JPH05105605A - Seed disinfectant - Google Patents

Abstract

PURPOSE:To obtain a seed disinfectant capable of simultaneously controlling a seed infectious filamentous fungal disease and bacterial disease at a low dose. CONSTITUTION:The objective seed disinfectant contains (A) 2-(4-chlorobenzyl)-5- isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol of formula I capable of exhibiting excellent controlling effects on Powdery mildew and Rust of various kinds of crops, Rust and Scab of fruit trees and 'Bakanae' disease, Blast and Helminthosporium leaf spot of a rice plant and (B) 2-bromo-2- nitropropane-1,3-diol of formula II which is effective for bacterial diseases as active ingredients. The both ingredients are used in a weight ratio of the components A:B of 1:0.5 to 1:100, preferably 1:0.5 to 1:20.

Description

Detailed Description of the Invention

[0001]

The present invention relates to 2- (4-chlorobenzyl) -5-isopropyl-1- (1H-1,2,4-
The present invention relates to a seed disinfectant containing triazol-1-ylmethyl) -1-cyclopentanol and 2-bromo-2-nitropropane-1,3-diol as active ingredients.

[0002]

2. Description of the Related Art With the spread of mechanical transplantation of paddy rice, it has become important to grow healthy seedlings during the box raising period. In recent years, in addition to rice scab seedling disease, blast disease, and sesame leaf blight caused by filamentous fungi, the occurrence of bacterial diseases such as rice blight bacterial disease, bacterial wilt disease, and brown stripe disease is a major problem in recent years. Is becoming. JP-A-1-93574 discloses 2- (4-chlorobenzyl) -5-isopropyl-1- (1H-1,
2,4-triazol-1-ylmethyl) -1-cyclopentanol is described, and powdery mildew of various crops, rust, red scab of fruit trees, black scab, rice sprouting disease of rice, blast of rice, sesame leaf blight. It is known to show an excellent control effect against diseases and the like. Further, Merck Index, 11th edition, page 219, describes 2-bromo-2-nitropropane-1,3-diol, and further, JP-A-60-105606.
Japanese Patent Publication No. 2-bromo-2-nitropropane-1,3.
-Diols and ergosterol biosynthesis inhibitors (EBI
Agent): A synergistic effect on Lendtes travea when combined with prochloraz is described.

By the way, seed disinfection is extremely effective for controlling diseases during seedling raising. Conventionally, in order to control seed-borne diseases, benomyl agents, thiphonate methyl agents, thiuram agents, copper agents, triflumizo are used. -Pills, pefurazoates or mixtures thereof have been used. However, the conventionally used seed disinfectant has a problem. For example, regarding benzimidazole drugs that have been widely used in the past, resistant bacteria have appeared in some of the pathogenic bacteria, and it has been reported that the control effect is reduced. In recent years, ergosterol biosynthesis inhibitors such as triflumizole and pefurazoate have begun to be used as effective drugs against benzimidazole-resistant bacteria, but ergosterol biosynthesis inhibitors are highly effective against filamentous fungal disease. However, the antibacterial effect could not be expected against the bacterial disease, so that the antibacterial spectrum was narrower than that of the conventional mixture, and unsatisfactory points remained. Further, as a bacterial disease agent, calcium hypochlorite agents, copper agents and the like have been put to practical use, but the effect is not sufficient, the selectivity is poor, and further mixing with several agents is not possible. There are problems such as high concentration and difficulty in preparing a solution.

[0004]

Therefore, in addition to filamentous fungal diseases, it is effective against bacterial diseases, has a broad antibacterial spectrum, and simultaneously controls these diseases, and is stable against the above resistant bacteria. It was required to develop a low dose of seed disinfectant having the above-mentioned control effect. The present invention has been made in view of such circumstances. Therefore, an object of the present invention is to provide a seed disinfectant having a broad antibacterial spectrum and a stable disease control effect against the above-mentioned resistant bacteria and having a low dose.

[0005]

Means for Solving the Problems As a result of repeated studies by the present inventors, when two specific active ingredients, which have not been known to be used as a seed disinfectant in the past, are used in combination, It has been found that the above-mentioned objects can be achieved and that they have a synergistic effect on disease control, and the present invention has been completed. Therefore, the seed disinfectant of the present invention is 2
-(4-Chlorobenzyl) -5-isopropyl-1-
(1H-1,2,4-triazol-1-ylmethyl)
Containing 1-cyclopentanol (hereinafter, referred to as "compound (A)") and 2-bromo-2-nitropropane-1,3-diol (hereinafter, referred to as "compound (B)") as active ingredients Is characterized by.

The present invention will be described in detail below. Compound (A) which is one of the active ingredients of the seed disinfectant of the present invention
Is represented by the following structural formula (I), and is excellent in powdery mildew, rust, red scab, scab, fruit scab disease, blast, sesame leaf blight, etc. of various crops. It is known to show a controlling effect.

[Chemical 1]

On the other hand, the compound (B), which is another active ingredient of the seed disinfectant of the present invention, is represented by the following structural formula (II) and is known to be effective as a bacterial disease agent. It is what has been.

[Chemical 2]

According to the present invention, when these compound (A) and compound (B) are used in combination as an active ingredient, they show a broad antibacterial spectrum and a stable effect against resistant bacteria, and their control effects are independent. It is remarkably excellent as compared with the case where it is used, and the effect is synergistic. In the seed disinfectant of the present invention, the mixing ratio of the compound (A) and the compound (B) is in the range of 1: 0.5 to 1: 100 by weight, preferably 1: 0.5 to 1:20. Used in the range of.

In order to use the seed disinfectant of the present invention, the above-mentioned active ingredients can be used as they are, but usually, they are mixed with a carrier and made into a formulation for use. In addition, if necessary, various formulation auxiliary agents, for example, surfactants,
A wetting agent, a sticking agent, a thickening agent, a stabilizer and the like may be added to the composition to prepare a dosage form such as a wettable powder, a powder and a flowable agent.

In the seed disinfectant of the present invention, when the above-mentioned active ingredient is mixed with a carrier, its content is usually in the range of 0.1 to 80% by weight. The carrier of the above formulation, kaolin, attapulgite, bentonite, acid clay, bilophyllite, talc, diatomaceous earth, calcite,
Walnut powder, urea, ammonium sulfate, solid carriers such as fine powder or granules of synthetic hydrous silicon oxide, xylene, aromatic hydrocarbons such as methylnaphthalene, alcohols such as isopropanol, ethylene glycol, cellosolve,
Ketones such as acetone, cyclohexanone, and isophorone,
Examples include vegetable oils such as soybean oil and cottonseed oil, and liquid carriers such as dimethyl sulfoxide, acetonitrile and water.

Surfactants used for emulsification, dispersion, wet extension, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts, Naphthalene sulfonic acid formaldehyde condensate, anionic surfactant such as polycarboxylic acid type polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, etc. Examples include nonionic surfactants. As a formulation auxiliary agent, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, C
Examples include MC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), xanthan gum and the like.

When the seed disinfectant of the present invention is used for seed treatment, the formulation is diluted with water to give an active ingredient concentration of 80 to 500.
A 0 ppm solution can be prepared, and seeds can be dipped, sprayed, or seed-dressed in this solution for use. The amount used in the case of seed dressing is usually 0.05 to 5% of the dry seed weight as the amount of the formulation, but the amount used also depends on the form of the formulation and the type of seeds to be treated. Can change. Furthermore, the seed disinfectant of the present invention,
By mixing with other fungicides such as hydroxyisoxazole, a wider range of seed-borne diseases can be controlled. Further, it can be mixed with thiuram, kasugamycin, thiabendazole, carbendazim, captan, probenazole, benomyl, thiphonate methyl, triflumizole, prochloraz, pefrazoate and the like.

A specific example of a disease for which the seed disinfectant of the present invention is effective is rice blast (Pyricularia).
oryzae), sesame leaf blight (Cochliobolu)
s miyabeanus), fool seedling disease (Gibber)
ella fujikuroi), bacterial blight (Ps)
eudomonas glumae), bacterial seedling blight (Pseudomonas plantarii), brown stripe disease (Pseudomonas avenae), rice scab (Ustilaginoidea viren)
s), wheat leaf blight (Septoria tri)
tici), brown stripe wilt (Leptospheria)
nodorum), lintel smut (Tilleti)
a carriages, naked smut (Ustilago t)
ritici), seedling blight (Fusarium s)
p. ), Iris (Cochliobolus sati)
vus), barley leaf spot (Helminthosp)
orium gramineum), naked smut (Ust
ilago nuda), net blotch (Pyrenopho)
ra teres), cloud disease (Rhynchospor)
ium secalis), wilt disease (Septoria)
sp. ), Red smut (Ustilago avena)
e), rye smut (Tilletia cari)
es) etc.

[0014]

EXAMPLES The present invention will be described in detail below with reference to test examples. Formulation Example 1 (powder) 1 part of compound (A), 3 parts of compound (B), 40 parts of clay,
By thoroughly mixing and pulverizing 56 parts of the talc portion, a powder containing 4% of the active ingredient was obtained.

Formulation Example 2 (wettable powder) Compound (A) 1.8 parts, compound (B) 1.5 parts, lignin sulfonate 5 parts, alkyl sulfonate 3 parts, diatomaceous earth 88.7 parts are often used. By pulverizing and mixing, a wettable powder containing 3.3% of the active ingredient was obtained.

Formulation Example 3 (Suspension) 6 parts of compound (A), 10 parts of compound (B), 0.5 part of polyoxyethylene nonylphenyl ether, 0.5 part of xanthan gum, polycarboxylic acid type polymer activator (Demol EP (registered trademark)) 1.5 parts, ethylene glycol 8
16 parts of water and 73.5 parts of water are mixed, and wet-milled until the particle size of the mixture is 5 microns or less.
A suspension containing 10% was obtained.

Test Example 1 (Seed Disinfection Effect Test against Rice Blight Bacterial Disease) Rice Blight Bacteria (Pseudomonas gluma)
e) The inoculated paddy was treated with the suspension prepared according to Formulation Example 3 to
Immersion treatment was performed for 4 hours, and then, 4.5 g per pot was sown in two plastic pots filled with seedling raising soil. Then, the mixture was kept at 30 ° C. for 3 days in a nursery, and then cultivated in a greenhouse for 14 days, the disease state was investigated, and the morbidity was calculated by the following formula (1). Note that a morbidity of 0 means that no disease has occurred, and a morbidity of 100 means that the disease-free control group is the same.

[Equation 1]

In order to help explain the synergistic effect between the active compounds used in this test, the results of the above test are shown by RS Colbey, Weeds, Vol. 15, pp. 20-22. (1967
Year)). The expected morbidity E (index) was calculated according to the following formula (2). In the formula (2), X and Y represent the morbidity (index) when the two preparations of the active compound are applied separately, and E is the expected morbidity when the mixture of the active compounds is applied. Represent

[Equation 2] If the actually observed morbidity is smaller than the expected morbidity (E) obtained by the equation (2), it means that there is a synergistic effect.

The results are shown in Table 1.

[Table 1] In Table 1, 1) indicates E obtained by the equation (2).

Test Example 2 (Seed disinfection effect on rice seedlings infected with rice scab seedling fungus) Rice scab seedling fungus (Gibberella fujiku)
roi) was inoculated at the flowering stage of rice and infected rice was soaked for 24 hours with a wettable powder prepared according to Formulation Example 2 and then placed in two plastic pots filled with seedling cultivation soil. , 4.5 g were seeded per pot. Then, the mixture was kept at 30 ° C. for 3 days in a nursery, then cultivated in a greenhouse for 14 days, the disease state was investigated, and the morbidity was calculated by the following formula (3). Note that a morbidity of 0 means that no disease has occurred, and a morbidity of 100 means that the disease-free control group is the same.

[0021]

[Equation 3] In the following formula (4), X and Y represent the morbidity (index) when two preparations of the active compound are separately applied, and E is the morbidity expected when the mixture of the active compounds is applied. Represents.

[Equation 4] If the actually observed morbidity is smaller than the expected morbidity (E) obtained by the equation (4), it means that there is a synergistic effect.

The results are shown in Table 2.

[Table 2] In addition, in Table 2, 1) indicates E obtained by the equation (4).

Test Example 3 (Simultaneous Control Test of Rice Bacterial Seedling Disease and Rice Bacterial Blight by Seed Disinfection) Rice scabbed seedling fungus (Gibberella fujiku)
roi) against infected paddy obtained by inoculating rice during flowering period,
Pseudomonas gluma
e) was inoculated to prepare diseased rice infected with both diseases. Immersion treatment was performed for 24 hours with a wettable powder prepared according to Formulation Example 2 and then seeded in two plastic pots filled with seedling cultivation soil at 4.5 g per pot. Then, the mixture was kept at 30 ° C. for 3 days in a nursery, and then cultivated in a greenhouse for 14 days, the disease state was investigated, and the morbidity was calculated by the following formula (5). Note that a morbidity of 0 means that no disease has occurred, and a morbidity of 100 means that the disease-free control group is the same.

[0024]

[Equation 5]

The results are shown in Table 3.

[Table 3]

[0026]

EFFECTS OF THE INVENTION The seed disinfectant of the present invention exerts a high effect against various seed-borne diseases, and exceeds the effects when each component is used alone, and can reduce the amount of active ingredient. Is. In addition, the antibacterial spectrum is wide,
It is possible to control filamentous fungal diseases and bacterial diseases at the same time, reduce the work for disinfecting seeds, and at the same time, suppress the occurrence of diseases that cause problems during the seedling raising period.

Claims (1)

[Claims] 1. 2- (4-chlorobenzyl) -5-isopropyl-1- (1H-1,2,4-triazole-1)
A seed disinfectant comprising -ylmethyl) -1-cyclopentanol and 2-bromo-2-nitropropane-1,3-diol as active ingredients.