CA1224476A - N'-(methoxy)(methylthio)phosphinyl-n,n-dimethyl carbamimidothioic acid, ethyl ester - Google Patents
N'-(methoxy)(methylthio)phosphinyl-n,n-dimethyl carbamimidothioic acid, ethyl esterInfo
- Publication number
- CA1224476A CA1224476A CA000429715A CA429715A CA1224476A CA 1224476 A CA1224476 A CA 1224476A CA 000429715 A CA000429715 A CA 000429715A CA 429715 A CA429715 A CA 429715A CA 1224476 A CA1224476 A CA 1224476A
- Authority
- CA
- Canada
- Prior art keywords
- plants
- compound
- ethyl ester
- acid
- control
- 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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 68
- 241000238631 Hexapoda Species 0.000 abstract description 10
- 239000002917 insecticide Substances 0.000 abstract description 9
- 230000009885 systemic effect Effects 0.000 abstract description 8
- KDMOOUDVKGUQKQ-UHFFFAOYSA-N 3-[methoxy(methylsulfanyl)phosphoryl]-1,1-dimethylthiourea Chemical compound COP(=O)(SC)NC(=S)N(C)C KDMOOUDVKGUQKQ-UHFFFAOYSA-N 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 description 72
- 239000000203 mixture Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000006185 dispersion Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003440 toxic substance Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- 239000004094 surface-active agent Substances 0.000 description 19
- 231100000167 toxic agent Toxicity 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZSNFXARZPZJMTM-UHFFFAOYSA-N ethyl n,n-dimethylcarbamimidothioate Chemical compound CCSC(=N)N(C)C ZSNFXARZPZJMTM-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- 241000258937 Hemiptera Species 0.000 description 12
- -1 METHOXY(METHYLTHIO)PHOSPHINYL Chemical class 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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- 239000000370 acceptor Substances 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
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- 235000008504 concentrate Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- CBIBNFNHTLGLDZ-UHFFFAOYSA-N ethyl n'-dimethoxyphosphinothioyl-n,n-dimethylcarbamimidothioate Chemical compound CCSC(N(C)C)=NP(=S)(OC)OC CBIBNFNHTLGLDZ-UHFFFAOYSA-N 0.000 description 4
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- 125000004494 ethyl ester group Chemical group 0.000 description 3
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- 239000012433 hydrogen halide Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- NBAUXRCSDWYKRP-UHFFFAOYSA-N dimethyl phosphorochloridothioate Chemical compound COP(Cl)(=O)SC NBAUXRCSDWYKRP-UHFFFAOYSA-N 0.000 description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ZQGWBPQBZHMUFG-UHFFFAOYSA-N 1,1-dimethylthiourea Chemical compound CN(C)C(N)=S ZQGWBPQBZHMUFG-UHFFFAOYSA-N 0.000 description 1
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39910282A | 1982-07-16 | 1982-07-16 | |
| US399,102 | 1982-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1224476A true CA1224476A (en) | 1987-07-21 |
Family
ID=23578155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000429715A Expired CA1224476A (en) | 1982-07-16 | 1983-06-03 | N'-(methoxy)(methylthio)phosphinyl-n,n-dimethyl carbamimidothioic acid, ethyl ester |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4568670A (en:Method) |
| EP (1) | EP0099630A1 (en:Method) |
| JP (1) | JPS5920293A (en:Method) |
| AU (1) | AU553115B2 (en:Method) |
| BR (1) | BR8303003A (en:Method) |
| CA (1) | CA1224476A (en:Method) |
| DK (1) | DK254083A (en:Method) |
| GB (1) | GB2123832A (en:Method) |
| GR (1) | GR79310B (en:Method) |
| GT (1) | GT198302879A (en:Method) |
| IL (1) | IL68756A0 (en:Method) |
| NZ (1) | NZ204468A (en:Method) |
| PH (2) | PH18308A (en:Method) |
| ZA (1) | ZA834043B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL68757A (en) * | 1982-06-04 | 1987-12-20 | Dow Chemical Co | Phosphorus derivatives of carbamimidothioic acid esters and insecticidal compositions containing them |
| US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
| US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3825632A (en) * | 1969-12-15 | 1974-07-23 | Stauffer Chemical Co | Phosphorus-containing amidines |
| BE792901A (fr) * | 1971-12-17 | 1973-06-18 | Ciba Geigy | Amidines phosphorees et produits pesticides qui en contiennent |
| DE2831934A1 (de) * | 1978-07-20 | 1980-02-07 | Bayer Ag | O-aethyl-s-n-propyl-n-aminomethyliden-thiolphosphorsaeurediesterimide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| SU707232A1 (ru) * | 1978-08-14 | 1982-05-30 | Предприятие П/Я Р-6225 | Фосфорилированные триметилизотиомочевины, обладающие инсектоакарицидной активностью |
| IL68757A (en) * | 1982-06-04 | 1987-12-20 | Dow Chemical Co | Phosphorus derivatives of carbamimidothioic acid esters and insecticidal compositions containing them |
-
1983
- 1983-05-02 US US06/490,692 patent/US4568670A/en not_active Expired - Fee Related
- 1983-05-23 IL IL68756A patent/IL68756A0/xx unknown
- 1983-05-25 AU AU14975/83A patent/AU553115B2/en not_active Ceased
- 1983-06-01 EP EP83303160A patent/EP0099630A1/en not_active Withdrawn
- 1983-06-01 BR BR8303003A patent/BR8303003A/pt unknown
- 1983-06-01 GB GB08315035A patent/GB2123832A/en not_active Withdrawn
- 1983-06-03 CA CA000429715A patent/CA1224476A/en not_active Expired
- 1983-06-03 PH PH29010A patent/PH18308A/en unknown
- 1983-06-03 JP JP58099280A patent/JPS5920293A/ja active Pending
- 1983-06-03 ZA ZA834043A patent/ZA834043B/xx unknown
- 1983-06-03 NZ NZ204468A patent/NZ204468A/en unknown
- 1983-06-03 DK DK254083A patent/DK254083A/da not_active Application Discontinuation
- 1983-06-03 GR GR71567A patent/GR79310B/el unknown
- 1983-07-15 GT GT198302879A patent/GT198302879A/es unknown
-
1984
- 1984-10-29 PH PH31379A patent/PH19724A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU553115B2 (en) | 1986-07-03 |
| AU1497583A (en) | 1984-01-19 |
| PH18308A (en) | 1985-05-29 |
| GR79310B (en:Method) | 1984-10-22 |
| NZ204468A (en) | 1987-02-20 |
| IL68756A0 (en) | 1983-09-30 |
| GT198302879A (es) | 1985-01-05 |
| GB2123832A (en) | 1984-02-08 |
| GB8315035D0 (en) | 1983-07-06 |
| DK254083A (da) | 1984-01-17 |
| ZA834043B (en) | 1985-01-30 |
| BR8303003A (pt) | 1984-04-17 |
| US4568670A (en) | 1986-02-04 |
| PH19724A (en) | 1986-06-17 |
| EP0099630A1 (en) | 1984-02-01 |
| DK254083D0 (da) | 1983-06-03 |
| JPS5920293A (ja) | 1984-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |