IL23650A - Benzofuranyl carbamates and pesticidal compositions containing them - Google Patents

Description

l and pestlcidal compositions containing them FISONS PSST 22724 invention relates to certain carbamates as hereinafter which have been found to possess to their preparation and to pestioidal compositions containing the It has that the carbamates hereinafter described are active as pesticides and and certain of them are particularly active against eaterpillare and a high level of Accordingly the present invention is for the benzofuranyl carbamates of the one of the groups and is in which is an alkyl group example of carbon atoms as methyl or and hydrogen or an group example of carbon atoms as methyl or and the remainder of the groups anal are halogen example chlorine or or alkyl example methyl or and and are the same or different and are hydrogen or lower alkyl example of carbon atoms such as methyl or with the proviso that formula is a group and and are all must not bo a methl rou The present invention is also for a process for the preparation of the benzofuranyl carbamates as defined above whioh oomprxses reacting the corresponding hydroxybenzofuran and an isocyanate or reacting the corresponding benzofuranyl 7 8 7 8 formate and an amine of the formula H and by reacting the corresponding hydroxybenzofuran with a chloride of the formula The present invention is also for a pesticidal composition which oontains as an active ingredient a benzofuranyl carbamate as identified The present invention is also for a pesticidal composition which contains a benzofuranyl oarbamate as identified above and at least one of the materials comprising wetting solid solvents high boiling and edible substanoes attractive to The present invention is also for the treatment of areas the and materials susceptible to attaok by which comprises applying thereto or incorporating therein a pestioidal composition as identified The materials susoeptible to attaok by pests include materials such as fabrics and textile According to a preferred the present invention is for the benzofuranyl carbamates of the X Y where and R are seleoted from hydrogen and alkyl example methyl or one of the groups X and Y is 16 where R is an alkyl group example methyl or and R 16 is hydrogen or an alkyl group example methyl or and the other is hydrogen or an alkyl group example methyl or and R R R and R are all or R 12 and R 13 are when there is a double bond between the oarbon atoms of positions 2 and 3 benzofuran According to a further preferred the present invention is for the benzofuranyl carbamates of the formula where R 15 is an alkyl group example of 1 carbon atoms 16 such as methyl or and R is hydrogen or an alkyl group example of carbon atoms such as methyl or According to another preferred the present invention is for the benzofuranyl carbamates of the formula where is an group example of carbon atoms 16 such as methyl or and E is hydrogen or an group example of carbon atoms such as methyl or According to a further preferred embodiment the present invention is for the compounds and and their use as These oompounds have been found to particularly active against oaterpillars and with a high degree of In pestioidal compositions the benzofuranyl carbamate may be incorporated for example with solid inert media comprising powdered or divided solid for example clays such as china fertilizers and the such products either comprising dust or larger particle size materials It is preferred however to mix the benzofuranyl oarbamate with a wetting with or without the incorporation of powdered or divided solid materials as referred to so that a wettable product is obtained which is capable of use as such or as a suspension or dispersion in If desired the benzofuranyl carbamate may be incorporated with an organio which may be for example a high boiling together with a wetting or dispersing agent so as to form an emulsifiable liquid concentrate which may be dispersed in water for spraying The TOtting agents used may comprise anionio oompounds such as for fatty sulphate esters suoh as dodecyl sodium fatty aromatic sulphonates suoh as sulphonates butyl naphthalene more complex fatty sulphonates such as the amide condensation product of oleic acid and taurine or the sodium salt of dioc yl succinic The wetting agents may also comprise wetting agents suoh as for example condensation produots of fatty fatty alcohols or fatty substituted phenols with ethylene or esters and ethers of sugars or polyhydrio or the produots obtained from the by condensation with ethylene or the products known as block copolymers of ethylene oxide and propylene The wetting agents may also comprise cationio agents suoh as for example oetyl thyl mmonium and the like The pesticidal compositions according to the present invention may contain edible substances attractive to insects such as mollasses and protein Such compositions suitably also contain specific inseot The pestioidal compositions according to the present invention in addition to the benzofuranyl carbamate other pesticides suoh as insecticides example or molluscicides and The following examples are given to illustrate the present the parts and percentages are by weight unless otherwise Example 1 To a solution of parts of in 100 parts of diethyl ether were added parts of methyl isocyanate and parts of trie lamine The solution was left to stand for 1 hour and then evaporated to low bulk 10 and diluted with parts of light petroleum point 2 to give 8 parts of the crude melting point This crude product was recrystallised from the same solvents to yield 5 parts of l amate melting point Analysis 2 Example 2 To a solution of 10 parts of in 20 parts of diethyl ether were added 5 parts of methyl isooyanate and parts of The solution was left to stand for 1 hour and then diluted with 5 parts of light petroleum point and a precipitate This was filtered off and recrystallised from the same solvents to yield parts of melting point Analysis Example 3 Using the method described in Example dihydrobenzofuran and methyl isooyanate were reacted together to give melting point 61 requires Example 4 Using the method desoribed in Example and methyl isooyanate were reacted together to give melting point Analysis Found Examples 5 1 In an analogous way to the preceding examples the following compounds were 88 127 I 3I 155 147 149 2 me any 1 148 me uranyl 116 1 Example 12 To a cooled stirred solution of anhydrous thy lamina in isopropyl ether was added a solution of uranyl chloroformate in benzene over a period of 15 keeping the temperature below The mixture was then washed with dilute hydrochloric acid and then with water until the washing were The organio layer was dried with sodium sulphate and the solvent removed by Fractionation of the residual oil produced benzofuranyl lc as a colourless boiling point which solidified to a yellowish melting point Examples 13 The following were prepared by analogous methods to that of Example 71 49 oily Example 17 9 oentimetres diameter glass plates were treated with an acetone solutions of each of the compounds thylcarbamate and to give even deposits equivalent to foot and 100 At ten day adult houseflies domestical were oonfined to these surfaces for 24 hour after whioh mortality was It was found that with both both rates of application gave kill of houseflies and 60 days after Example 18 Young cabbage plants with true leaves were sprayed with aqueous acetone solutions of containing and of the At intervals after second instar larvae of the cabbage white butterfly were confined to the plants using electric barriers for a period of 48 after which mortality was The results are tabulated Kate of Applioation Age of Deposit Mortality 1 day 3 days 100 7 days 94 10 days 75 1 day 100 3 days 100 7 days 48 Example 19 9 oentimetre diameter filter papers treated with aqueous acetone solutions of each of the and methylcarbamate at rates equivalent to 1000 and 100 milligrams per square foot were plaoed in the bottom of 9 oentimetre diameter Petri Batches of adult female houseflies lightly anaesthetised with carbon dioxide were then introduced into the dishes and a glass lid plaoed over After 24 hours the flies were examined and it was found that 100 of those treated with each compound at both rates of had been Example 20 7 oentimetre discs of cabbage leaves were with 1 millilitre aqueous acetone solutions of each of the compounds identified below at concentrations equivalent to leaf applications of 1 and pounds of active ingredient per After each leaf disc was placed in a 9 oentimetre diameter Petri infected with ten seoond larvae of the cabbage white and covered with a glass Three replications were made of eaoh concentration After hours the larvae were examined and the number dead were Percentage mortalities are tabulated Example 21 A wettable powder was made up as follows The sulphated 1 oxide condensation product wetting agent commercially available as HOE 4 The sulphonated condensation product wetting agent commercially available as DIAP0L PT China olay This product was readily dispersible in water for spraying insufficientOCRQuality

Claims (1)

1. composition contains active ingredient a carbamate of of the groups is which is an and or an the of groups or are the group hydrogen and lower alkyl and are or both there feeing a double bond between the with the that where the group and are not be 4 pestloidal as claimed in 1 which lso contains at least one selected from the group comprising solid edible substances attractive to and other pesticidal composition substantially as hereinbefore A process for the treatment of areas and which contacting them with a composition as claimed in any of the preceding The carbamates of the wherein of the groups R R and R is Θ in which is an alkyl group and R is hydrogen or an 3 alkyl the remainder of the groups R and alkyl are hydrogen or lower alkyl groups and and are both hydrogen or both there is a double bond between the carbon with the proviso that where s is the group and are 14 must not be fhe benssofuranyl carbamates of the 10 where R and are hydrogen or alkyl one of the groups X and is where is an alkyl group and is hydrogen or an alkyl and the other is hydrogen or an alkyl and and are all hydrogen or are when there a double bond between the carbon A ι The carbamates of formulae group is hydrogen or an grou The carbamates of the wherein an group and is hydrogen or an A process for the preparation of a benzofuranyl carbamate according to Claim which comprises reacting an 7 of the or a of 78 the formula with a of the of and is of and as a A process for the preparation according to Claim 1 which an ft amine of the formula with a benzofuranyl chloroformate of the 3 wherein one of the groups R R R and is a 1 2 group and the remainder of the groups R R R in for the preparation of carbamates according to Claim 1 substantially hereinbefore described and illustrated PCsea insufficientOCRQuality