US3247223A - Cyclic mercaptals - Google Patents
Cyclic mercaptals Download PDFInfo
- Publication number
- US3247223A US3247223A US202686A US20268662A US3247223A US 3247223 A US3247223 A US 3247223A US 202686 A US202686 A US 202686A US 20268662 A US20268662 A US 20268662A US 3247223 A US3247223 A US 3247223A
- Authority
- US
- United States
- Prior art keywords
- percent
- theory
- methyl
- grams
- yield
- 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 - Lifetime
Links
- 125000004122 cyclic group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000012360 testing method Methods 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- CARJCVDELAMAEJ-UHFFFAOYSA-N 2-methyl-1,3-dithiolane Chemical compound CC1SCCS1 CARJCVDELAMAEJ-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SFLGIMGLWCVAHP-UHFFFAOYSA-N 5h-oxathiole Chemical compound C1OSC=C1 SFLGIMGLWCVAHP-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 241000258913 Oncopeltus fasciatus Species 0.000 description 2
- 241000254112 Tribolium confusum Species 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000003129 miticidal effect Effects 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 1
- QNNPPEKCYFEVCF-UHFFFAOYSA-N 2-methyl-1,3-oxathiolane Chemical compound CC1OCCS1 QNNPPEKCYFEVCF-UHFFFAOYSA-N 0.000 description 1
- -1 4-oxo-phenyl Chemical group 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000207543 Euphorbia heterophylla Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000231739 Rutilus rutilus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ZGDKVKUWTCGYOA-URGPHPNLSA-N [4-[4-[(z)-c-(4-bromophenyl)-n-ethoxycarbonimidoyl]piperidin-1-yl]-4-methylpiperidin-1-yl]-(2,4-dimethyl-1-oxidopyridin-1-ium-3-yl)methanone Chemical compound C=1C=C(Br)C=CC=1C(=N/OCC)\C(CC1)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)C=C[N+]([O-])=C1C ZGDKVKUWTCGYOA-URGPHPNLSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 244000045947 parasite Species 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000843 powder 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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
- C07F9/547—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
- C07F9/65515—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 five-membered ring
-
- 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
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- 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
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655363—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a six-membered ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/08—Systemic pesticides
Definitions
- the new compounds of this invention may be represented by the following formula:
- R and R are lower alkyl radicals
- R is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 5 carbon atoms
- R? is selected from the group consisting of methylene and carbonyl
- n is an integer from 1 to 2
- the groups represented by X are independently selected from the group consisting of oxygen and sulfur, and X and X are independently selected from the group consisting of oxygen and sulfur, at least one of them being sulfur
- Y is selected from the group consisting of alkylene radicals having from 1 to 3 carbon atoms and phenylene
- Z is selected from the group consisting of hydrogen and carbethoxy.
- Suitable alkyl radicals for R and R include methyl, ethyl, propyl, isopropyl, :amyl, octyl, and the like.v
- Preparation of the compounds of the present invention is accomplished by reacting a phosphorylated aldehyde or ketone with a glycol or monoor dimercaptan, preferably in the presence of an acid catalyst. This reaction may be represented by the following equation:
- R, R R X, X X Y, Z, and n are as described hereinbefore.
- a solvent such as benzene and ethyl ether may be used but is not strictly essential to the process.
- suitable acid catalysts for the reaction are boron trifiuoride etherate and gaseous HCl.
- the reaction may be carried out at temperatures between 0 C. and 100 C. but preferably between about 20 C.
- Pesticidal activity for the compounds of the foregoing examples is illustrated in Table I wherein the percentage kill is reported for a specified quantity of the candidate pesticide expressed in micrograms (hereafter termed the bio-assay test), or for a percentage concentration in aque- XA 10 E MPLES CH ous dispersion (hereafter termed the screening test).
- a H a slanted line is used to separate the percentage kill, shown a )2 2 -C s on the left, and the percentage concentraion or quantity,
- Table I Compound House flies, American Milkweed Confused Two-spotted Two-spotted Two-spotted (example number) percent; roach, bug, percent flour beetle, mite post mite eggs, mite systemic,
- the following new compounds may also be prepared in reasonable yields when using the desired phosphorylated aldehyde or ketone with the corresponding glycol or mercaptan.
- This solution was diluted with water containing 0.015% Vatsol (a sulfonate-type wetting agent) and 0.005% Methocel (methyl cellulose) as emulsifiers, the amount of water being sufficient to dilute the active ingredients to a concentration of 0.1% or below.
- Vatsol a sulfonate-type wetting agent
- Methocel methyl cellulose
- the bean plants were infested with several hundred mites and then sprayed to run-off with an aqueous test dispersion prepared as described above. Sprayed plants were transferred to a greenhouse and held for 14 days.
- the miticidal and ovicidal activity of the test compounds were determined after 7 to 14 days. The 14 day reading was necessary for evaluating ovicidal action. Percentage mortality is reported, as shown in Table I, for both post embryonic and embryonic forms.
- pinto bean plants were placed in bottles containing 200 ml.
- the compounds may also be used in the form of emulsions, non-aqueous emulsions, wettable powders, vapors, and dusts, as may be best suited for the conditions of use.
- the toxic material may even be used in a pure undiluted form.
- pest is used herein in the restricted sense generally recognized in the art as applying to the lower forms of life customarily controlled .by chemical means and excluding the higher animals, the vertebrates, for example, rodents, birds, and larger forms which are more commonly controlled by mechanical means such as traps. In its broadest usage, the term refers to both the destructive and annoying household and plant organisms, especially .the parasites and pathogens. It will be apparent to one skilled in the art that the activity demonstrated on the selected insects and mites is indicative of activity in various species and orders not specifically shown.
- R and R are lower alkyl, R is selected from the group consisting of hydrogen and alkyl having from 1 to 5 carbon atoms, R is selected from the group consisting of methylene and carbonyl, n is an integer from 1 to 2; the groups represented by X are independently selected from the group consisting of oxygen and sulfur, and X and X are independently selected from the group consisting of oxygen and sulfur, at least one of them being sulfur; Y is selected from the group consisting of alkylene having from 1 to 3 carbon atoms and phenylene; and Z is selected from the group consisting of hydrogen and carbethoxy.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE633592D BE633592A (nl) | 1962-06-15 | ||
| NL294012D NL294012A (nl) | 1962-06-15 | ||
| US202686A US3247223A (en) | 1962-06-15 | 1962-06-15 | Cyclic mercaptals |
| GB21743/63A GB1025569A (en) | 1962-06-15 | 1963-05-30 | Phosphorus-containing cyclic acetals and mercaptals |
| FR937913A FR1375750A (fr) | 1962-06-15 | 1963-06-12 | Acétals et mercaptals cycliques |
| CH1710966A CH430320A (de) | 1962-06-15 | 1963-06-13 | Verwendung von cyclischen Mercaptalen und Acetalen zur Bekämpfung von tierischen Schädlingen |
| CH738263A CH428764A (de) | 1962-06-15 | 1963-06-13 | Verfahren zur Herstellung von cyclischen Mercaptalen und Acetalen und deren Verwendung |
| BR149862/63A BR6349862D0 (pt) | 1962-06-15 | 1963-06-14 | Processo de preparacao de novos compostos ciclicos fosforados e seu uso como praguicidas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202686A US3247223A (en) | 1962-06-15 | 1962-06-15 | Cyclic mercaptals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3247223A true US3247223A (en) | 1966-04-19 |
Family
ID=22750868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US202686A Expired - Lifetime US3247223A (en) | 1962-06-15 | 1962-06-15 | Cyclic mercaptals |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3247223A (nl) |
| BE (1) | BE633592A (nl) |
| BR (1) | BR6349862D0 (nl) |
| CH (2) | CH430320A (nl) |
| GB (1) | GB1025569A (nl) |
| NL (1) | NL294012A (nl) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3317561A (en) * | 1963-05-29 | 1967-05-02 | American Cyanamid Co | New heterocyclic organo-phosphate compounds |
| US3427147A (en) * | 1966-08-15 | 1969-02-11 | Olin Mathieson | Iminodioxolanes as herbicides |
| US4216222A (en) * | 1979-07-30 | 1980-08-05 | Stauffer Chemical Company | Alkyl or alkoxy-O-alkyl-S-[N-(2-alkyl, phenyl or vinyl-1,3-dioxolan-4-yl) methylaminoacetyl] dithiophosphates or phosphonates as insecticides and acaricides |
| US4230720A (en) * | 1979-07-30 | 1980-10-28 | Stauffer Chemical Company | Heterocyclic dithiophosphates or phosphonates as insecticides and acaricides |
| US4237056A (en) * | 1979-07-26 | 1980-12-02 | Velsicol Chemical Corporation | Cyclic acetal-methyl-carbamoyl-methyl esters of phosphonic and phosphoric acid |
| US4262012A (en) * | 1972-11-03 | 1981-04-14 | Ciba-Geigy Corporation | O-Methyl/ethyl-s-propyl/butyl-o-phenyl thiophosphates and dithiophosphates having an s-heterocyclic group on the phenyl ring |
| US4314840A (en) * | 1979-07-26 | 1982-02-09 | Velsicol Chemical Corporation | Cyclic acetal-methyl-carbamoyl-methyl esters of phosphonic and phosphoric acids, as herbicides |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE510817A (nl) * | 1951-04-20 | 1900-01-01 | ||
| US2701253A (en) * | 1955-02-01 | Substituted dithiolanes | ||
| US2789124A (en) * | 1951-07-02 | 1957-04-16 | Allied Chem & Dye Corp | Organic phosphate compounds and method of preparation and use thereof |
| US2815350A (en) * | 1955-08-30 | 1957-12-03 | Hercules Powder Co Ltd | Method of preparing organic dithiophosphoric acid compounds |
| US2853416A (en) * | 1955-09-19 | 1958-09-23 | Gen Aniline & Film Corp | Method of protecting plants by applying a pesticidal amount of a polyvinylpyrrolidone-iodine adduct |
| US2920997A (en) * | 1955-02-14 | 1960-01-12 | Pittsburgh Coke And Chemical C | Fungicidal composition of a hydantoin selected from the group consisting of 5, 5 polymethylene and 5, 5 diaryl, and 5, 5 aryl, alky hydantion |
| US3053852A (en) * | 1958-08-21 | 1962-09-11 | Eastman Kodak Co | Phosphorothiolothionates derived from vinylene carbonate and vinylene sulfite |
| US3071594A (en) * | 1960-07-23 | 1963-01-01 | Bayer Ag | Thiophosphoric acid esters and processes for their production |
-
0
- NL NL294012D patent/NL294012A/xx unknown
- BE BE633592D patent/BE633592A/xx unknown
-
1962
- 1962-06-15 US US202686A patent/US3247223A/en not_active Expired - Lifetime
-
1963
- 1963-05-30 GB GB21743/63A patent/GB1025569A/en not_active Expired
- 1963-06-13 CH CH1710966A patent/CH430320A/de unknown
- 1963-06-13 CH CH738263A patent/CH428764A/de unknown
- 1963-06-14 BR BR149862/63A patent/BR6349862D0/pt unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701253A (en) * | 1955-02-01 | Substituted dithiolanes | ||
| BE510817A (nl) * | 1951-04-20 | 1900-01-01 | ||
| US2789124A (en) * | 1951-07-02 | 1957-04-16 | Allied Chem & Dye Corp | Organic phosphate compounds and method of preparation and use thereof |
| US2920997A (en) * | 1955-02-14 | 1960-01-12 | Pittsburgh Coke And Chemical C | Fungicidal composition of a hydantoin selected from the group consisting of 5, 5 polymethylene and 5, 5 diaryl, and 5, 5 aryl, alky hydantion |
| US2815350A (en) * | 1955-08-30 | 1957-12-03 | Hercules Powder Co Ltd | Method of preparing organic dithiophosphoric acid compounds |
| US2853416A (en) * | 1955-09-19 | 1958-09-23 | Gen Aniline & Film Corp | Method of protecting plants by applying a pesticidal amount of a polyvinylpyrrolidone-iodine adduct |
| US3053852A (en) * | 1958-08-21 | 1962-09-11 | Eastman Kodak Co | Phosphorothiolothionates derived from vinylene carbonate and vinylene sulfite |
| US3071594A (en) * | 1960-07-23 | 1963-01-01 | Bayer Ag | Thiophosphoric acid esters and processes for their production |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3317561A (en) * | 1963-05-29 | 1967-05-02 | American Cyanamid Co | New heterocyclic organo-phosphate compounds |
| US3427147A (en) * | 1966-08-15 | 1969-02-11 | Olin Mathieson | Iminodioxolanes as herbicides |
| US4262012A (en) * | 1972-11-03 | 1981-04-14 | Ciba-Geigy Corporation | O-Methyl/ethyl-s-propyl/butyl-o-phenyl thiophosphates and dithiophosphates having an s-heterocyclic group on the phenyl ring |
| US4237056A (en) * | 1979-07-26 | 1980-12-02 | Velsicol Chemical Corporation | Cyclic acetal-methyl-carbamoyl-methyl esters of phosphonic and phosphoric acid |
| US4314840A (en) * | 1979-07-26 | 1982-02-09 | Velsicol Chemical Corporation | Cyclic acetal-methyl-carbamoyl-methyl esters of phosphonic and phosphoric acids, as herbicides |
| US4216222A (en) * | 1979-07-30 | 1980-08-05 | Stauffer Chemical Company | Alkyl or alkoxy-O-alkyl-S-[N-(2-alkyl, phenyl or vinyl-1,3-dioxolan-4-yl) methylaminoacetyl] dithiophosphates or phosphonates as insecticides and acaricides |
| US4230720A (en) * | 1979-07-30 | 1980-10-28 | Stauffer Chemical Company | Heterocyclic dithiophosphates or phosphonates as insecticides and acaricides |
Also Published As
| Publication number | Publication date |
|---|---|
| CH428764A (de) | 1967-01-31 |
| NL294012A (nl) | |
| CH430320A (de) | 1967-02-15 |
| BE633592A (nl) | |
| GB1025569A (en) | 1966-04-14 |
| BR6349862D0 (pt) | 1973-06-26 |
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