JPH03220105A - Bactericidal composition - Google Patents

Abstract

PURPOSE:To obtain a bactericidal composition widely usable with a low dosage and a low damage due to agricultural chemicals and markedly effective even against a resistant bacterium, containing aralkylamine derivative and a bactericidal compound having an ergosterol biosynthesis-inhibiting activity as active ingredients. CONSTITUTION:An aralkylamine derivative expressed by formula I (R1 is halogen; R2 and R3 are respectively lower alkyl) or acid-added salt of said derivative and a bactericidal compound (e.g. triazimephone expressed by formula II or hexaconazole expressed by formula III) having an ergosterol biosynthesis- inhibiting activity are contained in the objective composition as active ingredients. Mixing ratio is 0.1-10 pts.wt., preferably 1-5 pts.wt. the latter compound to 1 pt.wt. the compound expressed by formula I. In using, said composition is used in preparing as powder, emulsion or wettable powder, etc. As the compound expressed by formula I, dl-5-chloro-6-methyl-4(alpha-ethyl-4- difluoromethoxybenzylamino)pyrimidine, etc., is exemplified.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a fungicidal composition containing an aralkylamine derivative or an acid addition salt thereof and a fungicidal compound having ergosterol biosynthesis inhibitory activity.

[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, compounds that simply have an effect are not immediately approved for use as agricultural chemicals.

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.

The disadvantage is that the chemical structure of such satisfactory bactericidal compounds is necessarily more complex than conventional ones, which makes their production costs higher than conventional ones. Therefore, it is necessary to develop a drug that has a higher lotus killing effect than conventional products and can be used at a lower dose.

Due to the current state of pesticide development, the amount of pesticides used is becoming as low as possible. One way in that direction is not only to find compounds that have a higher bactericidal effect than conventional ones, but also to further reduce the amount of bactericidal compounds used by adding substances that can increase that effect. There are possible ways.

The bactericidal composition of the present invention was discovered for the first time with such an intention, and as the present inventors have already shown, the aralkylamine derivative in the bactericidal composition is particularly suitable for use in cereal udon powder. It is a compound that has an extremely high bactericidal effect in controlling diseases and rust (Patent application No. 1-2).
01245), the substance that enhances the bactericidal effect of its derivatives is a bactericidal compound that has ergosterol biosynthesis inhibitory activity.

[Problem that the invention seeks to solve]

An object of the present invention is to provide a fungicidal composition containing an aralkylamine derivative or an acid addition salt thereof and a fungicidal compound having ergosterol biosynthesis inhibitory activity.

[Means for solving problems]

As a result of intensive research to solve the above-mentioned problems, the present inventors have discovered that a sterilizing agent obtained by combining the above-mentioned aralkylamine derivative or its acid addition salt with a sterilizing compound having ergosterol biosynthesis inhibitory activity. The efficacy of the compositions is greatly increased over their efficacy alone (allowing the use of their bactericidal compounds to be significantly reduced) and is highly effective against bacteria that have developed resistance to these single compounds. They found that it is effective and has a wide sterilizing spectrum, and have completed the present invention.

That is, the present invention provides an aralkylamine derivative or an acid addition salt thereof represented by the following formula: (wherein R3 represents a halogen atom; R2 and R1 each represent a lower alkyl group) and ergosterol biosynthesis inhibitory activity. bactericidal compound N with
I) It relates to a sterilizing composition characterized by containing the following.

The present invention will be explained in detail below.

In the above compound (I), 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.

Among such compounds, the following three compounds (compounds 1 to 3) are most preferable.

(Compound l) 'dA-5-chloro-6-methyl-4-(α-ethyl-
4-difluoromethoxybenzylamino)pyrimidine (
n” ” 1.5471) (Compound 2) dl-5-chloro-6-methyl-4-(α-methyl-4
-difluoromethoxybenzylamino)pyrimidine (
+o, p, 56-58°C), (Compound 3) dl-5-chloro-6-nityl-4-(α-methyl-4
-difluoromethoxybenzylamino)pyrimidine (n
30'' 1.5442) 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, 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-) luenesulfonic acid, etc.), saccharin, and the like.

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

Compound (1) and its acid addition salt used in the present invention can be easily produced by, for example, compound (I) as described below 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 reaction and removing the solvent.

(Z represents a leaving group) Examples of the bactericidal compound (n) having ergosterol biosynthesis inhibitory activity used in the present invention include azole-based and morpholine-based compounds, but preferably The following 1o compounds (compounds A-J) can be mentioned.

(Hereinafter, blank space) (In the formula, R,, Rt and R8 have the same meanings as above, and the sterilizing composition of the present invention is prepared by blending the compounds (I) and (It) in a conventional manner, for example, It is used by preparing a composition such as a powder, an emulsion, a fine granule, a granule, a wettable powder, an oily suspension, or an aerosol. Preferably, compound (II) is added to the mixture.

The active ingredient in the fungicidal composition of the present invention may include compound (U) in a ratio of 0.1 to IO parts by weight, preferably 1 to 10 parts by weight, per 1 part by weight of compound (1).
A ratio of 5 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 granules, 0.5 to 5% by weight for oils, 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 and examples, but these are not intended to limit the scope of the present invention.

Reference Example 1 [dffi-5-chloro-6-methyl-4(
α-ethyl-4-difluoromethoxybenzylamino)
Synthesis of pyrimidine (compound 1)] 4,5-dichloro-6
-Methylpyrimidine (0°9g), di-α-ethyl-
4-difluoromethoxybenzylamine (1.0g) and triethylamine (1mf) were dissolved in toluene (20rr+
A catalytic amount of 4-(N,N-dimethylamino)pyrimidine was added, and 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 = 15:1), and the target compound 1, which was a colorless oil, was isolated.
1.2g of was obtained.

Reference Example 2 (dffi-5-chloro-6-methyl-4(
α-methyl-4-difluoromethoxybenzylamino)
Synthesis of pyrimidine (compound 2)] In Reference Example 1, d
i! By carrying out the same procedure as in Reference Example 1 using dj2-α-methyl-4-difluoromethoxyhensylamine instead of -α-ethyl-4-difluoromethoxybenzylamine, 1.1 g of the target compound 2 was obtained. .

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

Example 1 [Preparation of hydrating agent] A bactericidal compound having ergosterol biosynthesis inhibitory activity (
10 parts by weight of each of Compounds A-J), 88 parts by weight of kaolin, and 2 parts by weight of Neoperex powder (trade name: manufactured by Kao Atlas) were uniformly mixed and then ground to obtain each wettable powder.

Example 2 [Control efficacy test (preventive effect) against wheat rust] A predetermined amount of the wettable powder prepared in Example 1 was mixed with a surfactant (0,
Each solution of compounds A-J was obtained by diluting with water containing 0.01%). Then, each of these solutions and compound 1.2 or 3
A sterilizing composition was prepared by mixing the following, and was used in subsequent tests at a predetermined active ingredient concentration as shown in Table 1.

Ten wheat plants (variety: wheat) per pot were grown into seedlings at the 1.5-leaf stage in plastic flower pots with a diameter of 6 cm.

For each of the predetermined active ingredient concentration solutions of the fungicidal composition prepared as described above,
Sprayed on young seedlings in pots.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then a spore suspension (7X 10' spores/m2) of wheat rust (Puccinia recondita) was sprayed uniformly onto the plants.

After 71 days of contact, put it in a constant temperature room (20'C, 100% relative humidity).
After being covered for 0 hours, the plants were grown in a glass greenhouse (20''C) for one week, and the extent of wheat rust lesions that appeared on the first leaves was examined.

Evaluation of drug efficacy was made 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 (in addition, in the column of drug damage,
r No 1 indicates no drug damage. ).

(Hereafter, blank space) Chapter ■ Table (continued) Table (continued) Test compound cap ■ Bolt. , Example 3 [Control efficacy test (preventive effect) against barley powdery mildew] A predetermined amount of the wettable powder prepared in Example 1 was mixed with a surfactant (0,
Each solution of compounds A-J was obtained by diluting with water containing 0.01%). And each of these solutions and compound l, 2 or 3
A sterilizing composition was prepared by mixing the following, and was further used in subsequent tests at a predetermined active ingredient concentration as shown in Table 2.

Ten barley plants (variety: black wheat) per pot were grown into young plants at the 1.5-leaf stage in plastic flower pots with a diameter of 6 cm.

For each of the predetermined active ingredient concentration solutions of the fungicidal composition prepared as described above, 20 ml per pot was added to each
Sprayed on young seedlings in pots.

After spraying, cultivation was carried out in a glass greenhouse (20°C) for 2 days, and then barley powdery mildew (Ery
The plant was inoculated by uniformly sprinkling a conidial suspension of S. siphe graminis.

After inoculation, the barley was grown in a glass greenhouse (20"C) for one week and the degree of powdery mildew lesions that appeared on the first leaves was investigated. The evaluation method is shown in Table 2.

Table 2 Table 2 (continued) Table 2 (continued) Example 4 [Control efficacy test (preventive effect) against cucumber powdery mildew] A predetermined amount of the wettable powder prepared in Example 1 was added to a surfactant (0%). ，
Each solution of compounds A-J was obtained by diluting with water containing 0.01%). Then, each of these solutions and compound 1.2 or 3
A sterilizing composition was prepared by mixing the following, and was further used in subsequent tests at a predetermined active ingredient concentration as shown in Table 3.

A pot containing one grown seedling was prepared by sowing seeds of cucumber (variety: Sagami Hanjiro Seishi) in a plastic flower pot with a diameter of 6 cm and growing them for 15 days.

For each of the predetermined active ingredient concentration solutions of the fungicidal composition prepared as described above, 20 ml per pot was added to each
Sprayed on young seedlings in pots.

After spraying, the cells were cultivated in a glass greenhouse (20 °C) for 2 days, and then a spore suspension of cucumber powdery mildew (resistant or sensitive to compounds A and D was used at 10'/ml) Seedlings were evenly sprayed and inoculated at 1 m2 per pot.

After inoculation, the seeds were grown in a glass greenhouse (20°C) for 10 days.
The degree of cucumber powdery mildew lesions that appeared on the second leaf was investigated, and the control rate (%) of the chemical was calculated using the following formula.

The results are shown in Table 3 (in the column of drug damage, r
"No" indicates no drug damage, and r-repression 1 indicates growth inhibition. ).

3rd table bikinmono (GW @ atmosphere 2゜m) ■I soy sauce table soy secret■
The bactericidal effect is significantly enhanced compared to using each of Natsume Table 3 (Continued) alone, the dosage can be reduced accordingly, and no chemical damage occurs.

Claims (1)

[Claims] 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. 1. A bactericidal composition comprising an aralkylamine derivative or an acid addition salt thereof represented by the following formula and a bactericidal compound having ergosterol biosynthesis inhibitory activity.