CS255867B2 - Insecticide and process for preparing active component - Google Patents
Insecticide and process for preparing active component Download PDFInfo
- Publication number
- CS255867B2 CS255867B2 CS86754A CS75486A CS255867B2 CS 255867 B2 CS255867 B2 CS 255867B2 CS 86754 A CS86754 A CS 86754A CS 75486 A CS75486 A CS 75486A CS 255867 B2 CS255867 B2 CS 255867B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- methyl
- atom
- active ingredient
- Prior art date
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- 239000002917 insecticide Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 299
- 239000000203 mixture Substances 0.000 claims description 121
- -1 dimethylaminocarbonyl group Chemical group 0.000 claims description 111
- 238000000034 method Methods 0.000 claims description 81
- 239000004480 active ingredient Substances 0.000 claims description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 229910052801 chlorine Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 30
- 239000007858 starting material Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000011593 sulfur Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 239000012442 inert solvent Substances 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 11
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 3
- HRQVLVJUKAKOGR-UHFFFAOYSA-N 1-[(1-methylpyrazol-4-yl)methyl]-2-(nitromethylidene)-1,3-diazinane Chemical compound C1=NN(C)C=C1CN1C(=C[N+]([O-])=O)NCCC1 HRQVLVJUKAKOGR-UHFFFAOYSA-N 0.000 claims description 3
- JWWAMJAUUHKXGH-UHFFFAOYSA-N 2-(nitromethylidene)-3-(pyridin-3-ylmethyl)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=CN=C1 JWWAMJAUUHKXGH-UHFFFAOYSA-N 0.000 claims description 3
- LCZDSKLZYSOWMK-UHFFFAOYSA-N 2-methyl-5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,3-thiazole Chemical compound S1C(C)=NC=C1CN1C(=C[N+]([O-])=O)NCCC1 LCZDSKLZYSOWMK-UHFFFAOYSA-N 0.000 claims description 3
- LKNMJRFZEFJCKB-UHFFFAOYSA-N 2-methyl-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrazine Chemical compound C1=NC(C)=CN=C1CN1C(=C[N+]([O-])=O)NCC1 LKNMJRFZEFJCKB-UHFFFAOYSA-N 0.000 claims description 3
- JMZFPPKMYNTICK-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=C(Cl)N=C1 JMZFPPKMYNTICK-UHFFFAOYSA-N 0.000 claims description 3
- DITLWLXENULZBZ-UHFFFAOYSA-N 3-methyl-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-1,2-oxazole Chemical compound O1N=C(C)C=C1CN1C(=C[N+]([O-])=O)NCC1 DITLWLXENULZBZ-UHFFFAOYSA-N 0.000 claims description 3
- XZODFQRTNMIPJZ-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCCN1CC1=CC=C(Cl)N=C1 XZODFQRTNMIPJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- LHAUOPZSWKIXSW-UHFFFAOYSA-N 1-methyl-4-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrazole Chemical compound C1=NN(C)C=C1CN1C(=C[N+]([O-])=O)NCC1 LHAUOPZSWKIXSW-UHFFFAOYSA-N 0.000 claims description 2
- YPKTYPROJQOUBR-UHFFFAOYSA-N 2-(nitromethylidene)-3-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1SCCN1CC1=CC=C(C(F)(F)F)N=C1 YPKTYPROJQOUBR-UHFFFAOYSA-N 0.000 claims description 2
- GROQTGWKUWLQBQ-UHFFFAOYSA-N 2-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrazine Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=CC=N1 GROQTGWKUWLQBQ-UHFFFAOYSA-N 0.000 claims description 2
- XKVCBURYVNLQRB-FNORWQNLSA-N 2-chloro-5-[[(2e)-2-(nitromethylidene)imidazolidin-1-yl]methyl]-1,3-thiazole Chemical compound [O-][N+](=O)\C=C1/NCCN1CC1=CN=C(Cl)S1 XKVCBURYVNLQRB-FNORWQNLSA-N 0.000 claims description 2
- GUENHXVYSLGOHB-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]pyrimidine Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CN=C(Cl)N=C1 GUENHXVYSLGOHB-UHFFFAOYSA-N 0.000 claims description 2
- DKWNFDWLCUSKNX-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)-3-(pyridin-3-ylmethyl)imidazolidin-1-yl]methyl]pyridine Chemical compound C1CN(CC=2C=NC(Cl)=CC=2)C(=C[N+](=O)[O-])N1CC1=CC=CN=C1 DKWNFDWLCUSKNX-UHFFFAOYSA-N 0.000 claims description 2
- OLNLSIYRYORJQX-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrimidine Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=C(Cl)N=C1 OLNLSIYRYORJQX-UHFFFAOYSA-N 0.000 claims description 2
- ULPODHWNXKGNNU-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)pyrrolidin-1-yl]methyl]pyridine Chemical compound [O-][N+](=O)C=C1CCCN1CC1=CC=C(Cl)N=C1 ULPODHWNXKGNNU-UHFFFAOYSA-N 0.000 claims description 2
- PMJVPSDDURPMHB-UHFFFAOYSA-N 2-methyl-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-1,3-thiazole Chemical compound S1C(C)=NC=C1CN1C(=C[N+]([O-])=O)NCC1 PMJVPSDDURPMHB-UHFFFAOYSA-N 0.000 claims description 2
- JTKBDJBKFVXVQB-UHFFFAOYSA-N 2-methyl-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrimidine Chemical compound C1=NC(C)=NC=C1CN1C(=C[N+]([O-])=O)NCC1 JTKBDJBKFVXVQB-UHFFFAOYSA-N 0.000 claims description 2
- SNAYJEGWUMEKAV-UHFFFAOYSA-N 3-[(6-bromopyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=C(Br)N=C1 SNAYJEGWUMEKAV-UHFFFAOYSA-N 0.000 claims description 2
- MSLKSJDNNXJIEL-UHFFFAOYSA-N 3-[(6-bromopyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1SCCN1CC1=CC=C(Br)N=C1 MSLKSJDNNXJIEL-UHFFFAOYSA-N 0.000 claims description 2
- PSSQOQHTEFTBCY-UHFFFAOYSA-N 3-[(6-ethylpyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound C1=NC(CC)=CC=C1CN1C(=C[N+]([O-])=O)SCC1 PSSQOQHTEFTBCY-UHFFFAOYSA-N 0.000 claims description 2
- QHAUAXJMSGBAOI-UHFFFAOYSA-N 3-[(6-fluoropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=C(F)N=C1 QHAUAXJMSGBAOI-UHFFFAOYSA-N 0.000 claims description 2
- FVFSTVFUGPUFSR-UHFFFAOYSA-N 3-[(6-fluoropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1SCCN1CC1=CC=C(F)N=C1 FVFSTVFUGPUFSR-UHFFFAOYSA-N 0.000 claims description 2
- NXWDSILJBNBSDI-UHFFFAOYSA-N 3-[(6-methylpyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazinane Chemical compound C1=NC(C)=CC=C1CN1C(=C[N+]([O-])=O)SCCC1 NXWDSILJBNBSDI-UHFFFAOYSA-N 0.000 claims description 2
- OOHLVHUZMFQDQQ-UHFFFAOYSA-N 3-[(6-methylpyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound C1=NC(C)=CC=C1CN1C(=C[N+]([O-])=O)SCC1 OOHLVHUZMFQDQQ-UHFFFAOYSA-N 0.000 claims description 2
- WWPITHYQYHNEEJ-UHFFFAOYSA-N 3-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,2,5-thiadiazole Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=NSN=C1 WWPITHYQYHNEEJ-UHFFFAOYSA-N 0.000 claims description 2
- YKZCRCBRWNXUNJ-UHFFFAOYSA-N 5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,3-thiazole Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CN=CS1 YKZCRCBRWNXUNJ-UHFFFAOYSA-N 0.000 claims description 2
- FAWFDVWSMIKGEE-UHFFFAOYSA-N 5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-3-(trifluoromethyl)-1,2-oxazole Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CC(C(F)(F)F)=NO1 FAWFDVWSMIKGEE-UHFFFAOYSA-N 0.000 claims description 2
- IYMCSNKTQNGZAK-UHFFFAOYSA-N 5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]thiadiazole Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CN=NS1 IYMCSNKTQNGZAK-UHFFFAOYSA-N 0.000 claims description 2
- AFCKSKZYJPAKBU-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-1h-pyrazole Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CC=NN1 AFCKSKZYJPAKBU-UHFFFAOYSA-N 0.000 claims description 2
- ZGAUPFNHLNYGSP-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-2-(trifluoromethyl)-1,3-thiazole Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=C(C(F)(F)F)S1 ZGAUPFNHLNYGSP-UHFFFAOYSA-N 0.000 claims description 2
- YTHVNYGUJCKVIQ-UHFFFAOYSA-N 5-[[2-[bromo(nitro)methylidene]imidazolidin-1-yl]methyl]-2-chloropyridine Chemical compound [O-][N+](=O)C(Br)=C1NCCN1CC1=CC=C(Cl)N=C1 YTHVNYGUJCKVIQ-UHFFFAOYSA-N 0.000 claims description 2
- JXXIWLKFNFQTIT-UHFFFAOYSA-N CCCC(=O)C([N+]([O-])=O)=C1NCCN1CC1=CC=C(Cl)N=C1 Chemical compound CCCC(=O)C([N+]([O-])=O)=C1NCCN1CC1=CC=C(Cl)N=C1 JXXIWLKFNFQTIT-UHFFFAOYSA-N 0.000 claims description 2
- ZMVSOXBOHGLVSJ-UHFFFAOYSA-N n-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCCN1CC1=CN=C(Cl)S1 ZMVSOXBOHGLVSJ-UHFFFAOYSA-N 0.000 claims description 2
- ZBUHNISRCFLMLR-UHFFFAOYSA-N n-[1-[(2-chloropyrimidin-5-yl)methyl]-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=CN=C(Cl)N=C1 ZBUHNISRCFLMLR-UHFFFAOYSA-N 0.000 claims description 2
- DXFFSYLVVIMORD-UHFFFAOYSA-N n-[1-acetyl-3-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-ylidene]nitramide Chemical group [O-][N+](=O)N=C1N(C(=O)C)CCN1CC1=CC=C(Cl)N=C1 DXFFSYLVVIMORD-UHFFFAOYSA-N 0.000 claims description 2
- HJGRRIFNOOYFTC-UHFFFAOYSA-N n-[3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1SCCN1CC1=CC=C(Cl)N=C1 HJGRRIFNOOYFTC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
- FTAMBTJBGQBTOO-UHFFFAOYSA-N 3-methyl-5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,2-oxazole Chemical compound O1N=C(C)C=C1CN1C(=C[N+]([O-])=O)NCCC1 FTAMBTJBGQBTOO-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- YPIYSOFZUVFMSN-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrimidine Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=CN=C1 YPIYSOFZUVFMSN-UHFFFAOYSA-N 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 description 207
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 153
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
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- 239000011541 reaction mixture Substances 0.000 description 49
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000013078 crystal Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- 238000010992 reflux Methods 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 17
- 239000005977 Ethylene Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 241000607479 Yersinia pestis Species 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 10
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 9
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
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- FREJAOSUHFGDBW-UHFFFAOYSA-N pyrimidine-5-carbaldehyde Chemical compound O=CC1=CN=CN=C1 FREJAOSUHFGDBW-UHFFFAOYSA-N 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 9
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- HWIPUEAQJPNDPK-UHFFFAOYSA-N n-(1-methyl-4,5-dihydroimidazol-2-yl)nitramide Chemical compound CN1CCNC1=N[N+]([O-])=O HWIPUEAQJPNDPK-UHFFFAOYSA-N 0.000 description 1
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- VTRQFSMNIXPAKF-UHFFFAOYSA-N n-(4-methyl-3,4-dihydro-2h-pyrrol-5-yl)nitramide Chemical compound CC1CCNC1=N[N+]([O-])=O VTRQFSMNIXPAKF-UHFFFAOYSA-N 0.000 description 1
- IUVFTCWSRIIPLI-UHFFFAOYSA-N n-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)nitramide Chemical compound CC1COC(=N[N+]([O-])=O)N1 IUVFTCWSRIIPLI-UHFFFAOYSA-N 0.000 description 1
- WYFSUDYLUUQGHW-UHFFFAOYSA-N n-(5,5-dimethyl-1,4-dihydroimidazol-2-yl)nitramide Chemical compound CC1(C)CNC(=N[N+]([O-])=O)N1 WYFSUDYLUUQGHW-UHFFFAOYSA-N 0.000 description 1
- IEINRYFKCJSULM-UHFFFAOYSA-N n-(5,6-dihydro-4h-1,3-oxazin-2-yl)nitramide Chemical compound [O-][N+](=O)N=C1NCCCO1 IEINRYFKCJSULM-UHFFFAOYSA-N 0.000 description 1
- MOBSQMIOAGXXHU-UHFFFAOYSA-N n-(5,6-dihydro-4h-1,3-thiazin-2-yl)nitramide Chemical compound [O-][N+](=O)N=C1NCCCS1 MOBSQMIOAGXXHU-UHFFFAOYSA-N 0.000 description 1
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- BIUUVEPIRLLDGM-UHFFFAOYSA-N n-[(6-fluoropyridin-3-yl)methyl]-n'-propan-2-ylethane-1,2-diamine Chemical compound CC(C)NCCNCC1=CC=C(F)N=C1 BIUUVEPIRLLDGM-UHFFFAOYSA-N 0.000 description 1
- XZMSZNXOXBJPQQ-UHFFFAOYSA-N n-[1-(1,2,5-thiadiazol-3-ylmethyl)-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=NSN=C1 XZMSZNXOXBJPQQ-UHFFFAOYSA-N 0.000 description 1
- AEKWWEYCSQBVMJ-UHFFFAOYSA-N n-[1-(pyridin-3-ylmethyl)-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=CC=CN=C1 AEKWWEYCSQBVMJ-UHFFFAOYSA-N 0.000 description 1
- OWRSHPAYDYCHSJ-UHFFFAOYSA-N n-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)NC1=NCCN1CC1=CN=C(Cl)S1 OWRSHPAYDYCHSJ-UHFFFAOYSA-N 0.000 description 1
- CDSIGHUKOXXMJF-UHFFFAOYSA-N n-[1-[(6-bromopyridin-3-yl)methyl]-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=CC=C(Br)N=C1 CDSIGHUKOXXMJF-UHFFFAOYSA-N 0.000 description 1
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- XICBOBNYBAUHNC-UHFFFAOYSA-N n-[1-[[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=CC=C(OCC(F)(F)F)N=C1 XICBOBNYBAUHNC-UHFFFAOYSA-N 0.000 description 1
- BVQVUPOSSMLHHN-UHFFFAOYSA-N n-[1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=CC=C(C(F)(F)F)N=C1 BVQVUPOSSMLHHN-UHFFFAOYSA-N 0.000 description 1
- IIBVHOKCAGDUBE-UHFFFAOYSA-N n-[1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCCN1CC1=CC=C(C(F)(F)F)N=C1 IIBVHOKCAGDUBE-UHFFFAOYSA-N 0.000 description 1
- UKFGIPIPAFSXSD-UHFFFAOYSA-N n-[3-(pyridin-4-ylmethyl)-1,3-thiazolidin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1SCCN1CC1=CC=NC=C1 UKFGIPIPAFSXSD-UHFFFAOYSA-N 0.000 description 1
- FCKWDQUVHDZOJU-UHFFFAOYSA-N n-benzyl-n'-[(6-chloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound C1=NC(Cl)=CC=C1CNCCNCC1=CC=CC=C1 FCKWDQUVHDZOJU-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- LZTIMERBDGGAJD-UHFFFAOYSA-N nithiazine Chemical compound [O-][N+](=O)C=C1NCCCS1 LZTIMERBDGGAJD-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical class [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- LVYHTHBJVCOSPP-UHFFFAOYSA-N phenyl 2-nitramido-4,5-dihydroimidazole-1-carboxylate Chemical compound [O-][N+](=O)N=C1NCCN1C(=O)OC1=CC=CC=C1 LVYHTHBJVCOSPP-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JJIHENIPUIXQDM-UHFFFAOYSA-N thiadiazole-5-carbaldehyde Chemical compound O=CC1=CN=NS1 JJIHENIPUIXQDM-UHFFFAOYSA-N 0.000 description 1
- AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical class C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Control Of Throttle Valves Provided In The Intake System Or In The Exhaust System (AREA)
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Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60018628A JPH0649699B2 (ja) | 1985-02-04 | 1985-02-04 | ニトロメチレン誘導体、その製法及び殺虫剤 |
JP60018627A JPH066585B2 (ja) | 1985-02-04 | 1985-02-04 | ニトロメチレン誘導体、その製法及び殺虫剤 |
JP60023683A JPH07613B2 (ja) | 1985-02-12 | 1985-02-12 | ニトロメチレン誘導体、その製法及び殺虫剤 |
JP60106854A JPS61267575A (ja) | 1985-05-21 | 1985-05-21 | ニトロイミノ誘導体、その製法及び殺虫剤 |
JP10685385A JPH0629258B2 (ja) | 1985-05-21 | 1985-05-21 | 殺虫性ニトロメチレン誘導体 |
JP60219082A JPH0730070B2 (ja) | 1985-10-03 | 1985-10-03 | 新規複素環式化合物 |
Publications (2)
Publication Number | Publication Date |
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CS75486A2 CS75486A2 (en) | 1987-07-16 |
CS255867B2 true CS255867B2 (en) | 1988-03-15 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CS86754A CS255867B2 (en) | 1985-02-04 | 1986-02-03 | Insecticide and process for preparing active component |
Country Status (19)
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US (9) | US4742060A (fr) |
EP (1) | EP0192060B1 (fr) |
KR (1) | KR930006348B1 (fr) |
AT (1) | ATE67493T1 (fr) |
AU (1) | AU584388B2 (fr) |
BR (1) | BR8600428A (fr) |
CA (1) | CA1276018C (fr) |
CS (1) | CS255867B2 (fr) |
DE (1) | DE3681465D1 (fr) |
DK (2) | DK172805B1 (fr) |
GR (1) | GR860308B (fr) |
HK (1) | HK34294A (fr) |
HU (2) | HU202365B (fr) |
IL (1) | IL77750A (fr) |
NL (1) | NL971014I2 (fr) |
NZ (1) | NZ215008A (fr) |
PH (1) | PH30435A (fr) |
PL (1) | PL149199B1 (fr) |
SG (1) | SG138493G (fr) |
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-
1995
- 1995-03-15 US US08/404,849 patent/US5580889A/en not_active Expired - Lifetime
-
1996
- 1996-06-12 US US08/662,096 patent/US5750704A/en not_active Expired - Fee Related
-
1997
- 1997-07-17 NL NL971014C patent/NL971014I2/nl unknown
-
1998
- 1998-01-23 US US09/012,620 patent/US6022967A/en not_active Expired - Fee Related
-
1999
- 1999-05-11 US US09/309,988 patent/US6297374B1/en not_active Expired - Fee Related
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
IF00 | In force as of 2000-06-30 in czech republic | ||
MK4A | Patent expired |
Effective date: 20010203 |