CN116457349A - 除草n-杂芳基吡唑化合物 - Google Patents
除草n-杂芳基吡唑化合物 Download PDFInfo
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- CN116457349A CN116457349A CN202180076109.1A CN202180076109A CN116457349A CN 116457349 A CN116457349 A CN 116457349A CN 202180076109 A CN202180076109 A CN 202180076109A CN 116457349 A CN116457349 A CN 116457349A
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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
- C07D401/14—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 three or more hetero rings
-
- 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
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
-
- 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
- A01P13/02—Herbicides; Algicides selective
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及具有式(I)的化合物或所述化合物的农艺学上可接受的盐，其中A1、A2、A3、Q、X、R1和R2是如本文中所定义的。本发明进一步涉及包含具有式(I)的化合物的除草组合物以及具有式(I)的化合物用于控制特别是在有用植物的作物中的杂草的用途。
Description
本发明涉及除草化合物、其制备方法、包含这些新的化合物的除草组合物、以及其用于控制杂草(特别是在有用植物作物中)的用途或用于抑制植物生长的用途。
吡唑基嘧啶醚化合物披露于例如CN 107540664中。本发明涉及除草吡唑基嘧啶化合物。
因此，根据本发明，提供了一种具有式(I)的化合物：
或其农艺学上可接受的盐，
其中
A1、A2和A3独立地为CH或N，其前提是A1、A2和A3中不超过一个是N；
X选自由以下组成的组：O、S和CH2；
Q是6元含氮杂芳基，其任选地被一个或多个R3取代；
R1选自由以下组成的组：C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基；
R2选自由以下组成的组：C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、卤素、C1-C4烷氧基、-S-C1-C4烷基和-S-C1-C4卤代烷基；
R3选自由以下组成的组：卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、-CN、NO2、C2-C4烯基、C2-C4炔基、-S(O)pC1-C4烷基；并且
p＝0、1或2。
C1-C4烷基-包括例如甲基(Me，CH3)、乙基(Et，C2H5)、正丙基(n-Pr)、异丙基(i-Pr)、正丁基(n-Bu)、异丁基(i-Bu)、仲丁基和叔丁基(t-Bu)。C1-C2烷基是甲基(Me，CH3)或乙基(Et，C2H5)。
卤素(或卤代)包括例如氟、氯、溴或碘。上述情况对应地适用于其他定义背景下的卤素，如卤代烷基。
C1-C4卤代烷基-和C1-C2卤代烷基包括例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、或1,1-二氟-2,2,2-三氯乙基。
C1-C4烷氧基和C1-C2烷氧基包括例如甲氧基和乙氧基。
C1-C4卤代烷氧基-包括例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基或2,2,2-三氯乙氧基，优选地二氟甲氧基、2-氯乙氧基或三氟甲氧基。
C2-C4烯基-包括例如-CH＝CH2(乙烯基)和-CH2-CH＝CH2(烯丙基)。
C2-C4炔基-是指仅由碳原子和氢原子组成的直链或支链的烃链基团，该烃链基团含有至少一个三键，具有从二至四个碳原子，并且通过单键附接至分子的其余部分。C2-C4炔基的实例包括但不限于丙-1-炔基、炔丙基(丙-2-炔基)和丁-1-炔基。
C1-C4烷基-S-(烷硫基)包括例如甲硫基、乙硫基、丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基，优选甲硫基或乙硫基。
C1-C4烷基-S(O)-(烷基亚磺酰基)包括例如甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基或叔丁基亚磺酰基，优选甲基亚磺酰基或乙基亚磺酰基。
C1-C4烷基-S(O)2-(烷基磺酰基)包括例如甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基或叔丁基磺酰基，优选甲基磺酰基或乙基磺酰基。
在本发明的优选的实施例中，提供了一种具有式(I)的化合物，其中X是O。
在本发明的一个实施例中，提供了一种具有式(I)的化合物，其中A1、A2和A3均为CH。在另一个实施例中，提供了一种具有式(I)的化合物，其中A1是N，A2是CH并且A3是CH。在另一个实施例中，提供了一种具有式(I)的化合物，其中A1是CH，A2是N并且A3是CH。在另一个实施例中，提供了一种具有式(I)的化合物，其中A1是CH，A2是CH并且A3是N。在本发明的优选的实施例中，A1是CH、A2是CH并且A3是CH或N。
在本发明的另一个实施例中，提供了一种具有式(I)的化合物，其中Q选自由以下组成的组：
其中n是0、1或2。
在其中n是1或2的实施例中，每个R3独立地选自由以下组成的组：卤素、C1-C4烷基(优选C1-C2烷基)、C1-C4卤代烷基(优选C1-C2卤代烷基)、C1-C4烷氧基(优选C1-C2烷氧基-)、C1-C4卤代烷氧基、-CN、NO2、C2-C4烯基、C2-C4炔基、-S(O)pC1-C4烷基。在优选的实施例中，R3是卤素。
在本发明的优选的实施例中，提供了一种具有式(I)的化合物，其中Q是Q2或Q5、并且尤其是Q5。在更优选的实施例中，Q是Q5，并且n是1，并且R3优选地是卤素。
在本发明的另一个优选的实施例中，提供了一种具有式(I)的化合物，其中R1是C1-C4卤代烷基(优选C1-C2卤代烷基)、更优选CF3。
在本发明的另一个优选的实施例中，提供了一种具有式(I)的化合物，其中R2选自由以下组成的组：卤素、C1-C4卤代烷基(优选C1-C2卤代烷基(例如CF2H或CF3))以及C1-C4卤代烷氧基(例如-OCF2H、-OCF3)。
在本发明的优选的实施例中，提供了一种具有式(I)的化合物，其中X＝O，A1是CH，A2是CH，A3是CH或N，Q是Q2或Q5(优选Q5)，R1是C1-C4卤代烷基并且R2选自由以下组成的组：卤素、C1-C4卤代烷基(优选C1-C2卤代烷基(例如CF2H或CF3))以及C1-C4卤代烷氧基(例如-OCF2H、-OCF3)。
具有式(I)的化合物可以含有不对称中心并且可以作为单一对映异构体、以任何比例的对映异构体对而存在，或者在存在多于一个不对称中心的情况下，含有所有可能比率的非对映异构体。典型地，与其他可能性相比，这些对映异构体之一具有增强的生物活性。
本发明还提供了具有式(I)的化合物的农艺学上可接受的盐。优选的是具有式(I)的化合物可以与以下形成的盐：胺，包括伯胺、仲胺和叔胺(例如氨、二甲胺和三乙胺)，碱金属碱和碱土金属碱，过渡金属碱或季铵碱。
根据本发明的具有式(I)的化合物可以自身被用作除草剂，但是通常使用配制辅助剂(如载体、溶剂和表面活性剂(SAA))将它们配制成除草组合物。因此，本发明进一步提供了一种除草组合物，该除草组合物包含根据前述权利要求中任一项所述的除草化合物和农业上可接受的配制辅助剂。组合物可以呈浓缩物的形式，在使用前稀释这些浓缩物，尽管也可以制成即用型组合物。最终稀释通常用水进行，但是可以替代水或除了水之外使用例如液体肥料、微量营养素、生物有机体、油或溶剂进行。
除草组合物总体上包含按重量计从0.1％至99％、尤其是按重量计从0.1％至95％的具有式I的化合物和按重量计从1％至99.9％的配制辅助剂，该配制辅助剂优选地包括按重量计从0至25％的表面活性物质。
组合物可以选自许多配制品类型。这些包括乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬乳液(SE)、胶囊悬浮液(CS)、水可分散性颗粒剂(WG)、可乳化性颗粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散剂(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮液(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可溶性粉剂(SP)、可湿性粉剂(WP)以及可溶性颗粒剂(SG)。在任何情况下，所选择的配制品类型将取决于所设想的具体目的以及具有式(I)的化合物的物理、化学和生物特性。
