EP0000127B1 - Insektizide und akarizide Mischungen, deren Herstellung und Verwendung - Google Patents
Insektizide und akarizide Mischungen, deren Herstellung und Verwendung Download PDFInfo
- Publication number
- EP0000127B1 EP0000127B1 EP78100117A EP78100117A EP0000127B1 EP 0000127 B1 EP0000127 B1 EP 0000127B1 EP 78100117 A EP78100117 A EP 78100117A EP 78100117 A EP78100117 A EP 78100117A EP 0000127 B1 EP0000127 B1 EP 0000127B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- spp
- methyl
- ester
- phosphoric acid
- alkyl
- 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
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- VDTIMXCBOXBHER-UHFFFAOYSA-N hydroxy-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical class OP(S)(S)=S VDTIMXCBOXBHER-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- NTUYIOCWFBKOFV-UHFFFAOYSA-N methyl-(3,4,5-trimethylphenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC(C)=C(C)C(C)=C1 NTUYIOCWFBKOFV-UHFFFAOYSA-N 0.000 description 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
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- DJYCQTIURWJIOD-UHFFFAOYSA-N pentyl bis(prop-2-ynyl) phosphate Chemical compound CCCCCOP(=O)(OCC#C)OCC#C DJYCQTIURWJIOD-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
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- HHVMYKUJAKXQTA-UHFFFAOYSA-N propan-2-yl bis(prop-2-ynyl) phosphate Chemical compound C#CCOP(=O)(OC(C)C)OCC#C HHVMYKUJAKXQTA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- AIKFSRURHOARNU-UHFFFAOYSA-N propyl bis(prop-2-ynyl) phosphate Chemical compound CCCOP(=O)(OCC#C)OCC#C AIKFSRURHOARNU-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FCTINJHSYHFASK-UHFFFAOYSA-N tris(prop-2-ynyl) phosphate Chemical compound C#CCOP(=O)(OCC#C)OCC#C FCTINJHSYHFASK-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
- C07F9/28—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
-
- 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
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur 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 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
- C07F9/28—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
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3217—Esters of acyclic unsaturated 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
- C07F9/28—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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
Definitions
- the present invention relates to new insecticidal and acaricidal synergistic active substance combinations of partially known phosphorus-containing compounds and pesticidal active substances.
- synergistic mixtures of carbamates e.g. B. 2-iso-propoxyphenyl-N-methyl carbamate or phosphoric acid esters, e.g. O, O-diethyl-O- (2-isopropyl-4-methyl-pyrimidinyl- [6] -phosphorothioate, or of natural or synthetic pyrethroids with piperonyl ethers, such as, for example, ⁇ - [2- (2-butoxyethoxy) - ethoxy] -4,5-methylenedioxy-2-propyl-toluene, known (cf. Bull, Org. -Health Org.
- the insecticidal and / or acaricidal action of the active compound combinations according to the invention is significantly higher than the action of the individual component or the sum of the actions of the individual components. It is also significantly higher than the effect of the already known combinations of active substances consisting of 2-iso-propoxy-phenyl-N-methyl-carbamate and piperonyl butoxide.
- synergistic mixtures which contain the unsaturated organic phosphates of the formula I which can be used according to the invention are a valuable addition to the technology.
- the unsaturated organic phosphates of the formula are known and can be obtained by customary processes.
- the unsaturated organic phosphates of the general formula I which can be used according to the invention include phosphoric acid esters, thiophosphoric acid esters, dithio and trithiophosphoric acid esters.
- the production of (thio) phosphoric acid esters is described in detail, for example, in “Houben-Weyl, Methods of Organic Chemistry, Vol. 12/1 and Vol. 12/2”.
- radicals R 1 , R 2 and R 3 must stand for a radical which is unsaturated in the 2-position, the allyl radical being particularly preferred.
- the new active ingredient combinations of the unsaturated organic phosphates which can be used according to the invention with carbamates show an outstanding increase in activity compared to the individual active ingredients or their sum.
- the weight ratios of the active ingredient groups can fluctuate in relatively large ranges.
- the phosphorus-containing compounds used as synergists with the other active ingredients are used in a ratio of 0.1: 10 to 10: 0.1.
- Mixing ratios of 0.5: 1.0 to 3.0: 1.0 have proven to be particularly suitable.
- the active substance combinations according to the invention not only bring about a quick knock-down effect, but also bring about the sustainable killing of animal pests, in particular insects and mites, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species and against all or individual stages of development.
- the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates.
- formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
- extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
- surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
- organic solvents can also be used as auxiliary solvents.
- aromatics such as xylene, toluene, or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
- Petroleum fractions oil fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g.
- Aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules: broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-generating agents: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
- alkylaryl polyglycol ether alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as a dispersant: e.g. Lignin, sulfite liquor and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, can be used in the formulations; Polyvinyl alcohol, polyvinyl acetate.
- Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo-metal phthatoeyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
- the active compound combinations according to the invention are used in the form of their commercially available formulation and / or the use forms prepared from these formulations.
- the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
- the active substance concentration of the use form can be from 0.0000001 to 100% by weight of active substance, preferably between 0.01 and 10% by weight.
- the application takes place in a customary manner adapted to the application forms.
- the active substance combinations are notable for an excellent residual action on wood and clay and for good stability to alkali on limed substrates. example
- Test animals Phosphoric acid ester-resistant Musca domestica (Weymann strain)
- Solutions are prepared from the active ingredients, synergists and mixtures of active ingredients and synergists and 2.5 ml of this is pipetted into Petri dishes on filter paper disks with a diameter of 9.5 cm. The filter paper absorbs the solutions. The petri dishes remain open until the solvent has completely evaporated. Then put 25 test animals in the Petri dishes and cover them with a glass lid.
- the condition of the test animals is checked continuously for up to 6 hours. The time required for a 100% knock-down effect is determined. If the LT 100 is not reached after 6 hours, the percentage of the knock-down test animals is determined.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE7979105303T DE2862180D1 (en) | 1977-06-18 | 1978-06-08 | Phosphoric acid esters and their use in pesticidal compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2727479 | 1977-06-08 | ||
| DE19772727479 DE2727479A1 (de) | 1977-06-18 | 1977-06-18 | Insektizide und akarizide mittel |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79105303.6 Division-Into | 1979-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000127A1 EP0000127A1 (de) | 1979-01-10 |
| EP0000127B1 true EP0000127B1 (de) | 1982-10-20 |
Family
ID=6011788
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79105303A Expired EP0012452B1 (de) | 1977-06-18 | 1978-06-08 | Phosphorsäureester und deren Verwendung zur Herstellung von Schädlingsbekämpfungsmitteln |
| EP78100117A Expired EP0000127B1 (de) | 1977-06-18 | 1978-06-08 | Insektizide und akarizide Mischungen, deren Herstellung und Verwendung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79105303A Expired EP0012452B1 (de) | 1977-06-18 | 1978-06-08 | Phosphorsäureester und deren Verwendung zur Herstellung von Schädlingsbekämpfungsmitteln |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4257987A (xx) |
| EP (2) | EP0012452B1 (xx) |
| JP (1) | JPS548724A (xx) |
| AT (1) | AT358331B (xx) |
| AU (1) | AU522512B2 (xx) |
| BR (1) | BR7803843A (xx) |
| CA (1) | CA1107641A (xx) |
| DE (3) | DE2727479A1 (xx) |
| DK (1) | DK271278A (xx) |
| EG (1) | EG13871A (xx) |
| IL (1) | IL54923A (xx) |
| IT (1) | IT7824658A0 (xx) |
| NZ (1) | NZ187577A (xx) |
| PH (1) | PH15766A (xx) |
| PT (1) | PT68165A (xx) |
| TR (1) | TR20354A (xx) |
| ZA (1) | ZA783474B (xx) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2926652A1 (de) * | 1979-07-02 | 1981-01-22 | Bayer Ag | Verfahren zur herstellung von phosphorsaeurepropargylestern |
| DE2936037A1 (de) * | 1979-09-06 | 1981-04-09 | Bayer Ag, 5090 Leverkusen | Propargylgruppenhaltige methanphosphonsaeureester und deren verwendung in synergistischen wirkstoffkombinationen zur schaedlingsbekaempfung |
| DE2949391A1 (de) * | 1979-12-07 | 1981-07-16 | Bayer Ag, 5090 Leverkusen | Insektizide und akarizide mittel entaltend propargylthionophophorsaeureester |
| 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 |
| EP0053100B1 (de) * | 1980-11-25 | 1984-09-19 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| US4472390A (en) * | 1980-12-31 | 1984-09-18 | Rhone-Poulenc Agrochimie | S-Alkyls-(tertiary alkyl) alkylphosphonodithioate insecticides and nematocides |
| JPS57134493A (en) * | 1981-02-12 | 1982-08-19 | Sankin Kogyo Kk | Phosphoric ester derivative |
| US4419350A (en) * | 1981-11-05 | 1983-12-06 | Stauffer Chemical Company | Carbofuran compositions for problem soils |
| US4933181A (en) * | 1983-11-28 | 1990-06-12 | Clemson University | Synergistic insecticidal compositions and method for use of same |
| JPS60224606A (ja) * | 1984-04-23 | 1985-11-09 | Kao Corp | 農薬組成物 |
| DE3431256A1 (de) * | 1984-08-24 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Phosphorheterocyclen enthaltende schaedlingsbekaempfungsmittel |
| EP0181131A3 (en) * | 1984-11-01 | 1987-05-20 | Kent Scientific and Industrial Projects Limited | Apparatus for detecting the resonant frequency of a bone |
| US5057235A (en) * | 1988-06-23 | 1991-10-15 | Mobil Oil Corporation | Sulfur-phosphorus adducts of chromium catalyzed polyalphaolefins |
| GB0211924D0 (en) * | 2002-05-23 | 2002-07-03 | Syngenta Ltd | Composition |
| CN109942622B (zh) * | 2017-12-20 | 2021-10-15 | 张家港市国泰华荣化工新材料有限公司 | 一种含不饱和烃的磷酸酯阻燃剂的制备方法 |
| JP2023542806A (ja) * | 2020-08-10 | 2023-10-12 | ノームズ テクノロジーズ インコーポレイテッド | リチウムイオン電池用の不飽和添加剤 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2693483A (en) * | 1952-03-06 | 1954-11-02 | Dow Chemical Co | Propynyl phosphate compounds |
| NL103634C (xx) * | 1957-09-24 | |||
| US2906661A (en) * | 1958-03-18 | 1959-09-29 | Monsanto Chemicals | Treating agricultural soils with propargyl phosphorothioates |
| US3513233A (en) * | 1967-02-15 | 1970-05-19 | Chemagro Corp | Use of allylphosphonodithioates as nematocides |
| US4028438A (en) * | 1967-05-17 | 1977-06-07 | Sumitomo Chemical Company, Limited | Phosphorothiolates |
| UST869008I4 (en) * | 1969-03-27 | 1969-12-16 | Defensive publication | |
| US3860711A (en) * | 1970-04-30 | 1975-01-14 | Johnson & Son Inc S C | Synergistic insecticidal composition containing dipropargyl phenylphosphonate |
| US3917476A (en) * | 1970-10-28 | 1975-11-04 | Gates Rubber Co | Diethyl alpha phosphonate as an (antimicrobial agent) algaecide |
| US3885031A (en) * | 1971-03-08 | 1975-05-20 | Fmc Corp | Insecticidal compositions and methods of combatting insects using cyclopropane carboxylate insecticides with a synergistic compound of mono (alkyl and alkenyl) mono omega-alkynyl arylphosphonates |
| US3862999A (en) * | 1971-03-11 | 1975-01-28 | Stauffer Chemical Co | O{3 beta alkane phosphates |
| US3783016A (en) * | 1971-06-01 | 1974-01-01 | D Randall | Method for imparting flame resistance to fibrous materials |
| DE2131402A1 (de) * | 1971-06-24 | 1972-12-28 | Basf Ag | Dithiophosphorsaeureester |
| US3780144A (en) * | 1971-09-10 | 1973-12-18 | Alelio G D | Halogenated ethylenically unsaturated phosphates |
| JPS5139212B2 (xx) * | 1971-09-25 | 1976-10-26 | ||
| BE793572A (fr) * | 1971-12-30 | 1973-06-29 | Sumitomo Chemical Co | Nouveaux derives thiophosphores a activite |
| US3819756A (en) * | 1972-05-24 | 1974-06-25 | Basf Ag | Dithiophosphoric esters |
| JPS4928972A (xx) * | 1972-07-13 | 1974-03-14 | ||
| US3856896A (en) * | 1973-02-09 | 1974-12-24 | Johnson & Son Inc S C | Alkyl propargyl phosphonates |
| JPS5325303B2 (xx) * | 1973-05-24 | 1978-07-26 | ||
| JPS5016344A (xx) * | 1973-06-15 | 1975-02-20 | ||
| JPS5016853A (xx) * | 1973-06-21 | 1975-02-21 | ||
| JPS5754484B2 (xx) * | 1973-10-30 | 1982-11-18 | ||
| JPS51118834A (en) * | 1975-03-28 | 1976-10-19 | Mitsubishi Chem Ind Ltd | An insecticide composition against resistant noxious insects |
| IL48428A0 (en) * | 1974-11-15 | 1976-03-31 | Fmc Corp | Synergistic insecticidal compositions containing a cyclopropane carboxylate and a phosphonate |
-
1977
- 1977-06-18 DE DE19772727479 patent/DE2727479A1/de not_active Withdrawn
-
1978
- 1978-06-08 PH PH21242A patent/PH15766A/en unknown
- 1978-06-08 DE DE7878100117T patent/DE2862060D1/de not_active Expired
- 1978-06-08 EP EP79105303A patent/EP0012452B1/de not_active Expired
- 1978-06-08 EP EP78100117A patent/EP0000127B1/de not_active Expired
- 1978-06-08 DE DE7979105303T patent/DE2862180D1/de not_active Expired
- 1978-06-12 PT PT68165A patent/PT68165A/pt unknown
- 1978-06-14 AU AU37103/78A patent/AU522512B2/en not_active Expired
- 1978-06-15 TR TR20354A patent/TR20354A/xx unknown
- 1978-06-15 IL IL54923A patent/IL54923A/xx unknown
- 1978-06-15 NZ NZ187577A patent/NZ187577A/xx unknown
- 1978-06-16 AT AT440378A patent/AT358331B/de not_active IP Right Cessation
- 1978-06-16 DK DK271278A patent/DK271278A/da unknown
- 1978-06-16 ZA ZA00783474A patent/ZA783474B/xx unknown
- 1978-06-16 BR BR787803843A patent/BR7803843A/pt unknown
- 1978-06-16 CA CA305,680A patent/CA1107641A/en not_active Expired
- 1978-06-16 IT IT7824658A patent/IT7824658A0/it unknown
- 1978-06-16 JP JP7227378A patent/JPS548724A/ja active Pending
- 1978-06-17 EG EG373/78A patent/EG13871A/xx active
-
1979
- 1979-09-17 US US06/076,053 patent/US4257987A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0012452A3 (en) | 1980-07-23 |
| IL54923A (en) | 1982-12-31 |
| AU3710378A (en) | 1979-12-20 |
| BR7803843A (pt) | 1979-02-20 |
| PH15766A (en) | 1983-03-24 |
| IL54923A0 (en) | 1978-08-31 |
| EP0012452B1 (de) | 1983-02-09 |
| DE2862060D1 (en) | 1982-11-25 |
| TR20354A (tr) | 1981-02-23 |
| ZA783474B (en) | 1979-06-27 |
| PT68165A (en) | 1978-07-01 |
| EP0000127A1 (de) | 1979-01-10 |
| EG13871A (en) | 1982-09-30 |
| NZ187577A (en) | 1980-05-27 |
| DE2727479A1 (de) | 1979-01-04 |
| AU522512B2 (en) | 1982-06-10 |
| EP0012452A2 (de) | 1980-06-25 |
| DE2862180D1 (en) | 1983-03-17 |
| ATA440378A (de) | 1980-01-15 |
| AT358331B (de) | 1980-09-10 |
| US4257987A (en) | 1981-03-24 |
| DK271278A (da) | 1978-12-19 |
| CA1107641A (en) | 1981-08-25 |
| JPS548724A (en) | 1979-01-23 |
| IT7824658A0 (it) | 1978-06-16 |
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