DE3544850A1 - Pyron-3-carboxamidverbindungen - Google Patents
Pyron-3-carboxamidverbindungenInfo
- Publication number
- DE3544850A1 DE3544850A1 DE19853544850 DE3544850A DE3544850A1 DE 3544850 A1 DE3544850 A1 DE 3544850A1 DE 19853544850 DE19853544850 DE 19853544850 DE 3544850 A DE3544850 A DE 3544850A DE 3544850 A1 DE3544850 A1 DE 3544850A1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- carboxamide
- pyran
- dimethyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RGJHJUZHUCDDAC-UHFFFAOYSA-N 2,6-dimethyl-4-oxopyran-3-carboxamide Chemical class CC1=CC(=O)C(C(N)=O)=C(C)O1 RGJHJUZHUCDDAC-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 230000009036 growth inhibition Effects 0.000 description 4
- -1 halogen derivatives of 2 , 6-Dimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 235000019057 Raphanus caudatus Nutrition 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000011380 Raphanus sativus Nutrition 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UHANVDZCDNSILX-UHFFFAOYSA-N n-phenylbutanamide Chemical class CCCC(=O)NC1=CC=CC=C1 UHANVDZCDNSILX-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RKWCRGHPMNSTCV-QXMHVHEDSA-N (z)-3-morpholin-4-yl-n-phenylbut-2-enamide Chemical class C1COCCN1C(/C)=C\C(=O)NC1=CC=CC=C1 RKWCRGHPMNSTCV-QXMHVHEDSA-N 0.000 description 1
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- URHWMZVMAAUENN-UHFFFAOYSA-N 1,3-dioxin-4-one Chemical compound O=C1OCOC=C1 URHWMZVMAAUENN-UHFFFAOYSA-N 0.000 description 1
- AUGDHDJZMNDHTE-UHFFFAOYSA-N 2,6-dimethyl-4-oxo-n-phenylpyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C=CC=CC=2)=C1C AUGDHDJZMNDHTE-UHFFFAOYSA-N 0.000 description 1
- MZMRFDKQPOMOGX-UHFFFAOYSA-N 2,6-dimethyl-4-oxopyran-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=C(C)O1 MZMRFDKQPOMOGX-UHFFFAOYSA-N 0.000 description 1
- UDDMNUVPYLZNBC-UHFFFAOYSA-N 2,6-dimethyl-n-(2-nitrophenyl)-4-oxopyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C(=CC=CC=2)[N+]([O-])=O)=C1C UDDMNUVPYLZNBC-UHFFFAOYSA-N 0.000 description 1
- DYIBXAZAMLTKLE-UHFFFAOYSA-N 2,6-dimethyl-n-(4-methylphenyl)-4-oxopyran-3-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=C(C)OC(C)=CC1=O DYIBXAZAMLTKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- PJOMFEHOLJKQAZ-UHFFFAOYSA-N 4-oxopyran-3-carboxylic acid Chemical compound OC(=O)C1=COC=CC1=O PJOMFEHOLJKQAZ-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 101000909811 Homo sapiens Protein cornichon homolog 2 Proteins 0.000 description 1
- 240000005783 Lathyrus sativus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102100024446 Protein cornichon homolog 2 Human genes 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- DBXFWLGYJVBDGS-UHFFFAOYSA-N n-(2,3-dimethylphenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C(=C(C)C=CC=2)C)=C1C DBXFWLGYJVBDGS-UHFFFAOYSA-N 0.000 description 1
- JLBRPUWVDHSZKB-UHFFFAOYSA-N n-(2,3-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(C)=C1C JLBRPUWVDHSZKB-UHFFFAOYSA-N 0.000 description 1
- GSCVNZDWYVYWKH-UHFFFAOYSA-N n-(2,5-dimethylphenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound CC1=CC=C(C)C(NC(=O)C=2C(C=C(C)OC=2C)=O)=C1 GSCVNZDWYVYWKH-UHFFFAOYSA-N 0.000 description 1
- XTTATAWSHOUFDE-UHFFFAOYSA-N n-(2,6-diethylphenyl)-2,6-dimethyl-4-oxo-3h-pyran-2-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1(C)OC(C)=CC(=O)C1 XTTATAWSHOUFDE-UHFFFAOYSA-N 0.000 description 1
- RHMZPMLEBQIVSB-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C(=CC=CC=2C)C)=C1C RHMZPMLEBQIVSB-UHFFFAOYSA-N 0.000 description 1
- NDVRDNPIOIFXSL-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=C(C)C=CC=C1C NDVRDNPIOIFXSL-UHFFFAOYSA-N 0.000 description 1
- WHNJMYKDHMHVRL-UHFFFAOYSA-N n-(2-chlorophenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C(=CC=CC=2)Cl)=C1C WHNJMYKDHMHVRL-UHFFFAOYSA-N 0.000 description 1
- CVGQCYBKOJGFPL-UHFFFAOYSA-N n-(2-ethyl-6-methylphenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)C1=C(C)OC(C)=CC1=O CVGQCYBKOJGFPL-UHFFFAOYSA-N 0.000 description 1
- TXIFNAIHABCDSX-UHFFFAOYSA-N n-(2-ethyl-6-methylphenyl)-3-oxobutanamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)CC(C)=O TXIFNAIHABCDSX-UHFFFAOYSA-N 0.000 description 1
- XHRXNFJKSRHYKE-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C(=C(Cl)C=CC=2)C)=C1C XHRXNFJKSRHYKE-UHFFFAOYSA-N 0.000 description 1
- GQGJXQLDRPIMPL-UHFFFAOYSA-N n-(4-chlorophenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=C1C GQGJXQLDRPIMPL-UHFFFAOYSA-N 0.000 description 1
- FQSJQWOMTGDXHO-UHFFFAOYSA-N n-(4-methoxyphenyl)-2,6-dimethyl-4-oxopyran-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)OC(C)=CC1=O FQSJQWOMTGDXHO-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N43/14—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 six-membered rings
- A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
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)
- Pyrane Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27897384A JPS61158977A (ja) | 1984-12-29 | 1984-12-29 | ピロン−３−カルボキサミド化合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3544850A1 true DE3544850A1 (de) | 1986-07-10 |
Family
ID=17604644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853544850 Withdrawn DE3544850A1 (de) | 1984-12-29 | 1985-12-18 | Pyron-3-carboxamidverbindungen |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS61158977A (enrdf_load_stackoverflow) |
| DE (1) | DE3544850A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2575471B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2169290B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH064614B2 (ja) * | 1985-01-10 | 1994-01-19 | ダイセル化学工業株式会社 | ４−オキソ−４ｈ−ピラン−３−カルボキサミド化合物の製造法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH064614B2 (ja) * | 1985-01-10 | 1994-01-19 | ダイセル化学工業株式会社 | ４−オキソ−４ｈ−ピラン−３−カルボキサミド化合物の製造法 |
-
1984
- 1984-12-29 JP JP27897384A patent/JPS61158977A/ja active Granted
-
1985
- 1985-12-16 GB GB08530927A patent/GB2169290B/en not_active Expired
- 1985-12-17 FR FR8518708A patent/FR2575471B1/fr not_active Expired
- 1985-12-18 DE DE19853544850 patent/DE3544850A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2169290B (en) | 1988-03-30 |
| FR2575471B1 (fr) | 1988-07-15 |
| GB8530927D0 (en) | 1986-01-29 |
| JPS61158977A (ja) | 1986-07-18 |
| FR2575471A1 (fr) | 1986-07-04 |
| GB2169290A (en) | 1986-07-09 |
| JPH0557987B2 (enrdf_load_stackoverflow) | 1993-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |