JPH0320201A - Production of highly active agricultural chemical dust - Google Patents

Abstract

PURPOSE:To obtain an agricultural chemical dust having ultrahigh insecticidal effects by predissolving a part or all of a benzoylphenylurea-based insecticidal ingredient which is an active ingredient into an organic solvent when producing the dust. CONSTITUTION:A highly active agricultural chemical dust, obtained by predissolving a part or all of a benzoylphenylurea-based compound which is an active ingredient into an organic solvent (e.g. acetone or N-methyl-2- pyrrolidone) in an insecticidal dust containing the above-mentioned active ingredient, injectingly adding the resultant solution into dust ingredients, such as a carrier and surfactant, homogeneously mixing the ingredients thus capable of exhibiting ultrahigh insecticidal effects. The objective insecticidal agricultural chemical dust capable of exhibiting high activity can be readily and advantageously produced according to the aforementioned method.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a method for producing a highly active agrochemical powder, and more specifically, to a method for producing an agrochemical powder containing a benzoylphenylurea insecticidal component as an active ingredient. .

[Conventional technology]

Traditionally, diflubenzu
ron), Triflumuron
, chlorofluazuron (Chlorf luazur)
on), Teflu-benzu on)
ron), Flufenox
Insecticidal powders containing many penzoyl phenyl urea compounds such as P. uron as active ingredients have been studied. These powders are made by adding a carrier and a surfactant to the active ingredient,
It is manufactured by mixing and pulverizing, and when used, it is directly sprayed onto the target object using a spraying device such as a vibrator.

[Problem to be solved by the invention]

However, Diflubenzuron, Tri
flumuron, Chlorfluazuron,
Teflubenzuron, Flufenoxur
Powder formulations containing on and the like as active ingredients have a drawback of being inferior in activity compared to emulsions, flowable formulations, and wettable powders.

When spraying such a powder onto a target object, in order to expect a high insecticidal effect, it is necessary to spray a large amount, which is undesirable from the viewpoint of environmental problems and cost.

[Means to solve the problem]

The present inventors have conducted various studies on the production of agrochemical powders that do not have such drawbacks. As a result, they found that an extremely high insecticidal effect can be obtained by pre-dissolving part or all of the active ingredient in an organic solvent such as acetone or N-methyl-2-pyrrolidone during powder preparation. .

According to the present invention, therefore, when producing an agrochemical powder containing a penzoyl phenyl urea insecticidal compound as an active ingredient, it is characterized in that part or all of the active compound is dissolved in an organic solvent in advance. A method for producing a highly active pesticide powder is provided.

Organic solvents useful in the present invention include methyl alcohol,
Alcohols such as ethyl alcohol, isopropyl alcohol, and ethylene glycol; ketones such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; ethers such as dioxane and tetrahydrofuran; aldehydes such as furfural; and aliphatic hydrocarbons such as kerosene and kerosene. , xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, aromatic hydrocarbons such as solvent naphtha 1, chloroform,
Halogenated hydrocarbons such as chlorobenzene, carbon tetrachloride, dichloromethane, esters such as glycerin esters of fatty acids, nitriles such as acetonitrile, N-
Mention may be made of strongly polar solvents such as methyl-2-pyrrolidone, dimethylsulfoxide, dimethylformamide, and optionally epoxidized vegetable oils, such as epoxidized soybean oil or coconut oil.

Suitably, acetone, dichloromethane, chloroform,
Easily volatile solvents such as methyl alcohol, N-methyl-2-
A hardly volatile solvent such as pyrrolidone, cyclohexanone, dimethylformamide, acetophenone, or furfural is added to the active compound in a l:o ratio. Add at a ratio of 1 to 1:100.

After part or all of the active ingredient is dissolved in the organic solvent, a carrier (diluent), auxiliary agent, etc. are generally added thereto, and in some cases, a surfactant is also added.

As the surfactant, sulfate and sulfonate type anionic surfactants are mainly used. Also,
A polyoxyethylene type nonionic surfactant, a water-soluble polymer substance, a polyoxyethylene ether type phosphate ester type anionic surfactant, etc. may be used. The sulfate-based anionic surfactant has 12 carbon atoms.
~18 alkyl sulfates (salts include Na, K, NH,
and various salts of amines, etc.), polyoxyethylene alkyl (
C8-12) phenyl ether sulfate (NaNH.
and various salts of amines, etc.), polyoxyethylene alkyl (
Examples include ether sulfates (having 12 to 18 carbon atoms) (salts of NaNH. and amines, etc.), polyoxyethylene polyoxypropylene block polymer sulfates (salts of Na.NH. and amines, etc.). In addition, as a sulfonate-based anionic surfactant, dodecylbenzenesulfone}
(Na .NH4 2itCF amine salt), mono- and dialkyl (4 carbon atoms) naphthalene sulfonate (Na
and NH, salt), naphthalene sulfonate (Na salt) formalin condensate, dialkyl (carbon number 6-8> sulfosuccinate (Na salt) and lignin sulfone} (N
a and Ca salt). In addition to this,
Examples of nonionic surfactants include polyoxyethylene nonylphenyl ether, polyoxyethylene styryl (or pendyl) phenyl ether, polyoxyethylene sorbitan alkylate, polyoxyethylene fatty acid ester having 12 to 18 carbon atoms, and the like. Examples of polymeric substances include PVA, CMC, starch, alginates, polyacrylates (Na and amine salts), etc. In some cases, cationic surfactants and zwitterionic surfactants are used. You can also do that.

Examples of carriers (diluents) include vegetable powders such as soybean flour and wheat flour, mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, clay, kaolin, calcium carbonate, acid clay, montmorillonite, feldspar, and quartz, and benzoin. Organic and inorganic compounds such as acid soda, urea, mirabilite, alumina, and silicic acid (so-called white carbon) are used.

In addition, auxiliary agents other than carriers commonly used in agricultural chemicals, such as spreading agents, preservatives, emulsifiers, decomposition inhibitors, assimilation inhibitors,
If necessary, an activity enhancer such as soybean lecithin may be appropriately added to ensure the insecticidal effect. In addition, if necessary, other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc. may be mixed or used together. In this case, even better effects may be obtained.

For example, insecticides, acaricides, or nematicides include O-(4-bromo-2-chlorophenyl)O-ethyl-S-propylphosphorothioate, 2,2-dichlorovinyldimethylphosphate, ethyl-3- Methyl-
4-(Methylthio)phenylisobrobyl phosphoroamidate, 010-dimethyl 10-4-nitro-m-}lyl phosphorothioate, 01ethyl 10-4-nitrophenylphenylphosphonothioate, ○*O-diethyl 10-2-isopropyl-6-methylpyrimidine-4-
ylphosphorothioate}, O,O-dimethyl10- (
3,5.6-trichloro-2-biridyl) phosphorothioate, ○,S-dimethylacetyl phosphoroamidothioate, ○-(2,4-cyclophenyl)-0-ethyl-S-7'' pyruphosphorodithioate. Organic phosphate ester compounds; 1-naphthylmethyl carbamate, 2-isobropoxyphenylmethyl carbamate, 2-methyl-2-(methylthio)propionaldehyde, ○-methyl Rubamoyloxime, 2,3-dihydro- 2.2-dimethylbenzofuran-7-ylmethylcarbamate, dimethyl-N.N' - (thiobis[
(Methylimino)carbonyloxy〉]bisethanimidothioate, S-methyl-N-(methylcarbamoyloxy)thioacetimide}, N,N-dimethylcarbonyloxyimino-2-(methylthio)acetamide, 2-( Ethylthiomethyl> Carbamate-based compounds such as phenylmethyl carbamate, 2-dimethylamino-5.6-dimethylpyridin-4-yldimethylcarbamate, S-S'-2-dimethylaminotorJ methylenebis(thiocarbamate); 2.2.2-}lichloro-1.1-bis(4-chlorophenyl)ethanol, 4
-chlorophenyl-2・4.5-}! Organochlorine compounds such as J chlorophenylsulfone; organometallic compounds such as tricyclohexyl sulfone hydroxide; (
RS) monoalpha-cyano-3-phenoxypenzylene (RS)
)-2- (4-chlorophenyl>-3-methylbutyrate, 3-phenoxybenzyl-(IRs) monocis, trans-3- (2.2-dichlorovinyl)-2.2-
Dimethylcyclopropane carboxylate, (RS)-α-cyano-3-phenoxybenzyl (IRS)-cis, trans-3-(2,2-dichlorovinyl)-2
, 2-dimethylcyclobrobancarboxylate, (S
)-α-cyano-3-phenoxybenzyl-(I R)
1cis-3-(2.2-dibromovinyl>-2.2-
Dimethylcyclopropanecarboxylate, (RS)-α-cyano-3-phenoxybenzyl (IRS)-cis, trans-3-(2-chloro3.3.3-trifluorobropenyl)-2.2-dimethylcyclobroban carboxylate, 4-methyl-2.3,5.6-tetrafluorobenzyl-3-(2-chloro3.3.3-
pyrethroid compounds such as 2-tert-butylimino-3-isobrobyl-5-phenyl-3,4.5.6-tetrahydro-2H-1. 3.5-Thiadiazin-4-one, trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oisothiazolidinone-3-carboxamide, N-methylbis(2.4-xyl) liminomethyl)amine, N'-(4-chloro-1-tolyl)-N. Compounds such as N-dimethylformamidine; isobrobyl-(2E・4E)-11-methoxy-3
．． Juvenile hormone-like compounds such as 7.11-}limethyl-2,4-dodecadienoate; other compounds include dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, etc. . Furthermore, B
It can also be mixed or used in combination with microbial pesticides such as T agents and insect pathogen virus agents.

