IL30136A - Fungicidally active 1,3,4-thiadiazoles - Google Patents

Description

ACTIVE D The present invention is concerned with new thiadiazoles and with their manufacture and The present invention provides compounds of the general formula in which R and which may be identical or each represents an alkyl group with at least 2 that may be The new compounds of the present invention have a fungicidal action which makes them suitable or combating fungi causing diseases in the present invention also provides a fungicidal preparation which comprises one or more as defined in admixture or conjunction with a The present invention further provides a method of controlling phytopathogenic wherein a plant or a crop area is treated with a or a fungicidal preparation as defined Compounds having a specially good fungicidal action are those in which the groups represented by R and are identical or different and are or branched alkyl groups containing 2 tp 8 carbon of which the following may be mentioned by wayof ethyl and on up to and compounds possess remarkable fungicidal properties For they have a very broad of activity and may be fo combating a wide for example example Venturl s and the cause of downy mildew in grape vines The of these preparations surpasses even that f which s a hitherto known fungicide being illustrated by experiments described i The new the present invention may be for example by the treatment of a compound of the general formula II II s in which and the meanings given with an oxidizing agent at a temperature within the of from about to desired in the presence f a This process may be carried out as of hydrogen peroxide slowly added dropwise to a solution of a group of which may be halo in ml of glacial acetic and 100 ml of acetic anhydride at approximately The batch is for several hours allowed to stand poured ice the product is isolated by suction Other suitable oxidizing agents are substances for example percarboxylio adds or inorganic substances for example potassium permanganate nitric acid and chromic able reaction media are for example either acetic and acetone or acid and sulphuric As stated above the reaction proceeds at a temperature within the range of from about 10 C 120 it proceeds easily within the range of from about to AB examples of the fungicldally compounds of the present may be mentioned the Name of compound Physical constant t ulphony thi hi s ulphony hi adi azo le 2 th adi Name of compound Physical constant 69 TO C 1 3 d 1 azo 77 82 o sulphon l 1 86 C i thy sulphony 113 C Λ sulphonyl e Name of compound Physical constant 81 C thy sulphon 2 104 C thy 91 83 C nD C active principles of the present Invention may be used mixtures several active principles may be other cereal dressings or other pest substances may be depending on the purpose for which ethyl sophorone and solid carriers for other as as natural or substances suitable for the there may b for salts salts of alkylated acid amides and the therep and ox and When the active principles are to be used as may be fpr example new and other in order to the dressed seeds a clearly isible The amount of active principle or principles present the fungicidal preparations may vary within wide exact concentration depending mainly the rate at which the preparation applied to plant pr The preparations for between about 1 by preferably about 20 to by of active and about 99 to by weight of liquid or solid carrier desired or virtue of the potent activity of the new compounds the present la observed that smaller of the new fungicidal preparations are required to achieve adequate control as compared with hitherto Othe for example may added the preparatlona other pests are to be combated at the same good fungicidal action of the fungicidal preparation the presen Invention is illustrated the following Example The action of fungicidal preparations of the present invention against phytopahthogenlc fungi was tested on artificial nutrient media in Petri dishes in each was as nutrient medium consisting malt extract and Of powder was Before the nutrient medium solidified the active principles added and thoroughly mixed in so that the nutrient medium in each Petri dish contained 10 parts of active principle per million parts The medium was inoculated afte it had the of the orming the petrl Inoculated a platinum loop containing the case of fungi that do not for for example and pieces of mycelium having a diameter mm were Assessment was made by e e t e cu ture the fun that do test of fungi Bo 10 10 10 10 10 10 ppm ppm ppm ppra 2 0 0 0 0 0 10 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 ethanesulphQn 0 0 0 0 ff 0 thladlaaole 0 0 0 0 0 49 0 sulphonyl ethaneeulphon thiadlazole 0 0 0 0 0 60 0 e thladlazole 0 0 0 0 0 65 0 e sulphon 10 10 10 10 10 10 10 ppm ppm Ppm ppm ppm ppm lpr o s thladlazole 0 0 0 100 0 sulphon su 0 0 0 0 32 0 thy sulphonyl sulphonyl 3 thl adl azo le 0 0 0 0 36 0 sulphonyl 0 0 0 0 loo 54 0 thladlazole 0 0 0 0 0 0 th sulphonyl sulphonyl 3 0 0 0 0 0 11 0 sulphonyl sulphonyl 0 0 0 41 18 0 0 0 0 0 62 0 0 su eulphon h 29 0 0 0 0 lphony 4 thladlazole 11 0 0 0 60 0 50 44 61 100 42 Coilectotrlehum cbnsortlale Example A spore germination test carried th to he tested was suspended doubly distilled water introduced into a paraffin ring having a diameter of 10 on a slide Each suspension was then inoculated with a loop containing 200 spores i the of apple The lengths of the strings of conidla were measured in after 48 Snore germination test Compound Venturl adi 0 19 0 12 Compound oonldla 1 ppm ppm t hi adi azo 0 16 a n 1 0 22 he 1 le 0 0 t sulphon l 0 0 hep a le 6 19 100 untreated 100 The efficacy of the compounds was tested on the cause of downy mildew grape Both aides of the leaves were sprayed h suspensions of compounds in concentrations of of active ciple per million pa After the spray had the plants were infected with a sporangium suspension o f the fungus and placed Conditions for 24 the were again placed moist conditions enable the to grow out on the underside of the leaves extent of the growth is indicative of the fungicidal The degree of on the control considered to be The degree of Infestation on treated with preparations under test la nopara ltloola vines Infestation as a percentage Compound 500 ppm 2 thi 0 sulphonyl mo e sulphon 0 sulphon thi adlazole 0 t nane azo e 0 3 adl azo le 0 0 sulphonyl thi adlazole 0 adl 0 azole 0 t y p 0 Compound 500 ppm 0 sulphonyl 0 0 sulphonyl 0 2 sulphonyl 0 0 0 0 0 0 0 0 0 0 0 thiadiazole 0 Zineb 1 Control 100 The three Examples Illustrate the surprisingly good effect of the preparations of the present invention as with the hitherto known shows their groat superiority by the fact that the growth of completely Inhibited at a concentration 500 this not being the case with It la in the case of that it is essential for of the fungus to be killed in rder to achieve adequate because only a amount of live fungus can cause the result that growth and crop are insufficientOCRQuality

Claims (1)

1. we claim A compound of the general formula which R and which may he identical or each represents an alkyl group with at least 2 that may be sulphonyl thane f f thy opa sulphonyl thane su Iphony 13 sulphonyl sulphonyl au Iphony 1 ho sulphon 1 b2 ane sul thy s u Iphonyl t sulphon t sulphon sulphon s bu h 2 suXphony in which and each represents an group with at least 2 that may be wherein a compound of the general in which R and have the meanings given is treated with an oxidizing agent at a temperature within the range of from about 10 to 120 A process as claimed in claim wherein the treatment is carried out at a temperature within the range of from 80 to 120 A process claimed in claim to wherein the treatment is carried out the presence of a A process as claimed in any one of claims wherein the oxidizing agent is hydrogen a percarboxylic nitric acid or chromic 37 process as claimed in claim and conducted substantially as described A fungicidal which comprises a of the general ormula R C in which R and each represents an alkyl group with at least 2 that may be halogea admixture or a fungicidal preparation as claimed which or more of the general formula defined A fungicidal preparation which the thiadiazole claimed in any one of claims 2 to in admixture or conjunction with a A fungicidal preparation claimed in any one of clalma o wherein the concentration of the the preparation containa one or the total concentration of the if contains more than defined in claim le within the range of from about 1 to b A fungicidal preparation aa claimed in wherein the concentration or total concentration is within th range of from about 2Θ by one of the fungicidal preparations as claimed Claim and substantially described in Example 3 A method of controlling phytopathogenlc wherein seeds are treated a compound as claimed in claim method of controlling wherein seeds are treated the compound claimed any one 2 method of controlling phytppathogenic fungi wherein seeds are fungicidal as claimed in an one of to A method of controlling phytopathogenlc a plant is treated h compound aa claimed in m i A method of controlling fungi wherein a plant treated the compound claimed any one claims to of controlling a plant treated a fungicidal preparation as claimed any of claims Λ claimed claim and conducted substantially as described A method Of controlling fungi with compound as claimed clai method controlling phytopathogenle wherein a crop area with the compound claimed in any one of claims 2 to A method O controlling phytopathogenlc a area with a fungicidal preparation as claimed any one of claims to insufficientOCRQuality