GB1444684A – Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties
– Google Patents
GB1444684A – Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties
– Google Patents
Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties
Info
Publication number
GB1444684A
GB1444684A
GB463174A
GB463174A
GB1444684A
GB 1444684 A
GB1444684 A
GB 1444684A
GB 463174 A
GB463174 A
GB 463174A
GB 463174 A
GB463174 A
GB 463174A
GB 1444684 A
GB1444684 A
GB 1444684A
Authority
GB
United Kingdom
Prior art keywords
reacting
propargyl
esters
diethyl
dichloride
Prior art date
1973-02-09
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
Application number
GB463174A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SC Johnson and Son Inc
Original Assignee
SC Johnson and Son Inc
Priority date (The priority date 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 date listed.)
1973-02-09
Filing date
1974-01-31
Publication date
1976-08-04
1974-01-31
Application filed by SC Johnson and Son Inc
filed
Critical
SC Johnson and Son Inc
1976-08-04
Publication of GB1444684A
publication
Critical
patent/GB1444684A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
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
A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
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 System
C07F9/02—Phosphorus compounds
C07F9/28—Phosphorus compounds with one or more P—C bonds
C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
C07F9/40—Esters thereof
C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
C07F9/4078—Esters with unsaturated acyclic alcohols
Abstract
1444684 Unsaturated phosphonate diesters S C JOHNSON & SON Inc 31 Jan 1974 [9 Feb 1973] 4631/74 Heading C2P [Also in Division A5] Phosphonate diesters of the Formula (I) wherein R 1 is an alkyl or alkenyl radical having 2-12 carbon atoms or is cyclohexyl and R 2 is propargyl, C 1 -C 5 alkyl or 2-(2-butoxyethoxy)- ethyl, with the proviso that R 2 is propargyl when R 1 is cyclohexyl, are obtained (a) (when R 2 is propargyl) by reacting a dichloride R 1 P(O)Cl 2 (1 mole) with 2 mols. of propargyl alcohol in the presence of 2 equivalents of a base, e.g. triethylamine and suitably in the presence of a solvent, e.g. diethyl ether, or (b) (when R 2 is other than propargyl) by reacting the dichloride with one equivalent of alcohol (R 2 OH) and one equivalent of a base and suitably in a solvent and then reacting with one equivalent of propargyl alcohol and of the base. The products are useful as synergists for insecticides and the invention also includes as novel products the phosphonates of Formula I with the added proviso other than those in which R 1 is a C 2 -C 12 alkenyl radical. n-Butylphosphonic dichloride is obtained by reacting diethyl n-butyl phosphonate with PCl 5 at 105 C. for 6 hours. Diethyl n-butyl phosphonate is obtained by reacting n-butyl bromide with triethylphosphite under reflux conditions. Dialkylalkylphosphonates can also be obtained by reacting a dialkyl phosphite, e.g. diethyl phosphite, with sodium in a dry solvent, and then reacting with an alkyl halide, e.g. n-octyl bromide.
GB463174A
1973-02-09
1974-01-31
Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties
Expired
GB1444684A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US00331165A
US3856896A
(en)
1973-02-09
1973-02-09
Alkyl propargyl phosphonates
Publications (1)
Publication Number
Publication Date
GB1444684A
true
GB1444684A
(en)
1976-08-04
Family
ID=23292874
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB463174A
Expired
GB1444684A
(en)
1973-02-09
1974-01-31
Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties
Country Status (7)
Country
Link
US
(1)
US3856896A
(en)
JP
(1)
JPS49109540A
(en)
AU
(1)
AU6521574A
(en)
CA
(1)
CA1012548A
(en)
DE
(1)
DE2406783A1
(en)
FR
(1)
FR2217346B3
(en)
GB
(1)
GB1444684A
(en)
Families Citing this family (7)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
DE2727479A1
(en)
*
1977-06-18
1979-01-04
Bayer Ag
INSECTICIDES AND ACARICIDES
DE2853450A1
(en)
*
1978-12-11
1980-06-19
Basf Ag
THIONOPHOSPHONIC ACID ESTER
DE2936037A1
(en)
*
1979-09-06
1981-04-09
Bayer Ag, 5090 Leverkusen
PROPARGYL GROUP-CONTAINING METHANPHOSPHONIC ACID ESTERS AND THEIR USE IN SYNERGISTIC ACTIVE SUBSTANCE COMBINATIONS FOR PEST CONTROL
US4428945A
(en)
1980-11-21
1984-01-31
Rhone-Poulenc Agrochimie
O-Alkyl S-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides
US4472391A
(en)
*
1980-11-21
1984-09-18
Rhone-Poulenc Agrochimie
O-Aryl-s-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides
US4472390A
(en)
*
1980-12-31
1984-09-18
Rhone-Poulenc Agrochimie
S-Alkyls-(tertiary alkyl) alkylphosphonodithioate insecticides and nematocides
GB0211924D0
(en)
*
2002-05-23
2002-07-03
Syngenta Ltd
Composition
Family Cites Families (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3065125A
(en)
*
1960-01-28
1962-11-20
Monsanto Chemicals
Alkynyl phosphonothioates
US3071610A
(en)
*
1961-07-06
1963-01-01
Dow Chemical Co
O-[1-(chloromethyl)2-propynyl] o, o-dialkyl phosphates and phosphorothioates
US3803271A
(en)
*
1971-06-01
1974-04-09
Gaf Corp
Organophosphonates
1973
1973-02-09
US
US00331165A
patent/US3856896A/en
not_active
Expired – Lifetime
1974
1974-01-30
CA
CA191,312A
patent/CA1012548A/en
not_active
Expired
1974-01-31
GB
GB463174A
patent/GB1444684A/en
not_active
Expired
1974-02-05
AU
AU65215/74A
patent/AU6521574A/en
not_active
Expired
1974-02-08
FR
FR7404378A
patent/FR2217346B3/fr
not_active
Expired
1974-02-08
DE
DE19742406783
patent/DE2406783A1/en
active
Pending
1974-02-09
JP
JP49016731A
patent/JPS49109540A/ja
active
Pending
Also Published As
Publication number
Publication date
FR2217346A1
(en)
1974-09-06
FR2217346B3
(en)
1976-11-26
AU6521574A
(en)
1975-08-07
US3856896A
(en)
1974-12-24
CA1012548A
(en)
1977-06-21
DE2406783A1
(en)
1974-08-15
JPS49109540A
(en)
1974-10-18
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Legal Events
Date
Code
Title
Description
1976-12-15
PS
Patent sealed [section 19, patents act 1949]
1979-10-10
PCNP
Patent ceased through non-payment of renewal fee
