Carbanilide and means for controlling insects and pathogenic fungi on their basis

 

(57) Abstract:

Describes new carbanilide formula (I), where a refers to the various substituted heterocyclic residues or substituted phenyl group, Q means2-C4-alkenylamine group or a group of the formula-CO-, -CH(OH)-, -CH2ON= C(R10), where R10- C1-C4-alkyl, -(*CH2)n-Y-(CH2)p-, Y is oxygen or a group S(O)r, r is the number 0, 1 or 2, n and p independently of one another denote 0 or 1, character (*) refers to the part of the molecule, which is connected with a phenyl residue aniline fragment, Z - phenyl group, unsubstituted or mono-, disubstituted by identical or different halogen atoms, cyano, C1-C4-alkyl, fluorine-C1-C4-alkyl, or peredelnyj or pyrimidinyl residue, substituted by one or two Cl atoms, F, provided that 2-methyl-N-(2-phenoxyphenyl)-5,6-dihydro-1,4-Ossetian-3-carboxamid excluded. The compounds possess insecticidal and fungicidal activity. Also described means for controlling insects or pathogenic fungi, containing the compound of formula (I). 2 S. p. f-crystals, 6 PL.

The invention relates to new compounds for pest control is to carboxamide, having pesticidal activity (see application for international patent 93/11117, a European patent application A-0545099 And 0589301 and 0589313).

The objective of the invention is to expand the range of compounds possessing pesticidal, in particular fungicide-insecticidal activity.

The problem is solved in carbanilide formula

< / BR>
where a represents a residue of the formula

< / BR>
where R1means alkyl group with the number of carbon atoms one to four, halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five and

R2means a hydrogen atom, halogen,

or

A represents the residue of a formula

< / BR>
where R3means a halogen atom or halogenlampe with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

or

A represents the residue of a formula

< / BR>
where R4means halogenlampe with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

or

A represents the residue of a formula

< / BR>
where R5means halogen atom, alkyl group with carbon atoms of from one to Drogo to five,

or

A represents the residue of a formula

< / BR>
where R6means alkyl group with the number of carbon atoms one to four or halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

X is a sulfur atom, a group SO, SO2,

or

A represents the residue of a formula

< / BR>
where R7means alkyl group with the number of carbon atoms one to four,

or a represents a residue of the formula

< / BR>
where

R8means halogen atom or alkyl group with the number of carbon atoms one to four,

R9means a halogen atom or halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

or

A represents the residue of a formula

< / BR>
Q means alkenylamine group with the number of carbon atoms from two to four, or a group of the formula

< / BR>
< / BR>
where R10means alkyl group with the number of carbon atoms one to four,

or

Q means a group of the formula

-*(CH2)n-Y-(CH2)p-

where Y represents an oxygen atom or a group S(O)r, and r means the number 0, 1 or 2,

n and p nezapyatnannoy with the phenyl residue of aniline fragment,

Z means a phenyl group, unsubstituted or mono-, disubstituted by identical or different halogen atoms, cyano, alkyl group with carbon atoms of from one to four alkyl fluoride group with the number of atoms from one to four and the number of fluorine atoms from one to five, or peredelnyj or pyrimidinyl residue, substituted by one or two chlorine atoms, fluorine, provided that the compound 2-methyl-N-(2-phenoxyphenyl)-5,6-dihydro-1,4-Ossetian-3-carboxamid excluded.

The proposed carbanilide get ways-analogues. For example,

a) as a result of interaction of the acid halides of the formula

< / BR>
where a has the above meanings and

Hal means a halogen atom,

with aniline derivatives of the formula

< / BR>
where Q, Z and m have the above values,

if necessary, the reaction is carried out in the presence of the reagent to bind acid and, if necessary, in the presence of a diluent,

or

b) as a result of interaction derived carbanilide formula

< / BR>
where a has the above meaning,

X2means an oxygen atom or sulfur,

with compounds of the formula

E-(CH2)p-Z (V)

carried out in the presence of the reagent to bind acids and if necessary, in the presence of a diluent,

or

the result of the interaction derived carbanilide formula

< / BR>
where a has the above meanings and

E1means a leaving group,

with compounds of the formula

H-X3-(CH2)p-Z (VII)

where Z and R have the above values and

X3means an oxygen atom or sulfur,

if necessary, the reaction is carried out in the presence of the reagent to bind acid and, if necessary, in the presence of a diluent, and

or

d) as a result of interaction derived carbanilide formula

< / BR>
where a has the above meaning,

with compounds of the formula

E-(CH2)p-Z (V)

where Z and R have the above values and

E stands for a leaving group,

if necessary, the reaction is carried out in the presence of the reagent to bind acid and, if necessary, in the presence of a diluent.

If the parent compounds take the acid chloride 3-deformalisation-2-carboxylic acid and 2-(2-Penilaian-1-yl)-aniline, the reaction according to method (a) can be represented by the following equation:

< / BR>
If the original soedineniya reaction according to method (b) can be represented by the following equation:

< / BR>
If the parent compounds take 2-bromoethylamine 1-methyl-3-cryptomaterial-4-carboxylic acid and 4-chlorothiophenol, the reaction according to method (C) can be represented by the following equation:

< / BR>
If the parent compounds take 2-hydroxymethylene 1-methyl-3-cryptomaterial-4-carboxylic acid and 2,4-dimethylbenzylamine, the reaction according to method (g) can be represented by the following equation:

< / BR>
The acid halides used as starting compounds for the reaction according to method (a) is represented by formula (II). In this formula a preferably has the same values, and preferred values And relevant to the invention the compounds of the formula (I), which were presented previously in connection with their description. The symbol Hal preferably denotes fluorine atom, chlorine or bromine.

The acid halides of the formula (II) are known or they can be obtained in General by known methods, for example, materials of the international patent application 93/11117, applications for European patents And 545099, And-0589301 and 0589313.

Derivatives of aniline, necessary for the reaction according to method (a) quality same values that and the preferred values of these balances in the relevant invention the compounds of the formula (I), which were presented previously in connection with their description.

Derivatives of aniline of formula (III) are known or they can be obtained in General by known methods, for example, materials of the international patent application 93/11117, applications for European patents And 0545099 And 0589301 And 0371950 and 0292990.

As a means to bind the acid with the reaction according to method (a) can be used for such reactions of inorganic and organic bases. Preferably this can be used hydroxides of alkali and alkaline earth metals, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or ammonium hydroxide, carbonates of alkali metals, for example sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, acetates, alkali or alkaline earth metals, for example sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclo, Diisobutylene, databaseconnect. But the synthesis can be applied in the reaction so that so he simultaneously acted as a means for binding the acid.

As a diluent in the reaction according to method (a) it is possible to use all customary inert organic solvents. Preferably can be applied not halogenated or halogenated aliphatic, alicyclic or aromatic hydrocarbons, for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers like diethyl ether, diisopropyl ether, methyl-tert.-butyl ether, methyl-tert.-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; NITRILES such as acetonitrile, propionitrile, n-butyronitrile, isobutyronitrile or benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or hexamethylphosphorotriamide; such esters as methyl ester of acetic acid or ethyl ester of acetic acid; such sulfoxidov as dimethyl sulfoxide, or sulfones such as sulfolane.

When carrying out the reaction according to method (a) temperatureprofile in the range from 10oWith up to 100oC.

As if the reaction according to method (a), and accordingly the invention methods from (b) to (g), the work is carried out in General under atmospheric pressure. But in each case it is not excluded the possibility of carrying out reactions at elevated or at reduced pressure.

When carrying out reaction according to the method of (a) one mol of gelegenheid acid of General formula (II) are added in the General case one mol or an excess of aniline derivative of the formula (III), and from one to three moles of a means for binding the acid. But it does not exclude the possibility of using components of the reactions at different ratios. The selection of the target product flows through conventional methods. In General this is done by adding to the reaction mass of water, separating the organic phase and pariva her after drying under reduced pressure. Obtained by the process of evaporation, the residue may be purified from impurities that might appear, in the usual ways, for example by chromatographytandem or recrystallization.

Used as initial products for the reaction according to method (b) derivatives carbanilide in General are defined by the formula (IV). In this formula Gusich the invention the compounds of the formula (I), which were presented previously in connection with their description. Preferably X2means an oxygen atom or sulfur.

Derivatives carbanilide formula (IV) are known or they can be obtained by known methods. For example, the compounds of formula (IV) obtained from the acid halides of the formula

< / BR>
where a and Hal have the above values,

as a result of their reaction with aminophenols or aminothiophenol formula

< / BR>
where X2has the above value,

optionally, in the presence of means for binding the acid, for example potassium carbonate or a tertiary amine, and, if necessary, in the presence of an inert organic solvent, for example in the presence of toluene, at temperatures from 20oWith up to 150oC.

Used as initial products for carrying out the reactions according to the above method aminophenols or respectively aminothiophenol formula (XI) are known or they can be obtained by known methods.

Used as initial products for reactions performed according to the method (b) compounds defined by formula (V). In this formula, Z and R are preferably the same values, chili described previously in connection with their description. Preferably E. means chlorine atom, bromine, iodine, methylsulfonylmethane, coolsolutionsgroup or a residue of formula R29-O-SO2-O or R29-O-CO-O-, where R29means alkyl group with the number of carbon atoms one to four, preferably it is a methyl or ethyl group.

The compounds of formula (V) are also known or they can be obtained by known methods.

When carrying out the reaction according to method (b) as a means for binding the acid can be used for such reactions of inorganic and organic bases. Preferably this can be used hydrides of alkali and alkaline earth metals, their hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, tert.-butyl potassium, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, and ammonium compounds such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N,N-dimethylbenz is replaced or databaseconnect.

As a diluent in the reaction according to method (b) it is possible to use all customary inert organic solvents. Preferably it is possible to use all solvents which have already been mentioned in connection with the description of the method (a).

When carrying out the reaction according to method (b) temperature may vary within wide limits. In General operate in temperatures ranging from -20oC to +150oWith, preferably in the temperature range from -10oC to +120oC.

When carrying out the reactions according to the method (b) one mole of a derived carbanilide formula (IV) taken in General from one to two moles of the compounds of formula (V) and, if necessary, an equivalent amount or an excess of means for binding the acid. The selection of the target product flows through conventional methods. In General this is done by adding to the reaction mass of water, separating the organic phase and pariva her after drying under reduced pressure. If the reaction was used miscible with water, the solvent, the target product usually precipitates as a solid substance upon dilution of the reaction mixture with water. In this case, the selection of the target product, as a rule, PR is able to contain, conventional methods, such as chromatographytandem or recrystallization.

Used as initial products for carrying out the reactions according to the above mentioned method (b) derivatives carbanilide defined in General formula (VI). In this formula a preferably has the same values as the values for this residue in the corresponding invention the compounds of the formula (I), which were presented previously in connection with their description. Preferably E1means chlorine atom, bromine, iodine, methylsulfonylmethane, coolsolutionsgroup or a residue of formula R29-O-SO2-O - or R29-O-CO-O-, where R29means alkyl group with the number of carbon atoms one to four, preferably it is a methyl or ethyl group.

Derivatives carbanilide formula (VI) are known or they can be obtained by known methods.

Used as initial products for the reaction according to method (C) compounds in General are defined by the formula (VII). In this formula, Z and R are preferably the same values, and preferred values for these residues and index relevant to the invention the compounds of the formula (I), which tx2">

The compounds of formula (VII) are also known or they can be obtained by known methods.

As a means to bind the acid with the reaction according to method (C) can be used for such reactions of inorganic and organic bases. Preferably this can be used all acceptors acids, which have already been transferred in connection with the description of the method (b).

As a diluent in the reaction according to method (C) can be used water, as well as all other conventional inert organic solvents. Preferably can be applied not halogenated or halogenated aliphatic, alicyclic or aromatic hydrocarbons, for example benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers like diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones such as acetone, butanone or methyl isobutyl ketone; NITRILES such as acetonitrile, propionitrile or benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is silt ether acetic acid; such sulfoxidov as dimethyl sulfoxide; alcohols such as methanol, ethanol, n-propanol or isopropanol, onomatology ether of ethylene glycol, monotropy ether of ethylene glycol, onomatology ether of diethylene glycol, monotropy ether of diethylene glycol, mixtures thereof with water or water alone.

And when carrying out the reactions according to the method (b) temperature may vary within wide limits. In General operate in temperatures ranging from -20oC to +150oWith, preferably in the temperature range from -10oC to +120oC.

When carrying out the reactions according to the method (b) for one mole of the derivative carbanilide formula (VI) take in the General case, from one to two moles of the compounds of formula (VII) and, if necessary, an equivalent amount or an excess of means for binding the acid. The selection of the target product is conducted according to conventional methods.

Used as initial products for carrying out reactions on the way (g) derivatives carbanilide defined in General formula (VIII). In this formula, And has the same values as the values for this residue in the corresponding invention the compounds of the formula (I), which were presented previously in connection with their description.

>/P>As a means to bind the acid with the reaction according to method (g) can be used with all conventional for such reactions of inorganic and organic bases. Preferably this can be used all acceptors acids, which have already been transferred in connection with the description of the method (b).

As a diluent in the reaction according to method (g) it is possible to use all customary inert organic solvents. Preferably, you can use any of the listed preferred diluents that have already been transferred in connection with the description of the method (b).

And when carrying out the reactions according to the method of (g) temperature may vary within wide limits. In General operate in temperatures ranging from -20oC to +150oWith, preferably in the temperature range from -10oC to +120oC.

When carrying out the reactions according to the method of (g) per mol of the derived carbanilide formula (VIII) take in the General case, from one to two moles of the compounds of formula (V) and, if necessary, an equivalent amount or an excess of means for binding the acid. The selection of the target product is conducted according to conventional methods.

The task also interconnect pathogenic fungi.

Fungicides are used to protect plants from fungi such as Plasmodio-phoromycetes, Oomycetes, Chytridiomycota, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

As an example, but not limited volume of claims, it is possible to enumerate some pathogens of fungal diseases which belong to the above groups of microorganisms:

mushrooms of the genus Xanthomonas, for example Xanthomonas campestris pv. Oryzae;

mushrooms of the genus Pseudomonas, such as Pseudomonas syringae pv. lachrymans;

mushrooms of the genus Erwinia, for example, Erwinia amylovora;

fungi of the genus Pythium, for example Pythium ultimum;

mushrooms of the genus Phytophtora, for example, Phytophtora infestans;

mushrooms of the genus Pseudoperonospora, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;

mushrooms of the genus Plasmopara, for example, Plasmopara viticola;

mushrooms of the genus Bremia, for example, Bremia lactucae;

mushrooms of the genus Peronospora., for example, Peronospora. pisi or Peronospora. brassicae;

mushrooms of the genus Erysife, for example Erysife graminis;

mushrooms of the genus Sphaerotheca, for example, Sphaerotheca fuliginea;

mushrooms of the genus Podosphaera, for example, Podosphaera leucotricha;

mushrooms of the genus Venturia, for example, Venturia inaequalis;

mushrooms of the genus Pyrenophora, for example, Pyrenophora teres or Pyrenophora graminea (form conidia Cereals, synonym - Helmintosporium);

mushrooms of the genus Cochliobolus, for example, Cochliobolus sativus (form conidia Cereals, synonym - Helmintosporium);

mushrooms of the genus Uromyces, for example, Uromyces appendiculatus;

mushrooms of the genus Puaries;

mushrooms of the genus Ustilago, for example, Ustilago nuda or Ustilago avenae;

mushrooms of the genus Pellicularia, for example, Pellicularia sasakii;

mushrooms of the genus Pyricularia, for example, Pyricularia orizae;

fungi of the genus Fusarium such as Fusarium culmorum;

fungi of the genus Botrytis, for example Botrytis cinerea;

mushrooms of the genus Septoria, for example, Septoria nodorum;

mushrooms of the genus Leptosphaeria, for example, Leptosphaeria nodorum;

mushrooms of the genus Cercospora, for example, Cercospora canescens;

mushrooms of the genus Altemaria, for example Altemaria brassicae;

mushrooms of the genus Pseudocercosporella, for example, Pseudocercosporella herpotrichoides.

These active substances are well tolerated by plants required for combating plant diseases concentrations, which allows for the processing of ground plant parts and seed, seedlings and soil.

Especially good results are achieved with the appropriate use of the invention the active substances to combat diseases of the vine, fruit and vegetable crops, caused by, for example, fungi of the genus Venturia, Podosphaera, Phytophtora and Plasmopara. With good success, you can apply them and to fight disease of rice, caused by, for example, fungi of the genus Pyricularia.

In the protection of materials relevant to the invention substances can be used for the protection of technical materials from Gnani the Xia inanimate materials, prepared for use for technical purposes. For example, among the technical materials protected under the relevant invention the active substances from microbial damage or damage, you should call adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastics, lubricants, refrigeration equipment and other materials that can become a breeding ground for microorganisms and destroyed them. In a number of protected materials also includes elements of the production systems, for example systems with circulating cooling water, the functioning of which may be infringed by the reproduction of microorganisms. In the framework of the present invention to protect technical materials are preferably adhesives, glues, paper and cardboards, leather, wood, paints, lubricants for refrigeration and liquid fluids, in the first instance the wood.

Among the microorganisms that can cause destruction or change the properties of engineering materials, should be highlighted, for example, fungi, yeasts, algae and slime mold. To meet the diversified mushrooms, the fungi that cause discoloration and destruction of wood (basidiomycetes), and slime mold and algae.

Specifically, should be called, for example, microorganisms such genera as

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniphora, for example Coniphora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride.

Corresponding to the invention the active substance, which are well tolerated by plants and which differ favorable indicator of toxicity towards warm-blooded animals, can be used for pest control, representing the animal world, preferably with insects encountered in the practice of agriculture, in forestry, in the gardens, they can also find application in the field of hygiene, veterinary and medicine, as well as where you need protection materials and stored goods. These substances exert their activity against species with normal sensitivity and resistant species, they are also the pits, representing wildlife include the following:

From the order Isopoda, for example Oniscus aselus, Armadillidium vulgare, Porceflio scaber.

From the order Diplopoda, for example Blaniulus guttulatus.

From the order Chilopoda, for example Geophilus carpophagus, Scutigera spec.

From the order Symphyla, for example Scutigerella immaculata.

From the order Thysanura, for example Lepisma saccharina.

From the order Collembola, for example Onychiurus armatus.

From the order Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order Dermaptera, for example Forficula auricularia.

From the order Isoptera, for example Reticulitermes spp.

From the order Anoplura, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order Mallophaga, for example, Trichodectes spp., Damalinea spp.

From the order Thysanoptera, for example Hercinothrips femoralis, Thrips tabaci.

From the order Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomysus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saisettia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederaonomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. , Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp. , Euxoa spp., Feltia spp., Earias insulana, Heliotis spp., Spodoptera exigua, Mamestra brassicae, Panolis flamea, Prodenia litura, Spodoptera spp. , Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria melonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp. , Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp. , Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costellytra zealandica.

From the order Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp. , Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From squad Syphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp.

These active substances depending on their physical and, suspensions, powders, foams, pastes, granules, aerosols, can produce finely dispersed encapsulated drugs in polymeric membranes, they can also enter into the composition of the polymer coating for seed, and formulations of ultra low volume spraying and in the preparative form, forming the aerosol when heated.

These preparative forms prepared by known methods, for example by mixing the active principles with diluents, i.e. liquid solvents, pressurized liquefied gases and/or solid carriers, optionally with the use of surface-active substances such as emulsifying means and/or dispersing means and/or blowing means. In the case of use as diluent water can be applied, for example, and organic solvents as additional solvents (solubilization). In the role of liquid solvents can be mainly aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphaticity or glycol, as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, solvents with high polarity, such as dimethylformamide and dimethylsulfoxide, and water. Under liquefied gaseous diluents or substances carriers understand such liquids at normal temperature and under normal pressure are in the gaseous state. This is, for example, propellants for aerosol compounds such as halogen-substituted hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. As solids carriers can be used, for example, crushed rocks, such as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or infusoria earth, and ground synthetic minerals such as highly disperse silicic acid, alumina and silicates. As solids carriers for granular preparative forms can be, for example, crushed and fractionated natural minerals such as calcite, marble, pumice, thick, dolomite, and synthetic granules based on

inorganic and organic crushed materials, and also granules of organic is este emulsifying and/or foam-forming means can be, for example, nonionic and anionic emulsifiers, such as esters of fatty acids and oxides, ethers of fatty alcohols and oxides, such as ethoxylated ALKYLPHENOLS, alkyl sulphonates, alkyl sulphates, arylsulfonate, as well as protein hydrolysates. Dispersing means can be, for example, ligninase sulfite liquor and methylcellulose.

To improve the adhesion preparative forms you can use such components as carboxymethylcellulose, natural and synthetic powdered, granular or latex polymers, such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as Catalina and lecithins, and synthetic phospholipids. As other additives can be mineral and vegetable oils.

Can also be used colorants such as inorganic pigments, for example iron oxide, titanium oxide, blue ferrocyanides, and organic dyes such as alizarin and metallophthalocyanine dyes, azo dyes, and trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The content of active substances in preparative in the shadow of the active substance can be included in the preparative forms as the only active substance or in a mixture with known fungicides, the bactericides, acaricides, nematicides or insecticides, in order, for example, to widen the spectrum of action or to prevent the development of resistance. In many cases achieved synergies, i.e. the effectiveness of the mixture is higher than the efficiency of individual components.

As components for the preparation of mixed drugs can be used in the following preparations.

Fungicides:

Aldemar, aspropirgos, lampropeltis-potassium, andapril, anilazine, azaconazole, AZOXYSTROBIN;

benalaxyl, Benadryl, benomyl, benzamycin, benzamycin-isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, butiaba,

the calcium polysulfide, capsaicin, captafol, Captan, carbendazim, carboxin, carvon, chinomethionat, chlorbenside, chlorbenzol, chloroneb, chloropicrin, CHLOROTHALONIL, chlozolinate, clothingon, kurane, having cymoxanil, tsyprokonazolu, cyprodinil, zeroforum;

debaker, dichlorophen, diclobutrazol, dichlofluanid, declomycin, dicloran, dietphenterm, difenoconazol, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, datalists, dithianon, dodemont, milked, fenarimol, fenbuconazole, fanforum, penetapan, fenpiclonil, fenpropidin, fenpropimorph, fenolovaya, fenoloogilised, ferbam, verison, fluazinam, flamethower, fluorone, fluquinconazole, flurried, flusilazol, glucolipid, flutolanil, flutriafol, folpet, foretelling, volatilaty, phtalic, fuberidazole, parallaxis, parameter, percarbonic, vorconizole, vorconizole, pharmacyclics;

guazatine;

hexachlorobenzene, hexaconazole, hymexazol;

imazalil, kabekona, iminoctadine, iminoctadine, iminoctadine, iodosorb, ipconazole, iprobenfos (Biophysics Institute), iprodion, arunamarin, isoprothiolane, isovaleryl;

kasugamycin, kresoximmethyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxymed and Bordeaux mixture,

marcopper, MANCOZEB, MANEB, severinson, mepanipyrim, mepronil, metalaxyl, metconazole, metasurfaces, mefenoxam, metiram, matomela, metalhawk, millionizer, myclobutanil, mickleton;

the Nickel dimethyldithiocarbamate, nitratenitrogen, nuarimol,

operas, oxadixyl, oxamate, oxolinic, oxycarboxin, oxidation;

paclobutrazol, peyratout, penconazole, propanedinitrile, propiconazol, propineb, pyrazophos, pirivenas, Pyrimethanil, pyroquilon, proxyfor;

rinconsol, quintozene (PCNB);

sulfur and preparations based on sulfur,

the tebuconazole, telital, tecnazene, tetcyclacis, tetraconazole, thiabendazol, tilian, leflunomid, thiophenemethyl, thiram, dioxime, cyclophosphates, tolylfluanid, triadimefon, triadimenol, triazolyl, triazoxide, trihemic, tricyclazole, tridemorph, triflumizole, triforine, triticonazole;

uniconazole;

validamycin And, vinclozolin, wineconsole;

Suriname, zineb, Tsira, and

dagger G,

OK-8705,

OK-8801,

2', 6'-dibromo-2-methyl-4'-triptoreline-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,

2,6-dichloro-N-(4-trifloromethyl)-benzamid,

2 aminobutane,

2-phenylphenol (ORR),

8-hydroxyanisole,

CIS-1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-cycloheptanol,

(5RS, 6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazole-1-yl)-3-octanone,

-(2,4-dichlorophenyl)--methoxy--methyl-1H-1,2,4-triazole-1-ethanol,

-(1,1-dimethylethyl)--(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethynyl]-1H-imidazole,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy] -2,5-thiophencarboxylic,

2-[(phenylamino)-carbonyl]-hydrazide N-xanthene-9-carboxylic acid,

O-methyl-S-phenyl-phenylpropionaldehyde,

N-(5-chloro-2-were)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-ndimethylacetamide,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-alanon-O-(phenylmethyl)-oxime,

N-(2,6-dimetilfenil)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-ndimethylacetamide,

hydrochloride CIS-4-[3-[4-(1,1-dimethylpropyl)-phenyl]-2-methylpropyl]-2,6-dimethylmorpholine,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2.5-pyrrolidinedione,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidino,

1-[[2-(4-chlorophenyl)-3-phenyloxirane]-methyl]-1H-1,2,4-triazole,

sodium salt metanarrative,

2-(2,3,3-tried-2-propenyl)-2H-tetrazol,

N-[3-chloro-4,5-bis-(2-propenyloxy)-phenyl]-N'-methoxy-methanimidamide,

-(5-methyl-1,3-dioxane-5-yl)--[[4-(trifluoromethyl)-phenyl] -methylene] -1H-1,2,4-triazole-1-ethanol,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

N-(2,6-dimetilfenil)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-ndimethylacetamide,

3,4-dichloro-1-[4-(deformedarse)-phenyl]-1H-pyrrole-2,5-dione,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

sodium salt of N-formyl-N-hydroxy-DL-alanine,

N-(4-cyclohexylphenol)-1,4,5,6-tetrahydro-2-pyrimidinamine,

4-methyl-tetrazolo[1,5-a]hinzelin-5(4H)-he,

2 is fenil)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzosulfimide,

methyl ester of N-(chloroacetyl)-N-(2,6-dimetilfenil)-DL-alanine,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidine]-pyridine,

2-[(1-methylethyl)sulfonyl]-5-trichloromethyl)-1,3,4-thiadiazole,

Spiro[2H]-1-benzopyran-2,1'(3 N)-isobenzofuran-3'-Oh,

methyl ester of N-(2,6-dimetilfenil)-N-(5-isoxazolidinone)-DL-alanine,

bicarbonate of potassium,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolane-2-yl]-methyl]-1H-imidazole,

1-[(diiodomethyl)-sulfonyl]-4-methylbenzol,

2-bromo-2-(methyl bromide)-pentanedinitrile,

2-[[6-deoxy-4-O-(4-O-methyl-D-glycopyranosyl)--D-glyukopiranozil] -amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

methyl ester 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1 H-imidazol-5-CT-oil acid,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

O,O-diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylenedithio,

-(2,4-dichlorophenyl)--fluorine--propyl-1H-1,2,4-triazole-1-ethanol,

3-(1,1-dimethylpropyl)-1-oxo-1H-inden-2-carbonitril,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

S-methyl ester of 1,2,3-benzothiadiazole-7-thiocarbonic acid,

N-(6-methoxy)-3-pyridinyl-cyclopropanecarboxamide,

3,5-dichloro-N-[cyan-[(1-methyl-2-promotility)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5] decane-2-methanamine,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxylic.

Insecticides:

the abamectin, AC 303 630, Arafat, acrinathrin, alankar, aldicarb, alpha metrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos And, azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, betacellulin, bifenthrin, VRMS, papenbrock, bromophos And, bofenkamp, buprofezin, butocarboxim, butylparaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, CGA 157419, CGA 184699, cloethocarb, chlorethoxyfos, Chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, carismatic, claritin, clofentezine, cyanophos, cicloprofen, cyfluthrin, cigalotrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, declivous, dicrotophos, diation, diflubenzuron, dimethoate, dimethylene, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ation, etofenprox, ethoprophos, etrimfos,

fenamiphos, fenazaquin, fanbot-olowookere, fenitrothion, fenobucarb, fanatical, fenoxycarb, fenpropathrin, ,, flavandiols, fluvalinate, fonofos, formation, fosthiazate, tupfenrock, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidacloprid, iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda-cigalotrin, lufenuron,

Malathion, mecarbam, mevinphos, resolvents, metaldehyde, methacrifos, metamidophos, mitigation, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemeton M, oxidants,

parathion And parathion M, permethrin, pentat, Fort, fozalon, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos And, profenofos, promecarb, propafol, propoxur, prothiofos, procoat, pymetrozine, pyraclofos, peradventure, prismatron, feverfew, pyridaben, pyrimidifen, pyriproxifen,

finalpos,

RH 5992,

coalition, sabots, selflove, sulfotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, terram, terbufos, tetrachlorvinphos, titanox, thiodicarb, thiofanox, thiometon, thionazin, thuringiensis, tralomethrin, triuralin, triazophos, treasure, trichlorfon, triflumuron, trimeter, validation, CMS, killchar, decamethrin,

These active substances are used both in pure form and in the form of their formulations or forms prepared from these formulations, such as ready-to-use solutions, suspensions, dusty for spraying, pastes, wettable powders, means for powder and granulates. They are used in the usual ways, for example by pouring, sprinkling, spraying, spreading, dusting, they can be applied in the form of foams, coatings, or other methods. These active substances can also be applied in the form of compositions for ultra-low volume spraying, in addition, the active substance and formulation based on them can be injected into the soil. With their help it is possible to conduct processing of seed plant material.

When the processing of individual parts of plants the concentration of active substance in ready-to-use forms can vary within wide limits. In General, these concentrations are in the range from 1 to 0.0001 wt.%, preferably from 0.5 to 0.001 wt.%.

In the General case for processing of seed material of the active substance is taken in an amount of from 0.001 to 50 g per kilogram of seed, preferably from 0.01 to 10 g

Soil concentrations of active substances should is used for the protection of technical materials, these active substances are contained in General in amounts of from 1 to 95%, preferably from 10 to 75%.

The concentration in which the relevant of the invention the active substance, dependent on species and habitats, destroy microorganisms, and on the composition of the protected material. The optimal number of substances can be determined in a series of experiments. In General they are used in concentrations of from 0.001 to 5 wt.%, preferably from 0.05 to 1.0 wt.% based on the weight of the protected material.

The efficacy and spectrum of biological activity used to protect materials relevant to the invention the active substances or correspondingly produced from these funds, concentrates or in the most General sense preparative forms can be improved, if this will be added to other compounds with antimicrobial activity, fungicides, bactericides, herbicides, insecticides or other active ingredients to broaden the spectrum of biological activity, or to achieve special effects, such as additional protection against insects. Such mixtures can have a broader spectrum of biological activity than the corresponding invention vesmir pests, may be in the formulation and in the prepared from these formulations form ready-to-use compositions in the form of a mixture with synergists. Synergistic referred to as compounds that increase the effectiveness of active substances. Thus he added the synergist may be inactive connection.

The content of active substance in ready-to-use compositions derived from marketed preparative forms may vary within wide limits. The concentration of active substance in ready-to-use compositions may lie in the range from 0.0000001 to 95 wt.% the active substance, preferably from 0.0001 to 1 wt.%.

Practical application in the normal way, the corresponding ready to use composition.

Obtaining and applying relevant to the invention substances illustrate the following examples.

Synthetic examples

Example 1

< / BR>
Method (a)

To a solution of 0.3 g (0,0015 mol) of 2-(2-phenyl-ethen-1-yl)-aniline in 2 ml of toluene at room temperature was added a solution of 0.15 g (0,0015 mol) of triethylamine in 10 ml of toluene. To the resulting mixture at room temperature under stirring was added 0.33 g (0,0015 mol) of chlorine is Lieut stirring at this temperature for 2 hours. For separation of the reaction mixture it is cooled to room temperature and add it to the water. The organic phase is separated, dried over sodium sulfate and then evaporated at a temperature of 60oC and under reduced pressure. The obtained residue chromatographic on silica gel, using as eluent sulphuric ether. After evaporation of the eluate gain of 0.53 g (95% of theory) of 2-(2-phenyl-ethen-1-yl)-anilide 3 deformedarse-thiophene-2-carboxylic acid in the form of a solid substance with so pl. 80-82oC.

Obtaining initial substances

< / BR>
To a mixture of 4.2 g (0,022 mol) of 3-deformedarse-thiophene-2-carboxylic acid in 45 ml of toluene was added with stirring 3.1 g (0,026 mol) of thionyl chloride at a temperature of 80oC. After the addition, the reaction mass is heated to 90oC and stirred for further 2 hours at this temperature. In conclusion, the reaction mass is evaporated at a temperature of 60oWith under reduced pressure. Thus obtain 4.6 g (98.3% of theory) of acid chloride of 3-deformedarse-thiophene-2-carboxylic acid in the form of butter.

< / BR>
To a mixture of 2.4 g (0.012 mol) of the methyl ester of 3-deformedarse-thiophene-2-carboxylic acid and 5 ml of ethanol at room temperature was added a solution of 2 g (0,048 mol) g is Assu by adding 50 ml of water and extracted several times with methylene chloride. By adding diluted hydrochloric acid set in the aqueous phase of a pH value of from 2 to 3, drop down solid is sucked off, washed with water and dried. In this way we obtain 2.2 g (90,15% of theory) of 3-deformedarse-thiophene-2-carboxylic acid in the form of a solid substance with so pl. 98-100oC.

< / BR>
To a mixture of 10 g (0,063 mol) of methyl ester of 3-hydroxy-thiophene-2-carboxylic acid and 90 ml of toluene at room temperature was added a solution of 5.1 g (to 0.127 mol) of sodium hydroxide in 8 ml of water. The reaction mass is heated with stirring to a temperature of 90oTo give 1.1 g of the bromide tetrabutylphosphonium, within 30 minutes passed and 16.4 g (0,189 mol) of diperchlorate and then continue stirring for 1 hour at 90oC. In conclusion, cooled the reaction mass to room temperature, water is added, the organic phase is separated, dried over sodium sulfate and then evaporated at 50oWith under reduced pressure. The resulting residue is purified by chromatographytandem on silica gel, elwira with a mixture of cyclohexane and ethyl acetate in a ratio of 3: 1. After evaporation of the eluate obtain 4.1 g (31,3 from theory) of methyl ester of 3-deformedarse-thiophene-2-carboxylic acid in the form of butter.

< / BR>
To a mixture of 12.9 g (0,057 mol) 1-phenyl-2-(2-nitrophenyl)-Atena and 210 ml of 17% aqueous hydrochloric acid at room temperature type of 38.7 g of powder of tin and slowly heated to the boiling point. Boiled for 2 hours under reflux, cooled to room temperature and repeatedly extracted with ethyl ether. The organic phase is evaporated under reduced pressure, to the residue water is added, the resulting mixture by the addition of dilute aqueous sodium hydroxide solution set neutral reaction and then extracted several times with methylene chloride. The combined organic phases are dried over sodium sulfate and evaporated under reduced pressure. The resulting residue is purified by chromatographytandem on silica gel, elwira with a mixture of cyclohexane and ethyl acetate in a ratio of 3:1. After evaporation of the eluate obtain 8.5 g (76,4% of theory) of 2-(2-Penilaian-1-yl)-aniline in the form of a solid substance with so pl. 80oC.

Example 2

< / BR>
Method (b)

To a mixture of 1.0 g (0,0035 mol) of 2-hydroxyphenylacetate 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid, of 0.53 g (to 0.0039 mol) of potassium carbonate and 10 ml of acetonitrile is added with stirring at room temperature 0,57 g (0,0037 mol) of 2,4-dimethy the second temperature. In conclusion, the reaction mass is then cooled to room temperature, add water, suck dropdown precipitate, washed with water and dried at a temperature of 50oWith under reduced pressure over phosphorus pentoxide. This way we obtain 1.2 g (85% of theory) of 2-(2,4-dimethylbenzylamine)-anilide 1-methyl-3-cryptomaterial-4-carboxylic acid in the form of a solid substance with so pl. 123-125oC.

Range1H-NMR (deuterochloroform with tetramethylsilane was): =3,945 (C., 3H); 5,082 (S., 2H) ppm.

Getting the initial connection

< / BR>
To a mixture of 2.4 g (0,022 mol) of 2-aminophenol and 80 ml of toluene is added with stirring at a temperature of 100oTo a solution of 5.0 g (0,024 mol) of acid chloride of 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid in 25 ml of toluene. The reaction mass is still stirred for 4 hours at a temperature of 100oC, then cooled to room temperature, water is added, the precipitation is sucked off and dried at a temperature of 50oWith under reduced pressure. In this way gain of 5.4 g (86.1% of theory) of 2-hydroxyphenylacetate 1-methyl-3-cryptomaterial-4-carboxylic acid in the form of a solid substance with so pl. 191oC.

Range1H-NMR (deuterochloroform of oxygenenriched 1-methyl-3-cryptomaterial-4-carboxylic acid in 15 ml of dimethylformamide at the temperature of 15oWhen mixing, slowly add 0,347 mg of 80% sodium hydride (in paraffin). Thereafter, the resulting mixture with stirring, added dropwise to a solution of 1.41 g (10.5 mmol) of 4,5,6-cryptosporidia in 15 ml of dimethylformamide at a temperature of 0oC. After the addition, the reaction mass is still 1 hour and stirred at a temperature of 0oWith and then evaporated away under reduced pressure the solvent. To the resulting residue are added water and intensively stirred for two minutes. The obtained solid is sucked off, dried and recrystallized from toluene. In this way receive 3,43 g (81% of theory) of 2-(4,5-giftability-6-oxy)-anilide 1-methyl-3-cryptomaterial-4-carboxylic acid in the form of a solid substance with so pl. 197oC.

By analogy with the above methods are also listed in the following further table 1 carbanilide formula

< / BR>
The following examples illustrate the biological activity of the proposed tools.

An example of a

Test protective effect against the pathogen Podosphaera (Apple).

1 wt. some of the listed in the table of active substance is mixed with 47 weight parts of acetone as Rustica concentrate with water to a concentration of the active substance, 100 h/million

To study the contact activity sprinkle young plants composition prepared with the active substance to the formation of droplets of moisture on the plants. After drying the applied solution plants inoculant, Audrina their conidia of the pathogen of powdery mildew of Apple Podosphaera leucotricha.

The plants installed in the greenhouse with a temperature of 23oC and with a relative humidity of about 70%.

10 days after inoculation to assess the condition of plants in %. 0% means an activity that corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

The active substance and the results of the experiments are shown in table 2.

Example B

Test protective effect against the pathogen Venturia (Apple).

1 wt. some of the listed in table 3, the active substance is mixed with 47 wt. parts of acetone as solvent and 3 wt. parts alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to a concentration of the active substance, equal to 100 h/million

To study the contact activity sprinkle young plants Besenova solution inoculant plants with an aqueous suspension of conidia of the pathogen of Apple scab Venturia inaequalis and leave them for 1 day in an incubation box at a temperature of 20oC and a relative humidity of 100%.

The plants installed in the greenhouse with a temperature of 23oC and with a relative humidity of about 70%. 12 days after inoculation to assess the condition of plants in %. 0% means an activity that corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

The active substance and the results of the experiments are given in table 3.

The example IN

Test protective effect against the pathogen Pyrenophora teres (barley).

1 wt. some of the listed in table 4 of the active substance is mixed with 10 wt. parts of N-methylpyrrolidone as solvent and 0.6. parts alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to the desired concentration.

To study the contact activity sprinkle young plants prepared by the preparation of the active substance is applied at a rate of application of active substances, equal to 125 g/ha

After drying the applied solution inoculant plants with a suspension of conidia of Pyrenophora teres.

Plants left for 48 hours in an incubation box at tempera is uroy about 20oC and with a relative humidity of about 80%.

7 days after inoculation to assess the condition of plants in %. 0% means an activity that corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

The active substance and the results of the experiments are given in table 4.

Example D

Test for protective action in relation to the R-strain of Pseudocercosporella herpotrichoides (wheat).

1 wt. part of the active substance of example 199 mixed with 10 wt. parts of N-methyl-pyrrolidone as solvent and 0.6. parts alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to the desired concentration.

To study the contact activity sprinkle young plants prepared by the preparation of the active substance is applied at a rate of application of active substances, equal to 250 g/ha

After drying the applied solution inoculant plants at the base of the stem spores of R-strain of Pseudocercosporella herpotrichoides.

Plants set in a greenhouse at a temperature of about 10oC and a relative humidity of about 80%.

21 days after inoculate the data control plants, and 100% means that the plants are not infected.

In this experiment, the activity is 90%.

Example D

Test on the pest Plutella

1 wt. some of the listed in the table of active substance is mixed with 7 wt. parts of dimethylformamide as solvent and 1 wt. part alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to a concentration of the active substance, equal to 0.1%.

Cabbage leaves (Brassica oleracea) are treated by immersion in ready-to-use composition with the desired concentration of the active substance and still wet the leaves carry the larvae of cabbage moth (Plutella maculipennis).

After the desired time determine the level of mortality. 100% means that all dead caterpillars, and 0% means that no died no one caterpillar.

The active substance and the results of the experiments are given in table 5.

Example E

Test on the pest Spodoptera

1 wt. part of the active substance of example 120 is mixed with 7 wt. parts of dimethylformamide and 1 wt. part alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to a concentration of the active substance, equal to 0.1%.

Fox is e wet leaves carry Cutworm caterpillars (Spodoptera frugiperda).

After the desired time determine the level of mortality. 100% means that all dead caterpillars, and 0% means that no died no one caterpillar.

In this experiment, the activity of the active substance of example 120 is 100%.

Similar activity is exhibited by compounds of examples 52, 65, 78, 84, 85, 119, 123, 139, 141-144, 199 and 214.

Example G

Test on the pest Myzus

1 wt. part of the active substance of example 195 mixed with 7 wt. parts of dimethylformamide as solvent and 1 wt. part alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to a concentration of the active substance, equal to 0.1%.

Heavily infested peach aphid (Myzus persicae), cabbage leaves (Brassica oleracea) are treated by immersion in ready for use preparation of the active substance.

After the desired time determine the level of mortality. 100% means that died all aphids, and 0% means that the death of aphids were observed.

In this experiment, the activity of the active substance of example 195 is 95%. Similar activity is exhibited by compounds of examples 5, 8, 9, 10, 16, 18, 20, 39, 45 and 46.

Example 3

Test stunted growth giant is methylsulfoxide solvent.

Liquid agar obtained using peptone from the extract of malt, mixed with preparative form of the active substance in an amount to provide in each case the desired dosage of the active substance. After solidification thus obtained the nutrient medium is incubated at a temperature of 26oWith pieces of micelle extracted from colonies Coniophora puteana or Coriolus versicolor.

After conditioning at a temperature of 26oWith over three and, accordingly, seven days activity is determined by measuring the growth of hyphae and calculate the percentage of the degree of inhibition of growth in comparison with control untreated culture medium. 0% means that the growth of hyphae corresponds to an increase of the raw nutrient medium, and 100% means that the growth of hyphae stopped completely.

Active substances, their concentration of active substances and the results of the experiments are shown in table 6.

Example

Test protective effect against the pathogen Plasmopara (vine).

1 wt. part of the active substance of example 65 is mixed with 47 wt. parts of the mass of acetone as solvent and 3 wt. parts alkylsilanes ether polyglycol as intactos activity sprinkle young plants prepared by the preparation of the active substance, applied at the rate of 100 g/ha After drying the applied solution inoculant plants with an aqueous suspension of spores of mildew pathogen Plasmopara viticola and leave them for 1 day in an incubation box at a temperature of about 20oC and a relative humidity of 100%. After this plant set for five days in a greenhouse with a temperature of about 21oC and with a relative humidity of about 90%. Then plants moisturize and put on one day in the incubation box.

After 6 days after inoculation to assess the condition of plants in %. 0% means an activity that corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

In this experiment, the activity of the active substance of example 65 is 90%.

Example TO

Test protective effect against the pathogen Venturia (Apple).

1 wt. part of the active substance of example 214 mixed with 47 wt. parts of the mass of acetone as solvent specified quantities of solvent, add 3 wt. part alkylsilanes ether polyglycol as emulsifier and dilute the resulting concentrate with water to the desired concentration.

To be applied at a rate of flow, equal to 100 g/ha After drying the applied solution plants inoculant with an aqueous suspension of conidia of the pathogen of Apple scab Venturia inaequalis and leave them for 1 day in an incubation box at a temperature of about 20oC and a relative humidity of 100%.

The plants installed in the greenhouse with a temperature of about 21oC and with a relative humidity of about 90%.

12 days after inoculation to assess the condition of plants in %. 0% means an activity that corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

In this experience the potency of the compound of example 214 is 100%

All other compounds popadayuschie under the above-mentioned General formula (I) have similar fungicidal and insecticidal activity.

1. Carbanilide formula (I)

< / BR>
where a represents a residue of the formula

< / BR>
where R1means alkyl group with the number of carbon atoms one to four, halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five;

R2means a hydrogen atom, halogen, or a represents a residue of formula to four and the number of atoms of halogen from one to five,

or a represents a residue of the formula

< / BR>
where R4means halogenlampe with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

or a represents a residue of the formula

< / BR>
where R5means halogen atom, alkyl group with the number of carbon atoms one to four, halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

or a represents a residue of the formula

< / BR>
where R6means alkyl group with the number of carbon atoms one to four or halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five;

X is a sulfur atom, a group SO, SO2,

or a represents a residue of the formula

< / BR>
where R7means alkyl group with the number of carbon atoms one to four,

or a represents a residue of the formula

< / BR>
where R8means halogen atom or alkyl group with the number of carbon atoms one to four;

R9means a halogen atom or halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five,

Il is yireh or a group of the formula

< / BR>
< / BR>
where R10means alkyl group with the number of carbon atoms one to four,

or Q means a group of the formula

-*(CH2)n-Y-(CH2)p-

where Y represents an oxygen atom or a group S(O)rand r denotes the number 0, 1 or 2;

n and p independently of one another denote 0 or 1 and sign (*) in each case refers to the fraction of molecules that is connected to the phenyl residue of aniline fragment;

Z means a phenyl group, unsubstituted or mono-, disubstituted by identical or different halogen atoms, cyano, alkyl group with carbon atoms of from one to four alkyl fluoride group with the number of atoms from one to four and the number of fluorine atoms from one to five, or peredelnyj or pyrimidinyl residue, substituted by one or two chlorine atoms, fluorine, provided that the compound 2-methyl-N-(2-phenoxyphenyl)-5,6-dihydro-1,4-Ossetian-3-carboxamid excluded.

2. Means for controlling insects or pathogenic fungi, characterized in that it contains carbanilide formula (I):

< / BR>
where a represents a residue of the formula

< / BR>
where R1means alkyl group with the number of carbon atoms from one to odnogo to five;

R2means a hydrogen atom, halogen,

or a represents a residue of the formula

< / BR>
where R6means alkyl group with the number of carbon atoms one to four or halogenation group with the number of carbon atoms one to four and the number of atoms of halogen from one to five;

X is a sulfur atom,

or a represents a residue of the formula

< / BR>
where R8means alkyl group with the number of carbon atoms one to four;

R9means halogenating group with the number of carbon atoms one to four and the number of atoms of halogen from one to five;

Q means alkenylamine group with the number of carbon atoms from two to four, or a group of the formula

< / BR>
where R10means alkyl group with the number of carbon atoms one to four,

or Q means a group of the formula

-*(CH2)n-Y-(CH2)p-

where Y represents an oxygen atom or a group S(O)r, and r denotes the number 0;

n and p independently of one another denote 0 or 2 and the sign (*) in each case refers to the fraction of molecules that is connected to the phenyl residue of aniline fragment;

Z means a phenyl group, unsubstituted or mono-, tizamidine, alkyl fluoride group with the number of atoms from one to four and the number of fluorine atoms from one to five.

 

Same patents:

The invention relates to Amida aminodiphenylamine acid I in which R1, R2each independently of one another denotes N, And, moreover, one of the residues R1or R2in all cases has a value other than H; R1and R2together represent alkylene with 3-5 C-atoms, R3and R4each independently of one another denotes N or C1-C4-alkoxy; R3and R4together denote also-O-CH2-O - or-O-CH2-CH2-O-; And denotes alkyl with 1-6 C-atoms, R5means-X-Y, X represents CO, Y represents a phenyl or cyclohexyl, unsubstituted monosubstituted COOH or cooa, n denotes 1, 2 or 3, as well as their physiologically acceptable salts

The invention relates to new derivatives of 2- (iminomethyl) aminobenzoyl General formula (I) where a represents either a radical represented by the formula of the invention in which R1and R2denote, independently, a hydrogen atom, a group HE, a linear or branched alkyl or alkoxy having from 1 to 6 carbon atoms, R3means a hydrogen atom, a linear or branched alkyl with 1-6 carbon atoms or the radical COR4, R4means a linear or branched alkyl with 1-6 carbon atoms, or radicals represented by the formula of the invention, R5means a hydrogen atom, a group HE or linear or branched alkyl or alkoxy with 1-6 carbon atoms, means thienyl, X means Z1-, -Z1-CO-, -Z1-NR3-CO, -CH=CH-CO - or a simple bond, Y represents a radical chosen from the radicals Z2-Q, piperazinil, homopiperazine, -NR3-CO-Z2-Q-, -NR3-O-Z2-, -O-Z2Q-in which Q means a simple bond, -O-Z3and-N(R3)-Z3-, Z1, Z2and Z3means independently a simple link or a linear or branched alkylene with 1-6 carbon atoms, preferably Z1, Z2and Z3means -(CH2)m-, and m is an integer, R

The invention relates to a method for sulfonyl-isocyanates of the formula J-SO2NCO, where J means the J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-8, the interaction of phosgene and sulfonamida formula J-SO2NH2which is introduced into the reaction mixture containing the inert solvent, the catalyst and the phosgene and the reaction is carried out in the presence of molar excess of phosgene in relation with the sulfonamide

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The invention relates to compounds of the following formula 1, which inhibit the enzyme glycinamide ribonucleotide the formyl transferase (GARFT)

The invention relates to the field of organic chemistry

The invention relates to a method of stereoselective obtain enantiomer heterobicyclic alcohol

The invention relates to new heterocyclic condensed to benzoylpyridine General formula I, where R1and R2denote independently from each other H or A; X denotes CR4R5; C=Z or O, Y represents CR6R7Z denotes O or CH2, R4, R5, R6or R7denote independently from each other H, A, HE or OA, or R5and R6or R7and R8indicate link together, with each molecule may receive a maximum of only one such bond, or R4and R5indicate together O-(CH2)2-O or O-(CH2)3-O, or R8and R9denote independently from each other H or A; And denotes alkyl with 1 to 6 C-atoms; n represents 0 or 1, and their physiologically acceptable salts

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The invention relates to pyrazole derivative of the formula I, where1means the group - NRR1R2or group-OR2, g2- g6the same or different and independently of one another denote hydrogen, halogen, C1-4alkyl, C1-4alkoxyl, trifluoromethyl, or C1-4allylthiourea; w2-w6the same or different and independently of one another denote hydrogen, halogen, C1-4alkyl, C1-4alkoxy or trifluoromethyl, provided that at least one of the substituents g2-g6and one of the substituents w2-w6different from hydrogen; R1means hydrogen or C1-4alkyl; R2- nah3-15-carbocyclic radical, unsubstituted or mono - or multiply substituted WITH1-4by alkyl; R3is hydrogen or the group CH2-R6; R4and R5each independently of one another denote hydrogen or C1-4alkyl; or R4means hydrogen and R5and w6together form an ethylene radical; R6means hydrogen, or when the deputies of the g2g3, g4, g5and/or g6different from1-4of alkyl, R6means hydrogen, C1-4alkyl or C1-5alkoxyl, and their salts
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