JP7250022B2 - Amide compound and use thereof - Google Patents

Description

This application claims priority to and benefits from Japanese Patent Application No. 2018-153851 filed on August 20, 2018, the entire contents of which are incorporated into this application by reference.
The present invention relates to amide compounds and uses thereof.

で示される化合物（以下、化合物Ｂと記す）が記載されている。Conventionally, various compounds have been developed for controlling plant diseases and put into practical use (see Non-Patent Document 1). Patent Document 1 discloses the formula (B) as an intermediate for producing an insecticide

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

U.S. Patent Application Publication No. 2017/0158682

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 excellent control efficacy against plant diseases.

で示される化合物（以下、化合物Ａと記す）。
〔２〕 〔１〕に記載の化合物と、不活性担体とを含有する組成物。
〔３〕 〔１〕に記載の化合物の有効量を植物又は土壌に処理することによる、植物病害の防除方法。The present invention is as follows.
[1] Formula (A)

The compound represented by (hereinafter referred to as compound A).
[2] A composition containing the compound of [1] and an inert carrier.
[3] A method for controlling plant diseases, which comprises applying an effective amount of the compound of [1] to plants or soil.

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

The composition of the present invention contains Compound A and an inert carrier. The composition of the present invention is usually produced by mixing compound A with an inert carrier such as a solid carrier or liquid carrier, adding a surfactant and other formulation aids as necessary, and preparing an emulsion, oil, It is formulated into powders, granules, wettable powders, wettable granules, flowables, dry flowables, microcapsules and the like.
The composition of the present invention usually contains 0.0001 to 95% by weight of Compound A.

Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) polyester resins, nylon-6, nylon-11, nylon-66 and other nylon resins, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).

Examples of liquid carriers include 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.), sulfoxides (dimethyl sulfoxide, etc.), and Vegetable oils (soybean oil, cottonseed oil, etc.) can be mentioned.

Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers and polyethylene glycol fatty acid esters, and anionic surfactants such as alkylsulfonates, alkylbenzenesulfonates and alkylsulfates. Surfactants are included.

Other formulation adjuvants include sticking agents, dispersing agents, coloring agents and stabilizers. Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Compound A has efficacy against plant pathogens. Plant diseases derived from plant pathogens include the following. Parentheses indicate the scientific name of the pathogen causing the disease.

rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bananae (Gibberella fujikuroi), yellow dwarf disease (Sclerophthora macrospora); wheat powdery mildew (Blumeria) graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Puccinia striiformis, Puccinia graminis, Puccinia recondita, Microdochium nivale , Microdochium majus), Snow rot (Typhula incarnata, Typhula ishikariensis), Naked smut (Ustilago tritici), Forage smut (Tilletia caries, Tilletia controversa), Eye spot (Pseudocercosporella herpotrichoides), Downy mildew ( Stagonospora nodorum, Pyrenophora tritici-repentis, Rhizoctonia solani, Gaeumannomyces graminis; Blumeria graminis, Fusarium graminearum , Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia hordei), rot (Puccinia hordei), naked smut (Ustilago nuda), Rhynchosporium secalis, Pyrenophora teres, Cochliobolus sativus, Pyrenophora graminea, Ramularia collo-cygni, wilt caused by Rhizoctonia ( Rhizoctonia solani); corn rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty blight (Setosphaeria turcica), tropical rust (Physopella zeae), leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), Gray leaf spot (Cercospora zeae-maydis), Brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpella macrospora, Stokerot disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis); cotton anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot caused by Thielaviopsis spp. (Thielaviopsis basicola); coffee rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); Rust (Puccinia melanocephela, Puccinia kuehnii); sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora); Venturia inaequalis, Glomerella cingulata, Diplocarpon mali, Botryosphaeria berengeriana, Phytophtora cactorum; Venturia nashicola, Venturia pirina, black spot ( Alternaria alternata Japanese pear pathotype, Gymnosporangium haraeanum; Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp.; Elsinoe ampelina, Late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), blacklot (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), leaf litter Diseases (Cercospora kaki, Mycosphaerella nawae); anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), fusarium oxysporum ), Pseudoperonospora cubensis, Phytophthora capsici, Pythium sp.; Alternaria solani, Cladosporium fulvum, Pseudocercospora fuligena ), Phytophthora infestans, Leveillula taurica; Phomopsis vexans, Erysiphe cichoracearum; Alternaria japonica, Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica); green onion rust (Puccinia allii); soybean purpura (Cercospora kikuchii), black spot (Elsinoe glycines), black spot (Diaporthe phaseolorum) var. sojae), rust (Phakopsora pachyrhizi), brown spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), speck ( Cercospora sojina, Sclerotinia sclerotiorum, Microsphaera diffusa, Phytophthora sojae, Peronospora manshurica, Fusarium virguliforme; sclerotiorum), rust (Uromyces appendiculatus), horn spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum); powdery mildew of peas (Erysiphe pisi); summer blight of potatoes (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery mildew (Spongospora subterranean f. sp. subterranea), Hemi-wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens); Strawberry powdery mildew (Sphaerotheca humuli); Tea net blister (Exobasidium reticulatum), Elsinoe leucospira, Ring spot (Pestalotiopsis sp. ), anthracnose (Colletotrichum theae-sinensis); tobacco scab (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); sugar beet brown spot (Cercospora) beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), cochlioides (Aphanomyces cochlioides), rust (Uromyces betae); rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Chrysanthemum brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); onion white spot (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), microsclerotium rot Sclerotinia sclerotiorum of various crops, Pythium ultimum; Alternaria brassicicola of radish; Dollar spot of turf (Sclerotinia homoeocarpa), brown patch of turfgrass and large patch disease (Rhizoctonia solani); and sigatoka disease of bananas (Mycosphaerella fijiensis, Mycosphaerella musicola).
Seed diseases or early growth of various crops caused by fungi of the genus Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc. disease. Viral diseases of various crops mediated by the genus Polymixa or Olpidium.
Bacterial seedling blight of rice (Burkholderia plantarii); cucumber spot (Pseudomonas syringae pv. lachrymans); eggplant wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citiri); carotovora) etc.

