CN101624382B - 具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2h-1,3-苯并噁嗪 - Google Patents
具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2h-1,3-苯并噁嗪 Download PDFInfo
- Publication number
- CN101624382B CN101624382B CN2009100440744A CN200910044074A CN101624382B CN 101624382 B CN101624382 B CN 101624382B CN 2009100440744 A CN2009100440744 A CN 2009100440744A CN 200910044074 A CN200910044074 A CN 200910044074A CN 101624382 B CN101624382 B CN 101624382B
- Authority
- CN
- China
- Prior art keywords
- dihydro
- nitrophenyl
- benzoxazines
- phenyl
- tolyl
- 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.)
- Expired - Fee Related
Links
- LPXKJTDGMVTOQU-UHFFFAOYSA-N COc(cc1)ccc1N(C1)C(c(cc2)ccc2[N+]([O-])=O)Oc2c1cccc2 Chemical compound COc(cc1)ccc1N(C1)C(c(cc2)ccc2[N+]([O-])=O)Oc2c1cccc2 LPXKJTDGMVTOQU-UHFFFAOYSA-N 0.000 description 1
- 0 Nc1ccc(*(C2)C(c(cc3)ccc3[N+]([O-])=O)Oc3c2cccc3)cc1 Chemical compound Nc1ccc(*(C2)C(c(cc3)ccc3[N+]([O-])=O)Oc3c2cccc3)cc1 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
本发明公开了一种具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪,式(I)是其结构式,式中,苯环A上有取代基R1、R2、R3,苯环B上有取代基R4、R5、R6,及二氢噁嗪环上有取代基R7。取代基R1是-H或-CH3时:R2、R3是-H,R4、R5、R6中任一个是-NO2,其余是-H,R7是-H或是-CH3或是-C6H5;取代基R2是-CH3时:R1、R3是-H,R4、R5、R6中任一个是-NO2,其余是-H,R7是-H或是-CH3或是-C6H5;取代基R3是-CH3或-Cl或-OCH3时:R1、R2是-H,R4、R5、R6中任一个是-NO2,其余是-H,R7是-H或是-CH3或是-C6H5。
Description
技术领域
本发明属于农药领域,具体涉及一种具有杀虫及杀菌活性的2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪。
背景技术
3,4-二氢-2H-1,3-苯并噁嗪具有广泛的生物活性,包括杀菌,抗肿瘤和抗癌活性等。早在1951年,Urbanski报道了一类含硝基的3,4-二氢-2H-1,3-苯并噁嗪化合物,发现该类化合物具有明显的抗结核活性,而后该作者在1956年又报道了三种3,4-二氢-2H-1,3-苯并噁嗪化合物,发现此三种化合物能明显抑制小白鼠Crocker肿瘤细胞的生长(肿瘤大小较对照减小37.9%~68.4%)。1962年,Kuehne等连续报道合成了一百多种3,4-二氢-2H-1,3-苯并噁嗪类化合物,并测试了其抗小白鼠Crocker肿瘤与腺癌E0771的活性。结果显示在供试的3,4-二氢-2H-1,3-苯并噁嗪类化合物中,大部分化合物对小白鼠Crocker肿瘤与腺癌E0771具有抑制活性。随后,等报道了3,4-二氢-2H-1,3-苯并噁嗪类化合物对埃利希氏腹水癌细胞和异戊巴比妥腹水癌细胞的抑制活性。结果表明在48个供试的3,4-二氢-2H-1,3-苯并噁嗪类化合物中,除3个化合物无活性外,其他45个化合物均具有抑制活性,并且其中6个3,4-二氢-2H-1,3-苯并噁嗪类化合物对上述两种癌细胞均表现出很强的抑制作用。1980年,Mireya等报道了单3,4-二氢-2H-1,3-苯并噁嗪与双3,4-二氢-2H-1,3-苯并噁嗪类化合物均能明显地抑制埃希氏大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌、铜绿假单胞菌的生长。其中双3,4-二氢-2H-1,3-苯并噁嗪的杀菌活性优于单3,4-二氢-2H-1,3-苯并噁嗪噁嗪,甚至双3,4-二氢-2H-1,3-苯并噁嗪抗革兰氏阳性菌的活性优于几种常见的抗生素,如氨比西林,四环素和氯霉素等。
但是,我们发现文献中研究得最多的是3-取代3,4-二氢-2H-1,3-苯并噁嗪类化合物的合成以及它们在医用方面的杀菌、抗肿瘤和抗癌活性等,而2,3-二取代-3,4-二氢-2H-1,3-苯并噁嗪类化合物的合成及其在农用方面的杀虫、杀菌等生物活性的研究报道较少。
发明内容
本发明的目的在于提供一种不同以往的具有杀虫及杀菌活性的2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪类农药。
本发明所提供的2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪,其结构式为:
式中,苯环A上有取代基R1、R2、R3,苯环B上有取代基R4、R5、R6,及二氢噁嗪环上有取代基R7;
式中,取代基R1是-H时:R2是-H,R3是-H,R4是-NO2,R5是-H,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R2是-H,R3是-H,R4是-H,R5是-NO2,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R2是-H,R3是-H,R4是-H,R5是-H,R6是-NO2,R7是-H或是-CH3或是-C6H5;
式中,取代基R1是-CH3时:R2是-H,R3是-H,R4是-NO2,R5是-H,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R2是-H,R3是-H,R4是-H,R5是-NO2,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R2是-H,R3是-H,R4是-H,R5是-H,R6是-NO2,R7是-H或是-CH3或是-C6H5;
式中,取代基R2是-CH3时:R1是-H,R3是-H,R4是-NO2,R5是-H,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R3是-H,R4是-H,R5是-NO2,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R3是-H,R4是-H,R5是-H,R6是-NO2,R7是-H或是-CH3或是-C6H5;
式中,取代基R3是-CH3时:R1是-H,R2是-H,R4是-NO2,R5是-H,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R2是-H,R4是-H,R5是-NO2,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R2是-H,R4是-H,R5是-H,R6是-NO2,R7是-H或是-CH3或是-C6H5;
式中,取代基R3是-Cl时:R1是-H,R2是-H,R4是-NO2,R5是-H,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R2是-H,R4是-H,R5是-NO2,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R2是-H,R4是-H,R5是-H,R6是-NO2,R7是-H或是-CH3或是-C6H5;
式中,取代基R3是-OCH3时:R1是-H,R2是-H,R4是-NO2,R5是-H,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R2是-H,R4是-H,R5是-NO2,R6是-H,R7是-H或是-CH3或是-C6H5;或者,R1是-H,R2是-H,R4是-H,R5是-H,R6是-NO2,R7是-H或是-CH3或是-C6H5。
本发明所提供的具有杀虫及杀菌活性的2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪,包括:2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪。
2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
具体实施方式
下面结合实例来说明2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪的杀虫及杀菌活性。
采用国家农药创制工程技术研究中心生物活性测定标准操作程序(SOP)对2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪进行了杀虫活性测试。以蚜虫(Aphis fabae)为供试材料,采用浸渍法,筛选化合物浓度为500mg/L,48h后检查和记载死亡虫数,杀虫活性用致死百分率表示,测试结果见表一。
表一 16种化合物对蚜虫的杀虫活性
化合物 | 蚜虫/% |
2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 48.01 |
2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 59.42 |
2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 58.87 |
2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 24.86 |
2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 51.05 |
2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 60.00 |
2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 31.81 |
2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 40.41 |
2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 20.83 |
3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 35.04 |
3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 31.11 |
3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 51.46 |
3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 59.58 |
3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁 | 38.25 |
嗪 | |
2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 80.00 |
2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 51.35 |
从表一可以看出,16种2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪化合物对蚜虫均表现出较强的杀虫活性,其中,2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪化合物杀蚜虫活性达到了80%,其它化合物的杀虫活性处于24.86%~60.00%之间。
同样采用SOP标准操作程序对2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪进行了杀菌活性测试。以小麦赤霉病菌(Gibberella zeae),辣椒疫霉病菌(phytophythora capsici),烟草赤星病菌(Alternaria alternata),黄瓜灰霉病菌(Botrytis cinerea),稻纹枯病菌(Rhizoctonia solani),油菜菌核病菌(Sclerotonia sclerotiorum)为供试材料。当供试材料为小麦赤霉病菌、辣椒疫霉病菌、烟草赤星病菌、黄瓜灰霉病菌和油菜菌核病菌时:采用含毒培养基法,普筛浓度为25mg/L;稻纹枯病菌:采用离体叶片培养法,普筛浓度为500mg/L。前五者的杀菌活性用抑制百分率表示,稻纹枯病菌的杀菌活性用防效百分率表示。测试结果见表二。
表二 16种化合物对蚜虫的杀菌活性
化合物 | 赤霉病菌/% | 疫霉病菌/% | 赤星病菌/% | 灰霉病菌/% | 纹枯病菌/% | 菌核病菌/% |
2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 10.3 | 37.4 | 17.5 | 13.6 | 50.0 | 0 |
2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 30.9 | 28.0 | 10.5 | 19.0 | 100 | 59.8 |
2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 30.9 | 28.0 | 0 | 13.6 | 0 | 0 |
2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 39.2 | 33.6 | 14.0 | 6.8 | 50.5 | 56.1 |
2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 30.9 | 9.3 | 35.1 | 27.2 | 80.0 | 0 |
2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 30.9 | 37.4 | 10.5 | 20.4 | 0 | 0 |
2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 20.6 | 28.0 | 14.0 | 33.3 | 80.0 | 0 |
2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 20.6 | 28.0 | 10.5 | 33.3 | 0 | 0 |
2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 20.6 | 28.0 | 7.0 | 27.2 | 60.0 | 0 |
3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 30.9 | 31.8 | 42.1 | 47.6 | 0 | 74.8 |
3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 41.2 | 37.4 | 38.6 | 47.6 | 10.0 | 28.0 |
3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 51.5 | 37.4 | 45.6 | 27.2 | 80.0 | 56.1 |
3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 10.3 | 18.6 | 0 | 13.6 | 0 | 0 |
3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 14.4 | 18.6 | 10.5 | 6.8 | 0 | 0 |
2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 30.9 | 31.8 | 17.5 | 23.1 | 50.0 | 0 |
2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪 | 24.7 | 22.4 | 3.5 | 13.6 | 70.0 | 0 |
从表二可以看出,16种2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪化合物均表现出较强的杀菌活性。其中,杀稻纹枯病菌和油菜菌核病菌的活性高于杀小麦赤霉病菌、辣椒疫霉病菌、烟草赤星病菌和黄瓜灰霉病菌的活性。2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪和3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪杀稻纹枯病菌的活性均达到了80%;2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪杀稻纹枯病菌的活性甚至达到了100%。
为了更好的理解本发明,现给出制备2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪化合物的实例,本发明包括但不限于此制备方法。
实例1:SnCl4催化合成2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪。
将2-((对甲苯基氨基)甲基)苯酚(1.07g,5mmol)与间硝基苯甲醛(0.98g,6.5mmol,1.3eq)溶于三氯甲烷与环己烷的混合溶液中,加入含有四氯化锡(0.26g,20mol%)的三氯甲烷溶液,安装分水器,加热回流5h(TLC检测),反应完后,用三乙胺将体系的pH值调到8,然后加入100mL乙酸乙酯溶液,分别用水(100mL×2次)与氯化钠的饱和溶液(100mL×2次)洗有机相,有机相用无水硫酸钠干燥,减压脱溶得黄色油状物。油状物用乙酸乙酯-石油醚重结晶得1.64g黄色固体产物,产率94.7%,熔点(mp):123.6-125.5℃。该化合物的1H NMR、13C NMR和IR数据如下:
1H MR(CDCl3,500MHz)δ:2.27(s,3H,CH3),4.25(d,J=17.0Hz,1H,CH2),4.35(d,J=17.0Hz,1H,CH2),6.56(s,1H,CH),6.86(d,J=8.0Hz,2H),7.02~7.03(m,1H),7.07~7.12(m,4H),7.16(d,J=2.5Hz,1H),7.51(t,J=8.0Hz,1H),7.90(d,J=8.5Hz,1H),8.15~8.17(m,1H),8.45(s,1H)。13C NMR(CDCl3,125MHz)δ:20.68,47.20,87.61,117.09,120.14,121.01(2C),121.16,122.29,123.23,126.67,128.37,129.69,129.91(2C),132.58,133.09,141.64,146.95,148.70,152.39。IR(KBr):3093,3070,3022,2978,2857,1611,1583,1528,1513,1490,1457,1380,1346,1272,1265,1227,1197,1149,1127,1108,1083,1033,995,956,941,923,893,821,811,805,752,734,711,694,670,594,524,501,483cm-1。
如下化合物的制备方法同实例1。
2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲苯基氨基)甲基)苯酚,邻硝基苯甲醛为原料。产率79.7%,黄色固体,熔点(mp):152.6-153.0℃。1H NMR(CDCl3,500MHz)δ:2.25(s,3H,CH3),4.00(d,J=17.0Hz,1H,CH2),4.19(d,J=17.0Hz,1H,CH2),6.85(s,1H,CH),6.86~6.88(m,1H),7.00~7.06(m,6H),7.17~7.20(m,1H),7.44~7.47(m,2H),7.61~7.63(m,1H),7.72~7.74(m,1H)。13C NMR(CDCl3,125MHz)δ:20.74,47.12,85.52,116.72,120.45,120.86(2C),121.13,124.45,126.72,128.41,128.76,129.21,129.80(2C),131.84,132.76,132.99,146.74,149.08,152.60。IR(KBr):3083,3021,2972,2920,1610,1585,1530,1513,1486,1456,1437,1386,1363,1337,1292,1276,1268,1224,1198,1144,1109,1034,1024,1015,978,961,935,852,839,820,782,757,736,714,687,679,632,589,559,529,470cm-1。
2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲苯基氨基)甲基)苯酚,对硝基苯甲醛为原料。产率64.3%,黄色固体,熔点(mp):93.7-96.9℃。1H NMR(CDCl3,500MHz)δ:2.27(s,3H,CH3),4.22(d,J=17.0Hz,1H,CH2),4.34(d,J=16.5Hz,1H,CH2),6.57(s,1H,CH),6.86~6.88(m,2H),6.99(d,J=3.5Hz,1H),7.06~7.10(m,4H),7.16~7.19(m,1H),7.74(d,J=8.5Hz,2H),8.18~8.21(m,2H)。13CNMR(CDCl3,125MHz)δ:20.64,47.13,87.72,116.94,120.10,120.73(3C),121.14,123.83,123.99,126.67,127.92,128.29,129.87(2C),132.44,146.41,145.85,147.69,152.38。IR(KBr):2920,2859,1614,1583,1516,1490,1455,1442,1386,1343,1318,13002,1224,1205,1144,1109,1033,1014,976,960,940,905,854,829,812,760,739,712,696,589,556,527,494cm-1。
2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((间甲苯基氨基)甲基)苯酚,邻硝基苯甲醛为原料。产率69.4%,黄色固体,熔点(mp):138.1-139.0℃。1H NMR(CDCl3,500MHz)δ:2.30(s,3H,CH3),4.01(d,J=17.0Hz,1H,CH2),4.23(dd,J1=1.0Hz,J2=1.0Hz,1H,CH2),6.80(d,J=7.5Hz,1H),6.85~6.87(m,2H),6.94~6.97(m,2H),7.00(d,J=8.0Hz,1H),7.08(s,1H,CH),7.11(t,J=8.0Hz,1H),7.17~7.20(m,1H),7.43~7.48(m,2H),7.61~7.62(m,1H),7.73~7.74(m,1H)。13C NMR(CDCl3,125MHz)δ:21.72,46.79,85.03,116.76,117.27,120.41,121.05(2C),121.13,123.91,124.47,126.66,128.41,128.78,129.02,129.22,131.83,132.99,139.02,149.10,152.44。IR(KBr):3072,2947,2906,2862,1606,1586,1535,1489,1456,1445,1378,1340,1301,1273,1236,1216,1199,1169,1140,1109,1036,983,958,937,852,837,782,772,756,737,690,634,597,575,547,526,497cm-1。
2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((间甲苯基氨基)甲基)苯酚,间硝基苯甲醛为原料。产率67.7%,黄色固体,熔点(mp):101.3-102.0℃。1H NMR(CDCl3,500MHz)δ:2.32(s,3H,CH3),4.26(d,J=17.0Hz,1H,CH2),4.37(d,J=17.0Hz,1H,CH2),6.63(s,1H,CH),6.82~6.89(m,3H),7.00~7.04(m,3H),7.15~7.19(m,2H),7.51(t,J=8.0Hz,1H),7.89~7.91(m,1H),8.15~8.17(m.1H),8.44(s,1H)。13C NMR(CDCl3,125MHz)δ:21.65,46.56,86.98,117.11,117.24,120.05,121.07,121.13,122.20,123.22,123.54,126.60,128.35,129.17,129.72,133.04,139.24,141.60,148.64,149.36,152.15。IR(KBr):3092,3025,2979,2918,1602,1585,1529,1488,1475,1380,1348,1314,1271,1238,1219,1181,1123,1113,1087,1046,1032,994,958,970,942,899,891,806,776,753,735,696,688,671,599,499cm-1。
2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((间甲苯基氨基)甲基)苯酚,对硝基苯甲醛为原料。产率68.7%,黄色固体,熔点(mp):126.2-126.9℃。1H NMR(CDCl3,500MHz)δ:2.32(s,3H,CH3),4.24(d,J=16.0Hz,1H,CH2),4.38(d,J=17.0Hz,1H,CH2),6.65(s,1H,CH),6.83(t,J=7.5Hz,1H),6.85(t,J=5.0Hz,2H),7.00(dd,J1==7.0Hz,J2=3.5Hz,3H),7.16~7.20(m,2H),7.74(d,J=8.5Hz,2H),8.19(d,J=8.0Hz,2H)。13C NMR(CDCl3,125MHz)δ:21.69,46.66,87.22,117.07,117.12,120.16,120.92,121.21,123.53(2C),123.91,126.69,127.95(2C),128.36,129.25,139.31,146.51,147.81,149.36,152.32。IR(KBr):3042,1607,1584,1554,1541,1512,1489,1456,1378,1350,1306,1239,1221,1189,1169,1128,1110,1038,981,956,857,826,783,767,752,739,694,609,505cm-1。
2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((邻甲苯基氨基)甲基)苯酚,邻硝基苯甲醛为原料。产率62.7%,黄色固体,熔点(mp):164.3-165.3℃。1H NMR(CDCl3,500MHz)δ:2.20(s,3H,CH3),3.93(s,2H,CH2),6.76(d,J=12.0Hz,1H),6.83~6.86(m,1H),6.98(s,1H,CH),6.99~7.01(dd,1H,J1=7.4Hz,J2=0.9Hz),7.03(t,J=8.0Hz,1H),7.09(d,J=8.0Hz,1H),7.14(d,J=7.0Hz,1H),7.20~7.23(m,1H),7.43~7.51(m,3H),7.72(d,J=7.5Hz,1H),7.78(dd,J1=1.5Hz,J2=1.0Hz,1H)。13C NMR(CDCl3,125MHz)δ:17.93,47.84,85.79,116.61,119.57,121.08,122.95,124.92(2C),126.64,127.06,128.47,128.77,129.13,131.19,132.11,133.17,133.37,148.11,148.79,152.44。IR(KBr):3079,3025,2948,2913,1608,1597,1588,1527,1458,1439,1365,1338,1300,1274,1228,1207,1187,1142,1118,1057,1035,1021,977,955,937,855,841,827,780,760,737,725,714,684,663,634,592,564,538,487,459cm-1。
2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((邻甲苯基氨基)甲基)苯酚,间硝基苯甲醛为原料。产率65.2%,黄色固体,熔点(mp):85.0-86.1℃。1H NMR(CDCl3,500MHz)δ:2.51(s,3H,CH3),4.14(d,J=17.0Hz,1H,CH2),4.25(d,J=17.0Hz,1H,CH2),6.34(s,1H,CH),6.86~6.92(m,2H),7.05~7.13(m,3H),7.20~7.25(m,2H),7.36(d,J=7.5Hz,1H),7.53(t,J=8.0Hz,1H),7.99(d,J=2.5Hz,1H),8.16~8.18(m,1H),8.54~8.55(m,1H)。13C NMR(CDCl3,125MHz)δ:18.59,47.37,87.92,117.08,119.86,121.15,122.35,123.10,123.31,125.03,126.69,126.86,128.23,129.57,131.07,133.13,133.17,141.43,148.11,148.52,152.28。IR(KBr):2933,2885,1598,1585,1533,1490,1456,1434,1386,1380,1349,1336,1227,1215,1188,1149,1082,1033,986,959,893,807,764,755,742 724,695,673,588,530cm-1。
2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((邻甲苯基氨基)甲基)苯酚,对硝基苯甲醛为原料。产率64.3%,黄色固体,熔点(mp):128.5-129.8℃。1H NMR(CDCl3,500MHz)δ:2.50(s,3H,CH3),4.12(d,J=16.5Hz,1H,CH2),4.23(d,J=17.0Hz,1H,CH2),6.35(s,1H,CH),6.86~6.92(m,2H),7.05~7.11(m,3H),7.22~7.26(m,2H),7.36~7.38(m,1H),7.84(d,J=8.5Hz,2H),8.22~8.23(m,2H)。13C NMR(CDCl3,125MHz)δ:18.59,47.40,88.16,116.97,119.89,121.17,123.19,123.75,124.25,125.02,126.73,126.88,128.03,128.21,130.44,131.08,133.04,146.32,147.61,148.18,152.35。IR(KBr):3074,2955,2886,1607,1584,1520,1486,1456,1380,1345,1333,1228,1214,1183,1140,1106,1033,1019,1011,975,953,932,858,837,763,752,742,723,709,601,501cm-1。
2-(2-硝基苯基)-3-(4-氯苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的合成。以2-((对氯苯基氨基)甲基)苯酚,邻硝基苯甲醛为原料。产率69.3%。黄色固体,熔点(mp):140.7-141.3℃。1H NMR(CDCl3,500MHz)δ:3.99(d,J=17.0Hz,1H,CH2),4.22(d,J=17.0Hz,1H,CH2),6.85~6.90(m,2H),7.00(d,J=9.5Hz,2H),7.06~7.09(m,2H),7.17~7.22(m,3H),7.44~7.49(m,2H),7.59~7.62(m,1H),7.73~7.77(m,1H)。13CNMR(CDCl3,125MHz)δ:46.95,85.09,116.67,119.81,121.28,121.98(2C),124.49,126.60,128.25,128.57,128.61,129.14(2C),129.33,131.94,132.40,147.54,148.77,152.28。IR(KBr):2307,1609,1592,1522,1494,1457,1384,1361,1342,1304,1276,1224,1203,1113,1098,1034,1020,1008,980,949,936,855,826,782 750,740,727,645,596cm-1。
2-(4-硝基苯基)-3-(4-氯苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对氯苯基氨基)甲基)苯酚,对硝基苯甲醛为原料。产率59.4%,黄绿色固体,熔点(mp):135.9-137.6℃。1H NMR(CDCl3,500MHz)δ:4.24(d,J=17.0Hz,1H,CH2),4.34(d,J=17.0Hz,1H,CH2),6.56(s,1H,CH),6.89~6.94(m,2H),7.00(d,J=8.0Hz,1H),7.11~7.12(m,2H),7.17~7.19(m,1H),7.20~7.24(m,2H),7.72~7.74(m,2H),8.19~8.21(m,2H)。13C NMR(CDCl3,125MHz)δ:47.24,87.23,117.02,119.61,121.39,121.90(3C),123.90(2C),126.66,127.84,127.90(2C),128.53,129.29(2C),145.83,147.78,152.12。IR(KBr):3103,3075,3057,3009,2938,2973,2891,2851,1605,1593,1583,1516,1496,1487,1455,1373,1348,1331,1288,1224,1199,1182,1131,1112,1034,1005,963,930,902,855,830,819,800,753,743,724,711,642,624,602,559,536,520,472cm-1。
2-(2-硝基苯基)-3-(4-甲氧基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲氧基苯基氨基)甲基)苯酚,邻硝基苯甲醛为原料。产率72.8%,黄色固体,熔点(mp):165.9-166.9℃。1H NMR(CDCl3,500MHz)δ:3.75(s,3H,OCH3),4.01(d,J=17.0Hz,1H,CH2),4.17(d,J=17.0Hz,1H,CH2),6.77~6.79(m,2H),6.87~6.92(m,2H),6.94(s,1H,CH),7.04(d,J=8.0Hz,1H),7.09~7.11(m,2H),7.21~7.25(m,1H),7.46~7.48(m,2H),7.64~7.66(m,1H),7.75~7.76(m,1H)。13C NMR(CDCl3,125MHz)δ:47.48,55.29,85.96,114.17(2C),116.59,120.41,121.06,123.18(2C),124.28,126.64,128.27,128.59,129.06,131.75,132.77,142.48,148.95,152.63,155.92。IR(KBr):3076,2968,1607,1579,1531,1509,1488,1456,1388,1364,1299,1270,1242,1225,1199,1145,1108,1034,1022,975,960,854,830,783,758,737,685,631,589,564,551cm-1。
2-(3-硝基苯基)-3-(4-甲氧苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲氧基苯基氨基)甲基)苯酚,间硝基苯甲醛为原料。产率70.1%,黄色固体,熔点(mp):103.2-106.1℃。1H NMR(CDCl3,500MHz)δ:3.77(s,3H,OCH3),4.26(d,J=17.0Hz,1H,CH2),4.34(d,J=17.0Hz,1H,CH2),6.48(s,1H,CH),6.81~6.83(m,2H),6.90~6.91(m,2H),7.05(d,J=8.0Hz,1H),7.16~7.18(m,2H),7.20~7.23(m,1H),7.53(t,J=8.0Hz,1H),7.94(d,J=8.0Hz,1H),8.17~8.19(m,1H),8.49(s,1H)。13CNMR(CDCl3,125MHz)δ:47.99,55.36,88.17,114.31(2C),116.96,120.10,121.10,122.22,123.12,123.34(2C),126.60,128.25,129.54,133.07,141.41,142.61,148.50,152.44,155.77。IR(KBr):3070,3093,2950,2832,1610,1582,1528,1512,1488,1456,1345,1252,1227,1197,1179,1127,1085,1038,994,957,893,826,783,757,735,712,694,670,592,568,510cm-1。
2-(4-硝基苯基)-3-(4-甲氧基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲氧基苯基氨基)甲基)苯酚,对硝基苯甲醛为原料。产率75.6%,黄色固体,熔点(mp):84.3-86.1℃。1H NMR(CDCl3,500MHz)δ:3.74(s,3H,OCH3),4.21(d,J=17.0Hz,1H,CH2),4.31(d,J=17.0Hz,1H,CH2),6.46(s,1H,CH),6.77~6.80(m,2H),6.86~6.88(m,2H),7.00(d,J=8.0Hz,1H),7.11~7.14(m,2H),7.17~7.20(m,1H),7.75(d,J=8.5Hz,2H),8.18~8.19(m,2H)。13C NMR(CDCl3,125MHz)δ:48.05,55.41,88.42,114.35(2C),116.91,120.17,121.17,123.20(2C),123.76(2C),126.68,127.97(2C),128.27,142.63,146.30,147.66,152.56,155.76。IR(KBr):3014,2968,2945,2937,2908,2836,2860,1607,1583,1512,1487,1466,1457,1438,1380,1319,1300,1266,1245,1226,1201,1188,1138,1107,1037,1024,1012,974,965,950,939,855,834,822,767,739,713,695,590,560,536,504cm-1。
2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲氧基苯基氨基)甲基)苯酚,邻硝基苯甲醛为原料。产率65.7%,黄色固体,熔点(mp):130.9-131.7℃。1H NMR(CDCl3,500MHz)δ:4.04(d,J=17Hz,1H,CH2),4.26(d,J=17Hz,1H,CH2),6.89~6.92(m,2H),6.96~7.03(m,2H),7.11(s,1H,CH),7.16~7.18(m,2H),7.25~7.28(m,2H),7.46~7.49(m,2H),7.63~7.65(m,1H),7.75~7.77(m,1H)。13C NMR(CDCl3,125MHz)δ:46.78,85.24,116.75,120.36,120.55(3C),121.20,123.12,124.50,126.69,128.47,128.79,129.26(3C),131.88,132.87,149.08,152.50。IR(KBr):3023,1598,1585,1535,1496,1486,1455,1396,1365,1273,1223,1136,1110,1036,981,957,853,783,756,735,717,694,591,551,526cm-1。
2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪:2-((对甲氧基苯基氨基)甲基)苯酚,间硝基苯甲醛为原料。产率60.2%,黄色固体,熔点(mp):90.3-91.8℃。1H NMR(CDCl3,500MHz)δ:4.04(d,J=17Hz,1H,CH2),4.26(d,J=17Hz,1H,CH2),6.62(s,1H,CH),6.82~6.92(m,3H),7.02~7.06(m,3H),7.16~7.20(m,2H),7.25~7.28(m,1H),7.51~7.55(m,2H),7.66~7.76(m,2H)。13C NMR(CDCl3,125MHz)δ:47.02,87.23,116.90,120.45,120.62(3C),121.41,123.22,125.00,126.73,128.51,129.02,129.28(3C),132.11,132.90,149.09,152.78。IR(KBr):3030,2962,1605,1502,1488,1456,1398,1364,1252,1227,1138,1127,1085,994,957,893,783,757,735,713,694,592,568,510cm-1。
Claims (1)
1.一种具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2H-1,3-苯并噁嗪,选自:2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪,2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪;
2-(3-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(4-硝基苯基)-3-对甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(3-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(4-硝基苯基)-3-间甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(3-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(4-硝基苯基)-3-邻甲苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-氯苯基)-2-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-氯苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-甲氧基苯基)-3-(2-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-甲氧基苯基)-3-(3-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
3-(4-甲氧基苯基)-3-(4-硝基苯基)-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(2-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
2-(3-硝基苯基)-3-苯基-3,4-二氢-2H-1,3[e]-苯并噁嗪的结构式为:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100440744A CN101624382B (zh) | 2009-08-08 | 2009-08-08 | 具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2h-1,3-苯并噁嗪 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100440744A CN101624382B (zh) | 2009-08-08 | 2009-08-08 | 具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2h-1,3-苯并噁嗪 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101624382A CN101624382A (zh) | 2010-01-13 |
CN101624382B true CN101624382B (zh) | 2011-04-27 |
Family
ID=41520395
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009100440744A Expired - Fee Related CN101624382B (zh) | 2009-08-08 | 2009-08-08 | 具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2h-1,3-苯并噁嗪 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101624382B (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101928256B (zh) * | 2010-08-31 | 2012-05-30 | 湖南科技大学 | 具杀菌活性的3-烃基-2-芳基-1,3-苯并噁嗪 |
CN102408421B (zh) * | 2011-08-28 | 2014-07-02 | 湖南科技大学 | 具有杀菌活性的3-(1,3,4-噻二唑基)-1,3-苯并恶嗪类化合物 |
CN102408390B (zh) * | 2011-12-11 | 2013-08-07 | 湖南科技大学 | 具有杀菌活性的n-取代-3,4-二氢-1,4-苯并恶嗪类化合物 |
CN105418531B (zh) * | 2015-12-17 | 2018-11-06 | 湖南科技大学 | 2-芳基-3-酰胺基-1,3-苯并恶嗪类化合物及其制备和用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0469686A1 (en) * | 1990-07-31 | 1992-02-05 | Shell Internationale Researchmaatschappij B.V. | Pesticidal heterocyclic compounds |
CN1970535A (zh) * | 2006-12-01 | 2007-05-30 | 中国科学院上海有机化学研究所 | 乙氰菊酯的光活异构体、制备方法及其用途 |
-
2009
- 2009-08-08 CN CN2009100440744A patent/CN101624382B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0469686A1 (en) * | 1990-07-31 | 1992-02-05 | Shell Internationale Researchmaatschappij B.V. | Pesticidal heterocyclic compounds |
CN1970535A (zh) * | 2006-12-01 | 2007-05-30 | 中国科学院上海有机化学研究所 | 乙氰菊酯的光活异构体、制备方法及其用途 |
Also Published As
Publication number | Publication date |
---|---|
CN101624382A (zh) | 2010-01-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Bikobo et al. | Synthesis of 2-phenylamino-thiazole derivatives as antimicrobial agents | |
Liaras et al. | Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation | |
CN101624382B (zh) | 具杀虫杀菌活性的2,3-二芳基取代-3,4-二氢-2h-1,3-苯并噁嗪 | |
Patel et al. | Antimycobacterial and antimicrobial study of new 1, 2, 4‐triazoles with benzothiazoles | |
Yousif et al. | Synthesis and antimicrobial screening of tetra Schiff bases of 1, 2, 4, 5-tetra (5-amino-1, 3, 4-thiadiazole-2-yl) benzene | |
Bagul et al. | Design, synthesis and biological activities of novel 5-isopropyl-2-methylphenolhydrazide-based sulfonamide derivatives | |
Musa et al. | Synthesis and antimicrobial activity of N, N'-bis (2-hydroxylbenzyl)-1, 2-ethanediamine derivatives | |
CN106397422A (zh) | 含手性噁唑啉的烟酰胺类化合物及作为农用杀菌剂的用途 | |
Cunha et al. | Synthesis and antibacterial evaluation of 3, 5-diaryl-1, 2, 4-oxadiazole derivatives | |
Özkan et al. | Synthesis and antimicrobial and antioxidant activities of sulfonamide derivatives containing tetrazole and oxadiazole rings | |
CN101928256B (zh) | 具杀菌活性的3-烃基-2-芳基-1,3-苯并噁嗪 | |
CN102850342B (zh) | 一种含噻二唑的噁二唑类化合物及其制备与应用 | |
Li et al. | Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether | |
Liu et al. | Synthesis and Fungicidal Activity of Novel 2‐Heteroatomthiazole‐based Carboxanilides | |
Belakhov et al. | The application of aryl substituted derivatives of xylose as environmentally friendly multipurpose pesticides | |
Kinali-Demirci et al. | Synthesis of some novel purine derivatives incorporating tetrazole ring and investigation of their antimicrobial activity and DNA interactions | |
Dhiman et al. | Synthesis and biological evaluation of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives | |
Božinović et al. | Synthesis and anti‐Candida activity of novel benzothiepino [3, 2‐c] pyridine derivatives | |
CN107188858A (zh) | 吩嗪‑1‑甲酰哌嗪类化合物及其应用 | |
CN109251186B (zh) | 一种含苯并噻唑的查尔酮类衍生物、其制备方法及应用 | |
Ashok et al. | Synthesis of pyrazolylfuro [2, 3-f] chromenes and evaluation of their antimicrobial activity | |
Babu et al. | Synthesis of novel N-aryl-4-[6-(2-fluoropyridin-3-yl) quinazolin-2-yl]-piperazine-1-carboxamide or-carbothioamide derivatives and their antimicrobial activity | |
Khan et al. | Design and synthesis of novel triazolyl benzoxazine derivatives and evaluation of their antiproliferative and antibacterial activity | |
CN109020916A (zh) | 一种取代苯并噻唑c2烷基化衍生物及其应用 | |
CN102827094A (zh) | 2,3,6(8)-三取代-3,4-二氢-2h-1,3-苯并恶嗪类化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C17 | Cessation of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20110427 Termination date: 20130808 |