TW201900630A - 4-胺基-6-(雜環)吡啶甲酸酯及6-胺基-2-(雜環)嘧啶-4-羧酸酯以及其作為除草劑的用途 - Google Patents
4-胺基-6-(雜環)吡啶甲酸酯及6-胺基-2-(雜環)嘧啶-4-羧酸酯以及其作為除草劑的用途 Download PDFInfo
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- alkoxy
- alkynyl
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- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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- 239000004562 water dispersible granule Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Abstract
4-胺基-6-(雜環)吡啶甲酸酯及其衍生物;6-胺基-2-(雜環)嘧啶-4-羧酸酯及其衍生物;以及將其用作除草劑的方法。
Description
本申請案係請求於2017年5月10日提申之美國臨時專利申請案第62/504,148號之權益,其全文係以引用方式明確併入本文中。
本案揭露內容包括除草化合物、含有相同化合物的組成物、以及以這類化合物及組成物控制非所欲的植被之方法。
出現非所欲的植被,例如雜草,是農民在作物中、牧場裡以及其他環境下常常要面對的問題。雜草會和作物競爭,對於作物的產量有負面的影響。化學除草劑的使用,是在控制非所欲的植被時一個很重要的工具。地膚和虞美人(common poppy)這種非所欲的植被,對種植作物的田地(例如小麥、大麥、玉米、燕麥、油菜和甜菜)、牧場、路邊、荒地以及溝渠邊上來說特別的困擾。
舉例來說,地膚(Kochia scoparia)是一種早期出現的夏季一年生物種,常見於美國西岸與加拿大。其為一種草本的雙子葉植物,是藜科家族的一員。由於地膚在夏季晚期和秋天時為紅色,其被作為一種觀賞 植物從歐洲引進至北美。地膚(Kochia scoparia(L.)Schrad.)對北美大平原(NGP)的農地、牧場、路邊、荒地以及溝渠邊上而言,是最棘手的一年生闊葉雜草之一。如果沒有及早控制,地膚會造成作物的產量嚴重衰減(最高可達60%),這包括小麥、大麥、玉米和甜菜在內,且在化學休耕期間其會是最主要的問題雜草。
種子從少有休眠到完全沒有休眠,而大部分(>90%)在土壤表面上或者周邊的種子在免耕的條件下,會於春季的早期發芽,經過夏季會出現2次至3次的抽梢。地膚在夏季晚期會呈現快速的生長以及開花。此種雜草可以自花授粉以及交互授粉,並以種子繁殖。單一株地膚就能夠產生高達50,000顆種子,種子可以藉由風、水、乾草中的汙染物、農業用的器械或是農場內的車輛來傳播。在成熟期時,植物會在莖的根部裂開,並且藉由盛行風"滾"過陸地上,這是一種很獨特且很快速的種子散播機制。此外,地膚很能適應乾旱、高鹽度、炎熱以及寒冷的條件。
已被用來試圖控制地膚的除草劑包括抑制乙醯乳酸合成酶(ALS)的除草劑、氯氟吡氧乙酸(fluroxypyr)、汰克草(dicamba)以及嘉磷塞(glyphosate)。氯氟吡氧乙酸和汰克草是有選擇性的除草劑,能夠控制闊葉雜草,且一般不會傷害到禾本科植物。常被施用於控制地膚的(2-二氯苯氧基)乙酸(2,4-D),並不是很有效。
嘉磷塞(諸如Roundup®,其為德拉瓦州的股份有限公司孟山都科技(Monsanto Technology LLC)之註冊商標,或其他類似的學名藥)是一種用在雜草控制,無選擇性、廣泛有效的除草劑。然而,為了要在種植前、化學休耕期間,以及於作物種植期間施用在Roundup Ready®(同為孟山都科技股份有限公司的註冊商標)作物上,作到雜草除盡(burndown)的控制,已經有許多和使用嘉磷塞超過十年有關的因子,造成對嘉磷塞有抗性的雜 草出現(目前在美國有24種),其中包括地膚。例如已有可抗三嗪類、生長素、ALS除草劑、以及嘉磷塞的地膚生物型被詳細記載在案。
在冬季穀物中生長的穀物罌粟花(corn poppy)或虞美人(Papaver rhoeas),是在地中海氣候的南歐地區中最棘手的雙子葉雜草之一。穀物罌粟花是很有競爭性的雜草,因其降低穀物產量的能力而聲名遠播。此品種在穀物農地的入侵、生長和存留能力,可歸因於高耐性種子庫的形成、發芽期間的延長,以及種子產量很高所導致。由於罌粟科植物(poppy)其抗除草劑生物型的傳播,對於穀物種植者以及歐洲權責單位而言,管理罌粟科植物已經是一個嚴重且日益增加的挑戰。在比利時、丹麥、法國、德國、希臘、義大利、西班牙、瑞典和英國,皆有通報發現對硫醯脲類除草劑及/或生長素類的除草劑有抗性的虞美人(P.rhoeas)族群。在波蘭,已發現部分可抗光合系統II(PSII)抑制除草劑的虞美人(P.rhoeas)族群。可抗除草劑的虞美人(P.rhoeas)生物型的傳播,對穀物生產系統的生產效益是一大威脅。
因此,仍然需要有新型的化學除草劑,能作到更廣泛的控制雜草、具有選擇性、對穀物傷害小、具貯存安定性、操作容易、對抗雜草的活性更高,及/或需要對傳統除草劑產生除草劑耐性的解決方式。
本案提供化學式(I)的化合物:
其中X為N或CY,其中Y為氫、鹵素、C1-C3烷基、C1-C3鹵烷基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3烷氧基、C1-C3硫烷基或C1-C3鹵基硫烷基;R1為經CN取代之C3-C12炔基或C1-C3烷基;R2為鹵素、C1-C4烷基、C1-C4鹵烷基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C4烷氧基、C1-C4鹵烷氧基、C1-C4硫烷基、C1-C4鹵基硫烷基、胺基、C1-C4烷胺基、C2-C4鹵烷胺基、甲醯基、C1-C3烷基羰基、C1-C3鹵烷羰基、氰基或式-CR17=CR18-SiR19R20R21的基團,其中R17為氫、F或Cl;R18為氫、F、Cl、C1-C4烷基或C1-C4鹵烷基;且R19、R20及R21獨立地為C1-C10烷基、C3-C6環烷基、苯基、經取代苯基、C1-C10烷氧基或OH;R3及R4獨立地為氫、C1-C6烷基、C1-C6鹵烷基、C3-C6烯基、C3-C6鹵烯基、C3-C6炔基、甲醯基、C1-C3烷基羰基、C1-C3鹵烷羰基、C1-C6烷氧基羰基、C1-C6烷胺甲醯基、C1-C6烷基磺醯基、C1-C6三烷基矽基、C1-C6雙烷膦醯基,或R3和R4與N相連共同為一5元或6元飽和環,或R3和R4共同代表=CR3' (R4' ),其中R3' 及R4' 獨立地為氫、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷胺基,或R3' 和R4' 與=C相連共同代表一5元或6元飽和環;R5為氫、鹵素、C1-C4烷基、C1-C4鹵烷基、環烷基、鹵基環烷基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3硫烷基、C1-C3鹵基硫烷基、胺基、C1-C4烷胺基、C2-C4鹵烷胺基、OH或CN;R6及R6' 獨立地為氫、鹵素、C1-C4烷基、C1-C4鹵烷基、環丙基、鹵基環丙基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3硫烷基、C1-C3鹵基硫烷基、胺基、C1-C4烷胺基或C2-C4鹵烷胺基、OH、CN或NO2; R7及R7' 獨立地為氫、鹵素、C1-C4烷基、C1-C4鹵烷基、環丙基、鹵基環丙基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3硫烷基、C1-C3鹵基硫烷基、胺基、C1-C4烷胺基、C2-C4鹵烷胺基或苯基;R8為氫、C1-C6烷基、C1-C6鹵烷基、C3-C6烯基、C3-C6鹵烯基、C3-C6炔基、甲醯基、C1-C6烷基羰基、C1-C6環烷基羰基、C1-C6鹵烷羰基、C1-C6烷氧基羰基、C1-C6鹵烷氧基羰基、芳羰基、雜芳羰基、C1-C6烷胺甲醯基、C1-C6硫烷基、C1-C6烷基磺醯基、C1-C6鹵烷基磺醯基、芳基磺醯基、C1-C6三烷基矽基、胺基、C1-C4烷胺基、氰基或苯基,或其N-氧化物。
本案也提供一種控制非所欲的植被之方法,包括提供式(I)的化合物並且(a)接觸非所欲的植被,或接觸非所欲的植被的鄰接區域或(b)在萌前(pre-emergently)讓土壤或水接觸一除草有效量之至少一式(I)化合物或其農業上可接受之衍生物。
如本說明書中所使用,「除草劑」與「除草活性成分」,在以適當劑量施用時,可被理解為其包括一控制非所欲的植被的化合物。
如本說明書中所使用,「非所欲植被的控制」,或是「控制非所欲的植被」,表示是殺死植被或防止植被出現,或是對植被造成一些其他負面的修改效果例如讓植被偏離自然的生長或發展、調節、脫水、遲緩及類似效果。
如本說明書中所使用,「除草有效量或者植被控制量」,可 被理解為包括除草活性成分的劑量,其之施用可控制相關的非所欲植被。
如本說明書中所使用,「施用除草劑或除草組成物」,可被理解為包括直接將其投予目標的植被,或者投至其所在地,或是投藥至想要控制非所欲的植被之區域。作為示例用的施用方法包括但不限於,在萌前接觸土壤或水、在萌後(post-emergently)接觸非所欲的植被或者非所欲的植被之鄰接區域。
如本說明書中所使用,「植物」與「植被」可包含但不限於休眠中的種子、發芽的種子、新生的幼苗、從營養繁殖體(vegetative propagules)新生的植物、未成熟的植被及已成長的植被。
如本說明書中所使用,「未成熟的植被」可被理解為包括繁殖期前的小型營養生長植物,而成熟的植被指的是在繁殖期間與繁殖期後的營養生長植物。
如本說明書中所使用,除非另有指明,「醯基」指的是甲醯基、C1-C3烷基羰基與C1-C3鹵烷羰基。「C1-C6醯基」指的是甲醯基、C1-C5烷基羰基與C1-C5鹵烷羰基(此基團含有總數為1到6的碳原子)。
如本說明書中所使用,「烷基」指的是飽和的、直鏈或分支的飽和烴分子部分。除非另有指明,否則意指的是C1-C10烷基。實例包括但不限於:甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基-丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基-丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基-丙基。
如於本說明書中所使用,「鹵烷基」指的是直鏈或分支的烷基,在這些基團中氫原子可部分或完全被鹵原子取代。除非另有指明,否則意指的是C1-C8基團。實例包括氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟-甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基和1,1,1-三氟丙-2-基。
如於本說明書中所使用,「烯基」指的是含有雙鍵之不飽和的、直鏈的,或分支的烴分子部分(moieties)。除非另有指明,否則意指的是C2-C8烯基。烯基可包含一個以上的不飽和鍵。實例包括乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁 烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基。乙烯基指的是具有-CH=CH2結構的基團;1-丙烯基指的是具有-CH=CH-CH3結構的基團;而2-丙烯基指的是具有-CH2-CH=CH2結構的基團。
如於本說明書中所使用,「炔基」代表含有三鍵之直鏈或分支的烴分子部分。除非另有指明,否則意指的是C2-C8炔基。炔基可包含一個以上的不飽和鍵。實例包括C2-C6-炔基,如乙炔基、1-丙炔基、2-丙炔基(或炔丙基)、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、3-甲基-1-丁炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、3-甲基-1-戊炔基、4-甲基-1-戊炔基、1-甲基-2-戊炔基、4-甲基-2-戊炔基、1-甲基-3-戊炔基、2-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基。
如於本說明書中所使用,「烷氧基」指的是化學式為R-O-的基團,其中R是如上文定義的烷基。除非另有指明,否則意指的是其中的R為C1-C8烷基的烷氧基。實例包括甲氧基、乙氧基、丙氧基、1-甲基-乙氧基、丁氧基、1-甲基-丙氧基、2-甲基-丙氧基、1,1-二甲基-乙氧基、戊氧基、1-甲基-丁氧基、2-甲基-丁氧基、3-甲基-丁氧基、2,2-二甲基-丙氧基、1-乙基-丙氧基、己氧基、1,1-二甲基-丙氧基、1,2-二甲基-丙氧基、1- 甲基-戊氧基、2-甲基-戊氧基、3-甲基-戊氧基、4-甲基戊氧基、1,1-二甲基-丁氧基、1,2-二甲基-丁氧基、1,3-二甲基-丁氧基、2,2-二甲基-丁氧基、2,3-二甲基-丁氧基、3,3-二甲基-丁氧基、1-乙基-丁氧基、2-乙基丁氧基、1,1,2-三甲基-丙氧基、1,2,2-三甲基-丙氧基、1-乙基-1-甲基-丙氧基和1-乙基-2-甲基-丙氧基。
如於本說明書中所使用,「鹵烷氧基」指的是化學式為R-O-的基團,其中R是如上文定義的鹵烷基。除非另有指明,否則意指的是其中的R為C1-C8烷基的鹵烷氧基。實例包括氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基和1,1,1-三氟丙-2-氧基。
如於本說明書中所使用,「硫烷基」指的是化學式為R-S-的基團,其中R係如以上定義之烷基。除非另有指明,否則意指的是其中的R為C1-C8烷基的硫烷基。實例包括甲硫基、乙硫基、丙硫基、1-甲基乙硫基、丁硫基、1-甲基-丙硫基、2-甲基丙硫基、1,1-二甲基乙硫基、戊硫基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基,己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基和1-乙基-2-甲基丙硫基。
如於本說明書中所使用,「鹵基硫烷基」指的是如上文定義 的硫烷基,其中碳原子部分或完全經鹵原子取代。除非另有指明,否則意指的是其中R為C1-C8烷基的鹵基硫烷基。實例包括氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯氟-甲硫基、氯二氟甲硫基、1-氯乙硫基、1-溴乙硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基、五氟乙硫基和1,1,1-三氟丙-2-硫基。
如於本說明書中所使用,「芳基」,以及諸如芳氧基之衍生術語,指的是苯基、二氫茚基或萘基,較佳為苯基。術語雜芳基,以及諸如雜芳氧基之衍生術語,指的是含有一或多個雜原子(即N、O或S)的5元或6元芳香環;這些芳香族與雜芳香環可融合至其他芳香族及/或雜芳香環系統。芳基或雜芳基取代基可以不經取代,或是經一個或多個選自於鹵素、羥基、硝基、氰基、甲醯基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6鹵烷基、C1-C6鹵烷氧基、C1-C6醯基、C1-C6硫烷基、C1-C6烷基亞磺醯基、C1-C6烷基磺醯基、C1-C6烷氧基羰基、C1-C6胺甲醯基、羥基羰基、C1-C6烷基羰基、胺基羰基、C1-C6烷胺基羰基、C1-C6二烷胺基羰基的取代基取代,如果該取代基是立體相容的且滿足化學鍵結與應變能的規則。較佳的取代基包括鹵素、C1-C2烷基和C1-C2鹵烷基。
如於本說明書中所使用,烷基羰基指的是一烷基基團連接在羰基基團上。C1-C3烷基羰基及C1-C3鹵烷羰基指的是在其中有一C1-C3烷基基團連接在羰基基團上(此基團含有總數2到4個碳原子)的基團。
如於本說明書中所使用,烷氧基羰基指的是化學式中 R是烷基的基團。
如於本說明書中所使用,芳烷基指的是經芳基取代之烷基。C7-C10芳烷基指的是在基團中,碳原子總數為7到10個的基團。
如於本說明書中所使用,「烷胺基」指的是經一或二個烷基取代之胺基,取代的烷基彼此可以是相同的或是不同的烷基。
如於本說明書中所使用,「鹵烷胺基」指的是一於其中的烷基碳原子部分或完全經鹵原子取代之烷胺基。
如於本說明書中所使用,「C1-C6烷胺基羰基」指的是化學式RNHC(O)-的基團,其中R為C1-C6烷基,而C1-C6二烷胺基羰基指的是化學式R2NC(O)-的基團,其中每一個R各自獨立為C1-C6烷基。
如於本說明書中所使用,「烷胺甲醯基」指的是在氮原子上經烷基取代之胺甲醯基基團。
如於本說明書中所使用,「烷基磺醯基」指的是在化學式 中R是烷基的基團。
如於本說明書中所使用,「胺甲醯基」(carbamyl,也被稱作 carbamoyl和aminocarbonyl)指的是化學式的基團。
如於本說明書中所使用,「雙烷膦醯基」指的是化學式 的基團,其中R在每次的出現皆獨立地為烷基。
如於本說明書中所使用,「C1-C6三烷基矽基」指的是化學式-SiR3的基團,其中每個R獨立地為C1-C6烷基基團(此基團含有總數3到18個的碳原子)。
如於本說明書中所使用,「Me」指的是甲基基團;「OMe」指的是甲氧基基團;i-Pr指的是異丙基基團。
如於本說明書中所使用,術語「鹵素」,包括諸如鹵基(halo)之衍生術語,指的是氟、氯、溴和碘。
如於本說明書中所使用,「農業上可接受的鹽及酯」,指的是表現出除草活性的鹽及酯,或是可於植物、水或土壤中轉化或能轉化成所述除草劑的鹽及酯。例示性之農業上可接受的酯,其會被,或者可以被水解、氧化、代謝或以其他方式轉化,例如,在植物、水或土壤中被轉化,而形成相應的羧酸,根據pH值該羧酸可處於解離或未解離的型態。
作為示例之用,酯包括了那些從C1-C12烷基、C3-C12烯基、C3-C12炔基或C7-C10經芳基取代之烷基醇,諸如甲基醇、異丙醇、1-丁醇、2-乙基己醇、丁氧基乙醇、甲氧基丙醇、烯丙基醇、炔丙基醇、環己醇,或不經取代或經取代苯甲醇,所衍生出來的酯。苯甲醇可以經1到3個取代基取代,取代基獨立地選自鹵素、C1-C4烷基或C1-C4烷氧基。酯的製備,可以藉由使用任意數量的適宜的活化劑,諸如那些作為胜肽耦合用的活化劑,如環己碳二亞胺(DCC)或羰基二咪唑(CDI),來將酸耦合醇類,以製備酯;在有鹼類的條件之下,諸如在有三乙胺或碳酸鋰的條件之下,可藉由將酸與烷化劑反應,例如與經取代或未經取代的鹵烷類、經取代或未經取代的鹵炔類、經取代或未經取代的氰基鹵烷類(例如氰甲基乙酸酯,諸如氰甲基2-溴乙酸酯)或是經取代或未經取代的烷基磺酸酯)反應來製備酯;藉由將與一酸相應的醯氯和一適當的醇類反應來製備酯;在有酸催化劑的條件下,藉由將一相應的酸與一適當的醇類反應來製備酯,或是以轉酯化的方式製備酯。
式(I)的化合物包括N-氧化物。砒啶N-氧化物可以藉由氧化相應的砒啶來獲得。合適的氧化方法可以在一些文章中找到說明,例如在Houben-Weyl,Methoden der organischen Chemie[Methods in organic chemistry],expanded and subsequent volumes to the 4th edition,volume E 7b,p.565 f.中可見。
此處描述的的化合物為式(I)化合物:
其中X為N或CY,其中Y為氫、鹵素、C1-C3烷基、C1-C3鹵烷基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3烷氧基、C1-C3硫烷基或C1-C3鹵基硫烷基;R1為經CN取代之C3-C12炔基或C1-C3烷基;R2為鹵素、C1-C4烷基、C1-C4鹵烷基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C4烷氧基、C1-C4鹵烷氧基、C1-C4硫烷基、C1-C4鹵基硫烷基、胺基、C1-C4烷胺基、C2-C4鹵烷胺基、甲醯基、C1-C3烷基羰基、C1-C3鹵烷羰基、氰基或式-CR17=CR18-SiR19R20R21的基團,其中R17為氫、F或Cl;R18為氫、F、Cl、C1-C4烷基或C1-C4鹵烷基;且R19、R20及R21獨立地為C1-C10烷基、C3-C6環烷基、苯基、經取代苯基、C1-C10烷氧基或OH;R3及R4獨立地為氫、C1-C6烷基、C1-C6鹵烷基、C3-C6烯基、C3-C6鹵烯基、C3-C6炔基、甲醯基、C1-C3烷基羰基、C1-C3鹵烷羰基、C1-C6烷氧基羰基、C1-C6烷胺甲醯基、C1-C6烷基磺醯基、C1-C6三烷基矽基、C1-C6雙烷膦醯基,或R3和R4與N相連共同為一5元或6元飽和環,或R3和R4共同 代表=CR3' (R4' ),其中R3' 及R4' 獨立地為氫、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷胺基,或R3' 和R4' 與=C相連共同代表一5元或6元飽和環;R5為氫、鹵素、C1-C4烷基、C1-C4鹵烷基、環丙基、鹵基環丙基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3烷硫基、C1-C3鹵基硫烷基、胺基、C1-C4烷胺基、C2-C4鹵烷胺基、OH或CN;R6及R6' 獨立地為氫、鹵素、C1-C4烷基、C1-C4鹵烷基、環丙基、鹵基環丙基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3硫烷基、C1-C3鹵基硫烷基、胺基、C1-C4烷胺基或C2-C4鹵烷胺基、OH、CN或NO2;R7及R7' 獨立地為氫、鹵素、C1-C4烷基、C1-C4鹵烷基、環丙基、鹵基環丙基、C2-C4烯基、C2-C4鹵烯基、C2-C4炔基、C1-C3烷氧基、C1-C3鹵烷氧基、C1-C3硫烷基、C1-C3鹵基硫烷基、胺基、C1-C4烷胺基、C2-C4鹵烷胺基或苯基;R8為氫、C1-C6烷基、C1-C6鹵烷基、C3-C6烯基、C3-C6鹵烯基、C3-C6炔基、甲醯基、C1-C6烷基羰基、C1-C6環烷基羰基、C1-C6鹵烷羰基、C1-C6烷氧基羰基、C1-C6鹵烷氧基羰基、芳羰基、雜芳羰基、C1-C6烷胺甲醯基、C1-C6硫烷基、C1-C6烷基磺醯基、C1-C6鹵烷基磺醯基、芳基磺醯基、C1-C6三烷基矽基、胺基、C1-C4烷胺基、氰基或苯基。
在一些實施例中,式(I)化合物為
其中X為N、CH、CF、CCl或CBr;R1為經CN取代之C3-C12炔基或C1-C3烷基;R2為氯;R3及R4為氫;R5為氫、鹵素、OH、胺基、CN、C1-C3烷基、C1-C3烷氧基、C1-C3烷胺基或環丙基;R6及R6' 獨立地為氫、鹵素、OH、NH2、CN、C1-C3烷基、C1-C3烷氧基、環丙基或乙烯基;R7及R7' 獨立地為氫、鹵素、C1-C3烷基、C1-C3烷氧基、C1-C3硫烷基、環丙基、C1-C3烷胺基或苯基;以及R8為氫、C1-C6烷基羰基、C1-C6環烷基羰基、C1-C6-烷氧基羰基或芳羰基;或其N-氧化物或其農業上可接受的鹽類。
在一些實施例中,式(I)化合物為
其中R2為鹵素、C2-C4-烯基、C2-C4鹵烯基或C1-C4烷氧基;R5為氫或F;R6為氫或F;R6' 為氫;以及R7及R7' 獨立地為氫或鹵素。
在一些實施例中,式(I)化合物為
其中R2為氯、甲氧基、乙烯基或1-丙烯基;R3及R4為氫;以及X為CF。
在一些實施例中:R1為炔丙基;且式(I)化合物為
在一些實施例中:R1為氰基甲基;式(I)化合物為
對其中X為CH或CF且R1為H的4-胺基-6-(雜環)吡啶甲酸,以及在其中X為N且R1為H的6-胺基-2-(雜環)嘧啶羧酸,其合成的流程,在Eckelbarger等人的美國專利號第9,637,505號專利中有描述,於此全文引用併入本說明書中。
對其中的R1、R2、R3、R4、R5、R6、R6’、R7、R7’及R8皆如上文所定義的式(I)化合物,其合成的流程以流程圖1表示
酸1-1可以藉由酯化作用被轉化為式(I)化合物(流程圖1、步驟 a )。酯的製備,可以藉由使用任意數量的適宜的活化劑,諸如那些作為胜肽耦合用的活化劑,如環己碳二亞胺(DCC)或羰基二咪唑(CDI),來將酸耦合醇類以製備酯;在有鹼類,諸如三乙胺或碳酸鉀或鋰的條件之下,可藉由將酸與烷化劑反應,例如與經取代或未經取代的鹵烷類、經取代或未經取代的鹵炔類、經取代或未經取代的氰基鹵炔類,或是經取代或未經取代的烷基磺酸酯反應來製備酯;藉由將與一酸相應的醯氯和一適當的醇類反應來製備酯;或在有一酸催化劑條件下,藉由將一相應的酸與一適當的醇類反應來製備酯。反應可以在極性、非質子的溶劑中進行,例如二甲基亞碸、N,N-二甲基甲醯胺、二氯甲烷或1,2-二氯乙烷。
在一些實施例中,本說明書所提供的化合物、組成物以及方法,會與一個或多個其他除草劑結合使用,以控制更多種類的非所欲的植被。當與一個或多個其他除草劑結合使用時,本說明書中所提供的化合物可以與其他的除草劑或與多個除草劑組成配方、在藥桶中混合其他的除草劑或與多個除草劑,或是和其他的除草劑或與多個除草劑依序地施用。可以和本說明書揭露的化合物結合運用的一些除草劑包括但不限於4-CPA;4-CPB;4-CPP;2,4-D;2,4-D膽鹼鹽、2,4-D酯類及胺類;2,4-DB; 3,4-DA;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、三氟羧草醚、苯草醚、丙烯醛、拉草(alachlor)、草毒死(allidochlor)、禾草滅(alloxydim)、烯丙醇、阿洛克(alorac)、安默屈迪(ametridione)、莠滅淨(ametryn)、安米布嗪(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、殺草強(amitrole)、胺基磺酸銨、莎稗磷(anilofos)、安尼速隆(anisuron)、黃草靈(asulam)、阿特拉通(atraton)、莠去津(atrazine)、唑啶草酮、四唑嘧磺隆、疊氮津(aziprotryne)、燕麥靈(barban)、BCPC、氟丁醯草胺、草除靈(benazolin)、苯卡巴松(bencarbazone)、氟草胺、呋草磺、苄嘧磺隆(bensulfuron-methyl)、地散磷(bensulide)、殺草丹(benthiocarb)、苯達松鈉(bentazon-sodium)、胺酸殺(benzadox)、雙苯嘧草酮、苄草胺、苯雙噻隆(benzobicyclon)、吡草酮(benzofenap)、氟草黃(benzofluor)、苯甲醯丙胺酸、苯噻隆(benzthiazuron)、雙環比隆(bicyclopyrone)、甲羧除草醚(bifenox)、雙丙胺膦、雙草醚鈉、硼砂、除草定(bromacil)、溴波尼(bromobonil)、溴丁醯草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴莠敏(brompyrazon)、丁基拉草(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、布賽達唑(buthidazole)、丁噻隆(buthiuron)、雙丁樂靈(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、蘇達滅(butylate)、二甲胂酸(cacodylic acid)、苯酮唑、氯酸鈣、氰胺鈣、凱本達克(cambendichlor)、卡巴蘇蘭(carbasulam)、卡草胺(carbetamide)、卡波賽唑(carboxazole)、唑酮草酯(carfentrazone-ethyl)、CDEA、CEPC、甲氧除草醚(chlomethoxyfen)、草滅平(chloramben)、地快樂(chloranocryl)、氯拉寄普(chlorazifop)、可樂津(chlorazine)、氯溴隆(chlorbromuron)、氯炔靈(chlorbufam)、氟萊特隆 (chloreturon)、伐草克(chlorfenac)、燕麥酯(chlorfenprop)、氟咪殺(chlorflurazole)、氯甲丹(chlorflurenol)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、草枯醚(chlornitrofen)、三氯丙酸、綠麥隆(chlorotoluron)、氯草隆(chloroxuron)、羥敵草腈(chloroxynil)、克洛普卡(chlorprocarb)、氯苯胺靈(chlorpropham)、氯磺隆(chlorsulfuron)、敵草索(chlorthal)、草克樂(chlorthiamid)、吲哚酮草酯(cinidon-ethyl)、環庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、咯草隆(cisanilide)、氯酰草膦(clacyfos)、克草同(clethodim)、一氯吡啶酯、炔草酯(clodinafop-propargyl)、氯伏草(clofop)、異惡草酮(clomazone)、克普草(Clomeprop)、調果酸(cloprop)、氯丙氧定(cloproxydim)、克草立特(clopyralid)、氯酯磺草胺(cloransulam-methyl)、CMA、硫酸銅、CPMF、CPPC、達草醚(credazine)、甲酚、苄草隆(cumyluron)、氰草淨(cyanatryn)、氰草津(cyanazine)、環草特(cycloate)、環吡瑞諾(cyclopyranil)、環吡瑞莫(cyclopyrimorate)、環丙嘧磺隆(cyclosulfamuron)、環殺草(cycloxydim)、環莠隆(cycluron)、氰氟草酯(cyhalofop-butyl)、牧草快(cyperquat)、環丙津(cyprazine)、三環噻草胺(cyprazole)、環草胺(cypromid)、香草隆(daimuron)、茅草枯(dalapon)、邁隆(dazomet)、異丁草胺(delachlor)、甜菜安(desmedipham)、敵草淨(desmetryn)、燕麥敵(di-allate)、麥草畏(dicamba)、敵草腈(dichlobenil)、氯雙脲(dichloralurea)、苄胺靈(dichlormate)、滴丙酸(dichlorprop)、滴丙酸-P(dichlorprop-P)、氯甲草(diclofop)、雙氯磺草胺(diclosulam)、迭森快(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)、二氟吡隆(diflufenzopyr)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、排草淨(dimethametryn)、二甲酚草胺(dimethenamid)、精二甲酚草胺(dimethenamid-P)、草滅散(dimexano)、地 米達腙(dimidazon)、敵樂胺(dinitramine)、迪樂芬諾(dinofenate)、硝丙酚(dinoprop)、戊硝酚(dinosam)、特樂酚(dinoseb)、特樂酯(dinoterb)、雙苯醯草胺(diphenamid)、異丙淨(dipropetryn)、敵草快(diquat)、滴硫鈉(disul)、氟硫草定(dithiopyr)、敵草隆(diuron)、DMPA、DNOC、DSMA、EBEP、乙甘三嗪(eglinazine)、草哆嗦(endothal)、艾丙諾斯(epronaz)、EPTC、抑草蓬(erbon)、戊草丹(esprocarb)、乙丁烯氟靈(ethalfluralin)、埃斯苯紮邁(ethbenzamide)、胺苯磺隆(ethametsulfuron)、磺噻隆(ethidimuron)、抑草威(ethiolate)、埃瑟苯紮米(ethobenzamid)、埃托苯紮米(etobenzamid)、乙呋草磺(ethofumesate)、氯氟草醚(ethoxyfen)、乙氧嘧磺隆(ethoxysulfuron)、硝草酚(etinofen)、艾尼丙密(etnipromid)、乙氧苯草胺(etobenzanid)、EXD、菲那蘇蘭(fenasulam)、涕丙酸(fenoprop)、噁唑禾草靈(fenoxaprop)、精噁唑禾草靈(fenoxaprop-P-ethyl)、精噁唑禾草靈+雙苯噁唑酸(isoxadifen-ethyl)、芬奧薩碸(fenoxasulfone)、芬昆諾三酮(fenquinotrione)、芬特拉科(fenteracol)、噻唑禾草靈(fenthiaprop)、四唑醯草胺(fentrazamide)、非草隆(fenuron)、硫酸亞鐵(ferrous sulfate)、麥草伏(flamprop)、高效麥草伏(flamprop-M)、啶嘧磺隆(flazasulfuron)、雙氟磺草胺(florasulam)氯氟吡啶酯(Florpyrauxifen-Benzyl)、伏寄普(fluazifop)、吡氟禾草靈(fluazifop-P-butyl)、異丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟芬尼康(flufenican)、氟噠嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟默嗪(flumezin)、氟胺草酯(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、伏草隆(fluometuron)、消草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、氟硫隆(fluothiuron)、氟胺草唑(flupoxam)、氟丙鉑秀(flupropacil)、四氟丙酸 (flupropanate)、氟啶嘧磺隆(flupyrsulfuron)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、呋草酮(flurtamone)、氟噻乙草酯(fluthiacet)、氟磺胺草醚(fomesafen)、甲醯嘧磺隆(foramsulfuron)、殺木膦(fosamine)、呋氧草醚(furyloxyfen)、草銨膦(glufosinate)、固殺草(glufosinate-ammonium)、草甘膦(glyphosate)、鹵索芬(halosafen)、合速隆(halosulfuron-methyl)、氟啶草(haloxydine)、吡氟氯禾靈(haloxyfop-methyl)、精吡氟氯禾靈(haloxyfop-P-methyl)、哈勞克西芬甲酯(halauxifen-methyl)、六氯丙酮(hexachloroacetone)、六氟鹽(hexaflurate)、環嗪酮(hexazinone)、咪草酯(imazamethabenz)、甲氧咪草菸(imazamox)、甲咪唑菸酸(imazapic)、滅草菸(imazapyr)、滅草喹(imazaquin)、咪草菸(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、碘保諾(iodobonil)、碘甲烷(iodomethane)、碘磺隆(iodosulfuron)、碘磺隆(iodosulfuron)、碘苯腈(ioxynil)、依哌嗪(ipazine)、三唑苯胺(ipfencarbazone)、伊普利密旦(iprymidam)、丁脒醯胺(isocarbamid)、異丙淨(isocil)、丁嗪草酮(isomethiozin)、異草完隆(isonoruron)、異丙靈(isopolinate)、異樂靈(isopropalin)、異丙隆(isoproturon)、異噁隆(isouron)、異噁草胺(isoxaben)、異噁氯妥(isoxachlortole)、異噁唑草酮(isoxaflutole)、異噁草醚(isoxapyrifop)、卡草靈(karbutilate)、酮螺氧(ketospiradox)、乳氟禾草靈(lactofen)、藍三酮(lancotrione)、環草定(lenacil)、利穀隆(linuron)、MAA、MAMA、MCPA酯類和胺類、MCPA-乙硫基、MCPB、2-甲-4-氯丙酸(mecoprop)、高2-甲-4-氯丙酸(mecoprop-P)、甲基特樂酯(medinoterb)、苯噻草胺(mefenacet)、麥夫迪(mefluidide)、普拉嗪(mesoprazine)、甲磺胺磺隆(mesosulfuron)、甲基磺草酮(mesotrione)、威百畝(metam)、噁唑醯草胺(metamifop)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、嗪吡嘧磺隆 (metazosulfuron)、美氟拉隆(metflurazon)、甲基苯噻隆(methabenzthiazuron)、美索丙鉑林(methalpropalin)、滅草唑(methazole)、甲硫苯卡(methiobencarb)、麥瑟唑林(methiozolin)、美速隆(methiuron)、醚草通(methometon)、美保嗪(methoprotryne)、溴甲烷、異硫氰酸甲酯、甲基殺草隆(methyldymron)、甲氧苯草隆(metobenzuron)、溴穀隆(metobromuron)、異丙甲草胺(metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、賽克津(metribuzin)、甲磺隆(metsulfuron)、草達滅(molinate)、殺草利(monalide)、莫尼索隆(monisouron)、一氯乙酸(monochloroacetic acid、綠穀隆(monolinuron)、滅草隆(monuron)、伐草快(morfamquat)、MSMA、萘丙胺(naproanilide)、萘氧丙草胺(napropamide)、、萘氧丙草胺-M(napropamide-M)、萘草胺(naptalam)、草不隆(neburon)、菸嘧磺隆(nicosulfuron)、尼平拉芬(nipyraclofen)、滅殺草(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、氟草敏(norflurazon)、草完隆(noruron)、OCH、坪草丹(orbencarb)、鄰二氯苯(ortho-dichlorobenzene)、嘧苯胺磺隆(orthosulfamuron)、安磺靈(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、草噠松(oxapyrazon)、環氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、吡草醚(paraflufen-ethyl)、對氟隆(parafluron)、百草枯(paraquat)、克草敵(pebulate)、壬酸(pelargonic acid)、二甲戊樂靈(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorophenol)、蔬草滅(pentanochlor)、環戊噁草酮(pentoxazone)、黃草伏(perfluidone)、烯草胺(pethoxamid)、棉胺寧(phenisopham)、甜菜寧(phenmedipham)、乙基甜菜寧(phenmedipham-ethyl)、醯草隆(phenobenzuron)、醋酸苯汞(phenylmercury acetate)、胺氯吡啶酸(picloram)、氟吡草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、亞砷酸 鉀(potassium arsenite)、疊氮鉀(potassium azide)、氰酸鉀(potassium cyanate)、丙草胺(pretilachlor)、甲基氟嘧磺隆(primisulfuron-methyl)、丙噻嗪(procyazine)、苯胺靈(prodiamine)、氟唑草胺(profluazol)、環丙氟靈(profluralin)、苯草酮(profoxydim)、甘撲津(proglinazine)、調環酸鈣(prohexadione-calcium)、撲滅通(prometon)、撲草淨(prometryn)、毒草安(propachlor)、敵稗(propanil)、普拔草(propaquizafop)、撲滅津(propazine)、苯胺靈(propham)、異丙草胺(propisochlor)、丙氧磺隆(propoxycarbazone)、嗪咪唑嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、甲硫磺樂靈(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、撲滅生(proxan)、丙炔草胺(prynachlor)、皮丹能(pydanon)、雙唑草腈(pyraclonil)、吡草醚乙酯(pyraflufen-ethyl)、磺醯草吡唑(pyrasulfotole)、雙唑草腈(pyrazogyl)、比拉唑諾(pyrazolynate)、乙基吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、嘧啶肟草醚(pyribenzoxim)、稗草畏(pyributicarb)、氯草定(pyriclor)、吡啶達醇(pyridafol)、噠草特(pyridate)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧啶硫蕃(pyrimisulfan)、嘧硫草醚甲基(pyrithiobac-methyl)、派羅克殺草碸(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、滅藻醌(quinoclamine)、氯藻胺(quinonamid)、快伏草(quizalofop)、精喹禾靈(quizalofop-P-ethyl)、硫氰苯胺(rhodethanil)、碸嘧磺隆(rimsulfuron)、索氟納西(saflufenacil)、高效異丙甲草胺(S-metolachlor)、塞布拉嗪(sebuthylazine)、密草通(secbumeton)、西殺草(sethoxydim)、環草隆(siduron)、西瑪津(simazine)、西默通(simeton)、西草淨(simetryn)、SMA、亞砷酸鈉(sodium arsenite)、疊氮化鈉(sodium azide)、氯酸鈉(sodium chlorate)、磺草酮(sulcotrione)、菜草畏(sulfallate)、甲磺草胺(sulfentrazone)、甲嘧磺隆 (sulfometuron)、草硫膦(sulfosate)、磺醯磺隆(sulfosulfuron)、硫酸(sulfuric acid)、蘇格力卡品(sulglycapin)、滅草靈(swep)、TCA、胺草磷(tebutam)、丁噻隆(tebuthiuron)、特福三酮(tefuryltrione)、環磺酮(tembotrione)、得殺草(tepraloxydim)、特草定(terbacil)、芽根靈(terbucarb)、特丁草胺(terbuchlor)、甲氧去草淨(terbumeton)、特丁津(terbuthylazine)、去草淨(terbutryn)、四氟隆(tetrafluron)、甲氧噻草胺(thenylchlor)、噻氟隆(thiazafluron)、噻草啶(thiazopyr)、噻達茲明(thidiazimin)、噻苯隆(thidiazuron)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、禾草丹(thiobencarb)、替芬昔(tiafenacil)、仲草丹(tiocarbazil)、賽克林(tioclorim)、硝黃草酮(tolpyralate)、苯吡唑草酮(topramezone)、苯草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野麥畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、殺草畏(tricamba)、綠草定酯類和胺類、滅草環(tridiphane)、草達津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟草嗪(trifludimoxazin)、氟樂靈(trifluralin)、氟胺磺隆(triflusulfuron)、三氟丙酸(trifop)、三氟禾草肟(trifopsime)、三羥基三嗪(trihydroxytriazine)、三甲隆(trimeturon)、三丙丹(tripropindan)、草達克(tritac)、三氟甲磺隆(tritosulfuron)、滅草猛(vernolate)和二甲苯草胺(xylachlor)。搭配混合的對象可以被配成游離酸或鹼,或是配成如上文所定義的鹽或酯類。
本說明書中所述的化合物及組成物可一般地與習知的除草劑安全劑結合運用,諸如解草酮(benoxacor)、殺草丹(benthiocarb)、芸苔素內酯(brassinolide)、解草酯類(cloquintocet)(如解毒喹(cloquintocet-mexyl))、解草胺腈(cyometrinil)、香草隆(daimuron)、二氯丙烯胺(dichlormid)、迪賽隆(dicyclonon)、哌草丹(dimepiperate)、二硫松(disulfoton)、解草唑(fenchlorazole-ethyl)、解草啶(fenclorim)、解草安(flurazole)、肟草安 (fluxofenim)、呋喃解草唑(furilazole)、髮夾蛋白質(harpin proteins)、雙苯噁唑酸(isoxadifen-ethyl)、吡唑解草酯(mefenpyr-diethyl)、2-雙氯甲基-2-甲基-1,3-二氧戊環,也被稱作MG 191、二氯乙醯-1-氧-4-含氮螺旋(4,5)-癸烷,也被稱作MON 4660、萘二甲酸酐(naphthalic anhydride;NA)、解草腈(oxabetrinil)、(R,S)-3-二氯乙醯-2,2,5-三甲基唑烷,也被稱作R-29148、美克麥芬(metcamifen)、N-苯基磺醯基苯甲酸胺類或其之混合物,以增加其之選擇性。
在一些實施例中,本說明書提供的化合物係可使用在含有一除草有效量之所述化合物以及至少一農業上可接受之佐劑或載體的混合物之中。例示性的佐劑或載體係包括那些對經濟作物沒有毒性,或是沒有顯著毒性的佐劑或載體,例如在有作物存在的時候,要施用組成物以作選擇性雜草控制時,其使用的濃度沒有毒性,或是沒有顯著毒性,及/或不會和說明書中的化合物或其他組成物的成分起化學反應,或是顯著地起化學反應。此種混合物可以設計成在施用時直接用在雜草上,或是用在其所在地,或是以濃縮劑或配方的方式,在施用前與其他的載體和佐劑稀釋使用。其可為固態,舉例而言諸如粉劑、粒劑、水分散性粒劑或是可溼性粉劑,或是可為液態,諸如(例如)乳化濃縮劑、溶液、乳劑或懸浮液。其也可以用預拌的方式,或是需另在藥桶中攪拌的方式提供。
對於所屬技術領域的專業人員來說,適合的農用佐劑與載體是習知的技術。這些佐劑包含但不限於作物油濃縮物(礦物油(85%)+乳化劑(15%));壬基酚乙氧基化物;苯甲基椰油烷基二甲基四級銨鹽;石油烴、烷酯、有機酸及陰離子界面活性劑之摻合物;C9-C11烷基多醣苷磷酸化醇乙氧基化物;天然一級醇(C12-C16)乙氧基化物;二-第二-丁基酚EO-PO嵌段共聚物;聚矽氧烷-甲基帽;壬基酚乙氧基化物+尿素硝銨(urea ammonium nitrate);乳化甲基化籽油;十三醇(合成)乙氧基化物(8EO);牛脂胺乙氧基化物(15 EO);PEG(400)二油酸酯-99。
可使用的液態載體包括水和有機溶劑。作為示例用的有機溶劑包括但不限於石油餾分或烴類,諸如礦物油、芳族溶劑、石蠟油及其類似物;植物油,例如大豆油、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、桐油及其類似物;以上植物油之酯類;一元醇或二元醇、三元醇或其他低級多元醇(含有4-6個羥基)之酯類,諸如2-乙基己酯硬脂酸、n-丁基油酸酯、肉豆蔻酸異丙酯、丙二醇二油酸酯、丁二酸二辛酯、己二酸二丁酯、鄰苯二甲酸二辛酯及其類似物;單羧酸、二羧酸及聚羧酸之酯類及其類似物。特定有機溶劑包括甲苯、二甲苯、石油腦、作物油、丙酮、甲基乙基酮、環己酮、三氯乙烯、四氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇單甲醚及二乙二醇單甲醚、甲醇、乙醇、異丙醇、戊醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯啶酮、N,N-二甲基烷基醯胺、二甲亞碸、液體肥料及其類似物。在一些實施例中,水是用於濃縮劑稀釋物的載體。
適合的固態載體包括滑石粉、葉蠟石土(pyrophyllite clay)、矽土(silica)、美國白土(attapulgus clay)、高嶺土、矽藻土(kieselguhr)、白堊(chalk)、矽藻土(diatomaceous earth)、石灰(lime)、碳酸鈣、皂土、漂白土(Fuller's earth)、棉籽殼、小麥粉、大豆粉、浮石粉、木粉、核桃殼粉、木質素及其類似物。適合的固態載體也可包括前述固態載體的結合物。
在一些實施例中,於本說明書揭露的組成物內會使用到一個或多個界面活性劑(surface active agents)。在一些實施例中,固態和液態的組成物都會用到此種界面活性劑,例如那些被設計成需要在施用前以載體稀釋的組成物。界面活性劑可以具陰離子性或是陽離子性,且可以被用 以當作乳化劑、潤濕劑、懸浮劑或其他的功能來使用。於配方調製時的傳統上會用上表面活性劑(surfactants),且同時可以用於本案配方的表面活性劑已有被記載,尤其是有被記載於McCutcheon’s Detergents and Emulsifiers Annual,MC Publishing Corp.,Ridgewood,New Jersey,1998,and in Encyclopedia of Surfactants,Vol.I-III,Chemical Publishing Co.,New York,1980-81之中。常見的界面活性劑包括烷基硫酸酯之鹽,如月桂基硫酸二乙醇銨;烷基芳基磺酸鹽類,如十二烷基苯磺酸鈣;烷基酚-環氧烷加成產物,壬基酚-C18乙氧基化物;醇烯化氧加成產物,如十三醇-C16乙氧基化物;肥皂類,如硬脂酸鈉;烷基萘-磺酸鹽,如二丁基萘磺酸鈉;磺基丁二酸鹽之二烷酯,如二(2-乙基己基)磺基丁二酸鈉;山梨糖醇酯,如山梨糖醇油酸酯;四級胺,如氯化月桂基三甲基銨;脂肪酸之聚乙二醇酯,如聚乙二醇硬脂酸酯;環氧乙烷與環氧丙烷之嵌段共聚物;單及二烷基磷酸酯之鹽;植物油或籽油,如大豆油、菜籽油/芥花油、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、桐油及其類似物;以及以上植物油之酯,例如甲酯。
很多時候其中的一些材料如植物油及其酯類,能夠彼此互相替代地作為農用佐劑、液態載體或作為界面活性劑使用。
其他常用於農業用組成物中的佐劑包括增容劑、消泡劑、螯合劑、中和劑及緩衝劑、腐蝕抑制劑、染料、氣味劑、展佈劑、滲透助劑、黏著劑、分散劑、增稠劑、冰點降低劑、抗微生物劑及其類似物。組成物亦可含有其他相容組分,例如其他除草劑、植物生長調節劑、殺真菌劑、殺昆蟲劑及其類似物,且可與液態肥料或固態、微粒的肥料載劑,諸如硝酸銨、尿素及其類似物一起配製。
本說明書揭露之除草組成物中的活性成分濃度通常為約 0.001至約98重量%。通常會使用的濃度是約0.01至約90重量%。對於被設計成以濃縮劑方式使用的組成物,其中的活性成分濃度通常是從約5至約98重量百分比,較佳的為約10至約90重量百分比。這種組成物在施用以前,一般會以惰性的載體稀釋,諸如水。通常施用在雜草上,或是施用在雜草所在地之上的已稀釋組成物,會含有約0.0001至約1重量百分比的活性成分,較佳的是含有約0.001至約0.05重量百分比。
如於本說明書中使用,作為連接一數量詞的修飾語"約",涵蓋了所說明的數值,且具有上下文所指的含義(例如其至少包含了因為測量該特定數量,所導致的誤差程度)當上下文是在說明一個範圍時,使用的修飾語"約",應被視為揭露了兩個端點的絕對值所定義出的範圍。例如,「從約2至約4」的範圍,也揭露了「從2至4」的範圍。
本案組成物可藉由使用傳統的地面或空中撒粉器、噴霧器以及撒粒器、藉由添加至灌溉水或水稻田面水,以及藉由所屬技術領域的專業人員習知的其他傳統方式,施用於雜草上或其所在地。
在一些實施例中,本案所說明的化合物與組成物,是用於萌後施用、萌前施用、對稻米的水田或是對水體作水中施用(例如池塘、湖泊與溪流),或是作為除盡(burn-down)施用。
在一些實施例中,本案提供的化合物和組成物適用於控制長在作物之間的雜草,包括但不限於柑橘、蘋果、橡膠樹、棕梠油樹、林地、直接播種(direct-seeded)、湛水直播(water-seeded)以及移植的稻米、小麥、大麥、燕麥、黑麥、高粱、玉米(corn/maize)、牧草地(pastures)、草場(grasslands)、牧場(rangelands)、休耕地(fallowland)、草皮、木本果園及藤本 果園、水生作物或行栽作物,以及非作物的環境例如工業用植被管理或公用路線穿越用地。在一些實施例中,化合物和組成物是用來控制木本植物、闊葉與禾草類雜草或莎草科植物(sedges)。
在一些實施例中,本說明書提供的化合物和組成物是用來控制稻米中非所欲的植被。在某些特定的實施例中,非所欲的植被為寬葉臂形草(Brachiaria platyphylla)(Groseb.)Nash(闊葉信號草,BRAPP)、指草(Digitaria sanguinalis)(L.)Scop.(大型馬唐草,DIGSA)、稗(Echinochloa crus-galli)(L.)P.Beauv.(稗草(barnyardgrass),ECHCG)、芒稷(Echinochloa colonum)(L.)LINK(芒稷(junglerice),ECHCO)、水田稗(Ard.)Fritsch(早稗(early watergrass),ECHOR)、水稗(Echinochloa oryzicola)(Vasinger)Vasinger(晚稗(late watergras),ECHPH)、田間鴨嘴草(Ischaemum rugosum)Salisb.(鴨嘴草(saramollagrass),ISCRU),千金子(Leptochloa chinensis)(L.)Nees(中國千金子(Chinese sprangletop),LEFCH)、馬唐(Leptochloa fascicularis)(Lam.)Gray(有芒千金子(bearded sprangletop),LEFFA)、多花千金子(Leptochloa panicoides)(Presl.)Hitchc.(亞馬遜千金子(Amazn sprangletop),LEFPA)、洋野黍(Panicum dichotomiflorum)(L.)Michx.(秋黍(fall panicum),PANDI)、毛花雀稗Poir.(百喜草(dallisgrass),PASDI),異花莎草(Cyperus difformis)L.(小花水莎草(smallflower flatsedge),CYPDI)、黃土香(Cyperus esculentus)L.(黃莎草(yellow nutsedge),CYPES)、碎米莎草(Cyperus iria)L.(米莎草(rice flatsedge),CYPIR)、香附子(Cyperus rotundus)L.(紫香附(purple nutsedge),CYPRO)、荸薺屬(Eleocharis)種(ELOSS),四稜飄拂草(Fimbristylis miliacea)(L.)Vahl(水風草(globe fringerush),FIMMI)、螢藺(Schoenoplectus juncoides)Roxb.(日本藨草(Japanese bulrush),SPCJU)、多穗藨草(Schoenoplectus maritimus)L.(海濱莞草,SCPMA)、水毛花(Schoenoplectus mucronatus)L.(稻 田藨草(ricefield bulrush),SCPMU)、合萌屬(Aeschynomene)種、(合萌(jointvetch),AESSS)、空心蓮子草(Alternanthera philoxeroides)(Mart.)Griseb.(長梗滿天星(Alligator weed),ALRPH)、澤瀉(Alisma plantago-aquatica)L.(常見水車前草,ALSPA)、莧屬(Amaranthus)種,(豬草(pigweeds)與莧菜(amaranths),AMASS)、長葉水莧菜(Ammannia coccinea)Rottb.(水莧菜(redstem),AMMCO)、鱧腸(Eclipta alba)(L.)Hassk.(美國偽雛菊(American false daisy),ECLAL)、沼生異蕊花(Heteranthera limosa)(SW.)Willd./Vahl(水生萵苣(ducksalad),HETLI)、腎型異蕊花(Heteranthera reniformis)R.& P.(圓葉異蕊花(roundleaf mudplantain),HETRE)、碗仔花(Ipomoea hederacea)(L.)Jacq.(常春藤葉牽牛花(ivyleaf morningglory),IPOHE)、美洲母草(Lindernia dubia)(L.)Pennell(矮假繁縷(low false pimpernel),LIDDU),雨久花(Monochoria korsakowii) Regel & Maack(鴨舌草(monochoria),MOOKA)、鴨舌草(Monochoria vaginalis)(Burm.F.)C.Presl ex Kuhth,(鴨舌草(monochoria),MOOVA)、裸花水竹葉(Murdannia nudiflora)(L.)Brenan(鴿草,MUDNU)、賓州蓼(Polygonum pensylvanicum)L.,(賓夕維尼亞蕁麻(Pennsylvania smartweed),POLPY)、春蓼(Polygonum persicaria)L.(火炭母草(ladysthumb),POLPE)、辣椒蓼(Polygonum hydropiperoides)Michx.(POLHP,軟蓼(mild smartweed))、印度節節菜(Rotala indica)(Willd.)Koehne(印度紅骨仔草(Indian toothcup),ROTIN)、慈姑屬種(三角草(arrowhead),SAGSS)、大果田菁(Sesbania exaltata)(Raf.)Cory/Rydb.Ex Hill(大麻田菁(hemp sesbania),SEBEX),或尖瓣花(Sphenoclea zeylanica)Gaertn.(鵝草(gooseweed),SPDZE)。
在一些實施例中,本案提供的化合物與組成物是用來控制穀物間非所欲的植被。在某些特定的實施例中,非所欲的植被為大穗看麥 娘(Alopecurus myosuroides)Huds.(黑草(blackgrass),ALOMY)、阿披拉草(Apera spica-venti)(L.)Beauv.(風草(windgrass),APESV)、野燕麥(Avena fatua)L.(野生燕麥(wild oat),AVEFA)、絹雀麥(Bromus tectorum)L.(旱雀麥(downy brome),BROTE)、多花黑麥草(Lolium multiflorum)Lam.(義大利黑麥草(Italian ryegrass),LOLMU)、細鷸草(Phalaris minor)Retz.(小加那利草(littleseed canarygrass),PHAMI)、早熟禾|(Poa annua)L.(一年生藍草(annual bluegrass),POAAN)、金色狗尾草(Setaria pumila)(Poir.)Roemer & J.A.Schultes(黃色狐尾草(yellow foxtail),SETLU)、狗尾草(Setaria viridis)(L.)Beauv.(綠色狐尾草(green foxtail),SETVI)、絲路薊(Cirsium arvense)(L.)Scop.(加拿大薊(Canada thistle),CIRAR)、八仙草(Galium aparine)L.(小鋸藤(catchweed bedstraw),GALAP)、地膚(Kochia scoparia)(L.)Schrad.(地膚(kochia),KCHSC)、圓齒野芝麻(Lamium purpureum)L.(紫色寶蓋草(purple deadnettle),LAMPU)、春黃菊(Matricaria recutita)L.(野生洋甘菊(wild chamomile),MATCH)、同花母菊(Matricaria matricarioides)(Less.)Porter(鳳梨草(pineappleweed),MATMT)、虞美人(Papaver rhoeas)L.(虞美人(common poppy),PAPRH)、卷莖蓼(Polygonum convolvulus)L.(野生蕎麥(wild buckwheat),POLCO)、刺沙蓬(Salsola tragus)L.(俄羅斯蓟(Russian thistle),SASKR)、繁縷(Stellaria media)(L.)Vill.(鵝腸草(common chickweed),STEME)、阿拉伯婆婆納(Veronica persica)Poir.(波斯婆婆納(Persian speedwell),VERPE)、野生堇菜(Viola arvensis)Murr.(田野紫蘿蘭(field violet),VIOAR)或三色堇(Viola tricolor)L.(野生紫蘿蘭(wild violet),VIOTR)。
在一些實施例中,本案所提供的化合物及組成物是用來控制牧場和牧草地中非所欲的植被。在某些特定的實施例中,非所欲的植被為豬草(Ambrosia artemisiifolia)L.(常見豚草(common ragweed),AMBEL)、 決明(Cassia obtusifolia)(鐮刀豆(sickle pod),CASOB)、矢車菊(Centaurea maculosa)auct.non Lam.(斑點矢車菊(spotted knapweed),CENMA)、絲路薊(Cirsium arvense)(L.)Scop.(加拿大薊,CIRAR)、田旋花(Convolvulus arvensis)L.(田野旋花(field bindweed),CONAR)、乳漿大戟(Euphorbia esula)L.(多葉大戟(leafy spurge),EPHES)、刺萵苣(Lactuca serriola)L./Torn.(刺萵苣(prickly lettuce),LACSE)、長葉車前草(Plantago lanceolata)L.(鹿角車前草(buckhorn plantain),PLALA)、大羊蹄(Rumex obtusifolius)L.(闊葉酸模(broadleaf dock),RUMOB)、刺金午時花(Sida spinosa)L.(刺金午時花(prickly sida),SIDSP)、野田芥(Sinapis arvensis)L.(野生芥菜(wild mustard),SINAR)、苦苣菜(Sonchus arvensis)L.(多年生苦苣菜(perennial sowthistle),SONAR)、一枝黃花屬(Solidago)種(秋麒麟草(goldenrod),SOOSS)、西洋蒲公英(Taraxacum officinale)G.H.Weber ex Wiggers(蒲公英(dandelion)、TAROF),菽草(Trifolium repens)L.(白三葉草(white clover),TRFRE)或異株蕁麻(Urtica dioica)L.(常見蕁麻(common nettle),URTDI)。
在一些實施例中,本案所提供的化合物及組成物是用來控制行栽作物間非所欲的植被。在某些特定的實施例中,非所欲的植被為大穗看麥娘(Alopecurus myosuroides)Huds.(黑草(blackgrass),ALOMY)、野燕麥(Avena fatua)L.(野生燕麥(wild oat),AVEFA)、寬葉臂形草(Brachiaria platyphylla)(Groseb.)Nash(闊葉信號草(broadleaf signalgrass),BRAPP)、指草(Digitaria sanguinalis)(L.)Scop.(大型馬唐草,DIGSA)、稗(Echinochloa crus-galli)(L.)P.Beauv.(稗草(barnyardgrass),ECHCG)、芒稷(Echinochloa colonum)(L.)Link(芒稷(junglerice),ECHCO)、多花黑麥草(Lolium multiflorum)Lam.(義大利黑麥草(Italian ryegrass),LOLMU)、洋野黍(Panicum dichotomiflorum)Michx.(秋黍(fall panicum),PANDI)、稷(Panicum miliaceum)L.(野生小米(wild-proso millet),PANMI)、法氏狗尾草(Setaria faberi)Herrm.(巨型狐尾草(giant foxtail),SETFA)、狗尾草(Setaria viridis)(L.)Beauv.(綠色狐尾草(green foxtail),SETVI)、詹森草(Sorghum halepense)(L.)Pers.(詹森草(Johnsongrass),SORHA)、蜀黍(Sorghum bicolor)(L.)Moench ssp.葦狀高粱(Arundinaceum)(蜀黍(shattercane),SORVU)、黃土香(Cyperus esculentus)L.(黃莎草(yellow nutsedge),CYPES)、香附子(Cyperus rotundus)L.(紫香附(purple nutsedge),CYPRO)、莔麻(Abutilon theophrasti)Medik.(絨葉草(velvetleaf),ABUTH)、莧屬種(豬草(pigweeds)與莧菜(amaranths),AMASS)、豬草(Ambrosia artemisiifolia)L.(常見豚草(common ragweed),AMBEL)、裸穗豬草(Ambrosia psilostachya)DC.(西方豚草(western ragweed),AMBPS)、三裂葉豬草(Ambrosia trifida)L.(巨型豚草(giant ragweed),AMBTR)、敘利亞馬利筋(Asclepias syriaca)L.(常見乳草(common milkweed),ASCSY)、藜(Chenopodium album)L.(常見藜(common lambsquarters),CHEAL)、絲路薊(Cirsium arvense)(L.)Scop.(加拿大薊(Canada thistle),CIRAR)、圓葉鴨跖草(Commelina benghalensis)L.(熱帶紫露草(tropical spiderwort),COMBE)、番曼陀蘿(Datura stramonium)L.(吉姆森草(jimsonweed),DATST)、胡蘿蔔(Daucus carota)L.(野生胡蘿蔔(wild carrot),DAUCA)、白苞猩猩草(Euphorbia heterophylla)L.(野生猩猩木(wild poinsettia),EPHHL)、野茼蒿(Erigeron bonariensis)L.(多毛飛蓬(hairy fleabane),ERIBO)、光莖飛蓬(Erigeron canadensis)L.(加拿大飛蓬(Canadian fleabane),ERICA)、向日葵(Helianthus annuus)L.(常見太陽花(common sunflower),HELAN)、長梗毛娥房藤(Jacquemontia tamnifolia)(L.)Griseb.(小花牽牛花(smallflower morningglory),IAQTA)、碗仔花(Ipomoea hederacea)(L.)Jacq.(常春藤葉牽牛花(ivyleaf morningglory),IPOHE)、白星薯(Ipomoea lacunosa)L.(白色牽牛花(white morningglory),IPOLA)、刺萵苣(Lactuca serriola)L./Torn.(刺萵苣(prickly lettuce),LACSE)、馬齒莧(Portulaca oleracea)L.(常見馬齒莧(common purslane),POROL)、刺金午時花(Sida spinosa)L.(刺金午時花(prickly sida),SIDSP)、野田芥(Sinapis arvensis)L.(野生芥菜(wild mustard),SINAR)、龍葵(Solanum ptychanthum)Dunal(東方黑龍葵(eastern black nightshade),SOLPT)或蒼耳(Xanthium strumarium)L.(常見蒼耳(common cocklebur),XANST)。
在一些實施例中,施用比率是約1至約4,000克/公頃(g/ha),於萌後操作使用。在一些實施例中,施用比率是約1至約4,000(g/ha),於萌前操作使用。
本案所述的化合物、組成物以及方法,用在可耐5-烯醇丙酮醯莽草酸-3-磷酸(EPSP)合成酶抑制劑(例如可耐嘉磷塞)、可耐榖胺醯胺合成酶抑制劑(例如可耐草銨膦)、可耐合成生長素(例如、可耐麥草畏(dicamba)、可耐苯氧類生長素、可耐吡啶氧基生長素)、可耐生長素傳輸抑制劑、可耐乙醯輔酶A羧酶(ACC酶)抑制劑(例如可耐芳氧苯氧丙酸酯)、可耐乙醯乳酸合成酶(ALS)或乙醯醇酸合成酶(AHAS)抑制劑(例如可耐二氮雜戊烯類、可耐磺醯尿素、可耐嘧啶基硫代苯甲酸酯、可耐三唑嘧啶類、可耐磺醯基胺基羰基三唑啉酮)、可耐4-羥苯基-丙酮酸二氧酶(HPPD)抑制劑、可耐原紫質原氧化酶(PPO)抑制劑、可耐光合系統(PS)II抑制劑(例如可耐三嗪類及可耐溴苯腈)的作物上時(例如(但不限於)大豆、棉花、芥花/油菜籽、稻米、穀物、玉米、草皮等等),可以與EPSP合成酶抑制劑(例如嘉磷塞)、榖胺醯胺合成酶抑制劑(例如固殺草(glufosinate))、合成生長素(例如麥草畏(dicamba)、苯氧類生長素、吡啶氧基生長素)、ACC酶抑制劑(例如芳氧苯氧丙酸酯)、ALS抑制劑(例如二氮雜戊烯類、磺醯尿素、嘧啶基硫 代苯甲酸酯、三唑嘧啶類以及磺醯基胺基羰基三唑啉酮)、HPPD抑制劑、PPO抑制劑以及PS II抑制劑(例如三嗪類及溴苯腈)一起施用。可以將組成物和方法,用在擁有複數種性狀或多種性狀堆疊,以賦予多種化學物質及/或多種作動機制的抑制劑之耐性的作物之間,來控制非所欲的植被。
本案提供的化合物與組成物也可以運用在控制對除草劑有抗性或耐性的雜草上。作為示例用的具抗性或耐性的雜草,包括但不限於,可抗或可耐ALS(或AHAS)抑制劑、PS II抑制劑、ACC酶抑制劑、合成生長素、PS I抑制劑、EPSP合成酶抑制劑、微管組裝抑制劑、脂類合成抑制劑、PPO抑制劑、類胡蘿蔔素生物合成抑制劑、極長鏈脂肪酸(VLCFA)抑制劑、八氫番茄紅素去飽和酶(PDS)抑制劑、榖胺醯胺合成酶抑制劑、HPPD抑制劑、有絲分裂抑制劑、纖維素生物合成抑制劑、具有多種作動機制的除草劑,諸如二氯喹啉酸(quinclorac),以及未分類的除草劑,諸如芳胺基丙酸、野燕枯(difenzoquat)、草藻滅(Endothall)以及有機砷的生物型。作為示例用的具抗性或耐性的雜草,包括但不限於,可抗或可耐多種除草劑、多種化學藥品種類、以及多種除草劑作動機制的生物型。
所述的實施例以及以下的實例是出於說明性的目的,並不意欲限制申請專利範圍之範疇。本文中所述組成物的其他相關調整、使用或是結合,在不出本案所主張的主體之精神與範圍下,對於所屬技術領域中具有通常知識者將是顯而易見的。
標題化合物的製備流程是根據文獻Das,A.,et al.Org.Lett. 2017,19,5794-5797,,其以引用方式全體併入本文。
標題化合物是根據美國專利申請公開號第2014/0274695號的中的前驅物實例3、製備流程50來製備。
標題化合物可如美國專利申請公開號第2014/0274695號中的實例1中所述內容來製備。或者也可以根據以下方式製備。
在一具磁力攪拌、冷凝裝置、內部溫度探棒以及氮氣環境下的3公升(L)三頸的長頸瓶中加入甲基4-胺基-3,6-二氯-5-氟基吡啶甲酸酯(製程參照Fields et al.,Tetrahedron Letters 2010,51,79-81;75克(g),314 毫莫耳(mmol))以及7-氟-6-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)-1-(三異丙基矽基)-1H-吲哚(175g,377mmol)。依序加入乙腈(CH3CN;1255毫升(mL))與2莫耳濃度(M)的磷酸鉀溶液(314mL,628mmol)。該混合物係接著經排氣(evacuated)並以氮氣(3x)回填,再加入雙-(三苯基膦)二氯化鈀(11.12g,15.69mmol)。抽空長頸瓶並回填(3x),將混合物在65℃下加熱。3小時(h)之後,加入氟化鉀(74.4g,1255mmol),再繼續加熱16h。將反應混合物冷卻至室溫,以Celite過濾。將各相分離,在減壓的條件下移除溶劑。將殘留物與己烷研磨碎,經過濾及用己烷沖洗以收集固態物。獲得的固態物以二氯甲烷(CH2Cl2)處理、過濾、用小量的CH2Cl2淋洗,並在50℃下真空抽乾。分離出一呈灰白色固體的標題化合物(73.5g,69%)。
標題化合物可以如美國專利申請公開號第2014/0274695號中的實例12製備,或是以如下方式製備。
將甲基4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸酯(288毫克(mg),0.853mmol)溶解於四氫呋喃(THF;2.0mL)、甲醇(CH3OH;2.0mL)與水(1.0mL)之中。加入氫氧化鋰水合物(100mg,2.383mmol)。將該反應混合物置於室溫下攪拌過夜。濃縮乾燥該反應混合物。獲得的固態物以水稀釋,使懸浮液為酸性(pH~3).將懸浮液以乙酸乙酯(EtOAc,3x)萃取。結合的有機萃取物以飽和的氯化鈉(NaCl)水溶液沖洗、於硫酸鎂上乾燥 (MgSO4)、過濾並濃縮。分離出一呈灰白色固體的標題化合物(256mg,93%)。
將混合了4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸(1.5g,4.63mmol)、碳酸鉀(0.833g,6.02mmol)與3-溴丙炔(0.549mL,5.10mmol)於N,N-二甲基甲醯胺(DMF;18.5mL)之中的混合物,在室溫下攪拌4小時。將反應混合物倒進半飽和的碳酸氫鈉(NaHCO3)水溶液中,並以EtOAc(2x)萃取。結合的有機萃取物置於MgSO4上乾燥、過濾和濃縮。藉由自動化快速管柱層析系統純化殘留物(矽膠,己烷/EtOAc梯度)。將獲得的油態物加入極少量的CH2Cl2以開啟結晶化。使用音波震盪幫助進一步的結晶化。隨後加入己烷以進一步地沉澱產物。將固態物過濾、用己烷(2x)沖洗並真空乾燥。分離出一呈白色固體的標題化合物(1.33g,79%):熔點140-142℃;1H NMR(400MHz,CDCl3)δ 8.49(s,1H),7.49(dd,J=8.3,0.7Hz,1H),7.32-7.27(m,2H),6.61(td,J=3.3,2.1Hz,1H),4.97(d,J=2.5Hz,2H),4.91(s,2H),2.53(t,J=2.5Hz,1H);19F NMR(376MHz,CDCl3)δ -135.47,-135.55,-137.23,-137.32;ESIMS m/z 362([M+H]+)。
以下的化合物依實例5的方式合成。
分離出一呈白色固體的標題化合物(730mg,65%):熔點139-140℃;1H NMR(300MHz,DMSO-d 6)11.83(s,1H),7.52(d,J=3.1Hz,1H),7.47(d,J=8.2Hz,1H),7.13-7.03(m,3H),6.59(t,J=3.2Hz,1H),5.29(s,2H);ESIMS m/z 363([M+H]+)。
使用表面面積為103.2平方公分(cm2)的塑膠盆,將所欲測試的植物品種之種子種在Sun Gro MetroMix® 306種植用混合物(planting mixture)之中,其一般含有一6.0至6.8的pH值以及約30%的有機質含量。當需要確保有良好的發芽以及健康的植物時,會進行殺真菌的處理及/或其他化學或物理上的處理。讓植物於溫室中生長7-36天(d),維持大約14小時(h)光照周期,其中白日時溫度為18℃,夜晚時為17℃。定期給予營養與水分,如有需要則以1000瓦由頂上給予的(overhead)金屬鹵化物燈提供補充光源。當植物長到第2或第3真葉齡(true leaf stage)時,便用在測試之上。
將配製的化合物5其一等份式樣(100公克酸當量/每公升(g ae/L);乳劑(EC))、化合物6(100g ae/L;EC)或化合物7(100g ae/L;EC)放置在一25mL玻璃瓶中並在體積比1.25%(體積百分比(v/v))的Actirob B乳化菜籽油水溶液體積中稀釋,以獲得一儲備液。濃縮的儲備液以1.25% v/v的Actirob B乳化菜籽油水溶液之水性混合物作稀釋,以提供一合適的施用比率。化合物的需求是基於每公頃187公升(L/ha)的比例下要有12mL的施 用體積來決定。配製的化合物是以一個頂上(overhead)施予的Mandel履帶式噴灑器施用在0.503平方公尺(m2)施用區域中的植物材料上,其裝有一8002E噴嘴,被調校至187L/ha的刻度,噴灑高度是高於平均植物頂冠的18英呎(43公分(cm))。用相同的方法對控制組的植物噴灑空白溶劑。
經處理的植物以及控制組的植物如上述是被放置在一溫室中,以地下灌溉的方式給水,避免測試的化合物被洗掉。經過20-22天後,以目測判定的方式,判斷測試的植物狀況,用來與控制組植物的狀況之間作比較,且以0-100%的量尺方式計分,其中0代表無傷害,100代表完全死亡。以目測判定的方式作判斷,比較測試的植物狀況與控制組植物的狀況,且以0-100%的量尺方式計分,其中0代表無傷害,100代表完全死亡。
在表格中所顯示的間隔時間裡,以目測評估方式評估雜草控制(外觀檢測百分比(%))。所回報的數值是平均值。表格中有相同的字母接在後方的平均值,代表沒有顯著差異(P=0.5,鄧肯氏多變域測驗(Duncan’s New MRT))。資料整理如表1所示。
田野測試是在加拿大進行(於Ellerslie,Alberta;Nisku,Alberta以及Hanley,Saskatchewan),以評估化合物5、6、7的有效性。測試為隨機完全區集的設計,作四重複。測試是在具天然雜草族群的春小麥田中進行,土地面積為寬2-3公尺(m)、長8-10m(寬度 x 長度)。作物的種植是使用一般農作方式施肥、播種以及照顧以確保作物可良好的生長。
所有給予除草劑的處理,都是在萌後對處於BBCH(植物物候發展階段)14至22生長階段的作物施用。除草劑是以後背式或單車式噴霧器施用,以二氧化碳(CO2)作噴射劑。噴霧器使用扁平扇形進氣噴霧噴嘴, 校準到提供一致的噴灑模式,以使用100L/ha的噴灑容積對葉子提供全面的覆蓋。所有給藥的處理都是用1.25% v/v的甲基化籽油(MSO)施用。對雜草的植物毒性評估,是在施用後的幾個間隔期間以目測檢查整體控制的百分比,與未處理的控制組土地作比較。通常來說,每個給藥的處理都是作四重複來評估。所有給藥的處理結果都是四重複的平均值。
將化合物5、化合物6及化合物7各自以乳劑(EC)配方,以100g ae/L EC比例施用。
結果以表2到表4顯示。
田野測試是在西班牙(Banares與Granon)及德國(Bielefeld)進行,以評估化合物5、化合物6和化合物7的有效性。該試驗為隨機完全阻斷設計,作三到四重複。測試是在具天然雜草族群的冬小麥田中進行,土地面積為寬2-2.5公尺(m)、長6-8m(寬度 x 長度)。作物的種植是使用一般農作方式施肥、播種以及照顧以確保作物可良好的生長。
所有給予除草劑的處理,都是在萌後對處於BBCH 21至23生長階段的作物施用。除草劑是以後背式或單車式噴霧器施用,以空氣作為噴射劑。噴霧器使用扁平扇形進氣噴霧噴嘴,校準到提供一致的噴灑模式,以使用200L/ha的噴灑容積對葉子提供全面的覆蓋。所有給藥的處理都是用1.25% v/v的甲基化籽油(MSO)施用。對雜草的植物毒性評估,是在施用後的幾個間隔期間以目測檢查整體控制的百分比,與未處理的控制組土地作比較。通常來說,每個給藥的處理會是作三到四重複來評估。所有給藥的處理結果都是三或四重複的平均值。
化合物5、化合物6及化合物7各自以乳劑(EC)配方,以100g ae/L EC比例施用。
結果以表5到表8顯示。
在表1至表8中用了以下的縮寫:
化合物5=丙-2-炔-1-基4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸酯
化合物6=氰甲基4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸酯
化合物7=苯甲基4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸酯
ANTAR=田春黃菊(Anthemis arvensis)(田野洋甘菊(field chamomile))
CENCY=矢車菊(Centaurea cyanus)(玉米花(cornflower))
CHEAL=藜(Chenopodium album)L.(常見藜(common lambsquarters))
CIRAR=絲路薊(Cirsium arvense)(L.)Scop.(加拿大薊)
FUMOF=球果紫菫(Fumaria officinalis)(common fumitory(常見延胡索))
KCHSC=地膚(Kochia scoparia)(L.)Schrad.(地膚(kochia))
MATCH=春黃菊(Matricaria recutita)L.(野生洋甘菊(wild chamomile))
MATIN=母菊(Matricaria inodora)(無香小白菊(scentless mayweed))
PAPRH=虞美人(Papaver rhoeas)L.(虞美人(common poppy))
Res-PAPRH=虞美人(Papaver rhoeas)L.(虞美人(common poppy)),其可抗苯磺隆(tribenuron)及噻吩磺隆(thifensulfuron)(ALS-乙醯乳酸合成酶的作動機制)及2,4-D。
POLCO=卷莖蓼(Polygonum convolvulus)L.(野生蕎麥(wild buckwheat))
SINAR=野田芥(Sinapis arvensis)L.(野生芥菜(wild mustard))
STEME=繁縷(Stellaria media)(L.)Vill.(鵝腸草(common chickweed))
VERHE=睫毛婆婆納(Veronica hederifolia)(常春藤葉婆婆納(ivyleaved speedwell))
VERSS=婆婆納屬(Veronica)種(婆婆納(speedwell))
g ae/ha=每公頃克酸當量(grams acid equivalent per hectare)
LSD=最小顯著性差異(least significant difference)
DAAA=施用A之後的天數
表1:在溫室環境下給予除草化合物後的關鍵雜草的目視防治百分比(%)
從前述的結果中可見,本案式(I)的化合物具有除草活性。從前述的結果中可見,化合物5及化合物6展現出比化合物7更優異的除草活性。這些新型的化學除草劑,提供了更廣泛的雜草控制、對雜草有更高的活性,以及提供了一種可以管理對傳統上控制雜草的除草劑產生出抗性的雜草的解決方式。
雖在描述的揭露內容中有示例性的部分或實例,本案的揭露內容可以在不出本案精神與範疇之下有進一步的修改。因此,使用本案揭露內容其一般性原則所作出的任何的變化、使用或改編,為本申請意欲涵蓋的範圍。此外,從本案揭露內容為出發點的內容配合與本案揭露內容有相關的所屬技術領域中習知或慣常的操作實務,共同為本申請意欲涵蓋的範圍。
益處、優勢、問題解法,以及任何可引發出益處、優勢或者是產生出解法,或是讓解法更為明顯之元件(element),都不構成本案關鍵、必須或是基本的特徵或元件。因此,能夠限制本案範圍者,只有所附上的申請專利範圍,其中在提及一元件時,使用單數的詞語說明,並不是意欲表達"一個且只有一個",而是在說明"一個或多個",除非另外有明示。另外,在申請專利範圍中使用類似“至少一A、B或C’”的用語,是意欲被解讀為代表在一實施例中可單獨有A、一實施例中可單獨有B、一實施例中可單獨有C,或是在一個單一的實施例中有元件A、B或C的任意結合;例如A與B、A與C、B與C或A與B與C。
在本說明書的詳細實施方式中,提及"一個實施例"、"一實施例"、"一示例性的實施例"等等,代表的是所說明的實施例可能包括一特別的特徵、結構或特性,但不是每個實施例都必需要包括該特別的特徵、結構或特性。另外,此種用語所指的不一定是同一個實施例。更甚者,當 在說明與一實施例有關的一個特別的特徵、結構或是特性時,應該理解本案所揭露內容,對於在其他實施例中的該特徵、結構或特性所能夠貢獻的益處,都是在所屬技術領域中專業人士的知識範圍內,不論有無特別明示。
Claims (28)
- 一種式(I)化合物:
- 如申請專利範圍第1項所述之化合物,其中X為N、CH、CF、CCl或CBr;R 1為經CN取代之C 3-C 12炔基或C 1-C 3烷基;R 2為氯; R 3及R 4為氫;R 5為氫、鹵素、OH、胺基、CN、C 1-C 3烷基、C 1-C 3烷氧基、C 1-C 3烷胺基或環丙基;R 6及R 6′獨立地為氫、鹵素、OH、NH 2、CN、C 1-C 3烷基、C 1-C 3烷氧基、環丙基或乙烯基;R 7及R 7′獨立地為氫、鹵素、C 1-C 3烷基、C 1-C 3烷氧基、C 1-C 3硫烷基、環丙基、C 1-C 3烷胺基或苯基;以及R 8為氫、C 1-C 3烷基、苯基或C 1-C 3烷基羰基;或其N-氧化物或其農業上可接受的鹽類。
- 如申請專利範圍第1項所述之化合物,其中X為CH、CF或N;R 1為經CN取代之C 3-C 12炔基或C 1-C 3烷基;R 2為鹵素、C 1-C 4烷基、C 1-C 4鹵烷基、C 2-C 4烯基、C 2-C 4鹵烯基、C 2-C 4炔基、C 1-C 4-烷氧基、C 1-C 4鹵烷氧基、C 1-C 4硫烷基或C 1-C 4鹵基硫烷基;R 3及R 4為氫、C 1-C 6烷基、C 1-C 6鹵烷基、C 3-C 6烯基、C 3-C 6鹵烯基、C 3-C 6炔基、甲醯基、C 1-C 3烷基羰基、C 1-C 3鹵烷羰基,或R 3和R 4共同代表=CR 3′(R 4′),其中R 3′和R 4′獨立地為氫、C 1-C 6烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 6烷氧基或C 1-C 6烷胺基;R 5為氫、鹵素、C 1-C 4烷基、C 1-C 4鹵烷基、C 2-C 4烯基、C 2-C 4鹵烯基、C 2-C 4炔基、C 1-C 3烷氧基、C 1-C 3鹵烷氧基、C 1-C 3硫烷基、C 1-C 3鹵基硫烷基、胺基、C 1-C 4烷胺基或C 2-C 4鹵烷胺基; R 6及R 6′獨立地為氫、鹵素、C 1-C 4烷基、C 1-C 4鹵烷基、環丙基、鹵基環丙基、C 2-C 4烯基、C 2-C 4鹵烯基、C 2-C 4炔基、C 1-C 3烷氧基、C 1-C 3鹵烷氧基、CN或NO 2;R 7及R 7′獨立地為氫、鹵素、C 1-C 4烷基、C 1-C 4鹵烷基、C 1-C 3烷氧基、C 1-C 3鹵烷氧基、C 1-C 3硫烷基、環丙基、胺基或C 1-C 4烷胺基;R 8為氫、C 1-C 6烷基、C 1-C 6鹵烷基、C 3-C 6烯基、C 3-C 6鹵烯基、C 3-C 6炔基、甲醯基、C 1-C 6烷基羰基、C 1-C 6環烷基羰基、C 1-C 6鹵烷羰基、C 1-C 6烷氧基羰基、C 1-C 6鹵烷氧基羰基、芳羰基、雜芳羰基、C 1-C 6烷胺甲醯基、C 1-C 6硫烷基、C 1-C 6烷基磺醯基、C 1-C 6鹵烷基磺醯基、芳基磺醯基、C 1-C 6三烷基矽基、胺基、C 1-C 4烷胺基、氰基或苯基。
- 如申請專利範圍第3項所述之化合物,其中:R 2為鹵素、C 2-C 4烯基、C 2-C 4鹵烯基或C 1-C 4烷氧基。
- 如申請專利範圍第4項所述之化合物,其中R 2為Cl、甲氧基、乙烯基或1-丙烯基。
- 如申請專利範圍第3項所述之化合物,其中R 3及R 4為氫。
- 如申請專利範圍第3項所述之化合物,其中R 5為氫或F。
- 如申請專利範圍第7項所述之化合物,其中R 5為F。
- 如申請專利範圍第3項所述之化合物,其中R 6為氫或F。
- 如申請專利範圍第3項所述之化合物,其中R 6和R 6′為氫。
- 如申請專利範圍第3項所述之化合物,其中R 6′為氫。
- 如申請專利範圍第3項所述之化合物,其中:R 2為鹵素、C 2-C 4-烯基、C 2-C 4鹵烯基或C 1-C 4烷氧基;R 5為氫或F;R 6為氫或F; R 6′為氫;以及R 7及R 7′獨立地為氫或鹵素。
- 如申請專利範圍第12項所述之化合物,其中R 2為氯、甲氧基、乙烯基或1-丙烯基。
- 如申請專利範圍第12項所述之化合物,其中R 3及R 4為氫。
- 如申請專利範圍第13項所述之化合物,其中R 3和R 4為氫。
- 如申請專利範圍第12項所述之化合物,其中X為CF。
- 如申請專利範圍第13項所述之化合物,其中X為CF。
- 如申請專利範圍第14項所述之化合物,其中X為CF。
- 如申請專利範圍第15項所述之化合物,其中X為CF。
- 如申請專利範圍第3項所述之化合物,其中:R 2為氯、甲氧基、乙烯基或1-丙烯基;以及R 3和R 4為氫。
- 如申請專利範圍第3項所述之化合物,其中:R 2為氯、甲氧基、乙烯基或1-丙烯基;R 3及R 4為氫;以及X為CF。
- 如申請專利範圍第21項所述之化合物,其中該化合物為丙-2-炔-1-基4-胺基-3-氯-5-氟-6-(7-氟-1 H-吲哚-6-基)吡啶甲酸酯。
- 如申請專利範圍第21項所述之化合物,其中該化合物為氰基甲基4-胺基-3-氯-5-氟-6-(7-氟-1 H-吲哚-6-基)吡啶甲酸酯。
- 一種除草組成物,其包含如申請專利範圍第1項所述之化合物以及一農業上可接受的佐劑或載體。
- 如申請專利範圍第24項所述之組成物,其進一步包含至少一額外的除草化合物。
- 如申請專利範圍第24項所述之組成物,其進一步包含一安全劑。
- 一種控制非所欲的植物之方法,包含:提供如申請專利範圍第1項所述之化合物;以及將該化合物施用在一非所欲的植物或其所在地之上。
- 一種控制非所欲的植物之方法,包含:提供如申請專利範圍第25項所述之組成物;以及將該組成物施用在一非所欲的植物或其所在地之上。
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CN113226036A (zh) * | 2018-11-07 | 2021-08-06 | 科迪华农业科技有限责任公司 | 包含羧酸吡啶除草剂和微管组装抑制剂除草剂的组合物 |
CA3118687A1 (en) * | 2018-11-07 | 2020-05-14 | Corteva Agriscience Llc | Compositions comprising pyridine carboxylate herbicides and 4-hydroxyphenyl-pyruvate dioxygenase (hppd) inhibitor herbicides |
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