IL33455A - 2,4-dinitro-6-alkylphenyl-ethers and acaricidal preparations containing them - Google Patents

Description

and acaricldal preparations containing them The invention relates to aearicidal preparat ons containing them and to a method of combating pests of the order The present invention provides the use of compounds of the general formula I for combating members of the order wherein R represents a cyclohexyl or cyclopentyl represents a hydrogen an alkyl or alkenyl residue having at most 4 carbon atoms which is optionally or an alkynyl residue having at most 4 carbon atoms or a phenyl residue which is optionally substituted by one or more halogen atoms or a nitro and represents a hydrogen atom or a methyl These active substances may be manufactured by reaction of a compound of formula II with a second compound of formula III R wherein Rg and the given and each represents a or a nitro and wherein one of the Y and Z represents a halogen especially chlorine or and the other an OH group which can also in the form of an alkali alcoholate or alkaline earth optionally in the presence of an agent which binds hydrogen and with subsequent of the resulting other in the case where represent a hydrogen The compounds of the invention are outstandingly suitable for combating pests of the order Acarina mites and spinning including also those showing resistance towards phosphoric acid The compounds also have a chemosterilising As an especially active there should be mentioned those compounds of formula I in which represents a butyl or butyl represents a hydrogen atom or a chlorovinyl or ethynyl group and represents a hydrogen atom or a methyl The invention also provides new compounds of formula and their indicated use in which formula R represents a cyclohexyl or cyclopentyl represents a alkyl or alkenyl residue or unsubstituted alkenyl residue having at most 4 carbon atoms or a phenyl residue which is optionally substituted by halogen or and represents a hydrogen atom or a methyl The invention further relates to compositions which contain these new compounds of formula together with a for one or more of the following dispersing wetting adhesives or In the substances can be in a liquid or solid in dry or in the form of wettable powders or dusting or through gas phase These methods are described in detail in Patent or British Patent or Swiss Patent In many cases the use of granules for the uniform release of active substances over a prolonged period of time is of These granules can be manufactured by dissolving the active substance in an organic absorption or adsorption of this solution by a mineral or polymer adsorbent material and removal of the They can also be manufactured by mixing the active substances of formula I with polymeri3able which a merisation is carried which leaves the active substances with the granulation carried out whilst the is still In order to dusting agents and ing such for for combating mites in it is possible to use calcium but also cork wood flour and other materials of vegetable origin as solid The various forms in which the active substances of the present invention can be used can be provided in the usual manner with addition of substances which improve the the the rain resistance or the trating amongst these there may be mentioned fatty casein or The agents according to the invention can be used by themselves or together with customary biocidcs for combating especially with fungicides or The concentration of the agents employed can vary within wide limits depending on the nature of the It is in general per cent by weight to 20 per cent by for more dilute whilst more concentrated agents contain 20 per cent by weight to 98 per cent by of active Very highly concentrated preparations be used in the ULV technique with minimal amounts of ULV technique is used with extremely finely atomising spray preferably the aid of In combating representatives of the order the following can especially be amongst the range of for use with the active tances of formula Chlorobenside Pluorobenside phonate propanecarboxylic acid and The following Examples illustrate In the two manufacturing Examples which the parts denote parts by weigh E x a p l e 1 240 parts of are dissolved in 1000 parts by volume of and mixed with 180 parts of potassium carbonate and 10 parts of dered potassium After one hour 140 parts of pargyl bromide are added and the mixture heated for hours under After dilution with ice the reaction product is taken up in ether which is washed with dilute sodium hydroxide solution and After evaporation of the ether the end product remains and is recrystallised from ethanol with the addition of ligroin point p 2 Manufacture of the of 4J A consisting of 45 parts of 85 potassium 30 parts of water and 100 parts of alcohol is added dropwise at whilst to 130 parts of in 100 parts of allyl After two hours the mixture is poured onto ice and the end product recrystallised from melting to The following compounds of formula IV can manufactured in the same manner as described in one of 1 or TABLE I Physical 24 cyclohexyl 25 cyclohexyl 3 26 cyclohexyl 27 29 sec 31 cyclohexyl 33 cyclohexyl 34 35 3 36 isopropyl H 37 isopropyl 3 38 39 40 41 cyclohexyl 42 3 butyl 44 46 47 isopropyl 48 isopropyl 51 Equal parts of an active substance according to the invention and precipitated silica are finely Dusting preferably containing of active can be ctured therefrom by mixing with kaolin or In order to manufacture a spraying the following coiponents are for example mixed and finely 50 parts of active substance according to the invention 20 ts of adsorbent 25 arts of Bolus alba kaolin parts of Easily soluble active substances can also be formulated as an emulsion concentrate according to the following 20 parts of active substance 70 parts of xylene 10 of a mixture of a reaction product of an phenol with ethylene oxide and calcium are On dilution with water the desired centration a sprayable is Granules g of one of the active substances of formula I are dissolved in 100 ml of acetone and the acetone solution thus obtained is poured over 92 g of granulated Attapulgite The whole is well mixed and the solvent is stripped in a rotary containing of active substance are E x a p 1 e against spider Bush plants in the leaf stage are infected 12 hours before treatment with the active by placing attacked pieces of leaf from a culture on the so that after thi3 time a population in all stages of development is present on the The plants are then sprayed with the e fied active substance with the aid of a chromatography iser until a uniform de osit of dro lets is leaf After 2 and the results are the parts of the plant are inspected under a scope in order to calculate the mortality percentages action on eggs is not ascertainable after 2 days with this since the average hatching is not yet accurately known at this point in The Table which follows gives the mortality percentages of the normally sensitive variety Koch and the mortality percentages of the phosphoric acid variety telarius Compound 9 serves as the active Action a ainst TABLE II M o r t a y after 2 days after 7 days introduced into a glass tube and dipped for 1 to 2 in 2 ml of an aqueous emulsion of series of 5 and 1 ppm of test after the test solution is removed and the container closed with a cotton wool After days 100 mortality found at the following limiting Compound 5 ppm Compound 10 ppm Compound 8 10 ppm insufficientOCRQuality

Claims (11)

$3 55 -jg What we claim is:

1. A method of combating pests of the order Acarina which comprises applying thereto or to the habitat thereof a compound of the general formula I wherein R^ represents a methyl, isopropyl, sec. butyl, tert. butyl, cyclohexyl or cyclopentyl residue, represents a hydrogen atom, an optionally halogen-substituted alkyl or alkenyl residue having at most carbon atoms or an alkynyl. residue having at most carbon atoms or a phenyl residue which is optionally substituted by one or more halogen atoms or a nitro group, and represents a hydrogen atom or a methyl group.

2. A method as claimed in claim 1, wherein the active ingredient is a compound of the formula la wherein R^ represents a methyl, isopropyl, sec butyl, tert. butyl, cyclohexyl or cyclopentyl residue, R'2 represents a halogen-substituted alkyl or alkenyl residue or unsubstituted alkenyl residue having at most carbon atoms or a phenyl residue which is optionally substituted by halogen or nitro, and R-^ is a hydrogen atom or a methyl group. 33455-2

3. A method as claimed in claim 1, wherein in the compounds of the formula I R^ represents a methyl, isopropjrl, sec. butyl or tert. butyl residue, Rg represents a hydrogen atom or a methyl group, vinyl, chlorovinyl or ethynyl group, and R^ represents a hydrogen atom or a methyl group.

4. A method as claimed in claim 1, wherein the active ingredient is a compound as described in Example 1 or 2 or in Table I herein.

5. A method as claimed in claim 1, wherein the active ingredient is a compound of the formula

6. A pesticidal preparation which comprises as active ingredient a compound of the formula la as defined in claim 2, together with a carrier.

7. A pesticidal preparation, which comprises as active ingredient the compound of the formula given in claim 5, together with a carrier.

8. A pesticidal preparation as claimed in claim 6 or 7> wherein the carrier is a solvent, diluent, dispersing agent, emulsifierjf, wetting agent, adhesive or thickener or a futher pesticide.

9. · A pesticidal preparation as claimed in claim 8, 83455- wherein the further pesticide is N' - (4-chloro-2-methylphenyl) Ν,Ν-dimethylformamidine.

10. A compound of the formula la as defined in claim 2.

11. A compound of the formula