CN102731490A - 作为杀真菌剂的取代异*唑 - Google Patents
作为杀真菌剂的取代异*唑 Download PDFInfo
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- CN102731490A CN102731490A CN2012100986613A CN201210098661A CN102731490A CN 102731490 A CN102731490 A CN 102731490A CN 2012100986613 A CN2012100986613 A CN 2012100986613A CN 201210098661 A CN201210098661 A CN 201210098661A CN 102731490 A CN102731490 A CN 102731490A
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- Prior art keywords
- compound
- phenyl
- pyridyl
- chloro
- alkyl
- Prior art date
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N43/80—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 1,2
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/10—Antimycotics
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- C07D419/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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Abstract
本发明涉及作为杀真菌剂的取代异唑。本发明提供式I化合物:
Description
相关申请
本申请要求于2004年9月10日申请的美国专利临时申请第60/608,589号的权益,该申请内容整体在此引作参考。
技术领域
背景技术
对于植物、动物和人类来说,严重的真菌感染(局部或***性的)发生率一直在持续增加。很多真菌在环境中很常见,但对植物或哺乳动物无害。然而,某些真菌可使植物、人类和/或动物产生疾病。
杀真菌剂为天然或人工合成来源的化合物,其起着保护植物免受真菌(包括卵菌纲(Oomycetes))引起的伤害的作用。当前的农业方法严重依赖杀真菌剂的应用。事实上,某些作物不使用杀真菌剂就不能有效生长。使用杀真菌剂使得栽培者提高作物产量,从而提高该作物的价值。业已开发了大量杀真菌剂。然而,治疗真菌侵染和感染一直是个大问题。此外,杀真菌剂和抗真菌药抗性业已成为严重问题,这使得这些作用剂对某些农业应用和治疗应用无效。如此,仍需要开发新型杀真菌和抗真菌化合物(例如,参见美国专利第6,673,827号;也参见Walter的美国专利第6,617,330号,其阐述作为杀真菌剂的嘧啶-4-烯胺)。
R.Anderson等的美国专利第5,627,137号阐述了作为除草剂的吖嗪基稻瘟肽(azinylphthalide)和相关化合物的制备。
R.Friary等的美国专利第5,679,692号阐述了作为抗组胺药和血小板活化因子拮抗剂的吡啶基羰基哌啶-4-甲醇和类似物的制备。
发明内容
本发明一方面为式I化合物或其盐:
其中:
R1为烷基;烷氧基烷基;卤代烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳基;或任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的杂芳基;
R2为烷基;烷氧基烷基;卤代烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的杂芳基,尤其是2-吡啶基、3-吡啶基或4-吡啶基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的5-嘧啶基;或任选被卤素、烷基、烯基、炔基、烷氧基、烷硫基、卤代烷基、氰基或硝基取代的2-噻唑基或5-噻唑基;
R3为H;烷基;烷氧基烷基;卤代烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳氧基烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳硫基烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的芳基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的杂芳基;或烷基甲硅烷基。
R4为H;酰基(例如乙酰基、苯甲酰基、苯乙酰基);卤代酰基;烷氧羰基;芳氧基羰基;烷基氨基羰基;或二烷基氨基羰基。
本发明化合物和组合物可用作作物保护剂,以抗击或防止真菌侵染,或防治对作物有害的其他病虫害,例如杂草、昆虫或螨类。
本发明第二方面为用于防治和预防植物病原微生物的组合物,其包含联合的本文所述的活性化合物或化合物组合与合适载体。
本发明第三方面为防治或预防病原微生物侵染栽培植物的方法,其包括将本文所述活性化合物或化合物组合以有效防治所述微生物的量施用于所述植物、其部分或其所在地。
本发明另一方面为防治或预防病原微生物侵染工业材料的方法,其包括将本文所述活性化合物以有效防治所述微生物的量施用于所述工业材料、其部分或其所在地。
本发明另一方面为在需治疗对象体内治疗真菌感染的方法,其包括将本文所述活性化合物以有效治疗所述真菌感染的量给予所述对象。
本发明又一方面为本文所述活性化合物用于制备实食本文所述方法(例如本文所述的农业处理、本文所述的工业材料处理、本文所述的对象体内真菌感染的治疗)的组合物(例如农业制剂、药物制剂)的用途。
本发明的前述和其他目标和方面在下面详述。
具体实施方式
本文所用“烷基”是指饱和烃自由基,其可为直链或支链(例如乙基、异丙基、叔戊基或2,5-二甲己基)或环状(例如环丁基、环丙基或环戊基),含有1-24个碳原子。当该术语单独使用和当其作为复合术语的一部分使用(例如“卤代烷基”和相似术语)时,这两种情况都适用该定义。在某些实施方案中,优选的烷基为含有1-4个碳原子的烷基,也称为“低级烷基”。在某些实施方案中,优选的烷基为含有5或6到24个碳原子的烷基,也可称为“高级烷基”。
本文所用“烯基”是指含有2-24个碳的直链或支链烃,其含有至少一个通过除去2个氢而形成的碳-碳双键。代表性“烯基”实例包括但不限于乙烯基、2-丙烯基、2-甲基-2-丙烯基、3-丁烯基、4-戊烯基、5-己烯基、2-庚烯基、2-甲基-1-庚烯基、3-癸烯基等等。本文所用“低级烯基”为烯基子集,是指含有1-4个碳原子的直链或支链烃基。
本文所用“炔基”是指含有2-24个碳原子并含有至少一个碳-碳三键的直链或支链烃基。代表性炔基实例包括但不限于乙炔基、1-丙炔基、2-丙炔基、3-丁炔基、2-戊炔基、1-丁炔基等等。本文所用“低级炔基”为烷基子集,是指含有1-4个碳原子的直链或支链烃基。
“烷氧基”是指上文所述烷基,其也具有能共价连接另一烃基的氧取代基(例如甲氧基、乙氧基和叔丁氧基)。
本文所用“烷硫基”是指通过本文所定义的硫代部分附加到母体分子部分的本文所定义的烷基。代表性烷硫基实例包括但不限于甲硫基、乙硫基代、叔丁硫基、己硫基等等。
“芳基”或“芳香环部分”是指可为单环或多环的芳香取代基,所述多环稠合在一起、共价连接或连接于共同的基团,例如亚乙基部分或亚甲基部分。芳香环可各自含有杂原子,因此“芳基”包括本文所用“杂芳基”。代表性芳基实例包括薁基、茚满基、茚基、萘基、苯基、四氢萘基、联苯基、二苯基甲基、2,2-二苯基-1-乙基、噻吩基、吡啶基和喹啉基。除非另外指出,否则“芳基”意即取代或未取代的芳基,因此芳基部分可任选被卤素原子或其他基团例如硝基、羧基、烷氧基、苯氧基等等取代。另外,芳基可在芳基的任意位置连接到其他部分,这些位点在其它情况下可由氢原子占据(例如2-吡啶基、3-吡啶基和4-吡啶基)。
“杂芳基”意即环状芳香烃,其中一个或多个碳原子为杂原子所取代。若该杂芳基含有超过一个杂原子,则杂原子可相同或不同。杂芳基实例包括吡啶基、嘧啶基、咪唑基、噻吩基、呋喃基、吡嗪基、吡咯基、吡喃基、异苯并呋喃基、色烯基、呫吨基、吲哚基、异吲哚基、吲嗪基、***基、哒嗪基、吲唑基、嘌呤基、喹嗪基、异喹啉基、喹啉基、2,3-二氮杂萘基、1,5-二氮杂萘基、喹喔啉基、异噻唑基和苯并[b]噻吩基。优选的杂芳基为5和6元环,含有独立选自O、N和S的1-3个杂原子。包括每一个杂原子在内的杂芳基可未被取代,或若化学上可行,则被1-4个取代基取代。举例而言,杂原子S可用1或2个氧代基(其可表示为=O)取代。
“农业上可接受盐”意即这样一种盐,其阳离子在形成用于农业或园艺用途的盐的领域为已知并被接受。优选该等盐溶于水。
本文所用“氰基”是指-CN基。
本文所用“卤代”或“卤素”是指-Cl、-Br、-I或-F。
本文所用“卤代烷基”是指至少一个如本文所定义的卤素通过如本文所定义的烷基附加到母体分子部分。代表性卤代烷基实例包括但不限于氯甲基、2-氟乙基、三氟甲基、五氟乙基、2-氯-3-氟戊基等等。
本文所用“羟基”是指-OH基团。
本文所用“硝基”是指-NO2基团。
本文所用“氧基”是指-O-部分。
本文所用“硫代或硫基”是指-S-部分。
本文所用“有机碱”包括但不限于三乙胺、三异丁胺、三异辛胺、三异癸胺、二乙醇胺、三乙醇胺、吡啶、吗啉和其混合物。优选的有机碱种类为有机胺类。
本文所用“无机碱”包括但不限于碳酸钠、碳酸氢钠、碳酸钾和其混合物。
本文所用“惰性溶剂”包括任何合适的惰性溶剂,例如四氢呋喃、N-甲基吡咯烷酮、二甲基甲酰胺、甲苯、二甲醚、甲基·叔丁基醚和二烷、二氯甲烷、氯仿、1,2-二氯乙烷和其混合物。
本文所用“质子溶剂”可为任何合适的质子溶剂,包括但不限于甲醇、乙醇、异丙醇、正丁醇、乙二醇、甲基溶纤剂、乙基溶纤剂、环己醇、丙三醇、二乙二醇、三乙醇胺、聚乙二醇、仲丁醇、正丙醇和叔丁醇。
本文所引用的所有美国专利参考文献的内容在此如同全文叙述一样以其整体内容引作参考。
2.化合物 本发明化合物由结构式I来表示:
其中:
R1为烷基;烷氧基烷基;卤代烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳基;或任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的杂芳基;
R2为烷基;烷氧基烷基;卤代烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的杂芳基,尤其是2-吡啶基、3-吡啶基或4-吡啶基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的5-嘧啶基;或任选被卤素、烷基、烯基、炔基、烷氧基、烷硫基、卤代烷基、氰基或硝基取代的2-噻唑基或5-噻唑基;
R3为H;烷基;烷氧基烷基;卤代烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳氧基烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳硫基烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的芳基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的杂芳基;或烷基甲硅烷基。
R4为H;酰基(例如乙酰基、苯甲酰基、苯乙酰基);卤代酰基;烷氧羰基;芳氧基羰基;烷基氨基羰基;或二烷基氨基羰基。
制备方法 通式结构I(其中R4=H)的组合物可通过亚氨酰氯(carboximidoyl chloride)II与乙炔型甲醇(acetylenic carbinol)III的[3+2]-环加成反应来制备:
该反应在存于惰性溶剂例如DCE(1,2-二氯乙烷)中的有机碱例如三乙胺或存于质子溶剂例如异丙醇中的无机碱例如碳酸氢钠存在下进行。反应时间和温度并不关键,但可在20-60℃温度范围内进行1-24小时。
亚氨酰氯II用氯化试剂例如N-氯代琥珀酰亚胺或次氯酸钠(漂白剂)从相应的肟制备,或从商业来源得到。
通过将有机金属乙炔IV(M=Li,MgX;X=Cl、Br)加入到醛R2CHO(V)中来得到乙炔型甲基III,如下所示:
在某些情况下,当使用乙炔型甲醇III的相应酮(VI)时,[3+2]-环加成进行得更快,收率更高:
在某些情况下,在[3+2]-环加成中与I一起形成I的区域异构体。该区域异构体VIII在生物评估中活性通常不如I。
可用例如存于惰性溶剂例如DMSO(二甲亚砜)中的IBX(邻亚碘酰苯甲酸),在任何合适的时间和温度(例如20℃1-2小时)下,通过氧化从III制备炔酮VI。用存于醇类溶剂(例如乙醇)中的硼氢化钠在0℃将异唑VII还原0.3-2小时,生成异唑I(R4=H)。
用标准酰化或氨基甲酰化条件从I(R4=H)制备异唑,其中R4≠H。举例而言,通过与存于醚溶剂中的乙酸酐和吡啶在室温下过夜反应,从醇I(R=H)合成I的乙酸衍生物(R4=COCH3)。可在存于惰性溶剂(例如***、二氯甲烷)中的有机碱存在下用酸酐(例如乙酸酐、丙酸酐)或酰基氯(例如苯甲酰氯)实施酰化。通过用强碱例如氢化钠接着用存于惰性溶剂例如DMF(二甲基甲酰胺)中的氨基甲酰氯(例如N,N-二甲氨基甲酰氯)处理醇I可实现氨基甲酰化。
例示性化合物。对于防治真菌病原体尤其有用的本发明化合物为这样的化合物,其中:
R1=烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的芳烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的芳基;或任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的杂芳基,
R2=任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的杂芳基,尤其是2-吡啶基、3-吡啶基或4-吡啶基;或任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基或硝基取代的5-嘧啶基;
R3=烷基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的芳基;任选被卤素、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、卤代烷氧基、氰基、硝基取代的杂芳基;或烷基甲硅烷基;和
R4=H。
本发明化合物实例包括但不限于下列:
盐 可以其盐形式得到本文所述化合物和任选所有其异构体。因为某些化合物I具有碱性中心,其可例如形成酸加成盐。举例而言,所述酸加成盐用下列酸形成:无机酸,通常为硫酸、磷酸或卤化氢;有机羧酸,通常为乙酸、草酸、丙二酸、马来酸、反丁烯二酸或邻苯二甲酸;羟基羧酸,通常为抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸;或苯甲酸或有机磺酸,通常为甲磺酸或对甲苯磺酸。具有至少一个酸性基团的式I化合物也可与碱一起形成盐。举例而言,与碱形成的合适盐为金属盐,通常为碱金属盐或碱土金属盐,例如钠盐、钾盐或镁盐,或与氨或有机胺(例如吗啉、哌啶、吡咯烷、单烷基胺、二烷基胺或三烷基胺,通常为乙胺、二乙胺、三乙胺或二甲基丙胺或单羟基烷基胺、二羟基烷基胺或三羟基烷基胺,通常为单乙醇胺、二乙醇胺或三乙醇胺)形成的盐。若合适也可能形成相应的内盐。在本发明范围内,优选农业化学可接受盐或药物上可接受盐。
3.农业化学组合物和用途 本发明活性化合物可用于制备农业化学组合物,用于以与其他抗真菌化合物相似的方式防治真菌。参见例如美国专利第6,617,330号;也参见美国专利第6,616,952号;第6,569,875号;第6,541,500号和第6,506,794号。
本文所述活性化合物可用于保护植物抵抗真菌引起的疾病。为本文目的,应将卵菌纲当作真菌。活性化合物可作为防治植物病虫害的活性组分用于农业部门和相关领域。可将活性化合物用于抑制或消灭出现在有用植物不同季的植物或植物部分(果实、花、叶、茎、块茎、根)上的病虫害,任选同时也保护所述植物后来生长的部分免受例如植物病原微生物侵害。
活性化合物可作为拌种剂(dressing agent)用于处理植物繁殖材料,尤其是种子(果实、块茎、谷粒)和植物插条(例如水稻),以保护抵抗真菌感染以及土壤中存在的植物病原真菌。
举例而言,所述活性化合物可用于抵抗下列种类的植物病原真菌:半知菌类(Fungi imperfecti)(例如葡萄孢属(Botrytis)、Pyricularia、长蠕孢属(Heiminthosporium)、镰孢属(Fusarium)、壳针孢属(Septoria)、尾孢属(Cercospora)和链格孢属(Alternaria))和担子纲(Basidiomycetes)(例如丝核菌属(Rhizoctonia)、驼孢锈菌属(Hemileia)、柄锈菌属(Puccinia))。另外,也可将他们用来抵抗子囊菌纲(Ascomycetes)(例如黑星菌属(Venturia)和白粉菌属(Erysiphe)、叉丝单囊壳属(Podosphaera)、链核盘菌属(Monilinia)、钩丝壳属(Uncinula))和卵菌纲(Oomycetes)(例如疫霉属(Phytophthora)、腐霉属(Pythium)、单轴霉属(Plasmopara))。可治疗的真菌具体实例包括但不限于小麦壳针孢(Septoria tritici)、Stagonospora nodorum、致病疫霉(Phytophthorainfestans)、灰葡萄孢(Botrytis cinerea)、Sclerotinia homoeocarpa和隐匿柄锈菌(Puccinia recondita)。
用本发明活性化合物和组合物保护的目标作物通常包括下列植物种类:谷类(小麦、大麦、黑麦、燕麦、水稻、玉米、高梁和有关物种);甜菜(糖用甜菜和饲料甜菜);梨果、核果和浆果(苹果、梨、李、桃、杏、樱桃、草莓、悬钩子和黑莓);豆科植物(菜豆、小扁豆、豌豆、大豆);油料植物(油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生);黄瓜类植物(南瓜、黄瓜、甜瓜);纤维植物(棉花、亚麻、***、黄麻);柑橘类水果(橙子、柠檬、葡萄柚、柑桔);蔬菜(菠菜、莴苣、芦笋、甘蓝、胡罗卜、洋葱、西红柿、马铃薯、红辣椒);樟科(鳄梨、肉桂、樟脑)或诸如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、包括葡萄、忽布、香蕉、草根在内的蔓生植物和天然橡胶植物以及观赏植物(花卉、灌木、阔叶树和常绿植物,例如松柏类植物)等植物。该清单并不表示任何限制。
活性化合物可以组合物形式使用,可与另外的化合物同时或序贯施用于待处理的作物区域或植物。这些另外的化合物可为例如肥料或微量营养素供体或其他影响植物生长的制剂。它们也可为选择性除草剂以及杀虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂、植物生长调节剂、植物催化剂或这些制剂中的几种的混合物,若需要其可与另外的载体、表面活性剂或制剂领域常规采用的有助于施用的助剂一起。
可将活性化合物与其他杀真菌剂混合,某些情况下产生意想不到的协同活性。
特别优选的混合成分为下列:唑类,例如戊环唑、双苯***醇、丙环唑、醚唑、烯唑醇、环唑醇、氧唑菌(epoxiconazole)、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、抑霉唑、酰胺唑、环戊唑醇、戊唑醇、氟醚唑、腈苯唑、环戊唑菌、腈菌唑、perfurazoate、戊菌唑、糠菌唑、啶斑肟、咪鲜安、***酮、唑菌醇、氟菌唑或戊叉唑菌;嘧啶基甲醇类,例如嘧啶醇、异嘧菌醇或氟苯嘧啶醇;2-氨基-嘧啶,例如磺嘧菌灵、甲菌定或乙菌定;吗啉类,例如吗菌灵、苯锈啶、丁苯吗啉、螺茂胺或克啉菌;苯胺嘧啶类,例如环丙嘧啶、二甲嘧菌胺或嘧菌胺;吡咯类,例如拌种咯或氟菌;苯酰胺类,例如苯霜灵、呋霜灵、甲霜灵、R-甲霜灵、呋酰胺或恶霜灵;苯并咪唑类,例如苯菌灵、多菌灵、咪菌威、麦穗宁或噻菌灵;二甲酰亚胺类,例如乙菌利、菌核利、异丙定(iprodine)、甲菌利、腐霉利或乙烯菌核利;甲酰胺类,例如萎锈灵、甲呋酰苯胺、氟酰胺、灭锈胺、氧化萎锈灵或溴氟唑菌;胍类,例如双辛胍、十二烷胍或双胍辛;亚胺菌类(strobilurines),例如腈嘧菌酯、亚胺菌、叉胺苯酰胺、唑菌胺酯、啶氧菌酯、SSF-129、2[(2-三氟甲基)-吡啶-6-基氧基甲基]-3-甲氧基-丙烯酸甲酯或2-[{α[(α-甲基-3-三氟甲基-苯甲基)亚氨基]-氧基}-邻甲苯基]-乙醛酸-甲酯-O-甲基肟(肟菌酯);二硫代氨基甲酸酯类,例如福美铁、代森锰锌、代森锰、代森联、丙森锌、福美双、代森锌或福美锌;N-卤代甲硫基-二甲酰亚胺类,例如敌菌丹、克菌丹、抑菌灵、氟氯菌核利、灭菌丹或甲苯氟磺胺;铜化合物,例如波尔多液、氢氧化铜、氧氯化铜、硫酸铜、氧化亚铜、代森锰铜或喹啉铜;硝基苯酚衍生物类,例如敌螨普或异丙清;有机磷衍生物类,例如克瘟散、异稻瘟净、稻瘟灵、氯瘟磷、定菌磷或甲基立枯磷;和其他具有不同结构的化合物,例如苯并噻二唑、过敏致病性蛋白、敌菌灵、灭瘟素、灭螨猛、地茂散、百菌清、清菌脲、二氯萘醌、哒菌酮、氯硝胺、乙霉威、烯酰吗啉、二噻农、土菌灵、唑菌酮、咪唑菌酮、三苯锡、嘧菌腙、氟啶胺、磺菌胺、菌剂嘧、乙膦铝、恶霉灵、春雷霉素、磺菌威、戊菌隆、稻瘟肽、多抗霉素、烯丙苯噻唑、霜霉威、咯喹酮、喹氧灵、五氯硝基苯、硫磺粉、咪唑嗪、三环唑、嗪胺灵、有效霉素、(S)-5-甲基-2-甲硫基-5-苯基-3-苯基氨基-3,5-二氢咪唑-4-酮(RPA 407213)、3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧丙基)-4-甲基苯甲酰胺(RH-7281)、N-烯丙基-4,5-二甲基-2-三甲基甲硅烷基噻吩-3-甲酰胺(MON 65500)、4-氯-4-氰基-N,N-二甲基-5-对甲苯基咪唑-1-磺酰胺(IKF-916)、N-(1-氰基-1,2-二甲基丙基)-2-(2,4-二氯苯氧基)-丙酰胺(AC 382042)或丙森锌(SZX 722)。
活性化合物可单独或和以上杀真菌剂组合与一种或多种***获得性抗性诱导剂(″SAR″诱导剂)混合。已知SAR诱导剂并阐述于例如美国专利第6,919,298号中。一般而言,SAR诱导剂为具有启动植物对致病剂(包扩但不限于病毒、细菌、真菌或这些因素组合)的抗性能力的任何化合物。另外,SAR诱导剂可诱导植物抗昆虫取食,其如Enyedi等(1992;Cell 70:879-886)所述。例示性SAR诱导剂包括多种化合物结构家族,但因其诱导对植物疾病和/或害虫取食抗性的能力而联合在一起。一类SAR诱导剂为水杨酸盐。商用SAR诱导剂苯并噻二唑(可作为自Syngenta得到)、过敏致病性蛋白(可作为MessengerTM自Eden Biosciences得到)、来自酿酒酵母(Saccharomycescerevisiae)的酵母膏水解物(可作为自MorseEnterprises Limited,Inc.of Miami,Florida得到)、烯丙苯噻唑可用于本发明。包括Goemar的产品在内的激卫素为另一类也可使用的SAR诱导剂。另外,在该方面乙烯、其生物合成前体或释放乙烯的化合物例如乙烯利被认为是有用的SAR诱导剂。也参见美国专利第6,919,298号。
合适的载体和助剂可为固态或液态,其为用于制剂技术的物质,例如天然或再生矿物质、溶剂、分散剂、润湿剂、胶粘剂、增稠剂、粘合剂或肥料。
施用本发明活性化合物或含有至少一种所述化合物的农业化学组合物的优选方法为叶敷。施用频率和比率将视相应病原体侵染的风险而定。然而,活性化合物也可通过用液态制剂湿透植物所在地而经由土壤穿过根部渗透植物(***性作用),或通过将该化合物以固态形式(例如以粒状形态)施用到土壤(土壤施用)。在需水作物例如水稻中,可将此等颗粒状物施用到淹灌的稻田里。也可通过用杀真菌剂的液态制剂浸渍种子或块茎,或用固态制剂包裹种子或块茎,来将活性化合物施用于种子(包裹)。
本文所用术语所在地意欲包括待处理的作物生长所在田地,或栽培植物种子播种所在田地,或将被放置到土壤中的种子所在地。术语种子意欲包含植物繁殖材料,例如插条、幼苗、种子、发芽的种子或浸泡的种子。
活性化合物以未修饰的形式使用,或优选与制剂领域常规使用的助剂一起使用。为此,其以已知方式方便地调配为可乳化浓缩液、可涂覆糊状物、可直接喷雾或稀溶液、稀乳状液、可湿性粉剂、可溶性粉剂、撒(喷)粉、粒剂,也可用例如聚合物质包封。正如所述类型的组合物一样,按照计划目的和主要环境选择施用方法,例如喷雾、雾化、喷粉、撒布、包衣或倾入。
有利的施用比率通常为每公顷(ha)5g-2kg活性组分(a.i.),优选10g-1kg a.i./ha,最优选20g-600g a.i./ha。当用作种子浸湿剂(seeddrenching agent)时,方便的用量为每kg种子10mg-1g活性物质。
通常通过均匀混合和/或将化合物与补充剂例如溶剂、固态载体和任选表面活性化合物(表面活性剂)碾磨用已知方法来制备所述制剂,即含有式I化合物和必要时含有固态或液态助剂的组合物。
合适的载体和助剂可为固态或液态,相应于制剂技术通常采用的物质,例如天然或再生的矿物质、溶剂、分散剂、润湿剂、胶粘剂、增稠剂、粘合剂或肥料。此等载体例如阐述于WO 97/33890中。
制剂领域通常使用的其他表面活性剂为行家所知,或可在有关文献中找到。
农业化学制剂通常含有0.1-99%重量(优选0.1-95%重量)的式I化合物、99.9-1%重量(优选99.8-5%重量)的固态或液态助剂、0-25%重量(优选0.1-25%重量)的表面活性剂。
然而,优选将商业产品调配为浓缩物,终端使用者通常将使用稀制剂。
所述组合物也可含有其他助剂,例如稳定剂、消沫剂、黏性调节剂、粘合剂或胶粘剂以及肥料、微量营养素供体或为获得特定效果的其他制剂。
4.工业材料 本发明化合物和组合也可用于防治工业材料真菌感染(尤其是由霉菌引起的)领域,包括保护工业材料免受真菌侵袭和在此感染发生后降低或根除工业材料的真菌感染。工业材料包括但不限于有机和无机材料木材、纸张、皮革、天然和合成纤维、其复合材料例如刨花板、胶合板、墙板等等、机织布和非机织布、建筑物表面和材料、冷却和加热***表面和材料、通风和空调***表面和材料等等。可将本发明化合物和组合以有效抑制或预防不利作用(例如腐烂、变色或与上述同样的方式发霉)的量施用于此等材料或表面。利用或混合其中已施用此等化合物或组合的工业材料建造的结构和住所同样受到保护以免受真菌侵袭。
5.药物用途 除了前述情况外,本发明活性化合物还可用于医学和兽医目的、用于治疗人类和动物受治疗者(包括但不限于马、牛、羊、狗、猫等等)的真菌感染。此等感染实例包括但不限于下面的疾病,例如甲真菌病、孢子丝菌病、蹄坏疽病、丛林皮病(jungle rot)、波伊德假霉样真菌(Pseudallescheria boydii)、帚霉属(scopulariopsis)或足癣(有时通称为白色划痕病)以及免疫缺陷患者(例如AIDS患者和移植患者)的真菌感染。因此,真菌感染可为皮肤或角蛋白材料(例如毛发、蹄或指甲)以及全身性感染,例如那些由假丝酵母(Candida spp.)、新型隐球菌(Cryptococcus neoformans)、曲霉(Aspergillus spp.)引起的感染,例如如在肺曲霉病和卡氏肺孢子虫(Pneumocystis carinii)性肺炎中的感染。本文所述活性化合物可与药物上可接受载体联合,以按照(例如)美国专利第6,680,073号;第6,673,842号;第6,664,292号;第6,613,738号;第6,423,519号;第6,413,444号;第6,403,063号;和第6,042,845号(申请者明确提出的内容在此整体引作参考)所述的已知技术有效治疗感染的量给予或施与此等患者或感染(例如局部、胃肠外)。
本文所用“药物上可接受”,是指在合理医疗判断范围内适于与人类和动物的组织接触、没有过多的毒性、刺激、***反应或其他问题或并发症、且具有相称的合理利益/风险比率的那些化合物、材料、组合物和/或剂型。
本文所用“药物上可接受载体”意即涉及将目标肽模拟物药物从机体的一个器官或部份携带或运输到机体的另一器官或部份的药物上可接受的材料、组合物或媒介,例如液态或固态填充剂、稀释剂、赋形剂、溶剂或包胶材料。每一载体与制剂的其他组分相容和对所述患者无害的意义上讲应该为“可接受的”。可用作药物上可接受载体的某些材料实例包括:(1)糖类,例如乳糖、葡萄糖和蔗糖;(2)淀粉,例如玉米淀粉和马铃薯淀粉;(3)纤维素和其衍生物,例如羧甲基纤维素钠、乙基纤维素和乙酸纤维素;(4)粉状黄蓍胶;(5)麦芽;(6)明胶;(7)滑石粉;(8)赋形剂,例如可可脂和栓剂用蜡;(9)油类,例如花生油、棉籽油、红花油、芝麻油、橄榄油、玉米油和豆油;(10)二醇类,例如丙二醇;(11)多元醇,例如甘油、山梨醇、甘露醇和聚乙二醇;(12)酯类,例如油酸乙酯和月桂酸乙酯;(13)琼脂;(14)缓冲剂,例如氢氧化镁和氢氧化铝;(15)藻酸;(16)无热原水;(17)等渗盐水;(18)Ringer氏液;(19)乙醇;(20)磷酸盐缓冲液;和(21)在药物制剂中采用的其他无毒相容性物质。
本发明制剂包括那些适于口服给药、经鼻给药、局部给药(包括口腔含化和舌下)、直肠给药、***给药和/或胃肠外给药的制剂。该等制剂可方便地以单位剂型呈现,可通过制药领域熟知的任何方法来制备。可与载体材料联合以形成单剂量形式的活性组分的量将视待治疗的宿主、具体给药方式而变化。可与载体材料联合以形成单剂量形式的活性组分的量通常应为产生治疗效果的活性组分的量。一般而言,以100%计,应在约1%-约99%活性组分范围内,优选约5%-约70%,最优选约10%-约30%。
制备这些制剂或组合物的方法包括使本发明化合物与所述载体和任选的一种或多种辅助组分结合这一步骤。一般而言,通过使本发明的肽或肽模拟物与液态载体或细粉状固态载体或这二者均一和密切结合来制备该等制剂,然后必要时将该产物定型。
除了活性组分外,软膏剂、糊剂、霜剂和凝胶剂可含有赋形剂,例如动物和植物脂肪、油类、蜡、石蜡、淀粉、黄蓍胶、纤维素衍生物、聚乙二醇、硅酮、膨润土、硅酸、滑石粉和氧化锌或其混合物。
除了本发明化合物外,粉剂和喷雾剂可含有赋形剂,例如乳糖、滑石粉、硅酸、氢氧化铝、硅酸钙和聚酰胺粉末或这些物质的混合物。喷雾剂可另外含有常规喷射剂,例如氯氟烃和挥发性未取代烃,例如丁烷和丙烷。
适于口服给药的制剂可以分开单位呈现,例如以下形式:胶囊、扁囊剂、锭剂或片剂,各自含有预定量的活性化合物;粉剂或颗粒剂;溶液剂或水性或非水性液态混悬剂;或水包油或油包水型乳剂。可通过任何合适的制药方法制备此等制剂,包括使所述活性化合物和合适载体(可含有一种或多种上述辅助组分)结合这一步骤。一般而言,通过将所述活性化合物与液态或细粉状固态载体或二者均一和密切混合来制备本发明制剂,然后必要时将得到的混合物定型。举例而言,可通过将含有所述活性化合物和任选一种或多种辅助组分的粉末或颗粒压制或模制来制备片剂。可通过在合适机器中将任选与粘合剂、润滑剂、惰性稀释剂和/或表面活性/分散剂混合的自由流动形式(例如粉末或颗粒)的化合物压制来制备压片。可通过在合适机器中将用惰性液态粘合剂弄湿的粉状化合物模制来制备模制片。
适于胃肠外给药的本发明药物组合物包含一种或多种本发明活性化合物与一种或多种下述药物上可接受物质:无菌等渗水性或非水性溶液、分散液、混悬液或乳状液,或可在临用前重建为注射用溶液或分散液的无菌粉末;它们可含有抗氧化剂、缓冲剂、抑菌剂、为制剂提供与目标受体血液等渗的溶质或助悬剂或增稠剂。
可用于本发明药物组合物的合适水性和非水性载体的实例包括水、乙醇、多元醇(例如丙三醇、丙二醇、聚乙二醇等等)及其合适混合物、植物油(例如橄榄油)和注射用有机酯例如油酸乙酯。举例而言,通过使用包衣材料例如卵磷脂,通过在分散剂情况下保持所需的粒径,以及通过使用表面活性剂,可维持适当的流动性。这些组合物也可含有助剂,例如防腐剂、润湿剂、乳化剂和分散剂。可通过包含各种抗细菌剂和其他抗真菌剂(例如对羟基苯甲酸酯类、三氯叔丁醇、苯酚山梨酸等等)来确保预防微生物的作用。在所述组合物中包括等渗剂(例如糖类、氯化钠等等)也可能是理想的。另外,通过包含延迟吸收的作用剂例如单硬脂酸铝和明胶,可带来延长吸收的注射用药物形式。
当将本发明化合物作为药物给予人类和动物时,可给予其本身,或作为含有例如0.1-99.5%(更优选0.5-90%)活性组分与药物上可接受载体的药物组合物给予。
可以任何合适的给药方式给予本发明制剂,包括口服、胃肠外、局部、透皮、直肠给药等等。当然本发明制剂以适于各个给药途径的形式来给予。举例而言,其以片剂或胶囊剂形式给予,通过注射、吸入、洗眼液(eye lotion)、软膏剂、栓剂等等给予,通过注射、输注或吸入来给予;通过洗剂或软膏剂局部给予;和通过栓剂直肠给予。优选局部给药或胃肠外给药。
本文所用“胃肠外给药”和“胃肠外给予”意即除肠道和局部给药以外的给药方式,通常通过注射给予,包括但不限于静脉内、肌内、动脉内、鞘内、囊内、眼窝内、心脏内、皮内、腹膜内、经气管、皮下、表皮下、关节内、囊下、蛛网膜下、脊柱内和胸骨内的注射和输注。
为了得到对于特定患者、组合物、给药方式而言有效达到所期需治疗反应(例如抗真菌活性)而对患者没有毒性的活性组分的量,本发明药物组合物中活性组分的实际剂量水平可有所变化。所选剂量水平将视多种因素而定,包括所用特定活性化合物的活性、给药途径、给药时间、所用特定活性化合物的***速率、治疗期限、与所用特定抑制剂联合使用的其他药物、化合物和/或材料、待治疗患者的年龄、性别、体重、病况、一般健康状态和既往就医史、医学领域熟知的相似因素。具有本领域一般技术的医生或兽医可易于确定和给出所需药物组合物的有效量。举例而言,医生或兽医开始可让药物组合物中所采用的本发明化合物的剂量低于为达到所期需治疗效果所需要的水平,逐渐增加剂量直至达到所期需效果。总的建议是,约0.01或0.1-约50、100或200mg/kg剂量将具有治疗功效,计算的所有重量依据该活性化合物的重量,包括采用盐的情况。
在下列非限制性实施例中更详细地解释本发明。
实施例1
3-(2,6-二氯苯基)-4-[(3-吡啶基)
和3-(2,6-二氯苯基)-5-[(3-吡啶基)
将存于2mL异丙醇的55mg(0.24mmol)2,6-二氯-N-羟基苯亚氨酰氯(hydroxybenzenecarboximidoyl chloride)、50mg(0.24mmol)1-(3-吡啶基)-3-三甲基甲硅烷基-2-丙炔-1-醇和20mg(0.24mmol)碳酸氢钠混合物于55℃加热24小时。用醚稀释该反应混合物。用饱和氯化钠溶液洗涤***层,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去***。通过制备性薄层层析(prep TLC)来纯化该粗产物,分离出2个产物。极性较弱的产物(10mg,0.025mmol)经鉴定为3-(2,6-二氯苯基)-4-[(3-吡啶基)羟基-甲基]-5-三甲基甲硅烷基异唑。1H NMR(CDCl3):δ0.45(br s,9),5.82(s,1)和7.40ppm(d,1).MS m/z:393.0(M+H)。
极性较强的产物为3-(2,6-二氯苯基)-5-[(3-吡啶基)羟甲基]-4-三甲基甲硅烷基异唑。1H NMR(CDCl3):δ0.20(m,9),6.12(s,1),7.80(d,1)和7.87ppm(d,1).MS m/z:393.0(M+H)。
实施例2
5-(3-氯苯基)-3-(2,4-二氯苯基)-4-
将存于2.5mL异丙醇的53mg(0.24mmol)2,4-二氯-N-羟基苯亚氨酰氯、50mg(0.21mmol)1-(3-吡啶基)-3-(3-氯苯基)-2-丙炔-1-醇、26mg(0.31mmol)碳酸氢钠混合物在装配有热沙浴的台式旋转振荡器上于55℃加热。20小时后,再加入20mg 2,4-二氯-N-羟基苯亚氨酰氯和10mg碳酸氢钠,将该反应混合物搅拌和再加热16小时。然后用***稀释该混合物,用饱和氯化钠洗涤该溶液,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去***。通过prep TLC纯化粗产物,得到15mg(0.035mmol)5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟甲基]异唑。1H NMR(CDCl3):δ5.92(br s,1),7.04(d of d,1),7.12(d,1),7.72(m,1),8.86(br s,1)和8.29ppm(br s,2).MS m/z:430.9(M+H)。
实施例3
向存于2mL吡啶的43mg(0.10mmol)5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟甲基]异唑溶液中加入19μL(0.20mmol)乙酸酐。将该反应物在室温下搅拌过夜,然后真空下除去吡啶。将该残留物溶于乙酸乙酯中,用饱和氯化钠洗涤,经硫酸镁干燥乙酸乙酯部分。过滤除去干燥剂,通过旋转蒸发除去乙酸乙酯。通过制备性薄层层析(prep TLC)纯化粗产物,得到35mg(0.074mmol)5-(3-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)乙酰氧基甲基]异唑。
实施例4
向存于2.5mL二甲亚砜(DMSO)的200mg(1.06mmol)4,4-二甲基-1-吡啶基-2-戊炔-1-醇溶液中加入443mg(1.58mmol)邻亚碘酰苯甲酸(IBX)。将该反应混合物在室温下搅拌过夜,然后过滤除去固体。用***稀释滤液,用饱和氯化钠溶液洗涤。分离有机部分,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去***。酮产物4,4-二甲基-1-(3-吡啶基)-2-戊炔-1-酮(182mg)无需任何纯化就可直接使用。
将存于2.5mL异丙醇的72mg(0.32mmol)2,4-二氯-N-羟基苯亚氨酰氯、60mg(0.32mmol)4,4-二甲基-1-(3-吡啶基)-2-戊炔-1-酮和32mg(0.38mmol,1.2当量)碳酸氢钠混合物于55℃在台式旋转振荡器上加热16小时。第二次加入25mg亚氨酰氯和10mg碳酸氢钠,接着再在55℃加热20小时。冷却该反应混合物,用***稀释,然后用饱和碳酸氢钠洗涤。经硫酸镁干燥***部分。过滤除去干燥剂,通过旋转蒸发除去***。通过prep TLC纯化粗产物,得到92mg油状产物3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羰基]异唑。1H NMR(CDCl3):δ1.47(s,9),7.90(m,1),7.60(br s,1)和8.72ppm(br s,1).MSm/z:375.0(M+H)。
实施例5
3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)
于0℃向存于5mL乙醇的92mg(0.24mmol)3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羰基]异唑溶液中加入20mg(0.53mmol)硼氢化钠。2小时后,将该反应混合物倒入水中,用乙酸乙酯萃取该产物几次。用饱和氯化钠洗涤合并的乙酸乙酯部分,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去乙酸乙酯。通过prepTLC纯化粗产物,得到68mg(0.18mmol)3-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-4-[(3-吡啶基)羟基-甲基]异唑。1H NMR(CDCl3):δ1.52(s,9),6.14(br s,1),6.86(d,1),7.38(m,1),8.27(br s,1)和8.33ppm(m,1).MSm/z:377.0(M+H)。
实施例6
5-(2-氯苯基)-3-(2,4-二氯苯基)
-4-[(3-吡啶基)羟甲基]异唑(化合物14)
在氮气中向存于10mL四氢呋喃(THF)中冷却到-78℃的655mg(4.8mmol)2-氯苯基乙炔溶液加入存于己烷的3.0mL(4.8mmol)1.6M正丁基锂。将该溶液于-78℃搅拌2小时,然后加入存于2.5mL四氢呋喃(THF)的514mg(4.8mmol)3-吡啶甲醛溶液。3.5小时后,将该反应混合物倒入水中。用***萃取该有机产物几次。用饱和碳酸氢钠洗涤合并的***萃取物,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去***,得到油状物3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-醇。
将存于3mL异丙醇的52mg(0.23mmol)2,4-二氯-N-羟基苯亚氨酰氯、50mg(0.21mmol)3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-醇和30mg(0.36mmol)碳酸氢钠混合物于55℃加热振荡过夜。冷却该反应混合物,用***稀释,然后用饱和碳酸氢钠洗涤。经硫酸镁干燥***部分。过滤除去干燥剂,通过旋转蒸发除去***。通过prep TLC纯化粗产物,得到15mg(0.035mmol)5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟甲基]异唑。1H NMR(CDCl3):δ5.80(br s,1).MS m/z:431.0(M+H)。
实施例7
5-(2-氯苯基)-3-(2,4-二氯苯基)
将存于2.5mL异丙醇的56mg(0.25mmol)2,4-二氯-N-羟基苯亚氨酰氯、60mg(0.25mmol)3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-酮和30mg(0.36mmol)碳酸氢钠混合物于55℃加热振荡过夜。然后再加入30mg亚氨酰氯和15mg碳酸氢钠,将该混合物再加热20小时。冷却该反应混合物,用***稀释,然后用饱和碳酸氢钠洗涤。经硫酸镁干燥***部分。过滤除去干燥剂,通过旋转蒸发除去***。通过prep TLC纯化粗产物,得到90mg(0.21mmol)5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羰基]异唑。1H NMR(CDCl3):δ7.16(m,1),7.60(m,2),7.92(m,1),8.53(br d,1)和8.74ppm(br s,1).MS m/z:428.9(M+H)。
于0℃向存于3mL乙醇的80mg(0.19mmol)5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羰基]异唑溶液中加入40mg(1.06mmol)硼氢化钠。将该混合物搅拌2小时,然后用乙酸乙酯稀释。用饱和氯化钠溶液洗涤乙酸乙酯溶液,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去乙酸乙酯。通过prep TLC纯化粗产物,得到65mg(0.15mmol)5-(2-氯苯基)-3-(2,4-二氯苯基)-4-[(3-吡啶基)羟甲基]-异唑。1H NMR(CDCl3):δ5.80(br s,1),6.97(m,1),8.23(br s,1)和8.28ppm(br s,1).MS m/z:431.0(M+H)。
实施例8
5-(2-氯苯基)-3-(2,4-二氯苯甲基)
-4-[(3-吡啶基)羟甲基]异唑(化合物15)
将存于mL二氯甲烷的59mg(0.25mmol)2,4-二氯苯甲基亚氨酰氯(按G.Kumaran和G.H.Kulkarni,J.Org.Chem.1997,62,1516制备)、50mg(0.21mmol)3-(2-氯苯基)-1-(3-吡啶基)-2-丙炔-1-酮、43μL(0.31mmol)三乙胺溶液在密封管制瓶中于55℃加热过夜。冷却该反应混合物,用***稀释,用饱和氯化钠洗涤,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去溶剂。通过prep TLC纯化粗产物,得到50mg(0.11mmol)5-(2-氯苯基)-3-(2,4-二氯苯甲基)-4-[(3-吡啶基)羰基]异唑。1H NMR(CDCl3):δ4.23(s,2),7.48(d,1),7.88(d of d,1),8.66(br d,1)和8.70ppm(br s,1).MS m/z:442.9(M+H)。
于室温下向存于15mL THF的50mg(0.11mmol)5-(2-氯苯基)-3-(2,4-二氯苯甲基)-4-[(3-吡啶基)羰基]异唑溶液中加入21mg(0.56mmol)硼氢化钠。2小时后,用乙酸乙酯稀释该溶液,用饱和氯化钠洗涤,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去溶剂。通过prep TLC纯化粗产物,得到39mg(0.088mmol)5-(2-氯苯基)-3-(2,4-二氯苯甲基)-4-[(3-吡啶基)羟甲基]异唑。1H NMR(CDCl3):δ3.91(d,1),4.00(d,1),6.97(br s,1),7.64(d,1),8.42ppm(brm,2).MS m/z:445.0(M+H)。
实施例9
5-(3-氯苯基)-3-(2-氟-5-三氟甲基苯基)
向存于5mL二甲基甲酰胺(DMF)的643mg(3.10mmol)2-氟-5-三氟甲基苯甲醛肟溶液中加入456mg(3.41mmol)N-氯代琥珀酰亚胺(参见K.-C.Liu,B.R.Shelton和R.K.Howe,J.Org.Chem.1980,45,3916)。将该反应混合物在室温下搅拌过夜,然后用乙酸乙酯稀释。用饱和氯化钠洗涤乙酸乙酯溶液,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去溶剂,得到675mg(2.79mmol)结晶2-氟-5-三氟甲基-N-羟基苯亚氨酰氯,为纯白色。
将存于2.5mL异丙醇的60mg(0.25mmol)2-氟-5-三氟甲基-N-羟基苯亚氨酰氯、50mg(0.21mmol)3-(3-氯苯基)1-(3-吡啶基)-2-丙炔-1-酮(和上述从3-氯苯基乙炔合锂和3-吡啶甲醛接着IBX氧化相似程序制备)和26mg(0.36mmol)碳酸氢钠混合物于55℃加热振摇过夜。再加入30mg亚氨酰氯和15mg碳酸氢钠,将该反应物再加热24小时。冷却该混合物,用***稀释。用饱和氯化钠洗涤***部分,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去溶剂。通过prep TLC纯化残留物,得到56mg(0.13mmol)5-(3-氯苯基)-3-(2-氟-5-三氟甲基苯基)-4-[(3-吡啶基)羰基]异唑。1H NMR(CDCl3):δ7.10(t,1),7.41(m,1),7.52(m,1),8.65(br s,1)和8.86ppm(br s,1).MS m/z:447.0(M+H)。
向存于2mL乙醇的56mg(0.13mmol)5-(3-氯苯基)-3-(2-氟-5-三氟甲基-苯基)-4-[(3-吡啶基)羰基]异唑溶液中加入24mg(0.63mmol)硼氢化钠。于室温2小时后,用乙酸乙酯稀释该反应混合物。用饱和氯化钠洗涤该溶液,经硫酸镁干燥。过滤除去干燥剂,通过旋转蒸发除去溶剂。通过prep TLC纯化残留物,得到44mg(0.098mmol)5-(3-氯苯基)-3-(2-氟-5-三氟甲基苯基)-4-[(3-吡啶基)羟甲基]异唑。1HNMR(CDCl3):δ6.01(s,1),7.01(m,1),7.83(m,1),8.27(m,1)和8.35ppm(br s,1).MS m/z:449.0(M+H)。
实施例10
生物学筛选
用微孔板来测定本发明所述化合物的杀真菌活性。在初步筛选时,将存于1μL二甲亚砜(DMSO)的试验化合物置于96孔微孔板的各孔中。然后将由1.5%琼脂构成的100μL基本培养基加到各孔中,使其冷却。最后,通过加入10μL真菌孢子水性悬浮液到固态琼脂表面来接种。盖上微孔板,置于20℃受控环境中培养。3-5天(随病原体不同而变化)后,通过目测和光度分析真菌生长来确定杀真菌活性。在所有测定中包括了商用标准品(腈嘧菌酯、苯菌灵、克菌丹、百菌清、唑酮菌、氟硅唑、丙环唑)。测试病原体包括小麦壳针孢(Septoria tritici)、Stagonospora nodorum、致病疫霉(Phytophthora infestans)和灰葡萄孢(Botrytis cinerea)。在初步筛选中通过对试验化合物的3倍系列稀释来获得发现能杀真菌的化合物的剂量反应数据。杀真菌活性以μM浓度计的IC50值来表示,本发明涵盖的某些化合物的杀真菌活性包括在下表1中。以百分率表示的方差系数(标准偏差与平均值的比率)示于圆括号中。
IC50(μM):A=0-0.1;B=0.11-1.0;C=1.1-10;D=11-100;E=>100C.V.(%):(a)=0-5;(b)=6-15;(c)=16-30(d)=>30
实施例11
化合物4的草皮试验
春天对15年龄的匍匐剪股颖栽培变种Penncross草皮进行杀真菌剂试验。在美国南部用与维护剪股颖高尔夫草地相似的培育实践来维护草皮。计划分小区(0.5x1.0m)来处理,随机完全区组设计,4次重复。化合物4作为25%活性组分(重量/重量)气动碾磨的(air milled)可湿润粉末来施用。化合物4的施用比率如下(克活性组分/1000平方英尺):2.2、4.4和8.8。所有其他杀真菌剂按照其标注来施用(BannerMAXX 1.3ME和Insignia 20WG)。在施用初始预防性治疗后6小时,草皮用Sclerotinia homoeocarpa(通用名:银元斑(dollar spot))侵染的、经高压灭菌的苇状羊茅种子进行接种。所述小区每天于1700点接受大约0.24英寸灌溉用水,以确保每夜叶片湿润以便进行感染。从初始施用日起大约每隔7天用Horsfall-Barratt等级级别来目测估计疾病严重程度。用0-9级来评估草皮质量,其中0=坏死、稀疏叶幕,而9=深绿色稠密叶幕。对病害和质量值进行方差分析,用Scott-Knott聚类分析程序在统计上分开平均值。
在未治疗的小区中银元斑很严重,达到峰值>50%病害。在研究期间,与未治疗的对照比较,所有治疗组病害受到显著抑制(α≤0.05)。对于剪股颖高尔夫草地而言,平均病害等级<3.0%被认为是可接受的。根据可接受标准,在试验期的大部分时间内只有Banner MAXX和化合物4是提供有效防治的治疗。
与未治疗的对照比较,所有治疗皆显著(α<0.05)改进草皮质量。对于剪股颖高尔夫草地而言,质量等级>6.0被认为是可接受的。最高质量等级与用Banner MAXX或化合物4治疗的小区相关。在任一小区上均未观察到可察觉的植物毒性。草皮质量降低主要是由硬币圆状斑病引起。
实施例12
化合物4的谷类试验
用软质红粒冬小麦栽培变种Sisson进行化合物4的田间试验。非常干燥的天气使得试验晚期叶锈病(隐匿柄锈菌(Puccinia recondita):PUCCRT)自然发生率低。将化合物4作为具有以下配方的9.5%活性组分(重量/重量)可乳化浓缩液施用(每一个都为重量/重量):9.5%化合物4、9.5%m-Pyrol、65%Surfadone LP-100、6%Surfadone LP-300、5%Toximul 3463F和5%Toximul 3464F。化合物4的施用比率如下(克活性组分/公顷:g a.i./ha):140、280和421。化合物4显示出对锈病有很好的防治,统计上与试验中所用的商用标准品[Stratego(91和183ga.i./ha)、Absolute(91和182g a.i./ha)、Quilt(101和160g a.i./ha)、Tilt(126g a.i./ha)、Quadris(170g a.i./ha)、Headline(82和110g a.i./ha)]相似。与商用标准品相比,观察到最高比率的化合物4提高了产量。
以上描述是为了说明本发明,并不能解释为其限制。本发明由下列权利要求来界定,权利要求等同方案包括在其中。
Claims (23)
2.权利要求1的化合物,其中R1为4-氯苯基、2,4-二氯苯基或2,4-二氟苯基。
3.权利要求1的化合物,其中R2为3-吡啶基。
4.权利要求1的化合物,其中R3为烷基;任选被卤素取代的苯基;噻吩基或烷基甲硅烷基。
5.权利要求1的化合物,其中R3为苯基、3-氯苯基、4-氯苯基、4-氟苯基、3,5-二氟苯基、2-噻吩基、3-噻吩基、叔丁基或三甲基甲硅烷基。
6.权利要求1的化合物或其盐,其中R4为H。
7.权利要求1的化合物或其盐,其中:
R1为被卤素取代的苯基;
R2为吡啶基;
R3为烷基;任选被卤素、烷基或烷氧基取代的苯基;噻吩基;或烷基甲硅烷基;和
R4为H。
8.权利要求7的化合物,其中R1为4-氯苯基、2,4-二氯苯基或2,4-二氟苯基。
9.权利要求7的化合物,其中R2为3-吡啶基。
10.权利要求7的化合物,其中R3为苯基、3-氯苯基、4-氯苯基、4-氟苯基、3,5-二氟苯基、2-噻吩基、3-噻吩基、叔丁基或三甲基甲硅烷基。
11.选自下列的权利要求1的化合物和其盐:
3-(2,4-二氯苯基)-4-[(3-吡啶基)羟甲基]-5-(2-噻吩基)异唑(化合物12);
12.一种用于防治和预防植物病原微生物的组合物,该组合物包含权利要求1的化合物与可接受载体。
13.权利要求12的组合物,该组合物进一步包含至少一种另外的杀真菌剂或***获得性抗性诱导剂。
14.一种防治或预防病原微生物侵染栽培植物的方法,该方法包括:
将权利要求1的化合物以有效防治所述微生物的量施用于所述植物、其部份或其所在地。
15.权利要求14的方法,其中所述微生物为真菌生物体。
16.权利要求15的方法,其中所述真菌生物体选自小麦壳针孢、Stagonospora nodorum、致病疫霉、灰葡萄孢、Sclerotinia homoeocarpa和隐匿柄锈菌。
17.一种防治或预防病原微生物侵染植物繁殖材料的方法,该方法包括:
将权利要求1的化合物以有效防治所述微生物的量施用于所述植物繁殖材料。
18.权利要求17的方法,其中所述植物繁殖材料包括种子。
19.权利要求17的方法,其中所述微生物为真菌生物体。
21.权利要求20的方法,其中所述溶剂为惰性溶剂,而所述碱为有机碱。
22.权利要求20的方法,其中所述溶剂为质子溶剂,而所述碱为无机碱。
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EP2595985A1 (en) | 2010-07-19 | 2013-05-29 | Syngenta Participations AG | Isoxazole, isothiazole, furane and thiophene compounds as microbicides |
BR112013001265A2 (pt) | 2010-07-19 | 2016-05-17 | Syngenta Participations Ag | microbicidas |
RU2478288C2 (ru) * | 2011-06-23 | 2013-04-10 | Федеральное государственное образовательное учреждение Высшего профессионального образования КАБАРДИНО-БАЛКАРСКАЯ ГОСУДАРСТВЕННАЯ АКАДЕМИЯ ИМЕНИ В.М. КОКОВА | Способ стимуляции роста и развития озимой пшеницы |
WO2013007550A1 (en) | 2011-07-08 | 2013-01-17 | Syngenta Participations Ag | Fungicide mixtures |
WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
CN103172584A (zh) * | 2013-03-15 | 2013-06-26 | 吉林大学 | 双异噁唑甲醚衍生物及制备方法 |
JP2017078022A (ja) * | 2014-02-28 | 2017-04-27 | クミアイ化学工業株式会社 | イソキサゾール誘導体及びそれを用いた農園芸用植物病害防除剤 |
BR112017006425B8 (pt) * | 2014-10-01 | 2023-05-16 | Daiichi Sankyo Co Ltd | Compostos derivados de isoxazol, seus usos, inibidores de isocitrato desidrogenase 1 mutante e da produção de d-2 hidroxiglutamato, agente antitumoral e composição farmacêutica compreendendo os mesmos |
CA3050864A1 (en) | 2017-01-26 | 2018-08-02 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
US11147272B2 (en) | 2017-04-10 | 2021-10-19 | Mitsui Chemicals Argro, Inc. | Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients |
EP3611166B1 (en) | 2017-04-10 | 2022-09-21 | Mitsui Chemicals Agro, Inc. | Pyridone compound, and agricultural and horticultural fungicide having this as active component |
CN110234627B (zh) | 2017-04-11 | 2023-09-01 | 三井化学植保株式会社 | 吡啶酮化合物及以吡啶酮化合物作为有效成分的农园艺用杀菌剂 |
US20200231607A1 (en) | 2017-05-03 | 2020-07-23 | Bayer Aktiengesellschaft | Trisubstitutedsilylheteroaryloxyquinolines and analogues |
WO2018225829A1 (ja) | 2017-06-08 | 2018-12-13 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
CN111712495A (zh) * | 2017-12-22 | 2020-09-25 | 拜耳公司 | 羟基异*唑啉及其衍生物 |
TWI828725B (zh) | 2018-07-25 | 2024-01-11 | 日商三井化學植保股份有限公司 | 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑 |
WO2020254492A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254489A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents |
BR112021025317A2 (pt) | 2019-06-21 | 2022-03-15 | Bayer Ag | Tienilhidroxiisoxazolinas e derivados das mesmas |
BR112021025305A2 (pt) | 2019-06-21 | 2022-02-01 | Bayer Ag | Hidroxi-isoxazolinas e uso das mesmas como fungicidas |
EP3986891A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254490A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents |
BR112021025700A2 (pt) | 2019-06-21 | 2022-02-08 | Bayer Ag | Hidróxi-isoxazolinas e derivados das mesmas |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0767170A1 (en) * | 1995-04-13 | 1997-04-09 | Taiho Pharmaceutical Co., Ltd. | Novel 4,6-diarylpyrimidine derivatives and salts thereof |
EP1449841A1 (en) * | 2003-02-19 | 2004-08-25 | Bayer CropScience SA | New fungicidal compounds |
WO2006016708A1 (en) * | 2004-08-12 | 2006-02-16 | Ishihara Sangyo Kaisha, Ltd. | Fungicidal composition containing acid amide derivative |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3914969A1 (de) * | 1989-05-02 | 1990-11-08 | Schering Ag | 5-substituierte 3-arylisoxazol-derivate, deren herstellung und verwendung als schaedlingsbekaempfungsmittel |
JPH05279339A (ja) * | 1992-01-22 | 1993-10-26 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
SE9302332D0 (sv) * | 1993-07-06 | 1993-07-06 | Ab Astra | New compounds |
ATE230727T1 (de) * | 1995-09-29 | 2003-01-15 | Shionogi & Co | Alpha-substituierte heterozyklische benzylderivate, zwischenverbindungen zu ihrer herstellung und pestizide die diese als aktiver bestandteil enthalten |
DE19546462A1 (de) * | 1995-12-13 | 1997-06-19 | Bayer Ag | Diarylacetylenketone |
AU2712097A (en) * | 1996-05-13 | 1997-12-05 | Shionogi & Co., Ltd. | Alpha-substituted benzyl ether derivatives and pesticides comprising the same as active ingredients |
DE19845004C2 (de) * | 1998-09-30 | 2002-06-13 | Infineon Technologies Ag | DRAM-Zellenanordnung und Verfahren zu deren Herstellung |
DE60039616D1 (de) * | 1999-08-13 | 2008-09-04 | Vertex Pharma | INHIBITOREN DER c-JUN N-TERMINALEN KINASE (JNK) UND ANDERE PROTEIN-KINASEN |
SE0102641D0 (sv) * | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
DE10360369A1 (de) * | 2003-12-22 | 2005-07-14 | Bayer Cropscience Ag | Amide |
-
2005
- 2005-09-09 JP JP2007531348A patent/JP4988576B2/ja not_active Expired - Fee Related
- 2005-09-09 EP EP05796586A patent/EP1794167A4/en not_active Withdrawn
- 2005-09-09 WO PCT/US2005/032080 patent/WO2006031631A1/en active Application Filing
- 2005-09-09 AU AU2005285130A patent/AU2005285130B2/en not_active Ceased
- 2005-09-09 KR KR1020077008114A patent/KR20070058599A/ko not_active Application Discontinuation
- 2005-09-09 CN CN2012100986613A patent/CN102731490A/zh active Pending
- 2005-09-09 BR BRPI0515108-2A patent/BRPI0515108A/pt not_active IP Right Cessation
- 2005-09-09 CN CN2009102080315A patent/CN101696221B/zh not_active Expired - Fee Related
- 2005-09-09 CA CA2579199A patent/CA2579199C/en not_active Expired - Fee Related
- 2005-09-09 MX MX2007002929A patent/MX2007002929A/es active IP Right Grant
- 2005-09-09 RU RU2007113188/04A patent/RU2392273C2/ru not_active IP Right Cessation
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- 2007-03-07 EG EGNA2007000253 patent/EG24509A/xx active
- 2007-03-08 CR CR8986A patent/CR8986A/es not_active Application Discontinuation
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0767170A1 (en) * | 1995-04-13 | 1997-04-09 | Taiho Pharmaceutical Co., Ltd. | Novel 4,6-diarylpyrimidine derivatives and salts thereof |
EP1449841A1 (en) * | 2003-02-19 | 2004-08-25 | Bayer CropScience SA | New fungicidal compounds |
WO2006016708A1 (en) * | 2004-08-12 | 2006-02-16 | Ishihara Sangyo Kaisha, Ltd. | Fungicidal composition containing acid amide derivative |
Also Published As
Publication number | Publication date |
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CA2579199A1 (en) | 2006-03-23 |
EP1794167A1 (en) | 2007-06-13 |
IL199786A (en) | 2011-10-31 |
CR8986A (es) | 2007-09-11 |
EG24509A (en) | 2009-08-19 |
EP1794167A4 (en) | 2009-10-21 |
IL181723A (en) | 2011-03-31 |
CA2579199C (en) | 2013-04-30 |
AU2005285130B2 (en) | 2011-09-15 |
AU2005285130A1 (en) | 2006-03-23 |
IL181723A0 (en) | 2007-07-04 |
US7977341B2 (en) | 2011-07-12 |
BRPI0515108A (pt) | 2008-07-01 |
CN101696221B (zh) | 2013-05-29 |
MX2007002929A (es) | 2007-08-16 |
IL209962A (en) | 2012-07-31 |
RU2392273C2 (ru) | 2010-06-20 |
JP4988576B2 (ja) | 2012-08-01 |
WO2006031631A1 (en) | 2006-03-23 |
JP2008512482A (ja) | 2008-04-24 |
KR20070058599A (ko) | 2007-06-08 |
US20080096843A1 (en) | 2008-04-24 |
CN101696221A (zh) | 2010-04-21 |
RU2007113188A (ru) | 2008-10-20 |
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