CH645514A5 - N-acil-s-aloalchil (o s-alovinil)-tiolcarbammati fungicidi. - Google Patents
N-acil-s-aloalchil (o s-alovinil)-tiolcarbammati fungicidi. Download PDFInfo
- Publication number
- CH645514A5 CH645514A5 CH602880A CH602880A CH645514A5 CH 645514 A5 CH645514 A5 CH 645514A5 CH 602880 A CH602880 A CH 602880A CH 602880 A CH602880 A CH 602880A CH 645514 A5 CH645514 A5 CH 645514A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- compounds
- carbamate
- benzoyl
- compound according
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 208000015181 infectious disease Diseases 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 206010017533 Fungal infection Diseases 0.000 claims description 8
- 208000031888 Mycoses Diseases 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 244000045561 useful plants Species 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 241000235349 Ascomycota Species 0.000 claims 1
- 241000221198 Basidiomycota Species 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000003449 preventive effect Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000221577 Uromyces appendiculatus Species 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 230000000855 fungicidal effect Effects 0.000 description 4
- 241000123650 Botrytis cinerea Species 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 235000010234 sodium benzoate Nutrition 0.000 description 3
- 239000004299 sodium benzoate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- AUFXRXYJUOWJSO-UHFFFAOYSA-N CN=S(C(Cl)(Cl)Cl)=C(O)Cl Chemical compound CN=S(C(Cl)(Cl)Cl)=C(O)Cl AUFXRXYJUOWJSO-UHFFFAOYSA-N 0.000 description 1
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ROLNQBRUSZZVNM-UHFFFAOYSA-N OC=S(C(Cl)(Cl)Cl)=NC1=CC=CC=C1 Chemical compound OC=S(C(Cl)(Cl)Cl)=NC1=CC=CC=C1 ROLNQBRUSZZVNM-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000000038 Ziziphus mauritiana Species 0.000 description 1
- 235000006545 Ziziphus mauritiana Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25144/79A IT1123524B (it) | 1979-08-16 | 1979-08-16 | N-acil-triclorometiltiocarbammati fungicidi |
| IT26341/79A IT1125454B (it) | 1979-10-09 | 1979-10-09 | N-acil-s-aloalchil (os-alovinil)-tiolcarbammati fungicidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH645514A5 true CH645514A5 (it) | 1984-10-15 |
Family
ID=26328568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH602880A CH645514A5 (it) | 1979-08-16 | 1980-08-08 | N-acil-s-aloalchil (o s-alovinil)-tiolcarbammati fungicidi. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4301174A (https=) |
| AR (1) | AR225455A1 (https=) |
| AU (1) | AU544372B2 (https=) |
| BR (1) | BR8005112A (https=) |
| CA (1) | CA1145764A (https=) |
| CH (1) | CH645514A5 (https=) |
| DE (1) | DE3030807A1 (https=) |
| ES (1) | ES8106140A1 (https=) |
| FR (1) | FR2463125A1 (https=) |
| GB (1) | GB2056980B (https=) |
| IL (1) | IL60797A (https=) |
| NL (1) | NL8004502A (https=) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2977209A (en) * | 1957-02-13 | 1961-03-28 | Stauffer Chemical Co | Method of combatting weeds |
| US3265563A (en) * | 1961-05-01 | 1966-08-09 | Stauffer Chemical Co | Phenyl nu-alkyl thiolcarbamate microbiocide |
| US3318947A (en) * | 1962-09-04 | 1967-05-09 | Monsanto Co | N-(alpha, alpha, alpha-trichloroacetyl)carbamates |
| US3288832A (en) * | 1963-09-23 | 1966-11-29 | Monsanto Co | Thiolcarbamate esters and method of preparation |
| US3845091A (en) * | 1972-08-14 | 1974-10-29 | Chevron Res | N-cyanoformyl thiolcarbamates |
| US4056594A (en) * | 1975-12-15 | 1977-11-01 | Phillips Petroleum Company | Method of producing a flexible extrudate of a mixture of poly(phenylene sulfide) and filler |
| US4056549A (en) * | 1976-06-07 | 1977-11-01 | Ppg Industries, Inc. | S-3-Methoxyphenyl N-alkylthiolcarbamates and S-3-methylthiophenyl N-alkylthiolcarbamates |
-
1980
- 1980-08-07 NL NL8004502A patent/NL8004502A/nl not_active Application Discontinuation
- 1980-08-08 CH CH602880A patent/CH645514A5/it not_active IP Right Cessation
- 1980-08-08 IL IL60797A patent/IL60797A/xx unknown
- 1980-08-11 FR FR8017653A patent/FR2463125A1/fr active Granted
- 1980-08-11 AU AU61318/80A patent/AU544372B2/en not_active Ceased
- 1980-08-12 AR AR281546A patent/AR225455A1/es active
- 1980-08-13 BR BR8005112A patent/BR8005112A/pt unknown
- 1980-08-14 ES ES494290A patent/ES8106140A1/es not_active Expired
- 1980-08-14 DE DE19803030807 patent/DE3030807A1/de not_active Ceased
- 1980-08-15 CA CA000358411A patent/CA1145764A/en not_active Expired
- 1980-08-15 GB GB8026775A patent/GB2056980B/en not_active Expired
- 1980-08-15 US US06/178,594 patent/US4301174A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4301174A (en) | 1981-11-17 |
| AU544372B2 (en) | 1985-05-23 |
| GB2056980A (en) | 1981-03-25 |
| FR2463125A1 (fr) | 1981-02-20 |
| IL60797A0 (en) | 1980-10-26 |
| AR225455A1 (es) | 1982-03-31 |
| BR8005112A (pt) | 1981-02-24 |
| GB2056980B (en) | 1983-08-10 |
| AU6131880A (en) | 1981-02-19 |
| CA1145764A (en) | 1983-05-03 |
| IL60797A (en) | 1984-05-31 |
| ES494290A0 (es) | 1981-07-16 |
| NL8004502A (nl) | 1981-02-18 |
| ES8106140A1 (es) | 1981-07-16 |
| FR2463125B1 (https=) | 1983-11-04 |
| DE3030807A1 (de) | 1981-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |