CN113929696A - 一类酰基硫脲补骨脂素类衍生物及其制备方法和用途 - Google Patents
一类酰基硫脲补骨脂素类衍生物及其制备方法和用途 Download PDFInfo
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- CN113929696A CN113929696A CN202111351141.4A CN202111351141A CN113929696A CN 113929696 A CN113929696 A CN 113929696A CN 202111351141 A CN202111351141 A CN 202111351141A CN 113929696 A CN113929696 A CN 113929696A
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- Prior art keywords
- compound
- psoralen
- acyl thiourea
- stirring
- reaction
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- 238000002360 preparation method Methods 0.000 title claims abstract description 33
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- -1 acyl thiourea psoralen derivatives Chemical class 0.000 claims abstract description 147
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 104
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- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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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
- A01N47/08—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 the carbon atom having one or more single bonds to nitrogen atoms
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- A—HUMAN NECESSITIES
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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
- A01N47/08—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 the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Abstract
本发明提供了一类酰基硫脲补骨脂素类衍生物及其制备方法和用途,具体涉及一类酰基硫脲补骨脂素衍生物,其化学结构通式见式I:
Description
技术领域
本发明的技术方案属于农药领域,具体涉及一类酰基硫脲补骨脂素类化合物及其制备方法和用途。
背景技术
传统化学农药的滥用导致许多主要农作物的病原微生物和害虫产生抗药性、生态环境恶化,生物多样性水平降低等一系列问题,而以植物体内对病原菌具有拮抗性的化学物质为主要成分的植物源农药,因其具有低毒、低残留、对非靶标生物及环境安全的特点而越来越受到重视(于忻滢等.黑龙江农业科学,2021,(07),123-129.)。
补骨脂素是源于补骨脂中的呋喃香豆素类天然活性成分,具有抗肿瘤、抗炎、抗菌、抗抑郁、抗病毒和抗氧化等多种生理和药理活性(柯昌虎等.中南药学,2016,14(07),731-734.),是一种重要的植物源药物中间体,在食品、医药和农药等领域具有广泛的应用价值。已有研究表明补骨脂素作为活性成分制备得到的农业杀菌剂具有优异的杀菌活性,可应用在防治各种农作物的病害,特别适合于防治农业真菌病害,如:油菜菌核病、黄瓜枯萎病、小麦纹枯病、小麦赤霉病、水稻纹枯病等。
硫脲衍生物是一类重要的有机化工中间体,广谱的生物活性和良好的理化性质使得它被广泛应用于农药、医药、高分子等多个领域。而这其中酰基硫脲类化合物是脲类化合物中重要的一类衍生物,具有广泛的生物活性,如抗肿瘤、杀菌、抗炎、除草、杀虫等等(谭成侠等.有机化学,2013,33,2396-2401.)。
为寻找和发现更加高效、广谱、低毒、低生态风险且无交互抗性的农药先导及侯选化合物,本发明将酰基硫脲引入到补骨脂素的先导结构中,设计合成了一类酰基硫脲补骨脂素类衍生物,并进行了系统的生物活性的筛选和评价。
发明内容
本发明所要解决的技术问题是:提供一类新的酰基硫脲补骨脂素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酰基硫脲补骨脂素类化合物的化学结构通式如I所示:
其中,R1选自:氢、4-氟、4-氯、4-甲基;R2选自:氢、甲基;R3选自:3-甲基苯基、2,4-二氯苯基、4-氟苯基、2,2-二氟乙基、2-溴苯基、4-苯基-1-丁基、3-甲氧基苯基、环丙基、4-苯基噻唑-2-基、3-羟基-1-丙基、4-吗啉基苯基、4-氯苯乙基、3-氟苯基、2-氯-3-吡啶基、4-(4-甲基苯基)噻唑-2-基、3,5-二氯苯基、3-硝基苯基、2,4-二甲基苯基、2-氯苯乙基、2-羟基乙基、3-吡啶甲基。
本发明的酰基硫脲补骨脂素类衍生物I及其中间体的合成路线如下:
化合物I的合成路线
本发明所述酰基硫脲补骨脂素类衍生物I的合成方法分为以下步骤:
A.化合物3的制备:
取化合物1于反应瓶中,加入化合物2,随后搅拌下缓慢滴加98%浓硫酸,室温条件下进行搅拌;反应完毕后,加入适量甲醇,随后将其倒入冰水中,产生大量白色固体,抽滤、烘干得到化合物3;
B.化合物5的制备:
取化合物3于反应瓶中,加入适量无水乙腈,随后搅拌下依次加入碳酸钾、碘化钾以及化合物4,加热回流;反应完毕后,减压脱除大部分乙腈,加入水和乙酸乙酯进行萃取,有机相用饱和氯化钠溶液进行洗涤,无水硫酸钠干燥,减压抽滤,滤液浓缩除去溶剂,柱层析纯化得到化合物5;
C.化合物6的制备:
取化合物5于反应瓶中,加入适量异丙醇,搅拌下缓慢滴加1摩尔/升氢氧化钠溶液,加热回流;反应完毕后,减压脱除大部分异丙醇,用1摩尔/升盐酸溶液调节体系pH=1-2,将所产生的固体抽滤、烘干得到化合物6;
D.化合物7的制备:
取化合物6于反应瓶中,加入适量无水二氯甲烷和2-3滴N,N-二甲基甲酰胺,搅拌下缓慢滴加草酰氯的二氯甲烷溶液,室温下搅拌过夜;反应完毕后,减压脱除二氯甲烷,得到化合物7;
E.化合物8的制备:
取适量无水乙腈于反应瓶中,加入硫氰化铵,搅拌下待硫氰化铵溶解以后,缓慢滴加化合物7的乙腈溶液,室温下搅拌过夜;反应完毕后,抽滤除去不溶物,滤液浓缩除去溶剂,得到化合物8;
F.化合物I的制备:
取化合物8于反应瓶中,加入适量无水乙腈,搅拌下缓慢加入取代的胺,室温下搅拌过夜,反应完毕后,减压脱除大部分乙腈,加入水和乙酸乙酯进行萃取,有机相用饱和氯化钠溶液进行洗涤,无水硫酸钠干燥,减压抽滤,滤液浓缩除去溶剂,柱层析纯化得到化合物I。
作为一个优选实施方案,本发明的酰基硫脲补骨脂素类衍生物的合成方法分以下步骤:
A.化合物3的制备:
100毫升圆底烧瓶中加入18.2毫摩尔间苯二酚和18.2毫摩尔乙酰丁二酸二甲酯,随后搅拌下缓慢滴加2.73毫升98%浓硫酸,滴加完毕以后将反应体系在室温下搅拌过夜。TLC进行监测,反应完以后加入30毫升无水甲醇,并将其倒入冰水中,产生大量白色固体,抽滤得到的固体,粗产物用乙醚洗涤,并用乙醇-水进行重结晶,得到化合物3;化合物3制备的量和反应容器的体积按相应比例扩大或缩小。
B.化合物5的制备:
100毫升圆底烧瓶中加入4.03毫摩尔化合物3和30毫升无水乙腈,室温搅拌下依次加入4.836毫摩尔化合物4、16.12毫摩尔无水碳酸钾以及0.403毫摩尔碘化钾,随后将反应体系加热回流5小时。TLC进行监测,反应完以后静置冷却至室温,减压脱除大部分溶剂,剩余物中加入30毫升水,用乙酸乙酯萃取三遍(15毫升×3),有机相用饱和氯化钠溶液洗涤三遍(15毫升×3),合并有机层用无水硫酸钠干燥;减压抽滤,滤液浓缩除去溶剂,用石油醚/乙酸乙酯(3∶1,体积/体积)洗脱剂柱层析纯化得到化合物5;化合物5制备的量和反应容器的体积按相应比例扩大或缩小。
C.化合物6的制备:
100毫升圆底烧瓶中加入1克化合物5和30毫升异丙醇,室温搅拌下缓慢滴加30毫升1摩尔/升氢氧化钠溶液,滴加完毕将反应体系加热回流4小时。TLC进行监测,反应完以后将体系静置冷却至室温,减压脱除大部分异丙醇,剩余物中加入1摩尔/升盐酸溶液调节体系pH=1,析出大量固体,抽滤,烘干,得到化合物6;化合物6制备的量和反应容器的体积按相应比例扩大或缩小。
D.化合物7的制备:
100毫升圆底烧瓶中加入0.85毫摩尔化合物6和20毫升无水二氯甲烷,搅拌下滴加2-3滴N,N-二甲基甲酰胺,随后缓慢滴加含有3.4毫摩尔草酰氯的二氯甲烷溶液,滴加完毕将反应体系在室温下搅拌2小时。TLC进行监测,反应完以后减压脱除二氯甲烷,得到化合物7;化合物7制备的量和反应容器的体积按相应比例扩大或缩小。
E.化合物8的制备:
100毫升圆底烧瓶中加入20毫升无水乙腈和1.7毫摩尔硫氰化铵,搅拌下待硫氰化铵发生溶解以后,缓慢滴加含有0.85毫摩尔化合物7的乙腈溶液,滴加完毕将反应体系在室温下搅拌2小时。TLC进行监测,反应完以后抽滤除去不溶物,滤液浓缩除去溶剂,得到化合物8;化合物8制备的量和反应容器的体积按相应比例扩大或缩小。
F.化合物I的制备:
100毫升圆底烧瓶中加入1毫摩尔化合物8和30毫升无水乙腈,搅拌下缓慢加入1毫摩尔取代的胺,随后将反应体系在室温下搅拌过夜。TLC进行监测,反应完以后减压脱除大部分溶剂,剩余物中加入30毫升水,用乙酸乙酯萃取三遍(15毫升×3),有机相用饱和氯化钠溶液洗涤三遍(15毫升×3),合并有机层用无水硫酸钠干燥;减压抽滤,滤液浓缩除去溶剂,用石油醚/乙酸乙酯(6∶1,体积/体积)洗脱剂柱层析纯化得到化合物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。
其中,取代基R1、R2、R3定义如前所述;R1选自:氢、4-氟、4-氯、4-甲基;R2选自:氢、甲基;R3选自:3-甲基苯基、2,4-二氯苯基、4-氟苯基、2,2-二氟乙基、2-溴苯基、4-苯基-1-丁基、3-甲氧基苯基、环丙基、4-苯基噻唑-2-基、3-羟基-1-丙基、4-吗啉基苯基、4-氯苯乙基、3-氟苯基、2-氯-3-吡啶基、4-(4-甲基苯基)噻唑-2-基、3,5-二氯苯基、3-硝基苯基、2,4-二甲基苯基、2-氯苯乙基、2-羟基乙基、3-吡啶甲基。
本发明提供了所述酰基硫脲补骨脂素类衍生物I在制备杀真菌剂中的用途。
本发明提供了所述酰基硫脲补骨脂素类衍生物I在制备抗烟草花叶病毒剂中的用途。
本发明提供了所述酰基硫脲补骨脂素类衍生物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。
本发明提供了所述酰基硫脲补骨脂素类衍生物I在防治农业和林业以及园艺植物虫害中的用途。
所述酰基硫脲补骨脂素类衍生物I与农业化学品共同施用;所述农业化学品选自:杀虫剂、杀菌剂、抗植物病毒剂、杀螨剂中的一种或几种。
所述酰基硫脲补骨脂素类衍生物I与所述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、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;
酰基硫脲补骨脂素类衍生物I在所述杀虫组合物中的质量百分含量是1%-90%;优选地,所述酰基硫脲补骨脂素类衍生物I与所述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;
所述杀虫组合物防治的植物虫害选自: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。
所述酰基硫脲补骨脂素类衍生物I与所述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;
所述杀菌剂选自:苯并噻二唑、噻酰菌胺、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、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;
所述酰基硫脲补骨脂素类衍生物I在所述杀菌组合物中总的质量百分含量是1%-90%;所述酰基硫脲补骨脂素类衍生物I与所述杀菌剂的比例为质量百分比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;
所述杀菌组合物防治的植物病害选自: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。
所述酰基硫脲补骨脂素类衍生物I与所述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;
所述抗病毒药剂选自:苯并噻二唑、噻酰菌胺、异噻菌胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、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、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素、盐酸吗啉胍;
所述酰基硫脲补骨脂素类衍生物I在所述抗病毒组合物中总的质量百分含量是1%-90%;优选地,所述酰基硫脲补骨脂素类衍生物I与所述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。
所述酰基硫脲补骨脂素类衍生物I与所述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;
所述杀螨剂选自:敌敌畏、庚烯磷、速灭磷、久效磷、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、水胺硫磷、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;
所述酰基硫脲补骨脂素衍生物I在所述杀螨组合物中总的质量百分含量是1%-90%;所述酰基硫脲补骨脂素类衍生物I与所述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,所述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。
本发明所述酰基硫脲补骨脂素类衍生物I的生物活性测定如下:
F.本发明的酰基硫脲补骨脂素类衍生物I的杀菌活性测定:
本发明的酰基硫脲补骨脂素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N,N-二甲基甲酰胺中,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:AS:番茄早疫病菌,其拉丁名为:Alternaria solani、BC:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、CA:花生褐斑病菌,其拉丁名为:Cercospora arachidicola、GZ:小麦赤霉病菌,其拉丁名为:Gibberella zeae、PP:苹果轮纹病菌,其拉丁名为:Physalosporapiricola、PS:水稻纹枯病菌,其拉丁名为:Pellicularia sasakii、SS:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum。
本发明的有益效果是:对酰基硫脲补骨脂素类衍生物I进行了先导优化,并对酰基硫脲补骨脂素类衍生物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酰基硫脲补骨脂素类衍生物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3的制备:
100毫升圆底烧瓶中加入18.2毫摩尔间苯二酚和18.2毫摩尔乙酰丁二酸二甲酯,随后搅拌下缓慢滴加2.73毫升98%浓硫酸,滴加完毕以后将反应体系在室温下搅拌过夜。TLC进行监测,反应完以后加入30毫升无水甲醇,并将其倒入冰水中,产生大量白色固体,抽滤得到的固体,粗产物用乙醚洗涤,并用乙醇-水进行重结晶,得到化合物3;收率81%;核磁数据如下:1H NMR(400MHz,DMSO)δ10.50(s,1H),7.59(d,J=8.8Hz,1H),6.79(dd,J=8.7,2.1Hz,1H),6.69(d,J=2.1Hz,1H),3.61(s,2H),3.57(s,3H),2.30(s,3H)。化合物3制备的量和反应容器的体积按相应比例扩大或缩小。
实施例2:化合物5的制备:
100毫升圆底烧瓶中加入4.03毫摩尔化合物3和30毫升无水乙腈,室温搅拌下依次加入4.836毫摩尔化合物4、16.12毫摩尔无水碳酸钾以及0.403毫摩尔碘化钾,随后将反应体系加热回流5小时。TLC进行监测,反应完以后静置冷却至室温,减压脱除大部分溶剂,剩余物中加入30毫升水,用乙酸乙酯萃取三遍(15毫升×3),有机相用饱和氯化钠溶液洗涤三遍(15毫升×3),合并有机层用无水硫酸钠干燥;减压抽滤,滤液浓缩除去溶剂,用石油醚/乙酸乙酯(3∶1,体积/体积)洗脱剂柱层析纯化得到化合物5;收率62%;核磁数据如下:1HNMR(400MHz,DMSO)δ8.04(d,J=7.2Hz,2H),7.78-7.68(m,2H),7.59(t,J=7.7Hz,2H),7.11(d,J=2.5Hz,1H),7.05(dd,J=8.9,2.6Hz,1H),5.76(s,2H),3.67(s,2H),3.62(s,3H),2.39(s,3H)。化合物5制备的量和反应容器的体积按相应比例扩大或缩小。
实施例3:化合物6的制备:
100毫升圆底烧瓶中加入1克化合物5和30毫升异丙醇,室温搅拌下缓慢滴加30毫升1摩尔/升氢氧化钠溶液,滴加完毕将反应体系加热回流4小时。TLC进行监测,反应完以后将体系静置冷却至室温,减压脱除大部分异丙醇,剩余物中加入1摩尔/升盐酸溶液调节体系pH=1,析出大量固体,抽滤,烘干,得到化合物6;收率54%;核磁数据如下:1H NMR(400MHz,DMSO)δ12.54(s,1H),8.49(s,1H),8.18(s,1H),7.84(d,J=7.3Hz,2H),7.78(s,1H),7.58(t,J=7.6Hz,2H),7.48(dd,J=15.2,7.8Hz,1H),3.68(s,2H),2.55(s,3H)。
化合物6制备的量和反应容器的体积按相应比例扩大或缩小。
实施例4:化合物7的制备:
100毫升圆底烧瓶中加入0.3克化合物6和20毫升无水二氯甲烷,搅拌下滴加2滴N,N-二甲基甲酰胺,随后缓慢滴加含有0.46克草酰氯的二氯甲烷溶液,滴加完毕将反应体系在室温下搅拌2小时。TLC进行监测,反应完以后减压脱除二氯甲烷,得到化合物7;化合物7未经纯化直接用于下一步。化合物7制备的量和反应容器的体积按相应比例扩大或缩小。
实施例5:化合物8的制备:
100毫升圆底烧瓶中加入20毫升无水乙腈和0.14克硫氰化铵,搅拌下待硫氰化铵发生溶解以后,缓慢滴加含有0.32克化合物7的乙腈溶液,滴加完毕将反应体系在室温下搅拌2小时。TLC进行监测,反应完以后抽滤除去不溶物,滤液浓缩除去溶剂,得到化合物8;化合物8未经纯化直接用于下一步。化合物8制备的量和反应容器的体积按相应比例扩大或缩小。
实施例6:化合物I的制备:
100毫升圆底烧瓶中加入1毫摩尔化合物8和30毫升无水乙腈,搅拌下缓慢加入1毫摩尔取代的胺,随后将反应体系在室温下搅拌过夜。TLC进行监测,反应完以后减压脱除大部分溶剂,剩余物中加入30毫升水,用乙酸乙酯萃取三遍(15毫升×3),有机相用饱和氯化钠溶液洗涤三遍(15毫升×3),合并有机层用无水硫酸钠干燥;减压抽滤,滤液浓缩除去溶剂,用石油醚/乙酸乙酯(6∶1,体积/体积)洗脱剂柱层析纯化得到化合物I;收率:64-95%;当R1为氢,R2为氢,R3为4-氟苯基时,化合物I-1的核磁数据如下:1H NMR(400MHz,DMSO)δ12.20(s,1H),11.81(s,1H),8.48(s,1H),8.21(s,1H),7.82(d,J=6.7Hz,3H),7.60(dd,J=8.2,4.9Hz,2H),7.55(t,J=7.6Hz,2H),7.43(t,J=7.1Hz,1H),7.21(t,J=8.7Hz,2H),3.95(s,2H),2.58(s,3H)。化合物I-1制备的量和反应容器的体积按相应比例扩大或缩小;化合物I的理化和结构参数见表1。
实施例7:本发明的酰基硫脲补骨脂素类衍生物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,其拉丁名为:.Alternaria solani、B.c:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,其拉丁名为:Cercospora arachidicola、G.z:小麦赤霉病菌,其拉丁名为:Gibberella zeae、P.p:苹果轮纹病菌,其拉丁名为:Physalospora piricola、P.s:水稻纹枯病菌,其拉丁名为:Pellicularia sasakii、S.s:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorumalis,这些菌种具有很好的代表性,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。对于番茄早疫病菌,本发明的化合物DJY-3-69的抑制率为82%,高出对照药补骨脂素和YZK-C2220%以上;对于黄瓜灰霉病菌,化合物DJY-3-38、DJY-3-41、DJY-3-48、DJY-3-65、DJY-3-72、DJY-3-74的抑制率在60%以上,优于对照药补骨脂素,其中化合物DJY-3-41、DJY-3-65的抑制率在90%以上,高出对照药补骨脂素40%以上,且化合物DJY-3-41的杀菌活性最高,达100%,高出对照药YZK-C22近30%;对于小麦赤霉病菌,化合物DJY-3-69的抑制率为71%,与对照药补骨脂素和YZK-C22相当或高于对照药剂,且高出对照药补骨脂素10%;对于苹果轮纹病菌,化合物DJY-3-69的抑制率为78%,优于对照药补骨脂素和YZK-C22,且高出对照药补骨脂素30%。
实施例8:本发明的酰基硫脲补骨脂素类衍生物I在制备农药组合物中的应用:
本发明的酰基硫脲补骨脂素类衍生物I制备农药组合物,该组合物含本发明的酰基硫脲补骨脂素类衍生物I及其中间体为活性成分,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50%重量的表面活性剂。
实施例9:本发明的酰基硫脲补骨脂素类衍生物I在制备农药复配组合物中的应用:
本发明的酰基硫脲补骨脂素类衍生物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酰基硫脲补骨脂素类衍生物I及其中间体和其他商品农药,即杀虫剂、杀螨剂、杀菌剂、抗病毒剂或植物激活剂作为活性成分,本发明的酰基硫脲补骨脂素类衍生物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,以及任选0到50%重量的表面活性剂。
实施例10:本发明的酰基硫脲补骨脂素类衍生物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:
本发明的酰基硫脲补骨脂素类衍生物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、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;本发明的酰基硫脲补骨脂素类衍生物I在所述杀虫组合物中的质量百分含量是1%-90%,本发明的酰基硫脲补骨脂素类衍生物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;所述杀虫组合物防治的植物虫害选自: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11:本发明的酰基硫脲补骨脂素类衍生物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:
本发明的酰基硫脲补骨脂素类衍生物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、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、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;本发明的酰基硫脲补骨脂素类衍生物I在所述杀菌组合物中总的质量百分含量是1%-90%,本发明的酰基硫脲补骨脂素类衍生物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;所述杀菌组合物防治的植物病害选自: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12:本发明的酰基硫脲补骨脂素类衍生物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:
本发明的酰基硫脲补骨脂素类衍生物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、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、DL-β-氨基丁酸、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素、盐酸吗啉胍;本发明的酰基硫脲补骨脂素类衍生物I在所述抗病毒组合物中总的质量百分含量是1%-90%,本发明的酰基硫脲补骨脂素类衍生物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13:本发明的酰基硫脲补骨脂素类衍生物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:
本发明的酰基硫脲补骨脂素类衍生物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、久效磷、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、水胺硫磷、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;本发明的酰基硫脲补骨脂素类衍生物I在所述杀螨组合物中总的质量百分含量是1%-90%,本发明的酰基硫脲补骨脂素类衍生物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
本发明提供一类酰基硫脲补骨脂素类衍生物;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。
表2本发明的酰基硫脲补骨脂素类衍生物I的抑菌活性(50微克/毫升的抑制率/%)
序号 | 化合物 | A.s | B.c | C.a | G.z | P.p | P.s | S.s |
1 | DJY-3-33 | 13 | 29 | 26 | 33 | 7 | 21 | 9 |
2 | DJY-2-83 | 0 | 39 | 30 | 24 | 18 | 8 | 12 |
3 | DJY-3-24 | 43 | 44 | 27 | 41 | 19 | 1 | 16 |
4 | DJY-3-30 | 7 | 44 | 24 | 16 | 6 | 12 | 9 |
5 | DJY-3-39 | 18 | 37 | 30 | 19 | 10 | 8 | 10 |
6 | DJY-3-66 | 4 | 35 | 27 | 16 | 11 | 17 | 11 |
7 | DJY-3-69 | 82 | 39 | 23 | 71 | 78 | 9 | 9 |
8 | DJY-3-38 | 0 | 64 | 24 | 27 | 8 | 10 | 16 |
9 | DJY-3-41 | 33 | 100 | 33 | 40 | 33 | 52 | 16 |
10 | DJY-3-43 | 17 | 52 | 24 | 33 | 17 | 12 | 18 |
11 | DJY-3-45 | 9 | 41 | 23 | 31 | 14 | 25 | 11 |
12 | DJY-3-48 | 10 | 69 | 29 | 30 | 8 | 15 | 17 |
13 | DJY-3-52 | 12 | 49 | 27 | 33 | 19 | 19 | 19 |
14 | DJY-3-53 | 0 | 33 | 26 | 24 | 19 | 4 | 10 |
15 | DJY-3-65 | 16 | 92 | 61 | 36 | 17 | 4 | 19 |
16 | DJY-3-72 | 0 | 66 | 14 | 25 | 7 | 10 | 5 |
17 | DJY-3-70 | 9 | 33 | 24 | 33 | 12 | 9 | 6 |
18 | DJY-3-76 | 0 | 31 | 21 | 23 | 15 | 14 | 12 |
19 | DJY-3-75 | 23 | 44 | 24 | 22 | 17 | 13 | 18 |
20 | DJY-3-74 | 7 | 60 | 39 | 36 | 20 | 20 | 11 |
21 | DJY-3-71 | 13 | 49 | 31 | 33 | 0 | 33 | 13 |
22 | 补骨脂素 | 56 | 50 | 65 | 63 | 44 | 52 | 58 |
23 | YZK-C22 | 58 | 72 | 74 | 75 | 57 | 81 | 61 |
A.s:番茄早疫病菌,其拉丁名为:.Alternaria solani、B.c:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、C.a:花生褐斑病菌,其拉丁名为:Cercospora arachidicola、G.z:小麦赤霉病菌,其拉丁名为:Gibberella zeae、P.p:苹果轮纹病菌,其拉丁名为:Physalospora piricola、P.s:水稻纹枯病菌,其拉丁名为:Pellicularia sasakii、S.s:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorumalis。
Claims (7)
2.根据权利要求1所述酰基硫脲补骨脂素类衍生物I的具体合成路线和方法为:
所述取代基的定义如权利要求1所述,具体合成方法分为以下步骤:
A.化合物3的制备:
取化合物1于反应瓶中,加入化合物2,随后搅拌下缓慢滴加98%浓硫酸,室温条件下进行搅拌;反应完毕后,加入适量甲醇,随后将其倒入冰水中,产生大量白色固体,抽滤、烘干得到化合物3;
B.化合物5的制备:
取化合物3于反应瓶中,加入适量无水乙腈,随后搅拌下依次加入碳酸钾、碘化钾以及化合物4,加热回流;反应完毕后,减压脱除大部分乙腈,加入水和乙酸乙酯进行萃取,有机相用饱和氯化钠溶液进行洗涤,无水硫酸钠干燥,减压抽滤,滤液浓缩除去溶剂,柱层析纯化得到化合物5;
C.化合物6的制备:
取化合物5于反应瓶中,加入适量异丙醇,搅拌下缓慢滴加1摩尔/升氢氧化钠溶液,加热回流;反应完毕后,减压脱除大部分异丙醇,用1摩尔/升盐酸溶液调节体系pH=1-2,将所产生的固体抽滤、烘干得到化合物6;
D.化合物7的制备:
取化合物6于反应瓶中,加入适量无水二氯甲烷和2-3滴N,N-二甲基甲酰胺,搅拌下缓慢滴加草酰氯的二氯甲烷溶液,室温下搅拌过夜;反应完毕后,减压脱除二氯甲烷,得到化合物7;
E.化合物8的制备:
取适量无水乙腈于反应瓶中,加入硫氰化铵,搅拌下待硫氰化铵溶解以后,缓慢滴加化合物7的乙腈溶液,室温下搅拌过夜;反应完毕后,抽滤除去不溶物,滤液浓缩除去溶剂,得到化合物8;
F.化合物I的制备:
取化合物8于反应瓶中,加入适量无水乙腈,搅拌下缓慢加入取代的胺,室温下搅拌过夜,反应完毕后,减压脱除大部分乙腈,加入水和乙酸乙酯进行萃取,有机相用饱和氯化钠溶液进行洗涤,无水硫酸钠干燥,减压抽滤,滤液浓缩除去溶剂,柱层析纯化得到化合物I。
3.权利要求1所述的酰基硫脲补骨脂素类衍生物I在制备农用杀真菌剂中的用途。
4.一种农用杀菌组合物,其包含权利要求1所述的酰基硫脲补骨脂素类衍生物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所述的酰基硫脲补骨脂素类衍生物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,以及任选0到25%重量的表面活性剂。
5.一种农用杀菌复配组合物,其包含权利要求1所述的酰基硫脲补骨脂素类衍生物I和其他商品杀菌剂复配作为活性成分,酰基硫脲补骨脂素类衍生物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。
6.一种农用杀虫、杀螨复配组合物,其包含权利要求1所述的酰基硫脲补骨脂素类衍生物I和其他商品杀虫、杀螨剂复配作为活性成分,酰基硫脲补骨脂素类衍生物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。
7.一种抗植物病毒剂复配组合物,其包含权利要求1所述的酰基硫脲补骨脂素类衍生物I和其他商品抗植物病毒剂复配作为活性成分,酰基硫脲补骨脂素类衍生物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。
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