CA1108161A - Fungicidally active cyclopropanecarboxylic acid anilides - Google Patents
Fungicidally active cyclopropanecarboxylic acid anilidesInfo
- Publication number
- CA1108161A CA1108161A CA303,250A CA303250A CA1108161A CA 1108161 A CA1108161 A CA 1108161A CA 303250 A CA303250 A CA 303250A CA 1108161 A CA1108161 A CA 1108161A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- anilide
- furyl
- oxoperhydro
- cyclo
- 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.)
- Expired
Links
- OCHYJSATRBHPLB-UHFFFAOYSA-N n-phenylcyclopropanecarboxamide Chemical class C1CC1C(=O)NC1=CC=CC=C1 OCHYJSATRBHPLB-UHFFFAOYSA-N 0.000 title abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 94
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 45
- 241000233866 Fungi Species 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- -1 dimethylphenyl Chemical group 0.000 claims description 24
- 230000003032 phytopathogenic effect Effects 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 230000002633 protecting effect Effects 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003931 anilides Chemical class 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ADEJVZGOEKLICZ-UHFFFAOYSA-N C(C)C1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 Chemical compound C(C)C1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 ADEJVZGOEKLICZ-UHFFFAOYSA-N 0.000 claims description 3
- WQMRIGLEHRHANC-UHFFFAOYSA-N C(C)C1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 Chemical compound C(C)C1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 WQMRIGLEHRHANC-UHFFFAOYSA-N 0.000 claims description 3
- YOTZIJATADZFHT-UHFFFAOYSA-N C(C)C=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 Chemical compound C(C)C=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 YOTZIJATADZFHT-UHFFFAOYSA-N 0.000 claims description 3
- FVTSQWATRFFSHH-UHFFFAOYSA-N C1CC1C(=O)N(C2CCOC2=O)C3=CC(=CC=C3)F Chemical compound C1CC1C(=O)N(C2CCOC2=O)C3=CC(=CC=C3)F FVTSQWATRFFSHH-UHFFFAOYSA-N 0.000 claims description 3
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 claims description 3
- CCMUXDKGKNRNKV-UHFFFAOYSA-N O=C1OCCC1N(C1=CC=CC=C1)C(=O)C1CC1 Chemical compound O=C1OCCC1N(C1=CC=CC=C1)C(=O)C1CC1 CCMUXDKGKNRNKV-UHFFFAOYSA-N 0.000 claims description 3
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 claims description 3
- NWRQSRBUSAOGOZ-UHFFFAOYSA-N BrC=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 Chemical compound BrC=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 NWRQSRBUSAOGOZ-UHFFFAOYSA-N 0.000 claims description 2
- JCJQYWUPDCLNNR-UHFFFAOYSA-N C1=CC(Cl)=CC=C1N(C(=O)C1CC1)C1C(=O)OCC1 Chemical compound C1=CC(Cl)=CC=C1N(C(=O)C1CC1)C1C(=O)OCC1 JCJQYWUPDCLNNR-UHFFFAOYSA-N 0.000 claims description 2
- PYOVAOKTESDFRI-UHFFFAOYSA-N C1CC1C(=O)N(C2CCOC2=O)C3=CC=CC(=C3)C#N Chemical compound C1CC1C(=O)N(C2CCOC2=O)C3=CC=CC(=C3)C#N PYOVAOKTESDFRI-UHFFFAOYSA-N 0.000 claims description 2
- GJMONPSULDEHGJ-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C(=CC=C1)C GJMONPSULDEHGJ-UHFFFAOYSA-N 0.000 claims description 2
- ACWNSQYNWQANLI-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC(=C1)C Chemical compound CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC(=C1)C ACWNSQYNWQANLI-UHFFFAOYSA-N 0.000 claims description 2
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- JBEUCYNJVCMGDV-UHFFFAOYSA-N FC1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 Chemical compound FC1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 JBEUCYNJVCMGDV-UHFFFAOYSA-N 0.000 claims description 2
- ZCEQTRBOJBOALR-UHFFFAOYSA-N N-(4-methoxyphenyl)-N-(2-oxooxolan-3-yl)cyclopropanecarboxamide Chemical compound C1=CC(OC)=CC=C1N(C(=O)C1CC1)C1C(=O)OCC1 ZCEQTRBOJBOALR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
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- UDXRRSKAFPKOJO-UHFFFAOYSA-N CC1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 Chemical compound CC1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 UDXRRSKAFPKOJO-UHFFFAOYSA-N 0.000 claims 1
- KGVDHPKIECPMKY-UHFFFAOYSA-N CC=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 Chemical compound CC=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 KGVDHPKIECPMKY-UHFFFAOYSA-N 0.000 claims 1
- LGOYBDKCFHJDOO-UHFFFAOYSA-N COC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 Chemical compound COC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 LGOYBDKCFHJDOO-UHFFFAOYSA-N 0.000 claims 1
- CHPYXJXCEADFQC-UHFFFAOYSA-N ClC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1Cl Chemical compound ClC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1Cl CHPYXJXCEADFQC-UHFFFAOYSA-N 0.000 claims 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2724786.5 | 1977-05-27 | ||
| DE2724786A DE2724786C2 (de) | 1977-05-27 | 1977-05-27 | Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108161A true CA1108161A (en) | 1981-09-01 |
Family
ID=6010435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA303,250A Expired CA1108161A (en) | 1977-05-27 | 1978-05-12 | Fungicidally active cyclopropanecarboxylic acid anilides |
Country Status (39)
| Country | Link |
|---|---|
| JP (1) | JPS53147061A (cs) |
| AR (1) | AR220710A1 (cs) |
| AT (1) | AT360803B (cs) |
| AU (1) | AU520353B2 (cs) |
| BE (1) | BE867556A (cs) |
| BG (1) | BG28688A3 (cs) |
| BR (1) | BR7803382A (cs) |
| CA (1) | CA1108161A (cs) |
| CH (1) | CH633784A5 (cs) |
| CS (1) | CS203192B2 (cs) |
| CY (1) | CY1163A (cs) |
| DD (1) | DD136093A5 (cs) |
| DE (1) | DE2724786C2 (cs) |
| DK (1) | DK233878A (cs) |
| EG (1) | EG13373A (cs) |
| ES (1) | ES470195A1 (cs) |
| FI (1) | FI68397C (cs) |
| FR (1) | FR2392019A1 (cs) |
| GB (1) | GB1603730A (cs) |
| GR (1) | GR72966B (cs) |
| HU (1) | HU184201B (cs) |
| IE (1) | IE46923B1 (cs) |
| IL (1) | IL54719A (cs) |
| IT (1) | IT1096326B (cs) |
| KE (1) | KE3241A (cs) |
| LU (1) | LU79711A1 (cs) |
| MX (1) | MX5224E (cs) |
| MY (1) | MY8300210A (cs) |
| NL (1) | NL7805404A (cs) |
| NO (1) | NO149430C (cs) |
| PH (1) | PH15700A (cs) |
| PL (1) | PL110646B1 (cs) |
| PT (1) | PT68075B (cs) |
| RO (1) | RO75072A (cs) |
| SE (1) | SE442868B (cs) |
| SU (2) | SU784770A3 (cs) |
| TR (1) | TR20568A (cs) |
| YU (1) | YU40192B (cs) |
| ZA (1) | ZA783036B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440780A (en) * | 1979-06-01 | 1984-04-03 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones |
| EP0016985A1 (de) * | 1979-03-16 | 1980-10-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Substituierte Anilide, Verfahren zu deren Herstellung, fungicide Mittel enthaltend solche Verbindungen sowie Verwendung solcher Verbindungen bzw. Mittel zur Bekämpfung von Pflanzenfungi |
| DE2920435A1 (de) * | 1979-05-19 | 1980-12-04 | Basf Ag | 2-aminopropanalacetale, verfahren zu ihrer herstellung, ihre anwendung als fungizide und verfahren zur herstellung von substituierten anilinen |
| US4599351A (en) * | 1981-08-14 | 1986-07-08 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino) lactones |
| JPS61186735U (cs) * | 1985-05-14 | 1986-11-21 |
-
1977
- 1977-05-27 DE DE2724786A patent/DE2724786C2/de not_active Expired
-
1978
- 1978-04-24 FI FI781264A patent/FI68397C/fi not_active IP Right Cessation
- 1978-05-09 YU YU1102/78A patent/YU40192B/xx unknown
- 1978-05-11 MX MX787079U patent/MX5224E/es unknown
- 1978-05-12 CA CA303,250A patent/CA1108161A/en not_active Expired
- 1978-05-15 PH PH21136A patent/PH15700A/en unknown
- 1978-05-16 IL IL54719A patent/IL54719A/xx unknown
- 1978-05-18 NL NL7805404A patent/NL7805404A/xx not_active Application Discontinuation
- 1978-05-18 TR TR20568A patent/TR20568A/xx unknown
- 1978-05-23 PT PT68075A patent/PT68075B/pt unknown
- 1978-05-23 GB GB21326/78A patent/GB1603730A/en not_active Expired
- 1978-05-23 CY CY1163A patent/CY1163A/en unknown
- 1978-05-24 IE IE1029/78A patent/IE46923B1/en unknown
- 1978-05-24 EG EG333/78A patent/EG13373A/xx active
- 1978-05-24 JP JP6212278A patent/JPS53147061A/ja active Granted
- 1978-05-24 PL PL1978207069A patent/PL110646B1/pl unknown
- 1978-05-24 AR AR272308A patent/AR220710A1/es active
- 1978-05-24 AT AT380578A patent/AT360803B/de not_active IP Right Cessation
- 1978-05-24 ES ES470195A patent/ES470195A1/es not_active Expired
- 1978-05-25 SE SE7805994A patent/SE442868B/sv not_active IP Right Cessation
- 1978-05-25 LU LU79711A patent/LU79711A1/de unknown
- 1978-05-25 IT IT23774/78A patent/IT1096326B/it active
- 1978-05-25 RO RO7894166A patent/RO75072A/ro unknown
- 1978-05-25 DD DD78205587A patent/DD136093A5/xx unknown
- 1978-05-25 CS CS783406A patent/CS203192B2/cs unknown
- 1978-05-26 GR GR56344A patent/GR72966B/el unknown
- 1978-05-26 BR BR7803382A patent/BR7803382A/pt unknown
- 1978-05-26 CH CH580678A patent/CH633784A5/de not_active IP Right Cessation
- 1978-05-26 BE BE188101A patent/BE867556A/xx not_active IP Right Cessation
- 1978-05-26 SU SU782621101A patent/SU784770A3/ru active
- 1978-05-26 AU AU36529/78A patent/AU520353B2/en not_active Expired
- 1978-05-26 HU HU78SCHE646A patent/HU184201B/hu unknown
- 1978-05-26 SU SU782621053A patent/SU727107A3/ru active
- 1978-05-26 FR FR7815747A patent/FR2392019A1/fr active Granted
- 1978-05-26 BG BG039862A patent/BG28688A3/xx unknown
- 1978-05-26 NO NO781838A patent/NO149430C/no unknown
- 1978-05-26 DK DK233878A patent/DK233878A/da not_active Application Discontinuation
- 1978-05-26 ZA ZA00783036A patent/ZA783036B/xx unknown
-
1982
- 1982-10-28 KE KE3241A patent/KE3241A/xx unknown
-
1983
- 1983-12-30 MY MY210/83A patent/MY8300210A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |