KR960041158A - 살충제로서 벤조페논 히드라존 유도체 - Google Patents
살충제로서 벤조페논 히드라존 유도체 Download PDFInfo
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- KR960041158A KR960041158A KR1019960015136A KR19960015136A KR960041158A KR 960041158 A KR960041158 A KR 960041158A KR 1019960015136 A KR1019960015136 A KR 1019960015136A KR 19960015136 A KR19960015136 A KR 19960015136A KR 960041158 A KR960041158 A KR 960041158A
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- South Korea
- Prior art keywords
- hydrogen
- optionally substituted
- alkyl
- substituted
- halogen
- Prior art date
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- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical class C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 title abstract 3
- 239000002917 insecticide Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 38
- 239000001257 hydrogen Substances 0.000 claims abstract 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract 30
- 150000002431 hydrogen Chemical class 0.000 claims abstract 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract 22
- 150000002367 halogens Chemical class 0.000 claims abstract 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 4
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims abstract 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 23
- -1 cyano, methoxy, ethoxy Chemical group 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 239000012442 inert solvent Substances 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004673 propylcarbonyl group Chemical group 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- 235000011331 Brassica Nutrition 0.000 claims 1
- 241000219198 Brassica Species 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 241000927721 Tritia Species 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 238000005067 remediation Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/76—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/08—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/48—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/16—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/04—Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
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Abstract
본 발명은 신규한 하기 알반식 (Ⅰ)의 벤조페논히드라존 유도체에 관한 것이다.
상기 식에서, R1은 할로겐이고, R2는 수소 또는 C1-4알킬이며, R3는 시아노, 임의로 치환된 C1-4알킬, C2-4알케닐 또는 C3-4알키닐, C1-4알킬카보닐, 또는 C1-4 알콕시티오카보닐이고, R4는 수소, 페닐, 벤질, 임의로 치환된 C1-8알킬, 임의로 치환 된 C2-8알케닐, -CO-R8, -CO-O-R9또는이며, R5는 수소, 포르밀, 페닐, 임의로 치환된 C1-8알킬, 임의로 치환된 C2-8알케닐, 임의로 치환된 C3-8알키닐, 임의로 치환된 C1-8알킬카보닐, 임의로 치환된 C1-6알킬옥살릴, 임의로 치환된 C1-8알콕시카보닐, 임의로 치환된 C1-8알콕시옥살릴, 임의로 치환된 C3-8사이클로알킬카보닐, 임의로 치환된 C2-8알케닐카보닐 또는 임의로 치환된 벤조일이고, R6는 수소 또는 할로겐이며, R7은 수소, 할로겐 또는 C1-2알킬이고, n은 0,1 또는 2이며, 단 n이 0인 경우에 R3는 시아노, C1-4알킬카보닐 또는 C1-4알콕시티오카보닐이며, 는 안티 형태 또는 신형태의 단일 결합이다. 일반식(Ⅰ)의 벤조페논히드라존 유도체는 뛰어난 살충 활성을 갖는다.
Description
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Claims (9)
- 일반식 (Ⅰ)의 화합물.상기 식에서, R1은 할로겐이고, R2는 수소 또는 C1-4알킬이며, R3는 시아노, 임의로 치환된 C1-4알킬, C2-4알케닐 또는 C3-4알키닐, C1-4알킬카보닐, 또는 C1-4 알콕시티오카보닐이고, R4는 수소, 페닐, 벤질, 임의로 치환된 C1-8알킬, 임의로 치환된 C2-8알케닐, -CO-R8, -CO-O-R9또는이며, R5는 수소, 포르밀, 페닐, 임의로 치환된 C1-8알킬, 임의로 치환된 C2-8알케닐, 임의로 치환된 C3-8알키닐, 임의로 치환된 C1-8알킬카보닐, 임의로 치환된 C1-6알킬옥살릴, 임의로 치환된 C1-8알콕시카보닐, 임의로 치환된 C1-8알콕시옥살릴, 임의로 치환된 C3-8사이클로알킬카보닐, 임의 치환된 C2-8알케닐카보닐 또는 임의로 치환된 벤조일이고, R6는 수소 또는 할로겐이며, R7은 수소, 할로겐 또는 C1-2알킬이고, n은 0,1 또는 2이며, 단 n이 0인 경우에 R3는 시아노, C1-4알킬카보닐 또는 C1-4알콕시티오카보닐이며, 는 안티(Anti) 형태 또는 신(Syn) 형태의 단일 결합이고, R8은 임의로 치환된 C1-8알킬, 임의로 치환된 C2-8알케닐, 임의로 치환된 페닐, 임의로 치환된 C3-8사이클로알킬, 임의로 치환된 C1-8알킬카보닐 또는 임의로 치환된 C1-8알콕시카보닐 또는 수소이며, R9는 임의로 치환된 C1-8알킬, 임의로 치환된 C3-8사이클로알킬, 임의로 치환된 C2-8알케닐 또는 임의로 치환된 C3-8알키닐이고, R10은 수소 또는 C1-4알킬이며, R11은 수소, 임의로 치환된 C1-4알킬 또는 임의로 치환된 페닐이고, Z는 산소 또는 황이다.
- 제1항에 있어서, (a) 일반식 (Ⅱ)의 화합물을 불활성 용매의 존재하, 및 경우에 따라 산 촉매의 존재하에서 일반식 (Ⅲ)의 화합물과 반응시켜 R5가 수소인 일반식 (Ⅰ)의 화합물을 제조하거나, (b) 일반식 (Ⅳ)의 화합물을 불활성 용매의 존재하에서 일반식 (Ⅴ)의 화합물과 반응시켜 R5가 수소이고, R4는이며, R11이 수소가 아닌 경우에 R11은 R12에 의해 대체되고, 이때 R12는 임의로 치환된 C1-4알킬 또는 임의로 치환된 페닐인 일반식 (Ⅰ)의 화합물을 제조하거나, (c) 일반식 (Ⅳ)의 화합물을 불활성 용매의 존재하, 및 경우에 따라 산 결합제의 존재하에 일반식 (Ⅵ)의 화합물과 반응시켜 R4가 -CO-R8또는 -CO-O-R9이고, 단 R8이 수소가 아닌 경우에 R8또는 -O-R9는 R13에 의해 대체되는 일반식(Ⅰ)의 화합물을 제조하거나, (d) 일반식 (Ⅶ)의 화합물을 불활성 용매의 존재하, 및 경우에 따라 산 결합제의 존재하에서 일발식 (Ⅷ)의 화합물과 반응시켜 R5가 수소가 아닌 경우에 R5는 R14에 의해 대체되는 일반식 (Ⅰ)의 화합물을 제조하거나, (e) 일반식 (Ⅸ)의 화합물을 불활성 용매의 존재하에 산화시켜 n이 1일 일반식 (Ⅰ)의 화합물을 제조하거나, (f) 일반식 (Ⅹ)의 화합물을 불활성 용매의 존재하에서 산화시켜 n이 2인 일반식 (Ⅰ)의 화합물을 특징으로하여, 제1항에 따르는 일반식 (Ⅰ)의 화합물을 제조하는 방법.상기 식에서, R1, R2, R3, R4, R5, R6, R7및 n은 제1항에서 정의한 바와 같고, R12는 임의로 치환된 C1-4알킬 또는 임의로 치환된 페닐이며, hal은 염소 또는 브롬이고, R13은 R8또는 -O-R9이며, R14는 R8또는 -O-R9이고, q는 0 또는 1이다.
- 제1항에 있어서, R1이 할로겐이고, R2는 수소 또는 C1-3알킬이며, R3는 시아노 또는 할로겐, 시아노, 메톡시, 에톡시 및 트리메틸실릴로 구성된 그룹중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 C1-4알킬이거나, C2-3알케닐, 프로파길, 메틸카보닐, 메톡시티오카보닐 또는 에톡시티오카보닐이고, R4는 수소, C1-4알킬, C2-4알케닐, 페닐, 벤질, -CO-R8, -CO-O-R9또는이며, R5는 수소, 포르밀, 페닐, 또는 할로겐, 시아노, C1-4알콕시, C1-4알킬티오, 하이드록시카보닐, C1-4알콕시카보닐, 페닐, 할로겐에 의해 치환된 페닐 및 메톡시페닐로 구성된 그룹중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 C1-6알킬이거나, C2-6알케닐, C3-6알키닐, C1-6알킬카보닐, C1-6할로겐알킬카보닐, C1-4알콕시-C1-6알킬카보닐, C1-6알킬옥살릴, 또는 C3-6사이클로알킬 및 C1-4알콕시로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 C1-6알콕시카보닐이거나, C1-6알콕시옥살릴, 또는 C1-4알킬에 의해 치환될 수 있는 C3-6사이클로알킬카보닐, 또는 페닐에 의해 치환될 수 있는 C2-6알케닐카보닐이거나, 할로겐, 니트로, 시아노, C14알콕시 및 C14알킬티오로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 벤조일이고, R6는 수소 또는 할로겐이며, R7은 수소, 할로겐 또는 C1-2알킬이고, n은 0,1 또는 2이며, 단 n이 0인 경우에 R3는 시아노, 메틸카보닐, 메톡시티오카보닐 또는 에톡시티오카보닐이며, 는 안티 형태 또는 신 형태의 단일 결합이고, R8은 할로겐, 시아노, C1-4알콕시, C1-4알콜시카보닐 및 페녹시로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 C1-6알킬이거나, 할로겐 및 페닐로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환 될 수 있는 C2-6알케닐이거나, 할로겐, 니트로, 시아노, C1-4알킬, C1-4알콕시 및 C1-4알킬티오로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 페닐이거나, C1-4알킬에 의해 치환될 수 있는 C3-6사이클로알킬이거나, C16알킬카보닐, C16알콕시카보닐 또는 수소이며, R9는 할로겐, 페닐, 4-니트로페닐, 트리메틸실릴 및 C3-6사이클로알킬로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 C1-6알킬이거나, C3-6사이클로알킬, 도는 페닐에 의해 치환될 수 있는 C2-6알케닐, 또는 C3-6알키닐이고, R10은 수소 또는 C1-4알킬이며, R11은 수소, 할로겐에 의해 치환될 수 있는 C1-4알킬, 또는 할로겐, C1-4알콕시 및 C1-4할로알콕시로 구성된 그룹 중에서 선택된 하나 이상의 치환체에 의해 치환될 수 있는 페닐이고, Z는 산소 또는 황인 일반식 (Ⅰ)의 화합물.
- 제1항에 있어서, R1이 불소, 염소, 브롬 또는 요오드이고, R2는 수소, 메틸, 에틸 또는 n-프로필이며, R3는 시아노, 메틸, 에틸, 프로필, 이소프로필, n-부틸, 2급-부틸, 시아노메틸, 플루오로메틸, 클로로메틸, 디플루오로메틸, 트리플루오로메틸, 2-플루오로에틸, 2-클로로에틸, 2,2-디플루오로에틸, 2,2,2-트리플루오로에틸, 3-플루오로프로필, 3-클로로프로필, 2,2,3,3-테트라플루오로프로필, 메톡시메틸, 에톡시메틸, 트리메틸실릴메틸, 비닐, 알릴, 프로파길, 메틸카보닐 또는 에톡시티오카보닐이고, R4는 수소, 메틸, 에틸, 프로필, 이소프로필, n-부틸, 3급-부틸, 알릴, 페닐, 벤질, -CO-R8, -CO-O-R9또는이며, R5는 수소, 메틸, 에틸, 프로필, 이소프로필, n-부틸, 3급-부틸, n-펜틸, n-헥실, 메톡시메틸, 에톡시메틸, 메틸티오메틸, 메틸티오에틸, 메톡시카보닐메틸, 에톡시카보닐메틸, 2-에톡시카보닐에틸, 디플루오로메틸, 2-클로로에틸, 2,2-디플루오로에틸, 2,2,2-트리플루오로에틸, 시아노메틸, 시아노에틸, 비닐, 알릴, 프로파길, 페닐, 벤조일, 신나모일, 벤질, 4-클로로벤조일, 4-메톡시벤조일, 포르밀, 메틸카보닐, 에틸카보닐, 프로필카보닐, 이소프로필카보닐, n-부틸카보닐, 2,2,2-트리플루오로에틸카보닐, 5-브로모펜틸카보닐, 메톡시메틸카보닐, 메틸옥살릴, 에틸옥살릴, 프로필옥살릴, 이소프로필옥살릴, n-부틸옥살릴, 메톡시카보닐, 에톡시카보닐, 프로폭시카보닐, 부톡시카보닐, 메톡시옥살릴, 에톡시옥살릴, 프로폭시옥살릴, 부톡시옥살릴, 사이클로프로필카보닐, 1-메틸사이클로프로필카보닐, 사이클로프로필메톡시카보닐, 2-메톡시에톡시카보닐 또는 하이드록시카보닐에틸이고, R6는 수소, 불소 또는 염소이며, R7은 수소, 브롬 또는 메틸이고, n은 0,1 또는 2이며, 단 n이 0인 경우에 R3는 메틸카보닐 또는 에톡시티오카보닐이며, 는 안티 형태 또는 신 형태의 단일 결합이고, R8은 메틸, 에틸, 프로필, 이소프로필, n-부틸, 이소부틸, 2급-부틸, 3급-부틸, n-펜틸, n-헥실, 시아노메틸, 2-클로로에틸, 3-클로로프로필, 4-클로로부틸, 메톡시메틸, 2-메톡시에틸, 페녹시메틸, 에톡시카보닐메틸, 비닐, 이소프로페닐, 1-프로페닐, 2,3,3-트리플루오로-2-프로페닐, 페닐, 4-클로로페닐, 4-브로모페닐, 4-메틸페닐, 4-메톡시페닐, 스티릴, 사이클로프로필, 사이클로펜틸, 사이클로헥실, 1-메틸사이클로프로필, 메틸카보닐, 에틸카보닐, 프로필카보닐, 메톡시카보닐, 에톡시카보닐, 프로폭시카보닐 또는 수소이고, R9는 메틸, 에질, 프로필, 이소프로필, n-부틸, 이소부틸, 3급-부틸, 2급-부틸, n-펜틸, 네오펜틸, 2-메틸부틸, n-헥실, 트리메틸실릴메틸, 알릴, 사이클로펜틸, 사이클로헥실, 2-메틸-2-프로페닐, 프로파길, 2-클로로에틸, 2,2,2-트리플루오로에틸, 2,2,3,3-테트라플루오로프로필, 사이클로프로필메틸, 사이클로헥실메틸, 벤질 또는 4-니트로벤질이고, R10은 수소 또는 메틸이며, R11은 수소, 메틸, 에틸, 2-클로로에틸, 페닐, 2-클로로페닐, 2-메톡시페닐 또는 4-트리플루오로메톡시페닐이고, Z는 산소 또는 황인 일반식(Ⅰ)의 화합물.
- 제1항에 따르는 일반식(Ⅰ)의 화합물을 적어도 하나 함유함을 특징으로 하는 농약.
- 해충을 구제하기 위한 제1항에 따르는 일반식 (Ⅰ)의 화합물의 용도.
- 제1항에 따르는 일반식 (Ⅰ)의 화합물을 해충 및/또는 그들의 환경에 작용시킴을 특징으로 하여 해충을 구제하는 방법.
- 제1항에 따르는 일반식 (Ⅰ)의 화합물을 중량제 및/또는 계면활성제와 혼합시킴을 특징으로 하여 농약을 제조하는 방법.
- 일반식 (ⅩⅩⅨ)의 화합물.상기 식에서, R1은 할로겐이고, R2는 수소 또는 C1-4알킬이며, R3는 수소 또는 할로겐이고, R7은 수소, 할로겐 또는 C1-2알킬이며, n은 0,1 또는 2이고, X는 시아노, 임의로 치환된 C1-4알킬, C2-4알케닐, C3-4알키닐, C1-4알킬카보닐, C1-4알콕시티오카보닐 또는 카복스아미딘 및 그의 염이며, 단 X가 시아노, C1-4알킬카보닐, C1-4알콕시티오카보닐 또는 카복스아미딘 및 그의 염인 경우에는 n은 0이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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-
1996
- 1996-05-03 AT AT96106956T patent/ATE187165T1/de not_active IP Right Cessation
- 1996-05-03 EP EP96106956A patent/EP0742202B1/en not_active Expired - Lifetime
- 1996-05-03 DE DE69605353T patent/DE69605353D1/de not_active Expired - Lifetime
- 1996-05-06 AU AU52086/96A patent/AU5208696A/en not_active Abandoned
- 1996-05-08 TR TR96/00373A patent/TR199600373A2/xx unknown
- 1996-05-08 KR KR1019960015136A patent/KR960041158A/ko not_active Application Discontinuation
- 1996-05-09 MX MX9601757A patent/MX9601757A/es not_active Application Discontinuation
- 1996-05-10 TW TW085105516A patent/TW323273B/zh active
- 1996-05-10 CO CO96023681A patent/CO4650113A1/es unknown
- 1996-05-10 US US08/644,139 patent/US6077866A/en not_active Expired - Fee Related
- 1996-05-10 AR ARP960102525A patent/AR002738A1/es unknown
- 1996-05-11 EG EG40496A patent/EG20800A/xx active
- 1996-05-11 CN CN96107424A patent/CN1143630A/zh active Pending
- 1996-05-13 JP JP8141187A patent/JPH09278744A/ja active Pending
- 1996-05-13 BR BR9602237A patent/BR9602237A/pt not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100416021B1 (ko) * | 1995-01-20 | 2004-06-09 | 와이어쓰 홀딩스 코포레이션 | 벤조페논을함유하는살균제조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09278744A (ja) | 1997-10-28 |
| CO4650113A1 (es) | 1998-09-03 |
| US6077866A (en) | 2000-06-20 |
| TW323273B (ko) | 1997-12-21 |
| BR9602237A (pt) | 1998-01-13 |
| EG20800A (en) | 2000-03-29 |
| DE69605353D1 (de) | 2000-01-05 |
| EP0742202B1 (en) | 1999-12-01 |
| AU5208696A (en) | 1996-11-21 |
| CN1143630A (zh) | 1997-02-26 |
| EP0742202A3 (en) | 1997-03-19 |
| MX9601757A (es) | 1997-07-31 |
| TR199600373A2 (tr) | 1996-12-21 |
| AR002738A1 (es) | 1998-04-29 |
| ATE187165T1 (de) | 1999-12-15 |
| EP0742202A2 (en) | 1996-11-13 |
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