CN103501597B - 包含农药和缩醛溶剂的组合物 - Google Patents
包含农药和缩醛溶剂的组合物 Download PDFInfo
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- CN103501597B CN103501597B CN201280020949.7A CN201280020949A CN103501597B CN 103501597 B CN103501597 B CN 103501597B CN 201280020949 A CN201280020949 A CN 201280020949A CN 103501597 B CN103501597 B CN 103501597B
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- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
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- A—HUMAN NECESSITIES
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Abstract
本发明涉及一种包含农药和如下所述的式(B)的溶剂的农化组合物。此外，本发明涉及一种通过使该农药和溶剂彼此接触而制备该组合物的方法；式(B)的溶剂作为农药用溶剂的用途；防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法，其中使该组合物作用于相应有害物、其栖息地或待防止相应有害物的植物、土壤和/或不希望的植物和/或有用植物和/或其生长地。本发明进一步涉及包含该组合物的种子。
Description
本发明涉及一种包含农药和如下所述的式(B)的溶剂的农化组合物。此外，本发明涉及一种通过使该农药和溶剂接触而制备该组合物的方法；式(B)的溶剂作为农药用溶剂的用途；防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法，其中使该组合物作用于相应有害物、其环境或待防止相应有害物的植物、土壤和/或不希望的植物和/或农作物和/或其环境；以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。
WO2001/17345公开了一种包含生物活性化合物和缩醛溶剂的组合物。
包含缩醛的已知农化组合物的缺点尤其是不可能溶解高农药浓度。另一缺点是缩醛有臭味，具有低闪点、高粘度、高毒性和在水中的高溶解性。本发明的目的是要提供一种包含农药的组合物，该组合物克服了这些缺点。
该目的由一种包含农药和式(B)的溶剂的组合物，尤其是农化组合物实现：
其中
R1和R2相互独立地为C1-C20烷基或一起为C2-C14亚烷基，
R4为氢、C1-C20烷基、C1-C30芳基、C1-C30烷芳基或C1-C30芳烷基，其中碳原子可以任选被含杂原子的基团取代，
R5为单键或可以任选被含杂原子的基团取代和/或具有掺入C1-C6亚烷基链中的杂原子的C1-C6亚烷基，
AR为芳族基团，
SUB相互独立地为含杂原子的基团，以及
n为1-5的值。
R1和R2可以相互独立地为C1-C20烷基，其中烷基可以为线性或支化的。优选为线性的。R1和R2通常为脂族的。R1和R2通常未被取代。优选R1和R2相同。R1和R2优选相互独立地为C1-C12烷基，尤其优选C1-C8烷基，具体优选C1-C4烷基(如甲基、乙基、正丙基、异丙基、正丁基、异丁基)。具体而言，R1和R2均为甲基、乙基或正丙基，尤其是甲基或乙基，具体为甲基。
R1和R2可以一起为C2-C14亚烷基。此时R1和R2形成环状缩醛基团。该C2-C14亚烷基通常为脂族的。C2-C14亚烷基通常未被取代。优选R1和R2一起为C2-C8亚烷基，尤其优选C2-C4亚烷基，具体为亚乙基、亚正丙基或亚异丙基。
R4优选为氢、C1-C20烷基、C1-C30芳基、C1-C30烷芳基或C1-C30芳烷基，其中碳原子可以任选被至少一个C1-C20烷氧基取代。R4尤其优选为氢或C1-C12烷基，尤其是氢或甲基，非常具体为氢。
R5优选为单键或C1-C6亚烷基，尤其优选单键。
AR为具有n个取代基SUB的芳族基团。AR优选为具有n个取代基SUB的苯基或萘基。AR尤其优选为具有n=1-3个取代基SUB的苯基，其中n尤其为1。