可溶性粉剂(SP)可以通过以下方式制备：将具有式(I)的化合物与一种或多种水溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选地一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物进行混合，以改进水分散性/水溶性。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过将具有式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地，一种或多种分散剂，以及任选地，一种或多种悬浮剂混合来制备以促进在液体中的分散。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
可以这样形成颗粒剂(GR)：通过将具有式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物颗粒化形成，或者通过将具有式(I)的化合物(或其在合适试剂中的溶液)吸收进多孔颗粒材料(如浮石、凹凸棒石粘土、漂白土、硅藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉)，或通过将具有式(I)的化合物(或其在合适试剂中的溶液)吸附到硬芯材料(如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话，进行干燥来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。一种或多种其他添加剂也可以包含在颗粒剂中(例如乳化剂、湿润剂或分散剂)。
可分散性浓缩物(DC)可以通过将具有式(I)的化合物溶于水或有机溶剂(如酮、醇或二醇醚)中来制备。这些溶液可以含有表面活性剂(例如以改善水稀释或防止喷雾罐中的结晶)。
可乳化性浓缩物(EC)或水包油乳液(EW)可以通过将具有式(I)的化合物溶于有机溶剂(任选地含有一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的合适有机溶剂包括芳香族烃(如烷基苯或烷基萘，以SOLVESSO 100、SOLVESSO 150和SOLVESSO 200为例；SOLVESSO是注册商标)、酮(如环己酮或甲基环己酮)和醇(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃。EC产品可以在添加到水中时自发地乳化，从而产生具有足够稳定性的乳液，以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体，则它可以在典型地低于70℃的合适温度下熔化)或处于溶液中(通过将它溶于适当的溶剂中)的具有式(I)的化合物，并且然后在高剪切下将所得液体或溶液乳化进含有一种或多种SAA的水中，以产生乳液。在EW中使用的合适溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及在水中具有低溶解度的其他适当的有机溶剂。
微乳液(ME)可以通过将水与一种或多种溶剂和一种或多种SAA的共混物混合来制备，以自发地产生热力学稳定的各向同性的液体配制品。具有式(I)的化合物最初就存在于水中或溶剂/SAA共混物中。在ME中使用的合适溶剂包括上文描述的在EC或EW中使用的那些。ME可以是水包油体系或油包水体系(存在哪种体系可以通过电导率测量来测定)并且可以适用于在同一配制品中混合水溶性的杀有害生物剂和油溶性的杀有害生物剂。ME适用于稀释到水中，保持为微乳液或形成常规的水包油乳液。
悬浮液浓缩物(SC)可以包括具有式(I)的化合物的精细分散的不溶固体颗粒的水性或非水性悬浮液。SC可以通过将具有式(I)的固体化合物任选地与一种或多种分散剂在合适的介质中球磨或珠磨来制备，以产生该化合物的细颗粒悬浮液。在组合物中可以包含一种或多种湿润剂，并且可以包含悬浮剂以降低颗粒沉降的速率。可替代地，可以干磨具有式(I)的化合物并且将其添加到含有上文描述的试剂的水中，以产生期望的最终产物。
气溶胶配制品包含具有式(I)的化合物和合适的推进剂(例如正丁烷)。还可以将具有式(I)的化合物溶于或分散于合适的介质(例如水或可与水混溶的液体，如正丙醇)中以提供在不加压的手动喷洒泵中使用的组合物。
胶囊悬浮液(CS)可以通过与制备EW配制品类似的方式来制备，但具有另外的聚合阶段，使得获得油滴的水性分散体，其中每个油滴被聚合物壳所包裹并且含有具有式(I)的化合物以及任选地用于该油滴的载体或稀释剂。聚合物壳可以通过界面缩聚反应或通过凝聚程序产生。这些组合物可以提供具有式(I)的化合物的受控释放并且它们可以用于种子处理。具有式(I)的化合物还可以配制在可生物降解的聚合物基质中以提供该化合物的缓慢的、受控的释放。
组合物可以包含一种或多种添加剂以改进该组合物的生物性能，例如通过改进在表面上的湿润性、保持力或分布；被处理表面上的抗雨水性；或具有式(I)的化合物的吸收或流动。此类添加剂包括表面活性剂(SAA)，基于油的喷洒添加剂，例如某些矿物油或天然植物油(如大豆和菜籽油)，改性的植物油(如甲基化菜籽油(MRSO))，以及这些与其他生物增强辅助剂(可以帮助或改变具有式(I)的化合物的作用的成分)的共混物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非离子类型的SAA。
合适的阳离子类型的SAA包括季铵化合物(例如鲸蜡三甲基溴化铵)、咪唑啉以及胺盐。
合适的阴离子SAA包括脂肪酸的碱金属盐、硫酸的脂肪族单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物，例如月桂醇与四磷酸之间的反应；另外这些产物可以被乙氧基化)、磺基琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐、木质磺酸盐以及三苯乙烯基酚的磷酸盐/硫酸盐。
合适的两性类型的SAA包括甜菜碱、丙酸盐和甘氨酸盐。
合适的非离子类型的SAA包括环氧烷(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇(如油醇或鲸蜡醇)或与烷基酚(如辛基酚、壬基酚或辛基甲酚)的缩合产物；衍生自长链脂肪酸或己糖醇酐的偏酯；所述偏酯与环氧乙烷的缩合产物；嵌段聚合物(包含环氧乙烷和环氧丙烷)；烷醇酰胺；单酯(例如脂肪酸聚乙二醇酯)；胺氧化物(例如月桂基二甲基氧化胺)；卵磷脂和脱水山梨糖醇及其酯，烷基多糖苷和三苯乙烯基酚。
合适的悬浮剂包括亲水性胶体(如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(如膨润土或凹凸棒石)。
本发明的化合物还可以与一种或多种另外的除草剂和/或植物生长调节剂混合使用。此类另外的除草剂或植物生长调节剂的实例包括乙草胺、三氟羧草醚(包括三氟羧草醚-钠)、苯草醚、莠灭净、氨唑草酮、氯氨吡啶酸、杀草强、莠去津、氟丁酰草胺-M、喹草酮、苄嘧磺隆(包括苄嘧磺隆-甲基)、灭草松、双环吡喃酮、双丙氨膦、双草醚-钠、比克罗腙(bixlozone)、除草定、溴苯腈、丁草胺、氟丙嘧草酯、唑草酮(包括唑草酮-乙基)、氯酯磺草胺(包括氯酯磺草胺-甲基)、氯嘧磺隆(包括氯嘧磺隆-乙基)、绿麦隆、氯磺隆、环庚草醚、氯酰草膦(clacyfos)、烯草酮、炔草酸(包括炔草酯)、异噁草酮、二氯吡啶酸、环吡拉尼(cyclopyranil)、环吡瑞莫(cyclopyrimorate)、环丙嘧磺隆、氰氟草酯(包括氰氟草酯-丁基)、2,4-D(包括其胆碱盐和2-乙基己基酯)、2,4-DB、敌菜安、麦草畏(包括其铝、氨基丙基、双-氨基丙基甲基、胆碱、二氯丙、二甘醇胺、二甲胺、二甲基铵、钾盐和钠盐)、双氯磺草胺、吡氟酰草胺、氟吡草腙、二甲草胺、精二甲吩草胺、二溴敌草快、敌草隆、苯吡菌胺(epyrifenacil)、乙丁烯氟灵、乙氧呋草黄、噁唑禾草灵(包括精噁唑禾草灵-乙基)、苯磺噁唑草(fenoxasulfone)、芬奎崔顿(fenquinotrione)、四唑酰草胺、啶嘧磺隆、双氟磺草胺、氯氟吡啶酯(florpyrauxifen)(包括氯氟吡啶酯-苄基)、吡氟禾草灵(包括精吡氟禾草灵-丁基)、氟酮磺隆(包括氟酮磺隆-钠)、氟噻草胺、唑嘧磺草胺、丙炔氟草胺、氟草隆、氟啶嘧磺隆(包括氟啶嘧磺隆-甲基-钠)、氟草烟(包括氯氟吡氧乙酸(fluroxypyr-meptyl))、氟黄胺草醚、甲酰胺磺隆、草铵膦(包括L-草铵膦和两者的铵盐)、草甘膦(包括其联胺、异丙基铵和钾盐)、氟氯吡啶酯(halauxifen)(包括氟氯吡啶酯-甲基)、氟吡甲禾灵(包括氟吡甲禾灵-甲基)、环嗪酮、乙内酰脲啶(hydantocidin)、甲氧咪草烟、甲咪唑烟酸、灭草烟、咪草烟