JPH04178306A - Fungicide composition containing polyoxyethylene sorbitol fatty acid ester - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a disinfectant composition containing a polyoxyethylene sorbitol fatty acid ester and an aralkylamine derivative or an acid addition salt thereof having disinfectant activity.

[Conventional technology]

The development of new fungicides is significant because long-term use of drugs can lead to the emergence of resistance to the drugs in symbolic organisms.

Therefore, attempts have been made to synthesize compounds that have various fungicidal effects, but today it is not possible to simply use a compound that has an effect as an agricultural chemical.

In other words, since environmental pollution has become a major social issue, in addition to the sterilizing effect, use must also be met for safety against living things (humans, animals, fish, etc.). We are now in a situation where it is necessary to synthesize a compound that can simultaneously satisfy the following.

Therefore, it is necessary to develop a compound that has a higher bactericidal effect than conventional bactericidal compounds because the chemical structure is more complex than conventional bactericidal compounds, which has the disadvantage of higher manufacturing costs than conventional ones. There is.

Due to the current state of pesticide development, the amount of pesticides used is becoming as low as possible. One way to go in that direction is not only to find a compound that has a higher bactericidal effect than before, but also to add a substance that enhances that effect, thereby further reducing the amount of the bactericidal compound used. It will be done.

The fungicidal composition of the present invention was discovered for the first time with such an intention, and the fungicidal compound used in the present invention in the fungicidal composition is, as already shown by the present inventors. In particular, it is an aralkylamine derivative or an acid addition salt thereof that is extremely effective in controlling powdery mildew and rust of cereals (Japanese Patent Application No. 1-201245).
The substance used in the present invention to enhance the bactericidal effect of the compound is whether it is used as an adjuvant in bleaching aids, lubricants, antistatic agents, detergents, emulsifiers, etc., or whether it has a bactericidal effect in itself. Polyoxyethylene sorbitol fatty acid ester.

[Problems to be Solved by the Invention] An object of the present invention is to provide a disinfectant composition containing a polyoxyethylene sorbitol fatty acid ester and an aralkylamine derivative which is a disinfectant compound.

[Means for solving problems]

As a result of intensive research in order to solve the above problems, the present inventors have found that polyoxyethylene sorbitol fatty acid ester, which is extremely safe, is mixed into the aralkylamine derivative, which is the above-mentioned bactericidal compound, as a pesticidal activity enhancer. The present inventors have discovered that by doing so, the efficacy of the bactericidal compound can be greatly enhanced and the amount of the bactericidal compound used can be significantly reduced, leading to the completion of the present invention.

That is, the present invention provides an aralkylamine derivative represented by the following formula: (In the formula, R1 represents a halogen atom; R2 and R3 each represent a lower alkyl group; the carbon atom marked with * represents an asymmetric carbon atom) or its acid addition salt and polyoxyethylene sorbitol fatty acid ester (I[
) The present invention relates to a disinfectant composition containing the following.

The present invention will be explained in detail below.

In the above compound (I), Examples of halogen atoms include fluorine atoms and chlorine atoms.

Bromine atom and iodine atom can be mentioned, but chlorine atom or fluorine atom is preferable.

Examples of the lower alkyl group include C3-4 linear or branched alkyl groups, preferably methyl and ethyl groups.

The most preferred among such compounds are: dl-5-chloro-6-methyl-4-(α-ethyl-
4-difluoromethoxybenzylamino)pyrimidine (m, p, below 50-51°C0, referred to as compound 1).

)・dl-5-chloro-6-methyl-4-(α-methyl-4-difluoromethoxybenzylamino)pyrimidine (m, p, 56-58°C.Hereinafter referred to as compound 2)・
d/-5-chloro-6-nityl-4-(α-methyl-4
-difluoromethoxybenzylamino)pyrimidine (n 1.5442.Hereinafter, referred to as compound 3.

) Since compound (I) has an amino group, it can easily form an acid addition salt.

