GB1266462A - - Google Patents
Info
- Publication number
- GB1266462A GB1266462A GB1266462DA GB1266462A GB 1266462 A GB1266462 A GB 1266462A GB 1266462D A GB1266462D A GB 1266462DA GB 1266462 A GB1266462 A GB 1266462A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- chlorine
- fluorine
- compounds
- bromine
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 5
- 239000000460 chlorine Substances 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052731 fluorine Inorganic materials 0.000 abstract 5
- 239000011737 fluorine Substances 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000009435 amidation Effects 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 abstract 1
- RJBIAAZJODIFHR-UHFFFAOYSA-N dihydroxy-imino-sulfanyl-$l^{5}-phosphane Chemical class NP(O)(O)=S RJBIAAZJODIFHR-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
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
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2483—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-S (X = O, S, Se; n = 0, 1)
-
- 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
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2487—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-C(=X) (X = O, S, Se; n = 0, 1)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1,266,462. Phosphoroamidothioates. CHEVRON RESEARCH CO. 24 March, 1970 [25 March, 1969; 24 Feb., 1970], No. 14333/70. Heading C2P. The invention comprises compounds of Formula I where R is C 1-3 alkyl, R<SP>1</SP> is C 1-3 aliphatic hydrocarbyl, R<SP>2</SP> is hydrogen or C 1-3 alkyl, X is carbonyl or sulphonyl, Y is oxygen or sulphur and (a) when X is carbonyl, R<SP>3</SP> is hydrogen, C 1-18 alkyl, C 1-18 alkyl substituted by 1 to 4 fluorine, chlorine or bromine atoms, C 2-18 alkenyl, C 3-18 alkynyl, C 3-8 cycloalkyl, a heterocyclic radical containing 1 hetero atom (oxygen, sulphur or nitrogen) and 4 or 5 annular carbons, and a total of 4 to 8 carbons, C 2-12 alkoxyalkyl or alkylthioalkyl, C 1-12 alkoxy or alkylthio, phenyl, (optionally substituted by 1 or 2 C 1-3 alkyl or alkoxy groups, fluorine, chlorine or bromine atoms or nitro groups), styryl, phenylalkyl (C 1-3 alkyl), optionally substituted on the aromatic ring by fluorine, chlorine, bromine or nitro, phenoxyalkyl (C 13 alkyl), optionally substituted on the aromatic ring by fluorine, chlorine, bromine or nitro, thiophenoxyalkyl (C 13 alkyl) optionally substituted on the aromatic ring by fluorine, chlorine, bromine or nitro or C 1-3 mono-nitroalkyl or (b) when X is sulphonyl, R<SP>3</SP> is C 1-10 alkyl, C 3-8 cycloalkyl or phenyl, provided that when R is other than methyl, R<SP>1</SP> is methyl, R<SP>2</SP> is hydrogen, X is carbonyl and Y is oxygen, then R<SP>3</SP> is not phenyl, p-chlorophenyl or The compounds of Formula I, and compounds in which the above proviso does not apply may be prepared by various methods involving acylation of the amide group or amidation of a phosphorothiochloridate, and are used as pesticides either alone or as the active ingredients in conventional pesticidal compositions. 0,0 - Dialkyl - N - acylphosphoroamidothionates may be obtained by the reaction and may be converted to compounds of Formula I by reaction with R<SP>1</SP>#. S - Alkyl - S - aliphatic hydrocarbyl phosphorochloridoihioates may be obtained by the reaction sequence: S - Alkyl - S - aliphatic hydrocarbyl phosphoroamidothioates may be obtained from the chloridothioates by reaction with ammonia, and may be converted to compounds of Formula I by acylation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81038369A | 1969-03-25 | 1969-03-25 | |
| US1384670A | 1970-02-24 | 1970-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1266462A true GB1266462A (en) | 1972-03-08 |
Family
ID=26685327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1266462D Expired GB1266462A (en) | 1969-03-25 | 1970-03-24 |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5118502B1 (en) |
| AT (1) | AT301264B (en) |
| BE (1) | BE747646A (en) |
| CA (1) | CA926872A (en) |
| CH (2) | CH552631A (en) |
| DE (1) | DE2014027C3 (en) |
| DK (1) | DK130301B (en) |
| ES (1) | ES377885A1 (en) |
| FR (1) | FR2039679A5 (en) |
| GB (1) | GB1266462A (en) |
| IL (1) | IL34067A (en) |
| NL (1) | NL149181B (en) |
| SE (1) | SE369310B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL43144A (en) * | 1972-09-13 | 1977-02-28 | Ciba Geigy Ag | Thiophosphoric acid amide esters their preparation and their use in insecticidal acaricidal and nematicidal compositions |
| JPS604838B2 (en) * | 1976-09-20 | 1985-02-06 | 日本特殊農薬製造株式会社 | Organic phosphoric acid amide ester, its manufacturing process, and insecticide, acaricide, or nematocide |
| JPS604839B2 (en) * | 1976-09-20 | 1985-02-06 | 日本特殊農薬製造株式会社 | Organic phosphoric acid amide ester, its manufacturing process, and insecticide, acaricide, or nematocide |
| DE2702049A1 (en) * | 1977-01-19 | 1978-07-20 | Bayer Ag | SUBSTITUTED DITHIOPHOSPHONIC ACID ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
| DE2831934A1 (en) * | 1978-07-20 | 1980-02-07 | Bayer Ag | O-AETHYL-S-N-PROPYL-N-AMINOMETHYLIDEN-THIOLPHOSPHORIC ACID DIESTERIMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL |
| US4279897A (en) * | 1979-03-07 | 1981-07-21 | The Regents Of The University Of California | (Alkoxycarbonyl)(alkyl)aminosulfenyl derivatives of phosphoramidothioate esters |
| DE102007045955A1 (en) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Active agent combination, useful e.g. for combating animal pests and treating seeds of transgenic plants, comprises substituted amino-furan-2-one compound and at least one compound e.g. diazinon, isoxathion, carbofuran or aldicarb |
| EP2127522A1 (en) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Active-agent combinations with insecticidal and acaricidal properties |
-
1970
- 1970-03-09 CA CA076870A patent/CA926872A/en not_active Expired
- 1970-03-12 IL IL34067A patent/IL34067A/en unknown
- 1970-03-18 FR FR7009754A patent/FR2039679A5/fr not_active Expired
- 1970-03-19 BE BE747646D patent/BE747646A/en not_active IP Right Cessation
- 1970-03-20 NL NL707004055A patent/NL149181B/en not_active IP Right Cessation
- 1970-03-24 GB GB1266462D patent/GB1266462A/en not_active Expired
- 1970-03-24 ES ES377885A patent/ES377885A1/en not_active Expired
- 1970-03-24 DE DE2014027A patent/DE2014027C3/en not_active Expired
- 1970-03-24 DK DK150870AA patent/DK130301B/en not_active IP Right Cessation
- 1970-03-24 AT AT272670A patent/AT301264B/en not_active IP Right Cessation
- 1970-03-25 JP JP45025199A patent/JPS5118502B1/ja active Pending
- 1970-03-25 CH CH452570A patent/CH552631A/en not_active IP Right Cessation
- 1970-03-25 CH CH134773A patent/CH580639A5/xx not_active IP Right Cessation
- 1970-03-25 SE SE04122/70A patent/SE369310B/xx unknown
-
1974
- 1974-01-24 JP JP1058174A patent/JPS535654B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA926872A (en) | 1973-05-22 |
| CH552631A (en) | 1974-08-15 |
| IL34067A (en) | 1974-01-14 |
| CH580639A5 (en) | 1976-10-15 |
| NL149181B (en) | 1976-04-15 |
| JPS5118502B1 (en) | 1976-06-10 |
| DE2014027B2 (en) | 1974-11-28 |
| NL7004055A (en) | 1970-09-29 |
| AT301264B (en) | 1972-08-25 |
| FR2039679A5 (en) | 1971-01-15 |
| ES377885A1 (en) | 1972-10-16 |
| DK130301B (en) | 1975-02-03 |
| DE2014027A1 (en) | 1970-12-03 |
| SE369310B (en) | 1974-08-19 |
| IL34067A0 (en) | 1970-06-17 |
| JPS535654B1 (en) | 1978-03-01 |
| DK130301C (en) | 1975-06-30 |
| BE747646A (en) | 1970-08-31 |
| DE2014027C3 (en) | 1975-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |