KR20200129141A - 살진균제로서의 피콜린아미드 - Google Patents
살진균제로서의 피콜린아미드 Download PDFInfo
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- KR20200129141A KR20200129141A KR1020207028745A KR20207028745A KR20200129141A KR 20200129141 A KR20200129141 A KR 20200129141A KR 1020207028745 A KR1020207028745 A KR 1020207028745A KR 20207028745 A KR20207028745 A KR 20207028745A KR 20200129141 A KR20200129141 A KR 20200129141A
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- Prior art keywords
- hydrogen
- compound
- alkyl
- optionally substituted
- wheat
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- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/04—Carbamic acid halides
-
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Abstract
본 발명은 화학식 I의 피콜린아미드 및 살진균제로서의 그의 용도에 관한 것이다.
[화학식 I]
[화학식 I]
Description
관련 출원에 대한 상호 참조
본 출원은 2018년 3월 8일자로 출원된 미국 가특허출원 제62/640424호, 및 2018년 3월 8일자로 출원된 미국 가특허출원 제62/640434호의 이득에 대한 우선권을 주장하며, 이들의 개시 내용은 전체적으로 본원에 참고로 포함된다.
살진균제는, 농업 관련 진균에 의해 야기되는 손상에 대해 식물을 보호 및/또는 치유하는 역할을 하는, 천연 또는 합성 유래의 화합물이다. 일반적으로, 어떠한 단일 살진균제도 모든 상황에서 유용하지는 않다. 결과적으로, 더 우수한 성능을 가질 수 있고, 사용이 더 용이하며, 비용이 덜 드는 살진균제를 생산하기 위한 연구가 진행 중이다.
본 발명은 피콜린아미드 및 살진균제로서의 그의 용도에 관한 것이다. 본 발명의 화합물은 자낭균류, 담자균류, 불완전균류 및 난균류에 대한 보호를 제공할 수 있다.
본 발명의 일 실시 형태는 하기 화학식 I의 화합물을 포함할 수 있다:
[화학식 I]
(여기서,
X는 수소 또는 C(O)R4이고;
Y는 수소 또는 C(O)R4이고;
Z는 N 또는 N+→O-이고 W는 O 또는 S이고;
R1은 수소 또는 알킬이며, 이는 0개, 1개 또는 다수개의 R7로 치환되고;
R2는 메틸이고;
R3은 알킬, 아릴 또는 헤테로아릴로부터 선택되며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R4는 알콕시 또는 벤질옥시로부터 선택되며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R5는 수소, 알콕시, 또는 할로로부터 선택되며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R6은 수소, -C(O)R8, 또는 -CH2OC(O)R8로부터 선택되고;
R7은 수소, 알킬, 아릴, 아실, 할로, 알케닐, 알키닐, 알콕시, 시아노, 또는 헤테로시클릴로부터 선택되며, 각각은 선택적으로 0개, 1개 또는 다수개의 R9로 치환되고;
R8은 알킬, 알콕시, 또는 아릴로부터 선택되며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R9는 수소, 알킬, 아릴, 아실, 할로, 알케닐, 알콕시, 또는 헤테로시클릴로부터 선택되고;
R10은 수소 또는 알킬로부터 선택되며, 각각은 0개, 1개 또는 다수개의 R7로 치환됨).
본 발명의 다른 실시 형태는 상기에 기재된 화합물 및 식물학상 허용가능한 담체 물질을 포함하는, 진균 공격을 방제 또는 예방하기 위한 살진균 조성물을 포함할 수 있다.
본 발명의 또 다른 실시 형태는 식물에 대한 진균 공격을 방제 또는 예방하는 방법을 포함할 수 있으며, 이 방법은 살진균 유효량의 상기에 기재된 화합물 중 하나 이상을 진균, 식물, 및 식물에 인접한 영역 중 적어도 하나에 적용하는 단계를 포함한다.
다음의 용어들은 그의 정의 내에 일반적인 "R"-기를 포함할 수 있으며, 예를 들어, "용어 알콕시는 -OR 치환체를 지칭한다"는 것이 당업자에게 이해될 것이다. 다음의 용어들에 대한 정의 내에는, 이러한 "R" 기가 예시를 위해 포함되며 화학식 I에 대한 치환을 제한하거나 그에 의해 제한되는 것으로 해석되어서는 안 되는 것으로 또한 이해된다.
용어 "알킬"은 메틸, 에틸, 프로필, 부틸, 이소프로필, 이소부틸, 3차 부틸, 펜틸, 헥실, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등을 포함하지만 이로 한정되지 않는 분지형, 비분지형, 또는 포화 환형 탄소 사슬을 지칭한다.
용어 "알케닐"은 에테닐, 프로페닐, 부테닐, 이소프로페닐, 이소부테닐, 시클로부테닐, 시클로펜테닐, 시클로헥세닐 등을 포함하지만 이로 한정되지 않는, 하나 이상의 이중 결합을 함유하는 분지형, 비분지형, 또는 환형 탄소 사슬을 지칭한다.
용어 "아릴" 및 "Ar"은 0개의 헤테로원자를 함유하는, 단환식 또는 이환식인, 임의의 방향족 고리를 지칭한다.
용어 "헤테로시클릴"은 하나 이상의 헤테로원자를 함유하는, 단환식 또는 이환식인, 임의의 방향족 또는 비-방향족 고리를 지칭한다.
용어 "알콕시"는 -OR 치환체를 지칭한다.
용어 "아실옥시"는 -OC(O)R 치환체를 지칭한다.
용어 "시아노"는 -C≡N 치환체를 지칭한다.
용어 "히드록실"은 -OH 치환체를 지칭한다.
용어 "아미노"는 -N(R)2 치환체를 지칭한다.
용어 "아릴알콕시"는 -O(CH2) n Ar을 지칭하며, 여기서, n은 목록 1, 2, 3, 4, 5, 또는 6으로부터 선택되는 정수이다.
용어 "할로알콕시"는 -OR-X 치환체를 지칭하며, 여기서, X는 Cl, F, Br, 또는 I, 또는 이들의 임의의 조합이다.
용어 "할로알킬"은 Cl, F, I, 또는 Br 또는 이들의 임의의 조합으로 치환된 알킬을 지칭한다.
용어 "할로겐" 또는 "할로"는 F, Cl, Br, 및 I로서 정의되는 하나 이상의 할로겐 원자를 지칭한다.
용어 "니트로"는 -NO2 치환체를 지칭한다.
용어 티오알킬은 -SR 치환체를 지칭한다.
본 개시 내용의 전반에 걸쳐, 화학식 I의 화합물에 대한 언급은 모든 입체이성질체, 예를 들어 부분입체이성질체, 거울상이성질체, 및 이들의 혼합물을 또한 포함하는 것으로 해석된다. 또 다른 실시 형태에서, 화학식 I은 그의 염 또는 수화물을 또한 포함하는 것으로 해석된다. 예시적인 염은 히드로클로라이드, 히드로브로마이드, 히드로요오다이드, 트리플루오로아세테이트, 및 트리플루오로메탄 술포네이트를 포함하지만 이로 한정되지 않는다.
달리 언급되지 않는다면, 화학 결합 및 변형 에너지의 규칙이 충족되고 생성물이 여전히 살진균 활성을 나타내는 한, 추가적인 치환이 허용가능하다는 것이 당업자에게 또한 이해된다.
본 발명의 또 다른 실시 형태는 토양, 식물, 식물의 부분, 잎(foliage) 및/또는 뿌리에 화학식 I의 화합물 또는 이 화합물을 포함하는 조성물을 적용하는 것을 포함하는, 식물병원성 유기체에 의한 공격에 대한 식물의 보호 또는 식물병원성 유기체에 의해 감염된 식물의 치료를 위한 화학식 I의 화합물의 용도이다.
추가적으로, 본 발명의 또 다른 실시 형태는 화학식 I의 화합물 및 식물학상 허용가능한 담체 물질을 포함하는, 식물병원성 유기체에 의한 공격에 대한 식물의 보호 및/또는 식물병원성 유기체에 의해 감염된 식물의 치료에 유용한 조성물이다.
본 발명의 화합물은 임의의 다양한 공지된 기술에 의해, 화합물로서 또는 화합물을 포함하는 제형으로서 적용될 수 있다. 예를 들어, 화합물은 식물의 상업적 가치를 손상시키지 않으면서 다양한 진균의 방제를 위해 식물의 뿌리 또는 잎에 적용될 수 있다. 본 물질은 임의의 일반적으로 사용되는 제형 유형의 형태로, 예를 들어 용액, 분진, 습윤성 분말, 유동성 농축물 또는 유화성 농축물로서 적용될 수 있다.
바람직하게는, 본 발명의 화합물은 화학식 I의 화합물 중 하나 이상과 식물학상 허용가능한 담체를 포함하는 제형의 형태로 적용된다. 농축 제형은 적용을 위해 물 또는 다른 액체 중에 분산될 수 있거나, 또는 제형은 분진-유사 또는 과립형일 수 있는데, 이는 이어서 추가의 처리 없이 적용될 수 있다. 제형은 농업 화학 기술분야에서 통상적인 절차에 따라 제조될 수 있다.
본 발명은 화합물 중 하나 이상이 전달을 위해 제형화되고 살진균제로서 사용될 수 있도록 하는 모든 비히클을 고려한다. 전형적으로, 제형은 수성 현탁액 또는 에멀젼으로서 적용된다. 그러한 현탁액 또는 에멀젼은 보통 습윤성 분말로 공지된 고체; 또는 보통 유화성 농축물, 수성 현탁액 또는 현탁 농축물로 공지된 액체인, 수용성, 수현탁성 또는 유화성 제형으로부터 생성될 수 있다. 용이하게 인지되는 바와 같이, 항진균제로서의 이들 화합물의 활성에 대한 유의한 방해 없이 원하는 효용성을 제공한다면, 이들 화합물이 첨가될 수 있는 임의의 물질이 사용될 수 있다.
압축되어 수분산성 과립을 형성할 수 있는 습윤성 분말은 화학식 I의 화합물 중 하나 이상, 불활성 담체 및 계면활성제의 친밀한 혼합물을 포함한다. 습윤성 분말 중 화합물의 농도는 습윤성 분말의 총 중량을 기준으로 약 10 중량% 내지 약 90 중량%, 더욱 바람직하게는 약 25 중량% 내지 약 75 중량%일 수 있다. 습윤성 분말 제형의 제조에서, 화합물은 임의의 미분된 고체, 예컨대 프로필라이트, 활석, 백악, 석고, 풀러 토(Fuller's earth), 벤토나이트, 아타풀자이트, 전분, 카세인, 글루텐, 몬모릴로나이트 점토, 규조토, 정제된 실리케이트 등과 함께 배합될 수 있다. 그러한 작업에서, 미분된 담체 및 계면활성제는 전형적으로 화합물(들)과 함께 블렌딩되고 밀링된다.
화학식 I의 화합물의 유화성 농축물은 농축물의 총 중량을 기준으로, 적합한 액체 중에, 편리한 농도, 예컨대 약 1 중량% 내지 약 50 중량%의 화합물을 포함할 수 있다. 화합물은 수혼화성 용매, 또는 수불혼화성 유기 용매와 유화제의 혼합물인 불활성 담체 중에 용해될 수 있다. 농축물은 물 및 오일로 희석되어 수중유 에멀젼 형태의 분무 혼합물을 형성할 수 있다. 유용한 유기 용매는 방향족, 특히 석유의 고비점 나프탈렌 및 올레핀 부분, 예컨대 중질 방향족 나프타를 포함한다. 다른 유기 용매, 예를 들어 테르펜 용매(로진 유도체 포함), 지방족 케톤, 예컨대 시클로헥사논, 및 복합 알코올, 예컨대 2-에톡시에탄올이 또한 사용될 수 있다.
본원에서 유리하게 사용될 수 있는 유화제는 당업자에 의해 용이하게 결정될 수 있으며, 다양한 비이온성, 음이온성, 양이온성 및 양쪽성 유화제, 또는 둘 이상의 유화제의 블렌드를 포함할 수 있다. 유화성 농축물을 제조하는 데 유용한 비이온성 유화제의 예는 폴리알킬렌 글리콜 에테르, 및 알킬 및 아릴 페놀, 지방족 알코올, 지방족 아민 또는 지방산과 에틸렌 옥시드, 프로필렌 옥시드와의 축합 생성물, 예컨대 에톡실화 알킬 페놀, 및 폴리올 또는 폴리옥시알킬렌으로 가용화된 카르복실산 에스테르를 포함한다. 양이온성 유화제는 4차 암모늄 화합물 및 지방 아민 염을 포함한다. 음이온성 유화제는 알킬아릴 술폰산의 유용성(oilsoluble) 염(예를 들어, 칼슘), 황산화 폴리글리콜 에테르의 유용성 염 및 인산화 폴리글리콜 에테르의 적절한 염을 포함한다.
본 발명의 화합물의 유화성 농축물을 제조하는 데 사용될 수 있는 대표적인 유기 액체는 방향족 액체, 예컨대 자일렌, 프로필 벤젠 분획; 또는 혼합 나프탈렌 분획, 미네랄 오일, 치환된 방향족 유기 액체, 예컨대 디옥틸 프탈레이트; 케로센; 다양한 지방산의 디알킬 아미드, 특히 지방 글리콜 및 글리콜 유도체의 디메틸 아미드, 예컨대 디에틸렌 글리콜의 n-부틸 에테르, 에틸 에테르 또는 메틸 에테르, 트리에틸렌 글리콜의 메틸 에테르, 석유 분획 또는 탄화수소, 예컨대 미네랄 오일, 방향족 용매, 파라핀계 오일 등; 식물성 오일, 예컨대 대두유, 평지씨유, 올리브유, 피마자유, 해바라기씨유, 코코넛유, 옥수수유, 면실유, 아마씨유, 팜유, 땅콩유, 홍화유, 참깨유, 동유 등; 상기 식물성 오일의 에스테르 등이다. 둘 이상의 유기 액체의 혼합물이 또한 유화성 농축물의 제조에 사용될 수 있다. 유기 액체는 자일렌 및 프로필벤젠 분획을 포함하며, 일부 경우에 자일렌이 가장 바람직하다. 표면-활성 분산제는 전형적으로 화합물 중 하나 이상과 분산제의 합계 중량을 기준으로 0.1 내지 20 중량%의 양으로 액체 제형에 사용된다. 제형은 다른 상용성 첨가제, 예를 들어 식물 성장 조절제 및 농업에서 사용되는 다른 생물학적 활성 화합물을 또한 함유할 수 있다.
수성 현탁액은 수성 현탁액의 총 중량을 기준으로 약 1 내지 약 50 중량% 범위의 농도로 수성 비히클 중에 분산된 화학식 I의 하나 이상의 수불용성 화합물의 현탁액을 포함한다. 현탁액은 화합물 중 하나 이상을 미세하게 분쇄하고, 분쇄된 물질을 물 및 상기 논의된 것과 동일한 유형으로부터 선택된 계면활성제로 구성된 비히클 중에 격렬하게 혼합함으로써 제조된다. 수성 비히클의 밀도 및 점도를 증가시키기 위해 다른 성분, 예컨대 무기 염 및 합성 또는 천연 검이 또한 첨가될 수 있다.
또한, 화학식 I의 화합물은 토양에 적용하기에 특히 유용한 과립형 제형으로서 적용될 수 있다. 과립형 제형은 일반적으로, 조분된(coarsely divided) 불활성 물질, 예컨대 아타풀자이트, 벤토나이트, 규조토, 점토 또는 유사한 저렴한 물질로 전적으로 또는 대부분 이루어지는 불활성 담체 중에 분산된, 과립형 제형의 총 중량을 기준으로 약 0.5 내지 약 10 중량%의 화합물(들)을 함유한다. 그러한 제형은 통상적으로 화합물을 적합한 용매에 용해시키고, 이를 약 0.5 내지 약 3 mm 범위의 적절한 입자 크기로 예비형성된 과립형 담체에 적용함으로써 제조된다. 적합한 용매는 화합물이 실질적으로 또는 완전히 용해가능한 용매이다. 그러한 제형은 담체 및 화합물 및 용매의 도우 또는 페이스트를 제조하고, 분쇄 및 건조시켜 원하는 과립형 입자를 수득함으로써 제조될 수 있다.
화학식 I의 화합물을 함유하는 분진은 분말화된 형태의 화합물 중 하나 이상을, 예를 들어 카올린 점토, 분쇄된 화산암 등과 같은 적합한 분진성 농업용 담체와 친밀하게 혼합함으로써 제조될 수 있다. 분진은 적합하게는 분진의 총 중량을 기준으로 약 1 내지 약 10 중량%의 화합물을 함유할 수 있다.
제형은 표적 작물 및 유기체에 대한 화합물의 침착, 습윤화 및 침투를 향상시키기 위한 보조 계면활성제를 추가로 함유할 수 있다. 이러한 보조 계면활성제는 선택적으로 제형의 성분으로서 또는 탱크 믹스로서 사용될 수 있다. 보조 계면활성제의 양은 물의 분무-부피를 기준으로 전형적으로 0.01 내지 1.0 부피%, 바람직하게는 0.05 내지 0.5 부피%로 달라질 것이다. 적합한 보조 계면활성제는 에톡실화 노닐 페놀, 에톡실화 합성 또는 천연 알코올, 에스테르 또는 술포숙신산의 염, 에톡실화 유기실리콘, 에톡실화 지방 아민, 계면활성제와 미네랄 오일 또는 식물성 오일, 작물 오일 농축물과의 블렌드(미네랄 오일(85%) + 유화제(15%)); 노닐페놀 에톡실레이트; 벤질코코알킬디메틸 4차 암모늄 염; 석유 탄화수소, 알킬 에스테르, 유기 산 및 음이온성 계면활성제의 블렌드; C9 - C11 알킬폴리글리코시드; 인산화 알코올 에톡실레이트; 천연 1차 알코올(C12 - C16) 에톡실레이트; 디-sec-부틸페놀 EO-PO 블록 공중합체; 폴리실록산-메틸 캡(cap); 노닐페놀 에톡실레이트 + 우레아 암모늄 니트레이트; 유화된 메틸화 종자 오일; 트리데실 알코올(합성) 에톡실레이트(8EO); 탤로우 아민 에톡실레이트(15 EO); PEG(400) 디올레에이트-99를 포함하지만 이로 한정되지 않는다. 제형은 또한 미국 특허 출원 제11/495,228호에 개시된 것과 같은 수중유 에멀젼을 포함할 수 있으며, 이의 개시내용은 명백하게 본원에 참고로 포함된다.
제형은 선택적으로 다른 농약 화합물을 함유하는 조합물을 포함할 수 있다. 그러한 추가적인 농약 화합물은, 적용을 위해 선택된 매질 중에서 본 발명의 화합물과 상용성이며 본 발명의 화합물의 활성에 길항성이 아닌, 살진균제, 살충제, 제초제, 살선충제, 살진드기제, 살절지동물제, 살균제 또는 이들의 조합일 수 있다. 따라서, 그러한 실시 형태에서, 다른 농약 화합물이 동일하거나 상이한 농약 용도를 위한 보충 독성물로서 사용된다. 조합물 중 화학식 I의 화합물 및 농약 화합물은 일반적으로 1:100 내지 100:1의 중량비로 존재할 수 있다.
본 발명의 화합물은 또한 다른 살진균제와 조합되어 그의 살진균 혼합물 및 상승작용적 혼합물을 형성할 수 있다. 더 광범위한 다양한 바람직하지 않은 병해를 방제하기 하기 위해, 본 발명의 살진균 화합물은 보통 하나 이상의 다른 살진균제와 함께 적용된다. 다른 살진균제(들)와 함께 사용되는 경우에, 본원에서 청구된 화합물은 다른 살진균제(들)와 함께 제형화되거나, 다른 살진균제(들)와 함께 탱크-믹스되거나, 또는 다른 살진균제(들)와 함께 순차적으로 적용될 수 있다. 그러한 다른 살진균제는 2-(티오시아나토메틸티오)-벤조티아졸, 2-페닐페놀, 8-히드록시퀴놀린 술페이트, 아메톡트라딘, 아미노피리펜, 아미술브롬, 안티마이신, 암펠로미세스 퀴스쿠알리스(Ampelomyces quisqualis), 아자코나졸, 바실루스 서브틸리스(Bacillus subtilis), 바실루스 서브틸리스 균주 QST713, 베날락실, 베노밀, 벤티아발리카르브-이소프로필, 벤조빈디플루피르, 벤질아미노벤젠-술포네이트(BABS) 염, 비카르보네이트, 비페닐, 비스메르티아졸, 비테르타놀, 빅사펜, 블라스티시딘-S, 보락스, 보르도(Bordeaux) 혼합물, 보스칼리드, 브로무코나졸, 부피리메이트, 칼슘 폴리술피드, 캅타폴, 캅탄, 카르벤다짐, 카르복신, 카르프로파미드, 카르본, 클라자페논, 클로로네브, 클로로탈로닐, 클로졸리네이트, 코니오티리움 미니탄스(Coniothyrium minitans), 수산화구리, 옥탄산구리, 옥시염화구리, 황산구리, 황산구리(삼염기성), 산화제1구리, 시아조파미드, 시플루페나미드, 시목사닐, 시프로코나졸, 시프로디닐, 다조메트, 데바카르브, 디암모늄 에틸렌비스-(디티오카르바메이트), 디클로플루아니드, 디클로로펜, 디클로시메트, 디클로메진, 디클로란, 디에토펜카르브, 디페노코나졸, 디펜조쿼트 이온, 디플루메토림, 디메토모르프, 디목시스트로빈, 디니코나졸, 디니코나졸-M, 디노부톤, 디노캅, 디페닐아민, 디티아논, 도데모르프, 도데모르프 아세테이트, 도딘, 도딘 유리 염기, 에디펜포스, 에네스트로빈, 에네스트로부린, 에폭시코나졸, 에타복삼, 에톡시퀸, 에트리디아졸, 파목사돈, 페나미돈, 페나리몰, 펜부코나졸, 펜푸람, 펜헥사미드, 페녹사닐, 펜피클로닐, 펜프로피딘, 펜프로피모르프, 펜피라자민, 펜틴, 펜틴 아세테이트, 펜틴 히드록시드, 페르밤, 페림존, 플루아지남, 플루디옥소닐, 플루인다피르, 플루모르프, 플루오피콜리드, 플루오피람, 플루오로이미드, 플루옥사피프롤린, 플루옥사스트로빈, 플루퀸코나졸, 플루실라졸, 플루술파미드, 플루티아닐, 플루톨라닐, 플루트리아폴, 플룩사피록사드, 폴페트, 포름알데히드, 포세틸, 포세틸-알루미늄, 푸베리다졸, 푸랄락실, 푸라메트피르, 구아자틴, 구아자틴 아세테이트, GY-81, 헥사클로로벤젠, 헥사코나졸, 히멕사졸, 이마잘릴, 이마잘릴 술페이트, 이미벤코나졸, 이미녹타딘, 이미녹타딘 트리아세테이트, 이미녹타딘 트리스(알베실레이트), 인피르플룩삼, 요오도카르브, 이프코나졸, 이프펜피라졸론, 이프로벤포스, 이프로디온, 이프로발리카르브, 이소페타미드, 이소플루시프람, 이소프로티올란, 이소피라잠, 이소티아닐, 카수가마이신, 카수가마이신 히드로클로라이드 수화물, 크레속심-메틸, 라미나린, 만코퍼, 만코제브, 만디프로파미드, 마네브, 메페녹삼, 메파니피림, 메프로닐, 멥틸-디노캅, 염화제2수은, 산화제2수은, 염화제1수은, 메탈락실, 메탈락실-M, 메탐, 메탐-암모늄, 메탐-칼륨, 메탐-소듐, 메트코나졸, 메타술포카르브, 요오드화메틸, 메틸 이소티오시아네이트, 메티람, 메토미노스트로빈, 메트라페논, 밀디오마이신, 미클로부타닐, 나밤, 니트로탈-이소프로필, 누아리몰, 옥틸리논, 오푸레이스, 올레산(지방산), 오리사스트로빈, 옥사딕실, 옥사티아피프롤린, 옥신-구리, 옥스포코나졸 푸마레이트, 옥시카르복신, 페푸라조에이트, 펜코나졸, 펜시쿠론, 펜플루펜, 펜타클로로페놀, 펜타클로로페닐 라우레이트, 펜티오피라드, 페닐수은 아세테이트, 포스폰산, 프탈리드, 피콕시스트로빈, 폴리옥신 B, 폴리옥신, 폴리옥소림, 중탄산칼륨, 칼륨 히드록시퀴놀린 술페이트, 프로베나졸, 프로클로라즈, 프로시미돈, 프로파모카르브, 프로파모카르브 히드로클로라이드, 프로피코나졸, 프로피네브, 프로퀴나지드, 프로티오코나졸, 피디플루메토펜, 피라메토스트로빈, 피라옥시스트로빈, 피라클로스트로빈, 피라지플루미드, 피라조포스, 피리벤카르브, 피리부티카르브, 피리페녹스, 피리메타닐, 피리오페논, 피로퀼론, 퀴노클라민, 퀴녹시펜, 퀸토젠, 레이노우트리아 사칼리넨시스(Reynoutria sachalinensis) 추출물, 세닥산, 실티오팜, 시메코나졸, 소듐 2-페닐 페녹시드, 중탄산나트륨, 소듐 펜타클로로페녹시드, 스피록사민, 황, SYP-Z048, 타르 오일, 테부코나졸, 테부플로퀸, 테크나젠, 테트라코나졸, 티아벤다졸, 티플루자미드, 티오파네이트-메틸, 티람, 티아디닐, 톨클로포스-메틸, 톨릴플루아니드, 트리아디메폰, 트리아디메놀, 트리아족시드, 트리시클라졸, 트리데모르프, 트리플록시스트로빈, 트리플루미졸, 트리포린, 트리티코나졸, 발리다마이신, 발리페날레이트, 발리페날, 빈클로졸린, 지네브, 지람, 족사미드, 칸디다 올레오필라(Candida oleophila), 푸사리움 옥시스포룸(Fusarium oxysporum), 글리오클라디움(Gliocladium) 종, 플레비옵시스 기간테아(Phlebiopsis gigantea), 스트렙토미세스 그리세오비리디스(Streptomyces griseoviridis), 트리코더마(Trichoderma) 종, (RS)-N-(3,5-디클로로페닐)-2-(메톡시메틸)-숙신이미드, 1,2-디클로로프로판, 1,3-디클로로-1,1,3,3-테트라플루오로아세톤 수화물, 1-클로로-2,4-디니트로나프탈렌, 1-클로로-2-니트로프로판, 2-(2-헵타데실-2-이미다졸린-1-일)에탄올, 2,3-디히드로-5-페닐-1,4-디티-인 1,1,4,4-테트라옥시드, 2-메톡시에틸수은 아세테이트, 2-메톡시에틸수은 클로라이드, 2-메톡시에틸수은 실리케이트, 3-(4-클로로페닐)-5-메틸로다닌, 4-(2-니트로프로프-1-에닐)페닐 티오시아네이트, 암프로필포스, 아닐라진, 아지티람, 바륨 폴리술피드, Bayer 32394, 베노다닐, 벤퀴녹스, 벤탈루론, 벤자마크릴; 벤자마크릴-이소부틸, 벤자모르프, 비나파크릴, 비스(메틸수은) 술페이트, 비스(트리부틸주석) 옥시드, 부티오베이트, 카드뮴 칼슘 구리 아연 크로메이트 술페이트, 카르바모르프, CECA, 클로벤티아존, 클로라니포르메탄, 클로르페나졸, 클로르퀴녹스, 클림바졸, 구리 비스(3-페닐살리실레이트), 구리 아연 크로메이트, 쿠목시스트로빈, 쿠프라네브, 제2구리 히드라지늄 술페이트, 쿠프로밤, 시클라푸라미드, 시펜다졸, 시프로푸람, 데카펜틴, 디클로벤티아족스, 디클론, 디클로졸린, 디클로부트라졸, 디메티리몰, 디녹톤, 디노술폰, 디노테르본, 디피메티트론, 디피리티온, 디탈림포스, 도디신, 드라족솔론, EBP, 에녹사스트로빈, ESBP, 에타코나졸, 에템, 에티림, 페나민스트로빈, 페나미노술프, 페나파닐, 페니트로판, 펜피콕사미드, 플로릴피콕사미드, 플루페녹시스트로빈, 플루오피모미드, 플루오트리마졸, 푸르카르바닐, 푸르코나졸, 푸르코나졸-시스, 푸르메시클록스, 푸로파네이트, 글리오딘, 그리세오풀빈, 할라크리네이트, Hercules 3944, 헥실티오포스, ICIA0858, 이프펜트리플루코나졸, 이프플루페노퀸, 이소팜포스, 이소발레디온, 만데스트로빈, 메베닐, 메카르빈지드, 메펜트리플루코나졸, 메타족솔론, 메트푸록삼, 메틸수은 디시안디아미드, 메트술포박스, 메틸테트라프롤, 밀네브, 뮤코염소산 무수물, 미클로졸린, N-3,5-디클로로페닐-숙신이미드, N-3-니트로페닐이타콘이미드, 나타마이신, N-에틸메르쿠리오-4-톨루엔술폰아닐리드, 니켈 비스(디메틸디티오카르바메이트), OCH, 페닐수은 디메틸디티오카르바메이트, 페닐수은 니트레이트, 포스디펜, 프로티오카르브; 프로티오카르브 히드로클로라이드, 피라카르볼리드, 피라프로포인, 피리다클로메틸, 피리디니트릴, 피리족사졸, 피록시클로르, 피록시푸르, 퀴나세톨; 퀴나세톨 술페이트, 퀴나자미드, 퀸코나졸, 퀴노푸멜린, 라벤자졸, 살리실아닐리드, SSF-109, 술트로펜, 테코람, 티아디플루오르, 티시오펜, 티오클로르펜핌, 티오파네이트, 티오퀴녹스, 티옥시미드, 트리아미포스, 트리아리몰, 트리아즈부틸, 트리클라미드, 트리클로피리카르브, 트리플루메조피림, 우르바시드, 자릴아미드, 및 이들의 임의의 조합을 포함할 수 있다.
추가적으로, 본원에 기재된 화합물은 적용을 위해 선택된 매질 중에서 본 발명의 화합물과 상용성이며 본 발명의 화합물의 활성에 길항성이 아닌 살충제, 살선충제, 살진드기제, 살절지동물제, 살균제 또는 이들의 조합을 포함하는 다른 농약과 조합되어 그의 농약 혼합물 및 상승작용적 혼합물을 형성할 수 있다. 더 광범위한 다양한 바람직하지 않은 병해충을 방제하기 하기 위해, 본 발명의 살진균 화합물은 하나 이상의 다른 농약과 함께 적용될 수 있다. 다른 농약과 함께 사용되는 경우에, 본원에서 청구된 화합물은 다른 농약(들)과 함께 제형화되거나, 다른 농약(들)과 함께 탱크-믹스되거나, 또는 다른 농약(들)과 함께 순차적으로 적용될 수 있다. 전형적인 살충제는 1,2-디클로로프로판, 아바멕틴, 아세페이트, 아세타미프리드, 아세티온, 아세토프롤, 아크리나트린, 아크릴로니트릴, 아시노나피르, 아피도피로펜, 알라니카르브, 알디카르브, 알독시카르브, 알드린, 알레트린, 알로사미딘, 알릭시카르브, 알파-시페르메트린, 알파-엑디손, 알파-엔도술판, 아미디티온, 아미노카르브, 아미톤, 아미톤 옥살레이트, 아미트라즈, 아나바신, 아티다티온, 아자디라크틴, 아자메티포스, 아진포스-에틸, 아진포스-메틸, 아조토에이트, 바륨 헥사플루오로실리케이트, 바르트린, 벤디오카르브, 벤푸라카르브, 벤술탑, 벤즈피리목산, 베타-시플루트린, 베타-시페르메트린, 비펜트린, 비오알레트린, 비오에타노메트린, 비오페르메트린, 비스트리플루론, 보락스, 붕산, 브로플라닐리드, 브롬펜빈포스, 브로모시클렌, 브로모-DDT, 브로모포스, 브로모포스-에틸, 부펜카르브, 부프로페진, 부타카르브, 부타티오포스, 부토카르복심, 부토네이트, 부톡시카르복심, 카두사포스, 비산칼슘, 칼슘 폴리술피드, 캄페클로르, 카르바놀레이트, 카르바릴, 카르보푸란, 이황화탄소, 사염화탄소, 카르보페노티온, 카르보술판, 카르탑, 카르탑 히드로클로라이드, 클로란트라닐리프롤, 클로르비시클렌, 클로르단, 클로르데콘, 클로르디메포름, 클로르디메포름 히드로클로라이드, 클로르에톡시포스, 클로르페나피르, 클로르펜빈포스, 클로르플루아주론, 클로르메포스, 클로로포름, 클로로피크린, 클로로프랄레트린, 클로르폭심, 클로르프라조포스, 클로르피리포스, 클로르피리포스-메틸, 클로르티오포스, 크로마페노지드, 시네린 I, 시네린 II, 시네린, 시스메트린, 클로에토카르브, 클로산텔, 클로티아니딘, 아세토아비산구리, 비산구리, 나프텐산구리, 올레산구리, 쿠마포스, 쿠미토에이트, 크로타미톤, 크로톡시포스, 크루포메이트, 크리올라이트, 시아노펜포스, 시아노포스, 시안토에이트, 시안트라닐리프롤, 시클라닐리프롤, 시클레트린, 시클로프로트린, 시플루트린, 시할로디아미드, 시할로트린, 시페르메트린, 시페노트린, 시로마진, 시티오에이트, DDT, 데카르보푸란, 델타메트린, 데메피온, 데메피온-O, 데메피온-S, 데메톤, 데메톤-메틸, 데메톤-O, 데메톤-O-메틸, 데메톤-S, 데메톤-S-메틸, 데메톤-S-메틸술폰, 디아펜티우론, 디알리포스, 규조토, 디아지논, 디캅톤, 디클로펜티온, 디클로르보스, 디클로로메조티아즈, 디크레실, 디크로토포스, 디시클라닐, 디엘드린, 디플루벤주론, 딜로르, 디메플루트린, 디메폭스, 디메탄, 디메토에이트, 디메트린, 디메틸빈포스, 디메틸란, 디넥스, 디넥스-디클렉신, 디노프로프, 디노삼, 디노테푸란, 디오페놀란, 디옥사벤조포스, 디옥사카르브, 디옥사티온, 디술포톤, 디티크로포스, d-리모넨, DNOC, DNOC-암모늄, DNOC-칼륨, DNOC-소듐, 도라멕틴, 엑디스테론, 에마멕틴, 에마멕틴 벤조에이트, EMPC, 엠펜트린, 엔도술판, 엔도티온, 엔드린, EPN, 에포페노난, 에프리노멕틴, 엡실론-메토플루트린, 엡실론-몸플루오로트린, 에스데팔레트린, 에스펜발레레이트, 에타포스, 에티오펜카르브, 에티온, 에티프롤, 에토에이트-메틸, 에토프로포스, 에틸 포르메이트, 에틸-DDD, 에틸렌 디브로마이드, 에틸렌 디클로라이드, 에틸렌 옥시드, 에토펜프록스, 에트림포스, EXD, 팜푸르, 페나미포스, 페나자플로르, 펜클로르포스, 페네타카르브, 펜플루트린, 페니트로티온, 페노부카르브, 페녹사크림, 페녹시카르브, 펜피리트린, 펜프로파트린, 펜술포티온, 펜티온, 펜티온-에틸, 펜발레레이트, 피프로닐, 플로메토퀸, 플로니카미드, 플루아자인돌리진, 플루벤디아미드, 플루코푸론, 플루시클록수론, 플루시트리네이트, 플루엔술폰, 플루페네림, 플루페녹수론, 플루펜프록스, 플루피프롤, 플루헥사폰, 플루피라디푸론, 플루피리민, 플루발리네이트, 플룩사메타미드, 포노포스, 포르메타네이트, 포르메타네이트 히드로클로라이드, 포르모티온, 포름파라네이트, 포름파라네이트 히드로클로라이드, 포스메틸란, 포스피레이트, 포스티에탄, 푸라티오카르브, 푸레트린, 감마-시할로트린, 감마-HCH, 할펜프록스, 할로페노지드, HCH, HEOD, 헵타클로르, 헵타플루트린, 헵테노포스, 헤테로포스, 헥사플루무론, HHDN, 히드라메틸논, 시안화수소, 히드로프렌, 히퀸카르브, 이미다클로프리드, 이미프로트린, 인독사카르브, 요오도메탄, IPSP, 이사조포스, 이소벤잔, 이소카르보포스, 이소시클로세람, 이소드린, 이소펜포스, 이소펜포스-메틸, 이소프로카르브, 이소프로티올란, 이소티오에이트, 이속사티온, 이베르멕틴, 자스몰린 I, 자스몰린 II, 조드펜포스, 유충 호르몬 I, 유충 호르몬 II, 유충 호르몬 III, 카파-비펜트린, 카파-테플루트린, 켈레반, 키노프렌, 람다-시할로트린, 비산납, 레피멕틴, 렙토포스, 린단, 리림포스, 루페누론, 리티다티온, 말라티온, 말로노벤, 마지독스, 메카르밤, 메카르폰, 메나존, 메페르플루트린, 메포스폴란, 염화제1수은, 메술펜포스, 메타플루미존, 메타크리포스, 메타미도포스, 메티다티온, 메티오카르브, 메토크로토포스, 메토밀, 메토프렌, 메톡시클로르, 메톡시페노지드, 메틸 브로마이드, 메틸 이소티오시아네이트, 메틸클로로포름, 메틸렌 클로라이드, 메토플루트린, 메톨카르브, 메톡사디아존, 메빈포스, 멕사카르베이트, 밀베멕틴, 밀베마이신 옥심, 미파폭스, 미렉스, 몰로술탑, 몸플루오로트린, 모노크로토포스, 모노메히포, 모노술탑, 모르포티온, 목시덱틴, 나프탈로포스, 날레드, 나프탈렌, 니코틴, 니플루리디드, 니텐피람, 니티아진, 니트릴라카르브, 노발루론, 노비플루무론, 오메토에이트, 옥사밀, 옥사조술필, 오시데메톤-메틸, 옥시데프로포스, 옥시디술포톤, 파라-디클로로벤젠, 파라티온, 파라티온-메틸, 펜플루론, 펜타클로로페놀, 페르메트린, 펜캅톤, 페노트린, 펜토에이트, 포레이트, 포살론, 포스폴란, 포스메트, 포스니클로르, 포스파미돈, 포스핀, 폭심, 폭심-메틸, 피리메타포스, 피리미카르브, 피리미포스-에틸, 피리미포스-메틸, 아비산칼륨, 티오시안산칼륨, pp'-DDT, 프랄레트린, 프레코센 I, 프레코센 II, 프레코센 III, 프리미도포스, 프로페노포스, 프로플루랄린, 프로마실, 프로메카르브, 프로파포스, 프로페탐포스, 프로폭수르, 프로티다티온, 프로티오포스, 프로토에이트, 프로트리펜부트, 피플루부미드, 피라클로포스, 피라플루프롤, 피라조포스, 피레스메트린, 피레트린 I, 피레트린 II, 피레트린, 피리다벤, 피리달릴, 피리다펜티온, 피리플루퀴나존, 피리미디펜, 피리미노스트로빈, 피리미테이트, 피리프롤, 피리프록시펜, 콰시아, 퀴날포스, 퀴날포스-메틸, 퀴노티온, 라폭사니드, 레스메트린, 로테논, 리아니아, 사바딜라, 쉬라단, 셀라멕틴, 실라플루오펜, 실리카 겔, 아비산나트륨, 플루오르화나트륨, 소듐 헥사플루오로실리케이트, 티오시안산나트륨, 소파미드, 스피네토람, 스피노사드, 스피로메시펜, 스피로피디온, 스피로테트라마트, 술코푸론, 술코푸론-소듐, 술플루라미드, 술포텝, 술폭사플로르, 술푸릴 플루오라이드, 술프로포스, 타우-플루발리네이트, 타짐카르브, TDE, 테부페노지드, 테부펜피라드, 테부피림포스, 테플루벤주론, 테플루트린, 테메포스, TEPP, 테랄레트린, 테르부포스, 테트라클로르안트라닐리프롤, 테트라클로로에탄, 테트라클로르빈포스, 테트라메트린, 테트라메틸플루트린, 테트라닐리프롤, 세타-시페르메트린, 티아클로프리드, 티아메톡삼, 티크로포스, 티오카르복심, 티오시클람, 티오시클람 옥살레이트, 티오디카르브, 티오파녹스, 티오메톤, 티오술탑, 티오술탑-디소듐, 티오술탑-모노소듐, 투린기엔신, 티옥사자펜, 톨펜피라드, 트랄로메트린, 트랜스플루트린, 트랜스페르메트린, 트리아라텐, 트리아자메이트, 트리아조포스, 트리클로르폰, 트리클로르메타포스-3, 트리클로로나트, 트리페노포스, 트리플루메조피림, 트리플루무론, 트리메타카르브, 트리프렌, 티클로피라조플로르, 바미도티온, 바닐리프롤, XMC, 자일릴카르브, 제타-시페르메트린, 졸라프로포스, 및 이들의 임의의 조합을 포함하지만 이로 한정되지 않는다.
추가적으로, 본원에 기재된 화합물은 적용을 위해 선택된 매질 중에서 본 발명의 화합물과 상용성이며 본 발명의 화합물의 활성에 길항성이 아닌 제초제와 조합되어 그의 농약 혼합물 및 상승작용적 혼합물을 형성할 수 있다. 광범위한 다양한 바람직하지 않은 식물을 방제하기 하기 위해, 본 발명의 살진균 화합물은 하나 이상의 제초제와 함께 적용될 수 있다. 제초제와 함께 사용되는 경우에, 본원에서 청구된 화합물은 제초제(들)와 함께 제형화되거나, 제초제(들)와 함께 탱크-믹스되거나, 또는 제초제(들)와 함께 순차적으로 적용될 수 있다. 전형적인 제초제는 4-CPA; 4-CPB; 4-CPP; 2,4-D; 3,4-DA; 2,4-DB; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; 아세토클로르, 아시플루오르펜, 아클로니펜, 아크롤레인, 알라클로르, 알리도클로르, 알록시딤, 알릴 알코올, 알로락, 아메트리디온, 아메트린, 아미부진, 아미카르바존, 아미도술푸론, 아미노시클로피라클로르, 아미노피랄리드, 아미프로포스-메틸, 아미트롤, 술팜산암모늄, 아닐로포스, 아니수론, 아술람, 아트라톤, 아트라진, 아자페니딘, 아짐술푸론, 아지프로트린, 바르반, BCPC, 베플루부타미드, 베플루부타미드-M, 베나졸린, 벤카르바존, 벤플루랄린, 벤푸레세이트, 벤술푸론, 벤술리드, 벤타존, 벤자독스, 벤즈펜디존, 벤지프람, 벤조비시클론, 벤조페납, 벤조플루오르, 벤조일프로프, 벤즈티아주론, 비시클로피론, 비페녹스, 빌라나포스, 비스피리박, 빅슬로존, 보락스, 브로마실, 브로모보닐, 브로모부티드, 브로모페녹심, 브로목시닐, 브롬피라존, 부타클로르, 부타페나실, 부타미포스, 부테나클로르, 부티다졸, 부티우론, 부트랄린, 부트록시딤, 부투론, 부틸레이트, 카코딜산, 카펜스트롤, 염소산칼슘, 칼슘 시안아미드, 캄벤디클로르, 카르바술람, 카르베타미드, 카르복사졸 클로르프로카르브, 카르펜트라존, CDEA, CEPC, 클로메톡시펜, 클로람벤, 클로라노크릴, 클로라지포프, 클로라진, 클로르브로무론, 클로르부팜, 클로레투론, 클로르페낙, 클로르펜프로프, 클로르플루라졸, 클로르플루레놀, 클로리다존, 클로리무론, 클로르니트로펜, 클로로폰, 클로로톨루론, 클로록수론, 클로록시닐, 클로르프로팜, 클로르술푸론, 클로르탈, 클로르티아미드, 시니돈-에틸, 신메틸린, 시노술푸론, 시스아닐리드, 클라시포스, 클레토딤, 클리오디네이트, 클로디나포프, 클로포프, 클로마존, 클로메프로프, 클로프로프, 클로프록시딤, 클로피랄리드, 클로란술람, CMA, 황산구리, CPMF, CPPC, 크레다진, 크레졸, 쿠밀루론, 시아나트린, 시아나진, 시클로에이트, 시클로피라닐, 시클로피리모레이트, 시클로술파무론, 시클록시딤, 시클루론, 시할로포프, 시페르쿼트, 시프라진, 시프라졸, 시프로미드, 다이무론, 달라폰, 다조메트, 델라클로르, 데스메디팜, 데스메트린, 디-알레이트, 디캄바, 디클로베닐, 디클로랄우레아, 디클로르메이트, 디클로르프로프, 디클로르프로프-P, 디클로포프, 디클로술람, 디에탐쿼트, 디에타틸, 디페노펜텐, 디페녹수론, 디펜조쿼트, 디플루페니칸, 디플루펜조피르, 디메푸론, 디메피페레이트, 디메타클로르, 디메타메트린, 디메테나미드, 디메테나미드-P, 디멕사노, 디미다존, 디니트라민, 디노페네이트, 디노프로프, 디노삼, 디노세브, 디노테르브, 디페나미드, 디프로페트린, 디쿼트, 디술, 디티오피르, 디우론, DMPA, DNOC, DSMA, EBEP, 에글리나진, 엔도탈, 에프로나즈, EPTC, 에르본, 에스프로카르브, 에탈플루랄린, 에타메트술푸론, 에티디무론, 에티올레이트, 에토푸메세이트, 에톡시펜, 에톡시술푸론, 에티노펜, 에트니프로미드, 에토벤자니드, EXD, 페나술람, 페노프로프, 페녹사프로프, 페녹사프로프-P, 페녹사술폰, 펜퀴노트리온, 펜테라콜, 펜티아프로프, 펜트라자미드, 페누론, 황산제1철, 플람프로프, 플람프로프-M, 플라자술푸론, 플로라술람, 플로르피록시펜, 플루아지포프, 플루아지포프-P, 플루아졸레이트, 플루카르바존, 플루세토술푸론, 플루클로랄린, 플루페나세트, 플루페니칸, 플루펜피르, 플루메트술람, 플루메진, 플루미클로락, 플루미옥사진, 플루미프로핀, 플루오메투론, 플루오로디펜, 플루오로글리코펜, 플루오로미딘, 플루오로니트로펜, 플루오티우론, 플루폭삼, 플루프로파실, 플루프로파네이트, 플루피르술푸론, 플루리돈, 플루로클로리돈, 플루록시피르, 플루르타몬, 플루티아세트, 포메사펜, 포람술푸론, 포사민, 푸릴옥시펜, 글루포시네이트, 글루포시네이트-P, 글리포세이트, 할록시펜, 할로사펜, 할로술푸론, 할록시딘, 할록시포프, 할록시포프-P, 헥사클로로아세톤, 헥사플루레이트, 헥사지논, 이마자메타벤즈, 이마자목스, 이마자픽, 이마자피르, 이마자퀸, 이마제타피르, 이마조술푸론, 인다노판, 인다지플람, 요오도보닐, 요오도메탄, 요오도술푸론, 이오펜술푸론, 이옥시닐, 이파진, 이프펜카르바존, 이프리미담, 이소카르바미드, 이소실, 이소메티오진, 이소노루론, 이소폴리네이트, 이소프로팔린, 이소프로투론, 이소우론, 이속사벤, 이속사클로르톨, 이속사플루톨, 이속사피리포프, 카르부틸레이트, 케토스피라독스, 란코트리온, 락토펜, 레나실, 리누론, MAA, MAMA, MCPA, MCPA-티오에틸, MCPB, 메코프로프, 메코프로프-P, 메디노테르브, 메페나세트, 메플루이디드, 메소프라진, 메소술푸론, 메소트리온, 메탐, 메타미포프, 메타미트론, 메타자클로르, 메타조술푸론, 메트플루라존, 메타벤즈티아주론, 메탈프로팔린, 메타졸, 메티오벤카르브, 메티오졸린, 메티우론, 메토메톤, 메토프로트린, 메틸 브로마이드, 메틸 이소티오시아네이트, 메틸딤론, 메토벤주론, 메토브로무론, 메톨라클로르, 메토술람, 메톡수론, 메트리부진, 메트술푸론, 몰리네이트, 모날리드, 모니소우론, 모노클로로아세트산, 모노리누론, 모누론, 모르팜쿼트, MSMA, 나프로아닐리드, 나프로파미드, 나프로파미드-M, 나프탈람, 네부론, 니코술푸론, 니피라클로펜, 니트랄린, 니트로펜, 니트로플루오르펜, 노르플루라존, 노루론, OCH, 오르벤카르브, 오르토-디클로로벤젠, 오르토술파무론, 오리잘린, 옥사디아르길, 옥사디아존, 옥사피라존, 옥사술푸론, 옥사지클로메폰, 옥시플루오르펜, 파라플루론, 파라쿼트, 페불레이트, 펠라르곤산, 펜디메탈린, 페녹스술람, 펜타클로로페놀, 펜타노클로르, 펜톡사존, 퍼플루이돈, 페톡사미드, 펜이소팜, 펜메디팜, 펜메디팜-에틸, 페노벤주론, 페닐수은 아세테이트, 피클로람, 피콜리나펜, 피녹사덴, 피페로포스, 아비산칼륨, 아지드화칼륨, 시안산칼륨, 프레틸라클로르, 프리미술푸론, 프로시아진, 프로디아민, 프로플루아졸, 프로플루랄린, 프로폭시딤, 프로글리나진, 프로메톤, 프로메트린, 프로파클로르, 프로파닐, 프로파퀴자포프, 프로파진, 프로팜, 프로피소클로르, 프로폭시카르바존, 프로피리술푸론, 프로피자미드, 프로술팔린, 프로술포카르브, 프로술푸론, 프록산, 프리나클로르, 피다논, 피라클로닐, 피라플루펜, 피라술포톨, 피라졸리네이트, 피라조술푸론, 피라족시펜, 피리벤족심, 피리부티카르브, 피리클로르, 피리다폴, 피리데이트, 피리프탈리드, 피리미노박, 피리미술판, 피리티오박, 피록사술폰, 피록스술람, 퀸클로락, 퀸메락, 퀴노클라민, 퀴논아미드, 퀴잘로포프, 퀴잘로포프-P, 로데타닐, 림술푸론, 사플루페나실, S-메톨라클로르, 세부틸라진, 세크부메톤, 세톡시딤, 시두론, 시마진, 시메톤, 시메트린, SMA, 아비산나트륨, 아지드화나트륨, 염소산나트륨, 술코트리온, 술팔레이트, 술펜트라존, 술포메투론, 술포술푸론, 황산, 술글리카핀, 스웨프, TCA, 테부탐, 테부티우론, 테푸릴트리온, 템보트리온, 테프랄록시딤, 테르바실, 테르부카르브, 테르부클로르, 테르부메톤, 테르부틸라진, 테르부트린, 테트라플루론, 테닐클로르, 티아자플루론, 티아조피르, 티디아지민, 티디아주론, 티엔카르바존-메틸, 티펜술푸론, 티오벤카르브, 티아페나실, 티오카르바질, 티오클로림, 톨피랄레이트, 토프라메존, 트랄콕시딤, 트리아파몬, 트리-알레이트, 트리아술푸론, 트리아지플람, 트리베누론, 트리캄바, 트리클로피르, 트리디판, 트리에타진, 트리플록시술푸론, 트리플루디목사진, 트리플루랄린, 트리플루술푸론, 트리포프, 트리포프심, 트리히드록시트리아진, 트리메투론, 트리프로핀단, 트리탁, 트리토술푸론, 베르놀레이트, 및 자일라클로르를 포함하지만 이로 한정되지 않는다.
본 발명의 다른 실시 형태는 진균 공격을 방제 또는 예방하는 방법이다. 이 방법은 살진균 유효량의 화학식 I의 화합물 중 하나 이상을 토양, 식물, 뿌리, 잎, 또는 진균의 생육지에, 또는 침입이 예방되어야 하는 생육지에 적용하는 단계(예를 들어 곡류 또는 포도 식물에 적용하는 단계)를 포함한다. 본 화합물은 낮은 식물독성을 나타내면서 다양한 식물을 살진균 수준으로 처리하는 데 적합하다. 본 화합물은 보호제 및/또는 박멸제 방식 둘 모두에서 유용할 수 있다.
본 화합물은 특히 농업 용도에 유의한 살진균 효과를 갖는 것으로 밝혀졌다. 다수의 화합물이 농업 작물 및 원예 식물과 함께 사용하기에 특히 효과적이다.
전술된 진균에 대한 화합물의 효능은 살진균제로서의 화합물의 일반적 효용성을 확립하는 것으로 당업자에게 이해될 것이다.
본 화합물은 진균 병원체에 대해 광범위한 활성을 갖는다. 예시적인 병원체는 밀 잎마름병(wheat leaf blotch)(지모세프토리아 트리티시(Zymoseptoria tritici)), 밀 갈색녹병(wheat brown rust)(푹시니아 트리티시나(Puccinia triticina)), 밀 줄녹병(wheat stripe rust)(푹시니아 스트리이포르미스(Puccinia striiformis)), 사과 검은별무늬병(scab of apple)(벤투리아 이나에쿠알리스(Venturia inaequalis)), 포도덩굴 흰가루병(powdery mildew of grapevine)(운시눌라 네카토르(Uncinula necator)), 보리 구름무늬병(barley scald)(린코스포리움 세칼리스(Rhynchosporium secalis)), 도열병(blast of rice)(마그나포르테 그리세아(Magnaporthe grisea)), 대두 녹병(rust of soybean)(파코프소라 파키리지(Phakopsora pachyrhizi)), 밀 껍질마름병(glume blotch of wheat)(파라스타고노스포라 노도룸(Parastagonospora nodorum)), 밀 흰가루병(powdery mildew of wheat)(블루메리아 그라미니스 분화형 트리티시(Blumeria graminis f. sp.tritici)), 보리 흰가루병(Powdery Mildew of Barley)(블루메리아 그라미니스 분화형 호르데이(Blumeria graminis f. sp. hordei)), 박과 흰가루병(powdery mildew of cucurbits)(에리시페 시코라세아룸(Erysiphe cichoracearum)), 박과 탄저병(anthracnose of cucurbits)(글로메렐라 라게나리움(Glomerella lagenarium)), 비트 입반점병(leaf spot of beet)(세르코스포라 베티콜라(Cercospora beticola)), 토마토 겹무늬병(early blight of tomato)(알테르나리아 솔라니(Alternaria solani)), 및 보리 점무늬병(spot blotch of barley)(코클리오볼루스 사티부스(Cochliobolus sativus))의 유발제를 포함할 수 있지만 이로 한정되지 않는다. 적용될 활성 물질의 정확한 양은 적용되는 구체적 활성 물질뿐만 아니라 원하는 특정한 작용, 방제될 진균 종, 및 그의 성장 단계, 또한 화합물과 접촉될 식물의 부분 또는 다른 생성물에 따라 좌우된다. 따라서, 모든 화합물 및 그를 함유하는 제형이 유사한 농도에서 또는 동일한 진균 종에 대해 동등하게 효과적이지는 않을 수 있다.
본 화합물은 식물에서 병해-억제 및 식물학상 허용가능한 양으로 사용하기에 효과적이다. 용어 "병해-억제 및 식물학상 허용가능한 양"은 방제가 요구되는 식물 병해를 사멸시키거나 억제하기는 하지만 식물에 대해 유의하게 독성은 아닌 화합물의 양을 지칭한다. 이러한 양은 일반적으로 약 0.1 내지 약 1000 ppm(백만분율)일 것이며, 1 내지 500 ppm이 바람직하다. 필요한 화합물의 정확한 농도는 방제될 진균성 병해, 사용되는 제형의 유형, 적용 방법, 특정 식물 종, 기후 조건 등에 따라 달라진다. 적합한 적용률은 전형적으로 약 0.10 내지 약 4 파운드/에이커(약 0.01 내지 0.45 그램/제곱 미터, g/m2)의 범위이다.
본원의 교시를 이해하기 위해 숙련자에게 명백한 바와 같이, 본원에 주어진 임의의 범위 또는 바람직한 값은 추구하는 효과의 손실 없이 확장 또는 변경될 수 있다.
화학식 I의 화합물은 잘 알려진 화학적 절차를 사용하여 제조될 수 있다. 본 개시내용에서 구체적으로 언급되지 않은 중간체는 구매가능하거나, 화학 문헌에 개시된 경로에 의해 제조될 수 있거나, 표준 절차를 사용하여 시판 출발 물질로부터 용이하게 합성될 수 있다.
일반 반응식
하기 반응식은 화학식 I의 피콜린아미드 화합물을 생성하기 위한 접근법을 예시한다. 하기 기재 및 실시예는 예시적 목적으로 제공되며, 치환체 또는 치환 패턴의 관점에서 제한하는 것으로 간주되어서는 안 된다.
반응식 1, 단계 a 에 도시된 방법에 의해 화학식 1.2-Rac, 1.3-Rac 및 1.5-Rac, 1.6-Rac(여기서, R3은 앞서 정의된 바와 같음)의 라세미 혼합물을 제조할 수 있다.
[반응식 1]
단계 a 에 도시된 바와 같이, 화학식 1.0-Rac 및 1.4-Rac의 라세미 에폭시드 혼합물을 약 -78 oC 내지 55 oC의 온도에서, 테트라히드로푸란(THF) 또는 디에틸 에테르(Et2O)와 같은 극성 비양성자성 용매 중에서, 요오드화구리와 같은 금속 할라이드의 존재 하에, 아릴 마그네슘 할라이드와 같은 유기금속 친핵체와 반응시켜 화학식 1.2-Rac, 1.3-Rac 및 1.5-Rac, 1.6-Rac(여기서, R3은 앞서 정의된 바와 같음)의 라세미 혼합물을 제공한다.
화학식 1.2-Rac, 1.3-Rac 및 1.5-Rac, 1.6-Rac(여기서, R3은 앞서 정의된 바와 같음)의 라세미 혼합물을, 문헌[Akita (Tetrahedron: Asymmetry 2009, 20, 1286-1294)]에 기재되고 반응식 2, 단계 a 및 b 에 약술된 리파제-촉매된 동적 분해(lipase-catalyzed kinetic resolution)를 사용하여 그의 개별 거울상이성질체로 분리할 수 있다.
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화학식 1.2-Rac, 1.3-Rac 및 1.5-Rac, 1.6-Rac(여기서, R3은 앞서 정의된 바와 같음)의 라세미 혼합물을, 약 25 oC 내지 약 60 oC의 온도에서, 비닐 아세테이트와 같은 아세틸화 용매 중의 칸디다 안타르크티카(Candida antarctica) 리파제 B(CAL-B)로 처리하여, 화학식 1.2-Abs 및 1.5-Abs(여기서, R3은 본래 정의된 바와 같음)의 미반응 2차 알코올, 및 화학식 2.1-Abs 및 2.3-Abs(여기서, R3은 본래 정의된 바와 같음)의 아세틸화 화합물을 제공한다. 이 혼합물을, 헥산-에틸 아세테이트 혼합물을 이동상으로 사용하는 실리카 겔 크로마토그래피를 통해 정제하여, 화학식 1.2-Abs, 1.5-Abs, 2.1-Abs 및 2.3-Abs(여기서, R3은 본래 정의된 바와 같음)의 분해된 2차 알코올 및 아세테이트를 높은 거울상이성질체 과잉률로 얻을 수 있다. 1.2-Rac, 1.3-Rac, 1.5-Rac 및 1.6-Rac(여기서, R3은 본래 정의된 바와 같음)의 2차 알코올의 리파제 인식은 2차 알코올의 동적 분해에 대한 경험 법칙과 유사하다(문헌[Bornscheuer and Kazlauskus, Hydrolases in Organic Synthesis; Wiley-VCH, 2006]). 화학식 2.1-Abs 및 2.3-Abs(여기서, R3은 본래 정의된 바와 같음)의 아세테이트를, 약 25 oC 내지 약 60 oC의 온도에서, 메탄올과 같은 알코올성 용매 중에서 탄산칼륨과 같은 탄산염 염기로 처리하여, 화학식 2.2-Abs 및 2.4-Abs(여기서, R3은 본래 정의된 바와 같음)의 분해된 2차 알코올을 제공한다.
반응식 3, 단계 a 에 약술된 방법에 따라 화학식 3.2(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. 단계 a 에 도시된 바와 같이, 화학식 3.0(여기서, R2 및 R3은 본래 정의된 바와 같음)의 알코올을, 할로겐화 또는 극성 비양성자성 용매, 예컨대 (CH2Cl2) 또는 THF 중에서, 화학식 3.1(여기서, R1 및 R10은 본래 정의된 바와 같음)의 화합물, 커플링제, 예컨대 3-(에틸이미노메틸렌아미노)-N,N-디메틸프로판-1-아민 히드로클로라이드(EDC) 또는 중합체-지지된 카르보디이미드(PS-CDI), 및 촉매, 예컨대 N,N-디메틸피리딘-4-아민(DMAP)으로 처리하여 화학식 3.2(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을 제공할 수 있다.
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반응식 4, 단계 a 내지 d 에 약술된 방법에 따라 화학식 4.5(여기서, R1, R2, R3, R5, 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. 단계 a 에 도시된 바와 같이, 화학식 3.2(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을, 할로겐화 용매, 예컨대 CH2Cl2 중에서, 산으로, 예컨대 디옥산 중 염산(HCl)의 4 노르말(N) 용액으로 처리하여 화학식 4.1(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을 제공한다. 단계 c 에 도시된 바와 같이, 화학식 3.2(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을, 할로겐화 용매, 예컨대 CH2Cl2 중에서, 산, 예컨대 2,2,2-트리플루오로아세트산으로 처리하여 화학식 4.2(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. 단계 b 및 d 에 도시된 바와 같이, 화학식 4.1 및 4.2(여기서, R1, R2, R3, 및 R10은 본래 정의된 바와 같음)의 화합물을, 할로겐화 용매, 예컨대 CH2Cl2 중에서, 염기, 예컨대 디이소프로필에틸아민, 및 펩티드 커플링제, 예컨대 벤조트리아졸-1-일-옥시트리피롤리디노포스포늄 헥사플루오로포스페이트(PyBOP) 또는 O-(7-아자벤조-트리아졸-1-일)-N,N,N′,N′-테트라메틸우로늄 헥사플루오로포스페이트(HATU)의 존재 하에, 화학식 4.3(여기서, R5는 본래 정의된 바와 같음)의 화합물로 처리하여 화학식 4.5(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 제공할 수 있다.
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반응식 5, 단계 a 또는 b 에 약술된 방법에 따라 화학식 5.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. 단계 a 에 도시된 바와 같이, 화학식 4.5(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을, 약 25 oC 내지 약 50 oC의 온도에서, 아세톤과 같은 용매 중에서, 요오드화나트륨(NaI) 및 알칼리 탄산염 염기, 예컨대 탄산나트륨(Na2CO3) 또는 탄산칼륨(K2CO3)과 같은 시약을 사용하거나 사용하지 않고서, 적절한 알킬 할라이드로 처리할 수 있다. 또는, 대안적으로, 단계 b 에 도시된 바와 같이, CH2Cl2와 같은 비양성자성 용매 중에서, 아민 염기, 예컨대 피리딘, 트리에틸아민(NEt3), DMAP, 또는 이들의 혼합물의 존재 하에, 아실 할라이드 또는 무수물로 처리함으로써, 화학식 5.1(여기서, R1, R2, R3, R5, R6, 및 R10은 본래 정의된 바와 같음)의 화합물을 제공할 수 있다.
[반응식 5]
반응식 6, 단계 a 및 b 에 약술된 방법에 따라 화학식 6.1 및 6.2(여기서, R1, R2, R3, R5, R6, 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. 단계 a 에 도시된 바와 같이, 화학식 4.5(여기서, R1, R2, R3, R5, 및 R10은 본래 정의된 바와 같음)의 화합물을, 약 0℃ 내지 80℃의 온도에서, 선택적으로 아세토니트릴(CH3CN)과 같은 극성 비양성자성 용매 중에서, 오황화인과 같은 티오화제, 헥사메틸디실록산과 같은 첨가제로 처리하여 화학식 6.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 제공할 수 있다. 다음을 포함하지만 이로 한정되지 않는 다른 티오화제를 사용하여 화학식 6.1과 같은 화합물을 또한 제조할 수 있다는 것이 당업자에게 이해될 것이다: 황, 황화수소, 황화나트륨, 황화수소나트륨, 삼황화붕소, 비스(디에틸알루미늄)술피드, 황화암모늄, 로손 시약(Lawesson's reagent), 암모늄 O,O'-디에틸 디티오포스페이트, 로다닌, 또는 중합체 지지된 티오화 시약. 첨가제는 산화알루미늄(Al2O3); 무기 염기, 예컨대 탄산칼륨 및 중탄산나트륨; 유기 염기, 예컨대 트리에틸아민, 디에틸아닐린, 피리딘 및 모르폴린을 포함할 수 있지만 이로 한정되지 않는다. 선택적인 용매는 지방족, 지환족 또는 방향족 탄화수소, 예컨대 헥산, 시클로헥산 또는 톨루엔; 할로겐화 탄화수소, 예컨대 디클로로메탄, 1,2-디클로로에탄 및 클로로벤젠; 에테르, 예컨대 디에틸 에테르, 1,4-디옥산, THF 및 1,2-디메톡시에탄; 및 다른 극성 비양성자성 용매, 예컨대 피리딘 및 헥사메틸포스포르아미드(HMPA)를 포함할 수 있지만 이로 한정되지 않는다. 단계 b 에서는, 화학식 6.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을, 55℃의 온도에서, 아세톤과 같은 극성 비양성자성 용매 중에서, 요오드화나트륨(NaI) 및 알칼리 탄산염 염기, 예컨대 탄산나트륨(Na2CO3) 또는 탄산칼륨(K2CO3)과 같은 시약을 사용하거나 사용하지 않고서, 적절한 알킬 할라이드로 처리하거나, 또는 약 23℃의 온도에서, CH2Cl2와 같은 선택적인 비양성자성 용매 중에서, 아민 염기, 예컨대 피리딘, Et3N, DMAP, 또는 이들의 혼합물의 존재 하에, 아실 할라이드 또는 무수물로 처리하여, 화학식 6.2(여기서, R1, R2, R3, R5, R6, 및 R10은 본래 정의된 바와 같음)의 화합물을 제공할 수 있다.
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반응식 7, 단계 a 에 약술된 방법에 따라 화학식 7.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. a에 도시된 바와 같이, 화학식 4.5(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을, 약 0℃ 내지 50℃의 온도에서, CH2Cl2와 같은 극성 용매 중 m-클로로퍼벤조산(mCPBA)과 같은 산화 시약으로 처리하여 화학식 7.1(여기서, R1, R2, R3, R5 및 R10은 앞서 정의된 바와 같음)의 화합물을 제공할 수 있다. 다음을 포함하지만 이로 한정되지 않는 다른 산화 시약을 사용하여 화학식 7.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 또한 제조할 수 있다는 것이 당업자에게 이해될 것이다:
[반응식 7]
과산화수소, 과산화수소-우레아 복합체, 마그네슘 모노퍼옥시프탈레이트 육수화물(MMPP), 퍼옥시아세트산, 옥손, 과염소산나트륨 또는 디메틸 디옥시란.
반응식 8, 단계 a 에 약술된 방법에 따라 화학식 8.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 제조할 수 있다. a 에 도시된 바와 같이, 화학식 4.5(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을, 약 0℃ 내지 50℃의 온도에서, CH2Cl2와 같은 극성 용매 중에서, 피리딘과 같은 염기를 사용하여, 트리포스겐과 같은 이활성화(diactivated) 카르보닐 시약으로 처리하여 화학식 8.1(여기서, R1, R2, R3, R5 및 R10은 본래 정의된 바와 같음)의 화합물을 제공할 수 있다.
[반응식 8]
실시예
실시예 1A: 라세미 트레오-3-(2,4-디메틸페닐)부탄-2-올의 제조.
무수 Et2O (20 mL) 중 새로 활성화된 마그네슘 금속 셰이빙(1.14 g, 46.80 mmol)의 현탁액에 1-브로모-2,4-디메틸벤젠(8 g, 43.20 mmol)을 적가하였다. 혼합물을 약간의 환류(36℃)에서 5시간(hr) 동안 부드럽게 가열하였다. 생성된 진갈색 용액을, -20℃에서 Et2O(50 mL) 중에 현탁된 요오드화구리(I)(4.12 g, 21.61 mmol)가 담긴 플라스크에 주사기를 통해 첨가하였다. 진황색 현탁액을 -20℃에서 15분(min) 동안 교반하고 이어서 -50℃로 냉각시켰다. 라세미 트랜스-부텐 에폭시드(1.3 g, 18.01 mmol)를 천천히 적가한 후에 반응물을 실온으로 가온하고 하룻밤 교반하였다. 이어서, 혼합물을 0℃로 냉각시키고 포화 수성 염화암모늄(NH4Cl) 용액을 첨가하여 천천히 켄칭하였다. 혼합물을 셀라이트(Celite)의 패드를 통해 여과하고 패드를 에틸 아세테이트로 철저히 헹구었다. 유기 용액을 포화 NH4Cl 용액 및 염수로 세척하였다. 용액을 건조시키고(황산마그네슘(MgSO4)), 여과하고, 감압 하에 농축하였다. 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 40% 에틸 아세테이트/헥산 구배)를 통해 정제하여 라세미 트레오-3-(2,4-디메틸페닐)부탄-2-올을 황색 오일(813 mg, 25%)로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 7.06 (d, J = 8.5 Hz, 1H), 7.01 - 6.97 (m, 2H), 3.94 - 3.82 (m, 1H), 2.97 (p, J = 6.9 Hz, 1H), 2.29 (d, J = 7.7 Hz, 6H), 1.50 (d, J = 3.9 Hz, 1H), 1.28 (d, J = 7.0 Hz, 3H), 1.11 (d, J = 6.3 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 139.99, 135.49, 135.38, 131.31, 126.81, 126.18, 71.92, 41.42, 21.25, 20.87, 19.85, 16.06; EIMS m/z 178.
실시예 1B: 라세미 에리트로-3-(o-톨릴)부탄-2-올의 제조.
무수 Et2O(40 mL) 중 요오드화구리(I)(4.15 g, 21.60 mmol)의 -20℃ 현탁액에 2-메틸페닐마그네슘 브로마이드(Et2O 중 2.0 M, 22.5 mL, 43.20 mmol)를 천천히 적가하였다. 30 min 동안 교반한 후에, 주황색 현탁액을 -78℃로 냉각시키고, 라세미 시스-부텐 에폭시드(1.3 g, 18.01 mmol)를 천천히 첨가하였다. 드라이아이스 배스를 제거하였고 혼합물을 주위 온도로 천천히 가온하고 하룻밤 교반하였다. 얼음 배스로 혼합물을 0 oC로 냉각시키고 포화 수성 NH4Cl 용액의 적가에 의해 천천히 켄칭하였다. 혼합물을 실온으로 가온하고 셀라이트를 통해 여과한 후에, 패드를 에틸 아세테이트(EtOAc)로 헹구었다. 얻어진 여과액을 포화 수성 NH4Cl 용액 및 염수로 세척하였다. 이어서, 용액을 건조시키고(MgSO4), 감압 하에 농축하였다. 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 30% 에틸 아세테이트/헥산 구배)를 통해 정제하여 라세미 에리트로-3-(o-톨릴)부탄-2-올(2.05 g, 69%)을 황색 오일로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 7.34 - 7.01 (m, 4H), 3.92 (p, J = 6.3 Hz, 1H), 3.01 (p, J = 7.1 Hz, 1H), 2.36 (s, 3H), 1.47 (s, 1H), 1.28 (d, J = 6.1 Hz, 3H), 1.19 (d, J = 7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 142.14, 136.84, 130.61, 126.49, 125.81, 72.33, 42.62, 20.47, 19.93, 17.88; EIMS m/z 164.
실시예 1C: 라세미 트레오-3-페닐부탄-2-올의 제조.
에틸 에테르(18.0 mL) 중 요오드화구리(I)(1.86 g, 9.76 mmol)의 현탁액에, 질소 분위기 하에 0℃에서 페닐리튬(부틸 에테르 중 1.9 M, 10.3 mL, 19.53 mmol)을 적가하였다 0oC에서 1 hr 동안 교반한 후에, 라세미 트랜스-2,3-디메틸옥시란(0.64 g, 8.88 mmol)을 적가하고, 이어서 얼음 배스를 제거하고, 2 hr에 걸쳐 교반하면서 실온으로 가온하였다. 반응 혼합물을 물(20 mL)로 켄칭하고, 셀라이트의 패드를 통해 여과하고, 에틸 에테르(3 × 20 mL)로 추출하였다. 유기물을 상 분리기에 통과시키고 진공에서 농축하였다. 조(crude) 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 25% 아세톤/헥산 구배)를 통해 정제하여 라세미 트레오-3-페닐부탄-2-올(1.33 g, 8.85 mmol, 99%)을 주황색 오일로서 제공하였다: 1H NMR (400 MHz, CDCl3) δ 7.38 - 7.12 (m, 5H), 3.91 - 3.84 (m, 1H), 2.80 - 2.68 (m, 1H), 1.43 (s, 1H), 1.33 (d, J = 7.1 Hz, 3H), 1.09 (d, J = 6.3 Hz, 3H). 스펙트럼 데이터는 문헌[Tetrahedron 1981, 37, 709 - 713]에 보고된 것과 일치하였다.
실시예 2: (2S,3S)-3-(2,4-디메틸페닐)부탄-2-올 및 (2R,3R)-3-(2,4-디메틸페닐)부탄-2-올의 제조.
단계 1: (2S,3S)-3-(2,4-디메틸페닐)부탄-2-올 및 (2R,3R)-3-(2,4-디메틸페닐)부탄-2-일 아세테이트의 제조.
비닐 아세테이트(15 mL)에 용해된 라세미 트랜스-3-(2,4-디메틸페닐)부탄-2-올(800 mg, 4.49 mmol)의 용액이 담긴 바이알을 Novozym 435 리파제(CAL-B, 1.6 g, 4.49 mmol)의 비드로 충전하였다. 바이알을 오비탈 진탕기에 넣고 200 rpm에서 진탕하고 55℃에서 7.5 hr 동안 가열하였다. 반응물을 냉각시키고, EtOAc로 헹구어 프릿 디스크를 통해 여과하였다. 용출액을 감압 하에 농축하여 906 mg의 조 황색 오일을 제공하였다. 잔류물을, 플래시 컬럼 크로마토그래피(SiO2, 0 내지 20% 에틸 아세테이트/헥산 구배)를 통해 정제하여 (2R,3R)-3-(2,4-디메틸페닐)부탄-2-일 아세테이트(투명 오일, 466 mg, 47%), 이어서 (2S,3S)-3-(2,4-디메틸페닐)부탄-2-올(투명 황색 오일, 357 mg, 43%)을 제공하였다. 아세테이트: 1H NMR (500 MHz, CDCl3) δ 7.07 (d, J = 7.7 Hz, 1H), 7.01 - 6.97 (m, 2H), 5.08 (dq, J = 8.5, 6.3 Hz, 1H), 3.16 - 3.05 (m, 1H), 2.30 (s, 3H), 2.28 (s, 3H), 2.06 (s, 3H), 1.21 (d, J = 6.9 Hz, 3H), 1.06 (d, J = 6.3 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 170.80, 138.92, 135.56, 135.42, 131.22, 126.93, 126.33, 75.09, 39.48, 21.34, 20.89, 19.88, 18.34, 17.96; EIMS m/z 220. 알코올: 1H NMR (500 MHz, CDCl3) δ 7.06 (d, J = 8.5 Hz, 1H), 7.01 - 6.97 (m, 2H), 3.88 (tt, J = 9.2, 4.7 Hz, 1H), 2.97 (p, J = 6.9 Hz, 1H), 2.30 (s, 3H), 2.28 (s, 3H), 1.49 (d, J = 3.5 Hz, 1H), 1.28 (d, J = 7.0 Hz, 3H), 1.11 (d, J = 6.3 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 140.00, 135.49, 135.38, 131.31, 126.82, 126.18, 71.92, 41.43, 21.25, 20.87, 19.85, 16.07; EIMS m/z 178. 거울상이성질체 HPLC 분리(210 nm 파장)를 통한 분석에 의해, (2S,3S)-3-(2,4-디메틸페닐)부탄-2-올의 거울상이성질체 비는 96:4인 것으로 결정되었다.
단계 2: (2R,3R)-3-(2,4-디메틸페닐)부탄-2-올의 제조.
메탄올(4.2 mL)에 용해된 상기 제조된 (2R,3R)-3-(2,4-디메틸페닐)부탄-2-일 아세테이트(458 mg, 2.08 mmol)를 함유하는 용액에 탄산칼륨(431 mg, 3.12 mmol)을 첨가하였다. 혼합물을 주위 온도에서 1.5 hr 동안 교반하고, 이어서 2 hr 동안 50℃로 가열하였다. 반응물을 냉각시키고 감압 하에 농축하였다. 잔류물을 아세톤으로 희석하고, 소형 실리카 겔 플러그에 통과시켜, 패드를 아세톤으로 잘 세척하였다. 용매를 진공에서 농축하여 (2R,3R)-3-(2,4-디메틸페닐)부탄-2-올(332 mg, 90%)을 황색 오일로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 7.06 (d, J = 8.5 Hz, 1H), 7.01 - 6.97 (m, 2H), 3.88 (p, J = 6.3 Hz, 1H), 2.97 (p, J = 6.9 Hz, 1H), 2.30 (s, 3H), 2.28 (s, 3H), 1.49 (s, 1H), 1.28 (d, J = 7.0 Hz, 3H), 1.11 (d, J = 6.3 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 140.00, 135.49, 135.38, 131.31, 126.82, 126.18, 71.92, 41.43, 21.26, 20.87, 19.85, 16.07; EIMS m/z 178. 거울상이성질체 HPLC에 의한 분석을 통해, 알코올의 거울상이성질체 비는 7:93인 것으로 결정되었다.
실시예 3: (2S,3S)-3-페닐부탄-2-올 (tert-부톡시카르보닐)-L-알라니네이트의 제조.
메틸렌 클로라이드(7.7 mL)에 용해된 (2S,3S)-3-페닐부탄-2-올(0.23 g, 1.53 mmol)의 용액에 N-에틸-N'-(3-디메틸아미노프로필)카르보디이미드 히드로클로라이드(0.59 g, 3.06 mmol) 및 N,N-디메틸피리딘-4-아민(19 mg, 0.15 mmol)을 첨가하였다. 반응 혼합물을 질소로 퍼지하고, 16 hr에 걸쳐 교반하고, 이어서 진공에서 농축하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 20% 에틸 아세테이트/헥산 구배)를 통해 정제하여, (2S,3S)-3-페닐부탄-2-일 (tert-부톡시카르보닐)-L-알라니네이트(0.43 g, 1.34 mmol, 83% 수율)를 무색 오일로서 제공하였다: 1H NMR (400 MHz, CDCl3) δ 7.35 - 7.25 (m, 2H), 7.27 - 7.15 (m, 3H), 5.12 - 5.01 (m, 2H), 4.35 - 4.26 (m, 1H), 2.95 - 2.83 (m, 1H), 1.45 (s, 9H), 1.37 (d, J = 7.2 Hz, 3H), 1.29 (d, J = 7.1 Hz, 3H), 1.09 (d, J = 6.3 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 172.9, 155.0, 143.0, 128.5, 127.8, 126.7, 79.7, 76.1, 49.5, 45.1, 28.3, 18.9, 18.3, 17.5; IR (박막) 3355, 2978, 2934, 1711, 1495, 1452, 1366, 1161, 1087, 1065, 701 cm-1.
실시예 4: (2S,3S)-3-페닐부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트의 제조.
단계 1: (2S,3S)-3-페닐부탄-2-일-L-알라니네이트·히드로클로라이드의 제조.
니트(neat) (2S,3S)-3-페닐부탄-2-올 (tert-부톡시카르보닐)-L-알라니네이트(0.42 g, 1.31 mmol)에 질소 하에서 디옥산(4 M, 3.3 mL, 13.07 mmol)에 용해된 HCl의 용액을 적가하였다. 16 hr 동안 교반한 후에, 반응 혼합물을 진공에서 농축하여, 조 (2S,3S)-3-페닐부탄-2-일-L-알라니네이트·염화수소를 백색 고체로서 제공하였고, 이를 직접 다음 단계로 전달하였다: HRMS-ESI (m/z) [M+H]+ C13H20NO2에 대한 계산치, 222.1489; 실측치, 222.1485.
단계 2: (2S,3S)-3-페닐부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트의 제조.
메틸렌 클로라이드(6.5 mL)에 용해된 (2S,3S)-3-페닐부탄-2-일-L-알라니네이트·염화수소, 3-히드록시-4-메톡시피콜린산(0.24 g, 1.44 mmol), 및 (밴조트리아졸-1-일옥시)트리피롤리디노포스포늄 헥사플루오로포스페이트(0.75 g, 1.44 mmol)의 용액에 질소 하에서 N,N-디이소프로필에틸아민(0.75 mL, 4.31 mmol)을 적가하였다. 16 hr 동안 교반한 후에, 반응 혼합물을 진공에서 농축하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 45% 아세톤/헥산 구배)를 통해 정제하여, (2S,3S)-3-페닐부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트(0.46 g, 1.173 mmol, 90% 수율)를 무색 오일로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 12.16 (s, 1H), 8.50 (d, J = 8.0 Hz, 1H), 8.01 (d, J = 5.2 Hz, 1H), 7.32 - 7.27 (m, 2H), 7.24 - 7.16 (m, 3H), 6.88 (d, J = 5.2 Hz, 1H), 5.11 (dq, J = 7.7, 6.3 Hz, 1H), 4.77 - 4.67 (m, 1H), 3.95 (s, 3H), 2.97 - 2.87 (m, 1H), 1.54 (d, J = 7.2 Hz, 3H), 1.31 (d, J = 7.0 Hz, 3H), 1.13 (d, J = 6.3 Hz, 3H); IR (박막) 2978, 2937, 1733, 1647, 1527, 1451, 1262, 1147, 701 cm-1; HRMS-ESI (m/z) [M+H]+ C20H25N2O5에 대한 계산치, 373.1758; 실측치, 373.1752.
실시예 5A: (2S,3S)-3-페닐부탄-2-일 (3-아세톡시-4-메톡시피콜리노일)-L-알라니네이트의 제조.
피리딘(1.0 mL)에 용해된 (2S,3S)-3-페닐부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트(84 mg, 0.23 mmol)를 함유하는 용액에 질소 하에서 아세트산무수물(0.25 mL, 2.65 mmol)를 적가하였다. 30 min 동안 교반한 후에, 반응 혼합물을 진공에서 농축하고, 이어서 톨루엔(10 mL)과 공비시켰다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 40% 아세톤/헥산 구배)를 통해 정제하여, (2S,3S)-3-페닐부탄-2-일 (3-아세톡시-4-메톡시피콜리노일)-L-알라니네이트(90 mg, 0.21 mmol, 91% 수율)를 무색 오일로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 8.56 (s, 1H), 8.34 (d, J = 5.5 Hz, 1H), 7.32 - 7.27 (m, 2H), 7.24 - 7.16 (m, 3H), 7.01 (d, J = 5.5 Hz, 1H), 5.09 (dq, J = 7.7, 6.3 Hz, 1H), 4.77 - 4.67 (m, 1H), 3.91 (s, 3H), 2.96 - 2.86 (m, 1H), 2.41 (s, 3H), 1.49 (d, J = 7.2 Hz, 3H), 1.30 (d, J = 7.0 Hz, 3H), 1.10 (d, J = 6.3 Hz, 3H); IR (박막) 3377, 2980, 2938, 1770, 1732, 1674, 1507, 1310, 1198, 1174, 702 cm-1; HRMS-ESI (m/z) [M+H]+ C22H27N2O6에 대한 계산치, 415.1864; 실측치, 415.1859.
실시예 5B: (2S,3R)-3-(o-톨릴)부탄-2-일 (3-(아세톡시메톡시)-4-메톡시피콜리노일)-L-알라니네이트의 제조.
0.7 mL의 아세톤에 용해된 (2S,3R)-3-(o-톨릴)부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트를 함유하는 용액에 탄산칼륨(39 mg, 0.279 mmol)을 첨가하고 이어서 브로모메틸 아세테이트(27 μL, 0.279 mmol)를 첨가하였다. 용액을 50 oC에서 1.5 hr 동안 가열하였다. 반응 혼합물을 냉각시키고 진공에서 농축하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 80% 아세톤/헥산 구배)를 통해 정제하여, (2S,3R)-3-(o-톨릴)부탄-2-일 (3-(아세톡시메톡시)-4-메톡시피콜리노일)-L-알라니네이트(63 mg, 93% 수율)를 진한 오일로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 8.26 (d, J = 5.4 Hz, 1H), 8.22 (t, J = 7.4 Hz, 1H), 7.22 - 7.03 (m, 4H), 6.93 (d, J = 5.4 Hz, 1H), 5.73 (dd, J = 5.6, 1.8 Hz, 2H), 5.16 (dq, J = 8.1, 6.3 Hz, 1H), 4.58 - 4.51 (m, 1H), 3.90 (s, 3H), 3.31 - 3.22 (m, 1H), 2.37 (s, 3H), 2.06 (s, 3H), 1.31 (d, J = 6.2 Hz, 3H), 1.24 (d, J = 7.0 Hz, 3H), 1.03 (d, J = 7.2 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ 172.26, 170.26, 162.87, 160.25, 145.68, 143.94, 142.57, 141.57, 136.03, 130.21, 126.16, 125.94, 109.49, 89.57, 75.57, 56.16, 48.08, 39.48, 20.87, 19.84, 17.92, 17.77, 17.05; HRMS-ESI (m/z) [M+H]+ C24H30N2O7에 대한 계산치, 459.2126; 실측치, 459.2121.
실시예 5C: 4-메톡시-2-(((S)-1-옥소-1-(((2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일)옥시)프로판-2-일)카르바모일)피리딘-3-일 이소부티레이트의 제조.
CH2Cl2(2 mL) 중에 (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트(283.9 mg, 0.645 mmol) 및 N,N-디메틸피리딘-4-아민(15.75 mg, 0.129 mmol)을 함유하는 용액을 제조하였다. 이 용액에 트리에틸아민(0.180 mL, 1.289 mmol)을 첨가하고, 이어서 이소부티릴 클로라이드(0.102 mL, 0.967 mmol)를 첨가하였다. 생성된 투명한 반응물을 주위 온도에서 하룻밤 교반하였다. 반응물을 감압 하에 농축하여 N2의 스트림 하에서 주황색 오일을 제공하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 100% 에틸 아세테이트/헥산 구배)를 통해 정제하여 4-메톡시-2-(((S)-1-옥소-1-(((2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일)옥시)프로판-2-일)카르바모일)피리딘-3-일 이소부티레이트(252.3 mg, 0.494 mmol, 77 % 수율)를 황색 오일로서 제공하였다: 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J = 7.4 Hz, 1H), 8.34 (d, J = 5.4 Hz, 1H), 7.64 (dd, J = 8.0, 1.3 Hz, 1H), 7.54 - 7.47 (m, 1H), 7.44 (d, J = 7.8 Hz, 1H), 7.31 (t, J = 7.5 Hz, 1H), 6.99 (d, J = 5.4 Hz, 1H), 5.26 - 5.11 (m, 1H), 4.76 (p, J = 7.3 Hz, 1H), 3.89 (s, 3H), 3.34 (p, J = 6.6 Hz, 1H), 2.96 (hept, J = 7.0 Hz, 1H), 1.54 (d, J = 7.2 Hz, 3H), 1.36 (dd, J = 7.0, 1.3 Hz, 6H), 1.28 (d, J = 6.8 Hz, 3H), 1.10 (d, J = 6.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ -58.25; IR (박막) 3383, 2981, 1737, 1679, 1505, 1310, 1114, 1045, 732 cm-1; HRMS-ESI (m/z) [M+H]+ C25H30F3N2O6에 대한 계산치, 511.2050; 실측치, 511.2048.
실시예 6: (2S,3S)-3-(2,4-디메틸페닐)부탄-2-일 (3-아세톡시-4-메톡시피리딘-2-카르보노티오일)-L-알라니네이트의 제조.
단계 1: (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-히드록시-4-메톡시피리딘-2-카르보노티오일)-L-알라니네이트의 제조.
아세토니트릴(2.73 mL)에 용해된 (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트(120.1 mg, 0.273 mmol)를 함유하는 용액에 오황화인(121 mg, 0.545 mmol)을 첨가한 후에, 1,1,1,3,3,3-헥사메틸디실록산(291 μL, 1.363 mmol)을 한꺼번에 첨가하였다. 반응물을 30 min 동안 45℃로 가열하였다. 반응물을 냉각시키고, CH2Cl2(10 mL)로 희석하고, 포화 수성 NaHCO3(10 mL)의 첨가에 의해 켄칭하였다. 층을 분리하고 수성 층을 CH2Cl2(3 x 10 mL)로 추출하였다. 합한 유기층을 상 분리기에 통과시키고 황색 오일로 농축하였다. 조 물질을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 50% 아세톤/헥산 구배)를 통해 정제하여, (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-히드록시-4-메톡시피리딘-2-카르보노티오일)-L-알라니네이트(104.7 mg, 0.229 mmol, 84 % 수율)를 황색 반고체로서 제공하였다;1H NMR (400 MHz, CDCl3) δ 12.93 (s, 1H), 10.74 (d, J = 7.6 Hz, 1H), 8.00 (d, J = 5.1 Hz, 1H), 7.73 - 7.59 (m, 1H), 7.51 (t, J = 7.7 Hz, 1H), 7.43 (d, J = 7.8 Hz, 1H), 7.33 (t, J = 7.5 Hz, 1H), 6.89 (d, J = 5.1 Hz, 1H), 5.30 - 5.18 (m, 1H), 5.14 (p, J = 7.2 Hz, 1H), 3.96 (s, 3H), 3.37 (p, J = 6.8 Hz, 1H), 1.69 (dd, J = 7.2, 3.2 Hz, 3H), 1.30 (d, J = 6.8 Hz, 3H), 1.14 (d, J = 6.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ -58.23; IR (박막) 3087, 2984, 1737, 1513, 1484, 1311, 1151, 1118, 800, 771 cm-1; HRMS-ESI (m/z) [M+H]+ C21H24F3N2O4S에 대한 계산치, 457.1403; 실측치, 457.1399.
단계 2: (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-아세톡시-4-메톡시피리딘-2-카르보노티오일)-L-알라니네이트의 제조.
CH2Cl2(2 mL)에 용해된 (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-히드록시-4-메톡시피리딘-2-카르보노티오일)-L-알라니네이트(53.9 mg, 0.118 mmol) 및 N,N-디메틸피리딘-4-아민(2.89 mg, 0.024 mmol)을 함유하는 용액에 트리에틸아민(0.041 mL, 0.295 mmol)을 첨가하고, 이어서 아세틸 클로라이드(9.23 μL, 0.130 mmol)를 첨가하였다. 생성된 연주황색 반응물을 주위 온도에서 18 hr 동안 교반하였다. 반응물을 감압 하에 농축하여 N2의 스트림 하에서 주황색 오일을 제공하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 50% 아세톤/헥산 구배)를 통해 정제하여, (2S,3S)-3-(2-(트리플루오로메틸)페닐)부탄-2-일 (3-아세톡시-4-메톡시피리딘-2-카르보노티오일)-L-알라니네이트(51.7 mg, 0.104 mmol, 88% 수율)를 황색 오일로서 제공하였다: 1H NMR (400 MHz, CDCl3) δ 9.96 (d, J = 7.3 Hz, 1H), 8.34 (d, J = 5.5 Hz, 1H), 7.71 - 7.59 (m, 1H), 7.59 - 7.47 (m, 1H), 7.44 (d, J = 7.8 Hz, 1H), 7.39 - 7.28 (m, 1H), 7.00 (d, J = 5.5 Hz, 1H), 5.28 - 5.15 (m, 2H), 3.91 (s, 3H), 3.42 - 3.29 (m, 1H), 2.37 (s, 3H), 1.64 (d, J = 7.2 Hz, 3H), 1.30 (d, J = 6.8 Hz, 3H), 1.12 (d, J = 6.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ -58.23; HRMS-ESI (m/z) [M+H]+ C23H26F3N2O5S에 대한 계산치, 499.1509; 실측치, 499.1508.
실시예 7: 3-히드록시-4-메톡시-2-(((S)-1-옥소-1-(((2S,3S)-3-페닐부탄-2-일)옥시)프로판-2-일)카르바모일)피리딘 1-옥시드의 제조.
메틸렌 클로라이드(1.0 mL)에 용해된 (2S,3S)-3-페닐부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트(54 mg, 0.15 mmol)를 함유하는 용액에 m-CPBA(50 mg, 0.29 mmol)를 첨가하였다. 실온에서 30 min 동안 교반한 후에, 반응 혼합물을 진공에서 농축하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 50% 아세톤/헥산 구배)를 통해 정제하여, 3-히드록시-4-메톡시-2-(((S)-1-옥소-1-(((2S,3S)-3-페닐부탄-2-일)옥시)프로판-2-일)카르바모일)피리딘 1-옥시드(51 mg, 0.13 mmol, 86% 수율)를 점성 담황색 오일로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 14.39 (s, 1H), 12.82 (d, J = 6.9 Hz, 1H), 7.89 (d, J = 7.2 Hz, 1H), 7.32 - 7.25 (m, 2H), 7.25 - 7.15 (m, 3H), 6.78 (d, J = 7.2 Hz, 1H), 5.10 (dq, J = 8.1, 6.3 Hz, 1H), 4.75 - 4.64 (m, 1H), 3.97 (s, 3H), 2.96 - 2.86 (m, 1H), 1.56 (d, J = 7.2 Hz, 3H), 1.30 (d, J = 6.9 Hz, 3H), 1.12 (d, J = 6.2 Hz, 3H); IR (박막) 2978, 2937, 1735, 1643, 1569, 1479, 1452, 1211, 1154, 729, 702 cm-1; HRMS-ESI (m/z) [M+H]+ C20H25N2O6에 대한 계산치, 389.1707; 실측치, 389.1703.
실시예 8: (2S,3S)-3-페닐부탄-2-일 (S)-2-(8-메톡시-2,4-디옥소-2H-피리도[2,3-e][1,3]옥사진-3(4H)-일)프로파노에이트의 제조.
메틸렌 클로라이드(1.0 mL)에 용해된 (2S,3S)-3-페닐부탄-2-일 (3-히드록시-4-메톡시피콜리노일)-L-알라니네이트(54 mg, 0.15 mmol) 및 트리포스겐(86 mg, 0.29 mmol)을 함유하는 용액에 피리딘(0.1 mL, 1.24 mmol)을 첨가하였다. 45 min 동안 교반한 후에, 반응 혼합물을 포화 중탄산나트륨 용액(5 mL)으로 켄칭하고 메틸렌 클로라이드(3 × 5 mL)로 추출하였다. 유기물을 상 분리기에 통과시키고 진공에서 농축하였다. 조 잔류물을, 자동화된 플래시 컬럼 크로마토그래피(SiO2, 0 내지 40% 아세톤/헥산 구배)를 통해 정제하여, (2S,3S)-3-페닐부탄-2-일 (S)-2-(8-메톡시-2,4-디옥소-2H-피리도[2,3-e][1,3]옥사진-3(4H)-일)프로파노에이트(41 mg, 0.10 mmol, 67% 수율)를 황백색 폼(off-white foam)으로서 제공하였다: 1H NMR (500 MHz, CDCl3) δ 8.61 (d, J = 5.3 Hz, 1H), 7.24 - 7.17 (m, 2H), 7.17 - 7.06 (m, 4H), 5.61 (q, J = 7.1 Hz, 1H), 5.16 - 5.06 (m, 1H), 4.06 (s, 3H), 2.93 - 2.83 (m, 1H), 1.70 (d, J = 7.1 Hz, 3H), 1.27 (d, J = 7.1 Hz, 3H), 1.04 (d, J = 6.3 Hz, 3H); IR (박막) 2978, 2942, 1769, 1712, 1602, 1501, 1371, 1242, 1081, 702 cm-1; HRMS-ESI (m/z) [M+H]+ C21H23N2O6에 대한 계산치, 399.1551; 실측치, 399.1549.
실시예 A: 살진균 활성의 평가: 밀 잎마름병(지모세프토리아 트리티시; Bayer 코드 SEPTTR):
공업용 등급의 물질을 아세톤에 용해시키고, 이어서 110 ppm Triton X-100을 함유하는 물 9 부피와 혼합하였다. 자동화 부스 분무기를 사용하여 살진균제 용액을 밀 묘목에 흘러넘치도록 적용하였다. 모든 분무된 식물을 추가의 취급 전에 공기 건조되도록 하였다. 달리 언급되지 않는 한, 상기 언급된 방법을 사용하여 모든 살진균제를 모든 표적 병해에 대한 그의 활성에 대하여 평가하였다. 트랙 분무 적용을 사용하여 밀 잎마름병 및 갈색녹병 활성을 평가하였으며, 이 경우에 분무 용액 중에 0.1% Trycol 5941을 함유하는 EC 제형으로서 살진균제를 제형화하였다.
밀 식물(품종 유마(Yuma))을 온실에서 50% 무기질 토양/50% 무-토양 Metro 믹스에서 종자로부터 제1엽이 완전히 나올 때까지 포트당 7 내지 10개의 묘목으로 성장시켰다. 살진균제 처리 전에 또는 그 후에, 지모세프토리아 트리티시의 수성 포자 현탁액을 이들 식물에 접종하였다. 접종 후, 식물을 100% 상대 습도에서 유지하여 (20℃에서 어두운 듀 챔버(dew chamber)에서 1일에 이어서 밝은 듀 챔버에서 2 내지 3일), 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 식물을 20℃로 설정된 온실로 옮겨서 병해가 발생하도록 하였다. 비처리된 식물의 제1엽에서 병해의 증상이 완전히 발현된 때에, 0 내지 100 퍼센트 병해 중증도의 척도로 감염 수준을 평가하였다. 비처리된 식물에 대한 처리된 식물의 병해 중증도의 비를 사용하여 병해 방제 퍼센트를 계산하였다.
실시예 B: 살진균 활성의 평가: 밀 갈색녹병(푹시니아 트리티시나; 동의어: 푹시니아 레콘디타 분화형 트리티시; Bayer 코드 PUCCRT):
밀 식물(품종 유마)을 온실에서 50% 무기질 토양/50% 무-토양 Metro 믹스에서 종자로부터 제1엽이 완전히 나올 때까지 포트당 7 내지 10개의 묘목으로 성장시켰다. 살진균제 처리 전에 또는 그 후에, 푹시니아 트리티시나의 수성 포자 현탁액을 이들 식물에 접종하였다. 접종 후에, 식물을 22℃에서 100% 상대 습도로 하룻밤 어두운 듀 룸에서 유지하여, 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 식물을 24℃로 설정된 온실로 옮겨서 병해가 발생하도록 하였다. 살진균제 제형화, 적용 및 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 C: 살진균 활성의 평가: 아시아 대두 녹병(Asian Soybean Rust)(파코프소라 파키리지; Bayer 코드 PHAKPA):
공업용 등급의 물질을 아세톤에 용해시키고, 이어서 0.011% Tween 20을 함유하는 물 9 부피와 혼합하였다. 자동화 부스 분무기를 사용하여 살진균제 용액을 대두 묘목에 흘러넘치도록 적용하였다. 모든 분무된 식물을 추가의 취급 전에 공기 건조되도록 하였다.
대두 식물(품종 윌리엄스(Williams) 82)을 무-토양 Metro 믹스에서, 포트당 1개의 식물로 성장시켰다. 2주령 묘목을 시험에 사용하였다. 살진균제 처리 3일 전에 또는 살진균제 처리 1일 후에 식물에 접종하였다. 식물을 22℃ 및 100% 상대 습도로 어두운 듀 룸에서 24 h 동안 인큐베이션하고, 이어서 23℃의 성장실로 옮겨서 병해가 발생하도록 하였다. 분무된 잎에 대해 병해 중증도를 평가하였다.
실시예 D: 살진균 활성의 평가: 토마토 겹무늬병(알테르나리아 솔라니; Bayer 코드 ALTESO):
토마토 식물(품종 아웃도어 걸(Outdoor Girl))을 무-토양 Metro 믹스에서 각 포트가 하나의 식물을 갖도록 번식시키고, 12 내지 14일령이 되었을 때 사용하였다. 살진균제 처리 24 hr 후에 알테르나리아 솔라니의 수성 포자 현탁액을 시험 식물에 접종하였다. 접종 후, 식물을 100% 상대 습도에서 유지하여 (20℃에서 어두운 듀 챔버에서 1일에 이어서 밝은 듀 챔버에서 2 내지 3일), 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 식물을 22℃의 성장실로 옮겨서 병해가 발생하도록 하였다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 E: 살진균 활성의 평가: 사탕무 잎반점병(세르코스포라 베티콜라; Bayer 코드 CERCBE):
사탕무 식물(품종 HH88)을 무-토양 Metro 믹스에서 성장시키고, 시험 전에 주기적으로 잘라내어 균일한 식물 크기를 유지하였다. 살진균제 처리 24 hr 후에 포자 현탁액을 식물에 접종하였다. 접종된 식물을 48 hr 동안 22℃에서 듀 챔버에서 유지하고, 이어서 병해의 증상이 완전히 발현될 때까지 24℃로 설정된 온실에서 바닥 환기를 사용하는 투명 플라스틱 후드 하에서 인큐베이션하였다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 F: 살진균 활성의 평가: 오이 탄저병(글로메렐라 라게나리움; 불완전세대: 콜레토트리쿰 라게나리움; Bayer 코드 COLLLA):
오이 묘목(품종 부쉬 피클(Bush Pickle))을 무-토양 Metro 믹스에서 각 포트가 1개의 식물을 갖도록 번식시키고, 12 내지 14일령이 되었을 때 시험에 사용하였다. 살진균제 처리 24 hr 후에 콜레토트리쿰 라게나리움의 수성 포자 현탁액을 시험 식물에 접종하였다. 접종 후에, 식물을 22℃에서 100% 상대 습도로 48 hr 동안 듀 룸에서 유지하여, 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 식물을 22℃로 설정된 온실로 옮겨서 병해가 발생하도록 하였다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 G: 살진균 활성의 평가: 밀 껍질마름병(파라스타고노스포라 노도룸; Bayer 코드 LEPTNO):
밀 식물(품종 유마)을 온실에서 50% 무기질 토양/50% 무-토양 Metro 믹스에서 종자로부터 제1엽이 완전히 나올 때까지 포트당 7 내지 10개의 묘목으로 성장시켰다. 살진균제 처리 24 hr 후에 파라스타고노스포라 노도룸의 수성 포자 현탁액을 이러한 식물에 접종하였다. 접종 후, 식물을 100% 상대 습도에서 유지하여 (20℃에서 어두운 듀 챔버에서 1일에 이어서 밝은 듀 챔버에서 2일), 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 식물을 20℃로 설정된 온실로 옮겨서 병해가 발생하도록 하였다. 살진균제 제형화, 적용 및 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 H: 살진균 활성의 평가: 오이 노균병(Cucumber Downy Mildew)(슈도페로노스포라 쿠벤시스; Bayer 코드 PSPECU):
오이 묘목(품종 부쉬 피클)을 무-토양 Metro 믹스에서, 포트당 1개의 식물로 성장시키고, 12 내지 14일령이 되었을 때 시험에 사용하였다. 살진균제 처리 24 hr 후에 포자 현탁액을 식물에 접종하였다. 살진균제 처리 24 hr 후에 슈도페로노스포라 쿠벤시스의 수성 포자 현탁액을 시험 식물에 접종하였다. 접종 후에, 식물을 22℃에서 100% 상대 습도로 24 hr 동안 듀 룸에서 유지하여, 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 병해가 완전히 발현될 때까지 식물을 20℃로 설정된 온실로 옮겼다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 I: 살진균 활성의 평가: 도열병(Rice Blast)(마그나포르테 그리세아; 불완전세대: 피리쿨라리아 오리자에; Bayer 코드 PYRIOR):
벼 묘목(품종 자포니카(Japonica))을 무-토양 Metro 믹스에서 각 포트가 8 내지 14개의 식물을 갖도록 번식시키고, 12 내지 14일령이 되었을 때 시험에 사용하였다. 살진균제 처리 24 hr 후에 피리쿨라리아 오리자에의 수성 포자 현탁액을 시험 식물에 접종하였다. 접종 후에, 식물을 22℃에서 100% 상대 습도로 48 hr 동안 듀 룸에서 유지하여, 포자가 발아하여 잎을 감염시키도록 하였다. 이어서 식물을 24℃로 설정된 온실로 옮겨서 병해가 발생하도록 하였다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 J: 살진균 활성의 평가: 보리 구름무늬병(린코스포리움 세칼리스; Bayer 코드 RHYNSE):
보리 묘목(품종 해링턴(Harrington))을 무-토양 Metro 믹스에서 각 포트가 8 내지 12개의 식물을 갖도록 번식시키고, 제1엽이 완전히 나왔을 때 시험에 사용하였다. 살진균제 처리 24 hr 후에 린코스포리움 세칼리스의 수성 포자 현탁액을 시험 식물에 접종하였다. 접종 후, 식물을 48 hr 동안 100% 상대 습도로 20℃에서 듀 룸에서 유지하였다. 이어서 식물을 20℃로 설정된 온실로 옮겨서 병해가 발생하도록 하였다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
실시예 K: 살진균 활성의 평가: 포도 흰가루병(운시눌라 네카토르; Bayer 코드 UNCINE):
포도 묘목(품종 캐리낸(Carignane))을 무-토양 Metro 믹스에서, 포트당 1개의 식물로 성장시키고, 대략 1개월령이 되었을 때 시험에 사용하였다. 살진균제 처리 24 hr 후에, 감염된 잎으로부터의 포자를 시험 식물 위에서 흔들어서 식물에 접종하였다. 병해가 완전히 발현될 때까지 식물을 20℃로 설정된 온실에서 유지하였다. 살진균제 제형화, 적용 및 분무된 잎에 대한 병해 평가는 실시예 A에 기재된 바와 같은 절차에 따랐다.
[표 1] 화합물 구조, 외관, 및 제조 방법
[표 2] 분석 데이터
[표 3] 생물학적 시험 등급 척도
[표 4] 생물학적 활성 - 다량 적용에서의 PUCCRT 및 SEPTTR 병해 방제
[표 5] 생물학적 활성 - 소량 적용에서의 PUCCRT 및 SEPTTR 병해 방제
[표 6] 생물학적 활성 - 25 ppm에서의 다량 병해 방제
[표 7] 생물학적 활성 - 100 ppm에서 1DP* 시험에서의 병해 방제
[표 8] 생물학적 활성 - 100 ppm에서 1DP* 시험에서의 병해 방제
Claims (28)
- 하기 화학식 I의 화합물:
[화학식 I]
(여기서,
Q는 이고;
X는 수소 또는 C(O)R4이고;
Y는 수소 또는 C(O)R4이고;
Z는 N 또는 N+→O-이고 W는 O 또는 S이고;
R1은 수소 또는 알킬이며, 이는 0개, 1개 또는 다수개의 R7로 치환되고;
R2는 메틸이고;
R3은 알킬, 아릴 또는 헤테로아릴이며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R4는 알콕시 또는 벤질옥시이며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R5는 수소, 알콕시, 또는 할로이며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R6은 수소, -C(O)R8, 또는 -CH2OC(O)R8이고;
R7은 수소, 알킬, 아릴, 아실, 할로, 알케닐, 알키닐, 알콕시, 시아노, 또는 헤테로시클릴이며, 각각은 선택적으로 0개, 1개 또는 다수개의 R9로 치환되고;
R8은 알킬, 알콕시, 또는 아릴이며, 각각은 선택적으로 0개, 1개 또는 다수개의 R7로 치환되고;
R9는 수소, 알킬, 아릴, 아실, 할로, 알케닐, 알콕시, 또는 헤테로시클릴이고;
R10은 수소 또는 알킬이며, 각각은 0개, 1개 또는 다수개의 R7로 치환됨). - 제2항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되는, 화합물.
- 제2항에 있어서, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제2항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되고, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제6항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되는, 화합물.
- 제6항에 있어서, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제6항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되고, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제10항에 있어서, Z는 N인, 화합물.
- 제11항에 있어서, W는 O인, 화합물.
- 제12항에 있어서, R5는 알콕시인, 화합물.
- 제13항에 있어서, R6은 수소인, 화합물.
- 제14항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되는, 화합물.
- 제14항에 있어서, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제14항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되고, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제13항에 있어서, R6은 -C(O)R8 또는 -CH2OC(O)R8로부터 선택되는, 화합물.
- 제18항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되는, 화합물.
- 제18항에 있어서, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제18항에 있어서, R1 및 R10은 독립적으로 수소 또는 알킬로부터 선택되고, R3은 0개, 1개 또는 다수개의 R7로 선택적으로 치환된 아릴인, 화합물.
- 제1항 내지 제21항의 화합물 중 어느 하나를 포함하는 항진균 조성물.
- 제22항에 있어서, 하나 이상의 살진균제, 살충제, 살선충제, 살진드기제, 살절지동물제(arthropodicide), 살균제 및 이들의 조합을 추가로 포함하는, 조성물.
- 제1항 내지 제21항의 화합물 중 적어도 하나와 살진균제, 살충제, 살선충제, 살진드기제, 살절지동물제, 살균제 및 이들의 조합을 포함하는 또 다른 농약을 포함하는, 진균 병원체의 방제를 위한 조성물.
- 제24항에 있어서, 상기 진균 병원체는 밀 잎마름병(Leaf Blotch of Wheat)(지모세프토리아 트리티시(Zymoseptoria tritici)), 밀 갈색녹병(Wheat Brown Rust)(푹시니아 트리티시나(Puccinia triticina)), 줄녹병(Stripe Rust)(푹시니아 스트리이포르미스(Puccinia striiformis)), 사과 검은별무늬병(Scab of Apple)(벤투리아 이나에쿠알리스(Venturia inaequalis)), 옥수수 수포 깜부기병(Blister Smut of Maize)(우스틸라고 마이디스(Ustilago maydis)), 포도덩굴 흰가루병(Powdery Mildew of Grapevine)(운시눌라 네카토르(Uncinula necator)), 보리 구름무늬병(Barley Scald)(린코스포리움 세칼리스(Rhynchosporium secalis)), 도열병(Blast of Rice)(피리쿨라리아 오리자에(Pyricularia oryzae)), 대두 녹병(Rust of Soybean)(파코프소라 파키리지(Phakopsora pachyrhizi)), 밀 껍질마름병(Glume Blotch of Wheat)(파라스타고노스포라 노도룸(Parastagonospora nodorum)), 밀 흰가루병(Powdery Mildew of Wheat)(블루메리아 그라미니스 분화형 트리티시(Blumeria graminis f. sp.tritici)), 보리 흰가루병(Powdery Mildew of Barley)(블루메리아 그라미니스 분화형 호르데이(Blumeria graminis f. sp. hordei)), 박과 흰가루병(Powdery Mildew of Cucurbits)(에리시페 시코라세아룸(Erysiphe cichoracearum)), 박과 탄저병(Anthracnose of Cucurbits)(콜레토트리쿰 라게나리움(Colletotrichum lagenarium)), 비트 입반점병(Leaf Spot of Beet)(세르코스포라 베티콜라(Cercospora beticola)), 토마토 겹무늬병(Early Blight of Tomato)(알테르나리아 솔라니(Alternaria solani)), 오이 노균병(Cucumber Downy Mildew)(슈도페로노스포라 쿠벤시스(Pseudoperonospora cubensis)), 및 보리 망반병(Net Blotch of Barley)(피레노포라 테레스(Pyrenophora teres)) 중 하나인, 조성물.
- 제24항에 있어서, 상기 진균 병원체는 밀 잎마름병(지모세프토리아 트리티시), 밀 갈색녹병(푹시니아 트리티시나), 보리 구름무늬병(린코스포리움 세칼리스), 도열병(피리쿨라리아 오리자에), 대두 녹병(파코프소라 파키리지), 밀 껍질마름병(파라스타고노스포라 노도룸), 박과 탄저병(콜레토트리쿰 라게나리움), 비트 입반점병(세르코스포라 베티콜라), 포도덩굴 흰가루병(운시눌라 네카토르), 오이 노균병(슈도페로노스포라 쿠벤시스), 및 토마토 겹무늬병(알테르나리아 솔라니) 중 하나인, 조성물.
- 식물에 대한 진균 공격을 방제 및 예방하는 방법으로서,
살진균 유효량의 제1항 내지 제21항 중 임의의 항의 화합물 중 적어도 하나를 상기 식물, 상기 식물에 인접한 영역, 상기 식물의 성장을 지원하기에 적합한 토양, 상기 식물의 뿌리, 및 상기 식물의 잎(foliage) 중 적어도 하나에 적용하는 단계를 포함하는, 방법. - 식물에 대한 진균 공격을 방제 및 예방하는 방법으로서,
살진균 유효량의 제22항 및 제23항 중 임의의 항의 조성물 중 적어도 하나를 상기 식물, 상기 식물에 인접한 영역, 상기 식물의 성장을 지원하기에 적합한 토양, 상기 식물의 뿌리, 및 상기 식물의 잎 중 적어도 하나에 적용하는 단계를 포함하는, 방법.
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BR112017000169A2 (pt) | 2014-07-08 | 2017-10-31 | Dow Agrosciences Llc | picolinamidas macrocíclicas como fungicidas |
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2019
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- 2019-03-08 KR KR1020207028745A patent/KR20200129141A/ko not_active Application Discontinuation
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AU2019231764A1 (en) | 2020-10-01 |
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CN115745877A (zh) | 2023-03-07 |
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UY38140A (es) | 2019-10-31 |
JP2021515020A (ja) | 2021-06-17 |
BR102019004480B1 (pt) | 2023-03-28 |
US11155520B2 (en) | 2021-10-26 |
US20230049481A1 (en) | 2023-02-16 |
EP3761790A4 (en) | 2021-11-10 |
US20190276404A1 (en) | 2019-09-12 |
BR102019004480A2 (pt) | 2019-10-01 |
CR20200393A (es) | 2020-11-23 |
ZA202005639B (en) | 2023-02-22 |
CO2020012505A2 (es) | 2020-10-30 |
CN112040773A (zh) | 2020-12-04 |
CL2020002311A1 (es) | 2021-01-15 |
JP7336452B2 (ja) | 2023-08-31 |
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