CN115974857A - 一种新型硫代酰胺类化合物的制备方法及其应用 - Google Patents
一种新型硫代酰胺类化合物的制备方法及其应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及农用除草剂技术领域,具体而言,涉及一种新型硫代酰胺类化合物的制备方法及其应用。
背景技术
杂草的防治是实现高效农业过程中一个至关重要的环节,尽管市场上的除草剂种类多样,例如,WO2022238178A1、WO2022238247A1、WO2020079078A1等发明实施例了某些芳基甲酰胺类化合物及其作为除草剂的用途。由于多年长期使用,杂草抗性问题日益突出,尤其是随着五氟磺草胺、双草醚、氰氟草酯、恶唑酰草胺等以及草甘膦等市场主流杂草除草剂抗性的严重发生,小麦、水稻等作物遇到严峻挑战,缺乏有效防除抗性杂草的药剂,这就需要科学家们不断研究进而开发出新的高效、安全、经济以及具有不同作用方式的除草剂品种。
基于此,本发明提供了一种新型硫代酰胺类化合物及组合物、它们的用途及使用方法,所述化合物及其组合物的除草活性优异,且具有更高的作物安全性,尤其是对于水稻等关键农作物建立了良好的选择性。
鉴于此,特提出本发明。
发明内容
为了满足农业上的要求,本发明提供了一种新型硫代酰胺类化合物及其防除杂草的使用方法和含有这些化合物的组分在农业上的应用。
本发明是这样实现的:
本发明提供一种新型硫代酰胺类化合物或其可农用盐,如通式(Ⅰ)所示:
式中:
R1选自卤代C1-C3烷基;
R2、R3分别选自O、S;且R2、R3不同时选自O,至少有一个选自S;R4选自甲基或乙基;
可选的,所述通式(I)中:
R1选自卤代三氟甲烷基、二氟甲烷基;
R2、R3分别选自O,S;且R2、R3不同时选自O,至少有一个选自S;R4选自甲基或乙基;
可选的,所述通式(I)中,优选自如下结构:
可选的,通式(I)所示的化合物的盐选自通式(I)所示的化合物的钠盐、钾盐、钙盐和锂盐中的一种,优选为钠盐、钾盐和锂盐中的一种。
在上面给出的通式(I)化合物的定义中,汇集所用术语一般定义如下:
未取代表示所有取代基都为氢。
卤素:指氟、氯、溴或碘。
卤代烷基:直链或支链卤代烷基,在这些烷基上的氢原子可部分或全部被卤原子所取代,例如,卤代烷基诸如氯甲基、二氯甲基、三氯甲基、一氟甲基、二氟甲基或三氟甲基。
由以下通式(Ⅱ)表示的新型硫代酰胺类化合物与酸或碱加成的盐:
其中,R1、R2、R3、R4与通式(I)所定义的意义相同。
可以与本发明的由通式(Ⅱ)表示的新型硫代酰胺类化合物成盐的酸包括,羧酸,如乙酸、丙酸、丁酸、草酸、三氟乙酸;磺酸,如甲磺酸、对甲苯磺酸或十二烷基苯磺酸;及无机酸,如盐酸、硫酸、硝酸或碳酸。
可以与本发明的由通式(Ⅱ)表示的新型硫代酰胺类化合物成盐的碱及金属包括,金属,如钠、碱、钙、镁、等;有机碱,如甲醇钠、乙醇钠、叔丁醇钠、甲醇钾、乙醇钾、甲酸钠、丁基锂、乙酸钠等;无机碱,如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、氢氧化锂、碳酸锂、氢化钠、氨基钠等;
文中所使用的中间体除非另有说明,均为由市场购买得到。
本发明实施例还涉及所述化合物或者除草组合物在杂草防治中的用途。
通式(I)所示化合物及其可农用盐适合以异构体混合物形式和纯异构体形式用作除草剂。它们适合直接使用或适合以适当配制的组合物使用。包含通式(I)所示化合物的除草组合物非常有效地防治非作物区域的植物生长,尤其是在高施用率下。它们在作物如小麦、稻、玉米、大豆和棉花中作用于阔叶杂草和禾本科杂草而不对农作物引起任何显著的损害。该效果主要在低施用率下观察到。
在一些实施方式中,本发明实施例的通式(I)所示化合物和/或其盐适用于防治范围广泛的有害植物,例如以下属的单子叶和双子叶有害植物,这些实例仅用来说明本发明实施例,但绝不限定本发明实施例。
以下属的单子叶有害植物:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagitta ria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的双子叶有害植物:白麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、锦葵属(Anoda)、春黄菊属(Anthemis)、Aphanes属、蒿属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centa urea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、芙蓉属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、粟米草属(Mullugo)、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
在一些实施方式中,当在有害植物(禾本科杂草和/或阔叶杂草)出芽前,将本发明实施例的化合物施用于土壤表面(出苗前方法)时,可完全阻止禾本科杂草和阔叶杂草的幼苗出土,或者使它们生长至达到子叶期后停止生长,最后在经过三到四周后,彻底死亡。
在一些实施方式中,如果在出苗后将所述活性化合物施用于植物的绿色部位,则在处理后停止生长,且所述有害植物会停留在施用时间点的生长期,或在一段时间后彻底死亡,从而以此方式在极早的时间点持续地消除对作物植物有害的杂草的竞争。
尽管本发明实施例的化合物具有出色的抵抗单子叶和双子叶杂草的除草活性,但对经济上重要的作物的作物植物仅在很小程度上产生损害,或完全没有损害,取决于本发明实施例的各化合物的结构及其施用率。所述经济上重要的作物的作物植物为例如以下属的双子叶作物:落花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、芒属(Miscanthus)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia),或以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)和玉蜀黍属(Zea)。这些实例仅用来说明本发明实施例,但绝不限定本发明实施例。因此,在一些实施方式中,本发明实施例的化合物非常适用于选择性防治作物植物如农业上有用的植物或观赏植物中的不需要的植物生长。
此外,在一些实施方式中,本发明实施例的化合物(根据其具体结构和使用的施用率)对作物植物具有出色的生长调节特性。它们以调节作用参与植物自身的新陈代谢,从而可用于受控影响植物成分和促进采收,例如通过引发脱水和矮化生长。此外,它们还适于对不需要的营养生长进行一般防治和抑制,而在此过程中不会损害植物。抑制营养生长在很多单子叶和双子叶作物中起到重要作用,因为例如其可减少或完全防止倒伏。
在一些实施方式中,由于活性化合物除草和植物生长调节特性,其还可用于防治基因改性植物或通过常规诱变改性的植物的作物中的有害植物。一般而言,转基因植物的特征为特别有利的性质,例如对某些农药:特别是某些除草剂的抗性、对植物病害或植物病害病原体—如某些昆虫或微生物(如真菌、细菌或病毒)的抗性。其他具体的性质涉及例如采收物的数量、质量、贮存性、组成和具体成分。例如,具有提高的淀粉含量或改进的淀粉质量的转基因植物,或采收物含有不同脂肪酸组成的转基因植物是已知的。其他具体的性质可为对非生物胁迫因素的耐受性或抗性,例如炎热、寒冷、干旱、盐渍和紫外照射。
考虑到转基因植物,可选地,将本发明实施例式(I)的化合物和/或其盐用于有用植物和观赏植物的经济上重要的转基因作物,例如谷类(例如小麦、大麦、黑麦、燕麦、黑小麦、黍、稻、木薯和玉米),或其他作物如甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆和其他蔬菜。
可选地,式(I)的化合物作为除草剂用于对除草剂的植物毒性效应具有抗性、或通过重组技术已获得所述抗性的有用植物作物。
制备与现有植物相比具有改性特征的新植物的常规方法包括,例如常规育种方法和产生突变体。或者,可借助重组方法产生具有改变的特征的新植物。
可选地,将本发明实施例的化合物(I)用于对以下物质具有抗性的转基因作物中:生长调节剂,例如麦草畏(dicamba);或抑制植物必需酶的除草剂,所述植物必需酶例如乙酰乳酸合酶(ALS)、EPSP合成酶、谷氨酰胺合成酶(GS)或羟基苯丙酮酸双加氧酶(HPPD);或选自磺酰脲、草甘膦、草胺膦或苯甲酰基异噁唑和类似活性化合物的除草剂。
当本发明实施例的活性化合物用于转基因作物时,不仅出现在其他作物中观察到的对有害植物的效果,还常常出现对施用于具体转基因作物而言的特异性效果,例如改变的或特别拓宽的可防治杂草的范围、改进的可用于施用的施用率、可选地与转基因作物对其具有抗性的除草剂的良好结合能力以及对转基因作物植物的生长和产量的影响。
因此,本发明实施例还涉及本发明实施例的式(I)的化合物和/或其盐作为除草剂用于防治有用植物或观赏植物的作物、任选地转基因作物植物中的有害植物的用途。
在一些实施方式中,本发明实施例还涉及式(I)的化合物和/或其盐通过出苗前或出苗后方法在谷类中,例如大豆、玉米、小麦、大麦、黑麦、燕麦、黍或稻中的用途。
在一种或多种示例性的实施方式中,本发明实施例用于防治有害植物或用于植物生长调节的用途还包括其中直到施用于植物上、植物中或土壤中之后,式(I)的活性化合物或其盐才由前体物质(“前药”)形成的情况。
本发明实施例还提供了一种或多种式(I)的化合物或其盐或本发明实施例的组合物(如下文定义)(在一种方法中)用于防治有害植物或用于调节植物生长的用途,其包括将有效量的一种或多种式(I)的化合物或其盐施用于植物(有害植物,如果合适,与有用植物一起)、植物种子、植物生长的土壤中或土壤上或栽培区域。
IV.包含通式(I)的化合物和/或其盐的组合物及其配制与使用方法
本发明实施例还提供了一种除草组合物,包括所述通式(I)的化合物作为活性组分。在一些实施方式中,所述除草组合物中化合物的质量百分比为0.1%-99%,诸如0.5%-95%、1%-90%、2%-80%等。在一些实施方式中,所述除草组合物还包括安全剂。在一种或多种示例性的实施方式中,本发明实施例提供了一种除草和/或植物生长调节的组合物,其中该组合物包含:
(a)一种或多种如上定义的式(I)的化合物和/或其盐,在每种情况下如上所定义;和(b)选自(i)和/或(ii)的一种或多种其他物质:
(i)一种或多种其他农业化学活性物质,可以选自杀昆虫剂、杀螨剂、杀线虫剂、其他除草剂(即不对应于上述定义的式(I)的那些)、杀真菌剂、安全剂、肥料和/或其他生长调节剂;
(ii)一种或多种常用于作物保护的制剂助剂。
本文中,本发明实施例的组合物的组分(i)的其他农业化学活性物质可以选自在“The Pesticide Manual”,第16版,The British Crop Protection Council and theRoyalSoc.of Chemistry,2012中提及的物质。
本发明实施例的除草或植物生长调节的组合物可以包含一种、两种、三种或更多种在作物保护中常用的制剂助剂(ii),其选自表面活性剂、乳化剂、分散剂、成膜剂、增稠剂、无机盐、除尘剂、在25℃和1013毫巴下的固体载体、吸附剂颗粒状惰性材料、润湿剂、抗氧化剂、稳定剂、缓冲物质、消泡剂、水、有机溶剂、可以在25℃和1013毫巴下与水以任意比例混溶的有机溶剂。
在一些实施方式中,本发明实施例的化合物(I)可在常规制剂中以可湿性粉剂、可乳化浓缩剂、可喷雾溶液剂、粉剂或颗粒剂的形式使用。因此,本发明实施例还提供了除草和植物生长调节的组合物,其包含式(I)的化合物和/或其盐。
式(I)的化合物和/或其盐可根据所需的生物和/或物理化学参数以各种方式配制。可能的制剂包括,例如可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、可乳化浓缩剂(EC)、乳剂(EW)如水包油乳剂和油包水乳剂、可喷雾溶液剂、悬浮浓缩剂(SC)、油基或水基分散剂、油溶性溶液剂、胶囊悬浮剂(CS)、粉剂(DP)、拌种剂、用于撒播和土壤施用颗粒剂、微颗粒形式的颗粒剂(GR)、喷雾颗粒剂、吸收和吸附颗粒剂、水分散颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。
在一些实施方式中,可湿性粉剂为可均匀分散于水中的制剂,其除了含有活性化合物之外,还含有稀释剂或惰性物质,以及离子型表面活性剂和/或非离子型表面活性剂(湿润剂、分散剂),例如聚氧乙基化烷基酚、聚氧乙基化脂肪醇、聚氧乙基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2'-二萘基甲烷-6,6'-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备可湿性粉剂,在例如常规设备例如锤磨机、风磨机和空气气流粉碎机中精细研磨除草活性成分,同时或随后与制剂助剂混合。
在一些实施方式中,可乳化浓缩剂通过下述过程制备:将活性化合物溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或较高沸点的芳族化合物或烃类)或有机溶剂混合物中,并加入一种或多种离子型和/或非离子型表面活性剂(乳化剂)。可用的乳化剂的实例为:烷基芳基磺酸钙,例如十二烷基苯磺酸钙;或非离子型乳化剂,例如脂肪酸聚二醇酯类、烷基芳基聚乙二醇醚类、脂肪醇聚乙二醇醚类、环氧丙烷-环氧乙烷缩合物、烷基聚醚类、脱水山梨糖醇酯类,例如脱水山梨糖醇脂肪酸酯类或聚氧乙烯脱水山梨糖醇酯类,例如聚氧乙烯脱水山梨糖醇脂肪酸酯类。
在一些实施方式中,粉剂可通过将活性化合物与细分散的固体一起研磨而获得,所述固体例如滑石,天然粘土例如高岭土、膨润土和叶蜡石,或硅藻土。
在一些实施方式中,悬浮浓缩剂可为水基或油基的。它们可通过例如使用市售的球磨机湿法研磨,并且任选地加入例如上文在其他剂型中所列的表面活性剂而制备。
在一些实施方式中,乳剂例如水包油乳剂(EW),可例如借助搅拌器、胶体磨机和/或静态混合器使用如上文例如关于其他剂型中所列的含水有机溶剂以及任选地表面活性剂来制备。
在一些实施方式中,颗粒剂可通过将所述活性化合物喷洒在可吸附的颗粒状惰性物质上,或通过使用粘合剂(例如聚乙烯醇、聚丙烯酸钠或矿物油)将活性化合物浓缩物涂覆在载体(例如砂、高岭土或颗粒状惰性材料)表面而制备。也可将合适的活性化合物以制备肥料颗粒的常规方式制备成颗粒,如果需要,可以与肥料混合。
在一些实施方式中,水分散颗粒剂通常可通过常规方法制备,所述常规方法例如喷雾干燥法、流化床制粒法、盘式制粒法、使用高速混合器的混合法以及不使用固体惰性物质的挤出法。
在一种或多种示例性的实施方式中,本发明实施例的农业化学制剂,可选地为除草或植物生长调节的组合物,含有总量为0.1至99重量%,诸如0.5至95重量%、1至90重量%、2至80重量%的式(I)的活性化合物及其盐。
在可湿性粉剂中,活性化合物的浓度为例如约10至90重量%,至100重量%的余量由常规制剂成分组成。在可乳化浓缩剂中,活性化合物的浓度可为例如约1至90重量%、5至80重量%。粉剂形式的制剂中含有例如1至30重量%的活性组合物,通常5至20重量%的活性化合物。可喷雾溶液剂中含有例如约0.05至80重量%、2至50重量%的活性化合物。对于水分散颗粒剂而言,活性化合物的含量部分地依赖于所述活性化合物为液体形式还是固体形式,以及所使用的造粒助剂、填充剂等。在水分散颗粒剂中,活性化合物的含量为例如1至95重量%、10至80重量%。
在一些实施方式中,所提及的活性化合物制剂中任选地含有相应的常规增粘剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填充剂、载体和染料、消泡剂、蒸发抑制剂和影响pH值和粘度的试剂。制剂助剂的实例尤其记载在“Chemistry andTechnology of Agrochemical Formulations”,ed.D.A.Knowles,Kluwer AcademicPublishers(1998)中。
在一种或多种示例性的实施方式中,式(I)的化合物或其盐可原样使用或以其制剂(制剂)的形式与其他农药活性物质组合使用,例如杀昆虫剂、杀螨剂、杀线虫剂、除草剂、杀真菌剂、安全剂、肥料和/或生长调节剂,例如以成品制剂或桶混物的形式。组合制剂可基于上述制剂制备,同时考虑待组合的活性化合物的物理性质和稳定性。
在一些实施方式中,在混合物制剂或桶混物中,可与本发明实施例的式(I)的化合物组合使用的活性化合物为例如基于抑制以下酶的已知的活性化合物,所述酶为例如:乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光合体系I、光合体系II、原卟啉原氧化酶,如例如Weed Research 26(1986)441-445或"The PesticideManual",第16版,The British CropProtection Council and the Royal Soc.ofChemistry,2012及其中所引用的文献中所记载的。
特别关注的是在有用植物和观赏植物的作物中选择性地防治有害植物。尽管在许多作物中,本发明实施例的化合物(I)已具有非常好乃至足够的选择性,但原则上,在一些作物中,特别是在与其他低选择性除草剂的混合物的情况下,仍可能发生对于作物植物的植物毒性。在这方面,包含化合物(I)或其与其他除草剂或农药和安全剂的组合物的本发明实施例的化合物(I)的组合物受到特别关注。以解毒有效剂量使用的安全剂可降低例如经济上重要的作物中所使用的除草剂/农药的植物毒性副作用,所述经济上重要的作物例如谷物(小麦、大麦、黑麦、玉米、稻、黍)、甜菜、甘蔗、油菜、棉花和大豆,示例性地为谷物。
在一些实施方式中,除草剂(混合物)与安全剂的重量比通常取决于除草剂施用率和所述安全剂的功效,并且可在宽范围内变化,例如200:1至1:200、100:1至1:100、20:1至1:20。类似于化合物(I)或其混合物,安全剂可与其他除草剂/农药一起配制,并作为成品制剂或与除草剂的桶混物提供和使用。
为了使用,如果合适,以常规方式稀释市售形式的除草剂或除草剂/安全剂制剂,例如在可湿性粉剂、可乳化浓缩剂、分散剂和水分散颗粒剂的情况下使用水稀释。粉剂制剂、土壤施用颗粒剂或撒播用颗粒剂和可喷雾溶液剂通常无需在施用前用其他惰性物质进一步稀释。
式(I)的化合物和/或其盐的施用率在一定程度上受外部条件如温度、湿度等的影响。本文中,施用率可在宽范围内变化。在一些实施方式中,对于作为防治有害植物的除草剂的施用,式(I)的化合物及其盐的总量为例如0.001至10.0kg/ha、0.005至5kg/ha、0.01至1.5kg/ha、0.05至1kg/ha。这适用于出苗前和出苗后施用。
在一些实施方式中,当式(I)的化合物和/或其盐用作植物生长调节剂时,例如作为用于如上所述的那些作物植物、示例性地为谷物植物(如小麦、大麦、黑麦、黑小麦、黍、稻或玉米)的茎秆稳定剂,总施用量为例如0.001至2kg/ha、0.005至1kg/ha、10至500g/ha、20至250g/ha。这适用于出苗前和出苗后施用。
作为茎秆稳定剂的施用可在植物生长的各个阶段进行。例如在分蘖期后,在纵向生长开始时施用。
或者,作为植物生长调节剂的施用也可通过处理种子,其包括用于拌种和涂覆种子的各种技术。本文中,施用率取决于特定的技术,并且可在初步测试中确定。
在一些实施方式中,在本发明实施例的组合物(例如以混合的制剂或桶混物的形式)中,可与本发明实施例的式(I)的化合物组合使用的活性化合物为例如基于抑制下列酶的已知的活性化合物,所述酶为例如:乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光合体系I、光合体系II、原卟啉原氧化酶,如记载在例如Weed Research26(1986)441-445或"The PesticideManual",16th edition,The British CropProtection Council and the Royal Soc.of Chemistry,2012及其中所引用的文献中。
在一些实施方式中,可与本发明实施例的化合物组合的已知除草剂或植物生长调节剂为例如以下活性化合物,其中所述化合物以国际标准化组织(ISO)规定的“通用名”或以其化学名称或其代码表示。它们通常包括所有使用形式,例如酸、盐、酯以及所有异构体(例如立体异构体和旋光异构体)形式,即使未明确提及。
可以与本发明实施例的式I的化合物组合使用的已知除草剂或植物生长调节剂的实例为:
b1)选自如下的类脂生物合成抑制剂:炔草酯(clodinafop)、炔草酯(clodinafop-propargyl)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、禾草灵(diclofop-methyl)、噁唑禾草灵(fenoxaprop-ethyl)、吡氟禾草灵(fluazifop)、吡氟禾草灵(fluazifop-butyl)、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵(fluazifop-P-butyl)、精吡氟氯禾灵(haloxyfop-P)、精吡氟氯禾灵(haloxyfop-P-methyl)、噁唑酰草胺(metamifop)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、苯丙草酮;
b2)选自如下的ALS抑制剂:苄嘧磺隆(bensulfuron)、双嘧苯甲酸(bispyribac)、醚磺隆(cinosulfuron)、唑嘧磺胺酸(cloransulam)、唑嘧磺胺盐(cloransulam-methyl)、环丙磺隆(cyclosulfamuron)、唑嘧磺胺(diclosulam)、胺苯磺隆(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙氧嘧磺隆(ethoxysulfuron)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟定磺隆(flupyrsulfuron)、氟定磺隆(flupyrsulfuron-methyl-sodium)、甲酰氨磺隆(foramsulfuron)、吡氯磺隆(halosulfuron)、甲基二磺隆(mesosulfuron)、唑草磺胺(metosulam)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、烟嘧磺隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧磺隆(oxasulfuron)、五氟磺草胺(penoxsulam)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、氟丙磺隆(prosulfuron)、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、pyrimisulfan、环酯草醚(pyriftalid)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、啶咪磺隆(imazosulfuron)、碘甲磺隆钠(iodosulfuron-methyl-sodium)、甲基二磺隆(mesosulfuron)、烟嘧磺隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧磺隆(oxasulfuron)、五氟磺草胺(penoxsulam)、吡嘧磺隆(pyrazosulfuron-ethyl);
b3)选自如下的光合成抑制剂:莠灭净(ametryn)、胺唑草酮(amicarbazone)、莠去津(atrazine)、溴苯腈(bromoxynil)及其盐和酯、氯溴隆(chlorobromuron)、杀草敏(chloridazone)、草净津(cyanazine)、敌草快(diquat-dibromide)、敌草隆(diuron)、伏草隆(fluometuron)、碘苯腈(ioxynil)及其盐和酯、异丙隆(isoproturon)、环草定(lenacil)、利谷隆(linuron)、苯嗪草(metamitron)、噻唑隆(methabenzthiazuron)、扑草净(prometryn)、敌稗(propanil)、扑灭津(propazine)、pyridafol、达草止(pyridate)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、特草定(terbacil)、特丁津(terbuthylazine);
b4)选自如下的原卟啉原-IX氧化酶抑制剂:bencarbazone、双苯嘧草酮(benzfendizone)、氟丙嘧草酯(butafenacil)、吲哚酮草酯(cinidon-ethyl)、异丙吡草酯(fuazolate)、氟哒嗪草酯(flufenpyr-ethyl)、氟噁嗪酮(flumioxazin)、乙羧氟草醚(fluoroglycofen-ethyl)、氟磺胺草醚(fomesafen)、恶草灵(oxadiazon)、乙氧氟草醚(oxyfluorfen)、戊噁唑草(pentoxazone)、氟唑草胺(profuazol)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、苯嘧磺草胺(saflufenacil);
b5)选自如下的漂白剂除草剂:苯草醚(aclonifen)、氟丁酰草胺(beflubutamid)、吡草酮(benzofenap)、异恶草酮(clomazone)、吡氟草胺(diflufenican)、氟草同(fluridone)、氟啶草酮、氟咯草酮(flurochloridone)、甲基磺草酮(mesotrione)、达草灭(norflurazon)、氟吡酰草胺(picolinafen)、pyrasulfutole、吡唑特(pyrazolynate)、苄草唑(pyrazoxyfen)、磺草酮(sulcotrione)、tefuryltrione、tembotrione、苯唑草酮(topramezone)、bixlozone、三唑磺草酮、环吡氟草酮、双唑磺草酮、4-羟基-3-[[2-[(2-甲氧基乙氧基)甲基]-6-(三氟甲基)-3-吡啶基]羰基]双环[3.2.1]辛-3-烯-2-酮(H-7;
b6)选自如下的EPSP合成酶抑制剂:草甘膦、草甘膦异丙胺盐(glyphosate-isopropylammonium)和草硫膦(glyphosate-trimesium)(sulfosate);
b7)选自如下的谷氨酰胺合成酶抑制剂:双丙氨酰膦(bilanaphos(bialaphos))、双丙氨酰膦(bilanaphos-sodium)、草铵膦(glufosinate-ammonium);
b8)选自如下的DHP合成酶抑制剂:黄草灵(asulam);
b9)选自如下的有丝分裂抑制剂:氟草胺(benfluralin)、地乐胺(butralin)、氯苯胺灵(chlorpropham)、敌乐胺(dinitramine)、氟硫草定(dithiopyr)、苯胺灵(propham)、拿草特(propyzamide)、丙戊草胺(tebutam)、噻氟啶草(thiazopyr)和氟乐灵(trifluralin);
b10)选自如下的VLCFA抑制剂:乙草胺(acetochlor)、甲草胺(alachlor)、莎稗磷(anilofos)、丁草胺(butachlor)、噻吩草胺(dimethanamid)、精噻吩草胺(dimethenamid-P)、四唑酰草胺(fentrazamide)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(metolachlor-S)、烯草胺(pethoxamid)、哌草磷(piperophos)、丙草胺(pretilachlor)、扑草胺(propachlor)、异丙草胺(propisochlor)、砜吡草唑(pyroxasulfone);
b11)选自如下的纤维素生物合成抑制剂:草克乐(chlorthiamid)、敌草腈(dichlobenil)、胺草唑(flupoxam)和异恶草胺(isoxaben);
b12)选自如下的分离剂除草剂:地乐酚(dinoseb)、地乐消酚(dinoterb)以及二硝甲酚(DNOC)及其盐;
b13)选自如下的植物生长素除草剂:2,4-D及其盐和酯、2,4-DB及其盐和酯、草除灵(benazolin-ethyl)、稗草胺(clomeprop)、麦草畏(dicamba)及其盐和酯、2,4-滴丙酸(dichlorprop)及其盐和酯、高2,4-滴丙酸(dichlorprop-P)及其盐和酯、氟草烟(fluroxypyr)、氟草烟(fluroxypyr-butometyl)、氟氯胺啶(fluroxypyr-meptyl)、MCPA及其盐和酯、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB及其盐和酯、2甲4氯丙酸(mecoprop)及其盐和酯、高2甲4氯丙酸(mecoprop-P)及其盐和酯、毒莠定(picloram及其盐和酯、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、TBA(2,3,6)及其盐和酯、绿草定(triclopyr)及其盐和酯以及5,6-二氯-2-环丙基-4-嘧啶甲酸;
b14)选自如下的植物生长素输送抑制剂:二氟吡隆(diflufenzopyr)、抑草生(naptalam);
b15)选自如下的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯、棉隆(dazomet)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、敌草腈(endothal)及其盐、氟燕灵(flamprop)、氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、茚草酮(indanofan)、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、苯丙隆(methyl-dymron)、氯噁嗪草(oxaziclomefone)、壬酸(pelargonic acid)、稗草畏(pyributicarb)、和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇(H-10);
可选地,安全剂为解草酮(benoxacor)、喹氧乙酸(cloquintocet)、抑害腈(cyometrinil)、cyprosulfamide、抑害胺(dichlormid)、dicyclonone、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯噁唑酸(isoxadifen)、解草酯、吡唑解草酯、环丙磺酰胺、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(H-11;MON4660,CAS 71526-07-3)和2,2,5-三甲基-3-(二氯乙酰基)-1,3-噁唑烷(H-12;R-29148,CAS 52836-31-4)。
