JPH1149617A - Bactericidal, fungicidal and insecticidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition which shows precise controlling effect against various bacteria, fungi and insect pests in low dosages and is high in safety by formulating an iodic compound having bactericidal and fungicidal activities with a specific structure of compound. SOLUTION: This composition is obtained by formulating (A) an iodic compound (e.g. diiodomethyl-p-tolylsulfone, 3-iodo-2-propionyl N-n-butylcarbamate, etc.), having bactericidal and fungicidal activities with (B) a compound of the formula (R1 is H and methyl; R2 -R4 are each H and an 1-3C alkyl). On the mixing ratio in the above-stated components, it is preferable that the component B is mixed in an amount of 0.002-10 pts.wt. based on 1 pts.wt. of the component A. Further, the components A and B are respectively formulated in amounts of 0.000001-95 wt.% in the above-stated composition. In order to administrate this composition, it is preferable to use the active ingredient in a concentration of 0.001-5000 ppm.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel fungicidal and insecticidal composition exhibiting excellent fungicidal and insecticidal activity.
INDUSTRIAL APPLICABILITY The composition of the present invention is useful for disinfecting and killing various industrial raw materials and industrial products, and is also useful for disinfecting and killing insecticides for improving environmental hygiene.

[0002]

2. Description of the Related Art Conventionally, various fungicides and insecticides have been added to various industrial raw materials or industrial products such as paints, pastes, wood, leather, fibers, plastics, and pulp. It is widely practiced to impart a fungicidal and fungicidal effect and an insecticidal effect to raw materials or products. Also,
With the recent increase in hygiene awareness, fungicides and insecticides are widely used for controlling unpleasant pests.

[0003] These industrial raw materials or industrial products are:
Since there are many opportunities for direct contact with the human body, the above-mentioned additives not only have high fungicidal and fungicidal effects and insecticidal effects, but also have high safety for humans and animals, and do not cause problems such as pollution. It is required to be a compound.

In general, it is known that iodine-based fungicides have high safety and a broad antibacterial spectrum.
For example, diiodomethyl-p-tolylsulfone (hereinafter referred to as D
Abbreviated as MTS. ), 3-iodo-2-propynyl Nn-butylcarbamate (hereinafter abbreviated as IPBC), 2,3,3-triiodoallyl alcohol (hereinafter abbreviated as TIAA).
And 3-bromo-2,3-diiodo-2-propenyl carbonate (hereinafter abbreviated as BDPC) are particularly safe for humans and animals and are known as fungicides and algicides. Is a compound of These acute toxicities are oral,
It is extremely low in both dermal and non-dermal properties, and it does not cause skin irritation to humans and does not confer mutagenicity. In addition, discoloration bacteria,
With respect to rot fungi, mold, etc., the effect of suppressing their growth is very excellent.

Although these iodine-based compounds have an insecticidal effect on mites and the like, their effects are only very weak. Therefore, when these iodine compounds are used as fungicidal and fungicidal agents having an insecticidal effect, they must be mixed with other compounds having a high insecticidal effect. As the insecticides, mainly organophosphorus compounds and pyrethroid compounds are known, but these have strong insecticidal activity, but are highly toxic to humans and animals, and can cause rash on the skin and mucous membranes. Therefore, even if these are mixed with, for example, DMTS to produce a fungicide and fungicide, such a composition is not suitable for use in various industrial raw materials or industrial products.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a fungicidal and fungicidal composition which does not have the above-mentioned disadvantages when a compound having a high insecticidal effect is used in combination with an iodine-based fungicide. It is to provide. That is, harmful fungi and pests for the purpose of controlling a wide variety of fungi and pests that cause contamination and deterioration of various industrial raw materials or industrial products, or for the purpose of controlling unpleasant pests to improve environmental health. It is another object of the present invention to provide a fungicidal and fungicidal composition that can be controlled at a low dose and at the same time and that is highly safe.

[0007]

Means for Solving the Problems In order to achieve the above objects, the present inventors have intensively searched for a compound having high safety and excellent insecticidal effect. As a result, with respect to an iodine compound having a fungicidal and fungicidal activity, the compound represented by the general formula (1)

[0008]

Embedded image (Wherein, R ₁ represents a hydrogen atom or a methyl group, R _2, R
₃ and R ₄ represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. When at least one compound represented by the formula (1) is used as a mixture, the composition does not hinder the fungicidal and fungicidal activity of the iodine compound contained therein, and has a very low dose and a broad insecticidal spectrum. Found to be granted. Furthermore, they have found that they exhibit a higher activity than the case of using each alone due to a synergistic effect, and have completed the present invention.

That is, the present invention provides:
[Formula 3]

Embedded image (Wherein, R ₁ represents a hydrogen atom or a methyl group, R _2, R
₃ and R ₄ represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ) And a fungicidal and insecticidal composition comprising a fungicidal and fungicidally active compound, and (2) an iodine-based compound having a fungicidal and fungicidal activity is diiodomethyl-p -Tolylsulfone (DMT
S), 3-iodo-2-propynyl Nn-butylcarbamate (IPBC), 2,3,3-triiodoallyl alcohol (TIAA) and 3-bromo-2,3-diiodo-2-propenylcarbonate (BDPC) The fungicidal and fungicidal composition according to the above (1), which is selected from the group consisting of:

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
In the present invention, the compound represented by the general formula (1)

Embedded image (Wherein, R ₁ represents a hydrogen atom or a methyl group, R _2, R
₃ and R ₄ represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Is a compound having an insecticidal activity against various sanitary pests such as termites, mites, flies and cockroaches, but its toxicity is extremely small and acute toxicity LD
₅₀ is more than 4000mg / Kg orally (rat), 2000m dermal
It is g / Kg or more (rat), has no skin irritation and no mutagenicity, and is extremely safe for humans and animals.
In addition, there is no long-term residual contamination in soil, water, etc., and no harmful substances are generated in the decomposition products. The production method of this compound is described, for example, in JP-A-8-24.
No. 5322.

The mixing ratio of the active ingredient in the fungicidal and insecticidal composition of the present invention is generally the following formula (1) per part by weight of the iodine compound having fungicidal activity.

Embedded image (Wherein, R ₁ represents a hydrogen atom or a methyl group, R _2, R
₃ and R ₄ represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. The compound represented by the formula (1) is 0.002 to 10 parts by weight, preferably 0.05 to 5 parts by weight. In this case, even if the amount is outside the range of 0.002 to 10 parts by weight, the fungicidal and fungicidal effects can be seen, but their synergistic effect is generally small.

The fungicidal composition according to the present invention exhibits an excellent fungicidal and insecticidal effect and exhibits an accurate control effect. Such pests exhibit an extremely broad insecticidal spectrum, for example, armyworm, rice armyworm, phlebotocoyga, tamanayaga, cottontail kiriba, giant tobacco,
White-spotted armyworm, Spodoptera litura, Kaburayaga, Yotoga, Tamanaginiwawa, Nikameiga, Kobunomeiga, Sankameiga, Nashio Shingui, Himadarameiga, Mamenomeiga, Ineztomushi, Cottontailed beetle, Potato moga, Scarlet crab Lepidopteran pests such as, pears, pears, peaches, peaches, grape scabs, chanhohosuga, konaga, and iga;

[0013] Tobacco whitefly, Onsius whitefly,
Aphid whiteflies, cotton aphids, snow aphids, apple aphids, apple aphids, peach aphids, radish aphids, saccharomyces aphids, bean aphids, komican aphids, citrus black aphids, grapevine aphids, green aphids, potato aphids, aphids Leafhopper, leafhopper, leafhopper, brown planthopper,
White-bellied planthopper, Leafhopper leafhopper, Leafhopper leafhopper, White leafhopper, Ruby beetle, Olive leaf scalebug, San Jose scalebug, Apple oyster scale, Akamaruka scalea, Akahosh scale scale scale, Yanone scale scale, Kuwaka scale scale, Green scale scale Hemiptera pests such as southern stink bugs, stag beetles, and nasi-gumbai;

[0014] Rice weevil, rice beetle, leaf beetle, beetle beetle, colorado beetle, beetle beetle, weevil, beetle beetle, sycamore, beetle beetle, bean weevil, azuki beetle, beetle beetle, beetle beetle, beetle
Lepidopteran pests such as beetles, beetles, beetles, tobacco beetles, beetles, beetles, beetles, and beetles;

Double-legged pests such as Culex pipiens, Culex pipiens, Aedes albopictus, Aedes albopictus, Rice mosquito fly, Soybean syllabus, Rice mosquito flies, Rice scallops, Musca domestica, Black flies, Onions, Papaver edulis and Citrus fruit flies.

Thrips insects, such as Thrips palmi, Thrips palmi, Thrips palmi, Thrips palmi, Thrips palmi, etc .;

[0017] Orthopterous insects such as black cockroaches, yamato cockroaches, brown cockroaches, German cockroaches, brown cockroaches, locust locusts, etc .;

Tick pests, such as N. spider mite, Kanzawa spider mite, Mandarin spider mite, Apple spider mite, Dermatophagoids mite, Rapeseed mite, Dermatophagoides pteronyssinus, Dermatophagoides, Dermatophagoides, Dermatophagoids, etc .; .

Diseases include diseases caused by discolored fungi, rot fungi, and fungi.

When the fungicidal and fungicidal composition of the present invention is actually applied, it can be made into a mixture of the above-mentioned two components or a single usual formulation for mixing in situ. In formulating the fungicidal and fungicidal composition of the present invention, there is no need for any special conditions, and by a method familiar with the art according to general agricultural chemicals, using an appropriate carrier, an emulsion, a wettable powder. , Pastes, powders, fine granules, flowables, microcapsules, oils, aerosols, smokers, bait and the like, and can be used for various purposes according to the respective purposes. .

The carrier as used herein refers to the synthesis or synthesis of liquids, solids, or gases that assist in reaching the active ingredient to the site to be treated and facilitate storage, transport, and handling of the active ingredient compound. Means a natural inorganic or organic substance.

Suitable solid carriers include, for example, montmorillonite, kaolinite, diatomaceous earth, terra alba, talc,
Vermiculite, gypsum, calcium carbonate, silica gel, inorganic substances such as ammonium sulfate, soybean flour, sawdust, flour, pectin, methylcellulose, sodium alginate, petrolatum, lanolin, liquid paraffin, lard,
Organic substances such as vegetable oils are included.

Suitable liquid carriers include, for example, aromatic hydrocarbons such as toluene, xylene, cumene, and solvent naphtha; paraffinic hydrocarbons such as kerosene and mineral oil; halogenated hydrocarbons such as methylene chloride and chloroform; , Methyl ethyl ketone, ketones such as cyclohexanone, dioxane, tetrahydrofuran,
Ethers such as ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, and propylene glycol monomethyl ether; esters such as ethyl acetate, butyl acetate, fatty acid butyl ester, and fatty acid glycerin ester; nitriles such as acetonitrile and propionitrile , Methanol, ethanol, isopropanol, n-propanol, alcohols such as ethylene glycol, dimethylformamide, dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone,
Water and the like.

Suitable gaseous carriers include nitrogen gas, carbon dioxide gas, dimethyl ether, propane gas, butane gas and the like.

Of course, the carriers mentioned here are not limited to these, and a wide range of carriers can be used. These may be used alone or in combination of two or more.

Further, in order to enhance the efficacy of the fungicidal and fungicidal composition of the present invention, the following auxiliary agents may be used alone or in combination according to the purpose, taking into account the dosage form of the preparation, the application scene, and the like. Can also be used.

Auxiliaries used for the purpose of emulsification, dispersion, spreading, wetting, binding, stabilization, etc. include water-soluble bases such as lignin sulfonates, alkylbenzene sulfonates,
Alkyl sulfates, polyoxyethylene alkyl aryl ethers, nonionic surfactants such as polyhydric alcohol esters, lubricants such as calcium stearate, wax, stabilizers such as isopropylhydrodiene phosphate, other methyl cellulose, carboxymethyl cellulose, Casein, gum arabic and the like.
However, these components are not limited to those described above. These may be used alone or as a mixture of two or more.

The fungicidal and fungicidal composition of the present invention imparts stability to light, heat, oxidation and the like. If necessary, an antioxidant or an ultraviolet absorber such as BH
T (2,6-di-t-butyl-4-methylphenol), BHA
By adding a suitable amount of a phenol derivative such as (butylhydroxyanisole), a bisphenol derivative, phenyl-α-naphthylamine, phenyl-β-naphthylamine, an arylamine of a condensate of phenetidine and acetone, or a benzophenone compound as a stabilizer. Thus, a composition having more stable effects can be obtained.

The insecticidally active compound represented by the above general formula (1) and the iodine fungicidally active compound represented by the general formula (1) used in the fungicidal and insecticidal composition of the present invention each contain 0.1% of said compound.
000001 to 95% by weight, preferably 0.0001 to 50% by weight. To apply the fungicidal and fungicidal composition of the present invention, the active ingredient is generally 0.001 to 5000 ppm, preferably 0.
Use at a concentration of 01 to 1000 ppm.

[0030]

EXAMPLES The composition of the present invention is described below by way of formulation examples.
The effect of the composition of the present invention will be described in detail by test examples,
These are specific examples, and the present invention is not limited by these. In the following, all “parts” are based on weight.

Preparation and Notation of Compound Represented by Formula (1) In the compound represented by Formula (1), R _{1 to} R
₅ are each a compound shown in the following Table 1, and manufactured by the method disclosed in JP-A-8-245322,
The compound names are shown below as [Compound 1] to [Compound 5], and these were used in the following Formulation Examples and Test Examples relating to the composition of the present invention.

[0032]

[Table 1]

Formulation Example 1 1 part of IPBC and 1 part of [Compound 1] were dissolved in 20 parts of xylene, and 78 parts of white kerosene were mixed and dissolved to prepare an oil.

Formulation Example 2 20 parts of DMTS and 10 parts of [Compound 2], 2 parts of sodium alkylnaphthalenesulfonate, 1 part of sodium ligninsulfonate, 5 parts of white carbon, 62 parts of diatomaceous earth,
The above was stirred and mixed to prepare a wettable powder.

Formulation Example 3 After dissolving 10 parts of IPBC and 5 parts of [Compound 3] in 60 parts of xylene, 10 parts of Solpol 355S (manufactured by Toho Chemical Co., Ltd., a surfactant) are mixed with stirring, and 15 parts of white kerosene are further added. ,
An emulsion was prepared.

Formulation Example 4 30 parts of DMTS, 10 parts of [Compound 5], 1 part of polyoxyethylene alkylphenyl ether and 39 parts of water were uniformly mixed and pulverized, and then 0.2 parts of xanthan gum and 19.8 parts of water were added.
And a flowable agent.

Next, test examples will be shown to prove the usefulness of the composition of the present invention. Test Examples 1-1 to 8 (Efficacy test against ticks) A solution prepared by dissolving 1 part of an iodine compound and 1 part of the compound represented by the general formula (1) in acetone was placed in each of three sets of glass petri dishes having a diameter of 9 cm. , The iodine compound and the compound represented by the general formula (1) were applied so that the added amount was 50 mg / m ² . Next, these were dried to remove acetone, and a dry film was formed. After that, 30 heads each of Dermatophagoides farinae, Dermatophagoides farinae, and Southern red mite were placed and left. Table 2 shows the state of life and death of these mites 48 hours later.

Comparative Example 1 (No Treatment) In Test Example 1, the same operation was performed without applying anything to the glass petri dish. Table 2 shows the results.

[0039]

[Table 2]

Test Examples 2-1 to 4 and Test Examples 3-1 to 4
(Efficacy test for mites) In Test Example 1, IPBC was used as the iodine compound.
And [Compound 1] or [Compound 5] as the compound represented by the general formula (1), and changing the mixing ratio thereof so that the respective amounts applied to the glass petri dish become the amounts shown in Table 3. And performed similarly. Table 3 shows the results.

Comparative Examples 2 to 4 In Test Example 1, the iodine compound IPBC
And only the compound represented by the general formula (1) [Compound 1] or [Compound 5] is used, and the same is applied so that the amount applied to the glass Petri dish is as shown in Table 3. I went to. Table 3 shows the results.

[0042]

[Table 3] In the test examples performed with the composition of the present invention, compared to those of Comparative Examples 2 to 4 performed using each alone, even a small amount of addition shows a higher mortality rate than it. . That is, it is understood that the composition of the present invention has an excellent synergistic effect.

Test Example 4 (Efficacy test on termites) A solution prepared by dissolving 1 part of IPBC and 1 part of [Compound 1] in acetone was placed in a glass petri dish having a diameter of 9 cm, and each of IPBC and [Compound 1] was 50 mg / m ^2. Was applied in such a manner as to be added. Next, this was dried to remove acetone, and a dry film was formed. After that, 20 Yamato termites were put in the container and allowed to contact the film for 1 minute. afterwards,
The test insects were transferred to another clean petri dish covered with filter paper that had been previously absorbed with water, and the number of struggling and dead animals was observed over time. Note that this test was performed at 20 ° C. Table 4 shows the results.

Test Examples 5-1 to 3 In the same manner as in Test Example 4 described above, the mixing ratio of IPBC and [Compound 1] was changed, and the respective amounts applied to the glass petri dishes were as shown in Table 4. Was. Table 4 shows the results
Shown in

Comparative Example 5 (No treatment) In Test Example 4, the same operation was performed without applying anything to the glass petri dish. Table 4 shows the results.

Comparative Examples 6 and 7 In the above-mentioned Test Example 4, when either IPBC or [Compound 1] was applied to a glass Petri dish,
The procedure was performed in the same manner as described above. Table 4 shows the results.

[0047]

[Table 4] The test examples performed with the present invention show a higher mortality even with a smaller amount than the comparative example performed using each of them alone. That is, it is understood that the composition of the present invention has an excellent synergistic effect.

Test Examples 6-1 to 8 (Efficacy test against mold) 2 parts of an iodine compound and 1 part of a compound represented by the general formula (1) were dissolved in acetone, and the solution was added to a potato dextrol agar medium. After adding and mixing so as to have the addition amounts shown in Table 5, each was poured into a petri dish having a diameter of 9 cm and hardened. Then, according to JIS-Z-2911, a mold suspension (Aspergillus niger, Penicillium.
(Citulinum, Resorbes nigricans, Cladosporium herbalum, and Ketomium glabosum). The change with time in this state was visually observed. Table 5 shows the results.

Comparative Examples 8 to 11 In the above test examples, no treatment was performed without any addition.
The same procedure was carried out using only IPBC, only [Compound 1], or only [Compound 5]. Table 5 shows the results.

[0050]

[Table 5] (Note 1) 3 ... No mold growth is observed in the inoculated area. 2 ... The area of the mold growing part observed in the inoculated part does not exceed 1/3 of the total area. 1 ... The area of the mold growing part observed in the inoculated part exceeds 1/3 of the total area.

Conventionally, an iodine compound is known as a compound having a high fungicidal and fungicidal effect. However, from Table 5, even when the composition of the present invention is used, its efficacy against mold has not been reduced at all. It can be seen that it still has a high bactericidal and fungicidal effect.

[0052]

As described above, the composition of the present invention comprising a compound represented by the general formula (1) and an iodine compound having a fungicidal and fungicidal activity is useful for various fungi, molds and various pests. In addition to exerting an accurate control effect, it exhibits an excellent synergistic effect, and an excellent effect can be obtained at a lower dose or a lower concentration.

Further, since each of the compounds constituting the composition of the present invention has extremely low toxicity to humans and animals, it can be safely used for various industrial raw materials or industrial products.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI (A01N 51/00 31:02) (A01N 51/00 47:06) (72) Inventor Masahiko Nakamura 1144 Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd.

Claims (2)

[Claims] 1. A compound of the general formula (1) (Wherein, R ₁ represents a hydrogen atom or a methyl group, R _2, R
₃ and R ₄ represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. A fungicidal and fungicidal composition comprising a compound represented by the formula (I) and an iodine compound having fungicidal and fungicidal activity. 2. An iodine compound having fungicidal activity is diiodomethyl-p-tolylsulfone, 3-iodo-2-
The fungicidal fungicide according to claim 1, which is selected from the group consisting of propynyl Nn-butyl carbamate, 2,3,3-triiodoallyl alcohol and 3-bromo-2,3-diiodo-2-propenyl carbonate. Composition.