JP2916342B2 - Soil disease controlling composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[Object of the Invention]

[0002]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a soil disease controlling composition comprising a soil disease controlling agent and a microbial agent.

[0003]

2. Description of the Related Art Soil diseases caused by soil pathogens in various crops have been a major problem in crop cultivation or agricultural management due to the magnitude of the damage and difficulty in controlling them.

In recent years, from the viewpoint of rationalization of cultivation and distribution,
Intensive cultivation with highly durable facilities and equipment or cultivation of various crops has been specialized, and the number of cases where a single crop is continuously cultivated on the same soil is increasing in abundance.

[0005] Due to such a trend, soil diseases frequently occur in institutional cultivation and open-field cultivation, causing a great deal of damage to crop cultivation, and sometimes there is no harvest at all.

[0006] Fusarium, picium, Aphanomyces, Rhizoctonia, and the like are known as typical soil pathogens causing such soil diseases.

[0007] At present, 3-hydroxy-5-methylisoxazole (hereinafter referred to as compound A) is widely used as a drug which is capable of controlling a variety of soil diseases caused by various soil pathogens and having high environmental safety. Commonly used. For example, it is used for rice and various crops for seedling wilt caused by picium and fusarium fungi, fusarium wilt of various crops, and sugar beet seedling wilt due to Aphanomyces fungi and the like. Compound A can control these soil diseases not only by directly treating the soil, but also by treating the seed. For example, the seed treatment of Compound A shows a high control effect on the seedling blight of sugar beet caused by Aphanomyces or Pythium, and the dressing of this compound is widely used in Japan and European countries. It is also known that compound A has an effect of enhancing physiological activity such as promoting plant root vigor and promoting growth. In Japan, methods of treating compound A on rice seeds directly sown in flooded soil are widely used. It has been known that it has an effect of stabilizing seedlings.

The calcium salt of compound A is disclosed in
In JP-38148, it is known to have the same activity as compound A against various crop diseases. Further, the calcium salt of compound A has a low volatility as compared with compound A, and is therefore advantageous as a seed treatment agent in this respect as well.

Further, in a hydroponic cultivation or the like, compound A and its salt also exhibit algicidal activity against A. aeruginosa.

[0010]

However, since compound A is rapidly biodegraded by soil microorganisms in soil, this is a factor limiting the residual effectiveness. This is known from the Sankyo Institute Annual Report, Vol. 25, pp. 42-45.

If the treatment amount is greatly increased in order to extend the residual effect, especially in the case of seed treatment, it may cause harmful effects such as suppressing the growth of the plant or delaying the emergence. A compound that is a calcium salt of compound A (hereinafter, referred to as compound C) is advantageous because it has less phytotoxicity when treated with seeds than compound A, but it may still cause phytotoxicity if the treatment amount is greatly increased. Therefore, it is difficult to extend the residual effect by greatly increasing the throughput. Therefore, depending on the use scene, such a compound A
In addition, there is a demand for enhancing the control effect by compensating for the lack of residual effect of compound C.

The present inventors have conducted intensive studies to solve these problems. As a result, the compound A contains a highly safe antimicrobial agent which suppresses the growth of soil microorganisms that decompose compound A and contains the compound A. Not only greatly enhances the residual effect of the compound A, but also exerts a high control effect that cannot be expected by preventing the decomposition of compound A alone, and completed the present invention.

[Structure of the Invention]

[0014]

SUMMARY OF THE INVENTION The present invention is a soil disease controlling composition containing 3-hydroxy-5-methylisoxazole or a salt thereof, and a microbial agent.

The salt of compound A is described in JP-B-48-38148.
And those known in the official gazette,
For example, sodium salt, potassium salt, calcium salt, magnesium salt, ammonium salt, preferably calcium salt, most preferably,

[0016]

Embedded image

Calcium salt dihydrate of compound A (hereinafter referred to as compound D). The metal atom or the like in these salts is substituted with the hydrogen atom of the hydroxyl group at the 3-position of the isoxazole ring of compound A. Compound D is
1 equivalent of calcium hydroxide and 2 equivalents of compound A are added to water, heated and dissolved at about 80 ° C., filtered while hot, the filtrate is cooled to about 0 ° C., and the precipitated crystals are collected by filtration. It is prepared by drying.

The antimicrobial agents to be used include those used as highly safe industrial fungicides and fungicides, and those used as agricultural germicides. Can be used.

Examples of industrial antimicrobial agents include fiber antibacterial and deodorant agents, wood preservative and antimicrobial agents, antibacterial and antimicrobial agents for paints, antibacterial and antimicrobial agents for leather, slime control agents, water treatment agents, and pool disinfectants. , An anti-algae agent, a preservative and preservative for chips and pulp, and the like.

Examples of the antimicrobial agent include formaldehyde, glyoxal, succinic dialdehyde,
Aldehydes such as 5-pentanedial; 2,5-
Dimethoxytetrahydrofuran, 5-halo-5-nitrodioxane (eg, 5-bromo-5-nitrodioxane), 2-halo-N-hydroxymethylacetamides (eg, 2-chloro-N-hydroxymethylacetamide), 1 -Hydroxymethyl-5,5-dimethylhydantoin, hexamethylenetetraamide, halogenated 1-
(3-haloallyl) -3,5,7-triaza-1-azoniaadamantane (eg, 1- (3-chloroallyl)-
3,5,7-triaza-1-azonia adamantanchloride), 1,3-bis (hydroxymethyl) -5,5-
Dimethyl-2,4-imidazolidinedione, 4,4-dimethyl-1,3-oxazolidine, hexahydro-1,
Aldehyde releasing compounds such as 3,5-tris (2-hydroxyethyl) -S-triazine; 2-bromo-2-
Formula R ^a as nitro-1,1-propanediol
-C (NO ₂₎ in ^{X-CH (OH) -R b} ( wherein, X represents a halogen atom, R ^a and R ^b indicates C ₁ -C ₆ alkyl group, hydroxy group, a hydrogen atom, a halogen atom A) a halogen-substituted nitro alcohol compound as represented by:
Formula _{^{R c -N + Me 2 -CH 2}} -Ph X - ( wherein,
X represents a halogen atom; Ph represents a phenyl group;
^c represents a C ₁₂ -C ₁₄ alkyl group); a quaternary ammonium salt having 1 to 6 carbon atoms having an aryl substituent such as benzoyloxymethanol; Lipophilic weak acids such as benzoic acid and its esters (alkyl esters such as n-propyl ester, aralkyl esters such as benzyl ester); substituted with aryl groups such as o-phenylphenol Phenols such as phenol; isothiazole-3 (2H)
-One, 1,2-benzisothiazole-3 (2H)-
On, 5-halo-2-methylisothiazole-3 (2
H) --ones (e.g., 5-chloro-2-methyl-isothiazole -3 (2H) - on, 2-C ₁ ~C ₁₀ alkyl isothiazole -3 (2H) --ones (e.g., 2-methyl iso Isothiazolones such as thiazol-3 (2H) -one); 2,4,5,6-tetrahaloisophthalonitrile (eg, 2,4,5,6-tetrachloroisophthalonitrile), haloxylenol ( Benzene or pyridine derivatives containing a halogen atom such as, for example, p-chloro-m-xylenol), halocresol (eg, p-chloro-o-cresol, p-chloro-m-cresol); tetrahydro-3,5- dimethyl-2H-1,3,5 thiadiazoline-2-thione, bis (dimethylthiocarbamoyl) disulfide, CS ₂ emission reduction, such as N- methyl dithiocarbamate Things; alkyl guanidine (e.g., dodecyl guanidine), bis [5- (halophenyl) - biguanide] hexane 2 hydrogen chloride salt (e.g., bis [5- (p
-Chlorophenyl) -biguanide] hexane dihydrochloride) and guanidines; haloacetamide (eg, chloroacetamide, bromoacetamide), 2,2-dihalo-3-nitrilopropionamide (eg, 2,2 Halogen-substituted amides such as -dibromo-3-nitrilopropionamide); copper hydroxide, copper sulfide,
An organic or inorganic copper agent such as copper-8-quinolate;
As compounds such as 10-10'-oxybis-10H-phenoxyarsine; 2- (4-thiazolyl) -1H
Other compounds such as -benzimidazole, N- (dichlorofluoromethylthio) phthalimide, N, N-dimethyl-N '-(dichlorofluoromethylthio) sulfamide:

Of the above, preferably, 1,5-pentanedial (hereinafter referred to as compound B-1), 2,5-dimethoxytetrahydrofuran (hereinafter referred to as compound B-2),
Glyoxal (hereinafter referred to as compound B-3), benzalkonium chloride (hereinafter referred to as compound B-4), 1,2-benzisothiazolin-3-one (hereinafter referred to as compound B-5), cupric hydroxide (hereinafter referred to as compound) B-6), p-
Chloro-m-xylenol (hereinafter referred to as compound B-7), p-chloro-o-cresol (hereinafter referred to as compound B-8)
N-propyl p-hydroxybenzoate (hereinafter referred to as compound B-9), tetrahydro-3,5-
Dimethyl-2H-1,3,5-thiadiazine-2-thione (hereinafter, referred to as compound B-10), and more preferably, compound B-1 and compound B-5. In the present invention, one or more of these can be used in combination.

The soil disease controlling composition of the present invention is prepared by blending compound A or a salt thereof with the above-mentioned antimicrobial agent by a conventional method to prepare a composition such as a powder, liquid, granule, wettable powder and the like. To use. These may be treated by mixing with fungicides, insecticides, fertilizers, soil conditioners and the like.

The active ingredient in the soil disease controlling composition of the present invention can be prepared by adding 0.01 to 10 parts by weight of an antimicrobial agent to 1 part by weight of compound A. A ratio of 0.1 to 1 part by weight is good. The total content of the active ingredient relative to the total amount of the composition is usually 1 to 50 in the case of a liquid.
% By weight, usually 0.3 to 25% by weight for powders, usually 1 to 90% by weight for wettable powders, and usually 0.3 to 25% by weight for granules.
It is.

These preparations can be used as they are or diluted to an appropriate concentration, and then applied to seeds or soil according to the purpose. In the case of hydroponics, it can be added directly to the hydroponic solution. The treatment time is not particularly limited, and the treatment may be performed at the time of sowing or transplanting, and there is no harm to the crop even when applied during the growth of the crop.

Hereinafter, the present invention will be described in more detail with reference to Examples and Test Examples, but the present invention is not limited thereto.

[0026]

EXAMPLES In the following description, parts and% indicate parts by weight and% by weight, respectively.

[0027]

Example 1 Compound A (50 parts), Protectol GDA
(Trade name, containing 50% of compound B-1; BASF Japan K.K.) 10 parts, Gohsenol GL-05S (brand name, Nippon Synthetic Chemical Industry K.K.) 2 parts, and Carplex # 80-S After mixing 38 parts (trade name, manufactured by Shionogi & Co., Ltd.), the mixture was pulverized with a hammer mill to obtain a wettable powder of the present invention.

[0028]

Example 2 50 parts of compound A, 25 parts of Proxel GXL (trade name, containing 20% of compound B-5, manufactured by ICI Japan KK), 2 parts of gohsenol GL-05S, and 2 parts of carplex # After mixing 23 parts of 80-S, the mixture was pulverized with a hammer mill to obtain a wettable powder of the present invention.

[0029]

Example 3 Compound A (4 parts), Protectol GDA4
Department, Carplex # 80 (trade name, Shionogi & Co., Ltd.)
4 g) and 88 parts of Geeklite NG (trade name, manufactured by Geeklite Co., Ltd.) were mixed and pulverized with a hammer mill to obtain a powder of the present invention.

[0030]

Example 4 Compound A (4 parts), Protectol DMT
(Trade name, containing 100% of compound B-2, manufactured by BASF Japan K.K.) 0.5 part and Sigleite NG 95.5
The resulting mixture was pulverized with a hammer mill to obtain the powder of the present invention.

[0031]

Example 5 Compound A (4 parts), Protectol GL40
After mixing 5 parts (trade name, containing 40% of compound B-3, manufactured by BASF Japan Ltd.), 5 parts of Carplex # 80 and 86 parts of Sigleite NG, the mixture was pulverized by a hammer mill and then mixed with a hammer mill. A powder was obtained.

[0032]

Example 6 Compound A (4 parts), Protectol KLC8
0 (trade name, containing 80% of compound B-4, manufactured by BASF Japan K.K.), 2.5 parts of carplex # 80.
After mixing 5 parts and 91 parts of Ziglite NG, the mixture was pulverized with a hammer mill to obtain a powder of the present invention.

[0033]

Example 7 4 parts of compound A, Proxel GLX10
Parts, 10 parts of carplex # 80 and Siglelite N
After mixing 76 parts of G, the mixture was pulverized with a hammer mill to obtain a powder of the present invention.

[0034]

Example 8 4 parts of Compound A, 2 parts of Compound B-6 and 94 parts of Siglyte NG were mixed and then pulverized with a hammer mill to obtain a powder of the present invention.

[0035]

Example 9 4 parts of the compound A, 2 parts of the compound B-7 and 94 parts of Sigleite NG were mixed and then pulverized with a hammer mill to obtain a powder of the present invention.

[0036]

Example 10 4 parts of Compound A, 2 parts of Compound B-8 and 94 parts of Ziglite NG were mixed and pulverized by a hammer mill to obtain a powder of the present invention.

[0037]

Example 11 4 parts of Compound A, 2 parts of Platings P (trade name, containing 99% of propyl ester of Compound B-9, manufactured by Ueno Pharmaceutical Co., Ltd.) and 94 parts of Sigleite NG were mixed, and then mixed with a hammer mill. This was pulverized to obtain the powder of the present invention.

[0038]

Example 12 10 parts of Compound A, Protectol GD
A solution of the present invention was obtained by mixing and dissolving 20 parts of A and 70 parts of N-methylpyrrolidone.

[0039]

Example 13 10 parts of compound A, 50 parts of Proxel GLX and Solfit (trade name, manufactured by Kuraray Co., Ltd.) 4
0 parts were mixed and dissolved to obtain a liquid preparation of the present invention.

[0040]

Example 14 27.5 parts of Gohsenol GL-05S and 0.5 part of Neocol YSK (trade name, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) were mixed with 97.5 parts of Sigleite NG, and an appropriate amount of water was added thereto, followed by kneading. After combining, extruded with a pelletizer (screen hole diameter 0.9 mm), granulated, dried at 110 ° C.,
A granulated carrier sized to 0.3 to 1.7 mm was obtained.

Separately, 4 parts of Compound A, Protectol GD
After mixing and dissolving 2 parts of A and 7 parts of propylene glycol, the granules of the present invention were obtained by absorption in 86.5 parts of the granulated carrier.

[0042]

Example 15 Compound A (4 parts) and Proxel GXL (5 parts)
Parts, and 5 parts of N, N-dimethylformamide were mixed and dissolved, and then Kagarite No. 2 (trade name, Silver Sangyo) 86
To obtain the granules of the present invention.

[0043]

Example 16 Compound C (4 parts), Protectol GDA
Was mixed with 4 parts of Carplex # 80 and 88 parts of Sigleite NG, and the mixture was ground with a hammer mill to obtain a powder of the present invention.

[0044]

Example 17 10 parts of Compound A, Protectol GD
A solution of the present invention was obtained by mixing and dissolving 20 parts of A, 50 parts of Proxel GXL and 20 parts of Solfit.

[0045]

Example 18 Compound C (50 parts), Protectol GD
A, 10 parts of Gohsenol GL-05S (manufactured by Nippon Synthetic Chemical Industry Co., Ltd.) and 3 parts of Carplex # 80-S
After mixing 8 parts, the mixture was pulverized with a hammer mill to obtain a wettable powder of the present invention.

[0046]

EXAMPLE 19 50 parts of Compound C, 25 parts of Proxel GXL, 2 parts of Gohsenol GL-05S and 23 parts of Carplex # 80-S were mixed and pulverized by a hammer mill to obtain a wettable powder of the present invention. I got

[0047]

Example 20 4 parts of Compound A, Protectol TOE
2 parts of trade name (containing 100% of compound B-10, manufactured by BASF Japan K.K.) and 94 parts of Ziglite NG,
After mixing, the mixture was pulverized with a hammer mill to obtain the powder of the present invention.

[0048]

EXAMPLE 21 5.7 kg of water, 0.57 kg of calcium hydroxide and 1.4 kg of 3-hydroxy-5-methylisoxazole were added to a 10-liter glass kolben, dissolved by heating at 80 ° C., and filtered while hot. . The filtrate was cooled to 0 ° C., and the precipitated crystals were collected by filtration and dried at 55 ° C. for 2 hours to obtain 1.0 kg of white crude crystals. The crude crystals were recrystallized from water, and the obtained crystals were dried at 55 ° C. for 2 hours to obtain white crystals.

Melting point: 280 ° C. decomp. Elemental analysis value (as C ₈ H ₈ N ₂ O ₄ Ca.4H ₂ O) Calculated value (%) C: 31.17 H: 5.23 N: 9.09 Actual value (%) C: 31.09 H: 5.24 N: 9.07 IR spectrum ν _max ^KBr cm ^-1 : 3377 (s), 3220 (w), 165
0 (w), 1626 (s), 1510 (s), 1410 (s), 1255 (s), 1150 (s), 1025
(s), 900 (s).

NMR spectrum (D ₂ O) ppm: 2.11 (3H, d, J = 0.
8Hz), 5.36 (1H, q, J = 0.8Hz).

Analytical value of water by Karl Fischer method Water content (as C ₈ H ₈ N ₂ O ₄ Ca · 4H ₂ O) Calculated value (%) 23.37 Actual measured value (%) 23.62 The above results were obtained. The compound is 3-hydroxy-5
-Calcium salt dihydrate of methyl isoxazole (compound D).

[0052]

Example 22 5.2 parts of Compound D and Protectol G
After mixing 4 parts of DA, 4 parts of Carplex # 80 and 86.8 parts of Sigleite NG, the mixture was ground with a hammer mill to obtain a powder of the present invention.

[0053]

Example 23 Compound D (65 parts), Protectol GD
A, 10 parts of Gohsenol GL-05S, and 2 parts of Carplex # 80-S were mixed and pulverized with a hammer mill to obtain a wettable powder of the present invention.

[0054]

Example 24 Compound D (65 parts), Proxel GXL (25 parts), Gohsenol GL-05S (2 parts) and Carplex # 80-S (8 parts) were mixed, and the mixture was ground with a hammer mill to obtain a wettable powder of the present invention. I got

[0055]

Comparative Example 1 50 parts of Compound A, Gohsenol GL-0
A wettable powder was obtained in the same manner as in Examples 1 and 2 using 2 parts of 5S and 48 parts of Carplex 80-S.

[0056]

Comparative Example 2 10 parts of Protectitol GDA, 2 parts of Gohsenol GL-05S and Carplex # 80-S
, And a wettable powder was obtained in the same manner as in Example 1 by using 88 parts of.

[0057]

Comparative Example 3 25 parts of Proxel GXL, 2 parts of Gohsenol GL-05S and 7 parts of Carplex # 80-S
A wettable powder was obtained in the same manner as in Example 2 using 3 parts.

[0058]

Comparative Example 4 A powder was obtained in the same manner as in Example 3, except that 4 parts of the compound A and 96 parts of Sigleite NG were used.

[0059]

Comparative Example 5 A powder was obtained in the same manner as in Example 3, except that 4 parts of Protectitol GDA, 4 parts of Carplex # 80 and 92 parts of Ziglite NG were used.

[0060]

Comparative Example 6 A dust was obtained in the same manner as in Example 4, except that 0.5 parts of Protectitol DMT and 99.5 parts of Ziglite NG were used.

[0061]

Comparative Example 7 A dust was obtained in the same manner as in Example 5, except that 5 parts of Protectol GL40, 5 parts of Carplex # 80 and 90 parts of Ziglite NG were used.

[0062]

Comparative Example 8 A dust was obtained in the same manner as in Example 6, except that 2.5 parts of Protectol KLC80, 2.5 parts of Carplex # 80 and 95 parts of Ziglite NG were used.

[0063]

Comparative Example 9 A powder was obtained in the same manner as in Example 7, except that 10 parts of Proxel GXL, 10 parts of Carplex # 80 and 80 parts of Ziglite NG were used.

[0064]

Comparative Example 10 Compound B-6 (2 parts) and Siglelite N
A powder was obtained in the same manner as in Example 8 using 98 parts of G.

[0065]

Comparative Example 11 Compound B-7 (2 parts) and Siglelite N
A powder was obtained in the same manner as in Example 9 using 98 parts of G.

[0066]

Comparative Example 12 Compound B-8 (2 parts) and Siglelite N
A powder was obtained in the same manner as in Example 10 using 98 parts of G.

[0067]

[Comparative Example 13] 2 parts of plating P and Zeekrite N
A powder was obtained in the same manner as in Example 11 using 98 parts of G.

[0068]

Comparative Example 14 Compound A was 10 parts and Solfit was 9
A liquid preparation was obtained in the same manner as in Example 13 using 0 parts.

[0069]

Comparative Example 15 20 parts of protector GDA and N-
A liquid preparation was obtained in the same manner as in Example 12 using 80 parts of methylpyrrolidone.

[0070]

Comparative Example 16 A liquid preparation was obtained in the same manner as in Example 13 except that 50 parts of Proxel GXL and 50 parts of Solfit were used.

[0071]

Comparative Example 17 Granules were obtained in the same manner as in Example 15 using 4 parts of the compound A, 8 parts of N, N-dimethylformamide and 88 parts of Kagarite No. 2.

[0072]

Comparative Example 18 Granules were obtained in the same manner as in Example 14 using 2 parts of Protectol GDA, 7 parts of propylene glycol, and 91 parts of the granulated carrier obtained in Example 14.

[0073]

Comparative Example 19 Granules were obtained in the same manner as in Example 15 except that 5 parts of Proxel GXL, 5 parts of N, N-dimethylformamide and 90 parts of Kagarite No. 2 were used.

[0074]

Comparative Example 20 A powder was obtained in the same manner as in Example 16 except that 4 parts of the compound C and 96 parts of Sigleite NG were used.

[0075]

[Comparative Example 21] Compound C, 50 parts, Gohsenol GL-
A wettable powder was obtained in the same manner as in Examples 18 and 19 using 2 parts of 05S and 48 parts of Carplex 80-S.

[0076]

Comparative Example 22 A dust was obtained in the same manner as in Example 20, except that 2 parts of Protectol TOE and 98 parts of Ziglite NG were used.

[0077]

Comparative Example 23 5.2 parts of Compound D and Sigrite N
A powder was obtained in the same manner as in Example 22 using 94.8 parts of G.

[0078]

Comparative Example 24 Compound D (65 parts), Gohsenol GL-
A wettable powder was obtained in the same manner as in Examples 23 and 24 using 2 parts of 05S and 33 parts of Carplex 80-S.

[0079]

Industrial Applicability The composition of the present invention remarkably enhances the disease control effect and physiological activity of compound A or a salt thereof, and enhances the residual effect, so that the dosage can be reduced.

Hereinafter, the effects of the present invention will be described more specifically.

[0081]

[Test Example 1] [Rice seedling damping-off control test (wettable powder)] Pythium graminum was previously cultured with shaking in a potato decoction medium.
icola ) was crushed with a blender to form a mycelial suspension, which was mixed and inoculated into sterilized soil. 20 ×
It was packed in a small plastic nursery box of 20 cm and 3 cm depth. Rice seeds (variety: Koshihikari), which had been immersed and germinated in advance, were subjected to Examples 1, 2, 18, and 19 and Comparative Example 1,
Immediately after a predetermined amount of the wettable powder prepared in 2, 3, and 21 was dressed, 30 g of this seed was sown with dry paddy weight per box. The seedlings were raised in a glass room at 20 ° C. in the daytime and 15 ° C. in the nighttime, and the area where the seedling damping-off was infested was examined two weeks after sowing, or three weeks and five weeks after sowing. The growth suppression of rice seedlings was examined two weeks after sowing.

Tables 1 and 2 show the results of this test. The control effect of Compound A and Compound C lasts for about 2 to 3 weeks, but the disease starts to rapidly develop after 5 weeks, and becomes severe after 5 weeks. The compound A, the compound C, the compound B-1 or the compound B-5 alone has a very low control effect, but when the compound A or the compound C is compounded with the compound B-1 or the compound B-5, the onset does not occur even after 5 weeks. Not at all.
As described above, the residual effects of Compound A and Compound C were remarkably enhanced, and a surprising control effect was exhibited. In addition, in the composition of the present invention, no phytotoxicity such as growth inhibition of rice seedlings was observed at any treatment amount, and instead root growth was promoted and healthy seedlings were grown. When treated at a high concentration (1% of seed weight), Compound A showed strong phytotoxicity (budding inhibition, growth inhibition),
Compound C, its calcium salt, showed no phytotoxicity at the same concentration.

In the following table, the column of rice seedling growth suppression was based on the following criteria.

-: No growth inhibition is observed ±: Slight growth inhibition is observed +: About 2/3 of the height of normal seedlings ++: About 1/3 of the height of normal seedlings +++: Non-budding

[0085]

[Table 1] ──────────────────────────────────── test compound seedling blight disease area ( % ) Rice seedling number vs. seed active ingredient concentration (%) 2 weeks after sowing 5 weeks after sowing Growth inhibition ────────────────────────── ────────── (Compound A) (Compound B-1) 0.05 0.005 0 0-Example 1 0.1 0.01 0 0-0.2 0.02 0 0-0.4 0.04 0 0-─────── ───────────────────────────── (Compound A) (Compound B-5) 0.05 0.005 00-Example 2 0.1 0.01 0 0 − 0.2 0.02 0 0 − 0.4 0.04 0 0 − ──────────────────────────────────── (compound A) 0.05 15 90-Comparative Example 1 0.1 0 50-0.2 0 30-0.4 0 10-──────────────────────── ─────────── (Compound B-1) 0.005 50 100-Comparative Example 2 0.01 40 100-0.02 25 90-0.04 15 70-────────────── ────────────────────── (Compound B-5) 0.01 30 100-Comparative Example 3 0.02 20 80-0.04 10 60-───────対 照 Control area 50 100 − ──────────────── ────────────────────

[0086]

[Table 2] ──────────────────────────────────── test compound seedling blight disease area ( % ) Rice seedling number vs. seed active weight (%) 3 weeks after sowing 5 weeks after sowing Growth inhibition ────────────────────────── ────────── (Compound C) (Compound B-1) 0.25 0.025 00-Example 18 0.5 0.05 0 0-1.0 0.1 00- ──────────────────────── (Compound C) (Compound B-5) 0.25 0.025 00-Example 19 0.5 0.05 0 0-1.0 0.1 0 0-──────────────────────────────────── (Compound A) 0.25 15 80-Comparative Example 1 0.5 0 60 ± 1.0 (Undetermined due to non-budding) +++ ────────────────────────────── ───── (Compound B-1) 0.025 40 100 Comparative Example 2 0.05 30 80 − 0.1 20 70 − ───────────────────────── ─────────── (Compound B-5) Comparative Example 3 0.05 30 90-0.1 25 80-────────────────────── ────────────── (Compound C) 0.25 20 80 − Comparative Example 21 0.5 0 50 − 1.0 0 20 − ───────────────── ─────────────────── Control area 40 100 − ────────────────────────── ──────────

[0087]

[Test Example 2] [Rice seedling damping-off control test (dust)] Examples 3 to 11, 16, 20, and 22 were applied to the same soil contaminated with pathogenic bacteria as in Test Example 1.
After the powders prepared in Comparative Examples 4 to 13, 20, 22, and 23 were mixed with all layers, sowing, seedling raising, and investigation were performed in the same manner as in Test Example 1.

Table 3 shows the results of this test. Compound A,
Compound C or Compound D alone has poor residual activity, and any of the antimicrobial agents has an extremely low controlling activity, but by compounding Compound A, Compound C or Compound D with any of the antimicrobial agents, The control effect of Compound A, Compound C or Compound D, including the residual effect, was significantly enhanced. Except for the compound B-8, none of the compounding agents observed any phytotoxicity such as growth inhibition of rice seedlings, but rather promoted root growth and grew healthy seedlings.

[0089]

[Table 3] ──────────────────────────────────── test compound seedling blight disease area ( % ) Rice seedling Amount of active ingredient per box (mg) 2 weeks after sowing 5 weeks after sowing Growth inhibition
(Compound A) (Compound B-1) 5 0 0 −
20 1000-──────────────────────────────────── (Compound A) (Compound B-2 Example 4 10 5 10 30 − 20 10 0 0 − ──────────────────────────────────── (Compound A) (Compound B-3) Example 5 10 55 60 −20 1000 − − ───────── (Compound A) (Compound B-4) Example 6 10 50 70-20 10 0 10- ────────────────── (Compound A) (Compound B-5) Example 7 10 500-20 10 00- ─────────────────────────── (Compound A) (Compound B-6) Example 8 10 5 10 50 − 20 10 0 20 − ────── ────────────────────────────── (Compound A) (Compound B-7) Example 9 10 5 10 30 -20 10 0 30-──────────────────────────────────── (Compound A) (Compound B-8) Example 10 10 5 0 40 −20 10 0 30 + ──────────────────────────────────── (compound A) (Compound B-9) Example 11 10 5 10 40 −20 10 0 35 −───────────────────────────── ─────── (Compound C) (Compound B-1) Example 16 10 500-20 10 00- ──────────────── (Compound A) (Compound B-10) Example 20 10 5 0 15-20 10 00- ───────────────────────── (Compound D) (Compound B-1) Example 22 10 500-20 10 00- ────────────────────────────────── (Compound A) Comparative Example 4 10 10 80 −20 0 40 − ─────────────────────────────────── (Compound B-1) Comparative Example 5 5 40 100 -10 30 80-──────────────────────────────────── (Compound B-2) Comparative Example 6 5 40 100 −10 35 100 −──────────────────────────────────── (Compound B-3) Comparative Example 7 5 40 100 − 10 30 90 − ──────────────────────────────────── (Compound B-4) Comparative Example 8 5 50 90-10 40 90-──────────────────────────────────── (Compound B-5) Comparative Example 9 5 25 100 −10 10 80 −──────────────────────────────────── (Compound B-6 ) Comparative Example 10 5 50 100 −10 30 100 −──────────────────────────────────── (Compound B-7) Comparative Example 11 5 50 100 −10 50 90 −─────────────────────────────────── ─ (Compound B-8) Comparative Example 12 5 40 100 -10 20 90 + ──────────────────────────────── ──── (Compound B-9) Comparative Example 13 5 40 100 −10 30 80 − ──── ── (Compound C) Comparative Example 20 10 15 80-20 0 50- ─── (Compound B-10) Comparative Example 22 5 50 100 -10 30 90-────────────────────────────── ────── (Compound D) Comparative Example 23 10 18 85 − 20 5 65 − −対 照 Control area 50 100 − ────────────────────────────────────

[0090]

[Test Example 3] [Cucumber wilt disease control test (solution)] Cucumber wilt fungus ( Fusar ) previously obtained by shaking culture in a potato decoction medium
A suspension of small conidia of ium oxysporum f . sp . cucumerinum ) was mixed and inoculated into sterilized soil and filled into a plastic pot (2 liter volume). After cucumber (cultivar: Sagami Hanshiro, two-leaf seedling of true leaf) was planted three per pot, a predetermined amount of the liquid preparation prepared in Examples 12, 13 and 17 and Comparative Examples 14, 15 and 16 was watered. Dilute, 10 per pot
Irrigation was performed in 0 ml portions. Cultivation was carried out in a glass room as one group of five continuous plants, and the percentage of healthy seedlings was examined after 3 weeks and 5 weeks. The test results are shown in Table 4.

The soil disease controlling composition of the present invention completely suppressed the onset of cucumber vine disease.

[0092]

[Table 4] 番号 Test compound healthy seedling ratio (%) No. Active ingredient concentration in irrigation solution (ppm) After 3 weeks After 5 weeks Chemical injury ────────────────────────────────── ── (Compound A) (Compound B-1) 200 200 100 95 None Example 12 400 400 100 100 None 600 600 100 100 None ──────────────────── ──────────────── (Compound A) (Compound B-5) 200 200 100 90 None Example 13 400 400 100 100 None 600 600 100 100 None ────── ────────────────────────────── (Compound A) (B-1) (B-5) Example 17 200 200 200 100 100 None 400 400 400 100 100 None ─────────────────────────── ───────── (Compound A) 200 30 0 None Comparative Example 14 400 50 10 None 600 60 10 None ────────────────────── ────────────── (Compound B-1) 200 25 0 None Comparative Example 15 400 25 0 None 600 30 0 None ─────────────── ───────────────────── (Compound B-5) 200 20 0 None Comparative Example 16 400 20 0 None 600 30 0 None ────────対 照 Control section 20 0 − ───────────────── ───────────────────

[0093]

Test Example 4 [Sugar beet seedling blight control test (granule)] A cultured bacterial cell containing the spores of Aphanomyces cochlioides previously obtained by culturing on a cornmeal agar medium supplemented with cholesterol is blended. The mixture was inoculated into sterilized soil, and filled in a plastic pot having a size of 30 × 40 cm and a depth of 20 cm. Seeds of sugar beet (variety: Monomidori) were seeded at 60 seeds per pot.
5 and 17 and Comparative Examples 18 and 19 were sprayed on the soil surface. After cultivation in a glass room for 6 weeks as a three-unit system in one area, the percentage of healthy seedlings was investigated. Table 5 shows the results of this test.

The soil disease controlling composition of the present invention showed a remarkable effect on the establishment of the sugar beet seedling blight.

[0095]

[Table 5] 化合物 Test compounds Healthy seedling rate No. Effective per pot Ingredient amount (mg) (%) Injury ──────────────────────────────────── (Compound A) ( Compound B-1) 10 2.5 60 None Example 14 20 5 90 None 40 10 100 None ────────────────────────────── ────── (Compound A) (Compound B-5) 10 2.5 70 None Example 15 20 5 90 None 40 10 100 None ─────────────────── ───────────────── (Compound A) 10 30 None Comparative Example 17 20 50 None 40 60 None ───────────────── ─────────────────── (Compound B-1) 2.5 20 None Comparative Example 18 5 25 None 10 25 None ──────────────────────────────────── (Compound B-5) 2.5 15 None Comparative Example 19 5 20 None 10 20 None 対 照 Control section 20 − ────── ──────────────────────────────

[0096]

[Test Example 5] [Test for control of sugar beet seedling damping-off (wettable powder)] As in Test Example 3, soil contaminated with pathogenic bacteria was filled in a plastic pot.
Examples 18, 19, 23 and 24 and Comparative Examples 1, 2,
3, 21 and 24 wettable powders were applied to seeds of sugar beet (cultivar: Monomidori and Kitakai No. 51) together with 2% gum arabic solution. After 60 seeds of the sugar beet seeds were sown per pot and cultivated in a glass room for 6 weeks in three sections per section, the percentage of healthy seedlings was examined. The results of the test are shown in Table 6.

The soil disease controlling composition of the present invention exhibited a remarkable controlling effect on the establishment of sugar beet seedling wilt, and no phytotoxicity was observed. In addition, compound A caused phytotoxicity.

[0098]

Table 6: Test compound Monomidori North Sea No. 51 vs. seed weight Active ingredient amount (%) Healthy seedling rate (%) Chemical damage Healthy seedling rate (%) Chemical damage ────────────────────────────── ────── (Compound C) (Compound B-1) Example 18 1.0 0.1 85 None 90 None 1.5 0.15 90 None 95 None ─────────────────── ───────────────── (Compound C) (Compound B-5) Example 19 1.0 0.1 80 None 88 None 1.5 0.15 90 None 95 None ──────── ──────────────────────────── (Compound D) (Compound B-1) Example 23 1.0 0.1 90 None 93 None 1.5 0.15 93 None 95 None ───────────────────────────────── ─── (Compound D) (Compound B-5) Example 24 1.0 0.1 85 None 90 None 1.5 0.15 95 None 95 None ────────────────────── ────────────── (Compound A) Comparative Example 1 1.0 37 None 60 None 1.5 53 Growth delay 57 Growth delay ───────────────── ─────────────────── (Compound B-1) Comparative Example 2 0.18 None 10 None 0.15 10 None 14 None ──────────── ──────────────────────── (Compound B-5) Comparative Example 3 0.1 7 None 11 None 0.15 10 None 13 None ─────── ───────────────────────────── (Compound C) Comparative Example 21 1.0 47 None 70 None 1.5 60 None 80 None ──── ─────────────────────────── ──── (Compound D) Comparative Example 24 1.0 50 None 75 None 1.5 55 None 80 None ───────────────────────────── ─────── Control 5 − 8 − ────────────────────────────────────