For example, the fungicides include S-benzyl-0.0-diisobrobyl phosphorothioate, 〇1ethyl-S,S-
Organophosphorus compounds such as diphenylphosphorodithioate and aluminum ethyl hydrogen phosphonate;
4. Organochlorine compounds such as 5,6.7-tetrachlorophthalide and tetrachloroisophthalonitrile; polymers of Manganese ethylene bis(dithiocarbamate);
Zinc ethylene bis(dithiocarbamate) polymer,
Salt compound of zinc and maneb, didizinc bis(dimethyldithiocarbamate), ethylene bis(dithiocarbamate), zinc propylene bis(dithiocarbamate)
dithiocarbamate compounds such as polymers of 3a.
4,7a-Tetrahydro N-(}lichloromethanesulfenyl)phthalimide, 3a. N-halogenothioalkyl compounds such as 4,7.7a-tetrahydro N-(1.1·2.2-tetrachloroethanesulfenyl)phthalimide, N-(}'Jchloromethylsulfenyl)phthalimide; 3- (3,5-dichlorophenyl)
-N-isobrobyl-2.4-dioxoimidazolidine-1-carboxamide, (RS)-3- (3.5-dichlorophenyl)-5-methyl-5-vinyl-1.3-
Oxazolidine-2,4-dione, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1
．． Dicarboximide compounds such as 2-dicarboximide; methyl-1-(butylcarbamoyl)penzimidazol-2-ylcarbamate, dimethyl-4.4'
- Penzimidazole compounds such as (0-phenylene>bis(3-thioallophanate); 1- (
4-chlorophenoxy>-3,3-dimethyl-1- (
IH-1.2.4-}Riazole-1-yl>Butanone, 1-(biphenyl-4-yloxy)-3.3-dimethyl-1- (IH-1.2.4-}Riazole-1-
yl)butan-2-ol, 1-(N-(4-chloro-2-trifluoromethylphenyl)-2-propoxyacetimidoyl]imidazole, 1-(2-(2,4-
dichlorophenyl)-4-ethyl-1,3-dioisolan-2-ylmethyl)-1H-1.2.4-}riazole, 1-(2-(2.4-dichlorophenyl)-4
-7” Lobi-1.3-dioxolan-2-ylmethyl)-1H-1.2.4-}riazole, 1- (2-(
2.4-dichlorophenyl〉pentyl)-1H-1.2
．． Azole compounds such as 4-triazole; 2.4
'-dichloroα-(pyrimidin-5-yl)benzhydryl alcohol, (±)-2.4'-difluoroα
-(IH-1.2.4-}lyazol-1-ylmethyl> carbinol compounds such as penzhydryl alcohol; 3'-isopropoxy 0-toluanilide, α,
α. α-trifluoro-3′-isopropoxy 0-}
Penzanilide-based compounds such as methyl-N-(2-methoxyacetyl)-N-(2,6-xylyl)-Acylalanine-based compounds such as DL-alaninate; .6-
Dinitro-4-α,α,α-trifluorotolyl)-5
-}trifluorotolyl)-5-trifluoromethyl-2
- Pyridinamine compounds such as pyridinamine; other compounds include piperazine compounds, morpholine compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, urea compounds, antibiotics, etc. .

The insecticidal active ingredient, which is an effective ingredient, is usually contained in the powder at a concentration of 0. 1%
The organic solvent is preferably contained in an amount of 1,710 to 100 times the amount of the effective precept.

The insecticidal powder of the present invention can be easily produced by those skilled in the art using equipment that is readily available. That is, powder components such as carriers and surfactants are put into a ribbon mixer or screw mixer, and heated at room temperature or at 30 to 80°C as necessary.
While mixing under heating conditions of , a part or all of the insecticidal active ingredient dissolved in an organic solvent at room temperature or, if necessary, under heating conditions of 30 to 80° C. is added and mixed. Next, in order to thoroughly and uniformly mix the active ingredient or surfactant, the 1 ump is crushed through a crusher such as a hammer mill, pin mill, or jet otomizer. Furthermore, if this is uniformly mixed again using a ribbon type mixer or a screw type mixer, the desired insecticidal powder can be obtained. Furthermore, if a high-speed rotary blade type mixer such as a juice mixer type mixer or a Henschel mixer is used, each of the above-mentioned mixing, pulverizing, and mixing steps can be performed using the same device by adjusting only the stirring speed. .

〔Example〕

Next, Examples, Comparative Examples, and Test Examples of the insecticidal powder of the present invention will be shown. It goes without saying that the types and blending ratios of additives are not limited to these, and can be varied within a wide range.

Note that parts and % are parts by weight and % by weight, respectively.

Example 1 1-(3.5-dichloro-4-(3-chloro-5-trifluoromethyl-2-biridyloxy)-7enyl)-
3-(2,6-difluorobenzoyl)urea 0.
3 parts of N-methyl-2-pyrrolidone was dissolved in 2 parts of N-methyl-2-pyrrolidone at room temperature, and 2 parts of white carbon, 3 parts of calcium stearate and 92.7 parts of clay were mixed therein, ground, and powdered according to a conventional method. Obtained.

Example 2 1-[3.5-dichloro-4-(3-chloro-5-trifluoromethyl-2-biridyloxy)-phenyl)-
3-(2,6-difluorobenzoyl)urea 0.3
1 part was dissolved in 30 times the volume of methyl alcohol, 5 parts of white carbon was added thereto, 30 parts of talc and 64.7 parts of clay were added thereto, and after volatilizing the methyl alcohol with a rotary evaporator, they were mixed uniformly. death,
It was crushed to obtain a powder according to a conventional method.

Example 3 0.3 part of 1-(3.5-dichloro-2.4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea was added to 50 times the amount of chloroform under heating conditions of 40°C. 4 parts of white carbon, 1 part of Drillless A, and 15 parts of clay were added to this, and after the chloroform was evaporated in a rotary evaporator, 7967 parts of DL clay was added, mixed uniformly, pulverized, and constantly heated. DL powder was obtained according to the method.

Example 4 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl>urea 0
．． Dissolve 3 parts in 3 parts of furfural, add 3 parts of white carbon, 1 part of Drilless A, 10 parts of clay and D
Add 82.7 parts of L clay, mix uniformly, crush,
A DL powder was obtained according to a conventional method.

Example 5 1-(3,5-dichloro-4-(1,1.2.2-
tetrafluorophenyl)-3-(2.'
6-difluorobenzoyl〉urea (0.2 parts) was dissolved in 2.5 parts of acetophenone, and white carbon 4
Department, Doriles AO. Part 5, PAPO. 5 parts of DL clay and 92.3 parts of DL clay were mixed and ground to obtain a DL powder according to a conventional method.

Example 6 1-(3,5-dichloro-4-(1.1・2・2-
tetrafluoroethoxy>-phenyl]-3-(2.6
-Difluorobenzoyl>urea 0. 2 parts were dissolved in 3 parts of cyclohesanone heated to 40°C, and 5 parts of white carbon, 2 parts of calcium stearate, and 89.8 parts of clay were uniformly mixed therein and ground to obtain a powder according to a conventional method. .

Example 7 1-C3.5-dichloro-4- {1,1.2・2-
Tetrafluoroethoxy}-phenyl]-3-(2.6
-difluorobenzoyl)urea 0. Dissolve 2 parts in 100 times the volume of acetone, add 5 parts of white carbon, then add 20 parts of clay, volatilize the acetone with a rotary evaporator, and then dissolve 74 parts of clay.
．． 8 parts were added, mixed uniformly, and ground to obtain a powder according to a conventional method.

Example 8 1-(3.5-dichloro-4-(1.1,2.2-
Tetrafluoroethoxy)monophenyl)-3-(2.6
-difluorobenzoyl)urea 0. 2 parts of N-methyl-2-pyrrolidone was dissolved in 1.8 parts of N-methyl-2-pyrrolidone, and 2.5 parts of white carbon, 0.5 parts of Drilleth A, and 1 part of clay were dissolved in 1.8 parts of N-methyl-2-pyrrolidone.
0 parts and 85 parts of DL clay were added, mixed uniformly, and ground to obtain a DL powder according to a conventional method.

Example 9 0.4 part of 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea was partially dissolved in 5 times the amount of dichloromethane, and 2 parts of white carbon, 20 parts of talc and clay were added to the solution. After adding 77.6 parts of the mixture and volatilizing dichloromethane using a rotary evaporator, the mixture was mixed uniformly and pulverized to obtain a powder according to a conventional method.

Example 10 1- (4-}lifluoromethoxy) -3- (2-
0.4 part of chlorobenzoyl>urea was partially dissolved in 1 part of N-methyl-2-pyrrolidone under heating conditions of 40°C, and 1 part of white carbon and 0.5 parts of Drilleth A were dissolved in this solution.
Department, P A P 0. 5 parts and DL Cre, -96.
Add 6 parts of D
L powder was obtained.

Example 11 1-(2-fluoro-4-(2-chloro4-(2-chloro4-trifluoromethylphenoxy>-phenyl)-3-(2,6-difluorobenzoyl>urea 0
．． 4 parts were dissolved in 6 parts of acetophenone, 5 parts of white carbon, 87.6 parts of DL clay were added, and the mixture was mixed uniformly and pulverized to obtain a DL powder according to a conventional method.

Comparative Example 1 A powder was obtained in the same manner as in Example 1 except that N-methyl-2-pyrrolidone was not used and 94.7 parts of clay was used instead.

Comparative Example 2 A powder was obtained in the same manner as in Example 2 without using methyl alcohol.

Comparative Example 3 A powder was obtained in the same manner as in Example 3, but without using chloroform.

Comparative Example 4 D was prepared in the same manner as in Example 4, but without using furfural and using 85.7 parts of DL clay instead.
L powder was obtained.

Comparative Example 5 In the set of Example 5, acetophenone was not used,
A DL powder was obtained in the same manner using 94.8 parts of DL clay instead.

Comparative Example 6 A powder was obtained in the same manner as in Example 60 except that cyclohexanone was not used and 92.8 parts of clay was used instead.

Comparative Example 7 A powder was obtained in the same manner as in Example 70 without using acetone.

Comparative Example 8 A DL powder was obtained in the same manner as in Example 8 except that N-methyl-2-pyrrolidone was not used and 86.8 parts of DL clay was used instead.

Comparative Example 9 A powder was obtained in the same manner as in Example 90 without using dichloromethane.

Comparative Example 10 A DL powder was obtained in the same manner as in Example 10 except that N-methyl-2-pyrrolidone was not used and 97.6 parts of DL clay was used instead.

Comparative Example 11 A DL powder was obtained in the same manner as in Example 11 except that acetophenone was not used and 93.7 parts of DL clay was used instead.

Test Example 1 Effect example 1.2 on rice beetle
．． The powders of Comparative Examples 1.3 and 4 and Comparative Examples 1.2, 3 and 4 were applied to rice plants planted in pots inoculated with third instar larvae of the rice beetle using a bell jar duster. The treated pots were placed in cages and stored in a constant temperature and humidity room at a temperature of 25° C. and a humidity of 80%, and the insecticidal rate was examined after 5 days. The test is 1 pot 10
Each head was inoculated and the treatment was carried out in two pots.

The test results are shown in Table-1.

Table 1: After washing, the 3rd instar larvae of the kobuno borer were released into a cup, and the temperature was 25°C.
It was stored in a constant temperature room at 65% humidity and the insect killing rate was examined after 6 days. The test was conducted with 1 cutlet of 75 cows and a 4 cup liter treatment.

The test results are shown in Table-2.

Table 2 Test Example 2 Effect on the Kibno borer moth The powders of Examples 5.6.7 and 8 and Comparative Examples 5, 6.7 and 8 were sprinkled on rice seedlings placed in PVC cups using a bell jar duster. Failure test example 3 Effect example 9 on Nikamaichi Chiuu. The powders of IO and 11 and Comparative Examples 9, 10 and 11 were applied to budding rice seedlings placed in PVC cups using a bell jar duster. After spraying, 10-day-old larvae of P. elegans were released into a cup and stored in a constant temperature and humidity room at a temperature of 25° C. and a humidity of 80%, and the insecticidal rate was examined after 5 days. The test was conducted with 5 animals per cup and 4 cups per treatment.

The test results are shown in Table-3.

DIT Margin Table-3 [Effects of the Invention] According to the method of the present invention, it is possible to easily produce an insecticidal agricultural powder that exhibits high activity.

Claims (1)

[Claims] 1. When producing a pesticide powder containing a benzoylphenylurea insecticidal component as an active ingredient, a highly active pesticide powder is used, which is characterized in that part or all of the active ingredient is dissolved in an organic solvent in advance. Manufacturing method.