JPH08245322A - Bactericidal/germicidal composition - Google Patents

Abstract

PURPOSE: To obtain the subject composition having high insecticidal/germicidal effect at low doses, capable of extending its residual effect, improved in labor saving and safety, thus useful for field crop, e.g. containing specific compound(s) and rice blast-controlling compound(s). CONSTITUTION: This insecticidal/germicidal composition contains (A) pref. 0.0001-50wt.% of at least one kind of compound of formula I (R1 is H or methyl; R2 -R4 are each H or a lower alkyl) such as 1- (tetrahydro-3-furanyl)methyl}-2- nitro-3-methylguanidine and (B) at least one kind of compound selected from diisopropyl-1,3-dithiolan-2-ylidene malonate, 5-methyl-1,2,4-triazolo[3,4- b][l,3]benzothiazole, cyclopropanecarboxamide derivatives of formula II (R8 is O or S; R9 -R11 are each H or a 1-5C lower alkyl), etc. The compound of formula I is a new substance.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel insecticidal and bactericidal composition exhibiting excellent insecticidal and bactericidal activity.

[0002]

The compound represented by the general formula (1) according to the present invention is a novel compound having an excellent insecticidal activity.

The isothiazolecarboxylic acid derivative represented by the general formula (2) is disclosed in JP-A-5-59024, and the cyclopropanecarboxamide derivative represented by the general formula (3) is disclosed in JP-A-62-201855. The publication describes that these derivatives have a rice blast control action.

Further, diisopropyl-1,3-dithiolane-2-ylidene malonate, 5-methyl-1,2,4
-Triazolo [3,4-b] [1,3] -benzothiazole, 3-allyloxy-1,2-benzothiazole-
1,1-dioxide, 4,5,6,7-tetrachlorophthalide, kasugamycin hydrochloride, O, O-diisopropyl-S-benzyl phosphorothioate (IBP), 1,
2,5,6-Tetrahydro-4H-pyrrolo (3,2,1
It is known that -ij) quinolin-4-one and O-ethyl-S, S-diphenyl phosphorodithioate (EDDP) also show a controlling effect against rice blast and the like.

However, the action of each of these active compounds is only one of the insecticidal effect and the bactericidal effect, and cannot control pests at the same time.

[0006]

Therefore, it has been desired to establish an agent for quickly and simultaneously controlling diseases and pests that occur at the same time.

[0007]

Means for Solving the Problems As a result of intensive studies to solve these problems, the present inventors have found that the general formula (1)
Containing at least one compound represented by diisopropyl-1,3-dithiolane-2-ylidene malonate, 5-methyl-1,2,4-triazolo [3,4]
-B] [1,3] -benzothiazole, 3-allyloxy-1,2-benzothiazole-1,1-dioxide,
4,5,6,7-tetrachlorophthalide, kasugamycin hydrochloride, O, O-diisopropyl-S-benzyl phosphorothioate (IBP), 1,2,5,6-tetrahydro-4H-pyrrolo (3,2,1 -Ij) Quinoline-4
-On, O-ethyl-S, S-diphenylphosphorodithioate (EDDP), an isothiazolecarboxylic acid derivative represented by the general formula (2), and a cyclopropanecarboxamide derivative represented by the general formula (3) A composition containing at least one selected compound shows not only excellent insecticidal and bactericidal effects against diseases and pests of paddy rice at the same time, but also when both compounds are mixed, the persistence of the insecticidal effect is particularly high. The present invention has been completed by also finding out that the number increases.

That is, the present invention is based on the general formula (1)

[0009]

[Chemical 4]

(Wherein R ₁ is a hydrogen atom or a methyl group,
R ₂ , R ₃ and R ₄ each represent a hydrogen atom or a lower alkyl group. ) At least one compound represented by the formula (1) and diisopropyl-1,3-dithiolane-2-ylidene malonate (hereinafter referred to as compound A),
5-methyl-1,2,4-triazolo [3,4-b]
[1,3] -Benzothiazole (hereinafter referred to as Compound B), 3-allyloxy-1,2-benzothiazole-
1,1-dioxide (hereinafter referred to as compound C), 4,5,
6,7-tetrachlorophthalide (hereinafter referred to as compound D), kasugamycin hydrochloride (hereinafter referred to as compound E),
O, O-diisopropyl-S-benzyl phosphorothioate (hereinafter referred to as compound F), 1,2,5,6-tetrahydro-4H-pyrrolo (3,2,1-ij) quinoline-
4-one (hereinafter referred to as compound G), O-ethyl-S, S
-From diphenyl phosphorodithioate (hereinafter referred to as compound H), an isothiazolecarboxylic acid derivative represented by the general formula (2) (chemical formula 5) and a cyclopropanecarboxamide derivative represented by the general formula (3) (chemical formula 6) An insecticidal and bactericidal composition comprising at least one selected compound.

[0011]

Embedded image

(In the formula, R ₅ is a hydrogen atom or a chlorine atom or a lower alkyl group having 1 to 5 carbon atoms, R ₆ is a hydrogen atom or a chlorine atom, and R ₇ is a linear or branched C 1 to 1 carbon atom.
Each of the 8 alkyl groups is represented. )

[0013]

[Chemical 6]

(In the formula, R ₈ is an oxygen atom or a sulfur atom,
R ₉ , R ₁₀ and R ₁₁ each represent a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms. )

A specific example of the isothiazolecarboxylic acid derivative represented by the general formula (2) is a compound of the following formula (Formula 7) (hereinafter referred to as compound I),

[0016]

[Chemical 7]

A specific example of the cyclopropanecarboxamide derivative represented by the general formula (3) is a compound represented by the following formula (Formula 8) (hereinafter referred to as compound J).

[0018]

Embedded image

The insecticidal and bactericidal composition of the present invention has no phytotoxicity to cultivated plants, has low toxicity to warm-blooded animals, and is highly safe. Moreover, since the seedling raising box treatment of the paddy rice using the insecticidal and bactericidal composition of the present invention can simultaneously control pests and diseases for a long period of time, it not only reduces the labor burden of farmers, but also reduces the amount of drug per unit area. And help reduce the impact on the environment. Furthermore, by mixing with fertilizer and performing lateral row fertilization at the time of rice planting or fixed planting, it is useful for further labor saving. Therefore, the insecticidal and bactericidal composition of the present invention is very effective for simultaneous control of pests and labor saving in agricultural crops and horticultural crops, and provides an outstanding technological advancement in industrial effectiveness.

The compound of the general formula (1) is a novel compound, and depending on the substituents, the following method (A) or (B):
It can be manufactured by the method.

Method (A): (reaction formula (1) (formula 9))

[0022]

[Chemical 9]

(Wherein R ₁ , R ₂ , R ₃ and R ₄ have the above-mentioned meanings, X ₁ is an amino group, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms or benzylthio. Represents a group.)

That is, the compound represented by the formula (2) is reacted with the compound represented by the formula (3) in various solvents in the presence of a base or a catalyst, if necessary, easily and in a high yield. It can be manufactured.

As the base, carbonates such as potassium carbonate and sodium carbonate, tripotassium phosphate, trisodium phosphate,
It is possible to use phosphates such as dipotassium monohydrogen phosphate and disodium monohydrogen phosphate, and acetates such as sodium acetate and potassium acetate.

As the catalyst, organic bases such as 4- (dimethylamino) pyridine, DBU, triethylamine, diazabicycloundecene, sulfonic acids such as p-toluenesulfonic acid and methanesulfonic acid, sulfuric acid, hydrogen chloride, phosphoric acid, etc. The mineral acids, ion exchange resins, silica gels, zeolites, etc. can be used.

