US 9,808,003 B2
Herbicidally active 2-(substituted-phenyl)-cyclopentane-1,3-dione compounds and derivatives thereof
Alaric James Avery, Bracknell (GB); John Benjamin Taylor, Bracknell (GB); Russell Colin Viner, Bracknell (GB); Jeffery Steven Wailes, Bracknell (GB); Ian Stuart Cloudsdale, Chapel Hill, NC (US); John Kenneth Dickson, Jr., Chapel Hill, NC (US); Ian Henry Aspinall, Bracknell (GB); Janice Black, Bracknell (GB); Emma Briggs, Bracknell (GB); Shuji Hachisu, Bracknell (GB); and Simon Hardy, Bracknell (GB)
Assigned to Syngenta Limited, Guildford, Surrey (GB)
Appl. No. 14/785,470
Filed by Syngenta Limited, Guildford, Surrey (GB)
PCT Filed Apr. 16, 2014, PCT No. PCT/EP2014/057835
§ 371(c)(1), (2) Date Oct. 19, 2015,
PCT Pub. No. WO2014/170413, PCT Pub. Date Oct. 23, 2014.
Claims priority of application No. 1307093.3 (GB), filed on Apr. 19, 2013; and application No. 1310115.9 (GB), filed on Jun. 6, 2013.
Prior Publication US 2016/0081334 A1, Mar. 24, 2016
Int. Cl. A01N 37/18 (2006.01); A01N 37/40 (2006.01); A01N 43/00 (2006.01); C07C 233/00 (2006.01); C07C 235/46 (2006.01); C07D 213/81 (2006.01); C07D 213/82 (2006.01); C07D 215/48 (2006.01); C07D 237/24 (2006.01); C07D 239/52 (2006.01); C07D 241/24 (2006.01); C07D 307/68 (2006.01); C07D 333/38 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); A01N 43/40 (2006.01); C07D 231/14 (2006.01); C07D 231/56 (2006.01); C07D 233/90 (2006.01); C07D 239/28 (2006.01); C07D 471/04 (2006.01); C07C 233/76 (2006.01); C07D 207/46 (2006.01); C07D 277/56 (2006.01); A01N 25/32 (2006.01); A01N 43/08 (2006.01); A01N 43/10 (2006.01); A01N 43/16 (2006.01); A01N 43/38 (2006.01); A01N 43/42 (2006.01); A01N 43/52 (2006.01); A01N 43/54 (2006.01); A01N 43/56 (2006.01); A01N 43/58 (2006.01); A01N 43/60 (2006.01); A01N 43/76 (2006.01); A01N 43/78 (2006.01); A01N 43/80 (2006.01); A01N 43/82 (2006.01); A01N 47/06 (2006.01); C07C 233/31 (2006.01); C07C 233/32 (2006.01); C07C 235/60 (2006.01); C07C 233/61 (2006.01)
CPC A01N 37/18 (2013.01) [A01N 25/32 (2013.01); A01N 37/40 (2013.01); A01N 43/08 (2013.01); A01N 43/10 (2013.01); A01N 43/16 (2013.01); A01N 43/38 (2013.01); A01N 43/40 (2013.01); A01N 43/42 (2013.01); A01N 43/52 (2013.01); A01N 43/54 (2013.01); A01N 43/56 (2013.01); A01N 43/58 (2013.01); A01N 43/60 (2013.01); A01N 43/76 (2013.01); A01N 43/78 (2013.01); A01N 43/80 (2013.01); A01N 43/82 (2013.01); A01N 47/06 (2013.01); C07C 233/31 (2013.01); C07C 233/32 (2013.01); C07C 233/61 (2013.01); C07C 233/76 (2013.01); C07C 235/46 (2013.01); C07C 235/60 (2013.01); C07D 207/46 (2013.01); C07D 213/81 (2013.01); C07D 213/82 (2013.01); C07D 215/48 (2013.01); C07D 231/14 (2013.01); C07D 231/56 (2013.01); C07D 233/90 (2013.01); C07D 237/24 (2013.01); C07D 239/28 (2013.01); C07D 239/52 (2013.01); C07D 241/24 (2013.01); C07D 277/56 (2013.01); C07D 307/68 (2013.01); C07D 333/38 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 471/04 (2013.01); C07C 2601/04 (2017.05); C07C 2601/08 (2017.05); C07C 2601/14 (2017.05)] 21 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Drawing
wherein:
R1 is methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine,chlorine, bromine, methoxy, ethoxy or fluoromethoxy;
R2 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, fluoroethyl, vinyl, prop-1-enyl, ethynyl, prop-1-ynyl, 2-chloroethynyl, 2-fluoroethynyl, 2-(trifluoromethyl)ethynyl, but-1-ynyl, 2-(cyclopropyl)ethynyl, halogen, methoxy, prop-2-ynyloxy,
or (C1-C2 fluoroalkyl)-methoxy-;
or R2 is phenyl optionally substituted by 1, 2 or 3 of, independently, halogen, C1-C2alkyl, C1-C2fluoroalkyl, C1-C2alkoxy, C1-C2fluoroalkoxy, cyano or nitro;
or R2 is monocyclic heteroaryl optionally substituted by 1, 2 or 3 of independently,halogen, C1-C2alkyl, C1-C2fluoroalkyl, C1-C2alkoxy, C1-C2fluoroalkoxy, cyano or nitro;
or R2 is

OG Complex Work Unit Drawing
 in which R36 is fluorine or chlorine, and R37 is fluorine, chlorine or C1fluoroalkyl; and
R3 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy, n-propoxy, isopropoxy, C1-C2fluoroalkoxy, C1-C2alkoxy-C1-C3alkoxy-, or C1fluoroalkoxy-C1-C3alkoxy-;
R4, R5 and R6, independently of each other, are hydrogen, C1-C5alkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C2fluoroalkyl or C1-C2alkoxyC1-C2alkyl;
provided that: either (i) at least two of R4, R5 and R6 are hydrogen, or (ii) two of R4, R5 and R6 are methyl and the remaining one of R4, R5 and R6 is hydrogen; and
R7 and R8, independently of each other, are hydrogen, fluorine or C1-C3alkyl; and
R9 and R10, independently of each other, are hydrogen, fluorine or C1-C3alkyl;
provided that no more than two of R7, R8, R9 and R10 are fluorine;
and provided that at least two of R7, R8, R9 and R10 are hydrogen;
and wherein
R11 is C1-C6alkyl, C3-C7cycloalkyl, tetrahydro-2H-pyranyl, tetrahydrofuranyl, oxetanyl, tetrahydrothiophene-yl or thietanyl;
or R11 is a monocyclic 6-membered-ring heteroaryl, which is carbon-linked, and which is pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl or 1,2,4-triazinyl, wherein the monocyclic 6-membered-ring heteroarylisoptionally substituted by 1, 2 or 3 substituents;
wherein the 1, 2 or 3 optional substituents on the monocyclic 6-membered-ring heteroaryl independently are fluorine, chlorine, bromine, iodine, C1-C3alkyl, C1-C3fluoro alkyl, C1-C2alkoxy C1-C2fluoroalkoxy, cyclopropyl, Cn1alkoxyCn2alkyl (wherein n1 is 1 or 2, n2 is 1 or 2, and n1+n2 is 2 or 3), vinyl, C2fluoroalkenyl, C2-C3alkynyl, fluoroethynyl, cyano, amino, or phenyl in which the phenyl is optionally substituted at its meta and/or para position(s) by 1 or 2 fluorines; and
wherein, when R11 is pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl or 1,2,4-triazinyl, then each of these is optionally substituted by 1 or 2 of the substituents on the monocyclic 6-membered-ring heteroaryl, as defined herein;
wherein, when R11 is pyridin-3-yl or pyridin-4-yl, then each of these is substituted by 1 or 2 of the substituents on the monocyclic 6-membered-ring heteroaryl, as defined herein,
wherein, when R11 is pyridin-2-yl substituted by 3 substituents, then one or more of the optional substituents on the pyridin-2-yl is or are fluorine;
wherein, when R11 is monocyclic 6-membered-ring heteroaryl substituted by C2alkyl, C2fluoroalkyl, C2alkoxy or C2fluoroalkoxy, then: the monocyclic 6-membered-ring heteroaryl is substituted by 1 or 2 substituents independently being C2alkyl, C2fluoroalkyl, C2alkoxy or C2fluoroalkoxy, and the monocyclic 6-membered-ring heteroaryl is optionally further substituted by 1 or 2 substituents independently being fluorine, chlorine, bromine, C1alkyl, C1fluoroalkyl, C1alkoxy, C1fluoroalkoxy or cyano; provided that the monocyclic 6-membered-ring heteroaryl is substituted by no more than 2 substituents or in the case of a pyridin-2-yl is substituted by no more than 3 substituents;
wherein, when R11 is monocyclic 6-membered-ring heteroaryl substituted by iodine, C3alkyl, C3fluoroalkyl, cyclopropyl, Cn1alkoxyCn2alkyl, vinyl, C2fluoroalkenyl, C2-C3alkynyl or fluoroethynyl, then: the monocyclic 6-membered-ring heteroaryl is pyridin-2-yl substituted by only one iodine, C3alkyl, C3fluoroalkyl, cyclopropyl, Cn1alkoxyCn2alkyl, vinyl, C2fluoroalkenyl, C2-C3alkynyl or fluoroethynyl, and in which the pyridin-2-yl ring is optionally further substituted by 1 or 2 fluorines;
wherein, when R11 is monocyclic 6-membered-ring heteroaryl substituted by amino, then: either the monocyclic 6-membered-ring heteroaryl is 6-amino-pyridin-2-yl optionally further substituted by 1 or 2 fluorines; or the monocyclic 6-membered-ring heteroaryl is 3-amino-pyridin-2-yl or 3-amino-pyrazin-2-yl each of which is optionally further substituted at the 5-position of the pyridin-2-yl or pyrazin-2-yl ring by hydrogen, fluorine, methyl or C1fluoroalkyl; and
wherein, when R11 is monocyclic 6-membered-ring heteroaryl substituted by optionally substituted phenyl, then the monocyclic 6-membered-ring heteroaryl is 6-phenyl-pyridin-2-yl in which the phenyl is optionally substituted at its meta and/or para position(s) by 1 or 2 fluorines, and in which the pyridin-2-yl ring is optionally further substituted by 1 or 2 fluorines;
or R11 is a monocyclic 5-membered-ring heteroaryl, which is carbon-linked, and which is pyrrolyl, pyrazolyl, imidazol-2-yl, triazolyl, tetrazolyl, furyl, thiophenyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, or thiadiazolyl, wherein the monocyclic 5-membered-ring heteroaryl is optionally substituted by 1, 2 or 3 substituents;
wherein the 1, 2 or 3 optional substituents on the monocyclic 5-membered-ring heteroaryl are:
1, 2 or 3 optional ring-carbon substituents independently being fluorine, chlorine, bromine, C1-C3alkyl, C1-C3fluoroalkyl, C1-C2alkoxy, C1-C2fluoroalkoxy, cyclopropyl, Cn3alkoxyCn4alkyl (wherein n3 is 1 or 2, n4 is 1 or 2, and n3+n4 is 2 or 3), vinyl, C2fluoroalkenyl, C2-C3alkynyl, fluoroethynyl or cyano; and/or
1 substituent being C1-C3alkyl, C1-C3fluoroalkyl or cyclopropyl, substituted at a ring nitrogen not partaking in a double bond, when the monocyclic 5-membered-ring heteroaryl has a ring nitrogen not partaking in a double bond;
provided that the monocyclic 5-membered-ring heteroaryl has no more than 3 substituents, or has no more than the maximum number of substituents possible for the monocyclic 5-membered-ring heteroaryl in uncharged form if this maximum is less than 3 substituents; and
wherein, when R11 is a monocyclic 5-membered-ring heteroaryl having a ring nitrogen not partaking in a double bond, then the ring nitrogen not partaking in a double bond is substituted by C1-C3alkyl, C1-C3fluoroalkyl or cyclopropyl; and
wherein, when R11 is a monocyclic 5-membered-ring heteroaryl, then: the monocyclic 5-membered-ring heteroaryl has no more than one C3fluoroalkyl, vinyl, C2fluoroalkenyl, C2-C3alkynyl or fluoroethynyl substituent; the monocyclic 5-membered-ring heteroaryl has no more than 2 substituents independently being bromine, C2-C3alkyl, C2-C3fluoroalkyl, C1-C2alkoxy, C1-C2fluoroalkoxy, cyclopropyl, Cn3alkoxyCn4alkyl, vinyl, C2fluoroalkenyl, C2-C3alkynyl, fluoroethynyl or cyano; and the monocyclic 5-membered-ring heteroaryl has no more than 2 substituents independently being chlorine or bromine;
or R11 is one of the following sub-formulae B, E, F, GG, H, J, Q, R, S, T or U:

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
wherein:
XB is nitrogen or CR13B;
YB is nitrogen or CR14B;
ZB is nitrogen or CR15B;
provided that no more than one of XB, YB and ZB is nitrogen; and
R12B is hydrogen, fluorine, chlorine or bromine;
R13B is hydrogen, fluorine, chlorine, bromine, methyl, C1fluoroalkyl, cyano, methoxy or C1fluoroalkoxy;
R14B is hydrogen, fluorine or chlorine;
R15B is hydrogen, fluorine, chlorine or bromine;
provided that at least two of R12B, R13B, R14B and R15B are hydrogen;
and provided that, when R13B is bromine, then XA is CR13B, and R12B, R14B and R15B are independently hydrogen or fluorine, provided that at least two of R12B, R14B and R15B are hydrogen; and
R15E is hydrogen, fluorine or chlorine;
R12F is hydrogen, fluorine or chlorine;
R11GG is hydrogen, fluorine, methyl or C1fluoroalkyl;
R12GG is hydrogen, fluorine or chlorine;
R13GG is hydrogen, fluorine, chlorine, bromine, C1fluoroalkyl, methoxy or C1fluoroalkoxy;
R14GG is hydrogen or fluorine;
R15GG is hydrogen, fluorine, chlorine, methoxy or C1fluoroalkoxy;
provided that, when R13GG is bromine, then R11GG, R12GG, R14GG and R15GG are independently hydrogen or fluorine;
provided that, when R11GG is methyl or C1fluoroalkyl, then R12GG, R13GG, R14GG and R15GG are independently hydrogen or fluorine; and
provided that at least two of R12GG, R13GG, R14GG and R15GG are hydrogen; and
R26 is hydrogen or methyl;
R27 is hydrogen or methyl;
R28 and R29 independently are hydrogen or fluorine;
R12T, R13T and R14T are independently hydrogen or fluorine, provided that at least two of R12T, R13T and R14T are hydrogen; and
R12U, R13U and R14U are independently hydrogen or fluorine, provided that at least two of R12U, R13U and R14U are hydrogen;
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, —SO2—Re, —P(Xe)(Rf)—Rg, —CH2—Xf—Rh, or —CH(Me)-Xf—Rh; or phenyl-CH2— or phenyl-CH(C1-C2alkyl)- (in each of which the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C2alkyl, C1fluoroalkyl, C1-C2alkoxy, C1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or heteroaryl-CH2— or heteroaryl-CH(C1-C2alkyl)- (in each of which the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C2alkyl, C1fluoroalkyl, C1-C2alkoxy, C1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro), or phenyl-C(O)—CH2— (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C2alkyl, C1fluoroalkyl, C1-C2alkoxy, C1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro); or C1-C6alkoxy-C(O)—CH2—, C1-C6alkyl-C(O)—CH2—, C1-C6alkoxy-C(O)—CH═CH—, C2-C7alken-1-yl-CH2—, C2-C7alken-1-yl-CH(C1-C2alkyl)-, C2-C4fluoroalken-1-yl-CH2—, C2-C7alkyn-1-yl-CH2—, or C2-C7alkyn-1-yl-CH(C1-C2alkyl)-;
wherein Xa, Xb, Xc, Xd, Xe and Xf are independently of each other oxygen or sulfur; and wherein
Ra is H, C1-C21alkyl, C2-C21alkenyl, C2-C18alkynyl, C1-C10fluoroalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino(C1-C5)alkyl, C2-C8dialkylamino(C1-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, C1-C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C1-C5alkylcarbonyl(C1-C5)alkyl, C1-C5alkoxycarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, C1-C5alkylaminocarbonyl (C1-C5)alkyl, C2-C8dialkylaminocarbonyl(C1-C5)alkyl, C1-C5alkylcarbonylamino(C1-C5)alkyl, N—(C1-C5)alkylcarbonyl-N—(C1-C5)alkylamino(C1-C5)alkyl, C3-C6trialkylsilyl(C1-C5)alkyl, phenyl(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C1-C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro;
Rb is C1-C18alkyl, C3-C18alkenyl, C3-C18alkynyl, C2-C10fluoroalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C2-C10aminoalkyl, C1-C5alkylamino(C1-C5)alkyl, C2-C8dialkylamino(C1-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, C1-C5alkylsulfonyl (C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C1-C5alkylcarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, C1-C5alkylaminocarbonyl(C1-C5)alkyl, C2-C8dialkylaminocarbonyl(C1-C5)alkyl, C1-C5alkylcarbonylamino(C1-C5)alkyl, N—(C1-C5)alkylcarbonyl-N—(C1-C5)alkylamino(C1-C5)alkyl, C3-C6trialkylsilyl(C1-C5)alkyl, phenyl(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; and
Rc and Rd are each independently of each other hydrogen, C1-C10alkyl, C3-C10alkenyl, C3-C10alkynyl, C2-C10fluoroalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino (C1-C5)alkyl, C2-C8dialkylamino(C1-C5)alkyl, C3-C7cycloalkyl(C1-C5)alkyl, C1-C5alkoxy(C1-C5)alkyl, C3-C5alkenyloxy(C1-C5)alkyl, C3C5alkynyloxy(C1-C5)alkyl, C1-C5alkylthio(C1-C5)alkyl, C1-C5alkylsulfinyl(C1-C5)alkyl, C1-C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C1C5alkylcarbonyl(C1-C5)alkyl, C1-C5alkoxycarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, C1-C5alkylaminocarbonyl(C1-C5)alkyl, C2-C8dialkylaminocarbonyl(C1-C5)alkyl, C1-C5alkylcarbonylamino(C1-C5)alkyl, N—(C1-C5)alkylcarbonyl-N—(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(C1-C5)alkyl, phenyl(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C1-C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di (C3C7cycloalkyl)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 or S; and
Re is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10fluoroalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino(C1-C5)alkyl, C2-C8dialkylamino(C1-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, C1-C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C1-C5alkylcarbonyl(C1-C5)alkyl, C1-C5alkoxycarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, C1-C5alkylaminocarbonyl(C1-C5)alkyl, C2-C8dialkylaminocarbonyl(C1-C5)alkyl, C1-C5alkylcarbonylamino(C1-C5)alkyl, N—(C1-C5)alkylcarbonyl-N—(C1-C5)alkylamino(C1-C5)alkyl, C3-C6trialkylsilyl(C1-C5)alkyl, phenyl(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C1-C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di(C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, C1-C10alkoxy, C1-C10fluoroalkoxy, C1-C5alkylamino or di(C1-C4alkyl)amino;
Rf and Rg are each independently of each other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10alkoxy, C1-C10fluoroalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino(C1-C5)alkyl, C2-C8dialkylamino(C1-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, C1-C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C1-C5alkylcarbonyl(C1-C5)alkyl, C1-C5alkoxycarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, C1-C5alkylaminocarbonyl(C1-C5)alkyl, C2-C8dialkylaminocarbonyl(C1-C5)alkyl, C1-C5alkylcarbonylamino(C1-C5)alkyl, N—(C1-C5)alkylcarbonyl-N—(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(C1-C5)alkyl, phenyl(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), heteroaryl(C1-C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or nitro), C2-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; or C3-C7cycloalkylamino, di(C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, C1-C10fluoroalkoxy, C1-C5alkylamino or di(C1-C4alkyl)amino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; and
Rh is C1-C10alkyl, C3-C10alkenyl, C3-C10alkynyl, C1-C10fluoroalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C2-C10aminoalkyl, C1-C5alkylamino(C1-C5)alkyl, C2-C8dialkylamino(C1-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, C1-C5alkylsulfonyl(C1-C5)alkyl, C2-C8alkylideneaminoxy(C1-C5)alkyl, C1-C5alkylcarbonyl(C1-C5)alkyl, C1-C5alkoxycarbonyl(C1-C5)alkyl, aminocarbonyl(C1-C5)alkyl, C1-C5alkylaminocarbonyl(C1-C5)alkyl, C2-C8dialkylaminocarbonyl(C1-C5)alkyl, C1-C5alkylcarbonylamino(C1-C5)alkyl, N—(C1-C5)alkylcarbonyl-N—(C1-C5)alkylamino(C1-C5)alkyl, C3-C6trialkylsilyl(C1-C5)alkyl, phenyl(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano or nitro), heteroaryl(C1-C5)alkyl(wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano or nitro), phenoxy(C1-C5)alkyl (wherein the phenyl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano or nitro), heteroaryloxy(C1-C5)alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano or nitro), C3-C5fluoroalkenyl, C3-C8cycloalkyl; phenyl or phenyl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, halogen, cyano or nitro; C1-C6alkyl-C(O)—; C1-C6alkoxy-C(O)—; or phenyl-C(O)— wherein the phenyl is optionally substituted by 1 or 2 of, independently, C1-C2alkyl, C1fluoroalkyl, C1-C2alkoxy, C1fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro;
wherein “heteroaryl” means an aromatic ring system containing at least one ring heteroatom and consisting either of a single ring or of two fused rings;
and wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof.