DE1184759B - Verfahren zur Herstellung von als Schaedlingsbekaempfungsmittel geeigneten neuen Chlormethylthionothiolphosphonsaeureestern - Google Patents
Verfahren zur Herstellung von als Schaedlingsbekaempfungsmittel geeigneten neuen ChlormethylthionothiolphosphonsaeureesternInfo
- Publication number
- DE1184759B DE1184759B DEST20283A DEST020283A DE1184759B DE 1184759 B DE1184759 B DE 1184759B DE ST20283 A DEST20283 A DE ST20283A DE ST020283 A DEST020283 A DE ST020283A DE 1184759 B DE1184759 B DE 1184759B
- Authority
- DE
- Germany
- Prior art keywords
- chloromethylthionothiolphosphonic
- general formula
- new
- acid esters
- clch
- 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
- 238000000034 method Methods 0.000 title claims description 8
- CBCSSOAYVLXXOR-UHFFFAOYSA-N [3-(chloromethyl)-1-sulfanylidenethiophen-2-yl]phosphonic acid Chemical class ClCC1=C(S(C=C1)=S)P(O)(=O)O CBCSSOAYVLXXOR-UHFFFAOYSA-N 0.000 title claims description 4
- 241000607479 Yersinia pestis Species 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 n-propyloxy Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KFUVAAKGERCXGZ-UHFFFAOYSA-N chloromethyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)CCl KFUVAAKGERCXGZ-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000258913 Oncopeltus fasciatus Species 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 241000238657 Blattella germanica Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- YAESYRWEEVNLOA-UHFFFAOYSA-N 4-chloro-2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1S YAESYRWEEVNLOA-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000567412 Estigmene acrea Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 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
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
- C07F9/28—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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- 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 |
|---|---|---|---|
| US17289062A | 1962-02-13 | 1962-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1184759B true DE1184759B (de) | 1965-01-07 |
Family
ID=22629624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST20283A Pending DE1184759B (de) | 1962-02-13 | 1963-02-12 | Verfahren zur Herstellung von als Schaedlingsbekaempfungsmittel geeigneten neuen Chlormethylthionothiolphosphonsaeureestern |
Country Status (6)
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714100A (en) * | 1952-08-05 | 1955-07-26 | Victor Chemical Works | Diallyl monochloromethanephosphonate and polymers |
| US2841604A (en) * | 1954-08-23 | 1958-07-01 | Victor Chemical Works | Dialkyl monochloromethanephosphonate esters containing from 3 to 10 carbon atoms in the hydrocarbon radicals |
| US2863903A (en) * | 1954-10-07 | 1958-12-09 | Victor Chemical Works | Alkyl aryl monochloromethane-phosphonate esters |
| US2900405A (en) * | 1953-05-29 | 1959-08-18 | Eastman Kodak Co | Halomethanephosphonates |
| US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
| US2922810A (en) * | 1953-07-13 | 1960-01-26 | Victor Chemical Works | Chloromethanephosphonic acid esters |
| US2927014A (en) * | 1957-02-14 | 1960-03-01 | Virginia Carolina Chem Corp | Method for killing plants |
| US2960522A (en) * | 1954-10-07 | 1960-11-15 | Victor Chemical Works | Dicresyl monochloromethane-phosphonate |
| US2988474A (en) * | 1960-07-28 | 1961-06-13 | Stauffer Chemical Co | Novel insecticides, acaricides and nematocides |
| US2988565A (en) * | 1958-11-14 | 1961-06-13 | Victor Chemical Works | O-ethyl-o-ethylmercaptoethyl chloromethylthionophosphonate |
| FR1266440A (fr) * | 1960-09-03 | 1961-07-07 | Stauffer Chemical Co | Nouveaux thio-phosphonates, actifs en particulier comme acaricides et insecticides |
| FR1280984A (fr) * | 1960-02-13 | 1962-01-08 | Bayer Ag | Esters dithiophosphoniques et leur procédé de préparation |
-
0
- NL NL288842D patent/NL288842A/xx unknown
- BE BE628296D patent/BE628296A/xx unknown
-
1963
- 1963-01-31 GB GB4033/63A patent/GB1034185A/en not_active Expired
- 1963-02-11 CH CH167263A patent/CH465320A/de unknown
- 1963-02-12 DE DEST20283A patent/DE1184759B/de active Pending
- 1963-02-12 NL NL63288842A patent/NL139651B/xx unknown
- 1963-02-13 FR FR924589A patent/FR1348127A/fr not_active Expired
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714100A (en) * | 1952-08-05 | 1955-07-26 | Victor Chemical Works | Diallyl monochloromethanephosphonate and polymers |
| US2900405A (en) * | 1953-05-29 | 1959-08-18 | Eastman Kodak Co | Halomethanephosphonates |
| US2922810A (en) * | 1953-07-13 | 1960-01-26 | Victor Chemical Works | Chloromethanephosphonic acid esters |
| US2841604A (en) * | 1954-08-23 | 1958-07-01 | Victor Chemical Works | Dialkyl monochloromethanephosphonate esters containing from 3 to 10 carbon atoms in the hydrocarbon radicals |
| US2863903A (en) * | 1954-10-07 | 1958-12-09 | Victor Chemical Works | Alkyl aryl monochloromethane-phosphonate esters |
| US2960522A (en) * | 1954-10-07 | 1960-11-15 | Victor Chemical Works | Dicresyl monochloromethane-phosphonate |
| US2927014A (en) * | 1957-02-14 | 1960-03-01 | Virginia Carolina Chem Corp | Method for killing plants |
| US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
| US2988565A (en) * | 1958-11-14 | 1961-06-13 | Victor Chemical Works | O-ethyl-o-ethylmercaptoethyl chloromethylthionophosphonate |
| FR1280984A (fr) * | 1960-02-13 | 1962-01-08 | Bayer Ag | Esters dithiophosphoniques et leur procédé de préparation |
| US2988474A (en) * | 1960-07-28 | 1961-06-13 | Stauffer Chemical Co | Novel insecticides, acaricides and nematocides |
| FR1266440A (fr) * | 1960-09-03 | 1961-07-07 | Stauffer Chemical Co | Nouveaux thio-phosphonates, actifs en particulier comme acaricides et insecticides |
Also Published As
| Publication number | Publication date |
|---|---|
| BE628296A (US20100056889A1-20100304-C00004.png) | |
| FR1348127A (fr) | 1964-01-04 |
| CH465320A (de) | 1968-11-15 |
| NL288842A (US20100056889A1-20100304-C00004.png) | |
| GB1034185A (en) | 1966-06-29 |
| NL139651B (nl) | 1973-09-17 |
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