JPH05155718A - Seed disinfectant - Google Patents

Abstract

PURPOSE:To obtain a seed disinfectant by combining a pyridonecarboxlic acid derivative with a compound effective for powdery mildew, rust, blast, etc., having a high antimicrobial spectrum, showing stably controlling effects on diseases with a small amount. CONSTITUTION:A pyridonecarboxlic acid derivative, preferably at least one of flumiquine of formula I, norfloxacin of formula II, ciprofloxacin of formula III, pipemidic acid of formula IV, piromidic acid of formula V, nalidixic acid of formula VI, oxolinic acid of formula VII, cinoxacin of formula VIII, its alkali metal salt and its lower alkyl ester is combined with 2(4-chlorobenzyl)-5- isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol of formula IX to give the objective seed disinfectant. This disinfectant shows high effects on various infectious diseases, has higher effects then those obtained by single use of each component and can reduce an amount of active ingredient. Diseases causing problems during a raising seedling period are suppressed.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to flumequine, norfloxacin, ciprofloxacin, pipemidic acid, pyromidic acid, nalidixic acid, oxolinic acid, sinoxacin, or alkali metal salts thereof or lower alkyl esters thereof. At least one of them, 2-
(4-chlorobenzyl) -5-isopropyl-1- (1
H-1,2,4-triazol-1-ylmethyl) -1
-A seed disinfectant containing cyclopentanol as an active ingredient.

[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.

On the other hand, seed disinfection is extremely effective for controlling diseases during the seedling raising period. Conventionally, in order to control seed-borne diseases, benomyl agents, thiphonate methyl agents, thiuram agents, copper agents, triflumizo have been 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 (EBI agents) such as triflumizole agents and pefrazoate agents have begun to be used as agents effective against benzimidazole drug-resistant bacteria, but ergosterol biosynthesis inhibitors are filamentous fungi. Although it has a high effect on the disease, it cannot be expected to have an effect on the bacterial disease, so that the antibacterial spectrum is narrower than that of the conventional mixture, and unsatisfactory points remain. Further, as a bacterial disease agent, calcium hypochlorite agents, copper agents, etc. 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 was a problem that the concentration was high and it was difficult to prepare the 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, the present inventor can achieve the above-mentioned object by using a combination of two specific active ingredients and have a synergistic effect on the disease controlling effect. The present invention has been completed and the present invention has been completed. Therefore, the seed disinfectant of the present invention comprises a flumequin of structural formula (I) of formula 10, a norfloxacin of structural formula (II) of formula 11, a ciprofloxacin of structural formula (III) of chemical formula 12, and a structure of chemical formula 13. The pipemidic acid of formula (IV), the pyromidic acid of structural formula (V) of Chemical formula 14, the nalidixic acid of structural formula (VI) of Chemical formula 15, the oxolinic acid of structural formula (VII) of Chemical formula 16, the structural formula of chemical formula ( VIII) sinoxacin, or an alkali metal salt thereof, or a lower alkyl ester thereof (hereinafter, referred to as a pyridonecarboxylic acid derivative in the present specification means a compound represented by the chemical formula 10 to chemical formula 17 or an alkali metal salt thereof). Salt or a lower alkyl ester), and 2- (4-chlorobenzyl) -5-isopropyl-1- (1H-1,2,4-) of the structural formula (IX) bird Tetrazole-1-ylmethyl) -1-cyclopentanol (hereinafter compound (A), characterized in that it contains to as) as an active ingredient.

[Chemical 10]

[Chemical 11]

[Chemical 12]

[Chemical 13]

[Chemical 14]

[Chemical 15]

[Chemical 16]

[Chemical 17]

[Chemical 18]

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 above structural formula (IX), and
The compound described in Japanese Patent Publication No. 93574, which exhibits an excellent control effect against powdery mildew, rust, fruit scab, scab, rice scab, blast, sesame leaf blight, etc. of various crops. It is known.

On the other hand, it is known that the pyridonecarboxylic acid derivative, which is another active ingredient of the seed disinfectant of the present invention, is effective as a bacterial agent. For example, it has been widely used as a therapeutic agent for bacterial infectious diseases and as a preventive and therapeutic agent for bacterial infectious diseases of livestock and cultured fish. As a fungicide for agricultural and horticultural use, an oxolinic acid of the above structural formula (VII), which is one of the pyridonecarboxylic acid derivatives, has been put to practical use as a seed disinfectant for paddy rice. Japanese Patent Publication 57-4804
No. 2 discloses a series of pyridonecarboxylic acid compounds effective as agents for controlling plant bacterial diseases. However,
Mixing the pyridonecarboxylic acid derivative and the compound (A),
It was not known to be used as a seed disinfectant.

According to the present invention, these pyridonecarboxylic acid derivatives, preferably at least one of flumequine, oxolinic acid or sinoxacin, and compound (A).
When and are used as active ingredients, the antibacterial spectrum including bacterial disease and filamentous fungal disease is widened, and a stable effect is also exhibited against resistant bacteria, and the control effect is synergistic as compared with the case where they are used alone. Is excellent. In the seed disinfectant of the present invention, the mixing ratio of the compound (A) and the pyridonecarboxylic acid derivative is 1: 0.1 to 1: 200 by weight.
Is used, and preferably in the range of 1: 0.5 to 1:15.

To use the seed disinfectant of the present invention, the above-mentioned active ingredients can be used as they are, but they are usually mixed with a carrier and used as a formulation. In addition, if necessary, various pharmaceutical auxiliaries such as surfactants, wetting agents,
Add a fixing agent, a thickener, a stabilizer, etc. to obtain a wettable powder, a powder,
It can be used by formulating into a dosage form such as 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,
Solid carrier such as walnut powder, urea, ammonium sulfate, fine powder or granular material such as synthetic hydrous silicon oxide, aromatic hydrocarbon such as xylene and methylnaphthalene, isopropanol,
Examples thereof include alcohols such as ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, 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. When seed dressing is used, an appropriate amount of the preparation is usually 0.05 to 5% of the dry seed weight, but such an amount is suitable for the form of the preparation and the type of seeds of the crop to be treated. It can change depending on Furthermore, by mixing and using the seed disinfectant of the present invention with other fungicides such as hydroxyisoxazole, a wider range of seed infectious diseases can be controlled. Also, thiuram, kasugamycin, thiabendazole, carbendazim, captan,
Probenazole, benomyl, thiphonate methyl,
It can also be mixed with triflumizole, prochloraz, pefurazoate 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)
smiyabeanus), stupa seedling disease (Gibbere)
lla fujikuroi), bacterial blight (Pse)
udomonas glumae), bacterial wilt disease (P
Pseudomonas plantarii, brown streak (Pseudomonas avenae), rice koji (Ustilaginoidea virens), leaf blight (Septoria tritic) of wheat
i), brown stripe wilt (Leptospheria no)
dorum), lintel smut (Tilletia c)
aries), naked smut (Ustilago trit)
ici), Fusarium sp., Cochliobolus sativus, Barley leaf spot (Helminthosporium)
Ramineum), naked smut (Ustilagon)
uda), net blotch disease (Pyrenophora tere)
s), cloud disease (Rhynchosporium seca)
lis), blight (Septoria sp.), hard smut (Ustilago avenae), rye smut (Tilletia carriers), and the like.

[0014]

EXAMPLES The present invention will be described in detail below with reference to test examples. The compounds (1) to (9) are the compounds shown in Table 1, respectively.

[Table 1] Formulation Example 1 (powder) 1 part of compound (A), 3 parts of compound (1), 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) 0.1 part of compound (A), 20 parts of compound (1), 5 parts of lignin sulfonate, 3 parts of alkyl sulfonate and 71.9 parts of diatomaceous earth are pulverized and mixed well. By doing, the active ingredient 2
A wettable powder containing 0.1% was obtained.

Formulation Example 3 (Suspension) 6 parts of compound (A), 3 parts of compound (1), 0.5 part of polyoxyethylene nonylphenyl ether, 0.5 part of xanthan gum, polycarboxylic acid type polymer activator (Demolition E
P (registered trademark)) 1.5 parts, ethylene glycol 8 parts,
80.5 parts of water was mixed and wet-milled until the particle size of the mixture became 5 μm or less to obtain a suspension containing 9% of the active ingredient.

Test Example 1 (Seed Disinfection Effect Test against Rice Blight Bacterial Disease) Rice Blight Bacteria (Pseudomonas gluma)
e) A suspension containing inoculated paddy prepared according to Formulation Example 3
Immersion treatment was carried out for a period of time, and then 2 plastic pots were seeded in 2 pots of 4.5 g 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 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.

[Formula 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 Equation 2. In formula 2, X and Y represent the morbidity (index) when two preparations of the active compound are applied separately, and E represents the morbidity expected when the mixture of the active compounds is applied.

[Formula 2] If the actually observed morbidity is smaller than the expected morbidity (E), which holds in the equation 2, it means that there is a synergistic effect.

The results are shown in Table 2.

[Table 2] In Table 2, 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 with a wettable powder prepared according to Formulation Example 24 for 24 hours, and then placed in a plastic pot filled with nursery soil per pot. 4.5 g each was seeded in 2 pots. Then, after keeping the seedling incubator at 30 ℃ for 3 days, in the greenhouse 14
It was cultivated for a day, the disease state was investigated, and the morbidity was calculated by the 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]

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

[Formula 4] The results are shown in Table 3.

[Table 3] In Table 3, ¹⁾ indicates E obtained by the equation 4.

Test Example 3 (Simultaneous Control Test of Rice Bacterial Seedling Disease and Bacterial Blight Disease 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 paddy infected with both diseases.
A wettable powder prepared according to Formulation Example 2 was used for immersion treatment for 24 hours, and then seeded in a plastic pot filled with seedling-growing soil at 4.5 g per pot in 2 pots.
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 degree of morbidity was calculated by 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.

[0023]

[Formula 5] The results are shown in Table 4.

[Table 4]

[0024]

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.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 43/60 8930-4H 43/90 8930-4H 53/00 A 8930-4H

Claims (1)

[Claims] 1. Flumequin of structural formula (I) of chemical formula 1, norfloxacin of structural formula (II) of chemical formula 2, structural formula (III of chemical formula 3)
) Ciprofloxacin, chemical formula 4 of pipemidic acid of formula (IV), chemical formula 5 of formula (V) pyromidic acid, chemical formula 6 of formula (VI) nalidixic acid, chemical formula 7 (VII) ), An oxolinic acid represented by the formula (8), a synoxacin represented by the structural formula (VIII) represented by Chemical formula 8, an alkali metal salt thereof, or at least one of lower alkyl esters thereof, and
2- (4-chlorobenzyl) -5-isopropyl-1- (1H-1,2,4-triazole-in the structural formula (IX) of
A seed disinfectant containing 1-ylmethyl) -1-cyclopentanol as an active ingredient. [Chemical 1] [Chemical 2] [Chemical 3] [Chemical 4] [Chemical 5] [Chemical 6] [Chemical 7] [Chemical 8] [Chemical 9]