US3201444A - Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters - Google Patents
Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters Download PDFInfo
- Publication number
- US3201444A US3201444A US271878A US27187863A US3201444A US 3201444 A US3201444 A US 3201444A US 271878 A US271878 A US 271878A US 27187863 A US27187863 A US 27187863A US 3201444 A US3201444 A US 3201444A
- Authority
- US
- United States
- Prior art keywords
- omicron
- acid
- alkyl
- ester
- cyclohexyl
- 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
- 150000001875 compounds Chemical class 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- 244000078703 ectoparasite Species 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229950005499 carbon tetrachloride Drugs 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- -1 methyLethyl Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010008583 Chloroma Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical class ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07F9/06—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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
Definitions
- R preferably stands for methyLethyl and propyl.
- R preferably stands for cyclohexyl and cyclopentyl.
- R preferably stands for halogen, such as chlorine, bromine and fluorine, methyl, ethyl, methoxy and ethoxy.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF34558A DE1212554B (de) | 1961-07-28 | 1961-07-28 | Verfahren zur Herstellung von kernsubstituierten O, O-Dialkyl-S-phenyl-thiolphosphorsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3201444A true US3201444A (en) | 1965-08-17 |
Family
ID=7095608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US271878A Expired - Lifetime US3201444A (en) | 1961-07-28 | 1963-04-10 | Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3201444A (xx) |
| BE (2) | BE620758A (xx) |
| BR (1) | BR6241516D0 (xx) |
| CH (1) | CH421081A (xx) |
| DE (1) | DE1212554B (xx) |
| DK (1) | DK102941C (xx) |
| GB (2) | GB966057A (xx) |
| NL (3) | NL135595C (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444274A (en) * | 1964-10-29 | 1969-05-13 | Bayer Ag | Asymmetrical para-nitrophenyl phosphates |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4833371B1 (xx) * | 1968-07-19 | 1973-10-13 | ||
| CH516598A (de) * | 1969-04-28 | 1971-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von Dithiophosphorsäureestern |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2690450A (en) * | 1951-03-23 | 1954-09-28 | Allied Chem & Dye Corp | Method for preparation of sulfur-containing esters of phosphoric acid |
| US2861876A (en) * | 1955-12-01 | 1958-11-25 | Monsanto Chemicals | Method of destroying undesired plants |
| US2962518A (en) * | 1957-09-28 | 1960-11-29 | Bayer Ag | Phosphonic acid esters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR994479A (fr) * | 1949-07-10 | 1951-11-16 | S-nitrophényl-0, 0-dialkylthiolphosphates et procédé pour les obtenir | |
| DE817057C (de) * | 1949-10-11 | 1951-10-15 | Bayer Ag | Schaedlingsbekaempfungsmittel |
| US2897227A (en) * | 1956-04-04 | 1959-07-28 | Dow Chemical Co | S-(chlorophenyl) o,o-dialkyl phosphorodithioates |
-
0
- BE BE620621D patent/BE620621A/xx unknown
- BE BE620758D patent/BE620758A/xx unknown
- NL NL281501D patent/NL281501A/xx unknown
- NL NL281500D patent/NL281500A/xx unknown
- NL NL135595D patent/NL135595C/xx active
-
1961
- 1961-07-28 DE DEF34558A patent/DE1212554B/de active Pending
-
1962
- 1962-07-06 CH CH814862A patent/CH421081A/de unknown
- 1962-07-26 DK DK332962AA patent/DK102941C/da active
- 1962-07-27 BR BR141516/62A patent/BR6241516D0/pt unknown
- 1962-07-27 GB GB29057/62A patent/GB966057A/en not_active Expired
- 1962-07-30 GB GB29262/62A patent/GB983886A/en not_active Expired
-
1963
- 1963-04-10 US US271878A patent/US3201444A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2690450A (en) * | 1951-03-23 | 1954-09-28 | Allied Chem & Dye Corp | Method for preparation of sulfur-containing esters of phosphoric acid |
| US2861876A (en) * | 1955-12-01 | 1958-11-25 | Monsanto Chemicals | Method of destroying undesired plants |
| US2962518A (en) * | 1957-09-28 | 1960-11-29 | Bayer Ag | Phosphonic acid esters |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444274A (en) * | 1964-10-29 | 1969-05-13 | Bayer Ag | Asymmetrical para-nitrophenyl phosphates |
Also Published As
| Publication number | Publication date |
|---|---|
| DK102941C (da) | 1965-10-25 |
| NL281501A (xx) | |
| NL135595C (xx) | |
| BR6241516D0 (pt) | 1973-05-24 |
| DE1212554B (de) | 1966-03-17 |
| NL281500A (xx) | |
| GB983886A (en) | 1965-02-17 |
| GB966057A (en) | 1964-08-06 |
| BE620621A (xx) | |
| CH421081A (de) | 1966-09-30 |
| BE620758A (xx) |
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