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, cyclohexanedione, cyclohexanetrione orcycloheptanedione compounds, more particularly (alkynyl-phenyl)-substituted and alkanediyl-bridged cyclic dione compounds such as pyrandione, thiopyrandione, piperidinedione, 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. Amongst many compounds

specifically disclosed in WO 01/17972 A2 is compound 2 1.115 ( ^^"^ ), which is
disclosed on page 105 of WO 01/17972 A2.
WO 03/013249 A1 (Bayer AG) and its equivalent US 2005/0054535 A1 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-di ethyl. In WO 03/013249 A1 and US 2005/0054535 A1, the cyclic ketoenol (whose tautomer is a cyclic dione) can in particular be a 3-(substituted-phenyl)-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, etal., 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 A1 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 A1, the cyclic ketoenol (whose tautomer is a cyclic

dione) can in particular be a 3-(substituted-phenyl)-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-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 A1 and WO 2009/074314 A1 (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 ortrione by an aryl-substituted-phenyl or by a heteroaryl-substituted-phenyl.
WO 2010/081755 A1 and WO 2010/08921 1 A1 (both Syngenta Limited) each disclose herbicidally active pyran-3,5-diones, thiopyran-3,5-diones, cyclohexanediones, cycloheptanediones and cyclohexanetriones, each substituted by an aryloxy-substituted-phenyl or by a heteroaryloxy-substituted-phenyl.
WO 2008/1 10308 A1 (Syngenta Participations AG) discloses 2-(substituted-phenyl)-cyclohexane-1 ,3-dione compounds and derivatives, containing a R8-X-(CR6R7)n- substituent (wherein X is O, S, S(O) orS(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-[R8-X-(CR6R7)n-]-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 A1 (Syngenta Participations AG) discloses 2-(substituted-phenyl)-5-(carbon-linked-heterocyclyl)-cyclohexane-l ,3-dione compounds and derivatives, and their use as herbicides. WO 201 0/081 687 A1 (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 A1 (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 A1 and A8 (Syngenta Limited) disclose herbicidally active phenyl-substituted 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 201 0/000773 A1, WO 2010/069834 A1, WO 2010/089210 A1, WO 2010/102848 A land WO 201 1/007146 A1 (all Syngenta Limited et al.)- For example, WO 2010/000773 A1 (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 A1 (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 .026]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 A1 (both Syngenta Limited). Phenyl-substituted 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 A1 (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 A1 (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 orchloroethynyl 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.
Alkanediyl-bridged 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. spirocyclic bicyclic 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 orchloroethynyl 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)
x

(I) wherein:
X is methyl or chlorine (preferably methyl);
R1 is fluorine or bromine (preferably fluorine);
R2 is ethynyl, d-Csalkoxy-, CrCshaloalkoxy-, or d-Csalkoxy-CrCsalkoxy- (preferably
-0-R 2A, wherein R2A is methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl,
or-CH2CH20CH 3; more preferably -0-R 2A, wherein R2A 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
cyclohexane-1 ,3,5-trione-2-yl, a cyclohexane-1 ,3-dione-2-yl, or a cycloheptane-1 ,3-dione-2-
yl, in which each cyclic dione is bridged by alkanediyl, as well as derivatives thereof (e.g.
spirocydic derivatives, and/or enol ketone tautomer derivatives thereof), in particular wherein
Q is as further defined herein, are novel;
and that the exemplified compounds A1, A2, A3, A4, A5, A6, A7, A8, P1, P2, P3, P4 and P5 within this formula (I) and disclosed herein appear to be potent post-emergent herbicides when used against grassy (in particular warm climate grassy) monocotyledonous weeds, when applied at about 250 and/or 30 g/ha post-emergence (e.g. as shown in Biological Examples 1 and 2 hereinafter), or, for exemplified compounds A1, A3, A4, A7, P1, P2 and P4, when applied at 8 g/ha post-emergence with certain adjuvant systems (e.g. see Biological Example 3).

in particular, the results in Biological Example 1A hereinafter appear to show that Compound A1, within the present formula (I), having a 2-fluoro-6-methoxy-4-(prop-i -ynyl)-phenyl moiety attached to a bicyclo[3.2.1]octane-2,4-dione, is a more potent herbicide against the grassy monocotyledonous weeds ALOMY (Alopecurus myosuroides) and ECHCG (Echinochloa crus-galli) than compound B1, having a 2-fluoro-6-methoxy-4-ethynyl -phenyl moiety attached to the same bicyclo[3.2.1]octane-2,4-dione, when applied post-emergence at 30 and 8 g/ha under the conditions stated in Biological Example 1A.

Also, in particular, Compound A1 ( v""^ ), within the presently invented
formula (I), appears at first sight to have higher post-emergence activities at 30 g/ha against the grassy monocotyledonous weeds LOLPE (Lolium perenne), POAAN (Poa annua), BROTE (Bromus tectorum) and SORVU (Sorghum bicolor (L.) Moench ssp. Bicolor, or

Sorghum vulgare Pers.), than those of comparator compound X10 ( ^^ ),
disclosed as compound 2 1.115 on page 105 of WO 01/17972 A2 (see Biological Example 2 hereinafter, and the notes at the end of its post-emergence herbicidal activity results table).
Also, the exemplified compounds A1,A2, A7, P1, P2, P3, P4 and P5 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 certain exemplified compounds including A1, A3, A4, A7, PI , P2 and P4 on soybean. Finally, compounds A1, A2, A7, PI and P5 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;
R1 is fluorine or bromine;
R2 is ethynyl, CrC3alkoxy-, CrC 3haloalkoxy- (in particular CrC 3fluoroalkoxy-), or
d-dalkoxy-d-dalkoxy-;
and Q is a group of formula Q2:
wherein in Q2:
R33 and R36, independently of each other, are hydrogen, C-|-C5alkyl (in particular d -
C4alkyl, e.g. CpC^alkyl), C2-C4alkenyl (in particular C2-C3alkenyl-CH2-, e.g. ethenyl-CH2-),
C2-C4alkynyl (in particular C2-C3alkynyl-CH2-, e.g. ethynyl-CH2-), d-dfluoroalkyl, Cr
Csalkoxyd-Csalkyl, d-dalkylthiod-dalkyl, d-dalkylsulfinyld-dalkyl, Cr
dalkylsulfonyld-dalkyl; d-dcycloalkyl (in particular cyclopropyl); or an unsubstituted 4, 5 or 6 (e.g. 4 or 5) membered monocyclic heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and nitrogen, said heterocyclyl being attached at a ring carbon atom within the heterocyclyl (in particular tetrahydrofuranyl such as tetrahydrofuran-3-yl, ortetrahydropyranyl such as tetrahydropyran-4-yl); provided that no more than one (in particular none) of R33 and R36 is alkenyl, alkynyl, alkoxyalkyi, alkylthioalkyi, alkylsulfinylalkyi, alkylsulfonylalkyi, cycloalkyi or heterocyclyl; and

R34 and R35 taken together are -(CH2)n34- or-(CH2)n35-C(R37a)(R37b)-(CH2)n36-;
wherein R3?a is CrC2alkyl; R37b is hydrogen or CrC2alkyl;
n34 is 1, 2 or 3; and
n35 and n36 are independently 0, 1 or 2 provided that n35 + n36 is 0, 1 or 2; and
Y is O, S, S(O), S(0) 2, N(CrC 2alkyl), N(d-dalkoxy), C(O), CR38R39or-
c R 310 R 311c R 312 R 313_. gnc|
R38 and R39 are, independently of each other: hydrogen, CrC 6alkyl (in particular d -
C4alkyl, e.g. d-dalkyl), C2-C4alkenyl (in particular C2-C3alkenyl-CH2-, e.g. ethenyl-CH2-), C2-
C4alkynyl (in particular C2-C3alkynyl-CH2-, e.g. ethynyl-CH2-), Ci-C2fluoroalkyl, d -
C3alkoxyCi-C3alkyl, Ci-C3alkylthioCrC3alkyl, Ci-C3alkylsulfinylCrC3alkyl, orCr
dalkylsulfonyld-dalkyl; C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two
substituents which independently are C-|-C3alkyl (in particular methyl or ethyl) ord -
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^lky!),
N(CrC2fluoroalkyl), N[C(0)CrC3alkyl], N[C(0)CrC2fluoroalkyl] or N(CrC2alkoxy) moiety;
C3-C6cycloalkyl 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);
d-dcycloalkenyl or d-dcycloalkenyl substituted by one or two d-dalkyl (in particular
methyl) substituents; C3-C6cycloalkyld-C 2alkyl- (in particular d-dcycloalkylmethyl-) or C3-
dcycloalkyld-dalkyl- (in particular d-dcycloalkylmethyl-) 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-dcycloalkylmethyl-) 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(Ci-C2fluoroalkyl), N[C(0)d-dalkyl], N[C(0)C rC2fluoroalkyl] or N(d-C2alkoxy)
moiety; d-dcycloalkyld-dalkyl- (in particular d-dcycloalkylmethyl-) substituted by one
ring substituent being d-dalkoxy (in particular d-dalkoxy) and optionally further substituted by one ring substituent being d-dalkyl (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 d-dalkyl, CrC2fluoroalkyl, d-dalkyl-C(O)-, d-dfluoroalkyl-C(O)-, -C(0)-N(R 6H)(ReJ), SR6E, S(0)R 6E, -S(0) 2-R6E, -N(ReF)(R6G), hydroxy, d-dalkenyl, -C(R6BB)=C(R6c1)(R6C2), d-dalkynyl, -CsC-R6^, d-dalkoxy, CrC2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HC=C-CH2-0-, halogen, cyano ornitro; 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, Ci-C2fluoroalkyl, Ci-C3alkyl-C(0)-, CrC2fluoroalkyl-C(0)- or Ci-C2alkyl-S(0) 2- substituent;
provided that no more than one of R38 and R39 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-C3alkyl), N(CrC2fluoroalkyl), N[C(0)Ci-C 3alkyl], N[C(0)C rC2fluoroalkyl] or N(CrC2alkoxy) moiety; an optionally substituted cycloalkenyl; an optionally substituted cycloalkyl-alkyl-; an optionally substituted cycloalkyl-alkyl- in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(CrC3alkyl), N(CrC2fluoroalkyl), N[C(0)C rC3alkyl], N[C(0)C rC2fluoroalkyl] or N(CrC2alkoxy) moiety; or HetA or HetA-CH2-;
or R38 is hydrogen orCrC2alkyl (in particular H or Me), and R39 is CrC 2alkoxy (in particular methoxy);
or R38 and R39 taken together are -(CH2)n37- or-(CH2)n38-X32-(CH2)n3g-;
wherein X32 is O, S, S(O), S(0) 2, NH, N(CrC3alkyl), N(CrC2fluoroalkyl), N[C(0)C i-C3alkyl], N[C(0)C rC2fluoroalkyl], N(CrC2alkoxy), C(H)(C1-C3alkyl), C(CrC2alkyl)2 orC(H)(Ci-C3alkoxy);
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
R31°, R311, R312 and R313 are independently of each other hydrogen or CrC4alkyl (in particular CrC2alkyl) provided that no more than one of R31°, R311, R312 and R313 is C3-C4alkyl;
and wherein:
R6^ is C-ifluoroalkyl (preferably trifluoromethyl), fluorine, chlorine or bromine;
R6BB R6c1 and R6C2 independently are hydrogen, methyl, dfluoroalkyl (preferably trifluoromethyl), fluorine or chlorine; provided that R6BB, R6°1 and R6C2 in total contain no more than one carbon atom, and R6BB, R6°1 and R6C2 in total comprise no more than one chlorine; and provided that -C(R6BB)=C(R6c1)(R6C2) is not C2-C3alkenyl; and
R6E is Ci-C3alkyl (preferably Ci-C2alkyl such as methyl), Cifluoroalkyl (preferably trifluoromethyl), or-N(R6H)(ReJ);
R6F is -C(0)-Ci-C 2alkyl (preferably -C(O)-methyl), -C(0)-Cifluoroalkyl (preferably -C(O)-trifluoromethyl), -S(0) 2-CrC2alkyl

WO 2014/191535 PCT7EP2014/061207
-9-
(preferably -S(0) 2-methyl), -S(0) 2-C1fluoroalkyl (preferably -S(0) 2-trifluoromethyl), C1-C2alkyl (preferably methyl), or CifluoroalkyI (preferably trifluoromethyl);
R6G and R6 independently are hydrogen, methyl or CifluoroalkyI (preferably trifluoromethyl); and
R6H is hydrogen, Ci-C2alkyl (preferably methyl), or CifluoroalkyI (preferably trifluoromethyl); and
and wherein in Q2:
G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group; or
G is -C(Xa)-Ra, -C(Xb)-Xc-Rb, -C(Xd)-N(Rc)-Rd, -S0 2-Re, -P(Xe)(Rf)-R9, -CH2-Xf-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-C2alkyl, CifluoroalkyI, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano ornitro), or heteroaryl-CH2- or heteroaryl-CH(Ci-C2alkyl)- (in each of which the heteroaryl is optionally substituted by 1,2 or 3 of, independently, Ci-C2alkyl, CifluoroalkyI, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or phenyl-C(0)-CH 2- (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, CrC 2alkyl, CifluoroalkyI, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro); or CrC 6alkoxy-C(0)-CH 2-, CrC 6alkoxy-C(0)-CH=CH-, C2-C7alken-1-yl-CH2-, C2-C7alken-1-yl-CH(Ci-C 2alkyl)-, C2-C4fluoroalken-1-yl-CH2-, C2-C7alkyn-1-yl-CH2-, or C2-C7alkyn-1-yl-CH(Ci-C 2alkyl)-;
wherein Xa, Xb, Xc, Xd, Xe and Xf are independently of each other oxygen or sulfur (in particular oxygen); and wherein
Ra is H, Ci-C2ialkyl, C2-C2ialkenyl, C2-Ci8alkynyl, Ci-Ci 0fluoroalkyl, Ci-Ci 0cyanoalkyl, Ci-Ci 0nitroalkyl, Ci-Ci 0aminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C 5)alkyl, C3-C5alkynyloxy(Ci-C 5)alkyl, Ci-C5alkylthio(Ci-C5)alkyl, C1-C5alkylsulfinyl(C1-C5)alkyl, Cr C5alkylsulfonyl(Ci-C 5)alkyl, C2-C8alkylideneaminoxy(Ci-C 5)alkyl, Ci-C5alkylcarbonyl(d-C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C 5)alkyl, aminocarbonyl(Ci-C 5)alkyl, d -C5alkylaminocarbonyl(Ci-C 5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl, d -C5alkylcarbonylamino(Ci-C 5)alkyl, /V-(Ci-C5)alkylcarbonyl-/V-(Ci-C5)alkylamino(Ci-C 5)alkyl, C3-C6trialkylsilyl(Ci-C 5)alkyl, phenyl(d-C 5)alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, d-C 3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano, ornitro), heteroaryl(Ci-

