CN114656462B - 一类含n杂环芳腙类衍生物及其制备方法和用途 - Google Patents
一类含n杂环芳腙类衍生物及其制备方法和用途 Download PDFInfo
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- CN114656462B CN114656462B CN202210293751.1A CN202210293751A CN114656462B CN 114656462 B CN114656462 B CN 114656462B CN 202210293751 A CN202210293751 A CN 202210293751A CN 114656462 B CN114656462 B CN 114656462B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明提供了一类含N杂环芳腙类衍生物及其制备方法和用途,具体涉及一类衍生物,其化学结构通式见式I:I:
Description
技术领域
本发明的技术方案属于农药领域,具体涉及含N杂环芳腙类化合物及其制备方法和用途。
背景技术
水稻是世界上重要的粮食经济作物。随着人口的增长,对水稻的需求也日益增加。然而,水稻病害不仅影响水稻的生产,对稻米的品质和商业价值还有一定的影响,其中水稻纹枯病,水稻稻瘟病和水稻白叶枯病是主要的三大水稻病害(Khush,G.S.et al.Plant MolBiol.2005,59,1-6;Dean,R.A.et al.Nature.2015,434,980-986.)。在水稻病害防治中,杀菌剂发挥着不可替代的作用。目前传统水稻病害防控的农药较少,而新农药的开发是解决水稻病害,保障水稻增产的关键突破口。新农药的创制是我国农药减量增效的重要保障。随着绿色生态农业的发展,绿色农药的创制成为农药未来发展的趋势与挑战(邵旭升等.世界农药,2020,42(04):16-24.)。
嘧菌腙(Ferimzone)(Z)-2′-甲基苯乙酮4,6-二甲基-2-嘧啶基腙,是由日本武田公司开发的一种高效、低毒杀菌剂,其对稻瘟病、叶褐斑病、茎腐病有特效(Okuno,T.etal.Phytopathology.1989,79,827-832)。嘧菌腙化合物具有高效杀菌的性能,其分子结构中含有腙的骨架结构。腙类化合物已广泛应用于药物分子修饰,天然产物合成等多种领域,值得注意的是,含有苯并噻唑腙类结构的化合物也可能具有诱导植物免疫的活性(Setoa,D.et al.Proc.Natl.Acad.Sci.2021,118.47,e2116570118.)。
植物激活剂作为一种新型的绿色农药在生产和实践中具有很大的应用前景。植物激活剂是指本身或其代谢产物没有直接的杀菌作用,但可以诱导植物产生持久的免疫抗病能力的一类新型杀菌剂(张越等.中国科学基金,2020,34(04):519-528)。苯并噻二唑是最早开发出的商品化小分子植物激活剂,之后又陆续开发出2,6-二氯异烟酸(INA)、噻酰菌胺(TDL)、烯丙异噻唑(PBZ)、氟唑活化酯和甲噻诱胺等。这些植物激活剂均含有独特的N,S杂环的结构。
本发明将具有诱导抗病活性的含N杂环结构单元引入到嘧菌腙的核心骨架中,以期望设计合成兼具有诱导抗病活性的杀菌剂。因此,基于农药分子合理设计及绿色农药创制的角度出发,通过采用生物电子等排替换原理,设计合成了一系列含N杂环的芳基腙类衍生物,并进行了系统的杀菌活性评价。
发明内容
本发明所要解决的技术问题是:提供一类新的含N杂环芳腙类衍生物的合成方法,提供这类化合物调控农业、园艺和卫生以及林业植物害虫和植物病原物的生物活性及其测定方法,同时提供这些化合物在农业领域、园艺领域、林业领域以及卫生领域中的应用。
本发明解决该技术问题所采用的技术方案是:具有农业领域、园艺领域、林业领域杀虫、杀螨活性、杀菌活性、抗植物病毒活性、诱导植物产生抗病活性的含N杂环芳腙类衍生物的化学结构通式如I所示:
其中,Hetro选自:4-甲基1,2,3-噻二唑-5-基、2,6-二氯吡啶-4-基、苯并[d][1,2,3]噻二唑-7-基、3,4-二氯异噻唑-5-基、Ar选自:嘧啶-2-基、4,6-二甲基嘧啶-2-基、5-甲基嘧啶-2-基、5-氯嘧啶-2-基、5-氟嘧啶-2-基、5-溴嘧啶-2-基、5-乙基嘧啶-2基、5-甲氧基嘧啶-2基;吡啶-2-基、5-氯吡啶-2-基、5-氟吡啶-2-基、5-溴吡啶-2-基、4-氟苯基、4-溴苯基、4-氯苯基、4-甲基苯基、4-三氟甲氧基苯基、4,6-甲氧-1,3,5-三嗪-2-基。
本发明的含N杂环芳腙类衍生物I及其中间体的合成路线如下:
本发明所述含N杂环芳腙类衍生物I的合成方法分为以下步骤:
A.化合物含N杂环芳腙类衍生物I的制备:
(1)氮气保护条件下,将化合物1(1.0毫摩尔)溶于超干的四氢呋喃溶液中,之后在反应温度为-30摄氏度条件下,逐滴加入甲基格式试剂的四氢呋喃溶液(1.3毫摩尔)。加入完毕后,继续在-30摄氏度条件下搅拌2小时。薄层色谱检测反应完毕后,用饱和氯化铵溶液淬灭反应。用乙酸乙酯萃取,合并有机层,依次用水,饱和氯化钠溶液洗涤,无水硫酸钠干燥有机层,减压浓缩,柱层析石油醚∶乙酸乙酯=9∶1(体积比)纯化得到化合物2。
(2)将2-氯芳香环化合物3(1.0毫摩尔)溶于无水乙醇中,然后加入80%水合肼(6毫摩尔),加热回流条件下搅拌2-10小时,薄层色谱检测反应完毕后,静置冷却有固体析出,石油醚抽滤洗涤固体,干燥得到化合物4。
(3)将化合物2(1.0毫摩尔)溶于15毫升乙醇溶液中,之后加入化合物4(1.1毫摩尔)和催化量的冰乙酸(0.2毫摩尔),加热回流5-8小时。薄层色谱检测反应结束后,将反应液浓缩旋干,加入二氯甲烷和水,萃取合并有机层,有机层用饱和食盐水洗涤,加入无水硫酸钠干燥。柱层析石纯化得到含N杂环的芳腙类衍生物I。化合物I制备的量和反应容器的体积按相应比例扩大或缩小;
取代基Herto和Ar的定义如上所述。
B.含N杂环芳腙类衍生物I的用途:
本发明提供了所述含N杂环芳腙类衍生物I在制备杀真菌剂中的用途。
本发明提供了所述含N杂环芳腙类衍生物I在制备抗烟草花叶病毒剂中的用途。
本发明提供了所述含N杂环芳腙类衍生物I在制备植物激活剂用于诱导烟草抗烟草花叶病毒中的用途。
本发明提供了所述含N杂环芳腙类衍生物I在防治农业和林业以及园艺植物虫害中的用途。
本发明所述含N杂环芳腙类衍生物I及中间体可以制备农用杀菌组合物,该组合物包含权利要求1所述的含N杂环的芳腙类衍生物I作为活性成分,活性成分的含量为0.1到99.9%重量,99.9到0.1%重量的固体或液体助剂,及任选0到25%重量的表面活性剂。
本发明所述含N杂环芳腙类衍生物I和其他商品杀菌剂复配作为活性成分,含N杂环的芳腙类衍生物I与其他商品杀菌剂的比例为质量百分比1%∶99%到99%∶1%,活性成分的含量为1到99%重量,99到1%重量的固体或液体助剂。
本发明所述含N杂环芳腙类衍生物I和其他商品杀虫、杀螨剂复配作为活性成分,含N杂环的芳腙类衍生物I与其他商品杀虫、杀螨的比例为质量百分比1%∶99%到99%∶1%,活性成分的含量为1到99%重量,99到1%重量的固体或液体助剂。
本发明所述含N杂环芳腙类衍生物I和其他商品抗植物病毒剂复配作为活性成分,含N杂环的芳腙类衍生物I与其他商品抗植物病毒剂的比例为质量百分比1%∶99%到99%∶1%,活性成分的含量为1到99%重量,99到1%重量的固体或液体助剂。
本发明所述含N杂环芳腙类衍生物I的生物活性测定如下:
本发明的含N杂环芳腙类衍生物I的杀菌活性测定:
本发明的含N杂环芳腙类衍生物I的杀菌或抑菌活性采用菌体生长率测定法,具体步骤为:取1.8毫克样品溶解在2滴二甲基亚砜中,然后用含有一定量吐温20乳化剂的水溶液稀释至500微克/毫升的药剂,将供试药剂在无菌条件下各吸取1毫升于培养皿内,再分别加入9毫升PDA培养基,摇匀后制成50微克/毫升含药平板,以添加1毫升灭菌水的平板做空白对照,用直径4毫米的打孔器沿菌丝外缘切取菌盘,移至含药平板上,呈等边三角形摆放,每处理重复3次,将培养皿放在24±1摄氏度恒温培养箱内培养,待对照菌落直径扩展到2-3厘米后调查各处理菌盘扩展直径,求平均值,与空白对照比较计算相对抑菌率,供试菌种为我国农业生产中田间实际发生的大部分典型植物病原菌的种属,其代号和名称如下:A.s:番茄早疫病菌,拉丁名为:Alternaria solani、B.c:黄瓜灰霉病菌,拉丁名为:Botrytiscinerea、C.a:花生褐斑病菌,拉丁名为:Cercospora arachidicola、G.z:小麦赤霉病菌,拉丁名为:Gibberella zeae、P.p:苹果轮纹病菌,拉丁名为:Physalospora piricola、R.s:水稻纹枯病菌,拉丁名为:Rhizoctonia solani、S.s:油菜菌核病菌,拉丁名为:Sclerotiniasclerotiorum、P.o:稻瘟病病菌Pyricularia oryzae。
本发明的有益效果是:对含N杂环芳腙类衍生物I进行了先导优化,并对含N杂环芳腙类衍生物I进行了抑菌活性的筛选。
本发明通过特定制备和生物活性测定实施例更加具体说明含N杂环苯腙类衍生物I的合成与生物活性及应用,所述实施例仅用于具体说明本发明而非限制本发明,尤其是生物活性仅是举例说明,而非限制本专利,具体实施方式如下:
实施例1:化合物I-1的制备:
(1)氮气保护条件下,将化合物1(3克,12.44毫摩尔)溶于超干的四氢呋喃溶液中,之后在反应温度为-30摄氏度条件下,逐滴加入甲基格式试剂的四氢呋喃溶液(3摩尔/升,5.39毫升,16.18毫摩尔)。加毕后,继续在-30摄氏度条件下搅拌2小时。薄层色谱检测反应完毕后,用饱和氯化铵溶液(40毫升)淬灭反应,乙酸乙酯(3×40毫升)萃取,合并有机层,依次用水(50毫升),饱和氯化钠溶液(50毫升)洗涤,无水硫酸钠干燥有机层,减压浓缩,柱层析石油醚/乙酸乙酯(9∶1,体积比)纯化得到淡黄色固体化合物2,1.22克,收率50%。
(2)在100毫升单口圆底烧瓶中加入572.65毫克,5毫摩尔的2-氯嘧啶,将其溶于15毫升乙醇中。之后,用注射器加入1501.8毫克,30毫摩尔80%水合肼,混合液在100摄氏度下加热回流,薄层色谱检测反应完毕;反应完成后,室温冷却,有固体析出,抽滤,用石油醚洗涤,干燥得白色固体2-肼基嘧啶,500毫克,收率为90%。
(3)在100毫升单口圆底烧瓶中加入392.09毫克,2毫摩尔的3,4-二氯异噻唑-5-乙酮,溶于5毫升乙醇中,之后加入264.29毫克,2.4毫摩尔的2-肼基嘧啶,混合液在80摄氏度下加热5小时;薄层色谱检测反应完成后,浓缩除去溶剂,向反应液中加入10毫升的水,分离出水层用二氯甲烷萃取三遍(3×10毫升),合并有机层用饱和氯化钠溶液洗涤,无水硫酸钠干燥;浓缩除去溶剂,用石油醚/乙酸乙酯(5∶1,体积比)洗脱剂柱层析纯化得浅黄色固体I-1,收率65%。
实施例2:本发明的杂环苯腙类衍生物I的抑菌活性测定结果:
本发明测试的常见植物病原真菌代号和名称如下:A.s:番茄早疫病菌,拉丁名为:Alternaria solani、B.c:黄瓜灰霉病菌,拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,拉丁名为:Cercospora arachidicola、G.z:小麦赤霉病菌,拉丁名为:Gibberellazeae、P.p:苹果轮纹病菌,拉丁名为:Physalospora piricola、R.s:水稻纹枯病菌,拉丁名为:Rhizoctonia solani、S.s:油菜菌核病菌,拉丁名为:Sclerotinia sclerotiorum、P.o:稻瘟病病菌Pyricularia oryzae。这些菌种具有代表性,能够代表农业生产中田间发生的大部分病原菌的种属。
菌体生长率法测定结果见表2,表2表明,在50微克/毫升时,本发明合成的所有化合物均有不同程度的杀菌活性;商品化的嘧菌腙是与本发明专利化学结构最接近的商品化的杀菌剂。本发明以嘧菌腙做阳性对照开展了新化合物生物活性的测定;结果表明:对于番茄早疫病菌,本发明的化合物I-3、I-13、I-1、I-19、I-22的抑制率在50%以上,其中I-19的抑制率达到81.3%,对照药嘧菌腙的抑制率为98.9%;对于黄瓜灰霉病菌:化合物I-1、I-2、I-10、I-12、I-13、I-14、I-15、I-17的杀菌活性均在60%以上,其中化合物I-1、I-2、I-14、I-15的抑制率达到80%,对照Ferimzone的抑制率为100%;对于花生褐斑病菌:化合物I-14、I-15、I-17、I-19的杀菌活性均在60%以上,其中化合物I-14的抑制率最高,为77.1%,对照药抑制率为100%;对于小麦赤霉病菌:化合物I-14、I-16、I-17、I-19、I-22、I-23抑制率均在50%以上,尤其化合物I-17和I-19的杀菌活性分别为82.3%和80.4%,高于阳性对照药Ferimzone 51.1%;对于苹果轮纹病:化合物I-1、I-13、I-14、I-15、I-16、I-17、I-19的杀菌活性均在50%以上,其中化合物I-1、I-13、I-14、I-15的杀菌活性与阳性对照Ferimzone(75%)相当;对于立枯丝核病菌:化合物I-1、I-2、I-4、I-7、I-12、I-13、I-14、I-15、I-16、I-17、I-19、I-22、I-24的杀菌活性均在60%以上,其中化合物I-13、I-14、I-22、I-24的杀菌活性均在80%以上,I-13(91.2%)的杀菌活性与对照药Ferimzone(90%)相当;对油菜菌核病菌:化合物I-17的杀菌活性为79.9%,远高于阳性对照Ferimzone(31.5%);对于稻瘟病病菌:化合物I-14、I-1、I-22的杀菌活性在60%以上,I-17、I-22的杀菌活性在70%以上,对照药嘧菌腙的杀菌活性为100%。综上所述,化合物I-19、I-17、I-13、I-14、I-15、I-1表现出广谱的杀菌活性;本发明由于杂环基团的引入,目标分子取得了意料之外的高活性。
实施例3:本发明的含N杂环芳腙类衍生物I在制备农药组合物中的应用:
本发明的含N杂环芳腙类衍生物I制备农药组合物,该组合物含本发明的含N杂环芳腙类衍生物I或其中间体为活性成分,活性成分的质量百分含量为0.1%到99.9%,固体或液体助剂的质量百分含量为99.9%到0.1%,体系还含有任选0到50%质量百分含量的表面活性剂。
实施例4:本发明的含N杂环芳腙类衍生物I在制备农药复配组合物中的应用:
本发明的含N杂环芳腙类衍生物I及其中间体可以和其他商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂复配制备农药复配组合物,该复配组合物包含本发明的含N杂环芳腙类衍生物I及其中间体和商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂作为活性成分,本发明的含N杂环芳腙类衍生物I及其中间体与其他商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂的比例为质量百分比1%∶99%到99%∶1%,活性成分的质量百分含量为0.1%到99.9%,99.9%到0.1%质量百分含量的固体或液体助剂,以及任选0到50%质量百分含量的表面活性剂。
实施例5:本发明的含N杂环芳腙类衍生物I与杀虫剂组合在防治农业和林业以及园艺植物虫害中的应用:
本发明的含N杂环芳腙类衍生物I与商品杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害,所述商品杀虫剂选自:烯虫酯、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、七氟甲醚菊酯、氯氟醚菊酯、高效氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、β-氟氯氰菊酯、λ-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、多氟脲、氟螨脲、双苯氟脲、氟啶脲、嗪虫脲、双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、敌敌畏、喹硫磷、哒嗪硫磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、三唑锡、噻嗪酮、杀虫单、杀虫双、氯虫酰胺、四氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、丁烯氟虫腈、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素、戊吡虫胍;本发明的含N杂环芳腙类衍生物I在所述杀虫组合物中的质量百分含量是1%-90%,本发明的含N杂环芳腙类衍生物I与前述商品杀虫剂的比例为质量百分比1%∶99%到99%∶1%;所述杀虫组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀虫组合物适用的植物虫害选自:草地贪夜蛾、红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫;所述杀虫组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例6:本发明的含N杂环芳腙类衍生物I与杀菌剂组合在防治农业和林业以及园艺植物病害中的应用:
本发明的含N杂环芳腙类衍生物I与商品杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害,所述商品杀菌剂选自:苯并噻二唑、噻酰菌胺、甲噻诱胺、DL-β-氨基丁酸、异噻菌胺、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、萎锈灵、氧化萎锈灵、麦锈灵、甲呋酰胺、灭锈胺、氟酰胺、呋吡菌胺、噻呋酰胺、啶酰菌胺、吡噻菌胺、吡唑萘菌胺、联苯吡菌胺、氟吡菌酰胺、氟唑环菌胺、氟唑菌酰胺、氟唑菌苯胺、苯丙烯氟菌唑、异丙噻菌胺、氟唑菌酰羟胺、氟苯醚酰胺、氟醚菌酰胺、双炔酰菌胺、苯酰菌胺、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、丰索磷、虫线磷、除线磷、丁硫环磷、杀线威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑;本发明的含N杂环芳腙类衍生物I在所述杀菌组合物中总的质量百分含量是1%-90%,本发明的含N杂环芳腙类衍生物I与前述商品杀菌剂的量百分比为1%∶99%到99%∶1%;所述杀菌组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀菌组合物适用的植物病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病;所述杀菌组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例7:本发明的含N杂环芳腙类衍生物I与抗植物病毒剂组合在防治农业和林业以及园艺植物病毒病害中的应用:
本发明的含N杂环芳腙类衍生物I与商品抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害,所述商品抗病毒药剂选自:苯并噻二唑、噻酰菌胺、异噻菌胺DL-β-氨基丁酸、N-氰甲基-2-氯异烟酰胺、烯丙异噻唑、病毒唑、安托芬、宁南霉素、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈霉素、盐酸吗啉胍;本发明的含N杂环芳腙类衍生物I在所述抗病毒组合物中总的质量百分含量是1%-90%,本发明的含N杂环芳腙类衍生物I与前述商品抗植物病毒剂的比例为质量百分比1%∶99%到99%∶1%;所述抗病毒组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述抗病毒组合物防治的病毒病害选自:水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;所述抗病毒组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例8:本发明的含N杂环芳腙类衍生物I与杀螨剂组合在防治农业和林业以及园艺植物螨害中的应用:
本发明的含N杂环芳腙类衍生物I与商品杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害,所述商品杀螨剂选自:敌敌畏、庚烯磷、速灭磷、二溴磷、嘧啶磷、氯甲亚胺硫磷、乙硫磷、虫螨畏、伏杀硫磷、甲基嘧啶硫磷、喹硫磷、蚜灭多、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、丁硫速灭威、蜱虱威、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵;本发明的含N杂环芳腙类衍生物I在所述杀螨组合物中总的质量百分含量是1%-90%,本发明的含N杂环芳腙类衍生物I与所述商品杀螨剂的比例为质量百分比1%∶99%到99%∶1%;所述杀螨组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀螨组合物防治的螨害选自:螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨,这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨;所述杀螨组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
工业实用性
本发明提供一类含N杂环芳腙类衍生物。本发明所述衍生物能够调控农业、园艺和卫生以及林业植物害虫和植物病原物的生物活性,可用于农业领域、园艺领域、林业领域杀虫、杀螨、杀菌、抗植物病毒、诱导植物产生抗病性,具有较好的经济价值和应用前景。
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表2本发明的含N杂环芳腙类衍生物I的抑菌活性(50微克/毫升的抑制率/%)
序号 | 化合物编号 | A.s | B.c | C.a | G.z | P.p | R.s | S.s | P.o |
1 | I-1 | 34.4 | 88.5 | 40.0 | 32.7 | 72.5 | 65.8 | 22.4 | 22.9 |
2 | I-2 | 23.9 | 85.6 | 27.2 | 33.5 | 41.6 | 72.1 | 30.7 | 15.3 |
3 | I-3 | 67.0 | 50.4 | 35.5 | 44.5 | 50.4 | 58.0 | 21.9 | 0 |
4 | I-4 | 38.1 | 50.5 | 36.4 | 37.4 | 0 | 62.0 | 48.8 | 50.5 |
5 | I-5 | 20.3 | 49.4 | 17.5 | 33.8 | 23.1 | 45.2 | 20.7 | 30.1 |
6 | I-6 | 46.4 | 25.6 | 27.8 | 50.8 | 40.6 | 30.7 | 27.6 | 0 |
7 | I-7 | 28.1 | 45.3 | 23.1 | 35.0 | 26.4 | 64.8 | 25.3 | 28.2 |
8 | I-8 | 27.1 | 7.0 | 18.4 | 9.0 | 44.4 | 38.2 | 18.9 | 31.9 |
9 | I-9 | 19.6 | 7.5 | 22.8 | 17.2 | 38.6 | 37.5 | 16.5 | 29.7 |
10 | I-10 | 14.6 | 66.3 | 19.7 | 28.1 | 45.2 | 46.8 | 14.9 | 46.4. |
11 | I-11 | 19.7 | 48.6 | 16.0 | 12.8 | 13.6 | 27.9 | 28.1 | 15.8 |
12 | I-12 | 25.5 | 71.6 | 27.8 | 30.0 | 35.3 | 72.6 | 24.9 | 29.2 |
13 | I-13 | 53.2 | 64.3 | 40.2 | 32.2 | 73.6 | 91.2 | 47.2 | 36.1 |
14 | I-14 | 67.3 | 81.2 | 77.1 | 51.9 | 74.5 | 86.5 | 49.6 | 64.8 |
15 | I-15 | 76.1 | 82.9 | 68.8 | 41.8 | 77.4 | 71.2 | 48.7 | 68.0 |
16 | I-16 | 44.4 | 42.6 | 24.7 | 52.7 | 50.2 | 73.7 | 47.2 | 30.6 |
17 | I-17 | 44.4 | 74.9 | 70.5 | 82.3 | 64.4 | 73.0 | 79.9 | 77.2 |
18 | I-18 | 40.2 | 27.3 | 42.1 | 40.2 | 37.7 | 19.5 | 37.3 | 47.9 |
19 | I-19 | 81.3 | 66.7 | 62.8 | 80.4 | 60.6 | 79.3 | 33.2 | 56.0 |
20 | I-20 | 5.8 | 9.7 | 7.0 | 5.1 | 3.9 | 27.0 | 35.6 | 41.4 |
21 | I-21 | 34.4 | 40.7 | 33.4 | 56.1 | 40.8 | 58.3 | 17.0 | 22.5 |
22 | I-22 | 74.0 | 26.0 | 66.8 | 63.3 | 21.5 | 88.1 | 37.1 | 86.0 |
23 | I-23 | 29.7 | 39.1 | 62.2 | 46.5 | 22.3 | 50.3 | 27.4 | 20.6 |
24 | I-24 | 41.5 | 27.7 | 0 | 43.2 | 25.0 | 81.7 | 45.9 | 73.2 |
19 | Ferimzone | 98.9 | 100 | 100 | 51.1 | 75.2 | 90.1 | 31.5 | 100 |
A.s:番茄早疫病菌,拉丁名为:Alternaria solani、B.c:黄瓜灰霉病菌,拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,拉丁名为:Cercospora arachidicola、G.z:小麦赤霉病菌,拉丁名为:Gibberella zeae、P.p:苹果轮纹病菌,拉丁名为:Physalosporapiricola、P.s:水稻纹枯病菌,拉丁名为:Pellicularia sasakii、S.s:油菜菌核病菌,拉丁名为:Sclerotinia sclerotiorumalis、P.o:水稻稻瘟病菌,拉丁名为:Pyriculariaoryzae.
Claims (6)
1.一类含N杂环芳腙类衍生物,其特征在于同时含有具有诱导抗病活性杂环和腙的结构,具有如式I所示的结构通式:
其中,
当Hetro为3,4-二氯异噻唑-5-基时,Ar选自:嘧啶-2-基、4,6-二甲基嘧啶-2-基、5-甲基嘧啶-2-基、5-氯嘧啶-2-基、5-氟嘧啶-2-基、5-溴嘧啶-2-基、5-乙基嘧啶-2基、5-甲氧基嘧啶-2基;吡啶-2-基、5-氯吡啶-2-基、5-氟吡啶-2-基、5-溴吡啶-2-基、4-氟苯基、4-溴苯基、4-氯苯基、4-甲基苯基、4-三氟甲氧基苯基、4,6-甲氧-1,3,5-三嗪-2-基;
当Hetro为4-甲基1,2,3-噻二唑-5-基时,Ar选自:4-溴苯基、4-三氟甲氧基苯基;
当Hetro为苯并[d][1,2,3]噻二唑-7-基时,Ar选自:4-溴苯基、4-三氟甲氧基苯基;
当Hetro为2,6-二氯吡啶-4-基时,Ar选自:4-溴苯基、4-三氟甲氧基苯基。
2.根据权利要求1所述N杂环芳腙类衍生物I的具体合成路线为:
所述取代基Hetro和Ar的定义如权利要求1所述。
3.根据权利要求2所述N杂环芳腙类衍生物I的具体合成方法为:
A.化合物2的制备:
氮气保护条件下,将化合物1溶于超干的四氢呋喃溶液中,之后在反应温度为-30摄氏度条件下,逐滴加入甲基溴化镁的四氢呋喃溶液3.0摩尔/升,加入完毕后,继续在-30摄氏度条件下搅拌2小时,薄层色谱检测反应完毕后,用饱和氯化铵溶液淬灭反应,用乙酸乙酯萃取,合并有机层,依次用水,饱和氯化钠溶液洗涤,无水硫酸钠干燥有机层,减压浓缩,柱层析纯化得到化合物2;化合物1和化合物2结构通式中的取代基Hcrto的定义如权利要求1;
B.化合物4的制备:
将2-氯芳香环化合物3溶于无水乙醇中,然后加入80%水合肼,加热回流条件下搅拌2-10小时,薄层色谱检测反应完毕后,静置冷却有固体析出,石油醚抽滤洗涤固体,干燥得到化合物4;化合物3和化合物4结构通式中的取代基Ar的定义如权利要求1;
C.化合物I的制备:
将2.0毫摩尔化合物2溶于15毫升乙醇溶液中,之后加入2.2毫摩尔化合物3和0.4毫摩尔催化量的冰乙酸,加热回流5-8小时,薄层色谱检测反应结束后,将反应液浓缩旋干,加入二氯甲烷和水萃取,合并有机相,有机相用饱和食盐水洗涤,加入无水硫酸钠干燥,柱层析纯化得到含N杂环的芳腙类衍生物I;化合物I结构通式中的取代基Herto和Ar的定义如权利要求1。
4.权利要求1所述的含N杂环的芳腙类衍生物I在制备农用杀真菌剂中的用途,所述真菌选自:番茄早疫病菌,拉丁名为:Alternaria solani、黄瓜灰霉病菌,拉丁名为:Botrytiscinerea、花生褐斑病菌,拉丁名为:Cercospora arachidicola、小麦赤霉病菌,拉丁名为:Gibberella zeae、苹果轮纹病菌,拉丁名为:Physalospora piricola、水稻纹枯病菌,拉丁名为:Rhizoctonia solani、油菜菌核病菌,拉丁名为:Sclerotinia sclerotiorum、稻瘟病病菌Pyricularia oryzae。
5.一种农用杀菌组合物,权利要求1所述的含N杂环的芳腙类衍生物I用于制备农用杀菌组合物,该组合物的活性成分为权利要求1所述的含N杂环的芳腙类衍生物I,活性成分的含量为0.1%到99.9%的重量百分比,该组合物的固体或液体助剂含量为99.9%到0.1%的重量百分比,该组合物的表面活性剂含量为0%到25%的重量百分比。
6.一种农用杀菌复配组合物,其活性成分为权利要求1所述的含N杂环的芳腙类衍生物I和其他商品杀菌剂,含N杂环的芳腙类衍生物I与其他商品杀菌剂的比例为质量百分比1%∶99%到99%∶1%,活性成分的含量为1%到99%的重量百分比,固体或液体助剂的含量为99%到1%的重量百分比。
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---|
Synthesis, spectral characterization and in vitro antimicrobial activity of some new azopyridine derivatives;Abuo-Melha, Hanaa 等;Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy;第89卷;第123-128页 * |
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