DE1122935B - Verfahren zur Herstellung von akariciden Dithiophosphorsaeureestern - Google Patents
Verfahren zur Herstellung von akariciden DithiophosphorsaeureesternInfo
- Publication number
- DE1122935B DE1122935B DES67422A DES0067422A DE1122935B DE 1122935 B DE1122935 B DE 1122935B DE S67422 A DES67422 A DE S67422A DE S0067422 A DES0067422 A DE S0067422A DE 1122935 B DE1122935 B DE 1122935B
- Authority
- DE
- Germany
- Prior art keywords
- acaricidal
- acid esters
- dithiophosphoric acid
- compound
- formula
- 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
- 230000000895 acaricidal effect Effects 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003921 oil Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- ATBPGPNOOVIFLN-UHFFFAOYSA-N azanium;methoxy-methylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [NH4+].COP([O-])(=S)SC ATBPGPNOOVIFLN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 239000003415 peat Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- MSXGQMLWJUMPOJ-UHFFFAOYSA-N C(C)OP(S)(OCC)=S.[Na] Chemical compound C(C)OP(S)(OCC)=S.[Na] MSXGQMLWJUMPOJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000118205 Ovicides Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000158927 Scolochloa Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HFRHTRKMBOQLLL-UHFFFAOYSA-N azane;diethoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [NH4+].CCOP([S-])(=S)OCC HFRHTRKMBOQLLL-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray 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
- A01N57/10—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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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 |
|---|---|---|---|
| CH7062159A CH372040A (de) | 1959-03-10 | 1959-03-10 | Verfahren zur Herstellung neuer Dithiophosphorsäureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1122935B true DE1122935B (de) | 1962-02-01 |
Family
ID=4530397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES67422A Pending DE1122935B (de) | 1959-03-10 | 1960-03-04 | Verfahren zur Herstellung von akariciden Dithiophosphorsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3032466A (enEXAMPLES) |
| BE (1) | BE588516A (enEXAMPLES) |
| CH (1) | CH372040A (enEXAMPLES) |
| DE (1) | DE1122935B (enEXAMPLES) |
| FR (1) | FR1250948A (enEXAMPLES) |
| GB (1) | GB944840A (enEXAMPLES) |
| NL (2) | NL249142A (enEXAMPLES) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2604224A1 (de) * | 1976-02-04 | 1977-08-11 | Hoechst Ag | Herbizide mittel |
| EP0012172A1 (de) * | 1978-10-25 | 1980-06-25 | Bayer Ag | O-Äthyl-S-n-propyl-dithiophosphoryloxy-essigsäure-N-methylanilid, Verfahren zu seiner Herstellung sowie seine Verwendung als Herbizid |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3102019A (en) * | 1961-08-16 | 1963-08-27 | Monsanto Chemicals | Method for inhibiting germination and preemergent growth of plants using s(n-aryl, n-aliphatic carbamoylmethyl) phosphorothiate triesters |
| DE2617736C2 (de) * | 1976-04-23 | 1982-12-09 | Hoechst Ag, 6000 Frankfurt | Schädlingsbekämpfungsmittel |
| NL7700930A (nl) * | 1976-02-04 | 1977-08-08 | Hoechst Ag | Plantenbeschermingsmiddel. |
| GB2004187B (en) * | 1977-09-14 | 1982-05-26 | Ici Australia Ltd | Insecticides |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2325331A (en) * | 1935-12-23 | 1943-07-27 | Firm J R Geigy S A | Amino-acid amide derivatives and a process for their manufacture |
| US2139190A (en) * | 1935-12-23 | 1938-12-06 | Firm J R Geigy S A | Amino-acid derivatives and their manufacture |
| US2343071A (en) * | 1937-07-14 | 1944-02-29 | Firm Of J R Geigy A G | Amino fatty acid derivatives and their manufacture |
| CA494562A (en) * | 1948-02-04 | 1953-07-21 | American Cyanamid Company | Carbamylalkyl phosphates and method of preparation |
| US2752393A (en) * | 1950-04-21 | 1956-06-26 | Variapat Ag | Trifluoromethyl-imino-bisacetanilide ammonium salts |
| FR1193017A (fr) * | 1958-01-28 | 1959-10-29 | Rhone Poulenc Sa | Nouveaux esters phosphoriques renfermant une fonction amide, leur préparation et leurs emplois |
| DE3107707C2 (de) * | 1981-02-28 | 1983-04-21 | Spezial - Papiermaschinenfabrik August Alfred Krupp GmbH + Co Hilden bei Düsseldorf, 4010 Hilden | Druckempfindliches Aufzeichnungsmaterial, Verfahren zu dessen Herstellung und Durchschreibesatz |
-
0
- NL NL120555D patent/NL120555C/xx active
- NL NL249142D patent/NL249142A/xx unknown
-
1959
- 1959-03-10 CH CH7062159A patent/CH372040A/de unknown
-
1960
- 1960-02-12 GB GB5142/60A patent/GB944840A/en not_active Expired
- 1960-03-01 US US11995A patent/US3032466A/en not_active Expired - Lifetime
- 1960-03-04 DE DES67422A patent/DE1122935B/de active Pending
- 1960-03-08 FR FR820740A patent/FR1250948A/fr not_active Expired
- 1960-03-10 BE BE588516A patent/BE588516A/fr unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2604224A1 (de) * | 1976-02-04 | 1977-08-11 | Hoechst Ag | Herbizide mittel |
| FR2340047A1 (fr) * | 1976-02-04 | 1977-09-02 | Hoechst Ag | Produits herbicides a base de composes organophosphores |
| US4278461A (en) | 1976-02-04 | 1981-07-14 | Hoechst Aktiengesellschaft | Herbicidal agents |
| EP0012172A1 (de) * | 1978-10-25 | 1980-06-25 | Bayer Ag | O-Äthyl-S-n-propyl-dithiophosphoryloxy-essigsäure-N-methylanilid, Verfahren zu seiner Herstellung sowie seine Verwendung als Herbizid |
Also Published As
| Publication number | Publication date |
|---|---|
| GB944840A (en) | 1963-12-18 |
| FR1250948A (fr) | 1961-01-13 |
| CH372040A (de) | 1963-09-30 |
| BE588516A (fr) | 1960-09-12 |
| NL120555C (enEXAMPLES) | |
| NL249142A (enEXAMPLES) | |
| US3032466A (en) | 1962-05-01 |
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