Hydrazone derivatives, processes for production thereof, and uses thereof

An agricultural and horticultural insecticide comprising as an active ingredient a hydrazone derivative represented by the general formula (I):

• ##STR16## wherein each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms;
• A represents --N.dbd.C(R.sup.4)-- or --NH--CH(R.sup.4)-- (wherein R.sup.4 represents a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms);
• X, which may be the same or different, represents a halogen atom, nitro group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, or an alkylsulfonyl group having 1 to 5 carbon atoms;
• Y, which may be the same or different, represents a halogen atom, cyano group, nitro group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, an alkylsulfonyl group having 1 to 5 carbon atoms, a haloalkylthio group having 1 to 5 carbon atoms, a haloalkylsulfinyl group having 1 to 5 carbon atoms, a haloalkylsulfonyl group having 1 to 5 carbon atoms, an alkynyl group having 2 to 5 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;
• Z, which may be the same or different, represents a halogen atom, nitro group, cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, a haloalkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, a haloalkylsulfinyl group having 1 to 5 carbon atoms, an alkylsulfonyl group having 1 to 5 carbon atoms, a haloalkylsulfonyl group having 1 to 5 carbon toms, a haloalkylsulfonyloxy group having 1 to 5 carbon atoms, an alkylcarbonyl group having 1 to 5 carbon atoms, or phenoxy group;
• l, m and n each represents 0 or an integer of 1 to 5, said compound containing at least one cyano group.

A method for controlling undesirable insect pests which comprises treating useful crops with an agricultural and horticultural insecticide comprising as an active ingredient a hydrazone derivative represented by the general formula (I):

• ##STR17## wherein each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms;
• A represents --N.dbd.C(R.sup.4)-- or --NH--CH(R.sup.4)-- (wherein R.sup.4 represents a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms);
• X, which may be the same or different, represents a halogen atom, nitro group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, or an alkylsulfonyl group having 1 to 5 carbon atoms;
• Y, which may be the same or different, represents a halogen atom, cyano group, nitro group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, an alkylsulfonyl group having 1 to 5 carbon atoms, a haloalkylthio group having 1 to 5 carbon atoms, a haloalkylsulfinyl group having 1 to 5 carbon atoms, a haloalkylsulfonyl group having 1 to 5 carbon atoms, an alkynyl group having 2 to 5 carbon atoms, or an alkoxycarbonyl group having 1 to 5 carbon atoms;
• Z, which may be the same or different, represents a halogen atom, nitro group, cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, a haloalkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, a haloalkylsulfinyl group having 1 to 5 carbon atoms, an alkylsulfonyl group having 1 to 5 carbon atoms, a haloalkylsulfonyl group having 1 to 5 carbon atoms, a haloalkylsulfonyloxy group having 1 to 5 carbon atoms, an alkylcarbonyl group having 1 to 5 carbon atoms, or phenoxy group;
• l, m and n each represents 0 or an integer of 1 to 5, said compound containing at least one cyano group in the range of 1 g to 5 kg (in terms of the active ingredient) per 10 ares, thereby to prevent useful crops from injurous insect pests.

A method for controlling according to claim, 10, wherein in the general formula (I), each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms;

• A represents --N.dbd.C(R.sup.4)-- or --NH--CH(R.sup.4)-- (wherein R.sup.4 represents a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms);
• X, which may be the same or different, represents a halogen atom, an alkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms;
• Y, which may be the same or different, represents cyano group, nitro group, or a haloalkylsulfinyl group having 1 to 5 carbon atoms;
• Z, which may be the same or different, represents a halogen atom, a haloalkyl group having 1 to 5 carbon atoms, or a haloalkoxy group having 1 to 5 carbon atoms;
• l, m and n each represents an integer of 1 to 3.