CN102696609B - Trifluoro butene pesticide containing pyridine - Google Patents
Trifluoro butene pesticide containing pyridine Download PDFInfo
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- CN102696609B CN102696609B CN 201210151694 CN201210151694A CN102696609B CN 102696609 B CN102696609 B CN 102696609B CN 201210151694 CN201210151694 CN 201210151694 CN 201210151694 A CN201210151694 A CN 201210151694A CN 102696609 B CN102696609 B CN 102696609B
- Authority
- CN
- China
- Prior art keywords
- pyridine
- insecticides
- acetone
- butylene
- trifluoro
- 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.)
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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
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a trifluoro butene pesticide containing pyridine. The structural formula of the pesticide is represented as formula (1), wherein n=0, 1 and 2. A preparation method of the pesticide is that in the formula (1), n=1 or 2; and when n=0, the pesticide is prepared by undergoing a reaction with an oxidant in inert solvents. The trifluoro butene pesticide containing pyridine is specially used for killing nematode and has the advantages of being remarkable in nematode-killing effect and low in preparation cost and using cost.
Description
Technical field
The present invention relates to agricultural chemicals, is a kind of trifluoro butylene insecticides that contains pyridine.
Background technology
It is the openest as far back as the U.S. that the trifluoro butene compounds has nematicide activity, and afterwards, states such as Japan, China also disclose the multiple nematicidal compound that is different from the United States Patent (USP) structure.These different compounds each have different characteristics when killing nematode.For example: disclosed compound in 00809783.6 patent, though have nematicide performance,, its preparation cost height, and usage amount is higher.
Summary of the invention
The purpose of this invention is to provide a kind of trifluoro butylene insecticides that contains pyridine, it is exclusively used in nematode extremely, and makes it have significant nematicide effect, the advantage that preparation cost and use cost are low.
The present invention is achieved through the following technical solutions for achieving the above object: a kind of trifluoro butylene insecticides that contains pyridine, and the structural formula of this insecticide is:
(1), n=0 wherein, 1,2.
Described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine,
(1), wherein during n=0,6-chloro-3-first sulfydryl pyrrole is fixed
(3) and halogenating agent
(4) in the presence of atent solvent, react and make.
Described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine,
Described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine prepares following insecticide:
Step is as follows: (3) 0.01 moles of 6-chloro-3-first mercaptopyridines are dissolved in 10 milliliters the acetone, add in advance 0.05 mole in the dry potash of crossing, drip 4-bromo-1 at normal temperatures, (4) 0.01 moles of 1,2-, three fluoro-1-butylene are after dropwising, refluxed 48 hours, and filtered, contained
Acetone soln and solid, with acetone drip washing solid 3-5 time, merge the acetone soln that obtains, distill and remove acetone, obtain
(2), obtain yellowish liquid with the chromatography purification, wherein chromatographic solution is n-hexane: the weight ratio of ethyl acetate is 4:6.
Described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine, atent solvent is acetone, N, dinethylformamide (DMF) or dimethyl sulfoxide (DMSO) (DMSO).
Described a kind of application that contains the trifluoro butylene insecticides of pyridine, this insecticide acts on nematode or its habitat.
Insecticide of the present invention has high activity, is exclusively used in nematode extremely, and its nematicide effect is remarkable.It and various crops have favorable compatibility.It can be used for preventing that Pratylenchidae from belonging to; The ball Heterodera: potato is worm completely; Heterodera: soybean cyst nematode; Meloidogyne: aphelenchoides besseyi, similes thorne, fuller's teasel stem eelworm, the nematode of partly puncturing; The minute hand Turbatrix; Xiphinema; The burr Turbatrix; Umbrella Aphelenchoides: pine wood nematode etc.
Insecticide of the present invention can be made regular dosage form: emulsion, an aqueous dispersion material agent, wettable powder, microcapsules etc.
Insecticide preparation method of the present invention does not have special installation and requirement, and preparation cost is low, owing to have high insecticidal activity, can reduce use cost.The present invention draws through measuring the nematicide effect, and control efficiency is remarkable.Test formulation: (structural formula 1, wherein, n=2), 9 parts of kaolin prepare 10% fine granular that contains reactive compound (structural formula 1, wherein n=2) to 1 part of reactive compound.This reagent is used for killing tomato root-knot eelworm.Before the medication; record 50 of every mu of root-knot nematode average out to of plantation tomato protection land used; reagent dosage is 3 liters every mu; reagent inserted contain in the root-knot nematode soil; detect 0.9 of every mu of root-knot nematode after 30 days, insecticidal effect is 99%, and medication detects 1.8 of every mu of root-knot nematodes after 60 days; insecticidal effect is 97%, and above-mentioned insecticidal effect is to use and detect the conclusion that repetition provides for 10 times at reagent.
