NO784274L - Fosforsyre- og thiofosforsyreestere av 5(3)-hydroxy-pyrazoler med insecticid virkning - Google Patents
Fosforsyre- og thiofosforsyreestere av 5(3)-hydroxy-pyrazoler med insecticid virkningInfo
- Publication number
- NO784274L NO784274L NO784274A NO784274A NO784274L NO 784274 L NO784274 L NO 784274L NO 784274 A NO784274 A NO 784274A NO 784274 A NO784274 A NO 784274A NO 784274 L NO784274 L NO 784274L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxypyrazole
- formula
- chloro
- thiophosphoric acid
- phenyl
- Prior art date
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 5
- 230000000749 insecticidal effect Effects 0.000 title description 3
- 239000002253 acid Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 32
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 150000003580 thiophosphoric acid esters Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 241000238631 Hexapoda Species 0.000 claims description 9
- -1 1-isopropyl-3-bromo-5-hydroxypyrazole Chemical compound 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 6
- 241000244206 Nematoda Species 0.000 claims description 6
- QGLOLKPCOMUAJX-UHFFFAOYSA-N OC1=CC(Cl)=NN1C1=CC=CC=C1 Chemical compound OC1=CC(Cl)=NN1C1=CC=CC=C1 QGLOLKPCOMUAJX-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- AQHAWPBZGWMFAS-UHFFFAOYSA-N CC(C)N1N=C(Cl)C=C1O Chemical compound CC(C)N1N=C(Cl)C=C1O AQHAWPBZGWMFAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- BOGSOFADOWIECK-UHFFFAOYSA-N [N].C=1C=NNC=1 Chemical group [N].C=1C=NNC=1 BOGSOFADOWIECK-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- CPTNHQNQINTDNG-UHFFFAOYSA-N CCN1N=C(Cl)C=C1O Chemical compound CCN1N=C(Cl)C=C1O CPTNHQNQINTDNG-UHFFFAOYSA-N 0.000 claims 3
- CDSAPDHBCYSHAQ-UHFFFAOYSA-N ethoxy-hydroxy-methylperoxy-sulfanylidene-lambda5-phosphane Chemical compound COOP(OCC)(O)=S CDSAPDHBCYSHAQ-UHFFFAOYSA-N 0.000 claims 3
- XZADCKOQSTXYSC-UHFFFAOYSA-N 3-chloro-2-(4-nitrophenyl)-1h-pyrazol-5-one Chemical compound N1=C(O)C=C(Cl)N1C1=CC=C([N+]([O-])=O)C=C1 XZADCKOQSTXYSC-UHFFFAOYSA-N 0.000 claims 2
- YWSVEGWUIUAOJF-UHFFFAOYSA-N CN1N=C(Cl)C=C1O Chemical compound CN1N=C(Cl)C=C1O YWSVEGWUIUAOJF-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- BEYRFIRGLRBHHX-UHFFFAOYSA-N OC1=CC(Cl)=NN1CC1=CC=CC=C1 Chemical compound OC1=CC(Cl)=NN1CC1=CC=CC=C1 BEYRFIRGLRBHHX-UHFFFAOYSA-N 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000004071 biological effect Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003217 pyrazoles Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000256059 Culex pipiens Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- VAWGHWUJVWHUKW-UHFFFAOYSA-N 3,3-dichloroprop-2-enoyl chloride Chemical compound ClC(Cl)=CC(Cl)=O VAWGHWUJVWHUKW-UHFFFAOYSA-N 0.000 description 1
- TUUGFLAHJMHZFV-UHFFFAOYSA-N 3-hydroxy-2-phenyl-1h-pyrazol-5-one Chemical compound OC1=CC(=O)NN1C1=CC=CC=C1 TUUGFLAHJMHZFV-UHFFFAOYSA-N 0.000 description 1
- 241000238659 Blatta Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000258915 Leptinotarsa Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- PKUWKAXTAVNIJR-UHFFFAOYSA-N O,O-diethyl hydrogen thiophosphate Chemical compound CCOP(O)(=S)OCC PKUWKAXTAVNIJR-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 229920005439 Perspex® Polymers 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- AVKHCKXGKPAGEI-UHFFFAOYSA-N Phenicarbazide Chemical compound NC(=O)NNC1=CC=CC=C1 AVKHCKXGKPAGEI-UHFFFAOYSA-N 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- GLEPDFWPHDUTMJ-UHFFFAOYSA-N ethyl n-(propan-2-ylamino)carbamate Chemical compound CCOC(=O)NNC(C)C GLEPDFWPHDUTMJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable 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
