IE41829B1 - N-sulphenylated n-methyl-carbamates, process for their preparation, and their use as insecticides or acaricides - Google Patents
N-sulphenylated n-methyl-carbamates, process for their preparation, and their use as insecticides or acaricidesInfo
- Publication number
- IE41829B1 IE41829B1 IE2377/74A IE237774A IE41829B1 IE 41829 B1 IE41829 B1 IE 41829B1 IE 2377/74 A IE2377/74 A IE 2377/74A IE 237774 A IE237774 A IE 237774A IE 41829 B1 IE41829 B1 IE 41829B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- alkyl
- methyl
- scooch
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000000642 acaricide Substances 0.000 title description 2
- 239000002917 insecticide Substances 0.000 title description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000003085 diluting agent Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 239000011230 binding agent Substances 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
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- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
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- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
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- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
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- TXJXPZVVSLAQOQ-UHFFFAOYSA-N methyl chlorosulfanylformate Chemical compound COC(=O)SCl TXJXPZVVSLAQOQ-UHFFFAOYSA-N 0.000 abstract description 2
- WRBUEDBPGZVHJQ-UHFFFAOYSA-N n-methylcarbamoyl fluoride Chemical compound CNC(F)=O WRBUEDBPGZVHJQ-UHFFFAOYSA-N 0.000 abstract description 2
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
- OYAIUTQHMAEFEI-UHFFFAOYSA-N phenyl(sulfanyl)carbamic acid Chemical compound OC(=O)N(S)C1=CC=CC=C1 OYAIUTQHMAEFEI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 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
- 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
- NTJBWZHVSJNKAD-UHFFFAOYSA-N triethylazanium;fluoride Chemical compound [F-].CC[NH+](CC)CC NTJBWZHVSJNKAD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- 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
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2357930A DE2357930A1 (de) | 1973-11-20 | 1973-11-20 | N-sulfenylierte n-methyl-carbamate, verfahren zu ihrer herstellung und ihre insektizide und akarizide verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41829L IE41829L (en) | 1975-05-20 |
| IE41829B1 true IE41829B1 (en) | 1980-04-09 |
Family
ID=5898621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2377/74A IE41829B1 (en) | 1973-11-20 | 1974-11-19 | N-sulphenylated n-methyl-carbamates, process for their preparation, and their use as insecticides or acaricides |
Country Status (27)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4281011A (en) * | 1972-11-07 | 1981-07-28 | Bayer Aktiengesellschaft | Insecticidal N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid oxime esters |
| US4179514A (en) | 1976-05-20 | 1979-12-18 | Union Carbide Corporation | Ketoalkanesulfenyl and ketoalkanethiosulfenyl carbamates |
| US4234580A (en) * | 1977-03-28 | 1980-11-18 | Union Carbide Corporation | Carbamate thiosulfenylcarbamoyl fluoride compounds |
| US4131683A (en) * | 1978-05-12 | 1978-12-26 | Richardson-Merrell Inc. | ω-(1,3-Dithiolan-2-imino) substituted acetic acids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2113454A1 (de) * | 1971-03-19 | 1972-09-21 | Bayer Ag | Neue N-sulfenylierte Carbamate,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide,Akarizide und Fungizide |
| BE794366A (fr) * | 1972-01-22 | 1973-07-23 | Bayer Ag | Nouveaux carbamates d'oximes n-sulfenyles, leur procede de preparation et leur application comme insecticides, acaricides et fongicides |
-
1973
- 1973-11-20 DE DE2357930A patent/DE2357930A1/de not_active Withdrawn
-
1974
- 1974-10-29 US US05/518,837 patent/US3968232A/en not_active Expired - Lifetime
- 1974-11-15 BG BG28202A patent/BG21830A3/xx unknown
- 1974-11-15 SU SU2075502A patent/SU520013A3/ru active
- 1974-11-16 EG EG507A patent/EG11732A/xx active
- 1974-11-18 LU LU71304A patent/LU71304A1/xx unknown
- 1974-11-18 BR BR9633/74A patent/BR7409633A/pt unknown
- 1974-11-18 DD DD182427A patent/DD116000A5/xx unknown
- 1974-11-18 IL IL46076A patent/IL46076A/xx unknown
- 1974-11-18 CH CH1532274A patent/CH607885A5/xx not_active IP Right Cessation
- 1974-11-18 AT AT922374A patent/AT338045B/de not_active IP Right Cessation
- 1974-11-18 IT IT29565/74A patent/IT1044248B/it active
- 1974-11-18 BE BE150577A patent/BE822277A/xx unknown
- 1974-11-19 DK DK601474A patent/DK135804C/da not_active IP Right Cessation
- 1974-11-19 GB GB5002474A patent/GB1436519A/en not_active Expired
- 1974-11-19 ES ES432074A patent/ES432074A1/es not_active Expired
- 1974-11-19 PL PL1974175729A patent/PL91811B1/pl unknown
- 1974-11-19 IE IE2377/74A patent/IE41829B1/en unknown
- 1974-11-19 PH PH16531A patent/PH11681A/en unknown
- 1974-11-19 NL NL7415061A patent/NL7415061A/xx not_active Application Discontinuation
- 1974-11-19 TR TR18217A patent/TR18217A/xx unknown
- 1974-11-20 JP JP13282274A patent/JPS5726511B2/ja not_active Expired
- 1974-11-20 JP JP49132823A patent/JPS5761005B2/ja not_active Expired
- 1974-11-20 OA OA55346A patent/OA04801A/xx unknown
- 1974-11-20 FR FR7438140A patent/FR2251554B1/fr not_active Expired
-
1975
- 1975-10-30 ZA ZA00747396A patent/ZA747396B/xx unknown
-
1976
- 1976-11-09 KE KE2672A patent/KE2672A/xx unknown
-
1977
- 1977-12-30 MY MY54/77A patent/MY7700054A/xx unknown
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