TW201617339A - 作爲殺真菌劑之巨環吡啶醯胺 - Google Patents
作爲殺真菌劑之巨環吡啶醯胺 Download PDFInfo
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- TW201617339A TW201617339A TW104135243A TW104135243A TW201617339A TW 201617339 A TW201617339 A TW 201617339A TW 104135243 A TW104135243 A TW 104135243A TW 104135243 A TW104135243 A TW 104135243A TW 201617339 A TW201617339 A TW 201617339A
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- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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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
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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
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
本揭露係有關於具化學式I之巨環吡啶醯胺,及其等作為殺真菌劑之用途。
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Description
本申請案主張於2014年10月28日申請之美國臨時專利申請序號第62/069452號案之利益,此案在此被明確併入以供參考。
本發明係有關於作為殺真菌劑之巨環吡啶醯胺。
殺真菌劑係作為保護及/或治療植物抵抗受農業相關真菌損害之天然或合成來源的化合物。一般,無單一殺真菌劑可用於所有情況。因此,研究係持續製造可具有較佳性能,更易使用,及成本較少之殺真菌劑。
本揭露係有關於巨環吡啶醯胺,及其等作為殺真菌劑之用途。本揭露之化合物可提供對抗子囊菌類、擔子菌類、半知菌類,及卵菌類之保護。
本揭露之一實施例可包含具化學式I之化合物:
X係氫或C(O)R3;Y係氫、C(O)R3,或Q;Q係
R1氫、烷基、芳基、醯基,或矽烷基,每一者係選擇性地以0、1或多數個R6取代,R2係-(CH2)nR8,其中,n係0與4間之整數,每一者選擇性地以0、1或多個R6取代;R3係烷氧基或苯甲氧基,每一者選擇性地以0、1,或多數個R6取代;R4係氫、-C(O)R5,或-CH2OC(O)R5;R5係烷基、烷氧基,或芳基,每一者選擇性地以0、1,或多數個R6取代;R6係氫、烷基、芳基、醯基、鹵基、烯基、烷氧基、雜環基,或硫烷基,每一者係選擇性地以0、1,或多數個R7取代;R7係氫、烷基、芳基、烷氧基,或鹵基。
R8係氫、烷基、烯基、芳基、雜環基,或硫烷基,每一者係以0、1,或多數個R6取代。
本揭露之另一實施例可包括用於控制或預防真菌攻擊之一殺真菌劑組成物,包含上述之化合物及一植物學可接受之載劑材料。
本揭露之另一實施例可包括一種用於控制或預防真菌對植物攻擊之方法,此方法包括使一殺真菌劑有效量之一或多種上述化合物施用至真菌、植物,及與此植物相鄰之一區域的至少一者之步驟。
熟習此項技藝者會瞭解下列術語可於其等之定義內包含一般之"R"基團,例如,"術語烷氧基係指一-OR取代基"。亦需瞭解於下列術語之定義內,此等"R"基團係用於例示目的而被包括,且不應被闡釋為作為限制或上述化學式I之取代基所限制。
術語"烷基"係指一分支、未分支,或飽和之環狀碳鏈,不受限地包括甲基、乙基、丙基、丁基、異丙基、異丁基、第三丁基、戊基、己基、環丙基、環丁基、環戊基、環己基等。
術語"烯基"係指含有一或多個雙鍵之一分支、未分支,或環狀之碳鏈,不受限地包括乙烯基、丙烯基、丁烯基、異丙烯基、異丁烯基、環丁烯基、環戊烯基、環己烯基等。
術語"炔基"係指含有一或多個三鍵之一分支或未分支之碳鏈,不受限地包括丙炔基、丁炔基等。
術語"芳基"及“Ar”係指含有0個雜原子之任何芳香族環,單或二環狀。
術語"雜環基"係指含有一或多個雜原子之任何芳香族或非芳香族之環,單或二環狀。
術語"烷氧基"係指一-OR取代基。
術語"醯氧基"係指一-OC(O)R取代基。
術語"氰基"係指一-C≡N取代基。
術語"羥基"係指一-OH取代基。
術語"胺基"係指一-N(R)2取代基。
術語"芳基烷氧基"係指-O(CH2)nAr,其中,n係選自1、2、3、4、5,或6之列示的整數。
術語"鹵烷氧基"係指一-OR-X取代基,其中,X係Cl、F、Br,或I,或其等之任何組合。
術語"鹵烷基"係指以Cl、F、I,或Br,或此等之任何組合取代之一烷基。
術語"鹵素"或"鹵基"係指一或多個以F、Cl、Br,及I定義之鹵素原子。
術語"硝基"係指一-NO2取代基。
術語硫烷基係指一-SR取代基。
於本揭露各處,提及具化學式I之化合物係讀作包括其非鏡像異構物、鏡像異構物,及混合物。於另一實施例,化學式(I)係價作亦包括其鹽類或水合物。例示之鹽類不受限地包括氫氯酸鹽、氫溴酸鹽,及氫碘酸鹽。
熟習此項技藝者亦瞭解除非其它指示外,額外取
代亦可容許,只要化學鍵結及應變能之規則被滿足且產物仍展現殺真菌劑作用。
本揭露之另一實施例係具化學式I之化合物用於保護植物對抗受致植物病生物體攻擊或治療受致植物病生物體感染的植物之用途,包含使具化學式I之一化合物,或包含此化合物之一組成物施用至土壤、一植物、一植物之一部份、葉子,及/或根。
額外地,本揭露之另一實施例係可用於保護植物對抗受致植物病生物體攻擊及/或治療受致植物病生物體感染的植物之一組成物,包含具化學式I之一化合物,及一植物學可接受之載劑材料。
本揭露之化合物可藉由任何各種已知技術,以化合物或以包含此等化合物之調配物施用。例如,化合物可於損及植物之商業價值施用至植物之根或葉子用以控制各種真菌。材料可以任何一般使用之調配物類型之型式施用,例如,以溶液、塵粉、可弄濕粉末、可流動濃縮物,或可乳化濃縮物。
較佳地,本揭露之化合物係以包含一或多種具化學式I之化合物及一植物學可接受的載劑之一調配物的型式施用。濃縮調配物可分散於水或其它液體中以供施用,
或調配物可為塵粉狀或顆粒狀,然後,可於未進一步處理下被施用。調配物可依據於農業化學技術上傳統之程序製備。
本揭露考量到藉此可使一或多種化合物被調配以供遞送及作為一殺真菌劑之所有載體。典型上,調配物可以水性懸浮液或乳化液施用。此等懸浮液或乳化液可自水溶性、水可懸浮或可乳化之調配物製造,此等調配物係固體,通常係稱為可弄濕粉末;或液體,通常稱為可乳化濃縮物、水性懸浮液,或懸浮濃縮物。如可輕易瞭解般,可被添加此等化合物之任何材料可被使用,只要其產生所欲用途且未顯著影響此等化合物作為抗真菌劑之活性。
可被密實化形成水可分散顆粒之可弄濕粉末可包含具有一或多種具化學式I之化合物、一惰性載劑,及界面活性劑之一緻密混合物。以可弄濕粉末總重量為基準,可弄濕粉末中之化合物濃度可為從約10重量%至約90重量,更佳係約25重量%至約75重量%。於可弄濕粉末調配物之製備,化合物可與任何細碎固體調合,諸如,葉蠟石、滑石、白堊、石膏、富勒氏土、皂土、厄帖浦土、澱粉、乾酪素、麩粉、蒙脫土黏土、矽藻土、純化矽酸鹽等。於此等操作,細碎載劑及界面活性劑典型上係與化合物摻合及研磨。
具化學式I之化合物之可乳化濃縮物可包含一便利濃度,諸如,以濃縮物總重量為基準,於一適合液體中從約1重量%至約50重量%之化合物。化合物可溶於為可
與水混溶之溶劑或不可與水混溶之有機溶劑及乳化劑之混合物的一惰性載劑中。濃縮物可以水及油稀釋,形成呈水中油乳化液型式之噴灑混合物。有用之有機溶劑包括芳香族化合物,特別是高沸點石油之萘及烯烴部份,諸如,重芳香族石腦油。其它有機溶劑亦可被使用,例如,萜系溶劑,包括松香衍生物,脂族酮類,諸如,環己酮,及錯合醇類,諸如,2-乙氧基乙醇。
可於此處有利使用之乳化劑可由熟習此項技藝者輕易判定,且包含各種非離子性、陰離子性、陽離子性,及兩性之乳化劑,或二或更多種乳化劑之摻合物。可用於製備可乳化濃縮物之非離子性乳化劑的例子包括聚烯烴二醇酯及烷基及芳基酚類、脂族醇類、脂族胺類,或脂肪酸類與環氧乙烷、環氧丙烷之縮合產物,諸如,以多元醇或聚氧化烯穩定化之乙氧基化烷基酚類及羧酸酯。陽離子性乳化劑包括四級銨化合物及脂肪胺鹽。陰離子性乳化劑包括烷基芳磺酸之油可溶鹽類(例如,鈣)、硫酸聚乙二醇醚之油可溶類鹽,及磷酸聚乙二醇醚之適合鹽類。
可用於製備本揭露化合物之可乳化濃縮物的代表性有機液體係芳香族液體,諸如,二甲苯、丙基苯分餾物;或混合式萘分餾物、礦物油、經取代之芳香族有機液體,諸如,苯二甲酸二辛酯;煤油;各種脂肪酸之二烷基醯類,特別是脂肪二醇類及二醇衍生物(諸如,二乙二醇之正丁醚、乙醚,或甲醚,三乙二醇之甲醚)之二甲基醯胺,石油分餾物或烴類,諸如,礦物油、芳香族溶劑、石蠟油
等;蔬菜油,諸如,大豆油、菜籽油、橄欖油、蓖麻油、葵花籽油、椰子油、玉米油、棉籽油、亞麻籽油、棕櫚油、花生油、紅花油、芝麻油、桐油等;上述蔬菜油之酯等。二或更多種有機液體之混合物亦可用於製備可乳化濃縮物。有機液體包括二甲苯,及丙基苯分餾物,且二甲苯於某些情況係最佳。表面活性分散劑典型上用於液體調配物,且以分散劑與一或多種此等化合物之混合重量為基準,係從0.1至20重量%之量。調配物亦可含有其它可相容之添加劑,例如,用於農業之植物生長調節劑及其它生物活性化合物。
以水性懸浮液總重量為基準,水性分散液包含以範圍從約1至約50重量%之濃度分散於一水性載體中之一或多種水不可溶之具化學式I之化合物。浮液係藉由使一或多種化合物細微研磨,及使經研磨之材料劇烈混合於包含水及自選自如上探討相同型式之界面活性劑之一載體內而製備。諸如無機鹽類及合成或天然膠之其它組份亦可被添加以增加水性載體之密度及黏度。
具化學式I之化合物亦可以顆粒狀調配物施用,其等係特別有用於施用至土壤。以化合物之顆粒狀調配物總重量為基準,顆粒狀調配物一般含有從約0.5至約10重量%,其係分散於完全或大部份由粗碎惰性材料組成之一惰性載劑中,諸如,厄帖浦土、皂土、矽藻土、黏土,或一相似不昂貴物質。此等調配物一般係藉由使化合物溶解於一適合溶劑,且使其施用至已預成型至於從約0.5至約3mm
之適當顆粒尺寸的一顆粒狀載劑而製備。一適合溶劑係化合物於其內係實質上或完全可溶之一溶劑。此等調配物亦可藉由製作載劑及化合物與溶劑之一糰狀物或糊狀物,及粉碎與乾燥獲得所欲顆粒狀粒子而製備。
合有具化學式I之化合物的塵粉可藉由使呈粉末型式之一或多種化合物與一適合塵粉狀農業載劑(諸如,高嶺土、經研磨之火山岩等)緻密混合而製備。以塵粉總重量為基準,塵粉適合地含有從約1至約10重量%之化合物。
調配物可額外地含有佐劑界面活性劑,以增強化合物於目標作物及生物體上之沉積、弄濕,及滲透。此等佐劑界面活性劑可選擇性地作為調配物之組份或作為一桶混合物。以水之噴灑體積為基準,佐劑界面活性劑的量典型上會從0.01至1.0體積%作改變,較佳係0.05至0.5體積%。適合之佐劑界面活性劑不受限地包括乙氧基化壬基酚類、乙氧基化合成或天然醇類、酯類或磺基琥珀酸類之鹽類、乙氧基化有機矽酮類、乙氧基化脂肪胺類、界面活性劑與礦物或蔬菜油之摻合物、作物油濃縮物(礦物油(85%)+乳化劑(15%));壬基酚乙氧化物;苯甲基椰油烷基二甲基四級銨鹽;石油烴、烷基酯類、有機酸,及陰離子性界面活性劑之摻合物;C9-C11烷基聚糖苷;磷酸鹽化醇乙氧化物;天然一級醇(C12-C16)乙氧化物;二第二丁基酚EO-PO嵌段共聚物;甲基封端之聚矽氧烷;壬基酚乙氧化物+尿素銨硝酸鹽;乳化甲基化籽油;十三烷醇(合成)乙氧化物(8EO);脂胺乙氧化物(15 EO);PEG(400)二油酸酯-99。調配物亦可
含有水中油型乳化液,諸如,於美國專利申請序號第11/495,228號案中揭露者,此案之揭露係於此處明確併入以供參考。
調配物可選擇性地包含含有其它殺蟲劑化合物之組合物。此等額外殺蟲劑化合物可為於選用於施用之介質中可與本揭露之化合物相容且對於本案化合物之活性無拮抗性之殺真菌劑、殺昆蟲劑、除草劑、殺棉蟲劑、殺蟎劑、殺節肢動物劑、殺細菌劑,或此等之組合。因此,於此等實施例,其它殺蟲劑化合物係作為相同或不同殺蟲劑用途之一補充毒劑。組合物中的具化學式I之化合物及殺蟲劑化合物一般係以從1:100至100:1之重量比率存在。
本揭露之化合物亦可與其它殺真菌劑組合形成殺真菌劑混合物及其增效混合物。本揭露之殺真菌劑化合物通常係與一或多種其它殺真菌劑結合施用,以控制較廣之各種非所欲疾病。當與其它殺真菌劑結合使用時,本請求化合物可以其它殺真菌劑調配,與其它殺真菌劑桶式混合,或與其它殺真菌劑依序施用,此等其它殺真菌劑可包括2-(氰硫基甲硫基)-苯并噻唑、2-苯基酚、8-羥基喹啉硫酸鹽、滅脫定(ametoctradin)、安美速(amisulbrom)、抗霉素(antimycin)、白粉寄生菌(Ampelomyces quisqualis)、阿扎康唑(azaconazole)、亞托敏(azoxystrobin)、枯草桿菌(Bacillus subtilis)、枯草桿菌株QST713、本達樂(benalaxyl)、免賴得(benomyl)、苯噻菌胺-異丙基(benthiavalicarb-isopropyl)、苯并烯氟菌唑(benzovindiflupyr)苯甲基胺基苯-磺酸鹽
(BABS)、碳酸氫鹽類、聯苯、葉枯唑(bismerthiazol)、比多農(bitertanol)、聯苯吡菌胺(bixafen)、滅瘟素-S(blasticidin-S)、硼砂、波爾多混合劑(Bordeaux mixture)、白克列(boscalid)、溴克座(bromuconazole)、布瑞莫(bupirimate)、多硫化鈣、敵菌丹(captafol)、克菌丹(captan)、貝芬替(carbendazim)、萎銹靈(carboxin)、加普胺(carpropamid)、春芹酮(carvone)、氯芬酮(chlazafenone)、地茂散(chloroneb)、四氯異苯腈(chlorothalonil)、乙菌利(chlozolinate)、盾殼霉菌(Coniothyrium minitans)、氫氧化銅、辛酸銅、氧氯化銅、硫酸銅、硫酸銅(三鹽基)、氧化亞銅、氰霜唑(cyazofamid)、環氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、環克座(cyproconazole)、嘧菌環胺(cyprodinil)、棉隆(dazomet)、咪菌威(debacarb)、伸乙基雙-(二硫代氨基甲酸)二銨、益發靈(dichlofluanid)、二氯芬(dichlorophen)、雙氯氰菌胺(diclocymet)、達滅淨(diclomezine)、氯硝胺(dichloran)、乙霉威(diethofencarb)、待克利(difenoconazole)、野燕枯離子(difenzoquat ion)、二氟林(diflumetorim)、達滅芬(dimethomorph)、醚菌胺(dimoxystrobin)、烯唑醇(diniconazole)、烯唑醇-M、敵蟎通(dinobuton)、敵蟎普(dinocap)、二苯胺、腈硫醌(dithianon)、嗎菌靈(dodemorph)、嗎菌靈硫酸鹽、多果定(dodine)、多果定游離鹼、克瘟散(edifenphos)、烯肟菌酯(enestrobin)、烯廂菌酯(enestroburin)、依普座(epoxiconazole)、唑菌胺(ethaboxam)、乙氧喹(ethoxyquin)、依得利(etridiazole)、凡殺同(famoxadone)、
咪唑菌酮(fenamidone)、芬瑞莫(fenarimol)、芬克座(fenbuconazole)、甲呋醯胺(fenfuram)、環醯菌胺(fenhexamid)、稻瘟醯胺(fenoxanil)、拌種咯(fenpiclonil)、苯銹啶(fenpropidin)、芬普福(fenpropimorph)、胺苯吡菌酮(fenpyrazamine)、三苯錫(fentin)、乙酸三苯錫(fentin acetate)、氫氧三苯錫(fentin hydroxide)、福美鐵(ferbam)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、咯菌腈(fludioxonil)、氟嗎啉(flumorph)、氟吡菌胺(fluopicolide)、氟吡菌醯胺(fluopyram)、唑呋草(fluoroimide)、氟嘧菌酯(fluoxastrobin)、氟喹唑(fluquinconazole)、氟矽唑(flusilazole)、氟硫滅(flusulfamide)、氟噻菌淨(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、氟唑菌醯胺(fluxapyroxad)、滅菌丹(folpet)、甲醯胺、三乙膦酸(fosetyl)、三乙膦酸鋁、麥穗寧(fuberidazole)、呋霜靈(furalaxyl)、福拉比(furametpyr)、克熱淨(guazatine)、克熱淨乙酸鹽、GY-81、六氯苯、菲克利(hexaconazole)、殺紋寧(hymexazol)、依滅列(imazalil)、依滅列硫酸鹽、易胺座(imibenconazole)、克熱淨(iminoctadine)、克熱淨三乙酸鹽、克熱淨烷苯磺酸鹽、3-碘-2-丙基丁基胺基甲酸酯(iodocarb)、種菌唑(ipconazole)、依芬吡唑酮(ipfenpyrazolone)、丙基喜樂松(iprobenfos)、依普同(iprodione)、異丙菌威(iprovalicarb)、亞賜圃(isoprothiolane)、3-(二氟甲基)-1-甲基-N-[1,2,3,4-四氫-9-(1-甲基乙基)-1,4-亞甲基萘-5-基]-1H-吡唑-4-甲醯胺(isopyrazam)、異噻菌胺(isotianil)、嘉賜黴菌(kasugamycin)、嘉賜黴菌氫氯酸鹽水
合物、克收欣甲基(kresoxim-methyl)、昆布多糖(laminarin)、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamid)、錳乃浦(maneb)、右滅達樂(mefenoxam)、滅派林(mepanipyrim)、滅普寧(mepronil)、敵蟎普(meptyl-dinocap)、氯化汞、氧化汞、氯化亞汞、滅達樂(metalaxyl)、滅達樂-M、斯美地(metam)、斯美地銨鹽、斯美地鉀鹽、斯美地鈉鹽、滅特座(metconazole)、滅速克(methasulfocarb)、碘甲烷、異硫氰酸甲酯、免得爛(metiram)、苯氧菌胺(metominostrobin)、滅芬農(metrafenone)、米多黴素(mildiomycin)、邁克尼(myclobutanil)、代森鈉(nabam)、酞菌酯(nitrothal-isopropyl)、尼瑞莫(nuarimol)、辛噻酮(octhilinone)、呋醯胺(ofurace)、油酸(脂肪酸類)、肟醚菌胺(orysastrobin)、毆殺斯(oxadixyl)、快得寧(oxine-copper)、惡咪唑福馬酸鹽、嘉保信(oxycarboxin)、披扶座(pefurazoate)、平克座(penconazole)、賓克隆(pencycuron)、戊苯吡菌胺(penflufen)、五氯酚、月桂酸五氯苯酯、吡噻菌胺(penthiopyrad)、乙酸苯汞、膦酸、熱必斯(phthalide)、啶氧菌酯(picoxystrobin)、保粒黴素B(polyoxin B)、保粒黴素、保粒黴素丁(polyoxorim)、碳酸氫鉀、羥基喹啉硫酸鉀、撲殺熱(probenazole)、撲克拉(prochloraz)、撲滅寧(procymidone)、霜黴威(propamocarb)、普拔克(propamocarb hydrochloride)、普克利(propiconazole)、甲基鋅乃浦(propineb)、丙氧喹啉(proquinazid)、丙硫菌唑(prothioconazole)、百克敏(pyraclostrobin)、唑胺菌酯
(pyrametostrobin)、唑菌酯(pyraoxystrobin)、白粉松(pyrazophos)、甲基{2-氯-5-[(1E)-1-(6-甲基-2-吡啶基甲氧亞胺基)乙基]芐基}胺基甲酸酯(pyribencarb)、稗草丹(pyributicarb)、比芬諾(pyrifenox)、派美尼(pyrimethanil)、(5-氯-2-甲氧基-4-甲基-3-吡啶基)(4,5,6-三甲氧基-鄰甲苯基)甲酮(pyriofenone)、百快隆(pyroquilon)、莫克草(quinoclamine)、快諾芬(quinoxyfen)、五氯硝苯(quintozene)、大虎杖(Reynoutria sachalinensis)萃取物、N-[2-[1,1’-雙環丙基]-2-基苯基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺(sedaxane)、矽噻菌胺(silthiofam)、矽氟唑(simeconazole)、2-苯基苯氧化鈉、碳酸氫鈉、五氯苯氧化鈉、螺環菌胺(spiroxamine)、硫、SYP-Z048、焦油類、得克利(tebuconazole)、6-三級丁基-8-氟-2,3-二甲基-4-喹啉乙酸(tebufloquin)、四氯硝基苯(tecnazene)、四克利(tetraconazole)、腐絕(thiabendazole)、賽氟滅(thifluzamide)、甲基多保淨(thiophanate-methyl)、得恩地(thiram)、噻醯菌胺(tiadinil)、脫克松-甲基(tolclofos-methyl)、甲基益發靈(tolylfluanid)、三泰芬(triadimefon)、三泰隆(triadimenol)、三挫磷(triazoxide)、三賽唑(tricyclazole)、三得芬(tridemorph)、三氟敏(trifloxystrobin)、賽福座(triflumizole)、賽福寧(triforine)、滅菌唑(triticonazole)、維利黴素(validamycin)、N-[(1-甲基乙氧基)羰基]-L-纈胺醯基-3-(4-氯苯基)-β-胺基丙酸甲酯(valifenalate)、維利非那(valiphenal)、免克寧(vinclozolin)、鋅乃浦(zineb)、福美鋅(ziram)、座賽胺
(zoxamide)、假絲酵母(Candida oleophila)、尖鐮胞菌(Fusarium oxysporum)、黏帚黴素(Gliocladium spp.)、大伏革菌(Phlebiopsis gigantean)、淺灰綠鏈黴菌(Streptomyces griseoviridis)、木黴菌(Trichoderma spp.)、(RS)-N-(3,5-二氯苯基)-2-(甲氧基甲基)-琥珀醯亞胺、1,2-二氯丙烷、1,3-二氯-1,1,3,3-四氟丙酮水合物、1-氯-2,4-二硝基萘、1-氯-2-硝基丙烷、2-(2-十七烷基-2-咪唑啉-1-基)乙醇、2,3-二氫-5-苯基-1,4-二硫雜己環并1,1,4,4-四氧化物、乙酸2-甲氧基乙基汞、氯化2-甲氧基乙基汞、矽酸2-甲氧基乙基汞、3-(4-氯苯基)-5-甲基若丹林、4-(2-硝基丙-1-烯基)苯基硫氰酸酯、1-胺基丙基磷酸(ampropylfos)、敵菌靈(anilazine)、塞侖(azithiram)、多硫化鋇、拜耳(Bayer)32394、麥鏽靈(benodanil)、醌肟腙(benquinox)、1-(1,3-苯並噻唑-2-基)-異丙基尿素(bentaluron)、2-甲基丙基-2-氰基-3-[甲基(苯基甲基)氨基]-2-丙烯酸酯(benzamacril);2-甲基丙基-2-氰基-3-[甲基(苯基甲基)氨基]-2-丙烯酸異丁酯、抑菌啉(benzamorf)、百蟎克(binapacryl)、硫酸雙(甲基汞)、氧化雙(三丁基錫、得滅多(buthiobate)、鎘鈣銅鋅鉻酸鹽硫酸鹽、嗎菌威(carbamorph)、CECA、克氯綜(chlobenthiazone)、雙胺靈(chloraniformethan)、2-(2-氯苯基)-1H-苯并咪唑(chlorfenazole)、四氯喹啉(chlorquinox)、甘寶素(climbazole)、雙(3-苯基水楊酸)銅、鉻酸銅鋅、銅合浦單劑(cufraneb)、硫酸亞銅肼、福美銅氯(cuprobam)、環菌胺(cyclafuramid)、伏賜丁(cypendazole)、酯菌胺(cyprofuram)、
癸磷錫(decafentin)、二氯萘醌(dichlone)、賜克滅(dichlozoline)、苄氯三唑醇(diclobutrazol)、二甲嘧酚(dimethirimol)、敵蟎消(dinocton)、硝辛酯殺蟎劑(dinosulfon)、硝丁酯(dinoterbon)、雙硫氧吡啶(dipyrithione)、普得松(ditalimfos)、多地辛(dodicin)、肼菌酮(drazoxolon)、EBP、ESBP、乙環唑(etaconazole)、益地安(etem)、乙啼酷(ethirim)、敵磺鈉(fenaminosulf)、咪菌腈(fenapanil)、種衣酯(fenitropan)、三氟苯唑(fluotrimazole)、二甲呋醯胺(furcarbanil)、呋菌唑(furconazole)、順式呋菌唑、拌種胺(furmecyclox)、呋甲硫菌靈(furophanate)、2-十七烷基-2-咪唑乙酸酯(glyodine)、灰黃黴素(griseofulvin)、丙烯酸喹啉酯(halacrinate)、海克力士(Hercules)3944、(RS)-(O-環己基O,S-二乙基硫代磷酸酯)(hexylthiofos)、ICIA0858、壬氧磷胺(isopamphos)、3-(3,5-二氯苯基)-1-異戊醯基乙內醯脲(isovaledione)、巴斯丹(mebenil)、苯并威(mecarbinzid)、間氯敵菌酮(metazoxolon)、呋菌胺(methfuroxam)、雙氰安甲基汞、噻菌胺(metsulfovax)、代森環(milneb)、粘氯酸酐、滅克寧(myclozolin)、N-3,5-二氯苯基-琥珀醯亞胺、N-3-硝苯基衣糠醯亞胺、納他黴素(natamycin)、N-乙基汞基-4-甲苯磺醯苯胺、雙(二甲基二硫氨基甲酸)鎳、OCH、二甲基二硫氨基甲酸苯基汞、硝酸苯基汞、氯瘟磷(phosdiphen)、胺丙威(prothiocarb);胺丙威氫氯酸鹽、賜加落(pyracarbolid)、雙滴保(pyridinitril)、氯甲氧吡啶(pyroxychlor)、氯吡根呋醚(pyroxyfur)、喹烯酮(quinacetol);喹烯酮硫酸鹽、醌菌腙
(quinazamid)、喹克座(quinconazole)、吡咪唑(rabenzazole)、水楊醯苯胺(salicylanilide)、SSF-109、戊苯碸(sultropen)、福美雙聯(tecoram)、N,N’-[3-(4-氯苯基)-2-(甲亞胺)-4,5-四氫噻唑二亞基]雙[1,1,1-三氟甲胺](thiadifluor)、噻菌腈(thicyofen)、硫氯苯亞胺(thiochlorfenphim)、多保淨(thiophanate)、克殺蟎(thioquinox)、5-異硫氰酸-N,N,3-三甲基-o-對甲氧苯甲醯胺(tioxymid)、三唑磷胺(triamiphos)、嘧菌醇(triarimol)、丁三唑(triazbutil)、水楊菌胺(trichlamide)、福美甲胂(urbacide)、氰菌胺(zarilamid),及此等之任何組合。
另外,此處所述之化合物可與於選供施用之介質中可與本揭露之化合物相容,且對於用以形成殺蟲混合物及其協同作用混合物之本化合物的活性不具對抗性之包含殺昆蟲劑、殺線蟲劑、殺蟎劑、殺節肢動物劑、殺細菌劑或此等之組合的其它殺蟲劑組合。本揭露之殺真菌化合物可與一或多種其它殺蟲劑結合施用,以控制更廣泛之各種非所欲之害蟲。當與其它殺蟲劑結合使用時,本請求化合物可與其它殺蟲劑調配,與其它殺蟲劑桶式混合,或與其它殺蟲劑依序施用。典型之殺昆蟲劑不受限地包含:1,2-二氯丙烷、阿巴汀(abamectin)、毆殺松(acephate)、亞滅培(acetamiprid)、家蠅磷(acethion)、乙醯蟲腈(acetoprole)、阿納寧(acrinathrin)、丙烯腈、棉鈴威(alanycarb)、得滅克(aldicarb)、涕滅碸威(aldoxycarb)、阿特靈(aldrin)、亞列寧(allethrin)、阿洛胺菌素(allosamidin)、除害威(allyxycarb)、
α-賽滅寧(cypermethrin)、α-蛻皮激素、α-安殺番(endosulfan)、賽硫磷(amidithion)、滅害威(aminocarb)、阿米通(amiton)、草酸阿米通、三亞蟎(amitraz)、毒藜鹼(anabasine)、乙基殺撲磷(athidathion)、印楝素(azadirachtin)、亞滅松(azamethiphos)、乙基谷速松(azinphos)、甲基谷速松、偶氮磷(azothoate)、六氟矽酸鋇、椒菊酯(barthrin)、免敵克(bendiocarb)、免扶克(benfuracarb)、免速達(bensultap)、β-賽扶寧(cyfluthrin)、β-賽滅寧(cypermethrin)、畢芬寧(bifenthrin)、百亞列寧(bioallethrin)、苄呋烯菊酯(bioethanomethrin)、生物氯菊酯(biopermethrin)、雙三氟蟲脲(bistrifluron)、硼砂、硼酸、溴苯烯磷(bromfenvinfos)、保滿丹(bromocyclen)、溴-滴滴涕(DDT)、溴磷松(bromophos)、乙基溴磷松、必克蝨(bufencarb)、布芬淨(buprofezin)、畜蟲威(butacarb)、佈伏斯(butathiofos)、佈嘉信(butocarboxim)、布托酯(butonate)、丁酮碸威(butoxycarboxim)、硫線磷(cadusafos)、砷酸鈣、多硫化鈣、毒殺芬(camphechlor)、氯滅殺威(carbanolate)、胺甲(carbaryl)、加保扶(carbofuran)、二硫化碳、四氯化碳、加芬松(carbophenothion)、丁基加保扶(carbosulfan)、培丹(cartap)、培丹氫氯酸鹽、剋安勃(chlorantraniliprole)、冰片丹(chlorbicyclen)、可氯丹(chlordane)、十氯酮、氯苯甲脒(chlordimeform)、氯苯甲脒氫氯酸鹽、氯氧磷(chlorethoxyfos)、克凡派(chlorfenapyr)、氯芬松(chlorfenvinphos)、克福隆(chlorfluazuron)、氯甲磷(chlormephos)、氯仿、氯化苦(chloropicrin)、氯辛硫磷
(chlorphoxim)、滅蟲吡啶(chlorprazophos)、陶斯松(chlorpyrifos)、甲基陶斯松、克硫松(chlorthiophos)、可芬諾(chromafenozide)、第I型瓜菊酯、第II型瓜菊酯、瓜菊酯類、順式苄呋菊酯、除線威(cloethocarb)、氯氰碘柳胺(closantel)、可尼丁(clothianidin)、乙醯亞砷酸銅、砷酸銅、萘酸銅、油酸銅、蠅毒磷(coumaphos)、畜蟲磷(coumithoate)、克羅米通(crotamiton)、丁烯磷(crotoxyphos)、育畜磷(crufomate)、冰晶石、施力松(cyanofenphos)、氰乃松(cyanophos)、果蟲磷(cyanthoate)、氰蟲醯胺(cyantraniliprole)、環戊烯菊酯(cyclethrin)、乙氰菊酯(cycloprothrin)、賽扶寧(cyfluthrin)、賽洛寧(cyhalothrin)、賽滅寧(cypermethrin)、賽芬寧(cyphenothrin)、賽滅淨(cyromazine)、賽滅磷(cythioate)、滴滴涕(DDT)、去甲基克百威(decarbofuran)、第滅寧(deltamethrin)、甲基滅賜松(demephion)、甲基滅賜松-O、甲基滅賜松-S、內吸磷(demeton)、甲基內吸磷、內吸磷-O、甲基內吸磷-O、內吸磷-s、滅賜松(Demeton-S-methyl)、滅賜松碸、汰芬隆(diafenthiuron)、得拉松(dialifos)、矽藻土、大利松(diazinon)、異氯磷(dicapthon)、除線磷(dichlofenthion)、二氯松(dichlorvos)、甲苯酚基胺甲酸甲酯(dicresyl)、雙特松(dicrotophos)、環蟲腈(dicyclanil)、地特靈(dieldrin)、二福隆(diflubenzuron)、二羥丙茶鹼(dilor)、四氟甲醚菊酯(dimefluthrin)、甲氟磷(dimefox)、地麥威(dimetan)、大滅松(dimethoate)、苄菊酯(dimethrin)、二甲基亞硝胺
(dimethylvinphos)、敵蠅威(dimetilan)、消蟎酚(dinex)、消蟎酚二環己銨鹽、硝丙酚(dinoprop)、戊硝酚(dinosam)、達特南(dinotefuran)、苯蟲醚(diofenolan)、殺力松(dioxabenzofos)、二氧威(dioxacarb)、大克松(dioxathion)、二硫松(disulfoton)、3,4-二氯-N-(2-氰基苯基)-5-異噻唑甲醯胺(dithicrofos)、d-檸檬烯、DNOC、DNOC-銨鹽、DNOC-鉀鹽、DNOC-鈉鹽、多滅蟲(doramectin)、蛻皮甾酮(ecdysterone)、因滅汀(emamectin)、因滅汀苯甲酸鹽、EMPC、益避寧(empenthrin)、安殺番(endosulfan)、因毒磷(endothion)、安特靈(endrin)、EPN、保幼醚(epofenonane)、乙醯胺基阿維菌素(eprinomectin)、富右旋反式丙烯菊酯(esdépalléthrine)、益化利(esfenvalerate)、(RS)-[O-2,4-二氯苯基O-乙基S-硫代磷酸丙基酯](etaphos)、愛芬克(ethiofencarb)、愛殺松(ethion)、乙蟲腈(ethiprole)、益硫磷(ethoate-methyl)、普伏松(ethoprophos)、甲酸乙酯、乙基-DDD、二溴化乙烯、二氯化乙烯、環氧乙烷、依芬寧(etofenprox)、益多松(etrimfos)、EXD、胺磺磷(famphur)、芬滅松(fenamiphos)、抗蟎唑(fenazaflor)、樂乃松(fenchlorphos)、芬硫克(fenethacarb)、五氟苯菊酯(fenfluthrin)、撲滅松(fenitrothion)、丁基滅必蝨(fenobucarb)、N-(3,4-二氯苯基)六氫-1,3-二甲基-2,4,6-三側氧-5-嘧啶甲醯胺(fenoxacrim)、芬諾克(fenoxycarb)、吡氯氰菊酯(fenpirithrin)、芬普寧(fenpropathrin)、繁福松(fensulfothion)、芬殺松(fenthion)、乙基芬殺松、芬化利(fenvalerate)、芬普
尼(fipronil)、氟尼胺(flonicamid)、氟蟲醯胺(flubendiamide)、氟氰戊菊酯(flucofuron)、氟蟎脲(flucycloxuron)、護賽寧(flucythrinate)、嘧蟲胺(flufenerim)、氟芬隆(flufenoxuron)、三氟醚菊酯(flufenprox)、福化利(fluvalinate)、大福松(fonofos)、覆滅蟎(formetanate)、覆滅蟎氫氯酸鹽、福木松(formothion)、藻蟎威(formparanate)、藻蟎威氫氯酸鹽、丁苯硫磷(fosmethilan)、甲基氯吡磷(fospirate)、丁硫環磷(fosthietan)、呋線威(furathiocarb)、糠醛菊酯(furethrin)、γ-賽洛寧(cyhalothrin)、γ-HCH、合芬寧(halfenprox)、合芬隆(halofenozide)、HCH、HEOD、飛佈達(heptachlor)、飛達松(heptenophos)、速殺硫磷(heterophos)、六伏隆(hexaflumuron)、HHDN、愛美隆(hydramethylnon)、氰化氫、烯蟲乙酯(hydroprene)、5,6,7,8-四氫-2-甲基-4-喹啉基胺甲酸二甲酯(hyquincarb)、益達胺(imidacloprid)、依普寧(imiprothrin)、因得克(indoxacarb)、碘甲烷、IPSP、依殺松(isazofos)、碳氯靈(isobenzan)、水胺硫磷(isocarbophos)、異氯甲橋(isodrin)、亞芬松(isofenphos)、甲基亞芬松、滅必蝨(isoprocarb)、亞賜圃(isoprothiolane)、獲賜松(isothioate)、加福松(isoxathion)、依維菌素(ivermectin)、第I型茉酮菊酯、第II型茉酮菊酯、護粒松(jodfenphos)、第I型青春激素、第II型青春激素、第III型青春激素、氯戊環(kelevan)、烯蟲炔酯(kinoprene)、λ-賽洛寧(cyhalothrin)、砷酸鉛、里琵菌素(lepimectin)、福賜松(leptophos)、靈丹(lindane)、丙嘧硫磷(lirimfos)、祿芬隆(lufenuron)、噻唑磷(lythidathion)、馬拉
松(malathion)、特蟎腈(malonoben)、疊氮磷(mazidox)、滅加松(mecarbam)、四甲磷(mecarphon)、美納松(menazon)、美福松(mephosfolan)、氯化亞汞、倍硫磷亞碸(mesulfenfos)、美氟綜(metaflumizone)、滅克松(methacrifos)、達馬松(methamidophos)、滅大松(methidathion)、滅賜克(methiocarb)、殺蟲乙烯磷(methocrotophos)、納乃得(methomyl)、美賜平(methoprene)、甲氧滴滴涕(methoxychlor)、滅芬諾(methoxyfenozide)、溴甲烷、異硫氰酸甲酯、甲氯仿、二氯甲烷、美特寧(metofluthrin)、治滅蝨(metolcarb)、蟲酮(metoxadiazone)、美文松(mevinphos)、治克威(mexacarbate)、密滅汀(milbemectin)、倍脈心(milbemycin oxime)、丙胺氟磷(mipafox)、滅蟻樂(mirex)、殺蟲單(molosultap)、亞素靈(monocrotophos)、殺蟲單(monomehypo)、殺蟲單(monosultap)、茂硫磷(morphothion)、莫西菌素(moxidectin)、萘肽磷(naftalofos)、乃力松(naled)、萘、尼古丁、伏蟻靈(nifluridide)、烯啶蟲胺(nitenpyram)、硝乙脲噻唑(nithiazine)、戊氰威(nitrilacarb)、諾伐隆(novaluron)、多氟脲(noviflumuron)、歐滅松(omethoate)、歐殺滅(oxamyl)、滅多松(oxydemeton-methyl)、異亞碸磷(oxydeprofos)、碸拌磷(oxydisulfoton)、對-二氯苯、巴拉松(parathion)、甲基巴拉松、氟幼脲(penfluron)、五氯酚、百滅寧(permethrin)、芬硫磷(phenkapton)、酚丁滅寧(phenothrin)、賽達松(phenthoate)、福瑞松(phorate)、裕必松(phosalone)、硫環磷(phosfolan)、益滅松(phosmet)、對氯
硫磷(phosnichlor)、福賜米松(phosphamidon)、膦、巴賽松(phoxim)、甲基巴賽松、2-(二乙基胺基)-6-甲基-4-嘧啶基甲基甲基胺基磷酸酯(pirimetaphos)、比加普(pirimicarb)、必滅松(pirimiphos-ethyl)、亞特松(pirimiphos-methyl)、亞砷酸鉀、硫氰化鉀、4,4-滴滴涕(pp’-DDT)、普亞烈寧(prallethrin)、第I型早熟素、第II型早熟素、第III型早熟素、乙醯嘧啶磷(primidophos)、佈飛松(profenofos)、環丙氟靈(profluralin)、蜱虱威(promacyl)、普滅克(promecarb)、加護松(propaphos)、撲達松(propetamphos)、安丹(propoxur)、乙噻唑磷(prothidathion)、普硫松(prothiofos)、飛克松(prothoate)、4-[4-(4-氯苯基)-4-環丙丁基]-1-氟-2-苯氧基苯(protrifenbute)、白克松(pyraclofos)、1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(氟甲基)硫代]-5-[(吡基甲基)胺基]-1H-吡唑-3-甲腈(pyrafluprole)、白粉松(pyrazophos)、5-苄基-3-呋喃基甲基(E)-(1R,3R)-3-(2-甲氧羰基丙-1-烯基)-2,2-二甲基環丙烷羧酸酯(pyresmethrin)、第I型除蟲菊精、第II型除蟲菊精、除蟲菊精類、畢達本(pyridaben)、啶蟲丙醚(pyridalyl)、必芬松(pyridaphenthion)、1-乙醯基-1,2,3,4-四氫-3-[(3-吡啶基甲基)胺基]-6-[1,2,2,2-四氟-1-(三氟甲基)乙基]喹唑啉-2-酮(pyrifluquinazon)、畢汰芬(pyrimidifen)、嘧硫磷(pyrimitate)、1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(二氟甲基)硫代]-5-[(2-吡啶基甲基)胺基]-1H-吡唑-3-甲腈(pyriprole)、百利普芬(pyriproxyfen)、苦木(quassia)、拜裕松(quinalphos)、甲基拜裕松、畜寧磷(quinothion)、碘醚柳胺(rafoxanide)、
列滅寧(resmethrin)、魚藤酮(rotenone)、蘭尼汀(ryania)、藜蘆鹼(sabadilla)、八甲焦磷醯胺(schradan)、色拉菌素(selamectin)、矽護芬(silafluofen)、矽膠劑、亞砷酸鈉、氟化鈉、六氟矽酸鈉、硫氰酸鈉、蘇硫磷(sophamide)、賜諾特(spinetoram)、賜諾殺(spinosad)、螺甲蟎酯(spiromesifen)、螺蟲乙酯(spirotetramat)、5-氯-2-[4-氯-2-[[[(3,4-二氯苯基)胺基]羰基]苯氧基]苯磺酸(sulcofuron)、5-氯-2-[4-氯-2-[[[(3,4-二氯苯基)胺基]羰基]苯氧基]苯磺酸鈉、氟蟲胺(sulfluramid)、治螟磷(sulfotep)、氟啶蟲胺腈(sulfoxaflor)、磺醯氟、硫丙磷(sulprofos)、τ-福化利(fluvalinate)、噻蟎威(tazimcarb)、TDE、得芬諾(tebufenozide)、得芬瑞(tebufenpyrad)、丁基嘧啶磷(tebupirimfos)、得福隆(teflubenzuron)、汰福寧(tefluthrin)、亞培松(temephos)、TEPP、環戊烯丙菊酯(terallethrin)、托福松(terbufos)、四氯乙烷、樂本松(tetrachlorvinphos)、治滅寧(tetramethrin)、四氟醚菊酯(tetramethylfluthrin)、θ-賽滅寧(cypermethrin)、賽果培(thiacloprid)、賽速安(thiamethoxam)、苯噻乙硫磷(thicrofos)、抗蟲威(thiocarboxime)、硫賜安(thiocyclam)、硫賜安草酸鹽、硫敵克(thiodicarb)、硫伐隆(thiofanox)、硫滅松(thiometon)、殺蟲雙(thiosultap)、殺蟲雙二鈉、殺蟲雙單鈉、蘇力菌素(thuringiensin)、脫芬瑞(tolfenpyrad)、泰滅寧(tralomethrin)、拜富寧(transfluthrin)、反式百滅寧(transpermethrin)、三苯噻蟎吩(triarathene)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、樂乃松(trichlormetaphos)-3、毒壤膦
(trichloronat)、三氯丙氧磷(trifenofos)、三福隆(triflumuron)、混殺威(trimethacarb)、烯蟲硫酯(triprene)、繁米松(vamidothion)、(E)-1-(2,6-二氯-α,α,α-三氟-對甲苯基)-5-(4-羥基-3-甲氧苯亞甲基胺基)-4-三氟甲基硫吡唑-3-甲腈(vaniliprole)、XMC、滅爾蝨(xylylcarb)、ζ-賽滅寧(cypermethrin)、O-乙基S-[(3-甲基-5-異唑基)甲基]S-二硫代磷酸丙酯(zolaprofos),及此等之任何組合。
另外,此處所述之化合物可與於選供施用之介質中可與本揭露之化合物相容,且對於用以形成殺蟲混合物及其協同作用混合物之本化合物的活性不具對抗性之除草劑組合。本揭露之殺真菌化合物可與一或多種除草劑結合使用,以控制廣泛之各種非所欲的植物。當與除草劑結合使用時,本請求化合物可與除草劑調配,與除草劑桶式混合,或與除草劑依序施用。典型除草劑不受限地包含:4-CPA;4-CPB;4-CPP;2,4-D;3,4-DA;2,4-DB;3,4-DB;2,4-DEB;2,4-DEP;3,4-DP;2,3,6-TBA;2,4,5-T;2,4,5-TB;乙草胺(acetochlor)、亞喜芬(acifluorfen)、苯草醚(aclonifen)、丙烯醛(acrolein)、拉草(alachlor)、二丙烯草胺(allidochlor)、亞汰草(alloxydim)、烯丙醇、亞羅列克(alorac)、胺酮(ametridione)、草殺淨(ametryn)、胺草酮(amibuzin)、胺唑草酮(amicarbazone)、醯嘧磺隆(amidosulfuron)、環丙嘧啶酸(aminocyclopyrachlor)、氯胺吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、殺草強(amitrole)、氨基磺酸銨、莎稗磷(anilofos)、安尼速隆(anisuron)、磺草靈(asulam)、
阿特拉通(atraton)、草脫淨(atrazine)、草芬定(azafenidin)、四唑嘧磺隆(azimsulfuron)、滅蘇民(aziprotryne)、燕麥靈(barban)、BCPC、氟丁醯草胺(beflubutamid)、草除靈(benazolin)、醯苯草酮(bencarbazone)、氟草胺(benfluralin)、呋草黃(benfuresate)、免速隆(bensulfuron)、地散磷(bensulide)、本達隆(bentazone)、苯甲醯胺氧乙酸(benzadox)、雙苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、氟草黃(benzofluor)、新燕靈(benzoylprop)、苯噻隆(benzthiazuron)、雙環吡喃酮(bicyclopyrone)、治草醚(bifenox)、畢拉草(bilanafos)、雙草醚(bispyribac)、硼砂、克草(bromacil)、除草溴(bromobonil)、溴丁醯草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴莠敏(brompyrazon)、丁基拉草(butachlor)、布芬草(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、丁硫咪唑酮(buthidazole)、丁噻隆(buthiuron)、仲丁靈(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、丁酸鹽、二甲胂酸、苯酮唑(cafenstrole)、氯酸鈣、氰胺化鈣、(苯基亞胺基)二-2,1-乙二基雙(3,6-二氯-2-甲氧基苯甲酸酯)(cambendichlor)、除草隆(carbasulam)、草長滅(carbetamide)、5-三級丁基-1,2-唑基-3-基胺甲酸甲基酯(carboxazole)、3-[(甲氧羰基)胺基]苯基N-[1-(氯甲基)丙基]胺甲酸酯(chlorprocarb)、克繁草(carfentrazone)、CDEA、CEPC、甲氧基護谷(chlomethoxyfen)、克攔本(chloramben)、丁醯草胺(chloranocryl)、炔禾靈(chlorazifop)、氯阿淨
(chlorazine)、滅落寧(chlorbromuron)、氯草靈(chlorbufam)、1-(3-氯-4-乙氧苯基)-3,3-二甲基脲(chloreturon)、伐草克(chlorfenac)、燕麥酯(chlorfenprop)、氟咪殺(chlorflurazole)、整形醇(chlorflurenol)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、全滅草(chlornitrofen)、三氯丙酸(chloropon)、氯麥隆(chlorotoluron)、枯草龍(chloroxuron)、氯二甲酚(chloroxynil)、克普芬(chlorpropham)、氯磺隆(chlorsulfuron)、大克草(chlorthal)、草克樂(chlorthiamid)、乙基環醯草酯(cinidon-ethyl)、環庚草醚(cinmethylin)、西速隆(cinosulfuron)、落草胺(cisanilide)、剋草同(clethodim)、2-氯-3,5-二碘吡啶-4-基乙酸酯(cliodinate)、炔草酯(clodinafop)、2-[4-(4-氯苯氧基)苯氧基]丙酸(clofop)、可滅蹤(clomazone)、克普草(clomeprop)、果美生長素(cloprop)、氯丙殺草(cloproxydim)、畢克草(clopyralid)、氯酯磺草胺(cloransulam)、CMA、硫酸銅、CPMF、CPPC、必滅草(credazine)、甲酚、草隆(cumyluron)、氰草淨(cyanatryn)、氰乃淨(cyanazine)、環草敵(cycloate)、環磺隆(cyclosulfamuron)、環殺草(cycloxydim)、環莠隆(cycluron)、賽伏草(cyhalofop)、牧草快(cyperquat)、環丙津(cyprazine)、三環噻草胺(cyprazole)、環草胺(cypromid)、汰草龍(daimuron)、得拉本(dalapon)、邁隆(dazomet)、異丁草胺(delachlor)、甜菜安(desmedipham)、敵草淨(desmetryn)、二醛酯、汰克草(dicamba)、二氯苯腈(dichlobenil)、雙(三氯乙醛基)脲(dichloralurea)、苄胺靈(dichlormate)、2,4-滴丙酸
(dichlorprop)、2,4-滴丙酸-P(dichlorprop-P)、禾草靈(diclofop)、雙氯磺草胺(diclosulam)、1,1’-雙[2-(二乙氨基)-2-側氧乙基]-4,4’-聯吡啶(diethamquat)、乙醯甲草胺(diethatyl)、戊味禾草靈(difenopenten)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟草胺(diflufenican)、氟吡草腙(diflufenzopyr)、唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、愛落殺(dimethametryn)、汰草滅(dimethenamid)、汰草滅-P(dimethenamid-P)、草滅散(dimexano)、草噠酮(dimidazon)、撻乃安(dinitramine)、地樂特(dinofenate)、硝丙酚(dinoprop)、戊硝酚(dinosam)、達諾殺(dinoseb)、特樂酚(dinoterb)、大芬滅(diphenamid)、異丙凈(dipropetryn)、大刈特(diquat)、賽松(disul)、汰硫草(dithiopyr)、達有龍(diuron)、DMPA、DNOC、DSMA、EBEP、甘草津(eglinazine)、草多索(endothal)、三唑磺(epronaz)、EPTC、抑草蓬(erbon)、戊草丹(esprocarb)、乙丁烯氟靈(ethalfluralin)、胺苯磺隆(ethametsulfuron)、磺噻隆(ethidimuron)、硫草敵(ethiolate)、益覆滅(ethofumesate)、氯氟草醚(ethoxyfen)、亞速隆(ethoxysulfuron)、硝草酚(etinofen)、益尼普滅(etnipromid)、乙氧苯草胺(etobenzanid)、EXD、雙氧威(fenasulam)、2,4,5-涕丙酸(fenoprop)、芬殺草(fenoxaprop)、芬殺草-P、2,5-二氯-4-乙氧苄基4,5-二氫-5,5-二甲基-1,2-唑-3-基碸(fenoxasulfone)、2-(2,4,5-三氯苯氧基)乙醇(fenteracol)、噻唑禾草靈(fenthiaprop)、四唑醯草胺(fentrazamide)、非草隆(fenuron)、硫酸亞鐵、麥草氟酯
(flamprop)、麥草氟酯-M、伏速隆(flazasulfuron)、雙氟磺草胺(florasulam)、伏寄普(fluazifop)、伏寄普-P、異丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、貝殺寧(fluchloralin)、氟噻草胺(flufenacet)、2-(α,α,α-三氟-間甲苯氧基)煙醯苯胺(flufenican)、氟噠草酯(flufenpyr)、闊草清(flumetsulam)、氟每淨(flumezin)、氟烯草酸(flumiclorac)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、可奪草(fluometuron)、福泰芬(fluorodifen)、乙羧氟草醚(fluoroglycofen)、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、殺克丹(fluothiuron)、氟胺草唑(flupoxam)、氟異丙嘧草酯(flupropacil)、氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟氯比(fluroxypyr)、呋草酮(flurtamone)、氟噻草酯(fluthiacet)、氟磺胺草醚(fomesafen)、甲醯胺磺隆(foramsulfuron)、調節膦(fosamine)、呋氧草醚(furyloxyfen)、固殺草(glufosinate)、固殺草-P、嘉磷塞(glyphosate)、哈拉昔芬(halauxifen)、5-(2-氯-α,α,α,6-四氟-對甲苯氧基)-N-乙磺醯基-2-硝基苯甲醯胺(halosafen)、合速隆(halosulfuron)、氟啶草(haloxydine)、合氯氟(haloxyfop)、合氯氟-P、六氯丙酮、六氟鹽(hexaflurate)、菲殺淨(hexazinone)、咪草酸(imazamethabenz)、咪草啶酸(imazamox)、甲咪唑烟酸(imazapic)、依滅草(imazapyr)、滅草喹(imazaquin)、咪唑乙煙酸(imazethapyr)、依速隆(imazosulfuron)、茚草酮(indanofan)、N-[(1R,2S)-2,3-二氫
-2,6-二甲基-1H-茚-1-基]-6-[(1RS)-1-氟乙基]-1,3,5-三-2,4-二胺(indaziflam)、4-氰基-2,6-二碘苯基2-丙烯-1-基碳酸酯(iodobonil)、碘甲烷、碘甲磺隆(iodosulfuron)、碘苯腈(ioxynil)、抑草津(ipazine)、鹵苯胺唑(ipfencarbazone)、抑吡嘧丹(iprymidam)、草特靈(isocarbamid)、異草定(isocil)、丁草酮(isomethiozin)、異草完隆(isonoruron)、異丙林特(isopolinate)、異丙樂靈(isopropalin)、異丙隆(isoproturon)、愛速隆(isouron)、異草胺(isoxaben)、異氯草酮(isoxachlortole)、異唑草酮(isoxaflutole)、異草醚(isoxapyrifop)、特胺靈(karbutilate)、2-[(2,3-二氫-5,8-二甲基-1,1-二氧橋螺[4H-1-苯并噻喃-4,2’--[1,3]二烷]-6’-基)羰基]-1,3-環己二酮(ketospiradox)、乳氟禾草靈(lactofen)、環草定(lenacil)、理有龍(linuron)、MAA、MAMA、MCPA、脫禾草(MCPA-thioethyl)、MCPB、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸-P、地樂施(medinoterb)、滅芬草(mefenacet)、美福泰(mefluidide)、滅莠津(mesoprazine)、磺胺磺隆(mesosulfuron)、硝磺草酮(mesotrione)、斯美地(metam)、唑醯草胺(metamifop)、苯草酮(metamitron)、滅草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、二甲噠草伏(metflurazon)、甲基苯噻隆(methabenzthiazuron)、甲基丙樂靈(methalpropalin)、滅草唑(methazole)、甲殺丹(methiobencarb)、美西除靈(methiozolin)、滅草恆(methiuron)、醚草通(methometon)、格草净(methoprotryne)、溴甲烷、異硫氰酸甲酯、甲基殺草隆(methyldymron)、吡喃隆
(metobenzuron)、撲奪草(metobromuron)、莫多草(metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、滅必淨(metribuzin)、磺隆(metsulfuron)、稻得壯(molinate)、庚醯草胺(monalide)、莫尼速隆(monisouron)、單氯乙酸、綠谷龍(monolinuron)、滅草隆(monuron)、伐草快(morfamquat)、MSMA、萘普草(naproanilide)、滅落脫(napropamide)、納得爛(naptalam)、草不龍(neburon)、煙嘧磺隆(nicosulfuron)、吡氯草胺(nipyraclofen)、滅殺草(nitralin)、護谷(nitrofen)、三氟甲草醚(nitrofluorfen)、氟草敏(norflurazon)、草完隆(noruron)、OCH、坪草丹(orbencarb)、鄰二氯苯、嘧苯胺磺隆(orthosulfamuron)、歐拉靈(oryzalin)、丙炔草酮(oxadiargyl)、樂滅草(oxadiazon)、草噠松(oxapyrazon)、環氧嘧磺隆(oxasulfuron)、草酮(oxaziclomefone)、復祿芬(oxyfluorfen)、對氟隆(parafluron)、巴拉刈(paraquat)、克草猛(pebulate)、壬酸、施得圃(pendimethalin)、平速爛(penoxsulam)、五氟酚、甲氯醯草胺(pentanochlor)、環戊草酮(pentoxazone)、佈福松(perfluidone)、烯草胺(pethoxamid)、棉胺寧(phenisopham)、甜菜寧(phenmedipham)、乙基甜菜寧、p醯草隆(phenobenzuron)、苯基乙酸汞、畢克爛(picloram)、氟吡醯草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、亞砷酸鉀、疊氮化鉀、氰酸鉀、普拉草(pretilachlor)、氟嘧磺隆(primisulfuron)、環丙腈津(procyazine)、氨氟樂靈(prodiamine)、氟唑草胺(profluazol)、
環丙氟靈(profluralin)、氯苯噻草酮(profoxydim)、甘撲津(proglinazine)、撲滅通(prometon)、佈滅淨(prometryn)、雷蒙得(propachlor)、除草靈(propanil)、普拔草(propaquizafop)、普拔根(propazine)、苯胺靈(propham)、普樂寶(propisochlor)、丙苯磺隆(propoxycarbazone)、咪唑嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、甲硫磺樂靈(prosulfalin)、苄草丹(prosulfocarb)、三氟丙磺隆(prosulfuron)、撲滅生(proxan)、拔地草(prynachlor)、吡達農(pydanon)、雙唑草腈(pyraclonil)、派芬草(pyraflufen)、磺醯草吡唑(pyrasulfotole)、苄草唑(pyrazolynate)、百速隆(pyrazosulfuron)、匹唑芬(pyrazoxyfen)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、三氯吡啶醇(pyriclor)、噠草福(pyridafol)、必汰草(pyridate)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧啶硫蕃(pyrimisulfan)、嘧硫草醚(pyrithiobac)、吡唑碸(pyroxasulfone)、吡唑磺草胺(pyroxsulam)、快克草(quinclorac)、氯甲喹啉酸(quinmerac)、莫克草(quinoclamine)、克藻胺(quinonamid)、快伏草(quizalofop)、快伏草-P、硫氰苯胺(rhodethanil)、碸嘧磺隆(rimsulfuron)、嘧啶肟草醚(saflufenacil)、左旋莫多草(S-metolachlor)、另丁津(sebuthylazine)、仲丁通(secbumeton)、西殺草(sethoxydim)、環草隆(siduron)、草滅淨(simazine)、西瑪通(simeton)、西草淨(simetryn)、SMA、亞砷酸鈉、疊氮化鈉、氯酸鈉、磺草酮(sulcotrione)、草克死(sulfallate)、氟磺唑草胺(sulfentrazone)、嘧磺隆(sulfometuron)、磺醯磺
隆(sulfosulfuron)、硫酸、氮雜環庚-1-基羰基甲基胺磺酸甲酯(sulglycapin)、滅草靈(swep)、TCA、牧草胺(tebutam)、得匍隆(tebuthiuron)、四氫呋喃甲基三酮(tefuryltrione)、田寶三酮(tembotrione)、得殺草(tepraloxydim)、特草定(terbacil)、特草靈(terbucarb)、特丁草胺(terbuchlor)、特丁通(terbumeton)、草凈津(terbuthylazine)、特丁淨(terbutryn)、四氟隆(tetrafluron)、欣克草(thenylchlor)、噻氟隆(thiazafluron)、噻草啶(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、甲基酮脲磺草吩酯(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、殺丹(thiobencarb)、仲草丹(tiocarbazil)、6-氯-5-(甲基硫代基)嘧啶-2,4-二胺(tioclorim)、吡草磺(topramezone)、三甲苯草酮(tralkoxydim)、2’-[(4,6-二甲氧基-1,3,5-三-2-基)羰基]-1,1,6’-三氟-N-甲基甲磺醯苯胺(triafamone)、燕麥畏(tri-allate)、、醚苯磺隆(triasulfuron)、三氟草胺(triaziflam)、苯磺隆(tribenuron)、殺草畏(tricamba)、三氯比(triclopyr)、三地芬(tridiphane)、草達津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三福林(trifluralin)、氟胺磺隆(triflusulfuron)、2-[4-[4-(三氟甲基)苯氧基]苯氧基]丙酸(trifop)、丙酮(R)-O-{2-[4-(α,α,α-三氟-對甲苯氧基)苯氧基]丙醯基}肟(trifopsime)、三羥基三、三甲隆(trimeturon)、1-(6-異丙基-1,1,4-三甲基二氫茚-5-基)丙-1-酮(tripropindan)、草達克(tritac)、三氟甲磺隆(tritosulfuron)、萬隆(vernolate),及二甲苯草胺(xylachlor)。
本揭露之另一實施例係一種用於控制或預防真菌攻擊之方法。此方法包含對土壤、植物、根部、葉子,或真菌所在地,或預防侵害之所在地(例如,施用至穀類或葡萄植物)施用一殺真菌有效量之一或多種具化學式I之化合物。此等化合物係適合以殺真菌量處理各種植物,同時展現低植物毒性。此等化合物可以保護劑及/或噴灑滅蟲劑之方式使用。
此等化合物已被發現具有顯著殺真菌效果,特別是對於農業用途。許多此等化合物係特別有效地與農業作物及園藝植物使用。
熟習此項技藝者會瞭解此化合物對於前述真菌之功效建立此等化合物作為殺真菌劑之普遍用途。
此等化合物具有對抗真菌病原體之廣範圍活性。例示之病原體可不受限地包含小麥葉斑病(禾生球腔菌(Mycosphaerella graminicola);無性態:枯葉病菌(Zymoseptoria tritici))、小麥葉锈病(小麥葉锈菌(Puccinia triticina))、小麥條銹病(條形扁菌(Puccinia striiformis))、蘋果結痂(蘋果黑星菌(Venturia inaequalis))、葡萄藤白粉病(葡萄白粉病菌(Uncinula necator))、大麥雲紋病(大麥雲紋病菌(Rhynchosporium secalis))、稻瘟病(稻熱病菌(Magnaporthe grisea))、大豆銹病(豆薯層銹菌(Phakopsora pachyrhizi))、小麥稃枯病(子囊菌(Leptosphaeria nodorum))、小麥白粉病(小麥白粉菌(Blumeria graminis f.sp.tritici))、大麥白粉病(大麥白粉菌(Blumeria graminis f.sp.hordei))、瓜類白粉病
(二孢白粉菌(Erysiphe cichoracearum))、瓜類炭疽病(胡瓜炭疽病菌(Glomerella lagenarium))、甜菜葉斑(甜菜生尾孢菌(Cercospora beticola))、蕃茄早枯萎病(索蘭尼鏈格孢(Alternaria solani)),及大麥斑枯(禾旋孢腔菌(Cochliobolus sativus))之致病原。被施用之活性材料的準確量不僅依欲被施用之特定活性物質而定,而且亦依所欲之特定作用、欲被控制之真菌物種及其生長階段,與欲與此化合物接觸之植物或其它產物之部份而定。所有此等化合物及含有此等化合物之調配物於相似濃度或對抗相同真菌物種可能非相等功效。
此等化合物係以抑制疾病及植物學可接受之量有效地與植物使用。術語"抑制疾病及植物學可接受之量"係指殺死或抑制欲控制之植物疾病但對植物無顯著毒性之化合物量。此量一般會係從約0.1至約1000ppm(每百萬之份數),且1至500ppm係較佳。所需之化合物準確濃度係隨欲被控制之真菌疾病、使用之調配物型式、施用方法、特別植物物種、氣候條件等而改變。一適合施用率典型上係從約0.10至約4磅/英畝(約0.01至0.45克/平方公尺,g/m2)之範圍。
如瞭解此處教示之熟習此項技藝者所顯知般,此處提供之任何範圍或所欲值可於未損失尋求之功效下擴大或改變。
具化學式I之化合物可使用已知化學程序製造。於此揭露中未特別提及之中間物係可購得,可藉由於化學
文獻中揭露之路徑製造,或可自商業上之起始材料利用標準程序輕易合成。
下列流程係例示產生具化學式(I)之吡啶醯胺化合物之方式。下列說明及範例係提供作為例示目的,且不應被闡釋作為以取代基或取代式樣而言之限制。
具化學式1.5之化合物可如流程1,步驟a-e概述般製備。具化學式1.1之嗎啉醯胺可如a所述般藉由使具化學式1.0之化合物及嗎啉於約95℃之高溫加熱而製備。如b所示般,具化學式1.1之化合物可於從約0℃至約22℃之溫度,於如N,N-二甲基甲醯胺(DMF)之一極性非質子性溶劑中,以諸如氫化鈉(NaH)一鹼處理,及4-甲氧基苯甲氯處理,以提供具化學式1.2之化合物。如c所示般,具化學式1.2之化合物可於如四氫呋喃(THF)之一極性非質子性溶劑中,於約0℃之降溫,以諸如1-丙烯基溴化鎂之一格里那(Grignard)試劑處理,提供具化學式1.3之化合物。如d所示般,具化學式1.3之化合物可以於如THF中之一極性非質子性溶劑中之一溶液於從約0℃至約22℃之溫度,添加至於二乙醚(Et2O)中之自氯化鋅(ZnCl2)及硼氫化鈉(NaBH4)製備之硼氫化鋅之一溶液,提供具化學式1.4之化合物。如e所示,具化學式1.4之化合物可於從約0℃至約22℃之溫度於如DMF之一極性非質子性溶劑中以諸如NaH之一鹼,及諸如苯甲基溴之一苯甲基鹵處理,提供具化學式1.5之化合物。
具化學式2.1之化合物可使用流程2,步驟a-b中概述之方法獲得。如a所示,具化學式1.5之化合物可接受臭氧化條件,諸如,於約-78℃之溫度,於諸如二氯甲烷(DCM)及甲醇(MeOH)之一溶劑混合物中,以臭氧(O3)處理,然後,以諸如NaBH4之一還原劑抑制,提供具化學式2.0之化合物。如b所示般,具化學式2.1之化合物可藉由於從約0℃至約22℃之溫度,於如DMF之一極性非質子性溶劑中,以諸如NaH之一鹼及諸如烯丙基溴之一烯丙基鹵)處理具化學式2.0之醇獲得。
具化學式3.3之化合物(其中,R8係如原來定義般)
可藉由流程3,步驟a-b所示之方法製備。如a所示般,具化學式3.1之化合物(其中,R8係如原始定義般,且R9係烷基或烷氧基)可自具化學式3.0之化合物(其中,R8係如原始定義般),於諸如甲苯之一溶劑中且於約0℃至22℃之溫度,如Ely,R.J.;Morken,J.P.J.Am.Chem.Soc.2010,132,2534-2535所述般,於諸如雙(環辛二烯)鎳(0)(Ni(cod)2)之一鎳催化劑存在中,以諸如頻哪醇硼烷之-烷氧基硼烷處理而製備。如b所示般,具化學式3.3之化合物(其中,R8係先前定義般)可自具化學式3.1之化合物(其中,R8及R9係如前定義)藉由以個別如Cheng,C.;Brookhart,M.Angew.Chem.Int.Ed.2012,51,9422-9424及Takai,K.;Heathcock,C.H.J.Org.Chem.1985,50,3247-3251所述般製備及特徵化之一自以苯甲基(Bn)保護之乳酸酯衍生之醛(諸如,具化學式3.2之化合物)處理而製備。
具化學式4.3之化合物(其中,R2係如原始般定義,但不是氫)可依據流程4,步驟a-c所示之方法製備。如a所示般,具化學式3.3之化合物(其中,R2係如原始定義般,但不是氫)可於諸如DMF及水(H2O)之一溶劑混合物中,於一氧(O2)氛圍下,於約65℃之高度,以諸如二氯鉑(PdCl2)之
一鈀催化劑,及諸如氯化銅(CuCl)之一銅鹽處理,提供具化學式4.0之化合物(其中,R2係如原始定義般,但不是氫)。如b所示般,具化學式4.1及4.2之化合物的一不合邏輯混合物(其中,R2係如原始般定義,但不是氫)可藉由於諸如DCM之一鹵化溶劑中,於從約-15℃至約-10℃之964D降溫,以過氧雙(三甲基矽烷)及三氟甲烷磺酸三甲基矽烷酯處理具化學式4.0之化合物(其中,R2係如前定義般)而獲得。如c所述般,具化學式4.1及4.2之化合物的一混合物(其中,R2係如前定義般)可於諸如含水MeOH之一溶劑混合物中以諸如碳酸鉀(K2CO3)之一鹼處理,提供具化學式4.3之二醇(其中,R2係如前定義般)。
具化學式5.1之化合物(其中,R2係如原始定義般,但不是氫),及具化學式5.2之化合物(其中,R1係烷基,且R2係如原始定義般,但不是氫)可依據流程5,步驟a-c所示之方法製備。如於a所述及由Lee,D.;Williamson,C.L.;
Chan,L.;Taylor,M.S.J.Am.Chem.Soc.2012,134,8260-8267所述般,具化學式4.2之化合物(其中,R2係如原始定義般,但不是氫)可於諸如2,2-二苯基-1,3,2-唑硼烷-3-鎓-2-鹽之一催化劑存在中,於如乙腈(CH3CN)之一極性非質子性溶劑中,於約60℃之高溫,以諸如烯丙基溴之一烯丙基鹵、碘化鉀(KI),及諸如碳酸鉀(K2CO3)之一鹼處理,提供具化學式5.0之化合物(其中,R2係如原始定義般,但不是氫)。如b所示般,具化學式5.1之化合物(其中,R2係如前定義般)可藉由於如DCM之一鹵化溶劑中,以三氟甲烷磺酸三異丙基矽烷酯及諸如2,6-二甲基吡啶之一胺鹼處理具化學式5.0之化合物(其中,R2係如前定義般)製備。另外,如c所示般,具化學式5.2之化合物(其中,R1及R2係如前定義般)可藉由於如THF或DMF之一極性非質子性溶劑中,於從約22℃至約40℃之溫度,以諸如第三丁氧化鉀之一鹼及如(溴甲基)環丙烷之一烷基鹵處理具化學式5.0之化合物(其中,R2係如前定義般)而製備。
具化學式6.3之化合物(其中,R2係如原始定義般)可藉由流程6,步驟a-c概述之方法獲得。如a所示般,具化學式6.0之化合物(其中,R2係如原始定義般)可於諸如DCM及MeOH之一溶劑混合物中,於約-78℃之降溫,以O3處理,其後以諸如三苯基膦(PPh3)之一還原劑抑制,提供具化學式6.1之醛(其中,R2係如原始定義般)。如b所示般,具化學式6.1之化合物(其中,R2係如前定義般)可於如DCM之一鹵化溶劑中,諸如2-((第三丁氧基羰基)胺基)-2-(二甲氧基膦基)乙酸甲酯之一葉立德(ylide)先質,及諸如1,8-二氮雜二環[5.4.0]十一-7-烯(DBU)一鹼處理,提供具化學式6.2之化合物(其中,R2係如原始定義般)。如c所示般,具化學式6.2之化合物(其中,R2係如前定義般)可於氫氣(H2)存在中,以諸如(+)-三氟甲烷磺酸1,2-雙((2S,5S)-2,5-二乙基磷雜環戊烷
基)苯(1,5-環辛二烯)銠(I)((S,S)-Et-DuPhos-Rh)之一對掌性催化劑處理,提供具化學式6.3之化合物(其中,R2係如前定義般)。
具化學式7.2之化合物(其中,R2係如原始定義般,但不是氫)可如流程7,步驟a-b概述般製備。如a所描述般,於諸如含水THF之一溶劑混合物中,以諸如氫氧化鋰單水合物(LiOH.H2O)之一氫氧化物鹼處理具化學式7.0之化合物(其中,R2係原始定義般,但不是氫)提供具化學式7.1之化合物(其中,R2係如原始定義般,但不是氫)。如b所示般,於H2存在中,於諸如乙酸乙酯(EtOAc)之一溶劑中,以諸如於碳上之鈀(Pd/C)之一催化劑處理具化學式7.1之化合物(其中,R2係如前定義般)提供具化學式7.2之化合物(其中,R2係如前定義般)。
具化學式8.2之化合物可如流程8,步驟a-b描述般自化學式8.0之化合物獲得。如a所示般,化學式8.1之化合物可自化學式8.0之具化合物,藉由於如含水DCM之一溶劑混合物中,以諸如2,3-二氯-5,6-二氰基-對-苯醌(DDQ)之一氧化物處理而獲得。如b所述般,於諸如含水THF之一溶劑混合物中,以諸如LiOH.H2O之一氫氧化物鹼處理具化學式8.1之化合物提供具化學式8.2之化合物。
具化學式9.1之化合物(其中,R2係如原始定義般)可依據流程9概述之方法製備。如a所示般,具化學式9.1之化合物(其中,R2係如前定義般)可自具化學式9.0之化合物(其中,R2係如原始定義般),藉由於4-12小時(h)期間,
使於諸如DCM之一鹵化溶劑或諸如甲苯之一芳香族溶劑中之具化學式9.0之化合物的一溶液添加至於如DCM之一鹵化溶劑或如甲苯之一芳香族溶劑中之諸如4-二甲基胺基吡啶(DMAP)之一鹼及諸如2-甲基-6-硝基苯甲酸酐(MNBA)之一混合酐的一混合物而獲得。
具化學式10.1之化合物(其中,R2係如原始定義般,但不是氫)可依據流程10概述之方法製備。如a所示般,具化學式10.1之化合物(其中,R2係如前定義般)可自具化學式10.0之化合物(其中,R2係如原始定義般,但不是氫)藉由於如THF之一極性非質子性溶劑中,於約0℃之降溫,曝置於諸如四-N-丁基氟銨(TBAF)之一氟化物來源而獲得。
具化學式11.1之化合物可依據流程11概述之方法製備。如a所示般,具化學式11.0之化合物可於H2存在中,於諸如EtOAc之一溶劑中以諸如Pd/C之一催化劑處理提供具化學式11.1之化合物。
具化學式12.1,12.2,12.3,及12.4之化合物(其中,R1及R2係如原始定義般)可使用流程12,步驟a-d概述般之方法獲得。如a所示般,具化學式12.1之化合物(其中,R1係醯基,且R2係如前定義般)可自具化學式12.0之化合物(其中,R2係如原始定義般)藉由於諸如三乙胺(NEt3)之一鹼及諸如DMAP之一胺催化劑存在中,於如DCM之一鹵化溶劑中,以諸如異丁醯基氯之一醯基氯處理而製製備。另外,如b所示般,具化學式12.2之化合物(其中,R1係芳基,且R2係如前定義般)可自具化學式12.0之化合物(其中,R2係如前定義般),藉由於諸如乙酸銅(II)(Cu(OAc)2)之一催化劑存
在中,於如甲苯之一芳香族烴溶劑中,於約50℃之高溫,以諸如雙(乙酸根-O)三苯基鉍(V)(Bi(OAc)2Ph3)之一有機金屬物種處理製備。具化學式12.3之化合物(其中,R1係烯基,且R2係如原始定義般)可自具化學式12.0之化合物(其中,R2係如前定義般),藉由於諸如三(二亞苯甲基丙酮)-二鈀(0)(Pd2(dba)3)之一催化劑,及諸如1,1'-雙(二苯基膦基)芴(dppf)之一配位體存在中,於如THF或甲苯之一非質子性溶劑中,於約60℃之高溫,以諸如第三丁基(2-甲基烯丙基)碳酸酯之一烯丙基碳酸酯處理而製備。另外,如d所示般,具化學式12.4之化合物(其中,R1係烷基,且R2係如前定義般)可於H2存在中,於如EtOAc之溶劑中,以具化學式12.3之化合物(其中,R1及R2係如前定義般)以諸如Pd/C之一催化劑處理而製備。
具化學式13.3之化合物(其中,R1及R2係如原始定義般,但R1不是矽烷基或氫)可經由流程13,步驟a-d所示之方法製備。如a所述般,具化學式13.0之化合物(其中,R1及R2係如原始定義般,但R1不是烯基、矽烷基,或氫)可於如DCM之一鹵化溶劑中,諸如於二烷中之氯化氫(HCl)之4N溶液的一酸處理而提供具化學式13.1之化合物(其中,R1及R2係如原始定義般,但R1不是烯基、矽烷基,或氫)。形成之氫氯酸鹽於使用前可被中和化產生游離胺,或於步驟b於原位中和化。如於b所示,具化學式13.3之化合物(其中,R1及R2係如原始定義般,但R1不是烯基、矽烷基,或氫)可自具化學式13.1之化合物(其中,R1及R2係如前定義般),藉由於諸如二異丙基乙胺之一鹼,及諸如苯并三唑-1-基-氧三吡咯啶基鏻六氟磷酸鹽(PyBOP)或O-(7-氮雜苯并三唑-1-基)-N,N,N',N'-四甲基脲鎓六氟磷酸鹽(HATU)之一肽偶合劑存在中,於如DCM之一鹵化溶劑中,以3-羥基-4-甲氧基吡啶甲酸處理而製備。另外,如c所描述,具化學式13.0之化合物(其中,R1係烯基,且R2係如原始定義般)可於如DCM之一鹵化溶劑中以三氟甲烷磺酸三甲基矽烷酯及諸如2,6-二甲基吡啶之一鹼處理,其後以諸如MeOH之一醇處理,提供具化學式13.2之化合物(其中,R1係烯基,且R2係如原始定義般)。如d所示般,具化學式13.3之化合物(其中,R1係烯基,且R2係如原始定義般)可自具化學式13.2之化合物(其中,R1及R2係如前定義般),藉由於諸如二異丙基乙胺之
一鹼,及諸如PyBOP或HATU之一肽偶合劑存在中,於如DCM之一鹵化溶劑中,以3-羥基-4-甲氧基吡啶甲酸處理而製備。
具化學式14.0之化合物(其中,R1、R2,及R4係如原始定義般,但R1不是矽烷基或氫)可依據流程14概述之方法製備。具化學式14.0之化合物(其中,R1、R2,及R4係如前定義般)可自具化學式13.3之化合物(其中,R1及R2係如原始定義般,但R1不是矽烷基或氫),藉由於如丙酮之一溶劑中,以一適當烷基鹵,且具有或不具有諸如碘化鈉(NaI)之試劑及諸如碳酸鈉(Na2CO3)或碳酸鉀(K2CO3)之一鹼碳酸鹽而處理,或藉由於諸如吡啶、NEt3、DMAP,或此等之混合物的一胺鹼存在中,於諸如DCM之一非質子性溶劑中,以一醯基鹵處理而製備。
範例1,步驟1:製備(S)-2-羥基-1-嗎啉基丙-1-酮:
(S)-2-羥基丙酸乙酯(10.0克(g),85.0毫莫耳(mmol))及嗎啉(15.1毫升(mL),174毫莫耳)之一溶液於95℃攪拌72小時(h)。反應混合物冷卻至室溫,且過量之嗎啉於減壓(1托耳,50℃)下蒸發。形成之粗製殘餘物藉由急速管柱層析術純化(矽石凝膠(SiO2),於己烷內0→90%丙酮)提供標題化合物(12.0克,89%),呈黃色油:1H NMR(400MHz,CDCl3)δ 4.44(dq,J=7.4,6.7Hz,1H),3.81-3.58(m,7H),3.46-3.38(m,2H),1.33(d,J=6.6Hz,3H);ESIMS m/z 160([M+H]+)。
範例1,步驟2:製備(S)-2-((4-甲氧基苯甲基)氧)-1-嗎啉基丙-1-酮*:
於四氫呋喃(THF;26毫升)中之(S)-2-羥基-1-嗎啉基丙-1-酮(8.00克,50.3毫莫耳)之溶液於0℃添加至於N,N-二甲基甲醯胺(DMF;100毫升)中之氫化鈉(NaH;3.02克,75毫莫耳,於礦物油中之60%分散液)之懸浮液。於0℃攪拌5分鐘(min)後,緩慢添加淨1-(氯甲基)-4-甲氧基苯(8.18毫升,60.3毫莫耳)。反應混合物自冷浴移除,且於室溫攪拌5小時。反應混合物以1/2飽和(sat.)含水(aq.)氯化銨(NH4Cl;100毫升)抑制,且以二乙基醚(Et2O;100毫升)稀釋。此等相被分離,且水相以Et2O(2x100毫升)萃取,且混合之有機相以飽和含水氯化鈉(NaCl,鹽水;50毫升)清洗,於硫酸鈉(Na2SO4)上乾燥,過濾,及蒸發。形成之粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→60%丙酮)提供標題化合物(9.85克,70%),呈無色油:1H NMR(500MHz,CDCl3)δ 7.28-7.21(m,2H),6.92-6.85(m,2H),4.52(d,J=11.2Hz,1H),4.41(d,J=11.3Hz,1H),4.30(q,J=6.8Hz,1H),3.81(s,3H),3.73-3.56(m,8H),1.43(d,J=6.8Hz,3H);13C NMR(126MHz,CDCl3)δ 170.68,159.43,129.60,129.46,113.88,75.11,70.89,67.06,66.80,55.30,45.64,42.50,17.84;ESIMS m/z 280([M+H]+)。*參考資料:Nogawa,M.;Sugawara,S.;Iizuka,R.;Shimojo,M.;Ohta,H.;Hatanaka,
M.;Matsumoto,K.Tetrahedron 2006,62,12071-12083。
範例1,步驟3:製備(S)-2-((4-甲氧基苯甲基)氧)己-4-烯-3-酮:
對於THF(36毫升)中之(S)-2-((4-甲氧基苯甲基)氧)-1-嗎啉基丙-1-酮(5.00克,17.9毫莫耳)之溶液於15分鐘期間,於0℃,以滴液方式添加丙-1-烯-1-基溴化鎂(53.6毫升,26.8毫莫耳,於THF中,0.5莫耳(M))。形成之混合物於0℃攪拌4小時,然後,倒至一充分攪拌之0℃的1M硫酸氫鈉(NaHSO4;100毫升)溶液。混合物於水(H2O;25毫升)與Et2O(75毫升)間分配,且相被分離。水相以Et2O(2x75毫升)萃取,且混合之有機相以鹽水(30毫升)清洗,於Na2SO4上乾燥,過濾,及蒸發。粗製殘餘物藉由急速管柱層析術純化(SiO2,己烷中0→25%丙酮)提供標題化合物之E及Z烯酮之約1:1混合物(3.45克,82%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.30-7.22(m,4H),7.06(dq,J=15.6,6.9Hz,1H),6.92-6.84(m,4H),6.59-6.48(m,2H),6.38(dq,J=11.5,7.2Hz,1H),4.50(dd,J=11.2,3.1Hz,2H),4.37(dd,J=11.2,4.9Hz,2H),4.02(q,J=6.9Hz,1H),3.91(q,J=6.9Hz,1H),3.83-3.78(m,6H),2.17(dd,J=7.2,1.7Hz,3H),1.92(dd,J=6.9,1.7Hz,3H),1.34(d,J=4.6Hz,3H),1.32(d,J=4.6Hz,
3H);13C NMR(101MHz,CDCl3)δ 203.45,201.26,159.38,159.36,146.04,144.53,129.81,129.75,129.56,129.53,126.12,122.89,113.86,80.81,79.70,71.51,71.46,55.29,18.54,18.00,17.82,1624;ESIMS m/z 257([M+Na]+)。
範例1,步驟4:製備(2S,3R)-2-((4-甲氧基苯甲基)氧)己-4-烯-3-醇*:
對於Et2O(29毫升)中之硼氫化鈉(NaBH4;1.32克,34.8毫莫耳)之溶液,於15分鐘期間,於0℃,添加氯化鋅(II)(ZnCl2;18.1毫升,18.1毫莫耳,於Et2O,1M),且於冰熔融時,使反應混合物加溫至室溫隔夜。形成之硼氫化鋅(Zn(BH4)2)溶液冷卻至0℃,且於15分鐘期間,經由套管式轉移以於THF(29毫升)中之(S)-2-((4-甲氧基苯甲基)氧)己-4-烯-3-酮(3.4克,14.5毫莫耳)之溶液處理(以4毫升THF沖洗)。反應混合物於0℃攪拌2小時,自冷浴移除,然後,於室溫攪拌30分鐘。反應混合物以Et2O(50毫升)稀釋,且藉由依序添加1/2飽和含水NH4Cl(40毫升)及H2O(40毫升)小心抑制。相被分離,且水相以Et2O(2x50毫升)萃取。混合之有機相以鹽水(25毫升)清洗,於Na2SO4上乾燥,過濾,及蒸發。粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→30%丙酮),提供具有10:1之非鏡像異構物比率的標題化合物之E及Z烯烴異構物之約1:1混合物(2.95克,86%),呈
無色油:1H NMR(400MHz,CDCl3)主要醇非鏡像異構物δ 7.31-7.23(m,2H),6.93-6.84(m,2H),5.79-5.58(m,1H),5.54-5.38(m,1H),4.66-4.51(m,1.5H),4.50-4.42(m,1H),4.19-4.08(m,0.5H),3.80(app s,3H),3.63-3.50(m,1H),2.18(s,1H),1.75-1.62(m,3H),1.17-1.09(m,3H);13C NMR(101MHz,CDCl3)δ 159.21,130.61,130.59,129.43,129.24,129.22,129.09,128.61,127.54,113.83,77.16,74.55,70.53,70.51,69.30,55.28,17.88,14.18,14.15,13.49;ESIMS m/z 236([M]+)。*參考資料:Ichikawa,Y.;Egawa,H.;Ito,T.;Isobe,M.;Nakano,K.;Kotsuki,H.Org.Lett.2006,8,5737-5740。
範例1,步驟5:製備1-((((2S,3R)-3-(苯甲氧基)己-4-烯-2-基)氧)甲基)-4-甲氧基苯:
對於DMF(28毫升)中之(2S,3R)-2-((4-甲氧基苯甲基)氧)己-4-烯-3-醇(2.95克,12.5毫莫耳)的溶液,於0℃添加NaH(0.749克,18.7毫莫耳,於礦物油中之60%分散液)。反應混合物於0℃攪拌10分鐘,然後,以淨苯甲基溴(1.78毫升,15.0毫莫耳)處理。反應混合物於0℃攪拌4小時,加溫至室溫並且攪拌1小時,以1/2飽和含水NH4Cl(40毫升)抑制,且以Et2O(50毫升)稀釋。相被分離,且水相以Et2O(2 x 50毫升)萃取。混合之有機相以鹽水(25毫升)清洗,於Na2SO4
上乾燥,過濾,及蒸發。粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷內之0→30% EtOAc)提供標題化合物之E及Z烯烴異構物的約1:1混合物(4.0克,88%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.35-7.22(m,7H),6.89-6.81(m,2H),5.81(dqd,J=11.1,6.9,1.1Hz,0.5H),5.69(dqd,J=15.5,6.4,0.8Hz,0.5H),5.53-5.41(m,1H),4.67-4.58(m,1H),4.57-4.51(m,2H),4.44-4.34(m,1H),4.17(ddd,J=9.3,4.2,1.1Hz,0.5H),3.82-3.76(m,3H),3.74-3.66(m,0.5H),3.65-3.54(m,1H),1.80-1.73(m,1.5H),1.61(dd,J=7.0,1.8Hz,1.5H),1.22-1.14(m,3H);13C NMR(101MHz,CDCl3)δ 159.00,158.98,139.00,138.96,131.19,131.17,130.51,129.23,129.16,128.71,128.57,128.23,127.66,127.58,127.31,127.25,113.64,83.17,76.84,76.64,71.06,71.04,69.97,55.28,17.94,16.47,16.31,13.62;ESIMS m/z 349([M+Na]+)。
範例2,步驟1:製備(2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁-1-醇:
對於二氯甲烷(DCM;28毫升)及甲醇(MeOH;2.8毫升)中之1-((((2S,3R)-3-(苯甲氧基)己-4-烯-2-基)氧)甲基)-4-甲氧基-苯(4.0克,12.3毫莫耳)的溶液,添加於DCM中之1-((E)-(4-((E)-苯基二氮烯基)苯基)二氮烯基)-萘-2-醇
(Sudan III指示劑;75微升(μL))的0.1%溶液。反應混合物冷卻至-78℃(乾冰/丙酮),且燒瓶與一臭氧產生器連接。臭氧(O3)起泡通過此溶液至此溶液變無色為止(~30分鐘)。然後,氧氣(O2)起泡通過此溶液5分鐘,且此溶液以MeOH(6毫升)及NaBH4(1.39克,36.8毫莫耳)處理。燒瓶自冷浴移除,且使反應混合物緩慢加溫至室溫隔夜。反應混合物以1/2飽和含水NH4Cl(40毫升)抑制,且以DCM(40毫升)及H2O(20毫升)稀釋,相被分離,且水相以DCM(2x40毫升)萃取。混合之有機相以鹽水(15毫升)清洗,藉由通過一相分離器匣而乾燥,並且蒸發。形成之粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→15%丙酮)提供標題化合物(3.18克,82%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.37-7.21(m,7H),6.91-6.82(m,2H),4.63(d,J=1.3Hz,2H),4.57(d,J=11.3Hz,1H),4.45(d,J=11.3Hz,1H),3.82-3.65(m,6H),3.42(dt,J=5.7,4.6Hz,1H),2.33(t,J=6.2Hz,1H),1.26(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ 159.25,138.24,130.39,129.37,128.47,127.90,127.81,113.87,82.13,75.26,72.45,70.93,61.80,55.29,16.51;ESIMS m/z 339([M+Na]+)。
範例2,步驟2:製備1-((((2S,3R)-4-(烯丙氧基)-3-(苯甲氧基)丁-2-基)氧)甲基)-4-甲氧基苯:
對於DMF(25毫升)中之(2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁-1-醇(3.18克,10.1毫莫耳)的溶液,於0℃添加NaH(0.603克,15.1毫莫耳,於礦物油中之60%分散液)。反應混合物於0℃攪拌10分鐘,且以淨烯丙基溴(0.870毫升,10.1毫莫耳)處理。於0℃經3小時後,反應混合物自冷浴移除,另外攪拌1小時,以1/2飽和含水NH4Cl(40毫升)抑制,且以Et2O(50毫升)稀釋。相被分離,且水相以Et2O(2x50毫升)萃取。混合之有機相以鹽水(25毫升)清洗,於Na2SO4上乾燥,過濾,及蒸發。形成之粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→20% EtOAc)提供標題化合物(3.14克,79%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.40-7.28(m,4H),7.30-7.20(m,3H),6.90-6.81(m,2H),5.90(ddt,J=17.3,10.3,5.5Hz,1H),5.27(dq,J=17.2,1.7Hz,1H),5.21-5.13(m,1H),4.74(d,J=11.8Hz,1H),4.66(d,J=11.8Hz,1H),4.53(d,J=11.4Hz,1H),4.45(d,J=11.4Hz,1H),4.02-3.95(m,2H),3.79(s,3H),3.73-3.54(m,4H),1.23(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ 159.09,138.86,134.90,130.90,129.22,128.25,127.83,127.44,116.76,113.73,80.92,74.70,72.75,72.28,70.81,70.21,55.28,16.00;ESIMS m/z 380([M+Na]+)。
範例3:製備(2S,3R,4S)-4-苯甲基-2-(苯甲氧基)己-5-烯-3-醇:
對一圓底燒瓶,於一惰性氛圍(N2手套袋)下,添加雙(環辛二烯)鎳(0)(Ni(cod)2;0.168克,0.609毫莫耳)及三環己基膦(P(C6H11)3;0.213克,0.761毫莫耳),且燒瓶被封蓋且自袋子移除。混合物以甲苯(22毫升)稀釋,且於室溫添加4,4,5,5-四甲基-1,3,2-二硼烷(6.63毫升,45.7毫莫耳)。反應混合物於一冰浴中冷卻至0℃,且於10分鐘期間以滴液方式以淨(E)-丁-1,3-二烯-1-基苯(4.76克,36.5毫莫耳)處理。混合物自冰浴移除,且於室溫攪拌2小時,於一乾冰/丙酮浴中冷卻至-78℃,且以(S)-2-(苯甲氧基)丙醛(5克,30.5毫莫耳)處理,其後,以三氟化硼二乙醚(BF3.OEt2;0.376毫升,3.05毫莫耳)處理。使反應混合物緩慢加溫至室溫隔夜,且以MeOH(5毫升)處理抑制。攪拌30分鐘後,反應混合物被濃縮,且藉由急速管柱層析術純化(SiO2,於己烷中0→50% EtOAc)提供標題化合物(8.95克,99%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.39-7.30(m,3H),7.32-7.25(m,1H),7.25-7.21(m,2H),7.20-7.11(m,4H),5.45(ddd,J=17.2,10.3,9.5Hz,1H),4.93(dd,J=10.3,1.8Hz,1H),4.79(ddd,J=17.2,1.9,0.7Hz,1H),4.55(d,J=11.7Hz,1H),4.46(d,J=11.7Hz,1H),3.76(ddd,J=9.2,3.2,2.2Hz,1H),3.56(qd,J=6.3,3.1Hz,1H),3.19(dd,J=13.3,3.5Hz,1H),2.58(dd,
J=13.4,9.3Hz,1H),2.39(dt,J=9.2,3.4Hz,1H),2.37(d,J=2.3Hz,1H),1.17(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ 139.92,138.48,137.37,129.81,128.46,127.94,127.70,127.66,125.76,117.21,76.22,73.78,70.56,48.44,37.63,12.21;ESIMS m/z 319([M+Na]+)。
範例4,步驟1:製備(3R,4R,5S)-5-(苯甲氧基)-3-(4-氟苯甲基)-4-羥基己-2-酮:
於DMF(13.2毫升)及水(2.6毫升)中之(2S,3R,4S)-2-(苯甲氧基)-4-(4-氟苯甲基)己-5-烯-3-醇(1克,3.18毫莫耳)之一溶液以O2噴射5分鐘,然後,以氯化鈀(II)(PdCl2;0.141克,0.795毫莫耳)及氯化銅(I)(CuCl;0.630克,6.36毫莫耳)處理。溶液加熱至65℃,且於一靜態O2氛圍下劇烈攪拌隔夜。反應混合物以Et2O(10毫升)稀釋,且通過塞理塑料(Celite®)過濾。濾液以另外之Et2O(20毫升)稀釋,且以飽和含水NH4Cl清洗。相被分離,且水相以Et2O(10毫升)萃取。混合之有機相依序以1當量(N)含水氯化氫(HCl;20毫升)及飽和含水碳酸氫鈉(NaHCO3;20毫升)清洗,於MgSO4上乾燥,及過濾。溶劑被蒸發,且粗製油藉由正相及逆相急速管柱層析術純化(SiO2,於己烷中1→40%丙酮,其後係C18,於H2O中10→100%乙腈(CH3CN))提供標題化合
物(116.4毫克,11%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.40-7.28(m,5H),7.08-7.01(m,2H),6.93(t,J=8.7Hz,1H),4.61(d,J=11.5Hz,1H),4.39(d,J=11.5Hz,1H),3.87(td,J=5.9,2.1Hz,1H),3.49(p,J=6.1Hz,1H),3.15(ddd,J=10.1,5.5,4.2Hz,1H),3.01(dd,J=13.7,4.2Hz,1H),2.86-2.80(m,2H),2.79(s,1H),1.81(s,3H),1.28(d,J=6.1Hz,3H);19F NMR(376MHz,CDCl3)δ -116.64;ESIMS m/z 331([M+H]+)。
範例4,步驟2及3:製備(2R,3R,4S)-4-(苯甲氧基)-1-(4-氟苯基)戊烷-2,3-二醇:
於-15℃,對於DCM(94毫升)中之(3R,4R,5S)-5-(苯甲氧基)-3-(4-氟苯甲基)-4-羥基己-2-酮(3.12克,9.44毫莫耳)之溶液,添加過氧雙(三甲基矽烷)(4.00毫升,18.9毫莫耳)及三氟甲烷磺酸三甲基矽烷酯(TMSOTf;3.42毫升,18.9毫莫耳)。反應混合物於-10與-15℃之間攪拌50分鐘,以DCM稀釋,且以飽和含水NaHCO3及其後以飽和含水亞硫酸鈉(Na2SO3)抑制。反應混合物自冷浴移除,且相被分離。水相以DCM(2x)萃取,且混合之有機相依序以1N HCl及飽和含水NaHCO3清洗,於Na2SO4上乾燥,過
濾,及濃縮。形成之油藉由急速管柱層析術純化(SiO2,於己烷中1→50%丙酮)提供二乙酸酯位向異構物,個別係(2R,3S,4S)-4-(苯甲氧基)-1-(4-氟苯基)-3-羥基戊-2-基乙酸酯及(2R,3R,4S)-4-(苯甲氧基)-1-(4-氟苯基)-2-羥基戊-3-基乙酸酯之2:1混合物(3.01克,92%),呈蜂蜜色油。
對於MeOH(70毫升)及水(17毫升)中之乙酸酯位向異構物(3.01克,8.69毫莫耳)之溶液,添加碳酸鉀(K2CO3;6.00克,43.4毫莫耳),且混合物於室溫攪拌3小時,以DCM(100毫升)稀釋,並且倒至1N HCl(150毫升)內。相被分離,且水相以DCM(2x100毫升)萃取。混合之有機相通過一相分離器匣,且溶劑被蒸發。粗製之蠟質固體藉由急速管柱層析術純化(SiO2,於己烷中1→40%丙酮)提供標題化合物(1.60克,61%),呈白色固體:1H NMR(400MHz,CDCl3)δ 7.39-7.27(m,5H),7.18(dd,J=8.4,5.6Hz,2H),6.99(t,J=8.7Hz,2H),4.63(d,J=11.6Hz,1H),4.47(d,J=11.6Hz,1H),3.87-3.71(m,2H),3.66(dd,J=7.0,4.8Hz,1H),3.03(dd,J=13.9,2.9Hz,1H),2.66 dd,J=13.9,9.1Hz,1H),2.44(brs,1H),2.03(brs,1H),1.28(d,J=6.2Hz,3H);19F NMR(376MHz,CDCl3)δ -116.68;ESIMS m/z 305([M+H]+)。
範例5,步驟1:製備(2R,3S,4S)-2-(烯丙氧基)-4-(苯甲氧基)-1-(4-氟苯基)戊-3-醇:
對於CH3CN(60毫升)中之(2R,3R,4S)-4-(苯甲氧基)-1-(4-氟苯基)戊烷-2,3-二醇(1.81克,5.95毫莫耳)、2,2-二苯基-1,3,2-唑硼烷-3-鎓-2-鹽(0.134克,0.595毫莫耳)、碘化鉀(KI;0.987克,5.95毫莫耳),及K2CO3(0.986克,7.14毫莫耳)之溶液,添加烯丙基溴(0.772毫升,8.92毫莫耳),且反應混合物被加溫至60℃且於60℃攪拌隔夜。混合物經過塞里塑料過濾,並且濃縮。粗製油藉由急速管柱層析術純化(SiO2,於己烷中1→25% EtOAc)提供標題化合物(1.30克,64%),呈無色油:1H NMR(500MHz,CDCl3)δ 7.38-7.25(m,5H),7.19-7.11(m,2H),6.97-6.90(m,2H),5.69(ddt,J=16.4,10.8,5.6Hz,1H),5.11(d,J=17.2Hz,1H),5.07(d,J=10.3Hz,1H),4.60(d,J=11.6Hz,1H),4.40(d,J=11.5Hz,1H),3.84(ddd,J=12.8,5.7,1.6Hz,1H),3.79(ddd,J=12.6,5.7,1.6Hz,1H),3.71(dq,J=11.5,5.6Hz,2H),3.62(ddd,J=8.5,5.8,3.1Hz,1H),2.91(dd,J=14.2,3.2Hz,1H),2.76(dd,J=14.2,7.9Hz,1H),2.32(s,1H),1.29(d,J=5.9Hz,3H);13C NMR(126MHz,CDCl3)δ 161.49(d,J=243.7Hz),138.33,134.50,134.45(d,J=3.4Hz),131.14(d,J=7.7Hz),128.43,127.73,127.71,116.95,114.81(d,J=21.0Hz),79.95,75.07,73.41,71.06,70.57,34.85,14.74;
ESIMS m/z 345([M+H]+)。
範例5,步驟2A:製備(((2R,3S,4S)-2-(烯丙氧基)-4-(苯甲氧基)-1-(4-氟苯基)戊-3-基)氧)三異丙基矽烷:
於0℃,對於DCM(13毫升)中之(2R,3S,4S)-2-(烯丙氧基)-4-(苯甲氧基)-1-(4-氟苯基)戊-3-醇(1.3克,3.77毫莫耳)及2,6-二甲基吡啶(0.55毫升,4.72毫莫耳)之溶液,添加三氟甲烷磺酸三異丙基矽烷酯(1.27毫升,4.72毫莫耳)。於添加完全時,燒瓶自冷浴移除,且於室溫攪拌經過週末。反應以飽和含水NaHCO3抑制,且相被分離。水相以DCM(3x)萃取,且混合之有機相藉由通過一相分離器匣而乾燥。溶劑被分離,且粗製油藉由急速管柱層析術純化(SiO2,於己烷中0→10%丙酮)提供標題化合物(1.89克,100%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.34(d,J=4.4Hz,4H),7.31 7.27(m,1H),7.14-7.06(m,2H),6.96-6.85(m,2H),5.68-5.50(m,1H),5.04(dq,J=17.3,1.8Hz,1H),4.99(dq,J=10.4,1.4Hz,1H),4.61(d,J=11.7Hz,1H),4.45(d,J=11.7Hz,1H),3.96(dd,J=4.6,2.7Hz,1H),3.90(ddt,J=12.6,5.4,1.5Hz,1H),3.69-3.62(m,1H),3.62-3.56(m,2H),2.86(dd,J=14.0,3.6Hz,1H),2.76(dd,J=14.0,9.3Hz,1H),1.29(d,J=6.3Hz,3H),1.15-1.06(m,21H);19F NMR(376MHz,
CDCl3)δ -117.89;ESIMS m/z 523([M+Na]+)。
範例5,步驟2B:製備1-((2R,3S,4S)-2-(烯丙氧基)-4-(苯甲氧基)-3-(環丙基甲氧基)戊基)-4-甲氧基苯:
對於無水THF(10毫升)中之(2R,3S,4S)-2-(烯丙氧基)-4-(苯甲氧基)-1-(4-甲氧基苯基)戊-3-醇(340毫克,0.954毫莫耳)之溶液,添加第三丁氧化鉀(214毫克,1.908毫莫耳),且反應混合物於室溫攪拌15分鐘。形成之黃色溶液以(溴甲基)環丙烷(139μL,1.43毫莫耳)處理,且反應混合物於室溫攪拌20小時,以另外之第三丁氧化鉀(100毫克,1.36毫莫耳)及(溴甲基)環丙烷(70μL,0.72毫莫耳)處理,且加溫至40℃且於40℃攪拌4小時。反應被冷卻,以水(20毫升)稀釋,且以Et2O(3 x 20毫升)萃取。有機萃取液被混合,於MgSO4上乾燥,過濾,及濃縮提供一油,其藉由急速管柱層析術純化(SiO2)提供標題化合物與184毫克之回收起始材料。回收起始材料再次接受反應條件提供標題化合物(混合產量:285毫克,73%),呈無色油:1H NMR(500MHz,CDCl3)δ 7.37-7.26(m,5H),7.20-7.10(m,2H),6.85-6.76(m,2H),5.69(ddt,J=17.2,10.4,5.6Hz,1H),5.09(dq,J=17.2,1.7Hz,1H),5.06-5.01(m,1H),4.56(dd,J=11.8,2.6Hz,1H),4.42(d,J=11.8Hz,1H),3.83(ddt,J=12.6,5.6,1.4Hz,1H),
3.79(s,3H),3.73(ddt,J=12.6,5.6,1.4Hz,1H),3.69-3.61(m,2H),3.51(dd,J=6.9,2.1Hz,2H),3.42(t,J=5.1Hz,1H),2.92(dd,J=14.2,3.5Hz,1H),2.74(dd,J=14.2,8.4Hz,1H),1.28(d,J=6.2Hz,3H),1.16-1.04(m,1H),0.57-0.48(m,2H),0.26-0.20(m,2H);13C NMR(126MHz,CDCl3)δ 157.87,138.74,135.00,131.66,130.57,128.30,127.62,127.41,116.42,113.49,82.57,80.83,75.38,71.30,70.70,55.23,36.09,15.57,11.11,3.09,2.92;ESIMS m/z 411([M+H]+)。
範例6,步驟1及2:製備(Z)-4-((2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁氧基)-2-((第三丁氧基羰基)胺基)丁-2-烯酸甲酯:
對於DCM(20毫升)及MeOH(2毫升)中之1-((((2S,3R)-4-(烯丙氧基)-3-(苯甲氧基)丁-2-基)氧)甲基)-4-甲氧基苯(3.13克,8.78毫莫耳)之溶液,添加Sudan III指示劑(75μL之0.1% DCM溶液),且反應混合物於一乾冰/丙酮浴中冷卻至-78℃。燒瓶附接至一臭氧產生器,且O3起泡通過此溶液至溶液變無色為止(~30分鐘),然後,O2起泡通過此溶液持續5分鐘。仍於-78℃時,反應混合物以於DCM(5毫升)中之三苯基胺(PPh3;3.45克,13.2毫莫耳)之溶
液處理,且燒瓶自冷浴移除,裝設以N2之一氣球,且於室溫攪拌3小時。溶劑被蒸發提供中間物醛,2-((2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁氧基)乙醛,呈無色油。
對於DCM(30毫升)中之2-((2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁氧基)-乙醛及2-((第三丁氧基羰基)胺基)-2-(二甲氧基磷醯基)乙酸甲酯(2.66克,8.96毫莫耳)之溶液,於0℃添加2,3,4,6,7,8,9,10-八氫嘧啶并[1,2-a]吖呯(DBU;1.38毫升,9.22毫莫耳),且使反應混合物緩慢加溫至室溫,且攪拌18小時。溶劑被蒸發,且粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→40% EtOAc)提供標題化合物之一主要單一異構物(2.4克,46%),呈無色油:1H NMR(400MHz,CDCl3)主要異構物δ 7.39-7.29(m,4H),7.31-7.20(m,3H),6.90-6.81(m,2H),6.54-6.46(m,2H),4.76-4.60(m,2H),4.52(d,J=11.4Hz,1H),4.44(d,J=11.3Hz,1H),4.16(d,J=5.7Hz,2H),3.79(s,3H),3.79(s,3H),3.73-3.51(m,4H),1.45(s,9H),1.23(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)主要異構物δ 164.93,159.10,152.96,138.69,130.78,129.25,128.75,128.26,127.86,127.49,126.08,113.74,80.93,80.88,74.43,72.73,70.80,70.66,68.26,55.27,52.56,28.15,16.09;ESIMS m/z 531([M+H]+)。
範例6,步驟3:製備(S)-4-((2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁氧基)-2-((第三丁氧基羰基)
胺基)丁酸甲酯:
對於MeOH(23毫升)中之(Z)-4-((2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)氧)丁氧基)-2-((第三丁氧基羰基)胺基)丁-2-烯酸甲酯(2.4克,4.53毫莫耳)之溶液添加至一45毫升鋼質高壓反應器。溶液以N2噴射5分鐘,以(+)-三氟甲烷磺酸1,2-雙((2S,5S)-2,5-二乙基磷雜環戊烷基)苯(環辛二烯)銠(I)((S,S)-Et-DuPhos-Rh;0.033克,0.045毫莫耳)處理,且反應器被密封,以氫氣(H2)加壓至200磅/平方英射(psi),並且排氣。重複此方法3x後,反應器以H2加壓至200psi,且反應混合物於室溫劇烈攪拌15小時。溶劑被蒸發,且粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→50% EtOAc)提供標題化合物(2.04克,85%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.40-7.21(m,7H),6.91-6.82(m,2H),5.52(d,J=8.2Hz,1H),4.72(d,J=11.8Hz,1H),4.64(d,J=11.8Hz,1H),4.53(d,J=11.3Hz,1H),4.49-4.35(m,2H),3.80(s,3H),3.74-3.63(m,4H),3.60-3.47(m,5H),2.15-2.02(m,1H),2.06-1.94(m,1H),1.41(s,9H),1.23(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ 172.92,159.09,155.47,138.74,130.85,129.24,128.26,127.86,127.47,113.73,80.91,79.72,74.56,72.66,71.05,70.82,67.97,
55.28,52.21,51.96,31.84,28.32,16.05;ESIMS m/z 533([M+H]+)。
範例7,步驟1:製備(S)-4-(((2R,3S,4S)-4-(苯甲氧基)-1-(4-氟苯基)-3-((三異丙基矽烷基)氧)戊-2-基)氧)-2-((第三丁氧基羰基)胺基)丁酸:
對於THF(19毫升)及水(10毫升)中之(S)-4-(((2R,3S,4S)-4-(苯甲氧基)-1-(4-氟苯基)-3-((三異丙基矽烷基)氧)戊-2-基)氧)-2-((第三丁氧基羰基)胺基)丁酸甲酯(1.94克,2.87毫莫耳)之溶液,添加氫氧化鋰單水合物(LiOH.H2O;0.361克,8.61毫莫耳),且反應混合物於室溫攪拌3小時。混合物以EtOAc(50毫升)稀釋,且依序以0.2N HCl(50毫升)及鹽水清洗。有機相於Na2SO4上乾燥,過濾,及濃縮提供標題化合物(1.9克,100%),呈白色發泡劑:1H NMR(400MHz,CDCl3)δ 7.36-7.32(m,4H),7.32-7.27(m,1H),7.12-7.04(m,2H),6.97-6.85(m,2H),5.34(d,J=7.1Hz,1H),4.63(d,J=11.6Hz,1H),4.46(d,J=11.6Hz,1H),4.07(q,J=7.1,5.6Hz,1H),3.94(dd,J=4.9,2.1Hz,1H),3.71-3.58(m,3H),3.25(s,1H),2.89(dd,J=14.3,3.8Hz,1H),2.77(dd,J=14.3,9.5Hz,1H),1.96(ddt,J=14.7,9.8,4.9Hz,1H),1.90-1.81(m,1H),1.45(s,9H),1.30(d,J=6.2Hz,3H),
1.09(q,J=2.7,2.1Hz,21H);19F NMR(376MHz,CDCl3)δ -116.99;ESIMS m/z 684([M+Na]+)。
範例7,步驟2:製備(S)-2-((第三丁氧基羰基)胺基)-4-(((2R,3S,4S)-1-(4-氟苯基)-4-羥基-3-((三異丙基矽烷基)氧)戊-2-基)氧)丁酸:
對於EtOAc(9.6毫升)中之(S)-4-(((2R,3S,4S)-4-(苯甲氧基)-1-(4-氟苯基)-3-((三異丙基-矽烷基)氧)戊-2-基)氧)-2-((第三丁氧基羰基)胺基)丁酸(635毫克,0.959毫莫耳)之溶液,添加10%之於碳上的鈀(Pd/C;51.0毫克,0.048毫莫耳)。混合物置於約1大氣壓(氣球)之H2下,且燒瓶於真空下抽空(重複2x)。反應混合物再次置於H2氛圍下,且於室溫攪拌隔夜。混合物經過一塞里塑料墊材過濾,並且濃縮提供標題化合物(540毫克,98%),呈白色發泡體:1H NMR(400MHz,CDCl3)δ 7.19(dd,J=8.5,5.5Hz,2H),6.97(t,J=8.7Hz,2H),5.38-5.24(m,1H),4.19(q,J=5.8Hz,1H),3.99(dt,J=11.2,6.2Hz,1H),3.82(dd,J=5.0,2.0Hz,1H),3.68-3.52(m,2H),3.32-3.15(m,1H),2.97(dd,J=14.2,4.3Hz,1H),2.85(dd,J=14.2,9.3Hz,1H),2.05-1.93(m,1H),1.93-1.81(m,1H),1.45(s,9H),1.29(d,J=6.4Hz,3H),1.08(s,21H);19F NMR(376MHz,CDCl3)δ
-116.94;ESIMS m/z 594([M+Na]+)。
範例8,步驟1:製備(S)-4-((2R,3S)-2-(苯甲氧基)-3-羥基丁氧基)-2-((第三丁氧基羰基)胺基)丁酸甲酯:
對於DCM(14毫升)及H2O(1.4毫升)中之(S)-4-((2R,3S)-2-(苯甲氧基)-3-((4-甲氧基苯甲基)-氧)丁氧基)-2-((第三丁氧基羰基)胺基)丁酸甲酯(2.04克,3.84毫莫耳)之溶液,於0℃添加4,5-二氯-3,6-二氧代環己-1,4-二烯-1,2-二甲腈(DDQ;0.915克,4.03毫莫耳),且混合物於此溫度劇烈攪拌1小時。反應混合物於1N氫氧化鈉(NaOH;4.03毫升,4.03毫莫耳)、H2O(20毫升),及DCM(20毫升)間分配,且相被分離。水相以DCM(3x25毫升)萃取,且混合之有機相以鹽水(10毫升)清洗,藉由通過一相分離器匣乾燥,及蒸發。粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中0→80% EtOAc)提供標題化合物(1.22克,77%),呈無色油:1H NMR(400MHz,CDCl3)δ 7.40-7.25(m,5H),5.41(d,J=8.6Hz,1H),4.71(d,J=11.8Hz,1H),4.62-4.46(m,2H),4.04(q,J=6.1Hz,1H),3.73(s,3H),3.64-3.52(m,3H),3.45-3.28(m,2H),3.17(d,J=5.1Hz,1H),2.25-2.11(m,1H),1.88-1.73(m,1H),1.43(s,9H),1.24(d,J=6.4Hz,3H);13C NMR(126MHz,CDCl3)δ 173.21,155.53,138.34,128.37,
127.93,127.71,82.08,80.09,72.31,69.68,67.34,66.83,52.35,51.16,32.66,28.32,19.22;ESIMS m/z 413([M+H]+)。
範例8,步驟2:製備(S)-4-((2R,3S)-2-(苯甲氧基)-3-羥基丁氧基)-2-((第三丁氧基羰基)胺基)丁酸:
對於THF(7.8毫升)及H2O(3.9毫升)中之(S)-4-((2R,3S)-2-(苯甲氧基)-3-羥基丁氧基)-2-((第三丁氧基羰基)胺基)丁酸甲酯(1.21克,2.94毫莫耳)之溶液,添加LiOH.H2O(0.370克,8.82毫莫耳),且反應混合物於室溫攪拌4小時。混合物以Et2O(30毫升)稀釋,且以1N HCl(11.8毫升,11.8毫莫耳)抑制。相被分離,且水相以Et2O(2x30毫升)萃取。混合之有機相以鹽水(15毫升)清洗,於Na2SO4上乾燥,及過濾。然後,溶劑被蒸發提供標題化合物(1.17克,100%),呈黏稠油:1H NMR(500MHz,CDCl3)δ 7.38-7.25(m,5H),5.56(d,J=7.7Hz,1H),4.69(d,J=11.8Hz,1H),4.58(d,J=11.8Hz,1H),4.46(d,J=6.1Hz,1H),4.02(q,J=6.4Hz,1H),3.67-3.56(m,3H),3.49(dt,J=9.9,5.0Hz,1H),3.39-3.33(m,1H),2.18(d,J=3.9Hz,1H),1.97(s,1H),1.43(s,9H),1.23(d,J=6.4Hz,3H);13C NMR(126MHz,CDCl3)δ 175.20,155.81,138.12,128.41,127.97,127.80,81.61,
80.32,72.30,69.69,67.68,67.21,51.40,32.12,28.31,19.06;ESIMS m/z 399([M+H]+)。
範例9:製備((3R,4S,7S)-3-(苯甲氧基)-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(化合物23):
對於DCM(294毫升)中之2-甲基-6-硝基苯甲酸酐(MNBA;2.03克,5.88毫莫耳)及N,N-二甲基吡啶-4-胺(DMAP;2.16克,17.7毫莫耳)之攪拌溶液,於室溫,於5小時期間使用一注射幫浦添加於DCM(147毫升,0.02M)中之(S)-4-((2R,3S)-2-(苯甲氧基)-3-羥基丁氧基)-2-((第三丁氧基羰基)胺基)-丁酸(1.17克,2.94毫莫耳)之溶液。於添加完全時,反應混合物於室溫攪拌隔夜,然後,溶劑被蒸發。殘餘物以DCM(50毫升)及塞里塑料處理,且溶劑被蒸發。吸附之材料使用急速管柱層析術純化(SiO2,於己烷中0→60% EtOAc)提供標題化合物(900毫克,81%),呈黏性油:1H NMR(400MHz,CDCl3)δ 7.37-7.28(m,5H),5.32(d,J=7.3Hz,1H),5.23(p,J=6.6Hz,1H),4.65-4.51(m,2H),4.28(q,J=7.2Hz,1H),3.86-3.78(m,1H),3.73(dd,J=11.8,5.6Hz,1H),3.58(dd,J=11.8,3.6Hz,1H),3.52-3.38(m,2H),2.40-2.24(m,1H),1.78-1.68(m,1H),1.44(s,9H),1.35(d,J=6.7Hz,3H);13C NMR(101MHz,CDCl3)δ 172.89,155.04,
137.75,128.45,127.89,127.85,79.82,78.38,73.48,72.22,68.57,66.20,51.31,33.15,28.33,18.92;ESIMS m/z 381([M+H]+)。
範例10:製備((2R,3S,4S,7S)-2-(4-氟苯甲基)-3-羥基-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(化合物4):
對於THF(20毫升)中之((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-((三異丙基矽烷基)氧)-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(1.11克,2.00毫莫耳)之溶液,於0℃,以滴液方式添加四丁基氟化銨(TBAF;2.4毫升,2.40毫莫耳,於THF中,1M),且反應混合物於0℃攪拌30分鐘。混合物以EtOAc稀釋,以飽和含水NaHCO3抑制,且相被分離。水相以EtOAc(3x)萃取,且混合之有機相以鹽水清洗,於Na2SO4上乾燥,過濾,及濃縮。粗製淡黃色油藉由急速管柱層析術純化(SiO2,於己烷中1→35%丙酮)提供標題化合物(535毫克,67%),呈白色固體:1H NMR(400MHz,CDCl3)δ 7.20(dd,J=8.5,5.5Hz,2H),6.96(t,J=8.7Hz,2H),5.17(d,J=8.2Hz,1H),5.04(dq,J=13.0,6.7Hz,1H),4.22(q,J=8.3Hz,1H),3.75(ddd,J=10.5,9.1,3.0Hz,1H),3.59(td,J=9.2,6.8Hz,1H),3.51(t,J=9.8Hz,1H),3.47-3.42(m,1H),
3.14(dd,J=15.2,2.9Hz,1H),2.84(dd,J=15.2,10.6Hz,1H),2.53(d,J=6.9Hz,1H),2.25-2.10(m,1H),1.51(dtd,J=14.4,10.2,2.4Hz,1H),1.42(d,J=6.6Hz,3H),1.42(s,9H);19F NMR(376MHz,CDCl3)δ -116.91;ESIMS m/z 420([M+Na]+)。
範例11:製備((3R,4S,7S)-3-羥基-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(化合物24):
於THF(9毫升)中之((3R,4S,7S)-3-(苯甲氧基)-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(715毫克,1.88毫莫耳)之溶液以10% Pd/C(60.2毫克,0.057毫莫耳)處理。反應混合物被置於約1大氣壓(氣球)之H2下,且燒瓶於真空下抽空(重複2x)。反應混合物再次置於H2氛圍下,且非均質混合物於室溫攪拌5小時。混合物通過一塞里塑料墊材過濾,並且濃縮提供標題化合物(518毫克,95%),呈白色固體:1H NMR(400MHz,CDCl3)δ 5.39-5.29(m,1H),5.25(d,J=7.7Hz,1H),4.35-4.24(m,1H),4.07(ddd,J=10.9,5.9,2.8Hz,1H),3.95(ddd,J=11.2,4.3,1.1Hz,1H),3.50-3.39(m,3H),3.12(d,J=11.1Hz,1H),2.33-2.21(m,1H),1.80-1.66(m,1H),1.44(s,9H),1.32(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ 174.77,155.08,80.00,76.97,73.57,70.29,68.57,51.42,33.55,28.30,18.47;ESIMS m/z 312([M+Na]+)。
範例12A:製備(2R,3S,4S,7S)-7-((第三丁氧基羰基)胺基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-3-基異丁酸酯(化合物8):
對於DCM(3.8毫升)中之((2R,3S,4S,7S)-2-(4-氟苯甲基)-3-羥基-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(150毫克,0.377毫莫耳)及DMAP(9.22毫克,0.075毫莫耳)之溶液,於0℃添加三乙胺(NEt3;210μL,1.51毫莫耳)及異丁醯氯(59.3μL,0.566毫莫耳),且反應緩慢加溫至室溫,並且攪拌隔夜。另外之異丁醯氯(40μL,0.38毫莫耳)及NEt3(105μL,0.76毫莫耳)於室溫添加,且反應攪拌隔夜。反應以DCM稀釋,且以飽和含水NH4Cl抑制。相被分離,且水相以DCM(3x)萃取。混合之有機相藉由通過一相分離器匣乾燥,然後,溶劑被蒸發。粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中1→25%丙酮)提供標題化合物(159.9毫克,91%),呈白色發泡體:1H NMR(400MHz,CDCl3)δ 7.15(dd,J=8.6,5.4Hz,2H),6.97(t,J=8.7Hz,2H),5.27-5.17(m,1H),5.14(t,J=9.4Hz,1H),5.08(d,J=8.2Hz,1H),4.27(q,J=8.4Hz,1H),3.95(ddd,J=10.6,9.3,3.3Hz,1H),3.62(t,J=10.1Hz,1H),3.50-3.42(m,1H),2.87(dd,J=15.4,10.7Hz,1H),2.60(dd,J=15.2,3.1Hz,
1H),2.50(hept,J=7.0Hz,1H),2.22(dt,J=14.9,7.0Hz,1H),1.591.47(m,1H),1.43(s,9H),1.27(d,J=6.3Hz,3H),1.18(d,J=7.0Hz,3H),1.17(d,J=7.0Hz,3H);19F NMR(376MHz,CDCl3)δ -116.62;ESIMS m/z 490([M+Na]+)。
範例12B:製備((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-苯氧基-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(化合物5):
對於甲苯(2.5毫升)中之((2R,3S,4S,7S)-2-(4-氟苯甲基)-3-羥基-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(150毫克,0.377毫莫耳)之溶液,添加二乙醯氧銅(6.86毫克,0.038毫莫耳)、Bi(OAc)2Ph3(316毫克,0.566毫莫耳),及N,N-二環己基甲胺(96μL,0.453毫莫耳)。反應容器於真空下抽空,且以N2回填(重複4x),密封,且反應混合物於40℃攪拌經過週末。混合物經過塞里塑料過濾(以EtOAc沖洗),並且濃縮,且形成之油藉由急速管柱層析術純化(SiO2,於己烷中1→25%丙酮)提供標題化合物(83.9毫克,47%),呈白色固體:1H NMR(400MHz,CDCl3)δ 7.33-7.27(m,2H),7.15(dd,J=8.5,5.5Hz,2H),7.02-6.90(m,5H),5.33-5.19(m,1H),5.17(d,J=8.1Hz,1H),4.44(t,J=9.2Hz,1H),4.29(q,J=8.1Hz,1H),4.01(td,J=10.3,9.1,
2.8Hz,1H),3.58(t,J=9.8Hz,1H),3.50-3.38(m,1H),2.96-2.87(m,1H),2.78(dd,J=15.1,11.1Hz,1H),2.25-2.18(m,1H),1.86-1.71(m,1H),1.43(s,9H),1.36(d,J=6.5Hz,3H);;19F NMR(376MHz,CDCl3)δ -116.86;ESIMS m/z 496([M+Na]+)。
範例12C,步驟1:製備((2R,3S,4S,7S)-3-(烯丙氧基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(化合物9):
於THF(7.5毫升)中之((2R,3S,4S,7S)-2-(4-氟苯甲基)-3-羥基-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(300毫克,0.755毫莫耳)、Pd2(dba)3(34.6毫克,0.038毫莫耳),及dppf(41.8毫克,0.075毫莫耳)之磁性攪拌混合物加熱至60℃,且於9分鐘期間,以於THF(1毫升)中之碳酸烯丙基第三丁酯(239μL,1.51毫莫耳)之溶液以滴液方式處理。反應混合物於60℃攪拌另外20分鐘,冷卻至室溫,且經過以EtOAc沖洗之塞里塑料過濾。濾液被濃縮,且藉由急速管柱層析術純化(SiO2,於己烷中1→20%丙酮)提供標題化合物(223.5毫克,68%),呈白色發泡體:1H NMR(400MHz,CDCl3)δ 7.20(dd,J=8.6,5.5Hz,2H),6.97(t,J=8.7Hz,2H),5.89(ddt,J=17.2,10.4,5.6Hz,1H),5.30(dq,J=17.2,
1.6Hz,1H),5.21(dq,J=10.3,1.3Hz,1H),5.10(d,J=8.2Hz,1H),5.07-5.01(m,1H),4.28-4.18(m,2H),4.08(ddt,J=12.2,5.7,1.4Hz,1H),3.85-3.74(m,1H),3.48(t,J=9.8Hz,1H),3.36(q,J=9.2,8.6Hz,2H),3.05(d,J=14.8Hz,1H),2.79(dd,J=14.9,11.2Hz,1H),2.21-2.10(m,1H),1.57-1.48(m,1H),1.47(d,J=6.7Hz,3H),1.42(s,9H);19F NMR(376MHz,CDCl3)δ -117.01;ESIMS m/z 460([M+Na]+)。
範例12C,步驟2:製備((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(化合物10):
對於EtOAc(2.5毫升)中之((2R,3S,4S,7S)-3-(烯丙氧基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(110毫克,0.251毫莫耳)之溶液,添加10%Pd/C(13.4毫克,0.013毫莫耳)。混合物置於約1大氣壓(氣球)之H2下,且燒瓶於真空下抽空(重複2x)。反應混合物再次置於H2氛圍下,並且於室溫攪拌隔夜。混合物經過一塞里塑料墊材過濾,並且濃縮提供標題化合物(110毫克,100%),呈白色發泡體:1H NMR(400MHz,CDCl3)δ 7.20(dd,J=8.5,5.5Hz,2H),6.97(t,J=8.7Hz,2H),5.13(d,J=8.2Hz,1H),5.07-4.97(m,1H),4.22(q,J=8.3Hz,1H),3.76(ddd,J=11.6,
9.2,2.6Hz,1H),3.66(dt,J=8.6,6.6Hz,1H),3.57-3.44(m,2H),3.43-3.34(m,1H),3.26(t,J=9.2Hz,1H),3.02(dd,J=14.9,2.5Hz,1H),2.80(dd,J=14.9,11.2Hz,1H),2.23-2.09(m,1H),1.66-1.52(m,2H),1.54-1.47(m,1H),1.46(d,J=7.1Hz,3H),1.42(s,9H),0.94(t,J=7.4Hz,3H);19F NMR(376MHz,CDCl3)δ -117.06;ESIMS m/z 440([M+H]+)。
範例13A,步驟1及2:製備N-((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)-3-羥基-4-甲氧基吡啶醯胺(化合物36及56):
對於DCM(1.7毫升)中之((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(111毫克,0.253毫莫耳)之溶液,添加於二
烷中之HCL的4N溶液(1.26毫升,5.05毫莫耳)。於室溫2.5小時後,溶劑於N2流下蒸發提供中間物胺氫氯酸鹽,(2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-氯化銨,呈淡黃色固體:ESIMS m/z 340([M+H]+)。
對於DCM(1.7毫升)中之(2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-氯化銨及3-羥基-4-甲氧基吡啶甲酸(47.0毫克,0.278毫莫耳)之溶液,添加N-乙基-N-異丙基丙-2-胺(145μL,0.833毫莫耳)及苯并三唑-1-基氧)三吡咯啶基鏻六氟磷酸鹽(PyBOP;145毫克,0.278毫莫耳),且反應混合物於N2下於室溫攪拌4小時。溶劑被蒸發,且粗製油藉由急速管柱層析術純化(SiO2,於己烷中1→50%丙酮)提供標題化合物(117毫克,94%),呈白色固體:1H NMR(400MHz,CDCl3)δ 12.06(s,1H),8.53(d,J=8.0Hz,1H),7.97(d,J=5.2Hz,1H),7.22(dd,J=8.5,5.5Hz,2H),6.98(t,J=8.7Hz,2H),6.85(d,J=5.2Hz,1H),5.12-4.99(m,1H),4.62(td,J=8.5,7.1Hz,1H),3.93(s,3H),3.81(ddd,J=11.5,9.2,2.6Hz,1H),3.67(dt,J=8.6,6.6Hz,1H),3.60-3.48(m,2H),3.48-3.37(m,1H),3.31(t,J=9.2Hz,1H),3.11-3.00(m,1H),2.82(dd,J=14.9,11.2Hz,1H),2.35-2.24(m,1H),1.76-1.62(m,1H),1.60(h,J=7.1Hz,2H),1.50(d,J=6.5Hz,3H),0.95(t,J=7.4Hz,3H);19F NMR(376MHz,CDCl3)δ -117.01;HRMS-ESI(m/z)[M+H]+對於
C25H32FN2O7計算,491.2188;發現,491.2183。
範例13B,步驟1及2:製備N-((2R,3S,4S,7S)-3-(烯丙氧基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-7-基)-3-羥基-4-甲氧基吡啶醯胺(化合物35及55):
對於DCM(2.5毫升)中之((2R,3S,4S,7S)-3-(烯丙氧基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-7-基)氨基甲酸第三丁酯(111毫克,0.254毫莫耳)之溶液,於室溫以滴液方式添加2,6-二甲基吡啶(89μL,0.76毫莫耳),其後添加三氟甲烷磺酸三甲基矽烷酯(92μL,0.51毫莫耳),且反應混合物於N2下於室溫攪拌1.5小時。反應混合物以MeOH(0.9毫升)處理,且攪拌隔夜。溶劑被蒸發提供中間物三氟甲烷磺酸銨,(2R,3S,4S,7S)-3-(烯丙氧基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-7-三氟甲烷磺酸銨:ESIMS m/z 338([M+H]+)。
對於DCM(2.5毫升)中之(2R,3S,4S,7S)-3-(烯丙氧基)-2-(4-氟苯甲基)-4-甲基-6-氧代-1,5-二氧環戊-7-三氟甲烷磺酸銨及3-羥基-4-甲氧基吡啶甲酸(47.2毫克,0.279毫莫耳)之溶液,添加N-乙基-N-異丙基丙-2-胺(146μL,0.837毫莫耳)及PyBOP(145毫克,0.279毫莫耳),且反應混合物於N2下於室溫攪拌隔夜。溶劑被蒸發,且形成之油藉由急速管柱層析術純化(SiO2,於己烷中1→40%丙酮)提供標題化合物(107毫克,86%),呈白色發泡體:1H NMR(400MHz,CDCl3)δ 12.06(s,1H),8.52(d,J=7.9Hz,1H),7.96(d,J=5.2Hz,1H),7.22(dd,J=8.5,5.5Hz,2H),6.97(t,J=8.7Hz,2H),6.85(d,J=5.3Hz,1H),5.90(ddt,J=17.2,10.4,5.6Hz,1H),5.31(dq,J=17.2,1.6Hz,1H),5.21(dq,J=10.4,1.3Hz,1H),5.14-5.01(m,1H),4.62(td,J=8.5,7.0Hz,1H),4.24(ddt,J=12.2,5.5,1.4Hz,1H),4.10(ddt,J=12.2,5.7,1.4Hz,1H),3.92(s,3H),3.84(ddd,J=11.6,9.2,2.6Hz,1H),3.55(t,J=9.6Hz,1H),3.49-3.41(m,1H),3.40(t,J=9.6Hz,1H),3.08(dt,J=14.7,2.0Hz,1H),2.88-2.79(m,1H),2.38-2.22(m,1H),1.79-1.62(m,1H),1.51(d,J=6.6Hz,3H);19F NMR(376MHz,CDCl3)δ -116.94;HRMS-ESI(m/z)[M+H]+對於C25H30FN2O7計算,489.2032;發現,489.2032。
範例14:製備2-(((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)氨基甲醯基)-4-甲氧基吡啶-3-基乙酸酯(化合物81):
對於DCM(0.8毫升)中之N-((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)-3-羥基-4-甲氧基吡啶醯胺(38毫克,0.077毫莫耳)、NEt3(21.5μL,0.155毫莫耳),及DMAP(1.9毫克,0.015毫莫耳)之溶液,添加氯化乙醯(8.3μL,0.116毫莫耳),且反應混合物於室溫攪拌3小時。混合物以DCM稀釋,倒至飽和含水NH4Cl內,且相被分離。水相以DCM(3x)萃取,且混合之有機相藉由通過一相分離器匣乾燥,並且濃縮。形成之粗製油藉由急速管柱層析術純化(SiO2,於己烷中1→50%丙酮)提供標題化合物(40.9毫克,100%),呈白色發泡體:1H NMR(400MHz,CDCl3)δ 8.57(d,J=8.1Hz,1H),8.31(d,J=5.4Hz,1H),7.21(dd,J=8.6,5.5Hz,2H),7.03-6.90(m,3H),5.19-4.95(m,1H),4.62(td,J=8.7,7.1Hz,1H),3.89(s,3H),3.79(ddd,J=11.5,9.2,2.6Hz,1H),3.66(dt,J=8.6,6.6Hz,1H),3.56-3.47(m,2H),3.46-3.39(m,1H),3.29(t,J=9.2Hz,1H),3.09-3.00(m,1H),2.81(dd,J=14.9,11.2Hz,1H),
2.38(s,3H),2.34-2.22(m,1H),1.71-1.52(m,3H),1.47(d,J=6.5Hz,3H),0.94(t,J=7.4Hz,3H);19F NMR(376MHz,CDCl3)δ -117.10;HRMS-ESI(m/z)[M+H]+對於C27H34FN2O8計算,533.2294;發現,533.2295。
範例15:製備((2-(((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)氨基甲醯基)-4-甲氧基吡啶-3-基)氧)甲基乙酸酯(化合物79):
對於丙酮(1.2毫升)中之N-((2R,3S,4S,7S)-2-(4-氟苯甲基)-4-甲基-6-氧代-3-丙氧基-1,5-二氧環戊-7-基)-3-羥基-4-甲氧基吡啶醯胺(60毫克,0.122毫莫耳)及碳酸鉀(K2CO3;33.8毫克,0.245毫莫耳)之溶液,以滴液方式添加乙酸溴甲酯(16.8μL,0.171毫莫耳)。反應容器被密封,且混合物加溫至55℃且於55℃攪拌3小時。混合物經過以己烷及丙酮之3:1混合物沖洗之一燒結過濾器過濾。溶劑被蒸發,且粗製殘餘物藉由急速管柱層析術純化(SiO2,於己烷中1→50%丙酮)提供標題化合物(47.7毫克,69%),呈白色發
泡體:1H NMR(400MHz,CDCl3)δ 8.36(d,J=7.9Hz,1H),8.26(d,J=5.3Hz,1H),7.22(dd,J=8.5,5.5Hz,2H),6.97(t,J=8.7Hz,2H),6.94(d,J=5.5Hz,1H),5.72(s,2H),5.13-4.95(m,1H),4.71-4.56(m,1H),3.90(s,3H),3.80(ddd,J=11.5,9.2,2.6Hz,1H),3.67(dt,J=8.6,6.5Hz,1H),3.60-3.47(m,2H),3.47-3.40(m,1H),3.30(t,J=9.2Hz,1H),3.05(dt,J=14.8,2.0Hz,1H),2.83(dd,J=15.0,11.2Hz,1H),2.38-2.24(m,1H),2.05(s,3H),1.70-1.63(m,1H),1.60(h,J=7.1Hz,2H),1.48(d,J=6.5Hz,3H),0.95(t,J=7.4Hz,3H);19F NMR(376MHz,CDCl3)δ -117.11;HRMS-ESI(m/z)[M+H]+對於C28H36FN2O9計算,563.2399;發現,563.2404。
範例A:評估殺真菌活性:小麥葉斑病(禾生球腔菌(Mycosphaerella graminicola);無性態:枯葉病菌(Zymoseptoria tritici);拜耳(Bayer)編碼SEPTTR):工業級材料溶於丙酮,然後,與9份體積之含有110ppm之Triton X-100的水混合。殺真菌劑溶液係使用自動化棚噴灑器流出施用於小麥苗上。所有經噴灑之植物於進一步處理前係以空氣乾燥。除非其它陳述,所有殺真菌劑係使用前述方法評估其等對於所有目標疾病之活性。小麥葉斑病及葉銹病之活性亦使用軌道噴灑施用評估,於此情況,殺真菌劑係調配成EC調配物,其於噴灑溶液中含有0.1% Trycol 5941。
小麥植物(Yuma變種)係於溫室中,於50%礦物土/50%無土Metro混合物中自種籽生長至初生葉完全完全顯
見為止,每一盆具有7-10個苗。於殺真菌劑處理之前或之後,此等植物係以枯葉病菌(Zymoseptoria tritici)之含水孢子懸浮液接種。接種後,植物保持於100%相對濕度(於20℃,於一暗露水室內一天,其後,於亮露水室中二至三天)使孢子發芽及使葉子感染。然後,植物移至設定為20℃之溫室以供疾病發展。當疾病症狀於未經處理之植物之第一葉子上完全表現出時,感染程度以0至100%疾病嚴重度之等級評估。疾病控制百分率係使用經處理之植物相對於未經處理之植物的疾病嚴重比率計算。
範例B:評估殺真菌活性:小麥葉銹病(小麥葉锈菌(Puccinia triticina);同義字:小麥葉锈病菌(Puccinia recondita f.sp.tritici);拜耳編碼PUCCRT):小麥植物(Yuma變種)係於溫室中,於50%礦物土/50%無土Metro混合物中自種籽生長至初生葉完全完全顯見為止,每一盆具有7-10個苗。於殺真菌劑處理之前或之後,此等植物係以小麥葉锈菌之含水抱子懸浮液接種。接種後,植物保持於22℃及100%相對濕度,於一暗露水室內隔夜,使孢子發芽及使葉子感染。然後,植物移至設定為24℃之溫室以供疾病發展。殺生真菌劑之調配及施用與疾病評估係依循範例A中所述之程序。
範例C:評估殺真菌活性:小麥穎枯病(穎枯殼小球腔菌(Leptosphaeria nodorum);拜耳編碼LEPTNO):小麥植物(Yuma變種)係於溫室中,於50%礦物土/50%無土Metro混合物中自種籽生長至初生葉完全完全顯
見為止,每一盆具有7-10個苗。於殺真菌劑處理24小時後,此等植物係以穎枯殼小球腔菌之含水孢子懸浮液接種。接種後,植物保持於100%相對濕度(於20℃,於一暗露水室內一天,其後,於亮露水室中兩天)使孢子發芽及使葉子感染。然後,植物移至設定為20℃之溫室以供疾病發展。殺生真菌劑之調配及施用與疾病評估係依循範例A中所述之程序。
範例D:評估殺真菌活性:蘋果黑星病(蘋果黑星菌(Venturia inaequalis);拜耳編碼VENTIN):蘋果苗(McIntosh變種)於無土Metro混合物中生長,且每一盆一棵植物。於頂部具有二展開中嫩葉之苗(植物底部之較老葉子被修剪)被用於此測試。於殺真菌劑處理24小時後,植物係以蘋果黑星菌之孢子懸浮液接種,且於具100%相對濕度之22℃的暗露水室內保持48小時,然後,移至設定為20℃之溫室以供疾病發展。殺生真菌劑之調配及施用與於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例E:評估殺真菌活性:葡萄白粉病(葡萄鉤絲霉菌(Uncinula necator);拜耳編碼UNCINE):葡萄苗(Carignane變種)於無土Metro混合物中生長,且每一盆一棵植物,且於約1個月大時用於測試。於殺真菌劑處理24小時後,植物係藉由使孢子自受感染的葉子搖至測試植物上而接種,植物被維持於設定為20℃之溫室至疾病發展為止。殺生真菌劑之調配、施用及於經噴灑之
葉子上的疾病評估係依循範例A中所述之程序。
範例F:評估殺真菌活性:小黃瓜白粉病(二孢白粉菌(Erysiphe cichoracearum);拜耳編碼ERYSCI):小黃瓜苗(Bush Pickle變種)於無土Metro混合物中生長,且每一盆一棵植物,且於12至14天大時用於測試。於殺真菌劑處理24小時後,植物以一孢子懸浮液接種。接種後,植物被維持於設定為20℃之溫室至疾病完全表現為止。殺生真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例G:評估殺真菌活性:甜菜葉斑病(甜菜生尾孢菌(Cercospora beticola);拜耳編碼CERCBE):甜菜植物(HH88變種)於無土Metro混合物中生長,且於測試前規律修剪以維持一均勻尺寸。於殺真菌劑處理24小時後,植物以一孢子懸浮液接種。經接種之植物於22℃之露水室中維持48小時,然後,於設定為24℃之溫室中於具有底部通風之一透明塑膠殼下培養至完全表現為止。殺生真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例H:評估殺真菌活性:亞洲大豆銹病(豆薯層銹菌(Phakopsora pachyrhizi);拜耳編碼PHAKPA):工業級材料溶於丙酮,然後,與9份體積之含有0.011%之Tween 20的水混合。殺真菌劑溶液係使用自動化棚噴灑器流出施用於大豆苗上。所有經噴灑之植物於進一步處理前係以空氣乾燥。
大豆植物(Williams 82變種)於無土Metro混合物中生長,且每一盆具有1棵植物。二週大的苗被用於測試。植物於殺真菌劑處理前3天或處理後1天接種。植物於22℃及100%相對濕度之一暗露水室內培養24小時,然後,移至23℃之一生長室以供疾病發展。疾疾嚴重性係於經噴灑之葉子上評估。
範例I:評估殺真菌活性:小麥白粉病(小麥白粉菌(Blumeria graminis f.sp.tritici);同義字:小麥白粉病菌(Erysiphe graminis f.sp.tritici);拜耳編碼ERYSGT):小麥植物(Yuma變種)於一溫室於50%礦物土/50%無土Metro混合物中自種籽生長至初生葉完全完全顯見為止,每一盆具有7-10個苗。於殺真菌劑處理後24小時,此等植物係藉由以受感染之母株撒粉而接種。接種後,植物維持於設定為20℃之一溫室中以供疾病發展。殺真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例J:評估殺真菌活性:大麥白粉病(大麥白粉菌(Blumeria graminis f.sp.hordei);同義字:大麥白粉病菌(Erysiphe graminis f.sp.hordei);拜耳編碼ERYSGH):大麥苗(Harrington變種)於無水Metro混合物中增殖,且每一盆具有8至12棵植物,且於初生葉完全完全顯見時用於測試。於殺真菌劑處理後24小時,測試植物藉由以受感染之母株撒粉而接種。接種後,植物維持於設定為20℃之一溫室中以供疾病發展。殺真菌劑之調配、施用及於經
噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例K:評估殺真菌活性:大麥雲紋病(大麥雲紋病菌(Rhyncosporium secalis);拜耳編碼RHYNSE):大麥苗(Harrington變種)於無土Metro混合物中增殖,且每一盆具有8至12棵植物,且於初生葉完全完全顯見時用於測試。於殺真菌劑處理後24小時,測試植物以大麥雲紋病菌之含水孢子懸浮液接種。接種後,植物於20℃及100%相對濕度之一露水室中保持48小時。然後,植物移至設定於20℃之一溫室以供疾病發展。殺真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例L:評估殺真菌活性:稻瘟病(稻瘟菌(Magnaporthe grisea);同義字:稻瘟病菌(Pyricularia oryzae);拜耳編碼PYRIOR):稻苗(Japonica變種)於無土Metro混合物中增殖,且每一盆具有8至14棵植物,且於12至14天大時用於測試。於殺真菌劑處理後24小時,測試植物以稻溫菌之含水孢子懸浮液接種。接種後,植物於22℃及100%相對濕度之一露水室中保持48小時以使孢子發芽及使葉子感染。然後,植物移至設定於24℃之一溫室以供疾病發展。殺真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例M:評估殺真菌活性:蕃茄早疫病(茄鏈隔孢菌(Alternaria solani);拜耳編碼ALTESO):
蕃茄植物(Outdoor Girl變種)於無土Metro混合物中增殖,且每一盆具有一棵植物,且於12至14天大時使用。於殺真菌劑處理24小時後,測試植物以茄鏈隔孢菌之含水孢子懸浮液接種。接種後,植物保持於100%相對濕度(於一暗露水室內一天,然後,於20℃之一亮露水室中二至三天)以使抱子發芽及使葉子感染。然後,植物移至設定於22℃之一生長室以供疾病發展。殺真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
範例N:評估殺真菌活性:小黃瓜炭疽病(瓜類小蟲殼(Glomerella lagenarium);無性型:瓜類炭疽菌(Colletotrichum lagenarium);拜耳編碼COLLLA):小黃瓜苗(Bush Pickle變種)於無水Metro混合物中增殖,且每一盆具有一棵植物,且於12至14天小用於測試。於殺真菌劑處理24小時後,測試植物以瓜類炭疽菌之含水孢子懸浮液接種。接種後,植物於22℃及100%相對濕度之一露水室中保持48小時,以使抱子發芽及使葉子感染。然後,植物移至設定於22℃之一生長室以供疾病發展。殺真菌劑之調配、施用及於經噴灑之葉子上的疾病評估係依循範例A中所述之程序。
Claims (19)
- 一種具化學式I之化合物,
- 如請求項1之化合物,其中,X及Y係氫。
- 如請求項2之化合物,其中,R1係烷基、芳基,或醯基,每一者選擇性地以0、1,或多數個R6取代。
- 如請求項2之化合物,其中,R2係選自-(CH2)nR8,其中,n係0與4間之整數,且R8係氫或烷基,其係選擇性地以0、1,或多數個R6取代。
- 如請求項1之化合物,其中,X係C(O)R3且Y係氫。
- 如請求項5之化合物,其中,R1係選自氫、烷基、芳基、醯基,或矽烷基,每一者係以0、1,或多數個R6取代。
- 如請求項5之化合物,其中,R2係選自-(CH2)nR8,其中,n係0與4間之整數,且R8係氫或烷基,其係選擇性地以0、1,或多數個R6取代。
- 如請求項1之化合物,其中,X係氫且Y係Q。
- 如請求項8之化合物,其中,R1係選自烷基、芳基,或醯基,每一者選擇性地以0、1,或多數個R6取代。
- 如請求項8之化合物,其中,R2係選自-(CH2)nR8,其中,n係0與4間之整數,且R8係氫或烷基,其係選擇性地以0、1,或多數個R6取代。
- 如請求項9之化合物,其中,R4係氫。
- 如請求項9之化合物,其中,R4係-C(O)R5或-CH2OC(O)R5。
- 如請求項12之化合物,其中,R5係選自烷基或烷氧基,每一者係以0、1,或多數個R6取代。
- 如請求項13之化合物,其中,R5係選自-CH3或-CH(CH3)2。
- 一種用於控制真菌病原體之組成物,包含至少一如請求項1-14之化合物,及一植物學可接受之載劑材料。
- 一種用於控制真菌病原體之組成物,包含至少一如請求項1-14之化合物與其它殺蟲劑之混合物,該等殺蟲劑包括殺真菌劑、殺昆蟲劑、殺棉蟲劑、殺蟎劑、殺節肢動物劑、殺細菌劑,及此等之組合。
- 如請求項15-16之組成物,其中,該真菌病原體係小麥葉斑病(禾生球腔菌(Mycosphaerella graminicola);無性態:枯葉病菌(Zymoseptoria tritici))、小麥葉锈病(小麥葉锈菌(Puccinia triticina))、小麥條銹病(條形扁菌(Puccinia striiformis))、蘋果結痂(蘋果黑星菌(Venturia inaequalis))、葡萄藤白粉病(葡萄白粉病菌(Uncinula necator))、大麥雲紋病(大麥雲紋病菌(Rhynchosporium secalis))、稻瘟病(稻熱病菌(Magnaporthe grisea))、大豆銹病(豆薯層銹菌(Phakopsora pachyrhizi))、小麥稃枯病(子囊菌(Leptosphaeria nodorum))、小麥白粉病(小麥白粉菌(Blumeria graminis f.sp.tritici))、大麥白粉病(大麥 白粉菌(Blumeria graminis f.sp.hordei))、瓜類白粉病(二孢白粉菌(Erysiphe cichoracearum))、瓜類炭疽病(胡瓜炭疽病菌(Glomerella lagenarium))、甜菜葉斑(甜菜生尾孢菌(Cercospora beticola))、蕃茄早枯萎病(索蘭尼鏈格孢(Alternaria solani)),及大麥斑枯(禾旋孢腔菌(Cochliobolus sativus))之一者。
- 如請求項17之組成物,其中,該真菌病原體係小麥葉斑病(枯葉病菌(Zymoseptoria tritici))、小麥葉锈病(小麥葉锈菌(Puccinia triticina)),及大豆銹病(豆薯層銹菌(Phakopsora pachyrhizi))。
- 一種用於控制及預防在植物上的真菌攻擊之方法,該方法包含下述步驟:使一殺真菌有效量之如請求項1-14之化合物中之至少一者或如請求項15-16之組成物中之至少一者施用至下列中之至少一者:該植物、鄰近該植物之一區域、適於支持該植物生長之土壤、該植物之一根,及該植物之葉子。
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US (1) | US20170334934A1 (zh) |
EP (1) | EP3212628A4 (zh) |
CN (1) | CN107074799A (zh) |
BR (1) | BR112017007825A2 (zh) |
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CA2374995C (en) * | 1999-07-20 | 2010-12-07 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
AR037328A1 (es) * | 2001-10-23 | 2004-11-03 | Dow Agrosciences Llc | Compuesto de [7-bencil-2,6-dioxo-1,5-dioxonan-3-il]-4-metoxipiridin-2-carboxamida, composicion que lo comprende y metodo que lo utiliza |
CA2818925A1 (en) * | 2010-11-24 | 2012-05-31 | Stemergie Biotechnology Sa | Inhibitors of the activity of complex iii of the mitochondrial electron transport chain and use thereof for treating diseases |
US8785479B2 (en) * | 2012-05-07 | 2014-07-22 | Dow Agrosciences, Llc. | Macrocyclic picolinamides as fungicides |
PL2847188T3 (pl) * | 2012-05-07 | 2017-07-31 | Dow Agrosciences Llc | Makrocykliczne pikolinamidy jako fungicydy |
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2015
- 2015-10-22 EP EP15855581.3A patent/EP3212628A4/en not_active Withdrawn
- 2015-10-22 CN CN201580055923.XA patent/CN107074799A/zh active Pending
- 2015-10-22 BR BR112017007825A patent/BR112017007825A2/pt not_active Application Discontinuation
- 2015-10-22 US US15/522,132 patent/US20170334934A1/en not_active Abandoned
- 2015-10-22 WO PCT/US2015/056905 patent/WO2016069370A1/en active Application Filing
- 2015-10-27 TW TW104135243A patent/TW201617339A/zh unknown
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BR112017007825A2 (pt) | 2017-12-26 |
EP3212628A1 (en) | 2017-09-06 |
US20170334934A1 (en) | 2017-11-23 |
EP3212628A4 (en) | 2018-04-04 |
WO2016069370A1 (en) | 2016-05-06 |
CN107074799A (zh) | 2017-08-18 |
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