Examples of acids that form such acid addition salts include inorganic acids (hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid).

phosphoric acid), carboxylic acids (formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid.

aconitic acid, etc.), organic sulfonic acids (methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.), and saccharin.

Since the carbon atom marked with * is an asymmetric carbon atom, compound (I) includes individual optical isomers, racemic compounds, or mixtures thereof.

Compound (I) and its acid addition salt used in the present invention can be easily produced as follows, for example, according to the description in Japanese Patent Application No. 1-201245.
Moreover, the acid addition salt thereof can be easily obtained by adding an appropriate acid to the reaction solution after the completion of the reaction and removing the solvent.

(Hereinafter, blank spaces) (In the formula, R1, R2, and R3 have the same meanings as above; X represents a leaving group; carbon atoms marked with * represent asymmetric carbon atoms) A compound that enhances pest control activity. A certain polyoxyethylene sorbitol fatty acid ester (II) is preferably one represented by the following formula: (wherein the sum of each integer of a, b, c, d, e and f is 30 to 60) (For example, Kao products such as Odol 440, Rheodol TW-L 120, Rheodol TW-0120, Rheodol TW-S120, Rheodol MS-165, etc.) are good; Rheodol 440 is more preferable.

Rheodol 440 is a mixture of polyoxyethylene sorbitol fatty acid esters listed below.

(In the formula, the sum of each integer of a, b, c, d, e, and f is 40.) The fungicide composition of the present invention is obtained by blending the compounds (I) and (II) above by a conventional method. For example, the composition is prepared into a powder, an emulsion, a single fine granule, a wettable powder, an oily suspension, or an aerosol.

The compounding method is preferably such that compound (I[) is added to a spray liquid containing compound (I) at the time of use.

The active ingredient in the fungicidal composition of the present invention can be compounded in a ratio of 1 to 100 parts by weight of compound (It) per 1 part by weight of compound (I), but preferably 5 to 100 parts by weight.
A ratio of 60 parts by weight is preferable. And the total active ingredient content is
Usually 1 to 50% by weight for emulsions and 0.3 to 2% for powders.
5% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for 9 granules, usually 0.5 to 5% by weight for oily powders,
For aerosols, it is usually 0.1 to 5% by weight.

These preparations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, or the water surface of paddy fields, depending on the purpose.
Alternatively, it can be applied directly for various purposes.

(Hereinafter, in the margins) [Example] The present invention will be described in more detail below using reference examples, examples, and test examples, but these do not limit the scope of the present invention.

Reference Example 1 [dl-5-ri-4-6-methyl-4-(α-ethyl-
4-difluoromethoxybenzylamino)pyrimidine (
Synthesis of compound l)] 4.5-dichloro-6-methylpyrimidine (0.9g)
, Gar α-ethyl-4-difluoromethoxybenzylamine (1,0 g) and triethylamine (1 m77) were dissolved in toluene (20 ml) and a catalytic amount of 4-(N,N
-dimethylamino)pyrimidine was added and heated under reflux for 8 hours.

After the reaction, the reaction solution was washed with water and dried with anhydrous sodium sulfate.
Toluene was distilled off under reduced pressure.

The obtained oil was isolated by column chromatography (Wako Gel C-200° elution with toluene:ethyl acetate=15:1) to obtain 1.2 g of the desired compound 1 as a colorless oil.

Reference Example 2 (dl-5-chloro-6-methyl-4-(α-methyl-
4-difluoromethoxybenzylamino)pyrimidine (
Synthesis of Compound 2)] In Reference Example 1, a-α-ethyl-4-difluoromethoxybenzylamine was replaced with α-methyl-4-
By carrying out the same procedure as in Reference Example 1 using difluoromethoxybenzylamine, 1.1 g of the target compound 2 was obtained.
Obtained.

Reference example 3 (dl-5-chloro-6-nityl-4-(α-methyl-
4-difluoromethoxybenzylamino)pyrimidine (
Synthesis of Compound 3)] In Reference Example 1, 4,5-dichloro-6-ethylpyrimidine was used instead of 4,5-dichloro-6-methylpyrimidine, and a-α-ethyl-4-difluoromethoxybenzylamine was synthesized. Instead, 1.2 g of the target compound 3 was obtained by carrying out the same procedure as in Reference Example 1 using a-α-methyl-4-difluoromethoxybenzylamine.

Example 1 [Preparation of hydrating powder] Reference example 1. 20 parts by weight of each of compounds 2 and 3.

78 parts by weight of kaolin and 2 parts by weight of Neoperex powder (trade name: manufactured by Kao ■) were uniformly mixed and then ground to obtain each wettable powder.

Example 2 [Preparation of emulsion] 5 parts by weight of each of the compounds of Reference Example 1.2 or 3.

30 parts by weight of Odol 440 as compound (II),
10 parts by weight of Ageli Seal P-300 (trade name: manufactured by Kao ■) and 55 parts by weight of xylene were added and uniformly dissolved to obtain each emulsion.

Test Example 1 [Control efficacy test (preventive effect) against wheat rust] Ten wheat plants (variety: Kovushi wheat) were grown per pot in plastic flower pots with a diameter of 6 cm, and the test was carried out on young plants at the 1.5 leaf stage. A predetermined amount of the hydrating powder of Compound 1, 2, or 3 prepared in Example 1 was diluted with water, and a predetermined amount of Rheodol 440 as the potency enhancer Compound (II) was added thereto to prepare each mixture. did.

This was sprayed on 3 pots at 20 doses per pot.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then a spore suspension (7 x 105 spores/yJ) of Puccinia recondita was uniformly sprayed and inoculated onto the plants.

After inoculation, incubate in a constant temperature room (20°C, 100% relative humidity) for 20 days.
After aging, the plants were grown in a glass greenhouse for one week, and the extent of wheat rust lesions that appeared on the first leaves was examined.

The drug effect was evaluated by comparing the degree of lesions in the untreated area.
6 stages (0: whole disease affected, 1: lesion area approximately 60%,
2: Lesion area is approximately 40%, 3: Lesion area is approximately 20%, 4: Lesion area is 10% or less, 5: No lesion). The results are shown in Table 1.

Table 1 Test Example 2 [Control efficacy test (preventive effect) against barley powdery mildew] Ten barley plants (variety: black wheat) were grown per pot in plastic flower pots with a diameter of 6 cm, and A predetermined amount of the hydrating powder of Compound 1, 2, or 3 prepared in Example 1 was diluted with water, and a predetermined amount of Rheodol 440 as the potency enhancer Compound (n) was added to the seedling. Each mixture was prepared.

This was sprayed on 3 pots at 20 rILl per pot.

After spraying, cultivation was carried out in a glass greenhouse for 2 days, and then barley powdery mildew (Erysiphe) obtained from diseased leaves was grown.
A conidial suspension of C. graminis was evenly sprinkled onto the plant to inoculate it.

After inoculation, the plants were grown in a glass greenhouse (20°C) for one week, and the extent of barley powdery mildew lesions that appeared on the first leaves was examined. The results of the evaluation of drug efficacy are shown in Table 2 using the same evaluation method as Test Example 1.

Table 2 [Effects of the Invention] The disinfectant composition comprising the aralkylamine derivative or its acid addition salt of the present invention and polyoxyethylene sorbitol fatty acid ester has a significantly more bactericidal effect than the aralkylamine derivative or its acid addition salt alone. The drug is strengthened, and the dosage can be reduced accordingly.

Claims (1)

[Claims] (1) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1 represents a halogen atom; R^2 and R^
3 each represents a lower alkyl group; carbon atoms marked with * represent asymmetric carbon atoms) A sterilizer characterized by containing an aralkylamine derivative or its acid addition salt represented by: agent composition.