N(C C3alkoxy), C(H)(C C2alkyl),
C(C C2alkyl)2, C(H)(C C3alkoxy) or C(Me)(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;
R and R 8 are both hydrogen, or R and R 8 are taken together and form
an -O- or -Ci-C 2alkylene- bridge; and
R 2 and R 7 are independently hydrogen, C -C3alkyl or C -C2alkoxyC -C2alkyl;
R 3 , R 4 and R 5 are independently hydrogen, C -C3alkyl or C -C2alkoxyC -C2alkyl,
provided that one, two or all of R 3 , R 4 and R 5 are hydrogen;
R 6 is hydrogen; -C3alkyl; d-dalkoxyCrdalkyl; phenyl optionally substituted by 1,
2 or 3 of, independently, C C3alkyl, C C2fluoroalkyl, C C3alkyl-C(0)-,
C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E,
-S(0) 2-R6E, -N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) ,
C2-C3alkynyl, -CºC-R6 , Ci-C 3alkoxy, Ci-C2fluoroalkoxy, cyclopropyloxy,
CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro; or a 5-membered or 6-
membered heteroaryl, attached at a ring-carbon and optionally substituted by 1, 2 or 3
ring-carbon substituents independently being Ci-C3alkyl, CrC 2fluoroalkyl,
CrC 3alkyl-C(0)-, C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, S(0) 2R6E,
-S(0) 2-R , -N(R )(R ) , hydroxy, C2-C3alkenyl, -C(R )=C(R )(R ) ,
C2-C3alkynyl, -CºC-R6 , CrC 3alkoxy, CrC 2fluoroalkoxy, cyclopropyloxy,
CH2=CH-CH2-0-, HCºC-CH2-0-, halogen, cyano or nitro;
R and R22 are independently hydrogen, -C3alkyl or Ci-C 2alkoxyCrC 2alkyl;
and R20 and R2 are independently hydrogen, Ci-C 3alkyl or Ci-C 2alkoxyCrC 2alkyl;
or R20 and R2 taken together are oxo (=0), =N-0-R 0 , or =CH2;
or R20 and R2 , together with the carbon atom to which they are attached, form a 5, 6 or
7 membered saturated heterocyclyl, wherein the heterocyclyl has two ring heteroatoms
independently being oxygen or sulfur and which are not directly bonded to each other,
and wherein the heterocyclyl is optionally substituted by 1, 2 or 3 ring-carbon
substituents independently being Ci-C 2alkyl;
and wherein in Q2:
R33, R34 , R35 and R36, independently of each other, are hydrogen, C C5alkyl, C2-
C4alkenyl, C2-C4alkynyl, Ci-C 2fluoroalkyl, CrCsalkoxyCrCsalkyl, d-CsalkylthioCr
C3alkyl, Ci-C 3alkylsulfinylCi-C 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, said heterocyclyl
being attached at a ring carbon atom within the heterocyclyl ;
provided that no more than one of R33, R34 , R35 and R36 is alkenyl, alkynyl, alkoxyalkyl,
alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
or R33 and R34 taken together are -(CH2)n31 - or -(CH2)n32-X -(CH2)n33- and R35 and R36
are as defined above, or R35 and R36 taken together
are -(CH2)n31 - or -(CH2)n32-X -(CH2)n33- and R33 and R34 are as defined above;
X3 1 is O, S, S(O), S(0) 2, NH, N(C C2alkyl), N(C C2alkoxy), C(H)(C C2alkyl),
C(Ci-C 2alkyl)2 or C(H)(C C2alkoxy);
n31 is 2, 3, 4 or 5;
n32 and n33 are independently 1, 2 or 3 provided that n32 + n33 is 2, 3 or 4;
or R34 and R35 taken together are -C(R 7 )=C(R 7 )-;
wherein R 7 and R 7 independently are hydrogen or Ci-C 2alkyl; and
Y is O, S, S(O), S(0) 2, N(Ci-C 2alkyl), N(Ci-C 2alkoxy), C(O), CR R or -
C R 310 R 3 11C R 312 R 313_.
R38 and R3 are, independently of each other: hydrogen, CrC 6alkyl, C2-C4alkenyl, C2-
C4alkynyl, Ci-C 2fluoroalkyl, Ci-C 3alkoxyCi-C 3alkyl, Ci-C 3alkylthioCi-C 3alkyl, d -
C3alkylsulfinylCrC 3alkyl, or Ci-C 3alkylsulfonylCrC 3alkyl; C3-C6cycloalkyl or C3-
C6cycloalkyl substituted by one or two substituents which independently are CrC 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(Ci-C 3alkyl), N(d-
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 and optionally further
substituted by one substituent being -C2alkyl; C5-C6cycloalkenyl or C5-C6cycloalkenyl
substituted by one or two d-dalkyl substituents; d-C 6cycloalkyld-dalkyl- or C3-
C6cycloalkyld-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-dalkyl), N(Ci-C 2fluoroalkyl), N[C(0)d-dalkyl],
N[C(0)CrC 2fluoroalkyl] or N(C C2alkoxy) moiety; C3-C6cycloalkylCidalkyl-
substituted by one ring substituent being d-C 3alkoxy and optionally further
substituted by one ring substituent being d-C 2alkyl; or HetA or HetA-CH 2- ;
wherein HetA 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-C 2fluoroalkyl,
d-dalkyl-C(O)-, C C2fluoroalkyl-C(0)-, -C(0)-N(R 6 )(R6 ) , SR6E, S(0)R 6E, -S(0) 2-R6E,
-N(R6 )(R6G) , hydroxy, C2-C3alkenyl, -C(R6BB)=C(R6C )(R6C2) , C2-dalkynyl, -CºC-R6 ,
d-dalkoxy, Ci-C 2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH 2-0-, HCºC-CH2-0-,
halogen, cyano or nitro; 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, C C2fluoroalkyl, d-C 3alkyl-C(0)-, C C2fluoroalkyl-C(0)- or
d-C 2alkyl-S(0) 2- substituent;
provided that no more than one of R38 and R3 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(Ci-C 3alkyl), N(Ci-C 2fluoroalkyl),
N[C(0)CrC 3alkyl], 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(CrC 3alkyl), N(C C2fluoroalkyl),
N[C(0)CrC 3alkyl], N[C(0)C C2fluoroalkyl] or N(C C2alkoxy) moiety, or HetA or
HetA-CH2- ;
or R is hydrogen or C C2alkyl, and R is C C2alkoxy;
or R and R39 taken together are -(CH2)n37- or -(CH2)n38-X -(CH2)n39- ;
wherein X32 is O, S, S(O), S(0) 2, NH, N(C C3alkyl), N(C C2fluoroalkyl),
N[C(0)C C3alkyl], N[C(0)C C2fluoroalkyl], N(C C2alkoxy), C(H)(C C3alkyl),
C(C C2alkyl)2 or C(H)(C C3alkoxy);
n37 is 2, 3, 4, 5 or 6; and
n38 and n39 are independently 0, 1, 2 or 3 provided that n38 + n39 is 2, 3, 4 or 5; and
R3 0 , R3 , R3 2 and R3 3 are independently of each other hydrogen or C C4alkyl
provided that no more than one of R3 0, R3 ,R3 2 and R3 3 is C3-C4alkyl;
and wherein R6 , R6BB , R6C , R6C2, R6E, R6 , R6G, R6 and R6 are as defined
hereinabove for when Q is Q 1; 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(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-C 2alkyl, Cifluoroalkyl, 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, C1-C2alkyl, dfluoroalkyl, C
C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro); or
C -C6alkoxy-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(CrC 2alkyl)-;
Xa, X , X , X , Xe and X are independently of each other oxygen or sulfur;
Ra is H, C -C2ialkyl, C2-C2ialkenyl, C2-Ci8alkynyl, C -Ciofluoroalkyl, C -Ciocyanoalkyl,
Ci-Ci0nitroalkyl, Ci-Ci0aminoalkyl, C -C5alkylamino(Ci -C5)alkyl, C2-C8dialkylamino(Cr
C5)alkyl, C3-C7cycloalkyl(C1-C5)alkyl, C1-C5alkoxy(C1-C5)alkyl, d-dalkenyloxy(d-
C5)alkyl, C3-C5alkynyloxy(C1-C5)alkyl, C1-C5alkylthio(C1-C5)alkyl, d-dalkylsulfinyl(d-
C5)alkyl, C1-C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C
dalkylcarbonyl(d-d)alkyl, C1-dalkoxycarbonyl(C 1-d)alkyl, aminocarbonyl(dd)
alkyl, C1-dalkylaminocarbonyl(C 1-d)alkyl, C2-C8dialkylaminocarbonyl(d-C 5)alkyl,
C -dalkylcarbonylamino(C -d)alkyl, /V-(C -d)alkylcarbonyl-/V-(C -d)alkylamino(C -
d)alkyl, d-dtrialkylsilyl(d-d)alkyl, phenyl(C -d)alkyl (wherein the phenyl 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), heteroaryl(C -d)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, d-dcycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of,
independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen,
cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen , cyano or nitro;
R is d-d 8alkyl, C3-d 8alkenyl, C3-d 8alkynyl, C2-d 0fluoroalkyl, d-d 0cyanoalkyl, d -
donitroalkyl, d -Ci0aminoalkyl, d-dalkylamino (Ci -d)alkyl, d-ddialkylamino(dd)
alkyl, d-dcycloalkyl(d-d)alkyl, C -dalkoxy(d-d)alkyl, d-dalkenyloxy(C
d)alkyl, d-dalkynyloxy(d-d)alkyl, C -dalkylthio(d-d)alkyl, d-dalkylsulfinyl(dd)
alkyl, C -dalkylsulfonyl(d-C 5)alkyl, d-dalkylideneaminoxy(d-d)alkyl, d -
dalkylcarbonyl(d-d)alkyl, C -dalkoxycarbonyl(d-d)alkyl, aminocarbonyl(Cid)
alkyl, C -dalkylaminocarbonyl(d-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl,
C -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, Ci-
Csalkoxy, CrC 3fluoroalkoxy, CrC 3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl,
halogen, cyano, or nitro), heteroarylCi-C 5alkyl (wherein the heteroaryl is optionally
substituted by 1, 2 or 3 of, independently, Ci-C 3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, d -
C3fluoroalkoxy, Ci-C 3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or
nitro), C3-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of,
independently, Ci-C 3alkyl, CrC 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen,
cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, CrCsfluoroalkoxy, halogen, cyano or nitro; and
R and R are each independently of each other hydrogen, d-C 0alkyl, C3-C 0alkenyl,
C3-C10alkynyl, C2-C10fluoroalkyl, d-C 10cyanoalkyl, d-C 10nitroalkyl, d-C 10aminoalkyl,
C1-C5alkylamino(C 1-C5)alkyl, C2-C8dialkylamino(C 1-C5)alkyl, C3-C7cycloalkyl(d-
C5)alkyl, C1-C5alkoxy(C1-C5)alkyl, C 3-C5alkenyloxy (d-C5)alkyl, C3-C5alkynyloxy(d-
C5)alkyl, CrdalkylthiotCrd^lkyl, C1-C5alkylsulfinyl(C 1-C5)alkyl, CrC 5alkylsulfonyl(Cr
C5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, Ci-C5alkylcarbonyl(Ci-C 5)alkyl, d -
C5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(d-C 5)alkyl, d-C 5alkylaminocarbonyl(Ci-
C5)alkyl, C2-C 8dialkylaminocarbonyl (d-C5)alkyl, C1-C5alkylcarbonylamino(C 1-C5)alkyl,
/V-(C1-C5 )alkylcarbonyl-/V-(C2-C5)alkylaminoalkyl, Cs-CetrialkylsilyKd-CsJalkyl,
phenyl(C -C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of,
independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, CrCsfluoroalkoxy, Ci-
Csalkylthio, d-dalkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or nitro),
heteroaryl(CrC 5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of,
independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, Ci-
Csalkylthio, Ci-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, Ci-C3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen,
cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, d -
dalkyl, Ci-C 3fluoroalkyl, d-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro;
heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, d -
C3alkyl, Ci-C 3fluoroalkyl, Ci-C 3alkoxy, Ci-C 3fluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro;
phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, CrC 3alkyl, d -
C3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, 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, 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, C2-C8dialkylamino(Cid)
alkyl, C3-C7cycloalkyl(CrC 5)alkyl, d-dalkoxy(d-d)alkyl, C3-C5alkenyloxy(Cid)
alkyl, d-dalkynyloxy(d-d)alkyl, C1-dalkylthio(C 1-d)alkyl, d-dalkylsulfinyKdd)
alkyl, C1-dalkylsulfonyl(C 1-C5)alkyl, d-dalkylideneaminoxy(C 1-d)alkyl, d -
dalkylcarbonyl(d-d)alkyl, C1-dalkoxycarbonyl(C 1-d)alkyl, aminocarbonyl(dd)
alkyl, C1-dalkylaminocarbonyl(C 1-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl,
d-dalkylcarbonylamino(Ci-d)alkyl, /V-(d-C 5)alkylcarbonyl-/V-(d-C 5)alkylamino(dd)
alkyl, C3-C6trialkylsilyl(CrC 5)alkyl, phenyl(d-d)alkyl (wherein the phenyl is
optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d -
dalkoxy, Crdfluoroalkoxy, d-dalkylthio, Crdalkylsulfinyl, d-dalkylsulfonyl,
halogen, cyano, or nitro), heteroaryl(C -d)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 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 -
dalkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, halogen, cyano or nitro;
heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, d -
dalkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, halogen, cyano or nitro;
phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
dfluoroalkyl, Ci-C3alkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; diphenylamino
or diphenylamino substituted by 1, 2 or 3 of, independently, C -C3alkyl, C
C3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; or C3-
C7cycloalkylamino, di(C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, CrCi 0alkoxy, d -
Ciofluoroalkoxy, C -C5alkylamino or di(CrC 4alkyl)amino;
R and R9 are independently of each other Ci-Ci 0alkyl, C2-Ci 0alkenyl, C2-Ci 0alkynyl, d -
C 0alkoxy, Ci-Ci 0fluoroalkyl, C -Ciocyanoalkyl, Ci-Ci 0nitroalkyl, Ci-Ci 0aminoalkyl, d -
C5alkylamino(Ci-C 5)alkyl, C 2-C8dialkylamino(Ci-C 5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl,
C -C5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(Ci-C 5)alkyl, C3-C5alkynyloxy(Ci-C 5)alkyl, C
C5alkylthio(Ci-C 5)alkyl, C1-C5alkylsulfinyl(C -C5)alkyl, C -C5alkylsulfonyl(Ci-C 5)alkyl, C2-
C8alkylideneaminoxy(C1-C5)alkyl, C1-C5alkylcarbonyl(C1-C5)alkyl, d -
dalkoxycarbonyl(C -d)alkyl, aminocarbonyl(C -d)alkyl, d-dalkylaminocarbonyl(dd)
alkyl, d-C 8dialkylaminocarbonyl(d-d)alkyl, C1-dalkylcarbonylamino(C 1-d)alkyl,
/V-(d-d)alkylcarbonyl-/V-(d-d)alkylaminoalkyl, d-C 6trialkylsilyl(d-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, d-dfluoroalkoxy, d -
C3alkylthio, d-dalkylsulfinyl, 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-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, d -
dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or nitro), C2-
dfluoroalkenyl, 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 -
C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;
heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;
diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, d -
C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;
phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
dfluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; diphenylamino
or diphenylamino substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d -
C3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; or C3-
dcycloalkylamino, di(C3-C7cycloalkyl)amino, d-dcycloalkoxy, C -Ciofluoroalkoxy, d -
dalkylamino or di(d-C 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 -
C3alkyl, -C3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; and
Rh is Ci-Ci 0alkyl, C3-Ci 0alkenyl, C3-Ci 0alkynyl, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d -
C 0nitroalkyl, C2-Ci 0aminoalkyl, Ci-C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino(Ci-
C5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl, Ci-C5alkoxy(Ci-C 5)alkyl, C3-C5alkenyloxy(C
C5)alkyl, C3-C5alkynyloxy(Ci-C 5)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, Ci-C5alkylsulfinyl(C
C5)alkyl, Ci-C 5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, d -
C5alkylcarbonyl(Ci-C 5)alkyl, Ci-C 5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(Ci-
C5)alkyl, Ci-C 5alkylaminocarbonyl(Ci-C 5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl,
C -C5alkylcarbonylamino(C -C5)alkyl, /V-(C -C5)alkylcarbonyl-/V-(C -C5)alkylamino(C -
C5)alkyl, 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, d-dalkylthio, Crdalkylsulfinyl, d-dalkylsulfonyl,
halogen, cyano or nitro), heteroaryl(C -d)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-dalkylsulfonyl, halogen, cyano or
nitro), phenoxy(CrC 5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of,
independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Ci-C 3fluoroalkoxy, d -
C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano or nitro),
heteroaryloxy(Crd)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3
of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, Ci-
Csalkylthio, Crdalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano or nitro), C3-
dfluoroalkenyl, 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 -
dalkyl, d-C 3fluoroalkyl, 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, Cifluoroalkyl, d-dalkoxy, Cifluoroalkoxy, fluorine,
chlorine, bromine, cyano or nitro;
and 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 as an agrochemically
acceptable salt thereof.
2. A compound according to claim 1 wherein X is methyl.
3. A compound according to claim 1 or claim 2 wherein R is fluorine.
4. A compound according to claim 1, 2 or 3, wherein R2 is -0-R 2 , and wherein R2 is
methyl, ethyl, trifluoromethyl or difluoromethyl.
5. A compound according to claim 1, 2 or 3, wherein R2 is -0-R 2 , and wherein R2 is
methyl.
6. A compound according to any one of claims 1 to 8, 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 .
7. A compound according to any one of the preceding claims, wherein R3, R4 and R5 are
hydrogen; or,
R3 and R5 are hydrogen, and R4 and R6 taken together are
-C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)- or
-C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-.
8. A compound according to any one of the preceding claims, wherein
R6 is: hydrogen, C C4alkyl, C2-C3alkynyl-CH2- , Ci-C 2alkoxyCi-C 2alkyl;
T-CH(R7)- wherein R7 is hydrogen; or Het-CH(R8)- wherein R8 is hydrogen;
or R4 and R6 taken together are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)- or
-C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-;
and wherein:
R and R 8 are taken together and form an -O- or -C -C2alkylene- bridge;
R 2 and R 7 are independently hydrogen, -C3alkyl or Ci-C 2alkoxyCrC 2alkyl;
R 3 , R 4 and R 5 are independently hydrogen or CrC 3alkyl, provided that two or all of
R 3 , R 4 and R 5 are hydrogen; and
R 6 is hydrogen; C C3alkyl; or Ci-C 2alkoxyC C2alkyl.
9. A compound according to any one of the preceding claims, wherein:
R6 is hydrogen, -C4alkyl or C 2-C3alkynyl-CH 2- .
10. A compound according to any one of claims 1 to 9, wherein:
T is a 4, 5 or 6 membered monocyclic heterocyclyl, having one ring heteroatom
independently selected from oxygen, sulfur and nitrogen;
and wherein the heterocyclyl T is optionally substituted by one R -C(0)- or
CrC 2alkyl-S(0)2- substituent on a ring nitrogen if present, or is optionally substituted by
one or two oxo (=0) substituents on a ring sulfur if present;
and wherein T is attached at a ring carbon atom to
the -(CH2)m-CH(R7)- or -CH(R7)- moiety; and
in T, the one ring heteroatom is not directly bonded to the ring atom which is the
position of attachment to the -(CH2)m-CH(R7)- or -CH(R7)- moiety; and
R is C -C3alkyl, C -C2fluoroalkyl, methoxymethyl-, or cyclopropyl.
11. A compound according to any one of claims 1 to 10, wherein:
Het is a heteroaryl, attached at a ring-carbon, which is optionally substituted by 1 or 2
ring-carbon substituents independently being C -C2alkyl, C -C2alkoxy, CifluoroalkyI, C
C2fluoroalkoxy, C C2alkyl-C(0)-, Cifluoroalkyl-CtO)-, SC C2alkyl, ethynyl, prop-1-ynyl,
fluorine, chlorine 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
ring-nitrogen atom not partaking in the C=N ring double bond by one C -C2alkyl,
CifluoroalkyI, methyl-C(O)- or dfluoroalkyl-CiO)- substituent.
