Parasiticide formulations suitable for dermal application

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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A01N 4340

Patent

active

060018585

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to formulations for the dermal control of parasitic insects on animals by means of agonists or antagonists of the nicotinergic acetylcholine receptors of insects.
Agonists or antagonists of the nicotinergic acetylcholine receptors of insects are known. They include the nicotinyl insecticides and, very particularly, the chloronicotinyl insecticides.
PCT application WO 93/24 002 discloses that certain 1-[N-(halo-3-pyridylmethyl)]-N-methylanino-1-alkylamino-2-nitroethylene derivatives are suitable for systemic use against fleas in domestic animals. According to WO 93/24 002, the nonsysternic--i.e. dermal--mode of application is unsuitable for the control of fleas on domestic animals.
New formulations for the dermal application of agonists or antagonists of the nicotinergic acetylcholine receptors of insects have now been found which are particularly suitable for dermal control of parasitic insects, such as fleas, lice or flies, on animals.
The formulations according to the invention have the following composition: insects in a concentration of from 1 to 20% by weight based on the overall weight of the formulation; pyrrolidones in a concentration of at least 20% by weight based on the overall weight of the formulation; or lactones in a concentration of from 5.0 up to 80% by weight based on the overall weight of the formulation; agents, colorants, antioxidants, propellants, preservatives, adhesives, emulsifiers, in a concentration of from 0.025 up to 10% by weight based on the overall weight of the formulation.
Agonists or antagonists of the nicotinergic acetylcholine receptors of insects are known, for example, from European Offenlegungsschriften (European Published Applications) Nos. 464 830, 428 941, 425 978, 386 565, 383 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136 636, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 302 389; German Offenlegungsschriften (Gerrnan Published Specifications) Nos. 3 639 877, 3 712 307; Japanese Offenlegungsschriften (Japanese Published Applications) Nos. 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072, U.S. Pat. Nos. 5,034,524, 4,948,798, 4,918,086, 5,039,686, 5,034,404; PCT Applications Nos. WO 91/17 659, 91/4965; French Application No. 2 611 114; Brazilian Application No. 88 03 621.
Express reference is hereby made to the compounds described in these publications and to their preparation.
These compounds can be represented preferably by the general formula (I) ##STR1## in which R represents, hydrogen, optionally substituted radicals from the group acyl, alkyl, aryl, aralkyl, heteroaryl or heteroarylalkyl; aryl, or represents a bifinctional group which is linked to the radical Z; radical --CH.dbd. instead of a H-atom to be linked to the radical Z; ##STR2## or represents a bifunctional group which is linked to the radical A or to the radical X.
Particularly preferred compounds of the formula (I) are those in which the radicals have the following meaning: the series acyl, alkyl, aryl, aralkyl, heteroaryl, heteroarylalkyl. arylcarbonyl, alkylsulphony, arylsulphonyl, (alkyl)-(aryl)-phosphoryl, which may in turn be substituted. -alkyl, specifically methyl, ethyl, i-propyl, sec- or t-butyl, which may in turn be substituted. and N, O, S especially N as heteroatoms. Specifically there may be mentioned thienyl, furyl, thiazolyl, imidazolyl, pyridyl, benzothiazolyl, heteroarylethyl having up to 6 ring atoms and N, O, S, especially N as heteroatoms. alkyl having preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methyl, ethyl, n- and i-propyl and n-, i- and t-butyl; alkoxy having preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and n-, i- and t-butyloxy; alkylthio having preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methylthio, ethylthio, n- and i-propylthio and n-, i- and t-butylthio; halogenoalkyl having preferably 1 to 4, in particular 1 or 2 carbon atoms and preferably

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