CN113226027B - 农用烷基聚甘油胺类表面活性剂 - Google Patents
农用烷基聚甘油胺类表面活性剂 Download PDFInfo
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- CN113226027B CN113226027B CN201980084994.0A CN201980084994A CN113226027B CN 113226027 B CN113226027 B CN 113226027B CN 201980084994 A CN201980084994 A CN 201980084994A CN 113226027 B CN113226027 B CN 113226027B
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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Abstract
本发明提供了一种农用组合物,其包括至少一种农用化学品和至少一种具有结构I的烷基胺缩水甘油表面活性剂:其中R为C4‑C22直链或支链、饱和或不饱和烃基,带有或不带有侧链羟基;x为0至30,优选1至20,更优选1至10,更优选1至5;y为0至30,优选1至20,更优选1至10,更优选1至5;x+y≥2且至多为30;以及Gly为甘油残基。
Description
技术领域
总体而言,本发明涉及作为农药制剂助剂的含氮缩水甘油表面活性剂。
背景技术
在农药制剂中使用许多表面活性剂作为助剂。助剂例如可用作能够提高农药生物效力的增效剂、润湿剂、乳化剂、铺展剂、沉积助剂、漂移控制剂、水调节剂、晶体抑制剂、悬浮助剂、增稠剂或分散剂。通过添加适当的表面活性剂助剂可提高农药的生物效力。例如,众所周知,可通过含氮表面活性剂如烷基胺聚氧烯醚(烷基胺聚烷氧基化物,alkyl aminealkoxylate)表面活性剂来增强除草剂、杀真菌剂和杀虫剂的生物效力。在US4528023和US5226943中可找到含氮表面活性剂作为除草剂增效助剂的实例。US5226943还提及可通过引入某些含氮表面活性剂来提高杀真菌剂组合物的活性。在WO201280099中可找到含氮表面活性剂作为杀虫剂增效助剂的实例。在US5565409和US8097563中可找到含氮表面活性剂在杀虫剂乳液中作为乳化剂的实例。在WO201020599中可找到含氮表面活性剂在草甘膦制剂中作为增稠剂的实例。在WO2013098220中可找到含氮表面活性剂在农药乳液中作为漂移控制剂的实例。
烷基胺聚氧乙烯醚的生产要求高度的精细与技巧。烷基胺聚氧乙烯醚通过环氧乙烷与烷基胺反应制得。环氧乙烷(EO)是一种危险的气体化学品(沸点10.7℃)。它在室温下是一种易燃、刺激性及麻醉性气体。鉴于其挥发性,通常以冷冻液体形式对EO进行处理与运输,以降低火灾或爆炸的风险。这增加了运输与存储的成本。由于EO的危险性,烷基胺聚氧乙烯醚的生产要求对反应器进行特殊设计,需要具有进气管的加压反应器。
尽管烷基胺聚氧乙烯醚难以制备,但仍是农药制剂中最常用的助剂之一。烷基胺聚氧乙烯醚分子包含亲水部分(具有不同EO单元的叔氮)和疏水部分(烃基),如以下结构通式所示:
其中R为不同链长的烃基(即疏水部分),x和y可采取不同值。正是这种分子结构产生了在农业应用中作为助剂的效用。众所周知,可通过改变烃链长度和EO单元数量来改变烷基胺聚氧乙烯醚的物理性质,以适应各种应用需求。
烷基胺聚氧乙烯醚的已知应用之一是在草甘膦除草剂中作为增效助剂。本领域已知,在烷基胺聚氧乙烯醚族系中,具有更长烃链长度(C18左右或更长)和更多EO单元数(多于10左右)的烷基胺聚氧乙烯醚对草甘膦而言更为有效。使用高负载草甘膦制剂[例如,水中含540g/l ae(酸当量)草甘膦]以尽可能地减少运输成本和存储成本也是一种常见做法,因为高负载制剂携带的水较少。有效制剂要求足量的助剂,通常在制剂中大于约10%。然而,碳链长度长(大于等于C18左右)且EO单元不少于5左右的烷基胺聚氧乙烯醚可能在高负载制剂中不相容,导致浊点低(随着温度升高,样品从澄清变浑浊的温度)并最终造成相分离。为了能够在高负载制剂中含有足量的有效烷基胺聚氧乙烯醚助剂,通常必须使用增溶剂或相容剂(WO2010036996)。然而,增溶剂或相容剂对生物功效增强效果没有明显贡献,并且它们的使用增加了制剂的总成本。
对于生产可用于农业应用的烷基胺衍生物而言,具有不同链长的烃易于获得,但除环氧乙烷以外的亲水基团的选择有限。期望获得在农业应用中与烷基胺聚氧乙烯醚表现类似,而且(1)处理组分时危险性较小、(2)制备条件较容易、及(3)在高负载农药制剂中具有较好相容性的烷基胺衍生物。本发明的主题提供了这些超出本领域目前已知者的优势。
概述
总体而言,本发明涉及含氮表面活性剂,即烷基聚甘油胺(或缩水甘油烷基胺)表面活性剂,其通过烷基胺与缩水甘油反应获得。意想不到的是,本发明的烷基聚甘油胺表面活性剂在高负载农用制剂中具有比烷基胺聚氧乙烯醚更好的相容性,而无需相容剂。特别是,本发明的烷基聚甘油胺表面活性剂在含有诸如2,4-滴盐、麦草畏盐、草甘膦盐和草铵膦盐等除草剂的高负载除草制剂中相容,而无需增溶剂(相容剂),并可在农药制剂中用作(共)乳化剂。
通过烷基胺与缩水甘油反应获得的烷基聚甘油胺是超越烷基胺聚氧乙烯醚的一种进步。缩水甘油为液体,根据各政府机构的分类,其危险性低于环氧乙烷。因而,相比于EO的处理和烷基胺聚氧乙烯醚的制备,缩水甘油的处理和烷基聚甘油胺的制备更为容易。
在一种实施方式中,本发明为一种农用组合物,该组合物包括至少一种农用化学品和至少一种选自以下通式结构(I)的烷基聚甘油胺表面活性剂:
其中R为C4-C22直链或支链、饱和或不饱和烃基,带有或不带有侧链羟基;x为0至100,优选1至20,更优选1至10,更优选1至5;y为0至100,优选1至20,更优选1至10,更优选1至5;及x+y≥2。在不同的实施方式中,x为0至30且y为0至30,其中x+y≥2且至多为30。在其它实施方式中,x为0至30且y为0至30,其中x+y≥3且至多为30。
Gly为甘油残基。x或y大于1时形成的聚甘油基部分可为直链或支链。直链聚甘油基部分可具有以下式(II)。
支链聚甘油基部分可具有以下式(III)。
在一些实施方式中,聚甘油基部分可同时包含支链和直链链段两者。
在另一实施方式中,本发明为一种农药组合物,该组合物包括至少一种农药和至少一种具有结构(I)的烷基聚甘油胺表面活性剂。
在又一实施方式中,本发明为一种组合物,该组合物包括结构(I)的烷基聚甘油胺表面活性剂和选自水、二醇类或液体烷氧基化醇的稀释剂。
附图说明
以下将结合附图对本发明进行说明,其中图1示出了实施例9的生物效力研究结果。
详述
本发明的烷基聚甘油胺表面活性剂具有以下通式结构(I):
其中R为C4-C22直链或支链、饱和或不饱和烃基,带有或不带有侧链羟基;x为0至100,优选1至20,更优选1至10,更优选1至5;y为0至100,优选1至20,更优选1至10,更优选1至5;并且x+y≥2。在一种实施方式中,R为C16-C18。在一种实施方式中,R为C12-C16。在一种实施方式中,R为来源于牛脂、椰油、油基及其组合的烃基。在不同的实施方式中,x为0至30且y为0至30,其中x+y≥2且至多为30。在其它实施方式中,x为0至30且y为0至30,其中x+y≥3且至多为30。在这些实施方式中,所述烷基胺缩水甘油表面活性剂可表述为烷基胺聚缩水甘油表面活性剂。在各种非限制性实施方式中,明确规定,所有数值和数值范围,包括上述数值和介于上述数值范围之间的数值,在本文中明确规定予以采用。可预想到这些表面活性剂中的两种或更多种可组合在一起形成表面活性剂组合物。
Gly为甘油残基。x或y大于1时形成的聚甘油基部分可为直链或支链。直链聚甘油基部分可具有以下通式(II)。
支链聚甘油基部分可具有以下式(III)。
所述聚甘油基部分的增长可借助于甘油残基的末端伯羟基(形成直链链段),或借助于甘油残基的非末端仲羟基(形成支链链段)。
在另一些其它实施方式中,如本领域技术人员所理解的,所述表面活性剂可进一步限定为大豆烷基胺类聚甘油胺。例如,众所周知,大豆油的典型成分如下:
大豆油:14%饱和脂肪酸;81%不饱和脂肪酸
% 脂肪酸组成
10 棕榈酸16∶0饱和C16
4 硬脂酸18∶0饱和C18
23 油酸18∶1n-9单不饱和C18
51 亚油酸18∶2n-6二元不饱和C18
7 亚麻酸18∶3n-3三元不饱和C18
因而,可预想到上述“R”基团可反映、作为或代表大豆油这些取代基中的一个或多个。例如,R可由棕榈酸部分、硬脂酸部分、油酸部分、亚油酸部分、亚麻酸部分或其组合形成或从中选择。或者,所述R基团可表述为选自上述之中任何一种或多种的脂肪基团。甚至还可形成不同大豆烷基胺类聚甘油胺的组合,其中各自均包含一种或多种上述基团。
如本文所用,农用化学品是用于农业制剂的化学品。农用化学品的非限制性实例包括肥料、微量营养素、活化剂助剂或增效剂、漂移控制剂、乳化剂、沉积助剂、水调节剂、润湿剂、分散剂、相容剂、悬浮助剂、农药(例如除草剂、杀真菌剂和杀虫剂)、以及生长抑制剂。
本发明的一种实施方式为包含本发明所述烷基聚甘油胺表面活性剂的除草制剂。适宜的除草剂包括但不限于乙草胺、三氟羧草醚、苯草醚、甲草胺、莠灭净、酰嘧磺隆、氯氨吡啶酸、氨基三唑、莎稗磷、黄草灵、莠去津、唑啶草酮、四唑嘧磺隆、草除灵、氟草胺、苄嘧磺隆、苯达松、甲羧除草醚、双丙氨膦、双草醚、除草定、丁草胺、丁苯草酮、苯酮唑、长杀草、唑酮草酯、氯草敏、氯嘧磺隆、氯溴隆、绿麦隆、氯磺隆、吲哚酮草酯、醚磺隆、烯草酮、异噁草松、二氯吡啶酸、氯酯磺草胺、氯磺隆、氰草津、草灭特、环丙嘧磺隆、噻草酮、茅草枯、甜菜胺、麦草畏、敌草腈、二氯丙烯胺、双氯磺草胺、吡氟草胺、噁唑隆、哌草丹(dimepipeate)、二甲草胺、二甲吩草胺、敌草快、敌草隆、戊草丹、乙丁烯氟灵、甲磺隆、乙氧呋草黄、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、氟消草、氟噻草胺、唑嘧磺草胺、丙炔氟草胺、伏草隆、氟啶嘧磺隆、氟咯草酮、氟草定、呋草酮、氟磺胺草醚、酰胺磺隆、草铵膦、环嗪酮、咪草酸、咪草啶酸、甲基咪草烟、灭草烟、灭草喹、咪草烟、唑吡嘧磺隆、碘磺隆、碘苯腈、异丙隆、异噁酰草胺、异噁唑草酮、乳氟禾草灵、环草定、利谷隆、苯噻草胺、甲基二磺隆、硝磺草酮、苯嗪草酮、吡唑草胺、甲基苯噻隆、溴谷隆、异丙甲草胺、磺草胺唑、甲氧隆、嗪草酮、甲磺隆、禾草敌、MSMA、敌草胺、烟嘧磺隆、达草呋、胺磺灵、丙炔噁草酮、噁草酮、环氧嘧磺隆、乙氧氟草醚、百草枯、二甲戊灵、甜菜宁毒莠定、丙草胺、环苯草酮、扑草净、敌稗、异丙草胺、丙苯磺隆、戊炔草胺、苄草丹、氟磺隆、吡草醚、吡嘧磺隆、哒草特、嘧草硫醚、二氯喹啉酸、氯甲喹啉酸、砜嘧磺隆、烯禾啶、西玛津、精异丙甲草胺、磺草酮、甲磺草胺、磺酰磺隆、丁噻隆、吡喃草酮、特丁津、特丁净、噻吩磺隆、禾草丹、肟草酮、野麦畏、醚苯磺隆、苯磺隆、绿草定、三氟啶磺隆、氟乐灵、氟胺磺隆、三氟甲磺隆及其混合物和组合。优选的除草剂为乙草胺、莠去津、麦草畏、草铵膦、百草枯、草甘膦、2,4-滴及其混合物和组合。更优选的除草剂是2,4-滴、莠去津、麦草畏、草甘膦、草铵膦及其混合物和组合。最优选的除草剂是草甘膦和草铵膦。在所述除草剂为酸的情况下,可以酸的形式使用,但优选所述除草剂为选自胺盐、锂盐、钠盐、铵盐或钾盐中至少一种的盐的形式。应当指出的是,当农药作为通用名称出现在正文中而未指明抗衡离子时,在整个说明书中均指其酸的形式和盐的形式。
本发明的另一实施方式为包含本发明所述烷基聚甘油胺表面活性剂的杀真菌制剂。适宜杀真菌剂的实例包括但不限于,苯并噻二唑、二甲基吗啉、吲唑磺菌胺、敌菌灵、氧环唑、嘧菌酯、苯霜灵、麦锈灵、苯菌灵、苯噻菌胺、乐杀螨、联苯、联苯三唑醇、灭瘟素、啶酰菌胺、糠菌唑、乙嘧酚磺酸酯、敌菌丹、克菌丹、多菌灵、萎锈灵、环丙酰菌胺、地茂丹、百菌清、乙菌利、铜、氰唑磺菌胺、环氟菌胺、霜脲氰、环唑醇、嘧菌磺胺、苯磺菌胺、双氯氰菌胺、哒菌酮、氯硝胺、乙霉威、苯醚甲环唑、氟嘧菌胺、二甲嘧酚、烯酰吗啉、醚菌胺、烯唑醇、敌螨普、二噻农、十二环吗啉、多果定、敌瘟磷、烯肟菌酯、氟环唑、乙环唑、噻唑菌胺、乙嘧酚、氯唑灵、噁唑菌酮、咪唑菌酮、氯苯嘧啶醇、腈苯唑、甲呋酰胺、环酰菌胺、氰菌胺、拌种咯、苯锈啶、丁苯吗啉、三苯基乙酸锡、三苯基氯化锡、三苯基氢氧化锡、福美铁、嘧菌腙、氟啶胺、咯菌腈、氟吗啉、氟吡菌胺、氟嘧菌酯、氟喹唑、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、三乙膦酸铝、四氯苯酞、麦穗宁、呋霜灵、呋吡菌胺、双辛胍胺、己唑醇、恶霉灵、抑霉唑、亚胺唑、双胍辛胺、碘代丙炔基正丁氨基甲酸酯(iodocarb)、种菌唑、异稻瘟净(IBP)、异菌脲、缬霉威、稻瘟灵、异噻菌胺、春雷霉素、醚菌酯、昆布多糖、代森锰锌、双炔酰菌胺、代森锰、生物材料、嘧菌胺、灭锈胺、敌螨普、甲霜灵、精甲霜灵、叶菌唑、磺菌威、代森联、苯氧菌胺、苯菌酮、矿物油、植物精油、腈菌唑、萘替芬、氟苯嘧啶醇、辛噻酮、呋酰胺、origin、肟醚菌胺、恶霜灵、恶喹酸、恶咪唑、氧化萎锈灵、土霉素、稻瘟酯、戊菌唑、戊菌隆、吡噻菌胺、亚磷酸、啶氧菌酯、哌丙灵、多抗霉素、碳酸氢钾、烯丙苯噻唑、咪鲜胺、腐霉利、霜霉威、丙环唑、丙森锌、丙氧喹啉、硫菌威、丙硫菌唑、吡唑醚菌酯、吡菌磷、吡菌苯威、稗草畏、啶斑肟、嘧霉胺、咯喹酮、喹氧灵、五氯硝基苯(PCNB)、盐类、硅噻菌胺、硅氟唑、螺环菌胺、链霉素、硫磺、戊唑醇、叶枯酞、四氯硝基苯(TCNB)、特比萘芬、四氟醚唑、噻菌灵、噻呋酰胺、硫菌灵、甲基硫菌灵、福美双、噻酰菌胺、甲基立枯磷、甲苯氟磺胺、三唑酮、三唑醇、咪唑嗪、三环唑、十三吗啉、肟菌酯、氟菌唑、嗪氨灵、灭菌唑、井冈霉素、霜霉灭、乙烯菌核利、代森锌、福美锌、苯酰菌胺及其混合物和组合。
本发明的另一实施方式为包含本发明所述烷基胺缩水甘油表面活性剂的杀虫制剂。适宜杀虫剂的实例包括但不限于,煤油或硼砂、植物性治疗药物或天然有机化合物(尼古丁、除虫菊酯、士的宁和鱼藤酮)、氯化烃(DDT、林丹、氯丹)、有机磷酸盐(马拉硫磷和二嗪农)、氨基甲酸酯(甲萘威和残杀威)、熏蒸剂(萘)和苯(樟脑丸)、合成拟除虫菊酯及其混合物和组合。
本发明的一种实施方式为一种表面活性剂组合物,其包括结构(I)的烷基聚甘油胺和稀释剂,其中所述烷基聚甘油胺的浓度为约30-90%,优选为40-80%,或更优选为50-75%。优选地,所述稀释剂选自水、二醇类、液体烷氧基化醇或其组合。
本发明的又一实施方式为一种混合物,该混合物包含选自以上所述的任意除草剂、杀真菌剂和杀虫剂并且还包含本发明的一种或多种烷基聚甘油胺表面活性剂。
本发明的烷基聚甘油胺表面活性剂可以桶混添加剂形式使用或在罐装制剂中配制。所述表面活性剂适用于固体农药制剂,尤其适用于液体农药制剂。
本发明的制剂中可存在的其它添加剂有消泡剂、稀释剂、相容剂、生物杀灭剂、增稠剂、漂移控制剂、染料、香料和螯合剂。由于烷基聚甘油胺表面活性剂在高负载农药制剂中具有高相容性,因而可能无需使用相容剂。
在罐装农药制剂中本发明所述烷基聚甘油胺表面活性剂的使用浓度可为约0.005%至约30%,优选约0.05%至约20%,更优选约0.5%至约15%(以重量%计)。基于活性成分的重量%,农药浓度为约5%至65%,优选10%至60%,更优选30%至55%,进一步更优选40%至55%。
本发明的烷基聚甘油胺表面活性剂在桶混农药喷雾溶液中的使用浓度可占整个喷雾溶液的约0.001%至约5%,优选约0.01%至约2%,更优选约0.1%至约1%(以表面活性剂的重量百分比计)。
此外,披露了一种使用本发明所述组合物防治植物或植被病害的方法。该方法包括将有效量的所述农用组合物施用于植物(特别是作物)以杀灭或防治害虫。使上述农用组合物与害虫接触。所述农用组合物可以上述形式使用或者用水或适宜的稀释剂进行稀释。
所有单位均为重量百分比(即,wt%)。
本发明的表面活性剂还可与其它表面活性剂一同使用,例如烷基胺聚氧烯醚及其季铵盐、阴离子表面活性剂(如烷基或醚硫酸盐、烷基或芳基磺酸盐、磷酸酯和乙氧基化磷酸酯)、非离子表面活性剂(如烷氧基化醇、烷基(C6-C18)多糖苷)、两性表面活性剂、季铵盐表面活性剂和有机硅表面活性剂。
在其它实施方式中,本发明提供了一种农用组合物,其包含至少一种农用化学品和至少一种结构I的烷基胺缩水甘油表面活性剂:
其中R为C4-C22直链或支链、饱和或不饱和烃基,带有或不带有侧链羟基;x为0至30,优选1至20,更优选1至10,更优选1至5;y为0至30,优选1至20,更优选1至10,更优选1至5;x+y≥2且至多为30,以及Gly为甘油残基。
在一种实施方式中,x+y≥3且至多为30。
在另一实施方式中,x+y为5至20。
在另一实施方式中,x+y为2至10。
在另一实施方式中,x和/或y大于1,使得所述聚甘油基部分为直链、支链或具有直链链段和支链链段两者。
在另一实施方式中,所述农用化学品为农药、除草剂、杀真菌剂或杀虫剂。
在另一实施方式中,所述农用化学品为有机磷除草剂,优选草甘膦或草铵膦。
在另一实施方式中,所述农用化学品为生长素除草剂,优选麦草畏或2,4-滴。
在另一实施方式中,所述农用化学品为康唑类杀真菌剂,优选三唑类杀真菌剂,更优选戊唑醇。
在另一实施方式中,所述农用化学品为拟除虫菊类杀虫剂,优选拟除虫菊酯类杀虫剂。
在另一实施方式中,所述拟除虫菊酯类杀虫剂为联苯菊酯。
在另一实施方式中,R为C16-C18。
在另一实施方式中,R为C12-C16。
在另一实施方式中,R为来源于牛脂、椰油、油基及其组合的烃基。
在不同的实施方式中,x为0至30且y为0至30,其中x+y≥2且至多为30。在其它实施方式中,x为0至30且y为0至30,其中x+y≥3且至多为30。在这些实施方式中,所述烷基胺缩水甘油表面活性剂可表述为烷基胺聚缩水甘油表面活性剂。在各种非限制性实施方式中,明确规定,所有数值和数值范围,包括上述数值和介于上述数值范围之间的数值,在本文中明确规定予以采用。可预想到这些表面活性剂中的两种或更多种可组合在一起形成表面活性剂组合物。
本发明还提供了一种防治植被病害的方法,其中该方法包括将有效量的上述农用组合物施用于植被。
除所述农用组合物以外,本发明还涉及表面活性剂本身,即上述表面活性剂的任意实施方式。
提供以下非限制性实施例,以对本发明进行进一步地说明和解释。
实施例
实施例1.烷基聚甘油胺表面活性剂的合成
所用原料
所用缩写
“T”代表“牛油胺”,“O”代表油胺,“C”代表“椰油胺”,G代表甘油单元。例如:
T-5G(即牛油胺5G)是指具有5个甘油单元的牛油胺。
O-6G(即油胺6G)是指具有6个甘油单元的油胺。
C-2G(即椰油胺2G)是指具有2个甘油单元的椰油胺。
表1.合成/化合物实例
样品# | 说明(胺+近似理论平均值个甘油单元) |
1 | 牛脂胺-5G T-5G |
2 | 牛脂胺-10G T-10G |
3 | 油胺-6G O-6G |
4 | 油胺-8G O-8G |
5 | 油胺-10G O-10G |
6 | 椰油烷基胺-2G C-2G |
7 | 椰油烷基胺-4.4G C-4.4G |
8 | 油胺-20G O-20G |
合成工序
采用以下工序制备了样品#1,采用类似工艺合成了其它样品,并适当调整了相关脂肪酸胺和缩水甘油的摩尔比(如下所讨论的)。
历经3小时将缩水甘油(44.4g,0.6mol)逐滴加入到在氮气气氛下在圆底烧瓶中进行搅拌的牛油胺(32.04g,0.12mol)中,使反应混合物的温度保持在80至120℃之间。在约110-120℃下将所述反应混合物进一步搅拌约1小时,直至IR分析显示840cm-1附近不再有缩水甘油引起的环氧化物峰。收集由此获得的澄清的浅棕色粘稠液体产物。
可任选通过添加必要量的水或其它溶剂/稀释剂来进一步稀释由此获得的产物。
对于样品#2至#8,按照与缩水甘油的相关摩尔比使用所指定的胺重复样品#1的工艺过程。例如,对于样品#2,采用1∶10的牛油胺与缩水甘油摩尔比,重复样品#1的工艺过程,对于样品#3,采用1∶6的油胺与缩水甘油摩尔比,对于样品#4,采用1∶8的油胺与缩水甘油摩尔比,等等。
可预料到的是,在最终产物中会形成副产物,例如聚甘油。在此描述的和在随后的实施例中描述的样品无需进一步提纯即可使用。
实施例2.稀释的烷基聚甘油胺组合物
一些烷基聚甘油胺样品(活性成分加上诸如聚甘油等副产物)为蜂蜜状(非常高的粘度),难以处理。此外,这些产物在加入水(或水溶液)中时会形成硬凝胶,所述凝胶会花费较长时间来溶解。这些表面活性剂在实际使用中可转化为易于处理的产物。发现了几种稀释剂可有效降低产物的粘度并最大限度地降低凝胶形成的可能性。实例如表2所示。
表2.稀释剂对凝胶形成的影响
如表2所示,可对本发明的烷基聚甘油胺表面活性剂进行稀释以改善处理和使用性。
实施例3.水性高负载农药制剂中的烷基聚甘油胺
在表3中可获知各种烷基聚甘油胺表面活性剂与对比例在高负载农药制剂中的相容性。
高负载农药制剂具有运输水量较少和运输容器用料较少的优势。然而,高负载制剂会难以引入功效所需的助剂量,因为高负载制剂常在储存温度超过55℃时发生分离。通常,为达到合格的功效,制剂中的助剂量优选为至少8重量%。
表3.各种烷基聚甘油胺与对比例在高负载农药制剂中的相容性
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*:对比例
**:Emulpon CO-360为蓖麻油聚氧乙烯醚,一种众所周知的乳化剂。
结果表明,与基于烷基胺聚氧乙烯醚的对应物相比,表3中的烷基聚甘油胺在高负载农药制剂中具有更好的相容性。在一些情况下(例如样品3.26、3.27),它们甚至可起到增溶剂的作用(帮助溶解更多不相容成分的能力)。在其它情况下(3.22),烷基聚甘油胺显示出乳化能力。
实施例4.戊唑醇杀真菌乳油制剂中乳化剂(烷基聚甘油胺/烷基EO-PO嵌段共聚物)之间乳化性能的协同作用
本领域公知通常需要三种乳化剂一同作用来形成良好的乳油(emulsifierconcentrate)(EC)。在一些情况下,可能仅需两种乳化剂。在极少数情况下,一种乳化剂即足以。EC的性能取决于乳化剂的正确选择和乳化剂的浓度。
为了对本发明所述的烷基聚甘油胺表面活性剂作为乳化剂的可能性进行评估,按照不同比例混合了含有O-8G的两种戊唑醇乳油(EC-1和EC-2)。通过在8打兰(dram)的小瓶中将1g EC加入到19g水中(稀释5%)中并翻转10次获得乳液。按照4个等级评价乳化起霜(bloom)(即加入水中后立即形成白色云状物的能力)和乳化质量:优、良、可(一般)和差。乳化性能结果如表4所示。
EC-1:15%O-8G+85%戊唑醇预混物(30%戊唑醇于70%Armid DM-10C10二甲酰胺中)
EC-2*:15%Ethylan NS-500LQ(烷基EO-PO嵌段共聚物)+85%戊唑醇预混物(30%戊唑醇于70%Armid DM-10中)
Ethylan NS-500LQ,一种丁基EO/PO共聚物,是一种众所周知的乳化剂。Armid DM-10是一种众所周知的亲水性溶剂。EC-1包含本发明的O-8G烷基聚甘油胺。EC-2*为对比例。
表4.戊唑醇杀真菌乳油制剂中乳化剂(烷基聚甘油胺/烷基EO-PO嵌段共聚物)之间乳化性能的协同作用
表4的结果表明O-8G具有在戊唑醇杀真菌剂EC中作为(共)乳化剂的可能。
实施例5.戊唑醇杀真菌乳油制剂中乳化剂(烷基聚甘油胺/烷基EO-PO嵌段共聚物/Ca DDBS)之间乳化性能的协同作用
三种戊唑醇乳油EC-1、EC-2和EC-3以不同比例混合。通过在8打兰的小瓶中将1gEC加入到19g水(稀释5%)中并翻转10次来获得乳液。按照4个等级评价起霜和乳化质量:优、良、可(一般)和差。乳化性能结果如表5所示。
EC-1和EC-2与实施例4中的相同。
EC-3*:15%Witconate P-1220EH(60%Ca DDBS)+85%戊唑醇预混物(30%戊唑醇于70%Armid DM-10之中)
Witconate P-1220EH是一种众所周知的乳化剂,含有约60%的十二烷基苯磺酸钙。
表5.戊唑醇杀真菌乳油制剂中乳化剂(烷基聚甘油胺/烷基EO-PO嵌段共聚物/CaDDBS)之间乳化性能的协同作用
表5的结果再次表明烷基聚甘油胺表面活性剂(例如O-8G)具有在戊唑醇杀真菌剂EC中作为(共)乳化剂的可能性。
实施例6.联苯菊酯杀虫剂乳油制剂中乳化剂(烷基聚甘油胺和烷基EO-PO嵌段共聚物)之间乳化性能的协同作用。
两种联苯菊酯乳油EC-4和EC-5以不同比例混合。通过在8打兰的小瓶中将1g EC加入到19g水中(稀释5%)并翻转10次来获得乳液。按照4个等级评价起霜和乳化质量:优、良、可(一般)和差。乳化性能结果如表6所示。
EC-4:8.1%O-10G+91.9%联苯菊酯预混物(10%联苯菊酯+40%芳香族200+50%Armid DM-10)
EC-5*:8.1%Ethylan NS-500LQ+91.9%联苯菊酯预混物(10%联苯菊酯+40%芳香族200+50%Armid DM-10)
表6.杀虫剂乳油制剂中乳化剂(烷基聚甘油胺和烷基EO-PO嵌段共聚物)之间乳化性能的协同作用。
表6的结果表明烷基聚甘油胺表面活性剂(例如O-10G)具有在联苯菊酯杀虫剂EC中作为(共)乳化剂的可能性。
实施例7.杀虫剂乳油制剂中乳化剂(烷基聚甘油胺/烷基EO-PO嵌段共聚物/Ca-DDBS)之间乳化性能的协同作用
三种乳油EC-4、EC-5和EC-6以不同比例混合。通过在8打兰的小瓶中将1g EC加入到19g水中(稀释5%)并翻转10次获得乳液。按照4个等级评价起霜和乳化质量:优、良、可(一般)和差。乳化性能结果如表7所示。
EC-4和EC-5与实施例6中的相同。
EC-6*:8.1%Witconate P-1220EH(60%Ca DDBS)+91.9%联苯菊酯预混物(10%联苯菊酯+40%Aromatic 200+50%Aramid DM-10)。
表7.杀虫剂乳油制剂中乳化剂(烷基胺缩水甘油/烷基EO-PO嵌段共聚物/CaDDBS)之间乳化性能的协同作用
表7的结果再次表明烷基聚甘油胺表面活性剂(例如O-10G)具有在联苯菊酯杀虫剂EC中作为(共)乳化剂的可能性。
实施例8.烷基聚甘油胺表面活性剂形成微乳液的能力
制备了以下微乳液:
表8的结果表明烷基聚甘油胺表面活性剂(例如O-10G)可用于形成微乳液。
实施例9.防治2周后在温室试验中使用和不使用烷基聚甘油胺表面活性剂的IPA-草甘膦的生物功效
在此实施例中,Ethomeen T/25牛脂胺聚氧乙烯醚,一种农药制剂中众所周知的助剂,用作阳性对照。仅草甘膦样品用作阴性对照。以三种速率喷洒小麦(模型植物):150gae/H、300g ae/H和600g ae/H。评级是在防治2周后(WAT)获得的。如图1所示的生物效力结果表明,以T-5G、T-10G、C-2G和O-8G为例的烷基聚甘油胺比单独使用草甘膦的样品具有更好的杂草控制性能。T-5G、T-10G、C-2G和O-8G的性能与Ethomeen T/25相当。
明确规定,在各种非限制性实施方式中,上述组分、组合物、方法步骤和各种替代方案选项的所有组合在本文中均考虑在内予以采用,尽管未在同一段落中描述或在上述单个实施方式中明显相互关联。
尽管在前述详细说明中已给出了至少一个示例性实施方式,但应当理解还存在大量变型。此外还应当理解的是,一个或多个示例性实施方式仅为示例,不旨在以任何方式限制范围、适用性或配置。相反,前述详细说明将为本领域技术人员实现示例性实施方式提供方便的指引。应当理解,在不脱离所附权利要求所示范围的情况下,可对示例性实施方式中所述要素的功能和设置作出各种改变。
Claims (17)
1.一种高负载的农用组合物,其包括:
至少一种农用化学品,
至少一种具有结构I的烷基胺缩水甘油表面活性剂:
其中R为C4-C22直链或支链、饱和或不饱和烃基,带有或不带有侧链羟基;x为0至30;y为0至30;x+y≥2且至多为30;以及Gly为甘油残基;和
至少一种烷基EO-PO嵌段共聚物,其中EO是氧化乙烯,PO是氧化丙烯,
其中所述农用化学品为选自有机磷除草剂、生长素除草剂的除草剂,选自康唑类和三唑类的杀真菌剂,或拟除虫菊杀虫剂,
其中所述有机磷除草剂选自草甘膦或草铵膦,
其中所述生长素除草剂选自麦草畏或2,4-滴,
其中所述三唑类杀真菌剂选自戊唑醇,以及
其中所述拟除虫菊杀虫剂选自拟除虫菊酯杀虫剂。
2.根据权利要求1所述的农用组合物,其中x为1至20。
3.根据权利要求1所述的农用组合物,其中x为1至10。
4.根据权利要求1所述的农用组合物,其中x为1至5。
5.根据权利要求1所述的农用组合物,其中y为1至20。
6.根据权利要求1所述的农用组合物,其中y为1至10。
7.根据权利要求1所述的农用组合物,其中y为1至5。
8.根据权利要求1所述的农用组合物,其中x+y≥3且至多为30。
9.根据权利要求1所述的农用组合物,其中x+y为5-20。
10.根据权利要求1所述的农用组合物,其中x+y为2-10。
11.根据权利要求1-10中任一项所述的农用组合物,其中x和/或y大于1,使得聚甘油基部分为直链、支链或具有直链链段和支链链段两者。
12.根据权利要求1所述的农用组合物,其中所述拟除虫菊酯杀虫剂为联苯菊酯。
13.根据权利要求1-10中任一项所述的农用组合物,其中R为C16-C18。
14.根据权利要求1-10中任一项所述的农用组合物,其中R为C12-C16。
15.根据权利要求1-10中任一项所述的农用组合物,其中R为来源于牛脂、椰油、油基及其组合的烃基。
16.根据权利要求1-10中任一项所述的农用组合物,其中所述烷基EO-PO嵌段共聚物为丁基EO-PO嵌段共聚物。
17.一种防治植被病害的方法,其中该方法包括将有效量的权利要求1-16中任一项所述的农用组合物施用于植被。
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