CN101702873B - 微乳剂和它们在提高杀虫剂的生物学效力中的应用 - Google Patents
微乳剂和它们在提高杀虫剂的生物学效力中的应用 Download PDFInfo
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- CN101702873B CN101702873B CN2007800531009A CN200780053100A CN101702873B CN 101702873 B CN101702873 B CN 101702873B CN 2007800531009 A CN2007800531009 A CN 2007800531009A CN 200780053100 A CN200780053100 A CN 200780053100A CN 101702873 B CN101702873 B CN 101702873B
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Abstract
用于农业的微乳剂形式的均匀而稳定辅助剂包含：a)表面活性剂的混合物，该混合物含有i)一种或多种烷基聚糖苷的阴离子衍生物；ii)一种或多种烷基聚糖苷；iii)一种或多种脂肪醇的阴离子衍生物；b)一种或多种衍生自植物油酯交换反应的脂肪酸甲基酯、一种或多种植物油、或它们的混合物；c)一种或多种非离子型表面活性剂；d)水。
Description
技术领域
本发明涉及用于农业的均匀且稳定的微乳剂形式辅助剂，例如作为水性喷雾剂应用的苗期使用(postemergence)除草剂和/或叶片处理杀真菌剂的罐内混合添加剂(tank-mix additive)。
本发明辅助剂的组分以低剂量协同作用以增强喷雾保留性，它们在喷雾沉积物中提供亲脂性和亲水性环境，从而增强除草剂和/或杀真菌剂的叶片渗透性和效力。
本发明辅助剂可作为单一稳定制剂提供，从而减少向喷雾剂罐内混合物添加独立组分的需求。
背景技术
大量矿物油和植物油可用作辅助剂以增强杀真菌剂和/或除草剂制剂的生物学效力。这些物质必须均匀分散在水性喷雾剂中，从而能均匀分布在田间所处理的表面上。因此，常将它们配制成可乳化浓缩物或最终配制成浓缩的粗乳剂(macroemulsion)并在应用前不久用水稀释。
对于矿物油，经典和传统制剂包含壬基酚乙氧基化物作为乳化剂。
脂肪醇乙氧基化物也可用作这些体系的乳化剂，如US 4,966,728(巴斯夫公司(BASF))所述。
目前对于用植物油替换矿物油的需求很高，因为前者的植物毒性更低并且具有更好的生态毒理学分布和环境影响。
酯交换的甘油三酯(transesterified triglycerides)和植物油是人们熟知的辅助剂，通常以乳化形式(通常自可乳化浓缩物获得)用于水性喷雾剂中。
许多基于油酸甲酯的罐内混合辅助剂描述为可乳化的液体形式，它们在用水稀释后形成动力学稳定的水包油粗乳剂。
植物油和/或甲基化植物油(酯交换的甘油三酯)比矿物油需要更复杂的乳化剂系统，特别是必须制备液体水包油粗乳剂之时。
用水稀释后能形成动力学稳定的水包油粗乳剂的低粘性可乳化液体表现出的主要缺点是由于常发生奶油状或油状分离，因此需要在应用前将产品良好均匀化。
因此，非常需要获得基于植物油和/或甲基化植物油的流体微乳剂形式的辅助剂。
药学应用辅助剂的文献中(例如，US 6,451,325和US 6,299,884)描述了亚微米液滴或微乳剂体系。
专利文献中还描述了农业化学应用的微乳剂。
US 6,589,913描述了显示微乳剂结构的农业化学草甘膦制剂。
US 5,905,072描述了作为全身性杀真菌剂的辅助剂的微乳剂，其含有脂肪酸甲酯及非离子和阴离子表面活性剂的特定混合物。
例如，US 6,255,253描述了在含有油相和农业化学品的微乳剂中应用烷基(寡聚)糖苷。
已知微乳剂中存在各种表面活性剂不仅影响组合物的稳定性，还可能增强农业化学制剂的生物学活性。
当通过常规水力喷雾将杀虫剂的稀释水性组合物应用于叶片时，稀释水性组合物中存在表面活性剂可改变喷雾液滴的尺寸分布，通常是增加小液滴形式喷雾体积的百分比并减少大液滴形式喷雾体积的百分比。
由于较小液滴具有的动量小于较大液滴，这些较小液滴比较不易从叶片表面弹开，从而更可能保留在该表面上。
还可通过喷雾液滴中的表面活性剂分子与叶片表面之间的黏附作用而促进喷雾保留性，对于大多数植物，所述叶片表面是蜡状和疏水性的。
这种黏附作用不仅减少喷雾剂液滴从叶片表面弹开还减少喷雾剂液滴从叶片表面流走。
表面活性剂还可能增加喷雾剂液滴与叶片表面之间的接触面积，在许多情况中能增强系统杀虫剂从液滴进入并穿过叶片角质层而到达叶片组织内部的渗透性。
系统杀虫剂化合物的分子必须穿过几道屏障。
在这些屏障中，据信最重要的是杀虫剂所应用的叶片表面的亲脂性角质层。
因此，在理论上优选将杀虫剂化合物置于两性介质内以维持亲脂性角质层和杀虫剂之间更好的相容性，从而促进杀虫剂渗透并进入角质层。
利用表面活性剂不难构建两性载体。
通过这些和可能的其它作用，早已知道包括表面活性剂在内的两性材料能增加杀虫剂的生物学作用并可用作辅助剂。
发明内容
现已发现当与水和特定用量及种类的表面活性剂共同配制时，可将从植物油酯交换获得的脂肪酸酯与植物油配制成生物学活性增强的微乳剂形式，例如稳定的透明清澈液体。
因此，本发明涉及稳定微乳剂形式的辅助剂，其包含：a)表面活性剂的混合物，其含有i)一种或多种烷基聚糖苷(alkylpolyglycoside)的阴离子衍生物；ii)一种或多种烷基聚糖苷；iii)一种或多种脂肪醇的阴离子衍生物；b)一种或多种衍生自植物油酯交换反应的脂肪酸甲基酯、一种或多种植物油、或它们的混合物；c)一种或多种非离子型表面活性剂；d)水。
本发明的辅助剂优选包含：a)5-20重量％的表面活性剂混合物，该混合物含有30重量％-60重量％的烷基聚糖苷的阴离子衍生物、30重量％-60重量％的烷基聚糖苷和5重量％-20重量％的脂肪醇的阴离子衍生物，它们配平为100；b)20-40重量％的衍生自植物油酯交换反应的脂肪酸甲基酯或20-40重量％的植物油；c)25-35重量％的非离子型表面活性剂；d)10-40重量％的水。
优选的非离子型表面活性剂是具有6-20个碳原子的线性或支链脂肪醇的乙氧基化和/或丙氧基化衍生物。
按照本发明的优选实施方式，本发明辅助剂包含：a)5-20重量％的表面活性剂混合物，该混合物含有30重量％-60重量％的烷基聚糖苷的阴离子衍生物、30重量％-60重量％的烷基聚糖苷和5重量％-20重量％的脂肪醇的阴离子衍生物，它们配平为100；b)20-40重量％的衍生自植物油酯交换反应的脂肪酸甲基酯或20-40重量％的植物油；c)25-35重量％的具有6-20个碳原子的线性或支链脂肪醇的乙氧基化和/或丙氧基化衍生物；d)10-40重量％的水。
可用作组分a)的表面活性剂的混合物描述于EP 1,179,979。
表面活性剂混合物中的烷基聚糖苷是式(I)R-O-(G)x所示的脂族烷基聚糖苷，式中：R是具有6-20个碳原子、线性或支链的饱和或不饱和脂族烷基；O是氧原子；G是通过醚O-糖苷键与R-O相连的还原糖的残基；x是1-10的数值，代表了G的平均寡聚聚合度。
R优选具有8-16个碳原子的烷基，G优选还原糖的残基，x优选1-2的数值。
本发明的优选烷基聚糖苷是式(I)所示化合物，式中G是葡萄糖的残基。
式(I)所示化合物及其制备方法是已知的，例如美国专利号3,219,656、3,547,828和3,839,318所述。
以上报道的式(I)所示优选化合物可商品化购得的产品，并且具有高生物可降解性。
表面活性剂混合物中的烷基聚糖苷的阴离子衍生物是式(II)[R′-O-(G)x]n-(D)y所示的化合物，式中：R′是具有6-20个碳原子，优选8-16个碳原子，饱和或不饱和，线性或支链的脂族烷基；G是通过醚O-糖苷键与R′-O相连的还原糖，优选葡萄糖的残基；O是氧原子；D是与残基G的氧原子相连的酰基残基，其衍生自包含具有2-8个碳原子的脂族链、线性或支链、饱和或不饱和、未取代或用一个或多个羟基取代的二元羧酸或多聚羧酸，其中至少一个羧基成盐或为酸形式；n是1和m-1之间的数值，其中m是衍生D的酸的羧基数；x与上述式(I)所示化合物具有相同的意义；y是1-10的数值，代表了(G)x的平均酯化程度。
本发明烷基聚糖苷的优选阴离子衍生物是式(II)所示化合物，式中R′是具有8-16个碳原子的烷基，D是选自下组羧酸的酰基残基：柠檬酸、磺基琥珀酸、酒石酸、马来酸和苹果酸。
上述式(II)所示烷基聚糖苷的阴离子衍生物是已知的，可根据，例如EP 258814或EP 510 564所述制备。
表面活性剂混合物的脂肪醇的阴离子衍生物如式(III)R″-O-D′所示，它们可通过用式R″-OH所示脂肪醇与羧酸酯化来制备，式中：R″是具有6-20个碳原子，优选8-16个碳原子的，饱和或不饱和，线性或支链的脂族烷基；O是氧原子；D′是具有2-8个碳原子的脂族链、饱和或不饱和、线性或支链、未取代或用一个或多个羟基取代的二元羧酸或多聚羧酸的酰基残基，其中至少一个羧基成盐或为酸形式。
本发明的脂肪醇的优选阴离子衍生物是式(III)所示化合物，式中D′是选自下组羧酸的酰基残基：柠檬酸、磺基琥珀酸、酒石酸、马来酸和苹果酸。
式(III)所示脂肪醇的阴离子衍生物的制备方法的例子报道于：柠檬酸酯表面活性剂(Citric Ester Surfactants)-P.J.Borchert等，-世界表面活性剂大会会议录(Proceeding of the World Surfactants Congress)-慕尼黑1984，第2卷，第147页。
实施本发明特别相关的是烷基聚糖苷的阴离子衍生物(II)和脂肪醇的阴离子衍生物(III)，式中D和D’是柠檬酸的酰基残基，其中至少一个羧基成盐，优选为钠盐形式。
在用于实施本发明的表面活性剂混合物中，式(I)所示化合物的R基团，式(II)所示化合物的R’基团和式(III)所示脂肪醇的R”基团可以彼此相同或不同。
类似地，在用于实施本发明的表面活性剂混合物中，式(II)所示化合物的D基团和式(III)所示化合物的D’基团可以彼此相同或不同。
本发明尤其优选其中R＝R′＝R″，同时D＝D′的表面活性剂混合物。
在可用作本发明微乳剂的组分b)的衍生自植物油酯交换反应的脂肪酸甲基酯中，特别优选油酸甲酯。
适用作组分b)的植物油的例子是玉米油、大豆油、菜籽油、葵花子油和它们的混合物。
具有6-20个碳原子并总共含有平均4-20个环氧乙烷和/或环氧丙烷单位的线性或支链脂肪醇的乙氧基化和/或丙氧基化衍生物优选作为组分c)；乙氧基化异癸基醇尤其优选作为组分c)。
本发明的微乳剂优选含有0-15重量％的防冻剂；合适的防冻剂是甘油和二元醇，例如单丙二醇(monopropylene glycol)、乙二醇、双丙二醇(dipropylene glycol)。
现已制备了人们熟知的单一辅助剂的许多混合物(主要是表面活性剂和酯交换的植物油)来研究它们的效力。
应该知道虽然用水稀释后本发明的微乳剂变成粗乳剂(水包油)，但该现象可逆：当水蒸发时，例如随沉积的液滴喷雾到田间时水发生蒸发，微乳剂再次形成，因而给叶片提供促进杀虫剂渗透的非常有效的辅助剂体系。
本发明的微乳剂增强许多叶片除草剂和系统杀真菌剂的活性。
当处理植物时，可将合适量的杀真菌剂或者含有所述杀真菌剂的商品化制剂加入辅助剂。这些商品化制剂通常是可乳化的液体、可润湿的粉末、浓缩的混悬液、水乳剂或微乳剂。
本发明辅助剂不难以0.05-0.5重量％，优选0.1-0.3重量％用量的加入除草剂或杀真菌制剂。
所用制剂的例子是含有以下组分的制剂：三唑(triazolic)、四康唑(tetraconazole)、三唑酮、三唑醇、丙环唑(propiconazole)、苄氯三唑醇(diclobutrazol)、双苯三唑醇(biternatol)、戊菌唑(penconazole)、粉唑醇(flutriafol)、六康唑(hexaconazole)、腈菌唑(myclobutanyl)、氟硅唑(flusilazole)、环唑醇(cyproconazole)、烯唑醇(diniconazole)、苯醚甲环唑(difenocaonazole)、氟环唑(epoxiconazole)；咪唑(imidazolic)；咪鲜胺(prochloraz)、伊米萨利；吗啉(morpholinic)；芬普福(fenpropimorph)；二甲十三烷吗啉；二羧基酰亚胺(dicarboxyimidic)；异菌脲(iprodione)、乙菌利(chlozolinate)、乙烯菌核利(vinclozolin)；哌啶(piperidinic)；苯锈啶(fenpropidin)；酰基丙胺(acylalanicinic)；甲霜灵(metalaxyl)、苯霜灵(benalaxyl)；草甘磷；草铵膦(Glufosinate)；MCPA；MCPP；2，4-滴丙酸(Diclorprop)；二氯甲氧苯酸(Dicamba)；苯达松；碘苯腈(loxynil)；溴草腈；甜菜宁(Phenmedipham)；甜菜安(Desmedipham)；乙呋草黄(Ethofumesate)；敌稗；氯磺隆(Chlorsulfuron)；甲磺隆(Methsulfuron)；嘧苯胺磺隆(Orthosulfamuron)；砜嘧磺隆(Rimsulfuron)；烟嘧磺隆(Nicosulfuron)。
活性系统杀真菌组分的优选来源主要由含有这些组分并以生产者推荐的最低剂量使用的商品化制剂构成。按照本发明一具体实施方式，还可制备不难稀释的浓缩杀真菌组合物，其含有一种或多种系统杀真菌剂和本发明辅助剂。
有这些制剂可用使得活性组分和辅助剂的剂量可以正确使用，因而能降低无经验操作者处理时带来的危险。
实施例中使用以下化合物：
乙氧基化脂肪醇：
CoA＝5摩尔乙氧基化十六烷基油醇
ISD＝90重量％的在水中配制的7摩尔乙氧基化异癸基醇
表面活性剂混合物(重量％)：
A＝含以下组分的30％水性溶液：47％C10-16烷基聚糖苷(n＝1.2)；45％C10-16烷基聚糖苷(n＝1.2)柠檬酸酯钠盐；8％C10-16脂肪醇柠檬酸酯钠盐。
B＝含以下组分的45％水性溶液：42％C10-16烷基聚糖苷(n＝1.2)；45％C10-16烷基聚糖苷(n＝1.2)磺基琥珀酸酯钠盐；6％C10-16脂肪醇磺基琥珀酸酯钠盐。
植物油的甲基酯：
MeO＝油酸甲酯
防冻剂：
MPG＝单丙二醇
实施例1-8
机械中速搅拌表1所列成分(数值以重量计)，通过匀化制备本发明微乳剂。
表1
| 实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 实施例7 | 实施例8 | |
| MeO | 25.5 | 31.5 | 31.5 | 30 | 31.3 | 31.5 | 31.5 | 31.5 |
| CoA | 8 | 10 | 30.0 | 30 | 31.3 | - | - | - |
| ISD | 31.5 | 31.5 | - | - | - | 31.5 | 31.2 | 31.2 |
| A | 29 | 30.5 | 33.5 | 29 | 28.1 | 31 | 28.1 | - |
| B | - | - | - | - | - | - | - | 28.1 |
| 水 | 2.5 | 4 | - | - | - | - | 3.1 | 3.1 |
| MPG | 10 | 9 | 6.5 | 10 | 9.4 | 6.5 | 6.2 | 6.2 |
实施例1-8的乳剂非常清澈而透明，储存稳定性良好：即，它们不仅在室温下，而且在10℃和40℃储存4周亦是均匀透明的液体。稀释度高时(实际剂量率)，其形成水包油粗乳剂。当制备的罐内混合物混合有含杀虫活性成分的合适制剂时，发生相同的情况。实施例1-8的微乳剂是可倾倒的低粘度液体(粘度＜100mPa-s)。
25℃，测定实施例7微乳剂的粒径显示平均粒径为15-40nm(仪器：N4Plus，考特尔公司(Coulter))。
Claims (5)
1.微乳剂，其包含：a)5-20重量%的表面活性剂的混合物，该混合物含有i)30重量%-60重量%的一种或多种烷基聚糖苷的阴离子衍生物；ii)30重量%-60重量%的一种或多种烷基聚糖苷；iii)5重量%-20重量%的一种或多种脂肪醇的阴离子衍生物，它们配平为100；b)20-40重量%的一种或多种衍生自植物油的酯交换反应的脂肪酸甲基酯；c)25-35重量%的一种或多种非离子型表面活性剂，其选自具有6-20个碳原子并总共含有平均4-20个环氧乙烷单位的线性或支链脂肪醇的乙氧基化衍生物；d)10-40重量%的水；
其中ii)烷基聚糖苷是式(I)R-O-(G)x所示的脂族烷基聚糖苷，式中：R是具有8-16个碳原子的烷基；O是氧原子；G是通过醚O-糖苷键与R-O相连的还原糖的残基；x是1-2的数值，代表了G的平均寡聚程度；
i)烷基聚糖苷的阴离子衍生物是式(II)[R′-O-(G)x]n-(D)y所示的化合物，式中：R′是具有8-16个碳原子的烷基；O是氧原子；G是通过醚O-糖苷键与R′-O相连的还原糖的残基；D是与残基G的氧原子相连的酰基残基，其是选自下组羧酸的酰基残基：柠檬酸、磺基琥珀酸、酒石酸、马来酸和苹果酸；n是1和m-1之间的数值，其中m是衍生D的酸的羧基数；x与上述式(I)所示化合物中具有相同的意义；y是1-10的数值，代表了(G)x的平均酯化程度；
iii)脂肪醇的阴离子衍生物如式(III)R"-O-D′所示，它们可通过用式R"-OH所示脂肪醇与羧酸酯化来制备，式中：R"是具有8-16个碳原子的烷基；O是氧原子；D′是选自下组羧酸的酰基残基：柠檬酸、磺基琥珀酸、酒石酸、马来酸和苹果酸；
其中式(I)所示化合物的R基团，式(II)所示化合物的R’基团和式(III)所示化合物的R”基团相同。
2.如权利要求1所述的微乳剂，其特征在于，在式(I)和(II)中，G是葡萄糖的残基。
3.如权利要求2所述的微乳剂，其特征在于，组分b)是油酸甲酯。
4.如权利要求3所述的微乳剂，其特征在于，在式(II)和(III)中，D和D’是柠檬酸的酰基残基，其中至少一个羧基成盐。
5.如权利要求4所述的微乳剂，其特征在于，组分c)是乙氧基化异癸基醇。
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| US9416065B2 (en) * | 2007-02-12 | 2016-08-16 | Archer Daniels Midland Company | Adjuvants and methods of using them |
| US8536095B2 (en) | 2008-07-03 | 2013-09-17 | Monsanto Technology Llc | Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants |
| EP2468092A4 (en) * | 2009-08-21 | 2013-08-07 | Earth Chemical Co | METHOD FOR ADMINISTERING A MEDICINE INTO A PLANT |
| US20110176872A1 (en) * | 2010-01-15 | 2011-07-21 | Lamberti Usa, Inc. | Process for wetting a water repellent soil |
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| WO2012057610A2 (en) | 2010-10-29 | 2012-05-03 | Emery Oleochemicals (M) Sdn. Bhd | A potentiator for soluble liquid herbicide |
| JP2014500794A (ja) | 2010-11-15 | 2014-01-16 | アーチャー−ダニエルズ−ミッドランド カンパニー | 組成物及び汚染物質の変換におけるその使用 |
| WO2013054197A1 (en) | 2011-10-13 | 2013-04-18 | Amril Ag | A potentiator for soluble liquid herbicide |
| CN111345290A (zh) * | 2012-03-05 | 2020-06-30 | 阿彻丹尼尔斯米德兰德公司 | 微乳液及其作为输送系统的用途 |
| CN104872114A (zh) * | 2014-06-13 | 2015-09-02 | 中国日用化学工业研究院 | 一种环境友好型杀虫微乳剂及其制备工艺 |
| WO2016075052A1 (en) | 2014-11-12 | 2016-05-19 | Lamberti Spa | Method of increasing lubricity of wellbore fluids |
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| EP0729700A2 (en) * | 1995-02-23 | 1996-09-04 | ISAGRO S.p.A. | Adjuvants for systemic fungicides, fungicidal compositions which contain them and their use |
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| WO2008019891A2 (en) | 2008-02-21 |
| CA2687617C (en) | 2014-02-18 |
| AU2007286439B2 (en) | 2013-01-17 |
| RU2009139954A (ru) | 2011-06-27 |
| US20100173782A1 (en) | 2010-07-08 |
| ES2525688T3 (es) | 2014-12-29 |
| EP2157854B1 (en) | 2014-09-10 |
| CN101702873A (zh) | 2010-05-05 |
| PL2157854T3 (pl) | 2015-03-31 |
| US8282950B2 (en) | 2012-10-09 |
| NZ580896A (en) | 2012-02-24 |
| CA2687617A1 (en) | 2008-02-21 |
| DK2157854T3 (en) | 2015-01-05 |
| AU2007286439A1 (en) | 2008-02-21 |
| BRPI0721665A2 (pt) | 2014-02-25 |
| ZA200907326B (en) | 2010-06-30 |
| ITVA20070047A1 (it) | 2008-11-25 |
| EP2157854A2 (en) | 2010-03-03 |
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