DE2142653C3 - l,l-Bis-(subst-phenyl)-2-nitroalkane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Insektizide - Google Patents
l,l-Bis-(subst-phenyl)-2-nitroalkane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende InsektizideInfo
- Publication number
- DE2142653C3 DE2142653C3 DE2142653A DE2142653A DE2142653C3 DE 2142653 C3 DE2142653 C3 DE 2142653C3 DE 2142653 A DE2142653 A DE 2142653A DE 2142653 A DE2142653 A DE 2142653A DE 2142653 C3 DE2142653 C3 DE 2142653C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- bis
- compound
- nitropropane
- phenyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 title description 40
- 238000000034 method Methods 0.000 title description 13
- 239000002917 insecticide Substances 0.000 title description 12
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- -1 methoxy, ethoxy, methylthio Chemical group 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 5
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 4
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- AEHWKBXBXYNPCX-UHFFFAOYSA-N ethylsulfanylbenzene Chemical compound CCSC1=CC=CC=C1 AEHWKBXBXYNPCX-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- GJTGBELZYSGOBM-UHFFFAOYSA-N 1-ethoxy-4-[1-(4-ethoxyphenyl)-2-nitroethyl]benzene Chemical compound C1=CC(OCC)=CC=C1C(C[N+]([O-])=O)C1=CC=C(OCC)C=C1 GJTGBELZYSGOBM-UHFFFAOYSA-N 0.000 description 2
- CSMWRHUVDRHGAR-UHFFFAOYSA-N 1-methoxy-4-(2-nitropropyl)benzene Chemical compound COC1=CC=C(CC(C)[N+]([O-])=O)C=C1 CSMWRHUVDRHGAR-UHFFFAOYSA-N 0.000 description 2
- SUGZATOHBPXTDV-UHFFFAOYSA-N 2-nitrobutane Chemical compound CCC(C)[N+]([O-])=O SUGZATOHBPXTDV-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000006842 Henry reaction Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229940081310 piperonal Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- KQBSGQRDZLRNFT-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-nitropropan-1-ol Chemical compound [O-][N+](=O)C(C)C(O)C1=CC=C2OCOC2=C1 KQBSGQRDZLRNFT-UHFFFAOYSA-N 0.000 description 1
- OBOFDFZZWCVULJ-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-2-nitrobutan-1-ol Chemical compound CCOC1=CC=C(C=C1)C(O)C(CC)[N+]([O-])=O OBOFDFZZWCVULJ-UHFFFAOYSA-N 0.000 description 1
- GKVATCHXPWRHKY-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-2-nitropropan-1-ol Chemical compound CCOC1=CC=C(C(O)C(C)[N+]([O-])=O)C=C1 GKVATCHXPWRHKY-UHFFFAOYSA-N 0.000 description 1
- WMZYDOIBIPAOHJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-nitrobutan-1-ol Chemical compound CCC([N+]([O-])=O)C(O)C1=CC=C(OC)C=C1 WMZYDOIBIPAOHJ-UHFFFAOYSA-N 0.000 description 1
- XYWHYGLFDRVGMD-UHFFFAOYSA-N 1-[1-(4-ethoxyphenyl)-2-nitrobutyl]-4-methoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(CC)[N+]([O-])=O)C1=CC=C(OC)C=C1 XYWHYGLFDRVGMD-UHFFFAOYSA-N 0.000 description 1
- FJAIUMJCZSTDRG-UHFFFAOYSA-N 1-ethoxy-4-[1-(4-ethylsulfanylphenyl)-2-nitropropyl]benzene Chemical compound C1=CC(OCC)=CC=C1C(C(C)[N+]([O-])=O)C1=CC=C(SCC)C=C1 FJAIUMJCZSTDRG-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- XMHQACSAFILBHZ-UHFFFAOYSA-N 5-[1-(4-ethoxyphenyl)-2-nitrobutyl]-1,3-benzodioxole Chemical compound C(C)OC1=CC=C(C=C1)C(C(CC)[N+](=O)[O-])C1=CC2=C(C=C1)OCO2 XMHQACSAFILBHZ-UHFFFAOYSA-N 0.000 description 1
- 241000132121 Acaridae Species 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 241000258920 Chilopoda Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241000736227 Lucilia sericata Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 241000131095 Oniscidea Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- QVRVXSZKCXFBTE-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCCCNC(=O)C1=CC(C)=CC=C1OCCF QVRVXSZKCXFBTE-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- GBAPRSGLWUEXIR-UHFFFAOYSA-N nitromethanol Chemical compound OC[N+]([O-])=O GBAPRSGLWUEXIR-UHFFFAOYSA-N 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 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
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/56—Radicals substituted by sulfur atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/52—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPA236770 | 1970-08-31 | ||
| AUPA394771 | 1971-02-05 | ||
| AUPA401071 | 1971-02-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2142653A1 DE2142653A1 (de) | 1972-03-02 |
| DE2142653B2 DE2142653B2 (de) | 1978-10-26 |
