JPH0341004A - Insecticidal and miticidal agent - Google Patents

Abstract

PURPOSE:To obtain insecticidal and miticidal agent exhibiting activity against insect such as Aphididae, Delphacidae, plutella xylostella, Curculionoidae and Musca domestica and Acarina containing 2,3-disubstituted-4-hydroxyquinoline derivative as active ingredient. CONSTITUTION:One or more compounds expressed by formula I [R<1> is H or R<3>CO (R<3> is lower alkyl); R<2> is H, methyl or ethyl; A is CH2CH=CH, expressed by formula II, by formula III or CH=CHCH2] are contained in the objecsve agent as active ingredient. In the using, the agent is mixed with carrier, surfac tant or dispersant, etc., and formed to suitable formulation such as emulsion or powder. Contained amount of active ingredient in the subject agent is 1-50wt.% for emulsion and 0.3-25wt.% for powder. Besides, the compound expressed by formula I is a novel compound and 2-(trans-1-nonenyl)-3-methyl-4- acetoxyquinoline, etc., is a concrete example.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention provides an extremely excellent insecticide containing a novel 2,3-disubstituted-4-hydroquine quinoline derivative as an active ingredient.
This invention relates to insecticides and acaricides that have acaricidal effects.

[Conventional technology]

BACKGROUND ART Conventionally, various natural ingredients and synthetic substances having insecticidal and acaricidal activities have been researched, developed, and put into practical use.

In addition, as a quinoline substance, 3p-bromophenyl-
It is known that 1-〇-hydroxystyrylbenzo[f]quinoline has acaricidal and fungicidal activity [Ve
stsi^kad, NavukBSSR,Ser,
Khim, Navuk, (3), 76-8 (1
987)).

In addition, bactericides and insecticides containing copper complexes of 8-alfuki/quinolines as active ingredients are also known (Japanese Patent Publication No. 347/1986).
(No. 38) However, the insecticidal activity of these compounds is not sufficient in terms of strength, selectivity, etc.

[Problem to be solved by the invention]

Various conventionally known substances with insecticidal and acaricidal activity cannot be said to have sufficient efficacy due to the problem of insecticide resistance in recent years, and there is a demand for the development of new insecticides and acaricides with excellent activity. .

The object of the present invention is to provide an excellent insecticide and acaricide that meets this demand.

[Means to solve the problem]

The present inventors previously synthesized microbial metabolites and their analogs in a pure chemical manner to form a strong leukotriene D.

A novel 2,3-disubstituted-4 substance that has antagonistic effects and effectively acts on the immune system and cardiac blood flow, which are particularly important for maintaining the body of mammals including humans, and is effective in the treatment of immune diseases and brain diseases.
-Invented a hydroxyquinoline derivative and its production method,
It was filed as Japanese Patent Application No. 1983-319231.

The present inventors further studied the effects of this substance and found that
They discovered that it has excellent insecticidal and acaricidal activity, and completed the present invention.

The present invention relates to the general formula (1) [wherein 81 represents a hydrogen atom or R'CD- (R3 represents a lower alkyl group], R2 represents a hydrogen atom, a methyl group, or an ethyl group, and A is represented by This is an insecticide and acaricide containing one or more 2,3-disubstituted-4-hydroxyquinoline derivatives as an active ingredient.

When R1 in the formula represents a hydrogen atom, the compound represented by the above formula (I) which is an active ingredient of the present invention is a 2,3-disubstituted-4-quinolone derivative represented by the formula (II). Although there is a tautomeric relationship with , this compound is also included in the present invention.

[In the formula, R' and A have the same meanings as above] The 2,3-disubstituted-4-hydroquinequinoline derivatives which are the active ingredients of the present invention are all new compounds that have not been described in any literature. Representative compounds are listed below.

2-(trans-■-nonenyl>-3-methyl-4-acetoxyquinoline 2-(cis-1-nonenyl)-3-methyl 4-acetoxyquinoline 2-(trans-1-)unyl)-3-methyl -4-quinolone 2-(dis-l-nonenyl)-3-methyl-4-quinolone 2-(trans-2'-nonenyl)-3-methyl-4-
Acetoxyquinoline 2-(trans-2-nonenyl)-3-methyl-4-quinolone 2-(l-hydroxy-2-nonenyl>-3=methyl-
4-acetoxyquinoline 2-(1-hydroxy-2-nonynyl)-3-methyl-
4-quinolone 2-(trans-1-hydroxy-2-nonenyl)-3
-Methyl-4-acetoxyquinoline 2-(trans-1-hydroxy-2-nonenyl)-3
-methyl-4-quinolone and the like.

Note that the numbers attached to the names of the compounds are cited in the following examples.

2,3-disubstituted -4- represented by the above general formula N) of the present invention
Insecticides containing hydroxyquinoline derivatives as active ingredients are
Hemiptera such as 7 aphids, planthoppers, and 5 stink bugs, Lepidoptera such as Spodoptera nigra, Kona, Lepidoptera such as snail moths, Coleoptera such as occidentals and potato beetles, Diptera such as houseflies and Culex mosquitoes, and cockroaches. It has particularly remarkable activity against insects of the order Ophthalmos, other orders of the Order Pteroptera, and orders of the order Thripsidae, as well as pests such as spider mites, ticks, and mites, and mites.

The insecticide and acaricide of the present invention may use one or more of the compounds represented by the general formula (1) as an active ingredient as they are, but are usually used in the formulation of first-class agricultural chemicals. It can be mixed with solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants, other formulation auxiliaries, baits, etc. in a conventional manner to form emulsions, liquids, wettable powders, powders, granules, oils, and aerosols. It is used in appropriate dosage forms such as , floatables, poison baits, etc.

In addition, examples of solid carriers include talc, bentonate,
Clay, kaolin, diatomaceous earth 1 vermiculite,
Examples of liquid carriers include white carbon, calcium carbonate, etc., and examples of liquid carriers include methanol, n-hexanol,
ethylene glycol.

Alcohols such as cellosolve, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, aliphatic hydrocarbons such as kerosene and kerosene, and benzene.

Aromatic hydrocarbons such as toluene, xylene, and methylnaphthalene; halogenated hydrocarbons such as dichloroethane, trichloroethylene, and carbon tetrachloride; ethers such as diethyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; acetonitrile; Examples include nitriles such as butyronitrile, acid amides such as dimethylformamide and dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, and water.

Examples of gas carriers include LPG and fluorocarbon gas.

Examples include air, nitrogen, carbon dioxide, dimethyl ether, and the like.

Examples of surfactants and dispersants for emulsification, dispersion, and spreading include alkyl sulfates, alkyl (aryl) sulfonates, and polyoxyalkylene alkyl (
(aryl) ethers, polyhydric alcohol esters, lignin sulfonates, etc. are used.

Further, as adjuvants for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate, etc. are used.

The above-mentioned carrier, surfactant, dispersant and auxiliary agent may be used alone or in combination, if necessary.

The content of the active ingredient of the insecticide and acaricide in the present invention is:
For emulsions it is usually 1 to 50% by weight, for powders it is usually 0.3%.
Appropriate amounts are ~25% by weight, usually 1~90% by weight for wettable powders, and 0.5~10% by weight for granules.

These preparations can be used as they are or after being diluted. It can also be used in combination with other insecticides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, soil conditioners, synergists, etc.

〔Example〕

Next, the present invention will be described in more detail by citing examples and effects thereof, but the present invention is not limited only to these examples.

Production Example 1 Production Example of Compounds 1 and 2 Octyltriphenylphosphonium Bromide 218
mg (0.48 mmol) of tetrahydro7ran 3 ml
In the solution, n-butyllithium Q, 43 mmol of hexane solution 0.29 ml! and stir for 5 minutes at room temperature.