b1)-b15)组活性化合物和安全剂是已知的除草剂和安全剂,例如参见TheCompendium of Pesticide Common Names;(http://www.alanwood.net/pesticides/);B.Hock,C.Fedtke,R.R.Schmidt,Herbizide[除草剂],Georg Thieme Verlag,Stuttgart,1995。其他除草活性化合物由WO96/26202、WO 97/41116、WO 97/41117、WO 97/41118、WO01/83459和WO 2008/074991,W.等(编辑)"Modern CropProtectionCompounds",第1卷,Wiley VCH,2007以及其中引用的文献已知。
与现有技术相比,本发明实施例的有益效果为:
(1)本发明实施例所提供的化合物具有良好的防除有害植物活性,同时与作物植物具有良好的相容性、有效,并高效、广谱的防除禾本科杂草,还同时对作物植物具有良好的相容性。
(2)本发明实施例所提供的化合物或除草组合物,对稗草、狗尾草、马唐、反枝苋等都有很好的防效,可以用在小麦、大豆、水稻、玉米地等使用,防治各种恶性杂草。
下面通过实施例来说明式I化合物和本发明实施例的实施方案,但是本发明实施例并不限于所示实施例。
具体实施方式
以下实施例用于举例说明本发明,不应当视其为以任何方式限制本发明。
鉴于化合物的经济性与多样性,我们优选合成了一些化合物,在合成的诸多化合物中,选取部分列于下表1中。具体的化合物结构及相应的化合物信息如表1所示。表1中的化合物只是为了更好的说明本发明,但并不限定本发明,对于本领域的技术人员而言,不应将此理解为本发明上述主题的范围仅限于以下化合物。
表1
制备本发明化合物的数种方法详解说明于以下方案和实施例中。原料可以经市场购买到或者可以通过文献中已知的方法或者如详解所示进行制备。本领域技术人员应当理解,也可以利用其它合成路线合成本发明的化合物。尽管在下文中已经对合成路线中的具体原料和条件进行了说明,但是,可以很容易地将其替换为其它类似的原料及条件,这些对本发明制备方法的变型或者变体而产生的诸如化合物的各种异构等都包括在本发明范围内。另外,如下所述制备方法可以按照本发明发明实施例内容、使用本领域技术人员熟知的常规化学方法进行进一步修饰。例如,在反应过程中对适当的基团进行保护等等。
以下提供的方法实施例用于促进对本发明的制备方法的进一步了解,使用的具体物质、种类和条件确定为是对本发明的进一步说明,并不是对其合理范围的限制。在下表中表明的合成化合物中使用的试剂或者可以市场购买到,或者可以由本领域普通技术人员轻易制备得到。
代表性化合物的实施例如下,其他化合物的合成方法类似,此处不再详细说明。
合成实施例
实施例1:化合物1的制备
步骤1
将9.24克3-氨基-2-氯-4-(三氟甲氧基)苯甲酸(通过专利WO2022238178A1提供方法制得)加入250ml四口烧瓶中,依次加入5克三乙胺,100克二氯甲烷,冰浴下,慢慢滴加5.9克四氢吡喃-4-甲酰氯。滴加完毕,室温继续搅拌反应4小时,然后加入100克水洗涤,分层。有机层浓缩得目标产物11.2克。
步骤2
将180ml甲苯加入16.3g(36.7mmol)五硫化二磷中,向其中加入6.50g(61.4mmol)碳酸钠并将所得混合物在室温下搅拌5分钟。向其中加入11.2g(30mmol)2-氯-3-(四氢吡喃-4-甲酰胺基)-4-(三氟甲氧基)苯甲酸,并将所得混合物在50℃下搅拌16小时。将150ml乙酸乙酯加入反应溶液中,将所得混合物在50℃下搅拌10分钟,加入100ml水,用盐酸调pH为3-4。将该混合物转移到分液漏斗中,分层,然后有机层减压浓缩。向其中加入120ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,用100ml水洗涤两次,在60℃下减压干燥2小时,得到目标化合物。所得量为10.2g。
步骤3
将10.2克2-氯-3-(四氢吡喃-4-硫代甲酰胺基)-4-(三氟甲氧基)苯甲酸加入250ml四口烧瓶中,依次加入10克氯化亚砜,2滴DMF,100克石油醚,升温至60℃搅拌反应4小时,TLC检测,反应完毕,脱除石油醚,然后加入100克二氯甲烷,2.8克1-甲基四唑-5-胺,冰浴下,慢慢滴加3.5克三乙胺。滴加完毕,室温继续搅拌反应4小时,然后加入80克水,分层。有机层浓缩。向其中加入80ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,用80ml水洗涤两次,在60℃下减压干燥2小时,得到目标得目标产物9.8克。1H NMR(300MHz,DMSO-d6)δppm 7.45(1H,d),7.21(1H,d),4.03(3H,s),3.98-3.82(2H,m),3.58-3.40(2H,m),2.85-2.62(1H,m),1.86-1.64(4H,m)。
实施例2:化合物2的制备
将180ml甲苯加入16.3g(36.7mmol)五硫化二磷中,向其中加入6.72g(63.4mmol)碳酸钠并将所得混合物在室温下搅拌5分钟。向其中加入13.9g(31mmol)N-[2-氯-3-[(1-甲基四唑-5-基)氨甲酰基]-6-(三氟甲氧基)苯基]-四氢吡喃-4-甲酰胺(通过专利WO2022238178A1提供方法制得),并将所得混合物在50℃下搅拌19小时。将150ml乙酸乙酯加入反应溶液中,将所得混合物在50℃下搅拌10分钟,然后滤出不溶性材料,加入100克水。将该混合物转移到分液漏斗中,分层,然后减压浓缩有机层。向其中加入100ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,在60℃下减压干燥2小时,得到目标化合物。所得量为13.7g。1H NMR(300MHz,DMSO-d6)δppm7.34(1H,d),7.12(1H,d),4.03(3H,s),3.98-3.85(2H,m),3.53-3.42(2H,m),2.79-2.67(1H,m),1.86-1.68(4H,m)。
实施例3化合物3的制备
步骤1
将150ml甲苯加入16.3g(36.7mmol)五硫化二磷中,向其中加入6.72g(63.4mmol)碳酸钠并将所得混合物在室温下搅拌5分钟。向其中加入21.2g(63mmol)3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(三氟甲氧基)苯甲酰胺(通过专利WO2022238178A1提供方法制得),并将所得混合物在50℃下搅拌16小时。将150ml乙酸乙酯加入反应溶液中,将所得混合物在50℃下搅拌10分钟,然后滤出不溶性材料,加入100克水。将该混合物转移到分液漏斗中,分层,然后减压浓缩有机层。向其中加入100ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,在60℃下减压干燥2小时,得到目标化合物。所得量为20.8g。
步骤2
将17.6克3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(三氟甲氧基)硫代苯甲酰胺加入250ml四口烧瓶中,依次加入6.5克三乙胺,100克二氯甲烷,冰浴下,慢慢滴加7.8克四氢吡喃-4-甲酰氯。滴加完毕,室温继续搅拌反应4小时,然后加入100克水,分层。有机层浓缩,向其中加入100ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,在60℃下减压干燥2小时,得到目标化合物。所得量为19.75g。1H NMR(300MHz,DMSO-d6)δppm 7.24(1H,d),7.10(1H,d),4.03(3H,s),3.98-3.85(2H,m),3.53-3.42(2H,m),2.79-2.67(1H,m),1.86-1.68(4H,m)。
实施例4化合物4的制备
步骤1
将9.5克3-氨基-2-氯-4-(二氟甲氧基)苯甲酸(通过专利WO2022238178A1提供方法制得)加入250ml四口烧瓶中,依次加入5克三乙胺,100克二氯甲烷,冰浴下,慢慢滴加6.24克四氢吡喃-4-甲酰氯。滴加完毕,室温继续搅拌反应4小时,然后加入100克水洗涤,分层。有机层浓缩得目标产物12.4克。
步骤2
将150ml甲苯加入16.3g(36.7mmol)五硫化二磷中,向其中加入6.50g(61.4mmol)碳酸钠并将所得混合物在室温下搅拌5分钟。向其中加入12.4g(35mmol)2-氯-3-(四氢吡喃-4-甲酰胺基)-4-(二氟甲氧基)苯甲酸,并将所得混合物在50℃下搅拌16小时。将150ml乙酸乙酯加入反应溶液中,将所得混合物在50℃下搅拌10分钟,加入100ml水,用盐酸调pH为3-4。将该混合物转移到分液漏斗中,分层,然后有机层减压浓缩。向其中加入120ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,用100ml水洗涤两次,在60℃下减压干燥2小时,得到目标化合物。所得量为11.2g。
步骤3
将11.2克2-氯-3-(四氢吡喃-4-硫代甲酰胺基)-4-(三氟甲氧基)苯甲酸加入250ml四口烧瓶中,依次加入12克氯化亚砜,2滴DMF,100克石油醚,升温至60℃搅拌反应4小时,TLC检测,反应完毕,脱除石油醚,然后加入100克二氯甲烷,3.2克1-甲基四唑-5-胺,冰浴下,慢慢滴加5克三乙胺。滴加完毕,室温继续搅拌反应4小时,然后加入100克水,分层。有机层浓缩。向其中加入80ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,用100ml水洗涤,在60℃下减压干燥2小时,得到目标得目标产物10.8克。1H NMR(300MHz,DMSO-d6)δppm 7.74(1H,d),7.38(1H,d),7.21(1H,t),4.02(3H,s),4.00-3.84(2H,m),3.48-3.20(2H,m),2.82-2.60(1H,m),1.83-1.62(4H,m)。
实施例5化合物5的制备
步骤1
将150ml甲苯加入16.3g(36.7mmol)五硫化二磷中,向其中加入6.72g(63.4mmol)碳酸钠并将所得混合物在室温下搅拌5分钟。向其中加入20.07g(63mmol)3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(二氟甲氧基)苯甲酰胺(通过专利WO2022238178A1提供方法制得),并将所得混合物在50℃下搅拌16小时。将150ml乙酸乙酯加入反应溶液中,将所得混合物在50℃下搅拌10分钟,然后滤出不溶性材料,加入100克水。将该混合物移到分液漏斗中,分层,然后减压浓缩有机层。向其中加入100ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,在60℃下减压干燥2小时,得到目标化合物。所得量为18.8g。
步骤2
将18.8克3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(二氟甲氧基)硫代苯甲酰胺加入250ml四口烧瓶中,依次加入6.8克三乙胺,100克二氯甲烷,冰浴下,慢慢滴加8.8克四氢吡喃-4-甲酰氯。滴加完毕,室温继续搅拌反应4小时,然后加入100克水,分层。有机层浓缩,向其中加入100ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,在60℃下减压干燥2小时,得到目标化合物。所得量为22.8g。1H NMR(300MHz,DMSO-d6)δppm 7.25(1H,d),7.12(1H,d),7.21(1H,t),4.02(3H,s),4.00-3.84(2H,m),3.48-3.20(2H,m),2.82-2.60(1H,m),1.83-1.62(4H,m)。
实施例6化合物6的制备
将180ml甲苯加入16.3g(36.7mmol)五硫化二磷中,向其中加入6.72g(63.4mmol)碳酸钠并将所得混合物在室温下搅拌5分钟。向其中加入13.35g(31mmol)N-[2-氯-3-[(1-甲基四唑-5-基)氨甲酰基]-6-(二氟甲氧基)苯基]-四氢吡喃-4-甲酰胺(通过专利WO2022238178A1提供方法制得),并将所得混合物在50℃下搅拌19小时。将150ml乙酸乙酯加入反应溶液中,将所得混合物在50℃下搅拌10分钟,然后滤出不溶性材料,加入100克水。将该混合物转移到分液漏斗中,分层,然后减压浓缩有机层。向其中加入100ml水以沉淀晶体。将该混合物在室温下搅拌1小时,然后将晶体收集,在60℃下减压干燥2小时,得到目标化合物。所得量为12.85g。1H NMR(300MHz,DMSO-d6)δppm7.28(1H,d),7.15(1H,d),7.21(1H,t),4.02(3H,s),4.00-3.84(2H,m),3.48-3.20(2H,m),2.86-2.62(1H,m),1.83-1.62(4H,m)。
实施例7化合物2钠盐的制备
将24克N-[2-氯-3-[(1-甲基四唑-5-基)氨甲酰基]-6-(三氟甲氧基)苯基]-四氢吡喃-4-甲酰胺加入250ml四口烧瓶中,依次加入4.5克氢氧化钠,45克水,100克甲苯,室温搅拌反应4小时,TLC检测,反应完毕。分层。水层脱干水分得目标产物24.98克。
II.应用实施例
实施例8:出苗前除草作用
将单子叶和双子叶杂草植物或作物植物的种子置于木质纤维盆中的沙质壤土中,用土壤覆盖。然后,将实施例1-4中配制的本发明实施例的通式(I)的化合物以及对照化合物CK以水性悬浮液或乳液的形式(添加0.2%的润湿剂)以600升水/公顷(经换算)的施用率喷雾覆盖土壤的表面。处理后,将盆置于温室中,并保持在试验植物的良好生长条件下。约3周后,通过与对照组进行比较而对制剂的效果进行目测评估(以百分数计)。例如,100%活性=植物已死亡,50%除草活性或损害=植株减少至50%或植物材料减少50%,0%活性=类似于对照植物。
表2本发明实施例的通式(I)的化合物相比对照化合物的出苗前除草作用:(剂量:200g/ha)
从表2可以看出,在出苗前土壤处理之后,本发明实施例化合物的除草活性远优于对照化合物,同时与对照化合物相比本发明实施例化合物对水稻、小麦有更好的安全性。
实施例9:出苗后除草作用
将单子叶和双子叶杂草植物和作物植物的种子置于木质纤维盆中的沙质壤土中,用土壤覆盖,然后在良好生长条件下在温室中培养。播种后2至3周,在单叶阶段处理试验植物,用实施例1-4中配制的本发明实施例的通式(I)的化合物以及对照化合物CK以水性悬浮液或乳液的形式(添加0.2%的润湿剂)以600升水/公顷(经换算)的施用率喷洒到植物的绿色部分。然后将试验植物在最佳生长条件下在温室中放置约3周后,通过与对照组进行比较而对制剂的效果进行目测评估(以百分数计)。例如,100%活性=植物死亡,50%除草活性或损害=植株减少至50%或植物材料减少50%,0%活性=类似于对照植物。
表3本发明实施例通式(I)的化合物相比对照化合物的出苗后除草作用:(剂量:50g/ha)
编号 | 稗草 | 马唐 | 鳢肠 | 反枝苋 | 碎米莎草 | 水稻* |
1 | 94.7 | 96.3 | 95.8 | 100 | 90.2 | 2 |
2 | 92.4 | 94.2 | 96.5 | 98.3 | 88.4 | 0 |
3 | 93.4 | 93.8 | 94.3 | 95.2 | 89.6 | 0 |
4 | 94.2 | 94.5 | 92.8 | 100 | 90.2 | 5 |
5 | 92.6 | 90.2 | 90.5 | 94.8 | 88.2 | 5 |
6 | 95.2 | 89.2 | 93.4 | 100 | 89.6 | 0 |
CK | 89.2 | 86 | 83 | 94 | 80.8 | 10 |
注:水稻*(剂量:300g/ha)
从表3可以看出,在出苗后茎叶处理之后,本发明实施例化合物的除草活性远优于对照化合物,同时与对照化合物相比本发明实施例化合物对水稻、小麦有更好的安全性。
可见,本发明实施例的化合物无论是在出苗前还是在出苗后施用,均实现了远优于对照化合物的除草效果,同时对作物植物有良好的安全性。
本发明实施例提供了一种具有除草活性的化合物、包括该化合物的除草组合物及其用途,其具有广谱除草活性,对稗草、狗尾草、马唐、反枝苋等都有很好的防效,可以用在小麦、大豆、水稻、玉米、果园以及非耕地等使用,防治各种恶性杂草。
最后应说明的是:尽管已用具体实施例来说明和描述了本发明实施例,然而应意识到,以上各实施例仅用以说明本发明实施例的技术方案,而非对其限制;本领域的普通技术人员应当理解:在不背离本发明实施例的精神和范围的情况下,可以对前述各实施例所记载的技术方案进行修改,或者对其中部分或者全部技术特征进行等同替换;而这些修改或者替换,并不使相应技术方案的本质脱离本发明实施例各实施例技术方案的范围。
Claims (9)
2.根据权利要求1所述的新型硫代酰胺类化合物或其可农用盐,其特征在于:通式(I)中
R1选自卤代三氟甲烷基、二氟甲烷基;
R2、R3分别选自O,S;且R2、R3不同时选自O,至少有一个选自S;
R4选自甲基或乙基。
4.根据权利要求1-3任一项所述的新型硫代酰胺类化合物或其可农用盐,其特征在于,通式(I)所示的化合物的盐选自通式(I)所示的化合物的钠盐、钾盐、钙盐和锂盐中的一种,优选为钠盐、钾盐和锂盐中的一种。
5.一种根据权利要求1-4任一项所述的新型硫代酰胺类化合物或其可农用盐用于苗前或苗后茎叶处理防治杂草的应用。
6.一种除草组合物,其特征在于,包括权利要求1-4任一项所述的新型硫代酰胺类化合物或其可农用盐作为活性组分。
7.根据权利要求6所述的除草组合物,其特征在于,所述除草组合物中所述化合物的质量百分比为0.1%-99%、0.5%-95%、1%-90%或者2%-80%。
8.根据权利要求6或7所述的除草组合物,其特征在于,所述除草组合物还包括安全剂。
9.根据权利要求6所述的除草组合物,其特征在于,所述除草组合物还包括选自以下农业化学活性物质中的一种或多种:杀昆虫剂、杀螨剂、杀线虫剂、杀真菌剂、肥料、其他除草剂和其他植物生长调节剂。
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