DE2061132C3 - Pesticidal compounds, processes for their production and preparations containing these compounds - Google Patents

Description

2,3-dimethylphenyl, 2,4-dimethylphenyl,

2,6-dimethylphenyl, 2,4,6-trimethylphenyl,

2,4,5-trimethylphenyl, 2,3,4-trimethylphenyl,

2-methyl-4-halophenyl,

2-halo-4-methylpheny],

2- halo-4,6-dimethylphenyl,

2,4-dihalo-6-methylpheny],

2-methyl-4-methoxyphenyl,

Phenyl or methyl phenyl

can mean, provided that

(A) if X and Y have the same meaning, the radicals are not phenyl, methyiphenyl or Are 2-methyl-4-halophenyl, and

(b) if X and Y are different, at least one of the radicals 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,4,6-trimethylphenyl, 2,3,4-trimethylphenyl, 2-methyl-4-halophenyl or 2-halo-4-methylphenyl is.

2. 1,5-di- (2,4-dimethylphenyl) -3-methyl _: 1,3,5-triazapenta-1,4-diene.

3. A method for producing a compound according to claim 1, characterized in that a formamidine of the general formula

XN = CH-NHCH ₃

with an iminomethylating agent of the general formula YZ ₁ in which Z has the meaning _NC, -N = CH-NHCH ₃ or -N = CHOR, where R is an alkyl radical having 1 to 4 carbon atoms and Y has the same meaning as in claim 1 , implements.

4. Pesticides, in particular acaricidal and insecticidal preparations, characterized in that they as active material a compound of the general formula of claim 1 together with a diluent or carrier.

The invention relates to the subject matter characterized in the claims.

The compounds according to the invention are new 1,5-diphenyl-3-methyl-1,3,5-triaza-penta-1,4-dienes with pesticides, especially acaricides and insecticides Properties. The compounds of the invention are suitable for the manufacture of pesticidal preparations which are used for Pest control, especially excellent for combating beef ticks and red spider mites are suitable.

The compounds of the present invention have the general formula I.

X-N = CH-N-CH = N-Y

CH ₃

wherein the radicals X and Y have the meanings listed in claim 1. Preferred connections are those in which the radicals X and Y are the same. That in the radicals X and Y, if appropriate, as a su substituent Halogen contained can be chlorine, bromine or fluorine.

The compounds according to the invention are by condensation of a formamide of the general Formula II

XN = CH-NHCH ₃

with a formamidine of the general formula III.

YN = CH-NHCH ₃

(III)

2 ^r >, where the radicals X and Y have the meaning given in claim 1. When X and Y are the same, it means the condensation of two molecules of the same formamidine.

The condensation can take place without any condensation

Ki medium by heating the formamidine or the mixture of formamidines at a suitable temperature, preferably in solution in a suitable inert organic solvents, for example xylene, toluene or chlorobenzene, are effected. One

v> suitable reaction temperature without condensing agent is generally in the range of 5C ° to 200 ⁰ C, in particular .from 70 ° to 180 ° C. A particularly suitable reaction temperature is 130 ° to 150 ° C and good results are in general characterized

■ in accomplished by a solution of formamidine or mixture of formamidines in xylene, for example the mixture available commercially holds the isomeric xylenes (boiling point 137 ° to 14O ⁰ C) reflux.

4) The condensation can also take place in the presence a suitable condensing agent, for example dimethylcarbumoyl chloride, dimethylthiocarbamoyl chloride, Ethyl trifluoroacetate or ethyl trichloroacetate are effected. These condensation agents affect

">» The temperature at which the condensation was carried out and in some cases, for example when X and Y are 2,4-dimethylphenyl, it is possible the condensation in the presence of the condensation agents described above at room temperature

τ. These condensation agents will be carried out suitably in about a molecular ratio based on the total molar amount of used Formamidine or formamidine mixture, used, although advantageously larger amounts of

with ethyl trifluoroacetate or ethyl trichloroacetate, especially at or near room temperature, are used can.

When Diincthylcai bamoyl chloride or dimethylthiocarbamoyl chloride used as a condensation agent

Iv-, if it is preferred, the reaction mixture is a suitable one Acid binding agent, for example triethylamine, to be added in order to absorb the hydrogen chloride formed. The formamidines of the general formula

my II and III are compounds of known type that by known methods, for example by reacting the appropriate arylamine hydrochloride with N-methylformamide in the presence of benzenesulfonyl chloride or p-toluenesulfonyl chloride can. Other known methods for the preparation of these formamidines consist in that one suitable ethyl formimidate reacts with methylamine

Depending on the process used to obtain and purify the formamidine, this Ό possibly still contain traces of free alkali. Since free alkali even in traces for the condensation is disadvantageous, this must be removed before the condensation in the absence of a condensing agent. This can be done by further purification or by neutralization with an acid such as tfenenzenesulfonic acid, p-toluene sulfonic acid or suljamic acid. An amount of acid from 0.01 to 0.05 equivalent per mole of formamidine is generally suitable.

Further compounds of general formula 1 -> o if one holds a compound of the general formula Ii

XN = CH-NHCH ₃ (II)

with a formimidate of the general formula IV

Y-N = CHOIR

(IV)

wherein the radicals X and Y have the meaning given above and the radical R is an alkyl radical with 1 to 4 carbon atoms, preferably an ethyl radical, implements.

The reaction can be carried out simply by heating a mixture of the formamidine and formimidate or a solution of the reactants in a suitable organic, inert solvent, such as, for example in acetonitrile, benzene, toluene, xylene or chlorobenzene. A suitable reaction temperature is in the range from 40 ° to 150 ° C, in particular 50 ° to 120 ° C. 4 »

The formimidates of the general formula IV are compounds of a known type which can be prepared by known processes, for example by reacting an arylamine of the general formula Y-NH ₂ with an alkyl orthoformate. 4>

For the preparation of the compounds according to the invention by reaction between formamidine and formimidate the reactants can also be formed in situ. For example, you can see the reaction between formamidine and formimidate also carry out as ■> »as follows:

(a) By heating methylamine with about two moles of the appropriate ethyl formimidate, for example by heating the reactants under autogenous pressure in a closed container. A suitable reaction temperature is in the range from 40 ° to 150 ° C, preferably from 50 ° to 120 ° C.

(b) By heating a mixture of an arylamine wi of the general formula YNH2, in which Y has the meaning defined above, a formamidine der general formula II, in which X has the meaning given above, and of ethyl orthoformate. Since it is known that the reaction between the "> Arylamine and ethyl orthoformate is catalyzed by acid, the reaction mixture should be a low Amount of a suitable acid, for example glacial acetic acid, can be added. The three reactants are suitably used in about equimolar proportions, although advantageous can be to use ethyl orthoformate in excess. A suitable reaction temperature is generally in the range from 40 ° to 150 ° C., preferably from 50 ° to 120 ° C. When carried out For the reaction, it is useful to add the arylamine YNH2 to the heated mixture of the other two Admit reactants.

Further compounds of the present invention are obtained by using a formamidine of the general Formula II

XN = CH-NHCH ₃ (II)

with an isocyanide of the general formula V

Y-NC (V)

in which the radicals X and Y have the meaning given above, - brings about reaction.

The reaction can be carried out by heating the reactants in the presence of a suitable catalyst, such as, for example, copper (I) oxide, copper (II) oxide or copper (I) chloride, a suitable reaction temperature generally in the range from 40 ° to 150 ° C, especially is from 50 ° to 12O ⁰ C. You can work in the presence of a suitable inert, organic solvent, for example benzene, toluene or acetonitrile, but the reaction is generally carried out without such a solvent.

The formamidine reactant of the general formula II can be prepared by the isocyanide of the general formula V with methylamine in the presence of a suitable catalyst, for example Copper (l) oxide or copper (l) chloride, converts. It may be useful to use this fermamidine without isolation with a further amount of isocyanide to form the desired compound of the general Shape! I implement.

A suitable amount of catalyst for the catalytic reactions with isocyanide described above is suitably in the range from 0.001 to 0.4 mol, preferably in the range from 0.01 to 0.2 mol, based on the isocyanide of the general formula V.

The isocyanides of the general formula V are by means of known processes, for example by reaction of the suitable formanilide with phosgene, accessible.

The asymmetric compounds of the present invention are obtained by using reactants in which X differs from Y If so, the reaction product becomes the general formula I generally a mixture of two symmetrical compounds and one asymmetrical Be connection. These three compounds can be represented by the following general formulas Vl to VIII are shown:

X '--- N = --- CH - N - CH = N-X'

CH.,

(Vl)

Y 'N-CII N CH- = N Y' (VIII

CH,

X'-N = CH-N-CH = N-Y '(VIII)

CH ₃

where X 'and Y' have the values given above for X and Y with the proviso that X 'and Y' are different.

When operating according to the methods of the present invention described above, it is preferred To use reactants in which the remainder ι ο ste X and Y are the same to the product of the general Obtain formula I in essentially pure form.

It has been found that the compounds of the general formula I defined above have valuable pest control properties to have. For example, the compounds have activity against acarids as indicated by their activity; the larvae of Cattle ticks, for example against the larvae of Boophilus microplus. Accordingly, they are Compounds for combating beef ticks, such as Boophilus microplus, can be used.

Preferred compounds of the present invention that have high activity against the larvae from Boophilus microplus are given in Table I below. In these connections are the radicals X and Y are the same and have the values given in the table.

Table 1

30th

link

X and Y

A.
B.
C.
D.
E.
F.
G

2,4-dimethylphenyl

2,3-dimethylphenyl

2-bromo-4-methylphenyl

2-fluoro-4-methylphenyl

2,4,6-trimethylphenyl

2,3,4-trimethylphenyl

2-chloro-4,6-dimethylphenyl

The compounds listed in Table I, and in particular compound A, also have Effectiveness against ready-to-lay females of Boophilus microplus, whereby the compounds cause oviposition have an inhibiting effect.

It has also been found that some of the compounds of the present invention have acaricidal activity against leaf-eating spider mites, especially against the red spider mite, such as Tetranychus spp. For example, the compound A in Table I and the compound has the general Formula I, in which X and Y are 2,4,5-trimethylphenyi residues (compound H), activity against eggs, larvae and fully developed animals, but especially against eggs and larvae, of Tetranychus urticae. Furthermore, the Compound A Efficacy against Tetranychus citri and Panonycus ulmi. The present invention provides therefore connections ζ \ :. i plant protection opposite leaf-eating spider mites available, for which one connects the plants or their surroundings with a compound of the general formula I, in which the radicals X and Y are identical and are 2,4-dimethylphenyl or 2,4,5-trimethylphenyl are treated. A suitable use ratio of these compounds is in general Range from 0.056 to 112 kg / ha and usually im Range from 0.125 to 11.25 kg / ha.

The compound A in Table 1 and the compound H were also found to have insecticidal activity exhibit. For example, these compounds have activity against Coccideae, for example "California Coccidea". Compound A also has activity against aphids, for example Megoura viciae and Aphis fabae.

The compounds of general formula I can be referred to chemically as triazapentadienes. According to this designation, Compound A is in Table I l, 5-di- (2,4-dimethylphenyl) -3-methyl-3,5-triazapenta -l _T-l, 4-diene.

The present invention further provides pest control preparations, especially against acarids, these being a compound of the general formula I defined above, together with an extender or diluent or carrier. The diluent or carrier can be a solid or a liquid, optionally together with a surface-active agent, for example a dispersing, emulsifying or wetting agent is used.

The preparations of the invention can also be in the form of concentrates which are prior to use must be diluted with an appropriate amount of water or another diluent. Typical preparations of the invention include, for example, dust powder, dispersible powder, Solutions, emulsifiable concentrates, dispersions, emulsions, fumes and aerosols.

A dust powder contains the active ingredient in an intimate mixture with a solid powdery extender, for example with kaolin.

A dispersible powder contains the active ingredient in finely divided form together with one or more Dispersants, and provides a stable aqueous dispersion after mixing the powder with water. The dispersible powder is usually also a finely divided, inert, solid extender, such as Kaolin or kieselguhr added.

The active ingredient is in the form of fine particles in the dust powders and the dispersible powders. Preferably, the majority of the particles, i.e. at least 95%, should be smaller than 50 µ, where approximately 75% of the particles should have a size of 5 to 20 μ.

An emulsifiable concentrate, also known as a "miscible liquid," contains a solution of the Active ingredient in a water-immiscible solvent, together with one or more emulsifying agents. When the emulsifiable concentrate is mixed with water, an emulsion is obtained.

To combat beef ticks, the preparations of the invention can be applied to the soil, for example on the floor of stables. However, it is preferred to treat the cattle externally with the Treat preparations. The selected diluent or extender must of course be used here or the carrier selected may be one which is substantially non-toxic and non-irritating to the cattle.

Preferred preparations for the external treatment of cattle are so-called "cattle immersion baths". These are to be understood as preparations that contain an active ingredient together with a diluent or carrier, the nature of the diluent or carrier and its proportion being such that after dilution with a suitable amount of water

stable aqueous preparations are formed which are used for treating cattle according to the conventional Dipping and spraying methods are suitable. The beef dips of the present invention can for example in the form of dispersible powders or emulsifiable concentrates.

The above-described preparations of the present invention can be prepared by processes known to those skilled in the art of pest control compound approach.

Concentration of the compound of the general form ·! I in the above-described concentrates of the present invention can / v eitgehend vary and, for example in the range of 5 to 95% Gew./ wt. Of the composition, depending on the physical lie ι ί properties of the constituents.

The concentration of the compound of general formula I in the preparations used to combat of the pests mentioned here are provided, is generally in the range of 0.001 to 10% wt / Wt., More usually from 0.005 to 5% w / w. lie.

The preparations of the present invention can be used as active ingredients more than one compound of the general Formula I and optionally also one or more additional pesticides, for example contain one or more fungicides, additional insecticides or additional acaricides. Such an additional pesticide can, for example, an organophosphorus compound, a jo Carbamate. a diphenyl bridge compound or a chlorinated hydrocarbon such as benzene hexachloride, be.

The following examples serve to explain the invention in more detail. y,

B e i s ρ i e I 1

A solution of 19.4 g of N-2,4-dimethylphenyl-N'-methylformamidine and 0.3 g of p-toluenesulphonic acid in 195 ml of dry xylene was left in the absence of moisture for 48 hours to form methylamine held at reflux. The xylene was distilled off under reduced pressure and the solid residue recrystallized twice from isopropyl alcohol. 1,5-Di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene was obtained; Melting point 88 ° to 89 ° C. A satisfactory elemental analysis was obtained.

The formamidine used above was obtained as follows. A mixture of 55.1 g of 2,4-dimethylaniline hydrochloride, 83.7 g of p-toluenesulfonyl chloride and 150 ml of N-methylformamide was stirred, the temperature being reduced to 20 ° to 35 ° C. by occasional cooling was held. After the exothermic reaction had ended, the mixture was at for 4 hours Stirred at room temperature, poured into ice / water and made alkaline with 10N sodium hydroxide solution, whereby the temperature of the mixture was kept below 10 ° C. The precipitated solid was filtered off with Washed water free of alkali, dried at room temperature and recrystallized from cyclohexane. One received N-2,4-dimethylpheny] -N'-methylformamidine; Melting point 75 ° to 76 ° C.

Example 2

In a manner similar to Example 1 and using the reflux times given below became the following 1.S-Di-Z-penta-1,4-dienes manufactured.

Table II Z Reflux Enamel link duration Point (H) CQ 2,3-dimethylphenyl 72 124-126 A. 2,6-dimethylphenyl 72 138-140 B. 2,4,6-trimethylpheny] 96 96-97 C. 2,4,5-trimethylphenyl 96 103-104 D. 2,3,4-trimethylpheny] 48 133-134 E. 2-bromo-4-methylphenyl 96 126-127 F. 2- fluoro-4 methylphenyl 144 Ϊ42-Ί43 G 2-chloro-4-methylphenyl 60 137-139 I. 2-chloro-4,6-dimethylphenyl 72 122-124 J 2-bromo-4,6-dimethylphenyl 72 130-131 K 2,4-dichloro-6-methylphenyl 72 165-166 L. 2-methyl-4-methoxyphenyl 72 71-73 M.

