DE3932534A1 - 1-Benzoyl-3-(4-cyano:benzyl) urea derivs. - for use as insecticides - Google Patents

Abstract

1-Benzoyl-3-(4-cyanobenzyl) urea derivs. of formula (I) are new. In (I), m, n each = 0-3; R1 = aryl or heteroaryl, both opt. substd., R2 = H, or opt. substd. alkyl, alkenyl, alkynyl or aralkyl, each R3 = halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio haloalkylthio, CN, alkoxycarbonyl, alkylsulphonyl or haloalkylsulphonyl, each R4 = halogen, CN, NO2, NH2, alkyl or dialkyl- amino, alkyl- or alkoxy- carbonylamino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylhtio, haloalkylthio, alkylsulphonyl or haloalkylsulphonyl, and X = O or S. More specifically, R1 = phenyl, naphthyl, furyl, thienyl, pyridyl or benzthiazolyl, opt. substd. by 1-3 of halogen, CN, NO2 or by alkyl, alkoxy, alkylthio, alkylsulphinyl, or alkylsulphonyl, all 1-4C and all opt. substd. by up to 9 halogen atoms; R2 = H, or 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 1-4C alkylphenyl or 1-4C alkylnaphthyl, all opt. substd. by F, Cl, or Br; and R3. R4 substits. are 1-3C, opt. with 1-5 halogen atoms. USE - (I) are active against pests of animals, partic. arthropods and nematodes, esp. insects and spiders, most esp. in agriculture, forestry, storage and material protection, also in the hygiene sector. They are active against sensitive or resistant species, and at all stages of development, partic. at the larval stage. (I) are excellent in wood and soil, also good alkali stability in lined soils.

Description

The invention relates to new substituted benzoyl urine Substance derivatives, processes for their preparation and their Use as a pesticide, in particular as insecticides.

It is already known that certain benzoylureas have insecticidal properties (cf. DE-A- 26 01 780).

Now the new substituted benzoyl urea Derivatives of the general formula (I)

in which
m and n independently of one another represent the numbers 0, 1, 2 or 3,
R¹ stands for optionally substituted aryl or heteroaryl,
R² stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl or aralkyl,
R³ represents identical or different radicals from the series halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cyano, alkoxycarbonyl, alkylsulfonyl or haloalkylsulfonyl,
R⁴ represents identical or different radicals from the series halogen, cyano, nitro, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkyl thio, haloalkylthio, alkylsufonyl and halogen alkylsulfonyl and
X represents oxygen or sulfur,
found.

It was also found that the new ones were substituted Benzoyl urea derivatives of the general formula (I) get when one

• (a) substituted anilines of the general formula (II) in which
  m, R¹, R² and R³ have the meanings given above,
  with benzoyliso (thio) cyanates of the general formula (III) in which
  n, R⁴ and X have the meanings given above,
  if appropriate in the presence of a diluent, or
• (b) substituted phenyliso (thio) cyanates of the general formula (IV) in which
  m, R¹, R², R³ and X have the meanings given above,
  with benzoic acid amides of the general formula (V) in which
  n and R⁴ have the meanings given above,
  if appropriate in the presence of a diluent.

The new compounds of general formula (I) gene about surprising, beneficial properties that their use as pesticides lichen; they show interesting arthropodicidal properties and are characterized by very star ke insecticidal efficacy.  

In the general formulas, halogen, fluorine, Chlorine, bromine or iodine, preferably fluorine, chlorine or Bromine.

m preferably stands for the numbers 0, 1 or 2, in particular especially for 1 or 2, the substituents being preferred in meta position (3 or 3.5 position) relative for urea NH grouping.

n is preferably the number 1, 2 or 3, in particular especially for 1 or 2, where the substituents are before preferably in the ortho position (2- or 2.6 position) rela tiv to the carbonyl group.

Optionally substituted groups can be one or several, preferably 1 to 5, in particular 1 to 3 and particularly preferably 1 or the same or different Bear substituents.

In the general formulas, alkyl means straight-chain or branched alkyl, preferably with 1 to 6, in particular especially with 1 to 3 carbon atoms. Be exemplary called: methyl, ethyl, propyl and isopropyl.

In alkyl-containing groups, such as alkoxy, alkylthio, Alkoxycarbonyl, alkylsufonyl, alkylamino, dialkylamino, Alkylcarbonylamino and alkoxycarbonylamino the alkyl radicals also preferably 1 to 6, in particular their 1 to 3 carbon atoms. Examples are ge named: methoxy, ethoxy, propoxy, isopropoxy, methylthio,  Ethylthio, propylthio, isopropylthio, methoxycarbonyl, Ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, Methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopro pylsulfonyl, methylamino, ethylamino, propylamino, iso propylamino, dimethylamino, diethylamino, acetylamino, Propionylamino, methoxycarbonylamino and ethoxycarbo nylamino.

In haloalkyl-containing groups, such as haloalkyl, Haloalkoxy, haloalkylthio and haloalkylsulfo nyl, the alkyl radicals also preferably contain 1 to 6, especially 1 to 3 carbon atoms and before preferably 1 to 9, in particular 1 to 5 halogen atoms.

Preferred halogen substituents are in the group fluorine, chlorine and / or bromine, especially fluorine and / or chlorine.

Examples include: fluoromethyl, chloromethyl, Difluoromethyl, dichloromethyl, chlorofluoromethyl, triflu ormethyl, trichloromethyl, fluorodichloromethyl, chlorodi fluoromethyl, trifluoroethyl, chloroethyl, chlorodifluor ethyl, tetrafluoroethyl, chlorotrifluoroethyl, difluorme thoxy, trifluoromethoxy, chlorodifluoromethoxy, trifluor ethoxy, chloroethoxy, chlorodifluoroethoxy, tetrafluoroetho xy, chlorotrifluoroethoxy, difluoromethylthio, trifluorme thylthio, chlorodifluoromethylthio, chloroethylthio, tri fluoroethylthio, chlorodifluoroethylthio, tetrafluoroethyl thio, chlorotrifluoroethylthio, difluoromethylsulfonyl, Trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, Te trafluoroethylsulfonyl and chlorotrifluoroethylsulfonyl.  

Alkenyl or alkynyl mean in the general formulas straight-chain or branched alkenyl or alkynyl, preferably with 2 to 6, in particular with 2 or 3 Carbon atoms.

Examples include: ethylene, propenyl, 1-methyl ethenyl, ethynyl and propynyl.

Aralkyl preferably means in the general formulas Phenylalkyl or naphthylalkyl with preferably 1 to 4, especially 1 or 2 carbon atoms in a straight chain or branched alkyl part.

Examples include: phenylmethyl, 1- or 2-Phe nylethyl and naphthylmethyl.

As preferred substituents for those mentioned for R² Groupings are alkyl, alkenyl, alkynyl and aralkyl Halogens, such as fluorine, chlorine and / or bromine, in particular Called fluorine and / or chlorine.

Aryl preferably means in the general formulas Phenyl or naphthyl, especially phenyl.

Heteroaryl means preferred in the general formulas wise a five- or six-membered, if necessary benzanellated heteroaromatic grouping with 1 to 3 heteroatoms, such as nitrogen, oxygen and / or Sulfur.

Examples include: furyl, thienyl, pyridyl and Benzthiazolyl.  

As preferred substituents of the aryl or heteroaryl Groupings may be mentioned: halogen, preferably fluorine, Chlorine and / or bromine, cyano, nitro, each straight chain or branched alkyl, haloalkyl, alkoxy, halogen alkoxy, alkylthio, haloalkylthio, alkylsulfinyl, Haloalkylsulfinyl, alkylsulfonyl and / or halogen alkylsulfonyl each having 1 to 4 carbon atoms and optionally 1 to 9, preferably 1 to 5, in particular 1 to 3 halogen atoms, preferably fluorine and / or Chlorine atoms.

In the general formulas, R1 is preferably Phenyl, which is represented by 1 or 2 identical or different Residues from the halogen series (preferably fluorine or Chlorine), alkyl, haloalkyl, alkoxy, haloalkoxy, Alkylthio and haloalkylthio each with 1 to 4 Carbon atoms (preferably chlorine, fluorine, methyl, Trifluoromethyl, trifluoromethoxy and trifluoromethylthio) is substituted.

In the general formulas, R² is preferably Hydrogen or alkyl with 1 to 4 carbon atoms (preferably for hydrogen).

In the general formulas, (R³) _{m is} preferably 2- or 2,5-halogen, in particular 2- or 2,5-chlorine.

In the general formulas, (R⁴) _m preferably represents 2- or 2,6-halogen, in particular 2-fluorine, 2-chlorine, 2,6-difluoro, 2,6-dichloro or 2-fluoro-6-chlorine.

In the general formulas, X is preferably Oxygen.

The preferred definitions set out here apply also for the preferred listed below Combinations of the definitions in a corresponding way.

Preferred are the new substituted benzoyl urea derivatives of the formula (I) in which
m represents the numbers 0, 1 or 2,
n represents the numbers 1, 2 or 3,
R¹ represents phenyl, naphthyl, furyl, thienyl, pyridyl or benzthiazolyl, where these groups can each be monosubstituted to trisubstituted, identically or differently, by halogen, preferably fluorine, chlorine or bromine, by cyano or nitro, by alkyl, haloalkyl, Alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, halogenalkylsulfinyl, alkylsulfonyl and haloalkyl sulfonyl each having 1 to 4 carbon atoms and optionally 1 to 9 halogen atoms,
R² represents hydrogen or radicals from the series alkyl having 1 to 6 carbon atoms, alkenyl and alkynyl each having 2 to 6 carbon atoms, phenylalkyl and naphthylalkyl each having 1 to 4 carbon atoms in the alkyl part, each substituted by fluorine, chlorine and / or bromine,
R³ represents fluorine, chlorine, bromine or alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonyl, alkylsulfonyl or haloalkylsufonyl, each having 1 to 3 carbon atoms in the alkyl components and optionally having 1 to 5 halogen atoms,
R⁴ for fluorine, chlorine, bromine, cyano, nitro, amino or for alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkyl sulfonyl or haloalkylsulfonyl each having 1 to 3 carbon atoms in the alkyl components and optionally 1 to 5 halogen atoms and
X represents oxygen or sulfur.

The new substituted benzoylurea derivatives of the formula (I) in which m represents the numbers 1 or 2 are particularly preferred,
n represents the numbers 1 or 2,
R¹ represents optionally single or double, identical or different phenyl substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromoxy, difluoromethylthio or trifluoromethylthio, or thienyl or pyridyl, these radicals optionally being single or double, identical or are differently substituted by fluorine, chlorine, bromine and / or methyl,
R² represents hydrogen, methyl, ethyl, propyl or isopropyl,
R³ represents fluorine, chlorine or methyl,
R⁴ represents fluorine or chlorine and
X stands for oxygen.

The for the compounds of general formula (I) given general and preferred residual definitions also apply to the connections of the other general Formulas (intermediate or preliminary products) accordingly.

Used for process variant (a), for example 3-chloro-4- (1-cyano-1- (4-fluorophenyl) -2-methyl- propyl) aniline and 2-chloro-6-fluoro-benzoyl isocyanate as Starting materials, the course of the reaction can be the following formula scheme is shown:  

Used for process variant (b), for example wise 3-fluoro-4- (1-cyano-1- (2-difluoromethoxy-phenyl) - propyl) phenyl isocyanate and 2-chloro-benzamide as Aus materials, the reaction can be carried out by the fol The following formula scheme can be reproduced:

The process variant (a) according to the invention for the preparation of compounds of formula (I) turning  Starting materials of the formula (II) are known and / or can be made by methods known per se (see DE-A 26 10 837 / US-PS 440 05 218, DE-A 38 34 272).

The process variant (a) according to the invention continue to be used.

Starting materials of the formula (III) are known and / or can be prepared by methods known per se are (cf. DE-OS 21 23 236, DE-OS 25 04 982, DE-OS 26 01 780, DE-OS 28 01 316, DE-OS 28 37 086, DE-OS 3 21 761, DE-OS 32 17 620).

The process variant (b) according to the invention Preparation of compounds of formula (I) as Aus Starting materials for the substituted phenyliso used (Thio) cyanates of the formula (IV) are obtained if one corresponding substituted anilines of the general Formula (II) in the usual way with phosgene or thio phosgene, optionally in the presence of a dilution means such. B. toluene, chlorobenzene, xylene or o- Dichlorobenzene, at temperatures between 0 ° C and 150 ° C implemented and the reaction product then under ver distilled under reduced pressure.  

To continue to be used in process variant (b) The starting materials of the formula (V) are known and / or can be produced by methods known per se (see literature on the starting materials of the Formula (III)).

As diluents come when performing the Process variants (a) and (b) practically all inert organic solvents in question. These include ins special aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, Cyclohexane, petroleum ether, petrol, ligroin, benzene, Toluene, xylene, methylene chloride, ethylene chloride, chloro form, carbon tetrachloride, chlorobenzene and o-dichlor benzene, ethers such as diethyl and dibutyl ether, glycol dime ethyl ether and diglycol dimethyl ether, tetrahydrofuran and Dioxane, ketone, such as acetone, methyl ethyl, methyl isopro pyl and methyl isobutyl ketone, esters such as acetic acid ethyl esters and ethyl esters, nitriles, such as. B. Acetoni tril and propionitrile, amides, such as. B. Dimethyl form amide, dimethylacetamide and N-methyl-pyrrolidone, and Tetramethylene sulfone.  

The reaction temperature in the process variants (a) and (b) varied within a wide range will. The procedure is generally carried out variant (a) between 20 ° C and 180 ° C, preferably between 40 ° C and 120 ° C and with the process variant (b) between 20 ° C and 200 ° C, preferably between 60 ° C and 190 ° C. The method var according to the invention antennas are generally carried out at normal pressure leads.

To carry out the process variants according to the invention the starting materials are usually approximately equimolar Amounts used. An excess of one or the other other reaction components bring no essential Advantages.

The reaction products are worked up after usual methods, e.g. B. by vacuuming the failed a product.

The compounds of the general formula (I) are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, and particularly preferably insects which occur in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector. They are active against normally sensitive and resistant species and against all or individual stages of development, in particular against insects in the larval stage. The pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Arma dillidium vulgare, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttula tus.
From the order of the Chilopoda z. B. Geophilus carpopha gus, Scutigera spec.
From the order of the Symphyla z. B. Scutigerella immacu lata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of the Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
From the order of the Dermaptera z. B. Forficula auricula ria.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.
From the order intermedius, Piesma quadrata, Cimex lectula rius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossy pii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoropaliphasum. Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Sais setia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossy piella, Bupalus piniarius, Cheimatobia brumata, Litho colletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorr hoea, Lymantria spp. Bucculatrix thurberiella, Phylloc nistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplocapsia n ., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Ca coecia podana, Capua reticulana, Choristoneura fumi ferana, Clysia ambiguella, Homona viranima.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acan thoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysoyzapharia, syllable, spp. Sitophilus spp., Otiorrhynchus sul catus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthre nus spp., Attagenus spp., Lyctus spp., Meligethes aene us, Ptinusium spp., Ptinusium spp psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.
From the order of the Hymenoptera z. B. Diprion spp., Hop locampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp-, Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucillia spp., Chrysomyia spp., Cuterebra spp., Gastophilus spp., Hyp pobosca spp., Stom spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Os cinella frit, Phorbia spp., Pegomyia hyoscyami, Cerati tis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheo pis, Ceratophyllus spp.
From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipice phalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psororioptes spp. , Sarcoptes spp., Tarso nemus spp., Bryobia praetiosa, Panonychus spp., Tetra nychus spp.

The compounds of the general formula according to the invention (I) are particularly characterized by very strong ones insecticidal effectiveness. They show in particular  against insect pests excellent effect, especially against caterpillars (e.g. Plutella maculipennis, Plutella xylostella, Heliothis virescens and Spodoptera frugiperda) and can therefore preferably be used as plant protection products be used.

The active ingredients can depend on their respective physical and / or chemical properties usual formulations are transferred, such as solutions, Emulsions, suspensions, powders, foams, pastes, gra nulates, aerosols, active ingredient-impregnated natural and syn synthetic materials, fine encapsulation in polymers Fabrics and in coating compositions for seeds, also in form burnings with fuel sets, such as smoking cartridges, cans, -spirals u. Ä., and ULV cold and warm fog formulation stanchions.

The formulations are produced in a known manner provides, e.g. B. by mixing the active ingredients with stretch agents, i.e. liquid solvents, are under pressure liquefied gases and / or solid carriers, optionally using surface ac tive agents, so emulsifiers and / or dispersants agents and / or foaming agents. In case of Use of water as an extender can e.g. Belly Use organic solvents as auxiliary solvents be det. Essentially come as liquid solvents in question: aromatics, such as xylene, toluene, or Al kylnaphthalenes, chlorinated aromatics or chlorinated ali  phatic hydrocarbons, such as chlorobenzenes, chlorine ethylene or methylene chloride, aliphatic coal water serstoffe, such as cyclohexane or paraffins, e.g. B. petroleum fractions, alcohols, such as butanols or glycol, and their ethers and esters, ketones, such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly po lare solvents such as dimethylformamide and dimethyl sulfoxide and water; with liquefied gaseous Extenders or carriers are such liquids ten meant, which at normal temperature and below Normal pressure are gaseous, e.g. B. aerosol propellants, such as Halogenated hydrocarbons as well as butane, propane, stick fabric and carbon dioxide; come as solid carriers in question: e.g. B. natural stone powder, such as kaolins, Clay, talc, chalk, quartz, attapulgite, Montmoril lonite or diatomaceous earth and synthetic rock powder, such as finely divided silica, aluminum oxide and silica Kate; come in as solid carriers for granules Question: e.g. B. broken and fractionated natural Ge stones like calcinite, marble, pumice, sepiolite, dolomite such as synthetic granules from inorganic and orga flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stem; as an emulsifier and / or foam-generating agent come into question: z. B. non-ionic and anionic emuls gators, such as polyoxyethylene fatty acid esters, polyoxy ethylene-fatty alcohol ether, e.g. B. alkylaryl polyglycol Ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and Protein hydrolyzates; as dispersants are: e.g. B. lignin sulfite and methyl cellulose.  

Adhesives such as carboxy can be used in the formulations methylcellusolse, natural and synthetic powdery, granular or latex-shaped polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. Iron oxide, titanium oxide, ferrocyan blue and organic color substances such as alizarin, azo and metal phthalocyanine color substances and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc are used the.

The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90%.

The active ingredients can be in their commercially available form as well as in those prepared from these formulations Application forms in a mixture with other active ingredients, such as insecticides, attractants, sterilants, acaricides, Nematicides, fungicides, growth regulators or herbicides. Insecticides include for example phosphoric acid esters, carbamates, carbon acid esters, chlorinated hydrocarbons, phenyl urine substances, substances produced by microorganisms u. a.  

The active ingredients can also be in their commercially available Formulations as well as in from these formulations prepared application forms in mixture with synergists are available. Synergists are connections through which the Effect of the active ingredients is increased without the synergist must be actively active itself.

The active ingredient content of the from the commercial formu Formulations prepared use can be widely used range vary. The drug concentration of the users Forms of application can be from 0.0000001 to 95% by weight of active ingredient substance, preferably between 0.0001 and 1 wt .-% lie gene.

The application takes place in one of the application forms adapted usual way.

When used against hygiene and storage pests the active ingredients are characterized by an excellent Residual effect on wood and clay as well as by a good Alkali stability on limed substrates.

Manufacturing examples Example 1

(Method (a))

A mixture of 31.5 g (0.10 mol) of 3,5-dichloro-4- (4- chloro-α-cyano-benzyl) aniline, 15.5 g (0.10 mol) 2,6-di fluorobenzoyl isocyanate and 150 ml of toluene is 60 minutes heated to boiling under reflux. After cooling down 20 ° C, the crystalline product is obtained from Ab suck isolated.

41.6 g (82% of theory) of 1- (2,6-difluoro-ben are obtained zoyl) -3- (3,5-dichloro-4- (4-chloro-α-cyano-benzyl) phenyl) - urea with a melting point of 220 ° C.

Analogously to Example 1 and in accordance with the general Be Description of the process variant (a) according to the invention and (b) can be, for example, those in the following Compounds of formula (I) listed in Table 1 be put.  

Table 1

Examples of the compounds of the formula (I)

Example A Heliothis test

Solvent: 3 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent and the specified amount of emul gator and dilutes the concentrate with emulsifier Water to the desired concentrations.

Soybean plants (Glycine soja) are effective processing of the desired concentration delt. In ten repetitions, one sheet of the treated plant placed in a plastic box and with one larva (L₂) each of the cotton capsule worm (Heliothis virescens). After 3 days you feed each can another leaf of the corresponding plant. On the 7th day, the larvae are put on untreated artificial food ter implemented.

After the desired time, the kill in% Right. 100% means that all animals are killed were; 0% means that no animals have been killed.

In this test, e.g. B. the connections of Her Position examples (1) and (3) in an exemplary Concentration of 0.00016% after 14 days a 100% Killing.  

Example B Plutella test

Solvent: 3 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation mix 1 part by weight of active ingredient with the specified amount of solvent and the specified amount of emul gator and dilutes the concentrate with emulsifier Water to the desired concentrations.

Cabbages (Brassica oleracea) are used with the active preparation of the desired concentration delt. A leaf of the treated plant is placed in a Plastic box placed and with larvae (L₂) the cockroach (Plutella xylostella). After 2 and 4 days one more leaf from the same plant for each Refill used.

After the desired time, the kill in% Right. 100% means that all animals are killed were; 0% means that no animals have been killed.

In this test, e.g. B. the connections of Her position examples (1), (3) and (4) in one example adhere to a concentration of 0.0008% after 14 days 100% kill.  

Example C Spodoptera test

Solvent: 3 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

For the preparation of a suitable active ingredient preparation mix 1 part by weight of active ingredient with the specified amount of solvent and the specified amount of emul gator and dilutes the concentrate with emulsifier Water to the desired concentrations.

Soybean plants (Glycine soja) are effective preparation of the desired concentration delt. In ten repetitions, one sheet of the treated plant placed in a plastic box and with one larva (L₂) each of the army worm (Spodoptera frugiperda) occupied. After 3 days, you feed one per can another leaf of the corresponding plant. On the 7th Day the larvae are switched to untreated synthetic feed set.

After the desired time, the kill in% Right. 100% means that all animals are killed were; 0% means that no animals have been killed.

In this test, e.g. B. the connection of the Her Position examples (1) and (3) in an exemplary Concentration of 0.00016% after 14 days a 100% Killing.

Claims (10)

1. Benzoyl urea derivatives of the general formula (I) in which
m and n independently of one another represent the numbers 0, 1, 2 or 3,
R¹ stands for optionally substituted aryl or heteroaryl,
R² stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl or aralkyl,
R³ represents identical or different radicals from the series halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cyano, alkoxycarbonyl, alkylsulfonyl or haloalkylsulfonyl,
R⁴ represents identical or different radicals from the series halogen, cyano, nitro, amino, alkyl amino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl and haloalkyl sulfonyl and
X represents oxygen or sulfur. 2. Benzoyl urea derivatives of the formula (I) according to Claim 1, in which
m represents the numbers 0, 1 or 2,
n represents the numbers 1, 2 or 3,
R¹ stands for phenyl, naphthyl, furyl, thienyl, pyridyl or benzthiazolyl, where these groups can each be monosubstituted to trisubstituted, identically or differently, by halogen by cyano or nitro, by alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl each having 1 to 4 carbon atoms and optionally 1 to 9 halogen atoms,
R² stands for hydrogen or for fluorine, chlorine and / or bromine-substituted radicals from the series alkyl with 1 to 6 carbon atoms, alkenyl and alkynyl each with 2 to 6 carbon atoms, phenylalkyl and naphthyl alkyl each with 1 to 4 carbon atoms in the alkyl part
R³ represents fluorine, chlorine, bromine or alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxycarbonyl, alkylsulfonyl or haloalkylsulfonyl each having 1 to 3 carbon atoms in the alkyl component and optionally having 1 to 5 halogen atoms,
R⁴ for fluorine, chlorine, bromine, cyano, nitro, amino or for alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkyl, halo genalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl or halogen alkylsulfonyl each having 1 to 3 carbon atoms in each Alkyl components and optionally 1 to 5 halogen atoms and
X represents oxygen or sulfur. 3. Benzoyl urea derivatives of the formula (I), according to claim 1 in which
m represents the numbers 1 or 2,
n represents the numbers 1 or 2,
R¹ represents phenyl optionally substituted once or twice, identically or differently by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, di fluoromethoxy, trifluoromethoxy, difluoromethylthio or trifluoromethylthio, or thienyl or pyridyl, these radicals optionally being single or duplicate, the same or are differently substituted by fluorine, chlorine, bromine and / or methyl,
R² represents hydrogen, methyl, ethyl, propyl or isopropyl,
R³ represents fluorine, chlorine or methyl,
R⁴ represents fluorine or chlorine and
X stands for oxygen. 4. benzoyl urea derivatives of the formula (I) according to claim 1, in which (R⁴) _{n represents} 2- or 2,6-halogen. 5. Benzoyl urea derivatives of the formulas 6. Process for the preparation of the benzoylurea derivatives of the general formula (I) in which
m and n independently of one another represent the numbers 0, 1, 2 or 3,
R¹ stands for optionally substituted aryl or heteroaryl,
R² stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl or aralkyl,
R³ represents identical or different radicals from the series halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cyano, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl,
R⁴ represents identical or different radicals from the series halogen, cyano, nitro, amino, alkyl amino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl and haloalkyl sulfonyl and
X represents oxygen or sulfur,
characterized in that one

• (a) substituted anilines of the general formula (II) in which
  m, R¹, R² and R³ have the meanings given above,
  with benzoyliso (thio) cyanates of the general formula (III) in which
  n, R⁴ and X have the meanings given above,
  if appropriate in the presence of a diluent, or
• (b) substituted phenyl (thio) cyanates of the general formula (IV) in which
  m, R¹, R², R³ and X have the meanings given above,
  with benzoic acid amides of the general formula (V) in which
  n and R⁴ have the meanings given above,
  optionally in the presence of a diluent.

7. Pest control, characterized by contains at least one compound of Formula (I) according to claims 1 or 6. 8. Use of compounds of formula (I) according to claims 1 or 6 for combating pests succeed. 9. Method of combating pests, thereby characterized in that compounds of the formula (I) according to claims 1 or 6 on pests and / or their living space. 10. Process for the preparation of pesticides, characterized in that one Compounds of formula (I) according to claims 1 or 6 with extenders and / or surfaces active funds mixed.