、茚嗪氟草胺、碘甲磺隆(包括碘甲磺隆-甲基-钠)、碘芬磺隆(iofensulfuron)(包括碘芬磺隆-钠)、碘苯腈、异丙隆、异噁唑草酮、兰柯三酮(lancotrione)、MCPA、MCPB、高2-甲-4-氯丙酸(mecoprop-P)、甲基二磺隆(包括甲基二磺隆-甲基)、甲基磺草酮、苯嗪草酮、吡草胺、异噁噻草醚(methiozolin)、异丙甲草胺、磺草唑胺、嗪草酮、甲磺隆、敌草胺、烟嘧磺隆、达草灭、噁草酮、环氧嘧磺隆、乙氧氟草醚、二氯化百草枯、二甲戊乐灵、五氟磺草胺、苯敌草、毒莠定、唑啉草酯、丙草胺、氟嘧磺隆-甲基、扑草净、敌稗、喔草酯、丙嗪嘧磺隆(propyrisulfuron)、戊炔草胺、苄草丹、氟磺隆、双唑草腈、吡草醚(pyraflufen)(包括吡草醚-乙基)、磺酰草吡唑、哒草特、环酯草醚、嘧氟磺草胺(pyrimisulfan)、吡咯磺隆(pyroxasulfone)、啶磺草胺、二氯喹啉酸、氯甲喹啉酸、喹禾灵(包括精喹禾灵-乙基和喹禾糠酯(quizalofop-P-tefuryl))、砜嘧磺隆、嘧啶肟草醚、烯禾啶、西玛津、精异丙甲草胺、甲磺草胺、磺酰磺隆、丁噻隆、特呋三酮、环磺酮、特丁津、特丁净、四氟吡咯烷酮(tetflupyrolimet)、噻酮磺隆(thiencarbazone)、噻吩磺隆、氟嘧硫草酯(tiafenacil)、托比利特(tolpyralate)、苯吡唑草酮、三甲苯草酮、氟酮磺草胺(triafamone)、野麦畏、醚苯磺隆、苯磺隆(包括苯磺隆-甲基)、绿草定、三氟啶磺隆(包括三氟啶磺隆-钠)、三氟草嗪(trifludimoxazin)、氟乐灵、氟胺磺隆、3-(2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢嘧啶-1(2H)-基)苯基)-5-甲基-4,5-二氢异噁唑-5-甲酸乙酯、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑啉-2-酮、(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑啉-2-酮、3-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]双环[3.2.1]辛烷-2,4-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮、6-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-乙基-环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-4,4,6,6-四甲基-环己烷-1,3-二酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮、3-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]双环[3.2.1]辛烷-2,4-二酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮、6-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮、4-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮、4-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸(包括其农用化学上可接受的酯，例如，4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸甲酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸丙-2-炔基酯和4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸氰基甲酯)、3-乙基硫烷基-N-(1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、3-(异丙基硫烷基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、3-(异丙基磺酰基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、3-(乙基磺酰基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、2-[[3-[[3-氯-5-氟-6-[3-甲基-2,6-二氧代-4-(三氟甲基)嘧啶-1-基]-2-吡啶基]氧基]乙酸乙酯、6-氯-4-(2,7-二甲基-1-萘基)-5-羟基-2-甲基-哒嗪-3-酮、1-[2-氯-6-(5-氯嘧啶-2-基)氧基-苯基]-4,4,4-三氟-丁-1-酮和5-[2-氯-6-(5-氯嘧啶-2-基)氧基-苯基]-3-(二氟甲基)异噁唑。
具有式(I)的化合物的混合配伍物还可以呈酯或盐的形式，如例如在ThePesticide Manual[杀有害生物剂手册],第十六版,英国作物保护委员会(British CropProtection Council),2012中所提到的。
具有式(I)的化合物还可以与其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)混合使用，其实例在The Pesticide Manual[杀有害生物剂手册]中给出。
具有式(I)的化合物与混合配伍物的混合比优选地是从1:100至1000:1。
这些混合物可以有利地用于以上提到的配制品中(在这种情况下“活性成分”涉及具有式(I)的化合物与混合配伍物的相应混合物)。
本发明的化合物或混合物还可以与一种或多种除草剂安全剂组合使用。此类安全剂的实例包括解草嗪、解草酯(cloquintocet)(包括解毒喹)、环丙磺酰胺、二氯丙烯胺、解草唑(包括解草唑-乙基)、解草啶、氟草肟、解草噁唑、双苯噁唑酸(包括双苯噁唑酸-乙基)、吡唑解草酸(mefenpyr)(包括吡唑解草酸-二乙基)、metcamifen和解草腈。
特别优选的是具有式(I)的化合物与环丙磺酰胺、双苯噁唑酸乙酯、解毒喹和/或metcamifen的混合物。
具有式(I)的化合物的安全剂还可以呈酯或盐的形式，如例如在The PesticideManual[杀有害生物剂手册],第16版(BCPC),2012中所提到的。对解毒喹的提及还适用于其锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或鏻盐(如在WO 02/34048中披露的)。
优选地，具有式(I)的化合物与安全剂的混合比是从100:1至1:10，尤其是从20:1至1:1。
本发明还进一步提供了一种在场所处控制杂草的方法，所述方法包括向所述场所施用控制杂草量的包含具有式(I)的化合物的组合物。此外，本发明可以进一步提供一种在包括作物植物和杂草的场所处选择性地控制杂草的方法，其中该方法包括向该场所施用控制杂草量的根据本发明的组合物。‘控制’意指杀死、减少或延迟生长或防止或减少发芽。应指出，与已知的结构类似的化合物相比，本发明的化合物示出很大改善的选择性。通常有待控制的植物是不想要的植物(杂草)。‘场所’意指植物在其中正生长或将生长的区域。施用可以在作物植物的出苗前和/或出苗后施用至场所。一些作物植物可以固有地耐受具有式(I)的化合物的除草作用。优选的作物植物包括玉米、小麦、大麦和水稻。
具有式I的化合物的施用比率可以在宽极限内变化并且取决于土壤的性质、施用方法(出苗前或出苗后；种子拌种；施用于种子沟；免耕法施用等)、作物植物、待控制的一种或多种杂草、当时的气候条件和其他受施用方法、施用时间和目标作物支配的因素。根据本发明的具有式I的化合物通常以从10g/ha至2500g/ha，尤其是从25g/ha至1000g/ha，更尤其是从25g/ha至250g/ha的比率施用。
通常通过喷洒该组合物进行施用，典型地是通过用于大面积的装在拖拉机上的喷洒机，但是还可以使用其他方法如撒粉(针对粉末)、滴加或浸灌。
作物植物应理解为还包括通过常规的育种方法或通过基因工程已经赋予对其他除草剂或多种类别的除草剂(例如ALS-抑制剂、GS-抑制剂、EPSPS-抑制剂、PPO-抑制剂、HPPD-抑制剂、抑制剂-PDS以及ACC酶-抑制剂)的耐受性的那些作物植物。通过常规的育种方法已经赋予对咪唑啉酮(例如，甲氧咪草烟)的耐受性的作物的实例是夏季油菜(卡诺拉(canola))。通过基因工程方法已经赋予对除草剂的耐受性的作物的实例包括例如具有草甘膦和草铵膦抗性的玉米品种，这些玉米品种在/>和商标名下是可商购的。还可以将本发明的化合物与WO 2020/236790中所披露的植物联合使用。
作物植物还应理解为通过基因工程方法已经赋予对有害昆虫的抗性的那些，例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性)。Bt玉米的实例是的Bt 176玉米杂交体(先正达种子公司(Syngenta Seeds))。Bt毒素是由苏芸金芽孢杆菌(Bacillus thuringiensis)土壤细菌天然形成的蛋白质。毒素或能够合成此类毒素的转基因植物的实例被描述在EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包含一个或多个编码杀昆虫抗性和表达一种或多种毒素的基因的转基因植物的实例是(玉米)、Yield/>(玉米)、/>(棉花)、(棉花)、/>(马铃薯)、/>以及/>植物作物或其种子材料均可以是抗除草剂的并且同时是抗昆虫摄食的(“叠加的”转基因事件)。例如，种子可以具有表达杀昆虫的Cry3蛋白的能力，而同时对草甘膦是耐受的。
作物植物还应理解为包括通过常规的育种或基因工程的方法获得并且包含所谓的输出性状(例如改进的储存稳定性、更高的营养价值以及改进的风味)的那些。
可以使用这些组合物来控制不想要的植物(统称为‘杂草’)。有待控制的杂草既可以是单子叶物种，例如剪股颖属(Agrostis)、看麦娘属(Alopecurus)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、莎草属(Cyperus)、马唐属(Digitaria)、稗属(Echinochloa)、穇属(Eleusine)、黑麦草属(Lolium)、雨久花属(Monochoria)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、藨草属(Scirpus)、狗尾草属(Setaria)以及高粱属(Sorghum)，也可以是双子叶物种，例如苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、藜属(Chenopodium)、菊属(Chrysanthemum)、白酒草属(Conyza)、拉拉藤属(Galium)、番薯属(Ipomoea)、旱金莲属(Nasturtium)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、繁缕属(Stellaria)、婆婆纳属(Veronica)、堇菜属(Viola)以及苍耳属(Xanthium)。
在本发明的另外的方面，提供了如本文所定义的具有式(I)的化合物作为除草剂的用途。
用于制备具有式(I)的化合物的方法
用于制备化合物(例如具有式(I)的化合物(所述化合物任选地可以是其农业化学上可接受的盐))的方法现在加以描述，并且形成本发明的另外的方面。
具有式I的化合物可以由具有式A的化合物通过与具有式B的化合物(其中LG表示合适的离去基团，如Br或Cl)在合适的碱的存在下并且任选地在合适的催化剂/配体组合的存在下并且在合适的溶剂中的反应来制备。合适的碱可以包括Cs2CO3。合适的催化剂/配体组合可以包括Cu(I)I/1,10-菲咯啉。合适的溶剂可以包括DMSO。
具有式A的化合物可以由具有式C的化合物通过与具有式D的化合物(其中LG表示合适的离去基团，如Br或Cl)在合适的碱的存在下并且任选地在合适的催化剂/配体组合的存在下并且在合适的溶剂中的反应来制备。合适的碱可以包括Cs2CO3。合适的催化剂/配体组合可以包括Cu(I)I/1,10-菲咯啉。合适的溶剂可以包括DMSO。
在可替代的方法中，具有式I的化合物可以由具有式E的化合物通过与具有式D的化合物(其中LG表示合适的离去基团，如Br或Cl)在合适的碱的存在下并且任选地在合适的催化剂/配体组合的存在下并且在合适的溶剂中的反应来制备。合适的碱可以包括Cs2CO3。合适的催化剂/配体组合可以包括Cu(I)I/1,10-菲咯啉。合适的溶剂可以包括DMSO。
具有式E的化合物可以由具有式C的化合物通过与具有式B的化合物(其中LG表示合适的离去基团，如Br或Cl)在合适的碱的存在下并且任选地在合适的催化剂/配体组合的存在下并且在合适的溶剂中的反应来制备。合适的碱可以包括Cs2CO3。合适的催化剂/配体组合可以包括Cu(I)I/1,10-菲咯啉。合适的溶剂可以包括DMSO。
以下非限制性实例提供了用于本发明的代表性化合物(如下表1中所提及的)的具体合成方法。
实例1：2-[5-[[6-(二氟甲氧基)-2-吡啶基]氧基]-3-(三氟甲基)吡唑-1-基]-5-氟-嘧啶(化合物1.005)的合成
步骤1：2-[5-[[6-(二氟甲氧基)-2-吡啶基]氧基]-3-(三氟甲基)吡唑-1-基]-5-氟-嘧啶(化合物1.005)的合成
向在N2气氛下的在DMSO(8.1mL)中的3-(三氟甲基)-1H-吡唑-5-醇(0.30g，2.0mmol)的搅拌溶液中加入2-溴-6-(二氟甲氧基)吡啶(0.49g，2.2mmol)、Cu(I)I(0.096g，0.49mmol)、1,10-菲咯啉(0.18g，0.99mmol)以及Cs2CO3(1.90g，5.9mmol)，并且加热至120℃持续18小时。使反应冷却至RT，并且然后加入2-氯-5-氟-嘧啶(0.49mL，3.9mmol)，并且将反应在120℃下加热持续1小时。使反应冷却、过滤，并且然后通过反相质量定向HPLC纯化以得到呈淡粉色固体的所希望的产物(83mg，11％)。
1H NMR(400MHz,CDCl3)δ8.58(s,2H),7.81(t,1H),6.98(t,1H),6.85(d,1H),6.67(d,1H),6.50(s,1H)
表1-本发明的除草化合物的实例。
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生物学实例
将多种测试物种(苘麻(Abutilon theophrasti)(ABUTH)、反枝苋(Amaranthusretoflexus)(AMARE)、稗草(Echinochloa crus-galli)(ECHCG)、碗仔花(Ipomoeahederacea)(IPOHE)、大狗尾草(Setaria faberi)(SETFA))的种子播种在盆中的标准土壤中。在温室中在受控条件(24℃/16℃，白天/夜晚；14小时光照；65％湿度)下培养一天(出苗前)之后或培养8天(出苗后)之后，用水性喷雾溶液喷洒这些植物，该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品，含有0.5％ Tween 20(聚氧乙烯脱水山梨糖醇单月桂酸酯，CAS RN 9005-64-5)。除非另有说明，否则化合物以250g/ha施用。然后使测试植物在温室中在受控条件下在温室(24℃/16℃，白天/夜晚；14小时光照；65％湿度)下生长，并且每日浇水两次。出苗前和出苗后13天后，对测试给植物造成的损害百分比进行评估。下表中以五分制示出了生物学活性(5＝81％-100％；4＝61％-80％；3＝41％-60％；2＝21％-40％；1＝0％-20％)。
表B1出苗后测试
表B2出苗前测试
NT＝未测试。
Claims (15)
1.一种具有式(I)的化合物：
或其农艺学上可接受的盐，
其中
A1、A2和A3独立地为CH或N，其前提是A1、A2和A3中不超过一个是N；
X选自由以下组成的组：O、S和CH2；
Q是6元含氮杂芳基，其任选地被一个或多个R3取代；
R1选自由以下组成的组：C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基；
R2选自由以下组成的组：C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、卤素、C1-C4烷氧基、-S-C1-C4烷基和-S-C1-C4卤代烷基；
R3选自由以下组成的组：卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、-CN、NO2、C2-C4烯基、C2-C4炔基、-S(O)pC1-C4烷基；并且
p＝0、1或2。
2.根据权利要求1所述的具有式(I)的化合物，其中，X是O。
3.根据权利要求1或权利要求2所述的具有式(I)的化合物，其中，A1、A2和A3均为CH。
4.根据前述权利要求中任一项所述的具有式(I)的化合物，其中，Q选自由以下组成的组：
其中n是0、1或2。
5.根据权利要求4所述的具有式(I)的化合物，其中，Q是Q5。
6.根据权利要求5所述的化合物，其中，n是1或2。
7.根据权利要求6所述的化合物，其中，n是1并且R3是卤素。
8.根据前述权利要求中任一项所述的化合物，其中，R1是C1-C4卤代烷基。
9.根据前述权利要求中任一项所述的化合物，其中，R1是CF3。
10.根据前述权利要求中任一项所述的化合物，其中，R2选自由以下组成的组：卤素、C1-C4卤代烷基和C1-C4卤代烷氧基。
11.一种除草组合物，其包含根据前述权利要求中任一项所述的化合物和农业上可接受的配制辅助剂。
12.根据权利要求11所述的除草组合物，其进一步包含至少一种另外的杀有害生物剂。
13.根据权利要求12所述的除草组合物，其中，所述另外的杀有害生物剂是除草剂或除草剂安全剂。
14.一种在场所处控制杂草的方法，所述方法包括向所述场所施用控制杂草量的根据权利要求11至13中任一项所述的组合物。
15.根据权利要求1所述的具有式(I)的化合物作为除草剂的用途。
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