CN102696609B - 一种含吡啶的三氟丁烯类杀虫剂 - Google Patents
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 48
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 24
- WCNKHTIPPVQEQW-UHFFFAOYSA-N 4,4,4-trifluorobut-1-ene Chemical compound FC(F)(F)CC=C WCNKHTIPPVQEQW-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000000575 pesticide Substances 0.000 title abstract 6
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 241000244206 Nematoda Species 0.000 claims abstract description 8
- 239000007800 oxidant agent Substances 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- 239000002917 insecticide Substances 0.000 claims description 34
- -1 trifluoro butylene Chemical group 0.000 claims description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- 238000011097 chromatography purification Methods 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 229940072033 potash Drugs 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 102000016397 Methyltransferase Human genes 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 150000003222 pyridines Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 239000012442 inert solvent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000005645 nematicide Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000243785 Meloidogyne javanica Species 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 241001480224 Heterodera Species 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000196508 Turbatrix Species 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000294569 Aphelenchoides Species 0.000 description 1
- 241000134843 Aphelenchoides besseyi Species 0.000 description 1
- 241000243771 Bursaphelenchus xylophilus Species 0.000 description 1
- 241001073847 Dipsacus fullonum Species 0.000 description 1
- 0 FC(CC*Cc(cn1)ccc1I1CC1)=C(F)F Chemical compound FC(CC*Cc(cn1)ccc1I1CC1)=C(F)F 0.000 description 1
- 241000498254 Heterodera glycines Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000193945 Pratylenchidae Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000201423 Xiphinema Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
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Abstract
本发明提供了一种含吡啶的三氟丁烯类杀虫剂，该杀虫剂的结构式为：
（1），其中n=0,1,2。其制备方法：
（1），其中n=1或2，将
Description
技术领域
本发明涉及农药，是一种含吡啶的三氟丁烯类杀虫剂。
背景技术
三氟丁烯化合物具有杀线虫的活性最早在美国公开，之后，日本、中国等国也公开了多种不同于美国专利结构的杀线虫化合物。这些不同的化合物在杀线虫时，各自有不同的特点。例如：00809783.6专利中公开的化合物，虽然具有杀线虫的性能，但是，它的制备成本高，并且使用量较高。
发明内容
本发明的目的是提供一种含吡啶的三氟丁烯类杀虫剂，它专用于杀线虫，并使其具有显著的杀线虫的效果，制备成本和使用成本低的优点。
本发明为实现上述目的，通过以下技术方案实现：一种含吡啶的三氟丁烯类杀虫剂，该杀虫剂的结构式为： 
（1），其中n=0,1,2。
所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，
（1），其中n=0时，6-氯-3-甲巯基吡定（3）和卤化剂
（4）在惰性溶剂存在下进行反应制得。
所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，
所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，制备下述杀虫剂：
步骤如下：将6-氯-3-甲巯基吡啶（3）0.01摩尔溶解在10毫升的丙酮中，加入预先干燥过的碳酸钾0.05摩尔，在常温下滴加4-溴-1,1,2-三氟-1-丁烯（4）0.01摩尔，滴加完毕后，回流48小时，过滤，得到含
的丙酮溶液和固体，用丙酮淋洗固体3-5次，合并得到的丙酮溶液，蒸馏去丙酮，得到
（2），用层析法提纯得到淡黄的液体，其中层析液为正己烷：乙酸乙酯的重量比为4:6。
所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，惰性溶剂为丙酮、N,N-二甲基甲酰胺（DMF)或二甲基亚砜（DMSO)。
所述的一种含吡啶的三氟丁烯类杀虫剂的应用，该杀虫剂作用于线虫或其栖息地。
本发明所述的杀虫剂具有极高的活性，专用于杀线虫，其杀线虫的效果显著。它与各种农作物有良好的兼容性。它可用于防止短体线虫属；球异皮线虫属：马铃薯全线虫；异皮线虫属：大豆异皮线虫；根结线虫属：水稻干尖线虫，穿孔线虫，起绒草茎线虫，半穿刺线虫；长针线虫属；剑线虫属；毛刺线虫属；伞滑刃线虫属：松材线虫等。
本发明所述杀虫剂可以制成常规剂型：乳液、水分散颗料剂、可湿粉剂、微胶囊等。
本发明所述的杀虫剂制备方法无特殊设备及要求，制备成本低，由于具有极高的杀虫活性，可降低使用成本。本发明经过测定杀线虫药效得出，防治效果显著。测试制剂：1份活性化合物(结构式1 ，其中，n=2),9份高岭土，制备得到含活性化合物（结构式1，其中n=2）的10%精细颗粒。该试剂用于杀番茄根结线虫。用药前，测得种植番茄保护用地每亩根结线虫平均为50条，试剂用量为每亩3公升，将试剂置入含根结线虫土壤中，30天后检出每亩根结线虫0.9条，杀虫效果为99%，用药60天后检出每亩根结线虫1.8条，杀虫效果为97%，上述杀虫效果是在试剂使用和检测重复10次给出的结论。
具体实施方式
本发明所述的一种含吡啶的三氟丁烯类杀虫剂，该杀虫剂的结构式为： 
（1），其中n=0,1,2。
本发明所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法， 
（1），其中n=0时，6-氯-3-甲巯基吡定
（3）和卤化剂
（4）在惰性溶剂存在下进行反应制得。
本发明所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，其
（1），其中n=1或2，将
（1），其中n=0时，与氧化剂在溶剂下进行反应制得。
本发明所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，惰性溶剂为丙酮、N,N-二甲基甲酰胺（DMF)或二甲基亚砜（DMSO)。
本发明所述的一种含吡啶的三氟丁烯类杀虫剂的应用， 该杀虫剂作用于线虫或其栖息地。
例1：制备下述杀虫剂：
例2，制备下述杀虫剂：
（1），n=1，
步骤如下：将
（2）0.01摩尔溶解在10毫升的甲醇中，加入0.01摩尔的双氧水，在30-40℃反应10小时，加亚硫酸钠破坏残余氧化剂，加乙酸乙酯萃取，蒸馏去溶剂，用层析法提纯，得到黄色的液体，其中层析液为正己烷：乙酸乙酯重量比为3:7，元素分析：C:42.34% H:3.20%,Cl:12.50%,F:20.09%,N:4.94%,O:5.64%,S:11.30% 。
例3，制备下述杀虫剂：
步骤如下：将例2中的
（1）n=1，0.01摩尔溶解在10毫升的甲醇中，加入0.03摩尔的双氧水，回流8小时，加亚硫酸钠破坏残余氧化剂，加乙酸乙酯萃取，蒸馏去溶剂，用层析法提纯，得到黄色的液体，其中层析液为正己烷：乙酸乙酯的重量比为2:8，元素分析：C:40.08%,H:3.03%,Cl:11.83%,F:19.02%,N:4.67%,O:10.68%,S:10.70%.。
Claims (6)
1.一种含吡啶的三氟丁烯类杀虫剂，其特征在于：该杀虫剂的结构式为： 
（1），其中n=0,1,2。
2.权利要求1所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，其特
征在于：
（1），其中n=0时，6-氯-3-巯甲基吡啶（3）和卤化剂
（4）在惰性溶剂存在下进行反应制得。
3.权利要求1所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，其特
征在于：
（1），其中n=1或2，将
（1），其中n=0时，与氧化剂在惰性溶剂下进行反应制得。
4.权利要求2所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，其特征在于：制备下述杀虫剂：
（2），
步骤如下：将6-氯-3-巯甲基吡啶（3）0.01摩尔溶解在10毫升的丙酮中，加入预先干燥过的碳酸钾0.05摩尔，在常温下滴加4-溴-1,1,2-三氟-1-丁烯（4）0.01摩尔，滴加完毕后，回流48小时，过滤，得到含的丙酮溶液和固体，用丙酮淋洗固体3-5次，合并得到的丙酮溶液，蒸馏去丙酮，得到
（2），用层析法提纯得到淡黄的液体，其中层析液为正己烷：乙酸乙酯的重量比为4:6。
5.权利要求2所述的一种含吡啶的三氟丁烯类杀虫剂的制备方法，其特征在于：惰性溶剂为丙酮、N,N-二甲基甲酰胺（DMF)或二甲基亚砜（DMSO)。
6.权利要求1所述的一种含吡啶的三氟丁烯类杀虫剂的应用，其特征在于：该杀虫剂作用于线虫或其栖息地。
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| CN106554335B (zh) * | 2015-09-30 | 2017-09-19 | 山东省联合农药工业有限公司 | 一种反式结构的含内酯环的杀线虫剂及其制备方法和用途 |
| CN109845741A (zh) * | 2018-11-26 | 2019-06-07 | 刘西芳 | 含糠醛的杀线虫组合物 |
| CN114075300B (zh) * | 2020-08-21 | 2023-02-28 | 佛山市海力盈生物科技有限公司 | 一类壳寡糖衍生物杀线剂及其制备方法和应用 |
| CN120591275B (zh) * | 2025-08-06 | 2025-10-28 | 南开大学 | 抑制法尼醇脱氢酶在增效三氟杀线酯毒力中的应用 |
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| CN86104207A (zh) * | 1985-06-20 | 1987-04-01 | Fmc有限公司 | 多卤烯烃衍生物的杀虫用途 |
| CN87104606A (zh) * | 1986-06-30 | 1988-01-13 | Fmc有限公司 | S-三氟丁烯基衍生物及杀虫用途 |
| CN1143958A (zh) * | 1994-03-10 | 1997-02-26 | 曾尼卡有限公司 | 具有农药活性的(4，4-二氟丁-3-烯基硫基)-取代的杂环或碳环类化合物 |
| CN1359379A (zh) * | 1999-07-06 | 2002-07-17 | 日本拜耳农药株式会社 | 杀线虫的三氟丁烯化合物 |
| CN1476437A (zh) * | 2000-03-09 | 2004-02-18 | �ձ��ݶ�ũҩ��ʽ���� | 杀线虫的三氟丁烯 |
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| US3654293A (en) * | 1969-11-20 | 1972-04-04 | Stauffer Chemical Co | 2- and 4-(3 4 4-trifluoro-3-butenyl-thio)pyridines |
| DK0640069T3 (da) * | 1991-03-01 | 1999-07-19 | Monsanto Co | Fluoralkenylforbindelser og deres anvendelse som midler til bekæmpelse af skadelige organismer |
| CN101516878A (zh) * | 2006-09-13 | 2009-08-26 | 住友化学株式会社 | 噻二唑化合物及其用途 |
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- 2012-06-07 WO PCT/CN2012/076560 patent/WO2013104170A1/zh not_active Ceased
- 2012-06-15 CN CN201210198040.2A patent/CN102696593B/zh active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102696593A (zh) | 2012-10-03 |
| CN102696593B (zh) | 2014-07-02 |
| CN102696609A (zh) | 2012-10-03 |
| WO2013104170A1 (zh) | 2013-07-18 |
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