JPH0582391B2 - - Google Patents
Info
- Publication number
- JPH0582391B2 JPH0582391B2 JP13294384A JP13294384A JPH0582391B2 JP H0582391 B2 JPH0582391 B2 JP H0582391B2 JP 13294384 A JP13294384 A JP 13294384A JP 13294384 A JP13294384 A JP 13294384A JP H0582391 B2 JPH0582391 B2 JP H0582391B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- nitromethylene
- general formula
- represented
- alkyl group
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000004519 manufacturing process Methods 0.000 claims description 24
- -1 nitromethylene Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002917 insecticide Substances 0.000 claims description 6
- OHXNZFJZRFHBLX-UHFFFAOYSA-N 2-(nitromethylidene)imidazolidine Chemical compound [O-][N+](=O)C=C1NCCN1 OHXNZFJZRFHBLX-UHFFFAOYSA-N 0.000 claims description 4
- GOBRRFQNYBGHAU-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-diazinane Chemical compound [O-][N+](=O)C=C1NCCCN1 GOBRRFQNYBGHAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 4
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 1
- AWZKZPGAZRQOQO-UHFFFAOYSA-N 1-[(6-methylpyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-diazinane Chemical compound C1=NC(C)=CC=C1CN1C(=C[N+]([O-])=O)NCCC1 AWZKZPGAZRQOQO-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 11
- 241000607479 Yersinia pestis Species 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241000490513 Ctenocephalides canis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XMZJJLHHTJLEMK-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-dithiolane Chemical compound [O-][N+](=O)C=C1SCCS1 XMZJJLHHTJLEMK-UHFFFAOYSA-N 0.000 description 1
- DQHLXESBWCWKIY-UHFFFAOYSA-N 2-(nitromethylidene)-3,4-dihydro-1h-pyrimidine Chemical compound [O-][N+](=O)C=C1NCC=CN1 DQHLXESBWCWKIY-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- 241000175828 Adoxophyes orana Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000600972 Agriotes fuscicollis Species 0.000 description 1
- 241000519878 Anomala rufocuprea Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000726760 Cadra cautella Species 0.000 description 1
- 241001313742 Callosobruchus chinensis Species 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241001509962 Coptotermes formosanus Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001481760 Erethizon dorsatum Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 241000785585 Gryllotalpa africana Species 0.000 description 1
- 241001299252 Henosepilachna vigintioctomaculata Species 0.000 description 1
- 241000258915 Leptinotarsa Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241001177134 Lyctus Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241001442207 Monochamus alternatus Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000721623 Myzus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000596535 Pseudococcus comstocki Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000722251 Rhodnius Species 0.000 description 1
- 241000125162 Rhopalosiphum Species 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- 241000254154 Sitophilus zeamais Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241000283614 Stephanitis nashi Species 0.000 description 1
- 241001494139 Stomoxys Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241001259047 Trichodectes Species 0.000 description 1
- 241001630065 Unaspis yanonensis Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical group BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000003860 storage Methods 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59132943A JPS6112682A (ja) | 1984-06-29 | 1984-06-29 | 殺虫性ニトロメチレン誘導体 |
| ZW50/85A ZW5085A1 (en) | 1984-04-13 | 1985-03-21 | Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides |
| PH32074A PH22486A (en) | 1984-04-13 | 1985-03-29 | Nitromethylene derivatives, intermediante thereof, process for production thereof |
| PT80231A PT80231B (pt) | 1984-04-13 | 1985-04-03 | Processo para a preparacao de derivados de nitrometileno com efeito insecticida |
| US06/720,838 US4678795A (en) | 1984-04-13 | 1985-04-08 | 1-pyridylmethyl-2-nitromethylene-1,3-diazacycloalkane insecticides |
| DE8585104254T DE3571131D1 (en) | 1984-04-13 | 1985-04-09 | Nitromethylene derivatives, intermediates, and process for their preparation as insecticides |
| EP85104254A EP0163855B1 (de) | 1984-04-13 | 1985-04-09 | Nitromethylen-Derivate, Zwischenprodukte für diese, Verfahren zu ihrer Herstellung sowie Insektizide |
| AT85104254T ATE44145T1 (de) | 1984-04-13 | 1985-04-09 | Nitromethylen-derivate, zwischenprodukte fuer diese, verfahren zu ihrer herstellung sowie insektizide. |
| IL74864A IL74864A (en) | 1984-04-13 | 1985-04-10 | 1-pyridylalkyl-2-nitromethylene-1,3,-diaza cycloalkanes,their production and insecticidal compositions containing them |
| NZ211738A NZ211738A (en) | 1984-04-13 | 1985-04-10 | Heterocyclic nitromethylene derivatives and insecticidal compositions |
| TR22165A TR22165A (tr) | 1984-04-13 | 1985-04-11 | Nitrometilen tuerevleri,bunlar icin ara ueruenler bunlarin ueretimi icin usueller ve ensektisidler |
| CA000478814A CA1262725A (en) | 1984-04-13 | 1985-04-11 | Nitromethylene derivatives, intermediates thereof, processes for production thereof, and insecticides |
| OA58567A OA07991A (fr) | 1984-04-13 | 1985-04-12 | Dérivés de nitrométhylène, produits intermédiaires correspondants, leur procédé de production et insecticides contenant ces dérivés. |
| KR1019850002454A KR910004433B1 (ko) | 1984-04-13 | 1985-04-12 | 니트로메틸렌 유도체의 제조방법 |
| AR85300060A AR241909A1 (es) | 1984-04-13 | 1985-04-12 | 1-n-piridilalquil-2-(nitrometilen)-imidazolidinas y tetrahidropirimidinas substituidas, procedimiento para su preparacion, intermediarios, composiciones insecticidas que los contienen. |
| ES542202A ES542202A0 (es) | 1984-04-13 | 1985-04-12 | Procedimiento para la obtencion de un derivado de nitrometi-leno |
| HU851372A HU196029B (en) | 1984-04-13 | 1985-04-12 | Insecticides comprising nitro-methylene derivatives as active ingredient and process for producing nitro-methylene derivatives |
| BR8501739A BR8501739A (pt) | 1984-04-13 | 1985-04-12 | Processo para a preparacao de um derivado de nitrometileno,composicao inseticida,processo para a preparacao de um composto,processos para o combate de insetos e para a preparacao de composicoes |
| AU41097/85A AU571961B2 (en) | 1984-04-13 | 1985-04-12 | Pyridine derivatives |
| DK167885A DK169072B1 (da) | 1984-04-13 | 1985-04-12 | 1-Pyridylalkylsubstitueret imidazolidinyl-2- eller hexahydropyrimidinyl-2-nitromethylenderivat og salte deraf, fremgangsmåde til dets fremstilling, insekticider indeholdende det samt dets anvendelse til insektbekæmpelse, og fremgangsmåde til fremstilling af insekticider indeholdende det |
| GR851583A GR851583B (en, 2012) | 1984-06-29 | 1985-06-27 | |
| US07/029,303 US4774247A (en) | 1984-04-13 | 1987-03-23 | Nitromethylene derivative insecticides |
| US07/130,697 US4812571A (en) | 1984-04-13 | 1987-12-09 | N-(substituted pyridyl-alkyl) alkylenediamine intermediates for insecticides |
| AU10183/88A AU597772B2 (en) | 1984-04-13 | 1988-01-11 | Novel pyridine derivatives and processes for their production |
| DK198891A DK171643B1 (da) | 1984-04-13 | 1991-12-10 | Pyridylalkylsubstituerede ethylen- og propylendiaminer og fremgangsmåde til deres fremstilling |
| JP5166278A JP2539159B2 (ja) | 1984-06-29 | 1993-06-11 | 殺虫性ニトロメチレン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59132943A JPS6112682A (ja) | 1984-06-29 | 1984-06-29 | 殺虫性ニトロメチレン誘導体 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18286391A Division JPH0517447A (ja) | 1991-06-29 | 1991-06-29 | 新規ジアミン類 |
| JP5166278A Division JP2539159B2 (ja) | 1984-06-29 | 1993-06-11 | 殺虫性ニトロメチレン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6112682A JPS6112682A (ja) | 1986-01-21 |
| JPH0582391B2 true JPH0582391B2 (en, 2012) | 1993-11-18 |
Family
ID=15093121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59132943A Granted JPS6112682A (ja) | 1984-04-13 | 1984-06-29 | 殺虫性ニトロメチレン誘導体 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6112682A (en, 2012) |
| GR (1) | GR851583B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2539159B2 (ja) * | 1984-06-29 | 1996-10-02 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロメチレン誘導体 |
| WO1991018882A1 (en) * | 1990-05-29 | 1991-12-12 | Nippon Soda Co., Ltd. | N-substituted heterocyclic amidine derivative |
| JP3071340B2 (ja) * | 1993-06-02 | 2000-07-31 | セントラル硝子株式会社 | ２−クロロ−ピリジンメタノールの製造方法 |
-
1984
- 1984-06-29 JP JP59132943A patent/JPS6112682A/ja active Granted
-
1985
- 1985-06-27 GR GR851583A patent/GR851583B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6112682A (ja) | 1986-01-21 |
| GR851583B (en, 2012) | 1985-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |