CN106455555A - 包含农药和羟烷基聚氧化烯二醇醚的组合物 - Google Patents
包含农药和羟烷基聚氧化烯二醇醚的组合物 Download PDFInfo
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- CN106455555A CN106455555A CN201580022630.1A CN201580022630A CN106455555A CN 106455555 A CN106455555 A CN 106455555A CN 201580022630 A CN201580022630 A CN 201580022630A CN 106455555 A CN106455555 A CN 106455555A
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- ethylidene
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Classifications
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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
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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Abstract
本发明涉及一种组合物，其包含农药和式(I)的羟烷基聚氧化烯二醇醚。本发明进一步涉及羟烷基聚氧化烯二醇醚作为含农药的喷雾混合物中的助剂的用途。本发明进一步涉及一种控制植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法，其中使所述组合物作用于相应害虫、其栖息地或待保护以防相应害虫的植物上、作用于土壤上和/或作用于不希望的植物和/或作物和/或其生长地上。此外，本发明涉及包含所述组合物的种子。本发明包括优选特征与其他优选特征的组合。
Description
本发明涉及一种包含农药和式(I)的羟烷基聚氧化烯二醇醚的组合物。本发明进一步涉及羟烷基聚氧化烯二醇醚作为含农药的喷雾混合物中的助剂的用途。本发明进一步涉及一种控制植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法，其中使所述组合物作用于相应害虫、其栖息地或待保护以防相应害虫的植物上、作用于土壤上和/或作用于不希望的植物和/或作物和/或其生长地上。此外，本发明涉及包含所述组合物的种子。
本发明包括优选特征与其他优选特征的组合。
公知的农业实践是在配制剂中添加特定助剂以提高配制剂的活性。有利的是，这能减少配制剂中的活性成分量，同时保持相同的活性，由此能使成本降至最低，且合适的话，能在现有立法框架内操作。在各种情况下，这还能拓宽活性成分的作用谱，因为在无添加物下仅可用特定活性成分以不令人满意的程度防治的植物现在由于添加特定辅助剂而能进行该处理。此外，在每种情况下可通过合适的配制剂提高在不利环境条件下的性能。当然，还可避免各种活性成分在一种配制剂中的不相容性。该类辅助剂有时也称为助剂。它们通常呈表面活性或盐状化合物的形式。就活性成分在叶片中的吸收而言，表面活性物质可起改性剂和助剂的作用。通常认为合适的表面活性物质能通过提供更好的润湿而提高流体在叶片上的有效接触面积。此外，某些表面活性物质起增塑剂的作用，即能将表皮蜡质层从晶态转变成无定形态，这有助于活性成分的吸附。此外，一些表面活性物质还能改善活性成分在配制剂中的溶解性，由此避免或至少延迟晶体的形成。最后，在某些情况下，它们还可通过保留水分而影响活性成分的吸收。
通常用作助剂的合成表面活性物质尤其利用具有8-13的HLB值的聚氧化乙烯与醇、烷基酚或烷基胺的缩合物。就此而言，文献WO00/42847提及例如使用特定直链醇烷氧基化物来提高农业化学生物杀伤剂配制剂的活性。
特别地，正是醇结构部分的结构以及在某些情况下还有烷氧基化物结构部分及其端基的结构影响了该表面活性剂的性能，从而导致在这些应用中显示出有用性的各种技术效果。这些包括润湿、铺展、渗透、粘合、成膜、改进相容性、漂移控制和消泡。
WO03/090531描述了使用特定支化醇的烷氧基化物作为农业化学领域的助剂。WO2005/015998具体提出将类似的醇烷氧基化物用作杀真菌苯甲酰胺肟衍生物的助剂。WO00/35278涉及基于2-乙基己醇的PO/EO嵌段共聚物的农业化学配制剂。WO2005/084435描述了油基悬浮液浓缩物，其包含一种两个端基被封端的醇嵌段烷氧基化物作为渗透剂。WO08/132150和WO09/130281还描述了具有助剂活性的特定醇烷氧基化物。WO03/022048尤其描述了作为助剂的C1-C7烷基封端的油基醇乙氧基化物，其中该化合物的制备由于使用烷基氯而是相当危险的。
本发明基于如下目的：提供可用于农业化学领域的其他助剂。
所述目的通过一种组合物实现，其包含农药和通式(I)的羟烷基聚氧化烯二醇醚：
其中：
R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基；
R2为亚乙基、亚丙基、亚丁基或其混合物；
R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基；且
n具有1-100的值。
R1优选为具有8-14个碳原子的饱和或不饱和、直链或支化烷基，尤其优选具有8-14个碳原子的饱和直链烷基。在尤其优选的实施方案中，R1为具有8-12个碳原子的饱和直链烷基。在另一尤其优选的实施方案中，R1为具有8或10个碳原子的饱和直链烷基。
R2优选为亚乙基、亚丙基或亚丁基或其混合物。就此而言，R2可例如包含这些基团的混合物。该类混合物可以以任何所需的顺序彼此连接，例如无规或嵌段连接(例如一个亚乙基嵌段和一个亚丙基嵌段)。在优选实施方案中，R2为亚乙基，或亚乙基和亚丙基的混合物。在另一优选实施方案中，R2为亚乙基。
如果R2包含亚丁基，则后者可以以亚正丁基、亚异丁基或2,3-亚丁基的形式存在，其中优选亚正丁基或亚异丁基，最优选亚正丁基。
R3优选为具有8-12个碳原子的饱和或不饱和支化烷基，尤其优选R3为具有8-12个碳原子的饱和支化烷基。在另一形式中，R3优选为具有8-16个碳原子的饱和或不饱和、直链或支化烷基，尤其优选R3为具有8-14个碳原子的饱和直链或支化烷基。在另一尤其优选的实施方案中，R3为异癸基、2-丙基庚基或2-乙基己基。在另一优选实施方案中，R3为具有8-10个碳原子的饱和直链烷基。
优选地，n具有3-50，尤其优选5-40的值。n的值通常为平均值，因为其大多取决于环氧乙烷衍生物的烷氧基化。因此，n不仅可为整数，而且可为整数之间的所有值。
在另一形式中，所述羟烷基聚氧化烯二醇醚具有通式(II)：
R1-CH(OH)-CH2-[O-R2a]x-[O-R2b]y-[O-R2c]Z-O-R3 (II)
其中：
R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基；
R2a、R2b和R2c独立地为亚乙基、亚丙基或亚丁基；
R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基；
x、y和z独立地为0-100的值；且
x、y和z加和为1-100的值。
R2a、R2b和R2c独立地为亚乙基、亚丙基或亚丁基。在优选实施方案中，R2a、R2b和R2c独立地为亚乙基或亚丙基。
优选地，x、y和z独立地为0-50，尤其优选0-40的值。x、y和z的值通常为平均值，因为其大多取决于环氧乙烷衍生物的烷氧基化。因此，x、y和z不仅可为整数，而且可为整数之间的所有值。
优选地，x、y和z加和为3-50，尤其优选5-40的值。x、y和z之和的值通常为平均值，因为其大多取决于环氧乙烷衍生物的烷氧基化。因此，该值不仅可为整数，而且可为整数之间的所有值。
在一种形式中，R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R2a为亚乙基，x为1-50，R2b为亚丙基，y为1-50，R2c为亚乙基或亚丙基，z为0-50，且x、y和z加和为2-100的值。
在优选形式中，R1为具有6-16个碳原子的饱和或不饱和、直链或支化烷基，R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R2a为亚乙基，x为1-25，R2b为亚丙基，y为1-25，R2c为亚乙基或亚丙基，z为0-20，且x、y和z加和为2-50的值。
在另一形式中，R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R2a为亚丙基，x为1-50，R2b为亚乙基，y为1-50，R2c为亚乙基或亚丙基，z为0-50(其中z优选为0)，且x、y和z加和为2-100的值。
在另一优选形式中，R1为具有6-16个碳原子的饱和或不饱和、直链或支化烷基，R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R2a为亚丙基，x为1-25，R2b为亚乙基，y为1-25，R2c为亚乙基或亚丙基，z为0-20(其中z优选为0)，且x、y和z加和为2-50的值。
在另一形式中，R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R2a为亚乙基，x为1-50，且y和z为0。
在另一优选形式中，R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基，R3为具有6-16个碳原子的饱和或不饱和、直链或支化烷基，R2a为亚乙基，x为1-20，且y和z为0。
在大多数情况下，本发明的组合物包含0.1-50重量％，优选1-25重量％，特别是3-15重量％上文所定义的羟烷基聚氧化烯二醇醚。
术语“农药”是指至少一种选自杀真菌剂、杀昆虫剂、杀线虫剂、除草剂、安全剂、杀软体动物剂、杀啮齿动物剂和/或生长调节剂的活性物质。优选的农药为杀真菌剂、杀昆虫剂、除草剂和生长调节剂。尤其优选的农药为杀真菌剂。也可使用两种或更多种上述类别的农药的混合物。本领域技术人员熟知该类农药，其可参见例如Pesticide Manual，第16版(2013)，The British Crop Protection Council，London。上文所公开的农药可与本发明的羟烷基聚氧化烯二醇醚组合。合适的杀昆虫剂为选自如下类别的杀昆虫剂：氨基甲酸酯类、有机磷酸酯类、有机氯杀昆虫剂、苯基吡唑类、拟除虫菊酯类、新烟碱类、斯皮诺素(spinosin)类、阿维菌素(avermectin)类、米尔贝霉素(milbemycin)类、保幼激素类似物、烷基卤、有机锡化合物、沙蚕毒素类似物、苯甲酰脲类、双酰肼类、METI杀螨剂；以及杀昆虫剂如氯化苦(chloropicrin)、拒嗪酮(pymetrozin)、氟啶虫酰胺(flonicamid)、四螨嗪(clofentezin)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、杀螨硫隆(diafenthiuron)、克螨特(propargite)、三氯杀螨砜(tetradifon)、氟唑虫清(chlorfenapyr)、二硝甲酚(DNOC)、噻嗪酮(buprofezine)、灭蝇胺(cyromazine)、虫螨脒(amitraz)、灭蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)、鱼藤酮(rotenone)或其衍生物。合适的杀真菌剂为如下类别的杀真菌剂：二硝基苯胺类、烯丙基胺类、苯胺基嘧啶类、抗生素、芳族烃类、苯磺酰胺类、苯并咪唑类、苯并异噻唑类、二苯甲酮类、苯并噻二唑类、苯并三嗪类、苄基氨基甲酸酯类、氨基甲酸酯类、羧酰胺类、羧酸二酰胺类、氯腈类、氰基乙酰胺肟类、氰基咪唑类、环丙烷羧酰胺类、二羧酰亚胺类、二氢二嗪类、二硝基苯基巴豆酸酯类、二硫代氨基甲酸酯类、二硫戊环类、乙基膦酸酯类、乙基氨基噻唑羧酰胺类、胍类、羟基-(2-氨基)嘧啶类、羟基苯胺类、咪唑类、咪唑啉酮类、无机物质、异苯并呋喃酮类、甲氧基丙烯酸酯类、甲氧基氨基甲酸酯类、吗啉类、N-苯基氨基甲酸酯类、唑烷二酮类、肟基乙酸酯类、肟基乙酰胺类、肽基嘧啶核苷类、苯基乙酰胺类、苯基酰胺类、苯基吡咯类、苯基脲类、膦酸酯类、硫代磷酸酯类、邻氨甲酰苯甲酸类、苯邻二甲酰亚胺类、哌嗪类、哌啶类、丙酰胺类、哒嗪酮类、吡啶类、吡啶基甲基苯甲酰胺类、嘧啶胺类、嘧啶类、嘧啶酮腙类、吡咯并喹啉酮类、喹唑啉酮类、喹啉类、醌类、磺酰胺类、氨磺酰基三唑类、噻唑羧酰胺类、硫代氨基甲酸酯类、苯硫脲酯类(thiophanate)、噻吩羧酰胺类、甲苯甲酰胺类、三苯基锡化合物、三嗪类、三唑类。合适的除草剂为如下类别的除草剂：乙酰胺类、酰胺类、芳氧基苯氧基丙酸酯类、苯甲酰胺类、苯并呋喃类、苯甲酸类、苯并噻二嗪酮类、联吡啶类、氨基甲酸酯类、氯乙酰胺类、氯羧酸类、环己烷二酮类、二硝基苯胺类、二硝基苯酚、二苯醚、甘氨酸类、咪唑啉酮类、异唑类、异唑烷二酮类、腈类、N-苯基苯邻二甲酰亚胺类、二唑类、唑烷二酮类、氧基乙酰胺类、苯氧基羧酸类、苯基氨基甲酸酯类、苯基吡唑类、苯基吡唑啉类、苯基哒嗪类、次膦酸类、氨基磷酸酯类、二硫代磷酸酯类、邻氨甲酰苯甲酸酯类、吡唑类、哒嗪酮类、吡啶类、吡啶羧酸类、吡啶羧酰胺类、嘧啶二酮类、嘧啶基(硫代)苯甲酸酯类、喹啉羧酸类、缩氨基脲类、磺酰氨基羰基三唑啉酮类、磺酰脲类、四唑啉酮类、噻二唑类、硫代氨基甲酸酯类、三嗪类、三嗪酮类、三唑类、三唑啉酮类、三唑羧酰胺类、三唑并嘧啶类、三酮类、尿嘧啶类、脲类。
所述农药优选具有在水中在20℃小于10g/l，更优选小于1g/l，甚至更优选小于0.5g/l，最优选小于0.1g/l的溶解度。
本发明组合物的优选农药包括至少一种选自羧酰胺类、唑类、嗜球果伞素类、苯基酰胺类、苯基吡咯类、吗啉类、螺缩酮胺类和二硫代氨基甲酸酯类的杀真菌剂。特别优选选自吡唑-4-羧酰胺类、吡啶基-乙基苯甲酰胺类、苯基苯甲酰胺类、三唑类和嗜球果伞素类的杀真菌剂。在更优选的实施方案中，所述杀真菌剂选自啶酰菌胺(boscalid)、氧唑菌(epoxiconazole)、氟唑菌酰胺(fluxapyroxad)和醚菌胺(dimoxystrobin)。
尤其优选地，本发明组合物的农药包含至少一种杀真菌剂和另一种农药(例如至少一种除草剂、杀昆虫剂和/或安全剂，优选除草剂)。
此外，本发明的组合物可转化成农业化学组合物的常规类型，例如溶液、乳液、悬浮液、粉剂、粉末、糊、颗粒、模压品、胶囊及其混合物。组合物类型的实例为悬浮液(例如SC、OD、FS)，可乳化浓缩物(例如EC)，乳液(例如EW、EO、ES、ME)，胶囊(例如CS、ZC)，糊，锭剂，可湿性粉末或粉剂(例如WP、SP、WS、DP、DS)，模压品(例如BR、TB、DT)，颗粒(例如WG、SG、GR、FG、GG、MG)，杀昆虫制品(例如LN)，以及用于处理植物繁殖材料如种子的凝胶配制剂(例如GF)。这些和其他组合物类型定义于“Catalogue of pesticide formulation types andinternational coding system”，Technical Monograph，第2期，第6版，2008年5月，CropLife International中。
所述组合物以已知方式制备，例如如Mollet和Grubemann，Formulationtechnology，Wiley VCH，Weinheim，2001；或Knowles，New developments in cropprotection product formulation，Agrow Reports DS243，T&F Informa，London，2005所述。
合适辅助剂的实例为溶剂、液体载体、固体载体或填料、表面活性剂、分散剂、乳化剂、润湿剂、助剂、加溶剂、渗透提高剂、保护性胶体、粘合剂、增稠剂、保湿剂、趋避剂、引诱剂、进食刺激剂、增容剂、杀菌剂、防冻剂、消泡剂、着色剂、增粘剂和粘结剂。
合适的溶剂和液体载体为水和有机溶剂，例如中至高沸点的矿物油馏分如煤油和柴油；植物或动物来源的油；脂族、环状和芳族烃类，例如甲苯、石蜡、四氢化萘、烷基化萘；醇，例如乙醇、丙醇、丁醇、苄醇、环己醇；二醇；DMSO；酮，例如环己酮；酯，例如乳酸酯、碳酸酯、脂肪酸酯、γ-丁内酯；脂肪酸；膦酸酯；胺；酰胺，例如N-甲基吡咯烷酮、脂肪酸二甲基酰胺、二甲基乳酰胺；及其混合物。
合适的固体载体或填料为矿土如硅酸盐、硅胶、滑石、高岭土、石灰石、石灰、白垩、粘土、白云石、硅藻土、膨润土、硫酸钙、硫酸镁、氧化镁；多糖粉末如纤维素、淀粉；肥料如硫酸铵、磷酸铵、硝酸铵、脲类；植物来源的产品如谷粉、树皮粉、木粉、坚果壳粉及其混合物。
合适的表面活性剂为表面活性化合物，例如阴离子、阳离子、非离子和两性表面活性剂、嵌段聚合物、聚电解质及其混合物。该类表面活性剂可用作乳化剂、分散剂、加溶剂、润湿剂、渗透提高剂、保护性胶体或助剂。表面活性剂的实例列于McCutcheon’s，第1卷：Emulsifiers&Detergents，McCutcheon’s Directories，Glen Rock，USA，2008(国际版或北美版)中。
合适的阴离子表面活性剂为磺酸、硫酸、磷酸、羧酸及其混合物的碱金属、碱土金属或铵盐。磺酸盐的实例为烷基芳基磺酸盐、二苯基磺酸盐、α-烯烃磺酸盐、木素磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基酚的磺酸盐、烷氧基化芳基酚的磺酸盐、缩合萘的磺酸盐、十二烷基-和十三烷基苯磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例为脂肪酸和油的硫酸酯盐、乙氧基化烷基酚的硫酸酯盐、醇的硫酸酯盐、乙氧基化醇的硫酸酯盐、脂肪酸酯的硫酸盐。磷酸盐的实例为磷酸酯盐。羧酸盐的实例为烷基羧酸盐和羧化醇或烷基酚乙氧基化物。
合适的非离子表面活性剂为烷氧基化物，N-取代的脂肪酸酰胺，胺氧化物，酯，糖基表面活性剂，聚合物表面活性剂及其混合物。烷氧基化物的实例为诸如已经被1-50当量烷氧基化的醇、烷基酚、胺、酰胺、芳基酚、脂肪酸或脂肪酸酯的化合物。可将氧化乙烯和/或氧化丙烯用于烷氧基化，优选氧化乙烯。N-取代的脂肪酸酰胺的实例是脂肪酸葡糖酰胺或脂肪酸链烷醇酰胺。酯的实例为脂肪酸酯，甘油酯或甘油单酯。糖基表面活性剂的实例为脱水山梨醇、乙氧基化脱水山梨醇、蔗糖和葡萄糖酯或烷基多葡糖苷。聚合物表面活性剂的实例为乙烯基吡咯烷酮、乙烯醇或乙酸乙烯酯的均聚物或共聚物。
合适的阳离子表面活性剂为季型表面活性剂，例如具有1或2个疏水性基团的季铵化合物，或长链伯胺的盐。合适的两性表面活性剂为烷基甜菜碱和咪唑啉类。合适的嵌段聚合物为包含聚氧化乙烯和聚氧化丙烯嵌段的A-B或A-B-A型嵌段聚合物，或包含链烷醇、聚氧化乙烯和聚氧化丙烯的A-B-C型嵌段聚合物。合适的聚电解质为聚酸或聚碱。聚酸的实例为聚丙烯酸的碱金属盐或聚酸梳状聚合物。聚碱的实例是聚乙烯基胺或聚乙烯胺。
合适的助剂是本身具有可忽略的农药活性或者本身甚至没有农药活性且改善该活性物，即农药对目标物的生物学性能的化合物。实例为表面活性剂，矿物油或植物油以及其他辅助剂。其他实例由Knowles，Adjuvants and Additives，Agrow Reports DS256，T&FInforma UK，2006，第5章列出。
合适的增稠剂为多糖(例如黄原胶、羧甲基纤维素)、无机粘土(有机改性的或未改性的)、聚羧酸盐和硅酸盐。
合适的杀菌剂为拌棉醇(bronopol)和异噻唑啉酮衍生物如烷基异噻唑啉酮类和苯并异噻唑啉酮类。
合适的防冻剂为乙二醇、丙二醇、尿素和甘油。
合适的消泡剂为聚硅氧烷、长链醇和脂肪酸的盐。
合适的着色剂(例如呈红色、蓝色或绿色)为低水溶性颜料和水溶性染料。实例为无机着色剂(例如氧化铁、氧化钛、六氰合铁酸铁)和有机着色剂(例如茜素着色剂、偶氮着色剂和酞菁着色剂)。
合适的增粘剂或粘结剂为聚乙烯基吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇、聚丙烯酸酯、生物或合成蜡，和纤维素醚。
组合物类型的实例及其制备为：
i)水溶性浓缩物(SL，LS)
将10-60重量％本发明农药和5-15重量％润湿剂(例如醇烷氧基化物)溶于至100重量％的水和/或水溶性溶剂(例如醇)中。活性物质在用水稀释时溶解。
ii)分散性浓缩物(DC)
将5-25重量％本发明农药和1-10重量％分散剂(例如聚乙烯基吡咯烷酮)溶于至100重量％的有机溶剂(例如环己酮)中。用水稀释得到分散体。
iii)可乳化浓缩物(EC)
将15-70重量％本发明农药和5-10重量％乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于至100重量％的水不溶性有机溶剂(例如芳烃)中。用水稀释得到乳液。
iv)乳液(EW，EO，ES)
将5-40重量％本发明农药和1-10重量％乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于20-40重量％水不溶性有机溶剂(例如芳烃)中。借助乳化机将该混合物引入至100重量％的水中并制成均质乳液。用水稀释得到乳液。
v)悬浮液(SC，OD，FS)
在搅拌的球磨机中，在加入2-10重量％分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)、0.1-2重量％增稠剂(例如黄原胶)和至100重量％水下，将20-60重量％本发明农药粉碎，得到精细的活性物质悬浮液。用水稀释得到活性物质的稳定悬浮液。对FS类型组合物，添加至多40重量％粘结剂(例如聚乙烯醇)。
vi)水分散性颗粒和水溶性颗粒(WG，SG)
在加入至100重量％分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)下，将50-80重量％本发明农药细碎研磨，借助工业装置(例如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到活性物质的稳定分散体或溶液。
vii)水分散性粉末和水溶性粉末(WP，SP，WS)
在加入1-5重量％分散剂(例如木素磺酸钠)、1-3重量％润湿剂(例如醇乙氧基化物)和至100重量％固体载体(例如硅胶)下，将50-80重量％本发明农药在转子-定子磨机中研磨。用水稀释得到活性物质的稳定分散体或溶液。
viii)凝胶(GW，GF)
在搅拌式球磨机中，在加入3-10重量％分散剂(例如木素磺酸钠)、1-5重量％增稠剂(例如羧甲基纤维素)和至100重量％水下研磨5-25重量％本发明农药，得到活性物质的精细悬浮液。用水稀释得到活性物质的稳定悬浮液。
ix)微乳液(ME)
将5-20重量％本发明农药添加至5-30重量％有机溶剂混合物(例如脂肪酸二甲基酰胺和环己酮)、10-25重量％表面活性剂混合物(例如醇乙氧基化物和芳基酚乙氧基化物)和至100％的水中。将该混合物搅拌1小时，自发产生热力学稳定的微乳液。
x)微胶囊(CS)
将包含5-50重量％本发明农药、0-40重量％水不溶性有机溶剂(例如芳烃)、2-15重量％丙烯酸系单体(例如甲基丙烯酸甲酯、甲基丙烯酸和二-或三丙烯酸酯)的油相分散至保护性胶体(例如聚乙烯醇)的水溶液中。由自由基引发剂引发的自由基聚合导致形成聚(甲基)丙烯酸酯微胶囊。或者，将包含5-50重量％本发明农药、0-40重量％水不溶性有机溶剂(例如芳烃)和异氰酸酯单体(例如4,4’-二苯甲烷二异氰酸酯)的油相分散至保护性胶体(例如聚乙烯醇)的水溶液中。添加聚胺(例如六亚甲基二胺)导致形成聚脲微胶囊。单体量为1-10重量％。该重量％相对于总CS组合物。
xi)可撒粉粉末(DP，DS)
将1-10重量％本发明农药细碎研磨并与至100重量％的固体载体，例如细碎高岭土充分混合。
xii)颗粒(GR，FG)
将0.5-30重量％本发明农药细碎研磨并结合至100重量％的固体载体(例如硅酸盐)。通过挤出、喷雾干燥或流化床实现造粒。
xiii)超低容量液体(UL)
将1-50重量％本发明农药溶于至100重量％有机溶剂如芳烃中。
组合物类型i)至xiii)可任选包含其他辅助剂，例如0.1-1重量％杀菌剂、5-15重量％防冻剂、0.1-1重量％消泡剂和0.1-1重量％着色剂。
所述农业化学组合物通常包含0.01-95重量％，优选0.1-90重量％，最优选0.5-75重量％的农药。活性物质以90-100％，优选95-100％的纯度使用(根据NMR谱)。
通常将水溶性浓缩物(LS)，悬浮乳液(SE)、可流动浓缩物(FS)、干处理用粉末(DS)、淤浆处理用水分性粉末(WS)、水溶性粉末(SS)、乳液(ES)、可乳化浓缩物(EC)和凝胶(GF)用于处理植物繁殖材料，特别是种子的目的。所述组合物在稀释2-10倍后得到在即用型制剂中为0.01-60重量％，优选0.1-40重量％的活性物质浓度。施用可在播种之前或期间进行。将农药及其组合物分别施用至植物繁殖材料，尤其是种子，或对其进行处理的方法包括繁殖材料的拌种、包衣、造粒、撒粉、浸泡和犁沟内施用方法。优选地，通过不诱发萌芽的方法，例如通过拌种、造粒、包衣和撒粉将农药或其组合物分别施用至植物繁殖材料上。
当用于植物保护中时，活性物质的施用量取决于所需的效果类型为0.001-2kg/ha，优选0.005-2kg/ha，更优选0.05-0.9kg/ha，特别是0.1-0.75kg/ha。
在植物繁殖材料如种子的处理(例如通过撒粉、包衣或浸泡种子)中，通常要求活性物质的量为0.1-1000g/100kg，优选1-1000g/100kg，更优选1-100g/100kg，最优选5-100g/100kg繁殖材料(优选种子)。
当用于保护材料或储存产品中时，活性物质的施用量取决于施用区域的类型和所需的效果。在材料保护中常用的施用量为0.001g至2kg，优选0.005g至1kg活性物质/立方米被处理材料。
可向活性物质或包含它们的组合物中加入各种类型的油、润湿剂、助剂、肥料或微量营养素和其他农药(例如除草剂、杀昆虫剂、杀真菌剂、生长调节剂、安全剂)以作为预混物，或者合适的话在紧临使用前加入(桶混剂)。这些试剂可以以1:100-100:1，优选1:10-10:1的重量比与本发明的组合物混合。
用户通常由预剂量装置、背包式喷雾器、喷雾桶、喷雾飞机或灌溉系统施用本发明的组合物。通常用水、缓冲剂和/或其他辅助剂将所述农业化学组合物配制至所需的施用浓度，由此获得即用喷雾液或本发明的农业化学组合物。每公顷农业利用区通常施用20-2000升，优选50-400升即用喷雾液。
本发明的组合物可包含0.1-40重量％，优选1-30重量％，特别是2-20重量％表面活性物质(如上文所公开)，其中不考虑本发明羟烷基聚氧化烯二醇醚的量。
此外，本发明涉及一种控制植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法，其中使本发明的组合物作用于相应害虫、其环境或待保护以防该相应害虫的作物上、作用于土壤上和/或作用于不希望的植物和/或作物和/或其环境上。
合适作物的实例为禾谷类，例如小麦、黑麦、大麦、小黑麦、燕麦或稻；甜菜，例如糖用甜菜或饲用甜菜；仁果、核果和浆果，例如苹果、梨、李、桃、杏仁、樱桃、草莓、悬钩子、黑莓或鹅莓；豆科植物，例如蚕豆、兵豆、豌豆、苜蓿或大豆；油料作物，例如油菜籽油菜、芥菜、橄榄、向日葵、椰子、可可豆、蓖麻豆、油棕、花生或大豆；葫芦科植物，例如南瓜、黄瓜或甜瓜；纤维作物，例如棉花、亚麻、大麻或黄麻；柑桔类水果，例如橙子、柠檬、葡萄柚或橘；蔬菜植物，例如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、西红柿、土豆、南瓜或或柿子椒；月桂科植物，例如鳄梨、肉桂或樟脑；能量作物和工业原料作物，例如玉米、大豆、小麦、油菜籽油菜、甘蔗或油棕；烟草；坚果；咖啡；茶；香蕉；葡萄(食用葡萄和酿酒用葡萄)；啤酒花；禾草，例如草坪；甜叶菊(Stevia rebaudania)；橡胶植物和森林植物，例如花卉、灌木、落叶树和针叶树；和植物繁殖材料，例如种子；以及这些植物的收获产品。
术语“作物”还包括已经通过育种、诱变或重组方法修饰的那些植物，包括上市销售或处于开发过程中的农业生物技术产品。基因修饰植物是其基因材料以在自然条件下无法通过杂交、突变或自然重组(即基因材料的重组)进行的方式修饰的植物。此时，通常将一个或多个基因整合到植物的基因材料中以改善植物的性能。该类重组修饰还包括蛋白质、寡肽或多肽的翻译后修饰，例如通过糖基化或连接聚合物，例如异戊二烯化、乙酰化或法呢基化基团或PEG基团。
可提及的实例为由于植物育种和重组措施而获得对某些类别除草剂的耐受性的植物，所述除草剂例如为羟基苯基丙酮酸双加氧酶(HPPD)抑制剂，乙酰乳酸合成酶(ALS)抑制剂如磺酰脲类(EP-A-0257993，US 5,013,659)或咪唑啉酮类(例如US 6,222,100、WO 01/82685、WO 00/026390、WO 97/41218、WO 98/002526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/014357、WO 03/13225、WO 03/14356、WO 04/16073)，烯醇丙酮酰莽草酸3-磷酸合成酶(EPSPS)抑制剂如草甘膦(glyphosate)(例如参见WO 92/00377)，谷氨酰胺合成酶(GS)抑制剂如草铵膦(glufosinate)(例如参见EP-A-0242236、EP-A-242 246)或oxynil除草剂(例如参见US 5,559,024)。例如，育种和诱变已得到油菜籽油菜(德国BASF SE)，其特征在于耐受咪唑啉酮类如咪草啶酸(imazamox)。已经借助重组方法产生耐受草甘膦或草铵膦的作物如大豆、棉花、玉米、甜菜和油菜籽油菜，且这些可以以商标名(耐受草甘膦，美国Monsanto)和Liberty(耐受草铵膦，德国Bayer CropScience)获得。
羟烷基聚氧化烯二醇醚的制备是公知的。其通常通过使脂肪醇与烷氧基化的支化烷基环氧乙烷在碱性催化剂存在下反应而制备。该制备方法本身是已知的，且还公开于EP0299360A2中。
此外，本发明涉及一种制备本发明组合物的方法，包括使所述农药和通式(I)的羟烷基聚氧化烯二醇醚接触，例如通过混合。接触可在5-95℃下进行。因此，可制备桶混剂或农业化学组合物。
本发明还涉及上文所公开的本发明羟烷基聚氧化烯二醇醚作为含农药的喷雾混合物中的助剂的用途。所述助剂优选为活性提高性助剂。与不存在所述助剂下的农药活性相比，它们提高或促进了农药的活性。
本发明还涉及一种改善一种或多种农药的活性的方法，包括将有效量的本发明羟烷基聚氧化烯二醇醚与一种或多种本公开内容中所述的农药混合的步骤。
本发明的优点是本发明的羟烷基聚氧化烯二醇醚能提高农药的活性；提高产量；提高农药在植物中的吸收；降低配制剂的表面张力。
下文实施例阐述了本发明，而不施加任何限制。
实施例
材料和方法：
化合物A：
化合物B：
化合物C：
实施例1—合成羟烷基聚氧化烯二醇醚
a)制备化合物C
将130.23g异辛醇和1.3g 30％于甲醇中的甲醇钠装入高压釜中。在80-100℃下，形成异辛醇的醇盐，并通过在50-100毫巴下真空蒸馏移除甲醇。然后通过供入氮气移除真空。此外，用氮气吹扫高压釜两次，然后将温度升至150-160℃，并在160-180℃的最高温度和5巴的最高压力下供入396g氧化乙烯。在氧化乙烯添加结束后，将反应混合物再在160-180℃下搅拌30分钟。然后，将产物冷却至80℃。
在反应的第二步中，在氮气和160-180℃的温度下经约2小时的时间添加额外量的催化剂，优选3.5g KOH和进料156g 1,2-氧化癸烯。在反应结束后，将产物冷却至80℃并中和。
b)制备化合物A和B
对化合物A和化合物B的制备可使用类似的程序，其中由不同的支化或直链脂肪醇、不同量的氧化乙烯和不同的1,2-环氧化烯烃出发。
实施例2—大田试验
在德国南部的Parabraunerde土壤上根据GEP分别在商业种植的暴露于海洋气候的冬小麦(Akteur品种)和冬油菜(Genie品种)上进行大田研究。标准试验设计为随机完全区组设计，重复4次。不实施人工侵染。杀真菌剂以其标称施用率(N)和当与助剂在桶中混合时，以半剂量(N/2)施用。助剂的剂量率为150ml/ha。功效通过产量以dt/ha测量。在偏差分析后，以5％的显著水平使用平均离散测试(Student-Newman-Keuls)。所有处理是完全选择性的。
冬小麦
使用AirMix 110-03喷嘴在1.9巴压力下施用200L/ha的喷雾体积。用地为2.5m×7m大。在生长阶段(BBCH)32和51时两次施用具有分散添加剂(基于萘磺酸甲醛缩合产物，钠盐)的氧唑菌SC 125。在试验期间，存在壳针孢属(Septoria)和褐锈病的自然侵染。在每次处理时，助剂的剂量率为150ml/ha。
油菜
使用AirMix 110-03喷嘴在2.1巴压力下施用250L/ha的喷雾体积。用地为3m×7m大。在Parabraunerde土壤上在油菜的生长阶段(BBCH)51时施用Gold SC(200g/l啶酰菌胺(boscalid)和200g/l醚菌胺(dimoxystrobin)，其具有基于羟基苯磺酸钠盐与甲醛、苯酚和脲的聚合物的分散添加剂)。在试验期间，存在核盘菌属(Sclerotinia sp.)的自然侵染。在每次处理时，助剂的剂量率为150ml/ha。
结果
对定量测量而言，测定每次处理的产量。
表1：冬小麦产量
| 相对产量(％) | |
| _a) | 100.0 |
| N/2(半剂量的氧唑菌) | 103.5 |
| N/2+化合物A | 108.7 |
| N/2+化合物B | 107.7 |
| N/2+化合物C | 109.4 |
a)对比试验，非本发明，不含助剂。
表2：油菜籽产量
| 相对产量(％) | |
| _a) | 100.0 |
| N/2(半剂量的氧唑菌) | 103.1 |
| N/2+化合物A | 107.1 |
| N/2+化合物B | 103.5 |
| N/2+化合物C | 104.6 |
a)对比试验，非本发明，不含助剂。
在两个试验中，化合物A给出了相对于单独半剂量(N/2)的显著N/2改善。化合物C和化合物B在小麦上给出了最好的效果，其给出了相对于单独半剂量(N/2)的显著N/2改善。该差异在统计学上是显著的。
实施例3—合成
通过使醇R3-OH与氧化乙烯和/或氧化丙烯在碱性催化剂存在下反应，且随后使烷氧基化醇与1,2-氧化癸烯在KOH存在下反应而合成通式(II)的羟烷基聚氧化烯二醇醚化合物1-7：
R1-CH(OH)-CH2-[O-R2a]x-[O-R2b]y-[O-R2c]Z-O-R3 (II)
其中基团如表3所定义。
表3
| 化合物 | R1 | R2a(x) | R2b(y) | R2c(z) | R3 |
| 1 | 辛基 | 亚丙基(1,5) | 亚乙基(16) | (0) | C12/14烷基 |
| 2 | 辛基 | 亚乙基(14) | 亚丙基(1) | (0) | C12/14烷基 |
| 3 | 辛基 | 亚丙基(3) | 亚乙基(16) | (0) | C12/14烷基 |
| 4 | 辛基 | 亚乙基(8) | 亚丙基(3) | 亚乙基(8) | C12/14烷基 |
| 5 | 辛基 | 亚丙基(3) | 亚乙基(14) | (0) | C11烷基a) |
| 6 | 辛基 | 亚乙基(2) | (0) | (0) | 2-乙基己基 |
| 7 | 辛基 | 亚乙基(5) | (0) | (0) | 2-丙基庚基 |
a)直链和支化烷基的混合物
实施例4—提高的吸收率
将小麦植株(普通小麦品种Melon)在温室中栽培6周直至发育阶段BBCH 39。将所述植株转移至自动实验室牵引喷雾器中，然后将它们用125g/ha氧唑菌、125g/ha氟唑菌酰胺和250g/ha相应化合物1-5根据如下参数喷雾：
在喷雾后，将所述植株再次在温室中在环境条件下栽培。在8天后，剪掉10-15片经处理的叶片试样并称量。
将叶片剪成小片，转移至玻璃瓶中，并用作为清洗介质的50％于软化水中的甲醇清洗5分钟。然后，将清洗介质与叶片分离。将叶片再次用清洗介质清洗5分钟。将两种清洗介质合并且稀释以用于分析。
最后，将叶片转移至含有提取介质(75％甲醇、20％水和5％HCl)的小瓶中，并使用Polytron PT 6100分散单元(Kinematica，CH)均化2分钟。将10ml提取物以4000rpm离心5分钟。将2ml上清液用2ml NaOH(0.2mol/L)和5ml环己烷处理，并搅拌30分钟，随后离心。将1ml环己烷相转移至玻璃小瓶中并干燥(德国Liebisch，N2蒸发器)。将残余物溶于甲醇/水50:50中，并借助HPLC-MS/MS分析。
使用Agilent 1100系列HPLC，其与装备有电喷雾离子化源的Applied BiosystemsAPI 3000三重四极杆质谱仪联用。所述质谱仪以MS/MS正离子模式使用多反应监测(MRM)运行，其中在优化条件下每种分析物使用两次跃迁(transition)。此外，将未喷雾的植株以相同方式处理以观察其是否被污染。将未喷雾的叶片用标准活性成分掺料以确定在清洗和提取步骤中的活性成分回收率。根据该回收率校正测得的试样值。结果汇总在表4中。
为了进行对比，不用化合物1-5喷雾植株。
数据表明，当使用本发明的化合物1-5时，氧唑菌和氟唑菌酰胺的吸收率提高。
表4：吸收率
| 化合物 | 氧唑菌吸收率[％] | 氟唑菌酰胺吸收率[％] |
| _a) | 19 | 16 |
| 1 | 43 | 30 |
| 2 | 41 | 27 |
| 3 | 41 | 29 |
| 4 | 40 | 27 |
| 5 | 39 | 27 |
a)不含任何助剂的对比实施例
实施例5-提高的生物学活性
在温室中在小麦(品种“Kanzler”)上评价生物学活性，所述小麦在2叶阶段被小麦叶锈菌(Puccinia triticina)侵染，并在高湿度下培育3天。将所述植株用包含50ppm(10g/ha或2.5g/ha剂量率)氧唑菌和100ppm(20g/ha)相应化合物1-7的组合物喷雾(喷雾体积200L/ha)。在对比实施例中，不添加助剂。将所述植株在20-24℃和60-90％相对湿度下进一步培育10天。最后，视觉检查侵染叶片面积(脓疱)的百分比。各值基于三次重复。结果汇总在表5中。
表5
a)不含助剂的对比实施例
实施例6—表面张力
使用化合物1-7于去离子水中的1g/l试样的溶液或分散体进行物理测量。静态或平衡表面张力是配制剂在喷雾溶液中的界面活性的特征值。在低于临界胶束浓度(CMC)下，静态表面张力取决于配制剂中的表面活性成分的浓度，而在高于CMC下，静态表面张力保持恒定。该测量使用过程张力计Kruess K 100使用Wilhelmy-Plate方法进行。在测量期间，用待分析的液体润湿垂直悬挂的铂盘底线。测量该盘被拉入液体时的力，且可将其换算成液体的表面张力(mN/m)。将40ml制得的喷雾溶液充入所述装置的Teflon槽中，并检测表面张力。在连续5个测量点相差小于0.1mN/m后，计算静态表面张力。结果汇总在表6中。
表6
| 化合物 | 表面张力[mN/m] |
| 1 | 29 |
| 2 | 29 |
| 3 | 29 |
| 4 | 30 |
| 5 | 29 |
| 6 | 28 |
| 7 | 27 |
实施例7—溶解性
为了测定溶解性，将化合物1-7的试样在室温下在获自ExxonnMobil的200(芳烃溶剂，初沸点约230℃)，或AMD10(N,N-二甲基癸酰胺)中搅拌，并视觉检查。
表7
Claims (17)
1.一种组合物，其包含农药和通式(I)的羟烷基聚氧化烯二醇醚：
其中：
R1为具有6-18个碳原子的饱和或不饱和、直链或支化烷基；
R2为亚乙基、亚丙基、亚丁基或其混合物；
R3为具有6-18个碳原子的饱和或不饱和、直链或支化烷基；且
n具有1-100的值。
2.根据权利要求1的组合物，其中所述羟烷基聚氧化烯二醇醚具有通式(II)：
R1-CH(OH)-CH2-[O-R2a]x-[O-R2b]y-[O-R2c]Z-O-R3 (II)
其中：
R1和R3如权利要求1所定义；
R2a、R2b和R2c独立地为亚乙基、亚丙基或亚丁基；
x、y和z独立地为0-100的值；且
x、y和z加和为1-100的值。
3.根据权利要求1或2的组合物，其中R1为具有8-14个碳原子的饱和或不饱和、直链或支化烷基。
4.根据权利要求1-3中任一项的组合物，其中R1为具有8-12个碳原子的饱和直链烷基。
5.根据权利要求1-4中任一项的组合物，其中R2为亚乙基或亚乙基与亚丙基的混合物。
6.根据权利要求1-5中任一项的组合物，其中R2为亚乙基。
7.根据权利要求1-6中任一项的组合物，其中R3为具有8-12个碳原子的饱和或不饱和、直链或支化烷基。
8.根据权利要求1-7中任一项的组合物，其中R3为具有8-12个碳原子的饱和支化烷基。
9.根据权利要求1-8中任一项的组合物，其中n具有3-50的值。
10.根据权利要求2-9中任一项的组合物，其中R2a、R2b和R2c独立地为亚乙基或亚丙基。
11.根据权利要求2-10中任一项的组合物，其中x、y和z加和为3-50的值。
12.根据权利要求1-11中任一项的组合物，其中所述农药包含至少一种杀真菌剂。
13.根据权利要求12的组合物，其中所述杀真菌剂选自羧酰胺类、三唑类、吡唑-4-羧酰胺类和嗜球果伞素类。
14.一种制备如权利要求1-13中任一项所定义的组合物的方法，包括使所述农药与通式(I)的羟烷基聚氧化烯二醇醚接触。
15.一种控制植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法，其中使如权利要求1-13中任一项所定义的组合物作用于相应害虫、其环境或待保护以防相应害虫的作物上、作用于土壤上和/或作用于不希望的植物和/或作物和/或其环境上。
16.包含如权利要求1-13中任一项所定义的组合物的种子。
17.如权利要求1-11中任一项所定义的羟烷基聚氧化烯二醇醚作为含农药的喷雾混合物中的助剂的用途。
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- 2015-05-04 ES ES15718952T patent/ES2836742T3/es active Active
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| ES2836742T3 (es) | 2021-06-28 |
| AU2015257857A1 (en) | 2016-11-17 |
| JP2017518968A (ja) | 2017-07-13 |
| EP3139740B1 (en) | 2020-09-16 |
| EP3139740A1 (en) | 2017-03-15 |
| BR112016025727B1 (pt) | 2021-11-30 |
| RU2016147550A (ru) | 2018-06-07 |
| CA2946341C (en) | 2023-09-26 |
| US20180064104A9 (en) | 2018-03-08 |
| US10694742B2 (en) | 2020-06-30 |
| CA2946341A1 (en) | 2015-11-12 |
| IL248440B (en) | 2020-10-29 |
| BR112016025727A2 (pt) | 2017-08-15 |
| RU2016147550A3 (zh) | 2019-02-15 |
| CN106455555B (zh) | 2021-03-12 |
| WO2015169711A1 (en) | 2015-11-12 |
| JP6708557B2 (ja) | 2020-06-10 |
| RU2704450C2 (ru) | 2019-10-28 |
| IL248440A0 (en) | 2016-12-29 |
| US20170099834A1 (en) | 2017-04-13 |
| AU2015257857B2 (en) | 2019-01-17 |
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