[0099]

[Test Example 6] [Rice submerged direct sowing test] 50 cm x 40 cm, depth 10 c
The paddy soil was packed into a 5 m plastic container to a depth of 5 cm, and the paddy was removed. Rice seeds (variety: Koshihikari) which had been immersed and germinated in advance were dressed with a predetermined amount of the wettable powder of Examples 18 and 19 and Comparative Examples 1 to 3 and 21 and immediately deepened 120 grains per section. Seeds were sown in 2 cm soil. Keep the water depth at 3-5cm, daytime 20 ℃, nighttime 15
The plants were cultivated in a glass room at 3 ° C. for 3 weeks, and the number of seedlings and the degree of chemical damage were examined. The results of the test are shown in Table 7.

The seedling establishment rate was higher in the group treated with compound C alone than in the group without treatment, but the compound B-1 or compound B
The seedling establishment rate of the group containing -5 was remarkably high. Compound B
The seedling establishment rate in the group treated with -1 or Compound B-5 in Germany was almost the same as that in the group without treatment. In addition, no phytotoxicity was observed at any of the treatment amounts of the compounding agents.

[0101]

[Table 7] 化合物 Test compound Seedling establishment rate Chemical injury vs. seed weight Effective amount (%) (%) ──────────────────────────────────── (Compound C) ( Compound B-1) Example 18 0.5 0.05 95 None ──────────────────────────────────── (Compound C) (Compound B-5) Example 19 0.5 0.05 92 None ─────────────────────────────────── ─ (Compound A) Comparative Example 1 0.5 68 None ──────────────────────────────────── (Compound B -1) Comparative Example 2 0.05 58 None ──────────────────────────────────── (Compound B- 5) Comparative Example 3 0.05 60 None ──────────────────────────────────── (Compound C) Comparative Example 21 0.5 72 None 対 照 Control area 54 None ────── ──────────────────────────────

[0102]

[Test Example 7] [Algicidal test of hydroponic solution] Pond water was put into a glass chamber to generate algae. Put this solution in a 100 ml beaker,
Examples 12 and 13 and Comparative Examples 14 and 15 at predetermined concentrations
And 16 solutions were added. After keeping this in a glass room for one week, the degree of algae generation was investigated.

Table 8 shows the results of the test. The composition of the present invention showed a remarkable algicidal action.

In the table, the degree of algae generation was based on the following criteria.

-: No occurrence is observed.

±: Slight occurrence is observed.

+: Occurrence is recognized.

++: Significant occurrence is observed.

+++: As in the non-treated control, the occurrence is severe.

[0110]

[Table 8] ───────────────────────────── Test compounds Algal occurrence concentration Concentration (ppm) ────── (Compound A) (Compound B-1) Example 12 30 30 −100 100 −──────── (Compound A) (Compound B-5) Example 13 30 30 -100 100- (Compound A) (Compound B-1) (Compound B-5) Example 17 10 10 10 −30 30 30 − ───────────────────────── (Compound A) Comparative Example 14 30 + 100 ± ────────────── ─────────────── (Compound B-1) Comparative Example 15 30 ++ 100 ++ ────────────────── ─────────── (Compound B-5) Comparative Example 16 30 +++ 100 ++ ─────────────────────── ────── Control +++ ─────────────────────────────

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/08 A01N 43/08 G 43/80 101 43/80 101 102 102 43/88 101 43/88 101 59/20 59 / 20Z (72) Inventor Shigehiro Kato 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Inside Sankyo Co., Ltd. (72) Inventor Yasuhiko Kondo 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Inside Sankyo Co., Ltd. (72) Inventor Yukiyoshi Takanaga Shiga 1041, Yasu-cho, Yasu-cho, Yasu-gun, Japan (56) References JP-A-49-1728 (JP, A) JP-A-51-110032 (JP, A) JP-A-58-99404 (JP, A) JP-A-56-79605 (JP, A) JP-A-57-85301 (JP, A) JP-A-56-87506 (JP, A) JP-B-43-10877 (JP, B1) JP-B-46-5160 ( JP, B1) JP 48-38148 (JP, B1) (58) style The field (Int.Cl. ^6, DB name) C07D 261/12 A01N 43/80 REGISTRY (STN ) CA (STN)

Claims (4)

(57) [Claims] (1) 3-hydroxy-5-methyl isoxa
Sol calcium dihydrate. 2. A soil disease control composition comprising the calcium salt dihydrate of 3-hydroxy-5-methylisoxazole according to claim 1 and a microbial control agent. 3. An antimicrobial agent comprising: 1,5-pentanedial, 2,5-dimethoxytetrahydrofuran, glyoxal, benzalkonium chloride, 1,2-benzisothiazolin-3-one, cupric hydroxide, p -Chloro-m-
Xylenol, p-chloro-o-cresol, n-propyl p-hydroxybenzoate and tetrahydro-
3,5-dimethyl-2H-1,3,5-thiadiazine-
The soil disease controlling composition according to claim 2 , which is one or more compounds selected from 2-thione. 4. The soil disease controlling composition according to claim 2 , wherein the antimicrobial agent is one or two compounds selected from 1,5-pentanedial and 1,2-benzisothiazolin-3-one. .