GB955754A - New unsaturated organophosphorus esters - Google Patents
New unsaturated organophosphorus estersInfo
- Publication number
- GB955754A GB955754A GB530262A GB530262A GB955754A GB 955754 A GB955754 A GB 955754A GB 530262 A GB530262 A GB 530262A GB 530262 A GB530262 A GB 530262A GB 955754 A GB955754 A GB 955754A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- groups
- carbon atoms
- represent
- compounds
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- -1 phosphorus compound Chemical class 0.000 abstract 14
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 6
- 239000001301 oxygen Substances 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- 239000002689 soil Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 abstract 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 241000244206 Nematoda Species 0.000 abstract 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 1
- 241001163248 Schoenocaulon officinale Species 0.000 abstract 1
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 abstract 1
- 240000004460 Tanacetum coccineum Species 0.000 abstract 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000006378 damage Effects 0.000 abstract 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 239000005556 hormone Substances 0.000 abstract 1
- 229940088597 hormone Drugs 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 229940059904 light mineral oil Drugs 0.000 abstract 1
- BUYMVQAILCEWRR-UHFFFAOYSA-N naled Chemical compound COP(=O)(OC)OC(Br)C(Cl)(Cl)Br BUYMVQAILCEWRR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 229940015367 pyrethrum Drugs 0.000 abstract 1
- 229940080817 rotenone Drugs 0.000 abstract 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6578—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/327—Esters with unsaturated acyclic alcohols
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or 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
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4434—Amides thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4442—Esters with unsaturated acyclic alcohols
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
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- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (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
The invention comprises a phosphorus compound having the general formula: <FORM:0955754/C2/1> wherein R, R1 and R2 each represent a substituted or unsubstituted hydrocarbon group, R3 is hydrogen or a group represented by R, m, n, p and q each is 0 or 1, and X and Y each represent an oxygen or sulphur atom or the group NH or NR0 wherein R0 is a group represented by R, with the proviso that when m and n are each 1 and X and Y each represent an oxygen or sulphur atom, R and R1 may be linked together to form a divalent group, and that when either or both of X and Y represent the group NR0 the groups R and R0, or R1 and R0, may be linked together to form a divalent group. The groups R, R1, R2, R3 and R0 may be aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon groups, e.g. alkyl, cycloalkyl, phenyl, naphthyl, aralkyl or alkaryl groups. When the hydrocarbon groups are substituted the preferred substituents are halogen, preferably bromine or chlorine, the nitro group, cyano group or a group of the formula: -N(R)w-(H)v wherein R is as defined above, v is 0, 1 or 2 and v+w=2, an aliphatic oxycarbonyl group, e.g. a carboalkoxy or carboalkoxy-alkylene group of up to 8 carbon atoms, an RO-group, or an amido group including the grouping NHC(O)R, wherein R is as defined above. When R and R1 form a divalent group the latter is preferably an alkylene group of up to 10 carbon atoms having a chain of 1 to 5, preferably 2 to 3, carbon atoms linked to X and Y and when R and R0 or R1 and R0 form a divalent group the latter is preferably an alkylene group of up to 10 carbon atoms with 4 or 5 carbon atoms in the chain thereof which is bonded with its ends to the nitrogen atom, thus the divalent chain may form with the nitrogen atom a piperidino group. Preferred compounds are those in which m and n in the general formula are each 1, X and Y represent oxygen, both R and R1 are C1-C4 alkyl groups, and R3 is hydrogen. Examples of suitable substituted hydrocarbon groups are haloalkyl groups, nitroalkyl groups, haloaryl groups, and amino-substituted groups, e.g. 2-aminoethyl, 2-diethylaminoethyl, the aniline group, p-dimethylaminophenyl and p-ethylaminobenzyl. The thiovinyl compounds, i.e. those in which p and q are zero, may be obtained by reacting a compound of the formula: <FORM:0955754/C2/2> wherein alkyl is an alkyl group preferably an unbranched C1-C4 alkyl group, with an ester of an alpha-halothioacetic acid of the formula hal.CH(R3). CO.SR2 wherein hal is halogen, e.g. Br or Cl. The sulphinylvinyl and the sulphonylvinyl compounds, i.e. those in which either or both of p and q are 1 may be obtained by oxidising the thiovinyl compounds (in which p and q are zero). The reaction to form the thiovinyl compounds is preferably effected at from 40 DEG C. to 150 DEG C. and it is preferred to use an excess of the phosphorus compound. The oxidation of the thiovinyl compounds to form the sulphinylvinyl and the sulphonylvinyl compounds is preferably effected in a controlled manner by means of a per acid, e.g. peracetic or monoperphthalic acid, and a polthaloalkane, e.g. chloroform, may be present as solvent. Suitable temperatures are from 10 DEG to 40 DEG C. The products have pesticidal properties (see Division A5). The alpha-halothiolacetic acids of the formula hal. CH(R3).CO.SR2 may be obtained by reacting a haloacetyl halide with an aqueous solution of an alkali metal salt of the appropriate mercaptan and an example is given for the production of S-phenyl chlorothiolacetate by reacting chloroacetyl chloride with thiophenol in the presence of sodium hydroxide and water.ALSO:A pesticidal composition contains as active ingredient a phosphorus compound of the general formula: <FORM:0955754/A5-A6/1> wherein R, R1 and R2 each represent a substituted or unsubstituted hydrocarbon group, R3 is hydrogen or a group represented by R, m, n, p and q each is 0 or 1, and X and Y each represent an oxygen or sulphur atom or the group NH or NR DEG wherein R DEG is a group represented by R, with the proviso that when m and n are each 1 and X and Y each represent an oxygen or sulphur atom, R and R1 may be linked together to form a divalent group, and that when either or both of X and Y represent the group NR DEG the groups R and R DEG , or R1 and R DEG , may be linked together to form a divalent group. The groups R, R1, R2, R3 and R DEG may be aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic hydrocarbon groups, e.g. alkyl, cycloalkyl, phenyl, naphthyl, aralkyl or alkaryl groups. When the hydrocarbon groups are substituted the preferred substituents are halogen, preferably bromine or chlorine, the nitro group, cyano group or a group of the formula -N(R)w-(H)v wherein R is as defined above, v is 0, 1 or 2, and v + w = 2, an aliphatic oxycarbonyl group, e.g. a carboalkoxy or carboalkoxy-alkylene group of up to 8 carbon atoms, an RO-group, or an amido group including the grouping NHC(O)R, wherein R is as defined above. When R and R1 form a divalent group the latter is preferably an alkylene group of up to 10 carbon atoms having a chain of 1 to 5, preferably 2 to 3, carbon atoms linked to X and Y and when R and R DEG or R1 and R DEG form a divalent group the latter is preferably an alkylene group of up to 10 carbon atoms with 4 or 5 carbon atoms in the chain thereof which is bonded with its ends to the nitrogen atom, thus the divalent chain may form with the nitrogen atom a piperidino group. Preferred compounds are those in which m and n in the general formula are each 1, X and Y represent oxygen, both R and R1 are C1-C4 alkyl groups, and R3 is hydrogen. The composition may be in the form of a solution or dispersion and a carrier and/or surface active or spreading agent may be present. The carrier may be a finely divided solid or may be water, acetone, or a light mineral oil, e.g. kerosene. The composition may also be in a form suitable for use as an aerosol. Other insecticides may be present, e.g. pyrethrum, rotenone, sabadilla, DDT, benzene hexachloride, thiodiphenylamine, cyanides, tetraethyl pyrophosphate, diethyl p-nitrophenyl thiophosphate, dimethyl 2,2-dichlorovinyl phosphate, 1, 2-dibromo - 2,2 - dichloroethyl dimethyl phosphate, azobenzene and compounds of lead, arsenic and/or fluorine. Hormones and fertilizers may also be present. The active ingredient may also be used for the destruction of nematodes and fungi in soil by intimately disseminating it in the soil.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US88674A US3069313A (en) | 1961-02-13 | 1961-02-13 | Organophosphorus compounds |
US144526A US3151147A (en) | 1961-10-12 | 1961-10-12 | Omicron, omicron-dialkyl omicron-1-sulfonylvinyl and omicron, omicron-dialkyl omicron-1-sulfinylvinyl phosphates |
Publications (1)
Publication Number | Publication Date |
---|---|
GB955754A true GB955754A (en) | 1964-04-22 |
Family
ID=26778935
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB530262A Expired GB955754A (en) | 1961-02-13 | 1962-02-12 | New unsaturated organophosphorus esters |
Country Status (3)
Country | Link |
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BE (1) | BE613830A (en) |
GB (1) | GB955754A (en) |
NL (1) | NL274751A (en) |
-
0
- NL NL274751D patent/NL274751A/xx unknown
- BE BE613830D patent/BE613830A/xx unknown
-
1962
- 1962-02-12 GB GB530262A patent/GB955754A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NL274751A (en) | |
BE613830A (en) |
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