CS217983B2 - Herbicide means - Google Patents
Herbicide means Download PDFInfo
- Publication number
- CS217983B2 CS217983B2 CS806310A CS631080A CS217983B2 CS 217983 B2 CS217983 B2 CS 217983B2 CS 806310 A CS806310 A CS 806310A CS 631080 A CS631080 A CS 631080A CS 217983 B2 CS217983 B2 CS 217983B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chloro
- align
- preservative
- trifluoromethyl
- herbicide
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 63
- 239000004009 herbicide Substances 0.000 title claims abstract description 45
- -1 2-chloro-4,5-disubstituted-thiazoles Chemical class 0.000 claims abstract description 26
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
- 229960001413 acetanilide Drugs 0.000 claims abstract description 7
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims abstract description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 52
- 239000003755 preservative agent Substances 0.000 claims description 51
- 230000002335 preservative effect Effects 0.000 claims description 46
- 230000001681 protective effect Effects 0.000 claims description 17
- 230000002195 synergetic effect Effects 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims 1
- WQWVQIVJGAOWDJ-UHFFFAOYSA-N 3-methoxy-n-phenylpropanamide Chemical compound COCCC(=O)NC1=CC=CC=C1 WQWVQIVJGAOWDJ-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 240000006394 Sorghum bicolor Species 0.000 abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 16
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 230000006378 damage Effects 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 208000027418 Wounds and injury Diseases 0.000 abstract description 2
- 208000014674 injury Diseases 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000002689 soil Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000008188 pellet Substances 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 13
- 239000003208 petroleum Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000011324 bead Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008061 acetanilides Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 3
- 239000005625 Tri-allate Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CARVBTDDTSNCMZ-UHFFFAOYSA-N [2-chloro-4-(trifluoromethyl)-1,3-thiazol-5-yl]methanol Chemical compound OCC=1SC(Cl)=NC=1C(F)(F)F CARVBTDDTSNCMZ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- STUXOONJFFCWIP-UHFFFAOYSA-N (2-chloro-4-propan-2-yl-1,3-thiazol-5-yl)methanol Chemical compound CC(C)C=1N=C(Cl)SC=1CO STUXOONJFFCWIP-UHFFFAOYSA-N 0.000 description 2
- IIHTWRADTMJZBN-UHFFFAOYSA-N 2-chloro-5-(methylsulfanylmethyl)-4-(trifluoromethyl)-1,3-thiazole Chemical compound CSCC=1SC(Cl)=NC=1C(F)(F)F IIHTWRADTMJZBN-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 2
- 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 2
- 239000005909 Kieselgur Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- BTLDLLBFXKAXIG-UHFFFAOYSA-N [2-chloro-4-(trifluoromethyl)-1,3-thiazol-5-yl]methanethiol Chemical compound FC(F)(F)C=1N=C(Cl)SC=1CS BTLDLLBFXKAXIG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- PDQRIMRBJSQRSL-UHFFFAOYSA-N di(propan-2-yl)carbamothioic s-acid Chemical compound CC(C)N(C(C)C)C(S)=O PDQRIMRBJSQRSL-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- IJOAPNOGRYXEDJ-UHFFFAOYSA-N ethyl 2-(2-chloro-4-methyl-1,3-thiazol-5-yl)acetate Chemical compound CCOC(=O)CC=1SC(Cl)=NC=1C IJOAPNOGRYXEDJ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- AGNNILFVQBALLT-UHFFFAOYSA-N (2-tert-butyl-1,3-thiazol-5-yl)methanol Chemical compound CC(C)(C)C1=NC=C(CO)S1 AGNNILFVQBALLT-UHFFFAOYSA-N 0.000 description 1
- FPGQANRWQGXSDR-UHFFFAOYSA-N (4-tert-butyl-2-chloro-1,3-thiazol-5-yl)methanol Chemical compound CC(C)(C)C=1N=C(Cl)SC=1CO FPGQANRWQGXSDR-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- CLLLODNOQBVIMS-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetic acid Chemical compound COCCOCC(O)=O CLLLODNOQBVIMS-UHFFFAOYSA-N 0.000 description 1
- XMXXKSHWUKNLPQ-UHFFFAOYSA-N 2-(trifluoromethyl)-1,3-thiazole Chemical compound FC(F)(F)C1=NC=CS1 XMXXKSHWUKNLPQ-UHFFFAOYSA-N 0.000 description 1
- PXLWZZVFMAXEKG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-4-(trifluoromethyl)-1,3-thiazole Chemical compound FC(F)(F)C=1N=C(Cl)SC=1CCl PXLWZZVFMAXEKG-UHFFFAOYSA-N 0.000 description 1
- PUMSFBKZJCOVOM-UHFFFAOYSA-N 2-chloro-5-(methoxymethyl)-4-(trifluoromethyl)-1,3-thiazole Chemical compound COCC=1SC(Cl)=NC=1C(F)(F)F PUMSFBKZJCOVOM-UHFFFAOYSA-N 0.000 description 1
- AIBFGDHRNLXZME-UHFFFAOYSA-N 2-chloro-5-(phenylmethoxymethyl)-4-(trifluoromethyl)-1,3-thiazole Chemical compound N1=C(Cl)SC(COCC=2C=CC=CC=2)=C1C(F)(F)F AIBFGDHRNLXZME-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 208000003643 Callosities Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 244000060234 Gmelina philippensis Species 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000171263 Ribes grossularia Species 0.000 description 1
- 235000002357 Ribes grossularia Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- GPSDUYCMHWRUMT-UHFFFAOYSA-N [2-chloro-4-(4-chlorophenyl)-1,3-thiazol-5-yl]methanol Chemical compound S1C(Cl)=NC(C=2C=CC(Cl)=CC=2)=C1CO GPSDUYCMHWRUMT-UHFFFAOYSA-N 0.000 description 1
- BYIPNXQLZYJURB-UHFFFAOYSA-N [2-chloro-4-(4-fluorophenyl)-1,3-thiazol-5-yl]methanol Chemical compound S1C(Cl)=NC(C=2C=CC(F)=CC=2)=C1CO BYIPNXQLZYJURB-UHFFFAOYSA-N 0.000 description 1
- DEAPNOZQUXZPIV-UHFFFAOYSA-N [2-chloro-4-(trifluoromethyl)-1,3-thiazol-5-yl]methyl methanesulfonate Chemical compound CS(=O)(=O)OCC=1SC(Cl)=NC=1C(F)(F)F DEAPNOZQUXZPIV-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- QEZIBLVBXQCOTD-UHFFFAOYSA-N ethyl 2-(2-amino-4-methyl-1,3-thiazol-5-yl)acetate Chemical compound CCOC(=O)CC=1SC(N)=NC=1C QEZIBLVBXQCOTD-UHFFFAOYSA-N 0.000 description 1
- WAWHIWRJYDQIFN-UHFFFAOYSA-N ethyl 2-chloro-4-(4-chlorophenyl)-1,3-thiazole-5-carboxylate Chemical compound S1C(Cl)=NC(C=2C=CC(Cl)=CC=2)=C1C(=O)OCC WAWHIWRJYDQIFN-UHFFFAOYSA-N 0.000 description 1
- WMYRJPQYRWMTGK-UHFFFAOYSA-N ethyl 2-chloro-4-(4-fluorophenyl)-1,3-thiazole-5-carboxylate Chemical compound S1C(Cl)=NC(C=2C=CC(F)=CC=2)=C1C(=O)OCC WMYRJPQYRWMTGK-UHFFFAOYSA-N 0.000 description 1
- RLZUPBSTNNZDDH-UHFFFAOYSA-N ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(Cl)=NC=1C(F)(F)F RLZUPBSTNNZDDH-UHFFFAOYSA-N 0.000 description 1
