KR20210046651A - 벤조옥사졸 화합물 및 그 용도 - Google Patents
벤조옥사졸 화합물 및 그 용도 Download PDFInfo
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
본 출원은 2018년 8월 20일에 출원된 일본 특허출원 제2018-153853호에 대한 우선권 및 그 이익을 주장하는 것으로, 그 전체 내용은 참조함으로써 본 출원에 편입된다.
본 발명은 벤조옥사졸 화합물 및 그 용도에 관한 것이다.
종래, 식물 병해를 방제하기 위해 여러 가지의 화합물이 개발되어 있고, 실용에 제공되고 있다 (비특허문헌 1 참조). 특허문헌 1 에는, 살충제로서 식 (B)
[화학식 1]
로 나타내는 화합물 (이하, 화합물 B 라고 기재한다) 이 기재되어 있다.
The Pesticide Manual-17th edition (BCPC 간행) ISBN 978-1-901396-88-1
본 발명은, 식물 병해에 대하여 우수한 방제 효력을 갖는 화합물을 제공하는 것을 과제로 한다.
본 발명은, 이하와 같다.
〔1〕 식 (A)
[화학식 2]
로 나타내는 화합물 (이하, 화합물 A 로 기재한다).
〔2〕〔1〕에 기재된 화합물과, 불활성 담체를 함유하는 조성물.
〔3〕〔1〕에 기재된 화합물의 유효량을 식물 또는 토양에 처리하는 것에 의한, 식물 병해의 방제 방법.
본 발명에 의해, 식물 병해를 방제할 수 있다.
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.
본 발명의 조성물은, 화합물 A 를 통상적으로 0.0001 ∼ 95 중량% 함유한다.
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.
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.
계면 활성제로는, 예를 들어 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌알킬아릴에테르, 폴리에틸렌글리콜 지방산 에스테르 등의 비이온 계면 활성제, 및 알킬술폰산염, 알킬벤젠술폰산염, 알킬황산염 등의 음이온 계면 활성제를 들 수 있다.
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.
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.
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 sp.), 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), 회색 곰팡이병 (Botrytis cinerea) ; 무우 검은무늬병 (Alternaria brassicicola) ; 잔디의 달러 스폿병 (Sclerotinia homoeocarpa), 잔디의 브라운 패치병 및 라지 패치병 (Rhizoctonia solani) ; 그리고 바나나의 시가토카병 (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.
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.
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.
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.
본 발명의 조성물은, 밭, 무논, 잔디밭, 과수원 등의 농경지에 있어서의 식물 병해의 방제제로서 사용할 수 있다.
실시예
이하, 본 발명을 제조예, 및 시험예 등에 의해 더욱 상세하게 설명하는데, 본 발명은 이들 예에만 한정되는 것은 아니다.
먼저, 화합물 A 의 제조예를 나타낸다.
제 1 공정
미국 특허 제8426443호 명세서에 기재된 방법으로 제조한 2-아미노-4-(트리플루오로메탄술포닐)페놀 69.7 g, N,N-디이소프로필에틸아민 37.3 g 및 테트라하이드로푸란 191 g 의 혼합물에, 질소 분위기하에서, 40 ℃ 에서 피리딘-2-카르보닐클로라이드 42.2 g 및 톨루엔 206 g 의 혼합물을 적하하고, 40 ℃ 에서 3 시간 교반하였다. 얻어진 혼합물에 8 % 수산화나트륨 수용액 88.8 g 을 첨가하고, 5 ℃ 로 냉각시켰다. 얻어진 고체를 여과하고, 여과물을 물 및 톨루엔으로 순차적으로 세정하고, 감압하에서 건조시켜, 하기 식으로 나타내는 중간체 A 를 42.1 g 얻었다.
[화학식 3]
제 2 공정
질소 분위기하에서, 중간체 A 20.0 g, 자일렌 100 g 및 p-톨루엔술폰산 일수화물 27.0 g 의 혼합물을 환류하에서, 딘스타크 장치를 사용하여 생성된 물을 계외로 제거하면서 6 시간 교반하였다. 얻어진 혼합물을 실온으로 냉각시키고, 20 % 탄산칼륨 수용액 39.9 g 에 첨가하여 분액하였다. 얻어진 유기층을 5 % 탄산칼륨 수용액으로 세정하고, 감압하에서 농축하였다. 얻어진 잔류물을 실리카 겔 칼럼 크로마토그래피에 부여하여, 화합물 A 를 10.0 g 얻었다.
화합물 A 의 1H-NMR 데이터를 이하에 나타낸다.
다음으로, 시험예를 나타낸다.
시험예 1
화합물 A 를 소정 농도 함유하는 디메틸술폭사이드 용액 1 ㎕ 를 타이터 플레이트 (96 웰) 의 웰에 분주한 후, 회색 곰팡이 병균 (Botrytis cinerea) 의 포자 현탁액을 함유하는 완전 배지를 150 ㎕ 분주하고, 화합물 A 가 최종 농도 100 ppm 이 되도록 조제하여, 처리구로 하였다. 또, 다른 웰에 무처리구를 조제하였다. 이 플레이트를 3 일간, 18 ℃ 에서 배양하여 회색 곰팡이 병균을 증식시킨 후, 타이터 플레이트의 각 웰의 600 ㎚ 의 흡광도를 측정하고, 회색 곰팡이 병균의 생육도로 하였다. 그 생육도를 기초로, 「식 1」을 사용하여 효력을 산출하였다.
「식 1」
효력 (%) = 100 × (X ― Y)/X
X : 무처리구의 균의 생육도
Y : 처리구의 균의 생육도
무처리구란, 화합물 A 를 사용하지 않은 것 이외에는 처리구와 동일한 조작을 하는 구를 의미한다.
그 결과, 효력은 60 % 였다.
비교 시험예 1
화합물 A 대신에 화합물 B 를 사용하여, 시험예 1 에 따라서 시험을 실시하였다. 그 결과, 효력은 0 % 였다.
산업상 이용가능성
화합물 A 는, 식물 병해에 대하여 우수한 방제 효과를 나타낸다.
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