EP0000127A1 - Compositions insecticides et acaricides, leur préparation et leur application - Google Patents
Compositions insecticides et acaricides, leur préparation et leur application Download PDFInfo
- Publication number
- EP0000127A1 EP0000127A1 EP78100117A EP78100117A EP0000127A1 EP 0000127 A1 EP0000127 A1 EP 0000127A1 EP 78100117 A EP78100117 A EP 78100117A EP 78100117 A EP78100117 A EP 78100117A EP 0000127 A1 EP0000127 A1 EP 0000127A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ester
- acid
- spp
- allyl
- methyl
- 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.)
- Granted
Links
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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
-
- 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 System
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids R2P(=O)(OH); Thiophosphinic acids, i.e. R2P(=X)(XH) (X = S, 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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—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. B. 0.0-diethyl-0- (2-isopropyl-4-methyl-pyrimidinyl- [6]) - phosphorothioate, or of natural or synthetic pyrethroids with piperonyl ethers, such as. B. ⁇ - [2- (2-butoxy-ethoxy) -ethoxy] -4,5-methylenedioxy-2-propyl-toluene, known (see Bull, Org.-Health Org.
- the insecticidal and / or acaricidal action of the active compound combinations according to the invention is substantially 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.
- the phosphorus-containing compounds which can be used according to the invention as synergists show excellent synergistic activity not only with one class of active compound, but with active compounds from a wide variety of chemical groups.
- synergistic mixtures which contain the phosphorus-containing compounds of the formula I which can be used according to the invention are a valuable addition to the technology.
- radicals R 1 , R 2 and R 3 must stand for a radical which is unsaturated in the 2-position; the allyl radical is particularly preferred.
- the new active compound combinations of the phosphorus esters of the formula (I) which can be used according to the invention show with carbamates, encycloalkanen Carbonklareestern, Phosphorklareestern, halo and g haloalkanes excellent WIR kun g ss annoying compared to the single active ingredients or with respect to their sum.
- the weight ratios of W vary within relatively wide ranges.
- the phosphorus-containing compounds used as synergists are used in a ratio of 0.1: 10 to 10: 0.1 with the other active ingredients. Mixing ratios of 0.5: 1.0 to 3.0: 1.0 have proven to be particularly suitable.
- the active compound 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 products and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as 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 prepared in a known manner, e.g. B. 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.
- 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. B.
- Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers; natural rock flours, such as kaolins, alumina, talc ..
- alkylaryl -polyglykol ether alkyl sulfonates, A lkylsulfate, arylsulphonates and protein hydrolysates; as a dispersant: e.g. B. lignin, sulfite and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
- Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin. Azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- inorganic pigments e.g. B. iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin.
- Azo metal phthalocyanine 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 up to 100 wt .-% active ingredient, preferably between 0.01 and 10 wt .-%.
- the application takes place in a customary manner adapted to the application forms.
- the active substance combinations When used against hygiene pests and pests of stored products, the active substance combinations are notable for an excellent residual action on wood and clay and for good stability to alkali on limed substrates.
- 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 these are pipetted into Petri dishes on filter paper discs 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 25 test animals are placed in the Petri dishes and covered 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.
- Test animals Blattella germanica Tribolium confusum Trogoderma granarium 4. Larvae
- Solutions are prepared from the active ingredients, synergists and mixtures of active ingredients and synergists and 2.5 ml of these are pipetted into petri dishes on filter paper of 9.5 cm diameter.
- the filter paper absorbs the solutions.
- the petri dishes remain open until the solvent has completely evaporated. Then put 20 test animals in the Petri dishes and cover them with a glass lid.
- the condition of the animals is checked continuously for up to 6 hours and then after 24, 48 and 72 hours. The time required for a 100% knock-down effect is determined. If the LT 100 is not reached after 72 hours, the percentage of the knock-down test animals is determined.
Landscapes
- 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 | 1977-06-18 | ||
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 true EP0000127A1 (fr) | 1979-01-10 |
EP0000127B1 EP0000127B1 (fr) | 1982-10-20 |
Family
ID=6011788
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79105303A Expired EP0012452B1 (fr) | 1977-06-18 | 1978-06-08 | Esters d'acides phosphoriques et leur utilisation dans des compositions pesticides |
EP78100117A Expired EP0000127B1 (fr) | 1977-06-18 | 1978-06-08 | Compositions insecticides et acaricides, leur préparation et leur application |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79105303A Expired EP0012452B1 (fr) | 1977-06-18 | 1978-06-08 | Esters d'acides phosphoriques et leur utilisation dans des compositions pesticides |
Country Status (17)
Country | Link |
---|---|
US (1) | US4257987A (fr) |
EP (2) | EP0012452B1 (fr) |
JP (1) | JPS548724A (fr) |
AT (1) | AT358331B (fr) |
AU (1) | AU522512B2 (fr) |
BR (1) | BR7803843A (fr) |
CA (1) | CA1107641A (fr) |
DE (3) | DE2727479A1 (fr) |
DK (1) | DK271278A (fr) |
EG (1) | EG13871A (fr) |
IL (1) | IL54923A (fr) |
IT (1) | IT7824658A0 (fr) |
NZ (1) | NZ187577A (fr) |
PH (1) | PH15766A (fr) |
PT (1) | PT68165A (fr) |
TR (1) | TR20354A (fr) |
ZA (1) | ZA783474B (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0021361A1 (fr) * | 1979-07-02 | 1981-01-07 | Bayer Ag | Procédé de préparation d'esters propargyliques d'acide phosphorique |
EP0030661A2 (fr) * | 1979-12-07 | 1981-06-24 | Bayer Ag | Agents insecticides et acaricides contenant des esters de propargyle d'acide thionophosphorique |
US4442239A (en) * | 1981-02-12 | 1984-04-10 | Sankin Industry Co., Ltd. | Phosphate derivatives, process for producing phosphate derivatives and fillers for human hard tissues containing the same |
EP0181131A2 (fr) * | 1984-11-01 | 1986-05-14 | Kent Scientific and Industrial Projects Limited | Dispositif pour la détermination de la fréquence de résonance d'un os |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2936037A1 (de) * | 1979-09-06 | 1981-04-09 | Bayer Ag, 5090 Leverkusen | Propargylgruppenhaltige methanphosphonsaeureester und deren verwendung in synergistischen wirkstoffkombinationen zur schaedlingsbekaempfung |
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 |
DE3166207D1 (en) * | 1980-11-25 | 1984-10-25 | Ciba Geigy Ag | Pesticide agents |
US4472390A (en) * | 1980-12-31 | 1984-09-18 | Rhone-Poulenc Agrochimie | S-Alkyls-(tertiary alkyl) alkylphosphonodithioate insecticides and nematocides |
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 |
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 |
EP4192891A1 (fr) * | 2020-08-10 | 2023-06-14 | Nohms Technologies, Inc. | Additif insaturé pour batterie au lithium-ion |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UST869008I4 (en) * | 1969-03-27 | 1969-12-16 | Defensive publication | |
US3513233A (en) * | 1967-02-15 | 1970-05-19 | Chemagro Corp | Use of allylphosphonodithioates as nematocides |
FR2166172A1 (fr) * | 1971-12-30 | 1973-08-10 | Sumitomo Chemical Co | |
FR2217346A1 (fr) * | 1973-02-09 | 1974-09-06 | Johnson & Son Inc S C | |
US3860711A (en) * | 1970-04-30 | 1975-01-14 | Johnson & Son Inc S C | Synergistic insecticidal composition containing dipropargyl phenylphosphonate |
US3862999A (en) * | 1971-03-11 | 1975-01-28 | Stauffer Chemical Co | O{3 beta alkane phosphates |
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 |
US3917476A (en) * | 1970-10-28 | 1975-11-04 | Gates Rubber Co | Diethyl alpha phosphonate as an (antimicrobial agent) algaecide |
US4028438A (en) * | 1967-05-17 | 1977-06-07 | Sumitomo Chemical Company, Limited | Phosphorothiolates |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2693483A (en) * | 1952-03-06 | 1954-11-02 | Dow Chemical Co | Propynyl phosphate compounds |
BE571029A (fr) * | 1957-09-24 | |||
US2906661A (en) * | 1958-03-18 | 1959-09-29 | Monsanto Chemicals | Treating agricultural soils with propargyl phosphorothioates |
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 (fr) * | 1971-09-25 | 1976-10-26 | ||
US3819756A (en) * | 1972-05-24 | 1974-06-25 | Basf Ag | Dithiophosphoric esters |
JPS4928972A (fr) * | 1972-07-13 | 1974-03-14 | ||
JPS5325303B2 (fr) * | 1973-05-24 | 1978-07-26 | ||
JPS5016344A (fr) * | 1973-06-15 | 1975-02-20 | ||
JPS5016853A (fr) * | 1973-06-21 | 1975-02-21 | ||
JPS5754484B2 (fr) * | 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 DE DE7878100117T patent/DE2862060D1/de not_active Expired
- 1978-06-08 EP EP79105303A patent/EP0012452B1/fr not_active Expired
- 1978-06-08 DE DE7979105303T patent/DE2862180D1/de not_active Expired
- 1978-06-08 PH PH21242A patent/PH15766A/en unknown
- 1978-06-08 EP EP78100117A patent/EP0000127B1/fr 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 NZ NZ187577A patent/NZ187577A/xx unknown
- 1978-06-15 TR TR20354A patent/TR20354A/xx unknown
- 1978-06-15 IL IL54923A patent/IL54923A/xx unknown
- 1978-06-16 AT AT440378A patent/AT358331B/de not_active IP Right Cessation
- 1978-06-16 ZA ZA00783474A patent/ZA783474B/xx unknown
- 1978-06-16 IT IT7824658A patent/IT7824658A0/it unknown
- 1978-06-16 DK DK271278A patent/DK271278A/da unknown
- 1978-06-16 JP JP7227378A patent/JPS548724A/ja active Pending
- 1978-06-16 BR BR787803843A patent/BR7803843A/pt unknown
- 1978-06-16 CA CA305,680A patent/CA1107641A/fr not_active Expired
- 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
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
FR2166172A1 (fr) * | 1971-12-30 | 1973-08-10 | Sumitomo Chemical Co | |
FR2217346A1 (fr) * | 1973-02-09 | 1974-09-06 | Johnson & Son Inc S C |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0021361A1 (fr) * | 1979-07-02 | 1981-01-07 | Bayer Ag | Procédé de préparation d'esters propargyliques d'acide phosphorique |
EP0030661A2 (fr) * | 1979-12-07 | 1981-06-24 | Bayer Ag | Agents insecticides et acaricides contenant des esters de propargyle d'acide thionophosphorique |
EP0030661A3 (fr) * | 1979-12-07 | 1981-07-08 | Bayer Ag | Agents insecticides et acaricides contenant des esters de propargyle d'acide thionophosphorique |
US4442239A (en) * | 1981-02-12 | 1984-04-10 | Sankin Industry Co., Ltd. | Phosphate derivatives, process for producing phosphate derivatives and fillers for human hard tissues containing the same |
EP0181131A2 (fr) * | 1984-11-01 | 1986-05-14 | Kent Scientific and Industrial Projects Limited | Dispositif pour la détermination de la fréquence de résonance d'un os |
EP0181131A3 (fr) * | 1984-11-01 | 1987-05-20 | Kent Scientific and Industrial Projects Limited | Dispositif pour la détermination de la fréquence de résonance d'un os |
Also Published As
Publication number | Publication date |
---|---|
PT68165A (en) | 1978-07-01 |
IL54923A0 (en) | 1978-08-31 |
AU3710378A (en) | 1979-12-20 |
ZA783474B (en) | 1979-06-27 |
DE2727479A1 (de) | 1979-01-04 |
AU522512B2 (en) | 1982-06-10 |
DK271278A (da) | 1978-12-19 |
ATA440378A (de) | 1980-01-15 |
NZ187577A (en) | 1980-05-27 |
EP0000127B1 (fr) | 1982-10-20 |
IT7824658A0 (it) | 1978-06-16 |
TR20354A (tr) | 1981-02-23 |
US4257987A (en) | 1981-03-24 |
PH15766A (en) | 1983-03-24 |
DE2862180D1 (en) | 1983-03-17 |
CA1107641A (fr) | 1981-08-25 |
DE2862060D1 (en) | 1982-11-25 |
EP0012452B1 (fr) | 1983-02-09 |
JPS548724A (en) | 1979-01-23 |
BR7803843A (pt) | 1979-02-20 |
EG13871A (en) | 1982-09-30 |
EP0012452A2 (fr) | 1980-06-25 |
AT358331B (de) | 1980-09-10 |
EP0012452A3 (en) | 1980-07-23 |
IL54923A (en) | 1982-12-31 |
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