HU196105B - Fungicide compositions containing n-phenyl-carbamate derivatives as active components and process for producing anilide derivatives of n-phenyl-carbamate - Google Patents
Fungicide compositions containing n-phenyl-carbamate derivatives as active components and process for producing anilide derivatives of n-phenyl-carbamate Download PDFInfo
- Publication number
- HU196105B HU196105B HU841847A HU184784A HU196105B HU 196105 B HU196105 B HU 196105B HU 841847 A HU841847 A HU 841847A HU 184784 A HU184784 A HU 184784A HU 196105 B HU196105 B HU 196105B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- alkoxy
- halogen
- phenyl
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 46
- 230000000855 fungicidal effect Effects 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- 150000003931 anilides Chemical class 0.000 title claims description 5
- 239000000417 fungicide Substances 0.000 title abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- -1 cyclic imide Chemical class 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000005059 halophenyl group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 6
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 239000005909 Kieselgur Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005905 mesyloxy group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004969 haloethyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 101710088194 Dehydrogenase Proteins 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000006372 monohalo methyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract description 15
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 abstract description 14
- 241000233866 Fungi Species 0.000 abstract description 9
- 230000003032 phytopathogenic effect Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 93
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 230000003449 preventive effect Effects 0.000 description 24
- 238000009472 formulation Methods 0.000 description 20
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- 238000002474 experimental method Methods 0.000 description 18
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- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 15
- 240000008067 Cucumis sativus Species 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000013543 active substance Substances 0.000 description 13
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 13
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 12
- 239000005842 Thiophanate-methyl Substances 0.000 description 11
- 239000004495 emulsifiable concentrate Substances 0.000 description 11
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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- UINXPTPHAHVUCS-UHFFFAOYSA-N propan-2-yl n-(3,4-diethoxy-5-nitrophenyl)carbamate Chemical compound CCOC1=CC(NC(=O)OC(C)C)=CC([N+]([O-])=O)=C1OCC UINXPTPHAHVUCS-UHFFFAOYSA-N 0.000 description 1
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- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838313088A GB8313088D0 (en) | 1983-05-12 | 1983-05-12 | Fungicidal analine derivatives |
| JP18902583A JPS59210059A (ja) | 1983-05-12 | 1983-10-07 | アニリン誘導体，その製造法およびそれを有効成分とする農園芸用殺菌剤 |
| JP21851283A JPS59210064A (ja) | 1983-05-12 | 1983-11-18 | アニリン誘導体、その製造法およびそれを有効成分とする農園芸用殺菌剤 |
| JP22045083A JPS59210004A (ja) | 1983-05-12 | 1983-11-21 | 農園芸用殺菌組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT33950A HUT33950A (en) | 1985-01-28 |
| HU196105B true HU196105B (en) | 1988-10-28 |
Family
ID=27449474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU841847A HU196105B (en) | 1983-05-12 | 1984-05-11 | Fungicide compositions containing n-phenyl-carbamate derivatives as active components and process for producing anilide derivatives of n-phenyl-carbamate |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4752615A (en, 2012) |
| EP (1) | EP0125901B1 (en, 2012) |
| KR (2) | KR910009416B1 (en, 2012) |
| AU (1) | AU569077B2 (en, 2012) |
| BG (1) | BG43684A3 (en, 2012) |
| BR (1) | BR8402254A (en, 2012) |
| CA (1) | CA1256893A (en, 2012) |
| DE (1) | DE3476659D1 (en, 2012) |
| ES (1) | ES532464A0 (en, 2012) |
| GR (1) | GR81560B (en, 2012) |
| HU (1) | HU196105B (en, 2012) |
| IL (1) | IL71801A (en, 2012) |
| OA (1) | OA07768A (en, 2012) |
| RO (1) | RO90323A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA07768A (fr) * | 1983-05-12 | 1985-08-30 | Sumitomo Chemical Co | Dérivés d'anillines fongicides. |
| GB8315495D0 (en) * | 1983-06-06 | 1983-07-13 | Sumitomo Chemical Co | Fungicidal aniline derivatives |
| JP2533331B2 (ja) * | 1986-08-26 | 1996-09-11 | 住友化学工業株式会社 | カ―バメイト誘導体およびそれを有効成分とする農園芸用殺菌剤 |
| DE3804288A1 (de) * | 1987-06-03 | 1988-12-15 | Bayer Ag | Substituierte aminophenyl-carbamate |
| US5260474A (en) * | 1987-06-03 | 1993-11-09 | Bayer Aktiengesellschaft | Pesticidal substituted aminophenyl carbamates |
| DE4012712A1 (de) * | 1989-09-02 | 1991-05-02 | Bayer Ag | Derivate carbocyclischer anilide |
| US5237086A (en) * | 1989-09-02 | 1993-08-17 | Bayer Aktiengesellschaft | Fungicidal derivatives of carbocyclic anilides |
| DE4120904A1 (de) * | 1991-06-25 | 1993-01-07 | Bayer Ag | Acylierte aminophenol-derivate |
| JP3883566B2 (ja) * | 1992-01-29 | 2007-02-21 | ビーエーエスエフ アクチェンゲゼルシャフト | カルバメートおよびそれらを含む作物保護剤 |
| US5571443A (en) * | 1994-12-30 | 1996-11-05 | Buckman Laboratories International, Inc. | Synergistic combination of 2-(thiocyanomethylthio)benzothiazole and thiophanate compounds useful as fungicides |
| USD1054932S1 (en) * | 2022-08-18 | 2024-12-24 | Atieva, Inc. | Vehicle front chin splitter with sapphire logo |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2124037A1 (de) * | 1970-05-26 | 1971-12-02 | Monsanto Co , St Louis, Mo (V St A ) | Meta bifunktionelle Benzole und sie enthaltende herbicide Zubereitungen |
| US3933470A (en) * | 1972-06-30 | 1976-01-20 | American Cyanamid Company | Ester of (alkynyloxy)-, (alkenyloxy)-, and (cyanoalkoxy) carbanilic acids and their use as herbicides |
| NL7800026A (nl) * | 1977-01-07 | 1978-07-11 | Acna | Werkwijze voor de bereiding van gesubstitueerde amino-benzenen. |
| DE2703838A1 (de) * | 1977-01-31 | 1978-08-10 | Basf Ag | Diurethane |
| NZ200242A (en) * | 1981-04-16 | 1985-08-30 | Sumitomo Chemical Co | N-phenyl carbamates and fungicidal compositions |
| DE3378155D1 (de) * | 1982-07-27 | 1988-11-10 | Sumitomo Chemical Co | Fungicidal n-phenylcarbamate |
| OA07768A (fr) * | 1983-05-12 | 1985-08-30 | Sumitomo Chemical Co | Dérivés d'anillines fongicides. |
-
1984
- 1984-05-09 OA OA58293A patent/OA07768A/xx unknown
- 1984-05-10 GR GR74665A patent/GR81560B/el unknown
- 1984-05-10 IL IL71801A patent/IL71801A/xx unknown
- 1984-05-11 BG BG065478A patent/BG43684A3/xx unknown
- 1984-05-11 CA CA000454151A patent/CA1256893A/en not_active Expired
- 1984-05-11 EP EP84303201A patent/EP0125901B1/en not_active Expired
- 1984-05-11 HU HU841847A patent/HU196105B/hu not_active IP Right Cessation
- 1984-05-11 KR KR1019840002534A patent/KR910009416B1/ko not_active Expired
- 1984-05-11 DE DE8484303201T patent/DE3476659D1/de not_active Expired
- 1984-05-11 ES ES532464A patent/ES532464A0/es active Granted
- 1984-05-11 AU AU27931/84A patent/AU569077B2/en not_active Ceased
- 1984-05-11 RO RO84114515A patent/RO90323A/ro unknown
- 1984-11-12 BR BR8402254A patent/BR8402254A/pt unknown
-
1986
- 1986-11-13 US US06/930,082 patent/US4752615A/en not_active Expired - Fee Related
-
1991
- 1991-09-19 KR KR1019910016443A patent/KR920004578B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL71801A0 (en) | 1984-09-30 |
| DE3476659D1 (en) | 1989-03-16 |
| BR8402254A (pt) | 1984-12-18 |
| RO90323A (ro) | 1986-12-30 |
| EP0125901A1 (en) | 1984-11-21 |
| BG43684A3 (en) | 1988-07-15 |
| HUT33950A (en) | 1985-01-28 |
| OA07768A (fr) | 1985-08-30 |
| IL71801A (en) | 1989-10-31 |
| US4752615A (en) | 1988-06-21 |
| KR920004578B1 (ko) | 1992-06-11 |
| KR840009290A (ko) | 1984-12-26 |
| ES8505925A1 (es) | 1985-06-16 |
| AU569077B2 (en) | 1988-01-21 |
| CA1256893A (en) | 1989-07-04 |
| GR81560B (en, 2012) | 1984-12-11 |
| AU2793184A (en) | 1984-11-15 |
| ES532464A0 (es) | 1985-06-16 |
| EP0125901B1 (en) | 1989-02-08 |
| KR910009416B1 (ko) | 1991-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |