CN111065269B - 4-氨基-6-(杂环)吡啶甲酸酯和6-氨基-2-(杂环)嘧啶-4-羧酸酯及其作为除草剂的用途 - Google Patents
4-氨基-6-(杂环)吡啶甲酸酯和6-氨基-2-(杂环)嘧啶-4-羧酸酯及其作为除草剂的用途 Download PDFInfo
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- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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Classifications
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- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
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- 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
- C07D401/02—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 containing two hetero rings
- C07D401/10—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 containing two hetero rings linked by a carbon chain containing aromatic rings
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- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
4‑氨基‑6‑(杂环)吡啶甲酸酯及其衍生物;6‑氨基‑2‑(杂环)嘧啶‑4‑羧酸酯及其衍生物;以及使用它们作为除草剂的方法。
Description
相关申请的交叉引用
本申请要求2017年5月10日提交的美国临时专利申请序列号62/504,148的权益,其全部公开内容据此以引用方式明确并入。
技术领域
本公开包括除草剂化合物、包含所述除草剂化合物的组合物,以及用此类化合物和组合物控制不期望植被的方法。
背景技术
不期望植被(例如杂草)的出现是农民在作物、牧地和其他环境中面临的一个长期问题。杂草与作物竞争并且对作物产量产生负面影响。化学除草剂的使用是控制不期望植被的重要工具。在作物田(例如,小麦、大麦、玉米、燕麦、芥菜和甜菜)、牧地、路边、荒地和沟埂中,不期望植被地肤(kochia)和普通罂粟(common poppy)的问题特别突出。
例如,地肤(Kochia scoparia)是一种常见于美国西部和加拿大的早发夏季一年生物种。它是草本双子叶植物并且是藜科成员。地肤作为观赏植物从欧洲传入北美,因为它在夏末和秋季呈红色。地肤(Kochia scoparia(L.)Schrad.)是整个北部大平原(NGP)的作物田、牧地、路边、荒地和沟埂中最麻烦的一年生阔叶杂草之一。如果不及早控制,地肤会导致包括小麦、大麦、玉米和甜菜在内的作物严重减产(最多至60%),并且可能是化学休耕地(chem-fallow)中的主要问题杂草。
种子几乎没有休眠,并且在免耕条件下,位于土壤表面或附近的大部分(>90%)种子在早春发芽,且在整个夏天出现2至3次出苗潮(emergence flush)。夏末,地肤生长迅速并开花。杂草能够自花授粉和异花授粉,并通过种子繁殖。单个地肤植株能够产生最多至50,000颗种子,这些种子可以通过风、水、干草中的污染物、农业设备、或通过农用车辆传播。在成熟期,植株在茎的基部断裂并随盛行风在整个园地中“翻滚”,这是种子散布的独特而快速的机制。此外,地肤很好地适应干旱、盐、炎热和寒冷的条件。
用于尝试控制地肤的除草剂包括乙酰乳酸合酶(ALS)抑制性除草剂、氟草烟(fluroxypyr)、麦草畏(dicamba)和草甘膦。氟草烟和麦草畏是选择性除草剂,其可控制阔叶杂草且通常不伤害禾本种植物。通常应用于地肤控制的(2-二氯苯氧基)乙酸(2,4-D)是无效的。
草甘膦(如孟山都技术有限责任公司(Monsanto Technology LLC),特拉华州有限责任公司(Delaware Limited Liability Company)的注册商标,或其他类似的仿制药)是用于杂草控制的非选择性广谱除草剂。然而,对于在化学休耕地中在种植之前燃尽杂草控制以及对于Roundup(也是孟山都技术有限责任公司的注册商标)作物中的作物内施用,与使用草甘膦超过十年相关的各种因素已导致包括地肤在内的草甘膦抗性杂草(在美国目前有24个物种)的进化。例如,对三嗪、生长素、ALS除草剂和草甘膦具有抗性的地肤生物型已有良好的文档记录。
角罂粟(corn poppy)或普通罂粟(虞美人(Papaver rhoeas))是具有地中海气候的欧洲南部地区的冬季谷物中问题最大的双子叶杂草之一。角罂粟是因其降低谷物产量的能力而为人熟知的竞争性杂草。该物种入侵、生长和在谷物田中持续存在的能力可以归因于永久种子库的形成、延长的发芽期和高种子产量。由于罂粟的抗除草剂生物型的传播,罂粟的管理已成为欧洲谷物种植者和当局的一个严峻且日益严峻的挑战。对磺酰脲类除草剂或/和生长素类除草剂具有抗性的虞美人的群体在比利时、丹麦、法国、德国、希腊、意大利、西班牙、瑞典和英国已有报道。已经在波兰发现了对光合系统II(PSII)抑制性除草剂具有抗性的虞美人的一些群体。虞美人的抗除草剂生物型的传播对谷物生产系统的收益性构成威胁。
因此,仍然需要新的化学除草剂,其提供更广谱的杂草控制、选择性、最小的作物损害、储存稳定性、易处理性、更高的抗杂草活性、和/或解决相对于常规除草剂发展的除草剂耐受性的手段。
发明内容
本文提供了式(I)的化合物:
其中
X为N或CY,其中Y为氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷氧基、C1-C3烷硫基、或C1-C3卤代烷硫基;
R1为被CN取代的C3-C12炔基或C1-C3烷基;
R2为卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、氰基、或式-CR17═CR18-SiR19R20R21的基团,其中R17为氢、F、或Cl;R18为氢、F、Cl、C1-C4烷基、或C1-C4卤代烷基;并且R19、R20和R21独立地为C1-C10烷基、C3-C6环烷基、苯基、经取代的苯基、C1-C10烷氧基、或OH;
R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨甲酰基、C1-C6烷基磺酰基、C1-C6三烷基甲硅烷基、C1-C6二烷基膦酰基、或R3和R4与N合在一起为5元或6元饱和环,或R3和R4合在一起表示=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基,或R3′和R4′与=C合在一起表示5元或6元饱和环;
R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环烷基、卤代环烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、OH或CN;
R6和R6′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基、OH、CN、或NO2;
R7和R7′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、或苯基;
R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C6烷基羰基、C1-C6环烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷氧基羰基、芳基羰基、杂芳基羰基、C1-C6烷基氨甲酰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、芳基磺酰基、C1-C6三烷基甲硅烷基、氨基、C1-C4烷基氨基、氰基、或苯基、或其N-氧化物。
还提供了控制不期望植被的方法,包括提供式(I)的化合物以及(a)使不期望植被或与不期望植被相邻的区域接触,或(b)在苗前使土壤或水接触除草有效量的至少一种式(I)的化合物或其农业上可接受的衍生物。
具体实施方式
I.定义
如本文所用,除草剂和除草活性成分可理解为包括当以适当的量施用时控制不期望植被的化合物。
如本文所用,不期望植被的控制或控制不期望植被是指杀死该植被或预防该植被,或导致对植被的一些其他的负面调节作用,例如与自然生长或发育的偏差、调控、脱水、延迟等。
如本文所用,除草有效量或植被控制量可理解为包括除草活性成分的施用控制相关的不期望植被时的量。
如本文所用,施用除草剂或除草剂组合物可理解为包括将其直接递送至目标植被,或其所在地,或希望控制不期望植被的区域。示例性的施用方法包括但不限于在苗前接触土壤或水,在苗后接触不期望植被或与不期望植被相邻的区域。
如本文中所用,植物和植被可包括但不限于休眠种子、发芽种子、发芽幼苗、从无性繁殖体发芽的植物、不成熟的植被和长成的植被。
如本文所用,不成熟的植被可理解为包括在生殖期之前的小型营养植物,而成熟植被意指生殖期间与之后的营养植物。
如本文所用,除非另有说明,否则酰基是指甲酰基、C1-C3烷基羰基和C1-C3卤代烷基羰基。C1-C6酰基是指甲酰基、C1-C5烷基羰基和C1-C5卤代烷基羰基(该基团含有总共1至6个碳原子)。
如本文所用,烷基是指饱和的直链或支链饱和烃部分。除非另有说明,否则意指C1-C10烷基基团。实例包括甲基、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。
如本文所用,卤代烷基是指直链或支链烷基基团,其中在这些基团中,氢原子可部分或全部被卤素原子取代。除非另有说明,否则意指C1-C8基团。实例包括氯甲基、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。
如本文所用,烯基是指含有双键的不饱和、直链、或支链的烃部分。除非另有说明,否则意指C2-C8烯基。烯基基团可含有多于一个不饱和键。实例包括乙烯基、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。乙烯基是指具有结构–CH=CH2的基团;1-丙烯基是指具有结构–CH=CH-CH3的基团;并且2-丙烯基是指具有结构–CH2-CH=CH2的基团。
如本文所用,炔基代表含有三键的直链或支链烃部分。除非另有说明,否则意指C2-C8炔基基团。炔基基团可含有多于一个不饱和键。实例包括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。
如本文所用,烷氧基是指式R-O-的基团,其中R是如上文所定义的烷基。除非另有说明,否则意指其中R为C1-C8烷基基团的烷氧基基团。实例包括甲氧基、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。
如本文所用,卤代烷氧基是指式R-O-的基团,其中R是如上文所定义的卤代烷基。除非另有说明,否则意指其中R为C1-C8烷基基团的卤代烷氧基基团。实例包括氯甲氧基、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。
如本文所用,烷硫基是指式R-S-的基团,其中R是如上文所定义的烷基。除非另有说明,否则意指其中R为C1-C8烷基基团的烷硫基基团。实例包括甲硫基、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。
如本文所用,卤代烷硫基是指如上文所定义的烷硫基基团,其中碳原子部分或全部被卤素原子取代。除非另有说明,否则意指其中R为C1-C8烷基基团的卤代烷硫基基团。实例包括氯甲硫基、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。
如本文所用,芳基以及如芳氧基的衍生物是指苯基、茚满基或萘基基团,其中苯基是优选的。术语杂芳基以及衍生术语如杂芳氧基是指含有一个或多个杂原子即N、O或S的5元或6元芳环;这些芳环和杂芳环可稠合至其他芳族和/或杂芳族体系。芳基或杂芳基取代基可以是未经取代的或被一个或多个取代基取代,所述取代基选自卤素、羟基、硝基、氰基、甲酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6酰基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷氧基羰基、C1-C6氨基甲酰基、羟基羰基、C1-C6烷基羰基、氨基羰基、C1-C6烷基氨基羰基、C1-C6二烷基氨基羰基,前提条件是取代基是空间相容的,并且满足化学键合和应变能的规则。优选的取代基包括卤素、C1-C2烷基和C1-C2卤代烷基。
如本文所用,烷基羰基是指与羰基基团键合的烷基基团。C1-C3烷基羰基和C1-C3卤代烷基羰基是指其中C1-C3烷基基团键合至羰基基团的基团(所述基团含有总共2至4个碳原子)。
如本文所用,芳基烷基是指被芳基基团取代的烷基基团。C7-C10芳基烷基是指其中基团中的碳原子总数为7至10的基团。
如本文所用,烷基氨基是指被一个或两个可以相同或不同的烷基基团取代的氨基基团。
如本文所用,卤代烷基氨基是指其中烷基碳原子部分或全部被卤素原子取代的烷基氨基基团。
如本文所用,C1-C6烷基氨基羰基是指式RNHC(O)-的基团,其中R为C1-C6烷基,并且C1-C6二烷基氨基羰基是指式R2NC(O)-的基团,其中每个R独立地为C1-C6烷基。
如本文所用,烷基氨甲酰基是指在氮上被烷基基团取代的氨甲酰基基团。
如本文所用,C1-C6三烷基甲硅烷基是指式-SiR3的基团,其中每个R独立地为C1-C6烷基基团(所述基团含有总共3至18个碳原子)。
如本文所用,Me是指甲基基团;OMe是指甲氧基基团;i-Pr是指异丙基基团。
如本文所用,包括衍生术语如卤代基(halo)的术语卤素(halogen)是指氟、氯、溴和碘。
如本文所用,农业上可接受的盐和酯是指表现出除草活性的,或在植物、水或土壤中转化为或可转化为所提及的除草剂的盐和酯。示例性农业上可接受的酯为例如在植物、水或土壤中将或可通过水解、氧化、代谢或其他方式转化成对应的羧酸的那些,取决于pH,羧酸可为解离或非解离形式。
示例性酯包括衍生自下列的那些酯:C1-C12烷基、C3-C12烯基、C3-C12炔基或C7-C10芳基取代的烷基醇,如甲基醇、异丙醇、1-丁醇、2-乙基己醇、丁氧基乙醇、甲氧基丙醇、烯丙醇、炔丙醇、环己醇或未经取代或经取代的苯甲醇。苯甲醇可被1-3个独立地选自卤素、C1-C4烷基或C1-C4烷氧基的取代基取代。酯可通过以下方式制备:使用任意数量的合适活性剂如用于肽偶联的那些(如二环己基碳二亚胺(DCC)或羰基二咪唑(CDI))使酸与醇偶联;在如三乙胺或碳酸锂的碱的存在下使酸与烷化剂反应,所述烷化剂如经取代或未经取代的烷基卤、经取代或未经取代的炔基卤、经取代或未经取代的氰基烷基卤(例如,乙酸氰基甲酯,如2-溴乙酸氰基甲酯)、或经取代或未经取代的烷基磺酸盐;使酸的对应酰基氯与适当的醇反应;在酸催化剂的存在下或通过酯交换反应使对应的酸与适当的醇反应。
式(I)的化合物包括N-氧化物。吡啶N-氧化物可以通过对应吡啶的氧化获得。合适的氧化方法描述于例如Houben-Weyl,Methoden der organischen Chemie[Methods inorganic chemistry],扩展卷和后续卷至第4版,第E 7b卷,第565f页。
II.化合物
本文所述的化合物是式(I)的化合物:
其中
X为N或CY,其中Y为氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷氧基、C1-C3烷硫基、或C1-C3卤代烷硫基;
R1为被CN取代的C3-C12炔基或C1-C3烷基;
R2为卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、氰基、或式-CR17═CR18-SiR19R20R21的基团,其中R17为氢、F、或Cl;R18为氢、F、Cl、C1-C4烷基、或C1-C4卤代烷基;并且R19、R20和R21独立地为C1-C10烷基、C3-C6环烷基、苯基、经取代的苯基、C1-C10烷氧基、或OH;
R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨甲酰基、C1-C6烷基磺酰基、C1-C6三烷基甲硅烷基、C1-C6二烷基膦酰基、或R3和R4与N合在一起为5元或6元饱和环,或R3和R4合在一起表示=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基,或R3′和R4′与=C合在一起表示5元或6元饱和环;
R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、OH或CN;
R6和R6′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基、OH、CN、或NO2;
R7和R7′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、或苯基;
R8为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C6烷基羰基、C1-C6环烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷氧基羰基、芳基羰基、杂芳基羰基、C1-C6烷基氨甲酰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、芳基磺酰基、C1-C6三烷基甲硅烷基、氨基、C1-C4烷基氨基、氰基、或苯基;
在一些实施方案中,式(I)的化合物为
其中
X为N、CH、CF、CCl或CBr;
R1为被CN取代的C3-C12炔基或C1-C3烷基;
R2为氯;
R3和R4为氢;
R5为氢、卤素、OH、氨基、CN、C1-C3烷基、C1-C3烷氧基、C1-C3烷基氨基、或环丙基;
R6和R6′独立地为氢、卤素、OH、NH2、CN、C1-C3烷基、C1-C3烷氧基、环丙基、或乙烯基;
R7和R7′独立地为氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3烷硫基、环丙基、C1-C3烷基氨基、或苯基;并且
R8为氢、C1-C6烷基羰基、C1-C6环烷基羰基、C1-C6-烷氧基羰基、或芳基羰基;
或其N-氧化物或农业上可接受的盐。
在一些实施方案中,式(I)的化合物为
其中
R2为卤素、C2-C4-烯基、C2-C4卤代烯基、或C1-C4烷氧基;
R5为氢或F;
R6为氢或F;
R6′为氢;并且
R7和R7′独立地为氢或卤素。
在一些实施方案中,式(I)的化合物为
其中
R2为氯、甲氧基、乙烯基、或1-丙烯基;
R3和R4为氢;并且
X为CF。
在一些实施方案中:
R1为炔丙基;并且
式(I)的化合物为
在一些实施方案中:
R1为氰甲基;
式(I)的化合物为
III。制备方法
用于合成其中X为CH或CF且R1为H的4-氨基-6-(杂环)吡啶甲酸和其中X为N且R1为H的6-氨基-2-(杂环)嘧啶羧酸的程序描述于授予Eckelbarger等人的美国专利9,637,505中,其全部内容通过引用并入本文。
用于合成其中R1、R2、R3、R4、R5、R6、R6’、R7、R7’和R8如上文所定义的式(I)的化合物的程序在方案1中示出
方案1
可以通过酯化反应将酸1-1转化为式(I)的化合物(方案1,步骤a)。酯可通过以下方式制备:使用任意数量的合适活性剂如用于肽偶联的那些(包括二环己基碳二亚胺(DCC)或羰基二咪唑(CDI))使酸与醇偶联;在如三乙胺或碳酸锂或碳酸钾的碱的存在下使酸与烷化剂反应,所述烷化剂如经取代或未经取代的烷基卤、经取代或未经取代的炔基卤、经取代或未经取代的氰基炔基卤、或经取代或未经取代的烷基磺酸盐;使酸的对应酰基氯与适当的醇反应;或在酸催化剂的存在下使对应的酸与适当的醇反应。所述反应可以在极性非质子溶剂如二甲基亚砜、N,N-二甲基甲酰胺、二氯甲烷、或1,2-二氯乙烷中进行。
IV.混合物
在一些实施方案中,本文提供的化合物、组合物和方法与一种或多种其他除草剂结合使用,以控制多种不期望植被。当与其他除草剂结合使用时,本文所述的化合物可与一种或多种其他除草剂调配在一起,或与一种或多种其他除草剂进行罐混或与一种或多种其他除草剂顺序施用。可以与本公开的化合物结合使用的一些除草剂包括但不限于4-CPA;4-CPB;4-CPP;2,4-D;2,4-D胆碱盐;2,4-D酯和胺;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(acetochlor)、三氟羧草醚(acifluorfen)、苯草醚(aclonifen)、丙烯醛(acrolein)、草不绿(alachlor)、草毒死(allidochlor)、亚汰草(alloxydim)、烯丙醇、阿罗酸(alorac)、特津酮(ametridione)、莠灭净(ametryn)、特草嗪酮(amibuzin)、胺唑草酮(amicarbazone)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、杀草强(amitrole)、氨基磺酸铵、莎稗磷(anilofos)、疏草隆(anisuron)、黄草灵(asulam)、莠去通(atraton)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、叠氮净(aziprotryne)、燕麦灵(barban)、BCPC、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、苯卡巴腙(bencarbazone)、氟草胺(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron-methyl)、地散磷(bensulide)、禾草丹(benthiocarb)、灭草松钠(bentazon-sodium)、胺酸杀(benzadox)、双苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、氟草黄(benzofluor)、新燕灵(benzoylprop)、塞草隆(benzthiazuron)、氟吡草酮(bicyclopyrone)、甲羧除草醚(bifenox)、双丙胺磷(bilanafos)、双草醚钠(bispyribac-sodium)、硼砂、除草定(bromacil)、糠草腈(bromobonil)、溴丁酰草胺(bromobutide)、杀草全(bromofenoxim)、溴苯腈(bromoxynil)、溴杀草敏(brompyrazon)、去草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、三环塞草胺(buthidazole)、丁噻隆(buthiuron)、比达宁(butralin)、丁氧环酮(butroxydim)、播土隆(buturon)、苏达灭(butylate)、二甲胂酸(cacodylic acid)、苯唑酮(cafenstrole)、氯酸钙、钙氰胺、克草胺酯(cambendichlor)、威磺灵(carbasulam)、草长灭(carbetamide)、特唑威(carboxazole)、唑草酮(carfentrazone-ethyl)、CDEA、CEPC、甲氧除草醚(chlomethoxyfen)、草灭平(chloramben)、地快乐(chloranocryl)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯溴隆(chlorbromuron)、氯草灵(chlorbufam)、乙氧苯隆(chloreturon)、伐草克(chlorfenac)、燕麦酯(chlorfenprop)、氟咪杀(chlorflurazole)、整形醇(chlorflurenol)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、草枯醚(chlornitrofen)、三氯丙酸(chloropon)、绿麦隆(chlorotoluron)、枯草隆(chloroxuron)、氯二甲酚(chloroxynil)、草败死(chlorprocarb)、氯普芬(chlorpropham)、氯磺隆(chlorsulfuron)、大克草(chlorthal)、草克乐(chlorthiamid)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、西速隆(cinosulfuron)、咯草隆(cisanilide)、氯酰草膦(clacyfos)、克草同(clethodim)、氯碘吡啶酯(cliodinate)、炔丙基炔草酯(clodinafop-propargyl)、可落弗(clofop)、广灭灵(clomazone)、氯甲酰草胺(clomeprop)、果美生长素(cloprop)、氯丙杀草(cloproxydim)、毕克草(clopyralid)、氯酯磺草胺(cloransulam-methyl)、CMA、硫酸铜、CPMF、CPPC、必灭草(credazine)、甲酚(cresol)、草隆(cumyluron)、氰草净(cyanatryn)、氰乃净(cyanazine)、环草敌(cycloate)、环比拉尼(cyclopyranil)、环比瑞摩(cyclopyrimorate)、环磺隆(cyclosulfamuron)、环杀草(cycloxydim)、环莠隆(cycluron)、丁基赛伏草(cyhalofop-butyl)、牧草快(cyperquat)、环丙津(cyprazine)、三环噻草胺(cyprazole)、环草胺(cypromid)、杀草隆(daimuron)、茅草枯(dalapon)、棉隆(dazomet)、异丁草胺(delachlor)、甜菜安(desmedipham)、敌草净(desmetryn)、燕麦敌(di-allate)、汰克草(dicamba)、二氯苯腈(dichlobenil)、氯全隆(dichloralurea)、苄胺灵(dichlormate)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸-P(dichlorprop-P)、禾草灵(diclofop)、双氯磺草胺(diclosulam)、二乙除草双(diethamquat)、乙酰甲草胺(diethatyl)、戊味禾草灵(difenopenten)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟草胺(diflufenican)、氟吡草腙(diflufenzopyr)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊净(dimethametryn)、汰草灭(dimethenamid)、甲酚噻草胺-P(dimethenamid-P)、草灭散(dimexano)、草哒酮(dimidazon)、敌乐胺(dinitramine)、地乐特(dinofenate)、硝丙酚(dinoprop)、戊硝酚(dinosam)、达诺杀(dinoseb)、特乐酚(dinoterb)、
草乃敌(diphenamid)、异丙净(dipropetryn)、敌草快(diquat)、赛松(disul)、汰硫草(dithiopyr)、达有龙(diuron)、DMPA、DNOC、DSMA、EBEP、甘草津(eglinazine)、草多索(endothal)、三唑磺(epronaz)、EPTC、抑草蓬(erbon)、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、乙柳酰胺(ethbenzamide)、胺苯磺隆(ethametsulfuron)、磺噻隆(ethidimuron)、硫草敌(ethiolate)、ethobenzamid、乙氧苯草胺(etobenzamid)、益覆灭(ethofumesate)、氯氟草醚(ethoxyfen)、乙氧嘧磺隆(ethoxysulfuron)、硝草酚(etinofen)、乙胺草醚(etnipromid)、乙氧苯草胺(etobenzanid)、EXD、酰苯磺威(fenasulam)、涕丙酸(fenoprop)、唑啉草酯(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P-ethyl)、精噁唑禾草灵+双苯噁唑酸(isoxadifen-ethyl)、芬诺杀磺隆(fenoxasulfone)、fenquinotrione、氯苯氧乙醇(fenteracol)、噻唑禾草灵(fenthiaprop)、四唑酰草胺(fentrazamide)、非草隆(fenuron)、硫酸亚铁、麦燕灵(flamprop)、麦草伏M(flamprop-M)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen-benzyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P-butyl)、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟苯吡草(flufenican)、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、三氟噁嗪(flumezin)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、伏草隆(fluometuron)、三氟硝草醚(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)、flupropacil、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草烟(fluroxypyr)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、氟磺胺草醚(fomesafen)、甲酰胺磺隆(foramsulfuron)、杀木膦(fosamine)、呋氧草醚(furyloxyfen)、固杀草(glufosinate)、草铵膦(glufosinate-ammonium)、草甘膦(glyphosate)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron-methyl)、氟啶草(haloxydine)、甲基合氯氟(haloxyfop-methyl)、精吡氟氯禾灵(haloxyfop-P-methyl)、氟氯吡啶酯(halauxifen-methyl)、六氯丙酮、六氟盐、环嗪酮(hexazinone)、咪草酸(imazamethabenz)、甲氧咪草烟(imazamox)、甲咪唑烟酸(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、碘草臆(iodobonil)、碘甲烷、碘甲磺隆(iodosulfuron)、碘嗪磺隆(iofensulfuron)、碘苯腈(ioxynil)、草怕津(ipazine)、三唑酰草胺(ipfencarbazone)、丙草定(iprymidam)、草特灵(isocarbamid)、异草定(isocil)、丁嗪草酮(isomethiozin)、异草完隆(isonoruron)、异丙灵(isopolinate)、异乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、异噁唑草酮(isoxaflutole)、异噁草醚(isoxapyrifop)、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、lancotrione、环草定(lenacil)、利谷隆(linuron)、MAA、MAMA、MCPA酯和胺、酚硫杀(MCPA-thioethyl)、MCPB、
2-甲-4-氯丙酸(mecoprop)、精2-甲-4-氯丙酸(mecoprop-P)、地乐施(medinoterb)、苯噻草胺(mefenacet)、氟磺酰草胺(mefluidide)、灭莠津(mesoprazine)、甲基二磺隆(mesosulfuron)、硝磺草酮(mesotrione)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、二甲哒草伏(metflurazon)、噻唑隆(methabenzthiazuron)、氟烯硝草(methalpropalin)、灭草唑(methazole)、甲硫苯威(methiobencarb)、异噁噻草醚(methiozolin)、灭草恒(methiuron)、醚草通(methometon)、盖草津(methoprotryne)、溴甲烷、异硫氰酸甲酯、甲基杀草隆(methyldymron)、吡喃隆(metobenzuron)、秀谷隆(metobromuron)、异丙甲草胺(metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、赛克津(metribuzin)、甲磺隆(metsulfuron)、草达灭(molinate)、庚酰草胺(monalide)、特噁唑隆(monisouron)、一氯乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、灭草隆(monuron)、伐草快(morfamquat)、MSMA、萘丙胺(naproanilide)、敌草胺(napropamide)、精敌草胺(napropamide-M)、抑草生(naptalam)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟氯草胺(nipyraclofen)、磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、达草灭(norflurazon)、草完隆(noruron)、OCH、坪草丹(orbencarb)、邻二氯苯、嘧苯胺磺隆(orthosulfamuron)、黄草消(oryzalin)、丙炔噁草酮(oxadiargyl)、恶草灵(oxadiazon)、草哒松(oxapyrazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、吡草醚(paraflufen-ethyl)、对氟隆(parafluron)、百草枯(paraquat)、克草猛(pebulate)、壬酸(pelargonic acid)、二甲戊乐灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorophenol)、甲氯酰草胺(pentanochlor)、戊基噁唑酮(pentoxazone)、黄草伏(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、乙基甜菜宁(phenmedipham-ethyl)、稀草隆(phenobenzuron)、醋酸苯汞、毒莠定(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、亚砷酸钾、叠氮化钾、氰酸钾、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron-methyl)、环丙腈津(procyazine)、胺氟乐灵(prodiamine)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、环苯草酮(profoxydim)、甘扑津(proglinazine)、调环酸钙(prohexadione-calcium)、扑灭通(prometon)、扑草净(prometryn)、扑草胺(propachlor)、敌稗(propanil)、喔草酯(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙嗪嘧磺隆(propyrisulfuron)、拿草特(propyzamide)、草硫亚胺(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、扑灭生(proxan)、丙炔草胺(prynachlor)、比达农(pydanon)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、磺酰草吡唑(pyrasulfotole)、双唑草腈(pyrazogyl)、吡唑特(pyrazolynate)、吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、嘧啶肟草醚(pyribenzoxim)、稗草畏(pyributicarb)、氯草定(pyriclor)、氯苯哒醇(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、吡丙醚(pyrimisulfan)、嘧硫草醚-甲基(pyrithiobac-methyl)、砜吡草唑(pyroxasulfone)、啶磺草胺(pyroxsulam)、快杀稗(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P-ethyl)、硫氰苯胺(rhodethanil)、玉嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、异丙甲草胺(S-metolachlor)、另丁津(sebuthylazine)、仲丁通(secbumeton)、稀禾定(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西玛通(simeton)、西草净(simetryn)、SMA、亚砷酸钠、叠氮化钠、氯酸钠、磺草酮(sulcotrione)、草克死(sulfallate)、甲磺草胺(sulfentrazone)、嘧磺隆(sulfometuron)、草硫膦(sulfosate)、磺酰磺隆(sulfosulfuron)、硫酸、吖庚磺酯(sulglycapin)、灭草灵(swep)、TCA、牧草胺(tebutam)、丁唑隆(tebuthiuron)、特呋三酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、四氟隆(tetrafluron)、甲氧噻草胺(thenylchlor)、噻氟隆(thiazafluron)、噻草啶(thiazopyr)、噻二唑草胺(thidiazimin)、苯基噻二唑脲(thidiazuron)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、禾草丹(thiobencarb)、三氟嘧磺草胺(tiafenacil)、伸草丹(tiocarbazil)、嘧草胺(tioclorim)、tolpyralate、苯唑草酮(topramezone)、肟草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、杀草畏(tricamba)、绿草定酯和胺、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟草嗪(trifludimoxazin)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三聚氰酸(trihydroxytriazine)、三甲隆(trimeturon)、茚草酮(tripropindan)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、灭草猛(vernolate)和二甲苯草胺(xylachlor)。一种或多种混合配伍物可以配制为游离酸或碱或配制为如上文所定义的盐或酯。
本文所述的化合物和组合物通常可以与已知的除草剂安全剂组合使用,如解草酮(benoxacor)、禾草丹(benthiocarb)、芸苔素内酯(brassinolide)、解草酯(cloquintocet)(例如,解毒喹(mexyl))、解草胺腈(cyometrinil)、杀草隆(daimuron)、二氯丙烯胺(dichlormid)、二环酮(dicyclonon)、哌草丹(dimepiperate)、乙拌磷(disulfoton)、解草唑(fenchlorazole-ethyl)、解草啶(fenclorim)、解草安(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、超敏蛋白、双苯噁唑酸(isoxadifen-ethyl)、吡唑解草酯(mefenpyr-diethyl)、2-二氯甲基-2-甲基-1,3-二氧戊环(也称为MG 191)、二氯乙酰基-1-氧杂-4-氮杂螺(4,5)-癸烷(也称为MON 4660)、萘二甲酸酐(NA)、解草腈(oxabetrinil)、(R,S)-3-二氯乙酰基-2,2,5-三甲基噁唑烷(也称为R-29148)、metcamifen、N-苯基磺酰基苯甲酰胺、或它们的混合物,以提高它们的选择性。
在一些实施方案中,本文提供的化合物可以以包含除草有效量的化合物以及至少一种农业上可接受的佐剂或载剂的混合物的形式使用。示例性的佐剂或载剂包括不对有价值的作物具有植物毒性或具有明显的植物毒性,例如在为了在存在作物的情况下进行选择性杂草控制而施用所述组合物时所采用的浓度下,和/或不与本文提供的化合物或其他组合物成分发生化学反应或发生明显的化学反应的那些。此类混合物可以被设计成直接施用于杂草或它们的所在地,或可以是在施用前用另外的载剂和佐剂稀释的浓缩物或制剂。它们可以是固体如粉尘、颗粒、水可分散性颗粒或可湿性粉末,或液体如可乳化浓缩物、溶液、乳液或悬浮液。它们还可以作为预混物提供或进行罐混。
可用于制备本公开的除草剂混合物的合适的农业佐剂和载剂是本领域技术人员熟知的。这些佐剂中的一些包括但不限于作物油浓缩物(矿物油(85%)+乳化剂(15%));壬基酚乙氧基化物;苄基椰油烷基二甲基季铵盐;石油烃、烷基酯、有机酸和阴离子表面活性剂的混合物;C9-C11烷基多糖苷;磷酸化醇乙氧基化物;天然伯醇(C12-C16)乙氧基化物;二仲丁基苯酚EO-PO嵌段共聚物;甲基封端的聚硅氧烷(polysiloxane-methyl cap);壬基酚乙氧基化物+尿素硝酸铵;乳化的甲基化种子油;十三醇(合成)乙氧基化物(8EO);牛油胺乙氧基化物(15EO);PEG(400)二油酸酯-99。
可采用的液体载剂包括水和有机溶剂。示例性有机溶剂包括但不限于石油馏分或烃如矿物油、芳族溶剂、石蜡油等;植物油如大豆油、菜籽油、橄榄油、蓖麻油、葵花籽油、椰子油、玉米油、棉籽油、亚麻籽油、棕榈油、花生油、红花油、芝麻油、桐油等;上述植物油的酯;一元醇或二元醇、三元醇或其他低级多元醇(含4-6个羟基)的酯,如2-乙基己基硬脂酸酯、油酸正丁酯、肉豆蔻酸异丙酯、二油酸丙二醇酯、琥珀酸二辛酯、己二酸二丁酯、邻苯二甲酸二辛酯等;一羧酸、二羧酸和多羧酸的酯等。特定的有机溶剂包括甲苯、二甲苯、石脑油、作物油、丙酮、甲基乙基酮、环己酮、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇单甲醚和二甘醇单甲醚、甲醇、乙醇、异丙醇、戊醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮、N,N-二甲基烷基酰胺、二甲基亚砜、液态肥料等。在一些实施方案中,水是用于稀释浓缩物的载剂。
合适的固体载剂包括滑石、叶蜡石粘土、二氧化硅、美国活性陶土(attapulgusclay)、高岭土、硅藻土(kieselguhr)、白垩、含硅藻的土(diatomaceous earth)、石灰、碳酸钙、膨润土、漂白土、棉籽壳、小麦粉、大豆粉、浮石、木粉、胡桃壳粉、木质素等。合适的固体载剂还可包括上述固体载剂的组合。
在一些实施方案中,一种或多种表面活性剂用于本公开的组合物中。在一些实施方案中,此类表面活性剂用于固体组合物和液体组合物两者中,例如,被设计成在施用前用载剂稀释的那些。表面活性剂可为阴离子性的、阳离子性的或非离子性的,并且可用作乳化剂、润湿剂、悬浮剂或用于其他目的。制剂领域常用的并且也可用于本发明制剂的表面活性剂尤其在McCutcheon’s Detergents and Emulsifiers Annual,MC Publishing Corp.,Ridgewood,New Jersey,1998以及在Encyclopedia of Surfactants,第I-III卷,ChemicalPublishing Co.,New York,1980-81中有所描述。典型的表面活性剂包括烷基硫酸盐,如月桂基硫酸二乙醇铵;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚-烯化氧加成产物,如壬基酚-C18乙氧基化物;醇烯化氧加成产物,如十三醇-C16乙氧基化物;皂类,如硬脂酸钠;烷基萘-磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯盐,如二(2-乙基己基)磺基琥珀酸钠;山梨醇酯,如山梨醇油酸酯;季胺,如月桂基三甲基氯化铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷与环氧丙烷的嵌段共聚物;单烷基和二烷基磷酸酯的盐;植物或种子油,如大豆油、菜籽/芥花油、橄榄油、蓖麻油、葵花籽油、椰子油、玉米油、棉籽油、亚麻籽油、棕榈油、花生油、红花油、芝麻油、桐油等;以及上述植物油的酯,例如甲酯。
通常,这些材料中的一些如植物或种子油以及它们的酯可互换地用作农业佐剂、液体载剂或表面活性剂。
常用于农业组合物的其他佐剂包括相容剂、消泡剂、多价螯合剂、中和剂以及缓冲剂、腐蚀抑制剂、染料、增味剂、铺展剂、渗透助剂、粘着剂、分散剂、增稠剂、防冻剂、抗微生物剂等。所述组合物还可含有其他可相容的组分,例如,其他除草剂、植物生长调节剂、杀真菌剂、杀虫剂等,并且可与液态肥料或固态、微粒肥料载剂,如硝酸铵、尿素等,调配在一起。
本公开的除草剂组合物中活性成分的浓度通常为约0.001重量%至约98重量%。通常使用约0.01重量%至约90重量%的浓度。在设计用作浓缩物的组合物中,活性成分通常以约5重量%至约98重量%,优选地约10重量%至约90重量%的浓度存在。此类组合物通常在施用前用惰性载剂如水稀释。常施用于杂草或杂草所在地的经稀释的组合物通常含有约0.0001重量%至约1重量%的活性成分,且优选地含有约0.001重量%至约0.05重量%。
如本文所用,与量结合使用的修饰语“约”包括所述值,并且具有由上下文规定的含义(例如,它至少包括与特定量的测量相关的误差度)。当在范围的上下文中使用时,修饰语“约”也应视为公开了由两个端点的绝对值限定的范围。例如,范围“约2至约4”也公开了范围“2至4”。
V.施用方法
本发明的组合物可以通过使用常规的地面或空中洒粉器、喷雾器和颗粒施用器、通过添加到灌溉用水或稻田水(flood water)中以及通过本领域技术人员已知的其他常规方式施用于杂草或其所在地。
在一些实施方案中,本文所述的本发明的化合物和组合物以苗后施用、苗前施用、水中施用方式施用至淹水的稻田水稻或水体(例如,池塘、湖或溪流)中,或焚毁施用。
在一些实施方案中,本文提供的化合物和组合物用于控制作物和非作物场所中的杂草,所述作物包括但不限于柑橘类、苹果、橡胶、棕榈油、林业、直播稻、水播稻和移植稻、小麦、大麦、燕麦、黑麦、高粱、玉米(corn/maize)、牧地、牧草地、牧场、休耕地、草皮、乔木和藤本果园、水生植物、或中耕作物(row-crops),并且所述非作物场所例如工业植被管理或道路周围。在一些实施方案中,化合物和组合物用于控制木质植物、阔叶和禾本科杂草或莎草。
在一些实施方案中,本文提供的化合物和组合物用于控制水稻中的不期望植被。在某些实施方案中,不期望植被是臂形草(Brachiaria platyphylla (Groseb.)Nash(阔叶信号草(broadleaf signalgrass),BRAPP)、马唐(Digitaria sanguinalis(L)Scop.)(红色马唐(large crabgrass),DIGSA)、稗(Echinochloa crus-galli(L.)P.Beauv.)(稗草(barnyardgrass),ECHCG)、光头稗(Echinochloa colonum(L.)LINK)(光头稗(junglerice),ECHCO)、水田稗(Echinochloa oryzoides(Ard.)Fritsch)(早水草(earlywatergrass),ECHOR)、空心稗(Echinochloa oryzicola(Vasinger)Vasinger)(晚水草(late watergrass),ECHPH)、田间鸭嘴草(Ischaemum rugosum Salisb.)(鸭嘴草(saramollagrass),ISCRU)、千金子(Leptochloa chinensis(L.)Nees)(中国千金子(Chinese sprangletop),LEFCH)、丛生千金子(Leptochloa fascicularis(Lam.)Gray)(有芒千金子(bearded sprangletop),LEFFA)、类黍千金子(Leptochloa panicoides(Presl.)Hitchc.)(亚马逊千金子(Amazon sprangletop),LEFPA)、洋野黍(Panicumdichotomiflorum(L.)Michx.)(秋黍(fall panicum),PANDI)、毛花雀稗(Paspalumdilatatum Poir.)(雀稗草(dallisgrass),PASDI)、异型莎草(Cyperus difformis L.)(小花莎草(smallflower flatsedge),CYPDI)、油莎草(Cyperus esculentus L.)(黄莎草(yellow nutsedge),CYPES)、碎米莎草(Cyperus iria L.)(米莎草(rice flatsedge),CYPIR)、香附子(Cyperus rotundus L.)(紫莎草(purple nutsedge),CYPRO)、荸荠属物种(Eleocharis species)(ELOSS)、水虱草(Fimbristylis miliacea(L.)Vahl)(水虱草(globe fringerush),FIMMI)、萤蔺(Schoenoplectus juncoides Roxb.)(日本芦苇(Japanese bulrush),SPCJU)、海滨三棱草(Schoenoplectus maritimus L.)(云林莞草(sea clubrush),SCPMA)、水毛花(Schoenoplectus mucronatus L.)(稻田芦苇(ricefieldbulrush),SCPMU)、合萌属物种(Aeschynomene species)(合萌(jointvetch),AESSS)、喜旱莲子草(Alternanthera philoxeroides(Mart.)Griseb.)(空心莲子草(alligatorweed),ALRPH)、泽泻水生车前草属(Alisma plantago-aquatica L.)(普通水生车前草(commonwaterplantain),ALSPA)、苋属物种(Amaranthus species)(藜(pigweeds)和苋(amaranths),AMASS)、红水苋(Ammannia coccinea Rottb.)(红茎(redstem),AMMCO)、旱莲草(Eclipta alba(L.)Hassk.)(美国假菊(American false daisy),ECLAL)、沼生异蕊花(Heteranthera limosa(SW.)Willd./Vahl)(鸭沙拉(ducksalad),HETLI)、肾形异蕊花(Heteranthera reniformis R.&P.)(圆叶异蕊花属(roundleaf mudplantain),HETRE)、碗仔花(Ipomoea hederacea(L.)Jacq.)(裂叶牵牛(ivyleaf morningglory),IPOHE)、美洲母草(Lindernia dubia(L.)Pennell)(low false pimpernel,LIDDU)、雨久花(Monochoriakorsakowii Regel&Maack)(雨久花属(monochoria),MOOKA)、鸭舌草(Monochoriavaginalis(Burm.F.)C.Presl ex Kuhth)(雨久花属,MOOVA)、裸花水竹叶(Murdannianudiflora(L.)Brenan)(鹤草(doveweed),MUDNU)、宾夕法尼亚蓼属(Polygonumpensylvanicum L.)(宾夕法尼亚荨麻(Pennsylvania smartweed),POLPY)、春蓼(Polygonum persicaria L.)(桃叶蓼(ladysthumb),POLPE)、辣椒蓼(Polygonumhydropiperoides Michx.)(POLHP,软蓼(mild smartweed))、节节菜(Rotala indica(Willd.)Koehne)(圆叶节节菜(Indian toothcup),ROTIN)、慈菇属物种(Sagittariaspecies)(慈菇(arrowhead),SAGSS)、田菁(Sesbania exaltata(Raf.)Cory/Rydb.ExHill)(大果田菁(hemp sesbania),SEBEX)或尖瓣花(Sphenoclea zeylanica Gaertn.)(楔瓣花(gooseweed),SPDZE)。
在一些实施方案中,本文提供的化合物和组合物用于控制谷物中的不期望植被。在某些实施方案中,不期望植被为大穗看麦娘(Alopecurus myosuroides Huds.)(黑草(blackgrass),ALOMY)、阿披拉草(Apera spica-venti(L.)Beauv.)(盘固拉草(windgrass),APESV)、野燕麦(Avena fatua L.)(野燕麦(wild oat),AVEFA)、旱雀麦(Bromus tectorum L.)(丘原雀麦草(downy brome),BROTE)、多花黑麦草(Loliummultiflorum Lam.)(意大利黑麦草(Italian ryegrass),LOLMU)、小子虉草(Phalarisminor Retz.)(小种金黄草(littleseed canarygrass),PHAMI)、早熟禾(Poa annua L.)(一年生蓝草(annual bluegrass),POAAN)、金色狗尾草(Setaria pumila(Poir.)Roemer&J.A.Schultes)(黄色狗尾草(yellow foxtail),SETLU)、狗尾草(Setaria viridis(L.)Beauv.)(绿色狗尾草(green foxtail),SETVI)、丝路蓟(Cirsium arvense(L.)Scop.)(加拿大蓟(Canada thistle),CIRAR)、八仙草(Galium aparine L.)(猪殃殃(catchweedbedstraw),GALAP)、地肤(Kochia scoparia(L.)Schrad.)(地肤属(kochia),KCHSC)、紫花野芝麻(Lamium purpureum L.)(紫色枯荨麻(purple deadnettle),LAMPU)、母菊(Matricaria recutita L.)(野甘菊(wild chamomile),MATCH)、同花母菊(Matricariamatricarioides(Less.)Porter)(香甘菊(pineappleweed),MATMT)、虞美人(Papaverrhoeas L.)(普通罂粟(common poppy),PAPRH)、卷茎蓼(Polygonum convolvulus L.)(野生荞麦(wild buckwheat),POLCO)、刺沙蓬(Salsola tragus L.)(俄罗斯蓟(Russianthistle),SASKR)、繁缕(Stellaria media(L.)Vill.)(普通繁缕(common chickweed),STEME)、阿拉伯婆婆纳(Veronica persica Poir.)(波斯婆婆纳(Persian speedwell),VERPE)、野生堇菜(Viola arvensis Murr.)(田地紫罗兰(field violet),VIOAR)或三色堇(Viola tricolor L.)(野生紫罗兰,VIOTR)。
在一些实施方案中,本文提供的化合物和组合物用于控制某范围和牧地中的不期望植被。在某些实施方案中,不期望植被是豚草(Ambrosia artemisiifolia L.)(普通豚草(common ragweed),AMBEL)、决明子(Cassia obtusifolia)(sickle pod,CASOB)、矢车菊(Centaurea maculosa auct.non Lam.)(斑点矢车菊(spotted knapweed),CENMA)、丝路蓟(Cirsium arvense(L.)Scop.)(加拿大蓟(Canada thistle),CIRAR)、田旋花(Convolvulusarvensis L.)(野生旋花(field bindweed),CONAR)、乳浆大戟(Euphorbia esula L.)(乳浆草(leafy spurge),EPHES)、毒莴苣(Lactuca serriola L./Torn.)(多刺莴苣(pricklylettuce),LACSE)、长叶车前(Plantago lanceolata L.)(鹿角车前(buckhorn plantain),PLALA)、钝叶酸模(Rumex obtusifolius L.)(阔叶羊蹄(broadleaf dock),RUMOB)、刺金午时花(Sida spinosa L.)(prickly sida,SIDSP)、欧白芥(Sinapis arvensis L.)(野生芥菜(wild mustard),SINAR)、苣荬菜(Sonchus arvensis L.)(多年生苦苣菜(perennialsowthistle),SONAR)、一枝黄花属物种(Solidago species)(秋麒麟草属(goldenrod),SOOSS)、蒲公英(Taraxacum officinale G.H.Weber ex Wiggers)(蒲公英(dandelion),TAROF)、白车轴草(Trifolium repens L.)(白三叶草(white clover),TRFRE)或刺荨麻(Urtica dioica L.)(普通荨麻(common nettle),URTDI)。
在一些实施方案中,本文提供的化合物和组合物用于控制中耕作物中发现的不期望植被。在某些实施方案中,不期望植被是大穗看麦娘(Alopecurus myosuroides Huds.)(黑草(blackgrass),ALOMY)、野燕麦(Avena fatua L.)(野燕麦(wild oat),AVEFA)、臂形草(Brachiaria platyphylla(Groseb.)Nash)(阔叶信号草(broadleaf signalgrass),BRAPP)、马唐(Digitaria sanguinalis(L.)Scop.)(大马唐草(large crabgrass),DIGSA)、稗(Echinochloa crus-galli(L.)P.Beauv.)(稗草(barnyardgrass),ECHCG)、光头稗(Echinochloa colonum(L.)Link)(光头稗(junglerice),ECHCO)、多花黑麦草(Loliummultiflorum Lam.)(意大利黑麦草(Italian ryegrass),LOLMU)、洋野黍(Panicumdichotomiflorum Michx.)(秋黍(fall panicum),PANDI)、稷(Panicum miliaceum L.)(野生小米黍(wild-proso millet),PANMI)、大狗尾草(Setaria faberi Herrm.)(谷莠子(giant foxtail),SETFA)、狗尾草(Setaria viridis(L.)Beauv.)(绿狗尾草(greenfoxtail),SETVI)、约翰逊草(Sorghum halepense(L.)Pers.)(约翰逊草(Johnsongrass),SORHA)、蜀黍(Sorghum bicolor(L.)Moench ssp.Arundinaceum)(shattercane,SORVU)、油莎草(Cyperus esculentus L.)(黄莎草(yellow nutsedge),CYPES)、香附子(Cyperusrotundus L.)(紫莎草(purple nutsedge),CYPRO)、苘麻(Abutilon theophrasti Medik.)(绒毛叶(velvetleaf),ABUTH)、苋属物种(Amaranthus species)(藜(pigweeds)和苋(amaranths),AMASS)、豚草(Ambrosia artemisiifolia L.)(普通豚草(common ragweed),AMBEL)、多年生豚草(Ambrosia psilostachya DC.)(西方豚草(western ragweed),AMBPS)、三裂叶豚草(Ambrosia trifida L.)(大豚草(giant ragweed),AMBTR)、叙利亚马利筋(Asclepias syriaca L.)(普通乳草(common milkweed),ASCSY)、藜草(Chenopodiumalbum L.)(普通灰菜(common lambsquarters),CHEAL)、丝路蓟(Cirsium arvense(L.)Scop.)(加拿大蓟(Canada thistle),CIRAR)、圆叶鸭跖草(Commelina benghalensis L.)(饭包草(tropical spiderwort),COMBE)、曼陀罗(Datura stramonium L.)(曼陀罗(jimsonweed),DATST)、胡萝卜(Daucus carota L.)(野生胡萝卜(wild carrot),DAUCA)、白苞猩猩草(Euphorbia heterophylla L.)(野生一品红(wild poinsettia),EPHHL)、香丝草(Erigeron bonariensis L.)(毛飞蓬(hairy fleabane),ERIBO)、加拿大蓬(Erigeroncanadensis L.)(加拿大飞蓬(Canadian fleabane),ERICA)、向日葵(Helianthus annuusL.)(普通向日葵(common sunflower),HELAN)、苞叶小牵牛(Jacquemontia tamnifolia(L.)Griseb.)(小花牵牛(smallf lower morningglory),IAQTA)、碗仔花(Ipomoeahederacea(L.)Jacq.)(裂叶牵牛(ivyleaf morningglory),IPOHE)、小白花牵牛(Ipomoealacunosa L.)(白牵牛(white morningglory),IPOLA)、毒莴苣(Lactuca serriola L./Torn.)(多刺萬苣(prickly lettuce),LACSE)、马齿苋(Portulaca oleracea L.)(普通马齿苋(common purslane),POROL)、刺金午时花(Sida spinosa L.)(prickly sida,SIDSP)、欧白芥(Sinapis arvensis L.)(野生芥菜(wild mustard),SINAR)、光果龙葵(Solanumptychanthum Dunal)(美东龙葵(eastern black nightshade),SOLPT)或苍耳子(Xanthiumstrumarium L.)(普通苍耳(common cocklebur),XANST)。
在一些实施方案中,在苗后操作中使用约1至约4,000克/公顷(g/ha)的施用率。在一些实施方案中,在苗前操作中使用约1至约4,000g/ha的施用率。
本文所述的化合物、组合物和方法用于在以下作物中控制不期望的植被:5-烯醇丙酮酸莽草酸-3-磷酸(EPSP)合酶抑制剂耐受性(例如,草甘膦耐受性)、谷氨酰胺合成酶抑制剂耐受性(例如,草铵膦耐受性)、合成生长素耐受性(例如,麦草畏耐受性、苯氧基生长素耐受性、吡啶氧基生长素耐受性)、生长素转运抑制剂耐受性、乙酰辅酶A羧化酶(ACCase)抑制剂耐受性(例如,芳氧基苯氧基丙酸酯耐受性)、乙酰乳酸合酶(ALS)或乙酰羟酸合酶(AHAS)抑制剂耐受性(例如,咪唑啉酮耐受性、磺酰脲耐受性、嘧啶基硫代苯甲酸酯耐受性、三唑并嘧啶耐受性、磺酰基氨基羰基三唑啉酮耐受性)、4-羟苯基-丙酮酸双加氧酶(HPPD)抑制剂耐受性、原卟啉原氧化酶(PPO)抑制剂耐受性、光系统(PS)II抑制剂耐受性(例如,三嗪耐受性和溴苯腈耐受性)作物(如但不限于大豆、棉花、芥菜/油菜、水稻、谷物、玉米、草皮等),例如,结合EPSP合酶抑制剂(例如,草甘膦)、谷氨酰胺合成酶抑制剂(例如,草铵膦)、合成生长素(例如,麦草畏、苯氧基生长素、吡啶氧基生长素)、ACCase抑制剂(例如,芳氧基苯氧基丙酸酯)、ALS抑制剂(例如,咪唑啉酮、磺酰脲类、嘧啶基硫代苯甲酸酯、三唑并嘧啶和磺酰基氨基羰基三唑啉酮)、HPPD抑制剂、PPO抑制剂和PS II抑制剂(例如,三嗪和溴苯腈)。所述组合物和方法可用于控制具有赋予对多种作用模式的多种化学品和/或抑制剂的耐受性的多种或堆叠性状的作物中的不期望植被。
本文提供的化合物和组合物还可用于控制除草剂抗性或耐受性杂草。示例性抗性或耐受性杂草包括但不限于对以下物质具有抗性或耐受性的生物型:ALS(或AHAS)抑制剂、PS II抑制剂、ACCase抑制剂、合成生长素、PS I抑制剂、EPSP合酶抑制剂、微管组装抑制剂、脂质合成抑制剂、PPO抑制剂、类胡萝卜素生物合成抑制剂、极长链脂肪酸(VLCFA)抑制剂、八氢番茄红素脱氢酶(PDS)抑制剂、谷氨酰胺合成酶抑制剂、HPPD抑制剂、有丝分裂抑制剂、纤维素生物合成抑制剂、具有多种作用模式的除草剂如二氯喹啉酸,以及未分类的除草剂,如芳基氨基丙酸、野燕枯(difenzoquat)、茵多杀(endothall)和有机砷。示例性抗性或耐受性杂草包括但不限于对多种除草剂、多种化学品和多种除草剂作用模式具有抗性或耐受性的生物型。
所述的实施方案和下列实施例均出于示例性目的,而无意限制权利要求的范围。在不脱离受权利要求书保护的主题的精神和范围的情况下,相对于本文所述的组合物的其他修改形式、用途或组合将对本领域的普通技术人员显而易见。
实施例
实施例1:7-氟-1-(三异丙基甲硅烷基)-1H-吲哚(1)的制备
标题化合物根据以引用方式整体并入本文的文献程序Das,A.等人Org.Lett.2017,19,5794-5797制备。
实施例2:7-氟-6-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)-1-(三异丙基甲硅烷基)-1H-吲哚(2)的制备
如美国专利申请公布2014/0274695中的前体实施例3,制备50中所述制备标题化合物。
实施例3:4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸甲酯(3)的制备
可以如美国专利申请公布2014/0274695中的实施例1中所述制备标题化合物。另选地,可以如下制备所述标题化合物。
向装配有磁力搅拌器、冷凝器、内部温度探针和氮气气氛的3升(L)三颈烧瓶中添加4-氨基-3,6-二氯-5-氟吡啶甲酸甲酯(如Fields等人,Tetrahedron Letters 2010,51,79-81中所述的那样制备;75克(g),314毫摩尔(mmol))和7-氟-6-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)-1-(三异丙基甲硅烷基)-1H-吲哚(175g,377mmol)。顺序添加乙腈(CH3CN;1255毫升(mL))和2摩尔(M)磷酸钾溶液(314mL,628mmol)。然后将混合物抽真空并用氮气(3x)回填,然后添加双(三苯基膦)二氯化钯(11.12g,15.69mmol)。将烧瓶抽真空并回填(3x),并将混合物在65℃下加热。3小时(h)后,添加氟化钾(74.4g,1255mmol)并且再继续加热16h。使反应混合物冷却至室温并且通过硅藻土过滤。分离各相,并在减压下除去溶剂。将残余物用己烷研磨,并通过过滤收集固体,并用己烷洗涤。将所得固体用二氯甲烷(CH2Cl2)处理、过滤、用少量CH2Cl2冲洗,并在50℃下真空干燥。分离得到呈灰白色固体的标题化合物(73.5g,69%)。
实施例4:4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸(4)的制备
可以如美国专利申请公布2014/0274695中的实施例12中那样或如下制备标题化合物。
将4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸甲酯(288毫克(mg),0.853mmol)溶解于四氢呋喃(THF;2.0mL)、甲醇(CH3OH;2.0mL)和水(1.0mL)中。添加氢氧化锂水合物(100mg,2.383mmol)。使反应混合物在室温下搅拌过夜。将反应混合物浓缩至干燥。用水稀释所得固体,并使悬浮液呈酸性(pH~3)。用乙酸乙酯(EtOAc;3x)萃取悬浮液。将合并的有机萃取物用饱和氯化钠水溶液(NaCl)洗涤,置于硫酸镁(MgSO4)上干燥,过滤并浓缩。分离得到呈灰白色固体的标题化合物(256mg,93%)。
实施例5:4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸丙-2-炔-1-基酯(5)的制备
将4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸(1.5g,4.63mmol)、碳酸钾(0.833g,6.02mmol)和3-溴丙炔(0.549mL,5.10mmol)在N,N-二甲基甲酰胺(DMF;18.5mL)中的混合物在室温下搅拌4h。将反应混合物倒入碳酸氢钠(NaHCO3)的半饱和水溶液中,并用EtOAc(2x)萃取。将合并的有机萃取物置于MgSO4上干燥、过滤并浓缩。通过自动快速柱色谱法(硅胶,己烷/EtOAc梯度)纯化残余物。向所得油状物中添加最少量的CH2Cl2以引发结晶。超声处理用于促进进一步结晶。然后添加己烷以进一步沉淀产物。将固体过滤、用己烷(2x)洗涤并真空干燥。分离得到呈白色固体的标题化合物(1.33g,79%):mp 140–142℃;1HNMR(400MHz,CDCl3)δ8.49(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);19FNMR(376MHz,CDCl3)δ-135.47,-135.55,-137.23,-137.32;ESIMS m/z 362([M+H]+)。
如实施例5中那样合成以下化合物。
4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸氰甲酯(6)
分离得到呈白色固体的标题化合物(730mg,65%):mp 139–140℃;1H NMR(300MHz,DMSO-d6)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]+)。
实施例6:温室中苗后除草活性的评价
在表面积为103.2平方厘米(cm2)的塑料盆中,将所需测试植物物种的种子种植在Sun Gro306种植混合物中,所述种植混合物通常具有6.0至6.8的pH以及约30%的有机物含量。当要求确保良好萌芽和健康植物时,施加杀真菌剂处理和/或其他化学或物理处理。植物在温室中在大约14小时(h)光周期下生长7-36天(d),所述光周期在白天期间维持在约18℃且在夜晚期间维持在17℃。定期添加营养物质和水,并且视需要利用顶置式金属卤化物1000瓦灯提供补充照明。当植物达到第二或第三真叶期时,所述植物用于测试。
将所配制的化合物5(每升100克酸当量(g ae/L);乳油(EC))、化合物6(100g ae/L;EC)或化合物7(100g ae/L;EC)的等分试样置于25mL玻璃小瓶中,并稀释于一定体积的1.25%(体积/体积(v/v))的含水Actirob B酯化菜籽油中,以获得储备溶液。将浓缩的储备溶液用1.25%v/v的Actirob B酯化菜籽油的含水混合物稀释,以提供适当的施用率。化合物的需求量基于施用率为每公顷187升(L/ha)时的12毫升施用体积。将所配制的化合物施用于植物材料,采用的是顶置式Mandel轨道喷雾器,该喷雾器配备有8002E喷嘴,该喷嘴经校准在0.503平方米(m2)的施用面积上以187L/ha递送,喷雾高度为平均植物株冠之上18英寸(43厘米(cm))。以相同的方式用溶剂空白喷洒对照植物。
将经处理的植物和对照植物放置在如上所述的温室中并通过地下灌溉浇水,以防止测试化合物冲走。在20–22d后,目测确定与对照植物相比测试植物的状况,并且按照0至100%的等级评分,其中0对应于无损伤,并且100对应于完全杀死。将目测确定的测试植物的状况与对照植物的状况相比,并且按照0至100%的等级评分,其中0对应于无损伤,并且100对应于完全杀死。
以表中指示的间隔目测评价杂草控制(作为目测控制百分比(%))。所报告的值是平均值。表格中后跟相同字母的平均值没有显著差异(P=0.5,邓肯新MRT)。数据汇总于表1。
实施例7:加拿大田间试验中苗后除草的评价
在加拿大建立了田间试验(在艾伯塔省(Alberta)的艾勒斯利市(Ellerslie);艾伯塔省的尼斯库市(Nisku)和萨斯喀彻温省(Saskatchewan)的汉利市(Hanley)),以评价化合物5、化合物6和化合物7的功效。试验被设计为随机化完整区组,重复四次。在具有天然杂草群体的春小麦中建立了试验,样地尺寸为2-3米(m)x8-10m(宽度x长度)。作物使用常规栽培技术进行施肥、播种和养护,以确保作物的良好生长。
所有除草剂处理均在苗后施用,并在BBCH(植物的物候学发育阶段)14至22生长期施用于作物。除草剂使用背包式或自行车喷雾器施用,其中使用二氧化碳(CO2)作为推进剂。喷雾器使用平坦扇形进气喷嘴,所述喷嘴经校准以递送均匀的喷雾式样,使用100L/ha的喷雾体积提供叶的完全覆盖。所有处理均利用1.25%v/v的甲基化种子油(MSO)施用。与未经处理的对照样地相比,在施用后的几个间隔目测评估对杂草的植物毒性,作为总体控制百分比。通常,每种处理均评估四次重复。所有处理结果均为四次重复的平均值。
除草剂处理
化合物5、化合物6和化合物7分别以100g ae/L EC的乳油(EC)制剂形式施用。
结果在表2至表4中给出。
实施例8:西班牙和德国田间试验中苗后除草的评价
在西班牙(巴尼亚雷斯市(Banares)和格拉尼翁(Granon))和德国(比勒费尔德市(Bielefeld))建立了田间试验,以评价化合物5、化合物6和化合物7的功效。试验被设计为随机化完整区组,重复三至四次。在具有天然杂草群体的冬小麦中建立了试验,样地尺寸为2-2.5米(m)x6-8m(宽度x长度)。作物使用常规栽培技术进行施肥、播种和养护,以确保作物的良好生长。
所有除草剂处理均在苗后施用,并在BBCH 21至23生长期施用于作物。除草剂使用背包式或自行车喷雾器施用,其中使用空气作为推进剂。喷雾器使用平坦扇形进气喷嘴,所述喷嘴经校准以递送均匀的喷雾式样,使用200L/ha的喷雾体积提供叶的完全覆盖。所有处理均利用1.25%v/v的甲基化种子油(MSO)施用。与未经处理的对照样地相比,在施用后的几个间隔目测评估对杂草的植物毒性,作为总体控制百分比。通常,每种处理均评估三至四次重复。所有处理结果均为三或四次重复的平均值。
除草剂处理
化合物5、化合物6和化合物7分别以100g ae/L EC的乳油(EC)制剂形式施用。
结果在表5至表8中给出。
表1至表8中使用以下缩写:
化合物5=4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸丙-2-炔-1-基酯
化合物6=4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸氰甲酯
化合物7=4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸苄基酯
ANTAR=田春黄菊(Anthemis arvensis)(field chamomile)
CENCY=矢车菊(Centaurea cyanus)(cornflower)
CHEAL=藜草(Chenopodium album L.)(普通灰菜)
CIRAR=丝路蓟(Cirsium arvense(L.)Scop.)(加拿大蓟(Canada thistle))
FUMOF=球果紫菫(Fumaria officinalis)(common fumitory)
KCHSC=地肤(Kochia scoparia(L.)Schrad.)(kochia)
MATCH=德国洋甘菊(Matricaria recutita L.)(野生洋甘菊(wild chamomile))
MATIN=新疆三肋果(Matricaria inodora)(scentless mayweed)
PAPRH=虞美人(Papaver rhoeas L.)(普通罂粟)
Res-PAPRH=对苯磺隆和噻吩磺隆(ALS–乙酰乳酸合酶的作用方式)和2,4-D具有抗性的虞美人(Papaver rhoeas L.(普通罂粟))
POLCO=卷茎蓼(Polygonum convolvulus L.)(野生荞麦(wild buckwheat))
SINAR=欧白芥(Sinapis arvensis L.)(野生芥菜)
STEME=繁缕(Stellaria media(L.)Vill.)(普通繁缕)
VERHE=睫毛婆婆纳(Veronica hederifolia)(ivyleaved speedwell)
VERSS=婆婆纳属物种(Veronica spp)(婆婆纳(speedwell))
g ae/ha=克酸当量每公顷
LSD=最小显著差异
DAAA=施用A后的天数
表1:温室条件下除草剂化合物对关键杂草的目测控制百分比(%)
表2:在加拿大萨斯喀彻温省汉利市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 66天后(66DAAA))
表3:在加拿大艾伯塔省尼斯库市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 28-51天后(28-51DAAA))
表4:在加拿大艾伯塔省艾勒斯利市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 51天后(51DAAA))
表5:在西班牙格拉尼翁市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 34-84天后(34-84DAAA))
表6:在西班牙巴尼亚雷斯市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 66-83天后(66-83DAAA))
表7:在西班牙格拉尼翁市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 48-68天后(48-68DAAA))
表8:在德国比勒费尔德市的田间条件下,除草剂化合物对关键杂草的目测控制百分比(%)(在施用A 85天后(85DAAA))
从上述结果可以看出,本发明的式(I)的化合物具有除草活性。从上述结果还可以看出,化合物5和化合物6表现出优于化合物7的除草活性。这些新的化学除草剂提供了更光谱的杂草控制、更高的除杂草活性,并提供了解决对传统上用于控制它们的除草剂产生了抗性的杂草的管理的方法。
尽管已经将本公开描述为具有示例性方面或实施方案,但是可在本公开的精神和范围内进一步修改本公开。本申请因而旨在涵盖使用本公开一般原理的任何变化、用途或修改。此外,本申请旨在涵盖落在本公开所属领域中的已知或常规实践范围内的本公开的此类偏离。
益处、优点、问题的解决方案以及可导致任何益处,优点或解决方案出现或变得更加明显的任何要素都不应解释为关键、要求或必要的特征或要素。因此,范围仅受所附权利要求书的限制,在所附权利要求书中,除非明确地这样陈述,否则提及单数形式的元件并非旨在表示“一个且只有一个”,而是“一个或多个”。此外,在权利要求中使用类似于“A、B或C中的至少一个”的短语时,旨在将该短语解释为意指在一个实施方案中可单独存在A,在一个实施方案中可单独存在B,在一个实施方案中可单独存在C,或在单个实施方案中可存在元素A、B或C的任何组合;例如,A和B、A和C、B和C、或A和B和C。
在本文的详细描述中,对“一个实施方案”、“实施方案”,“示例性实施方案”等的提及指示所描述的实施方案可包括特定的特征、结构或特性,但是每个实施方案可不必包括特定的特征、结构或特性。此外,这样的短语不必须指代相同的实施方案。此外,当结合实施方案描述特定的特征、结构或特性时,认为结合其他实施方案利用本公开的益处影响这种特征、结构或特性在本领域技术人员的认识之内,无论是否明确描述。
Claims (12)
2.如权利要求1所述的化合物,其中
X为CF、CCl或CBr;并且
R2为氯;
或其N-氧化物或农业上可接受的盐。
3.如权利要求1所述的化合物,其中X为CF。
4.如权利要求3所述的化合物,其中R2为Cl。
5.如权利要求3所述的化合物,其中R5为F。
6.如权利要求4所述的化合物,其中R5为F。
7.如权利要求6所述的化合物,其中所述化合物为4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶甲酸氰甲酯。
8.一种除草剂组合物,其包含如权利要求1所述的化合物和农业上可接受的佐剂或载剂。
9.如权利要求8所述的组合物,其还包含至少一种另外的除草剂化合物。
10.如权利要求8所述的组合物,其还包含安全剂。
11.一种用于控制不期望植被的方法,包括:
提供如权利要求1所述的化合物;以及
将所述化合物施用于不期望植被或其所在地。
12.一种用于控制不期望植被的方法,包括:
提供如权利要求9所述的组合物;以及
将所述组合物施用于不期望植被或其所在地。
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WO2019046667A1 (en) * | 2017-09-01 | 2019-03-07 | Dow Agrosciences Llc | HERBICIDAL COMPOSITIONS CONTAINING PYRIDINE CARBOXYLIC ACIDS OR DERIVATIVES THEREOF, WITH INHIBITORS OF PDS AND VLCFA, OR DERIVATIVES THEREOF |
EP3675635A4 (en) * | 2017-09-01 | 2021-05-19 | Dow Agrosciences LLC | HERBICIDAL COMPOSITIONS WITH PYRIDINCARBONIC ACID OR DERIVATIVES THEREOF, WITH GLYPHOSATE OR GLUFOSINATE OR DERIVATIVES THEREOF |
EP3876726A1 (en) * | 2018-11-06 | 2021-09-15 | Corteva Agriscience LLC | Compositions comprising pyridine carboxylate herbicides and azole carboxylate safeners |
WO2020096833A1 (en) * | 2018-11-06 | 2020-05-14 | Dow Agrosciences Llc | Safened compositions comprising pyridine carboxylate herbicides and isoxadifen |
US20210400968A1 (en) * | 2018-11-06 | 2021-12-30 | Corteva Agriscience Llc | Safened compositions comprising pyridine carboxylate herbicides and cloquintocet |
AU2019374751A1 (en) * | 2018-11-07 | 2021-05-20 | Corteva Agriscience Llc | Compositions comprising pyridine carboxylate herbicides with PDS inhibitor herbicides |
BR112021008822A2 (pt) * | 2018-11-07 | 2021-08-17 | Corteva Agriscience Llc | composições que compreendem herbicidas de carboxilato de piridina com glifosato ou glufosinato |
MA54165A (fr) * | 2018-11-07 | 2022-02-16 | Corteva Agriscience Llc | Compositions comprenant un herbicide à base de carboxylate de pyridine et des herbicides à base d'inhibiteurs de la protoporphyrinogène oxydase (protox) |
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EA202191258A1 (ru) * | 2018-11-07 | 2021-09-22 | КОРТЕВА АГРИСАЙЕНС ЭлЭлСи | Композиции, содержащие гербициды на основе пиридинкарбоксилата с гербицидами на основе ингибитора ацетолактатсинтазы (als) |
EA202191268A1 (ru) * | 2018-11-07 | 2021-07-26 | КОРТЕВА АГРИСАЙЕНС ЭлЭлСи | Композиции, содержащие гербицид на основе пиридинкарбоксилата и гербицид, представляющий собой ингибитор сборки микротрубочек |
CA3118579A1 (en) * | 2018-11-07 | 2020-05-14 | Corteva Agriscience Llc | Compositions comprising pyridine carboxylate herbicides and cellulose biosynthesis inhibitor herbicides |
WO2020096924A1 (en) * | 2018-11-07 | 2020-05-14 | Dow Agrosciences Llc | Compositions comprising pyridine carboxylate herbicides and very long chain fatty acid (vlcfa) synthesis inhibitor herbicides |
EP3876725A1 (en) * | 2018-11-07 | 2021-09-15 | Corteva Agriscience LLC | Compositions comprising pyridine carboxylate herbicides and fatty acid and lipid synthesis inhibitor herbicides |
EA202191272A1 (ru) * | 2018-11-07 | 2021-08-12 | КОРТЕВА АГРИСАЙЕНС ЭлЭлСи | КОМПОЗИЦИИ, СОДЕРЖАЩИЕ ГЕРБИЦИДЫ НА ОСНОВЕ ПИРИДИНКАРБОКСИЛАТА И ГЕРБИЦИДЫ, ПРЕДСТАВЛЯЮЩИЕ СОБОЙ ИНГИБИТОРЫ АЦЕТИЛ-CoA-КАРБОКСИЛАЗЫ (ACCазы) |
CA3118670A1 (en) * | 2018-11-07 | 2020-05-14 | Corteva Agriscience Llc | Compositions comprising pyridine carboxylate herbicides and plant growth regulators |
EP3876727A1 (en) * | 2018-11-07 | 2021-09-15 | Corteva Agriscience LLC | Compositions comprising pyridine carboxylate herbicides with synthetic auxin herbicides or auxin transport inhibitors |
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WO2021144264A1 (en) * | 2020-01-16 | 2021-07-22 | Bayer Aktiengesellschaft | Crystalline form of the herbicide methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1h-indol-6-yl)picolinate |
EP4121414A1 (en) | 2020-03-18 | 2023-01-25 | Corteva Agriscience LLC | Improved synthesis of 4-amino-6-(heterocyclic)picolinates |
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