DD296490A5 - Verfahren zur herstellung neuer amid-derivate - Google Patents
Verfahren zur herstellung neuer amid-derivate Download PDFInfo
- Publication number
- DD296490A5 DD296490A5 DD34272588A DD34272588A DD296490A5 DD 296490 A5 DD296490 A5 DD 296490A5 DD 34272588 A DD34272588 A DD 34272588A DD 34272588 A DD34272588 A DD 34272588A DD 296490 A5 DD296490 A5 DD 296490A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- carbon atoms
- carboxylic acid
- reaction
- ethyl acetate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001408 amides Chemical class 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 125000005109 alkynylthio group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000004970 halomethyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 abstract description 18
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 10
- 238000003898 horticulture Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
- 239000000203 mixture Substances 0.000 description 47
- 150000001875 compounds Chemical class 0.000 description 37
- -1 2,6-dimethylphenyl Chemical group 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
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- 201000010099 disease Diseases 0.000 description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
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- 230000000855 fungicidal effect Effects 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
- XFCIXMTULIAPOT-UHFFFAOYSA-N n-[cyano(furan-2-yl)methyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C)=C1C(=O)NC(C#N)C1=CC=CO1 XFCIXMTULIAPOT-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- 241000233614 Phytophthora Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
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- 230000001276 controlling effect Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
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- 238000009472 formulation Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- MQGBARXPCXAFRZ-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=NC(C)=C(C(O)=O)S1 MQGBARXPCXAFRZ-UHFFFAOYSA-N 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000208125 Nicotiana Species 0.000 description 4
- 241000233622 Phytophthora infestans Species 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
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- 206010039509 Scab Diseases 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
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- 239000012467 final product Substances 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- UBZBDSILDATCPA-UHFFFAOYSA-N 2,4-diethyl-1,3-thiazole-5-carbonyl chloride Chemical compound CCC1=NC(CC)=C(C(Cl)=O)S1 UBZBDSILDATCPA-UHFFFAOYSA-N 0.000 description 2
- JTOMQXXKQNNQIM-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carbonyl chloride Chemical compound CC1=NC(C)=C(C(Cl)=O)S1 JTOMQXXKQNNQIM-UHFFFAOYSA-N 0.000 description 2
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 2
- ZGNZEKQJACWPKW-UHFFFAOYSA-N 2-chloro-4-methyl-1,3-thiazole-5-carbonyl chloride Chemical compound CC=1N=C(Cl)SC=1C(Cl)=O ZGNZEKQJACWPKW-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 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 description 2
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- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 239000010949 copper Substances 0.000 description 2
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- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- QGDIJZMKEQCRBX-UHFFFAOYSA-N zinc;ethene Chemical group [Zn+2].[CH-]=C.[CH-]=C QGDIJZMKEQCRBX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26782787 | 1987-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD296490A5 true DD296490A5 (de) | 1991-12-05 |
Family
ID=17450165
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD34272588A DD296490A5 (de) | 1987-10-23 | 1988-10-24 | Verfahren zur herstellung neuer amid-derivate |
| DD88321035A DD283323A5 (de) | 1987-10-23 | 1988-10-24 | Fungizide zusammensetzung fuer die landwirtschaft und gartenbau |
| DD34272488A DD296484A5 (de) | 1987-10-23 | 1988-10-24 | Verfahren zur herstellung neuer amid-derivate |
| DD34272390A DD296401A5 (de) | 1987-10-23 | 1990-07-12 | Fungizide zusammensetzung |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88321035A DD283323A5 (de) | 1987-10-23 | 1988-10-24 | Fungizide zusammensetzung fuer die landwirtschaft und gartenbau |
| DD34272488A DD296484A5 (de) | 1987-10-23 | 1988-10-24 | Verfahren zur herstellung neuer amid-derivate |
| DD34272390A DD296401A5 (de) | 1987-10-23 | 1990-07-12 | Fungizide zusammensetzung |
Country Status (3)
| Country | Link |
|---|---|
| DD (4) | DD296490A5 (pl) |
| PL (2) | PL160608B1 (pl) |
| RO (2) | RO107654B1 (pl) |
-
1988
- 1988-10-22 PL PL27542688A patent/PL160608B1/pl unknown
- 1988-10-22 PL PL28139488A patent/PL162128B1/pl unknown
- 1988-10-24 DD DD34272588A patent/DD296490A5/de not_active IP Right Cessation
- 1988-10-24 DD DD88321035A patent/DD283323A5/de not_active IP Right Cessation
- 1988-10-24 RO RO14647088A patent/RO107654B1/ro unknown
- 1988-10-24 RO RO13562488A patent/RO102459B1/ro unknown
- 1988-10-24 DD DD34272488A patent/DD296484A5/de not_active IP Right Cessation
-
1990
- 1990-07-12 DD DD34272390A patent/DD296401A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL275426A1 (en) | 1990-03-19 |
| DD296401A5 (de) | 1991-12-05 |
| RO102459B1 (en) | 1992-07-01 |
| PL160608B1 (pl) | 1993-04-30 |
| PL162128B1 (pl) | 1993-09-30 |
| DD296484A5 (de) | 1991-12-05 |
| PL281394A1 (en) | 1990-05-14 |
| DD283323A5 (de) | 1990-10-10 |
| RO107654B1 (ro) | 1993-12-30 |
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| ENJ | Ceased due to non-payment of renewal fee |