KR20210046650A - Amide compounds and their uses - Google Patents
Amide compounds and their uses Download PDFInfo
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- KR20210046650A KR20210046650A KR1020217001146A KR20217001146A KR20210046650A KR 20210046650 A KR20210046650 A KR 20210046650A KR 1020217001146 A KR1020217001146 A KR 1020217001146A KR 20217001146 A KR20217001146 A KR 20217001146A KR 20210046650 A KR20210046650 A KR 20210046650A
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- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
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- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- 239000002385 cottonseed oil Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 208000038015 macular disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
본 출원은 2018년 8월 20일에 출원된 일본 특허출원 제2018-153851호에 대한 우선권 및 그 이익을 주장하는 것으로, 그 전체 내용은 참조함으로써 본 출원에 편입된다.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.
본 발명은 아미드 화합물 및 그 용도에 관한 것이다.The present invention relates to amide compounds and their uses.
종래, 식물 병해를 방제하기 위해 여러 가지의 화합물이 개발되어 있고, 실용에 제공되고 있다 (비특허문헌 1 참조). 특허문헌 1 에는, 살충제의 제조 중간체로서 식 (B)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
[화학식 1][Formula 1]
로 나타내는 화합물 (이하, 화합물 B 라고 기재한다) 이 기재되어 있다.The compound represented by (hereinafter, referred to as compound B) is described.
본 발명은, 식물 병해에 대하여 우수한 방제 효력을 갖는 화합물을 제공하는 것을 과제로 한다.An object of the present invention is to provide a compound having an excellent control effect against plant diseases.
본 발명은, 이하와 같다.The present invention is as follows.
〔1〕 식 (A)(1) Formula (A)
[화학식 2][Formula 2]
로 나타내는 화합물 (이하, 화합물 A 로 기재한다).The compound represented by (hereinafter, referred to as compound A).
〔2〕〔1〕에 기재된 화합물과, 불활성 담체를 함유하는 조성물.[2] A composition containing the compound according to [1] and an inert carrier.
〔3〕〔1〕에 기재된 화합물의 유효량을 식물 또는 토양에 처리하는 것에 의한, 식물 병해의 방제 방법.[3] A method for controlling plant diseases by treating plants or soil with an effective amount of the compound according to [1].
본 발명에 의해, 식물 병해를 방제할 수 있다.According to the present invention, plant diseases can be controlled.
본 발명의 조성물은, 화합물 A 와 불활성 담체를 함유한다. 본 발명의 조성물은, 통상적으로 화합물 A 와 고체 담체, 액체 담체 등의 불활성 담체를 혼합하고, 필요에 따라 계면 활성제, 그 밖의 제제용 보조제를 첨가하여, 유제 (乳劑), 유제 (油劑), 분제, 입제 (粒劑), 수화제, 과립 수화제, 플로어블제, 드라이 플로어블제, 마이크로 캡슐제 등으로 제제화된다.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.
본 발명의 조성물은, 화합물 A 를 통상적으로 0.0001 ∼ 95 중량% 함유한다.The composition of the present invention generally contains 0.0001 to 95% by weight of the compound A.
제제화시에 사용되는 고체 담체로는, 예를 들어 점토류 (카올린 클레이, 규조토, 벤토나이트, 산성 백토 등), 건식 실리카, 습식 실리카, 탤크, 세라믹, 그 밖의 무기 광물 (세리사이트, 석영, 황, 활성탄, 탄산칼슘 등), 화학 비료 (황산암모늄, 인산암모늄, 질산암모늄, 우레아, 염화암모늄 등) 등의 미분말 및 입상물 등, 그리고 합성 수지 (폴리프로필렌, 폴리아크릴로니트릴, 폴리메타크릴산메틸, 폴리에틸렌테레프탈레이트 등의 폴리에스테르 수지, 나일론-6, 나일론-11, 나일론-66 등의 나일론 수지, 폴리아미드 수지, 폴리염화비닐, 폴리염화비닐리덴, 염화비닐-프로필렌 공중합체 등) 를 들 수 있다.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.
액체 담체로는, 예를 들어 물, 알코올류 (메탄올, 에탄올 등), 케톤류 (아세톤, 메틸에틸케톤 등), 방향족 탄화수소류 (톨루엔, 자일렌 등), 지방족 탄화수소류 (헥산, 시클로헥산 등), 에스테르류 (아세트산에틸, 아세트산부틸 등), 니트릴 류 (아세토니트릴 등), 에테르류 (디이소프로필에테르, 디에틸렌글리콜디메틸에테르 등), 아미드류 (N,N-디메틸포름아미드 등), 술폭사이드류 (디메틸술폭사이드 등), 및 식물유 (대두유, 면실유 등) 를 들 수 있다.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.
계면 활성제로는, 예를 들어 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌알킬아릴에테르, 폴리에틸렌글리콜 지방산 에스테르 등의 비이온 계면 활성제, 및 알킬술폰산염, 알킬벤젠술폰산염, 알킬황산염 등의 음이온 계면 활성제를 들 수 있다.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.
그 밖의 제제용 보조제로는, 고착제, 분산제, 착색제 및 안정제 등, 구체적으로는 예를 들어 카세인, 젤라틴, 당류 (전분, 아라비아검, 셀룰로오스 유도체, 알긴산 등), 리그닌 유도체, 벤토나이트, 합성 수용성 고분자 (폴리비닐알코올, 폴리비닐피롤리돈, 폴리아크릴산류 등), 산성 인산이소프로필, 2,6-디-tert-부틸-4-메틸페놀, BHA (2-tert-부틸-4-메톡시페놀과 3-tert-부틸-4-메톡시페놀의 혼합물) 를 들 수 있다.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.
화합물 A 는, 식물 병원균에 대하여 효력을 갖는다. 식물 병원균에서 유래하는 식물 병해로는, 이하의 것을 들 수 있다. 괄호 안은, 그 병해를 일으키는 병원균의 학명을 나타낸다.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.
벼의 도열병 (Magnaporthe grisea), 참깨잎마름병 (Cochliobolus miyabeanus), 잎집무늬마름병 (Rhizoctonia solani), 벼키다리병 (Gibberella fujikuroi), 누른오갈병 (Sclerophthora macrospora) ; 밀의 흰가룻병 (Blumeria graminis), 붉은 곰팡이병 (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), 황녹병 (Puccinia striiformis), 흑녹병 (Puccinia graminis), 적녹병 (Puccinia recondita), 홍색 설부병 (Microdochium nivale, Microdochium majus), 설부 소립균핵병 (Typhula incarnata, Typhula ishikariensis), 겉깜부기병 (Ustilago tritici), 비린깜부기병 (Tilletia caries, Tilletia controversa), 안점병 (Pseudocercosporella herpotrichoides), 밀껍질 마름병 (Stagonospora nodorum), 황반병 (Pyrenophora tritici-repentis), 리족토니아속균에 의한 묘입고병 (苗立枯病) (Rhizoctonia solani), 입고병 (立枯病) (Gaeumannomyces graminis) ; 보리의 흰가룻병 (Blumeria graminis), 붉은 곰팡이병 (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), 황녹병 (Puccinia striiformis), 흑녹병 (Puccinia graminis), 적녹병 (Puccinia hordei), 점녹병 (Puccinia hordei), 겉깜부기병 (Ustilago nuda), 구름무늬병 (Rhynchosporium secalis), 망반병 (Pyrenophora teres), 반점병 (Cochliobolus sativus), 반엽병 (Pyrenophora graminea), 람라리아 리프 스폿병 (Ramularia collo-cygni), 리족토니아속균에 의한 묘입고병 (Rhizoctonia solani) ; 옥수수의 녹병 (Puccinia sorghi), 남방 녹병 (Puccinia polysora), 그을음무늬병 (Setosphaeria turcica), 열대성 녹병 (Physopella zeae), 참깨잎마름병 (Cochliobolus heterostrophus), 탄저병 (Colletotrichum graminicola), 그레이 리프 스폿병 (Cercospora zeae-maydis), 갈색무늬병 (Kabatiella zeae), 파에오스파에리아 리프 스폿병 (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpella macrospora, 줄기썩음병 (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), 깜부기병 (Ustilago maydis) ; 목화의 탄저병 (Colletotrichum gossypii), 흰색 곰팡이병 (Ramularia areola), 흑반병 (Alternaria macrospora, Alternaria gossypii), Thielaviopsis 속균에 의한 Black root rot 병 (Thielaviopsis basicola) ; 커피의 녹병 (Hemileia vastatrix), 리프 스폿병 (Cercospora coffeicola) ; 유채씨의 균핵병 (Sclerotinia sclerotiorum), 흑반병 (Alternaria brassicae), 뿌리썩음병 (Phoma lingam) ; 사탕수수의 녹병 (Puccinia melanocephela, Puccinia kuehnii) ; 해바라기 녹병 (Puccinia helianthi), 노균병 (Plasmopara halstedii) ; 감귤류의 흑점병 (Diaporthe citri), 더뎅이병 (Elsinoe fawcetti), 과실 부패병 (Penicillium digitatum, Penicillium italicum), 역병 (Phytophthora parasitica, Phytophthora citrophthora) ; 사과의 꽃썩음병 (Monilinia mali), 부란병 (Valsa ceratosperma), 흰가룻병 (Podosphaera leucotricha), 반점 낙엽병 (Alternaria alternata apple pathotype), 흑성병 (Venturia inaequalis), 탄저병 (Glomerella cingulata), 갈색무늬병 (Diplocarpon mali), 겹무늬병 (Botryosphaeria berengeriana), 역병 (Phytophtora cactorum) ; 배의 흑성병 (Venturia nashicola, Venturia pirina), 흑반병 (Alternaria alternata Japanese pear pathotype), 적성병 (Gymnosporangium haraeanum) ; 복숭아의 잿빛무늬병 (Monilinia fructicola), 흑성병 (Cladosporium carpophilum), 포몹시스 부패병 (Phomopsis sp.) ; 포도의 새눈무늬병 (Elsinoe ampelina), 만부병 (Glomerella cingulata), 흰가룻병 (Uncinula necator), 녹병 (Phakopsora ampelopsidis), 블랙 로트병 (Guignardia bidwellii), 노균병 (Plasmopara viticola) ; 감의 탄저병 (Gloeosporium kaki), 낙엽병 (Cercospora kaki, Mycosphaerella nawae) ; 박류의 탄저병 (Colletotrichum lagenarium), 흰가룻병 (Sphaerotheca fuliginea), 덩굴마름병 (Didymella bryoniae), 갈색무늬병 (Corynespora cassiicola), 덩굴쪼김병 (Fusarium oxysporum), 노균병 (Pseudoperonospora cubensis), 역병 (Phytophthora capsici), 묘입고병 (Pythium sp.) ; 토마토의 겹무늬병 (Alternaria solani), 잎곰팡이병 (Cladosporium fulvum), 그을음곰팡이병 (Pseudocercospora fuligena), 역병 (Phytophthora infestans), 흰가룻병 (Leveillula taurica) ; 가지의 갈색무늬병 (Phomopsis vexans), 흰가룻병 (Erysiphe cichoracearum) ; 십자화과 야채의 흑반병 (Alternaria japonica), 백반병 (Cercosporella brassicae), 뿌리혹병 (Plasmodiophora brassicae), 노균병 (Peronospora parasitica) ; 파의 녹병 (Puccinia allii) ; 대두의 자주무늬병 (Cercospora kikuchii), 새눈무늬병 (Elsinoe glycines), 흑점병 (Diaporthe phaseolorum var. sojae), 녹병 (Phakopsora pachyrhizi), 갈색겹무늬병 (Corynespora cassiicola), 탄저병 (Colletotrichum glycines, Colletotrichum truncatum), 엽부병 (Rhizoctonia solani), 갈색무늬병 (Septoria glycines), 점무늬병 (Cercospora sojina), 균핵병 (Sclerotinia sclerotiorum), 흰가룻병 (Microsphaera diffusa), 줄기 역병 (Phytophthora sojae), 노균병 (Peronospora manshurica), 돌연사병 (Fusarium virguliforme) ; 강낭콩의 균핵병 (Sclerotinia sclerotiorum), 녹병 (Uromyces appendiculatus), 각반병 (Phaeoisariopsis griseola), 탄저병 (Colletotrichum lindemuthianum) ; 땅콩의 검은무늬병 (Cercospora personata), 갈색무늬병 (Cercospora arachidicola), 흰비단병 (Sclerotium rolfsii) ; 완두의 흰가룻병 (Erysiphe pisi) ; 감자의 하역병 (Alternaria solani), 역병 (Phytophthora infestans), 주홍색 부패병 (Phytophthora erythroseptica), 가루더뎅이병 (Spongospora subterranean f. sp. subterranea), 반신 위조병 (半身萎凋病) (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens) ; 딸기의 흰가룻병 (Sphaerotheca humuli) ; 차의 그물떡병 (Exobasidium reticulatum), 백성병 (Elsinoe leucospila), 윤반병 (Pestalotiopsis sp.), 탄저병 (Colletotrichum theae-sinensis) ; 담배의 적성병 (Alternaria longipes), 탄저병 (Colletotrichum tabacum), 노균병 (Peronospora tabacina), 역병 (Phytophthora