JPS61158977A - ピロン−３−カルボキサミド化合物 - Google Patents
ピロン−３−カルボキサミド化合物Info
- Publication number
- JPS61158977A JPS61158977A JP27897384A JP27897384A JPS61158977A JP S61158977 A JPS61158977 A JP S61158977A JP 27897384 A JP27897384 A JP 27897384A JP 27897384 A JP27897384 A JP 27897384A JP S61158977 A JPS61158977 A JP S61158977A
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- formula
- carboxamide
- dimethyl
- bilane
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 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
- 239000000126 substance Substances 0.000 claims 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 229910052736 halogen Chemical group 0.000 abstract description 2
- 150000002367 halogens Chemical group 0.000 abstract 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 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000005648 plant growth regulator Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010992 reflux Methods 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
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- -1 2-piperidino, 2-hexahydroazepinyl Chemical group 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHANVDZCDNSILX-UHFFFAOYSA-N n-phenylbutanamide Chemical class CCCC(=O)NC1=CC=CC=C1 UHANVDZCDNSILX-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000003756 stirring Methods 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 Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 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
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229940053202 antiepileptics carboxamide derivative Drugs 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 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
- 239000005645 nematicide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (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)
Priority Applications (4)
| 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 |
| GB08530927A GB2169290B (en) | 1984-12-29 | 1985-12-16 | Pyrone -3- carboxamide derivatives |
| FR8518708A FR2575471B1 (fr) | 1984-12-29 | 1985-12-17 | Composes de type pyrone-3-carboxamide et leur application pour inhiber la croissance des vegetaux |
| DE19853544850 DE3544850A1 (de) | 1984-12-29 | 1985-12-18 | Pyron-3-carboxamidverbindungen |
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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS61158977A true JPS61158977A (ja) | 1986-07-18 |
| JPH0557987B2 JPH0557987B2 (enrdf_load_stackoverflow) | 1993-08-25 |
Family
ID=17604644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27897384A Granted JPS61158977A (ja) | 1984-12-29 | 1984-12-29 | ピロン−３−カルボキサミド化合物 |
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 |
|---|---|
| FR2575471B1 (fr) | 1988-07-15 |
| GB2169290A (en) | 1986-07-09 |
| GB2169290B (en) | 1988-03-30 |
| GB8530927D0 (en) | 1986-01-29 |
| DE3544850A1 (de) | 1986-07-10 |
| FR2575471A1 (fr) | 1986-07-04 |
| JPH0557987B2 (enrdf_load_stackoverflow) | 1993-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0104532B1 (en) | O-halobenzoic acid derivatives, process for their preparation, herbicidal compositions and their use | |
| KR950012564B1 (ko) | N-인단일 카르복시아미드 유도체 및 이 유도체를 활성성분으로 함유하는 농업/원예용 살진균제 | |
| Zhang et al. | Synthesis and Biological Activity of N‐Aroyl (Aryloxyacetyl)‐N′‐ferrocenyl Thiourea Derivatives | |
| EP0382463B1 (en) | Maleimide compounds and fungicides containing them | |
| JPS61158977A (ja) | ピロン−３−カルボキサミド化合物 | |
| JPH02200658A (ja) | Ｎ―（置換）ベンジルカルボン酸アミド誘導体及び除草剤 | |
| US4730061A (en) | Pyrone-3-carboxamide compounds | |
| JPS5998004A (ja) | １，２，４―トリアゾール誘導体及び除草剤 | |
| JPH03106865A (ja) | ４―置換フェニル―１，２，４―トリアゾリン―５―オン誘導体及び農園芸用殺菌剤 | |
| US4568690A (en) | 1-Methyl-5-p-methylbenzoylpyrrole-2-acetamidoacetanilides with antiinflammatory, analgesic, antipyretic and anti-platelet aggregant activity | |
| US4002636A (en) | Certain novel substituted tetrahydro-oxothiazolo-triazolium compounds useful as herbicides | |
| JPH01221372A (ja) | 環状アシルヒドロキシルアミン誘導体 | |
| RU2810585C1 (ru) | Применение 2-хлор-N-(4-циано-3-цианометил-1Н-пиразол-5-ил)ацетамида в качестве антидота 2,4-Д на подсолнечнике | |
| US4725306A (en) | Pyridinecarboxamide plant growth inhibitors | |
| US4587348A (en) | Process for preparing herbicidal 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide | |
| EP0403703B1 (en) | Maleimide derivative, process for the preparation thereof, and agricultural and horticultural fungicide containing said maleimide derivative as active ingredient | |
| JP2515259B2 (ja) | ピロン−３−カルボキサミド化合物及び除草剤 | |
| US3475446A (en) | N-(5-nitro-2-thiazolyl)-cycloalkanecarboxamides | |
| US4744819A (en) | 4-oxo pyridinecarboxamide derivatives as plant growth regulators | |
| US3939174A (en) | Certain 3-oxo-2-aryl-5,6-dihydro-4(H)-pyrrolo-(1,2-C)(1,2,3)triazolium compounds | |
| JPS63115878A (ja) | ピロン−３−カルボキサミド誘導体及び除草剤 | |
| JPH021484A (ja) | ５，６―ジヒドロ―１，４，２―ジオキサジン誘導体および農園芸用殺菌剤 | |
| US3933843A (en) | Certain 1-substituted-4-oxo-3-substituted phenyl-1,2,3-triazolium compounds | |
| JP2671401B2 (ja) | α‐アミノチオアセトアミド誘導体およびその製造法 | |
| JPS604176B2 (ja) | ２，３−ジヒドロ−４（１ｈ）−キナゾリノン誘導体の製法 |