| DE2142653C3 true DE2142653C3 (de) | 1979-06-21 |
Family
ID=27156957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2142653A Expired DE2142653C3 (de) | 1970-08-31 | 1971-08-25 | l,l-Bis-(subst-phenyl)-2-nitroalkane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Insektizide |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US3823192A (OSRAM) |
| AR (1) | AR193209A1 (OSRAM) |
| AT (1) | AT326949B (OSRAM) |
| BE (1) | BE772018A (OSRAM) |
| BR (1) | BR7105746D0 (OSRAM) |
| CA (2) | CA964270A (OSRAM) |
| CH (1) | CH555798A (OSRAM) |
| DD (1) | DD103128A5 (OSRAM) |
| DE (1) | DE2142653C3 (OSRAM) |
| FR (1) | FR2106226A5 (OSRAM) |
| GB (1) | GB1319029A (OSRAM) |
| HU (1) | HU163241B (OSRAM) |
| IL (1) | IL37477A (OSRAM) |
| NL (1) | NL7111683A (OSRAM) |
| SU (1) | SU439971A3 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL37477A (en) * | 1970-08-31 | 1974-10-22 | Commw Scient Ind Res Org | 1,1-diphenyl-2-nitropropanes,their preparation and use as insecticides |
| SE405724B (sv) * | 1973-02-05 | 1978-12-27 | Ciba Geigy Ag | Derivat av 1,1-difenyl-2-nitropropan resp butan med anvendning for skadedjursbekempning |
| US3950433A (en) * | 1973-02-05 | 1976-04-13 | Ciba-Geigy Corporation | 1-Phenyl-1-p-propargyloxyphenyl-2-nitro-ethane derivatives |
| NL7500478A (nl) * | 1974-01-21 | 1975-07-23 | Ciba Geigy | Werkwijze voor het bereiden van nieuwe difenylverbindingen. |
| US4004023A (en) * | 1975-10-01 | 1977-01-18 | Mobil Oil Corporation | 1-(4-Butylphenyl)-1-(3,4-methylenedioxyphenyl)-2-nitroalkanes and synergistic insecticidal mixtures therewith |
| US4357344A (en) * | 1979-03-29 | 1982-11-02 | The United States Of America As Represented By The Secretary Of Agriculture | Polybutylbenzylphenols and benzyl-3,4-methylenedioxybenzenes in insect population control |
| US4594360A (en) * | 1984-11-23 | 1986-06-10 | Iowa State University Research Foundation & Inc. | Chloronitroalkane insecticides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3095456A (en) * | 1960-05-23 | 1963-06-25 | Commerical Solvents Corp | Nitrosulfides and their corresponding sulfones |
| US3657357A (en) * | 1969-07-17 | 1972-04-18 | Commw Scient Ind Res Org | Insecticidal compounds and methods for their preparation |
| IL37477A (en) * | 1970-08-31 | 1974-10-22 | Commw Scient Ind Res Org | 1,1-diphenyl-2-nitropropanes,their preparation and use as insecticides |
-
1971
- 1971-08-09 IL IL37477A patent/IL37477A/xx unknown
- 1971-08-23 US US00174265A patent/US3823192A/en not_active Expired - Lifetime
- 1971-08-25 NL NL7111683A patent/NL7111683A/xx not_active Application Discontinuation
- 1971-08-25 DE DE2142653A patent/DE2142653C3/de not_active Expired
- 1971-08-25 AR AR237555A patent/AR193209A1/es active
- 1971-08-25 CH CH1245171A patent/CH555798A/xx not_active IP Right Cessation
- 1971-08-30 DD DD163433A patent/DD103128A5/xx unknown
- 1971-08-30 CA CA121,677A patent/CA964270A/en not_active Expired
- 1971-08-31 SU SU1758013A patent/SU439971A3/ru active
- 1971-08-31 BR BR5746/71A patent/BR7105746D0/pt unknown
- 1971-08-31 HU HUCO257A patent/HU163241B/hu unknown
- 1971-08-31 FR FR7131454A patent/FR2106226A5/fr not_active Expired
- 1971-08-31 GB GB4053671A patent/GB1319029A/en not_active Expired
- 1971-08-31 BE BE772018A patent/BE772018A/xx unknown
-
1973
- 1973-04-16 AT AT335773*7A patent/AT326949B/de not_active IP Right Cessation
- 1973-12-20 US US426533A patent/US3884938A/en not_active Expired - Lifetime
- 1973-12-20 US US426592A patent/US3864405A/en not_active Expired - Lifetime
-
1974
- 1974-07-23 CA CA205,410A patent/CA984840A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR193209A1 (es) | 1973-04-11 |
| AT326949B (de) | 1976-01-12 |
| ATA335773A (de) | 1975-03-15 |
| NL7111683A (OSRAM) | 1972-03-02 |
| GB1319029A (en) | 1973-05-31 |
| DD103128A5 (OSRAM) | 1974-01-12 |
| CA984840A (en) | 1976-03-02 |
| CA964270A (en) | 1975-03-11 |
| HU163241B (OSRAM) | 1973-07-28 |
| CH555798A (de) | 1974-11-15 |
| BR7105746D0 (pt) | 1973-04-17 |
| BE772018A (fr) | 1971-12-31 |
| US3884938A (en) | 1975-05-20 |
| IL37477A (en) | 1974-10-22 |
| IL37477A0 (en) | 1971-11-29 |
| FR2106226A5 (OSRAM) | 1972-04-28 |
| US3823192A (en) | 1974-07-09 |
| DE2142653B2 (de) | 1978-10-26 |
| DE2142653A1 (de) | 1972-03-02 |
| SU439971A3 (ru) | 1974-08-15 |
| US3864405A (en) | 1975-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |