DE2013788A1 - Aryl isothiocyanate miticides - Google Patents

Abstract

Ectoparasiticidal agents, esp. for combatting Sarcoptidae on animals, e.g. Psoroptes cuniculi on rabbits, and P. ovis on sheep, contain a cpd. of formula (I): (where R is lower alkyl, alkoxy or alkylthio, trihalomethyl, R1OCO-, R2R3NCO-, halogen, NO2 and/or CN; n is 1-5; R1 is a (cyclo)aliphatic gp.; R2 and R3 = H, and/or lower aliphatic gps.) and opt. extenders and/or surfactants.

Description

Ectoyarasiticidal Agents The present invention relates to use of aromatic isothiocyanates for combating ectoparasites in veterinary medicine, especially of mange mites.

It is already known that the γ-isomer of Hexachlorcyclo = hexane can be used as a smear mite agent. However, this preparation has the Disadvantage that it penetrates through the skin and into the body of the treated animals is stored there in the fat as a non-degradable polychloride compound (cf. Mathysse, J. G., W. H. Gutenmann, R. Gigger, Sheep Ectoparasite Control. II. Toxicity to Sheep, and Residues of Diazinon and Lindane, Journ. Econom. Entomol. 61, 207-209; All sup, T. N., M. H. Wharton, Gamma Benzene Hexachloride (Gamma BHC) Toxicity in Calves, Vet. Rec. 80, 583-584; It is also known that isothiocyanates are used in veterinary medicine can be used to combat endoparasites.

For example, 1,4-phenylene-bis-isothiocyanate has a Action against hookworms, tapeworms and roundworms (see German patent specification 1 172 664).

It has now been found that aromatic isothiocyanates of the formula (I) in which R stands for lower alkyl, alkoxy, alkylmercapto, trihalomethyl, Halogen, nitro and / or cyano and n stands for 1 to 5, where R1 is an aliphatic or cycloaliphatic radical, R2 and R are hydrogen and / or lower aliphatic radicals, are highly effective against ectoparasites, especially dust mites.

It is extremely surprising that the invention to be used Connections are characterized by a high permanent effect and in the application do not react with water or other substances (e.g. wool).

The compounds to be used in the present invention are represented by the above Formula (I) generally uniquely characterized.

Here, however, R preferably stands for methyl, methoxy, methyl mercapto, Trifluoromethyl, a lower alkoxy carbonyl or alkyl amide radical, chlorine, bromine, Nitro and / or cyano.

n preferably has the value 1 to 3. R1 preferably represents one lower aliphatic radical with 1 to 4 carbon atoms, which is optionally replaced by alkoxy, Alkylmercapto or alkylamino radicals can be substituted, or a cycloaliphatic one Remainder with 5 to 6 ring carbon atoms. R2 and R3 are preferably hydrogen and aliphatic Residues with 1 to 4 carbon atoms.

The active ingredients to be used in the present invention are partial as such already described in the literature and accessible by known methods, see 3. from the corresponding aromatic primary amines by reaction with thiophosgene (See. Houben-Weyl, "Methods of Organic Chemistry", 4th Edition, Volume IX, page 875 LT955J) or from aromatic Isocyanide dichlorides and sodium sulfide or phosphorus pentasulfide (Angew. Chem., Volume 81, page 18 [1969]).

Among other things, they are particularly suitable for combating the B mites the following compounds: 2,6-dichloro, 2,3,5,6-tetrachloro-4-nitro-, 2,6-dichloro-4-cyano-, 2,6-dibromo-4-nitro-, 2,3,5,6-tetrachloro-, 4-meth = oxycarbonyl-, 3-ethoxycarbonyl-, 2-methoxycarbonyl-, 2-isopropoxycarbonyl-, 3-isobutoxycarbonyl-, 4-n-butoxy = carbonyl-, 4-liloxycarbonyl-, 4-propargoxycarbonyl-, 4-N, N'-diethylaminoethoxycarbonyl-, 4- (2-ethoxyethoxycarbonyl) -, 4- (2-ethylmercaptoethoxycarbonyl), 4-cyclohexoxycarbonyl, 3-cyclopentoxycarbonyl, 2,5-bis (methoxycarbonyl) -, 3-chloro-6-methoxycarbonyl-, 4-chloro-6-ethoxycarbonyl-, 3,5-bisethoxycarbonyl-, 2-methoxy-5-methoxycarbonyl-, 4-methyl-5-ethoxycarbonyl-, 3-carbonamido, 4-N, N-diethylcarbonamido, 2-N-allylcarbonamino, 4-trifluoromethyl-2-methoxycarbonyl = phenyl isothiocyanate.

As already mentioned, the products to be used according to the invention are on the veterinary sector with success against ectoparasites especially the Order Acarida used.

The following ectoparasites on animals may be mentioned from this order: Sarcoptidae, such as the rabbit sucking mite (Psoroptes cuniculi) and the sheep sucking mite (Psoroptes ovis).

The new means are used in a known manner dermal application in the form of dipping (dip), spraying (spray), pouring (pour-on, Spot-on) and powdering (dusting).

Example 1: Suction mite test / Psoroptes cuniculi solvent: 35 Parts by weight of ethylene glycol monomethyl ether 35 parts by weight of nonylphenol polyglycol ether Test procedure: Transfer of 10-25 specimens of the test animals for each concentration tested in filter paper sandwiches impregnated with active ingredient (diameter 7.5 cm). Manufacturing of the sandwiches by pipetting on 3 ml of the concentration to be tested. After that 'overpass and storage in the air-conditioned test room.

Effect check after 24 hours.

Criteria: The occurrence of death in the counts as an impact criterion treated mites.

Valuation: 100% effect = all Mites are > 50% effect = more than 50% # killed, <50% effect = less than 50% 0% effect = all mites are alive.

The active ingredients examined, the concentrations tested and the results obtained are shown in Table 1 below: Table 1 Active ingredient active ingredient kill rate (Constitution) concentration in in ppm after 24 hours NCS 300 100 Cl to Cl 100 100 b / I 30 (50 10 0 300 100 100 100 5CNC00CH3 3 100 - 3 10 100 3 100 1 0 NCS 300 100 C00C2H5 30 100 3 2 5 100 NCS Cl 4 Cl 300 100 Cl 4 C1 30 ° NO2 Cl 300 100 NC <NCS 100> 50 '30> 50 Ol 10 0 10.

Continuation of table 1 le 1 Active ingredient active ingredient degree of killing (Constitution) concentration ino in ppm after 24 hours 300 100 02N <NCS 30 <50 3 3 0 Br NCS NCS Br to r 300 100 30 0 Cl NCS 300 100 Cl to Cl 100 100 30> 50 ClW1Cl 10> 50 10 0 VCS Cls 4 Cl 300 100 Cl 4 NH2 30 10 2 C1 NCS BrNCSCl 300 100 30 l 30 0 Br 2. Continuation of table 1 Active ingredient active ingredient kill degree (Constitution) concentration in in ppm after 24 hours N = C = S 300 100 Cl 4 Cl 30 <50 0 0 Br EXAMPLE 2 Sucking Mite Test / Psoroptes ovis on Sheep To produce the desired application concentration, 7 parts of the solvent mixture given in Example 1 are mixed with 3 parts of active ingredient and the mixture thus obtained is diluted with water.

Sheep that are heavily infected with Peoroptes ovis are infested, submerged. After 7 to 10 days, the effectiveness is determined, by checking the host animals for living parasites and the degree of killing expresses the parasite in k.

The results obtained can be seen from Table 2: Table 2 Active ingredient active ingredient kill degree (Constitution) concentration in in ppm after 7 days SCN CO2CH3 1000 100

Claims (3)

Claims: 1. Ectoparasiticidal agents, characterized by a content of aromatic isothiocyanates of the formula in which R stands for lower alkyl, alkoxy, 'alkyl mercapto, trihalomethyl, Halogen, nitro and / or cyano and n is 1 to 5, where R1 is an aliphatic or cycloaliphatic radical, R2 and R are hydrogen and / or lower aliphatic radicals. 2. Process for the preparation of ectoparasiticidal agents, thereby characterized in that aromatic isothiocyanates according to Claim 1 are mixed with extenders and / or mixes surfactants. 3. Use of aromatic isothiocyanates to combat Ectoparasites.