JPH03197403A - Fungicide composition - Google Patents

Abstract

PURPOSE:To obtain a fungicide composition having improved activity and, accordingly, effective at a low rate of application by mixing a phosphonic acid ester having extremely high safety as a controlling power promoting agent to an aralkylamine derivative known as a fungicidal compound. CONSTITUTION:The objective fungicide composition contains 1 pt.wt. of a compound of formula I (R1 is halogen; R2 and R3 are lower alkyl) and 1-100 pts.wt. of a compound of formula II [X is (OCH2CH2)n-O-R4 ((n) is 1-40; R4 is 8-30C alkyl-substituted phenyl); Y is OH or X]. The composition is used in the form of powder, emulsion, granule, wettable powder, oil suspension, aerosol, etc., by mixing the compound of formula I and the compound of formula II, preferably by adding the compound of formula II to a spraying liquid containing the compound of formula I before use. The preparation is diluted to a proper concentration and sprayed to the leaf and stalk of plant, soil, surface of paddy field, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a fungicidal composition containing a fungicidal compound and a phosphonic acid ester.

[Conventional technology]

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

Therefore, attempts have been made to synthesize compounds that have various fungicidal effects, but today it is no longer possible to simply use a compound that has an effect as a pesticide.

In other words, since environmental pollution has become a major social problem, in addition to the sterilizing effect, it is not allowed to be used unless it satisfies the safety requirements for living things (humans, animals, fish, etc.). We are currently in a situation where it is necessary to synthesize a compound that can satisfy these requirements at the same time.

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 possible means 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 fungicide composition of the present invention was discovered for the first time with such an intention, and as the present inventors have already shown, the fungicide compound in the fungicide composition is particularly effective against cereals. It is an aralkylamine derivative that is extremely effective in controlling powdery mildew and rust (patent application No. 1-2).
The substance that enhances this effect is a phosphonic acid ester that is used as an adjuvant in bleaching aids, lubricants, antistatic agents, detergents, emulsifiers, etc., but has no bactericidal effect by itself. be.

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

[Means for solving problems]

As a result of intensive research to solve the above-mentioned problems, the present inventors have found that by mixing an extremely safe phosphonic acid ester as a pest control activity enhancer with the above-mentioned bactericidal compound, an aralkylamine derivative. 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.

13= That is, the present invention provides a compound or acid addition salt represented by the following formula: (wherein, R represents a halogen atom; R2 and R3 each represent a lower alkyl group) and the following formula: The present invention will be described in detail.

In the above compound (1), examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, but preferably a chlorine atom or a fluorine atom, and the lower alkyl group has a number of carbon atoms. Examples include 1 to 4 linear or branched alkyl groups, with methyl and ethyl groups being preferred.

The most preferred among such compounds is dρ-5-chloro-6-methyl-4-(α-ethyl-4
-difluoromethoxybenzylamino) [wherein, X is -
(OCHz CHz) I, 0-R4, where n represents an integer of 1 to 40; R4 has a carbon atom number of 8 to
Represents 30 alkyl groups or alkyl-substituted phenyl groups. ); Y represents -OH or X. ) A disinfectant composition containing a phosphonic acid ester or a salt thereof.

Pyrimidine (hereinafter abbreviated as compound 1).

1 1.5471), d! -5-chloro-6-methyl-4-(α-methyl-4
-difluoromethoxybenzylamino)pyrimidine (hereinafter abbreviated as compound 2. m, p, 56-58°C), dff1-5-chloro-6-nityl-4-(α-meduthyl-4-difluoromethoxybenzyl amino)pyrimidine (hereinafter abbreviated as compound 3).

n 1.5442) It is.

Since compound (1) 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, etc.);
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.), saccharin, and the like.

Since the carbon atom marked with * is an asymmetric carbon atom, compound (1) 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 reaction and removing the solvent.

(In the formula, Rr, Rt, and R3 have the same meanings as above; Z represents a leaving group.) In the fungicide composition of the present invention, compound (II), which is a pesticidal activity enhancer, is present in its molecule. Since it has a phosphoric acid group, it may be used as is or after being neutralized with a basic compound.

Such basic compounds include alkali metals (e.g., caustic soda, caustic acid, etc.), organic bases (e.g., ammonia, monomethylamine, dimethylamine,
trimethylamine, monoethylamine, diethylamine, triethylamine, monoethanolamine, jetanolamine, triethanolamine, pyridine, morpholine, etc.).

The compound (n) is not particularly limited as long as it is represented by this compound formula, but for example, General Antw.
ine & Film Corp (G, A,
GAPACLO-529, PH-, a product of F.
510, PE-610, RM-510, RM710,
RP-710, R5-410SR3-610, RA-6
Among them, GAFACL
O-529 is preferred.

GAFACLO-529 is a mixture of the sodium salts of the monoesters and diesters listed below.

Monoester: Diester: (n is 5 or 6) The fungicide composition of the present invention is prepared by blending the compounds (I) and (n) above in a conventional manner, and forming the composition into, for example, a powder, an emulsion, or a fine granule. It is used by preparing compositions such as powders, granules, wettable powders, oily suspensions, or aerosols.

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

The active ingredient in the fungicide composition of the present invention can be compounded in a proportion of 1 to 100 parts by weight of compound (II) per 1 part by weight of compound (I), preferably 5 to 100 parts by weight.
A ratio of 60 parts by weight is preferable. Therefore, the total active ingredient content is usually 1 to 50% by weight for emulsions and 0.3% for powders.
-25% by weight, usually 1-90% by weight for wettable powders, usually 0.5-50% by weight for granules, usually 0.5-5% by weight for oils, and usually 0.1-5% 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 do not limit the scope of the present invention.

Reference Example 1 (dff-5-chloro-6-methyl-4(α-
Synthesis of ethyl-4-difluoromethoxybenzylamino)pyrimidine (compound 1)] 4.5-dichloro-6-methylpyrimidine (0°9g), dffi-α-ethyl-
4-difluoromethoxybenzylamine (1.0 g) and triethylamine (1 mI!) were dissolved in toluene (20 mI!).
To j2)? It was dissolved, a catalytic amount of 1-(N,N-dimethylamino)pyrimidine was added, and the mixture was heated to reflux for 8 hours.

After the reaction, the reaction solution was washed with water, anhydrous sulfuric acid, and dried over IJum, and toluene was distilled off under reduced pressure.

The resulting oil was isolated by column chromatography (Wako gel (elution with -200° toluene:acetic acid 15:1)) to obtain 1.2 g of the desired compound 1 as a colorless oil.

Reference example 2 (dI!, -5-chloro-6-methyl-4(
α-methyl-4-difluoromethoxyhensylamine)
Synthesis of pyrimidine (compound 2)) In Reference Example 1, d
By carrying out the same procedure as in Reference Example 1 using dffα-methyl-4-difluoromethoxyhensylamine instead of p-α-ethyl-4-difluoromethoxybenzylamine, 1.1 g of the target compound 2 was obtained.

Reference example 3 (d, e-5-chloro-6-nityl-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-6ethylpyrimidine and using dp-α-methyl-4-difluoromethoxybenzylamine instead of dp, -α-ethyl4-difluoromethoxybenzylamine, 1.2 g of the target compound 3 was obtained.

Examples 1 to 3 [Preparation of wettable powders] 20 parts by weight of each of the compounds of Reference Example 15.2 or 3, 78 parts by weight of kaolin, and Neoperex powder (trade name:
2 parts by weight (manufactured by Kao Atlas) were mixed uniformly and then ground to obtain each wettable powder. Examples 4 to 6 [Preparation of emulsions] 5 parts by weight of each of the compounds of Reference Example 1.2 or 3, the compound (
■) 30 parts by weight of GAFAC1,0-529, 10 parts of Ageli Seal P-300 (product name: manufactured by Kao Atlas)
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: Kovushi wheat) were grown per pot in plastic flower pots with a diameter of 6 cm, and the test was carried out on seedlings at the 1.5 leaf stage. A predetermined amount of the hydrating powder of Compound 1.2 or 3 prepared in Examples 1 to 3 was diluted with water, and a predetermined amount of GAFACLO-529 as the potency enhancer Compound (II) was added thereto. A liquid was prepared.

This is ■20. Three pots were sprayed at mA doses.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then a spore suspension (7 x 10' spores/mβ) of Puccinia recondita was spray-inoculated uniformly onto the plants.

After inoculation, incubate in a constant temperature room (20'C1 relative humidity 100%) for 20 minutes.
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: disease all over, 1: lesion area approximately 60%,
2: Lesion area is approximately 40%, 3: Lesion area is approximately 20%, 4: Lesion area is 10% or less, and 5 (no lesions). The results are shown in Table 1 = 13 4 .

-17- Test Example 2 [Control efficacy test against barley powdery mildew (preventive effect)] Ten barley plants (variety: black wheat) were grown per pot in plastic flower pots with a diameter of 6 cm, and young barley at the 1°5 leaf stage were grown. A predetermined amount of the hydrating powder of Compound 1.2 or 3 prepared in Examples 1 to 3 was diluted with water, and a predetermined amount of GAFACLO-529 was added to the plant body as a compound (It) as a potency enhancer. A mixed solution of each of the added substances was prepared.

This is 20mI per pot! I sprayed it on 3 pots in batches.

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.

[Effects of the Invention] The bactericidal composition comprising compound (1) and compound (II) of the present invention has a bactericidal effect significantly enhanced compared to compound (I) alone, 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. ) and the following formula: ▲Mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X is -(OCH_2CH_2)_n-O-R_
4 (where n represents an integer from 1 to 40; R_4
represents an alkyl group having 8 to 30 carbon atoms or an alkyl-substituted phenyl group. ); Y represents -OH or X. ] A disinfectant composition containing a phosphonic acid ester or a salt thereof.