12. A compound according to any one of claims 1 to 11,
wherein Het is an optionally substituted monocyclic heteroaryl, attached at a ringcarbon,
selected from: pyridinyl, pyrazolyl, imidazolyl, pyrazinyl, pyrimidinyl, and
pyridazinyl; optionally present as an agrochemically acceptable salt thereof;
and wherein, in Het, any ring-carbon atom, which is directly bonded to the ring atom
which is the point of attachment to the -CH(R8)- moiety, is unsubstituted.
13. A compound according to any one of claims 1 to 12, wherein,
when R4 and R6 taken together are -C(R )(R 2)-C(R )(R 4)-C(R )(R 6)-C(R 7)(R18)-,
-C(R )(R 2)-C(R )=C(R )-C(R 7)(R18)-, or -CH(R )-C(R20)(R2 )-CH(R22)-,
then R4 and R6 taken together are:
14. A compound according to any one of claims 1 to 13, wherein R , R , R and R
independently of each other, are hydrogen, CrCsalkyl or C -C2alkoxyC -C2alkyl;
provided that no more than one of R33, R34 , R35 and R 6 is alkoxyalkyl.
15. A compound according to any one of claims 1 to 14, wherein:
R38 and R3 , independently of each other, are hydrogen or CrCsalkyl; or
R38 is hydrogen or CrC 2alkyl; and
R39 is:
CrC 2alkoxy;
C2-C3alkynyl-CH 2- ;
Ci-C 3alkoxyCi-C3alkyl;
d-Csalkylthiod-Csalkyl;
d-CsalkylsulfinylCrCsalkyl;
d-CsalkylsulfonylCrCsalkyl;
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(Cr C2fluoroalkyl), N[C(0)CrC 3alkyl], N[C(0)C C2fluoroalkyl] or
N(Ci -C2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being C -C3alkoxy and optionally further
substituted by one substituent being C -C2alkyl;
C3-C6cycloalkylmethyl- or 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-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 Ci -C3alkoxy and
optionally further substituted by one ring substituent being C -C2alkyl; or
HetA or HetA-CH2- ,
wherein HetA is a heteroaryl, attached at a ring-carbon , which is optionally substituted
by 1, 2 or 3 ring-carbon substituents independently being CrCsalkyl, C -C2fluoroalkyl,
CrC 3alkyl-C(0)-, CrC 2fluoroalkyl-C(0)-, hydroxy (including any oxo tautomer), C2-
C3alkenyl, C2-C3alkynyl, C -C3alkoxy, C -C2fluoroalkoxy, halogen , cyano or nitro;
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,
C -C2fluoroalkyl, C -C3alkyl-C(0)-, Cr C2fluoroalkyl-C(0)- or
CrC 2alkyl-S(0) 2- substituent.
A compound according to any one of claims 1 to 15, wherein Y is O or CR R
17. A compound according to any one of claims 1 to 16, wherein :
R is fluorine,
X is methyl,
R2 is OR2 , wherein R2 is selected from methyl, ethyl and difluoromethyl, and
either Q is Q 1, wherein R3, R4, and R5 are hydrogen, and R6 is hydrogen or propargyl,
and G is hydrogen,
or Q is Q2, wherein Y is CR R3 , and R38 and R3 are each independently hydrogen or
methyl, and
R34 and R35 taken together are -C(R 7 )=C(R 7 )- wherein R 7 and R 7 are as defined
in claim 1.
18. A compound according to any one of claims 1 to 17, wherein:
Q is a group of formula Q 1, or
Q is a group of formula Q2 and Y is O.
19. A compound according to any preceding claim, which is compound A8, A9, A10, A14
or A16:
in each case optionally present as an agrochemically acceptable salt thereof.
20. A herbicidal composition which comprises:
(i) a compound of formula (I), as defined in any of claims 1 to 19, and
(ii) an agrochemically acceptable carrier, diluent and/or solvent; and
(iii) optionally one or more further herbicides and/or optionally a safener.
2 1. A method of controlling grassy monocotyledonous weeds in crops of useful plants,
comprising applying a compound of formula (I), as defined in any of claims 1 to 19, or a
herbicidal composition according to claim 20, to the weeds and/or to the plants and/or
to the locus thereof.