JPH02275806A - Insecticidal emulsifiable concentrate or wettable power - Google Patents

Abstract

PURPOSE:To obtain the subject agent having extremely high stability, low toxicity and high insecticidal effect and applicable without troubles by adding a water-miscible solvent and an allylalkane compound having >=2 phenyl groups to bensultap and converting the mixture into emulsifiable concentrate or wettable powder. CONSTITUTION:An agricultural insecticide having excellent emulsion stability and insecticidal effect can be produced by adding an allylalkane compound having >=2 phenyl groups (e.g. phenylxylylethane) and a water-miscible solvent to bensultap [1,3-bis(benzenesulfonylthio)-2-(N,N-dimethylaminoipropane]. The amounts of the allylalkane compound and the water-miscible solvent are preferably 0.05 to 1 pts.wt. and 0.1 to 5 pts.wt. per 1 pt.wt. of bensultap, respectively. The precipitation of bensultap crystal in the emulsifiable concentrate or wettable powder does not take place during the storage or the preparation of spraying liquid. Furthermore, the agent does not clog the spray-nozzle of a sprayer and exhibits excellent insecticidal effect.

Description

DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to an agricultural insecticidal formulation that is emulsion stable and has excellent insecticidal efficacy.

"Prior art" 1.3-bis(benzenesulfonylthio)-2-(N,
N-'; methylamino)propane (bensultap) is a compound with excellent insecticidal activity (Japanese Patent Publication No. 46-1989).
13755) is difficult to prepare by conventional means. That is, it has poor solubility in solvents commonly used for emulsions, such as xylene (5° C., 5 g/100 Wj2 or less), and practical emulsions of bensultap cannot be prepared using these solvents. In addition, N-methylpyrrolidone (hereinafter abbreviated as NMP), dimethylformamide (hereinafter abbreviated as DMF), etc. dissolve bensultap well (5°C, 100g/100- or more), but in addition to these solvents, various surfactant Even if a bensultap emulsion is prepared using a bensultap emulsion, if it is diluted with water to prepare a spray solution, these solvents are miscible with water in any proportion, so bensultap easily precipitates in water without emulsifying. As a result, troubles such as the nozzle nozzle of the sprayer being blocked occur, causing uneven spraying and reducing the pest control effect.As a result, Bensultap's emulsion and wettable powder were not commercialized. There wasn't.

``Problem to be solved by the invention'' Bensultap is an excellent insecticidal ingredient with low toxicity to fish.
If it is made into an emulsion or an irrigation agent using conventional methods, Bensultap will precipitate without being emulsified during preparation of the spray solution, making it impossible to achieve the desired insecticidal effect. Therefore, the development of a practical bensultap emulsion or wettable powder has been awaited.

"Means for Solving the Problems" The inventors of the present invention found that when Bensultap, which originally has an excellent pest control effect, is made into a conventional emulsion using xylene, etc., which is commonly used as a solvent, it is possible to spray Sometimes Bensurutap precipitates and blocks the nozzle of the sprayer, making it impossible to spray, causing uneven spraying, and even blocking absorption and contact with pests, making it impossible to obtain sufficient pest control effects. After intensive research to overcome the drawbacks of the above, we produced emulsions and wettable powders containing bensultap, a water-miscible solvent, and allyl alkanes having two or more phenyl groups, and unexpectedly found that they were stable. It has been discovered that a preparation can be obtained which has ideal properties such as being extremely effective, causing no trouble in spraying, having low toxicity, and having an extremely good insecticidal effect, and based on this finding, the present invention has been completed.

That is, the present invention provides (1) (i) bensultap, (n)
Allyl alkanes having two or more phenyl groups and (i
i) Insecticidal emulsion or irrigation agent containing a water-miscible solvent; (2) (i) for 1 part by weight of Pensultag; (■);
0.0 allyl alkanes having two or more phenyl groups
the insecticidal emulsion or irrigation agent according to item (1), containing 5 to 1 part by weight and (i) 0.1 to 5 parts by weight of a water-miscible solvent; (3) allylalkanes having two or more phenyl groups; is phenylxylylethane (hereinafter abbreviated as PXE), bis-
(α-methylbenzyl)xylene (hereinafter abbreviated as BMBX), l-xylyl-1-[(α-methylpencyl)phenyl]ethane (hereinafter XMB P E, !: abbreviated) and l-xylyl-1,3-diphenyl Butane (hereinafter XD
The present invention relates to the insecticidal emulsion or wettable powder according to item (1) or item (2), which is one or more selected from the following.

In the insecticidal emulsion or aquarium of the present invention, pensultag is used as an insecticidal component. Bensultap is used in an amount of 5 to 90% by weight, preferably 10 to 3% by weight based on the entire formulation.
The content is preferably 5% by weight.

The allyl alkanes having two or more phenyl groups have a molecular weight of 100 to 1,500, preferably 150 to 600. Allyl alkanes used in the present invention are sparingly soluble in water (0,001 to 0.5 g/100 - preferably 0.01 to 0.05 g/100 su), and benzultap is sparingly soluble in water (5 g/100+42 below)
Therefore, it cannot be used as a water-miscible solvent. Such allyl alkanes include, for example, PXE (for example, ■Tsurpol 7065, manufactured by Toho Chemical Industry Co., Ltd.), BM
BX, XMBPE, XDPB, etc. are used, and these are 1
It is used either as a species or as a mixture of two or more species in an appropriate ratio.

In the present invention, it is preferable to use such allylalkanes as a mixture, and specific examples of mixtures include a mixture of PXE and XMBPE, a mixture of BMBX and XMBP
■Mixtures of E and xDPB (for example, Tsurupol 7355, manufactured by Toho Chemical Industries, Ltd.), mixtures of PXE, BMBX, and XDPB, P
A mixture of XE, BMBX, xMBP'E, and XDP'B (for example, Tsurupol 7537, manufactured by Toho Chemical Industry Co., Ltd.) is used. The allylalkane having two or more phenyl groups in the present invention is preferably 0.05 to 1 part by weight per 1 part by weight of bensultap.
．． 4 to 0.6 parts by weight are used.

In addition, as a water-miscible solvent, 5g/bensultap is used.
Those that can dissolve at least 100 u2 (5°C) and at least 20 d/100 m (20°C) in water are used, such as ketones such as acetone (hereinafter abbreviated as AC), methyl ethyl ketone, and dimethylformamide (hereinafter referred to as AC). DMF), acid amides such as dimethylacetamide, nitriles such as acetonitrile (hereinafter referred to as AN), propionitrile, N-methylpyrrolidone (hereinafter referred to as NMP), etc., as appropriate. Mix and use. Preferred such water-miscible solvents are, for example, AC, DMF, ANINMP or mixtures thereof. The amount of water-miscible solvent used is 0.1 to 5 parts by weight per 1 part by weight of bensultap,
Preferably it is 0.5 to 2 parts by weight.

The insecticidal emulsion or wettable powder of the present invention comprises Pensultag,
It can be obtained by containing an allylalkane having two or more phenyl groups and a water-miscible solvent to form an emulsion or a wettable powder. If necessary, solid carriers, emulsifying agents, suspending agents, spreading agents, penetrating agents, wetting agents, mucilage agents, stabilizers, etc. may be added to the preparations of the present invention, and emulsifying agents can be prepared by methods known per se. Or it can be prepared into a wettable powder.

Solid carriers (diluents and bulking agents) include animal and plant powders (for example, soybean flour, tobacco flour, wheat flour, wood flour, etc.), mineral powders (for example, kaolin, bentonite).

Clays such as acid clay, talcs such as talcum powder and waxite powder, silicas such as diatomaceous earth and mica powder, etc.), alumina, sulfur powder, activated carbon, etc. are used, and one or more of these are mixed in an appropriate manner. They can be mixed and used as appropriate.

As surfactants used as emulsifiers, spreaders, penetrating agents, dispersants, etc., soaps, polyoxyethylene alkylaryl nitrates [e.g., Neugen, E.N. 142 (E・A142) ・Manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
Manufactured by Toho Chemical Co., Ltd., -11 Calgen ■ST-10° [F
] New Calgen 5T-50: manufactured by Monomoto Yushi Co., Ltd.].

Alkyl sulfates [e.g. Emar 10e, Emar 40
■: manufactured by Kao Corporation], alkyl sulfonates [eg, Neogen color Neogen T ■: manufactured by Dai-Kogyo Seiyaku Co., Ltd., Neoperex ■: manufactured by Kao Corporation].

Polyethylene glycol ethers [e.g. Noniball 8
5O, Nonipol 100■, Nonipol 1600: manufactured by Sanyo Chemical Co., Ltd.], polyhydric alcohol air care,! [Example 1.
Wee 2o■9. Weare [F] 80: Nonionic and anionic surfactants such as 1 manufactured by Kao Corporation are used.

In addition, the formulation of the present invention may contain, for example, other types of insecticides (pyrethrin insecticides, organophosphorus insecticides, carbamate insecticides, natural insecticides, etc.), acaricides, nematicides, herbicides, and plant hormones. agents, plant growth regulators, fungicides (e.g. copper fungicides, organochlorine fungicides, organic sulfur fungicides, phenolic fungicides, etc.), synergists, attractants, repellents, pigments, fertilizers, etc. It is also possible to mix and use them by appropriately blending them.

The insecticidal emulsion or wettable powder of the present invention thus obtained is
It has extremely low toxicity, is safe, and has excellent insecticidal effects. Therefore, the insecticidal emulsion or hydrating agent of the present invention is effective in controlling sanitary pests, parasitic insects on animals and plants, and mites, and
Dilute with water, increase volume (e.g. 100-100.00)
0x) and spray directly onto plants and animals infested with pests, etc.
It exhibits a strong insecticidal effect when it comes into direct contact with insects, but it also has a strong insecticidal effect when the insect absorbs the insecticide through its roots, leaves, stems, etc. Shows insecticidal action.

Such properties are advantageous for controlling sweat-absorbing and biting insects or mites. The insecticidal emulsion or irrigation agent of the present invention has both safe and advantageous properties as an agricultural pest control agent, such as less phytotoxicity to plants and less toxicity to fish when used in accordance with conventional methods.

Specifically, the insecticidal emulsion or water conservancy of the present invention can be applied to, for example, Eurydema rugosum,
Scolinophara 1u
rida), Riptortus stink bug (Riptortus
clavatus), Nasigunbai (SLephan)
itis nashi), Laodhopper (Laod.
elphax 5triatellus), brown planthopper (Nilaparvata lugens),
Nephotettix cin
cticeps), Iinasp
is yanonensis), soybean aphid (
Aphis glycines), radish aphid (Lipaphis erysimi), radish aphid (Brevicoryne bras)
sicae), cotton aphid (Aphis gos
sypii), white-legged planthopper (Sogattelafu)
rcifera), southern stink bug (Nezara
viridula), whitefly (Trial
eurodes vaporor iorum), green peach aphid (Myzuspers 1cae), and pseudococcus combus (Pseudococcus comis).
tocki), apple aphid (Aphis pr
omi), green stink bug (Nezara spp,)
, Bedbug (Cimex IecLularius)
), Hemiptera pests such as Psylla spp., Spodoptera spp.
1itura), diamondback moth (Plutellaxyl)
ostella), cabbage butterfly (Pieris)
rapaecruc 1vora), Nikamay moth (Ch.
ilo 5uppressalis), Plusia nigrisigna, Halicovarpa assulta,
Armyworm (Leucania 5eparata)
, Armyworm (Mamestrabrass 1cae)
, Adoxophyesorana
), Notarcha daroga
ta), Cnaphalocrocis
medinalis), potato moth (Phtho
Lepidopteran pests such as Rimaea operculella, e.g.
achna vigintioctopunctat
a), Aulacophora fem
oralis), phyllophore (PhylloLr)
eLa 5triota), rice beetle (eLa 5triota),
Oulema oryzae), rice weevil (Ec
Coleopteran pests such as h inocnemus squameus, e.g.
ica), Culex pipiens (Cu 1expipiens)
pallens), Usiabu (Tabanustri)
gonus), onion haz (Hylemyia a
ntiqua), seed fly (Hylemyia pl)
Diptera pests such as locust locusts (Locusta migratoria) and mole crickets (Locusta migratoria).
Orthoptera pests such as Gryllotalpa africana, such as the German cockroach (Blattel
la germanica), black cockroach (Per
Cockroach pests such as Iplaneta fuliginosa, e.g. Tetranych
usurticae), citrus spider mite (Panonycae)
hus citri), Kanzawa spider mite (Tetra)
nychus kanzawai), black-necked spider mite (Tetranychus cinnabarinu)
s), applefin = (Panenychus ulm)
i), Aculops pelek
spider mites such as Aphelenchoides bessey
It is particularly effective in controlling nematodes such as i).

