CN105492443A - 取代吡唑基吡唑衍生物及其作为除草剂的用途 - Google Patents
取代吡唑基吡唑衍生物及其作为除草剂的用途 Download PDFInfo
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- CN105492443A CN105492443A CN201480044198.1A CN201480044198A CN105492443A CN 105492443 A CN105492443 A CN 105492443A CN 201480044198 A CN201480044198 A CN 201480044198A CN 105492443 A CN105492443 A CN 105492443A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本发明提供一种能够有效防除在实用上成问题的更高叶龄的重要杂草的化合物。公开了能够解决上述课题的式(I)表示的特定的吡唑基吡唑衍生物。
Description
技术领域
本发明涉及取代吡唑基吡唑衍生物、以及该化合物作为除草剂的用途。
背景技术
近年来,在栽培农作物时使用大量的除草剂,有助于农业操作的省力化和提高农作物的生产性。在旱田、水稻栽培中许多除草剂已被实用化。
然而,杂草的种类多样化,而且各杂草的发芽和生长时期不一样,进而多年生杂草长期生长。因此,很难通过散布一次除草剂来防除所有的杂草。
水稻的初中期一次性处理剂显示出在直到稗草(ノビエ)(稻稗(Echinochloaoryzicola)、野稗(Echinochloacrus-gallivar.crus-galli)、台湾野稗(Echinochloacrus-gallivar.formosensis)、细叶旱稗(Echinochloacrus-gallivar.praticola)、长芒稗(Echinochloacrus-gallivar.caudata)的总称)的2~3叶期的处理中有效,经过一次处理可以防除主要杂草(参考非专利文献1)。但是,在实用化的初中期一次性处理剂中,防除稗草在生长至3.5叶期以上的时期的杂草是非常困难的,稗草的3叶期时的防除与3.5叶期时的防除存在着技术鸿沟。
进而,长期维持除草效果(残效性)在减少农药散布、操作的省力化、降低成本方面很重要,成为初中期一次性处理剂所必须的性能。
另外,近年来ALS(乙酰乳酸合成酶)抑制剂被广泛普及,对ALS抑制剂具有抵抗性的杂草成为问题。尤其对多年生的野慈姑(Sagittariatrifolia)、矮慈姑(Sagittariapygmaea)的ALS抑制剂抵抗性生物型具有充分效果的除草剂很少。另外,作为近年来成问题的杂草,多年生杂草中可列举出野荸荠(Eleochariskuroguwai)、扁秆藨草(Scirpusplaniculmis)、三江藨草(Scirpusnipponicus)等,一年生杂草中可列举出合萌(Aeschynomeneindica)、千金子(Leptochloachinensis)、疣草(Murdanniakeisak)等,对这些难防除杂草具有充分效果的除草剂很少。
另一方面,许多吡唑衍生物作为除草剂而被实用化,例如4-(2,4-二氯苯甲酰基)-1,3-二甲基-5-吡唑基对甲苯磺酸酯(通用名:“吡唑特(Pyrazolate)”)、2-[4-(2,4-二氯苯甲酰基)-1,3-二甲基吡唑-5-基氧基]乙酰苯(通用名:“苄草唑(Pyrazoxyfen)”)、2-[4-(2,4-二氯间甲苯酰基)-1,3-二甲基吡唑-5-基氧基]-4’-甲基乙酰苯(通用名:“吡草酮(Benzofenap)”)等被广泛使用,但是这些除草剂的单剂在日本注册的对稗草的适用范围均是直到1.5叶期,这些吡唑衍生物虽对广范围的杂草有效,但对高叶龄的稗草的效果未必充分。
另外,专利文献1记载的实施例4.73的化合物1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-5-[甲基(丙-2-炔基)氨基]吡唑-4-腈(通用名:“双唑草腈(Pyraclonil)”,商品名:ピラクロン)对广范围的杂草有效,但对高叶龄的稗草的效果不充分,在日本注册的这种除草剂单剂对稗草的适用范围是直到1.5叶期。
现有技术文献
专利文献
专利文献1:WO94/08999
非专利文献
非专利文献1:水田杂草の生态及其防除-水稻作物的杂草和除草剂解说-159页(水田雑草の生態とその防除―水稲作の雑草と除草剤解説―159頁)。
发明内容
发明要解决的问题
本发明的目的在于提供一种具有广泛杀草谱,能够防除实用上成问题的更高叶龄的重要杂草,并且对水稻等作物不产生药害的除草剂组合物。
用于解决问题的方案
本发明人等为达成上述目的进行了反复深入研究,结果发现具有特定化学结构的吡唑基吡唑衍生物长期具有广泛的杀草谱,而且对高叶龄的重要杂草显示出优异的除草效力,另一方面,对栽培作物具有充分的安全性,从而根据此见解完成了本发明。因此,本发明提供下式(I)代表的化合物,即吡唑基吡唑衍生物;
上式中:
R1表示卤素原子,
R2表示氰基、硝基,
R3表示被一个以上的卤素原子取代的C2~C4烷基、C1~C2烷氧基(C1~C3)烷基,
a表示3~5,且
b表示1~3。
具体实施方式
本说明书中:
各取代基之前的如“Ca~Cb”的记载是指,各自所对应的基团中碳原子存在a个~b个。
“卤素原子”包括氟、氯、溴和碘原子。
“烷基”可为直链状或支链状,并且取代基中所含氢原子的至少一个可被卤素原子取代,没有限制,例如可列举出氯乙基、二氯乙基、三氟乙基、四氟丙基、溴乙基、溴丙基、氯丁基等,可在指定的碳原子数范围内进行选择。
“烷氧基”是指烷基部分具有上述含义的烷基-O-基团,没有限制,例如可列举出甲氧基、乙氧基等,可在各自指定的碳原子数范围内进行选择。
在上述基团或其一部分被卤素原子多取代的情况下,该基团可被多于一个的相同或不同的卤素原子和/或取代基取代。
以下列举的所有化学式中,取代基和符号只要没有另行定义,均具有与对式(I)的定义相同的含义。本发明所提供的式(I)的化合物例如可通过式(II)代表的化合物的烷基化,然后全氟酰胺化反应而简便地合成;
式(II):
。
式(II)的化合物可按照WO93/10100和WO94/08999记载的方法,由四氢-2H-吡喃-2-亚基乙腈、或者5-氯戊酰氯合成。
式(II)的化合物的烷基化反应可以参考公知的反应条件而进行(例如参照WO94/08999)。根据情况,可以按照保护氨基、烷基化、脱保护的步骤进行。
接着,全氟酰胺化反应可以在公知的反应条件下,以及采用其中所引用的文献中记载的公知方法容易地制备(例如参照日本特开2005-154420)。
由后述试验例1~3中记载的除草活性试验的结果表明,本发明提供的式(I)的化合物具有优异的除草效果,作为除草剂有用。
本发明的式(I)的化合物对多种农耕地杂草和非农耕地杂草具有活性。作为栽培植物,可列举例如稻子、小麦、大麦、玉米、燕麦、高粱等禾木科植物;大豆、棉花、甜菜、向日葵、油菜子等阔叶作物,除此之外还可列举出果树、果菜类、根菜类、叶菜类等蔬菜、草等,可在这些植物的栽培中使用。
本发明的化合物对于水田中以下列举的成问题的各种杂草,在灌溉或非灌溉状态下的土壤处理、土壤混和处理、以及茎叶处理的任意处理方法中均具有除草效力。以下对该杂草进行示例,但并不限于此例。
作为可由本发明的式(I)的化合物防除的水田杂草,例如可列举出:窄叶泽泻(Alismacanaliculatum)、野慈姑(Sagittariatrifolia)、矮慈姑(Sagittariapygmaea)等泽泻科杂草;异型莎草(Cyperusdifformis)、水莎草(Cyperusserotinus)、萤蔺(Scirpusjuncoides)、野荸荠(Eleochariskuroguwai)、扁秆藨草(Scirpusplaniculmis)、三江藨草(Scirpusnipponicus)等莎草科杂草;陌上菜(Linderniaprocumbens)、北美母草(タケトアゼナ)(Linderniadubiasubsp.dubia)、美洲母草(Linderniadubia)等玄参科杂草;鸭舌草(Monochoriavaginalis)、雨久花(Monochoriakorsakowii)等雨久花科杂草;眼子菜(Potamogetondistinctus)等眼子菜科杂草;节节菜(Rotalaindica)、多花水苋(Ammanniamultiflora)等千屈菜科杂草;狼杷草(Bidenstripartita)、大狼把草(Bidensfrondosa)等菊科杂草;合萌(Aeschynomeneindica)等豆科杂草;疣草(Murdanniakeisak)等鸭跖草科杂草;稻稗(Echinochloaoryzicola)、野稗(Echinochloacrus-gallivar.crus-galli)、台湾野稗(Echinochloacrus-gallivar.formosensis)、细叶旱稗(Echinochloacrus-gallivar.praticola)、长芒稗(Echinochloacrus-gallivar.caudata)、千金子(Leptochloachinensis)、假稻(Leersiajaponica)、双穗雀稗(Paspalumdistichum)、蓉草(Leersiaoryzoides)等禾木科杂草等。
另外,对于旱田、非农耕地中以下列举的成问题的各种杂草,在土壤处理、土壤混和处理和茎叶处理的任意处理方法中均具有除草效力。以下对该杂草进行示例,但并不限于此例;
可列举出:龙葵(Solanumnigrum)、曼陀罗(Daturastramonium)等茄科杂草;苘麻(Abutilonavicennae)、刺金午时花(Sidaspinosa)等锦葵科杂草;圆叶牵牛(Ipomoeapurpurea)等旋花科杂草;凹头苋(Amaranthuslividus)等苋科杂草;苍耳(Xanthiumstrumarium)、豚草(Ambrosiaartemisiifolia)、睫毛牛膝菊(Galinsogaciliata)、丝路蓟(Cirsiumarvense)、欧洲千里光(Seneciovulgaris)、一年蓬(Stenactisannuus)等菊科杂草;蔊菜(Rorippaindica)、野芥(Sinapisarvensis)、荠菜(Capsellabursa-pastoris)等十字花科杂草;犬蓼(Persicarialongiseta)、卷茎蓼(Fallopiaconvolvulus)等蓼科杂草;马齿苋(Portulacaoleracea)等马齿苋科杂草;藜(Chenopodiumalbum)、小叶灰藋(Chenopodiumficifolium)、地肤(Kochiascoparia)等藜科杂草;繁缕(Stellariamedia)等石竹科杂草;阿拉伯婆婆纳(Veronicapersica)等玄参科杂草;鸭跖草(Commelinacommunis)等鸭跖草科杂草;宝盖草(Lamiumamplexicaule)、小野芝麻(Lamiumpurpureum)等唇形科杂草;斑地锦(コニシキソウ)(Euphorbiasupina)、斑地锦(オオニシキソウ)(Euphorbiamaculata)等大戟科杂草;猪秧秧(Galiumspurium)、刺籽爬拉殃(Galiumspuriumvar.echinospermon)、东南茜草(Rubiaargyi)等茜草科杂草;东北堇菜(Violamandshurica)等堇菜科杂草;田菁(Sesbaniaexaltata)、决明(Cassiaobfusitolia)等豆科杂草等阔叶杂草;高粱(Sorghumbicolor)、洋野黍(Panicumdichotomiflorum)、石茅(Sorghumhalepense)、野稗(Echinochloacrus-gallivar.crus-galli)、升马唐(Digitariaciliaris)、野燕麦(Avenafatua)、牛筋草(Eleusineindica)、狗尾草(Setariaviridis)、看麦娘(Alopecurusaequalis)、早熟禾(Poaannua)等禾木科杂草;香附子(Cyperusrotundus)等莎草科杂草等。
进而,可以对收割的刈痕(刈り取り跡)、休耕地、果园地、牧草地、草坪地、轨道沿线(線路端)、空地、林地、或者农业用道路、畦畔、其他非农耕地中产生的广范围的杂草进行除草。
而且,本发明的式(I)的化合物在水稻的直播栽培或移植栽培等任意栽培方法中均未出现对水稻产生问题那样的药害。
本发明的式(I)的化合物在植物发芽前和发芽后均可施用,进而,也可以在播种前混合于土壤中。
本发明的式(I)的化合物的投药量可以根据化合物的种类、对象植物的种类、使用时期、使用场所、可期效果的性质等在广范围内改变,作为大致的基准,以每公亩的活性化合物计,例如可示例在约0.01~100g、优选在约0.1~10g的范围内。
本发明的式(I)的化合物也可以单独使用,但通常可按照常规方法在式(I)的化合物中配合配方助剂(formulationassistant)等,没有限制,例如可以制剂成粉剂、乳剂、油剂(油剤)、增溶剂、悬乳剂(suspo-emulsion)、微粒剂、喷雾剂、DL粉剂、微粒剂F、细粒剂F、粒剂、可湿性粉剂(水和剤)、水分散粒剂(顆粒水和剤)、悬浮剂(flowableconcentrate)、Jumbo(ジャンボ)剂、片剂、糊剂、油性悬浮液、水溶性化学剂(水溶剤)、水溶性粒剂(顆粒水溶剤)、液剂、微胶囊剂等任意剂型来使用。
作为可用于制剂化的配方助剂,没有限制,例如可列举出固体载体、液体载体、粘合剂、增粘剂、表面活性剂、防冻剂、防腐剂等。
作为固体载体,没有限制,例如可列举出滑石、膨润土、蒙脱石、粘土、高岭土、碳酸钙、碳酸钠、碳酸氢钠、芒硝、沸石、淀粉、酸性粘土、硅藻土、白炭黑(ホワイトカーボン)、蛭石、消石灰、植物性粉末、氧化铝、活性炭、糖类、玻璃空心体、硅砂、硫酸铵、尿素等。
作为液体载体,没有限制,例如可列举出烃类(例如煤油、矿物油等);芳族烃类(例如甲苯、二甲苯、二甲基萘、苯基二甲苯基乙烷等);氯化烃类(例如氯仿、四氯化碳等);醚类(例如二噁烷、四氢呋喃等);酮类(例如丙酮、环己酮、异佛尔酮等);酯类(例如乙酸乙酯、乙酸乙二醇酯、马来酸二丁酯等);醇类(例如甲醇、正己醇、乙二醇等);极性溶剂类(例如N,N-二甲基甲酰胺、二甲基亚砜、N-甲基吡咯烷酮等);水等。
作为粘合剂和增粘剂,没有限制,例如可列举出糊精、羧甲基纤维素的钠盐、聚羧酸(polycarboxylicacid)系高分子化合物、聚乙烯吡咯烷酮、聚乙烯醇、木素磺酸钠、木素磺酸钙、聚丙烯酸钠、阿拉伯胶、海藻酸钠、甘露醇、山梨醇、膨润土系矿物质、聚丙烯酸及其衍生物、白炭黑、天然的糖类衍生物(例如黄原胶、瓜尔胶等)等。
作为表面活性剂,没有限制,例如可列举出:脂肪酸盐、苯甲酸盐、烷基磺基琥珀酸盐、二烷基磺基琥珀酸盐、聚羧酸盐、烷基硫酸酯盐、烷基硫酸盐、烷基芳基硫酸盐、烷基二甘醇醚硫酸盐、醇硫酸酯盐、烷基磺酸盐、烷基芳基磺酸盐、芳基磺酸盐、木素磺酸盐、烷基二苯基醚二磺酸盐、聚苯乙烯磺酸盐、烷基磷酸酯盐、烷基芳基磷酸盐、苯乙烯基芳基磷酸盐、聚氧乙烯烷基醚硫酸酯盐、聚氧乙烯烷基芳基醚硫酸盐、聚氧乙烯烷基芳基醚硫酸酯盐、聚氧乙烯烷基醚磷酸盐、聚氧乙烯烷基芳基磷酸酯盐、萘磺酸甲醛缩合物的盐等阴离子型表面活性剂;以及脱水山梨醇脂肪酸酯、甘油脂肪酸酯、脂肪酸聚甘油酯、脂肪酸醇聚乙二醇醚、炔属二醇(acetyleneglycol)、炔属醇、氧化烯嵌段聚合物、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯苯乙烯基芳基醚、聚氧乙烯二醇烷基醚、聚氧乙烯脂肪酸酯、聚氧乙烯脱水山梨醇脂肪酸酯、聚氧乙烯甘油脂肪酸酯、聚氧乙烯加氢蓖麻油、聚氧丙烯脂肪酸酯等非离子型表面活性剂。
作为防冻剂,没有限制,例如可列举出乙二醇、二甘醇和丙二醇、甘油等。
作为防腐剂,没有限制,例如可列举出苯甲酸、苯甲酸钠、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、异丙基甲酚、苯扎氯铵、盐酸氯己定、双氧水、葡萄糖酸氯己定、水杨酸、水杨酸钠、吡硫锌(zincpyrithione)、山梨酸、山梨酸钾、脱氢乙酸、脱氢乙酸钠、苯氧乙醇、5-氯-2-甲基-4-异噻唑啉-3-酮、2-甲基-4-异噻唑啉-3-酮等异噻唑啉衍生物、2-溴-2-硝基丙烷-1,3-二醇、以及水杨酸衍生物。
以上所述固体载体、液体载体、粘合剂、增粘剂、表面活性剂、防冻剂和防腐剂可以根据使用目的等各自单独使用或适当组合使用。
本发明的式(I)的化合物相对于本发明的除草剂组合物总量的配合比例可以根据需要增减,没有特别限制,通常为0.01~90质量%左右,在制成例如粉剂或粒剂的情况下优选为0.1~50质量%左右,更优选为0.5~10质量%左右,在制成乳剂、可湿性粉剂或水分散粒剂等的情况下优选为0.1~90质量%左右,更优选为0.5~50质量%左右。
这些制剂可以根据需要稀释为适当浓度,通过散布于植物茎叶、土壤、水田的水面等或者直接施用,供于各种用途。
通过以下实施例对本发明进行说明。
实施例
实施例1.N-(2-氯乙基)-N-(1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)-2,2,2-三氟乙酰胺的制法(化合物1)
向冷却至5℃的乙酸酐(33.7g)中缓慢滴加甲酸(18.4g),60℃下搅拌2小时(反应液A)。另行将5-氨基-1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)吡唑-4-腈(26.3g)溶解于乙腈(200ml)中,进行搅拌。向其中缓慢滴加先前制备的反应液A,室温下反应1天、60℃下反应4小时。然后,减压蒸馏除去溶剂,用碳酸钾水溶液中和,析出的固体用水洗涤,干燥后得到N-(1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)甲酰胺(28g)。
将所得的N-(1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)甲酰胺(4.4g)溶解于N,N-二甲基甲酰胺(15ml)中,加入碳酸钾(2.5g),进行搅拌。向其中缓慢滴加1-溴-2-氯乙烷(2.6g),50℃下反应6小时,反应结束后,向反应液中加入水,用乙酸乙酯萃取。用硫酸钠干燥后,将溶剂减压浓缩,得到粗产物(5.2g)。
将所得粗产物(5.2g)溶解于乙醇(20ml)中,加入10%盐酸(5.5g),65℃下搅拌3小时。反应结束后,向反应液中加入水,将析出的固体滤出,干燥后,得到1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-5-(2-氯乙基氨基)吡唑-4-腈(4.5g)。
将1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-5-(2-氯乙基氨基)吡唑-4-腈(1.0g)溶解于乙腈(6ml)中,搅拌后,向其中缓慢滴加三氟乙酸酐(3.2g)。40℃下搅拌4天,向反应液中加入饱和碳酸氢钠水溶液,用乙酸乙酯萃取。用硫酸钠干燥后,减压蒸馏除去溶剂,所得粗产物用硅胶柱色谱(己烷/乙酸乙酯=1:1)纯化,得到目标产物(0.9g)。
实施例2.N-(1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)-N-(2-甲氧基乙基)-2,2,2-三氟乙酰胺的制法(化合物2)
将5-氨基-1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)吡唑-4-腈(43.1g)溶解于N,N-二甲基甲酰胺(170ml)中,加入55%氢化钠(8.6g),进行搅拌。确认发泡平息后,边用冰浴冷却反应液边缓慢滴加2-溴乙基甲基醚(25g),滴加结束后在60℃下反应8小时。反应结束后,向反应液中加入水,将析出的固体用乙酸乙酯洗涤,得到1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-5-(2-甲氧基乙基氨基)吡唑-4-腈(36g)。向所得的1-(3-氯-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基)-5-(2-甲氧基乙基氨基)吡唑-4-腈(20g)中加入乙腈(65ml),向其中缓慢滴加三氟乙酸酐(14.4g)。50℃下搅拌10小时,向反应液中加入饱和碳酸氢钠水溶液,用乙酸乙酯萃取。用硫酸钠干燥后,将溶剂减压浓缩,利用重结晶(乙酸乙酯/己烷)将所得粗产物纯化,得到目标产物(22.7g)。
起始原料即式(II)的化合物按照WO93/10100和WO94/08999合成。
下表中所列实施例采用与上述方法同样的方式制成,或者采用与上述方法同样的方式得到。
[表1]
。
[表2]
。
<制剂实施例>
1.粉剂
式(I)的化合物10重量份
滑石90重量份
将上述成分混合,用锤磨机微粉碎而得到。
2.可湿性粉剂
式(I)的化合物10重量份
聚氧乙烯烷基芳基醚硫酸盐22.5重量份
白炭黑67.5重量份
将上述成分混合,将该混合物用锤磨机微粉碎而得到。
3.悬浮剂
式(I)的化合物10重量份
聚氧乙烯烷基醚磷酸盐10重量份
膨润土5重量份
乙二醇5重量份
水70重量份
将上述成分混合,使用湿式粉碎机进行粉碎而得到悬浮剂。
4.乳剂
式(I)的化合物15重量份
乙氧基化壬基苯酚10重量份
环己酮75重量份
将上述成分混合,得到乳剂。
5.粒剂
式(I)的化合物5重量份
木素磺酸钙3重量份
聚羧酸盐3重量份
碳酸钙89重量份
将上述成分混合,加入水捏合后挤出造粒。然后干燥、整粒,得到粒剂。
<生物试验实施例>
1.水田除草试验
在1/10000公亩的盆中填充水田土壤,加入适量水和化学肥料进行捏合,播种稗草、鸭舌草和萤蔺的种子,保持水深3cm的灌溉状态。
用适量水稀释按照制剂例制备的表1所示目标化合物(I)的可湿性粉剂,在3.5叶期的稗草中移植2.0叶期的稻子,用移液管进行滴加处理,使每公亩达到规定药量。
于是,在平均气温30℃的玻璃屋内管理30天后,对它们的除草效果进行研究。
除草效果的评价是与未处理区的状态比较生长抑制率(%),药害的评价是与完全除草区的状态比较生长抑制率(%),表示为以下11个等级;
0(指数):0%~小于10%(生长抑制率)、
1:10%以上~小于20%、
2:20%以上~小于30%、
3:30%以上~小于40%、
4:40%以上~小于50%、
5:50%以上~小于60%、
6:60%以上~小于70%、
7:70%以上~小于80%、
8:80%以上~小于90%、
9:90%以上~小于100%、
10:100%
其结果示于表2。
对照剂4.63(WO94/08999记载)
对照剂4.92(WO94/08999记载)
对照剂4.185(WO94/08999记载)
对照剂4.237(WO94/08999记载)
对照剂4.238(WO94/08999记载)
。
[表3]
。
2.旱田作物土壤处理试验
在1/6000公亩的盆中填充旱田土壤,播种升马唐、藜、皱果苋(アオビユ)的种子并盖土。
用水将按照制剂例制备的表1所示式(I)的化合物的可湿性粉剂稀释至规定药量,在播种之后长出杂草之前,以每公亩10升的散布水量对各土壤表层均匀进行喷雾处理。
然后在平均气温30℃的玻璃屋内管理30天后,对它们的除草效果进行研究。
除草效果的评价采用与上述试验例1同样的方式进行。
其结果示于表3。
[表4]
。
3.旱田作物茎叶处理试验
在1/6000公亩的盆中填充培土,播种升马唐、藜、皱果苋的种子并盖土,在平均气温25℃的玻璃屋内进行栽培。
在升马唐生长至1.0~2.0叶期的时期,用水将按照制剂例制备的表1所示目标化合物(I)的可湿性粉剂稀释至规定药量,以每公亩15升的散布水量在杂草上均匀进行喷雾处理。
然后在平均气温25℃的玻璃屋内管理3周后,对它们的除草效果进行研究。
除草效果的评价采用与上述试验例1同样的方式进行。
其结果示于表4。
[表5]
。
产业适用性
根据本发明,本发明的式(I)的化合物对不需要的植物具有优异的防除效果,因此作为有害植物防除剂有用。
Claims (6)
1.下式(I)表示的化合物:
式中,
R1表示卤素原子,
R2表示氰基、硝基,
R3表示被一个以上的卤素原子取代的C2~C4烷基、C1~C2烷氧基-C1~C3-烷基,
a表示3~5,而且
b表示1~3。
2.除草剂组合物,其包含除草有效量的权利要求1所述的化合物的至少一种。
3.权利要求2所述的除草剂组合物,其进一步包含配方助剂。
4.不需要的植物的防除方法,其包括:将有效量的权利要求1所述的化合物的至少一种、或者权利要求2或3所述的除草剂组合物施用于不需要的植物或不需要的植被的场所。
5.权利要求1所述的化合物或者权利要求2或3所述的除草剂组合物在用于防除不需要的植物中的用途。
6.权利要求5所述的用途,其中,权利要求1所述的化合物用于防除有用植物的农作物中的不需要的植物。
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CN112341456A (zh) * | 2019-08-07 | 2021-02-09 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑双酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
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TW201632521A (zh) | 2015-01-23 | 2016-09-16 | 協友股份有限公司 | 經取代之吡唑吡唑衍生物及其作爲除草劑的用途 |
TW201630908A (zh) * | 2015-01-23 | 2016-09-01 | 協友股份有限公司 | 經取代之吡唑吡唑衍生物及其作爲除草劑的用途 |
TW201632515A (zh) * | 2015-01-23 | 2016-09-16 | 協友股份有限公司 | 經取代之吡唑吡唑衍生物及其作爲除草劑的用途 |
JP2016141628A (ja) * | 2015-01-30 | 2016-08-08 | 協友アグリ株式会社 | 除草剤組成物 |
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CN110551122A (zh) * | 2018-06-04 | 2019-12-10 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
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CN110551122B (zh) * | 2018-06-04 | 2022-02-18 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
CN112341456A (zh) * | 2019-08-07 | 2021-02-09 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑双酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
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RU2016108489A (ru) | 2017-09-19 |
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RU2016108489A3 (zh) | 2018-05-29 |
UA115820C2 (uk) | 2017-12-26 |
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