After cooling this solution to -78°C, 1.43 g (8 mmol) of hexamethylphosnextriamide was added and stirred for 5 minutes, and then 2-formyl-3-methyl-4-
Acetoxyquinoline 91.6 mg (0.40 mmo
l) by adding 2-solution of -7 in tetrahydrofuran.
Stir at 8°C for 15 minutes and at -42°C for 30 minutes. The reaction solution was added to 20 mg of water, extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 2-(trans-1 13 ■ of nonenyl)-3-methyl-4-acetoxyquinoline (yield: $10%) and 15 ■ of 2-(cis-1-nonenyl)-3-methyl-4-acetoxyquinoline (yield: 12%) are obtained.

2-(trans-1-nonenyl)-3-methyl 4-acetoxyquinoline [Compound 1] Melting point 74-75°C NMR (CDCIs) δ = 0.90 (t, J = 7Hz, 3H) 1.2
~1.5 (m, 1ON), 2.31 (s, 3N)
.

2.33-2.40 (m, 2H), 2.51 (s,
3H).

6.80 (d, J = 15.4Hz, 1N).

7.08 (dt, J = 15.4Hz, J = 7.
1Hz, IH).

7.4-7.8 (+n, 3B), 8.04 (d,
J = 8.8 Hz, IH) 2-(cis-1-nonenyl)-3-methyl-4-acetoxyquinoline [Compound 2
] NMR (CDC13) δ-0,84 (t, J=6Hz 3H) 11-1.6
(m, 10)1).

2.2-2.7 <m2)1), 2.26(s,
3H).

2.49 (s, 3H), 6.02 (dt, J=1
2Hz, J = 711z, IH).

6.61 (d, J=12Hz, IH) 7, 3-8
．． 1(m, 4t()) Example 1 10% by weight of polyoxyethylene alkyl allyl ether was added to 20% by weight of Emulsion Compound 1, 20% by weight of N,N-dimethylformamide, and 50% by weight of xylene, and mixed uniformly.
It was dissolved to obtain an emulsion.

Example 2 Wettable powder compound 225% by weight, clay 30% by weight, diatomaceous earth 3
5% by weight of calcium lignin sulfonate, 3% by weight of calcium lignin sulfonate, and 7% by weight of polyoxyethylene alkyl allyl ether were uniformly mixed and pulverized to obtain a wettable powder.

Example 3 A powder was obtained by uniformly mixing 12% by weight of a powder compound, 60% by weight of clay, 37% by weight of talc, and 1% by weight of calcium stearate.

Example 4 Granule compound 25% by weight, bentonite 40% by weight, talc 5
3% by weight and 2% by weight of calcium ligninsulfonate were uniformly pulverized and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation and drying to obtain granules.

Next, tests and results showing the effects of the insecticide and acaricide of the present invention will be shown.

Test Example 1 Efficacy against green peach aphid (wingless viviparous female adult) A test sample prepared according to Example 1 was mixed with a surfactant (0
A piece of cabbage leaf (5 cm x 5 cm) inoculated with 10 wingless viviparous female adult green peach aphids was immersed in a test solution diluted to too ppm with water containing 0.01%) for 10 seconds. After air drying, a plastic cassop with a diameter of 9 am was immersed. The insects were placed in a thermostatic chamber at 25°C, and the number of live and dead insects was counted after one day to determine the mortality rate.

The results were as shown in Table 1.

Table l Mortality rate (%) - (Number of dead/J!l insects) Ten female adult spider mites were inoculated onto the leaves. One day after inoculation, a test sample prepared according to Example 1 was added to the sample with water containing a surfactant (0.01%).
The test solution diluted to ppm is 10ml in a spray tower! It was defeated. After the treatment, the insects were left in a constant temperature room at 25°C, and the number of live and dead insects was examined after 2 days to determine the mortality rate.

The results were as shown in Table 2.

Table 2 Mortality rate (%) = (Number of dead insects/Number of insects released)

Claims (1)

[Claims] 1. Formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 represents a hydrogen atom or R^3CO- (R^3 represents a lower alkyl group), and R^ 2 indicates a hydrogen atom, methyl group or ethyl group, A is -CH_2CH=CH-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or -CH=CHC
An insecticide or acaricide containing one or more 2,3-disubstituted-4-hydroxyquinoline derivatives represented by the formula H_2- as an active ingredient.