JP2000281648A - Insecticidal azine derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new compound exhibiting a stronger insectcidal activity than ever, having characteristics of not harming profitable insects, environment, etc., and useful as an insecticide of low toxicity, when the compound is used for exterminating pests in a paddy field, an orchard, etc., or in an environmental sanitation aspect. SOLUTION: A compound of formula I [R1 is a (substituted)phenyl; R2 is a (substituted)phenyl; R3 is H, a halogen, a 1-4C (halo)alkyl or the like, or two adjacent R3s may collaboratively form a 5 to 7-membered ring; A is CHR3, S, O or the like; B is CHR3-O, CR3=N or the like], for example, [4-[[[(pyrid-2- ylmethylene)azamethylene]azamethylene]4-chlorophyenyl) methyl]phenyl]methylthiomethane. The compound of formula I can be, for example, produced by a method of reacting (A) an aldehyde compound of formula II with (B) a hydrazone compound of formula III in an amount of, preferably, 0.5-2 mol per mol of the component A, more preferably, 0.8-1.2 mol per mol.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel azine derivative or an agriculturally acceptable salt thereof and its use as an insecticidal composition.

[0002]

2. Description of the Related Art JP-A-9-3038,
JP-A-278744 and JP-A-10-7637 describe that 4-substituted-4'-alkylthioalkylbenzophenoneazine derivatives exhibit insecticidal activity.

[0003]

[Problems to be solved by the invention] Paddy fields, fields, orchards,
In the pest control scene in the forest or environmental sanitation scene,
There is a need for a compound that has stronger insecticidal activity and properties that do not harm the beneficial insects and the environment, and that has low toxicity. Therefore, the present inventors have made intensive studies for many years to develop excellent insecticides.

[0004]

As a result, the following general formula (1) having excellent insecticidal activity:

[0005]

Embedded image(Where R¹Is a halogen atom, C₁-C₄Alkyl group,
Halo C₁-C₄Alkyl group, C₁-C₄Alkoxy group or
Is Halo C₁-C₄Even when substituted with an alkoxy group, etc.
A good phenyl group,²Is C₁-C₄Alkylthio
C₁-C₄Alkyl group, C₁-C₄Alkylsulfini
Le C₁-C₄Alkyl group, C₁-C₄Alkylsulfoni
Le C₁-C₄Alkyl group, C₁-C₄Haloalkylthio
C₁-C₄Alkyl group, C₁-C₄Haloalkyl sulf
Inil C₁-C₄Alkyl group or C ₁-C₄Haloalk
Rusulfonyl C₁-C₄Has an alkyl group as a substituent
A is -CHR³-O-, -CR³
= N-, -CR³= CR³-, -CHR³-, -S-,
-O- or -NR⁴And B is -CHR³-O-,
-CHR³-CHR³-, -CR³= CR³-, -CR
³= N- or -NR⁴-And R³Are each independently water
Elemental atom, halogen atom, C₁-C₄Alkyl group, halo C
₁-C₄Alkyl group, C₁-C₄Alkoxy group, halo C
₁-C₄Two alkoxy groups or adjacent
R³May together form a 5- to 7-membered ring,⁴Is
Hydrogen atom or C₁-C₄Is an alkyl group)
The discovery of a new azine derivative led to the completion of the invention
Was.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1), examples of the halogen atom include a fluorine, chlorine, bromine or iodine atom, and examples of the C ₁ -C ₄ alkyl group include methyl,
Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl group and the like. Examples of the C ₁ -C ₄ alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n -Butoxy, isobutoxy, sec-butoxy or tert-butoxy group. Examples of the C ₁ -C ₄ haloalkyl group include 1- or 2-chloroethyl, chloromethyl, dichloromethyl, bromomethyl, 1- or 2-bromoethyl. , Fluoromethyl,
Difluoromethyl, 1-or 2-fluoroethyl or trifluoromethyl _group. Examples of C 1 -C ₄ haloalkoxy groups, such as 1- or 2-bromoethoxy, 3-bromo -n- propoxy, 2, 2,2
-Trifluoroethoxy, 1- or 2-fluoroethoxy or a trifluoromethoxy group;
Examples of the _1- C ₄ alkylthio C ₁ -C ₄ alkyl group include:
Examples include a methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, methylthioethyl or ethylthioethyl group, and a C ₁ -C ₄ alkylsulfinyl C ₁
Examples of the —C ₄ alkyl group include methylsulfinylmethyl, ethylsulfinylmethyl, n-propylsulfinylmethyl, isopropylsulfinylmethyl, n
-Butylsulfinylmethyl, methylsulfinylethyl or ethylsulfinylethyl group;
The ₁ -C ₄ alkylsulfonyl C ₁ -C ₄ alkyl group, methylsulfonylmethyl, ethylsulfonyl methyl, n- propylsulfonyl methyl, isopropyl sulfonyl methyl, n- butylsulfonyl methyl, methyl sulfonyl ethyl or ethylsulfonyl ethyl group And the C ₁ -C ₄ haloalkylthio C ₁ -C ₄ alkyl group includes trifluoromethylthiomethyl or 2,2
And 2,2-trifluoromethyl ethylthiomethyl group and the _like, C 1 -C ₄ The haloalkylsulfinyl _C 1 -C ₄ alkyl group, trifluoromethyl sulfinyl methyl or 2,2,2-trifluoroethyl sulfinyl methyl And the like. Examples of the C ₁ -C ₄ haloalkylsulfonyl C ₁ -C ₄ alkyl group include a trifluoromethylsulfonylmethyl and a 2,2,2-trifluoroethylsulfonylmethyl group.

In the compound of the general formula (1), preferably, R ¹ is a phenyl group substituted by a fluorine or chlorine atom, R ² is a methylthiomethylphenyl group or an ethylthiomethylphenyl group, The ring comprising B is a pyridine, thiophene, furan, dihydropyran, indole, tetrahydropyridine, isoxazole or quinoline ring, R ³ is a hydrogen atom, a methyl group or an ethyl group, more preferably R ¹ is A chlorine atom-substituted phenyl group, R ² is a methylthiomethylphenyl group, a ring comprising A and B is a pyridine, thiophene, furan, dihydropyran or indole ring, and R ³ is a hydrogen atom or It is a methyl group.

In the compound of the general formula (1), R ¹ is preferably a chlorophenyl group and R ² is a methylthiomethylphenyl group.

The compound represented by the general formula (1) has a C = N
There are two types of geometric isomers, an entgegen (E) form and a tuzamen (Z) form derived from the bond, and the compound of the present invention may use the E form or Z form alone or as a mixture thereof. .

The compound (1) of the present invention is, for example, a hydrochloride,
It can be an inorganic or organic acid salt such as sulfate, nitrate, phosphate and the like. As long as they can be used as agricultural and horticultural insecticides, they are included in the present invention.

The compound represented by the general formula (1) of the present invention can be produced by the following reaction formula (1), but is not limited thereto.

[0012]

Embedded image [Wherein, A, B, R ¹ , R ² , R ³ , and R ⁴ have the same meanings as described above. That is, the compound of the present invention represented by the general formula (1) is different from the aldehyde compound represented by the general formula (2) and the general formula (3)
By condensing with a hydrazone compound represented by the formula:

The reaction between the aldehyde compound represented by the general formula (2) and the hydrazone compound represented by the general formula (3) is carried out without a solvent or in an appropriate solvent. Solvents that can be used include alcohols such as methanol and ethanol, toluene, aromatic hydrocarbons such as xylene,
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, 1,4
Ethers such as dioxane; halogenated hydrocarbons such as dichloromethane and chloroform; aliphatic hydrocarbons such as pentane, hexane and heptane; alicyclic hydrocarbons such as cyclohexane; and pyridines such as pyridine. In some cases, these mixtures or a mixture with water can be used as a solvent.

The use ratio of the aldehyde compound represented by the general formula (2) to the hydrazone compound represented by the general formula (3) is usually 0.5 to 2 moles, preferably 0 to 2 times, of the former. The molar ratio is preferably about 0.8 to 1.2 times mol. The reaction proceeds favorably in a temperature range from usually −10 ° C. to the boiling point of the solvent used in the reaction, and is generally completed in about 1 to 10 hours.

In the above reaction, many of the aldehyde compounds represented by the general formula (2) used as starting materials are known (for example, 2-pyridinecarboxaldehyde,
3-pyridinecarboxaldehyde, 4-pyridinecarboxaldehyde, 4-methyl-3-thiophencarboxaldehyde, 5-methylfurfural, indole-3-carboxaldehyde, and the like) can be industrially easily obtained.

The hydrazone compounds represented by the general formula (3) are disclosed in JP-A-9-3038 and JP-A-9-278.
No. 744, JP-A-10-7637 and the like can be easily synthesized.

The compound of the present invention obtained by the above-mentioned method can be easily isolated and purified from the reaction mixture by a usual separation means, for example, a solvent extraction method, a recrystallization method and a column chromatography method.

When the compound of the formula (1) of the present invention is used, it is generally used in the field of agrochemical production, either as it is or according to the purpose of use, by mixing an agrochemical adjuvant to promote or stabilize the effect. Powder,
Fine granules, granules, wettable powders, flowables, wettable powders (dry flowables), aqueous solvents, liquids, EWs, emulsions, microcapsules, oils, aerosols, heated fumigants (mosquito coils, Fogging and other fogging agents,
It can be used as a composition in any pharmaceutical form such as a non-heat fumigant or a bait.

In use, these various preparations can be used directly as they are, or can be used after being diluted to a desired concentration with water.

[0020] The agricultural chemical adjuvants include carriers (diluents) and other adjuvants such as spreading agents, emulsifiers,
Wetting agents, dispersants, fixing agents, disintegrants and the like can be mentioned.

Examples of the carrier include a liquid carrier and a solid carrier. Examples of the liquid carrier include aromatic hydrocarbons such as toluene and xylene; alcohols such as butanol, octanol and glycol; amides such as dimethylformamide; Examples thereof include sulfoxides such as sulfoxide, methylnaphthalene, animal and vegetable oils, fatty acids, fatty acid esters, and petroleum fractions such as kerosene and light oil, and water.

Examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust and the like.

Surfactants are usually used as emulsifiers or dispersants, for example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. Surfactants, nonionic surfactants, and zwitterionic surfactants are exemplified.

Examples of the spreading agent include polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl ether. Examples of the wetting agent include polyoxyethylene nonyl phenyl ether dialkyl sulfosuccinate. Examples thereof include carboxymethylcellulose and polyvinyl alcohol, and examples of the disintegrant include sodium ligninsulfonate and sodium lauryl sulfate.

Further, by combining and using two or more of the compounds of the present invention, it is possible to exhibit more excellent insecticidal activity, and it is also possible to develop other physiologically active substances such as arelesrin, phthalthrin, permethrin, deltamethrin, fenvalerate, Pyrethroid insecticides such as cycloprothrin and various isomers, pyrethrum extract, DDVP
(Dichlorvos), fenitrothion, diazinon,
Organophosphorus pesticides such as Temefos, carbamate pesticides such as NAC (carbaryl), PHC (propoxur), BPMC (fenbucarb), pirimicarb and carbosulfan; chloronicotinyl pesticides such as imidacloprid and acetamiprid; Insecticide, IG
R, acaricide or fungicide, nematocide, herbicide, plant growth regulator, fertilizer, BT agent, insect hormone, other pesticides, etc. to make more effective multipurpose composition And a surplus effect can be expected.

Further, for example, piperonyl butoxide, sulfoxide, safloxane, NIA-1682
4 (O-sec-butyl-O-propargylphenylphosphonate), DEF (S, S, S-tributylphosphotrithioate) and the like, which are known as synergists for pyrethrin, are added to the composition of the present invention. It can also increase the effectiveness of things.

If necessary, an antioxidant or an ultraviolet absorber such as BHT or BHA may be added to the composition of the present invention.
By adding phenols, arylamines such as α-naphthylamine, or benzophenone-based compounds as stabilizers as appropriate, a composition having more stable effects can be obtained.

The content of the active ingredient in the composition of the present invention depends on the form of preparation, application method and other conditions. In some cases, only the active ingredient compound may be used.
To 95% (by weight), preferably 0.05 to 80% (by weight).

The amount of the composition of the present invention varies depending on the dosage form, method of application, timing, and other conditions. However, when the composition is used as an insecticide for agricultural and horticultural use, a pesticide for forest pests, and a pesticide for pasture pests, , Usually 0.5% of the active ingredient per 10 ares.
To 300 g, preferably 2 to 200 g, and as an insecticide for sanitary insect pests, the amount of the active ingredient is usually 1 per m ^2.
２００200 mg, preferably 1-100 mg, are used. For example, per 10 ares, the powder is 1 to
120 g, granules are 5-300 g of active ingredient, emulsion,
Wettable powder, flowable, granule wettable powder, EW (emuls
ion in water) agent is 0.5 to 1
Use in the range of 00g. However, in special cases, it is possible, and sometimes even necessary, to exceed or fall below these ranges.

When the compound of the general formula (1) of the present invention is used for controlling parasites, the compound is used at a dose equivalent to, for example, 0.1 to 200 mg / kg per human or animal body weight. be able to. Precise dosages for a given condition can be determined routinely and will depend on a variety of factors, such as the compound of the present invention used, the type of parasite used, the formulation used, the dosage form employed and the infection of the parasite. Depends on the condition of the human or animal.

Specific pest names to which the insecticidal composition of the present invention can be applied are listed below.

As the Hemiptera, for example, leafhopper (Nephotettix c)
indictes), Scotch planthopper (Sogatel)
lafurcifera), brown planthopper (Nila)
parvata lugens), Japanese brown planthopper (L
aodelphax striatelus, Riptortus clavatu
s), southern stink bug (Nezara virid)
ula), Nashigumbai (Stephanitis n)
ashi), Whitefly on whitefly (Trialeuro)
des vaporariorum, cotton aphid (Aphis gossypiii), peach peach aphid (Myzus persicae), mosquitoes (Unasqis yanonensis), Lepidoptera [Lepidoptera], for example, Pyrgynophora
oniella), Konaga (Plutella xyl)
ostella), cotton moth (Promalactis)
inonisema), Kokakumon Hamaki (Adox)
ophores orana) and Mameshin Iga (Leg)
uminivora glycinivorell
a), Combophyllum (Cnaphalocrocis)
medinalis), Nikameiga (Chilo su)
peresalis, Awanomeiga (Ostri)
nia furnacalis), armyworm (Mame)
str. brassicae), armyworm (Pse
udoletia separata, Spodoptera litura, Spodoptera beetle (Parnaraguttata), and white butterfly (Pieris rapae-crucivor)
a), Heliothis spp.,
Noctuid (Agrotis spp.), Tobacco (Hel)
icoverpa spp. ), Coleoptera [Coleop
tera], for example, Douganebuui (Ano)
mala cuprea) and mamekogane (Popill)
ia japonica, rice weevil (Echin)
ocnemus squameus, rice weevil (Lissorhoptrus oryzophil)
us), rice dung beetle (Olema oryza)
e), the beetle beetle (Anthrenus)
verbasic), Kokunusto (Tenebroid)
es mauritanicus, weevil (S)
Itophilus zeamis, and the Japanese ladybird (Henosepilachna vigin)
tiocuncuncata), Azuki weevil (C
allobruchus chinensis, pine beetle (Monochamus alte)
rnatas) and the beetle beetle (Aulacophora)
femoralis), Leptinotarsa decemlineata (Leptiontarsa decemline)
ta), Fedon Cochleariae (Phaedon)
cochleaias, diablotica (Diabr)
otica spp. ), Hymenoptera [Hymenopte
ra], for example,
rosae japonensis), Rurichu range wasp (Arge similis), Diptera [D
iptera], for example,
lex pipiens fatigans, Aedes aegypti, soybean flies (Ashondyls sp.), fly (Hylemya plateura), housefly (M)
usca domestica viclna), sea turtle fly (Dacus cucurcitae), rice leaf fly (Agromyza oryzae), maggot fly (Lucliaspp.), Aphididae [Aphan
iptera], for example, a human flea (Pulex
irritans), Coleopteran flea (Xenop)
sylla cheopis, dog flea (Cteno)
cephalides canis), Coleoptera [Thy
sanoptera], for example, Thrips thrips dorsum
s), thrips thrips (Thrips tabac)
i), Thrips palmi (Thrips pal)
mi), Rice thrips (Baliothrips b)
ifomis), lice (Anoplura), such as white lice (Pediculs hum)
anus corporis, psyllium (Pthiru)
s pubis), the order Psocoptera [Psocopte]
ra], for example,
pulsatorium), scallop (Lipo)
ceres botrychophilus, Orthoptera, for example, Kerala (Grylotalpa africana), Tonosama grasshopper (Locusta migratori)
a), Kobaneiago (Oxya yezoensi)
s), German cockroach (Blattella ger)
manlica), black cockroach (Periplane)
ta fluginosa, termite pests, for example, Reticuliter
mes sparatus, house termite (Copt)
otermes formosanus, spider mites, for example, spider mite (Tetranychus)
urticae), Tetranyc
hus Kanzawa, mandarin orange mites (Pano)
nychus citri, apple spider mite (Pano)
nychus ulmi), Yellow Mite (Eote)
tranychus carpini), citrus red mite (Phyllocoptrutta oleivor)
a) As a plant parasitic nematode, for example, sweet potato nematode (Meloidogyne incog)
nita), Negusare nematode (Pratylenc)
hus sp. ), Soy cyst nematode (Hete
rodera glycines), other pests,
As an unpleasant animal, a sanitary pest, or a parasite, for example, a black mussel (Pomacea canaliculat)
a), gastropods such as slugs (Incilaria sp.), African scabies (Achatina fulica), and gastropods (A)
rmadillidium sp. ), Isopoda such as Coleoptera, Centipede, and Liposc
elis sp. Beetles such as Ctenol
episma sp. Spots such as Pulex s
p. , Ctenocephalides sp. Fleas such as Trichodictes sp. Lice such as Cimex sp. Bed bugs such as bed bugs, ox tick (Boophilus microplu)
s), Haemaphysalis
animal parasitic mites such as C. longicornis),
Dermatophagoides.

Examples of the compound of the formula (1) of the present invention include the compounds shown in Table 1 below.

[0034]

[Table 1] In the above table, R ¹ represents a 4-chlorophenyl group, and R ² represents 4
-Represents a (methylthiomethyl) phenyl group.

[0035]

The present invention will be described below with reference to examples.
The present invention is not limited only to these.

Manufacturing example(4-((((pyrid-2-ylmethylene) azamethyle
Azamethylene) (4-chlorophenyl) methyl)
Preparation of phenyl) methylthiomethane (Compound No. 1)  4-chloro-4 '-(methylthiomethyl) benzopheno
50 mg of 300 mg (1.0 mmol) of hydrazone
With ethanol. In addition, 2-pyridyl
Add aldehyde (110 mg, 1.0 mmol) and add room temperature
For 8 hours. Concentrate under reduced pressure and remove the residue with water and ethyl acetate.
And the ethyl acetate layer was washed with a saturated saline solution.
After dehydration with sodium sulfate, the mixture was concentrated under reduced pressure. Residue
Purification by Ricagel chromatography
210 mg of the compound was obtained.

The NMR spectrum of the mixture of geometric isomers of the compound produced in the same manner as in the above Production Example is as follows.

¹ H-NMR (CDCl ₃ ) δ ppm; Compound No. 1: 8.65 (d, 1H), 8.57 (d, 1)
H), 7.82 (d, 1H), 7.65 to 7.70.
(M, 3H), 7.29-7.42 (m, 7H), 3.
71 (d, 2H), 2.02 (d, 3H).

¹ H-NMR (CDCl ₃ ) δ ppm; Compound No. 2: 8.83 (d, 1H), 8.57 to 8.6
4 (m, 2H), 7.95 to 7.98 (m, 1H),
7.66 (d, 2H), 7.29 to 7.43 (m, 7
H), 3.72 (d, 2H), 2.03 (d, 3H).

¹ H-NMR (CDCl ₃ ) δ ppm; compound number 3: 8.63 to 8.66 (m, 2H), 7.6
6 (d, 2H), 7.20 to 7.50 (m, 9H),
3.72 (d, 2H), 2.03 (d, 3H).

¹ H-NMR (CDCl ₃ ) δ ppm; Compound No. 4: 8.82 (d, 1H), 7.61 to 7.6
5 (m, 2H), 7.29 to 7.41 (m, 8H),
3.72 (d, 2H), 2.39 (s, 3H), 2.0
2 (d, 3H).

¹ H-NMR (CDCl ₃ ) δ ppm; Compound No. 5: 8.35 (d, 2H), 7.61 (d, 2)
H), 7.28-7.41 (m, 6H), 6.72.
(D, 1H), 6.11 (d, 1H), 3.71 (d,
2H), 2.35 (d, 3H), 2.05 (d, 3
H).

¹ H-NMR (CDCl ₃ ) δ ppm; Compound No. 6: 8.04 (d, 1H), 7.58 to 7.6
1 (m, 2H), 7.20 to 7.39 (m, 6H),
6.38 (m, 1H), 4.24 (s, 2H), 3.7
9 (t, 2H), 3.70 (d, 2H), 2.34 ~
2.37 (m, 2H), 2.02 (d, 3H).

¹ H-NMR (CDCl ₃ ) δ ppm; Compound No. 7: 8.86 (s, 1H), 8.72 (br,
1H), 7.79 (d, 2H), 7.03 to 7.45.
(m, 10H), 3.73 (d, 2H), 2.02
(D, 3H).

Next, the insecticidal composition will be specifically described with reference to formulation examples.

Formulation Example 1 Emulsion 65 parts of a mixture of xylene-dimethylsulfoxide was added to and dissolved in 20 parts of the compound of Compound No. 1, and then 15 parts of a mixture (8: 2) of an alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate were mixed. And

Formulation Example 2 Wettable powder 35 parts of kaolin, 30 parts of clay and 7.5 parts of diatomaceous earth are mixed with 20 parts of compound No. 1 and 7.5 parts of a mixture of sodium lauryl sulfate and sodium dinaphthylmethanesulfonate (1: 1). Was mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Dust A powder was prepared by adding 2 parts of silicic anhydride and 97 parts of a mixture of talc and calcium carbonate (1: 1) to 1 part of the compound of Compound No. 1 and mixing and pulverizing the mixture to obtain a sufficiently uniform mixture.

Formulation Example 4 Granules Compound 2 of compound No. 1 was mixed with bentonite fine powder 48
, 48 parts of talc, and 2 parts of sodium ligninsulfonate, and then water was added and kneaded until uniform. Next, the mixture was granulated through a granulator and passed through a granulator, a dryer and a sieve to obtain granules having a particle size of 0.6 to 1 mm.

Formulation Example 5 Oil Agent 0.5 parts of piperonyl butoxide was added to 0.1 part of the compound of Compound No. 1 and dissolved in white kerosene to make the whole 100 parts to obtain an oil agent.

Formulation Example 6 Flowable agent Compound 5 of Compound No. 7 was added to Newkalgen F
5 parts of S-3 (a dispersant manufactured by Takemoto Yushi Co., Ltd.), Antifo
rm 422 (a defoamer manufactured by Rhone-Poulenc) and 76.3 parts of distilled water were mixed, and the mixture was mixed at 45 rpm at 1,000 rpm using a sand grinder mill (manufactured by Igarashi Oki).
After milling for 8 minutes, 8 parts of propylene glycol, 5 parts of an aqueous solution of 2% xanthan gum and Proxcel GXL
(Zeneca antifungal agent) 0.5 part was added and mixed to obtain a flowable agent.

Next, the biological effect of the compound represented by the general formula (1) according to the present invention will be specifically described with reference to test examples.

Test Example Cotton Aphid Insecticidal Test An emulsion prepared according to the above formulation example was diluted with water so that the active ingredient was 20% to obtain an aqueous solution containing the active ingredient at a concentration of 800 ppm. New Grameen 2
It was added so as to be diluted 1000 times. A leaf leaf of a 4.5 cm square cucumber is placed on a cotton wool moistened sufficiently with water, the back of the leaf facing up, and the cotton aphid wingless adult 2-
Three were released. After about 16 to 18 hours, the adults were removed and the number of larvae (1st instar) was adjusted to 10 heads / disk.
280 mmHg of the diluted aqueous solution (2 ml) in a spray tower
At a spray pressure of Seal container after air drying (diameter 8cm x 4
cm) and kept in a constant temperature room at 25 ° C and 16L8D. Five days after the treatment, the number of dead insects was investigated, and the mortality was calculated.

Compound No. 1 showed a mortality of 80% or more.

[0055]

Industrial Applicability The novel azine derivative of the present invention has excellent insecticidal activity and is effective in pest control in paddy fields, fields, orchards, forests or environmental sanitation.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) A01N 43/38 A01N 43/38 4C056 43/40 101 43/40 101C 4C204 101K 4H011 43/42 101 43/42 101 43 / 80 101 43/80 101 C07D 209/14 C07D 209/14 211/70 211/70 213/20 213/20 215/12 215/12 261/08 261/08 307/52 307/52 333/22 333/22 (72) Inventor Reiji Ichinose 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture In-house (72) Inventor Shigeru Shige 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Co., Ltd.F-term (reference) 4C023 DA03 4C031 BA04 4C037 HA26 4C054 AA05 CC02 DD01 EE04 EE16 FF01 4C055 AA01 BA01 BA02 BA30 BB17 CA01 CA02 CA05 CA06 CA13 CA30 CA39 CB17 DA01 DA30 DB17 4C056 AA01 AB01 AC01 AD01 AE03 FA13 FB01 FC01 4C204 BB02 CB03 DB13 EB02 BC01 BC01 BC01 BC01 4 DA02 DA15 DA16

Claims (2)

[Claims] 1. A compound of the general formula (1) (Wherein, R ¹ is a halogen atom, a C ₁ -C ₄ alkyl group,
A phenyl group which may be substituted with a halo C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group or a halo C ₁ -C ₄ alkoxy group, wherein R ² is a C ₁ -C ₄ alkylthio C ₁
-C ₄ alkyl group, C ₁ -C ₄ alkylsulfinyl C
₁ -C ₄ alkyl _group, C 1 -C ₄ alkylsulfonyl C
₁ -C ₄ alkyl _group, C 1 -C ₄ haloalkylthio _{C 1}
A phenyl group having, as a substituent, a —C ₄ alkyl group, a C ₁ -C ₄ haloalkylsulfinyl C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkylsulfonyl C ₁ -C ₄ alkyl group, and A is —CHR ³ -O -, - ^CR 3 = N
^{-, - CR 3 = CR 3} -, - CHR 3 -, - S -, - O
— Or —NR ⁴ —, and B is —CHR ³ —O—, —C
^{HR 3 -CHR 3 -, - CR} 3 = CR 3 -, - CR 3 =
N— or —NR ⁴ —, and R ³ are each independently a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, a halo C ₁ —.
C ₄ alkyl group, C ₁ -C ₄ alkoxy group, halo C _1-
Two C ₄ alkoxy groups or two adjacent R
³ may together form a 5- to 7-membered ring, and R ⁴ is a hydrogen atom or a C ₁ -C ₄ alkyl group) or an agriculturally acceptable salt thereof. 2. An insecticidal composition comprising the azine derivative according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.