KR20210046650A - Amide compounds and their uses - Google Patents

Abstract

식 (A) 로 나타내는 화합물은, 식물 병해에 대하여 우수한 방제 효력을 갖는다.The present invention provides a compound having an excellent control effect against plant diseases.

The compound represented by formula (A) has an excellent control effect against plant diseases.

Description

Amide compounds and their uses

This application claims priority to Japanese Patent Application No. 2018-153851 for which it applied on August 20, 2018, and its benefits, the entire contents of which are incorporated herein by reference.

The present invention relates to amide compounds and their uses.

Conventionally, in order to control plant diseases, various compounds have been developed and provided for practical use (see Non-Patent Document 1). In Patent Document 1, formula (B) as an intermediate for producing an insecticide

[Formula 1]

The compound represented by (hereinafter, referred to as compound B) is described.

US Patent Application Publication No. 2017/0158682 Specification

The Pesticide Manual-17th edition (published by BCPC) ISBN 978-1-901396-88-1

An object of the present invention is to provide a compound having an excellent control effect against plant diseases.

The present invention is as follows.

(1) Formula (A)

[Formula 2]

The compound represented by (hereinafter, referred to as compound A).

[2] A composition containing the compound according to [1] and an inert carrier.

[3] A method for controlling plant diseases by treating plants or soil with an effective amount of the compound according to [1].

According to the present invention, plant diseases can be controlled.

The composition of the present invention contains Compound A and an inert carrier. In the composition of the present invention, compound A is usually mixed with an inert carrier such as a solid carrier or a liquid carrier, and if necessary, a surfactant and other formulation aids are added to prepare an emulsion, an emulsion, and It is formulated into powder, granule, hydration, granule hydration, flowable, dry flowable, microcapsule, and the like.

The composition of the present invention generally contains 0.0001 to 95% by weight of the compound A.

As a solid carrier used at the time of formulation, for example, clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur, etc.) Activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), etc., and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, etc.) , Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, etc.). have.

As a liquid carrier, for example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.) , Esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, etc.), sulfoxide Sides (dimethyl sulfoxide, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.) are mentioned.

Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates. Can be lifted.

Examples of other adjuvants for formulations include fixing agents, dispersants, coloring agents, and stabilizers, specifically, for example, casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers ( Polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol and A mixture of 3-tert-butyl-4-methoxyphenol) is mentioned.

Compound A has an effect against plant pathogens. The following are mentioned as a plant disease derived from a plant pathogen. In parentheses, the scientific name of the pathogen causing the disease is indicated.

Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), leaf sheath blight (Rhizoctonia solani), Gibberella fujikuroi, Sclerophthora macrospora; Wheat powdery mildew (Blumeria graminis), red fungal disease (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), red tongue rust (Puccinia recondita) Microdochium nivale, Microdochium majus), Small sulcus sulcus (Typhula incarnata, Typhula ishikariensis), Ustilago tritici, Tilletia caries (Tilletia controversa), Pseudocercosporella herpotrichoid disease (Pseudocercosporella herpotrichoid disease) ), Macular disease (Pyrenophora tritici-repentis), Rhizoctonia solani, Rhizoctonia solani, Gaeumannomyces graminis; Powdery mildew of barley (Blumeria graminis), red fungal disease (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia hordei), spot rust ( Puccinia hordei), Ustilago nuda, Rhynchosporium secalis, Pyrenophora teres, Cochliobolus sativus, Pyrenophora graminea, Lamularia collo-cygni ), Rhizoctonia solani caused by bacteria of the genus Rhizoctonia; Corn rust (Puccinia sorghi), southern rust (Puccinia polysora), soot spot (Setosphaeria turcica), tropical rust (Physopella zeae), sesame leaf blight (Cochliobolus heterostrophus), anthrax (Colletotrichum graminicola), gray leaf spot disease (Cercospora) zeae-maydis), brown blotches (Kabatiella zeae), Paeosphaeria leaf spot disease (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpella macrospora, stem rot (Fusarium graminearum, Fusaragoium verticilioides, Colletotrichum graminicola), Blotch disease (Ustildis) ; Cotton anthrax (Colletotrichum gossypii), white fungal disease (Ramularia areola), black spot disease (Alternaria macrospora, Alternaria gossypii), Black root rot disease (Thielaviopsis basicola) caused by the genus Thielaviopsis; Rust of coffee (Hemileia vastatrix), leaf spot disease (Cercospora coffeicola); Rapeseed sclerotic disease (Sclerotinia sclerotiorum), black spot disease (Alternaria brassicae), root rot disease (Phoma lingam); Rust of sugar cane (Puccinia melanocephela, Puccinia kuehnii); Sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Citrus sunspot disease (Diaporthe citri), Elsinoe fawcetti, fruit rot (Penicillium digitatum, Penicillium italicum), plague (Phytophthora parasitica, Phytophthora citrophthora); Apple flower rot (Monilinia mali), ovary (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), Ventricia inaequalis, anthrax (Glomerella cingulata), brown spotted disease (Diplocarmalis) ), double blotch (Botryosphaeria berengeriana), plague (Phytophtora cactorum); Ventricle disease (Venturia nashicola, Venturia pirina), black spot disease (Alternaria alternata Japanese pear pathotype), red disease (Gymnosporangium haraeanum); Peach gray blotches (Monilinia fructicola), plague (Cladosporium carpophilum), pomopsis rot (Phomopsis sp.); Elsinoe ampelina, Glomerella cingulata, Uncinula necator, Phakopsora ampelopsidis, Black rot disease (Guignardia bidwellii), Plasmopara viticola; Persimmon anthrax (Gloeosporium kaki), deciduous (Cercospora kaki, Mycosphaerella nawae); Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown blotches (Corynespora cassiicola), Fusarium oxysporum (Fusarium oxysporum), Downy mildew (Pseudopersora, Pseudopersora) Wearing bottle (Pythium sp.); Tomato double blotch (Alternaria solani), leaf fungus (Cladosporium fulvum), soot fungus (Pseudocercospora fuligena), plague (Phytophthora infestans), powdery mildew (Leveillula taurica); Eggplant brown blotches (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); Black spot disease (Alternaria japonica), vitiligo (Cercosporella brassicae), root lump disease (Plasmodiophora brassicae), downy mildew (Peronospora parasitica) of cruciferous vegetables; Green onion rust (Puccinia allii); Cercospora kikuchii, Elsinoe glycines, sunspot disease (Diaporthe phaseolorum var. sojae), rust disease (Phakopsora pachyrhizi), brown layer disease (Corynespora cassiicola), anthrax (Colletotrichum glycines) , Leaf rot (Rhizoctonia solani), brown blotch (Septoria glycines), spot blotch (Cercospora sojina), sclerotic disease (Sclerotinia sclerotiorum), powdery mildew (Microsphaera diffusa), stem blight (Phytophthora sojae), Downy mildew (Peronospora), Sudden death (Peronospora) (Fusarium virguliforme); Kidney bean sclerotic disease (Sclerotinia sclerotiorum), rust disease (Uromyces appendiculatus), gait disease (Phaeoisariopsis griseola), anthrax (Colletotrichum lindemuthianum); Peanut's black blotch (Cercospora personata), brown blotch (Cercospora arachidicola), white silk disease (Sclerotium rolfsii); Powdery mildew of peas (Erysiphe pisi); Potato rot (Alternaria solani), Plague (Phytophthora infestans), Scarlet rot (Phytophthora erythroseptica), Spongospora subterranean f. dahliae, Verticillium nigrescens); Strawberry powdery mildew (Sphaerotheca humuli); Tea's reticulum (Exobasidium reticulatum), people's disease (Elsinoe leucospila), leprosy (Pestalotiopsis sp.), anthrax (Colletotrichum theae-sinensis); Tobacco disease (Alternaria longipes), anthrax (Colletotrichum tabacum), Downy mildew (Peronospora tabacina), Plague (Phytophthora nicotianae); Brown blotches (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root root disease (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides), rust disease (Uromyces betae); Rose black (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Chrysanthemum brown blotches (Septoria chrysanthemi-indici), white rust (Puccinia horiana); Onion vitiligo (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), micrococcal rot (Botrytis squamosa); Sclerotinia sclerotiorum, Pythium ultimum of various crops; Radish black blotches (Alternaria brassicicola); Dollar spot disease on grass (Sclerotinia homoeocarpa), Brown patch disease on grass and Rhizoctonia solani; And banana cigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia. Disease. Virus diseases of various crops mediated by genus Polymixa or genus Olpidium.

Rice seedling bacterial disease (Burkholderia plantarii); Cucumber spot bacterial disease (Pseudomonas syringae pv. lachrymans); Eggplant green blight (Ralstonia solanacearum), citrus ulcer disease (Xanthomonas citiri); Cabbage soft rot (Erwinia carotovora), etc.

The method for controlling plant diseases of the present invention includes, for example, treatment of plants such as foliage spreading and seed disinfection; The treatment on the cultivation area of plants, such as soil treatment, is mentioned.

The treatment amount of Compound A is usually 1 to 10000 g per 1000 m 2. When Compound A is formulated as an emulsion, a wettable agent, a flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.01 to 10000 ppm and applied, and granules, powders, etc. are usually applied as they are.

The composition of the present invention can be used as a control agent for plant diseases in agricultural lands such as fields, rice paddies, lawns and orchards.

Example

Hereinafter, the present invention will be described in more detail with reference to production examples, test examples, and the like, but the present invention is not limited to these examples.

First, the preparation example of compound A is shown.

4-(trifluoromethanesulfonyl)benzene-1,2-diamine can be prepared by the method described in US Patent No. 656367. 3-(ethanesulfonyl)pyridine-2-carbonyl chloride can be prepared by the method described in US Patent Application Publication No. 2017/0158682.

In a nitrogen atmosphere, to a mixture of 5.00 g of 4-(trifluoromethanesulfonyl)benzene-1,2-diamine and 50 g of tetrahydrofuran, 4.71 g of 3-(ethanesulfonyl)pyridine-2-carbonyl chloride and A mixture of 4.71 g of xylene was added dropwise, and the mixture was stirred at room temperature for 7 hours. The obtained mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 2.25 g of compound A.

Shows a ¹ H-NMR data of the compound A in the following.

Next, a test example is shown. No treatment in Test Example 1 means that Compound A was not dispersed. In addition, the non-treatment group in Test Examples 2 and 3 means a sphere that performs the same operation as that of the treatment group except that the compound A is not used.

Test Example 1

The plastic pot was filled with soil, and cucumbers (variety; Sagamihanjiro) were sown, and grown in a greenhouse for 19 days. 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wet silica (weight ratio 1: 1), 20 parts of Compound A, and 45 parts of water were sufficiently mixed. The obtained mixture was diluted with water to prepare a diluted solution containing 500 ppm of Compound A. The diluted solution was sprayed so that it adhered sufficiently to the leaf surface of the cucumber. After spraying, the plants were air-dried, and 1 day later, an aqueous suspension of cucumbers and pathogens (Pseudoperonospora cubensis) was spray-inoculated. After inoculation, it was left at 23° C. for 1 day under high humidity, and then cultivated in a greenhouse at 24° C. during the day and 20° C. during the night for 6 days, and then the lesion area was investigated. As a result, the lesion area in the cucumber treated with Compound A was 30% or less of the lesion area in the untreated cucumber.

Test Example 2

After dispensing 1 ml of a dimethyl sulfoxide solution containing a predetermined concentration of Compound A into the wells of a titer plate (96 wells), 150 µl of a potato bath liquid medium containing a colony of Phytophthora capsici was dispensed. , Compound A was prepared so that the final concentration was 100 ppm, and a treatment group was obtained. Further, an untreated section was prepared in another well. After this plate was incubated at 27°C for 3 days to proliferate gourd gray blight bacteria, the absorbance at 600 nm of each well of the titer plate was measured, and the growth rate of the gourd gray blots was determined. Based on the growth degree, the effect was calculated using "Equation 1".

「Equation 1」

Effect (%) = 100 × (X-Y)/X

X: Growth degree of bacteria in the untreated area

Y: Growth degree of bacteria in the treated area

As a result, the effect was 60%.

Test Example 3

After dispensing 1 µl of a dimethyl sulfoxide solution containing a predetermined concentration of Compound A into the wells of a titer plate (96 wells), 150 µl of Chapek medium containing a mycelial fragment of Pythium ultimum was dispensed, and Compound A Was prepared so that the final concentration was 100 ppm, and it was set as a treatment section. Further, an untreated section was prepared in another well. After this plate was incubated at 23°C for 5 days to proliferate the wearing bacteria, the absorbance at 600 nm of each well of the titer plate was measured, and the growth degree of the wearing bacteria was determined. Based on the growth degree, the effect was calculated using "Equation 1". As a result, the effect was 73%.

Comparative Test Example 1

In place of the compound A, the compound B was used, and the test was conducted according to Test Example 1. As a result, the lesion area in the cucumber treated with Compound B was 75% or more of the lesion area in the untreated cucumber.

Comparative Test Example 2

In place of the compound A, the compound B was used, and the test was carried out according to Test Example 2. As a result, the effect was 26%.

Comparative Test Example 3

In place of the compound A, the compound B was used, and the test was carried out according to Test Example 3. As a result, the effect was 5%.

Industrial applicability

Compound A exhibits an excellent control effect against plant diseases.

Claims (3)

Equation (A)

Compound represented by. A composition containing the compound according to claim 1 and an inert carrier. A method for controlling plant diseases by treating plants or soil with an effective amount of the compound according to claim 1.