DE1214682B - Verfahren zur Herstellung von Dithiophosphonsaeureestern - Google Patents
Verfahren zur Herstellung von DithiophosphonsaeureesternInfo
- Publication number
- DE1214682B DE1214682B DEST22337A DEST022337A DE1214682B DE 1214682 B DE1214682 B DE 1214682B DE ST22337 A DEST22337 A DE ST22337A DE ST022337 A DEST022337 A DE ST022337A DE 1214682 B DE1214682 B DE 1214682B
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- preparation
- acid
- dithiophosphonic acid
- methyl
- 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.)
- Pending
Links
- FLQUDUCNBDGCRI-UHFFFAOYSA-N hydroxy-sulfanyl-sulfidophosphanium Chemical class SP(S)=O FLQUDUCNBDGCRI-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 ester chloride Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- LBKWCYVLTDUGAY-UHFFFAOYSA-N 4-chloro-3-methylbenzenethiol Chemical compound CC1=CC(S)=CC=C1Cl LBKWCYVLTDUGAY-UHFFFAOYSA-N 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000257159 Musca domestica Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 241000591214 Acraea Species 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 241000567413 Estigmene Species 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241001425390 Aphis fabae Species 0.000 description 3
- 241001674044 Blattodea Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 231100001225 mammalian toxicity Toxicity 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 231100000167 toxic agent Toxicity 0.000 description 3
- 239000003440 toxic substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- GFTATZBXSYXGRK-UHFFFAOYSA-N ethyl-hydroxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(O)(S)=S GFTATZBXSYXGRK-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- MHOWCHQNHPCPOE-UHFFFAOYSA-N CCP(O)(OC)=S.Cl Chemical compound CCP(O)(OC)=S.Cl MHOWCHQNHPCPOE-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001480169 Phaseolus maculatus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ILRHGKSQOWBYCL-UHFFFAOYSA-N chloro-ethoxy-ethyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)CC ILRHGKSQOWBYCL-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- OJZGWRZUOHSWMB-UHFFFAOYSA-N ethoxy-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(O)(O)=S OJZGWRZUOHSWMB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001931 phytocidal effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 102220047090 rs6152 Human genes 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A01N57/18—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
- 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
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US292492A US3305610A (en) | 1963-07-02 | 1963-07-02 | Phosphonodithioates as pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1214682B true DE1214682B (de) | 1966-04-21 |
Family
ID=23124910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST22337A Pending DE1214682B (de) | 1963-07-02 | 1964-07-01 | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3305610A (es) |
| BE (1) | BE649880A (es) |
| CH (1) | CH440828A (es) |
| DE (1) | DE1214682B (es) |
| ES (1) | ES301631A1 (es) |
| GB (1) | GB1052991A (es) |
| NL (1) | NL6407466A (es) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138049B (de) * | 1960-02-13 | 1962-10-18 | Bayer Ag | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
| DE1143200B (de) * | 1960-07-21 | 1963-02-07 | Bayer Ag | Verfahren zur Herstellung von Thionophosphonsaeureestern |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
| US3112271A (en) * | 1959-04-13 | 1963-11-26 | Shell Oil Co | Liquid hydrocarbon composition |
| US3095351A (en) * | 1959-08-31 | 1963-06-25 | Monsanto Chemicals | Stabilization of insecticides |
| BE595392A (es) * | 1959-09-24 | |||
| US3149143A (en) * | 1959-12-24 | 1964-09-15 | Monsanto Co | O-ethyl s-(4-chlorophenyl) methylphosphonodithioate |
| AT226253B (de) * | 1960-02-13 | 1963-03-11 | Bayer Ag | Verfahren zur Herstellung von neuen Thionothiolphosphonsäureestern |
| NL267577A (es) * | 1960-07-28 | |||
| US3102900A (en) * | 1962-07-11 | 1963-09-03 | Standard Oil Co | Alkyl phosphonate esters and process for preparing same |
| US3102901A (en) * | 1962-07-24 | 1963-09-03 | Standard Oil Co | Preparation of esters of carboxy-substituted diarylhydroxymethanephosphonic acid |
-
0
- GB GB1052991D patent/GB1052991A/en active Active
-
1963
- 1963-07-02 US US292492A patent/US3305610A/en not_active Expired - Lifetime
-
1964
- 1964-06-29 CH CH850064A patent/CH440828A/de unknown
- 1964-06-29 BE BE649880D patent/BE649880A/xx unknown
- 1964-07-01 NL NL6407466A patent/NL6407466A/xx unknown
- 1964-07-01 DE DEST22337A patent/DE1214682B/de active Pending
- 1964-07-02 ES ES0301631A patent/ES301631A1/es not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138049B (de) * | 1960-02-13 | 1962-10-18 | Bayer Ag | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
| DE1143200B (de) * | 1960-07-21 | 1963-02-07 | Bayer Ag | Verfahren zur Herstellung von Thionophosphonsaeureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1052991A (es) | |
| US3305610A (en) | 1967-02-21 |
| BE649880A (es) | 1964-12-29 |
| ES301631A1 (es) | 1965-05-16 |
| CH440828A (de) | 1967-07-31 |
| NL6407466A (es) | 1965-01-04 |
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