The insecticidal emulsion or hydrating agent of the present invention can be used in the same manner as conventional insecticidal emulsions or irrigation agents, for example, by spraying on the foliage of crops, spraying insect bodies, etc. against target pests. be able to. The application amount can vary widely depending on the application time, application location, application method, etc., but in general, the final concentration of the active ingredient (insecticidal ingredient) per hectare is 0.1"l100
It may be used after being diluted with water or the like so that Opp is preferably in the range of 10 to 500 pprQ.

"Effect" The insecticidal emulsion or water conservancy of the present invention is extremely safe and exhibits excellent insecticidal action without crystal precipitation of Bensultap during storage or use and no clogging of the nozzle orifice during spraying. This will be clarified in the following test example.

Test Example 1 (Crystal precipitation test and scattering test) The emulsions and wettable powders obtained in Examples 1 to 7 and Control Examples 1 to 3 below were diluted with 3° hard water to a concentration of 500 ppm as Pensultag.
2. Store in a 30℃ incubator,
and the presence or absence of crystal precipitation after 6 hours, and the spraying immediately after preparation (
l Okg/cm sipping nozzle spout (length 30cm
+, caliber 0, 7 mm) The presence or absence of occlusion was examined. The results are shown in Table-1.

(Hereafter, Company, White) Table-1 From this table-■, in emulsions and irrigation agents that do not contain allyl alkanes having two or more phenyl groups, the active ingredient bensultap precipitates from the time of preparing the spray solution, causing problems in spraying. In contrast, the insecticidal emulsion or irrigation agent of the present invention does not precipitate bensultap crystals even after 6 hours have passed after preparing the spray solution, and is found to have extremely good stability without causing any trouble in spraying during preparation.

Test Example 2 (Insecticidal Efficacy Test) Efficacy against the ingested larvae of the Japanese stink bug (materials and methods): Potted rice (Chusei Shinsenbon, 1/10,000 are pot) 45 days after transplantation was inoculated with egg masses of the Japanese stingray moth just before hatching. Three days after inoculation, while rotating the test potted rice in a Susley chamber, spray 30 d/pot of a chemical solution diluted to a predetermined concentration (concentration of Bensultap 250,312,500 ppm) with a spray gun (spraying aE 1 kg/c). (tap water was used for dilution, and a spreading agent Gain manufactured by Ota Pharmaceutical Co., Ltd. was added). Two test sections were established. In addition, egg mass inoculation was carried out in the same manner using Bot rice (same as above) 32 days after transplantation, and 5 test plots were established in which the drug was sprayed in the same manner 2 days after inoculation. In the case of the former, the number of surviving insects was investigated by disassembling the stems 14 days after spraying (effective, and in the latter case, 13 days vk (effective 1F) of spraying), and counting the number of eggshells after the hatched larvae escaped from the inoculated egg mass. The survival rate was calculated using the following formula for the number of sample larvae.The results are shown in Table 2.
(Efficacy I) and Table 3 (Efficacy II).

Table 2: Efficacy against the feeding larvae of the Japanese snail beetle ■From Tables 2 and 3, emulsions and irrigation agents that do not contain allyl alkanes having two or more phenyl groups have poor insecticidal effects and are satisfactory as insecticides. However, it can be seen that the insecticidal emulsion and aquarium of the present invention have extremely excellent insecticidal effects and are satisfactory insecticides.

"Examples" Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.

In the following examples, "parts" means "parts by weight."

Example 1 27 parts of Bensultap, Unicalgen 5T-5015
15 parts of Tsurupol 7065 and 43 parts of NMP were placed in a dissolution tank and stirred to uniformly dissolve them to obtain an emulsion.

Example 2 Bensultap 26.5 parts, Unicalgen 5T-10
12.5 parts, Tsurupol 735513.5 parts, DMF4
7.5 parts of the solution was placed in a dissolution tank and stirred to uniformly dissolve the solution to obtain an emulsion.

Example 3 Bensultap 27.5 parts, Nucalgen 5T-50
15 copies, Tsurupol 7537 15 copies.

42.5 parts of NMP was charged into a dissolution tank and stirred to uniformly dissolve it to obtain an emulsion.

Example 4 Pensultat 7'30.5 parts, Uni-Calgen 5T-5
012, 5 parts, Tsurupol 753,715 parts, NMP25
1 part and 7 parts of AN1 were charged into a dissolution tank, and stirred to uniformly dissolve the mixture to obtain an emulsion.

Example 5 Pensultat 7'27.5L New Calken 5T-10
15 copies, PXEl 0 copies, BMBX 3 copies.

1 part of XDPB, 30 parts of DMF, and 3.5 parts of ANl were placed in a dissolution tank, and stirred to uniformly dissolve the mixture to obtain an emulsion.

Example 6 15 parts of Pensultag, 5 parts of Nucalgen 5T-50, 5 parts of PXE, 3 parts of XMBPE, 10 parts of NMP, 10 parts of diatomaceous earth, 25 parts of white carbon, and 27 parts of clay were added, mixed well, and crushed uniformly using a hammer type crusher. A hydrating agent was obtained.

Example 7 Pensultatsu 7' IO part, Unicalgen 5T-105
, 5 parts, Tsurupol 7537 5 parts, NMP 7.5 parts,
7.5 parts of diatomaceous earth, 30 parts of white carbon, 34 parts of clay
．． 5 parts were added, mixed well with a drum blender, and crushed with a hammer-type crusher to obtain a uniform irrigation agent.

Example 8 25 parts of Pensultag, Unicalgen 5T-5015
15 parts of Tsurpol 7537 and 25 parts of dimethyl sulfoxide were placed in a dissolving tank and stirred to uniformly dissolve them to obtain an emulsion.

Example 9 Bensultap 25 parts, 2 nical) l 7 S T
-5015 copies, Tsurupol 7537 15 copies, AN25
1 part and 20 parts of NMP were charged into a dissolution tank and stirred to uniformly dissolve the mixture to obtain an emulsion.

Example 1O 10 parts of Bensultap, Unicalgen 5T-105,
5 parts, PXE10 parts, NMP 7.5 parts and diatomaceous earth 7.
5 parts, white carbon 30 parts.

29.5 parts of clay was added, mixed well with a drum blender, and crushed with a hammer-type crusher to obtain a uniform wettable powder.

Example 11 25 parts of Bensultap, Nucalgen 5T-5015
1, 20 parts of PXE, and 40 parts of NMP were placed in a dissolution tank and stirred to uniformly dissolve them to obtain an emulsion.

Examples of control formulations that do not belong to the present invention are shown below.

Control example 1 27 parts of Bensultap, Unicalgen 5T-5015
and 58 parts of xylene were charged into a dissolution tank and stirred.
Since it did not dissolve uniformly, it was heated to obtain an emulsion.

Control example 2 Benzultat 7'27.5 parts, Nucalgen 5T-5
015 parts of DMF and 57.5 parts of DMF were charged into a dissolution tank and stirred to uniformly dissolve them to obtain an emulsion.

Control example 3 10 parts of Benslutag, Nucalgen 5T-105,
5 parts, xylene 7.5 parts, diatomaceous earth 7.5 parts.

30 parts of white carbon and 39.5 parts of clay were added and mixed well with a drum blender, and crushed with a hammer-type crusher to obtain a uniform irrigation agent.

"Effects of the Invention" The Bensultap formulations (emulsions and wettable powders) of the present invention do not cause crystals of Bensultap to precipitate during storage or preparation of the spray solution, and do not clog the nozzle orifice of the sprayer during spraying. Since it exhibits an excellent pesticidal effect, it is possible to provide a useful new agricultural chemical formulation.

Agent Patent Attorney Iwa 1) Hiroshi (4 others)

Claims (3)

[Claims] (1) (i) 1,3-bis(benzenesulfonylthio)
-2-(N,N-dimethylamino)propane, (ii)
An insecticidal emulsion or wettable powder containing an allylalkane having two or more phenyl groups and (iii) a water-miscible solvent. (2) (i) 1,3-bis(benzenesulfonylthio)
For 1 part by weight of -2-(N,N-dimethylamino)propane, (ii) 0.05 to 1 part by weight of an allyl alkane having two or more phenyl groups and (iii) 0.05 to 1 part by weight of a water-miscible solvent. The insecticidal emulsion or wettable powder according to claim 1, containing 1 to 5 parts by weight. (3) Allylalkanes having two or more phenyl groups include phenylxylylethane, bis-(α-methylbenzyl)xylene, 1-xylyl-1-[(α-methylpencyl)phenyl]ethane, and 1-xylyl-1-[(α-methylpencyl)phenyl]ethane. Claim (1) is one or more selected from 1,3-diphenylbutane.
) or the insecticidal emulsion or hydrating agent described in (2).