CA1113857A - 1-acryloyl-3-(substituted)phenyl ureas - Google Patents
1-acryloyl-3-(substituted)phenyl ureasInfo
- Publication number
- CA1113857A CA1113857A CA319,369A CA319369A CA1113857A CA 1113857 A CA1113857 A CA 1113857A CA 319369 A CA319369 A CA 319369A CA 1113857 A CA1113857 A CA 1113857A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- acryloyl
- lbs
- methyl
- fungicide
- 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
- -1 1-acryloyl-3-(substituted)phenyl ureas Chemical class 0.000 title claims abstract description 9
- 235000013877 carbamide Nutrition 0.000 title abstract description 10
- 239000003973 paint Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 235000008504 concentrate Nutrition 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000012871 anti-fungal composition Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 15
- 239000004033 plastic Substances 0.000 abstract description 5
- 229920003023 plastic Polymers 0.000 abstract description 5
- 230000000855 fungicidal effect Effects 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001136494 Talaromyces funiculosus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241001103808 Albifimbria verrucaria Species 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000228153 Penicillium citrinum Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- AWYFNIZYMPNGAI-UHFFFAOYSA-L ethylenebis(dithiocarbamate) Chemical compound [S-]C(=S)NCCNC([S-])=S AWYFNIZYMPNGAI-UHFFFAOYSA-L 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000008261 styrofoam Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 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
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229940093635 tributyl phosphate Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Biochemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Textile Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US87525378A | 1978-02-06 | 1978-02-06 | |
US875,253 | 1978-02-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1113857A true CA1113857A (en) | 1981-12-08 |
Family
ID=25365465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA319,369A Expired CA1113857A (en) | 1978-02-06 | 1979-01-09 | 1-acryloyl-3-(substituted)phenyl ureas |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS54110324A (enrdf_load_html_response) |
AU (1) | AU521539B2 (enrdf_load_html_response) |
CA (1) | CA1113857A (enrdf_load_html_response) |
DE (1) | DE2904309A1 (enrdf_load_html_response) |
FR (1) | FR2415962A1 (enrdf_load_html_response) |
GB (1) | GB2015342B (enrdf_load_html_response) |
PH (1) | PH16330A (enrdf_load_html_response) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2929863A1 (de) * | 1979-07-24 | 1981-02-19 | Bayer Ag | Neue n-aryl-n'-acryloylureide, ein verfahren zu ihrer herstellung und ihre verwendung |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE888316C (de) * | 1943-12-25 | 1953-08-31 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Arylacrylharnstoffen und daraus abgeleiteten Polymerisaten |
GB1221116A (en) * | 1967-05-15 | 1971-02-03 | Armour Grocery Products Compan | Antiseptic detergent compositions comprising n-acyl-n'-(halogenated) aryl ureas |
DE2059872A1 (de) * | 1970-12-05 | 1972-06-15 | Merck Patent Gmbh | Thioharnstoffe,Verfahren zu ihrer Herstellung und ihre Verwendung zur Schaedlingsbekaempfung |
DE2512171A1 (de) * | 1975-03-20 | 1976-10-14 | Bayer Ag | 2,3-dihalogen-alkanoyl-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
-
1979
- 1979-01-09 CA CA319,369A patent/CA1113857A/en not_active Expired
- 1979-01-10 AU AU43244/79A patent/AU521539B2/en not_active Ceased
- 1979-01-18 JP JP347479A patent/JPS54110324A/ja active Pending
- 1979-01-18 PH PH22078A patent/PH16330A/en unknown
- 1979-01-31 FR FR7902540A patent/FR2415962A1/fr active Granted
- 1979-02-05 GB GB7903963A patent/GB2015342B/en not_active Expired
- 1979-02-05 DE DE19792904309 patent/DE2904309A1/de active Granted
Also Published As
Publication number | Publication date |
---|---|
GB2015342A (en) | 1979-09-12 |
AU521539B2 (en) | 1982-04-08 |
GB2015342B (en) | 1982-05-19 |
FR2415962B1 (enrdf_load_html_response) | 1984-02-17 |
FR2415962A1 (fr) | 1979-08-31 |
AU4324479A (en) | 1979-08-16 |
JPS54110324A (en) | 1979-08-29 |
PH16330A (en) | 1983-09-05 |
DE2904309C2 (enrdf_load_html_response) | 1989-04-27 |
DE2904309A1 (de) | 1979-09-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MKEX | Expiry |