GB814198A - New thiophosphoric acid esters and their use in the control of pests - Google Patents
New thiophosphoric acid esters and their use in the control of pestsInfo
- Publication number
- GB814198A GB814198A GB19734/55A GB1973455A GB814198A GB 814198 A GB814198 A GB 814198A GB 19734/55 A GB19734/55 A GB 19734/55A GB 1973455 A GB1973455 A GB 1973455A GB 814198 A GB814198 A GB 814198A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- sulphur
- thiophosphate
- benzyl
- general 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.)
- Expired
Links
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title abstract 2
- 241000607479 Yersinia pestis Species 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 8
- 239000005864 Sulphur Substances 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- IBGCXOFOCKCBNQ-UHFFFAOYSA-N nitro cyanate Chemical compound [O-][N+](=O)OC#N IBGCXOFOCKCBNQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- -1 tetrahydrofurfuryl Chemical group 0.000 abstract 2
- DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 abstract 2
- PTGKQMHGAXCGMY-UHFFFAOYSA-N (2-ethylsulfanyl-5-phenylpentoxy)-dihydroxy-sulfanylidene-lambda5-phosphane Chemical compound CCSC(CCCC1=CC=CC=C1)COP(=S)(O)O PTGKQMHGAXCGMY-UHFFFAOYSA-N 0.000 abstract 1
- SXQOPTDMZVOKIQ-UHFFFAOYSA-N (4-cyclohexyl-2-ethylsulfanylbutoxy)-dihydroxy-sulfanylidene-lambda5-phosphane Chemical compound CCSC(CCC1CCCCC1)COP(=S)(O)O SXQOPTDMZVOKIQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N Diethyl sulfide Natural products CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 abstract 1
- JNKHXCUJVWCSFO-UHFFFAOYSA-N P(=S)(O)(O)O.C(C1=CC=CC=C1)CC[K] Chemical compound P(=S)(O)(O)O.C(C1=CC=CC=C1)CC[K] JNKHXCUJVWCSFO-UHFFFAOYSA-N 0.000 abstract 1
- CMRLUMXWVGYAKM-UHFFFAOYSA-N P(=S)(O)(O)O.C1(CCCCC1)CC[K] Chemical compound P(=S)(O)(O)O.C1(CCCCC1)CC[K] CMRLUMXWVGYAKM-UHFFFAOYSA-N 0.000 abstract 1
- PIYDIGIMGVHTNX-UHFFFAOYSA-N [2-cyclohexylethyl(2-ethylsulfanylethyl)-lambda4-sulfanylidene]-trihydroxy-lambda5-phosphane Chemical compound CCSCCS(=P(O)(O)O)CCC1CCCCC1 PIYDIGIMGVHTNX-UHFFFAOYSA-N 0.000 abstract 1
- DDMBTDCTYOAHBA-UHFFFAOYSA-N [2-ethylsulfanylethyl(3-phenylpropyl)-lambda4-sulfanylidene]-trihydroxy-lambda5-phosphane Chemical compound CCSCCS(=P(O)(O)O)CCCC1=CC=CC=C1 DDMBTDCTYOAHBA-UHFFFAOYSA-N 0.000 abstract 1
- KROGSUWKWSSROX-UHFFFAOYSA-N [2-ethylsulfanylethyl-[3-(oxolan-2-yl)propyl]-lambda4-sulfanylidene]-trihydroxy-lambda5-phosphane Chemical compound CCSCCS(=P(O)(O)O)CCCC1CCCO1 KROGSUWKWSSROX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 1
- FJPUYNBWPYLGKK-UHFFFAOYSA-N dihydroxy-[3-(oxolan-2-yl)propoxy]-sulfanylidene-lambda5-phosphane Chemical compound C(C1CCCO1)CCOP(O)(O)=S FJPUYNBWPYLGKK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- BBNYLDSWVXSNOQ-UHFFFAOYSA-N oxolane-2-carbaldehyde Chemical compound O=CC1CCCO1 BBNYLDSWVXSNOQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000005323 thioketone group Chemical group 0.000 abstract 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- 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
-
- 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
-
- 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
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
-
- 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
-
- 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
- C07F9/201—Esters of thiophosphorus acids
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (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)
Abstract
The invention comprises compounds of the general formula <FORM:0814198/IV (b)/1> in which one Z represents sulphur and the remaining Z's represent oxygen, R represents an alkyl radical containing not more than 4 carbon atoms and R1 represents a cycloaliphatic e.g. cyclohexyl, or araliphatic radical e.g. benzyl, or a radical of a heterocyclic compound free from enolisable ketone or thio ketone groups, e.g. tetrahydrofurfuryl, R2 represents an aliphatic radical which may be substituted with halogen thiocyanogen cyano, nitro ether or ester group and "alkeylene" represents an alkylene radical containing not more than 4 carbon atoms. They may be prepared by reacting a compound of the general formula <FORM:0814198/IV (b)/2> with a compound of the general formula Hal-alkylene-S-R2, or a compound of the general formula <FORM:0814198/IV (b)/3> with one of the general formula R1-Hal. R, R1, R2 and "alkylene" having the meanings given above and Me representing a metal atom, or by the additive combination of sulphur with a derivative of phosphorous acid of the general formula <FORM:0814198/IV (b)/4> Examples are given of the preparation of (1) tetra - hydro - furfuryl - ethyl - (ethylthioethyl) thiophosphate by treating the potassium salt of tetrahydrofurfurylethyl - thiophosphoric acid <FORM:0814198/IV (b)/5> with b - chloro - diethyl sulfide; (2) benzyl-ethyl - (ethylthio - ethyl) thiophosphate from benzyl-ethyl-potassium thiophosphate and b -chloro - ethyl - ethyl sulphide or by transesterifying diethyl phosphite with b -hydroxydiethyl-sulphide and converting with sulphur and K2CO3 and treating the product with benzyl chloride; (3) cyclohexyl-ethyl-(ethyl thio ethyl) thiophosphate from b -chloro diethyl sulphide and cyclohexyl ethyl-potassium thiophosphate; (4) the addition product of sulphur and benzyl ethyl-(b -ethyl-thioethyl) phosphite; (5) the addition product of sulphur and parachlorobenzyl-ethyl-(ethyl-thioethyl) phosphite.ALSO:Pesticidal preparations comprise as active ingredients thiophosphoric acid esters of the general formula <FORM:0814198/VI/1> in which one Z represents sulphur and the remaining Z's represent oxygen, R represents an alkyl radical containing not more than 4 C atoms, R1 represents a cycloaliphatic, e.g. cyclohexyl, araliphatic, e.g. benzyl, or heterocyclic radical free from enolizable ketone or thioketane groups, e.g. tetrahydrofurfural, R2 represents an aliphatic radical which may be substituted with halogen, thiocyanogen, cyano nitro ether or ester groups, and "alkylene" represents an alkylene radical containing not more than 4 C atoms and a solid or liquid diluent or solvent. Other insecticides and/or fungicides may be incorporated in the composition. Specified compounds are tetrahydrofurfurylethyl - (ethyl - thioethyl) - thiophosphate, benzyl - ethyl - (ethylthio - ethyl) - thiophosphate, cyclohexyl - ethyl - (ethyl - thioethyl) - thiophosphate, the addition product of sulphur and para - chlorobenzyl - ethyl - (ethyl - thioethyl) - thio phosphite, and the addition product of sulphur and benzyl ethyl-(b -ethyl-thioethyl)-phosphite.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH814198X | 1954-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814198A true GB814198A (en) | 1959-06-03 |
Family
ID=4538793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19734/55A Expired GB814198A (en) | 1954-09-29 | 1955-07-07 | New thiophosphoric acid esters and their use in the control of pests |
Country Status (4)
| Country | Link |
|---|---|
| BE (2) | BE539661A (en) |
| DE (1) | DE1012112B (en) |
| FR (2) | FR1164211A (en) |
| GB (1) | GB814198A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL288076A (en) * | 1962-01-24 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2571989A (en) * | 1949-09-28 | 1951-10-16 | Bayer Ag | Neutral esters of thiophosphoric acid |
-
0
- BE BE539662D patent/BE539662A/xx unknown
- BE BE539661D patent/BE539661A/xx unknown
-
1955
- 1955-06-27 DE DEC11457A patent/DE1012112B/en active Pending
- 1955-07-05 FR FR1164211D patent/FR1164211A/en not_active Expired
- 1955-07-05 FR FR1164210D patent/FR1164210A/en not_active Expired
- 1955-07-07 GB GB19734/55A patent/GB814198A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1164211A (en) | 1958-10-07 |
| BE539662A (en) | |
| FR1164210A (en) | 1958-10-07 |
| BE539661A (en) | |
| DE1012112B (en) | 1957-07-11 |
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