CH441270A - Verfahren zur Herstellung von Amidsäureestern und eine Anwendung derselben - Google Patents
Verfahren zur Herstellung von Amidsäureestern und eine Anwendung derselbenInfo
- Publication number
- CH441270A CH441270A CH210863A CH210863A CH441270A CH 441270 A CH441270 A CH 441270A CH 210863 A CH210863 A CH 210863A CH 210863 A CH210863 A CH 210863A CH 441270 A CH441270 A CH 441270A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- carbon atoms
- acid
- methyl ester
- esters
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 27
- 150000002148 esters Chemical class 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 maleamic acid compound Chemical class 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical class NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- BHEHHFCLZZCBFS-UHFFFAOYSA-N methyl (Z)-4-(decylamino)-4-oxobut-2-enoate Chemical compound C(CCCCCCCCC)NC(C=C/C(=O)OC)=O BHEHHFCLZZCBFS-UHFFFAOYSA-N 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 150000004702 methyl esters Chemical class 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- HXXJDJHHLXEVBZ-SREVYHEPSA-N (z)-4-(hexylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCNC(=O)\C=C/C(O)=O HXXJDJHHLXEVBZ-SREVYHEPSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- WIFBVQAEMGBNJR-UHFFFAOYSA-N methyl (Z)-4-(2,5-dichloroanilino)-4-oxobut-2-enoate Chemical compound ClC1=C(C=C(C=C1)Cl)NC(C=C/C(=O)OC)=O WIFBVQAEMGBNJR-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001069 nematicidal effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- QLLQFUHLCIKPCF-FPLPWBNLSA-N (Z)-N'-hexyl-N'-methylbut-2-enediamide Chemical compound CCCCCCN(C)C(=O)\C=C/C(N)=O QLLQFUHLCIKPCF-FPLPWBNLSA-N 0.000 description 2
- URLVICRNTDKOAU-SREVYHEPSA-N (Z)-N'-hexylbut-2-enediamide Chemical compound C(CCCCC)NC(\C=C/C(=O)N)=O URLVICRNTDKOAU-SREVYHEPSA-N 0.000 description 2
- WHZLCOICKHIPRL-SREVYHEPSA-N (z)-4-anilino-4-oxobut-2-enoic acid Chemical class OC(=O)\C=C/C(=O)NC1=CC=CC=C1 WHZLCOICKHIPRL-SREVYHEPSA-N 0.000 description 2
- NRYGCICLBPJWHA-KHPPLWFESA-N (z)-n'-decylbut-2-enediamide Chemical compound CCCCCCCCCCNC(=O)\C=C/C(N)=O NRYGCICLBPJWHA-KHPPLWFESA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- 235000007238 Secale cereale Nutrition 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
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- YFYLRPBKNXFGQQ-KTKRTIGZSA-N methyl (z)-4-(octylamino)-4-oxobut-2-enoate Chemical compound CCCCCCCCNC(=O)\C=C/C(=O)OC YFYLRPBKNXFGQQ-KTKRTIGZSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HXXJDJHHLXEVBZ-VOTSOKGWSA-N (e)-4-(hexylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCNC(=O)\C=C\C(O)=O HXXJDJHHLXEVBZ-VOTSOKGWSA-N 0.000 description 1
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 description 1
- FBTQVXSNFILAQY-WAYWQWQTSA-N (z)-4-(4-chloroanilino)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)NC1=CC=C(Cl)C=C1 FBTQVXSNFILAQY-WAYWQWQTSA-N 0.000 description 1
- PSNAHWRZQOSIQE-KHPPLWFESA-N (z)-4-(decylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCNC(=O)\C=C/C(O)=O PSNAHWRZQOSIQE-KHPPLWFESA-N 0.000 description 1
- BZVFXWPGZHIDSJ-WAYWQWQTSA-N (z)-4-(diethylamino)-4-oxobut-2-enoic acid Chemical compound CCN(CC)C(=O)\C=C/C(O)=O BZVFXWPGZHIDSJ-WAYWQWQTSA-N 0.000 description 1
- NWODYZCQADERLP-HNENSFHCSA-N (z)-4-(octadecylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)\C=C/C(O)=O NWODYZCQADERLP-HNENSFHCSA-N 0.000 description 1
- PTDZPBBGCHHKCY-HJWRWDBZSA-N (z)-4-(octylamino)-4-oxobut-2-enoic acid Chemical compound CCCCCCCCNC(=O)\C=C/C(O)=O PTDZPBBGCHHKCY-HJWRWDBZSA-N 0.000 description 1
- FQDVWOGLBOAPCP-PFONDFGASA-N (z)-4-oxo-4-(tetradecylamino)but-2-enoic acid Chemical compound CCCCCCCCCCCCCCNC(=O)\C=C/C(O)=O FQDVWOGLBOAPCP-PFONDFGASA-N 0.000 description 1
- ZLYYJUJDFKGVKB-UPHRSURJSA-N (z)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C/C(Cl)=O ZLYYJUJDFKGVKB-UPHRSURJSA-N 0.000 description 1
- JOOWUNKQFDHPRH-IHWYPQMZSA-N (z)-n'-methylbut-2-enediamide Chemical compound CNC(=O)\C=C/C(N)=O JOOWUNKQFDHPRH-IHWYPQMZSA-N 0.000 description 1
- DXVPKJKXBRHPTD-HJWRWDBZSA-N (z)-n'-octylbut-2-enediamide Chemical compound CCCCCCCCNC(=O)\C=C/C(N)=O DXVPKJKXBRHPTD-HJWRWDBZSA-N 0.000 description 1
- WBEJYOJJBDISQU-UHFFFAOYSA-N 1,2-Dibromo-3-chloropropane Chemical compound ClCC(Br)CBr WBEJYOJJBDISQU-UHFFFAOYSA-N 0.000 description 1
- HTHHBTMNLHMBHQ-UHFFFAOYSA-N 10-(1-azabicyclo[2.2.2]octan-3-yl)-n,n-dimethylphenothiazine-2-sulfonamide Chemical compound C1N(CC2)CCC2C1N1C2=CC=CC=C2SC2=CC=C(S(=O)(=O)N(C)C)C=C21 HTHHBTMNLHMBHQ-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- NYCGBSAZWOCXNH-UHFFFAOYSA-N 4-(2,4-dichloroanilino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC1=CC=C(Cl)C=C1Cl NYCGBSAZWOCXNH-UHFFFAOYSA-N 0.000 description 1
- XILORGWKMLOGKF-UHFFFAOYSA-N 4-(diethylamino)-4-oxobutanoic acid Chemical compound CCN(CC)C(=O)CCC(O)=O XILORGWKMLOGKF-UHFFFAOYSA-N 0.000 description 1
- VHSXMWPTPBCNHB-UHFFFAOYSA-N 4-(dipropylamino)-4-oxobutanoic acid Chemical compound CCCN(CCC)C(=O)CCC(O)=O VHSXMWPTPBCNHB-UHFFFAOYSA-N 0.000 description 1
- XYMWLIJFLBQNMI-UHFFFAOYSA-N 5-(diethylamino)-5-oxopentanoic acid Chemical compound CCN(CC)C(=O)CCCC(O)=O XYMWLIJFLBQNMI-UHFFFAOYSA-N 0.000 description 1
- OSFOQQNTRFDYIB-UHFFFAOYSA-N 5-(dipropylamino)-5-oxopentanoic acid Chemical compound CCCN(CCC)C(=O)CCCC(O)=O OSFOQQNTRFDYIB-UHFFFAOYSA-N 0.000 description 1
- BFUVSUPYGZQRAJ-UHFFFAOYSA-N 6-(diethylamino)-6-oxohexanoic acid Chemical compound CCN(CC)C(=O)CCCCC(O)=O BFUVSUPYGZQRAJ-UHFFFAOYSA-N 0.000 description 1
- QWYMIHAIXQQBLJ-UHFFFAOYSA-N 6-(dipropylamino)-6-oxohexanoic acid Chemical compound CCCN(CCC)C(=O)CCCCC(O)=O QWYMIHAIXQQBLJ-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000499339 Botrytis allii Species 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000244205 Panagrellus Species 0.000 description 1
- 241000122123 Penicillium italicum Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- NOIZJQMZRULFFO-UHFFFAOYSA-N adipamic acid Chemical class NC(=O)CCCCC(O)=O NOIZJQMZRULFFO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- HCSASYPHUDIUOV-UHFFFAOYSA-N ethyl (Z)-4-anilino-4-oxobut-2-enoate Chemical compound C(C=C/C(=O)NC1=CC=CC=C1)(=O)OCC HCSASYPHUDIUOV-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- IUYQKSWXZBCERT-UHFFFAOYSA-N methyl (Z)-4-oxo-4-(tetradecylamino)but-2-enoate Chemical compound C(CCCCCCCCCCCCC)NC(C=C/C(=O)OC)=O IUYQKSWXZBCERT-UHFFFAOYSA-N 0.000 description 1
- FITKKIPJKCHMGM-SREVYHEPSA-N methyl (z)-4-(4-chloroanilino)-4-oxobut-2-enoate Chemical compound COC(=O)\C=C/C(=O)NC1=CC=C(Cl)C=C1 FITKKIPJKCHMGM-SREVYHEPSA-N 0.000 description 1
- QOBPBYRWOYAVON-YPKPFQOOSA-N methyl (z)-4-(dodecylamino)-4-oxobut-2-enoate Chemical compound CCCCCCCCCCCCNC(=O)\C=C/C(=O)OC QOBPBYRWOYAVON-YPKPFQOOSA-N 0.000 description 1
- YMGJBCGPNTUNSL-UHFFFAOYSA-N methyl 4-(2,4-dichloroanilino)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC=C(Cl)C=C1Cl YMGJBCGPNTUNSL-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US174694A US3228972A (en) | 1962-02-21 | 1962-02-21 | Lower alkyl esters of n-(alkyl) maleamic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH441270A true CH441270A (de) | 1967-08-15 |
Family
ID=22637143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210863A CH441270A (de) | 1962-02-21 | 1963-02-18 | Verfahren zur Herstellung von Amidsäureestern und eine Anwendung derselben |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3228972A (en, 2012) |
| BE (1) | BE628523A (en, 2012) |
| CH (1) | CH441270A (en, 2012) |
| DE (2) | DE1693178A1 (en, 2012) |
| GB (1) | GB1028693A (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3326659A (en) * | 1962-02-21 | 1967-06-20 | Schwartz Herbert | Method for regulating the growth of plants |
| US3375158A (en) * | 1963-11-13 | 1968-03-26 | Gulf Oil Corp | Process for controlling fungi with itaconamic esters |
| US3946074A (en) * | 1970-10-05 | 1976-03-23 | Akzona Incorporated | Plant growth regulatory agents and process |
| US3719467A (en) * | 1971-03-04 | 1973-03-06 | Du Pont | Herbicidal 3-(substituted ureido)crotonamides |
| US4125398A (en) * | 1975-11-07 | 1978-11-14 | Ciba-Geigy Corporation | N-Phenyl-maleic acid amides for regulating the growth and development of plants |
| FR2476075A1 (fr) * | 1980-02-18 | 1981-08-21 | Rhone Poulenc Agrochimie | Nouveaux derives de l'acide methylene-2 succinamique, leur preparation et les compositions regulatrices de la croissance des plantes les contenant |
| DE3204129A1 (de) * | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von ethen- (1,2)-dicarbonamidsaeureestern |
| DE3233830A1 (de) * | 1982-09-11 | 1984-03-15 | Hoechst Ag, 6230 Frankfurt | Perfluoralkyl-malein- und -fumarsaeureamide, verfahren zu deren herstellung und ihre verwendung als schmutzabweisendes mittel |
| US6005062A (en) * | 1998-07-02 | 1999-12-21 | 3M Innovative Properties Company | Secondary aspartic acid amide esters |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2333666A (en) * | 1940-09-14 | 1943-11-09 | American Cyanamid Co | Dialkyl esters of unsaturated dicarboxylic acids as insecticides |
| US2325791A (en) * | 1941-08-30 | 1943-08-03 | American Cyanamid Co | Diamyl maleate as an insecticide |
| US2779704A (en) * | 1951-11-08 | 1957-01-29 | Ethyl Corp | Nu-phenyl maleamic esters |
| US2720452A (en) * | 1952-08-21 | 1955-10-11 | Thompson Boyce Plant Res | Method of treating plants |
| US2768966A (en) * | 1953-01-30 | 1956-10-30 | Int Minerals & Chem Corp | Glutamic acid derivatives and process of producing same |
| US2777872A (en) * | 1953-11-02 | 1957-01-15 | Du Pont | Unsaturated organic compounds |
| US2885319A (en) * | 1953-12-17 | 1959-05-05 | Pittsburgh Coke And Chemical C | N-phenylmaleamic acid esters as fungicides |
| US2913326A (en) * | 1956-01-25 | 1959-11-17 | Stauffer Chemical Co | Propyl-n, n-diethylthiolcarbamate and use as herbicide |
-
0
- BE BE628523D patent/BE628523A/xx unknown
-
1962
- 1962-02-21 US US174694A patent/US3228972A/en not_active Expired - Lifetime
-
1963
- 1963-02-12 GB GB5701/63A patent/GB1028693A/en not_active Expired
- 1963-02-13 DE DE19631693178 patent/DE1693178A1/de active Pending
- 1963-02-13 DE DESCH32779A patent/DE1261511B/de active Pending
- 1963-02-18 CH CH210863A patent/CH441270A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE628523A (en, 2012) | |
| DE1261511B (de) | 1968-02-22 |
| GB1028693A (en) | 1966-05-04 |
| DE1693178A1 (de) | 1969-10-16 |
| US3228972A (en) | 1966-01-11 |
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