JPS59176244A - Benzoylurea - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel substituted 1-phenyl-3-benzoyl-
(Thio)ureas, some processes for their preparation, and their use as pest control agents, in particular insecticides and acaricides.

It is known that certain benzoylureas have insecticidal properties. (See for example European Patent 0,057,888).

Formula (1) where X represents oxygen or sulfur, R1 represents hydrogen, halogen, nitro, alkyl or alkylthio, and R2, R4 and R5 are the same or different and represent hydrogen or halogen. , R3 represents 1 hydrogen, halogen or nitro, R6 or R7 are the same or different and represent hydrogen, halogen or alkyl, R8 and R9 are the same or different and represent hydrogen or halogen) and R10 represents halogenoalkylthio or halogenoalkoxy, and (1) if X represents oxygen, and R2, R3, R
4, R6, R8 and R9 represent hydrogen and R7 represents hydrogen or halogen, and (a) R1 and R5 both represent hydrogen, or (b) R1 is halogen, nitro or alkyl. and if R5 represents hydrogen, in these cases the radical R10 always refers to halogenoalkylthio, and (2) if X represents oxygen or sulfur and R6 represents chlorine, and R8 represents hydrogen or chlorine, R9 represents hydrogen, and R10 represents halogenoalkylthio or halogenoalkoxy, and (a) R1 and RB represent halogen, and R2,
R4 and R5 represent hydrogen, or (b) R5 and R
3 represents halogen and R1, R2 and R4 represent hydrogen, or (c) R1 and R4 represent halogen and R2, R3 and R5 represent hydrogen;
or (d) R2 and R5 represent halogen, and R1,
If R3 and R' represent hydrogen, in these cases the group R7 always represents hydrogen or alkyl, the novel substituted 1-phenyl-3-benzoyl-(thio)
Urea has been discovered - these new compounds have strong exobiological properties, especially insecticidal properties, making it possible to use the same compounds as pest control agents, especially insecticides and acaricides. .

Furthermore, the novel substituted 1-phenyl-5-benzoyl-(thio)ureas of formula (I) are characterized by: a) formula (■) in which R6, R7, R8, R9 and R10 have the meanings given above; A substituted aniline of the formula (■) in which X, R1, R2, R3, R4 and R5 have the meanings given above, and a benzoyl-iso(thio)cyanate of the formula (■) and, if appropriate, a diluent. or b) a substituted phenyl-yne(thio)cyanate of formula (■) in which X, R6, R7, R8, R9 and R10 have the meanings given above, ■) in the presence of a benzoic acid amide and, if appropriate, a catalyst, in which R1, R2, R3, R4 and R5 have the meanings given above;
It has been found that this can be obtained, if appropriate, by a method of reaction in the presence of a diluent.

The alkyl groups R1, R6 and R7 and the alkylthio group R1 are straight-chain or branched, having in the alkyl part 1 to 12, preferably 1 to 6, particularly preferably 1 to 4 carbon atoms. Contains alkyl. For example, methyl, ethyl, n-propyl, 1-propyl, n-butyl, i-
butyl, sec-butyl, tert, -butyl-methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, see, -butylthio, and tert. -Butylthio can be mentioned.

R of halogenoalkylthio group and halogenoalkoxy group
10 has 1 to 6, preferably 1 to 4, particularly preferably 1 or 2 carbon atoms in its alkyl moiety, and preferably 1 to 6, particularly preferably 1 to 2 carbon atoms. 4
straight-chain or branched alkyl, identical or different, preferably having halogen atoms selected from fluorine, chlorine or bromine, particularly preferably fluorine atoms. For example, trifluoromethylthio, chlorodifluoromethylthio, trifluoroethylthio, chlorotrifluoroethylthio, tetrafluoroethylthio, trifluoromethoxy,
Mention may be made of difluoromethoxy, tetrafluoroethoxy, chlorotrifluoroethoxy and bromotrifluoroethoxy.

Unless otherwise specified, halogen refers to fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.

X preferably represents oxygen.

The new compound of formula (1) has properties that allow it to be used as a pest control agent. In particular, these new compounds exhibit excellent activity as insecticides and acaricides not found in other compounds.

The present invention preferably provides compounds of the formula (I) in which X represents sulfur or oxygen and R1 is hydrogen, halogen, nitro or from the series of groups consisting of C1-C5-alkyl and C1-C6-alkylthio. R2, R4 and R5 are the same or different and represent hydrogen or halogen; R3 represents hydrogen, halogeno or nitro; R6 and R7 are the same or different; , and represents hydrogen, halogen or a C1-C6 group, R8 and R9 are the same or different and represent hydrogen or halogen, and R10 has 1 to 4 carbon atoms and 1 to 4 halogen atoms. (1) if X represents oxygen and R2, R3, R
4, R6, R8 and R9 represent hydrogen and R7 represents hydrogen or halogen, and (a) both R1 and R5 represent halogen, or (b) R1 is halogen, nitro, or represents C6 alkyl and R5 represents hydrogen, in these cases the radical R10 always represents C1-C4-halogenoalkylthio, and (2) if 1X represents oxygen or sulfur and Ro represents chlorine and R11 represents hydrogen or chlorine, R9 represents hydrogen, and R10 represents C1-C4-halogenoalkylthio or C1
~C4-halogenoalkoxy, and (a) R1 and R3 represent halogen, and R2,
R4 and R1+ represent hydrogen, or (b) R5 and R1 represent halogen and R1, R2 and R4 represent hydrogen, or (c) R1 and R4 represent halogen and R2, R3 and Does R5 represent hydrogen?
or (a) R2 and R5 represent halogen, and R
2, R3 and R4 represent hydrogen, the radical R7 in these cases represents hydrogen or C1-C6-alkyl.

In each case, halogens are fluorine, chlorine, bromine,
and/or iodine, preferably fluorine, monochlorine and/or bromine.

Particularly preferred compounds are of the formula (I) where X represents oxygen or sulfur, and R1 is hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i −
butyl, sec, -butyl, tert. -butyl, methylthio, ethylthio, n-propylthio to 1-propylthio, n-butylthio, 1-butylthio, sec, -butylthio, or tert. -butylthio, R2, R4 and R5 are the same or different and hydrogen, fluorine, chlorine or bromine, R3 represents hydrogen, fluorine, chlorine, bromine or nitro, R6 and R7 are the same or different, and hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-propyl, n-butyl, 1-butyl, sec. -butyl or tert. -butyl, R6 and R9 are the same or different and represent hydrogen, fluorine, chlorine or bromine, and B10 represents trifluoromethylthio or trifluoromethoxy, and (1), and X represents oxygen; and R2, R3, R4, R5, R6 and R9 represent hydrogen, and R7 represents hydrogen, fluorine, chlorine or bromine, and (a) R1 and R5 both represent fluorine, chlorine and/or bromine. or (b) R1 represents fluorine, chlorine, bromine, nitro or an alkyl group as mentioned above and R5 represents hydrogen, in these cases the radical R10 always represents trifluoromethylthio. and (2) if X represents oxygen or sulfur, and R6 represents chlorine, and R8 represents hydrogen or chlorine, and R9 represents hydrogen, and R10 represents trifluoromethylthio or trifluoromethoxy and (a) R1 and R3 represent fluorine, chlorine or bromine and R2, R4 and R5 represent hydrogen, or (b) R5 and R3 represent fluorine, chlorine or bromine) and R1, R2 and R4 represent hydrogen, or (c) R1 and R4 represent fluorine, chlorine or bromine and R2, R3 and R5 represent hydrogen, or (d) R2 and R5 represent fluorine, represents chlorine or bromine,
And if R1, R3 and R4 represent hydrogen, then in these cases the radical R7 is always hydrogen or a compound of the above-mentioned alkyl group.

Very particularly preferred compounds are of the formula (1) in which X represents oxygen, R1 represents hydrogen, fluorine, chlorine-bromine, nitro, methyl or methylthio, and R2, R4 and R5 represent hydrogen, fluorine , represents chlorine or bromine, R1 represents hydrogen, fluorine, chlorine or nitro - R6 and R7 are the same or different and represent hydrogen, chlorine or methyl, R8 and R9 are the same or different, and hydrogen to fluorine or chlorine, and R10 represents trifluoromethylthio or trifluoromethoxy, and (1) if R2, R3, R4, R6, R8 and R9 represent hydrogen, and R7 1 hydrogen or chlorine, and (a) both R1 and R5 represent fluorine, chlorine and/or bromine;
or (b) if R1 represents fluorine, chlorine, bromine, nitro or methyl and R5 represents hydrogen, in these cases the radical R10 always represents trifluoromethylthio, and (2) or , R6 represents chlorine, and R8 represents ~hydrogen or chlorine, and R9 represents hydrogen, and R10 represents trifluoromethylthio or trifluoromethoxy, and (a) R'' and R3 represent fluorine , chlorine and/or bromine and R2, R4 and R5 represent hydrogen) or (b) R5 and R3 represent fluorine, chlorine and/or bromine and R1, R2 and R4 represent hydrogen or (c) R1 and R4 represent fluorine, chlorine and/or bromine and R2, R3 and R5 represent hydrogen, or (d) R2 and R5 represent fluorine, chlorine and/or or bromine, and if R1, R3 and R4 represent hydrogen, then in these cases the radical R7 is a compound of the following, in which case R7 represents hydrogen or methyl.

If, 4-(2-chloro-4-trifluoromethoxy-
If phenoxy)-3-methylaniline and 2,6-cyfluoropenzoyl isocyanate are used as starting materials for process (a), the reaction route can be represented by the formula below.

If, 4-(2-chloro-4-trifluoromethoxy-
If phenoxy)-6-methylphenyl thiocyanate and 2,6-cyfluoropenzamide are used as starting materials for process (b), the reaction route can be represented by the formula below.

Examples of the compound of formula (■) include the following compounds.

The substituted aniline of formula (■) used as starting material is
are known and/or can be produced by processes and methods known from the literature (DE-OS (German Published Patent Application) No. 5.217.619, DE-OS (
German published patent) specification, No. 3, 217, 620,
and European Patent No. 0,057,588). The amine groups can be converted into isocyanate or inthiocyanate groups by conventional methods, for example by reaction with phosgene or thiophosgene. The corresponding substituted phenyliso(thio)cyanates of formula 9 (■) are thereby obtained.

The corresponding isocyanates or isothiocyanates of the substituted anilines of formula (■) listed in Table 1 can be mentioned as examples of compounds of formula (■).

Examples of the compound of formula (■) include the following compounds: 2-fluoro-, 2-chloro-, 2-bromo-, 2-
Nitro-12-methyl-12-methylthio-12,6-
difluoro-, 2,6-dichloro-12-chloro-6-
Fluoro-, 2-chloro-4-nitro-, 3,4-difluoro-13,4-dichloro-, 2,3,6-trichloro-, 4-fluoro-, 4-chloro-, 4-bromo-,
and 4-nitrobenzoyl incyanate or -benzoyl inthiocyanate.

The starting materials of formula (■) are known.

Examples of the compound of formula (■) include the following compounds: 2-fluoro-, 2-chloro-, 2-bromo-, 2-nitro-, 2-methyl-, 2-methylthio-, 2,6-difluoro- -, 2,6-dichloro-, 2-chloro-6-fluoro-, 2-chloro-4-nitro-, 3,4-difluoro-, 3,4-dichloro-, 2,3,6-trichloro-, Mention may be made of 4-fluoro-, 4-chloro-, 4-bromo- and 4-nitrobenzoic acid amides.

Compounds of formula (V) are known. Almost all inert organic solvents are suitable as diluents. Among these, in particular) aliphatic and aromatic optionally halogenated hydrocarbons, such as pentane,
hexane, heptane, cyclohexane, petroleum ether,
benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and diptyle ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and sooxane,
Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitrites such as acetonitrile and gallobionitrile-amides such as dimethylacetamide and N-methyl Examples include pyrrolidone and tetoshimetersulfone.

The catalyst used in the reaction of method (b) is preferably a tertiary catalyst.
amines such as triethylamine, and 1,4-diazabicyclo[2,2,2]octane, and organotin compounds such as dibutyltin dilaurate.

The reaction temperature can be varied within a relatively wide range. Generally, method (a) is carried out at 20-180°C, preferably at 4°C.
carried out at 0-120°C, method (b)
It is preferably carried out at 60-190°C.

The method of the invention is generally carried out under atmospheric pressure.

In carrying out the process of the invention, the starting materials are usually used in approximately equimolar amounts. There is no practical benefit to having an excess of one or the other of the reactants.

The reaction products are treated by means of electrical current application, for example by suction filtration of the precipitated product or by extraction of undesired by-products from the reaction mixture. The product is identified by its melting point.

