JPH03279359A - Nitroguanidine derivative, its production and pest controlling agent containing same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R<1>, R<2> and R<3> are each H, alkyl or acyl; when one of R<1>, R<2> and R<3> is acyl, the other two are each H or alkyl) and its salt. EXAMPLE:1-(6-Chloro-3-pyridylmethyl)-1-methyl-2-nitroguanidine. USE:Useful for pest controlling agents. Active for plant parasitic mites such as Two-spotted spider mite, agricultural insect pests such as Diamond-back moth, sanitary insect pests such as Ornithonyssus bacoti, stored grain insect pests such as Auguimois grain moth, clothing and house insect pests such as Tinea pellionella, etc. Also having excellent penetrativity, thus effective for soil treatment. PREPARATION:The objective compound of the formula I can be obtained by reaction between a compound of formula II (R<1> and R<2> are each H, alkyl or acyl, being not acyl at the same time) and a second compound of formula III (R<3> is H, acyl or alkyl; when one of R<1> and R<2> is acyl, R<3> is H or alkyl).

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to novel nitroguanidine derivatives, methods for producing them, and pest control agents containing them.

(Prior art and background to the invention) 1-nitro-2,2-diaminoethylene derivatives are disclosed in JP-A-64-70468, JP-A-2-171, etc.
Cyanoguanidine derivatives are disclosed in JP-A-64-47766 and JP-A-64-70467, and JP-A-64-63
No. 156786 discloses that 2-nitroiminoimidazolidine derivatives are useful as active ingredients of insecticides and the like. However, there is a general formula (
The nitroguanidine derivatives of the invention represented by I) are not disclosed.

(Disclosure of the Invention) The present invention relates to a nitroguanidine derivative represented by the following general formula (I) or a salt thereof, a method for producing them, and a pest control agent containing them.

General formula (I) (wherein R1, RZ and R3 are each independently a hydrogen atom, an alkyl group or an acyl group, provided that RI, R
and R3 is an acyl group, the other two are a hydrogen atom or an alkyl group) In the general formula (I), RI, R! The alkyl group represented by RIR2 and R3 includes those having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc., and the acyl group represented by RIR2 and R3 includes formyl group, Group; acetyl group, propionyl group, butyryl group,
Examples include alkylcarbonyl groups such as valeryl group and hexanoyl group; benzoyl group, and the above-mentioned alkyl groups and alkylcarbonyl groups also include those having structural isomerism such as linear or branched aliphatic chains.

Examples of the salt of the compound represented by the general formula (I) include salts with acidic substances, such as inorganic acid salts such as hydrochloride, hydrobromide, phosphate, sulfate, and nitrate. can be mentioned.

The compound represented by the general formula (I) has E-isomer and 2-isomers, and the present invention also includes E-isomer, 2-isomer and mixtures thereof.

The present invention also includes compounds that exhibit a tautomer represented by 1 NO□ \/ 2 when at least one of R1, R'' or R3 in the general formula (I) is a hydrogen atom.

The compound represented by the general formula (I) can be produced, for example, by the method of the following reaction step a.

[Reaction step a]

No.

/NO□/(I) (In the formula, R1, R2 and R3 are as described above) Reaction step a is usually carried out in the presence of a solvent.

Examples of the solvent include water; alcohols such as methanol, ethanol, propatool, isoproptool, butanol, and t-butanol; dimethylformamide;
aprotic polar solvents such as dimethyl sulfoxide;
These can also be used in combination.

The reaction temperature in reaction step a is usually 30 to 150°C, preferably 50 to 100°C, and the reaction time is 1 to 24 hours, preferably 2 to 12 hours.

In the general formula (I), one of R1 and R2 is a hydrogen atom, the other is an alkyl group or an acyl group, and R3 is an alkyl group or an acyl group. It can also be produced by a method.

[Reaction step b]

NO□ / 4 (I-1) (IV) NO□ / (wherein, R4 and R5 are each independently an alkyl group or an acyl group, and X is a leaving group, provided that when R4 is an acyl group, (R5 is not an acyl group) In the general formula (IV), the leaving group represented by is an alkyl group or a phenyl group).

The reaction steps are usually carried out in the presence of a base and a solvent.

Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; tertiary amines such as triethylamine; and pyridine. Examples of the solvent include aprotic polar solvents such as acetonitrile, dimethylformamide, and dimethyl sulfoxide, and two or more of these solvents can be used in combination. The reaction temperature in the reaction step is usually -30 to 80°C, preferably 0 to 30°C.
℃, and the reaction time is 0.5 to 24 hours, preferably 1
~12 hours.

In addition, the amount of the compound represented by the general formula (I-1) and the compound represented by the general formula (mV) used as raw materials for the reaction step is based on 1 mole of the compound represented by the general formula (I-1).
The amount of the compound represented by formula (IV) is 0.9 to 1.2 mol.

Further, the compound represented by the general formula (I-1) also includes tautomers as described above.

In the general formula (I), a compound in which R' and R2 simultaneously have the same alkyl group and R3 is an alkyl group or an acyl group can also be produced, for example, by the method of the following reaction step C. .

[Reaction step C]

O2 / 4 (I-1) (V) NO□ / (wherein R4 and X are as described above, and R6 is an alkyl group) Reaction step C is usually carried out in the presence of a base and a solvent.

As the base and solvent, the same bases and solvents as those used in the above reaction steps can be mentioned. Further, the reaction temperature and reaction time of reaction step C are also the same as those of the above reaction step.

In addition, the amount of the compound represented by the general formula (I-1) and the compound represented by the general formula (V) used as the raw materials for reaction step C is as follows: The amount of the compound represented by formula (V) is 1.8 mol or more.

Next, a specific example of synthesis of the compound of the present invention will be described.

Synthesis Example 1 Synthesis of l-(6-chloro-3-pyridylmethyl)-1-methyl-2-nitroguanidine (compound 1lkL1) N,S-dimethyl-N'-nitroisothiourea 2,46
g and N-(6-chloro-3-pyridylmethyl)-N-
2.85 g of methylamine and 15IIll of ethanol
After adding to the solution, the mixture was reacted under reflux for 12 hours. After the reaction is completed, the reaction solution is cooled, and the precipitated crystals are collected by filtration and washed with cold ethanol to obtain a melting point of 156.7-157.
2.1 g of the target product (compound group 1) was obtained at 2°C.

Synthesis Example 2 l-(6-chloro-3-pyridylmethyl)-1,3,3
-) riftyl-2-nitro-guanidine (compound number 2)
Synthesis of ■-(6-chloro-3-pyridylmethyl)-1-methyl-2-nitro-guanidine (obtained in Synthesis Example 1 above)
Compound Nctl) 1.0g was dissolved in dimethylformamide 10
After dissolving in mA, 0.34 g of sodium hydride (60% oil suspension) was gradually added thereto while cooling with water. After the generation of hydrogen gas has finished, add 0.5 mff of methyl iodide.
1 was gradually added dropwise under water cooling. After finishing dropping,
The solution temperature was returned to room temperature, and stirring was continued for an additional 2 hours.

After the reaction was completed, dimethylformamide was distilled off under reduced pressure, and ethyl acetate and water were added to the residue for extraction.

After drying the organic layer over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure, and the resulting residue was subjected to silica gel chromatography (eluent: ethyl acetate/methanol-85
/15), the refractive index nD' is 1.5.
0.22 g of the target compound 819 (compound number 2) was obtained.

Next, representative examples of the compounds represented by the general formula (I) are listed in Table 1.

Below is the blank Table O2 / NMR spectrum data of compound 6' II-NMR (CDC et al.): δ = 2.23 (
s, 3H, COCll5); 3.00 (s
, 3H, NCHs); 4.70 (s,
2H, C11z); 7.30 (d, III,
J=7.811z); 7.74 (d, Ill
, J-7,811z) ;8.30 (d,
IH, J-2,0Hz) ;9.80 (broa
d, IH) The compound of the present invention exhibits excellent activity as an active ingredient of a pest control agent.

For example, two-spotted spider mite, false two-spotted spider mite, orange spider mite,
Plant-parasitic mites such as bed mites, mealybugs, armyworms, fall armyworms, codling moths, ballworms, tobacco budworms, gypsy moths, Colorado potato beetles, cucumber beetles, poleweevils, aphids, planthoppers,
Agricultural pests such as leafhoppers, scale insects, stink bugs, whiteflies, thrips, grasshoppers, wasp flies, scarab beetles, ants, etc., hygiene such as dust mites, cockroaches, houseflies, Culex mosquitoes, etc. Pests, grain storage pests such as bur moths, adzuki bean weevils, small bean weevils, mealworms, etc., clothing and house pests such as burs, burrs, termites, etc., fleas that parasitize livestock, etc.
It is effective against lice, flies, etc., and is also effective against plant parasitic mites such as cat nematodes, cyst nematodes, white nematodes, rice nematodes, strawberry nematodes, pine tree nematodes, etc. It is also effective for types. It is also effective against soil pests. The soil pests mentioned here include slugs,
Examples include gastropods such as the gypsy snail, and isopods such as pill bugs and woodlice. Furthermore, it is effective against pests such as Dicobol (trade name: Narita Pharmaceutical Co., Ltd.), plant parasitic mites that are resistant to organophosphorus agents, aphids that are resistant to organophosphorus agents, and house flies. Furthermore, since the compound of the present invention has excellent permeability, the compound of the present invention can be applied to soil to eliminate harmful insects from the soil.
In addition to controlling mites, nematodes, gastropods, and isopods, it can also control pests on leaves and stems.

When using the compound of the present invention as an active ingredient of a pest control agent, it can be used in combination with agricultural chemical adjuvants such as emulsions, powders, granules, wettable powders, liquids, aerosols, pastes, etc., as in the case of conventional pesticide formulations. It can be formulated into various forms. The mixing ratio of these ingredients is usually 0.5 to 90 parts by weight of the active ingredient and 10 to 99.5 parts by weight of the pesticide auxiliary. When actually using these preparations, either use them as is or
Alternatively, it can be used after being diluted to a predetermined concentration with a diluent such as water.

The agrochemical auxiliaries mentioned here include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrating agents, wetting agents, thickeners, stabilizers, etc., and may be added as appropriate if necessary. They are divided into solid carriers and liquid carriers. Solid carriers include starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, animal and vegetable powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, and diatomaceous earth. Examples of liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, ketones such as acetone and methyl ethyl ketone, dioxane,
Ethers such as tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane and solvent naphtha, halogenated hydrocarbons such as chloroform and chlorohenzene, dimethyl Examples include acid amides such as formamide, esters such as ethyl acetate and glycerin esters of fatty acids, nitriles such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide.

In addition, other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides,
It can be mixed or used in combination with plant growth regulators, etc., and may exhibit even better effects in this case.

For example, as an insecticide, acaricide, or nematicide,
O-(4-bromo-2-chlorophenyl)〇-ethyl S
-propyl phosphorothioate, 2,2-dichlorovinyl, dimethyl phosphate, ethyl 3-methyl-4-(
Methylthio) phenylisopropyl phosphoroamidate, 0.0-dimethyl 0-4-nitro-m-)lyl phosphorothioate, 0-ethyl 0-4-nitrophenylphenyl phosphonothioate, 0,0-diethyl 0-2-isopropyl -6-Methylpyrimidin-4-yl phosphorothioate, 0.0-dimethyl O-(3,5,6-dolichloro-2-pyridyl)phosphorothioate, 0,S-
Dimethylacetylphosphoramidothioate, O-(2
, 4-dichlorophenyl) O-ethyl S-propyl phosphorodithioate;
(Methylthio)propionaldehyde O-methylcarbamoyloxime, 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethylcarbamate, dimethyl N,N'-[thiobis[(methylimino)carbonyloxy)]bisethanimidothio ate, S-methyl N-(methylcarbamoyloxy)thioacetimidate, N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-(ethylthiomethyl)phenylmethylcarbamate, 2- Carbamate compounds such as dimethylamino-5,6-dimethylpyrimidin-4-yldimethylcarbamate, S,S-2-dimethylaminotrimethylenebis(thiocarbament); 2,2.2-)dichloro-1 ，
Organochlorine compounds such as 1-bis(4-chlorophenyl)ethanol and 4-chlorophenyl-2,4,5-1-dichlorophenylsulfone; Organometallic compounds such as tricyclohexyltine hydroxide; (R5)-α
-cyano-3-phenoxybenzyl (RS) 2-(4-
chlorophenyl)-3-methylbutyrate, 3-phenoxybenzyl (IRS) -cis, trans-3-(
2,2-dichlorovinyl) -2,2 dimethylcyclopropanecarboxylate, (RS) α-cyano-3-phenoxybenzyl (IRS) cis, trans-3-(2
,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 1-1(S) -α-cyano-3
-phenoxybenzyl(IR)-cis-3-(2,2-
dibromovinyl)-22-dimethylcyclopropanecarboxylate, (RS)-α-cyano-3-phenoxybenzyl (IR5)-cis, trans-3-(2-chloro-3,3,3-trifluoropropenyl)- 2,2-
Dimethylcyclopropanecarboxylate, 4-methyl-235,6-titrafluorohendyro-3-(2-chloro-3,3,3-trifluoro-1-propen-1yl)-2,2-dimethylcyclopropanecarboxylate Pyrethroid compounds such as acids; 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea, 1
-(3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-3-
(2,6-difluorobenzoyl)urea, 1-(3,
5-dichloro-2,4-difluorophenyl)-3-(
Benzoylurea compounds such as 2,6-difluorobenzoyl)urea; 2-tert-butylimino-3
-isopropyl-5-phenyl-3,4,5,6-titrahythro2H-L3,5-thiadiazin-4-one, trans-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo Compounds such as thiazolidinone 3-carboxamide, N-methylbis(2,4-xylyliminomethyl)amine; isopropyl (2E,
4E)-11-methoxy3.7.11-trimethyl-
Juvenile hormone-like compounds such as 2,4-dodecagenoate; other compounds include dinitro compounds, organic sulfur compounds, urea compounds, and triazine compounds. Furthermore, it can be mixed or used in combination with microbial pesticides such as BT agents and insect pathogenic virus agents.

For example, fungicides include S-benzyl-〇,〇-diisopropyl, phosphorothioate, 0-ethyl, S,
- Organophosphorus compounds such as diphenylphosphorodithioate, aluminum ethyl hydrogen phosphonate, organochlorine compounds such as 4,5,6,7-titrachlorophthalide, tetrachloroisophthalonitrile; Manganese ethylene bis( dithiocarbamate), zinc ethylene bis(dithiocarbamate), zinc and maneb complex, didizinc bis(dimethyldithiocarbamate), ethylene bis(dithiocarbamate), zinc propylene bis(dithiocarbamate), etc. dithiocarbamate type compound; 3
a, 4,7.7a-tetrahydro-N-(trichloromethylsulfenyl)phthalimide, 3a, 4.7.7a
N-halogenothioalkyl compounds such as -tetrahydro-N-(I,1,2,2-tetrachloroethylsulfenyl)phthalimide, N-()dichloromethylsulfenyl)phthalimide; 3-(3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide, (R3) -3-(3,
5-dichlorophenyl)-5-methyl-5-vinyl-1
, 3-oxazolidine-2,4-dione, N-(3,5
Dicarboximide compounds such as -dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide; methyl 1-(butylcarbamoyl)benzimidazole-2-yl-bamate, dimethyl 4.4
Benzimidazole compounds such as -(o-phenylene)bis(3-thioallophanate); 1-(4-chlorophenoxy)-3,3-dimethyl-1-(I H-
1,2,4-triazol-1yl)butanone, 1-(
biphenyyl-4-yloxy)-3,3-dimethyl-
1-(I H-L2゜4-triazol-1-yl)butan-2-ol, 1-(N-(4-chloro-2-trifluoromethylphenyl)-2-propoxyacetimidoylcoimidazole, 1 -[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolane-2
-ylmethyl)-1H-1,2,4-)riazole,
1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl) -1)
(-1,2,4-1-riazole, 1-[2-(2,4
-dichlorophenyl)pentyl)-1H-1,2,4-
Azole compounds such as triazole; 2,4′-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, (±)-2,4′-difluoroα-(
I H-1,2,4-)riazol-1-ylmethyl)
Carbinol compounds such as benzhydryl alcohol; 3'-isopropoxy-o-)rianilide, α, α
, benzanilide-based compounds such as α-trifluoro-3′-isopropoxy-〇-)-methyl N-
(2methoxyacetyl)-N-(2,6-xylyl)-
Phenylamide compounds such as DL-alaninate;
3-chloro-N-(3-chloro-2,6-sinitro 4
- Pyridinamines such as α, α, α-trifluorotolyl) 5-trifluoromethyl-2-pyridinamine; Other compounds include piperazine-based compounds, morpholine-based compounds, anthraquinone-based compounds, quinoxaline-based compounds, and crotons. Examples include acid compounds, sulfenic acid compounds, urea compounds, and antibiotics.

When applying the pest control agent of the present invention, -C is 1 to 20,
The concentration of the active ingredient is preferably 20 to 2,000 ppm, but the concentration of the active ingredient can be changed as appropriate depending on the form of the preparation, the method of application, the purpose, the timing, the location, the pest infestation situation, etc. For example, in the case of harmful aquatic insects, the concentration range of the active ingredient in water is below the above range, since it is possible to control aquatic pests by spraying a chemical solution with the above concentration range to the place of occurrence. The application amount per unit area is about 0.1 to 5,000 g, preferably 10 to 1,000 g of the active ingredient compound per 10 acres. However, in special cases it is also possible to depart from these ranges.

The various formulations containing the compounds of the present invention or their dilutions can be applied by commonly used application methods, i.e., spreading (e.g., scattering, spraying, misting, atomizing, dusting, water surface application, etc.), soil application, etc. (contamination, irrigation, etc.)
It can be carried out by surface application (painting, powder coating, coating, etc.), immersion of poison bait, etc. It is also possible to feed the above-mentioned active ingredient to livestock by mixing it with their feed to control the emergence and growth of harmful insects, particularly harmful insects, in their excrement. In addition, the so-called ultra-high concentration small volume spraying method (ultra low volume spraying method)
It can also be applied by me). In this way, 100% active ingredient content is possible.

Rice seedlings were immersed in a chemical solution adjusted to have an active ingredient concentration of 800 ppm for about 10 seconds, and after air-drying, the roots were wrapped with moist absorbent cotton and placed in a test tube. Next, 10 larvae of the brown planthopper were released into the tube, the mouth of the tube was covered with gauze, and the temperature was kept at 26°C.
It was left in a thermostat with lighting. The survival rate was determined by the following formula.

Compounds 1.2, 4.6 and 8 showed 100% mortality.

2. The test was conducted in the same manner as in Test Example 1 above, except that the larvae of the black-spotted leafhopper were replaced with the larvae of the black-spotted leafhopper, and the mortality rate was determined.

Compounds 1.2.4.6.7 and 8 showed 100% mortality.

3. Each formulation of green peach aphid active ingredient compound was dispersed in water and the concentration was adjusted to 800 ppm. An eggplant with only one leaf left was transplanted into a cup (diameter 8 an, height 7 cm), inoculated with 2 to 3 wingless viviparous female adult green peach aphids, and pups were produced. Two days after inoculation, the adults were removed and the number of larvae was counted. The eggplant leaves infested with larvae were immersed in a chemical solution adjusted to the above-mentioned concentration for about 10 seconds, air-dried, and then left in an illuminated incubator at 26°C. The survival rate was determined by the following formula. In addition, detached insects were considered to be dead.

Compounds 1.2.4.6.7 and 8 showed 100% mortality.

4 Green Peach Fly Insect' Each formulation of the active ingredient compound was dispersed in water, and the concentration was adjusted to 800 ppm. Transplant the eggplant leaves with only one leaf left into a cup (diameter 8 cm, height 7 cI11), and inject 2 to 3 wingless viviparous female adult green peach aphids into the cup.
Three animals were inoculated and allowed to give birth. Two days after inoculation, the adults were removed and the number of larvae was counted. The eggplants infested with larvae were treated with soil irrigation treatment with 10 ml of the chemical solution adjusted to the above-mentioned concentration, and left in a thermostat with lighting at 26°C. Five days after the treatment, survival was determined, and the survival rate was determined in the same manner as in Test Example 3 above.

In addition, detached insects were considered to be dead.

Compounds 1.2.4.6.7 and 8 showed 100% mortality.

Disperse each preparation of the active ingredient compound in water for 80 minutes.
Cabbage leaf pieces were immersed in the chemical solution adjusted to a concentration of 0 ppm for about 10 seconds and air-dried. A Petri dish with a diameter of 90 mm was lined with moist filter paper, and the air-dried leaf pieces were placed on top of it. Ten 2nd to 3rd instar Spodoptera larvae were released there, the lid was placed, and the larva was left in a lighted incubator at 26°C. The survival rate was determined in the same manner as in Test Example 1, by determining whether the insects were alive or dead at the 5th millet after becoming adults.

Compounds 1.6 and 8 showed 100% mortality.

Next, formulation examples of the present invention will be described, but the compounds, compounding ratios, dosage forms, etc. of the present invention are not limited to the described examples.

Formulation Example 1 (a) 20 parts by weight of compound t1m4 (b) 72 parts by weight of kaolin (c) 1 part or more of ligninsulfonic acid sorter 8ffii are mixed uniformly to prepare a wettable powder.

Formulation Example 2 (a) Compound 11 is uniformly mixed with 1.15 parts by weight (b) 95 parts by weight or more of talc to form a powder.

Formulation example 3 (a) Compound! Ik12 20 parts by weight (
b) 20 parts by weight of N,N'-dimethylformamide (c) Polyoxyethylene alkylphenyl ether
10 parts by weight (d)xylene
50 parts by weight or more are uniformly mixed and dissolved to form an emulsion.

Formulation Example 4 (a) Kaori 7 68 parts by weight (b) Sodium ligninsulfonate 2 parts by weight (c) Polyoxyethylene alkylaryl sulfate
5 parts by weight (d) Fine powder silica A mixture of 25 parts by weight or more of each component and compound 11h4 in a 4:1 ratio
Mix in weight proportions to form a wettable powder.

Formulation Example 5 (a) Compound No. 8 40 parts by weight (b) Oxylated polyalkylphenol phosphate-triethanolamine 2
Parts by weight (c) Silicone 0.2 parts by weight (d) Xanthan gum o, i parts by weight (e) Ethylene glycol 5 parts by weight (f) Water
52.7m31 parts or more are uniformly mixed and pulverized to make a flowable agent.

Formulation Example 6 (a) Compound 6 50 parts by weight (b) Oxylated polyalkylphenyl phosphate
Triethanolamide 22 parts by weight (c) Silicone 0.2 parts by weight (d)
Add 47.8 parts by weight or more of water to the pulverized stock solution and add (e) 5 parts by weight of sodium polycarboxylate (f) anhydrous sodium sulfate.
Add 42.8 parts by weight, mix uniformly, and dry to obtain a dry flowable agent.

Formulation example 7 (a) Compound level 7 5 parts by weight (b) Polyoxyethylene octylphenyl ether
1 part by weight (c) 0.5 part by weight of polyoxyethylene phosphoric acid ester (d) 93.5 parts by weight of granular calcium carbonate (a)
- (C) were mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed on (D) to remove acetone to obtain granules.

Formulation example 8 (a) Compound fish 8 2.5 parts by weight (b) N
- Methyl-2 to 2.5 parts by weight of pyrrolidone (c) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to form a micro-spraying agent (ultra
(low volume formulation)
shall be.

Formulation example 9 (a) Compound 4 5 parts by weight (b) N
, 15 parts by weight of N-dimethylformamide (c) polyoxyethylene alkylaryl (aryl
)Ether io parts by weight (d)xylene
7o! A certain amount or more of the ingredients are mixed uniformly to form an emulsion.

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^1, R^2 and R^3 each independently represent a hydrogen atom, An alkyl group or an acyl group, provided that R^
1. When either one of R^2 and R^3 is an acyl group, the other two are a hydrogen atom or an alkyl group) or a salt thereof. 2. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^1, R^2 and R^3 are each independently a hydrogen atom, an alkyl group or an acyl group. Yes, but R^
1. When one of R^2 and R^3 is an acyl group, the other two are a hydrogen atom or an alkyl group) or a salt thereof as an active ingredient. A characteristic pest control agent. 3. General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1 and R^2 are each independently a hydrogen atom, an alkyl group, or an acyl group, but, R^1 and R
^2 is not an acyl group at the same time) and general formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III) (In the formula, R^3 is a hydrogen atom, an alkyl group, or an acyl group, However, when either R^1 or R^2 is an acyl group, R^3 is a hydrogen atom or an alkyl group) General formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼...(I) (In the formula, R^1, R^2 and R^3 are as described above) A method for producing a nitroguanidine derivative or a salt thereof. 4. General formula (I-1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼…(I-1) (In the formula, R^4 is an alkyl group or acyl group) A compound represented by the general formula ( IV) R^5-X...(IV) (In the formula, R^5 is an alkyl group or an acyl group, and X is a leaving group, provided that when R^4 is an acyl group, R^5
is not an acyl group) (I-2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...( I-2) (In the formula, R^4 and R ^5 is as described above) A method for producing a nitroguanidine derivative or a salt thereof. 5. General formula (I-1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I-1) (In the formula, R^4 is an alkyl group or acyl group) A compound represented by the general formula ( V) R^6-X...(V) (In the formula, R^6 is an alkyl group and X is a leaving group). 3) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I-3) A method for producing a nitroguanidine derivative or a salt thereof represented by (in the formula, R^4 and R^6 are as described above).