JPS62185065A - N-(4-(haloalkoxy)trifluoromethylphenyl)-n'-benzoylurea, manufacture and vermicidal use - 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 [Industrial Application Field] The present invention provides a novel substituted N-(4-(haloalkoxy)trifluoromethylphenyl)N/-benzoyl urea,
It relates to its production method and its use for pest control.

[Prior art, problems to be solved by the invention, and means for solving the problems]

The compounds of the present invention have the following formula: [wherein B is 1 carbon atom having 1 to 9 halogen atoms]
represents a haloalkyl group of 4 to 4, R1 is a hydrogen atom,
represents a halogen atom, methyl group, ethyl group, methoxy group or ethoxy group, 8 represents a halogen atom or a methoxy group, 几3 represents a halogen atom or a trifluoromethyl group, and R4 and Rs are each independently represents a hydrogen atom, a halogen atom, or a trifluoromethyl group, provided that at least one of R3, R4 and Rs represents a trifluoromethyl group, and R4 and Rs cannot represent a hydrogen atom at the same time.

Within the scope of the invention, halogen atoms are to be understood as representing fluorine, chlorine and bromine atoms, with preference given to using fluorine and chlorine atoms.

Preferred formula in terms of pest control activity! A compound represented by the formula, in which R1 represents an alkyl group having 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms, or a carbon atom substituted with 1 to 9 halogen atoms It is a compound representing an alkyl group of number 2 to 4.

Particularly favorable formula! The compound represented by the following formula is a compound in which R3 represents a chlorine atom or a trifluoromethyl group, and R4 and S each independently represent a hydrogen atom, a chlorine atom, or a trifluoromethyl group; hydrogen atom,
A compound representing a fluorine atom or a chlorine atom, in which R represents a fluorine atom or a chlorine atom; and in the formula, R1 and R
, independently of each other represent a fluorine atom or a chlorine atom, or both represent a fluorine atom at the same time.

%lC! The compounds represented by the formula I are as follows:
CHF, group, -CF3 group, -CF, C1 (F, group, -C
[(.

-CF, group, -CF, CF, group, -OF, CHFC
j group, -CF, CHCj! group, -〇F, CC13 group,
-CF2CHBr2 group, -CF, CHFB r group, -
CF, CHBr2 group, -CH1CHBrCH2Br group or -CF2CHFCF3 group, preferably 10F, C[-
1F.

-CF2CHFCl group, -CF2CHFBr group or -CF2Cf (FCF, groups selected from the group consisting of -CF2CHFCl group, -CF2CHFBr group or -CF2Cf (FCF, groups), and especially compounds in which R is a group -CF, CHFC
It is a compound representing F.

Compounds of the formula I can be prepared by known methods (for example as described in German Offenlegungsschrift No. 2123).
236 and 2601780 and EP 13414).

Thus, for example, a compound of formula l can be prepared by a) reacting a compound of formula Il: AI+5 with a compound of formula m: or b) reacting a compound of formula I: LS with a compound of formula m: (2): It can be produced by reacting with a compound represented by R1 2 or by reacting a compound represented by the above formula... with a compound represented by the following formula V1: Yajima.

In the above formulas n, in, iv, v and Vl, it is replaced with fig.

几□, R,, R3, R1, and BS have the same meaning as defined in formula 1+11t-, and R6 is an unsubstituted C1-C8 alkyl group or a halogen substituted, preferably a chlorine substituted represents an alkyl group having 1 to 8 carbon atoms.

The above steps a) to C) can preferably be carried out under normal pressure and in the presence of an organic solvent or diluent. Examples of suitable solvents or diluents are ethers and ethereal compounds such as diethyl ether, dipropyl ether,
Cyphthyl 2-thyl, dioxane, dimethoxyethane and tetrahydro7rane; N,N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons X, 4I
K-benzene, toluene, xylene, chlorofocum, methylene chloride, carbon tetrachloride and chlorobenzene; nitriles such as acetonitrile or propionitrile; dimethyl sulfoxide; and ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone. Step a) is usually carried out within a temperature range of -1
0″ to +100°C, preferably 15＠ to 25°C
, optionally in the presence of an organic base, such as triethylamine.

