IL34963A - Benzimidazole derivatives,their preparation and their use as pesticides - Google Patents

Description

their preparation and their AM invention is concerned with derivatives of formula as well as with the use thereof as active ingredients in biocidal In formula I and in the and which may be the same or are chlorine or bromine or straight or alkyl or alkoxy groups having 1 to 4 carbon is an alkyl group having 1 to carbon atoms or an allyl is a straight or alkyl group having 1 to 17 carbon atoms optionally substituted with 1 to 3 halogen atoms or with a groupi a phenyl an alkenyl group having 2 to 17 carbon atoms and up to double or an alkoxy group having 1 to 12 carbon The compounds according to the invention may be produced in line with known for instance by reacting a benzimidazole derivative of general formula with a compound of formula where and have the meanings indicated above represents a group which is easily removable as an such as a chlorine or bromine an an a benzoyloxy a trlfluoroacetoxy an or alk The reaction is performed within a suitable solvent or mixture of for example in or chloroform at temperatures between 0 and preferably at room It is required to perform the reaction within a homogeneous as the starting compounds of general formula II are partly only difficultly soluble the solvents in The reaction is being performed appropriately in the presence of an acid preferably a tertiar aliphatic The obtained final products mostly solid which tend to form solvates with the solvents used for production or Several of the compounds according to the inventio are As as the compounds are they mel decompose mostly in the range between 140 180 The readil amorphous products between 60 120 The starting materials are being produced in line with known The compounds according to the invention are effective in low against a great number of phytopathogenio powdry mildew such as Erysiphe graminis and Podosphaera against rost such as Puccinia recondite and Uromyces against such as phytophthora infestans and Alternaria against Venturia inaequalis and The novel compounds are systemic which may have prophylactic as well as curative They may also be used as ovicides and The wherein means a For the production of pesticides the active ingredients according to the invention are prepared in the usual way using excipients and such as suspension emulsion sprays fungicides or Due to the systemic action of the novel a formulation as fungicide is often of special in this manner a long lasting effect may be obtained in many Many of the active ingredients according to the invention may be formulated to when diluted with water form stable which in comparison with the benzimidazole fungicides already of related an important as the latter cannot be formulated in the wa indicated The content of active ingredients of pesticides with the compounds according to the invention amounts from to 80 For are if dilutions up to ah active ingredient concentration to dusting agents ul olume have a content of active Examples 5 parts by weight of a compound according to the invention 5 parts by weight of synthetic silicic acid 90 parts by weight of talcum The ground mixture of active ingredient and silicic acid is mixed with talcum finely Emulsion 10 parts by weight of a compound accordin to the invention 50 parts by weight of dimethylformamide 40 parts by weight of glycol 10 parts by weight of Lutensol AP 10 product of and 10 of The liquid concentration is diluted with water to a sprayable liquid of the desired concentration for of an active of to percen by Spray parts by weight of a compound according to the invention parts by weight of sesame oil parts by weight of parts by weight of Prigene The mixture of the indicated components serves for use of the active ingredients according to the invention in form of Suspension Powder 80 parts by weight active ingredient according to the invention 8 parts by weight of 5 parts by weight of colloidal silicic acid 5 parts by weight of sodium sulfate 2 parts by weight of The mixture of the components is suspended in For use suspensions with preferably to percent by weight are to be The production of the active ingredients aocording to the invention is illustrated by the following 7 EXA PLE 1 2 ethyl ole To a suspension of g of pulverized in ml of dry pyridine a solution of g of in 20 ml of is Subsequently g of amine are dropped into After having stirred for 14 hours The filtrate is diluted with 450 ml of A crystalline e filtration after is washed with methanol and dried at C N EXAMPLE 2 ethyl Into a mixture of g of g of amide 100 ml of dry t trahy rofuran 4 g of triethylamine are The suspension is stirred for 70 hours room temperature and The filtrate evaporated in vacuo yields a solid which is recrystallized from 178 There are being produced 2 carbonylamino 167 ethyl crystallizes If the compound is recrystallized from l mol ethyl The crude product is recrystallized from The compound with isopropanol is a crystalline 172 ethyl The amorphous crude product is dissolved in After 24 hours the compound crystallized with 1 mol of crystalline When drying in vacuo at the substance obtained free of at 168 9 ethyl After treatment with the compound is an o obtained 100 110 2 amino From and acid 105 155 ethyl As crude product an amorphous residue is whic is crystallized by treatment with 157 2 ethyl amino The crude product is brought to crystallization according to 142 2 The crude product is crystallization according to 157 10 2 ethyl A crude product is which crystallizes when treated with After recrystallization from the substance melts at becomes solid again and decomposes finally at 2 ethyl carbonylamino Corresponding to from dazole and in the presence of triethylamine The crude product is recrystallize from ethyl 141 ethyl Prom and After recrystallization of the crude product from the compound contains 1 of crystalline At first it melts at then it becomes solid again and finally it decomposes at 11 2 ethyl 173 2 ethyl The product recrystallized from isopropanol contains mol of crystalline The ccdnpound crystallizes from isopropanol as solvate with of o 146 148 2 carbonylamino Prom isopropanol is obtained the solvate with 1 mol of 152 L 2 ichlorophenoxyaoetylamino 2 recrystallization from 2 146 12 ethyl 174 EXAMPLE 3 2 Into g of and 8 g of acid amide in 100 ml of tetrahydrofuran are dropped g of residue is After stirring for 48 hours at room filtered the filtrate is evaporated in vacuo and the residue is triturated with 50 ml of The crystals are sucked off and treated with T 200 ml of the insoluble is filtered off in vacuo and recrystallized from 170 EXAMPLE 4 Into a mixture of g of g of and 50 ml of dimethylsulfoxide are dropped 4 g of the insoluble residue is l ered After havin stirre for 16 consisting mostly of triethylamine 13 The mixed with 200 ml of The separating filtered crystals are washed with water and recrystallized from 149 There are obtained in a corresponding 153 2 166 EXAMPLE 2 In 100 ml of anhydrous g of and g of are dissolved Into the mixture is dropped while stirring g of Stirring is continued for 3 hours a room temperature residue is filtered unreacted the residue consists of A g of and of amine The filtrate is mixed with 500 ml of filtered the precipitate is off and recrystallized from The compound is obtained as solvate with of crystalline 13a Using a procedure analogous to that described in Example the following compounds are r 13b hox pto insufficientOCRQuality

Claims (1)

a of formula wherein represents a group which is easily removable as a anion and has the same meaning as in Claim A method for controlling which comprises applying to the hahitat of the fungi an effective amount of a compound of formula I i Claim 1 or a composition according to Claim Process for the production of pesticidal compositions according to Claim which comprises formulating a compound of formula I in

1. Claim 1 with exci s For the Applicants RTNERS insufficientOCRQuality