(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT)
`(19) World Intellectual Property
`Organization
`International Bureau
`
`(OQ UTAATTA AYA
`
`(43) International Publication Date
`30 December 2015 (30.12.2015)
`
`WIPO!IPCT
`
`\=
`
`(10) International Publication Number
`WO 2015/197468 Al
`
`Designated States (unless otherwise indicated, for every
`kind of national protection available): AE, AG, AL, AM,
`AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY,
`BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM,
`DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT,
`HIN, HR, HU,ID,IL, IN, IR, IS, JP, KE, KG, KN, KP, KR,
`KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG,
`Mk, MN, MW,MX, MY, MZ, NA, NG, NI NO, NZ, OM,
`PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC,
`SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN,
`TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW.
`
`GD)
`
`International Patent Classification:
`C07D 309/32 (2006.01)
`AOIN 35/06 (2006.01)
`C07C 49/517 (2006.01)
`
`(81)
`
`QD
`
`International Application Number:
`
`PCT/EP2015/063744
`
`(22)
`
`International Filing Date:
`
`Filing Language:
`
`Publication Language:
`
`18 June 2015 (18.06.2015)
`
`English
`
`English
`
`(25)
`
`(26)
`
`(30)
`
`(71)
`
`(72)
`
`Priority Data:
`1411418.5
`
`26 June 2014 (26.06.2014)
`
`GB
`
`SYNGENTA PARTICIPATIONS AG
`Applicant:
`[CH/CH]; Schwarzwaldallee 215, 4058 Basel (CH).
`
`Inventors: SCUTT, James Nicholas; Syngenta Limited,
`Jealott's IIill
`International Research Centre, Bracknell,
`Berkshire RG42 6EY (GB). WILLETTS, Nigel James;
`Syngenta Limited, Jealott's Hill
`International Research
`Centre, Bracknell, Berkshire RG42 6EY (GB).
`
`(84)
`
`Designated States (unless otherwise indicated, for every
`kind of regional protection available): ARIPO (BW, GH,
`GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ,
`TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU,
`TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE,
`DK,EE,ES, FI, FR, GB, GR, HR, HU,IE, IS, IT, LT, LU,
`LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK,
`SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ,
`GW, KM, ML, MR, NE, SN, TD, TG).
`Declarations under Rule 4.17:
`
`(74)
`
`Agent: SYNGENTA INTERNATIONAL AG;Intellectu-
`al Property, WRO 1008-21-26, Schwarzwaldallee 215,
`4058 Basel (CH).
`
`of inventorship (Rule 4.17(iv))
`Published:
`
`with international search report (Art. 21(3))
`
`(54) Title: HERBICIDAL PROPYNYL-PHENYL COMPOUNDS
`
`
`
`(I)
`
`(57) Abstract: The present invention relates to a compound of formula (1) wherein: R! is C:-Csalkoxy, Ci-Coalkoxy-Ci-Csalkoxy,
`C1-Cofluoroalkoxy, ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl; R? is hydrogen, ethyl, “-propyl, cyclopropyl, vinyl, ethynyl, C:-
`Caalkoxy, Ci-Cafluoroalkyl, C\-C2fluoroalkoxy, C)-Coalkoxy-C1-Czalkoxy-, or C:fluoroalkoxy-Ci-Csalkoxy-; provided that when R’
`is ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl, then R? is hydrogen, ethyl, n-propyl, cyclopropyl, vinyl or ethynyl; and Y is O, S,
`SCO), S(O)2, N(C1-Caalkyl), N(Ci-Coalkoxy), C(O), CR§R® or -CR™R"'CRPR'3-; and and G, R?, R4, R° and R¢ are as defined herein;
`wherein the compound offormula (Dis optionally present as an agrochemically acceptable salt thereof. These compoundsare suit -
`able for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledon-
`ous weeds, in crops of useful plants, comprising applying a compoundof formula (1), or a herbicidal composition comprising such a
`compound, to the plants or to the locus thereof.
`
`wo2015/197468A1IIITINMIIMTAIMAATAA
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`HERBICIDAL PROPYNYL-PHENYL COMPOUNDS
`
`The present invention relates to herbicidally active cyclic diones,
`
`in particular pyrandione,
`
`thiopyrandione, cyclohexanedione, alkanediyl-bridged cyclohexanedione, cyclohexanetrione
`
`or cycloheptanedione compounds, or derivatives thereof
`
`(e.g. enol ketone tautomer
`
`derivatives thereof), to processesfor their preparation, to herbicidal compositions comprising
`
`those compounds, and to their use in controlling weeds such as grassy monocotyledonous
`
`weeds, especially in crops of useful plants, or in inhibiting undesired plant growth.
`
`In
`
`particular,
`
`the present invention relates to herbicidally active cyclic dione compounds, or
`
`10
`
`derivatives thereof (e.g. enol ketone tautomerderivatives thereof), which are substituted by a
`
`phenyl which has an alkynyl-containing substituent.
`
`WO 01/17972 discloses phenyl-substituted (such as 4-methyl-2,6-diethyl-phenyl- substituted)
`
`heterocycles suitable for use as herbicides.
`
`15
`
`WO 03/013249 disclose selective herbicidal compositions comprising (a) a (substituted-
`
`phenyl)-substituted cyclic ketoenol and (b) a compound which improves crop plant
`
`compatibility, in particular cloquintocet-mexyl or mefenpyr-diethyl.
`
`20
`
`WO 2007/068427 disclose a composition comprising (a) a (substituted-phenyl)-substituted
`
`cyclic ketoenol as a herbicide, and (b) an ammonium or phosphonium salt to boost activity.
`
`WO 2008/071405 and WO 2009/074314 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
`
`25
`
`cyclic dione or trione by an aryl-substituted-phenyl or by a heteroary!-substituted-phenyl.
`
`WO 2010/081755 and WO 2010/089211 each disclose herbicidally active pyran-3,5-diones,
`
`thiopyran-3,5-diones, cyclohexanediones, cycloheptanediones and cycilohexanetriones, each
`
`substituted by an aryloxy-substituted-phenyl or by a heteroaryloxy-substituted-phenyl.
`
`30
`
`WO 2008/110308 discloses 2-(substituted-phenyl)-cyclohexane-1,3-dione compounds and
`derivatives, containing a R®-X-(CR°R’),- substituent (wherein X is O, S, S(O) or S(O)) or a
`heteroatom-containing-spirocyle at the 5-position of the cyclohexane-1,3-dione, and having
`
`herbicidal properties. WO 2008/110307 A1 discloses 2-(substituted-phenyl)-5-heterocyclyl-
`
`35
`
`cyclohexane-1,3-dione compounds and derivatives, and their use as herbicides. WO
`
`2010/046194
`
`discloses
`
`2-(substituted-phenyl)-cyclohexane-1,3-dione
`
`compounds
`
`and
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`derivatives, containing a Q-CR®R’- 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 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.
`
`WO 2013/079672 discloses that certain substituted spiroheterocyclic pyrrolidine dione
`
`10
`
`compounds, having an alkynyl-phenyl- headgroup, have herbicidal properties.
`
`WO 2013/079708 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
`
`15
`
`(specifically) either prop-1-ynyl or chloroethynyl and at the 2-position by (specifically) 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.
`
`20
`
`WO 2014/096289 discloses cyclic dione compounds, more particularly pyran-3,5-dione,
`
`thiopyran-3,5-dione,
`
`cyclohexane-1,3-dione,
`
`alkanediyl-bridged
`
`cyclohexane-1,3-dione,
`
`cyclohexane-1,3,5-trione or cycloheptane-1,3-dione compounds, which are substituted, at
`
`the ring-carbon atom of the cyclic dione which is between the two oxo-substituted ring-
`
`carbons of the cyclic dione, by a phenyl which itself is substituted at the 4-position by
`
`25
`
`(specifically) either prop-1-ynyl or chloroethynyl and at the 2-position by (specifically) methyl
`
`or chlorine, or derivatives of the enol ketone tautomer of such cyclic diones, which have
`
`herbicidal activity and/or plant-growth-inhibiting properties,
`
`in particular in the control of
`
`grassy monocotyledonous weeds.
`
`30
`
`Novel cyclic dione compounds, more particularly pyran-3,5-dione,
`
`thiopyran-3,5-dione,
`
`cyclohexane-1,3-dione, alkanediyl-bridged cyclohexane-1,3-dione, cyclohexane-1,3,5-trione
`
`or cycloheptane-1,3-dione compounds, which are substituted, at the ring-carbon atom of the
`
`cyclic dione which is between the two oxo-substituted ring-carbons of the cyclic dione, by a
`
`phenyl whichitself is substituted at the 4-position by (specifically) prop-1-ynyl and at the 2-
`
`35
`
`position by (specifically) certain C2 or greater alkyl groups or certain alkoxy or fluoroalkoxy
`
`groups, or derivatives of the enol ketone tautomer of such cyclic diones, which have
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`herbicidal activity and/or plant-growth-inhibiting properties,
`
`in particular in the control of
`
`grassy monocotyledonous weeds.
`
`Therefore, in a first aspect of the present invention, there is provided a compound of formula
`
`(I):
`
`
`
`wherein:
`
`10
`
`R'
`
`is C,-Cgalkoxy, Cy-Czalkoxy-C)-Caalkoxy, Cy-Cfluoroalkoxy, ethyl, n-propyl, n-butyl,
`
`cyclopropyl or ethyny];
`
`R? is hydrogen, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, C,-Czalkoxy, C,-C3fluoroalkyl,
`
`15
`
`C,-Cefluoroalkoxy, C,-Czalkoxy-C,-Caalkoxy-, or C,fluoroalkoxy-C1-Csalkoxy-;
`
`provided that when R’is ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl, then R?is hydrogen,
`
`ethyl, n-propyl, cyclopropyl, vinyl or ethynyl; and
`
`20
`
`R*, R*, R® and R®°, independently of each other, are hydrogen, C,-Csalkyl (in particular C,-
`
`Caalkyl, e.g. Ci-Czalkyl), C2-Cyalkenyl
`
`(in particular C2-Csalkenyl-CH2-, e.g. ethenyl-CH>-),
`
`Cp-Cyalkynyl
`
`(in
`
`particular C2-Csalkynyl-CH2-,
`
`e.g.
`
`ethynyl-CHe2-),
`
`Cy1-Cefluoroalkyl,
`
`C,-CsalkoxyC,-Cazalkyl,
`
`C,-CaalkylthioC,-Csalkyl,
`
`C,-CaalkylsulfinylC,-Cgalkyl,
`
`C,-CgalkylsulfonylC,;-Csalkyl; C3-C4cycloalkyl
`
`(in particular cyclopropyl); or an unsubstituted
`
`25
`
`4, 5 or 6 (e.g. 4 or 5) membered monocyclic heterocyclyl having one ring heteroatom
`
`independently selected from oxygen, sulfur and nitrogen, and attached at a ring carbon atom
`
`within the heterocyclyl
`
`(in particular tetrahydrofuranyl such as_
`
`tetrahydrofuran-3-yl, or
`
`tetrahydropyranyl such as tetrahydropyran-4-yl);
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`provided that no more than one (in particular none) of R®, R*, R® and R°is alkenyl, alkynyl,
`
`alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
`
`or R® and R‘ taken together are -(CH2)m- or -(CH2)no-X'-(CH2)n3- and R°® and R® are as
`defined
`herein
`(e.g.
`hereinabove),
`or
`R®
`and
`R®
`taken
`together
`are -(CHa)n1- or -(CH2)no-X'-(CH2)na- and R® and R‘ are as defined herein (e.g. hereinabove);
`wherein X'
`is O, S, S(O), S(O), NH, N(Cy-Czalkyl), N(Cy-Czalkoxy), C(H)(Ci-Czalkyl),
`
`C(C.1-Caalkyl)2 or C(H)(C1-C2alkoxy);
`
`n1 is 2, 3, 4 or 5 (in particular 4 or 5); and
`
`10
`
`n2 and n3 are independently 1, 2 or 3 provided that n2 + n3 is 2, 3 or 4 (in particular 3 or 4);
`
`or R* and R® taken together are -(CH2)n4- or -(CH2)ps-C(R”)(R”)-(CH2)ne- or -C(R”)=C(R”™)-;
`wherein R” is C,-Czalkyl or C)-Czalkoxy; and R”is hydrogen or C,-Czalkyl provided that R”
`is hydrogen when R”? is C,-Czalkoxy;
`
`15
`
`n4 is 1, 2 or 3; and
`
`n5 and n6 are independently O, 1 or 2 provided that n5 + n6 is O, 1 or 2;
`and R” and R™independently are hydrogen or Cy-Czalkyl; and
`
`Y is O, S, S(O), S(O)z, N(C1-Czalkyl), N(C1-Czalkoxy), C(O), CR®R® or -CR®R™CR”?R™-; and
`
`20
`
`R® and R® are, independently of each other:
`
`hydrogen, Cy,-Cealkyl
`
`(in particular Cy,-Cyalkyl, e.g. C1-Czalkyl), C2-Cyalkenyl
`
`(in
`
`particular
`
`C,-Czalkenyl-CH2-,
`
`e.g.
`
`ethenyl-CH--),
`
`C2-C,alkynyl
`
`(in
`
`particular
`
`C2-Csalkynyl-CH>-,
`
`e.g.
`
`ethynyl-CH>-),
`
`C,-C2fluoroalkyl,
`
`C,-CgalkoxyC,-Caalkyl,
`
`25
`
`C,-CgalkylthioC,-Caalkyl, C;-CaalkylsulfinylC,-Czalkyl, or C;-CgalkylsulfonylC,-Caalkyl;
`
`C3-Cecycloalkyl or Cs3-Cecycloalkyl substituted by one or
`
`two substituents which
`
`independently are C,-Cgalkyl (in particular methyl or ethyl) or C,-C2fluoroalkyl; and in which
`
`one ring CH2 moiety of a Cy-Cecycloalkyl is optionally (e.g. preferably) replaced by an oxygen
`
`or sulfur atom or by a S(O), S(O)2, NH, N(C.-Csalkyl), N(C.-C2fluoroalkyl), N[C(O)C,-Czalkyl],
`
`30
`
`N[C(O)C,-C2fluoroalkyl] or N(C,-Czalkoxy) moiety;
`
`Cz-Cecycloalkyl
`
`substituted by one substituent being Cy ,-Csalkoxy (in particular
`
`C,-Czalkoxy) and optionally further substituted by one substituent being C,-Czalkyl
`
`(in
`
`particular methyl);
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`Cs5-Cecycloalkenyl or Cs5-Cecycloalkenyl substituted by one or
`
`two C,-Cgalkyl
`
`(in
`
`particular methyl) substituents;
`
`C3-CecycloalkylC,-Czalkyl- (in particular C3-Cecycloalkylmethyl-) or Cs-CecycloalkylC,-
`
`Czalkyl- (in particular C3-Cecycloalkylmethyl-) substituted by one or two ring substituents
`
`which independently are C,-Caalkyl or C,-Czfluoroalkyl; and in which one ring CH» moiety of a
`
`C4-CecycloalkylC,-Caalkyl- (in particular C4-Cecycloalkylmethyl-) is optionally (e.g. preferably)
`
`replaced by an oxygen or sulfur atom or by a S(O), S(O}, NH, N(C.-Czalkyl), N(C1-
`
`Cflucroalkyl), N[C(O)C,-Czalkyl], N[C(Q)C,-C2fluoroalkyl] or N(C1-Czalkoxy) moiety;
`
`C2-CecycloalkylC1-Czalkyl- (in particular C3-Cecycloalkylmethyl-) substituted by one ring
`
`10
`
`substituent being C,-Czalkoxy (in particular C,-Czalkoxy) and optionally further substituted by
`
`one ring substituent being C1-Czalkyl (in particular methyl); or
`
`Het or Het-CH2-, wherein Het
`
`is a heteroaryl, attached at a ring-carbon, which is
`
`optionally substituted by 1, 2 or 3 (in particular 1 or 2, e.g. 1) ring-carbon substituents
`
`independently
`
`being Cy,-Csalkyl
`
`(e.g. Cy-Cealkyl),
`
`Cy 1-Cefluoroalkyl, C1-Cs3alkyl-C(O)-,
`
`15
`
`C,-Cfluoroalkyl-C(O)-, hydroxy (including any oxo tautomer), C2-Cgalkenyl (e.g. ethenyl or
`
`prop-1-enyl), C2-Csalkynyl (e.g. ethynyl or prop-1-ynyl), C1-Csalkoxy (e.g. Ci-Czalkoxy), C.-
`
`C-fluoroalkoxy, halogen (e.g. fluorine or chlorine), cyano or nitro, provided that any non-
`
`fluorine halogen, alkoxy or fluoroalkoxy is not substituted at any ring-carbon bondeddirectly
`
`to a ring-nitrogen of the heteroaryl; and/or,
`
`in the case of a 5-membered heteroaryl ring
`
`20
`
`containing a ring-nitrogen atom not partaking in a C=N ring double bond, the heteroaryl is
`
`optionally substituted on the ring-nitrogen atom not partaking in a C=N ring double bond by
`
`one
`
`C,-Caalkyl,
`
`C,-C2fluoroalkyl,
`
`C,-Czalkyl-C(O)-,
`
`C,-C2fluoroalkyl-C(O)-
`
`or
`
`C,-Czalkyl-S(O)>- substituent;
`
`25
`
`provided that no more than one of R® and R’® is an optionally substituted cycloalkyl; an
`optionally substituted cycloalkyl
`in which one ring CH2 moiety has been replaced by an
`
`oxygen or sulfur atom or by a S(O), S(O), NH, N(Cy-Caalkyl), N(C1-Cofluoroalkyl),
`
`
`
`N[C(O)C,-Caalkyl], N[C(O)C.-C2fluoroalkyl] an_optionallyor N(C1-Czalkoxy) moiety;
`
`
`
`substituted cycloalkenyl; an optionally substituted cycloalkyl-alkyl-; an optionally substituted
`
`30
`
`cycloalkyl-alkyl- in which one ring CH2z moiety has been replaced by an oxygen or sulfur atom
`
`or
`
`by
`
`a
`
`S(O),
`
`S(O)z, NH, N(Cy-Cegalkyl), N(C.-Cofluoroalkyl), N[C(O)C,-Caalkyl],
`
`N[C(O)C,-C2fluoroalkyl] or N(C1-Czalkoxy) moiety; or Het or Het-CH-2-;
`
`or R® is hydrogen or C;-Czalkyl (in particular H or Me), and R® is C1-Czalkoxy(in particular
`methoxy);
`
`35
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`or R® and R® taken together are -(CH2)n7- or -(CH2)ns-X*-(CH2)no-3
`wherein X? is O, S, S(O), S(O)z, NH, N(Cy-Caalkyl), N(C-C2fluoroalkyl), N[C(O)C)-Czalkyl],
`N[C(O)C,-Cofluoroalkyl],
`N(C.1-Czalkoxy),
`C(H)(C1-Caalkyl),
`C(C1-Caalkyl),
`or
`
`C(H)(C1-Cgalkoxy);
`
`n7 is 2, 3, 4, 5 or 6 (in particular 4 or 5); and
`
`n8 and n9 are independently 0, 1, 2 or 3 provided that n8 + n9 is 2, 3, 4 or 5 (in particular 3
`
`or 4); and
`
`R', R™, R’ and R™ are independently of each other hydrogen or Cy-Cyalkyl (in particular
`C,-Czalkyl) provided that no more than one of R", R"', R and R" is C3-Cyalkyl; and
`
`10
`
`and wherein:
`
`G is hydrogen; an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or
`
`ammonium group; or
`
`15
`
`G is
`
`-C(X?)-R?,
`
`-C(X°)-X°-R®,
`
`-C(X°)-N(R°)-R°,
`
`-SO2-R®,
`
`-P(X°)(R‘)-R9,
`
`-CH-X'-R"; or
`
`phenyl-CHz2- or phenyl-CH(C,-Czalkyl)- (in each of which the phenyl is optionally substituted
`
`by 1, 2 or 3 of, independently, C,-Czalkyl, C,fluoroalkyl, C;-Czalkoxy, C,fluoroalkoxy, fluorine,
`
`chlorine, bromine, cyano or nitro), or heteroaryl-CH»2- or heteroaryl-CH(C,-Czalkyl)- (in each
`
`20
`
`of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-Czalkyl,
`
`C,fluoroalkyl, C,-Czalkoxy, C,fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or
`
`phenyl-C(O)-CH,- (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently,
`
`C,-Czalkyl, Cifluoroalkyl, C1-Czalkoxy, Cfluoroalkoxy, fluorine, chlorine, bromine, cyano or
`
`nitro);
`
`or
`
`Cy-Cgalkoxy-C(O)-CH2-,
`
`Cy ,-Cesalkoxy-C(O)-CH=CH-,
`
`C2-C7alken-1-yl-CH2-,
`
`25
`C2-Czalken-1-yl-CH(C,-Czalkyl)-,=C2-C,fluoroalken-1-yl-CH2-,=C2-Czalkyn-1-yl-CH2-,—or
`
`C2-Czalkyn-1 -yl-CH(C,-Caalkyl)-;
`
`wherein X*, X°, X°, X°, X° and X' are independently of each other oxygen or sulfur (
`
`in
`
`particular oxygen); and wherein
`
`30
`
`R* is H, Cy-Ca,alkyl, C2-C2,alkenyl, C2-Cigalkynyl, C1-Ciofluoroalkyl, C;-C,>cyanoalkyl, C4-
`
`Cyonitroalkyl, C-Cipaminoalkyl, C-Csalkylamino(C,-Cs)alkyl, C2-Cedialkylamino(C,-Cs)alkyl,
`
`C3-C7cycloalkyl(C1-Cs)alkyl,
`
`C1-Csalkoxy(C1-Cs)alkyl,
`
`Cs-Csalkenyloxy(C.1-Cs)alkyl,
`
`Csalkynyloxy
`
`(C4-Cs)alkyl, Cy-Csalkylthio(C,-Csjalkyl, C)-Csalkylsulfinyl(C;-Cs)alkyl,
`
`Ca-
`
`Cy4-
`
`35
`
`Csalkylsulfonyl(C1-Cs)alkyl,
`
`C2-Cealkylideneaminoxy(C.1-Cs)alkyl,
`
`C,-Csalkylcarbonyl(C,-
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`-7-
`
`Cs)alkyl,
`
`C,-Csalkoxycarbonyl(C,-Cs)alkyl,
`
`aminocarbonyl(C,-Cs)alkyl,
`
`Csalkylaminocarbonyl(C,-Cs)alkyl,
`
`C2-Cedialkylaminocarbonyl(C,-Cs)alkyl,
`
`Ci-
`
`Ci-
`
`Csalkylcarbonylamino(C,-Cs)alkyl,=N-(C,-Cs)alkylcarbonyl-N-(C1-Cs)alkylamino(C.-Cs)alkyl,
`
`C3-Cetrialkylsilyl(C;-Cs)alkyl, phenyl(C1-Cs)alkyl (wherein the phenyl is optionally substituted
`
`by 1, 2 or 3 of, independently, C,-Czalkyl, C,-Cefluoroalkyl, C;-Czsalkoxy, C,-Cefluoroalkoxy,
`
`C,-Caalkylthio, C1-Cgalkylsulfinyl, C1-Csalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C,.-
`
`Cs)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C,-
`
`Caalkyl, C4-Cefluoroalkyl, C;-Csalkoxy, C1-Csfluoroalkoxy, C,-Csalkylthio, C,-Czalkylsulfinyl,
`
`C,-Czalkylsulfonyl, halogen, cyano, or nitro), Co-Csfluoroalkenyl, Cs-Cgcycloalkyl; phenyl or
`
`10
`
`phenyl substituted by 1, 2 or 3 of, independently, C:-Csalkyl, C.-C3fluoroalkyl, C;-Czalkoxy,
`
`C,-Czfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
`
`of,
`
`independently, C,-Cz alkyl, C,-Cezfluoroalkyl, C,-Csalkoxy, C,-Csfluoroalkoxy, halogen,
`
`cyano or nitro;
`
`15
`
`R°
`
`is Cy-Cygalkyl, C3-Cigalkenyl, C3-Cigalkynyl, C2-Cyofluoroalkyl, C-Ciocyanoalkyl, C,-
`
`Cyonitroalkyl, C2-Cisaminoalkyl, C.-Csalkylamino(C1-Cs)alkyl, C2-Csdialkylamino(C,-Cs)alkyl,
`
`C3-C,cycloalkyl(C1-Cs)alkyl,
`
`Cy ,-Csalkoxy(C-Cs)alkyl,
`
`C3-Csalkenyloxy(C,-Cs)alkyl,
`
`Cz-
`
`
`
`Csalkynyloxy(C,-Cs)alkyl, C1-Csalkylsulfinyl(C4-Cs)alkyl,=Cy-Cy-Csalkylthio(C,-Cs)alkyl,
`
`
`
`Csalkylsulfonyl(C1-Cs)alkyl,
`
`C2-Cgalkylideneaminoxy(C.-Cs)alkyl,
`
`C,-Csalkylcarbonyl(C,-
`
`20
`
`Cs)alkyl,
`
`C,-Csalkoxycarbonyl(C,-Cs)alkyl,
`
`aminocarbonyl(C1-Cs)alkyl,
`
`Csalkylaminocarbonyl(C1-Cs)alkyl,
`
`C2-Cedialkylaminocarbonyl(C,-Cs)alkyl,
`
`Ci-
`
`Ci-
`
`Csalkylcarbonylamino(C,-Cs)alkyl,|N-(C,-Cs)alkylcarbonyl-N-(C1-Cs)alkylamino(C.-Cs)alkyl,
`
`C3-Cetrialkylsilyl(C;-Cs)alkyl, phenyl(C1-Cs)alkyl (wherein the phenyl is optionally substituted
`
`by 1, 2 or 3 of, independently, C,-Csalkyl, C,-Csfluoroalkyl, C;-C3alkoxy, C,-Csfluoroalkoxy,
`
`25
`
`C,-Cgalkylthio, C,-Czalkylsulfinyl, C;-Cgalkylsulfonyl, halogen, cyano, or nitro), heteroarylC,-
`
`Csalkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C.-
`
`Cgalkyl, C1-C3fluoroalkyl, C,-Csalkoxy, C,-Csfluoroalkoxy, C,-Cgalkyl-thio, C)-C3alkylsulfinyl,
`
`C,-Cgalkylsulfonyl, halogen, cyano, or nitro), Cz-Csfluoroalkenyl, Cs-Cgcycloalkyl; phenyl or
`
`phenyl substituted by 1, 2 or 3 of, independently, Ci-Csalkyl, C.-C3fluoroalkyl, C;-Czalkoxy,
`
`30
`
`C,-Czfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3
`
`of,
`
`independently, C,-Cz alkyl, C,-Cezfluoroalkyl, C,-Csalkoxy, C,-Csfluoroalkoxy, halogen,
`
`cyano or nitro; and
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`-8-
`
`R° and R° are each independently of each other hydrogen, C1-Cyoalkyl, C3-Cioalkenyl, C3-
`
`Cyoalkynyl, C2-Ciofluoroalkyl, C1-Cyocyanoalkyl, C,4-Cyonitroalkyl, Cy-Ci9aminoalkyl,
`
`Csalkylamino(C,-Cs)alkyl, C2-Csdialkylamino(C,-Cs)alkyl, Cs-C7cycloalkyl(C1-Cs)alkyl,
`
`Csalkoxy(C,-Cs)alkyl,
`
`C3-Csalkenyloxy(C,-Cs)alkyl,
`
`C3-Csalkynyloxy(C4-Cs)alkyl,
`
`Csalkylthio(C,-Cs)alkyl, C.-Csalkylsulfinyl(C1-Cs)alkyl,
`
`C1-Csalkylsulfonyl(C1-Cs5)alkyl,
`
`Cy,-
`
`C,4-
`
`Ci-
`
`Co-
`
`Cealkylideneaminoxy(Ci-Cs)alkyl, C1-Csalkylcarbonyl(C.-Cs)alkyl, C1-Csalkoxycarbonyl(C.-
`
`Cs)alkyl,
`
`aminocarbonyl(C,-Cs)alkyl,
`
`C,-Csalkylaminocarbonyl(C,-Cs)alkyl,
`
`C2-
`
`Cedialkylaminocarbonyl(C,-Cs)alkyl,
`
`C,-Csalkylcarbonylamino(C,-Cs)alkyl,
`
`N-(Cy-
`
`Cs)alkylcarbonyl-N-(C2-Cs)alkylaminoalkyl, C3-Cetrialkylsilyl(C1-Cs)alkyl,
`
`phenyl(C;-Cs)alkyl
`
`10
`
`(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, Ci-Caalkyl, C.-
`
`C3flucroalkyl,
`
`Cy-Csalkoxy,
`
`C1-Csfluoroalkoxy,
`
`Cy ,-Csalkylthio,
`
`C,-Csalkylsulfinyl,
`
`Cy,-
`
`Caalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C;-C;)alkyl (wherein the heteroaryl
`
`is
`
`optionally substituted by 1, 2 or 3 of,
`
`independently, C.,-Csalkyl, C,-Csfluoroalkyl, C,-
`
`Czalkoxy, C,-Csfluoroalkoxy, C,-Cgalkylthio, C,-Cz3alkylsulfinyl, C,-Cs3alkylsulfonyl, halogen,
`
`15
`
`cyano, or nitro), C2-C;fluoroalkenyl, Cs-Cgcycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
`
`of,
`
`independently, C,-Csalkyl, C.-Csfluoroalkyl, C.-Csalkoxy, C,-Csfluoroalkoxy, halogen,
`
`cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C)-Csalkyl,
`
`C,-Cefluoroalkyl, C;-Czsalkoxy, C1-C2fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
`
`heteroarylamino substituted by 1, 2 or 3 of, independently, C,-Csalkyl, C1-Csfluoroalkyl, C,-
`
`20
`
`Czalkoxy, C,-Czfluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
`
`substituted by 1, 2 or 3 of,
`
`independently, C,-Csalkyl, C1-Csfluoroalkyl, C,-Csalkoxy, Cy-
`
`Czfluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
`
`of,
`
`independently, C,-Csgalkyl, C,-C3fluoroalkyl, C4-Cs3alkoxy, C,-Csfluoroalkoxy, halogen,
`
`cyano or bynitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently,
`
`25
`
`C,-Caalkyl, C1-Czfluoroalkyl, C,-Csalkoxy, C;-C2fluoroalkoxy, halogen, cyano or nitro; or Cs-
`
`C,cycloalkylamino, di(C3-C;cycloalkylamino or C3-C;cycloalkoxy;
`or R° and R’‘, together with the nitrogen to which they are bonded, to form an unsubstituted 4,
`
`5, 6 or 7 (e.g. 5 or 6) memberedring, optionally containing one heteroatom selected from O
`
`or S; and
`
`30
`
`R®°
`
`is Cy-Cyoalkyl, C2-Cioalkenyl, Co-Cioalkynyl, C4-C,ofluoroalkyl, C,-Ciocyanoalkyl, Cy.-
`
`Cionitroalkyl, C-Cisaminoalkyl, C1-Csalkylamino(C1-Cs)alkyl, Co2-Cedialkylamino(C1-Cs)alkyl,
`
`C3-C,cycloalkyl(C4-Cs)alkyl,
`
`Cy ,-Csalkoxy(C-Cs)alkyl,
`
`C3-Csalkenyloxy(C,-Cs)alkyl,
`
`C3-
`
`
`
`Csalkynyloxy(C,-Cs)alkyl, C1-Csalkylsulfinyl(C-Cs)alkyl,=Cy-Cy 4-Csalkylthio(C,-Cs)alkyl,
`
`
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`Csalkylsulfonyl(C,-Cs)alkyl,
`
`C.-Cgalkylideneaminoxy(C,-Cs)alkyl,
`
`C,-Csalkylcarbonyl(C,-
`
`Cs)alkyl,
`
`C,-Csalkoxycarbonyl(C1-Cs)alkyl,
`
`aminocarbonyl(C,-Cs)alkyl,
`
`Csalkylaminocarbonyl(C.-Cs)alkyl,
`
`C2-Cedialkylaminocarbonyl(C,-Cs)alkyl,
`
`Ci-
`
`C.-
`
`Csalkylcarbonylamino(C,-Cs)alkyl,§N-(C,-Cs)alkylcarbonyl-N-(C,-Cs)alkylamino(C,-Cs)alkyl,
`
`C3-Cetrialkylsilyl(C1-Cs)alkyl, phenyl(C1-Cs)alkyl (wherein the phenyl is optionally substituted
`
`by 1, 2 or 3 of, independently, C,-Csalkyl, C1-Csfluoroalkyl, C1-Csalkoxy, C1-Csfluoroalkoxy,
`
`C,-Caalkylthio, C;-Cgalkylsulfinyl, C;-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C,-
`
`Cs)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C,-
`
`Caalkyl, C.1-Cesfluoroalkyl, C;-Csalkoxy, C1-Csfluoroalkoxy, C,-Csalkylthio, C,-Czalkylsulfinyl,
`
`10
`
`C,-Czgalkylsulfonyl, halogen, cyano, or nitro), C2-Csfluoroalkenyl, C3-Cgcycloalkyl; phenyl or
`
`phenyl substituted by 1, 2 or 3 of, independently, C,-Csalkyl, C,-Csfluoroalkyl, C,-Csalkoxy,
`
`C,-Czfluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of,
`
`independently, C,-Czsalkyl, C,-Csfluoroalkyl, C,-Csalkoxy, C,-Csfluoroalkoxy, halogen, cyano
`
`or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C,-Cz
`
`15
`alkyl, or_nitro;Cy,-Czfluoroalkyl, C,-Csalkoxy, Cy ,-C2fluoroalkoxy, halogen, cyano
`
`
`
`
`
`
`
`
`
`
`
`diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C;-Csalkyl,
`
`C,-Czfluoroalkyl, C,-Csalkoxy, C,-Czfluoroalkoxy, halogen, cyano or nitro; phenylamino or
`
`phenylamino substituted by 1, 2 or 3 of,
`
`independently, C1-Czalkyl, C,-Cefluoroalkyl, C,-
`
`Czalkoxy, C.-Csfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino
`
`20
`
`substituted by 1, 2 or 3 of,
`
`independently, C,-Csalkyl, C,-Cs3fluoroalkyl, C;-C3alkoxy, Cy-
`
`Czflucroalkoxy, halogen, cyano or nitro; or Cs-C7cycloalkylamino, di(C3-C7cycloalkyl)amino,
`
`C3-C7cycloalkoxy, C1-Cisalkoxy, C1-Ciofluoroalkoxy, C1-Csalkylamino or di(C1-Caalkyl)amino;
`
`R' and R® are each independently of each other Cy-Cyoalkyl, C2-Cyoalkenyl, C2-Cyoalkynyl, C,-
`
`25
`
`Cyioalkoxy, Cy-Criofluoroalkyl, Cy-C1scyanoalkyl, Cy-Cyonitroalkyl, C1-C1paminoalkyl,
`
`Csalkylamino(C,-Cs)alkyl, C2-Cedialkylamino(C,-Cs)alkyl, Cs-C7cycloalkyl(C1-Cs)alkyl,
`
`Csalkoxy(C,-Cs)alkyl,
`
`C3-Csalkenyloxy(C,-Cs)alkyl,
`
`C3-Csalkynyloxy(C1-Cs)alkyl,
`
`Csalkylthio(C,-Cs)alkyl, C,-Csalkylsulfinyl(C4-Cs)alkyl, C1-Csalkylsulfonyl(C4-Cs)alkyl,
`
`Cy.-
`
`C,4-
`
`Cr-
`
`Co-
`
`Cgalkylideneaminoxy(C.-Cs)alkyl, C.1-Csalkylcarbonyl(C,-Cs)alkyl, Ci-Csalkoxycarbonyl(C,.-
`
`30
`
`Cs)alkyl,
`
`aminocarbonyl(C,-Cs)alkyl,
`
`C,-Csalkylaminocarbonyl(C,-Cs)alkyl,
`
`C2-
`
`Cedialkylaminocarbonyl(C,-Cs)alkyl,
`
`C,-Csalkylcarbonylamino(C,-Cs)alkyl,
`
`N-(Cy-
`
`Cs)alkylcarbonyl-N-(C2-Cs)alkylaminoalkyl, C3-Cetrialkylsilyl(C;-Cs)alkyl,
`
`phenyl(C;-Cs)alkyl
`
`(wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C,-Csalkyl, C,-
`
`Czflucroalkyl,
`
`Cy-Csalkoxy,
`
`Cy1-Csfluoroalkoxy,
`
`Cy,-Csalkylthio,
`
`C,-Czsalkylsulfinyl,
`
`Cy,-
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`-10-
`
`Czgalkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C,-Cs)alkyl (wherein the heteroaryl
`
`is
`
`optionally substituted by 1, 2 or 3 of,
`
`independently, C,-Caalkyl, C,-Cefluoroalkyl, C,-
`
`Czalkoxy, C.-Csfluoroalkoxy, C.-Csalkylthio, C.-Csalkylsulfinyl, C,-Csalkylsulfonyl, halogen,
`
`cyano, or nitro), C2-Csfluoroalkenyl, C3-Cgcycloalkyl; phenyl or phenyl substituted by 1, 2 or 3
`
`of,
`
`independently, C,-Czgalkyl, C,-C2fluoroalkyl, C,-Czalkoxy, C,-C2fluoroalkoxy, halogen,
`
`cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-Cz3 alkyl,
`
`C,-Czfluoroalkyl, C,-C3alkoxy, C;-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or
`
`heteroarylamino substituted by 1, 2 or 3 of, independently, C1-Cz alkyl, C1-Cafluoroalkyl, C4-
`
`Czalkoxy, C1-C2fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino
`
`10
`
`substituted by 1, 2 or 3 of,
`
`independently, Ci-Cz alkyl, C1-Csfluoroalkyl, C-Csalkoxy, C.-
`
`C3flucroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3
`
`of,
`
`independently, C,-Cgalkyl, C,-C2fluoroalkyl, C1-Czalkoxy, C,-C2fluoroalkoxy, halogen,
`
`cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C,-
`
`Cgalkyl, C1-Csfluoroalkyl, C;-Csalkoxy, C,-Cs3fluoroalkoxy, halogen, cyano or nitro; or Cs3-
`
`15
`
`Cr7cycloalkylamino,
`
`di(C3-Czcycloalkyl)amino, Czg-C7cycloalkoxy,
`
`Cy ,-Ciofluoroalkoxy,
`
`Cy.-
`
`Csalkylamino or di(C.-C,alkylamino; or benzyloxy or phenoxy, wherein the benzyl and
`
`phenyl groups arein turn optionally substituted by 1, 2 or 3 of, independently, C;-Csalkyl, C,-
`
`C2flucroalkyl, C,-Czgalkoxy, C;-C3fluoroalkoxy, halogen, cyano or nitro; and
`
`20
`
`R"
`
`is Cy-Cyoalkyl, C3-Cyoalkenyl, C3-Cialkynyl, C4-Ciofluoroalkyl, C-Cy9cyanoalkyl, C,-
`
`Cyonitroalkyl, C2-Cipaminoalkyl, C.-Csalkylamino(C,-Cs)alkyl, C2-Cedialkylamino(C,-Cs)alkyl,
`
`C3-C7cycloalkyl(C1-Cs)alkyl,
`
`C1-Csalkoxy(C1-Cs)alkyl,
`
`Cs-Csalkenyloxy(C.1-Cs)alkyl,
`
`Csalkynyloxy(C,-Cs)alkyl,
`
`C,-Csalkylthio(C,-Cs)alkyl,
`
`C,-Csalkylsulfinyl(C;-Cs)alkyl,
`
`Ca-
`
`Cy-
`
`Csalkylsulfonyl(C1-Cs)alkyl,
`
`C2-Cgalkylideneaminoxy(C,1-Cs)alkyl,
`
`C,-Csalkylcarbonyl(C,-
`
`25
`
`Cs)alkyl,
`
`C,-Csalkoxycarbonyl(C.1-Cs)alkyl,
`
`aminocarbonyl(C,-Cs)alkyl,
`
`Csalkylaminocarbonyl(C.-Cs)alkyl,
`
`C2-Cedialkylaminocarbonyl(C,-Cs)alkyl,
`
`Ci-
`
`C.-
`
`Csalkylcarbonylamino(C,-Cs)alkyl,
`
` N-(C1-Cs)alkylcarbonyl-N-(C1-Cs)alkylamino(C1-Cs)alkyl,
`
`C3-Cetrialkylsilyl(C1-Cs)alkyl, phenyl(C1-Cs)alkyl (wherein the phenyl is optionally substituted
`
`by 1, 2 or 3 of, independently, C,-Csalkyl, C,-Csfluoroalkyl, C;:-C3alkoxy, C.-Csfluoroalkoxy,
`
`30
`
`C,-Czalkylthio, C,-Cgalkylsulfinyl, C;-C3 alkylsulfonyl, halogen, cyano or nitro), heteroaryl(C,-
`
`Cs)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C,-
`
`Caalkyl, C1-Csfluoroalkyl, C1-Csalkoxy, C.1-Csfluoroalkoxy, C.-Csalkylthio, C1-Csalkylsulfinyl,
`
`C,-C3 alkylsulfonyl, halogen, cyano or nitro), phenoxy(C,-Cs)alkyl (wherein the phenyl
`
`is
`
`optionally substituted by 1, 2 or 3 of,
`
`independently, C,-Csalkyl, C,-Cefluoroalkyl, C,-
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`-11-
`
`Czalkoxy, C1-Csfluoroalkoxy, C,-Cgalkylthio, C,-Cgalkylsulfinyl, C;-C3 alkylsulfonyl, halogen,
`
`cyano or nitro), heteroaryloxy(C,-Cs)alkyl (wherein the heteroaryl is optionally substituted by
`
`1,2 or 3 of, independently, C,-Czalkyl, C;-Csfluoroalkyl, C;-Csalkoxy, C,-C3fluoroalkoxy, C,-
`
`Cgalkylthio, C,-Czalkylsulfinyl, C;-C3
`
`alkylsulfonyl,
`
`halogen,
`
`cyano
`
`or
`
`nitro),
`
`Cs-
`
`Csflucroalkenyl, C3-Cecycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently,
`
`C,-Caalkyl, C1-Csfluoroalkyl, C.-Csalkoxy, C.1-Csfluoroalkoxy, halogen,
`
`cyano or nitro;
`
`heteroaryl or heteroaryl substituted by 1, 2 or 3 of,
`
`independently, C,-Csalkyl, C,-
`
`Czfluoroalkyl, C1-Cgalkoxy, C,-Csfluoroalkoxy, halogen, cyano or nitro; C,-Cgalkyl-C(O)-; or
`
`phenyl-C(O)- wherein the phenyl is optionally substituted by 1 or 2 of, independently, C,-
`
`10
`
`Czalkyl, C,fluoroalkyl, C;-Czalkoxy, C,fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro;
`
`wherein “heteroaryl" means an aromatic ring system containing at least one ring heteroatom
`
`and consisting either of a single ring or of two fused rings;
`
`15
`
`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 |, each alkyl moiety either
`
`alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl, alkylcarbonyl,
`
`20
`
`alkylaminocarbonyl, or dialkylaminocarbonyl, et al.) can be straight-chained or branched.
`
`Typically,
`
`the alkyl
`
`is, for example, methyl, ethyl, n-propyl,
`
`isopropyl, n-butyl, sec-butyl,
`
`isobutyl, tert-butyl, n-pentyl, neopentyl, or n-hexyl. The alkyl groups can e.g. be C,-Cealkyl
`
`groups (except where already defined more narrowly), but are preferably C,)-C,alkyl or C,-
`
`Cz3alkyl groups
`
`(except where already defined more narrowly), and, more preferably, are
`
`25
`
`C,-Czalkyl groups such as methyl.
`
`Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the
`
`alkenyl moieties, where appropriate, can be of either the (£)- or (Z)-configuration. The
`
`alkenyl or alkynyl are typically C2z-Csalkenyl or C2-Czalkynyl such as vinyl, allyl, ethynyl,
`
`30
`
`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).
`
`

`

`WO 2015/197468
`
`PCT/EP2015/063744
`
`-12-
`
`Halogenis fluorine, chlorine, bromine or iodine. Preferred halogens arefluorine, 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 C1-Czfluoroalkyl or
`
`C,-Cofluoroalkyl (preferably C,fluoroalkyl), such as CF3, CHF2, CHeaF, CH3CHF-, CF3CH2-,
`
`CHF2CH2-, CH2FCH2-, CHF2CF2- or (CH3)2CF-.
`
`Fluoroalkoxy is typically C,-C3fluoroalkoxy
`
`or C,-C2fluoroalkoxy (preferably C,fluoroalkoxy), such as CF30, CHF20, CH2FO, CH3CHFO-,