KR20210031475A - 항박테리아제로서의 치환된 티오펜카르복스아미드 및 유사체 - Google Patents
항박테리아제로서의 치환된 티오펜카르복스아미드 및 유사체 Download PDFInfo
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- KR20210031475A KR20210031475A KR1020217003297A KR20217003297A KR20210031475A KR 20210031475 A KR20210031475 A KR 20210031475A KR 1020217003297 A KR1020217003297 A KR 1020217003297A KR 20217003297 A KR20217003297 A KR 20217003297A KR 20210031475 A KR20210031475 A KR 20210031475A
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- 239000003242 anti bacterial agent Substances 0.000 title description 4
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 title 1
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 237
- 238000000034 method Methods 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 53
- 229910052801 chlorine Inorganic materials 0.000 claims description 49
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 49
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- 235000013399 edible fruits Nutrition 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- JAARIXSMRWKNFX-UHFFFAOYSA-N 4,5-dibromo-3-fluorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Br)=C(Br)C=1F JAARIXSMRWKNFX-UHFFFAOYSA-N 0.000 claims description 3
- QEZRPOCNDKTQJO-UHFFFAOYSA-N 3,4,5-tribromothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Br)=C(Br)C=1Br QEZRPOCNDKTQJO-UHFFFAOYSA-N 0.000 claims description 2
- XOUIIPXNMPQGGQ-UHFFFAOYSA-N 4,5-dibromo-3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Br)=C(Br)C=1Cl XOUIIPXNMPQGGQ-UHFFFAOYSA-N 0.000 claims description 2
- KUXNSSLEHIUORH-UHFFFAOYSA-N 4,5-dibromo-3-methylthiophene-2-carboxylic acid Chemical compound CC=1C(Br)=C(Br)SC=1C(O)=O KUXNSSLEHIUORH-UHFFFAOYSA-N 0.000 claims description 2
- XZOTWSGVXFPSJX-UHFFFAOYSA-N 4,5-dichloro-3-methylthiophene-2-carboxylic acid Chemical compound CC=1C(Cl)=C(Cl)SC=1C(O)=O XZOTWSGVXFPSJX-UHFFFAOYSA-N 0.000 claims description 2
- PJVUDYYMBPNSCN-UHFFFAOYSA-N FC1=C(SC(=C1Cl)Cl)C(=O)O Chemical compound FC1=C(SC(=C1Cl)Cl)C(=O)O PJVUDYYMBPNSCN-UHFFFAOYSA-N 0.000 claims description 2
- 238000007080 aromatic substitution reaction Methods 0.000 claims description 2
- GKKNVRTWKLFMGM-UHFFFAOYSA-N ethyl 3,4,5-tribromothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=C(Br)C=1Br GKKNVRTWKLFMGM-UHFFFAOYSA-N 0.000 claims description 2
- LSBUOEYCPAQAHW-UHFFFAOYSA-N ethyl 4,5-dibromo-3-chlorothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=C(Br)C=1Cl LSBUOEYCPAQAHW-UHFFFAOYSA-N 0.000 claims description 2
- PMPBGORMHXRHRT-UHFFFAOYSA-N ethyl 5-amino-4-bromo-3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(N)=C(Br)C=1C PMPBGORMHXRHRT-UHFFFAOYSA-N 0.000 claims description 2
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- DKJRFAFPCROFRG-UHFFFAOYSA-N methyl 3,4,5-tribromothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1Br DKJRFAFPCROFRG-UHFFFAOYSA-N 0.000 claims description 2
- RJQBWMPIDVDQQA-UHFFFAOYSA-N methyl 4,5-dibromo-3-chlorothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1Cl RJQBWMPIDVDQQA-UHFFFAOYSA-N 0.000 claims description 2
- CUZHIRPKCADYDJ-UHFFFAOYSA-N methyl 4,5-dibromo-3-fluorothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1F CUZHIRPKCADYDJ-UHFFFAOYSA-N 0.000 claims description 2
- WQCQDITXZPVXGB-UHFFFAOYSA-N methyl 4,5-dibromo-3-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1C WQCQDITXZPVXGB-UHFFFAOYSA-N 0.000 claims description 2
- ONBHJNHOAHJNOU-UHFFFAOYSA-N methyl 4,5-dichloro-3-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Cl)=C(Cl)C=1C ONBHJNHOAHJNOU-UHFFFAOYSA-N 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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- 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
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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- A01P13/00—Herbicides; Algicides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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Abstract
본 개시내용은 박테리아성 질병으로부터, 특히 크산토모나스 속에 속하는 박테리아에 의해 유발된 박테리아성 질병으로부터 식물을 보호하는 데 사용될 수 있는 하기 화학식 (III)의 티에닐옥사졸론 및 그의 유사체에 관한 것이다.
Description
본 발명은 특히 크산토모나스(Xanthomonas) 속에 속하는 박테리아에 의해 유발되는 박테리아성 질병으로부터 식물을 보호하는 데 사용될 수 있는 티에닐옥사졸론 및 그의 유사체에 관한 것이다.
식물 병원성 박테리아는 전세계적으로 심각한 경제적 손해를 입히는 질병을 야기할 수 있다. 크산토모나스 속에 속하는 박테리아는 가장 파괴적인 것으로 간주되는 식물 병원성 박테리아 중 하나이다. 이들은 농경학상 중요성을 갖는 여러 숙주 식물에 대한 다양한 질병의 병원체이다. 이러한 질병의 예는 페퍼 및 토마토에 영향을 미치는 박테리아성 점무늬병 (크산토모나스 캄페스트리스 병원체변종 베시카토리아(Xanthomonas campestris pv. vesicatoria)에 의해 유발됨), 모든 재배품종 브라시카 (예를 들어 브뤼셀 스프라우트, 양배추, 콜리플라워 및 브로콜리)에 영향을 미치는 십자화과의 검은 썩음병 (크산토모나스 캄페스트리스 병원체변종 캄페스트리스(Xanthomonas campestris pv. campestris)에 의해 유발됨), 시트러스 종 (라임, 오렌지, 자몽, 유자)에 영향을 미치는 시트러스 동고병 (크산토모나스 악소노포디스 병원체변종 시트리(Xanthomonas axonopodis pv. citri)에 의해 유발됨), 벼에 영향을 미치는 박테리아성 잎마름병 (크산토모나스 오리자에 병원체변종 오리자에(Xanthomonas oryzae pv. oryzae)에 의해 유발됨), 프루누스(Prunus) 종 (예를 들어 살구, 자두, 복숭아)에 영향을 미치는 잎점무늬병 (크산토모나스 아르보리콜라 병원체변종 프루니(Xanthomonas arboricola pv. pruni)에 의해 유발됨), 콩에 영향을 미치는 박테리아성 마름병 (크산토모나스 파세올리(Xanthomonas phaseoli)에 의해 유발됨), 카사바에 영향을 미치는 카사바 박테리아성 마름병 (크산토모나스 악소노포디스 병원체변종 마니호티스(Xanthomonas axonopodis pv. manihotis)에 의해 유발됨) 및 목화에 영향을 미치는 모무늬병/박테리아성 마름병 (크산토모나스 캄페스트리스 병원체변종 말라바세아룸(Xanthomonas campestris pv. malvacearum)에 의해 유발됨)을 포함한다.
박테리아성 식물 질병은 주로 질병-저항성 식물 품종의 사용 및 살박테리아제 (천연 또는 합성)의 사용을 비롯한 다양한 방식으로 방제될 수 있다. 의약에서의 항생제 내성 위기 및 일부 항생제 내성 식물 병원체의 출현은 항생제의 효능을 보존하고 질병 관리 해결책의 범주를 확장시키기 위한 항생제에 대한 대체제의 개발을 촉발하였다. 이에 따라, 병원성 박테리아에 직접적으로 작용하지 않는, 즉 직접적인 항생제 효과는 없지만 식물 자신의 방어 시스템을 자극하는 제품이 개발되었다. 이들 제품은 식물 방어 활성화제로서 공지되어 있다. 식물 방어 활성화제의 예는 아시벤졸라르-S-메틸 (비온(Bion)® 및 액티가드(Actigard)®로서 시판됨), 2,6-디클로로이소니코틴산, β-아미노부티르산, 프로베나졸 (오리제메이트(Oryzemate)®), 살리실산, 리보플라빈, 프로헥사디온-칼슘, 포타슘 포스포네이트, 하르핀(harpin) 단백질 (메신저(Messenger)®) 및 메틸 자스모네이트를 포함한다.
많은 상이한 유기 및 무기 화합물들이 식물에서 유도된 내성을 활성화시키는 것으로 제시되었지만, 현재 몇 가지 제품만이 상업적으로 시판되고 있다.
따라서, 내성 발생을 방지하기 위해 박테리아와 직접적으로 상호작용하지 않으면서, 박테리아성 질병, 특히 크산토모나스 속에 속하는 박테리아에 의해 야기되는 질병을 저용량으로 효율적으로 방제하는 것을 가능하게 하는 새로운 화학물질 및 방법을 제공할 필요가 남아있다. 화학물질이 박테리아와 직접적으로 상호작용하지 않기 때문에, 이들 화학물질에 대한 내성이 발생할 가능성은 없다.
본 발명자들은 티에닐옥사졸론의 부류에 속하는 신규 화학물질이 상기 문제에 대한 해결책을 제공한다는 것을 입증하였다.
일부 티에닐옥사졸론은 식물 질병을 퇴치하는 데 유용한 것으로 공지되어 있다. 예를 들어, WO2004/062361은 진균성 질병을 방제하는 데 효과적인 것으로 언급되는 화합물을 개시한다. 이들은 바람직하지 않은 미생물에 대한 직접적인 효과를 통해서 뿐만 아니라 식물에 대한 저항성 유도 효과로 인해 그의 작용을 발휘할 것이다. WO2004/062361은 또한 이들 화합물이 박테리아성 질병을 방제하는 데 유용할 수 있음을 시사하지만, 이러한 활성의 어떠한 증거도 제공하지 않는다. 이들 화합물은 크산토모나스 캄페스트리스 병원체변종 캄페스트리스에 대해 저용량에서는 효율성이 좋지 않은 것으로 본 발명자들에 의해 밝혀졌다.
요약
본 발명은 청구범위에 언급된 바와 같은 화학식 (III)의 화합물, 뿐만 아니라 그의 제조를 위한 방법 및 중간체에 관한 것이다.
본 발명은 또한 본원에 기재된 바와 같은 박테리아성 질병을 방제하는 방법에 관한 것이다.
상세한 설명
하기 제시된 바와 같은 화학식 (III)의 화합물은 저용량 (즉, 31 ppm만큼 낮은 용량)에서 크산토모나스 속의 박테리아에 의해 유발된 질병을, 직접적인 살박테리아제 작용을 나타내지 않으면서 효율적으로 방제하는 것으로 밝혀졌다.
따라서, 본 발명은 하기 화학식 (III)의 화합물에 관한 것이다.
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이다.
자연 법칙에 위배되고 따라서 통상의 기술자가 그의 전문 지식에 기초하여 제외할 조합으로부터 생성되는 화합물은 본원에 포괄되지 않는다. 예를 들어, 3개 이상의 인접한 산소 원자를 갖는 고리 구조는 제외된다.
치환기의 성질에 따라, 화학식 (III)의 화합물은 상이한 입체이성질체 형태로 존재할 수 있다. 이들 입체이성질체는, 예를 들어 거울상이성질체, 부분입체이성질체, 회전장애이성질체 또는 기하 이성질체이다. 따라서, 본 발명은 순수한 입체이성질체 및 이들 이성질체의 임의의 혼합물 둘 다를 포괄한다. 화합물이 2종 이상의 호변이성질체 형태로 평형 상태로 존재할 수 있는 경우에, 한 호변이성질체 설명에 의한 화합물에 대한 언급은 모든 호변이성질체 형태를 포함하는 것으로 간주될 것이다.
본 발명의 임의의 화합물은 또한 화합물 내 이중 결합의 수에 따라 하나 이상의 기하 이성질체 형태로 존재할 수 있다. 이중 결합 또는 고리 주위의 치환기의 성질에 의한 기하 이성질체는 시스 (= Z-) 또는 트랜스 (= E-) 형태로 존재할 수 있다. 따라서, 본 발명은 한편으로는, 모든 기하 이성질체 및 모든 비율의 모든 가능한 혼합물에 관한 것이다.
화학식 (III)의 화합물은 적합하게는 그의 유리 형태, 염 형태, N-옥시드 형태 또는 용매화물 형태 (예를 들어, 수화물)일 수 있다.
치환기의 성질에 따라, 화학식 (III)의 화합물은 유리 화합물 및/또는 그의 염, 예컨대 농약 활성 염의 형태로 존재할 수 있다.
농약 활성 염은 무기 및 유기 산의 산 부가염뿐만 아니라 통상의 염기의 염을 포함한다. 무기 산의 예는 할로겐화수소산, 예컨대 플루오린화수소, 염화수소, 브로민화수소 및 아이오딘화수소, 황산, 인산, 및 질산 및 산성 염, 예컨대 중황산나트륨 및 중황산칼륨이다. 유용한 유기 산은 예를 들어 포름산, 탄산 및 알칸산, 예컨대 아세트산, 트리플루오로아세트산, 트리클로로아세트산 및 프로피온산, 및 또한 글리콜산, 티오시안산, 락트산, 숙신산, 시트르산, 벤조산, 신남산, 옥살산, 6 내지 20개의 탄소 원자를 갖는 포화 또는 단일- 또는 이중불포화 지방산, 알킬황산 모노에스테르, 알킬술폰산 (1 내지 20개의 탄소 원자를 갖는 직쇄 또는 분지형 알킬 라디칼을 갖는 술폰산), 아릴술폰산 또는 아릴디술폰산 (1 또는 2개의 술폰산 기를 보유하는 방향족 라디칼, 예컨대 페닐 및 나프틸), 알킬포스폰산 (1 내지 20개의 탄소 원자를 갖는 직쇄 또는 분지형 알킬 라디칼을 갖는 포스폰산), 아릴포스폰산 또는 아릴디포스폰산 (1 또는 2개의 포스폰산 라디칼을 보유하는 방향족 라디칼, 예컨대 페닐 및 나프틸)을 포함하며, 여기서 알킬 및 아릴 라디칼은 추가의 치환기, 예를 들어 p-톨루엔술폰산, 살리실산, p-아미노살리실산, 2-페녹시벤조산, 2-아세톡시벤조산 등을 보유할 수 있다.
화학식 (III)의 화합물 또는 그의 염의 용매화물은 상기 화합물과 용매의 화학량론적 조성물이다.
화학식 (III)의 화합물은 다수의 결정질 및/또는 무정형 형태로 존재할 수 있다. 결정질 형태는 비용매화 결정질 형태, 용매화물 및 수화물을 포함한다.
일부 실시양태에서, 본 발명은 하기 화학식 (III)의 화합물에 관한 것이다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자 또는 메틸이다.
일부 실시양태에서, 본 발명에 따른 화합물은 R3이 R1 및 R2와 상이한, 상기 개시된 바와 같은 화학식 (III)의 화합물이다.
본 발명은 표 III.1에 개시된 임의의 화합물에 관한 것이다.
화학식 (III)의 화합물은 박테리아성 질병의 방제, 특히 크산토모나스 속에 속하는 박테리아에 의해 유발된 질병의 방제에 사용될 수 있다.
화학식 (III)의 화합물의 제조 방법
본 발명은 화학식 (III)의 화합물의 제조 방법에 관한 것이다. 화학식 (III)의 화합물은 공지된 방법 (본원의 참고문헌 참조)과 유사한 다양한 경로에 의해, 그리고 하기 본원 및 실험 파트에 기재된 하기 합성 경로 중 하나 이상에 의해 제조될 수 있다.
달리 나타내지 않는 한, 하기에서, R1, R2 및 R3은 화학식 (III)의 화합물에 대해 상기 제공된 것과 동일한 의미를 갖는다.
방법 A3
본원에 정의된 바와 같은 화학식 (III)의 화합물은 하기 반응식에 예시된 바와 같이 고리화 반응에 의해 R4가 수소 원자인 화학식 (XXI)의 화합물 또는 그의 염 중 1종으로부터 방법 A3에 의해 제조될 수 있다.
방법 A3은 문헌 [Journal of Heterocyclic Chemistry, 25(1), 209-215; 1988]; WO 2007003536에 기재된 바와 같이 수행될 수 있다.
방법 A3은, 적절한 경우에, 적합한 브뢴스테드 산, 루이스 산 또는 다른 축합제의 존재 하에, 적절한 경우에, 적합한 산 결합제의 존재 하에 및 적절한 경우에 용매의 존재 하에 수행될 수 있다.
방법 A3을 수행하는 데 적합한 루이스 산은 이러한 반응에 통상적인 무기 및 유기 루이스 산일 수 있다. 금속 할라이드, 예컨대 염화알루미늄(III), 염화철(III), 염화아연(II), 사염화티타늄, 삼플루오린화붕소; 트리플레이트, 예컨대 트리플산스칸듐(III), 트리플산비스무트(III) 또는 트리플산이테르븀(III) 및 또한 아이오딘을 사용하는 것이 바람직하다.
방법 A3을 수행하는 데 적합한 브뢴스테드산은 이러한 반응에 통상적인 무기 및 유기 브뢴스테드산일 수 있다. 할로겐화수소, 예컨대 염화수소 또는 브로민화수소; 술폰산, 예컨대 p-톨루엔술폰산, 캄포르술폰산, 메탄술폰산 또는 트리플루오로메탄술폰산 및 또한 폴리인산, 인산 황산, 중아황산칼륨, 트리플루오로아세트산 또는 아세트산을 사용하는 것이 바람직하다.
방법 A3을 수행하는 데 적합한 다른 축합제는 산 할라이드 형성제, 예컨대 포스겐, 삼브로민화인, 삼염화인, 오염화인, 삼염화인 옥시드, 옥살릴 클로라이드 또는 티오닐 클로라이드; 무수물 형성제, 예컨대 에틸 클로로포르메이트, 메틸 클로로포르메이트, 이소프로필 클로로포르메이트, 이소부틸 클로로포르메이트 또는 메탄술포닐 클로라이드; 무수물, 예컨대 트리플루오로아세트산 무수물 또는 아세트산 무수물; 카르보디이미드, 예컨대 N,N'-디시클로헥실카르보디이미드 (DCC), N-(3-디메틸아미노프로필)-N'-에틸카르보디이미드 히드로클로라이드 (EDC) 또는 다른 통상의 축합제, 예컨대 오산화인, 폴리인산, 비스(2-옥소-3-옥사졸리디닐)포스핀산 클로라이드, 1-[비스(디메틸아미노)메틸렌]-1H-1,2,3-트리아졸로[4,5-b]피리디늄 3-옥시드 헥사플루오로포스페이트 (HATU), 2-(1H-벤조트리아졸-1-일)-1,1,3,3-테트라메틸아미늄 테트라플루오로보레이트 (TBTU), (1-시아노-2-에톡시-2-옥소에틸리덴아미노옥시)디메틸아미노-모르폴리노-카르베늄 헥사플루오로포스페이트, N,N'-카르보닐-디이미다졸, 2-에톡시-N-에톡시카르보닐-1,2-디히드로퀴놀린 (EEDQ), 트리페닐포스핀/테트라클로로-메탄, 4-(4,6-디메톡시[1.3.5]-트리아진-2-일)-4-메틸모르폴리늄 클로라이드 수화물, 비스(2-옥소-3-옥사졸리디닐)포스핀산 클로라이드 (BOP-Cl), 브로모-트리피롤리디노포스포늄헥사플루오로포스페이트 (PyBroP), 2-클로로-1,3-디메틸이미다졸리늄 클로라이드 (DMC) 또는 프로판포스폰산 무수물 (T3P)로 이루어진 비제한적 목록에서 선택될 수 있다.
본 발명에 따른 방법 A3을 수행하는 데 적합한 산 결합제는 각 경우에 이러한 반응에 통상적인 모든 무기 및 유기 염기이다. 알칼리 금속 탄산염, 예컨대 탄산세슘, 탄산나트륨, 탄산칼륨, 중탄산칼륨, 중탄산나트륨, 알칼리 토금속 아세테이트, 예컨대 아세트산나트륨, 아세트산칼륨, 아세트산칼슘 및 또한 3급 아민, 예컨대 트리메틸아민, 트리에틸아민, 디이소프로필에틸아민, 트리부틸아민, N,N-디메틸아닐린, N-메틸피페리딘, N,N-디메틸피리딘-4-아민, 디아자비시클로옥탄 (DABCO), 디아자비시클로-노넨 (DBN) 또는 디아자비시클로운데센 (DBU), 또는 방향족 염기, 예컨대 피리딘이 바람직하다.
방법 A3을 수행하는 데 적합한 용매는 특별히 제한되지 않는다. 이들은, 화합물과 반응하거나 그와 임의의 특정한 상호작용을 나타내도록 화합물을 용해시키지 않는 한, 통상의 불활성 유기 용매일 수 있다. 임의로 할로겐화, 지방족, 지환족 또는 방향족 탄화수소, 예컨대 석유 에테르, 펜탄, 헥산, 헵탄, 시클로헥산, 메틸시클로헥산, 벤젠, 톨루엔, 크실렌, 데칼린, 이소파르(ISOPAR)™ E 또는 이소파르™ G, 클로로벤젠, 디클로로벤젠, 디클로로메탄, 클로로포름, 사염화탄소, 1,2-디클로로에탄 또는 트리클로로에탄; 에테르, 예컨대 디에틸 에테르, 디이소프로필 에테르, 메틸 tert-부틸 에테르, 메틸 tert-아밀 에테르, 디옥산, 테트라히드로푸란, 2-메틸테트라히드로푸란, 1,2-디메톡시에탄, 1,2-디에톡시에탄 또는 아니솔; 니트릴, 예컨대 아세토니트릴, 프로피오니트릴, n- 또는 이소-부티로니트릴 또는 벤조니트릴; 아미드, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸포름아닐리드, N-메틸피롤리돈 또는 헥사메틸포스포릭 트리아미드; 우레아, 예컨대 1,3-디메틸-3,4,5,6-테트라히드로-2(1H)-피리미디논; 에스테르, 예컨대 메틸 아세테이트 또는 에틸 아세테이트, 술폭시드, 예컨대 디메틸 술폭시드 또는 술폰, 예컨대 술폴란; 및 그의 혼합물을 사용하는 것이 바람직하다.
방법 A3은 불활성 분위기에서 수행될 수 있다. 방법 A3을 수행할 때, 화학식 (XXI)의 화합물 1 몰당 0.01 내지 5 몰 퍼센트의 적합한 산 또는 축합제가 사용될 수 있고 화학식 (XXI)의 화합물 1 몰당 0.01 내지 5 몰의 산 결합제가 사용될 수 있다. 반응 성분을 다른 비로 사용하는 것이 또한 가능하다. 후처리는 공지된 방법에 의해 수행된다.
R4가 수소 원자를 나타내는 화학식 (XXI)의 화합물은 R4가 C1-C6-알킬을 나타내는 화학식 (XXI)의 화합물로부터 널리 공지된 방법, 예컨대 염기성 가수분해에 의해 제조될 수 있다.
화학식 (XXI)의 화합물의 제조 - 방법 PXXI(1)
R4가 수소 원자 또는 C1-C6-알킬인 화학식 (XXI)의 화합물은 하기 반응식에 예시된 바와 같이 화학식 (XXII)의 화합물을 화학식 (XXIII)의 화합물 또는 그의 염 중 1종과 반응시키는 단계를 포함하는 방법 PXXI(1)에 의해 제조될 수 있다:
여기서 R4는 수소 원자 또는 C1-C6-알킬이고, U1은 할로겐 원자, 히드록시 기 또는 C1-C6-알콕시 기이다.
U1이 히드록시 기를 나타내는 경우에, 본 발명에 따른 방법 PXXI(1)은 유리하게는 축합제의 존재 하에 수행된다. 적합한 축합제는 산 할라이드 형성제, 예컨대 포스겐, 삼브로민화인, 삼염화인, 오염화인, 삼염화인 옥시드, 옥살릴 클로라이드 또는 티오닐 클로라이드; 무수물 형성제, 예컨대 에틸 클로로포르메이트, 메틸 클로로포르메이트, 이소프로필 클로로포르메이트, 이소부틸 클로로포르메이트 또는 메탄술포닐 클로라이드; 카르보디이미드, 예컨대 N,N'-디시클로헥실카르보디이미드 (DCC), N-(3-디메틸아미노프로필)-N'-에틸카르보디이미드 히드로클로라이드 (EDC) 또는 다른 통상의 축합제, 예컨대 오산화인, 폴리인산, 비스(2-옥소-3-옥사졸리디닐)포스핀산 클로라이드, 1-[비스(디메틸아미노)메틸렌]-1H-1,2,3-트리아졸로[4,5-b]피리디늄 3-옥시드 헥사플루오로포스페이트 (HATU), 2-(1H-벤조트리아졸-1-일)-1,1,3,3-테트라메틸아미늄 테트라플루오로보레이트 (TBTU), (1-시아노-2-에톡시-2-옥소에틸리덴아미노옥시)디메틸아미노-모르폴리노-카르베늄 헥사플루오로포스페이트, N,N'-카르보닐-디이미다졸, 2-에톡시-N-에톡시카르보닐-1,2-디히드로퀴놀린 (EEDQ), 트리페닐포스핀/테트라클로로-메탄, 4-(4,6-디메톡시[1.3.5]-트리아진-2-일)-4-메틸모르폴리늄 클로라이드 수화물, 비스(2-옥소-3-옥사졸리디닐)포스핀산 클로라이드 (BOP-Cl), 브로모-트리피롤리디노포스포늄헥사플루오로포스페이트 (PyBroP), 2-클로로-1,3-디메틸이미다졸리늄 클로라이드 (DMC) 또는 프로판포스폰산 무수물 (T3P)로 이루어진 비제한적 목록에서 선택될 수 있다.
U1이 할로겐 원자를 나타내는 경우에, 본 발명에 따른 방법 PXXI(1)은 유리하게는 산 결합제의 존재 하에 수행된다. 본 발명에 따른 방법 PXXI(1)을 수행하는 데 적합한 산 결합제는 각 경우에 이러한 반응에 통상적인 모든 무기 및 유기 염기이다. 알칼리 금속 탄산염, 예컨대 탄산세슘, 탄산나트륨, 탄산칼륨, 중탄산칼륨, 중탄산나트륨, 알칼리 토금속 아세테이트, 예컨대 아세트산나트륨, 아세트산칼륨, 아세트산칼슘 및 또한 3급 아민, 예컨대 트리메틸아민, 트리에틸아민, 디이소프로필에틸아민, 트리부틸아민, N,N-디메틸아닐린, N-메틸피페리딘, N,N-디메틸피리딘-4-아민, 디아자비시클로옥탄 (DABCO), 디아자비시클로-노넨 (DBN) 또는 디아자비시클로운데센 (DBU), 또는 방향족 염기, 예컨대 피리딘이 바람직하다.
U1이 C1-C6-알콕시 기를 나타내는 경우에, 본 발명에 따른 방법 PXXI(1)은, 임의로 루이스 산, 예컨대 트리메틸알루미늄의 존재 하에, 과량의 아민 성분을 사용하여 수행될 수 있다.
적절한 경우에, 방법 PXXI(1)은 염기의 존재 하에 및 적절한 경우에, 용매의 존재 하에, 바람직하게는 무수 조건 하에 수행될 수 있다.
방법 PXXI(1)을 수행하는 데 적합한 용매는 특별히 제한되지 않는다. 이들은, 화합물과 반응하거나 그와 임의의 특정한 상호작용을 나타내도록 화합물을 용해시키지 않는 한, 통상의 불활성 유기 용매일 수 있다. 임의로 할로겐화, 지방족, 지환족 또는 방향족 탄화수소, 예컨대 석유 에테르, 펜탄, 헥산, 헵탄, 시클로헥산, 메틸시클로헥산, 벤젠, 톨루엔, 크실렌, 데칼린, 이소파르™ E 또는 이소파르™ G, 클로로벤젠, 디클로로벤젠, 디클로로메탄, 클로로포름, 사염화탄소, 1,2-디클로로에탄 또는 트리클로로에탄; 에테르, 예컨대 디에틸 에테르, 디이소프로필 에테르, 메틸 tert-부틸 에테르, 메틸 tert-아밀 에테르, 디옥산, 테트라히드로푸란, 2-메틸테트라히드로푸란, 1,2-디메톡시에탄, 1,2-디에톡시에탄 또는 아니솔; 니트릴, 예컨대 아세토니트릴, 프로피오니트릴, n- 또는 이소-부티로니트릴 또는 벤조니트릴; 아미드, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸포름아닐리드, N-메틸피롤리돈 또는 헥사메틸인산 트리아미드; 우레아, 예컨대 1,3-디메틸-3,4,5,6-테트라히드로-2(1H)-피리미디논; 에스테르, 예컨대 메틸 아세테이트 또는 에틸 아세테이트, 술폭시드, 예컨대 디메틸 술폭시드 또는 술폰, 예컨대 술폴란; 및 그의 혼합물을 사용하는 것이 바람직하다.
방법 PXXI(1)은 아르곤 또는 질소 분위기와 같은 불활성 분위기에서 수행될 수 있다. 방법 PXXI(1)을 수행할 때, 화학식 (XXIII)의 화합물 1 몰당 1 몰 또는 과량의 화학식 (XXIII)의 화합물 및 1 내지 5 몰의 염기를 사용할 수 있다. 반응 성분을 다른 비로 사용하는 것이 또한 가능하다. 후처리는 공지된 방법에 의해 수행된다.
화학식 (XXIII)의 화합물은 상업적으로 입수가능하거나 널리 공지된 방법에 의해 제조될 수 있다.
U1이 히드록시 기를 나타내는 화학식 (XXII)의 화합물은 상업적으로 입수가능하거나, U1이 C1-C6-알콕시 기를 나타내는 화학식 (XXII)의 화합물로부터 널리 공지된 방법, 예컨대 염기성 가수분해에 의해 제조될 수 있거나 또는 공지된 방법에 의해 제조될 수 있다 (Beilstein J. Org. Chem. 2007, 3, No. 23).
U1이 할로겐을 나타내는 화학식 (XXII)의 화합물은 상업적으로 입수가능하거나 또는 U1이 히드록시 기를 나타내는 화학식 (XXII)의 화합물로부터 널리 공지된 방법에 의해 제조될 수 있다.
U1이 C1-C6-알콕시 기를 나타내는 화학식 (XXII)의 화합물은 U1이 히드록시 기를 나타내는 화학식 (XXII)의 화합물로부터 널리 공지된 방법에 의해 제조될 수 있다.
화학식 (XXI)의 화합물의 제조 - 방법 PXXI(2)
R4가 수소 원자 또는 C1-C6-알킬인 화학식 (XXI)의 화합물은 또한, 하기 반응식에 예시된 바와 같이 화학식 (XXIV)의 화합물의 디아조화에 이어서 방향족 치환을 수행하여 하기 화학식 (XXI)의 화합물을 제공하는 단계를 포함하는 방법 PXXI(2)에 의해 제조될 수 있다:
여기서 R4는 수소 원자 또는 C1-C6-알킬이고, U19는 아미노 기, 염소 원자 또는 브로민 원자이고, U20은 아미노 기, 염소 원자 또는 브로민 원자이고, 단 U19 또는 U19 중 적어도 1개는 아미노 기이다.
방법 PXXI(2)는 공지된 방법에 따라 수행될 수 있다 (문헌 [The Chemistry of diazonium and diazo groups; Saul Patai; Wiley-Interscience; 1978; 288-280 and 645-657; Account of Chemical Research (2018), 51, 496] 및 그에 인용된 참고문헌).
본원에 정의된 바와 같은 화학식 (XXIV)의 화합물은 하기 반응식에 예시된 바와 같이 화학식 (XXV)의 화합물을 탈보호 반응에 의해 탈보호시키는 단계를 포함하는 방법에 의해 제조될 수 있다:
여기서, R4는 수소 원자 또는 C1-C6-알킬이고, U21은 보호된 아미노 기, 염소 원자 또는 브로민 원자이고, U22는 보호된 아미노 기, 염소 원자 또는 브로민 원자이고, 단 U21 또는 U22 중 적어도 1개는 보호된 아미노 기이고, U19는 아미노 기, 염소 원자 또는 브로민 원자이고, U20은 아미노 기, 염소 원자 또는 브로민 원자이고, 단 U19 또는 U20 중 적어도 1개는 아미노 기이다.
아미노 기의 보호기의 예는 벤질 기, 4-메톡시벤질 기, 알릴 기, 비치환 또는 치환된 C1-C6-알킬술포닐, 트리플루오로메틸술포닐, 비치환 또는 치환된 페닐술포닐, 비치환 또는 치환된 C1-C6-알콕시카르보닐, 비치환 또는 치환된 벤질옥시카르보닐, 알릴옥시카르보닐, 아세틸 기 또는 트리플루오로아세틸 기를 포함한다.
탈보호 방법은 보호기를 제거하기 위한 공지된 방법에 따라 수행될 수 있다 (Greene's Protective Groups in Organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194). 예를 들어, tert-부톡시카르보닐 및 벤질옥시카르보닐 보호기를 산성 매질 (예를 들어 염산 또는 트리플루오로아세트산을 사용함) 중에서 제거할 수 있다. 벤질 보호기는 촉매 (예를 들어 활성 탄소 상의 팔라듐)의 존재 하에 수소를 사용하여 가수소분해로 제거할 수 있다. 트리플루오로아세틸 기를 염기성 매질 (예를 들어 탄산칼륨 또는 수산화리튬을 사용함) 중에서 제거할 수 있다.
방법 PXXI(1)과 관련하여 기재된 바와 같은 조건에서 화학식 (XXIV)의 화합물은 또한 화학식 (XXVI)의 화합물로부터 제조될 수 있고, 화학식 (XXV)의 화합물은 화학식 (XXVII)의 화합물을 화학식 (XXIII)의 화합물과 반응시킴으로써 제조될 수 있다:
여기서 U19, U20, U21 및 U22는 본원에 정의된 바와 같고, U1는 할로겐 원자, 히드록시 기 또는 C1-C6-알콕시 기이다.
화학식 (XXVI)의 화합물 및 화학식 (XXVII)의 화합물은 상업적으로 입수가능하거나 또는 화학식 (XXII)의 화합물을 제조하기 위해 개시된 것과 유사한 반응 조건을 사용하여 널리 공지된 방법에 의해 제조될 수 있다.
화학식 (XXI)의 화합물의 제조 - 방법 PXXI(3)
화학식 (XXI)의 화합물은 또한 하기 반응식에 예시된 바와 같이 화학식 (XXVIII)의 화합물로부터 방법 PXXI(3)에 의해 제조될 수 있다:
여기서, R4는 수소 원자 또는 C1-C6-알킬이고, R3은 R1 및 R2와 상이하고 플루오린 원자 또는 염소 원자이다.
방법 PXXI(3)은 공지된 방법에 따라 수행될 수 있다 (문헌 [The Chemistry of diazonium and diazo groups; Saul Patai; Wiley-Interscience; 1978; 288-280 and 645-657; Account of Chemical Research (2018), 51, 496] 및 그에 인용된 참고문헌).
본원에 정의된 바와 같은 화학식 (XXVIII)의 화합물은 하기 반응식에 예시된 바와 같이 화학식 (XXIX)의 화합물을 탈보호 반응에 의해 탈보호시키는 단계를 포함하는 방법에 의해 제조될 수 있다:
여기서 R4는 수소 원자 또는 C1-C6-알킬이고, U23은 보호된 아미노 기이다.
아미노 기의 보호기의 예는 벤질 기, 4-메톡시벤질 기, 알릴 기, 비치환 또는 치환된 C1-C6-알킬술포닐, 트리플루오로메틸술포닐, 비치환 또는 치환된 페닐술포닐, 비치환 또는 치환된 C1-C6-알콕시카르보닐, 비치환 또는 치환된 벤질옥시카르보닐, 알릴옥시카르보닐, 아세틸 기 또는 트리플루오로아세틸 기를 포함한다.
탈보호 방법은 보호기를 제거하기 위한 공지된 방법에 따라 수행될 수 있다 (Greene's Protective Groups in Organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194). 예를 들어, tert-부톡시카르보닐 및 벤질옥시카르보닐 보호기를 산성 매질 (예를 들어 염산 또는 트리플루오로아세트산을 사용함) 중에서 제거할 수 있다. 벤질 보호기는 촉매 (예를 들어 활성 탄소 상의 팔라듐)의 존재 하에 수소를 사용하여 가수소분해로 제거할 수 있다. 트리플루오로아세틸 기를 염기성 매질 (예를 들어 탄산칼륨 또는 수산화리튬을 사용함) 중에서 제거할 수 있다.
방법 PXXI(1)과 관련하여 기재된 바와 같은 조건에서 화학식 (XXVIII)의 화합물은 또한 화학식 (XXX)의 화합물로부터 제조될 수 있고, 화학식 (XXIX)의 화합물은 화학식 (XXXI)의 화합물로부터 화학식 (XXIII)의 화합물과 반응시켜 제조될 수 있다:
여기서 U23은 본원에 정의되어 있고, U1은 할로겐 원자, 히드록시 기 또는 C1-C6-알콕시 기이다.
화학식 (XXX)의 화합물 및 화학식 (XXXI)의 화합물은 상업적으로 입수가능하거나 또는 화학식 (XXII)의 화합물을 제조하기 위해 개시된 것과 유사한 반응 조건을 사용하여 널리 공지된 방법에 의해 제조될 수 있다.
화학식 (XXI)의 화합물의 제조 - 방법 PXXI(4)
R4가 수소 원자 또는 C1-C6-알킬인 화학식 (XXI)의 화합물은 하기 반응식에 의해 예시된 바와 같이 화학식 (XXXII)의 화합물을 화학식 (XXXIII)의 화합물 또는 그의 염 중 1종과 반응시키는 단계를 포함하는 방법 PXXI(4)에 의해 제조될 수 있다:
여기서 R4는 수소 원자 또는 C1-C6-알킬이고, U2는 브로민 원자, 아이오딘 원자, 메실레이트 기, 토실레이트 기 또는 트리플레이트 기이고, U3은 붕소 유도체, 예컨대 보론산, 보론산 에스테르 유도체, 칼륨 트리플루오로보레이트 유도체 또는 할로게노마그네슘 또는 할로게노아연과 같은 1 내지 2개의 리간드에 의해 착물화될 수 있는 할로게노금속이다.
방법 PXXI(4)는 전이 금속 촉매 예컨대 팔라듐의 존재 하에 및 적절한 경우에 포스핀 리간드 또는 N-헤테로시클릭 카르벤 리간드의 존재 하에, 적절한 경우에, 염기의 존재 하에 및 적절한 경우에, 용매의 존재 하에, 공지된 방법에 따라 수행될 수 있다 (WO2012054721, 문헌 [Angewandte Chemie International Edition (2017), 56, 1581, Angewandte Chemie International Edition (2017), 56, 7078] 및 그에 인용된 참고문헌).
방법 PXXI(4)는 촉매, 예컨대 금속 염 또는 착물의 존재 하에 수행될 수 있다. 이러한 목적에 적합한 금속 유도체는 전이 금속 촉매, 예컨대 팔라듐이다. 이러한 목적에 적합한 금속 염 또는 착물은 예를 들어 염화팔라듐, 아세트산팔라듐, 테트라키스(트리페닐포스핀)팔라듐(0), 비스(디벤질리덴아세톤)팔라듐(0), 트리스(디벤질리덴아세톤)디팔라듐(0), 비스(트리페닐포스핀)팔라듐(II) 디클로라이드, [1,1'-비스(디페닐포스피노)페로센]디클로로팔라듐(II), 비스(신나밀)디클로로디팔라듐(II), 비스(알릴)-디클로로디팔라듐(II), [1,1'-비스(디-tert-부틸포스피노)페로센]디클로로팔라듐(II), 디-μ-아이오도비스(트리-tert-부틸포스피노)디팔라듐(I) 또는 디-μ-브로모비스(트리-tert-부틸포스피노)디팔라듐(I)이다.
또한, 반응물에 팔라듐 염 및 리간드 또는 염, 예컨대 트리에틸포스핀, 트리-tert-부틸포스핀, 트리-tert-부틸포스포늄 테트라플루오로보레이트, 트리시클로헥실포스핀, 2-(디시클로헥실포스피노)비페닐, 2-(디-tert-부틸포스피노)비페닐, 2-(디시클로헥실포스피노)-2'-(N,N-디메틸아미노)비페닐, 2-(tert-부틸포스피노)-2'-(N,N-디메틸아미노)비페닐, 2-디-tert-부틸포스피노-2',4',6'-트리이소프로필비페닐 2-디시클로헥실포스피노-2',4',6'-트리이소프로필비페닐, 2-디시클로헥실포스피노-2,6'-디메톡시비페닐, 2-디시클로헥실포스피노-2',6'-디이소프로폭시비페닐, 트리페닐-포스핀, 트리스-(o-톨릴)포스핀, 소듐 3-(디페닐포스피노)벤젠술포네이트, 트리스-2-(메톡시-페닐)포스핀, 2,2'-비스(디페닐포스피노)-1,1'-비나프틸, 1,4-비스(디페닐포스피노)부탄, 1,2-비스(디페닐포스피노)에탄, 1,4-비스(디시클로헥실포스피노)부탄, 1,2-비스(디시클로헥실포스피노)-에탄, 2-(디시클로헥실포스피노)-2'-(N,N-디메틸아미노)-비페닐, 1,1'-비스(디페닐포스피노)-페로센, (R)-(-)-1-[(S)-2-디페닐-포스피노)페로세닐]에틸디시클로헥실포스핀, 트리스-(2,4-tert-부틸-페닐)포스파이트, 디(1-아다만틸)-2-모르폴리노페닐포스핀 또는 1,3-비스(2,4,6-트리메틸페닐)이미다졸륨 클로라이드를 개별적으로 첨가함으로써 반응 혼합물 중에서 팔라듐 착물을 생성하는 것이 가능하다.
스트렘 케미칼스(Strem Chemicals)에 의한 "유기 합성을 위한 금속 촉매(Metal Catalysts for Organic Synthesis)" 또는 스트렘 케미칼스에 의한 "인 리간드 및 화합물(Phosphorous Ligands and Compounds)"과 같은 상업 카탈로그로부터 적절한 촉매 및/또는 리간드를 선택하는 것이 또한 유리하다.
방법 PXXI(4)를 수행하는 데 적합한 염기는 이러한 반응에 통상적인 무기 및 유기 염기일 수 있다. 알칼리 토금속 또는 알칼리 금속 수산화물, 예컨대 수산화나트륨, 수산화칼슘, 수산화칼륨 또는 다른 수산화암모늄 유도체; 알칼리 토금속, 알칼리 금속 또는 플루오린화암모늄, 예컨대 플루오린화칼륨, 플루오린화세슘 또는 테트라부틸암모늄 플루오라이드; 알칼리 토금속 또는 알칼리 금속 탄산염, 예컨대 탄산나트륨, 탄산칼륨, 중탄산칼륨, 중탄산나트륨 또는 탄산세슘; 알칼리 금속 또는 알칼리 토금속 아세테이트, 예컨대 아세트산나트륨, 아세트산리튬, 아세트산칼륨 또는 아세트산칼슘; 알칼리 금속 또는 알칼리 토금속 포스페이트, 예컨대 인산삼칼륨 알칼리; 알칼리 금속 알콜레이트, 예컨대 포타슘 tert-부톡시드 또는 소듐 tert-부톡시드; 3급 아민, 예컨대 트리메틸아민, 트리에틸아민, 트리부틸아민, N,N-디메틸아닐린, N,N-디시클로헥실메틸아민, N,N-디이소프로필에틸아민, N-메틸피페리딘, N,N-디메틸아미노피리딘, 디아자비시클로옥탄 (DABCO), 디아자비시클로노넨 (DBN) 또는 디아자비시클로운데센 (DBU); 및 또한 방향족 염기, 예컨대 피리딘, 피콜린, 루티딘 또는 콜리딘을 사용하는 것이 바람직하다.
방법 PXXI(4)를 수행하는 데 적합한 용매는 통상적인 불활성 유기 용매일 수 있다. 임의로 할로겐 원자함유 지방족, 지환족 또는 방향족 탄화수소, 예컨대 석유 에테르, 펜탄, 헥산, 헵탄, 시클로헥산, 메틸시클로헥산, 벤젠, 톨루엔, 크실렌 또는 데칼린; 클로로벤젠, 디클로로벤젠, 디클로로메탄, 클로로포름, 사염화탄소, 디클로로에탄 또는 트리클로로에탄; 에테르, 예컨대 디에틸 에테르, 디이소프로필 에테르, 메틸 tert-부틸 에테르, 메틸 tert-아밀 에테르, 디옥산, 테트라히드로푸란, 2-메틸테트라히드로푸란, 1,2-디메톡시에탄, 1,2-디에톡시에탄 또는 아니솔; 니트릴, 예컨대 아세토니트릴, 프로피오니트릴, n- 또는 이소-부티로니트릴 또는 벤조니트릴; 아미드, 예컨대 N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸포름아닐리드, N-메틸피롤리돈 또는 헥사메틸인산 트리아미드; 우레아, 예컨대 1,3-디메틸-3,4,5,6-테트라히드로-2(1H)-피리미디논; 에스테르, 예컨대 메틸 아세테이트 또는 에틸 아세테이트, 술폭시드, 예컨대 디메틸 술폭시드 또는 술폰, 예컨대 술폴란; 및 그의 혼합물을 사용하는 것이 바람직하다.
공용매, 예컨대 물 또는 알콜, 예컨대 메탄올, 에탄올, 프로판올, 이소프로판올 또는 tert-부탄올을 사용하여 방법 PXXI(4)를 수행하는 것이 또한 유리할 수 있다.
방법 PXXI(4)는 불활성 분위기, 예컨대 아르곤 또는 질소 분위기에서 수행할 수 있다. 방법 PXXI(4)를 수행할 때, 화학식 (XXXII)의 화합물 1 몰당 1 몰 또는 과량의 화학식 (XXXIII)의 화합물 및 1 내지 5 몰의 염기 및 0.01 내지 20 몰 퍼센트의 팔라듐 착물을 사용할 수 있다. 반응 성분을 다른 비로 사용하는 것이 또한 가능하다. 후처리는 공지된 방법에 의해 수행된다.
화학식 (XXXIII)의 화합물은 상업적으로 입수가능하거나 널리 공지된 방법에 의해 제조될 수 있다.
화학식 (XXXII)의 화합물은 방법 PXXI(1)과 관련하여 기재된 바와 같은 조건에서 화학식 (XXXIV)의 화합물을 화학식 (XXIII)의 화합물과 반응시킴으로써 제조될 수 있다:
여기서 U2 및 U1은 본원에 정의된 바와 같다.
U2가 염소 원자, 브로민 원자 또는 아이오딘 원자인 화학식 (XXXIV)의 화합물은 상업적으로 입수가능하거나 또는 화학식 (XXII)의 화합물을 제조하기 위해 개시된 것과 유사한 반응 조건을 사용하여 널리 공지된 방법에 의해 제조될 수 있다.
U2가 메실레이트 기, 토실레이트 기 또는 트리플레이트 기인 화학식 (XXXIV)의 화합물은 U2 위치에서 히드록시 기를 보유하는 상응하는 화합물로부터 널리 공지된 방법에 의해 제조될 수 있다.
화학식 (XXI)의 화합물의 제조 - 방법 PXXI(5)
R4가 수소 원자 또는 C1-C6-알킬인 화학식 (XXI)의 화합물은 하기 반응식에 예시된 바와 같이 플루오린화 반응에 의해 방법 PXXI(5)에 의해 제조될 수 있다:
여기서 R4는 수소 원자 또는 C1-C6-알킬이다.
방법 PXXI(5)는 공지된 방법에 따라 수행될 수 있다 (문헌 [Journal of the American Chemical Society 2011, 133, 11482 and Organic Process Research & Development 2014, 18, 1041]).
본 발명에 따른 화합물은 상기 기재된 방법에 따라 제조될 수 있다. 그럼에도 불구하고, 숙련된 작업자는, 그의 일반적 지식 및 이용가능한 간행물에 기초하여, 합성하고자 하는 본 발명에 따른 각각의 화합물의 세부사항에 따라 이들 방법을 적합화할 수 있을 것으로 이해될 것이다.
본원에 개시된 중간체는 박테리아 및/또는 진균을 방제하는 데 효율적일 수 있다.
화학식 (III)의 화합물의 제조를 위한 중간체
본 발명은 화학식 (III)의 화합물의 제조를 위한 중간체에 관한 것이다.
달리 나타내지 않는 한, 하기에서, R1, R2 및 R3은 화학식 (III)의 화합물에 대해 상기 제공된 것과 동일한 의미를 갖는다.
하기 화학식 (XXI)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고; R4는 수소 원자 또는 C1-C6-알킬이다.
하기 화학식 (XXIIa)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고;
단 R1 및 R2가 염소 원자인 경우에 R3은 염소 원자가 아니고;
U1a는 히드록시 기 또는 C1-C6-알콕시 기이고;
단 화학식 (XXIIa)의 화합물은 하기를 나타내지 않는다:
- 메틸 4,5-디클로로-3-플루오로티오펜-2-카르복실레이트 [2166596-88-7],
- 4,5-디클로로-3-플루오로티오펜-2-카르복실산 [2166596-87-6],
- 에틸 4,5-디브로모-3-플루오로티오펜-2-카르복실레이트 [2260624-98-2],
- 4,5-디브로모-3-플루오로티오펜-2-카르복실산 [1628447-64-2],
- 메틸 4,5-디브로모-3-클로로티오펜-2-카르복실레이트 [1501789-47-4],
- 4,5-디브로모-3-아이오도티오펜-2-카르복실산 [854626-46-3],
- 4,5-디브로모-3-클로로티오펜-2-카르복실산 [503308-99-4],
- 에틸 4,5-디브로모-3-클로로티오펜-2-카르복실레이트 [503308-98-3],
- 메틸 4,5-디브로모-3-플루오로티오펜-2-카르복실레이트 [395664-58-1],
- tert-부틸 3,4,5-트리브로모티오펜-2-카르복실레이트 [62224-27-5],
- 에틸 3,4,5-트리브로모티오펜-2-카르복실레이트 [54113-44-9],
- 3,4,5-트리브로모티오펜-2-카르복실산 [53317-05-8],
- 메틸 3,4,5-트리브로모티오펜-2-카르복실레이트 [24647-80-1],
- 에틸 4,5-디브로모-3-메틸티오펜-2-카르복실레이트 [2088257-63-8],
- 4,5-디클로로-3-메틸티오펜-2-카르복실산 [854626-34-9],
- 4,5-디브로모-3-메틸티오펜-2-카르복실산 [854626-32-7],
- 메틸 4,5-디클로로-3-메틸티오펜-2-카르복실레이트 [854626-27-0], 및
- 메틸 4,5-디브로모-3-메틸티오펜-2-카르복실레이트 [648412-53-7].
하기 화학식 (XXIVa) 및 (XXIVb)의 화합물:
여기서
R1 또는 R2는 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고;
R4는 수소 원자 또는 C1-C6-알킬이다.
하기 화학식 (XXVa) 및 (XXVb)의 화합물이 제공된다:
여기서
R1 또는 R2는 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고;
R4는 수소 원자 또는 C1-C6-알킬이고;
V는 벤질 기, 4-메톡시벤질 기, 알릴 기, 비치환 또는 치환된 C1-C6-알콕시카르보닐, 비치환 또는 치환된 벤질옥시카르보닐, 알릴옥시카르보닐, 아세틸 기 또는 트리플루오로아세틸 기이다.
하기 화학식 (XXVIa) 및 (XXVIb)의 화합물이 제공된다:
여기서
R1 또는 R2는 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고;
U1a는 히드록시 기 또는 C1-C6-알콕시 기이고,
단 화학식 (XXVIa)의 화합물은 하기를 나타내지 않고:
- 에틸 5-아미노-4-브로모-3-메틸티오펜-2-카르복실레이트 [851443-15-7];
단 화학식 (XXVIb)의 화합물은 하기를 나타내지 않는다:
- 에틸 4-아미노-3,5-디브로모티오펜-2-카르복실레이트 [1394375-09-7].
하기 화학식 (XXVIIa) 및 (XXVIIb)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고;
V는 벤질 기, 4-메톡시벤질 기, 알릴 기, 비치환 또는 치환된 C1-C6-알콕시카르보닐, 비치환 또는 치환된 벤질옥시카르보닐, 알릴옥시카르보닐, 아세틸 기 또는 트리플루오로아세틸 기이고;
U1a는 히드록시 기 또는 C1-C6-알콕시 기이고,
단 화학식 (XXVIIa)의 화합물은 하기를 나타내지 않는다:
- 에틸 5-아세트아미도-4-브로모-3-메틸티오펜-2-카르복실레이트 [851444-63-8].
하기 화학식 (XXVIII) 및 (XXIXa)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R4는 수소 원자 또는 C1-C6-알킬이고;
V는 벤질 기, 4-메톡시벤질 기, 알릴 기, 비치환 또는 치환된 C1-C6-알콕시카르보닐, 비치환 또는 치환된 벤질옥시카르보닐, 알릴옥시카르보닐, 아세틸 기 또는 트리플루오로아세틸 기이다.
하기 화학식 (XXXa) 및 (XXXIa)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
V는 벤질 기, 4-메톡시벤질 기, 알릴 기, 비치환 또는 치환된 C1-C6-알콕시카르보닐, 비치환 또는 치환된 벤질옥시카르보닐, 알릴옥시카르보닐, 아세틸 기 또는 트리플루오로아세틸 기이고;
U1a는 히드록시 기 또는 C1-C6-알콕시 기이고,
단 화학식 (XXXa)의 화합물은 하기를 나타내지 않고:
- 메틸 3-아미노-4,5-디클로로티오펜-2-카르복실레이트 [1621488-35-4],
단 화학식 (XXXIa)의 화합물은 하기를 나타내지 않는다:
- 3-아세트아미도-4,5-디클로로티오펜-2-카르복실산 [2090448-72-7],
- 메틸 3-아세트아미도-4,5-디클로로티오펜-2-카르복실레이트 [632356-39-9], 및
- 메틸 4,5-디클로로-3-[(메톡시카르보닐)아미노]티오펜-2-카르복실레이트 [35707-28-9].
하기 화학식 (XXXIIa)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R4는 수소 원자 또는 C1-C6-알킬이고;
U2a는 브로민 원자, 아이오딘 원자, 메실레이트 기, 토실레이트 기 또는 트리플레이트 기이고, 단 R1 및 R2가 브로민 원자인 경우에, U2a는 브로민 원자가 아니다.
하기 화학식 (XXXIVa)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
U2b는 메실레이트 기, 토실레이트 기 또는 트리플레이트 기이고;
U1a는 히드록시 기 또는 C1-C6-알콕시 기이다.
하기 화학식 (XXXV)의 화합물이 제공된다:
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R4는 수소 원자 또는 C1-C6-알킬이다.
개시된 중간체는 박테리아 및/또는 진균을 방제하는 데 효율적일 수 있다.
조성물 및 제제
본 발명은 추가로 상기 본원에 개시된 바와 같은 화학식 (III)의 1종 이상의 화합물 및 그의 임의의 혼합물을 포함하는 조성물, 특히 크산토모나스 속의 박테리아에 의해 유발된 식물 질병을 방제하기 위한 조성물에 관한 것이다.
조성물은 전형적으로 화학식 (III)의 1종 이상의 화합물 및 1종 이상의 농업상 적합한 보조제, 예를 들어 담체(들) 및/또는 계면활성제(들)를 포함한다.
담체는 일반적으로 불활성인 고체 또는 액체, 천연 또는 합성, 유기 또는 무기 물질이다. 담체는 일반적으로 예를 들어 식물, 식물 부분 또는 종자에 대한 화합물의 적용을 개선시킨다. 적합한 고체 담체의 예는 암모늄 염, 천연 암분, 예컨대 카올린, 점토, 활석, 백악, 석영, 아타풀자이트, 몬모릴로나이트 및 규조토 및 합성 암분, 예컨대 미분된 실리카, 알루미나 및 실리케이트를 포함하나 이에 제한되지는 않는다. 과립 제조에 전형적으로 유용한 고체 담체의 예는 분쇄 및 분획화된 천연 암석, 예컨대 방해석, 대리석, 부석, 세피올라이트 및 돌로마이트, 무기 및 유기 분의 합성 과립, 및 유기 물질, 예컨대 종이, 톱밥, 코코넛 쉘, 옥수수 속대 및 담배 자루의 과립을 포함하나 이에 제한되지는 않는다. 적합한 액체 담체의 예는 물, 유기 용매 및 그의 조합을 포함하나 이에 제한되지는 않는다. 적합한 용매의 예는, 예를 들어 방향족 및 비방향족 탄화수소 (예컨대 시클로헥산, 파라핀, 알킬벤젠, 크실렌, 톨루엔 알킬나프탈렌, 염소화 방향족 또는 염소화 지방족 탄화수소 예컨대 클로로벤젠, 클로로에틸렌 또는 메틸렌 클로라이드), 알콜 및 폴리올 (또한 임의로 치환, 에테르화 및/또는 에스테르화될 수 있음, 예컨대 부탄올 또는 글리콜), 케톤 (예컨대 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤 또는 시클로헥사논), 에스테르 (지방 및 오일 포함) 및 (폴리)에테르, 비치환 및 치환된 아민, 아미드 (예컨대 디메틸포름아미드), 락탐 (예컨대 N-알킬피롤리돈) 및 락톤, 술폰 및 술폭시드 (예컨대 디메틸 술폭시드)의 부류로부터의 극성 및 비극성 유기 화학 액체를 포함한다. 담체는 또한 액화된 기체상 증량제, 즉 표준 온도에서 및 표준 압력 하에 기체상인 액체, 예를 들어 에어로졸 추진제, 예컨대 할로탄화수소, 부탄, 프로판, 질소 및 이산화탄소일 수 있다. 담체의 양은 전형적으로 조성물의 1 내지 99.99 중량%, 바람직하게는 5 내지 99.9 중량%, 보다 바람직하게는 10 내지 99.5 중량%, 가장 바람직하게는 20 내지 99 중량%의 범위이다.
계면활성제는 이온성 (양이온성 또는 음이온성) 또는 비이온성 계면활성제, 예컨대 이온성 또는 비이온성 유화제(들), 거품 형성제(들), 분산제(들), 습윤제(들) 및 그의 임의의 혼합물일 수 있다. 적합한 계면활성제의 예는 폴리아크릴산의 염, 리그노술폰산의 염, 페놀술폰산 또는 나프탈렌술폰산의 염, 에틸렌 및/또는 프로필렌 옥시드와 지방 알콜, 지방산 또는 지방 아민의 중축합물 (폴리옥시에틸렌 지방산 에스테르, 폴리옥시에틸렌 지방 알콜 에테르, 예를 들어 알킬아릴 폴리글리콜 에테르), 치환된 페놀 (바람직하게는 알킬페놀 또는 아릴페놀), 술포숙신산 에스테르의 염, 타우린 유도체 (바람직하게는 알킬 타우레이트), 폴리에톡실화 알콜 또는 페놀의 인산 에스테르, 폴리올의 지방 에스테르, 및 술페이트, 술포네이트, 포스페이트를 함유하는 화합물의 유도체 (예를 들어, 알킬술포네이트, 알킬 술페이트, 아릴술포네이트) 및 단백질 가수분해물, 리그노술파이트 폐액 및 메틸셀룰로스를 포함하나 이에 제한되지는 않는다. 계면활성제는 전형적으로 본 발명의 화합물 및/또는 담체가 물에 불용성이고 적용이 물로 이루어지는 경우에 사용된다. 이어서 계면활성제의 양은 전형적으로 조성물의 5 내지 40 중량%의 범위이다.
적합한 보조제의 추가의 예는 발수제, 건조제, 결합제 (접착제, 점착제, 고정제, 예컨대 카르복시메틸셀룰로스, 분말, 과립 또는 라텍스 형태의 천연 및 합성 중합체, 예컨대 아라비아 검, 폴리비닐 알콜 및 폴리비닐 아세테이트, 천연 인지질, 예컨대 세팔린 및 레시틴 및 합성 인지질, 폴리비닐피롤리돈 및 틸로스), 증점제, 안정화제 (예를 들어 저온 안정화제, 보존제, 항산화제, 광 안정화제 또는 화학적 및/또는 물리적 안정성을 개선시키는 다른 작용제), 염료 또는 안료 (예컨대 무기 안료, 예를 들어 산화철, 산화티타늄 및 프러시안 블루; 유기 염료, 예를 들어 알리자린, 아조 및 금속 프탈로시아닌 염료), 소포제 (예를 들어 실리콘 소포제 및 스테아르산마그네슘), 보존제 (예를 들어 디클로로펜 및 벤질 알콜 헤미포르말), 2차 증점제 (셀룰로스 유도체, 아크릴산 유도체, 크산탄, 개질된 점토 및 미분된 실리카), 점착제, 지베렐린 및 가공 보조제, 미네랄 및 식물성 오일, 퍼퓸, 왁스, 영양소 (미량 영양소, 예컨대 철, 망가니즈, 붕소, 구리, 코발트, 몰리브데넘 및 아연의 염 포함), 보호 콜로이드, 요변성 물질, 침투제, 봉쇄제 및 착물 형성제를 포함한다.
보조제의 선택은 본 발명의 화합물의 의도된 적용 방식 및/또는 물리적 특성과 관련된다. 또한, 보조제는 조성물 또는 그로부터 제조된 사용 형태에 특정한 특성 (기술적, 물리적 및/또는 생물학적 특성)을 부여하도록 선택될 수 있다. 보조제의 선택은 조성물을 구체적 필요에 따라 맞춤화할 수 있게 한다.
본 발명의 조성물은 임의의 통상적인 형태, 예컨대 용액 (예를 들어 수용액), 에멀젼, 습윤성 분말, 수- 및 오일-기재 현탁액, 분말, 산분, 페이스트, 가용성 분말, 가용성 과립, 살포용 과립, 유현탁액 농축물, 본 발명의 화합물(들)로 함침된 천연 또는 합성 생성물, 비료 및 또한 중합체 물질 중의 마이크로캡슐로 존재할 수 있다. 본 발명의 화합물(들)은 현탁, 유화 또는 용해된 형태로 존재할 수 있다.
본 발명의 조성물은 최종 사용자에게 즉시 사용가능한 제제로서 제공될 수 있으며, 즉 조성물은 분무 또는 살분 장치와 같은 적합한 장치에 의해 식물 또는 종자에 직접 적용될 수 있다. 대안적으로, 조성물은 사용 전에, 바람직하게는 물로 희석되어야 하는 농축물의 형태로 최종 사용자에게 제공될 수 있다.
본 발명의 조성물은 통상적인 방식으로, 예를 들어 본 발명의 화합물(들)을 1종 이상의 적합한 보조제, 예컨대 본원에 상기 개시된 것과 혼합함으로써 제조될 수 있다.
본 발명에 따른 조성물은 일반적으로 0.01 내지 99 중량%, 0.05 내지 98 중량%, 바람직하게는 0.1 내지 95 중량%, 보다 바람직하게는 0.5 내지 90 중량%, 가장 바람직하게는 1 내지 80 중량%의 본 발명의 화합물(들)을 함유한다. 조성물이 2종 이상의 본 발명의 화합물을 포함하는 것이 가능하다. 이러한 경우에 약술된 범위는 본 발명의 화합물의 총량을 지칭한다.
혼합물/조합물
본 발명의 화합물(들) 및 조성물은 살진균제, 살박테리아제, 살진드기제, 살선충제, 살곤충제, 제초제, 비료, 성장 조절제, 완화제 및/또는 신호화학물질과 같은 다른 활성 성분과 혼합될 수 있다. 이는 활성 스펙트럼을 넓히거나 또는 내성의 발생을 방지하도록 할 수 있다. 공지된 살진균제, 살곤충제, 살진드기제, 살선충제 및 살박테리아제의 예는 문헌 [the Pesticide Manual, 17th Edition]에 개시되어 있다.
본 발명의 화합물(들) 및 조성물과 혼합될 수 있는 특히 바람직한 살진균제의 예는 하기와 같다:
1) 에르고스테롤 생합성 억제제, 예를 들어 (1.001) 시프로코나졸, (1.002) 디페노코나졸, (1.003) 에폭시코나졸, (1.004) 펜헥사미드, (1.005) 펜프로피딘, (1.006) 펜프로피모르프, (1.007) 펜피라자민, (1.008) 플루퀸코나졸, (1.009) 플루트리아폴, (1.010) 이마잘릴, (1.011) 이마잘릴 술페이트, (1.012) 이프코나졸, (1.013) 메트코나졸, (1.014) 미클로부타닐, (1.015) 파클로부트라졸, (1.016) 프로클로라즈, (1.017) 프로피코나졸, (1.018) 프로티오코나졸, (1.019) 피르이속사졸, (1.020) 스피록사민, (1.021) 테부코나졸, (1.022) 테트라코나졸, (1.023) 트리아디메놀, (1.024) 트리데모르프, (1.025) 트리티코나졸, (1.026) (1R,2S,5S)-5-(4-클로로벤질)-2-(클로로메틸)-2-메틸-1-(1H-1,2,4-트리아졸-1-일메틸)시클로펜탄올, (1.027) (1S,2R,5R)-5-(4-클로로벤질)-2-(클로로메틸)-2-메틸-1-(1H-1,2,4-트리아졸-1-일메틸)시클로펜탄올, (1.028) (2R)-2-(1-클로로시클로프로필)-4-[(1R)-2,2-디클로로시클로프로필]-1-(1H-1,2,4-트리아졸-1-일)부탄-2-올, (1.029) (2R)-2-(1-클로로시클로프로필)-4-[(1S)-2,2-디클로로시클로프로필]-1-(1H-1,2,4-트리아졸-1-일)부탄-2-올, (1.030) (2R)-2-[4-(4-클로로페녹시)-2-(트리플루오로메틸)페닐]-1-(1H-1,2,4-트리아졸-1-일)프로판-2-올, (1.031) (2S)-2-(1-클로로시클로프로필)-4-[(1R)-2,2-디클로로시클로프로필]-1-(1H-1,2,4-트리아졸-1-일)부탄-2-올, (1.032) (2S)-2-(1-클로로시클로프로필)-4-[(1S)-2,2-디클로로시클로프로필]-1-(1H-1,2,4-트리아졸-1-일)부탄-2-올, (1.033) (2S)-2-[4-(4-클로로페녹시)-2-(트리플루오로메틸)페닐]-1-(1H-1,2,4-트리아졸-1-일)프로판-2-올, (1.034) (R)-[3-(4-클로로-2-플루오로페닐)-5-(2,4-디플루오로페닐)-1,2-옥사졸-4-일](피리딘-3-일)메탄올, (1.035) (S)-[3-(4-클로로-2-플루오로페닐)-5-(2,4-디플루오로페닐)-1,2-옥사졸-4-일](피리딘-3-일)메탄올, (1.036) [3-(4-클로로-2-플루오로페닐)-5-(2,4-디플루오로페닐)-1,2-옥사졸-4-일](피리딘-3-일)메탄올, (1.037) 1-({(2R,4S)-2-[2-클로로-4-(4-클로로페녹시)페닐]-4-메틸-1,3-디옥솔란-2-일}메틸)-1H-1,2,4-트리아졸, (1.038) 1-({(2S,4S)-2-[2-클로로-4-(4-클로로페녹시)페닐]-4-메틸-1,3-디옥솔란-2-일}메틸)-1H-1,2,4-트리아졸, (1.039) 1-{[3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-1H-1,2,4-트리아졸-5-일 티오시아네이트, (1.040) 1-{[rel(2R,3R)-3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-1H-1,2,4-트리아졸-5-일 티오시아네이트, (1.041) 1-{[rel(2R,3S)-3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-1H-1,2,4-트리아졸-5-일 티오시아네이트, (1.042) 2-[(2R,4R,5R)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.043) 2-[(2R,4R,5S)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.044) 2-[(2R,4S,5R)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.045) 2-[(2R,4S,5S)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.046) 2-[(2S,4R,5R)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.047) 2-[(2S,4R,5S)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.048) 2-[(2S,4S,5R)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.049) 2-[(2S,4S,5S)-1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.050) 2-[1-(2,4-디클로로페닐)-5-히드록시-2,6,6-트리메틸헵탄-4-일]-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.051) 2-[2-클로로-4-(2,4-디클로로페녹시)페닐]-1-(1H-1,2,4-트리아졸-1-일)프로판-2-올, (1.052) 2-[2-클로로-4-(4-클로로페녹시)페닐]-1-(1H-1,2,4-트리아졸-1-일)부탄-2-올, (1.053) 2-[4-(4-클로로페녹시)-2-(트리플루오로메틸)페닐]-1-(1H-1,2,4-트리아졸-1-일)부탄-2-올, (1.054) 2-[4-(4-클로로페녹시)-2-(트리플루오로메틸)페닐]-1-(1H-1,2,4-트리아졸-1-일)펜탄-2-올, (1.055) 메펜트리플루코나졸, (1.056) 2-{[3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.057) 2-{[rel(2R,3R)-3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.058) 2-{[rel(2R,3S)-3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-2,4-디히드로-3H-1,2,4-트리아졸-3-티온, (1.059) 5-(4-클로로벤질)-2-(클로로메틸)-2-메틸-1-(1H-1,2,4-트리아졸-1-일메틸)시클로펜탄올, (1.060) 5-(알릴술파닐)-1-{[3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-1H-1,2,4-트리아졸, (1.061) 5-(알릴술파닐)-1-{[rel(2R,3R)-3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-1H-1,2,4-트리아졸, (1.062) 5-(알릴술파닐)-1-{[rel(2R,3S)-3-(2-클로로페닐)-2-(2,4-디플루오로페닐)옥시란-2-일]메틸}-1H-1,2,4-트리아졸, (1.063) N'-(2,5-디메틸-4-{[3-(1,1,2,2-테트라플루오로에톡시)페닐]술파닐}페닐)-N-에틸-N-메틸이미도포름아미드, (1.064) N'-(2,5-디메틸-4-{[3-(2,2,2-트리플루오로에톡시)페닐]술파닐}페닐)-N-에틸-N-메틸이미도포름아미드, (1.065) N'-(2,5-디메틸-4-{[3-(2,2,3,3-테트라플루오로프로폭시)페닐]술파닐}페닐)-N-에틸-N-메틸이미도포름아미드, (1.066) N'-(2,5-디메틸-4-{[3-(펜타플루오로에톡시)페닐]술파닐}페닐)-N-에틸-N-메틸이미도포름아미드, (1.067) N'-(2,5-디메틸-4-{3-[(1,1,2,2-테트라플루오로에틸)술파닐]페녹시}페닐)-N-에틸-N-메틸이미도포름아미드, (1.068) N'-(2,5-디메틸-4-{3-[(2,2,2-트리플루오로에틸)술파닐]페녹시}페닐)-N-에틸-N-메틸이미도포름아미드, (1.069) N'-(2,5-디메틸-4-{3-[(2,2,3,3-테트라플루오로프로필)술파닐]페녹시}페닐)-N-에틸-N-메틸이미도포름아미드, (1.070) N'-(2,5-디메틸-4-{3-[(펜타플루오로에틸)술파닐]페녹시}페닐)-N-에틸-N-메틸이미도포름아미드, (1.071) N'-(2,5-디메틸-4-페녹시페닐)-N-에틸-N-메틸이미도포름아미드, (1.072) N'-(4-{[3-(디플루오로메톡시)페닐]술파닐}-2,5-디메틸페닐)-N-에틸-N-메틸이미도포름아미드, (1.073) N'-(4-{3-[(디플루오로메틸)술파닐]페녹시}-2,5-디메틸페닐)-N-에틸-N-메틸이미도포름아미드, (1.074) N'-[5-브로모-6-(2,3-디히드로-1H-인덴-2-일옥시)-2-메틸피리딘-3-일]-N-에틸-N-메틸이미도포름아미드, (1.075) N'-{4-[(4,5-디클로로-1,3-티아졸-2-일)옥시]-2,5-디메틸페닐}-N-에틸-N-메틸이미도포름아미드, (1.076) N'-{5-브로모-6-[(1R)-1-(3,5-디플루오로페닐)에톡시]-2-메틸피리딘-3-일}-N-에틸-N-메틸이미도포름아미드, (1.077) N'-{5-브로모-6-[(1S)-1-(3,5-디플루오로페닐)에톡시]-2-메틸피리딘-3-일}-N-에틸-N-메틸이미도포름아미드, (1.078) N'-{5-브로모-6-[(시스-4-이소프로필시클로헥실)옥시]-2-메틸피리딘-3-일}-N-에틸-N-메틸이미도포름아미드, (1.079) N'-{5-브로모-6-[(트랜스-4-이소프로필시클로헥실)옥시]-2-메틸피리딘-3-일}-N-에틸-N-메틸이미도포름아미드, (1.080) N'-{5-브로모-6-[1-(3,5-디플루오로페닐)에톡시]-2-메틸피리딘-3-일}-N-에틸-N-메틸이미도포름아미드, (1.081) 이프펜트리플루코나졸.
2) 복합체 I 또는 II에서의 호흡 사슬 억제제, 예를 들어 (2.001) 벤조빈디플루피르, (2.002) 빅사펜, (2.003) 보스칼리드, (2.004) 카르복신, (2.005) 플루오피람, (2.006) 플루톨라닐, (2.007) 플룩사피록사드, (2.008) 푸라메트피르, (2.009) 이소페타미드, (2.010) 이소피라잠 (안티-에피머 거울상이성질체 1R,4S,9S), (2.011) 이소피라잠 (안티-에피머 거울상이성질체 1S,4R,9R), (2.012) 이소피라잠 (안티-에피머 라세미체 1RS,4SR,9SR), (2.013) 이소피라잠 (신-에피머 라세미체 1RS,4SR,9RS 및 안티-에피머 라세미체 1RS,4SR,9SR의 혼합물), (2.014) 이소피라잠 (신-에피머 거울상이성질체 1R,4S,9R), (2.015) 이소피라잠 (신-에피머 거울상이성질체 1S,4R,9S), (2.016) 이소피라잠 (신-에피머 라세미체 1RS,4SR,9RS), (2.017) 펜플루펜, (2.018) 펜티오피라드, (2.019) 피디플루메토펜, (2.020) 피라지플루미드, (2.021) 세닥산, (2.022) 1,3-디메틸-N-(1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일)-1H-피라졸-4-카르복스아미드, (2.023) 1,3-디메틸-N-[(3R)-1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일]-1H-피라졸-4-카르복스아미드, (2.024) 1,3-디메틸-N-[(3S)-1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일]-1H-피라졸-4-카르복스아미드, (2.025) 1-메틸-3-(트리플루오로메틸)-N-[2'-(트리플루오로메틸)비페닐-2-일]-1H-피라졸-4-카르복스아미드, (2.026) 2-플루오로-6-(트리플루오로메틸)-N-(1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일)벤즈아미드, (2.027) 3-(디플루오로메틸)-1-메틸-N-(1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일)-1H-피라졸-4-카르복스아미드, (2.028) 3-(디플루오로메틸)-1-메틸-N-[(3R)-1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일]-1H-피라졸-4-카르복스아미드, (2.029) 3-(디플루오로메틸)-1-메틸-N-[(3S)-1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일]-1H-피라졸-4-카르복스아미드, (2.030) 플루인다피르, (2.031) 3-(디플루오로메틸)-N-[(3R)-7-플루오로-1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일]-1-메틸-1H-피라졸-4-카르복스아미드, (2.032) 3-(디플루오로메틸)-N-[(3S)-7-플루오로-1,1,3-트리메틸-2,3-디히드로-1H-인덴-4-일]-1-메틸-1H-피라졸-4-카르복스아미드, (2.033) 5,8-디플루오로-N-[2-(2-플루오로-4-{[4-(트리플루오로메틸)피리딘-2-일]옥시}페닐)에틸]퀴나졸린-4-아민, (2.034) N-(2-시클로펜틸-5-플루오로벤질)-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.035) N-(2-tert-부틸-5-메틸벤질)-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.036) N-(2-tert-부틸벤질)-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.037) N-(5-클로로-2-에틸벤질)-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.038) 이소플루시프람, (2.039) N-[(1R,4S)-9-(디클로로메틸렌)-1,2,3,4-테트라히드로-1,4-메타노나프탈렌-5-일]-3-(디플루오로메틸)-1-메틸-1H-피라졸-4-카르복스아미드, (2.040) N-[(1S,4R)-9-(디클로로메틸렌)-1,2,3,4-테트라히드로-1,4-메타노나프탈렌-5-일]-3-(디플루오로메틸)-1-메틸-1H-피라졸-4-카르복스아미드, (2.041) N-[1-(2,4-디클로로페닐)-1-메톡시프로판-2-일]-3-(디플루오로메틸)-1-메틸-1H-피라졸-4-카르복스아미드, (2.042) N-[2-클로로-6-(트리플루오로메틸)벤질]-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.043) N-[3-클로로-2-플루오로-6-(트리플루오로메틸)벤질]-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.044) N-[5-클로로-2-(트리플루오로메틸)벤질]-N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.045) N-시클로프로필-3-(디플루오로메틸)-5-플루오로-1-메틸-N-[5-메틸-2-(트리플루오로메틸)벤질]-1H-피라졸-4-카르복스아미드, (2.046) N-시클로프로필-3-(디플루오로메틸)-5-플루오로-N-(2-플루오로-6-이소프로필벤질)-1-메틸-1H-피라졸-4-카르복스아미드, (2.047) N-시클로프로필-3-(디플루오로메틸)-5-플루오로-N-(2-이소프로필-5-메틸벤질)-1-메틸-1H-피라졸-4-카르복스아미드, (2.048) N-시클로프로필-3-(디플루오로메틸)-5-플루오로-N-(2-이소프로필벤질)-1-메틸-1H-피라졸-4-카르보티오아미드, (2.049) N-시클로프로필-3-(디플루오로메틸)-5-플루오로-N-(2-이소프로필벤질)-1-메틸-1H-피라졸-4-카르복스아미드, (2.050) N-시클로프로필-3-(디플루오로메틸)-5-플루오로-N-(5-플루오로-2-이소프로필벤질)-1-메틸-1H-피라졸-4-카르복스아미드, (2.051) N-시클로프로필-3-(디플루오로메틸)-N-(2-에틸-4,5-디메틸벤질)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.052) N-시클로프로필-3-(디플루오로메틸)-N-(2-에틸-5-플루오로벤질)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.053) N-시클로프로필-3-(디플루오로메틸)-N-(2-에틸-5-메틸벤질)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.054) N-시클로프로필-N-(2-시클로프로필-5-플루오로벤질)-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.055) N-시클로프로필-N-(2-시클로프로필-5-메틸벤질)-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.056) N-시클로프로필-N-(2-시클로프로필벤질)-3-(디플루오로메틸)-5-플루오로-1-메틸-1H-피라졸-4-카르복스아미드, (2.057) 피라프로포인.
3) 복합체 III에서의 호흡 사슬 억제제, 예를 들어 (3.001) 아메톡트라딘, (3.002) 아미술브롬, (3.003) 아족시스트로빈, (3.004) 쿠메톡시스트로빈, (3.005) 쿠목시스트로빈, (3.006) 시아조파미드, (3.007) 디목시스트로빈, (3.008) 에녹사스트로빈, (3.009) 파목사돈, (3.010) 페나미돈, (3.011) 플루페녹시스트로빈, (3.012) 플루옥사스트로빈, (3.013) 크레속심-메틸, (3.014) 메토미노스트로빈, (3.015) 오리사스트로빈, (3.016) 피콕시스트로빈, (3.017) 피라클로스트로빈, (3.018) 피라메토스트로빈, (3.019) 피라옥시스트로빈, (3.020) 트리플록시스트로빈, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-플루오로-2-페닐비닐]옥시}페닐)에틸리덴]아미노}옥시)메틸]페닐}-2-(메톡시이미노)-N-메틸아세트아미드, (3.022) (2E,3Z)-5-{[1-(4-클로로페닐)-1H-피라졸-3-일]옥시}-2-(메톡시이미노)-N,3-디메틸펜트-3-엔아미드, (3.023) (2R)-2-{2-[(2,5-디메틸페녹시)메틸]페닐}-2-메톡시-N-메틸아세트아미드, (3.024) (2S)-2-{2-[(2,5-디메틸페녹시)메틸]페닐}-2-메톡시-N-메틸아세트아미드, (3.025) (3S,6S,7R,8R)-8-벤질-3-[({3-[(이소부티릴옥시)메톡시]-4-메톡시피리딘-2-일}카르보닐)아미노]-6-메틸-4,9-디옥소-1,5-디옥소난-7-일 2-메틸프로파노에이트, (3.026) 만데스트로빈, (3.027) N-(3-에틸-3,5,5-트리메틸시클로헥실)-3-포름아미도-2-히드록시벤즈아미드, (3.028) (2E,3Z)-5-{[1-(4-클로로-2-플루오로페닐)-1H-피라졸-3-일]옥시}-2-(메톡시이미노)-N,3-디메틸펜트-3-엔아미드, (3.029) 메틸 {5-[3-(2,4-디메틸페닐)-1H-피라졸-1-일]-2-메틸벤질}카르바메이트, (3.030) 메틸테트라프롤, (3.031) 플로릴피콕사미드.
4) 유사분열 및 세포 분열 억제제, 예를 들어 (4.001) 카르벤다짐, (4.002) 디에토펜카르브, (4.003) 에타복삼, (4.004) 플루오피콜리드, (4.005) 펜시쿠론, (4.006) 티아벤다졸, (4.007) 티오파네이트-메틸, (4.008) 족사미드, (4.009) 3-클로로-4-(2,6-디플루오로페닐)-6-메틸-5-페닐피리다진, (4.010) 3-클로로-5-(4-클로로페닐)-4-(2,6-디플루오로페닐)-6-메틸피리다진, (4.011) 3-클로로-5-(6-클로로피리딘-3-일)-6-메틸-4-(2,4,6-트리플루오로페닐)피리다진, (4.012) 4-(2-브로모-4-플루오로페닐)-N-(2,6-디플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.013) 4-(2-브로모-4-플루오로페닐)-N-(2-브로모-6-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.014) 4-(2-브로모-4-플루오로페닐)-N-(2-브로모페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.015) 4-(2-브로모-4-플루오로페닐)-N-(2-클로로-6-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.016) 4-(2-브로모-4-플루오로페닐)-N-(2-클로로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.017) 4-(2-브로모-4-플루오로페닐)-N-(2-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.018) 4-(2-클로로-4-플루오로페닐)-N-(2,6-디플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.019) 4-(2-클로로-4-플루오로페닐)-N-(2-클로로-6-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.020) 4-(2-클로로-4-플루오로페닐)-N-(2-클로로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.021) 4-(2-클로로-4-플루오로페닐)-N-(2-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.022) 4-(4-클로로페닐)-5-(2,6-디플루오로페닐)-3,6-디메틸피리다진, (4.023) N-(2-브로모-6-플루오로페닐)-4-(2-클로로-4-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.024) N-(2-브로모페닐)-4-(2-클로로-4-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민, (4.025) N-(4-클로로-2,6-디플루오로페닐)-4-(2-클로로-4-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민.
5) 다중부위 작용을 갖는 화합물, 예를 들어 (5.001) 보르도 혼합물, (5.002) 캅타폴, (5.003) 캅탄, (5.004) 클로로탈로닐, (5.005) 수산화구리, (5.006) 나프텐산구리, (5.007) 산화구리, (5.008) 옥시염화구리, (5.009) 황산구리 (2+), (5.010) 디티아논, (5.011) 도딘, (5.012) 폴페트, (5.013) 만코제브, (5.014) 마네브, (5.015) 메티람, (5.016) 메티람 아연, (5.017) 옥신-구리, (5.018) 프로피네브, (5.019) 황 및 다황화칼슘을 포함하는 황 제제, (5.020) 티람, (5.021) 지네브, (5.022) 지람, (5.023) 6-에틸-5,7-디옥소-6,7-디히드로-5H-피롤로[3',4':5,6][1,4]디티이노[2,3-c][1,2]티아졸-3-카르보니트릴.
6) 숙주 방어를 유도하는 화합물, 예를 들어 (6.001) 아시벤졸라르-S-메틸, (6.002) 이소티아닐, (6.003) 프로베나졸, (6.004) 티아디닐.
7) 아미노산 및/또는 단백질 생합성 억제제, 예를 들어 (7.001) 시프로디닐, (7.002) 카수가마이신, (7.003) 카수가마이신 히드로클로라이드 수화물, (7.004) 옥시테트라시클린, (7.005) 피리메타닐, (7.006) 3-(5-플루오로-3,3,4,4-테트라메틸-3,4-디히드로이소퀴놀린-1-일)퀴놀린.
8) ATP 생산 억제제, 예를 들어 (8.001) 실티오팜.
9) 세포벽 합성 억제제, 예를 들어 (9.001) 벤티아발리카르브, (9.002) 디메토모르프, (9.003) 플루모르프, (9.004) 이프로발리카르브, (9.005) 만디프로파미드, (9.006) 피리모르프, (9.007) 발리페날레이트, (9.008) (2E)-3-(4-tert-부틸페닐)-3-(2-클로로피리딘-4-일)-1-(모르폴린-4-일)프로프-2-엔-1-온, (9.009) (2Z)-3-(4-tert-부틸페닐)-3-(2-클로로피리딘-4-일)-1-(모르폴린-4-일)프로프-2-엔-1-온.
10) 지질 및 막 합성 억제제, 예를 들어 (10.001) 프로파모카르브, (10.002) 프로파모카르브 히드로클로라이드, (10.003) 톨클로포스-메틸.
11) 멜라닌 생합성 억제제, 예를 들어 (11.001) 트리시클라졸, (11.002) 2,2,2-트리플루오로에틸 {3-메틸-1-[(4-메틸벤조일)아미노]부탄-2-일}카르바메이트.
12) 핵산 합성 억제제, 예를 들어 (12.001) 베날락실, (12.002) 베날락실-M (키랄락실), (12.003) 메탈락실, (12.004) 메탈락실-M (메페녹삼).
13) 신호 전달 억제제, 예를 들어 (13.001) 플루디옥소닐, (13.002) 이프로디온, (13.003) 프로시미돈, (13.004) 프로퀴나지드, (13.005) 퀴녹시펜, (13.006) 빈클로졸린.
14) 탈커플링제로서 작용하는 화합물, 예를 들어 (14.001) 플루아지남, (14.002) 멥틸디노캅.
15) 추가의 화합물, 예를 들어 (15.001) 아브시스산, (15.002) 벤티아졸, (15.003) 베톡사진, (15.004) 캅시마이신, (15.005) 카르본, (15.006) 키노메티오나트, (15.007) 쿠프라네브, (15.008) 시플루페나미드, (15.009) 시목사닐, (15.010) 시프로술파미드, (15.011) 플루티아닐, (15.012) 포세틸-알루미늄, (15.013) 포세틸-칼슘, (15.014) 포세틸-소듐, (15.015) 메틸 이소티오시아네이트, (15.016) 메트라페논, (15.017) 밀디오마이신, (15.018) 나타마이신, (15.019) 니켈 디메틸디티오카르바메이트, (15.020) 니트로탈-이소프로필, (15.021) 옥사모카르브, (15.022) 옥사티아피프롤린, (15.023) 옥시펜티인, (15.024) 펜타클로로페놀 및 염, (15.025) 아인산 및 그의 염, (15.026) 프로파모카르브-포세틸레이트, (15.027) 피리오페논 (클라자페논), (15.028) 테부플로퀸, (15.029) 테클로프탈람, (15.030) 톨니파니드, (15.031) 1-(4-{4-[(5R)-5-(2,6-디플루오로페닐)-4,5-디히드로-1,2-옥사졸-3-일]-1,3-티아졸-2-일}피페리딘-1-일)-2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]에타논, (15.032) 1-(4-{4-[(5S)-5-(2,6-디플루오로페닐)-4,5-디히드로-1,2-옥사졸-3-일]-1,3-티아졸-2-일}피페리딘-1-일)-2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]에타논, (15.033) 2-(6-벤질피리딘-2-일)퀴나졸린, (15.034) 디피메티트론, (15.035) 2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]-1-[4-(4-{5-[2-(프로프-2-인-1-일옥시)페닐]-4,5-디히드로-1,2-옥사졸-3-일}-1,3-티아졸-2-일)피페리딘-1-일]에타논, (15.036) 2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]-1-[4-(4-{5-[2-클로로-6-(프로프-2-인-1-일옥시)페닐]-4,5-디히드로-1,2-옥사졸-3-일}-1,3-티아졸-2-일)피페리딘-1-일]에타논, (15.037) 2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]-1-[4-(4-{5-[2-플루오로-6-(프로프-2-인-1-일옥시)페닐]-4,5-디히드로-1,2-옥사졸-3-일}-1,3-티아졸-2-일)피페리딘-1-일]에타논, (15.038) 2-[6-(3-플루오로-4-메톡시페닐)-5-메틸피리딘-2-일]퀴나졸린, (15.039) 2-{(5R)-3-[2-(1-{[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸}피페리딘-4-일)-1,3-티아졸-4-일]-4,5-디히드로-1,2-옥사졸-5-일}-3-클로로페닐 메탄술포네이트, (15.040) 2-{(5S)-3-[2-(1-{[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸}피페리딘-4-일)-1,3-티아졸-4-일]-4,5-디히드로-1,2-옥사졸-5-일}-3-클로로페닐 메탄술포네이트, (15.041) 이프플루페노퀸, (15.042) 2-{2-플루오로-6-[(8-플루오로-2-메틸퀴놀린-3-일)옥시]페닐}프로판-2-올, (15.043) 2-{3-[2-(1-{[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸}피페리딘-4-일)-1,3-티아졸-4-일]-4,5-디히드로-1,2-옥사졸-5-일}-3-클로로페닐 메탄술포네이트, (15.044) 2-{3-[2-(1-{[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸}피페리딘-4-일)-1,3-티아졸-4-일]-4,5-디히드로-1,2-옥사졸-5-일}페닐 메탄술포네이트, (15.045) 2-페닐페놀 및 염, (15.046) 3-(4,4,5-트리플루오로-3,3-디메틸-3,4-디히드로이소퀴놀린-1-일)퀴놀린, (15.047) 퀴노푸멜린, (15.048) 4-아미노-5-플루오로피리미딘-2-올 (호변이성질체 형태: 4-아미노-5-플루오로피리미딘-2(1H)-온), (15.049) 4-옥소-4-[(2-페닐에틸)아미노]부탄산, (15.050) 5-아미노-1,3,4-티아디아졸-2-티올, (15.051) 5-클로로-N'-페닐-N'-(프로프-2-인-1-일)티오펜-2-술포노히드라지드, (15.052) 5-플루오로-2-[(4-플루오로벤질)옥시]피리미딘-4-아민, (15.053) 5-플루오로-2-[(4-메틸벤질)옥시]피리미딘-4-아민, (15.054) 9-플루오로-2,2-디메틸-5-(퀴놀린-3-일)-2,3-디히드로-1,4-벤족사제핀, (15.055) 부트-3-인-1-일 {6-[({[(Z)-(1-메틸-1H-테트라졸-5-일)(페닐)메틸렌]아미노}옥시)메틸]피리딘-2-일}카르바메이트, (15.056) 에틸 (2Z)-3-아미노-2-시아노-3-페닐아크릴레이트, (15.057) 페나진-1-카르복실산, (15.058) 프로필 3,4,5-트리히드록시벤조에이트, (15.059) 퀴놀린-8-올, (15.060) 퀴놀린-8-올 술페이트 (2:1), (15.061) tert-부틸 {6-[({[(1-메틸-1H-테트라졸-5-일)(페닐)메틸렌]아미노}옥시)메틸]피리딘-2-일}카르바메이트, (15.062) 5-플루오로-4-이미노-3-메틸-1-[(4-메틸페닐)술포닐]-3,4-디히드로피리미딘-2(1H)-온, (15.063) 아미노피리펜.
상기 본원에 기재된 바와 같은 부류 (1) 내지 (15)의 모든 명명된 혼합 파트너는 유리 화합물, 및/또는 그의 관능기에 의해 가능하게 되는 경우에, 그의 농업상 허용되는 염의 형태로 존재할 수 있다.
일부 실시양태에서, 화합물 조합물은 하기 성분을 포함한다:
(III.01) + (1.001), (III.01) + (1.002), (III.01) + (1.003), (III.01) + (1.004), (III.01) + (1.005), (III.01) + (1.006), (III.01) + (1.007), (III.01) + (1.008), (III.01) + (1.009), (III.01) + (1.010), (III.01) + (1.011), (III.01) + (1.012), (III.01) + (1.013), (III.01) + (1.014), (III.01) + (1.015), (III.01) + (1.016), (III.01) + (1.017), (III.01) + (1.018), (III.01) + (1.019), (III.01) + (1.020), (III.01) + (1.021), (III.01) + (1.022), (III.01) + (1.023), (III.01) + (1.024), (III.01) + (1.025), (III.01) + (1.026), (III.01) + (1.027), (III.01) + (1.028), (III.01) + (1.029), (III.01) + (1.030), (III.01) + (1.031), (III.01) + (1.032), (III.01) + (1.033), (III.01) + (1.034), (III.01) + (1.035), (III.01) + (1.036), (III.01) + (1.037), (III.01) + (1.038), (III.01) + (1.039), (III.01) + (1.040), (III.01) + (1.041), (III.01) + (1.042), (III.01) + (1.043), (III.01) + (1.044), (III.01) + (1.045), (III.01) + (1.046), (III.01) + (1.047), (III.01) + (1.048), (III.01) + (1.049), (III.01) + (1.050), (III.01) + (1.051), (III.01) + (1.052), (III.01) + (1.053), (III.01) + (1.054), (III.01) + (1.055), (III.01) + (1.056), (III.01) + (1.057), (III.01) + (1.058), (III.01) + (1.059), (III.01) + (1.060), (III.01) + (1.061), (III.01) + (1.062), (III.01) + (1.063), (III.01) + (1.064), (III.01) + (1.065), (III.01) + (1.066), (III.01) + (1.067), (III.01) + (1.068), (III.01) + (1.069), (III.01) + (1.070), (III.01) + (1.071), (III.01) + (1.072), (III.01) + (1.073), (III.01) + (1.074), (III.01) + (1.075), (III.01) + (1.076), (III.01) + (1.077), (III.01) + (1.078), (III.01) + (1.079), (III.01) + (1.080), (III.01) + (1.081), (III.01) + (1.082), (III.01) + (1.083), (III.01) + (1.084), (III.01) + (1.085), (III.01) + (1.086), (III.01) + (2.001), (III.01) + (2.002), (III.01) + (2.003), (III.01) + (2.004), (III.01) + (2.005), (III.01) + (2.006), (III.01) + (2.007), (III.01) + (2.008), (III.01) + (2.009), (III.01) + (2.010), (III.01) + (2.011), (III.01) + (2.012), (III.01) + (2.013), (III.01) + (2.014), (III.01) + (2.015), (III.01) + (2.016), (III.01) + (2.017), (III.01) + (2.018), (III.01) + (2.019), (III.01) + (2.020), (III.01) + (2.021), (III.01) + (2.022), (III.01) + (2.023), (III.01) + (2.024), (III.01) + (2.025), (III.01) + (2.026), (III.01) + (2.027), (III.01) + (2.028), (III.01) + (2.029), (III.01) + (2.030), (III.01) + (2.031), (III.01) + (2.032), (III.01) + (2.033), (III.01) + (2.034), (III.01) + (2.035), (III.01) + (2.036), (III.01) + (2.037), (III.01) + (2.038), (III.01) + (2.039), (III.01) + (2.040), (III.01) + (2.041), (III.01) + (2.042), (III.01) + (2.043), (III.01) + (2.044), (III.01) + (2.045), (III.01) + (2.046), (III.01) + (2.047), (III.01) + (2.048), (III.01) + (2.049), (III.01) + (2.050), (III.01) + (2.051), (III.01) + (2.052), (III.01) + (2.053), (III.01) + (2.054), (III.01) + (2.055), (III.01) + (2.056), (III.01) + (3.001), (III.01) + (3.002), (III.01) + (3.003), (III.01) + (3.004), (III.01) + (3.005), (III.01) + (3.006), (III.01) + (3.007), (III.01) + (3.008), (III.01) + (3.009), (III.01) + (3.010), (III.01) + (3.011), (III.01) + (3.012), (III.01) + (3.013), (III.01) + (3.014), (III.01) + (3.015), (III.01) + (3.016), (III.01) + (3.017), (III.01) + (3.018), (III.01) + (3.019), (III.01) + (3.020), (III.01) + (3.021), (III.01) + (3.022), (III.01) + (3.023), (III.01) + (3.024), (III.01) + (3.025), (III.01) + (3.026), (III.01) + (3.027), (III.01) + (3.028), (III.01) + (3.029), (III.01) + (3.030), (III.01) + (4.001), (III.01) + (4.002), (III.01) + (4.003), (III.01) + (4.004), (III.01) + (4.005), (III.01) + (4.006), (III.01) + (4.007), (III.01) + (4.008), (III.01) + (4.009), (III.01) + (4.010), (III.01) + (4.011), (III.01) + (4.012), (III.01) + (4.013), (III.01) + (4.014), (III.01) + (4.015), (III.01) + (4.016), (III.01) + (4.017), (III.01) + (4.018), (III.01) + (4.019), (III.01) + (4.020), (III.01) + (4.021), (III.01) + (4.022), (III.01) + (4.023), (III.01) + (4.024), (III.01) + (4.025), (III.01) + (5.001), (III.01) + (5.002), (III.01) + (5.003), (III.01) + (5.004), (III.01) + (5.005), (III.01) + (5.006), (III.01) + (5.007), (III.01) + (5.008), (III.01) + (5.009), (III.01) + (5.010), (III.01) + (5.011), (III.01) + (5.012), (III.01) + (5.013), (III.01) + (5.014), (III.01) + (5.015), (III.01) + (5.016), (III.01) + (5.017), (III.01) + (5.018), (III.01) + (5.019), (III.01) + (5.020), (III.01) + (5.021), (III.01) + (5.022), (III.01) + (5.023), (III.01) + (6.001), (III.01) + (6.002), (III.01) + (6.003), (III.01) + (6.004), (III.01) + (7.001), (III.01) + (7.002), (III.01) + (7.003), (III.01) + (7.004), (III.01) + (7.005), (III.01) + (7.006), (III.01) + (8.001), (III.01) + (9.001), (III.01) + (9.002), (III.01) + (9.003), (III.01) + (9.004), (III.01) + (9.005), (III.01) + (9.006), (III.01) + (9.007), (III.01) + (9.008), (III.01) + (9.009), (III.01) + (10.001), (III.01) + (10.002), (III.01) + (10.003), (III.01) + (11.001), (III.01) + (11.002), (III.01) + (12.001), (III.01) + (12.002), (III.01) + (12.003), (III.01) + (12.004), (III.01) + (13.001), (III.01) + (13.002), (III.01) + (13.003), (III.01) + (13.004), (III.01) + (13.005), (III.01) + (13.006), (III.01) + (14.001), (III.01) + (14.002), (III.01) + (15.001), (III.01) + (15.002), (III.01) + (15.003), (III.01) + (15.004), (III.01) + (15.005), (III.01) + (15.006), (III.01) + (15.007), (III.01) + (15.008), (III.01) + (15.009), (III.01) + (15.010), (III.01) + (15.011), (III.01) + (15.012), (III.01) + (15.013), (III.01) + (15.014), (III.01) + (15.015), (III.01) + (15.016), (III.01) + (15.017), (III.01) + (15.018), (III.01) + (15.019), (III.01) + (15.020), (III.01) + (15.021), (III.01) + (15.022), (III.01) + (15.023), (III.01) + (15.024), (III.01) + (15.025), (III.01) + (15.026), (III.01) + (15.027), (III.01) + (15.028), (III.01) + (15.029), (III.01) + (15.030), (III.01) + (15.031), (III.01) + (15.032), (III.01) + (15.033), (III.01) + (15.034), (III.01) + (15.035), (III.01) + (15.036), (III.01) + (15.037), (III.01) + (15.038), (III.01) + (15.039), (III.01) + (15.040), (III.01) + (15.041), (III.01) + (15.042), (III.01) + (15.043), (III.01) + (15.044), (III.01) + (15.045), (III.01) + (15.046), (III.01) + (15.047), (III.01) + (15.048), (III.01) + (15.049), (III.01) + (15.050), (III.01) + (15.051), (III.01) + (15.052), (III.01) + (15.053), (III.01) + (15.054), (III.01) + (15.055), (III.01) + (15.056), (III.01) + (15.057), (III.01) + (15.058), (III.01) + (15.059), (III.01) + (15.060), (III.01) + (15.061), (III.01) + (15.062). (III.01) + (15.063). (III.01) + (15.064). (III.01) + (15.065), (III.01) + 15.066), (III.01) + (15.067), (III.01) + (15.068), (III.01) + (15.069) , (III.01) + (15.070), (III.01) + (15.071), (III.01) + (15.072), (III.01) + (15.073), (III.01) + (15.074), (III.01) + (15.075), (III.01) + (15.076), (III.01), (III.01) + (15.077), (III.01) + (15.078), (III.01) + (15.079), (III.01) + (15. 080), (III.01) + (15.081), (III.01) + (15.082), (III.01) + (15.083), (III.01) + (15.084), (III.01) + (15.085), (III.01) + (15.086), (III.01) + (15.087), (III.01) + (15.088), (III.01) + (15.089), (III.01) + (15.090), (III.01) + (15.091) , (III.01) + (15.092), (III.01) + (15.093), (III.01) + (15.094), (III.01) + (15.095), (III.01) + (15.096), (III.01) + (15.097), (III.01) + (15.098), (III.01) + (15.099), (III.01) + (15.100), (III.01) + (15.101), (III.01) + (15.102), (III.01) + (15.103), (III.01) + (15.104), (III.01) + (15.105), (III.01) + (15.106) , (III.01) + (15.107), (III.01) + (15.108), (III.01) + (15.109), (III.01) + (15.110), (III.01) + (15.111), (III.01) + (15.112). 이들 조합물에서, 제1 성분은 표 III.1에 정의된 바와 같은 화학식 (III)의 화합물 (예를 들어 III.01)이고, 제2 성분은 본원에 정의된 바와 같은 그룹 1 내지 15에서 선택된 살진균제이다. 예를 들어, 조합물 (III.01) + (1.001)은 표 III.1의 화합물 III.01 및 시프로코나졸 (1.001)을 포함하는 조합물에 해당된다.
