NZ199659A

NZ199659A - Substituted 2-(anilinomethyl)-2-imidazolines

Info

Publication number: NZ199659A
Application number: NZ199659A
Authority: NZ
Inventors: M Boger; U Burckhardt; H Kristinsson; G Mattern; W Traber
Original assignee: Ciba Geigy Ag
Priority date: 1981-02-09
Filing date: 1982-02-08
Publication date: 1985-08-16
Also published as: IL64959A0; AR230058A1; BR8200675A; AU8026582A; EP0058635B1; AU554954B2; DE3264474D1; EP0058635A1; GB2092582B; GB2092582A; ZW2582A1; IL64959A

Description

New Zealand Paient Spedficaiion for Paient Number 1 99659 •8/ Priority ^ '^-2-sa icomptow CIKSK AU< 1985 pubttoation Date: ... • • • • * ^ P 6. jouhm'> no? • • • • m*in$ 1 9965 Patents Form No.5 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION "Substituted 2-(anilinomethyl)-2-imidazoline derivatives, processes for producing them, compositions containing these derivatives, and the use thereof for combating pests -I-,WE CIBA GEIGY AG, a Swiss Corporation, of Klybeckstrasse 141, 4002 Basle, Switzerland, hereby declare the invention, for which 5/we pray that a patent may be granted to me/us,,and the method by which it is to be performed, to be particularly described in and by the following statement ffollowed hv rape ! A ^ - 1A- 199659 Case 5-13281/82 Substituted 2-(anilinomethyl)-2-imidazoline derivatives, processes for producing them, compositions containing these derivatives, and the use thereof for combating pests The present invention relates to novel substituted 2-(anilinomethyl)-2-imidazoline derivatives, to processes for producing them, to pesticidal compositions containing the said derivatives as active ingredients, and to methods for combating pests by application of the novel compounds. 2-(Anilinoalkyl)-2-imidazoline derivatives exhibiting pesticidal, particularly ectoparasiticidal, activity are known. (cp<—for example Britioh Patent Specification No. 2,023,603i European Fatont Specification Mo. 03001)6^7 and— German Offcnlegungsschriften Nos .—2,756^630 and 2,756,639). There are provided with the present invention novel compounds of this type which have a pronounced action against pests, especially against members of the order Acarina, and which are particularly suitable for practical application by virtue of their advantageous biological properties.

The novel substituted 2-(anilinomethyl)-2-imidazoline derivatives according to the invention correspond to the formula I Ri\ 2 /N— y \ 4 y-nh-ch2—' (I). 199659 .wherein and independently of one another are each a chlorine atom or the methyl group, ^OR _Y is the group -P or -CH=N-Rt-, IIs p X 4 wherein R^ is methyl or ethyl, R^ is alkyl having 1 to 4 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 to 4 carbon atoms, or phenyl, X is an oxygen atom or a sulfur atom, and R^ is an unsubstituted or substituted pyridinyl group which is linked by way of one of its carbon atoms to the main part of the molecule, and which has substituents selected from the group comprising halogen and alkyl having 1 to 4 carbon atoms; and the present invention includes also the acid addition salts of these compounds.

Structurally, the compounds of the formula I embrace /0R3 phosphorus-containing derivatives (Y = -P and TR4 pyridinylimine derivatives (Y = -CH=N-R^).

The alkyl and alkylthio groups denoted by R^ are: the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl or tert-butyl group, as well as the methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio or tert-butylthio group.

By alkyl groups as substituents of the pyridinyl group R^ are meant the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl groups; and by halogen are meant fluorine, chlorine, bromine and iodine, preferably chlorine or bromine. 1 9965 The compounds of the formula I are in the form of free bases or in the form of acid addition salts, for example mineral salts, and can be used according to the invention in both forms.

It has now been shown that the compounds of the formula I according to the invention surprisingly have a pronounced action against plant-damaging members of the order Acarina (for example mites of the families'. Tarsonemidae, Erophyidae, Tyroglyphidae, Glycyphagidae and particularly Tetranychidae) ,and also against ectoparasitic members of this order (for example mites and ticks of the families: Sarcoptidae, Dermanyssidae, Ixodidae and Argasidae), which can seriously harm productive animals, and against members of the orders Phthiraptera (animal lice) and Phytophthires (plant lice), as well as against Diptera, which belong to the Calliphoridae family. To be mentioned as member of the Calliphoridae family is in particular the genus Lucilia, including especially the species Lucilia sericata (blowfly).

The compounds according to the invention are able, when applied to plants, to penetrate through the surface of the leaf into the inside of the leaves. The compounds of the formula I, with the inclusion of their acid-addition salts nontoxic to warm-blooded animals, are particularly suitable therefore for combating sucking plant pests, especially phytoparasitic members of the order Acarina, in crops of productive plants and ornamental plants, especially in fruit and vegetable crops, and in particular in the case of citrus cultivation.

To be emphasised in the zooparasitic field is especially the combating of ectoparasitic mites on productive animals, with particular reference being made in this respect to ticks as a subgroup of mites.

The effectiveness against pests is coupled with a 199659 4 low level of toxicity to warm-blooded animals, which is favourable for practical application, so that the compounds of the formula I and their acid addition salts nontoxic to warm-blooded animals are particularly suitable for combating pests of the order Acarina in crops of productive plants and ornamental plants, as well as for combating ectoparasitic ticks and mites on productive animals.

Preferred among the compounds of the formula I, in the phosphoric ester series, are those compounds, including the acid addition salts thereof, in which X is oxygen, is ethyl, is alkylthio having 3 or 4 carbon atoms, and and R2 have the meanings defined under the formula I. Of the formamidines of the formula I, however, preferred compounds, including the acid addition salts thereof, are those wherein R^ is an unsubstituted or methyl-substituted pyridinyl group linked in the 2-position to the main part of the molecule, and R^ and R2 have the meanings defined under the formula I.

The following compounds, including their acid addition salts, are to be considered as being particularly preferred by virtue of their effectiveness: l-(0-ethyl-S-sec-butyl-thiophosphony3)-2-(2' ,31 -dimethyl-anilinomethyl)-2-imidazoline, 1- (0-ethyl-S-isobutyl-thiophosphonyl)-2- (2 1,3' -dimethyl-anilinomethyl)-2-imidazoline, 1- (0-ethyl-S-n-propyl-thiophosphonyl)-2- (21 ,31 -dimethyl-anilinomethyl)-2-imidazoline, 1-(0-ethyl-ethyl-thiophosphinyl)-2-(2 1 ,31-dimethylanilino-methyl)-2-imidazoline, 1- (0-ethyl-S-isobutylthiophosphonyl)-2- (21,3 1 -dichloro-anilinomethyl)-2-imidazoline, 199659 1- (0-ethyl-S-n-propylthiophosphonyl)-2- (2 ' ,3 1 -dichloro-anilinomethyl)-2-imidazoline, 1- (O-ethyl-S-n-propyl-thiophosphonyl)-2-(2' -methyl-3 1 -chloroanilinomethy1)-2-imidazoline, 1- (0-ethyl-S-sec-butyl-thiophosphonyl)-2- (2 1 -methyl-3 ' -chloroanilinomethyl)-2-imidazoline, N-([2-(2, 3-dimethylanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(6-methylpyridin-2-yl)-imine, N-([2-(2,3-dimethylanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(pyridin-2-yl)-imine, N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(pyridin-2-yl)-imine, N-([2-(2,3^dichloroanilinomethy1)-2-imidazolin-l-yl]-methylidene)-N-(3-methylpyridin-2-yl)-imine, N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(6-methylpyridin-2-yl)-imine, and N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(4-methylpyridin-2-yl)-imine.

The compounds of the formula I are produced, using known processes, by for example reacting a compound of the formula II !rix A / N— (II) a) with a compound of the formula Ilia X (Ilia) R^, R.2, R3, and X in the formulae II and Ilia having the 199659 meanings defined under the formula I, and "Hal" being a halogen atom, especially a chlorine or bromine atom, at a temperature of between -20° and 80°C under normal or slightly elevated pressure, in the presence of a base and preferably in a solvent or diluent inert to the reactants; and b) with a compound of the formula 111b R6 - 0 - CH = N - R5 (111b) R^, R2 and R,- in the formulae II and Illb having the meanings defined under the formula I, and R^ being methyl or ethyl, at a temperature of between -20° and 120°C, undeir normal or slightly elevated pressure, and preferably in a solvent or diluent inert to the reactants.

Suitable solutions or diluents for use in the reactions described in the foregoing are for example: ethers and ethereal compounds, such as diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran; aromatic hydrocarbons, such as benzene, toluene and xylenes; and ketones, such as acetone, methyl ethyl ketone and cyclohexanone.

Suitable bases are in particular: tertiary amines, such as trialkylamines, pyridines and dialkylanilines, also hydroxides, oxides, carbonates and bicarbonates of alkali metals and alkaline-earth metals, as well as alkali metal alcoholates, for example potassium tert-butylate and sodium methylate.

The compounds of the formula I produced in this manner can be converted into their acid salts by methods known per se.

The starting materials used in the aforementioned reactions are known (cp. German OffcnlcgungDQchriftcn Nog. •2,750,902 and 2,756,638), or can be produced by methods analogous to known methods. 199659 Example 1: Production of 1-(O-ethyl-S-n-propyl-thio-phosphonyl)-2-(21,31-dimethylanilinomethyl)-2-imidazoline To a suspension of 8.1 g of 2-(21,3'-dimethylanilinomethyl) -2-imidazoline in 100 ml of toluene at 0° to 10°C are added 4.3 g of triethylamine, and subsequently is added dropwise at 0° to 16°C, with continuous stirring, a solution of 8.1 g of O-ethyl-S-n-propyl^thiochlorophosphate in 50 ml of toluene. The reaction mixture obtained is stirred for one hour at about 10°C; 100 ml of water are then added, and the toluene phase is repeatedly washed with a small amount of water. After evaporation of the previously dried toluene solution and drying at 50°C under high vacuum, there is obtained the compound of the formula .n— / \ —nh-ch0-*: 3 7n in the form of clear yellow oil having a refractive index of nj^ = 1.5601. 19 96 8 Example 2: N-([2-(2,3-Dimethylanilinomethyl)-2-imidazolin-l-yl ]-methylidene)-N-(3-methylpyridin-2-yl)-imine 8.0 g of 2-(2,3-dimethylanilinomethyl)-2-imidazoline and 6.6 g of N-(3-methylpyridin-2-yl)-formiminoethyl ether of the formula IV are stirred with 100 ml of toluene for 5 hours at a temperature of 70°C. The reaction mixture obtained is concentrated by evaporation, and the residue is . recrystallised twice from toluene,to thus obtain N-([2-(2,3-dimethylanilinomethyl)-2-imidazolin-1-yl-methylidene)-N-(3-methylpyridin-2-yl)-amine of the formula V ■ ch -ch„-0-ch=n-\ \ 3 1 \i ^ (IV) (V) in the form of beige-coloured powder; m.p.

The following compounds of the formula in an analogous manner: 176-178°C. I are produced 1 996 Table la <.= >-nh-ch2-(n_ ; X=k0R3 \ *4 No. r1 r2 R3 R4 X Physical data. la CH3 CH3 c2h5 s-ch-ch -CH Jh3 0 n^0 1,5510 2a CH3 CH3 c2h5 ' /H3 s-ch -clf ch3 0 n^° 1,5516 3a ch3 CH3 c2h5 s-ch2-ch2-ch3 s m.p. 59-61°c 4a ch3 CH3 c2h5 s-ch2-ch2-ch3 0 n^° 1,5601 5a ch3 ch3 c2h5 c2h5 s highly viscous 6a ch3 ch3 c2h5 °-c2h5 0 n^° 1,5332 7a ch3 ch3 c2h5 c6h5 s n^° 1,6073 8a CH3 ch3 ch3 o-ch3 0 n^° 1,5440 9a ci ci c2h5 s-ch2-ch^ 3 ch3 0 n^° 1,5656 10a ci ci c2h5 s-ch-ch2-ch3 ch3 0 n^° 1,5639 11a ci ci c2h5 s-ch2-ch2-ch3 0 n^° 1,5743 12a ci ci c2h5 s-ch2-ch2"ch3 s 1,6010 13a ci ci c2h5 °-c2h5 0 n^° 1,5505 14a ci ci CH3 °'CH3 0 m.p. 92-94°C a ci ci c2h5 c6h5 s 1,6230 16a ci ch3 c2h5 s-ch2-ch2-ch3 0 oil 20 nD 1'5674 .oil nj0 1,5.615 17a ci CH3 c2h5 s-ch-ch -ch Ah, 0 19965 Table lb V /2 f> \ = >-™-ch 2-v ch=n~r Z No.

R1 R2 R5 m.p. °C lb CH3 CH3 /CH3 "V/ 173-175 2 b ch3 CH3 /=\ — • • w \H3 193-195 3 b CH3 CH3 /=\ — • • w 194-196 — • • w 4 b ch3 CH3 181-183 b ch3 ch3 /=\ -y/ c»3 176-178 6 b CI: Cl /=N\ "V/ 172-174 7 b Cl Cl — • • w 193-195(D) 8 b Cl Cl "W 175-177 9 b Cl Cl /CH3 — • • W | 181-183 1 99659 No.

R 1 R2 R3 m.p. ° C b cl cl /=\ % / 202-204 11 b cl CH3 \h3 — • o c&3 181-182 12b cl ch3 — • • w 181-183 The compounds of the formula I are used as such according to the invention, or they form a constituent of compositions containing in addition suitable carriers or additives, or mixtures of such substances. Suitable carriers and additives can be solid or liquid and they correspond to the substances common in formulation practice, for example natural or regenerated substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders and/or fertilisers.

The acaricidal action of the compositions according to the invention can be broadened by the addition of other acaricides and/or insecticides. Suitable additives are for example: organic phosphorus compounds; nitrophenols; formamidines; ureas; pyrethrin-like compounds; carbamates and chlorinated hydrocarbons.

Representatives of the classes of substances referred to as additives to the compositions according to the invention are for example the following compounds: 0-(2-chloro-l-(2,4-dichlorophenyl)-vinyl)-0,0-diethyl-phosphate, 0,0-diethyl-0-(2-isopropyl-6-methyl-pyrimidin-4-yl)-phosphothionate, 199659 cis-0,0-dimethyl-0-(2-dimethylcarbamoyl-1-methylvinyl)-phosphate, N'-(4-chloro-o-toluene)-N,N-dimethylformamidine, N-methyl-bis-(2,4-xylyliminomethyl)-amine, N-(2-methyl-4-chlorophenyl)-N1,N1-dimethylthiourea, 2-(21,4'-dimethylphenylimino)-3-methyl-thiazoline, 3-methyl-5-isopropylphenyl-N-methyl-N-n-butanoyl-carbamate, 2-isopropoxyphenyl-N-methy1carbamate, (+)-3-(2,2-dichlorovinyl)-2,2-dimethy1-cyclopropane-carboxylic acid-(a-cyano-3-phenoxybenzyl) ester, (S)-a-cyano-3-phenoxybenzyl(1R)-cis-3-(2,2-dibromovinyl-2,2-dimethylcyclopropanecarboxylic acid ester, (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethyl-cyclopropane-carboxylic acid-(S)-(a-cyano-3-phenoxybenzyl) ester, as well as the compound of the formula: C1 0 Cl--f ^"-(IH-CH - - (! - 0 - CH - 'f x* x—x jn ! " : c<\H3 V \ The compositions according to the invention can be for example in the form of dusts, granulates, dispersions, solutions and suspensions, and also in the form of water-dispersible wettable powders, pastes, emulsions and emulsion concentrates.

The content of active substance (compound of the formula I) in the compositions described above is between 0.1 and 95%; it is to be mentioned in this respect that, with application by means of suitable devices, also higher concentrations can be used. 1996 5 9 The active substances of the formula I can be formulated for example as follows: Emulsion concentrate I parts by weight of the active ingredient are dissolved in 70 parts by weight of xylene, and to the solution are added 10 parts by weight of an emulsifying agent consisting of a mixture of an arylphenolpolyglycol ether and the calcium salt of dodecylbenzenesulfonic acid.

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

Emulsion concentrate II to a maximum of 30 parts by weight of the active ingredient are dissolved at room temperature, with stirring, in 30 parts by weight of dibutylphthalate, 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 the solution are added parts by weight of an emulsifier mixture consisting of castor-oil polyglycol ether and the calcium salt of dodecylbenzenesulfonic acid.

The emulsion concentrate thus obtained produces milky emulsions in water.

Wettable powder to 30 parts by weight of the active ingredient are thoroughly mixed, in a mixing apparatus, with 5 parts by weight of an absorbing carrier material (finely dispersed silicic acid) and 55 to 80 parts by weight of a carrier material (bolus alba or kaolin) and a dispersing agent mixture consisting of 1 9965 14 parts by weight of a sodium lauryl sulfonate and 5 parts by weight of an alkyl-aryl-polyglycol ether.

This mixture is ground to 5-15 ^um in a dowelled disc mill or air-jet mill. The wettable powder thus obtained gives a good suspension in water.

Dust parts by weight of the finely ground active ingredient 2 parts by weight of a precipitated silicic acid and 93 parts by weight of talc.

"Pour-on" solution 100.8 g = 100 ml.

The active substance is dissolved in the benzyl alcohol with stirring and if necessary with gentle heating. The sodium dioctylsulfosuccinate and the peanut oil are added to the solution and dissolved with heating and thorough stirring.

