BR9905751B1 - composto de dipeptìdeo, uso do mesmo, composições fungicidas, processo para a preparação das mesmas, e, processo para combater infecções por fungos. - Google Patents
composto de dipeptìdeo, uso do mesmo, composições fungicidas, processo para a preparação das mesmas, e, processo para combater infecções por fungos. Download PDFInfo
- Publication number
- BR9905751B1 BR9905751B1 BRPI9905751-4A BR9905751A BR9905751B1 BR 9905751 B1 BR9905751 B1 BR 9905751B1 BR 9905751 A BR9905751 A BR 9905751A BR 9905751 B1 BR9905751 B1 BR 9905751B1
- Authority
- BR
- Brazil
- Prior art keywords
- methyl
- corresponds
- amino
- compound
- propanoate
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 114
- 239000000203 mixture Substances 0.000 title claims description 37
- 108010016626 Dipeptides Proteins 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 19
- 230000000855 fungicidal effect Effects 0.000 title claims description 16
- 206010017533 Fungal infection Diseases 0.000 title description 2
- 208000031888 Mycoses Diseases 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- -1 phenylacetyl Chemical group 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 4
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 claims description 4
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 claims description 4
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 claims description 4
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 239000005734 Benalaxyl Substances 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 230000009418 agronomic effect Effects 0.000 claims description 3
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 claims description 3
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 3
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 2
- OQEBBZSWEGYTPG-GSVOUGTGSA-N (3r)-3-aminobutanoic acid Chemical compound C[C@@H](N)CC(O)=O OQEBBZSWEGYTPG-GSVOUGTGSA-N 0.000 claims description 2
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 claims description 2
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-Aminobutanoic acid Natural products CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 claims description 2
- QDUDFMMPZWYGFP-UHFFFAOYSA-N 3-anilino-5-methyl-2-methylsulfanyl-5-phenylimidazolidin-4-one Chemical compound CSC1NC(C)(C=2C=CC=CC=2)C(=O)N1NC1=CC=CC=C1 QDUDFMMPZWYGFP-UHFFFAOYSA-N 0.000 claims description 2
- QQMFZDGGOOVCBD-UHFFFAOYSA-N CC[S+]1N=C(C(Cl)(Cl)Cl)N=C1OC1=NC(C(Cl)(Cl)Cl)=N[S+]1CC Chemical compound CC[S+]1N=C(C(Cl)(Cl)Cl)N=C1OC1=NC(C(Cl)(Cl)Cl)=N[S+]1CC QQMFZDGGOOVCBD-UHFFFAOYSA-N 0.000 claims description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 2
- 239000005750 Copper hydroxide Substances 0.000 claims description 2
- 239000005752 Copper oxychloride Substances 0.000 claims description 2
- 239000005764 Dithianon Substances 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000005769 Etridiazole Substances 0.000 claims description 2
- 239000005772 Famoxadone Substances 0.000 claims description 2
- 239000005780 Fluazinam Substances 0.000 claims description 2
- 239000005789 Folpet Substances 0.000 claims description 2
- 239000005797 Iprovalicarb Substances 0.000 claims description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 2
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 claims description 2
- 239000005802 Mancozeb Substances 0.000 claims description 2
- 239000005805 Mepanipyrim Substances 0.000 claims description 2
- 239000005807 Metalaxyl Substances 0.000 claims description 2
- XFOXDUJCOHBXRC-UHFFFAOYSA-N N-Ethyl-N-methyl-4-(trifluoromethyl)-2-(3,4-dimethoxyphenyl)benzamide Chemical compound CCN(C)C(=O)C1=CC=C(C(F)(F)F)C=C1C1=CC=C(OC)C(OC)=C1 XFOXDUJCOHBXRC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005819 Potassium phosphonate Substances 0.000 claims description 2
- 239000005821 Propamocarb Substances 0.000 claims description 2
- 239000005823 Propineb Substances 0.000 claims description 2
- 239000005828 Pyrimethanil Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000011717 all-trans-retinol Substances 0.000 claims description 2
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 claims description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 2
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- YXXXKCDYKKSZHL-UHFFFAOYSA-M dipotassium;dioxido(oxo)phosphanium Chemical compound [K+].[K+].[O-][P+]([O-])=O YXXXKCDYKKSZHL-UHFFFAOYSA-M 0.000 claims description 2
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 claims description 2
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- VUERQRKTYBIULR-UHFFFAOYSA-N fosetyl Chemical compound CCOP(O)=O VUERQRKTYBIULR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- QJPWUUJVYOJNMH-UHFFFAOYSA-N homoserine lactone Chemical compound NC1CCOC1=O QJPWUUJVYOJNMH-UHFFFAOYSA-N 0.000 claims description 2
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 claims description 2
- 229920000940 maneb Polymers 0.000 claims description 2
- AWTNYZMRDAMOGW-UHFFFAOYSA-L manganese(2+);dicarbamodithioate Chemical compound [Mn+2].NC([S-])=S.NC([S-])=S AWTNYZMRDAMOGW-UHFFFAOYSA-L 0.000 claims description 2
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims description 2
- YQYKFSVTESXLFN-UHFFFAOYSA-N o-methyl 1,2,3-benzothiadiazole-7-carbothioate Chemical compound COC(=S)C1=CC=CC2=C1SN=N2 YQYKFSVTESXLFN-UHFFFAOYSA-N 0.000 claims description 2
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 claims description 2
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 2
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 claims description 2
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 claims description 2
- 238000009331 sowing Methods 0.000 claims description 2
- MPTYXKQJSCYQPW-UHFFFAOYSA-N 3-(dimethylamino)hexyl carbamate Chemical compound CCCC(N(C)C)CCOC(N)=O MPTYXKQJSCYQPW-UHFFFAOYSA-N 0.000 claims 1
- PXHWLMUSVTVOMH-UHFFFAOYSA-N 4-chloro-2-cyano-N,N-bis(methylamino)-5-(4-methylphenyl)imidazole-1-sulfonamide Chemical compound C(#N)C=1N(C(=C(N=1)Cl)C1=CC=C(C=C1)C)S(N(NC)NC)(=O)=O PXHWLMUSVTVOMH-UHFFFAOYSA-N 0.000 claims 1
- OGNIPSDRUNTVCH-UHFFFAOYSA-L CC=C.SC(=S)N[Zn]NC(S)=S Chemical compound CC=C.SC(=S)N[Zn]NC(S)=S OGNIPSDRUNTVCH-UHFFFAOYSA-L 0.000 claims 1
- TXSULMYZLWFIAT-UHFFFAOYSA-N carbamodithioic acid;ethene Chemical compound C=C.NC(S)=S TXSULMYZLWFIAT-UHFFFAOYSA-N 0.000 claims 1
- 230000007794 irritation Effects 0.000 claims 1
- WJZHMLNIAZSFDO-UHFFFAOYSA-N manganese zinc Chemical compound [Mn].[Zn] WJZHMLNIAZSFDO-UHFFFAOYSA-N 0.000 claims 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 19
- 239000000575 pesticide Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000002253 acid 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
- 229960004295 valine Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 229960001701 chloroform Drugs 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000013379 physicochemical characterization Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000001576 beta-amino acids Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000004474 valine Substances 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-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
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 241001223281 Peronospora Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1998MI002583A IT1303800B1 (it) | 1998-11-30 | 1998-11-30 | Composti dipeptidici aventi elevata attivita' fungicida e loroutilizzo agronomico. |
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| Publication Number | Publication Date |
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| BR9905751A BR9905751A (pt) | 2000-08-29 |
| BR9905751B1 true BR9905751B1 (pt) | 2011-09-06 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1270882B (it) * | 1993-10-05 | 1997-05-13 | Isagro Srl | Oligopeptidi ad attivita' fungicida |
| IT1271026B (it) * | 1994-10-21 | 1997-05-26 | Isagro Ricerca Srl | Derivati dell'acido b-amminopropionico ad attivita' fungicida |
| AU677726B2 (en) * | 1994-10-27 | 1997-05-01 | Ihara Chemical Industry Co. Ltd. | Amino acid amide derivative, process for producing the same, and agrohorticultural bactericide |
| DE69718835T2 (de) * | 1996-12-19 | 2003-12-24 | Isagro S.P.A., Mailand/Milano | Verfahren zur Herstellung von (N-Phenylacetyl-N-2,6-xylyl)methyl Alaninat |
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1998
- 1998-11-30 IT IT1998MI002583A patent/IT1303800B1/it active
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1999
- 1999-11-23 AR ARP990105968A patent/AR021380A1/es active IP Right Grant
- 1999-11-24 EP EP99203955A patent/EP1028125B1/en not_active Expired - Lifetime
- 1999-11-24 PT PT99203955T patent/PT1028125E/pt unknown
- 1999-11-24 SI SI9930537T patent/SI1028125T1/xx unknown
- 1999-11-24 ES ES99203955T patent/ES2213979T3/es not_active Expired - Lifetime
- 1999-11-24 AT AT99203955T patent/ATE258557T1/de active
- 1999-11-24 DK DK99203955T patent/DK1028125T3/da active
- 1999-11-24 DE DE69914450T patent/DE69914450T2/de not_active Expired - Lifetime
- 1999-11-24 AU AU60628/99A patent/AU756519B2/en not_active Expired
- 1999-11-25 NZ NZ501346A patent/NZ501346A/xx not_active IP Right Cessation
- 1999-11-26 BR BRPI9905751-4A patent/BR9905751B1/pt not_active IP Right Cessation
- 1999-11-29 US US09/450,950 patent/US6448228B1/en not_active Expired - Lifetime
- 1999-11-30 JP JP34095499A patent/JP4498511B2/ja not_active Expired - Lifetime
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2012
- 2012-10-12 BE BE2012C041C patent/BE2012C041I2/fr unknown
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2016
- 2016-11-16 LU LU93311C patent/LU93311I2/fr unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| IT1303800B1 (it) | 2001-02-23 |
| EP1028125A1 (en) | 2000-08-16 |
| SI1028125T1 (en) | 2004-06-30 |
| DK1028125T3 (da) | 2004-06-01 |
| ATE258557T1 (de) | 2004-02-15 |
| DE69914450D1 (de) | 2004-03-04 |
| US6448228B1 (en) | 2002-09-10 |
| BE2012C041I2 (cg-RX-API-DMAC7.html) | 2019-03-05 |
| FR19C1051I1 (cg-RX-API-DMAC7.html) | 2019-11-10 |
| LU93311I2 (fr) | 2017-01-26 |
| ES2213979T3 (es) | 2004-09-01 |
| NZ501346A (en) | 2000-10-27 |
| DE69914450T2 (de) | 2004-11-04 |
| JP4498511B2 (ja) | 2010-07-07 |
| NL350094I2 (nl) | 2019-12-11 |
| NL350094I1 (nl) | 2019-05-01 |
| ITMI982583A1 (it) | 2000-05-30 |
| JP2000198797A (ja) | 2000-07-18 |
| EP1028125B1 (en) | 2004-01-28 |
| AR021380A1 (es) | 2002-07-17 |
| PT1028125E (pt) | 2004-05-31 |
| AU756519B2 (en) | 2003-01-16 |
| FR19C1051I2 (fr) | 2020-09-04 |
| AU6062899A (en) | 2000-06-01 |
| BR9905751A (pt) | 2000-08-29 |
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