JPS59210004A - Agricultural and horticultural fungicidal composition - Google Patents

Abstract

PURPOSE:An agricultural and horticultural fungicidal composition having high effect even with a low concentration, capable of preventing fungi resistant to chemicals from spreading, obtained by combining an aniline derivative with any of a benzimidazole fungicide, thiophanate fungicide, and cyclic imide fungicide. CONSTITUTION:One or more of aniline derivatives shown by the formula I [X is nitro, amino, thioisocyanato, group shown by the formula II, or group shown by the formula III (A' and A'' are O, or S; R<2> is alkyl, alkenyl, etc.); Y is alkyl, alkoxy, H, halogen, acyl, etc.; R1 is alkyl, alkenyl, alkynyl, etc.; A is O, or S; B is alkyl, alkenyl cycloalkyl, phenyl, etc.] are blended with one or more selected from a benzimidazole, thiophanate, and cyclic imide fungicides to give a fungicidal composition. The fungicidal shows sufficient controlling effect when both fungi resistant to chemicals and susceptible fungi are present.

Description

DETAILED DESCRIPTION OF THE INVENTION This product 1 is a compound of the general formula Yamahachi [wherein, ” -1'Lz represents a group 1 (represents an oxygen atom or a sulfur atom, R2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group or lower alkoxyalkyl group); Y is A lower alkyl group, a lower alkoxyl group, a lower alkoxylcarbonyl group, a hydrogen atom, a halokene atom or an acyl group.R1 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a lower cyclo Represents an alkylalkyl group or a lower cyanoalkyl 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 substituent represented by the general formula -W-R3 (Here, W represents an oxygen atom or a sulfur atom, R53 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a lower cycloalkyl group. or represents a phenyl group which may be substituted with a halogen atom, or a halokene atom, a cyano group, a phenyl group, a lower cycloalkyl group, a lower alkokyne group, a lower alkenylokyne group, a lower haloalkoxy group, a phenoxy group or (Represents an alkyl group substituted with at least one atom or group of an aralkyloxy group.) 1 m or more of the aniline derivative represented by the above, and a benzimidazole fungicide, thiophanate fungicide, or cyclic imide fungicide. The present invention relates to an agricultural and horticultural fungicidal composition containing 1% or more selected from the following as an active ingredient.

Penzimitazole fungicides and thiophanate fungicides (hereinafter referred to as benzimida-nol-thiophanate fungicides) have shown excellent control effects against various pathogenic bacteria that parasitize agricultural and horticultural crops, and have been in use since around 1970. It is widely used as a fungicide for agricultural and horticultural purposes, and has greatly contributed to increased crop production. However, when these fungicides are continuously sprayed on crops, drug-resistant bacteria often spread, reducing the control effectiveness of the fungicides, making them practically unusable. If spraying a fungicide does not produce the desired control effect and prevent disease outbreaks, farmers and other fungicide users will suffer severe damage. Furthermore, it is known that bacteria that are resistant to any of the benzimiguduran thiophanate fungicides are also resistant to other fungicides in this group, exhibiting so-called cross-resistance. However, in a field where no pest control effect is observed even if Benozoru is sprayed, no control effect can be expected even if other henzimitazole-thiophanate fungicides are sprayed.

In fields where drug-resistant bacteria are prevalent, we have no choice but to stop using penzimitazole/thiophanate fungicides.
There are many known cases in which the density of drug-resistant bacteria does not decrease even if use is discontinued, and once drug-resistant bacteria occur, they will be affected for a long time. In addition, in such fields, drug-resistant bacteria exhibit cross-resistance, and the target disease can be controlled by spraying other types of fungicides. There are very few species that show pesticidal effects, making accurate pest control difficult.

In addition, cyclic imide fungicides are effective against various plant diseases, especially gray mold, but the benzimidazole and
Similar to thiophanate fungicides, there are problems with ξ-resistant bacteria.

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

However, in actual fields where pathogens are prevalent, drug-resistant bacteria and wild bacteria (hereinafter referred to as
They are called susceptible bacteria. It is often sufficient to use either a benzimidazole/thiophanate fungicide, a cyclic imide fungicide, or an aniline derivative represented by the general formula [I] above alone. It is difficult to expect significant disease control effects. Therefore, as a result of further various studies, we found that the control effect could be improved by using a mixture of one or more aniline derivatives and one or more benzimidazole/thiophanate fungicides or cyclic imide fungicides. It became clear that the temperature was higher even at extremely low temperatures than when they were used alone.

Therefore, the composition of the present invention has high practical value as a fungicide that exhibits excellent pest control effects. Furthermore, the composition of the present invention can be used to continuously spray benzimidazole-thiophanate fungicides or cyclic imide fungicides in fields where drug-resistant bacteria have not appeared, even if there is concern about the spread of drug-resistant bacteria. It is possible to prevent its appearance.

Table 1 shows examples of the aniline derivatives represented by the general formula [il.

In addition, examples of the above-mentioned benzimidazole fungicides include methyl l-(butylcarbamoyl)benzimidazole-2-yl-bamate (hereinafter referred to as compound A) represented by the formula % formula % [ 2-(4-thiazolyl)benzimidazole (hereinafter referred to as 458 compound B), methylbenzimidazol-2-ylcarbamate represented by the formula (hereinafter referred to as compound C), represented by the formula There is 2-(z-furirumbensimitazole (hereinafter referred to as compound)), and as a thiophanate fungicide, the formula:

1,2-bis(3-methoxycarbonyl-2) represented by 1 1
-Thioureidrabenzene (hereinafter referred to as compound E)
, formula)) 1,2-his(3-ethoxycarbonyl-2
-Thioureido)benzene (hereinafter referred to as compound F)
, 2-(0,S-dimethylphosphorylamine) of the formula SCH3
-1-(3'-methoxycarbonyl-27-thioureitonobenzene (hereinafter referred to as compound G)), 2-(0,0-dimethylthiophosphorylamino) -1-(8'- There is methoxycarbonyl-2-thioureido)benzene (hereinafter referred to as compound 11), and as a cyclic imide fungicide, for example, N-(8', 5'-dichlorophenyl)-1,2-dimethyl shown by the formula Cyclopropane 1.2-carboximide (hereinafter referred to as compound ■), 8-(3', 5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2 represented by the formula
,4-dione (hereinafter referred to as compound J), 8-(8',5'-dichlorophenyl)-5-methyl-5-hinyloxazolidine-2,4-
dione (hereinafter referred to as compound), ethyl (RS)-3-(8', 5'
-dichlorophenyl)-5-)f-2,4-dioxoxazolidine-5-carboxylate (hereinafter referred to as compound).

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

An example of such a disease/ff1id is the powdery mildew fungus of apples (Podosphaera Leouco).
tricha), Venturia 1na
equalis), Scleroti
nia mali), oyster anthracnose fungus (clbeo
spsrium k, aki), peach blight fungus (
Sclero-inia cinerea), Cladosporium carpoph-
ilum), grape fungus Botrytis
cinerea), Elsiroe
ampeline), late rot fungus (Glomerell
a cingulata), sugar beet brown spot fungus (C
ercospora beticala), peanut brown spot fungus (Cercospora arachidi)
cola), Cercos-pora p.
ersonata), powdery mildew fungus (Er
Ysiphe gramininis f, sp,
hordei), eye six spot fungus (Cercos
porella herpotrichoides)
, 1'usarium n1vale
), Erysiphe gr.
arrunla f, sp, tritici),
Cucumber powdery mildew fungus (5phaerotheca)
ful 1g1nea), vine blight fungus (Mycosp
Haerel la melonis), Botrytis cinerea, Botrytis cinerea (
C1adospor iumcucumer inee
m), tomato leaf mold fungus (Cladospor-i
Botrytis
cinerea), powdery mildew fungus (5ph
aerotheca humul i).

HotryLis ciner of hops
ea) , Erysiph
e cichoracearum ), CD1plocarpon rosae ), mandarin orange scab (Elsinoe, fawcetti)
Penicillium itali
cum), green mold fungus (Pen1c ill inm)
d ig i thtum) etc.

On the other hand, it has also been found that the composition of the present invention is highly safe for humans, livestock, and fish, and can be chopped into agriculturally useful crops and used without causing any practical harm. When actually applying the composition of the present invention, the aniline derivative represented by the general formula [11] may be prepared in a commonly used form such as a powder, wettable powder, oil, emulsion, tablet, granule, or fine granule. It is formulated into miniazole, floraful, etc., and applied by diluting with water together with commercially available fungicides of Compounds A-L in the form of wettable powders.

Examples of formulations are shown below.

Formulation Example 1 Powder 2 parts of compound (2), 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 180 parts of wettable powder compound f3, 45 parts of diatomaceous earth, 20 parts of white carpon, 3 parts of wetting agent (sodium lauryl sulfate) and 2 parts of dispersing agent (calcium lignin sulfonate) are thoroughly pulverized and mixed, the base ingredient content is 30. % hydration agent.

Formulation Example 8 Wettable powder compound +715 (1 part, 45 parts of diatom, 2.5 seconds of wetting agent (calcium alkylbenzene sulfonate) and 25 parts of dispersing agent (calcium lignin sulfonate) were thoroughly ground and mixed. Obtain a hydrating powder.

Formulation Example 4 Emulsion compound +8+ 10 parts, cyclohexanone 80 parts and emulsifier (polyoxyethylene alkyl allyl ether)
A mixing deviation of 10@ produces an emulsion with a main ingredient content of IO%.

In the above preparation, a general active compound is superimposed and 1.0
~95.0%, preferably 2.0-80.0%.

Further, the composition of the present invention is usually 10 to 100 per 10 ares.
The amount of p applied is appropriate. Furthermore, the concentration used is 0.0
The range of 0.05% to 0.5% is desirable, but the amount used,
Since the degree varies depending on the formulation, application time, method, location, target disease, target crop, etc., there is no problem in increasing or decreasing it 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, 5-1-
Butyl-5-1-+-tert-butylbenzyldithiocarbonimidate, 0.0-dimethyl 0-(2,
6-dichloro-4-methyltuunyl) phosphorothioate, N-trichloromethylthio-4-cyclohexene-1,2-cyclohexene-1,2-cycloheximide, polyoxysilane, streptomynon, cycloethylene hiscythioca-bamate, tetrachloroisophthalonitrile, 8-Hydroxyquinoli, pe'-dichlorofluoromethylthio N, N-
Dimethyl-N'-7enylsulfamide, ■-(4-chlorophenoxy)-8,8-dimethyl-1-(1,2,
4-) Fungicides such as lyazol-■-yl)-2-butanone, methyl N-(2,6-dijfulfenyl)-N-, ;'l-xyacetyl-2-methylglycinate, aluminum ezalphosphite, etc. , phenoxy herbicides such as 2゜-4-dikuenoxyacetic acid, phenyl ether herbicides such as 2,4-dichlorophenyl 4'-21-phenyl ether, 2-dichlorophenyl 4,6 −
Triazine herbicides such as hisnitylamino-1.8.5-) riazine, 8-(8,4-dichlorophenyl)-1
, urea-based herbicides such as l-dimethylurea, carbamate-based herbicides such as inpropyl N-(3-chlorophenyl)carbamate, and thiol carbamate-based herbicides such as 5-(4-chlorobenzyl)N,N-diethylthiol carbamate. herbicides, acid anilide herbicides such as 3,4-dichloropropionanilide, uracil herbicides such as 5-bromo-3-5ec-butyl-6-methyluracil, ■, l'
-Pyridinium salt herbicides such as dimethyl-4,4'-hypyridinium chloride, N-(phosphonomethyl)chrysine, 0-ethyl-〇-(2-nitro-5-methylphenyl)N-sec-butyl phosphoroamide thio ate or phosphorus herbicides such as 5-(2-methyl-1-piperidylcarbonylmethyl)0.0-di-n-propyldithiophosphate, QJ, Q! , α-trifluoro-2,6
-Toluidine herbicides such as Sinitro N,N-dipropyl-p-)luidine, organophosphorus insecticides such as 0,0-dimethyl〇-(4-nitro-3-methylphenyl)phosphorothioate, α-cyano-3 -Phenoxybenzyl 2
-(4-chlorophenyl)invalerate, 8-phenoxybenzyl 2゜2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate, α-cyano-3-fairtskidibenzyl 2,2-dimethyl- +3
- Can be used in combination with pyrethroid insecticides such as (2,2-dibromovinyl) dichloropropanecarboxylate, without reducing the control effect of each agent alone, and furthermore, the combination can have a synergistic effect. This is to be expected.

Next, a test example will be presented to further clarify the usefulness of the composition of the present invention as a fungicide for common use in farms.

Test Example 1 Cucumber Powdery Mildew Control Effect A sufficient amount of droplets of an emulsion of an aniline derivative with a sandbox number, a hydrating agent of compounds A to H, and a water diluted solution of a mixture thereof were attached to the leaf surface in a 9Qme plastic pot. The grass was sprayed until After the chemical solution is air-dried, the seedlings are infected with cucumber powdery mildew fungus (Sphaer).
A mixture of drug-resistant and susceptible bacteria of Otheca fuliginea was obtained, and the disease state was observed.

5. The number of lesions was calculated by the following method.

That is, depending on the appearance of lesions on the investigated leaves, U, (+, 6,
The lesions were classified into indexes of 1 and 2.4, and the lesions were calculated using the following formula17.

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

05 - 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 less than 20% of the leaf area.

2. Bacterial flora or lesions are observed on less than 50% of the leaf area on the dyed surface.

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

Next, the control value was calculated using the following formula.

As a result, as shown in Table 2, aniline derivatives and compound A
When mixed with any of ~H and sprayed, a superior control effect was observed compared to when they were sprayed alone. Table 2 Test Example 2 Tomato gray mold control effect 90-liter plastic product Add the emulsion of the aniline conductor of the following compound numbers, the hydrating agents of compounds ■ to L, and the water diluted solutions of their mixtures in sandy loam per pot.
Ex foliage was sprayed. After air-drying the chemical solution, gray mold fungus (Bot
A conidial liquid obtained by mixing drug-resistant and susceptible bacteria of S. rytiscinerea was inoculated by injection.

The specimens were left 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 ■.

As a result, as shown in Table 3, aniline derivatives and compounds I,
J, K1. When sprayed in a mixture with either of the following, a superior pest control effect was obtained compared to when either of them was sprayed alone.

Table 8 //(AOIN 47/20 47/38 43/78 47/18 3152 47/34 57/14 37/32 3150 43/76) (A 01 N 47/22 47/38 43/78 7718 3152 47 /34 57/14 37/32 3150 43/76 ) 0 inventor Kato Sube 4-2-1 Takashi, Takarazuka City Sumitomo Chemical Co., Ltd. 0 inventor Hiroshi Noguchi 4-2-1 Takashi, Takarazuka City Inventor: Yukio Oguri, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd. Inventor: Shigeo Yamamoto, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd. Author: Katsuzo Kamoshita, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd. Amendment (voluntary) February 7, 1980 Commissioner of the Patent Office Kazuo Wakasugi 1, Indication of the case 1988 Patent Application No. 220450 2, Name of the invention: Agricultural and horticultural fungicidal composition 3, Relationship with the person making the amendment Case Patent applicant address: 5-15 Kitahama, Higashi-ku, Osaka Name (
209) Sumitomo Chemical Co., Ltd. Representative Hijikata
Take 4, Agent Address: 5-15-5 Kitahama, Higashi-ku, Osaka, Claims column of the specification subject to amendment and Detailed Description of the Invention column 6, Contents of the amendment (1) Scope of claims. Correct as shown in the attached sheet.

(2) Insert the following between the 7th line from the bottom and the 6th line from the bottom of page 28 of the specification.

"Formulation Example 5 Powder If 1 part of compound (1), 1 part of compound (1), 88 parts of clay and 10 parts of talc are thoroughly ground and mixed, the main ingredient content will be 2%.
Get the powder.

Formulation Example 6 Wettable powder Compound C86) 20 parts, Compound (J) 10 parts, diatomaceous earth 45 parts, white carbon 20 parts, wetting agent (sodium lauryl sulfate) 3 parts and dispersing agent (calcium lignin sulfonate) 2 parts were mixed well. By pulverizing and mixing, a wettable powder with a base ingredient content of 30% is obtained.

Formulation Example 7 Wettable powder Compound (1) 10 parts, Compound (A) 40 parts, diatomaceous earth 4.
5 parts, 2.5 parts of a wetting agent (calcium alkylpenozenosulfonate), and 2.5 parts of a dispersing agent (calcium ligninsulfonate) are thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 50%. ” Claims General formula [wherein, 1 8' (where A' and A // are the same or different,
It represents an oxygen atom or a sulfur atom, and R2 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group. )
. Y represents a lower alkyl group, a lower alkoxyl group, a lower alkoxycarbonyl group, a hydrogen atom, a halogen atom, or an acyl group. R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a lower cycloalkylalkyl group or a lower cyanoalkyl 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 substituent represented by the general formula -W-R3. (here,
W represents an oxygen atom or a sulfur atom, and R3 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a lower cycloalkyl group, or is substituted with a halogen atom. represents a phenyl group, or /'% at least one of a halogen atom, a cyano group, a phenyl group, a lower cycloalkyl group, a lower alkoxyl group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, or an aralkyloxy group. The two atoms represent an alkyl group substituted with a group. ). ] Agricultural and horticultural use characterized by containing as active ingredients one or more of the aniline derivatives shown below and one or more of a benzimitazole fungicide, a thiophanate aging agent, or a cyclic imide fungicide. Sterilizing composition.

Procedural supplementary statement (voluntary) February 17, 1980 Kazuo Wakasugi, Commissioner of the Patent Office 1. Indication of the case 1981 Patent application No. 220450 2. Name of the invention: Agricultural and horticultural fungicidal composition 3. Amended. Person related to the person’s case Address of applicant 5-15 Kitahama, Higashi-ku, Osaka Name (2
09) Sumitomo Chemical Co., Ltd. Representative Hijikata
Take 4, Agent address: 5-15-5 Kitahama, Higashi-ku, Osaka, Detailed description of the invention in the specification subject to amendment 6 Contents of amendment (]) In Table 1 of Specification No. 15J6, compound number ( 42
) physical constant lζI-1,,78(q, 2JJ
(-6 and 50J are respectively l-2-78 (t2
■)'', corrected as l'-7,50j.

that's all

Claims (1)

[Claims] In the general formula C, X is a nitro group, an ami7 group, a thioisocyanato group, or a group represented by the general formula -NH-C-Rx1 A' or -NH-C-L→2. ' represents (where A' and N' are the same or different,
It represents an oxygen atom or a sulfur atom, and R2 represents a lower alkyl group, a lower alkenyl group, a lower alkenyl group, a lower haloalkyl group or a lower alkoxyalkyl group. )
. Y is a lower alkyl group, a lower alkoxyl group, a lower alkoxycarbonyl group, a hydrogen atom, a halogen atom or an acyl group. R] is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, Represents a lower alkoxyalkyl group, a lower cycloalkylalkyl group, or a lower cyanoalkyl 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 of the general formula -W -Represents a substituent represented by R3 (where W represents an oxygen atom or a sulfur atom, R3 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group,
Represents a lower haloalkynyl group or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or a halogen atom, a cyan group,
Phenyl group, lower cycloalkyl group, lower alkoxyl group, lower alkenyloxy group, lower haloalkoxy group,
It represents an alkyl group substituted with at least one atom or group of a phenoxy group or an aralkyloxy group. ). A fungicidal composition for agriculture and horticulture, comprising as active ingredients one or more of the aniline derivatives shown in ] and one or more of a benzimidazole fungicide, a thiophanate fungicide, or a cyclic imide fungicide. .