Pesticidal activity of functionalized cyclopropanes

A method of initiating a TMOF receptor-mediated biological response, comprising contacting to a TMOF receptor in vivo or in vitro for a time and in an amount sufficient to initiate a TMOF receptor-mediated biological response a compound selected from the group consisting of compounds of formula I, and salt, acid and ester forms thereof:

• 10
• wherein:
• X is cyclopropyl;
• Z is selected from the group consisting of —OH, —NH2, —NHR6 and —OR6 wherein R6 is alkyl, alkenyl, optionally substituted cycloalkylalkyl, and optionally substituted aralkyl;
• m≧0 and n≧1 and (m+n) can have any integer value from 1 to 12 inclusive;
• the ring bearing substituents R1, R2, R3, R4 and R5 is a phenyl ring or a cyclohexyl ring, or a corresponding ring wherein one or more ring carbon atom(s) has been replaced by nitrogen atom(s);
• R1, R2, R3, R4, and R5 are each independently selected from the group consisting of —H, —OH, halo, loweralkyl, loweralkoxy, nitro, amino, and phenyl;
• subject to the proviso that:
• when the ring is a phenyl ring, a pair of R1 and R2, R2 and R3, or R3 and R4 on the phenyl ring may together represent —CR7═CR8—CR9═CR10—, to form with the phenyl ring illustrated above a naphthyl ring system, wherein R7, R8, R9, and R10 are each independently selected from the group consisting of —H, —OH, halo, nitro, amino, loweralkyl, and loweralkoxy.

A pest control composition comprising a pesticidal carrier and a pesticidal compound selected from the group consisting of compounds of formula I, and salt, acid and ester forms thereof:

• 14
• wherein:
• X is cyclopropyl;
• Z is selected from the group consisting of —OH, —NH2, —NHR6 and —OR6 wherein R6 is alkyl, alkenyl, optionally substituted cycloalkylalkyl, and optionally substituted aralkyl;
• m≧0 and n≧1 and (m+n) can have any integer value from 1 to 12 inclusive;
• the ring bearing substituents R1, R2, R3, R4 and R5 is a phenyl ring or a cyclohexyl ring, or a corresponding ring wherein one or more ring carbon atom(s) has been replaced by nitrogen atom(s);
• R1, R2, R3, R4, and R5 are each independently selected from the group consisting of —H, —OH, halo, loweralkyl, loweralkoxy, nitro, amino, and phenyl;
• subject to the proviso that:
• when the ring is a phenyl ring, a pair of R1 and R2, R2 and R3, or R3 and R4 on the phenyl ring may together represent —CR7═CR8—CR9═CR10—, to form with the phenyl ring illustrated above a naphthyl ring system, wherein R7, R8, R9, and R10 are each independently selected from the group consisting of —H, —OH, halo, nitro, amino, loweralkyl, and loweralkoxy.

A compound selected from the group consisting of compounds of

• 18
• wherein:
• X is cyclopropyl;
• Z is selected from the group consisting of —OH, —NH2, —NHR6 and —OR6 wherein R6 is alkyl, alkenyl, optionally substituted cycloalkylalkyl, and optionally substituted aralkyl;
• m≧0 and n≧1 and together total an integer from 1 to 12;
• the ring bearing substituents R1, R2, R3, R4 and R5 is a phenyl ring or a cyclohexyl ring, or a corresponding ring wherein one or more ring carbon atom(s) has been replaced by nitrogen atom(s);
• R1, R2, R3, R4, and R5 are each independently selected from the group consisting of —H, —OH, halo, loweralkyl, loweralkoxy, nitro, amino, and phenyl;
• subject to the proviso that:
• when the ring is a phenyl ring, a pair of R1 and R2, R2 and R3, or R3 and R4 on the phenyl ring may together represent —CR7═CR8—CR9═CR10—, to form with the phenyl ring illustrated above a naphthyl ring system, wherein R7, R8, R9, and R10 are each independently selected from the group consisting of —H, —OH, halo, nitro, amino, loweralkyl, and loweralkoxy.