JPH04173706A - Bactericidal composition containing polyethylene glycol fatty acid ester - Google Patents

Abstract

PURPOSE:To provide the title composition markedly enhanced in the activity of the bactericidal compound as a component, thus markedly reduced in its dose, comprising an aralkylamine derivative having bactericidal activity or its acid-adduct salt and a polyethylene glycol fatty acid ester. CONSTITUTION:The objective composition comprising (A) an aralkylamine derivative (or its acid-adduct salt) of formula I (R<1> is halogen; R<2> and R<3> are each lower alkyl; C* is asymmetric carbon atom) having markedly high effects on controlling, in particular, of grain powdery mildew and rust and (B) 1-100 (pref. 5-60) pts.wt., per pt.wt. of the component A, of a polyethylene glycol fatty acid ester of formula II (R is 1-20C alkyl or alkenyl; (n) is integer, 30-60) of extremely high safety as bactericidal activity enhancer. As the bactericidal activity of the component A is strongly enhanced in the present composition, it also leads to enable its dosage to be reduced correspondingly.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a disinfectant composition containing a polyethylene glycol 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, environmental pollution has become a major social problem, and in addition to its bactericidal effect, it must be safe for living things (humans, animals, fish, etc.) before it can be used. We are currently in a situation where it is necessary to synthesize a compound that can satisfy these requirements at the same time.

Therefore, since the chemical structure is more complex than the conventional bactericidal compounds, the manufacturing cost is higher than the conventional ones. need to be developed.

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 to find a compound that has a higher bactericidal effect than before, and to add a substance that increases that effect, thereby 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 in cereals (Japanese Patent Application No. 1-201245).
The substance used in the present invention to enhance the bactericidal effect of the compound is used as an adjuvant in bleaching aids, lubricants, antistatic agents, detergents, emulsifiers, etc., but it has no recognized bactericidal effect in itself. It is a polyethylene glycol fatty acid ester that cannot be used.

[Problem that the invention attempts to solve]

An object of the present invention is to provide a disinfectant composition containing a polyethylene glycol 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-mentioned problems, the present inventors have discovered that an extremely safe polyethylene glycol fatty acid ester is mixed with the aralkylamine derivative, which is the above-mentioned fungicidal compound, as a pesticidal activity enhancer. The inventors have discovered that 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 an acid addition salt thereof and a polyethylene glycol fatty acid ester represented by the following formula:% formula%() (wherein R represents an alkyl group or alkenyl group of 01 to 2o; n represents an integer of 30 to 60) The present invention relates to a disinfectant composition characterized by 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.

Mention may be made of bromine atom and iodine atom, preferably chlorine atom or fluorine atom.

Examples of the lower alkyl group include C, -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-difluoromethoxybensylamino)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, below 56-58°00, referred to as compound 2).

)・dl-5-chloro-6-nityl-4-(α-methyl-4-difluoromethoxyhensylamino)pyrimidine compound (I) easily forms acid addition salts because it has an amino group. I can do it.

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.

Examples include aconitic acid), organic sulfonic acids (methanesulfonic acid, benzenesulfonic acid, p-1-luenesulfonic 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 described below, for example, in accordance with 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.

(In the formula, Rl, R2 and R3 have the same meanings as above,
X represents a leaving group; the carbon atom marked with * represents an asymmetric carbon atom) The compound (I[) that enhances the control activity is not particularly limited as long as it is represented by this compound formula; C+
o to 2o alkyl group or alkenyl group, and n is 3
May be an integer from 0 to 60; preferably R or C
an alkyl group or alkenyl group of I2 to I11, and n
or an integer between 30 and 50 (for example, Kao's products Emanon 1112, Emanon 3199.
Emanone 4110 is more preferred; Emanon 4110 is more preferred.

Emanone 4110 is the following polyethylene glycol fatty acid ester.

RCOO(CH2C) (20) ,,H (wherein R is C
+g represents an alkyl group or alkenyl group of 18; n represents an integer of 40 to 50) The disinfectant composition of the present invention is prepared by blending the compounds (I) and (II) in a conventional manner, For example, it is used by preparing a composition such as 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 (II) 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 may be compound (n) in a ratio of 1 to 100 parts by weight, preferably 5 to 6 parts by weight, per 1 part by weight of compound (I).
A ratio of 0 parts by weight is preferable. The total active ingredient content is usually 1 to 50% by weight for emulsions and 0.3 to 25% for powders.
The amount is usually 1 to 90% by weight for wettable powders, 0.5 to 5% by weight for single granules, 0.5 to 5% by weight for oil solutions, and 0.1 to 5% by weight for aerosols.

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.

〔Example〕

Hereinafter, the present invention will be explained in more detail by reference examples, examples, and test examples, but these are not intended to limit the scope of the present invention.

Reference Example 1 (Synthesis of dn-5-chloro-6-methyl-4-(α-ethyl-4-difluoromethoxybenzylamino)pyrimidine (compound 1)) 4.5-dichloro-6-methylpyrimidine (0, 9g)
, #-α-ethyl-4-difluoromethoxybenzylamine (1,0 g) and triethylamine (1-) were dissolved in toluene (20 m/) and a catalytic amount of 4-(N,N-dimethylamino)pyrimicine was added. The mixture was 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°, eluted with toluene:ethyl acetate = 15 L), and the target compound 1, which was a colorless oil, was isolated.
1.2g of was obtained.

Reference Example 2 Cdl-5-chloro-6-methyl-4-(α-methyl-
4-difluoromethoxybenzylamino)pyrimidine (
Synthesis of Compound 2)] In Reference Example 1, R-α-methyl-4 was used instead of dl-α-ethyl-4-difluoromethoxybenzylamine.
-Reference Example 1 using difluoromethoxybenzylamine
By carrying out the same procedure as above, the target compound 2 is converted to 1.1
I got g.

Reference example 3 (dl-5-chloro-6-nithyl-4-(α-
Synthesis of methyl-4-difluoromethoxybenzylamino)pyrimidine (compound 3)] In Reference Example 1, 4.5
-4.5- instead of dichloro-6-methylpyrimidine
By carrying out the same procedure as in Reference Example 1 using dichloro-6-ethylpyrimidine and using d-α-methyl-4-difluoromethoxyhensylamine instead of dl-α-ethyl-4-difluoromethoxybenzylamine, 1.2 g of the target compound 3 was obtained.

Example 1 [Preparation of hydrating powder] 20 parts by weight of each of the compounds of Reference Example 1.2 or 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 Emanone 4110 as the compound (It), Agelisil P-300 (trade name: Kao Corporation) 10
parts by weight and 55 parts by weight of xylene were added and uniformly dissolved,
Each emulsion was obtained.

Test Example 1 [Control efficacy test (preventive effect) against wheat rust] 10 wheat plants (variety: Triticum trifolium) 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 1st and 5th leaf stages. 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 Emanone 4110 as the potency enhancer compound (n) 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/-) of wheat rust (Puccinia recondita) was sprayed uniformly 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.

(The following is a blank space) 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 1.5 leaves were grown per pot. 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 Emanone 4110 as the potency enhancer Compound (II) was added to the seedlings at the stage. A mixed solution of each of the added substances was prepared.

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

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

After inoculation, it was grown in a glass greenhouse (20℃) for one week, and the
The extent of barley powdery mildew lesions that appeared on leaves was investigated.

The results of the evaluation of drug efficacy are shown in Table 2 using the same evaluation method as Test Example 1.

〔Effect of the invention〕

The disinfectant composition of the present invention comprising an aralkylamine derivative or an acid addition salt thereof and a polyethylene glycol fatty acid ester has a significantly stronger disinfectant effect than an aralkylamine derivative or an acid addition salt thereof alone, and the dosage can be reduced accordingly. It is something.

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) and an aralkylamine derivative or its acid addition salt represented by the following formula: RCOO(CH_2CH_2O)_nH (in the formula, R is C_1_ _2_0 represents an alkyl group or alkenyl group; n represents an integer of 30 to 60).