Satisfactory elemental analyzes were obtained for all of these compounds.

Example 3

1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene. Melting point 88 ° to 89 ° C., was prepared as described in Example 1, but with no p-toluenesulfonic acid was added to the reaction mixture. The elemental analysis was satisfactory.

Example 4

A solution of 20 g of N-2,4-dimethylphenyl-N'-methylformamidine in a mixture of 22.8 g of ethyl trifluoroacetate and 2OmI dry benzene was under Stirring for 8 hours with exclusion of moisture at 50 ° to 60 ° C. The mixture was under reduced pressure to remove benzene, excess ethyl trifluoroacetate and that in the reaction ethanol and N-methyltrifluoroacetamide by-products formed narrowed, the latter being

Compound sublimed from the reaction mixture during the distillation. The remaining oil was diluted with 14 ml of isopropyl alcohol and the resulting solution was cooled. The crystalline product was recrystallized from isopropyl alcohol to give 1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene; Melting point 88 ° to 89 ° C. A satisfactory elemental analysis was obtained.

Example 5

A solution of 3.8 ml of dimethylcarbamoyl chloride in 10 ml of dry ether was stirred into a solution of 6.5 g of N-2,4-dimethylphenyl-N'-methylformamidine and 5.5 ml of triethylamine in 80 ml of dry ether at 0 ° C added dropwise. The temperature of the mixture was allowed to rise to room temperature with stirring and was kept at that temperature overnight. It was then filtered and the filtrate was concentrated under reduced pressure at room temperature. An oil and solid slurry was obtained which gradually solidified. The solid product was washed with 2N hydrochloric acid, then with saturated aqueous sodium bicarbonate solution and finally with water. The solid was dried and recrystallized from isopropyl alcohol. 1,5-Di- (2,4-dimethylphenyl) -3-methyl-1,3,5-tnazapenta-1,4-diene was obtained; Melting point 88 ° to 89 ⁰ C. This gave a satisfactory elemental analysis.

Example 6

A solution of 10 g of N-2,4-dimethylphenyl-N'-methylformamidine in 11 g of ethyl N-2,4-dimethylphenyl formimidate was heated under anhydrous conditions on a steam bath with stirring for 25 hours, wherein the ethanol formed during the reaction distilled off. The last traces of ethanol were evaporated under reduced pressure and the hot reaction mixture diluted with 7 ml of methanol. the resulting solution was cooled to give a crystalline product. After recrystallization from isopropyl alcohol one obtained 1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene; Melting point 88 ° bis 89 ° C. A satisfactory elemental analysis was obtained.

The formimidate starting material used in the above procedure was prepared as follows. A mixture of 500 ml Äihyiüi'ihüiurniiai, 242 g 2,4-dimethylaniline, 0.1 g of 2,4-dimethylaniline hydrochloride and 1000 ml of acetonitrile was poured into a distillation device introduced and heated on the steam bath for 5 hours, with ethanol and acetonitrile distilling off. Excess ethyl orthoformate was removed under reduced pressure and the residue distilled in a high vacuum. Ethyl N-2,4-dimethylphenylformimidate was obtained; Boiling point 65 "C / 03 mm.

Example 7

2,4-Dimethylaniline (55 g) became one on the steam bath with stirring over 5 hours heated mixture of 73.8 g of N-2,4-dimethylphenyl-N'-methylformamidine, 85 ml of ethyl orthoformate and 1.5 ml of glacial acetic acid were added dropwise, and that during the reaction formed ethanol distilled off. The reaction mixture was continued with stirring on the steam bath Heated for 40 hours, excess ethyl orthoformate and residual traces of ethanol under reduced Pressure was removed and the reaction mixture cooled to form a solid product. To Recrystallization from isopropyl alcohol gave 1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene; Melting point 88 ° to 89 ° C. A satisfactory elemental analysis was obtained.

Example 8

Liquid methylamine (1.55 g) cooled to -30 ° C was added to 17.7 g of ethyl N-2,4-dimethylphenylformimidate at the same temperature in a Pyrex glass tube. The tube was sealed and on the

Heated 2n steam bath for 70 hours. Ethanol was removed from the reaction mixture under reduced pressure and the hot residue is diluted with 5 ml of methanol. The resulting solution was cooled and man obtained crystals of 1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene; Melting point 88 ° to 89 ° C. Recrystallization from propan-2-ol provided a analytical sample of this compound for which a satisfactory elemental analysis has been obtained.

Example 9

A solution of 8.2 g of N-2,4-dimethylphenyl-N'-methylformamidine in 10 g of ethyl-N-4-chloro-2-methylphe-

J ^r > nyl formimidate was heated with stirring on a steam bath for 20 hours, during which the ethanol formed during the reaction distilled off. Residual traces of ethanol were removed under reduced pressure and the hot reaction mixture with 7 ml of methanol

4 »diluted. The resulting solution was cooled, and a crystalline product with a melting point of 120 ° to 125 ° C. was obtained. Gas-liquid chromatography analysis and mass spectroscopy showed that this product is a mixture of 1,5-di- (2,4-dimethyl-

4 ^r > phenyl) -3-methyl-1,3,5-triazapenta-1,4-diene, 1,5-di- (4-chloro-2-methylphenyl) -3-methyl-1,3,5- triazapenta-1 A- diene and 1- (4-chloro-2-methylphenyl) -5- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene. The first two compounds were made from the mixture

μ by means of fractional distillation from methanol in pure Shape isolated.

Example 10

In a manner similar to that in Example 9, using equimolar proportions of the corresponding formamidine XN = CH-NHCH3 and formimidate YN = CH-OC ₂ H _5, the resulting reaction

bo mix under reduced pressure for removal concentrated by residual traces of ethanol. The residues obtained were analyzed by gas-liquid chromatography analyzed and consisted of mixtures of an asymmetric triazapentadiene and two symmetrical triazapentadienes of the general formulas VI, VII and VIII described above, where the amounts of which are given in Table III below.

at 11th 2061 132 % W / og. B. 12th VIl Vl I 14 VIII 23.8 14.2 Table III Subsidiaries 45 16.3 25.7 Residue X 'position on the phenyl ring in 46 16.1 25.4 2,4- (CHj) ₂ Y 'position 42.6 29.2 20.2 1 4-C1-2-CHj none 47.2 e i s d i e J 2,4- (CH ₃ ) ₂ none K 2,4- (CH ₃ I ₂ 2-CHj L. game 11 2,3- (CH ₃ ),

A mixture of 3.24 g of N-2,4-dimethylphenyl-N'-methylformamidine, 2.62 g of 2,4-dimethylphenyl isocyanide and 0.08 g of cuprous oxide was stirred for 5 hours under anhydrous conditions on the Steam bath heated. The hot reaction mixture was diluted with 5 ml of isopropyl alcohol and removed for removal of the copper (l) oxide filtered. The filtrate was cooled to give a crystalline product obtained from isopropyl alcohol Provided 1,5-di- (2,4-dimethylphenyl) -3-methyll,3,5-iriazapenta-1,4-diene; Melting point 88 ° up to 89 ° C. A satisfactory elemental analysis was obtained.

The 2,4-dimethylphenyl isocyanide used in the above process was prepared in the manner that 2,4-dimethylformanilide according to Angew. Chem., 1965, 77 (11), 492-504, reacted with phosgene.

Example 12

Liquid methylamine (1.2 g) of -30 ⁰ C was added to a mixture of 10 g of 2,4-dimethylphenyl isocyanide and 0.4 g of copper (I) oxide of the same temperature in a Pyrex glass tube. The tube was sealed and brought to room temperature. After the exothermic reaction had ended, the tube was heated on the steam bath for 15 hours. The hot reaction mixture was diluted with 10 ml of isopropyl alcohol and the resulting solution was cooled to crystallize. After recrystallization of the product from isopropyl alcohol, 1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene was obtained; Melting point 88 ° to 89 ° C. A satisfactory elemental analysis was obtained.

Example 13

A dispersible powder was obtained by grinding a mixture of the following ingredients.

1,5-di- (2,4-dimethylphenyI) -

1,4-diene

Sodium-N-methyi-N-palmitoyl-

taurat

Sodium dioctyl sulfosuccinate

Kieselguhr

% Wt. 25.0

6.0

0.5
68.5

Other similar dispersible powders were prepared using the triazapentadiene in the above Formulation by the compound B, C, D, E, F, G or J of Example 1 was replaced.

(a) An emulsifiable concentrate was made from the foils ingredients:

% W / v 25.0

2.5
2.5
100.0

*) A nonylphenyl ethylene oxide condensate was used with an average content of 14 moles of ethylene oxide per mole of nonylphenol.

1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-diene
Calcium dodecylbenzenesulfonate
Nonylphenoxypolyethoxyethanol *)
Xylene, anhydrous, ad

(b) An emulsifiable concentrate was prepared using the xylene of the above formulation was replaced by anhydrous isophorone.

Other emulsifiable concentrates have been made that contain the triazapentadiene in the above Formulations (a) and (b) by the compound B, C, D or E of Example 1 was replaced.

Example 15

w A dust powder was prepared by grinding the following ingredients in a hammer mill.

1,5-di- (2,4-dimethylphenyl) - % Wt. 4 "> 3-methyl-1,3,5-triazapenta 3.0 1,4-diene Kieselguhr talc 20.0 77.0

Determination of the effectiveness against larvae of the cattle tick Boophilus microplus

Larvae of the cattle tick Boophilus microplus were sprayed with an aqueous solution or dispersion of the compound to be examined and dried. The percentage of mortality was determined after 48 hours. Duplicate tests were carried out on the various concentrations of the compound under test in order to obtain approximate LD ₅₀ values. The compounds according to the invention, which are described in more detail in Table IV below, were investigated. Chlordimeform [N '- (4-chloro-2-methylphenyl) -N, N-dimethy] formamidine] was also investigated as a comparative compound. This compound is an acaricide on the market under the name "Galecron".

Table IV Y-ring Activity against Substiluemcn im about larvae 2,4- (CH ₃ ), LD50 X ring 2,3- (CH ₃ ) ₂ (ppm w / v) 2,6- (CH ₃ J ₂ 3 2,4- (CHj) ₂ 2,4,6- (CH ₃ ) 3 40 2,3- (C H 3) 2 2.3 / - (CH ₃ ) ₃ 140 2,6- (CH ₃ ) ₂ 2-Br-4-CH ₃ 85 2,4,6- (CHj) ₃ 2-F-4-CH3 30th 2,3,4- (CH ₃ J ₃ 2-Cl-4,6- (CH ₃ ) ₂ 85 2-Br-4-CH ₃ 2,4-CI ₂ -6-CH ₃ 40 2-F-4-CH3 2-CH ₃ -4-CH ₃ O 72 2-Cl-4,6- (CH ₃ ) ₂ none 180 2,4-CI ₂ -O-CH ₃ none 230 2-CH ₃ -4-CH ₃ O 2,4- (CH ₃ ) ₂ 4th 2,4- (CH ₃ ) ₂ 2,4- (CH ₃ I ₂ 18th 2-CH ₃ -4-Cl 2,4- (CH ₃ ) ₂ 23 2-CH ₃ -4-Cl 9 2-Br-4-CHj 23 2,4,5- (CHj) ₃ 230 Chlordimeform

The triazapentadiene of Example 1 and compounds A, B, C, E, F, G, J, L and M of Example 2 had lower LD50 values than 250 ppm w / v (specified as concentration of the test binding in the aqueous spray preparation).

Determination of effectiveness against ovarian larvae
from Tetranychus urticae

Freshly laid eggs of Tetranychus urticae on slices of French bean leaves with a diameter of 2 cm were sprayed with an aqueous dispersion of the compound to be tested. After 10 days the living larvae were counted on the Biatt disc and the percentage of mortality was determined. the Experiments were repeated three times at different concentrations of the test compound to approximate LD50 values expressed as ppm w / v test compound in the aqueous spray. The triazapentadiene of Example 1 and the compound D of Example 2 gave LD50 values that are less than Were 20 ppm.

Claims (1)

Patent claims:
1. Compounds of the general formula XN = CH-N-CH = NY
CH ₃ wherein the radicals X and Y are identical or different and