GB833156A - O-aryl phosphoroamidohydrazidothioates - Google Patents
O-aryl phosphoroamidohydrazidothioatesInfo
- Publication number
- GB833156A GB833156A GB1326758A GB1326758A GB833156A GB 833156 A GB833156 A GB 833156A GB 1326758 A GB1326758 A GB 1326758A GB 1326758 A GB1326758 A GB 1326758A GB 833156 A GB833156 A GB 833156A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aryl
- alkyl
- phenyl
- trichlorophenyl
- cyclohexyl
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 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 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- -1 2,4,5 - trichlorophenyl Chemical group 0.000 abstract 1
- RAYLGGLDHQNXPR-UHFFFAOYSA-N O-[amino(methylamino)phosphinothioyl]hydroxylamine Chemical compound P(NC)(N)(ON)=S RAYLGGLDHQNXPR-UHFFFAOYSA-N 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- KXMQPGJXTIKBSV-UHFFFAOYSA-N ctk0i0198 Chemical compound NP(O)(Cl)=S KXMQPGJXTIKBSV-UHFFFAOYSA-N 0.000 abstract 1
- OOFVSLAKBNBEEH-UHFFFAOYSA-N dichloro-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(Cl)(Cl)=S OOFVSLAKBNBEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 1
- 229940067157 phenylhydrazine Drugs 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000007858 starting material 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2491—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-N (X = O, S, Se; n = 0, 1)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (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
The invention comprises O-aryl phosphoroamidohydrazidothioates having the formula <FORM:0833156/IV (b)/1> in which X is aryl, as defined below, R1 and R4 are hydrogen or C1-C4 alkyl, R2 is C1-C4 alkyl or cyclohexyl, and R3 is hydrogen, C1-C4 alkyl, or phenyl. The term aryl is defined as a phenyl radical or a substituted phenyl radical containing one or more substituents including chlorine, bromine, C1-C4 alkyl, cyclohexyl, phenyl, benzyl, C1-C4 alkoxy group or nitro group. They may be obtained by reacting hydrazine, or an appropriately substituted hydrazine, e.g. phenylhydrazine or a C1-C4 alkylhydrazine with a phosphoroamidochloridothioate of the formula <FORM:0833156/IV (b)/2> in the presence of an inert organic solvent, e.g. benzene, toluene or methyl chloride. Suitable reaction temperatures are from 0 DEG to 50 DEG C. Upon completion of the reaction the reaction mixture is washed with water and any reaction solvent removed by evaporation or partial distillation under reduced pressure to obtain the desired product as a residue. Examples are given for the production O-(2,4,5-trichlorophenyl) N-methyl phosphoroamidohydrazidothioate, O-(2,4,5-trichlorophenyl) -N-methyl-2-phenylphosphoramidohydrazidothioate, O-(2,4, 5-trichlorophenyl - N,2,2 - trimethylphosphoroamidohydrazidothioate, and O - (4 - chloro - 2 - cyclohexylphenyl) - N - cyclohexylphosphoroamidohydrazidothioate. The products have good pesticidal properties (see Group VI). The O-aryl phosphoroamidochloridothioates used as starting materials may be obtained by reacting two molecular proportions of an appropriately substituted amine, e.g. a C1-C4 alkylamine or cyclohexylamine with one molecular proportion of an O-aryl phosphorodichloridothioate at from -10 DEG to 50 DEG C., the reaction being carried out by adding a benzene solution of the amine portionwise to the phosphorodichloridothioate dissolved in benzene.ALSO:O-Aryl phosphoroamidohydrazidothioates of the general formula <FORM:0833156/VI/1> in which X is aryl as defined below, R1 and R4 are hydrogen or C1-C4 alkyl, R2 is C1-C4 alkyl or cyclohexyl and R3 is hydrogen, C1-C4 alkyl or phenyl (see Group IV (b)), the term aryl being defined as a phenyl radical or a substituted phenyl radical containing one or more substituents including chlorine, bromine, C1-C4 alkyl, cyclohexyl, phenyl, benzyl, C1-C4 alkoxy group or nitro group, are effective as fungicides and parasilicides. They may be dispersed on a finely divided carrier and employed as dusts or they may be used in oils or as constituents in water emulsions or water dispersions. A suitable insecticidal composition comprises an aqueous composition containing two pounds of O - (2,4,5 - trichlorophenyl) - N - methyl - 2 - phenylphosphoroamidohydrazidothioate per 100 gallons of water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1326758A GB833156A (en) | 1958-04-25 | 1958-04-25 | O-aryl phosphoroamidohydrazidothioates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1326758A GB833156A (en) | 1958-04-25 | 1958-04-25 | O-aryl phosphoroamidohydrazidothioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB833156A true GB833156A (en) | 1960-04-21 |
Family
ID=10019871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1326758A Expired GB833156A (en) | 1958-04-25 | 1958-04-25 | O-aryl phosphoroamidohydrazidothioates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB833156A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997002275A1 (en) * | 1995-07-05 | 1997-01-23 | Uniroyal Chemical Company, Inc. | Pesticidal phenylhydrazine phosphorus derivatives |
-
1958
- 1958-04-25 GB GB1326758A patent/GB833156A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997002275A1 (en) * | 1995-07-05 | 1997-01-23 | Uniroyal Chemical Company, Inc. | Pesticidal phenylhydrazine phosphorus derivatives |
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