Embodiment
A kind of trifluoro butylene insecticides that contains pyridine of the present invention, the structural formula of this insecticide is:
(1), n=0 wherein, 1,2.
A kind of preparation method who contains the trifluoro butylene insecticides of pyridine of the present invention,
(1), wherein during n=0,6-chloro-3-first sulfydryl pyrrole is fixed
(3) and halogenating agent
(4) in the presence of atent solvent, react and make.
A kind of preparation method who contains the trifluoro butylene insecticides of pyridine of the present invention, its
(1), wherein n=1 or 2 incites somebody to action
(1), wherein during n=0, reacts under solvent with oxidant and to make.
A kind of preparation method who contains the trifluoro butylene insecticides of pyridine of the present invention, atent solvent is acetone, N, dinethylformamide (DMF) or dimethyl sulfoxide (DMSO) (DMSO).
A kind of application that contains the trifluoro butylene insecticides of pyridine of the present invention, this insecticide acts on nematode or its habitat.
Example 1: prepare following insecticide:
Example 2 prepares following insecticide:
（1），n=1，
Step is as follows: will
(2) 0.01 moles were dissolved in 10 milliliters the methyl alcohol, add 0.01 mole hydrogen peroxide, 30-40 ℃ of reaction 10 hours, add sodium sulphite and destroy remaining oxidant, add ethyl acetate extraction, the distillation desolventizing, purify with chromatography, obtain yellow liquid, wherein chromatographic solution is n-hexane: the ethyl acetate weight ratio is 3:7, elementary analysis: C:42.34% H:3.20%, Cl:12.50%, F:20.09%, N:4.94%, O:5.64%, S:11.30%.
Example 3 prepares following insecticide:
Step is as follows: with in the example 2
(1) n=1,0.01 mole is dissolved in 10 milliliters the methyl alcohol, adds 0.03 mole hydrogen peroxide, refluxed 8 hours, and added sodium sulphite and destroy remaining oxidant, add ethyl acetate extraction, the distillation desolventizing is purified with chromatography, obtains yellow liquid, wherein chromatographic solution is n-hexane: the weight ratio of ethyl acetate is 2:8, elementary analysis: C:40.08%, H:3.03%, Cl:11.83%, F:19.02%, N:4.67%, O:10.68%, S:10.70%..
Claims (6)
1. trifluoro butylene insecticides that contains pyridine, it is characterized in that: the structural formula of this insecticide is:
(1), n=0 wherein, 1,2.
2. the described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine of claim 1, its spy
Levy and be:
(1), wherein during n=0,6-chloro-3-thiopurine methyltransferase pyridine
(3) and halogenating agent
(4) in the presence of atent solvent, react and make.
3. the described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine of claim 1, its spy
Levy and be:
(1), wherein n=1 or 2 incites somebody to action
(1), wherein during n=0, reacts under atent solvent with oxidant and to make.
4. the described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine of claim 2 is characterized in that: prepare following insecticide:
（2），
Step is as follows: (3) 0.01 moles of 6-chloro-3-thiopurine methyltransferase pyridines are dissolved in 10 milliliters the acetone, add in advance 0.05 mole in the dry potash of crossing, drip 4-bromo-1 at normal temperatures, (4) 0.01 moles of 1,2-, three fluoro-1-butylene are after dropwising, refluxed 48 hours, and filtered, contained
Acetone soln and solid, with acetone drip washing solid 3-5 time, merge the acetone soln that obtains, distill and remove acetone, obtain
(2), obtain yellowish liquid with the chromatography purification, wherein chromatographic solution is n-hexane: the weight ratio of ethyl acetate is 4:6.
5. the described a kind of preparation method who contains the trifluoro butylene insecticides of pyridine of claim 2, it is characterized in that: atent solvent is acetone, N, dinethylformamide (DMF) or dimethyl sulfoxide (DMSO) (DMSO).
6. the described a kind of application that contains the trifluoro butylene insecticides of pyridine of claim 1, it is characterized in that: this insecticide acts on nematode or its habitat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210151694 CN102696609B (en) | 2012-01-10 | 2012-05-16 | Trifluoro butene pesticide containing pyridine |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210005777.8 | 2012-01-10 | ||
| CN201210005777 | 2012-01-10 | ||
| CN 201210151694 CN102696609B (en) | 2012-01-10 | 2012-05-16 | Trifluoro butene pesticide containing pyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102696609A CN102696609A (en) | 2012-10-03 |
| CN102696609B true CN102696609B (en) | 2013-09-11 |
Family
ID=46889897
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201210151694 Active CN102696609B (en) | 2012-01-10 | 2012-05-16 | Trifluoro butene pesticide containing pyridine |
| CN201210198040.2A Active CN102696593B (en) | 2012-01-10 | 2012-06-15 | Benzene-ring-containing trifluorobutene insecticides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210198040.2A Active CN102696593B (en) | 2012-01-10 | 2012-06-15 | Benzene-ring-containing trifluorobutene insecticides |
Country Status (2)
| Country | Link |
|---|---|
| CN (2) | CN102696609B (en) |
| WO (1) | WO2013104170A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106554335B (en) * | 2015-09-30 | 2017-09-19 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring of transconfiguration and its production and use |
| CN109845741A (en) * | 2018-11-26 | 2019-06-07 | 刘西芳 | Nematicidal composition containing furfural |
| CN114075300B (en) * | 2020-08-21 | 2023-02-28 | 佛山市海力盈生物科技有限公司 | Chitosan oligosaccharide derivative nematicide and preparation method and application thereof |
| CN120591275B (en) * | 2025-08-06 | 2025-10-28 | 南开大学 | Application of Inhibition of Farnesol Dehydrogenase in Enhancing the Toxicity of Trifluoxetine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86104207A (en) * | 1985-06-20 | 1987-04-01 | Fmc有限公司 | The pesticidal use of many halogen alkene derivatives |
| CN87104606A (en) * | 1986-06-30 | 1988-01-13 | Fmc有限公司 | S-trifluoro butenyl derivative and pesticidal use |
| CN1143958A (en) * | 1994-03-10 | 1997-02-26 | 曾尼卡有限公司 | Pesticidally active (4,4-difluorobut-3-enylthio)-substituted heterocyclic or carbocyclic compounds |
| CN1359379A (en) * | 1999-07-06 | 2002-07-17 | 日本拜耳农药株式会社 | Nematicidal trifluorobutenes |
| CN1476437A (en) * | 2000-03-09 | 2004-02-18 | �ձ��ݶ�ũҩ��ʽ���� | trifluorobutene |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3654293A (en) * | 1969-11-20 | 1972-04-04 | Stauffer Chemical Co | 2- and 4-(3 4 4-trifluoro-3-butenyl-thio)pyridines |
| DK0640069T3 (en) * | 1991-03-01 | 1999-07-19 | Monsanto Co | Fluoroalkenyl compounds and their use as agents for the control of harmful organisms |
| CN101516878A (en) * | 2006-09-13 | 2009-08-26 | 住友化学株式会社 | Thiadiazole compound and use thereof |
-
2012
- 2012-05-16 CN CN 201210151694 patent/CN102696609B/en active Active
- 2012-06-07 WO PCT/CN2012/076560 patent/WO2013104170A1/en not_active Ceased
- 2012-06-15 CN CN201210198040.2A patent/CN102696593B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86104207A (en) * | 1985-06-20 | 1987-04-01 | Fmc有限公司 | The pesticidal use of many halogen alkene derivatives |
| CN87104606A (en) * | 1986-06-30 | 1988-01-13 | Fmc有限公司 | S-trifluoro butenyl derivative and pesticidal use |
| CN1143958A (en) * | 1994-03-10 | 1997-02-26 | 曾尼卡有限公司 | Pesticidally active (4,4-difluorobut-3-enylthio)-substituted heterocyclic or carbocyclic compounds |
| CN1359379A (en) * | 1999-07-06 | 2002-07-17 | 日本拜耳农药株式会社 | Nematicidal trifluorobutenes |
| CN1476437A (en) * | 2000-03-09 | 2004-02-18 | �ձ��ݶ�ũҩ��ʽ���� | trifluorobutene |
Non-Patent Citations (4)
| Title |
|---|
| 具有杀线虫活性的三氟丁烯类化合物研究进展;沈德隆等;《浙江化工》;20050228;第36卷(第02期);22-24 * |
| 崔永梅等.生物电子等排原理在药物先导化合物优化中的应用.《生命科学》.2006,第18卷(第02期),161-167. |
| 沈德隆等.具有杀线虫活性的三氟丁烯类化合物研究进展.《浙江化工》.2005,第36卷(第02期),22-24. |
| 生物电子等排原理在药物先导化合物优化中的应用;崔永梅等;《生命科学》;20060415;第18卷(第02期);161-167 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102696593A (en) | 2012-10-03 |
| CN102696593B (en) | 2014-07-02 |
| CN102696609A (en) | 2012-10-03 |
| WO2013104170A1 (en) | 2013-07-18 |
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