nicotianae) ; 사탕무의 갈색무늬병 (Cercospora beticola), 엽부병 (Thanatephorus cucumeris), 근부병 (Thanatephorus cucumeris), 검은뿌리병 (Aphanomyces cochlioides), 녹병 (Uromyces betae) ; 장미의 흑성병 (Diplocarpon rosae), 흰가룻병 (Sphaerotheca pannosa) ; 국화의 갈색무늬병 (Septoria chrysanthemi-indici), 흰녹병 (Puccinia horiana) ; 양파의 백반 엽고병 (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), 회색 부패병 (Botrytis allii), 소균핵성 부패병 (Botrytis squamosa) ; 각종 작물의 균핵병 (Sclerotinia sclerotiorum), 입고병 (Pythium ultimum) ; 무우 검은무늬병 (Alternaria brassicicola) ; 잔디의 달러 스폿병 (Sclerotinia homoeocarpa), 잔디의 브라운 패치병 및 라지 패치병 (Rhizoctonia solani) ; 그리고 바나나의 시가토카병 (Mycosphaerella fijiensis, Mycosphaerella musicola).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 속, Penicillium 속, Fusarium 속, Gibberella 속, Tricoderma 속, Thielaviopsis 속, Rhizopus 속, Mucor 속, Corticium 속, Phoma 속, Rhizoctonia 속, 및 Diplodia 속균 등에 의해 야기되는, 각종 작물의 종자 병해 또는 생육 초기의 병해. Polymixa 속 또는 Olpidium 속 등에 의해 매개되는 각종 작물의 바이러스병.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.
벼의 묘입고 세균병 (Burkholderia plantarii) ; 오이의 반점 세균병 (Pseudomonas syringae pv. lachrymans) ; 가지의 풋마름병 (Ralstonia solanacearum), 감귤의 궤양병 (Xanthomonas citiri) ; 배추의 연부병 (Erwinia carotovora) 등.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.
본 발명의 식물 병해의 방제 방법은, 예를 들어 경엽 산포, 종자 소독 등의 식물체에 대한 처리 ; 토양 처리 등의 식물의 재배지에 대한 처리를 들 수 있다.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.
화합물 A 의 처리량은, 1000 ㎡ 당 통상적으로 1 ∼ 10000 g 이다. 화합물 A 가 유제 (乳劑), 수화제, 플로어블제 등으로 제제화되어 있는 경우에는, 통상적으로 유효 성분 농도가 0.01 ∼ 10000 ppm 이 되도록 물로 희석시켜 시용하고, 입제, 분제 등은, 통상적으로 그대로 시용한다.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.
본 발명의 조성물은, 밭, 무논, 잔디밭, 과수원 등의 농경지에 있어서의 식물 병해의 방제제로서 사용할 수 있다.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.
실시예Example
이하, 본 발명을 제조예, 및 시험예 등에 의해 더욱 상세하게 설명하는데, 본 발명은 이들 예에만 한정되는 것은 아니다.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.
먼저, 화합물 A 의 제조예를 나타낸다.First, the preparation example of compound A is shown.
4-(트리플루오로메탄술포닐)벤젠-1,2-디아민은, 미국 특허 제6566367호 명세서에 기재된 방법으로 제조할 수 있다. 3-(에탄술포닐)피리딘-2-카르보닐클로라이드는, 미국 특허출원 공개 제2017/0158682호 명세서에 기재된 방법으로 제조할 수 있다.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.
질소 분위기하에서, 4-(트리플루오로메탄술포닐)벤젠-1,2-디아민 5.00 g 및 테트라하이드로푸란 50 g 의 혼합액에, 3-(에탄술포닐)피리딘-2-카르보닐클로라이드 4.71 g 및 자일렌 4.71 g 의 혼합물을 적하하고, 실온에서 7 시간 교반하였다. 얻어진 혼합물을 감압하에서 농축하고, 잔류물을 실리카 겔 칼럼 크로마토그래피에 부여하여, 화합물 A 를 2.25 g 얻었다.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.
화합물 A 의 1H-NMR 데이터를 이하에 나타낸다.Shows a 1 H-NMR data of the compound A in the following.
다음으로, 시험예를 나타낸다. 시험예 1 에 있어서의 무처리란, 화합물 A 를 산포하지 않았던 것을 의미한다. 또, 시험예 2 및 3 에 있어서의 무처리구란, 화합물 A 를 사용하지 않는 것 이외에는 처리구와 동일한 조작을 하는 구를 의미한다.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.
시험예 1Test Example 1
플라스틱 포트에 토양을 채우고, 거기에 오이 (품종 ; 사가미한지로) 를 파종하고, 온실 내에서 19 일간 재배하였다. 폴리옥시에틸렌알킬에테르술페이트암모늄염 및 습식 실리카의 혼합물 (중량비 1 : 1) 35 부와, 화합물 A 20 부와, 물 45 부를 충분히 혼합하였다. 얻어진 혼합물을 물로 희석시켜, 화합물 A 를 500 ppm 함유하는 희석액을 조제하였다. 그 희석액을 그 오이 엽면에 충분히 부착되도록 산포하였다. 산포 후 식물을 풍건시키고, 1 일 후에 오이와 병균 (Pseudoperonospora cubensis) 유주자 (遊走子) 의 수 현탁액을 분무 접종하였다. 접종 후, 23 ℃, 다습하에 1 일간 두고, 계속해서 낮 동안 24 ℃, 밤 동안 20 ℃ 의 온실에서 6 일간 재배한 후, 병반 면적을 조사하였다. 그 결과, 화합물 A 를 처리한 오이에 있어서의 병반 면적은, 무처리의 오이에 있어서의 병반 면적의 30 % 이하였다.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.
시험예 2Test Example 2
화합물 A 를 소정 농도 함유하는 디메틸술폭사이드 용액 1 ㎖ 를 타이터 플레이트 (96 웰) 의 웰에 분주한 후, 박류 회색 역병균 (Phytophthora capsici) 의 유주자를 함유하는 감자 탕약 액체 배지를 150 ㎕ 분주하고, 화합물 A 가 최종 농도 100 ppm 이 되도록 조제하여, 처리구로 하였다. 또, 다른 웰에 무처리구를 조제하였다. 이 플레이트를 3 일간, 27 ℃ 에서 배양하여 박류 회색 역병균을 증식시킨 후, 타이터 플레이트의 각 웰의 600 ㎚ 의 흡광도를 측정하고, 박류 회색 역병균의 생육도로 하였다. 그 생육도를 기초로, 「식 1」을 사용하여 효력을 산출하였다.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".
「식 1」「Equation 1」
효력 (%) = 100 × (X ― Y)/X Effect (%) = 100 × (X-Y)/X
X : 무처리구의 균의 생육도 X: Growth degree of bacteria in the untreated area
Y : 처리구의 균의 생육도 Y: Growth degree of bacteria in the treated area
그 결과, 효력은 60 % 였다.As a result, the effect was 60%.
시험예 3Test Example 3
화합물 A 를 소정 농도 함유하는 디메틸술폭사이드 용액 1 ㎕ 를 타이터 플레이트 (96 웰) 의 웰에 분주한 후, 입고 병균 (Pythium ultimum) 의 균사 단편을 함유하는 차펙 배지를 150 ㎕ 분주하고, 화합물 A 가 최종 농도 100 ppm 이 되도록 조제하여, 처리구로 하였다. 또, 다른 웰에 무처리구를 조제하였다. 이 플레이트를 5 일간, 23 ℃ 에서 배양하여 입고 병균을 증식시킨 후, 타이터 플레이트의 각 웰의 600 ㎚ 의 흡광도를 측정하고, 입고 병균의 생육도로 하였다. 그 생육도를 기초로, 「식 1」을 사용하여 효력을 산출하였다. 그 결과, 효력은 73 % 였다.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%.
비교 시험예 1Comparative Test Example 1
화합물 A 대신에 화합물 B 를 사용하여, 시험예 1 에 따라서 시험을 실시하였다. 그 결과, 화합물 B 를 처리한 오이에 있어서의 병반 면적은, 무처리의 오이에 있어서의 병반 면적의 75 % 이상이었다.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.
비교 시험예 2Comparative Test Example 2
화합물 A 대신에 화합물 B 를 사용하여, 시험예 2 에 따라서 시험을 실시하였다. 그 결과, 효력은 26 % 였다.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%.
비교 시험예 3Comparative Test Example 3
화합물 A 대신에 화합물 B 를 사용하여, 시험예 3 에 따라서 시험을 실시하였다. 그 결과, 효력은 5 % 였다.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%.
산업상 이용가능성Industrial applicability
화합물 A 는, 식물 병해에 대하여 우수한 방제 효과를 나타낸다.Compound A exhibits an excellent control effect against plant diseases.
Claims (3)
로 나타내는 화합물.Equation (A)
Compound represented by.
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