CN105037329A - 一种含氟四嗪吡唑类杀螨剂 - Google Patents
一种含氟四嗪吡唑类杀螨剂 Download PDFInfo
- Publication number
- CN105037329A CN105037329A CN201510559100.2A CN201510559100A CN105037329A CN 105037329 A CN105037329 A CN 105037329A CN 201510559100 A CN201510559100 A CN 201510559100A CN 105037329 A CN105037329 A CN 105037329A
- Authority
- CN
- China
- Prior art keywords
- mite
- fluorine
- compound
- reaction
- miticide
- 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.)
- Granted
Links
- 239000000642 acaricide Substances 0.000 title claims abstract description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 18
- 239000011737 fluorine Substances 0.000 title claims abstract description 18
- 230000000895 acaricidal effect Effects 0.000 title abstract description 6
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 title abstract description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title abstract 2
- 241000238876 Acari Species 0.000 claims abstract description 6
- -1 tetrazine pyrazole compound Chemical class 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 235000013601 eggs Nutrition 0.000 abstract 1
- 230000002147 killing effect Effects 0.000 abstract 1
- 230000000452 restraining effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 29
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 14
- 108010000912 Egg Proteins Proteins 0.000 description 10
- 102000002322 Egg Proteins Human genes 0.000 description 10
- 210000004681 ovum Anatomy 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RGUAEBDOGUUAIE-UHFFFAOYSA-N CCC1(CC(C=CC1Cl)(C)C(=O)O)C(=O)O Chemical compound CCC1(CC(C=CC1Cl)(C)C(=O)O)C(=O)O RGUAEBDOGUUAIE-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000036039 immunity Effects 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical class NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 description 2
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005654 Clofentezine Substances 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 description 1
- MVSWPVFMSKKBAW-UHFFFAOYSA-N 1,4-dihydro-1,2,4,5-tetrazine Chemical compound N1C=NNC=N1 MVSWPVFMSKKBAW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 description 1
- SWBHWUYHHJCADA-UHFFFAOYSA-N 3-(2-chlorophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazine Chemical compound FC1=CC=CC(F)=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 SWBHWUYHHJCADA-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052956 cinnabar Inorganic materials 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201510559100.2A CN105037329B (zh) | 2015-09-06 | 2015-09-06 | 一种含氟四嗪吡唑类杀螨剂 |
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CN201510559100.2A CN105037329B (zh) | 2015-09-06 | 2015-09-06 | 一种含氟四嗪吡唑类杀螨剂 |
Publications (2)
Publication Number | Publication Date |
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CN105037329A true CN105037329A (zh) | 2015-11-11 |
CN105037329B CN105037329B (zh) | 2017-03-22 |
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Family Applications (1)
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CN201510559100.2A Active CN105037329B (zh) | 2015-09-06 | 2015-09-06 | 一种含氟四嗪吡唑类杀螨剂 |
Country Status (1)
Country | Link |
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CN (1) | CN105037329B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017036427A3 (zh) * | 2015-09-06 | 2017-04-13 | 浙江博仕达作物科技有限公司 | 一种四嗪吡唑类杀螨剂 |
CN109336879A (zh) * | 2018-11-07 | 2019-02-15 | 青岛科技大学 | 一种3-吡啶基-1,2,4-噁二唑类化合物及其应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1156536A (zh) * | 1996-02-07 | 1997-08-13 | 河北省石油化学工业研究所 | 哒螨酮和四螨嗪复合农药的悬浮剂 |
WO2000078739A1 (en) * | 1999-06-21 | 2000-12-28 | Syngenta Participations Ag | Pesticidally active tetrazine derivatives |
WO2015016372A1 (ja) * | 2013-07-31 | 2015-02-05 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
CN104447074A (zh) * | 2014-12-30 | 2015-03-25 | 尤素梅 | 一种绿色环保、复合多功能植物叶面肥的制备方法及应用 |
-
2015
- 2015-09-06 CN CN201510559100.2A patent/CN105037329B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1156536A (zh) * | 1996-02-07 | 1997-08-13 | 河北省石油化学工业研究所 | 哒螨酮和四螨嗪复合农药的悬浮剂 |
WO2000078739A1 (en) * | 1999-06-21 | 2000-12-28 | Syngenta Participations Ag | Pesticidally active tetrazine derivatives |
WO2015016372A1 (ja) * | 2013-07-31 | 2015-02-05 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
CN104447074A (zh) * | 2014-12-30 | 2015-03-25 | 尤素梅 | 一种绿色环保、复合多功能植物叶面肥的制备方法及应用 |
Non-Patent Citations (1)
Title |
---|
BROOKER, PETER J.等: "Acaricidal 1,2,4,5-tetrazines", 《PESTICIDE SCIENCE》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017036427A3 (zh) * | 2015-09-06 | 2017-04-13 | 浙江博仕达作物科技有限公司 | 一种四嗪吡唑类杀螨剂 |
CN109336879A (zh) * | 2018-11-07 | 2019-02-15 | 青岛科技大学 | 一种3-吡啶基-1,2,4-噁二唑类化合物及其应用 |
CN109336879B (zh) * | 2018-11-07 | 2021-08-17 | 青岛科技大学 | 一种3-吡啶基-1,2,4-噁二唑类化合物及其应用 |
Also Published As
Publication number | Publication date |
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CN105037329B (zh) | 2017-03-22 |
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Address after: 475500, 400 meters south of Miqi Road, Airport Economic Comprehensive Experimental Zone, Zhengzhou City, Henan Province Patentee after: HeNan K-Land Agriculture Development Co.,Ltd. Country or region after: China Address before: 475500 south of Miyi Road, Daying Town, Weishi County, Kaifeng City, Henan Province Patentee before: Kaifeng Yitian Biotechnology Co.,Ltd. Country or region before: China |
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