DE2604989A1 - 1,5-alkylen-3-aryl-hydantoin-derivate, verfahren zu ihrer herstellung und mittel mit herbizider und/oder fungizider wirkung - Google Patents
1,5-alkylen-3-aryl-hydantoin-derivate, verfahren zu ihrer herstellung und mittel mit herbizider und/oder fungizider wirkungInfo
- Publication number
- DE2604989A1 DE2604989A1 DE19762604989 DE2604989A DE2604989A1 DE 2604989 A1 DE2604989 A1 DE 2604989A1 DE 19762604989 DE19762604989 DE 19762604989 DE 2604989 A DE2604989 A DE 2604989A DE 2604989 A1 DE2604989 A1 DE 2604989A1
- Authority
- DE
- Germany
- Prior art keywords
- hydantoin
- general formula
- aryl
- tetramethylene
- alkylene
- 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- Withdrawn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
- 230000002363 herbicidal effect Effects 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 24
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title claims description 18
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229940091173 hydantoin Drugs 0.000 claims description 40
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 29
- -1 ITitro Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000001469 hydantoins Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000004009 herbicide Substances 0.000 description 13
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- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 6
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OSBIEFWIIINTNJ-UHFFFAOYSA-N 1,2-dichloro-4-isothiocyanatobenzene Chemical compound ClC1=CC=C(N=C=S)C=C1Cl OSBIEFWIIINTNJ-UHFFFAOYSA-N 0.000 description 1
- GOOCIVZVHKZJKH-UHFFFAOYSA-N 1-(4-ethoxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(OCC)=CC=C1N1C(=O)NC(=O)C1 GOOCIVZVHKZJKH-UHFFFAOYSA-N 0.000 description 1
- NMTNVDGKAGYQGH-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound COC1=CC=C(C=C1)N1C(=S)NC(=O)C1 NMTNVDGKAGYQGH-UHFFFAOYSA-N 0.000 description 1
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- SXJYSIBLFGQAND-UHFFFAOYSA-N 1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1 SXJYSIBLFGQAND-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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)
- Plural Heterocyclic Compounds (AREA)
- Eyeglasses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50016211A JPS5195134A (enExample) | 1975-02-10 | 1975-02-10 | |
| JP11803675A JPS5242893A (en) | 1975-09-30 | 1975-09-30 | Preparation of thiohydantoins |
| JP11803575A JPS5242877A (en) | 1975-09-30 | 1975-09-30 | Process for preparation of hydantoins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2604989A1 true DE2604989A1 (de) | 1976-08-19 |
Family
ID=27281290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762604989 Withdrawn DE2604989A1 (de) | 1975-02-10 | 1976-02-09 | 1,5-alkylen-3-aryl-hydantoin-derivate, verfahren zu ihrer herstellung und mittel mit herbizider und/oder fungizider wirkung |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1076114A (enExample) |
| CH (1) | CH624272A5 (enExample) |
| DE (1) | DE2604989A1 (enExample) |
| FR (1) | FR2300083A1 (enExample) |
| GB (1) | GB1503244A (enExample) |
| NL (1) | NL7601296A (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006633A1 (en) * | 1978-06-30 | 1980-01-09 | Mitsubishi Kasei Corporation | 6-(3,5-Dichlorophenyl)perhydroimidazo(5,1-b)thiazole derivatives, antifungal compositions and a method of controlling fungal infections in plants |
| US4358451A (en) * | 1979-04-26 | 1982-11-09 | Synthelabo | Pyrimido- and imidazo-pyridoindole derivatives |
| DE3137376A1 (de) * | 1981-09-19 | 1983-05-05 | Degussa Ag, 6000 Frankfurt | N-chlorcarbonyl-aminocarbonsaeureester, verfahren zu deren herstellung und deren verwendung |
| DE3213140A1 (de) * | 1982-04-08 | 1983-10-20 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Cycloalkan-5'-spiro-hydrantoine, ihre herstellung und verwendung |
| US4531964A (en) * | 1982-09-13 | 1985-07-30 | Nippon Kayaku Kabushiki Kaisha | Heterocyclic compound and a herbicidal composition containing said compound |
| US4911747A (en) * | 1983-08-02 | 1990-03-27 | American Cyanamid Co. | Herbicidal 3-thio-5H-imidazo[2,1-A]isoindole-3-(2H),5-diones |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK538477A (da) * | 1977-01-13 | 1978-07-14 | Du Pont | Herbicidt aktive substituerede bicycliske triazoler |
| DK156573C (da) * | 1981-06-16 | 1990-01-29 | Sumitomo Chemical Co | 2-(2-fluor-4-halogen-5-substitueret-phenyl)-hydantoinderivater, et herbicidt praeparat indeholdende disse, en fremgangsmaade til bekaempelse af ukrudt under anvendelse af disse samt anvendelse af disse som herbicid |
| US4439229A (en) * | 1981-06-29 | 1984-03-27 | Rohm And Haas Company | Substituted phthalimides herbicides |
| AU1787783A (en) * | 1982-09-02 | 1984-03-08 | Nippon Kayaku Kabushiki Kaisha | Nitrogen containing heterocyclic |
| DD270532A5 (de) * | 1986-12-10 | 1989-08-02 | �����@��������������@��������@������������@�K@�Kk�� | Verfahren zur herstellung von n-heterocyclisch substituierten benzofuranen und benzopyranen und diese verbindungen enthaltende herbizide zusammensetzung |
| DE3827221A1 (de) * | 1988-08-11 | 1990-02-15 | Bayer Ag | Substituierte n-phenyl-stickstoff- bzw. stickstoff-schwefel-heterocyclen, verfahren sowie entsprechende heterocyclische phenolderivate, phenyliso(thio)cyanate und -carbamate als zwischenprodukte zu ihrer herstellung, ihre verwendung in herbiziden und pflanzenwuchsregulierenden mitteln |
| US5221744A (en) * | 1991-05-17 | 1993-06-22 | Sandoz Ltd. | Arylaminocarbonyl compounds |
| CA2143937A1 (en) * | 1992-09-10 | 1994-03-17 | Degussa Aktiengesellschaft | Bicyclic imides as herbicides |
| AU1464101A (en) * | 1999-12-21 | 2001-07-03 | Gpi Nil Holdings, Inc. | Hydantoin derivative compounds, pharmaceutical compositions, and methods of using same |
| DE10051981A1 (de) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituierte Phenyluracile |
| WO2003011824A1 (en) | 2001-07-31 | 2003-02-13 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| US7405234B2 (en) | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| TW200407324A (en) * | 2002-05-17 | 2004-05-16 | Bristol Myers Squibb Co | Bicyclic modulators of androgen receptor function |
| AU2003302084A1 (en) | 2002-11-15 | 2004-06-15 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| BRPI0408420A (pt) | 2003-04-03 | 2006-03-21 | Merck Patent Gmbh | compostos de carbonila |
| US7820702B2 (en) | 2004-02-04 | 2010-10-26 | Bristol-Myers Squibb Company | Sulfonylpyrrolidine modulators of androgen receptor function and method |
| US7696241B2 (en) | 2004-03-04 | 2010-04-13 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| US7625923B2 (en) | 2004-03-04 | 2009-12-01 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445797A1 (de) * | 1964-12-31 | 1969-03-20 | Hoechst Ag | Verfahren zur Herstellung von Thiohydantoinen |
| JPS4916937B1 (enExample) * | 1970-01-21 | 1974-04-25 | ||
| JPS5136332B1 (enExample) * | 1970-12-09 | 1976-10-07 |
-
1976
- 1976-02-05 CA CA245,153A patent/CA1076114A/en not_active Expired
- 1976-02-09 FR FR7603459A patent/FR2300083A1/fr active Granted
- 1976-02-09 CH CH153276A patent/CH624272A5/fr not_active IP Right Cessation
- 1976-02-09 DE DE19762604989 patent/DE2604989A1/de not_active Withdrawn
- 1976-02-09 NL NL7601296A patent/NL7601296A/xx not_active Application Discontinuation
- 1976-02-10 GB GB512876A patent/GB1503244A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006633A1 (en) * | 1978-06-30 | 1980-01-09 | Mitsubishi Kasei Corporation | 6-(3,5-Dichlorophenyl)perhydroimidazo(5,1-b)thiazole derivatives, antifungal compositions and a method of controlling fungal infections in plants |
| US4229461A (en) | 1978-06-30 | 1980-10-21 | Mitsubishi Chemical Industries Limited | Fungicidal 6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivatives |
| US4358451A (en) * | 1979-04-26 | 1982-11-09 | Synthelabo | Pyrimido- and imidazo-pyridoindole derivatives |
| DE3137376A1 (de) * | 1981-09-19 | 1983-05-05 | Degussa Ag, 6000 Frankfurt | N-chlorcarbonyl-aminocarbonsaeureester, verfahren zu deren herstellung und deren verwendung |
| DE3213140A1 (de) * | 1982-04-08 | 1983-10-20 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Cycloalkan-5'-spiro-hydrantoine, ihre herstellung und verwendung |
| US4531964A (en) * | 1982-09-13 | 1985-07-30 | Nippon Kayaku Kabushiki Kaisha | Heterocyclic compound and a herbicidal composition containing said compound |
| US4911747A (en) * | 1983-08-02 | 1990-03-27 | American Cyanamid Co. | Herbicidal 3-thio-5H-imidazo[2,1-A]isoindole-3-(2H),5-diones |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7601296A (nl) | 1976-08-12 |
| FR2300083A1 (fr) | 1976-09-03 |
| CA1076114A (en) | 1980-04-22 |
| FR2300083B1 (enExample) | 1979-05-04 |
| GB1503244A (en) | 1978-03-08 |
| CH624272A5 (en) | 1981-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |