CN101160047A - 含有至少一种康唑杀真菌剂、其他杀真菌剂和稳定性共聚物的制剂 - Google Patents
含有至少一种康唑杀真菌剂、其他杀真菌剂和稳定性共聚物的制剂 Download PDFInfo
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- CN101160047A CN101160047A CNA200680012809XA CN200680012809A CN101160047A CN 101160047 A CN101160047 A CN 101160047A CN A200680012809X A CNA200680012809X A CN A200680012809XA CN 200680012809 A CN200680012809 A CN 200680012809A CN 101160047 A CN101160047 A CN 101160047A
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
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- 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
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
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Abstract
本发明涉及制剂,尤其是植物保护制剂,其包含至少两种不同的植物保护活性物质的混合物,其中a)至少一种活性物质选自康唑(活性物质1),和b)另一植物保护活性物质(活性物质2)在20℃的温度下在水中的溶解度低于20g/l,c)至少一种由单体M构成的共聚物CP,其中单体M包含α)至少一种含有至少一个磺酸基团的单烯属不饱和单体M1和β)至少一种中性单烯属不饱和单体M2,其中活性物质1与其他植物保护活性物质2的比例为1∶10-10∶1。本发明还涉及新型共聚物CP,其呈由至少三种不同的单烯属不饱和单体M构成的聚合物形式且以聚合掺入形式包含α)至少一种含有至少一个磺酸基团的单烯属不饱和单体M1,β1)至少一种在20℃的温度下在水中的溶解度低于30g/l的中性单烯属不饱和单体M2,和β2)至少一种在20℃的温度下在水中的溶解度高于50g/l的中性单烯属不饱和单体M2b。
Description
本发明涉及包含至少一种康唑(conazole)杀真菌剂,尤其是氧唑菌(epoxiconazole)和至少一种其他活性化合物的制剂,尤其是用于作物保护的制剂。
为了在作物保护和材料保护中施用,希望以可以容易地用水稀释至施用所需低浓度的制剂形式配制杀真菌活性化合物。除了其中活性化合物与表面活性剂一起溶解或悬浮于通常不与水溶混的有机溶剂或油中的含溶剂的乳油(EC)以外,还可以提到其中活性化合物以与表面活性剂一起的细碎悬浮液形式存在的悬浮浓缩物(SC)。还已知水分散性粉末(WP)和具有至少一种第一活性化合物固相和至少一种悬浮/乳化于水相中的其他有机液相的悬浮乳液(SE)。
原则上讲,EC的缺点是它们包含较大量的有机溶剂,这一方面增加生产成本并在储存和处理过程中导致额外的危险。与EC相反,悬浮浓缩物本身仅包含少量挥发性有机化合物;然而,它们的缺点是储存稳定性低,尤其是当活性化合物倾向于结晶时,如在氧唑菌的情况下。悬浮乳液除了不能不考虑的挥发性不可燃有机溶剂的含量外又具有如下缺点:这些复合多相体系热力学上不稳定,从而使得一方面储存稳定性通常并不令人满意且有机组分在用水稀释时可能存在或存在不可控的絮凝和沉淀的形成。
常规水可稀释活性化合物制剂如SC、EC和SE的另一缺点为分别悬浮和乳化在水相中的活性化合物颗粒或活性化合物液滴在用水稀释制剂后具有通常为几个μm的较大粒度这一事实。然而,希望在用水将配制剂稀释至施用所需浓度之后,活性化合物以尽可能精细分布的形式存在于所得含水制剂中,从而一方面确保在配制剂中的均匀分布并因此确保更好的处理和投料性能,同时增加活性化合物在配制剂中的生物利用率。这里的目标是其中非均相的平均粒度低于500nm的配制剂。
康唑杀真菌剂是具有咪唑或三唑基的有机活性化合物,其杀真菌作用正如已知的那样基于对麦角甾醇生物合成的抑制且因此对选自子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)和半知菌纲(Deuteromycetes)的许多植物损害性真菌有效。氧唑菌(rel-1-[[(2R,3S)-3-(2-氯苯基)-2-(4-氟苯基)环氧乙烷基]甲基]-1H-1,2,4-三唑的通用名)例如为唑类杀真菌剂中最近发现的活性化合物。
为了拓宽其活性谱并增强其杀真菌活性,通常将康唑杀真菌剂与其他活性化合物一起配制。这可能导致问题的出现,尤其在其他活性化合物仅在水中具有低溶解度时。
WO 03/055944描述了基于丙烯酰胺基甲基丙烷磺酸(AMPS)的共聚物在作物保护用含水悬浮浓缩物中作为结晶抑制剂的用途。
较早的专利申请PCT/EP 04/011797公开了活性化合物配制剂,其包含至少一种活性化合物和至少一种可以通过烯属不饱和磺酸与丙烯酸或甲基丙烯酸的酯或酰胺自由基聚合得到的无规共聚物。
因此,本发明的目的是提供康唑杀真菌剂,尤其是氧唑菌的制剂,该制剂可以分散于水中或者可以容易地用水稀释而不发生不利的分离。该制剂应包含最小可能量的有机溶剂并还应确保活性化合物在稀释时精细地分散在水相中。还希望具有高度储存稳定性。
该目的由一种制剂实现,该制剂除了至少一种康唑杀真菌剂(活性化合物1)外还包含至少一种在20℃下在水中的溶解度低于20g/l的其他作物保护剂2和由烯属不饱和单体M构成的至少一种共聚物CP,其中构成共聚物CP的单体M包含:
α)至少一种具有至少一个磺酸基团的单烯属不饱和单体M1,和
β)至少一种中性单烯属不饱和单体M2,
其中活性化合物1与至少一种其他作物保护剂2的比例为1∶10-10∶1。
因此,本发明涉及包含至少两种不同作物保护剂的混合物的制剂,其中
a)至少一种活性化合物选自康唑(活性化合物1),和
b)至少一种在20℃下在水中的溶解度低于20g/l的其他作物保护剂(活性化合物2),
进一步包含
c)至少一种由烯属不饱和单体M构成的共聚物CP,其中单体M包含:
α)至少一种具有至少一个磺酸基团的单烯属不饱和单体M1,和
β)至少一种中性单烯属不饱和单体M2,
其中活性化合物1与至少一种其他作物保护剂2的比例为1∶10-10∶1。
本发明制剂以有利方式适于在水相中稳定至少一种康唑杀真菌剂,尤其氧唑菌,与活性化合物2的混合物而不需要任何有机溶剂。与现有技术中所述的悬浮乳液相反,用水稀释本发明制剂得到其中氧唑菌和至少一种其它活性化合物2以极细碎或甚至分子分散形式存在于连续水相中的含水配制剂。假定活性化合物与共聚物CP在水相中形成聚集体。这些聚集体通常具有的平均粒度低于500nm,特别低于400nm,尤其低于300nm,非常特别低于200nm。当稀释本发明制剂时,若存在的话,由于凝结、结晶、絮凝或沉降引起的不均匀和不稳定非常低。此外,假设是由于活性化合物在含水施用形式中极细的分散,对应于活性化合物聚集体非常低的表观粒径,活性化合物的活性与唑类杀真菌剂,尤其是氧唑菌的常规配制剂相比增加。
所述粒度为可以通过动态光散射测定的重均粒度。本领域熟练技术人员熟知进行该测定的方法,例如由H.Wiese,D.Distler,WssrigePolymerdispersionen[聚合物水分散体],Wiley-VCH 1999,第4.2.1章,第40页及随后各页和其中所引用的文献以及H.Auweter,D.Horn,J.ColloidInterf.Sci.105(1985)399,D.Lilge,D.Horn,Colloid Polym.Sci.269(1991)704或H.Wiese,D.Horn,J.Chem.Phys.94(1991)6429已知。
作为活性化合物1,本发明的制剂包含至少一种康唑杀真菌剂(参见http://www.hclrss.demon.co.uk/class_fungicides.html)。已知康唑杀真菌剂包括某些咪唑化合物,如同菌唑(climbazole)、克霉唑(clotrimazole)、烯菌灵(imazalil)、咪唑(oxpoconazole)、丙氯灵(prochloraz)和氟菌唑(triflumizole),以及某些三唑化合物,如戊环唑(azaconazole)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、苄氯三唑醇(dichlobutrazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、氧唑菌、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、唑喹菌酮(quinconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、戊叉唑菌(triticonazole)、三唑酮(triadimefone)、唑菌醇(triadimenole)和烯效唑(uniconazole)。活性化合物1特别为上述三唑化合物之一,尤其是环唑醇、氧唑菌、喹唑菌酮、己唑醇、环戊唑菌、戊菌唑、丙环唑、丙硫菌唑、戊唑醇和戊叉唑菌。在特别优选的实施方案中,活性化合物1为氧唑菌。在另一特别优选的实施方案中,活性化合物1为环戊唑菌。
此外,本发明的活性化合物制剂包含至少一种,例如1或2种其他活性化合物2,该活性化合物在20℃下在水中的溶解度低于20g/l,特别低于10g/l,尤其低于5g/l。活性化合物2尤其为杀真菌活性化合物。然而,它们原则上还可以是不同于杀真菌剂的活性化合物,例如杀虫剂、杀螨剂、除草剂、杀线虫剂或生长调节剂。必要的是活性化合物1和活性化合物2不同,至少一种活性化合物为康唑杀真菌剂且其他活性化合物在20℃下在水中的溶解度低于20g/l。合适的活性化合物2对本领域熟练技术人员是已知的;例如参见http://www.hclrss.demon.co.uk/index.html。
在本发明的优选实施方案中,活性化合物2的熔点低于70℃(在大气压力下)。
本发明优选的杀真菌活性化合物2的实例例如为:
-嗜球果伞素类(strobilurin)杀真菌剂,如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、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)和肟菌酯(trifloxystrobin),尤其是唑菌胺酯,
-吗啉杀真菌剂,如aldamorph、苯杂吗(benzamorf)、卡巴莫夫(carbamorph)、吗菌灵(dodemorph)、烯酰吗啉(dimethomorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、氟吗啉(flumorph)和克啉菌(tridemorph),
-百菌清(chlorothalonil),
-啶酰菌胺(boscalid),
-非分类的杀真菌剂,选自螺茂胺(spiroxamine)和苯菌酮(metrafenone),以及
-不同于组合物中所存在的活性化合物1的上述康唑杀真菌剂,尤其是丙氯灵、环唑醇、喹唑菌酮、己唑醇、环戊唑菌、戊菌唑、丙环唑、丙硫菌唑、戊唑醇和戊叉唑菌,尤其是环戊唑菌、喹唑菌酮和丙硫菌唑。
在特别优选的实施方案中,活性化合物2为唑菌胺酯。在另一特别优选的实施方案中,活性化合物2为上述康唑杀真菌剂之一,尤其是丙氯灵、环唑醇、喹唑菌酮、己唑醇、环戊唑菌、戊菌唑、丙环唑、丙硫菌唑、戊唑醇和戊叉唑菌,特别是环戊唑菌、喹唑菌酮和丙硫菌唑。
活性化合物1和2尤其为作为活性化合物1的氧唑菌与作为活性化合物2的至少一种嗜球果伞素类,尤其是唑菌胺酯以及合适的话一种其他活性化合物,例如苯锈啶的组合,或者作为活性化合物1的氧唑菌与作为活性化合物2的至少一种不同于氧唑菌的其他康唑杀真菌剂,尤其是选自丙氯灵、环唑醇、喹唑菌酮、己唑醇、环戊唑菌、戊菌唑、丙环唑、丙硫菌唑、戊唑醇和戊叉唑菌,特别是环戊唑菌、喹唑菌酮和丙硫菌唑的康唑杀真菌剂的组合。
另一优选实施方案涉及包含环戊唑菌作为活性化合物1和嗜球果伞素类,尤其是唑菌胺酯作为活性化合物2的制剂。
在本发明制剂中,康唑杀真菌剂与至少一种其他活性化合物2的比例优选为1∶8-8∶1,特别是5∶1-1∶5,尤其是1∶3-3∶1。
根据本发明,该制剂包含至少一种在水相中稳定活性化合物的共聚物CP。通常而言,本发明制剂基于1重量份活性化合物的总量,即活性化合物1和活性化合物2的总量以0.1-10重量份(对应于10-1000重量%,基于活性化合物1和活性化合物2的总量),特别是0.5-8重量份,尤其是1-5重量份,的量包含共聚物CP。
共聚物CP通常为所谓的无规共聚物,即单体M1和M2以无规方式分布在聚合物链上。原则上讲,交替共聚物CP和嵌段共聚物CP也是合适的。
根据本发明,构成共聚物CP的单体M包含至少一种具有至少一个磺酸基团的单烯属不饱和单体M1。单体M1在单体M中的比例基于单体M的总量通常为1-90重量%,常常为1-80重量%,特别是2-70重量%,尤其是5-60重量%。
合适的单体M1原则上为所有具有至少一个磺酸基团的单烯属不饱和单体。单体M1可以其酸形式和盐形式存在。所述重量份指酸形式。
单体M1的实例是苯乙烯磺酸、乙烯基磺酸、烯丙基磺酸、甲代烯丙基磺酸以及下式I所定义的单体和上述单体1的盐。
在式I中:
n为0、1、2或3,尤其是1或2;
X为O或NR5;
R1为氢或甲基;
R2、R3相互独立地为氢或C1-C4烷基,尤其是氢或甲基,和
R5为氢或C1-C4烷基,尤其是氢。
式I的单体M1的实例是2-丙烯酰胺基-2-甲基丙烷磺酸、2-甲基丙烯酰胺基-2-甲基丙烷磺酸、2-丙烯酰胺基乙烷磺酸、2-甲基丙烯酰胺基乙烷磺酸、2-丙烯酰氧基乙烷磺酸、2-甲基丙烯酰氧基乙烷磺酸、3-丙烯酰氧基丙烷磺酸和2-甲基丙烯酰氧基丙烷磺酸。
若单体M1以其盐形式存在,则它们具有对应的阳离子作为抗衡离子。合适的阳离子实例是碱金属阳离子,如Na+或K+,碱土金属离子,如Ca2+和Mg2+,此外还有铵离子,如NH4 +,四烷基铵阳离子,如四甲基铵、四乙基铵和四丁基铵,此外还有质子化的伯、仲和叔胺,尤其是带有1、2或3个选自C1-C20烷基和羟基乙基的基团的那些,例如单-、二-和三丁基胺、丙基胺、二异丙基胺、己基胺、十二烷基胺、油基胺、硬脂基胺、乙氧基化油基胺、乙氧基化硬脂基胺、乙醇胺、二乙醇胺、三乙醇胺或N,N-二甲基乙醇胺的质子化形式。
除了单体M1外,构成共聚物CP的单体M包含至少一种中性单烯属不饱和单体M2。中性是指单体M2不具有以离子形式存在或在含水介质中发生酸性或碱性反应的官能基团。单体M2的总量基于单体M的总重量通常为10-99重量%,常常为20-99重量%,特别是30-98重量%,尤其是40-95重量%。
单体M2的实例是在水中具有有限溶解度,例如在水中的溶解度低于50g/l,尤其低于30g/l(在20℃和1013毫巴下)的那些以及在水中具有增加的溶解度,例如在水中的溶解度≥50g/l,尤其≥80g/l(在20℃和1013毫巴下)的那些。下文中将在水中具有有限溶解度的单体也称为单体M2a。下文中将在水中具有增加的溶解度的单体也称为单体M2b。
单体M2a的实例是乙烯基芳族单体,如苯乙烯和苯乙烯衍生物,如α-甲基苯乙烯、乙烯基甲苯、邻甲基苯乙烯、间甲基苯乙烯和对甲基苯乙烯,乙基乙烯基苯,乙烯基萘,乙烯基二甲苯,还有对应的卤代乙烯基芳族单体,具有2-12个碳原子的α-烯烃,如乙烯、丙烯、1-丁烯、1-戊烯、1-己烯、异丁烯、二异丁烯等,二烯烃,如丁二烯和异戊二烯,脂族C1-C18羧酸的乙烯基酯,如乙酸乙烯酯、丙酸乙烯酯、月桂酸乙烯酯和硬脂酸乙烯酯,乙烯基卤,如氯乙烯、氟乙烯、偏二氯乙烯、偏二氟乙烯,单烯属不饱和单羧酸和二羧酸如丙烯酸、甲基丙烯酸、富马酸、马来酸或衣康酸的单-和二-C1-C24烷基酯,上述单烯属不饱和单羧酸和二羧酸的单-和二-C5-C12环烷基酯,上述单烯属不饱和单羧酸和二羧酸与苯基-C1-C4链烷醇或苯氧基-C1-C4链烷醇的单酯和二酯,此外还有单烯属不饱和醚,尤其是C1-C20烷基乙烯基醚,如乙基乙烯基醚、甲基乙烯基醚、正丁基乙烯基醚、十八烷基乙烯基醚、三甘醇乙烯基甲基醚、乙烯基异丁基醚、乙烯基2-乙基己基醚、乙烯基丙基醚、乙烯基异丙基醚、乙烯基十二烷基醚、乙烯基叔丁基醚。
单体M2a优选选自乙烯基芳族单体,丙烯酸与C2-C20链烷醇,尤其是C2-C10链烷醇的酯,如丙烯酸乙酯、丙烯酸正丁基酯、丙烯酸2-丁基酯、丙烯酸异丁基酯、丙烯酸叔丁基酯、丙烯酸2-乙基己基酯、丙烯酸癸基酯、丙烯酸月桂基酯和丙烯酸硬脂基酯,丙烯酸与C4-C10环烷醇的酯,如丙烯酸环己基酯,丙烯酸与苯基-C1-C4链烷醇的酯,如丙烯酸苄基酯、丙烯酸2-苯基乙基酯和丙烯酸1-苯基乙基酯,丙烯酸与苯氧基-C1-C4链烷醇的酯,如丙烯酸2-苯氧基乙基酯,甲基丙烯酸与C1-C20链烷醇,优选C1-C10链烷醇,尤其是C1-C6链烷醇的酯,如甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丁基酯、甲基丙烯酸2-丁基酯、甲基丙烯酸异丁基酯、甲基丙烯酸叔丁基酯、甲基丙烯酸2-乙基己基酯、甲基丙烯酸癸基酯、甲基丙烯酸月桂基酯和甲基丙烯酸硬脂基酯,甲基丙烯酸与C4-C10环烷醇的酯,如甲基丙烯酸环己基酯,甲基丙烯酸与苯基-C1-C4链烷醇的酯,如甲基丙烯酸苄基酯、甲基丙烯酸2-苯基乙基酯和甲基丙烯酸1-苯基乙基酯,以及甲基丙烯酸与苯氧基-C1-C4链烷醇的酯,如甲基丙烯酸2-苯氧基乙基酯。在特别优选的实施方案中,单体M2a基于单体M2a的总量包含至少80%,尤其是仅包含丙烯酸和/或甲基丙烯酸与C1-C6链烷醇的酯。
在水中具有增加的溶解性或甚至具有水溶混性的中性烯属不饱和单体对本领域熟练技术人员而言是已知的,例如由Ullmann’s Encyclopedia ofIndustrial Chemistry,“聚丙烯酸酯”,第5版,CD-ROM,Wiley-VCH,Weinheim 1997已知。典型的单体M2b是单烯属不饱和单羧酸,尤其是丙烯酸和甲基丙烯酸的羟基-C2-C4烷基酯,如丙烯酸2-羟基乙基酯、丙烯酸2-羟基丙基酯、丙烯酸3-羟基丙基酯、丙烯酸2-羟基丁基酯、丙烯酸4-羟基丁基酯、甲基丙烯酸2-羟基乙基酯、甲基丙烯酸2-羟基丙基酯、甲基丙烯酸3-羟基丙基酯、甲基丙烯酸2-羟基丁基酯、甲基丙烯酸4-羟基丁基酯,此外还有单烯属不饱和单羧酸的酰胺,如丙烯酰胺、甲基丙烯酰胺,此外还有丙烯腈和甲基丙烯腈,N-乙烯基内酰胺,如N-乙烯基吡咯烷酮、N-乙烯基己内酰胺,脂族C1-C4单羧酸的N-乙烯基酰胺,如N-乙烯基甲酰胺、N-乙烯基乙酰胺,带有脲基的单烯属不饱和单体,如N-乙烯基-和N-烯丙基脲,还有咪唑烷-2-酮的衍生物,例如N-乙烯基-和N-烯丙基咪唑烷-2-酮、N-乙烯氧基乙基咪唑烷-2-酮、N-烯丙氧基乙基咪唑烷-2-酮、N-(2-丙烯酰胺基乙基)咪唑烷-2-酮、N-(2-丙烯酰氧基乙基)咪唑烷-2-酮、N-(2-甲基丙烯酰胺基乙基)咪唑烷-2-酮、N-(2-甲基丙烯酰氧基乙基)咪唑烷-2-酮(=脲基甲基丙烯酸酯)、N-[2-(丙烯酰氧基乙酰胺基)乙基]咪唑烷-2-酮、N-[2-(2-丙烯酰氧基乙酰胺基)乙基]咪唑烷-2-酮、N-[2-(2-甲基丙烯酰氧基乙酰胺基)乙基]咪唑烷-2-酮等等。单体M2b优选选自丙烯酸和甲基丙烯酸的羟基-C1-C4烷基酯,丙烯酰胺,甲基丙烯酰胺,丙烯腈,N-乙烯基内酰胺,特别优选丙烯酸和甲基丙烯酸的羟基-C2-C4烷基酯。单体M2b尤其包含基于单体M2b的总量为至少80重量%的至少一种丙烯酸和/或甲基丙烯酸的羟基-C2-C4烷基酯。
单体M2优选包含至少一种在20℃的水中的溶解度低于50g/l,尤其低于30g/l的上述单体M2a。单体M2a在构成共聚物CP的单体M中的比例基于单体M的总重量通常为10-99重量%,常常为20-99重量%,特别是30-98重量%,尤其是40-95重量%。
在另一优选实施方案中,单体M2选自丙烯酸甲酯以及丙烯酸甲酯与上述单体M2a和/或M2b的混合物。这里丙烯酸甲酯或甲基丙烯酸甲酯与单体M2b的混合物的量通常为单体总量的10-99重量%,特别是20-98重量%,尤其是40-95重量%。
在本发明的第一优选实施方案中,单体M2a为唯一的或几乎唯一的单体M2且占单体M2的至少95重量%,尤其是至少99重量%。
该第一实施方案的特殊方面涉及其中共聚物CP包含作为单体M2a的至少一种第一单烯属不饱和单体M2a(1)和至少一种与其不同的单体M2a(2)的制剂。单体M2a(1)为在20℃和1013毫巴下在水中的溶解度为1-<50g/l,尤其是5-30g/l的单体。优选的单体M2a(1)为丙烯酸C2-C4烷基酯和甲基丙烯酸C1-C4烷基酯,尤其是甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丙基酯,特别是甲基丙烯酸甲酯。单体M2a(2)为在20℃和1013毫巴下在水中的溶解度低于1g/l,尤其低于0.5g/l的单烯属不饱和单体。优选的单体M2a(2)为丙烯酸和甲基丙烯酸与C6-C20链烷醇,尤其是C8-C18链烷醇的酯,如丙烯酸正辛基酯、甲基丙烯酸正辛基酯、丙烯酸癸基酯、甲基丙烯酸癸基酯、丙烯酸月桂基酯、甲基丙烯酸月桂基酯、丙烯酸肉豆蔻基酯、甲基丙烯酸肉豆蔻基酯、丙烯酸鲸蜡基酯、甲基丙烯酸鲸蜡基酯、丙烯酸硬脂基酯和甲基丙烯酸硬脂基酯。单体M2a(1)的量基于单体M的总量通常为10-98重量%,尤其是20-90重量%。单体M2a(2)的量基于单体M的总量通常为1-89重量%,尤其是5-60重量%。在该实施方案中,单体M1的量基于单体M的总量通常为1-89重量%,尤其是5-60重量%。
在本发明的第二优选实施方案中,单体M2除了单体M2a外还包含至少一种在20℃下在水中的溶解度为至少50g/l,尤其是至少80g/l的单体M2b。相应地,构成共聚物CP的单体M除了单体M1外还包含至少一种上述单体M2a,尤其是至少一种优选的上述单体M2a和至少一种上述单体M2b,尤其是至少一种优选的上述单体M2b。该类共聚物是新的且也形成本发明主题的一部分。
通常而言,单体M1+M2b的总量基于单体M的总量不超过90重量%,特别是80重量%,尤其是70重量%且基于单体M的总量尤其为10-90重量%,特别是20-80重量%,尤其是30-70重量%。相应地,单体M2a基于单体M的总量通常占至少10重量%,特别是至少20重量%,尤其是至少30重量%,例如10-90重量%,特别是20-80重量%,尤其是30-70重量%。
在第二个特别优选的实施方案中,基于单体M的总量,单体M1优选占1-80重量%,尤其2-70重量%,特别优选5-60重量%,单体M2a优选占10-90重量%,尤其20-80重量%,特别优选30-70重量%且单体M2b优选占5-89重量%,尤其10-78重量%,特别优选20-65重量%。其中特别优选其构成单体M包含至少一种式I单体作为单体M1、至少一种选自丙烯酸与C2-C10链烷醇的酯和甲基丙烯酸与C1-C10链烷醇的酯的单体作为单体M2a以及至少一种选自丙烯酸和甲基丙烯酸的羟基-C2-C4烷基酯的单体作为单体M2b的共聚物CP。
在本发明的第三优选实施方案中,构成共聚物CP的单体包含丙烯酸甲酯或丙烯酸甲酯与至少一种上述单体M2b的混合物作为单体M2。基于单体总量,单体M1的量在上述范围内,通常为1-90重量%,特别是2-80重量%,尤其是5-60重量%。丙烯酸甲酯和任何所用单体M2b的总量基于单体M的总量通常为10-99重量%,尤其是20-98重量%,特别是40-95重量%。对于优选的单体M2b,上面所述内容适用。在丙烯酸甲酯与单体M2b的混合物中,丙烯酸甲酯:单体M2b的重量比通常为10∶1-1∶1,尤其是5∶1-1.2∶1。
此外,构成共聚物的单体M可以包含不同于单体M1和M2的其他单体M3。单体M3在单体M的总量中的比例优选不超过40重量%,尤其不超过20重量%。在优选实施方案中,单体不包含或包含不超过3重量%,尤其不超过1重量%的不同于单体M1和M2的单体M3。
单体M3包括具有至少一个羧酸基团的单烯属不饱和单体,尤其是具有3-6个碳原子的单烯属不饱和单羧酸和二羧酸(单体M3a),如丙烯酸、甲基丙烯酸、乙烯基乙酸、巴豆酸、富马酸、马来酸、衣康酸等,以及上述单烯属不饱和二羧酸的酸酐,其中单体M3a的比例基于单体M的总量通常不超过20重量%,尤其是10重量%。
单体M3进一步包括多烯属不饱和单体(M3b)。该类单体M3的比例基于单体M的总量通常不超过2重量%,尤其不超过0.5重量%。这些单体的实例是单烯属不饱和羧酸的乙烯基和烯丙基酯,如丙烯酸烯丙基酯和甲基丙烯酸烯丙基酯,二醇或多元醇的二-和多丙烯酸酯,如乙二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、丁二醇二丙烯酸酯、丁二醇二甲基丙烯酸酯、己二醇二丙烯酸酯、己二醇二甲基丙烯酸酯、三甘醇二丙烯酸酯、三甘醇三甲基丙烯酸酯、三(羟甲基)乙烷三丙烯酸酯和三(羟甲基)乙烷三甲基丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇三甲基丙烯酸酯,还有多元羧酸的烯丙基和甲代烯丙基酯,如马来酸二烯丙基酯、富马酸二烯丙基酯、邻苯二甲酸二烯丙基酯。典型的单体M3b还包括诸如二乙烯基苯、二乙烯基脲、二烯丙基脲、氰脲酸三烯丙基酯、N,N'-二乙烯基-和N,N’-二烯丙基咪唑烷-2-酮以及亚甲基二丙烯酰胺和亚甲基二甲基丙烯酰胺的化合物。
对本发明的制剂而言,还优选数均分子量Mn为1000-500000道尔顿,常常为1500-100000道尔顿,尤其是2000-50000道尔顿,特别是5000-20000道尔顿的共聚物CP。通常而言,重均分子量为2000-1000000道尔顿,常常为3000-200000道尔顿,特别是4000-100000道尔顿,尤其是10000-50000道尔顿。比例Mw/Mn通常为1.1∶1-10∶1,尤其是1.2∶1-5∶1。聚合物的摩尔质量Mw和Mn以及非均匀性通过尺寸排阻色谱法(=凝胶渗透色谱法或短GPC)测定。可以将市售聚甲基丙烯酸甲酯(PMMA)校正套装用作校正材料。
通常而言,本发明制剂中所包含的共聚物所具有的玻璃化转变温度Tg为-80℃至160℃,通常为-40℃至+100℃。这里的玻璃化转变温度Tg应理解为指根据ASTM D 3418-82由差示热分析(DSC)测定的“中点温度”(参见Ullmann’s Encyclopedia of Industrial Chemistry,第5版,第A 21卷,VCH Weinheim 1992,第169页以及Zosel,Farbe und Lack 82(1976),第125-134页,还参见DIN 53765)。
就此而言,已经发现有用的是借助Fox方程使用构成该聚合物的单体M各自的均聚物的玻璃化转变温度估算共聚物CP的玻璃化转变温度Tg(T.G.Fox,Bull.Am.Phys.Soc.(Ser.II)1,123[1956]和UllmannsEnzyklopdie der technischen Chemie[Ullmann工业化学大全],Weinheim(1980),第17-18页)。后者例如由Ullmann’s Encyclopedia ofIndustrial Chemistry,VCH,Weinheim,第A 21卷(1992),第169页或J.Brandrup,E.H.Immergut,Polymer Handbook,第3版,J.Wiley,New York 1989已知。
本发明制剂中所包含的某些共聚物CP由PCT/EP 04/011797已知,或者它们可以通过单体M的自由基聚合由常规方法制备。聚合可以通过自由基聚合或受控自由基聚合方法进行。聚合可以使用一种或多种引发剂进行且可以溶液聚合、乳液聚合、悬浮聚合或沉淀聚合进行或直接进行。聚合可以作为分批反应或以半连续或连续操作进行。
反应时间通常为1-12小时。反应可以进行的温度范围通常为20-200℃,优选40-120℃。聚合压力不太重要且可以为大气压力或稍微降低的压力,例如>800毫巴,或为超计大气压力,例如至多10巴,还可以使用更高或更低的压力。
适于自由基聚合的引发剂是常规的自由基形成物质。优选选自偶氮化合物、过氧化物或氢过氧化物的引发剂。可以提到的实例是过氧化乙酰、过氧化苯甲酰、过氧化月桂酰、过氧化异丁酸叔丁基酯、过氧化己酰、氢过氧化枯烯、2,2’-偶氮二异丁腈、2,2’-偶氮二(2-甲基丁腈)、2,2’-偶氮二[2-甲基-N-(2-羟基乙基)丙酰胺]、1,1’-偶氮二(1-环己烷甲腈)、2,2’-偶氮二(2,4-二甲基戊腈)、2,2’-偶氮二(N,N’-二亚甲基异丁脒)。特别优选偶氮二异丁腈(AIBN)。引发剂的用量基于单体M的量通常为0.02-5重量%,尤其是0.05-3重量%。引发剂的最佳量当然取决于所用引发剂体系且可以由本领域熟练技术人员以标准试验确定。可以首先将部分或所有引发剂加入反应容器中。优选在聚合过程中将主要量的引发剂,尤其是至少80%,例如80-100%的引发剂加入聚合反应器中。
当然,共聚物CP的分子量可以通过加入少量,例如基于待聚合单体M为0.01-5重量%的调节剂而调节。合适的调节剂尤其是有机硫代化合物,例如巯基醇类,如巯基乙醇,巯基羧酸,如巯基乙酸、巯基丙酸,烷基硫醇,如十二烷基硫醇,此外还有烯丙基醇和醛。
共聚物CP尤其通过在溶剂中的自由基溶液聚合而制备。溶剂的实例是水,醇类,如甲醇、乙醇、正丙醇和异丙醇,偶极非质子溶剂,例如N-烷基内酰胺,如N-甲基吡咯烷酮(NMP)、N-乙基吡咯烷酮,此外还有二甲亚砜(DMSO),脂族羧酸的N,N-二烷基酰胺,如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺,此外还有可以被卤代的芳族、脂族和环脂族烃类,如己烷、氯苯、甲苯或苯。优选的溶剂是异丙醇、甲醇、甲苯、DMF、NMP、DMSO和己烷;特别优选DMF。
本发明制剂可以配制成固体形式或液体形式。取决于实施方案,本发明制剂还可以包含常用于作物保护组合物或材料保护组合物中的助剂和/或载体。助剂尤其包括常规表面活性物质以及常用于作物保护和材料保护中的其他添加剂和载体,这些化合物可以是固体或液体。表面活性物质尤其包括表面活性剂,特别是具有润湿剂性能的那些。其他助剂(添加剂)尤其包括增稠剂、消泡剂、防腐剂、防冻剂、稳定剂、抗结块剂或粉末流动助剂和缓冲剂。
原则上合适的常规表面活性物质是阴离子、非离子和两性表面活性剂,包括聚合物表面活性剂,并且表面活性剂的分子量通常不超过2000道尔顿,尤其1000道尔顿(数均)。
阴离子表面活性剂例如包括羧酸盐,尤其是脂肪酸的碱金属、碱土金属和铵盐,例如硬脂酸钾,它们通常也被称为皂;酰基谷氨酸盐;肌氨酸盐,例如月桂酰肌氨酸钠;牛磺酸盐;甲基纤维素;烷基磷酸酯,尤其是单-和二磷酸的烷基酯;硫酸盐,尤其是烷基硫酸盐和烷基醚硫酸盐;磺酸盐,此外还有烷基磺酸盐和烷基芳基磺酸盐,尤其是芳基磺酸和烷基取代的芳基磺酸的碱金属、碱土金属和铵盐,烷基苯磺酸,如木素和苯酚磺酸,萘磺酸和二丁基萘磺酸,或十二烷基苯磺酸盐,烷基萘磺酸盐,烷基甲基酯磺酸盐,磺化萘及其衍生物与甲醛的缩合物,萘磺酸、苯酚-和/或苯酚磺酸与甲醛或与甲醛和脲的缩合物,磺基琥珀酸单-或二烷基酯;以及蛋白质水解物和木素亚硫酸盐废液,上述磺酸有利地以其中性或合适的话碱性盐形式使用。
非离子表面活性剂例如包括:
-烷氧基化程度通常为2-100,尤其是3-50的脂肪醇烷氧基化物和羰基合成醇烷氧基化物,尤其是乙氧基化物和丙氧基化物,例如C8-C30链烷醇或链(二)烯醇的烷氧基化物,如异十三烷醇、月桂醇、油醇或硬脂醇的烷氧基化物,以及它们的C1-C4烷基醚和C1-C4烷基酯,例如它们的乙酸酯;
-烷氧基化动物和/或植物脂肪和/或油,例如玉米油乙氧基化物、蓖麻油乙氧基化物、牛脂乙氧基化物,
-甘油酯,如甘油单硬脂酸酯,
-烷基酚烷氧基化物,如乙氧基化异辛基酚、辛基酚或壬基酚,三丁基酚聚氧乙烯醚,
-脂肪胺烷氧基化物、脂肪酸酰胺烷氧基化物和脂肪酸二乙醇酰胺烷氧基化物,尤其是其乙氧基化物,
-糖类表面活性剂,山梨醇酯,如脱水山梨糖醇脂肪酸酯(脱水山梨糖醇单油酸酯、脱水山梨糖醇三硬脂酸酯),聚氧乙烯脱水山梨醇脂肪酸酯,烷基聚苷,N-烷基葡糖酰胺,
-烷基甲基亚砜,
-烷基二甲基膦氧化物,如十四烷基二甲基膦氧化物。
两性表面活性剂例如包括磺基甜菜碱、羧基甜菜碱和烷基二甲基胺氧化物,例如十四烷基二甲基胺氧化物。
在这里可以举例提到的其他表面活性剂是全氟表面活性剂,聚硅氧烷表面活性剂,磷脂,例如卵磷脂或化学改性的卵磷脂,氨基酸表面活性剂,例如N-月桂酰谷氨酸盐。
除非另有指明,上述表面活性剂的烷基链是通常具有6-30个,尤其是8-20个碳原子的线性或支化基团。
在一个实施方案中,本发明的含水制剂包含不超过10重量%,优选不超过5重量%,尤其不超过3重量%,例如0.01-5重量%或0.1-3重量%的常规表面活性物质,在每种情况下基于活性化合物和共聚物CP的总量。
然而,取决于应用,可能有利的是用表面活性物质配制本发明的活性化合物制剂。此时,常规表面活性物质的比例基于活性化合物和共聚物CP的总量常常为0.1-60重量%,尤其是0.5-50重量%,或者基于配制的制剂的总重量为0.1-60重量%,特别是0.5-50重量%,尤其是0.5-30重量%。
尽管本发明制剂的优点之一是它们的挥发性有机化合物含量低这一事实,但对于某些应用而言,可能有利的是将本发明制剂与有机溶剂、油和脂肪,优选环境友好或生物相容的溶剂或油和脂肪,例如上述水溶混性溶剂或与水的溶混性仅非常有限或不与水溶混的溶剂、油或脂肪混合。这些例如包括:
-石蜡油,芳族烃类以及芳族烃类的混合物,例如二甲苯类,Solvesso 100、150或200等,
-酚类和烷基酚类,例如苯酚、氢醌、壬基酚等,
-具有超过4个碳原子的酮类,如环己酮、异佛尔酮、isopherone、苯乙酮、乙酰萘,
-具有超过4个碳原子的醇类,如乙酰化羊毛脂醇、鲸蜡醇、1-癸醇、1-庚醇、1-己醇、异十八烷醇、异丙醇、油醇、苄醇,
-羧酸酯类,例如己二酸二烷基酯,如己二酸二(2-乙基己基)酯,邻苯二甲酸二烷基酯,如邻苯二甲酸二(2-乙基己基)酯,乙酸烷基酯(还有支化烷基),如乙酸乙酯和乙酰乙酸乙酯,硬脂酸酯,如硬脂酸丁酯、甘油单硬脂酸酯,柠檬酸酯,如柠檬酸乙酰三丁酯,此外还有辛酸鲸蜡基酯、油酸甲酯、对羟基苯甲酸甲酯、十四烷酸甲酯、对羟基苯甲酸丙酯、苯甲酸甲酯,乳酸酯,如乳酸异丙酯、乳酸丁酯和乳酸2-乙基己基酯,
-植物油,如棕榈油、菜子油、蓖麻油及其衍生物,如氧化蓖麻油,椰子油、鳕鱼肝油、玉米油、大豆油、亚麻子油、橄榄油、花生油、红花油、芝麻子油、圆柚油、罗勒油、杏油、姜油、香叶油、橙油、迷迭香油、澳洲坚果油、洋葱油、橘子油、松油、向日葵油,
-氢化植物油,如氢化棕榈油、氢化菜子油、氢化大豆油,
-动物油,如猪脂油、鱼油,
-中链至长链脂肪酸的二烷基酰胺,例如hallcomide,以及-植物油酯,如菜子油甲基酯。
合适的增稠剂是赋予含水制剂以假塑性流动行为,即静止时的高粘度和搅拌状态下的低粘度的化合物。就此而言例如可以提到多糖,如黄原胶(Kelco的Kelzan;Rhone Poulenc的Rhodopol23或R.T.Vanderbilt的Veegum),还有无机片状矿物,如Attaclay(来自Engelhardt),优选黄原胶。
适合于本发明分散体的消泡剂例如为聚硅氧烷乳液(例如Wacker的SilikonSRE或Rhodia的Rhodorsil),长链醇,脂肪酸,有机芴化合物及其混合物。
可以加入杀菌剂以稳定本发明制剂而免受微生物侵袭。这些通常为异噻唑啉酮化合物,例如1,2-苯并异噻唑啉-3-酮、5-氯-2-甲基异噻唑啉-3-酮、2-甲基异噻唑啉-3-酮或2-辛基异噻唑啉-3-酮,它们例如可以商品名Proxel从Arch Chemical Inc.购得,以商品名ActicideRS从Thor Chemie购得并以商品名KathonMK从Rohm&Haas购得。
合适的防冻剂是有机多元醇,例如乙二醇、丙二醇或甘油。它们通常基于含水活性化合物制剂的总重量以不超过20重量%,例如1-20重量%,尤其是2-10重量%的量用于含水配制剂中。
合适的话,本发明的活性化合物制剂可以基于所生产的制剂总量包含1-5重量%的缓冲剂,以调节该制剂或稀释施用形式的pH,所用缓冲剂的量和类型取决于活性化合物和聚合物CP的化学性能和量。缓冲剂的实例是弱无机或有机酸,如磷酸、硼酸、乙酸、丙酸、柠檬酸、富马酸、酒石酸、草酸和琥珀酸的碱金属盐。
粉末流动助剂的实例尤其是硅酸,特别是热解硅酸和沉淀硅酸,还有碳酸钙和硬脂酸镁。若存在的话,粉末流动助剂的量基于该组合物的总重量通常为至多5重量%,尤其是至多2重量%,例如0.1-5重量%或0.2-2重量%。
合适的载体原则上是所有常用于作物保护或材料保护配制剂,尤其是杀真菌剂配制剂中并且通常呈化学惰性的液体和固体物质。液体载体尤其是水和水与有机水溶混性溶剂的混合物。固体载体例如为硅酸盐和铝硅酸盐,包括红玄武土、黄土、粘土和矾土,例如层状硅酸盐和架状硅酸盐,如蒙脱石、锂蒙脱石、皂石、贝得石、锌蒙脱石、膨润土、滑石、高岭土、硅镁土,此外还有无定形硅酸盐和硅酸,如硅胶、硅藻土,例如呈硅藻土形式,沉淀硅酸,合成硅酸盐和铝硅酸盐,如沸石,此外还有石灰石、石灰、白垩、白云石、硫酸钙和硫酸镁,氧化镁,磨碎的合成矿物,肥料,如硫酸铵、磷酸铵、硝酸铵、脲和植物来源的产品,如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其他固体载体。固体载体优选为水溶性或水分散性的。
本发明的另一优选实施方案涉及固体形式的制剂。活性化合物(活性化合物1+活性化合物2)的总量基于该制剂的总重量通常为5-90重量%,尤其是10-70重量%,特别是15-60重量%。共聚物CP的比例基于该制剂的总重量通常为5-95重量%,尤其是10-90重量%,特别是20-85重量%。助剂和固体载体的比例可以为本发明固体制剂的至多90重量%,尤其是至多80重量%,特别是至多65重量%。应理解的是在固体配制剂中,不同于活性化合物1和2的液体组分,尤其是液体溶剂组分的比例通常不超过配制剂的20重量%,特别是不超过10重量%,尤其不超过1重量%。
固体制剂可以各种宏观形式存在。可以提到的宏观形式的实例是例如通过喷雾干燥或冻干液体配制剂而得到的粉末、研磨材料、颗粒、附聚体或膜。优选粉末。
固体制剂的第一实施方案是基本不包含任何固体载体且基本,即至少95%,尤其是至少99%由活性化合物1和2、聚合物CP和合适的话,固体,优选水溶性助剂组成的那些。在这些配制剂中,活性化合物(活性化合物1+活性化合物2)的总量基于该制剂的总重量通常为5-90重量%,尤其是10-70重量%,特别是15-60重量%。共聚物CP的比例基于不含固体载体的制剂的总重量通常为5-95重量%,尤其是10-90重量%,特别是20-85重量%。助剂的比例通常为本发明固体制剂的至多60重量%,尤其是至多80重量%,特别是至多65重量%。若固体制剂以粉末存在,则它们可包含上述量的粉末流动助剂,固体惰性载体的比例优选不超过5重量%,尤其不超过1重量%。
固体制剂的第二实施方案是除了活性化合物1和2、聚合物CP和合适的话,固体,优选水溶性助剂外包含至少一种固体载体的那些。在这些配制剂中,活性化合物(活性化合物1+活性化合物2)的总量基于该制剂的总重量通常为5-80重量%,尤其是10-60重量%,特别是15-50重量%。共聚物CP的比例基于不含固体载体的制剂的总重量通常为5-85重量%,尤其是10-70重量%,特别是20-65重量%。载体材料的比例基于该组合物的总重量通常为10-90重量%,20-80重量%,尤其是30-65重量%。助剂的比例可以为本发明固体制剂的至多80重量%,尤其是至多70重量%,特别是至多55重量%。若固体制剂以粉末存在,则它们可以包含上述量的粉末流动助剂。优选的载体材料是硅酸盐,例如层状硅酸盐,包括粘土,如蒙脱石、锂蒙脱石、皂石、贝得石、锌蒙脱石、膨润土、滑石,此外还有无定形硅酸盐和硅酸,如硅胶、硅藻土,例如呈硅藻土形式,沉淀硅酸,合成硅酸盐,如沸石。
在另一实施方案中,本发明制剂为液体制剂或尤其是含水制剂。除了组分活性化合物1、活性化合物2和共聚物CP外,该类制剂还包含液体载体,尤其是水或水与水溶混性有机溶剂的混合物,其中有机溶剂的比例基于该组合物的总重量优选不超过20重量%。
水溶混性有机溶剂的实例是C3-C4酮类,如丙酮和甲基乙基酮,环醚,如二烷和四氢呋喃,C1-C4链烷醇,如甲醇、乙醇、正丙醇、异丙醇、正丁醇、叔丁醇,多元醇及其单-和二甲基醚,如乙二醇、丙二醇、乙二醇单甲基醚、二甘醇、二甘醇单甲基醚、二甘醇二甲基醚、甘油,此外还有C2-C3腈,如乙腈和丙腈,二甲亚砜、二甲基甲酰胺、甲酰胺、乙酰胺、二甲基乙酰胺、丁内酯、2-吡咯烷酮和N-甲基吡咯烷酮。
在液体,尤其是含水浓缩物(液体配制剂)中存在的活性化合物(活性化合物1+活性化合物2)的总量基于该制剂的总重量通常为1-50重量%,特别是5-40重量%,尤其是7-35重量%。共聚物CP的量基于该制剂的总重量通常为3-50重量%,特别是5-45重量%,尤其是10-40重量%。助剂的比例可以为本发明液体制剂的至多30重量%,尤其是至多20重量%,特别是至多10重量%。液体制剂的典型助剂例如为增稠剂、消泡剂、防腐剂、防冻剂、生物杀伤剂、pH调节剂和表面活性物质。固体含量通常为5-70重量%,尤其是10-60重量%,特别是20-55重量%。水不溶混性挥发性组分的比例基于含水液体配制剂的总重量有利地不超过5重量%,尤其不超过1重量%。
在含水制剂中,活性化合物1和2以及共聚物CP以细碎分布形式存在于水相中。通过光散射测定的在浓缩物中的平均粒度通常小于1μm,尤其小于500nm,特别小于300nm。
水相应理解为纯水或包含溶解的添加剂如缓冲剂体系或盐或其他添加剂如水溶混性溶剂的水。水相的pH通常为2-13,优选3-12,特别优选4-10。
通常而言,含水配制剂包含至少一种上述防冻剂,合适的话一种或多种上述生物杀伤剂,合适的话一种或多种上述增稠剂,合适的话一种或多种上述用于调节pH的试剂(缓冲剂),合适的话一种或多种上述消泡剂以及合适的话一种或多种上述表面活性物质。
本发明进一步涉及一种制备上述制剂的方法,下文称为方法1。通常而言,该方法包括使用常规方法充分混合存在于本发明制剂中的组分。
在优选实施方案中,通过包括如下步骤的方法实现充分混合:
i)提供活性化合物1、共聚物CP和至少一种其他活性化合物2在有机溶剂中的溶液,然后
ii)基本或完全除去有机溶剂。
若作为制备的结果共聚物CP已存在于有机溶剂中,则优选将该溶液用于与活性化合物或活性化合物溶液混合。
在方法1的第一步中,制备共聚物和至少一种其他活性化合物在合适的有机溶剂中的溶液。为此,通常将共聚物CP在第一有机溶剂中的第一溶液与活性化合物1和2在有机溶剂中的一种或两种单独溶液混合,其中这些溶液可能已经包含其他助剂和添加剂。还可以在后面的时间点加入助剂和添加剂。用于制备溶液的溶剂可以相同或不同;通常而言,选择相互溶混的溶剂。若共聚物CP的合成在适用于制备本发明配制剂的方法中的溶剂中进行,则可能不必制备共聚物CP的溶液。
适于该目的的有机溶剂的实例是C1-C6烷基醇,如甲醇、乙醇、丙醇、异丙醇、1-丁醇、2-丁醇、叔丁醇,脂族C1-C4羧酸与C1-C4链烷醇的酯,如乙酸乙酯、乙酸丁酯,优选具有3-6个碳原子的酮类,如丙酮、甲基乙基酮、甲基异丙基酮、甲基异丁基酮,缩醛类,二-C1-C4烷基醚,如乙醚、甲基叔丁基醚,环醚,如四氢呋喃,脂族C1-C4羧酸,如甲酸、乙酸、丙酸,N-取代或N,N-二取代的C1-C4羧酰胺,如乙酰胺、二甲基甲酰胺(DMF)和二甲基丙酰胺,内酰胺,如N-甲基吡咯烷酮,内酯,如丁内酯,脂族和芳族氯代烃,如二氯甲烷、氯仿、1,2-二氯乙烷或氯苯,以及上述溶剂的混合物。优选的有机溶剂是甲醇、乙醇、异丙醇、二甲基甲酰胺、N-甲基吡咯烷酮、二氯甲烷、氯仿、1,2-二氯乙烷、氯苯、丙酮、甲基乙基酮、甲基异丙基酮、甲基异丁基酮、四氢呋喃以及这些溶剂的混合物。特别优选的溶剂是甲醇、乙醇、异丙醇、二甲基甲酰胺和四氢呋喃及其混合物。
在第二步骤中,通过合适的方法以常规方式非常显著地除去溶剂。常用于除去溶剂的方法例如为喷雾干燥,减压蒸发,冻干,在大气压力以及合适的话在升高的温度下蒸发。适于干燥的方法进一步包括冷冻干燥或在流化床干燥器中干燥。这以固体形式得到本发明的活性化合物配制剂。
以此方式通常得到固体、粘稠或凝胶状组合物。若在除去溶剂之后得到固体,则可以本身已知的方式且取决于干燥条件制备细碎粉末或粗碎颗粒,它们可以没有任何问题且粒度不显著增加地分散或溶解于水中。还可以制备粗碎固体并将其研磨至所需粒度。
为了制备包含载体的固体配制剂,例如还可以采用如下程序,其中:
i)提供活性化合物1、共聚物CP、至少一种其他活性化合物2以及合适的话助剂在一种或多种不同有机溶剂中的一种或多种单独溶液,
ii)将这些溶液与载体混合或施用于载体上,和
iii)基本或完全除去有机溶剂。
若在不使用载体时得到粘稠或凝胶状产品,则下文称为方法2的该方法特别合适。
在方法2中,有利地通过喷雾方法,例如通过喷雾干燥或喷雾造粒方法将溶液施用于载体上,其中溶剂同时被蒸发。助剂也可以该方式施用于载体或者可以在后面的时间点加入。
对于活性化合物1和2、共聚物CP和助剂的溶液,原则上讲上面对方法1所述的那些类似地适用。
通常而言,本发明含水制剂的制备包括将活性化合物1和2、共聚物CP和任何助剂掺入含水分散介质中。该方法例如可以包括如下步骤:
i)提供包含活性化合物1和2、共聚物CP和合适的话部分或所有助剂在优选与水溶混的有机溶剂中的溶液,上述组分的熔体或上述组分的粉末,
ii)将该溶液、熔体或粉末掺入含水分散介质中,和
iii)若存在的话,基本或完全除去有机溶剂。
为了制备本发明的含水制剂,将在步骤i)中得到的溶液或熔体或粉末分散于水或含水介质中。含水介质应理解为指水、表面活性物质的水溶液和水与水溶混性有机溶剂的混合物,其中该类溶剂的比例基于水和溶剂的总量通常不超过20体积%。
分散通常通过施加剪切力,例如通过在高频率和高振幅下振摇或通过高频搅拌、通过涡轮搅动或通过使用混合室而进行。分散可以连续或分批进行。优选连续分散。合适的话,分散可以在升高的温度和/或升高的压力下进行。
用于制备溶液的有机溶剂优选与水溶混。就此而言,与水溶混是指在混合条件下有机溶剂没有相分离地与水溶混至少10重量%,优选15重量%,特别优选20重量%。水溶混性有机溶剂的实例是上述那些,尤其是环醚,如四氢呋喃。
若已经将活性化合物1和2以及共聚物CP的溶液分散于水中,则此时基本或完全除去有机溶剂。这通常通过蒸馏进行,其中通常连续置换已经蒸除的水。
在另一同样优选的方法中,本发明含水制剂的制备包括下列步骤:
i)提供包含共聚物CP的水溶液,
ii)提供在一种或多种水溶混性有机溶剂中包含活性化合物1和至少一种其他活性化合物2的一种或两种单独溶液,
iii)将共聚物CP的水溶液与活性化合物1和2的溶液混合,和
iv)基本或完全除去有机溶剂。
在第一步中,将共聚物CP和合适的话其他添加剂溶于含水溶剂体系中。若制备已经提供了共聚物的水溶液,则优选将该水溶液用于与活性化合物溶液混合。此外,将活性化合物1和活性化合物2溶于水溶混性溶剂中,合适的话加入其他助剂。然后将共聚物CP的水溶液与氧唑菌和活性化合物2的溶液混合。
混合有利地在输入能量下进行,例如通过施加剪切力、通过在高频率和高振幅下振摇或通过在高频率下搅拌、通过涡轮搅动或通过使用混合室。混合可以连续或分批进行。优选连续混合。如上所述,可以常规方式除去以此方式得到的分散体的溶剂。
本发明的制剂的特征首先在于在用水稀释时确保分散的活性化合物相的极精细分布这一事实,其中分散的活性化合物相的平均粒度位于上述范围内。甚至在长期储存和/或在升高的温度下储存时,本发明的活性化合物制剂不丧失其性能。为此不要求使用其他表面活性化合物。此外,本发明制剂可以配制成低溶剂制剂(溶剂含量<5重量%)或无溶剂制剂(溶剂含量<1重量%,尤其<0.5重量%)。甚至在升高的温度和高度波动的温度下,该制剂可以不发生任何分离地储存几个月的较长时间。此外,不发生象某些康唑杀真菌剂的配制剂,尤其是氧唑菌配制剂有时可能发生的结晶现象。
本发明制剂特别适于防治病原性真菌且在这一方面至少等于并且通常优于活性化合物1和2的常规配制剂。本发明制剂对宽范围的植物病原性真菌,尤其是选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)和担子菌纲(Basidiomycetes)的真菌高度有效。
它们对在各种栽培植物如小麦、黑麦、大麦、燕麦、稻、玉米、禾草、香蕉、棉花、大豆、咖啡、甘蔗、葡萄藤、水果、观赏植物以及蔬菜如黄瓜、豆类、西红柿、土豆和葫芦科植物以及这些植物的种子中防治大量真菌尤其重要。
它们尤其适于防治下列植物病害:
●蔬菜和水果上的链格孢(Alternaria)属,
●禾谷类、稻和草坪中的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属,
●禾谷类中的禾白粉菌(Blumeria graminis)(白粉病),
●草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),
●葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),
●各种植物上的镰孢霉(Fusarium)属和轮枝孢(Verticillium)属,
●禾谷类、香蕉和花生上的球腔菌(Mycosphaerella)属,
●土豆和西红柿上的致病疫霉(Phytophthora infestans),
●葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
●苹果上的苹果白粉病菌(Podosphaera leucotricha),
●小麦和大麦上的小麦基腐病菌(Pseudocercosporella herpotrichoides),
●啤酒花和黄瓜上的假霜霉(Pseudoperonospora)属,
●禾谷类上的柄锈菌(Puccinia)属,
●稻上的稻瘟病菌(Pyricularia oryzae),
●棉花、稻和草坪上的丝核菌(Rhizoctonia)属,
●小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonosporanodorum),
●葡萄藤上的葡萄钩丝壳(Uncinula necator),
●禾谷类和甘蔗上的黑粉菌(Ustilago)属,以及
●苹果和梨上的黑星菌(Venturia)属(黑星病)。
本发明制剂还适于防治有害真菌如拟青霉(Paecilomyces variotii)以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。
制剂通常通过用包含杀真菌有效量的活性化合物1和2的本发明制剂的稀释含水制剂处理真菌或需要防止真菌侵袭的植物、种子、材料或土壤而施用。施用可以在材料、植物或种子被真菌侵染之前和之后进行。
含水制剂中的活性化合物浓度可以在较宽范围内变化。通常而言,它们为0.0001-1%,优选0.0005-0.1%。
当用于作物保护时,施用率取决于所需效果种类为0.01-2.0kg活性化合物/公顷。
在种子处理中,活性化合物的通常用量为1-1000g/100kg种子,优选1-200g/100kg,尤其是5-100g/100kg。
当用于保护材料或储存产品时,活性化合物的施用量取决于施用区域的种类和所需效果。在材料保护中的通常施用量例如为每立方米被处理材料0.001g-2kg,优选0.005g-1kg活性化合物。
下列实施例用于说明本发明而不应理解为限制本发明。
分析:
玻璃化转变温度使用购自Mettler的DSC设备DSC30以10K/min的加热速率测定。
分子量通过凝胶渗透色谱法(仪器为Agilent的“Series 1100”)测定,该方法使用来自PL的RI检测器和5μ混合-D柱在30℃(柱温)下进行。所用移动相为二甲基甲酰胺,其包含0.5%溴化锂。流速为1ml/min。校正使用聚甲基丙烯酸甲酯校正套装进行。
共聚物CP的制备
制备实施例1:共聚物CP1
首先将250g DMF加入反应容器中并加热到90c。在3小时内在相同温度下平行加入由49.5g 2-丙烯酰胺基-2-甲基丙烷磺酸、96.1g丙烯酸2-羟基乙基酯、145.6g丙烯酸正丁基酯和148.5g DMF组成的进料1和由8.74gAIBN和301.5g DMF组成的进料2。在加料结束之后,将该混合物在95℃下再聚合2小时。
制备实施例2:共聚物CP2
首先将300g DMF加入反应容器中并加热到90℃。在3小时内在相同温度下平行加入由36.0g 2-丙烯酰胺基-2-甲基丙烷磺酸、184.0g丙烯酸2-羟基乙基酯、180.0g丙烯酸正丁基酯和148.5g DMF组成的进料1和由12.0gAIBN和120g DMF组成的进料2。在加料结束之后,将该混合物在95℃下再聚合2小时。
制备实施例3:共聚物CP3
首先使用惰性气体将300g DMF加入反应容器中并加热到90℃。在3小时内在相同温度下平行加入由36.0g 2-丙烯酰胺基-2-甲基丙烷磺酸、192.0g丙烯酸2-羟基乙基酯、172.0g丙烯酸正丁基酯和148.5g DMF组成的进料1和由12.0g AIBN和120g DMF组成的进料2。在加料结束之后,将该混合物在95℃下再聚合2小时。
制备实施例4-6
通用制备程序
在来自Chemspeed的合成反应器AutoPlant A100中首先每个反应器加入15ml DMF并加热到95℃。在搅拌并维持温度下分别在180分钟和195分钟内平行加入进料1和进料2,其中进料2与进料1在相同时间开始。在所有进料结束之后,再将该混合物在95℃下后聚合60分钟。
制备实施例4:共聚物CP4
进料1:包含10.5g甲基丙烯酸甲酯、3.5g丙烯酸月桂基酯和7.0g 2-丙烯酰胺基-2-甲基丙烷磺酸的混合物,在DMF中溶解成49ml。
进料2:0.63g 2,2’-偶氮二(2-甲基丙腈),在DMF中溶解成6ml。
制备实施例5:共聚物CP5
进料1:包含10.5g丙烯酸正丁基酯、7.0g丙烯酸2-羟基乙基酯和3.5g2-丙烯酰胺基-2-甲基丙烷磺酸的混合物,在DMF中溶解成49ml。
进料2:0.63g 2,2’-偶氮二(2-甲基丙腈),在DMF中溶解成6ml。
制备实施例6:共聚物CP6
进料1:包含17.5g丙烯酸甲酯和3.5g 2-丙烯酰胺基-2-甲基丙烷磺酸的混合物,在DMF中溶解成49ml。
进料2:0.63g 2,2’-偶氮二(2-甲基丙腈),在DMF中溶解成6ml。
制备实施例7-9
通用制备程序:
在来自Chemspeed的合成反应器AcceleratorTM SLT100中,对每个反应容器将0.21ml引发剂溶液2加入6.72ml单体溶液1中。然后在振摇下将该混合物在95℃下加热4小时,然后加入另外0.07ml引发剂溶液2并在95℃下聚合2小时。
制备实施例7:CP7
单体溶液1:包含150mg甲基丙烯酸甲酯、450mg丙烯酸2-苯氧基乙基酯和300mg 2-丙烯酰胺基-2-甲基丙烷磺酸的混合物,在DMF溶解成8.64ml。
引发剂溶液2:100mg 2,2’-偶氮二(2-甲基丙腈),在DMF中溶解成1.00ml。
制备实施例8:CP8
单体溶液1:包含300甲基丙烯酸羟丙基酯、300mg苯乙烯和300mg2-丙烯酰胺基-2-甲基丙烷磺酸的混合物,在DMF溶解成8.64ml。
引发剂溶液2:100mg 2,2’-偶氮二(2-甲基丙腈),在DMF中溶解成1.00ml。
制备实施例9:CP9
单体溶液1:包含450mg丙烯酸甲酯、300mg 1-乙烯基-2-吡咯烷酮和150mg 2-丙烯酰胺基-2-甲基丙烷磺酸的混合物,在DMF溶解成8.64ml。
引发剂溶液2:100mg 2,2’-偶氮二(2-甲基丙腈),在DMF中溶解成1.00ml。
共聚物CP1-CP4的分子量和玻璃化温度列于表1中:
表1:
共聚物 | Mn | Mw | Tg[℃] |
CP1 | 5700 | 11000 | 16 |
CP2 | 7600 | 15900 | -6 |
CP3 | 7800 | 16800 | -4 |
CP4 | 12437 | 21853 | n.d. |
n.d.未测定
本发明制剂Z1、Z2、Z3、Z4和Z5的制备:
固体配制剂的通用制备程序
将10g氧唑菌和唑菌胺酯(在Z1、Z2和Z3的情况下重量比为5∶7;在Z5的情况下重量比为1∶1)或氧唑菌和环戊唑菌(在Z4的情况下重量比为1∶1)的活性化合物混合物溶于30g共聚物CP和70g DMF的溶液中。在80℃的温度下减压除去溶剂,得到没有结晶组分的固体均相材料。
在对比试验VZ1、VZ2、VZ3和VZ4中,代替活性化合物混合物,将10g纯氧唑菌在上述条件下配制。这得到各自具有结晶组分的固体材料。
表2:固体活性化合物配制剂的制备
制剂 | 共聚物 | 活性化合物类型 | 活性化合物/共聚物[g/g]1) |
Z1 | CP1 | 氧唑菌/唑菌胺酯5∶71) | 1∶3 |
Z2 | CP2 | 氧唑菌/唑菌胺酯5∶71) | 1∶3 |
Z3 | CP3 | 氧唑菌/唑菌胺酯5∶71) | 1∶3 |
Z4 | CP4 | 氧唑菌/环戊唑菌1∶11) | 1∶3 |
Z5 | CP4 | 环戊唑菌/唑菌胺酯1∶11) | 1∶3 |
VZ1* | CP1 | 氧唑菌 | 1∶3 |
VZ2* | CP2 | 氧唑菌 | 1∶3 |
VZ3* | CP3 | 氧唑菌 | 1∶3 |
VZ4* | CP4 | 氧唑菌 | 1∶3 |
*对比配制剂
1)重量比
在用水将制剂Z1、Z2、Z3、Z4和Z5稀释成活性化合物浓度为64ppm时,得到光学水清溶液。因此,所有样品的平均粒度小于100nm。相反,在稀释样品VZ1-VZ4时,观察到固体的分离。
为了测定储存稳定性,将制剂Z1、Z2、Z3、Z4和Z5的样品在-10℃、室温或55℃下储存5个月。在所有样品中没有形成结晶材料。在这段时间之后,所有样品可以用水稀释而得到光学水清溶液。
施用试验
杀真菌作用的检测
将所述活性化合物制剂制备成活性化合物浓度为64ppm的储备溶液,然后用水稀释至下述活性化合物浓度(表3)。
将栽培品种为“Kanzler”的盆栽小麦秧苗的叶子用小麦叶锈病菌(小麦隐匿柄锈菌(Puccinia recondita))的孢子悬浮液接种。然后将盆置于高大气湿度(90-95%)和20-22℃的室中24小时。在这段时间内孢子萌发并且芽管穿透到叶组织中。第二天将侵染的植物用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。该悬浮液如上所述制备。在喷雾涂层干燥之后,将试验植物在温室中于20-22℃的温度和65-70%的相对大气湿度下栽培7天。然后测定叶子上的锈病真菌发展程度。
生物试验的结果总结于表3中。结果表明在低施用率下,共聚物稳定的活性化合物混合物与市售产品相比具有更好的杀真菌活性。
表3:
侵染[%] | 侵染[%] | 侵染[%] | 侵染[%] | |
制剂:施用率[ppm] | Z1 | Z2 | Z3 | 常规悬浮乳液1) |
32 | 2 | 4 | 0 | 6 |
16 | 15 | 18 | 6 | 16 |
8 | 43 | 40 | 43 | 60 |
1)常规悬浮乳液的制备:
4.7重量%氧唑菌
12.5重量%唑菌胺酯
29.2重量%芳族溶剂
约12重量%脂肪醇乙氧基化物
约4重量%苯酚磺酸/甲醛缩合物钠盐
增稠剂
生物杀伤剂
在1升含水配制剂中
Claims (40)
1.一种制剂,包含至少两种不同作物保护剂的混合物,其中:
a)至少一种杀真菌活性化合物选自康唑(活性化合物1),和
b)至少一种其他作物保护剂(活性化合物2)在20℃下在水中的溶解度低于20g/l,
进一步包含
c)至少一种由烯属不饱和单体M构成的共聚物CP,其中单体M包含:
α)至少一种具有至少一个磺酸基团的单烯属不饱和单体M1,和
β)至少一种中性单烯属不饱和单体M2,
其中活性化合物1与至少一种其他作物保护剂2的比例为1∶10-10∶1。
2.根据权利要求1的制剂,其中活性化合物1为氧唑菌。
3.根据权利要求1或2的制剂,其中活性化合物2选自与活性化合物1不同的康唑杀真菌剂、嗜球果伞素类、吗啉杀真菌剂、螺茂胺、百菌清、苯菌酮和啶酰菌胺。
4.根据权利要求2或3的制剂,其中活性化合物1为氧唑菌且活性化合物2为唑菌胺酯。
5.根据权利要求2或3的制剂,其中活性化合物1为氧唑菌且活性化合物2选自丙氯灵、环唑醇、喹唑菌酮、己唑醇、环戊唑菌、戊菌唑、丙环唑、丙硫菌唑、戊唑醇和戊叉唑菌。
6.根据前述权利要求中任一项的制剂,其中在共聚物CP中,单体M1占构成共聚物CP的单体M的总量的1-90重量%。
8.根据前述权利要求中任一项的制剂,其中在共聚物CP中,单体M2包含至少一种在20℃下在水中的溶解度低于50g/l的单体M2a。
9.根据权利要求8的制剂,其中单体M2a占构成共聚物CP的单体M的总量的10-99重量%。
10.根据权利要求8或9的制剂,其中单体M2a选自乙烯基芳族单体,丙烯酸与C2-C20链烷醇、C4-C10环烷醇、苯基-C1-C4链烷醇和苯氧基-C1-C4链烷醇的酯以及甲基丙烯酸与C1-C20链烷醇、C4-C10环烷醇、苯基-C1-C4链烷醇和苯氧基-C1-C4链烷醇的酯。
11.根据权利要求8-10中任一项的制剂,其中在共聚物CP中,单体M2额外包含至少一种在20℃下在水中的溶解度高于50g/l的单体M2b。
12.根据权利要求11的制剂,其中单体M1+M2b的总量占构成共聚物CP的单体M的总量的10-90重量%。
13.根据权利要求11或12的制剂,其中单体M2b选自丙烯酸和甲基丙烯酸的羟基-C2-C4烷基酯、丙烯酰胺、甲基丙烯酰胺、丙烯腈、N-乙烯基内酰胺和丙烯酸甲酯。
14.根据权利要求8-13中任一项的制剂,其中单体M2a包括至少一种在20℃下在水中的溶解度为1-<50g/l的第一单体M2a(1)和至少一种在20℃下在水中的溶解度<1g/l的第二单体M2a(2)。
15.根据权利要求14的制剂,其中单体M2a(1)选自丙烯酸与C2-C4链烷醇的酯和甲基丙烯酸与C1-C4链烷醇的酯。
16.根据权利要求14或15的制剂,其中单体M2a(2)选自丙烯酸C6-C20烷基酯和甲基丙烯酸C6-C20烷基酯。
17.根据权利要求14-16中任一项的制剂,包含:
1-89重量%单体M1,
10-98重量%单体M2a(1),和
1-89重量%单体M2a(2),
所有以重量%的表述基于构成共聚物CP的单体M的总量。
18.根据前述权利要求中任一项的制剂,其中共聚物CP的数均分子量为1000-100000道尔顿。
19.根据前述权利要求中任一项的制剂,其基于活性化合物1和活性化合物2的总量包含10-1000重量%的共聚物CP。
20.根据前述权利要求中任一项的制剂,呈固体形式。
21.根据权利要求20的制剂,呈水分散性粉末形式或水分散性颗粒形式。
22.根据权利要求16的制剂,额外包含惰性细碎无机载体。
23.一种生产根据前述权利要求中任一项的制剂的方法,包括充分混合活性化合物1、共聚物CP和活性化合物2以及合适的话其他组分。
24.根据权利要求23的方法,其中混合包括下列步骤:
i)提供活性化合物1、共聚物CP和活性化合物2在有机溶剂中的溶液,和
ii)除去有机溶剂。
25.根据权利要求24的方法,额外包括将在步骤ii)中得到的材料或在步骤i)中得到的溶液分散于水中。
26.根据权利要求1-22中任一项的制剂在防治植物病原性真菌中的用途。
27.如权利要求1所定义的共聚物CP在生产活性化合物制剂中的用途,所述制剂包含:
a)至少一种选自康唑的杀真菌活性化合物(活性化合物1),和
b)至少一种在20℃下在水中的溶解度低于20g/l的其他作物保护剂(活性化合物2),
其中活性化合物1与活性化合物2的比例为10∶1-1∶10。
28.如权利要求1所定义的共聚物CP在稳定活性化合物混合物的水分散体中的用途,所述混合物包含:
a)至少一种选自康唑的杀真菌活性化合物(活性化合物1),和
b)至少一种在水中的溶解度低于20g/l的其他作物保护剂(活性化合物2),其中活性化合物1与活性化合物2的比例为10∶1-1∶10。
29.一种呈由至少三种不同的单烯属不饱和单体M构成的聚合物形式的共聚物CP,其以聚合单元形式包含:
α)至少一种具有至少一个磺酸基团的单烯属不饱和单体M1,
β1)至少一种在20℃下在水中的溶解度低于50g/l的中性单烯属不饱和单体M2a,和
β2)至少一种在20℃下在水中的溶解度高于50g/l的中性单烯属不饱和单体M2b。
30.根据权利要求29的共聚物CP,其中单体M1占构成共聚物CP的单体M的总量的1-80重量%。
31.根据权利要求29或30的共聚物CP,其中单体M2a占构成共聚物CP的单体M的总量的10-90重量%。
32.根据权利要求29-31中任一项的共聚物CP,其中单体M2a选自乙烯基芳族单体,丙烯酸与C2-C10链烷醇、C4-C10环烷醇、苯基-C1-C4链烷醇和苯氧基-C1-C4链烷醇的酯以及甲基丙烯酸与C1-C10链烷醇、C4-C10环烷醇、苯基-C1-C4链烷醇和苯氧基-C1-C4链烷醇的酯。
33.根据权利要求29-32中任一项的共聚物CP,其中单体M2b占构成共聚物CP的单体M的总量的5-89重量%。
34.根据权利要求29-33中任一项的共聚物CP,其中单体M2b选自丙烯酸和甲基丙烯酸的羟基-C2-C4烷基酯、丙烯酰胺、甲基丙烯酰胺、丙烯腈、N-乙烯基内酰胺和丙烯酸甲酯。
35.根据权利要求29-34中任一项的共聚物CP,其数均分子量为1000-100000道尔顿。
36.一种呈由至少三种不同的单烯属不饱和单体M构成的聚合物形式的共聚物CP,其以聚合单元形式包含:
α)至少一种具有至少一个磺酸基团的单烯属不饱和单体M1,
β3)至少一种在20℃下在水中的溶解度为1-<50g/l的单烯属不饱和单体M2a(1),和
β4)至少一种在20℃下在水中的溶解度低于1g/l的第二单体M2a(2)。
37.根据权利要求36的共聚物CP,其中单体M2a(1)选自丙烯酸与C2-C4链烷醇的酯和甲基丙烯酸与C1-C4链烷醇的酯。
38.根据权利要求36或37的共聚物CP,其中单体M2a(2)选自丙烯酸C6-C20烷基酯和甲基丙烯酸C6-C20烷基酯。
39.根据权利要求36-38中任一项的共聚物CP,包含:
1-89重量%单体M1,
10-98重量%单体M2a(1),和
1-89重量%单体M2a(2),
所有以重量%的表述基于构成共聚物CP的单体M的总量。
40.根据权利要求36-39中任一项的共聚物CP,其数均分子量为1000-100000道尔顿。
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