CN107108622B - 经取代的吡唑基吡唑衍生物及其作为除草剂的用途 - Google Patents
经取代的吡唑基吡唑衍生物及其作为除草剂的用途 Download PDFInfo
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- CN107108622B CN107108622B CN201680006853.3A CN201680006853A CN107108622B CN 107108622 B CN107108622 B CN 107108622B CN 201680006853 A CN201680006853 A CN 201680006853A CN 107108622 B CN107108622 B CN 107108622B
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Classifications
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Abstract
本发明的课题在于提供可有效地防治实用上成为问题的较高叶龄的重要杂草的化合物。本发明的解决手段是公开可以解决上述课题的式(I)所表示的特定吡唑基吡唑衍生物。
Description
技术领域
本发明涉及经取代的吡唑基吡唑衍生物、及该化合物作为除草剂的利用。
背景技术
近年来,对于农作物的栽培,使用许多的除草剂而有助于农业劳作的省力化或农作物的生产性提高。在旱田、水稻栽培中已有许多除草剂被实用化。
然而,杂草的种类繁多,且各种杂草的发芽和生长时期不同,并且,多年生杂草的发生为长期的。因此以一次除草剂喷洒来防治所有杂草是非常困难的。
水稻的早中期单次处理剂在野稗(田犬稗(Echinochloa oryzicola)、犬稗(Echinochloa crus-galli var.crus-galli)、姫田犬稗(Echinochloa crus-galli var.formosensis)、姫犬稗(Echinochloa crus-galli var. praticola)、毛犬稗(Echinochloacrus-galli var. caudata)的总称)的2~3叶期为止的处理显示为有效的,可以一次处理而防治主要杂草(参考非专利文献1)。但是,对于已实用化的早中期单次处理剂,防治野稗已生长至3.5叶期以上的时期的杂草是非常困难的,对野稗的3叶期时的防治和3.5叶期时的防治,在技术上有很大的隔绝。
并且,长期间的除草效果的维持(或残效性)在农药喷洒的减低、操作的省力化、成本削减等方面是重要的,在早中期单次处理剂中被视为是所必要的性能。
另外,近年来ALS(乙酰乳酸合成酶)抑制剂广泛普及,对ALS抑制剂具有抵抗性的杂草成为问题。尤其,对多年生的野慈菇(Sagittaria trifolia)或矮慈菇(Sagittariapygmaea )的抗ALS抑制剂性生物型具有充分效果的除草剂少。另外,作为近年来成为问题的杂草,多年生中可举出:野荸荠(Eleocharis kuroguwai)、扁秆藨草(Scirpusplaniculmis)、三江藨草(Scirpus nipponicus)等;一年生中可举出:合萌(Aeschynomeneindica)、千金子(Leptochloa chinensis)、疣草(Murdannia keisak)等,对这些难防治杂草具有充分效果的除草剂少。
另一方面,许多吡唑衍生物作为除草剂而被实用化,例如可以广泛使用: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]苯乙酮(通用名:“普芬草(Pyrazoxyfen)”)、2-[4-(2,4-二氯-间甲苯酰基)-1,3-二甲基吡唑-5-基氧基]-4’-甲基苯乙酮(通用名:“吡草酮(Benzofenap)”)等,但任一单剂均在日本为注册上对野稗的适用范围是至1.5叶期为止,这些吡唑衍生物对广范围的杂草有效,但对高叶龄的野稗的效果未必充分。
另外,专利文献1中记载的实施例4.73的化合物即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-甲腈(通用名:“双唑草腈(Pyraclonil)”,商品名Pyraclon)对广范围的杂草有效,但对高叶龄的野稗的效果并不充分,在日本的注册上的本剂单剂的对野稗的适用范围是至1.5叶期为止。
并且,专利文献1中虽然也公开关于对于旱田长出的杂草通过长出前和长出后处理而显示除草效果的化合物,但关于叶龄并无记载,不能说这些化合物对高叶龄的杂草具有充分的效果。另外,作为对旱田的杂草显示广范围的除草效果的除草剂,例如已广泛使用异丙基铵N-(膦酰甲基)甘氨酸酯(通用名:“草甘膦异丙基胺盐”),但近年来产生抵抗性的杂草发生等的课题。
此外,近年来,产生了农药所致的地下水和河流水的污染问题。因此,正谋求有效成分对施用处所以外流出的可能性低等,对环境的影响被控制到最小限度的除草剂的开发。
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:水田雑草の生態とその防除―水稲作の雑草と除草剤解説(水田杂草的生态及其防治-水稻作的杂草与除草剂解说)-159页。
发明内容
发明所要解决的课题
本发明的目的在于提供一种化合物,其是作为除草剂成分而具有下述的优异特性:具有包含对现有的除草剂具有抵抗性的杂草的广泛杀草谱,可防治实用上成为问题的较高叶龄的重要杂草,且对水稻等的作物不产生药害等。
用于解决课题的手段
本发明人为了实现前述目的,不断专心研究的结果,发现了具有特定化学结构的吡唑基吡唑衍生物尤其在长期间中具有广范围的杀草谱的同时,对高叶龄的重要杂草显示优异的除草效力,另一方面,对栽培作物具有充分的安全性,并基于如此见解,完成了本发明。
因此,本发明提供下述式(I)所示的化合物的吡唑基吡唑衍生物。
[化学式1]
上式中,
R1表示氯原子、溴原子,
R2表示氰基、硝基,
R3视情况可被卤素原子、羟基、氰基、硝基、或者(视情况被1个或更多的卤素原子所取代的)C1~C4烷基、或者(视情况被1个或更多的卤素原子所取代的)C1~C4烷氧基所取代,
a表示3~5,
b表示1~3,且
c表示1~5,而c表示2以上时,各自的R3可彼此相同或彼此不同。
式(I)中,优选:
R1表示氯原子,
R2表示氰基,
a表示4,
b表示1,且
c表示1。
本说明书中,如各取代基之前的“Ca~Cb”的记载,分别是指该基团中存在a个~b个碳原子。
“卤素原子”包含氟、氯、溴和碘原子。
基团的本身或基团的部分所言及的“烷基”可为直链状或支链状,不受限定,例如可举出:甲基、乙基、正或异丙基、正、异、仲或叔丁基等,在各自指定的碳原子数的范围内选择。
对于“烷基”,这些基团所含的氢原子的至少1个可被卤素原子所取代,例如若以烷基为例,则不受限定,可为氯甲基、二氯甲基、三氟甲基、氯乙基、二氯乙基、三氟乙基、四氟丙基、溴乙基、溴丙基、氯丁基,在各自指定的碳原子数的范围内选择。
“烷氧基”是指烷基部分具有上述含义的烷基-O-基,不受限定,例如可举出:甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基等,在各自指定的碳原子数的范围内选择。
前述的基团或者部分被卤素原子多取代的情形,该基团可被多于1个的相同或不同的卤素原子所取代。
以下列举的所有的式中,取代基和记号除非另外定义,否则具有与式(I)中定义者相同的含义。本发明所提供的式(I)的化合物中R3为氢原子者,可由式(II)所示的化合物的酰胺化反应而简便地合成。[化学式2]
式(II)的化合物可按照WO93/10100和WO94/08999 中记载的方法,由四氢-2H-吡喃-2-亚基乙腈或者5-氯戊酰氯合成。
式(II)的化合物的酰胺化反应本身可参考公知的反应条件来实施(例如,参照WO94/08999、Tetrahedron Lett. 32,4019(1991))。
本发明所提供的式(I)的化合物,如由后述的试验例1~4中记载的除草活性试验的结果可知,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,除了例如可举出稻、小麦、大麦、玉米、燕麦、高粱等的禾木科植物;或大豆、棉、甜菜、向日葵、油菜子等的阔叶作物之外,还有果树、果菜类或根菜类、叶菜类等的蔬菜、草坪地等,可用于它们的栽培。
本发明的化合物在水田中对下列所举出的成为问题的各种杂草,在以注水或者未注水的状态的土壤处理、土壤混合处理和茎叶处理的任一处理方法中均具有除草效力。以下例示该杂草,但不限于这些实例。
作为可通过本发明的式(I)的化合物而防治的水田杂草,例如可举出:窄叶泽泻(Alisma canaliculatum)、野慈菇(Sagittaria trifolia)、矮慈菇(Sagittaria pygmaea)等的泽泻科杂草;异型莎草(Cyperus difformis)、水莎草(Cyperus serotinus)、萤蔺(Scirpus juncoides)、野荸荠(Eleocharis kuroguwai)、扁秆藨草(Scirpusplaniculmis)、三江藨草(Scirpus nipponicus)等的莎草科杂草;陌上菜(Linderniaprocumbens)、北美母草杜比亚亚种(Lindernia dubia subsp. dubia)、美洲母草(Lindernia dubia)等的玄参科杂草;鸭舌草(Monochoria vaginalis)、雨久花(Monochoriakorsakowii)等的雨久花科杂草;眼子菜(Potamogeton distinctus)等的眼子菜科杂草;节节菜(Rotala indica)、多花水苋菜(Ammannia multiflora)等的千屈菜科杂草;狼把草(Bidens tripartita)、大狼耙草(Bidens frondosa)等的菊科杂草;合萌(Aeschynomene indica)等的豆科杂草;疣草(Murdannia keisak)等的鸭跖草科杂草;田犬稗(Echinochloa oryzicola)、犬稗(Echinochloa crus-galli var.crus-galli)、姫田犬稗(Echinochloa crus-galli var. formosensis)、姫犬稗(Echinochloa crus-gallivar. praticola)、毛犬稗(Echinochloa crus-galli var. caudata)、千金子(Leptochloachinensis)、假稻(Leersia japonica)、双穗雀稗(Paspalum distichum)、蓉草(Leersiaoryzoides)等的禾木科杂草等。
另外,作为旱田、非农耕地,对下列所举出的成为问题的各种杂草,在土壤处理、土壤混合处理和茎叶处理的任一处理方法中均具有除草效力。以下例示该杂草,但不限于这些实例。
可举出:龙葵(Solanum nigrum)、曼陀罗(Datura stramonium)等的茄科杂草;苘麻(Abutilon avicennae)、刺金午时花(Sida spinosa)、田旋花(Convolvulus arvensis)等的锦葵科杂草;紫花牵牛(Ipomoea purpurea)等的旋花科杂草;凹头苋(Amaranthuslividus)、反枝苋(Amaranthus retroflexus)、长芒苋(Amaranthus palmeri)、糙果苋(Amaranthus tuberculatus)等的苋科杂草;苍耳(Xanthium strumarium)、豚草(Ambrosiaartemisiifolia)、睫毛牛膝菊(Galinsoga ciliata)、丝路蓟(Cirsium arvense)、欧洲千里光(Senecio vulgaris)、一年蓬(Stenactis annuus)、牛膝菊(Galinsoga parviflora)、苦荬菜(Sonchus arvensis)、苦苣菜(Sonchus oleraceus)、甘菊(Matricaria inodora)等的菊科杂草;印度蔊菜(Rorippa indica)、野芥(Sinapis arvensis)、荠菜(Capsellabursa-pastoris)、菥蓂(Thlaspi arvense)等的十字花科杂草;犬蓼(Persicarialongiseta)、卷茎蓼(Fallopia convolvulus)、扁蓄(Polygonum aviculare var.condensatum)、扁蓄(Polygonum aviculare var. monospeliense)、春蓼(Polygonumpersicaria)、早苗蓼(Persicaria lapathifolia var. incana)、大犬蓼(Persicarialapathifolia var. lapathifolia)等的蓼科杂草;马齿苋(Portulaca oleracea)等的马齿苋科杂草;藜(Chenopodium album)、小藜(Chenopodium ficifolium)、地肤(Kochiascoparia)、草地滨藜(Atriplex patula)等的藜科杂草;繁缕(Stellaria media)等的石竹科杂草;***婆婆纳(Veronica persica)等的玄参科杂草;鸭跖草(Commelinacommunis)等的鸭跖草科杂草;宝盖草(Lamium amplexicaule)、紫花野芝麻(Lamiumpurpureum)、辣子草(Galeopsis tetrahit)等的唇形科杂草;小锦草(Euphorbia supina)、大锦草(Euphorbia maculata)等的大戟科杂草;猪殃殃(Galium spurium)、八重葎(Galiumspurium var. echinospermon)、东南茜草(Rubia argyi)、原拉拉藤(Galium aparine)等的茜草科杂草;紫花地丁(Viola mandshurica)、野生堇菜(Viola arvensis)等的堇菜科杂草;野地勿忘草(Myosotis arvensis)等的紫草科杂草;田菁(Sesbania exaltata)、决明(Cassia obfusitolia)等的豆科杂草等的阔叶杂草;高粱(Sorghum bicolor)、洋野黍(Panicum dichotomiflorum)、假高梁(Sorghum halepense)、犬稗(Echinochloa crus-galli var.crus-galli)、升马唐(Digitaria ciliaris)、野燕麦(Avena fatua)、牛筋草(Eleusine indica)、狗尾草(Setaria viridis)、看麦娘(Alopecurus aequalis)、早熟禾(Poa annua)、匍匐冰草(Agropyron repens)、狗牙根(Cynodon dactylon)、马唐(Digitaria sanguinalis)、金色狗尾草(Setaria pumila)、大穗看麦娘(Alopecurusmyosuroides)等的禾木科杂草;香附子(Cyperus rotundus)等的莎草科杂草等。
并且,可对收割后的迹地、休耕田、树园地、牧草地、草坪地、轨道边、空地、林业地、或者农道、田埂、其它的非农耕地发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的任意的栽培方法中都未显示对水稻成为问题的药害。
本发明的式(I)的化合物可于植物的发芽前和发芽后的任一者中施用,并且,也可在播种前混合于土壤中。
本发明的式(I)的化合物的给予量可根据化合物的种类、对象植物的种类、适用时期、适用场所、所希望效果的性质等而广范围变化,但就大致的标准而言,作为每1公亩的活性化合物,可例示约0.01~100g、优选约0.1~10g的范围内。
本发明的式(I)的化合物也可单独使用,但通常按照常规方法,向式(I)的化合物中掺混配方助剂等,不受限定,例如优选配制成下述的任意剂型而使用:散剂、乳剂、油剂、助溶剂、悬乳剂、微粒剂、喷雾剂、DL散剂、微粒剂F、细粒剂F、粒剂、水合剂、颗粒水合剂、可流动剂、大粒(Jumbo)剂、片剂、糊剂、油性悬浮液、水溶剂、颗粒水溶剂、液剂、微胶囊剂等。
作为可用于配制的配方助剂,不受限定,例如可举出: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,不受限定,例如可举出:滑石、膨润土、蒙脱石、陶土、高岭土、碳酸钙、碳酸钠、碳酸氢钠、芒硝、沸石、淀粉、酸性白土、硅藻土、白炭黑、蛭石、消石灰、植物性粉末、氧化铝、活性炭、糖类、玻璃中空体、硅砂、硫酸铵、尿素等。
作为液体载体,不受限定,例如可举出:烃类(例如,煤油、矿物油等);芳香族烃类(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、乙二醇乙酸酯、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、二甲亚砜、N-甲基吡咯烷酮等);水等。
作为粘合剂和增粘剂,不受限定,例如可举出:糊精、羧甲基纤维素的钠盐、聚羧酸类高分子化合物、聚乙烯吡咯烷酮、聚乙烯醇、木质素磺酸钠、木质素磺酸钙、聚丙烯酸钠、***树胶、褐藻酸钠、甘露糖醇、山梨糖醇、膨润土类矿物质、聚丙烯酸及其衍生物、白炭黑、天然糖类衍生物(例如,黄原胶、瓜尔胶等)等。
作为表面活性剂,不受限定,例如可举出: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、木质素磺酸盐、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***缩合物的盐等的阴离子系的表面活性剂和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、乙炔二醇、乙炔醇、氧化亚烷基嵌段聚合物、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、聚氧化乙烯二醇烷基醚、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、聚氧乙烯氢化蓖麻油、聚氧化丙烯脂肪酸酯等的非离子系的表面活性剂。
作为防冻剂,不受限定,例如可举出:乙二醇、二乙二醇和丙二醇、甘油等。
作为防腐剂,不受限定,例如可举出:苯甲酸、苯甲酸钠、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、异丙基甲基苯酚、苯扎氯铵、盐酸氯己啶、过氧化氢水溶液、葡糖酸氯己啶、水杨酸、水杨酸钠、吡啶硫酮锌、山梨酸、山梨酸钾、脱氢乙酸、脱氢乙酸钠、苯氧基乙醇、5-氯-2-甲基-4-异噻唑啉-3-酮、2-甲基-4-异噻唑啉-3-酮等的异噻唑啉衍生物、2-溴-2-硝基丙烷-1,3-二醇、和水杨酸衍生物。
可根据使用目的等,而将以上所述的固体载体、液体载体、粘合剂、增粘剂、表面活性剂、防冻剂和防腐剂各自单独或适当组合来使用
本发明的式(I)的化合物相对于本发明的除草剂组合物整体的掺混比例,可根据需要进行加减而不受特别限制,通常为0.01~90质量%左右,例如,制成散剂或粒剂时优选为0.1~50质量%左右,更优选为0.5~10质量%左右;制成乳剂、水合剂或颗粒水合剂等时优选为0.1~90质量%左右,更优选为0.5~50质量%左右。
这些制剂可根据需要稀释成适当的浓度来喷洒或直接施用于植物茎叶、土壤、水田的水面等,而供给于各种的用途。
通过以下的实施例说明本发明。
实施例
实施例1. 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-氟苯基)乙酰胺的制备方法(化合物1) 向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-甲腈(1.3g)中加入乙腈(5ml),向其中缓慢滴加2-氟苯基乙酰氯(1.0g),进行了8小时的加热回流。反应结束后,向反应液中加入水,用乙酸乙酯进行了萃取。用饱和碳酸氢钠水溶液洗涤后,用硫酸钠干燥,减压馏去了溶剂。将所得粗产物用异丙基醚洗浄,获得了目标物(1.9g)。
作为起始原料的式(II)按照WO93/10100和WO94/08999进行了合成。
下表所列举的实施例与上述方法同样地进行而制备、或与上述方法同样地进行而获得。
。
制剂实施例
1. 散剂
通过将
式(I)的化合物 10重量份
滑石 90重量份
混合并利用锤磨机进行微粉碎而获得。
2. 水合剂
通过将
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
混合并该混合物利用锤磨机进行微粉碎而获得。
3. 可流动剂
通过将
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
混合并使用湿式粉碎机进行粉碎而获得可流动剂。
4. 乳剂
通过将
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
混合而获得乳剂。
5. 粒剂
将
式(I)的化合物 5重量份
木质素磺酸钙 3重量份
聚羧酸盐 3重量份
碳酸钙 89重量份
混合并加入水,混炼后进行挤压而造粒。其后通过干燥、整粒而获得粒剂。
