Process for Preparing Amidrazones

A process for preparing amidrazones of formula I or a salt thereof

• wherein
• R is hydrogen;
• R1 is C1-C10-alkyl;
• R2 is C3-C10-cycloalkyl which is unsubstituted or substituted with 1 to 5 halogen atoms and/or 1 to 3 C1-C6-alkyl groups and/or 1 to 3 C1-C6-haloalkyl groups;
• A is C—R3 or N;
• B is C—R4 or N;
• W is C—R5 or N;
• with the proviso that one of A, B and W is other than N;
• R3, R4, R5 are each independently hydrogen, halogen, nitro, cyano, amino, mercapto, hydroxy, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)-amino, C1-C6-alkylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl or a 5- to 6-membered aromatic ring which may contain 1 to 4 hetero-atoms selected from oxygen, sulfur and nitrogen;
• Y is hydrogen, halogen, cyano, nitro, amino, hydroxy, mercapto, C1-C6-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6)-alkylamino, C1-C6-alkylthio, C1-C6-alkylsulfonyl, or C1-C6-alkylsulfinyl;
• and
• n is 0, 1, or 2,
• comprising reacting an arylhydrazine of formula II
• wherein R, A, B, W, Y and n are each as defined above,
• with an imidoyl compound of formula III
• wherein R1 and R2 are each as defined above and X1 is halogen, C1-C6-alkoxy, C1-C6-alkylsulfonate, C1-C6-haloalkylsulfonate, C6-C12-arylsulfonate, Cl-C6-alkylthio, C1-C6-alkylphosphate, or C6-C12-arylphosphate, optionally in the presence of a base.

An imidoyl compound of formula III

• wherein
• R1 is C1-C10-alkyl, C3-C10-alkenyl, C3-C10-alkynyl, C3-C12-cycloalkyl, di(C1-C6-alkyl)-amino, C1-C6-alkylsulfonyl or C1-C6-alkylsulfinyl, wherein in each of the above radicals the alkyl, alkenyl, alkynyl or cycloalkyl groups are unsubstituted or substituted with 1 to 3 substituents independently selected from the group consisting of halogen, nitro, cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-haloalkylsulfinyl, C3-C6-cycloalkyl, phenyl and pyridyl;
• R2 is cyclopropyl which is substituted with 1 to 3 halogen atoms and/or 1 to 3 C1-C6-alkyl groups and/or 1 to 3 C1-C6-haloalkyl groups;
• and
• X1 is halogen, C1-C6-alkoxy, C1-C6-alkylsulfonate, C1-C6-haloalkylsulfonate, C6-C12-arylsulfonate, C1-C6-alkylthio, C1-C6-alkylphosphate, or C6-C12-arylphosphate.

An amide of formula IV

• wherein
• R1 is C1-C10-alkyl, C3-C10-alkenyl, C3-C10-alkynyl, C3-C12-cycloalkyl, di(C1-C6-alkyl)-amino, C1-C6-alkylsulfonyl, or C1-C6-alkylsulfinyl, wherein in each of the above radicals the alkyl, alkenyl, alkynyl or cycloalkyl groups are unsubstituted or substituted with 1 to 3 substituents independently selected from the group consisting of halogen, nitro, cyano, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-haloalkylsulfinyl, C3-C6-cycloalkyl, phenyl and pyridyl;
• and
• R2 is a cyclopropyl group of formula VII as defined above wherein R6 is C1-C6 alkyl, R7 and R8 are both chlorine, and R9 and R10 are both hydrogen.