- XVCUUXCJAKBPKJ-UHFFFAOYSA-N ethyl 4-tert-butyl-2-chloro-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(Cl)=NC=1C(C)(C)C XVCUUXCJAKBPKJ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- HUVWULNCGBXDRQ-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(CCCl)CCCl)C=C1 HUVWULNCGBXDRQ-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KEAYESYHFKHZAL-OUBTZVSYSA-N sodium-24 Chemical compound [24Na] KEAYESYHFKHZAL-OUBTZVSYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003470 sulfuric acid monoesters Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GLUDYSUVZMFKLB-UHFFFAOYSA-N tert-butyl 1,3-thiazole-5-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CN=CS1 GLUDYSUVZMFKLB-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/080,751 US4284426A (en) | 1979-10-01 | 1979-10-01 | 2-Chloro-4,5-disubstituted-thiazoles useful as herbicidal safeners |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS217983B2 true CS217983B2 (en) | 1983-02-25 |
Family
ID=22159377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS806310A CS217983B2 (en) | 1979-10-01 | 1980-09-18 | Herbicide means |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4284426A (no) |
| EP (1) | EP0027019B1 (no) |
| JP (1) | JPS5663971A (no) |
| KR (1) | KR840001620B1 (no) |
| AR (1) | AR226191A1 (no) |
| AT (1) | ATE2523T1 (no) |
| AU (1) | AU531152B2 (no) |
| BR (1) | BR8006284A (no) |
| CA (1) | CA1150273A (no) |
| CS (1) | CS217983B2 (no) |
| DE (1) | DE3062055D1 (no) |
| DK (1) | DK413480A (no) |
| ES (1) | ES8106897A1 (no) |
| IL (1) | IL61178A (no) |
| IN (1) | IN152196B (no) |
| MX (1) | MX6024E (no) |
| MY (1) | MY8600064A (no) |
| NO (1) | NO152934C (no) |
| NZ (1) | NZ195101A (no) |
| PL (1) | PL126545B1 (no) |
| RO (2) | RO81054A (no) |
| ZA (1) | ZA806029B (no) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4437876A (en) | 1980-04-14 | 1984-03-20 | Monsanto Company | 2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4437875A (en) | 1980-04-14 | 1984-03-20 | Monsanto Company | 2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4602454A (en) * | 1978-05-15 | 1986-07-29 | Monsanto Company | 2,4-disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4602937A (en) * | 1978-05-15 | 1986-07-29 | Monsanto Company | 2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4586948A (en) * | 1981-04-22 | 1986-05-06 | Monsanto Company | 2,4-disubstituted-5-thiazole-carboxylic acids and derivatives |
| IT1174454B (it) * | 1984-01-06 | 1987-07-01 | Montedison Spa | Composti ad attivita'antidotica per la difesa di culture agrarie dall'azione di erbicidi non seletivi |
| US5000775A (en) * | 1985-12-31 | 1991-03-19 | Monsanto Company | 2-amino-4,5-disubstituted-oxazole/thiazole compounds as herbicide antidotes |
| IL103586A (en) * | 1991-10-30 | 1997-09-30 | Astra Ab | Process for the preparation of 4-methyl-5- (2-chloroethyl)-thiazole and analogues thereof |
| US6737382B1 (en) | 2002-10-23 | 2004-05-18 | Nippon Soda Co. Ltd. | Insecticidal aminothiazole derivatives |
| US6617341B1 (en) | 2002-12-30 | 2003-09-09 | Nippon Soda Co. Ltd. | Insecticidal 2-iminothiazole derivatives |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2139570A (en) * | 1935-05-02 | 1938-12-06 | Winthrop Chem Co Inc | Thiazole compounds and manufacture thereof |
| US2186420A (en) * | 1937-12-04 | 1940-01-09 | Goodrich Co B F | Process for the manufacture of mercaptothiazoles |
| US2392935A (en) * | 1943-06-21 | 1946-01-15 | Goodrich Co B F | Purification of mercaptothiazoles |
| US2500142A (en) * | 1947-04-24 | 1950-03-07 | Gen Aniline & Film Corp | Thio-ether substituted thiazoles and selenazoles and process of preparing the same |
| US2776976A (en) * | 1952-10-21 | 1957-01-08 | Monsanto Chemicals | Halogen substituted unsaturated thiazolylthioethers |
| US3031457A (en) * | 1955-09-28 | 1962-04-24 | Charonnat Solange Costes | Salts of 4-methyl-5 (beta-halogenoethyl)-thiazole and certain sulfonic acids |
| DE1187620B (de) | 1963-07-31 | 1965-02-25 | Basf Ag | Verfahren zur Herstellung von Carbonsaeurechloriden der Thiazolreihe |
| US3536727A (en) * | 1966-12-22 | 1970-10-27 | Wyeth John & Brother Ltd | Alpha-(2-arylthiazol-4-yl) lower fatty acids and derivatives |
| USRE27506E (en) * | 1971-05-18 | 1972-10-10 | Certain tfflozolylurea compounds | |
| BE790569A (fr) * | 1971-10-27 | 1973-04-26 | Syntex Corp | Agents cardiovasculaires a base de thiazoles |
| DE2213865C3 (de) * | 1972-03-22 | 1981-01-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Chlorthiazolen |
| US4124372A (en) * | 1973-05-02 | 1978-11-07 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| GB1403876A (en) * | 1973-05-04 | 1975-08-28 | Stauffer Chemical Co | Thiazolidine derivatives and their use as herbicide antidotes |
-
1979
- 1979-10-01 US US06/080,751 patent/US4284426A/en not_active Expired - Lifetime
-
1980
- 1980-09-18 CS CS806310A patent/CS217983B2/cs unknown
- 1980-09-26 CA CA000361153A patent/CA1150273A/en not_active Expired
- 1980-09-29 EP EP80303421A patent/EP0027019B1/en not_active Expired
- 1980-09-29 AT AT80303421T patent/ATE2523T1/de not_active IP Right Cessation
- 1980-09-29 ES ES495440A patent/ES8106897A1/es not_active Expired
- 1980-09-29 DE DE8080303421T patent/DE3062055D1/de not_active Expired
- 1980-09-30 ZA ZA00806029A patent/ZA806029B/xx unknown
- 1980-09-30 IL IL61178A patent/IL61178A/xx unknown
- 1980-09-30 MX MX809066U patent/MX6024E/es unknown
- 1980-09-30 IN IN1109/CAL/80A patent/IN152196B/en unknown
- 1980-09-30 PL PL1980227011A patent/PL126545B1/pl unknown
- 1980-09-30 DK DK413480A patent/DK413480A/da not_active Application Discontinuation
- 1980-09-30 NZ NZ195101A patent/NZ195101A/xx unknown
- 1980-09-30 RO RO80102249A patent/RO81054A/ro unknown
- 1980-09-30 NO NO802888A patent/NO152934C/no unknown
- 1980-09-30 RO RO110453A patent/RO86357B1/ro unknown
- 1980-09-30 AU AU62824/80A patent/AU531152B2/en not_active Ceased
- 1980-09-30 KR KR1019800003808A patent/KR840001620B1/ko active IP Right Grant
- 1980-09-30 AR AR282704A patent/AR226191A1/es active
- 1980-09-30 JP JP13535980A patent/JPS5663971A/ja active Pending
- 1980-09-30 BR BR8006284A patent/BR8006284A/pt unknown
-
1986
- 1986-12-30 MY MY64/86A patent/MY8600064A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO802888L (no) | 1981-04-02 |
| EP0027019A1 (en) | 1981-04-15 |
| DE3062055D1 (en) | 1983-03-24 |
| ZA806029B (en) | 1981-11-25 |
| IN152196B (no) | 1983-11-12 |
| CA1150273A (en) | 1983-07-19 |
| KR840001620B1 (ko) | 1984-10-12 |
| RO86357B1 (ro) | 1985-03-31 |
| IL61178A (en) | 1984-10-31 |
| US4284426A (en) | 1981-08-18 |
| JPS5663971A (en) | 1981-05-30 |
| AU531152B2 (en) | 1983-08-11 |
| MX6024E (es) | 1984-09-24 |
| AR226191A1 (es) | 1982-06-15 |
| ATE2523T1 (de) | 1983-03-15 |
| EP0027019B1 (en) | 1983-02-16 |
| PL227011A1 (no) | 1981-12-23 |
| DK413480A (da) | 1981-04-02 |
| AU6282480A (en) | 1981-04-09 |
| NO152934C (no) | 1985-12-18 |
| PL126545B1 (en) | 1983-08-31 |
| NZ195101A (en) | 1983-06-17 |
| ES495440A0 (es) | 1981-09-01 |
| NO152934B (no) | 1985-09-09 |
| ES8106897A1 (es) | 1981-09-01 |
| KR830003456A (ko) | 1983-06-20 |
| MY8600064A (en) | 1986-12-31 |
| RO86357A2 (ro) | 1985-03-15 |
| BR8006284A (pt) | 1981-04-07 |
| RO81054A (ro) | 1983-06-01 |
| RO81054B (ro) | 1983-05-30 |
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