Examples of the solvent include water, alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane, heptane and petroleum benzine, and dimethyl. Formamide, dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, aprotic polar solvent such as 1-methyl-2-pyrrolidinone, ethyl ether, diisopropyl ether, 1,2-dimethoxyethane, tetrahydrofuran, Ethers such as dioxane, nitriles such as acetonitrile and propionitrile, and ketones such as acetone and diisopropyl ketone can be used.

Although the reaction temperature and the reaction time can be varied over a wide range, the reaction temperature is generally -20 to 2
00 ° C, preferably 0-150 ° C, reaction time 0.01
~ 50 hours, preferably 0.1-15 hours.

The compound represented by the formula (2) in the reaction formula (1) can be produced by the method of the reaction formula (1A) (formula 10).

[0030]

[Chemical 10]

(In the formula, R ₁ and R ₂ have the above-mentioned meanings,
X ₂ represents a halogen atom, a toluenesulfonyloxy group, a methanesulfonyloxy group or a trifluoromethanesulfonyloxy group. )

That is, (tetrahydro-3-furanyl) methanol derivative is thionyl chloride, phosphorus oxychloride, phosphorus tribromide, triphenylphosphine / carbon tetrabromide, triphenylphosphine / carbon tetrachloride, etc. as a halogenating agent. A halide or tosyl chloride, methane sulfonyl chloride, trifluoromethane sulfonic acid anhydride or the like is converted into a sulfonate compound with a sulfonation agent, and then a known amine synthesis method such as the delpin method using hexamethylenetetramine, or alkylamines It can be produced by a reaction with.

The compound represented by the formula (3) in the reaction formula (1) can be prepared according to Chem. Ber. , Volume 100, page 591.

Method (B) In the formula (1), the formula (1a) in which R ₂ and R ₃ represent a hydrogen atom can be produced according to the reaction formula (2) (formula 11).

[0035]

[Chemical 11]

(Wherein R ₁ and R ₄ have the above-mentioned meanings,
R ₁₂ represents an alkyl group having 1 to 5 carbon atoms or a benzyl group. )

That is, the compound represented by the formula (4) can be easily produced in a high yield by reacting it in various solvents in the presence of an acid or, if necessary, a catalyst.

Acids or catalysts used include sulfonic acids such as p-toluenesulfonic acid and methanesulfonic acid,
Mineral acids such as sulfuric acid, hydrochloric acid and phosphoric acid, ion exchange resins, silica gels and zeolites can be used. As a solvent, water, alcohols such as methanol, ethanol, propanol, butanol, benzene, toluene, aromatic hydrocarbons such as xylene, hexane, heptane, aliphatic hydrocarbons such as petroleum benzine,
Aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, 1-methyl-2-pyrrolidinone, ethyl ether, diisopropyl ether,
Ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, nitriles such as acetonitrile and propionitrile, and ketones such as acetone and diisopropyl ketone can be used.

The reaction temperature and reaction time can be varied over a wide range, but in general, the reaction temperature is -20 to 1
50 ° C., preferably room temperature to 100 ° C., reaction time 0.0
It is 1 to 50 hours, preferably 0.1 to 10 hours.

The compound represented by the formula (4) in the reaction formula (2) can be produced by the method of the reaction formula (2A) (formula 12).

[0041]

[Chemical 12]

(In the formula, R ₁ and R ₄ have the above-mentioned meanings, X ₃ represents a chlorine atom, a bromine atom, a toluenesulfonyloxy group, a methanesulfonyloxy group and a trifluoromethanesulfonyloxy group, and R ₁₂ represents 1 to 5 carbon atoms
Represents an alkyl group or a benzyl group. )

That is, the compound represented by the formula (5) and the compound represented by the formula (6) are easily reacted with high yield in various solvents in the presence of a base or a catalyst, if necessary. It can be manufactured.

As the base, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride,
Alkali metal alcoholates such as sodium methylate and sodium ethylate, alkali metal oxides such as sodium oxide, carbonates such as potassium carbonate and sodium carbonate, tripotassium phosphate, trisodium phosphate, dipotassium dihydrogen phosphate, monophosphate Phosphates such as disodium hydrogen, acetates such as sodium acetate and potassium acetate, organic bases such as 4- (dimethylamino) pyridine, DBU, triethylamine and diazabicycloundecene can be used.

Examples of the solvent include water, alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane, heptane and petroleum benzine, and dimethyl. Formamide, dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, aprotic polar solvent such as 1-methyl-2-pyrrolidinone, ethyl ether, diisopropyl ether, 1,2-dimethoxyethane, tetrahydrofuran, Ethers such as dioxane, nitriles such as acetonitrile and propionitrile, and ketones such as acetone and diisopropyl ketone can be used.

The reaction temperature and reaction time can be varied over a wide range, but in general, the reaction temperature is -30 to 2
00 ° C, preferably -20 to 150 ° C, the reaction time is 0.
It is 01 to 50 hours, preferably 0.1 to 15 hours.

The compound represented by the formula (5) in the reaction formula (2A) is obtained by converting a (tetrahydro-3-furanyl) methanol derivative into thionyl chloride, phosphorus oxychloride, phosphorus tribromide, triphenylphosphine / tetraodor. It can be produced by halogenation with a halogenating agent such as carbon dioxide, triphenylphosphine / carbon tetrachloride or the like, or sulfonate with a sulfonation agent such as tosyl chloride, methanesulfonyl chloride or trifluoromethanesulfonic anhydride.

The compound represented by the formula (6) in the reaction formula (2A) can be produced from a monoalkyl-substituted nitroguanidine or a monobenzyl-substituted nitroguanidine, a primary amine and formaldehyde.

The insecticidal and bactericidal composition of the present invention exhibits an excellent insecticidal and bactericidal effect and exerts a proper controlling effect against harmful pests.

Examples of such pests include armyworm, rice armyworm, yellow-spotted moth, tamanaga moth, cotton grasshopper, velvetleaf moth, white-spotted sprouts, red-spotted sprouts, cabbage moth, yatoga, tamanagiuwawa,
Nikamaiga, Kobunomaiga, Sankamaiga, Nashiohingai, Himadaramaiga, Mamenomaiga, Rice Beetle, Cotton Bug, Potato Moth, Pieris brassicae,
Lepidoptera pests such as Nosima Madaraiga, Chanocha serrata, Astragalus oleracea, Mikanhamogiga, Grape Hosohamaki, Nashihime Shinkui, Mameshingaiga, Momoshiniga, Grape scabbard, Chanohosoga, Kogamu, Aedes albopictus, White-faced whitefly, White-faced whitefly, White-faced whitefly, White-faced whitefly, White-faced whitefly, White-faced whitefly Yukiyanagi aphid, apple aphid, green peach aphid, radish aphid, black radish aphid, bean aphid,
Citrus aphid, orange aphid, grape aphid, wheat aphid, potato aphid aphid, green tea leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper, leafhopper leafhopper , San Jose scale insect, apple scale scale, red scale scale, red scale scale scale, jade scale scale, stag beetle scale, citrus scale scale, iseria scale scale,
Hemiptera pests such as apple psyllid, orange psyllid, southern green bug, beetle bug, nasi gumbai, etc .;
Rice weevil, rice beetle, beetle beetle, Colorado potato beetle, beetle beetle, Diabrotica
spp., Weevil, Black weevil, Black weevil, Lady bean weevil, Azuki bean weevils, Leaf beetle weevil, Rhus scutellariae, Poison beetle, Beetle beetle, Helicopterum vulgaris, Pleurotus sp. Diptera such as Chica mosquito, Chinese mosquito, Aedes albopictus, Aedes albopictus, Soybean fly, Rice fly, Rice flesh fly, house fly, black fly, onion fly, urchin fly, citrus fruit fly; Negia thrips,
Thrips thrips insects such as Kakida thrips, Southern thrips, rice thrips, tea thrips; black cockroaches, cockroaches, american cockroaches,
Orthoptera pests such as German cockroaches, Red-faced locusts, and locusts; Hymenoptera pests such as wasps
Pests of the order Acarina, such as house dust mites, chiggers, and mites; other fleas, head lice, mountain termites,
Examples include burned millipede and gudgeon.

Examples of such diseases include blast fungus ( Pyricularia 0ryzae ) and the like.

When the insecticidal and bactericidal composition of the present invention is actually applied, it may be a mixture of the above-mentioned two components or a single conventional formulation for mixing them in situ. In formulating the insecticidal bactericidal composition of the present invention,
Emulsions, wettable powders, powders, granules, fine granules, flowables, microcapsules, oils, aerosols, smoke, etc. according to common agricultural chemicals without any special conditions. It can be adjusted to an arbitrary dosage form such as an agent, a poison bait, etc., and these can be used for various purposes according to respective purposes.

The term "carrier" as used herein refers to the synthesis or synthesis of a liquid, solid or gas which is formulated to help the active ingredient reach the site to be treated and facilitate the storage, transportation and handling of the active ingredient compound. It means a natural inorganic or organic substance.

Examples of suitable solid carriers include montmorillonite, kaolinite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel,
Inorganic substances such as ammonium sulfate, soybean flour, sawdust, wheat flour, pectin,
Methylcellulose, sodium alginate, petrolatum,
Examples include organic substances such as lanolin, liquid paraffin, lard, and vegetable oil.

Suitable liquid carriers include, for example, toluene,
Aromatic hydrocarbons such as xylene, cumene and solvent naphtha, paraffin hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, ketones such as acetone, methyl ethyl ketone and cyclohexanone, Ethers such as dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc., esters such as ethyl acetate, acetic acid butyl ester, fatty acid glycerin ester, etc. acetonitrile, nitriles such as propionitrile Alcohols such as methanol, ethanol, n-propanol, isopropanol, ethylene glycol, dimethylformamide, di- Sulfoxide, water and the like.

Further, in order to enhance the efficacy of the insecticidal and bactericidal composition of the present invention, the following auxiliary agents may be used alone or in combination depending on the purpose, taking into consideration the dosage form of the preparation, the application scene and the like. It can also be used.

As auxiliary agents used for the purpose of emulsification, dispersion, spreading, wetting, binding, stabilization, etc., water-soluble bases such as lignin sulfonates, alkylbenzene sulfonates,
Alkyl sulfates, polyoxyethylene alkylaryl ethers, nonionic surfactants such as polyhydric alcohol esters, lubricants such as calcium stearate and wax, stabilizers such as isopropylhydrodiene phosphate, other methyl cellulose, carboxymethyl cellulose, Examples include casein and gum arabic.
However, these components are not limited to those described above.

The insecticidal and bactericidal composition of the present invention contains light, heat,
It is stable against oxidation and the like, but if necessary, an antioxidant or an ultraviolet absorber, for example, a phenol derivative such as BHT (2,6-di-t-butyl-4-methylphenol), BHA (butylhydroxyanisole), A bisphenol derivative, arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, and a condensation product of phenetidine and acetone, or benzophenone compounds are added in appropriate amounts as stabilizers to obtain a more effective and stable composition. You can

The insecticidal active compound represented by the formula (1) and the fungicidal active compound used in the insecticidal and fungicidal composition of the present invention are 0.0000001 to 95% by weight, respectively.
Preferably 0.0001 to 50% by weight is contained. To apply the insecticidal and bactericidal composition of the present invention, generally 0.001 to 5000 ppm of the active ingredient, preferably 0.01 to 1
It is desirable to use it at a concentration of 000 ppm. Also, 1
The amount applied per 0a is generally 1 to 300 g of the active ingredient.
Is.

[0060]

EXAMPLES Next, the insecticidal and bactericidal composition of the present invention will be specifically described with reference to production examples and formulation examples. Production Example 1 1-{(tetrahydro-3-furanyl) methyl} -2-nitro-3-methylguanidine (Compound N
o. 1) Preparation of (tetrahydro-3-furanyl) methanol 10.0
g, anhydrous trifluoromethanesulfonic acid 29.5 g, pyridine 10.0 g, and dichloromethane 200 ml were stirred at room temperature for 1 hour. Water was poured into the reaction solution, the organic layer was separated, washed with 1N hydrochloric acid, water and saturated brine, dried and concentrated to obtain 20.0 g of 3-tetrahydrofuranylmethyl triflate. 1,5-Dimethyl-2-nitroiminohexahydro-1,3,5-triazine 12.5 g, DMF
3.25 g of 60% sodium hydride at room temperature in 60 ml
Was added and stirred for 1 hour, 20.0 g of 3-tetrahydrofuranylmethyl triflate was added at room temperature, and the mixture was stirred at 50 ° C. for 2 hours. After cooling to room temperature, add 50 ml of 2N hydrochloric acid,
The mixture was stirred at 50 ° C for 2 hours. After neutralization with sodium bicarbonate, extraction with dichloromethane, drying and concentration, the residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate: hexane =
1: 1) and 7.8 g of 1-{(tetrahydro-
3-furanyl) methyl} -2-nitro-3-methylguanidine was obtained.

Production Example 2 Production of N-{(tetrahydro-3-furanyl) methyl} -N- (methyl) nitroguanidine (Compound No. 3) (Tetrahydro-3-furanyl) methyl tosylate 0,
71 g, sodium iodide 0.08 g, potassium carbonate 0.85 g, 40% methylamine methanol solution 9 ml
The mixture was heated to reflux for 5 hours. The insoluble material was filtered off, and the reaction solution was concentrated under reduced pressure to obtain crude N-{(tetrahydro-3-
To furanyl) methyl} -N-methylamine, 0.38 g of S-methyl-N- (nitro) isothiourea and 7 ml of acetonitrile were added, and the mixture was heated under reflux for 5 hours. The reaction solution was concentrated under reduced pressure, purified by silica gel column chromatography (developing solvent; ethyl acetate: hexane = 1: 1),
10 g of N-{(tetrahydro-3-furanyl) methyl} -N- (methyl) nitroguanidine was obtained.

Production Example 3 Production of 1-{(tetrahydro-3-furanyl) methyl} -1-ethyl-2-nitro-3-methylguanidine (Compound No. 4) N-{(tetrahydro-3-furanyl) methyl } -N-
5.5 g of ethylamine and S-methyl-N-nitro-N '
-Methylisothiourea 3.0 g, ethanol 30 m
A mixture of 1 and DMAP 0.5 g was heated under reflux for 4 hours. Then, the reaction solution was concentrated under reduced pressure, and the obtained crude oily substance was purified by column chromatography. 1-{(tetrahydro-3-furanyl) methyl} -1-ethyl-2
1.1 g of -nitro-3-methylguanidine was obtained.

Production Example 4 N- [4-{(2-methyl) tetrahydrofuranyl} methyl] -N'-methyl-N "-
Production of nitroguanidine (Compound No. 5) 2-methyl-4-hydroxymethyltetrahydrofuran 1.00 g and triethylamine 1.05 g in a dichloromethane 50 ml solution under ice-cooling trifluoromethanesulfonic anhydride 2.91 g dichloromethane 10 ml
The solution was added dropwise over 5 minutes. The reaction solution was stirred under ice-cooling for 30 minutes and at room temperature for 5 hours, and then the reaction solution was concentrated under reduced pressure to give an oily product, which was sodium hydride (about 60%).
To a suspension of 32 g of dimethylformamide in 5 ml of 1-methyl-2-nitroimino-5-methyl-1,
A solution of 1.24 g of 3,5-triazine in 5 ml of dimethylformamide was added, and the mixture was stirred at 60 ° C. for 30 minutes, and then added as a 5 ml solution of dimethylformamide at room temperature, and stirred at 60 ° C. for 4 hours. Hydrochloric acid (2M) in the reaction solution
7.2 ml was added, and the mixture was further stirred at 60 ° C. for 3 hours.
The reaction solution was allowed to cool to room temperature, ethyl acetate was added, this was washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The oily substance obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography (developing solvent; ethyl acetate) to give N- [4-{(2-methyl) tetrahydrofuranyl} methyl] -N'-. Methyl-
77 mg of N "-nitroguanidine were obtained as a reddish brown oil.

The physical properties of the compound represented by the general formula (1) obtained according to Production Examples 1 to 4 are shown in Table 1 (Tables 1 and 2).
Shown in

[0065]

[Table 1]

[0066]

[Table 2]

Formulation Example 1 10 parts of compound 5, 40 parts of compound F, SOLPOL 35
5S (Toho Chemical, surfactant) 10 parts, xylene 40
The above parts and the above were uniformly mixed with stirring to obtain an emulsion. In addition, a part represents a weight part.

Formulation Example 2 10 parts of compound 4, 25 parts of compound C, 2 parts of sodium alkylnaphthalene sulfonate, 1 part of sodium lignin sulfonate, 5 parts of white carbon, diatomaceous earth 57
Parts and the above were uniformly mixed with stirring to obtain 100 parts of a wettable powder.

Formulation Example 3 0.3 part of compound 3, 1 part of compound B and 0.3 part of white carbon are uniformly mixed, and 98.2 parts of clay and 0.2 part of doliles A (manufactured by Sankyo) are added. And uniformly pulverized and mixed to obtain 100 parts of powder.

Formulation Example 4 2 parts of compound 1, 2 parts of compound I, white carbon 2
Parts, 2 parts of sodium lignin sulfonate, 82 parts of bentonite, after uniformly pulverizing and mixing the above, water is added and kneaded,
The mixture was granulated and dried to obtain 100 parts of granules.

Formulation Example 5 2 parts of compound 1, 2 parts of compound, 2 parts of white carbon
Parts, 2 parts of sodium lignin sulfonate, 82 parts of bentonite, after uniformly pulverizing and mixing the above, water is added and kneaded,
The mixture was granulated and dried to obtain 100 parts of granules.

Formulation Example 6 10 parts of compound 2, 40 parts of compound F and 5 parts of a 20% aqueous solution of polyvinyl alcohol were thoroughly mixed with stirring,
45 parts of a 0.8% aqueous solution of xanthan gum was added and mixed again with stirring to obtain 100 parts of a flowable agent.

Test Example 1 An emulsion prepared in accordance with Formulation Example 1 was used as an aqueous solution having a predetermined concentration, and 100 ml per 3 pots was added to a paddy rice (cultivar: Koshihikari) in which 5 strains were planted in a Wagner pot (1/5000 are), 3 plants each. Sprayed. The next day, a spore suspension of rice blast fungus was spray-inoculated and cultivated under high humidity conditions.
The number of diseased groups was investigated on the day and the 20th day. The control rate was calculated by the following formula (Equation 1).

[0074]

[Equation 1]

10 and 20 days after the spraying, the paddy rice was covered with a wire netting cylinder, and 10 female adults of the flying stalker planthopper were released inside, and the mortality rate was examined 48 hours later. The results are shown in Table 2 (Table 3).

[0076]

[Table 3]

Test Example 2 Granules prepared according to Formulation Example 4 were weighed in predetermined amounts and applied to the water surface of paddy rice (cultivar: Koshihikari) in which 5 strains were planted in a Wagner pot (1/5000 are), 3 plants each in 3 plants. . Five days later, a spore suspension of rice blast fungus was spray-inoculated, cultivated under high humidity conditions, and the number of diseased spots was examined 10 and 20 days after the drug treatment. The control rate was calculated in the same manner as in Test Example 1. In addition, 10 and 20 days after the treatment, the paddy rice was covered with a wire netting cylinder, 10 adult females of the planthopper plant were released into the interior, and the mortality rate was examined 48 hours later. The results are shown in Table 3 (Table 4).

[0078]

[Table 4]

Test Example 3 50 g of each of the granules prepared according to Formulation Example 4 was treated in a seedling raising box of paddy rice (cultivar: Koshihikari), and 5 plants were planted in a Wagner pot (1/5000 are) on the next day, 3 plants each. did. The next day, a spore suspension of rice blast fungus was spray-inoculated, cultivated under high humidity conditions, and the number of diseased spots was examined 10 and 20 days after planting. The control rate was calculated in the same manner as in Test Example 1. Also, 10 and 20 days after planting, the paddy rice was covered with a wire net cylinder, and 10 adult females of the brown planthopper were released inside,
The mortality was investigated 48 hours later. The results are shown in Table 4 (Table 5).
It was shown to.

[0080]

[Table 5]

Test Example 4 50 g of each of the granules prepared according to Formulation Example 4 was treated in a nursery box of paddy rice (cultivar: Koshihikari), and 5 strains of each 3 plants were planted in a Wagner pot (1/5000 are) on the next day. did. 20, 40, 60 and 80 days after planting, the paddy rice was covered with a wire netting cylinder, and 10 female adults of the brown planthopper were released inside, and the mortality rate was examined 48 hours later. In addition, drug damage was also investigated at the same time. The results are shown in Table 5 (Table 6).

[0082]

[Table 6]

[0083]

EFFECTS OF THE INVENTION The insecticidal and bactericidal composition of the present invention has excellent insecticidal and bactericidal effects, as is clear from the above test results, is very useful for simultaneous control of pests and diseases, and the number of times of application and application of agricultural chemicals. The dose can be reduced. Further, the insecticidal and bactericidal composition of the present invention can prolong the residual effect of the insecticide as compared with the case of using the insecticide alone. Therefore, the insecticidal and bactericidal composition of the present invention can greatly contribute to labor saving of agriculture and protection of the environment.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical indication location A01N 43:78) (72) Inventor Kenji Otaka 1144, Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd. In the company

Claims (1)

[Claims] 1. A compound represented by the general formula (1): (Wherein R ₁ represents a hydrogen atom or a methyl group, and R ₂ , R ₃ and R ₄ represent a hydrogen atom or a lower alkyl group, respectively) and at least one compound is contained,
And diisopropyl-1,3-dithiolane-2-ylidene malonate, 5-methyl-1,2,4-triazolo [3,4-b] [1,3] -benzothiazole, 3-allyloxy-1, 2-benzothiazole-1,1-dioxide, 4,5,6,7-tetrachlorophthalide, kasugamycin hydrochloride, O, O-diisopropyl-S-benzyl phosphorothioate (IBP), 1,2,5,6-
Tetrahydro-4H-pyrrolo (3,2,1-ij) quinolin-4-one, O-ethyl-S, S-diphenyl phosphorodithioate (EDDP), general formula (2)
An insecticidal and bactericidal composition comprising at least one compound selected from the isothiazolecarboxylic acid derivative represented by the formula (1) and the cyclopropanecarboxamide derivative represented by the general formula (3) (formula 3). Embedded image (In the formula, R ₅ is a hydrogen atom, a chlorine atom or a carbon number 1
To R 5 are lower alkyl groups, R ₆ is a hydrogen atom or a chlorine atom, and R ₇ is a linear or branched C 1-18 alkyl group. ) [Chemical 3] (In the formula, R ₈ represents an oxygen atom or a sulfur atom, and R ₉ , R ₁₀ and R ₁₁ represent a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms.)