IL31770A - Ortho-nitrodiphenyl ethers,their preparation and pesticidal compositions containing them - Google Patents

Description

ort their preparation and compositions present invention provides henyl ethers of the formula in which represents methylthio or methylsulfonyl and represents chlorine or methyls Some important specific compounds according to the invention are those of the formulae Tho compounds of tho general formula can he manufactured known for by reacting a compound of the general formula compound of general formula with In formulae and have the same meanings as in the general formula and is a halogen especially a chlorine may present in a certain after forming the ether is subsequently converted into the desired for as substituent may be subsequently converted by treatment with hydroge glacial acetic acid into the group provided this is possible at a halogen atom may be introduced by subsequent of the corresponding diphenyl These compounds have a very broad activity spectrum against pests of vegetable or animal nature and against They can be used for combating insects in all stages of their and also possess an extensive activity when used for destroying representatives of the order As molluscicides they display a good activity against The nematocidal properties should likewise be The new active substances can also be used in microbicidal for against fungi and cially against phytopathogenic fungi Their primary use is as a not only for killing off plants but also for regulating their Compounds of the formulae to proved especially efficacious in controlling undesired plant growth in cultures of soybeans and grain for maize and The new compounds of the formula can be used by themselves or preferably in the form of preparations together with a suitable for one or more solid fertilizers and other active substances as The present includes such pesticidal The method of formulation of the new compounds in liquid or solid in dry or moist forms as wettable dusting tions or their use in the gas phase application is generally known and has been described in greater detail in Specifications 665 and 3 329 British cation 047 and Swiss Specification In many the application in form of granulates to achieve the uniform of the active substance over a organic causing this solution to be absorbed by a granulated vehicle attapulgite or and removing the whatever form such preparations are they may be used for distribution over large surfaces by dusting or the for with the aid of used as a the preparation contains 5 to 90 of the active The amount in which the preparation is used depends on its formulation and the way in which it is it may range from to preferably from 1 to 5 kg per The Examples illustrate the EXAMPLE 1 A solution of 14 g of and g of powdered sodium hydroxide in 75 ml of dimethylsulphoxide is mixed with g of benzene and the whole is refluxed for 6 hours on an oil bath maintained at a temperature of The reaction mixture is then poured into ice water and the precipitated crystals are filtered off and recrystallized from aqueous to yield g of ether melting at 81 to The following compounds are accessible in an ogous Examples of Formulation Dusting agent Equal parts of an active substance of this invention and of precipitated silicic acid are finely ground When this mixture is mixed with kaolin or dusting preferably having a content of active substance ranging from 1 to can be Spray powders In order to manufacture a spray powder the following for may be mixed and finely 50 parts of an active substance of this invention 20 parts of adsorptive silicic Trade 25 parts bolus alba parts of a reaction product of phenol with ethylene oxide parts of sodium Emulsion concentrate Readily soluble active substances can also be formulated as emulsion concentrates in the following 20 parts of active substance 70 parts of xylene and 10 parts of a mixture of a reaction product of an alkylp enol with ethylene and calcium sulphonate are mixed When this mixture is diluted with water to the desired a sprayable emulsion is EXAMPLE 2 The following types of plant were sown in a Zea Brassica and Amaranthus The testing was carried out by the process with 2 and 4 kg of active substance per The treatment was carried out 1 day after planting and the evaluation 21 days after The results are listed in the following in 1 rio effect with to 9 plant completely As can be seen from the data shown it is possible to with the active substances of this an excellent control of weeds without attacking the useful A similar result is also obtained with compounds and EXAMPLE 3 I In a greenhouse compound 1 has been compared with fluorodifen or known from the US Patent Specification Specification Swiss Specification A aqueous suspension of the substance to be tested was mixed with garden soil so that a final concentration of respectively g and g of active substance per liter soil was The earth was then placed in pots with the following test Triticum Avena Hordeum Zea oryza and with the weeds The pots were then put in a green house and kept at a temperature of and relative humidity in continuous After 20 days the test results were evaluated according to a 10 point 10 plants unaffected as control 0 plants destroyed 9 intermediate stages of The suspension was prepared from a wettable powder of the following compositions 10 parts of active parts of sodium dibutylnaphthyl 10 parts of sodium i aluminium parts of kaolin and 1 part of a densate of naphthalene sulphonic phenyl sulphonic formaldehyde which was diluted with water are by The compound according to the present destroys the weeds while leaving the culture crop Zea and Oryza The compound according to the Patent does not show the same excellent the crop rice gets damaged while the weed Linum is not Example 4 In a test for the the lowing plants have been sown into trays in green Sinapis and An amount corresponding to 4 kg per hectare compounds 4 and have been The treatment was made 12 days after when the plants had reached the The evaluation took place 20 days after the treatment according to the following 1 no e on plant slight reversable as increasing damage The results are summarised in the table below insufficientOCRQuality

Claims (1)

1. CLAIMS of the general formula in which represents or methylsulfonyl and represents or compound of the formula The compound of the formula Compounds as claimed in Claim substantially as described in Example 1 process for the manufacture of ethers according to Claim wherein a phenol the formula is reacted with a of the formula where and have the same meaning as in Claim with deh if with subse uent A modification of the process claimed in Claim phenol reactant is used in which is a after the the reaction product is subjected to oxidation for converting the group into the group Pesticidal preparations which as active a compound as claimed in any of Claims 1 to 4 together with a suitable Preparations as claimed in Claim containing one or more of following a a a an a a fertiliser further A preparation according to Claim substantially as described in Example 1 A method of selectively combating undosired plant growth in cultures of useful plants which comprises applying to the area containing the plants a compound as claimed in any of Claims 1 to or a preparation as claimed in Claims Θ or A method as claimed in Claim wherein the cultures maize or A method as claimed in Claims 10 or wherein weeds are A method according to Claim substantially as described in Example 2 For the Applicants insufficientOCRQuality