JPH07112901A - Insecticidal method - Google Patents

Abstract

PURPOSE:To provide an insecticidal method in which perfect insecticidal effects can be obtained in comparison with a conventional application method and the residue in soil and crops can simultaneously be reduced to improve the operating efficiency. CONSTITUTION:This insecticidal method is carried out by applying a liquid formulation of a systemic insecticidal compound in a site of a planting hole and/or an adjacent peripheral part thereof or plant feet of flowering and ornamental plants and/or adjacent peripheral parts thereof in and/or after planting a seedling of fruit vegetables in an amount so as to provide 0.005-0.025g, preferably 0.01-0.02g effective concentration of the compound based on one plant body. A compound expressed by formula I [R is H, an acyl, an alkyl or a substitutive heteroarylalkyl; A is H, an alkyl or a bivalent group binding to B; B is an alkyl, SR, a group expressed by formula II or a bivalent group binding to A; Y is N or CT<1> (T<1> is H or a substitutive alkyl); X is an electron attractive group], e.g. 1-(6-chloro-3-pyridylmethyl)-N-nitro-imidazolidin-2- ylidenamine is cited as the systemic insecticidal compound.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a new insecticidal method.

[0002]

2. Description of the Related Art Nitroimino compounds described in JP-A-61-106854 are extremely low doses of insecticidal compounds, which are more effective than conventional organophosphorus and carbamate insecticides. is there. Further, conventionally, as the insecticidal method, spraying on the plant itself, spraying on pests and their habitat, and soil application (granule) have been widely performed. When pesticides are used, they are used in various formulation forms, and most of them are generally sprayed with emulsions, wettable powders, powders and granules. The conventional spraying has a lot of soil residue, crop residue, worker's chemical exposure during spraying, difficulty in working conditions, diffusion to the environment, excessive use for maintaining spraying effect, work efficiency, etc. You have a problem to solve. Also, depending on the pesticide component, the amount used is limited due to the residue of crops.

[0003]

Means for Solving the Problems The present inventors have now found a new insecticidal method which is excellent not only in the pest control effect but also in the dose concentration, environment and work. That is, in controlling the harmful insects of fruits and vegetables, at the time of planting the seedlings of the fruits and / or after planting, at the planting site and / or the adjacent peripheral portion, and also the plant origin of the flowers and / or An insecticidal method, which comprises applying a liquid formulation of a systemic insecticidal compound to the peripheral area. Surprisingly, by using such an insecticidal method, it is possible to obtain a perfect insecticidal effect by precise application of the active ingredient to the target plant body, as compared with the conventional spraying effect, and at the same time, in the soil. Residues and crop residues can be reduced, and work efficiency can be improved.

The penetrating insecticidal compound used in the insecticidal method of the present invention is represented by, for example, the following formula (I).

[Chemical 13] In the formula, R represents a hydrogen atom, acyl, alkyl or optionally substituted heteroarylalkyl, A represents a hydrogen atom, alkyl or a divalent group bonded to B,
B is alkyl, -SR,

[Chemical 14] Or a divalent group or atom bonded to A, wherein R is the same as above, Y is ═N— or

[Chemical 15] Where T ¹ represents a hydrogen atom or an optionally substituted alkyl, and X represents an electron withdrawing group.

The compounds represented by the above formula (I) have already been disclosed in JP-A-60-218386 and 61-178981.
No. 61-267575 and No. 62-81382.
No. 2, JP-A-2-288859 and JP-A-2-28888.
No. 60 and No. 2-235881, and WO91 / 0.
It is a known one described in 4965 and the like.

In the compound of formula (I) provided for the insecticidal method, preferred examples of R are hydrogen atom, formyl, C _1-4 alkylcarbonyl, benzoyl, C _1-4 alkylsulfonyl, C _{1 -6} alkyl or heteroarylmethyl having at least one N atom and optionally up to 6 members optionally having a heteroatom, wherein A is a hydrogen atom, C _{1 -6} alkyl, ethylene, trimethylene, or

[Chemical 16] Wherein T ² is a hydrogen atom, C _1-4 alkyl or C
_1-4 alkylcarbonyl, B is C _1-6 alkyl,
-SR,

[Chemical 17] -S-, methylene or

[Chemical 18] Where R and T ² are as defined above and Y is = N
-Or = CH-, and X is nitro or cyano.

More preferably, R represents a hydrogen atom, formyl, acetyl, C _1-4 alkyl, 2-chloro-5-pyridylmethyl or 2-chloro-5-thiazolyl, and A
Is a hydrogen atom, C _1-4 alkyl, ethylene, trimethylene, or

[Chemical 19] Where T ² is methyl or ethyl and B is C
_1-4 alkyl, -SR,

[Chemical 20] -S-, methylene or

[Chemical 21] Where R and T ² are as defined above and Y is
Compounds where N- or = CH- are shown and X is nitro or cyano.

Particularly preferably, R represents 2-chloro-5-pyridylmethyl or 2-chloro-5-thiazolylmethyl, and A is a hydrogen atom, C _1-4 alkyl, ethylene, trimethylene, or

[Chemical formula 22] Where T ² is methyl or ethyl and B is C
_1-4 alkyl, -SR,

[Chemical formula 23] -S-, methylene or

[Chemical formula 24] Where R and T ² are as defined above and Y is = N
-Or = CH-, and X is nitro or cyano.

Specific examples of the compound of formula (I) provided for the insecticidal method of the present invention include the following compounds. 1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidin-2-ylideneamine, N-cyano-
N- (2-chloro-5-pyridylmethyl) -N'-methylacetamidine, 1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitro Ethylene, 1- (2-chloro-5-pyridylmethyl) -5-methyl-2-nitroimino-hexahydro-1,3,5-triazine, 1- (2-chloro-5
-Thiazolylmethyl) -3,5-dimethyl-2-nitroimino-hexahydro-1,3,5-triazine, 1-
(2-chloro-5-pyridylmethyl) -3,5-dimethyl-2-nitroimino-hexahydro-1,3,5-triazine, 1- (2-chloro-5-pyridylmethyl)-
2-nitromethylene-imidazolidine, 1- [N- (2
-Chloro-5-thiazolylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene, 3-
(2-chloro-5-pyridylmethyl) -2-nitromethylene-thiazolidine, 1- (2-chloro-5-pyridylmethyl) -2- (1-nitro-2-allylthioethylidene) imidazolidine,

1- (2-chloro-5-pyridylmethyl)
-2- (1-nitro-2-ethylthioethylidene) imidazolidine, 1- (2-chloro-5-pyridylmethyl)
2- (1-Nitro-2-β-methylallylthioethylidene) imidazolidine, methyl-[[3- (2-chloro-5-pyridylmethyl) -1-methyl-2-nitro] guanidinoformate, 1 -(2-chloro-5-pyridylmethylamino) -1-methylthio-2-nitroethylene, 1- (2-chloro-5-pyridylmethylamino)-
1-methylamino-2-nitroethylene, 1- (2-chloro-5-pyridylmethyl) -3-nitro-2-methylisothiourea, 3- (2-chloro-5-pyridylmethyl) -1 methyl-2 -Nitroguanidine, 1- (2-chloro-5-pyridylmethylamino) -1-dimethylamino-2-nitroethylene, 1- [N- (2-chloro-5
-Pyridylmethyl) -N-methylamino] -1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-pyridylmethyl) -N-methylamino] -1-dimethylamino-2- Nitroethylene,

3- (2-chloro-5-pyridylmethyl)
-1,1-dimethyl-2-nitroguanidine, 1- (2
-Chloro-5-pyridylmethylamino) -1-ethylamino-2-nitroethylene, 1-amino-1- [N-
(2-chloro-5-pyridylmethyl) -N-methylamino] -2-nitroethylene, 3- (2-chloro-5-pyridylmethyl) -1,3-dimethyl-2-nitroguanidine, 3- (2 -Chloro-5-pyridylmethyl) -1,
1,3-trimethyl-2-nitroguanidine, 1-amino-1- [N- (2-chloro-5-pyridylmethyl)-
N-ethylamino] -2-nitroethylene, 1- [N-
(2-chloro-5-pyridylmethyl) -Nn-propylamino] -1-methylamino-2-nitroethylene,
1- [N- (2-chloro-5-pyridylmethyl) -N-
Ethylamino] -1-ethylamino-2-nitroethylene, and 3- (2-chloro-5-pyridylmethyl) -3
-Ethyl-1-methyl-2-nitroguanidine and the like.

The above exemplified compounds are representative of the compounds of formula (I) and they are not limiting the insecticidal method of the present invention. In the present invention, specific examples of fruit vegetables and flowers of the target plant include, for example, eggplant, cucumber, tomato, melon, watermelon, sweet pepper, hops, etc., fruit vegetables,
Other examples include flowers such as chrysanthemums and roses. The insecticidal method of the present invention is particularly suitable for the homoptera (Homoptera) typified by aphids (Aphis gossypii, Pseudomonas aphid, etc.), and thrips typified by Thrips palmi (Thysanopter).
It can be applied extremely effectively and accurately to the control of a).
However, the insecticidal method of the present invention is not limited to these pests, but can be widely applied to the control of pests such as vegetables and horticultural crops such as flowers. The effective concentration of the insecticidal compound in the insecticidal method of the present invention is usually about 0.
005 g to about 0.025 g, preferably about 0.01 g
It is about 0.02 g. However, the effective concentration can be appropriately changed depending on the growth state of the target plant and the generation state of pests.

In carrying out the insecticidal method of the present invention,
For example, it can be applied using a soil disinfecting device usually used for soil disinfection, for example, a manual soil disinfecting device (HF-4X manufactured by Kyoritsu). Further, a soil treatment instrument conforming thereto can be used. Examples of the formulation of the insecticidal compound used in the insecticidal method of the present invention include liquid formulations such as emulsions, suspensions, emulsions, emulsion suspensions and emulsions. These formulations can usually be provided by known methods. Such a method is performed, for example, by mixing the active compound with a liquid diluent or a surfactant, and when water is used, an organic solvent is used as a cosolvent.

Examples of the liquid diluent include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, etc.). Methylene chloride etc.), aliphatic hydrocarbons [eg cyclohexane etc., paraffins (eg mineral oil fraction etc.)], alcohols (eg butanol, glycol and their ethers, esters etc.), ketones (eg acetone) , Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), a strong polar solvent (eg dimethylformamide, dimethyl sulfoxide etc.) and water.

The surfactants include nonionic and anionic surfactants [eg polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (eg alkylaryl polyglycol ethers, alkyl sulfonates, alkyl salts Sulfates, aryl sulfonates, etc.)], and albumin hydrolysis products. It is also possible to use colorants in the formulation, such as inorganic pigments (for example iron oxide, titanium oxide and Prussian blue) and alizarin dyes, azo dyes or metal phthalocyanine dyes. Mention may be made of organic dyes and also trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum, zinc. The preparation can contain, for example, 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of the active ingredient.

The predetermined formulation containing the osmotic insecticidal compound in the insecticidal method of the present invention contains, if necessary, other active compounds such as other insecticides, fungicides, acaricides, plant growth regulators and the like. Can also be present as a mixture. When other active compounds are contained, these active compounds are particularly preferably those having an osmotic migration property. As a typical example,
Examples thereof include triadimefon, bitertanol, phenarimol, tebuconazole, prochloraz, triflumizole, pyrifenox, triphorin, pefurazoate, hexaconazole, microbutanyl, propiconazole, diniconazole, fenpropimorph, bromconazole and the like. Next, the content of the present invention will be specifically described with reference to examples, but the present invention should not be limited to these.

[0017]

【Example】

Biological test: -Compound under test No. 1: 1- (6-chloro-3-pyridylmethyl)-
N-nitro-imidazolidine-2-ylideneamine No. 2: N-cyano-N- (2-chloro-5-pyridylmethyl) -N'-methylacetamidine No. 3: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene No. 4: 1- (2-chloro-5-thiazolylmethyl)
-3,5-Dimethyl-2-nitroimino-hexahydro-1,3,5-triazine

Test Example 1 Control test for aphids Drug preparation A 20% suspension of each test compound was prepared according to a conventional method,
The prescribed dose was provided. Crop Cucumber (variety: four leaves) 1 ward 5 strains 4 consecutive control Eggplant (variety: 1,000 Ryo No. 2) 1 ward 10 strains 2 consecutive control The test started from the growing period 42 days after transplantation. Treatment method 42 days after transplantation, using a manual soil disinfectant, approximately 1 from the root
Depth of about 1 cm diagonally from the place 5 cm away from the center of the root
A predetermined amount of drug (4 ml) was irrigated to 5 cm. The number of target pests was investigated on a predetermined investigation day (days after treatment). For cucumber, the central 3 strains of each plot and for eggplant, the central 6 strains of each plot were examined for the number of parasitic aphids, and the control value was calculated in comparison with the untreated plot. 35 days after the treatment with cucumber, the top 15 leaves of the strain were investigated. As a comparative control, 1% granules of each compound were dispersed at the root of test plants during the above treatment. The test results are shown in Tables 1 to 4.

[0019]

[Table 1]

[0020]

[Table 2]

[0021]

[Table 3]

[0022]

[Table 4]

[0023]

The insecticidal method of the present invention, as shown in the above-mentioned Examples, is a very simple control method from the viewpoint of excellent insecticidal action and work efficiency.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display area A01N 47/42

Claims (5)

[Claims] 1. A method for controlling harmful insects of fruits and vegetables,
At the time of planting the seedlings of the fruit and vegetables and / or after planting, a liquid preparation of the osmotic insecticidal compound is provided at the planting holes and / or the adjacent peripheral portions thereof, and at the plant origin of the flowering plants and / or the adjacent peripheral portions thereof. A pesticidal method characterized by applying. 2. The insecticidal compound is represented by the following formula: In the formula, R represents a hydrogen atom, acyl, alkyl or optionally substituted heteroarylalkyl, A represents a hydrogen atom, alkyl or a divalent group bonded to B, B represents alkyl, -S -R, Or a divalent group or atom bonded to A, wherein R is the same as defined above, Y is ═N— or Wherein T ¹ represents a hydrogen atom or an optionally substituted alkyl, and X represents an electron-withdrawing group. 3. The compound of formula (I) according to claim 2, wherein R is hydrogen atom, formyl, C _1-4 alkylcarbonyl,
Benzoyl, C _1-4 alkylsulfonyl, C _1-6 alkyl, or up to 6-membered optionally substituted heteroaryl having at least one N atom and optionally further having a heteroatom Represents methyl, where A is a hydrogen atom, C _1-6 alkyl, ethylene, trimethylene, or Wherein T ² is a hydrogen atom, C _1-4 alkyl or C
_{1-4 is} alkylcarbonyl, B is C _1-6 alkyl, —SR, embedded image -S-, methylene or Wherein R and T ² are as defined above, Y is = N- or = CH-, and X is nitro or cyano. 4. The compound of formula (I) according to claim 2, wherein R is hydrogen atom, formyl, acetyl, C _1-4 alkyl,
2-chloro-5-pyridylmethyl or 2-chloro-5-
Represents thiazolyl, wherein A is a hydrogen atom, C _1-4 alkyl, ethylene, trimethylene, or Wherein T ² is methyl or ethyl, B is C _1-4 alkyl, —SR, embedded image -S-, methylene or Are shown, wherein indicates the R and T ² are as defined above, Y is, = N-or = CH- indicates, and X is claim 1 or 2 insecticidal method where a nitro or cyano. 5. The compound of formula (I) according to claim 2, wherein R is 2-chloro-5-pyridylmethyl or 2-chloro-
5-thiazolylmethyl, wherein A is a hydrogen atom, C _1-4 alkyl, ethylene, trimethylene, or Wherein T ² is methyl or ethyl, B is C _1-4 alkyl, —SR, embedded image -S-, methylene or Wherein R and T ² are as defined above, Y is = N- or = CH-, and X is nitro or cyano.