FI70210C - Nya som herbicider anvaendbara n-acyl-pyrrol-2,5-dion-derivat och deras framstaellning - Google Patents
Nya som herbicider anvaendbara n-acyl-pyrrol-2,5-dion-derivat och deras framstaellning Download PDFInfo
- Publication number
- FI70210C FI70210C FI782316A FI782316A FI70210C FI 70210 C FI70210 C FI 70210C FI 782316 A FI782316 A FI 782316A FI 782316 A FI782316 A FI 782316A FI 70210 C FI70210 C FI 70210C
- Authority
- FI
- Finland
- Prior art keywords
- phenylamino
- carbethoxymaleimide
- alkyl
- chloro
- phenyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 benzylthio Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 150000003949 imides Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- YZXWPSHBVRQJTQ-UHFFFAOYSA-N ethyl 3-(4-chloroanilino)-2,5-dioxopyrrolidine-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)CC1NC1=CC=C(Cl)C=C1 YZXWPSHBVRQJTQ-UHFFFAOYSA-N 0.000 claims description 2
- HCUWCRFXCLLXIQ-UHFFFAOYSA-N ethyl 3-(4-methylanilino)-2,5-dioxopyrrolidine-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)CC1NC1=CC=C(C)C=C1 HCUWCRFXCLLXIQ-UHFFFAOYSA-N 0.000 claims description 2
- IRHCZZGNZLDDPI-UHFFFAOYSA-N ethyl 3-(benzenesulfonyl)-2,5-dioxopyrrole-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)C=C1S(=O)(=O)C1=CC=CC=C1 IRHCZZGNZLDDPI-UHFFFAOYSA-N 0.000 claims description 2
- WTNNABYHLDFSCM-UHFFFAOYSA-N ethyl 3-(cyclohexylamino)-2,5-dioxopyrrole-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)C=C1NC1CCCCC1 WTNNABYHLDFSCM-UHFFFAOYSA-N 0.000 claims description 2
- PLYTYJLQHJLLAC-UHFFFAOYSA-N ethyl 3-(hexylamino)-2,5-dioxopyrrole-1-carboxylate Chemical compound CCCCCCNC1=CC(=O)N(C(=O)OCC)C1=O PLYTYJLQHJLLAC-UHFFFAOYSA-N 0.000 claims description 2
- KUQPDYOPSWJURR-UHFFFAOYSA-N ethyl 3-[2-(3,4-dimethoxyphenyl)ethylamino]-2,5-dioxopyrrole-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)C=C1NCCC1=CC=C(OC)C(OC)=C1 KUQPDYOPSWJURR-UHFFFAOYSA-N 0.000 claims description 2
- REQRFUUFSYGFTO-UHFFFAOYSA-N ethyl 3-anilino-2,5-dioxopyrrole-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)C=C1NC1=CC=CC=C1 REQRFUUFSYGFTO-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 4
- CFHMRJUTHATPLW-UHFFFAOYSA-N 3-anilinopyrrole-2,5-dione Chemical compound O=C1NC(=O)C(NC=2C=CC=CC=2)=C1 CFHMRJUTHATPLW-UHFFFAOYSA-N 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229960002317 succinimide Drugs 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 240000002234 Allium sativum Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000004611 garlic Nutrition 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- VRIBRNJSGPJXJI-UHFFFAOYSA-N 1-acetyl-3-anilinopyrrole-2,5-dione Chemical compound O=C1N(C(=O)C)C(=O)C=C1NC1=CC=CC=C1 VRIBRNJSGPJXJI-UHFFFAOYSA-N 0.000 description 1
- RHLBOBPOIZROJX-UHFFFAOYSA-N 1-acetylpyrrolidine-2,5-dione Chemical compound CC(=O)N1C(=O)CCC1=O RHLBOBPOIZROJX-UHFFFAOYSA-N 0.000 description 1
- CLFHABXQJQAYEF-UHFFFAOYSA-N 1-benzoylpyrrolidine-2,5-dione Chemical compound C=1C=CC=CC=1C(=O)N1C(=O)CCC1=O CLFHABXQJQAYEF-UHFFFAOYSA-N 0.000 description 1
- OMYOJDLCFAUIHN-UHFFFAOYSA-N 1-pyrrol-1-ylethanone Chemical compound CC(=O)N1C=CC=C1 OMYOJDLCFAUIHN-UHFFFAOYSA-N 0.000 description 1
- SRJJPZOPXHUCBS-UHFFFAOYSA-N 3-anilino-1-benzoylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C(=O)N(C1=O)C(=O)C=C1NC1=CC=CC=C1 SRJJPZOPXHUCBS-UHFFFAOYSA-N 0.000 description 1
- UDESUGJZUFALAM-UHFFFAOYSA-N 3-methyl-3-phenylpyrrolidine-2,5-dione Chemical compound C=1C=CC=CC=1C1(C)CC(=O)NC1=O UDESUGJZUFALAM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 229910017489 Cu I Inorganic materials 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000002756 Erythrina berteroana Nutrition 0.000 description 1
- 244000088811 Erythrina rubrinervia Species 0.000 description 1
- 235000002753 Erythrina rubrinervia Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- 125000000773 L-serino group Chemical group [H]OC(=O)[C@@]([H])(N([H])*)C([H])([H])O[H] 0.000 description 1
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
- 241001275117 Seres Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- HACODILRQLESNH-UHFFFAOYSA-N ethyl 2,5-dioxopyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1C(=O)CCC1=O HACODILRQLESNH-UHFFFAOYSA-N 0.000 description 1
- HDOMPHRXTWLAQP-UHFFFAOYSA-N ethyl 3-anilino-2,5-dioxopyrrolidine-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)CC1NC1=CC=CC=C1 HDOMPHRXTWLAQP-UHFFFAOYSA-N 0.000 description 1
- OGKRSONONAVGND-UHFFFAOYSA-N ethyl 3-methyl-2,5-dioxo-3-phenylpyrrolidine-1-carboxylate Chemical compound O=C1N(C(=O)OCC)C(=O)CC1(C)C1=CC=CC=C1 OGKRSONONAVGND-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical class NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure 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
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
-
- 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
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- 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
-
- 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
- C07D207/44—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 three double bonds between ring members or between ring members and non-ring members
- C07D207/444—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 three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/456—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 three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 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
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1757A HU175454B (hu) | 1977-07-25 | 1977-07-25 | Sposob poluchenija novykh predel'nykh i chastichno predel'nykh n-acil-pirrol-2,5-dionov |
| HUCI001757 | 1977-07-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782316A7 FI782316A7 (fi) | 1979-01-26 |
| FI70210B FI70210B (fi) | 1986-02-28 |
| FI70210C true FI70210C (fi) | 1986-09-15 |
Family
ID=10994661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782316A FI70210C (fi) | 1977-07-25 | 1978-07-24 | Nya som herbicider anvaendbara n-acyl-pyrrol-2,5-dion-derivat och deras framstaellning |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4353734A (cs) |
| JP (1) | JPS54112857A (cs) |
| AT (1) | AT371110B (cs) |
| BE (1) | BE869236A (cs) |
| CH (1) | CH642352A5 (cs) |
| CS (1) | CS208480B2 (cs) |
| DD (1) | DD141020A5 (cs) |
| DE (1) | DE2831654A1 (cs) |
| ES (1) | ES471976A1 (cs) |
