IL40476A - O,s-dialkyl-o-phenyl thiophosphoric acid esters,their manufacture and their use in pest control - Google Patents

Description

ona Hew enyl thiophoaphoric acid their manufacture and their use in pest control 38479 t This invention relates to acid esters of the formula wherein X is hydrogen and Y chlorine or X is chlorine and Y Another subject is the manufacture of the of formula I and their use as active ingredients in pesticidal especially ihsecticidal The compounds of formula I are most generally disclosed in French Patents and 1 567 corresponds o Israel patent specification The DOS discloses and The instant compounds have a similar spectrum of activity but are surprisingly more A disclosure of even more closely related compounds such as the and acid ester is to be found in the DOS corresponds to Israel patent ification Accordingly the are selection out of the latter and show surprisingly superior activities on at least the same toxicity level as the closest known especially with respect to their initial effect towards cotton The new thiophosphoric acid phenylesters may be prepared according to known processes such acid j In the above formulae Me represents an alkali particularly or ammonium or R stands for a especially methyl or ethyl and Hal is a halogen atom such as iodine especially however chlorine or As acid binding agents there may be used tertiary tria kylamines pyridine or dialkylanilines also suitable are inorganic bases such as carbonates and bicarbonates of alkali and alkaline earth Depending on conditions it may be desirable in order to enhance the yield or reduce the duration of the reaction to use a catalyst as copper or copper he processes la 3b are out at a reaction temperature between and at normal pressure and in solvents or diluents inert to the Suitable as inert solvents or diluents are for example ethers and ethereal compounds such as diethyl dipropyl amides such as ic acid aliphatic and aromatic which may be halogenated particularly chlorobenzene nitriles such as aceton For processes 3a and 3b alcohols such as or isoprupanol are uncfe of I broad insect and cidal activity against plantp thogenic peats being compounds above all as contact poison and thus can used for the control of all velopment stages such as pupae and adults of chewing d boring posts and Noxious viduals of this kind are to be found in the field of forest and stored products Most results how ver are achieved against pests noxious to cotton and this connection the following families of insects and acarina must be Chrysomel idae ionidae enebr idae Ilyponomeutidae Lymantri threut i dae ranychidae insecticidal acaricidal effects can bo broadened and matched to given cumstances by the addition of other insecticides or aca icides Such additional active ingredients may be selected from the group of nitrophenols and derivatives chlorinated pyrethr inlike compounds and amid especially formamidines a most valuable of which is 1 2 i The compoundjof formula I may be used as active or together with suitable carriers Suitable carriers and additives may be solid or liquid and correspond to he substances in Lion as wetting ad binders application the instant m be processed to ventionally formulated preparations as they are commonly application te may be used as concentrates or lutions according to the of such parations are in solid scattering agents or granules in liquid concentrates of active ingredient dispersible in wettable pastes or emulsifiabie solutions above pesticidal preparations may be manufactured in known manner by intimately mixing grinding the active dient with the suitable optionally with the addition of dispersants or solvents which are inert towards the active To manufacture dusts and scattering the active substance mixed according to known methods with solid Suitable carriers for ground precipitated alkaline earth and potassium aluminum silicates and and magnesium magnesium ground for example ammonium ammonium ground vegetable as corn bark nutshell cellulose residues of plant activated charcoal granular formulations can be easily manufactured according to known To these mixtures may also be added stabilizers for the active ingredient anionic and cationic surface active which for example improve the adhesion of the active ingredients on plants or parts of plants and ensure a better wettability and dispersibility Suitable additives are for example cellulose derivatives carboxymethyl hydroxyethyl glycol ethers of monoalkyl and dialkyl phenols having 5 to 15 ethylene oxide radicals per molecule and 8 to 9 carbon atoms in the alkyl lignin sulfonic their alkali metal and alkaline earth metal polyethylene glycol ethers fatty alcohol polyethylene glycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol condensation products of ethylene polyvinyl pyrrolidones polyvinyl condensation products of urea and and also latex The concentrates of the active substance wettable pastes and emulsifiable are agents which can be diluted with water to any concentration They consist of active optionally additives which stabilize the active substance and agents silicone optionally Suitable additives are well known in the formulation technique and the manufacture of the concentrates is achieved by known I dissolved in a suitable organic solvents or in Such solvents are well known in the formulation The content of active substance in the above described prepara tions is between to and most preferably between 2 and In this connection it should he that if the application is carried out from aircraft or with some other suitable it is possible to of up to or even pure active The application rate of active ingredient on the other hand is as a rule about to kg per active substancesof formula I for be formulated as Dusts The following substances are used to manufacture a and 5 parts of active ingredient 95 parts of talcum 2 parts of ingredient 1 part of highly disperse silica 97 parts of The active ingredient is mixed with the carriers and Granules The following substances are used to produce 5 parts of active ingredient parts of epichlorohydrin parts of cetyl polyglycol ether parts of polyethylene glycol 91 parts of kaolin size The active substance is with and dissolved with 6 parts of the polyethy glycol and cetyl polyglycol ether then The thus obtained solution is sprayed on to and the acetone subsequently evaporated in lettable The following constituents are used for the preparation of and a and a 40 parts of active substance 5 parts of sodium lignin sulphonate 1 part of sodium dibuty halene sulplionatc parts of silica 25 parts of active substance parts of lignin parts of Champagne cellulose ture parts of sodium dibutyl naphthalene sulphate parts of silica acid parts of Champagne chalk parts of 25 parts of active substance parts of isooctylphcno parts of Champagne parts of sodium aluminium silicate q parts of 46 parts of kaolin 10 parts of active ingredient 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphates 5 parts of naphthalenesttlphonic condensate 82 parts of The active ingredient is intimately in suitable with the the mixture being then ground in an appropriate mill and Wettable powders are obtained which can be diluted with water to give suspensions of any desired The following substances are used to produce a a and a emulsifiable 10 parts of active ingredient parts of epoxidised vegetable oil parts of a combination emulsifier consistingof fatty alcohol polyglycol ether and sulphonate calcium salt 40 parts of parts of 25 parts of active ingredient parts of epoxidised vegetable oil 10 parts of an alcohol polyglycol ether mixture 5 parts of dimethylformamide parts of parte of calcium 20 parts of cyclohexanone 20 parts of xylene From these concentrates it is possible to by dilution with emulsions of any desired The fallowing substances are used to ure a and 5 parts of active ingredient 1 part of epichlorohydrin 94 parts of petrol range 95 parts of active ingredient 5 parts of epichlorohydrin following examples illustrate the and testing of the compound according to the present Example 1 g were dissolved in 150 ml benzene and g triethylamine were then At g of were added dropwise with continuous Stirring was then continued for 12 hours at room The mixture was washed with solution and water and dried over anhydrous sodium The benzene was distilled off and the residue purified by distillation 49 g of the ester of the formula 20 was obtained with a refractive index The compound of the formula was made in analogous 2 Pott d cotton and tobacco plants respectively were 125 of active ingredient in the form of si er the coating had the treated plants were w t third instar larvae of lleliothis The tests were running under greenhouse conditions at and 60s relative humidity Assessments to evaluate the initial effect of the ate acitivity of the active ingredient were carried out 24 and 48 hours after the infestation of the plants with the Lest plan i h the individuals 2 and 8 days after the of the active test was nd compounds C o Y A test analogous to that described under was accomplished by spraying the plants with 500 ppm of active ingredient in the form of an aqueous Assessments to evaluate the initial effect of the activity over a prolonged period were carried out as the coated test plants were infested with the test individuals 8 days after the application of the active ingredient and checked 4 and 24 hours after the compoun s In this test too compounds I and III clearly show a better initial vulgaris had an infested of leaf a mass culture of Totranychus urticae placed on them 12 re test for the acaricidal occupying mobile were sprayed with the emulsified testing preparation Ί p n Γ L In this test too I and clearly show a better initial vulgaris had an infested piece of a mass culture of urticae on 12 t test for the occupying were sprayed with the testing preparation i a chromatography atomiser so that the sprayed layer did not run The number of living and dead adults and eggs were evaluated after 7 days under a stereoscopic microscope the result expressed in During the the treated plants were kept in greenhouse compartments at 2 The evaluation was of the test proved qood activity of the active 4 Λ dust on a base of talcum and containing active ingredient was applied to filter paper in concentrations of 2 and of active substance per m Onto each of the treated substrates were applied 5 Necrobia Rhyzoperta Anthrenus vorax and Tribolium confusum individuals respec Lively Evaluation took place 24 hours Test compounds were same as set forth in Example insufficientOCRQuality

Claims (7)

V/1LAT MB CLAIM IS; 40476 2 '

1. A compound of the formula wherein X is hydrogen and Y chlorine or X is chlorine and Y bromine . compound according to claim 1 , 1» /

CI

3. The compound according to claim 1

4. A proceea for the preparation of a compound according claim 1 which compriaea reooting, in the presence of an id binding agent, a halophosphate of the formula with a phenol of the formula or with a phenolate of the formul wherein X and Y have the meaninga given in olaim 1 and Me ia an alkali metal, ammonium or alkylammonium group.

5. A peat control agent which cornprioes aa active component a compound according to any of claima 1 to 3 together with suitable carriers and/or other additivea.

6. A method of pest control against insects and representatives of the order Acarina which comprises applying to the said pests a pesticidally effective amount of a compoun according to any of claims 1 to 3.

7. A method according to claim 6 which comprises controlling insects harmful to cotton and vegetables.