WO 2014/191535 PCT7EP2014/061207
-10-
C5)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, d -C3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, Ci-C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, ornitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro;
Rb is CrCi 8alkyl, C3-Ci8alkenyl, C3-Ci8alkynyl, C2-Ci0fluoroalkyl, Ci-Ciocyanoalkyl, d -Cl0nitroalkyl, C2-Ci0aminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl, C3-C5alkynyloxy(C1-C5)alkyl, C1-C5alkylthio(C1-C5)alkyl, C1-C5alkylsulfinyl(C1-C5)alkyl, Cr C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, d-dalkylcarbonyl(d-C5)alkyl, C1-C5alkoxycarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, Cr dalkylaminocarbonyl(d-d)alkyl, d-C 8dialkylaminocarbonyl(d-d)alkyl, d -C5alkylcarbonylamino(d-C 5)alkyl, /V-(C-d)alkylcarbonyl-/V-(C -d)alkylamino(C -d)alkyl, d-dtrialkylsilyl(C -d)alkyl, phenyl(C1-d)alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-dfluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, d -C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, d-dalkylthio, d-C 3alkylsulfinyl, Crdalkylsulfonyl, halogen, cyano, ornitro), C3-C5fluoroalkenyl, d-C 8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, d-C 3alkyl, Ci-C3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, Crdalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; and
Rc and Rd are each independently of each other hydrogen, d-doalkyl, C3-d 0alkenyl, d-Ci 0alkynyl, d-Ci 0fluoroalkyl, d-C „ncyanoalkyl, d-C ,nnitroalkyl, d-C ,naminoalkyl, d -
Uyy' U y ' 10 J y ' 10 y ' 10 y '
dalkylamino(d-d)alkyl, d-C 8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl, d -dalkoxy(Ci-d)alkyl, d-dalkenyloxy(d-d)alkyl, C3-dalkynyloxy(d-d)alkyl, C-C5alkylthio(d-C 5)alkyl, d-dalkylsulfinyl(Ci-C 5)alkyl, Ci-dalkylsulfonyl(C rd)alkyl, C2-C8alkylideneaminoxy(d-d)alkyl, d-C 5alkylcarbonyl(d-d)alkyl, Ci-dalkoxycarbonyl(d-d)alkyl, aminocarbonyl(d-d)alkyl, Ci-dalkylaminocarbonyl(d-d)alkyl, C2-C8dialkylaminocarbonyl(d-d)alkyl, d-dalkylcarbonylamino(Ci-d)alkyl, /V-(d-d)alkylcarbonyl-/V-(C 2-d)alkylaminoalkyl, C3-C6trialkylsilyl(d-C 5)alkyl, phenyl(d-C 5)alkyl

WO 2014/191535 PCT7EP2014/061207
- 11 -
(wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, C-C3alkyl, d -C3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, C-C3alkylthio, CrC 3alkylsulfinyl, d -C3alkylsulfonyl, halogen, cyano, ornitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, C-C3alkyl, C-C3fluoroalkyl, d -C3alkoxy, C-C3fluoroalkoxy, C-C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, ornitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, C-C3alkoxy, C-i-C3fluoroalkoxy, halogen, cyano ornitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, C-C3fluoroalkyl, C-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1,2 or 3 of, independently, Ci-C3alkyl, Ci-C3fluoroalkyl, d -dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-dalkoxy, d -dfluoroalkoxy, halogen, cyano ornitro; phenylamino or phenylamino substituted by 1,2 or 3 of, independently, d-C 3alkyl, C-C3fluoroalkyl, C-C3alkoxy, C-C3fluoroalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by 1,2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, Ci-C3alkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; orC3-dcycloalkylamino, di(C3-C7cycloalkyl)amino or C3-C7cycloalkoxy;
or Rc and Rd, together with the nitrogen to which they are bonded, form an unsubstituted 4, 5, 6 or 7 (e.g. 5 or6) membered ring, optionally containing one heteroatom selected from O orS; and
Re is d-doalkyl, C2-d 0alkenyl, d-doalkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d -C„nnitroalkyl, d-C „naminoalkyl, d-C ,-alkylamino(d-C Jalkyl, d-ddialkylamino(C 1-d)alkyl,
10 y ' 10 y ' 5 J v 5)y' J \ -| / y >
d-dcycloalkyl(d-d)alkyl, d-dalkoxy(d-d)alkyl, d-dalkenyloxy(d-d)alkyl, C3-
dalkynyloxy(d-d)alkyl, C1-dalkylthio(C 1-d)alkyl, C1-dalkylsulfinyl(C 1-d)alkyl, Cr
dalkylsulfonyl(d-d)alkyl, d-dalkylideneaminoxy(C 1-d)alkyl, d-dalkylcarbonyl(d-
C5)alkyl, d-dalkoxycarbonyl(d-d)alkyl, aminocarbonyl(d-d)alkyl, d -
dalkylaminocarbonyl(d-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, d -
C5alkylcarbonylamino(d-C 5)alkyl, V -(Ci-d)alkylcarbonyl-/V (Ci-d)alkylamino(Crd)alkyl, d-C 6trialkylsilyl(d-d)alkyl, phenyl(d-d)alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, Crdalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen , cyano, or nitro), heteroaryl(d-d)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, d -C3alkyl, Ci-C3fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen , cyano, or nitro), C2-C5fluoroalkenyl, d-C 8cycloalkyl; phenyl or

WO 2014/191535 PCT7EP2014/061207
- 12-
phenyl substituted by 1,2 or 3 of, independently, C-C3alkyl, d-C 3fluoroalkyl, d-dalkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, CrC 3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, C-C3fluoroalkoxy, 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 ordiheteroarylamino substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-C 3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d -dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1,2 or 3 of, independently, d-dalkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d -dfluoroalkoxy, halogen, cyano or nitro; or C3-dcycloalkylamino, di(C3-dcycloalkyl)amino, d-dcycloalkoxy, d-C 10alkoxy, d-d 0fluoroalkoxy, d-dalkylamino or dKd-dalkyOamino; Rf and R9 are are each independently of each other d-C „nalkyl, C2-d 0alkenyl, C2-
i J 10 y z U y ' z
Cnalkynyl, d-C ,nalkoxy, d-C „nfluoroalkyl, d-C ,ncyanoalkyl, d-C ,nnitroalkyl, d -
10 J J ' 10 J ' 10 J ' 10 J J ' 10 J '
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, Cr
dalkylsulfonyl(d-d)alkyl, d-dalkylideneaminoxy(d-d)alkyl, CrC 5alkylcarbonyl(Cr
d)alkyl, C-dalkoxycarbonyl(d-d)alkyl, aminocarbonyl(d-d)alkyl, d -
dalkylaminocarbonyl(d-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, d -
C5alkylcarbonylamino(d-C 5)alkyl, /V-(C1-d)alkylcarbonyl-/V-(d-d)alkylaminoalkyl, C3-dtrialkylsilyl(C -C5)alkyl, phenyl(C1-d)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C 3alkylsulfonyl, halogen , cyano, or nitro), heteroaryl(d-d)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, d -dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, d-C 3alkylthio, d-C 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, d-C 3alkyl, C-C3fluoroalkyl, C-C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, C-C3alkyl, C-C3fluoroalkyl, 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 ordiheteroarylamino substituted by 1,2 or3 of, independently, d-C 3alkyl, d-dfluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; phenylamino or

WO 2014/191535 PCT7EP2014/061207
-13-
phenylamino substituted by 1,2 or 3 of, independently, C-C3alkyl, d-C 3fluoroalkyl, d -C3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1,2 or 3 of, independently, CrC 3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, d -C3fluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di(C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, Ci-Ci 0fluoroalkoxy, Ci-C5alkylamino ordi(Ci-C4alkyl)amino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by 1, 2 or 3 of, independently, Ci-C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; and
Rh is Ci-Ci 0alkyl, C3-Ci0alkenyl, C3-Ci0alkynyl, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d -
Cl0nitroalkyl, C2-Ci0aminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl,
C3-C7cycloalkyl(C1-C5)alkyl, C1-C5alkoxy(C1-C5)alkyl, C3-C5alkenyloxy(C1-C5)alkyl, C3-
C5alkynyloxy(C1-C5)alkyl, C1-C5alkylthio(C1-C5)alkyl, C1-C5alkylsulfinyl(C1-C5)alkyl, Cr
C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, CrC 5alkylcarbonyl(Cr
d)alkyl, C1-dalkoxycarbonyl(C 1-d)alkyl, aminocarbonyl(d-d)alkyl, d -
dalkylaminocarbonyl(d-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, d -
dalkylcarbonylamino(C -d)alkyl, /V-(C1-d)alkylcarbonyl-/V-(C 1-d)alkylamino(C -d)alkyl, C3-C6trialkylsilyl(CrC 5)alkyl, phenyl(C1-d)alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, Crdalkylthio, d-C 3alkylsulfinyl, d-C 3alkylsulfonyl, halogen, cyano or nitro), heteroaryl(d-d)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, d -dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, Crdalkylthio, d-C 3alkylsulfinyl, Crdalkylsulfonyl, halogen, cyano or nitro), phenoxy(d-C 5)alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d -dalkoxy, Crdfluoroalkoxy, Crdalkylthio, d-C 3alkylsulfinyl, d-C 3alkylsulfonyl, halogen, cyano or nitro), heteroaryloxy(CrC 5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, Cr dalkylthio, CrC 3alkylsulfinyl, Crdalkylsulfonyl, halogen, cyano or nitro), C3-C5fluoroalkenyl, d-dcycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, d-C 3alkyl, d -C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-dfluoroalkyl, d -dalkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; Ci-C6alkyl-C(0)-; or phenyl-C(O)-wherein the phenyl is optionally substituted by 1 or 2 of, independently, d -dalkyl, CifluoroalkyI, CrC 2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro;

WO 2014/191535 PCT7EP2014/061207
- 14-
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, ordialkylaminocarbonyl, et al.) can be straight-chained or branched. Typically, the alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, ie/f-butyl, n-pentyl, neopentyl, orn-hexyl. The alkyl groups can e.g. be CrCealkyl groups (except where already defined more narrowly), but are preferably C-i-C4alkyl orCr 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)-configu ration. 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 Cr C3fluoroalkyl or C1-C2fluoroalkyl (preferably Cifluoroalkyl), such as CF3, CHF2, CH2F, CH3CHF-, CF3CH2-, CHF2CH2-, CH2FCH2-, CHF2CF2- or(CH3)2CF-. Fluoroalkoxy is typically Ci-C3fluoroalkoxy or Ci-C2fluoroalkoxy (preferably Cifluoroalkoxy), such as CF30 , CHF20 , CH2FO, CH3CHFO-, CF3CH20-, CHF2CH20- orCH2FCH20-.
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

WO 2014/191535 PCT7EP2014/061207
-15-
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 ortwo (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 oroxo (=0), and/oris optionally substituted by one CrCsalkyl (e.g. C1-C2alkyl), C1-C2fluoroalkyl ord-Csalkoxy (e.g. CrC 2alkyl or Ci-C2fluoroalkyl) substituent on a ring nitrogen if present, and/or is optionally substituted by one ortwo oxo (=0) substituents on a ring sulfur if present.
Preferably, a cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl orcyclohexyl. (Cycloalkyl)alkyl is preferably (cycloalkyl)methyl such as (C3-C6cycloalkyl)methyl in particular cyclopropylmethyl. Preferably, cycloalkenyl is cyclopentenyl orcyclohexenyl.

WO 2014/191535 PCT7EP2014/061207
-16-
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 Ci-Ci8alkylamines, 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-n-amylamine, di-isoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, A/,/V-diethanolamine, /V-ethylpropanolamine, N-butylethanolamine, 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-sec-butylamine, 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, o, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and 0-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and di-isopropylamine.
Preferred quaternary ammonium bases suitable for salt formation correspond, for example, to the formula [N(Ra Rb RcRd)]OH, wherein Ra, Rb, Rc and Rd are each independently of the others hydrogen, d-C 4alkyl. 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 [SReRfR g]OH, wherein Re, Rfand R are each independently of the others Cr C4alkyl. Trimethylsulfonium hydroxide is especially preferred. Suitable sulfonium bases may

WO 2014/191535 PCT7EP2014/061207
- 17-
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 orsulfonium 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 orremoveable groups) within G (for example, without limitation, the latentiating groups where G is -C(Xa)-Ra or-C(Xb)-Xc-Rb, etal.) 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 orfollowing (preferably during orfollowing) 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, R1, R2, R2A, R6^, R6BB, R6C1, R6C2, R6E,
R
6F D6G D6H D6J D33 D34 D35 D36 D37 D37a D37b D38 D39 D310 D311 D312 D313 Da Db Dc ,r\,r\,r\,r\,r\,r\,r\,r\,r\ ,r\ , r\ , r\ , r\ ,l\ ,r\ ,r\ , r\ , r\ , r\ ,
Rd, Re, Rf, R9, Rh, Xa, Xb, Xc, Xd, Xe, Xf, Q, V, HetA, X32, n34, n35, n36, 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 oryet more preferred, particularly or highly preferred, most preferred and all similar terms. For the avoidance of doubt, preferred, suitable and/or particular

WO 2014/191535 PCT7EP2014/061207
-18-
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, R1 is fluorine. In a further preferable embodiment of the invention, R1 is bromine.
Therefore, most preferably, X is methyl, and R1 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 R1 is bromine.
As described above, R2 is ethynyl, C-i-C3alkoxy-, C-i-C3haloalkoxy- (in particular Cr C3fluoroalkoxy-), or d-Csalkoxy-CrCsalkoxy-.
In one embodiment, R2 is ethynyl.
Preferably, R2 is -0-R 2/, wherein R2A is C1-C3alkyl, d-dhaloalkyl (in particular Cr C3fluoroalkyl), or d-C 3alkoxy-d-C 3alkyk Where R2A is Ci-C3alkyl, R2A being methyl or ethyl is preferred. Where R2A is C-C3haloalkyl, R2A being C-C3fluoroalkyl is preferred (more preferably Ci-C2fluoroalkyl, even more preferably C-ifluoroalkyl). Where R2A is CrC 3haloalkyl or CrC 3fluoroalkyl, more specifically, R2A being trifluoromethyl, difluoromethyl, or trifluoroethyl (e.g. 2,2,2-trifluoroethyl) is especially preferred, most particularly trifluoromethyl or difluoromethyl. Where R2A is Ci-C 3alkoxy-Ci-C 3alkyl-, -CH2CH2OCI-l3 (i.e. 2-methoxyethyl-) is preferred. In these preferred embodiments, preferably R1 is fluorine and/or X is methyl.
Therefore, more preferably, in all aspects and/or embodiments of the invention, R2 is -0-R 2A, wherein R2A 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 R1 is fluorine and/or X is methyl.
Even more preferably, in all aspects and/or embodiments of the invention, R2 is -0-R 2A, wherein R2A is methyl, ethyl or C-ifluoroalkyl, in particular methyl, ethyl, trifluoromethyl or difluoromethyl. In these even more preferred embodiments, preferably R1 is fluorine and/or X is methyl.
Most preferably, in all aspects and/or embodiments of the invention, R2 is -0-R 2A, wherein R2A is methyl. In this most preferred embodiment, preferably R1 is fluorine and/or X is methyl.

WO 2014/191535 PCT7EP2014/061207
-19-
Therefore, most preferably, in all aspects and/or embodiments of the invention, X is methyl, R1 is fluorine, and R2 is -0-R 2A wherein R2^ 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; orG is -C(Xa)-Ra,-C(Xb)-Xc-Rb,-S0 2-Re, or-CH2-Xf-Rh; wherein Xa,Xb,Xc,Xf, Ra, Rb, 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; orG is -C(Xa)-Ra or-C(Xb)-Xc-Rb, wherein Xa, Ra, Xb, Xc and Rb are as defined herein.
In a particular embodiment, G is a group -C(Xa)-Ra or -C(Xb)-Xc-Rb, wherein Xa, Ra, Xb, Xc and Rb are as defined herein.
Preferably, e.g. in all aspects and/or embodiments of the invention, Xa,Xb,Xc,Xd,Xe and/or Xf are oxygen; and/or Xc is sulfur.
More preferably, Xa, Xb, Xd, Xe and Xf are oxygen; and Xc is oxygen or sulfur. Even more preferably, Xa, Xb, Xc, Xd, Xe and Xf are oxygen.
Preferably, Ra is Ci-C10alkyl (e.g. Ci-C6alkyl), C2-C6alkenyl (e.g. C2-C4alkenyl), C2-
C6alkynyl (e.g. C2-C4alkynyl), C3-C6cycloalkyl or d-dalkoxyd-dalkyl. 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 ornitro; or heteroaryl orheteroaryl 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-C6alkynyl (e.g. C2-C4alkynyl), d-C 6cycloalkyl, d-dalkoxyd-dalkyl, d-dcycloalkylCialkyl; 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.

WO 2014/191535 PCT7EP2014/061207
-20-
Preferably, Rb is Ci-C10alkyl (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-C4alkoxyCi-C4alkyl. Alternatively, preferably, Rb is 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-C3fluoroalkyl (e.g. CifluoroalkyI), Ci-C3alkoxy (e.g. Cialkoxy), Ci-C3fluoroalkoxy (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-C3alkyl (e.g. Cialkyl), Ci-C3fluoroalkyl (e.g. CifluoroalkyI), Ci-C3alkoxy (e.g. Cialkoxy), Ci-C3fluoroalkoxy (e.g. Cifluoroalkoxy), halogen (e.g. fluorine, chlorine or bromine), or cyano (in which the heteroaryl preferably consists of a single ring).
More preferably, Rb is C-pCioalkyl (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-C4alkoxyCi-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-C3fluoroalkyl (e.g. CifluoroalkyI), Ci-C3alkoxy (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 orC-|-C4alkyl), Ci-Ci 0fluoroalkyl (e.g. Cr C3fluoroalkyl); or phenyl or phenyl substituted by 1,2 or 3 (e.g. 1 or 2) of, independently, Cr C3alkyl (e.g. Cialkyl), Ci-C3fluoroalkyl (e.g. CifluoroalkyI), Ci-C3alkoxy (e.g. Cialkoxy), Cr C3fluoroalkoxy (e.g. Cifluoroalkoxy), halogen (e.g. fluorine, chlorine or bromine), cyano or nitro.
Preferably, Rh is Ci-Ci 0alkyl (e.g. Ci-C6alkyl orCi-C4alkyl), Ci-Ci 0fluoroalkyl (e.g. Cr C3fluoroalkyl) or C-rC6alkyl-C(0)- (e.g. Ci-C4alkyl-C(0)-). In particular, Re is Ci-Ci0alkyl (e.g. C-|-C6alkyl or Ci-C4alkyl).
When G is -C(Xa)-Ra or-C(Xb)-Xc-Rb, then preferably Xa and Xb are oxygen, and Xc is oxygen or sulfur, Ra is CrCioalkyl (e.g. CrC 6alkyl), C2-C6alkenyl (e.g. C2-C4alkenyl), C2-C6alkynyl (e.g. C2-C4alkynyl), C3-C6cycloalkyl or Ci-C4alkoxyCi-C4alkyl; and Rb is CrCioalkyl (e.g. CrC6alkyl), 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-C4alkoxyCi-C4alkyl.

WO 2014/191535

PCT7EP2014/061207

21
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.
In a particularly preferable embodiment of the invention, the compound of formula (I) is a compound described in any of Tables 1, 2, 3, 4, 5 or6, as described and/or illustrated herein, optionally present (e.g. where chemically possible) as an agrochemically acceptable salt thereof.
In a more particularly preferable embodiment of the invention, the compound of formula (I) is any one of the compounds A1 to A7, or A8, orA9 or A10, or P1 to P5, 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 particularly preferable embodiment of the invention, the compound of formula (I) is any one of the compounds A1 to A7, orA8, or P1 to P5, 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 the present invention, Q is a subgroup of formula Q2 as defined above, and so a compound of formula (I) has the general structure (I-2)

(I-2).

In all aspects and/or embodiments of the invention, R34 and R35 taken together are -(CH2) - or-(CH2) -C(R37a)(R37b)-(CH2) -.
v z'n34 v z'n35 v 'v ' v z'n36
C2a
j1-C2a
In the present invention, R37a is C-C-alkyl; and R37b is hydrogen orC-C-alkyl.

WO 2014/191535 PCT7EP2014/061207
-22-

In all aspects and/or embodiments of the invention:
R34 and R35 taken together are -(CH2)n34- or-(CH2)n35-C(R 7a)(R 7 )-(CH2)n36-; wherein R37a is Ci-C2alkyl; R37b is hydrogen or Ci-C2alkyl; n34 is 1,2 or 3 (preferably 2 or 3); and
n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 0, 1 or2 (preferably 1 or2).
Preferably, n34 is 2 or 3.
Preferably, n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 1 or2.
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, R33 and/or R36, independently of each other, are hydrogen, C-|-C4alkyl (e.g. Ci-C2alkyl), C2-C4 alkynyl (in particular C2-C3alkynyl-CH2-, e.g. ethynyl-CH2-), d-CsalkoxyCrCsalkyl, Ci-C3alkylthioCi-C 3alkyl, Ci-C3alkylsulfinylCi-C 3alkyl, Ci-C3alkylsulfonylCi-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, ortetrahydropyranyl such as tetrahydropyran-4-yl); provided that no more than one (in particular none) of R33 and R36 is alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
i2) - or -(CH2) -C(R )(R ■ )-(CH2)n36 C2alkyl; R is hydrogen or C-C2a
and n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 0, 1 or2 (preferably 1 or2).
More preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, R33 and/or R36, independently of each other, are hydrogen, Ci-C4alkyl (in particular Cr C2alkyl), C2-C4alkynyl (in particular C2-C3alkynyl-CH2-, e.g. ethynyl-CH2-), Ci-C3alkoxyCrC 3alkyl (in particular Ci-C2alkoxyCrC 2alkyl), Ci-C3alkylthioCrC 3alkyl (in particular Ci-C2alkylthioCrC 2alkyl), Ci-C3alkylsulfinylCrC 3alkyl (in particular Ci-C2alkylsulfinylCrC 2alkyl), CrC 3alkylsulfonylCi-C 3alkyl (in particular Ci-C2alkylsulfonylCrC 2alkyl); C3-C4cycloalkyl (in particular cyclopropyl); or an unsubstituted 4, 5 or6 (e.g. 4 or5) membered monocyclic heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and nitrogen, said heterocyclyl being attached at
wherein R37a is Ci-C2alkyl; R37b is hydrogen or C-|-C2alkyl; n34 is 1,2 or 3 (preferably 2 or 3);
and/or R34 and R35 taken together are -(CH9)n^A- or-(CH2)n::,fi-C(R37a)(R37b)-(CH2)n36-;

WO 2014/191535 PCT7EP2014/061207
-23-
a ring carbon atom within the heterocyclyl (in particular tetrahydrofuranyl such as tetrahydrofuran-3-yl, ortetrahydropyranyl such as tetrahydropyran-4-yl); provided that no more than one (in particular none) of R33 and R36 is alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
and/or R34 and R35 taken together are -(CH2)- or-(CH2) -C(R37a)(R37b)-(CH2)36-;
^ v z'n34 v z'n35 v 'v ' v z'
wherein R37a is Ci-C2alkyl; R37b is hydrogen or CrC2alkyl; n34 is 2 or 3; and n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 1 or2.
Still more preferably, R33 and/or R36, independently of each other, are hydrogen, CrC 3alkyl (in particular Ci-C2alkyl such as methyl) or Ci-C3alkoxyCi-C3alkyl (in particular Ci-C2alkoxyCrC 2alkyl); provided that no more than one (in particular none) of R33 and R36 is alkoxyalkyl; and/or R34 and R35 taken together are -(CH2) - or-(CH2) -C(R37a)(R37b)-(CH2)-; wherein R37a is Ci-C2alkyl; R37b is hydrogen
v z'n34 v z'n35 v 'v ' v z'n36 ' z J ' J ^
orCi-C2alkyl; n34 is 2 or 3; and n35 and n36 are independently 0, 1 or 2 provided that n35 + n36 is 1 or 2.
Even more preferably, R33 and/or R36, independently of each other, are hydrogen or Cr C2alkyl (preferably hydrogen or methyl); and/or R34 and R35 taken together are -(CH2)- wherein n34 is 2 or 3, and more preferably n34 is 2.
v z'n34 ' J
Most preferably (especially when Y is CR38R39or-CR310R311CR3l2R313-), R33 and R36 are hydrogen; and/or R34 and R35 taken together are -(CH2)- wherein n34 is 2 or 3, and R33 and
J ^ ' c* \ z'n34
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 or4, still more preferably 3 or4, most preferably all four) of R33 and R36, independently of each other, are hydrogen orC-C 4 alkyl (e.g. H or Ci-C3 alkyl, or H or C-C2alkyl); 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), CR38R39 or-CR 310R311CR312R313-. More preferably, Y is O, C(O),
CR38R39or_CR3ioR3l1CR3i2R3i3_ Even more preferab |y , Y js O or CR38R39, in particular Y is
O or CH 2 . Most preferably, Y is CR38R 39 , in particular Y is CH 2 .
Preferably, e.g. in all aspects and/or embodiments of the invention, in R38 and R39, one or both of R38 and R39 is or are hydrogen; or R38 and R39 taken together are -(CH2) - or
J ^ ' ^ v z'n37
preferably -(CH2), -X32-(CH2) „-. In this embodiment, preferably Y is CR38R39 and/or
r J v z'n38 v z'n39 ' r J
preferably X32 is O.

WO 2014/191535 PCT7EP2014/061207
-24-
In one particular embodiment when Q is Q2, R38 and R39 are taken together and are -(CH2)n37- or-(CH2)n38-X32-(CH2)n39-. In this embodiment, preferably Y is CR38R39 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)(CrC 3alkyl), C(CrC2alkyl)2 or C(H)(CrC3alkoxy). 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-dalkylsulfinyld-dalkyl,
or d-dalkylsulfonyld-dalkyl;
d-C 6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which independently are d-C 3 alkyl (in particular methyl or ethyl) or d-C 2 luoroalkyl, and in which one ring CH2 moiety of a C4-C6cycloalkyl is optionally (e.g. preferably) replaced by an oxygen or sulfur atom orbyaS(O), S(0) 2, NH, N(d-C 3alkyl), N(d-C 2fluoroalkyl), N[C(0)d-C 3alkyl], N[C(0)d-dfluoroalkyl] or N(d-dalkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being d-C 3alkoxy (in particular d-C 2alkoxy) and optionally further substituted by one substituent being d-C 2alkyl (in particular methyl);
C3-C6cycloalkyld-C 2alkyl- (in particular C3-C6cycloalkylmethyl-) or d-dcycloalkyld-dalkyl- (in particular C3-dcycloalkylmethyl-) 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- (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(d-C 2alkyl), N(d-dfluoroalkyl), N[C(0)d-dalkyl], N[C(0)d-dfluoroalkyl] or N(d-C 2alkoxy) moiety;
d-C 6cycloalkylCrdalkyl- (in particular C3-C6cycloalkylmethyl-) substituted by one ring substituent being d-C 3alkoxy (in particular d-C 2alkoxy) and optionally further substituted by one ring substituent being d-C 2alkyl (in particular methyl); or

WO 2014/191535 PCT7EP2014/061207
-25-
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 or2, e.g. 1) ring-carbon substituents independently being d-C3alkyl (e.g. CrC 2alkyl), CrC 2fluoroalkyl, CrC 3alkyl-C(0)-, CrC 2fluoroalkyl-C(0)-, hydroxy (including any oxo tautomer), C2-C3alkenyl (e.g. ethenyl or prop-1-enyl), C2-C3alkynyl (e.g. ethynyl or prop-1-ynyl), C-i-C3alkoxy (e.g. C-i-C2alkoxy), Cr 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 Ci-C3alkyl, C-i-C2fluoroalkyl, C-i-C3alkyl-C(0)-, C-i-C2fluoroalkyl-C(0)- or CrC2alkyl-S(0) 2- substituent;
provided that no more than one of R38 and R39 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-C3alkyl), N(C-|-C2fluoroalkyl), N[C(0)C-|-C3alkyl], N[C(0)C-|-C2fluoroalkyl] or N(C-|-C2alkoxy) moiety; an optionally substituted cycloalkenyl; an optionally substituted cycloalkyl-alkyl-; an optionally substituted cycloalkyl-alkyl- in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C-|-C3alkyl), N(C-|-C2fluoroalkyl), N[C(0)C rC3alkyl], N[C(0)C rC2fluoroalkyl] or N(C-|-C2alkoxy) moiety; or HetA or HetA-CH2-;
or R38 is hydrogen or C-|-C2alkyl (in particular H or Me), and R39 is CrC 2alkoxy (in particular methoxy);
or R38 and R39 taken together are -(CH2)- or-(CH2), -X32-(CH2) „-.
° v z'n37 v z'n38 v z'n39
In the above preferred embodiment, preferably Y is CR38R39and/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 orC-C2alkyl (preferably H or Me, more preferably hydrogen); and R39 is:
Ci-C2alkoxy (in particular methoxy);
C2-C3alkynyl-CH2- (in particular ethynyl-CH2-);
C-i-C3alkoxyCrC 3alkyl;
C-i-C3alkylthioCrC 3alkyl (preferably C-i-C2alkylthio-CH2CH2- or more preferably CrC 2alkylthio-CH(Me)CH 2-);
C-C3alkylsulfinylC rC3alkyl;
C-C3alkylsulfonylCrC 3alkyl;

WO 2014/191535 PCT7EP2014/061207
-26-
C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one ortwo substituents which independently are CrC 3alkyl (in particular methyl orethyl) or Ci-C2fluoroalkyl, and in which one ring CH2 moiety of a C4-C6cycloalkyl is optionally (e.g. preferably) replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(CrC 3alkyl), N(CrC2fluoroalkyl), N[C(0)CrC 3alkyl], N[C(0)Ci-C 2fluoroalkyl] or N(Ci-C2alkoxy) moiety (or more preferably is replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(Ci-C3alkyl) or N(Ci-C2alkoxy) moiety; or still more preferably is replaced by an oxygen or sulfur atom);
C3-C6cycloalkyl substituted by one substituent being Ci-C3alkoxy (in particular CrC 2alkoxy) and optionally further substituted by one substituent being Ci-C2alkyl (in particular methyl);
C3-C6cycloalkylmethyl- or C3-C6cycloalkylmethyl- substituted by one ortwo 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 optionally (e.g. preferably) replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C1-C2alkyl), N(Cr C2fluoroalkyl), N[C(0)C ^C3alkyl], N[C(0)C rC2fluoroalkyl] or N(C-|-C2alkoxy) moiety (or more preferably is replaced by an oxygen or sulfur atom or by a N[C(0)CrC 3alkyl] or N[C(0)C rC2fluoroalkyl] moiety);
C3-C6cycloalkylmethyl- substituted by one ring substituent being Ci-C3alkoxy (in particular Ci-C2alkoxy) and optionally further substituted by one ring substituent being C-C2alkyl (in particular methyl); or
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 or2, e.g. 1) ring-carbon substituents independently being C-C3alkyl (in particular C-C2alkyl), C-i-C2fluoroalkyl (in particular Cifluoroalkyl), d-Csalkyl-C^O)-, CrC^luoroalkyl-CiO)-, hydroxy (including any oxo tautomer), C2-C3alkenyl (in particular ethenyl or prop-1-enyl), C2-C3alkynyl (in particular ethynyl or prop-1-ynyl), C-i-C3alkoxy (in particular Ci-C2alkoxy), d-Cyiuoroalkoxy (in particular Cifluoroalkoxy), halogen (in particular fluorine or chlorine), cyano ornitro; 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 CrC2alkyl-S(0) 2- substituent;
or R38 and R39 taken together are -(CH2) - or-(CH2), -X32-(CH2) „-.
° v z'n37 v z'n38 v z'n39
In the above preferred embodiment, preferably Y is CR38R39and/or preferably X32 is O.

WO 2014/191535 PCT7EP2014/061207
-27-
Even 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:
Ci-C 3alkylthioCi-C 3alkyl (preferably Ci-C 2alkylthio-CH 2CH2- or more preferably Ci-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(CrC 3alkyl), N(CrC2fluoroalkyl), N[C(0)C 1-C3alkyl], N[C(0)C 1-C2fluoroalkyl] or N(C-C2alkoxy) moiety (or preferably is replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C1-C3alkyl) or N(C1-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 C1-C3alkyl (in particular C-C2alkyl) or C-i-C2fluoroalkyl, and in which one ring CH2 moiety of a C4-C6cycloalkylmethyl- is replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C1-C2alkyl), N(C1-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 rC3alkyl] or N[C(0)C rC2fluoroalkyl] 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 C-C3alkyl (in particular C1-C2alkyl), C-i-C2fluoroalkyl (in particular dfluoroalkyl), d-Csalkyl-C^O)-, d-dfluoroalkyl-C(O)-, hydroxy (including any oxo tautomer), C2-C3alkenyl (in particular ethenyl or prop-1-enyl), C2-C3alkynyl (in particular ethynyl or prop-1-ynyl), C-i-C3alkoxy (in particular d-dalkoxy), d-dfluoroalkoxy (in particular Cifluoroalkoxy), halogen (in particular fluorine or chlorine), cyano ornitro; 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-C 3alkyl, CrC 2fluoroalkyl, Ci-C 3alkyl-C(0)-, Ci-C 2fluoroalkyl-C(0)- or CrC2alkyl-S(0) 2-substituent;
or R38 and R39 taken together are -(CH2)n37- or-(CH2)n38-X32-(CH2)n39-.
In the above even more preferred embodiment, preferably Y is CR38R39 and/or preferably X32 is O.

WO 2014/191535

PCT7EP2014/061207

28
In one most preferable embodiment (which e.g. can apply to all aspects and/or embodiments of the invention when Q is Q2), R38 and R39 are, independently of each other, hydrogen orCi-C3alkyl (preferably hydrogen orCrC 2alkyl, more preferably hydrogen or methyl, most preferably hydrogen). In this embodiment, preferably, Y is CR38R39.
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 3 alkylthioCi-C 3 alkyl. In this embodiment, R39 preferably is Ci-C2alkylthio-CH2CH2- or more preferably is Ci-C 2 alkylthio-CH(Me)CH 2 -. In this embodiment, preferably, Y is CR38R 39 .
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(Cr 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)C -|-C 2 fluoroalkyl] moiety). In this embodiment, preferably, Y is CR38R 39 .
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 sub-formulae V-i, V2,V,, V., V5, V6, V7,V„, V,,, V„, V,Q, V„„, V.„, V.,, V.., V.,, Vov, Von, Vnn orV„nv
" z' 3' 4' 0' b' I' 33' 34' 37' 38' 41' 42' 43' 44' 47' 87' 89' 90 107

o
(Vi)

(V2)

-s
(V3)

(V4)

"CT ^A
(V5)

(Vg)

(V7)

(Ve)

(Vg)

(Vio)

WO 2014/191535

PCT/EP2014/061207

29





o=s
9A/
R
o=s
II O
(V38)
o

(V41)
N /
9A/

R

(V42)

,9A

(V43)

(V44)
R'
9A

(V47)

(V87)

(V89)

(V90)

(V107)

wherein: A is the position of attachment to the -methyl- moiety; and R9A is hydrogen, C-|-C2alkyl (e.g. methyl), CrC2fluoroalkyl (e.g. Cifluoroalkyl), -C(0)C rC3alkyl (e.g. -C(O)-methyl), -C(0)C rC2fluoroalkyl (e.g. -C(O)Cifluoroalkyl) or CrC2alkoxy.
More preferably, V is one of the sub-formulae Vi, V2, V4, V6, V7, V„, V,,, V„„, V._, V.,,
r J' ' 2? 4' b' I' 33' 34' 41' 42' 43'
V.., Vov, V89 orVnn. Even more preferably, V is one of the sub-formulae V2, V6, V7, V„, V,,,
44' 87' "90 r yi ^1 5' p 33' 34'
V,,, V._, V.,, V.., Vov, Von or Vnn.
41' 42' 43' 44' 87' 89 90
Yet more preferably, V is one of the sub-formulae V2, V7, Vov orVnn. Further more
r J ' Z' I' 87 90
preferably, V is one of the sub-formulae V2, V7 orVnn.
r ' ' Z' I 90
Most preferably, V is sub-formula V7.
Preferably, R9A is -C(0)C rC3alkyl (e.g. -C(O)methyl) or-C(0)C rC2fluoroalkyl (e.g. -C(O)Cifluoroalkyl).

O
In one preferable embodiment of the invention (which e.g. can apply to all aspects and/or embodiments of the invention), R38 is hydrogen, and R39 is tetrahydro-2/-/-pyran-4-yl (
) or
(tetrahydro-2/-/-pyran-4-yl)-methyl-. In this embodiment, preferably, Y is R 39 is (tetrahydro-2H-pyran-4-yl)-methyl-, then R39 is V7-methyl- wherein V7
38R 39.
C R
When

O

is
A wherein A is the position of attachment to the -methyl- moiety. In another preferable embodiment (which e.g. can apply to all aspects and/or embodiments of the invention when Q is Q2), R38 is hydrogen and R39 is HetA or HetA-CH 2 - as defined herein. In this embodiment, more preferably, R38 is hydrogen and R39 is HetA as defined herein. In this embodiment, preferably, Y is CR38R39.

WO 2014/191535 PCT7EP2014/061207
-30-
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is a heteroaryl (in particular monocyclic heteroaryl), attached at a ring-carbon, which is optionally substituted by 1,2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents independently being CrC 2alkyl, Cifluoroalkyl, CrC 2alkyl-C(0)-, Cifluoroalkyl-C(O)-, hydroxy (including any oxo tautomer), ethynyl, prop-1-ynyl, CrC 2alkoxy, C-ifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro, provided that any chlorine, bromine, alkoxy orfluoroalkoxy is not substituted at any ring-carbon bonded directly to a ring-nitrogen of the heteroaryl; and/or, in the case of a 5-membered heteroaryl ring containing a ring-nitrogen atom not partaking in a C=N ring double bond, the heteroaryl is optionally substituted on the ring-nitrogen atom not partaking in a C=N ring double bond by one Ci-C3alkyl, C-rC2fluoroalkyl, C-rC3alkyl-C(0)-, C-rC2fluoroalkyl-C(0)- or Ci-C2alkyl-S(0) 2- substituent.
More preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is a heteroaryl (in particular monocyclic heteroaryl), attached at a ring-carbon, which is optionally substituted by 1 or 2 (in particular 1) ring-carbon substituents independently being C-C2alkyl (in particular methyl), Cifluoroalkyl (in particular CF 3), Ci-C 2 alkyl-C(0)- (in particular Me-C(O)-), Cifluoroalkyl-CtO)-, ethynyl, prop-1-ynyl, fluorine or cyano; and/or, in the case of a 5-membered heteroaryl ring containing a ring-nitrogen atom not partaking in a C=N ring double bond, the heteroaryl is optionally substituted on the ring-nitrogen atom not partaking in a C=N ring double bond by one Ci-C2alkyl (e.g. methyl), Cifluoroalkyl, methyl-C(O)- or C-ifluoroalkyl-C(O)-substituent.
More preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is a heteroaryl (in particular monocyclic heteroaryl), attached at a ring-carbon, which is optionally substituted by 1 or 2 (in particular 1) ring-carbon substituents independently being C-C2alkyl (in particular methyl), Cifluoroalkyl (in particular CF 3), 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, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is an optionally substituted monocyclic heteroaryl, attached at a ring-carbon. Such as monocyclic heteroaryl can be 5-membered or6-membered monocyclic heteroaryl.

WO 2014/191535 PCT7EP2014/061207
-31 -
More preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is an optionally substituted monocyclic heteroaryl, attached at a ring-carbon, which is:
pyridinyl (preferably pyridin-3-yl or most preferably pyridin-2-yl), pyrazolyl (preferably pyrazol-5-yl or pyrazol-4-yl, or most preferably pyrazol-3-yl), imidazolyl (preferably imidazol-2-yl), pyrazinyl, pyrimidinyl (preferably pyrimidin-4-yl), pyridazinyl (preferably pyridazin-3-yl), triazolyl (e.g. 1,2,3-triazolyl), tetrazol-5-yl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl or oxadiazolyl; optionally present (e.g. where chemically possible) as an agrochemically acceptable salt thereof (such as an agrochemically acceptable acid addition salt thereof).
Even more preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA 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), ortetrazol-5-yl; optionally present (e.g. where chemically possible) as an agrochemically acceptable salt thereof (such as an agrochemically acceptable acid addition salt thereof).
Still more preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is an optionally substituted monocyclic heteroaryl, attached at a ring-carbon, which is: pyridinyl (preferably pyridin-3-yl or most preferably pyridin-2-yl), pyrazolyl (preferably pyrazol-5-yl or pyrazol-4-yl, or most preferably pyrazol-3-yl), imidazolyl (preferably imidazol-2-yl), pyrazinyl, pyrimidinyl (preferably pyrimidin-4-yl), or pyridazinyl (preferably pyridazin-3-yl); optionally present (e.g. where chemically possible) as an agrochemically acceptable salt thereof (such as an agrochemically acceptable acid addition salt thereof).
Yet more preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA is an optionally substituted monocyclic heteroaryl, attached at a ring-carbon, which is: pyridin-3-yl, pyridin-2-yl, or pyrazolyl (preferably pyrazol-5-yl or pyrazol-4-yl, or most preferably pyrazol-3-yl); optionally present (e.g. where chemically possible) as an agrochemically acceptable salt thereof (such as an agrochemically acceptable acid addition salt thereof).
Most preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, and R39 is HetA or HetA-CH2, HetA 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

WO 2014/191535 PCT7EP2014/061207
-32-
chemically possible) as an agrochemically acceptable salt thereof (such as an agrochemically acceptable acid addition salt thereof).
It is particularly preferred (e.g. in all aspects and/or embodiments of the invention when Q is Q2 and R39 is HetA or HetA-CH2,) that, in HetA, any ring-carbon atom, which is directly bonded to the ring-carbon atom which is the point of attachment (e.g. or i.e. which is the point of attachment to the central carbon atom within the Y = CR38R39 moiety (for HetA), or which is the point of attachment to the -CH2- moiety (for Het-CH2-), is unsubstituted. Therefore, for example, preferably, when Het is an optionally substituted pyridin-2-yl (optionally present as an agrochemically acceptable salt thereof), then the ring-carbon atom at the 3-position of the ring (calculated with respect to the pyridine ring nitrogen atom) is unsubstituted.
Preferably, e.g. in all aspects and/or embodiments of the invention when Q is Q2, R310, R311, R312 and/or R313 are, independently of each other, hydrogen orC-C2alkyl (in particular hydrogen or methyl). More preferably, two, three or all of R310, R311, R312 and R313 are hydrogen. Most preferably, R310, R311, R312 and R313 are hydrogen.
In a particularly preferable embodiment of the invention (which e.g. can apply to all aspects and/or embodiments of the invention): Y is O orCR38R39 (preferably CR38R39); and R34 and R35 taken together are -(CH2)n34- or-(CH2)n35-C(R37a)(R37b)-(CH2)n36-; wherein R37a is Ci-C2alkyl; R37b is hydrogen or C-C2alkyl; n34 is 2 or 3; and n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 1 or2. In this particularly preferable embodiment, more preferably, Y is O orCR38R39 (preferably CR38R39) wherein R38 and R39 are, independently of each other, hydrogen or CrCsalkyl (in particular, this CrCsalkyl can be CrC 2alkyl such as methyl). In this particularly preferable embodiment, even more preferably Y is O orCH 2 ; or, most preferably, Y is CH 2 . In this particularly preferable embodiment, more preferably, R 33 and R36, independently of each other, are hydrogen, CrC 3alkyl (in particular CrC 2alkyl such as methyl) orCi-C3alkoxyCi-C 3alkyl (in particular Ci-C2alkoxyCrC 2alkyl); provided that no more than one (in particular none) of R33 and R36 is alkoxyalkyl. In this particularly preferable embodiment, even more preferably, R33 and R36, independently of each other, are hydrogen orCi-C2alkyl (preferably hydrogen or methyl); and/or R34 and R35 taken together are -(CH2) - wherein n34 is 2 or 3 (preferably 2).
v z'n34 vl J '

WO 2014/191535 PCT7EP2014/061207
-33-
In a further particularly preferred embodiment, R1 is fluorine, X is methyl, R2 is OR2A, wherein R2A is selected from methyl, ethyl, CH2CH2OCH 3, 2,2,2-trifluoroethyl and difluoromethyl (most preferably R2A is selected from methyl, ethyl and difluoromethyl), Q is Q2 wherein Y is CR38R39 and R38 and R39 are each independently hydrogen or methyl (preferably both hydrogen or both methyl, more preferably both hydrogen), R34 and R35 taken together are -(CH 2)n34- or-(CH2)n35-C(R 7a)(R 7 )-(CH2)n36 wherein n34, n35, n36, R 7a and R37b are as described hereinbefore. Preferably, in this particularly preferred embodiment, n34 is 2 or 3; and n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 1 or2. Preferably, in this particularly preferred embodiment, R34and R35 taken together are-(CH2)n34- wherein n34 is 2. Preferably, in this particularly preferred embodiment, G is hydrogen. In this particularly preferred embodiment, more preferably, R33 and R36, independently of each other, are hydrogen, C-C3alkyl (in particular C-C2alkyl such as methyl) or C-i-CsalkoxyC-i-Csalkyl (in particular C-C2alkoxyC-C2alkyl); provided that no more than one (in particular none) of R33 and R36 is alkoxyalkyl. In this particularly preferred embodiment, even more preferably, R33 and R36, independently of each other, are hydrogen or C-C2alkyl (preferably hydrogen or methyl); and/or R34 and R35 taken together are -(CH2)n34- wherein n34 is 2 or 3 (preferably 2).
In a specific particularly preferred embodiment, the compound of the invention (compound of formula (I)) is as described herein in the following tables (e.g. is a compound as described herein in one of Tables 1, 2, 3, 4, 5 or 6), optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
Particularly preferably, the compound of the invention (compound of formula (I)) is compound A1,A2, A3, A4, A5, A6, A7, A8, P1, P2, P3, P4 or P5, optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof. In an alternative embodiment, the compound of the invention (compound of formula (I)) is compound A9 orA10, optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
Particularly preferably, the compound of the invention (compound of formula (I)) is compound A1,A2, A3, A4, A5, A6 orA7 (more preferably compound A1, A2, A3, A4 orA7),

WO 2014/191535

PCT7EP2014/061207

34
optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
Alternatively, preferably, the compound of the invention (compound of formula (I)) is compound A8, optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
Alternatively, particularly preferably, the compound of the invention (compound of formula (I)) is compound P1, P2, P3, P4 or P5, optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
Especially particularly preferably, the compound of the invention (compound of formula (I)) is compound A1, A2, A3, A4, A7, P1, P2, P3, P4 or P5, optionally present (e.g. where chemically possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.
In an further, alternative, aspect of the invention, there is provided a compound B1, of the

following structure: , optionally present (e.g. where chemically
possible) as an agrochemically acceptable salt (e.g. agrochemically acceptable metal, sulfonium or ammonium salt) thereof.

WO 2014/191535 PCT7EP2014/061207
-35-
Processes for preparation of compounds, e.g. compounds of formula (I)
Compounds of formula I, in which Q is Q2 may in general be made by the general methods described below.
A compound of formula I, wherein Q is Q2 and G is:-C(Xa)-Ra, -C(Xb)-Xc-Rb, -C(Xd)-N(Rc)-Rd, -S0 2-Re, -P(Xe)(Rf)-R9, -CH2-Xf-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-C2alkyl, Cifluoroalkyl, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, SCrC 3alkyl, S(0)CrC 3alkyl, orS(0)2CrC 3alkyl), or heteroaryl-CH2- or heteroaryl-CH(CrC 2alkyl)- (in each of which the heteroaryl is optionally substituted by 1,2 or 3 of, independently, Ci-C2alkyl, Cifluoroalkyl, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro S, S(O), orS(0) 2), or phenyl-C(0)-CH 2 - (wherein the phenyl is optionally substituted by 1,2or3of, independently, Ci-C2alkyl, Cifluoroalkyl, Ci-C2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano, nitro, SCi-C3alkyl, S(0)Ci-C 3alkyl, or S(0) 2C|-C3alkyl); or C-|-C6alkoxy-C(0)-CH 2-, C1-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-CH2-, or C2-C7alkyn-1-yl-CH(Ci-C 2alkyl)-; may be prepared by treating a compound of formula (2A), which is a compound of formula I wherein Q is Q2 and G is H,
(a) with a reagent G1-Z, wherein G1-Z is an alkylating agent (wherein G1 is an organic group according to G within the compound of formula (I), wherein Q is Q2 and which is linked by a non-carbonyl, non-thiocarbonyl carbon atom) such as an organic halide (in which Z = halogen such as chlorine, bromine or iodine); wherein the organic halide (e.g. chloride) can typically be a substituted alkyl halide (e.g. chloride) such as a chloromethyl alkyl ether CI— CH2-Xf-Rh wherein Xf is oxygen, a chloromethyl alkyl sulfide CI—CH2-Xf-Rh wherein Xf is sulphur, a suitable optionally substituted benzyl halide (e.g. chloride) such as CI-CH2-[optionally substituted phenyl], [optionally substituted phenyl]-C(0)-CH 2-[halogen e.g. CI], C-|-C6alkoxy-C(0)-CH 2-[halogen e.g. CI], C1-C6alkoxy-C(0)-CH=CH-[halogen e.g. CI], a suitable alkenyl oralkynyl halide (e.g. chloride) such as C2-C7alken-1-yl-CH2-[halogen e.g. CI] or C2-C7alkyn-1-yl-CH2-[halogen e.g. CI], or another organic halide suitable for preparing a (non-carbonyl, non-thiocarbonyl carbon)-linked G (orG1) group; or
(b) [e.g. to prepare carbonyl-carbon-linked orthiocarbonyl-carbon-linked G groups] with an acylating agent such as a carboxylic acid, HO-C(Xa)Ra, wherein Xa is oxygen, an acid chloride, CI-C(Xa)Ra, wherein Xa is oxygen, or an acid anhydride, [RaC(Xa )]2 0 ,wherein Xa is oxygen, or an isocyanate, RcN=C=0, or a carbamoyl chloride, CI-C(Xd)-N(Rc)-Rd (wherein Xd is oxygen and with the proviso that neither Rc or Rd is hydrogen), or a thiocarbamoyi chloride

WO 2014/191535

PCT7EP2014/061207

36
CI-(Xd)-N(Rc)-Rd (wherein Xd is sulfur and with the proviso that neither Rc or Rd is hydrogen), or a chloroformate, CI-C(Xb)-Xc-Rb (wherein Xb and Xc are oxygen), or a chlorothioformate Cl-C(Xb)-Xc-Rb (wherein Xb is oxygen and Xc is sulfur), or a chlorodithioformate CI-C(Xb)-Xc-Rb (wherein Xb and Xc are sulfur), or an isothiocyanate, RCN=C=S; or
(c) by sequential treatment with carbon disulfide and an alkylating agent; or
(d) with a phosphorylating agent such as a phosphoryl chloride, CI-P(Xe)(Rf)-R9; or
(e) with a sulfonylating agent such as a sulfonyl chloride Cl-S0 2—Re, preferably in the presence of at least one equivalent (i.e. mole equivalent) of base.
Where substituent R33 is not equal to substituent R36, and/or where R34 and R35 taken together are an asymmetric chain, these reactions may produce, in addition to a compound of formula I, a second compound of formula (IAA).
This invention covers both a compound of formula (I), wherein Q is Q2, and a compound of formula (IAA), together with mixtures of these compounds in any ratio.

formula (2A)

formula I wherein Q is Q2

formula (IAA) wherein Q is Q2

The O-alkylation of cyclic 1,3-diones is known; suitable methods are described, for example, by T.Wheeler, US4436666. Alternative procedures have been reported by M. Pizzorno and S.Albonico, Chem. Ind. (London), (1972), 425-426; H. Born etal., J.Chem. Soc, (1953), 1779-1782; M. G. Constantino etal., Synth. Commun., (1992), 22 (19), 2859-2864; Y.Tian etal., Synth. Commun., (1997), 27 (9), 1577-1582; S.Chandra Roy etal., Chem. Letters, (2006), 35 (1), 16-17; P. K. Zubaidha etal., Tetrahedron Lett., (2004), 45, 7187-7188.
The O-acylation of cyclic 1,3-diones may be effected e.g. by procedures similar to those described, for example, by R. Haines, US4175135, and by T.Wheeler, US4422870, US4659372 and US4436666. Typically diones of formula (2A) may be treated with an acylating agent preferably in the presence of at least one equivalent (i.e. mole equivalent) of a suitable base, and optionally in the presence of a suitable solvent. The base may be

inorganic, such as an alkali metal carbonate or hydroxide, or a metal hydride, or an organic base such as a tertiary amine or metal alkoxide. Examples of suitable inorganic bases include sodium carbonate, sodium or potassium hydroxide, sodium hydride, and suitable organic bases include trialkylamines, such as trimethylamine and triethylamine, pyridines or other amine bases such as 1,4-diazobicyclo[2.2.2]-octane and 1,8-diazabicyclo[5.4.0]undec-7-ene. Preferred bases include triethylamine and pyridine. Suitable solvents for this reaction are selected to be compatible with the reagents and include ethers such as tetrahydrofuran and 1,2-dimethoxyethane and halogenated solvents such as dichloromethane and chloroform. Certain bases, such as pyridine and triethylamine, may be employed successfully as both base and solvent. For cases where the acylating agent is a carboxylic acid, acylation is preferably effected in the presence of a known coupling agent such as 2-chloro-1-methylpyridinium iodide, A/,A/'-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and A/,A/'-carbodiimidazole, and optionally in the presence of a base such as triethylamine or pyridine in a suitable solvent such as tetrahydrofuran, dichloromethane oracetonitrile. Suitable procedures are described, for example, by W. Zhang and G. Pugh, Tetrahedron Lett., (1999), 40 (43), 7595-7598; T. Isobe and T. Ishikawa, J. Org. Chem., (1999), 64 (19), 6984-6988 and K. Nicolaou, T. Montagnon, G. Vassilikogiannakis, C. Mathison, J.Am. Chem. Soc, (2005), 127(24), 8872-8888.
Phosphorylation of cyclic 1,3-diones may be effected e.g. using a phosphoryl halide orthiophosphoryl halide and a base e.g. by procedures analogous to those described by L. Hodakowski, US4409153.
Sulfonylation of a compound of formula (2A) may be achieved e.g. using an alkyl or aryl sulfonyl halide, preferably in the presence of at least one equivalent (i.e. mole equivalent) of base, for example by the procedure of C. Kowalski and K. Fields, J. Org. Chem., (1981 ), 46, 197-201 .
Compounds of formula (2A), wherein Y is S(O) orS(O) 2 may be prepared from compounds of formula (2A) wherein Y is S by oxidation, e.g. according to a procedure analogous to that of E. Fehnel and A. Paul, J.Am. Chem. Soc, (1955), 77, 4241-4244.
OQ Q
A compound of formula (2A), wherein Y is O, S, C(O) orCR R3 may be prepared via the cyclisation of a compound of formula (2B), preferably in the presence of an acid or base, and optionally in the presence of a suitable solvent, e.g. by analogous methods to those described by T. Wheeler, US4209532. The compounds of the formula (2B) have been particularly designed as intermediates in the synthesis of the compounds of the formula I wherein Q is Q2, and a further aspect of the present invention provides a compound of

formula (2B) (shown below). Compounds of formula (2B) wherein R is hydrogen or Cr C4alkyl, (especially methyl, ethyl and ierf-butyl) may be cyclised under acidic conditions, preferably in the presence of a strong acid such as sulfuric acid, polyphosphoric acid or Eaton's reagent, optionally in the presence of a suitable solvent such as acetic acid, toluene ordichloromethane. A compound of formula (2B) wherein R is alkyl (preferably methyl or ethyl) may also be cyclised under basic conditions in the presence of at least one equivalent (i.e. mole equivalent) of a strong base in a solvent such as tetrahydrofuran, toluene, dimethylsulfoxide or /V,/V-dimethylformamide. Suitable bases include potassium ie/f-butoxide, lithium diisopropylamide, sodium bis(trimethylsilyl)amide or sodium hydride. A compound of formula (2B), wherein R is alkyl, may be produced from a compound of formula (2B), wherein R is H, by esterification under known conditions (for example by treatment with an alcohol, R-OH, in the presence of an acid catalyst).
A compound of formula (2B), wherein R is H, may be prepared by hydrolysis of a compound of formula (2C) wherein R is H or alkyl and R' is alkyl (preferably methyl or ethyl), followed by acidification of the reaction mixture to effect decarboxylation, e.g. by similar processes to those described by, for example, T. Wheeler, US4209532. Alternatively, a compound of formula (2B), wherein R is alkyl or H may be prepared from a compound of formula (2C), wherein R' is alkyl (preferably methyl), through a Krapcho decarboxylation procedure, e.g. under known conditions using known reagents (see for example G. Quallich, P. Morrissey, Synthesis, (1993), (1), 51-53).

A compound of formula (2C) wherein R is alkyl may be prepared by treating a compound of formula (2D) with a suitable carboxylic acid chloride of formula (2E) wherein R is alkyl under basic conditions. Suitable bases include potassium ferf-butoxide, sodium bis(trimethyl-silyl)amide and lithium diisopropylamide and the reaction is preferably conducted in a suitable solvent (such as tetrahydrofuran or toluene) at a temperature between -78 °C and 30 °C. Under similar conditions a compound of formula (2C), wherein R is H, may be prepared from a suitable anhydride of formula (2F).
Compounds of formula (2E) and formula (2F) are known (see, for example T. Terasawa and T. Okada, J. Org. Chem., (1977), 42 (7), 1163-1 169; G. Bennett, W. Houlihan, R. Mason; R. Engstrom, J. Med. Chem., (1976), 19 (5), 709-14; L.J.J. Hronowski, Lucjan W. A.Szarek, Canadian Journal of Chemistry (1988), 66(1), 61-70; S. F. Birch, V. E. Gripp, D. T. McAllan, W. S. Nathan, Journal of the Chemical Society (1952), 1363-8; S. Kitamura, T. D. Aicher, Gonzales, Steve; Y. Le Huerou, S. A. Pratt, Y. Nakada, WO 200801 1130; O. Jentzer, M. Guglieri, WO 2009092795), or may be made by similar methods from commercially available starting materials.
Compounds of formula (2D), wherein X is methyl and R' is d-C4alkyl, can be prepared by reacting compounds of formula (2G) with propyne in the presence of a suitable catalyst, optionally a suitable additive, optionally in a suitable solvent at a suitable temperature. Suitable catalysts include transition metal salts or complexes of transition metal salts (for example palladium acetate, bis(triphenylphosphine) palladium(ll) dichloride, tetrakis(triphenyl-phosphine)palladium(0), bis(triphenylphosphine) nickel(ll) dichloride and tris(acetylacetonato) iron(lll)), in an amount of typically 0.001-25 mole% with respect to a compound of formula (2G). Suitable additives include copper salts, for example copper(l) iodide in an amount of typically 0.001-50 mole% with respect to a compound of formula (2G), and tetraalkyi ammonium salts. Suitable bases include diethylamine, triethylamine, piperidine

and pyrrolidine, and suitable solvents include 1,4-dioxane, A/,/V-dimethylacetamide or N,N-dimethylformamide. Preferably the reaction is carried out using 0.05-10 mole% bis(triphenylphosphine) palladium(ll) dichloride (with respect to a compound of formula (2G)), 0.05-10 mole% triphenylphosphine (with respect to a compound of formula (2G)), 0.05-25 mole% copper(l) iodide (with respect to a compound of formula (2G)), 5-200 mole% tetrabutyl ammonium iodide (with respect to a compound of formula (2G)), triethylamine and /V,/V-dimethylformamide at a temperature between 25°C to 150°C. Such a reaction is an example of a Sonogashira coupling and similar reactions are known in the literature (see for example F. Labrie, S. Gauthier, J. Cloutier, J. Mailhot, S. Potvin, S. Dion, J-Y. Sanceau, WO 2008124922; M.S.Viciu, S.P.Nolan, Modern Arylation Methods (2009), 183-220; R. Chinchilla, C. Najera, Chemical Reviews (2007), 107(3), 874-922; i. P. Beletskaya, G.V. Latyshev, A. V. Tsvetkov, N. V. Lukashev, Tetrahedron Letters (2003), 44(27), 501 1-5013 and J. Mao, G.Xie, M. Wu, J. Guo, S. Ji, Advanced Synthesis & Catalysis (2008), 350(16), 2477-2482). In an alternative approach a compound of formula (2D) may be prepared from a compound of formula (2G) by reaction with a propynyl transfer reagent such as 1-propynyllithium, 1-propynylmagnesium bromide, 1-propynylmagnesium chloride, 1-propynylmagnesium iodide, 1-propynylzinc chloride, 1-propynylzinc bromide, 1-propynylzinc iodide, tributylpropynylstannane, 1-propyne-1-boronic acid (or ester thereof), 2-butynoic acid or 1-(trimethylsilyl)propyne, with a transition metal catalyst system under suitable conditions (see for example P. Wessig, G. Mueller, C. Pick, A. Matthes, Synthesis (2007), (3), 464-477; J. H. Chaplin, G.S.Gill, D. W. Grobelny, B. L. Flynn, G. Kremmidiotis, WO07087684; A. Akao, T.Tsuritani, S. Kii, K. Sato, N. Nonoyama, T. Mase, N. Yasuda, Synlett (2007), (1), 31-36. A. Coelho Coton, E. Sotelo Perez, F. Guitian Rivera, A. Gil Gonzalez, WO 201 1048247; C. H. Oh, S. H.Jung, Tetrahedron Letters (2000), 41(44), 8513-8516; D.Zhao, C. Gao, X. Su, Y. He, J. You, Y.Xue, Chemical Communications (2010), 46(47), 9049-9051 ; C.Yang, S. P. Nolan, Organometallics (2002), 21(6), 1020-1022). in another set of preferred conditions a compound of formula (2G) is reacted with 1-propynylmagnesium bromide in the presence of 0.05-10 mole% bis(triphenylphosphine) palladium(ll) dichloride (with respect to a compound of formula (2G)), in tetrahydrofuran at a temperature between 25°C and 100°C, as described by J. H. Chaplin, G. S. Gill, D. W. Grobelny, B. L. Flynn, G. Kremmidiotis, WO 07087684. Compounds of formula (2G) are known, or can be prepared by known methods using known reagents.

Compounds of formula (2D), wherein X is chlorine and R' is CrC 4alkyl, can be prepared from compounds of formula (2H) or compounds of formula (21). in one approach a compound of formula (2H) is first deprotonated with a base such as butyllithium, sodium hydride, lithium diisopropylamide orethylmagnesium bromide, then reacted with a chlorine source such as /V-chloro succinimide, chlorine or carbon tetrachloride. The specific chlorine source is selected to provide the required chloro-acetylene. Similar reactions and conditions are reported in the literature (see for example M. Tajbakhsh, S. Habibzadeh, Letters in Organic Chemistry (2007), 4(7), 512-514; D. Sud, T. J. Wigglesworth, N. R. Branda, Angewandte Chemie, International Edition (2007), 46(42), 8017-8019; M.A. P. Martins, D.J. Emmerich, C. M. P. Pereira, W. Cunico, M. Rossato, N. Zanatta, H. G. Bonacorso, Tetrahedron Letters (2004), 45(25), 4935-4938; A. Poloukhtine, V. Rassadin, A. Kuzmin, V. V. Popik, Journal of Organic Chemistry (2010), 75(17), 5953-5962; C. R. Hickenboth, J. D. Rule, J. S. Moore, Tetrahedron (2008), 64(36), 8435-8448; F. H. M. Graichen, A. C. Warden, S. Kyi, M. S. O'Shea, Australian Journal of Chemistry (2010), 63(4), 719-722; and M. L. Narayana, M. L. N. Rao, M. Periasamy, Synthetic Communications (1995), 25(15), 2295-9).
in another approach a compound of formula (2D), wherein X is chlorine and R' is d -C4alkyl, can be prepared from a compound of formula (2H) by treatment with a mixture of reagents that are known to promote chlorination, such as potassium carbonate, tetrabutylammonium bromide and carbon tetrachloride (see for example T. Matsuda, S. Kadowaki, Y.Yamaguchi, M.Murakami, Chemical Communications (2008), (24), 2744-2746), pyridine and chlorine (see for example R. B. Gutsulyak, V. N. Britsuk, L. A. Kostrikina, Y.Serguchev, Ukrainskii Khimicheskii Zhurnal (1993), 59(10), 1062-7), silver nitrate and N-chloro succinimide, N-chloro succinimide and hexamethylphosphoramide (see for example G. Pangon, J. L. Philippe, P. Cadiot, Comptes Rendus des Seances de I'Academie des Sciences, Serie C: Sciences Chimiques (1973), 277(18), 879-81 ), and/or perchloric acid and acetic acid (see for example J. P. Montheard, M. Camps, M. Chatzopoulos, M. O. A. Yahia, R. Guilluy, D. Deruaz, Journal of Chemical Research, Synopses (1983), (9), 224-5). Conditions are selected to provide the required chloro-

acetylene. When X is chlorine, preferred conditions include reacting a compound of formula (2H) with 1-5 mole equivalents of N-chloro succinimide and 0.05-50 mole% silver acetate (with respect to a compound of formula (2H)) in acetone at a temperature between 25°C and 100°C.
Compounds of formula (21), wherein R' is d-C 4alkyl and R' is CrC4alkyl, can also be directly converted to compounds of formula (2D), e.g. by treatment with isocyanuric chloride or N-chloro succinimide and silver nitrate (see for example M. H. Vilhelmsen, A. S. Andersson, M B. Nielsen, Synthesis (2009), (9), 1469-1472).
A compound of formula (21), wherein R' is CrC4alkyl and R' is CrC4alkyl, can be prepared by reacting a compound of formula (2G) with a trialkylsilylacetylene, under similar conditions described previously to convert a compound of formula (2G) to a compound of formula (2D) (wherein X is methyl).
A compound of formula (2H) can either be prepared by deprotection of a compound of formula (21) under known conditions, or by reacting a compound of formula (2G) with an ethynyl transfer reagent such as tributylstannylacetylene, lithium acetylide ethylenediamine complex, ethynylzinc bromide orethynylmagnesium chloride in the presence of a suitable catalyst system, e.g. under conditions similar to those described previously (see for example C. Fischer, J. Methot, H. Zhou, A. J. Schell, B. Munoz, A. A. Rivkin, S. P. Ahearn, S. Chichetti, R.N. Maccoss, S. D. Kattar, M. Christopher, C. Li, A. Rosenau, W. C. Brown, WO 2010071741 ; M. Behler, A. Eluntlaut, C. Ferman, A. Chapuf, CN 101 195641 ; G.Wang, G. Zhu, E. Negishi, Journal of Organometallic Chemistry (2007), 692(21 ), 4731-4736 and E. Negishi, M. Kotora, C.Xu, Journal of Organic Chemistry (1997), 62(25), 8957-8960).

in a further approach, a compound of formula (2D) (wherein X is chlorine) can either be prepared from a compound of formula (2J) or a compound of formula (2K), by treatment with a suitable base, in a suitable solvent, at a suitable temperature. A compound of formula (2J) can be converted to a compound of formula (2D) under conditions similar to those described in the literature, for example treatment using potassium fe/f-butoxide in tert-butanol at a temperature between 25°C and 150°C, or lithium 2,2,6,6-tetramethylpiperidine in tetrahydrofuran at a temperature between -25°C and 50°C (see for example E. Bartmann, R. Hittich, H. Plach, U. Finkenzeller, US5188759 and Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1978, vol. 16, 1051-1054). A compound of formula (2K) can also be converted to a compound of formula (2D) under conditions similar to those described in the literature, for example by treatment with cesium carbonate in N,N-dimethylformamide at a temperature between 25°C and 150°C, sodium ie/f-butoxide in toluene at a temperature between 25°C and 150°C, 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylsulfoxide at a temperature between 0°C and 50°C, or potassium ie/f-butoxide in tetrahydrofuran at a temperature between -78°C and 25°C (see for example B. C. G. Soederberg, S. P. Gorugantula, C. R. Howerton, J. L. Petersen, S. W. Dantale, Tetrahedron (2009), 65(36), 7357-7363; S-C. Lo, R. E. Harding, E. Brightman, P. L. Burn, i. D. W. Samuel, Journal of Materials Chemistry (2009). 19(20), 3213-3227; S.Wang, T. Kohn, Z. Fu, X.Y. Jiao, S. Lai, M. Schmitt, Tetrahedron Letters (2008), 49(51 ), 7284-7286 and M. L. G. Borst, R. E. Bulo, D.J. Gibney, Y. Alem, F.J.J, de Kanter, A. W. Ehlers, M. Schakel, M. Lutz, A. L. Spek, K. Lammertsma, Journal of the American Chemical Society (2005), 127(48), 16985-16999). Compounds of formula (2J) and (2K) (wherein X is chlorine) can be prepared from known compounds using known methods and reagents.

in a further approach a compound of formula (2A), wherein X is methyl, can be prepared directly from a compound of formula (2L), under similar conditions described previously to convert a compound of formula (2G) to a compound of formula (2D).
A compound of formula (2L) can be prepared from a compound of formula (2G) using similar procedures to those outlined previously.

A compound of formula (2A), wherein X is chlorine, can be prepared from a compound of formula (2L), via either a compound of formula (20) or a compound of formula (2P) (wherein R' is CrC 4alkyl), e.g. under similar conditions to those described previously.

A compound of formula (2A), wherein X is chlorine, can also be prepared from a compound of formula (2Q), e.g. under conditions similar to those described for converting a compound of formula (2K) to a compound of formula (2D).
A compound of formula (2Q), wherein X is chlorine may be prepared from an aldehyde of formula (2R) by treatment with triphenylphosphine in the presence of carbon tetrachloride in a suitable solvent at a suitable temperature. Carbon tetrachloride is selected to provide the required dichloroalkene, and similar reactions are known in the literature (see for example A. Poloukhtine, V.V. Popik, Journal of the American Chemical Society (2007), 129(40), 12062-12063; L. N. Michaelides, B. Darses, D.J. Dixon, Organic Letters (201 1), 13(4), 664-667 and F. Gavina, S.V. Luis, P. Ferrer, A. M. Costero, J. A. Marco, Journal of Chemical Research, Synopses (1986), (9), 330-1).
A compound of formula (2R) may be prepared by the formylation of a compound of formula (2L) (wherein Hal is chlorine, bromine or iodine, preferably bromine or iodine). Suitable conditions for effecting the formylation of aryl halides are known, and include, for example, the treatment of an aryl halide with a suitable organometallic reagent, such as isopropyl magnesium chloride, n-butyllithium, sec-butyllithium or ie/f-butyllithium, or by treatment with a suitable alkali metal or alkali earth metal such as lithium or magnesium in a suitable solvent, such as diethyl ether, dimethoxyethane or tetrahydrofuran. The resulting arylmetal reagent is then reacted with a suitable formylating agent such as N,N-

dimethylformamide or /V-formylmorpholine. Alternatively a compound of formula (2R) may be prepared from a compound of formula (2L) (wherein Hal can also be a pseudohalogen such as triflate) by treatment with a carbonylating agent (such as carbon monoxide in the presence of a suitable catalyst system, base, and reducing agent (see for example L. Ashfield and C. Barnard, Org. Process Res. Dev., 11 (1), 39-43, 2007).
in an alternative approach, a compound of formula i, wherein Q is Q2, X is methyl, and wherein G is preferably substituted alkyl (e.g. optionally substituted phenyl-CH2- or heteroaryl-CH 2-), or hydrogen, or methyl or ethyl (the latter two are not within formula I but can be converted to G = H later), may be prepared from a boronic acid or boronic ester of formula (2S) by treatment with either 1-bromo-1-propyne or 1-iodo-1-propyne, preferably in the presence of a suitable catalyst system, a suitable base and/or a suitable solvent and/or at a suitable temperature. Similar reactions are known in the literature, and preferred conditions involve reacting a compound of formula (2S) with 1-iodo-propyne in the presence of 0.005-25 mole% palladium(ll) chloride (with respect to a compound of formula (2S)) and 1-10 equivalents (i.e. mole equivalents) of potassium carbonate, preferably in a mixture of toluene, water and methanol at a temperature between 50°C-150°C, as described by Y.Shi, X. Li, J. Liu, W. Jiang, L. Sun, Tetrahedron Letters (2010), 51(28), 3626-3628. A compound of formula (2T), wherein G is preferably methyl or ethyl and R" is CrC 4alkyl, may be prepared under similar conditions using either 1-bromo-2-(trimethylsilyl)acetylene or 1-iodo-2-(trimethylsilyl)acetylene as the coupling partner. Compounds of formula (2A) and (2P) may be prepared from compounds of formula i, wherein Q is Q2, and (2T) respectively, by hydrolysis of the enol ether.

CLAIMS
A compound of formula (I)
wherein:
X is methyl or chlorine;
R1 is fluorine or bromine;
R2 is ethynyl, C-i-C3alkoxy-, C-i-C3haloalkoxy-, or d-dalkoxy-d-dalkoxy-; and
Q is a group of formula Q2:
wherein in Q2:
R33 and R36, independently of each other, are hydrogen, Ci-C5alkyl, C2-C4alkenyl, C2-
C4alkynyl, CpC^luoroalkyl, d-dalkoxyd-dalkyl, d-dalkylthiod-dalkyl, Cr
dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl, C3-C4cycloalkyl, or an
unsubstituted 4, 5 or6 membered monocyclic heterocydyl having one ring heteroatom
independently selected from oxygen, sulfur and nitrogen, said heterocydyl being
attached at a ring carbon atom within the heterocydyl ;
provided that no more than one of R33 and R36 is alkenyl, alkynyl, alkoxyalkyl,
alkylthioalkyi, alkylsulfinylalkyi, alkylsulfonylalkyi, cycloalkyi or heterocydyl; and

R34 and R35 taken together are -(CH2)n34- or-(CH2)n35-C(R37a)(R37b)-(CH2)n36-;
wherein R37a is CrC2alkyl; R37b is hydrogen or CrC2alkyl;
n34 is 1,2 or 3; and
n35 and n36 are independently 0, 1 or2 provided that n35 + n36 is 0, 1 or2; and
Y is O, S, S(O), S(0) 2, N(CrC 2alkyl), N(d-dalkoxy), C(O), CR38R39or-
c R 310 R 311c R 312 R 313_. gnc|
R38 and R39 are, independently of each other: hydrogen, d-dalkyl, C2-C4alkenyl, C2-
C4alkynyl, CrC2fluoroalkyl, Ci-C3alkoxyCi-C 3alkyl, Ci-C3alkylthioCi-C 3alkyl, Cr
dalkylsulfinyld-dalkyl, or d-dalkylsulfonyld-dalkyl; C3-C6cycloalkyl orC3-
C6cycloalkyl substituted by one or two substituents which independently are CrC3alkyl
or C-i-C2fluoroalkyl, and in which one ring CH2 moiety of a C4-C6cycloalkyl is optionally
replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(C-|-C3alkyl), N(Cr
C2fluoroalkyl), N[C(0)C rC3alkyl], N[C(0)C rC2fluoroalkyl] or N(CrC2alkoxy) moiety;
C3-C6cycloalkyl substituted by one substituent being C-i-C3alkoxy and optionally further
substituted by one substituent being d-dalkyl; d-dcycloalkenyl or d-dcycloalkenyl
substituted by one or two d-dalkyl substituents; d-dcycloalkyld-dalkyl- °rC3-
dcycloalkyld-dalkyl- substituted by one or two ring substituents which independently
are d-dalkyl ord-C 2fluoroalkyl, and in which one ring CH2 moiety of a
d-dcycloalkyld-dalkyl- is optionally replaced by an oxygen or sulfur atom or by a
S(O), S(0) 2, NH, N(d-dalkyl), N(Ci-C2fluoroalkyl), N[C(0)d-dalkyl], N[C(0)d-dfluoroalkyl] or N(C-|-C2alkoxy) moiety; d-dcycloalkyld-dalkyl- substituted by one ring substituent being d-dalkoxy and optionally further substituted by one ring substituent being d-dalkyl; 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 d-dalkyl, d-C 2fluoroalkyl, d-dalkyl-C(O)-, d-dfluoroalkyl-C(O)-, -C(0)-N(R eH)(R6j), SR6E, S(0)R 6E, -S(0) 2-R6E, -N(R6F)(R6G), hydroxy, d-dalkenyl, -C(R6BB)=C(R6c1)(R6C2), C2-dalkynyl, -OC-R6^, d-dalkoxy, d-C2fluoroalkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HC=C-CH2-0-, halogen, cyano ornitro; 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-C3alkyl, Ci-C2fluoroalkyl, CrC3alkyl-C(0)-, d-C2fluoroalkyl-C(0)- or Ci-C2alkyl-S(0) 2- substituent;
provided that no more than one of R38 and R39 is an optionally substituted cycloalkyi, an optionally substituted cycloalkyi in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(CrC3alkyl), N(CrC2fluoroalkyl), N[C(0 )CrC3alkyl], N[C(0)C rC2fluoroalkyl] or N(CrC2alkoxy) moiety; an optionally substituted cycloalkenyl, an optionally substituted cycloalkyl-alkyl-, an optionally substituted cycloalkyl-alkyl- in which one ring CH2 moiety has been replaced by an oxygen or sulfur atom or by a S(O), S(0) 2, NH, N(CrC3alkyl), N(CrC2fluoroalkyl), N[C(0)C 1-C3alkyl], N[C(0)C rC2fluoroalkyl] or N(CrC2alkoxy) moiety, or HetA or HetA-CH2-;
or R38 is hydrogen orCrC2alkyl, and R39 is CrC2alkoxy;
or R38 and R39 taken together are -(CH2)n37- or-(CH2)n38-X32-(CH2)n3g-;
wherein X32 is O, S, S(O), S(0) 2, NH, N(CrC3alkyl), N(CrC2fluoroalkyl),
N[C(0 )CrC3alkyl], N[C(0)C rC2fluoroalkyl], N(CrC2alkoxy), C(H)(CrC3alkyl),
C(Ci-C2alkyl)2 or C(H)(CrC3alkoxy);
n37 is 2, 3, 4, 5 or6; and
n38 and n39 are independently 0, 1,2 or 3 provided that n38 + n39 is 2, 3, 4 or 5; and
R31°, R311, R312 and R313 are independently of each other hydrogen or CrC4alkyl provided that no more than one of R31°, R311, R312 and R313 is C3-C4alkyl;
and wherein:
R6^ is Cifluoroalkyl, fluorine, chlorine or bromine;
R6BB peel anc| R6C2 independently are hydrogen, methyl, Cifluoroalkyl, fluorine or
chlorine; provided that R6BB, R6c1 and R6C2 in total contain no more than one carbon
atom, and R6BB, R6c1 and R6C2 in total comprise no more than one chlorine; and
provided that -C(R6BB)=C(R6c1)(R6C2) is not C2-C3alkenyl;
R6E is CrC3alkyl, Cifluoroalkyl, or-N(R6H)(R6j);
R6F is -C(0 )-CrC2alkyl, -C(0)-Cifluoroalkyl, -S(0) 2-CrC2alkyl, -S(0) 2-Cifluoroalkyl,
Ci-C2alkyl, or Cifluoroalkyl;

R and R independently are hydrogen, methyl or C-ifluoroalkyl; RsH is hydrogen, CrC2alkyl, or Cifluoroalkyl;
and wherein:
G is hydrogen, an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group; or
G is -C(Xa)-Ra, -C(Xb)-Xc-Rb, -C(Xd)-N(Rc)-Rd, -SO 2-Re, -P(Xe)(Rf)-R9, -CH2-Xf-Rh; or phenyl-CH2- or phenyl-CH(CrC 2alkyl)- (in each of which the phenyl is optionally substituted by 1,2 or 3 of, independently, Ci-C2alkyl, Cifluoroalkyl, Ci-C2alkoxy, C-ifluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or heteroaryl-CH2- or heteroaryl-CH(CrC2alkyl)- (in each of which the heteroaryl is optionally substituted by 1,2 or 3 of, independently, C-|-C2alkyl, dfluoroalkyl, d-C 2alkoxy, dfluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or phenyl-C(0)-CH 2- (wherein the phenyl is optionally substituted by 1,2or3of, independently, Ci-C2alkyl, Cifluoroalkyl, d -C2alkoxy, dfluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro); or Ci-C6alkoxy-C(0)-CH2-, d-C 6alkoxy-C(0)-CH=CH-, C2-C7alken-1-yl-CH2-, C2-Cyalken-1-yl-CH(CrC2alkyl)-, C2-C4fluoroalken-1-yl-CH 2-, C2-C7alkyn-1-yl-CH2-, or C2-Cyalkyn-1-yl-CH(CrC 2alkyl)-;
Xa, Xb, Xc, Xd, Xe and Xf are independently of each other oxygen or sulfur;
Rais H, CfC2ialkyl, C2-C2ialkenyl, C2-C18alkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d-C 10nitroalkyl, d-C 10aminoalkyl, CpCgalkylamino^-C^alkyl, C2-C8dialkylamino(d-C5)alkyl, c3-C7cycloalkyl(d-C 5)alkyl, CfC5alkoxy(C1-C5)alkyl, C3-C5alkenyloxy(d-C5)alkyl, c3-C5alkynyloxy(d-C5)alkyl, C1-C5alkylthio(CfC5)alkyl, d-dalkylsulfinyKd-C5)alkyl, CpCgalkylsulfonyKCpC^alkyl, C2-C8alkylideneaminoxy(C ^C^alkyl, Cr C5alkylcarbonyl(d-C5)alkyl, C^CgalkoxycarbonyKC ^C^alkyl, aminocarbonyl(d-C5)alkyl, Ci-C5alkylaminocarbonyl(Ci-C 5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C 5)alkyl, Ci-C5alkylcarbonylamino(Ci-C 5)alkyl, A/-(Ci-C5)alkylcarbonyl-/V-(Ci-C5)alkylamino(Ci-C5)alkyl, c3-C6trialkylsilyl(Ci-C 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 -C3alkoxy, Ci-C3fluoroalkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(Ci-C 5)alkyl (wherein the heteroaryl is optionally substituted by 1,2or3of, independently, Ci-C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, d -