Example 3: Action against piant-damaging acarides: Tetranychus urticae (OP-sensitive) and Tetranychus cinnabarinus (OP-tolerant) The primary leaves of Phaseolus vulgaris plants are infested, 16 hours before the test for acaricidal action, with an infested piece of leaf from a mass culture of Tetranychus urticae (OP-sensitive) and Tetranychus cinnabarinus (OP-tolerant), respectively (tolerance is with respect to compatibility with Diazinon). The infested plants treated in this manner are sprayed dripping wet with are thoroughly mixed with active ingredient sodium dioctylsulfosuccinate benzyl alcohol peanut oil .0 g 3.0 g 48 .0 g 19.8 s

Claims

1 9965 9 - 15 - test solutions containing 400 and 200 ppm, respectively, of the compound to be tested. An assessment is made after 24 hours and again after 7 days, by examination of the imagines and larvae (all mobile stages) under a binocular microscope, of the living and dead individuals. One plant is used per concentration and per test series. The plants are standing during the test in greenhouse compartments at 25°C. The compounds of the formula I effect in this test at least a 90% mortality rate against individuals of the species Tetranychus urticae and Tetranychus cinnabarinus. Example 4: Action against ectoparasitic acarides (ticks) Rhipicephalus bursa (imagines and larvae), Amblyomma hebraeum (<j> imagines, nymphs and larvae) and Boophilus microplus (imagines, larvae - OP-sensitive and OP-tolerant) The test objects used are larvae (in each case about 50), nymphs (in each case about 25) and imagines (in each case about 10) of the tick species Rhipicephalus burse, Amblyomma hebraeum and Boophilus microplus. The test insects are immersed for a short time in an aqueous emulsion or solution containing the compound to be tested at a suitable concentration of between 0.1 and 1000 ppm. The emulsions or solutions in the test tubes are then absorbed with cotton wool, and the wetted test insects are left in the test tubes treated in this manner. An evaluation of the mortality rate achieved at each concentration is made after 3 days for larvae and after 14 days for nymphs and imagines. The compounds of the formula I effect in this test at least a 90%> mortality rate against larvae, nymphs and imagines of the species Rhipicephalus bursa and Amblyomma hebraeum, and also against imagines and larvae (OP-resistant and OP-sensitive) of the species Boophilus microplus. The compounds Nos. la, 2a, 4a, 5a, 9a, 11a, 16a, 17a, lb, 3b and 7b - 10b are 100% effective. t 996 - 16 - WHAT +/WE CLAIM 15:- ■WIIAT IS CLAIMED tS~:

1. A compound of the formula I Rl\ /^2 s'~\ /— (I) -x ,-nh-ch wherein and R2 independently of one another are each a chlorine atom or the methyl group, ^DR3 ■ Y is the group -Pv or -CH=N-R,-, x r4 wherein R^ is methyl or ethyl , R^ is alkyl having 1 to 4 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 to 4 carbon atoms, or phenyl, X is an oxygen atom or a sulfur atom, and R^ is an unsubstituted or substituted pyridinyl group which is linked by way of one of its carbon atoms to the main part of the molecule, and which has substituents selected from the group comprising halogen and alkyl having 1 to 4 carbon atoms, including acid addition salts thereof.

2. A compound of the formula I according to Claim 1, wherein R^ and R2 independently of one another are each chlorine or methyl, and, in the group Y, R^ is ethyl, R^ is alkylthio having 3 or 4 carbon atoms, and X is an oxygen atom, or R^ is an unsubstituted or methyl-substituted pyridinyl group linked in the 2-position to the main part of the molecule, 199659 - 17 - including acid addition salts thereof.

3. Any one compound from the group comprising: 1- (0-ethyl-S-sec-butyl-thiophosphony])-2- (2',3 ' -dimethyl-anilinomethyl)-2-imidazoline, 1- (0-ethyl-S-isobutyl-thiophosphony])-2- (2 1,3 1 -dimethyl-anilinomethyl)-2-imidazoline, 1- (0-ethyl-S-n-propyl-thiophosphony])-2- (21,3 1 -dimethyl-anilinomethyl)-2-imidazoline, 1- (0-ethyl-ethyl-thiophosphinyl)-2- (2', 31 -dimethylanilino-methyl)-2-imidazoline, 1- (0-ethyl-S-isobutylthiophosphonyl)-2- (21,3 ' -dichloro-anilinomethyl)-2-imidazoline, 1- (0-ethyl-S-n-propylthiophosphonyj)-2- (21,3 1 -dichloro-anilinomethyl)-2-imidazoline, 1- (0-ethyl-S-n-propyl-thiophosphonyI)-2- (2' -methyl-3 1 -chloroanilinomethyl)-2-imidazoline, 1- (0-ethyl-S-sec-butyl-thiophosphonyl)-2- (2 1 -methyl-3 1 -chloroanilinomethyl)-2-imidazoline, N-(12-(2,3-dimethylanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(6-methylpyridin-2-yl)-imine, N-([2-(2,3-dimethylanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(pyridin-2-yl)-imine, N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(pyridin-2-yl)-imine, N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(3-methylpyridin-2-yl)-imine, N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene) -N-(6-methylpyridin-2-yl)-imine, and 1 996 - 18 - N-([2-(2,3-dichloroanilinomethyl)-2-imidazolin-l-yl]-methylidene)-N-(4-methylpyridin-2-yl)-imine.

4. A process for producing a compound of the formula I Ri\ /R2 /" (i) i \./^v! ; ^ wherein R^ and R2 independently of one another are each a chlorine atom or the methyl group, ^0R3 Y is the group -P or the group -CH=N-R,-, wherein it^-n -> X 4 R^ is methyl or ethyl, R^ is alkyl having 1 to 4 carbon atoms, alkoxy having .1 or 2 carbon atoms, alkylthio having 1 to 4 carbon atoms, or phenyl, X is an oxygen atom or a sulfur atom, and R^ is an unsubstituted or substituted pyridinyl group which is linked by way of one of its carbon atoms to the main part of the molecule, and which has substituents selected from the group comprising halogen and alkyl having 1 to 4 carbon atoms, which process comprises reacting a compound of the formula II Eix A /•"\ ' ' /- (II), wherein R-^ and R2 have the meanings defined under the formula I, either a) with a compound of the formula Ilia - 19 - 199659 Hal - ^°R3 Y (Ilia) wherein R^# R^ and X have the meanings defined under the formula I, and "Hal" is a halogen atom*at a temperature of;- ao°c ijo> 9;between -200 and 800Q€, in the presence of a base selected from the group consisting of tertiary amines, pyridines and dialkylanilines, also hydroxides, oxides, carbonates and bicarbonates of alkali metals and alkaline-earth metals,;as well as alkali metal alcoholates; or b) with a compound of the formula Illb;R6 - 0 - CH = N - R5 (Illb);wherein R5 has the meanings defined under the formula I,;and Rc is methyl or ethyl,at a temperature range of -xo between -200 and 1200nC.;

5. A pesticidal composition which contains as active ingredient, together with carriers and/or additives, a compound of the formula I;Ri\ ^2 m;< ;-NH-CV 1;wherein and R2 independently of one another are each a chlorine atom or the methyl group,;^0R3;Y is the group -P or -CH=N-Rr, wherein;X 4 is methyl or ethyl,;R^ is alkyl having 1 to 4 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 to 4 carbon atoms, or phenyl,;X is an oxygen atom or a sulfur atom, and R^ is an unsubstituted or substituted pyridinyl group which is linked by way of one of its carbon atoms to the main part of the molecule, and which has;•Sib;1 99 6;- 20 -;substituents selected from the group comprising halogen and alkyl having 1 to 4 carbon atoms,;or an acid addition salt thereof.;

6. A process for combating pests by application of a compound of the formula I;Vn2 (i);^ v y wherein and R2 independently of one another are each a chlorine atom or the methyl group,;^0R3;Y is the group -P or -CH=N-Rr, wherein if^u X 4;is methyl or ethyl,;R^ is alkyl having 1 to 4 carbon atoms, alkoxy having;1 or 2 carbon atoms, alkylthio having 1 to 4 carbon atoms, or phenyl,;X is an oxygen atom or a sulfur atom, and;R^ is an unsubstituted or substituted pyridinyl group which is linked by way of one of its carbon atoms to the main part of the molecule, and which has substituents selected from the group comprising halogen and alkyl having 1 to 4 carbon atoms,;or an acid addition salt thereof.;

7. A process according to Claim 6, whereby the pests are representatives of the order Acarina.;

8. A process according to Claim 6, whereby the pests are ectoparasites.;199659;- 21 -;

9. A process according to Claim 6, whereby the pests are members of the order Phthiraptera or Phytophthires.;

10. A process according to Claim 6, whereby the pests are members of the family Calliphoridae.;v;J9Fl*l9S5$