CA1159460A - Substituted succinic acid imides and a method for producing the same - Google Patents
Substituted succinic acid imides and a method for producing the sameInfo
- Publication number
- CA1159460A CA1159460A CA000383454A CA383454A CA1159460A CA 1159460 A CA1159460 A CA 1159460A CA 000383454 A CA000383454 A CA 000383454A CA 383454 A CA383454 A CA 383454A CA 1159460 A CA1159460 A CA 1159460A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- radical
- acid
- succinic acid
- imide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 succinic acid imides Chemical class 0.000 title claims abstract description 30
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000001384 succinic acid Substances 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 241000233866 Fungi Species 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 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 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 3
- 229960002317 succinimide Drugs 0.000 claims 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- 239000013543 active substance Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000011044 succinic acid Nutrition 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000126 substance Substances 0.000 description 10
- 230000000855 fungicidal effect Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JRMIGLUYIVIFAU-UHFFFAOYSA-N 2-(methoxymethyl)butanedioic acid Chemical compound COCC(C(O)=O)CC(O)=O JRMIGLUYIVIFAU-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000003443 succinic acid derivatives Chemical class 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- GTWJUDXIBMRDNK-UHFFFAOYSA-N 2-methoxybutanedioic acid Chemical compound COC(C(O)=O)CC(O)=O GTWJUDXIBMRDNK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000722093 Tilletia caries Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 235000019674 grape juice Nutrition 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SSWJHSASZZAIAU-UHFFFAOYSA-N (2,5-dioxooxolan-3-yl) acetate Chemical compound CC(=O)OC1CC(=O)OC1=O SSWJHSASZZAIAU-UHFFFAOYSA-N 0.000 description 2
- CWEMVHMOLPZSHO-UHFFFAOYSA-N 2-(2-methylpropanoyloxy)butanedioic acid Chemical compound CC(C)C(=O)OC(C(O)=O)CC(O)=O CWEMVHMOLPZSHO-UHFFFAOYSA-N 0.000 description 2
- GDXKLPSQGLQURU-UHFFFAOYSA-N 2-ethoxybutanedioic acid Chemical compound CCOC(C(O)=O)CC(O)=O GDXKLPSQGLQURU-UHFFFAOYSA-N 0.000 description 2
- AVTIIDUQKAAYGR-UHFFFAOYSA-N 3-acetyloxy-4-(3,5-dichloroanilino)-4-oxobutanoic acid Chemical compound CC(=O)OC(CC(O)=O)C(O)=NC1=CC(Cl)=CC(Cl)=C1 AVTIIDUQKAAYGR-UHFFFAOYSA-N 0.000 description 2
- IXYFWABPTUIGTD-UHFFFAOYSA-N 3-methoxyoxolane-2,5-dione Chemical compound COC1CC(=O)OC1=O IXYFWABPTUIGTD-UHFFFAOYSA-N 0.000 description 2
- BXYGUPYFAGRRSB-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-3-(methoxymethyl)-4-oxobutanoic acid Chemical compound COCC(CC(O)=O)C(O)=NC1=CC(Cl)=CC(Cl)=C1 BXYGUPYFAGRRSB-UHFFFAOYSA-N 0.000 description 2
- YNZNCTACWNVSDE-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-3-ethoxy-4-oxobutanoic acid Chemical compound CCOC(CC(O)=O)C(O)=NC1=CC(Cl)=CC(Cl)=C1 YNZNCTACWNVSDE-UHFFFAOYSA-N 0.000 description 2
- QXTLZYLYDJBLBG-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-3-methoxy-4-oxobutanoic acid Chemical compound OC(=O)CC(OC)C(O)=NC1=CC(Cl)=CC(Cl)=C1 QXTLZYLYDJBLBG-UHFFFAOYSA-N 0.000 description 2
- LAEFOBSJQMZNSU-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-4-oxo-3-propan-2-yloxybutanoic acid Chemical compound CC(C)OC(CC(O)=O)C(O)=NC1=CC(Cl)=CC(Cl)=C1 LAEFOBSJQMZNSU-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003444 succinic acids Chemical class 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
- UYVRPHIVOKUAPF-UHFFFAOYSA-N 2-acetyloxybutanedioic acid Chemical compound CC(=O)OC(C(O)=O)CC(O)=O UYVRPHIVOKUAPF-UHFFFAOYSA-N 0.000 description 1
- HDRVDLVRHXIHKD-UHFFFAOYSA-N 2-cyclohex-2-en-1-ylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)C1CCCC=C1 HDRVDLVRHXIHKD-UHFFFAOYSA-N 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- JSOITVUXVSRGHC-UHFFFAOYSA-N 3-acetyloxy-4-(3-chloroanilino)-4-oxobutanoic acid Chemical compound CC(=O)OC(CC(O)=O)C(O)=NC1=CC=CC(Cl)=C1 JSOITVUXVSRGHC-UHFFFAOYSA-N 0.000 description 1
- PARNFRCLFLEWOR-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-4-oxo-3-propoxybutanoic acid Chemical compound CCCOC(CC(O)=O)C(O)=NC1=CC(Cl)=CC(Cl)=C1 PARNFRCLFLEWOR-UHFFFAOYSA-N 0.000 description 1
- OHGHIFSSYCPDIV-UHFFFAOYSA-N 4-(butan-2-ylamino)-3-(methoxymethyl)-4-oxobutanoic acid Chemical compound CCC(C)N=C(O)C(COC)CC(O)=O OHGHIFSSYCPDIV-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000612152 Cyclamen hederifolium Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241000208150 Geraniaceae Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241001123663 Penicillium expansum Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241001123668 Verticillium dahliae Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical class CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229930186364 cyclamen Natural products 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HYPQWVMAJDZMLL-UHFFFAOYSA-N dimethyl 2-(methoxymethyl)butanedioate Chemical compound COCC(C(=O)OC)CC(=O)OC HYPQWVMAJDZMLL-UHFFFAOYSA-N 0.000 description 1
- CZGCYHISZCRQFR-UHFFFAOYSA-N dimethyl 2-methoxybutanedioate Chemical compound COC(=O)C(OC)CC(=O)OC CZGCYHISZCRQFR-UHFFFAOYSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
-
- 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
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030926 DE3030926A1 (de) | 1980-08-16 | 1980-08-16 | Substituierte bernsteinsaeureimide |
| DEP3030926.3 | 1980-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159460A true CA1159460A (en) | 1983-12-27 |
Family
ID=6109702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000383454A Expired CA1159460A (en) | 1980-08-16 | 1981-08-07 | Substituted succinic acid imides and a method for producing the same |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4460782A (en, 2012) |
| EP (1) | EP0046274B1 (en, 2012) |
| JP (1) | JPS6019901B2 (en, 2012) |
| AR (1) | AR229097A1 (en, 2012) |
| AT (1) | ATE8882T1 (en, 2012) |
| AU (1) | AU545736B2 (en, 2012) |
| BR (1) | BR8105177A (en, 2012) |
| CA (1) | CA1159460A (en, 2012) |
| DE (2) | DE3030926A1 (en, 2012) |
| ES (1) | ES8206469A1 (en, 2012) |
| GR (1) | GR74629B (en, 2012) |
| HU (1) | HU189528B (en, 2012) |
| IL (1) | IL62935A (en, 2012) |
| PT (1) | PT72946B (en, 2012) |
| ZA (1) | ZA815405B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030926A1 (de) * | 1980-08-16 | 1982-04-01 | Consortium für elektrochemische Industrie GmbH, 8000 München | Substituierte bernsteinsaeureimide |
| IL76200A0 (en) * | 1984-08-30 | 1985-12-31 | Consortium Elektrochem Ind | Substituted 1-phenyl-3-methyl-pyrrolidinediones,their preparation and their use as fungicides |
| EP0223328B1 (en) * | 1985-07-26 | 1992-01-29 | Denki Kagaku Kogyo Kabushiki Kaisha | Process for producing oxiracetam |
| US4678826A (en) * | 1986-01-24 | 1987-07-07 | Ciba-Geigy Corporation | Substituted-(aminoxy)-pyrrolidine-2,5-dione stabilizers |
| AU9318498A (en) * | 1997-09-18 | 1999-04-05 | Pierce Chemical Company | Sulfo-n-hydroxy succinimide and method of preparation |
| US5892057A (en) | 1997-09-18 | 1999-04-06 | Pierce Chemical Company | Preparation of sulfo-N-hydroxysuccinimide salts |
| AU2015246991A1 (en) * | 2014-04-16 | 2016-11-24 | Nihon Nohyaku Co., Ltd. | Method for Controlling Plant Diseases |
| RU2668548C1 (ru) * | 2018-08-02 | 2018-10-02 | Федеральное государственное бюджетное учреждение науки Институт проблем химико-энергетических технологий Сибирского отделения Российской академии наук (ИПХЭТ СО РАН) | Способ получения этоксиянтарной кислоты |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184475A (en) * | 1961-09-15 | 1965-05-18 | Monsanto Co | Maleimides, maleamides and fumaramides |
| US3586697A (en) * | 1967-12-01 | 1971-06-22 | Sumitomo Chemical Co | Novel n-(3,5-dichlorophenyl) cyclic imide derivatives |
| FR2015493A1 (en, 2012) * | 1968-08-12 | 1970-04-30 | Sumitomo Chemical Co | |
| US3745170A (en) * | 1969-03-19 | 1973-07-10 | Sumitomo Chemical Co | Novel n-(3,5-dihalophenyl)-imide compounds |
| US3804856A (en) * | 1970-09-04 | 1974-04-16 | Sumitomo Chemical Co | N-phenylsuccinimides |
| US3816451A (en) * | 1971-11-02 | 1974-06-11 | Abbott Lab | Maleimide derivatives as plant growth regulators |
| JPS527956A (en) * | 1975-07-09 | 1977-01-21 | Nippon Soda Co Ltd | Succinimide derivatives and its preparation |
| JPS5212161A (en) * | 1975-07-18 | 1977-01-29 | Nippon Soda Co Ltd | Succinimide compounds and fungicides for agricultural and gardening us e |
| JPS5243886A (en) * | 1975-10-06 | 1977-04-06 | Mitsubishi Paper Mills Ltd | Process for manufacturing composite board |
| US4076110A (en) * | 1976-09-13 | 1978-02-28 | Eaton Corporation | Quick disengagement viscous drive coupling |
| DE2740848A1 (de) * | 1977-09-10 | 1979-03-29 | Bayer Ag | Substituierte n-phenyl-bernsteinsaeureimide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE3030926A1 (de) * | 1980-08-16 | 1982-04-01 | Consortium für elektrochemische Industrie GmbH, 8000 München | Substituierte bernsteinsaeureimide |
-
1980
- 1980-08-16 DE DE19803030926 patent/DE3030926A1/de not_active Withdrawn
-
1981
- 1981-04-29 PT PT72946A patent/PT72946B/pt not_active IP Right Cessation
- 1981-05-21 JP JP56077331A patent/JPS6019901B2/ja not_active Expired
- 1981-05-21 GR GR65018A patent/GR74629B/el unknown
- 1981-05-22 IL IL62935A patent/IL62935A/xx unknown
- 1981-07-22 AR AR286166A patent/AR229097A1/es active
- 1981-07-24 US US06/286,569 patent/US4460782A/en not_active Expired - Fee Related
- 1981-08-06 ZA ZA815405A patent/ZA815405B/xx unknown
- 1981-08-07 CA CA000383454A patent/CA1159460A/en not_active Expired
- 1981-08-07 AU AU73874/81A patent/AU545736B2/en not_active Ceased
- 1981-08-12 BR BR8105177A patent/BR8105177A/pt unknown
- 1981-08-13 DE DE8181106296T patent/DE3165401D1/de not_active Expired
- 1981-08-13 AT AT81106296T patent/ATE8882T1/de not_active IP Right Cessation
- 1981-08-13 EP EP81106296A patent/EP0046274B1/de not_active Expired
- 1981-08-14 HU HU812384A patent/HU189528B/hu not_active IP Right Cessation
- 1981-08-14 ES ES504753A patent/ES8206469A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU7387481A (en) | 1982-02-25 |
| ATE8882T1 (de) | 1984-08-15 |
| GR74629B (en, 2012) | 1984-06-29 |
| EP0046274A1 (de) | 1982-02-24 |
| DE3030926A1 (de) | 1982-04-01 |
| ZA815405B (en) | 1982-08-25 |
| PT72946A (en) | 1981-05-01 |
| DE3165401D1 (en) | 1984-09-13 |
| JPS5742668A (en) | 1982-03-10 |
| IL62935A0 (en) | 1981-07-31 |
| US4460782A (en) | 1984-07-17 |
| AR229097A1 (es) | 1983-06-15 |
| ES504753A0 (es) | 1982-08-16 |
| JPS6019901B2 (ja) | 1985-05-18 |
| HU189528B (en) | 1986-07-28 |
| IL62935A (en) | 1984-05-31 |
| BR8105177A (pt) | 1982-04-27 |
| EP0046274B1 (de) | 1984-08-08 |
| AU545736B2 (en) | 1985-08-01 |
| ES8206469A1 (es) | 1982-08-16 |
| PT72946B (en) | 1982-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20001227 |