일부 다른 실시양태에서, 화합물 조합물은 화합물 (III.01)이 표 III.1에서 언급된 화합물 중 임의의 하나로 대체된 상기 기재된 조합물에 해당된다.
이들 조합물에서, 화학식 (III)의 화합물 및 그룹 (1) 내지 (15)으로부터 선택된 살진균제는 100:1 내지 1:100 (화학식 (III)의 화합물 : 그룹 (1) 내지 (15)으로부터 선택된 살진균제)의 범위, 또는 50:1 내지 1:50의 범위, 또는 20:1 내지 1:20의 범위의 중량비로 존재할 수 있다. 중량비 범위의 추가의 예는 95:1 내지 1:95, 90:1 내지 1:90, 85:1 내지 1:85, 80:1 내지 1:80, 75:1 내지 1:75, 70:1 내지 1:70, 65:1 내지 1:65, 60:1 내지 1:60, 55:1 내지 1:55, 45:1 내지 1:45, 40:1 내지 1:40, 35:1 내지 1:35, 30:1 내지 1:30, 25:1 내지 1:25, 15:1 내지 1:15, 10:1 내지 1:10, 5:1 내지 1:5, 4:1 내지 1:4, 3:1 내지 1:3, 2:1 내지 1:2를 포함한다.
본 발명의 화합물(들) 및 조성물은 또한 1종 이상의 생물학적 방제제와 조합될 수 있다.
본 발명의 화합물(들) 및 조성물에 조합될 수 있는 생물학적 방제제의 예는 하기와 같다:
(A) 하기의 군으로부터 선택된 항박테리아제:
(A1) 박테리아, 예컨대 (A1.1) 바실루스 서브틸리스(Bacillus subtilis), 특히 균주 QST713/AQ713 (미국 소재 바이엘 크롭사이언스 엘피(Bayer CropScience LP)로부터 세레나데(SERENADE) OPTI 또는 세레나데 ASO로서 이용 가능함, NRRL 수탁 번호 B21661을 갖고, 미국 특허 번호 6,060,051에 기재되어 있음); (A1.2) 바실루스 아밀로리퀘파시엔스(Bacillus amyloliquefaciens), 특히 균주 D747 (미국 소재 세르티스(Certis)로부터 더블 니켈(Double Nickel)™로서 이용 가능함, 수탁 번호 FERM BP-8234를 갖고, 미국 특허 번호 7,094,592에 개시되어 있음); (A1.3) 바실루스 푸밀루스(Bacillus pumilus), 특히 균주 BU F-33 (NRRL 수탁 번호 50185를 가짐); (A1.4) 바실루스 서브틸리스 변종 아밀로리퀘파시엔스(Bacillus subtilis var. amyloliquefaciens) 균주 FZB24 (미국 소재 노보자임스(Novozymes)로부터 타에그로(Taegro)®로서 이용 가능함); (A1.5) 파에니바실루스(Paenibacillus) 종 균주, 수탁 번호 NRRL B-50972 또는 수탁 번호 NRRL B-67129를 갖고, 국제 특허 공개 번호 WO 2016/154297에 기재되어 있음; 및
(A2) 진균, 예컨대 (A2.1) 아우레오바시디움 풀루란스(Aureobasidium pullulans), 특히 균주 DSM14940의 출아포자; (A2.2) 균주 DSM 14941의 아우레오바시디움 풀루란스 출아포자; (A2.3) 아우레오바시디움 풀루란스, 특히 균주 DSM14940 및 DSM14941의 출아포자의 혼합물;
(B) 하기의 군으로부터 선택된 살진균제:
(B1) 박테리아, 예를 들어 (B1.1) 바실루스 서브틸리스, 특히 균주 QST713/AQ713 (미국 소재 바이엘 크롭사이언스 엘피로부터 세레나데 OPTI 또는 세레나데 ASO로서 이용 가능함, NRRL 수탁 번호 B21661을 갖고, 미국 특허 번호 6,060,051에 기재되어 있음); (B1.2) 바실루스 푸밀루스, 특히 균주 QST2808 (미국 소재 바이엘 크롭사이언스 엘피로부터 소나타(SONATA)®로서 이용 가능함, 수탁 번호 NRRL B-30087을 갖고, 미국 특허 번호 6,245,551에 기재되어 있음); (B1.3) 바실루스 푸밀루스, 특히 균주 GB34 (독일 소재 바이엘 아게(Bayer AG)로부터 일드 쉴드(Yield Shield)®로서 이용 가능함); (B1.4) 바실루스 푸밀루스, 특히 균주 BU F-33 (NRRL 수탁 번호 50185를 가짐); (B1.5) 바실루스 아밀로리퀘파시엔스, 특히 균주 D747 (미국 소재 세르티스로부터 더블 니켈™로서 이용 가능함, 수탁 번호 FERM BP-8234를 갖고, 미국 특허 번호 7,094,592에 개시되어 있음); (B1.6) 바실루스 서브틸리스 Y1336 (대만 소재 비온-테크(Bion-Tech)로부터 바이오박(BIOBAC)® WP로서 이용 가능함, 대만에서 등록 번호 4764, 5454, 5096 및 5277 하에 생물학적 살진균제로서 등록되어 있음); (B1.7) 바실루스 아밀로리퀘파시엔스 균주 MBI 600 (바스프 에스이(BASF SE)로부터 서브틸렉스(SUBTILEX)로서 이용 가능함); (B1.8) 바실루스 서브틸리스 균주 GB03 (독일 소재 바이엘 아게로부터 코디악(Kodiak)®으로서 이용 가능함); (B1.9) 바실루스 서브틸리스 변종 아밀로리퀘파시엔스 균주 FZB24 (버지니아주 살렘 소재 노보자임스 바이올로지칼스 인크.(Novozymes Biologicals Inc.) 또는 노쓰 캐롤라이나주 그린즈버러 소재 신젠타 크롭 프로텍션, 엘엘씨(Syngenta Crop Protection, LLC)로부터 살진균제 타에그로® 또는 타에그로® ECO (EPA 등록 번호 70127-5)로서 이용 가능함; (B1.10) 바실루스 미코이데스(Bacillus mycoides), 분리주 J (미국 소재 세르티스로부터 BmJ TGAI 또는 WG로서 이용 가능함); (B1.11) 바실루스 리케니포르미스(Bacillus licheniformis), 특히 균주 SB3086 (노보자임스로부터 에코가드(EcoGuard)™ 생물살진균제 및 그린 릴리프(Green Releaf)로서 이용 가능함); (B1.12) 파에니바실루스 종 균주, 수탁 번호 NRRL B-50972 또는 수탁 번호 NRRL B-67129를 갖고, 국제 특허 공개 번호 WO 2016/154297에 기재되어 있음.
일부 실시양태에서, 생물학적 방제제는 펜기신 또는 플리파스타틴-유형 화합물, 이투린-유형 화합물 및/또는 서팩틴-유형 화합물을 생산하는 바실루스 서브틸리스 또는 바실루스 아밀로리퀘파시엔스 균주이다. 배경기술을 위해, 하기 종설 논문을 참조한다: Ongena, M., et al., "Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol," Trends in Microbiology, Vol 16, No. 3, March 2008, pp. 115-125. 리포펩티드를 생산할 수 있는 바실루스 균주는 바실루스 서브틸리스 QST713 (미국 소재 바이엘 크롭사이언스 엘피로부터 세레나데 OPTI 또는 세레나데 ASO로서 이용 가능함, NRRL 수탁 번호 B21661를 갖고, 미국 특허 번호 6,060,051에 기재되어 있음), 바실루스 아밀로리퀘파시엔스 균주 D747 (미국 소재 세르티스로부터 더블 니켈™로서 이용 가능함, 수탁 번호 FERM BP-8234를 갖고, 미국 특허 번호 7,094,592에 개시되어 있음); 바실루스 서브틸리스 MBI600 (미국 소재 베커 언더우드로부터 서브틸렉스®로서 이용 가능함, EPA 등록 번호 71840-8); 바실루스 서브틸리스 Y1336 (대만 소재 비온-테크로부터 바이오박® WP로서 이용 가능함, 대만에서 등록 번호 4764, 5454, 5096 및 5277 하에 생물학적 살진균제로 등록되어 있음); 바실루스 아밀로리퀘파시엔스, 특히 균주 FZB42 (독일 소재 아비텝(ABiTEP)으로부터 리조비탈(RHIZOVITAL)®로서 이용 가능함); 및 바실루스 서브틸리스 변종 아밀로리퀘파시엔스 FZB24 (버지니아주 살렘 소재 노보자임스 바이올로지칼스 인크. 또는 노쓰 캐롤라이나주 그린즈버러 소재 신젠타 크롭 프로텍션, 엘엘씨로부터 살진균제 타에그로® 또는 타에그로® ECO (EPA 등록 번호 70127-5)로서 이용 가능함)을 포함한다.
(B2) 진균, 예를 들어: (B2.1) 코니오티리움 미니탄스(Coniothyrium minitans), 특히 균주 CON/M/91-8 (수탁 번호 DSM-9660; 예를 들어 바이엘로부터의 콘스탄스(Contans)®); (B2.2) 메치니코위아 프룩티콜라(Metschnikowia fructicola), 특히 균주 NRRL Y-30752 (예를 들어 쉐머(Shemer)®); (B2.3) 미크로스파에롭시스 오크라세아(Microsphaeropsis ochracea) (예를 들어 프로피타(Prophyta)로부터의 마이크록스(Microx)®); (B2.5) 트리코더마(Trichoderma) 종, 예컨대 트리코더마 아트로비리데(Trichoderma atroviride), 균주 SC1 (국제 출원 번호 PCT/IT2008/000196에 기재되어 있음); (B2.6) 트리코더마 하르지아눔 리파이(Trichoderma harzianum rifai) 균주 KRL-AG2 (균주 T-22, /ATCC 208479로도 공지됨, 예를 들어 미국 소재 바이오웍스(BioWorks)로부터의 플랜트쉴드(PLANTSHIELD) T-22G, 루트쉴드(Rootshield)® 및 터프쉴드(TurfShield)); (B2.14) 글리오클라디움 로세움(Gliocladium roseum), 더블유.에프. 스톤맨 캄파니 엘엘씨(W.F. Stoneman Company LLC)로부터의 균주 321U; (B2.35) 탈라로미세스 플라부스(Talaromyces flavus), 균주 V117b; (B2.36) 트리코더마 아스페렐룸(Trichoderma asperellum), 이사그로(Isagro)로부터의 균주 ICC 012; (B2.37) 트리코더마 아스페렐룸, 균주 SKT-1 (예를 들어 쿠미아이 케미칼 인더스트리(Kumiai Chemical Industry)로부터의 ECO-호프(ECO-HOPE)®); (B2.38) 트리코더마 아트로비리데, 균주 CNCM I-1237 (예를 들어 프랑스 소재 아그록신(Agrauxine)으로부터의 에스키브(Esquive)® WP); (B2.39) 트리코더마 아트로비리데, 균주 번호 V08/002387; (B2.40) 트리코더마 아트로비리데, 균주 NMI 번호 V08/002388; (B2.41) 트리코더마 아트로비리데, 균주 NMI 번호 V08/002389; (B2.42) 트리코더마 아트로비리데, 균주 NMI 번호 V08/002390; (B2.43) 트리코더마 아트로비리데, 균주 LC52 (예를 들어 아그림 테크놀로지스 리미티드(Agrimm Technologies Limited)에 의한 테넷(Tenet)); (B2.44) 트리코더마 아트로비리데, 균주 ATCC 20476 (IMI 206040); (B2.45) 트리코더마 아트로비리데, 균주 T11 (IMI352941/ CECT20498); (B2.46) 트리코더마 하르마툼(Trichoderma harmatum); (B2.47) 트리코더마 하르지아눔; (B2.48) 트리코더마 하르지아눔 리파이 T39 (예를 들어 미국 소재 마크테심(Makhteshim)으로부터의 트리코덱스(Trichodex)®); (B2.49) 트리코더마 하르지아눔, 특히, 균주 KD (예를 들어 바이올로지컬 컨트롤 프로덕츠, 에스에이(Biological Control Products, SA) (베커 언더우드에 의해 입수됨)로부터의 트리코플러스(Trichoplus)); (B2.50) 트리코더마 하르지아눔, 균주 ITEM 908 (예를 들어 코퍼트(Koppert)로부터의 트리아눔(Trianum)-P); (B2.51) 트리코더마 하르지아눔, 균주 TH35 (예를 들어 마이컨트롤(Mycontrol)에 의한 루트-프로(Root-Pro)); (B2.52) 트리코더마 비렌스(Trichoderma virens) (글리오클라디움 비렌스(Gliocladium virens)로도 공지됨), 특히 균주 GL-21 (예를 들어 미국 소재 세르티스에 의한 소일가드(SoilGard) 12G); (B2.53) 트리코더마 비리데(Trichoderma viride), 균주 TV1 (예를 들어 코퍼트에 의한 트리아눔-P); (B2.54) 암펠로미세스 퀴스쿠알리스(Ampelomyces quisqualis), 특히 균주 AQ 10 (예를 들어 인트라켐바이오 이탈리아(IntrachemBio Italia)에 의한 AQ 10®); (B2.56) 아우레오바시디움 풀루란스(Aureobasidium pullulans), 특히 균주 DSM14940의 출아포자; (B2.57) 아우레오바시디움 풀루란스, 특히 균주 DSM 14941의 출아포자; (B2.58) 아우레오바시디움 풀루란스, 특히 균주 DSM14940 및 DSM 14941의 출아포자의 혼합물 (예를 들어 스위스 소재 바이오-펌(bio-ferm)에 의한 보텍토르(Botector)®); (B2.64) 클라도스포리움 클라도스포리오이데스(Cladosporium cladosporioides), 균주 H39 (슈티히팅 딘스트 란트보우브쿤디히 온데르최크 (Stichting Dienst Landbouwkundig Onderzoek)에 의함); (B2.69) 글리오클라디움 카테눌라툼 (동의어: 클로노스타키스 로세아 에프. 카테눌라타(Clonostachys rosea f. catenulata)) 균주 J1446 (예를 들어 에이쥐바이오 인크.(AgBio Inc.)에 의한 프리스톱(Prestop)® 및 또한 예를 들어 케미라 아그로 오와이(Kemira Agro Oy)에 의한 프리마스톱(Primastop)®); (B2.70) 균주 KV01의 레카니실리움 레카니이(Lecanicillium lecanii) (이전에 베르티실리움 레카니이(Verticillium lecanii)로 공지됨) 분생포자 (예를 들어 코퍼트/아리스타(Koppert/Arysta)에 의한 베르타렉(Vertalec)®); (B2.71) 페니실리움 베르미쿨라툼(Penicillium vermiculatum); (B2.72) 피키아 아노말라(Pichia anomala), 균주 WRL-076 (NRRL Y-30842); (B2.75) 트리코더마 아트로비리데, 균주 SKT-1 (FERM P-16510); (B2.76) 트리코더마 아트로비리데, 균주 SKT-2 (FERM P-16511); (B2.77) 트리코더마 아트로비리데, 균주 SKT-3 (FERM P-17021); (B2.78) 트리코더마 감시이(Trichoderma gamsii) (이전에 티. 비리데(T. viride)), 균주 ICC080 (IMI CC 392151 CABI, 예를 들어 아그로비오솔 데 멕시코 에세.아. 데 쎄.우베.(AGROBIOSOL DE MEXICO, S.A. DE C.V.)에 의한 바이오더마(BioDerma)); (B2.79) 트리코더마 하르지아눔, 균주 DB 103 (예를 들어, 다구타트 바이오랩(Dagutat Biolab)에 의한 T-Gro 7456); (B2.80) 트리코더마 폴리스포룸, 균주 IMI 206039 (예를 들어 스웨덴 소재 비납 바이오-이노베이션 에이비(BINAB Bio-Innovation AB)에 의한 비납 TF WP); (B2.81) 트리코더마 스트로마티쿰(Trichoderma stromaticum) (예를 들어 브라질 소재 세플락(Ceplac)에 의한 트리코밥(Tricovab)); (B2.83) 울로클라디움 오우데만시이(Ulocladium oudemansii), 특히 균주 HRU3 (예를 들어 뉴질랜드 소재 보트리-젠 리미티드(Botry-Zen Ltd)에 의한 보트리-젠(Botry-Zen)®); (B2.84) 베르티실리움 알보-아트룸(Verticillium albo-atrum) (이전에 브이. 달리아에(V. dahliae)), 균주 WCS850 (CBS 276.92; 예를 들어 트리 케어 이노베이션스(Tree Care Innovations)에 의한 더치 트리그(Dutch Trig)); (B2.86) 베르티실리움 클라미도스포리움(Verticillium chlamydosporium); (B2.87) 트리코더마 아스페렐룸 균주 ICC 012 및 트리코더마 감시이 균주 ICC 080의 혼합물 (예를 들어 미국 소재 바이엘 크롭사이언스 엘피로부터 바이오-탐(BIO-TAM)™으로 공지된 생성물).
본 발명의 화합물(들) 및 조성물과 조합될 수 있는 생물학적 방제제의 추가의 예는 하기와 같다:
바실루스 세레우스(Bacillus cereus), 특히 비. 세레우스 균주 CNCM I-1562 및 바실루스 피르무스(Bacillus firmus), 균주 I-1582 (수탁 번호 CNCM I-1582), 바실루스 서브틸리스 균주 OST 30002 (수탁 번호 NRRL B-50421), 바실루스 투린기엔시스(Bacillus thuringiensis), 특히 비. 투린기엔시스 아종 이스라엘렌시스(israelensis) (혈청형 H-14), 균주 AM65-52 (수탁 번호 ATCC 1276), 비. 투린기엔시스 아종 아이자와이(aizawai), 특히 균주 ABTS-1857 (SD-1372), 비. 투린기엔시스 아종 쿠르스타키(kurstaki) 균주 HD-1, 비. 투린기엔시스 아종 테네브리오니스(tenebrionis) 균주 NB 176 (SD-5428), 파스테우리아 페네트란스(Pasteuria penetrans), 파스테우리아(Pasteuria) 종 (로틸렌쿨루스 레니포르미스 선충류)-PR3 (수탁 번호 ATCC SD-5834), 스트렙토미세스 미크로플라부스(Streptomyces microflavus) 균주 AQ6121 (= QRD 31.013, NRRL B-50550), 및 스트렙토미세스 갈부스(Streptomyces galbus) 균주 AQ 6047 (수탁 번호 NRRL 30232)로 이루어진 군으로부터 선택된 박테리아;
뷰베리아 바시아나(Beauveria bassiana), 특히 균주 ATCC 74040, 레카니실리움 종, 특히 균주 HRO LEC 12, 메타리지움 아니소플리아에(Metarhizium anisopliae), 특히 균주 F52 (DSM3884 또는 ATCC 90448), 파에실로미세스 푸모소로세우스(Paecilomyces fumosoroseus) (현재: 이사리아 푸모소로세아(Isaria fumosorosea)), 특히 균주 IFPC 200613, 또는 균주 아폽카(Apopka) 97 (수탁 번호 ATCC 20874), 및 파에실로미세스 릴라시누스(Paecilomyces lilacinus), 특히 피. 릴라시누스 균주 251 (AGAL 89/030550)로 이루어진 군으로부터 선택된 진균 및 효모;
아독소피에스 오라나(Adoxophyes orana) (여름 과일 토르트릭스) 과립병 바이러스 (GV), 시디아 포모넬라(Cydia pomonella) (코들링 나방) 과립병 바이러스 (GV), 헬리코베르파 아르미게라(Helicoverpa armigera) (목화다래벌레) 핵 다각체병 바이러스 (NPV), 스포도프테라 엑시구아(Spodoptera exigua) (비트 거염벌레) mNPV, 스포도프테라 프루기페르다(Spodoptera frugiperda) (가을 거염벌레) mNPV, 및 스포도프테라 리토랄리스(Spodoptera littoralis) (아프리카 목화 잎벌레) NPV로 이루어진 군으로부터 선택된 바이러스.
식물 또는 식물 부분 또는 식물 기관에 '접종물'로서 첨가될 수 있으며 그의 특정한 특성에 의해 식물 성장 및 식물 건강을 촉진하는 박테리아 및 진균. 예는 하기와 같다: 아그로박테리움(Agrobacterium) 종, 아조리조비움 카울리노단스(Azorhizobium caulinodans), 아조스피릴룸(Azospirillum) 종, 아조토박터(Azotobacter) 종, 브라디리조비움(Bradyrhizobium) 종, 부르크홀데리아(Burkholderia) 종, 특히 부르크홀데리아 세파시아 (이전에 슈도모나스 세파시아(Pseudomonas cepacia)로 공지됨), 기가스포라(Gigaspora) 종, 또는 기가스포라 모노스포룸(Gigaspora monosporum), 글로무스(Glomus) 종, 라카리아(Laccaria) 종, 락토바실루스 부크네리(Lactobacillus buchneri), 파라글로무스(Paraglomus) 종, 피솔리투스 틴크토루스(Pisolithus tinctorus), 슈도모나스(Pseudomonas) 종, 리조비움(Rhizobium) 종, 특히 리조비움 트리폴리이(Rhizobium trifolii), 리조포곤(Rhizopogon) 종, 스클레로더마(Scleroderma) 종, 수일루스(Suillus) 종, 및 스트렙토미세스(Streptomyces) 종.
생물학적 방제제로서 사용될 수 있는 식물 추출물, 및 단백질 및 2차 대사물을 포함하는 미생물에 의해 형성된 생성물, 예컨대 알리움 사티붐(Allium sativum), 아르테미시아 아브신티움(Artemisia absinthium), 아자디라크틴, 바이오키퍼(Biokeeper) WP, 카시아 니그리칸스(Cassia nigricans), 셀라스트루스 안굴라투스(Celastrus angulatus), 케노포디움 안텔민티쿰(Chenopodium anthelminticum), 키틴, 아모르-젠(Armour-Zen), 드리오프테리스 필릭스-마스(Dryopteris filix-mas), 에퀴세툼 아르벤세(Equisetum arvense), 포툰 아자, 푼가스톱, 헤즈 업 (케노포디움 퀴노아(Chenopodium quinoa) 사포닌 추출물), 피레트룸/피레트린(Pyrethrum/Pyrethrins), 콰시아 아마라(Quassia amara), 퀘르쿠스(Quercus), 퀼라야(Quillaja), 레갈리아(Regalia), "레퀴엠(Requiem)™ 살곤충제", 로테논, 리아니아/리아노딘(ryania/ryanodine), 심피툼 오피시날레(Symphytum officinale), 타나세툼 불가레(Tanacetum vulgare), 티몰, 트리액트(Triact) 70, 트리콘(TriCon), 트로파에올룸 마주스(Tropaeulum majus), 우르티카 디오이카(Urtica dioica), 베라트리딘, 비스쿰 알붐(Viscum album), 브라시카세아에(Brassicaceae) 추출물, 특히 유지종자 평지 분말 또는 겨자 분말.
본 발명의 화합물(들) 및 조성물과 혼합될 수 있는 살곤충제, 살진드기제 및 살선충제 각각의 예는 하기와 같다:
(1) 아세틸콜린에스테라제 (AChE) 억제제, 예컨대, 예를 들어, 카르바메이트, 예를 들어 알라니카르브, 알디카르브, 벤디오카르브, 벤푸라카르브, 부토카르복심, 부톡시카르복심, 카르바릴, 카르보푸란, 카르보술판, 에티오펜카르브, 페노부카르브, 포르메타네이트, 푸라티오카르브, 이소프로카르브, 메티오카르브, 메토밀, 메톨카르브, 옥사밀, 피리미카르브, 프로폭수르, 티오디카르브, 티오파녹스, 트리아자메이트, 트리메타카르브, XMC 및 크실릴카르브; 또는 유기포스페이트, 예를 들어 아세페이트, 아자메티포스, 아진포스-에틸, 아진포스-메틸, 카두사포스, 클로르에톡시포스, 클로르펜빈포스, 클로르메포스, 클로르피리포스-메틸, 쿠마포스, 시아노포스, 디메톤-S-메틸, 디아지논, 디클로르보스/DDVP, 디크로토포스, 디메토에이트, 디메틸빈포스, 디술포톤, EPN, 에티온, 에토프로포스, 팜푸르, 페나미포스, 페니트로티온, 펜티온, 포스티아제이트, 헵테노포스, 이미시아포스, 이소펜포스, 이소프로필 O-(메톡시아미노티오포스포릴) 살리실레이트, 이속사티온, 말라티온, 메카르밤, 메타미도포스, 메티다티온, 메빈포스, 모노크로토포스, 날레드, 오메토에이트, 옥시데메톤-메틸, 파라티온-메틸, 펜토에이트, 포레이트, 포살론, 포스메트, 포스파미돈, 폭심, 피리미포스-메틸, 프로페노포스, 프로페탐포스, 프로티오포스, 피라클로포스, 피리다펜티온, 퀴날포스, 술포텝, 테부피림포스, 테메포스, 테르부포스, 테트라클로르빈포스, 티오메톤, 트리아조포스, 트리클로르폰 및 바미도티온.
(2) GABA-게이팅 클로라이드 채널 차단제, 예컨대, 예를 들어, 시클로디엔-유기염소, 예를 들어 클로르단 및 엔도술판 또는 페닐피라졸 (피프롤), 예를 들어 에티프롤 및 피프로닐.
(3) 나트륨 채널 조정제, 예컨대, 예를 들어, 피레트로이드, 예를 들어 아크리나트린, 알레트린, d-시스-트랜스 알레트린, d-트랜스 알레트린, 비펜트린, 비오알레트린, 비오알레트린 s-시클로펜테닐 이성질체, 비오레스메트린, 시클로프로트린, 시플루트린, 베타-시플루트린, 시할로트린, 람다-시할로트린, 감마-시할로트린, 시페르메트린, 알파-시페르메트린, 베타-시페르메트린, 세타-시페르메트린, 제타-시퍼메트린, 시페노트린 [(1R)-트랜스-이성질체], 델타메트린, 엠펜트린 [(EZ)-(1R)-이성질체], 에스펜발레레이트, 에토펜프록스, 펜프로파트린, 펜발레레이트, 플루시트리네이트, 플루메트린, 타우-플루발리네이트, 할펜프록스, 이미프로트린, 카데트린, 몸플루오로트린, 페르메트린, 페노트린 [(1R)-트랜스-이성질체], 프랄레트린, 피레트린 (피레트룸), 레스메트린, 실라플루오펜, 테플루트린, 테트라메트린, 테트라메트린 [(1R)-이성질체)], 트랄로메트린 및 트랜스플루트린 또는 DDT 또는 메톡시클로르.
(4) 니코틴성 아세틸콜린 수용체 (nAChR) 경쟁적 조정제, 예컨대, 예를 들어, 네오니코티노이드, 예를 들어 아세타미프리드, 클로티아니딘, 디노테푸란, 이미다클로프리드, 니텐피람, 티아클로프리드 및 티아메톡삼 또는 니코틴 또는 술폭사플로르 또는 플루피라디푸론.
(5) 니코틴성 아세틸콜린 수용체 (nAChR) 알로스테릭 조정제, 예컨대, 예를 들어, 스피노신, 예를 들어 스피네토람 및 스피노사드.
(6) 글루타메이트-게이팅 클로라이드 채널 (GluCl) 알로스테릭 조정제, 예컨대, 예를 들어, 아베르멕틴/밀베마이신, 예를 들어 아바멕틴, 에마멕틴 벤조에이트, 레피멕틴 및 밀베멕틴.
(7) 유충 호르몬 모방체, 예컨대, 예를 들어, 유충 호르몬 유사체, 예를 들어 히드로프렌, 키노프렌 및 메토프렌 또는 페녹시카르브 또는 피리프록시펜.
(8) 기타 비-특이적 (다중-부위) 억제제, 예컨대, 예를 들어, 알킬 할라이드, 예를 들어 메틸 브로마이드 및 다른 알킬 할라이드; 또는 클로로피크린 또는 술푸릴 플루오라이드 또는 보락스 또는 토주석 또는 메틸 이소시아네이트 발생기, 예를 들어 디아조메트 및 메탐.
(9) 현음 기관 조정제, 예컨대, 예를 들어 피메트로진 또는 플로니카미드.
(10) 응애 성장 억제제, 예컨대, 예를 들어 클로펜테진, 헥시티아족스 및 디플로비다진 또는 에톡사졸.
(11) 곤충 장 막 미생물 파괴제, 예컨대, 예를 들어 바실루스 투린기엔시스 아종 이스라엘렌시스, 바실루스 스파에리쿠스(Bacillus sphaericus), 바실루스 투린기엔시스 아종 아이자와이, 바실루스 투린기엔시스 아종 쿠르스타키, 바실루스 투린기엔시스 아종 테네브리오니스, 및 B.t. 식물 단백질: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1.
(12) 미토콘드리아 ATP 신타제 억제제, 예컨대 ATP 교란제, 예컨대, 예를 들어 디아펜티우론 또는 유기주석 화합물, 예를 들어 아조시클로틴, 시헥사틴 및 펜부타틴 옥시드 또는 프로파르기트 또는 테트라디폰.
(13) 양성자 구배의 붕괴를 통한 산화성 인산화의 탈커플링제, 예컨대, 예를 들어 클로르페나피르, DNOC 및 술플루라미드.
(14) 니코틴성 아세틸콜린 수용체 채널 차단제, 예컨대, 예를 들어 벤술탑, 카르탑 히드로클로라이드, 티오시클람 및 티오술탑-소듐.
(15) 제0형 키틴 생합성 억제제, 예컨대, 예를 들어 비스트리플루론, 클로르플루아주론, 디플루벤주론, 플루시클록수론, 플루페녹수론, 헥사플루무론, 루페누론, 노발루론, 노비플루무론, 테플루벤주론 및 트리플루무론.
(16) 제1형 키틴 생합성 억제제, 예를 들어 부프로페진.
(17) 탈피 교란제 (특히 파리목, 즉, 쌍시류에 대한 것), 예컨대, 예를 들어, 시로마진.
(18) 엑디손 수용체 효능제, 예컨대, 예를 들어 크로마페노지드, 할로페노지드, 메톡시페노지드 및 테부페노지드.
(19) 옥토파민 수용체 효능제, 예컨대, 예를 들어, 아미트라즈.
(20) 미토콘드리아 복합체 III 전자 수송 억제제, 예컨대, 예를 들어, 히드라메틸논 또는 아세퀴노실 또는 플루아크리피림.
(21) 미토콘드리아 복합체 I 전자 수송 억제제, 예컨대, 예를 들어 METI 살진드기제의 군으로부터의 것, 예를 들어 페나자퀸, 펜피록시메이트, 피리미디펜, 피리다벤, 테부펜피라드 및 톨펜피라드 또는 로테논 (데리스(Derris)).
(22) 전압-의존성 나트륨 채널 차단제, 예컨대, 예를 들어 인독사카르브 또는 메타플루미존.
(23) 아세틸 CoA 카르복실라제 억제제, 예컨대, 예를 들어 테트론산 및 테트람산 유도체, 예를 들어 스피로디클로펜, 스피로메시펜 및 스피로테트라마트.
(24) 미토콘드리아 복합체 IV 전자 수송 억제제, 예컨대, 예를 들어 포스핀, 예를 들어 인화알루미늄, 인화칼슘, 포스핀 및 인화아연 또는 시아나이드, 시안화칼슘, 시안화칼륨 및 시안화나트륨.
(25) 미토콘드리아 복합체 II 전자 수송 억제제, 예컨대, 예를 들어 베타-케토 니트릴 유도체, 예를 들어 시에노피라펜 및 시플루메토펜 및 카르복스아닐리드, 예컨대 예를 들어 피플루부미드.
(28) 리아노딘 수용체 조정제, 예컨대, 예를 들어 디아미드, 예를 들어 클로란트라닐리프롤, 시안트라닐리프롤 및 플루벤디아미드,
추가의 활성 화합물, 예컨대, 예를 들어 아피도피로펜, 아폭솔라너, 아자디라크틴, 벤클로티아즈, 벤족시메이트, 비페나제이트, 브로플라닐리드, 브로모프로필레이트, 키노메티오나트, 클로로프랄레트린, 크리올라이트, 시클라닐리프롤, 시클록사프리드, 시할로디아미드, 디클로로메조티아즈, 디코폴, 엡실론-메토플루트린, 엡실론-몸플루오로트린, 플로메토퀸, 플루아자인돌리진, 플루엔술폰, 플루페네림, 플루페녹시스트로빈, 플루피프롤, 플루헥사폰, 플루오피람, 플루랄라너, 플룩사메타미드, 푸페노지드, 구아디피르, 헵타플루트린, 이미다클로티즈, 이프로디온, 카파-비펜트린, 카파-테플루트린, 로틸라너, 메페르플루트린, 파이총딩, 피리달릴, 피리플루퀴나존, 피리미노스트로빈, 스피로부디클로펜, 테트라메틸플루트린, 테트라닐리프롤, 테트라클로란트라닐리프롤, 티골라너, 티옥사자펜, 티오플루옥시메이트, 트리플루메조피림 및 아이오도메탄; 추가적으로 바실루스 피르무스를 기재로 하는 제제 (I-1582, 바이오님(BioNeem), 보티보(Votivo)), 및 하기 화합물: 1-{2-플루오로-4-메틸-5-[(2,2,2-트리플루오로에틸)술피닐]페닐}-3-(트리플루오로메틸)-1H-1,2,4-트리아졸-5-아민 (WO2006/043635로부터 공지됨) (CAS 885026-50-6), {1'-[(2E)-3-(4-클로로페닐)프로프-2-엔-1-일]-5-플루오로스피로[인돌-3,4'-피페리딘]-1(2H)-일}(2-클로로피리딘-4-일)메타논 (WO2003/106457로부터 공지됨) (CAS 637360-23-7), 2-클로로-N-[2-{1-[(2E)-3-(4-클로로페닐)프로프-2-엔-1-일]피페리딘-4-일}-4-(트리플루오로메틸)페닐]이소니코틴아미드 (WO2006/003494로부터 공지됨) (CAS 872999-66-1), 3-(4-클로로-2,6-디메틸페닐)-4-히드록시-8-메톡시-1,8-디아자스피로[4.5]데스-3-엔-2-온 (WO 2010052161로부터 공지됨) (CAS 1225292-17-0), 3-(4-클로로-2,6-디메틸페닐)-8-메톡시-2-옥소-1,8-디아자스피로[4.5]데스-3-엔-4-일 에틸 카르보네이트 (EP2647626으로부터 공지됨) (CAS 1440516-42-6), 4-(부트-2-인-1-일옥시)-6-(3,5-디메틸피페리딘-1-일)-5-플루오로피리미딘 (WO2004/099160로부터 공지됨) (CAS 792914-58-0), PF1364 (JP2010/018586으로부터 공지됨) (CAS 1204776-60-2), N-[(2E)-1-[(6-클로로피리딘-3-일)메틸]피리딘-2(1H)-일리덴]-2,2,2-트리플루오로아세트아미드 (WO2012/029672로부터 공지됨) (CAS 1363400-41-2), (3E)-3-[1-[(6-클로로-3-피리딜)메틸]-2-피리딜리덴]-1,1,1-트리플루오로-프로판-2-온 (WO2013/144213로부터 공지됨) (CAS 1461743-15-6), , N-[3-(벤질카르바모일)-4-클로로페닐]-1-메틸-3-(펜타플루오로에틸)-4-(트리플루오로메틸)-1H-피라졸-5-카르복스아미드 (WO2010/051926으로부터 공지됨) (CAS 1226889-14-0), 5-브로모-4-클로로-N-[4-클로로-2-메틸-6-(메틸카르바모일)페닐]-2-(3-클로로-2-피리딜)피라졸-3-카르복스아미드 (CN103232431로부터 공지됨) (CAS 1449220-44-3), 4-[5-(3,5-디클로로페닐)-4,5-디히드로-5-(트리플루오로메틸)-3-이속사졸릴]-2-메틸-N-(시스-1-옥시도-3-티에타닐)-벤즈아미드, 4-[5-(3,5-디클로로페닐)-4,5-디히드로-5-(트리플루오로메틸)-3-이속사졸릴]-2-메틸-N-(트랜스-1-옥시도-3-티에타닐)-벤즈아미드 및 4-[(5S)-5-(3,5-디클로로페닐)-4,5-디히드로-5-(트리플루오로메틸)-3-이속사졸릴]-2-메틸-N-(시스-1-옥시도-3-티에타닐)벤즈아미드 (WO 2013/050317 A1로부터 공지됨) (CAS 1332628-83-7), N-[3-클로로-1-(3-피리디닐)-1H-피라졸-4-일]-N-에틸-3-[(3,3,3-트리플루오로프로필)술피닐]-프로판아미드, (+)-N-[3-클로로-1-(3-피리디닐)-1H-피라졸-4-일]-N-에틸-3-[(3,3,3-트리플루오로프로필)술피닐]-프로판아미드 및 (-)-N-[3-클로로-1-(3-피리디닐)-1H-피라졸-4-일]-N-에틸-3-[(3,3,3-트리플루오로프로필)술피닐]-프로판아미드 (WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1로부터 공지됨) (CAS 1477923-37-7), 5-[[(2E)-3-클로로-2-프로펜-1-일]아미노]-1-[2,6-디클로로-4-(트리플루오로메틸)페닐]-4-[(트리플루오로메틸)술피닐]-1H-피라졸-3-카르보니트릴 (CN 101337937 A로부터 공지됨) (CAS 1105672-77-2), 3-브로모-N-[4-클로로-2-메틸-6-[(메틸아미노)티옥소메틸]페닐]-1-(3-클로로-2-피리디닐)-1H-피라졸-5-카르복스아미드, (류다이번자쉬안난(Liudaibenjiaxuanan), CN 103109816 A로부터 공지됨) (CAS 1232543-85-9); N-[4-클로로-2-[[(1,1-디메틸에틸)아미노]카르보닐]-6-메틸페닐]-1-(3-클로로-2-피리디닐)-3-(플루오로메톡시)-1H-피라졸-5-카르복스아미드 (WO 2012/034403 A1로부터 공지됨) (CAS 1268277-22-0), N-[2-(5-아미노-1,3,4-티아디아졸-2-일)-4-클로로-6-메틸페닐]-3-브로모-1-(3-클로로-2-피리디닐)-1H-피라졸-5-카르복스아미드 (WO 2011/085575 A1로부터 공지됨) (CAS 1233882-22-8), 4-[3-[2,6-디클로로-4-[(3,3-디클로로-2-프로펜-1-일)옥시]페녹시]프로폭시]-2-메톡시-6-(트리플루오로메틸)-피리미딘 (CN 101337940 A로부터 공지됨) (CAS 1108184-52-6); (2E)- 및 2(Z)-2-[2-(4-시아노페닐)-1-[3-(트리플루오로메틸)페닐]에틸리덴]-N-[4-(디플루오로메톡시)페닐]-히드라진카르복스아미드 (CN 101715774 A로부터 공지됨) (CAS 1232543-85-9); 3-(2,2-디클로로에테닐)-2,2-디메틸-4-(1H-벤즈이미다졸-2-일)페닐-시클로프로판카르복실산 에스테르 (CN 103524422 A로부터 공지됨) (CAS 1542271-46-4); (4aS)-7-클로로-2,5-디히드로-2-[[(메톡시카르보닐)[4-[(트리플루오로메틸)티오]페닐]아미노]카르보닐]-인데노[1,2-e][1,3,4]옥사디아진-4a(3H)-카르복실산 메틸 에스테르 (CN 102391261 A로부터 공지됨) (CAS 1370358-69-2); 6-데옥시-3-O-에틸-2,4-디-O-메틸-, 1-[N-[4-[1-[4-(1,1,2,2,2-펜타플루오로에톡시)페닐]-1H-1,2,4-트리아졸-3-일]페닐]카르바메이트]-α-L-만노피라노스 (US 2014/0275503 A1로부터 공지됨) (CAS 1181213-14-8); 8-(2-시클로프로필메톡시-4-트리플루오로메틸-페녹시)-3-(6-트리플루오로메틸-피리다진-3-일)-3-아자-비시클로[3.2.1]옥탄 (CAS 1253850-56-4), (8-anti)-8-(2-시클로프로필메톡시-4-트리플루오로메틸-페녹시)-3-(6-트리플루오로메틸-피리다진-3-일)-3-아자-비시클로[3.2.1]옥탄 (CAS 933798-27-7), (8-syn)-8-(2-시클로프로필메톡시-4-트리플루오로메틸-페녹시)-3-(6-트리플루오로메틸-피리다진-3-일)-3-아자-비시클로[3.2.1]옥탄 (WO 2007040280 A1, WO 2007040282 A1로부터 공지됨) (CAS 934001-66-8), N-[3-클로로-1-(3-피리디닐)-1H-피라졸-4-일]-N-에틸-3-[(3,3,3-트리플루오로프로필)티오]-프로판아미드 (WO 2015/058021 A1, WO 2015/058028 A1로부터 공지됨) (CAS 1477919-27-9) 및 N-[4-(아미노티옥소메틸)-2-메틸-6-[(메틸아미노)카르보닐]페닐]-3-브로모-1-(3-클로로-2-피리디닐)-1H-피라졸-5-카르복스아미드 (CN 103265527 A로부터 공지됨) (CAS 1452877-50-7), 5-(1,3-디옥산-2-일)-4-[[4-(트리플루오로메틸)페닐]메톡시]-피리미딘 (WO 2013/115391 A1로부터 공지됨) (CAS 1449021-97-9), 3-(4-클로로-2,6-디메틸페닐)-4-히드록시-8-메톡시-1-메틸-1,8-디아자스피로[4.5]데스-3-엔-2-온 (WO 2010/066780 A1, WO 2011/151146 A1로부터 공지됨) (CAS 1229023-34-0), 3-(4-클로로-2,6-디메틸페닐)-8-메톡시-1-메틸-1,8-디아자스피로[4.5]데칸-2,4-디온 (WO 2014/187846 A1로부터 공지됨) (CAS 1638765-58-8), 3-(4-클로로-2,6-디메틸페닐)-8-메톡시-1-메틸-2-옥소-1,8-디아자스피로[4.5]데스-3-엔-4-일-탄산 에틸 에스테르 (WO 2010/066780 A1, WO 2011151146 A1로부터 공지됨) (CAS 1229023-00-0), N-[1-[(6-클로로-3-피리디닐)메틸]-2(1H)-피리디닐리덴]-2,2,2-트리플루오로-아세트아미드 (DE 3639877 A1, WO 2012029672 A1로부터 공지됨) (CAS 1363400-41-2), [N(E)]-N-[1-[(6-클로로-3-피리디닐)메틸]-2(1H)-피리디닐리덴]-2,2,2-트리플루오로-아세트아미드, (WO 2016005276 A1로부터 공지됨) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-클로로-3-피리디닐)메틸]-2(1H)-피리디닐리덴]-2,2,2-트리플루오로-아세트아미드, (CAS 1702305-40-5), 3-엔도-3-[2-프로폭시-4-(트리플루오로메틸)페녹시]-9-[[5-(트리플루오로메틸)-2-피리디닐]옥시]-9-아자비시클로[3.3.1]노난 (WO 2011/105506 A1, WO 2016/133011 A1로부터 공지됨) (CAS 1332838-17-1).
본 발명의 화합물(들) 및 조성물과 혼합될 수 있는 완화제의 예는 예를 들어 베녹사코르, 클로퀸토세트 (-멕실), 시오메트리닐, 시프로술파미드, 디클로르미드, 펜클로라졸 (-에틸), 펜클로림, 플루라졸, 플룩소페님, 푸릴라졸, 이속사디펜 (-에틸), 메펜피르 (-디에틸), 나프탈산 무수물, 옥사베트리닐, 2-메톡시-N-({4-[(메틸카르바모일)아미노]페닐}술포닐)벤즈아미드 (CAS 129531-12-0), 4-(디클로로아세틸)-1-옥사-4-아자스피로[4.5]데칸 (CAS 71526-07-3), 2,2,5-트리메틸-3-(디클로로아세틸)-1,3-옥사졸리딘 (CAS 52836-31-4)이다.
본 발명의 화합물(들) 및 조성물과 혼합될 수 있는 제초제의 예는 하기와 같다:
아세토클로르, 아시플루오르펜, 아시플루오르펜-소듐, 아클로니펜, 알라클로르, 알리도클로르, 알록시딤, 알록시딤-소듐, 아메트린, 아미카르바존, 아미도클로르, 아미도술푸론, 4-아미노-3-클로로-6-(4-클로로-2-플루오로-3-메틸페닐)-5-플루오로피리딘-2-카르복실산, 아미노시클로피라클로르, 아미노시클로피라클로르-포타슘, 아미노시클로피라클로르-메틸, 아미노피랄리드, 아미트롤, 암모늄술파메이트, 아닐로포스, 아술람, 아트라진, 아자페니딘, 아짐술푸론, 베플루부타미드, 베나졸린, 베나졸린-에틸, 벤플루랄린, 벤푸레세이트, 벤술푸론, 벤술푸론-메틸, 벤술리드, 벤타존, 벤조비시클론, 벤조페납, 비시클로피론, 비페녹스, 빌라나포스, 빌라나포스-소듐, 비스피리박, 비스피리박-소듐, 브로마실, 브로모부티드, 브로모페녹심, 브로목시닐, 브로목시닐-부티레이트, -포타슘, -헵타노에이트, 및 -옥타노에이트, 부속시논, 부타클로르, 부타페나실, 부타미포스, 부테나클로르, 부트랄린, 부트록시딤, 부틸레이트, 카펜스트롤, 카르베타미드, 카르펜트라존, 카르펜트라존-에틸, 클로람벤, 클로르브로무론, 클로르페낙, 클로르페낙-소듐, 클로르펜프로프, 클로르플루레놀, 클로르플루레놀-메틸, 클로리다존, 클로리무론, 클로리무론-에틸, 클로로프탈림, 클로로톨루론, 클로르탈-디메틸, 클로르술푸론, 시니돈, 시니돈-에틸, 신메틸린, 시노술푸론, 클라시포스, 클레토딤, 클로디나포프, 클로디나포프-프로파르길, 클로마존, 클로메프로프, 클로피랄리드, 클로란술람, 클로란술람-메틸, 쿠밀루론, 시안아미드, 시아나진, 시클로에이트, 시클로피리모레이트, 시클로술파무론, 시클록시딤, 시할로포프, 시할로포프-부틸, 시프라진, 2,4-D, 2,4-D-부토틸, -부틸, -디메틸암모늄, -디올라민, -에틸, -2-에틸헥실, -이소부틸, -이소옥틸, -이소프로필암모늄, -포타슘, -트리이소프로판올암모늄, 및 -트롤아민, 2,4-DB, 2,4-DB-부틸, -디메틸암모늄, -이소옥틸, -포타슘, 및 -소듐, 다이무론 (딤론), 달라폰, 다조메트, n-데칸올, 데스메디팜, 데토실-피라졸레이트 (DTP), 디캄바, 디클로베닐, 2-(2,4-디클로로벤질)-4,4-디메틸-1,2-옥사졸리딘-3-온, 2-(2,5-디클로로벤질)-4,4-디메틸-1,2-옥사졸리딘-3-온, 디클로르프로프, 디클로르프로프-P, 디클로포프, 디클로포프-메틸, 디클로포프-P-메틸, 디클로술람, 디펜조쿼트, 디플루페니칸, 디플루펜조피르, 디플루펜조피르-소듐, 디메푸론, 디메피페레이트, 디메타클로르, 디메타메트린, 디메테나미드, 디메테나미드-P, 디메트라술푸론, 디니트라민, 디노테르브, 디페나미드, 디쿼트, 디쿼트-디브로미드, 디티오피르, 디우론, DNOC, 엔도탈, EPTC, 에스프로카르브, 에탈플루랄린, 에타메트술푸론, 에타메트술푸론-메틸, 에티오진, 에토푸메세이트, 에톡시펜, 에톡시펜-에틸, 에톡시술푸론, 에토벤자니드, F-9600, F-5231, 즉 N-{2-클로로-4-플루오로-5-[4-(3-플루오로프로필)-5-옥소-4,5-디히드로-1H-테트라졸-1-일]페닐}에탄술폰아미드, F-7967, 즉 3-[7-클로로-5-플루오로-2-(트리플루오로메틸)-1H-벤즈이미다졸-4-일]-1-메틸-6-(트리플루오로메틸)피리미딘-2,4(1H,3H)-디온, 페녹사프로프, 페녹사프로프-P, 페녹사프로프-에틸, 페녹사프로프-P-에틸, 페녹사술폰, 펜퀴노트리온, 펜트라자미드, 플람프로프, 플람프로프-M-이소프로필, 플람프로프-M-메틸, 플라자술푸론, 플로라술람, 플루아지포프, 플루아지포프-P, 플루아지포프-부틸, 플루아지포프-P-부틸, 플루카르바존, 플루카르바존-소듐, 플루세토술푸론, 플루클로랄린, 플루페나세트, 플루펜피르, 플루펜피르-에틸, 플루메트술람, 플루미클로락, 플루미클로락-펜틸, 플루미옥사진, 플루오메투론, 플루레놀, 플루레놀-부틸, -디메틸암모늄 및 -메틸, 플루오로글리코펜, 플루오로글리코펜-에틸, 플루프로파네이트, 플루피르술푸론, 플루피르술푸론-메틸-소듐, 플루리돈, 플루로클로리돈, 플루록시피르, 플루록시피르-멥틸, 플루르타몬, 플루티아세트, 플루티아세트-메틸, 포메사펜, 포메사펜-소듐, 포람술푸론, 포사민, 글루포시네이트, 글루포시네이트-암모늄, 글루포시네이트-P-소듐, 글루포시네이트-P-암모늄, 글루포시네이트-P-소듐, 글리포세이트, 글리포세이트-암모늄, -이소프로필암모늄, -디암모늄, -디메틸암모늄, -포타슘, -소듐, 및 -트리메슘, H-9201, 즉 O-(2,4-디메틸-6-니트로페닐) O-에틸 이소프로필포스포르아미도티오에이트, 할라욱시펜, 할라욱시펜-메틸, 할로사펜, 할로술푸론, 할로술푸론-메틸, 할록시포프, 할록시포프-P, 할록시포프-에톡시에틸, 할록시포프-P-에톡시에틸, 할록시포프-메틸, 할록시포프-P-메틸, 헥사지논, HW-02, 즉 1-(디메톡시포스포릴) 에틸-(2,4-디클로로페녹시)아세테이트, 이마자메타벤즈, 이마자메타벤즈-메틸, 이마자목스, 이마자목스-암모늄, 이마자픽, 이마자픽-암모늄, 이마자피르, 이마자피르-이소프로필암모늄, 이마자퀸, 이마자퀸-암모늄, 이마제타피르, 이마제타피르-임모늄, 이마조술푸론, 인다노판, 인다지플람, 아이오도술푸론, 아이오도술푸론-메틸-소듐, 이옥시닐, 이옥시닐-옥타노에이트, -포타슘 및 -소듐, 이프펜카르바존, 이소프로투론, 이소우론, 이속사벤, 이속사플루톨, 카르부틸레이트, KUH-043, 즉 3-({[5-(디플루오로메틸)-1-메틸-3-(트리플루오로메틸)-1H-피라졸-4-일]메틸}술포닐)-5,5-디메틸-4,5-디히드로-1,2-옥사졸, 케토스피라독스, 락토펜, 레나실, 리누론, MCPA, MCPA-부토틸, -디메틸암모늄, -2-에틸헥실, -이소프로필암모늄, -포타슘, 및 -소듐, MCPB, MCPB-메틸, -에틸 및 -소듐, 메코프로프, 메코프로프-소듐, 및 -부토틸, 메코프로프-P, 메코프로프-P-부토틸, -디메틸암모늄, -2-에틸헥실, 및 -포타슘, 메페나세트, 메플루이디드, 메소술푸론, 메소술푸론-메틸, 메소트리온, 메타벤즈티아주론, 메탐, 메타미포프, 메타미트론, 메타자클로르, 메타조술푸론, 메타벤즈티아주론, 메티오피르술푸론, 메티오졸린, 메틸 이소티오시아네이트, 메토브로무론, 메톨라클로르, S-메톨라클로르, 메토술람, 메톡수론, 메트리부진, 메트술푸론, 메트술푸론-메틸, 몰리네이트, 모노리누론, 모노술푸론, 모노술푸론-에스테르, MT-5950, 즉 N-(3-클로로-4-이소프로필페닐)-2-메틸펜탄 아미드, NGGC-011, 나프로파미드, NC-310, 즉 [5-(벤질옥시)-1-메틸-1H-피라졸-4-일](2,4-디클로로페닐)메타논, 네부론, 니코술푸론, 노난산 (펠라르곤산), 노르플루라존, 올레산 (지방산), 오르벤카르브, 오르토술파무론, 오리잘린, 옥사디아르길, 옥사디아존, 옥사술푸론, 옥사지클로메폰, 옥시플루오르펜, 파라쿼트, 파라쿼트 디클로라이드, 페불레이트, 펜디메탈린, 페녹스술람, 펜타클로로페놀, 펜톡사존, 페톡사미드, 석유 오일, 펜메디팜, 피클로람, 피콜리나펜, 피녹사덴, 피페로포스, 프레틸라클로르, 프리미술푸론, 프리미술푸론-메틸, 프로디아민, 프로폭시딤, 프로메톤, 프로메트린, 프로파클로르, 프로파닐, 프로파퀴자포프, 프로파진, 프로팜, 프로피소클로르, 프로폭시카르바존, 프로폭시카르바존-소듐, 프로피리술푸론, 프로피자미드, 프로술포카르브, 프로술푸론, 피라클로닐, 피라플루펜, 피라플루펜-에틸, 피라술포톨, 피라졸리네이트 (피라졸레이트), 피라조술푸론, 피라조술푸론-에틸, 피라족시펜, 피리밤벤즈, 피리밤벤즈-이소프로필, 피리밤벤즈-프로필, 피리벤족심, 피리부티카르브, 피리다폴, 피리데이트, 피리프탈리드, 피리미노박, 피리미노박-메틸, 피리미술판, 피리티오박, 피리티오박-소듐, 피록사술폰, 피록스술람, 퀸클로락, 퀸메락, 퀴노클라민, 퀴잘로포프, 퀴잘로포프-에틸, 퀴잘로포프-P, 퀴잘로포프-P-에틸, 퀴잘로포프-P-테푸릴, 림술푸론, 사플루페나실, 세톡시딤, 시두론, 시마진, 시메트린, SL-261, 술코트리온, 술펜트라존, 술포메투론, 술포메투론-메틸, 술포술푸론, SYN-523, SYP-249, 즉 1-에톡시-3-메틸-1-옥소부트-3-엔-2-일 5-[2-클로로-4-(트리플루오로메틸)페녹시]-2-니트로벤조에이트, SYP-300, 즉 1-[7-플루오로-3-옥소-4-(프로프-2-인-1-일)-3,4-디히드로-2H-1,4-벤족사진-6-일]-3-프로필-2-티옥소이미다졸리딘-4,5-디온, 2,3,6-TBA, TCA (트리클로로아세트산), TCA-소듐, 테부티우론, 테푸릴트리온, 템보트리온, 테프랄록시딤, 테르바실, 테르부카르브, 테르부메톤, 테르부틸라진, 테르부트린, 테닐클로르, 티아조피르, 티엔카르바존, 티엔카르바존-메틸, 티펜술푸론, 티펜술푸론-메틸, 티오벤카르브, 티아페나실, 톨피랄레이트, 토프라메존, 트랄콕시딤, 트리아파몬, 트리-알레이트, 트리아술푸론, 트리아지플람, 트리베누론, 트리베누론-메틸, 트리클로피르, 트리에타진, 트리플록시술푸론, 트리플록시술푸론-소듐, 트리플루디목사진, 트리플루랄린, 트리플루술푸론, 트리플루술푸론-메틸, 트리토술푸론, 우레아 술페이트, 베르놀레이트, XDE-848, ZJ-0862, 즉 3,4-디클로로-N-{2-[(4,6-디메톡시피리미딘-2-일)옥시]벤질}아닐린, 및 하기 화합물:
식물 성장 조절제의 예는 하기와 같다:
아시벤졸라르, 아시벤졸라르-S-메틸, 5-아미노레불린산, 안시미돌, 6-벤질아미노퓨린, 브라시놀리드, 카테킨, 클로르메쿼트 클로라이드, 클로프로프, 시클라닐리드, 3-(시클로프로프-1-에닐) 프로피온산, 다미노지드, 다조메트, n-데칸올, 디케굴락, 디케굴락-소듐, 엔도탈, 엔도탈-디포타슘, -디소듐, 및 -모노(N,N-디메틸알킬암모늄), 에테폰, 플루메트랄린, 플루레놀, 플루레놀-부틸, 플루르프리미돌, 포르클로르페누론, 지베렐산, 이나벤피드, 인돌-3-아세트산 (IAA), 4-인돌-3-일부티르산, 이소프로티올란, 프로베나졸, 자스몬산, 말레산 히드라지드, 메피쿼트 클로라이드, 1-메틸시클로프로펜, 메틸 자스모네이트, 2-(1-나프틸)아세트아미드, 1-나프틸아세트산, 2-나프틸옥시아세트산, 니트로페놀레이트-혼합물, 파클로부트라졸, N-(2-페닐에틸)-베타-알라닌, N-페닐프탈람산, 프로헥사디온, 프로헥사디온-칼슘, 프로히드로자스몬, 살리실산, 스트리고락톤, 테크나젠, 티디아주론, 트리아콘탄올, 트리넥사팍, 트리넥사팍-에틸, 시토데프, 유니코나졸, 유니코나졸-P.
방법 및 용도
본 발명의 화합물(들) 및 조성물은 강력한 식물 방어 조정 잠재력을 갖는다. 이들은 원치 않는 박테리아, 특히 크산토모나스 속의 박테리아를 방제하는 데 사용될 수 있다. 본 발명의 화합물(들) 및 조성물은 종자, 발아 종자, 출아 묘목, 식물, 식물 부분, 과실, 수확품 및/또는 식물이 성장하는 토양을 보호하는 데 사용될 수 있다.
본원에 사용된 바와 같은 방제 또는 방제하는 것은 원치 않는 미생물의 예방적, 보호적, 치유적 및 근절적 치료를 포괄한다.
따라서, 본 발명은 본 발명의 적어도 1종의 화합물 또는 본 발명의 적어도 1종의 조성물을 식물, 식물 부분, 종자, 과실 또는 식물이 성장하는 토양에 적용하는 단계를 포함하는, 크산토모나스 속의 박테리아에 의해 유발된 박테리아성 질병을 방제하는 방법에 관한 것이다.
전형적으로, 본 발명의 화합물(들) 및 조성물이 박테리아성 질병을 방제하기 위한 치유적 또는 보호적 방법에 사용되는 경우에, 그의 효과적이고 식물-상용성인 양이 식물, 식물 부분, 과실, 종자 또는 식물이 성장하는 토양 또는 기재에 적용된다. 식물을 재배하는 데 사용될 수 있는 적합한 기재는 무기 기반 기재, 예컨대 미네랄 울, 특히 스톤 울, 펄라이트, 모래 또는 자갈; 유기 기재, 예컨대 토탄, 소나무 목피 또는 톱밥; 및 석유 기반 기재, 예컨대 중합체 발포체 또는 플라스틱 비드를 포함한다. 효과적이고 식물-상용성인 양은 농경지 상에 존재하거나 또는 나타나기 쉬운 박테리아를 방제하는 데 충분하고, 상기 작물에 대한 식물독성의 임의의 인지가능한 증상을 수반하지 않는 양을 의미한다. 이러한 양은 방제될 병원체, 작물의 유형, 작물 성장 단계, 기후 조건 및 사용된 본 발명의 각각의 화합물(들) 또는 조성물에 따라 넓은 범위 내에서 달라질 수 있다. 이러한 양은 관련 기술분야의 통상의 기술자의 능력 내에 있는, 체계적인 현장 시험에 의해 결정될 수 있다. 박테리아성 병원체, 예를 들어 크산토모나스 종 (예를 들어 크산토모나스 캄페스트리스 병원체변종 오리자에), 슈도모나스 종 (예를 들어 슈도모나스 시린가에 병원체변종 라크리만스(Pseudomonas syringae pv. Lachrymans)), 에르위니아(Erwinia) 종 (예를 들어 에르위니아 아밀로보라(Erwinia amylovora))에 의해 유발된 질병은 본 발명의 화합물에 의해 방제될 수 있다. 화학식 (III)의 화합물은 또한 식물 상의 식물병원성 진균을 방제하는 데 효율적일 수 있다.
식물 및 식물 부분
본 발명의 화합물(들) 및 조성물은 임의의 식물 또는 식물 부분에 적용될 수 있다.
식물은 모든 식물 및 식물 군집, 예컨대 목적하는 및 목적하지 않는 야생 식물 또는 작물 식물 (자연 발생 작물 식물 포함)을 의미한다. 작물 식물은 통상의 육종 및 최적화 방법에 의해 또는 생명공학 및 유전 공학 방법 또는 이들 방법의 조합에 의해 수득될 수 있는 식물일 수 있으며, 유전자 변형 식물 (GMO 또는 트랜스제닉 식물)을 포함하고, 식물 육종가의 권리에 의해 보호가능한 및 보호불가능한 식물 재배품종을 포함할 수 있다.
유전자 변형 식물 (GMO)
유전자 변형 식물 (GMO 또는 트랜스제닉 식물)은 이종 유전자가 게놈에 안정적으로 통합된 식물이다. 표현 "이종성 유전자"는 본질적으로 핵, 엽록체 또는 미토콘드리아 게놈에 도입될 때 식물 외부에서 제공 또는 조립된 유전자를 의미한다. 이러한 유전자는 관심 단백질 또는 폴리펩티드를 발현시키거나 또는 식물에 존재하는 다른 유전자(들)를 하향조절 또는 침묵시킴으로써 (예를 들어, 안티센스 기술, 공동억제 기술, RNA 간섭 - RNAi - 기술 또는 마이크로RNA - miRNA - 기술을 사용함), 형질전환된 식물에 새롭거나 개선된 농경학적 또는 다른 특성을 제공한다. 게놈 내에 위치하는 이종 유전자는 트랜스진으로도 칭해진다. 식물 게놈 내에서의 이의 특정 위치에 의해 정의되는 트랜스진은 형질전환 또는 트랜스제닉 이벤트로 칭해진다.
식물 재배품종은 새로운 성질 ("형질")을 갖고 통상적인 육종, 돌연변이유발 또는 재조합 DNA 기술에 의해 수득된 식물을 의미하는 것으로 이해된다. 이는 재배품종, 변종, 생물형 또는 유전자형일 수 있다.
식물 부분은 지면의 위 아래의 식물의 모든 부분 및 기관, 예컨대 싹, 잎, 가시, 대, 줄기, 꽃, 과실체, 과실, 종자, 뿌리, 괴경 및 근경을 의미한다. 식물 부분은 또한 수확된 물질 및 영양 및 생식 번식 물질, 예를 들어 묘목, 괴경, 근경, 자른 가지 및 종자를 포함한다.
본 발명의 방법에 따라 처리될 수 있는 식물은 하기를 포함한다: 목화, 아마, 포도덩굴, 과일, 채소, 예컨대 로사세아에 종 (예를 들어 인과류 예컨대 사과 및 배, 또한 핵과류 예컨대 살구, 체리, 아몬드 및 복숭아, 및 장과류 예컨대 딸기), 리베시오이다에(Ribesioidae) 종, 주글란다세아에(Juglandaceae) 종, 베툴라세아에(Betulaceae) 종, 아나카르디아세아에(Anacardiaceae) 종, 파가세아에(Fagaceae) 종, 모라세아에(Moraceae) 종, 올레아세아에(Oleaceae) 종, 악티니다세아에(Actinidaceae) 종, 라우라세아에(Lauraceae) 종, 무사세아에(Musaceae) 종 (예를 들어 바나나 나무 및 농장), 루비아세아에(Rubiaceae) 종 (예를 들어 커피), 테아세아에(Theaceae) 종, 스테르쿨리세아에(Sterculiceae) 종, 루타세아에(Rutaceae) 종 (예를 들어 레몬, 오렌지 및 그레이프프루트); 솔라나세아에(Solanaceae) 종 (예를 들어 토마토), 릴리아세아에(Liliaceae) 종, 아스테라세아에(Asteraceae) 종 (예를 들어 상추), 움벨리페라에(Umbelliferae) 종, 크루시페라에(Cruciferae) 종, 케노포디아세아에(Chenopodiaceae) 종, 쿠쿠르비타세아에(Cucurbitaceae) 종 (예를 들어 오이), 알리아세아에(Alliaceae) 종 (예를 들어 리크, 양파), 파필리오나세아에(Papilionaceae) 종 (예를 들어 완두); 주요 작물 식물, 예컨대 그라미네아에(Gramineae) 종 (예를 들어 옥수수, 잔디, 곡류 예컨대 밀, 호밀, 벼, 보리, 귀리, 기장 및 트리티케일), 아스테라세아에(Asteraceae) 종 (예를 들어 해바라기), 브라시카세아에(Brassicaceae) 종 (예를 들어 백색 양배추, 적색 양배추, 브로콜리, 콜리플라워, 브뤼셀 스프라우트, 청경채, 콜라비, 무, 및 유지종자 평지, 겨자, 호스래디시 및 큰다닥냉이), 파바카에(Fabacae) 종 (예를 들어 콩, 땅콩), 파필리오나세아에(Papilionaceae) 종 (예를 들어 대두), 솔라나세아에(Solanaceae) 종 (예를 들어 감자), 케노포디아세아에(Chenopodiaceae) 종 (예를 들어 사탕무, 사료용 비트, 근대, 비트); 정원 및 수목지에 유용한 식물 및 관상 식물; 및 이들 식물 각각의 유전자 변형 품종.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종은 1종 이상의 생물적 스트레스에 대해 저항성인 식물 및 식물 재배품종을 포함하며, 즉 상기 식물은 동물 및 미생물 해충, 예컨대 선충류, 곤충, 응애, 식물병원성 진균, 박테리아, 바이러스 및/또는 바이로이드에 대해 보다 우수한 방어를 나타낸다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종은 1종 이상의 비생물적 스트레스에 저항성인 식물을 포함한다. 비생물적 스트레스 조건은, 예를 들어 가뭄, 저온 노출, 열 노출, 삼투 스트레스, 홍수, 토양 염도 증가, 미네랄 노출 증가, 오존 노출, 고도의 광 노출, 제한된 질소 영양소 이용성, 제한된 인 영양소 이용성, 음지 회피를 포함할 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종은 증진된 수확량 특징을 특징으로 하는 식물을 포함한다. 상기 식물에서의 수확량 증가는, 예를 들어 식물 생리학, 성장 및 발육, 예컨대 물 사용 효율, 수분 저류 효율의 개선, 질소 사용 개선, 탄소 동화 증진, 광합성 개선, 발아 효율 증가 및 성숙 가속화의 결과일 수 있다. 수확량은 (스트레스 및 비스트레스 조건 하에서), 조기 개화, 하이브리드 종자 생산을 위한 개화 조절, 묘목 활력, 식물 크기, 절간(internode) 수 및 거리, 뿌리 성장, 종자 크기, 과실 크기, 꼬투리 크기, 꼬투리 또는 이삭 수, 꼬투리 또는 이삭 당 종자 수, 종자 질량, 종자 충실률 증진, 종자 분산 감소, 꼬투리 열개 감소 및 도복 저항성을 포함하나 이에 제한되지는 않는 개선된 식물 아키텍쳐(architecture)에 또한 영향을 받을 수 있다. 추가의 수확량 형질은 종자 조성, 예컨대 탄수화물 함량 및 조성, 예를 들어 목화 또는 전분, 단백질 함량, 오일 함량 및 조성, 영양가, 반-영양 화합물의 감소, 개선된 가공성 및 보다 우수한 저장 안정성을 포함한다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종은 일반적으로 보다 높은 수확량, 활력, 건강 및 생물적 및 비생물적 스트레스에 대한 저항성을 유발하는 잡종강세 또는 하이브리드 활력의 특징을 이미 발현하는 하이브리드 식물인 식물 및 식물 재배품종을 포함한다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 제초제-내성 식물, 즉 1종 이상의 주어진 제초제에 대해 내성이 생긴 식물인 식물 및 식물 재배품종을 포함한다. 이러한 식물은 유전자 형질전환에 의해 또는 이러한 제초제 내성을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 곤충-저항성 트랜스제닉 식물, 즉 특정의 표적 곤충에 의한 공격에 대해 저항성이 생긴 식물인 식물 및 식물 재배품종을 포함한다. 이러한 식물은 유전자 형질전환에 의해, 또는 이러한 곤충 저항성을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 질병-저항성 트랜스제닉 식물, 즉 특정의 표적 곤충에 의한 공격에 대해 저항성이 생긴 식물인 식물 및 식물 재배품종을 포함한다. 이러한 식물은 유전자 형질전환에 의해, 또는 이러한 곤충 저항성을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 비생물적 스트레스에 내성인 식물 및 식물 재배품종을 포함한다. 이러한 식물은 유전자 형질전환에 의해 또는 이러한 스트레스 저항성을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 수확된 산물의 변경된 양, 품질 및/또는 저장-안정성 및/또는 수확된 산물의 특정 성분의 변경된 특성을 나타내는 식물 및 식물 재배품종을 포함한다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 변경된 섬유 특징을 갖는 식물 및 식물 재배품종, 예컨대 목화 식물을 포함한다. 이러한 식물은 유전자 형질전환에 의해 또는 이러한 변경된 섬유 특성을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 변경된 오일 프로파일 특징을 갖는 식물 및 식물 재배품종, 예컨대 유지종자 평지 또는 관련 브라시카 식물을 포함한다. 이러한 식물은 유전자 형질전환에 의해 또는 이러한 변경된 오일 프로파일 특성을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 변경된 종자 탈립 특징을 갖는 식물 및 식물 재배품종, 예컨대 유지종자 평지 또는 관련 브라시카 식물을 포함한다. 이러한 식물은 유전자 형질전환에 의해 또는 이러한 변경된 종자 탈립 특징을 부여하는 돌연변이를 함유하는 식물의 선택에 의해 수득될 수 있고, 지연된 또는 감소된 종자 탈립을 갖는 식물, 예컨대 유지종자 평지 식물을 포함한다.
상기 개시된 방법에 의해 처리될 수 있는 식물 및 식물 재배품종 (식물 생명공학 방법, 예컨대 유전 공학에 의해 수득됨)은 변경된 번역후 단백질 변형 패턴을 갖는 식물 및 식물 재배품종, 예컨대 담배 식물을 포함한다.
본 교시의 측면들은 하기 실시예의 관점에서 추가로 이해될 수 있고, 하기 실시예는 어떠한 방식으로도 본 교시의 범주를 제한하는 것으로서 간주되어서는 안된다.
실시예
제조 실시예 1: 5-(4,5-디브로모-3-플루오로-2-티에닐)-6-옥사-4-아자스피로[2.4]헵트-4-엔-7-온 (화합물 III.01)의 제조
단계 1: 에틸 1-{[(4,5-디브로모-3-플루오로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.01)의 제조
테트라히드로푸란 3 mL 중에 용해시킨 4,5-디브로모-3-플루오로티오펜-2-카르복실산 200 mg (0.66 mmol) 및 에틸 1-아미노시클로프로판카르복실레이트 히드로클로라이드 (1:1) 170 mg (1.32 mmol)의 용액에 트리에틸아민 0.14 mL (1.00 mmol)에 이어서 에틸 아세테이트 중 50% (w/w) 프로판포스폰산 무수물 용액 0.59 mL (1.00 mmol)를 첨가하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. 반응 혼합물을 물로 켄칭하고, 에틸 아세테이트로 추출하였다. 합한 유기 층을 황산마그네슘 상에서 건조시키고, 여과하고, 감압 하에 농축시켰다. 잔류물을 실리카 겔 상에서 칼럼 크로마토그래피 (구배 n-헵탄/에틸 아세테이트)에 의해 정제하여 에틸 1-{[(4,5-디브로모-3-플루오로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 230 mg (83% 순도, 70% 수율)을 수득하였다. LogP = 3.15. (M+H) = 414.
단계 2: 1-{[(4,5-디브로모-3-플루오로-2-티에닐)카르보닐]아미노}시클로프로판카르복실산 (화합물 XXI.03)의 제조
테트라히드로푸란 3 mL 중에 용해시킨 에틸 1-{[(4,5-디브로모-3-플루오로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 239 mg (0.58 mmol)의 용액에 1 M 수성 수산화리튬 용액 1.15 mL (1.15 mmol)를 첨가하였다. 반응물을 실온에서 1시간 동안 교반하였다. 이어서, 반응 혼합물을 80℃에서 30분 동안 가열하였다. 반응 혼합물을 물로 희석하고, 1 M 수성 염산 용액으로 조심스럽게 산성화시켰다. 수성 층을 에틸 아세테이트로 추출하였다. 합한 유기 층을 황산마그네슘 상에서 건조시키고, 여과하고, 감압 하에 농축시켜 1-{[(4,5-디브로모-3-플루오로-2-티에닐)카르보닐]아미노}시클로프로판카르복실산 158 mg (90% 순도, 64% 수율)을 수득하였다. LogP = 2.15. (M+H) = 408.
단계 3: 5-(4,5-디브로모-3-플루오로-2-티에닐)-6-옥사-4-아자스피로[2.4]헵트-4-엔-7-온 (화합물 III.01)의 제조
디클로로메탄 50 mL 중 1-{[(4,5-디브로모-3-플루오로-2-티에닐)카르보닐] 아미노}시클로프로판카르복실산 1.15 g (2.97 mmol)의 현탁액에 몇 방울의 N,N-디메틸포름아미드에 이어서 옥살릴 클로라이드 0.31 mL (3.57 mmol)를 첨가하였다. 반응물을 실온에서 1시간 동안 교반하였다. 반응 혼합물을 물로 켄칭하고, 디클로로메탄으로 추출하였다. 합한 유기 층을 황산마그네슘 상에서 건조시키고, 여과하고, 감압 하에 농축시켰다. 잔류물을 실리카 겔 상에서 칼럼 크로마토그래피 (구배 n-헵탄/에틸 아세테이트)에 의해 정제하여 5-(4,5-디브로모-3-플루오로-2-티에닐)-6-옥사-4-아자스피로[2.4]헵트-4-엔-7-온 270 mg (98% 순도, 23% 수율)을 수득하였다. LogP = 3.58. (M+H) = 368.
제조 실시예 2: 중간체 에틸 1-{[(4,5-디클로로-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.11)의 제조
5 mL 마이크로웨이브 바이알에서 불활성 분위기 하에, 에틸 1-{[(4,5-디클로로-3-아이오도-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.08) 100 mg (0.23 mmol), 메틸보론산 21 mg (0.34 mmol), 아세트산팔라듐 (II) 2.6 mg (0.01 mmol), 트리시클로헥실포스핀 6.5 mg (0.02 mmol) 및 삼염기성 인산칼륨 172 mg (0.80 mmol)을 연속적으로 첨가하고, 이어서 탈기된 톨루엔 (1.25 mL) 및 물 (0.13 mL)을 첨가하였다. 바이알을 밀봉하고, 반응 혼합물을 100℃에서 18시간 동안 교반하였다. 반응 혼합물을 물로 희석하고, 디클로로메탄으로 추출하였다. 합한 유기 층을 켐 일루트(Chem Elut)™ 카트리지를 통해 여과하고, 감압 하에 농축시켰다. 잔류물을 실리카 겔 상에서 칼럼 크로마토그래피 (구배 n-헵탄/에틸 아세테이트)에 의해 정제하여 에틸 1-{[(4,5-디클로로-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 29 mg (100% 순도, 39% 수율)을 백색 고체로서 수득하였다. LogP = 3.16. (M+H) = 322.
제조 실시예 3: 중간체 에틸 1-{[(3,4,5-트리클로로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.05)의 제조
단계 1: 에틸 1-{[(3-아미노-4,5-디클로로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXVIII.01)의 제조
디클로로메탄 4.0 mL 중에 용해시킨 3-아미노-4,5-디클로로티오펜-2-카르복실산 히드로클로라이드 (1:1) (화합물 XXXa.02) 150 mg (0.60 mmol) 및 에틸 1-아미노시클로프로판카르복실레이트 히드로클로라이드 (1:1) 255 mg (1.50 mmol)의 용액에 N,N-디이소프로필에틸아민 0.45 mL (2.59 mmol)에 이어서 디클로로메탄 2.0 mL 중 2-클로로-1,3-디메틸이미다졸리늄 클로라이드 255 mg (1.50 mmol)의 용액을 첨가하였다. 반응 혼합물을 실온에서 16시간 동안 교반하였다. 반응 혼합물을 물로 켄칭하고, 디클로로메탄으로 추출하였다. 합한 유기 층을 황산마그네슘 상에서 건조시키고, 여과하고, 감압 하에 농축시켰다. 잔류물을 정제용 고성능 액체 크로마토그래피 (구배 아세토니트릴/포름산 (1%)의 수용액)에 의해 정제하여 에틸 1-{[(3-아미노-4,5-디클로로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 69 mg (100% 순도, 35% 수율)을 백색 고체로서 수득하였다. LogP = 2.77. (M+H) = 323.
단계 2: 에틸 1-{[(3,4,5-트리클로로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.05)의 제조
무수 아세토니트릴 0.5 mL 중 염화구리 (I) (9.8 mg, 0.10 mmol)의 용액에 tert-부틸 니트라이트 (13 μL, 0.10 mmol)를 0℃에서 적가하였다. 반응 혼합물을 실온으로 가온되도록 한 후, 무수 아세토니트릴 0.5 mL 중 에틸 1-{[(3-아미노-4,5-디클로로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 25 mg (0.06 mmol)의 용액을 적가하였다. 반응 혼합물을 실온에서 3시간 동안 교반하였다. 반응 혼합물을 디클로로메탄으로 희석하고, 1 M 수성 염산 용액으로 조심스럽게 산성화시켰다. 수성 층을 디클로로메탄으로 2회 추출하였다. 합한 유기 층을 황산마그네슘 상에서 건조시키고, 여과하고, 감압 하에 농축시켰다. 잔류물을 정제용 고성능 액체 크로마토그래피 (구배 아세토니트릴/포름산 (1%)의 수용액)에 의해 정제하여 에틸 1-{[(3,4,5-트리클로로-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 12 mg (93% 순도, 48% 수율)을 베이지색 고체로서 수득하였다. LogP = 3.40. (M) = 341.
제조 실시예 4: 중간체 에틸 1-{[(4,5-디브로모-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.02)의 제조
단계 1: 에틸 1-[({4-브로모-5-[(tert-부톡시카르보닐)아미노]-3-메틸-2-티에닐}카르보닐)아미노]시클로프로판카르복실레이트 (화합물 XXVa.01)의 제조
디클로로메탄 1.4 mL 중에 용해시킨 4-브로모-5-[(tert-부톡시카르보닐)아미노]-3-메틸티오펜-2-카르복실산 (화합물 XXVIIa.02) 92 mg (0.27 mmol) 및 에틸 1-아미노시클로프로판카르복실레이트 히드로클로라이드 67 mg (0.41 mmol)의 용액에 N,N-디이소프로필에틸아민 0.14 mL (0.82 mmol)에 이어서 1-[비스(디메틸아미노)메틸렌]-1H-1,2,3-트리아졸로[4,5-b]피리디늄 3-옥시드 헥사플루오로포스페이트 135 mg (0.35 mmol)을 첨가하였다. 반응 혼합물을 실온에서 3.5시간 동안 교반하였다. 반응 혼합물을 물로 켄칭하고, 디클로로메탄으로 추출하였다. 합한 유기 층을 켐 일루트™ 카트리지를 통해 여과하고, 감압 하에 농축시켰다. 잔류물을 실리카 겔 상에서 칼럼 크로마토그래피 (구배 n-헵탄/에틸 아세테이트)에 의해 정제하여 에틸 1-[({4-브로모-5-[(tert-부톡시카르보닐)아미노]-3-메틸-2-티에닐}카르보닐)아미노]시클로프로판카르복실레이트 95 mg (93% 순도, 72% 수율)을 오렌지색 고체로서 수득하였다. LogP = 3.28. (M+H) = 447.
단계 2: 에틸 1-{[(5-아미노-4-브로모-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXIVa.01)의 제조
클로로포름 0.60 mL 중 1-[(tert-부톡시카르보닐)아미노]-3-메틸-2-티에닐}카르보닐)아미노]시클로프로판카르복실레이트 60 mg (0.13 mmol)의 용액에 트리플루오로아세트산 0.62 mL를 첨가하였다. 반응물을 실온에서 18시간 동안 교반하였다. 반응 혼합물을 톨루엔으로 희석하고, 감압 하에 농축시켰다. 잔류물을 정제용 고성능 액체 크로마토그래피 (구배 아세토니트릴/아세트산암모늄 (1 mM)의 수용액))에 의해 정제하여 에틸 1-{[(5-아미노-4-브로모-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 35 mg (100% 순도, 74% 수율)을 백색 고체로서 수득하였다. LogP = 1.92. (M+H) = 347.
단계 3: 에틸 1-{[(4,5-디브로모-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 (화합물 XXI.02)의 제조
무수 아세토니트릴 0.5 mL 중 브로민화구리 (II) (28.9 mg, 0.13 mmol)의 용액에 tert-부틸 니트라이트 (17 μL, 0.13 mmol)를 0℃에서 적가하였다. 반응 혼합물을 실온으로 가온되도록 한 후, 무수 아세토니트릴 0.7 mL 중 에틸 1-{[(5-아미노-4-브로모-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 30 mg (0.08 mmol)의 용액을 적가하였다. 반응 혼합물을 실온에서 2시간 동안 교반하였다. 반응 혼합물을 에틸 아세테이트로 희석하고, 1 M 수성 염산 용액으로 조심스럽게 산성화시켰다. 수성 층을 에틸 아세테이트로 3회 추출하였다. 합한 유기 층을 황산마그네슘 상에서 건조시키고, 여과하고, 감압 하에 농축시켰다. 잔류물을 실리카 겔 상에서 칼럼 크로마토그래피 (구배 n-헵탄/에틸 아세테이트)에 의해 정제하여 에틸 1-{[(4,5-디브로모-3-메틸-2-티에닐)카르보닐]아미노}시클로프로판카르복실레이트 11 mg (100% 순도, 31% 수율)을 백색 고체로서 수득하였다. LogP = 3.19. (M+H) = 410.
예시적인 화합물
표 III.1, III.2, III.3, III.4, III.5, III.6 및 III.7에 제시된 바와 같은 본 발명에 따른 화합물을 상기 제공된 실시예와 유사하게 및/또는 본원에 개시된 방법의 일반적 설명에 따라 제조하였다.
하기 표 III.1은 하기 화학식 (III)에 따른 화합물의 실시예를 비제한적 방식으로 예시한다.
표 III.1:
주: Me: 메틸
하기 표에 제시된 바와 같은 본 발명에 따른 중간체를 상기 제공된 실시예와 유사하게 및/또는 본원에 개시된 방법의 일반적 설명에 따라 제조하였다.
하기 표 III.2는 하기 화학식 (XXI)에 따른 중간체의 실시예를 비제한적 방식으로 예시한다.
표 III.2:
주: Me: 메틸, Et: 에틸
하기 표 III.3은 하기 화학식 (XXIIa)에 따른 중간체의 실시예를 비제한적 방식으로 예시한다.
표 III.3:
주: Me: 메틸
하기 표 III.4는 하기 화학식 (XXIVa) 및 (XXVa)에 따른 중간체의 실시예를 비제한적 방식으로 예시한다.
표 III.4:
주: Et: 에틸
하기 표 III.5는 하기 화학식 (XXVIIa)에 따른 중간체의 실시예를 비제한적 방식으로 예시한다.
표 III.5:
주: Me: 메틸, Et: 에틸
하기 표 III.6은 하기 화학식 (XXVIII) 및 (XXIXa)에 따른 중간체의 실시예를 비제한적 방식으로 예시한다.
표 III.6:
주: Et: 에틸
하기 표 III.7은 하기 화학식 (XXXa) 및 (XXXIa)에 따른 중간체의 실시예를 비제한적 방식으로 예시한다.
표 III.7:
주: Me: 메틸; 아세틸: -C(=O)-CH3
상기 표들에서, LogP 값의 측정은 EEC 지침 79/831 부록 V.A8에 따라 HPLC (고성능 액체 크로마토그래피)에 의해 역상 칼럼 상에서 하기 방법으로 수행하였다:
[a] LogP 값은 LC-UV의 측정에 의해, 산성 범위 내에서, 용리액으로서 물 및 아세토니트릴 중 0.1% 포름산 (10% 아세토니트릴에서 95% 아세토니트릴의 선형 구배)을 사용하여 결정한다.
[b] LogP 값은 LC-UV의 측정에 의해, 중성 범위 내에서, 용리액으로서 물 및 아세토니트릴 중 0.001 몰 아세트산암모늄 용액 (10% 아세토니트릴에서 95% 아세토니트릴의 선형 구배)을 사용하여 결정한다.
[c] LogP 값은 LC-UV의 측정에 의해, 산성 범위 내에서, 용리액으로서 0.1% 인산 및 아세토니트릴 (10% 아세토니트릴에서 95% 아세토니트릴의 선형 구배)을 사용하여 결정한다.
1개 초과의 LogP 값이 동일한 방법 내에서 이용가능한 경우, 모든 값이 주어지고 "+"로 분리된다.
보정은 기지의 LogP 값을 갖는 직쇄 알칸2-온 (3 내지 16개의 탄소 원자를 가짐)을 사용하여 수행하였다 (연속적 알카논 사이에 선형 내삽으로 체류 시간을 사용한 LogP 값의 측정). 람다-최대-값은 200 nm 내지 400 nm의 UV-스펙트럼 및 크로마토그래피 신호의 피크 값을 사용하여 결정하였다.
NMR-피크 목록
표 A는 상기 표들에 개시된 일부 화합물의 NMR 데이터 (1H)를 제공한다.
선택된 실시예의 1H-NMR 데이터는 1H-NMR-피크 목록의 형태로 표기된다. 각각의 신호 피크에 대해 δ-값 (ppm) 및 둥근 괄호 안의 신호 강도가 열거된다. δ-값 - 신호 강도 쌍 사이에 구분 기호로서 세미콜론이 존재한다.
따라서, 실시예의 피크 목록은 하기 형태를 갖는다:
δ1 (강도1); δ2 (강도2);........; δi (강도i);......; δn (강도n)
예리한 신호의 강도는 NMR 스펙트럼의 출력된 예에서의 신호의 높이 (cm)와 상관관계가 있고, 신호 강도의 실제 관계를 나타낸다. 넓은 신호로부터 여러 피크 또는 신호의 중간 및 스펙트럼에서의 가장 강한 신호와 비교한 그의 상대 강도가 제시될 수 있다.
1H 스펙트럼에 대한 화학적 이동을 보정하기 위해, 본 발명자들은 테트라메틸실란 및/또는 특히 DMSO 중에서 측정된 스펙트럼의 경우에 사용된 용매의 화학적 이동을 사용한다. 따라서 NMR 피크 목록에서, 테트라메틸실란 피크가 발생할 수 있으나 반드시 그러한 것은 아니다.
1H-NMR 피크 목록은 전형적인 1H-NMR 출력물과 유사하며, 따라서 통상적으로 전형적인 NMR-해석에서 열거되는 모든 피크를 함유한다.
추가적으로 이들은, 용매, 또한 본 발명의 목적인 목적 화합물의 입체이성질체, 및/또는 불순물의 피크의 신호를 전형적인 1H-NMR 출력물과 같이 나타낼 수 있다.
용매 및/또는 물의 델타-범위 내의 화합물 신호를 나타내기 위해, 용매의 통상적인 피크, 예를 들어 DMSO-D6 중 DMSO의 피크 및 물의 피크가 본 발명자들의 1H-NMR 피크 목록에 제시되며, 통상적으로 평균적으로 높은 강도를 갖는다.
목적 화합물의 입체이성질체의 피크 및/또는 불순물의 피크는 통상적으로 목적 화합물 (예를 들어 >90%의 순도를 가짐)의 피크보다 평균적으로 더 낮은 강도를 갖는다.
이러한 입체이성질체 및/또는 불순물은 특정 제조 방법에 전형적일 수 있다. 따라서 이들의 피크는 "부산물-지문"을 통해 본 발명자들의 제조 방법의 재현을 인식하는 데 도움이 될 수 있다.
공지된 방법 (MestreC, ACD-시뮬레이션, 또한 실험적으로 평가된 예상치 포함)으로 목적 화합물의 피크를 계산하는 전문가는 필요에 따라 임의로 추가의 강도 필터를 사용하여 목적 화합물의 피크를 단리할 수 있다. 상기 단리는 전형적인 1H-NMR 해석에서의 관련 피크 선별과 유사할 것이다.
피크 목록의 NMR-데이터 설명의 추가의 세부사항은 간행물 ["Citation of NMR Peaklist Data within Patent Applications" of the Research Disclosure Database Number 564025]에서 찾아볼 수 있다.
표 A: NMR 피크 목록
생물학적 데이터
실시예 A: 크산토모나스 캄페스트리스 병원체변종 캄페스트리스 시험관내 세포 시험
용매: DMSO
배양 배지: LB 브로쓰 배지 (루리아 브로쓰 밀러(Luria Broth Miller)) 시그마(Sigma)
접종물: 박테리아 현탁액
시험 화합물을 DMSO 중에 가용화시키고, 이러한 용액을 사용하여 요구 범위의 농도를 제조하였다. 검정에 사용된 DMSO의 최종 농도는 ≤ 1%였다.
액체 배지에서 성장시킨 박테리아의 예비-배양물로부터 접종물을 제조하고, 목적하는 광학 밀도 (OD)로 희석하였다.
화합물을 액체 배양 검정에서 박테리아 성장을 억제하는 그의 능력에 대해 평가하였다. 화합물을 박테리아 현탁액을 함유하는 배양 배지에 목적하는 농도로 첨가하였다. 24시간의 인큐베이션 후에, 박테리아 성장의 분광측정 측정에 의해 화합물의 효능을 결정하였다. 화합물을 함유하는 웰에서의 흡광도 값을 화합물이 없는 대조군 웰에서의 흡광도와 비교함으로써 억제를 결정하였다.
본 시험에서, 본 발명에 따른 하기 화합물은 20 ppm의 농도의 시험 화합물에서 직접 활성을 나타내지 않았다: III.01; III.02; III.03; III.04; III.05.
실시예 B: 크산토모나스 캄페스트리스 병원체변종 캄페스트리스 (양배추의 검은썩음병)의 생체내 예방 시험
시험 화합물을 아세톤/디메틸 술폭시드/트윈®의 혼합물 중에서 균질화에 의해 제조한 다음, 물로 희석하여 목적하는 농도를 수득하였다.
양배추의 어린 식물을 상기 기재된 바와 같이 제조된 화합물을 분무함으로써 처리하였다. 대조군 식물은 아세톤/디메틸 술폭시드/트윈®의 수용액만으로 처리하였다.
72시간 후에, 잎에 크산토모나스 캄페스트리스 병원체변종 캄페스트리스의 수성 박테리아 현탁액을 분무함으로써 식물을 오염시켰다. 오염된 양배추 식물을 95% 상대 습도에서 27℃에서 8 또는 10일 동안 인큐베이션하였다.
시험을 접종 8 또는 10일 후에 평가하였다. 0%는 대조군 식물의 효능에 상응하는 효능을 의미하며, 100%의 효능은 질병이 관찰되지 않았음을 의미한다.
본 시험에서, 본 발명에 따른 하기 화합물은 31 ppm의 농도의 시험 화합물에서 적어도 60%의 효능*을 나타냈다: III.01; III.03; III.04; III.08; III.09.
본 시험에서, 본 발명에 따른 하기 화합물은 125 ppm의 농도의 시험 화합물에서 적어도 60%의 효능*을 나타냈다: III.01; III.04; III.05; III.06; III.08; III.09.
*여러 시험의 산술 평균
실시예 C: 비교 실시예
화합물 CMP5를 실시예 B에 기재된 것과 동일한 조건에서 크산토모나스 캄페스트리스 병원체변종 캄페스트리스 (양배추의 검은썩음병)에 대해 생체내 예방 시험에서 시험하였다.
화합물 CMP5를 WO 2004/062361의 교시에 따라 제조하였다.
결과를 하기 표에 나타낸다.
*4회 시험의 산술 평균
본 발명의 화학식 (III)의 화합물은 31 ppm 또는 125 ppm의 농도에서 시험하였을 때 구조적으로 관련된 화합물 CMP5보다 더 우수한 효능을 나타내는 것으로 밝혀졌다.
보다 구체적으로, 화합물 III.01, III.03, III.04, III.08 및 III.09는 31 ppm의 농도에서 적어도 60%의 효능을 나타내는 것으로 나타난 반면, CMP5는 동일한 농도에서 40% 미만의 효능을 나타내는 것으로 나타났다.
화합물 III.01, III.04, III.05, III.06, III.08 및 III.09는 125 ppm의 농도에서 적어도 60%의 효능을 나타내는 것으로 나타난 반면, CMP5는 동일한 농도에서 40% 미만의 효능을 나타내는 것으로 나타났다.
Claims (15)
- 제1항에 있어서, R3이 플루오린 원자, 염소 원자 또는 메틸인 화학식 (III)의 화합물.
- 제1항에 있어서, R3이 R1 및 R2와 상이한 것인 화학식 (III)의 화합물.
- 제1항 내지 제3항 중 어느 한 항에 따른 화학식 (III)의 적어도 1종의 화합물 및 적어도 1종의 농업상 적합한 보조제를 포함하는 조성물.
- 제1항 내지 제3항 중 어느 한 항에 따른 화학식 (III)의 적어도 1종의 화합물 또는 제4항에 따른 조성물을 식물, 식물 부분, 종자, 과실 또는 식물이 성장하는 토양에 적용하는 단계를 포함하는, 박테리아성 질병을 방제하는 방법.
- 제6항에 있어서,
(a) 하기 화학식 (XXII)의 화합물을 하기 화학식 (XXIII)의 화합물 또는 그의 염과 반응시켜 R4가 수소 원자인 제6항에 언급된 바와 같은 화학식 (XXI)의 화합물을 제공하는 단계:
여기서
R1, R2 및 R3은 제1항 내지 제3항 중 어느 한 항에 언급된 바와 같고;
R4는 수소 원자 또는 C1-C6-알킬이고;
U1은 할로겐 원자, 히드록시 기 또는 C1-C6-알콕시 기임;
(b) R4가 C1-C6-알킬인 단계 (a)에서 수득된 화합물의 가수분해를 수행하여 제6항에 언급된 바와 같은 화학식 (XXI)의 화합물을 제공하는 단계
를 포함하는 방법. - 제6항에 있어서,
(a) 하기 화학식 (XXIV)의 화합물의 디아조화에 이어서 방향족 치환을 수행하여 R4가 수소 원자인 제6항에 언급된 바와 같은 화학식 (XXI)의 화합물을 제공하는 단계:
여기서
R1, R2 및 R3은 제1항 내지 제3항 중 어느 한 항에 언급된 바와 같고;
R4는 수소 원자 또는 C1-C6-알킬이고;
U19는 아미노 기, 염소 원자 또는 브로민 원자이고, U20은 아미노 기, 염소 원자 또는 브로민 원자이고;
단 U19 또는 U19 중 적어도 1개는 아미노 기임;
(b) R4가 C1-C6-알킬인 단계 (a)에서 수득된 화합물의 가수분해를 수행하여 제6항에 언급된 바와 같은 화학식 (XXI)의 화합물을 제공하는 단계
를 포함하는 방법. - 하기 화학식 (XXIIa)의 화합물.
여기서
R1 및 R2는 동일하고 브로민 원자 또는 염소 원자이고;
R3은 플루오린 원자, 염소 원자, 브로민 원자, 아이오딘 원자 또는 메틸이고;
U1a는 히드록시 기 또는 C1-C6-알콕시 기이고;
단 R1 및 R2가 염소 원자인 경우에 R3은 염소 원자가 아니고;
단 화학식 (XXIIa)의 화합물은 하기를 나타내지 않는다:
- 메틸 4,5-디클로로-3-플루오로티오펜-2-카르복실레이트 [2166596-88-7],
- 4,5-디클로로-3-플루오로티오펜-2-카르복실산 [2166596-87-6],
- 에틸 4,5-디브로모-3-플루오로티오펜-2-카르복실레이트 [2260624-98-2],
- 4,5-디브로모-3-플루오로티오펜-2-카르복실산 [1628447-64-2],
- 메틸 4,5-디브로모-3-클로로티오펜-2-카르복실레이트 [1501789-47-4],
- 4,5-디브로모-3-아이오도티오펜-2-카르복실산 [854626-46-3],
- 4,5-디브로모-3-클로로티오펜-2-카르복실산 [503308-99-4],
- 에틸 4,5-디브로모-3-클로로티오펜-2-카르복실레이트 [503308-98-3],
- 메틸 4,5-디브로모-3-플루오로티오펜-2-카르복실레이트 [395664-58-1],
- tert-부틸 3,4,5-트리브로모티오펜-2-카르복실레이트 [62224-27-5],
- 에틸 3,4,5-트리브로모티오펜-2-카르복실레이트 [54113-44-9],
- 3,4,5-트리브로모티오펜-2-카르복실산 [53317-05-8],
- 메틸 3,4,5-트리브로모티오펜-2-카르복실레이트 [24647-80-1],
- 에틸 4,5-디브로모-3-메틸티오펜-2-카르복실레이트 [2088257-63-8],
- 4,5-디클로로-3-메틸티오펜-2-카르복실산 [854626-34-9],
- 4,5-디브로모-3-메틸티오펜-2-카르복실산 [854626-32-7],
- 메틸 4,5-디클로로-3-메틸티오펜-2-카르복실레이트 [854626-27-0], 및
- 메틸 4,5-디브로모-3-메틸티오펜-2-카르복실레이트 [648412-53-7].
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