CN112442026B - 介离子衍生物及其制备方法和应用 - Google Patents
介离子衍生物及其制备方法和应用 Download PDFInfo
- Publication number
- CN112442026B CN112442026B CN201910795631.XA CN201910795631A CN112442026B CN 112442026 B CN112442026 B CN 112442026B CN 201910795631 A CN201910795631 A CN 201910795631A CN 112442026 B CN112442026 B CN 112442026B
- Authority
- CN
- China
- Prior art keywords
- compound
- alkyl
- preparation
- mesoionic
- compounds
- 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.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 230000002147 killing effect Effects 0.000 claims abstract description 3
- 241000500437 Plutella xylostella Species 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 241001556089 Nilaparvata lugens Species 0.000 claims description 7
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 7
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 239000000575 pesticide Substances 0.000 abstract description 22
- 241000607479 Yersinia pestis Species 0.000 abstract description 11
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 2
- -1 cyano, hydroxy Chemical group 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940051841 polyoxyethylene ether Drugs 0.000 description 10
- 229920000056 polyoxyethylene ether Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 241000254173 Coleoptera Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 241000132121 Acaridae Species 0.000 description 5
- 241000255777 Lepidoptera Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 241000238814 Orthoptera Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241001600407 Aphis <genus> Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241001414989 Thysanoptera Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241001414720 Cicadellidae Species 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241001477931 Mythimna unipuncta Species 0.000 description 3
- 241000238661 Periplaneta Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000254152 Sitophilus oryzae Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- WSMRNENBSPLEFU-UHFFFAOYSA-N n-[(2-chloro-1,3-thiazol-5-yl)methyl]pyridin-2-amine Chemical compound S1C(Cl)=NC=C1CNC1=CC=CC=N1 WSMRNENBSPLEFU-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 239000004562 water dispersible granule Substances 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- PBDOATRQTXZFOG-UHFFFAOYSA-N 2-(2-nitro-1-phenylethyl)propanedioic acid Chemical compound C1(=CC=CC=C1)C(C[N+](=O)[O-])C(C(=O)O)C(=O)O PBDOATRQTXZFOG-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- IWOUTIHKEQOMCY-UHFFFAOYSA-N 2-ethyl-3,4,5-triphenylphenol Chemical compound C1(=CC=CC=C1)C=1C(=C(C(=C(C1)O)CC)C1=CC=CC=C1)C1=CC=CC=C1 IWOUTIHKEQOMCY-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IIWPRELLGLCAGW-UHFFFAOYSA-N 6-methylsulfanylpyridine-3-carbaldehyde Chemical compound CSC1=CC=C(C=O)C=N1 IIWPRELLGLCAGW-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- 241000254124 Aleyrodidae Species 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241001279740 Anopheles sinensis Species 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241001220430 Aphelenchus Species 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- 241000256054 Culex <genus> Species 0.000 description 2
- 241000238710 Dermatophagoides Species 0.000 description 2
- 241000238713 Dermatophagoides farinae Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001251094 Formica Species 0.000 description 2
- 241000927584 Frankliniella occidentalis Species 0.000 description 2
- 241001454728 Gelechiidae Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000498254 Heterodera glycines Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001470017 Laodelphax striatella Species 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- 241000219823 Medicago Species 0.000 description 2
- 241000243786 Meloidogyne incognita Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000409991 Mythimna separata Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- DATAGRPVKZEWHA-YFKPBYRVSA-N N(5)-ethyl-L-glutamine Chemical compound CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WFAKQKIBWNVCPZ-UHFFFAOYSA-N N-[(6-methylsulfanylpyridin-3-yl)methyl]pyridin-2-amine Chemical compound CSC1=CC=C(C=N1)CNC1=NC=CC=C1 WFAKQKIBWNVCPZ-UHFFFAOYSA-N 0.000 description 2
- 241000855602 Nothotylenchus acris Species 0.000 description 2
- 241000320508 Pentatomidae Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241001439019 Phthorimaea operculella Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 241000238711 Pyroglyphidae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 241000255626 Tabanus <genus> Species 0.000 description 2
- 241000916145 Tarsonemidae Species 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000002528 anti-freeze Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QVBNGHSKLNZKJV-UHFFFAOYSA-N benzene 1-nitroethene Chemical compound [N+](=O)([O-])C=C.C1=CC=CC=C1 QVBNGHSKLNZKJV-UHFFFAOYSA-N 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- IBGOYXMLFPKRDY-UHFFFAOYSA-N dimethyl 2-(2-nitro-1-phenylethyl)propanedioate Chemical compound COC(=O)C(C(=O)OC)C(C[N+]([O-])=O)C1=CC=CC=C1 IBGOYXMLFPKRDY-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003090 pesticide formulation Substances 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ORUGTGTZBRUQIT-UHFFFAOYSA-N tert-butyl n-pyridin-2-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=N1 ORUGTGTZBRUQIT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BFBKUYFMLNOLOQ-UHFFFAOYSA-N 2-butoxyethanamine Chemical compound CCCCOCCN BFBKUYFMLNOLOQ-UHFFFAOYSA-N 0.000 description 1
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- PJHRMQPEENZCPK-UHFFFAOYSA-N 2-methylsulfanylpropan-1-amine Chemical compound CSC(C)CN PJHRMQPEENZCPK-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
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-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
- AFWWKZCPPRPDQK-UHFFFAOYSA-N 6-chloropyridine-3-carbaldehyde Chemical compound ClC1=CC=C(C=O)C=N1 AFWWKZCPPRPDQK-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- 241001619980 Acaphylla theae Species 0.000 description 1
- 241001159389 Aculops pelekassi Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000059559 Agriotes sordidus Species 0.000 description 1
- 241000993143 Agromyza Species 0.000 description 1
- 235000010167 Allium cepa var aggregatum Nutrition 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 241000857945 Anita Species 0.000 description 1
- 241001237431 Anomala Species 0.000 description 1
- 241001463392 Anoplophora macularia Species 0.000 description 1
- 241001177135 Anthrenus verbasci Species 0.000 description 1
- 241001414828 Aonidiella aurantii Species 0.000 description 1
- 241000134843 Aphelenchoides besseyi Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000952611 Aphis craccivora Species 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 241000256846 Apis cerana Species 0.000 description 1
- 241001048568 Apolygus lucorum Species 0.000 description 1
- 241000205585 Aquilegia canadensis Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241001503477 Athalia rosae Species 0.000 description 1
- 241000219307 Atriplex rosea Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241001313742 Callosobruchus chinensis Species 0.000 description 1
- 241001184747 Caloptilia theivora Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 235000007862 Capsicum baccatum Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001347511 Carposina sasakii Species 0.000 description 1
- 241001347514 Carposinidae Species 0.000 description 1
- 244000097582 Cecropia peltata Species 0.000 description 1
- 241001177891 Cheyletidae Species 0.000 description 1
- 241001279148 Cheyletus Species 0.000 description 1
- 241001279151 Cheyletus malaccensis Species 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 241001641310 Cunea Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000157278 Dacus <genus> Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241000353522 Earias insulana Species 0.000 description 1
- 241001183635 Echinocnemus Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000738498 Epitrix pubescens Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001331999 Euproctis Species 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 241000654868 Frankliniella fusca Species 0.000 description 1
- 241000365767 Frankliniella intonsa Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241001243091 Gryllotalpa Species 0.000 description 1
- 241000241125 Gryllotalpa gryllotalpa Species 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241000255990 Helicoverpa Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241000756137 Hemerocallis Species 0.000 description 1
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- 241001483218 Hydrellia griseola Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241001531327 Hyphantria cunea Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000008119 Larix laricina Nutrition 0.000 description 1
- 241000218653 Larix laricina Species 0.000 description 1
- 241001177117 Lasioderma serricorne Species 0.000 description 1
- 241000935799 Lefroyothrips lefroyi Species 0.000 description 1
- 240000004322 Lens culinaris Species 0.000 description 1
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 241000368289 Lepidosaphes ulmi Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241001520143 Liriomyza trifolii Species 0.000 description 1
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001043195 Lyctus brunneus Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- 241001190211 Lyonetia Species 0.000 description 1
- 241001190778 Lyonetiidae Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 241001599018 Melanogaster Species 0.000 description 1
- 241001608711 Melo Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000201432 Nacobbus aberrans Species 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- 241001521166 Nezara antennata Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 240000008467 Oryza sativa Japonica Group Species 0.000 description 1
- 235000005043 Oryza sativa Japonica Group Nutrition 0.000 description 1
- 241001570894 Oulema oryzae Species 0.000 description 1
- 241000382928 Oxya Species 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- 241000488585 Panonychus Species 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000721451 Pectinophora gossypiella Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241001510001 Periplaneta brunnea Species 0.000 description 1
- 241001510010 Periplaneta fuliginosa Species 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000720470 Phyllonorycter Species 0.000 description 1
- 241000437063 Phyllotreta striolata Species 0.000 description 1
- 241000255964 Pieridae Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 241000254101 Popillia japonica Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000193940 Pratylenchus penetrans Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241001466030 Psylloidea Species 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000365764 Scirtothrips dorsalis Species 0.000 description 1
- 241000545593 Scolytinae Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 241001492664 Solenopsis <angiosperm> Species 0.000 description 1
- 240000003829 Sorghum propinquum Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000532887 Sphenophorus venatus Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000270708 Testudinidae Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 235000009430 Thespesia populnea Nutrition 0.000 description 1
- 244000299492 Thespesia populnea Species 0.000 description 1
- 241000339373 Thrips palmi Species 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- 241000130767 Tineidae Species 0.000 description 1
- 241000333690 Tineola bisselliella Species 0.000 description 1
- 241000663810 Tingidae Species 0.000 description 1
- 241001271990 Tomicus piniperda Species 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241001312519 Trigonella Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 244000078534 Vaccinium myrtillus Species 0.000 description 1
- 235000010726 Vigna sinensis Nutrition 0.000 description 1
- 244000042314 Vigna unguiculata Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 241000529915 Xylophilus Species 0.000 description 1
- 241001466336 Yponomeutidae Species 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229940009868 aluminum magnesium silicate Drugs 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000021029 blackberry Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000001728 capsicum frutescens Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940095130 dimethyl capramide Drugs 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical group [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 239000004499 emulsifiable powder Substances 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940046533 house dust mites Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 208000009091 myxoma Diseases 0.000 description 1
- 125000004108 n-butyl group Chemical group [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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 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
- 239000000312 peanut oil Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004551 spreading oil Substances 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
- 239000010902 straw Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940026510 theanine Drugs 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及一种介离子衍生物及其制备方法和应用；具体地，本发明涉及式(I)所示的介离子衍生物或式(I)所示介离子衍生物的立体异构体、氮氧化物或其盐，及介离子衍生物的制备方法，及它们在农业中作为杀虫剂的用途，及其杀虫剂组合物的形式，以及用这些化合物或组合物来杀灭害虫的方法；其中，R1、R2和R3具有本发明所述的含义。
Description
技术领域
本发明涉及农药领域，具体的本发明涉及一种介离子衍生物、介离子衍生物的制备方法及其在农业中作为杀虫剂的应用。
背景技术
杂环介离子化合物作为杀虫剂是已知的，在现有技术WO09099929、WO11017334、WO11017347、WO11017342、WO12092115、WO12106495、WO12136724、WO14033244、WO14202582、WO14167084、WO16055431、WO16171053和WO17093214均有记载，而本发明涉及的介离子衍生物在现有技术中没有报道。
发明内容
本发明涉及一种新的介离子衍生物、其对农业中的害虫，特别是对小菜蛾、粘虫、桃蚜、褐飞虱等具有优异的防治效果。
具体的：
一方面，本发明提供一种新的介离子化合物，其为具有式(I)所示的化合物或具有式(I)所示化合物的立体异构体、氮氧化物或其盐：
其中：
R1为氢或C1-6烷基；
R2为5-6元杂芳基；所述的5-6元杂芳基任选地被一个或多个选自卤素、氰基、羟基、硝基、C1-6烷基、C1-6烷氧基、C1-6烷硫基、卤代C1-6烷基、卤代C1-6烷氧基或卤代C1-6烷硫基的取代基取代；
R3为C6-10芳基或5-6元杂芳基；所述的C6-10芳基和5-6元杂芳基任选地被一个或多个选自卤素、氰基、羟基、硝基、C1-6烷基、C1-6烷氧基、卤代C1-6烷基或卤代C1-6烷氧基的取代基取代。
在一些实施方案中，R1为氢或C1-4烷基。
还在一些实施方案中，R1为氢、CH3-或CH3CH2-。
在一些实施方案中，R2为噻唑基、吡啶基或嘧啶基；所述的噻唑基、吡啶基和嘧啶基任选地被一个或多个选自卤素、氰基、羟基、硝基、C1-4烷基、C1-4烷氧基、C1-4烷硫基、卤代C1-4烷基、卤代C1-4烷氧基或卤代C1-4烷硫基的取代基取代。
还在一些实施方案中，R2为噻唑-5-基、吡啶-3-基或嘧啶-5-基；所述的噻唑-5-基、吡啶-3-基和嘧啶-5-基任选地被一个或多个选自卤素、氰基、羟基、硝基、C1-4烷基、C1-4烷氧基、C1-4烷硫基、卤代C1-4烷基、卤代C1-4烷氧基或卤代C1-4烷硫基的取代基取代。
还在一些实施方案中，R2为噻唑-5-基、吡啶-3-基或嘧啶-5-基；所述的噻唑-5-基、吡啶-3-基和嘧啶-5-基任选地被一个或多个选自氟、氯、溴、碘、氰基、羟基、硝基、CH3-、CH3O-、CH3S-、CF3-或CF3O-的取代基取代。
又还在一些实施方案中，R2为
在一些实施方案中，R3为苯基或噻吩基；所述的苯基和噻吩基任选地被一个或多个选自卤素、氰基、羟基、硝基、C1-4烷基、C1-4烷氧基、卤代C1-4烷基或卤代C1-4烷氧基的取代基取代。
还在一些实施方案中，R3为苯基或噻吩基；其中所述的苯基和噻吩基任选地被一个或多个选自氟、氯、溴、碘、氰基、羟基、硝基、CH3-、CH3O-、CF3-或CF3O-的取代基取代。
又还在一些实施方案中，R3为
还在一些实施方案中，本发明涉及一种化合物，其为具有下列结构之一的化合物或具有下列之一结构化合物的立体异构体、氮氧化物或其盐：
又一方面，本发明提供一种组合物，包含至少一种本发明所述的化合物。
进一步地，本发明所述的组合物包含农药学上可接受的辅料。
另一方面，本发明提供本发明所述的化合物或本发明所述的组合物在农业中作为杀虫剂的应用。
又另一方面，本发明提供一种本发明所述的化合物或本发明所述的组合物在农业中杀灭害虫的方法。
进一步地，本发明所述的害虫包括小菜蛾、黏虫、苜蓿蚜和褐飞虱。
本发明的详细说明
定义和一般术语
现在详细描述本发明的某些实施方案，其实例由随附的结构式和化学式说明。本发明意图涵盖所有的替代、修改和等同技术方案，它们均包括在如权利要求定义的本发明范围内。本领域技术人员应认识到，许多与本发明所述类似或等同的方法和材料能够用于实践本发明。本发明绝不限于本发明所述的方法和材料。在所结合的文献、专利和类似材料的一篇或多篇与本申请不同或相矛盾的情况下(包括但不限于所定义的术语、术语应用、所描述的技术，等等)，以本申请为准。
应进一步认识到，本发明的某些特征，为清楚可见，在多个独立的实施方案中进行了描述，但也可以在单个实施例中以组合形式提供。反之，本发明的各种特征，为简洁起见，在单个实施方案中进行了描述，但也可以单独或以任意适合的子组合提供。
除非另外说明，本发明所使用的所有科技术语具有与本发明所属领域技术人员的通常理解相同的含义。本发明涉及的所有专利和公开出版物通过引用方式整体并入本发明。
除非另外说明，应当应用本发明所使用的下列定义。出于本发明的目的，化学元素与元素周期表CAS版，和《化学和物理手册》，第75版，1994一致。此外，有机化学一般原理可参考"Organic Chemistry",Thomas Sorrell,University Science Books,Sausalito:1999,和"March's Advanced Organic Chemistry"by Michael B.Smith and JerryMarch,John Wiley&Sons,New York:2007中的描述，其全部内容通过引用并入本发明。
除非另有说明或者上下文中有明显的冲突，本发明所使用的冠词“一”、“一个(种)”和“所述”旨在包括“至少一个”或“一个或多个”。因此，本发明所使用的这些冠词是指一个或多于一个(即至少一个)宾语的冠词。例如，“一组分”指一个或多个组分，即可能有多于一个的组分被考虑在所述实施方案的实施方式中采用或使用。
术语“包含”为开放式表达，即包括本发明所指明的内容，但并不排除其他方面的内容。
“立体异构体”是指具有相同化学构造，但原子或基团在空间上排列方式不同的化合物。立体异构体包括对映异构体、非对映异构体、构象异构体(旋转异构体)、几何异构体(顺/反)异构体、阻转异构体，等等。
“对映异构体”是指一个化合物的两个不能重叠但互成镜像关系的异构体。
“非对映异构体”是指有两个或多个手性中性并且其分子不互为镜像的立体异构体。非对映异构体具有不同的物理性质，如熔点、沸点、光谱性质和反应性。非对映异构体混合物可通过高分辨分析操作如电泳和色谱，例如HPLC来分离。
本发明所使用的立体化学定义和规则一般遵循S.P.Parker,Ed.,McGraw-HillDictionary of Chemical Terms(1984)McGraw-Hill Book Company,New York；andEliel,E.and Wilen,S.,“Stereochemistry of Organic Compounds”,John Wiley&Sons,Inc.,New York,1994中的描述。
许多有机化合物以光学活性形式存在，即它们具有使平面偏振光的平面发生旋转的能力。在描述光学活性化合物时，使用前缀D和L或R和S来表示分子关于其一个或多个手性中心的绝对构型。前缀d和l或(+)和(-)是用于指定化合物所致平面偏振光旋转的符号，其中(-)或l表示化合物是左旋的。前缀为(+)或d的化合物是右旋的。一种具体的立体异构体是对映异构体，这种异构体的混合物称作对映异构体混合物。对映异构体的50:50混合物称为外消旋混合物或外消旋体，当在化学反应或过程中没有立体选择性或立体特异性时，可出现这种情况。
本发明公开化合物的任何不对称原子(例如，碳等)都可以以外消旋或对映体富集的形式存在，例如(R)-、(S)-或(R,S)-构型形式存在。在某些实施方案中，各不对称原子在(R)-或(S)-构型方面具有至少50％对映体过量，至少60％对映体过量，至少70％对映体过量，至少80％对映体过量，至少90％对映体过量，至少95％对映体过量，或至少99％对映体过量。
依据起始物料和方法的选择，本发明化合物可以以可能的异构体中的一个或它们的混合物，例如外消旋体和非对应异构体混合物(这取决于不对称碳原子的数量)的形式存在。光学活性的(R)-或(S)-异构体可使用手性合成子或手性试剂制备，或使用常规技术拆分。如果化合物含有一个双键，取代基可能为E或Z构型；如果化合物中含有二取代的环烷基，环烷基的取代基可能有顺式或反式构型。
所得的任何立体异构体的混合物可以依据组分物理化学性质上的差异被分离成纯的或基本纯的几何异构体，对映异构体，非对映异构体，例如，通过色谱法和/或分步结晶法。
可以用已知的方法将任何所得终产物或中间体的外消旋体通过本领域技术人员熟悉的方法拆分成光学对映体，如，通过对获得的其非对映异构的盐进行分离。外消旋的产物也可以通过手性色谱来分离，如，使用手性吸附剂的高效液相色谱(HPLC)。特别地，对映异构体可以通过不对称合成制备。
像本发明所描述的，本发明的化合物可以任选地被一个或多个取代基所取代，如上面的通式化合物，或者像实施例里面特殊的例子，子类，和本发明所包含的一类化合物。应了解“任选取代的”这个术语与“取代或非取代的”这个术语可以交换使用。一般而言，术语“取代的”表示所给结构中的一个或多个氢原子被具体取代基所取代。除非其他方面表明，一个任选的取代基团可以在基团各个可取代的位置进行取代。当所给出的结构式中不只一个位置能被选自具体基团的一个或多个取代基所取代，那么取代基可以相同或不同地在各个位置取代。具体地，“一个或多个”的实例是指1、2、3、4、5、6、7、8、9或10个。其中所述的取代基可以是，但并不限于，氘，氟，氯，溴，碘，氰基，羟基，硝基，氨基，羧基，烷基，烷氧基，烷氧基烷基，烷氧基烷氧基，烷氧基烷氨基，芳氧基，杂芳基氧基，杂环基氧基，芳基烷氧基，杂芳基烷氧基，杂环基烷氧基，环烷基烷氧基，烷氨基，烷氨基烷基，烷氨基烷氨基，环烷基氨基，环烷基烷氨基，烷硫基，卤代烷基，卤代烷氧基，羟基取代的烷基，羟基取代的烷氨基，氰基取代的烷基，氰基取代的烷氧基，氰基取代的烷氨基，氨基取代的烷基，烷基酰基，杂烷基，环烷基，环烯基，环烷基烷基，杂环基，杂环基烷基，杂环基酰基，芳基，芳基烷基，芳氨基，杂芳基，杂芳基烷基，杂芳基氨基，酰胺基，磺酰基，氨基磺酰基等等。
另外，需要说明的是，除非以其他方式明确指出，在本发明中所采用的描述方式“各…独立地为”与“…各自独立地为”和“…独立地为”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。
在本说明书的各部分，本发明公开化合物的取代基按照基团种类或范围公开。特别指出，本发明包括这些基团种类和范围的各个成员的每一个独立的次级组合。例如，术语“C1-C6烷基”或“C1-6烷基”特别指独立公开的甲基、乙基、C3烷基、C4烷基、C5烷基和C6烷基。
本发明使用的术语“烷基”或“烷基基团”，表示含有1至20个碳原子，饱和的直链或支链一价烃基基团；其中所述烷基基团任选地被一个或多个本发明描述的取代基所取代。除非另外详细说明，烷基基团含有1-20个碳原子。在一实施方案中，烷基基团含有1-12个碳原子；在一实施方案中，烷基基团含有1-8个碳原子；在另一实施方案中，烷基基团含有1-6个碳原子；在又一实施方案中，烷基基团含有1-4个碳原子；还在一实施方案中，烷基基团含有1-3个碳原子。
烷基基团的实例包含，但并不限于，甲基(Me、-CH3)，乙基(Et、-CH2CH3)，正丙基(n-Pr、-CH2CH2CH3)，异丙基(i-Pr、-CH(CH3)2)，正丁基(n-Bu、-CH2CH2CH2CH3)，异丁基(i-Bu、-CH2CH(CH3)2)，仲丁基(s-Bu、-CH(CH3)CH2CH3)，叔丁基(t-Bu、-C(CH3)3)，正戊基(-CH2CH2CH2CH2CH3)，2-戊基(-CH(CH3)CH2CH2CH3)，3-戊基(-CH(CH2CH3)2)，2-甲基-2-丁基(-C(CH3)2CH2CH3)，3-甲基-2-丁基(-CH(CH3)CH(CH3)2)，3-甲基-1-丁基(-CH2CH2CH(CH3)2)，2-甲基-1-丁基(-CH2CH(CH3)CH2CH3)，等等。
术语“烷氧基”表示烷基基团通过氧原子与分子其余部分相连，其中烷基基团具有如本发明所述的含义。烷氧基基团的实例包括，但并不限于，甲氧基(MeO、-OCH3)，乙氧基(EtO、-OCH2CH3)，1-丙氧基(n-PrO、n-丙氧基、-OCH2CH2CH3)，2-丙氧基(i-PrO、i-丙氧基、-OCH(CH3)2)等等。
术语“烷硫基”表示烷基基团通过硫原子与分子其余部分相连，其中烷基基团具有如本发明所述的含义。烷硫基基团的实例包括，但并不限于，-SCH3、-SCH2CH3、-SCH2CH2CH3、-SCH(CH3)2等等。
术语“卤素”是指氟(F)、氯(Cl)、溴(Br)或碘(I)。
术语“杂芳基”表示含有5-12个环原子，或5-10个环原子，或5-6个环原子的单环、双环和三环体系，其中至少一个环体系是芳香族的，且至少一个环体系包含一个或多个杂原子，其中每一个环体系包含5-7个原子组成的环，且有一个或多个附着点与分子其余部分相连。术语“杂芳基”可以与术语“杂芳环”或“杂芳族化合物”交换使用。所述杂芳基基团任选地被一个或多个本发明所描述的取代基所取代。在一实施方案中，5-10个原子组成的杂芳基包含1，2，3或4个独立选自O，S和N的杂原子。
杂芳基基团的实例包括，但并不限于，呋喃-2-基，呋喃-3-基，N-咪唑基，咪唑-2-基，咪唑-4-基，咪唑-5-基，异噁唑-3-基，异噁唑-4-基，异噁唑-5-基，噁唑-2-基，噁唑4-基，噁唑-5-基，N-吡咯基，吡咯-2-基，吡咯-3-基，吡啶-2-基，吡啶-3-基，吡啶-4-基，嘧啶-2-基，嘧啶-4-基，嘧啶-5-基，哒嗪基，噻唑-2-基，噻唑-4-基，噻唑-5-基，四唑基，三唑基，噻吩-2-基，噻吩-3-基，吡唑基，异噻唑基，1,2,3-噁二唑基，1,2,5-噁二唑基，1,2,4-噁二唑基，1,2,3-三唑基，1,2,3-硫代二唑基，1,3,4-硫代二唑基，1,2,5-硫代二唑基，吡嗪基，1,3,5-三嗪基，嘧啶酮基，吡啶酮基；也包括以下的双环，但绝不限于这些双环：苯并咪唑基，苯并呋喃基，苯并四氢呋喃基，苯并噻吩基，吲哚基(如2-吲哚基)，苯并哌啶基，等等。
术语“卤代烷基”表示烷基基团被一个或多个卤素原子所取代，这样的实例包含，但并不限于，-CF3，-CHF2，-CH2Cl，-CH2CF3，-CH2CHF2，-CH2CH2CF3等。
术语“卤代烷氧基”表示烷氧基基团被一个或多个卤素原子所取代，这样的实例包含，但并不限于，-OCF3，-OCHF2，-OCHCl2，-OCH2CHF2，-OCH2CHCl2，-OCH(CH3)CHF2等。
术语“卤代烷硫基”表示烷硫基基团被一个或多个卤素原子所取代。
本发明所述化合物的盐，包括衍生自碱金属或碱土金属的那些以及衍生自氨和胺的那些。优选的阳离子包括钠、钾、镁以及具有化学式N+(RAARBBRCCRDD)的铵阳离子，其中RAA、RBB、RCC和RDD独立地选自氢、C1-C6烷基和C1-C6羟基烷基。具有式(I)的化合物的盐可以通过用金属氢氧化物(例如氢氧化钠)或胺(例如氨、三甲胺、二乙醇胺、2-甲硫基丙胺、双烯丙基胺、2-丁氧基乙胺、吗啉、环十二胺或苄胺)对具有式(I)的化合物进行处理来制备。
当本发明的化合物包含一个碱部分时，可接受的盐可以由有机酸和无机酸形成，例如乙酸、丙酸、乳酸、柠檬酸、酒石酸、琥珀酸、富马酸、马来酸、丙二酸、扁桃酸、苹果酸、邻苯二甲酸、盐酸、氢溴酸、磷酸、硝酸、硫酸、甲磺酸、萘磺酸、苯磺酸、甲苯磺酸、樟脑磺酸以及类似地已知可接受的酸。
本发明化合物的组合物和制剂
本发明的化合物一般可用作组合物或制剂中的杀虫剂活性成分，通常还包括农药学上可接受的辅料，所述的辅料为表面活性剂和/或载体等，满足农药使用要求的组分都属于本发明的范围。
所述表面活性剂可以为农药制剂领域所公知的各种表面活性剂，本发明优选为乳化剂、分散剂和润湿剂中的一种或多种。
除上述表面活性剂外的其它载体可以为农药制剂领域所公知的各种载体，包括各种硅酸盐类、碳酸盐类、硫酸盐类、氧化物类、磷酸盐类、植物载体类、合成载体类。具体地，例如：白炭黑、高岭土、硅藻土、粘土、滑石、有机膨润土、浮石、二氧化钛、糊精、纤维素粉、轻质碳酸钙、可溶性淀粉、玉米淀粉、锯末粉、尿素、胺肥、尿素和胺肥的混合物、葡萄糖、麦芽糖、蔗糖、无水碳酸钾、无水碳酸钠、无水碳酸氢钾、无水碳酸氢钠、凹凸棒土、无水碳酸钾与无水碳酸氢钾的混合物和无水碳酸钠与无水碳酸氢钠的混合物中的一种或多种。
所述乳化剂可以为农药制剂领域所公知的各种乳化剂，具体地，所述乳化剂为十二烷基苯磺酸钙、三苯乙基酚聚氧乙烯醚磷酸酯、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、烷基酚聚氧乙烯聚氧丙烯醚、脂肪胺、脂肪酰胺的环氧乙烷加成物、脂肪酸聚氧乙烯酯、松香酸环氧乙烷加成物、多元醇脂肪酸酯及其环氧乙烷加成物、苯乙烯基苯基聚氧乙烯醚、烷基酚甲醛树脂聚氧乙烯醚、端羟基聚氧乙烯聚氧丙烯醚、苯乙烯基苯酚甲醛树脂聚氧乙烯聚氧丙烯醚和蓖麻油聚氧乙烯醚中的一种或多种。
所述分散剂可以为农药制剂领域所公知的各种分散剂，具体地，所述分散剂为丙烯酸均聚物钠盐、马来酸二钠盐、萘磺酸甲醛缩合物钠盐、松香嵌段聚氧乙烯醚聚氧丙烯醚磺酸盐、端羟基聚氧乙烯聚氧丙烯醚嵌段共聚物、三苯乙基酚聚氧乙烯醚磷酸酯、脂肪醇聚氧乙烯醚磷酸酯和对羟苯基木质素磺酸钠盐中的一种或多种。
所述润湿剂为农药制剂领域所公知的各种润湿剂，具体地，所述润湿剂为十二烷基硫酸钠、仲烷基硫酸钠、十二烷基苯磺酸钠、脂肪醇聚氧乙烯醚、烷基萘磺酸盐、烷基酚树脂聚氧乙烯醚硫酸盐中的一种或多种。
根据本发明的杀虫剂组合物，该杀虫剂组合物还可以含有农药制剂领域所常用的各种制剂用助剂，具体地，所述助剂为溶剂、助溶剂、增稠剂、防冻剂、囊材、保护剂、消泡剂、崩解剂、稳定剂、防腐剂和粘结剂中的一种或多种。
所述溶剂为农药制剂领域所公知的各种溶剂，具体地，所述溶剂为有机溶剂、植物油、矿物油、溶剂油和水中的一种或多种。
其中，所述有机溶剂包括N-甲基吡咯烷酮、四氢呋喃、二甲基亚砜、N,N-二甲基癸酰胺、N,N-二甲基甲酰胺、三甲苯、四甲苯、二甲苯、甲苯、辛烷、庚烷、甲醇，异丙醇、正丁醇、四氢糠醇、磷酸三丁酯、1,4-二氧六环和环己酮中的一种或多种。
所述植物油包括甲基化植物油，松脂基植物油，松节油，环氧大豆油、大豆油、花生油、菜籽油、蓖麻油、玉米油和松籽油中的一种或多种。
所述矿物油包括液蜡、机油、煤油和润滑油中的一种或多种。
同时，上述溶剂也可以作为助溶剂使用。
所述防冻剂为农药制剂领域所公知的各种防冻剂，本发明优选为乙二醇、丙二醇、甘油和尿素中的一种或多种。
所述增稠剂为农药制剂领域所公知的各种增稠剂，具体地，所述增稠剂为黄原胶、聚乙烯醇、聚丙烯醇、聚乙二醇、白炭黑、硅藻土、高岭土、粘土、海藻酸钠、硅酸铝镁、硅酸铝钠、羧甲基纤维素、羟丙基纤维素钠和有机膨润土中的一种或多种。
所述囊材为农药制剂领域所公知的各种囊材，本发明优选为聚氨酯、聚脲和脲醛树脂中的一种或多种。
所述保护剂为农药制剂领域所公知的各种保护剂，本发明优选为聚乙烯醇和/或聚乙二醇。
所述消泡剂为农药制剂领域所公知的各种消泡剂，本发明优选为有机硅氧烷、磷酸三丁酯和硅酮中的一种或多种。
所述稳定剂选自亚磷酸三苯酯、环氧氯丙烷和醋酐中的一种或多种。
所述防腐剂选自苯甲酸、苯甲酸钠、1,2-苯并异噻唑啉-3-酮(简称BIT)、卡松和山梨酸钾中的一种或多种。
本发明还提供一种由上述杀虫剂组合物所制备的制剂，所述制剂的剂型为乳油、水乳剂、微乳剂、可溶性液剂、水悬浮剂、悬乳剂、超低容量喷雾剂、油悬浮剂、微囊悬浮剂、水面展膜油剂、可湿性粉剂、水分散性颗粒剂、干悬浮剂、可溶性粉剂、可溶性粒剂、可乳化粉剂、可乳化颗粒剂、颗粒剂、固体微胶囊制剂、泡腾片剂、泡腾颗粒剂、水漂浮分散颗粒剂或种衣剂。所述剂型均可由本领域的常规方法来制备。
所述乳油制剂的制备方法例如可以包括将各活性组分、溶剂、助溶剂及乳化剂混合搅拌使其形成均匀透明油相，即可得到乳油制剂。
所述水乳剂制备方法例如可以包括将活性成分、乳化剂、助溶剂和溶剂混合，使其成为均匀油相；将水、增稠剂、防冻剂等混合，使其成均一水相。在高速剪切下，将水相加入到油相或将油相加入到水相，形成分散性良好的水乳剂。
所述微乳剂的制备方法例如可以是将活性成分，乳化剂，溶剂混合搅拌成均一透明的油相。在搅拌的条件下，逐渐的加入水，使其形成均一透明的微乳液。
所述水/油悬浮剂的制备方法：例如可以是以水或油为介质，将活性组分、表面活性剂等助剂加入砂磨釜中，进行研磨至一定粒径后，过滤。再将计量好的增稠剂加入到研磨好的母液中，剪切分散均匀。制成油悬浮剂或水悬浮剂。
所述水分散性粒剂及可溶性粒剂的制备方法：例如可以是将各活性组分、分散剂、润湿剂、载体等混合均匀，然后通过气流粉碎至一定粒径，再加入水进行捏合，最后加入造粒机中进行造粒，干燥后即可得到水分散性粒剂或可溶性粒剂。
所述可溶性粉剂及可湿性粉剂的制备方法：例如可以是将各活性组分、各种助剂及其他载体等填料充分混合，用超细粉碎机粉碎。
本发明的杀虫剂组合物可以以成品制剂形式提供，即组合物中各物质已经混合；也可以以单独制剂形式提供，使用前在桶或罐中自行混合，并根据所需活性物质的浓度选择性地与水混合进行稀释即可。
与制剂领域相关的其他信息，参见T.S.Woods的“The Formulator’s Toolbox-Product Forms for Modern Agriculture”，Pesticide Chemistry and Bioscience，TheFood-Environment Challenge，T.Brooks和T.R.Roberts编辑，Proceedings of the 9thInternational Congress on Pesticide Chemistry，The Royal Society of Chemistry，Cambridge，1999，第120-133页。还可参见U.S.3,235,361第6栏，第16行至第7栏，第19行和实施例10-41；U.S3,309,192第5栏，第43行至第7栏，第62行和实施例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182；U.S.2,891,855第3栏，第66行至第5栏，第17行和实施例1-4；Klingman的Weed Control as a Science，John Wiley and Sons，Inc.，New York，1961，第81-96页；Hance等人的Weed Control Handbook，第8版，BlackwellScientific Publications，Oxford，1989；以及Developments in formulationtechnology，PJB Publications，Richmond，UK，2000。
本发明化合物及组合物的应用
本发明化合物尤其适合防治有用植物中的动物害虫如节肢动物、腹足动物和线虫，包括但不限于：
半翅目(Hemiptera)：飞虱(飞虱科(Delphacidae))如褐飞虱(Nilaparvatalugens)、小灰飞虱(Laodelphax striatellus)；叶蝉(角顶叶蝉科(Deltocephalidae))如绿稻叶蝉(黑尾叶蝉(Nephotettix cincticeps))；蚜虫(蚜科(Aphididae))如棉蚜(Aphisgossypii)、苜蓿蚜(Aphis craccivora Koch)；蝽科(Pentatomidae)如花角绿蝽(Nezaraantennata)；粉虱(Aleyrodidae)如温室粉虱(Trialeurodes vaporariorum)；蚧(Coccidae)如加州红蚌质蚧(Calformia red scale)(Aonidiella aurantii)；网蝽科(Tingidae)；木虱(Homoptera，Psyllidea)；
鳞翅目(Lepidoptera)：螟蛾(Pyralidae)如二化螟(Chilo suppressalis)；夜蛾(Noctuidae)如斜纹贪夜蛾(Spodoptera litura)、粘虫(Pseudaletia separata)、实夜蛾属(Heliothis spp.)和铃夜蛾属(Helicoverpa spp.)；粉蝶(Pieridae)如菜粉蝶(Pierisrapae)；卷蛾(Tortricidae)如褐带卷蛾属(Adoxophyes)；细蛾(Gracillariidae)如茶细蛾(Caloptilia theivora)和苹果细蛾(Phyllonorycter ringoneella)；蛀果蛾(Carposinidae)如桃蛀果蛾(Carposina niponensis)；潜蛾(Lyonetiidae)如潜蛾属(Lyonetia spp.)；毒蛾(Lymantriidae)如毒蛾属(Lymantria spp.)和黄毒蛾属(Euproctis spp.)；巢蛾(Yponomeutidae)如小菜蛾(Plutella xylostella)；麦蛾(Gelechiidae)如红铃麦蛾(Pectinophora gossypiella)和马铃薯麦蛾(Phthorimaeaoperculella)；灯蛾(Arctiidae)如美国白蛾(Hyphantria cunea)；以及谷蛾(Tineidae)如衣蛾(Tineatranslucens)和幕谷蛾(Tineola bisselliella)；
缨翅目(Thysanoptera)：西花蓟马(Frankliniella occidentalis)、棕榈蓟马(Thrips palmi)、黄色硬蓟马(Scirtothrips dorsalis)、烟蓟马(Thrips tabaci)、丽花蓟马(Frankliniella intonsa)和马铃薯蓟马(Frankliniella fusca)；
双翅目(Diptera)：家蝇(Musca domestica)、淡色库蚊(Culex popienspallens)、三膝虻(Tabanus trigonus)、葱蝇(Hylemya anitqua)、灰地种蝇(Hylemyaplatura)、中华按蚊(Anopheles sinensis)、日本稻潜蝇(Agromyza oryzae)、稻潜蝇(Hydrellia griseola)、稻秆蝇(Chlorops oryzae)、瓜寡鬃实蝇(Dacus cucurbitae)、地中海果实蝇(Ceratitis capitata)和三叶草斑潜蝇(Liriomyza trifolii)；
鞘翅目(Coleoptera)：茄二十八星瓢虫(Epilachna vigintioctopunctata)、黄曲条菜跳甲(Phyllotreta striolata)、水稻负泥虫(Oulema oryzae)、稻象(Echinocnemussquameus)、稻水象(Lissorhoptrus oryzophilus)、棉铃象(Anthonomus grandis)、绿豆象(Callosobruchus chinensis)、寄生谷象(Sphenophorus venatus)、日本弧丽金龟(Popillia japonica)、古铜异丽金龟(Anomala cuprea)、根萤叶甲属(Diabrotica spp.)、马铃薯叶甲(Leptinotarsa decemlineata)、叩甲属(Agriotes spp.)、烟草窃蠹(Lasioderma serricorne)、小圆皮蠹(Anthrenus verbasci)、赤拟谷盗(Triboliumcastaneum)、褐粉蠹(Lyctus brunneus)、白斑星天牛(Anoplophora malasiaca)和纵坑切梢小蠹(Tomicus piniperda)；
直翅目(Orthoptera)：东亚飞蝗(Locusta migratoria)、非洲蝼蛄(Gryllotalpaafficana)、北海道稻蝗(Oxya yezoensis)和日本稻蝗(Oxya japanica)；
膜翅目(Hymenoptera)：新疆菜叶蜂(Athalia rosae)、切叶蚁属(Acromyrmexspp.)和火蚁属(Solenopsis spp.)；
线虫(Nematodes)：水稻干尖线虫(Aphelenchoides besseyi)、草莓芽线虫(Nothotylenchus acris)、大豆孢囊线虫(Heterodera glycines)、南方根结线虫(Meloidogyne incognita)、短体线虫属(Pratylenchus penetrans)和异常珍珠线虫(Nacobbus aberrans)；
蜚蠊目(Blattariae)：德国小蠊(Blattella germanica)、黑胸大蠊(Periplanetafuliginosa)、美洲大蠊(Periplaneta Americana)、褐斑大蠊(Periplaneta brunnea)和东方蜚蠊(Blatta orientalis)；
蜱螨目(Acarina)：叶螨科(Tetranychidae)(例如，朱砂叶螨(Tetranychuscinnabarinus)、二斑叶螨(Tetranychusurticae)、柑橘全爪螨(Panonychus citri)和小爪螨属(Oligonychus spp.))；瘿螨科(Eriophyidae)(例如，橘刺皮瘿螨(Aculopspelekassi))；跗线螨科(Tarsonemidae)；细须螨科(Tenuipalpidae)；杜克螨科(Tuckerellidae)；粉螨科(Tuckerellidae Acaridae)；麦食螨科(Pyroglyphidae)(例如，粉尘螨(Dermatophagoides farinae)和屋尘螨(Dermatophagoides ptrenyssnus))；肉食螨科(Cheyletidae)、马六甲肉食螨(Cheyletus malaccensis)和马六甲肉食螨(Cheyletusmoorei)；以及皮刺螨科(Dermanyssidae)。
在本发明的范围内，有用植物包括以下植物种类：谷物(小麦、大麦、黑麦、燕麦、稻、玉米、高粱以及相关物种)；甜菜(糖萝卜以及饲用甜菜)；梨果、核果以及软水果(苹果、梨、李子、桃、扁桃、樱桃、草莓、覆盆子和黑莓)；豆科植物(扁豆、宾豆、豌豆、大豆)；油料作物(油菜、芥菜、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生或大豆)；瓜类植物(南瓜、黄瓜、甜瓜)；纤维植物(棉花、亚麻、大麻、黄麻)；柑橘属水果(桔子、柠檬、葡萄柚、柑橘)；蔬菜(菠菜、莴苣、芦笋、甘蓝、胡萝卜、洋葱、番茄、马铃薯、红椒)；月桂类植物(鳄梨、樟属、樟脑)或植物，例如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、啤酒花、香蕉以及天然橡胶植物，连同草皮、观赏和森林植物，例如花卉、灌木、阔叶树或常绿树，例如针叶树，以及植物繁殖材料。
术语“植物繁殖材料”应当被理解为表示该植物的生殖部分，例如种子，这些部分可以用于该植物的繁殖，以及营养性材料，例如插条或块茎(例如马铃薯)。
本发明的化合物或组合物通过有效量的活性物质可杀灭害虫。其中，式(I)化合物的有效量在每公顷10g-5kg内时，防治害虫的效果较佳。
本发明还涉及用于防治害虫的方法，所述方法通过将本发明的活性成分或组合物施用于种子、植物或植物部位、果实或植物生长的土壤进行。施用可以在种子、植物或植物部位、果实或植物生长的土壤被害虫侵染之前和之后进行。
所用术语“有效量”表示足以在栽培植物上或在材料保护中防治害虫且不对被处理植物引起显著损害的量的本发明化合物或组合物。该量可以在宽范围内变化且取决于各种因素如害虫品种、被处理的栽培植物或材料、气候条件以及所用具体化合物。
本发明化合物或组合物使用方法简单，将本发明化合物或组合物施于所述的害虫或其生长介质上。本发明化合物或组合物的施用剂量根据天气条件、剂型、施用时机、施用方法、施用面积、目标病害、目标作物等变化。
一般合成过程
下述方案描述本发明化合物的制备。除非有进一步的说明，本发明的化合物可以通过本发明所描述的方法制备得到。制备本发明的化合物所使用的原料、试剂等等均是可以商购的，或者可以通过本领域常规的方法制备得到。在本说明书中，如果在化学名称和化学结构间存在任何差异，结构是占优的。在一些实施方案中，如无特别标明，本发明所述的室温为0-35℃。还在一些实施方案中，所述的DMF为N,N-二甲基甲酰胺。
本发明核磁共振氢谱的测试条件是：室温条件下，布鲁克(Bruker)400MHz或600MHz的核磁仪，以CDC13，d6-DMSO，CD3OD或d6-丙酮为溶剂(报导以ppm为单位)，用TMS(0ppm)或氯仿(7.26ppm)作为参照标准。当出现多重峰的时候，将使用下面的缩写：s(singlet，单峰)，d(doublet，双峰)，t(triplet，三重峰)，q(quartet，四重峰)，m(multiplet，多重峰)，br(broadened，宽峰)，dd(doublet of doublets，双二重峰)，dt(doublet of triplets，双三重峰)。偶合常数，用赫兹(Hz)表示。
本发明所用质谱测试条件为：低分辨率质谱(MS)数据测定的条件是：Agilent6120Quadrupole HPLC-MS(柱子型号：Zorbax SB-C18,2.1x 30mm,3.5μm,6min,流速为0.6mL/min，流动相：5％-95％(含0.1％甲酸的CH3CN)在(含0.1％甲酸的H2O)中的比例))，在210/254nm用UV检测，用电喷雾电离模式(ESI)。
合成方案
目标化合物I可以通过上述合成方案制备得到。中间体A化合物与中间体B化合物在加热(80～160℃)条件下反应得到目标化合物I；
其中R1、R2和R3具有本发明所述的含义。
实施例
中间体1：N-((2-氯噻唑-5-基)甲基)吡啶-2-胺的合成
第一步：吡啶-2-基氨基甲酸叔丁基酯的合成
将2-氨基吡啶(4.70g,0.05mol)，Boc酸酐(14.17g,0.65mol)和三乙胺(7.55g,75mmol)依次加入到二氯甲烷(47mL)中，在室温下搅拌反应12小时；过滤，将溶剂旋干，加水(45mL)，乙酸乙酯萃取(50mL x 3)，合并有机相，用饱和食盐水(30mL x 3)洗涤有机相，干燥，过滤，浓缩滤液，残留物经硅胶柱层析分离[石油醚/乙酸乙酯(v/v)＝5/1]，得到标题化合物(白色固体,2.31g,收率:24％)。
第二步：N-((2-氯噻唑-5-基)甲基)吡啶-2-胺的合成
室温下，将吡啶-2-基氨基甲酸叔丁酯(1.94g,0.01mol)溶于DMF(30mL)中，在0℃下，在30分钟内分批加入氢化钠(0.36g,15mmol)，加完后0℃下继续搅拌反应30分钟后，将反应温度升到室温，慢慢滴入2-氯-5-氯甲基噻唑(1.68g,0.01mol)的DMF(10mL)溶液，然后在室温下反应8小时。向反应液中加入25mL冰水，乙酸乙酯(40mL x 3)萃取，合并有机相，有机相经饱和食盐水(20mL x 3)洗涤，硫酸镁干燥，过滤，浓缩，得到油状物。将上述得到的油状物，溶于二氯甲烷(20mL)中，并在室温下慢慢滴入三氟乙酸(2.3g,0.01mol)，滴加完毕后将反应升至40℃，回流反应8小时后；将反应浓缩，加入碳酸钾水溶液，调节pH＝8，乙酸乙酯(30mL x 3)萃取，有机相水(10mL x 3)洗后，干燥，过滤，浓缩滤液，残留物经硅胶柱层析分离[石油醚/乙酸乙酯(v/v)＝7/3]，得到标题化合物(黄色油状物,0.78g,收率:34％)。
1H NMR(400MHz,CDCl3)δ(ppm):8.19(d,1H),7.45-7.42(m,2H),7.65(t,1H),6.42(d,1H),4.80(s,1H),4.68(d,2H)；
MS(ES-API,pos.ion)m/z:226.10[M+1]+。
采用相应的起始物料，根据上述中间体1的合成方法，可以制备得到表1中的中间体化合物。
表1
中间体4：N-((6-(甲硫基)吡啶-3-基)甲基)吡啶-2-胺的合成
第一步：6-(甲硫基)吡啶-3-甲醛的合成
将6-氯烟醛(7.05g,50.00mmol)、甲硫醇钠(17.5g,250mmol)和DMF(100mL)加入到250mL单口瓶，70℃油浴加热回流，搅拌12小时。待反应完毕，停止反应，冷却到室温后，倒入到冰水中(300mL)，常温下激烈搅拌10分钟。溶液中有沉淀析出，过滤出沉淀，用50mL水洗涤，得到标题化合物(米白色固体,4.8g,收率:62.7％)。
第二步：N-((6-(甲硫基)吡啶-3-基)甲基)吡啶-2-胺的合成
将6-(甲硫基)吡啶-3-甲醛(2.4g,16.00mmol)、邻氨基吡啶(1.5g,16.00mmol)和二氯甲烷(20mL)加入到100mL单口瓶，室温搅拌10分钟，减压蒸馏浓缩反应液，残余液置于90℃油浴加热，同时抽真空搅拌反应4小时。反应完成后，加入四氢呋喃(10mL)和甲醇(20mL)溶解，室温搅拌均匀，而后慢慢在30分钟内分批加入硼氢化钠(608mg,16.00mmol)，加入完成后，室温搅拌反应12小时。减压蒸馏浓缩反应液，加入水洗涤(100mL)，乙酸乙酯萃取(100mL x 3)，合并有机相，无水硫酸镁干燥有机相1小时。过滤，减压蒸馏滤液，而后柱层析分离[石油醚/乙酸乙酯(v/v)＝2/1]，得到标题化合物(白色固体,2g,收率:54％)。
1H NMR(400MHz,CDCl3)δ(ppm):8.58(s,1H),8.24(d,J＝7.3Hz,1H),7.85-7.65(m,2H),7.42(s,1H),7.13(dd,J＝7.3Hz,4.6Hz,1H),6.62(s,1H),4.36(s,2H),4.0(s,1H),2.55(s,3H)；
MS(ES-API,pos.ion)m/z:232.30[M+1]+。
采用相应的起始物料，根据上述中间体4的合成方法，可以制备得到表2中的中间体化合物。
表2
中间体8：2-(2-硝基-1-苯基乙基)丙二酸二(2,4,6-三氯苯基)酯的合成
第一步：(2-硝基乙烯)苯的合成
将苯甲醛(4.24g,40mmol)和硝基甲烷(7.32g,120mmol)溶于甲醇(8mL)中，在-8℃下，滴加10mL含量为48％的氢氧化钠(4.80g,120mmol)水溶液，控制温度在15℃以下，滴加完毕反应15分钟，沉淀生成。加入50mL冰水，0℃反应20分钟；慢慢将反应液加入到的盐酸(6M,30mL)中，控制温度在0℃并搅拌5分钟，生成黄色沉淀；抽滤，滤饼用冰水(20mL x 2)洗涤，干燥,得到标题化合物(黄色固体,3.38g,收率:57％)。
第二步：2-(2-硝基-1-苯基乙基)丙二酸二甲酯的合成
将(2-硝基乙烯)苯(3.28g,22mmol)和丙二酸二甲酯(1.64g,11mmol)溶于甲苯(20mL)中，加入三乙胺(2.22g,22mmol)，室温反应8小时。向反应液中加入50mL水，搅拌，乙酸乙酯(30mL x 2)萃取，有机相用无水硫酸钠干燥，过滤，浓缩滤液，残留物经硅胶柱层析分离[石油醚/乙酸乙酯(v/v)＝4/1]，得到标题化合物(黄色油状物,3.56g,收率:58％)。
第三步：2-(2-硝基-1-苯基乙基)丙二酸的合成
将氢氧化钠(1.60g,40mmol)溶于10mL水中，加入2-(2-硝基-1-苯基乙基)丙二酸二甲酯(1.41g,5mmol)的甲醇(10mL)溶液，将反应温度升至60℃，搅拌反应2小时。冷却至室温，将反应液倒入到冰水(20mL)中，搅拌，用稀盐酸调节pH＝1，有不溶物生成，乙酸乙酯(30mL x 2)萃取，有机相合并后旋蒸，干燥，得到标题化合物(黄色固体,1.09g,收率:86％)。
第四步：2-(2-硝基-1-苯基乙基)丙二酸二(2,4,6-三氯苯基)酯的合成
将2-(2-硝基-1-苯基乙基)丙二酸(1.26g,5mmol)溶于20mL的二氯甲烷中，滴入0.2mL DMF，将反应温度降至-5℃，慢慢滴入草酰氯(1.27g,10mmol)，滴加完毕0℃反应10小时。向反应液加入2,4,6-三氯苯酚(0.39g,2mmol)，0℃继续搅拌反应12小时。将反应液浓缩后，冷却至室温，加入甲醇(15mL)，沉淀析出，过滤，滤饼用甲醇(10mL x 2)洗涤后，干燥，得到标题化合物(白色固体,1.06g,收率:35％)。
1H NMR(400MHz,CDCl3)δ(ppm):7.40(s,4H),7.38-7.26(m,3H),7.18(t,J＝7.3Hz,2H),5.24(dd,J＝13.4,9.8Hz,1H),5.07(dd,J＝13.5,3.8Hz,1H),4.73(d,J＝8.7Hz,1H),4.55(td,J＝9.2,3.8Hz,1H)；
MS(ES-API,pos.ion)m/z:612.87[M+1]+。
采用相应的起始物料，根据上述中间体8的合成方法，可以制备得到表3中的中间体化合物。
表3
实施例1：1-((2-氯噻唑-5-基)甲基)-3-(2-硝基-1-苯基乙基)-4-氧代-4H-吡啶并[1,2-a]嘧啶-1-鎓-2-醇盐的合成
将N-((2-氯噻唑-5-基)甲基)吡啶-2-胺(0.24g,0.5mmol)和2-(2-硝基-1-苯基乙基)丙二酸二(2,4,6-三氯苯基)酯(0.31g,0.5mmol)溶于15mL甲苯溶液中，110℃反应12小时。停止反应，反应液浓缩后，经硅胶柱层析分离[石油醚/乙酸乙酯(v/v)＝1/3]，得到目标化合物(黄色固体,0.120g,收率:54％)。
MS(ES-API,pos.ion)m/z:442.9[M+1]+；
1H NMR(400MHz,CDCl3)δ(ppm):9.08(d,J＝7.1Hz,1H),7.88–7.79(m,1H),7.63(s,1H),7.57(d,J＝8.8Hz,1H),7.47(d,J＝7.2Hz,2H),7.32–7.29(m,1H),7.28–7.16(m,3H),5.63(s,2H),5.61–5.57(m,1H),5.32–5.24(m,1H),5.21–5.16(m,1H).
将中间体化合物1至7分别与相应的中间体化合物8至11经过实施例1的类似制备方法进行制备，即可得到表4中的目标化合物。
表4
测试例
1)供试靶标：小菜蛾
浸叶法：将适量甘蓝叶片在配好的药液中充分浸润后自然阴干，放入垫有滤纸的培养皿中，接小菜蛾2-3龄中期幼虫10头/皿，置于24～27℃观察室内培养，3d后调查结果。以毛笔触动虫体，无反应视为死虫，试验浓度200mg/L。
2)供试靶标：粘虫
浸叶法：将适量玉米叶片在配好的药液中充分浸润后自然阴干，放入垫有滤纸的培养皿中，接粘虫3龄中期幼虫10头/皿，置于24～27℃观察室内培养，72h后调查结果，试验浓度200mg/L。
3)供试靶标：苜蓿蚜
喷雾法：选取生长一致的豇豆叶片，用打孔器做成叶碟，每皿两个叶碟，在培养皿里放置湿海绵块，海绵上放叶碟，加水与叶碟齐平，备用。将室内饲养的2-3龄苜蓿蚜接种到准备好的叶碟上，每碟15头以上。采用喷雾塔进行处理，每处理喷药液量为0.5mL。药剂处理后的试材置于观察室，48h后观察结果。以毛笔触动虫体，无反应视为死虫，试验浓度200mg/L。
4)供试靶标：褐飞虱2-3龄
茎叶喷雾法：选择带根健康植株(稻苗2-3叶期)，根部小心洗净，植株用石英砂固定在培养皿里，将水稻苗于Potter喷雾塔下不同浓度药剂的喷雾处理，晾干接虫于植株上，盖上塑料杯。先处理空白对照，然后按试验剂量顺序重复上述操作，每处理不少于2个重复。每个处理苗为5根左右，虫为15头。药剂处理后的试材置于观察室，定时给培养皿滴水保湿，96h后观察结果。以毛笔触动虫体，无反应视为死虫，试验浓度200mg/L。
试验结果显示：在200mg/L浓度下，实施例5、实施例12、实施例14和实施例18对小菜蛾的致死率在90％以上；
在200mg/L浓度下，实施例11和实施例14对桃蚜的致死率在80％以上；
在200mg/L浓度下，实施例4和实施例9对褐飞虱的致死率为100％。
以上详细描述了本发明的优选实施方式，但是，本发明并不限于上述实施方式中的具体细节，在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，这些简单变型均属于本发明的保护范围。
Claims (7)
1.一种化合物，其为具有式(I)所示的化合物或具有式(I)所示化合物的盐：
其中：
R1为氢或CH3-；
R2为噻唑-5-基、吡啶-3-基或嘧啶-5-基；其中所述的噻唑-5-基、吡啶-3-基和嘧啶-5-基任选地被一个或多个选自氟、氯、溴、碘或CH3S-的取代基取代；
R3为苯基或噻吩基；其中所述的苯基和噻吩基任选地被一个或多个选自氟、氯、溴、碘或CF3-的取代基取代。
2.根据权利要求1所述的化合物，其中：
R2为
3.根据权利要求1所述的化合物，其中：
R3为
4.根据权利要求1-3任意一项所述的化合物，其为具有下列结构之一的化合物或具有下列之一结构化合物的盐：
5.一种组合物，包含权利要求1-4任意一项所述的化合物。
6.权利要求1-4任意一项所述的化合物或权利要求5所述的组合物在农业中作为杀虫剂的应用。
7.一种权利要求1-4任意一项所述的化合物或权利要求5所述的组合物在农业中杀灭小菜蛾和/或褐飞虱的方法。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910795631.XA CN112442026B (zh) | 2019-08-27 | 2019-08-27 | 介离子衍生物及其制备方法和应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910795631.XA CN112442026B (zh) | 2019-08-27 | 2019-08-27 | 介离子衍生物及其制备方法和应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112442026A CN112442026A (zh) | 2021-03-05 |
| CN112442026B true CN112442026B (zh) | 2023-08-08 |
Family
ID=74740937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910795631.XA Active CN112442026B (zh) | 2019-08-27 | 2019-08-27 | 介离子衍生物及其制备方法和应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112442026B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113651811B (zh) * | 2021-08-12 | 2022-06-07 | 贵州大学 | 一种含异噁唑的吡啶并嘧啶酮类化合物及其制备方法和用途 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102548973A (zh) * | 2009-08-05 | 2012-07-04 | 杜邦公司 | 介离子杀虫剂 |
| CN102574815A (zh) * | 2009-08-05 | 2012-07-11 | 杜邦公司 | 介离子杀虫剂 |
| CN102665415A (zh) * | 2009-08-05 | 2012-09-12 | 杜邦公司 | 介离子杀虫剂混合物 |
| CN102686570A (zh) * | 2009-08-05 | 2012-09-19 | 杜邦公司 | 介离子杀虫剂 |
| CN103459387A (zh) * | 2010-12-29 | 2013-12-18 | 杜邦公司 | 介离子吡啶并[1,2-a]嘧啶杀虫剂 |
| CN104311554A (zh) * | 2008-02-06 | 2015-01-28 | 纳幕尔杜邦公司 | 介离子杀虫剂 |
| WO2019086474A1 (en) * | 2017-10-31 | 2019-05-09 | Syngenta Participations Ag | Pesticidally active mesoionics heterocyclic compounds |
-
2019
- 2019-08-27 CN CN201910795631.XA patent/CN112442026B/zh active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104311554A (zh) * | 2008-02-06 | 2015-01-28 | 纳幕尔杜邦公司 | 介离子杀虫剂 |
| CN102548973A (zh) * | 2009-08-05 | 2012-07-04 | 杜邦公司 | 介离子杀虫剂 |
| CN102574815A (zh) * | 2009-08-05 | 2012-07-11 | 杜邦公司 | 介离子杀虫剂 |
| CN102665415A (zh) * | 2009-08-05 | 2012-09-12 | 杜邦公司 | 介离子杀虫剂混合物 |
| CN102686570A (zh) * | 2009-08-05 | 2012-09-19 | 杜邦公司 | 介离子杀虫剂 |
| CN104356130A (zh) * | 2009-08-05 | 2015-02-18 | 杜邦公司 | 介离子杀虫剂 |
| CN103459387A (zh) * | 2010-12-29 | 2013-12-18 | 杜邦公司 | 介离子吡啶并[1,2-a]嘧啶杀虫剂 |
| WO2019086474A1 (en) * | 2017-10-31 | 2019-05-09 | Syngenta Participations Ag | Pesticidally active mesoionics heterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112442026A (zh) | 2021-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2451681C2 (ru) | Способ получения амидного соединения | |
| TW201350019A (zh) | 醛化合物 | |
| CN110437144B (zh) | 喹啉类衍生物及其制备方法和用途 | |
| HUE026537T2 (en) | Substituted enaminocarbonyl compounds used as insecticides | |
| MX2014007458A (es) | Derivados de estrigolactama como compuestos que regulan el crecimiento de plantas. | |
| CN111153900B (zh) | 嘧啶鎓化合物及其制备方法和用途 | |
| CN114573547A (zh) | 酰胺衍生物及其制备方法和应用 | |
| JP2016511253A (ja) | 植物成長調節化合物 | |
| CN111848592B (zh) | 4-氨基呋喃-2(5h)酮类化合物、其制备方法及应用 | |
| CN112442026B (zh) | 介离子衍生物及其制备方法和应用 | |
| CN110452167B (zh) | 喹啉类衍生物及其制备方法和用途 | |
| CN112574194B (zh) | 嘧啶嗡盐类化合物合成及应用 | |
| CN115872904B (zh) | 一种n-羟基-n苯基芳酰胺衍生物及其应用 | |
| CN112851665B (zh) | 新型介离子化合物及其在农业中的应用 | |
| CN113968854B (zh) | 新型鎓盐类化合物及其合成与应用 | |
| CN114249714B (zh) | 吡唑胺类化合物及其制备方法和应用 | |
| CN111925364B (zh) | 4-胺基呋喃-2(5h)酮衍生物及其制备方法和应用 | |
| CN112079800B (zh) | 被取代的烯胺羰基化合物及其制备方法和应用 | |
| CN114369090A (zh) | 一种介离子化合物及其制备方法和应用 | |
| CN112794817A (zh) | 喹啉衍生物及其制备方法和应用 | |
| CN113563327A (zh) | 新型介离子化合物及其合成与应用 | |
| CN114075177A (zh) | 4-胺基呋喃-2(5h)-酮衍生物及其制备方法和应用 | |
| CN113880805A (zh) | 4-取代的喹啉衍生物及其制备方法和应用 | |
| CN114621202A (zh) | 吡啶胺类化合物及其制备方法和应用 | |
| CN111620867A (zh) | 介离子杀虫剂 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |