CN1302801A - 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 - Google Patents
取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 Download PDFInfo
- Publication number
- CN1302801A CN1302801A CN00136858A CN00136858A CN1302801A CN 1302801 A CN1302801 A CN 1302801A CN 00136858 A CN00136858 A CN 00136858A CN 00136858 A CN00136858 A CN 00136858A CN 1302801 A CN1302801 A CN 1302801A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- halo
- group
- alkylthio
- alkoxyl
- 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
- 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 34
- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- 125000005323 thioketone group Chemical class 0.000 title claims description 39
- 241000607479 Yersinia pestis Species 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 248
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 190
- -1 (substituted) aminocarbonyl group Chemical group 0.000 claims abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 147
- 125000004414 alkyl thio group Chemical group 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000001246 bromo group Chemical group Br* 0.000 claims description 53
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 50
- 125000000304 alkynyl group Chemical group 0.000 claims description 49
- 241000238631 Hexapoda Species 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 230000001473 noxious effect Effects 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- VSQUZVLNMULDCY-UHFFFAOYSA-N [O].C1=CC=NC=C1 Chemical class [O].C1=CC=NC=C1 VSQUZVLNMULDCY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 125000000815 N-oxide group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- 241001061127 Thione Species 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 description 90
- 238000006243 chemical reaction Methods 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 238000002360 preparation method Methods 0.000 description 34
- 230000000704 physical effect Effects 0.000 description 32
- 239000012442 inert solvent Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 230000001276 controlling effect Effects 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000000749 insecticidal effect Effects 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
- 230000035484 reaction time Effects 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000003513 alkali Substances 0.000 description 11
- 241001556089 Nilaparvata lugens Species 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 description 8
- 235000010755 mineral Nutrition 0.000 description 8
- 239000011707 mineral Substances 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 7
- 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
- 241000244206 Nematoda Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 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 5
- 241000272639 Brachycaudus mimeuri Species 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 241000819999 Nymphes Species 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 244000045947 parasite Species 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 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
- 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
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical group C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
- JIKWROZITANUAR-UHFFFAOYSA-N 3-(pyridin-3-ylmethylamino)-6-(trifluoromethoxy)-1,4-dihydroquinazolin-2-one Chemical compound C1C2=CC(OC(F)(F)F)=CC=C2NC(=O)N1NCC1=CC=CN=C1 JIKWROZITANUAR-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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 241001220428 Aphelenchus avenae Species 0.000 description 2
- 241000254127 Bemisia tabaci Species 0.000 description 2
- 241000982105 Brevicoryne brassicae Species 0.000 description 2
- 241000675108 Citrus tangerina Species 0.000 description 2
- 241000586568 Diaspidiotus perniciosus Species 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241001442497 Globodera rostochiensis Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241000270322 Lepidosauria Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GQLSEYOOXBRDFZ-UHFFFAOYSA-N N-formylnornicotine Natural products O=CN1CCCC1C1=CC=CN=C1 GQLSEYOOXBRDFZ-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 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
- 239000013543 active substance Substances 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000005183 environmental health Effects 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005180 public health Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XLYPHUGUKGMURE-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzaldehyde Chemical class OC1=CC=C([N+]([O-])=O)C(C=O)=C1 XLYPHUGUKGMURE-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241000294569 Aphelenchoides Species 0.000 description 1
- 241000680417 Aphelenchoides ritzemabosi Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- STJDFMVGMSIODT-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1C(N(C2=CC=C(C=C2C1)O)N)=O Chemical compound C(C)(C)(C)OC(=O)N1C(N(C2=CC=C(C=C2C1)O)N)=O STJDFMVGMSIODT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001450758 Ceroplastes Species 0.000 description 1
- 241000630083 Ceroplastes ceriferus Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001205778 Dialeurodes citri Species 0.000 description 1
- 241000526125 Diaphorina citri Species 0.000 description 1
- QWDBCIAVABMJPP-UHFFFAOYSA-N Diisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)C QWDBCIAVABMJPP-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241001222563 Empoasca onukii Species 0.000 description 1
- 241000086608 Empoasca vitis Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000193977 Pratylenchus musicola Species 0.000 description 1
- 241001630079 Pseudaonidia duplex Species 0.000 description 1
- 241001446203 Pulvinaria aurantii Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000176086 Sogatella furcifera Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001161749 Stenchaetothrips biformis Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241000661936 Trigonotylus Species 0.000 description 1
- 241000243782 Tylenchida Species 0.000 description 1
- 241001267621 Tylenchulus semipenetrans Species 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- 101100020289 Xenopus laevis koza gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 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
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical class COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012188 paraffin wax 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
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
Abstract
Description
No. | Xn | Y | 物理性质 |
Ⅱ-1Ⅱ-2Ⅱ-3Ⅱ-4Ⅱ-5Ⅱ-6Ⅱ-7Ⅱ-8Ⅱ-9Ⅱ-10Ⅱ-11Ⅱ-12Ⅱ-13Ⅱ-14Ⅱ-15Ⅱ-16Ⅱ-17Ⅱ-18Ⅱ-19Ⅱ-20Ⅱ-21Ⅱ-22Ⅱ-23Ⅱ-24 | 5-OH6-OH7-OH8-OH5-Br6-Br7-Br8-Br5-I6-I7-I8-I5-CF36-CF37-CF38-CF35-C2F56-C2F57-C2F58-C2F55-i-C3F76-i-C3F77-i-C3F78-i-C3F7 | OOOOOOOOOOOOOOOOOOOOOOOO | 晶体晶体晶体晶体晶体m.p.202.3-205.0℃m.p.155-157.7℃m.p.178.4-183.5℃m.p.147.6-149.5℃ |
No. | Xn | Y | 物理性质 |
Ⅱ-25Ⅱ-26Ⅱ-27Ⅱ-28Ⅱ-29Ⅱ-30Ⅱ-31Ⅱ-32Ⅱ-33Ⅱ-34Ⅱ-35Ⅱ-36Ⅱ-37Ⅱ-38Ⅱ-39Ⅱ-40Ⅱ-41Ⅱ-42Ⅱ-43Ⅱ-44Ⅱ-45Ⅱ-46Ⅱ-47Ⅱ-48 | 5-n-C6F136-n-C6F137-n-C6F138-n-C6F135-OCF36-OCF37-OCF38-OCF35-OCH2-Ph6-OCH2-Ph7-OCH2-Ph8-OCH2-Ph5-OCHF26-OCHF27-OCHF28-OCHF25-SCF36-SCF37-SCF38-SCF35-SC2F56-SC2F57-SC2F58-SC2F5 | OOOOOOOOOOOOOOOOOOOOOOOO | 晶体m.p.181.5-184.0℃晶体晶体晶体 |
No. | Xn | Y | 物理性质 |
Ⅱ-49Ⅱ-50Ⅱ-51Ⅱ-52Ⅱ-53Ⅱ-54Ⅱ-55Ⅱ-56Ⅱ-57Ⅱ-58Ⅱ-59Ⅱ-60Ⅱ-61Ⅱ-62Ⅱ-63Ⅱ-64Ⅱ-65Ⅱ-66Ⅱ-67Ⅱ-68Ⅱ-69Ⅱ-70Ⅱ-71Ⅱ-72 | 5-S-i-C3F76-S-i-C3F77-S-i-C3F78-S-i-C3F75-SOCF36-SOCF37-SOCF38-SOCF35-SO2CF36-SO2CF37-SO2CF38-SO2CF35-SOC2F56-SOC2F57-SOC2F58-SOC2F55-SO2C2F56-SO2C2F57-SO2C2F58-SO2C2F55-SO-i-C3F76-SO-i-C3F77-SO-i-C3F78-SO-i-C3F7 | OOOOOOOOOOOOOOOOOOOOOOOO | m.p.71.2-73.5℃ |
No. | Xn | Y | 物理性质 |
