JPS59161301A - Fungicidal composition for agriculture and horticulture - Google Patents

Abstract

PURPOSE:A fungicidal composition for agriculture and horticulture comprising a specific aniline derivative and benzimidazole fungicide, etc. as active ingredients, showning more improved fungicidal effect on fungi resistant or sensitive to agents than in a case wherein each of the active ingredients is used individually. CONSTITUTION:A composition containing an aniline derivative shown by the formula (X and Y are alkylene, or alkoxyalkylene; k, l, m, and n are 0 or 1; R1 is alkyl, alkoxy, H, halogen, etc., Z is H, alkyl, alkenyl, etc.; A is O, or S; B is alkyl, phenyl, etc.) showing selectively fungicidal effect on fungi resistant to agents, and a benzimidazole fungicide, thiophanate fungicide or cyclic imide fungicide as active ingredients. Application of the composition to fields having fungi resistance to agents can control both fungi resistant to agents and fungi sensitive to them, and application of it to fields having no fungi resistant to agents can prevent occurrence of fungi resistant to agents.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is represented by the general formula [C] [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxyalkylene group. k +
L, rn and n are the same or different and represent 0 or 1. R1 represents lower alkyl M, <i-class alkoxyl group, lower alkoxymethyl & lower alkoxycarbonyl group, hydrogen atom, halogen atom, acyl group, or cyano group. 2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a (Jl'flJ alkoxycarbonylalkyl group, or the general formula -C-R2 or -
Indicates a group represented by 8-Rs. (Here, R1 represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group, and R3 represents a lower alkyl group, a phenyl group, or a lower alkoxycarbonyl group.) A represents an oxygen atom or a sulfur atom. B represents a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or a group represented by the general formula -W-4. (Here, W represents an oxygen atom or a sulfur atom. R4
represents a lower alkenyl group, a lower alkynyl group, an alkynyl group, a lower haloalkenyl group, a lower cycloalkyl group, or a phenyl group optionally substituted with a halogen atom, or a halogen atom, a cyano represents a lower alkyl group which may be substituted with a phenyl group, a lower cycloalkyl group, or a lower alkoxy group. 〉] This relates to a disinfectant composition for official use in farms, which contains as active ingredients one or more of the aniline derivatives shown in the following, and one or more selected from benzimidazole fungicides, thiophanate fungicides, or cyclic imide fungicides. be.

Benzimidazole-based fungicides and thiophanate-based fungicides (hereinafter referred to as benzimidazole-thiophanate-based fungicides) are effective against various diseases that parasitic JIA on agricultural and horticultural crops.
It exhibits an excellent control effect against fungi and has been widely used as a fungicide for agricultural and horticultural purposes since around 1970, and has greatly contributed to increased crop production. However, when these fungicides are continuously sprayed on crops, drug-resistant bacteria spread, reducing the control effectiveness of the fungicides, often making them unusable. If spraying a fungicide does not have the expected control effect and the outbreak of the disease cannot be suppressed, the damage to farmers and other users of the fungicide will be enormous. Furthermore, it is known that bacteria that are resistant to any of the benzimidazole/thiophanate fungicides are also resistant to other fungicides in this group, exhibiting so-called cross-resistance. Therefore, for example, in a field where no pesticidal effect is observed even after spraying Benomyl, no pesticidal effect can be expected even if other benzimidazole/thiophanate fungicides are sprayed. In fields where drug-resistant bacteria are prevalent, the use of benzimidazole/thiophanate fungicides must be discontinued, but there are many known cases in which the density of drug-resistant bacteria does not decrease even after discontinuing their use. Once drug resistance develops, the effects will be felt for a long time. In addition, in such fields, the target disease is controlled by spraying other fungicides to which drug-resistant bacteria do not show cross-resistance, but benz-imidazole/thiophanate fungicides are not effective. There are very few species that show a pesticidal effect, making accurate pest control difficult.

In addition, cyclic imide fungicides are effective against various plant diseases, especially gray mold, but the benzimidazole and
There are similar problems with resistant bacteria with thiophanate fungicides.

Taking the above circumstances into consideration, the present inventors made earnest efforts to invent a bactericidal agent that exhibits a selective bactericidal effect against drug-resistant bacteria, and as a result, they discovered an aniline derivative represented by the general formula [I,].

However, in actual TM fields where pathogenic bacteria are prevalent, drug-resistant bacteria and wild bacteria that are susceptible to benzimidazole thiono-1nate fungicides or cyclic imide fungicides (hereinafter referred to as susceptible bacteria) are present. In many cases, a mixture of benzimidazole/thiophanate fungicides, cyclic imide fungicides, or the aniline derivatives represented by the general formula [D] alone does not have a sufficient disease control effect. It is difficult to expect. Therefore, as a result of further various studies, it was found that one or more aniline derivatives, benzimidazole, thiophane, 1-series fungicides, or rings are higher even at lower degrees.

Therefore, the composition of the present invention has high practical value as a fungicide that exhibits an excellent pest control effect.

Furthermore, the composition of the present invention can be applied by continuously spraying a benzimidazole thiophanate fungicide or a cyclic imide fungicide in a field where drug-resistant bacteria have not appeared.
Even if there is a concern about the spread of drug-resistant bacteria, their appearance can be prevented.

Aniline derivatives represented by the general formula [I] are illustrated in Table 1.

＼ Examples of benzimidazole fungicides include methyl 1-(butylcarbamoyl)benzimidazole-2-yl-bamate (hereinafter referred to as F1 compound A) represented by the formula %, 2-( represented by the formula 4-thiazolyl)benzimidazole (hereinafter referred to as compound B), methylbenzimidazole-2-ylbamate (hereinafter referred to as compound C) represented by the formula, 2-(2-furyl) represented by the formula There are benzimidazoles (hereinafter referred to as compounds), and examples of thionate fungicides include 1 shown by the formula
, 2-bis(3-methoxycarbonyl-2-thioureido)benzene (hereinafter referred to as compound E), represented by the formula 1.2-bis(3-ethoxycarbonyl-2
-Thioureido)benzene (hereinafter referred to as compound F)
, 2-(0,s-dimethylphosphorylamino) represented by the formula
-1-(3'-methoxycarbonyl-2'-thioureido)benzene (hereinafter referred to as compound G), 2-(U, (J-・dimethylthioposborylamino) -1-(8 '-Methoxycarbonyl-2-thioureido)benzene (hereinafter referred to as compound R), and examples of cyclic imide fungicides include N-(8',5'-dichlorophenyl)- 1
, 2-dimethylcyclopropane-1,2-carboximide (hereinafter referred to as compound engineering), 8-(8', 5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2 represented by the formula
, 4-dione (hereinafter referred to as compound J), 8-(8',5'-dichlorophenyl)-5 represented by the formula
-Methyl-5-vinyloxazolidine-2゜4-dione (hereinafter referred to as compound), ethyl (
xLS) -s-(8', 5'-dichlorophenyl)-5-methyl-2,4-dioxoxazolidine-5-carboxylate (hereinafter referred to as compound).

Since the composition of the present invention has excellent bactericidal activity against a wide variety of filamentous fungi, it can be used to control various pathogens occurring in agriculture and horticulture.

Examples of such pathogens include powdery mildew of apples (Podospbaera leucotric).
ha), Venturja 1nneq
ualis), Monilia disease (5clerotini)
a mali), oyster anthracnose fungus (Gloeospo
riumkaki), peach gray blight fungus (8clero
tinia cinerea), Clad
osportum carpophilum ), Botrytis cinerea
), Elsinoe ampelin
a), late rot fungus
lata), sugar beet brown spot fungus (Cercosp)
orabetrcalg), Beannut brown spot fungus (
Cercospora arachidicola)
, Uercospora personat
a), barley powdery mildew fungus (ErySlphe)
gramtnxs t.

sp, horciei), Eye C spot fungus (U
ercosporellaherpotrLchoid
es), crimson N'14 N fungus (Fusarlum
n1vale), powdery mildew of wheat (1>ry
sjphe graminio f, sp.

trstici), powdery mildew of cucumber (8ph
aerothecafuliginea), vine blight (MycosphaercHa melonis),
Gray mold fungus (BoLrytis oinerea)
, C1adosporiurn cucum
erjneem), tomato leaf mold fungus (Olado
sporium fulvum), gray mold fungus (
J3 otrytis cincrea), strawberry powder/b mildew fungus (8 phaerotheca humul)
i), Botrytis c.
inerea), powdery mildew of tobacco (Erysj.
pbecicl+oracearun), Diplocarpon rosae, E18inoe fawcett
, i), Blue mold fungus (Penicilliumit)
aHcum), Green mold fungus (Penicilliu)
Examples include m digitturn).

On the other hand, it has been found that the composition of the present invention is still safe for humans, livestock, and fish, and can be used without actually causing any harm to agriculturally useful crops. When actually applying the composition of the present invention, for example, the aniline derivative represented by the general formula [I] may be used in a commonly used form such as a powder, an aqueous phase, an oil, an emulsion, a tablet, a granule, an m-grain, etc. It is formulated into a powder, aerosol, flowable, etc., and applied together with a commercially available fungicide of compounds A-L in the form of wettable powders, diluted with water.

Examples of formulations are shown below.

Formulation Example 1 Powder 2 parts of compound (5), 88 parts of clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder with a base ingredient content of 2%.

Formulation Example 2 If 80 parts of water phase agent compound (29), 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate) and 2 parts of dispersing agent (calcium lignin sulfonate) are thoroughly ground and mixed, the base agent will be contained. A quantity of 30% hydrating agent is obtained.

Formulation Example 3 50 parts of aqueous phase agent compound (30), 45 parts of diatomaceous earth, 2.5 parts of a wetting agent (calcium alkylbenzenesulfonate), and 2.5 parts of a paralyzing dispersant (calcium ligninsulfonate) are thoroughly ground and mixed to form the main agent. An aqueous phase agent containing 50% Mi is obtained.

Formulation Example 4 Emulsion If you mix 10 parts of compound (31), 80 parts of cyclohexanone, and 10 parts of emulsifier (polyoxyethylene alkyl allyl ether), the main ingredient will be contained! A 10% emulsion is obtained.

The above formulations generally contain from 1.0 to 1.0% by weight of active compound.
95.0%, preferably 2.0-80.0%. In addition, the composition of the present invention usually has 10 to ioog per 10 ares.
The application amount is appropriate.

Furthermore, the concentration used is preferably in the range of 0.005% to 0.5%, but the amount and concentration used depend on the dosage form, application period,
Since it varies depending on the method, location, target disease, target crop, etc., there is no problem in increasing or decreasing the amount without being limited to the above range.

Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides.

For example, S-n-butyl S-p-tert
-Butylbenzyldithiocarbonimidate, 0°O-
Dimethyl 0-(2,6-dichloro-4-methylphenyl)phosphorothioate, hetrichloromethylthio 4
-Cyclohexene-1゜2-dicarboximide, polyoxin, streptomycin, zinc ethyl, dithiocarbamate, tetrachloroisophthalonitrile, 8-hydroxyquinoline NJ-dichlorofluoromethylthio-N,N-dimethyl-N'-phenylsulfami do, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-1 riazol-1-yl) -
Bactericidal agents such as 2-'y-tanone, methyl N-(2,6-dimethylphenyl)-N-methoxyacetyl-2-methylglycinate, aluminum ethyl phosphite, 2
.

Phenoxy thread removal um such as 4-dichlorophenoxyacetic acid,
2. Diphenyl ether herbicides such as 4-dichlorophenyl 4'-nitrophenyl ether, 2-chloro-4,
Triazine herbicides such as 6-pisethylamino-1,8,5-triazine, 3-(8,4-dichlorophenyl)
- Urea herbicides such as 1゜l-dimethylurea, carbamate herbicides such as isopropyl N-(8-chlorophenyl)carbamate, 8 (4-ri).

thiol carbamate herbicides such as N,N-diethylthiol carbamate, acid anilide herbicides such as 8゜4-dichloropropionanilide, and 5-bromo-B-sea-butyl-6-methyluracil. Uracil-based H removers, pyridinium base herbicides such as 1゜1'-dimethyl-4,4'-bipyridinium chloride, N-
(°phosphonomethyl)glycine, 0-ethyl U-(27
Phosphorous herbicides such as nitro (5-methylphenyl) N-see-butyl phosphoroamide thioate or 5-(2-methyl-1-piperidylcarbonylmethyl)0°0-di-n-propyldithiophosphate, α, α, α-trifluoro2゜6-sinitro N,N-dipropyl-
Toluidine herbicides such as p-toluidine, organophosphorus insecticides such as 0.0-dimethyl (J-(4-nitro-3-methylphenyl) phosphorothioate), α-cyano-3-
Phenoxyhensyl 2-(4-chlorophenyl)isovalerate, 3-phenoxybenzyl 2,2-dimethyl-
8-(2,2 dichlorovinyl)cyclopropanecarboxylate, σ-cyano 3-phenoxybenzyl 2゜2
It can be used in combination with pyrethroid insecticides such as -dimethyl-8-(2,2-dibromovinyl) dichloropropanecarboxylate, without reducing the control effect of each single agent. Furthermore, a synergistic effect by mixing is also expected.

Next, test examples will be given to further clarify the usefulness of the composition of the present invention as an agricultural and horticultural fungicide.

Test Example 1 Cucumber Powdery Mildew Control Effect A 90ml plastic pot was filled with sandy loam, and cucumbers (variety:
Recombinant half day) was sown. This was cultivated at room temperature for 8 days to obtain cucumber seedlings with weak cotyledons. Formulation example 4 for this seedling
An emulsion of an aniline derivative having the following compound number, a hydrating powder of compound A-fi, and a water diluted solution of a mixture thereof prepared according to the following were sprayed on foliage until a sufficient amount of droplets adhered to the leaf surface. After air-drying due to chemical reasons (seedling knee t-t cucurbit powdery mildew @ (S
A conidial suspension obtained by mixing drug-resistant and susceptible bacteria of P. phaerothecafuliginea was inoculated by spraying. The plants were placed in a greenhouse and cultivated for 10 days to develop the disease, and then the disease state was observed.

The disease severity was calculated by the following method.

In other words, depending on the appearance of lesions on the leaves, 0°0.5.1
, 2.4, and the disease severity was calculated using the following formula.

(Sickness index) (Sickness status) 0...
No bacterial flora or lesions are observed on the leaf surface.

0.5: Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area.

1: Bacterial flora or lesions are observed on the leaf surface in less than 20% of the leaf area.

2... Clusters or lesions are observed on the leaf surface covering less than 50% of the leaf area.

4...Bacterial flora or lesions are observed on the leaf surface over 50% of the leaf area.

Next, calculate the pest control value using the following formula.

As a result, as shown in Table 2, aniline derivatives and compound A
, 13. Mix with O, D, E, F, G, fi? 5, a superior pest control effect was observed compared to when they were sprayed alone.

Table 2 Test Example 2 Tomato gray mold control effect A plastic bottle with a capacity of 90 rnl was filled with sandy loam,
Sow tomatoes (variety: Fukuju No. 2). This was cultivated for 4J in a bath room to obtain tomato sprouts at the 4-leaf stage. To this, an emulsion of the aniline derivative of compound number 4 prepared according to Formulation Example 4, a water diluted solution of a wettable powder of compounds 1 to L, and a mixture thereof were sprayed on 10 leaves per pot. After air-drying, gray mold fungus (J3otrytis01ner)
A conidial liquid obtained by mixing drug-resistant bacteria 1 and susceptible 1 was inoculated by spraying.

The specimens were kept in a humid room at 20°C for 5 days, and then the disease state was observed.

The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.

As a result, as shown in Table 3, aniline derivatives and compounds I,
When sprayed in combination with J, L, or L, a superior control effect was obtained compared to when they were sprayed alone.

Table 3 □ 1 (5) + 4. ,” l lo
o.

10+2Q, 1 − 1−−m−−−−−−−−−−1−−
1--11<80) + Ic], 0 +2
Q □ Joo :j ]
-(1(31)-1-1110+20 1 1
00:1 I・1(3o+J:lO+20 1 100 1:□ Continued from page 1 ■,・Inventor Hiroshi Noguchi 4-2-1 Takashi, Takarazuka City Inventor Hisabe Kato, Sumitomo Chemical Co., Ltd. 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd. Internal procedure amendment (voluntary) 1 Case indication il
Name of the invention: Agricultural and horticultural fungicidal composition 3 Supplementary i1. ．． Relationship with the case involving a person who does
(209) Representative of Sumitomo Chemical Industries, Ltd.
Takeshi Hijikata 4, Agent Address: 5-15 Kitahama, Higashi-ku, Osaka, Detailed Description of the Invention of Specification 6 Subject to Amendment 6, Contents of Amendment (1) Line 6 from the bottom of page 7 of the specification to the eyes [and them]
Correct the statement to ``Also, the pesticidal effect is on those.'' f21 'Ii'i, page 24, insert a line between the 2nd excerpt. , 11 parts of the compound, 8 parts of clay, and 10 parts of talc were thoroughly ground and mixed to form a mixture containing the base agent and 2 parts of talc.
Obtain % powder.

Formulation Example 6 Wettable powder compound (31) 20 parts, compound JIO part, fl 814
5 parts of honoid carbon, 20 parts of humectant carbon, 3 parts of wetting agent (sodium lauryl sulfate), and 2 parts of calcium lignin sulfonate are thoroughly ground and mixed to hydrate 302 parts of water containing the main ingredient. get the agent.

Formulation Example 7 Wettable powder compound (29) 10 parts, compound A 40 parts, diatomaceous earth 4
5 parts of a wetting agent (calcium alkyl benzene sulfonate) and 25 parts of a dispersing agent (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 50%. ” or more = 11-

Claims (1)

[Claims] General formula [wherein X and Y are the same or different and represent a lower 7-rukylene group or a lower alkoxyalkylene group. k
, z, m and n are the same or different, and represent [) or l. R1 is a lower alkyl group, a lower alkoxyl group, a lower alkoxymethyl group, QN, 17! Alkoxycarbonyl group, hydrogen atom, halogen atom, anru group or sia/
Indicates the group. Z is Mizu ζ Nahiko, 'J-E class alkyl! The formula is (class alkenyl 21, fji; class alkenyl group,
Lower alkoxycarbonylalkyl group, or general formula -
07ft2. ;) or a group represented by -8-ribs. (Here, R2 represents a lower alkyl group, a lower cycloalkyl group, or an enyl group, and R8 represents a lower alkyl group,
Indicates a phenyl group or a lower alkoxycarbonyl group. )
A represents an oxygen atom or a sulfur atom. B represents lower alkyl i, a lower alkyl group, a lower cycloalkyl group, a phenyl group, or a group represented by the general formula -W-R4. (Here, Wli acid cumulative atom, haloalkenyl group, lower cycloalkyl group, or phenyl group optionally substituted with halogen atom, or halogen atom, cyano group, phenyl group, lower cycloalkyl group) Indicates a lower alkyl group which may be substituted with an alkyl group or a lower alkoxy group)] 1M or more of the aniline derivative represented by the formula and one type of benzimidazole fungicide, thiophanate fungicide, or cyclic imide fungicide. A patented synergistic sterilizing composition characterized by containing the above as active ingredients.