JP2001187705A - Plant disease control agent composition and method for controlling plant disease - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a plant disease control agent composition having a high activity. SOLUTION: This plant disease control agent composition is characterized by containing at least one compound selected from N-(3,5-dichlorophenyl)-1,2- dimethylcyclopropane-1,2-dicarboximide, 3-(3,5-dichlorophenyl)-N-(1- methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide, and 3-(3,5-dichlorophenyl)-5- methyl-5-vinyl-1,3-oxazolidine-2,4-dione, and a pyrazolinone derivative specified in the specification as active ingredients.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a composition for controlling plant diseases and a method for controlling plant diseases.

[0002]

2. Description of the Related Art Various plant disease control agents have been developed to control plant diseases. However, more active plant disease control agents have always been required.

An object of the present invention is to provide a composition for controlling plant diseases having high activity and a method for effectively controlling plant diseases.

[0004]

Under such circumstances, the present inventors have studied the control of plant diseases, and as a result, by using certain pyrazolinone derivatives in combination with a specific imide compound, a high synergistic effect in controlling plant diseases can be obtained. The inventors have found that they can be obtained, and have reached the present invention.

That is, the present invention relates to N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,
2-dicarboximide (hereinafter referred to as compound II), 3-
(3,5-dichlorophenyl) -N- (1-methylethyl) -2,4-dioxo-1-imidazolidincarboxamide (hereinafter referred to as compound III) and 3- (3,5-dichlorophenyl) -5-methyl -5-vinyl-1,3-
At least one imide compound selected from oxazolidine-2,4-dione (hereinafter, referred to as compound IV);

Embedded image [Wherein R ₁ represents a halogen atom or a methyl group optionally substituted with a halogen atom, R ₂ represents a hydrogen atom, a halogen atom or a methyl group optionally substituted with a halogen atom, and R ₃ represents isopropyl A secondary butyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a tert-butyl group or a 1,1-dimethylpropyl group, R ₄ represents an oxygen atom or a sulfur atom, and R ₅ represents C1
-C5 alkyl group, C2-C5 alkynyl group, C3-C
5 represents an alkenyl group. A plant disease controlling agent composition (hereinafter, referred to as the present invention composition) containing a pyrazolinone derivative (hereinafter, referred to as compound I) represented by the formula (I) below, and a plant, a plant cultivation area or a plant seed. ,Compound
It is intended to provide a method for controlling plant diseases (hereinafter, referred to as the method of the present invention), which comprises applying at least one imide compound selected from II, III, and IV and compound I.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION First, compound I will be described. In R ₁ and R ₂ of compound I, examples of the halogen atom include a fluorine atom and a chlorine atom. Examples of the methyl group which may be substituted with a halogen atom include a methyl group, a trifluoromethyl group and a trichloromethyl group. In R _5, as the C1~C5 alkyl group, a methyl group, an ethyl group, a propyl group, a butyl group, and examples of the C2~C5 alkynyl group, 2-propynyl, 2-butynyl, 3-butynyl group And the C3-C5 alkenyl group includes a 2-propenyl group, a 2-butenyl group and a 3-butenyl group.

[0007] Compound I can exist as a tautomer represented by the following formula 3, for example, but in the present specification, these and other tautomers are represented as compound I.

Embedded image Compound I may have a stereoisomer based on a double bond and / or an asymmetric carbon.
Include these stereoisomers and mixtures of two or more thereof. Table 1 shows specific examples of Compound I together with the compound numbers.
(Shown in the definition of each substituent of the compound represented by the general formula 2).

[Table 1]

[Table 2]: In Tables 1 and 2, Me represents a methyl group and Et represents ethyl.
Group secBu is a sec-butyl group, isoPr
Represents an isopropyl group. (+) In the compound number
The compound with the notation has a positive optical rotation.
(Optical solvent: methanol)
You. If there is a notation (-), the compound is minus
Optically active substance having optical rotation of (solvent: methanol)
Indicates that

Production Example 1 (1) Bis (trichloromethyl) carbonate 0.98
g (3.29 mmol) in 1,4-dioxane 10 ml
And pyridine 0.79 g (10.0 m
mol) was added dropwise. After stirring at room temperature for 30 minutes, 1.35 g of 2-propene-1-thiol (55% purity) (10.
0 mmol) was added dropwise, and the mixture was further stirred at room temperature for 30 minutes, and then the reaction solution was filtered to obtain a filtrate (hereinafter, this filtrate is referred to as "filtrate A"). (2) To 107 g (313 mmol) of 3-amino-2-tert-butyl-1-isopropyl-4- (2,6-dichlorophenyl) -3-pyrazolin-5-one was added 300 ml of 3N hydrochloric acid and 100 ml of ethanol. The mixture was stirred under reflux conditions for 4 hours. Thereafter, ethanol was distilled off under reduced pressure, the aqueous layer was neutralized with a dilute aqueous sodium hydroxide solution, and the precipitated solid was collected by filtration. The solid was washed with water and ethyl acetate and dried under reduced pressure to give 88.4 g of the compound of formula (309
mol).

Embedded image In addition, 3-amino-2-tert-butyl-1-isopropyl-4- (2,6-dichlorophenyl) -3-pyrazolin-5-one was produced according to the method described in JP-A-8-208621. You can do it. (3) 1.41 g of the compound of formula 4 obtained in (2) (4.
93 mmol) and 0.42 g of lithium hydroxide monohydrate
(10.0 mmol) and refluxed for 30 minutes while adding 20 ml of toluene and removing water by an azeotropic dehydration operation. The toluene was distilled off under reduced pressure, and 10 ml of 1,4-dioxane was added. Under reflux, the entire amount of "filtrate A" obtained in (1) was added dropwise, and the mixture was further stirred for 10 minutes under reflux conditions, and 1,4-dioxane was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with water, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 0.14 g of compound I-o.
(0.36 mmol) was obtained. Melting point 170.8 ° C
The compounds described in Tables 1 and 2 other than Io can also be obtained by a method according to the above-mentioned production method.

N- (3,5-dichlorophenyl) -1,
2-dimethylcyclopropane-1,2-dicarboximide is a general name procymidone, and 3- (3,5-dichlorophenyl) -N- (1-methylethyl) -2,4-dioxo-1-imidazolidincarboxamide is a general name The name iprodione and 3- (3,5-dichlorophenyl) -5
-Methyl-5-vinyl-1,3-oxazolidine-2,
4-diones are compounds known under the generic name vinclozolin, and are described in the Farm Chemicals Handbook 99
Fiscal version page C-318 (procimidon), C-22
It is described on page 4 (iplodione) and page C-407 (vinclozolin), respectively, and is a commercially available compound.

[0010] Plant diseases that can be controlled by the present invention include, for example, the following diseases. Usually, in the method of the present invention, the composition of the present invention is used. Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia)
solani), powdery mildew of wheat (Erysiphe graminis),
Fusarium head blight (Gibberella zeae), rust (Puccinia strii)
formis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronectriella nivalis), naked smut (Ustilago tritici, U. nuda), black smut (Ti.
lletia caries), eye spot disease (Pseudocercosporella herpot)
richoides), scald (Rhynchosporiumsecalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodo)
rum), citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium di
gitatum, P. italicum) and Monilia disease of apples (Sclero
tinia mali), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), spot leaf spot (Alternaria
mali), scab (Venturia inaequalis), pear scab (Venturia nashicola, V. pirina), black spot (Alternar
ia kikuchiana), scab (Gymnosporangium haraeanu)
m), peach scab (Sclerotinia cinerea), scab (Cl
adosporium carpophilum), Phomopsis rot (Phom
opsis sp.), black currant on grape (Elsinoe ampelina),
Late rot (Glomerella cingulata), powdery mildew (Uncinu)
la necator), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Pl
asmopara viticola), oyster anthracnose (Gloeosporium kak)
i), deciduous disease (Cercospora kaki, Mycosphaerella nawa
e), cucumber anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Myco
sphaerella melonis), vine disease (Fusarium oxysporu)
m), downy mildew (Pseudoperonospora cubensis), plague (P
hytophthora sp.), seedling blight (Pythium sp.), tomato ring spot (Alternaria solani), leaf mold (Cladospori)
um fulvum), plague (Phytophthora infestans), eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe c)
ichoracearum), black spot of cruciferous vegetables (Alternaria
japonica), white spot (Cercosporella brassicae), green onion rust (Puccinia allii), soybean purpura (Cercos
pora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), kidney anthracnose (Colletotrichum lindemthianum), peanut black rot (Cercospora personata), brown spot (Cercospor)
a arachidicola), pea powdery mildew (Erysiphepis)
i), potato summer blight (Alternaria solani), blight (Phytophthora infestans), strawberry powdery mildew (Sp
haerotheca humuli), tea net blast (Exobasidium re
ticulatum), scab (Elsinoe leucospila), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe)
cichoracearum), Anthracnose (Colletotrichum tabacum)
, Downy mildew (Peronospora tabacina), plague (Phytophth
ora nicotianae), brown spot of sugar beet (Cercospora beti)
cola), rose scab (Diplocarponrosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum spot on chrysanthemum (Septoria c
hrysanthemi-indici), white rust (Puccinia horiana)
The composition of the present invention can also be used against bacteria (disease) resistant to imide compounds such as iprodione, procymidone, vinclozolin, etc. Shows excellent control effect.

In the composition of the present invention, the ratio of the compound I to at least one imide compound selected from the compounds II, III and IV is usually 0.5 to 8: 1 by weight, preferably 1-2: It is one.

When the composition of the present invention is used in the method of the present invention, at least one imide compound selected from compounds II, III and IV and compound I without any other component are added.
(Hereinafter, referred to as the present active ingredient) may be used as it is, but usually, the present active ingredient is mixed with a solid carrier, a liquid carrier, a gas carrier, a surfactant and the like, and if necessary, a fixing agent, a dispersant, and a stabilizing agent. Formulation auxiliaries such as preparations are added to make wettable powders, flowables, granules, dry flowables, emulsions, aqueous solutions, oils, smokes, aerosols, microcapsules and the like. In these preparations, the active ingredient is usually 0.1 to 99% by weight, preferably 0.2 to 9% by weight.
0% is contained.

Examples of the solid carrier used in the preparation include minerals such as kaolin clay, attapargite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, and corn cob powder. , Natural organic substances such as walnut shell powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, fine powders or granular substances of synthetic inorganic substances such as synthetic silicon oxide hydroxide, and the like. Examples of the liquid carrier include xylene, Aromatic hydrocarbons such as alkylbenzene and methylnaphthalene, isopropanol, ethylene glycol,
Alcohols such as propylene glycol and cellosolve,
Examples include ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum aliphatic hydrocarbons, esters, dimethyl sulfoxide, acetonitrile, and water. Examples of the surfactant include alkyl sulfate, alkyl (aryl) sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkyl aryl ether phosphate, lignin sulfonate, and naphthalene sulfonate formalin condensation. Surfactants, and nonionic surfactants such as polyoxyethylene alkylaryl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, and sorbitan fatty acid ester. Examples of the gas carrier include LPG such as butane and propane, and nitrogen and carbon dioxide. Examples of the formulation auxiliary include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid or a salt thereof, polysaccharides such as CMC (carboxymethylcellulose) and xanthan gum, aluminum magnesium silicate, and alumina sol. Inorganic substances, preservatives, coloring agents, P
Stabilizers such as AP (acidic isopropyl phosphate) and BHT are exemplified.

Also, for example, each of the present active ingredients is separately formulated by the above-mentioned method, and if necessary, each is further diluted with water, and then the separately prepared preparation or the separately prepared diluent is mixed. By doing so, the composition of the present invention can also be prepared.

The method of applying the composition of the present invention is not particularly limited as long as the composition of the present invention can be applied substantially. Examples thereof include treatment of plants such as foliage application and soil treatment. And the like, and treatment of seeds such as seed disinfection.

In the method of the present invention, the application rate of the present active ingredient varies depending on the type of the target plant (crop etc.), the type of the target disease, the degree of occurrence of the disease, the formulation, the application method, the application time, the weather conditions, and the like. But usually 0.1-per arc
50 g, preferably 1 to 10 g, and the ratio of compound I to at least one imide compound selected from compounds II, III and IV in the present active ingredient is usually 0.5 to 8: 1 by weight. , Preferably 1-2: 1. emulsion,
The wettable powder, the suspending agent and the like are usually applied after being diluted with water, and the active ingredient concentration is usually 0.0005 to 2%, preferably 0.1 to 0.5%.
005% to 1%, and powders, granules and the like are usually applied without dilution. In the treatment of seed, the present active ingredient is usually 0.001 to 100 per 1 kg of seed.
g, preferably in the range of 0.01 to 50 g.

[0017]

EXAMPLES The present invention will be described in more detail with reference to Formulation Examples and Test Examples, but the present invention is not limited to the following Examples. In the following examples, parts are by weight unless otherwise specified. Compound I is indicated by the compound number shown in Tables 1 and 2.

Formulation Example 1 Compounds (Ia), (Ib), (Ic), (I-
d), (Ie), (If), (Ig), (I-
h), (Ii), (Ij), (Ik), (I-
l), (Im), (In), (Io) or (I
Each emulsion is obtained by thoroughly mixing 2.5 parts of -p), 2.5 parts of compound II, 14 parts of polyoxyethylenestyrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 2 Compounds (Ia), (Ib), (Ic) and (I-
d), (Ie), (If), (Ig), (I-
h), (Ii), (Ij), (Ik), (I-
l), (Im), (In), (Io) or (I
5 parts of p), 5 parts of compound II, 35 parts of a mixture of white carbon and ammonium polyoxyethylene alkyl ether sulfate (weight ratio 1: 1) and 55 parts of water.
Parts are mixed and finely pulverized by a wet pulverization method to obtain each flowable preparation.

Formulation Example 3 Compounds (Ia), (Ib), (Ic) and (I-
d), (Ie), (If), (Ig), (I-
h), (Ii), (Ij), (Ik), (I-
l), (Im), (In), (Io) or (I
-P), 5 parts of compound II, 10 parts of compound II, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol were mixed, finely pulverized by a wet pulverization method, and 0.5 g of xanthan gum was added thereto. And 45 parts of an aqueous solution containing 0.1 part of aluminum magnesium silicate, and 10 parts of propylene glycol are further added and stirred and mixed to obtain each flowable preparation.

Formulation Example 4 Compounds (Ia), (Ib), (Ic) and (I-
d), (Ie), (If), (Ig), (I-
h), (Ii), (Ij), (Ik), (I-
l), (Im), (In), (Io) or (I
-P), 1 part of compound II, 2.5 parts of synthetic hydrous silicon oxide, 1 part of synthetic hydrated calcium hydroxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 63.5 parts of kaolin kure, well mixed and added with water. After kneading, each granule is obtained by granulation and drying.

Formulation Example 5 Compounds (Ia), (Ib), (Ic) and (I-
d), (Ie), (If), (Ig), (I-
h), (Ii), (Ij), (Ik), (I-
l), (Im), (In), (Io) or (I
-P) 12.5 parts, compound II 37.5 parts, calcium lignin sulfonate 3 parts, sodium lauryl sulfate 2
Parts and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder.

Formulation Example 6 Compounds (Ia), (Ib), (Ic), (I-
d), (Ie), (If), (Ig), (I-
h), (Ii), (Ij), (Ik), (I-
l), (Im), (In), (Io) or (I
-P), 1 part of Compound II, 2 parts of Compound II, 85 parts of Kaolin Kure and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder.

Test Example 1 A plastic pot was filled with sandy loam, cucumber (Sagami Hanjiro) was sowed, and grown in a greenhouse for 12 days. Compound (I
-J) wettable powder and procymidone wettable powder were each diluted with water and then mixed with a tank to give a compound (I-
A tank mix solution containing j) and procymidone as active ingredients was prepared. The tank mix solution was sprayed on foliage so as to sufficiently adhere to the leaf surface of the cucumber. After spraying, the plants were air-dried, and a PDA medium containing spores of cucumber gray mold fungus resistant to procymidone was placed on the cucumber leaves. 10 after inoculation
After 6 days under high temperature and high temperature, the control effect was investigated. For comparison, a compound (I-j) solution and a procymidone solution were prepared by diluting each of the above wettable powders with water to a predetermined concentration, and the same control test was performed. In addition, the disease severity in the case of no treatment was also investigated for calculating the control value. The following evaluation indices were used during the survey. The disease severity was calculated from Formula 1, and the control value (%) was calculated using Formula 2 based on the disease severity. The results are shown in Table 3.

Test Example 2-4 Compounds (Ii) and (In) in place of compound (Ij)
Or the same experiment was performed except that (Io) was used.
The results are shown in Table 3.

Evaluation index 0: Lesion diameter 0 mm, 1: 1-5 mm, 2: 5-10 m
m, 3: 10-15 mm, 4: 15-20 mm, 5:>
20mm

[Formula 1] Disease incidence = Σ (evaluation index of survey leaf) x 100 /
(5 x number of leaves surveyed)

Formula 2: Control value (%) = 100 × (A−B) / A A: Degree of disease on plants in untreated area B: Degree of disease on plants in treated area In general, given two types of active ingredient compounds The control effect expected when mixed and treated, that is, the so-called expected value of the control value, can be obtained by Colby's calculation formula of the following formula 3.

Formula 3: E = X + Y- (XY) / 100 X: Control value (%) when active compound A is treated with Mppm Y: Control value (%) when active compound B is treated with Nppm : Active ingredient compound A in Mppm, active ingredient compound B
Value (%) (expected control value) expected when N is treated with Nppm

[Table 3]

[0027]

According to the present invention, it is possible to effectively control plant diseases.

Claims (2)

[Claims] (1) N- (3,5-dichlorophenyl) -1,
2-dimethylcyclopropane-1,2-dicarboximide, 3- (3,5-dichlorophenyl) -N- (1-
At least one selected from methylethyl) -2,4-dioxo-1-imidazolidinecarboxamide and 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione And an imide compound of the general formula 1 [Wherein R ₁ represents a halogen atom or a methyl group optionally substituted with a halogen atom, R ₂ represents a hydrogen atom, a halogen atom or a methyl group optionally substituted with a halogen atom, and R ₃ represents isopropyl A secondary butyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a tert-butyl group or a 1,1-dimethylpropyl group, R ₄ represents an oxygen atom or a sulfur atom, and R ₅ represents C1
-C5 alkyl group, C2-C5 alkynyl group or C3
Represents a ＣC5 alkenyl group. And a pyrazolinone derivative represented by the formula (1) as an active ingredient. 2. The method according to claim 1, wherein the plant, the cultivation area of the plant, or the seed of the plant is N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide,
-(3,5-dichlorophenyl) -N- (1-methylethyl) -2,4-dioxo-1-imidazolidinecarboxamide and 3- (3,5-dichlorophenyl) -5
Methyl-5-vinyl-1,3-oxazolidine-2,4
A method for controlling plant diseases, which comprises applying at least one imide compound selected from -dione and the pyrazolinone derivative according to claim 1.