TW201607929A - N-環烷基-n-{[2-(1-經取代環烷基)苯基]亞甲基}-(硫代)甲醯胺衍生物 - Google Patents
N-環烷基-n-{[2-(1-經取代環烷基)苯基]亞甲基}-(硫代)甲醯胺衍生物 Download PDFInfo
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- TW201607929A TW201607929A TW103142233A TW103142233A TW201607929A TW 201607929 A TW201607929 A TW 201607929A TW 103142233 A TW103142233 A TW 103142233A TW 103142233 A TW103142233 A TW 103142233A TW 201607929 A TW201607929 A TW 201607929A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- A—HUMAN NECESSITIES
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Abstract
本發明係關於殺真菌N-環烷基-N-{[2-(1-經取代之環烷基)苯基]亞甲基}羧醯胺衍生物及其硫代羰基衍生物,其製備方法及用於其製備之中間化合物,其作為殺真菌劑(特定言之呈殺真菌組合物形式之殺真菌劑)之用途及使用此等化合物或其組合物控制植物之植物病原性真菌的方法。
Description
本發明係關於殺真菌N-環烷基-N-{[2-(1-經取代之環烷基)苯基]亞甲基}羧醯胺衍生物及其硫羰基衍生物,其製備方法及用於其製備之中間化合物,其作為殺真菌劑(特定言之呈殺真菌組合物形式)之用途及使用此等化合物或其組合物控制植物之植物病原性真菌的方法。
在國際專利申請案WO-2007/087906中,某些N-環烷基-N-苯甲基-羧醯胺一般涵蓋在眾多下式化合物之廣泛揭示中:
其中A表示碳連接之部分飽和或不飽和5員雜環基,Z1表示經取代或未經取代之C3-C7環烷基,n等於1至5且X可表示多種取代基,其中存在未經取代之C3-C7環烷基。然而,此文件中無關於X可表示經取代之C3-C7環烷基的任何此類衍生物之明確揭示內容或建議供選擇。
在國際專利申請案WO-2009/016220中,某些N-環烷基-N-苯甲基-硫代羧醯胺一般涵蓋在眾多下式化合物之廣泛揭示中:
其中A表示碳連接之部分飽和或不飽和5員雜環基,T可表示S,Z1表示經取代或未經取代之C3-C7環烷基,n等於1至5且X可表示多種取代基,其中存在未經取代之C3-C7環烷基。然而,此文件中無關於X可表示經取代之C3-C7環烷基的任何此類衍生物之明確揭示內容或建議供選擇。
在國際專利申請案WO-2010/130767中,某些N-環烷基-N-苯甲基-羧醯胺或硫代羧醯胺一般涵蓋在眾多下式化合物之廣泛揭示中:
其中X1及X2表示氟或氯原子,T可表示O或S,Z1表示經取代或未經取代之環丙基,Y可表示CR5且各取代基Ri(i為1至5之整數)可獨立地表示多種取代基,其中存在經取代或未經取代之C3-C7環烷基。然而,此文件中無關於Ri(i為1至5之整數)可表示經取代之C3-C7環烷基的任何此類衍生物之明確揭示內容。
在國際專利申請案WO-2012/052490中,某些N-環烷基-N-苯甲基-羧醯胺或硫代羧醯胺一般涵蓋在眾多下式化合物之廣泛揭示中:
其中X1及X2表示氟或氯原子,T可表示O
或S,Z1可表示經取代或未經取代之C4-C7環烷基,Y可表示CR5且各取代基Ri(i為1至5之整數)可獨立地表示多種取代基,其中存在經取代或未經取代之C3-C7環烷基。然而,此文件中無關於Ri(i為1至5之整數)可表示經取代之C4-C7環烷基的任何此類衍生物之明確揭示內
容。
因此,本發明提供式(I)之N-環烷基-N-{[2-(1-經取代之環烷基)苯基]-亞甲基}(硫代)羧醯胺
其中●A表示碳連接之不飽和或部分飽和5員雜環基,其可經多達四個可相同或不同之基團R取代,其限制條件為A不表示3-(二鹵代甲基)-5-鹵代-1-甲基-1H-吡唑-4-基,其中該等鹵代原子可獨立地表示氟或氯原子;●T表示O或S;●n表示0、1、2、3或4;●m表示0、1、2、3、4、5或6;●p表示1、2、3、4或5;●Z1表示未經取代之C3-C7環烷基或經多達10個原子或基團取代之C3-C7環烷基,該等原子或基團可相同或不同且可選自由以下組成之群:鹵素原子、氰基、C1-C8烷基、包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷基、C1-C8烷氧基、包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷氧基、C1-C8烷氧羰基、包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷氧羰基、C1-C8烷基胺基羰基及二-C1-C8烷基胺基羰基;●Z2及Z3可相同或不同且表示氫原子;經取代或未經取代之C1-C8烷基;經取代或未經取代之C2-C8烯基;經取代或未經取代之C2-C8
炔基;氰基;異腈;硝基;鹵素原子;經取代或未經取代之C1-C8烷氧基;經取代或未經取代之C2-C8烯基氧基;經取代或未經取代之C2-C8炔基氧基;經取代或未經取代之C3-C7環烷基;經取代或未經取代之C1-C8烷基硫基;經取代或未經取代之C1-C8烷基磺醯基;經取代或未經取代之C1-C8烷基亞磺醯基;胺基;經取代或未經取代之C1-C8烷基胺基;經取代或未經取代之二-C1-C8烷基胺基;經取代或未經取代之C1-C8烷氧羰基;經取代或未經取代之C1-C8烷基胺甲醯基;經取代或未經取代之二-C1-C8烷基胺甲醯基;或經取代或未經取代之N-C1-C8烷基-C1-C8烷氧基-胺甲醯基;或●Z2及Z3連同其所連接之碳原子一起可形成經取代或未經取代之C3-C7環烷基;●Z4表示鹵素原子;羥基;氰基;經取代或未經取代之C1-C8烷基;具有1至5個鹵素原子之C1-C8鹵代烷基;經取代或未經取代之C2-C8烯基;具有1至5個鹵素原子之C2-C8鹵代烯基;經取代或未經取代之C2-C8炔基;具有1至5個鹵素原子之C2-C8鹵代炔基;經取代或未經取代之C1-C8烷氧基;具有1至5個鹵素原子之C1-C8鹵代烷氧基;經取代或未經取代之C1-C8烷基硫基;甲醯基;經取代或未經取代之C1-C8烷基羰基;羧基;或經取代或未經取代之C1-C8烷氧羰基;X獨立地表示鹵素原子;硝基;氰基;異腈;羥基;胺基;硫基;五氟-λ6-硫基;甲醯基;甲醯基氧基;甲醯基胺基;經取代或未經取代之(羥基亞胺基)-C1-C8烷基;經取代或未經取代之(C1-C8烷氧基亞胺基)-C1-C8烷基;經取代或未經取代之(C2-C8烯基氧基亞胺基)-C1-C8烷基;經取代或未經取代之(C2-C8炔基氧基亞胺基)-C1-C8烷基;經取代或未經取代之(苯甲基氧基亞胺基)-C1-C8烷基;羧基;胺甲醯基;N-羥基胺甲醯基;胺基甲酸酯基;經取代或未經取代之C1-C8烷基;具有1至9個鹵素原子之C1-C8鹵代烷基;經取代或未經取代之C2-C8烯基;具有1
至9個鹵素原子之C2-C8鹵代烯基;經取代或未經取代之C2-C8炔基;具有1至9個鹵素原子之C2-C8鹵代炔基;經取代或未經取代之C1-C8烷氧基;具有1至9個鹵素原子之C1-C8鹵代烷氧基;經取代或未經取代之C1-C8烷基硫基;具有1至9個鹵素原子之C1-C8鹵代烷基硫基;經取代或未經取代之C1-C8烷基亞磺醯基;具有1至9個鹵素原子之C1-C8鹵代烷基亞磺醯基;經取代或未經取代之C1-C8烷基磺醯基;具有1至9個鹵素原子之C1-C8鹵代烷基磺醯基;經取代或未經取代之C1-C8烷基胺基;經取代或未經取代之二-C1-C8烷基胺基;經取代或未經取代之C2-C8烯基氧基;具有1至9個鹵素原子之C2-C8鹵代烯基氧基;經取代或未經取代之C3-C8炔基氧基;具有1至9個鹵素原子之C2-C8鹵代炔基氧基;經取代或未經取代之C3-C7環烷基;具有1至9個鹵素原子之C3-C7鹵代環烷基;經取代或未經取代之(C3-C7環烷基)-C1-C8烷基;經取代或未經取代之C4-C7-環烯基;具有1至9個鹵素原子之C4-C7鹵代環烯基;經取代或未經取代之(C3-C7環烷基)-C2-C8烯基;經取代或未經取代之(C3-C7環烷基)-C2-C8炔基;經取代或未經取代之雙環[2.2.1]庚烷基;經取代或未經取代之雙環[2.2.1]庚烯基;經取代或未經取代之三(C1-C8)烷基矽烷基;經取代或未經取代之三(C1-C8)烷基矽烷基-C1-C8烷基;經取代或未經取代之C1-C8烷基羰基;具有1至9個鹵素原子之C1-C8鹵代烷基羰基;經取代或未經取代之C1-C8烷基羰基氧基;具有1至9個鹵素原子之C1-C8鹵代烷基羰基氧基;經取代或未經取代之C1-C8烷基羰基胺基;具有1至9個鹵素原子之C1-C8鹵代烷基羰基胺基;經取代或未經取代之C1-C8烷氧羰基;具有1至9個鹵素原子之C1-C8鹵代烷氧羰基;經取代或未經取代之C1-C8烷基氧基羰基氧基;具有1至9個鹵素原子之C1-C8鹵代烷氧羰基氧基;經取代或未經取代之C1-C8烷基胺甲醯基;經取代或未經取代之二-C1-C8烷基胺甲醯基;經取代或未經取代之C1-C8烷基胺基羰基氧基;經取代或未經取代之二-C1-C8
烷基胺基羰基氧基;經取代或未經取代之N-(C1-C8烷基)羥基胺甲醯基;經取代或未經取代之C1-C8烷氧基胺甲醯基;經取代或未經取代之N-(C1-C8烷基)-C1-C8烷氧基胺甲醯基;可經多達6個可相同或不同之基團Q取代之芳基;可經多達6個可相同或不同之基團Q取代之C1-C8芳基烷基;可經多達6個可相同或不同之基團Q取代之C2-C8芳基烯基;可經多達6個可相同或不同之基團Q取代之C2-C8芳基炔基;可經多達6個可相同或不同之基團Q取代之芳基氧基;可經多達6個可相同或不同之基團Q取代之芳基硫基;可經多達6個可相同或不同之基團Q取代之芳基胺基;可經多達6個可相同或不同之基團Q取代之C1-C8芳基烷基氧基;可經多達6個可相同或不同之基團Q取代之C1-C8芳基烷基硫基;可經多達6個可相同或不同之基團Q取代之C1-C8芳基烷基胺基;可經多達6個可相同或不同之基團Q取代之C1-C8雜芳基烷基;可經多達4個基團Q取代之雜芳基;或可經多達4個基團Q取代之雜芳基氧基;或●Z4及其鄰接取代基X與其所連接之碳原子一起可形成經取代或未經取代之C4-C7環烷基;●Y獨立地表示鹵素原子;C1-C8烷基;具有1至9個鹵素原子之C1-C8鹵代烷基;經取代或未經取代之C1-C8烷氧基;具有1至9個鹵素原子之C1-C8鹵代烷氧基;經取代或未經取代之C1-C8烷基硫基;具有1至9個鹵素原子之C1-C8鹵代烷基硫基;或經取代或未經取代之C1-C8烷氧羰基;Q獨立地表示鹵素原子、氰基、硝基、經取代或未經取代之C1-C8烷基、包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷基、經取代或未經取代之C1-C8烷氧基、包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷氧基、經取代或未經取代之C1-C8烷基硫基、包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷基硫基、經取代或未經取代之三(C1-C8)烷基矽烷基、經取代或未經取代之三(C1-C8)烷
基矽烷基-C1-C8烷基、經取代或未經取代之(C1-C8烷氧基亞胺基)-C1-C8烷基或經取代或未經取代之(苯甲基氧基亞胺基)-C1-C8烷基;●R獨立地表示氫原子;鹵素原子;硝基;氰基;羥基;胺基;硫基;五氟-λ6-硫基;經取代或未經取代之(C1-C8烷氧基亞胺基)-C1-C8烷基;經取代或未經取代之(苯甲基氧基亞胺基)-C1-C8烷基;經取代或未經取代之C1-C8烷基;具有1至9個鹵素原子之C1-C8鹵代烷基;經取代或未經取代之C2-C8烯基;具有1至9個鹵素原子之C2-C8鹵代烯基;經取代或未經取代之C2-C8炔基;具有1至9個鹵素原子之C2-C8鹵代炔基;經取代或未經取代之C1-C8烷氧基;具有1至9個鹵素原子之C1-C8鹵代烷氧基;經取代或未經取代之C1-C8烷基硫基;具有1至9個鹵素原子之C1-C8鹵代烷基硫基;經取代或未經取代之C1-C8烷基亞磺醯基;具有1至9個鹵素原子之C1-C8鹵代烷基亞磺醯基;經取代或未經取代之C1-C8烷基磺醯基;具有1至9個鹵素原子之C1-C8鹵代烷基磺醯基;經取代或未經取代之C1-C8烷基胺基;經取代或未經取代之二-C1-C8烷基胺基;經取代或未經取代之C2-C8烯基氧基;經取代或未經取代之C3-C8炔基氧基;經取代或未經取代之C3-C7環烷基;具有1至9個鹵素原子之C3-C7鹵代環烷基;經取代或未經取代之三(C1-C8)烷基矽烷基;經取代或未經取代之C1-C8烷基羰基;具有1至9個鹵素原子之C1-C8鹵代烷基羰基;經取代或未經取代之C1-C8烷氧羰基;具有1至9個鹵素原子之C1-C8鹵代烷氧羰基;經取代或未經取代之C1-C8烷基胺甲醯基;經取代或未經取代之二-C1-C8烷基胺甲醯基;苯氧基;苯基硫基;苯基胺基;苯甲基氧基;苯甲基硫基;或苯甲基胺基;以及其鹽、N-氧化物、金屬錯合物、類金屬複合物及其光學活性異構體或幾何異構體。
除非另外指示,否則根據本發明經取代之基團或取代基可經以下基團或原子中之一或多者取代:鹵素原子;硝基;羥基;氰基;異
腈;胺基;硫基;五氟-λ6-硫基;甲醯基;甲醯基氧基;甲醯基胺基;胺甲醯基;N-羥基胺甲醯基;胺基甲酸酯基;(羥基亞胺基)-C1-C6烷基;C1-C8烷基;三(C1-C8烷基)矽烷基;C3-C8環烷基;具有1至5個鹵素原子之C1-C8鹵代烷基;具有1至5個鹵素原子之C3-C8鹵代環烷基;C2-C8烯基;C2-C8炔基;C2-C8烯基氧基;C2-C8炔基氧基;C1-C8烷基胺基;二-C1-C8烷基胺基;C1-C8烷氧基;具有1至5個鹵素原子之C1-C8鹵代烷氧基;C1-C8烷基硫基;具有1至5個鹵素原子之C1-C8鹵代烷基硫基;C2-C8烯基氧基;具有1至5個鹵素原子之C2-C8鹵代烯基氧基;C3-C8炔基氧基;具有1至5個鹵素原子之C3-C8鹵代炔基氧基;C1-C8烷基羰基;具有1至5個鹵素原子之C1-C8鹵代烷基羰基;C1-C8烷基胺甲醯基;二-C1-C8烷基胺甲醯基;N-C1-C8烷基氧基胺甲醯基;C1-C8烷氧基胺甲醯基;N-C1-C8烷基-C1-C8烷氧基胺甲醯基;C1-C8烷氧羰基;具有1至5個鹵素原子之C1-C8鹵代烷氧羰基;C1-C8烷基羰基氧基;具有1至5個鹵素原子之C1-C8鹵代烷基羰基氧基;C1-C8烷基羰基胺基;具有1至5個鹵素原子之C1-C8鹵代烷基羰基胺基;C1-C8烷基胺基羰基氧基;二-C1-C8烷基胺基羰基氧基;C1-C8烷基氧基羰基氧基;C1-C8烷基硫基;具有1至5個鹵素原子之C1-C8鹵代烷基硫基;C1-C8烷基亞磺醯基;具有1至5個鹵素原子之C1-C8鹵代烷基亞磺醯基;C1-C8烷基磺醯基;具有1至5個鹵素原子之C1-C8鹵代烷基磺醯基;C1-C8烷基胺基胺磺醯基;二-C1-C8烷基胺基胺磺醯基;(C1-C6烷氧基亞胺基)-C1-C6-烷基;(C1-C6-烯基氧基亞胺基)-C1-C6-烷基;(C1-C6炔基氧基亞胺基)-C1-C6-烷基;2-側氧基吡咯啶-1-基;(苯甲基氧基亞胺基)-C1-C6-烷基;C1-C8烷氧基烷基;具有1至5個鹵素原子之C1-C8鹵代烷氧基烷基;苯甲基氧基;苯甲基硫基;苯甲基胺基;芳基氧基;芳基硫基或芳基胺基。
根據本發明,以下通用術語一般與以下含義一起使用:
●鹵素意謂氟、氯、溴或碘,羧基意謂-C(=O)OH;羰基意謂-C(=O)-;胺甲醯基意謂-C(=O)NH2;N-羥基胺甲醯基意謂-C(=O)NHOH;SO表示亞碸基;SO2表示碸基;雜原子意謂硫、氮或氧;亞甲基意謂二基-CH2-;
●烷基、烯基及炔基以及含有此等術語之部分可為直鏈或分支鏈的;
●鹵化基團(尤其鹵烷基、鹵烷氧基及環烷基)可包含多達九個相同或不同之鹵素原子;
●術語「芳基」意謂苯基或萘基;
●術語「雜芳基」意謂飽和、部分飽和或不飽和單環或稠合雙環3、4、5、6、7、8、9、10員環,其包含1至4個選自由N、O及S組成之清單的雜原子;
●在胺基或任何其他含有胺基之基團的胺基部分經兩個可相同或不同之取代基取代的情況中,兩個取代基連同其所連接之氮原子一起可形式雜環基,較佳5至7員雜環基,其可經取代或可包括其他雜原子,例如(N-嗎啉基)或哌啶基。
●在本發明化合物可以互變異構形式存在之情況下,此類化合物在上文及下文中亦應理解為在適用情況下包括對應互變異構形式,甚至在各種情況下未特定提及此等互變異構形式時亦如此。
視化合物中之不對稱中心數而定,本發明化合物中之任一者可以一或多種光學或對掌性異構體形式存在。因此,本發明同樣關於所
有光學異構體及其外消旋或非外消旋混合物(術語「非外消旋」表示呈不同比例之對映異構體之混合物)及呈所有比例之所有可能立體異構體之混合物。非對映異構體及/或光學異構體可根據一般技術者本身已知之方法分離。
視化合物中之雙鍵數而定,本發明化合物中之任一者亦可以一或多種幾何異構體形式存在。因此,本發明同樣關於所有幾何異構體及呈所有比例之所有可能混合物。幾何異構體可根據一般技術者本身已知之通用方法分離。
視鏈或環之取代基之相對位置(同側/反側或順式/反式或內型/外型)而定,本發明化合物中之任一者亦可以一或多種幾何異構體形式存在。因此,本發明同樣係關於所有同側/反側(或順式/反式或內型/外型)異構體,且關於呈各種比例之所有可能的同側/反側(或順式/反式或內型/外型)混合物。同側/反側(或順式/反式或內型/外型)異構體可根據一般技術者本身已知的通用方法來分離。
本發明之較佳化合物為式(I)化合物,其中A係選自由以下組成之清單:-式(A1)之雜環
其中:R1至R3可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;
-式(A2)雜環
其中:R4至R6可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;-式(A3)之雜環
其中:R7表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;R8表示氫原子或經取代或未經取代之C1-C5烷基;-式(A4)之雜環
其中:R9至R11可相同或不同且表示氫原子;鹵素原子;經取代或未經
取代之C1-C5烷基;胺基;經取代或未經取代之C1-C5烷氧基;經取代或未經取代之C1-C5烷基硫基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;-式(A5)之雜環
其中:R12及R13可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;胺基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;R14表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;胺基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;-式(A6)之雜環
其中:R15表示氫原子;鹵素原子;氰基;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基或包含多達9個可相同或不同之鹵素原子
之C1-C5鹵代烷基;R16及R18可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷氧羰基;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R17表示氫原子或經取代或未經取代之C1-C5烷基;-式(A7)之雜環
其中:R19表示氫原子或C1-C5烷基R20至R22可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A8)之雜環
其中:R23表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R24表示氫原子或經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A9)之雜環
其中:R25表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R26表示氫原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A10)之雜環
其中:R27表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R28表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;胺基;經取代或未經取代之C1-C5烷基胺基或經取代或未經取代之二(C1-C5烷基)胺基;-式(A11)之雜環
其中:R29表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;包含多達9個可相同或不同之鹵素原
子之C1-C5鹵代烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R30表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;胺基;經取代或未經取代之C1-C5烷基胺基或經取代或未經取代之二(C1-C5烷基)胺基;-式(A12)之雜環
其中:R31表示氫原子或經取代或未經取代之C1-C5烷基R32表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R33表示氫原子;鹵素原子;硝基;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A13)之雜環
其中:R34表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經
取代或未經取代之C3-C5環烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基;經取代或未經取代之C2-C5炔基氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;R35表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;氰基;經取代或未經取代之C1-C5烷氧基;經取代或未經取代之C1-C5烷基硫基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;胺基;經取代或未經取代之C1-C5烷基胺基或經取代或未經取代之二(C1-C5烷基)胺基;R36表示氫原子或經取代或未經取代之C1-C5烷基;其限制條件為當R34同時表示二氟甲基或二氯甲基且R36同時表示甲基時,R35不表示氟或氯原子;-式(A14)之雜環
其中:R37及R38可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基或經取代或未經取代之C1-C5烷基硫基;R39表示氫原子或經取代或未經取代之C1-C5烷基;-式(A15)之雜環
其中:R40及R41可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A16)之雜環
其中:R42及R43可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基或胺基;-式(A17)之雜環
其中:R44及R45可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A18)之雜環
其中:R47表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R46表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基或經取代或未經取代之C1-C5烷基硫基;-式(A19)之雜環
其中:R49及R48可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A20)之雜環
其中:R50及R51可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經取代或未經取代之C1-C5烷氧基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;-式(A21)之雜環
其中:R52表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基。
-式(A22)之雜環
其中:R53表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基。
-式(A23)之雜環
其中:R54及R56可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R55表示氫原子或經取代或未經取代之C1-C5烷基;-式(A24)之雜環
其中:R57及R59可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R58表示氫原子或經取代或未經取代之C1-C5烷基;-式(A25)之雜環
其中:R60及R61可相同或不同且表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;R62表示氫原子或經取代或未經取代之C1-C5烷基;-式(A26)之雜環
其中:R65表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;經取代或未經取代之C3-C5環烷基;包含多達9個可相同或不同之鹵素原
子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基;經取代或未經取代之C2-C5炔基氧基或包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;R63表示氫原子;鹵素原子;經取代或未經取代之C1-C5烷基;氰基;經取代或未經取代之C1-C5烷氧基;經取代或未經取代之C1-C5烷基硫基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷氧基;胺基;經取代或未經取代之C1-C5烷基胺基或二(C1-C5烷基)胺基;R64表示氫原子或經取代或未經取代之C1-C5烷基。
本發明之化合物更佳為式(I)化合物,其中A係選自由如本文所定義之A2;A3;A5;A6;A10及A13組成之清單。
甚至更佳的本發明化合物為式(I)化合物,其中A表示A13,其中R34表示經取代或未經取代之C1-C5烷基、包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基;R35表示氫原子或鹵素原子且R36表示經取代或未經取代之C1-C5烷基。
本發明之化合物甚至更佳為式(I)化合物,其中A表示A13,其中R34表示C1-C5烷基、包含多達3個可相同或不同之鹵素原子之C1-C5鹵代烷基;R35表示氫原子;氯原子;或氟原子;且R36表示甲基。
本發明之其他較佳化合物為式(I)化合物,其中T表示O。
本發明之其他較佳化合物為式(I)化合物,其中Z1表示經取代或未經取代之環丙基。
本發明之其他更佳化合物為式(I)化合物,其中Z1表示未經取代之環丙基或C1-C5烷基環丙基。
本發明之其他甚至更佳化合物為式(I)化合物,其中Z1表示未經取代之環丙基。
本發明之其他甚至更佳化合物為式(I)化合物,其中Z1表示甲基
環丙基。
本發明之其他較佳化合物為式(I)化合物,其中Z2及Z3獨立地表示氫原子或甲基。
本發明之其他更佳化合物為式(I)化合物,其中Z2表示氫原子且Z3表示氫原子或甲基。
本發明之其他較佳化合物為式(I)化合物,其中n表示0、1或2。
本發明之其他較佳化合物為式(I)化合物,其中m表示0、1、2、3或4,較佳0、1或2。
本發明之其他較佳化合物為式(I)化合物,其中p表示1、3或4。
本發明之其他更佳化合物為式(I)化合物,其中p表示1。
本發明之其他較佳化合物為式(I)化合物,其中Z4表示鹵素、經取代或未經取代之C1-C4烷基、具有1至3個鹵素原子之C1-C4鹵代烷基、經取代或未經取代之C1-C4烷基氧基、經取代或未經取代之環丙基、經取代或未經取代之C2-C4烯基或經取代或未經取代之C2-C4炔基。
本發明之其他更佳化合物為式(I)化合物,其中Z4表示氯、甲基、乙基、丙基、異丙基、異丁基、環丙基、甲氧基、甲氧基甲基、二氟甲基、三氟甲基或乙炔基。
本發明之其他較佳化合物為式(I)化合物,其中X獨立地表示鹵素原子;經取代或未經取代之C1-C8烷基;包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷基;經取代或未經取代之C2-C8烯基;經取代或未經取代之C5-C7環烯基;經取代或未經取代之C3-C7環烷基;三(C1-C8烷基)矽烷基;經取代或未經取代之C1-C8烷氧基;經取代或未經取代之C1-C8烷基硫基;經取代或未經取代之苯基;經取代或未經取代之噻吩基或經取代或未經取代之呋喃基。
本發明之其他較佳化合物為式(I)化合物,其中Y獨立地表示鹵素
或經取代或未經取代之C1-C8烷基。
關於本發明化合物之取代基之上述偏好可以各種方式組合。因此較佳特徵之此等組合提供本發明化合物之子類。本發明之較佳化合物之此類子類之實例為:-A之較佳特徵與T、Z1至Z4、n、m、p、X及Y之較佳特徵;-T之較佳特徵與A、Z1至Z4、n、m、p、X及Y之較佳特徵;-Z1之較佳特徵與A、T、Z2至Z4、n、m、p、X及Y之較佳特徵;-Z2之較佳特徵與A、T、Z1、Z3至Z4、n、m、p、X及Y之較佳特徵;-Z3之較佳特徵與A、T、Z1至Z2、Z4、n、m、p、X及Y之較佳特徵;-Z4之較佳特徵與A、T、Z1至Z3、n、m、p、X及Y之較佳特徵;-n之較佳特徵與A、T、Z1至Z4、m、p、X及Y之較佳特徵;-m之較佳特徵與A、T、Z1至Z4、n、p、X及Y之較佳特徵;-p之較佳特徵與A、T、Z1至Z4、n、m、X及Y之較佳特徵;-X之較佳特徵與A、T、Z1至Z4、n、m、p及Y之較佳特徵;-Y之較佳特徵與A、T、Z1至Z4、n、m、p及X之較佳特徵。
在本發明化合物之取代基之較佳特徵的此等組合中,該等較佳特徵亦可選自A、T、Z1至Z4、n、m、p、X及Y中之每一者之更佳特徵以便形成本發明化合物之最佳子類。
本發明亦係關於一種用於製備式(I)化合物之方法。
因此,根據本發明之另一態樣,提供一種製備如本文所定義且其中T表示O之式(I)化合物之方法P1,且該方法包含使式(II)之胺或其鹽中之一者:
其中Z1、Z2、Z3、Z4、n、m、p、X及Y如本文所定義;與式(III)之羧酸衍生物:
其中A如本文所定義且U1表示選自由以下組成之清單的離去基:鹵素原子、羥基、-ORa、-OC(=O)Ra(Ra為經取代或未經取代之C1-C6烷基、經取代或未經取代之C1-C6鹵烷基、苯甲基、4-甲氧基苯甲基或五氟苯基),或式O-C(=O)A之基團;必要時,在催化劑存在下,且在U1表示羥基之情況下在縮合劑存在下,且在U1表示鹵素原子之情況下在酸黏合劑存在下反應。
式(II)之N-取代之胺衍生物為已知或可藉由已知方法製備,諸如式(IV)之醛:
其中Z4、n、m、p、W及Y如本文所定義,或酮的還原胺化(Bioorganics and Medicinal Chemistry Letters(2006),16,2014),或亞胺之還原(Tetrahedron(2005),61,11689),或式(V)之鹵代苯甲基衍生物之鹵素的親核取代:
其中U2為鹵素,較佳氯、溴及碘,且Z4、n、m、p、W及Y如本文所定義,或甲磺酸酯或甲苯磺酸酯之取代(Journal of Medicinal Chemistry(2002),45,3887)。
式(III)之羧酸衍生物為已知的或可藉由已知方法製備。
在U1表示羥基之情況中,根據本發明之方法P1在縮合劑存在下進行。適合縮合劑可選自由以下組成之非限制性清單:酸鹵化物形成劑,諸如光氣、三溴化磷、三氯化磷、五氯化磷、三氯氧磷或亞硫醯氯;酐形成劑,諸如氯甲酸乙酯、氯甲酸甲酯、氯甲酸異丙酯、氯甲酸異丁酯或甲磺醯氯;碳化二亞胺,諸如N,N'-二環己基碳化二亞胺(DCC)或其他慣用縮合劑,諸如五氧化磷、聚磷酸、N,N'-羰基-二咪唑、2-乙氧基-N-乙氧羰基-1,2-二氫喹啉(EEDQ)、三苯膦/四氯甲烷、水合氯化4-(4,6-二甲氧基[1.3.5]-三嗪-2-基)-4-甲基嗎啉鎓、六氟磷酸溴-三吡咯啶鏻或丙烷膦酸酐(T3P)。
本發明之方法P1可在催化劑存在下進行。適合催化劑可選自由以下組成之清單:N,N-二甲基吡啶-4-胺、1-羥基-苯丙三唑或N,N-二甲基甲醯胺。
在U1表示鹵素原子之情況中,本發明之方法P1在酸黏合劑存在下進行。用於進行本發明之方法P1之適合酸黏合劑在各種情況下為慣用於此類反應之所有無機及有機鹼。較佳使用鹼土金屬、鹼金屬氫化物、鹼金屬氫氧化物或鹼金屬醇鹽,諸如氫氧化鈉、氫化鈉、氫氧化鈣、氫氧化鉀、第三丁醇鉀,或其他氫氧化銨;鹼金屬碳酸鹽,諸如
碳酸銫、碳酸鈉、碳酸鉀、碳酸氫鉀、碳酸氫鈉;鹼金屬或鹼土金屬乙酸鹽,諸如乙酸鈉、乙酸鉀、乙酸鈣;亦及三級胺,諸如三甲胺、三乙胺、二異丙基乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基吡啶-4-胺、二氮雜雙環辛烷(DABCO)、二氮雜雙環壬烯(DBN)或二氮雜雙環十一烯(DBU)。
亦有可能在無額外縮合劑存在之情況下進行或採用過量胺組分以便其同時充當酸黏合劑。
用於進行本發明之方法P1之適合溶劑可為慣用惰性有機溶劑。較佳為使用視情況經鹵化之脂族、脂環族或芳族烴,諸如石油醚、己烷、庚烷、環己烷、甲基環己烷、苯、甲苯、二甲苯或十氫萘;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,諸如乙醚、二異丙醚、甲基第三丁基醚、甲基第三戊基醚、二噁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,諸如乙腈、丙腈、正或異丁腈或苯甲腈;醯胺,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基甲醯苯胺、N-甲基吡咯啶酮或六甲基磷醯三胺;醇,諸如甲醇、乙醇、丙醇、異丙醇;酯,諸如乙酸甲酯或乙酸乙酯;亞碸,諸如二甲亞碸;或碸,諸如環丁碸。
當進行本發明方法P1時,式(II)之胺衍生物可以其鹽形式使用,諸如鹽酸鹽或任何其他適宜鹽。
當進行本發明之方法P1時,每莫耳式(III)之試劑可採用1莫耳或過量式(II)之胺衍生物及1至3莫耳酸黏合劑。
亦可採用其他比率之反應組分。藉由已知方法進行處理。
根據本發明之另一態樣,提供一種製備T表示S之式(I)化合物之第二方法P2,該方法以T表示O之式(I)化合物為起始物質且根據以下反應流程說明:
其中A、Z1、Z2、Z3、Z4、n、m、p、X及Y如本文所定義。
本發明之方法P2在硫化試劑存在下進行。
T表示O之起始式(I)醯胺衍生物可根據方法P1製備。
用於進行本發明之方法P2之適合硫化試劑可為硫(S)、氫硫酸(H2S)、硫化鈉(Na2S)、硫氫化鈉(NaHS)、三硫化硼(B2S3)、硫化雙(二乙基鋁)((AlEt2)2S)、硫化銨((NH4)2S)、五硫化磷(P2S5)、勞森試劑(Lawesson's reagent,2,4-雙(4-甲氧基苯基)-1,2,3,4-二硫雜二磷雜環丁烷2,4-二硫化物)或聚合物載體硫化試劑,諸如Journal of the Chemical Society,Perkin 1(2001),358中所述,視情況在催化量或化學計量或過量之鹼(諸如無機及有機鹼)存在下。較佳使用鹼金屬碳酸鹽,諸如碳酸鈉、碳酸鉀、碳酸氫鉀、碳酸氫鈉;雜環芳族鹼,諸如吡啶、甲基吡啶、二甲基吡啶、三甲基吡啶;及亦三級胺,諸如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基吡啶-4-胺或N-甲基-哌啶。
用於進行本發明之方法P2之適合溶劑可為慣用惰性有機溶劑。較佳使用視情況鹵化之脂族、脂環族或芳族烴,諸如石油醚、己烷、庚烷、環己烷、甲基環己烷、苯、甲苯、二甲苯或十氫萘;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,諸如乙醚、二異丙基醚、甲基第三丁基醚、甲基第三戊基醚、二噁烷、四氫呋喃、1,2-二甲氧基乙烷或1,2-二乙氧基乙烷;腈,諸如乙腈、丙
腈、正丁腈或異丁腈或苯甲腈;含硫溶劑,諸如環丁碸或二硫化碳。
當進行本發明之方法P2時,每莫耳醯胺反應物(I)可使用1莫耳或過量之硫化試劑之硫等效物及1至3莫耳鹼。
亦可採用其他比率之反應組分。藉由已知方法進行處理。
當進行本發明方法P1及P2時,反應溫度可在相對廣泛範圍內變化。一般而言,此等方法在0℃至200℃,較佳10℃至150℃之溫度下進行。控制本發明之方法之溫度的方式為使用微波技術。
本發明亦關於製備式IV化合物之方法(方法P3)。
其中U3定義為溴或碘,且Z4、n、m、p、X及Y如本文所定義。
藉由甲醯化反應,諸如與有機鋰或有機鎂試劑的鹵素-金屬交換,隨後依序添加親電試劑(例如N,N-二甲基甲醯胺(DMF))的反應順序,自通式(VI)化合物獲得通式(IV)化合物;參見例如Journal of the American Chemical Society,(2008),130(26),8481-8490。或者,鎂可用於自(VI)形成格林納試劑,其接著可用適當親電子試劑(諸如DMF)處理形成通式(IV)化合物(參見例如:Chemistry Letters,(2007),36(1),72-73)。
在適合有機金屬化合物或鎂存在下進行方法P3。較佳有機金屬化合物為有機鋰化合物(例如丁基鋰)或有機鎂化合物(例如氯化異丙基鎂或溴化異丙基鎂)。
方法P3較佳使用一或多種稀釋劑進行。適用於進行方法P3之溶
劑較佳為非質子溶劑(例如二噁烷、乙二醇二甲醚、烷烴、環烷烴、乙醚或四氫呋喃)。尤其較佳為乙醚或四氫哌喃。
進行方法P3時,反應溫度可在相對廣泛範圍內變化。在鹵素-金屬交換反應的情況中,所採用之溫度一般為-120℃至150℃,較佳溫度為-120℃至60℃,最佳-120℃至70℃。在添加諸如DMF之親電子試劑之後,較佳在-80℃至50℃下進行處理。
為了進行方法P3,每莫耳式(VI)化合物使用一般1至2莫耳,較佳1莫耳有機金屬化合物及親電子試劑。
本發明亦關於製備式V化合物之方法(方法P4)。
其中U2定義為鹵素,較佳氯、溴或碘,且Z4、n、m、p、X及Y如本文所定義。
藉由甲基之基團鹵化自通式(VII)化合物獲得通式(V)化合物;參見例如WO2008/016239、WO2013/051632。
在適合鹵化劑(例如N-氯丁二醯亞胺、N-溴丁二醯亞胺、氯、溴、碘)存在下,且使用催化量之自由基引發劑(諸如2,2'-偶氮二(2-甲基丙腈)(AIBN))進行方法P4。
方法P3較佳使用一或多種稀釋劑進行。適用於進行方法P3之溶劑較佳為基團鹵化條件下之惰性溶劑(例如四氯化碳)。尤其較佳為四氯化碳。
進行方法P4時,反應溫度可在相對廣泛範圍內變化。在鹵素-金
屬交換反應的情況中,所採用之溫度一般為-120℃至200℃,較佳溫度為-80℃至150℃。
為了進行方法P4,每莫耳式(VII)化合物一般使用1至2莫耳,較佳1莫耳鹵化劑。
本發明亦係關於用於製備式VI及VII化合物之方法(方法P5)。
其中U4定義為甲基、氯、溴或碘,及Z4、n、m、p、X及Y。
藉由與經取代或未經取代且在各末端碳上攜帶適當離去基(例如氯、溴、碘、甲磺酸酯基、甲苯磺酸酯基或三氟甲磺酸酯基)之烷基鏈(例如1,2-二溴乙烷)在適合鹼,例如無機碳酸鹽,諸如碳酸鉀、碳酸鈉或碳酸銫;金屬氫氧化物,諸如氫氧化鈉或氫氧化鉀;醇鹽,諸如第三丁醇鉀或第三丁醇鈉;金屬氫化物,諸如氫化鈉;醯胺,諸如二異丙胺基鋰存在下進行環化反應,自通式(VIII)之化合物(其中Z4為拉電子基團)(例如腈、羧酸酯)獲得通式(VI)或(VII)之化合物;參見例如Organic & Biomolecular Chemistry,(2012),10(31),6404-6409;WO2011/041694。方法P5亦可在諸如四正丁基銨溴化物或N,N'-二甲基-N,N'-三亞甲基脲(DMPU)之添加劑存在下進行。
為了進行方法P5,每莫耳式(VIII)化合物一般使用化學計量或過量之經取代或未經取代且各末端碳上攜帶適當離去基之烷基鏈。
所用溶劑可為所有在反應條件下呈惰性之慣用溶劑,或反應可在兩種或兩種以上此等溶劑之混合物中進行。
進行方法P5時,反應溫度可在相對廣泛範圍內變化。一般而言,採用之溫度為-10℃至150℃,較佳溫度為0℃至100℃。
本發明亦係關於用於製備式VI及VII化合物之方法(方法P6)。
其中U4定義為甲基、氯、溴或碘,U5定義為氫或Y,p為1,且Z4、n、m、X及Y如本文所定義。
藉由環丙烷化自通式(IX)之化合物獲得通式(VI)或(VII)之化合物;參見例如西蒙斯-史密斯反應(Simmons-Smith reaction):WO2012/165648;使用游離碳烯之環丙烷化:Chemical Reviews,(2003),103(4):1099-1132;使用金屬碳化物(metal carbinoid)之環丙烷化:Chemical Reviews,(1987),87(2):411-432。烯烴(IX)市場有售或可藉由文獻中所述之方法自市售前驅物製備(例如藉由維蒂希(Wittig)或霍納-沃茲沃思-埃蒙斯烯化(Horner-Wadsworth-Emmons olefination):Chemical Reviews,(1989),89,863-927及朱麗亞烯化(Julia olefination):Tetrahedron Letters,(1973),14,4833-4836;彼得森烯化(Peterson olefination):Journal of Organic Chemistry,(1968),33,780自酮製備;或如WO1991/11445中藉由烯醇化物或烯醇捕捉親電子試劑)。
所用溶劑可為所有在反應條件下呈惰性之慣用溶劑,或反應可在兩種或兩種以上此等溶劑之混合物中進行。
進行方法P6時,反應溫度可在相對廣泛範圍內變化。一般而言,採用之溫度為-120℃至150℃,溫度較佳為80℃至100℃。
應瞭解,在任何適當合成階段,取代基Z4可使用一或多個步驟,藉由熟習化學合成技術者通常所用之合成方法,自一個取代基定義轉化為另一個如上文指定之取代基定義,例如自腈藉由水解轉化為相應羧酸或藉由還原轉化為醛;自羧酸藉由還原轉化為羥基烷基或藉由去羧鹵化轉化為鹵素;自醛藉由維蒂希烯化或賽菲斯-吉爾伯特同系化(Seyferth-Gilbert homologation)轉化為相應烯烴或炔烴。
此外,亦應瞭解上文所述用於製備式(I)化合物之一些試劑及反應條件可能與中間化合物中存在之特定官能基不相容。在此等情況下,引入保護/脫除保護基工序或官能基相互轉化成合成有助於獲得所要產物。保護基之使用及選擇對於熟習化學合成技術者顯而易見(參見例如「Protective Groups in Organic Synthesis」;第三版;494-653及其中所引用之文獻)。熟習此項技術者將瞭解,在一些情況下,在如個別流程中所示引入既定試劑後,可能必須進行未個別地描述之額外途徑合成步驟以完成式(I)化合物之合成。熟習此項技術者將同樣瞭解可能必須以具體現實之暗示順序之外的順序進行上述流程中所說明之步驟的組合,以製備式(I)化合物。
根據本發明之方法P1及P6通常在大氣壓下進行。亦有可能在高壓或減壓下操作。
一般而言,反應混合物係在減壓下濃縮。剩餘之殘餘物可藉由諸如層析法或結晶之已知方法自仍可存在之任何雜質中釋放。
藉由慣用方法進行處理。一般而言,用水處理反應混合物,且分離出有機相且在乾燥後減壓濃縮。若適宜,則剩餘的殘餘物可藉由諸如層析、結晶或蒸餾之慣用方法自仍可存在之任何雜質釋放。
本發明化合物可根據上文所描述之通用製備方法來製備。然而
應理解,基於一般知識及可得到之公開案,熟習此項技術者將能夠根據需要合成之化合物中之每一者的特殊性來改適此方法。
因此,本發明提供式(II)化合物以及其可接受之鹽:
其中Z1、Z2、Z3、Z4、n、m、p、X及Y如本文所定義。
較佳本發明之式(II)化合物為:
-N-[2-(1-甲基環丙基)苯甲基]環丙胺
-N-[3-氟-2-(1-甲基環丙基)苯甲基]環丙胺
-N-{[4-(1-甲基環丙基)-1,3-苯并間二氧雜環戊烯-5-基]甲基}環丙胺
-N-[4-氯-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[4-甲基-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[4,5-二甲基-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[4,5-二氯-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[4,5-二甲氧基-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[5-溴-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[5-氯-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[5-氟-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[5-甲基-2-(1-甲基環丙基)苯甲基]環丙胺
-1-甲基-N-[5-甲基-2-(1-甲基環丙基)苯甲基]環丙胺
-1-{[5-甲基-2-(1-甲基環丙基)苯甲基]胺基}環丙烷甲腈
-N-[3-氯-2-(1-甲基環丙基)苯甲基]環丙胺
-N-[5-氯-2-(1-乙炔基環丙基)苯甲基]環丙胺
-N-[2-(1-乙炔基環丙基)-5-甲基苯甲基]環丙胺
-N-(5-氯-2-{1-[(三甲基矽烷基)乙炔基]環丙基}苯甲基)環丙胺
-N-(5-甲基-2-{1-[(三甲基矽烷基)乙炔基]環丙基}苯甲基)環丙胺
-1-{4-氯-2-[(環丙基胺基)甲基]苯基}環丙烷甲腈
-1-{2-[(環丙基胺基)甲基]-4-甲基苯基}環丙烷甲腈
-N-{2-[1-(甲氧基甲基)環丙基]-5-甲基苯甲基}環丙胺
-N-[2-(1-乙基環丙基)苯甲基]環丙胺
-N-[2-(1-乙基環丙基)-4-(三氟甲基)苯甲基]環丙胺
-N-[4-氯-2-(1-乙基環丙基)苯甲基]環丙胺
-N-[2-(1-乙基環丙基)-4-甲基苯甲基]環丙胺
-N-[2-(1-乙基環丙基)-5-氟-4-甲基苯甲基]環丙胺
-N-[2-(1-乙基環丙基)-5-(三氟甲基)苯甲基]環丙胺
-N-[5-氯-2-(1-乙基環丙基)苯甲基]環丙胺
-N-[2-(1-乙基環丙基)-5-甲基苯甲基]環丙胺
-N-[2-(1-乙基環丙基)-6-氟苯甲基]環丙胺
-N-[4-氯-2-(1-丙基環丙基)苯甲基]環丙胺
-N-[5-甲基-2-(1-丙基環丙基)苯甲基]環丙胺
-N-[2-(1-氯環丙基)-5-甲基苯甲基]環丙胺
-N-{2-[1,1'-聯(環丙基)-1-基]-5-甲基苯甲基}環丙胺
-N-{2-[1-(二氟甲基)環丙基]苯甲基}環丙胺
-N-{5-溴-2-[1-(二氟甲基)環丙基]苯甲基}環丙胺
-N-{5-氯-2-[1-(二氟甲基)環丙基]苯甲基}環丙胺
-N-{2-[1-(二氟甲基)環丙基]-5-氟苯甲基}環丙胺
-N-{2-[1-(二氟甲基)環丙基]-5-甲基苯甲基}環丙胺
-N-{2-溴-6-[1-(二氟甲基)環丙基]苯甲基}環丙胺
-N-[4-氯-2-(1-異丁基環丙基)苯甲基]環丙胺
-N-[2-(1-異丁基環丙基)-5-甲基苯甲基]環丙胺
-N-{5-氯-2-[1-(三氟甲基)環丙基]苯甲基}環丙胺
-N-{2-[1-(三氟甲基)環丙基]苯甲基}環丙胺
-N-{5-氟-2-[1-(三氟甲基)環丙基]苯甲基}環丙胺,以及其可接受之鹽。
本發明之其他令人感興趣的式(II)化合物為:
-N-[2-(1-甲氧基環丙基)苯甲基]環丙胺
-N-[5-氯-2-(1-甲氧基環丙基)苯甲基]環丙胺
-N-[2-(1-甲氧基環丙基)-5-甲基苯甲基]環丙胺
-N-[2-氟-3-甲基-6-(1-甲基環丙基)苯甲基]環丙胺
-N-(2',3'-二氫螺[環丙烷-1,1'-茚]-7'-基甲基)環丙胺
-N-[(2,2-二氯-3',4'-二氫-2'H-螺[環丙烷-1,1'-萘]-8'-基)甲基]環丙胺
-N-(3',4'-二氫-2'H-螺[環丙烷-1,1'-萘]-8'-基甲基)環丙胺
-N-[(2,2-二氯-2',3'-二氫螺[環丙烷-1,1'-茚]-7'-基)甲基]環丙胺
-N-[(6'-甲基-3',4'-二氫-2'H-螺[環丙烷-1,1'-萘]-8'-基)甲基]環丙胺,以及其可接受之鹽。
本發明因此亦提供式(IV)化合物:
其中Z4、n、m、p、X及Y如本文所定義,其限制條件為化合物(IV)不表示:
-2-(1-甲氧基環庚基)-5-(三氟甲基)苯甲醛
-(1S,2S)-2-乙氧基-2-(2-甲醯基苯基)環丙烷甲酸甲酯,或
-(1S,2R)-2-乙氧基-2-(2-甲醯基苯基)環丙烷甲酸甲酯。
本發明之較佳式(IV)化合物為:
-2-(1-甲基環丙基)苯甲醛
-4-氯-2-(1-甲基環丙基)苯甲醛
-4-氟-2-(1-甲基環丙基)苯甲醛
-4-甲基-2-(1-甲基環丙基)苯甲醛
-4-甲氧基-2-(1-甲基環丙基)苯甲醛
-4,5-二氟-2-(1-甲基環丙基)苯甲醛
-4,5-二甲基-2-(1-甲基環丙基)苯甲醛
-4,5-二甲氧基-2-(1-甲基環丙基)苯甲醛
-4-甲基-2,5-雙(1-甲基環丙基)苯甲醛
-5-氯-2-(1-甲基環丙基)苯甲醛
-5-氟-2-(1-甲基環丙基)苯甲醛
-5-甲基-2-(1-甲基環丙基)苯甲醛
-2,5-雙(1-甲基環丙基)苯甲醛
-3-氟-2-(1-甲基環丙基)苯甲醛
-1-(4-氯-2-甲醯基苯基)環丙烷甲腈
-1-(2-甲醯基-4-甲基苯基)環丙烷甲腈
-2-(1-乙基環丙基)-4-(三氟甲基)苯甲醛
-2-(1-乙基環丙基)-5-甲基苯甲醛
-4-氯-2-(1-丙基環丙基)苯甲醛
-5-氯-2-[1-(二氟甲基)環丙基]苯甲醛
-2-[1-(二氟甲基)環丙基]-5-甲基苯甲醛
-4-氯-2-(1-異丁基環丙基)苯甲醛
-2-(1-異丁基環丙基)-5-甲基苯甲醛
-1-(4-氯-2-甲醯基苯基)環丙烷甲酸,及
-1-(4-氯-2-甲醯基苯基)環丙烷甲酸甲酯。
本發明之其他令人感興趣的式(IV)化合物為:
-2-(1-乙基環丙基)-4-甲基苯甲醛
-2-(1-乙基環丙基)-6-氟苯甲醛
-4-氯-2-(1-乙基環丙基)苯甲醛
-5-甲基-2-(1-丙基環丙基)苯甲醛
-2-(1-乙基環丙基)-5-(三氟甲基)苯甲醛
-2-(1-乙基環丙基)-5-氟-4-甲基苯甲醛
-5-氯-2-(1-乙基環丙基)苯甲醛
-2-[1,1'-聯(環丙基)-1-基]-5-甲基苯甲醛
-5-溴-2-(1-甲基環丙基)苯甲醛,及
-5-溴-4-甲基-2-(1-甲基環丙基)苯甲醛。
本發明因此亦提供式(V)化合物:
其中U2為鹵素且Z4、n、m、p、X及Y如本文所定義,其限制條件為化合物(V)不表示:
-1-[2-(溴甲基)-3-氯苯基]環丁醇
-1-[2-(溴甲基)苯基]環丙烷甲腈
-1-[2-(溴甲基)-4-(三氟甲基)苯基]環庚基甲基醚
-2-(溴甲基)-1-(1-甲氧基環戊基)-4-(三氟甲基)苯
-2-(溴甲基)-1-(1-甲氧基環己基)-4-(三氟甲基)苯,或
-1-[2-(溴甲基)苯基]環戊烷甲腈。
以下式(V)化合物,其中U2為鹵素且Z4、n、m、p、X及Y如本文所定義,在化學資料庫及/或供應商資料庫中亦有提及,但無任何關於其製備及分離之參考文獻或資訊:
-1-[2-(氯甲基)-4,5-二甲氧基苯基]環戊烷甲腈。
本發明之較佳式(V)化合物為:
-1-(溴甲基)-3-氯-2-(1-甲基環丙基)苯。
本發明之其他令人感興趣的式(V)化合物為:
-1-(溴甲基)-2-[1-(三氟甲基)環丙基]苯
-2-(溴甲基)-4-氯-1-[1-(三氟甲基)環丙基]苯
-2-(溴甲基)-4-氟-1-[1-(三氟甲基)環丙基]苯
-1-(溴甲基)-2-[1-(二氟甲基)環丙基]-4-氟苯
-2-(溴甲基)-1-[1-(二氟甲基)環丙基]-4-氟苯
-1-(溴甲基)-2-[1-(二氟甲基)環丙基]苯
-2-(溴甲基)-4-氯-1-[1-(二氟甲基)環丙基]苯
-1-溴-2-(溴甲基)-3-[1-(二氟甲基)環丙基]苯,及
-4-溴-2-(溴甲基)-1-[1-(二氟甲基)環丙基]苯。
在另一態樣中,本發明亦係關於一種包含有效及無植物毒性量之式(I)活性化合物之殺真菌劑組合物。
表述「有效且無植物毒性之量」意謂足以控制或破壞在作物上存在或可能出現之真菌且不引起該等作物之任何明顯的植物毒性症狀的本發明組合物之量。視待控制之真菌、作物類型、氣候條件及本發明之殺真菌劑組合物中所包括之化合物而定,此類量可在廣泛圍內變
化。此量可藉由熟習此項技術者能力範圍內之系統田間試驗來確定。
因此,根據本發明,提供一種殺真菌劑組合物,其包含有效量之如本文所定義之式(I)化合物作為活性成分及農業上可接受之載體、載劑或填充劑。
根據本發明,術語「載體」表示與式(I)之活性化合物組合或締合以使其更容易施用、尤其施用於植物部分之天然或合成有機或無機化合物。因此,此載體一般為惰性的且應為農業上可接受的。該載體可為固體或液體。適合載體之實例包括黏土、天然或合成矽酸鹽、二氧化矽、樹脂、蠟、固體肥料、水、醇(詳言之丁醇)、有機溶劑、無機及植物油及其衍生物。亦可使用此類載體之混合物。
本發明之組合物亦可包含額外組分。特定言之,組合物可進一步包含界面活性劑。界面活性劑可為離子型或非離子型乳化劑、分散劑或濕潤劑,或此類界面活性劑之混合物。可提及例如聚丙烯酸鹽、木質磺酸鹽、酚磺酸或萘磺酸鹽、環氧乙烷與脂肪醇或與脂肪酸或與脂肪胺之聚縮合物、經取代之酚(詳言之烷基酚或芳基酚)、磺化丁二酸酯之鹽、牛磺酸衍生物(詳言之牛磺酸烷基酯)、聚氧乙基化醇或酚之磷酸酯、多元醇之脂肪酸酯及含有硫酸酯基、磺酸酯基及磷酸酯基官能基之上述化合物之衍生物。當活性化合物及/或惰性載體不溶於水時且當施用之載劑(vector agent)為水時,一般必需存在至少一種界面活性劑。較佳地,界面活性劑含量按組合物之重量計可占5%至40%。
視情況而言,亦可包括額外組分,例如保護性膠體、黏著劑、增稠劑、搖變劑、滲透劑、穩定劑、螯合劑。更一般而言,活性化合物可與符合常用調配技術之任何固體或液體添加劑組合。
一般而言,本發明組合物可含有0.05至99重量%活性化合物,較佳10重量%至70重量%。
本發明之組合物可以下列各種形式及調配物使用:諸如氣霧劑施配器、膠囊懸浮液、冷霧濃縮物、可撒佈散劑、可乳化濃縮物、水包油乳液、油包水乳液、囊封顆粒、精細顆粒、用於種子處理之可流動濃縮物、氣體(在壓力下)、產氣產品、顆粒、熱霧濃縮物、大顆粒、微顆粒、油分散性粉末、可與油混溶之可流動濃縮物、可與油混溶之液體、糊劑、植物桿型劑、用於乾式種子處理之粉末、塗有殺蟲劑之種子、可溶性濃縮物、可溶性粉末、用於種子處理之溶液、懸浮液濃縮物(可流動濃縮物)、超低容量(ULV)液體、超低容量(ULV)懸浮液、水分散性顆粒或錠劑、用於漿料處理之水分散性粉末、水溶性顆粒或錠劑、用於種子處理之水溶性粉末及可濕性粉末。此等組合物不僅包括準備藉助於適合裝置(諸如噴霧或撒粉裝置)施用於待處理之植物或種子的組合物,而且包括在施用於作物之前必須經稀釋之濃縮市售組合物。
調配物可以本身已知的方式製備,例如藉由將活性成分與至少一種以下慣用物質混合:增量劑、溶劑或稀釋劑、佐劑、乳化劑、分散劑及/或黏合劑或固定劑、濕潤劑、拒水劑,適宜時乾燥劑及UV穩定劑,及適宜時染料及顏料、消泡劑、防腐劑、無機及有機增稠劑、黏著劑、赤黴素以及其他加工助劑,及亦水。視待製備之調配物類型而定,需要其他處理步驟,例如濕式研磨、乾式研磨及造粒。
本發明活性成分可按原樣存在或呈其(市售)調配物形式及呈自與其他(已知)活性成分之混合物形式的此等調配物製備之使用形式,該等活性成分諸如殺蟲劑、引誘劑、滅菌劑、殺細菌劑、殺蟎劑、殺線蟲劑、殺真菌劑、生長調節劑、除草劑、肥料、安全劑、生物製劑及/或化學訊息傳遞素。
本發明之式(I)化合物及殺真菌劑組合物可用於治癒性或預防性控制植物或作物之植物病原性真菌,詳言之銹病。
因此,根據本發明之另一態樣,提供一種用於治癒性或預防性控制植物或作物之植物病原性真菌(詳言之銹病)的方法,其特徵在於本發明之式(I)化合物或殺真菌劑組合物施用於種子、植物或植物之果實或正在生長植物或需要生長植物之土壤。
本發明之處理方法亦可適用於處理繁殖材料,諸如塊莖或根莖,亦及種子、幼苗或移植之幼苗及植物或移植之植物。此處理方法亦可適用於處理根。本發明之處理方法亦可適用於植物之地上部分,諸如相關植物之幹、莖或梗、葉、花朵及果實。
根據本發明,可處理所有植物及植物部分。植物意謂所有植物及植物群體,諸如所要及非所要的野生植物、栽培品種及植物品種(無論是否可受植物品種或植物育種家之權利保護)。栽培品種及植物品種可為藉由習知繁殖及育種方法獲得之植物,該等方法可藉由一或多種生物技術方法輔助或補充,諸如藉由使用雙單倍體、原生質體融合、無規及定向突變誘發、分子或遺傳標記或藉由生物工程改造及基因工程改造方法。植物部分意謂植物之所有地上及地下部分及器官,諸如芽、葉、花及根,藉此列舉例如葉、針葉、莖、分枝、花、子實體、果實及種子以及根、球莖及根莖。作物及無性及有性繁殖材料(例如插條、球莖、根莖、長匐莖及種子)亦屬於植物部分。
在可受本發明之方法保護之植物中,可提及主要田間作物,如玉米、大豆、棉花、甘藍型油籽(諸如甘藍型油菜(Brassica napus)(例如芥花)、蕪菁(Brassica rapa)、芥菜(B.juncea)(例如芥子)及埃塞俄比亞芥菜(Brassica carinata))、水稻、小麥、甜菜、甘蔗、燕麥、黑麥、大麥、粟、黑小麥、亞麻、蔓藤以及各種植物學分類群之各種水果及蔬菜,諸如薔薇科(Rosaceae sp.)(例如仁果類水果,諸如蘋果及梨;及亦核果類水果,諸如杏、櫻桃、杏仁及桃;漿果類水果,諸如草莓)、茶鹿子科(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、樺科
(Betulaceae sp.)、漆樹科(Anacardiaceae sp.)、山毛櫸科(Fagaceae sp.)、桑科(Moraceae sp.)、木樨科(Oleaceae sp.)、獼猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉樹及種植林)、茜草科(Rubiaceae sp.)(例如咖啡)、茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、蕓香科(Rutaceae sp.)(例如檸檬、柑橘及葡萄柚);茄科(Solanaceae sp.)(例如蕃茄、馬鈴薯、胡椒、茄子)、百合科(Liliaceae sp.)、菊科(Compositiae sp.)(例如萵苣、朝鮮薊及菊苣,包括根菊苣、苦苣或常見菊苣)、傘形科(Umbelliferae sp.)(例如胡蘿蔔、香芹、旱芹及根芹菜)、葫蘆科(Cucurbitaceae sp.)(例如黃瓜(包括醃漬黃瓜)、南瓜、西瓜、葫蘆及甜瓜)、蔥科(Alliaceae sp.)(例如洋蔥及韭菜)、十字花科(Cruciferae sp.)(例如白球甘藍、紅球甘藍、椰菜、花椰菜、抱子甘藍、白菜、球莖甘藍、蘿蔔、辣根、水芹、大白菜)、豆科(Leguminosae sp.)(例如花生、豌豆及豆子,豆子諸如蔓菜豆及蠶豆)、藜科(Chenopodiaceae sp.)(例如飼料甜菜、葉甜菜、菠菜、甜菜根)、錦葵科(Malvaceae)(例如秋葵)、天門冬科(Asparagaceae)(例如蘆筍);園藝及森林作物;觀賞植物;以及此等作物之經基因修飾之同系物。
本發明之處理方法可用於處理經基因修飾之生物(GMO),例如植物或種子。經基因改造之植物(或轉殖基因植物)為異源基因已穩定整合入基因組中之植物。表述「異源基因」基本上意謂在植物外部提供或組裝且當引入細胞核、葉綠體或粒線體基因組中時藉由表現相關蛋白質或多肽或藉由(使用例如反義技術、共抑制技術或RNA干擾-RNAi技術)下調或靜默植物中所存在之其他基因而賦予經轉化植物新穎或改良之農藝學特性或其他特性的基因。位於基因組中之異源基因亦稱為轉殖基因。由在植物基因組中之特定位置定義之轉殖基因稱為轉化或轉殖基因品項。
視植物物種或植物栽培品種、其位置及生長條件(土壤、氣候、生長期、食料)而定,根據本發明之處理亦可產生超加性(「協同」)效應。因此,舉例而言,有可能實現施用率降低及/或活性範圍變寬及/或可根據本發明使用之活性化合物及組合物之活性增加、植物生長較好、對高溫或低溫之耐受性增加、對乾旱或水或土壤鹽含量之耐受性增加、開花效能增加、容易收穫、成熟加速、收穫產量較高、果實較大、植物高度較高、葉片顏色較綠、開花較早、收穫產物之品質較高及/或營養價值較高、果實內之糖濃度較高、收穫產物之儲存穩定性及/或可加工性較好,該等效果超過實際預期效果。
在特定施用量下,本發明之活性化合物組合亦可在植物中具有增強效果。因此,其亦適用於動員植物之防禦系統抵抗不必要之微生物侵襲。適當時,此可為本發明之組合例如抵抗真菌之活性增強的原因之一。在本發明之背景下,植物增強(抗性誘導)物質應理解為意謂能夠以如下方式刺激植物之防禦系統的彼等物質或物質之組合:當隨後接種不必要之微生物時,經處理之植物顯示對此等微生物實質程度的抗性。在本發明情況下,非所要微生物應理解為意謂植物病原性真菌、細菌及病毒。因此,本發明之物質可用於保護植物在處理後某一時間段內免受上述病原體侵襲。實現保護之時間段一般在用活性化合物處理植物之後1天至10天,較佳1天至7天。
較佳根據本發明處理之植物及植物栽培品種包括具有賦予此等植物尤其有利、適用之性狀之遺傳物質的所有植物(不論藉由育種及/或生物技術方式獲得)。
亦較佳根據本發明處理之植物及植物栽培品種對一或多種生物壓力具有抗性,亦即該等植物顯示對動物及微生物害蟲(諸如對線蟲、昆蟲、蟎蟲、植物病原性真菌、細菌、病毒及/或類病毒)之較好防禦。
抗線蟲植物之實例描述於例如美國專利申請案第11/765,491號、第11/765,494號、第10/926,819號、第10/782,020號、第12/032,479號、第10/783,417號、第10/782,096號、第11/657,964號、第12/192,904號、第11/396,808號、第12/166,253號、第12/166,239號、第12/166,124號、第12/166,209號、第11/762,886號、第12/364,335號、第11/763,947號、第12/252,453號、第12/209,354號、第12/491,396號或第12/497,221號中。
亦可根據本發明處理之植物及植物栽培品種為對一或多種非生物性壓力具有抗性之彼等植物。非生物性壓力條件可包括例如乾旱、低溫暴露、熱暴露、滲透壓力、洪水、增加之土壤鹽度、增加之礦物質暴露、臭氧暴露、高曝光、氮養分之有限可用性、磷養分之有限可用性、避蔭。
亦可根據本發明處理之植物及植物栽培品種為特徵在於產量特徵增強之彼等植物。該等植物之產量增加可為例如改良植物生理學、生長及發育(諸如水利用效率、水保持效率、改良之氮使用、增強之碳同化、改良之光合成、增加之發芽效率及加速成熟)之結果。產量可另外受改良之植物株型影響(在壓力及非壓力條件下),該改良之植物株型包括(但不限於)早期開花、對雜交種子生產之開花控制、幼苗活力、植物大小、節間數目及距離、根生長、種子大小、果實大小、豆莢大小、豆莢或穗數目、每個豆莢或穗之種子數目、種子質量、增強之種子填充、降低之種子散佈度、降低之豆莢開裂性及抗倒伏性。其他產量特點包括種子組成,諸如碳水化合物含量、蛋白質含量、油含量及組成、營養價值、抗營養化合物減少、改良之可加工性及較好儲存穩定性。
具有上述特點之植物的實例係以非限制性方式列舉於表A中。
可根據本發明處理之植物為已表現雜種優勢或雜交活力之特徵
的雜交植物,該特徵一般產生較高產量、活力、健康及對生物及非生物壓力之抗性)。此類植物通常由將近親配種之雄性不育親本系(母本)與另一近親配種之雄性可育親本系(父本)雜交來產生。雜交種子通常自雄性不育植物收穫且出售給種植者。雄性不育植物有時(例如在玉米中)可由去雄花穗(亦即機械移除雄性生殖器官(或雄性花朵))產生,但雄性不育更通常為植物基因組中遺傳決定因素的結果。在彼情況下,且尤其當種子為自雜交植物收穫之所需產物時,通常適用於確保雜交植物之雄性可育性完全恢復。此可藉由確保雄性親本具有適當可育性恢復基因來實現,該等基因能夠使含有造成雄性不育之遺傳決定因素之雜交植物恢復雄性可育性。雄性不育之遺傳決定因素可位於細胞質中。細胞質雄性不育(CMS)之實例例如描述於蕓薹屬物種(WO 92/05251、WO 95/09910、WO 98/27806、WO 05/002324、WO 06/021972及US 6,229,072)中。然而,雄性不育之遺傳決定因素亦可位於細胞核基因組中。雄性不育植物亦可藉由植物生物技術方法(諸如基因工程改造)獲得。獲得雄性不育植物之尤其適用方式描述於WO 89/10396中,其中例如核糖核酸酶(諸如雄性不育基因(barnase))選擇性表現在雄蕊之絨氈層細胞中。隨後可藉由在絨氈層細胞中表現核糖核酸酶抑制劑(諸如芽胞桿菌RNA酶抑制劑)恢復可育性(例如WO 91/02069)。
可根據本發明處理之植物或植物栽培品種(藉由植物生物技術方法(諸如基因工程改造)獲得)為耐除草劑植物,亦即對一或多種既定除草劑具有耐受性之植物。此類植物可藉由基因轉化或藉由選擇含有賦予此類除草劑耐受性之突變之植物獲得。
耐除草劑植物為例如耐草甘膦植物,亦即對除草劑草甘膦或其鹽具耐受性之植物。可藉由不同方式使植物對草甘膦具有耐受性。舉例而言,耐草甘膦植物可藉由用編碼酶5-烯醇丙酮醯莽草酸-3-磷酸合
成酶(EPSPS)之基因轉化植物來獲得。此類EPSPS基因之實例為細菌鼠傷寒沙門桿菌(Salmonella typhimurium)之AroA基因(突變CT7)(Comai等人,1983,Science 221,370-371),細菌土壤桿菌種(Agrobacterium sp.)之CP4基因(Barry等人,1992,Curr.Topics Plant Physiol.7,139-145),編碼矮牽牛(Petunia)EPSPS(Shah等人,1986,Science 233,478-481)、番茄EPSPS(Gasser等人,1988,J.Biol.Chem.263,4280-4289)或龍爪稷(Eleusine)EPSPS(WO 01/66704)之基因。其亦可為如在例如EP 0837944、WO 00/66746、WO 00/66747或WO02/26995中所描述之突變EPSPS。耐草甘膦植物亦可藉由如美國專利第5,776,760及第5,463,175號中所描述表現編碼草甘膦氧化還原酶之基因而獲得。耐草甘膦植物亦可藉由如例如WO 02/36782、WO 03/092360、WO 05/012515及WO 07/024782中所描述表現編碼草甘膦乙醯基轉移酶之基因來獲得。耐草甘膦植物亦可藉由選擇含有上述基因之天然存在之突變的植物而獲得,如例如WO 01/024615或WO 03/013226中所述。表現賦予草甘膦耐受性之EPSPS基因之植物描述於例如美國專利申請案第11/517,991號、第10/739,610號、第12/139,408號、第12/352,532號、第11/312,866號、第11/315,678號、第12/421,292號、第11/400,598號、第11/651,752號、第11/681,285號、第11/605,824號、第12/468,205號、第11/760,570號、第11/762,526號、第11/769,327號、第11/769,255號、第11/943801號或第12/362,774號中。包含賦予草甘膦耐受性之其他基因(諸如去羧酶基因)的植物在例如美國專利申請案11/588,811、11/185,342、12/364,724、11/185,560或12/423,926中描述。
其他耐除草劑植物為例如對抑制酶麩醯胺酸合成酶之除草劑(諸如畢拉草(bialaphos)、草胺膦(phosphinothricin)或固殺草(glufosinate))具有耐受性之植物。此類植物可藉由表現使除草劑去除毒性之酶或對
抑制具抗性之突變麩醯胺酸合成酶獲得,例如美國專利申請案第11/760,602號中所描述。一種此類有效去除毒性之酶為編碼草胺膦乙醯轉移酶之酶(諸如來自鏈黴菌(Streptomyces)種之bar或pat蛋白)。表現外源性草胺膦乙醯轉移酶之植物例如描述於美國專利第5,561,236號;第5,648,477號;第5,646,024號;第5,273,894號;第5,637,489號;第5,276,268號;第5,739,082號;第5,908,810號及第7,112,665號中。
其他耐除草劑植物亦為對抑制羥苯基丙酮酸雙加氧酶(HPPD)之除草劑具有耐受性之植物。羥苯基丙酮酸雙加氧酶為催化將對羥苯基丙酮酸(HPP)轉化成尿黑酸之反應的酶。對HPPD抑制劑具耐受性之植物可用編碼天然存在之抗HPPD酶之基因或編碼突變或嵌合HPPD酶之基因轉化,如在WO 96/38567、WO 99/24585、WO 99/24586、WO 2009/144079、WO 2002/046387或US 6,768,044中所描述。儘管HPPD抑制劑抑制天然HPPD酶,但對HPPD抑制劑之耐受性亦可藉由用編碼某些使得能夠形成尿黑酸之基因轉化植物來獲得。此類植物及基因描述於WO 99/34008及WO 02/36787中。植物對HPPD抑制劑之耐受性亦可藉由用編碼具有預苯酸去氫酶(PDH)活性之酶的基因外加編碼耐HPPD酶之基因使植物轉化來改良,如WO 2004/024928中所述。另外,可藉由將編碼能夠代謝或降解HPPD抑制劑之酶(諸如WO 2007/103567及WO 2008/150473中所示之CYP450酶)的基因添加至植物基因組中來使植物對HPPD抑制劑除草劑更具有耐受性。
其他耐除草劑植物為對乙醯乳酸合成酶(ALS)抑制劑具有耐受性之植物。已知ALS抑制劑包括例如磺醯脲、咪唑啉酮、三唑并嘧啶、嘧啶基氧基(硫代)苯甲酸鹽及/或磺醯胺基羰基三唑啉酮除草劑。已知ALS酶(亦稱為乙醯羥基酸合成酶,AHAS)之不同突變賦予不同除草劑及除草劑組耐受性,如例如Tranel及Wright(2002,Weed Science
50:700-712)中以及美國專利第5,605,011號、第5,378,824號、第5,141,870號及第5,013,659號中所描述。耐磺醯脲植物及耐咪唑啉酮植物在美國專利第5,605,011號;第5,013,659號;第5,141,870號;第5,767,361號;第5,731,180號;第5,304,732號;第4,761,373號;第5,331,107號;第5,928,937號及第5,378,824號及國際公開案WO 96/33270中描述。其他咪唑啉酮耐受性植物亦描述於例如WO 2004/040012、WO 2004/106529、WO 2005/020673、WO 2005/093093、WO 2006/007373、WO 2006/015376、WO 2006/024351及WO 2006/060634中。其他耐磺醯脲植物及耐咪唑啉酮植物亦描述於例如WO 07/024782及美國專利申請案第61/288958號中。
對咪唑啉酮及/或磺醯脲具有耐受性之其他植物可藉由誘導突變誘發、在除草劑存在下於細胞培養物中進行選擇、或突變育種獲得,如例如關於大豆之美國專利5,084,082、關於水稻之WO 97/41218、關於甜菜之美國專利5,773,702及WO 99/057965、關於萵苣之美國專利5,198,599或關於向日葵之WO 01/065922中所描述。
亦可根據本發明處理之植物或植物栽培品種(藉由植物生物技術方法,諸如基因工程改造獲得)為耐昆蟲轉殖基因植物,亦即對某些目標昆蟲之侵襲具有抗性之植物。此類植物可藉由基因轉化或藉由選擇含有賦予此類耐昆蟲性之突變之植物獲得。
如本文所用,「耐昆蟲轉殖基因植物」包括含有至少一個轉殖基因之任何植物,該至少一個轉殖基因包含編碼以下之編碼序列:
1)來自蘇雲金芽孢桿菌(Bacillus thuringiensis)之殺昆蟲晶體蛋白或其殺昆蟲部分,諸如由Crickmore等人(1998,Microbiology and Molecular Biology Reviews,62:807-813)所列,由Crickmore等人(2005)在蘇雲金芽孢桿菌毒素命名法中,在http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)中在線更新
之殺昆蟲晶體蛋白或其殺昆蟲部分,例如Cry蛋白類之蛋白Cry1Ab、Cry1Ac、Cry1B、Cry1C、Cry1D、Cry1F、Cry2Ab、Cry3Aa、或Cry3Bb或其殺昆蟲部分(例如EP 1999141及WO 2007/107302),或由合成基因編碼之此類蛋白,如例如描述於美國專利申請案第12/249,016號中;或
2)來自蘇雲金芽孢桿菌之晶體蛋白或其部分,其在來自蘇雲金芽孢桿菌之第二其他晶體蛋白或其部分,諸如由Cry34及Cry35晶體蛋白組成之二元毒素(Moellenbeck等人2001,Nat.Biotechnol.19:668-72;Schnepf等人2006,Applied Environm.Microbiol.71,1765-1774)或由Cry1A或Cry1F蛋白及Cry2Aa或Cry2Ab或Cry2Ae蛋白組成之二元毒素(美國專利申請案第12/214,022號及EP 08010791.5)存在下具殺蟲性;或
3)包含來自蘇雲金芽孢桿菌之不同殺昆蟲晶體蛋白之部分的雜交殺昆蟲蛋白質,諸如上述1)之蛋白質之雜交體或上述2)之蛋白質之雜交體,例如由玉米品項MON89034產生之Cry1A.105蛋白質(WO 2007/027777);或
4)上述1)至3)中任一項之蛋白質,其中一些(特定言之1至10個)胺基酸已置換為另一胺基酸獲得對目標昆蟲物種之較高殺昆蟲活性及/或擴大受影響之目標昆蟲物種之範圍,及/或此係由於在選殖或轉化期間引入編碼DNA中之變化,諸如玉米品項MON863或MON88017中之Cry3Bb1蛋白質,或玉米品項MIR604中之Cry3A蛋白質;或
5)來自蘇雲金芽孢桿菌或仙人掌桿菌(Bacillus cereus)之殺蟲分泌蛋白或其殺蟲部分,諸如在http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html中所列之營養期殺昆蟲(VIP)蛋白,例如來自VIP3Aa蛋白類之蛋白質;或
6)來自蘇雲金芽孢桿菌或仙人掌桿菌之分泌蛋白,其在來自蘇
雲金芽孢桿菌或仙人掌桿菌之第二分泌蛋白存在下具有殺昆蟲性,諸如由VIP1A及VIP2A蛋白質構成之二元毒素(WO 94/21795);或
7)包含來自蘇雲金芽孢桿菌或仙人掌桿菌之不同分泌蛋白之部分的雜交殺昆蟲蛋白,諸如上述1)中之蛋白質之雜交體或上述2)中之蛋白質之雜交體;或
8)上述5)至7)中任一項之蛋白質,其中一些(特定言之1至10個)胺基酸已置換為另一胺基酸置獲得對目標昆蟲物種之較高殺昆蟲活性及/或擴大受影響之目標昆蟲物種之範圍,及/或此係由於在選殖或轉化期間引入編碼DNA中之變化(同時仍編碼殺昆蟲蛋白),諸如棉花品項COT102中之VIP3Aa蛋白;或
9)來自蘇雲金芽孢桿菌或仙人掌桿菌之分泌蛋白,其在來自蘇雲金芽孢桿菌之晶體蛋白存在下具殺昆蟲性,諸如由VIP3及Cry1A或Cry1F組成之二元毒素(美國專利申請案第61/126083號及第61/195019號),或由VIP3蛋白及Cry2Aa或Cry2Ab或Cry2Ae蛋白組成之二元毒素(美國專利申請案第12/214,022號及EP 08010791.5)。
10)上述9)之蛋白質,其中一些(特定言之1至10個)胺基酸已置換為另一胺基酸獲得對目標昆蟲物種之較高的殺昆蟲活性及/或擴大受影響之目標昆蟲物種的範圍,及/或此係由於在選殖或轉化期間引入編碼DNA中之變化(同時仍編碼殺昆蟲蛋白)
當然,如本文所用,耐昆蟲轉殖基因植物亦包括包含編碼上述類別1至10中任一項之蛋白質之基因組合的任何植物。在一個實施例中,耐昆蟲植物含有一種以上編碼上述類別1至10中任一項之蛋白質的轉殖基因,以當使用針對不同目標昆蟲物種之不同蛋白質時擴大受影響之目標昆蟲物種之範圍,或藉由使用對相同目標昆蟲物種具有殺昆蟲性但具有不同作用模式(諸如結合於昆蟲體內之不同受體結合位點)之不同蛋白質來延遲植物之抗昆蟲性發展。
如本文所用,「耐昆蟲轉殖基因植物」進一步包括含有至少一種轉殖基因之任何植物,該至少一種轉殖基因所包含之序列在表現時會產生雙股RNA,當被植物害蟲攝入時會抑制此害蟲之生長,如例如WO 2007/080126、WO 2006/129204、WO 2007/074405、WO 2007/080127及WO 2007/035650中所描述。
亦可根據本發明處理之植物或植物栽培品種(藉由植物生物技術方法,諸如基因工程改造獲得)對非生物壓力具有耐受性。此類植物可藉由基因轉化或藉由選擇含有賦予此類抗壓力性之突變之植物獲得。尤其適用之抗壓力植物包括:
1)含有能夠降低植物細胞或植物中之聚(ADP-核糖)聚合酶(PARP)基因之表現及/或活性之轉殖基因的植物,如WO 00/04173、WO/2006/045633、EP 04077984.5或EP 06009836.5中所描述。
2)包含能夠降低植物或植物細胞之PARG編碼基因之表現及/或活性的耐壓力增強轉殖基因的植物,如例如WO 2004/090140中所述。
3)含有編碼用於菸鹼醯胺腺嘌呤二核苷酸補救合成路徑之植物功能性酶(包括菸醯胺酶、菸鹼酸磷酸核糖轉移酶、菸鹼酸單核苷酸腺苷酸轉移酶、菸鹼醯胺腺嘌呤二核苷酸合成酶或菸鹼醯胺磷酸核糖轉移酶)之耐壓力增強轉殖基因之植物,如例如在EP 04077624.7、WO 2006/133827、PCT/EP07/002433、EP 1999263或WO 2007/107326中所描述。
亦可根據本發明處理之植物或植物栽培品種(藉由植物生物技術方法,諸如基因工程改造獲得)顯示收穫產物之數量、品質及/或儲存穩定性改變及/或收穫產物之特定成分之特性改變,諸如:
1)合成改質澱粉之轉殖基因植物,該改質澱粉與野生型植物細胞或植物中之合成澱粉相比,其物理化學特徵(尤其直鏈澱粉含量或
直鏈澱粉/支鏈澱粉比率、分枝程度、平均鏈長、側鏈分佈、黏度特性、膠凝強度、澱粉粒度及/或澱粉顆粒形態)改變,以使其更適於特定應用。合成改質澱粉之該等轉殖基因植物揭示於例如EP 0571427、WO 95/04826、EP 0719338、WO 96/15248、WO 96/19581、WO 96/27674、WO 97/11188、WO 97/26362、WO 97/32985、WO 97/42328、WO 97/44472、WO 97/45545、WO 98/27212、WO 98/40503、WO99/58688、WO 99/58690、WO 99/58654、WO 00/08184、WO 00/08185、WO 00/08175、WO 00/28052、WO 00/77229、WO 01/12782、WO 01/12826、WO 02/101059、WO 03/071860、WO 2004/056999、WO 2005/030942、WO 2005/030941、WO 2005/095632、WO 2005/095617、WO 2005/095619、WO 2005/095618、WO 2005/123927、WO 2006/018319、WO 2006/103107、WO 2006/108702、WO 2007/009823、WO 00/22140、WO 2006/063862、WO 2006/072603、WO 02/034923、EP 06090134.5、EP 06090228.5、EP 06090227.7、EP 07090007.1、EP 07090009.7、WO 01/14569、WO 02/79410、WO 03/33540、WO 2004/078983、WO 01/19975、WO 95/26407、WO 96/34968、WO 98/20145、WO 99/12950、WO 99/66050、WO 99/53072、US 6,734,341、WO 00/11192、WO 98/22604、WO 98/32326、WO 01/98509、WO 01/98509、WO 2005/002359、US 5,824,790、US 6,013,861、WO 94/04693、WO 94/09144、WO 94/11520、WO 95/35026、WO 97/20936
2)合成非澱粉碳水化合物聚合物或合成與無基因修飾之野生型植物相比特性改變之非澱粉碳水化合物聚合物的轉殖基因植物。實例為產生多聚果糖,尤其菊糖及聚左糖型多聚果糖之植物,如在EP 0663956、WO 96/01904、WO 96/21023、WO 98/39460及WO 99/24593
中所揭示,產生α-1,4-葡聚糖之植物,如在WO 95/31553、US 2002031826、US 6,284,479、US 5,712,107、WO 97/47806、WO 97/47807、WO 97/47808及WO 00/14249中所揭示,產生α-1,6支鏈α-1,4-葡聚糖之植物,如在WO 00/73422中所揭示,產生蓮子草素(alternan)之植物,如在例如WO 00/47727、WO 00/73422、EP 06077301.7、US 5,908,975及EP 0728213中所揭示,
3)產生透明質酸之轉殖基因植物,如例如WO 2006/032538、WO 2007/039314、WO 2007/039315、WO 2007/039316、JP 2006304779及WO 2005/012529中所揭示。
4)轉殖基因植物或雜交植物,諸如具有諸如『高可溶固體含量』、『低刺激性』(LP)及/或『長儲存期』(LS)之特徵的洋蔥,如美國專利申請案第12/020,360號及第61/054,026號中所述。
亦可根據本發明處理之植物或植物栽培品種(藉由植物生物技術方法,諸如基因工程改造獲得)為纖維特徵改變之植物,諸如棉花植物。此類植物可藉由基因轉化或藉由選擇含有賦予此類改變之纖維特徵之突變的植物獲得,且該等植物包括:
a)含有纖維素合成酶基因之改變形式的植物,諸如棉花植物,如在WO 98/00549中所描述
b)含有rsw2或rsw3同源核酸之改變形式之植物,諸如棉花植物,如WO 2004/053219中所述。
c)蔗糖磷酸合成酶之表現增加之植物,諸如棉花植物,如WO 01/17333中所述
d)蔗糖合成酶之表現增加之植物,諸如棉花植物,如WO 02/45485中所述
e)基於纖維細胞之胞間連絲閘控之時序例如藉由下調纖維選擇性β-1,3-葡聚糖酶而改變的植物,諸如棉花植物,如在WO
2005/017157中所描述或在如EP 08075514.3或美國專利申請案第61/128,938號中所描述
f)具有例如藉由N-乙醯葡萄糖胺轉移酶基因(包括nodC及幾丁質合成酶基因)之表現改變反應性之纖維的植物,諸如棉花植物,如在WO 2006/136351中所描述
亦可根據本發明處理之植物或植物栽培品種(藉由植物生物技術方法,諸如基因工程改造獲得)為油型態特徵改變之植物,諸如油菜或相關蕓苔屬植物。此類植物可藉由基因轉化或藉由選擇包含賦予此類改變之油分佈特徵的突變之植物而獲得,且該等植物包括:
a)產生具有高油酸含量之油之植物,諸如油菜植物,如例如US 5,969,169、US 5,840,946或US 6,323,392或US 6,063,947中所描述
b)產生具有低次亞麻油酸含量之油之植物,諸如油菜植物,如US 6,270,828、US 6,169,190或US 5,965,755中所描述
c)產生具有低含量飽和脂肪酸之油的植物,諸如油菜植物,如例如在美國專利第5,434,283號或美國專利申請案第12/668303號中所描述
亦可根據本發明處理之植物或植物栽培品種(可藉由植物生物技術方法,諸如基因工程改造獲得)為落粒特徵改變之植物,諸如油菜或相關蕓苔屬植物。此類植物可藉由基因轉化或藉由選擇含有賦予該等改變之落粒特徵之突變的植物獲得且包括落粒延遲或減少之植物,諸如油菜植物,如美國專利申請案第61/135,230號、WO 09/068313及WO 10/006732中所描述。
可根據本發明處理之特別適用的轉殖基因植物為含有轉化品項或轉化品項之組合的植物,在美利堅合眾國,其為美國農業部(United States Department of Agriculture;USDA)之動植物衛生檢驗署(Animal and Plant Health Inspection Service;APHIS)的非管制狀態之
申請主題,不論該等申請已授予或仍未決。在任何時候,此資訊均容易自APHIS(4700 River Road Riverdale,MD20737,USA)獲得,例如在其網際網路站點(URL http://www.aphis.usda.gov/brs/not_reg.html)上。在本申請案申請當天,與APHIS申請中或由APHIS授予之非管制狀態的申請為表B中所列彼等申請,其含有以下資訊:
-申請:申請之識別編號。轉化品項之技術描述可參考此申請編號見於個別申請文件中,該等申請文件可自APHIS獲得,例如在APHIS網站上。此等描述以引用的方式併入本文中。
-申請之擴展:參考要求擴展之前一申請。
-機構:提交申請之實體之名稱。
-管制物品:相關植物物種。
-轉殖基因表現型:由轉化品項賦予植物之特點。
-轉化品項或系:要求非管制狀態之品項(有時亦稱為系)之名稱。
-APHIS文件:與申請有關之由APHIS公開之各種文件,且其可受APHIS要求。
含有單個轉化品項或轉化品項之組合的額外尤其適用的植物列於例如多個國家的或地區的管制機構之資料庫(參見例如http://gmoinfo.jrc.it/gmp_browse.aspx及http://www.agbios.com/dbase.php)中。可根據本發明處理的尤其適用之轉殖基因植物為含有轉化品項或轉化品項組合之植物,且其列於例如多個國家或地方之管理機構的資料庫中,包括品項1143-14A(棉花,昆蟲控制,未寄存,描述於WO 2006/128569中);品項1143-51B(棉花,昆蟲控制,未寄存,描述於中WO 2006/128570中);品項1445(棉,耐除草劑,未寄存,描述於US-A 2002-120964或WO 02/034946中);品項17053(水稻,耐除草劑,寄存為PTA-9843,描述於WO 2010/117737中);品項17314(水
稻,耐除草劑,寄存為PTA-9844,描述於WO 2010/117735中);品項281-24-236(棉花,昆蟲控制-耐除草劑,寄存為PTA-6233,描述於WO 2005/103266或US-A 2005-216969中);品項3006-210-23(棉花,昆蟲控制-耐除草劑,寄存為PTA-6233,描述於US-A 2007-143876或WO 2005/103266中);品項3272(玉米,品質性狀,寄存為PTA-9972,描述於WO 2006/098952或US-A 2006-230473中);品項40416(玉米,昆蟲控制-耐除草劑,寄存為ATCC PTA-11508,描述於WO 2011/075593中);品項43A47(玉米,昆蟲控制-耐除草劑,寄存為ATCC PTA-11509,描述於WO 2011/075595中);品項5307(玉米,昆蟲控制,寄存為ATCC PTA-9561,描述於WO 2010/077816中);品項ASR-368(剪股穎,耐除草劑,寄存為ATCC PTA-4816,描述於US-A 2006-162007或WO 2004/053062中);品項B16(玉米,耐除草劑,未寄存,描述於US-A 2003-126634中);品項BPS-CV127-9(大豆,耐除草劑,寄存為NCIMB第41603號,描述於WO 2010/080829中);品項CE43-67B(棉花,昆蟲控制,寄存為DSM ACC2724,描述於US-A 2009-217423或WO2006/128573中);品項CE44-69D(棉花,昆蟲控制,未寄存,描述於US-A 2010-0024077中);品項CE44-69D(棉花,昆蟲控制,未寄存,描述於WO 2006/128571中);品項CE46-02A(棉花,昆蟲控制,未寄存,描述於WO 2006/128572中);品項COT102(棉花,昆蟲控制,未寄存,描述於US-A 2006-130175或WO 2004/039986中);品項COT202(棉花,昆蟲控制,未寄存,描述於US-A 2007-067868或WO 2005/054479中);品項COT203(棉花,昆蟲控制,未寄存,描述於WO 2005/054480中);品項DAS40278(玉米,耐除草劑,寄存為ATCC PTA-10244,描述於WO 2011/022469中);品項DAS-59122-7(玉米,昆蟲控制-耐除草劑,寄存為ATCC PTA 11384,描述於US-A 2006-070139中);品項DAS-59132(玉米,昆蟲
控制-耐除草劑,未寄存,描述於WO 2009/100188中);品項DAS68416(大豆,耐除草劑,寄存為ATCC PTA-10442,描述於WO 2011/066384或WO 2011/066360中);品項DP-098140-6(玉米,耐除草劑,寄存為ATCC PTA-8296,描述於US-A 2009-137395或WO 2008/112019中);品項DP-305423-1(大豆,品質性狀,未寄存,描述於US-A 2008-312082或WO 2008/054747中);品項DP-32138-1(玉米,雜交系統,寄存為ATCC PTA-9158,描述於US-A 2009-0210970或WO 2009/103049中);品項DP-356043-5(大豆,耐除草劑,寄存為ATCC PTA-8287,描述於US-A 2010-0184079或WO 2008/002872中);品項EE-1(茄子,昆蟲控制,未寄存,描述於WO 2007/091277中);品項FI117(玉米,耐除草劑,寄存為ATCC 209031,描述於US-A 2006-059581或WO 98/044140中);品項GA21(玉米,耐除草劑,寄存為ATCC 209033,描述於US-A 2005-086719或WO 98/044140中);品項GG25(玉米,耐除草劑,寄存為ATCC 209032,描述於US-A 2005-188434或WO 98/044140中);品項GHB119(棉花,昆蟲控制-耐除草劑,寄存為ATCC PTA-8398,描述於WO 2008/151780中);品項GHB614(棉花,耐除草劑,寄存為ATCC PTA-6878,描述於US-A 2010-050282或WO 2007/017186中);品項GJ11(玉米,耐除草劑,寄存為ATCC 209030,描述於US-A 2005-188434或WO 98/044140中);品項GM RZ13(甜菜,抗病毒性,寄存為NCIMB-41601,描述於WO 2010/076212中);品項H7-1(甜菜,耐除草劑,寄存為NCIMB 41158或NCIMB 41159,描述於US-A 2004-172669或WO 2004/074492中);品項JOPLIN1(小麥,抗病性,未寄存,描述於US-A 2008-064032中);品項LL27(大豆,耐除草劑,寄存為NCIMB41658,描述於WO 2006/108674或US-A 2008-320616中);品項LL55(大豆,耐除草劑,寄存為NCIMB 41660,描述於WO 2006/108675或US-A 2008-196127
中);品項LLcotton25(棉花,耐除草劑,寄存為ATCC PTA-3343,描述於WO 03/013224或US-A 2003-097687中);品項LLRICE06(水稻,耐除草劑,寄存為ATCC-23352,描述於US 6,468,747或WO 00/026345中);品項LLRICE601(水稻,耐除草劑,寄存為ATCC PTA-2600,描述於US-A 2008-2289060或WO 00/026356中);品項LY038(玉米,品質性狀,寄存為ATCC PTA-5623,描述於US-A 2007-028322或WO 2005/061720中);品項MIR162(玉米,昆蟲控制,寄存為PTA-8166,描述於US-A 2009-300784或WO 2007/142840中);品項MIR604(玉米,昆蟲控制,未寄存,描述於US-A 2008-167456或WO 2005/103301中);品項MON15985(棉花,昆蟲控制,寄存為ATCC PTA-2516,描述於US-A 2004-250317或WO 02/100163中);品項MON810(玉米,昆蟲控制,未寄存,描述於US-A 2002-102582中);品項MON863(玉米,昆蟲控制,寄存為ATCC PTA-2605,描述於WO 2004/011601或US-A 2006-095986中);品項MON87427(玉米,授粉控制,寄存為ATCC PTA-7899,描述於WO 2011/062904中);品項MON87460(玉米,抗壓力,寄存為ATCC PTA-8910,描述於WO 2009/111263或US-A 2011-0138504中);品項MON87701(大豆,昆蟲控制,寄存為ATCC PTA-8194,描述於US-A 2009-130071或WO 2009/064652中);品項MON87705(大豆,品質性狀-耐除草劑,寄存為ATCC PTA-9241,描述於US-A 2010-0080887或WO 2010/037016中);品項MON87708(大豆,耐除草劑,寄存為ATCC PTA9670,描述於WO 2011/034704中);品項MON87754(大豆,品質性狀,寄存為ATCC PTA-9385,描述於WO 2010/024976中);品項MON87769(大豆,品質性狀,寄存為ATCC PTA-8911,描述於US-A 2011-0067141或WO 2009/102873中);品項MON88017(玉米,昆蟲控制-耐除草劑,寄存為ATCC PTA-5582,描述於US-A 2008-028482或WO 2005/059103中);品項
MON88913(棉花,耐除草劑,寄存為ATCC PTA-4854,描述於WO 2004/072235或US-A 2006-059590中);品項MON89034(玉米,昆蟲控制,寄存為ATCC PTA-7455,描述於WO 2007/140256或US-A 2008-260932中);品項MON89788(大豆,耐除草劑,寄存為ATCC PTA-6708,描述於US-A 2006-282915或WO 2006/130436中);品項MS11(油菜,授粉控制-耐除草劑,寄存為ATCC PTA-850或PTA-2485,描述於WO 01/031042中);品項MS8(油菜,授粉控制-耐除草劑,寄存為ATCC PTA-730,描述於WO 01/041558或US-A 2003-188347中);品項NK603(玉米,耐除草劑,寄存為ATCC PTA-2478,描述於US-A 2007-292854中);品項PE-7(水稻,昆蟲控制,未寄存,描述於WO 2008/114282中);品項RF3(油菜,授粉控制-耐除草劑,寄存為ATCC PTA-730,描述於WO 01/041558或US-A 2003-188347中);品項RT73(油菜,耐除草劑,未寄存,描述於WO 02/036831或US-A 2008-070260中);品項T227-1(甜菜,耐除草劑,未寄存,描述於WO 02/44407或US-A 2009-265817中);品項T25(玉米,耐除草劑,未寄存,描述於US-A 2001-029014或WO 01/051654中);品項T304-40(棉花,昆蟲控制-耐除草劑,寄存為ATCC PTA-8171,描述於US-A 2010-077501或WO 2008/122406中);品項T342-142(棉花,昆蟲控制,未寄存,描述於WO 2006/128568中);品項TC1507(玉米,昆蟲控制-耐除草劑,未寄存,描述於US-A 2005-039226或WO 2004/099447中);品項VIP1034(玉米,昆蟲控制-耐除草劑,寄存為ATCC PTA-3925.,描述於WO 03/052073中),品項32316(玉米,昆蟲控制-耐除草劑,寄存為PTA-11507,描述於WO 2011/084632中),品項4114(玉米,昆蟲控制-耐除草劑,寄存為PTA-11506,描述於WO 2011/084621中)。
在可藉由本發明之方法控制之植物或作物疾病中,可提及:
白粉病,諸如:例如由禾本科布氏白粉菌(Blumeria graminis)引起之小麥白粉病;例如由白叉絲單囊殼菌(Podosphaera leucotricha)引起之蘋果白粉病(Podosphaera diseases);例如由單絲殼白粉菌(Sphaerotheca fuliginea)引起之瓜類白粉病(Sphaerotheca disease);例如由葡萄白粉病菌(Uncinula necator)引起之葡萄白粉病(Uncinula disease);銹病,諸如:例如由圓柏梨銹病菌(Gymnosporangium sabinae)引起之梨銹病(Gymnosporangium disease);例如由咖啡駝孢鏽菌(Hemileia vastatrix)引起之駝孢銹病(Hemileia disease);例如由豆薯層鏽菌(Phakopsora pachyrhizi)或山馬蝗層鏽菌(Phakopsora meibomiae)引起之層銹病(Phakopsora disease);例如由隱匿柄鏽菌(Puccinia recondite)、禾柄鏽菌(Puccinia graminis)或條形柄鏽菌(Puccinia striiformis)引起之柄鏽菌疾病(Puccinia disease);例如由菜豆銹病菌(Uromyces appendiculatus)引起之菜豆銹病(Uromyces diseases);卵菌病(Oomycete diseases),諸如:例如由白鏽菌(Albugo candida)引起之白銹病(Albugo disease);例如由萵苣露菌病菌(Bremia lactucae)引起之露菌病(Bremia disease);例如由豌豆霜黴菌(Peronospora pisi)或蕓苔根腫菌(P.brassicae)
引起之霜黴病(Peronospora disease);例如由番茄晚疫病菌(Phytophthora infestans)引起之疫黴病(Phytophthora disease);例如由葡萄生單軸黴菌(Plasmopara viticola)引起之單軸黴病(Plasmopara disease);例如由葎草假霜黴菌(Pseudoperonospora humuli)或古巴假霜黴菌(Pseudoperonospora cubensis)引起之假霜黴病(Pseudoperonospora disease);例如由終極腐黴菌(Pythium ultimum)引起之腐黴菌病;葉斑病、葉皰病及葉枯病,諸如:例如由番茄早疫病菌(Alternaria solani)引起之鏈格孢菌病(Alternaria disease);例如由甜菜尾孢菌(Cercospora beticola)引起之尾孢菌病(Cercospora disease);例如由黃瓜黑星病菌(Cladiosporium cucumerinum)引起之黑星病(Cladiosporum disease);例如由禾旋孢腔菌(Cochliobolus sativus)(Conidiaform:內臍蠕孢屬(Drechslera),同義詞:長蠕孢(Helminthosporium)或宮部旋孢腔菌(Cochliobolus miyabeanus)引起之旋孢腔菌屬病;例如由菜豆炭疽病菌(Colletotrichum lindemuthanium)引起之炭疽病(Colletotrichum disease);例如由油橄欖孔雀斑病菌(Cycloconium oleaginum)引起之孔雀斑病(Cycloconium disease);例如由柑桔黑點病菌(Diaporthe citri)引起之黑點病(Diaporthe disease);例如由柑桔痂囊腔菌(Elsinoe fawcettii)引起之痂囊腔菌病
(Elsinoe disease);例如由桃炭疽病菌(Gloeosporium laeticolor)引起之炭疽病(Gloeosporium disease);例如由葡萄晚腐病菌(Glomerella cingulata)引起之晚腐病(Glomerella disease);例如由葡萄球座菌(Guignardia bidwelli)引起之球座菌病(Guignardia disease);例如由十字花科小球腔菌(Leptosphaeria maculans)、穎枯殼小球腔菌(Leptosphaeria nodorum)引起之小球腔菌病(Leptosphaeria disease);例如由稻瘟病菌(Magnaporthe grisea)引起之稻瘟病(Magnaporthe disease);例如由禾生球腔菌(Mycosphaerella graminicola)、落花生球腔菌(Mycosphaerella arachidicola)、斐濟球腔菌(Mycosphaerella fijiensis)引起之球腔菌病(Mycosphaerella disease);例如由小麥穎枯病菌(Phaeosphaeria nodorum)引起之穎枯病(Phaeosphaeria disease);例如由圓核腔菌(Pyrenophora teres)或偃麥草核腔菌(Pyrenophora tritici repentis)引起之核腔菌病(Pyrenophora disease);例如由克樂希柱隔孢菌(Ramularia collocygni)或白斑柱隔孢菌(Ramularia areola)引起之柱隔孢病(Ramularia disease);例如由大麥雲紋病菌(Rhynchosporium secalis)引起之雲紋病(Rhynchosporium disease);例如由芹菜小殼針孢菌(Septoria apii)或番茄殼針孢菌(Septoria lycopercisi)引起之殼針孢病(Septoria disease);例如由肉孢核瑚菌(Typhula incarnata)引起之灰色雪腐病;
例如由蘋果黑星病菌(Venturia inaequalis)引起之黑星病(Venturia disease);根、鞘及莖幹病,諸如:例如由禾穀伏革菌(Corticium graminearum)引起之伏革菌病(Corticium disease);例如由尖孢鐮孢菌(Fusarium oxysporum)引起之鐮孢菌病(Fusarium disease);例如由禾頂囊殼菌(Gaeumannomyces graminis)引起之頂囊殼病(Gaeumannomyces disease);例如由立枯絲核菌(Rhizoctonia solani)引起之絲核菌病;例如由稻帚枝黴(Sarocladium oryzae)引起之葉鞘腐敗病(Sarocladium disease);例如由稻褐色桿腐病菌(Sclerotium oryzae)引起之菌核病(Sclerotium disease);例如由針形眼紋病菌(Tapesia acuformis)引起之眼紋病(Tapesia disease);例如由菸草根腐病菌(Thielaviopsis basicola)引起之根腐病(Thielaviopsis disease);穗及圓錐花序病,諸如:例如由鏈格孢菌屬(Alternaria spp.)引起之鏈格孢菌病;例如由黃麴菌(Aspergillus flavus)引起之麴菌病;例如由枝孢菌屬(Cladosporium spp.)引起之芽枝黴病(Cladosporium disease);例如由麥角菌(Claviceps purpurea)引起之麥角菌病(Claviceps disease);例如由黃色鐮孢菌(Fusarium culmorum)引起之鐮孢菌病;
例如由玉蜀黍赤黴(Gibberella zeae)引起之赤黴菌病;例如由小麥雪黴葉枯病菌(Monographella nivalis)引起之雪黴葉枯病;黑穗病(smut)及黑穗病(bunt disease),諸如:例如由高粱絲黑穗菌(Sphacelotheca reiliana)引起之絲黑穗病(Sphacelotheca disease);例如由小麥網腥黑穗病菌(Tilletia caries)引起之腥黑穗病(Tilletia disease);例如由黑麥桿黑穗病菌(Urocystis occulta)引起之黑穗病(Urocystis disease);例如由大麥散黑穗病菌(Ustilago nuda)引起之黑穗病(Ustilago disease);果腐病(Fruit rot disease)及黴病(mould disease),諸如:例如由黃麴菌(Aspergillus flavus)引起之麴菌病;例如由灰葡萄孢菌(Botrytis cinerea)引起之灰黴病(Botrytis disease);例如由擴展青黴(Penicillium expansum)引起之青黴病;例如由匍枝根黴(Rhizopus stolonifer)引起之根黴病(Rhizopus disease);例如由向日葵核盤菌(Sclerotinia sclerotiorum)引起之核盤菌病(Sclerotinia disease);例如由黃萎輪枝黴(Verticilium alboatrum)引起之輪枝孢病(Verticilium disease);種子及土壤帶有的腐敗病、黴病、萎蔫病、枯病及猝倒病:例如由蕓苔鏈格孢菌(Alternaria brassicicola)引起之鏈格孢菌病;
例如由豌豆絲囊黴(Aphanomyces euteiches)引起之絲囊黴病(Aphanomyces disease);例如由兵豆殼二孢(Ascochyta lentis)引起之殼二孢病(Ascochyta disease);例如由黃麴菌(Aspergillus flavus)引起之麴菌病;例如由多主枝孢(Cladosporium herbarum)引起之枝孢菌病(Cladosporium disease);例如由禾旋孢腔菌(Cochliobolus sativus)引起之旋孢腔菌病;(分生孢子形式:內臍蠕孢屬、平臍蠕孢屬,同義詞:長蠕孢屬)例如由辣椒炭疽病菌(Colletotrichum coccodes)引起之炭疽病;例如由黃色鐮孢菌(Fusarium culmorum)引起之鐮孢菌病;例如由玉蜀黍赤黴(Gibberella zeae)引起之赤黴菌病;例如由菜豆殼球孢菌(Macrophomina phaseolina)引起之殼球孢病(Macrophomina disease);例如由小麥雪黴葉枯病菌引起之雪黴葉枯病;例如由擴展青黴起之青黴病;例如由甘藍莖點黴(Phoma lingam)引起之莖點黴病(Phoma disease);例如由大豆擬莖點黴(Phomopsis sojae)引起之擬莖點黴病(Phomopsis disease);例如由惡疫黴(Phytophthora cactorum)引起之疫黴病(Phytophthora disease);例如由麥類核腔菌(Pyrenophora graminea)引起之核腔菌病;例如由稻梨孢菌(Pyricularia oryzae)引起之梨孢病(Pyricularia disease);例如由終極腐黴菌引起之腐黴菌病;
例如由立枯絲核菌引起之絲核菌病;例如由米根黴(Rhizopus oryzae)引起之根黴病;例如由齊整小菌核(Sclerotium rolfsii)引起之菌核病(Sclerotium disease);例如由穎枯殼針孢(Septoria nodorum)引起之殼針孢病;例如由肉孢核瑚菌引起之灰色雪腐病;例如由大麗輪枝菌(Verticillium dahliae)引起之輪枝菌病(Verticillium disease);潰瘍病(Canker disease)、叢枝病(broom disease)及頂枯病(dieback disease),諸如:例如由仁果幹癌叢赤殼菌(Nectria galligena)引起之叢赤殼病(Nectria disease);枯萎病,諸如:例如由核果鏈核盤菌(Monilinia laxa)引起之鏈核盤菌病(Monilinia disease);葉皰病(Leaf blister disease)或縮葉病(leaf curl disease),諸如:例如由壞損外擔菌(Exobasidium vexans)引起之外擔菌病(Exobasidium disease);例如由畸形外囊菌(Taphrina deformans)引起之外囊菌病(Taphrina disease);木本植物之衰退病(Decline disease),諸如:例如由根黴格孢菌(Phaemoniella clamydospora)引起之埃斯卡病(Esca disease);例如由側彎孢菌(Eutypa lata)引起之葡萄頂枯病(Eutypa dieback);例如由狹長孢靈芝(Ganoderma boninense)引起之靈芝病
(Ganoderma disease);例如由木硬孔菌(Rigidoporus lignosus)引起之硬孔菌病(Rigidoporus disease);花朵及種子疾病,諸如:例如由灰葡萄孢菌(Botrytis cinerea)引起之灰黴病;塊莖疾病,諸如:例如由立枯絲核菌引起之絲核菌病;例如由茄長蠕孢(Helminthosporium solani)引起之長蠕孢病(Helminthosporium disease);根腫病(Club root disease),諸如:例如由蕓苔根腫菌引起之根腫病;由細菌生物引起之疾病,該等細菌生物諸如:黃單胞菌屬(Xanthomonas species),例如水稻白葉枯病菌(Xanthomonas campestris pv.oryzae);假單胞菌屬(Pseudomonas species),例如甜瓜細菌性葉斑病菌(Pseudomonas syringae pv.lachrymans);歐文氏菌屬(Erwinia species),例如解澱粉歐文氏菌(Erwinia amylovora)。
亦可使用本發明之組合物抵抗容易在木料上或木料內部發展之真菌疾病。術語「木料」意謂所有類型之木材種類,及欲用於建構之此木材之所有加工類型,例如緊密材、高密度木板、層壓板及膠合板。根據本發明處理木料之方法主要在於接觸一或多種本發明之化合物或本發明之組合物;此包括例如直接施用、噴霧、浸漬、注射或任何其他適合方式。
在根據本發明之處理方法中通常施用之活性化合物劑量中,對於葉片處理法之施用量一般且有利地為10g/ha至800g/ha,較佳為50
g/ha至300g/ha。就種子處理法而言,所施用之活性物質之劑量一般且有利地為每100kg種子2g至200g,較佳為每100kg種子3g至150g。
咸了解,本文中指示之劑量係提供作為根據本發明方法之說明性實例。熟習此項技術者將知曉如何調整施用劑量,尤其根據待處理之植物或作物之性質調整。
本發明之化合物或混合物亦可用於製備適用於治癒性或預防性治療人類或動物真菌疾病之組合物,該等真菌疾病諸如黴菌病、皮膚病、毛癬菌病及念珠菌病或由麴菌屬(例如薰煙色麴菌(Aspergillus fumigatus))所導致之疾病。
本發明進一步關於如本文所定義之式(I)化合物用於控制植物病原性真菌之用途。
本發明進一步關於如本文所定義之式(I)化合物用於處理轉殖基因植物之用途。
本發明進一步關於如本文所定義之式(I)化合物用於處理種子及轉殖基因植物之種子的用途。
本發明進一步關於一種用於產生用於控制植物病原性有害真菌之組合物的方法,其特徵在於如本文所定義之式(I)衍生物與增量劑及/或界面活性劑混合。
現將參考下表之化合物實例及以下製備或功效實例來說明本發明之各個態樣。
表1以非限制性方式說明本發明之式(I)化合物之實例:
(I)
在表1中,除非另外說明,否則M+H(ApcI+)意謂如在經由正型大氣壓化學電離之質譜分析中所觀測之分子離子峰加1a.m.u.(原子質量單位)。
在表1中,logP值係根據EEC Directive 79/831 Annex V.A8,藉由HPLC(高效液相層析)在逆相管柱(C 18)上,使用以下所述方法測定:溫度:40℃;移動相:0.1%水性甲酸及乙腈;線性梯度:10%乙腈至90%乙腈。
使用具有已知logP值(在兩個連續烷酮之間使用線性內插法藉由滯留時間測定logP值)之未分支烷-2-酮(包含3至16個碳原子)進行校準。使用200nm至400nm之UV光譜及層析信號之峰值測定λ最大值。
表2以非限制性方式說明本發明之式(I)化合物之實例:
其中Z4及其鄰接取代基X與其所連接之碳原子一起可形成經取代或未經取代之C4-C7環烷基。
在表2中,M+H(ApcI+)及logP如表1所定義。
表3以非限制性方式說明本發明之式(II)化合物之實例,
在表3中,M+H(ApcI+)及logP如表1所定義。
表4以非限制性方式說明本發明式(IV)化合物之實例,
在表4中,M+H(ApcI+)及logP如表1所定義。
表5以非限制性方式說明本發明之式(V)化合物之實例,
其中U2表示鹵素原子。
在表5中,M+H(ApcI+)及logP如表1所定義。
表6提供表1至表4之所選編號之化合物之NMR數據(1H)。
所選實例之1H-NMR資料以1H-NMR峰清單形式陳述。對於各信號峰,所列δ值以ppm表示且信號強度以括號表示。
尖銳信號之強度與印刷之NMR光譜實例中之信號高度(cm)相關且顯示信號強度之真實關係。自寬信號,可顯示信號之若干峰值或中間值及其相比於光譜中之最密集信號之相對強度。
1H-NMR峰清單類似於經典1H-NMR印刷圖且因此通常含有經典NMR說明中所列之所有峰。另外,其可如古典1H-NMR印刷一樣顯示
溶劑信號、目標化合物之立體異構體(其亦為本發明之目的)及/或雜質之峰。為了在溶劑及/或水之δ範圍(delta-range)中顯示化合物信號,常用溶劑之峰(例如DMSO於DMSO-d6中之峰)及水之峰顯示在吾人之1H-NMR峰清單中且通常平均具有較高強度。
目標化合物之立體異構體之峰及/或雜質峰通常平均具有比目標化合物(例如純度>90%)之峰低之強度。此類立體異構體及/或雜質對於特定製備方法可為典型的。因此,其峰可經由「副產物指紋」幫助識別吾人之製備方法之再現。
用已知方法(MestreC、ACD模擬以及用憑經驗評估之期望值)計算目標化合物之峰之專家可視情況使用額外強度過濾器根據需要分離目標化合物之峰。此分離將類似於古典1H-NMR解釋下之相關峰挑選。
具有峰清單之NMR資料描述之其他細節可見於研究公開資料庫第564025號之公開案「Citation of NMR Peaklist Data within Patent Applications」中。
以下實例以非限制性方式說明本發明之式(I)化合物之製備及功效。
向7.34g(20.56mmol)溴化甲基三苯基鏻於25mL四氫呋喃中之經冷卻懸浮液中緩慢添加20.56ml(20.56mmol)1M第三丁醇鉀於四氫呋喃中之溶液。在0℃下攪拌反應混合物20分鐘。在0℃下添加4g(17.13mmol)1-(2-溴-4-氯苯基)乙酮於20mL四氫呋喃中之溶液且在室溫下進一步攪拌反應混合物15小時。反應混合物藉由NH4Cl飽和水溶液稀釋且藉由乙酸乙酯萃取。有機相藉由水洗滌,經硫酸鎂乾燥,真空濃縮且藉由矽膠管柱層析(梯度正庚烷/乙酸乙酯)純化獲得3.54g(84%產率)呈油狀之2-溴-4-氯-1-(丙-1-烯-2-基)苯(M=230,藉由GC-質譜)。LogP=4.91。
在氬氣下,在0℃下,向21.94ml(21.94mmol)1M二乙基鋅於己烷中之溶液中緩慢添加2.5g(21.94mmol)三氟乙酸於10mL二氯甲烷中之溶液。在0℃下攪拌反應混合物20分鐘。接著添加5.87g(21.94mmol)二碘甲烷於10mL二氯甲烷中之溶液且反應混合物在0℃下進一步攪拌20分鐘。最終添加2.54g(10.97mmol)2-溴-4-氯-1-(丙-1-烯-2-基)苯於10mL二氯甲烷中之溶液且在室溫下攪拌反應混合物2小時。反應混合物藉由70mL 1N HCl水溶液稀釋且藉由3×70mL乙酸乙酯萃取。有機相藉由NaCl飽和水溶液洗滌,經硫酸鎂乾燥,真空濃縮且藉由矽膠管柱層析(正庚烷)純化獲得2.65g(93%產率)呈無色油狀之2-溴-4-氯-1-(1-甲基環丙基)苯(M=244,藉由GC-質譜)。LogP=4.93。
在-78℃下,在氬氣下,向1g(4.07mmol)2-溴-4-氯-1-(1-甲基環丙基)苯於10mL無水四氫呋喃中之溶液中緩慢添加1.8mL(4.48mmol)1.6M BuLi於己烷中之溶液。反應混合物在-78℃下攪拌45分鐘,接著藉由0.38mL(4.89mmol)無水DMF淬滅且在-78℃下再靜置3小時。將反應混合物倒在1N HCl水溶液上且藉由乙酸乙酯萃取。有機相藉由水洗滌,經硫酸鎂乾燥,真空濃縮且藉由矽膠管柱層析(梯度正庚烷/乙酸乙酯)純化獲得0.46g(55%產率)呈無色油狀之5-氯-2-(1-甲基環丙基)苯甲醛(M-CHO=166,藉由GC-質譜)。
向0.47g(8.22mmol)環丙胺及2g 3Å分子篩於15mL甲醇中之經冷卻溶液中依序緩慢添加0.62g(10.3mmol)乙酸、0.80g(4.11mmol)5-氯-2-(1-甲基環丙基)苯甲醛。在80℃下攪拌反應混合物3小時。接著將反應混合物冷卻至室溫且緩慢添加0.39g(6.17mmol)氰基硼氫化鈉。在80℃下進一步攪拌反應混合物2小時。接著經矽藻土濾料過濾經冷卻之反應混合物且藉由甲醇洗滌濾餅。濃縮,留下淡黃色固體殘餘物,將其藉由乙酸乙酯溶解,藉由1N氫氧化鈉水溶液,隨後NaCl飽和水溶液洗滌。乾燥且真空濃縮有機相獲得0.85g(83%產率)呈黃色油狀之N-[5-氯-2-(1-甲基環丙基)苯甲基]環丙胺(M+H=236)。
在乾燥之RadleysTM小瓶中,將128mg(0.66mmol)3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯於2mL無水四氫呋喃中之溶液添加至141mg(0.60mmol)N-[5-氯-2-(1-甲基環丙基)苯甲基]環丙胺及0.1mL(0.72mmol)三乙胺於3mL無水四氫呋喃中之混合物中。在回流下加熱反應混合物120分鐘。冷卻後,添加幾毫升水且藉由乙酸乙酯萃取反應混
合物。有機相藉由NaCl飽和水溶液洗滌,經ChemElutTM濾筒乾燥,濃縮且藉由矽膠管柱層析(梯度正庚烷/乙酸乙酯)純化獲得185mg(74%產率)呈無色油狀之N-[5-氯-2-(1-甲基環丙基)苯甲基]-N-環丙基-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺(M+H=394)。
在RadleysTM小瓶中,將1g(3.22mmol)2-(溴甲基)-1-[1-(二氟甲基)環丙基]-4-氟苯添加至3.5mL環丙胺中且在室溫下攪拌2小時。真空移除過量環丙胺。向殘餘物中添加2mL水且藉由3×2mL二氯甲烷萃取反應混合物。乾燥且真空濃縮有機萃取物獲得690mg粗物質。藉由矽膠管柱層析(梯度正庚烷/乙酸乙酯)純化獲得450mg(52%產率)呈油狀之N-{2-[1-(二氟甲基)環丙基]-5-氟苯甲基}環丙胺(M+H=256)。LogP=1.08。
在乾燥之RadleysTM小瓶中,將80mg(0.41mmol)3-(二氟甲基)-1-甲基-1H-吡唑-4-羰基氯於2mL無水四氫呋喃中之溶液添加至100mg(0.39mmol)N-{2-[1-(二氟甲基)環丙基]-5-氟苯甲基}環丙胺及0.06mL(0.43mmol)三乙胺於3mL無水四氫呋喃中之混合物中。在室溫下攪拌反應混合物隔夜。反應混合物經氧化鋁鹼性濾筒過濾且藉由幾毫升四氫呋喃洗滌若干次。真空濃縮且藉由製備型HPLC(梯度乙腈/水+0.1% HCO2H)純化殘餘物獲得138mg(81%產率)呈油狀之N-環丙基-3-(二氟-甲基)-N-{2-[1-(二氟甲基)環丙基]-5-氟苯甲基}-1-甲基-1H-吡唑-4-甲醯胺(M+H=414)。LogP=3.09。
稱量0.27mmol五硫化磷(P2S5),放入13mL ChemspeedTM小瓶中。添加3mL 0.18M醯胺(I)(0.54mmol)於二噁烷中之溶液,且在回流下加熱混合物兩小時。隨後使溫度冷卻至80℃且添加2.5mL水。在80℃下再加熱混合物1小時。隨後添加2mL水且用4mL二氯甲烷將反應混合物萃取兩次。使有機相沈積在鹼性氧化鋁濾筒(2g)上且用8mL二氯甲烷溶離兩次。移除溶劑且藉由LCMS及NMR分析粗硫代醯胺衍生物。藉由製備型LC將不夠純之化合物進一步純化。
溶劑:5體積%二甲亞碸
10體積%丙酮
乳化劑:1μL Tween® 80/mg活性成分
使活性成分在二甲亞碸/丙酮/Tween® 80之混合物中溶解且均質化隨後在水中稀釋至所需濃度。
藉由噴灑如上所述製備之活性成分處理小麥之幼小植物。對照植物僅用丙酮/二甲亞碸/Tween® 80之水溶液來處理。
在24小時之後,藉由對葉子噴灑隱匿柄鏽菌孢子之水性懸浮液污染植物。使經污染之小麥在20℃下且在100%相對濕度下培育24小時,且隨後在20℃下且在70-80%相對濕度下培育10天。
在接種11天之後評估測試。0%意謂對應於對照植物之功效而100%之功效意謂未觀察到疾病。
在此測試中,本發明之以下化合物在100ppm活性成分之濃度下顯示70%至79%功效:I.089;I.115;I.117;I.118;Ia.03
在此測試中,本發明之以下化合物在100ppm活性成分之濃度下顯示80%至89%功效:I.006;I.007;I.008;I.010;I.013;I.020;
I.022;I.025;I.034;I.036;I.053;I.056;I.063;I.064;I.070;I.071;I.073;I.083;I.086;I.088;I.090;I.097;I.107;I.112;I.123;I.125;I.138;I.140;I.145;I.147;I.150;I.153;Ia.01;Ia.02
在此測試中,本發明之以下化合物在100ppm活性成分之濃度下顯示90%至100%功效:I.003;I.004;I.005;I.009;I.011;I.014;I.015;I.016;I.017;I.018;I.019;I.023;I.024;I.026;I.027;I.028;I.029;I.030;I.031;I.032;I.033;I.037;I.038;I.040;I.041;I.042;I.043;I.046;I.048;I.050;I.052;I.054;I.065;I.067;I.068;I.069;I.074;I.075;I.076;I.077;I.078;I.079;I.080;I.081;I.082;I.084;I.085;I.087;I.092;I.093;I.094;I.095;I.096;I.098;I.099;I.102;I.103;I.105;I.106;I.108;I.113;I.114;I.116;I.119;I.121;I.122;I.124;I.131;I.135;I.136;I.137;I.139;I.141;I.143;I.144;I.149;I.152
在相同條件下,在100ppm活性成分與實例I.067之化合物的劑量下觀測到極佳(至少98%)保護,而如表A1中的專利申請案WO-2012/052490中揭示之實例65及66之化合物(未經取代之醯胺)未觀測到保護:
國際專利WO-2012/052490中揭示之化合物65對應於N-(2-環丙基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺,及
國際專利WO-2012/052490中揭示之化合物66對應於5-氯-N-(2-環-丙基苯甲基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺。
此等結果顯示本發明化合物具有比WO-2012/052490中所揭示之結構上最接近之化合物好得多的生物活性。
溶劑:5體積%二甲亞碸
10體積%丙酮
乳化劑:1μL Tween® 80/mg活性成分
使活性成分在二甲亞碸/丙酮/Tween® 80之混合物中溶解且均質化隨後在水中稀釋至所需濃度。
豆之幼小植物係藉由噴灑如上文所描述製備之活性成份來處理。對照植物僅用丙酮/二甲亞碸/Tween® 80之水溶液來處理。
在24小時之後,藉由用菜豆銹病菌孢子之水性懸浮液噴灑葉子來污染植物。使經污染之豆植物在20℃下且在100%相對濕度下培育24小時,且隨後在20℃下且在70-80%相對濕度下培育10天。
在接種11天之後評估測試。0%意謂對應於對照植物之功效而100%之功效意謂未觀察到疾病。
在此測試中,本發明之以下化合物在100ppm活性成分之濃度下顯示70%至79%功效:I.002;I.008;I.071;I.072;I.077;I.097;I.126;I.128
在此測試中,本發明之以下化合物在100ppm活性成分之濃度下顯示80%至89%功效:I.001;I.034;I.046;I.056;I.067;I.088;I.115;I.145;I.152
在此測試中,本發明之以下化合物在100ppm活性成分之濃度下顯示90%至100%功效:I.003;I.004;I.005;I.006;I.009;I.010;I.011;I.013;I.014;I.015;I.016;I.017;I.018;I.019;I.022;
I.023;I.024;I.026;I.027;I.028;I.029;I.030;I.031;I.032;I.033;I.036;I.037;I.038;I.040;I.041;I.042;I.048;I.050;I.052;I.063;I.064;I.065;I.068;I.069;I.070;I.073;I.074;I.075;I.076;I.078;I.079;I.080;I.081;I.082;I.084;I.085;I.086;I.087;I.092;I.093;I.094;I.095;I.096;I.099;I.102;I.103;I.105;I.106;I.107;I.108;I.109;I.112;I.113;I.114;I.116;I.119;I.120;I.121;I.122;I.123;I.124;I.127;I.131;I.135;I.136;I.137;I.138;I.139;I.140;I.141;I.143;I.144;I.147;I.149;I.150
在相同條件下,在10ppm活性成分與實例I.029及1.033之化合物的劑量下觀測到相對於總保護之極佳(至少90%)保護,而如表B1中的專利申請案WO-2007/087906中揭示之實例399之化合物(環己基類似物)未觀測到保護:
國際專利WO-2007/087906中揭示之化合物399對應於N-(2-環己基苯甲基)-N-環丙基-5-氟-1,3-二甲基-1H-吡唑-4-甲醯胺。
此等結果顯示本發明化合物具有比WO-2007/087906中所揭示之結構上最接近之化合物好得多的生物活性。
溶劑:24.5重量份丙酮
24.5重量份N,N-二甲基乙醯胺
乳化劑:1重量份烷基芳基聚二醇醚
為了製造適合活性化合物製劑,將1重量份活性化合物與所述量
之溶劑及乳化劑混合,且用水將濃縮物稀釋至所需濃度。
為了測試預防性活性,以規定施用速率用活性化合物製劑噴灑幼小植物。在噴灑塗層乾燥之後,對植物接種引起大豆銹病(豆薯層鏽菌)之水性孢子懸浮液,且隨後在約24℃及95%之相對大氣濕度下的培育箱中無光靜置24小時。
植物保持於約24℃且相對大氣濕度為約80%且日/夜間隔為12小時的培育箱中。
在接種7天之後評估測試。0%意謂對應於未處理之對照組的功效,而100%之功效意謂未觀測到疾病。
在此測試中,本發明之以下化合物在10ppm活性成分之濃度下顯示70%至79%功效:I.016;I.050;I.087
在此測試中,本發明之以下化合物在10ppm活性成分之濃度下顯示80%至89%功效:I.093;I.113
在此測試中,本發明之以下化合物在10ppm活性成分之濃度下顯示90%至100%功效:I.040
在相同條件下,在10ppm活性成分與實例I.040及1.113之化合物的劑量下觀測到相對於總保護之高(至少80%)至極佳(至少90%)保護,而如表C1中的專利申請案WO-2010/130767中揭示之實例47及123之化合物(雙去氟類似物)觀測到差(小於30%)至無保護:
國際專利WO-2010/130767中揭示之化合物47對應於N-環丙基-N-(2-環丙基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺,及國際專利WO-2010/130767中揭示之化合物123對應於N-環丙基-
N-(2-環丙基-5-氟苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺。
此等結果顯示本發明化合物具有比WO-2010/130767中所揭示之結構上最接近之化合物好得多的生物活性。
在相同條件下,在10ppm活性成分與實例I.087之化合物的劑量下觀測到相對於總保護之良好(至少70%)保護,而如表C2中的專利申請案WO-2010/130767中揭示之實例41之化合物(雙去氟類似物)未觀測到保護:
國際專利WO-2010/130767中揭示之化合物41對應於N-(5-氯-2-環丙基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺。
此等結果顯示本發明化合物具有比WO-2010/130767中所揭示之結構上最接近之化合物好得多的生物活性。
Claims (22)
- 一種式(I)化合物
- 如請求項1之化合物,其中A係選自由以下組成之清單:式(A1)之雜環
- 如請求項2之化合物,其中A係選自由A2;A3;A5;A6;A10及A13組成之清單。
- 如請求項3之化合物,其中A表示A13,其中R34表示經取代或未經取代之C1-C5烷基、包含多達9個可相同或不同之鹵素原子之C1-C5鹵代烷基;經取代或未經取代之C1-C5烷氧基;R35表示氫原子或鹵素原子且R36表示經取代或未經取代之C1-C5烷基。
- 如請求項4之化合物,其中A表示A13,其中R34表示C1-C5烷基、包含多達3個可相同或不同之鹵素原子之C1-C5鹵代烷基;R35表示氫原子;氯原子;或氟原子;且R36表示甲基。
- 如請求項1至5中任一項之化合物,其中T表示O。
- 如請求項1至6中任一項之化合物,其中Z1表示經取代或未經取代之環丙基。
- 如請求項7之化合物,其中Z1表示未經取代之環丙基或C1-C5烷基環丙基。
- 如請求項1至8中任一項之化合物,其中Z2及Z3獨立地表示氫原子或甲基。
- 如請求項1至9中任一項之化合物,其中p表示1、3或4。
- 如請求項1至10中任一項之化合物,其中Z4表示鹵素、經取代或未經取代之C1-C4烷基、具有1至3個鹵素原子之C1-C4鹵代烷基、經取代或未經取代之C1-C4烷基氧基、經取代或未經取代之環丙基、經取代或未經取代之C2-C4烯基或經取代或未經取代之C2-C4炔基。
- 如請求項11之化合物,其中Z4表示氯、甲基、乙基、丙基、異丙基、異丁基、環丙基、甲氧基、甲氧基甲基、二氟甲基、三氟 甲基或乙炔基。
- 如請求項1至12中任一項之化合物,其中X獨立地表示鹵素原子;經取代或未經取代之C1-C8烷基;包含多達9個可相同或不同之鹵素原子之C1-C8鹵代烷基;經取代或未經取代之C2-C8烯基;經取代或未經取代之C5-C7環烯基;經取代或未經取代之C3-C7環烷基;三(C1-C8烷基)矽烷基;經取代或未經取代之C1-C8烷氧基;經取代或未經取代之C1-C8烷基硫基;經取代或未經取代之苯基;經取代或未經取代之噻吩基或經取代或未經取代之呋喃基。
- 如請求項1至13中任一項之化合物,其中Y獨立地表示鹵素或經取代或未經取代之C1-C8烷基。
- 一種式(II)化合物以及其可接受之鹽:
- 一種式(IV)化合物:
- 一種式(V)化合物,
- 如請求項17之化合物,其限制條件為化合物(V)進一步不代表1-[2-(氯甲基)-4,5-二甲氧基苯基]環戊烷甲腈。
- 一種殺真菌劑組合物,其包含有效量之如請求項1至14中任一項的式(I)化合物作為活性成分及農業上可接受之載體、載劑或填充劑。
- 一種控制作物之植物病原性真菌之方法,其特徵在於將農藝學上有效且實質上無植物毒性量之如請求項1至14中任一項之化合物或如請求項19之組合物施用於植物生長或能夠生長之土壤、 植物之葉子及/或果實或植物之種子。
- 一種製造用於控制植物病原性有害真菌之組合物之方法,其特徵在於將如請求項1至14中任一項之式(I)衍生物與增量劑及/或界面活性劑混合。
- 一種如請求項1至14中任一項之式(I)化合物或如請求項19之組合物的用途,其用於控制植物病原性有害真菌或用於處理植物、種子、轉殖基因植物或轉殖基因種子。
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- 2014-12-04 US US15/101,380 patent/US10071967B2/en not_active Expired - Fee Related
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- 2014-12-04 TW TW103142233A patent/TW201607929A/zh unknown
- 2014-12-04 CN CN201480066700.9A patent/CN105873907B/zh not_active Expired - Fee Related
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AR098627A1 (es) | 2016-06-01 |
CN105873907B (zh) | 2019-03-12 |
EP3077377B1 (en) | 2020-01-22 |
US10071967B2 (en) | 2018-09-11 |
US20160326120A1 (en) | 2016-11-10 |
EP3077377A1 (en) | 2016-10-12 |
CN105873907A (zh) | 2016-08-17 |
WO2015082587A1 (en) | 2015-06-11 |
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