CN114466836A - 脱落酸的溶剂化物和含有脱落酸的液体组合物 - Google Patents
脱落酸的溶剂化物和含有脱落酸的液体组合物 Download PDFInfo
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- CN114466836A CN114466836A CN202080068360.9A CN202080068360A CN114466836A CN 114466836 A CN114466836 A CN 114466836A CN 202080068360 A CN202080068360 A CN 202080068360A CN 114466836 A CN114466836 A CN 114466836A
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- Prior art keywords
- abscisic acid
- methyl
- composition
- total weight
- solvate
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- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 title claims abstract description 316
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 title claims abstract description 147
- 239000000203 mixture Substances 0.000 title claims abstract description 138
- 239000012453 solvate Substances 0.000 title claims abstract description 72
- 239000007788 liquid Substances 0.000 title claims abstract description 49
- 238000009472 formulation Methods 0.000 claims abstract description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- -1 N-substituted pyrrolidones Chemical class 0.000 claims description 139
- 241000196324 Embryophyta Species 0.000 claims description 47
- 239000007921 spray Substances 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 33
- 239000012872 agrochemical composition Substances 0.000 claims description 31
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 18
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- JLIDBLDQVAYHNE-IBPUIESWSA-N (s)-(+)-Abscisic acid Natural products OC(=O)\C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-IBPUIESWSA-N 0.000 claims description 8
- 239000002535 acidifier Substances 0.000 claims description 8
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- 125000002791 glucosyl group Chemical class C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- HHDYPZVHXGPCRG-KYKYGANHSA-N abscisic acid mathyl ester Natural products COC(=O)C=C(C)/C=C/C1(O)C(=CC(=O)CC1(C)C)C HHDYPZVHXGPCRG-KYKYGANHSA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- HHDYPZVHXGPCRG-VEQVDCDKSA-N methyl (2z,4e)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate Chemical compound COC(=O)\C=C(\C)/C=C/C1(O)C(C)=CC(=O)CC1(C)C HHDYPZVHXGPCRG-VEQVDCDKSA-N 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 abstract description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 35
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 29
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
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- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 7
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- JLIDBLDQVAYHNE-QHFMCZIYSA-N (-)-abscisic acid Chemical class OC(=O)/C=C(/C)\C=C\[C@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-QHFMCZIYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 4
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- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 description 4
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- IAUMNRCGDHLAMJ-UHFFFAOYSA-N methyl 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 IAUMNRCGDHLAMJ-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明涉及脱落酸的新改性、脱落酸的液体组合物及其在农业化学应用中的用途。本发明的改性和组合物含有与至少一种N‑烷基吡咯烷酮呈溶剂化物形式的脱落酸,其中N‑烷基具有3至6个碳原子。这些溶剂化物使得制剂能够具有高浓度的脱落酸。
Description
本发明涉及脱落酸(abscisic acid)的新改性。本发明进一步涉及脱落酸的高载量液体组合物。
脱落酸(“ABA”)是天然存在的植物激素,其影响高等植物生长的所有阶段(Taiz等人(2015)Plant Physiology and Development.Sinauer Associates;Bruzzone等人(2012))。它也出现在苔藓、真菌和后生动物中,并且讨论了ABA在人类中的作用。可能受影响的主要植物生长过程包括控制种子发育、成熟和发芽,维持芽的休眠,加速果实成熟,激活病原体抗性响应防御,诱导已经受损的细胞及其邻近细胞的衰老,以及在耐受应激条件下(特别是缺乏足够的水)支持植物。(Taiz等人(2015)Plant Physiology andDevelopment.Sinauer Associates;Arteca,R.(1996),Plant Growth Substances:Principles and Applications.New York:Chapman&Hall;Mauseth,J.D.(1991),Botany:An Introduction to Plant Biology.Philadelphia:Saunders.pp.348-415;Raven,P.H.,Evert,R.F.,和Eichhorn,S.E.(1992),Biology of Plants.New York:Worth,pp.545-572)。
脱落酸的名称归功于这种植物生长调节剂在秋天直接导致落叶树的叶子脱落,后来发现其仅在少数植物物种中有效。脱落素和休眠素是先前用于这种植物激素的名称。脱落酸及其类似物的化学和生理学例如由Milborrow,Ann.Rev.Plant Physiol.1974,25,259-307进行了描述。脱落酸可以直接作为单一植物激素起作用,如在气孔口的控制中,或经由其他植物激素如赤霉酸或乙烯的平衡或诱导(Taiz等人(2015))。
脱落酸的天然存在的对映异构形式是(S)-(+)-脱落酸。在一些文献报道中,发现(R)-(-)-脱落酸对映异构体是生物学上无活性的。然而,其它研究表明(R)-(-)-脱落酸也具有一些生物学活性,但通常与(S)-(+)-对映异构体的生物学活性不同(Zeevart J.A.D.和Creelman,R.A.(1988)Metabolism and Physiology of Abscisic Acid,Annu.Rev.Plant Physiol.Plant Mol.Biol.39,439473)。
脱落酸是羧酸,因此在具有酸性pH值的介质中,它被质子化并处于其中性未解离形式。这种不带电的、未解离的形式比脱落酸的盐更亲脂,并且相对于在较高pH值下存在的带电、解离形式的脱落酸促进不带电的酸形式渗透到植物角质层中(Blumenfeld和Bukovac1972,Planta 107:261268;Schonherr和Baur(1994),Baur(1998))。脱落酸的不带电、未解离形式也比盐形式更容易从质外体穿过细胞膜进入胞质溶胶,而导致增强的摄取和优异的生物活性。一旦进入细胞,脱落酸就被解离,并且这种离子阱机制也允许脱落酸在韧皮部中长距离运输(Hartung和Slovik 1991)。
脱落酸在20世纪60年代早期被首次定义为生长抑制剂,其在脱落的棉花果实中和在光周期诱导成为休眠的梧桐树的叶片中积累(Finkelstein RR.Rock CD(2002),Abscisic acid biosynthesis and response,The Arabidopsis Book:第45卷,第1期,第1-48页)。从那时起,脱落酸已经显示出调节植物生长和发育的许多方面,包括胚成熟、种子休眠、发芽、细胞分裂和延伸等。尽管脱落酸在历史上被认为是生长抑制剂,但幼年组织具有高脱落酸水平,并且脱落酸缺陷型突变植物由于其减少蒸腾和建立膨压的能力受损而严重发育不良。外源脱落酸处理突变体恢复正常细胞扩展和生长。
脱落酸被认为通过与受体蛋白结合引发其对细胞的作用,尽管它们的本性和位置仍然在很大程度上未知。推定的受体(一种或多种)的激活引起一连串事件,导致离子通道的快速变化和基因转录模式的较慢变化。虽然已经识别了所述串事件的许多单独分量,但是尚未获得完整的图片。
市场上仅有少数包含脱落酸的商业制剂可在农业中用于各种目的,例如改进植物的应激耐受性(stress tolerance)、减慢其生长速率、调节开花期及其它目的。脱落酸也已被报道具有昆虫抑制性质(Visscher的美国专利号4,434,180和4,209,530)。粉末形式的脱落酸目前可从各种中国供应商商购获得,如江西的New Reyphon Biochemical Co.,Ltd和中国公司Lomon Biotechnology Company,Ltd.。在其它用途中,所述物质的典型主张是提高某些作物的产量和质量。Sumitomo和Valent Biosciences还提供含有脱落酸的商业产品。
与现有技术脱落酸制剂相关的一个限制是脱落酸在未缓冲水中的溶解度相对较差:在常温下将溶解不超过约3克/升(约0.3重量%)。约3000份/百万份(ppm)的浓度是在室温下在水中可达到的最高浓度。脱落酸在硬水中的溶解度甚至更低。
存在通过将脱落酸配制成盐来提高脱落酸的溶解度的现有技术。例如,US 8,278,480 B2描述了S(+)-脱落酸的盐和含有S-(+)-脱落酸的盐的组合物,其用于农业用途以改进脱落酸的溶解度。报道了溶解的脱落酸载量高达10重量%的水性制剂。然而,认为盐形式的活性低于不带电荷、未解离形式的脱落酸,后者比盐更容易穿过角质层。
获得现有技术中已知的较高载量液体制剂的另一种方法是将脱落酸配制成悬浮浓缩物。一个实例是来自Valent Biosciences的商业制剂BioNik,S-(+)-脱落酸浓度为250g/L(25重量%)的悬浮浓缩物,其用作种子处理剂以延迟种子萌芽。然而,作为悬浮浓缩物的制剂可能具有缺点,例如脱落酸在喷雾液体中缓慢溶解和晶体生长,这可能导致喷嘴堵塞。此外,由于制剂中的沉降或晶体生长,储存稳定性可能受到限制。总体而言,固体形式的脱落酸的活性较差。
脱落酸在一些有机溶剂中具有更好的溶解度,但脱落酸在许多有机溶剂中的液体制剂由于其物理化学性质如可燃性或挥发性而是不可接受的。此外,因为溶解所需的有机溶剂大大超过所施用的活性成分的量,所以归因于溶剂的潜在植物毒性或污染食品的可能性,合适溶剂的量进一步受到限制。
其它潜在的溶剂具有极性性质,如丙酮、乙醇、DMSO、甘醇或NMP(N-甲基-2-吡咯烷酮),但由于溶剂能力、闪点、生态毒性或胚胎毒性而受到限制。
此外,与脱落酸制剂的工业应用相关的问题之一是溶剂基脱落酸液体制剂的储存稳定性相对较差,植物中8'和9'甲基的羟基化失活(美国专利号6,004,905)和日光诱导的活性2-顺式,4-反式-S-(+)-脱落酸降解和异构化为非活性2-反式,4-反式-S-(+)-脱落酸异构体(Kamuro Y.1994.Plant and Chemical Regulation 29:155165.)。
脱落酸的粉末制剂是最常见的,这归因于有限的溶解度和因此更少稳定性问题,如上所述那样。WO 2008/094558 A2描述了具有改进的储存稳定性和光化学稳定性的S-(+)-脱落酸的固体制剂。商业制剂的一个实例是Protone,其是来自Sumitomo的20重量%可润湿颗粒制剂。然而,由于处理问题、粉尘形成和在喷雾液体中的缓慢溶解,使用浓缩液体溶液代替粉末通常更方便。对可变实际因素如水pH值和质量或温度的依赖性也更明显。因此,仍需要具有高载量的液体脱落酸制剂,其能够克服上述问题并且比酸本身更好地溶于水。
从经济角度来看,最大活性物质负载水平对于作物保护制剂是期望的。然而,归因于脱落酸的低溶解度和其它所述的限制,目前的商业制剂是最大载量为20重量%的固体或其中未溶解的脱落酸是以最大载量25重量%分散在水中的固体的悬浮浓缩物。已知溶解的脱落酸的液体商业制剂仅具有最大10重量%或更低的载量。
商业上重要的分子的不同改性物(包括无定形形式和结晶溶剂化物)通常具有不同的性能,这在不同背景中可能是有用的。因此,例如,结晶形式通常比无定形形式更稳定,使得它们可用于固体材料的长期储存,而无定形形式通常比结晶形式更容易溶解,因此对于某些目的而言,对于良好的生物利用率可能比结晶形式更有用。
化合物的晶体形式影响其理化性能,例如熔点、溶解度或溶解速率。因此,有利的是,具有一定范围的晶格能并因此具有一定范围的理化性能的晶体形式是可获得的,以致允许例如优化处理(例如农业(如植物处理)、兽医或药物处理)的有效性。因此,例如,在一些应用中,更稳定但较不可溶的形式可能是有利的,而在其它应用中,更高能量、更可溶的形式可以提供不同的一组优点。
因为脱落酸是生物活性剂,所以非常需要获得具有改进的溶解度和/或溶解速率的新改性物。
与结晶且不太生物活性形式相比,这种新形式的脱落酸可能需要较低的剂量、降低的喷雾施用率和施用次数。此外,制剂助剂如溶剂或表面活性剂作为除活性成分(“ai”)之外的其它化学品的比率随着高活性且同时更高负载的液体制剂而降低。针对稀释的水性制剂,还通过不需要杀生物剂和由于移动的体积较小而导致的物流成本较低来提供环境优势。
例如农业、兽医或医药上有用的化合物的新改性物(例如溶剂化物)的发现可以提供改进产品的表现特性的机会。它扩大了制剂科学家可用于设计例如具有靶向释放曲线或其它所需特性的化合物的剂型的材料库。当通过发现有用化合物的新的溶剂化结晶形式或无定形形式来扩大所述库时,显然是有利的。晶体的固态化学不能预测有机溶剂是否可以结合到晶体中。可能发生晶体溶剂化的方式也是不可预测的。不存在允许预测化合物是否将作为有机溶剂的溶剂化形式存在的规则。因此,具有新的溶剂化结晶形式或无定形形式的脱落酸及其有效制备方法将是有利的。
由于上述原因,仍然需要允许生产具有脱落酸的高负载液体制剂的替代方案,其中脱落酸完全溶解并保持其高生物活性。
出乎意料地,上述需求通过先前未知的脱落酸与特定的N-取代吡咯烷酮(优选N-正丁基吡咯烷酮(NBP))的溶剂化物以及包含脱落酸与特定的N-取代吡咯烷酮(优选N-正丁基吡咯烷酮(NBP))组合的组合物来满足。
因此,本发明提供脱落酸与式(I)的N-取代吡咯烷酮的溶剂化物,
其中R是含3至6个碳原子,更优选4至5个,特别是4个碳原子的线性或支化的饱和烷基,
其中式(I)的N-取代吡咯烷酮优选为N-正丁基吡咯烷酮(“NBP”)。
此外,本发明提供液体高负载直至过饱和的农业化学组合物,其包含,优选由以下组成:
a)基于所述组合物的总重量,10重量%至50重量%的脱落酸;和
b)基于所述组合物的总重量,0.1重量%至90重量%的一种或多种式(I)的N-取代吡咯烷酮,
其中R是含3至6个碳原子,更优选4至5个,特别是4个碳原子的线性或支化的饱和烷基,其优选是N-正丁基吡咯烷酮;
c)非必要地,基于所述组合物的总重量,至多50重量%的一种或多种共溶剂;和
d)非必要地,基于所述组合物的总重量,至多50重量%的一种或多种配制助剂,和
e)非必要地,基于所述组合物的总重量,至多50重量%的一种或多种附加的活性成分。
本发明进一步提供包含根据本发明的农业化学组合物和一种或多种溶剂的喷雾液体。
本发明的另一目的为根据本发明的溶剂化物和/或农业化学组合物或喷雾液体用于处理植物的用途。
本发明还提供调节植物生长和/或植物发育的方法,包括以下步骤:将根据本发明的溶剂化物和/或农业化学组合物或喷雾液体施用于植物。
本发明进一步公开了改进植物的应激耐受性或者引发或影响植物的生理过程操纵应激的方法,包括以下步骤:将根据本发明的溶剂化物和/或农业化学组合物或喷雾液体施用于植物。
此外,本发明还涵盖调节植物开花期的方法,包括以下步骤:将根据本发明的溶剂化物和/或农业化学组合物或喷雾液体施用于植物。
本发明进一步提供提高作物的产量和质量的方法,包括以下步骤:将本发明的溶剂化物和/或农业化学组合物或喷雾液体施用于作物。
本发明的另一个目的是如上定义的溶剂化物用于改进高载量液体脱落酸组合物的稳定性的用途。
此外,本文还公开了如上定义的本发明溶剂化物用于促进脱落酸与植物的相互作用的用途。
本发明进一步提供增强红色葡萄着色的方法,包括以下步骤:将本发明的溶剂化物、农业化学组合物或喷雾液体施用于植物。
进一步提供了本发明的溶剂化物、农业化学组合物或喷雾液体用于谷物的收获前处理以避免收获前发芽以及谷粒储存期间发芽的用途。
WO 2017/211572公开了N-取代的吡咯烷酮促进农业化学活性剂渗透的用途,其中将脱落酸列为农业化学活性剂的长列表中。然而,在所述文献中没有暗示具有脱落酸的溶剂化物和具有N-取代吡咯烷酮作为溶剂的脱落酸的高载量液体组合物,以及将活性成分稳定在作为溶剂化物的假多晶型状态(pseudopolymorphous state)。
本发明的溶剂化物有利地允许生产脱落酸的过饱和液体农业化学组合物,其中脱落酸完全溶解并保持其高生物活性。本发明的溶剂化物和组合物进一步导致活性成分的摄取增加。此外,本发明的溶剂化物和组合物不表现出植物毒性。它们是稳定的并且在喷雾液体中提供良好的溶解性能。本发明的组合物,特别是如果式(I)中的R是具有4个碳原子的烷基,例如正丁基,则进一步显示出有利的环境分布型(profiles)。
这些组合物提供以下令人意外的特征:
-具有NBP的制剂比除了具有NMP其它方面相同的制剂显著更稳定,
-通过添加去离子水直至超过脱落酸在溶剂/水混合物中的溶解度,使脱落酸从采用溶剂NMP或NBP的溶液中沉淀,采用NMP产生结晶固体沉淀物,而采用NBP的可比溶液显示液体无定形相沉淀。
-在采用NMP或NBP的脱落酸的简单溶液的溶剂蒸发后,采用NMP沉积物总是结晶的,并且最通常,采用NBP是无定形的。
本文所使用的术语“本发明的溶剂化物”、“溶剂化物”、“脱落酸溶剂化物”和类似术语表示溶剂分子与脱落酸配位。在这种情况下,溶剂是指式(I)的N-取代吡咯烷酮,特别是N-正丁基吡咯烷酮(NBP)。这些术语和类似术语在本发明中可以互换使用。
本发明的溶剂化物优选包含天然存在形式的(S)(+)-脱落酸。天然脱落酸具有以下式:
它的IUPAC名称为(2Z,4E)-5-[(1S)-1-羟基-2,6,6-三甲基-4-氧代环己-2-烯-1-基]-3-甲基戊-2,4-二烯酸。它是可商购的,例如从江西的New Reyphon BiochemicalCo.Technology Co.,Ltd.以及从Sichuan Lomon Bio Technology Co.,Ltd.。
除了脱落酸的天然形式之外,本发明还涵盖所有异构体,例如(R)-(-)-脱落酸对映异构体,以及异构体的混合物,例如(S)-(+)-和(R)-(-)-脱落酸的外消旋混合物。此外,本发明的各种实施方案中的脱落酸可以由合适的前体原位产生,例如脱落酸酯,例如脱落酸甲酯。
因此,溶剂化物可以是(S)-(+)-对映异构体的溶剂化物、(R)-(-)-对映异构体的溶剂化物、所述脱落酸对映异构体的外消旋体的溶剂化物、或所述对映异构体的任何混合物的溶剂化物,特别是脱落酸的任何前述形式的假多晶型状态(无定形溶剂化物)。溶剂化物作为假多晶型状态形式的分类可见于例如Hilfiker和von Raumer(eds,Polymorphismin the Pharmaceutical Industry,Wiley VCH,2019(第2页)和Polymorphism inPharmaceutical Solids/edited by Harry G.Brittain,第二版(Drugs and thePharmaceutical Sciences;v.192(第1-2页)。
在一个实施方案中,本发明的溶剂化物是无定形溶剂化物。
在一些实施方案中,溶剂化物是化学计量的1:1溶剂化物,但不能排除在还含有一种或多种制剂助剂如表面活性剂的液体制剂(参见下文)中也可以存在非化学计量通道类型(Hilfiker和von Raumer(编辑,Polymorphism in the Pharmaceutical Industry,Wiley VCH,2019)。
本文所使用的术语“1:1溶剂化物”或类似术语“单溶剂化物”表示具有脱落酸的溶剂化物对于每个脱落酸分子包含约一个溶剂分子。
在以下描述中,为本发明的溶剂化物提供差示扫描量热法(DSC)参数(例如去溶剂化峰、去溶剂化起始)。应当理解,除非另有说明,否则温度值的精度为+/-0.1℃。
在一些实施方案中,溶剂化物的特征在于平均约125℃(标准偏差9℃)的去溶剂化峰。
溶剂化物还可以通过热重分析(TGA)表征,其测量作为温度的函数的样品质量变化。TGA可用于量化在加热时从溶剂化物结构中除去溶剂时观察到的重量损失。总重量损失、去溶剂化的起始温度和重量损失曲线的形状提供了关于溶剂化物结构的信息。(Polymorphism:in the Pharmaceutical Industry,Hilfiker,R.,Wiley-VHC VerlagGmbH&Co.KGaA,Weinheim,2006pp 77)。
在一些实施方案中,溶剂化物的特征在于DTG-曲线(差示热成像分析)中在约180℃(标准偏差18℃)和262℃(标准偏差2℃)的平均转折点处的两个峰。
本发明的溶剂化物可以通过包括以下步骤的方法制备和离析:(i)将脱落酸溶解在式(I)的N-取代吡咯烷酮,优选N-正丁基吡咯烷酮中;和(ii)蒸发式(I)的N-取代吡咯烷酮,优选N-正丁基吡咯烷酮。
在所述方法中,必须选择避免本发明溶剂化物分解的蒸发条件,例如在工作实施例中所示。在一个实施方案中,在室温下蒸发过量的溶剂直至恒重。
另一种制备和离析脱落酸与式(I)的N-取代吡咯烷酮,优选N-正丁基吡咯烷酮的溶剂化物的方法包括以下步骤:(i)将脱落酸溶解在式(I)的N-取代吡咯烷酮,优选N-正丁基吡咯烷酮中;(ii)提供适合于沉淀脱落酸溶剂化物的条件;和(iii)离析所沉淀的溶剂化物。
制备脱落酸与式(I)的N-取代的吡咯烷酮(优选N-正丁基吡咯烷酮)的溶剂化物、本发明的农业化学组合物(如下所述)或本发明的喷雾液体(如下所述)的另一种方法包括以下步骤:(i)将脱落酸的前体分子,例如脱落酸酯,例如脱落酸甲酯溶解在式(I)的N-取代吡咯烷酮,优选N-正丁基吡咯烷酮中;和(ii)由所述前体分子原位产生脱落酸。
本发明的溶剂化物适用于生产脱落酸的高载量组合物。
根据本发明的农业化学组合物包含:
a)基于所述组合物的总重量,10重量%至50重量%,优选15重量%至40重量%,更优选25重量%至35重量%的脱落酸;和
b)基于所述组合物的总重量,0.1至90重量%,优选10至85重量%,更优选25至75重量%的一种或多种式(I)的N-取代吡咯烷酮,
其中R是含3至6个碳原子,更优选4至5个,特别是4个碳原子的线性或支化的饱和烷基,在一个尤其优选的实施方案中,所述N-取代吡咯烷酮是N-正丁基吡咯烷酮。
c)非必要地,基于所述组合物的总重量,至多50重量%,优选0或0.1至30重量%,更优选0或1至20重量%的一种或多种共溶剂;和
d)非必要地,基于所述组合物的总重量,至多50重量%,优选0.1至40重量%,更优选1至35重量%的一种或多种配制助剂,和
e)非必要地,基于所述组合物的总重量,至多50重量%,优选0或0.1至40重量%,更优选0或1%至30重量%的一种或多种另外的活性成分,包括脱落酸的其它衍生物,如葡萄糖酯或o-葡糖苷。
本发明的组合物优选包含天然存在形式的(S)-(+)-脱落酸。为了在商业农产品中使用,优选天然存在形式的脱落酸,归因于显著提高的生物活性。
除了脱落酸的天然形式之外,本发明的组合物可以包含所有异构体,例如(R)-(-)-脱落酸对映异构体,和异构体的混合物,例如(S)-(+)-和(R)-(-)-脱落酸的外消旋混合物,以及脱落酸与式(I)的N-取代吡咯烷酮,特别是N-丁基吡咯烷酮的多晶型状态、无定形状态和假多晶型状态(溶剂化物)。
优选地,在本发明的组合物中,脱落酸(呈上述任何异构体形式)作为本发明的溶剂化物存在。这也适用于本发明组合物的所有优选实施方案和施用形式,例如喷雾液体。
在一个优选的实施方案中,本发明的组合物不包含(0%)共溶剂(c)。
在另一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种共溶剂(c)。
共溶剂(如果存在的话)优选选自:脂族或芳族烃,例如矿物油、甲苯、二甲苯或萘衍生物;卤代脂族或芳族烃如二氯甲烷或氯苯,油,基于植物的油如玉米胚芽油或菜籽油;油衍生物,如菜籽油甲酯;二元醇或三元醇,如乙二醇、二乙二醇、丙二醇和甘油;聚二醇,如聚乙二醇、聚丙二醇和/或混合的聚亚烷基二醇(PAG);极性醚,如四氢呋喃(THF)或二烷;亚烷基二醇单烷基和二烷基醚,如丙二醇单甲基醚、丙二醇单乙基醚、乙二醇单甲基醚或单乙基醚;二甘醇二甲醚或四甘醇二甲醚;酰胺,如二甲基甲酰胺(DMF)、二甲基乙酰胺、二甲基辛酰胺、二甲基癸酰胺酮如丙酮;基于甘油和羧酸的酯,如甘油单乙酸酯、甘油二乙酸酯或甘油三乙酸酯;内酰胺;在酯结构部分中具有1至10个碳原子的链长度的乳酸酯;碳酸二酯;腈,例如乙腈、丙腈、丁腈或苄腈;亚砜和砜,如二甲亚砜(DMSO)和噻吩烷。更优选地,共溶剂选自酰胺,优选含5至20,优选6至15,更优选8至12个碳原子的羧酸的N,N-二烷基酰胺,更优选N,N-二甲基酰胺。最优选地,共溶剂是壬酰基二甲基酰胺。
在一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种配制助剂(d)。
在另一个优选的实施方案中,本发明的组合物不包含(0%)配制助剂(d)。
所用的配制助剂(d)可以是适于赋予本发明组合物或由这些组合物制备的使用形式特定性能(例如特定物理、技术和/或生物学性能)的那些物质(例如,即用型作物保护剂,例如喷雾液体或拌种产品)。通常,本发明的组合物或相应的喷雾液体可以含有通常用于配制目的的任何固体或液体配制助剂。
配制助剂d)优选选自酸化剂、助剂、分散剂、乳化剂、光降解稳定剂、自发性试剂(spontaneity agent)和润湿剂。更优选地,配制助剂选自至少一种分散剂和/或润湿剂和/或酸化剂。最优选地,农业化学组合物包含至少一种分散剂、至少一种润湿剂和至少一种酸化剂,其中分散剂、润湿剂和酸化剂可以是相同的化合物或不同的化合物。
分散剂定义为使液体和固体成分在整个农业化学组合物中均匀分布的化学添加剂。通过分散以及乳化也包括术语乳化剂的液体或固体成分,可以实现均匀分布。
分散剂和润湿剂的实例是聚丙烯酸的盐,木质素磺酸的盐,苯酚磺酸或萘磺酸的盐,环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺、与取代的酚(优选烷基酚或芳基酚)的缩聚物,磺基琥珀酸酯的盐,牛磺酸衍生物(优选牛磺酸烷基酯),聚乙氧基化醇或酚的磷酸酯,多元醇的脂肪酸酯,以及含有硫酸酯、磺酸酯和磷酸酯的化合物的衍生物,例如烷基芳基聚二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯、蛋白质水解产物、木质素亚硫酸盐废液和甲基纤维素。
酸化剂的实例是pH值低于脱落酸的无机酸和有机酸。优选地,酸化剂是含1至15个碳原子,更优选具有1至8个碳原子,最优选2至6个碳原子的羧酸。丙酸和乳酸是特别优选的酸化剂。
助剂的优选实例是例如,铺展剂,例如烷基硅氧烷,和/或盐,例如有机或无机铵或盐,例如硫酸铵或磷酸氢二铵,和/或保留促进剂和/或湿润剂,例如甘油,和/或渗透剂和/或粘着剂(促进粘着到植物表面的试剂),例如羧甲基纤维素和呈粉末、颗粒或胶乳形式的天然和合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂,例如脑磷脂和卵磷脂和合成磷脂,和/或功能性聚合物。
在本文中有用的渗透剂是通常用于改进农业化学活性物质向植物中渗透的所有那些物质。
在本文中,渗透剂通过其从(通常含水的)施用液体和/或从喷雾沉积物渗透到植物角质层中并因此增加活性成分在角质层中的移动性的能力来定义。文献中描述的方法(Baur等人,1997,Pesticide Science 51,131-152)可用于确定这种性能。实例包括醇烷氧基化物,例如椰子脂肪乙氧基化物(10)或异十三烷基乙氧基化物(12),脂肪酸烷基酯,例如菜籽油甲酯或大豆油甲酯,脂肪胺烷氧基化物,例如牛油胺乙氧基化物(15)或铵盐盐,例如硫酸铵或磷酸氢二铵,植物油,例如菜籽油、葵花油或矿物油,例如石蜡油。
有用的保留促进剂包括所有那些降低动态表面张力的物质,例如磺基琥珀酸二辛酯,或增加粘弹性的物质,例如羟丙基瓜尔胶聚合物。
可以存在于根据本发明的组合物中的有用的功能性聚合物是具有大于10 000的分子量的合成或天然来源的高分子量化合物。功能性聚合物可以用作例如抗漂移剂或增加耐雨性。
其它可能的配制助剂包括自发性促进剂。当活性成分和/或另外的配制助剂不溶于水并且当施用在水中进行时,自发促进剂(如支链醇乙氧基化物或丁基烷氧基化物或相关的表面活性剂)的存在是有利的。
另外的组分可以是稳定剂,例如冷稳定剂(防冻剂)、防腐剂、抗氧化剂、光稳定剂或改进化学和/或物理稳定性的其它试剂。可另外存在泡沫产生剂或消泡剂。
所使用的防腐剂可以是有机酸及其酯,例如抗坏血酸、抗坏血酸棕榈酸酯、山梨酸酯、苯甲酸、4-羟基苯甲酸甲酯和丙酯、丙酸酯、苯酚(例如2-苯基苯酚酯)、1,2-苯并异噻唑啉-3-酮、甲醛、亚硫酸及其盐。
合适的消泡剂是脂肪酸烷基酯烷氧基化物,有机聚硅氧烷如聚二甲基硅氧烷及其与微细、非必要硅烷化氧化硅的混合物;全氟烷基膦酸酯和全氟烷基次膦酸酯、石蜡、蜡和微晶蜡及其与硅烷化氧化硅的混合物。各种泡沫抑制剂的混合物也是有利的,例如硅油、石蜡油和/或蜡的混合物。
此外,组合物和由其衍生的使用形式非必要地包含作为配制助剂的香料、保护胶体、粘结剂、粘合剂、增稠剂、触变剂、多价螯合剂和/或络合剂。其它可能的配制助剂是矿物油和植物油。
在一个优选的实施方案中,本发明的组合物不包含(0%)附加的活性成分(e)。
在另一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种附加的活性成分(e)。
另外的活性成分(e)(如果存在的话)不同于脱落酸,并且优选为农业化学活性成分,包括脱落酸的其它衍生物,优选葡萄糖酯或o-葡糖苷。
它们优选选自农药、植物生长调节剂、植物营养素、驱避剂、安全剂和两种或更多种这些活性成分的组合。
除草剂和植物生长调节剂的实例包括:
乙草胺、苯并噻二唑、苯并噻二唑-S-甲酯、氟锁草醚、氟锁草醚钠、苯草醚、甲草胺、烯草胺、咯草酮、咯草酮钠、莠灭净、氨唑草酮、酰胺草胺、酰嘧磺隆、环吡草胺、环吡草胺钾、环吡草胺甲酯、氨草啶、杀草强、氨基磺酸铵、嘧啶醇、油酰草胺、磺草胺、莠去津、艾维甘氨酸、唑啶草酮、四唑磺隆、叠氮炔、氟丁酰胺、草除灵、草除灵乙酯、苯磺隆、氟草灵、苄呋胺酯、地散利、苄嘧磺隆、苄嘧磺隆-甲酯、灭草松、二苯唑草酮、双环磺隆、苯草酮、苯氟草、苯甲酰丙酸、苄腺嘌呤、氟吡草酮、治草醚、双丙硫磷、双丙硫磷钠、双嘧苯甲酸、双嘧苯甲酸钠、除草定、溴丁肽、溴非草酯、溴苯腈、溴嘧磺隆、丁胺磷、丁氧肟酮、丁草胺、氟丙嘧草酯、丁胺磷、丁烯草胺、仲丁灵、丁氧草酮、丁草酯、唑草酮、甲萘威、长酰草胺、唑酮草酯、唑酮草乙酯、香芹酮、氯化氯胆碱、甲氧除草醚、草灭平、氯唑禾草灵、氯唑禾草灵丁酯、氯溴隆、氯丁胺、氯芬酸、氯芬酸钠、虫螨灵、氯芴醇、氯芴醇甲酯、氯达敏、氯嘧磺隆、氯嘧磺隆乙酯、矮壮素、硝草醚、4-氯苯氧基乙酸、氯酞、氯苯胺灵、敌草快、绿麦隆、氯磺隆、吲哚酮、吲哚酮乙酯、环庚草醚、醚磺隆、烯草酮、炔草酯、炔草酯、四唑草酮、异恶草酮、氯甲禾草灵、氯禾草灵、二氯吡啶酸、氯酯磺草胺、氯酯磺草胺-甲酯、座果酸、异丙隆、氰胺、氰草津、环酰苯胺、环草酯、环丙嘧磺隆、噻草酮、环草隆、氰氟草酯、氰氟草酯丁酯、赛草快、环草津、赛普拉唑、细胞分裂素、2,4-D、2,4-DB、敌草隆/敌草隆、茅草枯、达胺齐特、达唑草、正癸醇、去苯敌草、去草净、对甲苯磺酰吡唑特(DTP)、敌草酯、敌草畏、麦草畏、敌草腈、禾草灵、精禾草灵、禾草灵、甲基禾草灵、精禾草灵、唑嘧磺草胺、敌草酯、乙基敌草酯、枯莠隆、敌草快、吡氟草胺、氟吡草隆、氟吡草隆钠、敌克酸钠、敌草隆、哌啶草酯、二甲草胺、异戊净、噻吩草胺、精噻吩草胺、敌草平、敌草隆、敌硝胺、地乐酚、敌草特、苯敌草胺、二异丙基萘、敌草快、敌草快、二溴敌草快、二噻草隆、敌草隆、DNOC、乙基乙嗪、敌草丹、EPTC、禾草威、丁氟灵、胺苯磺隆、胺苯磺隆-甲酯、萘乙酸乙酯、乙烯利、噻啶磺隆、噻嗪、乙呋草黄、乙氧禾草灵、乙氧禾草灵、乙氧苯磺隆、乙氧苯酰胺、F-5331,即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺、F-7967,即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮、唑禾草灵、精唑禾草灵、精唑禾草灵乙酯、精恶唑禾草灵乙酯、唑磺酮、四唑草胺、非草隆、麦草氟、氟禾草灵异丙酯、氟禾草灵甲酯、啶磺隆、双氟磺草胺、吡氟禾草灵、精吡氟禾草灵、丁吡氟禾草灵、精吡氟禾草灵、氟唑特、氟磺隆、氟磺隆钠、氟吡磺隆、氟草灵、氟噻草胺(噻氟酰胺)、氟芬吡、氟芬吡-乙基、氟美曲林、氟美舒仑、氟米草酸、氟米草酸-戊基、氟米沙嗪、氟米丙啶、氟米草隆、氟代芬、氟甘草醚、氟代甘草醚-乙基、氟哌酸、氟丙嘧啶、氟丙酸、氟嘧磺隆、氟吡嘧磺隆-甲基钠、氟虫醇、氟虫醇-丁基、氟利酮、氟氯啶酮、氟草烟、氟草烟-甲庚基、氟吡嘧啶、氟他酮、氟硫嘧啶、氟硫草胺、氟虫胺、氟虫脲、甲磺隆、氟虫脲、磷胺、呋虫胺、赤霉酸、草铵膦、草铵膦、草铵膦-P、草铵膦-P-铵、草铵膦-P-钠、草甘膦、草甘膦-异丙基铵、H-9201,即O-(2,4-二甲基-6-硝基苯基)O-乙基异丙基硫代磷酰胺酯、卤磺胺草醚、氯吡嘧磺隆、氯吡嘧磺隆-甲酯、吡氟氯禾灵、精吡氟氯禾灵、吡氟氯禾灵-乙氧基乙酯、精吡氟氯禾灵-乙氧基乙酯、吡氟氯禾灵-甲酯、精吡氟氯禾灵、六嗪酮、HW-02,即1-(二甲氧基磷酰基)乙基(2,4-二氯苯氧基)乙酸酯、咪草酯、咪草酯-甲酯、咪草啶酸、咪草啶酸-铵、甲基咪草烟、灭草烟、灭草烟-异丙基铵、灭草喹、灭草喹-铵、咪草烟、咪草烟-铵、咪唑磺隆、咪草非特、茚草芬、茚嗪氟草胺、吲哚乙酸(IAA)、4-吲哚-3-基丁酸(IBA),碘磺隆、碘磺隆甲基钠、碘磺隆、碘磺隆钠、碘苯腈、异丙卡巴宗、异脲、异丙磺隆、异丙隆、异丙隆、异恶草醚、异恶草胺、异唑草酮、异唑草酮、KUH-043,即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-唑、卡丁酯、酮螺环、乳多芬、环草定、利谷隆、马来酰肼、MCPA、MCPB、MCPB-甲基、-乙基和-钠、甲霜灵、甲霜灵钠、甲霜灵丁氧基、甲霜灵对丁氧基、甲霜灵对二甲基铵、甲霜灵对-2-乙基己基、甲霜灵对-钾、苯噻草胺、苯氟醚、甲哌啶、甲基二磺隆、甲基二磺隆-甲酯、甲基磺草酮、噻唑隆、威百亩、苯酰胺草酯、苯嗪草酮、吡草胺、苯唑磺隆、甲基吡嘧磺隆、甲噻唑啉、甲氧苯酮、甲基杀草隆、1-甲基环丙烯、异硫氰酸甲酯、异苯脲、异硫氰酸甲酯、甲基苯脲、甲氧溴隆、异丙甲草胺、S-异丙甲草胺、甲磺草胺、甲氧隆、嗪草酮、甲磺隆、甲磺隆-甲酯、禾草敌、单内酯、单脲、单脲硫酸二氢酯、单谷隆、单磺隆、单磺隆酯、灭草隆、MT-128,即6-氯-N-[(2E)-3-氯丙-2-烯-1-基]-5-甲基-N-苯基哒嗪-3-胺、MT-5950,即N-[3-氯-4-(1-甲基乙基)苯基]-2-甲基戊酰胺、NGGC-011,1-萘乙酸(NAA)、萘乙酰胺(NAAm)、2-萘氧基乙酸、萘丙胺、敌草胺、萘草胺、NC-310,即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑、草不隆、烟嘧磺隆、尼吡嘧啶、硝唑啉、硝基苯醚、硝基愈创木酚酯、硝基苯酚钠(异构体混合物)、硝基氟醚、壬酸(nonanoic acid)、去甲氟草醚、奥苯威、邻磺胺嘧啶、安磺灵、二唑、唑草酮、唑嘧啶、唑酮、氧氟草醚、多效唑、百草枯、百草枯二氯化物、壬酸(pelargonic acid)、二甲戊灵、戊唑醇、五氟磺草胺、戊草胺、戊恶唑酮、全氟啶酮、哌唑草胺、苯磺胺、苯甲地安、苯甲地安乙酯、毒莠定、吡啶甲萘芬、匹诺沙登、哌啶磷、吡虫啉、吡虫啉-丁基、氟虫草胺、扑灭磺隆、扑灭磺隆、甲基苯磺唑、丙氟唑、丙环嗪、丙二胺、普氟乐林、丙氧嘧啶、丙己二酮、丙己二酮-钙、羟茉莉酮原、扑灭通、扑草净、毒草胺、敌稗、喔草酯、扑灭津、苯胺灵、异丙草胺、丙苯磺隆、丙苯磺隆钠、丙吡嘧磺隆、丙草酰胺、丙硫灵、苄草丹、氟丙磺隆、丙草胺、双唑草腈、吡唑草醚、吡唑草醚-乙酯、吡唑磺草酮、吡唑酯(吡唑特),吡嘧磺隆、吡嘧磺隆-乙酯、吡唑氧芬、嘧菌酯、嘧菌酯-异丙酯、嘧菌酯-丙酯、嘧菌肟、吡菌酮、哒唑醇、哒螨酯、嘧菌灵、嘧菌胺、嘧菌胺、嘧菌胺、嘧菌胺钠、嘧磺隆、嘧磺草胺、二氯喹啉酸、喹草酸、喹诺拉明、喹禾灵、喹禾灵-乙酯、精喹禾灵、精喹禾灵、精喹禾灵-糠基、玉嘧磺隆、苯嘧磺草胺、仲丁草酮、稀禾定、双嘧隆、西玛嗪、西草净,SN-106279,即(2R)-2-({7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基}氧基)丙酸甲酯、磺草酮、磺胺草酯(CDEC)、甲磺草胺、嘧磺隆、甲嘧磺隆、草硫膦(草甘膦三甲铵)、磺嘧磺隆、SW-065、SYN-523、SYP-249,即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯、SYP-300,即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并恶嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮、特丁胺、丁噻隆、四萘嗪、特呋喃三酮、环丙三酮、对苯草酮、特草定、特丁威、特丁草胺、特丁通、特丁嗪、特丁炔、噻醚草胺、噻氟酰胺、噻唑氟隆、噻唑吡隆、噻二唑胺、噻苯隆、噻酮磺隆、噻酮磺隆-甲酯、噻吩磺隆、噻吩磺隆-甲酯、硫苄威、噻卡巴、苯吡唑草酮、肟草酮、氟唑草酯、醚苯磺隆、三嗪氟草胺、三唑草酰胺、苯磺隆、苯磺隆-甲酯、三丁磷、三氯乙酸(TCA)、绿草定、三氟嘧啶、三乙嗪、三氟嘧磺隆、三氟嘧磺隆钠、氟乐灵、氟胺磺隆、氟胺磺隆-甲酯、三甲磺隆、三氟磺隆、齐托夫、灭草猛、ZJ-0862,即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺,以及下列化合物:
植物生长调节剂优选是控制生理反应如生长、开花节律、细胞分裂和种子成熟的植物激素。植物生长调节剂的实例包括天然和合成植物激素,例如苄基腺嘌呤、辛酸、癸醇、吲哚乙酸、茉莉酸及其酯、水杨酸及其酯、抗倒酸及其酯,例如抗倒酸乙酯、烯效唑、烯效唑-P、赤霉酸、三十烷醇、激动素和油菜素甾醇。进一步优选的是脱落酸的衍生物,特别是葡萄糖酯以及脱落酸的o-葡糖苷。
杀真菌剂的实例包括:
(1)麦角甾醇生物合成抑制剂,例如涕灭灵、阿扎康唑、联苯三唑醇、糠菌唑、环丙唑醇、双氯曲唑、苯醚甲环唑、烯唑醇、精烯唑醇、十二烷吗啉、乙酸十二烷吗啉、氟环唑、依他康唑、氯苯嘧啶醇、腈苯唑、环酰菌胺、苯锈啶、丁苯吗啉、氟喹唑、氟嘧醇、氟硅唑、粉唑醇、呋唑醇、呋唑醇-顺、己唑醇、抑霉唑、硫酸抑霉唑、亚胺唑、种菌唑、叶康唑、腈菌唑、萘替芬、氟苯唑醇、唑醇、多效唑、稻瘟酯、戊菌唑、粉病灵、咪鲜胺、丙环唑、丙硫菌唑、嘧啶威、啶虫脒、喹康唑、西美康唑、螺环胺、戊唑醇、特比萘芬、丁康唑、三唑酮、三唑醇、三甲吗啉、曲氟咪唑、曲福林、曲替康唑、文康唑、伏立康唑、1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、1-(2,2-二甲基-2,3-二氢-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯、N'-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基亚氨基甲酰胺、N-乙基-N-甲基-N'-{2-甲基-5-(三氟甲基)-4-[3-(三甲基甲硅烷基)丙氧基]苯基}亚氨基甲酰胺和O-[1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基]1H-咪唑-1-硫代甲酸酯。
(2)呼吸抑制剂(呼吸链抑制剂),例如联苯吡菌胺、啶酰菌胺、萎锈灵、二氟林、呋菌胺、氟吡菌酰胺、氟酰胺、氟唑菌酰胺、呋吡菌胺、呋美菌酰胺、吡唑吡菌胺(顺式差向外消旋体1RS,4SR,9RS和反式差向外消旋体1RS,4SR,9SR的混合物)、吡唑吡菌胺(反式差向外消旋体)、吡唑吡菌胺(反式差向对映异构体1R,4S,9S)、吡唑吡菌胺(反式差向对映异构体1S,4R,9R)、吡唑吡菌胺(顺式差向外消旋体1RS,4SR,9RS)、吡唑吡菌胺(顺式差向对映异构体1R,4S,9R)、吡唑吡菌胺(顺式差向对映异构体1S,4R,9S)、灭锈胺、氧化萎锈灵、戊氟草醚、吡噻菌胺、氟唑菌胺、噻氟草胺、1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-(三氟甲基)-1H-吡唑-4-甲酰胺、3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺、3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺、N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、N-[9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺和N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺。
(3)作用于呼吸链的复合物III的呼吸抑制剂(呼吸链抑制剂),例如,嘧菌胺、氨磺隆、嘧菌酯、氰霜唑、对甲氧嘧菌酯、对氧菌酯、醚菌酯、烯菌酯、唑菌酮、咪唑菌酮、苯氧菌酯、氟嘧菌酯、醚菌酯、苯氧菌胺、肟菌胺、啶氧菌酯、唑菌胺酯、唑菌胺酯、嘧菌酯、吡菌威、氯啶菌酯、肟菌酯、(2E)-2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺、(2E)-2-(甲氧基亚氨基)-N-甲基-2-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)乙酰胺、(2E)-2-(甲氧基亚氨基)-N-甲基-2-{2-[(E)-({1-[3-(三氟甲基)苯基]乙氧基}亚氨基)甲基]苯基}乙酰胺、(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)乙叉基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(2E)-2-{2-[({[(2E,3E)-4-(2,6-二氯苯基)丁-3-烯-2-叉基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺、5-甲氧基-2-甲基-4-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)-2,4-二氢-3H-1,2,4-三唑-3-酮、(2E)-2-{2-[({环丙基[(4-甲氧基苯基)亚氨基]甲基}硫烷基)甲基]苯基}-3-甲氧基丙-2-烯酸甲酯、N-(3-乙基-3,5,5-三甲基环己基)-3-(甲酰氨基)-2-羟基苯甲酰胺、2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺和(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺。
(4)有丝分裂和细胞分裂抑制剂,例如苯菌灵、多菌灵、氯芬唑、乙霉威、噻唑菌胺、氟吡菌胺、麦穗宁、戊菌隆、噻菌灵、甲基托布津(thiophanate-methyl)、托布津(thiophanate)、苯酰菌胺、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶和3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪。
(5)具有多位点活性的化合物,例如波尔多液、敌菌丹、克菌丹、百菌清、铜制剂如氢氧化铜、环烷酸铜、氧化铜、氯氧化铜、硫酸铜、抑菌灵、二噻农、多果定、多果定游离碱、福美铁、氟灭菌丹、灭菌丹、双胍辛、双胍辛乙酸盐、双胍辛胺、双胍辛胺烷基苯磺酸盐、双胍辛胺三乙酸盐、代森锰铜、代森锰锌、代森锰、代森联、代森联锌、喔星铜、普罗帕脒、丙森锌、硫和硫制剂,例如多硫化钙、福美双、甲苯抑菌灵、代森锌和福美锌。
(6)电阻诱导剂,例如例如苯并苯-S-甲基、异噻菌胺、苯菌唑和噻菌胺。
(7)氨基酸和蛋白质生物合成抑制剂,例如安多普林,杀稻瘟菌素-S、嘧菌环胺、春雷霉素、水合盐酸春雷霉素、嘧菌胺、嘧霉胺和3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉。
(8)ATP产生抑制剂,例如三苯锡乙酸酯、三苯锡氯化物、三苯锡氢氧化物和硅噻菌胺。
(9)细胞壁合成抑制剂,例如苯噻菌胺、烯酰吗啉、氟吗啉、异丙菌胺、双炔酰菌胺、多抗霉素、多氧霉素、有效霉素A和缬草酸盐。
(10)脂质和膜合成抑制剂,例如联苯、灭草散、氯硝胺、克瘟散、土菌灵、碘威、异稻瘟净、稻瘟灵、霜霉威、霜霉威盐酸盐、丙硫威、定菌磷、五氯硝基苯、四氯硝基苯和甲基立枯磷。
(11)黑色素生物合成抑制剂,例如环丙酰胺、双氯氰菌胺、氰菌胺、四氯苯酞、咯喹酮、三环唑和{3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸2,2,2-三氟乙酯。
(12)核酸合成抑制剂,例如苯霜灵、苯霜灵-M(精苯霜灵)、磺嘧酚酯、氯唑菌酮、甲菌胺、乙菌胺、呋霜灵、恶霉灵、甲霜灵、精甲霜灵-M(精甲霜灵)、呋酰胺、恶霜灵和恶喹酸。
(13)信号转导抑制剂,例如乙菌利、拌种咯、咯菌腈、异菌脲、腐霉利、喹氧灵和乙烯菌核利。
(14)解偶联剂,例如乐杀螨、敌螨普、嘧菌腙、氟啶胺和消螨普。
(15)其它化合物,例如苯噻唑、倍他沙嗪、辣椒霉素、香芹酮、灭螨猛、吡咯酮(克拉非酮)、硫杂灵、环氟菌胺、霜脲氰、环丙磺酰胺、达唑美、敌草威、双氯酚、双氯甲嗪、苯敌快、苯敌快甲酯硫酸盐、二苯胺、ecomat、苯吡嗪、氟甲草胺、氟酰胺、氟磺酰胺、氟噻菌胺、乙膦铝、乙膦钙、乙膦钠、六氯苯、伊鲁马霉素、甲磺威、异硫氰酸甲酯、美曲芬、灭虫霉素、游霉素、二甲基二硫代氨基甲酸镍、硝酞异丙酯、辛噻酮、奥沙威、氧苯硫脲、五氯苯酚及其盐、苯醚菊酯、磷酸及其盐、丙霉威-亚膦酸盐、丙醇钠、丙喹嗪、嘧啶吗啉、(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、硝吡咯菌素、替布氟喹、叶枯酞胺、托尼芬、三唑沙、三酰胺、扎里酰胺、2-甲基丙酸(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬-7-基酯、1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-恶唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、1-(4-{4-[5-(2,6-二氟苯基)-4,5-二氢-1,2-唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、1H-咪唑-1-甲酸1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基酯、2,3,5,6-四氯-4-(甲磺酰基)吡啶、2,3-二丁基-6-氯噻吩并[2,3-d]嘧啶-4(3H)-酮、2,6-二甲基-1H,5H-[1,4]二噻吩并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5R)-5-苯基-4,5-二氢-1,2-恶唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮、2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5S)-5-苯基-4,5-二氢-1,2-唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮、2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-{4-[4-(5-苯基-4,5-二氢-1,2-唑-3-基)-1,3-噻唑-2-基]哌啶-1-基}乙酮、2-丁氧基-6-碘-3-丙基-4H-色烯-4-酮、2-氯-5-[2-氯-1-(2,6-二氟-4-甲氧基苯基)-4-甲基-1H-咪唑-5-基]吡啶、2-苯基苯酚及其盐、3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、3,4,5-三氯吡啶-2,6-二甲腈、3-[5-(4-氯苯基)-2,3-二甲基-1,2-唑烷-3-基]吡啶、3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、5-氨基-1,3,4-噻二唑-2-硫醇、5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼、5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、5-甲基-6-辛基[1,2,4]三唑[1,5-a]嘧啶-7-胺、(2Z)-3-氨基-2-氰基-3-苯基丙-2-烯酸乙酯、N'-(4-{[3-(4-氯苄基)-1,2,4-噻二唑-5-基]氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亚氨基甲酰胺、N-(4-氯苄基)-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、N-[(4-氯苯基)(氰基)甲基]-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、N-[(5-溴-3-氯吡啶-2-基)甲基]-2,4-二氯吡啶-3-甲酰胺、N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯吡啶-3-甲酰胺、N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2-氟-4-碘吡啶-3-甲酰胺、N-{(E)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、N'-{4-[(3-叔丁基-4-氰基-1,2-噻唑-5-基)氧基]-2-氯-5-甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-(1,2,3,4-四氢萘-1-基)-1,3-噻唑-4-甲酰胺、N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1R)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺、N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1S)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺、{6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸戊酯、吩嗪-1-甲酸、喹啉-8-醇、喹啉-8-醇硫酸酯(2:1)和叔丁基{6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯。
(16)其它化合物,例如1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、N-(4'-氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-(2',4'-二氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、3-(二氟甲基)-1-甲基-N-[4'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、N-(2',5'-二氟联苯-2-基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-甲酰胺、3-(二氟甲基)-1-甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺、5-氟-1,3-二甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺、2-氯-N-[4'-(丙-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺、3-(二氟甲基)-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺、N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、3-(二氟甲基)-N-(4'-乙炔基联苯-2-基)-1-甲基-1H-吡唑-4-甲酰胺、N-(4'-乙炔基联苯-2-基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、2-氯-N-(4'-乙炔基联苯-2-基)吡啶-3-甲酰胺、2-氯-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺、4-(二氟甲基)-2-甲基-N-[4'-(三氟甲基)联苯-2-基]-1,3-噻唑-5-甲酰胺、5-氟-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺、2-氯-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺、3-(二氟甲基)-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺、5-氟-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺、2-氯-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]吡啶-3-甲酰胺、(5-溴-2-甲氧基-4-甲基吡啶-3-基)(2,3,4-三甲氧基-6-甲基苯基)甲酮、N-[2-(4-{[3-(4-氯苯基)丙-2-炔-1-基]氧基}-3-甲氧基苯基)乙基]-N2-(甲基磺酰基)缬氨酰胺、4-氧代-4-[(2-苯基乙基)氨基]丁酸和{6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁-3-炔-1-基酯。
杀菌剂的实例包括以下:
溴硝丙二醇、双氯酚、三氯甲基吡啶、二甲基二硫代氨基甲酸镍、春雷霉素、辛噻酮、呋喃羧酸、土霉素、噻菌灵、链霉素、叶枯酞、硫酸铜及其它铜制剂。
杀虫剂、杀螨剂和杀线虫剂的实例包括以下:
(1)乙酰胆碱酯酶(AChE)抑制剂,例如氨基甲酸酯类,例如棉铃威、涕灭威、恶虫威、丙硫克百威、丁氧克百威、丁氧克百威、甲萘威、克百威、丁硫克百威、乙硫苯威、仲丁威、甲酸酯胺、呋线威、异丙威、灭虫威、灭多威、速灭威、杀线威、抗蚜威、残杀威、硫双威、噻虫酮、唑蚜威、混杀威、XMC和二甲苯威;或有机磷酸酯类,例如乙酰甲胺磷、甲基吡嗪磷、乙基谷硫磷、甲基谷硫磷、硫线磷、乙氧基氯乙氧磷、毒死蜱、甲基毒死蜱、蝇毒磷、杀螟磷、甲基内吸磷、二嗪农、敌敌畏/DDVP、百效磷、乐果、二甲基乙烯磷、二磺胺、EPN、乙硫磷、丙线磷、伐灭磷、克线磷、杀灭磷、杀灭硫磷、倍硫磷、噻唑磷、庚磷、咪唑磷、异杀灭磷、O-(甲氧基氨基硫代磷酰)水杨酸异丙酯、异硫磷、马拉硫磷、甲基苄胺磷、甲胺磷、杀扑磷、速灭磷、久效磷、敌乐磷、氧乐果、甲氧内吸磷、对硫磷、甲基对硫磷、稻瘟酯、甲拌磷、伏杀磷、亚胺硫磷、磷胺、辛硫磷、甲基嘧啶磷、丙溴磷、丙虫磷、丙硫磷、吡唑磷、哒螨硫磷、喹硫磷、噻虫胺磷、吡嘧硫磷、替美磷、特丁磷、杀虫畏、噻米通、三唑磷、三氯磷和伐米硫磷。
(2)GABA门控氯离子通道拮抗剂,例如环二烯-有机氯,例如氯丹和硫丹;或苯基吡唑类(fiproles),例如乙虫腈和氟虫腈。
(3)钠通道调节剂/电压门控钠通道阻断剂,例如拟除虫菊酯,例如丙烯酸酯、丙烯菊酯、d-顺式-反式丙烯菊酯、d-反式丙烯菊酯、联苯菊酯、生物丙烯菊酯、生物丙烯菊酯s-环戊烯基异构体、生物苄胺菊酯、环丙菊酯、氟氯氰菊酯、β-氟氯氰菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、γ-氯氟氰菊酯、氯氰菊酯、α-氯氰菊酯、β-氯氰菊酯、θ-氯氰菊酯、ζ-氯氰菊酯、氰苯菊酯[(1R)-反式异构体]、溴氰菊酯、氯菊酯[(EZ)-(1R)异构体]、高氰戊菊酯、醚菊酯、甲氰菊酯、氰戊菊酯、氟氰菊酯、氟菊酯、氟胺氰菊酯、氟醚菊酯、氟胺氰菊酯、氟醚菊酯、氟胺菊酯、氟醚菊酯、丙胺菊酯、炔菊酯、氯菊酯、苯醚菊酯[(1R)-反式异构体]、炔丙菊酯、除虫菊酯(除虫菊)、苄呋菊酯、氟硅菊酯、七氟菊酯、胺菊酯、胺菊酯[(1R)异构体]、四溴菊酯和四氟菊酯;或DDT;或甲氧滴滴涕。
(4)烟碱能乙酰胆碱受体(nAChR)激动剂,例如新烟碱类,例如啶虫脒、噻虫胺、呋虫胺、吡虫啉、烯啶虫胺、噻虫啉和噻虫嗪;或烟碱。
(5)烟碱能乙酰胆碱受体(nAChR)的变构活化剂,例如多杀菌素类,例如乙基多杀菌素和多杀菌素。
(6)氯离子通道活化剂,例如阿维菌素类/米尔倍霉素类,例如齐墩螨素、埃玛菌素苯甲酸盐、雷皮菌素和米尔螨素。
(7)保幼激素模拟物,例如保幼激素类似物,例如烯虫乙酯、烯虫炔酯和烯虫酯;或苯氧威;或吡丙醚。
(8)具有未知或非特异性作用机制的活性成分,例如烷基卤化物,例如甲基溴及其它烷基卤化物;或氯化苦;或硫酰氟;或硼砂;或吐酒石。
(9)选择性拒食剂,例如吡蚜酮;或氟啶虫酰胺。
(10)螨生长抑制剂,例如四螨嗪、噻螨酮和氟螨嗪;或特苯唑。
(11)昆虫肠膜的微生物破坏剂,例如苏云金芽孢杆菌以色列亚种、球形芽孢杆菌、苏云金芽孢杆菌aizawai亚种、苏云金芽孢杆菌kurstaki亚种、苏云金芽孢杆菌粉虫亚种和BT植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1。
(12)氧化磷酸化抑制剂、ATP破坏剂,例如丁醚隆;或有机锡化合物,例如三唑锡、三环锡和六苯丁锡氧;或克螨特;或四氯杀螨砜。
(13)中断H质子梯度的氧化磷酸化解偶联剂,例如虫螨腈、DNOC和氟虫胺。
(14)烟碱能乙酰胆碱受体拮抗剂,例如杀虫磺、杀螟丹盐酸盐、硫环素和硫磺唑钠。
(15)0型几丁质生物合成抑制剂,例如双三氟虫脲、定虫隆、除虫脲、氟螨脲、氟虫脲、氟铃脲、虱螨脲、双苯氟脲、多氟脲、伏虫隆和杀虫隆。
(16)1型几丁质生物合成抑制剂,例如噻嗪酮。
(17)蜕皮破坏剂,双翅目,例如灭蝇胺。
(18)蜕皮激素受体激动剂,例如环虫酰肼、特丁苯酰肼、甲氧苯酰肼和双苯酰肼。
(19)章鱼胺能激动剂(Octopaminergic agonist),例如双甲脒。
(20)复合物-III电子传递抑制剂,例如氟蚁腙;或灭螨醌;或嘧螨酯。
(21)复合物-I电子传递抑制剂,例如METI杀螨剂,例如喹螨醚、唑螨酯、嘧螨醚、哒螨灵、吡螨胺和唑虫酰胺;或鱼藤酮(鱼藤)。
(22)电压依赖性钠通道阻断剂,例如茚虫威;或氰氟虫胺。
(23)乙酰辅酶A羧化酶抑制剂,例如季酮酸和特特拉姆酸衍生物,例如螺螨酯、螺甲螨酯和螺虫乙酯。
(24)络合物-IV电子传递抑制剂,例如膦,例如磷化铝、磷化钙、膦和磷化锌;或氰化物。
(25)复合物-II电子传递抑制剂,例如腈吡螨酯。
(26)兰尼碱受体效应物,例如二酰胺类,例如氯虫苯甲酰胺和氟虫双酰胺。
具有未知作用机制的其它活性成分,例如胺氟草胺、印楝素、苯噻草、苯肟酯、联苯肼酯、溴丙酸酯、灭螨特、冰晶石、氰虫酰胺(Cyazypyr)、丁氟螨酯、三氯杀螨醇、氟螨嗪、氟噻虫砜、氟苯醚胺、氟虫腈、氟吡菌酰胺、呋喃虫酰肼、吡虫啉、异菌脲、哒螨达、吡氟喹宗和碘甲烷;以及另外的基于坚强芽孢杆菌(I-1582,Bioneem,Votivo)的制剂。
生物防治剂是本领域技术人员已知的,并且描述于例如"The Manual ofBiocontrol Agents,第5版,编者:Dr.Roma Gwynn,BCPC2014"中。
驱避剂的实例包括二乙基甲苯基酰胺、乙基己二醇和丁吡咯烷氧基。
植物营养素的实例包括用于向植物供应大量营养素和/或微量营养素的常规无机或有机肥料,例如含铵、钾或磷的肥料。
在一个实施方案中,本发明的组合物不包含(0%)其它配制助剂(d)或另外的活性成分(e)。
在另一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种配制助剂(d)和/或一种或多种附加的活性成分(e)。
在另一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种配制助剂(d)和没有附加的活性成分(e)。
在另一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种配制助剂(d)和/或一种或多种附加的活性成分(e)。
在另一个优选的实施方案中,本发明的组合物包含至少0.1重量%的一种或多种附加的活性成分(e)且没有配制助剂(d)。
本发明的组合物可以通过本领域技术人员已知的常规方法制备,例如混合组分a)、b)、非必要地,c)、d)和非必要地,e)。
根据本发明的喷雾液体包含上述农业化学组合物和一种或多种溶剂,优选水。其优选由本发明的组合物制备,优选通过用一种或多种溶剂稀释本发明的组合物。
优选地,所述喷雾液体包含0.001至20重量%,更优选0.002至1重量%,最优选0.005至0.2重量%的上述农业化学组合物,基于所述喷雾液体的重量。
在一个优选的实施方案中,喷雾液体包含:
a)0.0001至10重量%,优选0.0002至0.5重量%,最优选0.0005至0.1重量%的脱落酸,优选(S)-(+)-脱落酸,最优选(S)-(+)-脱落酸与N-丁基吡咯烷酮的溶剂化物。
b)0.0001重量%至10重量%,优选0.0002重量%至1.1重量%,最优选0.0005重量%至0.2重量%的一种或多种上面式(I)限定的N-取代吡咯烷酮;
c)非必要地,至多10重量%,优选0.0001至1重量%,更优选0.001至0.1重量%的一种或多种共溶剂;和
d)非必要地,至多10重量%,优选0.0001至1重量%,更优选0.001至0.1重量%的一种或多种配制助剂,和
e)非必要地,至多10重量%,优选0.0001至1重量%,更优选0.001至0.1重量%的一种或多种其它活性成分。
在本发明的一个优选的实施方案中,本发明的喷雾液体由a)至e)和溶剂组成,即,组分a)至e)和溶剂的百分比值合计为100%。
本发明的农业化学组合物和本发明的喷雾液体可用于处理处于其发育的任何阶段的植物。可以有利地用本发明的农业化学组合物或喷雾液体处理的示例性植物可以是谷物,包括小麦和水稻,C4植物玉米,甘蔗和高粱,烟草,咖啡,棉花,葡萄,柑橘类水果,苹果,西红柿,花生。所有更年期水果的水果,如苹果及其它仁果、桃及其它核果、鳄梨、香蕉、无花果、芒果、番木瓜、番茄和蔬菜,如卷心菜、葱属、胡椒、茄子、黄瓜及其它葫芦科、芦笋、大豆等。另一种用途是校正例如嗜球果伞素类或羧酰胺类杀真菌剂的绿化效果以促进成熟。
此外,本发明的农业化学组合物或喷雾液体可以用于例如调节植物生长和/或植物发育,改进植物的应激耐受性或启动或影响管理植物应激的生理过程,调节植物的开花期和改进产量和质量属性,如同化物含量或作物颜色。
本发明的农业化学组合物和本发明的喷雾液体还可用于处理种子以延缓种子萌发并避免玉米、大豆、高粱、甘蔗、油菜和春季谷物如大麦、小麦和黑麦的不利萌发。
此外,本发明的溶剂化物可用于促进脱落酸与植物的相互作用。
通过以下实施例进一步说明本发明,但本发明不限于以下实施例。
实施例:
除非另有明确说明,下文所述的百分比为重量百分比(重量%)。
所使用的原料是:
脱落酸(S)-(+)-脱落酸(纯度,90重量%),JiangXi New Reyphon BiochemicalCo.,LTD
Genagen NBP N-丁基吡咯烷酮溶剂,Clariant
Genagen PA壬酰基二甲基酰胺溶剂,Clariant
Emulsogen EL 360蓖麻油乙氧基化物分散剂/乳化剂,Clariant
Tivogen DR3401具有20%NBP分散剂/乳化剂的聚甘油酯,Clariant
Synergen 848正丁基EO/PO共聚物乳化剂/润湿剂,Clariant
mPEG ester脂肪酸mPEG酯/润湿剂,Clariant
丙酸丙酸酸化剂,Sigma Aldrich
Emulsogen MTP030植物脂肪醇烷氧基化物,乳化剂/分散剂/助剂,Clariant
Synergen KN助剂共混物,助剂,Clariant
LMF 1002农宝S-ABA 0.1%SL商用配方Sichuan Lomon Bio Technology CO.LTD
LMF 1009福施灌S-ABA 10%商用配方Sichuan Lomon Bio Technology CO.LTD
实施例1:脱落酸的物理状态与溶剂的关系
在这个试验中,在有和没有偏振光(POLAM)的显微镜中观察到脱落酸的物理状态与溶剂相关性的改变。
制备以下溶液1)至6):
溶液1:5%脱落酸的N-丁基吡咯烷酮溶液
溶液2:5%脱落酸的N-甲基吡咯烷酮溶液
溶液3:5%脱落酸的N-丁基吡咯烷酮/去离子水(9:1)溶液
溶液4:5%脱落酸的N-甲基吡咯烷酮/去离子水(9:1)溶液
溶液5:5%脱落酸的N-丁基吡咯烷酮/自来水(9:1)溶液
溶液6:5%脱落酸的N-甲基吡咯烷酮/自来水(9:1)溶液
在每种情况下,将1μL上述1)至6)的溶液施加在硅烷化玻璃上。使溶液在约25℃的室温和20-50%相对湿度下在载玻片上静置24小时,进行干燥。检查载玻片并在具有和不具有偏振光滤光器的情况下以400倍放大倍数拍摄液滴的原始边缘A)和中心B)的照片。结果示于图1(NMP)和图2(NBP)中。
发现活性化合物脱落酸从含有N-甲基吡咯烷酮的溶液(溶液2)4)6))中结晶(参见图1)并且不再以可用于从喷雾沉积物中摄取的形式存在,而含有N-丁基吡咯烷酮的溶液(溶液1)3)5))中的活性化合物脱落酸仍然以溶剂化形式存在(参见图2)。活性化合物脱落酸的这种溶剂化物有助于改进喷雾沉积物中的那些活性成分的溶解以及用于摄取到植物中的可用性。
实施例2:高载量脱落酸制剂的制备
表1中显示的脱落酸制剂A1至A7通过混合各种组分制备。然后将制剂在-10℃、40℃、25℃(室温)下储存八周,并在54℃下储存两周,以确定储存稳定性和相行为。
表1:脱落酸制剂(数字是基于制剂的重量%)
制剂A3与A4和A5与A6的比较显示,具有NBP的制剂比其它方面相同的具有NMP的制剂显著更稳定。
实施例3:渗透增强
在这个试验中,测量了脱落酸经过梨树叶的酶促离析角质层的渗透。所述方法的原理已经例如在WO-A-2005/194844或WO2017211572A1中进行了公开和详细描述。
为了确定渗透,将实施例中提及的组合物的10μl喷雾液施用于角质层的外侧。在所述喷雾液中,在每种情况下使用自来水。
在施用喷雾液后,在每种情况下使水蒸发,然后在每种情况下将腔室倒置并置于恒温槽中,将空气在限定的温度和湿度下吹到角质层的外部。因此,初始渗透在56%的相对湿度和10℃和25℃的设定温度下发生。通过高效液相色谱(HPLC)确定活性成分的渗透。
所述表显示,与ai本身相比,本发明的脱落酸制剂对活性成分的摄取强烈增加,并且与所试验的商业基准制剂相比增加。
由于经过表皮渗透的摄取对于生物活性是重要的,我们预期本发明组合物在本领域中具有优异的性能。
表2:在试验物质存在下脱落酸(喷雾液体中活性成分浓度为0.1g/L)的渗透
rH=空气湿度
实施例4:植物毒性
使用指示植物如一品红植物(例如梅洛品种(Merlot variety))检查脱落酸的植物相容性。如果在任何情况下都没有观察到坏死或其它植物毒性症状如叶子卷曲或变形,则认为所述物质是植物相容的并且没有植物毒性。
本发明的组合物在0.1g/L ai的相关使用浓度下没有显示植物毒性症状。所试验的参比物质(按1g/L的乙氧基化月桂醇)在一天内引起强烈的明显坏死。
实施例5:差示扫描量热法(DSC)
为了确定脱落酸的结晶形式的差异,对A)在N-丁基吡咯烷酮溶液中的40%脱落酸、B)在N-甲基吡咯烷酮溶液中的40%脱落酸、C)脱落酸的活性成分(90%纯度)的沉积物进行DSC。
对于沉积物,将40%脱落酸溶液干燥直至重量恒定。然后将样品用于试验吸附等温线。由于从3%-30%rh的重量没有变化,因此与脱落酸活性物(New Reyphon 90%/也取自吸附等温线实验)相比,将这些样品用于DSC测量。
表3:差示扫描量热法(DSC)
加热阶段一和加热阶段二的去溶剂化开始和峰值
此外,用相同的样品进行TGA。
实施例6:热重分析(TGA)
在NMP和NBP中长期干燥和蒸发脱落酸沉积物后,在TGA中观察到显著的分析差异。
脱落酸在NBP中的沉积物在DTG-曲线中显示出两个不同的峰,而脱落酸的沉积物仅显示出一个在约268℃的峰。脱落酸在NMP中的沉积物偶尔显示出在约262℃-268℃的峰之前的小的第二峰,这在所有三次测量中都是可见的。
表4:通过TG曲线表征的TGA数据
实施例7:在水溶液中沉淀
为了在水溶液中沉淀溶剂化物,通过在去离子水中以1:1和1:2的比例混合A)40%脱落酸在N-丁基吡咯烷酮中的溶液和B)40%脱落酸在N-甲基吡咯烷酮中的溶液来制备样品。为了分离沉淀,将样品离心短时间(min)。
在样品之间观察到显著的差异。尽管在40%脱落酸的N-甲基吡咯烷酮溶液中制备的样品强烈结晶,但具有40%脱落酸的N-丁基吡咯烷酮溶液的样品形成两个液相,当将水溶液冷却至5℃以及试图接种以引发结晶时,这两个液相甚至保持稳定。
Claims (22)
2.根据权利要求1所述的溶剂化物,其呈无定形状态。
3.根据权利要求1或2所述的溶剂化物,其中所述脱落酸是天然存在形式的(S)-(+)-脱落酸。
5.根据权利要求4所述的农业化学组合物,包含根据权利要求1至3中任一项所述的溶剂化物。
6.根据权利要求4或5所述的农业化学组合物,其中脱落酸是(S)-(+)-脱落酸。
7.根据权利要求4至6中任一项所述的农业化学组合物,其中式(I)的N-取代吡咯烷酮是N-正丁基吡咯烷酮。
8.根据权利要求4至7中任一项所述的农业化学组合物,包含:
a)基于所述组合物的总重量,10重量%至50重量%的脱落酸;和
b)基于所述组合物的总重量,0.1重量%至90重量%的一种或多种式(I)的N-取代吡咯烷酮,
其中R是含3至6个碳原子,更优选4至5个,特别是4个碳原子的线性或支化的饱和烷基,其中式(I)的N-取代吡咯烷酮优选为N-正丁基吡咯烷酮(NBP).
c)基于所述组合物的总重量,0重量%至50重量%的一种或多种共溶剂;和
d)基于所述组合物的总重量,0.1重量%至50重量%的一种或多种配制助剂;和
e)基于所述组合物的总重量,0重量%至50重量%的一种或多种另外的活性成分,包括脱落酸的其它衍生物,优选葡萄糖酯和/或o-葡糖苷。
9.根据权利要求4至8中任一项所述的农业化学组合物,其中组分d)的一种或多种配制助剂选自酸化剂、助剂、分散剂、乳化剂、光降解稳定剂、自发性试剂和润湿剂。
10.根据权利要求4至9中任一项所述的农业化学组合物,其中
a)基于所述组合物的总重量,脱落酸按10重量%至40重量%的量存在;
b)基于所述组合物的总重量,所述一种或多种N-取代吡咯烷酮按10重量%至90重量%的量存在;
c)基于所述组合物的总重量,所述一种或多种共溶剂按0重量%或0.1重量%至30重量%的量存在;和
d)基于所述组合物的总重量,所述另外的配制助剂按0.1重量%至35重量%的量存在;和
e)基于所述组合物的总重量,所述另外的附加活性化合物,包括脱落酸的其它衍生物,按0重量%或0.1重量%至30重量%的量存在。
11.喷雾液体制剂,包含根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物和一种或多种溶剂。
12.根据权利要求11所述的喷雾液体制剂,其中所述溶剂是水、甘油或任何基于植物油的液体载体。
13.根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体用于处理植物的用途。
14.调节植物生长和/或植物发育的方法,包括以下步骤:将根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体施用至植物。
15.改进植物的应激耐受性或者引发或影响植物的生理过程操纵应激的方法,包括以下步骤:将根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体施用至植物。
16.调节植物的开花期的方法,包括以下步骤:将根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体施用至植物。
17.改进作物的产量和质量的方法,包括以下步骤:将根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体施用至作物。
18.增强红色葡萄着色的方法,包括以下步骤:将根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体施用至植物。
19.根据权利要求1至3中任一项所述的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求12或13所述的喷雾液体用于谷物的收获前处理以避免收获前发芽以及谷粒储存期间发芽的用途。
20.一种或多种如权利要求1所限定的式(I)的N-取代吡咯烷酮用于改进液体脱落酸组合物的稳定性的用途。
21.一种或多种如权利要求1所限定的式(I)的N-取代吡咯烷酮用于促进脱落酸与植物相互作用的用途。
22.根据权利要求1至3中任一项所述的脱落酸的溶剂化物或根据权利要求4至10中任一项所述的农业化学组合物或根据权利要求11或12所述的喷雾液体的制备方法,包括以下步骤:(i)将脱落酸的前体分子,优选脱落酸酯,特别是脱落酸甲酯溶解在式(I)的N-取代吡咯烷酮,优选N-正丁基吡咯烷酮中;和(ii)由所述前体分子原位产生脱落酸。
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BR (1) | BR112022001732A2 (zh) |
CL (1) | CL2022000345A1 (zh) |
WO (1) | WO2021099079A1 (zh) |
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US4434180A (en) * | 1978-07-28 | 1984-02-28 | Visscher Saralee N | Insect control methods with abscisic acid |
EP0466353A1 (en) * | 1990-06-26 | 1992-01-15 | Toray Industries, Inc. | Composition for inhibiting flowering of plants and composition for prolonging duration of flowering of plants |
US5160528A (en) * | 1989-12-11 | 1992-11-03 | Isp Investments Inc. | Delivery system for agricultural chemicals |
US5389688A (en) * | 1989-12-11 | 1995-02-14 | Isp Investments Inc. | Water based microemulsion formulations |
CN109561676A (zh) * | 2016-06-08 | 2019-04-02 | 科莱恩国际有限公司 | N-取代的吡咯烷酮用于促进农用化学活性成分的渗透的用途 |
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US4209530A (en) | 1978-07-28 | 1980-06-24 | Endowment And Research Foundation At Montana State University | Insect control compositions employing abscisic acid |
JP3529793B2 (ja) | 1995-12-21 | 2004-05-24 | ナショナル リサーチ カウンシル オブ カナダ | Hyperabas:8’―メチル又は9’―メチル炭素原子に不飽和炭素置換基を有する生物学的に活性なアブシジン酸類似体 |
CL2008000243A1 (es) | 2007-01-31 | 2008-09-05 | Valent Biosciences Corp | Formulacion en granulos solubles de acido 2-cis,4-trans-(s)-abscisico; proceso de fabricacion; y metodo para mejorar la estabilidad al almacenamiento y la estabilidad fotoquimica. |
CA2731381C (en) | 2008-07-24 | 2016-08-23 | Valent Biosciences Corporation | Salts, aqueous liquid compositions containing salts of s-(+)-abscisic acid and methods of their preparation |
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2020
- 2020-10-28 CN CN202080068360.9A patent/CN114466836A/zh active Pending
- 2020-10-28 BR BR112022001732A patent/BR112022001732A2/pt unknown
- 2020-10-28 AU AU2020389474A patent/AU2020389474A1/en active Pending
- 2020-10-28 US US17/777,558 patent/US20220411370A1/en active Pending
- 2020-10-28 WO PCT/EP2020/080264 patent/WO2021099079A1/en unknown
- 2020-10-28 JP JP2022528260A patent/JP2023501721A/ja active Pending
- 2020-10-28 EP EP20797472.6A patent/EP4061798A1/en active Pending
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2022
- 2022-02-10 CL CL2022000345A patent/CL2022000345A1/es unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US4434180A (en) * | 1978-07-28 | 1984-02-28 | Visscher Saralee N | Insect control methods with abscisic acid |
US5160528A (en) * | 1989-12-11 | 1992-11-03 | Isp Investments Inc. | Delivery system for agricultural chemicals |
US5389688A (en) * | 1989-12-11 | 1995-02-14 | Isp Investments Inc. | Water based microemulsion formulations |
EP0466353A1 (en) * | 1990-06-26 | 1992-01-15 | Toray Industries, Inc. | Composition for inhibiting flowering of plants and composition for prolonging duration of flowering of plants |
CN109561676A (zh) * | 2016-06-08 | 2019-04-02 | 科莱恩国际有限公司 | N-取代的吡咯烷酮用于促进农用化学活性成分的渗透的用途 |
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BR112022001732A2 (pt) | 2022-08-16 |
JP2023501721A (ja) | 2023-01-18 |
WO2021099079A1 (en) | 2021-05-27 |
CL2022000345A1 (es) | 2022-10-28 |
AU2020389474A1 (en) | 2022-03-10 |
EP4061798A1 (en) | 2022-09-28 |
WO2021099079A9 (en) | 2021-08-12 |
US20220411370A1 (en) | 2022-12-29 |
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