Ⅱ-73Ⅱ-74Ⅱ-75Ⅱ-76Ⅱ-77Ⅱ-78Ⅱ-79Ⅱ-80Ⅱ-81Ⅱ-82Ⅱ-83Ⅱ-84Ⅱ-85Ⅱ-86Ⅱ-87Ⅱ-88Ⅱ-89Ⅱ-90Ⅱ-91Ⅱ-92Ⅱ-93Ⅱ-94Ⅱ-95Ⅱ-96 | 5-SO2-i-C3F76-SO2-i-C3F77-SO2-i-C3F78-SO2-i-C3F75-COOC2H56-COOC2H57-COOC2H58-COOC2H55-COOH6-COOH7-COOH8-COOH5-Ph6-Ph7-Ph8-Ph5-(p-Cl-Ph)6-(p-Cl-Ph)7-(p-Cl-Ph)8-(p-Cl-Ph)5-O-Ph6-O-Ph7-O-Ph8-O-Ph | OOOOOOOOOOOOOOOOOOOOOOOO |
No. | Xn | Y | 物理性质 |
Ⅱ-97Ⅱ-98Ⅱ-99Ⅱ-100Ⅱ-101Ⅱ-102Ⅱ-103Ⅱ-104Ⅱ-105Ⅱ-106Ⅱ-107Ⅱ-108 | 5-n-C4H96-n-C4H97-n-C4H98-n-C4H95-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF26-OCF2CHFOCF36-OCH(CF3)26-O-(m-CF3-Ph)6-O-(3-Cl-5-CF3-2-Pyr) | OOOOOOOOOOOO | m.p.194.8℃晶体m.p.238.8-241.0℃m.p.204.7-207.9℃晶体 |
No. | 1H-NMR[DMSO-d6/TMS,δ(ppm)] |
Ⅱ-1Ⅱ-2Ⅱ-3Ⅱ-4Ⅱ-6Ⅱ-18Ⅱ-26Ⅱ-33Ⅱ-36Ⅱ-38Ⅱ-105Ⅱ-108 | 4.36(2H,s),4.65(2H,br),6.20(1H,d),6.34(1H,d),6.89(1H,t),9.12(1H,br),9.62(1H,s).4.4 5(2H,s),4.65(2H,s),6.51-6.63(3H,m),9.00(1H,s),9.60(1H,brs).4.48(2H,s),4.65(2H,s),6.23-6.35(2H,m),6.85(1H,d),9.05(1H,s),9.63(1H,s)4.4 6(2H,s),4.65(2H,s),6.57(1H,d),6.64-6.74(2H,m),7.95(1H,d),9.60(1H,brs).4.48(2H,s),4.66(2H,s),6.74(1H,m),7.18(1H,m),7.30(1H,m),9.43(1H,s).4.56(2H,s),4.70(2H,s),6.95(1H,d),7.40-7.50(2H,m),9.83(1H,s).4.56(2H,s),4.70(2H,s),6.94(1H,d),7.43-7.48(2H,m),9.74(1H,s).4.48(2H,s),4.69(2H,s),5.00(2H,s),6.30(1H,d),6.45(1H,d),7.05(1H,t),7.25-7.40(6H,m).4.48(2H,s),4.68(2H,s),5.19(2H,s),6.71(1H,d),6.82(1H,t),6.92(1H,d),7.30-7.40(3H,m),7.51(2H,d),8.18(1H,s).4.48(2H,s),4.65(2H,s),6.76-6.79(1H,d,J=8.7Hz),6.95-7.00(2H,m),6.80-7.30(1H,t,J=7.46),9.37(1H,s).4.88(2H,s),4.64(2H,s),6.79(1H,d,J=11.6Hz),7.00(1H,s),7.06(1H,m),7.23(1H,t,J=4Hz),9.43(1H,s).4.46(2H,s),4.65(2H,s),6.80(1H,d,J=11.2Hz),7.01(2H,m),8.48(1H,s),8.52(1H,s),9.38(1H,s). |
No. | R | Xn | 物理性质 |
123456789101112131415161718192021222324 | HHHHHHHHHHHHHHHHHHHHHHHH | 5-OH6-OH7-OH8-OH5-Br6-Br7-Br8-Br5-I6-I7-I8-I5-CF36-CF37-CF38-CF35-C2F56-C2F57-C2F58-C2F55-i-C3F76-i-C3F77-i-C3F78-i-C3F7 | m.p.293-295℃m.p.>300℃m.p.>300℃m.p.>300℃m.p.227.6-286.7℃m.p.298-300℃m.p.>300℃ |
No. | R | Xn | 物理性质 |
252627282930313233343536373839404142434445464748 | HHHHHHHHHHHHHHHHHHHHHHHH | 5-n-C6F136-n-C6F137-n-C6F138-n-C6F135-OCF36-OCF37-OCF38-OCF35-CH2-Ph6-CH2-Ph7-CH2-Ph8-CH2-Ph5-OCHF26-OCHF27-OCHF28-OCHF25-SCF36-SCF37-SCF38-SCF35-SC2F56-SC2F57-SC2F58-SC2F5 | m.p.>300℃m.p.264.0-266.0℃m.p.260.1-264.5℃ |
No. | R | Xn | 物理性质 |
495051525354555657585960616263646566676869707172 | HHHHHHHHHHHHHHHHHHHHHHHH | 5-S-i-C3F76-S-i-C3F77-S-i-C3F78-S-i-C3F75-SOCF36-SOCF37-SOCF38-SOCF35-SO2CF36-SO2CF37-SO2CF38-SO2CF35-SOC2F56-SOC2F57-SOC2F58-SOC2F55-SO2C2F56-SO2C2F57-SO2C2F58-SO2C2F55-SO-i-C3F76-SO-i-C3F77-SO-i-C3F78-SO-i-C3F7 | m.p.252.4-255.0℃ |
No. | R | Xn | 物理性质 |
737475767778798081828384858687888990919293949596 | HHHHHHHHHHHHHHHHHHHHHHHH | 5-SO2-i-C3F76-SO2-i-C3F77-SO2-i-C3F78-SO2-i-C3F75-COOC2H56-COOC2H57-COOC2H58-COOC2H55-COOH6-COOH7-COOH8-COOH5-Ph6-Ph7-Ph8-Ph5-(4-Cl-Ph)6-(4-Cl-Ph)7-(4-Cl-Ph)8-(4-Cl-ph)5-O-Ph6-O-Ph7-O-Ph8-O-Ph | m.p.274-278℃m.p.250.9-253.8℃m.p.276-278℃ |
No. | R | Xn | 物理性质 |
979899100101102103104105106107108109110111112113114115116117118119120 | HHHHCH3CH3CH3CH3C2H5C2H5C2H5C2H5n-C5H11n-C5H11n-C5H11n-C5H11CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2CH=CH2CH2CH=CH2CH2CH=CH2CH2CH=CH2 | 5-n-C4H96-n-C4H97-n-C4H98-n-C4H95-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I | m.p.181.4-185.3℃m.p.191.5-194.5℃nD1.4126(28.5℃)m.p.214-217℃m.p.162-164℃ |
No. | R | Xn | 物理性质 |
12112212312412512612712812913013l132133134135136137138139140141142143144 | CH2OC2H5CH2OC2H5CH2OC2H5CH2OC2H5CH2(4-Cl-Ph)CH2(4-Cl-Ph)CH2(4-Cl-Ph)CH2(4-Cl-Ph)COCH3COCH3COCH3COCH3COC2H5COC2H5COC2H5COC2H5SO2CH3SO2CH3SO2CH3SO2CH3SO2PhSO2PhSO2PhSO2Ph | 5-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I5-I6-I7-I8-I | m.p.111.3-161.7℃m.p.146-149℃m.p.186-188℃m.p.135-139℃m.p.174-181℃m.p.199-205℃ |
No. | R | Xn | 物理性质 |
145146147148149150151152153154155156157158159160161162163164165166167168 | HHHHCO-c-C3H5CO-c-C3H5CO-c-C3H5CO-c-C3H5HHHHHHHHHHHHHHHH | 5-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-I6-I7-I8-I5-(4-CH3O-Ph)6-(4-CH3O-Ph)7-(4-CH3O-Ph)8-(4-CH3O-Ph)5-(3-CH3O-Ph6-(3-CH3O-Ph)7-(3-CH3O-Ph)8-(3-CH3O-Ph)5-(3-NO2-Ph)6-(3-NO2-Ph)7-(3-NO2-Ph)8-(3-NO2-Ph)5-COOH6-COOH7-COOH8-COOH | m.p.251.6-263.3℃m.p.172-175℃m.p.242℃m.p.192-199℃m.p.>300℃m.p.>300℃ |
No | R | R1 | Xn | 物理性质 |
17918018l182183184185186187188189190191192193194195196197198199200201202 | HHHHHHHHHHHHHHHHHHHHHHHH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-OH6-OH7-OH8-OH5-Br6-Br7-Br8-Br5-I6-I7-I8-I5-CF36-CF37-CF38-CF35-C2F56-C2F57-C2F58-C2F55-i-C3F76-i-C3F77-i-C3F78-i-C3F7 | m.p.223-225℃m.p.258-259℃m.p.177-180℃m.p.>300℃m.p.191.0-193.1℃m.p.159.4-161.0℃ |
No | R | R1 | Xn | 物理性质 |
203204205206207208209210211212213214215216217218219220221222223224225226 | HHHHHHHHHHHHHHHHHHHHHHHH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-n-C6F136-n-C6F137-n-C6F138-n-C6F135-OCF36-OCF37-OCF38-OCF35-CH2-Ph6-CH2-Ph7-CH2-Ph8-CH2-Ph5-OCHF26-OCHF27-OCHF28-OCHF25-SCF36-SCF37-SCF38-SCF35-SC2F56-SC2F57-SC2F58-SC2F5 | m.p.153.9-164.7℃nD1.5233(22.6℃)m.p.129.7-130.2℃ |
No | R | R1 | Xn | 物理性质 |
227228229230231232233234235236237238239240241242243244245246247248249250 | HHHHHHHHHHHHHHHHHHHHHHHH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-S-i-C3F76-S-i-C3F77-S-i-C3F78-S-i-C3F75-SOCF36-SOCF37-SOCF38-SOCF35-SO2CF36-SO2CF37-SO2CF38-SO2CF35-SOC2F56-SOC2F57-SOC2F58-SOC2F55-SO2C2F56-SO2C2F57-SO2C2F58-SO2C2F55-SO-i-C3F76-SO-i-C3F77-SO-i-C3F78-SO-i-C3F7 | m.p.50.3-53.1℃ |
No | R | R1 | Xn | 物理性质 |
251252253254255256257258259260261262263264265266267268269270271272273274 | HHHHHHHHHHHHHHHHHHHHHHHH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-SO2-i-C3F76-SO2-i-C3F77-SO2-i-C3F78-SO2-i-C3F75-COOC2H56-COOC2H57-COOC2H58-COOC2H55-COOH6-COOH7-COOH8-COOH5-Ph6-Ph7-Ph8-Ph5-(4-Cl-Ph)6-(4-Cl-Ph)7-(4-Cl-Ph)8-(4-Cl-Ph)5-O-Ph6-O-ph7-O-Ph8-O-Ph |
No | R | R1 | Xn | 物理性质 |
275276277278279280281282283284285286287288289290291292293294295296297 | HHHHHHHHHHHHHCH3CH3CH3CH3C2H5C2H5C2H5C2H5COCH3COCH3 | Q2Q2Q2Q2Q2Q2Q2Q2Q5Q5Q5Q5Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-n-C4H96-n-C4H97-n-C4H98-n-C4H95-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-CF(CF3)26-CF(CF3)27-CF(CF3)28-CF(CF3)26-CF(CF3)25-OCF36-OCF37-OCF38-OCF35-OCF36-OCF37-OCF38-OCF35-OCF36-OCF3 | m.p.168.7-173.9℃m.p.239.7-243.5℃m.p.209.9-213.4℃(R3=COCF3)nD1.5467(23.6℃)nD1.5360(24.3℃)nD1.5478(24.1℃) |
No | R | R1 | Xn | 物理性质 |
298299300301302303304305306307308309310311312313324315316317318319320 | COCH3COCH3COC2H5COC2H5COC2H5COC2H5CH2CH=CH2CH2CH=CH2CH2CH=CH2CH2CH=CH2CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH(CH3)2CH(CH3)2CH(CH3)2CH(CH3)2HCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 7-OCF38-OCF35-OCF36-OCF37-OCF38-OCF35-OCF36-OCF37-OCF38-OCF35-OCF36-OCF37-OCF38-OCF35-OCF36-OCF37-OCF38-OCF36-OCF35-Br6-Br7-Br8-Br | nD1.5174(25.9℃)m.p.92.5℃nD1.5325(24.2℃)nD1.5370(24.8℃)nD1.5380(26.0℃)(R3=COC2H5)nD1.5760(26.2℃) |
No | R | R1 | Xn | 物理性质 |
321322323324325326327328329330331332333334335336337338339340341342343344 | CH2SCH3CH2SCH3CH2SCH3CH2SCH3C2H5C2H5C2H5C2H5i-C3H7i-C3H7i-C3H7i-C3H7COCH3COCH3COCH3COCH3COC2H5COC2H5COC2H5COC2H5CH2-(4-Cl-Ph)CH2-(4-Cl-Ph)CH2-(4-Cl-Ph)CH2-(4-Cl-Ph) | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-Br6-Br7-Br8-Br5-Br6-Br7-Br8-Br5-Br6-Br7-Br8-Br5-Br6-Br7-Br8-Br5-Br6-Br7-Br8-Br5-Br6-Br7-Br8-Br | nD1.6030(27.0℃)nD1.5974(26.9℃)nD1.4680(28.0℃)nD1.5930(27.2℃)nD1.5861(26.8℃)nD1.5885(27.3℃) |
No | R | R1 | Xn | 物理性质 |
345346347348349350351352353354355356357358359360361362363364365366367368 | CO-PhCO-PhCO-PhCO-PhCH3CH3CH3CH3C2H5C2H5C2H5C2H5n-C8H17n-C8H17n-C8H17n-C8H17CH2-(2-NO2-Ph)CH2-(2-NO2-Ph)CH2-(2-NO2-Ph)CH2-(2-NO2-Ph)i-C4H9i-C4H9i-C4H9i-C4H9 | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-Br6-Br7-Br8-Br5-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF5-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF2 | m.p.>300℃nD1.5613(27.9℃)nD1.5354(26.4℃)nD1.5590(25.8℃)nD1.5917(27.9℃)nD1.5557(26.4℃) |
No | R | R1 | Xn | 物理性质 |
369370371372373374375376377378379380381382383384385386387388389390391392 | CH2-(4-CH3O-Ph)CH2-(4-CH3O-Ph)CH2-(4-CH3O-Ph)CH2-(4-CH3O-Ph)COCH3COCH3COCH3COCH3COC2H5COC2H5COC2H5COC2H5CO-i-C3H7CO-i-C3H7CO-i-C3H7CO-i-C3H7CO-Q11CO-Q11CO-Q11CO-Q11CH3CH3CH3CH3 | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF25-OCHF26-OCHF27-OCHF28-OCHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF2 | nD1.5668(26.5℃)nD1.5503(26.1℃)nD1.5470(26.2℃)nD1.5196(28.3℃)m.p.148-155℃nD1.5320(26.2℃) |
No | R | R1 | Xn | 物理性质 |
393394395396397398399400401402403404405406407408409410411412413414415416 | C2H5C2H5C2H5C2H5SO2C2H5SO2C2H5SO2C2H5SO2C2H5CH2OCH2-PhCH2OCH2-PhCH2OCH2-PhCH2OCH2-PhCOOC4H9-tCOOC4H9-tCOOC4H9-tCOOC4H9-tCOCH3COCH3COCH3COCH3COC2H5COC2H5COC2H5COC2H5 | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF2 | nD1.5239(26.7℃)nD1.5309(26.0℃)nD1.5486(26.2℃)nD1.5103(26.2℃)nD1.5262(25.8℃)nD1.5266(25.9℃) |
No | R | R1 | Xn | 物理性质 |
417418419420421422423424425426427428429430431432433434435436437438 | CH2OCH3CH2OCH3CH2OCH3CH2OCH3CH2-Q2CH2-Q2CH2-Q2CH2-Q2SO2CH3SO2CH3SO2CH3SO2CH3SO2C2H5SO2C2H5SO2C2H5SO2C2H5SO2(4-CH3-Ph)SO2(4-CH3-Ph)SO2(4-CH3-Ph)SO2(4-CH3-Ph)HH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-OCF2CHF26-OCF2CHF27-OCF2CHF28-OCF2CHF25-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i6-C3F7-i6-C3F7-i | nD1.5311(23.9℃)nD1.5560(26.8℃)m.p.154-156℃m.p.45-50℃m.p.65-75℃m.p.186-212℃(盐酸盐)m.p.168-208.8℃(硫酸盐) |
No | R | R1 | Xn | 物理性质 |
439440441442443444445446447448449450451452453454455456457458459460461462 | CO-PhCO-PhCO-PhCO-PhCOC3H7-iCOC3H7-iCOC3H7-iCOC3H7-iCOCH3COCH3COCH3COCH3COC2H5COC2H5COC2H5COC2H5COC3H7-nCOC3H7-nCOC3H7-nCOC3H7-nCH3CH3CH3CH3 | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i | m.p.161-165℃nD1.5051(22.1℃)m.p.132-134℃m.p.108℃nD1.510(22.2℃)m.p.67-75℃ |
No | R | R1 | Xn | 物理性质 |
463464465466467468469470471472473474475476477478479480481482483484485486 | C2H5C2H5C2H5C2H5COC2H5COC2H5COC2H5COC2H5HHHHCOC2H5COC2H5COC2H5COC2H5HHHHHCH2C≡CHCH2OCH3CH2SCH3 | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 5-C3F7-i6-C3F7-i7-C3F7-i8-C3F7-i5-F6-F7-F8-F5-COOC2H56-COOC2H57-COOC2H58-COOC2H55-CF36-CF37-CF38-CF35-C2F56-C2F57-C2F58-C2F56-Cl-7-OCHF26-C3F7-i6-C3F7-i6-C3F7-i | m.p.98-102.4℃nD1.5660(22.8℃)m.p.168.7-171.9℃nD1.5400(21.1℃)m.p.139-146℃m.p.198-201℃m.p.96.1-101.3℃nD1.5163(23.3℃)nD1.5211(23.3℃) |
No | R | R1 | Xn | 物理性质 |
487488489490491492493494495496497498499500501 | CH2CNCH2(3-Cl-ph)COCH2BrCOCH2OCH3CO(3-Cl-Ph)COOC2H5COOC4H9-tCOOCH3HCOC2H5HCOCH3COC2H5HH | Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2Q2 | 6-C3F7-i6-C3F7-i6-C3F7-i6-C3F7-i6-C3F7-i6-C3F7-i6-C3F7-i6-C3F7-i6-OCH(CF3)26-OCH(CF3)26-CF2CHFOCF26-CF2CHFOCF26-CF2CHFOCF26-O-(3-CF3-Ph)6-O-(3-Cl-5-CF3-2-Pyr) | m.p.109-113.1℃nD1.5329(20.6℃)nD1.4910(23.5℃)nD1.5106(21.6℃)m.p.54-58℃m.p.140-148.3℃nD1.5598(23.4℃)m.p.130-135℃m.p.137.5-139.9℃nD1.4932(23.4℃)m.p.119.8-119.9℃nD1.4 977(21.3℃)nD1.5000(24.4℃)m.p.113.8-116.0℃m.p.75-81℃ |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310073833.6A CN103288754B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP312297/1999 | 1999-11-02 | ||
JP31229799 | 1999-11-02 | ||
JP2000094493 | 2000-03-30 | ||
JP094493/2000 | 2000-03-30 |
Related Child Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2005100601733A Division CN1666983B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
CN201310073833.6A Division CN103288754B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
CNA2008100837010A Division CN101239973A (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1302801A true CN1302801A (zh) | 2001-07-11 |
CN1302801B CN1302801B (zh) | 2013-03-20 |
Family
ID=26567098
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN001368583A Expired - Fee Related CN1302801B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
CN201310073833.6A Expired - Lifetime CN103288754B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
CN2005100601733A Expired - Fee Related CN1666983B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201310073833.6A Expired - Lifetime CN103288754B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
CN2005100601733A Expired - Fee Related CN1666983B (zh) | 1999-11-02 | 2000-11-02 | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 |
Country Status (16)
Country | Link |
---|---|
US (1) | US6455535B1 (zh) |
EP (1) | EP1097932B1 (zh) |
KR (2) | KR100767229B1 (zh) |
CN (3) | CN1302801B (zh) |
AR (1) | AR032605A1 (zh) |
BR (1) | BR0005220B1 (zh) |
CO (1) | CO5221059A1 (zh) |
CZ (1) | CZ301575B6 (zh) |
DE (1) | DE60043806D1 (zh) |
EG (1) | EG22880A (zh) |
ES (1) | ES2338629T3 (zh) |
HU (1) | HU229882B1 (zh) |
ID (1) | ID27911A (zh) |
IL (1) | IL139199A (zh) |
MY (1) | MY126059A (zh) |
TW (1) | TWI252850B (zh) |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1823055B (zh) * | 2003-05-12 | 2010-11-24 | 日本农药株式会社 | 取代的氨基喹唑啉酮衍生物的制备方法、其中间体及病虫害防治剂 |
CN101600698B (zh) | 2006-09-11 | 2012-01-11 | 欧加农股份有限公司;药典有限责任公司 | 喹唑啉酮和异喹啉酮乙酰胺衍生物 |
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 |
CN102858161A (zh) * | 2010-04-27 | 2013-01-02 | 先正达参股股份有限公司 | 控制耐新烟碱的蚜虫的方法 |
WO2013075645A1 (zh) * | 2011-11-25 | 2013-05-30 | 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 |
CN103728407A (zh) * | 2014-01-20 | 2014-04-16 | 崔淑华 | 一种Pyrifluquinazon残留量的测定方法 |
CN104650038A (zh) * | 2013-11-25 | 2015-05-27 | 中国中化股份有限公司 | 6-取代吡啶基喹唑啉酮类化合物及其用途 |
CN104650036A (zh) * | 2013-11-25 | 2015-05-27 | 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 |
CN104904719A (zh) * | 2014-03-11 | 2015-09-16 | 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 |
CN105076142A (zh) * | 2014-05-08 | 2015-11-25 | 江苏龙灯化学有限公司 | 一种作物保护剂 |
CN105418590A (zh) * | 2014-09-18 | 2016-03-23 | 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 |
CN105638687A (zh) * | 2014-12-04 | 2016-06-08 | 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 |
CN105707115A (zh) * | 2014-12-04 | 2016-06-29 | 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 |
CN105707078A (zh) * | 2014-12-04 | 2016-06-29 | 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 |
CN105707111A (zh) * | 2014-12-04 | 2016-06-29 | 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 |
CN105732587A (zh) * | 2014-12-12 | 2016-07-06 | 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 |
CN105794811A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
CN105794810A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
CN105794812A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
CN105794814A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
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 |
CN110698416A (zh) * | 2019-12-16 | 2020-01-17 | 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 |
CN111533701A (zh) * | 2020-07-02 | 2020-08-14 | 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 |
CN111704604A (zh) * | 2020-08-19 | 2020-09-25 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉的制备方法 |
CN111808075A (zh) * | 2020-09-07 | 2020-10-23 | 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 |
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 |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE406348T1 (de) | 2004-09-23 | 2008-09-15 | Schering Plough Ltd | Bekämpfung von parasiten in tieren durch verwendung neuer trifluormethansulfonanilidoximetherderivate |
US8119568B2 (en) | 2007-01-26 | 2012-02-21 | Basf Se | 3-amino-1,2-benzisothiazole compounds for combating animal pest II |
MX2009007666A (es) | 2007-02-06 | 2009-07-27 | Basf Se | Mezclas de pesticidas. |
JP2010524483A (ja) | 2007-04-23 | 2010-07-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 化学物質とトランスジェニック改変とを組み合わせることによる植物生産性の増強 |
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 |
US20100311582A1 (en) | 2008-01-25 | 2010-12-09 | Syngenta Crop Protection, Inc. | Chemical compounds |
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 |
MX2011007403A (es) | 2009-01-27 | 2011-08-03 | Basf Se | Metodo para desinfectar semillas. |
WO2010089244A1 (en) | 2009-02-03 | 2010-08-12 | Basf Se | Method for dressing seeds |
US8765774B2 (en) | 2009-03-04 | 2014-07-01 | Basf Se | 3-arylquinazolin-4-one compounds for combating invertebrate pests |
EP2451804B1 (en) | 2009-07-06 | 2014-04-30 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
WO2011009804A2 (en) | 2009-07-24 | 2011-01-27 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
MX2012001170A (es) | 2009-07-30 | 2012-07-20 | Merial Ltd | Compuestos de 4-amino-tieno [2,3-d]pirimidina insecticidas y metodos para su uso. |
ES2589792T3 (es) | 2010-03-23 | 2016-11-16 | Basf Se | Compuestos de piridazina para el control de plagas de invertebrados |
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 |
AR100304A1 (es) | 2014-02-05 | 2016-09-28 | Basf Corp | Formulación de recubrimiento de semillas |
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 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0735035B1 (en) * | 1995-03-31 | 2002-06-05 | Nihon Nohyaku Co., Ltd. | Substituted aminoquinazolinone (thione) derivatives or salts thereof, intermediates thereof, and pest controllers and a method for using the same |
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 CO CO00083069A patent/CO5221059A1/es not_active Application Discontinuation
- 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 BR BRPI0005220-5A patent/BR0005220B1/pt not_active IP Right Cessation
- 2000-11-01 ID IDP20000940A patent/ID27911A/id unknown
- 2000-11-02 CN CN001368583A patent/CN1302801B/zh not_active Expired - Fee Related
- 2000-11-02 CN CN201310073833.6A patent/CN103288754B/zh not_active Expired - Lifetime
- 2000-11-02 ES ES00123887T patent/ES2338629T3/es not_active Expired - Lifetime
- 2000-11-02 CN CN2005100601733A patent/CN1666983B/zh not_active Expired - Fee Related
- 2000-11-02 EP EP00123887A patent/EP1097932B1/en not_active Expired - Lifetime
- 2000-11-02 DE DE60043806T patent/DE60043806D1/de not_active Expired - Lifetime
- 2000-11-02 KR KR1020000064784A patent/KR100767229B1/ko active IP Right Grant
-
2007
- 2007-07-25 KR KR1020070077597A patent/KR20070089108A/ko not_active Application Discontinuation
Cited By (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1823055B (zh) * | 2003-05-12 | 2010-11-24 | 日本农药株式会社 | 取代的氨基喹唑啉酮衍生物的制备方法、其中间体及病虫害防治剂 |
CN101600698B (zh) | 2006-09-11 | 2012-01-11 | 欧加农股份有限公司;药典有限责任公司 | 喹唑啉酮和异喹啉酮乙酰胺衍生物 |
CN102858161A (zh) * | 2010-04-27 | 2013-01-02 | 先正达参股股份有限公司 | 控制耐新烟碱的蚜虫的方法 |
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 |
WO2013075645A1 (zh) * | 2011-11-25 | 2013-05-30 | 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 |
CN103130771A (zh) * | 2011-11-25 | 2013-06-05 | 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 |
CN104650036A (zh) * | 2013-11-25 | 2015-05-27 | 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 |
CN104650038A (zh) * | 2013-11-25 | 2015-05-27 | 中国中化股份有限公司 | 6-取代吡啶基喹唑啉酮类化合物及其用途 |
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 |
CN103728407A (zh) * | 2014-01-20 | 2014-04-16 | 崔淑华 | 一种Pyrifluquinazon残留量的测定方法 |
CN103728407B (zh) * | 2014-01-20 | 2015-08-26 | 崔淑华 | 一种Pyrifluquinazon残留量的测定方法 |
CN104904719A (zh) * | 2014-03-11 | 2015-09-16 | 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 |
CN105076142A (zh) * | 2014-05-08 | 2015-11-25 | 江苏龙灯化学有限公司 | 一种作物保护剂 |
CN105418590A (zh) * | 2014-09-18 | 2016-03-23 | 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 |
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 |
CN105707115A (zh) * | 2014-12-04 | 2016-06-29 | 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 |
CN105707078A (zh) * | 2014-12-04 | 2016-06-29 | 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 |
CN105707111A (zh) * | 2014-12-04 | 2016-06-29 | 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 |
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 |
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 |
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 |
CN105638687A (zh) * | 2014-12-04 | 2016-06-08 | 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 |
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 |
CN105732587A (zh) * | 2014-12-12 | 2016-07-06 | 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 |
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 |
CN105794814A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
CN105794812A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
CN105794810A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
CN105794811A (zh) * | 2014-12-30 | 2016-07-27 | 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 |
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 |
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 |
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 |
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 |
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 |
CN110698416A (zh) * | 2019-12-16 | 2020-01-17 | 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 |
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 |
CN111533701A (zh) * | 2020-07-02 | 2020-08-14 | 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 |
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 |
CN111704604A (zh) * | 2020-08-19 | 2020-09-25 | 湖南速博生物技术有限公司 | 一种吡啶喹唑啉的制备方法 |
CN111808075A (zh) * | 2020-09-07 | 2020-10-23 | 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 |
Also Published As
Publication number | Publication date |
---|---|
BR0005220B1 (pt) | 2010-11-03 |
ES2338629T3 (es) | 2010-05-11 |
DE60043806D1 (de) | 2010-03-25 |
EP1097932A1 (en) | 2001-05-09 |
CN1302801B (zh) | 2013-03-20 |
CN1666983A (zh) | 2005-09-14 |
CZ20003953A3 (en) | 2001-06-13 |
IL139199A (en) | 2006-10-31 |
US6455535B1 (en) | 2002-09-24 |
KR20070089108A (ko) | 2007-08-30 |
HUP0004212A3 (en) | 2002-02-28 |
CN103288754B (zh) | 2016-03-02 |
CZ301575B6 (cs) | 2010-04-21 |
TWI252850B (en) | 2006-04-11 |
CO5221059A1 (es) | 2002-11-28 |
CN103288754A (zh) | 2013-09-11 |
KR100767229B1 (ko) | 2007-10-16 |
HUP0004212A2 (hu) | 2001-11-28 |
HU229882B1 (hu) | 2014-11-28 |
CN1666983B (zh) | 2010-05-05 |
HU0004212D0 (zh) | 2001-01-29 |
EP1097932B1 (en) | 2010-02-10 |
KR20010051394A (ko) | 2001-06-25 |
EG22880A (en) | 2003-10-30 |
ID27911A (id) | 2001-05-03 |
BR0005220A (pt) | 2001-06-19 |
AR032605A1 (es) | 2003-11-19 |
MY126059A (en) | 2006-09-29 |
IL139199A0 (en) | 2001-11-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1302801A (zh) | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,其中间体和害虫控制剂及其使用方法 | |
CN1105113C (zh) | 杀真菌嘧啶酮 | |
CN1255380C (zh) | 吡咯酰胺和吡咯硫代酰胺杀菌剂 | |
CN1221526C (zh) | 新的苯基-炔丙基醚衍生物 | |
CN1123028A (zh) | 杀真菌的稠合双环嘧啶酮类化合物 | |
CN1311778A (zh) | 稠杂环二羧酸二酰胺衍生物或其盐,应用上述物质的除草剂及其使用方法 | |
CN1869034A (zh) | 一种芳基醚类化合物及其制备与应用 | |
CN1705668A (zh) | 杂环甲酰胺衍生物 | |
CN1216534A (zh) | 杂环取代的新颖苯衍生物和除草剂 | |
CN1036195C (zh) | 稠合杂环衍生物和含有上述衍生物的农用或园艺用杀真菌剂 | |
CN1863795A (zh) | P-糖蛋白抑制剂,其制备方法和包括该抑制剂的药物组合物 | |
CN1484641A (zh) | 杀微生物的n-苯基-n-[4-(4-吡啶基-2-嘧啶-2-基)-胺衍生物 | |
CN1823055A (zh) | 取代的氨基喹唑啉酮衍生物的制备方法、其中间体及病虫害防治剂 | |
CN1324030C (zh) | 杀真菌的三唑并嘧啶、其制备方法、其在防治有害真菌中的用途和包含所述物质的试剂 | |
CN1092188C (zh) | 取代的氨基喹唑啉酮(硫酮)衍生物或其盐,中间体,和虫害控制剂及其使用方法 | |
CN1132748A (zh) | 四唑啉酮 | |
CN1649872A (zh) | 杀真菌的三唑并嘧啶、其制备方法、其在防治有害真菌中的用途以及含有所述杀真菌的三唑并嘧啶的试剂 | |
CN1313467C (zh) | 作为杀真菌剂的6-(2,6-二氟苯基)三唑并嘧啶 | |
CN1061650C (zh) | 1-环烯基四唑啉酮类 | |
CN1042690C (zh) | 含有取代的吡啶磺酰胺类化合物的除草剂 | |
CN1246118A (zh) | 色酮衍生物和含有该衍生物作为活性成分的杀菌剂的和除草剂的组合物 | |
CN1171784A (zh) | 亚氨基氧苄基丁烯酸酯,其制备和应用 | |
CN1034904C (zh) | 含环己烷衍生物的杀虫剂及其杀虫方法 | |
CN1048545A (zh) | 取代的苯并唑啉酮和啉酮衍生物,它们的制法和作为除草剂的作用 | |
CN1101345A (zh) | 具有除草作用的嘧啶衍生物,它们的生产方法及应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CI01 | Publication of corrected invention patent application |
Correction item: Priority Correct: 312297/1999 1999.11.02 JP|094493/2000 2000.03.30 JP False: 312297/1999 1999.11.02 JP Number: 12 Volume: 29 |
|
CI03 | Correction of invention patent |
Correction item: Priority Correct: 312297/1999 1999.11.02 JP|094493/2000 2000.03.30 JP False: 312297/1999 1999.11.02 JP Number: 12 Page: The title page Volume: 29 |
|
ERR | Gazette correction |
Free format text: CORRECT: PRIORITY; FROM: 312297/1999 1999.11.02 JP TO: 312297/1999 1999.11.02 JP;094493/2000 2000.03.30 JP |
|
RECT | Rectification | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130320 Termination date: 20181102 |