DK142876B - Phosphorholdige benzoxazolderivater til anvendelse i insecticider og acaricider. - Google Patents
Phosphorholdige benzoxazolderivater til anvendelse i insecticider og acaricider. Download PDFInfo
- Publication number
- DK142876B DK142876B DK102976AA DK102976A DK142876B DK 142876 B DK142876 B DK 142876B DK 102976A A DK102976A A DK 102976AA DK 102976 A DK102976 A DK 102976A DK 142876 B DK142876 B DK 142876B
- Authority
- DK
- Denmark
- Prior art keywords
- compounds
- phosphorus
- solution
- acaricides
- insecticides
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 6
- 229910052698 phosphorus Inorganic materials 0.000 title description 6
- 239000011574 phosphorus Substances 0.000 title description 6
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title description 4
- 239000000642 acaricide Substances 0.000 title description 3
- 239000002917 insecticide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 description 25
- 239000000243 solution Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 10
- 230000000749 insecticidal effect Effects 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 8
- 241001454293 Tetranychus urticae Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000254086 Tribolium <beetle> Species 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000037406 food intake Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 230000001776 parthenogenetic effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- JINDZTHXQMYDAG-UHFFFAOYSA-N 1-(1,3-benzoxazol-2-yl)ethyl methanesulfonate Chemical compound C1=CC=C2OC(C(OS(C)(=O)=O)C)=NC2=C1 JINDZTHXQMYDAG-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- -1 methanol or ethanol Chemical compound 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- VWZPVYDIHHKSEE-UHFFFAOYSA-N 1-(1,3-benzoxazol-2-yl)ethanol Chemical compound C1=CC=C2OC(C(O)C)=NC2=C1 VWZPVYDIHHKSEE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241000510032 Ellipsaria lineolata Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000500439 Plutella 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000003226 decolorizating effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65324—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7507556 | 1975-03-11 | ||
FR7507556A FR2305415A1 (fr) | 1975-03-11 | 1975-03-11 | Nouveaux derives phosphores du benzoxazole et du benzothiazole, leur preparation et les compositions insecticides et acaricides qui les contiennent |
Publications (3)
Publication Number | Publication Date |
---|---|
DK102976A DK102976A (ja) | 1976-09-12 |
DK142876B true DK142876B (da) | 1981-02-16 |
DK142876C DK142876C (ja) | 1981-09-21 |
Family
ID=9152404
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK102976AA DK142876B (da) | 1975-03-11 | 1976-03-10 | Phosphorholdige benzoxazolderivater til anvendelse i insecticider og acaricider. |
Country Status (21)
Country | Link |
---|---|
US (1) | US4062951A (ja) |
JP (1) | JPS598280B2 (ja) |
AR (1) | AR221814A1 (ja) |
AU (1) | AU503181B2 (ja) |
BE (1) | BE839401A (ja) |
BR (1) | BR7601479A (ja) |
CA (1) | CA1064938A (ja) |
CH (1) | CH610906A5 (ja) |
DD (1) | DD125614A5 (ja) |
DE (1) | DE2608506C2 (ja) |
DK (1) | DK142876B (ja) |
ES (1) | ES445960A1 (ja) |
FR (1) | FR2305415A1 (ja) |
GB (1) | GB1492241A (ja) |
IL (1) | IL49193A (ja) |
IT (1) | IT1061626B (ja) |
NL (1) | NL7602506A (ja) |
OA (1) | OA05269A (ja) |
PT (1) | PT64891B (ja) |
SU (2) | SU651705A3 (ja) |
ZA (1) | ZA761481B (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4137308A (en) * | 1977-11-11 | 1979-01-30 | Stauffer Chemical Company | 1,3-Oxazole phosphates and phosphonates as insecticides and miticides |
US4618603A (en) * | 1982-03-31 | 1986-10-21 | Union Carbide Corporation | Alpha-heterocyclic carbinol phosphates |
US4425338A (en) | 1982-03-31 | 1984-01-10 | Union Carbide Corporation | Alpha-heterocyclic carbinol phosphates |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL99129C (ja) * | 1956-12-03 | |||
FR2755M (fr) * | 1962-07-27 | 1964-08-31 | Shionogi & Co | Nouveaux agents thérapeutiques possédant l'activité de la vitamine b1. |
US3580922A (en) * | 1964-12-28 | 1971-05-25 | Stauffer Chemical Co | Phosphorylated heterocyclic compounds |
NL131363C (ja) * | 1965-06-09 | Hoechst Ag | ||
AT259576B (de) * | 1965-06-09 | 1968-01-25 | Hoechst Ag | Verfahren zur Herstellung von neuen Mono- und Dithiophosphorsäureestern |
CH536071A (de) * | 1970-06-26 | 1973-04-30 | Agripat Sa | Insektizides und akarizides Mittel |
-
1975
- 1975-03-11 FR FR7507556A patent/FR2305415A1/fr active Granted
-
1976
- 1976-03-02 DE DE2608506A patent/DE2608506C2/de not_active Expired
- 1976-03-09 IT IT48490/76A patent/IT1061626B/it active
- 1976-03-10 DK DK102976AA patent/DK142876B/da unknown
- 1976-03-10 CH CH299076A patent/CH610906A5/xx not_active IP Right Cessation
- 1976-03-10 BE BE165023A patent/BE839401A/xx not_active IP Right Cessation
- 1976-03-10 DD DD191777A patent/DD125614A5/xx unknown
- 1976-03-10 PT PT64891A patent/PT64891B/pt unknown
- 1976-03-10 AR AR262498A patent/AR221814A1/es active
- 1976-03-10 ZA ZA761481A patent/ZA761481B/xx unknown
- 1976-03-10 IL IL49193A patent/IL49193A/xx unknown
- 1976-03-10 CA CA247,548A patent/CA1064938A/en not_active Expired
- 1976-03-10 NL NL7602506A patent/NL7602506A/xx not_active Application Discontinuation
- 1976-03-10 JP JP51026583A patent/JPS598280B2/ja not_active Expired
- 1976-03-11 ES ES445960A patent/ES445960A1/es not_active Expired
- 1976-03-11 BR BR7601479A patent/BR7601479A/pt unknown
- 1976-03-11 AU AU11887/76A patent/AU503181B2/en not_active Expired
- 1976-03-11 GB GB9817/76A patent/GB1492241A/en not_active Expired
- 1976-03-11 OA OA55763A patent/OA05269A/xx unknown
- 1976-03-11 US US05/665,871 patent/US4062951A/en not_active Expired - Lifetime
- 1976-03-11 SU SU762330501A patent/SU651705A3/ru active
- 1976-07-12 SU SU762378200A patent/SU645522A3/ru active
Also Published As
Publication number | Publication date |
---|---|
PT64891A (fr) | 1976-04-01 |
IL49193A0 (en) | 1976-05-31 |
ES445960A1 (es) | 1977-05-16 |
NL7602506A (nl) | 1976-09-14 |
DK102976A (ja) | 1976-09-12 |
BR7601479A (pt) | 1976-09-14 |
JPS51115468A (en) | 1976-10-12 |
GB1492241A (en) | 1977-11-16 |
AU503181B2 (en) | 1979-08-23 |
DE2608506C2 (de) | 1983-12-15 |
SU651705A3 (ru) | 1979-03-05 |
FR2305415B1 (ja) | 1977-11-25 |
IL49193A (en) | 1978-07-31 |
AU1188776A (en) | 1977-09-15 |
BE839401A (fr) | 1976-09-10 |
FR2305415A1 (fr) | 1976-10-22 |
DE2608506A1 (de) | 1976-09-30 |
IT1061626B (it) | 1983-04-30 |
OA05269A (fr) | 1981-02-28 |
JPS598280B2 (ja) | 1984-02-23 |
AR221814A1 (es) | 1981-03-31 |
DD125614A5 (ja) | 1977-05-04 |
US4062951A (en) | 1977-12-13 |
ZA761481B (en) | 1977-03-30 |
CH610906A5 (ja) | 1979-05-15 |
PT64891B (fr) | 1977-08-18 |
CA1064938A (en) | 1979-10-23 |
SU645522A3 (ru) | 1979-01-30 |
DK142876C (ja) | 1981-09-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4150142A (en) | Derivatives of alkoxy-5-phenyl-3 oxadiazoline-1,3,4 one-2, their preparation and insecticidal and acaricidal compositions which contain them | |
DK170333B1 (da) | Symmetriske N-substituerede bis-carbamoylsulfidforbindelser til anvendelse som insekticider og/eller miticider, insekticidt og/eller miticidt middel indeholdende mindst en af disse forbindelser samt fremgangsmåde til bekæmpelse af insekter og mider | |
DK160249B (da) | Insekticidt og/eller mitidict virksomme asymmetriske n-substituerede bis-carbamoylsulfidforbindelser, insekticidt og/eller miticidt middel indeholdende disse forbindelser samt framgangsmaade til bekaempelse af insekter og/eller mider | |
DK142876B (da) | Phosphorholdige benzoxazolderivater til anvendelse i insecticider og acaricider. | |
US3318910A (en) | 2-iminothiolanes and related compounds | |
US3101377A (en) | Sulfone derivatives of mercaptohaloethylene | |
US4237168A (en) | N-(4-Chloro-2-methylphenyl)-N-hydroxy methanimidamide and its pesticidal use | |
US3928586A (en) | O,O-Diethyl-0-1-(2,4-dichlorophenyl)-2,2-dibromovinyl phosphate used to control the Colorado potato beetle | |
DE2416054A1 (de) | Verfahren und praeparate zur schaedlingsbekaempfung | |
IL45905A (en) | Thiazole derivatives process for preparing them and insecticidal acaricidal and nematicidal compositions | |
PL116427B1 (en) | Pesticide,in particular insecticide,acaricide and nematocide | |
US3238202A (en) | Amides of o, o-dialkyldithiophos-phorylacetic acids | |
PL136866B1 (en) | Pecticide and process for manufacturing aryl esters of n-oxalyl-n-methylcarbamic acid | |
JP3163545B2 (ja) | 4−チエニル−オキサ(チア)ゾリン誘導体、及びこれを含有する殺虫・殺ダニ剤 | |
US3808333A (en) | O-(2-amino-4-methyl-pyrimidyl-6)-thiophosphoroamidate | |
US4001430A (en) | N-t-Butyl-α-trichlorophenoxybutyramides and their use as mitricides | |
IL23691A (en) | Amidothiolphosphoric acid esters and process for the preparation thereof | |
US2752283A (en) | Phosphorus derivatives, process for their preparation and compositions containing them | |
NO136508B (ja) | ||
US4284626A (en) | O-aryl S-branched alkyl alkylphosphonodithioate insecticides and nematocides | |
US3348940A (en) | Herbicidal and insecticidal composition | |
PL99854B1 (pl) | Sposob wytwarzania nowych pochodnych o-triazolilowych kwasow/tiono/-fosforowych/fosfonowych,fosfinowych/ | |
US3284547A (en) | Phosphoric esters | |
US3034951A (en) | S-[o, o-dialkylphosphorothiomethyl]-s'-alkyltrithiocarbonates and their methods of preparation and use as pesticides | |
RU2036582C1 (ru) | Способ борьбы с вредителями |