CN109232343A - 一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法及其在杀虫剂中的应用 - Google Patents

一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法及其在杀虫剂中的应用 Download PDF

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CN109232343A
CN109232343A CN201811241066.4A CN201811241066A CN109232343A CN 109232343 A CN109232343 A CN 109232343A CN 201811241066 A CN201811241066 A CN 201811241066A CN 109232343 A CN109232343 A CN 109232343A
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aromatic hydrocarbons
alkane
trifluoroethyl
selenide
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CN109232343B (zh
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翁志强
董静楠
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Fuzhou University
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Abstract

本发明属于涉及到农作物害虫的杀虫剂领域，具体涉及一种铜催化合成芳烃/烷烃2,2,2‑三氟乙基硒醚的方法及该类化合物在杀虫剂中的应用。以碘化亚铜为催化剂，双亚胺为双齿配体，芳烃/烷烃卤素、硒粉以及2,2,2‑三氟碘乙烷为反应物，硼氢化钠为还原剂，在N,N‑二甲基甲酰胺溶剂中，95‑110℃下搅拌1‑24小时，反应结束后反应液后处理得到2,2,2‑三氟乙基硒醚化合物。本发明的合成方法具有催化剂价廉易得且毒性小，原料易得，操作简便，官能团普适性好等优点。该类含氟化合物对小菜蛾、朱砂叶螨等具有很好活性，在600 mg/L剂量下，对害虫的死亡率高达100%，可作为一种新型、高效的含氟杀虫剂。

Description

一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法及其 在杀虫剂中的应用
技术领域
本发明属于有机合成领域，涉及到农作物害虫的杀虫剂领域，具体涉及一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法及该类化合物在杀虫剂中的应用。
背景技术
现代农业的发展，要求开发的新农药必须具有高安全性、低残留、无公害、生物活性高、高选择性、低成本的特性。含氟基团具有强的吸电子性和高亲酯性，往往表现出许多非常独特的物理性质和化学性质。往有机分子中引入含氟基团后，会增强分子的亲酯性，促进其在生物体内的吸收和传输。在众多含氟基团化合物中，对含2,2,2-三氟乙硒基化合物的研究较少。另一方面，有机硒化合物具有良好的生物活性,如抗感染、抗癌、抗辐射等。
发明内容
本发明的目的在于提供一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法，该法原料廉价易得，产率高，官能团的适应性很好，且其反应操作简便，该类含氟化合物对小菜蛾、朱砂叶螨等具有很好活性，可作为一种新型、高效的杀虫剂。
为实现上述目的，本发明采用如下技术方案：
一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法，以碘化亚铜为催化剂，双亚胺为双齿配体，芳烃/烷烃卤素、硒粉以及2,2,2-三氟碘乙烷为反应物，硼氢化钠为还原剂，在N,N-二甲基甲酰胺溶剂中反应制得芳烃/烷烃2,2,2-三氟乙基硒醚，可用于农业杀虫剂（杀虫剂剂型可制备成液体、缓释剂或粉末），化学反应式是：
所述的芳烃卤素的结构式为： ，X为Br或I，所述的芳烃2,2,2-三氟乙基硒醚的结构式为：，R为下述式1-式27中的任意一种：
所述的双亚胺的结构式为：。
所述的碘化亚铜、双亚胺配体、芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷和硼氢化钠的摩尔比为0.1-1: 0.1-1:1:1-2:1-3:1-2。
优选地，所述的碘化亚铜、双亚胺配体、芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷和硼氢化钠的摩尔比为0.1:0.1:1:1:2:1。
所述芳烃/烷烃2,2,2-三氟乙基硒醚的制备方法具体包括以下步骤：
向带有磁力搅拌装置的容器中加入碘化亚铜、双亚胺配体、芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷、硼氢化钠和N,N-二甲基甲酰胺, 混合均匀后关好塞子，将其放入95-110℃油浴中继续搅拌1-24小时，用二氯甲烷萃取，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到芳烃/烷烃2,2,2-三氟乙基硒醚。
本发明的有益效果在于：
本发明以工业上廉价易得的芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷等为原料，以碘化亚铜为催化剂合成芳烃/烷烃2,2,2-三氟乙基硒醚，得到普遍较高的产率，官能团的适应性很好，且其反应操作简便，本发明中的2,2,2-三氟乙基硒醚类化合物对小菜蛾、朱砂叶螨等均具有很好活性，在600 mg/L剂量下，对害虫的死亡率高达100%，可作为一种新型、高效的含氟杀虫剂。
具体实施方式
为了使本发明所述的内容更加便于理解，下面结合具体实施方式对本发明所述的技术方案做进一步的说明，但是本发明不仅限于此。
合成方法
实施例1
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 4-碘苯甲酸甲酯，0.50 mmol 硒粉，1.0 mmol2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到4-(2,2,2-三氟乙硒基)苯甲酸甲酯（分离产率68%）。1H NMR (400 MHz, CDCl3) δ 7.81 (dd, J = 132.4, 7.3 Hz, 4H), 3.94 (s, 3H),3.46 (q, J = 10.3 Hz, 2H)。19F NMR (376 MHz, CDCl3) δ -64.4 (t, J = 10.4 Hz,3F)。GC-MS m/z 297 (M+)。
实施例2
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 2-氰基碘苯，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到2-(2,2,2-三氟乙硒基)苯甲腈（分离产率98%）。1HNMR (400 MHz, CDCl3) δ 7.83 (d, J = 7.8 Hz, 1H), 7.73 (d, J = 7.6 Hz, 1H),7.56 (t, J = 7.7 Hz, 1H), 7.49 (t, J = 7.6 Hz, 1H), 3.52 (q, J = 10.2 Hz,2H)。 19F NMR (376 MHz, CDCl3δ -64.3 (t, J = 10.2 Hz,3F))。GC-MS m/z 265 (M+)。
实施例3
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 1-碘萘，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到1-(2,2,2-三氟乙基)萘硒醚（分离产率91%）。1H NMR(400 MHz, CDCl3) δ 8.49 (d, J = 8.4 Hz, 1H), 8.03 (d, J = 7.1 Hz, 1H), 7.92(t, 2H), 7.62 (dt, J = 27.4, 7.4 Hz, 2H), 7.44 (t, J = 7.7 Hz, 1H), 3.41 (q,J = 10.5 Hz, 2H)。19F NMR (376 MHz, CDCl3) δ -64.1 (t, J = 10.5 H,3F)。GC-MS m/z290 (M+)。
实施例4
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 3-氟碘苯，0.50 mmol 硫粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到3-(2,2,2-三氟乙硒基)氟苯（分离产率83%）。1H NMR(400 MHz, CDCl3) δ 7.41 (d, J = 7.7 Hz, 1H), 7.38 – 7.26 (m, 2H), 7.06 (t, J= 8.4 Hz, 1H), 3.41 (q, J = 10.3 Hz, 2H)。19F NMR (376 MHz, CDCl3) δ -64.5 (t,J = 10.3 Hz,3F)), -111.3 (m, J = 14.5, 8.4 Hz,1F)。GC-MS m/z 257 (M+)。
实施例5
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 2-溴-4-甲基吡啶，0.50 mmol 硒粉，1.0 mmol2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺,在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到2-(2，2，2-三氟乙硒基)-4-甲基吡啶（分离产率81%）。1H NMR (400 MHz, CDCl3) δ 8.34 (d, J = 4.8 Hz, 1H), 7.21 (s, 1H), 6.93(d, J = 4.7 Hz, 1H), 3.95 (q, J = 10.6 Hz, 2H), 2.32 (s, 3H)。19F NMR (376 MHz,CDCl3) δ -64.5 (t, J = 10.7 Hz,3F)。GC-MS m/z 254(M+)。
实施例6
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 2-溴-6-氰基吡啶，0.50mmol 硒粉，1.0 mmol2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到2-(2,2,2-三氟乙硒基)-6-氰基吡啶（分离产率75%）。1H NMR (400 MHz, CDCl3) δ 7.66 (t, J = 7.8 Hz, 1H), 7.58 (d, J = 8.1Hz, 1H), 7.52 (d, J = 7.4 Hz, 1H), 3.96 (q, J = 10.5 Hz, 2H)。19F NMR (376 MHz,CDCl3) δ -64.4 (t, J = 10.5 Hz,3F)。GC-MS m/z 266 (M+)。
实施例7
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 2-溴苯并噻唑，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到2-(2，2，2-三氟乙硒基)苯并噻唑（分离产率55%）。1H NMR (400 MHz, CDCl3) δ 8.00 (d, J = 8.1 Hz, 1H), 7.82 (d, J = 7.9 Hz,1H), 7.48 (t, J = 7.4 Hz, 1H), 7.37 (t, J = 7.4 Hz, 1H), 4.08 (q, J = 9.9 Hz,2H)。 19F NMR (376 MHz, CDCl3) δ -64.3 (t, J = 10.3 Hz,3F)。GC-MS m/z 296 (M+)。
实施例8
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 4-氰基碘苯，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到4-(2，2，2-三氟乙基)氰基苯硒醚（分离产率74%）1HNMR (400 MHz, CDCl3) δ 7.64 (dd, J = 33.2, 7.6 Hz, 4H), 3.48 (q, J = 9.6 Hz,2H)。19F NMR (376 MHz, CDCl3) δ -64.4 (t, J = 10.1 Hz,3F)。GC-MS m/z 265 (M+)。
实施例9
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 3-氯碘苯，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中95℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到3-(2,2,2-三氟乙硒基)氯苯（分离产率77%）。1H NMR(400 MHz, CDCl3) δ 7.64 (s, 1H), 7.52 (d, J = 7.6 Hz, 1H), 7.34 (d, J = 7.9Hz, 1H), 7.29 – 7.21 (m, 1H), 3.40 (q, J = 9.9 Hz,2H)。 19F NMR (376 MHz,CDCl3) δ -64.4 (t, J = 10.3 Hz,3F)。GC-MS m/z 273 (M+)。
实施例10
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 2-溴乙基苯，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中110℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到2-(2,2,2-三氟乙硒基)乙基苯（分离产率84%）。1HNMR (400 MHz, CDCl3) δ 7.34 (t, J = 7.1 Hz, 2H), 7.24 (t, J = 9.7 Hz, 3H),3.08 (q, J = 10.5 Hz, 2H), 2.78 (dd, J = 13.4, 6.5 Hz, 4H), 2.05 (p, J = 7.1Hz, 2H)。19F NMR (376 MHz, CDCl3) δ -64.5 (t, J = 10.6 Hz,3F)。GC-MS m/z 282 (M+)。
实施例11
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉， 0.50 mmol 7-溴庚腈，0.50 mmol 硒粉，1.0 mmol 2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中110℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到7-(2,2,2-三氟乙硒基)庚腈（分离产率58%）。1HNMR (400 MHz, CDCl3) δ 3.07 (q, J = 9.9 Hz, 2H), 2.76 (t, J = 6.8 Hz, 2H),2.37 (t, J = 6.6 Hz, 2H), 1.70 (dt, J = 18.9, 6.4 Hz, 4H), 1.57 – 1.41 (m,4H)。19F NMR (376 MHz, CDCl3) δ -64.5 (t, J = 10.5 Hz,3F)。GC-MS m/z 272 (M+)。
实施例12
在氮气气氛中，在一个反应器中放入聚四氟乙烯磁石一粒，再加入0.050 mmol 碘化亚铜，0.050 mmol 1,10-邻菲罗啉，0.50 mmol 4-苯氧基溴丁烷，0.50 mmol 硒粉，1.0 mmol2,2,2-三氟碘乙烷，0.50 mmol 硼氢化钠，最后加入5 mL N,N-二甲基甲酰胺，在密闭体系中110℃搅拌反应16 h后，冷却至室温，用二氯甲烷萃取3次，每次15 mL，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到4-苯氧基-(2,2,2-三氟乙硒基)丁烷（分离产率77%）。1H NMR (400 MHz, CDCl3) δ 7.33 (t, J = 7.6 Hz, 2H), 6.99 (t, J = 7.3Hz, 1H), 6.93 (d, J = 8.0 Hz, 2H), 4.02 (t, J = 4.8 Hz, 2H), 3.10 (q, J =10.6 Hz, 2H), 2.85 (s, 2H), 1.93 (s, 4H)。19F NMR (376 MHz, CDCl3) δ -64.5 (t,J = 10.6 Hz,3F)。GC-MS m/z 312 (M+)。
杀虫活性试验
实施例1：杀小菜蛾的测定方法
在培养皿（Ф=6 cm）底覆一层滤纸，滴加适量自来水保湿，备用。取温室培养的甘蓝叶片，除去表面蜡质层，用打孔器制成甘蓝叶碟（Ф=3 cm），叶背向上置于培养皿中。按试验设计，用Airbrush手持式喷雾设备将600 mg/L化合物2-(2,2,2-三氟乙硒基)芴待测液（溶剂和0.1%的吐温-80自来水配制）及10 mg/L阿维菌素药液均匀喷雾于叶片正反面（喷雾压力：0.7 kg/cm2，喷液量：0.5 ml；喷雾距离：15-20 cm），另设清水处理作为空白对照。待叶片自然阴干后，接入小菜蛾3龄幼虫。将培养皿移至标准观察室内（温度为23-25 ℃，RH=40-60%，L/D为13 h/11 h）培养，72 h后进行调查，记录试虫的死虫与活虫数，计算死亡率为50%。
实施例2：杀朱砂叶螨的测定方法
在培养皿（Ф=6 cm）底覆一层滤纸，滴加适量自来水保湿，备用。处理前24 h，选择两片真叶的菜豆苗，移栽于培养杯中，每杯一株。待移栽苗正常生长后，于处理前3 h，剪去心叶及一片真叶。按试验设计，用Airbrush手持式喷雾设备将600 mg/L化合物2-(2,2,2-三氟乙硒基)芴待测液（溶剂和0.1%的吐温-80自来水配制）及10 mg/L阿维菌素药液均匀喷雾于叶片正反面（喷雾压力：0.7 kg/cm2，喷液量：0.5 ml；喷雾距离：15-20 cm），另设清水处理作为空白对照。待叶片自然阴干后，接入适量的雌成螨，并记录基数，作为测定寄主和靶标。将培养皿移至标准观察室内（温度为23-25 ℃，RH=40-60%，L/D为13 h/11 h）培养，72 h后进行调查，记录试虫的死虫与活虫数，计算死亡率为100%。
以上所述仅为本发明的较佳实施例，凡依本发明申请专利范围所做的均等变化与修饰，皆应属本发明的涵盖范围。

Claims (7)

1.一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法，其特征在于：以碘化亚铜为催化剂，双亚胺为双齿配体，芳烃/烷烃卤素、硒粉以及2,2,2-三氟碘乙烷为反应物，以硼氢化钠为还原剂，在N,N-二甲基甲酰胺溶剂中反应制得芳烃/烷烃2,2,2-三氟乙基硒醚，所述的芳烃卤素的结构式为：，X为Br或I；所述的2,2,2-三氟乙基硒醚类化合物的结构式为：。
2.根据权利要求1所述的一种铜催化合成芳烃2,2,2-三氟乙基硒醚的方法，其特征在于：芳烃/烷烃卤素结构式中的R为下述式1-式27中的任意一种：
。
3.根据权利要求1所述的一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法，其特征在于：所述双亚胺的结构式为：。
4.根据权利要求1所述的一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法，其特征在于：碘化亚铜、双亚胺、芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷和硼氢化钠的摩尔比为0.1-1: 0.1-1:1:1-2:1-3:1-2。
5.根据权利要求4所述的一种铜催化合成芳烃/烷烃2,2,2-三氟乙基硒醚的方法，其特征在于：碘化亚铜、双亚胺、芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷和硼氢化钠的摩尔比为0.1:0.1:1:1:2:1。
6.根据权利要求1所述的合成方法，其特征在于：具体步骤如下：向带有磁力搅拌装置的容器中加入碘化亚铜、双亚胺、芳烃/烷烃卤素、硒粉、2,2,2-三氟碘乙烷、硼氢化钠和N,N-二甲基甲酰胺，混合均匀后关好塞子，将其放入95-110℃油浴中继续搅拌1-24小时，用二氯甲烷萃取，合并有机相，用蒸馏水洗涤3次，有机相用无水硫酸镁干燥，过滤，然后旋蒸除去有机溶剂；得到的粗产物通过硅胶柱层析，以正戊烷为洗脱剂进行洗脱，得到芳烃/烷烃2,2,2-三氟乙基硒醚。
7.根据权利要求1所述方法制备的一种2,2,2-三氟乙基硒醚类化合物在杀虫剂中的应用。
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