| FI (1) | FI70210C (cs) |
| FR (1) | FR2398731A1 (cs) |
| GB (1) | GB2003857B (cs) |
| HU (1) | HU175454B (cs) |
| IT (1) | IT1192621B (cs) |
| NL (1) | NL7807875A (cs) |
| PL (1) | PL111203B1 (cs) |
| SU (1) | SU1282814A3 (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9408994D0 (en) * | 1994-05-06 | 1994-06-22 | Vanguard Medica Ltd | Compounds |
| TW442467B (en) * | 1996-06-10 | 2001-06-23 | American Cyanamid Co | Process for the preparation of 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds |
| US5905154A (en) * | 1996-06-10 | 1999-05-18 | American Cyanamid Company | Process for the preparation of 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds |
| US6719520B2 (en) * | 1998-10-08 | 2004-04-13 | Smithkline Beecham Corporation | Method and compounds |
| US7704552B2 (en) * | 1999-08-19 | 2010-04-27 | Ppg Industries Ohio, Inc. | Process for producing chemically treated amorphous precipitated silica |
| JP4029960B2 (ja) * | 2001-10-05 | 2008-01-09 | 独立行政法人理化学研究所 | アブシジン酸生合成阻害剤 |
| SG173922A1 (en) | 2002-11-27 | 2011-09-29 | Incyte Corp | 3-aminopyrrolidine derivatives as modulators of chemokine receptors |
| OA13338A (en) * | 2003-12-18 | 2007-04-13 | Incyte Corp | 3-cycloalkylaminopyrrolidine derivates as modulators of chemokine receptors. |
| NZ550511A (en) * | 2004-05-11 | 2010-07-30 | Incyte Corp | 3-(4-Heteroarylcyclohexylamino)cyclopentanecarboxamides as modulators of chemokine receptors |
| EA012601B1 (ru) * | 2004-05-12 | 2009-10-30 | Байер Кропсайенс Аг | Регулирование роста растений |
| PA8653301A1 (es) * | 2004-11-22 | 2006-11-09 | Incyte Corp Incyte Corp | Sales de la n-[2-({(3r)-1-[trans-4-hidroxi-4-(6-metoxipiridin-3-il) ciclohexil)pirrolidin |
| GB0520368D0 (en) * | 2005-10-06 | 2005-11-16 | Univ Aston | Antibacterial pyrrols |
| FR2905695B1 (fr) | 2006-09-13 | 2008-10-24 | Saint Gobain Isover Sa | Compositions pour laines minerales |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3882145A (en) * | 1972-12-22 | 1975-05-06 | Ppg Industries Inc | Halogenated N-substituted thiocarboxy maleimides |
| DE2352448A1 (de) * | 1973-10-19 | 1975-04-30 | Hoechst Ag | Magnesidin und verfahren zu seiner herstellung |
| JPS51125104A (en) * | 1974-10-21 | 1976-11-01 | Hitachi Chem Co Ltd | Resinous coating compositions |
-
1977
- 1977-07-25 HU HU77CI1757A patent/HU175454B/hu unknown
-
1978
- 1978-07-19 DE DE19782831654 patent/DE2831654A1/de not_active Ceased
- 1978-07-22 ES ES471976A patent/ES471976A1/es not_active Expired
- 1978-07-24 PL PL1978208616A patent/PL111203B1/pl unknown
- 1978-07-24 FI FI782316A patent/FI70210C/fi not_active IP Right Cessation
- 1978-07-24 FR FR7821833A patent/FR2398731A1/fr active Granted
- 1978-07-24 DD DD78206893A patent/DD141020A5/de unknown
- 1978-07-24 CH CH797178A patent/CH642352A5/de not_active IP Right Cessation
- 1978-07-24 IT IT68754/78A patent/IT1192621B/it active
- 1978-07-24 CS CS784918A patent/CS208480B2/cs unknown
- 1978-07-24 SU SU782640407A patent/SU1282814A3/ru active
- 1978-07-24 US US05/927,343 patent/US4353734A/en not_active Expired - Lifetime
- 1978-07-25 JP JP9086578A patent/JPS54112857A/ja active Pending
- 1978-07-25 BE BE189472A patent/BE869236A/xx not_active IP Right Cessation
- 1978-07-25 AT AT0539278A patent/AT371110B/de not_active IP Right Cessation
- 1978-07-25 GB GB7831053A patent/GB2003857B/en not_active Expired
- 1978-07-25 NL NL7807875A patent/NL7807875A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BE869236A (fr) | 1978-11-16 |
| PL208616A1 (pl) | 1979-05-07 |
| ES471976A1 (es) | 1979-12-16 |
| CS208480B2 (en) | 1981-09-15 |
| FR2398731A1 (fr) | 1979-02-23 |
| IT1192621B (it) | 1988-04-27 |
| US4353734A (en) | 1982-10-12 |
| PL111203B1 (en) | 1980-08-30 |
| FR2398731B3 (cs) | 1980-10-24 |
| NL7807875A (nl) | 1979-01-29 |
| ATA539278A (de) | 1982-10-15 |
| FI782316A7 (fi) | 1979-01-26 |
| FI70210B (fi) | 1986-02-28 |
| JPS54112857A (en) | 1979-09-04 |
| GB2003857B (en) | 1982-01-27 |
| CH642352A5 (de) | 1984-04-13 |
| DE2831654A1 (de) | 1979-02-15 |
| AT371110B (de) | 1983-06-10 |
| DD141020A5 (de) | 1980-04-09 |
| GB2003857A (en) | 1979-03-21 |
| IT7868754A0 (it) | 1978-07-24 |
| HU175454B (hu) | 1980-08-28 |
| SU1282814A3 (ru) | 1987-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI70210C (fi) | Nya som herbicider anvaendbara n-acyl-pyrrol-2,5-dion-derivat och deras framstaellning | |
| BR9905766B1 (pt) | derivado de ftalamida, insetidida agro-hortìcula, e, processo para a utilização do mesmo. | |
| GB2071100A (en) | Herbicidal n-substituted - '-tetrahydrophthalimide derivatives | |
| PT712853E (pt) | Derivado de pirazol | |
| RU2045512C1 (ru) | 2-[ 2′,3′,4′ -тризамещенные бензоил]-1,3-циклогександионы или их соли, гербицидная композиция и способ борьбы с нежелательной растительностью | |
| SU1748628A3 (ru) | Акарицидна композици | |
| CS212332B2 (en) | Fungicide means | |
| JPH04316559A (ja) | ピラゾールカルボキサニリド誘導体及び殺菌剤 | |
| HU185801B (en) | Process for preparing new benzamide derivatives and herbicide compositions containing benzamide derivatives as active suastances | |
| JPS63258467A (ja) | ２−フエノキシトリアジン誘導体及び除草剤 | |
| US4210440A (en) | Urea derivatives, process for preparing the same and herbicidal composition containing the same | |
| JPS60109578A (ja) | ３−（置換フエニル）−５−置換−１，３，４−オキサゾリン−２−オン類およびこれを有効成分とする除草剤 | |
| US5068365A (en) | Hexahydrophthalic anilide derivatives | |
| JPS62169785A (ja) | ナフチリジン−誘導体、その製法及びこれを含有する除草剤 | |
| EP0073409B1 (en) | N-substituted-tetrahydroisophthalimide derivatives | |
| EP0476573B1 (en) | 2-tButyl-4-chloro-5-(4-ibutylmethylcyclohexyl)-methylthio-3(H)-pyridazinone having acaricidal and insecticidal activity | |
| JP2650824B2 (ja) | Ｎ−アシル−ｎ−フェニルマレアミド酸誘導体およびその製造法ならびにそれを有効成分とする除草剤 | |
| US4284626A (en) | O-aryl S-branched alkyl alkylphosphonodithioate insecticides and nematocides | |
| CN119528885A (zh) | 一种含吡咯-2,5-二酮结构的5-酰基巴比妥酸类化合物和制备方法及其除草剂应用 | |
| HUP0100134A2 (hu) | 1-Metil-5-(alkil-szulfonil/szulfinil vagy tio)-csoporttal szubsztituált pirazolil-pirazol-származékok, előállításuk és alkalmazásuk herbicidként | |
| US4282028A (en) | Herbicidal and plant-growth-regulating N-substituted-N-(2,5-dialkylpyrrol-1-yl) haloacetamides | |
| KR0120271B1 (ko) | α-카르보닐이미노 구조를 갖는 신규 제초성 피리미딘 유도체, 그의 제조방법 및 그를 함유하는 제초제 조성물 | |
| JP2003012625A (ja) | アミド誘導体および農薬 | |
| KR950011417B1 (ko) | 신규 2-페녹시피리미딘 유도체 및 그의 제조방법 | |
| JPH01113388A (ja) | 除草剤組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |