CN1446196A - 酰基乙腈化合物,其制备方法及包含该化合物的杀螨剂 - Google Patents
酰基乙腈化合物,其制备方法及包含该化合物的杀螨剂 Download PDFInfo
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- CN1446196A CN1446196A CN01814040A CN01814040A CN1446196A CN 1446196 A CN1446196 A CN 1446196A CN 01814040 A CN01814040 A CN 01814040A CN 01814040 A CN01814040 A CN 01814040A CN 1446196 A CN1446196 A CN 1446196A
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- 239000000642 acaricide Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title description 30
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- -1 acyl group cyanide compound Chemical class 0.000 claims description 102
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 239000005864 Sulphur Substances 0.000 claims description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 230000000895 acaricidal effect Effects 0.000 claims description 5
- 230000003151 ovacidal effect Effects 0.000 abstract description 3
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- 241000238876 Acari Species 0.000 abstract 1
- 230000002506 adulticidal effect Effects 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
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- 150000001875 compounds Chemical class 0.000 description 75
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- 238000012360 testing method Methods 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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- 125000001309 chloro group Chemical group Cl* 0.000 description 20
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- 231100000208 phytotoxic Toxicity 0.000 description 5
- 230000000885 phytotoxic effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000003810 ethyl acetate extraction Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
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- 150000005826 halohydrocarbons Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 2
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- 102000013563 Acid Phosphatase Human genes 0.000 description 2
- 108010051457 Acid Phosphatase Proteins 0.000 description 2
- 240000002234 Allium sativum Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 1
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- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical group N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 239000005018 casein Substances 0.000 description 1
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- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
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- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 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
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000005911 methyl carbonate group Chemical class 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RCMHUQGSSVZPDG-UHFFFAOYSA-N phenoxybenzene;phosphoric acid Chemical compound OP(O)(O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 RCMHUQGSSVZPDG-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 244000161617 string bean plant Species 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical class [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000012056 up-stream process Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
化合物编号(2)-编号 | R1 | 性状 |
1 | -CO2CH3 | 粘性油 |
2 | -CO2CH2CH3 | 粘性油 |
3 | -CO2CH(CH3)2 | 粘性油 |
4 | -CO2C(CH3)3 | 粘性油 |
5 | -CO2CH2(CH2)4CH3 | 粘性油 |
6 | -CO2CH2C6H5 | 粘性油 |
7 | -CO2CH2CH=CH2 | 粘性油 |
8 | -CO2CH2C≡CH | 粘性油 |
9 | -CO2CH2CF3 | 粘性油 |
10 | -CO2CH2CH2OCH3 | 粘性油 |
11 | -CO2CH2CH2OC2H5 | 粘性油 |
12 | -CO2CH2CH2OCH2CH2CH3 | 粘性油 |
13 | -CO2CH2CH2OCH(CH3)2 | 粘性油 |
14 | -CO2CH2CH2OCH2(CH2)2CH3 | 粘性油 |
15 | -CO2CH2CH2OC(CH3)3 | 粘性油 |
16 | -CO2CH2CH2SCH3 | 粘性油 |
17 | -C(O)SCH3 | 粘性油 |
18 | -C(O)SC2H5 | 粘性油 |
19 | -C(O)SCH2CH2CH3 | 粘性油 |
20 | -C(O)SCH(CH3)2 | 粘性油 |
21 | -C(O)SCH2(CH2)2CH3 | 粘性油 |
22 | -C(O)SCH2(CH2)4CH3 | 粘性油 |
化合物编号(2)-编号 | 1H-NMR(CDCl3,ppm) |
1 | 1.32(s,9H),3.81(s,3H),4.71(s,1H),7.41(dd,4H) |
2 | 1.2-1.4(m,12H),4.25(q,2H),4.69(s,1H),7.41(dd,4H) |
3 | 1.2-1.4(m,15H),4.65(s,1H),5.0-5.1(m,1H),7.40(dd,4H) |
4 | 1.32(s,9H),1.46(s,9H),4.58(s,1H),7.35(d,2H),7.40(d,2H) |
5 | 0.8-0.9(m,3H),1.2-1.4(m,15H),1.6-1.7(m,2H),4.18(t,2H),4.69(s,1H),7.40(dd,4H) |
6 | 1.32(s,9H),4.73(s,1H),5.20(s,2H),7.2-7.5(m,9H) |
7 | 1.31(s,9H),4.67(dm,2H),4.73(s,1H),5.26(dd,1H),5.31(dd,1H),5.8-6.0(m,1H),7.38(d,2H),7.44(d,2H) |
8 | 1.32(s,9H),2.52(t,1H),4.75(s,1H),4.76(dd,2H),7.38(d,2H),7.44(d,2H) |
9 | 1.32(s,9H),4.5-4.6(m,2H),4.81(s,1H),7.38(d,2H),7.45(d,2H) |
10 | 1.32(s,9H),3.09(s,3H),3.6-3.65(m,2H),4.3-4.35(m,2H),4.75(s,1H),7.40(d,2H),7.41(d,2H) |
11 | 1.32(s,9H),1.15(t,3H),3.45(q,2H),3.7-3.75(m,2H),4.3-4.35(m,2H),4.74(s,1H),7.38(d,2H),7.40(d,2H) |
12 | 0.88(t,3H),1.33(s,9H),1.5-1.6(m,2H),3.36(t,2H),3.6-3.36(m,2H),4.3-4.35(m,2H),4.74(s,1H),7.38(d,2H),7.43(d,2H) |
13 | 1.08(d,3H),1.10(d,3H),1.31(s,9H),3.5-3.6(m,1H),3.6-3.65(m,2H),4.3-4.35(m,2H),4.74(s,1H),7.41(s,4H) |
14 | 0.91(t,3H),1.32(s,9H),1.3-1.4(m,2H),1.5-1.6(m,2H),3.40(t,2H),3.6-3.65(m,2H),4.3-4.35(m,2H),4.74(s,1H),7.38(d,2H),7.43(d,2H) |
15 | 1.12(s,9H),1.31(s,9H),3.5-3.55(m,2H),4.3-4.35(m,2H),4.73(s,1H),7.41(s,4H) |
16 | 1.32(s,9H),2.11(s,3H),2.73(t,2H),4.35(t,2H),4.73(s,1H),7.38(d,2H),7.44(d,2H) |
17 | 1.32(s,9H),2.44(s,3H),4.79(s,1H),7.46(d,2H),7.50(d,2H) |
18 | 1.26(t,3H),1.32(s,9H),2.91(q,2H),4.77(s,1H),7.38(d,2H),7.44(d,2H) |
19 | 0.95(t,3H),1.32(s,9H),1.5-1.7(m,2H),2.90(dt,2H),4.78(s,1H),7.37(d,2H),7.43(d,2H) |
20 | 1.3-1.4(m,15H),3.6-3.7(m,1H),4.73(s,1H),7.35(d,2H),7.43(d,2H) |
21 | 0.89(t,3H),1.3-1.4(m,2H),1.33(s,9H),1.5-1.6(m,2H),2.91(t,2H),4.77(s,1H),7.36(d,2H),7.43(d,2H) |
22 | 0.85(t,3H),1.32(s,9H),1.2-1.4(m,6H),1.5-1.6(m,2H),2.91(t,2H),4.77(s,1H),7.36(d,2H),7.43(d,2H) |
化合物编号 | Xm Yn R1 | 熔点(℃) |
1 | 4-C(CH3)3 2-CF3 -CO2CH3 | 137-139 |
2 | 4-C(CH3)3 2-CF3 -CO2C2H5 | 141-142 |
3 | 4-C(CH3)3 2-CF3 -CO2CH(CH3)2 | 141-142 |
4 | 4-C(CH3)3 2-CF3 -CO2C(CH3)3 | 137-138 |
5 | 4-C(CH3)3 2-CF3 -CO2CH2(CH2)4CH3 | 83-84 |
6 | 4-C(CH3)3 2-CF3 -CO2CH2C6H5 | 粘性油 |
7 | 4-C(CH3)3 2-CF3 -CO2CH2CH=CH2 | 107-108 |
8 | 4-C(CH3)3 2-CF3 -CO2CH2C≡CH | 106-108 |
9 | 4-C(CH3)3 2-CF3 -CO2CH2CF3 | 94-95 |
10 | 4-C(CH3)3 2-CF3 -CO2CH2CH2OCH3 | 73-74 |
11 | 4-C(CH3)3 2-CF3 -CO2CH2CH2OC2H5 | 粘性油 |
12 | 4-C(CH3)3 2-CF3 -CO2CH2CH2OCH2CH2CH3 | 粘性油 |
13 | 4-C(CH3)3 2-CF3 -CO2CH2CH2OCH(CH3)2 | 粘性油 |
14 | 4-C(CH3)3 2-CF3 -CO2CH2CH2OCH2(CH2)2CH3 | 粘性油 |
15 | 4-C(CH3)3 2-CF3 -CO2CH2CH2OC(CH3)3 | 粘性油 |
16 | 4-C(CH3)3 2-CF3 -CO2CH2CH2SCH3 | 粘性油 |
17 | 4-C(CH3)3 2-CF3 -C(O)SCH3 | 113-116 |
18 | 4-C(CH3)3 2-CF3 -C(O)SC2H5 | 113-114 |
19 | 4-C(CH3)3 2-CF3 -C(O)SCH2CH2CH3 | 85-87 |
20 | 4-C(CH3)3 2-CF3 -C(O)SCH(CH3)2 | 81-84 |
21 | 4-C(CH3)3 2-CF3 -C(O)SCH2(CH2)2CH3 | 粘性油 |
22 | 4-C(CH3)3 2-CF3 -C(O)SCH2(CH2)4CH3 | 粘性油 |
23 | 2-Cl 2-CF3 -CO2C2H5 | 71-73 |
24 | 3-Cl 2-CF3 -CO2C2H5 | 89-92 |
25 | 4-Cl 2-CF3 -CO2C2H5 | 粘性油 |
26 | 2,4-Cl2 2-CF3 -CO2C2H5 | 70-72 |
27 | 2,6-Cl2 2-CF3 -CO2C2H5 | 132-134 |
28 | 3,4-Cl2 2-CF3 -CO2C2H5 | 66-68 |
29 | 3,5-Cl2 2-CF3 -CO2C2H5 | 123-124 |
30 | 4-Cl 2-CF3 -CO2CH3 | 89-92 |
31 | 4-Cl 2-CF3 -CO2CH2CH2CH3 | 60-62 |
32 | 4-Cl 2-CF3 -CO2CH(CH3)2 | 粘性油 |
33 | 4-Cl 2-CF3 -CO2CH2(CH2)2CH3 | 42-43 |
34 | 4-Cl 2-CF3 -CO2C(CH2)3 | 94-97 |
35 | 4-Cl 2-CF3 -CO2CH2CH(CH3)2 | 94-96 |
化合物编号 | Xm Yn R1 | 熔点(℃) |
36 | 4-C(CH3)3 2-CF3, -CO2C2H54-F | 111-112 |
37 | 4-C(CH3)3 2-CF3, -CO2C2H55-F | 110-112 |
38 | 4-C(CH3)3 2-CF3, -CO2C2H56-F | 粘性油 |
39 | 4-Cl 2-Cl -CO2C2H5 | 粘性油 |
40 | 4-Cl 2-F -CO2CH3 | 59-60 |
41 | 4-Cl 2-Br -CO2CH3 | 粘性油 |
42 | 4-Cl 2-CH3 -CO2CH3 | 65-68 |
43 | 4-Cl 2,6-F2 -CO2CH3 | 粘性油 |
44 | 4-F 2-CF3 -CO2C2H5 | 75-76 |
45 | 4-Br 2-CF3 -CO2C2H5 | 43-45 |
46 | 4-CH3 2-CF3 -CO2C2H5 | 57-58 |
47 | 4-CF3 2-CF3 -CO2C2H5 | 粘性油 |
48 | 4-CH(CH3)2 2-CF3 -CO2C2H5 | 79-80 |
49 | 4-CH2CH(CH3)2 2-CF3 -CO2C2H5 | 38-40 |
化合物编号 | 1H-NMR(CDCl3,ppm) |
1 | 1.35(s,9H),3.92(s,3H),7.07(d,1H),7.4-7.7(m,6H),7.78(d,1H) |
2 | 1.34(t,3H),1.35(s,9H),4.2-4.5(m,2H),7.07(d,1H),7.4-7.5(m,3H),7.5-7.6(m,3H),7.78(d,1H) |
3 | 1.2-1.4(m,15H),5.1-5.2(m,1H),7.08(d,1H),7.4-7.6(m,6H),7.79(d,1H) |
4 | 1.35(s,9H),1.52(s,9H),7.05(d,1H),7.4-7.6(m,6H),7.77(d,1H) |
5 | 0.8-1.0(m,3H),1.2-1.4(m,15H),1.6-1.8(m,2H),4.2-4.4(m,2H),7.07(d,1H),7.4-7.6(m,6H),7.78(d,1H) |
6 | 1.34(s,9H),5.3-5.4(m,2H),7.04(d,1H),7.3-7.6(m,11H),7.75(d,1H) |
7 | 1.35(s,9H),4.7-4.9(m,2H),5.30(dd,1H),5.38(dd,1H),5.9-6.0(m,1H),7.07(d,1H),7.4-7.7(m,6H),7.78(d,1H) |
8 | 1.34(s 9H),2.55(t,1H),4.87(d,2H),7.10(d,1H),7.4-7.6(m,6H),7.77(d,1H) |
9 | 1.36(s,9H),4.6-4.8(m,2H),6.98(d,1H),7.4-7.7(m,6H),7.80(d,1H) |
10 | 1.35(s,9H),3.36(s,3H),3.6-3.65(m,2H),4.4-4.5(m,2H),7.14(d,1H),7.4-7.6(m,6H),7.78(d,1H) |
11 | 1.17(t,3H),1.34(s,9H),3.50(q,2H),3.6-3.7(m,2H),4.4-4.5(m,2H),7.15(d,1H),7.4-7.6(m,6H),7.80(d,1H) |
12 | 0.89(t,3H),1.34(s,9H),1.5-1.6(m,2H),3.40(t,2H),3.65-3.7(m,2H),4.4-4.5(m,2H),7.15(d,1H),7.4-7.6(m,6H),7.79(d,1H) |
13 | 1.1-1.2(m,6H),1.34(s,9H),3.5-3.6(m,1H),3.6-3.65(m,2H),4.3-4.35(m,2H),7.14(d,1H),7.4-7.6(m,6H),7.77(d,1H) |
14 | 0.90(t,3H),1.34(s,9H),1.3-1.4(m,2H),1.5-1.6(m,2H),3.44(t,2H),3.6-3.7(m,2H),4.4-4.5(m,2H),7.15(d,1H),7.4-7.6(m,6H),7.77(d,1H) |
15 | 1.16(s,9H),1.34(s,9H),3.6-3.65(m,2H),4.4-4.45(m,2H),7.17(d,1H),7.4-7.6(m,6H),7.76(d,1H) |
16 | 1.35(s,9H),2.14(s,3H),2.77(t,2H),4.4-4.6(m,2H),7.08(d,1H), 7.4-7.6(m,6H),7.77(d,1H) |
17 | 1.35(t,3H),2.42(s,3H),7.19(d,1H),7.5-7.65(m,6H),7.77(d,1H) |
18 | 1.29(t,3H),1.35(s,9H),2.99(qd,2H),7.21(d,1H),7.4-7.6(m,6H),7.76(d,1H) |
19 | 0.97(t,3H),1.35(s,9H),1.5-1.7(m,2H),2.8-3.1(m,2H),7.22(d,1H),7.4-7.7(m,6H),7.76(d,1H) |
20 | 1.2-1.4(m,15H),3.6-3.8(m,1H),7.23(d,1H),7.4-7.7(m,6H),7.76(d,1H) |
21 | 0.91(t,3H),1.3-1.4(m,2H),1.35(s,9H),1.5-1.6(m,2H),2.9-3.1(m,2H),7.22(d,1H),7.4-7.6(m,6H),7.76(d,1H) |
22 | 0.87(t,3H),1.2-1.4(m,6H),1.35(s,9H),1.5-1.7(m,2H),2.9-3.1(m,2H),7.22(d,1H),7.4-7.6(m,6H),7.76(d,1H) |
23 | 1.28(t,3H),4.15(q,2H),7.3-7.4(m,2H),7.4-7.5(m,2H),7.7-7.9(m,3H),8.2-8.3(m,1H) |
24 | 1.34(t,3H),4.3-4.5(m,2H),7.14(d,1H),7.4-7.7(m,6H),7.80(d,1H) |
25 | 1.34(t,3H),4.3-4.5(m,2H),7.12(d,1H),7.4-7.8(m,6H),7.79(d,1H) |
26 | 1.30(t,3H),4.18(q,2H),7.30(dd,1H),7.40(d,1H),7.49(d,1H),7.7-7.8(m,2H),7.8-7.9(m,1H),8.2-8.3(m,1H) |
化合物编号 | 1H-NMR(CDCl3,ppm) |
27 | 1.28(t,3H),4.19(q,2H),7.28(d,1H),7.39(s,1H),7.42(d,1H),7.7-7.8(m,2H),7.8-7.9m,1H),8.2-8.3(m,1H) |
28 | 1.34(t,3H),4.3-4.5(m,2H),7.19(d,1H),7.5-7.9(m,6H) |
29 | 1.35(t,3H),4.3-4.5(m,2H),7.21(d,1H),7.50(d,1H),7.5-7.7(m,4H),7.81(d,1H) |
30 | 3.93(s,3H),7.12(d,1H),7.4-7.5(m,3H),7.6-7.7(m,3H),7.80(d,1H) |
31 | 0.96(t,3H),1.6-1.8(m,2H),4.2-4.4(m,2H),7.11(d,1H),7.4-7.5(m,3H),7.6-7.7(m,3H),7.79(d,1H) |
32 | 1.28(d,3H),1.34(d,3H),5.1-5.2(m,2H),7.13(d,1H),7.4-7.5(m,3H),7.6-7.7(m,3H),7.89(d,1H) |
33 | 0.93(t,3H),1.3-1.5(m,2H),1.6-1.8(m,2H),4.2-4.4(m,2H),7.10(d,1H),7.4-7.6(m,3H),7.6-7.7(m,3H),7.62(d,1H) |
34 | 1.51(s,9H),7.13(d,1H),7.3-7.7(m,6H),7.79(d,1H) |
35 | 0.95(d,6H),1.9-2.1(m,1H),4.0-4.2(m,2H),7.10(d,1H),7.4-7.5(m,3H),7.6-7.7(m,3H),7.62(d,1H) |
36 | 1.3-1.4(m,12H),4.2-4.5(m,2H),7.1-7.2(m,2H),7.4-7.6(m,5H) |
37 | 1.3-1.4(m,12H),4.2-4.5(m,2H),6.65(m,1H),7.2-7.3(m,1H),7.4-7.6(m,4H),7.7-7.8(m,1H) |
38 | 1.3-1.4(m,12H),4.2-4.5(m,2H),7.3-7.4(m,1H),7.45(d,1H),7.5-7.7(m,4H) |
39 | 1.33(t,3H),4.2-4.5(m,2H),7.1-7.2(m,2H),7.3-7.4(m,4H),7.5-7.6(m,2H) |
40 | 3.91(s,3H),7.20(dd,1H),7.2-7.5(m,5H),7.6-7.7(m,1H),7.8-7.9(m,1H) |
41 | 3.93(s,3H),7.17(d,1H),7.3-7.4(m,2H),7.4-7.5(m,2H),7.6-7.7(m,3H) |
42 | 2.48(s,3H),3.91(s,3H),7.10(t,1H),7.3-7.5(m,6H),7.56(dd,1H) |
43 | 3.93(s,3H),6.9-7.1(m,2H),7.4-7.6(m,5H) |
44 | 1.34(t,3H),4.3-4.5(m,2H),7.10(d,1H),7.1-7.2(m,2H),7.50(t,1H),7.6-7.8(m,3H),7.79(d,1H) |
45 | 1.34(t,3H),4.3-4.5(m,2H),7.12(d,1H),7.5-7.7(m,6H),7.79(d,1H) |
46 | 1.34(t,3H),2.41(s,3H),4.3-4.5(m,2H),7.04(d,1H),7.2-7.3(m,2H),7.45(t,1H),7.5-7.6(m,3H),7.77(d,1H) |
47 | 1.34(t,3H),4.3-4.5(m,2H),7.17(d,1H),7.53(t,1H),7.6-7.8(m,6H) |
48 | 1.28(d,6H),1.34(t,3H),2.9-3.1(m,1H),4.2-4.5(m,2H),7.06(d,1H),7.34(d,2H),7.46(t,1H),7.5-7.7(m,3H),7.78(d,1H) |
49 | 0.91(d,6H),1.34(t,3H),1.8-2.0(m,1H),2.52(d,2H),4.3-4.5(m,2H),7.02(d,1H),7.26(d,2H),7.43(t,1H),7.5-7.6(m,3H),7.77(d,1H) |
调整的死亡率(%) | ||
喷洒3天后 | 喷洒5天后 | |
试验化合物A | 100 | 95 |
试验化合物B | 100 | 93 |
试验化合物C | 100 | 100 |
试验化合物E | 48 | 0 |
植物毒性 | |||||
农作物(品种) | 稀释倍数 | 喷雾后的天数 | 试验化合物A | 试验化合物B | 试验化合物C |
柑桔(酸橙) | 400 | 40 | - | 无 | - |
柑桔(温州蜜柑) | 1000 | 40 | - | 无 | - |
柑桔(伊予(iyo)) | 1000 | 40 | 无 | 无 | 无 |
苹果(富士) | 1000 | 27 | 无 | 无 | 无 |
苹果(乔纳金(jonagold)) | 1000 | 14 | 无 | 无 | 无 |
茶(薮北(yabukita)) | 1000 | 21 | 无 | 无 | 无 |
梨(丰水(hosui)) | 2000 | 21 | 无 | 无 | 无 |
葡萄(皮奥奈(pione)) | 2000 | 18 | 无 | 无 | 无 |
茄子(千雨(senryo)) | 1000 | 14 | - | 无 | - |
Claims (15)
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JP2000379844A JP3572483B2 (ja) | 2000-08-11 | 2000-12-14 | アシルアセトニトリル化合物、その製造方法及び該化合物を含有する殺ダニ剤 |
JP379844/2000 | 2000-12-14 |
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US (1) | US6899886B2 (zh) |
EP (1) | EP1308437B1 (zh) |
JP (1) | JP3572483B2 (zh) |
KR (1) | KR100544363B1 (zh) |
CN (1) | CN1193983C (zh) |
AU (1) | AU2001277730B8 (zh) |
BR (1) | BR0113180B1 (zh) |
CA (1) | CA2418770C (zh) |
DE (1) | DE60131663D1 (zh) |
ES (1) | ES2296776T3 (zh) |
HK (1) | HK1059254A1 (zh) |
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WO (1) | WO2002014263A1 (zh) |
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EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
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JPS6011452A (ja) | 1983-06-30 | 1985-01-21 | Showa Denko Kk | α−シアノケトン類誘導体及び除草剤 |
JPS6011401A (ja) | 1983-06-30 | 1985-01-21 | Showa Denko Kk | α−シアノケトン類誘導体を有効成分として含有する農園芸用殺菌剤 |
JPH0543518A (ja) | 1991-08-13 | 1993-02-23 | Hokko Chem Ind Co Ltd | ハロアルキルフエニルケトン誘導体および種子消毒剤 |
TW513285B (en) * | 1997-02-14 | 2002-12-11 | Ishihara Sangyo Kaisha | Acrylonitrile compounds, process and intermediates for their production, method for controlling pests comprising using them and pesticides, fungicides and marine antifouling agents containing them |
IL147660A0 (en) | 1999-07-30 | 2002-08-14 | Ishihara Sangyo Kaisha | Geometrical isomer of acrylonitrile compound, mixture thereof, and process for producing these |
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CN102405914A (zh) * | 2011-11-21 | 2012-04-11 | 广东中迅农科股份有限公司 | 一种含有丁氟螨酯和四螨嗪的增效杀螨组合物 |
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CN110551148A (zh) * | 2019-05-17 | 2019-12-10 | 华东理工大学 | 含硅酰基乙腈化合物及其制备方法与应用 |
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Also Published As
Publication number | Publication date |
---|---|
CN1193983C (zh) | 2005-03-23 |
US6899886B2 (en) | 2005-05-31 |
TW591008B (en) | 2004-06-11 |
HK1059254A1 (en) | 2004-06-25 |
AU7773001A (en) | 2002-02-25 |
AU2001277730B8 (en) | 2007-05-24 |
JP2002121181A (ja) | 2002-04-23 |
JP3572483B2 (ja) | 2004-10-06 |
CA2418770A1 (en) | 2003-02-10 |
KR100544363B1 (ko) | 2006-01-23 |
KR20030029815A (ko) | 2003-04-16 |
CA2418770C (en) | 2008-03-25 |
ES2296776T3 (es) | 2008-05-01 |
WO2002014263A1 (fr) | 2002-02-21 |
EP1308437B1 (en) | 2007-11-28 |
AU2001277730B2 (en) | 2007-03-15 |
DE60131663D1 (de) | 2008-01-10 |
EP1308437A4 (en) | 2004-12-15 |
BR0113180B1 (pt) | 2015-01-06 |
US20030208086A1 (en) | 2003-11-06 |
EP1308437A1 (en) | 2003-05-07 |
BR0113180A (pt) | 2003-07-08 |
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