GB936342A - Salts of esterified 8-hydroxyquinolines, an intermediate therefor and fungicidal compositions containing such salts - Google Patents
Salts of esterified 8-hydroxyquinolines, an intermediate therefor and fungicidal compositions containing such saltsInfo
- Publication number
- GB936342A GB936342A GB2994959A GB2994959A GB936342A GB 936342 A GB936342 A GB 936342A GB 2994959 A GB2994959 A GB 2994959A GB 2994959 A GB2994959 A GB 2994959A GB 936342 A GB936342 A GB 936342A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salts
- acid
- methyl
- esters
- group
- 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
- 150000003839 salts Chemical class 0.000 title abstract 11
- 230000000855 fungicidal effect Effects 0.000 title abstract 4
- 150000004325 8-hydroxyquinolines Chemical class 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 10
- -1 quinolyl ester Chemical class 0.000 abstract 6
- 239000005725 8-Hydroxyquinoline Substances 0.000 abstract 5
- 229960003540 oxyquinoline Drugs 0.000 abstract 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 4
- 238000002360 preparation method Methods 0.000 abstract 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 3
- 239000000725 suspension Substances 0.000 abstract 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229920000180 alkyd Polymers 0.000 abstract 2
- BHKPHCKISVSDGV-UHFFFAOYSA-N benzoic acid 8-quinolinyl ester Chemical compound C=1C=CC2=CC=CN=C2C=1OC(=O)C1=CC=CC=C1 BHKPHCKISVSDGV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 2
- QWNQXYWOJJCPDX-UHFFFAOYSA-N diquinolin-8-yl benzene-1,2-dicarboxylate Chemical compound N1=CC=CC2=CC=CC(=C12)OC(C=1C(C(=O)OC=2C=CC=C3C=CC=NC23)=CC=CC1)=O QWNQXYWOJJCPDX-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000417 fungicide Substances 0.000 abstract 2
- 239000002674 ointment Substances 0.000 abstract 2
- 239000003973 paint Substances 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 238000004078 waterproofing Methods 0.000 abstract 2
- 239000001993 wax Substances 0.000 abstract 2
- RXNOYRCWKRFNIM-UHFFFAOYSA-N 2-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Cl)=O RXNOYRCWKRFNIM-UHFFFAOYSA-N 0.000 abstract 1
- OYUKRQOCPFZNHR-UHFFFAOYSA-N 4-methylquinolin-8-ol Chemical class C1=CC=C2C(C)=CC=NC2=C1O OYUKRQOCPFZNHR-UHFFFAOYSA-N 0.000 abstract 1
- 229920001817 Agar Polymers 0.000 abstract 1
- POSLNLCLPMMCQH-UHFFFAOYSA-N C(C=1C(O)=CC=CC1)(=O)O.C(C1=CC=CC=C1)(=O)OC=1C=CC=C2C=CC=NC12 Chemical compound C(C=1C(O)=CC=CC1)(=O)O.C(C1=CC=CC=C1)(=O)OC=1C=CC=C2C=CC=NC12 POSLNLCLPMMCQH-UHFFFAOYSA-N 0.000 abstract 1
- 244000025254 Cannabis sativa Species 0.000 abstract 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 abstract 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 abstract 1
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical class FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 abstract 1
- 206010017533 Fungal infection Diseases 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 208000031888 Mycoses Diseases 0.000 abstract 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 239000008272 agar Substances 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012871 anti-fungal composition Substances 0.000 abstract 1
- OAOXPQKIXSVSRH-UHFFFAOYSA-N butanedioic acid;propanedioic acid Chemical class OC(=O)CC(O)=O.OC(=O)CCC(O)=O OAOXPQKIXSVSRH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 235000010216 calcium carbonate Nutrition 0.000 abstract 1
- 235000009120 camo Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 235000005607 chanvre indien Nutrition 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 239000011487 hemp Substances 0.000 abstract 1
- 239000012770 industrial material Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical class [Hg]C1=CC=CC=C1 DCNLOVYDMCVNRZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005493 quinolyl group Chemical class 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 235000015096 spirit Nutrition 0.000 abstract 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 abstract 1
- 201000004647 tinea pedis Diseases 0.000 abstract 1
- 239000003981 vehicle Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyd resin and polyvinyl acetate paints comprise as a fungicide a salicylic acid salt of a quinolyl ester having one of the general formulae: <FORM:0936342/IV(a)/1> wherein R is the acyl group of a monocarboxylic acid, R1 is the diacyl group of a dicarboxylic acid and X is hydrogen, halogen or a C1-8 alkyl or alkoxy group. In examples, the salicylic acid salt of 8-benzoyloxy quinoline is incorporated in an alkyd resin paint comprising also an aliphatic hydrocarbon vehicle, driers, Ti-Ca pigment, TiO2, CaCO3 and silica. A fungicidal ointment comprises the 8-benzoyloxy quinoline salicylate, dipropylene glycol and polyethylene glycol 1,000.ALSO:The invention comprises salicylic acid salts of mono- and di-carboxylic acid esters of an 8-hydroxy quinoline having the general formulae <FORM:0936342/IV(a)/1> wherein R and R1 are the acyl groups of a monocarboxylic acid and a dicarboxylic acid respectively, and X is hydrogen, halogen or an alkyl or alkoxy group having from 1 to 8 carbon atoms. The invention also comprises di-8-quinolyl phthalate and its preparation by reacting 8-hydroxy quinoline with phthalic acid chloride in pyridine. The salicylic acid salts are prepared by reacting the acid with the desired ester in an organic solvent. Examples describe the preparation of the salicyclic acid salts of the benzoic, phthalic, butyric and palmitic esters of 8-hydroxy quinoline and of the benzoic esters of 3-methyl, 4-methyl, 5-methyl, 4-chloro and 5-chloro substituted 8-hydroxy quinoline, by dissolving the salicyclic acid and ester in hot isopropanol, benzene, petroleum ether or mineral spirits and cooling to crystallise out the desired salt. The preparation of di-8-quinolyl phthalate and the benzoates of 3-methyl and 4-methyl 8-hydroxy quinolines from the acid chlorides is described in detail. Reference is made to the use of 8-quinolyl esters of various other carboxylic acids including acetic, butyl acetic, cyclohexyl-, cyclopentyl- and phenyl-acetic, cinnamic, furoic, malonic acid succinic acids. The ester salts may be used as active components in antifungal compositions (see Group VI).ALSO:Fabric, leather, wood, hemp and paper are proofed against attack by fungi by applying thereto salicylic acid salts of quinolyl esters having one of the formula <FORM:0936342/IV(a)/1> wherein R is the acyl group of a monocarboxylic acid, R1 is the diacyl group of a dicarboxylic acid and X is hydrogen, halogen or a C1-8 alkyl or alkoxy group, the salts being used in solution or suspension. The salicylic acid salts of the benzoic, phthalic, butyric, and palmitic esters of 8-hydroxy quinoline and of the benzoic acid esters of 3-methyl, 4-methyl, 5-methyl, 4-chloro and 5-chloro substituted 8-hydroxy quinolines are typical of the specified salts. The salts may be formulated with waterproofing waxes, resins and flame-proofing chemicals; other fungicides may also be present e.g., chlorinated phenols and phenyl mercury salts.ALSO:Fungicidal and bacteriocidal compositions comprise as active ingredient, a salicylic acid salt of a quinolyl ester having one of the formul : <FORM:0936342/VI/1> wherein R is the acyl group of a monocarboxylic acid, R1 is the diacyl group of a dicarboxylic acid and X is hydrogen, halogen or a C1-8 alkyl or alkoxy group. The salts may be used with a pharmaceutical carrier in the treatment of fungal infections, e.g. athlete's foot. Specified pharmaceutical compositions are (1) an ointment comprising the salicylic acid salt of 8-benzoyloxy quinoline, dipropylene glycol and polyethylene glycol 1000; (2) a solution of the same salt in dipropylene glycol containing malt agar and (3) an aerosol of the same salt and dipropylene glycol in a mixture of chlorofluoro methanes. Also, the salts may be used in solution or suspension in a solvent, e.g. water, in proofing industrial material subject to attack by micro-organisms (see Groups IV (a) and IV (c)); such solutions and suspensions may also comprise water-proofing waxes, resins and flame-proofing chemicals. Numerous other examples of the salts are provided and their preparation is described (see Group IV (b)).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75855558A | 1958-09-02 | 1958-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB936342A true GB936342A (en) | 1963-09-11 |
Family
ID=25052158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2994959A Expired GB936342A (en) | 1958-09-02 | 1959-09-02 | Salts of esterified 8-hydroxyquinolines, an intermediate therefor and fungicidal compositions containing such salts |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH362693A (en) |
| DE (1) | DE1223393B (en) |
| GB (1) | GB936342A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0747362A1 (en) * | 1995-06-05 | 1996-12-11 | American Cyanamid Company | Substituted quinoline herbicide intermediates and process |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107827814B (en) * | 2017-11-24 | 2021-04-20 | 安徽恒星制药有限公司 | Preparation method of dequalinium chloride crystal form A |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE891257C (en) * | 1950-05-16 | 1953-09-28 | Ciba Geigy | Process for the preparation of new esters of oxyquinolines |
-
1959
- 1959-09-01 DE DEM42591A patent/DE1223393B/en active Pending
- 1959-09-02 CH CH7770759A patent/CH362693A/en unknown
- 1959-09-02 GB GB2994959A patent/GB936342A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0747362A1 (en) * | 1995-06-05 | 1996-12-11 | American Cyanamid Company | Substituted quinoline herbicide intermediates and process |
| US5633380A (en) * | 1995-06-05 | 1997-05-27 | American Cyanamid Company | Substituted quinoline herbicide intermediates and process |
| AU712554B2 (en) * | 1995-06-05 | 1999-11-11 | American Cyanamid Company | Substituted quinoline herbicide intermediates and process |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1223393B (en) | 1966-08-25 |
| CH362693A (en) | 1962-06-30 |
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