US3035079A - New organic phosphorus compounds and their manufacture and use - Google Patents
New organic phosphorus compounds and their manufacture and use Download PDFInfo
- Publication number
- US3035079A US3035079A US691163A US69116357A US3035079A US 3035079 A US3035079 A US 3035079A US 691163 A US691163 A US 691163A US 69116357 A US69116357 A US 69116357A US 3035079 A US3035079 A US 3035079A
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- parts
- radical
- compounds
- acetone
- residue
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- 150000002903 organophosphorus compounds Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
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- 239000003921 oil Substances 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
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- 239000000203 mixture Substances 0.000 description 20
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- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 238000009835 boiling Methods 0.000 description 13
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
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- 241000238814 Orthoptera Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- 235000010749 Vicia faba Nutrition 0.000 description 2
- 235000002098 Vicia faba var. major Nutrition 0.000 description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 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 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
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- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
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- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- WUFFGJVXZCDALE-UHFFFAOYSA-N 2-ethoxy-1,3,2-dioxaphospholane Chemical compound CCOP1OCCO1 WUFFGJVXZCDALE-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
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- 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
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- 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
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
-
- 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
-
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- 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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- 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
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- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- 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
Definitions
- This invention provides new organic phosphorus compounds of the general formula in which R, R and R represent alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residues which may contain substituents, and of which R and R may together form part of a ring system, R represents hydrogen or an alkyl residue or a halogen atom, R represents an alicyclic, aromatic or heterocyclic residue, X and Y represent -O, S, NH- or ITT R and Z represents oxygen or sulfur, and n and m each represent the whole number 1 or 2 or compounds of the general formula in which R, R R R R X, Y, Z and n and m have the meanings given above.
- the condensation product of a:a-dichlorobenzoylacetic acid ethyl ester with trimethyl phosphite can be given the following formulae CH3-O
- the invention therefore includes compounds of the above Formulae I and II and also any mixtures of these compounds, since the isomerism of the compounds can be considered as keto-enol tautomerisms. Accordingly, when one form is given in this specification it is to be understood that the other form is included, provided that that form is capable of existing.
- the new compounds are valuable agents for combating pests, especially animal pests. They are active against the various stages of development, such as eggs, larvae and imagines, so that they are both contact and stomach poisons. Suitably substituted compounds of this invention exhibit an inner-therapeutic, so-called systemic, action when applied to plants. Especially valuable are compounds of the general formulae in which R, R and R represent lower alkyl residues containing l-4 carbon atoms, R represents a hydrogen atom or a chlorine atom, and R represents a cyclohexyl, phenyl, furyl or tetrahydrofuryl residue which may contain substituents.
- the compounds of the general formula P-ZR Ri-(Y)m-i which may be used as starting materials are derivatives of trivalent phosphorus, whereas the products of the invention are derivatives of pentavalent phosphorus.
- the aliphatic residues which the symbols R and R may represent, may have straight or branched chains and may be saturated or unsaturated. They may be substituted or unsubstituted. There may be mentioned, for example, methyl, ethyl, propyl, isopropyl, butyl, hexyl, 2- ethylbutyl, octyl, 2-butyloctyl, dodecyl, octadecyl, allyl and 2-chloroethyl groups, and also radicals containing thiocyano, cyano or ester groups.
- the residues R and R may be identical or different from one another.
- R is advantageously a lower alkyl residue containing 1-4 carbon atoms.
- Trimethylphosphite triethylphosphite, tripropylphosphite, diethyl-dodecylphosphite, tri-(2-chlorethyl)-phosphite and the ester of the formula CHr-O P-O C2115 GHQ-O
- the aromatic radicals, which R and R may represent may be mononuclear or polynuclear, and may contain nuclear substituents. There may 'be mentioned, for example, phenyl, 2- or 4-chlorophenyl, 2:4-dich1orophenyl, 4-methoxyphenyl, 4-nitrophenyl, naphthyl and 4-diphenyl groups.
- compounds such as 2:4-dichlorophenyl .diethylphosphite and 4-ch1orophenyl dimethyl phosphite may be mentioned.
- compounds in which one or two residues are bound directly by a carbon atom to the phosphorus atom for example, phenyl-phosphorous acid diethyl ester of the formula 021150
- araliphatic radicals which R and R may represent, there may be mentioned the benzyl radical, among the cycloaliphatic radicals the cyclohexyl radical, and among the heterocyclic radicals the tetrahydrofurfuryl radical.
- Starting materials containing such radicals are, for example, cyclohexyl diethylphosphite, tetrahydrofurfuryl dimethylphosphite and dibenzylpropylphosphite.
- triethylthiophosphite of the formula CaHsS cz as and among those in which X and Y represent nitrogen, the compound of the formula 4
- the compounds of the general formula PMe 1( )m-1 Z are salts of disubstituted phosphites or phosphinic acids for example, sodium salts of dimethylphosphite, diethylphosphite, dodecylethylphosphite, cyclohexylrnethylphoe phite, tetrahydrofurfurylethylphosphite or benzyl ethyl phosphite.
- the compounds of the general formula P-Hal R1( m-l Z are phosphoric acid monohalides, for example, phosphoric acid diethylester monochloride, thiophosphoric acid diethylester monochloride or bis-(dimethylamido)-phosphoric acid monochloride.
- the compounds of the general formula are esters of halogenated acylacetic acids derived from alicyclic aromatic or heterocyclic carboxylic acids advantageously benzoyl-, hexahydrobenzoyl-, furoylor tetrahydrofuroylacetic acid.
- the residue R may have the meanings given above for the residues R and R Advantageously it consists of a lower alkyl group containing 1-4 carbon atoms.
- the residue R may be a halogen atom, advantageously a chlorine atom, or a hydrogen atom or an alkyl residue advantageously containing l-4 carbon atoms, such as the methyl group.
- R may be a heterocyclic residue, such as the furyl residue or tetrahydrofuryl residue, an aryl residue, for example, the phenyl, chlorophenyl, nitrophenyl group, or a cycloalkyl residue, such as the cyclohexyl group.
- reaction components are heated together at a raised temperature, for example, within the range of 50-200 C., and advantageously about 150 C. It may be of advantage or convenient to work in an inert solvent, such as benzene, toluene, xylene, chlorobenzene or benzine and, if desired in an atmosphere of an inert gas, for example, under nitrogen, and/ or under reduced pressure.
- an inert solvent such as benzene, toluene, xylene, chlorobenzene or benzine and, if desired in an atmosphere of an inert gas, for example, under nitrogen, and/ or under reduced pressure.
- the products of this invention are valuable agents for combating pests
- the invention also provides preparations for combating pests, which contain a product of the invention as active substance, and a process for combating pests With such preparations.
- R, R and R represent alkyl residues containing l-4 carbon atoms
- R represents a hydrogen atom or a chlorine atom
- R represents a cyclohexyl, phenyl, furyl or tetrahydrofuryl group which may contain substituents.
- a very Wide variety of materials can be protected against pests, and gaseous, liquids or solid materials may be used as carriers for the active substances.
- materials to be protected or to be used as carriers there may be mentioned, for example, air, especially in rooms, and liquids, for example, water in ponds, and any non-living or living solid substratum, for example, any objects in living rooms, in cellars, in plaster, floors, stables, and also pelts, feathers, wool or the like, and living organisms of the vegetable and animal kingdom at all stages of development, so far as they are not sensitive to the pest combating agent.
- the compounds are used for combating pests by the usual methods, for example, by treating the material to be protected with the compound in the formula of vapour, for example, in the form of a fumigating preparation or in the form of a dusting powder or spraying liquor, for example, in the form of a solution or suspension, which may be prepared with water or a suitable organic solvent, for example, alcohol, petroleum, tar distillates or the like.
- Aqueous solutions of the active substances or aqueous emulsions of organic solvents containing the active substances may be used or coating, spraying or immersing the objects to be protected.
- the spraying preparations or dusting powders may contain the usual inert fillers or identifying agents, for example, kaolin, gypsum or bentonite or other additions, such as sulfite cellulose waste liquor, cellulose derivatives or the like, and also the usual wetting agents or adherent agents for improving the wetting capacity and adherence of the preparations.
- the pest combating preparations may be made up in powdered form or in the form of aqueous dispersions or pastes or as self-dispersing oils.
- the preparations may contain compounds of the invention as the sole active substances or in admixture with other insecticides and/or fungicides. Such preparations may he used for the protection of plants by the usual spraying, pouring, dusting or fumigating methods.
- Example 1 A solution of 13.05 parts of uza-dichlorobenzoyl-acetic acid ethyl ester (boiling at 110 C. under 0.008 mm. pressure) in 15 parts by volume of chlorobenzene is heated to the boil. 6.8 parts of trimethyl phosphite are added dropwise in the course of 5 minutes, and the reaction is completed by boiling the mixture for one hour under reflux. 2.1 parts of methyl chloride are collected. By evaporating the volatile constituents at 95 C. under reduced pressure produced by a water jet pump there is obtained as residue 15.9 parts of a bright yellow oil, which dissolves well in acetone and alcohol and scarcely dissolves at all in water.
- Example 2 A solution of 13.05 parts of am-dichlorobenzoyl-acetic acid ethyl ester in 15 parts by volume of chlorobenzene is heated to the boil and 9.1 parts of triethylphosphite are added dropwise in the course of 5 minutes. The initially vigorous evolution of ethyl chloride is completed by boiling for one hour under reflux. The solvent and the excess of triethyl phosphite are removed in vacuo at 95 C. The residue (18.8 parts) is an oily liquid which boils at 168 C. under 0.3 mm. of mercury.
- Example 3 A solution of 12.35 parts of azu-dichlorobenzoyl-acetic acid methyl ester (boiling at IOU-102 C. under 0.2 mm. pressure) in 13 parts by volume of chlorobenzene is heated to the boil and 6.8 parts of trimethyl phosphite are added dropwise in the course of 5 minutes. In order to complete the reaction the mixture is maintained at the boil for a further hour. The volatile constituents are then removed in vacuo at 95 C., and there is obtained a residue consisting of 16.7 parts of a very mobile oil, which dissolves in acetone and isopropyl alcohol, and which boils at 154-158 C. under 0.04 mm. pressure.
- Example 4 To a mixture of 12.35 parts of aza-dichlorobenzoylacetic acid methyl ester and 13 parts by volume of chlorobenzene at the boiling temperature there are added dropwise 9.1 parts of triethyl phosphite. When the addition is complete, the solution is maintained at the boil for a further hour. The solvent and volatile constituents are then removed in vacuo at a bath temperature of C. There is obtained as residue a bright yellow oil, which is soluble in acetone and isopropyl alcohol.
- Example 5 A mixture of 14.07 parts of am-dichloro-para-chlorobenzoyl-acetic acid methyl ester (boiling at 121129 C. under 0.2 mm. pressure) and 15 parts by volume of chlorobenzene is mixed dropwise at the boil with 6.82 parts of trimethyl phosphite. When the dropwise addition of the trimethyl phosphite is complete, the solution is maintained at the boil for a further hour. At the end of this period 2.4 parts of methyl chloride will have been collected in the receiver cooled with Dry Ice and acetone. The volatile constituents are removed in vacuo, and there are obtained as residue 18.4 parts of a thickly liquid oil, which is easily soluble in acetone and isopropyl alcohol.
- Example 6 14.07 parts of a-monochloro-ortho-chlorobenZoyl-acetic acid methyl ester in 16 parts by volume of chlorobenzene are heated to the boil. 6.8 parts of trimethyl phosphite are added dropwise, and the reaction is completed by boiling the mixture for a further /2 hour. After distilling oil the volatile constituents in vacuo, there are obtained 16.9 parts of a poorly mobile oil, which is soluble in acetone and isopropyl alcohol.
- Example 7 12.87 parts of a-chloro-para-nitrobenzoyl-acetic acid methyl ester (melting at 106107 C.) and 13 parts by volume of chlorobenzene are heated to the boil, and 6.8 parts of trimethyl phosphite are added dropwise. The mixture is boiled under reflux for a further hour to complete the reaction. The volatile constituents are then removed in vacuo at a bath temperature of 95 C. 'The residue is a yellow oil (16.85 parts) which is easily soluble in isopropyl alcohol and acetone.
- Example 8 7.45 parts of triethyl phosphite are added in the course of 5 minutes to a mixture of 10.5 parts of a-chloro-paranitrobenzoyl-acetic acid methyl ester and 12 parts by volume of chlorobenzene maintained at the boil. When the addition is complete, the reaction mixture is boiled under reflux for a further hour, and then the solvent and excess of phosphite are removed in vacuo at a bath temperature of 95 C. The residue is a yellow oil (14.8 parts), which dissolves well in alcohol and acetone.
- Example 9 12.55 parts of aza-dichlorofuroyl-acetic acid ethyl ester are diluted with 15 parts by volume of chlorobenzene. The mixture is brought to the boil, and 6.8 parts of trimethylphosphite are added. After boiling the mixture under reflux for /2 hour 2.2 parts of methyl chloride are collected. The volatile constituents are removed at 95% C. under the reduced pressure of a water jet pump, and the residue consists of 14.1 parts of a very mobile oil, which dissolves in acetone and isopropyl alcohol.
- Example 10 A solution of 12.6 parts of aza-dichloro-hexahydrobenzoyl-acetic acid methyl ester (boiling at 102-103 C.
- Example 11 7 dropWise in the course of 5 minutes.
- the mixture is mainl3.05 parts of dichlorobenzoyl-acetic acid ethyl ester in 15 parts by volume of xylene are heated to the boil, and 12.2 parts of diethyl allyl phosphite tained fora further hour at 180 C. 2 parts of ethyl chloride are collected.
- the volatile constituents are removed in vacuo at C., and the residue consists of 20.8 parts of an easily mobile oil, which dissolves well in (boiling at 6466 C. under 12 mm. pressure) are added 75 alcohol and acetone.
- ozn or oorn (boiling at 49 C. under mm. pressure) are added dropwise.
- the mixture is slowly heated to 215 C. and maintained at that temperature for a further hour.
- 0.9 part of ethyl chloride is collected.
- the reaction does not take place solely with the splitting off of ethyl chloride, but partially involves splitting up of the ethylene phosphite ring.
- the easily volatile constituents are removed in vacuo at 180 C., and the residue is an easily mobile oil (17.8 parts), which dissolves well in alcohol and acetone and hardly at all in water.
- Example 14 9.9 parts of phenyl-phosphonous acid diethyl ester (boiling at 108114 C. under 10 mm. pressure) are added dropwise to a mixture of 13.05 parts of dichlorobenzoyl-acetic acid ethyl ester with 15 parts by volume of chlorobenzene, the mixture being heated to the boil. The reaction is finished in the course of hour, and 2.0 parts of ethyl chloride are collected. After removing the xylene in vacuo there are obtained 19.3 parts of a thinly liquid oil which dissolves well in alcohol and acetone.
- Example 16 21.4 parts of the sodium salt of benzoyl-acetic acid ethyl ester are stirred well in 50 parts by volume of chlorobenzene. Beginning at 20 C. 189 parts of diethyl thiophosphoric acid ester chloride are added dropwise in the course of 20 minutes while stirring, the temperature being raised to 30 C. The mixture is allowed to react completely overnight at 50-60 C. After being cooled, the solution is washed three times with a small amount of water, dried over sodium sulfate, and then the solvent it is removed in vacuo. The residue consists of 25.8 parts of a mobile oil, which dissolves well in alcohol and acetone.
- Example 17 2 parts of the condensation product obtained as described in Example 1 or 2 are mixed with 1 part of the condensation product of 1 mol of tertiary octyl phenol and 8 mols of ethylene oxide, and 7 parts of isopropanol.
- Example 1 Example 2 For each plant a mark is used. means that no living aphids are present, means a good action, only a few aphids alive, and means an insufficient or no action.
- Example 1 Spray liquor Action of concentration, aphids percent Example 1 (C)
- leaves were immersed in spray liquors containing 0.04% of the active substance. When dry the leaves were fed to locusts.
- the compounds of Examples 1 and 2 also exhibit a good action against the eggs of Ephestia kiihniella. They may be used in dormant spray preparations as active substances against the wintering stages of pests.
- wetting and emulsifying agents there may be used wetting and emulsifying agents other than those mentioned above.
- non-ionic products for example, condensation products of aliphatic alcohols, amines or carboxylic acids containing a long-chain hydrocarbon radical of about l030 carbon atoms with ethylene oxide, such as the condensation product of octadecyl alcohol with 25-30 mols of ethylene oxide, or the condensation products of soya bean fatty acid with 30 mols of ethylene oxide, or that of commercial oleylamine with 15 mols of ethylene oxide, or that of dodecyl mercaptan with 12 mols of ethylene oxide.
- condensation products of aliphatic alcohols, amines or carboxylic acids containing a long-chain hydrocarbon radical of about l030 carbon atoms with ethylene oxide such as the condensation product of octadecyl alcohol with 25-30 mols of ethylene oxide, or the condensation products of soya bean fatty
- anion-active emulsifying agents which may be used, there may be mentioned the sodium salt of dodecyl alcohol sulfonic acid ester, the sodium salt of dodecylbenzene sulfonic acid, the potassium or triethanolarnine salt of oleic acid or abietic acid, or a mixture of these acids, or the sodium salt of a petroleum sulfonic acid.
- isopropanol there may be used other solvents for making up the spray concentrates, for example, ethyl alcohol, methanol, butanol, acetone, methyl ethyl ketone, methyl-cyclohexanol, benzene, toluene, xylene, kerosene or petroleum fractions. There may, of course, be used mixtures of these solvents.
- Example 18 2 parts of the product of Example 2 are mixed with 9 parts of chalk and 1 part of a wetting agent. There is obtained a spray powder, which can be used for making spray liquors by suspending it in water. By treating the walls of stables with such a spray liquor containing 0.4% of active substance, good results are obtained against flies and gnats.
- Example 19 1 part of the product of Example 2. is mixed with 99 parts of tale.
- the resulting mixture is an insecticidal dusting powder, which is suitable for dusting vines to combat Pyralis caterpillars and Conchylis caterpillars.
- the talcum may be replaced wholly or in part by sulfur, in which case the preparation is also active against Oidium.
- other pulverulent carriers may be used, such as chalk, bentonite, kaolin or mixtures thereof.
- R and R is each selected from the group consisting of an alkyl radical containing at most 18 carbon atoms, an allyl radical, a tetrahydrofurfuryl radical, a benzyl radical, a phenyl radical and a chlorophenyl radical;
- R represents an alkyl radical containing at most 18 carbon atoms;
- R represents a member selected from the group consisting of a chlorine atom and a bromine atom;
- R represents a member selected from the group consisting of a phenyl radical, a chlorophenyl radical, a cyclohexyl radical, a furyl radical, a benzene radical which is substituted by a lower alkyl radical, a benzene radical which is substituted by a lower alkoxy radical, a benzene radical which is substituted by a nitro group and a benzene radical which is substituted by a nitro group and
- R and R is each selected from the group consisting of an alkyl radical containing at most 18 carbon atoms, an allyl radical, a tetrahydrofurfuryl radical, a benzyl radical, a phenyl radical and a chlorophenyl radical;
- R represents an alkyl radical containing at most 18 carbon atoms;
- R represents a member selected from the group consisting of a chlorine atom and a bromine atom;
- R represents a member selected from the group consisting of a phenyl radical, a chlorophenyl radical, a cyclohexyl radical, a furyl radical, a benzene radical which is substituted by a lower alkyl radical, a benzene radical which is substituted by a lower alkoxy radical, a benzene radical which is substituted by
- R represents a lower alkyl radical
- Y represents an oxygen atom
- m and 12 each represents an integer of at most 2
- Z represents a member selected from the group consisting of an oxygen atom and a sulfur atom; in admixture with an insecticidally inactive carrier.
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- 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)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH875583X | 1956-10-25 |
Publications (1)
Publication Number | Publication Date |
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US3035079A true US3035079A (en) | 1962-05-15 |
Family
ID=4544366
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US691163A Expired - Lifetime US3035079A (en) | 1956-10-25 | 1957-10-21 | New organic phosphorus compounds and their manufacture and use |
Country Status (7)
Country | Link |
---|---|
US (1) | US3035079A (de) |
BE (1) | BE563003A (de) |
CH (1) | CH353007A (de) |
DE (1) | DE1197271B (de) |
FR (1) | FR1190017A (de) |
GB (1) | GB875583A (de) |
NL (1) | NL222265A (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3134775A (en) * | 1957-10-25 | 1964-05-26 | Ici Ltd | New pesticidal triazine derivatives |
US3136690A (en) * | 1959-10-12 | 1964-06-09 | Ciba Ltd | Methods and compositions for combating pests with beta-phosphate esters of -2-butenoates of mono glyceriate heterocyclic acetals and glyceriate carbonates |
US4088758A (en) * | 1975-08-20 | 1978-05-09 | Bayer Aktiengesellschaft | O-(1-Phenyl-2-carbalkoxy-vinyl)-thionophosphoric (phosphonic) acid esters and ester-amides and method for combatting insects |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1155437B (de) * | 1959-04-07 | 1963-10-10 | Dr Friedrich Cramer | Verfahren zur Herstellung von Phospho-enolbrenztraubensaeuredibenzylester |
BE595900A (de) * | 1959-10-12 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT167432B (de) * | 1946-10-12 | 1951-01-10 | Bertha Braendli-Schafroth | Schädlingsbekämpfungsmittel |
US2668174A (en) * | 1950-08-15 | 1954-02-02 | Celanese Corp | Monopropyl dixylyl phosphate and process |
US2678329A (en) * | 1950-11-06 | 1954-05-11 | Monsanto Chemicals | Dialkyl monoaryl esters of orthophosphoric acid |
US2685552A (en) * | 1952-02-29 | 1954-08-03 | Shell Dev | Dimethyl 1-carbomethoxy-1-propen-2-yl phosphate |
CA523521A (en) * | 1956-04-03 | R. Whetstone Richard | Complex arylphosphonates | |
US2766260A (en) * | 1953-10-09 | 1956-10-09 | Gen Aniline & Film Corp | Methine dyestuff intermediates |
US2864828A (en) * | 1957-06-11 | 1958-12-16 | Charles R Russell | Esters of gamma-(tetrahydro-2-furyl) alkanols |
US2894018A (en) * | 1957-07-16 | 1959-07-07 | Bayer Ag | Di(lower alkyl)-mono(alpha-phenyl-beta-carbalkoxy-vinyl) phosphate esters |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE974569C (de) * | 1951-09-25 | 1961-03-02 | Ciba Geigy | Schaedlingsbekaempfungsmittel |
-
0
- BE BE563003D patent/BE563003A/xx unknown
- NL NL222265D patent/NL222265A/xx unknown
-
1956
- 1956-10-25 CH CH353007D patent/CH353007A/de unknown
-
1957
- 1957-10-17 DE DEC15639A patent/DE1197271B/de active Pending
- 1957-10-21 US US691163A patent/US3035079A/en not_active Expired - Lifetime
- 1957-10-21 GB GB32839/57A patent/GB875583A/en not_active Expired
- 1957-10-23 FR FR1190017D patent/FR1190017A/fr not_active Expired
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA523521A (en) * | 1956-04-03 | R. Whetstone Richard | Complex arylphosphonates | |
AT167432B (de) * | 1946-10-12 | 1951-01-10 | Bertha Braendli-Schafroth | Schädlingsbekämpfungsmittel |
US2668174A (en) * | 1950-08-15 | 1954-02-02 | Celanese Corp | Monopropyl dixylyl phosphate and process |
US2678329A (en) * | 1950-11-06 | 1954-05-11 | Monsanto Chemicals | Dialkyl monoaryl esters of orthophosphoric acid |
US2685552A (en) * | 1952-02-29 | 1954-08-03 | Shell Dev | Dimethyl 1-carbomethoxy-1-propen-2-yl phosphate |
US2766260A (en) * | 1953-10-09 | 1956-10-09 | Gen Aniline & Film Corp | Methine dyestuff intermediates |
US2864828A (en) * | 1957-06-11 | 1958-12-16 | Charles R Russell | Esters of gamma-(tetrahydro-2-furyl) alkanols |
US2894018A (en) * | 1957-07-16 | 1959-07-07 | Bayer Ag | Di(lower alkyl)-mono(alpha-phenyl-beta-carbalkoxy-vinyl) phosphate esters |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3134775A (en) * | 1957-10-25 | 1964-05-26 | Ici Ltd | New pesticidal triazine derivatives |
US3136690A (en) * | 1959-10-12 | 1964-06-09 | Ciba Ltd | Methods and compositions for combating pests with beta-phosphate esters of -2-butenoates of mono glyceriate heterocyclic acetals and glyceriate carbonates |
US4088758A (en) * | 1975-08-20 | 1978-05-09 | Bayer Aktiengesellschaft | O-(1-Phenyl-2-carbalkoxy-vinyl)-thionophosphoric (phosphonic) acid esters and ester-amides and method for combatting insects |
Also Published As
Publication number | Publication date |
---|---|
BE563003A (de) | |
CH353007A (de) | 1961-03-31 |
FR1190017A (fr) | 1959-10-08 |
DE1197271B (de) | 1965-07-22 |
GB875583A (en) | 1961-08-23 |
NL222265A (de) |
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