Oxy-cope rearrangement for the manufacture of insecticidal cyclopentene compounds

A compound of formula I

• wherein
• R1 is halomethyl;
• R2 is halogen, halomethyl, or halomethoxy;
• R3, R4 are independently H, or as defined for R2;
• R5a is H, C1-C4-alkyl, or C1-C4-haloalkyl;
• R5b is CN, halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy;
• or
• R5a and R5b form together with the C-atoms they are bound to a 5-, or 6-membered saturated, partially, or fully unsaturated ring containing none, or one heteroatom O, N(O)n or S(O)m as ring members;
• A is halogen, CN, C1-C6-alkoxy, C6-C10-aryloxy, C1-C6-haloalkoxy, C6-C10-arylalkoxy, C6-C10-aryl-C1-C6-alkoxy, OS(O)2R6;
• or
• a group A1, or A2;
• wherein
• A1 is a group of following formula:
• wherein
• # denotes the attachment point to the remainder of the molecule;
• Y OR7, or N(R8)R9;
• and
• A2 is a group of following formula:
• wherein
• # denotes the attachment point to the remainder of the molecule;
• R6 halogen, C1-C6-alkyl, C1-C6-haloalkyl;
• phenyl, which is unsubstituted, or substituted by halogen, OH, CN, NO2, C1-C6-alkyl, or C1-C6-haloalkyl;
• R7 a) H;
• b) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl;
• or
• c) phenyl, or benzyl, which are unsubstituted, or substituted by halogen, C1-C2-alkyl, C1-C2-haloalkyl, or C1-C2-alkoxy;
• R8 H, CN;
• C1-C6-alkyl-C(═O), C1-C6-haloalkyl-C(═O), C1-C6-alkyl-OC(═O), C1-C6-alkenyl-OC(═O), or C6-C12-aryl-C1-C6-alkyl-OC(═O);
• C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, which are unsubstituted or substituted by R81;
• R81 halogen, CN, N3, NO2, SCN, SF5, C3-C8-cycloalkyl, C3-C8 halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkoxy, or C3-C8-halocycloalkoxy;
• R9 H;
• C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which are unsubstituted, or substituted by R91;
• C3-C6-cycloalkyl, C3-C6-halocycloalkyl, which are unsubstituted, or substituted by R92;
• N(R93)R94;
• phenyl, heterocyclyl, or hetaryl, which are unsubstituted, or substituted by RD;
• or
• C1-C6-alkyl-C(═O), C1-C6-haloalkyl-C(═O), C1-C6-alkyl-OC(═O), C1-C6-alkenyl-OC(═O), or C6-C12-aryl-C1-C6-alkyl-OC(═O);
• R91 halogen, OH, CN, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O)m, C1-C4-haloalkyl-S(O)m, C(═O)N(RA)RB;
• C3-C6-cycloalkyl, C3-C6-halocycloalkyl, which are unsubstituted, or substituted by RC;
• phenyl, heterocyclyl, or hetaryl which are unsubstituted, or substituted by RD;
• RA, R93 H, C1-C3-alkyl, or C1-C3-haloalkyl;
• RB H, C1-C3-alkyl, C1-C3-haloalkyl, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C2-C3-haloalkynyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C3-C4-halocycloalkyl;
• or
• C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-halocycloalkylmethyl, wherein the cyclic groups are unsubstituted, or substituted by CN;
• RC OH, CN, C1-C2-alkyl, or C1-C2-haloalkyl;
• RD halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C4-cycloalkylmethyl, or C3-C4-halocycloalkylmethyl;
• or
• two RD present on the same carbon atom of a saturated, or partially saturated ring form together a carbonyl group (═O);
• R92 C1-C2-alkyl, C1-C2-haloalkyl, or a group as defined for R91;
• R94 C(═O)N(RA)RB, C(═O)ORA;
• or
• phenyl, heterocyclyl, or hetaryl which rings are unsubstituted, or substituted by RD;
• R10 H, CN, methyl, or halomethyl;
• R11 H, C1-C6-alkyl-C(═O), C1-C6-haloalkyl-C(═O), C1-C6-alkyl-OC(═O), C1-C6-alkenyl-OC(═O), or C6-C12-aryl-C1-C6-alkyl-OC(═O);
• R12 H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which are unsubstituted, or substituted by R91;
• C3-C6-cycloalkyl, C3-C6-halocycloalkyl, which are unsubstituted, or substituted by R92;
• or
• phenyl, heterocycyl, or hetaryl which rings are unsubstituted, or substituted by RD;
• n is 0, or 1;
• m is 0, 1, or 2;
• and the N-oxides, stereoisomers and agriculturally or veterinarily acceptable salts thereof.