CN101170903A - 含农药的聚合物水分散体的制备方法及其用途 - Google Patents
含农药的聚合物水分散体的制备方法及其用途 Download PDFInfo
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- CN101170903A CN101170903A CNA2006800159539A CN200680015953A CN101170903A CN 101170903 A CN101170903 A CN 101170903A CN A2006800159539 A CNA2006800159539 A CN A2006800159539A CN 200680015953 A CN200680015953 A CN 200680015953A CN 101170903 A CN101170903 A CN 101170903A
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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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/08—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 containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polymerisation Methods In General (AREA)
Abstract
本发明涉及一种通过水包油乳液的自由基聚合而制备包含农药且分散粒子的平均粒度为<1000nm的聚合物水分散体的方法,其中乳液的油相包含在至少一种烯属不饱和单体中的至少一种农药,该方法包括使至少一种农药在至少一种单体中的溶液在至少一种表面活性剂的存在下在水中乳化以得到平均液滴大小为<500nm的细乳液,和/或在乳化期间或随后加入至少一种农药,以及随后使细乳液在自由基条件下聚合。本发明还涉及因此得到的分散体在对抗有害微生物和/或用于调节植物生长和/或用于对抗不想要的植物生长和/或用于对抗不想要的昆虫或螨虫对植物的侵染和/或用于对抗植物病原性真菌和/或用于种子处理中的用途。
Description
本发明涉及一种通过水包油乳液的自由基聚合而制备包含农药且分散粒子的平均粒度为<1000nm的聚合物水分散体的方法,其中乳液的油相包含在至少一种烯属不饱和单体中的至少一种农药,以及涉及分散体在对抗有害微生物和/或用于调节植物生长和/或用于对抗不想要的植物生长和/或用于对抗不想要的昆虫或螨虫对植物的侵染和/或用于对抗植物病原性真菌和/或用于种子处理中的用途。
包含功能物质,尤其例如UV吸收剂或环氧树脂的聚合物水分散体由JP-A-7-292009已知。它们的制备方法包括将功能物质溶于不饱和单体中,使这种溶液在表面活性剂的存在下在水中乳化以得到平均粒度为5-500nm的单体乳液,使细乳液(miniemulsion)在自由基引发剂的存在下聚合。包含功能物质如UV吸收剂、环氧树脂、丙烯酸基聚合物、酚醛树脂、不饱和聚酯、酚基物质和石油树脂的水分散体用作粘合剂以及作为保护涂膜的添加剂。
WO 99/40123公开一种制备聚合物水分散体,包含均匀分布即分子分散的有机着色剂的聚合物分散粒子的方法。这种水分散体通过通过使包含溶解的有机着色剂的烯属不饱和单体,以水包油乳液的形式在自由基生成聚合引发剂的存在下聚合的细乳液聚合而制备,乳液的分散相基本包含直径为<500nm的含着色剂的单体液滴。在该发明的有利实施方案中,聚合中使用包含具有交联作用的单体的单体混合物。聚合物分散体对于沉降稳定。分散粒子的平均粒度为100-400nm。它们可使用常规干燥方法而从水分散体中分离。含着色剂的聚合物分散体例如用于高分子量有机和无机原料的着色,以及用于印墨和喷墨印刷油墨的着色。
EP-A-1 092 416公开了包含着色剂、荧光增白剂或UV吸收剂的细碎聚合物水分散体或可从中得到的粉状聚合物在化妆品组合物中作为着色组分的用途,聚合物基质包含均匀分布的着色剂、荧光增白剂或UV吸收剂。分散体优选根据由WO 99/40123已知的方法通过使包含溶解的着色剂、荧光增白剂或UV吸收剂的烯属不饱和单体细乳液聚合而制备。
额外的含着色剂的聚合物分散体由EP-A-1 191 041已知,其中含着色剂的聚合物粒子的平均粒度为小于1000nm。除有机着色剂外,UV吸收剂和荧光增白剂也适合用作着色剂。它们的制备方法包括将着色剂溶解在至少一种烯属不饱和单体中,使此溶液在水中乳化而形成常规粗乳液,使粗乳液均化而形成平均粒度小于1000nm的细乳液,以及使细乳液在自由基生成聚合引发剂、每种情况下根据所用的单体0.1-20重量%至少一种非离子表面活性化合物和1-50重量%至少一种两性聚合物的存在下聚合。聚合物粒子包含0.5-50重量%至少一种均匀分布的有机着色剂、荧光增白剂或UV吸收剂,均匀分布应理解为有机着色剂在聚合物基质中单分子溶解或以双分子或多分子聚集体的形式存在。
WO 01/10936公开了具有芯/壳结构的粒子,其中芯包含玻璃化转变温度Tg为小于40℃的聚合物和UV吸收剂,壳优选由来自丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯和/或甲基丙烯酸甲酯的聚合物组成。如果合适的话形成粒子的芯的聚合物可以交联。聚合物粒子通过乳液聚合而制备。包含UV吸收剂的聚合物粒子用于制备吸收UV辐射的聚合物组合物。
WO 2004/037867公开了包含烷基双烯酮的聚合物水分散体,其可通过使疏水性单烯属不饱和单体在烷基双烯酮的存在下细乳液聚合而得到。这些分散体用作纸的施胶剂以及作为皮革、天然和/或合成纤维和纺织品的疏水剂。
WO 2004/046234公开了包含至少一种UV吸收剂的细碎聚合物粉末在使聚合物对UV辐射作用稳定中的用途。聚合物粉末的聚合物粒子的粒度为500nm或更小。它们优选根据由上述文献WO 99/40123、EP-A 1 092 416和EP-A 1 191 041已知的方法通过细乳液聚合而制备。聚合物粒子包含0.5-50重量%至少一种在其中以分子或纳米结晶的形式均匀分布存在或在其中完全或仅部分涂有聚合物基质的UV吸收剂。
US 6 309 787公开了一种通过细乳液聚合而将着色剂包胶的方法,细乳液在表面活性剂、助表面活性剂和非离子表面活性剂的存在下制备。聚合后,得到由着色剂芯和聚合物壳形成的分散粒子。
DE-A 196 28 143公开了一种制备聚合物水分散体的方法。单体的聚合在随连续聚合将至少一部分含水单体细乳液连续引入聚合区的自由基含水细乳液聚合形式之后进行。
先前的申请10 2004 012 576.7公开了分散粒子平均粒度为<500nm,包含效应物质的聚合物水分散体,聚合物粒子包含由至少一种烯属不饱和单体作为芯而形成的聚合物基质,可溶于单体中的效应物质形成位于,至少部分位于芯表面上的粒子的聚合物基质。这些聚合物分散体的制备方法包括:首先使烯属不饱和单体在至少一种效应物质和一种表面活性剂的存在下在水中乳化,其中乳化粒子的平均粒度为<500nm,使它在至少一种自由基聚合引发剂的存在下首先在聚合区中仅使最多50%单体聚合而聚合,其中效应物质迁移到乳化粒子表面,使聚合仅在效应物质在产生的聚合物粒子表面大量或完全聚集后结束。这样可得到的分散体和从中通过挥发性组分蒸发而产生的聚合物粉末例如用于在化妆品或药物配制剂中,在表面涂层中,在纸、皮革或纺织品的生产中,在用于饲养动物的配制剂中使聚合物对于UV辐射、氧和/或热作用稳定。
在植物保护中,仅具有轻微水溶性的农药时常以水悬浮液或乳液的形式而配制。而乳液通常仍包含有机溶剂,悬浮液通常没有溶剂而配制。活性物质以粒度在μm范围内的细粒的形式存在于这些悬浮液中。
偶尔建议以含水微乳液的形式配制水不溶性杀真菌活性物质(例如见WO 02/082900、WO 02/45507和WO 99/65301)。与常规,通常分散相显示的液滴大小基本大于1μm的乳状-浑浊粗乳液相反,活性物质以液滴大小基本小于1000nm至10nm或更小的细碎形式存在于清澈至不透明微乳液中[关于这一点见D.J.Shaw,Introduction to Colloid and SurfaceChemistry,Butterworths,London,1986,第273页]。
先前的DE申请10 2004 020 332.6公开了一种具有至少一种在25℃和1013毫巴下在水中的溶解度不大于5g/l的杀真菌有机活性物质和平均粒度不大于300nm的细碎聚合物,聚合物粒子包含活性物质的含水活性物质组合物。聚合物由每种情况下根据单体的总量,至少60重量%至少一种在25℃下在水中的溶解度不大于30g/l的中性单烯属不饱和单体和至多40重量%至少一种其他烯属不饱和单体形成。这种活性物质组合物可通过使包含至少一种杀真菌活性物质和如果合适的话一种杀虫活性物质的烯属不饱和单体的水包油乳液自由基水乳液聚合而得到。然而,水分散体的稳定性仍需要改善。
本发明的目的是可得到一种制备在各自应用中以可控方式释放农业化学活性物质的包含农业化学活性物质的聚合物水分散体的方法,或者可使它们以对于迁移稳定或保护它们免于分解的形式得到。
该目的根据本发明用一种通过水包油乳液自由基聚合而制备分散粒子平均粒度为<1000nm的含农药的聚合物水分散体的方法而实现,其中乳液的油相包含在至少一种烯属不饱和单体中的至少一种活性物质,如果至少一种农药在至少一种单体中的溶液在至少一种表面活性剂的存在下在水中乳化,则得到平均液滴大小为<500nm的细乳液,和/或在乳化期间或随后加入至少一种农药,随后在自有基条件下使细乳液聚合。
这里给出的细碎聚合物的粒度为重均粒度,例如可通过动态光散射测定。用于此的方法为本领域技术人员所熟知的,例如来自H.Wiese inD.Distler,Wssrige Polymerdispersionen[Aqueous polymer dispersions],Wiley-VCH,1999,第4.2.1章,第40页及随后各页和其中引用的文献,以及H.Auweter and D.Horn,J.Colloid Interf.Sci.,105(1985),399,D.Lilge and D.Horn,Colloid Polym.Sci.,269(1991),704,或H.Wiese andD.Horn,J.Chem.Phys.,94(1991),6429。平均粒度优选10-250nm,尤其是20-200nm,特别优选30-150nm,非常特别优选30-100nm。
农药为本领域技术人员从文献中已知的。术语“农药”在这里意指至少一种选自杀虫剂、杀真菌剂、除草剂、生长调节剂和安全剂的活性物质(见Pesticide Manual,第13版(2003))。
用作活性物质的农药优选在水中的溶解度通常不大于5g/l,优选不大于3g/l的低水溶性的有机农药。下列杀虫剂说明了可能的活性物质,但应不限于这些:
·有机(硫代)磷酸酯类,例如高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(methamidophos)、杀扑磷(methidathion)、甲基一六零五(methyl parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、砜吸磷(oxydematon-methyl)、对氧磷(paraoxon)、一六零五(parathion)、稻丰散(phenthoate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙硫磷(prothiofos)、乙丙硫磷(sulprophos)、三唑磷(triazophos)或敌百虫(trichlorfon);
·氨基甲酸酯类,例如棉铃威(alanycarb)、丙硫克百威(benfuracarb)、虫威(bendiocarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、双氧威(fenoxycarb)、呋线威(furathiocarb)、二唑虫(indoxacarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)或唑蚜威(triazamate);
·合成除虫菊酯类,例如丙烯菊酯(allethrin)、氟氯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)和α、β、θ、ζ异构体、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(ethofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、(RS)氯氟氰菊酯(cyhalothrin)、氯氟氰菊酯(lambda-cyhalothrin)、咪炔菊酯(imoprothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊(pyrethrin)I、除虫菊II、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)或四氟菊酯(transfluthrin);
·节肢动物生长调节剂,例如a)几丁质合成抑制剂如苯甲酰脲类,如定虫隆(chlorfluazuron)、灭蝇胺(cyromacin)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(nufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯唑(etoxazole)或四螨嗪(clofentazine);b)蜕皮激素拮抗剂,如特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)或双苯酰肼(tebufenozide);c)保幼激素类似物,如蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)或双氧威(fenoxycarb);d)类脂生物合成抑制剂,如螺螨酯(spirodiclofen);
·新烟碱类(neonicotinoids),例如氟啶虫酰胺(flonicamid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、吡虫清(acetamiprid)或噻虫啉(thiacloprid);
·吡唑(pryazole)杀虫剂,例如acetoprole、乙虫清(ethiprole)、氟虫腈(fipronil)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)和氟吡唑虫(vaniliprole);
·此外,齐墩螨素(abamectin)、灭螨醌(acequinocyl)、虫螨脒(amitraz)、艾扎丁(azadirachtin)、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟唑虫清(chlorfenapyr)、杀虫脒(chlordimeform)、灭蝇胺(cyromazine)、杀螨硫隆(diafenthiuron)、茂醚(diofenolan)、埃玛菌素(emamectin)、硫丹(endosulfan)、喹螨醚(fenazaquin)、伐虫脒(formetanate)、伐虫脒盐酸盐(formetanate hydrochloride)、灭蚁腙(hydramethylnon)、增效醚(piperonyl butoxide)、哒螨酮(pyridaben)、拒嗪酮(pymetrozine)、艾克敌105(spinosad)、噻虫嗪(thiamethoxam)、硫环杀(thiocyclam)、啶虫丙醚(pyridalyl)、氟啶虫酰胺(flonicamid)、嘧螨酯(fluacrypyrim)、米尔螨素(milbemectin)、螺甲螨酯(spiromesifen)、吡氟硫磷(flupyrazofos)、NC 512、唑虫酰胺(tolfenpyrad)、氟虫酰胺(flubendiamide)、双三氟虫脲(bistrifluron)、benclothiaz、pyrafluprole、pyriprole、磺胺蜻酯(amidoflumet)、啼虫胺(flufenerim)、cyflumetofen、灭螨醌(acequinocyl)、lepimectin、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin)、氨基腙(amidrazone)、metaflumizone、N-乙基-2,2-二氯-1-甲基-环丙烷羧酰胺2-(2,6-二氯-α,α,α-三氟对甲苯基)腙、N-乙基-2,2-二甲基丙酰胺2-(2,6-二氯-α,α,α-三氟对甲苯基)腙,以及下式化合物:
下式的氨基异噻唑:
其中
R=-CH2OCH3或H,和
R’=-CF2CF2CF3;
下式的邻氨基苯甲酰胺:
以及下式的杀虫活性化合物:
下列杀真菌剂显示可能的活性物质但不限于这些:
·酰基丙氨酸类,例如苯霜灵(benalaxyl)、呋霜灵(furalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)或霜灵(oxadixyl);
·胺衍生物,例如4-十二烷基-2,6-二甲基吗啉(aldimorph)、多果定(dodine)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)、螺茂胺(spiroxamine)或克啉菌(tridemorph);
·苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinil);
·抗菌素,例如放线菌酮(cycloheximide)、灰黄霉素(griseofulvin)、春雷素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)、链霉素(streptomycin)或井冈霉素(validamycin A);
·唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、氰霜唑(cyazofamid)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(dinitroconazole)、氧唑菌(epoxiconazole)、氯唑灵(etridazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、麦穗宁(fuberidazole)、己唑醇(hexaconazole)、土菌消(hymexazole)、烯菌灵(imizalil)、酰胺唑(imibenconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、perfuazorate、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、涕必灵(thiabendazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizole)、戊叉唑菌(triticonazole)、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、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮或3-(3-溴-6-氟-2-甲基吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酸二甲基酰胺;
·二羧酰亚胺类,如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)或烯菌酮(vinclozolin);
·杂环化合物,如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、二噻农(dithianon)、乙菌定(ethirimol)、甲菌定(dimethirimol)、唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异嘧菌醇(fenarimol)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、异噻菌酮(octhilinone)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamide)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine)、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶或磺嘧菌灵(bupirimate);
·硝基苯基衍生物,如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)或异丙消(nitrophthal-isopropyl);
·苯基吡咯类,如拌种咯(fenpiclonil)或氟菌(fludioxonil);
·有机磷化合物,例如克瘟散(edifenphos)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、甲基立枯磷(tolclofos-methly)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、或亚磷酸;
·其他杀真菌剂,例如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、哒菌清(diclomezine)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、噻唑菌胺(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenone)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(tolclofos-methyl)、五氯硝基苯(quintozene)、苯酰菌胺(zoxamide)、稻瘟灵(isoprothiolane)、异稻瘟净(iprobenfos)、fluopicolide(氟吡菌胺(picobenzamid))、双炔酰菌胺(mandipropamid)、N-(2-{4-[3-(4-氯苯基)丙-2-炔基氧基]-3-甲氧基苯基}乙基)-2-甲基磺酰氨基-3-甲基丁酰胺、N-(2-{4-[3-(4-氯苯基)丙-2-炔基氧基]-3-甲氧基苯基}乙基)-2-乙基磺酰氨基-3-甲基丁酰胺、呋吡唑灵(furametpyr)、溴氟唑菌(thifluzamide)、吡噻菌胺(penthiopyrad)、环酰菌胺(fenhexamid)、3,4-二氯异噻唑-5-羧酸(2-氰基苯基)酰胺、flubenthiavalicarb、3-(4-氯苯基)-3-(2-异丙氧羰基氨基-3-甲基丁酰氨基)丙酸甲酯、{2-氯-5-[1-(6-甲基吡啶-2-基甲氧亚氨基)乙基]苄基}氨基甲酸甲酯、{2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基}氨基甲酸甲酯或磺菌胺(flusulfamide),
·下式的酰胺:
其中
X为CHF2或CH3,和
R1和R2相互独立地为卤素、甲基或卤代甲基;
·嗜球果伞素类(strobilurins),如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)或肟菌酯(trifloxystrobin);
·次磺酸衍生物,如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)或对甲抑菌灵(tolylfluanid);
·肉桂酰胺及类似物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph);
·酰胺杀真菌剂,如cyclofenamid或(Z)-N-[α-(环丙基甲氧亚氨基)-2,3-二氟-6-(二氟甲氧基)苄基]-2-苯基乙酰胺。
下列除草剂显示可能的活性物质但不限于这些:
抑制类脂生物合成的化合物,例如炔禾灵(Chlorazifop)、炔草酯(Clodinafop)、氯丁草(Clofop)、氰氟草酯(Cyhalofop)、氯甲草(diclofop)、唑禾草灵(Fenoxaprop)、高唑禾草灵(Fenoxaprop-p)、噻唑禾草灵(Fenthiaprop)、吡氟禾草灵(Fluazifop)、精吡氟禾草灵(Fluazifop-P)、吡氟氯禾灵(Haloxyfop)、精吡氟氯禾灵(Haloxyfop-P)、恶草醚(Isoxapyrifop)、唑酰草胺(Metamifop)、喔草酯(Propaquizafop)、喹禾灵(Quizalofop)、精喹禾灵(Quizalofop-P)、三氟苯氧丙酸(Trifop)、枯杀达(alloxydim)、丁氧环酮(Butroxydim)、烯草酮(clethodim)、环己烯草酮(cloproxydim)、噻草酮(Cycloxydim)、环苯草酮(Profoxydim)、稀禾定(Sethoxydim)、醌肟草(Tepraloxydim)、肟草酮(Tralkoxydim)、苏达灭(Butylate)、草灭特(Cycloat)、燕麦敌(Di-auate)、哌草丹(Dimepiperate)、扑草灭(EPTC)、禾草畏(Esprocarb)、抑草威(Ethiolate)、氮草(Isopolinate)、甲硫苯威(Methiobencarb)、草达灭(Molinate)、坪草丹(Orbencarb)、克草猛(Pebulate)、苄草丹(Prosulfocarb)、草克死(Sulfallat)、杀草丹(Thiobencarb)、丁草威(Tiocarbazil)、野麦畏(Tri-allate)、灭草猛(Vernolate)、呋草黄(Benfuresate)、乙呋草黄(Ethofumesate)和地散磷(Bensulide);
ALS抑制剂,如磺氨黄隆(Amidosulfuron)、四唑黄隆(Azimsulfuron)、苄嘧黄隆(Bensulfuron)、氯嘧黄隆(Chlorimuron)、绿黄隆(Chlorsulfuron)、醚黄隆(Cinosulfuron)、环丙黄隆(Cyclosulfamuron)、胺苯黄隆(Ethametsulfuron)、乙氧嘧黄隆(Ethoxysulfuron)、啶嘧黄隆(Fiazasulfuron)、氟定黄隆(Flupyrsulfuron)、甲酰氨磺隆(Foramsulfuron)、吡氯黄隆(Halosulfuron)、啶咪黄隆(Imazosulfuron)、碘黄隆(Iodosulfuron)、甲基二磺隆(Mesosulfuron)、甲黄隆(Metsulfuron)、烟嘧黄隆(Nicosulfuron)、环丙氧黄隆(Oxasulfuron)、氟嘧黄隆(Primisulfuron)、氟丙黄隆(Prosulfuron)、吡嘧黄隆(Pyrazosulfuron)、玉嘧黄隆(Rimsulfuron)、嘧黄隆(Sulfometuron)、乙黄黄隆(Sulfosulfuron)、噻黄隆(Thifensulfuron)、醚苯黄隆(Triasulfuron)、苯黄隆(Tribenuron)、三氟啶磺隆(Trifloxysulfuron)、氟胺磺隆(Triflusulfuron)、三氟甲磺隆(Tritosulfuron)、咪草酯(Imazamethabenz)、咪草啶酸(Imazamox)、甲基咪草烟(Imazapic)、灭草烟(Imazapyr)、灭草喹(Imazaquin)、咪草烟(Imazethapyr)、氯酯磺草胺(Cloransulam)、唑嘧磺胺(Diclosulam)、双氟磺草胺(Florasulam)、氟唑啶草(Flumetsulam)、唑草磺胺(Metosulam)、五氟磺草胺(Penoxsulam)、双嘧苯甲酸(Bispyribac)、肟啶草(Pyriminobac)、丙苯磺隆(Propoxycarbazone)、氟酮磺隆(Flucarbazone)、嘧苯草肟(Pyribenzoxim)、环酯草醚(Pyriftalid)和嘧硫苯甲酸(Pyrithiobac);
抑制光合成化合物,如莠去通(Atraton)、莠去津(Atrazine)、莠灭净(Ametryn)、叠氮津(Aziprotryn)、草净津(Cyanazine)、硫草净津(Cyanatryn)、可乐津(Chlorazine)、环草津(Cyprazine)、敌草净(Desmetryn)、戊草津(Dimethametryn)、杀草净(Dipropetryn)、草止津(Eglinazine)、抑草津(Ipazine)、麦苏百津(Mesoprazine)、醚草通(Methometon)、盖草津(Methoprotryne)、环氰津(Procyazine)、丙草止津(Proglinazine)、扑灭通(Prometon)、扑草净(Prometryn)、扑灭津(Propazine)、另丁津(Sebuthylazine)、密草通(Secbumeton)、西玛津(Simazine)、西玛通(Simeton)、西草净(Simetryn)、甲氧去草净(Terbumeton)、特丁津(Terbuthylazine)和去草净(Terbutryn);
原卟啉原IX氧化酶抑制剂,如氟锁草醚(Acifluorfen)、治草醚(Bifenox)、氯硝醚(Chlomethoxyfen)、草枯醚(Chlornitrofen)、氯氟草醚(Ethoxyfen)、消草醚(Fluorodifen)、乙羧氟草醚(Fluoroglycofen)、氯草醚(Fluoronitrofen)、氟黄胺草醚(Fomesafen)、氟呋草醚(Furyloxyfen)、氟硝磺酰胺(Halosafen)、乳氟禾草灵(Lactofen)、除草醚(Nitrofen)、硝氟草醚(Nitrofluorfen)、乙氧氟草醚(Oxyfluorfen)、异丙吡草酯(Fluazolate)、氟唑草酯(Pyraflufen)、吲哚酮草酯(Cinidon-ethyl)、酰亚胺苯氧乙酸(Flumiclorac)、氟嗪酮(Flumioxazin)、炔草胺(Flumipropyn)、达草氟(Fluthiacet)、噻二唑胺(Thidiazimin)、恶草灵(Oxadiazon)、炔丙唑草(Oxadiargyl)、唑啶炔草(Azafenidin)、氟酮唑草(Carfentrazone)、磺胺草唑(Sulfentrazone)、戊唑草(Pentoxazone)、双苯嘧草酮(Benzfendizone)、氟丙嘧草酯(Butafenacil)、双唑草腈(Pyraclonil)、氟唑草胺(Profluazol)、氟哒嗪草酯(Flufenpyr)、Flupropacil、吡氯草胺(Nipyraclofen)和乙胺草醚(Etnipromid);
除草剂,如氟哒草(Metflurazon)、达草灭(Norflurazon)、氟苯啶草(Flufenican)、吡氟草胺(Diflufenican)、氟吡酰草胺(Picolinafen)、氟丁酰草胺(Beflubutamid)、氟草同(Fluridone)、氟咯草酮(Flurochloridone)、呋草酮(Flurtamone)、甲基磺草酮(Mesotrione)、磺草酮(Sulcotrione)、异恶氯草酮(Isoxachlortole)、异氟草(Isoxaflutole)、吡草酮(Benzofenap)、吡唑特(Pyrazolynate)、苄草唑(Pyrazoxyfen)、苯并双环酮(Benzobicyclon)、杀草强(Amitrole)、异恶草酮(Clomazone)、苯草醚(Aclonifen)、4-(3-三氟甲基苯氧基)-2-(4-三氟甲基苯基)嘧啶以及下式的4-杂环基取代的苯甲酰基衍生物(参看WO-A-96/26202、WO-A-97/41116、WO-A-97/41117和WO-A-97/41118):
其中取代基R8-R13具有如下含义:
R8、R10代表氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基或C1-C6烷基磺酰基;
R9代表选自如下基团的杂环基:噻唑-2-基、噻唑-4-基、噻唑-5-基、异唑-3-基、异唑-4-基、异唑-5-基、4,5-二氢异唑-3-基、4,5-二氢异唑-4-基和4,5-二氢异唑-5-基,其中上述基团可带有一个或多个取代基,例如可由卤素、C1-C4-烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或C1-C4烷硫基单、二、三或四取代;
R11代表氢、卤素或C1-C6烷基;
R12代表C1-C6烷基;
R13代表氢或C1-C6烷基。
另外适合的除草剂为EPSP合酶抑制剂,例如草甘膦(glyphosate);
谷氨酰胺合酶抑制剂,例如草铵膦(Glufosinate)和双丙氨酰膦(bilanafos);
DHP合酶抑制剂,例如黄草灵(asulam);
有丝分裂抑制剂,如氟草胺(benfluralin)、地乐胺(butralin)、敌乐胺(dinitramine)、丁氟消草(ethalfluralin)、氟消草(fluchloralin)、异乐灵(isopropalin)、氟烯硝草(methalpropalin)、磺乐灵(nitralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)、卡乐施(profluralin)、氟乐灵(trifluralin)、甲基胺草磷(amiprofos-methyl)、草胺磷(butamifos)、氟硫草定(dithiopyr)、噻氟啶草(thiazopyr)、拿草特(propyzamide)、牧草胺(tebutam)、敌草索(chlorthal)、长杀草(carbetamide)、氯草灵(chlorbufam)、氯苯胺灵(chlorpropham)和苯胺灵(propham);
VLCFA抑制剂,如乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、丁烯草胺(butenachlor)、敌草乐(delachlor)、安塔(diethatyl)、克草胺(dimethachlor)、噻吩草胺(dimethenamid)、精噻吩草胺(dimethenamid-P)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、丙草胺(pretilachlor)、毒草胺(propachlor)、异丙草胺(propisochlor)、广草胺(prynachlor)、猛杀草(terbuchlor)、噻醚草胺(thenylchlor)、二甲苯草胺(xylachlor)、草毒死(allidochlor)、草立死(CDEA)、磺唑草(epronaz)、草乃敌(diphenamid)、草萘胺(napropamide)、萘丙胺(naproanilide)、烯草胺(pethoxamid)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、四唑酰草胺(fentrazamide)、莎稗磷(anilofos)、哌草磷(piperophos)、唑草胺(cafenstrole)、茚草酮(indanofan)和灭草环(tridiphane);
纤维素生物合成抑制剂,如敌草腈(dichlobenil)、草克乐(chlorthiamid)、异恶草胺(isoxaben)和胺草唑(flupoxam);
除草剂,如消草酯(dinofenate)、硝丙酚(dinoprop)、戊硝酚(dinosam)、地乐酚(dinoseb)、地乐消酚(dinoterb)、二硝甲酚(DNOC)、硝草酚(etinofen)和丁硝酚(medinoterb);
植物生长素除草剂,例如稗草胺(clomeprop)、2,4滴(2,4-D)、2,4,5-T、2甲4氯(MCPA)、酚硫杀(MCPA-thioethyl)、2,4-滴丙酸(dichlorprop)、高2,4-滴丙酸(dichlorprop-P)、2甲4氯丙酸(mecoprop)、高2甲4氯丙酸盐(mecoprop-P)、2,4-滴丁酸(2,4-DB)、2甲4氯丁酸(MCPB)、草灭平(chloramben)、麦草畏(dicamba)、草芽平(2,3,6-TBA)、麦草畏(tricamba)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、二氯皮考啉酸(clopyralid)、氟草烟(fluroxypyr)、毒莠定(picloram)、定草酯(triclopyr)和草除灵(benazolin);
植物生长素输送抑制剂,例如抑草生(naptalam)和二氟吡隆(diflufenzopyr);
另外还有:新燕灵(benzoylprop)、氟燕灵(flamprop)、麦草伏(flamprop-M)、溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、环庚草醚(cinmethylin)、苯丙隆(methyldymron)、乙苯酰草(etobenzanid)、膦铵素(fosamine)、威百亩(metam)、稗草畏(pyributicarb)、氯嗪草(oxaziclomefone)、棉隆(dazomet)、苯氧丙胺津(triaziflam)和甲基溴(methylbromide)。
术语“安全剂”具有如下含义:已知在某些情况下较好的除草耐受性可通过具有特异作用的除草剂与自身可发挥除草作用的有机活性化合物的结合应用而实现。由于它们降低或避开了对有用植物的损害,在这些情况下,这些化合物充当解毒剂或拮抗剂,称作“安全剂”。
下列显示了可能的安全剂,但应不限于这些:
解草酮(benoxacor)、喹氧乙酸(cloquintocet)、抑害腈(cyometrinil)、抑害胺(dichlormid)、dicyclonon、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯恶唑酸(isoxadifen)、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalic anhydride)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-唑烷(R-29148)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(AD-67;MON 4660)和解草腈(oxabetrinil)。
下列具有生长调节作用的化合物显示了可能的活性物质,但应不限于这些:
1-萘乙酰胺、1-萘乙酸、2-萘氧乙酸、调果酸(3-CPA)、促生灵(4-CPA)、嘧啶醇(ancymidol)、蒽醌、苄胺基嘌呤(BAP)、脱叶亚磷(butifos)、丁硫亚磷(tribufos)、地乐胺(butralin)、氯甲丹(chlorflurenol)、矮壮素(chlormequat)、苯哒酮酸(clofencet)、环丙酸酰胺(cyclanilide)、丁酰肼(daminozide)、麦草畏(dicamba)、双古钠(dikegulac-sodium)、噻节因(dimethipin)、杀螨醇(chlorfenethol)、硅长素(etacelasil)、乙烯利(ethephon)、果宝素(ethychlozate)、2,4,5-涕丙酸(fenoprop)、2,4,5-TP、氟磺胺素(fluoridamid)、调嘧醇(flurprimidol)、粉唑醇(flutriafol)、赤霉酸(gibberellicacid)、赤酶素(gibberellin)、双胍盐(guazatine)、烯菌灵(imazalil)、吲哚丁酸(indolylbutyric acid)、吲哚乙酸(indolylacetic acid)、karetazan、动力精(kinetin)、3,6-二氯-2-甲氧基苯甲酸1-(乙氧羰基)乙基酯(lactidichlor-ethyl)、抑芽丹(maleic hydrazide)、氟草磺(mefluidide)、甲哌(mepiquatchloride)、抑草生(naptalam)、多效唑(paclobutrazol)、调环酸(prohexadione-calcium)、喹草酸(quinmerac)、杀雄啉(sintofen)、调环烯(tetcyclacis)、赛二唑素(thidiazuron)、三碘苯甲酸、抑芽唑(triapenthenol)、triazethan、丁硫亚磷(tribufos)、抗倒酯(trinexapac-ethyl)和烯效唑(uniconazole)。
使烯属不饱和单体在油溶性着色剂的存在下的细乳液聚合例如从现有技术引用的WO-A-99/40123中已知。这种聚合方法和单体的详情尤其参考WO-A-99/40123的第3页第30行至第38页第6行和第69页第11行至第84页第43行。将该WO申请的这部分作为参考在此构成本发明的公开内容部分。其中所描述的用于制备细乳液的烯属不饱和单体、助剂和工艺措施以相同的方式应用于本发明方法中,不同之处在于使用常规用于对抗有害微生物,调节植物生长,对抗不想要的植物生长,对抗不想要的昆虫或螨虫对植物的侵染,对抗植物病原性真菌和/或种子处理以便保护不受微生物侵染和损害的本发明活性物质。
细乳液的油相例如包含根据所用单体的总量,0.5-60重量%,优选10-40重量%,尤其是10-30重量%至少一种活性物质。
适合的烯属不饱和单体例如为:
(a)50-100重量%至少一种在25℃和1013毫巴下在水中的溶解度为>0.01g/l的烯属不饱和单体A,
(b)0-50重量%至少一种在25℃和1013毫巴下在水中的溶解度为<0.01g/l的烯属不饱和单体B,和
(c)0-30重量%至少一种具有至少两个双键的烯属不饱和单体C。
这些单体或单体的组合详细描述于WO-A-99/40123中。事实上,来自组(a)-(c)的各个单体纯粹通过举例作为来自组(a)的单体应提到苯乙烯、α-甲基苯乙烯、乙酸乙烯酯、丙酸乙烯酯、马来酸二甲基酯、马来酸二乙基酯、烯属不饱和C3-C5羧酸的酯和具有1-6个碳原子的一价醇,以及乙酸烯丙基酯。
单体(a)还包含具有提高的水溶性,即在25℃和1013毫巴下>60g/l的那些单体A’。单体A’用来改性聚合物并通常在聚合物基质的合成中以0.1-20重量%,优选0.5-10重量%的量包含。这些单体的实例为丙烯酸、甲基丙烯酸、苯乙烯磺酸、2-丙烯酰氨基-2-甲基丙烷磺酸和乙烯基膦酸,以及阳离子源性(cationogenic)单体,例如丙烯酸二甲基氨基乙基酯、二甲基氨基丙基-甲基丙烯酰胺、二甲基氨基丙基丙烯酰胺或1-乙烯基咪唑,以及N-乙烯基甲酰胺、丙烯腈、甲基丙烯腈、丙烯酰胺、甲基丙烯酰胺和N-乙烯基吡咯烷酮。碱性单体以游离碱的形式、作为盐或以季铵化的形式用于聚合中。具有酸基团的单体可以以游离酸或以用碱金属碱或铵碱部分或完全中和的形式用于聚合中。
适合的来自组(b)的单体的实例为2-和4-甲基苯乙烯、对(叔丁基)苯乙烯、烯属不饱和C3-C5羧酸和分子中具有多于12个碳原子的醇的酯、月桂酸乙烯酯、硬脂酸乙烯酯和大分子单体,例如低聚丙烯酸丙烯酯。
来自组(c)的单体的实例为二丙烯酸二醇酯、丙烯酸烯丙基酯、甲基丙烯酸烯丙基酯、三丙烯酸三羟甲基丙烷、三甲基丙烯酸三羟甲基丙烷、三丙烯酸季戊四醇酯、四丙烯酸季戊四醇酯、二丙烯酸丁二醇酯、二乙烯基苯、二乙烯基脲和亚甲基双丙烯酰胺。
因此,为制备聚合物分散粒子,使用如下单体的组合:
(a)甲基丙烯酸甲酯、苯乙烯、乙酸乙烯酯、丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸、甲基丙烯酸、丙烯酰胺、甲基丙烯酰胺、丙烯腈和/或甲基丙烯腈,
(b)如果合适的话,丙烯酸月桂基酯、丙烯酸棕榈基酯和/或丙烯酸硬脂基酯,和
(c)如果合适的话,二丙烯酸丁二醇酯、丙烯酸烯丙基酯、甲基丙烯酸烯丙基酯、二乙烯基苯、三丙烯酸三羟甲基丙烷、三丙烯酸季戊四醇酯和/或四丙烯酸季戊四醇酯。
在本发明方法中,优选使用至少一种来自组(a)、(b)和(c)的单体。优选适于制备聚合物基质的另外的单体组合由如下单体的组合组成:
(a)甲基丙烯酸甲酯、甲基丙烯酸乙酯和/或丙烯酸,和
(c)二丙烯酸丁二醇酯、四丙烯酸季戊四醇酯、三丙烯酸季戊四醇酯、三丙烯酸三羟甲基丙烷、甲基丙烯酸烯丙基酯和/或丙烯酸烯丙基酯。
根据本发明方法,包含至少一种活性物质且聚合物分散粒子的平均粒度为<1000nm的聚合物水分散体通过使烯属不饱和单体细乳液聚合而得到。就这点而言,程序优选为这样的:首先将至少一种活性物质溶于至少一种单体中。在大多数情况下,活性物质单分子溶解;然而,它们也可以胶态分散体的形式溶解存在。然后将包含活性物质的单体溶液在至少一种表面活性剂的存在下在水中乳化。代替或除了表面活性剂外也可使用不溶于水的微粒或纳米粒子和/或作为乳液的稳定剂的单体(皮克林(pickering)效应)。这种稳定剂例如为纳米二氧化硅、氧化铝和硫酸镁。得到乳化液滴的平均液滴大小为<500nm的细乳液。
乳化根据WO-A-99/40123,第26页第11行至第32页第4行所详细描述的方法进行。例如对于乳化,使用各类型的高压均化器或使超声作用于作为基本组分包含至少一种优选溶于至少一种单体中的活性物质和水的粗乳液,参看EP-A-0 765 896、EP-A-1 008 380。在大多数情况下,混合物在表面活性剂的存在下乳化。然而,也可将活性物质加入细乳液中或在细乳液的制备期间加入。然而,如上所述,它们优选首先溶于至少一种单体中,以及以溶解的形式或以溶解的胶态分散体的形式在水中乳化。
用于制备细乳液的水相由水组成并如果合适的话包含将有机相乳液中形成的细碎单体液滴稳定在水相中的表面活性剂。表面活性剂例如以至多15重量%,例如0.05至15重量%,优选0.05-5重量%,尤其是0.1-2重量%的量使用,每种情况下根据整个分散体。它发现于水相、有机相或两相中。优选在乳化前将它加入水相中。原则上可使用所有表面活性剂。优选使用的表面活性剂为阴离子化合物和平均摩尔质量Mw为1000-100 000的两亲性共聚物。适合的表面活性剂的实例为月桂基硫酸钠、十二烷基硫酸钠、十六烷基硫酸钠、二辛基磺基琥珀酸钠和/或15-50摩尔氧化乙烯和/或氧化丙烯与1摩尔C12-C22醇的加成物。
另外,细乳液也可使用如果合适的话所用的两亲性聚合物稳定。如果使用两亲性聚合物,则它们以例如根据聚合中所用的单体,0.05-15重量%,优选0.5-5重量%的量使用。两亲性聚合物的实例为包含如下单体单元的共聚物:
(a)疏水性单烯属不饱和单体和
(b)单烯属不饱和羧酸、单烯属不饱和磺酸、单烯属不饱和膦酸或它们的混合物和/或碱性单体。
适合的疏水性单烯属不饱和单体为:
(a)例如苯乙烯、甲基苯乙烯、乙基苯乙烯、丙烯腈、甲基丙烯腈、C2-C18烯烃、单烯属不饱和C3-C5羧酸与一价醇的酯、乙烯基烷基醚、乙烯基酯或它们的混合物。从这组单体中,优选使用异丁烯、二异丁烯、苯乙烯和丙烯酸酯,例如丙烯酸乙酯、丙烯酸异丙基酯、丙烯酸正丁基酯和丙烯酸仲丁基酯。
两亲性共聚物包含如下单体作为亲水性单体:
(b)优选丙烯酸、甲基丙烯酸、马来酸、马来酸酐、衣康酸、乙烯基磺酸、2-丙烯酰氨基甲基丙烷磺酸、3-丙烯酰氨基丙烷磺酸、丙烯酸3-磺基丙基酯、甲基丙烯酸3-磺基丙基酯、苯乙烯磺酸、乙烯基膦酸或它们以共聚形式的混合物。酸单体可以以游离酸的形式或以部分或完全中和的形式存在。
另外适合的亲水性单体为碱性单体。它们可以单独或还以与上述酸性单体的混合物与疏水性单体(a)聚合。如果使用碱性和酸性单体的混合物,则取决于每次共聚的酸性与碱性单体的摩尔比,产生带阴离子或阳离子电荷的两性共聚物。
碱性单体例如为二(C1-C2)烷基氨基(C2-C4)烷基(甲基)丙烯酸酯或二烯丙基二甲基氯化铵。碱性单体可以以游离碱的形式、与有机或无机酸的盐的形式或用烷基卤季铵化的形式存在。碱性单体变成阳离子性的盐的形成或季铵化可部分或完全进行。这些化合物的实例为二甲基氨基乙基甲基丙烯酸酯、二乙基氨基乙基甲基丙烯酸酯、二甲基氨基乙基丙烯酸酯、二乙基氨基乙基丙烯酸酯、二甲基氨基丙基甲基丙烯酸酯、二甲基氨基丙基丙烯酸酯、二乙基氨基丙基甲基丙烯酸酯、二乙基氨基丙基丙烯酸酯和/或二甲基氨基乙基丙烯酰胺、二甲基氨基乙基甲基丙烯酰胺、二甲基氨基丙基丙烯酰胺、二甲基氨基丙基甲基丙烯酰胺和/或二烯丙基二甲基氯化铵。
如果游离酸形式的两亲性共聚物不充分溶于水,则它们以水溶性盐的形式使用,例如使用相应的碱金属、碱土金属和铵盐。这些盐例如通过用碱部分或完全中和两亲性共聚物的游离酸基而制备,碱例如氢氧化钠溶液、氢氧化钾溶液、氧化镁、氨或胺如三乙醇胺、乙醇胺、吗啉、三乙胺或丁胺用于中和。两亲性共聚物的酸基优选用氨或氢氧化钾溶液中和。另一方面,碱性单体或包含这种共聚单体的共聚物在水中的溶解度可通过用无机酸如盐酸或硫酸部分或完全中和,或通过加入有机酸如乙酸或对甲苯磺酸而提高。两亲性共聚物的摩尔质量例如为1000-100 000,优选1500-10 000。两亲性共聚物的酸值例如为50-500,优选150-350mgKOH/g聚合物。
特别优选包含如下单体共聚的那些两亲性共聚物:
(a)95-45重量%异丁烯、二异丁烯、苯乙烯或它们的混合物,和
(b)5-55重量%丙烯酸、甲基丙烯酸、马来酸、马来酸半酯或它们的混合物。
作为细乳液的稳定剂,特别优选使用包含如下单体共聚的共聚物:
(a)45-80重量%苯乙烯,
(b)55-20重量%丙烯酸和如果合适的话,
(c)以及另外的单体。
如果合适的话,共聚物可包含作为另外的单体(c)的共聚的马来酸半酯单元。这种共聚物例如可通过制备苯乙烯、二异丁烯或异丁烯或它们的混合物与马来酸酐在没有水存在下的共聚物,随后通过每摩尔共聚物中的酐基团使用5-50摩尔%一价醇使共聚物与醇反应而得到。适合的醇例如为甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇和叔丁醇。然而,也可使共聚物的酐基团与多价醇如二醇或丙三醇反应。然而,就这点而言,反应进行的程度仅使得多价醇的仅一个OH基团与酐基团反应。如果共聚物的酐基团不完全与醇反应,则未与醇反应的酐基团通过加入水而开环。
其他适合作为细乳液稳定剂的化合物例如为市售的单烯属不饱和酸的聚合物和N-乙烯基甲酰胺在聚亚烷基二醇上的接枝聚合物,例如如WO-A-96/34903所述。如果合适的话,至多10%的接枝的乙烯基甲酰胺单元可水解。接枝的乙烯基甲酰胺单元的比例优选根据聚亚烷基二醇,20-40重量%。优选使用摩尔质量为2000-10 000的聚乙二醇。
另外,两性离子聚亚烷基多胺和两性离子聚乙烯亚胺适合于稳定细乳液。这种化合物例如从EP-B-0 112 592中已知。它们例如可通过首先例如用氧化乙烯、氧化丙烯和/或氧化丁烯将聚亚烷基多胺或聚乙烯亚胺烷氧基化,随后例如用甲基溴或硫酸二甲酯将烷氧基化产物季铵化,然后用氯磺酸或三氧化硫将季铵化的烷氧基化产物硫酸化而得到。两性离子聚亚烷基多胺的摩尔质量例如为1000-9000,优选1500-7500。两性离子聚乙烯亚胺的摩尔质量优选1500-7500道尔顿。如果合适的话,除表面活性剂外,使用其他上述稳定剂用于稳定细乳液。如果使用它们,则它们以根据单体,0.05-15重量%,优选0.5-5重量%的量使用。
为了稳定细乳液,如果合适的话,在制备这些乳液中额外使用不可聚合的疏水性化合物,例如烃(例如脂族或芳族烃(如十六烷)),具有10-24个碳原子的醇,摩尔质量Mw<100 000的疏水性聚合物,四烷基硅烷和/或上述化合物的混合物。这种稳定剂的实例为十六烷,十氢化萘,橄榄油,平均摩尔质量Mw为500-50 000的聚苯乙烯,摩尔质量Mw为500-5000的硅氧烷、聚(丙烯酸正丁酯)如AcronalA 150 F或PnBA(丙烯酸正丁酯(120℃在异丙醇中)的高压温度溶液聚合物,在25℃下在异丙醇中测定的K值为24),平均摩尔质量Mw为100-10 000的乙烯、丙烯、1-丁烯、2-丁烯、1-戊烯或1-己烯的均聚物,平均摩尔质量为100-10 000的至少两种上述烯烃的共聚物和/或平均摩尔质量Mw为至少100,优选400-10 000的聚异丁烯,鲸蜡醇,硬脂醇,棕榈醇和/或山萮醇。另外可能的疏水性不可聚合的化合物为成膜助剂或增塑剂,例如来自BASF的Plastilit3060(C4-C6二羧酸的二(正丁基)酯的工业混合物),此外还有树脂如松香基树脂(参看Ullmanns Encycl.Techn.Chem.,第4版(1976),第12卷,第525-538页)和烃类树脂(参看Encycl.Polym.Sci.Eng.,(1987)第7卷,第758-782页),例如来自Hercules的Cristalex F 85。例如提到Foral85 E,来自Hercules的高度氢化松香基树脂的甘油酯(软化点:86℃)。任选使用疏水性不可聚合的化合物。它们在25℃和1巴下在水中的溶解度为<0.1g/l。如果使用它们,则它们以根据聚合中所用的单体,1-10重量%,优选2-6重量%的量使用。
K值为类似于DIN 5372测定的相对粘度值。它包含纯溶剂的流动速率相对于在相同溶剂中0.1重量%聚合物溶液的流动速率(也参看Cellulosechemie,第13卷(1932),第58-64页,和Kirk-Othmer Encyclopediaof Chemical Technology,第23卷,第967-968页)。K值为聚合物平均分子量的测量尺度。就这点而言,高K值对应于高平均分子量。
为了得到稳定的聚合物水分散体,如果合适的话可额外在保护胶体的存在下进行聚合。它们的平均摩尔质量Mw通常大于500,优选大于1000。保护胶体的实例为聚乙烯醇,纤维素衍生物如羧基甲基纤维素,聚乙烯吡咯烷酮,聚乙二醇,乙酸乙烯酯和/或丙酸乙烯酯在聚乙二醇上的接枝聚合物,一端或两端用烷基、羧基或氨基封端的聚乙二醇,聚二烯丙基二甲基氯化铵和/或多糖,尤其例如水溶性淀粉、淀粉衍生物和蛋白质。这种产物例如描述于Rmpp,Chemie Lexikon,第9版,第5卷,第3569页或E.Husemann和R.Werner的Houben-Weyl,Methoden der organischenChemie,第4版,第14/2卷,第IV章,Umwandlung von Cellulose und Strke[Conversion of Cellulose and Starch],第862-915页,以及Ullmann’sEncyclopedia of Industrial Chemistry,第6版,第28卷,第533页及随后各页,Polysaccharides中。
适合的例如为所有类型淀粉,例如直链淀粉和支链淀粉,天然淀粉,疏水或亲水改性淀粉,阴离子淀粉,阳离子改性淀粉,降解淀粉,例如可氧化、热、水解或酶催进行分解的淀粉,和能够用于淀粉分解的天然和改性淀粉。另外适合的保护胶体为在水中可溶胀的糊精和交联的水溶性淀粉。
作为保护胶体,优选使用可例如通过淀粉分解而转化成水溶形式的天然水溶性淀粉,以及阴离子改性淀粉如氧化马铃薯淀粉。特别优选已经受分子量降低的阴离子改性淀粉。分子量的降低优选酶催进行。降解淀粉的平均摩尔质量Mw例如为500-100 000,优选1000-30 000。降解淀粉的特性粘度[η]例如为0.04-0.5gl/g。这种淀粉例如描述于EP-B-0 257 412和EP-B-0 276 770中。如果保护胶体用于聚合,则以根据聚合中所用的单体,0.5-50,尤其是5-40重量%,通常10-30重量%的量使用。
为了改性聚合物的性能,如果合适的话可在至少一种聚合调节剂的存在下进行聚合。聚合调节剂的实例为以键合形式包含硫的有机化合物,例如十二烷基硫醇、硫二甘醇、乙基硫代乙醇、二(正丁基)硫化物、二(正辛基)硫化物、二苯基硫化物、二异丙基二硫化物、2-巯基乙醇、1,3-巯基丙醇、3-巯基丙烷-1,2-二醇、1,4-巯基丁醇、巯基乙酸、3-巯基丙酸、巯基琥珀酸、硫代乙酸和硫脲,醛如甲醛、乙醛和丙醛,有机酸如甲酸、甲酸钠或甲酸铵,醇尤其如异丙醇,和磷化合物如次磷酸钠。如果在聚合中使用调节剂,则因此每次以例如根据聚合中所用单体,0.01-5,优选0.1-1重量%的量使用。聚合调节剂和交联剂可各自独立地或一起用于聚合。因此,例如可控制产生的聚合物分散体的流变。
细乳液在自由基条件下聚合。聚合通常在至少一种自由基聚合引发剂的存在下进行。所有可引起聚合的化合物适合作为聚合引发剂。就这点而言,它们基本上是过氧化物、氢过氧化物、偶氮化合物和氧化还原催化剂。引发剂的实例可从WO-A-99/40123,第32页第45行至第34页第9行中取得。聚合也可通过高能辐射如UV或光化或放射性辐射作用而引发,如果合适的话,操作可在至少一种敏化剂的存在下进行。细乳液中单体的聚合也可使用微波辐射和/或通过超声波的作用而电化学进行。聚合温度例如为0-120℃,聚合在压力密闭装置中在升高的压力下在大于100℃下进行。细乳液通常在0-95℃下聚合。细乳液中单体的聚合可根据所有已知的聚合方法而进行。它们例如可在单级或在两级或多级过程中进行。
聚合也可例如首先仅使至多50%存在于聚合区的单体聚合。在聚合期间,如果活性物质与形成的聚合物不相容,即活性物质不溶于产生的聚合物或单体与形成的聚合物的混合物中,则可发生活性物质聚集在形成的聚合物粒子的芯中并由聚合物的壳覆盖。然后简单需要给聚合体系足够的时间用于将可发生的活性物质的分离。然后,聚合仅在使活性物质在产生的聚合物粒子的芯中广泛或完全聚集后结束。活性物质与形成的聚合物的分离可在聚合期间使用取出的试样监控。然而,取决于聚合条件,如果合适的话,活性物质也可部分进入水相,在聚合物粒子中形成微区(domains),迁移至聚合物粒子的表面或集中或甚至均匀分布在聚合物的其他地方。
然而,细乳液的聚合也可通过例如将5-30%待聚合的细乳液引入,启动聚合以及在聚合条件下连续或分批计量加入剩余细乳液而单级进行。然而,也可将更少量细乳液引入聚合物区,连续加入剩余细乳液并使之在聚合条件下聚合。
聚合也可以以至少两级进行。为此,包含至少一种活性物质的细乳液首先由如下单体制备:
(a)至少一种在水中溶解度为>0.01g/l的烯属不饱和单体A(在25℃和1013毫巴下),
(b)如果合适的话至少一种在水中溶解度为<0.01g/l的烯属不饱和单体B(在25℃和1013毫巴下),和
(c)如果合适的话,至少一种具有至少两个双键的烯属不饱和单体C,
和至少一种表面活性剂和如果合适的话至少一种疏水性化合物如十氢化萘或聚异丁烯,也可在乳化操作期间或随后将活性物质加入细乳液中,细乳液的单体然后聚合达至多50%的转化率,随后计量加入至少一种分子中具有至少两个双键的烯属不饱和单体(c)的含水粗乳液,聚合完成。
然而,起始原料通常为至少一种活性物质在至少一种单体中的溶液,其首先在至少一种表面活性剂的存在下在水中乳化以得到细乳液。细乳液的单体随后聚合达至多35%的转化率,随后在聚合物条件下加入至少一种分子中具有至少两个双键的烯属不饱和单体(c)的含水粗乳液,剩余单体的聚合完成,或同时或随后计量加入单体(c)。
然而,也可例如通过将一部分细乳液引入,启动聚合,以及在聚合条件下将剩余细乳液连续或分批计量加入而单级进行聚合。
在本发明的另外实施方案中,将对于引发至多25%首先引入的单体而言足够的聚合引发剂加入加热至聚合温度的首先引入的单体(a)和如果合适的话包含至少一种活性物质的(b)的细乳液的混合物中,加入剩余量的这种细乳液和至少一种单体(c)的含水混合物,以及取决于通过加入的引发剂聚合的消耗量,将额外的聚合引发剂计量加入以使剩余单体聚合。
根据可任选使用的(c)交联剂批量计量加入,计量加入可在开始时—在实际聚合开始以前—或在进料过程中在容器中立刻全部进行。如果使用至少两种交联剂,则这些可作为混合物或互相分开,同时或在间隔一段时间计量加入。交联剂也可与单体一起引入细乳液中。然而,它们也可在水中乳化并作为乳液进料一起或在进料操作中与细乳液一起计量加入。就这点而言,有利的是至少一种表面活性剂以保证交联剂乳液的稳定性。
作为细乳液的油相,优选使用:
(a)甲基丙烯酸甲酯、苯乙烯、乙酸乙烯酯、丙烯酸甲酯、甲基丙烯酸乙酯、丙烯酸和/或甲基丙烯酸,
(b)丙烯酸硬脂基酯、丙烯酸月桂基酯和/或丙烯酸棕榈基酯和
(c)二丙烯酸丁二醇酯、四丙烯酸季戊四醇酯、三丙烯酸季戊四醇酯、丙烯酸烯丙基酯、甲基丙烯酸烯丙基酯、二乙烯基苯和/或三丙烯酸三羟甲基丙烷
得到包含活性物质的聚合物水分散体。这些水分散体的固体浓度例如为10-60,优选20-45重量%。聚合物水分散体包含平均粒度为<1000nm,通常<500nm,例如5-450nm,优选10-300nm,尤其是50-250nm的分散粒子。聚合物粒子基本上由聚合物基质组成,并以0.5-60重量%的量包含至少一种农药作为活性物质。由于上述方法产生至少80重量%,优选至少90重量%,特别优选至少95重量%用于在得到的聚合粒子中共聚的活性物质,该量通常对应于细乳液的油相中的用量。
如上已述,农药例如可在聚合物基质中均匀分布或以微区的形式存在于聚合物粒子中。然而,分散粒子也可由芯和壳形成,粒子的芯包含至少一种由聚合物基质的壳覆盖的农药。然而,农药也可从聚合物基质中部分或几乎完全显露出来。它们然后以用表面活性剂稳定的平均大小为约40-400nm的粒子的形式存在于水相中。
包含至少一种农药作为活性物质的聚合物粉末可通过蒸发包含至少一种农药的聚合物水分散体的挥发性组分而从根据本发明方法制备的水分散体中得到。根据本发明制备的分散体和从中得到的聚合物粉末的优点为它们以可控方式释放活性物质并保护它以防分解,即活性物质经相对长期间连续释放,以及极大保护不受外部影响。因此,农药存在于对于它们的应用特别有利的基质中。
包含至少一种农药作为活性物质,例如通过喷雾干燥而从本发明制备的水分散体中得到的聚合物粉末例如为工业上重要的。根据本发明的另外实施方案,可通过使包含至少一种农药的细乳液聚合而得到的水分散体用于植物保护。
根据本发明制备的包含农药的水分散体和通过除去水相而从中可得到的包含至少一种农药的聚合物粉末优选用于农药配制剂中。术语“农药配制剂”在下面进一步阐明。因此,本发明还涉及根据本发明方法制备的分散体用于对抗有害微生物和/或用于调节植物生长和/或用于对抗不想要的植物生长和/或用于对抗不想要的昆虫或螨虫对植物的侵染和/或用于对抗植物病原性真菌和/或用于种子处理的用途。
用于对抗有害微生物和/或用于调节植物生长和/或用于对抗不想要的昆虫或螨虫对植物的侵染和/或用于对抗植物病原性真菌和/或用于种子处理的方法包括用有效量的包含本发明方法制备的分散体或通过除去水相而从中得到的聚合物粉末的农药配制剂处理不想要的微生物、植物病原性真菌/昆虫或螨虫、它们的栖息地或待保护以防微生物、真菌或昆虫侵染的植物、土壤或有用植物的种子。
对抗不想要的植物生长的方法包括用有效量的包含本发明方法制备的分散体或通过除去水相而从中得到的聚合物粉末的农药配制剂处理植物、植物生长的土壤或种子。
对抗不想要的植物生长意指对抗/破坏在不想要它们的地方生长的植物,例如如下类型的双子叶植物:白芥属(Sinapis)、独行菜属(Lepidium)、拉拉藤属(Galium)、繁缕属(Stellaria)、母菊属(Matricaria)、春黄菊属(Anthemis)、牛膝菊属(Galinsoga)、藜属(Chenopodium)、荨麻属(Urtica)、千里光属(Senecio)、苋属(Amaranthus)、马齿苋属(Portulaca)、苍耳属(Xanthium)、旋花属(Convolvulus)、番薯属(Ipomoea)、蓼属(Polygonum)、田菁属(Sesbania)、豚草属(Ambrosia)、蓟属(Cirsium)、飞廉属(Carduus)、苦苣菜属(Sonchus)、茄属(Solanum)、蔊菜属(Rorippa)、节节菜属(Rotala)、母草属(Lindernia)、野芝麻属(Lamium)、婆婆纳属(Veronica)、苘麻属(Abutilon)、刺酸模属(Emex)、曼陀罗属(Datura)、堇菜属(Viola)、鼬瓣花属(Galeopsis)、罂粟属(Papaver)、矢车菊属(Centaurea)、车轴草属(Trifolium)、毛莨属(Ranunculus)、蒲公英属(Taraxacum)。
如下类型的单子叶植物:稗属(Echinochloa)、狗尾草属(Setaria)、黍属(Panicum)、马唐属(Digitaria)、梯牧草属(Phleum)、早熟禾属(Poa)、羊茅属(Festuca)、穆属(Eleusine)、臂形草属(Brachiaria)、黑麦草属(Lolium)、雀麦属(Bromus)、燕麦属(Avena)、莎草属(Cyperus)、高梁属(Sorghum)、冰草属(Agropyron)、狗牙根属(Cynodon)、雨久花属(Monochoria)、Fimbristyslis、慈姑属(Sagittaria)、荸荠属(Eleocharis)、蔗草属(Scirpus)、雀稗属(Paspalum)、鸭嘴草属(Ischaemum)、尖瓣花属(Sphenoclea)、龙爪茅属(Dactyloctenium)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)。
术语“不想要的昆虫或螨虫”描述但不限于如下种类:
鳞翅目(Lepidoptera),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、苹果小卷蛾(Cydiapomonella)、松毛虫(Dendrolimus pini)、黄瓜绢野螟(Diaphania nitidalis)、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoeciliaambiguella)、Evetria bouliana、Feltia subterranea、蜡螟(Galleriamellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholithamolesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothis zea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeuta malinellus)、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygmaexigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletis blancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantriamonacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosomaneustria)、甘蓝夜蛾(Mamestra brassicae)、黄杉毒蛾(Orgyiapseudotsugata)、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophora gossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutella xylostella)、大豆夜蛾(Pseudoplusiaincludens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotrogacerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodopterafrugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodopteralitura)、Thaumatopoea pityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asparagi)、Diabrotica longicornis、Diabrotica 12-punctata、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ipstypographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lemamelanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、Limoniuscalifornicus、稻水象甲(Lissorhoptrus oryzophilus)、玉米叩甲(Melanotuscommuhis)、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolonthahippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulemaoryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、Phyllotretachrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilus granaria);
双翅目(Diptera),例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedesvexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anophelesmaculipennis)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、高梁瘿蚊(Contarinia sorghicola)、Cordylobia anthropophaga、尖音库蚊(Culexpipiens)、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilusintestinalis)、刺舌蝇(Glossina morsitans)、Haematobia irritans、Haplodiplosis equestris、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、葱蝇(Phorbia antiqua)、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasl)、苹果实蝇(Rhagoletis pomonella)、Tabanusbovinus、Tipula oleracea和欧洲大蚊(Tipula paludosa);
缨翅目(Thysanoptera),例如烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci);
膜翅目(Hymenoptera),例如新疆菜叶蜂(Athalia rosae)、切叶蚁(Attacephalotes)、Atta sexdens、Atta texana、Hoplocampa minuta、苹叶蜂(Hoplocampa testudinea)、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsis geminata)和红火蚁(Solenopsis invicta);
异翅目(Heteroptera),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercuscingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygaster integriceps)、Euschistus impictiventris、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezaraviridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis和Thyantaperditor;
同翅目(Homoptera),例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphisforbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphisgrossulariae)、Aphis schneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphon pisum)、马铃薯蚜(Aulacorthum solani)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycauduspersicae、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosipha gossypii、Chaetosiphon fragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulaeorthum pseudosolani、Dysaphis plantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzuslactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphumeuphorbiae)、蔷薇管蚜(Macrosiphon rosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodespersicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzus cerasi、李瘤蚜(Myzusvarians)、Nasonovia ribis-nigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、Rhopalosiphum insertum、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneuralanuginosa、麦长管蚜(Sitobion avenae)、白粉虱(Trialeurodesvaporariorum)、Toxoptera aurantii和葡萄根瘤蚜(Viteus vitifolii);
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、欧洲散白蚁(Reticulitermes lucifugus)和Termes natalensis;
直翅目(Orthoptera)),例如居屋艾蟋(Acheta domestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、欧洲球螋(Forficulaauricularia)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femur-rubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲蟑螂(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、Stauronotus maroccanus和庭疾灶螽(Tachycinesasynamorus);
蜘蛛纲(Arachnoidea),例如蜱螨目(Acarina),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae)如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argaspersicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssus gallinae)、绵羊疥病(Psoroptesovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),和瘿螨属(Eriophyidae spp.)如苹果刺锈螨(Aculusschlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨属(Tarsonemidae spp.)如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨属(Tenuipalpidae spp.)如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae spp.)如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychuscitri)和Oligonychus pratensis;
线虫类(Nematodes),尤其是寄生于植物上的线虫类,例如植物根结线虫,北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyneincognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globodera rostochiensis)和其他球胞囊属(Globodera);禾谷胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)和其他胞囊线虫属(Heterodera);种子肿瘿线虫,粒线虫属(Anguina);茎叶线虫,滑刃线虫属(Aphelenchoides);刺线虫,杂草刺线虫(Belonolaimus longicaudatus)和其他针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchus xylophilus)和其他伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)、中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchus destructor)、甘薯茎线虫(Ditylenchus dipsaci)和其他茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫(spiral nematodes),Heliocotylenchusmulticinctus和其他Helicotylenchus属;鞘线虫和鞘形(sheathoid)线虫,鞘线虫属(Hemicycliophora)和Hemicriconemoides属;Hirshmanniella属;冠线虫,Hoploaimus属;伪根结线虫,珍珠线虫属(Nacobbus);针线虫,Longidorus elongatus和其他长针线虫属(Longidorus);根腐线虫,Pratylenchus neglectus、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchus curvitatus、Pratylenchus goodeyi和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholus similis)和其他穿孔线虫属(Radopholus);肾形线虫,Rotylenchus robustus和其他盘旋线虫属(Rotylenchus);Scutellonema属;残根线虫,Trichodorus primitivus和其他毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,Tylenchorhynchus claytoni、Tylenchorhynchus dubius和其他矮化线虫属(Tylenchorhynchus);柑桔线虫,垫刃线虫属(Tylenchulus);剑线虫,剑线虫属(Xiphinema);
和例如稻病原体,即稻水象甲(rice water weevil)(稻水象甲(Lissorhoptrusoryzaphilus))、水稻二化螟(rice stem borer)(二化螟(Chilo suppresalis))、稻纵卷叶螟(rice leaf roller)、稻负泥甲(rice leaf beetle)、稻潜叶虫(rice leafminer)(Agromyca oryzae)、叶蝉(leafhoppers)(黑尾叶蝉属(Nephotettixspp.));尤其是更小的褐飞虱(brown leafhopper)、稻青大叶蝉(green riceleafhopper)、飞虱(planthoppers)(飞虱科(Delphacidae);尤其是白背飞虱(white backed planthopper)、稻褐飞虱(brown rice planthopper))、蝽(stinkbugs)。
术语“植物病原性真菌”描述但不限于如下物种:
禾谷类中的禾白粉菌(Blumeria graminis)(白粉病),葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerothecafuliginea),苹果上的苹果白粉病菌(Podosphaera leucotricha),葡萄藤上的葡萄钩丝壳(Uncinula necator),禾谷类上的柄锈菌(Puccinia)属,棉花、稻和草坪上的丝核菌(Rhizoctonia)属,禾谷类和甘蔗上的黑粉菌(Ustilago)属,苹果上的黑星病菌(Venturia inaequalis),禾谷类、稻和草坪中的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属,小麦上的颖枯壳针孢(Septorianodorum),草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(Botrytis cinerea),香蕉、花生和禾谷类上的球腔菌(Mycosphaerella)属,小麦和大麦上的眼斑病菌(Pseudocercosporella herpotrichoides),稻上的稻瘟病菌(Pyriculariaoryzae),土豆和西红柿上的致病疫霉(Phytophthora infestans),葫芦科植物和啤酒花上的假霜霉(Pseudoperonospora)属,葡萄藤上的葡萄生单轴霉(Plasmopara viticola),水果和蔬菜上的链格孢(Alternaria)属,以及链孢霉(Fusarium)属和轮枝孢(Verticillium)属,稻类植物和如果合适的话它们的种子上的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属以及稻瘟病菌(Pyricularia oryzae)、笹木伏革菌(Corticium sasakii)(同物异名立枯丝核菌(Rhizoctonia solani))和宫部旋孢腔菌(Cochliobolus miyabeanus),材料如木材上的拟青霉(Paecilomyces variotii)。
使用存在于根据本发明制备的水分散体的聚合物中的农药,可防治不想要的植物生长和/或对抗植物病原性昆虫和/或植物病原性真菌。
包含根据本发明方法可得到的包含农药的聚合物水分散体或如上已述通过除去水相而从根据本发明方法制备的分散体中已制备的聚合物粉末的农药配制剂为本发明的另外主题。
根据本发明方法可得到的包含农药的聚合物水分散体可直接使用或任选包含额外适于配制剂的助剂如表面活性剂(例如润湿剂、粘着剂、乳化剂或分散剂)、消泡剂、增稠剂、载体、防冻剂和杀菌剂。
从根据本发明方法制备的分散体中可得到的聚合物粉末可直接使用或任选包含额外适于配制剂的助剂(例如表面活性剂(例如润湿剂、粘着剂、乳化剂或分散剂)、消泡剂、增稠剂、载体、防冻剂和杀菌剂)和如果合适的话溶剂。
上述试剂的重要性和相应用途取决于所需的配制剂类型和活性物质的性质。
如果使用载体,尤其用于固体配制剂,则它们因此通常以0.1-99重量%,优选10-80重量%的量存在于配制剂中。如果使用它们的话,则配制剂中其他助剂的量例如为0.1-40重量%。
如果使用溶剂,则水,芳族溶剂(如Solvesso产品,二甲苯),石蜡烃(如石油馏分),醇(如甲醇、丁醇、戊醇、苄醇),酮(如环己酮、γ-丁内酯),吡咯烷酮(NMP、NOP),乙酸酯(二乙酸二醇酯),二醇、脂肪酸二甲基酰胺,脂肪酸和脂肪酸酯例如为适合的。原则上也可使用溶剂混合物。
增稠剂(即赋予配制剂以假塑性流动行为,即在静止时粘度高且在搅拌状态下粘度低的化合物)的实例例如为多糖如黄原胶(来自Kelco的Kelzan)、Rhodopol23(-Poulenc)或Veegum(R.T.Vanderbilt)或有机层状矿物如Attagel(Engelhardt)。
例如聚硅氧烷乳液(例如SilikonSRE,Wacker或来自Rhodia的Rhodorsil),长链醇,脂肪酸,有机氟化合物和它们的混合物适合作为消泡剂。
杀菌剂可例如用以稳定含水农药配制剂。合适的杀菌剂例如为来自ICI的Proxel或来自Thor Chemie的ActicideRS和来自Rohm & Haas的KathonMK。
适合的防冻剂例如为乙二醇、丙二醇或甘油。
载体的实例为磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐)。
表面活性剂的实例为木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚;还有磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯脂肪醇醚如聚氧乙烯辛基酚醚,乙氧基化异辛基酚,辛基酚和壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
在聚合物粉末或本发明分散体的基础上制备的配制剂类型的实例为悬浮液、可分散性浓缩物、糊、丸、可湿性粉末、可撒粉粉末(DP)或水溶性或水分散性颗粒(GR、FG、GG、MG)。用于种子处理的标准配制剂类型为FS(流动性浓缩物)、DS(用于干处理的粉末)、WS(用于浆处理的水分散性粉末)、SS(水溶性粉末SS)。这些配制剂的制备和为此所需的技术为本领域技术人员已知的(参看US 3 060 084,EP-A 707 445(对于液体浓缩物),Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,147-48,Perry’s Chemical Engineer’s Handbook,第4版,McGraw-Hill,New York,1963,第8-57及随后各页,WO 91/13546,US 4 172 714,US4 144 050,US 3 920 442,US 5 180 587,US 5 232 701,US 5 208 030,GB 2 095 558,US 3 299 566,Klingman,Weed Control as a Science,JohnWiley and Sons Inc.,New York,1961,Hance等,Weed Control Handbook,第8版,Blackwell Scientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation Technology,Wiley VCH Verlag GmbH,Weinheim(德国),2001,D.A.Knowles,Chemistry and Technology ofAgrochemical Formulations,Kluwer Academic Publishers,Dordrecht,1998(ISBN 0-7514-0443-8)。
颗粒例如为细碎的且与95.5%载体结合。就这点而言标准方法为挤出、喷雾干燥或流化床。由此得到用于直接应用的颗粒。
中至高沸点的石油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、环己醇、环己酮、异佛尔酮或强极性溶剂如二甲亚砜、N-甲基吡咯烷酮或水适于制备可直接喷雾的液体、乳液、糊或油分散体。
粉末、撒播用制剂和粉剂可以通过将包含活性物质的聚合物水分散体或可例如通过喷雾干燥从中得到的粉末与固体载体混合或共同研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过使根据本发明制备的产物粘附在固体载体上而制备。固体载体例如为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵或尿素,以及植物产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。如果需要的话,可将得到的最终产物在额外的处理以前干燥。
本发明还包括已用本发明农药配制剂处理的种子。
术语“种子处理”包括所有通用技术(拌种、种子包覆、种子撒粉、浸种、种子包膜、种子多层包覆、种子包壳、种子滴灌和种子包衣)。
术语“种子”包含所有种类的种子,例如谷类、种子、果实、块茎、插条(cuttings)和相似形式。就这点而言,术语“种子”优选描述谷类和种子。
适合作为种子的有谷类种子、谷类作物种子、块根作物种子、油质种子、蔬菜种子、香料种子或观赏植物种子,例如小麦,包括硬质小麦,大麦、燕麦、黑麦、玉米(饲料玉米和甜玉米)、大豆、油质植物、十字花科植物、棉花、向日葵、香蕉、稻、油菜、芜菁、甜菜、饲料甜菜、茄子、马铃薯、草、草坪、饲料牧草、番茄、韭菜、南瓜、甘蓝、卷心莴苣、胡椒、黄瓜、甜瓜、云苔属(Brassica spp.)、扁豆、豌豆、大蒜、洋葱、胡萝卜、块茎植物如甘蔗、烟草、葡萄、矮牵牛花和老鹳草、三色堇、凤仙花的种子,优选小麦、玉米、大豆和稻的种子。
转基因植物或通过常规育种方法得到的植物的种子也可用作种子。
因此,可使用耐受除草剂、杀真菌剂或杀虫剂的种子,例如耐受磺酰脲类(如EP-A-0 257 993、美国专利No.5 013 659),咪唑啉酮(如US 6 222 100、WO 01/82685、WO 00/26390、WO 97/41218、WO 98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073),草铵膦类型除草剂(如EP-A-0 242 236、EP-A-242 246)或草甘膦类型除草剂(如WO 92/00377)或环己二烯酮/芳氧基苯氧基丙酸类除草剂(如US 5 162 602、US 5 290 696、US 5 498 544、US 5 428 001、US 6 069 298、US 6 268 550、US 6 146 867、US 6 222 099、US 6 414 222);或转基因植物如产生芽孢杆菌(Bacillus thuringiensis)毒素(Bt毒素),并由此耐某些有害生物的棉花(EP-A-0142924、EP-A-0193259)的种子。
此外,还可使用与常规植物相比具有改性性能的植物种子,这些的实例为改性淀粉合成(如WO 92/11376、WO 92/14827、WO 91/19806)或脂肪酸组合物(WO 91/13972)。
在种子处理中通常所用农药的消耗量为0.1-10kg/100kg种子,优选0.1-5kg/100kg,尤其是0.1-2.5kg/100kg。
实施例
实施例中指定的百分数表示重量百分数。细乳液的液滴大小使用Coulter N4 Plus Particle Analyzer在0.01重量%乳液试样上测定。聚合物分散粒子的平均粒度使用Coulter LS 230在0.01重量%水分散体试样上测定。
实施例1
将30g杀真菌剂氧唑菌(epoxiconazole)在环境温度下在15分钟内溶于142.5g甲基丙烯酸甲酯和7.5g丙烯酸硬脂基酯的混合物中。
然后将此溶液引入15g15%月桂基硫酸钠水溶液与663.56g完全去离子的水中,并在其中乳化。随后将因此制备的粗乳液通过使用超声波得到约192nm的液滴大小。此细乳液储存稳定。
将188.74g(总量的24%)细乳液引入反应器中并加热至80℃。然后在80℃下同时加入4.5g2%过硫酸钠水溶液。随后,同时分别进料,每种情况下在60分钟内计量加入597.82g(总量的76%)细乳液以及15g水和7.5g四丙烯酸季戊四醇酯的搅拌混合物(乳液)和0.75g15%的月桂基硫酸钠水溶液。随后将反应混合物在80℃下搅拌另外30分钟。之后,约10%的单体聚合。
为了使剩余单体聚合,经60分钟将70.5g2%过硫酸钠水溶液计量加入加热至80℃的反应混合物中,随后将混合物在80℃下搅拌另外60分钟使后聚合,然后使它冷却至25℃,首先通过500μm,然后通过125μm钢丝网筛过滤以除去凝结物。
因此得到聚合物粒子平均粒度为136nm的聚合物水分散体。如通过干燥水分散体得到的粉状聚合物粒子的电子显微照片所示,粒子为氧唑菌(epoxiconazole)至少部分发现于壳中且聚合物在芯中的芯/壳粒子。分散体储存稳定。
实施例2
将30g杀真菌剂氧唑菌(epoxiconazole)在80℃下在15分钟内溶于190g丙烯酸正丁酯和10g丙烯酸硬脂基酯的混合物中。
然后将此溶液在80℃下引入20g15%月桂基硫酸钠水溶液与844.7g完全去离子的水的溶液中并乳化。随后将因此制备的粗乳液通过在80℃下三次通过APV-Gaulin高压均化器(150巴)得到约200nm的液滴大小。此细乳液稳定储存24小时。
将1098.7g(总量的100%)细乳液在80℃下引入反应器中。然后在80℃下同时加入6g2%过硫酸钠水溶液。随后在60分钟内计量加入20g完全去离子水和10g四丙烯酸季戊四醇酯的搅拌混合物(乳液)和1.0g15%的月桂基硫酸钠水溶液。随后将反应混合物在80℃下搅拌另外30分钟。之后,约10%的单体聚合。
为了完成聚合,经60分钟将94g2%过硫酸钠水溶液计量加入加热至80℃的反应混合物中,随后将混合物在80℃下搅拌另外60分钟使后聚合。聚合可通过加入6g叔丁基过氧化氢和额外的后反应时间而完成。然后使反应混合物冷却至25℃,通过500μm,以及随后125μm钢丝网筛过滤以除去凝结物。
因此得到聚合物粒子平均粒度为134nm的聚合物水分散体。分散体储存稳定。
实施例3
将32.9g粉状杀真菌剂戊叉唑菌(triticonazole)在80℃下在15分钟内溶于190g甲基丙烯酸甲酯和1og丙烯酸硬脂基酯的混合物中。
然后将此溶液在80℃下引入20g15%月桂基硫酸钠水溶液与841.8g完全去离子的水的溶液中并乳化。随后将因此制备的粗乳液通过在80℃下三次通过APV-Gaulin高压均化器(150巴)得到约200nm的液滴大小。此细乳液稳定储存24小时。
将1094.7g(总量的100%)细乳液在80℃下引入反应器中。然后在80℃下同时加入6g2%过硫酸钠水溶液。随后在60分钟内计量加入20g完全去离子的水和1og四丙烯酸季戊四醇酯的搅拌混合物(乳液)和1.0g15%的月桂基硫酸钠水溶液。随后将反应混合物在80℃下搅拌另外30分钟。之后,使约10%的单体聚合。
为了完成聚合,经60分钟将94g2%过硫酸钠水溶液计量加入加热至80℃的反应混合物中,随后将混合物在80℃下搅拌另外60分钟使后聚合。聚合可通过加入8g叔丁基过氧化氢和额外的后反应时间而完成。然后使反应混合物冷却至25℃,通过500μm,以及随后125μm钢丝网筛过滤以除去凝结物。
得到聚合物粒子的平均粒度为131nm的聚合物水分散体,聚合物粒子基本包含所有聚合中所用的杀真菌剂。分散体储存稳定。
Claims (15)
1.一种通过水包油乳液的自由基聚合而制备包含农药且分散粒子的平均粒度为<1000nm的聚合物水分散体的方法,其中乳液的油相包含在至少一种烯属不饱和单体中的至少一种农药,该方法包括使至少一种农药在至少一种单体中的溶液在至少一种表面活性剂的存在下在水中乳化以得到平均液滴大小为<500nm的细乳液,和/或在乳化期间或其后加入至少一种农药,以及随后使细乳液在自由基条件下聚合。
2.根据权利要求1的方法,其中作为烯属不饱和单体,使用:
(a)50-100重量%至少一种在25℃和1013毫巴下在水中的溶解度为>0.01g/l的烯属不饱和单体A,
(b)0-50重量%至少一种在25℃和1013毫巴下在水中的溶解度为<0.01g/l的烯属不饱和单体B,和
(c)0-30重量%至少一种具有至少两个双键的烯属不饱和单体C。
3.根据权利要求1或2的方法,其中作为烯属不饱和单体,使用:
(a)甲基丙烯酸甲酯、苯乙烯、乙酸乙烯酯、丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸和/或甲基丙烯酸、丙烯酰胺、甲基丙烯酰胺、丙烯腈和甲基丙烯腈,
(b)如果合适的话,丙烯酸月桂基酯、丙烯酸棕榈基酯和/或丙烯酸硬脂基酯,和
(c)如果合适的话,二丙烯酸丁二醇酯、丙烯酸烯丙基酯、甲基丙烯酸烯丙基酯、三丙烯酸三羟甲基丙烷、二乙烯基苯、三丙烯酸季戊四醇酯和/或四丙烯酸季戊四醇酯。
4.根据权利要求1-3中任一项的方法,其中作为烯属不饱和单体,使用:
(a)甲基丙烯酸甲酯、甲基丙烯酸乙酯和/或丙烯酸,和
(c)二丙烯酸丁二醇酯、四丙烯酸季戊四醇酯、三丙烯酸季戊四醇酯、三丙烯酸三羟甲基丙烷、甲基丙烯酸烯丙基酯和/或丙烯酸烯丙基酯。
5.根据权利要求1-4中任一项的方法,其中在乳化操作期间加入至少一种活性物质,然后使细乳液的单体聚合达至多50%的转化率,随后在聚合物条件下计量加入至少一种分子中具有至少两个双键的烯属不饱和单体(c)的含水粗乳液,以及细乳液的剩余单体的聚合同时或随后完成。
6.根据权利要求1-4中任一项的方法,其中使至少一种活性物质在至少一种单体中的溶液在至少一种表面活性剂的存在下在水中乳化以得到细乳液,细乳液的单体聚合达至多35%的转化率,随后在聚合物条件下计量加入至少一种分子中具有至少两个双键的烯属不饱和单体(c)的含水粗乳液,以及细乳液的剩余单体的聚合同时或随后完成。
7.根据权利要求5或6的方法,其中所述细乳液的单体首先聚合达至多25%的转化率。
8.根据权利要求1-7中任一项的方法,其中所述细乳液的油相包含根据所用单体的总量,0.5-60重量%的至少一种农药。
9.根据权利要求1-8中任一项的方法,其中所述至少一种活性物质在至少一种单体中的溶液在至少一种不可聚合的疏水性化合物的存在下在水中乳化。
10.一种可根据权利要求1-9中任一项的方法而得到的水分散体。
11.一种农业化学配制剂,其包含可根据权利要求1-9中任一项的方法而得到的水分散体或可通过蒸发挥发性组分而从中得到的聚合物粉末。
12.可根据权利要求1-9中任一项的方法而得到的分散体和可通过蒸发挥发性组分而从中得到的包含至少一种农药的聚合物粉末在对抗有害微生物和/或在调节植物生长和/或在对抗不想要的植物生长和/或在对抗不想要的昆虫或螨虫对植物的侵染和/或在对抗植物病原性真菌和/或在种子处理中的用途。
13.一种用于对抗有害微生物和/或用于调节植物生长和/或用于对抗不想要的植物生长和/或用于对抗不想要的昆虫或螨虫的侵染和/或用于对抗植物病原性真菌和/或用于种子处理的方法,其包括用有效量的根据权利要求11的农药配制剂处理不想要的微生物、植物病原性真菌和/或昆虫或螨虫、它们的栖息地或待保护以防微生物、真菌侵染或昆虫或螨虫侵染的植物、土壤或有用植物的种子。
14.一种用于对抗不想要的植物生长的方法,其包括用有效量的根据权利要求11的农药配制剂处理植物、土壤或它们的种子。
15.一种用至少一种根据权利要求11的农业化学配制剂处理的种子。
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2006
- 2006-03-07 CA CA2600285A patent/CA2600285C/en not_active Expired - Fee Related
- 2006-03-07 CN CNA2006800159539A patent/CN101170903A/zh active Pending
- 2006-03-07 US US11/908,234 patent/US20080171658A1/en not_active Abandoned
- 2006-03-07 EP EP06708666.0A patent/EP1858320B1/de not_active Not-in-force
- 2006-03-07 WO PCT/EP2006/060516 patent/WO2006094978A2/de active Application Filing
- 2006-03-07 RU RU2007137187/15A patent/RU2369093C2/ru not_active IP Right Cessation
- 2006-03-07 JP JP2008500183A patent/JP2008532978A/ja active Pending
- 2006-03-07 ES ES06708666T patent/ES2715977T3/es active Active
- 2006-03-07 BR BRPI0609170-9A patent/BRPI0609170A2/pt not_active IP Right Cessation
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2007
- 2007-09-06 IL IL185778A patent/IL185778A0/en unknown
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103458686A (zh) * | 2011-04-08 | 2013-12-18 | 巴斯夫欧洲公司 | 含有农药和乙烯基咪唑三元共聚物的组合物 |
CN103458686B (zh) * | 2011-04-08 | 2015-04-15 | 巴斯夫欧洲公司 | 含有农药和乙烯基咪唑三元共聚物的组合物 |
CN103957702A (zh) * | 2011-10-27 | 2014-07-30 | 先正达参股股份有限公司 | 配制品 |
CN103957702B (zh) * | 2011-10-27 | 2017-05-31 | 先正达参股股份有限公司 | 配制品 |
CN104023527A (zh) * | 2011-12-28 | 2014-09-03 | 日本环境化学株式会社 | 缓释性粒子、木材处理剂及其制造方法 |
CN106342797A (zh) * | 2011-12-28 | 2017-01-25 | 大阪煤气化学株式会社 | 缓释性粒子及其制造方法、木材处理剂及乳浊液的制造方法 |
US20210127665A1 (en) * | 2019-10-31 | 2021-05-06 | Winfield Solutions, Llc | Drift reduction adjuvants and methods of using the same |
US11737455B2 (en) * | 2019-10-31 | 2023-08-29 | Winfield Solutions, Llc | Drift reduction adjuvants and methods of using the same |
Also Published As
Publication number | Publication date |
---|---|
RU2007137187A (ru) | 2009-04-20 |
ES2715977T3 (es) | 2019-06-07 |
US20080171658A1 (en) | 2008-07-17 |
ZA200708553B (en) | 2009-11-25 |
EP1858320A2 (de) | 2007-11-28 |
RU2369093C2 (ru) | 2009-10-10 |
BRPI0609170A2 (pt) | 2010-11-16 |
EP1858320B1 (de) | 2018-12-19 |
CA2600285C (en) | 2013-10-15 |
WO2006094978A3 (de) | 2007-07-12 |
CA2600285A1 (en) | 2006-09-14 |
IL185778A0 (en) | 2008-01-06 |
WO2006094978A2 (de) | 2006-09-14 |
JP2008532978A (ja) | 2008-08-21 |
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