CH566979A5 - (2,5)-Dichloro-(4)-alkyl-mercaptophenyl-thiophosphoric acid - and thiophosphonic acid esters as pesticides - Google Patents
(2,5)-Dichloro-(4)-alkyl-mercaptophenyl-thiophosphoric acid - and thiophosphonic acid esters as pesticidesInfo
- Publication number
- CH566979A5 CH566979A5 CH1440970A CH1440970A CH566979A5 CH 566979 A5 CH566979 A5 CH 566979A5 CH 1440970 A CH1440970 A CH 1440970A CH 1440970 A CH1440970 A CH 1440970A CH 566979 A5 CH566979 A5 CH 566979A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dichloro
- alkyl
- methanol
- mercaptophenol
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims abstract description 4
- 239000002253 acid Substances 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- YGFPFLRARVYKBZ-UHFFFAOYSA-N 2,5-dichloro-4-methylsulfanylphenol Chemical compound CSC1=CC(Cl)=C(O)C=C1Cl YGFPFLRARVYKBZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- SXKBHOQOOGRFJF-UHFFFAOYSA-N 1,2,4-trichloro-5-methoxybenzene Chemical compound COC1=CC(Cl)=C(Cl)C=C1Cl SXKBHOQOOGRFJF-UHFFFAOYSA-N 0.000 claims description 2
- RWDHTEMSFGMSDP-UHFFFAOYSA-N 1,2,4-trichloro-5-methylsulfanylbenzene Chemical compound CSC1=CC(Cl)=C(Cl)C=C1Cl RWDHTEMSFGMSDP-UHFFFAOYSA-N 0.000 claims description 2
- JDAJYNHGBUXIKS-UHFFFAOYSA-N 2,3,4-trichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1Cl JDAJYNHGBUXIKS-UHFFFAOYSA-N 0.000 claims description 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 claims description 2
- SAYWFORZGJPFPO-UHFFFAOYSA-N CC(C)C(C(Cl)=CC(O)=C1Cl)=C1S Chemical compound CC(C)C(C(Cl)=CC(O)=C1Cl)=C1S SAYWFORZGJPFPO-UHFFFAOYSA-N 0.000 claims description 2
- ZWBDFNUGHBEUIL-UHFFFAOYSA-N CCCCC(C(Cl)=CC(O)=C1Cl)=C1S Chemical compound CCCCC(C(Cl)=CC(O)=C1Cl)=C1S ZWBDFNUGHBEUIL-UHFFFAOYSA-N 0.000 claims description 2
- BHXWZXJAJRPIIB-UHFFFAOYSA-N CCSC(C(Cl)=C1)=CC(Cl)=C1O Chemical compound CCSC(C(Cl)=C1)=CC(Cl)=C1O BHXWZXJAJRPIIB-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000000642 acaricide Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- A01N57/06—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 aromatic radicals
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB89951A DE1298990B (de) | 1966-11-22 | 1966-11-22 | O, O-Dialkyl-O-(2, 5-dichlor-4-alkyl-mercapto-phenyl)-thionophosphate und Verfahren zu ihrer Herstellung |
| DEB0093427 | 1967-07-11 | ||
| CH1617767A CH524957A (de) | 1966-11-22 | 1967-11-20 | Schädlingsbekämpfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH566979A5 true CH566979A5 (en) | 1975-09-30 |
Family
ID=27177435
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1440970A CH566979A5 (en) | 1966-11-22 | 1967-11-20 | (2,5)-Dichloro-(4)-alkyl-mercaptophenyl-thiophosphoric acid - and thiophosphonic acid esters as pesticides |
| CH1440870A CH567041A5 (cs) | 1966-11-22 | 1967-11-20 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1440870A CH567041A5 (cs) | 1966-11-22 | 1967-11-20 |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH566979A5 (cs) |
-
1967
- 1967-11-20 CH CH1440970A patent/CH566979A5/de not_active IP Right Cessation
- 1967-11-20 CH CH1440870A patent/CH567041A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH567041A5 (cs) | 1975-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |