DE1693200A1 - Schaedlingsbekaempfungsmittel - Google Patents
SchaedlingsbekaempfungsmittelInfo
- Publication number
- DE1693200A1 DE1693200A1 DE19621693200 DE1693200A DE1693200A1 DE 1693200 A1 DE1693200 A1 DE 1693200A1 DE 19621693200 DE19621693200 DE 19621693200 DE 1693200 A DE1693200 A DE 1693200A DE 1693200 A1 DE1693200 A1 DE 1693200A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- group
- substituted
- phenyl
- dinitro
- 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.)
- Pending
Links
- 241000607479 Yersinia pestis Species 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 79
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 239000004480 active ingredient Substances 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- -1 phenyl - Chemical class 0.000 claims description 20
- 239000000575 pesticide Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 239000004563 wettable powder Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 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 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 5
- 239000000443 aerosol Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
- 239000000428 dust Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
- 241000239290 Araneae Species 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 241000220225 Malus Species 0.000 description 20
- 240000008067 Cucumis sativus Species 0.000 description 17
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 12
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 230000000895 acaricidal effect Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000011343 solid material Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 241000228452 Venturia inaequalis Species 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000001103 potassium chloride Substances 0.000 description 6
- 235000011164 potassium chloride Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 5
- HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 description 5
- 241000896242 Podosphaera Species 0.000 description 5
- 206010039509 Scab Diseases 0.000 description 5
- 241001261167 Tegenaria domestica Species 0.000 description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 description 5
- 230000003151 ovacidal effect Effects 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241000221787 Erysiphe Species 0.000 description 4
- 241001337928 Podosphaera leucotricha Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical compound CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HXNGWMWUICJCDR-UHFFFAOYSA-N 2,4-dinitro-6-phenylphenol Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1C1=CC=CC=C1 HXNGWMWUICJCDR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241000500439 Plutella Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 244000153888 Tung Species 0.000 description 2
- RKFVGYIJOAKKCB-UHFFFAOYSA-M [N+](=O)([O-])C1=C([O-])C(=CC(=C1)[N+](=O)[O-])C(C)CC.[K+] Chemical compound [N+](=O)([O-])C1=C([O-])C(=CC(=C1)[N+](=O)[O-])C(C)CC.[K+] RKFVGYIJOAKKCB-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 238000003898 horticulture Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- IFNHKAQTGUVGEG-UHFFFAOYSA-M potassium 2-tert-butyl-4,6-dinitrophenolate Chemical compound [N+](=O)([O-])C1=CC(=C(C(=C1)[N+](=O)[O-])[O-])C(C)(C)C.[K+] IFNHKAQTGUVGEG-UHFFFAOYSA-M 0.000 description 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KUTXYDMRJSABJJ-UHFFFAOYSA-N (2,4-dinitro-6-phenylphenyl) methyl carbonate Chemical compound C(OC)(OC1=C(C=C(C=C1C1=CC=CC=C1)[N+](=O)[O-])[N+](=O)[O-])=O KUTXYDMRJSABJJ-UHFFFAOYSA-N 0.000 description 1
- NPQQOVRPKWHSDZ-UHFFFAOYSA-N (2-cyclohexyl-4,6-dinitrophenyl) ethyl carbonate Chemical compound C(OCC)(OC1=C(C=C(C=C1C1CCCCC1)[N+](=O)[O-])[N+](=O)[O-])=O NPQQOVRPKWHSDZ-UHFFFAOYSA-N 0.000 description 1
- IXNUTQCZWAHNPN-UHFFFAOYSA-N (2-tert-butyl-4,6-dinitrophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(C)(C)C IXNUTQCZWAHNPN-UHFFFAOYSA-N 0.000 description 1
- ICAKLTPCXSQPLL-UHFFFAOYSA-N (2-tert-butyl-4,6-dinitrophenyl) methyl carbonate Chemical compound COC(=O)OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(C)(C)C ICAKLTPCXSQPLL-UHFFFAOYSA-N 0.000 description 1
- NWTXMRBFLWLZJU-UHFFFAOYSA-N (3-butan-2-yl-2,4-dinitrophenyl) propan-2-yl carbonate Chemical compound C(OC(C)C)(OC1=C(C(=C(C=C1)[N+](=O)[O-])C(C)CC)[N+](=O)[O-])=O NWTXMRBFLWLZJU-UHFFFAOYSA-N 0.000 description 1
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- DVOCCVCLRHDYOB-UHFFFAOYSA-N 2,4-dinitro-6-octan-2-ylphenol Chemical compound CCCCCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O DVOCCVCLRHDYOB-UHFFFAOYSA-N 0.000 description 1
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
- HBYHYLBZPLCIEE-UHFFFAOYSA-N 2,4-dinitro-6-propan-2-ylphenol Chemical compound CC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O HBYHYLBZPLCIEE-UHFFFAOYSA-N 0.000 description 1
- FBDQKRAWGRTSAE-PGACXJNKSA-N 2-[(5z)-5-[(e)-3-(2-nitrophenyl)prop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)S\C1=C/C=C/C1=CC=CC=C1[N+]([O-])=O FBDQKRAWGRTSAE-PGACXJNKSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- NJBDTWSOYUZQPM-UHFFFAOYSA-N 4-tert-butyl-2,6-dinitrophenol Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 NJBDTWSOYUZQPM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- KNKMXIDIDVBHBS-UHFFFAOYSA-N C(OCC)(OC1=C(C=C(C=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-])=O Chemical compound C(OCC)(OC1=C(C=C(C=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-])=O KNKMXIDIDVBHBS-UHFFFAOYSA-N 0.000 description 1
- ANWOETLBEAOOEB-UHFFFAOYSA-N CCCCC(C([N+]([O-])=O)=C(C(C(C)CC)=C1C)OC(O)=O)=C1[N+]([O-])=O Chemical compound CCCCC(C([N+]([O-])=O)=C(C(C(C)CC)=C1C)OC(O)=O)=C1[N+]([O-])=O ANWOETLBEAOOEB-UHFFFAOYSA-N 0.000 description 1
- APLIDDGNNWQVTO-UHFFFAOYSA-N CCCCCCC(C([N+]([O-])=O)=C(C(C(C)(C)C)=C1)OC(O)=O)=C1[N+]([O-])=O Chemical compound CCCCCCC(C([N+]([O-])=O)=C(C(C(C)(C)C)=C1)OC(O)=O)=C1[N+]([O-])=O APLIDDGNNWQVTO-UHFFFAOYSA-N 0.000 description 1
- 101150026868 CHS1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-IGMARMGPSA-N Calcium-40 Chemical group [40Ca] OYPRJOBELJOOCE-IGMARMGPSA-N 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- QJYHUJAGJUHXJN-UHFFFAOYSA-N Dinex Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1C1CCCCC1 QJYHUJAGJUHXJN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000118205 Ovicides Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000736772 Uria Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- YSVGMCAHVAGCSS-UHFFFAOYSA-N [6-butan-2-yl-3-(2-ethylsulfanylethyl)-2,4-dinitrophenyl] hydrogen carbonate Chemical compound CCC(C)C1=CC(=C(C(=C1OC(=O)O)[N+](=O)[O-])CCSCC)[N+](=O)[O-] YSVGMCAHVAGCSS-UHFFFAOYSA-N 0.000 description 1
- ZUOWMTLQMWEQQE-UHFFFAOYSA-N [O-][N+](C(C=C1C2=CC=CC=C2)=CC([N+]([O-])=O)=C1OC(O)=O)=O Chemical compound [O-][N+](C(C=C1C2=CC=CC=C2)=CC([N+]([O-])=O)=C1OC(O)=O)=O ZUOWMTLQMWEQQE-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000002824 aphicidal effect Effects 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- BDOHQEPUDCPQMJ-UHFFFAOYSA-N bis(4-methoxy-3-nitrophenyl)methanone Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1C(=O)C1=CC=C(OC)C([N+]([O-])=O)=C1 BDOHQEPUDCPQMJ-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- CMIUEWSUNAYXCG-UHFFFAOYSA-N butyl phenyl carbonate Chemical compound CCCCOC(=O)OC1=CC=CC=C1 CMIUEWSUNAYXCG-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000004262 dental pulp cavity Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- RDQJDTOPBOAIKG-UHFFFAOYSA-N octan-2-yl carbonochloridate Chemical compound CCCCCCC(C)OC(Cl)=O RDQJDTOPBOAIKG-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000020004 porter Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 102000012498 secondary active transmembrane transporter activity proteins Human genes 0.000 description 1
- 108040003878 secondary active transmembrane transporter activity proteins Proteins 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/72—2-Mercaptobenzothiazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10501/61A GB1019451A (en) | 1961-03-22 | 1961-03-22 | Improvements in or relating to pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1693200A1 true DE1693200A1 (de) | 1971-04-08 |
Family
ID=9969009
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621693200 Pending DE1693200A1 (de) | 1961-03-22 | 1962-03-20 | Schaedlingsbekaempfungsmittel |
| DE19621793643 Pending DE1793643B1 (de) | 1961-03-22 | 1962-03-20 | Ysopropyl-2,4-dinitro-6-sek.-butylphenylcarbonat |
| DE1793719A Expired DE1793719C3 (de) | 1961-03-22 | 1962-03-20 | 2,4-Dinitro-6-(l-methyl-n-heptyl)- ' phenylcarbonate. Ausscheidung aus: 1693200 |
| DE19621793720 Pending DE1793720A1 (de) | 1961-03-22 | 1962-03-20 | Alkyl-2,4-dinitro-6-alkyl-phenylcarbonate |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621793643 Pending DE1793643B1 (de) | 1961-03-22 | 1962-03-20 | Ysopropyl-2,4-dinitro-6-sek.-butylphenylcarbonat |
| DE1793719A Expired DE1793719C3 (de) | 1961-03-22 | 1962-03-20 | 2,4-Dinitro-6-(l-methyl-n-heptyl)- ' phenylcarbonate. Ausscheidung aus: 1693200 |
| DE19621793720 Pending DE1793720A1 (de) | 1961-03-22 | 1962-03-20 | Alkyl-2,4-dinitro-6-alkyl-phenylcarbonate |
Country Status (6)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1070755A (en) * | 1964-08-07 | 1967-06-01 | Murphy Chemical Ltd | Improvements in or relating to 2,6-dinitro-4-alkylphenols and carbonates thereof |
| US3287211A (en) * | 1965-02-26 | 1966-11-22 | Stauffer Chemical Co | Controlling mites with certain alkyl-(2, 4-dinitrophenyl) carbonates |
| GB1190384A (en) * | 1966-09-09 | 1970-05-06 | Murphy Chemical Ltd | Dinitrodihalophenyl esters and fungicidal compositions containing them |
| RO55764A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-04-24 | 1974-01-03 | ||
| US3742010A (en) * | 1970-09-28 | 1973-06-26 | Ppg Industries Inc | Fluorinated carbonates |
| US3852464A (en) * | 1970-09-28 | 1974-12-03 | Ppg Industries Inc | Miticidal fluorinated carbonates |
| US4022609A (en) * | 1972-10-24 | 1977-05-10 | Ppg Industries, Inc. | Herbicidal fluorinated carbonates |
| US4113878A (en) * | 1974-09-12 | 1978-09-12 | Ppg Industries, Inc. | Control of pathogenic fungi with fluorinated carbonates |
| AU2003239994A1 (en) * | 2002-06-11 | 2003-12-22 | E.I. Du Pont De Nemours And Company | Mixtures of fused pyrimidinones and dinitrophenolic compounds useful for controlling powdery mildews |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3123522A (en) * | 1964-03-03 | Chxchs | ||
| US2335237A (en) * | 1940-10-10 | 1943-11-30 | Geigy Ag J R | Amino-hydroxynaphthalene sulphonic acids or their n-substitution products and a process for making the same |
| US2787631A (en) * | 1954-05-05 | 1957-04-02 | Columbia Southern Chem Corp | Carbonate preparation |
| BE572200A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-10-24 | |||
| DE1088757B (de) * | 1957-12-27 | 1960-09-08 | Hoechst Ag | Mittel zur selektiven Unkrautbekaempfung |
-
0
- NL NL276256D patent/NL276256A/xx unknown
-
1961
- 1961-03-22 GB GB10501/61A patent/GB1019451A/en not_active Expired
-
1962
- 1962-03-15 US US180013A patent/US3234260A/en not_active Expired - Lifetime
- 1962-03-20 DE DE19621693200 patent/DE1693200A1/de active Pending
- 1962-03-20 DE DE19621793643 patent/DE1793643B1/de active Pending
- 1962-03-20 DE DE1793719A patent/DE1793719C3/de not_active Expired
- 1962-03-20 DE DE19621793720 patent/DE1793720A1/de active Pending
- 1962-03-21 CH CH774366A patent/CH434862A/de unknown
- 1962-03-21 CH CH338262A patent/CH429757A/de unknown
- 1962-03-21 BR BR137336/62A patent/BR6237336D0/pt unknown
-
1971
- 1971-12-22 NL NL7117684A patent/NL7117684A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1793719A1 (de) | 1973-02-08 |
| DE1793720A1 (de) | 1973-01-11 |
| CH434862A (de) | 1967-04-30 |
| CH429757A (de) | 1967-02-15 |
| US3234260A (en) | 1966-02-08 |
| DE1793719B2 (de) | 1973-12-13 |
| GB1019451A (en) | 1966-02-09 |
| NL7117684A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-03-27 |
| DE1793719C3 (de) | 1974-07-18 |
| BR6237336D0 (pt) | 1973-06-28 |
| DE1793643B1 (de) | 1972-06-29 |
| NL276256A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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