NZ197704A - Synergistic ectoparasiticidal/insecticidal combination of 2-(2,4-dimethylphenyl)imino-3-methylthiazoline and a pyrethroid - Google Patents

Description

New Zealand Paient Spedficaiion for Paient Number 1 97704 1 977 0 Priori,y ^omplete Specifjcation Fl|e[|. l3-7_8.' Class: I.

Publication Date: Rl JOCTj'985"""" p 0. Journal, N0: § > Patents Form No.

NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION "PESTICIDAL COMPOSITION" 13 JUL 1981 i "i/WE CIBA-GEIGY AG of Klybeckstrasse 141, 4002 Basle, Switzerland, a Swiss Corporation, hereby declare the invention, for which I/we pray that a patent may be granted to res/us, and the method by which it is to be performed, to be particularly described in and by the following statement:— (followed by page I A.) - lA- I 97 7 Case 5-12958/1+2/= PESTICIDAL COMPOSITION The present invention relates to a novel pesticidal composition containing as active ingredient an active-substance combination, and to its use for combating ectoparasites, especially mites, including in particular ticks and mange mites, and for combating insects, particularly sucking lice and biting lice, flies and fly larvae, as well as mosquitoes and mosquito larvae.

The active substance combinations on which the compositions according to the invention are based have a synergistic activity which exceeds, in an advantageous manner, the additive effect of the combined individual active substances. The active-substance combinations according to the invention comprise the following individual active substances: 2- (2 1 , 4'-dimethylphenylimino)-3-methyl-thiazoline (compound A) and at least one pyrethroid of the general formula I R - C - 0 - (CH) - R, 11 l n 2 m 0 R wherein R is Cy-C-Q-aralkylene consisting of a C^-C^-alkylene group, preferably methylene, and a C^-Cg-aromatic ring, preferably phenyl, the C^-C^-aralkylene being 197704 unsubstituted or being substituted in the alkylene moiety by a C^-Cg-alkyl, preferably isopropyl, or in the arcxnatic moiety by a C^-C^-alkyl or by 1 to 3 halogen atans, preferably chlorine, or R is C^-Cg-cycloalkyl, preferably cyclopropyl, which is unsubstituted or substituted by: - one to four C^-C^-alkyl grcups, preferably methyl, - one to four halogen atcms, preferably chlorine, - one to three C^-C^-alkenyl groups, preferably isobutenyl, - cne to three C^-Cg-haloalkyl groups, preferably having 2 to 4 C atcms and 1 to 6 halogen atoms, preferably 1 to 4 chlorine and/or brcmine atcms, - one to three C2-C6haloalkenyl groups, preferably having 2 to 4 C atans and 1 to 6 halogen atcms, preferably 1 to 4 chlorine and/or brcmine atcms, or - one or two C^-C^-alkylene or C^-Cg-alkenylene groups each bound by way of a spiro atom, and each preferably having 3 or 4 C atcms and being unsubstituted or substituted by an annularly-linked C^-Cg-alkylene or C^-Cg- alkenylene group; is hydrogen, cyano or C2"-C2-aIkynyl; is a C^-C^-open-chain olefin unsubstituted or substituted by phenyl, or is a group of the formula CH v A3 • • i i ✓ o in which is 2-propenyl, 2-butenyl, 2-pentenyl or 2, 4-pentad i enyl, or E^"is a group of the formula ^ .* \- \ / • mm wherein Y is oxygen, sulfur or methylene, and Z is fluorine, chlorine, brcmine, or methyl, and m is zero, 1 or 2, or a group of the formula 1 97704 wherein the aromatic ring can be 2- or 4-fold hydrogenated, or a group of the formula 21 \ /•-ch2-6h=ch- • »• or a group of the formula —K- —H—R V 3 wherein is hydrogen, phenylalkylene having 7 or 8 C atoms, preferably benzyl, or it is C^-C^-alkynyl, preferably propynyl-(2), and X is oxygen or -NH; and n is zero or 1; including the geometrical, diastereomeric and enantiomeric isomers embraced by the general formula I, and also mixtures of isomers of one or more compounds of the formula I .

A preferred substituted aralkyl group among those denoted by R is the group of the formula I _ B * ^ I \ ✓- ? * — B in which Q is halogen, preferably a chlorine atom in the 4-position, and B is an alkyl group having 1 to 6 C atoms, preferably a branched-chain alkyl group, particularly isopropyl.

Particularly preferred of the substituents of the cycloalkyl groups denoted by R are, as haloalkyl, the 2,2-dichloro-l,2-dibromoethyl group, and, as haloalkenyl, the monochlorovinyl and dichlorovinyl groups, as well as the monobromovinyl and dibromovinyl groups. 197704 A preferred substituted cycloalkyl group among those denoted by R is that of the formula R S / V \ / \ r/ Xl c d wherein Ra is hydrogen, C^-Cg-alkyl, preferably methyl, or halogen, particularly chlorine; R^ is C^-C^-alkyl, preferably methyl, halogen,especially chlorine, or R^ is C2~C^-alkenyl, preferably iso-butenyl, C2~C^-haloalkyl having 1 to 4 halogen atoms, preferably chlorine and/or bromine atoms, particularly 2,2-dichloro-l,2-dibromoethyl or C2~C^-haloalkenyl having 1 to 4 halogen atoms, preferably chlorine and/ 0 or bromine atoms, especially monochlorovinyl, dichlorovinyl, monobromovinyl or dibromovinyl; or Ra and R^ together are C2~C^-alkylene, preferably propylene; R and R^ independently of one another are each: hydrogen, C^-C^-alkyl, preferably methyl, C2~C^-alkenyl, preferably isobutenyl, or C2-Cg-haloalkenyl having 1 to 3 halogen atoms, preferably chlorine or bromine atoms, especially monochlorovinyl, dichlorovinyl, ';'v monobromovinyl or dibromovinyl; or "^R and R^ together are: cyclic C2-C^-alkylene or C^-C^- alkenylene each bound by way of a spiro atom, and "each 197704 unsubstituted or substituted by an annularis-linked C^-C^-alkenylene group, preferably a group of the formula \A.

I II » Pyrethroids for forming the active-substance combinations contained in the compositions according to the invention are for example: o BrCljC-CHBr-CH^ca-C-O-Ca— ^ (B) CH3 01 (isomeric mixture, known from the N.Z. Patent Specification No. 186448; 0 " ^ ^ Cl23rC-CHBr-C^CH-C-0-<S—^ ^ ^ <6*3 ra V< >-F (isomeric mixture, known from the N.Z. Patent Specification No. 186449 CH(CH_), C1-- —CE - c - 0 - CH-* N. /t\\ M I \=/ ... <D> 0 CN \ / (isomeric mixture, known from the British Patent Specification No. 1,439,615, common name "Fenvalerate"); 107704- 0 11 y"~V Br.C-CH-CH^-^CH-C-OCH-*^ y -(£) r L, • • CH 3 3 \ / (known from Nature (London), 1974, 248, 710; trade name DECIS) or 0 « /"% (F) C12C-CB-CH—CH-C-OCH-'^ N- A ' K ' i 3 °"< > • a* .(known from Pestic. Sci., 1975, j6, 537, common name "Cypermethrin").

The compounds described in the foregoing as active-substance components of the compositions according to the invention are already known as compounds which individually exhibit pesticidal activity.

The active-substance component (2-(2',4'-dimethyl-phenylimino)-3-methylthiazoline is described in the N.Z. Patent Specification No. 180791.

The combination of different chemical compounds to produce a synergistic intensification of activity for combating insect pests is gaining to an increasing extent in importance because of the possibility thus offered for effectively counteracting the ever more frequent appearance of resistance of parasites to individual compounds. Consequently, the growing need to increase the amounts of active substance used on account of the occurrence of such resistance phenomena can be largely avoided. The resulting saving in the amount of active substance applied has both economical and, by virtue of a lessening of environmental tamination, significant ecological advantages.

Mixtures of various classes of substances, for example 1 977 o pyrethrins, pyrethroids, carbamates and phosphoric esters, have already been described as synergistically effective preparations in the pesticidal field. It has however been shown that these combination preparations do not in every respect fulfil the requirements they are expected to meet in practice, particularly with regard to improved effectiveness, toxicity and economy in use.

It has now been found that the active-substance combinations which are contained in the compositions according to the invention, and which consist of 2-(2',4'-dimethylphenylimino)-3-methyl-thiazoline and pyrethroids, display a high ectoparasticidal, especially acaricidal, activity, and insecticidal activity. This is aimed in particular against ectoparasites, such as mites, including especially ticks and mange mites, and against insects, such as sucking lice and biting lice, flies and fly larvae, as well as mosquitoes and mosquito larvae. The significance of the present invention lies above all in the fact that the novel paraciticidal compositions can be successfully used against pests harmful to hygiene, and that it hence makes an important contribution, by virtue of the prevention of the spread of disease, towards the maintenance of health of humans and animals. In agriculture, moreover, the yield from productive animals is considerably improved by application of the compositions according to the invention.

The range of 1:100 to 100:1 applies with regard to the determining weight ratios of the thiazoline compound to the pyrethroid compounds in the active-substance combinations according to the invention. The combination ratio of thiazoline compound to pyrethroid compound in the range of 1:50 to 50:1 is especially suitable for inducing the synergistic effect, and within these limits the ranges of 1:20 to 20:1 and 1:10 to 10:1 are particularly effective.

The invention on which the compositions according to <1 I 97 7 0 the invention are based is further illustrated by the following Examples. The analysis of the biocidal activity of substance mixtures on specific species is performed according to the method of Y.-P. Sun and E.R. Johnson [J. Econ. Entomol. 53, 887 (I960)].

The mutual action of the combined active substances was examined by determining the actual toxicity indices of the components and of the mixture of the components on the basis of the dose-effect curve. The theoretical toxicity of the mixture corresponds to the sum of the toxicity indices, calculated from the percentage of each component multiplied by the respective toxicity index. The total toxicity or co-toxicity coefficient of a mixture is therefore actual toxicity index of the mixture x -^00 theoretical toxicity index of"the mixture A coefficient of a mixture of almost 100 indicates an essentially similar effect of the two pesticides; an independent effect usually gives a coefficient of less than 100, whereas a coefficient significantly above 100 denotes the occurrence of synergism.

The effectiveness of mixtures consisting in each case of the compound A and one of the aforementioned compounds B to E was tested on ticks (Boophilus microplus). The . ticks used were of an OP-resistant strain. To determine the EC^q values (effective concentration for 507o of the test insects), a series of dilutions, both of the formulated individual compounds and of the mixtures), were prepared.

Example 1: Dip application against ticks Forty ticks (Boophilus microplus) were fixed in dorsal position on an adhesive tape in a Petri dish of 9 cm diameter, and were treated with a dilution of the active substance and active-substance combination, 1 977 0 respectively, in standard WHO water. The dilution solution was for this purpose poured into the dish, so that the test insects were covered by the solution. The temperature of the solution in the dish was held at 20 to 25°C, and the duration of immersion was 1 hour. The active-substance solution was subsequently poured off, and the dish was rinsed. The dish containing the test insects was dried overnight in the laboratory; the insects were subsequently incubated at 28°C with about 90% relative humidity and were left for 3 to 4 weeks under these conditions. The effectiveness of the substances used was evaluated on the basis of the reduction of the number of emerged larvae.

The ECjjq values were determined in ug/ml from the results obtained, and the co-toxicity coefficients calculated (when this index is clearly above 100, the mutual effect of the two mixture components is more than additive, that is to say, synergism occurs). The results shown in Table 1 are mean values from several individual tests each involving 40 test insects per active-substance concentration.

Table 1 Compound or mixture of compounds A B A:B A:B A:B A C A:C A:C A:C A:C Weight ratioi of the mixture 1:1 4:1 1:4 1:1 1:4 8:1 4:1 EC50 test 16 6.8 4.1 4.4 5.6 16.4 2.6 2.3 1.8 3.7 2.4 "EC50 theoretical 9.5 11.9 7.9 4.4 3.2 9.8 6.9 Co-toxicity index 231 270 142 195 182 262 290 0 1 •-4 o o o Compound or mixture of compounds Weight ratio of the mixture EC50 test EC50 theoretical Co-toxicity index A • 16-4 - D 12.2 - A:D 1 1 2.9 13. 9 466 A:D 4 :1 4.29 9. 6 223 A < - E 3.8 - A:E 1 :10 1.7 4 230 A:B 1 6.4 13. 7 214 A:E ! 1 11.7 16. 2 138 Table 1 (continuation) 1 977 0 The effectiveness of the combinations formed from the compounds A and F was tested on flies.

Example 2: Application against fly larvae The active substances and active-substance combinations, respectivelyj were dissolved in each case in a standard medium, and from the solutions obtained were prepared dilution series (dilution factor 0.7). The diluted solutions were then transferred, in aliquot parts of 50 ml, to glass flasks, and into each flask were placed 25 freshly emerged fly maggots of the Lucilia sericata species. The specimens were subsequently kept in an incubator at 33°C with about 10% relative humidity for 72 hours. On completion of the test, the results were evaluated by counting the living fly larvae present. Each test was repeated twice.

The LCj.q values in ppm were determined from the results obtained, and the co-toxicity coefficients calculated (when this index is clearly above 100, the mutual effect of the two mixture components is more than additive, that is to say, synergism has occurred). The results summarised in Table 2 are mean values from several individual tests.

Table 2 Compound or mixture of compounds Weight ratio of the mixture LC50 • test LC50 theoretical Co-toxicity index a - 308.85 - - F - 9.45 - - a:F 1:1 8.53 18.34 215 a:F :1 21.71 74.6 344 A:F 100:1 68.30 232,6 340 1*7704 14 The active-substance combinations on which the compositions according to the invention are based are used according to the invention together with suitable carrier and/or additives. Suitable carriers and additives are solid or liquid and correspond to the substances common in formulation practice, such as natural or regenerated substances, solvents, dispersing agents, wetting agents, adhesives, thickeners and/or binders. For application, the active substance combinations are processed according to the invention into the form of dusts, emulsion concentrates, granulates, dispersions, sprays, solutions or suspensions. Furthermore, aqueous preparations or concentrates of the active-substance combinations are used according to the invention for cattle dips and spray races, and are also applied by the pour-on, handspray and hand-dressing methods.

The compositions according to the invention are produced by intimate mixing and/or grinding of the active-substance combinations with suitable carriers, optionally with the addition of dispersing agents or solvents which are inert to the active substances. The active-substance combinations can be obtained and used in the following forms: solid preparations: dusts, scattering agents and granulates liquid preparations: a) water-dispersible concentrates of active-substance combinations:- wettable powders, pastes and emulsions; b) solutions.

The content of an active-substance combination in the preparations described above is between 1 and 80% by weight ? 977 04 Example 3 Emulsion concentrate parts by weight of an active-substance combination are dissolved in 70 parts by weight of xylene, and to this solution are added parts by weight of an emulsifier consisting of a mixture of an arylphenyl polyglycol ether and the calcium salt of dodecylbenzenesulfonic acid.

Water can be added in any proportion to the emulsion concentrate to form a milky emulsion.

Example 4 Emulsion concentrate to a maximum of 50 parts of an active-substance combination are dissolved at room temperature, with stirring, in 30 parts by weight of dibutyl phthalate, parts by weight of solvent 200 (low-viscous, highly aromatic petroleum distillate), to 35 parts by weight of Dutrex 238 FC (viscous highly aromatic petroleum distillate), and to this solution are added 10 parts by weight of an emulsifier mixture consisting of castor oil polyglycol ether and the calcium salt of dodecylbenzenesulfonic acid.

Milky emulsions are formed by adding water to the emulsion concentrate obtained. 1 97 7 Example 5 Wettable powder to 50 parts by weight of an active-substance combination are vigorously mixed, in a mixing apparatus, with parts by weight of an absorbent carrier (silicic acid K 320 or Wessalon S), 55 to 80 parts by weight of a carrier (bolus alba or kaolin B 24), and a dispersing agent mixture consisting of parts by weight of a sodium lauryl sulfonate, and parts by weight of an alkyl-aryl-polyglycol ether.

This mixture is ground in a dowelled disc mill or air-jet mill to a particle size of 5-15 ^im. The wettable powder thus obtained give a good suspension in water.

Example 6 Dust parts by weight of a finely ground active-substance combination are thoroughly mixed with 2 parts by weight of a precipitated silicic acid, and 92 parts by weight of talcum.

J97704

Claims (41)

WHAT WE CLAIM IS:

1. An ectoparasiticidal and insecticidal composition which contains an active-substance combination in synergistic proportions comprising 2-(2', 41 -dimethylphenylimijno) -3-irethy 1-thiazoline (compound A) and at least one pyrethroid of the general formula 0 B. wherein R is C-^-C^-aralkylene consisting of a C^-C^-aIJcylene group, and a Cg-Cg-arcmatic ring, the C^-C^.j-aralkylene being unsubstituted or being substituted in the alkylene moiety by a Cj-Cg-alkyl or in the aromatic moiety by a C^-C^-alkyl or by 1 to 3 halogen atcms or R is C^-Cg-cycloalkyl, which is unsubstituted or substituted by: - one to four C^-Cg-alkyl groins, - one to four halogen atcms, - one to three C2~Cg-alkenyl groups, - one to three C2~Cg-haloalkyl groups having 1 to 6 halogen atans, - one to three C2-Cg-haloaUcenyl groups having 1 to 6 halogen atoms, or - one or two C2~Cg-aIkylene or C2~Cg-alkenylene groups each bound by way of a spiro atom, and being unsubstituted or substituted by an annularly linked C^-Cg-alkylene or C^-Cg-alkenylene group; R^ is hydrogen, cyano or C2-C2-alkynyl; R2 is a C^-C^-open-chain olefin unsubstituted or substituted by phenyl, or is a group of the formula CH I 3 R4\ I I 0 in which is 2-propeny1, 2-butenyl, 2-pentenyl or 2,4-pentadienyl, or R2 is a group of the formula 197704 - 18 - V\-v JK ^ \ / II wherein Y is oxygen, sulfur or methylene, and Z is fluorine, chlorine, bromine or methyl, and m is zero, 1 or 2, or a group of the formula •*v \ « M .1 *WS / 2 II 0 wherein the aromatic ring can be 2- or 4-fold hydrogenated, or a group of the formula 91 ^ ^ T* ch2-ch-ch- • mm fvZ I STENT OFFICE m7 SEP 1984 or a group of the formula -A- —tt—R, V 3 wherein is hydrogen, phenylalkylene having 7 or 8 C atoms or it is C^-C^-alkynyl; and X is oxygen or -NH; and is zero or 1; including the geometrical, diastereomeric and enantiomeric isomers embraced by the general formula I, and also mixtures of isomers of one or more compounds of the formula I, together with at least one inert carrier and additive.

2. A composition according to Claim 1, wherein R in the general formula I is a phenylalkylene group which is unsubstituted or is substituted in the alkylene moiety 137704 - 19 - by an alkyl having 1 to 6 carbon atoms, or in the phenyl moiety by an alkyl having 1 to 4 carbon atoms or by 1 to 3 halogen atoms, and R^, and n have the meanings given under the formula I in claim 1.

3. A composition according to Claim 1, wherein R in the general formula I is a phenylalkylene group substituted in the phenyl moiety by 1 halogen atom, and having in the alkylene moiety 1 to 5 carbon atoms, and R^, Rj and n have the meanings given under the formula I in Claim 1.

4. A composition according to Claim 1/ wherein R in the general formula I is a phenylalkylene group substituted in the alkylene moiety by an isopropyl, and R^, R^ and n have the meanings given under the formula I in Claim 1.

5. A composition according to Claim. 1» wherein R in the general formula I is a phenylalkylene group substituted in the phenyl moiety by a chlorine atom, and *1' R2 an<* n kave the meanings given under the formula I in Claim 1.

6. A composition according to Claim 1, wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by 1 to 4 methyl groups or by 1 to 4 halogen atoms, and R^, R2 and n have the meanings given under the formula I in Claim 1.

7. A composition according to Claim.1' wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by 2 N.2. PATENT OFFire -4 OCT 1984 _RECElVFn 197704- - 20 - chlorine atoms, and R^, and n have the meanings given under the formula I in Claim 1.

8. A composition according to Claim 1, wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by an alkenyl group having 2 to 5 carbon atoms, and R^, ^ an<* n have the meanings given under the formula I in Claim 1.

9. A composition according to Claim 1/ wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by an iso-butenyl, and R^, R2 and n have the meanings given under the formula I in Claim 1.

10. A composition according to Claim 1, wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by a haloalkyl having 2 to 4 carbon atoms and 1 to 4 chlorine and/or bromine atoms, and R^, R2 and n have the meanings given under the formula I in Claim 1.

11. A composition according to Claim 1, wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by a haloalkenyl having 2 to 4 carbon atoms and 1 to 4 chlorine and/or bromine atoms, and R^, R2 and n have the meanings given under the formula I in Claim 1.

12. A composition according to Claim 1, wherein R in the general formula I is a group of the formula N.Z. PATENT OFFICE -7 SEP 1984 P.f-CFHIVSD wherein Q is halogen, and B is an alkyl group having 1 to 4 carbon atoms, and R^, R2 and n have the meanings given under the formula I in Claim 1. V\4_ 1 \ _ / ••• - 21 - 187704

13. A composition according to Claim 12, wherein R is the group of the formula

14. A composition according to Claim 1, wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by a 2,2-dichloro-l,2-dibromoethyl, and R^, R^ and n have the meanings given under the formula I in Claim 1.

15. A composition according to Claim 1, wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by a monochlorovinyl or a monobromovinyl, and R^, R2 and n have the meanings given under the formula I in Claim 1.

16. A composition according to Claim 1/ wherein R in the general formula I is a cycloalkyl group which has 3 to 6 carbon atoms and which is substituted by a dichlorovinyl or a dibromovinyl, and R^, R2 and n have the meanings given under the formula I in Claim 1.

17. A composition according to Claim 1, wherein R in the general formula I is a group of the formula r . wherein Rfl is hydrogen, C^-Cg-alkyl or halogen, R^ is C^-Cg-alkyl, halogen, C2-C^-alkenyl, haloalkyl having 1 to 4 halogen atoms, or ^"Cg-haloalkenyl having 1 to 4 halogen atoms, or N-Z. PATEN V - 22 - 197704 Ra and together are C2*C^-alkylene, Rc and R^ independently of one another are each: hydrogen, C^-C^-alkyl, C2"C^-alkenyl or C2~C^-haloalkenyl having 1 to 3 halogen atoms, or g) . Rc and R^ together are: cyclic C2-C^-alkylene or C^"C6~ alkenylene, each bound by way of a spiro atom, and each being unsubstituted or substituted by an ^ annularly-linked C4~C6-alkenylene group.

18. A composition according to Claim 17, wherein the substituent Rfl is methyl or chlorine, and R^, Rfi and R^ have the meanings given in Claim 17. w

19. A composition according to Claim 17, wherein the substituent R^ is methyl, isobutenyl, chlorine, haloalkyl having 2 to 6 carbon atoms and 1 to 4 chlorine and/or bromine atoms, or it is haloalkenyl having 2 to 6 carbon atoms and 1 to 4 chlorine and/or bromine atoms, and R . R ' a* c and R^ have the meanings given in Claim 17.

20. A composition according to Claim 17, wherein the substituent R^ is the 2,2-dichloro-l,2-dibromomethyl group or the monochlorovinyl or dichlorovinyl group or the monobromovinyl or dibromovinyl group, and R , R and R, a C O have the meanings given in Claim 17.

21. A composition according to Claim 17, wherein the substituents R& and R^ together are propylene.

22. A composition according to Claim 17, wherein the substituents Rc and R^ independently of one another are each methyl, isobutenyl, a haloalkenyl group having 2 to carbon atoms and 1 to 3 chlorine and/or bromine atoms, and Ra and R^ have the meanings given in Claim 17.

23. A composition according to Claim 17,.-wherein the substituents Rfi and R^ independently of one another - 23 - 197704 are each the monochlorovinyl, monobromovinyl, dichlorovinyl or dibromovinyl group, and Rfi and R^ have the meanings given in Claim 17.

24. A composition according to Claim 17, wherein the substituents R£ and R^ together are the group of the formula and Rfi and R^ have the meanings given in Claim 17.

25. A composition according to Claim 1, wherein R^ in the radical R2 is the benzyl group or the propynyl-(2) group, and X has the meaning given under R2, and R, R^ and n have the meanings given under the formula I in Claim 1.

26. A composition according to Claim 1, wherein R2 in the general formula I is a group of the formula in which R^ is 2-propenyl, 2-butenyl, 2-pentenyl or 2,4-pentadienyl, and R, R^ and n have the meanings given in Claim 1.

27. An ectoparasiticidal and insecticidal composition according to Claim 1, which contains an active-substance combination consisting of the compounds A and AX I II II • . . II II CE . ' 3 ft • • •' 0 v<™> 197704 - 24 -

28. An ectoparasiticidal and insecticidal composition according to Claim 1, which contains an active-substance combination consisting of the compounds A and 0 It Cl2BrC-CHBr-C^-JH-C-0-CH—* cfljtchj cn /*~f

29. An ectoparasitisidal and insecticidal composition according to Claim 1, which contains an active-substance combination consisting of the compounds A and CH(CH-)_ Cl-» —CE - c - 0 - CH— • \ „ 7 \ / mm* II | ' tat \ s % 0 cn o—^

30. An ectoparasiticidal and insecticidal composition according to Claim 1, which contains an active-substance combination consisting of the compounds A and 0 " Br.C-CH-CH - CH-C-OCH—^ y Q I • dLj CH3 CN /• M.7. PATENT OFFiCE -7 SEP 1984 f'cCEIViHD

31. An ectoparasiticidal and insecticidal composition according to Claim 1» which contains an active-substance combination consisting of the compounds A and 197704 - 25 - ci2c-ch- 0 II -och— V V*wr \ / XL. CN - - 3 ^3 V< ,

32. An ectoparasiticidal and insecticidal composition according to Claim 1# wherein the weight ratio of the thiazoline compound to the pyrethroid compound^ in the active-substance combination is 1:100 to 100:1.

33. An ectoparasiticidal and insecticidal composition according to Claim 1, wherein the weight ratio of the thiazoline compound to the pyrethroid compounds) is 1:50 to 50:1.

34. An ectoparasiticidal and insecticidal composition according to Claim L wherfein the.weight ratio of the thiazoline compound to the pyrethroid compound^) is 1:20 to 20:1.

35. An ectoparasiticidal and insecticidal composition according to"Claim 1> wherein the weight ratio of the thiazoline compound to the pyrethroid compound^) is 1:10 to 10:1.

36. A method of combating ectoparasites at a non-human locus, which method comprises applying to the locus an effective amount of an active-substance combination according to Claim 1.

37. A method of combating-mites at a locus, which method comprises applying to the locus an effective amount of an active-substance combination according to Claim 1. -V; ; ' /, a „ - 26 - 197704

38. A method of combating ticks at a non-human locus, which method comprises applying to the locus an effective 1 amount of an active-substance combination according to Claim 1.

39 A method of combating sacking lice and biting lice at a non-human locus, which method comprises applying to the locus an effective amount of an active-substance combination according to Claim 1.

40. A method of combating flies and fly larvae at a locus, which method comprises applying to the locus an effective amount of an active-substance combination according to Claim 1.

41. A method of combating mosquitoes and mosquito larvae at a non-human locus, wMch method comprises applying to the locus an effective amount of an active-substance combination according to Claim 1. BALDWIWr^P^ /f /Y ™" a^orneysfor'The' applicants