IL36057A - P-fluoro-m-trifluoromethylphenylureas,their manufacture and their use for combating pests - Google Patents

Description

their and their peats AG 2 invention relates to new compounds derived from their manufacture and their use as active substances in agents for combating The new compounds are encompassed by the general formula in which lower lower lower lower lower lower or o and together the nitrogen atom to which they are form a t saturated heterocyclic and X is oxygen o lower alkenyl and alkynyl radicals which are possible and respectively contain up to preferably u to carbon These radicals be branched or Preferred alkenyl and alkynyl radicals within the scope of the present invention for and propynyl or The groups which are possible for have 3 to 6 carbon Examples of groups are cyclopentyl and 3 Compounds of particular importance are those formula wherein is hydrogen or a group and is a a preferred representatives of the formula are compounds of the formula wherein is hydrogen or methyl and Rg is or propynyl or As an example of a suitable compound of the formula there may be quoted the where is a methyl or methoxy 4 Herbicidal phenylureas one or more groups on the phenyl ring are known from Israel Patent Specifications 16600 and 17144 and US Patent Speci ication In Israel Patent Specifications 14217 and 16600 describe phenylureas substituted on the phenyl ring with both a trifluoromethyl group a d with one or two especially as havin good herbicidal The compounds of formula I according to the present invention possess this activity and are especially useful for controlling weeds in cultures of The phenylureas of the formula I to IV are novel and can be manufactured accordin to known For by reaction of an aromatic compound of the formula i which A represents the grouping or aryl oxygen or sulphur with a primary or seconda y amine of the formulae 5 in which and have meanings indicated for the formula the two groups A and together being capable of forming the urea by reaction of the aniline of the formula with a compound of formulae or aryl oxygen or sulphur wherein the same meaning formula The compounds of the show a biocidal and can employed for combating vegetable animal They for against all stages of development of such for larvae and The favourable toxicities of the of the formula or agents these should The new compounds furthermore also possess a good micro biocidal activity against especially against pathogenic fungi such as appendiculateo and Puccinia In the concentrations required for this no damage to plants is The compounds according to the invention further possess good activity undeslred plant This is attainable in the and processes and is particularly observed in important crops such as potatoes and the used can vary within wide for example between to 10 kg of active substance per but preferably to kg per are The substances of the formula can be employed by themselves or together with a suitable carrier Suitable carriers and additives can be solid or and correspond to the substances which are customary in formulation such for natural or generated mineral dispersing wetting binders yet other biocidal compounds be Such biocidal compounds to the saturated and unsaturated fatty halogenobenzoic phenoxyalkylcarboxylic organic phosphoric acid quaternary ammonium sulphamic borates or Such compounds Substituted urea Iphenyl urea oxyp 4 0 Substituted isopropylamino triazine thio thio thio th y1 1 n n thio isopropylamino thio mino propionitrile 2 triazine Phenols salts Pentachlorophenol or thereof salts butylphenol salts esters salts esters e stera esters and Esters 2 acid acid and salts acid acid and salts ester Cyclopentanecarboxylic acid 2 ester acid and salts acid and salts acid and salts acid salts 2 ic salts and esters 2 salts and esters salts and esters 2 salts and esters salts and esters salts and esters salts and esters acid acid acid dimethyl ester acid salts and acid salts and esters salts and esters acid acid salts and esters Gibberellic salts and esters Indolylacetic acid Indolylbutyric acid salts and esters N Naphthylacetic acid salts and esters salts and esters Trichloroacetic acid acid salts and esters salts and esters Benzimidoxyacetic salts and esters Ethylene Chloroacetic diethylamide 2 Acid Derivatives acid isopropyl ester acid methyl acid isopropyl ester acid ester acid isopropyl ester 2 Methyl and also molinates and of the general formula S wherein and denote a lower alkyl or alkenyl radical 9 or wherein and together with the nitrogen atom to which they are bonded represent a or optionally alkylated a total of 6 or 7 C being necessary for the groups to be bonded to the carbon atoms adjacent to the nitrogen and represents the or and amongst these especially e and also acid carbamate l hen lcarbamate carbamate Anilidee Cyclopropanecarboxylic acid Cyclopropanecarboxylic acid Cyclopropanecarboxylic acid acid halamic acid Organic Compounds 2 S hiophosphate Various Compounds chloride Maleic acid hydrazide acid sal chloride Ammonium sulphamate hyluracil luracil Sodium Potassium Acrolein Arsenates alcohol 2 Hexafluoroacetone hydrat Cacodyl 2 The agents according to the invention can used in the form of granules or dusting The methods of application depend on the end and ensure that the active substance can be finely To manufacture it is possible to use such as especially for example ethyl alcohol or isopropyl such as acetone or cyclohexanone aliphatic such as and cyclic such as tetrahydronaphthalene and alkylated and also chlorinated such as tetrachloroethane and ethylene and finally also mineral and vegetable oil3 or mixtures of the The aqueous preparations are preferably emulsions and The active as such or in one of the abovementioned are homogenised in preferably by means of wetting agents or dispersing Quaternary ammonium compounds may be mentioned as examples of cationic or dispersing sulphuric acid sulphonic and alkoxyacetic acids may for example be mentioned as anionic and polyglycol ethers of fatty alcohols or ethylene oxide condensation products with lphenols may be mentioned as On the other it is also possible to manufacture concentrates consisting of active emulsifier or dispersing agent and solvents if Such concentrates be diluted with before Dusting agents can firstly be manufactured by or conjoint grinding of the active substance with a solid Possible solid carriers for example diatomaceous calcium boric acid or tricalcium but also cork charcoal and other materials of vegetable On the other the substances can also be absorbed on the carriers by means of a volatile Pulverulent preparations and pastes can be made capable of suspension in and usable as spraying by adding wetting agents and protective In many the use of granules for the uniform release of active substances over a longer period of time is of These granules can be manufactured by dissolving the active substance in an organic absorbing solution by a granular for example attapulgite or and removing the They can also be manufactured by mixin the active substances of the formula with polymerisable after which a polymerisation is carried out which leaves the active substances the granulation being performed whilst the polymerisation is still The content of active substance in the agents described above is between and it should be mentioned that in the case of application from aircraft or by means of other suitable application concentrations of up to or even pure active are Example A solution of g of phenylisocyanate in 80 ml of dry acetonitrile was added dropwise at room with vigorous to a solution of ml of strength dimethylamine in ml of After completion of the the mixture was stirred for a further after which the active substance 1 of the Melting crystallised out on dropwise addition of The following compounds were also manufactured 3 19 20 Example Equal parts of an active substance according to the invention and of precipitated silica are finely Dusting agents preferably containing of active substance can be manufactured therefrom by mixing with kaolin or Spraying Powder To manufacture a spraying the following for are mixed and finely 50 parts of an active substance according the present invention 20 parts highly adsorbent silica 25 parts of Bolus alba of sodium disulphonate and parts of a reaction product of octylphenol and ethylene Emulsion Concentrate Readily soluble active substances can also be formulated as ah emulsion concentrate in accordance with the following instructioni 20 parts of an active substance 70 parts of xylene 10 parts of a mixture of a reaction product of an alkylphenol with ethylene oxide and dodecylbenzenesulphonate are On dilution with water to the desired concentration a sprayable emulsion is Granules g of one of the active substances of the formula I are dissolved 100 ml of acetone and the acetone solution thus obtained is added to 92 g of granular attapulglte The whole is well mixed and the solvent stripped off in a rotary Granules containing of active substance are Example 3 The following varieties of plantswere sown in a Sinapis and The treatment of the indicated varieties of plants was carried out with a strength aqueous solution of the and days after in the leaf using an amount of 2 kg or 4 kg of active substance per The evaluation was 20 days after the treatment and the result shown in Tables I and II The treatment was carried out using the same but already 24 hours after Table Ratings plant unaffected or barely affected medium severe damage 9 plant dead Example Herbicidal Action The following types of plants were sown a Triticum Zea Chrysanthemum Brasaica The treatment of the indicated types of plants was carried out with a 1 strength aqueous solution of of the active substances days after in the leaf using an amount of 2 kg of active substance per The evaluation took place 20 days after the treatment and yielded the result shown in the table The treatment was carried out using the same but already hours after Compound 1 2 2 3 7 pre post pre post post pre Plants Triticum 1 2 1 1 1 1 2 Avena 2 2 1 Zea 2 2 2 2 1 2 2 1 Digitaria 9 8 9 9 Panicum 8 Poa 9 8 7 Alopecurus 6 8 8 Beta 9 9 9 9 Calendula 9 9 8 7 7 Chryanthemum 9 7 9 9 9 9 9 9 7 9 7 7 Brassica 9 9 9 7 7 9 9 9 7 7 Stellaria 9 9 9 9 9 9 9 9 9 9 plantsunaffected or affected medium damage severe damage 9 plant dead Example against Uromyces Bean plants in stage were sprayed with a suspension of active substance ormulated as a spraying until they were dripping wet aotive When the sprayed deposit had the plants were infested with a fresh spore suspension of bean rust and subsequently kept for day in a moist and then in a greenhouse at 20 The evaluation of experiment was based on the number of rust pustules present after 12 Untreated plants were used for cntrol purposes these plaris showed 100 attack at the end of the incubation the plants treated with the active substance the development of Uromyces appendiculates was totally Action against analogous test to but using the host plant and active active substance 6 led to total inhibitio of the development of Pucclnia insufficientOCRQuality

Claims (1)

1. CLAIMS Compounds of formula in which hydrogen or lower la a lower lower lower lower lower lower alkoxy or cycloalkyl or together with are form a to saturated heterocyclic and X ie oxygen or Compounds according to Claim of the general formula wherein is hydrogen or a group and a a alkoxy Compounds to Claim of the general formula wherein hydrogen or methyl and is or 27 methylpropen propynyl or Compounds according to of the general formula wherein a methyl or A process the manufacture of the compounds according to Claim aromatic compound of the formula in which H A is o or wherein or aryX and X is oxygen or is reacted with a primary or secondary amine of the formulae in which and have the same meaning as in Claim the two A and being capable of forming the urea A process for the manufacture of the compounds accordin to wherein the aniline of the formula 28 reacted with a compound of the formulae or or or wherein and have the same meaning as in is or aryl and is oxygen or Biocidal agents which contain as the active substance a compound of the formula in Claim by itself or together with a suitable carrier other agents according to Claim which contain as the carrier natural or regenerated mineral dispersing wetting binders or fertilisers and furthe cidal A method for combating phytopathogenic wherein an active substance according to Claim 1 or an agent according to Claim 7 or is applied to the plants which are to be protected from infestation by the A method for the selective control of weeds i cultures of cotton and corn wherein an active substance according to Claim 1 or an agent according to Claim 7 or is applied to the crops during the or stage the Applicants insufficientOCRQuality