CN102395566A - 吡唑基丙烯腈类化合物及其应用 - Google Patents
吡唑基丙烯腈类化合物及其应用 Download PDFInfo
- Publication number
- CN102395566A CN102395566A CN2010800163776A CN201080016377A CN102395566A CN 102395566 A CN102395566 A CN 102395566A CN 2010800163776 A CN2010800163776 A CN 2010800163776A CN 201080016377 A CN201080016377 A CN 201080016377A CN 102395566 A CN102395566 A CN 102395566A
- Authority
- CN
- China
- Prior art keywords
- compound
- protective embankment
- milliliters
- methyl
- carbonyl
- 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
- QNIXGXJJMCELJA-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)prop-2-enenitrile Chemical class N#CC(=C)C=1C=CNN=1 QNIXGXJJMCELJA-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 47
- -1 alkenyl oxygen Chemical compound 0.000 claims abstract description 20
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 12
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 230000001681 protective effect Effects 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 11
- 241000238631 Hexapoda Species 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 238000006243 chemical reaction Methods 0.000 description 62
- 239000003921 oil Substances 0.000 description 50
- 239000000243 solution Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000002585 base Substances 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 10
- 238000010792 warming Methods 0.000 description 10
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 102000002322 Egg Proteins Human genes 0.000 description 6
- 108010000912 Egg Proteins Proteins 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 210000004681 ovum Anatomy 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 4
- FSWUGFSHWYDKTO-UHFFFAOYSA-N 1-ethyl-3-methylpyrazole Chemical compound CCN1C=CC(C)=N1 FSWUGFSHWYDKTO-UHFFFAOYSA-N 0.000 description 4
- 241000272639 Brachycaudus mimeuri Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940127007 Compound 39 Drugs 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- APJLTUBHYCOZJI-VZCXRCSSSA-N cyenopyrafen Chemical compound CC1=NN(C)C(\C(OC(=O)C(C)(C)C)=C(/C#N)C=2C=CC(=CC=2)C(C)(C)C)=C1C APJLTUBHYCOZJI-VZCXRCSSSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QYVRRKWAJJONJU-UHFFFAOYSA-N 1-ethyl-3,4-dimethylpyrazole Chemical compound CCN1C=C(C)C(C)=N1 QYVRRKWAJJONJU-UHFFFAOYSA-N 0.000 description 2
- KAFYYOLFAOPWEI-UHFFFAOYSA-N 2-(1-ethylpyrazol-3-yl)prop-2-enenitrile Chemical class CCN1C=CC(C(=C)C#N)=N1 KAFYYOLFAOPWEI-UHFFFAOYSA-N 0.000 description 2
- OFPLNBAFXLMBEM-UHFFFAOYSA-N 4-fluoro-5-methyl-1h-pyrazole Chemical class CC1=NNC=C1F OFPLNBAFXLMBEM-UHFFFAOYSA-N 0.000 description 2
- SHDMYGCRVXWTGR-UHFFFAOYSA-N 4-iodo-5-methyl-1h-pyrazole Chemical class CC=1NN=CC=1I SHDMYGCRVXWTGR-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241001498622 Cixius wagneri Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000578422 Graphosoma lineatum Species 0.000 description 2
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical class CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000545442 Radix Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical class CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical class CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical class CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical class CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical class CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical class CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical class CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241000059559 Agriotes sordidus Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000927584 Frankliniella occidentalis Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
- 241000661348 Leptocorisa acuta Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000409991 Mythimna separata Species 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- 241000084931 Neohydatothrips variabilis Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000167882 Rhopalosiphum maidis Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 102000013275 Somatomedins Human genes 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012363 selectfluor Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
Abstract
Description
Claims (6)
- 权 利 要 求 书1、 一种吡唑基丙烯腈类化合物, 如通式 I所示:式中:Ri选自 H、 d-C4烷氧基 d-C2垸基、 C3-C5烯基氧 d-C2垸基、 C3-C5炔基氧 d-C2垸 基、 C C4垸硫基 d-C2垸基、 d-C5烷基羰基、 C3-C8环垸基羰基、 d-C5垸氧基羰基或 d-C5R2选自 C1或甲基;R3选自 H、 甲基、 CN、 N02或卤素;或其立体异构体。
- 2、 按照权利要求 1所述的化合物, 其特征在于, 通式 I中:选自 H、 CrC4烷氧基 CrC2垸基、 d-C5垸基羰基、 C3-C3环垸基羰基或 d-C5垸氧R2选自甲基;选自 H、 甲基、 CN或卤素;或其立体异构体。
- 3、 按照权利要求 2所述的化合物, 其特征在于, 通式 I中:选自 C C2垸氧基甲基、 C4-C5垸基羰基、 C3-C5环烷基羰基或 d-C2垸氧基羰基;R2选自甲基;R3选自 H、 CN、 F或 CI;或其立体异构体。
- 4、 一种按照权利要求 1所述的通式 I化合物控制螨害、 虫害的用途。
- 5、 一种杀虫、 杀螨组合物, 含有如权利要求 1所述的通式 I所示化合物为活性组分 和农业、 林业或卫生上可接受的载体, 组合物中活性组分的重量百分含量为 1-99%。
- 6、 一种防治虫害、 螨害的方法, 其特征在于: 将权利要求 5所述的杀虫、 杀螨组合 物以每公顷 10克到 1000克的有效剂量施于需要控制的害虫、 害螨或其生长的介质上。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010800163776A CN102395566B (zh) | 2009-04-29 | 2010-04-27 | 吡唑基丙烯腈类化合物及其应用 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200910083205XA CN101875633B (zh) | 2009-04-29 | 2009-04-29 | 吡唑基丙烯腈类化合物及其应用 |
CN200910083205.X | 2009-04-29 | ||
CN2010800163776A CN102395566B (zh) | 2009-04-29 | 2010-04-27 | 吡唑基丙烯腈类化合物及其应用 |
PCT/CN2010/072224 WO2010124617A1 (zh) | 2009-04-29 | 2010-04-27 | 吡唑基丙烯腈类化合物及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102395566A true CN102395566A (zh) | 2012-03-28 |
CN102395566B CN102395566B (zh) | 2013-12-25 |
Family
ID=43018327
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910083205XA Active CN101875633B (zh) | 2009-04-29 | 2009-04-29 | 吡唑基丙烯腈类化合物及其应用 |
CN2010800163776A Active CN102395566B (zh) | 2009-04-29 | 2010-04-27 | 吡唑基丙烯腈类化合物及其应用 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910083205XA Active CN101875633B (zh) | 2009-04-29 | 2009-04-29 | 吡唑基丙烯腈类化合物及其应用 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8455532B2 (zh) |
EP (1) | EP2426110B1 (zh) |
JP (1) | JP5524328B2 (zh) |
CN (2) | CN101875633B (zh) |
BR (1) | BRPI1011970B1 (zh) |
ES (1) | ES2441556T3 (zh) |
WO (1) | WO2010124617A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107743976A (zh) * | 2013-11-26 | 2018-03-02 | 沈阳中化农药化工研发有限公司 | 杀虫杀螨组合物 |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CN102898373B (zh) * | 2011-07-25 | 2014-12-10 | 中国中化股份有限公司 | Z-3-酰氧基-3-(1-乙基吡唑基)丙烯腈类化合物的制备方法 |
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 |
CN104663702B (zh) * | 2013-11-26 | 2018-01-16 | 沈阳中化农药化工研发有限公司 | 一种含有菊酯类杀虫剂的杀虫杀螨组合物 |
CN104663670B (zh) * | 2013-11-26 | 2017-12-19 | 沈阳中化农药化工研发有限公司 | 一种协同杀螨组合物 |
CN104663688B (zh) * | 2013-11-26 | 2017-12-26 | 沈阳中化农药化工研发有限公司 | 一种含有联苯肼酯的杀虫杀螨组合物 |
CN104663668B (zh) * | 2013-11-26 | 2017-12-19 | 沈阳中化农药化工研发有限公司 | 一种含有乙酰辅酶a抑制剂类杀虫剂的杀虫杀螨组合物 |
CN104663687B (zh) * | 2013-11-26 | 2017-12-19 | 沈阳中化农药化工研发有限公司 | 一种含有氨基甲酸酯类杀虫剂的杀虫杀螨组合物 |
CN104663692B (zh) * | 2013-11-26 | 2018-01-16 | 沈阳中化农药化工研发有限公司 | 一种含有昆虫生长调节剂类杀虫剂的杀虫杀螨组合物 |
CN104663679B (zh) * | 2013-11-26 | 2017-12-19 | 沈阳中化农药化工研发有限公司 | 一种含有大环内酯类杀虫剂的杀虫杀螨组合物 |
CN104663704B (zh) * | 2013-11-26 | 2017-12-19 | 沈阳中化农药化工研发有限公司 | 一种含有atp合成酶抑制剂类杀螨剂的杀虫杀螨组合物 |
CN104663666B (zh) * | 2013-11-26 | 2017-10-20 | 沈阳中化农药化工研发有限公司 | 一种含有线粒体电子传递抑制剂类杀螨剂的杀虫杀螨组合物 |
CN104663672B (zh) * | 2013-11-26 | 2018-01-02 | 沈阳中化农药化工研发有限公司 | 一种含有螨虫生长抑制剂类杀螨剂的杀虫杀螨组合物 |
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 |
CN109221155A (zh) * | 2014-12-25 | 2019-01-18 | 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 |
CN105801484B (zh) * | 2014-12-29 | 2018-08-07 | 沈阳中化农药化工研发有限公司 | 一种吡唑基丙烯腈类化合物的制备方法 |
CN106305727B (zh) * | 2015-06-18 | 2019-02-15 | 沈阳中化农药化工研发有限公司 | 一种含有增效剂的杀虫杀螨组合物 |
CN106305732B (zh) * | 2015-06-18 | 2019-03-19 | 沈阳中化农药化工研发有限公司 | 一种含有氟螨嗪的杀虫杀螨组合物 |
CN105394044A (zh) * | 2015-12-31 | 2016-03-16 | 青岛瀚生生物科技股份有限公司 | 一种杀螨组合物及其应用 |
CN106818808A (zh) * | 2017-02-15 | 2017-06-13 | 海南省植物保护总站(海南省农药检定所) | 含有乙唑螨腈和丁醚脲的杀虫组合物 |
CN106719687A (zh) * | 2017-02-16 | 2017-05-31 | 佛山市瑞生通科技有限公司 | 一种含乙唑螨腈和丁氟螨酯的农药组合物 |
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 |
CN108684681B (zh) * | 2017-03-31 | 2021-03-30 | 沈阳中化农药化工研发有限公司 | 一种杀螨制剂及其应用 |
CN109566628B (zh) * | 2017-09-28 | 2021-04-02 | 沈阳中化农药化工研发有限公司 | 一种杀螨组合物及其应用 |
CN109832283A (zh) * | 2017-11-29 | 2019-06-04 | 江苏龙灯化学有限公司 | 一种杀螨组合物 |
CN109832279A (zh) * | 2017-11-29 | 2019-06-04 | 江苏龙灯化学有限公司 | 一种杀虫组合物 |
CN110003111B (zh) * | 2018-01-04 | 2020-11-13 | 浙江省化工研究院有限公司 | 一种2-芳基-3-醚基-3-吡唑丙烯腈类化合物的制备方法 |
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 |
CN111771891A (zh) * | 2019-04-04 | 2020-10-16 | 浙江省化工研究院有限公司 | 一种含唑醚螨腈和菊酯类农药的杀螨组合物 |
CN111789122A (zh) * | 2019-04-09 | 2020-10-20 | 浙江省化工研究院有限公司 | 一种含唑醚螨腈和螺环季酮酸类农药的杀螨组合物 |
CN113372374B (zh) * | 2021-01-20 | 2023-03-28 | 华中师范大学 | 一种丙烯腈类化合物及其制备方法和应用、一种杀虫剂、一种杀螨剂 |
EP4294185A1 (en) | 2021-02-19 | 2023-12-27 | Syngenta Crop Protection AG | Insect and acarina pest control |
US20240138409A1 (en) | 2021-02-19 | 2024-05-02 | Syngenta Crop Protection Ag | Insect and acarina pest control |
WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023280999A1 (en) | 2021-07-07 | 2023-01-12 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
CN117998986A (zh) | 2021-09-23 | 2024-05-07 | 先正达农作物保护股份公司 | 昆虫、蜱螨目和线虫类有害生物控制 |
WO2023105065A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
CN114369063B (zh) * | 2022-01-24 | 2023-09-26 | 沈阳农业大学 | 一种吡唑基丙烯腈类化合物及其制备方法和应用 |
WO2023152340A1 (en) | 2022-02-10 | 2023-08-17 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003206281A (ja) * | 2002-01-10 | 2003-07-22 | Nissan Chem Ind Ltd | アクリロニトリル化合物 |
CN1763003A (zh) * | 1996-04-25 | 2006-04-26 | 日产化学工业株式会社 | 乙烯衍生物和含有该衍生物的杀有害生物剂 |
CN101367784A (zh) * | 2008-09-28 | 2009-02-18 | 江苏省农药研究所股份有限公司 | 丙烯腈类化合物及其制备方法和应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1227229C (zh) * | 1996-04-25 | 2005-11-16 | 日产化学工业株式会社 | 乙烯衍生物和含有该衍生物的杀有害生物剂 |
JP2000119256A (ja) * | 1998-10-14 | 2000-04-25 | Nissan Chem Ind Ltd | アクリロニトリル化合物 |
JP4609610B2 (ja) | 2000-06-05 | 2011-01-12 | 日産化学工業株式会社 | 4−メチルピラゾール−5−カルボン酸化合物の製造方法 |
JP2003201280A (ja) * | 2001-10-24 | 2003-07-18 | Nissan Chem Ind Ltd | アクリロニトリル化合物 |
JP2003206280A (ja) | 2001-12-28 | 2003-07-22 | Takeda Chem Ind Ltd | ビアリール化合物およびその用途 |
CN100432058C (zh) | 2003-12-12 | 2008-11-12 | 沈阳化工研究院 | 具有杀菌活性的α-(吡唑甲酸基)乙酰苯胺类化合物 |
-
2009
- 2009-04-29 CN CN200910083205XA patent/CN101875633B/zh active Active
-
2010
- 2010-04-27 ES ES10769306.1T patent/ES2441556T3/es active Active
- 2010-04-27 BR BRPI1011970A patent/BRPI1011970B1/pt active IP Right Grant
- 2010-04-27 CN CN2010800163776A patent/CN102395566B/zh active Active
- 2010-04-27 EP EP10769306.1A patent/EP2426110B1/en active Active
- 2010-04-27 JP JP2012507591A patent/JP5524328B2/ja active Active
- 2010-04-27 WO PCT/CN2010/072224 patent/WO2010124617A1/zh active Application Filing
- 2010-04-27 US US13/265,010 patent/US8455532B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1763003A (zh) * | 1996-04-25 | 2006-04-26 | 日产化学工业株式会社 | 乙烯衍生物和含有该衍生物的杀有害生物剂 |
JP2003206281A (ja) * | 2002-01-10 | 2003-07-22 | Nissan Chem Ind Ltd | アクリロニトリル化合物 |
CN101367784A (zh) * | 2008-09-28 | 2009-02-18 | 江苏省农药研究所股份有限公司 | 丙烯腈类化合物及其制备方法和应用 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107743976A (zh) * | 2013-11-26 | 2018-03-02 | 沈阳中化农药化工研发有限公司 | 杀虫杀螨组合物 |
CN107743976B (zh) * | 2013-11-26 | 2020-05-08 | 沈阳中化农药化工研发有限公司 | 杀虫杀螨组合物 |
Also Published As
Publication number | Publication date |
---|---|
JP2012525340A (ja) | 2012-10-22 |
BRPI1011970B1 (pt) | 2017-04-04 |
CN101875633A (zh) | 2010-11-03 |
JP5524328B2 (ja) | 2014-06-18 |
ES2441556T3 (es) | 2014-02-05 |
CN101875633B (zh) | 2012-01-18 |
EP2426110B1 (en) | 2013-10-16 |
CN102395566B (zh) | 2013-12-25 |
EP2426110A1 (en) | 2012-03-07 |
WO2010124617A1 (zh) | 2010-11-04 |
BRPI1011970A2 (pt) | 2015-09-22 |
US8455532B2 (en) | 2013-06-04 |
EP2426110A4 (en) | 2012-10-31 |
US20120035236A1 (en) | 2012-02-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102395566A (zh) | 吡唑基丙烯腈类化合物及其应用 | |
Zhang et al. | Design, syntheses and 3D-QSAR studies of novel N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol-2-ones as protoporphyrinogen oxidase inhibitors | |
CN104649973B (zh) | 一种吡唑酰胺类化合物及其用途 | |
CN101279950A (zh) | 2-嘧啶氧(硫)基苯甲酸基乙酰胺类化合物及其应用 | |
CN101367784B (zh) | 丙烯腈类化合物及其制备方法和应用 | |
CN106187893B (zh) | 一种吡唑酰胺类化合物及其用途 | |
CN103833639A (zh) | 吡唑基丙烯腈类化合物及其应用 | |
CN105732587B (zh) | 6-取代嘧啶基喹唑啉酮类化合物及其用途 | |
CN104557742A (zh) | 一种丙硫菌唑类似物的制备方法 | |
CN104649997B (zh) | 一种2, 4‑二甲基噻唑基丙烯腈类化合物及其应用 | |
CN103833744B (zh) | 1‑乙基吡唑基丙烯腈类化合物及其应用 | |
CN106431977B (zh) | 一种不饱和肟醚类化合物及其用途 | |
CN104650063B (zh) | 一种2,4‑二甲基恶唑基丙烯腈类化合物及其应用 | |
CN106831618B (zh) | 一种季铵盐类化合物及其应用 | |
CN111285815A (zh) | 一种吡嗪酰胺类化合物及用途 | |
CN105418590B (zh) | 6-取代吡唑基喹唑啉酮类化合物及其用途 | |
CN103833668B (zh) | 邻三氟甲基苯基丙烯腈类化合物及其应用 | |
CN103833638B (zh) | 苯基吡唑基丙烯腈类化合物及其应用 | |
CN113045562B (zh) | 一种用于植物抑菌的噻唑化合物及其用途 | |
CN101407490B (zh) | 3-苯甲酸基丙烯酸酯类化合物及其应用 | |
CN1927811B (zh) | 一种4-苯甲酸基丁烯酸酯类化合物及其应用 | |
CN103833669A (zh) | 噻唑基丙烯腈类化合物及其应用 | |
CN103833743A (zh) | 噻唑基吡唑基丙烯腈类化合物及其应用 | |
CN103833670A (zh) | 2-氯噻唑基丙烯腈类化合物及其应用 | |
CN103833742A (zh) | 吡唑基噻唑基丙烯腈类化合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160127 Address after: 110021 Liaodong Road, Tiexi District, Liaoning, No. 8-1, No. Patentee after: SHENYANG SINOCHEM PESTICIDE CHEMICAL RESEARCH AND DEVELOPMENT CO., LTD. Address before: 100031 Beijing, Xicheng District, the door of the revitalization of the main street, No. 28 Patentee before: SINOCHEM Corp. Patentee before: Shenyang Research Institute of Chemical Industry |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20120328 Assignee: ZHONGHUA CROP PROTECTOR Co.,Ltd. Assignor: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd. Contract record no.: X2020210000034 Denomination of invention: Pyrazolyl acrylonitrile compounds and their applications Granted publication date: 20131225 License type: Common License Record date: 20201217 |
|
EC01 | Cancellation of recordation of patent licensing contract | ||
EC01 | Cancellation of recordation of patent licensing contract |
Assignee: ZHONGHUA CROP PROTECTOR CO.,LTD. Assignor: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd. Contract record no.: X2020210000034 Date of cancellation: 20220617 |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20120328 Assignee: ZHONGHUA CROP PROTECTOR CO.,LTD. Assignor: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd. Contract record no.: X2022210000020 Denomination of invention: Pyrazolyl acrylonitrile compounds and their applications Granted publication date: 20131225 License type: Common License Record date: 20220620 |