CN117964555A - 一类含苯醚键的双酰胺类衍生物及其制备方法和用途 - Google Patents
一类含苯醚键的双酰胺类衍生物及其制备方法和用途 Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 title claims description 48
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Abstract
本发明提供了苯醚键的双酰胺类衍生物及其制备方法和用途,其化学结构通式见式I:I:
Description
技术领域
本发明的技术方案涉及含苯醚键的双酰胺类衍生物。
背景技术
几十年来,农药为人类食物的供应和对人类的安全(防御疾病传播和控制疾病传播范围等)和健康(杀灭病菌和控制病原产生等方面)起到了不可磨灭的作用,极大程度上减少了财产损失,同时是确保农业稳产、增收不可或缺的生产资料,也是一个十分重要的战略物资。但是近些年,害虫的抗性问题以及传统农药存在严重的环境污染等问题,这对农药的开发提出了更高的要求。因此需要不断研发高效、低毒、环保、低成本和具有新型作用方式的杀虫剂品种以满足现代社会的需求。
2001年,邻甲酰胺基苯甲酰胺类化合物由杜邦公司研制成功,经过研究证明发现该类化合物是一类鱼尼丁受体杀虫剂。经研究发现,邻甲酰胺基苯甲酰胺类化合物具有更广谱的杀虫活性,除了对鳞翅目害虫具有很好的杀虫效果,而且还对双翅目、半翅目、鞘翅目等害虫也有很高的杀虫活性。近些年,美国杜邦公司、拜耳农科、先正达以及国内的很多研究机构先后申请了大量的专利,报道了大量的化合物。如:WO 2003016300、WO2004067528、WO2005118552 A2、WO 2007031213、WO 2008137970、CN 103467380 A。
新农药的创制方法和策略多种多样,其中活性片段的拼接是一种高效的新药研发手段。苯醚键在目前多种上市的,作用于不同靶标的杀虫剂中都存在,比如,作用于钠离子通道的拟除虫菊酯类杀虫剂氯菊酯和醚菊酯;作用于线粒体三磷酸腺苷合成酶的抑制剂炔螨特;作用在线粒体电子传递复合体抑制剂唑虫酰胺等。因此我们在与吡唑环相连的邻甲酰胺基苯甲酰胺类化合物苯环的4位引入醚键,同时,醚键的引入还能调节化合物的理化性质。
本发明的目的在于针对上述技术分析,提供一种能改善原有化合物抗药性和提高杀虫活性并扩大杀虫谱的苯醚键的双酰胺类衍生物及其制备方法和应用。
发明内容
本发明所要解决的技术问题是:提供一类新的苯醚键的双酰胺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苯醚键的双酰胺类衍生物的化学结构通式如I所示:
其中,R1选自:氯、溴;R2选自:甲基、乙基、异丙基、三氟乙基;R3选自:溴、三氟甲基、三氟乙氧基;R4选自:取代烷基、取代烯基、取代炔基、脂肪环烷基、脂肪环烯基、取代苯基、取代杂环芳基;R5选自:甲基、氯;
取代基优选:
R1选自:氯;R2选自:甲基、乙基、异丙基、三氟乙基;R3选自:溴、三氟甲基、三氟乙氧基;R4选自:三氟甲基、三氟乙基、甲基、苄基、丙炔基、丙烯基、亚甲己烷、亚甲基环戊烷、1-氯丙基;R5选自:甲基、氯。
本发明的苯醚键的双酰胺类衍生物I及其中间体的合成路线如下:
化合物I的合成路线
本发明所述含苯醚键的双酰胺类衍生物的双酰胺类衍生物I的合成方法分为以下步骤:
A化合物A的制备:
中间体A由取代苯肼在乙醇钠作用下与马来酸二乙酯在乙醇中回流关环得到:
将卤素取代的苯肼溶于乙醇中,加入乙醇钠和马来酸二乙酯在80摄氏度下反应2小时,减压浓缩除去溶剂,用饱和碳酸氢钠水溶液萃取,柱层析纯化得到化合物A;化合物A结构通式中的取代基R4的定义如前所述;;
B.化合物B的制备:
中间体B由中间体A通过三溴氧磷和三乙胺在乙腈中回流制备:
将化合物A溶于乙腈中,加入三溴氧磷和三乙胺,在70摄氏度下反应2小时,减压除去溶剂,用饱和食盐水溶液萃取,柱层析纯化得到化合物B;化合物A结构通式中的取代基R3、R4的定义如前所述;
C.化合物C的制备:
中间体C由中间体B通过过硫酸钾和浓硫酸在乙腈中加热回流制备:将化合物B溶于乙腈,加入浓硫酸和过硫酸钾,80摄氏度条件下反应2小时,减压浓缩除去溶剂,用乙酸乙酯稀释后与饱和食盐水萃取,收集有机相减压除去溶剂后,柱层析纯化得到化合物C;化合物C结构通式中的取代基R3、R4的定义如前所述;
D.化合物D的制备:
中间体D通过一水合氢氧化锂对中间体C进行水解反应制备:
将化合物C溶于乙醇和水的混合溶剂(1∶1),加入氢氧化锂,室温下搅拌2小时,减压除去乙醇后加少量的水,用1摩尔/升的盐酸水溶液调pH至1-2左右,析出大量的白色固体,抽滤,得到化合物D;化合物D结构通式中的取代基R3、R4的定义如前所述;
E.化合物I的制备:
目标化合物I由中简体D和中间体E通过酰氯法发生酰胺缩合反应制备:
将化合物D溶于二氯甲烷中,加入草酰氯和N,N-二甲基甲酰胺,室温条件下搅拌3小时,减压除去溶剂得到酰氯备用;在冰浴条件下将化合物E溶于四氢呋喃中,加入N,N-二异丙基乙胺,随后将备用的酰氯溶于四氢呋喃中缓慢的加入体系,滴加完成后室温搅拌1.5小时,减压除去溶剂,用二氯甲烷稀释后分别用1摩尔/升盐酸水溶液,饱和碳酸氢钠水溶液和饱和食盐水萃取,收集有机相,减压除去有机相,并用二氯甲烷和正己烷重结晶,抽滤,得到白色固体I;化合物D结构通式中的取代基R1、R2、R3、R4、R5的定义如前所述;
F.化合物I的在制备农药组合物种的用途:
本发明提供了所述含苯醚键的双酰胺类衍生物I在防治农业和林业以及园艺植物虫害中的用途。
本发明提供了所述含苯醚键的双酰胺类衍生物I在制备农用杀虫剂的用途,所述杀虫剂防治的害虫为鳞翅目类、鞘翅目类、同翅目类、双翅目类及直翅目类害虫。
本发明提供了所述含苯醚键的双酰胺类衍生物I在制备农用杀虫剂的用途,所述杀虫剂防治的害虫为东方粘虫和小菜蛾。
本发明提供了所述含苯醚键的双酰胺类衍生物I作为活性成分;该组合物包含0.1%到99.9%重量的活性成分,99.9%到0.1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
本发明提供了所述含苯醚键的双酰胺类衍生物I的用途,其特征在于:用于制备农用化学杀虫剂,所用衍生物为其任何比例的混合物及其在农业中可接受的盐,还可作为活性成分配以农业可以接受的助剂组成的农药组合物用于昆虫的防治。
G.化合物I的在制备农药复配组合物种的用途:
本发明提供了所述含苯醚键的双酰胺类衍生物I与农业化学品共同施用;所述农业化学品选自:商品杀虫剂、商品杀菌剂、商品抗植物病毒剂、商品植物激活剂中的一种或几种。
本发明提供了一种农用杀虫复配组合物,其包含权本发明所述的含苯醚键的双酰胺类衍生物I和其他商品杀虫剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物I与其他商品杀虫、杀螨剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
本发明提供了一种农用杀菌复配组合物,其包含权本发明所述的含苯醚键的双酰胺类衍生物I和其他商品杀菌剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物I与其他商品杀菌剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
本发明提供了一种抗植物病毒剂复配组合物,其包含权本发明所述的含苯醚键的双酰胺类衍生物I和其他商品抗植物病毒剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物I与其他商品抗植物病毒剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
本发明提供了一种植物激活剂复配组合物,其包含权本发明所述的含苯醚键的双酰胺类衍生物I和其他商品植物激活剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物I与其他商品植物激活剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
