JP3349566B2 - Agricultural and horticultural fungicide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel fungicidal composition comprising a known fungicidal carboxamide or its optical isomer and a known fungicidal compound.

[0002]

BACKGROUND OF THE INVENTION The bactericidal carboxamides and their optical isomers according to the present invention are known ones described in JP-A-61-15867, JP-A-62-201855 and JP-A-2-11550. is there. Similarly, fungicidal compounds are disclosed in JP-B-45-38080, JP-A-3-24.
No. 6,268, EP-A-468684, JP-A-4-15228, JP-A-63-23852, JP-A-2-131481 and the like.

[0003] In rice cultivation, mechanical transplantation is mainly performed mainly by a seedling transplanter. In addition to controlling crop diseases in paddy fields and Honda, it is desired to control crop diseases and reduce labor by applying a nursery box of chemicals. ing. In addition, reduction of the amount of pesticide used and the number of times of use are strongly desired from the viewpoint of safety and environmental protection, and the use of even lower amount of pesticide is being studied.
In particular, in rice cultivation, control of blast which is an important disease to be controlled, control of labor, and further improvement in safety are expected.

[0004]

SUMMARY OF THE INVENTION The object of the present invention is, as described above, to realize the desired control of disease in rice cultivation as well as the use of a much lower dose in rice cultivation.

[0005]

SUMMARY OF THE INVENTION The present invention provides a compound of the formula:

Embedded image In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms;
² represents a hydrogen atom or a methyl group, R ³ represents a hydrogen atom or a methyl group, Z represents a halogen atom, and the asymmetric carbon of * represents the absolute configuration of R. Carboxamides, 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide, methyl- ( E) -Methoxyimino [α-
(O-tolyloxy) -o-tolyl] acetate,
(E) -2-methoxyimino-N-methyl-2- (2-
Phenoxyphenyl) acetamide, methyl- (E) -2
-{2- [6- (2-cyanophenoxy) pyrimidine-
4-yloxy] phenyl} -3-methoxyacrylate, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-
A novel mixed composition comprising as an active ingredient at least one selected from the group consisting of thiazole-5-carboxanilide and 3-allyloxy-1,2-benzisothiazole-1,1-dioxide, It has been found to exhibit excellent bactericidal action.

The fungicidal compositions of the present invention surprisingly surprisingly survive the fungicidal carboxamides of the formula (I),
Compared with the case where each of the known bactericidal compounds is used alone, the mixing according to the present invention expresses a surprisingly synergistic synergistic effect, thereby eliciting a remarkable bactericidal effect at a lower dose. Becomes possible. In addition, the fungicide composition of the present invention exhibits an appropriate control effect especially on rice blast.

In the carboxamides of the fungicide composition of the present invention, preferably, R ¹ represents methyl, ethyl or isopropyl, R ² represents a hydrogen atom or methyl, and R ³ represents a hydrogen atom or methyl. And Z represents chloro.

Specific examples of the compound of the formula (I) include, for example, N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3t-methyl-
Mixture of diastereomers of 1r-cyclopropanecarboxamide, mixture of diastereomers of N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclopropanecarboxamide , N- (R)-[1- (4-chlorophenyl)-
Ethyl]-(1S) -2,2-dichloro-1-ethyl-
3t-methyl-1r-cyclopropanecarboxamide,
And N- (R)-[1- (4-chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1-isopropylcyclopropanecarboxamide.

In the active substance combinations according to the invention, the proportion by weight of active substance can be varied within a relatively wide range. In general, the above-mentioned known fungicidal compounds are used in an amount of about 0.0% per part by weight of the fungicidal carboxamides of the formula (I).
2 to about 50 parts by weight, preferably about 0.1 to about 10 parts by weight. The fungicidal composition of the present invention exhibits a strong fungicidal action and can in fact be used to control unwanted phytopathogenic bacteria.

[0010] The active compound combinations according to the invention are generally used as fungicides (Plasmodiophoromycetes),
Omycetes, Oxymycetes, Chitridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes (Ba)
sidiomycetes) and deuteromycetes (D
eutheromycetes), and can be used as a fungicidal (bacterial) agent as a Pseudomonadacea.
e), Rhizobiaceae, Enterobacteriaceae (Enterobacteriaceae)
eae), Corynebacterium (Corynebac)
teriaceae) and Streptomyces (Str)
It can be used for various plant diseases caused by E. mycobacterium. In particular, the active substance combinations according to the invention can be used for rice blast (Pyricularia or
yzae) shows an excellent control effect.

The active compound combination of the present invention exhibits good compatibility with plants at the concentration of the active compound necessary for controlling plant pathogens.
It enables chemical treatment of the above-ground parts of plants, chemical treatment of rootstocks and seeds, and soil treatment. Further, the combination of the compounds of the present invention has low toxicity to warm-blooded animals and can be used safely. The active compound combinations according to the invention can be in the form of a mixed composition of the bactericidal carboxamides and the known bactericidal compounds or in the form of a single individual preparation respectively for in situ mixing.
And such forms include solutions, wettable powders, emulsions, suspensions, powders, foams, pastes, granules, tablets, aerosols, active compound infiltration-natural and synthetic, microcapsules, seed coatings, Formulations equipped with a combustion device (for example, fumigation and fume cartridges, cans and coils as combustion devices), and ULV [cold mist (c
old mist), warm mist (warm mi)
st)].

These preparations can be manufactured by a known method. Such methods include, for example, the use of an active compound as a developing agent, ie, a liquid diluent; a liquefied gas diluent; a solid diluent or carrier, optionally a surfactant, ie, an emulsifier and / or dispersant and / or foam. It is performed by mixing with a forming agent. If water is used as the developing agent, for example, organic solvents can also be used as auxiliary solvents.

The liquid diluent or carrier generally includes aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride). , Methylene chloride, etc.), aliphatic hydrocarbons (eg, cyclohexane, etc., paraffins (eg, mineral oil fractions, etc.)), alcohols (eg, butanol, glycol and their ethers, esters, etc.), ketones (eg, , Acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvents (eg, dimethylformamide, dimethyl sulfoxide, etc.)
And water. The liquefied gas diluent or carrier is a gas at normal temperature and pressure, examples of which include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. . Examples of the solid diluent include soil natural minerals (eg, kaolin, clay, talc, chalk, quartz, attapull guide, montmorillonite or diatomaceous earth), and soil synthetic minerals (eg, highly dispersed silicic acid, alumina, silicate, etc.). be able to.

Solid carriers for granules include ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders, and organic materials (eg, , Cob and coconut, corn cob and tobacco stem). Examples of the emulsifier and / or foaming agent include nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (for example, alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, aryl sulfone). Acid salt)] and albumin hydrolysis products. Dispersants include, for example, lignin sulfite waste liquors and methylcellulose.

Fixatives can also be used in the formulation (powder, granules, emulsions), such as carboxymethylcellulose and natural and synthetic polymers (eg,
Gum arabic, polyvinyl alcohol and polyvinyl acetate). Coloring agents can also be used, such as inorganic pigments (eg, iron oxide, titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron, Manganese, boron,
Mention may be made of trace elements such as copper, cobalt, molybdenum, zinc salts thereof. The formulation generally comprises
0.1 to 95% by weight of the active ingredient, preferably 0.5
９０90% by weight.

The active compounds according to the invention can be used in the abovementioned preparations or in various use forms in the form of other known active compounds, such as insecticides, acaricides, nematocides, herbicides, bird repellents, growth regulators, fertilizers and / or fertilizers. Alternatively, a soil conditioner can also be allowed to coexist. When using the active compounds according to the invention,
Use directly as it is, or use it in the form of preparations such as liquid preparations, emulsions, suspensions, powders, pastes and granules (including tablets) for spraying, or use forms prepared by further dilution Can be used. The active compound is then prepared in the customary manner, for example by watering,
Immersion, spraying, atomizing,
It can be used in misting, fumigation, irrigation, suspension formation, application, dusting, dusting, dusting, wet coating, wet coating, pasty coating or feather coating.

In treating each part of the plant, the concentration of active compound in the actual use form can be varied within a substantial range. And generally 0.0001 ~
It is 1% by weight, preferably 0.001 to 0.5% by weight. For seed treatment, the active compound is applied per kg of seed,
0.001 to 50 g, preferably 0.01 to 10 g generally can be used. In soil treatment, 0.00001 to 0.1% by weight, particularly 0.1% by weight, based on the point of action.
Active compounds in a concentration of from 0001 to 0.02% by weight can generally be used. Next, the content of the present invention will be specifically described with reference to examples, but the present invention should not be limited to these.

[0018]

【Example】

Biological test: Test compound (I) -a: N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-ethyl-3t
A mixture of diastereomers of -methyl-1r-cyclopropanecarboxamide, (I) -b: N- (R)-[1- (4-chlorophenyl) -ethyl] -2,2-dichloro-1-isopropylcyclo A mixture of diastereomers of propanecarboxamide, (I) -c: N- (R)-[1- (4-chlorophenyl) -ethyl]-(1S) -2,2-dichloro-1-ethyl-3t- Methyl-1r-cyclopropanecarboxamide,

A: 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide B: methyl -(E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate C: (E) -2-methoxyimino-N-methyl-2-
(2-phenoxyphenyl) acetamide D: methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl}
-3-methoxyacrylate E: 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3
-Thiazole-5-carboxanilide F: 3-allyloxy-1,2-benzisothiazole-1,1-dioxide

Test Example 1 Application of nursery box to rice blast Preparation of test compound Each active compound: 25 to 50 parts by weight Carrier: mixture of diatomaceous earth and kaolin (1: 5) 45 to 45
70 parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkylphenyl ether The above-mentioned amounts of the active compound, the carrier and the emulsifier are pulverized and mixed to prepare a wettable powder, and a predetermined amount thereof is diluted with water and mixed.

Test Method Alluvial soil was packed in a 100 cm ² plastic vagna pot to make it flooded. After scratching, remove water on the surface and remove
After standing for a day, a hole having a diameter of 2 cm and a depth of 3 cm was made in the center of the soil surface, and a predetermined amount of the water diluent prepared as described above was dropped on the bottom of the hole for treatment. Rice seedlings of the two-leaf stage and three stalks of varieties Cusabue were inserted into the holes, covered with dry soil, and transplanted. Then, after raising the seedlings in a greenhouse at a temperature of 20 to 33 ° C. for 30 days, the rice blast spores were spray-inoculated by a conventional method.
Seven days after inoculation, the degree of illness per pot was classified and evaluated according to the following criteria, and the control value (%) was determined. He also investigated phytotoxicity.

Degree of morbidity Lesion area percentage (%) 0 0.52 or less 13 to 5 26 to 10 3 11 to 20 4 21 to 40 5 41 or more

(Equation 1) This test is the result of 3 pots per section. Table 1 shows the results.

[0023]

[Table 1]

[0024]

[Table 2]

[Table note]

(Equation 2) Active ingredient amount (g / box) is 100cm ² plastic wag
The application rate per napot is set in a plastic nursery box (30 ×
60 × 3cm length × width × height)
Indicates a value.

Test Example 2 Test of foliar spraying efficacy against rice blast Test method Paddy rice (variety: Kusabue) was grown in a clay pot having a diameter of 12 cm, and the test compound prepared as in Test Example 1 in the 3-4 leaf stage Of the predetermined concentration was sprayed at 50 ml per three pots. Two days later, a suspension of artificially cultured rice blast spores was spray-inoculated (twice) and infected in a humidity chamber at 25 ° C. and 100% relative humidity. Seven days after inoculation, the degree of illness per pot was categorized and evaluated according to the following criteria, and the control value (%) was determined. At the same time, phytotoxicity was investigated.

Degree of morbidity Lesion area percentage (%) 0 0.52 or less 13 to 5 26 to 10 3 11 to 20 4 21 to 40 5 41 or more

(Equation 3) This test is the result of 3 pots per section. Table 2 shows the results.

[0027]

[Table 3]

[0028]

[Table 4]

Test Example 3 Water surface application efficacy test against rice blast Test method Paddy rice (variety: Kusabue) was placed in a white porcelain pot having a diameter of 12 cm.
The plant was planted and submerged, and at the initial stage of the splitting, using a pipette, a drug solution of a predetermined concentration prepared in the same manner as in Test Example 1 so that the drug solution was not directly applied to the aerial part of the rice body, so that the indicated drug amount was obtained.
Water was irrigated. Five days later, a suspension of rice blast spores was spray-inoculated by a conventional method, and the temperature was 23 ° C to 25 ° C.
They were kept in the inoculation room at a relative humidity of 100% for 24 hours. Thereafter, the mixture was transferred to a glass greenhouse at a temperature of 20 to 28 ° C., and 7 days after inoculation, the same investigation as in Example 1 was performed to determine the control value (%). At the same time, phytotoxicity was investigated. Table 3 shows the results.

[0030]

[Table 5]

[0031]

[Table 6]

[0032]

[Table 7]

Test Example 4 Water surface application efficacy test against rice sheath blight Test method Paddy rice (variety: Kusabue) was placed in a white porcelain pot having a diameter of 12 cm.
The plant was planted, submerged and cultivated, and in the booting stage, using a pipette, a drug solution of a predetermined concentration prepared in the same manner as in Test Example 1 so that the drug solution would not be directly applied to the aerial part of the rice body, so that the indicated drug amount was obtained. Water was irrigated. Ten days after that, the cultured cells of the rice sheath blight fungus were inoculated in a conventional manner and kept in an inoculation box at a temperature of 25 ° C. to 30 ° C. and a relative humidity of about 90% for 10 days to progress the disease. In the investigation, the degree of damage was expressed according to the following criteria based on the lesion extension from the inoculation site of the strain.

[0034]

(Equation 4) N: Total number of stems investigated n ₁ : Number of stems affected to first leaf leaf sheath (from below) n ₂ : Number of stems affected to second leaf leaf sheath (from below) n ₃ : Third leaf leaf sheath (lower) The number of stalks affected to above) The control value was calculated from the degree of damage by the following formula.

(Equation 5) Table 4 shows the results.

[0035]

[Table 8]

[0036]

[Table 9]

[0037]

[Table 10]

[0038]

The fungicidal composition of the present invention, as shown in the above examples, exhibits an excellent control effect against diseases and has a higher effect on the composite composition than the concentration when used alone. At lower concentrations, they show an effective control effect with synergistic synergistic effects.

Continuation of the front page (51) Int.Cl. ⁷ Identification symbol FI A01N 43/80 103 A01N 53/00 510 (56) References JP-A-62-161705 (JP, A) JP-A-3-31202 (JP, A) JP-A-2-11550 (JP, A) JP-A-63-54350 (JP, A) JP-A-5-112412 (JP, A) JP-A-5-59396 (JP, A) JP-A-6 -256118 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A01N 53/12 A01N 37/50 A01N 43/54 A01N 43/56 A01N 43/78 A01N 43/80 103 CA ( STN) REGISTRY (STN)

Claims (2)

(57) [Claims] (1) Formula (1) In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms;
² represents a hydrogen atom or a methyl group, R ³ represents a hydrogen atom or a methyl group, Z represents a halogen atom, and the asymmetric carbon of * represents the absolute configuration of R. Carboxamides, 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide, methyl-
(E) -methoxyimino [α- (o-tolyloxy)-
o-tolyl] acetate, (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide, methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidine -4-yloxy] phenyl}
-3-methoxy acrylate and 2 'is selected from 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5 Karubokisaaniri de by Ri comprising compounds An agricultural and horticultural fungicide composition comprising at least one active ingredient. 2. The bactericidal carboxamide is N- (R)-[1- (4-chlorophenyl) -ethyl].
-2,2-dichloro-1-ethyl-3t-methyl-1r
A mixture of diastereomers of -cyclopropanecarboxamide, N- (R)-[1- (4-chlorophenyl) -ethyl]
A mixture of diastereomers of -2,2-dichloro-1-isopropylcyclopropanecarboxamide, N- (R)-[1- (4-chlorophenyl) -ethyl]
-(1S) -2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide, and N-
(R)-[1- (4-chlorophenyl) -ethyl]-
The fungicide composition for agricultural and horticultural use according to claim 1, which is one kind selected from (1S) -2,2-dichloro-1-isopropylcyclopropanecarboxamide.