The method for controlling plant diseases of the present invention includes, for example, plant treatments such as foliage spraying and seed disinfection; and plant cultivation land treatments such as soil treatment.

The processing amount of compound A is usually 1 to 10000 g per 1000 m ² . When Compound A is formulated as an emulsion, wettable powder, flowable preparation, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.01 to 10000 ppm, and granules, powders, etc. is usually applied as is.

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

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

First, a production example of compound A is shown.
4-(Trifluoromethanesulfonyl)benzene-1,2-diamine can be prepared by the method described in US Pat. No. 6,566,367. 3-(ethanesulfonyl)pyridine-2-carbonyl chloride can be produced by the method described in US Patent Application Publication No. 2017/0158682.

In a nitrogen atmosphere, 4.71 g of 3-(ethanesulfonyl)pyridine-2-carbonyl chloride and 4.71 g of xylene were added to a mixture of 5.00 g of 4-(trifluoromethanesulfonyl)benzene-1,2-diamine and 50 g of tetrahydrofuran. was added dropwise and stirred at room temperature for 7 hours. The resulting mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 2.25 g of Compound A.
¹ H-NMR data of Compound A are shown below.
¹ H-NMR (CDCl ₃ ) δ(ppm): 8.87 (1H, dd), 8.57 (1H, s), 8.48 (1H, dd), 7.88 (1H, d), 7.72 (2H, m), 6.90 ( 1H, d), 5.16 (2H, s), 3.82 (2H, q), 1.36 (3H, t).

Next, test examples are shown. "No treatment" in Test Example 1 means that Compound A was not sprayed. In addition, the non-treated plots in Test Examples 2 and 3 mean plots in which the same operation as the treated plots was performed except that compound A was not used.

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

Test example 2
After dispensing 1 μL of a dimethyl sulfoxide solution containing a predetermined concentration of compound A into wells of a titer plate (96 wells), 150 μL of a potato decoction liquid medium containing Phytophthora capsici zoospores was dispensed. , Compound A was prepared to have a final concentration of 100 ppm, and was used as a treatment plot. Also, an untreated group was prepared in another well. After culturing this plate at 27° C. for 3 days to proliferate Cucurbitaceae botrytis, the absorbance at 600 nm of each well of the titer plate was measured to determine Cucurbitaceae botrytis growth rate. Based on the degree of growth, the efficacy was calculated using "formula 1".
"Formula 1"
Efficacy (%) = 100 x (XY)/X
X: Growth rate of bacteria in untreated plot Y: Growth rate of bacteria in treated plot As a result, the efficacy 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 Czapek medium containing mycelial fragments of Pythium ultimum was dispensed, and compound A was terminated. It was prepared to have a concentration of 100 ppm, and was used as a treatment section. Also, an untreated group was prepared in another well. After culturing this plate at 23° C. for 5 days to grow the take-off fungus, the absorbance at 600 nm of each well of the titer plate was measured to determine the growth rate of take-off fungus. Based on the degree of growth, the efficacy was calculated using "formula 1". As a result, the efficacy was 73%.

Comparative test example 1
A test was performed according to Test Example 1 using compound B in place of compound A. As a result, the lesion area in the compound B-treated cucumber was 75% or more of the lesion area in the untreated cucumber.

Comparative test example 2
A test was performed according to Test Example 2 using compound B in place of compound A. As a result, the efficacy was 26%.

Comparative test example 3
A test was performed according to Test Example 3 using compound B in place of compound A. As a result, the efficacy was 5%.

Compound A exhibits an excellent control effect against plant diseases.

Claims (3)

Formula (A)

A compound represented by A composition comprising a compound of claim 1 and an inert carrier. A method for controlling plant diseases by applying an effective amount of the compound according to claim 1 to plants or soil.