本发明所述含苯醚键的双酰胺类衍生物I的生物活性测定如下:
H.本发明的所述含苯醚键的双酰胺类衍生物I的杀虫活性测定:
利用本发明提供的衍生物进行测试,验证对害虫生物活性评价:
将本发明提供的任一种衍生物溶于溶剂、水和表面活性剂,混合成为均一水相,使用时可用水稀释至任何所需的浓度,测试对象和测试方法如下:
(1)对东方粘虫的生物活性评价:供试昆虫是东方粘虫(Mythimna separataWalker),室内用玉米叶饲养的正常群体。粘虫采用浸叶法,浸渍苗期玉米叶于已配置好的溶液中,晾干后放入直径7厘米培养皿中,接入4龄幼虫,每个浓度重复3次;对照用丙酮溶液浸渍玉米叶饲养幼虫,24小时、48小时、72小时后观察试验结果。
(2)对小菜蛾的生物活性评价:供试昆虫是小菜蛾2龄幼虫(Plutellaxylostella),为室内正常饲养的正常群体;采用浸叶法,用镊子浸渍甘蓝叶片于已配置好的溶液中,时间2-3秒,甩掉余液;每次1片,每个样品共3片;待药液干后,放入10厘米长的直型试管内,接入2龄小菜蛾幼虫,用纱布盖好管口;将试验处理置于标准处理室内,24小时、48小时、72小时后观察试验结果。
本发明的有益效果是:对含苯醚键的双酰胺类衍生物I进行了先导优化,并对含苯醚键的双酰胺类衍生物进行了杀虫活性的筛选。
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苯醚键的双酰胺类衍生物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:N-(4-氯-2-甲基-6-(甲基氨基甲酰基)苯基)-1-(2,6-二氟苯基)-3-乙氧基-1H-吡唑-5-甲酰胺,其合成步骤如下:
步骤1:制备2-(2-氯-4-(三氟甲氧基)苯基)-5-氧代吡唑烷-3-羧酸乙酯
将金属钠(1.1克)加到60毫升乙醇中,待金属钠反应完全之后,再加入(2-氯-4-三氟甲氧基苯基)肼(3.0克)。加热到回流后,向体系中滴入马来酸二乙酯(4.5克)。继续回流3小时后,原料反应完毕。淬灭后,后处理得2-(2-氯-4-(三氟甲氧基)苯基)-5-氧代吡唑烷-3-羧酸乙酯。
步骤2:制备3-溴-1-(2-氯-4-(三氟甲氧基)苯基)-4,5-二氢-1H-吡唑-5-甲酸乙酯
将2-(2-氯-4-(三氟甲氧基)苯基)-5-氧代吡唑烷-3-羧酸乙酯(2.0克)加入到20毫升的乙腈中,然后依次加入三溴氧磷和三乙胺,回流3小时后,后处理得3-溴-1-(2-氯-4-(三氟甲氧基)苯基)-4,5二氢-1H-吡唑-5-甲酸乙酯。
步骤3:制备3-溴-1-(2-氯-4-(三氟甲氧基)苯基)-1H-吡唑-5-甲酸乙酯
将3-溴-1-(2-氯-4-(三氟甲氧基)苯基)-4,5-二氢-1H-吡唑-5-甲酸乙酯(0.86克)溶于10毫升乙腈,依次加入过硫酸钾和浓硫酸,加热反应3小时,最后处理后得3-溴-1-(2-氯-4-(三氟甲氧基)苯基)-1H-吡唑-5-甲酸乙酯。
步骤4:制备3-溴-1-(2-氟-4-(三氟甲氧基)苯基)-1H-吡唑-5-羧酸
将化合物3-溴-1-(2-氯-4-(三氟甲氧基)苯基)-1H-吡唑-5-甲酸乙酯(1.0克)溶于20毫升乙醇中,再加入溶有氢氧化锂(0.5克)的水溶液10毫升,室温反应12小时后,后处理得3-溴-1-(2-氟-4-(三氟甲氧基)苯基)-1H-吡唑-5-羧酸。
步骤5:制备3-溴-N-(4-氯-2-甲基-6-(甲基氨基甲酰基)苯基)-1-(2-氟-4(三氟甲氧基)苯基)-1H-吡唑-5-甲酰胺
将3-溴-1-(2-氟-4-(三氟甲氧基)苯基)-1H-吡唑-5-羧酸(100毫克)溶于3毫升二氯甲烷中,搅拌下加入草酰氯(68微升)和一滴无水N,N-二甲基甲酰胺,原料反应完毕后,减压浓缩除去溶剂,然后重新加入4毫升干燥的四氢呋喃,冰盐浴下,滴加到溶有2-氨基-5-氯-N,3-二甲基苯甲酰胺(80毫克)和N,N-二异丙基乙胺(70微升)的四氢呋喃溶液(5毫升)中。反应完毕后处理得3-溴-N-(4-氯-2-甲基-6-(甲基氨基甲酰基)苯基)-1-(2-氟-4(三氟甲氧基)苯基)-1H-吡唑-5-甲酰胺。
实施例2:本发明的苯醚键的双酰胺类衍生物I的杀虫活性测定结果:
本发明测试的常见鳞翅目昆虫名称如下:东方粘虫,其拉丁名为:Mythimnaseparata、小菜蛾,其拉丁名为:Plutella xylostella这些鳞翅目昆虫具有很好的代表性,能够代表农业生产中田间发生虫害的大部分昆虫。
对以上两种鳞翅目昆虫的杀虫测定结果见表2-表4,实验结果表明,所有的目标化合物对东方黏虫有中等到较好的杀虫活性,其中化合物A-1和A-3在0.1毫克/升的浓度下与氯虫酰胺都具有杀虫活性,化合物A-4-A-11至少在5毫克/升的浓度下有杀虫活性,而LC50值也表明化合物A-1和A-3与阳性对照氯虫酰胺的活性相当。对于小菜蛾,我们挑选对东方粘虫较好的化合物进行测试,根据LC50值我们发现化合物A-1比氯虫酰胺的杀虫活性高出3.2倍。
综合以上两种鳞翅目昆虫的杀虫活性结果,化合物A-1对东方粘虫的杀虫活性与对照药的活性相当,而对小菜蛾的杀虫活性却要比对照药氯虫酰胺高出了3.2倍。因此,化合物A-1具有超高效和杀虫谱广的特点,有希望成为杀虫剂的先导化合物。
实施例3:本发明的苯醚键的双酰胺类衍生物I在制备农药组合物中的应用:
本发明的苯醚键的双酰胺类衍生物I制备农药组合物,该组合物含本发明的苯醚键的双酰胺类衍生物I及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%,此外还含有任选0到50%质量百分含量的表面活性剂。
实施例4:本发明的苯醚键的双酰胺类衍生物I在制备农药复配组合物中的应用:
本发明的苯醚键的双酰胺类衍生物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苯醚键的双酰胺类衍生物的双酰胺类衍生物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,本发明的苯醚键的双酰胺类衍生物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:本发明的苯醚键的双酰胺类衍生物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:
本发明的苯醚键的双酰胺类衍生物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;本发明的苯醚键的双酰胺类衍生物I在所述杀虫组合物中的质量百分含量是1%-90%,本发明的苯醚键的双酰胺类衍生物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:本发明的苯醚键的双酰胺类衍生物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:
本发明的苯醚键的双酰胺类衍生物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、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;本发明的含苯醚键的双酰胺类衍生物的双酰胺类衍生物I在所述杀菌组合物中总的质量百分含量是1%-90%,本发明的含苯醚键的双酰胺类衍生物的双酰胺类衍生物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:本发明的苯醚键的双酰胺类衍生物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:
本发明的苯醚键的双酰胺类衍生物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、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;本发明的含苯醚键的双酰胺类衍生物的双酰胺类衍生物I在所述抗病毒组合物中总的质量百分含量是1%-90%,本发明的含苯醚键的双酰胺类衍生物的双酰胺类衍生物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:本发明的苯醚键的双酰胺类衍生物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:
本发明的苯醚键的双酰胺类衍生物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;本发明的含苯醚键的双酰胺类衍生物的双酰胺类衍生物I在所述杀螨组合物中总的质量百分含量是1%-90%,本发明的含苯醚键的双酰胺类衍生物的双酰胺类衍生物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。
实施例9:本发明的苯醚键的双酰胺类衍生物I与植物激活剂组合在防治农业和林业以及园艺植物螨害中的应用:
所述含苯醚键的双酰胺类衍生物I与所述植物免疫激活剂中的任意一种或两种组合形成植物免疫激活剂组合物用于防治农业和林业以及园艺植物病害;
所述植物激活剂药剂选自:苯并噻二唑、异噻菌胺、S-诱抗素、寡糖链蛋白、氨基寡糖素、香菇多糖、氟唑活化酯、低聚糖素、几丁聚糖、毒氟磷、DL-β-氨基丁酸、2,6-二氯异烟酸、N-氰甲基-2-氯异烟酰胺、烯丙异噻唑、甲噻诱胺、冠菌素、水杨酸、井冈霉素、超敏蛋白、昆布素、吡唑醚菌酯、烯丙异噻唑噻菌灵;
所述含含苯醚键的双酰胺类衍生物I在所述植物免疫激活剂组合物中总的质量百分含量是1%-90%;优选地,所述含苯醚键的双酰胺类衍生物I与所述植物免疫激活剂的比例为质量百分比1%∶99%到99%∶1%;
所述植物免疫激活剂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;
所述抗植物免疫激活剂组合物防治的病害选自: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、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;
所述植物免疫激活剂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
本发明提供一类苯醚键的双酰胺类衍生物。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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Claims (10)
1.一类含苯醚键的双酰胺类衍生物,其特征在于具有如式I的化学结构:
其中,R1选自:氯、溴;R2选自:甲基、乙基、异丙基、三氟乙基;R3选自:溴、三氟甲基、三氟乙氧基;R4选自:取代烷基、取代烯基、取代炔基、脂肪环烷基、脂肪环烯基、取代苯基、取代杂环芳基;R5选自:甲基、氯;
取代基优选:
R1选自:氯;R2选自:甲基、乙基、异丙基、三氟乙基;R3选自:溴、三氟甲基、三氟乙氧基;R4选自:三氟甲基、三氟乙基、甲基、苄基、丙炔基、丙烯基、亚甲己烷、亚甲基环戊烷、1-氯丙基;R5选自:甲基、氯。
2.权利要求1所述的含苯醚键的双酰胺类衍生物的制备方法,其特征在于其合成步骤如下:
其中,R1选自:氯、溴;R2选自:甲基、乙基、异丙基、三氟乙基;R3选自:溴、三氟甲基、三氟乙氧基;R4选自:取代烷基、取代烯基、取代炔基、脂肪环烷基、脂肪环烯基、取代苯基、取代杂环芳基,R5选自:甲基、氯;
上述取代基优选:
R1选自:氯;R2选自:甲基、乙基、异丙基、三氟乙基;R3选自:溴、三氟甲基、三氟乙氧基;R4选自:三氟甲基、三氟乙基、甲基、苄基、丙炔基、丙烯基、亚甲己烷、亚甲基环戊烷、1-氯丙基;R5选自:甲基、氯;
具体合成方法分为以下步骤:
A.化合物A的制备:
中间体A由取代苯肼在乙醇钠作用下与马来酸二乙酯在乙醇中回流关环得到:
将卤素取代的苯肼溶于乙醇中,加入乙醇钠和马来酸二乙酯在80摄氏度下反应2小时,减压浓缩除去溶剂,用饱和碳酸氢钠水溶液萃取,柱层析纯化得到化合物A;化合物A结构通式中的取代基R4的定义如前所述;
B.化合物B的制备:
中间体B由中间体A通过三溴氧磷和三乙胺在乙腈中回流制备:
将化合物A溶于乙腈中,加入三溴氧磷和三乙胺,在70摄氏度下反应2小时,减压除去溶剂,用饱和食盐水溶液萃取,柱层析纯化得到化合物B;化合物A结构通式中的取代基R3、R4的定义如前所述;
C.化合物C的制备:
中间体C由中间体B通过过硫酸钾和浓硫酸在乙腈中加热回流制备:将化合物B溶于乙腈,加入浓硫酸和过硫酸钾,80摄氏度条件下反应2小时,减压浓缩除去溶剂,用乙酸乙酯稀释后与饱和食盐水萃取,收集有机相减压除去溶剂后,柱层析纯化得到化合物C;化合物C结构通式中的取代基R3、R4的定义如前所述;
D.化合物D的制备:
中间体D通过一水合氢氧化锂对中间体C进行水解反应制备:
将化合物C溶于乙醇和水的混合溶剂(1∶1),加入氢氧化锂,室温下搅拌2小时,减压除去乙醇后加少量的水,用1摩尔/升的盐酸水溶液调pH至1-2左右,析出大量的白色固体,抽滤,得到化合物D;化合物D结构通式中的取代基R3、R4的定义如前所述;
E.化合物I的制备:
目标化合物I由中简体D和中间体E通过酰氯法发生酰胺缩合反应制备:
将化合物D溶于二氯甲烷中,加入草酰氯和N,N-二甲基甲酰胺,室温条件下搅拌3小时,减压除去溶剂得到酰氯备用;在冰浴条件下将化合物E溶于四氢呋喃中,加入N,N-二异丙基乙胺,随后将备用的酰氯溶于四氢呋喃中缓慢的加入体系,滴加完成后室温搅拌1.5小时,减压除去溶剂,用二氯甲烷稀释后分别用1摩尔/升盐酸水溶液,饱和碳酸氢钠水溶液和饱和食盐水萃取,收集有机相,减压除去有机相,并用二氯甲烷和正己烷重结晶,抽滤,得到白色固体I;化合物D结构通式中的取代基R1、R2、R3、R4、R5的定义如前所述。
3.权利要求1所述的含苯醚键的双酰胺类衍生物在制备农用杀虫剂的用途,所述杀虫剂防治的害虫为鳞翅目类、鞘翅目类、同翅目类、双翅目类及直翅目类害虫。
4.权利要求1所述的含苯醚键的双酰胺类衍生物在制备农用杀虫剂的用途,所述杀虫剂防治的害虫为东方粘虫和小菜蛾。
5.一种农用杀虫组合物,该组合物包含权利要求1所述的含苯醚键的双酰胺类衍生物作为活性成分;该组合物包含0.1%到99.9%重量的活性成分,99.9%到0.1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
6.根据权利要求1所述的含苯醚键的双酰胺类衍生物的应用,其特征在于:用于制备农用化学杀虫剂,所用衍生物为其任何比例的混合物及其在农业中可接受的盐,还可作为活性成分配以农业可以接受的助剂组成的农药组合物用于昆虫的防治。
7.一种农用杀虫、杀螨复配组合物,其包含权利要求1所述的含苯醚键的双酰胺类衍生物和其他商品杀虫、杀螨剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物与其他商品杀虫、杀螨剂的质量百分比为1%·99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
8.一种农用杀菌复配组合物,其包含权利要求1所述的含苯醚键的双酰胺类衍生物和其他商品杀菌剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物与其他商品杀菌剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
9.一种抗植物病毒剂复配组合物,其包含权利要求1所述的含苯醚键的双酰胺类衍生物和其他商品抗植物病毒剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物与其他商品抗植物病毒剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
10.一种植物激活剂复配组合物,其包含权利要求1所述的含苯醚键的双酰胺类衍生物和其他商品植物激活剂复配作为活性成分;活性成分含苯醚键的双酰胺类衍生物与其他商品植物激活剂的质量百分比为1%∶99%到99%∶1%,该复配组合物包含1%到99%重量的活性成分,99%到1%重量的固体或液体助剂,以及选自0到25%重量的表面活性剂。
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