DE69519127T2 - Inzektizide Tetrahydrofuranverbindung - Google Patents
Inzektizide TetrahydrofuranverbindungInfo
- Publication number
- DE69519127T2 DE69519127T2 DE69519127T DE69519127T DE69519127T2 DE 69519127 T2 DE69519127 T2 DE 69519127T2 DE 69519127 T DE69519127 T DE 69519127T DE 69519127 T DE69519127 T DE 69519127T DE 69519127 T2 DE69519127 T2 DE 69519127T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- methyl
- furanyl
- tetrahydro
- nitroimino
- 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.)
- Expired - Fee Related
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 38
- -1 tetrahydrofuran compound Chemical class 0.000 title claims description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 239000002917 insecticide Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- 239000000126 substance Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000001816 cooling Methods 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000001914 filtration Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 20
- 230000000749 insecticidal effect Effects 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 238000010898 silica gel chromatography Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
- 241000258937 Hemiptera Species 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 241000721621 Myzus persicae Species 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000358422 Nephotettix cincticeps Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 6
- ULDMVHNUHTUOKM-UHFFFAOYSA-N n-[1-(oxolan-2-ylmethyl)-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1OCCC1 ULDMVHNUHTUOKM-UHFFFAOYSA-N 0.000 description 6
- XLLWFWZRQBQJPL-UHFFFAOYSA-N n-[1-(oxolan-3-ylmethyl)-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCCN1CC1COCC1 XLLWFWZRQBQJPL-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241000252826 Brahmaea certhia Species 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- CZFYGUKMSVUSPJ-UHFFFAOYSA-N n-[1-(oxolan-3-ylmethyl)-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1COCC1 CZFYGUKMSVUSPJ-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- PCPUMGYALMOCHF-UHFFFAOYSA-N oxolan-3-ylmethanol Chemical compound OCC1CCOC1 PCPUMGYALMOCHF-UHFFFAOYSA-N 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
- RXIZGBPABNSQPP-UHFFFAOYSA-N 2-(5,5-dimethyloxolan-3-yl)ethanesulfonic acid Chemical compound CC1(C)CC(CCS(O)(=O)=O)CO1 RXIZGBPABNSQPP-UHFFFAOYSA-N 0.000 description 4
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 239000012973 diazabicyclooctane Substances 0.000 description 4
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- LMYHDIBIUBDSBY-UHFFFAOYSA-N n-[1-(oxolan-3-ylmethyl)-3-propanoyl-1,3-diazinan-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(C(=O)CC)CCCN1CC1COCC1 LMYHDIBIUBDSBY-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 4
- 235000019798 tripotassium phosphate Nutrition 0.000 description 4
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 4
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 4
- 235000019801 trisodium phosphate Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000254032 Acrididae Species 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 241001470017 Laodelphax striatella Species 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241001249129 Scirpophaga incertulas Species 0.000 description 3
- 241000985245 Spodoptera litura Species 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- PJTLDTDIKDZRAN-UHFFFAOYSA-N n-[1-[(5,5-dimethyloxolan-3-yl)methyl]-4,5-dihydroimidazol-2-yl]nitramide Chemical compound C1OC(C)(C)CC1CN1C(=N[N+]([O-])=O)NCC1 PJTLDTDIKDZRAN-UHFFFAOYSA-N 0.000 description 3
- AEWVTNDTWXPXET-UHFFFAOYSA-N n-[1-[(5-methyloxolan-3-yl)methyl]-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound C1OC(C)CC1CN1C(=N[N+]([O-])=O)NCCC1 AEWVTNDTWXPXET-UHFFFAOYSA-N 0.000 description 3
- BNBVZUYOFJWGNJ-UHFFFAOYSA-N oxolan-3-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1COCC1 BNBVZUYOFJWGNJ-UHFFFAOYSA-N 0.000 description 3
- 229910000105 potassium hydride Inorganic materials 0.000 description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 3
- 229910001948 sodium oxide Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- AXQYVOIYCYAVSW-UHFFFAOYSA-N 3-(bromomethyl)oxolane Chemical compound BrCC1CCOC1 AXQYVOIYCYAVSW-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
- 241000776777 Cacopsylla mali Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 241000257303 Hymenoptera Species 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
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- 239000005909 Kieselgur Substances 0.000 description 2
- 241001177117 Lasioderma serricorne Species 0.000 description 2
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- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001232130 Maruca testulalis Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000409991 Mythimna separata Species 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
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- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241001439019 Phthorimaea operculella Species 0.000 description 2
- 241000437063 Phyllotreta striolata Species 0.000 description 2
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- 239000008399 tap water Substances 0.000 description 1
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- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
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- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12217994 | 1994-06-03 | ||
| JP06412095A JP4136000B2 (ja) | 1994-06-03 | 1995-03-23 | 殺虫性テトラヒドロフラン系化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69519127D1 DE69519127D1 (de) | 2000-11-23 |
| DE69519127T2 true DE69519127T2 (de) | 2001-05-17 |
Family
ID=26405256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69519127T Expired - Fee Related DE69519127T2 (de) | 1994-06-03 | 1995-06-02 | Inzektizide Tetrahydrofuranverbindung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5614527A (OSRAM) |
| EP (1) | EP0685477B1 (OSRAM) |
| JP (1) | JP4136000B2 (OSRAM) |
| KR (1) | KR0172650B1 (OSRAM) |
| CN (1) | CN1054854C (OSRAM) |
| AU (1) | AU672554B2 (OSRAM) |
| DE (1) | DE69519127T2 (OSRAM) |
| MY (1) | MY114174A (OSRAM) |
| TW (1) | TW307667B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202010006937U1 (de) | 2010-05-18 | 2010-08-12 | Graf von Wengersky, Konstantin, Dr. | Hufnagel |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998014434A1 (en) * | 1996-10-04 | 1998-04-09 | Ube Industries, Ltd. | 4-substituted 5-chloro-6-alkylpyrimidine compounds, process for the preparation of them, and pesticide or acaricide compositions containing the same |
| FR2774644B1 (fr) | 1998-02-12 | 2003-12-05 | Gec Alsthom Transport Sa | Banquette deux places modulable premiere-seconde classe et procede de transformation d'une telle banquette |
| DE19823396A1 (de) | 1998-05-26 | 1999-12-02 | Bayer Ag | Synergistische insektizide Mischungen |
| DE19913174A1 (de) | 1999-03-24 | 2000-09-28 | Bayer Ag | Synergistische insektizide Mischungen |
| DE19948129A1 (de) | 1999-10-07 | 2001-04-12 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10024934A1 (de) * | 2000-05-19 | 2001-11-22 | Bayer Ag | Wirkstoffkombinationen mit insektiziden akariziden Eigenschaften |
| DE102004006075A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| CN1295228C (zh) * | 2004-11-23 | 2007-01-17 | 华东理工大学 | 硝基亚甲基衍生物及其用途 |
| CN101492444B (zh) | 2008-01-23 | 2012-07-04 | 华东理工大学 | 具有杀虫活性的含氮杂环化合物、其制备及用途 |
| CN101503406B (zh) * | 2008-12-17 | 2011-03-23 | 武汉工程大学 | 1-(2,3-环氧丙基)-n-硝基亚咪唑烷-2-基胺及其制备方法和应用 |
| CN101747320B (zh) | 2008-12-19 | 2013-10-16 | 华东理工大学 | 二醛构建的具有杀虫活性的含氮或氧杂环化合物及其制备方法 |
| CN102093389B (zh) | 2009-12-09 | 2014-11-19 | 华东理工大学 | 双联和氧桥杂环新烟碱化合物及其制备方法 |
| EP2635126A1 (en) * | 2010-11-01 | 2013-09-11 | The Agricultural Research Organization | Novel solid bait compositions used for protecting fruits from fruit fly pests |
| CN103271073B (zh) * | 2013-06-18 | 2014-07-30 | 陕西农心作物科技有限公司 | 一种含环氧虫啉和噻嗪酮的杀虫组合物 |
| CN103283770B (zh) * | 2013-06-25 | 2014-12-10 | 陕西农心作物科技有限公司 | 一种含环氧虫啉和氰氟虫腙的杀虫组合物 |
| CN103651507B (zh) * | 2013-11-29 | 2015-08-26 | 许亚萍 | 一种含环氧虫啉与印楝素的杀虫组合物 |
| CN103755667B (zh) * | 2014-01-27 | 2016-01-20 | 苏州大学 | 一种手性3-（2-硝基乙基）四氢呋喃化合物及其制备方法 |
| CN105367557B (zh) * | 2015-11-23 | 2018-04-24 | 安徽千和新材料科技发展有限公司 | 一种环氧啉的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60183271A (ja) * | 1984-02-29 | 1985-09-18 | Ohbayashigumi Ltd | 移動ロボツト |
| JPS6181382A (ja) * | 1984-09-25 | 1986-04-24 | 三菱電機株式会社 | エレベ−タの戸の制御装置 |
| JPH07613B2 (ja) * | 1985-02-12 | 1995-01-11 | 日本バイエルアグロケム株式会社 | ニトロメチレン誘導体、その製法及び殺虫剤 |
| JPS61267575A (ja) * | 1985-05-21 | 1986-11-27 | Nippon Tokushu Noyaku Seizo Kk | ニトロイミノ誘導体、その製法及び殺虫剤 |
| EP0192060B1 (de) * | 1985-02-04 | 1991-09-18 | Nihon Bayer Agrochem K.K. | Heterocyclische Verbindungen |
| JPH0730070B2 (ja) * | 1985-10-03 | 1995-04-05 | 日本バイエルアグロケム株式会社 | 新規複素環式化合物 |
| JPH0784461B2 (ja) * | 1986-12-19 | 1995-09-13 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロイミノ又はシアノイミノ化合物 |
| JP3032846B2 (ja) * | 1990-04-13 | 2000-04-17 | 武田薬品工業株式会社 | グアニジン誘導体の製造方法、その中間体及びその製造方法 |
| JP2973497B2 (ja) * | 1990-09-11 | 1999-11-08 | 日本曹達株式会社 | Ｎ―ニトロイソチオ尿素誘導体の製造法 |
| US8772476B2 (en) * | 2011-10-28 | 2014-07-08 | Honeywell International Inc. | Gas and liquid phase catalytic Beckmann rearrangement of oximes to produce lactams |
-
1995
- 1995-03-23 JP JP06412095A patent/JP4136000B2/ja not_active Expired - Fee Related
- 1995-05-23 US US08/447,962 patent/US5614527A/en not_active Expired - Fee Related
- 1995-05-23 AU AU20197/95A patent/AU672554B2/en not_active Ceased
- 1995-05-25 TW TW084105264A patent/TW307667B/zh active
- 1995-05-26 MY MYPI95001392A patent/MY114174A/en unknown
- 1995-06-02 DE DE69519127T patent/DE69519127T2/de not_active Expired - Fee Related
- 1995-06-02 EP EP95108529A patent/EP0685477B1/en not_active Expired - Lifetime
- 1995-06-02 CN CN95106141A patent/CN1054854C/zh not_active Expired - Fee Related
- 1995-06-03 KR KR1019950014674A patent/KR0172650B1/ko not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202010006937U1 (de) | 2010-05-18 | 2010-08-12 | Graf von Wengersky, Konstantin, Dr. | Hufnagel |
Also Published As
| Publication number | Publication date |
|---|---|
| TW307667B (OSRAM) | 1997-06-11 |
| MY114174A (en) | 2002-08-30 |
| CN1054854C (zh) | 2000-07-26 |
| US5614527A (en) | 1997-03-25 |
| DE69519127D1 (de) | 2000-11-23 |
| AU672554B2 (en) | 1996-10-03 |
| JP4136000B2 (ja) | 2008-08-20 |
| EP0685477B1 (en) | 2000-10-18 |
| KR0172650B1 (ko) | 1999-02-01 |
| CN1119646A (zh) | 1996-04-03 |
| AU2019795A (en) | 1996-01-04 |
| JPH0848682A (ja) | 1996-02-20 |
| EP0685477A1 (en) | 1995-12-06 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |