PL93830B1 - Thiazoltriazolylphosphonothioates[au6760774a] - Google Patents
Thiazoltriazolylphosphonothioates[au6760774a] Download PDFInfo
- Publication number
- PL93830B1 PL93830B1 PL1974184804A PL18480474A PL93830B1 PL 93830 B1 PL93830 B1 PL 93830B1 PL 1974184804 A PL1974184804 A PL 1974184804A PL 18480474 A PL18480474 A PL 18480474A PL 93830 B1 PL93830 B1 PL 93830B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- solvent
- ethyl
- triazolyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 7
- 230000000895 acaricidal effect Effects 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000000749 insecticidal effect Effects 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000012442 inert solvent Substances 0.000 abstract description 4
- -1 alkali metal salt Chemical class 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 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 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 abstract 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 241000251468 Actinopterygii Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- LCAHOBIZRHFQAC-UHFFFAOYSA-N 6-bromo-5-ethyl-1h-[1,3]thiazolo[3,2-b][1,2,4]triazol-2-one Chemical compound OC1=NN2C(Br)=C(CC)SC2=N1 LCAHOBIZRHFQAC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RLYUNPNLXMSXAX-UHFFFAOYSA-N 5-methylthiazole Chemical compound CC1=CN=CS1 RLYUNPNLXMSXAX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000252233 Cyprinus carpio Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100001252 long-term toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48039714A JPS49125536A (xx) | 1973-04-07 | 1973-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL93830B1 true PL93830B1 (en) | 1977-06-30 |
Family
ID=12560646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974184804A PL93830B1 (en) | 1973-04-07 | 1974-04-06 | Thiazoltriazolylphosphonothioates[au6760774a] |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS49125536A (xx) |
| AR (1) | AR204827A1 (xx) |
| AT (1) | AT325059B (xx) |
| AU (1) | AU458910B2 (xx) |
| BE (1) | BE804324A (xx) |
| BR (1) | BR7402381D0 (xx) |
| CS (1) | CS174237B2 (xx) |
| DD (2) | DD113011A5 (xx) |
| EG (1) | EG11323A (xx) |
| ES (1) | ES425046A1 (xx) |
| FR (1) | FR2224482B1 (xx) |
| GB (1) | GB1389692A (xx) |
| HU (1) | HU168088B (xx) |
| IL (1) | IL44343A (xx) |
| IT (1) | IT988234B (xx) |
| KE (1) | KE2581A (xx) |
| MY (1) | MY7600050A (xx) |
| NL (1) | NL7404708A (xx) |
| PL (1) | PL93830B1 (xx) |
| TR (1) | TR17687A (xx) |
-
1973
- 1973-04-07 JP JP48039714A patent/JPS49125536A/ja active Pending
- 1973-04-24 GB GB3020873*A patent/GB1389692A/en not_active Expired
- 1973-06-11 IT IT50615/73A patent/IT988234B/it active
- 1973-08-31 BE BE135207A patent/BE804324A/xx unknown
-
1974
- 1974-01-01 AR AR253162A patent/AR204827A1/es active
- 1974-03-04 IL IL44343A patent/IL44343A/xx unknown
- 1974-03-26 BR BR2381/74A patent/BR7402381D0/pt unknown
- 1974-03-29 FR FR7411334A patent/FR2224482B1/fr not_active Expired
- 1974-04-04 AT AT282974A patent/AT325059B/de not_active IP Right Cessation
- 1974-04-05 CS CS2479A patent/CS174237B2/cs unknown
- 1974-04-05 AU AU67607/74A patent/AU458910B2/en not_active Expired
- 1974-04-05 ES ES425046A patent/ES425046A1/es not_active Expired
- 1974-04-05 TR TR17687A patent/TR17687A/xx unknown
- 1974-04-05 NL NL7404708A patent/NL7404708A/xx unknown
- 1974-04-05 DD DD177734A patent/DD113011A5/xx unknown
- 1974-04-05 DD DD184822A patent/DD116133A5/xx unknown
- 1974-04-06 PL PL1974184804A patent/PL93830B1/pl unknown
- 1974-04-07 HU HUNI175A patent/HU168088B/hu unknown
- 1974-04-07 EG EG102/74A patent/EG11323A/xx active
-
1975
- 1975-11-18 KE KE2581*UA patent/KE2581A/xx unknown
-
1976
- 1976-12-30 MY MY50/76A patent/MY7600050A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT325059B (de) | 1975-10-10 |
| FR2224482B1 (xx) | 1977-10-14 |
| IL44343A (en) | 1976-09-30 |
| MY7600050A (en) | 1976-12-31 |
| IL44343A0 (en) | 1974-06-30 |
| CS174237B2 (xx) | 1977-03-31 |
| JPS49125536A (xx) | 1974-12-02 |
| KE2581A (en) | 1975-12-11 |
| ES425046A1 (es) | 1976-11-16 |
| DE2323720B2 (de) | 1976-05-20 |
| AU458910B2 (en) | 1975-03-13 |
| DE2323720A1 (de) | 1974-10-17 |
| DD116133A5 (xx) | 1975-11-12 |
| BR7402381D0 (pt) | 1974-11-26 |
| FR2224482A1 (xx) | 1974-10-31 |
| GB1389692A (en) | 1975-04-03 |
| TR17687A (tr) | 1975-07-23 |
| EG11323A (en) | 1977-03-31 |
| DD113011A5 (xx) | 1975-05-12 |
| NL7404708A (xx) | 1974-10-09 |
| IT988234B (it) | 1975-04-10 |
| AR204827A1 (es) | 1976-03-05 |
| AU6760774A (en) | 1975-03-13 |
| HU168088B (xx) | 1976-02-28 |
| BE804324A (fr) | 1973-12-17 |
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