The active compound is highly resistant to plants, has a desirable low toxicity to warm-blooded animals, and is suitable for use in agriculture, forestry, etc.
protection of stored products and materials and pests in the sanitary field;
Particularly suitable for controlling insects and mites. The active compounds are effective against the above-mentioned pests, both on sensitive and resistant species and on all or some of their growth stages. , including those of the order Isopoda, such as Oniscus asellus, Armandillidium vulga
re), and Borsselio scaca (porcell).
io scabar); diplopoda (D iplopoda)
), for example, those of Braniurus cutulatus (B
laniulus guttula-tus): of the order Chilopoda, e.g.
Geophilus carbophagus
arpophagus) and Scutig
eraspp. ); those of the order Symphyla, such as Scutigerel immaculata
aimmaculata); those of the order Thysanula, such as Lepisma Saccharin
a); Collembola, such as Onychiurus
s arma-tus); those of the order Ortloptera, such as Blatta orientalis;
alis), American cockroach (Periplaneta)
americana), Leucophae maderae (L
eucophaea maderae), German cockroach (Blattella germanica),
Acheta domesticus
icus), mole (Gryllotalpa spp.
), Locusta migrato
ria migratorioides), Melanoplus dif.
ferentialis) and Schistocerca gregaria.
: Those of the order Dermaptera, such as Forficula auricularia.
lauricularia;; of the order Isoptera, such as Reticulitermes sp.
p. ); members of the order Anoplura, such as Phylloxera bastarix
vastat-rix), penfigus (pemph)
igus spp. ) and human lice (Pedicu
lus humanus corporis);
pp, ): Mallophaga
), such as Trichode
ctes spp. ) and Damalinea
nea spp. ) ; Thripidae
tera), such as He.
rcinothrips fetn-oralis)
and Thrips tabaci
; Heteroptera, such as Eurygaster spp.;
Dysdercus intermezzius (Dysdercus)
interme-dius), Piesma quad-rata, bed bug (Cimex lectularius), Rhodnius prolixus
and Triatoma spp.; those of the Homoptera, such as Aleurodes brassi
cae), cotton whitefly (Bem1sia taba)
ci), Trialeurodes bavolariorum (Tri
aleurodes vaporariorum), cotton aphid (Aphisgo-ssypii), radish aphid (B reviocorynebras)
sicae), Cry-pt.
omysus ribis), Doralis fabae (D
or-alis fabae), Doralis pomi (Do
ralis pomi), apple boll beetle (Erios
oma lanigerum), peach aphid (Hyalopterus arundinis), and wheat aphid (tvlacrosiphum).
avenaa), Myzus spp.
．． ), Phorodon hu
muli), wheat fin aphid (Rhopalos
iphum padi), Himeyokohai (Empoas)
ca spp. ), Eusceris virochatus (Eus
celis bilobatus), black leafhopper (Nephotettix cincticeps),
Lecanium corn
i), Olive scale insect (Saissetia)
oleae), Laodelpha
x Striatellus), brown planthopper (Ni
Laparvata lugens), Aonidiella auranNi, Aspidiotus hede
rae), Pseudococcus
us spp. ) and woodlice (Psilla sp.
p. ); Lepidoptera, such as Pectinophora gossy
piella), Bupal pinialius (Bupal)
us piniarius), Cheimatobia br-umata, and Lithocolletis blancaldera.
s blancardella), Hyponomeuta padella, diamondback moth (Plutella maculipennis)
, Malacosoma neustri
a), Euproctis chr.
Lyman-tr
ia spp. ), Bucculatrix thurberiella
), Phyllocnistis
citrella), Yaga (Agrotis spp.
), Euxoaspp., Feltia (
Feltia spp. ), Aerias Insulana (
Earias insulana), Heliothis (He
liothis spp. ), Hiroichi Mojoto (L
aphygma exigua), armyworm (Mam)
es-tra brassicae), pan-olis flammea, Prodenialitura, Spodoptera spp., Trichoplusia ni, Carbocapsa bomo Nella (Carpocapsa pomone)
lla), Pieris spp., Chilo spp., Corn borer (Pieris spp.), Pieris spp.
Pyraustanabilis), Ephes-tia kuehniella
), honey hemlock (Galleria me-llon)
ella), Teineola hiseriella (T 1neol)
abisselliella), T 1neapellionella, Hofmannophila bushtospletella
la pseudospretella), Cacoecia podana, Capua reticulana,
Christoneura fumihuelana (Choristone)
ura fu-miferana), Clysia ambiguella, Homona magnanima, and Tortrixviridan.
a); Coleoptera, such as Anobium puncta;
tum), Rhizoper
tha dominica), Bruchidiusobtectus, and French bean weevil (Acantho-scelides).
obtectus), Hylotorbes bajurus (H
ylotrupes bajulus), Agelastica alni, Leptinotarsa tesemlineata
deoemlrneata), Phaedon cochlea-riae,
Diabrotica spp., Psylliodesc
hrysocephala), Epilachna varivestis, Atomaria spp., Oryzaephilus suriname
nsis), Anthonomus s
pp. ), Sit-ophilus s
pp. ), Otiorrhynchis sulcaras (Otiorr
hychus sulcatus), Cosmopolites soridus, Ceuthorrhyn
cbus assimilis), Hibera postica (
Hypera postica), cuttlefish beetle (D
ermestes spp. ), Trogoderma (Tro
goderma spp. ), Anthrenus (Ant-
hrenus spp. ), Atagenus
nus Spp. ), Lyctus
spp. ), Meligtes Aeneus (Melige)
thes aeneus), the white beetle (Ptin
us 3pρ, ), Nibulus holeucas (Nipt
us hololeucus), Gibbium psylloides, Tribolium spp., Tenebrio molit
or), click beetles (Agriotes spp.)
, Con-oderus spp.,
Melolontha melolontha (Melolontha me)
lolontha), Amphimallon solstitialis
s) and Costeritra zealansica (Costel
Hymenoptera, such as Diprion spp., Hoplocampa spp., La.
siuspp. ), Monomori
um pharaonis) and wasps (Ves
pa spp. ); of the order Diptera;
For example, Aedes spp., Anopheles spp., Culex mosquito
x spp,), Drosophila melanogaster (Droso melanogaster)
phia melanogaster), house fly (M
usca spp. ), Fan-nia
spp. ), black fly Erimerocephala (Call
iphoro erythrocephala), Lucilia spp., Lucilia spp.
hrysomyaspp. ), Cuterebra (Cuter
ella spp. ), Gastroph
illus spp. ), Hyppobo
sca spp. ), Stomo-xys
spp. ), sheep fly (Oestrus spp.)
, Hypoderma spp., Horseflies (Hypoderma spp.)
Tabanus spp. ), Tannia s
pp. ), Bibio hortulanus
), Oscinella frito
T), Phormia spp., Pegomyahyoscyami
), Ceratitis cavitata
capitata), fruit fly Dacus oleae (Dacus o
leaae) and Gakanho Pardosa (Tipula
paludosa); Siphonapte
ra), such as the Xenopus flea (Xeno
psilla cheopis) and Ce
ratopyllus spp. ) ; Arachnida (Arac
hnida), such as Scorpio mauscis (
Scorpio maurus) and Latrodectus mac-ta
ns); those of the order Acarina, such as Acarus siro, Arg.
asspp. ), Kazuki Tani (Ornithodoro)
s spp. ), red mite (Dermanyssus g
allinae), Eliofinis Riches (Erio
phyes ribis), Citrus sabitani (Phyl.
Locoptruta oleivora), Boophilus spp., Rhi-picephalus spp., Amblyommaspp., Boophilus spp.
Hyalomma spp. ), Ixodes
spp. ), Psoropt
es spp. ), Cborio
ptes spp. ), Sarco-pt.
es spp. ), dust mite (Tarsonemus
spp. ), Bryobia pr
aetiosa), citrus apple spider mite (Panony
chus spp. ) and two-spotted spider mite (Tetran
ychus spp. ).

The active compounds may be present in the usual formulations, formulations, etc.
n), for example in solutions, emulsions, suspensions, powders, foams, liniments, granules, aerosols, natural or synthetic materials impregnated with active compounds, polymeric substances and in compositions for seed coating. It can be converted into dosage forms for use with micro-capsules and fumigation equipment, such as fumigation cartridges, fumigation cans, fumigation coils, etc., as well as into formulations for ULV room temperature and high temperature mist (concentrated liquid spraying).

These dosage forms can be prepared in a known manner, for example by combining the active compounds with fillers, i.e. liquid solvents, pressurized liquefied gases, and/or solid carriers, and optionally with surfactants, i.e. emulsifiers and/or foaming agents. It is also produced by mixing. When water is used as a bulking agent, organic solvents can also be used as co-solvents. The main ones suitable as liquid solvents are:
aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons,
For example chlorobenzene, chloroethylene, methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl Isobutyl ketone, or cyclohexanone, highly polarizable solvents such as dimethylformamide and dimethyl sulfoxide, and water. The liquefied gas extender or carrier is a liquid that is a gas at normal temperature and pressure, and includes, for example, an aerosol propellant, such as halogenated hydrocarbons, butane, propane, nitrogen, and carbon dioxide gas.

Suitable solid carriers include, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or gravel,
and ground synthetic minerals, such as dispersed silicic acid, alumina, and silicates; suitable as solid carriers for granules include, for example, ground and classified rocks, such as limestone, pumice, sepiolite and There are synthetic granules of dolomite and inorganic and organic ground grains, and granules of organic matter, such as sawdust, coconut husks, corn cobs and tobacco stalks.

Suitable emulsifiers and/or foaming agents include nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfones. These include acid salts, alkyl sulfate salts, aryl sulfonate salts, and albumin hydrolysis products.

Suitable dispersants include, for example, lignin-sulphite repellents and methylcellulose.

Adhesives, such as carboxymethyl cellulose, and natural or synthetic polymers in the form of powders, granules or latexes, such as gum ajibia, polyvinyl alcohol and polyvinyl acetic acid, can be used in the dosage form.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue and organic dyes such as alizarin dyes, azo dyes, metal phthalocyanine dyes, and micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc. It is possible to use salts of:

The dosage forms generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90%.

The active compounds according to the invention, in their commercially available dosage forms and in the application forms prepared from these dosage forms, may contain other active compounds, such as insecticides, baits, disinfectants, acaricides,
It can be present as a mixture with nematicides, fungicides, growth regulators or herbicides. Pesticides include, for example, phosphate esters, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, and substances produced by microorganisms.

The active compounds of the invention can furthermore be present in their commercially available dosage forms and in the application forms prepared from these dosage forms as a mixture with synergists. A synergist is a compound that increases the activity of an active compound, although it does not need to be active itself.

The active compound content of the application forms prepared from commercially available dosage forms can be varied over a wide range. The active compound count of the application form is 0.00000
01-95% by weight, preferably 0.0001-1% by weight
It is possible to be.

The compounds are used in the customary manner appropriate to the application form.

When used against sanitary pests and stored product pests, the active compounds show an outstanding residual effect on wood and clay and, in addition, excellent stability against alkalis on limestones. Show your gender.

The active compounds according to the invention are also suitable in the field of veterinary medicine for the control of external and internal parasites, such as by controlling harmful bodies such as increasing milk production, increasing animal weight, etc.
Good results such as improved skin tone and longer lifespan can be obtained.

The active compounds of the invention can be processed by methods known in the art.
For example, for outdoor use, e.g. in the form of dipping, spraying, irrigation, spot treatment and dusting, and for oral administration, e.g. through feed or drinking water, e.g. in the form of tablets, capsules, livestock drinks, and granules. .

The following Preparation Examples describe methods for making compounds of the invention.

Example 1 (Method a) 3.66 g (0.02 mol) of 2,6-cyfluoropenzoyl isocyanate are dissolved in 10 ml of toluene,
6.76 g (0.02 mol) of 3,5-dichloro-4-
(4-1 fluoromethoxyphenogysi)aniline 6
Add to 0 ml of dry toluene solution at 60°C. The mixture is then stirred for 1 hour at 80°C. After it has cooled to 20° C., the product is filtered with suction and dried.

9 g (86.5% of theory) of 1-(2,6-cyfluorobenzoyl)-3-[3,5-dichloro-4-(4-
Trifluoromethoxy-phenoxy)-phenyl]-urea (melting point: 194° C.) is obtained.

Example 2 (Method b) 2.42 g (0.01 mol) of 2-bromobenzoyl isothiocyanate is dissolved in 101 g of toluene and mixed with 3.32 g (0.01 mol) of 3,5-dimethyl -4
Add to a 50 ml dry toluene solution of -(3-chloro-4-trifluoromethoxyphenoxy)aniline at 60<0>C. The mixture is further stirred at 80° C. for 30 minutes. It is then evaporated and concentrated to about 20 ml. The precipitate is filtered off with suction and dried.

5.1 g (89% of theory) of 1-(2-bromobenzoyl)-3-[3,5-dimethyl-4-(3-chloro-
4-Trifluoromethoxyphenoxy)phenyl]urea (melting point: 167°C) is obtained.

The compound of formula (1) shown below was prepared similarly to Example 1 or 2 or method (a) or (b).

The following examples illustrate the biological activity of compounds of the invention.

Example A Plutella Test Solvent: 15 parts by weight dimethylformamide Emulsifier: 1 part by weight alkylaryl polyglycol ether To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is added to the above amount. The resulting stock solution is diluted with water to the desired concentration.

Cabbage (Brassica oleracea) leaves are soaked in a preparation of the desired concentration of active compound and diamondback moth (Plutella maculipennis)
caterpillars were attached to the leaves as long as they did not dry out.

After the special period, the eradication rate (%) was measured. Extermination rate 100
% means that all the caterpillars died, and 0% means that none of them died.

In this test, for example, production example 1.3.4.7.10.
11.12.21.22.37.38.43.44.5
7.58.60.61 and 63, for example 0.
At a concentration of 0.001%, the extermination rate was 100% after 7 days.

Example B Mosquito Larva Test Test Animal: Aedes aegypti (2nd instar larvae) Solvent = 99 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycol ether To prepare a suitable regulator of the active compound 2 parts by weight of active compound were dissolved in 1.000 parts by volume of solvent containing the above amount of emulsifier. The solution thus obtained was diluted with water to the desired low concentration.

A plurality of plastic containers were filled with the desired aqueous preparation of the active compound and 20 second instar mosquito larvae (Boula) were placed in each container.

Poufura was fed short-day food.

After 1, 8 and 21 days, the eradication rate (%) was measured.

100% means that all the larvae (or their respective pupae) died; 0% means that none died.

In this test, the compounds of Preparation Examples 38 and 63, for example at a concentration of 10-4 ppm, showed a kill rate of 1 after 21 days.
It showed 00%.

Example C Parasitic larva test of Lucilia cuprina Solvent: 35 parts by weight Ethylene glycol monomethyl ether Emulsifier: 35 parts by weight Nonylphenol polyglycol ether Suitable translation of the active compound In order to prepare the active compound, the active compound in question 30 parts by weight were mixed with the above amount of solvent containing the above amount of emulsifier and the resulting stock solution was diluted with water to the desired concentration.

Approximately 20 golden flies (Lucilia cuprina)
) larvae were placed in test tubes containing approximately 2 cm3 of horse meat, and 0.5 ml of the active compound preparation was administered to the horse meat. After 24 hours, the eradication rate (%) was measured. 10
0% means all larvae died, 0% means none died.

For example, at an active compound concentration of 1,000 ppm, the compounds of Production Examples (1) and (4) showed a 100% extermination rate.

Example D Tetranychus test (resistant species)
Solvent: 3 parts by weight dimethylformamide Emulsifier: 1 part by weight alkylaryl polyglycol ether To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amounts of solvent and emulsifier, respectively. The resulting stock solution was then diluted with water to the desired concentration.

Soybean plants heavily infested with spider mites or two-spotted spider mites at all stages of growth (phaseolus vulgur).
is) was immersed in the active compound preparation at the desired concentration.

The eradication rate (%) was measured after a specified period. A score of 100 means that all the mites died, and 0% means that none of them died.

In this test, production examples 2.33.37.38.4;
．． 47.55.56.57.58.60.61 and 63
For example, at a concentration of 0.1%, after 10 days 98%
showed an extermination rate of

Patent applicant Beyer Akchengesellschaft Patent attorney Heikichi Odajima (DE) ■P3341276.6 0 Inventor Wilhelm Stemple Federal Republic of Germany Day 5600 Butzpeltal 1 Inden Birken

Claims (1)

[Claims] 1. Formula (1) (1) where, or represents oxygen or sulfur, R1 represents hydrogen, halogen, nitro, alkyl or alkylthio, and R2, R4 and R5 are the same or or different hydrogen and represents hydrogen or halogen, R3 represents hydrogen, halogen, or nitro, R6 and R7 are the same or different and represent hydrogen, halogen, or alkyl, R8 and R9 are the same or different , and represents hydrogen or halogen, and R10 represents halogenalkylthio or halogenoalkoxy, and (1) if X represents oxygen, and R2, R3, R
4, R6, R8 and R9 represent hydrogen and R7 represents hydrogen or halogen, and (a) R1 and R5 both represent halogen, or (b) R1 represents halogen, nitro or alkyl. , and if R5 represents hydrogen, in these cases the radical R10 always represents halogenoalkylthio, (2) or X represents oxygen or sulfur and R6 represents chlorine and R8 represents hydrogen or chlorine, and R9 represents hydrogen, and R10 represents halogenoalkylthio or halogenoalkoxy, and (a) R1 and R3 represent halogen, and R2,
R4 and Ha represent hydrogen, or (b) R5 and R
3 represents halogen and R1, R2 and R4 represent hydrogen, or (c) R1 and R4 represent halogen and R2, R3 and R5 represent hydrogen;
d) R2 and R5 represent halogen, and R1, R
If 3 and R4 represent hydrogen, in these cases the radical R7 always represents hydrogen or alkyl, 1-phenyl-3-benzoyl-(thio)urea, 2,
In the formula (I) according to claim 1, X represents sulfur or oxygen, and R1 is selected from a series of groups consisting of hydrogen, halogen, nitro, or C1-C6 alkyl or C1-C6 alkylthio. represents one selected group, R2, R4 and R5 are the same or different, and hydrogen,
represents halogen, R3 represents hydrogen, halogen or nitro, R6 and R7 are the same or different, and hydrogen) halogen or C
1 to C6 alkyl group, R8 and R9 are the same or different and represent hydrogen or halogen, and R10 is a halogen having 1 to 4 carbon atoms and having 1 to 4 halogen atoms; represents alkylthio or halogenoalkoxy (preferably chlorosofluoromethylthio, trifluoromethylthio, chlorodifluoromethoxy or trifluoromethoxy), and (1) if X represents oxygen 1 and R2, R3, R
4, R6, R8 and R9 represent hydrogen and R7 represents hydrogen or halogen, and (a) both R7 and R1 represent halogen, or Φ) R1 represents halogen, nitro or C1-C6 alkyl; , and if R5 represents hydrogen, in these cases one radical R10 always represents C1-C4 halogenoalkylthio, and (2) if X represents oxygen or sulfur, 1 and R6 represents chlorine, and R8 represents hydrogen or chlorine, H9 represents hydrogen, and R10 is C1-C4 halogenoalkylthio or 01-
C4 represents halogenoalkoxy, and (a) R1 and R3 represent halogen, and R2,
R4 and R5 represent hydrogen, or (b) R5 and R
3 represents halogen and the hill 1-R2 and R3 represent hydrogen, or (c) R1 and R4 represent halogen and R2, R3 and R5 represent hydrogen, or (d) R2 and R5 represents halogen, and R1
2. Compounds according to claim 1, wherein, if BS and H represent hydrogen, in these cases the radical R1 always represents hydrogen or C1-C6 alkyl. 3. Formula (I) according to claim 1, where X represents oxygen or sulfur, R1 is hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, 1-propyl , n-butyl, 1-
butyl, sec-butyl, tert. -butyl, methylthio, ethylthio, n-globylthio, i-propylthio, n-butylthio, 1-butylthio, sea, -gutylthio, or tert. - represents butylthio, Hl,
R4 and B11 are the same or different and represent hydrogen, fluorine, chlorine, or bromine; R3 represents hydrogen, fluorine, chlorine, bromine, or nitro; R6 and R7 are the same or different; Fluorine, base thread, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec. -butyl,
or tart. -butyl, R8 and R9 are the same or different and represent hydrogen, fluorine, chlorine or bromine, and RIO represents trifluoromethylthio or trifluoromethoxy, and (1) if X is oxygen represents 1 and R2, R3, R
4, R6, R8 and R9 represent hydrogen and R7 represents hydrogen, fluorine, chlorine or bromine, and (a) both R1 and R6 represent fluorine, chlorine and/or bromine or ( b) If R1 represents fluorine, chlorine, bromine, nitro or an alkyl group as mentioned above, and R5 represents hydrogen, in these cases the radical R10 always represents trifluoromethylthio, and (2) or X represents oxygen or sulfur, R6 represents chlorine, R8 represents hydrogen or chlorine, R9 represents hydrogen, and R1O represents trifluoromethylthio or trifluoromethoxy, and ( a) R' and R3 represent fluorine, chlorine or bromine and R4, R4 and R5 represent hydrogen or (b) R5 and R6 represent fluorine, chlorine or bromine and R1, R2 and R4 represents hydrogen, or (c) R1 and R4 represent 1 fluorine, 1 chlorine, or bromine, and R2, R3 and R5 represent hydrogen, or (d) R2 and R5 represent fluorine, chlorine or bromine. and R1, R3 and R4 represent hydrogen, in these cases the radical R7 always represents hydrogen or an alkyl group as defined above. A compound according to any one of claims 1 to 6, wherein X in formula (1) according to claim 1 represents oxygen. 5. Formula (I) according to claim 1, wherein 1 or represents oxygen, R1 represents hydrogen, fluorine, chlorine, bromine, nitro, methyl or methylthio, R2, R4 and R1+ are hydrogen, represents fluorine, chlorine or bromine, R3 represents hydrogen, fluorine, chlorine or nitro, R6 and R7 are the same or different and represent hydrogen, chlorine or methyl, and R8 and R9 are the same or different , and represents hydrogen, fluorine or chlorine, and R10 represents trifluoromethylthio or trifluoromethoquine, and (1) if R2, R3, R4, R6, R8 and R9 represent hydrogen, and R7 represents hydrogen or salt percentage, and (a) R1 and R5 both represent fluorine, chlorine, and/or bromine, or (b) R1 represents fluorine, chlorine, bromine, nitro or methyl, and If R5 represents hydrogen, in these cases the radical R10 always represents trifluoromethylthio, and (2) if R6 represents chlorine and R8 represents hydrogen or chlorine and R9 represents hydrogen; R10 represents trifluoromethylthio or trifluoromethoxy, and (a) R1 and R3 represent fluorine, chlorine and/or bromine, and R2, R4 and R5 represent hydrogen, or (b) ) R5 and R3 represent fluorine, chlorine and/or bromine and R1, R2 and R4 represent hydrogen;
or (c) R1 and R4 represent fluorine, chlorine and/or bromine, and R2, RZ and R1' represent hydrogen, and (d) R2 and R5 represent fluorine, chlorine and/or bromine; and if R1, R3 and R4 represent hydrogen, then in these cases the radical R7 always represents hydrogen or methyl. 6. Formula (1) In the formula, X represents oxygen or sulfur, R1 represents hydrogen, halogen, nitro, alkyl or alkylthio, R2, R4 and R1 are the same or different, and R3 represents 1 hydrogen, halogen or nitro, R6 and R7 are the same or different and represent hydrogen, halogen or alkyl, R8 and R9 are the same or different and represent hydrogen or halogen, and R10 is , represents halogenalkylthio or halogenoalkoxy, and (1) the younger X represents oxygen and R2, R3, R4, R6, R8 and R9 represent hydrogen, and R7 represents hydrogen or halogen, and (a ) R1 and R5 both represent halogen, or (b) R1 represents halogen, nitro or alkyl;
and if R5 represents hydrogen, then in these cases the radical R10 always represents halogenoalkylthio, and (2) if X represents oxygen or sulfur and R6 represents chlorine and R8 represents hydrogen or represents chlorine, and R9 represents hydrogen, and R10 represents halogenoalkylthio or halogenoalkoxy, and (a) R1 and R3 represent halogen, and R2,
R4 and R5 represent hydrogen, or (b) R5 and R
3 represents halogen and R1, R2 and R4 represent hydrogen) or (c) R1 and R4 represent halogen and R2, R3 and R5 represent hydrogen, or (d) R2 and R5 represents halogen, and R1
, R3 and R4 represent hydrogen, in these cases the group R7 always represents hydrogen or alkyl. ) wherein R6, R7, R8, R9 and R10 have the meanings given above; or b) with benzoyl-iso(thio)cyanate of formula (■), if appropriate in the presence of a diluent, where X, R6, R7, R8, R9 and R10 are a substituted phenyliso(thio)cyanate of formula (V) having the meaning as given above, wherein R1, R2, R3, R4 and R5 have the meaning given above; If so, the production process is characterized in that the reaction is carried out in the presence of a catalyst and, if appropriate, in the presence of a diluent. 7. A pest control agent containing at least one compound of formula (■) according to claim 1 or 6. 8. Use of compounds of formula I according to claims 1 or 6 for controlling pests, in particular insects and mites. 9. A method for controlling pests, characterized in that a compound of formula (■) according to claim 1 or 6 is applied to pests, preferably insects or mites, or their habitats. 10. Formula (1) according to claim 1 or 6
1. A method for producing a pest control agent, which comprises mixing a compound of the above with a filler and/or a surfactant.