- 230000000977 initiatory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000520 microinjection Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- A01N57/02—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
- A01N57/08—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 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3119177A IT1090365B (it) | 1977-12-23 | 1977-12-23 | 5(3)-idrossi-pirazoli sostituiti in posizione 3(5) e loro procedimento di preparazione |
| IT31190/77A IT1090364B (it) | 1977-12-23 | 1977-12-23 | Esteri fosforici e tiofosforici di 5(3) idrossipirazoli sostituiti in posizione 3(5) insetticidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO784274L true NO784274L (no) | 1979-06-26 |
Family
ID=26328917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO784274A NO784274L (no) | 1977-12-23 | 1978-12-19 | Fosforsyre- og thiofosforsyreestere av 5(3)-hydroxy-pyrazoler med insecticid virkning |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US4256902A (de) |
| JP (1) | JPS5495567A (de) |
| AR (1) | AR223157A1 (de) |
| AU (1) | AU4276578A (de) |
| BR (1) | BR7808414A (de) |
| CA (1) | CA1113946A (de) |
| CH (1) | CH639393A5 (de) |
| CS (1) | CS207749B2 (de) |
| DD (3) | DD150062A5 (de) |
| DE (2) | DE2858748C2 (de) |
| DK (1) | DK569478A (de) |
| EG (1) | EG13746A (de) |
| ES (1) | ES476263A1 (de) |
| GB (1) | GB2013182B (de) |
| GR (1) | GR71657B (de) |
| IL (1) | IL56259A (de) |
| IN (1) | IN149776B (de) |
| LU (1) | LU80702A1 (de) |
| NL (1) | NL7812293A (de) |
| NO (1) | NO784274L (de) |
| NZ (1) | NZ189284A (de) |
| OA (1) | OA06140A (de) |
| PL (1) | PL115092B1 (de) |
| PT (1) | PT68967A (de) |
| RO (2) | RO77326A (de) |
| SU (2) | SU1071197A3 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2604174B1 (fr) * | 1986-09-18 | 1989-06-02 | Roussel Uclaf | Nouveaux derives de la 5-pyrazolone, leur procede de preparation et leur utilisation comme herbicides |
| US4855442A (en) * | 1988-04-13 | 1989-08-08 | Monsanto Company | Substituted 3-hydroxy pyrazoles |
| DE3931303A1 (de) * | 1989-09-20 | 1991-03-28 | Desowag Materialschutz Gmbh | Verfahren zum vorbeugenden materialschutz gegenueber staendig und/oder temporaer im boden lebenden schaedlingen, insbesondere termiten |
| DE4315384A1 (de) * | 1992-09-03 | 1994-03-10 | Bayer Ag | Phosphoryloxypyrazolderivate |
| WO2000031041A2 (de) * | 1998-11-19 | 2000-06-02 | Basf Aktiengesellschaft | Verfahren zur herstellung von 1-substituierten 5-hydroxypyrazolen |
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439098A (en) * | 1944-12-22 | 1948-04-06 | Eastman Kodak Co | Alkoxy pyrazolone couplers |
| AT184580B (de) * | 1951-04-20 | 1956-02-10 | Geigy Ag J R | Verfahren zur Herstellung neuer, heterocyclischer Phosphorsäure- bzw. Thiophosphorsäureester |
| CH436835A (de) * | 1959-03-06 | 1967-05-31 | Philips Nv | Schädlingsbekämpfungsmittel |
| US3166475A (en) * | 1959-12-29 | 1965-01-19 | Fiordalisi Fernanda Misani | Anti-convulsant pyrazolones |
| US3644374A (en) * | 1969-04-04 | 1972-02-22 | Raoul Buijle | Process for the preparation of acylated amides |
| DE2037853C3 (de) * | 1970-07-30 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Pyrazole- (thiono)-phosphor(phosphon)saureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| DE2060198A1 (de) * | 1970-12-08 | 1972-06-15 | Bayer Ag | Pyrazolo-(thiono)-phosphor(phosphon)-saeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| BE785785A (fr) * | 1971-07-02 | 1973-01-03 | Bayer Ag | Nouveaux esters d'acides o-pyrazolothiono-phosphoriques (phosphoniques), leur preparation et leur application comme insecticides et acaricide |
| DE2219484A1 (de) * | 1972-04-21 | 1973-10-31 | Bayer Ag | 0-pyrazolo(thiono)-phosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DD108536A1 (de) * | 1972-12-21 | 1974-09-20 | ||
| DE2608643A1 (de) * | 1976-03-03 | 1977-09-08 | Bayer Ag | O,s-dialkyl-o-pyrazoldithiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2639258A1 (de) * | 1976-09-01 | 1978-03-02 | Bayer Ag | Tert.-butyl-substituierte pyrazolyl (thiono)(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| JPS5547695A (en) * | 1978-09-19 | 1980-04-04 | Takeda Chem Ind Ltd | Pyrazole phosphate, its preparation, and insecticide and miticide |
-
1978
- 1978-12-19 NL NL7812293A patent/NL7812293A/xx not_active Application Discontinuation
- 1978-12-19 DK DK569478A patent/DK569478A/da not_active Application Discontinuation
- 1978-12-19 NO NO784274A patent/NO784274L/no unknown
- 1978-12-20 CH CH1298278A patent/CH639393A5/it not_active IP Right Cessation
- 1978-12-20 RO RO7895990A patent/RO77326A/ro unknown
- 1978-12-20 RO RO102780A patent/RO81226B/ro unknown
- 1978-12-20 PL PL1978211969A patent/PL115092B1/pl unknown
- 1978-12-20 EG EG728/78A patent/EG13746A/xx active
- 1978-12-20 AR AR274881A patent/AR223157A1/es active
- 1978-12-20 IL IL56259A patent/IL56259A/xx unknown
- 1978-12-21 NZ NZ189284A patent/NZ189284A/xx unknown
- 1978-12-21 DE DE2858748A patent/DE2858748C2/de not_active Expired - Fee Related
- 1978-12-21 BR BR7808414A patent/BR7808414A/pt unknown
- 1978-12-21 DE DE19782855256 patent/DE2855256A1/de active Granted
- 1978-12-21 AU AU42765/78A patent/AU4276578A/en active Pending
- 1978-12-21 IN IN1358/CAL/78A patent/IN149776B/en unknown
- 1978-12-21 GB GB7849730A patent/GB2013182B/en not_active Expired
- 1978-12-21 CS CS788758A patent/CS207749B2/cs unknown
- 1978-12-21 GR GR57957A patent/GR71657B/el unknown
- 1978-12-22 DD DD78220135A patent/DD150062A5/de unknown
- 1978-12-22 LU LU80702A patent/LU80702A1/xx unknown
- 1978-12-22 PT PT68967A patent/PT68967A/pt unknown
- 1978-12-22 DD DD78210125A patent/DD150425A5/de unknown
- 1978-12-22 ES ES476263A patent/ES476263A1/es not_active Expired
- 1978-12-22 JP JP15769878A patent/JPS5495567A/ja active Granted
- 1978-12-22 DD DD78220132A patent/DD150056A5/de unknown
- 1978-12-22 SU SU782699555A patent/SU1071197A3/ru active
- 1978-12-22 OA OA56696A patent/OA06140A/xx unknown
- 1978-12-22 CA CA318,485A patent/CA1113946A/en not_active Expired
-
1979
- 1979-06-18 SU SU792776759A patent/SU1001858A3/ru active
-
1980
- 1980-03-12 US US06/129,724 patent/US4256902A/en not_active Expired - Lifetime
-
1982
- 1982-09-29 US US06/426,881 patent/US4459294A/en not_active Expired - Fee Related
-
1983
- 1983-08-18 US US06/524,229 patent/US4492690A/en not_active Expired - Fee Related
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