During the process, the temperature range is 0 to 150°C, preferably at the boiling point of the solvent used and, if desired, in the presence of an organic base such as pyridine and/or an alkali metal or alkaline earth metal, preferably sodium It is carried out by adding. For the reaction of the urethane 2) according to step C), a temperature range from about 60° C. to the boiling point of the reaction mixture is preferred, and the solvents used are toluene,
Aromatic hydrocarbons such as xylene, chlorobenzene, etc. are preferred.

The starting materials of the formulas n, m, tv, v and 2 are known and, if new, can likewise be prepared by known methods. Substituted anilines of the formula ■ are new compounds, which likewise constitute an object of the present invention, and which can be prepared by methods known in the literature, such as those described in the Journal of the American Chemical Society 4 (J, Am, Chem, 8oc).
, ) can be prepared by etherification of a suitable substituted 4-acetaminophenol with hexafluoropropylene according to the method described in Volume 73 (1951), page 5831. continue,
The N-acetyl group is removed from the obtained 4-acetamino(haloalkyl)phenyl ether to obtain aniline represented by formula (2). A specific substituted aniline represented by the formula ■ in which R3 represents a halogen atom is an aniline represented by the following formula ■: F3 [wherein R represents the same meaning as defined above]. It can also be obtained by direct halogenation [synthesis (8ynthes
is), Vol. 1985, p. 669].

Insecticidal N in which the 3rd or 4th position of the phenyl nucleus is substituted with a haloalkoxy group and optionally a cyclochlorine atom or a CF3 group
-Phenyl-N'-(2-chloro-6-fluorobenzoyl)urea is described in DE-A-2801316.

Insecticides with a similar structure having a N-a-no\loalkoxyphenyl group attached to the 3-position with a CF3 group are disclosed in European Patent Application No. 23884. Compared to these prior art compounds, the essential features of the 4-haloalkoxyphenylbenzoyl urea of the present invention are that the 7-enyl nucleus is substituted by a CF3 group and further substituted in the 3- and/or 5-position. It consists in having a group.

Surprisingly, the compounds encompassed by formula 1 of the present invention are
It has been found that it exhibits excellent properties as a pest control agent, with favorable plant tolerance and low toxicity in warm-blooded animals. These compounds are especially suitable for controlling insects and mites which are harmful to plants and animals.

In particular, the compound represented by formula 1 is applicable to the following insect species, Lepidoptera and Coleoptera.
Ptera), Homoptera ()iomoptera),
Heteroptera, Hymenoptera
ptera), Thysanoptera (Thysanoptera)
ra), Orthoptera, Anoplura, Siphonapt.
era), Mallo-phaga
), Thysanura, Termitales (
Isoptera), Psocoptera
e-ra), and Hymenoptera (Hymenoptera)
) and typical species belonging to the order Acarina.

The good pesticidal activity of the compounds of formula 1 of the present invention is characterized by a mortality rate of at least 50-60% of the above pests (
mortality rate).

In addition, the compound represented by formula 1 may be, for example, Iepaz (
In addition to being effective against flies and mosquito larvae such as Musca domesticus, it is effective against insects that damage plants by feeding on ornamental and useful plants, especially in cotton cultivation [e.g. Spodoptera littoralis (Spodoptera L.
ittoralis) and heliotis v4 shi7
Cephus()ieliothi's wires -c
ens)) and insects that cause feeding damage in fruit and vegetable cultivation [
For example, Las-peyresia bomonella (Las-peyresia bomonella)
sia pomonel la), Leptinotarsa decem
li-neata) and Epilachna varivestis]. The compounds of formula 1 also exhibit excellent ovicidal and larvicidal activity against insects, especially the larvae of damaging insects. When compound No. 2 is ingested with food by insects in their adult stages, many insects, especially Anthonomus grandis,
In beetles such as P. ndis ), it causes reduced egg production and/or reduced hatching rates.

The compounds of formula I may further be used to protect ectoparasites such as Lucilia sericata (Lucilia 5eri-cat).
a)' and for the control of mites on livestock and useful animals, for example by treating animal bodies, cow sheds, barns, stables, etc., and pastures.

The activity of the compounds of formula 1 and compositions containing them can be substantially extended and adapted to the given environment by the addition of other insecticides and/or acaricides. Examples of suitable additives are organophosphorus compounds, nitrophenol and their derivatives, formamidine, urea, carbamates, pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis.
ngiensi's) formulations.

The compounds of the formula I are used in neat form or preferably together with the auxiliaries customary in formulation technology and can therefore be prepared in known manner as emulsion stock solutions, directly sprayable or dilutable solutions, diluted emulsions, aqueous preparations. , in aqueous solutions, powders, granules, and encapsulates, for example with polymeric substances. The method of application, such as spraying, dusting, scattering, scattering or pouring, as well as the nature of the composition, will be chosen depending on the intended audience and the environment of use.

The formulation, i.e. the composition or formulation containing the compound of formula 1 (active principle) or its combination with other insecticides or acaricides and, where appropriate, solid or liquid auxiliaries, can be prepared by known methods. For example, they are prepared by homogeneously mixing and/or milling the active ingredient with a solvent, a solid carrier and, if appropriate, extenders such as surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably moieties having 8 to 12 carbon atoms, such as xylene mixtures or substituted naphthalenes; phthalates such as diptylphthalate or dioctyl phthalate; cyclohexane or paraffins. aliphatic hydrocarbons: alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether; ketones, such as cyclohexanone: N-methyl-2-pyrrolidone,
Strong polar solvents such as dimethyl sulfoxide or dimethyl formamide; and epoxidized vegetable oils such as epoxidized coconut oil or soybean oil: or water.

Solid carriers which can be used, for example in powders and dispersible powders, are usually natural mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. It is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers to improve the physical properties. Suitable granulated absorbent carriers are of the porous type, for example pumice, crushed brick, seviolite or bentonite; and suitable non-absorbent carriers are materials such as calcite or sand. Furthermore, a large number of pre-granulated mineral and organic materials can be used, especially dolomite or granulated plant debris.

Depending on the nature of the compound of formula I or the combination thereof with other insecticides or acaricides to be formulated, suitable surface-active compounds include non-ionic, cationic and cationic compounds with good emulsification ratios, dispersibility and wetting properties. /or anionic surfactant.

It is to be understood that the term "1 surfactant" also includes mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surfactant compounds.

Suitable soaps are alkali metal salts, alkaline earth metal salts, or unsubstituted or substituted ammonium salts of higher fatty acids (Cto-Cta), such as oleic acid or stearic acid,
Or the sodium or potassium salts of natural fatty acid mixtures obtained, for example, from coconut oil or tallow. Additionally, fatty acid methyltaurate salts and inflected and unmodified phospholipids can also be used as suitable surfactants.

However, so-called synthetic surfactants, in particular difatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates, are also used in fJ4g.

The fatty sulfonates or sulfates contain an alkyl group of 8 to 22 carbon atoms, usually in the form of an alkali metal salt, an alkaline earth metal salt or an unsubstituted or substituted ammonium salt, and also include the alkyl part of an acyl group;
For example, sodium or calcium salts of lignosulfonic acid, dodecyl sulfate or mixtures of fatty alcohol sulfates obtained from natural fatty acids. These compounds also include salts of sulfuric esters and sulfonated polyadducts of fatty alcohols and ethylene oxide. The sulfonated benzimidazole derivatives preferably contain two sulfonic acid groups and one fatty acid group containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcicum or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensation products. p- containing the corresponding phosphate, e.g. 4 to 14 moles of ethylene oxide
Salts of phosphoric esters of nonylphenol adducts are also suitable.

The nonionic surfactant is preferably an aliphatic or cycloaliphatic alcohol, or a polyglycol ether derivative of a saturated or unsaturated fatty acid and an alkylphenol, which has 3 to 30 glycol ether groups, (aliphatic ) Further suitable nonionic surfactants containing 8 to 20 carbon atoms in the hydrocarbon portion and 6 to 18 carbon atoms in the alkyl portion of the alkylphenol are polyethylene oxide and polypropylene glycol, Ethylene diamine polypropylene is a water-soluble adduct with glycol and alkyl polypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, the adduct containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene These compounds containing glycol ether groups usually contain from 1 to 5 ethylene glycol units per propylene glycol unit.

Typical examples of nonionic surfactants are nonylphenol-polyethoxyethanol and castor oil polyglycol.
Ether, polypropylene/polyethylene oxide adduct, tripterphenoxybolyethoxyethanol,
Polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan and polyoxyethylene sorbitan trioleate are also suitable nonionic surfactants.

The cationic surfactants preferably contain as N-substituent at least one C8-C22 alkyl group and as other substituents lower unsubstituted or halogenated lower alkyl, benzyl or lower hydroxyalkyl groups. It is a quaternary ammonium salt containing. The salt is preferably in the form of a halide, methyl sulfate or ethyl sulfate, such as stearyltrimethylammonicum chloride or benzyl di(2-chloroethyl)ethylammonicum promitote.

Surfactants customary in the pharmaceutical industry are described, for example, in the following publications: @McCutchan's Detergents and Emulsifiers Anis 7A/ (MCC
Utcheons Deter-gents and
Emulsifiers Annual)”, ?
Tsuku Publishers, Ringwood, New Chassis, 19
1979; Helmut Stallahier (Helmut 8
tache), @Ten5id Ta5henbuch”, 2nd edition, Carl Hansafel
ser Verlag), Munich and Queen.

1981.

Pest control compositions usually contain a compound of formula I or a mixture of said compound with other insecticides or acaricides.
%, preferably (Ll to 95eIb, solid or liquid auxiliary 1 to 99.9%.

and 25% of a surfactant, preferably α1 to 20-.

Although commercial products are preferably formulated as concentrates, consumers typically use dilute formulations with substantially lower concentrations.

The compositions may also contain other ingredients, such as stabilizers, defoamers, viscosity regulators, binders, tackifiers and fertilizers, or other active ingredients for obtaining special effects.

[Examples and effects of the invention]

3.3-hexafluoropropoxy)-S-2-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)-5-()lifluoromethyl)acetaminobenzene 29.6tf , salt production @100mt and ethanol 4
The mixture is refluxed for 17 hours in a mixture with 0.00 Coffin, then the solvent is distilled off, the residue is made alkaline with 10% sodium hydroxide solution and then extracted with ether. The ethereal extract was dried over sodium sulfate and the solvent was then removed by evaporation under vacuum. The title compound is obtained as.

3-trifluoromethyl-4-(1,1,2°S,S,
Add S-hexafluoropropoxy)anis/1st in acetonitrile somt and then add N-chlorosuccinimide &7f in portions to this mixture at 60°C. Once the exothermic reaction has subsided, the batch is refluxed for 2 hours. , then the solvent is removed by vacuum distillation. The remainder was poured into methylene chloride, and this solution was added twice with 50 ml of 10 ml of sodium hydroxide solution.

It is then washed with sodium chloride solution and dried over sodium sulfate. The solvent was removed by evaporation and the liquid residue was then chromatographed on silica gel (eluent: 4:1 mixture of hexane/ethyl acetate) and 2-chloro-4-(1,1,2,5,S , 5-hexafluoropropoxy)-57-)lifluoro-methylaniline (
boiling point 281°-83°C 74 x 10-2) and about twice the amount of 2-chloro-3-trifluoromethyl-4
-(1,1,2,3,3°3-hexafluoropropoxy)aniline (ip=14340) is obtained as a colorless oil.

The formula obtained by the above method! The metal compounds represented by are summarized in Table K below.

The following compounds of the formula (3) in which %Rs, R4, Rs and R have the meanings given in the table below can also be obtained by the above method.

Chi R41'L, R CI CI -CF, -CF,
-COP-CF3Br H-CF3-CF, -CH
F-CF3-CF, CI CI
-CF, -CHF.

Cl-CF3Cl -CF, -C) ICI.

CI-CF'3H-CFz-CHFB
rBr C1-CF, -CF, -CB
Y@-OF, HBr -σ, -C)IF
-OF.

-OF, CI C1-CF, -CHF-
CFs-σ@CI Br-(
3”!-COP-CF.

Br-CFI)l-CF
I-CHF-CF3C1-CF, CI
-σ, -CHF-CF.

-CF, H-σ, -σ, -a-positive-σ.

Example 2 Ni-4-(hexafluoropropoquine)phenyl Example 1
2-chloro-4-' (1゜1.2,5,5
．． 5-hexafluoropropoxy)-5-()lifluoromethyl)aniline 50f dried diethyl ether 10
Add to research. While stirring, 1.57 g of 2,6-cyfluorobenzoyl isocyanate) is added dropwise. 2 hours later,
The crystalline precipitate is isolated by passing through and then washed with a small amount of ether to give white crystals of the title compound (compound 1) of the formula: mp 158@-159 DEG C.

The following compounds of formula I are also prepared using the above method.

The following compound represented by formula 1 can also be obtained by the above method.

Example 3: t Wettable powder a) b) c) Compound or mixture of formula 1 25% 50%
75 Sodium gutsulfonate 5%
5% -2 sodium uryl sulfate 5
% -5% Highly dispersed silicic acid 5% 10%
10% power Orin
62chi 27% - Irrigation agent which can be diluted with water to obtain a suspension of the desired concentration by thoroughly mixing the active ingredient or mixture with the auxiliaries and then thoroughly grinding the mixture in a suitable mill. is obtained.

2 Compound or mixture of emulsion stock solution 2 T 10
% Calcium Dodecylbenzenesulfonate
3cyclohexanone 30% xylene mixture 509G By diluting this emulsion stock solution with water, an emulsion of the desired concentration can be obtained.

Five powders 1) b) Compound or mixture of formula I 5%
8% mail
95 Chi - Kaolin
92 active ingredient is mixed with the carrier and this mixture is mixed in a suitable mill! By crushing, a powder that could be used as it was was obtained.

4. Extruded granules Compound or mixture of formula I 10-Sodium lignosulfonate
2-carboxymethylcellulose
1 chica orin
87 - Mixing and milling the active ingredient or mixture with auxiliaries and subsequently moistening the mixture with water.

The mixture is extruded and dried in a stream of air.

Compound of formula I 3% polyethylene glycol (mot, wt, 200)! Chika Orin
The 94% finely ground active ingredient or mixture is applied homogeneously to the polyethylene glycol-moistened kaolin in a mixer. This method uses non-powder! 1 injection-coated granules are obtained.

& suspension stock compound or mixture of formula 1 40%
ethylene glycol 10
% Sodium Lignosulfonate 1
oz carboxymethyl cellulose
1.57% formaldehyde bath solution
α2-75% aqueous emulsion type silicone oil
α8chi water
By homogeneously mixing the finely ground active ingredient or mixture together with auxiliary agents and diluting with water, a suspension ratio-thickness is obtained which makes it possible to obtain an M suspension of the desired concentration.

Example 4: Musca domestica
Effect on freshly prepared nutrie substrates (nutrie
Divide 50 t into each numbered beaker. A predetermined amount of 1% A7Tone solution of each test compound is added dropwise to the nutrient substrate in a beaker to obtain 400 pp” of active ingredient #&.The substrate is then mixed thoroughly and then acetone is added to the nutrient substrate in a beaker. Leave to evaporate for 20 hours.

Thereafter, 25 1-day-old houseflies were treated with the nutritional base i for the test, each with the active ingredient at a given concentration.
t-containing individual beakers. After the spiderlings have coaxed, the pupae are separated from the substrate by flushing with water and then placed in a container closed at the top with a loose lid.

The flushed pupae of each batch are counted to determine the efficacy of the test compound on pupal growth. After 10 days, count the number of flies that hatched from the pupae.

The compound of formula 1 according to Example 2 showed good activity in this test.

1 mA of a water bath solution containing I15%'i of the test compound is added to 9 ml of culture medium at 50°C. Approximately 50 hatched Lucilia sericata were then added to the culture medium, and the insecticidal effect was determined by evaluating the mortality rate.
Measure after 8 and 961#.

In this test, the compound of formula I according to Example 2 shows good activity against Lucilia sericata.

Example 6: Aedes aegy
pti ) 400 ppm of (I (Aedes aegyp
ti) Place 30 to 40 animals in a beaker containing the test compound. Mortality is determined after 2 and 7 days.

In this test, the compound of formula I according to Example 2 showed good activity against the Egyptian Yaps mosquito.

Potted cotton plants approximately 25 c1n in height are sprayed with an aqueous emulsion containing the individual test compounds at concentrations of 31 (175 and 50 ppm). After the spray coating has dried, the cotton plants are exposed to % one stage Subodoptera. Rifdraris (8p
odoptera Litto-ralis) and Heliotis viretscens (Helitto-ralis)
parasitize the larvae of C. rescens). The exam is 24
℃ and 60% relative humidity. The mortality rate (ch) of the test pests is measured after 2 days.

In this trial, compound 14 was tested against Spodobutella and Heliotis, respectively (L 75 ppm and 8 ppm at 50 ppm).
It shows a mortality rate of 0-100.

Example 8: Effect on Three cotton plants, each about 15-20 cm tall and grown in containers, are treated with a sprayable liquid formulation of the test compound at a yield of 400 ppm.

After the spray coating has dried, the potted plants are placed in a metal container with a volume of 20 t and covered with a glass plate.

The humidity inside the container is adjusted so that no water condenses. Avoid direct contact with the plants.0 then 3 plants: a) 50 larvae of Subodoptera 2 lyfdraris or Heliothis virescens at stage I4, b) larvae of Subodoptera lyfdraris or Heliotis virescens at stage L3. 20 eggs, C) 2 deposits of eggs of Spodoptera rifdraris or Heliothis virescens.

(The procedure is to place two leaves of each plant in a Plexiglas cylinder with both ends closed with muslin. Subodopte 2
Add two deposits of eggs of Heliothis, or a portion of a cotton leaf on which eggs of Heliothis are deposited, to the leaf sealed in its cylinder. ) Evaluations relative to untreated controls were made after 4 to 5 days and used the scale described below.

a) Number of larvae still alive; b) prevention of larval development and molting; C) Feeding damage (breakage and perforation damage), d) Rate of hatching (number of larvae hatched from eggs).

In this test, the compound of formula I of Example 2 shows good activity against all.

Working Example 1 Eggs of Subodobutella rifudularis deposited on a paper are cut into pieces and then immersed in a 105% by weight solution of each test compound in a 1:1 mixture of acetone and water. The treated pile is then removed from this mixture and kept in a plastic dish at 28° C. and 60% humidity. The colony rate, ie the number of larvae developed from treated eggs, was determined after 5 days.

The compound of formula I of Example 2 is highly effective in this test.

! 20% by weight of test compound, 70% by weight of xylene and 10% by weight of a mixture of adducts of alkylphenols with ethylene oxide and calcium dodecylbenzenesulfonate.
A mixture consisting of: An aqueous emulsion containing 800 ppm of the test compound is prepared from this concentrate. 7 new Phaseolus vulgaris
2 shrimps accumulated on the leaves of the Mexican bean beetle (Mexican bean b.
Approximately 100 eggs of C. eetle) are moistened with the above aqueous emulsion (concentration=8aOppn) and then dried under light. The treated eggs are kept in a ventilated container until the untreated controls piled up at the same time are evaluated.

Assess lethality under a stereomicroscope.

The compound of formula 1 in Example 2 is very effective in this test.

A corresponding amount of hydrating powder containing 25% by weight of the test substance was added to 8% by weight.
Mix with sufficient water to produce an aqueous emulsion with 0.00 ppm of active ingredient 111E.

Deposits of eggs of Heliothis for one day on cellophane and eggs of Leptinotarsa on potato leaves are soaked in these emulsions for 5 minutes and then collected by suction on circular filter paper. . Place the treated eggs in a Petri dish and leave in the dark.

The detailing rate is determined after 6 to 8 days compared to the untreated later.

The compound of formula 1 in Example 2 is very effective in this test.

Eggs of Cuspeiresia Pomonella that have not been older than 24 hours are immersed on filter paper for 1 minute in a water-to-water solution containing the test compound @ 400 ppm f.

After the solution has dried, place the eggs in a Petri dish.

Leave at a temperature of 28°C. The percentage of larvae scored from treated eggs is evaluated after 6 days.

The compound of formula I of Example 2 shows good activity in this test.

! Two cotton plants at the 6-leaf stage are each sprayed with an aqueous emulsion formulation containing 400 ppm of the test compound.

After the sprayed coating has dried (approximately t5 hours), each plant is infested with 10 adult beetles (Anthonomus grandis). A plastic cylinder capped with gauze is then placed over the treated plants infested with the test insects to prevent the beetles from migrating from the plants. Thereafter, the treated plants are kept at 25° C. and a relative temperature of about 60%.

The evaluation is carried out after 2, 5.4 and 5 days by determining the mortality of the beetles (percentage in dorsal position) and the phagocytosis compared to the untreated ones.

Note) and Tetranychus cinnabarinus (Tetra-
16 hours before the test for acaricidal action, Paseo/l/
Phaseolus vulga
Tetranychus urticae ((
JP-susceptibility ratio) and Tetranychus cinnabarinus (u
Infection is carried out using leaf pieces infected with a culture of p-it (resistant to diazinon). The treated infected seeds are sprayed with a test solution containing 400 ppm of the compound to be tested until dripping. Counting of the number of live and dead adults and larvae (all in mobile stage) is carried out after 24 hours and again after 7 days under the stereomicroscope. One plant is used for each test substance and test species.

While conducting the test, the plants are kept in a temperature compartment of 25°C.

In this test, the compound of formula 1 of Example 2 is highly effective against Nato2nyx curticae and Nato2nyx cinnabariwaum.

Example 15: Anthonomas grandis 24 after detailing
Adults of Anthonomus grandis that have not passed the age are transferred in groups of 25 to empty cages.

The cage is then immersed in an acetone ratio solution containing 800 pprn of the test compound for 5 to 10 seconds; after the beetles are dry, place them in a dish with a lidded bait;
Approximately 2.3 degrees per week during mating and spawning.

The eggs are flushed out with water, counted and sterilized by placing them in a disinfected aqueous solution for 2-3 hours, then placed in a dish containing suitable larval food; after 7 days, the larvae are Count the eggs to determine if they hatched.

The effectiveness of the test compound in preventing sustained reproduction is determined by observing egg deposits over a period of about 4 weeks. Evaluation is done by measuring the reduction in the number of eggs deposited and larvae evaluated compared to untreated controls.

Example 20 Compounds of formula I are highly effective in this test.

Potted Chinese cabbage plant in four-leaf stage (pot size: 1 diameter
0 cm) with an aqueous emulsion containing the test compound at a concentration of l 75 ppm and the plants are dried.

After 2 days, each treated Chinese cabbage plant had 10 Plutella xylostella (Plutella xylostella) at the growing stage.
axylostella) t-parasitize. The test is carried out in dim light at 24° C. and 60° relative humidity. Evaluation of mortality rate vb) is carried out after 2 and 5 days.

Compound 14 of Example 2 was 80-100-
This shows the mortality rate (death rate).

(2 others)

Claims (26)

[Claims] (1) The following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is 1 carbon atom having 1 to 9 halogen atoms
-4 represents a haloalkyl group, R_1 represents a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group, or an ethoxy group, R_2 represents a halogen atom or a methoxy group, and R_3 represents a halogen atom or a trifluoromethyl group. and R_4 and R_5 independently represent a hydrogen atom, a halogen atom or a trifluoromethyl group, provided that R_3,
At least one of R_4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time. (2) A compound according to claim 1, wherein in formula I, R represents an alkyl group having 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms. (3) A compound according to claim 1, wherein in formula I, R represents an alkyl group having 2 to 4 carbon atoms substituted with 1 to 9 halogen atoms. (4) Claims 1 to 3 in which R_3 represents a chlorine atom or a trifluoromethyl group, and R_4 and R_5 each independently represent a hydrogen atom, a chlorine atom, or a trifluoromethyl group. A compound according to any one of the following items. (5) In formula I, R_1 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and R_2 represents a fluorine atom or a chlorine atom, according to any one of claims 1 to 4. Compound. (6) The compound according to claim 5, wherein in formula I, R_1 and R_2 each independently represent a fluorine atom or a chlorine atom. (7) The compound according to claim 6, wherein in formula I, both R_1 and R_2 simultaneously represent a fluorine atom. (8) In formula I, R is -CHF_2 group, -CF_3 group,
-CF_2CHF_3 groups, -CH_2-CF_3 groups, -
CF_2CHFCl group, -CF_2CHCl_2 group, -
CF_3CCl_3 groups, -CF_2CHBr_2 groups, -
CF_2CF_3 group, -CF_2CHFBr group, -CF
_2CHBr_2 groups, -CH_2CHBrCH_2Br
8. A compound according to claims 1 to 7, which represents a group selected from the group consisting of -CF_2CHFCF_3 and -CF_2CHFCF_3. (9) In formula I, R is -CF_2CHF_2 group, -CF
_2CHFCl group, -CF_2CHFBr group and -CF
9. A compound according to claim 8, which represents a group selected from the group consisting of _2CHFCF_3 groups. (10) In formula I, R_3 is -CF_2CHFCF_3
A compound according to claim 8, which represents a group. (11) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (12) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (13) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 9, which is represented by: (14) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (15) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (16) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (17) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (18) The following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The compound according to claim 10, which is represented by: (19)a) React the compound represented by the following formula II: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) with the compound represented by the following formula III: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) or b) the compound represented by the following formula IV: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV) and the compound represented by the following formula V: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) or c) reacting the compound represented by the above formula II with the compound represented by the following formula VI: ▲ Numerical formula, chemical formula, table, etc.
In II to VI, substituents R, R_1, R_2, R_3, R
_4 and R_5 have the same meanings as defined in Formula I below, and R_6 represents an unsubstituted C1-C8 alkyl group or a halogen-substituted C1-C8 alkyl group] The following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R represents a haloalkyl group having 1 to 4 carbon atoms and having 1 to 9 halogen atoms, and R_1 is a hydrogen atom or a halogen atom. , represents a methyl group, ethyl group, methoxy group or ethoxy group, R_2 represents a halogen atom or a methoxy group, R_3 represents a halogen atom or a trifluoromethyl group, and R_4 and R_5 each independently represent a hydrogen atom, a halogen atom, represents an atom or a trifluoromethyl group, provided that R_3,
At least one of R_4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time. (20) Following formula II: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) [In the formula, R is 1 carbon atom having 1 to 9 halogen atoms
-4 represents a haloalkyl group, R_3 represents a halogen atom or a trifluoromethyl group, and R_4 and R_5 each independently represent a hydrogen atom, a halogen atom or a trifluoromethyl group, provided that R_3,
At least one of R_4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time. (21) The following formula IV: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) [In the formula, R is 1 carbon atom having 1 to 9 halogen atoms
-4 represents a haloalkyl group, R_3 represents a halogen atom or a trifluoromethyl group, and R_4 and R_5 each independently represent a hydrogen atom, a halogen atom or a trifluoromethyl group, R_3, R_
At least one of 4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time. (22) With suitable carriers and/or other auxiliaries, the following formula
I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is 1 carbon atom with 1 to 9 halogen atoms.
-4 represents a haloalkyl group, R_1 represents a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group, or an ethoxy group, R_2 represents a halogen atom or a methoxy group, and R_3 represents a halogen atom or a trifluoromethyl group. and R_4 and R_5 independently represent a hydrogen atom, a halogen atom or a trifluoromethyl group, provided that R_3,
At least one of R_4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time. (23) The following formula I for controlling typical insects and acarids: ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is carbon having 1 to 9 halogen atoms. Number of atoms: 1
-4 represents a haloalkyl group, R_1 represents a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group, or an ethoxy group, R_2 represents a halogen atom or a methoxy group, and R_3 represents a halogen atom or a trifluoromethyl group. and R_4 and R_5 independently represent a hydrogen atom, a halogen atom or a trifluoromethyl group, provided that R_3,
At least one of R_4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time. (24) The method according to claim 23 for controlling insects that damage plants in their larval stage. (25) The method according to claim 24 for controlling harmful organisms on cotton. (26) The following formula I: ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is 1 carbon atom having 1 to 9 halogen atoms
-4 represents a haloalkyl group, R_1 represents a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a methoxy group, or an ethoxy group, R_2 represents a halogen atom or a methoxy group, and R_3 represents a halogen atom or a trifluoromethyl group. and R_4 and R_5 independently represent a hydrogen atom, a halogen atom or a trifluoromethyl group, provided that R_3,
At least one of R_4 and R_5 represents a trifluoromethyl group, and R_4 and R_5 cannot represent a hydrogen atom at the same time], or an effective amount of the compound as a pest control agent; Insects and pests, consisting of treating or contacting pests, their various stages of development or their habitat, with a composition comprising a pest control agent in an effective amount together with auxiliaries and suitable carriers therefor. How to control typical acarids.