SUB相互独立地为至少一个有机基团，其中n表示每个AR单元的这些基团数目。SUB的实例是包含卤化物、羧酸酯、烷氧基化物、羧酰胺、烷基、芳基、烷芳基、芳烷基、氰化物、硝酸酯、酮、硫酸酯、磺酸酯、磷酸酯、膦酸酯的有机基团。
优选SUB为至少一个C1-C20烷氧基，尤其是-O-R3。R3可以为C1-C20烷基，其中烷基可以为线性或支化的。优选为线性的。R3通常为脂族的。R3通常未被取代。R3优选为C1-C12烷基，尤其优选C1-C8烷基，具体优选C1-C4烷基(如甲基、乙基、正丙基、异丙基、正丁基、异丁基)。R3尤其为甲基。
在进一步优选的形式中，SUB为至少一个(优选正好一个)烷基。烷基优选为C1-C20烷基，尤其优选C1-C12烷基，具体为C1-C6烷基，如甲基或叔丁基。其中SUB为烷基的式(B)的溶剂实例是下列结构(B1)和(B2)：
具体合适的结构(B1)和(B2)是其中R1和R2均为甲基的那些。
取代基SUB可以以各种结构，如以邻位、间位或对位结构存在于芳族环AR上。它优选以对位结构存在。
指数n优选具有1-3的值，尤其优选1或2的值，尤其是1。
在优选形式中，R5为单键，AR为苯基或萘基且n为1或2的值。在尤其优选的形式中，R5为单键，AR为苯基或萘基，n为1或2的值，SUB为-O-R3且R4为氢或甲基。
式(B)或式(A)的溶剂的合适实例是下列结构(1)-(15)：
具体合适的结构(12)是其中R1和R2均为甲基的那些。
在具体优选的实施方案中，该溶剂为式(A)的溶剂：
其中R1和R2相互独立地为C1-C20烷基或一起为C2-C14亚烷基，且R3为C1-C20烷基。
在式(A)中，R1和R2可以相互独立地为C1-C20烷基，其中烷基可以为线性或支化的。优选为线性的。R1和R2通常为脂族的。R1和R2通常未被取代。优选R1和R2相同。优选R1和R2相互独立地为C1-C12烷基，特别优选C1-C8烷基，尤其优选C1-C4烷基(如甲基、乙基、正丙基、异丙基、正丁基、异丁基)。R1和R2尤其均为甲基、乙基或正丙基，尤其是甲基或乙基，具体为甲基。
在式(A)中，R1和R2可以一起为C2-C14亚烷基。此时R1和R2形成环状缩醛基团。C2-C14亚烷基通常为脂族的。C2-C14亚烷基通常为线性或支化的。C2-C14亚烷基通常不含包含杂原子的取代基。优选R1和R2一起为C2-C8亚烷基，尤其优选C2-C5亚烷基，具体为亚乙基、亚正丙基、亚异丙基(如-CH2-CH(CH3)-)、亚异丁基(如-CH2-CH(CH3)2-)或亚异戊基(如-CH2-C(CH3)2-CH2-)，非常具体为亚乙基、亚正丙基或亚异丙基(如-CH2-CH(CH3)-)。
在式(A)中，R3可以为C1-C20烷基，其中烷基可以为线性或支化的。优选为线性的。R3通常为脂族的。R3通常未被取代。优选R3为C1-C12烷基，特别优选C1-C8烷基，尤其优选C1-C4烷基(如甲基、乙基、正丙基、异丙基、正丁基、异丁基)。R3尤其为甲基。
式(A)的溶剂可以以邻位、间位或对位结构存在。它优选以对位结构存在。
在式(A)中，R1和R2相互独立地优选为C1-C4烷基，或者一起为C2-C6亚烷基，以及R3为C1-C4烷基。尤其优选R1、R2和R3为甲基。
具体合适的式(A)的溶剂是式A1、A2或A3的那些，最优选式A1。
式(B)(尤其是式(A))的溶剂通常在20℃下在水中的溶解度为不超过1.0重量%，优选不超过0.5重量%，尤其优选不超过0.1重量%。
式(B)(尤其是式(A))的化合物通常为已知的且可市购，例如对茴香醛二甲缩醛。式(B)(尤其是式(A))的缩醛可以通过常规方法制备，例如通过使烷氧基取代的苯甲醛与醇反应而制备。
本发明组合物通常基于该组合物包含至少10重量%，优选至少20重量%，尤其优选至少30重量%式(B)(尤其是式(A))的溶剂。在大多数情况下，该组合物包含不超过95重量%，优选不超过90重量%，尤其优选不超过80重量%的式(B)(尤其是式(A))的溶剂。
式(B)(尤其是式(A))的溶剂通常包含该农药，后者就此而言可以以固体、溶解、悬浮和/或乳化形式存在。优选式(B)(尤其是式(A))的溶剂以溶解形式包含该农药。
农化组合物通常理解为指包含农药且可以在防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法中使用的组合物，其中使该组合物作用于相应有害物、其环境或要防止相应有害物的植物、土壤和/或不希望的植物和/或有用植物和/或其环境。
表述农药涉及至少一种选自杀真菌剂、杀虫剂、杀线虫剂、除草剂、安全剂和/或生长调节剂的活性物质。优选的农药是杀真菌剂、杀虫剂和除草剂，尤其是杀真菌剂和除草剂。还可以使用上述类别中两种或更多种农药的混合物。熟练技术人员熟知该类农药，它们例如可以在PesticideManual，第14版(2006)，TheBritishCropProtectionCouncil，London中找到。合适的杀虫剂是选自如下类别的杀虫剂：氨基甲酸酯类、有机磷酸酯类、有机氯杀虫剂、苯基吡唑类、合成除虫菊酯类、新类烟碱类、斯皮诺素类(spinosins)、阿维菌素类(avermectins)、米尔霉素类(milbemycins)、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、二酰基肼类、METI杀螨剂以及杀虫剂如氯化苦(chloropicrin)、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid)、四螨嗪(clofentezine)、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)、二硝酚(DNOC)、噻嗪酮(buprofezin)、灭蝇胺(cyromazine)、双甲脒(amitraz)、灭蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、fluacrypyrim、鱼藤酮(rotenon)或其衍生物。合适的杀真菌剂是选自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、抗生素类、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、羧酸酰胺类、氯代腈类、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、羟基酰替苯胺类、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、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、氨磺酰三唑类、噻唑羧酰胺类、硫代氨基甲酸酯类、托布津类(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。合适的除草剂是选自如下类别的除草剂：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、苯甲酸类、苯并噻二嗪酮类、联吡啶氨基甲酸酯类、氯代乙酰胺类、氯代羧酸、环己烷二酮类、二硝基苯胺类、二硝基苯酚类、二苯基醚类、甘氨酸类、咪唑啉酮类、异唑类、异唑烷酮类、腈类、N-苯基苯邻二甲酰亚胺类、二唑类、唑烷二酮类、羟乙酰胺类、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、三唑并羧酰胺类、三唑并嘧啶类、三酮类、尿嘧啶类、脲类。
该农药通常在20℃下在式(B)(尤其是式(A))的溶剂中以至少10g/L，优选至少30g/L，尤其优选至少50g/L可溶。
该农药通常在20℃下在水中以不超过10g/L，优选不超过1g/L，尤其优选不超过0.1g/L可溶。
本发明组合物还可以包含其他农药。其他农药可以以溶解、悬浮和/或乳化形式存在。
在另一实施方案中，该农药以溶解形式存在于液体农化组合物中。优选该农药在20℃下基于该农药以至少90重量%，优选至少98重量%溶解于该溶剂体系中。
在另一实施方案中，至少一种农药基于该农药至少90重量%以固体颗粒形式悬浮于该溶剂体系中。若该组合物包含至少两种农药，则至少一种农药至少90重量%溶解于该溶剂体系中。优选该农药至少95重量%，尤其优选至少98重量%悬浮于该溶剂体系中。
本发明组合物基于该组合物通常包含0.1-70重量%，优选1-50%，尤其是3-30重量%农药。
本发明组合物包含配制助剂，助剂的选择通常取决于具体实施方案和/或活性物质。合适配制助剂的实例是额外的溶剂、表面活性剂和其他表面活性物质(如加溶剂、保护性胶体、润湿剂和粘合剂)，辅助剂，有机和无机增稠剂，杀菌剂，防冻剂，消泡剂，着色剂和粘着剂(例如用于种子处理)。
除了式(B)的溶剂外可以存在于该组合物中的合适额外溶剂是有机溶剂如中至高沸点的矿物油馏分如煤油和柴油，此外还有煤焦油和植物或动物来源的油，脂族、脂环族和芳族烃类，例如石蜡、四氢萘、烷基化萘及其衍生物、烷基化苯及其衍生物，醇类如乙醇、丙醇、丁醇、苄醇和环己醇，二醇，酮类如环己酮、γ-丁内酯，二甲基脂肪酸酰胺，脂肪酸和脂肪酸酯，以及强极性溶剂，例如胺类，如N-甲基吡咯烷酮。原则上还可以使用溶剂混合物。优选向本发明组合物中加入不超过40重量%，优选不超过20重量%的额外溶剂，在每种情况下基于该组合物。
