CN101170902B - 含水杀虫剂组合物及其在保护含木质纤维素的材料中的用途 - Google Patents
含水杀虫剂组合物及其在保护含木质纤维素的材料中的用途 Download PDFInfo
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- CN101170902B CN101170902B CN2006800157177A CN200680015717A CN101170902B CN 101170902 B CN101170902 B CN 101170902B CN 2006800157177 A CN2006800157177 A CN 2006800157177A CN 200680015717 A CN200680015717 A CN 200680015717A CN 101170902 B CN101170902 B CN 101170902B
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
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- 150000003606 tin compounds Chemical class 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
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- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
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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
- 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
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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
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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
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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
- A01N25/26—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 in coated particulate form
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- A—HUMAN NECESSITIES
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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
- A01N25/26—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 in coated particulate form
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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
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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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/007—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process employing compositions comprising nanoparticles
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- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
Abstract
本发明涉及细碎聚合物粒子的水分散体形式的含水杀虫剂组合物,其中细碎聚合物粒子包含至少一种在25℃,1013毫巴下在水中溶解度为不大于5g/l的杀虫有机活性成分且通过动态光散射测定平均粒度为不大于300nm,其中聚合物粒子包含至少一种阳离子表面电荷的杀虫活性成分且其中包含活性成分的聚合物粒子的水分散体可通过使烯属不饱和单体M的单体组合物经受自由基水乳液聚合而得到,其中烯属不饱和单体M包含至少一种溶解形式的杀虫活性成分。本发明还涉及这种含水杀虫剂组合物在保护木质纤维素材料,尤其是木材不受有害昆虫侵袭中的用途。
Description
本发明涉及细碎聚合物粒子水分散体形式的含水杀虫剂组合物,其包含至少一种在25℃,1013毫巴下在水中溶解度为不大于5g/l的杀虫有机活性成分,涉及这种含水杀虫剂组合物在保护木质纤维素材料,尤其木材不受有害昆虫侵袭中的用途。
已知基于木质纤维素材料的材料,尤其是木材基材料处于有害昆虫如木材破坏性甲虫、蚂蚁和/或白蚁侵袭的危险中。由于侵袭可导致损害,以及在极端情况下导致材料的完全破坏,大量努力来保护这种材料对抗这种侵袭。
由于它们的固有气味和致癌物的可能性,基于焦油的传统木材防腐剂如蒽油不具吸引力。这就是为什么定义的有机活性成分现今用于此目的。由于这些活性成分通常为不溶于水的物质,通常将它们配制成在有机溶剂中的溶液(见Ullmann′s Encyclopedia of E.H.Pommer,“Wood,Preservation”第2章,在Ullmann′s Encyclopedia of Industrial Chemistry中,第5版,CD-ROM版,Wiley-VCH Weinheim 1997)。然而,溶剂的使用需要额外的费用,此外由于工作卫生和环境原因而不理想。此外,存在这样的风险:活性成分在大气影响下浸出(leach)使得这种杀虫整理的耐大气腐蚀性通常不令人满意。
US 3,400,093公开了通过烯属不饱和单体的乳液聚合而制备的含杀虫剂的聚合物水分散体,其中用于聚合的单体包含溶解的不溶于水的杀虫活性成分。其中所描述的含杀虫剂的聚合物分散体用于制备水基涂料组合物如分散性涂料,以及意欲确保涂层的杀虫整理。然而,这些聚合物分散体不适于保护木材。
较早的德国专利申请102004020332.6描述了包含至少一种在25℃,1013毫巴下在水中的溶解度不大于5g/l的杀真菌有机活性成分和由动态光散射测定平均粒度为不大于300nm的细碎聚合物的含水活性成分制剂,其中细碎聚合物的聚合物粒子包含活性成分且其中聚合物主要由在25℃下在水中的溶解度为不大于30g/l的烯属不饱和单体组成。这些活性成分组合物适用于保护木材不受木材破坏性真菌损害。
较早的德国专利申请102004037850.9描述了包含至少一种在25℃,1013毫巴下在水中的溶解度不大于5g/l的作物保护剂如杀虫、杀真菌、杀螨或除草活性成分,以及细碎聚合物的含水活性成分组合物,其中活性成分组合物可通过多步乳液聚合方法在固体活性成分粒子的含水悬浮液中得到,其中悬浮液中的活性成分粒子的平均粒度通过动态光散射测定为1200nm。这得到聚合物/活性成分粒子,其中粒子形状的活性成分以它涂覆有乳液聚合物的形式存在。
因此,本发明基于提供微溶于水,即在25℃,1013毫巴下在水中的溶解度小于5g/l,尤其小于1g/l的杀虫活性成分的含水组合物的技术问题,所述组合物有利地适用于保护木质纤维素材料,尤其是木材不受木材破坏性昆虫的侵袭。尤其是组合物应仅包含少量,或没有挥发性有机化合物如有机溶剂。此外,甚至当曝露于水中时,活性成分应不或基本上不从处理的材料中浸出。此外,含水活性成分组合物应比常规有机活性成分的悬浮液或微乳液更稳定。
令人惊讶的是,已发现该技术问题通过含水活性成分组合物而解决,其中不或仅微溶于水的杀虫活性成分存在于不溶于水的细碎聚合物的聚合物粒子中,通过动态光散射测定聚合物粒子的平均粒度为不大于500nm且具有阳离子表面电荷,以及其中包含活性成分的聚合物粒子的水分散体可通过使烯属不饱和单体M的单体组合物经受自由基水乳液聚合而得到,其中烯属不饱和单体M以溶解的形式包含至少一种杀虫活性成分。
本发明因此涉及细碎聚合物粒子的水分散体形式的杀虫剂组合物,其中细碎聚合物粒子包含至少一种在25℃,1013毫巴下在水中溶解度为不大于5g/l的杀虫有机活性成分且通过动态光散射测定平均粒度为不大于500nm,尤其是不大于300nm,其中包含至少一种杀虫活性成分的聚合物粒子具有阳离子表面电荷且其中包含活性成分的聚合物粒子的水分散体可通过使烯属不饱和单体M的单体组合物经受自由基水乳液聚合而得到,其中烯属不饱和单体M包含至少一种溶解形式的杀虫活性成分。
本发明组合物呈杀虫活性成分的稳定含水制剂的形式,其不溶于水,或仅微溶于水,其中制剂原则上适合于需要实现有效保护材料不受有害昆虫如木材破坏性甲虫、蚂蚁或白蚁侵袭的所有应用。尽管杀虫有机活性成分掺入聚合物基质中这一事实,有效保护所需的活性成分施用率不比使用常规溶剂基活性成分配制剂时更高,事实上在某些情况下更低。此外,改善活性成分在木质纤维素材料中的渗透,使得甚至当材料表面被处理或破坏时还保持保护。此外,这些组合物导致特征为对大气影响高度稳定性且较少趋于浸出的材料的杀虫整理。本发明因此还涉及这种含水组合物在防治昆虫,尤其是防治木材破坏性昆虫如白蚁、蚂蚁和木材破坏性甲虫中的用途。这里以及下文中,术语防治/防治包含防止或避免有害昆虫的侵袭以及昆虫在侵袭材料中的破坏。
本发明组合物特别适用于在木材和其他木质纤维素材料中防治有害昆虫,尤其是保护这些材料不受有害昆虫侵袭。本发明的特别实施方案因此涉及这种组合物在保护木质纤维素材料,尤其是木材不受有害昆虫侵袭,尤其是不受木材破坏性昆虫如木材破坏性甲虫、蚂蚁或白蚁侵袭,以及有害昆虫在侵袭的材料中的破坏。
然而,本发明含水组合物还适用于需要防治有害昆虫的其他应用,例如用于防治植物损害性昆虫的作物保护,种子处理以及用作土壤处理组合物。
在此所述的细碎聚合物的粒度为重均粒度,它们可通过动态光散射测定。本文中的方法为熟练工人已知的,例如由H.Wiese in D.Distler,Polymerdispersionen[聚合物水分散体],Wiley-VCH 1999,第4.2.1章,第40页及随后各页,和其中引用的文献,和H.Auweter,D.Horn,J.Colloid Interf.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。平均粒度通常为10-300nm,尤其是20-250nm,特别优选30-200nm,非常特别优选30-150nm。
在本发明组合物中,聚合物粒子具有正表面电荷,即在它们的表面上它们具有补偿任何可存在的负电荷的正电荷。众所周知,这种表面电荷可例如通过待聚合的单体M而实现,其包含阳离子单体和/或具有至少一种能在水中质子化的基团的单体(单体M-k)。众所周知,正表面电荷也可通过在表面活性物质如表面活性剂和保护胶体的存在下进行乳液聚合而实现,而表面活性物质带正电荷和/或具有至少一种能在水中质子化的官能团(参看US 5,874,524)。这种物质在下文中也称作表面活性物质O-k。当然,阳离子单体M-k或能在水中质子化的单体M-k,和/或表面活性物质O-k的用量将使得由此引入的这些物质的正电荷支配用于聚合的单体和表面活性物质中的任何负电荷或酸性基团,即能去质子化的基团。不想被理论束缚,假设不溶或微溶于水的杀虫有机活性成分以由单体M形成的聚合物基质中的细碎形式存在本发明组合物中。表面电荷可借助聚合单体M和活性成分的总量相对于阳离子单体M-k和表面活性物质O-k,减具有酸基的单体,以及减阴离子表面活性物质的总量之比而估算。单体M-k或表面活性物质的用量优选使得阳离子电荷或聚合物中的碱性基团过量,为至少0.02摩尔每kg聚合物+活性成分,尤其是0.05-1.5摩尔每kg聚合物+活性成分。
在此所述阳离子电荷过量的值相应于产生于聚合物的阳离子或碱性组分的阳离子电荷量与产生于聚合物的阴离子或酸性组分的阴离子电荷量之间的差。过量阳离子电荷等于阳离子表面电荷。聚合物的阳离子或碱性组分在这里为用于制备的阳离子或碱性单体和阳离子或碱性表面活性物质二者。因此,聚合物的阴离子组分为用于制备的阴离子或酸性单体和阴离子或酸性表面活性物质二者。
适合的单体M原则上为可通过水乳液聚合方法聚合的所有烯属不饱和单体。通常单体混合物因此主要包含不溶于水或微溶于水的,即其在水中的溶解度不大于30g/l(在25℃和1013毫巴下)的单烯属不饱和单体。这些单体在下文也称作单体M1。单体M1在这些条件下在水中的溶解度尤其为0.1-20g/l。它们通常占单体M的至少60重量%,尤其是至少70重量%,优选至少80重量%,例如60-100重量%,优选70-99.5重量%,尤其是75-99.5重量%,特别优选80-99重量%,特别是90-98重量%。
单体M1包括乙烯基芳族单体如苯乙烯、α-甲基苯乙烯、叔丁基苯乙烯和乙烯基甲苯,具有3-8个,尤其是3或4个碳原子的α,β-单烯属不饱和单羧酸和二羧酸与C1-C10链烷醇或与C5-C8环烷醇的酯,尤其是丙烯酸的酯、甲基丙烯酸的酯、巴豆酸的酯、马来酸的二酯、富马酸的二酯和衣康酸的二酯,特别优选丙烯酸与C2-C10链烷醇的酯(=丙烯酸C2-C10烷基酯)如丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正己酯、丙烯酸2-乙基己酯和丙烯酸3-丙基庚酯,和甲基丙烯酸与C1-C10链烷醇的酯如甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸正己酯等。此外,适合的单体M1为具有3-10个C原子的脂族羧酸的乙烯基和烯丙基酯如丙酸乙烯酯,和酸的乙烯酯(叔碳酸乙烯酯),乙烯基卤化物如氯乙烯和偏二氯乙烯,共轭二烯烃如丁二烯和异戊二烯,和C2-C6烯烃如乙烯、丙烯、1-丁烯和正己烯。优选的单体M1为乙烯基芳族单体,丙烯酸C2-C10烷基酯,尤其是丙烯酸C2-C8烷基酯,特别是丙烯酸叔丁酯,和甲基丙烯酸C1-C10烷基酯,尤其是甲基丙烯酸C1-C4烷基酯。尤其是,至少50重量%的单体M1选自乙烯基芳族单体,尤其是苯乙烯,甲基丙烯酸与C1-C4链烷醇的酯,尤其是甲基丙烯酸甲酯和丙烯酸叔丁酯,以及至多50重量%的单体M1选自其他单体M1,尤其是丙烯酸C2-C8烷基酯。特别优选的单体M1为乙烯基芳族单体,尤其是苯乙烯,和乙烯基芳族单体与上述丙烯酸C2-C8烷基酯和/或甲基丙烯酸C1-C4烷基酯的混合物,尤其是基于单体M1的总量,乙烯基芳族物质占至少60重量%,例如60-95重量%的那些混合物。
其他特别优选的单体M1为甲基丙烯酸C1-C4烷基酯,尤其是甲基丙烯酸甲酯,和甲基丙烯酸C1-C4烷基酯与丙烯酸C2-C4烷基酯和/或乙烯基芳族物质的混合物,尤其是甲基丙烯酸C1-C4烷基酯含量,特别是甲基丙烯酸甲酯的含量,基于单体M1的总量为至少60重量%,例如60-95重量%的混合物。
在本发明的第一个实施方案中,单体M因此包含至少一种具有至少一种阳离子基团和/或至少一种能在含水环境中质子化的基团的单烯属不饱和单体M-k。然后,单体M-k的量基于单体M的总量通常为0.1-30重量%,尤其是0.5-20重量%,特别是1-15重量%。
适合的单体M-k为具有能质子化的氨基、季铵基、能质子化的亚氨基或季铵化的亚氨基的那些。具有能质子化的亚氨基的单体的实例为N-乙烯基咪唑和乙烯基吡啶。具有季铵化的亚氨基的单体的实例为N-烷基乙烯基吡啶盐和N-烷基-N′-乙烯基咪唑啉盐如N-甲基-N′-乙烯基咪唑氯化物或metosulfate。
其中优选的单体M-k尤其为式I的单体:
其中
R1为氢或C1-C4烷基,尤其是氢或甲基,
R2、R3各自独立地为C1-C4烷基,尤其是甲基,以及
R4为氢或C1-C4烷基,尤其是氢或甲基,
Y代表氧、NH或NR5,其中R5=C1-C4烷基,
A代表任选间隔1、2或3个非相邻氧原子的C2-C8亚烷基,例如1,2-乙二基、1,2-或1,3-丙二基、1,4-丁二基或2-甲基-1,2-丙二基,以及
X-代表阴离子同等物,例如卤素如Cl-、BF4 -、HSO4 -、1/2SO4 2-或CH3OSO3 -等,
以及对于R4=H式I的单体的游离碱。
式I的单体的实例为丙烯酸2-(N,N-二甲基氨基)乙基酯、甲基丙烯酸2-(N,N-二甲基氨基)乙基酯、2-(N,N-二甲基氨基)乙基丙烯酰胺、3-(N,N-二甲基氨基)丙基丙烯酰胺、3-(N,N-二甲基氨基)丙基甲基丙烯酰胺、2-(N,N-二甲基氨基)乙基甲基丙烯酰胺、丙烯酸2-(N,N,N-三甲基铵)乙基酯氯化物、甲基丙烯酸2-(N,N,N-三甲基铵)乙基酯氯化物、2-(N,N,N-三甲基铵)乙基甲基丙烯酰胺氯化物、3-(N,N,N-三甲基铵)丙基丙烯酰胺氯化物、3-(N,N,N-三甲基铵)丙基甲基丙烯酰胺氯化物、2-(N,N,N-三甲基铵)乙基丙烯酰胺氯化物,以及对应的硫酸氢盐、metosulfate、四氟硼酸盐和硫酸盐。
除了单体M1和如果合适的话可存在的单体M-k外,单体M还包含其它烯属不饱和单体M2。单体M2包括:
-具有至少一个酸基或至少一个阴离子基团的单烯属不饱和单体M2a,尤其是具有一个磺酸基、一个膦酸基或一个或两个羧酸基的单体M2a,和单体M2a的盐,尤其是碱金属盐,例如钠盐或钾盐,和铵盐。单体M2a包括烯属不饱和磺酸,尤其是乙烯基磺酸、2-丙烯酰氨基-2-甲基丙磺酸、2-丙烯酰氧基乙磺酸和2-甲基丙烯酰氧基乙磺酸、3-丙烯酰氧基-和3-甲基丙烯酰氧基丙磺酸、乙烯基苯磺酸和它们的盐,烯属不饱和膦酸如乙烯基膦酸、乙烯基膦酸二甲基酯和它们的盐,和α,β-烯属不饱和C3-C8单羧酸和C4-C8二羧酸,尤其是丙烯酸、甲基丙烯酸、巴豆酸、马来酸、富马酸和衣康酸。单体M2a基于单体M的总量,通常占不大于10重量%,优选不大于5重量%,例如0.1-10重量%,尤其例如0.2-5重量%,单体M2a的量的选择使得单体M2a所贡献的阴离子电荷不超过表面活性物质或单体M-k贡献的阳离子电荷。在特别优选的实施方案中,单体M不包含或包含小于0.1重量%的单体M2a。
-在25℃下在水中的溶解度为至少50g/l,尤其在25℃下为至少100g/l的单烯属不饱和中性单体M2b。实例为上述烯属不饱和羧酸的酰胺,尤其是丙烯酰胺和甲基丙烯酰胺,烯属不饱和腈如甲基丙烯腈和丙烯腈,上述α,β-烯属不饱和C3-C8单羧酸和C4-C8二羧酸的羟基烷基酯,尤其是丙烯酸羟基乙基酯、甲基丙烯酸羟基乙基酯、丙烯酸2-和3-羟基丙基酯、甲基丙烯酸2-和3-羟基丙基酯,上述单烯属不饱和单羧酸和二羧酸与C2-C4聚亚烷基二醇的酯,尤其是这些羧酸与聚乙二醇或与烷基聚乙二醇的酯,分子量通常为100-3000的(烷基)聚乙二醇残留物。此外单体M2b包括脂族C1-C10羧酸的N-乙烯基酰胺和N-乙烯基内酰胺,例如N-乙烯基甲酰胺、N-乙烯基乙酰胺、N-乙烯基吡咯烷酮和N-乙烯基己内酰胺。单体M2b将优选基于单体M的总量占不大于30重量%,尤其不大于20重量%,例如0.1-20,尤其0.5-10重量%。
-具有两个或多个非共轭烯属不饱和双键的单体M2c。它们将基于单体M的总量通常占不大于5重量%,尤其不大于2重量%,例如0.01-2重量%,尤其0.05-1.5重量%。在尤其优选的实施方案中,单体M不包含或包含小于0.05重量%的单体M2c。
此外,已证明有利的是包含在本发明组合物中的聚合物的玻璃化转变温度Tg为至少10℃,优选至少20℃,尤其是至少30℃,特别是至少50℃。尤其是,玻璃化转变温度将不超过180℃,特别优选130℃。如果本发明活性成分组合物包含大量具有不同玻璃化转变温度的聚合物-以阶梯增长形式的,或芯-壳聚合物,包括具有黑莓、树莓或半月形态的多相聚合物,或以不同聚合物的混合物形式-,则玻璃化转变温度为至少10℃,优选至少20℃,尤其是至少30℃,特别是至少50℃的聚合物占至少40重量%。
在本文中玻璃化转变温度Tg应理解为根据ASTM D 3418-82通过差示扫描量热法(DSC)测定的中点温度(参看Ullmann′s Encyclopedia ofIndustrial Chemistry,第5版,第A 21卷,VCH Weinheim 1992,第169页,和Zosel,Farbe und Lack 82(1976),第125-134页,还见DIN 53765)。
在本文中,根据Fox(T.G.Fox,Bull.Am.Phys.Soc.(Ser.II)1,123[1956]和Ullmannsder technischen Chemie,Weinheim(1980),第17-18页)有助于估算共聚物P的玻璃化转变温度Tg,高分子量弱交联的共聚物的玻璃化转变温度的良好近似值由如下等式给出:
其中X1、X2、...、Xn表示单体1、2、...、n的质量分数,Tg 1、Tg 2、...、Tg n表示在每种情况下单体1、2、...、n之一仅构成的聚合物的玻璃化转变温度,以开氏(Kelvin)温度表示。上述聚合物例如从Ullmann′s Encyclopediaof Industrial Chemistry,VCH,Weinheim,第A 21卷(1992)第169页或J.Brandrup,E.H.Immergut,Polymer Handbook第3版,J.Wiley,NewYork 1989中已知。
至少一种杀虫活性成分可基本上均匀分布于本发明杀虫剂组合物的聚合物粒子中。然而,聚合物粒子还可含具有不同活性成分浓度的区域。在这种情况下,具有高活性成分浓度的区域和具有低活性成分浓度的区域可以呈芯-壳排列的形式(芯-壳形态),相互部分渗透(半月形态)或如果合适的话嵌入基质或排列在聚合物基质上(黑莓或树莓形态)的液滴形或球形区域的形式。
在本发明的优选实施方案中,聚合物粒子含具有高活性成分浓度的区域和具有低活性成分浓度的区域,其中前者排列在聚合物粒子的较外部区域中,以及后者排列在聚合物粒子的较内部区域中。例如,具有较高浓度的区域在具有较低活性成分浓度的芯周围形成不间断或间断的壳,或具有较高浓度的区域形成液滴或球体,其主要部分排列在具有较低浓度的芯区域上或嵌入这个芯区域的表面。
具有较高活性成分浓度的区域优选包含至少60重量%,尤其是至少80重量%,至多100重量%存在于组合物中的杀虫活性成分,而具有较低活性成分浓度的区域将通常包含不大于40重量%,常常不大于20重量%活性成分,或没有活性成分。具有高活性成分浓度的区域与具有低活性成分浓度的区域的重量比通常为1∶10-10∶1,尤其是4∶1-1∶4。区域间的浓度差通常为至少0.1g/100g聚合物,尤其是至少1g/100g聚合物,例如0.1-50g/100g聚合物,尤其是1-20g/100g聚合物。
在具有高和低活性成分浓度的区域中的聚合物组分各自可以相同或不同,优选至少在单体M1类型方面不同。根据本发明第一个实施方案,形成具有高活性成分浓度区域的单体M1选自甲基丙烯酸C1-C4烷基酯和至少60重量%,尤其是至少80重量%甲基丙烯酸C1-C4烷基酯与至多40重量%,尤其是至多20重量%不同于这些的单体M1的混合物,而形成具有低活性成分浓度区域的单体M1选自乙烯基芳族物质和至少60重量%,尤其是至少80重量%乙烯基芳族物质与至多40重量%,尤其是至多20重量%不同于这些的单体M1的混合物。根据本发明第二个实施方案,形成具有低活性成分浓度区域的单体M1选自甲基丙烯酸C1-C4烷基酯和至少60重量%,尤其是至少80重量%甲基丙烯酸C1-C4烷基酯与至多40重量%,尤其是至多20重量%不同于这些的单体M1的混合物,而形成具有高活性成分浓度区域的单体M1选自乙烯基芳族物质和至少60重量%,尤其是至少80重量%乙烯基芳族物质与至多40重量%,尤其是至多20重量%不同于这些的单体M1的混合物。根据本发明第三个实施方案,形成具有低活性成分浓度区域的单体M1选自甲基丙烯酸C1-C4烷基酯和至少90重量%甲基丙烯酸C1-C4烷基酯与至多10重量%不同于这些的单体M1的混合物,而形成具有高活性成分浓度区域的单体M1选自20-85重量%,尤其是50-80重量%甲基丙烯酸C1-C4烷基酯与15-80重量%,尤其是20-50重量%不同于这些的单体M1,尤其是乙烯基芳族物质的混合物。在这些实施方案中,甲基丙烯酸甲酯为优选的甲基丙烯酸C1-C4烷基酯。在这些实施方案中,苯乙烯为优选的乙烯基芳族物质。此外已证明有利的是形成高活性成分浓度区域的单体包含大多数,尤其是至少80重量%。在本文中,每种情况下所有以重量%表示的数据指形成各自区域的单体M1。此外,已证明有利的是形成高活性成分浓度区域的单体包含大多数,尤其是至少80重量%,或所有用于聚合的单体M-k。因此,基于形成高活性成分浓度区域的单体的重量,单体M-k的百分数优选0.5-40重量%,尤其是1-20重量%。此外已证明有利的是形成低活性成分浓度区域的单体包含至少一种交联单体,例如单体M2c。因此,基于形成低活性成分浓度区域的单体的重量,单体M2c的百分数优选0.01-4重量%,尤其是0.05-2重量%。
本发明组合物包含一种或多种在25℃,1013毫巴下具有低水溶性,通常不大于5g/l,优选不大于3g/l,尤其是不大于1g/l,例如0.001-1g/l或0.002-0.5g/l的杀虫活性成分。通常,它们呈有机物质的形式,尤其是具有所定义的组成,即定义的经验公式的化合物的形式,或具有所定义的组成的化合物的混合物的形式。通常,它们呈分子量不大于500道尔顿的低分子量物质的形式。通常,杀虫活性成分在至多聚合温度下以至少使用的量可溶于单体M中。通常,有利的是在25℃,1013毫巴下在单体M中的溶解度为1g/l。适合的杀虫成分的实例为作为杀虫剂在Compendium ofPesticide Common Names:http://www.hclrss.demon.co.uk/class-insecticides.html(常用名索引)中列出的化合物。这些例如包括:
·有机(硫代)磷酸酯类如高灭磷(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)、敌敌畏(dichlorphos)、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)、特丁磷(terbufos)、三唑磷(triazophos)、敌百虫(trichlorfon);
·氨基甲酸酯类如棉铃威(alanycarb)、丙硫克百威(benfuracarb)、虫威(bendiocarb)、甲萘威(carbaryl)、丁硫克百威(carbosulfan)、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)、唑蚜威(triazamate);
·合成除虫菊酯类如丙烯菊酯(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和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)、炔酮菊酯I、炔酮菊酯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)、四氟菊酯(transfluthrin)、己体氯氰菊酯(zeta-cypermethrin);
·节肢动物生长调节剂如a)几丁质合成抑制剂;例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(flufenoxuron)、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)、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)、双苯酰肼(tebufenozide);c)保幼激素类似物如蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威(fenoxycarb);d)类脂生物合成抑制剂,如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和spirotetramate;
·新烟碱类(neonicotinoids)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)、噻虫啉(thiacloprid);
·吡唑杀虫剂(GABA拮抗剂)如acetoprole、乙虫清(ethiprole)、氟虫腈(fipronil)、pyriprole、pyrafluprole、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)、氨基腙(amidrazone)、amidoflumat、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(fenazaq uin)、伐虫脒(formetanate)、伐虫脒盐酸盐(formetanatehydrochloride)、灭蚁腙(hydramethylnon)、二唑虫(indoxacarb)、metaflumizon(=4-{(2Z)-2-({[4-(三氟甲氧基)苯胺基]羰基}亚肼基)-2-[3-(三氟甲基)苯基]乙基}苄腈)、哒螨酮(pyridaben)、拒嗪酮(pymetrozine)、艾克敌105(spinosad)、吡螨胺(tebufenpyrad)、flupyrazaphos、氟啶虫酰胺(flonicamid)、啼虫胺(flufenerim)、氟虫酰胺(flubendiamide)、双三氟虫脲(bistrifluron)、NC512、benclothiaz、cyflumethofen、milbermectin、cyclometofen、lepimectin、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin)、N-乙基-2,2-二卤代-1-甲基环丙烷甲酰胺-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-4-三氟甲苯基)腙、硫环杀(thiocyclam)、啶虫丙醚(pyridalyl)和WO 98/05638所描述的下式化合物:
这些中优选有效对抗木材破坏性昆虫,尤其是对抗木材破坏性甲虫、白蚁(等翅目(Isoptera))和蚁科(Formicidae),特别是对抗如下木材破坏性昆虫的杀虫剂:
鞘翅目(Coleoptera)(甲虫):
·天牛科(Cerambycidae),例如北美家天牛(Hylotrupes bajulus)、紫色扁天牛(Callidium violaceum);
·粉蠹科(Lyctidae),例如栎粉蠹(Lyctus linearis)、褐粉蠢(Lyctusbrunneus);
·长蠹科(Bostrichidae),例如竹蠹(Dinoderus minutus);
·窃蠹科(Anobiidae),例如家具窃蠹(Anobium punctatum)、红毛窃蠢(Xestobium rufovillosum);
·筒蠹科(Lymexylidae),例如Lymexylon navale;
·长小蠹科(Platypodidae),例如Platypus cylindrus;
·拟天牛科(Oedemeridae),例如Nacerda melanura。
膜翅目(Hymenoptera)(膜翅目昆虫(hymenopterons)):
·蚁科(Formicidae),例如Camponotus abdominalis、黄墩蚁(Lasiusflavus)、Lasius brunneus、黑草蚁(Lasius fuliginosus);
等翅目(Isoptera)(白蚁):
·Calotermitidae,例如Calotermes flavicollis、Cryptothermes brevis;
·草白蚁科(Hodotermitidae),例如北美湿木白蚁(Zootermopsisangusticollis)、内华达动白蚁(Zootermopsis nevadensis);
·鼻白蚁科(Rhinotermitidae),例如黄肢散白蚁(Reticulitermesflavipes)、欧洲散白蚁(Reticulitermes lucifugus)、台湾乳白蚁(Coptotermesformosanus)、矛颚家白蚁(Coptotermes acinaciformis);
·Mastotermitidae wie Mastotermes darwiniensis。
它们尤其包括来自合成除虫菊酯类、氨基甲酸酯类、有机(硫代)磷酸酯类、节肢动物生长调节剂如几丁质合成抑制剂、蜕皮激素拮抗剂、保幼激素类似物、类脂生物合成抑制剂、新烟碱类、吡唑杀虫剂和氟唑虫清类的杀虫活性成分。
尤其优选在Biocidal Products Directive of the European Union(COMMISSION REGULATION(EC)No.2032/2003of November 4,2003)在分类08(木材防腐剂)和18(杀虫剂、杀螨剂和防治其他节肢动物的物质)中提到的那些杀虫活性成分。
杀虫活性成分基于形成聚合物的单体M,通常以0.1-50重量%,优选0.2-30重量%,尤其是0.5-20重量%的量存在于本发明活性成分组合物中。
原则上,包含在本发明组合物中的聚合物粒子除至少一种杀虫活性成分外还可包含其他活性成分。尤其是聚合物粒子包含杀虫活性成分作为唯一活性成分。在本发明的一个实施方案中,杀真菌剂活性成分的量基于包含在聚合物粒子中的杀虫活性成分为<1重量%,或基于聚合物和活性成分的总量为<0.1重量%。
本发明组合物的聚合物中的活性成分的总量基于聚合物,或基于形成聚合物的单体M优选占0.2-50重量%,尤其是0.5-30重量%,尤其优选1-20重量%。
为将聚合物粒子稳定在含水介质中,本发明含水组合物通常包含表面活性物质。这些不仅包括保护胶体,还包括低分子量乳化剂,与保护胶体相反,后者的分子量通常小于2000g/mol,尤其是小于1000g/mol(质量平均)。保护胶体和乳化剂可以为阳离子、阴离子、中性或两性离子类型之一。
阳离子表面活性物质可以呈阳离子乳化剂的形式,也可呈阳离子保护胶体的形式,其与乳化剂的区别通常主要在于更高的分子量,通常为至少1000道尔顿,尤其是1000-50000道尔顿(数均)。
阳离子乳化剂通常呈如下化合物的形式:具有至少一种通常6-30个C原子,尤其是8-22个C原子的长链烃基和至少一种质子化或尤其是季铵化的氮原子如以铵、吡啶或咪唑基团形式。除此之外,阳离子乳化剂也可具有低聚醚基团,尤其是低聚氧化乙烯基团(乙氧基化度通常为2-40)。
阳离子乳化剂的实例包含季铵盐,例如三甲基C6-C30烷基铵盐和三乙基C6-C30烷基铵盐如椰油三甲基铵盐、三甲基鲸蜡基铵盐,二甲基二C4-C20烷基铵盐和二乙基二C4-C20烷基铵盐如二癸基二甲基铵盐和二椰油二甲基铵盐,甲基三C4-C20烷基铵盐和乙基三C4-C20烷基铵盐如甲基三辛基铵盐,C1-C20烷基-二-C1-C4烷基苄基铵盐如三乙基苄基铵盐和椰油苄基二甲基铵盐,乙氧基化和季铵化的C6-C30烷基胺(乙氧基化度通常为2-49)如乙氧基化度为2-20,尤其是4-8的乙氧基化油基胺的季铵化产物,甲基-二C4-C20烷基聚(氧基乙基)铵盐和乙基-二C4-C20烷基聚(氧基乙基)铵盐如二癸基甲基聚(氧基乙基)铵盐,N-C6-C20烷基吡啶盐如N-月桂基吡啶盐,N-甲基-N-C6-C20烷基吗啉盐和N-乙基-N-C6-C20烷基吗啉盐,和N-甲基-N′-C6-C20烷基咪唑啉盐和N-乙基-N′-C6-C20烷基咪唑啉盐,尤其是卤化物、硼酸盐、碳酸盐、甲酸盐、乙酸盐、丙酸盐、碳酸氢盐、硫酸盐和甲基硫酸盐。
阳离子保护胶体通常呈烯属不饱和单体的均聚物和共聚物形式,其包含基于构成阳离子保护胶体的单体总重量,以至少20重量%,尤其是至少30重量%的量掺入聚合物中的至少上述单体M-k之一。另外,保护胶体可包含掺入聚合物中的中性共聚单体。在适合作为保护胶体的共聚物中,中性共聚单体的量基于构成阳离子保护胶体的单体总量,通常占5-80重量%,尤其是10-70重量%。适合的共聚单体尤其为可与水溶混的中性单烯属不饱和单体。这些包括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-C10羧酸的N-乙烯基酰胺如N-乙烯基甲酰胺、N-乙烯基乙酰胺、N-乙烯基丙酰胺、N-乙烯基-M-甲基乙酰胺等,通常具有3-5个C原子的单烯属不饱和单羧酸的酰胺如丙烯酰胺、甲基丙烯酰胺,通常具有3-5个C原子的单烯属不饱和单羧酸的羟基烷基酯,例如丙烯酸的酯或甲基丙烯酸的酯如丙烯酸羟基乙基酯、甲基丙烯酸羟基乙基酯、丙烯酸羟基丙基酯、甲基丙烯酸羟基丙基酯、丙烯酸羟基丁基酯和甲基丙烯酸羟基丁基酯,此外还有通常具有3-5个C原子的单烯属不饱和单羧酸的酯如丙烯酸或甲基丙烯酸与低聚氧化乙烯或单烷基低聚氧化乙烯的酯。除水溶混性中性单体外,适合的共聚单体还有与水不溶混的单烯属不饱和共聚单体。这些尤其包括乙烯基芳族单体如苯乙烯、α-甲基苯乙烯、叔丁基苯乙烯和乙烯基甲苯,具有3-8个,尤其是3或4个C原子的α,β-单烯属不饱和单羧酸和二羧酸与C1-C10链烷醇或与C5-C8环烷醇的酯,尤其是丙烯酸、甲基丙烯酸、巴豆酸的酯,马来酸、富马酸和衣康酸的二酯,尤其优选丙烯酸与C2-C10链烷醇的酯(=丙烯酸C2-C10烷基酯),如丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正己酯、丙烯酸2-乙基己酯和丙烯酸3-丙基庚酯,和甲基丙烯酸与C2-C10链烷醇的酯如甲基丙烯酸乙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸正己酯等;具有3-10个C原子的脂族羧酸的乙烯基和烯丙基酯如丙酸乙烯酯,酸的乙烯基酯(叔碳酸乙烯酯),共轭二烯烃如丁二烯和异戊二烯,以及C2-C12烯烃如乙烯、丙烯、1-丁烯、正己烯和二异丁烯。
优选的保护胶体为:
-N-乙烯基-N-甲基咪唑啉盐、N-烷基乙烯基吡啶盐或式I的单体与上述水溶混性共聚单体的共聚物,其中水溶混性共聚单体的量基于构成阳离子保护胶体的单体总量占5-80重量%,尤其是10-70重量%,和
-由30-95重量%,尤其是50-90重量%至少一种选自N-乙烯基-N-甲基咪唑啉盐、N-烷基乙烯基吡啶盐和式I的单体的单体M-k,和至少一种与水不溶混的共聚单体构成的共聚物,其中这种共聚单体的量基于构成阳离子保护胶体的单体总量占5-70重量%,尤其是10-50重量%,
-由20-90重量%,尤其是30-90重量%至少一种选自N-乙烯基-N-甲基咪唑啉盐、N-烷基乙烯基吡啶盐和式I的单体的单体M-k,5-60重量%,尤其是5-40重量%至少一种与水不溶混的共聚单体与5-75重量%,尤其是5-65重量%至少一种水溶混性共聚单体构成的三元共聚物。
这种保护胶体是已知的,且例如在商品名Luviquat和Sokalan(BASFAktiengesellschaft)下市售。
此外适合的阳离子保护胶体为聚乙烯亚胺和它们的季铵化产物,以及可通过水解N-乙烯基甲酰胺的均聚物和共聚物而得到的聚乙烯胺,和它们的季铵化产物。这些保护胶体同样已知,且例如在商品名Lupasol、Hydragen和Sokalan(BASF Aktiengesellschaft)下市售。
阴离子表面活性物质的实例为阴离子乳化剂如烷基苯基磺酸盐、苯基磺酸盐、烷基硫酸盐、烷基磺酸盐、烷基醚硫酸盐、烷基酚醚硫酸盐、烷基聚乙二醇醚磷酸盐、烷基二苯基醚磺酸盐、聚芳基苯基醚磷酸盐、烷基磺基丁二酸盐、烯烃磺酸盐、石蜡磺酸盐、石油磺酸盐、牛磺酸盐、肌氨酸盐、脂肪酸、烷基萘磺酸、萘磺酸,包括它们的碱金属盐、碱土金属盐、铵盐和胺盐。
阴离子保护胶体的实例为木素磺酸,磺化萘与甲醛或与甲醛和苯酚和如果合适的话脲的缩合物,以及苯基磺酸、甲醛和脲的缩合物,木素亚硫酸盐废液,和木素磺酸盐,以及聚羧酸酯如聚丙烯酸酯、马来酸酐/烯烃共聚物(例如CP9,BASF),和上述保护胶体的碱金属盐、碱土金属盐、铵盐和胺盐。
非离子乳化剂的实例为烷基酚烷氧基化物、醇烷氧基化物、脂肪胺氧基化物、聚氧乙烯甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酸酰胺烷氧基化物、脂肪酸聚二乙醇酰胺、羊毛脂乙氧基化物、脂肪酸聚乙二醇酯、异十三醇、脂肪酸酰胺、甲基纤维素、脂肪酸酯、硅油、烷基多糖苷和甘油脂肪酸酯。
非离子保护胶体的实例为聚乙二醇、聚丙二醇、聚乙二醇/聚丙二醇嵌段共聚物、聚乙二醇烷基醚、聚丙二醇烷基醚、聚乙二醇/聚丙二醇醚嵌段共聚物,和它们的混合物。
在本发明的优选实施方案中,本发明组合物包含至少一种阳离子表面活性物质,尤其是阳离子乳化剂。
在本发明的另外优选实施方案中,本发明组合物包含至少一种阳离子表面活性物质,尤其是阳离子乳化剂,和至少一种非离子表面活性物质。
表面活性物质的总量基于单体M通常为0.2-30重量%,尤其是0.3-20重量%,尤其优选0.5-10重量%。如果需要的话,阳离子表面活性物质O-k基于待聚合单体M的总量通常以0.2-12重量%,尤其是0.5-8重量%的量使用。在阳离子乳化剂的情况下,这些通常为0.5-12重量%,阳离子保护胶体为0.1-6重量%,每种情况下基于单体M的总量。如果需要的话,非离子表面活性物质的量基于构成聚合物的单体M的总量优选0.2-12重量%,尤其是0.5-10重量%。
本发明含水组合物的制备包括烯属不饱和单体M的单体组合物的自由基水乳液聚合,其中烯属不饱和单体M包含至少一种溶解形式的杀虫活性成分。在自由基水乳液聚合期间,单体以单体M的水包油乳液的形式聚合,其中乳液的单体滴包含至少一种杀虫活性成分。这里,聚合类似于常规乳液聚合而进行,区别在于待聚合的单体乳液包含溶解于单体滴中的杀虫活性成分。
活性成分/单体溶液的水包油乳液可通过将活性成分在待聚合的单体M中的溶液加入聚合条件下的聚合容器中而原位产生。然而,优选活性成分将溶于单体M,以及产生的单体溶液将在产生的单体/活性成分乳液经受聚合反应之前转变成含水单体乳液。
适合的表面活性物质为常用于乳液聚合和已在上面作为本发明活性成分配制剂的组分而提到的乳化剂和保护胶体。常用于乳液聚合的表面活性物质的量通常在上述范围内,使得总量或部分包含在本发明组合物中的表面活性物质借助乳液聚合而提供。然而,也可在乳液聚合中仅使用部分,例如10-90重量%,尤其是20-80重量%包含在本发明组合物中的表面活性物质,以及在乳液聚合之后,在如果合适的话必须进行的任何除臭(后皂化)之前或之后,向乳液聚合中加入其余表面活性物质。
为确保阳离子表面电荷,已证明有用的是在阳离子表面活性物质的存在下进行单体M的乳液聚合。因此,在本发明的优选实施方案中,本发明活性成分组合物通过使单体组合物在阳离子表面活性物质的存在下,尤其是在阳离子乳化剂的存在下经受自由基水乳液聚合而制备。阳离子表面活性物质尤其当单体M不包含单体M-k时用于乳液聚合。然而,已证明有用的是甚至当单体M包含单体M-k时在阳离子表面活性物质O-k的存在下进行乳液聚合。
如果需要的话,阳离子表面活性物质O-k基于待聚合的单体M的总量通常以0.2-12重量%,尤其是0.5-8重量%的量使用。在阳离子乳化剂的情况下,量通常为0.5-12重量%,在阳离子保护胶体的情况下为0.1-6重量%,每种情况下基于单体M的总量。
如果适合的话,可有利的是在至少一种非离子表面活性物质,尤其是与阳离子活性物质组合存在下进行乳液聚合。适合的非离子表面活性物质为上文提到的非离子表面活性化合物。
用于乳液聚合的非离子表面活性物质的量基于待聚合的单体M的总量,通常为0.1-20重量%,尤其是0.2-17重量%。
用于乳液聚合的表面活性物质的总量基于待聚合的单体M的总量,通常为0.2-30重量%,尤其是0.5-20重量%。
通常,聚合反应通过称作单体进料方法的方法而进行,即将大批,优选至少70%,尤其是至少90%的活性成分在单体M中的溶液,或大批,优选至少70%,尤其是至少90%单体/活性成分乳液在聚合反应期间送入聚合容器。优选,单体/活性成分溶液或乳液经至少0.5小时,优选至少1小时,例如1-10小时,尤其是2-5小时加入。单体/活性成分溶液或乳液可以以恒定或变化的加入速率,例如以具有恒定加入速率或具有变化的加入速率间隔或以变化的加入速率连续加入。在加入期间,单体/活性成分溶液或乳液的组成可保持恒定或改变,可进行关于单体组成和关于活性成分性质或活性成分浓度的改变。
在本发明优选的实施方案中,单体组合物在单体加入过程中为变化的,使得在聚合物粒子中得到具有不同玻璃化转变温度的聚合物区域。这通过被称为阶梯增长聚合而实现。为此,其单体组成与玻璃化转变温度TG 1相应的第一种单体/活性成分溶液或乳液首先在第一个步骤中聚合,至此随后加入其单体组成与玻璃化转变温度TG 2相应的第二种单体/活性成分溶液或乳液(步骤2),其后如果合适的话连续加入其单体组成在每种情况下与玻璃化转变温度TG n相应的一种或多种其它单体/活性成分溶液或乳液,其中n代表所述步骤。优选逐次聚合中得到的聚合物中的各个玻璃化转变温度相差至少10K,尤其是相差至少20K,尤其优选相差至少30K,例如30K-200K,尤其是40K-160K。通常在单体量中聚合的单体的量在2步聚合的情况下将达到至少5重量%,优选至少10重量%,例如5-95重量%,尤其是10-90重量%,在三步聚合或多步聚合的情况下达到5-90重量%,或5-85重量%,尤其是10-80重量%。
其中聚合物粒子具有高活性成分浓度的区域和低活性成分浓度的区域的本发明含水活性成分组合物的制备可与已知的通过多步乳液聚合方法而制备多相乳液聚合物类似地进行,区别在于形成高活性成分区域的单体(单体Ma)具有比形成更低活性成分浓度区域的单体(单体Mb)更高的活性成分浓度。通常,单体Ma包含至少70重量%,优选至少80重量%或全部量的以溶解形式存在于组合物中的杀虫活性成分。因此,单体Mb包含其余杀虫活性成分,即不多于30重量%,尤其是不多于20重量%,或没有杀虫活性成分。
多相乳液聚合物和它们的制备方法原则上由现有技术,例如由“Emulsions Polymerization and Emulsion Polymers”(M.S.El-Asser等,编辑),Wiley,Chichester 1997,第9章,第293-326页和其中引用的参考文献;Y.C.Chen等,J.Appl.Polym.Sci.41(1991),第1049页;I.Cho等,J.Appl.Polym.Sci.30(1985),第1903;D.R.Stuterman等,Ind,Eng.Prod.Res.Dev.23(1985),第404页;S.Lee等,Polym.Chem 30(1992),第2211页;Y.C.Chen等,Macromolecules 24(1991)3779,C.L.Winzor等,Polymer 18(1992)第3797页已知。通常,它们通过至少一种形成第一单体相的第一种单体乳液和至少一种形成至少一种其他聚合物相的第二种单体乳液的序列乳液聚合而制备,可借助单体乳液的聚合顺序,也借助单体组成和聚合条件而控制聚合物粒子的形态,因此也可控制聚合物粒子中聚合相的相对排列。
由于相分离成外相和内相常常以本身已知的方式取决于相关单体组成而并不取决于聚合顺序,因此单体Ma和Mb的聚合顺序为次要的。然而,常常进行这样的程序,其中单体Mb首先聚合,单体Ma其后聚合,以便得到具有高活性成分浓度的外部区域和低活性成分浓度的内部区域的聚合物粒子。
通常,单体Ma与单体Mb的聚合通过称作单体进料方法的方法进行,即将大多数,优选至少70%,尤其是90%的活性成分在单体Ma中的溶液,或大多数,优选至少70%,尤其是90%的单体/活性成分乳液在聚合反应期间供入聚合容器中。单体/活性成分溶液或乳液的加入优选经至少0.5小时,优选至少1小时,例如1-10小时,尤其是2-5小时实现。单体/活性成分溶液或乳液的加入可以以恒定的或变化的进料速率,例如以具有恒定进料速率或具有变化进料速率间隔或具有变化的进料速率连续进行。单体/活性成分溶液或乳液的组成可在加入期间保持恒定或可改变,可进行关于单体组成和关于活性成分性质或活性成分浓度的改变。
已证明对于制备本发明活性成分组合物和活性成分组合物的特性有利的是在种子聚合物(种子胶乳)的存在下进行乳液聚合。这些呈细碎聚合物胶乳的形式,其平均粒度通常不大于100nm,尤其是不大于80nm,尤其优选不大于50nm。构成种子胶乳的单体优选选择至少90重量%,尤其是至少95重量%,常常多于99重量%单体M1,对于种子胶乳而言也可包含少量,例如0.1-10重量%,尤其是0.1-5重量%,特别是0.1-1重量%不同的单体M2,用于稳定目的,例如单体M2a。种子胶乳的玻璃化转变温度常常为至少10℃,尤其是至少50℃,常常为至少80℃。种子胶乳的量基于待聚合的单体M1的量通常为0.01-5重量%,尤其是0.1-4重量%。优选所有批料,尤其是全部种子胶乳在聚合反应开始时存在于反应容器中。种子胶乳也可在聚合容器中通过形成种子胶乳的单体的自由基乳液聚合而原位产生,形成种子胶乳的单体选自上述单体M1和M2,尤其是至少90重量%单体M1。种子胶乳的所需粒度可以以本身已知的方式借助单体/乳化剂比而控制。
适于本发明乳液聚合物的启动剂为常规适用于乳液聚合和引发单体M自由基聚合的聚合引发剂。这些包括偶氮化合物如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)二氢氯化物,和2,2’-偶氮二(2-脒基丙烷)二氢氯化物,有机或无机过氧化物如过氧化二乙酰、二叔丁基过氧化物、二戊基过氧化物、过氧化二辛酰、过氧化二癸酰、过氧化月桂酰、过氧化二苯甲酰、双(邻甲苯基)过氧化物、过氧化琥珀酰、过乙酸叔丁酯、过马来酸叔丁酯、过异丁酸叔丁酯、过新戊酸叔丁酯、过辛酸叔丁酯、过新癸酸叔丁酯、过苯甲酸叔丁酯、叔丁基过氧化物、叔丁基氢过氧化物、异丙基苯氢过氧化物、过氧-2-乙基己酸叔丁酯和过氧化二氨基甲酸二异丙酯;过硫酸的盐和氧化还原引发剂体系。
优选使用水溶性引发剂,例如阳离子偶氮化合物如偶氮二(二甲基脒基丙烷),过硫酸的盐,尤其是钠盐、钾盐或铵盐,或包含过硫酸的盐,过氧化氢或有机过氧化物如叔丁基氢过氧化物作为氧化剂的氧化还原引发剂体系。它们优选包含选自尤其亚硫酸氢钠、羟基甲烷亚磺酸钠和亚硫酸氢盐与丙酮加合物的硫化合物作为还原剂。另外适合的还原剂为含磷的化合物如亚磷酸、次磷酸盐和亚膦酸盐,以及肼或水合肼,和抗坏血酸。此外,氧化还原引发剂体系可包括加入少量氧化还原金属盐如铁盐、钒盐、铜盐、铬盐或锰盐,例如氧化还原引发剂体系抗坏血酸/硫酸铁(II)/过硫酸钠。
通常,引发剂以基于单体M的量,0.02-2重量%,尤其是0.05-1.5重量%的量使用。引发剂的最佳量将自然取决于所用的引发剂体系并且可由熟练工人在常规试验中确定。反应容器可首先装一些或所有引发剂。优选将大部分引发剂,尤其是至少80%,例如80-99.5%引发剂在聚合反应期间加入聚合反应器中。
压力和温度对于制备本发明活性成分组合物而言为次要的。温度将自然取决于所用的引发剂体系,最佳聚合温度可由熟练工人通过常规试验而确定。聚合温度通常为20-110℃,常常为50-95℃。聚合反应通常在大气压力或环境压力下进行。然而,它也可在升高的压力,例如在达3巴下或在稍微降低的压力如>800毫巴下进行。
自然地,聚合物的分子量可通过加入少量,例如基于待聚合单体M,0.01-2重量%的调节剂而调整。适合的调节剂尤其为有机硫醇化合物,其他烯丙基醇和醛。
实际聚合反应后,如果合适的话需要使本发明聚合物水分散体很大程度上没有气味物质如残余单体和其他有机挥发性组分。这可以以本身已知的方式通过物理方法通过借助蒸馏(尤其是借助蒸汽蒸馏)除去或用惰性气体汽提而实现。此外,残余单体的减少可通过自由基后聚合,尤其是使用如DE-A 4435423、DE-A 4419518和DE-A 4435422中所列的氧化还原引发剂体系而化学地进行。后聚合优选用由至少一种有机过氧化物和有机亚硫酸盐组成的氧化还原引发剂体系进行。
聚合已结束后,得到的聚合物分散体可在它们根据本发明使用之前通过加入酸或碱而达到所需的pH。
这得到分散体的聚合物粒子中包含至少一种杀虫活性成分的稳定的水分散体。另外,产生的分散体包含上述表面活性物质。产生的活性成分制剂以高稳定性和挥发性有机物的低含量为特征,挥发性有机物通常基于组合物的总重量,占不大于1重量%,常常不大于0.1重量%,尤其是不大于500ppm。这里和下文中,挥发性组分为在大气压力下沸点为200℃以下的所有有机化合物。
在第一个近似中,本发明组合物的固体含量通过活性成分和聚合物测定;它通常为10-60重量%,尤其是20-50重量%。
可因此得到的活性成分组合物可直接使用或稀释后直接使用。此外,本发明组合物可额外还包含添加剂如粘度改性添加剂(增稠剂)、消泡剂、杀菌剂和防冻剂。
适合的增稠剂为赋予配制剂假塑性流动行为,即在静止时粘度高且在搅拌状态下粘度低的化合物。就这点而言可提到的例如为多糖如Xanthan(来自Kelco的 23(Rhone-Poulenc)或(R.T.Vanderbilt),以及层状矿物,如果合适的话有机改性的层状矿物,如(Engelhardt),优选使用多糖如Xanthan
适合的防冻剂为有机多元醇,例如乙二醇、丙二醇或甘油。这些通常以基于活性物质组合物的总重量,不大于10重量%的量使用。
如果合适的话,本发明活性物质组合物可包含基于制备的配制剂的总量,1-5重量%缓冲剂以调节pH,所用缓冲剂的量和类型取决于一种活性物质或多种活性物质的化学性能。用于调节pH的缓冲剂的实例为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。
另外,本发明含水组合物可与常规基料,例如聚合物水分散体或水溶性树脂如水溶性醇酸树脂或与蜡配制。
就用于木质纤维素材料的保护,尤其是木材保存而言,本发明含水活性物质组合物也可与常规水溶性木材防腐剂,尤其是与它们的水溶液或悬浮液配制以便改善对抗木材破坏性生物体的整体有效性。就这点而言,这些例如为如下常规木材保护盐的含水制剂,例如基于硼酸的盐和碱金属硼酸盐,基于季铵化合物的盐如三甲基-和三乙基(C6-C30烷基)铵盐,例如椰油三甲基氯化铵或三甲基鲸蜡基铵盐,二甲基-和二乙基二(C4-C20烷基)铵盐,例如二癸基二甲基氯化铵、二癸基二甲基溴化铵或二椰油二甲基氯化铵,(C1-C20烷基)二(C1-C4烷基)苄基铵盐,例如椰油苄基二甲基氯化铵,或甲基-和乙基二(C4-C20烷基)聚(氧基乙基)铵盐,例如二癸基甲基聚(氧基乙基)氯化铵和丙酸盐,以及硼酸盐、碳酸盐、甲酸盐、乙酸盐、碳酸氢盐、硫酸盐和甲基硫酸盐,或铜-胺络合物的含水制剂,尤其是包含铜乙醇胺如Cu-HDO的盐的含水制剂。显然,本发明含水活性物质制剂也可与其他含水杀真菌和杀虫活性物质组合物,例如与常规杀真菌剂和杀虫剂的乳液浓缩物、悬浮液浓缩物或悬浮乳剂浓缩物配制。
可与本发明活性成分组合物一起共配制的杀真菌活性成分的实例包含Compendium of Pesticide Common Names:http://www.hclrss.demon.co.uk/class-fungicides.html(Index of commonnames)中作为杀真菌剂列出的化合物。这些例如包括:
·酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)或霜灵(oxadixyl);
·吗啉化合物,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)或链霉素(streptomycin);
·唑类,例如戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、苄氯三唑醇(diclobutrazol)、醚唑(difenoconazole)、烯唑醇(dinitroconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、酮康唑(ketoconazole)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizole)或戊叉唑菌(triticonazole);
·二羧酰亚胺类,如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)或烯菌酮(vinclozolin);
·二硫代氨基甲酸盐类,福美铁(ferbam)、代森钠(nabam)、代森锰(maneb)、代森锰锌(mancozeb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美双(thiram)、福美锌(ziram)或代森锌(zineb);
·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)、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)、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)或嗪氨灵(triforine);
·硝基苯基衍生物,如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)或异丙消(nitrothal-isopropyl);
·苯基吡咯类,如拌种咯(fenpiclonil)或氟菌(fludioxonil);
·嗜球果伞素类(strobilurins),如醚菌胺(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);
·其他杀真菌剂,例如噻二唑素(acibenzolar-S-methyl)、苯甲酰苯甲酸酯(benzoyl benzoate)、十二烷基胍氢氯化物(dodecylguanidinehydrochloride)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、哒菌清(diclomezine)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、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)或苯酰菌胺(zoxamide);
·次磺酸衍生物,尤其是亚磺酰胺如敌菌丹(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);
此外,它们包括:
·碘化合物,例如二碘甲基对甲苯基砜、3-碘-2-丙炔醇、4-氯苯基-3-碘炔丙基缩甲醛、3-溴-2,3-二碘-2-丙烯基乙基碳酸酯、2,3,3-三碘烯丙基醇、3-溴-2,3-二碘-2-丙烯基醇、3-碘-2-丙炔基-正丁基氨基甲酸酯、3-碘-2-丙炔基-正己基氨基甲酸酯、3-碘-2-丙炔基苯基氨基甲酸酯、O-1-(6-碘-3-氧代己-5-炔基)丁基氨基甲酸酯、O-1-(6-碘-3-氧代己-5-炔基)苯基氨基甲酸酯、napcocide;
·苯酚衍生物,例如三溴苯酚、四氯苯酚、3-甲基-4-氯苯酚、二氯芬、邻苯基苯酚、间苯基苯酚、2-苄基-4-氯苯酚;
·异噻唑啉酮,例如N-甲基异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、4,5-二氯-N-辛基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮;
·(苯基)异噻唑啉酮,例如1,2-苯基异噻唑-3(2H)-酮、4,5-三甲基异噻唑-3-酮、2-辛基-2H-异噻唑-3-酮;
·吡啶,例如1-羟基-2-吡啶硫酮(及其Na、Fe、Mn、Zn盐)、四氯-4-甲基磺基吡啶;
·金属皂,例如环烷酸锡、环烷酸铜、环烷酸锌、辛酸锡、辛酸铜、辛酸锌、2-乙基己酸锡、2-乙基己酸铜、2-乙基己酸锌、油酸锡、油酸铜、油酸锌、磷酸锡、磷酸铜、磷酸锌、苯甲酸锡、苯甲酸铜或苯甲酸锌;
·有机锡化合物,例如三丁基(TBT)锡化合物如三丁基锡和三丁基(单环烷酰氧基)锡衍生物;
·二硫代氨基甲酸二烷基酯和二硫代氨基甲酸二烷基酯的Na和Zn盐、二硫化四甲基秋兰姆;
·腈,例如2,4,5,6-四氯间苯二甲腈;
·苯基噻唑,例如2-巯基苯并噻唑;
·喹啉,例如8-羟基喹啉和它们的Cu盐;
3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-氧杂噻嗪4-氧化物(bethoxazin)。
就本发明组合物用于保护木质纤维素材料的用途而言,优选的杀真菌剂尤其是例如有效对抗霉菌、木材脱色和木材破坏性真菌或其他木材破坏性微生物的那些:木材破坏性微生物的实例为:
木材脱色真菌:
·子囊菌纲(Ascomycetes),如线嘴壳属(Ophiostoma sp.)(如Ophiostomapiceae、Ophiostoma piliferum)、长喙壳菌属(Ceratocystis sp.)(如Ceratocystis coerulescens)、出芽短梗霉(Aureobasidium pullulans)、Sclerophoma sp.(如Sclerophoma pityophila);
·半知菌纲(Deuteromycetes),例如曲霉属(Aspergillus sp.)(如黑曲霉(Aspergillus niger))、枝孢属(Cladosporium sp.)(如球孢枝孢菌(Cladosporium sphaerospermum))、青霉菌属(Penicillium sp.)(如绳状青霉(Penicillium funiculosum))、木霉属(Trichoderma sp.)(如绿色木霉(Trichoderma viride))、链格孢属(Alternaria sp.)(如交链孢菌(Alternariaalternate))、拟青霉菌属(Paecilomyces sp.)(如宛氏拟青霉(Paecilomycesvariotii));
·接合菌纲(zygomycetes),例如毛霉(Mucor sp.)属(如冻土毛霉(Mucorhiemalis));
木材破坏性真菌:
·子囊菌纲(Ascomycetes),例如毛壳菌属(Chaetomium sp.)(如球毛壳菌(Chaetomium globosum))、腐质霉属(Humicola sp.)(如灰色腐殖霉(Humicola grisea))、彼得壳属(Petriella sp.)(如Petriella setifera)、毛束霉属(Trichurus sp.)(如螺旋毛束霉(Trichurus spiralis));
·担子菌纲(Basidiomycetes),例如粉孢革菌属(Coniophora sp.)(如粉孢革菌(Coniophora puteana))、革盖菌属(Coriolus sp.)(如彩绒革盖菌(Coriolus versicolor))、粘褶菌属(Gloeophyllum sp.)(如密粘褶菌(Gloeophyllum trabeum))、香菇属(Lentinus sp.)(如洁丽香菇(Lentinuslepideus))、侧耳属(Pleurotus sp.)(如糙皮侧耳(Pleurotus ostreatus))、卧孔菌属(Poria sp.)(如绵腐卧孔菌(Poria placenta)、纤维卧孔菌(Poriavaillantii))、干朽菌属(Serpula sp.)(如干朽菌(Serpula lacrymans))和干酪菌属(Tyromyces sp.)(如瘤盖干酷菌(Tyromyces palustris))。
来自康唑组、吗啉组、嗜球果伞素类组、噻唑组、亚磺酰胺组和碘化合物组的杀真菌活性成分特别适于对抗这些。尤其优选Biocidal ProductsDirective of the European Union(COMMISSION REGULATION(EC)No.2032/2003 of 4th November,2003),分类08(木材防腐剂)中提到的那些杀真菌剂。
本发明含水活性成分组合物可以以基于组合物的总重量,0.1-30重量%,优选0.2-25重量%,尤其是0.5-20重量%的量包含杀真菌活性成分。
通过将本发明含水活性成分组合物与上述活性物质的常规含水制剂混合,如果常规制剂包含不同于本发明含水活性成分组合物的活性成分,则首先得到活性谱的扩展。其次,本发明活性成分组合物的优点,尤其是改善的对于木质纤维素材料,尤其是对于木材的附着力不会通过与常规含水活性成分制剂配制而损失。因此,常规含水活性成分制剂的应用性能可通过与相同活性成分的本发明含水活性成分组合物配制而改善。
本发明活性成分组合物具有大量优点。首先,这些为不溶于水或仅微溶于水的杀虫活性成分的稳定含水配制剂。尤其是,甚至当使用例如用于用杀虫活性成分浸渍木材的方法中发生的急剧条件时,活性成分的常规悬浮液配制剂中和微分散体或纳米分散体中观察到的相分离问题未观察到,活性成分的沉降未观察到。用常规添加比用可比的常规配制剂的挥发性有机化合物含量更低,并且与活性成分的微分散体或纳米分散体相比,同时基于所用的活性成分,乳化剂比例更低。活性成分在水的作用下从处理的材料中浸出至与其他配制剂相比显著更小的程度。此外,未观察到例如常常用常规配制剂发生的活性成分与其他配制剂组分或其他活性成分的相互作用。此外,通过基质或环境,例如介质的pH或UV辐射的作用,活性成分的分解减慢或甚至完全停止。令人惊讶的是,未观察到活性成分通过掺入聚合物基质中的降低的效率。
本发明还涉及一种用于保护木质纤维素材料,尤其是木材以防有害昆虫,尤其是上述木材破坏性昆虫侵袭的方法。该方法包括用本发明含水杀虫剂组合物和/或用从中制备的粉状杀虫剂组合物处理木质纤维素材料。
除木材和下游产品如木材半成品、胶合板、粗纸板、MDF板或OSB板外,木质纤维素材料还有造纸中的木浆和中间物、基于木质纤维素的织物如棉,基于木质一年生植物的材料,例如油菜屑形成的模制品、bargasse板、稻草板及类似物。此外,木质纤维材料包括木质纤维纤维材料形成的制品,例如织物、成型织物、纸、板、绝热材料、绳、缆等。适用于本发明方法的纤维材料包含纺织纤维,如亚麻、亚麻布、大麻、黄麻、棉和苎麻,纸纤维,如亚麻、亚麻布或大麻,竹纤维、构树和木质纤维素纤维,以及荨麻纤维、蕉麻、剑麻、洋麻和椰子纤维。
处理可以以本身已知的方式,取决于基质的类型,通过使用未稀释的本发明活性成分组合物或用水稀释过的本发明活性成分组合物喷雾、涂覆、浸或浸渍基质,或通过使用未稀释的本发明活性成分组合物或用水稀释过的本发明活性成分组合物淹没基质而进行。本发明组合物也可例如作为粘合剂或作为施胶剂存在于木质纤维素材料的生产中。
如果本发明基质为木材,则在木材防腐中使用例如由Ullmann’sEncyclopedia of Industrial Chemistry,Wood preservation,CD-ROM第5版,Wiley VCH,Weinheim,1997,第7章中已知的常规方法。这些尤其包括借助压差而用于浸渍木材的方法,例如真空-压力方法和双真空浸渍。
用本发明活性成分组合物处理这种材料可根据用于此的常规方法而进行,并且每种情况下将以本身已知的方式适应技术现实。就这点而言,施用浓度和掺入取决于材料的危险度和各个处理方法,通常为每kg材料0.05mg至10g的活性成分。
包含活性成分的未稀释的组合物常常作为助粘合剂例如与所用的粘合剂一起用于木材下游产品和木质纤维素材料。显然,生产期间或之后的分离处理,例如施胶也是可能的。
除提到的木质纤维基材料外,本发明含水活性成分组合物也可用于保护材料以防动物害虫侵染的其他领域。例如,皮肤、毛皮或皮革可用本发明含水组合物或从中产生的粉末有效保护而不受动物害虫侵染。
如下实施例意欲阐明本发明,而并非限制本发明:
实施例1:分散体D1和D2
通用制备程序:
将465g去离子水、5重量%进料1和10重量%进料2在80℃下加热。10分钟后,开始加入其余进料1和2。进料时间为3.5小时。进料已结束后,在80℃下保持混合物另外30分钟,然后冷却至室温。
进料1:
496.1g去离子水
7.6g硫酸(50重量%)
361.0g甲基丙烯酸甲酯
19.0g甲基丙烯酸二甲基氨基乙基酯
57.0g乳化剂溶液E1
xg活性成分(见表1)
进料2:
1.5g2,2′-偶氮二(N,N′-二甲基异丁基脒)在63.3g去离子水中的溶液
乳化剂溶液E1:40重量%浓度的通过硬脂胺用4-5摩尔氧化乙烯连续乙氧基化,其后用硫酸二甲酯季铵化而得到的阳离子乳化剂的水溶液。
表1
分散体 | 活性成分 | x[g] |
D1 | 氟唑虫清 | 5 |
D2 | α-氯氰菊酯 | 65 |
产生的分散体的固体含量为约29.5重量%,粘度为100mPa·s。聚合物的玻璃化转变温度为87℃,其通过DSC方法测定。平均粒度为157-175nm,其通过光散射方法测定。
实施例2:分散体D3和D4
通用制备程序:
将465g去离子水、进料1和10重量%进料2在80℃下加热。10分钟后,开始加入其余进料2和进料3。进料2和进料3的进料时间为3.5小时。进料已结束后,在80℃下保持混合物另外30分钟,然后冷却至室温。
进料1:
46.1g去离子水
38.0g苯乙烯
7.6g3-(N,N)-二甲基氨基丙基甲基丙烯酰胺
14.2g乳化剂溶液E1(见上面)
进料2:
1.5g2,2′-偶氮二(N,N′-二甲基异丁基脒)在63.3g去离子水中的溶液
进料3:
450.1g去离子水
7.6g丙烯酸
270.0g甲基丙烯酸甲酯
57.0g甲基丙烯酸二甲基氨基乙基酯
42.8g乳化剂溶液E1(见上面)
x g活性成分(见表2)
表2
分散体 | 活性成分 | x[g] |
D3 | 氟唑虫清 | 61.8 |
D4 | α-氯氰菊酯 | 42.9 |
产生的分散体固体含量为约29.8重量%,粘度为105mPa·s。聚合物的玻璃化转变温度为110℃,其通过DSC方法测定。平均粒度为155-175nm,其通过光散射方法测定。
实施例3:分散体D5
将226g去离子水、5重量%进料1和10重量%进料2在80℃下加热。10分钟后,开始加入其余进料1和2。进料时间为3.5小时。进料已结束后,在80℃下保持混合物另外30分钟,然后冷却至室温。
进料1:
140.0g去离子水
3.0gH2SO4
22.5g乳化剂溶液E1
30.0g苯乙烯
112.5g甲基丙烯酸甲酯
7.5g甲基丙烯酸二甲基氨基乙基酯
21.71gα-氯氰菊酯
进料2:0.6g2,2′-偶氮二(N,N′-二甲基异丁基脒)在25g水中
产生的分散体的固体含量为约28.7重量%,粘度为100mPa·s。聚合物的玻璃化转变温度为78.3℃,其通过DSC方法测定。通过光散射方法测定的平均粒度为107nm。
参考例:阴离子分散体D6(不根据本发明)
将577g去离子水、5重量%进料1和10重量%进料2在80℃下加热。10分钟后,开始加入其余进料1和2。进料时间为3.5小时。进料已结束后,在80℃下保持混合物另外30分钟,然后冷却至室温。
进料1:
420.0g水
31.3g乳化剂E2
23.5g甲基丙烯酸
446.5g甲基丙烯酸甲酯
14.1gα-氯氰菊酯
进料2:75.2g2.5重量%浓度的过硫酸钠在水中的溶液
乳化剂E2:乙氧基化C12-14链烷醇的硫酸单酯的钠盐(乙氧基化度:30)
产生的分散体的固体含量为约29.8重量%,粘度为100mPa·s。聚合物的玻璃化转变温度为122.7℃,其通过DSC方法测定。平均粒度为178nm,其通过光散射方法测定。
实施例4:分散体D7-D16
聚合物水分散体D7-D16类似于实施例2而制备,进料1和进料3的单体组成示于表3。在所有情况下,进料1中的单体与进料3中的单体的重量比为4∶6。在所有情况下,进料3包含基于进料3中存在的单体9pphmα-氯氰菊酯。在分散体D9中,进料1额外包含基于进料1中存在的单体5pphmα-氯氰菊酯。
表3
1)pphm:基于存在于进料中的单体的重量百分比
MMA:甲基丙烯酸甲酯
BDGA:二丙烯酸丁基乙二醇酯
AMA:甲基丙烯酸烯丙基酯
DMAEMA:甲基丙烯酸二甲基氨基乙基酯
所有分散体的平均粒度为100nm以下。分散体D12、D13和D14呈芯-壳形态,壳含苯乙烯(在甲基丙烯酸丁酯基质中通过透射电子显微镜和RuO4反衬方法测定)。所有其他分散体呈所谓的黑莓形态。
应用计算:
杀虫活性:
组合物的杀虫作用通过如下实验证实:
将实施例3的本发明含水活性成分组合物用水稀释至三种不同的活性成分浓度。为了比较,研究非本发明的阴离子分散体D6,将α-氯氰菊酯溶于丙酮中,将溶液用另外的丙酮稀释以得到所述活性成分浓度。
为测定本发明组合物关于木材破坏性地下白蚁(Reticulitermessantonensis)的效力限度,将规格为25×25×6mm3的松属(Pinus spp.)木材试样(南方黄松)在根据DIN EN 84:1997-01(就这点而言,见“acceleratedaging of treated timber before biological tests”,European standardizationcommittee)浸出(leaching)后在约束实验条件下根据美国试验标准AWPAE1-97(就这点而言,见“Standard method for laboratory evaluation todetermine resistance to subterranean termites”,AmericanWood-Preservers’Association,2001)进行试验。
试验4周后,通过如AWPA E1-97规定,对木材试样视觉上评分而记录由白蚁侵袭所引起的木材破坏。另外估算白蚁中的死亡率。
如果木材试样仍无损伤(等级10-0上评分为10-9“坚固-轻度侵袭(sound-light attack)”),则通过特定活性成分浓度下的防腐剂而得到的木材保护认为是足够的。
对于本发明活性成分组合物的含水阳离子设计,测定浸出后对于α-氯氰菊酯的限度为≥20g/m3。木材在该最小浓度下得到有效保护(在现有情况下评分为10“坚固,允许表面轻咬”的)。浸出后对于溶于纯丙酮中用于比较目的的活性成分,限度为29-40g/m3(见表3)。
表3:
在实践条件下的木材防腐剂的评定尤其依靠浸出后的上限值。表3中显示的结果证实本发明活性成分组合物D5的阳离子设计具有比配制剂D6相应阴离子设计或有机溶剂中的纯活性成分更好的对抗木材破坏性地下白蚁的活性。
Claims (13)
1.一种细碎聚合物粒子的水分散体形式的杀虫剂组合物,其中细碎聚合物粒子包含至少一种在25℃,1013毫巴下在水中溶解度为不大于5g/l的杀虫有机活性成分且通过动态光散射测定平均粒度为不大于500nm,其中包含至少一种杀虫活性成分的聚合物粒子具有正表面电荷且其中包含活性成分的聚合物粒子的水分散体通过使烯属不饱和单体M的单体组合物经受自由基水乳液聚合而得到,其中烯属不饱和单体M包含至少一种溶解形式的上述杀虫有机活性成分,其中所述单体M包含基于单体M的总量,0.1-20重量%至少一种单烯属不饱和单体M-k,其中所述单体M-k选自通式I的单体:
其中
R1为氢或C1-C4烷基,
R2、R3各自独立地为C1-C4烷基,以及
R4为氢或C1-C4烷基,
Y代表氧、NH或NR5,其中R5=C1-C4烷基,
A代表任选间隔1、2或3个非相邻氧原子的C2-C8亚烷基,以及
X-代表阴离子同等物,
以及,如果R4=H,式I的单体的游离碱;
其中所述单体M包含基于单体M的总量,60-99重量%至少一种在25℃下在水中溶解度不大于60g/l的中性单烯属不饱和单体M1,所述单体M1选自乙烯基芳族单体、丙烯酸C2-C10烷基酯和甲基丙烯酸C1-C10烷基酯,其中所述包含活性成分的聚合物粒子的水分散体通过单体组合物在阳离子表面活性物质的存在下自由基水乳液聚合而得到,
并且所述杀虫剂组合物以基于用于制备聚合物的单体M的重量,0.5-30重量%的量包含至少一种所述杀虫有机活性成分。
2.根据权利要求1的杀虫剂组合物,其中所述阳离子表面活性物质基于待聚合的单体M的总量以0.2-12重量%的量使用。
3.根据权利要求1或2的杀虫剂组合物,其中所述聚合物的玻璃化转变温度Tg为至少10℃,其中所述玻璃化转变温度Tg为根据ASTM D3418-82通过差示扫描量热法测定的中点温度。
4.根据权利要求1或2的杀虫剂组合物,其中所述杀虫活性成分选自合成除虫菊酯类、氨基甲酸酯类、有机(硫代)磷酸酯类、节肢动物生长调节剂、氟唑虫清和新烟碱类。
5.根据权利要求1或2的杀虫剂组合物,其中所述聚合物粒子包含至少一种杀虫活性成分作为唯一活性成分。
6.根据权利要求1或2的杀虫剂组合物,其中挥发性有机组分基于组合物总重量为小于1重量%,其中所述挥发性组分为在大气压力下沸点为200℃以下的所有有机化合物。
7.根据权利要求1或2的杀虫剂组合物,其中固体含量为10-60重量%。
8.制备根据权利要求1-7中任一项的杀虫剂组合物的方法,其包括烯属不饱和单体M的单体组合物的自由基水乳液聚合,其中烯属不饱和单体M包含至少一种溶解形式的所述杀虫有机活性成分。
9.一种通过将根据权利要求1-7中任一项的含水杀虫剂组合物干燥而得到的粉状杀虫剂组合物。
10.根据权利要求1-7中任一项的含水杀虫剂组合物或根据权利要求9的粉状杀虫剂组合物在防治木材破坏性昆虫中的用途。
11.根据权利要求1-7中任一项的含水杀虫剂组合物或根据权利要求9的粉状杀虫剂组合物在保护木质纤维素材料免受有害昆虫侵袭中的用途。
12.一种保护木质纤维素材料免受有害昆虫侵袭或破坏的方法,其包括用根据权利要求1-7中任一项的含水杀虫剂组合物和/或用根据权利要求9的粉状杀虫剂组合物处理木质纤维素材料。
13.根据权利要求12的方法,其中所述木质纤维素材料为木材。
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ES (1) | ES2538033T3 (zh) |
IL (1) | IL185782A0 (zh) |
MX (1) | MX2007010607A (zh) |
NZ (1) | NZ561054A (zh) |
PT (1) | PT1860938E (zh) |
UA (1) | UA85790C2 (zh) |
WO (1) | WO2006094792A1 (zh) |
ZA (1) | ZA200708554B (zh) |
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JP2007137807A (ja) * | 2005-11-16 | 2007-06-07 | Nippon Nohyaku Co Ltd | 白蟻類防除組成物及び防除方法 |
EP2319307A3 (de) | 2008-05-21 | 2011-08-31 | Bayer CropScience AG | Insektizide Zusammensetzungen zur Behandlung von alkalischen Oberflächen mit verbesserter Langzeitwirkung |
TWI468109B (zh) * | 2008-06-16 | 2015-01-11 | Bayer Cropscience Ag | 具有改良的於表面上長效活性之殺昆蟲調配物 |
CN104960064B (zh) * | 2008-07-25 | 2018-08-10 | 巴斯夫欧洲公司 | 木质纤维产品及其制备方法 |
EP2183969A3 (en) * | 2008-10-29 | 2011-01-05 | Basf Se | Method for increasing the number of seedlings per number of sowed grains of seed |
WO2010147936A1 (en) * | 2009-06-16 | 2010-12-23 | Huntsman International Llc | Release compositions for lignocellulosic composites |
AU2011271403B2 (en) * | 2010-06-07 | 2016-12-22 | Syngenta Participations Ag | Stabilized chemical composition |
US20130078297A1 (en) | 2010-06-16 | 2013-03-28 | Basf Se | Aqueous Active Ingredient Composition |
CN103313598A (zh) * | 2010-07-02 | 2013-09-18 | 拜耳知识产权有限责任公司 | 农药组合物 |
CN104039140B (zh) | 2011-08-23 | 2017-07-21 | 维弗作物保护公司 | 拟除虫菊酯配制品 |
GB201119139D0 (en) * | 2011-11-04 | 2011-12-21 | Arch Timber Protection Ltd | Additives for use in wood preservation |
JP6062454B2 (ja) * | 2011-12-22 | 2017-01-18 | ヴァイヴ クロップ プロテクション インコーポレイテッドVive Crop Protection Inc. | ストロビルリン配合物 |
WO2014053410A1 (de) * | 2012-10-05 | 2014-04-10 | Basf Se | Herstellung wässriger polymerdispersionen mit schutzkolloiden im monomerzulaufverfahren |
JP2015221892A (ja) * | 2014-04-30 | 2015-12-10 | 大阪ガスケミカル株式会社 | 粒子 |
NZ772669A (en) | 2014-05-02 | 2023-12-22 | Arch Wood Protection Inc | Wood preservative composition |
FR3028043B1 (fr) * | 2014-10-31 | 2016-12-09 | Centre Scient Et Technique Du Batiment (Cstb) | Procede de detection d'une contamination a la merule |
EP3325464B1 (en) | 2015-07-24 | 2022-04-20 | Basf Se | Pyridine compounds useful for combating phytopathogenic fungi |
EA201890627A3 (ru) | 2015-09-03 | 2021-11-30 | Басф Агро Б.В. | Гербицидная композиция микрочастиц, включающая сафлуфенацил, способ ее получения и ее применение |
WO2019038642A1 (en) | 2017-08-25 | 2019-02-28 | Vive Crop Protection Inc. | MULTI-COMPONENT PESTICIDE COMPOSITIONS APPLIED TO SOIL |
CN108586279A (zh) * | 2018-06-26 | 2018-09-28 | 上海泰禾国际贸易有限公司 | 一种间二酰胺类化合物及其制备方法和应用 |
CN113365497A (zh) * | 2018-12-18 | 2021-09-07 | 拜耳公司 | 用于病媒防治和害虫防治的具有提高的接触功效的杀虫制剂 |
EP4011208A1 (en) | 2020-12-08 | 2022-06-15 | BASF Corporation | Microparticle compositions comprising fluopyram |
EP4011205A1 (en) | 2020-12-08 | 2022-06-15 | Basf Se | Microparticle compositions comprising trifludimoxazin |
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- 2006-03-08 PT PT67232975T patent/PT1860938E/pt unknown
- 2006-03-08 WO PCT/EP2006/002143 patent/WO2006094792A1/de active Application Filing
- 2006-03-08 MX MX2007010607A patent/MX2007010607A/es active IP Right Grant
- 2006-03-08 EA EA200701821A patent/EA012040B1/ru not_active IP Right Cessation
- 2006-03-08 AU AU2006222169A patent/AU2006222169B2/en not_active Ceased
- 2006-03-08 KR KR1020077022929A patent/KR101311019B1/ko active IP Right Grant
- 2006-03-08 AR ARP060100877A patent/AR053028A1/es unknown
- 2006-03-08 UA UAA200711107A patent/UA85790C2/ru unknown
- 2006-03-08 BR BRPI0609026A patent/BRPI0609026B1/pt not_active IP Right Cessation
- 2006-03-08 ES ES06723297.5T patent/ES2538033T3/es active Active
- 2006-03-08 US US11/885,799 patent/US8999358B2/en active Active
- 2006-03-08 EP EP06723297.5A patent/EP1860938B1/de active Active
- 2006-03-08 JP JP2008500121A patent/JP4966293B2/ja not_active Expired - Fee Related
- 2006-03-08 CA CA002599507A patent/CA2599507A1/en not_active Abandoned
- 2006-03-08 CN CN2006800157177A patent/CN101170902B/zh not_active Expired - Fee Related
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2007
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Also Published As
Publication number | Publication date |
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BRPI0609026B1 (pt) | 2015-11-24 |
US8999358B2 (en) | 2015-04-07 |
BRPI0609026A2 (pt) | 2010-11-16 |
AU2006222169A1 (en) | 2006-09-14 |
MX2007010607A (es) | 2007-10-18 |
EP1860938A1 (de) | 2007-12-05 |
IL185782A0 (en) | 2008-01-06 |
JP2008532965A (ja) | 2008-08-21 |
ZA200708554B (en) | 2009-04-29 |
US20080138371A1 (en) | 2008-06-12 |
CN101170902A (zh) | 2008-04-30 |
AR053028A1 (es) | 2007-04-18 |
KR101311019B1 (ko) | 2013-09-24 |
JP4966293B2 (ja) | 2012-07-04 |
PT1860938E (pt) | 2015-07-27 |
AU2006222169B2 (en) | 2012-01-12 |
CA2599507A1 (en) | 2006-09-14 |
KR20070118111A (ko) | 2007-12-13 |
ES2538033T3 (es) | 2015-06-16 |
UA85790C2 (ru) | 2009-02-25 |
NZ561054A (en) | 2011-03-31 |
EA012040B1 (ru) | 2009-06-30 |
EA200701821A1 (ru) | 2008-02-28 |
WO2006094792A1 (de) | 2006-09-14 |
EP1860938B1 (de) | 2015-05-13 |
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