Herbicidally active (alkynyl-phenyl)-substituted cyclic dione compounds and derivatives thereof

A compound of formula (I):

• wherein:
• X is methyl or chlorine;
• R1 is fluorine or bromine;
• R2 is ethynyl, C1-C3alkoxy-, C1-C3haloalkoxy-, or C1-C3alkoxy-C1-C3alkoxy-;
• and
• Q is a group of either formula Q1 or Q2:
• wherein:
• R3, R4 and R5, independently of each other, are hydrogen, C1-C5alkyl, C2-C4 alkenyl, C2-C4alkynyl, C1-C2fluoroalkyl or C1-C3alkoxyC1-C3alkyl;
• R6 is hydrogen, C1-C5alkyl, C2-C4alkenyl, C2-C4alkynyl, R6AA—C≡C—CH2—, C1-C2fluoroalkyl, C1-C3alkoxyC1-C3alkyl, C1-C3alkylthioC1-C3alkyl, C1-C3alkylsulfinylC1-C3alkyl, C1-C3alkyl-sulfonylC1-C3alkyl, C3-C4cycloalkyl, or an unsubstituted 4-, 5- or 6-membered monocyclic heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and nitrogen, and attached at a ring carbon atom within the heterocyclyl,
• or R6 is T-(CH2)m—CH(R7)—, wherein m is 0 or 1 and either R7 is hydrogen or R7 and R5 together are a bond, and T is an optionally substituted heterocyclyl as defined below;
• or R6 is Het-CH(R8)—, wherein either R8 is hydrogen or R8 and R5 together are a bond, and Het is an optionally substituted heteroaryl as defined below;
• or R6 is C3-C6cycloalkylC1-C2alkyl-;
• or is C4-C6cycloalkylC1-C2alkyl-, substituted at a cycloalkyl ring-carbon atom which is not the ring-carbon atom attached to the —C1-C2alkyl- moiety and which is not bonded directly to the ring-carbon atom attached to the —C1-C2alkyl- moiety, by one or two ring substituents which independently are:
• ═N—O—R10, oxo (═O), C1-C4alkoxy, C1-C2haloalkoxy, 2-(C1-C3alkoxy)-ethoxy, C3-C5cycloalkyloxy, (C3-C5cycloalkyl)methoxy, C2-C3alkenyl-CH2-oxy, C1-C3alkyl or C1-C2fluoroalkyl;
• or benzyloxy in which the phenyl ring is optionally substituted by one or two substituents independently being C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)—, —C(O)—N(R6H)(R6J), SR6E, S(O)R6E, —S(O)2—R6E, —N(R6F)(R6G), hydroxy, C2-C3alkenyl, —C(R6BB)═(R6C1)(R6C2), C2-C3alkynyl, —C≡C—R6AA, C1-C3alkoxy, C1-C2fluoroalkoxy, cyclopropyloxy, CH2═CH—CH2—O—, HC≡C—CH2—O—, halogen, cyano or nitro;
• or R6 is benzyl optionally substituted on its phenyl ring by one or two substituents which independently are:
• C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)—, —C(O)—N(R6H)(R6J), SR6E, S(O)R6E, S(O)2R6E, —S(O)2—R6E, —N(R6F)(R6G), hydroxy, C2-C3alkenyl, —C(R6BB)═C(R6C1)(R6C2), C2-C3alkynyl, —C≡C—R6AA, C1-C3alkoxy, C1-C2fluoroalkoxy, cyclopropyloxy, CH2═CH—CH2—O—, HC≡C—CH2—O—, halogen, cyano or nitro;
• or R3 and R4 taken together are —(CH2)n1— or —(CH2)n2—X1—(CH2)n3— and R5 and R6 are as defined above,
• or R5 and R6 taken together are —(CH2)n1— or —(CH2)n2—X1—(CH2)n3— and R3 and R4 are as defined above
• or R4 and R6 taken together are
• —C(R11)(R12)—C(R13)(R14)—C(R15)(R16)—C(R17)(R18)—, —C(R11)(R12)—C(R13)═C(R15)—C(R17)(R18)—, or —CH(R19)—C(R20)(R21)—CH(R22)—;
• and
• T is a 4 to 7 membered monocyclic- or an 8 to 11 membered fused bicyclic- heterocyclyl, having one or two ring heteroatoms independently selected from oxygen, sulfur and nitrogen;
• and wherein T is optionally substituted by 1 or 2 ring-carbon substituents independently being C1-C3alkyl, C1-C2fluoroalkyl, —SC1-C3alkyl, —S(O)C1-C3alkyl, —S(O)2C1-C3alkyl, or oxo (═O), and/or is optionally substituted by one C1-C4alkyl, C1-C2fluoroalkyl, C1-C4alkoxy, C1-C2fluoroalkoxy;
• or a R9—C(O)—, or a C1-C2alkyl-S(O)2— substituent on a ring nitrogen if present, and/or is optionally substituted by one or two oxo (═O) substituents on a ring sulfur if present;
• Het is a heteroaryl, attached at a ring-carbon, which is optionally substituted by 1, 2 or 3 ring-carbon substituents independently being C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)—, —C(O)—N(R6H)(R6J), SR6E, S(O)R6E, S(O)2R6E, —S(O)2—R6E, —N(R6F)(R6G), hydroxy, C2-C3alkenyl, —C(R6BB)═(R6C1)(R6C2), C2-C3alkynyl, —C≡C—R6AA, C1-C3alkoxy, C1-C2fluoroalkoxy, cyclopropyloxy, CH2═CH—CH2—O—, HC≡C—CH2—O—, halogen, cyano or nitro;
• and/or, in the case of a 5-membered heteroaryl ring containing a ring-nitrogen atom not partaking in a C═N ring double bond, the heteroaryl is optionally substituted on the ring-nitrogen atom not partaking in a C═N ring double bond by one C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)— or C1-C2alkyl-S(O)2— substituent;
• wherein:
• R6AA is C1fluoroalkyl, fluorine, chlorine or bromine;
• R6B, R6C and R6CC independently are hydrogen, methyl, C1fluoroalkyl, fluorine or chlorine;
• provided that R6B, R6C and R6CC in total contain no more than one carbon atom, and R6B, R6C and R6CC in total comprise no more than one chlorine;
• R6BB, R6C1 and R6C2 independently are hydrogen, methyl, C1fluoroalkyl, 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;
• R6D and R6E independently are C1-C3alkyl, C1fluoroalkyl, or —N(R6H)(R6J);
• R6F is C1-C2alkyl, —C(O)—C1fluoroalkyl, —S(O)2—C1-C2alkyl, —S(O)2-C1fluoroalkyl, C1-C2alkyl, or C1fluoroalkyl;
• R6G and R6J independently are hydrogen, methyl or C1fluoroalkyl;
• and
• R6H is hydrogen, C1-C2alkyl, or C1fluoroalkyl;
• and
• R9 is C1-C4alkyl, C2-C4alkenyl attached at a carbon atom partaking in the C═C double bond, C1-C2fluoroalkyl, C1-C2alkoxymethyl-, C1-C3alkoxy, cyclopropyl, furanyl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, pyrazol-5-yl, 3-methylpyrazol-5-yl, 1-methylpyrazol-5-yl, 1,3-dimethylpyrazol-5-yl;
• or phenyl or phenyl substituted by 1 or 2 substituents independently being methyl, ethyl, C1fluoroalkyl, methoxy, C1fluoroalkoxy, fluorine, chlorine, SC1-C3alkyl, S(O)C1-C3alkyl, or S(O)2C1-C3alkyl;
• R10 is hydrogen, C1-C4alkyl, C1-C2fluoroalkyl, 2-(C1-C3alkoxy)-ethyl, C3-C5cycloalkyl or (C3-C5cycloalkyl)methyl;
• X1 is O, S, S(O), S(O)2, NH, N(C1-C3alkyl), N(C1-C3alkoxy), C(H)(C1-C2alkyl), C(C1-C2alkyl)2, C(H)(C1-C3alkoxy) or C(Me)(C1-C2alkoxy);
• n1 is 2, 3, 4 or 5;
• and n2 and n3 are independently 1, 2 or 3 provided that n2+n3 is 2, 3 or 4;
• R11 and R18 are both hydrogen, or R11 and R18 are taken together and form an —O— or —C1-C2alkylene- bridge;
• and
• R12 and R17 are independently hydrogen, C1-C3alkyl or C1-C2alkoxyC1-C2alkyl;
• R13, R14 and R15 are independently hydrogen, C1-C3alkyl or C1-C2alkoxyC1-C2alkyl, provided that one, two or all of R13, R14 and R15 are hydrogen;
• R16 is hydrogen;
• C1-C3alkyl;
• C1-C2alkoxyC1-C2alkyl;
• phenyl optionally substituted by 1, 2 or 3 of, independently, C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)—, —C(O)—N(R6H)(R6J), SR6E, S(O)R6E, S(O)2R6E, —S(O)2—R6E, —N(R6F)(R6G) hydroxy, C2-C3alkenyl, —C(R6BB)═C(R6C1)(R6C2), C2-C3alkynyl, —C≡C—R6AA, C1-C3alkoxy, C1-C2fluoroalkoxy, cyclopropyloxy, CH2═CH—CH2—O—, HC≡C—CH2—O—, halogen, cyano or nitro;
• or a 5-membered or 6-membered heteroaryl, attached at a ring-carbon and optionally substituted by 1, 2 or 3 ring-carbon substituents independently being C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)—, —C(O)—N(R6H)(R6J), SR6E, S(O)R6E, S(O)2R6E, —S(O)2—R6E, —N(R6F)(R6G), hydroxy, C2-C3alkenyl, —C(R6BB)═C(R6C1)(R6C2), C2-C3alkynyl, —C≡C—R6AA, C1-C3alkoxy, C1-C2fluoroalkoxy, cyclopropyloxy, CH2═CH—CH2—O—, HC≡C—CH2—O—, halogen, cyano or nitro;
• R19 and R22 are independently hydrogen, C1-C3alkyl or C1-C2alkoxyC1-C2alkyl;
• and R20 and R21 are independently hydrogen, C1-C3alkyl or C1-C2alkoxyC1-C2alkyl;
• or R20 and R21 taken together are oxo (═O), ═N—O—R10, or ═CH2;
• or R20 and R21, together with the carbon atom to which they are attached, form a 5, 6 or 7 membered saturated heterocyclyl, wherein the heterocyclyl has two ring heteroatoms independently being oxygen or sulfur and which are not directly bonded to each other, and wherein the heterocyclyl is optionally substituted by 1, 2 or 3 ring-carbon substituents independently being C1-C2alkyl;
• and wherein in Q2:
• R33, R34, R35 and R36, independently of each other, are hydrogen, C1-C5alkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C2fluoroalkyl, C1-C3alkoxyC1-C3alkyl, C1-C3alkylthioC1-C3alkyl, C1-C3alkylsulfinylC1-C3alkyl, C1-C3alkylsulfonylC1-C3alkyl, C3-C4cycloalkyl, or an unsubstituted 4, 5 or 6 membered monocyclic heterocyclyl having one ring heteroatom independently selected from oxygen, sulfur and nitrogen, said heterocyclyl being attached at a ring carbon atom within the heterocyclyl;
• provided that no more than one of R33, R34, R35 and R36 is alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkyl or heterocyclyl;
• or R33 and R34 taken together are —(CH2)n31— or —(CH2)n32—X31—(CH2)n33— and R35 and R36 are as defined above, or R35 and R36 taken together are —(CH2)n31— or —(CH2)n32—X1—(CH2)n33— and R33 and R34 are as defined above;
• X31 is O, S, S(O), S(O)2, NH, N(C1-C2alkyl), N(C1-C2alkoxy), C(H)(C1-C2alkyl), C(C1-C2alkyl)2 or C(H)(C1-C2alkoxy);
• n31 is 2, 3, 4 or 5;
• n32 and n33 are independently 1, 2 or 3 provided that n32+n33 is 2, 3 or 4;
• Y is O, S, S(O), S(O)2, N(C1-C2alkyl), N(C1-C2alkoxy), C(O), CR38R39 or —CR310R311CR312R313—;
• and
• R38 and R39 are, independently of each other:
• hydrogen, C1-C6alkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C2fluoroalkyl, C1-C3alkoxyC1-C3alkyl, C1-C3alkylthioC1-C3alkyl, C1-C3alkylsulfinylC1-C3alkyl, or C1-C3alkylsulfonylC1-C3alkyl;
• C3-C6cycloalkyl or C3-C6cycloalkyl substituted by one or two substituents which independently are C1-C3alkyl or C1-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(O)2, NH, N(C1-C3alkyl), N(C1-C2fluoroalkyl), N[C(O)C1-C3alkyl], N[C(O)C1-C2fluoroalkyl] or N(C1-C2alkoxy) moiety;
• C3-C6cycloalkyl substituted by one substituent being C1-C3alkoxy and optionally further substituted by one substituent being C1-C2alkyl;
• C5-C6cycloalkenyl or C5-C6cycloalkenyl substituted by one or two C1-C3alkyl substituents;
• C3-C6cycloalkylC1-C2alkyl- or C3-C6cycloalkylC1-C2alkyl- substituted by one or two ring substituents which independently are C1-C3alkyl or C1-C2fluoroalkyl, and in which one ring CH2 moiety of a C4-C6cycloalkylC1-C2alkyl- is optionally replaced by an oxygen or sulfur atom or by a S(O), S(O)2, NH, N(C1-C2alkyl), N(C1-C2fluoroalkyl), N[C(O)C1-C3alkyl], N[C(O)C1-C2fluoroalkyl] or N(C1-C2alkoxy) moiety;
• C3-C6cycloalkylC1-C2alkyl- substituted by one ring substituent being C1-C3alkoxy and optionally further substituted by one ring substituent being C1-C2alkyl;
• or HetA or HetA-CH2—;
• wherein HetA is a heteroaryl, attached at a ring-carbon, which is optionally substituted by 1, 2 or 3 ring-carbon substituents independently being C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)—, —C(O)—N(R6H)(R6J), SR6E, S(O)R6E, —S(O)2—R6E, —N(R6F)(R6G), hydroxy, C2-C3alkenyl, —C(R6BB)═C(R6C1)(R6C2), C2-C3alkynyl, —C≡C—R6AA, C1-C3alkoxy, C1-C2fluoroalkoxy, cyclopropyloxy, CH2═CH—CH2—O—, HC≡C—CH2—O—, halogen, cyano or nitro;
• and/or, in the case of a 5-membered heteroaryl ring containing a ring-nitrogen atom not partaking in a C═N ring double bond, the heteroaryl is optionally substituted on the ring-nitrogen atom not partaking in a C═N ring double bond by one C1-C3alkyl, C1-C2fluoroalkyl, C1-C3alkyl-C(O)—, C1-C2fluoroalkyl-C(O)— or C1-C2alkyl-S(O)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(O)2, NH, N(C1-C3alkyl), N(C1-C2fluoroalkyl), N[C(O)C1-C3alkyl], N[C(O)C1-C2fluoroalkyl] or N(C1-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(O)2, NH, N(C1-C3alkyl), N(C1-C2fluoroalkyl), N[C(O)C1-C3alkyl], N[C(O)C1-C2fluoroalkyl] or N(C1-C2alkoxy) moiety, or HetA or HetA-CH2—;
• or R38 is hydrogen or C1-C2alkyl, and R39 is C1-C2alkoxy;
• or R38 and R39 taken together are —(CH2)n37— or —(CH2)n38—X32—(CH2)n39—;
• wherein X32 is O, S, S(O), S(O)2, NH, N(C1-C3alkyl), N(C1-C2fluoroalkyl), N[C(O)C1-C3alkyl], N[C(O)C1-C2fluoroalkyl], N(C1-C2alkoxy), C(H)(C1-C3alkyl), C(C1-C2alkyl)2 or C(H)(C1-C3alkoxy);
• n37 is 2, 3, 4, 5 or 6;
• and
• n38 and n39 are independently 0, 1, 2 or 3 provided that n38+n39 is 2, 3, 4 or 5;
• and
• R310, R311, R312 and R313 are independently of each other hydrogen or C1-C4alkyl provided that no more than one of R310, R311, R312 and R313 is C3-C4alkyl;
• and wherein R6AA, R6BB, R6C1, R6C2, R6E, R6F, R6G, R6H and R6J are as defined hereinabove for when Q is Q1;
• and
• and wherein:
• G is hydrogen, an agriculturally acceptable metal, or an agriculturally acceptable sulfonium or ammonium group;
• or
• G is —C(Xa)—Ra, —C(Xb)—Xc—Rb, —C(Xd)—N(Rc)—Rd, —SO2—Re, —P(Xe)(Rf)—Rg, —CH2—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-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)-;
• Xa, Xb, Xc, Xd, Xe and Xf are independently of each other oxygen or sulfur;
• 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, 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), 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), 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;
• 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, 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 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(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 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 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)—;
• 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;
• 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 or a tautomer thereof.