<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,加入适量的水和化学肥料进行混炼,将野稗、鸭舌草和萤蔺的种子进行播种,维持水深3cm的注水状态。
将依据制剂例所调制的表1所示目标化合物(I)的水合剂用适量的水进行稀释,并在野稗3.5叶期移植2.0叶期的稻,使用移液管以成为每10公亩规定的药量的方式进行了滴加处理。
然后,在平均气温30℃的玻璃温室中管理30天之后,研究了它们的除草效果。
除草效果的评价是与无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(%),而以下列11阶段表示。
0(指数):0%~不足10%(生长抑制率)、
1:10%以上~不足20%、
2:20%以上~不足30%、
3:30%以上~不足40%、
4:40%以上~不足50%、
5:50%以上~不足60%、
6:60%以上~不足70%、
7:70%以上~不足80%、
8:80%以上~不足90%、
9:90%以上~不足100%、
10:100%。
将其结果示于表2中。
对照剂2.19(WO94/08999记载)
[化学式3]
对照剂4.192(WO94/08999记载)
[化学式4]
2. 旱田耕作土壤处理试验
在1/6000公亩的盆中填充旱田土壤,将升马唐、藜、反枝苋的种子进行播种并覆土。
将依据制剂例所调制的表1所示式(I)的化合物的水合剂用水稀释成规定的药量,在播种后杂草发生前以每10公亩100L的喷洒水量,对各土壤表层均匀地进行喷雾处理。
然后,在平均气温30℃的玻璃温室中管理30天之后,研究了它们的除草效果。
除草效果的评价与前述试验例1同样地进行。
将其结果示于表3中。
3. 旱田耕作茎叶处理试验
在1/6000公亩的盆中填充培养土,将升马唐、藜、反枝苋的种子进行播种并覆土,在平均气温25℃的玻璃温室中进行栽培。
在升马唐生长成为1.0~2.0叶期的时期,将依据制剂例所调制的表1所示目标化合物(I)的水合剂用水稀释成规定的药量,以每10公亩150L的喷洒水量在杂草上均匀地进行喷雾处理。
然后,在平均气温25℃的玻璃温室中管理3周之后,研究了它们的除草效果。
除草效果的评价与前述试验例1同样地进行。
将其结果示于表4中。
4. 旱田耕作茎叶处理试验
在1/4500公亩盆中填充旱田土壤,将升马唐、牛膝菊(Galinsoga parviflora)的种子进行播种并覆土,在平均气温25℃的玻璃温室中进行栽培。
在升马唐生长成为4~5叶期(杂草高度10~15cm)的时期,将依据制剂例所调制的表1所示目标化合物(I)的水合剂用水稀释成规定量的药量,以每10公亩100L的喷洒水量在杂草上均匀地进行喷雾处理。
然后,在平均气温25℃的玻璃温室中管理20天之后,研究了它们的除草效果。
除草效果的评价与前述试验例1同样地进行。
将其结果示于表5中。
产业实用性
根据本发明,本发明的式(I)的化合物由于对于不需要的植物具有优异的防治效果,因此作为有害植物防治剂有用。
Claims (7)
1.下式(I)所示的化合物:
式中,
R1表示氯原子、溴原子,
R2表示氰基、硝基,
R3表示氢原子、卤素原子、羟基、氰基、硝基、视情况被1个或更多的卤素原子所取代的C1~C4烷基、或者视情况被1个或更多的卤素原子所取代的C1~C4烷氧基,
a表示3~5,
b表示1~3,且
c表示1~5,而c表示2以上时,各自的R3可彼此相同或彼此不同。
2.权利要求1所述的化合物,其中,R1表示氯原子,
R2表示氰基,
a表示4,
b表示1,且
c表示1。
3.除草剂组合物,其包含除草有效量的权利要求1或2所述的化合物的至少一种。
4.权利要求3所述的除草剂组合物,其中,进一步包含配方助剂。
5.防治不需要的植物的方法,其包含将有效量的权利要求1或2所述的化合物的至少一种或权利要求3或4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。
6.权利要求1或2所述的化合物或权利要求3或4所述的除草剂组合物的用途,其用于防治不需要的植物。
7.权利要求6所述的用途,其中,权利要求1或2所述的化合物用于防治有用植物的农作物中的不需要的植物。
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