HU189528B - Compositions with fungicide activity and process for preparing substituted succinic acid derivatives as active substances thereof - Google Patents
Compositions with fungicide activity and process for preparing substituted succinic acid derivatives as active substances thereof Download PDFInfo
- Publication number
- HU189528B HU189528B HU812384A HU238481A HU189528B HU 189528 B HU189528 B HU 189528B HU 812384 A HU812384 A HU 812384A HU 238481 A HU238481 A HU 238481A HU 189528 B HU189528 B HU 189528B
- Authority
- HU
- Hungary
- Prior art keywords
- succinic acid
- imide
- acid
- formula
- dichlorophenyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 16
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- 150000003443 succinic acid derivatives Chemical class 0.000 title claims description 12
- 230000000694 effects Effects 0.000 title description 4
- 239000000417 fungicide Substances 0.000 title description 4
- 239000013543 active substance Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 polyoxyethylene Polymers 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000001384 succinic acid Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229920001732 Lignosulfonate Polymers 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 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
- 239000000654 additive Substances 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- 230000002528 anti-freeze Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000003949 imides Chemical class 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 13
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 125000005336 allyloxy group Chemical group 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- 235000011044 succinic acid Nutrition 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241000123650 Botrytis cinerea Species 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960002317 succinimide Drugs 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UOUPQZOTGJZSOL-UHFFFAOYSA-N 2-propan-2-yloxybutanedioic acid Chemical compound CC(C)OC(C(O)=O)CC(O)=O UOUPQZOTGJZSOL-UHFFFAOYSA-N 0.000 description 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 4
- 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 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 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
- 238000009835 boiling Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 235000019674 grape juice Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001459558 Monographella nivalis Species 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 241001123663 Penicillium expansum Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004188 dichlorophenyl group Chemical group 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
- 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 3
- 239000002609 medium Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000004563 wettable powder 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- 229920001817 Agar Polymers 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001963 growth medium Substances 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- HPVXTDWZHNAHBN-UHFFFAOYSA-N 2-(2-methylpropoxy)butanedioic acid Chemical compound CC(C)COC(C(O)=O)CC(O)=O HPVXTDWZHNAHBN-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- IDRMDNQYSBDAOJ-UHFFFAOYSA-N 3-ethoxy-4-oxo-4-(propylamino)butanoic acid Chemical compound CCCN=C(O)C(CC(O)=O)OCC IDRMDNQYSBDAOJ-UHFFFAOYSA-N 0.000 description 1
- NTOBCNAVQQSYOV-UHFFFAOYSA-N 4-(butylamino)-3-methoxy-4-oxobutanoic acid Chemical compound CCCCN=C(O)C(OC)CC(O)=O NTOBCNAVQQSYOV-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- QCQVRMIWOFAQDF-UHFFFAOYSA-N CC(CC(O)=O)(C(O)=O)OC(C)=O Chemical compound CC(CC(O)=O)(C(O)=O)OC(C)=O QCQVRMIWOFAQDF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 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
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030926 DE3030926A1 (de) | 1980-08-16 | 1980-08-16 | Substituierte bernsteinsaeureimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189528B true HU189528B (en) | 1986-07-28 |
Family
ID=6109702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU812384A HU189528B (en) | 1980-08-16 | 1981-08-14 | Compositions with fungicide activity and process for preparing substituted succinic acid derivatives as active substances thereof |
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 |
| CA1159460A (en) | 1983-12-27 |
| 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 |
| 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 |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |