KR100767229B1 - 치환 아미노퀴나졸리논 (티온) 유도체 또는 그의 염, 그의중간체, 및 해충 억제제 및 그의 사용방법 - Google Patents
치환 아미노퀴나졸리논 (티온) 유도체 또는 그의 염, 그의중간체, 및 해충 억제제 및 그의 사용방법 Download PDFInfo
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- KR100767229B1 KR100767229B1 KR1020000064784A KR20000064784A KR100767229B1 KR 100767229 B1 KR100767229 B1 KR 100767229B1 KR 1020000064784 A KR1020000064784 A KR 1020000064784A KR 20000064784 A KR20000064784 A KR 20000064784A KR 100767229 B1 KR100767229 B1 KR 100767229B1
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- NXBWFXMEJVOABP-UHFFFAOYSA-N 4-amino-1h-quinazolin-2-one Chemical class C1=CC=C2C(N)=NC(=O)NC2=C1 NXBWFXMEJVOABP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 241001061127 Thione Species 0.000 title claims abstract description 33
- 150000003839 salts Chemical class 0.000 title claims abstract description 27
- 241000607479 Yersinia pestis Species 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 13
- 239000000543 intermediate Substances 0.000 title description 5
- -1 (Substituted) amino Chemical group 0.000 claims abstract description 53
- 239000003112 inhibitor Substances 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- FVACZQHQBKPPMX-UHFFFAOYSA-N quinazolin-2-one Chemical compound C1=C[CH]C2=NC(=O)N=CC2=C1 FVACZQHQBKPPMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 106
- 150000001875 compounds Chemical class 0.000 abstract description 94
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 68
- 125000000217 alkyl group Chemical group 0.000 abstract description 36
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 16
- 230000000361 pesticidal effect Effects 0.000 abstract description 11
- 230000000749 insecticidal effect Effects 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 8
- 241000018137 Trialeurodes vaporariorum Species 0.000 abstract description 7
- 239000000575 pesticide Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 7
- 229910052740 iodine Inorganic materials 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 125000005842 heteroatom Chemical group 0.000 abstract description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005544 phthalimido group Chemical group 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000005431 greenhouse gas Substances 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 74
- 125000001424 substituent group Chemical group 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 49
- 125000004414 alkyl thio group Chemical group 0.000 description 46
- 239000012442 inert solvent Substances 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- 125000004093 cyano group Chemical group *C#N 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 125000000304 alkynyl group Chemical group 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 8
- 0 CCC(N(*)C1=CCC(CC(C)(C)*)CC1CN**C)=* Chemical compound CCC(N(*)C1=CCC(CC(C)(C)*)CC1CN**C)=* 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 244000045947 parasite Species 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- 238000003898 horticulture Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000005554 pyridyloxy group Chemical group 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229960004029 silicic acid Drugs 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000254032 Acrididae Species 0.000 description 3
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 3
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 3
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 241001556089 Nilaparvata lugens Species 0.000 description 3
- 241001076439 Oxya hyla intricata Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 231100000225 lethality Toxicity 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 2
- VFSVVFKYFOAIPV-UHFFFAOYSA-N 3-(pyridin-3-ylmethylideneamino)-6-(trifluoromethoxy)-1,4-dihydroquinazolin-2-one Chemical compound C1C2=CC(OC(F)(F)F)=CC=C2NC(=O)N1N=CC1=CC=CN=C1 VFSVVFKYFOAIPV-UHFFFAOYSA-N 0.000 description 2
- TUNLWFFLKJFEMU-UHFFFAOYSA-N 3-amino-6-(1,1,2,2,2-pentafluoroethyl)-1,4-dihydroquinazolin-2-one Chemical compound FC(F)(F)C(F)(F)C1=CC=C2NC(=O)N(N)CC2=C1 TUNLWFFLKJFEMU-UHFFFAOYSA-N 0.000 description 2
- MZWJUZMAXKTGBA-UHFFFAOYSA-N 3-amino-6-(trifluoromethoxy)-1,4-dihydroquinazolin-2-one Chemical compound FC(F)(F)OC1=CC=C2NC(=O)N(N)CC2=C1 MZWJUZMAXKTGBA-UHFFFAOYSA-N 0.000 description 2
- AJBARNADQLELRO-UHFFFAOYSA-N 3-amino-6-hydroxy-1,4-dihydroquinazolin-2-one Chemical compound OC1=CC=C2NC(=O)N(N)CC2=C1 AJBARNADQLELRO-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- AVXPQUZMIHHBFP-UHFFFAOYSA-N 4-amino-1h-quinazoline-2-thione Chemical class C1=CC=C2C(N)=NC(=S)NC2=C1 AVXPQUZMIHHBFP-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000680417 Aphelenchoides ritzemabosi Species 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- 241000254127 Bemisia tabaci Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000630083 Ceroplastes ceriferus Species 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 241001205778 Dialeurodes citri Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241001267621 Tylenchulus semipenetrans Species 0.000 description 2
- 241001630065 Unaspis yanonensis Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000021329 brown rice Nutrition 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- MQHNKCZKNAJROC-UHFFFAOYSA-N phthalic acid dipropyl ester Natural products CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- OUYVLIONOBXWKP-UHFFFAOYSA-N tert-butyl n-(6-hydroxy-2-oxo-1,4-dihydroquinazolin-3-yl)carbamate Chemical compound OC1=CC=C2NC(=O)N(NC(=O)OC(C)(C)C)CC2=C1 OUYVLIONOBXWKP-UHFFFAOYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31229799 | 1999-11-02 | ||
| JP99-312297 | 1999-11-02 | ||
| JP2000-94493 | 2000-03-30 | ||
| JP2000094493 | 2000-03-30 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020070077597A Division KR20070089108A (ko) | 1999-11-02 | 2007-07-25 | 치환 아미노퀴나졸리논 (티온) 유도체 또는 그의 염, 그의중간체, 및 해충 억제제 및 그의 사용방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20010051394A KR20010051394A (ko) | 2001-06-25 |
| KR100767229B1 true KR100767229B1 (ko) | 2007-10-16 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020000064784A Expired - Lifetime KR100767229B1 (ko) | 1999-11-02 | 2000-11-02 | 치환 아미노퀴나졸리논 (티온) 유도체 또는 그의 염, 그의중간체, 및 해충 억제제 및 그의 사용방법 |
| KR1020070077597A Withdrawn KR20070089108A (ko) | 1999-11-02 | 2007-07-25 | 치환 아미노퀴나졸리논 (티온) 유도체 또는 그의 염, 그의중간체, 및 해충 억제제 및 그의 사용방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020070077597A Withdrawn KR20070089108A (ko) | 1999-11-02 | 2007-07-25 | 치환 아미노퀴나졸리논 (티온) 유도체 또는 그의 염, 그의중간체, 및 해충 억제제 및 그의 사용방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6455535B1 (enExample) |
| EP (1) | EP1097932B1 (enExample) |
| KR (2) | KR100767229B1 (enExample) |
| CN (3) | CN1666983B (enExample) |
| AR (1) | AR032605A1 (enExample) |
| BR (1) | BR0005220B1 (enExample) |
| CO (1) | CO5221059A1 (enExample) |
| CZ (1) | CZ301575B6 (enExample) |
| DE (1) | DE60043806D1 (enExample) |
| EG (1) | EG22880A (enExample) |
| ES (1) | ES2338629T3 (enExample) |
| HU (1) | HU229882B1 (enExample) |
| ID (1) | ID27911A (enExample) |
| IL (1) | IL139199A (enExample) |
| MY (1) | MY126059A (enExample) |
| TW (1) | TWI252850B (enExample) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1626047T3 (pl) * | 2003-05-12 | 2011-05-31 | Nihon Nohyaku Co Ltd | Sposób wytwarzania podstawionej pochodnej aminochinazolinonu jako środka do zwalczania insektów |
| ATE406348T1 (de) | 2004-09-23 | 2008-09-15 | Schering Plough Ltd | Bekämpfung von parasiten in tieren durch verwendung neuer trifluormethansulfonanilidoximetherderivate |
| US7820649B2 (en) | 2006-09-11 | 2010-10-26 | N.V. Organon | Quinazolinone and isoquinolinone acetamide derivatives |
| ATE549325T1 (de) | 2007-01-26 | 2012-03-15 | Basf Se | 3-amino-1,2-benzisothiazol-verbindungen zur bekämpfung von tierpest ii |
| EP2679095A1 (en) | 2007-02-06 | 2014-01-01 | Basf Se | Pesticidal mixtures |
| MX2009011456A (es) | 2007-04-23 | 2009-11-05 | Basf Se | Aumento de la productividad de las plantas por combinacion de agentes quimicos con modificaciones transgenicas. |
| EP2008521A1 (en) * | 2007-06-28 | 2008-12-31 | Syngeta Participations AG | Methods of controlling insects |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| JP2011510033A (ja) | 2008-01-25 | 2011-03-31 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 化合物 |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2227951A1 (de) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren |
| CN102300456B (zh) | 2009-01-27 | 2014-11-12 | 巴斯夫欧洲公司 | 拌种方法 |
| WO2010089244A1 (en) | 2009-02-03 | 2010-08-12 | Basf Se | Method for dressing seeds |
| AU2010220293B2 (en) | 2009-03-04 | 2014-09-11 | Basf Se | 3-arylquinazolin-4-one compounds for combating invertebrate pests |
| US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
| BR112012002164B1 (pt) | 2009-07-30 | 2021-04-20 | Merial, Inc | compostos inseticidas de 4-amino-tieno[2,3-d]-pirimidina e métodos para seu uso |
| WO2011117286A1 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| EP2563128A1 (en) * | 2010-04-27 | 2013-03-06 | Syngenta Participations AG | Methods of controlling neonicotinoid resistant aphids |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| EP2564697A1 (en) | 2011-08-29 | 2013-03-06 | Syngenta Participations AG. | Methods of controlling insects |
| CN103130771B (zh) * | 2011-11-25 | 2015-02-11 | 中国中化股份有限公司 | 6-取代苯基喹唑啉酮类化合物及其用途 |
| CN102415394A (zh) * | 2011-12-06 | 2012-04-18 | 海利尔药业集团股份有限公司 | 含有茚虫威的高效杀虫组合物 |
| CN104650038B (zh) * | 2013-11-25 | 2018-06-08 | 沈阳中化农药化工研发有限公司 | 6-取代吡啶基喹唑啉酮类化合物及其用途 |
| CN104650036B (zh) * | 2013-11-25 | 2017-07-21 | 沈阳中化农药化工研发有限公司 | 6‑取代苯基喹唑啉酮类化合物及其用途 |
| CN103728407B (zh) * | 2014-01-20 | 2015-08-26 | 崔淑华 | 一种Pyrifluquinazon残留量的测定方法 |
| AR100304A1 (es) | 2014-02-05 | 2016-09-28 | Basf Corp | Formulación de recubrimiento de semillas |
| CN104904719B (zh) * | 2014-03-11 | 2018-09-28 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制有害生物的方法 |
| CN105076142B (zh) * | 2014-05-08 | 2017-09-01 | 江苏龙灯化学有限公司 | 一种作物保护剂 |
| CN105418590B (zh) * | 2014-09-18 | 2018-06-29 | 沈阳中化农药化工研发有限公司 | 6-取代吡唑基喹唑啉酮类化合物及其用途 |
| CN105707078B (zh) * | 2014-12-04 | 2018-09-28 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105707115B (zh) * | 2014-12-04 | 2018-09-28 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105638687B (zh) * | 2014-12-04 | 2018-02-13 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105707111B (zh) * | 2014-12-04 | 2018-09-28 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105732587B (zh) * | 2014-12-12 | 2018-08-24 | 沈阳中化农药化工研发有限公司 | 6-取代嘧啶基喹唑啉酮类化合物及其用途 |
| CN105794814B (zh) * | 2014-12-30 | 2019-01-08 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105794812B (zh) * | 2014-12-30 | 2019-01-29 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105794810B (zh) * | 2014-12-30 | 2019-01-29 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN105794811B (zh) * | 2014-12-30 | 2019-01-29 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业害虫的方法 |
| CN104824009B (zh) * | 2015-04-28 | 2018-08-14 | 广东中迅农科股份有限公司 | 含有吡啶喹唑啉和氟啶虫胺腈的杀虫组合物 |
| CN107751205A (zh) * | 2016-08-16 | 2018-03-06 | 江苏龙灯化学有限公司 | 一种杀虫组合物及其控制农业有害生物的方法 |
| WO2019224143A1 (de) | 2018-05-24 | 2019-11-28 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
| CN109705094A (zh) * | 2019-02-15 | 2019-05-03 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉的制备方法 |
| CN110698416B (zh) * | 2019-12-16 | 2020-03-20 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉中间体的制备方法 |
| CN111533701B (zh) * | 2020-07-02 | 2020-10-16 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉中间体的合成方法 |
| CN111887255A (zh) * | 2020-07-13 | 2020-11-06 | 山东康乔生物科技有限公司 | 一种含有螺甲螨酯和吡啶喹唑啉的农药组合物及其应用 |
| CN111704604B (zh) * | 2020-08-19 | 2020-11-17 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉的制备方法 |
| CN111808075B (zh) * | 2020-09-07 | 2020-12-08 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉中间体的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0735035A1 (en) * | 1995-03-31 | 1996-10-02 | Nihon Nohyaku Co., Ltd. | Substituted aminoquinazolinone (thione) derivatives or salts thereof, intermediates thereof, and pest controllers and a method for using the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0840477B1 (en) * | 1996-10-31 | 2012-07-18 | Panasonic Corporation | Secret key transfer method which is highly secure and can restrict the damage caused when the secret key is leaked or decoded |
-
2000
- 2000-10-23 IL IL139199A patent/IL139199A/en active IP Right Grant
- 2000-10-24 MY MYPI20004998A patent/MY126059A/en unknown
- 2000-10-25 CZ CZ20003953A patent/CZ301575B6/cs not_active IP Right Cessation
- 2000-10-27 AR ARP000105675A patent/AR032605A1/es not_active Application Discontinuation
- 2000-10-31 TW TW089122882A patent/TWI252850B/zh not_active IP Right Cessation
- 2000-10-31 HU HU0004212A patent/HU229882B1/hu not_active IP Right Cessation
- 2000-11-01 EG EG20001381A patent/EG22880A/xx active
- 2000-11-01 US US09/702,757 patent/US6455535B1/en not_active Expired - Lifetime
- 2000-11-01 ID IDP20000940A patent/ID27911A/id unknown
- 2000-11-01 CO CO00083069A patent/CO5221059A1/es not_active Application Discontinuation
- 2000-11-01 BR BRPI0005220-5A patent/BR0005220B1/pt not_active IP Right Cessation
- 2000-11-02 ES ES00123887T patent/ES2338629T3/es not_active Expired - Lifetime
- 2000-11-02 KR KR1020000064784A patent/KR100767229B1/ko not_active Expired - Lifetime
- 2000-11-02 CN CN2005100601733A patent/CN1666983B/zh not_active Expired - Fee Related
- 2000-11-02 CN CN001368583A patent/CN1302801B/zh not_active Expired - Fee Related
- 2000-11-02 DE DE60043806T patent/DE60043806D1/de not_active Expired - Lifetime
- 2000-11-02 CN CN201310073833.6A patent/CN103288754B/zh not_active Expired - Lifetime
- 2000-11-02 EP EP00123887A patent/EP1097932B1/en not_active Expired - Lifetime
-
2007
- 2007-07-25 KR KR1020070077597A patent/KR20070089108A/ko not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0735035A1 (en) * | 1995-03-31 | 1996-10-02 | Nihon Nohyaku Co., Ltd. | Substituted aminoquinazolinone (thione) derivatives or salts thereof, intermediates thereof, and pest controllers and a method for using the same |
Non-Patent Citations (1)
| Title |
|---|
| Pesticide Science vol. 55, no. 3, p 359-362(1999. 3 발행) * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1666983A (zh) | 2005-09-14 |
| US6455535B1 (en) | 2002-09-24 |
| HUP0004212A3 (en) | 2002-02-28 |
| EP1097932A1 (en) | 2001-05-09 |
| CN103288754B (zh) | 2016-03-02 |
| HU0004212D0 (enExample) | 2001-01-29 |
| CO5221059A1 (es) | 2002-11-28 |
| CZ20003953A3 (en) | 2001-06-13 |
| IL139199A0 (en) | 2001-11-25 |
| HUP0004212A2 (hu) | 2001-11-28 |
| BR0005220A (pt) | 2001-06-19 |
| DE60043806D1 (de) | 2010-03-25 |
| CN103288754A (zh) | 2013-09-11 |
| CN1302801B (zh) | 2013-03-20 |
| KR20070089108A (ko) | 2007-08-30 |
| MY126059A (en) | 2006-09-29 |
| TWI252850B (en) | 2006-04-11 |
| IL139199A (en) | 2006-10-31 |
| EP1097932B1 (en) | 2010-02-10 |
| CN1666983B (zh) | 2010-05-05 |
| ES2338629T3 (es) | 2010-05-11 |
| CN1302801A (zh) | 2001-07-11 |
| AR032605A1 (es) | 2003-11-19 |
| CZ301575B6 (cs) | 2010-04-21 |
| EG22880A (en) | 2003-10-30 |
| KR20010051394A (ko) | 2001-06-25 |
| BR0005220B1 (pt) | 2010-11-03 |
| ID27911A (id) | 2001-05-03 |
| HU229882B1 (hu) | 2014-11-28 |
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