CN103483246B - 一种苄基磺酰亚胺衍生物及其应用 - Google Patents
一种苄基磺酰亚胺衍生物及其应用 Download PDFInfo
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- 241000344246 Tetranychus cinnabarinus Species 0.000 claims abstract description 13
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
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- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
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- 229940125904 compound 1 Drugs 0.000 description 2
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- SCBZBMXPJYMXRC-UHFFFAOYSA-N 1-(bromomethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CBr)=C1 SCBZBMXPJYMXRC-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000272317 Lipaphis erysimi Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
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- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical group BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- Wood Science & Technology (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
本发明公开了属于化学农药技术领域的一种苄基磺酰亚胺衍生物及其在杀灭农业害虫中的应用。本发明的苄基磺酰亚胺衍生物，为首次发现和人工合成，可以有效杀灭棉蚜、桃蚜、菜蚜、小菜蛾，褐飞虱，朱砂叶螨，按蚊等农业害虫，对人体毒害小，易被环境降解。
Description
技术领域
本发明属于化学农药技术领域，具体涉及一种苄基磺酰亚胺衍生物及其在杀灭农业害虫中的应用。
背景技术
在农业生产中，桃蚜、小菜蛾、褐飞虱、朱砂叶螨、按蚊等农业害虫和螨虫对农作物的危害很大，难以根治。
近年来专利US2008194634，WO2010074751，WO2010074747，US2003176468都公开了苄基磺酰亚胺衍生物，这些衍生物具有杀虫活性，有的还具有杀菌和除草活性。然而，本发明中的苄基磺酰亚胺衍生物未见报道。
发明内容
本发明的目的在于提供一种苄基磺酰亚胺衍生物。
本发明的目的还在于提供上述苄基磺酰亚胺衍生物在杀灭农业害虫中的应用。
一种苄基磺酰亚胺衍生物，其结构式如下：
其中，X为Cl，CF3，F，Br，OCH3或OCF3；Y为Br，Cl，NO2，OCH3，OCF3，F或H；R为CH3或H。
上述化合物形成的盐，可以为化合物的钠盐，钾盐或盐酸盐。
一种杀虫、杀螨组合物，包含上述化合物中的一种或一种以上的组合，所占重量百分比为0.1-99％。
上述化合物在防治农业害虫中的应用。
所述农业害虫为蚜虫，螨虫，飞蛾，蚊类和飞虱。
所述蚜虫为桃蚜，棉蚜及菜蚜；所述螨虫为朱砂叶螨；所述飞蛾为小菜蛾；所述蚊类为按蚊；所述飞虱为褐飞虱。
上述化合物的合成路线：
本发明涉及的苄基磺酰亚胺衍生物，部分化合物见表1。
表1
| 编号 | X | R | Y |
| 1 | Cl | H | Br |
| 2 | Cl | H | Cl |
| 3 | Cl | H | NO2 |
| 4 | Cl | H | OCH3 |
| 5 | Cl | H | OCF3 |
| 6 | Cl | H | F |
| 7 | Cl | H | H |
| 8 | Cl | CH3 | Br |
| 9 | Cl | CH3 | Cl |
| 10 | Cl | CH3 | NO2 |
| 11 | Cl | CH3 | OCH3 |
| 12 | Cl | CH3 | OCF3 |
| 13 | Cl | CH3 | F |
| 14 | Cl | CH3 | H |
| 15 | CF3 | H | Br |
| 16 | CF3 | H | Cl |
| 17 | CF3 | H | NO2 |
| 18 | CF3 | H | OCH3 |
| 19 | CF3 | H | OCF3 |
| 20 | CF3 | H | F |
| 21 | CF3 | H | H |
| 22 | CF3 | CH3 | Br |
| 23 | CF3 | CH3 | Cl |
| 24 | CF3 | CH3 | NO2 |
| 25 | CF3 | CH3 | OCH3 |
| 26 | CF3 | CH3 | OCF3 |
| 27 | CF3 | CH3 | F |
| 28 | CF3 | CH3 | H |
| 29 | F | H | Br |
| 30 | F | H | Cl |
| 31 | F | H | NO2 |
| 32 | F | H | OCH3 |
| 33 | F | H | OCF3 |
| 34 | F | H | F |
| 35 | F | H | H |
| 36 | F | CH3 | Br |
| 37 | F | CH3 | Cl |
| 38 | F | CH3 | NO2 |
| 39 | F | CH3 | OCH3 |
| 40 | F | CH3 | OCF3 |
| 41 | F | CH3 | F |
| 42 | F | CH3 | H |
| 43 | Br | H | Br |
| 44 | Br | H | Cl |
| 45 | Br | H | NO2 |
| 46 | Br | H | OCH3 |
| 47 | Br | H | OCF3 |
| 48 | Br | H | F |
| 49 | Br | H | H |
| 50 | Br | CH3 | Br |
| 51 | Br | CH3 | Cl |
| 52 | Br | CH3 | NO2 |
| 53 | Br | CH3 | OCH3 |
| 54 | Br | CH3 | OCF3 |
| 55 | Br | CH3 | F |
| 56 | Br | CH3 | H |
| 57 | OCH3 | H | Br |
| 58 | OCH3 | H | Cl |
| 59 | OCH3 | H | NO2 |
| 60 | OCH3 | H | OCH3 |
| 6l | OCH3 | H | OCF3 |
| 62 | OCH3 | H | F |
| 63 | OCH3 | H | H |
| 64 | OCH3 | CH3 | Br |
| 65 | OCH3 | CH3 | Cl |
| 66 | OCH3 | CH3 | NO2 |
| 67 | OCH3 | CH3 | OCH3 |
| 68 | OCH3 | CH3 | OCF3 |
| 69 | OCH3 | CH3 | F |
| 70 | OCH3 | CH3 | H |
| 71 | OCF3 | H | Br |
| 72 | OCF3 | H | Cl |
| 73 | OCF3 | H | NO2 |
| 74 | OCF3 | H | OCH3 |
| 75 | OCF3 | H | OCF3 |
| 76 | OCF3 | H | F |
| 77 | OCF3 | H | H |
| 78 | OCF3 | CH3 | Br |
| 79 | OCF3 | CH3 | Cl |
| 80 | OCF3 | CH3 | NO2 |
| 81 | OCF3 | CH3 | OCH3 |
| 82 | OCF3 | CH3 | OCF3 |
| 83 | OCF3 | CH3 | F |
| 84 | OCF3 | CH3 | H |
本发明的有益效果：本发明的苄基磺酰亚胺衍生物，为首次发现和人工合成，可以有效杀灭Aphisgossypii(棉蚜)、Myzuspersicae(桃蚜)、Lipaphiserysimi(菜蚜)、Plutellaxylostella(小菜蛾)，Nilaparvatalugens(褐飞虱)，Tetranychuscinnabarinus(朱砂叶螨)，按蚊等农业害虫，对人体毒害小，易被环境降解。
具体实施方式
下面结合具体实施例对本发明做进一步说明。
实施例1化合物1的合成
化合物1的结构式为：
在100ml的单口烧瓶中加3.25g(0.02mol)2氯-5氯甲基吡啶，加入50ml的无水乙醇溶解，加入3.42g(0.03mol)硫代乙酸钾室温下搅拌4h，减压得到的残余物倒入水中，二氯甲烷萃取3次，取下层有机相，用饱和食盐水(200ml*3)洗涤，有机相用无水硫酸镁干燥，过滤，旋蒸，过柱(硅胶200-300目，洗脱剂为石油醚：乙酸乙酯=8：1)纯化，得到黄色的液体产物2.7g，产率68％。1HNMR(300MHz，CDC13)δ(非对映异构体混合物)8.3(s，1H)，7.6(d，1H)，7.2(d，1H)，4，(m，2H)，2.4(s，3H)；
将黄色溶液溶于20ml无水乙醇中，加入邻氯苄溴2.74g(0.014mol)和2.78g(0.02mol)K2CO3，室温下反应6h，过滤旋蒸，冷乙醇结晶，得到黄色晶体2.43g(61％)。δ(非对映异构体混合物)8.5(d，1H)，7.9(m，1H)，7.7(m，1H)，7.2(m，4H)，3.7(s，4H)；
在25mL单口瓶中加入上述黄色晶体(2.43g，0.008mol)，加入四氢呋喃10mL搅拌，冰水浴降温至0℃。然后分别加入氰胺(0.34g，0.008mol)和醋酸碘苯(2.58g，0.008mol)，此温度下搅拌3h后室温搅拌过夜，第2天将反应液直接过滤，得到的白色固体1.23g，产率48％。δ(非对映异构体混合物)8.5(d，1H)，7.9(m，1H)7.7(m，1H)，7.4(m，3H)2.2(s，4H)；
在25mL单口瓶中加入间氯过氧苯甲酸(0.98g，0.0057mol)，加入乙醇10mL搅拌，冰水浴降温至0℃搅拌10min，然后将无水碳酸钾(0.79g，0.0057mol)
的10mL水溶液一次性加入，有大量白色固体析出。0℃搅拌20min后将上述白色固体(1.23g，0.0038mol)的6mL乙醇溶液一次性加入，搅拌5min后将反应液淬于水中。然后用乙酸乙酯萃取3次，有机层分别用水和饱和食盐水洗涤3次，有机层经无水硫酸镁干燥，过滤，旋蒸到有固体析出，进行过滤，得到白色固体既为所要产物。δ(非对映异构体混合物)8.2(b，2H)，7.5(b，2H)，7.3(m，3H)，3.8(b，4H)。
实施例2化合物2的合成
化合物2的结构式为：
在100ml的单口烧瓶中加3.25g(0.02mol)2氯-5氯甲基吡啶，加入50ml的无水乙醇溶解，加入3.42g(0.03mol)硫代乙酸钾室温下搅拌4h，减压得到的残余物倒入水中，二氯甲烷萃取3次，取下层有机相，用饱和食盐水(200*3)洗涤，有机相用无水硫酸镁干燥，过滤，旋蒸，过柱(硅胶200-300目，洗脱剂为石油醚：乙酸乙酯=8：1)纯化，得到黄色的液体产物2.7g，产率68％。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.3(s，1H)，7.6(s，1H)，7.2(s，1H)，4，(s，2H)，2.4(s，3H)；
将黄色溶液溶于20ml无水乙醇中，加入3-氟苄溴3.8g(0.02mol)和2.78g(0.02mol)K2CO3，室温下反应6h，过滤旋蒸，冷乙醇结晶，得到白色晶体2.44g(产率68％)。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.5(s，1H)，7.9(d，1H)，7.4(s，1H)，7.3(m，4H)，3.8(s，4H)；
在25mL单口瓶中加入上述白色晶体(2.44g，0.009mol)，加入四氢呋喃10mL搅拌，冰水浴降温至0℃。然后分别加入氰胺(0.38g，0.009mol)和醋酸碘苯(2.9g，0.009mol)，此温度下搅拌3h后室温搅拌过夜，第2天将反应液直接过滤，得到的白色固体1.57g(产率56％)。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.5(s，1H)，7.9(d，1H)，7.4(s，1H)，7.3(m，4H)，3.9-4.0(m，2H)，3.5-3.7(m，2H)；
在25mL单口瓶中加入间氯过氧苯甲酸(1.29g，0.0075mol)，加入乙醇10mL搅拌，冰水浴降温至0℃搅拌10min，然后将无水碳酸钾(1.06g，0.0075mol)的10mL水溶液一次性加入，有大量白色固体析出。0℃搅拌20min后将上述白色固体的(1.57g，0.005mol)的6mL乙醇溶液一次性加入，搅拌5min后将反应液淬于水中。然后用乙酸乙酯萃取3次，有机层分别用水和饱和食盐水洗涤3次，有机层经无水硫酸镁干燥，过滤，旋蒸到有固体析出，进行过滤，得到白色固体既为所要产物。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.5(s，1H)，7.9(d，1H)，7.4(s，1H)，7.3(m，4H)，4.2(s，2H)，4.0(s，2H)。
实施例3化合物3的合成
化合物3的结构式为：
在100ml的单口烧瓶中加4.32g(0.02mol)2-甲氧基-5-(1-溴)-乙基-吡啶，加入50ml的无水乙醇溶解，加入3.42g(0.03mol)硫代乙酸钾室温下搅拌4h，减压得到的残余物倒入水中，二氯甲烷萃取3次，取下层有机相，用饱和食盐水(200*3)洗涤，有机相用无水硫酸镁干燥，过滤，旋蒸，过柱(硅胶200-300目，洗脱剂为石油醚：乙酸乙酯=8：1)纯化，得到黄色的液体产物2.91g，产率69％。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)7.6(d，1H)，7.4(s，1H)，6.5(d，1H)，4.3，(m，1H)，3.8(s，3H)，2.3(s，3H)，1.61(d，3H)；
将黄色溶液溶于20ml无水乙醇中，加入邻硝基苄溴1.89g(0.02mol)和1.9g(0.02mol)K2CO3，室温下反应6h，过滤旋蒸，冷乙醇结晶，得到白色晶体2.13g(产率51％)。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.0(d，H)，7.7(m，2H)，7.6(m，1H)，7.4(m，1H)，6.5(d，1H)，4.0(m，1H)，3.8(s，3H)，3.7(d，2H)，1.6(m，3H)；
在25mL单口瓶中加入上述白色晶体(2.13g，0.007mol)，加入四氢呋喃10mL搅拌，冰水浴降温至0℃。然后分别加入氰胺(0.29g，0.007mol)和醋酸碘苯(2.25g，0.007mol)，此温度下搅拌3h后室温搅拌过夜，第2天将反应液直接过滤，得到的白色固体1.77g(产率74％)。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.2(d，1H)，7.7(m，2H)，7.6(m，1H)，7.4(m，1H)，6.5(d，1H)，3.8(s，3H)，3.0(m，1H)，1.2(m，3H)，1.0(d，2H)；
在25mL单口瓶中加入间氯过氧苯甲酸(0.86g，0.005mol)，加入乙醇10mL搅拌，冰水浴降温至0℃搅拌10min，然后将无水碳酸钾(0.71g，0.005mol)的10mL水溶液一次性加入，有大量白色固体析出。0℃搅拌20min后将上述白色固体的(1.77g，0.005mol)的6mL乙醇溶液一次性加入，搅拌5min后将反应液淬于水中。然后用乙酸乙酯萃取3次，有机层分别用水和饱和食盐水洗涤3次，有机层经无水硫酸镁干燥，过滤，旋蒸到有固体析出，进行过滤，得到白色固体既为所要产物。1HNMR(300MHz，CDCl3)δ(非对映异构体混合物)8.4(d，1H)，7.9(m，2H)，7.7(m，1H)，7.4(m，1H)，6.5(d，1H)，4.0(m，H)3.8(d，5H)，1.6(d，3H)。
实施例4化合物生物活性的测定
新化合物用DMSO溶解后，用含0.1％的吐温100的水稀释至所需浓度。
Myxuspersicae(桃蚜)，Plutellaxylostella(小菜蛾)，Nilaparvatalugens(褐飞虱)，Tetranychuscinnabarinus(朱砂叶螨)，按蚊为靶标，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)对桃蚜的控制(喷雾法)：将20mg化合物溶于2mlDMSO形成10000mg／kg的原液。然后用含0.1％吐温100的水稀释原液至一定浓度。使用手持喷雾器来施用试验溶液，喷洒至含有适当桃蚜(约30-50头桃蚜／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％的吐温100水液处理。在23℃和40％RH条件下将叶片保持2-3天，记录每片叶子上桃蚜的总数和死亡数，计算死亡率。
(2)对朱砂叶螨的控制(喷雾法)：将20mg化合物溶于2mlDMSO形成10000mg／kg的原液。然后用含0.1％吐温100的水稀释原液至一定浓度。使用手持喷雾器来施用试验溶液，喷洒至含有适当朱砂叶螨(约80-100头朱砂叶螨／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％的吐温100水液处理。在23℃和40％RH条件下将叶片保持2-3天，记录每片叶子上朱砂叶螨的总数和死亡数，计算死亡率。
(3)对小菜蛾的控制(浸液法)：将20mg化合物溶于2mlDMSO形成10000mg／kg的原液。然后用含0.1％吐温100的水稀释原液至一定浓度。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。
(4)对按蚊的控制(浸液法)：将20mg化合物溶于2mlDMSO形成10000mg／kg的原液。然后用含0.1％吐温100的水稀释原液至一定浓度。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15-25头按蚊，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。
(5)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。装置好秧苗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。试验化合物溶于DMSO中配成10000mg／kg原液，用含0.1％吐温100的水稀释到不同浓度。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。
表2
测试结果如表2所示，供试化合物均对桃蚜，小菜蛾，褐飞虱，朱砂叶螨，按蚊有良好的杀灭作用。
本发明的化合物可以组合物的形式使用，而且是本发明的重要实施方式，包含本发明所含的化合物和植物学上可接受的载体。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本发明的化合物达到控制昆虫的目的。所述组合物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，虽然按照农业化学的传统方法和配方配置制组合物，但是他们是新型的重要的。为了确保农业化学工作者能容易制备任何所学的组合物，我们给出了所述组合物配制的一些说明。
这些化合物的分散体多数是由化合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、惰性载体、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l0％-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％。表面活性剂有萘磺酸盐、烷基萘磺酸盐、烷基硫酸酯以及非离子型表面活性剂。
出于任何原因需要，可以将化合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。
使用到昆虫和螨类所在地的量并不重要，可根据上述实例确定。通常是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。
Claims (1)
1.一种苄基磺酰亚胺衍生物在防治农业害虫中的应用，其特征在于，所述农业害虫为朱砂叶螨；
所述苄基磺酰亚胺衍生物的结构式如下：
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| US20100076032A1 (en) * | 2004-04-08 | 2010-03-25 | Dow Agrosciences Llc | Insecticidal n-substituted sulfoximines |
| CN102264224A (zh) * | 2008-12-26 | 2011-11-30 | 美国陶氏益农公司 | 稳定的亚磺酰亚胺杀虫剂组合物 |
| WO2013037894A1 (en) * | 2011-09-16 | 2013-03-21 | Bayer Intellectual Property Gmbh | Disubstituted 5-fluoro pyrimidine derivatives containing a sulfoximine group |
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