表面活性剂可以单独或作为混合物使用。表面活性剂为降低水的表面张力的化合物。合适的表面活性剂是阴离子、阳离子、非离子和两性表面活性剂，嵌段聚合物和聚电解质。本发明组合物优选包含至少一种阴离子表面活性剂。
合适的阴离子表面活性剂是磺酸、硫酸、磷酸或羧酸的碱金属、碱土金属或铵盐。磺酸盐的实例是烷基芳基磺酸盐、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、乙氧基化芳基酚的磺酸盐、缩合萘的磺酸盐、十二烷基-和十三烷基苯的磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例是脂肪酸和油的硫酸盐、乙氧基化烷基酚的硫酸盐、醇的硫酸盐、乙氧基化醇的硫酸盐或脂肪酸酯的硫酸盐。磷酸盐的实例是磷酸盐酯。羧酸盐的实例是烷基羧酸盐和羧化醇或烷基酚乙氧基化物。优选的阴离子表面活性剂是乙氧基化芳基酚的磺酸盐，尤其是磷酸化或硫酸化二-和/或三苯乙烯基苯基烷氧基化物，例如如WO2007/110355第3页第30行至第5页第11行所述。
合适的非离子表面活性剂是烷氧基化物，N-烷基化脂肪酸酰胺，胺氧化物，酯或糖基表面活性剂。烷氧基化物的实例是诸如已经烷氧基化的醇、烷基酚、胺、酰胺、芳基酚、脂肪酸或脂肪酸酯的化合物。氧化乙烯和/或氧化丙烯可以用于烷氧基化，优选氧化乙烯。N-烷基化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。酯的实例是脂肪酸酯、甘油酯或甘油单酯。糖基表面活性剂的实例是脱水山梨醇、乙氧基化脱水山梨醇、蔗糖和葡萄糖酯或烷基聚葡糖苷。
合适阳离子性表面活性剂是季表面活性剂，例如具有一个或两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是烷基甜菜碱和咪唑啉类。合适的嵌段聚合物是包含聚氧乙烯和聚氧丙烯的嵌段的A-B或A-B-A类型嵌段聚合物或包含链烷醇、聚氧乙烯和聚氧丙烯的A-B-C类型嵌段聚合物。合适的聚电解质是聚酸或聚碱。聚酸的实例是聚丙烯酸的碱金属盐。聚碱的实例是聚乙烯基胺或聚乙烯胺。
本发明组合物可以包含各种量的表面活性剂。它可以基于该组合物的总量包含0.1-40重量%，优选1-30重量%，尤其是2-20重量%的表面活性剂总量。
辅助剂的实例是有机改性的聚硅氧烷如BreakThruS醇烷氧基化物，如245、MBA1303、LF和ON；EO/PO嵌段聚合物，例如RPE2035和B；醇乙氧基化物，例如XP80；以及磺基琥珀酸二辛酯钠，例如RA。
增稠剂(即赋予该组合物以改性的流动行为，即静止时的高粘度和运动时的低粘度的化合物)的实例是多糖以及有机和无机层状矿物如黄原胶CPKelco)，23(Rhodia)或(R.T.Vanderbilt)或(EngelhardCorp.)。
可以加入杀菌剂以稳定该组合物。杀菌剂的实例是基于双氯酚和苄醇半缩甲醛的那些(ICI的或ThorChemie的RS以及Rohm&Haas的MK)以及基于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的那些(ThorChemie的MBS)。
合适防冻剂的实例是乙二醇、丙二醇、尿素和甘油。
消泡剂实例是聚硅氧烷乳液(例如SRE，德国Wacker或法国Rhodia)，长链醇，脂肪酸，脂肪酸盐，有机氟化合物及其混合物。
着色剂的实例是微水溶性颜料和水溶性染料二者。可以提到的实例是由如下名称已知的染料和颜料：若丹明B、C.I.颜料红112和C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
粘着剂的实例是聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤维素醚(日本Shin-Etsu)。
本发明组合物通常以农化配制剂形式存在。合适的农化配制剂是水溶性浓缩物(SL，LS)，可再分散性浓缩物(DC)，可乳化浓缩物(EC)，乳液(EW，EO，ES，ME)，悬浮液(SC，OD，FS)，悬浮乳液(SE)以及粉末和颗粒(WP，WG)。
优选该组合物以可乳化浓缩物、乳液、悬浮液(如OD，FS)、悬浮乳液、粉末或颗粒形式存在。在进一步优选的实施方案中，该组合物以WG配制剂形式存在，例如如WO2007/028505或WO2007/028504所述。
在大多数情况下，在施用之前稀释本发明组合物以制备所谓的桶混物。适合稀释的物质是中到高沸点的矿物油馏分，如煤油或柴油，此外还有煤焦油和植物或动物来源的油，脂族、环状和芳族烃，例如甲苯、二甲苯、石蜡、四氢萘、烷基化萘或其衍生物，甲醇、乙醇、丙醇、丁醇、环己醇、环己酮、异佛尔酮，强极性溶剂，例如二甲亚砜、N-甲基吡咯烷酮或水。优选使用水。稀组合物通常通过喷雾或雾化施用。各种类型的油、润湿剂、辅助剂、除草剂、杀菌剂、杀真菌剂可以在紧临使用前加入该桶混物中(桶混合)。这些试剂通常可以与本发明组合物以1:100-100:1，优选1:10-10:1的重量比混合。在桶混物中的农药浓度可以在相当大的范围内变化。它们通常为0.0001-10%，优选0.01-1%。当用于植物保护中时，施用率取决于所需效果的性质为0.01-2.0kg/ha活性物质。
本发明还涉及本发明组合物在防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长中的用途，其中使该组合物作用于相应有害物、其环境或要防止相应有害物的植物、土壤和/或不希望的植物和/或有用植物和/或其环境。此外，本发明涉及本发明组合物在防治植物上不希望的昆虫或螨虫侵袭和/或防治植物病原性真菌和/或防治不希望的植物生长中的用途，其中用该组合物处理有用植物的种子。
此外，本发明涉及已经用本发明组合物处理的种子。优选该种子已经用本发明组合物拌种。拌种意味着种子已经用该组合物处理且该组合物保留在种子上。该组合物可以以未稀释形式或者优选以稀释形式施用于种子上。此时可以将所述组合物稀释2-10倍，从而使得待用于拌种的组合物中存在0.01-60重量%，优选0.1-40重量%农药。施用可以在播种之前进行。植物繁殖材料的处理，尤其是种子的处理对熟练技术人员而言是已知的且通过撒粉、包衣、造粒、浸渍或浸泡植物繁殖材料进行，其中该处理优选通过造粒、包衣和撒粉进行，从而例如防止种子的早期萌发。在种子处理中，通常使用1-1000g/100kg，优选5-100g/100kg繁殖材料或种子的农药量。
此外，本发明涉及一种制备本发明组合物的方法，其中使该农药和式(B)(尤其是式(A))的溶剂接触，例如混合。优选的式(B)的溶剂和溶剂如上所述。混合通过常规混合方法，如搅拌、振摇或任何其他能量输入进行。可以以常规量加入用于制备农化配制剂的其他辅助剂。合适配制助剂的实例如上所述。
本发明还涉及式(B)的溶剂作为农药用溶剂的用途，例如在农化配制剂中作为农药用溶剂的用途。优选的式(B)的溶剂如前所述。农化配制剂对熟练技术人员而言是已知的。它们通常包含农药和任选地包含用于农化配制剂的辅助剂，例如用于农化配制剂的上述辅助剂。
本发明还涉及式(B)的溶剂在农化组合物中的用途，例如作为配制助剂，例如用于农化配制剂的上述辅助剂。
本发明的优点尤其是可以将高浓度的农药溶于式(B)(尤其是式(A))的溶剂中。式(B)(尤其是式(A))的溶剂可以由已知材料开始以简单且廉价方式以工业规模制备。茴香醛二甲缩醛尤其可以以大工业规模得到。式(B)(尤其是式(A))的溶剂的另一优点是它们的臭味非常低；它们的闪点非常高；它们的低粘度；它们的低毒性和它们的低水溶性。这些优点非常重要，从而使得式(B)(尤其是式(A))的溶剂可以由农夫安全使用，由此可以提供有利的农化配制剂。
下列实施例说明本发明而不施加任何限制。
实施例
苯甲醛二甲缩醛(非本发明)：由AcrosOrganics市购，>98重量%，CAS号1125-88-8。
对茴香醛二甲缩醛(4-甲氧基苯甲醛二甲缩醛)：由AcrosOrganics市购，>98重量%，CAS号2186-92-7。
实施例1—农药溶解度
A)在20℃下将唑菌胺酯(pyraclostrobin)在搅拌下加入苯甲醛二甲缩醛或对茴香醛二甲缩醛中。在这两种情况下观察到唑菌胺酯溶解度为至少50重量%。
B)在20℃下炔草酯(Clodinafop-propargyl)和解草酯(cloquintocet-mexyl)(重量比4:1)在搅拌下加入苯甲醛二甲缩醛或对茴香醛二甲缩醛中。在这两种情况下可以制备浓度为至少50重量%的溶液。
C)在20℃下测定除草剂1,5-二甲基-6-硫代-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)-1,3,5-三嗪烷(triazinan)-2,4-二酮的最大溶解度，测得在200ND(具有>99重量%芳烃的芳族溶剂混合物；沸程235-290℃)中为63g/L，在150ND(具有>99重量%芳烃的芳族溶剂混合物；沸程179-194℃)中为19g/L以及在对茴香醛二甲缩醛中为214g/L。
实施例2—在水中的溶解度
分析苯甲醛二甲缩醛或对茴香醛二甲缩醛在20℃下在水中的溶解度。在两种情况下不能在水中溶解超过0.1重量%。
实施例3—气味
在涉及3个人的盲试中比较苯甲醛二甲缩醛或对茴香醛二甲缩醛的气味。
苯甲醛二甲缩醛具有刺鼻气味。安全数据单将该气味描述为“强烈金属状杏仁味”。
对茴香醛二甲缩醛具有淡淡的气味。来自AcrosOrganics(2009年7月20日最新更新)的安全数据单将该气味描述为“令人愉悦的气味”或“花香”(在来自2010年12月22日最新更新的TCIEuropeNV的安全数据单中)。
实施例4—毒性
根据欧盟(theEuropeanUnion)如EU指引67/548/EEC、1999/45/EC或88/379/EEC中所述，苯甲醛二甲缩醛被分类为“Xn—有害”和“R22—吞咽时有害”。相比之下，对茴香醛二甲缩醛根据相同指引没有被分类且没有R措辞。
实施例5—闪点
苯甲醛二甲缩醛的闪点为69℃。对茴香醛二甲缩醛的闪点为114℃(如DIN53213-1所述测量)。
实施例6—粘度
对茴香醛二甲缩醛在20℃下的粘度为5.5mPas。
实施例7—液体农化配制剂
在室温下将40g炔草酯和10g解草酯搅入10gDSS/7(乙氧基化多芳基苯酚的硫酸铵，由Rhodia市购)在对茴香醛二甲缩醛中的混合物中并用对茴香醛二甲缩醛配成100mL。如此得到的乳液浓缩物(EC)在用标准水CIPAC-D稀释(1重量%)时显示出良好的乳化行为。
实施例8—固体农化配制剂
将40g实施例7的乳液浓缩物吸收到30g50S(比表面积为475m2/g，平均粒度为7.5μm的硅石粉末)上。将所得被吸收物质与120g珍珠岩、25g萘磺酸盐缩合物的钠盐，5gOT-B(阴离子表面活性剂)和1g含聚硅氧烷的消泡剂混合。在用空气射流研磨之后，用5重量%水将该混合物制成糊并在实验室挤出机(孔直径0.8mm)中造粒。在干燥之后得到具有良好稳定性和良好分散性能的颗粒。
Claims (23)
1.一种包含农药和式(A)的溶剂的农化组合物：
其中R1和R2相互独立地为C1-C4烷基或一起为C2-C6亚烷基且R3为C1-C8烷基，以及其中所述农药在20℃下在水中以不超过10g/L可溶。
2.根据权利要求1的组合物，其中R3为C1-C4烷基。
3.根据权利要求1的组合物，其中R1、R2和R3为甲基。
4.根据权利要求2的组合物，其中R1、R2和R3为甲基。
5.根据权利要求1-4中任一项的组合物，其中所述溶剂具有对位结构。
6.根据权利要求1-4中任一项的组合物，包含至少10重量％所述溶剂。
7.根据权利要求5的组合物，包含至少10重量％所述溶剂。
8.根据权利要求1-4中任一项的组合物，包含阴离子表面活性剂。
9.根据权利要求7的组合物，包含阴离子表面活性剂。
10.根据权利要求1-4中任一项的组合物，其中所述溶剂在20℃下在水中的溶解度为不超过1.0重量％。
11.根据权利要求9的组合物，其中所述溶剂在20℃下在水中的溶解度为不超过1.0重量％。
12.根据权利要求1-4中任一项的组合物，其中所述溶剂以溶解形式包含所述农药。
13.根据权利要求11的组合物，其中所述溶剂以溶解形式包含所述农药。
14.根据权利要求1-4中任一项的组合物，包含以溶解、悬浮和/或乳化形式存在的其他农药。
15.根据权利要求13的组合物，包含以溶解、悬浮和/或乳化形式存在的其他农药。
16.根据权利要求1-4中任一项的组合物，其中所述农药在20℃下在所述溶剂中以至少10g/L可溶。
17.根据权利要求15的组合物，其中所述农药在20℃下在所述溶剂中以至少10g/L可溶。
18.根据权利要求1-4中任一项的组合物，包含20-95重量％所述溶剂。
19.根据权利要求17的组合物，包含20-95重量％所述溶剂。
20.一种制备根据权利要求1-19中任一项的组合物的方法，包括使所述农药和所述溶剂接触。
21.根据权利要求1-19中任一项的式(A)的溶剂在农化组合物中的用途。
22.一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法，其中使根据权利要求1-19中任一项的组合物作用于相应有害物、其环境或待防止相应有害物的植物、土壤和/或不希望的植物和/或农作物和/或其环境。
23.一种用根据权利要求1-19中任一项的组合物处理种子的方法，其中所述种子包含所述组合物。
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11164327.6 | 2011-04-29 | ||
| EP11164327 | 2011-04-29 | ||
| EP11166304 | 2011-05-17 | ||
| EP11166304.3 | 2011-05-17 | ||
| PCT/EP2012/057575 WO2012146623A1 (de) | 2011-04-29 | 2012-04-25 | Zusammensetzung enthaltend ein pestizid und ein acetalisches lösungsmittel |
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| Publication Number | Publication Date |
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| CN103501597A CN103501597A (zh) | 2014-01-08 |
| CN103501597B true CN103501597B (zh) | 2016-02-17 |
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| CN201280020949.7A Active CN103501597B (zh) | 2011-04-29 | 2012-04-25 | 包含农药和缩醛溶剂的组合物 |
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| EP (1) | EP2701502B1 (zh) |
| JP (1) | JP2014513090A (zh) |
| KR (1) | KR20140027331A (zh) |
| CN (1) | CN103501597B (zh) |
| AR (1) | AR086244A1 (zh) |
| BR (1) | BR112013027781B1 (zh) |
| WO (1) | WO2012146623A1 (zh) |
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| JP6290195B2 (ja) | 2012-06-13 | 2018-03-07 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 大環状ケトンの製造方法 |
| WO2023208447A1 (en) * | 2022-04-25 | 2023-11-02 | Basf Se | An emulsifiable concentrate having a (substituted) benzaldehyde-based solvent system |
Citations (5)
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|---|---|---|---|---|
| US3826822A (en) * | 1971-01-08 | 1974-07-30 | Pepro | Liquid insecticidal compositions for impregnation of solid supports for prolonged diffusion |
| EP0230773B1 (en) * | 1985-12-27 | 1990-05-23 | Sumitomo Chemical Company, Limited | Dipropargyloxybenzene compounds and their production |
| CN1106399A (zh) * | 1993-11-02 | 1995-08-09 | Basf公司 | 环状醛醚及其制备和在作物保护剂方面的应用 |
| WO1997034986A1 (en) * | 1996-03-22 | 1997-09-25 | The Procter & Gamble Company | Detergent compositions containing fragrance precursors and the fragrance precursors themselves |
| CN1372437A (zh) * | 1999-09-02 | 2002-10-02 | 科莱恩有限公司 | 生物活性化合物的生物可降解溶液 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5378468A (en) * | 1992-09-22 | 1995-01-03 | The Mennen Company | Composition containing body activated fragrance for contacting the skin and method of use |
| JP2002128610A (ja) * | 2000-10-17 | 2002-05-09 | Kao Corp | 抗菌抗カビ剤 |
| EP1947946A2 (de) | 2005-09-08 | 2008-07-30 | Bayer Cropscience Ag | Neue sulfonamid-haltige feste formulierungen |
| EA200801918A1 (ru) | 2006-03-24 | 2009-06-30 | Басф Се | Агрохимические препараты |
-
2012
- 2012-04-25 JP JP2014506848A patent/JP2014513090A/ja active Pending
- 2012-04-25 WO PCT/EP2012/057575 patent/WO2012146623A1/de active Application Filing
- 2012-04-25 KR KR1020137031290A patent/KR20140027331A/ko not_active Application Discontinuation
- 2012-04-25 CN CN201280020949.7A patent/CN103501597B/zh active Active
- 2012-04-25 EP EP12716450.7A patent/EP2701502B1/de active Active
- 2012-04-25 BR BR112013027781-5A patent/BR112013027781B1/pt active IP Right Grant
- 2012-05-02 AR ARP120101546A patent/AR086244A1/es unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3826822A (en) * | 1971-01-08 | 1974-07-30 | Pepro | Liquid insecticidal compositions for impregnation of solid supports for prolonged diffusion |
| EP0230773B1 (en) * | 1985-12-27 | 1990-05-23 | Sumitomo Chemical Company, Limited | Dipropargyloxybenzene compounds and their production |
| CN1106399A (zh) * | 1993-11-02 | 1995-08-09 | Basf公司 | 环状醛醚及其制备和在作物保护剂方面的应用 |
| WO1997034986A1 (en) * | 1996-03-22 | 1997-09-25 | The Procter & Gamble Company | Detergent compositions containing fragrance precursors and the fragrance precursors themselves |
| CN1372437A (zh) * | 1999-09-02 | 2002-10-02 | 科莱恩有限公司 | 生物活性化合物的生物可降解溶液 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2701502B1 (de) | 2015-08-05 |
| CN103501597A (zh) | 2014-01-08 |
| WO2012146623A1 (de) | 2012-11-01 |
| BR112013027781A2 (pt) | 2016-07-26 |
| JP2014513090A (ja) | 2014-05-29 |
| AR086244A1 (es) | 2013-11-27 |
| EP2701502A1 (de) | 2014-03-05 |
| KR20140027331A (ko) | 2014-03-06 |
| BR112013027781B1 (pt) | 2018-12-18 |
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