Cgfluoroalkoxy, CrCsalkylthio, d-C 3alkylsulfinyl, d-C 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, d-C3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; orheteroaryl orheteroaryl substituted by 1,2 or 3 of, independently, d -C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro;
Rb is CrCi 8alkyl, C3-Ci8alkenyl, C3-Ci8alkynyl, C2-Ci0fluoroalkyl, Ci-Ciocyanoalkyl, d -ClQnitroalkyl, C2-Ci0aminoalkyl, Ci-C5alkylamino(Ci-C 5)alkyl, C2-C8dialkylamino(Cr C5)alkyl, C3-C7cycloalkyl(Ci-C 5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Cr C5)alkyl, C3-C5alkynyloxy(Ci-C 5)alkyl, Ci-C5alkylthio(Ci-C 5)alkyl, Ci-C5alkylsulfinyl(Cr C5)alkyl, CpCgalkylsulfonyKCpC^alkyl, C2-C8alkylideneaminoxy(C ^C^alkyl, d -C5alkylcarbonyl(C ^C^alkyl, C^CgalkoxycarbonyKC ^C^alkyl, aminocarbonyl(Cr C5)alkyl, CpCgalkylaminocarbonyKC ^C^alkyl, C2-C8dialkylaminocarbonyl(C ^C^alkyl, CrCgalkylcarbonylamino^rC^alkyl, /V-tC-i-C^alkylcarbonyl-A/^C-i-C^alkylamino^r C5)alkyl, C3-C6trialkylsilyl(CrC5)alkyl, phenyl(CrC5)alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, Ci-Csalkoxy, CrCsfluoroalkoxy, CrC 3alkylthio, CrC 3alkylsulfinyl, d-C 3alkylsulfonyl, halogen, cyano, or nitro), heteroarylCi-C 5alkyl (wherein the heteroaryl is optionally substituted by 1,2or3of, independently, Ci-C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, d -C3fluoroalkoxy, CrC 3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or nitro), C3-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; orheteroaryl orheteroaryl substituted by 1,2 or 3 of, independently, d -C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, CrC 3fluoroalkoxy, halogen, cyano or nitro; and
Rc and Rd are each independently of each other hydrogen, CrC i0alkyl, C3-C1oalkenyl, C3-C10alkynyl, C2-C10fluoroalkyl, d-C 10cyanoalkyl, d-C 10nitroalkyl, CrC 10aminoalkyl, Ci-C5alkylamino(CrC5)alkyl, C2-C8dialkylamino(CrC 5)alkyl, C3-C7cycloalkyl(d-C5)alkyl, Ci-C5alkoxy(CrC5)alkyl, C3-C5alkenyloxy(CrC 5)alkyl, C3-C5alkynyloxy(Cr C5)alkyl, Ci-C5alkylthio(CrC5)alkyl, CfC5alkylsulfinyl(C1-C5)alkyl, CrC 5alkylsulfonyl(Cr C5)alkyl, C2-C8alkylideneaminoxy(CrC 5)alkyl, Ci-C5alkylcarbonyl(CrC5)alkyl, d -C5alkoxycarbonyl(CrC 5)alkyl, aminocarbonyl(CrC 5)alkyl, CrC 5alkylaminocarbonyl(Cr C5)alkyl, C2-C8dialkylaminocarbonyl(CrC 5)alkyl, Ci-C5alkylcarbonylamino(CrC5)alkyl, /V-(CrC5)alkylcarbonyl-/V-(C2.C5 )alkylaminoalkyl, C3-C6trialkylsilyl(CrC 5)alkyl,

phenyl(C-i-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-C3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, CrC 3fluoroalkoxy, d -C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, ornitro), heteroaryl(CrC 5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, d -C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, ornitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano ornitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, d -C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1,2 or 3 of, independently, d -C3alkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; diheteroarylamino ordiheteroarylamino substituted by 1,2 or 3 of, independently, d -dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1,2 or 3 of, independently, d-dalkyl, d -dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by 1,2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; or C3-dcycloalkylamino, di(C3-C7cycloalkyl)amino or C3-C7cycloalkoxy; or Rc and Rd, 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 orS; and
Re is d-C 10alkyl, C2-C10alkenyl, C2-C10alkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d -C10nitroalkyl, CrC 10aminoalkyl, CrC 5alkylamino(CrC 5)alkyl, C2-C8dialkylamino(Cr d)alkyl, C3-C7cycloalkyl(CrC 5)alkyl, CrC 5alkoxy(CrC 5)alkyl, C3-C5alkenyloxy(d-C5)alkyl, C3-C5alkynyloxy(CrC 5)alkyl, CrC 5alkylthio(CrC 5)alkyl, CrC 5alkylsulfinyl(Cr C5)alkyl, Ci-C5alkylsulfonyl(CrC 5)alkyl, C2-C8alkylideneaminoxy(CrC 5)alkyl, d -C5alkylcarbonyl(CrC 5)alkyl, Ci-C5alkoxycarbonyl(CrC 5)alkyl, aminocarbonyl(d-C5)alkyl, Ci-C5alkylaminocarbonyl(CrC 5)alkyl, C2-C8dialkylaminocarbonyl(CrC 5)alkyl, Ci-C5alkylcarbonylamino(CrC 5)alkyl, /V-(Ci-C5)alkylcarbonyl-/V-(CrC 5)alkylamino(Cr C5)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 -dalkoxy, Ci-C3fluoroalkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl,

halogen, cyano, or nitro), heteroaryl(CrC5)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, CrC 3alkyl, CrC 3fluoroalkyl, CrC 3alkoxy, d -C3fluoroalkoxy, Ci-C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, d -C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1,2 or 3 of, independently, d -C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino ordiheteroarylamino substituted by 1,2 or 3 of, independently, d -C3alkyl, 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, d-C 3alkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; diphenylamino ordiphenylamino substituted by 1,2 or 3 of, independently, d-C 3alkyl, d -dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; or C3-dcycloalkylamino, di(d-dcycloalkyl)amino, d-dcycloalkoxy, d-d Oalkoxy, d -Cofluoroalkoxy, d-dalkylamino or di(d-dalkyl)amino;
Rf and R9 are independently of each other d-d 0alkyl, C2-d 0alkenyl, d-Ci 0alkynyl, d -
C10alkoxy, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d-C 10nitroalkyl, d-C 10aminoalkyl, d -
dalkylamino(C 1-d)alkyl, d-ddialkylamino(C 1-d)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl,
C1-dalkoxy(C 1-d)alkyl, d-dalkenyloxy(d-d)alkyl, d-dalkynyloxy(d-d)alkyl, Cr
dalkylthio(d-d)alkyl, C1-dalkylsulfinyl(C fC5)alkyl, Cfdalkylsulfonyl(C fd)alkyl, C2-
dalkylideneaminoxy(C 1-d)alkyl, C|-dalkylcarbonyl(C ^C^alkyl, d -
dalkoxycarbonyl(C rd)alkyl, aminocarbonyl(Crd)alkyl, d-C 5alkylaminocarbonyl(d-
d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, C.|-dalkylcarbonylamino(C 1-d)alkyl,
/V-(d-d)alkylcarbonyl-/V-(d-d)alkylaminoalkyl, C3-C6trialkylsilyl(d-C 5)alkyl, phenyl(Crd)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, d -C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, Crdfluoroalkoxy, d -C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of,

independently, C1-C3alkyl, d-C 3fluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, 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 ordiheteroarylamino 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, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; diphenylamino ordiphenylamino substituted by 1,2 or 3 of, independently, d-dalkyl, d -dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; or C3-dcycloalkylamino, di(d-dcycloalkyl)amino, C3-dcycloalkoxy, d-C 10fluoroalkoxy, d -dalkylamino or di(d-dalkyl)amino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by 1, 2 or 3 of, independently, d -dalkyl, d-dfluoroalkyl, d-dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; and
Rh is d-d 0alkyl, C3-d 0alkenyl, d-Ci 0alkynyl, d-C 10fluoroalkyl, d-C 10cyanoalkyl, d -ClQnitroalkyl, d-Ci Oaminoalkyl, d-dalkylamino(Ci-d)alkyl, d-ddialkylamino(Ci-d)alkyl, d-dcycloalkyl(d-d)alkyl, Ci-dalkoxy(d-d)alkyl, d-dalkenyloxy(C r d)alkyl, d-dalkynyloxy(d-d)alkyl, C1-dalkylthio(C 1-d)alkyl, d-dalkylsulfinyKd-d)alkyl, C|-dalkylsulfonyl(C ^C^alkyl, d-dalkylideneaminoxy(C 1-d)alkyl, d -dalkylcarbonyl(d-d)alkyl, C|-dalkoxycarbonyl(C 1-d)alkyl, aminocarbonyl(d-d)alkyl, C^dalkylaminocarbonyKC 1-d)alkyl, d-ddialkylaminocarbonyl(d-d)alkyl, C.|-dalkylcarbonylamino(C 1-d)alkyl, A/-(C1-d)alkylcarbonyl-/V-(C 1-d)alkylamino(C 1-d)alkyl, d-dtrialkylsilyl(C rd)alkyl, phenyl(Crd)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d -dalkoxy, Crdfluoroalkoxy, d-C 3alkylthio, d-C 3alkylsulfinyl, d-C 3alkylsulfonyl, halogen, cyano or nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, Ci-C3alkoxy, d -C3fluoroalkoxy, d-C 3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano or nitro), phenoxy(CrC ^alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, d-C 3alkyl, d-C 3fluoroalkyl, Ci-C3alkoxy, Crdfluoroalkoxy, d -C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano or nitro), heteroaryloxy(CrC 5)alkyl (wherein the heteroaryl is optionally substituted by 1,2 or 3

of, independently, CrC3alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, Cr C3alkylthio, CrC 3alkylsulfinyl, CrC 3alkylsulfonyl, halogen, cyano ornitro), C3-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, CrC 3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano ornitro; heteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, d -C3alkyl, d-C 3fluoroalkyl, d-C 3alkoxy, d-dfluoroalkoxy, halogen, cyano ornitro; d-C 6alkyl-C(0)-; or phenyl-C(O)- wherein the phenyl is optionally substituted by 1 or 2 of, independently, d-dalkyl, dfluoroalkyl, d-C 2alkoxy, Cifluoroalkoxy, fluorine, chlorine, bromine, cyano ornitro;
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 R1 is fluorine.
4. A compound according to claim 1 or claim 2, wherein R1 is bromine.

5. A compound according to claim 1,2,3 or4, wherein R2 is -0-R 2A, and wherein R2A is methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl, or-CH2CH2OCI-l3.
6. A compound according to claim 1, 2 or 3, wherein R2 is -0-R 2A, and wherein R2A is methyl, ethyl, trifluoromethyl or difluoromethyl.
7. A compound according to claim 1, 2 or 3, wherein R2 is -0-R 2A, and wherein R2A is methyl.
8. A compound according to claim 6 or 7, wherein R1 is fluorine and X is methyl.
9. 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; orG is -C(Xa)-Ra or-C(Xb)-Xc-Rb.
10. A compound according to claim 9, wherein:
Xa and Xb are oxygen, and Xc is oxygen or sulfur;
Rais Ci-Ci 0alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, Ci-C4alkoxyCi-C4alkyl, C3-C7cycloalkylCialkyl; or phenyl or phenyl substituted by 1,2 or 3 of, independently, CrC 3alkyl, CrC3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; orheteroaryl or heteroaryl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, Cr C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, or cyano; and Rb is Ci-doalkyl, C2-C5alkenyl-CH2- , C2-C4alkenyl-CH(Me)-, C2-C5alkynyl-CH2-, C2-C4alkynyl-CH(Me)-, C3-C6cycloalkyl, Ci-C4alkoxyCrC4alkyl, C3-C7cycloalkylCialkyl; or phenyl or phenyl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, Ci-C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, cyano or nitro; orheteroaryl orheteroaryl substituted by 1,2 or 3 of, independently, Ci-C3alkyl, Cr C3fluoroalkyl, Ci-C3alkoxy, Ci-C3fluoroalkoxy, halogen, or cyano.
11. A compound according to any one of claims 1 to 10, wherein R33 and R36,
independently of each other, are hydrogen, CrC3alkyl or C-i-CjalkoxyC-i-Cjalkyl;
provided that no more than one of R33 and R3(3 is alkoxyalkyl;
and R34 and R35 taken together are -(CH2)n34- or-(CH2)n35-C(R37a)(R37b)-(CH2)n36-;
wherein R3?a is CrC2alkyl; R37b is hydrogen or CrC2alkyl;
n34 is 2 or 3; and
n35 and n36 are independently 0, 1 or 2 provided that n35 + n36 is 1 or 2.
12. The compound according to any one of claims 1 to 10 or 11, wherein
R33 and R36, independently of each other, are hydrogen or Ci-C2alkyl; and R34 and R35 taken together are -(CH2)n34- wherein n34 is 2 or 3.
13. The compound according to any one of claims 1 to 10, 11 or 12, wherein R38 and R39, independently of each other, are hydrogen or Ci-C3alkyl.
14. A compound according to any one of claims 1 to 10, or 11 to 13, wherein Y is O or CR38R39.

15. A compound according to any one of claims 1 to 10, or 11 to 13, wherein
Y is CR38R39; and
R34 and R35 taken together are -(CH2)n34- or-(CH2)n35-C(R37a)(R37b)-(CH2)n36-;
wherein R3?a is CrC2alkyl; R37b is hydrogen or CrC2alkyl;
n34 is 2 or 3; and
n35 and n36 are independently 0, 1 or 2 provided that n35 + n36 is 1 or 2.
16. A compound according to any one of claims 1 to 10, or 11 to 15, wherein Y is CH2.
17. A compound according to claim 15 or 16, wherein
R33 and R36, independently of each other, are hydrogen or GrC2alkyl; and R34 and R35 taken together are -(CH2)n34-wherein n34 is 2 or 3.
18. A compound according to claim 1, 7, 9, 10, 11, 12, 15, 16 or 17, wherein:
R1 is fluorine,
X is methyl,
R2 is OR2A, wherein R2A is selected from methyl, ethyl and difluoromethyl,
and Q is Q2 wherein:
Y is CR3sR39, and R38 and R39 are each independently hydrogen or methyl, and
R34 and R35 taken together are -(CH 2)n34- or-(CH2)n35-C(R37a)(R37b)-(CH2)n36 wherein n34, n35, n36, R37a and R37b are as defined in claim 1, 11, 12, 15 or 17.
19. A compound according to any preceding claim, which is compound A1, A2, A3, A4, A5,
A6, A7, A8, P1, P2, P3, P4 or P5:

in each case optionally present as an agrochemically acceptable salt thereof.
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.
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, ora herbicidal composition according to claim 20, to the weeds and/or to the plants and/or to the locus thereof.
A method as claimed in claim 2 1, wherein the crops of useful plants comprise wheat, barley, rye, triticale, sugarcane, soybean, peanut, pulse crops, cotton, rape, sunflower, linseed, sugarbeet, fodder beet, potato, and/or dicotyledonous vegetables.