CN100369905C - 抗菌防污的噻嗪及其氧化物 - Google Patents
抗菌防污的噻嗪及其氧化物 Download PDFInfo
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- CN100369905C CN100369905C CNB001352369A CN00135236A CN100369905C CN 100369905 C CN100369905 C CN 100369905C CN B001352369 A CNB001352369 A CN B001352369A CN 00135236 A CN00135236 A CN 00135236A CN 100369905 C CN100369905 C CN 100369905C
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- Prior art keywords
- alkyl
- monomer
- phenyl
- compound
- agent
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- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
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Abstract
使用通式(I)的3-芳基-5,6-二氢-1,4,2-噻嗪及其氧化物作为抗菌剂、抗酵母剂、抗真菌剂、杀藻剂、抗甲壳动物剂、杀软体动物剂和通用防污剂以及含有相同物质的组合物,式中n是0、1或2;R1是氢、C1-4烷基或苄基;R代表(a)苯基;取代的苯基;萘基;吡啶基;噻吩基;呋喃基;或者取代的噻吩基或呋喃基;或R代表如下通式的基团,式中X是氧或硫;Y是氮,CH或C(C1-4烷氧基);且R″是氢或C1-4烷基。
Description
本发明涉及一种用3-芳基-5,6-二氢-1,4,2-噻嗪及其氧化物控制细菌和污垢生物的方法,一种保护非木非生物材料的方法,和工业抗菌防污组合物,暴露于潮湿环境或水环境的物体表面容易附生微生物,偶尔也附生其它更高级的生命形式,如软体动物和甲壳动物。当这些生物定居或附着到所述表面上时,暴露物体的价值便随之下降。该物体的外表面,但可能也包括其内表面,可能会恶化,表面状况改变(例如,从光滑、清洁和流线型变成粗糙、污垢和湍流型),物体重量因生物及其遗留物的沉积而增加,该物体周围也可能变得阻塞或拖累。有关物体和系统的功能下降,水环境的质量恶化。类似的问题侵袭着工业上使用的组合物如涂料、润滑剂等。所有这些现象统称污垢。本方法的噻嗪及其氧化物在US-4,569,690中是作为除草剂、植物杀真菌剂、植物干燥剂和脱叶剂公开的。
本发明提供一种控制细菌和污垢生物的方法,所述方法包括向所述细菌或污垢生物或向其所在部位施用一有效抗菌或防污量的如下通式化合物,
式中n是0、1或2;R1是氢、C1-4烷基或苄基;且R代表(a)苯基;被1~3个独立选自下列的取代基团取代的苯基:羟基,卤原子,C1-12烷基、C5-6环烷基、三卤甲基,苯基,C1-5烷氧基,C1-5烷硫基,四氢吡喃氧基,苯氧基,C1-4烷羰基,苯甲酰,C1-4烷基亚磺酰,C1-4烷基磺酰,羧基或其碱金属盐,C1-4烷氧羰基,C1-4烷氨基羰基,苯氨基羰基,甲苯氨基羰基,吗啉代羰基,氨基,硝基,氰基,二氧戊环基或C1-4烷氧亚氨基甲基;萘基;吡啶基;噻吩基,较好当n不是2时;呋喃基;或者被1~3个独立选自下列的取代基团取代的噻吩基或呋喃基:C1-4烷基,C1-4烷氧基,C1-4烷硫基,卤原子,氰基,甲酰,乙酰,苯甲酰,硝基,C1-4烷氧羰基,苯基,苯氨基羰基和C1-4烷氧亚氨基甲基;或R代表如下通式的基团,
式中X是氧或硫;Y是氨,CH或C(C1-4烷氧基);且R″是氢或C1-4烷基。
具体地说,本发明提供一种保护非木非生物材料以及由所述非生物材料构成或覆盖了所述非生物材料的物体不受细菌和/或污垢生物损害的方法,所述方法包括向该表面施用或向所述材料或物体中掺入一有效抗菌或防污量的通式(I)化合物。
在上述定义中,卤原子系指氟、氯、溴和碘;C1-4烷基系指有1~4个碳原子的直链或支链饱和烃基,包括甲基、乙基、正丙基、1-甲基乙基、正丁基、1,1-二甲基乙基、1-甲基丙基、2-甲基丙基;C1-5烷基包括以上所定义的C1-4烷基基团,和有5个碳原子的饱和烃基,如正戊基和支化的戊基异构体;C1-5烷基包括以上定义的C1-5烷基,和含6个碳的同系物,如正己基和支化的己基异构体。C1-12烷基包括C1-5烷基,和有7~12个碳原子的饱和烃基,如庚基、辛基、壬基、癸基、十一烷基、十二烷基及其异构体。碱金属阳离子这一术语具体地指钠或钾阳离子。三卤甲基系指一个有卤原子充分取代的甲基基团,具体地指三氟甲基和三氯甲基。C1-4烷氧亚氨基甲基系指通式-CH=N-O-C1-4烷基的基团。
本方法中使用的通式(I)的具体化合物是这样的化合物,其中n是0、1或2;R1是氢、C1-4烷基或苄基;且R代表苯基;萘基;吡啶基;若n不是2,则为噻吩基;呋喃基,它任选地带有1~3个独立地选自C1-4烷基和C2-5烷氧羰基的取代基;或带有1或2个取代基的苯基,该取代基独立地选自羟基、卤素、C1-12烷基、C5-6环烷基、三卤甲基、苯基、C1-5烷氧基、C1-5烷硫基、四氢吡喃氧基、苯氧基、C2-5烷羰基、苯甲酰、C1-4烷基亚磺酰、C1-4烷基磺酰、羧基或其碱金属盐、C1-5烷氧羰基、C2-5烷氨基羰基、苯氨基羰基、甲苯氨基羰基、吗啉代羰基、氨基、硝基、氰基或二氧戊环基。
有价值的是这样的化合物,其中n是1,且R代表苯基、噻吩基或带有1或2个选自卤素和三卤甲基等取代基的苯基;或这样的化合物,其中n是2,且R代表苯基,或带有1或2个选自卤素和三卤甲基的取代基的苯基。
更有价值的是这样的化合物,其中R1是氢,n是1或2,且R代表苯基、C1-6烷基苯基、卤苯基、二卤苯基、联苯基、C1-5烷氧苯基、三卤甲基苯基、硝基苯基、被C2-5烷氧羰基取代的苯基、C1-5烷基硝基苯基、无取代基的呋喃基或噻吩基,或者有乙氧羰基、氰基、氯或溴取代的呋喃基或噻吩基。
特别有价值的是这样的化合物,其中R1是氢,n是1或2,且R代表3-氟苯基、4-氯苯基、3,4-二氯苯基、3,5-二氯苯基、3-三氟甲基苯基、4-三氟甲基苯基、4-甲基苯基、3-乙酰苯基、3-硝基苯基、3-甲基-4-硝基苯基或2-噻吩基。
也更为有价值的是通式(I)的这样一些化合物,其中R1是氢,R是通式(b)的基团,式中X是硫、Y是氮或CH且R″是氢。
较好的化合物是5,6-二氢-3-(2-噻吩基)-1,4,2-噻嗪,4-氧化物和3-(4-氯苯基)-5,6-二氢-1,4,2-噻嗪,4,4-二氧化物。
通式(I)的所有化合物均可遵循US-4,569,690中所述的步骤进行制备。
通式(I)化合物有抗革兰阳性菌的活性,更重要的是用于材料保护,也有抗革兰阴性菌的活性。敏感菌有下列各属,例如,气单孢菌属,产碱杆菌属,短杆菌属,纤维单孢菌属,柠檬酸细菌属,棒状杆菌属,肠杆菌属,埃希氏杆菌属,克雷伯氏菌属,微球菌属,变形杆菌属,普罗威登斯菌属(Providencia)、假单孢菌属,Shewanella,Acinobacter,杆菌属,沙雷氏菌属,葡萄球菌属,链球菌属和黄单孢菌属。
通式(I)化合物还有抗污垢生物的活性。“污垢生物”(foulingorganisms)这一术语系指能生长在或粘着到各种表面上的生物,尤其是在潮湿环境或水环境中,例如海洋水体、淡水体、微咸水体、雨水,以及冷却水、排水、废水和下水。污垢生物是藻类,例如,微型藻,如双眉藻属、曲壳藻属、舟形藻属、茧形藻属、直链藻属、卵形藻属、衣藻属、小球藻属、丝藻属、鱼腥藻属、褐指藻属、紫球藻属;大型藻,如浒苔属、刚毛藻属、水云属、顶丝属、仙菜属、多管藻属;软体动物,如贻贝属;甲壳动物,如卤虫属、藤壶属、扁藤壶属、Modestus、花笼属、茗荷属;及海鞘,水螅水母类和苔藓虫类。
本发明也提供一种使非木非生物材料能抵御那些会使此类材料腐败或破坏的真菌作用的防腐方法。所述方法涉及用一有效杀真菌量的通式(I)化合物处理这样的材料。
通式(I)化合物可用来保护种类繁多的非木非生物材料,以及由其构成或被其覆盖的物品。非生物材料和由其构成或被其覆盖的物品的实例包括粘合剂;胶料;纸和纸板;纸浆;纺织品;皮革;油漆;塑料,如聚氯乙烯(PVC)和聚酯;工业组合物,例如冷却介质如冷却润滑剂和切削液,涂料组合物,浴液组合物(工艺液体),润滑剂等;金属与合金,例如铁材和钢材;建筑材料,如砖、(铺地面)石材、水泥和混凝土;装修材料,如石膏、瓦;以及可能被细菌、真菌或污垢生物沾污或破坏的任何其它材料。
特别重要的是通常用于装修和保护目的涂布材料。本发明方法尤其适用于保护粘合性涂料,不管是透明的还是着色的(即包含一种或多种染料或颜料),也不管是天然的还是合成的,例如油漆-尤其防污油漆组合物、清漆、大漆、末道漆、白涂料和类似涂料。本发明保护所述涂布材料的方法的特别适宜性寓于如下事实:该方法中采用的噻嗪不仅有效地保护贮存容器中的涂布材料,即“罐内”保护(尤其防止细菌作用),从而确保长久的适用(或罐装)期和良好的贮存稳定性,而且当该涂布材料已在基质上涂布成薄膜时也能有效地保护该涂布材料和任选地保护其下面的所述基质(“薄膜”保护)。这些噻嗪兼备对涂料的“罐内”和“薄膜”双重保护的效用具有很大的实用价值。
作为由所述非生物材料构成或覆盖的构筑物,可以提到的有游泳池、浴缸、冷却水循环回路和各种装置如制造装置或空调装置中的工业浴槽,其功能会因细菌和污垢生物的存在和/或繁衍而受损害。进一步实例是建筑物和建筑物组成部分,例如经常受潮气侵蚀的地方如地窖、浴室、橱房、洗衣房等的地板、内外墙或天花板,以及细菌和/或污垢生物的温床。这些生物的存在不仅从卫生学和美学的观点来看是有问题的,而且也会造成经济损失,因为所述建筑物和/或装修材料的恶化比预期的还要快。
本发明方法尤其适用于保护水下物品,例如,船体、港口设施、干船坞、过水闸门、过船闸、系泊柱、浮标、钻井平台、桥梁、管道、鱼网、缆绳和总是或经常与水接触的任何其它物品,其办法是给所述物品涂布一种包含有效防污量的通式(I)化合物的防污组合物,如油漆组合物。
在这一方面,应当注意的是,本发明方法提供一种比目前使用基于氧化亚铜等重金属的防污产品或基于有机锡化合物等有机金属衍生物的防污产品的方法更安全和生态上更可接受的替代。这些噻嗪对哺乳动物的毒性是可接受的,因而它们对人体的危险性较小,无论这些化合物通过直接物理接触(例如在处置或施用期间)还是通过食物链到达人体都是如此。它们的生物可降解性确保它们在环境中的存留时间不太长,也确保它们引起较小和较短的环境污染与压力。这些噻嗪的化学稳定性还意味着它们能与大多数这样的非生物材料兼容,而且确实需要特殊预防措施,例如添加能使该活性组分稳定的药剂。在应形成薄膜的材料如润滑剂、切削液和涂布材料中,它们不损害均匀薄膜的形成和实用性。具体地说,在涂布材料中,它们不影响实用环境如室温和室外条件下的快速固化,并使该组合物能强有力地粘合到基质和/或面漆上。
施用方法是按照预期目的和盛行环境条件进行选择的。例如,在保护润滑剂、涂料或切削液的情况下使用的技术包括:该活性组分可以在制造工艺期间混入所述润滑剂、涂料或切削液中,也可以在此后混入成品中。活性组分可以以纯粹形式添加,也可以溶解或分散在足够量的稀释剂中。较好的是,该稀释剂由一种或多种要在最终组合物中存在的溶剂组成。
本发明方法也包括通式(I)化合物,任选地以一种适当配方,用技术上已知的任何一种技术,例如刷涂、喷涂、雾化、滴涂、浸溃、浸没、散射和注入,施用到非生物材料上。在一些情况下,施用可以包括使用压力或真空系统、热系统、注射或扩散的浸溃技术。
适当的配方是按照技术上已知的步骤配制成可乳化的浓制剂、可直接喷雾或稀释的溶液、可湿性粉剂、可溶性粉剂、膏剂、尘剂、涂料组合物,例如油漆,尤其防污油漆组合物,清漆等。例如,该活性化合物可以与一种由液体、半固体或固体载体组成的增充剂和任选地表面活性剂如乳化剂和/或分散剂混合。在涂料组合物中,该活性化合物可以有利地并入聚合物、共聚物或树脂中。这些可以由如下单体组成:二烷基(二甲基)硅氧烷,(甲基)丙烯酸,(甲基)丙烯酸酯,乙烯醇和烯丙醇以及衍生的酯(如乙酸乙烯酯),马来酸,苯乙烯,氯乙烯,丁二烯,丙烯酰胺,丙烯腈和类似可共聚单体。作为树脂,可以提到的有醇酸树脂、聚氨酯、环氧树脂、酚醛树脂和脲醛树脂。所述组合物中进一步有用的添加剂包括抗水剂和表面滑动剂,这些能赋与该涂料组合物的聚合物或共聚物所形成的涂层薄膜以低表面张力。
在本发明组合物中可以使用任何一种既不干扰活性组分的抗菌活性也不干扰其防污活性的适用载体或添加剂。用于诸如尘剂和粉剂的固体载体或填料包括有机性能或无机性质的各种惰性、多孔和粉状分配剂,例如,天然矿物填料,如方解石、滑石、高岭土、蒙脱石或美国活性白土,或有机性质的填料,如粉末状软木、锯末及其它微细粉状材料。为了改善其物理性能,可能有利的是添加高度分散的硅酸或高度分散的吸收剂聚合物。适用的颗粒状吸收剂载体是多孔类型的,例如,浮石、碎砖、海泡石或膨润土;而适用的非吸收剂载体是方解石或砂子等材料。该活性组分与这些载体物质是诸如通过一起研磨混合的;此外,也可以让惰性载体物质浸溃该活性成分在一种易挥发溶剂中的溶液,然后通过加热或减压抽吸过滤除去溶剂。通过添加润湿剂和/或分散剂,也能容易地使这样的粉状制剂成为可用水湿润的,从而在稀释时得到悬浮液。
用于生产液体制剂的惰性稀释剂较好应当不是容易可燃的,且应尽可能对有关环境中的非靶动物或植物和人体是无毒的。适用于这一目的的稀释剂是诸如水或有机溶剂,例如,芳烃,如甲苯、二甲苯混合物、有取代的萘;醇和二醇及其醚和酯,如乙醇、乙二醇、乙二醇单甲醚或单乙醚;酮,如2-丙酮、环己酮等;强极性溶剂,如N-甲基-2-吡咯烷酮、二甲基亚砜或二甲基甲酰胺;植物油或环氧化植物油,如环氧化的椰子油或豆油,及其混合物。溶液可以用常用方式制备,如有必要可借助于溶解促进剂。可以使用的其它液体形式包括该活性化合物在水或适用惰性稀释剂中的乳液、分散液或悬浮液,也可以包括用于制备这样的乳液、分散液或悬浮液、可直接调制成所需浓度的浓制剂。为此目的,使该活性组分诸如与一种分散剂、悬浮剂或乳化剂混合。也可以使该活性成分溶解或分散于一种适用惰性溶剂中,且同时或随后与一种分散剂或乳化剂混合。也可以使用霜剂、软膏剂、糊剂或蜡状性质的半固体载体物质,可向其中掺入该活性组分,如有必要,还可借助于溶解促进剂和/或乳化剂。凡士林、石油蜡、液体石蜡、硅油及其它霜剂基料是半固体载体物质的实例。该活性组分也有可能以气溶胶形式使用。为此目的,使该活性组分溶解或分散于一种适合于作为推进剂使用的挥发性液体,例如,甲烷和乙烷的氯代和/或氟代衍生物及其混合物中,或压缩空气中。这样,便得到了加压溶液,这种溶液在喷雾时产生气溶胶,特别适用于控制或杀灭诸如密闭空间和贮藏室中的细菌和/或污垢生物。为了后一个目的,也可以使用含有该活性组分的烟雾发生器。
除通式(I)化合物和载体外,适用配方还经常包含配制技术上常用的其它助剂。这些助剂取决于具体用途和用户的偏爱。这样的助剂是,例如,有机活化剂(如能形成化学干燥有机粘合剂的聚合物,如醇酸树脂,或能通过溶剂蒸发形成物理干燥有机粘合剂);杀虫剂,例如,氯代烃如硫丹,有机磷酸酯如毒死蜱,合成除虫菊酯类如氯菊酯等;附加的杀真菌剂和杀菌剂,例如,醇类如乙醇、2,3,3-三碘烯丙醇、醛类如甲醛、戊二醛;释放甲醛的化合物,如2-溴-2-硝基丙-1,3-二醇(溴硝丙二醇),2-溴-2-硝基丙-1-醇;胺和甲醛的反应产物,如三嗪、3,5-二甲基-四氢-1,3,5-2H-噻二嗪-2-硫酮;酰胺和甲醛的反应产物,如1-羟甲基-2-硫羰-1:2-二氢苯并噻唑基-N-羟甲基苯并噻唑啉硫酮;苯酚类,如2-苯基苯酚,五氯苯酚;有机酸类,如丙酸、苯甲酸、水杨酸、环烷酸铜盐;无机酸类,如硼酸;酰胺类,如2,5-二甲基-N-环己基-N-甲氧基呋喃-3-甲酰胺;氨基甲酸酯,如N-丁基氨基甲酸3-碘炔丙酯(IPBC),N-苯并咪唑-2-基氨基甲酸甲酯(多菌灵),N-(1-丁基氨基甲酰)苯并咪唑-2-基氨基甲酸甲酯(苯菌灵),二甲基二硫代氨基甲酸锌,亚乙基二硫代氨基甲酸锌,二(二甲基二硫代氨基甲酰)二硫;吡啶衍生物,如2-巯基吡啶-N-氧化物,2-氯-6-(三氯甲基)吡啶,2,3,5,6-四氯-4-(甲基磺酰)吡啶,8-羟基喹啉铜,1-乙基-1,4-二氢-7-甲基-4-氧代-1,8-二氮杂萘-3-羧酸;吡咯类,如戊唑醇,丙环唑,戊环唑,烯菌灵;杂环化合物,如2-甲基-2(2H)-异噻唑酮,5-氯-2-甲基-3(2H)-异噻唑酮,,2-正辛基-4-异噻唑啉-3-酮,4,5-二氯-2-(正辛基)-4-异噻唑啉-3-酮,1,2-苯并异噻唑啉-3-酮,2-甲基-4,5-亚丙基-4-异噻唑啉-3-酮,2-(4-噻唑基)苯并咪唑,2-巯基苯并噻唑,2-(硫氰基甲硫基)苯并噻唑;N-卤烷硫基化合物,如N-三氯甲硫基硫代邻苯二甲酰亚胺,灭菌丹,N-三氯甲硫基-4-环己烷-1,2-二甲酰亚胺,克菌丹,N-1,1,2,2-四氯乙硫基-4-环己烯-1,2-二甲酰亚胺,敌菌丹,抑菌录,对甲抑菌录;有活化卤素基团的化合物,如百菌清;表面活性剂,如胍类和双胍类;有机金属化合物,如二(三正丁基锡)氧化物,三丁基锡酯,环烷酸三丁基锡,亚油酸三丁基锡,苯甲酸三丁基锡,氟化三丁基锡;各种化合物,如匹马菌素,克啉菌,双硫氰酸亚甲酯,甲苯基砜,二氰基丁烷;金属盐,如铬铜砷;活性天然产品,如链霉素;辅助溶剂,如乙酸乙基乙二醇酯和乙酸甲氧基丙酯;加工添加剂;固定剂,如羧甲基纤维素,聚乙烯醇,石蜡;增塑剂,如苯甲酸酯,和邻苯二甲酸酯,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯、邻苯二甲酸二月桂酯;紫外线稳定剂或稳定性增强剂;染料;着色颜料;催干剂,如辛酸钴、辛酸铅和环烷酸钴;腐蚀抑制剂;抗沉降剂;防结皮剂,如甲基乙基酮肟;消泡剂等。一般来说,这些助剂不是本发明的实施所必需的,但纳入具体配方中,尤其包括在涂料配方中,以优化总有效性和便于施用。它们可以以常用数量用于本发明。
以本发明方法采用的抗菌和/或防污组合物,以组合物总重量为基准按重量计,可以含0.001~95%活性组分。可直接使用的组合物如油漆较好含有0.5~20%、尤其1~10%(重量)活性组分。另一方面,防污油漆组合物,以所述组合物干质量的总重量为基准按重量计,可以含10~75%、尤其20~70%通式(I)活性组分(即以该防污组合物的总重量为基准按重量计,可含多达50%、尤其5~25%活性组分)。较好的组合物尤其包含下列成分(所有百分率均以重量计):
可乳化浓制剂:
活性组分: 1~20%,较好5~10%
表面活性剂: 5~30%,较好1 0~20%
液体载体: 50~94%,较好70~85%
粉剂:
活性组分: 0.1~10%,较好0.1~1%
固体载体: 99.9~90%,较好99.9~90%
悬浮液浓制剂
活性组分: 5~75%,较好1 0~50%
水: 94~25%,较好88~30%
表面活性剂: 1~40%,较好2~30%
颗粒剂
活性组分: 0.5~30%,较好3~15%
固体载体: 99.5~70%,较好97~85%
以下实例无意限制而只是说明本发明的范围。
A.生物学实例
实例1:对细菌和酵母菌的抗菌功效
试验溶液的制备是把表1-4中的化合物溶解在50%乙醇中,再进一步用无菌蒸馏水稀释。这些试验溶液用移液管移至佩特里细菌培养皿,并与温胰蛋白琼脂混合,达到活性组分浓度为100ppm。冷却后,该培养基与下列酵母或细菌一起培养:
汉逊德巴利酵母(酵母菌) (A)
产碱假单孢菌(革兰阴性菌) (B)
仙影拳真菌状杆菌(革兰阳性菌) (C)
铜绿色假单孢菌(革兰阴性菌) (D)
黄杆菌属(未定名种)(革兰阴性菌) (E)
白链霉菌(革兰阳性菌) (F)
产气肠杆菌(革兰阴性菌) (G)
大肠埃希氏杆菌(革兰阴性菌) (H)
在未处理培养物充分生长后,用下列评分体系评估这些化合物:
0=生长速度与对照组相等
1=生长受到该化合物抑制
2=在该化合物影响下无生长
对本发明化合物的抗菌与防污功效评定的分数列于表1~4中。
“-”号表示该化合物未进行测试。
表1
化合物 | 细菌 | |||||||||
化合物号 | n | R | A | B | C | D | E | F | G | H |
123 | 121 | 4-氯苯基2,4-二氯苯基3-硝基苯基 | 222 | 102 | 222 | 001 | 222 | 202 | 001 | 202 |
化合物 | 细菌 | |||||||||
45678910111213141516171819202122232425262728 | 1211111221112222111221121 | 3,4-二氯苯基甲基苯基3-氟苯基2-呋喃基2-噻吩基3-甲氧基苯基4-甲基苯基4-甲基苯基2-呋喃基3-三氟甲基苯基4-乙酰苯基2,6-二氯苯基2,6-二氯苯基苯基4-氯苯基3,5-二氯苯基4-丁氧基苯基3,5-二氯苯基4-苯甲酸乙酯3-氯苯基4-三氟甲基苯基4-三氟甲基苯基3-苯甲酸甲酯3-溴苯基4-乙氧基苯基 | 22222022022120--0--0----- | 1011201100100010021001010 | 2222202102212022020022220 | 0000101100100000000000000 | 2222202202200022022022222 | 2220202102200022022022222 | 0000200000000000000020000 | 2120202002200000000000020 |
表2
化合物号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | X | n | M.P.(℃) |
2930313233343536373839404142434445464748495051525354555657 | HHHHHHHHHHHHHHHHHHHHHCH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>HHHHH | HHHCH<sub>3</sub>CH<sub>3</sub>HHHCH<sub>3</sub>HHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHCO<sub>2</sub>CH<sub>3</sub>BrBrBrCO<sub>2</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>HHHHHHHHHHH | CO<sub>2</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>3</sub>HHHBrBrHBrCH<sub>3</sub>HHHCH<sub>3</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>HHHCO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>CNCN | OOOSSSSSSSOSSSOOSSSSSSSSSSSSS | 02101201220012211201212001201 | 85-89126-129118-119oil73-7599-10182-83113-11460-62118-11987-8874-75169-173126-127156-157147-148150-152125-12662-63109-111101-102114-115147-14870-7268-69109-110123-124136-137160-162 |
化合物号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | X | n | M.P.(℃) |
5859606162636465666768697071727374757677 | HHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHNO<sub>2</sub>CH<sub>3</sub>CH<sub>3</sub>BrCOOHCONHC<sub>6</sub>H<sub>5</sub>CONHC<sub>6</sub>H<sub>5</sub>CONHC<sub>6</sub>H<sub>5</sub> | CNClClClCHONO<sub>2</sub>NO<sub>2</sub>NO<sub>2</sub>CH=NOCH<sub>3</sub>C<sub>6</sub>H<sub>5</sub>C<sub>6</sub>H<sub>5</sub>C<sub>6</sub>H<sub>5</sub>C<sub>6</sub>H<sub>5</sub>BrBrCH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub>CH<sub>3</sub> | SSSSSSSSSSSSSSSSOOOO | 20120012201200100000 | 153-15574-77102113-11448-49162-163186-188160-161168-170100-103144-14795-98140-145oil100-10464-67 |
表2a
化合物号 | R<sup>2</sup> | n | M.P.(℃) |
7879 | HH | 21 | 102-104106-107 |
表3
化合物号 | R” | X | Y | n | M.P.(℃) |
808182838485868788899091 | HHHHHHHHHCH<sub>3</sub>CH<sub>3</sub>H | OOOSSSSSSOOS | NNNNNNCHCHCHNNC-OCH(CH<sub>3</sub>)<sub>2</sub> | 210201012121 | 255190-191143-144226-227150-151192-195132-134140-142150-154209-210215-216oil |
表4
化合物号 | R<sup>8</sup> | R<sup>9</sup> | R<sup>10</sup> | n | M.P.(℃) |
9293949596979899100 | HHFFFCF<sub>3</sub>CF<sub>3</sub>CF<sub>3</sub>F | FFFFFHHHH | HHHHHCF<sub>3</sub>CF<sub>3</sub>CF<sub>3</sub>F | 212101020 | 136-138132-133106-108128-13063-65110-11344-4876-78103-104 |
化合物号 | R<sup>8</sup> | R<sup>9</sup> | R<sup>10</sup> | n | M.P.(℃) |
101102103104105106107 | FFCO<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>CO<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>CO<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>HH | HHClClClCH=NOCH<sub>3</sub>CH=NOCH<sub>3</sub> | FFHHHHH | 2101212 | 108-110138-139oil127-12982-8385-87104-106 |
实例2:抗淡水藻类的功效
9ml合适当浓度试验化合物的Bold藻类液体培养基在一个5.5cm直径塑料佩特里培养皿中,与1ml三种绿藻(臭气衣藻(Chlamydcmonas dysosmos)、小球藻(Chlorella vulgaris)或环丝状丝藻(Ulothrix confervicola))之一或蓝绿藻(柱状鱼腥藻(Anabaena cylindrica))的两周龄原种培养液一起温育。这些培养皿放在一间气候室中,在光合作用活性辐射水平为40μmole·m-2·sec-1之下,在昼间(16h)20℃和夜间(8h)18℃培养。14天后进行评估,用目测法估计与对照组相比的藻类生长百分率。结果表示为给出90%死亡率的最低试验浓度(ppm)。
化合物 | 浓度(ppm) | |||||
化合物号 | n | R | 臭气衣藻 | 小球藻 | 丝环状丝藻 | 柱状鱼腥藻 |
4818192125 | 112211 | 3,4-二氯苯基2-噻吩基4-氯苯基3,5-二氯苯基3,5-二氯苯基4-三氟甲基苯基 | 2.52.52.5512.5 | 1051010510 | 2.5152.512.5 | 2.52.52.52.52.55 |
实例3:抗海洋藻类的功效
9ml含适当浓度试验化合物的Provasoli ASP-2(人工海水-2)培养基在一个5.5cm直径塑料佩特里培养皿中,与1ml硅藻(三角褐指藻(Phaeodactylum tricornutum))或单细胞赤藻(紫球藻(Porphyridium sp.))的两周龄原种培养液一起温育。这些培养皿放在一间气候室中,在光合作用活性辐射水平为40μmole·m-2·sec-1之下,在昼间(16h)20℃和夜间(8h)18℃培养。14天后进行评估,用目测估计与对照组相比的藻类生长百分率。化合物1、2、3、4、5、14、15、16、18、19、21、25、27在等于或低于1ppm的浓度水平引起90%死亡率。
实例4:抗卤虫属(Artemia)的功效
向1ml含不同数量试验化合物的人工海水中添加15条卤虫属二龄期幼虫。在连续照明静态培养24小时后,评估该试验。化合物2、4、5、11、13、18、19在等于或低于10ppm的浓度水平引起100%死亡率。
B.组合物实例(所有百分率均按重量计)
实例5:通式(I)固体化合物组合物实例
a)可乳化浓制剂:这些浓制剂用于稀释可以得到任何浓度的乳液。
a) b)
通式(I)化合物 10% 1%
辛基苯酚聚甘醇醚(4~5摩尔环氧乙烷) 3% 3%
十二烷基苯磺酸钙 3% 3%
蓖麻油聚甘醇醚(36摩尔环氧乙烷) 4% 4%
环己酮 30% 10%
二甲苯混合物 50% 79%
b)粉剂:是通过使活性组分与载体混合,并在一台适用磨机中研磨该混合物得到的。
a) b)
通式(I)化合物 0.1% 1%
滑石粉 99.9% -
高岭土 - 99%
c)悬浮液浓制剂,这些浓制剂用水稀释可以得到任何预期浓度的悬浮液,其制备是使精细研磨的活性组分与助剂充分混合。
a) b)
通式(I)化合物 40% 5%
乙二醇 10% 10%
壬基苯酚聚甘醇醚(1 5摩尔环氧乙烷) 6% 1%
木质素硫酸钠 10% 5%
羧甲基纤维素 1% 1%
37%甲醛水溶液 0.2% 0.2%
硅油,75%水乳液形式 0.8% 0.8%
水 32% 77%
实例6:通式(I)液体活性组分组合物实例
a)可乳化浓制剂:这些浓制剂可用水稀释可以得到任何浓度的乳液。
a) b) c)
通式(I)化合物 20% 40% 50%
十二烷基苯磺酸钙 5% 8% 5.8%
蓖麻油聚甘醇醚(36摩尔环氧乙烷) 5% - -
三丁基苯酚聚甘油醇醚(30摩尔环氧乙烷) - 12% 4.2%
环己酮 - 15% 20%
二甲苯混合物 70% 25% 20%
b)适于以微滴形式施用的溶液剂
a) b) c) d)
通式(I)化合物 80% 10% 5% 95%
乙二醇单乙醚 20% - - -
聚甘醇(MG 400) - 70% - -
N-甲基-2-吡咯烷酮 - 20% - -
环氧化椰子油 - - 1% 5%
石油馏出物
(沸点范围160~190℃) - - 94% -
c)颗粒剂:其制备是把活性组分溶解在二氯甲烷中,把溶液喷洒在载体上,随后使溶剂蒸发。
a) b)
通式(I)化合物 5% 10%
高岭土 94% -
高度分散的硅酸 1% -
美国白土 - 90%
d)粉剂:是通过使载体与活性组分充分混合得到的。
a) b)
通式(I)化合物 2% 5%
高度分散的硅酸 1% 5%
滑石粉 97% -
高岭土 - 90%
实例7:油漆组合物实例
a)通式(I)化合物 6.0%
二氧化钛 17.1%
白粉(研细的白垩) 9.7%
滑石粉 13.2%
六偏磷酸钠 0.1%
羟乙基纤维素(3%水溶液) 12.5%
助溶剂 1.2%
微量添加剂 0.4%
水 27.7%
乙酸乙烯酯/Versatate共聚物乳液 12.1%
b)通式(I)化合物 1.0%
二氧化钛 26.4%
大豆醇酸树脂 44.0%
石油溶剂 27.5%
辛酸钴(8%) 0.3%
辛酸铅(3 3%) 0.7%
甲基·乙基酮肟 0.1%
Claims (5)
1.用于保护非木非生物材料的防止细菌和/或污垢生物的涂料组合物,其包含:
(A)作为活性组分的通式(I)化合物:
式中n是0、1或2;R1是氢、C1-4烷基或苄基;且R代表
(a)苯基;被1~3个独立选自下列的取代基团取代的苯基:羟基,卤原子,C1-12烷基、C5-6环烷基、三卤甲基,苯基,C1-5烷氧基,C1-5烷硫基,四氢吡喃氧基,苯氧基,C1-4烷羰基,苯甲酰基,C1-4烷基亚磺酰基,C1-4烷基磺酰基,羧基或其碱金属盐,C1-4烷氧羰基,C1-4烷氨基羰基,苯氨基羰基,甲苯氨基羰基,吗啉代羰基,氨基,硝基,氰基,二氧戊环基或C1-4烷氧亚氨基甲基;萘基;吡啶基;噻吩基;呋喃基;或者被1~3个独立地选自下列的取代基团取代的噻吩基或呋喃基:C1-4烷基,C1-4烷氧基,C1-4烷硫基,卤原子,氰基,乙酰,苯甲酰,硝基,C1-4烷氧羰基,苯基和C1-4烷氧亚氨基甲基;或R代表如下通式的基团,
式中X是氧或硫;Y是氮或CH;且R″是氢或C1-4烷基,和
(B)从二烷基硅氧烷单体、(甲基)丙烯酸单体、(甲基)丙烯酸酯单体、乙烯醇和烯丙醇单体、乙烯基酯和烯丙基酯单体、马来酸单体、苯乙烯单体、氯乙烯单体、丁二烯单体、丙烯酰胺单体、丙烯腈单体衍生的聚合物或共聚物,或醇酸树脂、聚氨酯、环氧树脂、酚醛树脂和脲醛树脂。
2.按照权利要求1的涂料组合物,其中在式(I)中当n不是2时R代表噻吩基。
3.按照权利要求1的涂料组合物,进一步包含一种或多种选自下列的添加剂:抗水剂;表面滑动剂;有机粘接剂;杀虫剂;杀真菌剂;杀菌剂;辅助溶剂;加工添加剂;固定剂;增塑剂;紫外线稳定剂或稳定性增强剂;染料;着色颜料;催干剂;腐蚀抑制剂;抗沉降剂;抗结皮剂;和消泡剂。
4.按照权利要求1的涂料组合物,以所述组合物干质量的总重量为基准,包含10~75重量%活性组分。
5.按照权利要求1-4任何一项的涂料组合物,其中通式(I)的活性组分是3-(苯并[b]噻吩-2-基)-5,6-二氢-1,4,2-噻嗪4-氧化物。
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US4569690A (en) * | 1982-09-28 | 1986-02-11 | Uniroyal, Inc. | 3-Aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
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CA1273921A (en) * | 1982-09-28 | 1990-09-11 | Walter G. Brouwer | 3-aryl-5, 6-dihydro-1, 4, 2-oxathiazines and their oxides |
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