CN1627900A - 含有三唑和烷氧化胺的制剂 - Google Patents
含有三唑和烷氧化胺的制剂 Download PDFInfo
- Publication number
- CN1627900A CN1627900A CNA038032716A CN03803271A CN1627900A CN 1627900 A CN1627900 A CN 1627900A CN A038032716 A CNA038032716 A CN A038032716A CN 03803271 A CN03803271 A CN 03803271A CN 1627900 A CN1627900 A CN 1627900A
- Authority
- CN
- China
- Prior art keywords
- composition
- azoles
- alkoxylated amines
- formula
- propiconazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001412 amines Chemical class 0.000 title claims abstract description 40
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- 239000005822 Propiconazole Substances 0.000 claims description 29
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 27
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- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及使用烷氧化胺提高含有杀真菌三唑的杀菌制剂的活性。本发明还涉及包含一或多种杀真菌三唑和烷氧化胺的制剂。上述制剂可用来保护各种有生命或无生命的材料:如作物、植物、果实、种子、木制品、建材等、生物可降解材料和纺织品不受真菌作用的损害。
Description
本发明涉及使用烷氧化胺提高含有杀真菌三唑的杀菌制剂的活性。本发明还涉及包含一或多种杀真菌三唑和烷氧化胺的制剂。上述制剂可用来保护各种有生命或无生命的材料:如作物、植物、果实、种子、木制品、建材等、生物可降解材料和纺织品不受真菌作用的损害。
已知许多种类的化合物可作为杀微生物且特别是杀真菌化合物。在上述类别中杀真菌三唑类特别有价值,而且目前,其中的几种化合物被广泛地用作杀微生物剂,特别是杀真菌剂。
一些木材防腐剂被公开于EP-0,393,746,其中公开了用于保护木材、木制品和生物降解材料不受真菌侵扰和损害的戊唑醇和丙环唑的增效组合物。WO-96/10332公开的液体木材防腐制剂包含通过铜离子和烷氧化二胺反应形成的配合物。JP-60-051102和JP-61-151102公开了使用烷氧化胺和二胺稳定含有1H-1,2,4-三唑-1-乙亚胺基硫代酸,如酰胺唑的杀真菌制剂。
杀真菌剂三唑本身作为单一的活性成分,无法提供对抗各种真菌、细菌、和其它微生物以保护各种有生命或无生命的材料:如作物、植物、果实、种子、木制品、建材等、生物可降解材料和纺织品不受损害。
令人惊奇的是,现已发现通过加入式(I)的烷氧化胺,明显提高了包含杀真菌三唑的制剂的效果。因此本发明的杀真菌制剂包含一或多种杀真菌三唑和提高效果或性能的式(I)烷氧化胺,和载体。
根据本发明的一个方面提供的杀真菌组合物包含,在本领域技术人员容易确定的一些宽范围限定的组合物中(即:在各自一定比例或量的活性成分中),以增效比例组合的一或多种杀真菌三唑加上式(I)的烷氧化胺,和一种载体。
杀真菌三唑包括:
戊环唑 1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]甲基]-1H-1,2,4-三唑,
糠菌唑 1-[[4-溴-2-(2,4-二氯苯基)四氢-2-呋喃基]甲基]-1H-1,2,4-三唑,
环唑醇 α-(4-氯苯基)-α-(1-环丙基乙基)-1H-1,2,4-三唑-1-乙醇,
噁醚唑 1-[[2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基]甲基]-1H-1,2,4-三唑,
氧唑菌 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-1-乙醇,
腈苯唑 α-[2-(4-氯苯基)乙基]-α-苯基-1H-1,2,4-三唑-1-丙腈,
喹唑菌酮 3-(2,4-二氯苯基)-6-氟-2-(1H-1,2,4-三唑-1-基)-4-(3H)-喹唑啉酮,
氟硅唑 1-[[双(4-氟苯基)甲基甲硅烷基]-甲基]-1H-1,2,4-三唑,
己唑醇 α-丁基-α-(2,4-二氯苯基)-1H-1,2,4-三唑-1-乙醇,
ketoconazole 1-乙酰基-4-[4-[[(2R,4S)-2-(2,4-二氯苯基)-2-(1H-咪唑-1-基甲基)-1,3-二氧戊环-4-基]甲氧基]苯基]-哌嗪,
环戊唑菌 5-[(4-氯苯基)甲基]-2,2-二甲基-1-(1H-1,2,4-三唑-1-基甲基)-环戊醇,
戊菌唑 1-[2-(2,4-二氯苯基)戊基]-1H-1,2,4-三唑,
丙环唑 1-[[2-(2,4-二氯苯基)-4-丙基-1,3-二氧戊环-2-基]甲基]-1H-1,2,4-三唑,
戊唑醇 α-[2-(4-氯苯基)乙基]-α-(1,1-二甲基乙基)-1H-1,2,4-三唑-1-乙醇,
氟醚唑 1-[2-(2,4-二氯苯基)-3-(1,1,2,2-四氟乙氧基)丙基]-1H-1,2,4-三唑,
戊叉唑醇 5-[(4-氯苯基)甲基烯基]-2,2-二甲基-1-(-1H-1,2,4-三唑-1-乙醇,
根据本发明的组合物还可含有多于一种的三唑化合物,例如,其可包含两或多种选自戊环唑、丙环唑、环唑醇、氟硅唑、和戊唑醇的三唑,或环唑醇和丙环唑的混合物,或戊唑醇、丙环唑和环唑醇的混合物。
杀真菌三唑可以其碱形式或盐形式存在,后者可通过其碱与适合的酸反应制备。适合的酸例如包含:无机酸,如氢卤酸,即氢氟酸、氢氯酸、氢溴酸和氢碘酸,硫酸、硝酸、磷酸,膦酸等;或有机酸,例如乙酸、丙酸、羟基乙酸、2-羟基丙酸、2-氧丙酸、乙二酸、丙二酸、丁二酸、(Z)-2-丁烯二酸、(E)-2-丁烯二酸、2-羟基丁二酸、2,3-二羟基丁二酸、2-羟基-1,2,3-丙三羧酸、甲磺酸、乙磺酸、苯磺酸、4-甲基苯磺酸、环己烷氨基磺酸、2-羟基苯甲酸、4-氨基-2-羟基苯甲酸等酸。
杀真菌三唑的盐还包含所述杀真菌三唑可以形成的金属配合物。其中之一的成分可以配合物存在而另一种不是配合物;或者所有的成分都以配合物存在。上述的金属配合物由一或多种活性成分的分子与一或多种有机或无机金属盐之间形成的配合物组成。所述的有机或无机盐的实例包含卤素、硝酸、硫酸、磷酸、乙酸、三氟乙酸、三氯乙酸、丙酸、酒石酸、磺酸,例如甲基磺酸、4-甲基苯基磺酸、水杨酸、苯甲酸等的元素周期表中第二主族金属,例如镁或钙盐,第三或第四主族,例如铝、锡、铅以及元素周期表中第一至第八过渡组金属,例如铬、锰、铁、钴、镍、铜、锌等的盐。优选的金属是属于第四过渡组的金属。金属可以以其各自可能的价态存在。金属离子可以以其任何可能的价态存在,对于最优选的金属铜,最优选以其二价形式Cu(II)使用。适合的铜化合物是硫酸铜、乙酸铜、氢氧化铜、氧化铜、硼酸铜、氟化铜以及特别是碱式碳酸铜Cu(OH)2CuCO3。配合物可以是单-或多核的,它们可以包含一或多个有机分子部分作为配位体。
当使用术语“杀真菌三唑”时,其意味者包括所述化合物的碱或其盐形式,后者可通过其碱与适合的酸反应制备。在本文中使用的术语盐还包含杀真菌三唑可能形成的溶剂化物。上述溶剂化物的实例例如:水合物、醇化物等。
为了达到安全地防治真菌的目的,在本发明组合物中使用的杀真菌三唑,优选以其基本上纯化的形式存在,即应从制备和/或处理方法中除去化学不纯物(如共生产物或残留的溶剂)。术语“基本上纯化”意为通过本领域常规方法如高效液相色谱测定的化学纯,至少为96%,优选至少98%且更优选至少99%。
式(I)的烷氧化胺具有下述的通式
其中
R1为C8-20烷基;
R2为-[CH2CH(X)O]bH (a-1)
或
n为1至4的整数;
每个a,b和c各自独立地为1至20的整数;
每个X各自独立地选自由氢、甲基、乙基、和苯基组成的基团。
令人感兴趣的一组式(I)化合物是其中a,b和c各自独立地为1至6整数的式(I)化合物。
第一组具体的式(I)烷氧化胺是其中R2代表(a-1)基团的式(I)化合物。
第二组具体的式(I)烷氧化胺是其中R2代表(a-2)基团的式(I)化合物。
更具体的式(I)烷氧化胺是带有一或多种下述限定的式(I)烷氧化胺:
a)n为2或3的整数,优选n为3;
b)X为氢;
c)R为C10-20烷基,优选椰子烷基或牛脂烷基。
下述表中例示了优选的式(I)烷氧化胺:
产品名 | 化学名 | CAS号 |
PropoduomeenC/13 | N,N’,N’-三(2-羟基丙基)-N-椰子烷基-1,3-二氨基丙烷 | |
Ethoduomeen T/11 | 单-(2-羟基乙基)-N-牛脂烷基-1,3-二氨基丙烷 | 61790-85-0 |
Ethoduomeen T/13 | N,N’,N’-三(2-羟基乙基)-N-牛脂烷基-1,3-二氨基丙烷 | 90367-27-4 |
Ethoduomeen T/25 | N,N’,N’-聚氧乙烯(15)-N-牛脂烷基-1,3-二氨基丙烷 | 61970-85-0 |
Ethoduomeen C/13 | N,N’,N’-三(2-羟基乙基)-N-椰子烷基-1,3-二氨基-丙烷 | 90367-21-8 |
最优选的式(I)烷氧化胺为N,N’,N’-三(2-羟基乙基)-N-椰子烷基-1,3-二氨基-丙烷。
在具体的杀真菌组合物中的一或多种杀真菌三唑和式(I)的烷氧化胺的相对比例,是与组合物包括的活性成分,即一或多种单独的杀真菌三唑或单独的式(I)的烷氧化胺相比,对真菌能够得到不可预期的提高的效果,优选增效的比例。本领域技术人员容易理解的是,所述的提高效果,是根据测定的对某种真菌的效果和被处理的物质,通过各种比例的一或多种杀真菌三唑和式(I)的烷氧化胺的杀真菌组合物得到的。可是,通常,对所有真菌的来讲,一或多种杀真菌三唑与式(I)的烷氧化胺在活性组合物中适合的重量比例在5∶1至1∶200,适合地从5∶1至1∶50,优选2∶1至1∶20,更优选1∶1至1∶10。杀真菌三唑与式(I)的烷氧化胺的具体比例(w/w)为1∶160、1∶80、1∶40、1∶20、1∶10和1∶5。
在本发明组合物中每种活性成分的量,即一或多种杀真菌三唑和烷氧化胺的量是能够获得有效杀真菌效果的量。特别的预期在本发明现用组合物中包含0.01%(w/v)至10%(w/v),优选0.1%(w/v)至1.5%(w/v)的一或多种杀真菌三唑。在现用组合物中的式(I)烷氧化胺以0.1%(w/v)至40%(w/v),优选0.5%(w/v)至10%(w/v)存在。所述的现用组合物的制备是通过用适当的稀释剂,如水稀释浓缩组合物。
本发明组合物对保护的植物、特别是栽培植物具有良好的治疗、保护和系统的杀真菌活性。本发明组合物可用来保护被微生物侵染、损害的植物或植物部分,例如果实、花蕾、花、叶、茎、根,植物或栽培植物的块茎,由此保护植物后期的生长部分不受上述微生物的影响。
本发明组合物具有系统活性。它们还可用于种子消毒(果实、块茎、谷物颗粒)和处理植物插枝以及消灭存在在土壤中的致病真菌。本发明组合物特别有价值的是其良好的植物耐受性和较少的环境问题(低使用剂量)。
根据本发明的杀真菌组合物可使用到的多种栽培植物的实例,其名称例如谷物,如小麦、大麦、黑麦、燕麦、水稻、高梁等;甜菜,例如糖甜菜和伺用甜菜;梨果和坚果和浆果,例如苹果、梨、李子、桃、柠檬、樱桃、草莓、木莓和黑莓;豆科植物,例如菜豆、小扁豆、豌豆、大豆;油料植物,例如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可、花生;葫芦科植物,例如南瓜、小黄瓜、瓜、黄瓜、西葫芦;纤维植物,例如棉花、亚麻、大麻、黄麻;柑桔类果实,例如柑桔、柠檬、柚子、中国柑桔;蔬菜,例如菠菜、莴苣、芦笋、十字花科蔬菜如甘蓝和芜菁、胡萝卜、洋葱、番茄、马铃薯、辣椒和甜椒;月桂属植物,例如鳄梨、肉桂、樟脑;或植物如玉米、烟草、坚果、咖啡、甘蔗、茶、葡萄、啤酒花、香蕉、橡胶,以及观赏植物,例如花、灌木、每年落叶树和长绿树如松。列举上述栽培植物的目的是为了例示本发明而不是为了限制本发明。
给药本发明杀真菌组合物的具体方式是向植物的地上部分、特别是其叶部给药(叶面使用)。使用的次数和给药的剂量是根据病原生活的生物特性和气候条件选择的。而且杀真菌组合物还可使用到土壤并通过根系统被植物吸收(系统活性),在这种情况下,是向植物的生长地喷洒液体组合物,或如果是固体制剂例如:颗粒制剂,可以将活性成分加入到土壤中(土壤使用)。
本发明的组合物特别适用于在收获后处理果实,特别是处理柑桔果实。在后者的情况下,可以向果实喷雾或在液体组合物中浸沾或浸渍果实,或者用蜡组合物包覆果实。后者的蜡组合物通常是通过混合胶悬剂和适合的蜡制备。用于喷雾、浸沾或浸渍使用的组合物的制备是通过用水介质稀释浓缩物,例如:乳油、胶悬剂或液剂。上述浓缩物一般都由活性成分、分散剂或悬浮剂(表面活性剂)、增稠剂、少量的有机溶剂、湿润剂、可选择的一些防冻剂,以及水组成。
本发明的杀真菌组合物还可用于保护种子防治真菌。为了获得上述效果可用本杀真菌组合物作为种子包衣剂包覆种子,此时用活性成分的液体组合物将种子植物的种子连续的浸渍,或如果需要包衣用事先混合的组合物包衣。
本发明杀真菌组合物可用于木材、木制品、以及生物可降解材料的保存并保护所述的材料防止真菌的攻击或损害。可用本发明杀真菌组合物保存的木材或木制品例如可以考虑:木制品如木料、木材、枕木、电话线杆、栏杆、木遮盖物、织编工艺、窗户和门、夹板、创花板、薄板、硬纸板、细木工制品、用在暴露在地上环境的木材如甲板和用于接触地面或淡水或海水环境的木材,桥梁或通常在室内、建筑物和木工业使用的木材。除了木材外可从用本发明制剂处理获益的可生物降解材料包括纤维材料如棉花。以及,皮革、纺织材料以及甚至于合成纤维、粗麻布、绳子和绳索。
保护木材不被沾污、褪色和腐烂意味者避免其霉变、腐烂、失去其可利用的机械性能如断裂强度、抗震性和剪应力,或由于出现气味、被沾污和形成斑点而损坏其外观或其它有用的性质。上述现象是由一些微生物引起的,下述为其典型的实例:
使木材褪色的真菌:
1:子囊菌:喙球菌(Ceratocystis),例如小喙球菌(Ceratocystisminor)
短柄霉(Aureobasidium),例如出芽短柄霉(Aureobasidiumpullulans)
Sclerophoma,例如Sclerophoma pithyophila
枝孢属(Cladosporium),例如腊叶枝孢(Cladosporiumherbarum)
2:半知菌:fungi imperfecti
曲霉属(Aspergillus),例如黑色曲霉(Aspergillus niger)Dactylium,例如Dactylium fusarioides
青霉属(Penicillium),例如短茎青霉(P.brecicaule),变幻青霉(P.variabile),绳状青霉(P.funiculosum)或绿青霉(P.glaucum)
Scopularia,例如Scopularia phycomyces
木霉(Trichoderma),例如绿色木霉(Trichoderma viride)或木质素木霉(Trichoderma lignorum)
链格孢属(Alternaria),例如纤细链格孢(Alternariatenius),互格链格孢(Alternaria alternata)
3:接合菌:毛霉(Mucor),例如刺囊毛霉(Mucor spinorus)。
使木材损坏的真菌:
1:软腐真菌:毛壳霉属(Chaetomium),例如球毛壳霉(Ch.globosum)或Ch.alba-arenulum
腐质霉属(Humicola),例如灰色腐质霉(Humicola grisea)
Petriella,例如Petriella setifera
毛束霉属(Trichurus),例如Trichurus spiralis
2:白色和棕色斑点真菌:
粉孢革菌属(Coniophora),例如单纯粉孢革菌(Coniophoraputeana)
革盖菌属(Coriolus),例如杂色革盖菌(Coriolus versicolor)
Donkioporia),例如Donkioporia expansa
蜂窝孢子菌属(Glenospora),例如Glenospora graphii
粘褶菌属(Gloeophyllum),例如冷杉粘褶菌(Gl.abietinum),
Gl.adiratum,Gl.protactum,Gl.sepiarium,窑粘褶菌(Gl.trabeum)
香菇属(Lentinus),例如浅杯状香菇(L.cyathiformes),埃杜香菇
(L.edodes),洁丽香菇(L.lepideus),L.grinus,或L.squarrolosus
Paxillus,例如Paxillus panyoides
灰侧耳菌属(Pleurotus),例如Pleurotus ostreatus,
卧孔菌属(Poria),例如P.monticola,P.placenta,凡伦梯式卧孔菌(P.vailllantii)或绵腐卧孔菌(P.vaporaria)
Serpula(Merulius),例如Serpula himantoides或Serpulacrymans
韧革菌属(Stereum),例如毛韧革菌(Stereum hirsutum)
Trychophyton,例如Trychophyton mentagrophytes
Tyromeces,例如tyromeces palustris
为了保护木材不腐烂,可用本发明的杀真菌组合物处理木材。上述处理以几种不同的方法进行如,例如在封闭加压或真空系统、在热或浸沾系统等处理木材,或使用本发明杀真菌组合物进行各种表面处理,例如喷雾、弥雾、喷粉、扩散、泼浇、刷涂、浸沾、浸泡或灌输木材。
本发明提供了保护木材、木制品或可生物降解材料的方法,其中包含向所述木材、木制品或可生物降解材料使用包含一或多种杀真菌三唑、式(I)的烷氧化胺,和载体的杀真菌组合物。进一步的,本方法的其它方面是提供了保护木材、木制品或可生物降解材料的方法,其中包含向所述木材、木制品或可生物降解材料使用包含一或多种杀真菌三唑加上增效比例的式(I)的烷氧化胺,和载体的杀真菌组合物。
本发明的杀真菌组合物包含一或多种杀真菌三唑加上式(I)的烷氧化胺,和载体。上述载体是配制所述杀真菌组合物时,在不影响其杀真菌效果的同时,为了促进其使用/散布到被处理场所,例如通过溶解、分散、或混合所述组合物,和/或促进其保存、运输或处理的任何材料和物质。上述适合的载体可以是固体或液体或加压形成液体的气体,即,本发明的组合物适合以浓缩物、乳剂、液剂、颗粒剂、细粉剂、喷雾剂、气雾剂、片剂、或粉剂使用。在许多情况下本发明组合物可通过制备的浓缩物直接使用,如,例如乳油、胶悬剂、或可溶浓缩物,或使用水或有机介质的稀释液,上述浓缩物是本发明定义中主要使用的组合物。在使用前的喷雾器桶中,可将上述浓缩物稀释成为现用混合物。优选的本发明组合物将含有大约0.01至95%重量的一或多种杀真菌三唑加上式(I)烷氧化胺的组合物。更优选的,上述范围为0.1至90%重量。最优选的,根据为具体使用目的选择的制剂的类型,上述范围为1至80%重量。
乳油是包含一或多种杀真菌三唑加上式(I)烷氧化胺的液体、均匀的制剂,可将其用水稀释后以乳液形式使用。胶悬剂是在液体中活性成分稳定的悬浮液,在使用前可将其用水稀释。可溶浓缩物是液体、均匀的制剂,在用水稀释后可以活性成分的真溶液使用。
本发明的杀真菌组合物还可配制成为蜡状物,用于包覆或包衣,例如果实,特别是柑桔果实。
在本发明组合物中使用的适合的载体和助剂可以是固体或液体、而且是制剂领域已知的适合物质,如,例如天然或再生的矿物、溶剂、分散剂、表面活性剂、湿润剂、粘合剂、增稠剂、结合剂、肥料或防冻剂。
本发明杀真菌组合物可选择的还包含季铵盐如卤化三甲基烷基铵型季铵盐,例如氯化三甲基癸基铵、氯化三甲基十二烷基铵、氯化三甲基牛脂基铵、氯化三甲基油基铵;或二甲基烷基苄基铵型,例如氯化二甲基癸基苄基铵、氯化二甲基十二烷基苄基铵、氯化二甲基十六烷基苄基铵(一般称作“cetalkonium chloride”)、氯化二甲基十八烷基苄基铵、氯化二甲基椰子苄基铵、氯化二甲基牛脂苄基铵;和特别的氯化二甲基C8-18烷基苄基铵混合物,其通用名为“烷基苄基铵”;卤化二甲基二烷基铵,例如:氯化二甲基二辛基铵、氯化二甲基二癸基铵、氯化二甲基二十二烷基铵、氯化二甲基二椰子铵、氯化二甲基二牛脂铵、氯化二甲基辛基癸基铵、氯化二甲基十二烷基辛基铵、氯化二甲基二氢化牛脂基铵。
例如为了扩大活性谱或防止出现抗性,如已述的本发明杀真菌组合物还可包含其它活性成分,如杀真菌剂、杀细菌剂杀螨剂、杀线虫剂、杀虫剂或除草剂,特别是杀真菌剂。在许多情况下,其可获得增效作用,即,混合物的活性超过了单独成分的活性。
作为与本发明杀真菌制剂组合使用的杀生剂,可以考虑下述类别的产品:
杀真菌剂:
2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2,6-二-氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧]-苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧亚氨基[α-{邻-甲苯氧基}-邻-甲苯基]乙酸甲酯;2-苯基苯酚(OPP),艾敌吗啉(aldimorph),氨丙膦酸,敌菌灵,苯霜灵,麦锈灵,苯菌灵,乐杀螨,联苯,联苯三唑醇,灭瘟素,乙嘧酚磺酸酯,丁硫啶,多硫化钙,杀螟丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,硫杂灵、清菌脲,酯菌胺,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,二甲嘧酚,烯酰吗啉,敌螨普,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,敌菌酮,克瘟散,乙嘧酚,氯苯嘧啶醇,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,醋酸三苯基锡,羟基三苯锡,福美铁,嘧菌腙,氟啶胺,咯菌腈,氟氯菌核利,磺菌胺,氟酰胺,粉唑醇,灭菌丹,三乙膦酸铝,四氯苯酞,呋霜灵,拌种胺,双胍盐,六氯苯,噁霉灵,抑霉唑,双胍辛酸盐,异稻瘟净(IBP),异菌脲,稻瘟灵,春雷霉素,含铜制剂如:氢氧化铜、环烷酸铜、王铜、硫酸铜、氧化铜、喹啉酮和波尔多液,代森锰铜,代森锰锌,代森锰,嘧菌胺,灭锈胺,甲霜灵,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,福美镍,异丙消,氟苯嘧啶醇,呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,稻瘟酯,戊菌唑,氯瘟磷,多马霉素,哌丙灵,多抗霉素,咪鲜胺,腐霉利,霜霉威,丙森锌,吡菌磷,啶斑肟,嘧霉胺,咯喹酮,五氯硝基苯(PCNB),硫磺粉和硫制剂,叶枯酞,四氯硝基苯,噻菌灵,噻菌腈,甲基硫菌灵,福美双,甲基立枯磷,甲苯氟磺胺,三唑酮,三唑醇,咪唑嗪,水杨菌胺,十三吗啉,氟菌唑,嗪胺灵,有效霉素,乙烯菌核利,代森锌,福美锌,异噻唑-和苯并异噻唑酮衍生物如,例如1,2-苯并异噻唑酮(BIT);噁噻嗪如bethoxazin(即3-(苯并[b]噻-2-基)-5,6-二氢-1,4,2-噁噻嗪,4-氧化物);亚胺菌如腈嘧菌酯,叉氨苯酰胺,pyraclostrobin,亚胺菌,trifloxystrobin,和picoxystrobin。
杀细菌剂:
溴硝丙二醇,双氯酚,三氯甲基吡啶,福美镍,春雷霉素,辛噻酮,呋喃羧酸,土霉素,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素,虫螨腈,乙酰甲胺磷,氟丙菊酯,棉铃威,涕灭威,顺式氯氰菊酯,双甲脒,阿维菌素,AZ 60541,艾扎丁,谷硫磷A,谷硫磷M,三唑锡,苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,高效氟氯氰菊酯,联苯菊酯,仲丁威,brofenprox,溴硫磷A,合杀威,噻嗪酮,丁酮威,哒螨灵,硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,啶蜱脲,虱螨胺,chloethocarb,氯氧磷,毒虫畏,氟啶脲,氯甲硫磷,氟唑虫清,毒死蜱,甲基毒死蜱,顺式苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯,氯氟氰菊酯,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,甲基内吸磷,内吸磷硫赶式异构体,甲基内吸磷硫赶式异构体,丁醚脲,二嗪磷,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌恶磷,乙拌磷,敌瘟磷,伊维菌素,S-氰戊聚酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,苯线磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫磷,苯氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,氟虫腈,氟啶胺,氟环脲,氟氰戊菊酯,氟虫脲,氟丙苄醚,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,六六六,庚烯磷,氟铃脲,噻螨酮,吡虫啉,异稻瘟净,氯唑磷,异柳磷,异丙威,噁唑磷,伊维菌素,高效氯氟氰菊酯,虱螨脲,马拉硫磷,灭蚜磷,mervinphos,甲亚砜磷,四聚乙醛,虫螨畏,甲胺磷,杀扑磷,甲硫威,灭多威,速灭威,milbemectin,久效磷,moxidectin,二溴磷,NC184,吡虫清,烯啶虫胺,氧乐果,杀线威,亚砜磷,异砜磷,对硫磷A,甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,嘧啶磷,甲基嘧啶磷,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发硫磷,吡蚜酮,吡唑硫磷,哒嗪硫磷,反灭虫菊,除虫菊素,哒螨灵,嘧螨醚,吡丙醚,喹硫磷,虫酰肼,蔬果磷,硫线磷,氟硅菊酯,治螟磷,硫丙磷,虫酰肼,吡螨胺,嘧丙磷,氟苯脲,七氟菊酯,双硫磷,terbam,特丁硫磷,杀虫畏,thiafenox,thiamethoxam,硫双威,久效威,甲基乙拌磷,除线磷,苏云金杆菌,四溴菊酯,苯螨噻,三唑磷,triazuron,敌百虫,杀铃脲,混杀威,有效霉素,灭除威,灭杀威,己体氯氰菊酯。
与本发明杀真菌制剂组合使用的其它杀生剂,可以考虑下述类别的产品:苯酚衍生物如3,5-二氯苯酚,2,5-二氯苯酚,3,5-二溴苯酚,2,5-二溴苯酚,2,5-(或者3,5-)二氯-4-溴苯酚,3,4,5-三氯苯酚,氯化氢二苯基醚如,例如,2-羟基-3,2’4’-三氯二苯基醚,苯基苯酚,4-氯-2-苯基苯酚,4-氯-2-苄基苯酚,二氯苯,六氯苯;醛类如甲醛,戊二醛,水杨醛;醇类如苯氧基乙醇;抗微生物活性羧酸及其衍生物;有机金属化合物如三丁基锡化合物;碘化合物如碘递体、碘鎓化合物;单-、二-和多胺如十二烷基胺或1,10-二(正庚基)-1,10-二氨基癸烷;锍和鏻化合物;巯基化合物及其金属盐,碱金属和重金属盐如2-巯基吡啶-N-氧化物及其钠和锌盐,3-巯基哒嗪-2-氧化物,2-巯基喹喔啉-1-氧化物,2-巯基喹喔啉-二-N-氧化物,以及所述巯基化合物对称二硫化物;脲如三溴-或三氯对称二苯脲,二氯三氟甲基二苯基脲;三溴水杨苯胺;2-溴-2-硝基-1,3-二羟基丙烷;二氯苯并噁唑酮;和双氯苯双胍已烷。
下述实施例是为了例示本发明,并且不构成对本发明任何方面的限制。
实施例1:对担子菌纲改性的EN113试验的效果
对用烤箱干燥的欧洲赤松(Pinus sylvestris,509kg/m3)和山毛榉树(Fagus sylbatica,637kg/m3)的木块(40×15×5mm),用包含5%丙环唑和20%N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷的水稀释液处理。根据被处理木块吸收的所述水稀释液的量,确定活性成分的量,即丙环唑和N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷的量,并用g/cm3表示吸收的活性成分(g活性成分/m3)。
在促进微生物生长的培养条件下,将木块样品放置于与真菌接触下8周(单纯粉孢革菌和杂色革盖菌)。然后清除木块上附着的菌丝体,并用烤箱干燥后称重。用开始试验和试验结束时在烤箱中的干重的差别计算产品的效果,用毒性临界值表示。临界值按两种标准定义,一种对应于适度保护木材所需的最低浓度(重量损失少于3%),另一种对应于在系列使用中的下一个浓度,在该浓度下无法得到对木材的适度保护(重量损失大于3%)。
表1:含有5%丙环唑和20% N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷的制剂的临界值(g丙环唑/m3)。
真菌 | 单纯粉孢革菌 | 杂色革盖菌 |
临界值对照临界值* | 58-117188-373 | 105-220331-458 |
:制剂仅包含丙环唑作为活性成分
N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷的毒性临界值可在WO-96/10332的第10页表1中找到,而且根据木材和真菌的类型在10240g/cm3至21080g/cm3的范围内。
表2:制剂对2种单独担子菌的数据
丙环唑浓度(ppm) | 吸收桃木/松木(g a.i/m3) | 粉孢革菌损失重量(%) | 革盖菌损失重量(%) |
100200400600800 | 54/58105/117220/228328/360449/477 | 20.91.00.20.1-0.2 | 13.38.50.70.1-0.1 |
实施例2:对小麦作物的药害和小麦白粉病(Erisiphe graminis)
的杀真菌活性
试验模型:用供试溶液喷雾冬小麦,品种Corvus,直到溶液滴下。将被处理的植
物在温室中培养,并在干燥后用小麦白粉病的分生孢子撒粉。
供试溶液:1)通过稀释市售的丙环唑制剂“Tilt250EC”,直到获得包含8,16,20,和24ppm的丙环唑喷雾溶液而制备水溶液。
2)制备包含40,80,160,320,640,1280和2560ppm的N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷(即ethoduomeen C/13)的水溶液。
3)向8和16ppm丙环唑的水溶液中加入一定量的“ethoduomeenC/13”,获得其中丙环唑与“ethoduomeen C/13”的比例为1/160,1/80,1/40,1/20,1/10和1/5的供试溶液。
将包含25%(w/v)的丙环唑市售“Tilt250EC”制剂溶解在芳香石油烃液体混合物中。
撒粉17天后评价带有小麦白粉病的小麦植物上的真菌生长抑制率。
结果和结论
对照植物上的小麦白粉病侵染率是100%,用24ppm丙环唑处理的植物对小麦白粉病有80%的活性。
当试验与“ethoduomeen C/13”混合的丙环唑时,可以看到对小麦白粉病杀真菌活性的明显增加。
·16ppm丙环唑和“ethoduomeen C/13”以低至1/10的比例组合几乎具有完全的活性(98%),同时16ppm的丙环唑的活性为50%。
·8ppm丙环唑和“ethoduomeen C/13”以低至1/10的比例组合活性为大约80%,同时8ppm的丙环唑的活性为25%。
表3:在小麦上丙环唑/“ethoduomeen C/13”混合制剂对小麦白粉病的杀真菌活性。抑制%是4个重复的平均值。
化合物浓度(活性成分ppm) | 对小麦白粉病杀真菌活性% | ||
丙环唑 | Ethoduomeen C/13 | 比例 | |
24 | 0 | - | 80 |
20 | 0 | - | 50 |
16 | 0 | - | 50 |
8 | 0 | - | 25 |
0 | 2560 | - | 0 |
0 | 1280 | - | 0 |
0 | 640 | - | 0 |
0 | 320 | - | 0 |
0 | 16 | - | 0 |
0 | 80 | - | 0 |
0 | 40 | - | 0 |
16 | 2560 | 1/160 | 98 |
16 | 1280 | 1/80 | 98 |
16 | 640 | 1/40 | 98 |
16 | 320 | 1/20 | 98 |
16 | 160 | 1/10 | 98 |
16 | 80 | 1/5 | 90 |
8 | 1280 | 1/160 | 80 |
8 | 640 | 1/80 | 70 |
8 | 320 | 1/40 | 85 |
8 | 160 | 1/20 | 85 |
8 | 80 | 1/10 | 70 |
8 | 40 | 1/5 | 50 |
对照水 | - | - | 0 |
Claims (13)
1.式(I)的烷氧化胺提高含有杀真菌三唑的杀真菌制剂活性的用途
其中
R1为C8-20烷基;
R2为-[CH2CH(X)O]bH (a-1)或
n为1至4的整数;
每个a,b和c各自独立地为1至20的整数;
每个X各自独立地选自由氢、甲基、乙基、和苯基组成的基团。
2.根据权利要求1的用途,其中R2为式(a-1)的基团。
3.根据权利要求1的用途,其中R2为式(a-2)的基团。
4.根据权利要求1的用途,其中式(I)的烷氧化胺是N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷。
5.根据权利要求1至4的用途,其中杀真菌三唑选自戊环唑、糠菌唑、环唑醇、噁醚唑、氧唑菌、腈苯唑、喹唑菌酮、氟硅唑、己唑醇、ketoconazole、环戊唑菌、戊菌唑、丙环唑、戊唑醇、氟醚唑、和戊叉唑醇。
6.根据权利要求5的用途,其中杀真菌三唑是丙环唑。
7.一种杀真菌组合物,其中包含一或多种选自下述的杀真菌三唑:戊环唑、糠菌唑、环唑醇、噁醚唑、氧唑菌、腈苯唑、喹唑菌酮、氟硅唑、己唑醇、ketoconazole、环戊唑菌、戊菌唑、丙环唑、戊唑醇、氟醚唑、和戊叉唑醇,加上权利要求1定义的式(I)的烷氧化胺;和载体。
8.根据权利要求7的组合物,其中杀真菌三唑是丙环唑。
9.根据权利要求7的组合物,其中杀真菌三唑是环唑醇和丙环唑的混合物。
10.根据权利要求7至9任一的组合物,其中式(I)的烷氧化胺是N,N’,N’-三(2-羟乙基)-N-椰子烷基-1,3-二氨基-丙烷。
11.根据权利要求7至10任一的组合物,其中杀真菌三唑与式(I)的烷氧化胺的比例范围为5∶1至1∶200,优选2∶1至1∶20。
12.权利要求7至11任一要求保护的组合物的制备方法,其特征在于一或多种杀真菌三唑和式(I)的烷氧化胺直接与载体混合。
13.保护木材、木制品或可生物降解材料的方法,其中包含将权利要求7至11任一要求保护的组合物使用到木材、木制品或可生物降解材料。
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CZ305339B6 (cs) * | 2014-05-23 | 2015-08-05 | ÄŚeskĂ© vysokĂ© uÄŤenĂ technickĂ© v Praze, Fakulta stavebnĂ | Výrobek na bázi dřeva odolný vůči dřevozbarvujícím houbám a plísním |
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JPS6051102A (ja) * | 1983-08-31 | 1985-03-22 | Hokko Chem Ind Co Ltd | 安定化された農園芸用殺菌剤 |
JPS61151102A (ja) * | 1984-12-26 | 1986-07-09 | Hokko Chem Ind Co Ltd | 安定化された農園芸用殺菌剤 |
GB8908794D0 (en) | 1989-04-19 | 1989-06-07 | Janssen Pharmaceutica Nv | Synergistic compositions containing propiconazole and tebuconazole |
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EP1273233A1 (en) * | 2002-07-03 | 2003-01-08 | Janssen Pharmaceutica N.V. | Preservative formulations comprising an oxathiazine and alkoxylated amines |
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- 2003-02-03 AT AT03704526T patent/ATE324041T1/de active
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN114190392A (zh) * | 2021-12-29 | 2022-03-18 | 河北中保绿农作物科技有限公司 | 一种包含苯醚甲环唑和酮康唑的杀菌组合物及其应用 |
CN114190392B (zh) * | 2021-12-29 | 2023-03-10 | 河北中保绿农作物科技有限公司 | 一种包含苯醚甲环唑和酮康唑的杀菌组合物及其应用 |
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US8338338B2 (en) | 2012-12-25 |
ES2262973T3 (es) | 2006-12-01 |
JP2005516981A (ja) | 2005-06-09 |
RU2004126697A (ru) | 2006-01-27 |
BR0307334A (pt) | 2004-12-07 |
AU2003206827A1 (en) | 2003-09-02 |
EP1473996A1 (en) | 2004-11-10 |
RU2312498C2 (ru) | 2007-12-20 |
MY130685A (en) | 2007-07-31 |
CA2474004A1 (en) | 2003-08-14 |
US7662748B2 (en) | 2010-02-16 |
US20050080089A1 (en) | 2005-04-14 |
DK1473996T3 (da) | 2006-08-21 |
DE60304832D1 (de) | 2006-06-01 |
HK1079401A1 (en) | 2006-04-07 |
US20100099724A1 (en) | 2010-04-22 |
EP1473996B1 (en) | 2006-04-26 |
DE60304832T2 (de) | 2006-12-28 |
NO20043700L (no) | 2004-09-02 |
JP4848119B2 (ja) | 2011-12-28 |
CN100399897C (zh) | 2008-07-09 |
PT1473996E (pt) | 2006-09-29 |
AU2003206827B2 (en) | 2007-08-16 |
IL163325A (en) | 2010-11-30 |
PL370299A1 (en) | 2005-05-16 |
CA2474004C (en) | 2011-02-01 |
NZ534780A (en) | 2005-04-29 |
PL206765B1 (pl) | 2010-09-30 |
SI1473996T1 (sl) | 2006-10-31 |
WO2003065807A1 (en) | 2003-08-14 |
ATE324041T1 (de) | 2006-05-15 |
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