CS208480B2 - Method of making the new derivatives of the maleinimide or sucinimide - Google Patents

Method of making the new derivatives of the maleinimide or sucinimide Download PDF

Info

Publication number: CS208480B2
Authority: CS; Czechoslovakia
Prior art keywords: alkyl; formula; hydrogen; phenyl; substituted
Prior art date: 1977-07-25

Application number

CS784918A

Other languages

Czech (cs)

English (en)

Inventor

Jenoe Seres

Istvanne Daroczi

Janosne Varkonyi

Gabor Horvath

Ildiko Szilahyi

Belene Radvany

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date 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 date listed.)

1977-07-25

Filing date

1978-07-24

Publication date

1981-09-15

1978-07-24 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1981-09-15 Publication of CS208480B2 publication Critical patent/CS208480B2/cs

Links

238000004519 manufacturing process Methods 0.000 title claims 2
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 31
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
239000011230 binding agent Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000008065 acid anhydrides Chemical group 0.000 claims description 4
229960002317 succinimide Drugs 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 19
238000002360 preparation method Methods 0.000 abstract description 8
230000002363 herbicidal effect Effects 0.000 abstract description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
229940053198 antiepileptics succinimide derivative Drugs 0.000 abstract description 3
230000010933 acylation Effects 0.000 abstract description 2
238000005917 acylation reaction Methods 0.000 abstract description 2
239000004009 herbicide Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
239000000126 substance Substances 0.000 abstract description 2
-1 phenylthio, phenoxy, phenoxy Chemical class 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
229910052801 chlorine Inorganic materials 0.000 description 12
238000003756 stirring Methods 0.000 description 10
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
239000011541 reaction mixture Substances 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000035784 germination Effects 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
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 3
241000219198 Brassica Species 0.000 description 3
235000003351 Brassica cretica Nutrition 0.000 description 3
235000003343 Brassica rupestris Nutrition 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
235000010460 mustard Nutrition 0.000 description 3
QBLRHWLVSHLMSP-UHFFFAOYSA-N 3-bromopyrrole-2,5-dione Chemical compound BrC1=CC(=O)NC1=O QBLRHWLVSHLMSP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
241000196324 Embryophyta Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000232088 Setaria <nematode> Species 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 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
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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
MVCMCMDKJCCYFQ-UHFFFAOYSA-N Cl.ClCC(Cl)(Cl)Cl Chemical compound Cl.ClCC(Cl)(Cl)Cl MVCMCMDKJCCYFQ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
235000005775 Setaria 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
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
239000002318 adhesion promoter Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
101150047356 dec-1 gene Proteins 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
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 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration 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
125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000002563 ionic surfactant Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NNLJLPZWDPOEAW-UHFFFAOYSA-N potassium;pyrrolidine-2,5-dione Chemical compound [K].O=C1CCC(=O)N1 NNLJLPZWDPOEAW-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000007017 scission Effects 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
239000002689 soil Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005406 washing 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)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

CS784918A 1977-07-25 1978-07-24 Method of making the new derivatives of the maleinimide or sucinimide CS208480B2 (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CS208480B2 true CS208480B2 (en)	1981-09-15

Family

ID=10994661

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS784918A CS208480B2 (en)	1977-07-25	1978-07-24	Method of making the new derivatives of the maleinimide or sucinimide

Country Status (17)

Country	Link
US (1)	US4353734A (pl)
JP (1)	JPS54112857A (pl)
AT (1)	AT371110B (pl)
BE (1)	BE869236A (pl)
CH (1)	CH642352A5 (pl)
CS (1)	CS208480B2 (pl)
DD (1)	DD141020A5 (pl)
DE (1)	DE2831654A1 (pl)
ES (1)	ES471976A1 (pl)
FI (1)	FI70210C (pl)
FR (1)	FR2398731A1 (pl)
GB (1)	GB2003857B (pl)
HU (1)	HU175454B (pl)
IT (1)	IT1192621B (pl)
NL (1)	NL7807875A (pl)
PL (1)	PL111203B1 (pl)
SU (1)	SU1282814A3 (pl)

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GB9408994D0 (en) *	1994-05-06	1994-06-22	Vanguard Medica Ltd	Compounds
US5905154A (en) *	1996-06-10	1999-05-18	American Cyanamid Company	Process for the preparation of 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds
TW442467B (en) *	1996-06-10	2001-06-23	American Cyanamid Co	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
GEP20115290B (en)	2002-11-27	2011-09-26	Incyte Corp	3-aminopyrrolidine derivatives as modulators of chemokine receptors
UA82917C2 (en) *	2003-12-18	2008-05-26		3-cycloalkylaminopyrrolidine derivatives as modulators of chemokine receptor
KR100837019B1 (ko) *	2004-05-11	2008-06-10	인사이트 코포레이션	케모카인 수용체 조절제로서3-(4-헤테로아릴사이클로헥실아미노)사이클로펜탄카복스아마이드
CN1949967B (zh) *	2004-05-12	2012-02-01	拜尔作物科学有限公司	植物生长调节作用
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

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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 DD DD78206893A patent/DD141020A5/de unknown
- 1978-07-24 IT IT68754/78A patent/IT1192621B/it active
- 1978-07-24 FR FR7821833A patent/FR2398731A1/fr active Granted
- 1978-07-24 CS CS784918A patent/CS208480B2/cs unknown
- 1978-07-24 PL PL1978208616A patent/PL111203B1/pl unknown
- 1978-07-24 US US05/927,343 patent/US4353734A/en not_active Expired - Lifetime
- 1978-07-24 CH CH797178A patent/CH642352A5/de not_active IP Right Cessation
- 1978-07-24 SU SU782640407A patent/SU1282814A3/ru active
- 1978-07-24 FI FI782316A patent/FI70210C/fi not_active IP Right Cessation
- 1978-07-25 NL NL7807875A patent/NL7807875A/xx not_active Application Discontinuation
- 1978-07-25 BE BE189472A patent/BE869236A/xx not_active IP Right Cessation
- 1978-07-25 JP JP9086578A patent/JPS54112857A/ja active Pending
- 1978-07-25 GB GB7831053A patent/GB2003857B/en not_active Expired
- 1978-07-25 AT AT0539278A patent/AT371110B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI782316A7 (fi)	1979-01-26
NL7807875A (nl)	1979-01-29
BE869236A (fr)	1978-11-16
IT7868754A0 (it)	1978-07-24
FI70210C (fi)	1986-09-15
PL111203B1 (en)	1980-08-30
SU1282814A3 (ru)	1987-01-07
DE2831654A1 (de)	1979-02-15
US4353734A (en)	1982-10-12
FI70210B (fi)	1986-02-28
FR2398731A1 (fr)	1979-02-23
GB2003857A (en)	1979-03-21
JPS54112857A (en)	1979-09-04
ES471976A1 (es)	1979-12-16
DD141020A5 (de)	1980-04-09
AT371110B (de)	1983-06-10
PL208616A1 (pl)	1979-05-07
HU175454B (hu)	1980-08-28
CH642352A5 (de)	1984-04-13
IT1192621B (it)	1988-04-27
GB2003857B (en)	1982-01-27
ATA539278A (de)	1982-10-15
FR2398731B3 (pl)	1980-10-24

Publication	Publication Date	Title
CS208480B2 (en)	1981-09-15	Method of making the new derivatives of the maleinimide or sucinimide
JPS62258344A (ja)	1987-11-10	アクリル酸誘導体、その製造法及びそれを含有する殺菌剤組成物
JPWO1995004054A1 (ja)	1995-10-05	ピラゾール誘導体
BG60602B1 (bg)	1995-10-31	Хербицидно средство и метод за борба с плевели
US4885023A (en)	1989-12-05	Thiadiazabicyclononane derivatives and herbicidal compositions
HU203334B (en)	1991-07-29	Process for producing urea derivatives and herbicide compositions containing them as active components
US4091037A (en)	1978-05-23	Preparation of alkylthiomethylphenols
NL193833C (nl)	2000-12-04	5-Amino-3-oxo-4(gesubstitueerd fenyl)-2,3-dihydrofuranverbindingen met herbicide werking en herbicide preparaat dat deze verbindingen bevat.
JPH0797349A (ja)	1995-04-11	ジフェニルエーテル誘導体およびその製造方法
CZ261997A3 (en)	1997-12-17	Triazine derivatives
JPH0753718B2 (ja)	1995-06-07	Ｎ‐置換‐３‐（置換ヒドラジノ）ベンゼンスルホンアミド誘導体、その製造方法及び除草剤
DE69408950T2 (de)	1998-10-15	N-Pyrazolylcarbamatderivate und Fungizide für Landwirtschaft und Gartenbau, die diese als aktive Bestandteile erhalten, Produktion und Zwischenprodukte
SU1584737A3 (ru)	1990-08-07	Способ борьбы с сорн ками
EP0041256A1 (en)	1981-12-09	Hexahydroisoindol derivatives, process for producing said compounds and herbicides containing said compounds
JP3041957B2 (ja)	2000-05-15	Ｎ−フェニルテトラヒドロフタラミン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
US4185994A (en)	1980-01-29	Herbicidal compound
US4948905A (en)	1990-08-14	Synthesis of vinyl lactones
NZ228087A (en)	1991-05-28	Imidazolinone derivatives; pharmaceutical compositions and preparatory processes
SU591145A3 (ru)	1978-01-30	Способ получени производных 2,4-диметил-3-карбоксианилидфурана или их солей
Herrera et al.	2003	The reaction of thioesters with nitriles. A new synthetic approach to the preparation of substituted 4-alkylthio-and 4-arylthiopyrimidine derivatives
EP0476761A1 (en)	1992-03-25	4-substituted isoxazoles
JPH04149173A (ja)	1992-05-22	マレイミド化合物、その製造方法、および抗菌剤組成物
US4282028A (en)	1981-08-04	Herbicidal and plant-growth-regulating N-substituted-N-(2,5-dialkylpyrrol-1-yl) haloacetamides
US5114466A (en)	1992-05-19	1-(3-substituted benzyl)-3-halogeno-4-(1-halogeno-alkyl)-2-pyrrolidinone derivatives and herbicides containing them
GB1591374A (en)	1981-06-24	Heterocyclic hydroxy ketones and their use as herbicides