CN103524422A - 苯并咪唑衍生物及其制备方法和用途 - Google Patents
苯并咪唑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 13
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims abstract 17
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims abstract description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000012044 organic layer Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 21
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 18
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 17
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- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
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- ILBDDFPSCLDHEF-UHFFFAOYSA-N CC(C)(C1C=C(Cl)Cl)C1C(C)=O Chemical compound CC(C)(C1C=C(Cl)Cl)C1C(C)=O ILBDDFPSCLDHEF-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)([C@@]1C=C(C(F)(F)F)Cl)C1*(C)=O Chemical compound CC(C)([C@@]1C=C(C(F)(F)F)Cl)C1*(C)=O 0.000 description 1
- JCKLYLNJESKQRY-UHFFFAOYSA-N CC(C)C(C(C)=O)c(cc1)ccc1Cl Chemical compound CC(C)C(C(C)=O)c(cc1)ccc1Cl JCKLYLNJESKQRY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种苯并咪唑衍生物及其制备方法和用途，其结构式如下：
其中，R1选自H、F、Cl、Br、CH3、NO3中的一种，-OR2取代的位置为邻位、间位和对位中的一种。该苯并咪唑衍生物可以用于防治线虫，主要防治植物寄生线虫，如根结线虫，南方根结线虫（M.incognita）、爪哇根结线虫(M.javanica)、花生根结线虫(M.arenaria)和北方根结线虫(M.hapla)。也可以作为杀菌剂，防治多种病原菌。该苯并咪唑衍生物可以有效地控制植物害虫、害螨、线虫和病菌，可以应用在农业上防治病虫害，病原菌。
Description
技术领域
本发明涉及杀虫杀螨技术领域，特别是涉及苯并咪唑衍生物及其制备方法和用途。
背景技术
随着经济社会的发展，人们对农业的经济效益要求越来越高，但是农业害虫害螨的危害严重影响了农产品的产量和质量，例如蚜虫能危害多种植物，并且其分泌的蜜露能引起煤污病；小菜蛾危害白菜、甘蓝等多种十字花科植物，影响蔬菜品质，因此杀灭害虫害螨显得越来越重要。
发明内容
有鉴于此，本发明的目的在于提出一种苯并咪唑衍生物及其制备方法和用途，以有效地控制植物害虫、害螨、线虫和病菌。
基于上述目的，本发明提供的苯并咪唑衍生物的结构式如下：
其中，R1选自H、F、Cl、Br、CH3、NO3中的一种，-OR2取代的位置为邻位、间位和对位中的一种，且R2选自
可选地，所述苯并咪唑衍生物通过以下步骤制得：
将羟基苯甲醛和亚硫酸氢钠溶于乙醇水溶液中，室温下搅拌0.3-0.8小时，抽滤反应得到的混合物，得到羟基苯甲磺酸酸钠；
将所述羟基苯甲磺酸酸钠和取代邻苯二胺溶于N,N-二甲基甲酰胺中，回流1-3小时，然后将反应得到的混合物倒入冰中，抽滤，重结晶得中间体；
将所述中间体和三乙胺溶于二氯甲烷中，冰盐浴冷却至-3～-8℃，将酰氯类化合物溶于二氯甲烷配成酰氯溶液，然后将所述酰氯溶液加入到所述中间体和三乙胺的反应体系中，自然升温至24～28℃，继续搅拌反应1～1.2h；分离反应得到的有机层，然后依次通过水洗、干燥、浓缩和硅胶柱层析分离该有机层，即得到所述苯并咪唑衍生物；
其中，所述取代邻苯二胺的结构式为
所述中间体的结构式为
所述酰氯类化合物的结构式为R2-Cl，
R1选自H、F、Cl、Br、CH3、NO3中的一种，
R2选自
本发明还提供制备上述苯并咪唑衍生物的方法，包括以下步骤：
将羟基苯甲醛和亚硫酸氢钠溶于乙醇水溶液中，室温下搅拌0.3-0.8小时，抽滤反应得到的混合物，得到羟基苯甲磺酸酸钠；
将所述羟基苯甲磺酸酸钠和取代邻苯二胺溶于N,N-二甲基甲酰胺中，回流1-3小时，然后将反应得到的混合物倒入冰中，抽滤，重结晶得中间体；
将所述中间体和三乙胺溶于二氯甲烷中，冰盐浴冷却至-3～-8℃，将酰氯类化合物溶于二氯甲烷配成酰氯溶液，然后将所述酰氯溶液加入到所述中间体和三乙胺的反应体系中，自然升温至24～28℃，继续搅拌反应1～1.2h；分离反应得到的有机层，然后依次通过水洗、干燥、浓缩和硅胶柱层析分离该有机层，即得到所述苯并咪唑衍生物；
其中，所述取代邻苯二胺的结构式为
所述中间体的结构式为
所述酰氯类化合物的结构式为R2-Cl，
R1选自H、F、Cl、Br、CH3、NO3中的一种，
R2选自
可选地，所述羟基苯甲醛选自2-羟基苯甲醛，3-羟基苯甲醛和4-羟基苯甲醛中的一种。
可选地，所述乙醇水溶液中乙醇和水的体积比为1：0.9～1.2。
较佳地，在所述水洗有机层的步骤中，采用水洗涤有机层2～4次，每次洗涤所用水的体积为有机层体积的1.3～1.8倍。
优选地，采用无水硫酸镁干燥所述水洗后的有机层。
可选地，所述硅胶为100～200目，洗脱剂为石油醚和乙酸乙酯，且所述石油醚和乙酸乙酯的体积比为4～1:1。
本发明还提供上述苯并咪唑衍生物的用途，所述苯并咪唑衍生物用于杀虫、杀螨和杀菌。
从上面所述可以看出，本发明了提供一种新型苯并咪唑衍生物，本发明提供的苯并咪唑衍生物可以用于控制多种农业、园林及仓贮有害的昆虫，如鳞翅目、双翅目、同翅目以及一些无脊椎昆虫，如螨类。具体地：Aphisgossypii（棉蚜）、Myzus persicae（桃蚜）、Lipaphis erysimi（菜蚜）Plutellaxylostella（小菜蛾），Nilaparvata lugens（褐飞虱），Tetranychus cinnabarinus（朱砂叶螨）Pieris brassicae（大菜粉蝶），Anopheles spp.(按蚊属)，Culex spp（库蚊属）。也可以用于防治线虫，主要防治植物寄生线虫，如根结线虫，南方根结线虫（M.incognita）、爪哇根结线虫(M.javanica)、花生根结线虫(M.arenaria)和北方根结线虫(M.hapla)。也可以作为杀菌剂，防治多种病原菌。该苯并咪唑衍生物可以有效地控制植物害虫、害螨、线虫和病菌，可以应用在农业上防治病虫害，病原菌。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚明白，以下结合具体实施例，对本发明进一步详细说明。
本发明提供的苯并咪唑衍生物的结构式如下：
其中，R1选自H、F、Cl、Br、CH3、NO3中的一种，-OR2取代的位置为邻位、间位和对位中的一种，且R2选自
部分化合物的具体组合方式参见表1：
表1
本发明还提供所述苯并咪唑衍生物的制备方法，其合成路线如下：
其中，R1选自H、F、Cl、Br、CH3、NO3中的一种，-OR2取代的位置为邻位、间位和对位中的一种，且R2选自
其中，rt即room temperature室温，rf即reflux回流，ice-salt baths冰盐浴。
实施例1（化合物14的制备方法）
将0.04mol（4.88g）对羟基苯甲醛和0.04mol（4.16g）的亚硫酸氢钠溶于40ml乙醇水溶液中（乙醇和水的体积比为1:1），室温下搅拌0.5h。抽滤反应得到的混合物，得7.7g对羟基苯甲磺酸酸钠，收率为86%。
将0.01mol（2.26g）对羟基苯甲磺酸钠和0.01mol（1.08g）邻苯二胺溶于30ml的N,N-二甲基甲酰胺中，回流2h；然后将反应得到的混合物倒入冰中，抽滤，重结晶得1.14g2-(2-羟基苯)-1氢-苯并咪唑，收率为54%。
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.93(d,2H)，7.57(br,1H)，7.55(m,2H)，7.21(m,2H)，6.93(d,2H)，5.35(br,1H)。
将4mmol（0.84g）2-(2-羟基苯)-1氢-苯并咪唑和4mmol（0.42g）的三乙胺溶于8ml二氯甲烷中，冰盐浴冷却至-5℃。将4mmol（0.64g）甲氰菊酰氯溶于8ml二氯甲烷配成0.05mol/l的甲氰菊酰氯溶液，将其缓慢加入2-(2-羟基苯)-1氢-苯并咪唑和三乙胺的反应体系中，自然升温至26℃，继续搅拌反应1h。分离反应得到的有机层，用1.5倍体积的水洗涤有机层3次，然后用无水硫酸镁干燥水洗后的有机层，再过滤、浓缩该有机层，最后用硅胶柱层析分离（100-200目硅胶，洗脱剂为石油醚：乙酸乙酯=4:1-1:1），得到产物1.1g，收率82%。所得产物的结构式为：
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.92(d,2H)，7.59(br,1H)，7.53(m,2H)，7.21(m,2H)，6.93(d,2H)，1.07(d,13H)。
实施例2（化合物15的制备方法）
将0.04mol（4.88g）对羟基苯甲醛和0.04mol（4.16g）的亚硫酸氢钠溶于50ml乙醇水溶液中（乙醇和水的体积比为1:1.2），室温下搅拌0.6h。抽滤反应得到的混合物，得7.7g对羟基苯甲磺酸酸钠，收率为86%。
将0.01mol（2.26g）对羟基苯甲磺酸钠和0.01mol（1.08g）邻苯二胺溶于35ml的N,N-二甲基甲酰胺中，回流1.5h；然后将反应得到的混合物倒入冰中，抽滤，重结晶得1.14g2-(2-羟基苯)-1氢-苯并咪唑，收率为54%。
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.93(d,2H)，7.57(br,1H)，7.55(m,2H)，7.21(m,2H)，6.93(d,2H)，5.35(br,1H)。
将4mmol（0.84g）2-(2-羟基苯)-1氢-苯并咪唑和4mmol（0.42g）的三乙胺溶于7ml二氯甲烷中，冰盐浴冷却至-7℃。4mmol（0.92g）的3-甲基-2-（4-氯苯基）丁酰氯溶于8ml二氯甲烷配成0.05mol/l的3-甲基-2-（4-氯苯基）丁酰氯溶液，将其缓慢加入2-(2-羟基苯)-1氢-苯并咪唑和三乙胺的反应体系中，自然升温至28℃，继续搅拌反应1.2h。分离反应得到的有机层，用1.8倍体积的水洗涤有机层2次，然后用无水硫酸镁干燥水洗后的有机层，再过滤、浓缩该有机层，最后用硅胶柱层析分离（100-200目硅胶，洗脱剂为石油醚：乙酸乙酯=4:1-1:1），得到产物1.2g，收率74%。所得产物的结构式为：
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.96(d,2H)，7.57(br,2H)，7.35(m,4H)，7.24(m,3H)，7.05(d,2H)，3.37(s,1H)，2.44（m，1H），1.17(t,3H)，0.75(m,3H)。
实施例3（化合物30的制备方法）
将0.04mol（4.88g）对羟基苯甲醛和0.04mol（4.16g）的亚硫酸氢钠溶于45ml乙醇水溶液中（乙醇和水的体积比为1:0.9），室温下搅拌0.3h。抽滤反应得到的混合物，得7.7g对羟基苯甲磺酸酸钠，收率为86%。
将0.01mol（2.26g）对羟基苯甲磺酸钠和0.01mol（1.26g）4-氟邻苯二胺溶于30ml的N,N-二甲基甲酰胺中，回流3h；然后将反应得到的混合物倒入冰中，抽滤，重结晶得1.14g2-(2-羟基苯)-1氢-（4-氟）苯并咪唑，收率为50%。
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.93(d,2H)，7.57(br,1H)，7.55(m,2H)，7.21(m,2H)，6.939(d,2H)，5.35(br,1H)。
将4mmol（0.91g）2-(2-羟基苯)-1氢-（4-氟）苯并咪唑和4mmol（0.42g）的三乙胺溶于10ml二氯甲烷中，冰盐浴冷却至-8℃。将4mmol（0.92g）的3-甲基-2-（4-氯苯基）丁酰氯溶于8ml二氯甲烷配成0.05mol/l的3-甲基-2-（4-氯苯基）丁酰氯溶液，将其缓慢加入2-(2-羟基苯)-1氢-（4-氟）苯并咪唑和三乙胺的反应体系中，自然升温至28℃，继续搅拌反应1.1h。分离反应得到的有机层，用1.3倍体积的水洗涤有机层4次，然后用无水硫酸镁干燥水洗后的有机层，再过滤、浓缩该有机层，最后用硅胶柱层析分离（100-200目硅胶，洗脱剂为石油醚：乙酸乙酯=4:1-1:1），得到产物1.2g，收率74%。所得产物的结构式为：
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.98(d,2H)，7.57(br,2H)，7.35(m,4H)，7.24(m,3H)，7.05(d,2H)，3.37(s,1H)，2.44(m，1H)，1.17(t,3H)，0.75(m,3H)。
实施例4（化合物74的制备方法）
将0.04mol（4.88g）对羟基苯甲醛和0.04mol（4.16g）的亚硫酸氢钠溶于38ml乙醇水溶液中（乙醇和水的体积比为1:1.1），室温下搅拌0.8h。抽滤反应得到的混合物，得7.7g对羟基苯甲磺酸酸钠，收率为86%。
将0.01mol（2.26g）对羟基苯甲磺酸钠和0.01mol（1.22g）4-甲基邻苯二胺溶于30ml的N,N-二甲基甲酰胺中，回流1h；然后将反应得到的混合物倒入冰中，抽滤，重结晶得1.1g2-(2-羟基苯)-1氢-（4-甲基）苯并咪唑，收率为51%。
核磁数据1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.93(d,2H)，7.57(br,1H)，7.55(m,2H)，7.21(m,2H)，6.93(d,2H)，5.35(br,1H)，2.34(s,3H)。
将4mmol（0.89g）2-(2-羟基苯)-1氢-（4-甲基）苯并咪唑和4mmol（0.42g）的三乙胺溶于10ml二氯甲烷中，冰盐浴冷却至-3℃。将4mmol（0.64g）甲氰菊酰氯溶于8ml二氯甲烷配成0.05mol/l的甲氰菊酰氯溶液，将其缓慢加入2-(2-羟基苯)-1氢-（4-甲基）苯并咪唑和三乙胺的反应体系中，自然升温至24℃，继续搅拌反应1.1h。分离反应得到的有机层，用1.5倍体积的水洗涤有机层3次，然后用无水硫酸镁干燥水洗后的有机层，再过滤、浓缩该有机层，最后用硅胶柱层析分离（100-200目硅胶，洗脱剂为石油醚：乙酸乙酯=4:1-1:1），得到产物1.1g，收率71%。所得产物的结构式为：
核磁数据：1HNMR，300MHz，内标TMS，溶剂CDCl3，d：7.92(d,2H)，7.59(br,1H)，7.53(m,2H)，7.21(m,2H)，6.93(d,2H)，2.34(s,3H)，1.07(d,13H)。
本发明提供的苯并咪唑衍生物可以用于控制多种农业、园林及仓贮有害的昆虫，如鳞翅目、双翅目、同翅目以及一些无脊椎昆虫，如螨类。具体地：Aphis gossypii（棉蚜）、Myzus persicae（桃蚜）、Lipaphis erysimi（菜蚜）Plutella xylostella（小菜蛾），Nilaparvata lugens（褐飞虱），Tetranychuscinnabarinus（朱砂叶螨）Pieris brassicae（大菜粉蝶），Anopheles spp.(按蚊属)，Culex spp（库蚊属）。
本发明提供的苯并咪唑衍生物可以用于防治线虫，主要防治植物寄生线虫，如根结线虫，南方根结线虫（M.incognita）、爪哇根结线虫(M.javanica)、花生根结线虫(M.arenaria)和北方根结线虫(M.hapla)。
本发明提供的苯并咪唑衍生物也可以作为杀菌剂，防治多种病原菌。
将本发明提供的苯并咪唑衍生物制成多种形式的组合物，如粉剂、可湿性粉剂、粒剂、乳油、悬浮剂等，应用与土壤、植物、种子。为了能够有效地防治有害昆虫、害螨、线虫等，将所述苯并咪唑衍生物制成相应的组合物时，组合物中含有15%-90%质量分数的所述苯并咪唑衍生物。
采用本发明提供的苯并咪唑衍生物对几种昆虫和螨类进行生物活性的测定，测定方法为：苯并咪唑衍生物用二甲基亚砜溶解后，采用含0.1%吐温100的水溶液将苯并咪唑衍生物溶液稀释至所需浓度。
以Myxus persicae（桃蚜），Plutella xylostella（小菜蛾），Nilaparvatalugens（褐飞虱），Tetranychus cinnabarinus（朱砂叶螨）为靶标，采用airbrush喷雾法和浸液法进行杀虫活性鉴定，airbrush喷雾法喷雾压力为10psi(约合0.7kg/cm2)，喷液量为0.5ml，处理后48-72h调查靶标的死亡率。
具体操作过程如下：
（1）对蚜虫的控制（喷雾法）：将20mg苯并咪唑衍生物溶于2ml二甲基亚砜形成10mg/ml的原液，然后用含0.1%吐温100的水溶液将原液稀释至一定浓度。使用手持喷雾器来施用试验溶液，喷洒至含有适当蚜虫（约30-50头蚜虫/叶）的叶片上，直至试验溶液流出叶片两侧。每种化合物每个浓度重复3次。空白对照仅用含0.1%吐温100的水溶液处理。在23℃和相对湿度40%的条件下将叶片保持2-3天，记录每片叶子上蚜虫的总数和死亡数，计算死亡率。
（2）对小菜蛾的控制（浸液法）：将20mg苯并咪唑衍生物溶于2ml二甲基亚砜形成10mg/ml的原液，然后用含0.1%吐温100的水溶液将原液稀释至一定浓度。将圆白菜叶片剪成直径7cm左右的圆片，在一定浓度的试验溶液中浸泡5-10s，取出晾干，每片叶片上放置10-20头小菜蛾，保鲜膜封口，每个浓度的药品重复3次。温度24℃，湿度70%，饲养24-48h，记录每个培养皿的总虫数和死亡虫数。
（3）对褐飞虱的控制（喷雾法和系统试验）：将秧苗浸入在两部分玻璃圆筒底部的水中，底部使用金属网筛支起秧苗，然后使用透明胶带连接玻璃圆筒的两部分，每个处理用三个圆筒。将20mg苯并咪唑衍生物溶于2ml二甲基亚砜中配成10mg/ml的原液，用含0.1%吐温100的水溶液将原液稀释到不同浓度。将0.5ml的试验溶液和溶剂对照以及空白对照喷雾在玻璃圆筒中。系统试验，将原液加入试验秧苗的水中配成不同浓度。在叶面喷雾和系统试验中，施药3h后将褐飞虱3龄若虫引入圆筒中。处理的试验单元（圆筒）置于温度28℃，湿度70%的生长室中，2天和6天进行观察记录。
（4）对朱砂叶螨的控制（药膜法）：将苯并咪唑衍生物用丙酮稀释成不同浓度的药液，每个浓度3个重复，从稀释好的药液中吸取1.2ml加入1.5ml离心管中，轻轻转动离心管，使药剂在管内壁形成均匀的药膜，倒掉多余的药液，放到通风处待丙酮完全挥发，对照单独用丙酮处理，方法相同。每个药膜管中放置30头健康一致的成螨，室内正常饲养条件下24h，检查死亡率。死亡标准：用毛笔轻触虫体，只有1足动或者完全不动即为死亡。对照死亡率小于10%为有效测定。
（5）对按蚊幼虫的控制：将苯并咪唑衍生物用含有0.1%吐温的脱氯自来水稀释成不同浓度的药液，将按蚊幼虫在脱氯的自来水中驯化后，分别挑大小一致、活动迅速的3龄幼虫40头，置于不同浓度的药液中，每个浓度重复3次，以未投药的自来水作为空白对照，计算处理2h后幼虫的死亡率。
测试结果如下：
表2
需要说明的是，可以将本发明提供的苯并咪唑衍生物以组合物的形式使用，用于杀虫、杀螨，所述组合物包含苯并咪唑衍生物和植物学上可接受的载体。可以以喷雾、局部处理、种子包覆、微胶囊、系统吸收、诱饵等多种形式应用所述组合物，以达到控制昆虫的目的。所述组合物可以是浓缩的固体或液体配方（分散在水中即可使用）或者颗粒配方。所述苯并咪唑衍生物的分散体多数是由苯并咪唑衍生物的浓缩配方制成的水悬浮剂或乳液。这些水可溶性、水悬浮性和可乳化性配方是通常被称作可湿性粉剂或可湿性粒剂。它们是活性化合物（即苯并咪唑衍生物）、惰性载体和表面活性剂的均匀混合物，活性化合物的浓度通常是质量分数的10%-90%。载体通常是蒙脱石粘土、硅藻土、硅酸盐以及凸凹棒粘土，占可湿性粉（粒）剂的0.5%-10%。表面活性剂可以是萘磺酸盐、烷基萘磺酸盐、烷基硫酸酯以及非离子型表面活性剂等。
也可以将所述苯并咪唑衍生物溶于合适的有机溶剂中，以溶液形式再分散使用。杀虫杀螨剂通常以活性成分在液体载体中使用，根据活性成分的浓度来确定使用率，载体通常是水。通常活性成分浓度是10mg/kg-5000mg/kg浓度可良好控制，对于多数化合物10mg/kg-500mg/kg就足够。使用化合物的地点可以是昆虫或螨类聚集的任何地点，如蔬菜作物、水果、观赏植物、建筑物的表面、土壤等。本发明的化合物可以与一种或者多种杀虫剂、杀菌剂和除草剂一起施用，也可以相继施用。
由此可见，本发明提供的苯并咪唑衍生物可以有效地控制植物害虫、害螨、线虫和病菌，可以应用在农业上防治病虫害，病原菌。
所属领域的普通技术人员应当理解：以上所述仅为本发明的具体实施例而已，并不用于限制本发明，凡在本发明的精神和原则之内，所做的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。
Claims (9)
1.一种苯并咪唑衍生物，其特征在于，其结构式如下：
其中，R1选自H、F、Cl、Br、CH3、NO3中的一种，-OR2取代的位置为邻位、间位和对位中的一种，且R2选自
2.根据权利要求1所述的苯并咪唑衍生物，其特征在于，所述苯并咪唑衍生物通过以下步骤制得：
将羟基苯甲醛和亚硫酸氢钠溶于乙醇水溶液中，室温下搅拌0.3-0.8小时，抽滤反应得到的混合物，得到羟基苯甲磺酸酸钠；
将所述羟基苯甲磺酸酸钠和取代邻苯二胺溶于N,N-二甲基甲酰胺中，回流1-3小时，然后将反应得到的混合物倒入冰中，抽滤，重结晶得中间体；
将所述中间体和三乙胺溶于二氯甲烷中，冰盐浴冷却至-3～-8℃，将酰氯类化合物溶于二氯甲烷配成酰氯溶液，然后将所述酰氯溶液加入到所述中间体和三乙胺的反应体系中，自然升温至24～28℃，继续搅拌反应1～1.2h；分离反应得到的有机层，然后依次通过水洗、干燥、浓缩和硅胶柱层析分离该有机层，即得到所述苯并咪唑衍生物；
其中，所述取代邻苯二胺的结构式为
所述中间体的结构式为
所述酰氯类化合物的结构式为R2-Cl，
R1选自H、F、Cl、Br、CH3、NO3中的一种，
R2选自
3.一种制备权利要求1所述的苯并咪唑衍生物的方法，其特征在于，包括以下步骤：
将羟基苯甲醛和亚硫酸氢钠溶于乙醇水溶液中，室温下搅拌0.3-0.8小时，抽滤反应得到的混合物，得到羟基苯甲磺酸酸钠；
将所述羟基苯甲磺酸酸钠和取代邻苯二胺溶于N,N-二甲基甲酰胺中，回流1-3小时，然后将反应得到的混合物倒入冰中，抽滤，重结晶得中间体；
将所述中间体和三乙胺溶于二氯甲烷中，冰盐浴冷却至-3～-8℃，将酰氯类化合物溶于二氯甲烷配成酰氯溶液，然后将所述酰氯溶液加入到所述中间体和三乙胺的反应体系中，自然升温至24～28℃，继续搅拌反应1～1.2h；分离反应得到的有机层，然后依次通过水洗、干燥、浓缩和硅胶柱层析分离该有机层，即得到所述苯并咪唑衍生物；
其中，所述取代邻苯二胺的结构式为
所述中间体的结构式为
所述酰氯类化合物的结构式为R2-Cl，
R1选自H、F、Cl、Br、CH3、NO3中的一种，
R2选自
4.根据权利要求3所述的苯并咪唑衍生物的制备方法，其特征在于，所述羟基苯甲醛选自2-羟基苯甲醛，3-羟基苯甲醛和4-羟基苯甲醛中的一种。
5.根据权利要求3所述的苯并咪唑衍生物的制备方法，其特征在于，所述乙醇水溶液中乙醇和水的体积比为1：0.9～1.2。
6.根据权利要求3所述的苯并咪唑衍生物的制备方法，其特征在于，在所述水洗有机层的步骤中，采用水洗涤有机层2～4次，每次洗涤所用水的体积为有机层体积的1.3～1.8倍。
7.根据权利要求6所述的苯并咪唑衍生物的制备方法，其特征在于，采用无水硫酸镁干燥所述水洗后的有机层。
8.根据权利要求3所述的苯并咪唑衍生物的制备方法，其特征在于，所述硅胶为100～200目，洗脱剂为石油醚和乙酸乙酯，且所述石油醚和乙酸乙酯的体积比为4～1:1。
9.根据权利要求1所述的苯并咪唑衍生物的用途，其特征在于，所述苯并咪唑衍生物用于杀虫、杀螨和杀菌。
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