DE2637007A1 - Isoxazolyl(thiono) (thiol)-phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide - Google Patents
Isoxazolyl(thiono) (thiol)-phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizideInfo
- Publication number
- DE2637007A1 DE2637007A1 DE19762637007 DE2637007A DE2637007A1 DE 2637007 A1 DE2637007 A1 DE 2637007A1 DE 19762637007 DE19762637007 DE 19762637007 DE 2637007 A DE2637007 A DE 2637007A DE 2637007 A1 DE2637007 A1 DE 2637007A1
- Authority
- DE
- Germany
- Prior art keywords
- spp
- tert
- butyl
- thiono
- iso
- 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
- -1 ISOXAZOLYL (THIONO) Chemical class 0.000 title claims description 36
- 150000003573 thiols Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 239000002917 insecticide Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
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- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- VEAVRDCRZPVBLF-UHFFFAOYSA-N CC(C)(C)C=1C=C(O)ON=1 Chemical class CC(C)(C)C=1C=C(O)ON=1 VEAVRDCRZPVBLF-UHFFFAOYSA-N 0.000 claims description 5
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- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- JRVYNNNVVQCNTG-UHFFFAOYSA-N ethoxy-(6-sulfanylidenecyclohexa-2,4-dien-1-yl)phosphinic acid Chemical compound CCOP(O)(=O)C1C=CC=CC1=S JRVYNNNVVQCNTG-UHFFFAOYSA-N 0.000 description 1
- VUYNTIDSHCJIKF-UHFFFAOYSA-N ethyl 4,4-dimethyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)(C)C VUYNTIDSHCJIKF-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
-
- 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
- A01N57/08—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 heterocyclic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762637007 DE2637007A1 (de) | 1976-08-17 | 1976-08-17 | Isoxazolyl(thiono) (thiol)-phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| PT66913A PT66913B (de) | 1976-08-17 | 1977-08-12 | Isoxazolyl(thiono)(thiol)-phosphor-saureester bzw.-esteramide verfahren zu ihrer herstellung und ihre verwendung alsinsektizide |
| JP9709377A JPS5323968A (en) | 1976-08-17 | 1977-08-15 | Novel isoxazolyl*thiono**thiol**phosphate *phosphonate* esters and esterramides and its use as insecticide |
| IL52735A IL52735A0 (en) | 1976-08-17 | 1977-08-15 | Novel esters and ester-amides of phosphoric and phosphonic acids and of their mono- and dithio-analogues their preparation and their use as insecticides |
| BR7705411A BR7705411A (pt) | 1976-08-17 | 1977-08-16 | Processo para a preparacao de esteres ou esteramidas do acido isoxazolil(tiono)(tiol)-fosforico(fosfonico)e composicoes inseticidas a base destes |
| DK364377A DK364377A (da) | 1976-08-17 | 1977-08-16 | Isoxaxolyl-(thiono)(thiol)-phosphor (phosphon)-syreestere eller-esteramider fremgangsmaade til deres fremstilling og deres anvendelse som insecticider |
| FR7725045A FR2362153A1 (fr) | 1976-08-17 | 1977-08-16 | Nouveaux esters et amides d'esters d'isoxazolyle d'acide (thiono) (thiol)-phosphorique (phosphonique), leur procede de preparation et leur application comme insecticides |
| ZA00774940A ZA774940B (en) | 1976-08-17 | 1977-08-16 | Novel isoxazolyl(thiono)(thiol)-phosphoric(phosphonic)acid esters and esteramides and their use as insecticides |
| ES461622A ES461622A1 (es) | 1976-08-17 | 1977-08-16 | Procedimiento para preparar esteres y amidas de esteres de acidos isoxazolil (tiono) (tiol)-fosforicos (fosfonicos). |
| NL7709038A NL7709038A (nl) | 1976-08-17 | 1977-08-16 | Isoxazolyl(thiono)(thiol)-fosfor(fosfon)-zuur- esters respectievelijk -esteramiden, werkwijze voor het bereiden ervan alsmede de toepassing ervan als insecticide. |
| SE7709226A SE7709226L (sv) | 1976-08-17 | 1977-08-16 | Isoxazolyl(tiono)(tiol)-fosfor(fosfon)-syraestrar och -esteramider till anvendning som insekticider och sett att framstella foreningarna |
| PL20029977A PL200299A1 (pl) | 1976-08-17 | 1977-08-16 | Srodek owadobojczy oraz sposob wytwarzania estrow wzglednie amidow estrow izoksazolilozowych kwasow(tiono/tiolo)-fosforowych(fosfonowych) |
| BE180226A BE857855A (fr) | 1976-08-17 | 1977-08-17 | Nouveaux esters et amides d'esters d'isoxazolyle d'acide (thiono) (thiol)-phosphorique (phosphonique), leur procede de preparation et application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762637007 DE2637007A1 (de) | 1976-08-17 | 1976-08-17 | Isoxazolyl(thiono) (thiol)-phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2637007A1 true DE2637007A1 (de) | 1978-02-23 |
Family
ID=5985652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762637007 Pending DE2637007A1 (de) | 1976-08-17 | 1976-08-17 | Isoxazolyl(thiono) (thiol)-phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5323968A (pl) |
| BE (1) | BE857855A (pl) |
| BR (1) | BR7705411A (pl) |
| DE (1) | DE2637007A1 (pl) |
| DK (1) | DK364377A (pl) |
| ES (1) | ES461622A1 (pl) |
| FR (1) | FR2362153A1 (pl) |
| IL (1) | IL52735A0 (pl) |
| NL (1) | NL7709038A (pl) |
| PL (1) | PL200299A1 (pl) |
| PT (1) | PT66913B (pl) |
| SE (1) | SE7709226L (pl) |
| ZA (1) | ZA774940B (pl) |
-
1976
- 1976-08-17 DE DE19762637007 patent/DE2637007A1/de active Pending
-
1977
- 1977-08-12 PT PT66913A patent/PT66913B/pt unknown
- 1977-08-15 IL IL52735A patent/IL52735A0/xx unknown
- 1977-08-15 JP JP9709377A patent/JPS5323968A/ja active Pending
- 1977-08-16 FR FR7725045A patent/FR2362153A1/fr not_active Withdrawn
- 1977-08-16 ES ES461622A patent/ES461622A1/es not_active Expired
- 1977-08-16 BR BR7705411A patent/BR7705411A/pt unknown
- 1977-08-16 PL PL20029977A patent/PL200299A1/pl unknown
- 1977-08-16 NL NL7709038A patent/NL7709038A/xx not_active Application Discontinuation
- 1977-08-16 DK DK364377A patent/DK364377A/da unknown
- 1977-08-16 ZA ZA00774940A patent/ZA774940B/xx unknown
- 1977-08-16 SE SE7709226A patent/SE7709226L/xx unknown
- 1977-08-17 BE BE180226A patent/BE857855A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK364377A (da) | 1978-02-18 |
| ES461622A1 (es) | 1978-06-16 |
| BR7705411A (pt) | 1978-05-16 |
| IL52735A0 (en) | 1977-10-31 |
| PT66913B (de) | 1979-02-02 |
| FR2362153A1 (fr) | 1978-03-17 |
| BE857855A (fr) | 1978-02-17 |
| ZA774940B (en) | 1978-06-28 |
| JPS5323968A (en) | 1978-03-06 |
| PT66913A (de) | 1977-09-01 |
| PL200299A1 (pl) | 1978-04-10 |
| SE7709226L (sv) | 1978-02-18 |
| NL7709038A (nl) | 1978-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |