CN101367784B - 丙烯腈类化合物及其制备方法和应用 - Google Patents
丙烯腈类化合物及其制备方法和应用 Download PDFInfo
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- CN101367784B CN101367784B CN2008101562689A CN200810156268A CN101367784B CN 101367784 B CN101367784 B CN 101367784B CN 2008101562689 A CN2008101562689 A CN 2008101562689A CN 200810156268 A CN200810156268 A CN 200810156268A CN 101367784 B CN101367784 B CN 101367784B
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- 238000002360 preparation method Methods 0.000 title abstract description 10
- 150000008360 acrylonitriles Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- -1 acrylonitrile compound Chemical class 0.000 claims abstract description 67
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 18
- 239000002917 insecticide Substances 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 230000000895 acaricidal effect Effects 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000000642 acaricide Substances 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000008282 halocarbons Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000007962 benzene acetonitriles Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000002635 aromatic organic solvent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 241000238631 Hexapoda Species 0.000 abstract description 8
- 150000001263 acyl chlorides Chemical class 0.000 abstract description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract 3
- 239000000470 constituent Substances 0.000 abstract 2
- 241000934067 Acarus Species 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- 241000238876 Acari Species 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000000575 pesticide Substances 0.000 description 10
- 241001124076 Aphididae Species 0.000 description 9
- 235000010749 Vicia faba Nutrition 0.000 description 9
- 240000006677 Vicia faba Species 0.000 description 9
- 235000002098 Vicia faba var. major Nutrition 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000003226 pyrazolyl group Chemical group 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 5
- 238000003898 horticulture Methods 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- QKJPXROEIJPNHG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC=C(CC#N)C=C1 QKJPXROEIJPNHG-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000258937 Hemiptera Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- 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 3
- 239000012044 organic layer Substances 0.000 description 3
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009363 floriculture Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
化合物No. | 1HNMR(CDCl3)δ |
1 | E:1.35(s,9H),1.50(d,3H,J=6.6Hz),1.95(s,3H),2.28(s,3H),2.84(m,1H),3.28(m,1H),4.96(m,1H),7.06-7.51(m,6H)Z:1.26(s,9H),1.46(d,3H,J=6.6Hz),2.11(s,3H),2.28(s,3H),2.84(m,1H),3.28(m,1H),4.96(m,1H),7.06-7.51(m,6H) |
2 | 1.02(d,6H,J=6.6Hz),1.34(s,9H),1.43(d,3H,J=6.6Hz),2.19(d,2H,J=6.6Hz),2.35(s,3H),2.47(m,1H),2.84(m,1H),3.28(m,1H),4.96(m,1H),7.08-7.59(m,6H) |
3 | 1.34(s,9H),1.43(d,3H,J=6.6Hz),2.35(s,3H),2.84(m,1H),3.28(m,1H),4.96(m,1H),6.81-8.19(m,11H) |
4 | 1.06(d,1H,J=8.1Hz),1.11(s,6H),1.34(s,9H),1.43(d,3H,J=6.6Hz),1.51(q,1H,J=8.7Hz),2.35(s,3H),2.84(m,1H),3.28(m,1H),4.96(m,1H),5.63(d,1H,J=9.0Hz),6.81-7.44(m,6H) |
5 | 1.09(t,3H,J=8.7Hz),1.34(s,9H),1.43(d,3H,J=6.6Hz),2.27(q,2H,J=8.7Hz),2.35(s,3H),2.84(m,1H),3.28(m,1H),4.96(m,1H),7.05-7.67(m,6H) |
6 | 1.16(d,6H,J=6.6Hz),1.34(s,9H),1.43(d,3H,J=6.6Hz),2.35(s,3H),2.74(m,1H),2.84(m,1H),3.28(m,1H),4.96(m,1H),7.00~7.67(m,6H) |
7 | 1.24(s,9H),1.34(s,9H),1.43(d,3H,J=6.6Hz),2.35(s,3H),2.84(m,1H), |
3.28(m,1H),4.96(m,1H),6.96~7.56(m,6H) | |
8 | 1.30(s,9H),1.43(d,3H,J=6.6Hz),2.29(s,3H),2.92(s,1H),2.84(m,1H),3.28(m,3H),4.96(m,1H),6.96~7.56(m,6H) |
9 | E:1.28(t,3H,J=7.5Hz),2.20(s,3H),2.95(q,2H,J=7.5Hz),4.01(s,3H),7.11~7.55(m,4H)Z:1.21(t,3H,J=7.5Hz),2.29(s,3H),2.64(q,2H,J=7.5Hz),3.86(s,3H),7.11~7.55(m,4H) |
10 | E:0.90(d,6H,J=6.6Hz),1.27(t,3H,J=7.5Hz),2.20(m,1H),2.42(d,2H,J=6.6Hz),2.63(q,2H,J=7.5Hz),3.98(s,3H),7.07~7.54(m,4H)Z:1.02(d,6H,J=6.6Hz),1.23(t,3H,J=7.5Hz),2.24(m,1H),2.47(d,2H,J=6.6Hz),2.59(q,2H,J=7.5Hz),3.38(s,3H),7.07~7.54(m,4H) |
11 | 1.13~1.29(m,6H),2.38(q,2H,J=6.6Hz),2.62(q,2H,J=7.5Hz),3.98(s,3H),7.07~7.32(m,4H) |
12 | 1.21~1.29(m,12H),2.68(q,2H,J=7.5Hz),4.00(s,3H),7.28~7.62(m,4H) |
13 | 1.24(t,3H,J=7.5Hz),2.62(q,2H,J=7.5Hz),2.98(s,3H),3.87(s,3H),7.09~8.05(m,4H) |
14 | 1.07~1.36(m,10H),1.67(q,1H,J=8.7Hz),2.65(q,2H,J=7.5Hz),3.97(s,3H),5.63(d,1H,J=9.0Hz),7.20~7.57(m,4H) |
15 | 1.17~1.34(m,9H),2.60(q,2H,J=7.5Hz),3.40(m,1H),3.996(s,3H),7.30~7.56(m,4H) |
16 | 1.25(t,3H,J=7.5Hz),2.65(q,2H,J=7.5Hz),4.05(s,3H),7.37~8.18(m,9H) |
17 | E:1.20~1.39(m,6H),2.93(q,2H,J=7.5Hz),3.90(s,3H),4.21(q,2H,J=6.6Hz),7.09~7.99(m,4H)Z:1.20~1.39(m,6H),2.63(q,2H,J=7.5Hz),3.90(s,3H),4.31(q,2H,J=6.6Hz),7.09~7.99(m,4H) |
18 | 1.24(t,3H,J=7.5Hz),2.61(q,2H,J=7.5Hz),3.45(s,3H),7.13~8.11(m,8H) |
19 | E:1.25(t,3H,J=7.5Hz),2.62(q,2H,J=7.5Hz),3.88(s,3H),4.04(s,3H),7.14~7.64(m,8H)Z:1.25(t,3H,J=7.5Hz),2.62(q,2H,J=7.5Hz),3.88(s,3H),3.47(s,3H),7.14~7.64(m,8H) |
20 | E:1.23(t,3H,J=7.5Hz),1.25(m,6H),2.97(q,2H,J=7.5Hz),3.86—4.27(m,7H),7.33—7.95(m,4H)Z:1.22(t,3H,J=7.5Hz),1.35(m,6H),2.65(q,2H,J=7.5Hz),3.86—4.27(m,7H), |
7.33—7.95(m,4H) | |
21 | 1.14~1.41(m,18H),2.69(q,2H,J=7.5Hz),3.92(s,3H),4.15(q,4H,J=6.6Hz),7.02~7.73(m,4H) |
22 | 1.14~1.41(m,18H),2.66(q,2H,J=7.5Hz),3.96(s,3H),4.14(q,4H,J=6.6Hz),7.27~7.88(m,4H) |
23 | 1.14~1.40(m,15H),2.28(s,3H),4.08(s,3H),4.24(q,4H,J=6.6Hz),7.37~7.78(m,4H) |
24 | 1.22~1.35(m,12H),2.08(s,3H),2.63(q,2H,J=7.5Hz),3.29(s,3H),7.06~7.40(m,4H) |
25 | 1.11~1.37(m,18H),2.66(q,2H,J=7.5Hz),3.96(s,3H),4.26(q,4H,J=6.6Hz),6.50(s,1H),7.25~7.69(m,4H) |
26 | 1.22~1.35(m,12H),2.11(s,3H),2.66(q,2H,J=7.5Hz),3.96(s,3H),6.73(s,1H),7.27~7.50(m,4H) |
No. | 72h死亡率% | No. | 72h死亡率% | No. | 72h死亡率% | No. | 72h死亡率% |
1 | 29.88 | 8 | 33.89 | 15 | 80.95 | 22 | 89.67 |
2 | 0 | 9 | 100 | 16 | 74.00 | 23 | 100 |
3 | 15.35 | 10 | 100 | 17 | 100 | 24 | 100 |
4 | 73.71 | 11 | 80.20 | 18 | 75.00 | 25 | 100 |
5 | 33.07 | 12 | 100 | 19 | 76.00 | 26 | 100 |
6 | 21.95 | 13 | 65.53 | 20 | 48.63 | ||
7 | 8.07 | 14 | 100 | 21 | 100 |
No. | 72h死亡率% | No. | 72h死亡率% | No. | 72h死亡率% | No. | 72h死亡率% |
1 | 10.54 | 8 | 52.14 | 15 | 13.19 | 22 | 62.29 |
2 | 83.29 | 9 | 38.27 | 16 | 18.92 | 23 | 100 |
3 | 1.92 | 10 | 1.23 | 17 | 16.96 | 24 | 49.79 |
4 | 0 | 11 | 40.16 | 18 | 10.34 | 25 | 100 |
5 | 11.11 | 12 | 32.11 | 19 | 36.29 | 26 | 83.01 |
6 | 86.67 | 13 | 38.70 | 20 | 87.07 | ||
7 | 42.86 | 14 | 7.25 | 21 | 78.09 |
No. | 72h死亡率% | No. | 72h死亡率% | No. | 72h死亡率% | No. | 72h死亡率% |
1 | 72.50 | 8 | 85.00 | 15 | 5.00 | 22 | 100 |
2 | 45.00 | 9 | 2.50 | 16 | 2.50 | 23 | 100 |
3 | 47.50 | 10 | 0 | 17 | 0 | 24 | 5.00 |
4 | 90.00 | 11 | 0 | 18 | 2.50 | 25 | 100 |
5 | 80.00 | 12 | 15.00 | 19 | 75.00 | 26 | 7.50 |
6 | 75.00 | 13 | 0 | 20 | 100 | ||
7 | 72.50 | 14 | 2.50 | 21 | 100 |
Claims (11)
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CN101875633B (zh) | 2009-04-29 | 2012-01-18 | 中国中化股份有限公司 | 吡唑基丙烯腈类化合物及其应用 |
CN102786473A (zh) * | 2011-05-18 | 2012-11-21 | 中国中化股份有限公司 | 1-乙烯基吡唑类化合物及其应用 |
CN103651381B (zh) * | 2012-09-24 | 2016-03-30 | 沈阳中化农药化工研发有限公司 | 一种杀螨制剂及其应用 |
CN105766923B (zh) * | 2014-12-25 | 2018-12-14 | 沈阳中化农药化工研发有限公司 | 一种杀虫、螨组合物 |
CN105766924B (zh) * | 2014-12-25 | 2019-01-15 | 沈阳中化农药化工研发有限公司 | 一种含杀菌剂或杀细菌(病毒)剂的杀虫、杀螨组合物 |
CN108570008B (zh) * | 2017-03-14 | 2020-07-28 | 浙江省化工研究院有限公司 | 一类吡唑类衍生物、其制备方法及应用 |
CN109553577A (zh) * | 2018-12-20 | 2019-04-02 | 西安近代化学研究所 | 一种吡唑类化合物及制备方法和应用 |
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