GB1087029A - Phosphorothiolthionic esters - Google Patents
Phosphorothiolthionic estersInfo
- Publication number
- GB1087029A GB1087029A GB29604/66A GB2960466A GB1087029A GB 1087029 A GB1087029 A GB 1087029A GB 29604/66 A GB29604/66 A GB 29604/66A GB 2960466 A GB2960466 A GB 2960466A GB 1087029 A GB1087029 A GB 1087029A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen
- aralkyl
- dimethylamino
- aryl
- bis
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- LAQLKHRCYBCWJS-UHFFFAOYSA-N 2,6-bis(dimethylamino)-1h-1,3,5-triazin-4-one Chemical compound CN(C)C1=NC(=O)N=C(N(C)C)N1 LAQLKHRCYBCWJS-UHFFFAOYSA-N 0.000 abstract 1
- IHNFSEWKQNJQSJ-UHFFFAOYSA-N 6-iodo-2-n,2-n,4-n,4-n-tetramethyl-1,3,5-triazine-2,4-diamine Chemical compound CN(C)C1=NC(I)=NC(N(C)C)=N1 IHNFSEWKQNJQSJ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000010426 asphalt Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 239000000084 colloidal system Substances 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- 235000019830 sodium polyphosphate Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 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
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Novel compounds of the formula <FORM:1087029/C2/1> where R1 and R2 are the same or different and each represents halogen or an amino group in which one or both H atoms are replaced by alkyl, aralkyl or aryl, any of which may be substituted provided that only one of R1 and R2 may be halogen, and each of R3 and R4 represents alkoxy are prepared by reacting an ammonium or an alkali metal salt of a dialkyl-dithiophosphoric acid with at least an equimolar amount of 2,4,6-trichloro-1,3,5-triazine in the presence of an inert solvent and reacting the resulting dichlorotriazinyl phosphorothiol-thionic acid dialkyl ester with an aliphatic or aromatic amine. Both stages of the reaction are preferably carried out below 20 DEG C. The aryl, aralkyl and alkyl substituents on the amino groups may be substituted, e.g. by halogen. The compounds are bicides. The compounds undergo reactions with anions, e.g. iodide and hydroxide ions, thus when 2,4-bis-(dimethylamino) - 5 - triazin - 6 - yl phosphoro-thiolthionic acid dimethyl ester is treated with NaI or subjected to alkaline hydrolysis the products are 2,4-bis-(dimethylamino)-6-iodo-s-triazine and 2,4-bis-(dimethylamino)-6-hydroxyl-s-triazine respectively. Specification 993,813 is referred to.ALSO:Biocidal, (including pesticidal and herbicidal) compositions contain, as active ingredient, a compound of formula: <FORM:1087029/A5-A6/1> where R1 and R2 are the same or different and each represents halogen or an amino group in which one or both hydrogen atoms are replaced by alkyl, aralkyl or aryl, any of which may be substituted provided that only one of R1 and R2 may be halogen, and R3 and R4 represent alkoxy, together with a carrier or a surface active agent or both. Suitable carriers are silicates, clays, elements, e.g. C and S, natural and synthetic resins, bitumen, ashphaltite, waxes, fertilisers, water, alcohols, ketones, ethers, hydro-carbons, and petroleum fractions. The surface active agent may be an ionic or a nonionic wetting, emulsifying or dispersing agent. The compositions may be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates and emulsions, and may contain other ingredients, e.g. protective colloids, polyvinyl alcohol sodium polyphosphates, cellulose ethers, stabilisers, other unspecified herbicides or pesticides, and stickers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29604/66A GB1087029A (en) | 1966-07-01 | 1966-07-01 | Phosphorothiolthionic esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29604/66A GB1087029A (en) | 1966-07-01 | 1966-07-01 | Phosphorothiolthionic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1087029A true GB1087029A (en) | 1967-10-11 |
Family
ID=10294177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29604/66A Expired GB1087029A (en) | 1966-07-01 | 1966-07-01 | Phosphorothiolthionic esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1087029A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935516A1 (en) * | 1978-09-04 | 1980-03-20 | Sumitomo Chemical Co | ORGANOPHOSPHORESTER, METHOD FOR THE PRODUCTION THEREOF, PESTICIDES CONTAINING THESE COMPOUNDS AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATOCIDS |
-
1966
- 1966-07-01 GB GB29604/66A patent/GB1087029A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935516A1 (en) * | 1978-09-04 | 1980-03-20 | Sumitomo Chemical Co | ORGANOPHOSPHORESTER, METHOD FOR THE PRODUCTION THEREOF, PESTICIDES CONTAINING THESE COMPOUNDS AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATOCIDS |
| FR2434817A1 (en) * | 1978-09-04 | 1980-03-28 | Sumitomo Chemical Co | ORGANOPHOSPHORUS ESTERS, THEIR PREPARATION AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATOCIDES |
| US4320126A (en) | 1978-09-04 | 1982-03-16 | Sumitomo Chemical Company, Limited | Triazinyl-organophosphorus esters |
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