Substituted isoxazoline derivatives

A compound of formula I

• wherein
• R1 is C1-C2-haloalkyl;
• W is phenyl, or 5- or 6-membered heteroaryl comprising as ring members 1, 2, or 3 heteroatoms selected from N, O, and S;
• wherein W is unsubstituted, partially or fully substituted with R2;
• R2 is halogen, OR21, NR22R23, CN, NO2, Si(CH3)3, SbF5, C1-C4-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C1-C3-alkyl-S(O)m, C1-C3-haloalkyl-S(O)m, C1-C3-alkoxy-C1-C4-alkyl, C1-C3-haloalkoxy-C1-C4-alkyl, C1-C3-alkyl-S(O)m—C1-C4-alkyl, C1-C3-haloalkyl-S(O)mC1-C4-alkyl, C3-C6-cyclo¬alkyl, C3-C6-halocyclo¬alkyl;
• which groups are optionally substituted with R211;
• m is 0, 1, or 2;
• R21 H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C4-alkyl-S(O)m, Si(C1-C4-alkyl)3, which groups are unsubstituted, or partially or fully substituted with R211;
• R211 halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C4-alkenyloxy, C3-C4-haloalkenyloxy, C3-C4-alkynyloxy, C3-C4-haloalkynyloxy, C1-C4-alkyl-S(O)m, C1-C4-haloalkyl-S(O)m, C3-C4-alkenyl-S(O)m, C3-C4-haloalkenyl-S(O)m, C3-C4-alkynyl-S(O)m, C3-C4-haloalkynyl-S(O)m, and oxo;
• C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl;
• R22, R23 H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, which are unsubstituted, or partially or fully substituted with R221;
• or
• C1-C6-alkyl-C(═O)OR13, C1-C6-alkyl-C(═U)N(R12a)R12b, C1-C6-alkyl-C(═NR12)N(R12a)R12b,
• S(O)mR13, S(O)mN(R12a)R12b, C(═U)R11, C(═O)OR13, C(═U)N(R12a)R12b, C(═S)SR13, C(═NR12)R11;
• C3-C8-cycloalkyl, C3-C8-halocycloalkyl;
• R221 CN, NO2, OH, SH, SCN, SF5, Si(C1-C4-alkyl)3, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyl-S(O)m, C1-C6-haloalkyl-S(O)m, C(═O)N(R12a)R12b;
• C3-C8-cycloalkyl which is unsubstituted, or partially or fully halogenated and/or partially or fully substituted with C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• or
• two R221 present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group may together be ═O, ═CH(C1-C4-alkyl), ═C(C1-C4-alkyl)2, ═N(C1-C6-alkyl), or ═NO(C1-C6-alkyl);
• or
• R22 and R23 form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, or 6-membered fully unsaturated heterocycle, which heterocycle optionally can contain one heteroatom selected from N, O, and S(O)m as ring members, and which heterocycle is unsubstituted or partially or fully substituted with R14;
• or
• R22 and R23 together form a group ═C(R11)2, ═S(O)m(R13)2, ═S(O)mR13N(R12a)R12b;
• X is NR3, O, S(O)m, or CH2;
• R3 is OR21, or a group as defined for R5;
• G is phenyl, or a 5- or 6-membered heteroaryl comprising as ring members 1, 2, or 3 heteroatoms selected from N, O and S;
• wherein G is unsubstituted, or partially or fully substituted with R4;
• R4 is a group as defined for R2;
• U is O or S;
• R5 is H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, which are unsubstituted, or partially or fully substituted with R51;
• or
• C1-C6-alkyl-C(═O)OR13, C1-C6-alkyl-C(═U)N(R12a)R12b, C1-C6-alkyl-C(═NR12)N(R12a)R12b, N(R12a)R12b, S(O)mR13, S(O)mN(R12a)R12b, C(═U)R11, C(═O)OR13, C(═U)N(R12a)R12b C(═S)SR13, C(═NR12)R11;
• C3-C8-cycloalkyl, C3-C8-halocycloalkyl, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated or partially unsaturated heterocycle comprising 1, 2, 3 or 4 heteroatoms selected from N, O, and S(O)m as ring members, or a 5- or 6-membered hetaryl comprising 1, 2, 3 or 4 heteroatoms selected from N, O, and S(O)m as ring members, which rings are unsubstituted, or partially or fully substituted with R52;
• R51 halogen, CN, NO2, OH, SH, SCN, SF5, Si(C1-C4-alkyl)3, N(R12a)R12b, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyl-S(O)m, C1-C6-haloalkyl-S(O)m, C(═O)N(R12a)R12b;
• C3-C8-cycloalkyl which is unsubstituted, or partially or fully halogenated and/or partially or fully substituted with CN, C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• N(R12a)R12b, S(O)mR13, S(O)mN(R12a)R12b, C(═U)R11, C(═O)OR13, C(═U)N(R12a)R12b, C(═S)SR13, C(═NR12)R11;
• phenyl, benzyl, phenoxy, or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocycle containing 1, 2, or 3 heteroatoms selected from N, O, S(O)m as ring members, wherein the rings are unsubstituted, or partially or fully substituted with R14;
• or
• two R51 present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group may together be ═O, ═CH(C1-C4-alkyl), ═C(C1-C4-alkyl)2, ═N(C1-C6-alkyl), or ═NO(C1-C6-alkyl);
• R52 is a group as defined in R51 or selected from C1-C6-alkyl, C2-C6-alkenyl, and C2-C6-alkynyl, which groups are unsubstituted, or partially or fully halogenated and/or substituted with one or two CN, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, or oxo;
• R6 is a group as defined for R5;
• or
• R5 and R6 form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, or partially or fully unsaturated heterocycle which heterocycle optionally can contain one or two heteroatoms selected from N, O, and S(O)m as ring members, and which heterocycle is unsubstituted, or partially or fully substituted with R14;
• or
• R5 and R6 together form a group ═C(R11)2, ═S(O)m(R13)2, ═S(O)mN(R12a)R12b, ═NR12, or ═NOR13;
• or
• R5 and R6 together with the nitrogen they are bound to form a mesoionic entity;
• Y having at G one or two ring atoms of G between connection points of G to X and Y;
• Y being a direct bond or CR7R8;
• R7, R8 are each independently selected from H, halogen, CN, C1-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, and C2-C6-alkynyl, which groups may be partially or fully halogenated and/or may be substituted by one or more R81;
• R81 is CN, N3, NO2, SCN, SF5, C3-C8-cycloalkyl, C3-C8-halocycloalkyl;
• Si(C1-C4-alkyl)3, OR13, OSO2R13, S(O)mR13, NR22R23, C(═O)NR22R23;
• or
• R7 and R8, together with the carbon atom they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocycle or heterocycle, wherein the heterocycle comprises 1, 2, 3, or 4 heteroatoms or heteroatom groups independently selected from N, O, and S(O)m as ring members, which rings are unsubstituted or substituted with 1 or 2 groups R14;
• R11 is CN, NO2, OH, SH, SCN, SF5, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyl-S(O)m, C1-C6-haloalkyl-S(O)m, Si(C1-C4-alkyl)3, C(═O)N(R12a)R12b,
• C3-C8-cycloalkyl which is unsubstituted, or partially or fully halogenated and/or substituted with 1 or 2 C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• phenyl, benzyl, phenoxy, a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocycle containing 1, 2, or 3 heteroatoms N, O, and S(O)m as ring members, which rings are unsubstituted, or partially or fully halogenated and/or substituted with R14;
• or
• two R11 present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl may together form ═O, ═CH(C1-C4-alkyl), ═C(C1-C4-alkyl)C1-C4-alkyl, ═N(C1-C6-alkyl), or ═NO(C1-C6-alkyl);
• and
• R11 bonded to a cycloalkyl ring is additionally C1-C6-alkyl, C2-C6-alkenyl, and C2-C6-alkynyl, which are unsubstituted, or partially or fully halogenated and/or substituted with 1 or 2 groups CN, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• and
• R11 in groups ═C(R11)2, N═C(R11)2, C(═U)R11, and C(═NR12)R11 is additionally selected from H, halogen, C1-C6-alkyl, C2-C6-alkenyl, and C2-C6-alkynyl, which are unsubstituted, or partially or fully halogenated and/or substituted with 1 or 2 groups CN, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• R12 is H, C1-C6-alkoxy, C1-C6-haloalkoxy, S(O)m—C1-C4-alkyl, S(O)m—C1-C4-haloalkyl, Si(C1-C4-alkyl)3, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, which are unsubstituted, or partially or fully halogenated and/or substituted with CN, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)m—C1-C4-alkyl, S(O)m—C1-C4-haloalkyl, C3-C6-cycloalkyl which is unsubstituted or substituted with 1 or 2 halogen and/or CN;
• and oxo;
• C3-C8-cycloalkyl which is unsubstituted, or partially or fully halogenated and/or substituted with CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C4-cycloalkyl, C3-C4-cycloalkyl-C1-C4-alkyl which rings optionally are substituted with 1 or 2 halogen and/or CN;
• and oxo;
• phenyl, benzyl, pyridyl, phenoxy, which are unsubstituted, or partially or fully halogenated and/or substituted with halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and (C1-C6-alkoxy)carbonyl;
• and a 3-, 4-, 5- or 6-membered saturated, partially or fully unsaturated heterocycle comprising 1, 2, or 3 heteroatoms selected from N, O, and S(O)m as ring members, where the heterocycle is optionally substituted with one or more R14;
• R12a and R12b have the meanings given for R12;
• or
• R12a and R12b, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, or partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring optionally can contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, and S(O)m as ring members, which heterocycle is unsubstituted or substituted with one or more substituents halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• or
• R12a and R12, together with the nitrogen atoms to which they are bound in the group C(═NR12)N(R12a)R12b, form a 3-, 4-, 5-, 6- or 7-membered saturated, or partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring optionally can contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, and S(O)m as ring members, which heterocycle is unsubstituted or substituted with one or more substituents halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, and oxo;
• R13 is H, Si(C1-C4-alkyl)3, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which are unsubstituted, or partially or fully halogenated and/or substituted with C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)m—C1-C4-alkyl, and oxo;
• C3-C8-cycloalkyl which is unsubstituted, or partially or fully halogenated and/or substituted with C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)m—C1-C4-alkyl, and oxo;
• phenyl, benzyl, pyridyl and phenoxy, which are unsubstituted, or partially or fully halogenated and/or substituted with C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, and (C1-C6-alkoxy)carbonyl;
• R14 is halogen, NO2, CN, OH, SH, C1-C6-alkoxy, C1-C6-haloalkoxy, S(O)m—C1-C4-alkyl, S(O)mC1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C(═O)NR12aR12b, Si(C1-C4-alkyl)3;
• C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which are unsubstituted, or partially or fully halogenated and/or substituted with C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)mC1-C4-alkyl, and oxo;
• C3-C8-cycloalkyl which is unsubstituted, or partially or fully halogenated and/or substituted with C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)m—C1-C4-alkyl, and oxo;
• phenyl, benzyl, pyridyl and phenoxy, which are unsubstituted, or partially or fully halogenated and/or substituted with C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, and (C1-C6-alkoxy)carbonyl;
• or
• two R14 present together on the same atom of an unsaturated, or partially unsaturated ring may be ═O, ═S, ═N(C1-C6-alkyl), ═NO(C1-C6-alkyl), ═CH(C1-C4-alkyl) or ═C(C1-C4-alkyl)C1-C4-alkyl;
• or
• two R14 on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring optionally can contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, and S(O)m as ring members, and wherein the ring is optionally substituted with one or more groups C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and/or C1-C4-haloalkoxy;
• and N-oxides, stereoisomers and agriculturally or veterinarily acceptable salts thereof.