GB589340A - Manufacture of condensation products, being more especially active vermin combating or insecticidal compounds, and formation of liquid and dry insecticides therewith - Google Patents
Manufacture of condensation products, being more especially active vermin combating or insecticidal compounds, and formation of liquid and dry insecticides therewithInfo
- Publication number
- GB589340A GB589340A GB4077/44A GB407744A GB589340A GB 589340 A GB589340 A GB 589340A GB 4077/44 A GB4077/44 A GB 4077/44A GB 407744 A GB407744 A GB 407744A GB 589340 A GB589340 A GB 589340A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitroethane
- phenyl
- tolyl
- chlorophenyl
- mixed
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 239000007859 condensation product Substances 0.000 title abstract 3
- 230000000749 insecticidal effect Effects 0.000 title abstract 3
- 239000002917 insecticide Substances 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000007788 liquid Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 15
- 239000000243 solution Substances 0.000 abstract 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 4
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- XUEWIQNQPBSCOR-UHFFFAOYSA-N 2-nitro-1-phenylethanol Chemical class [O-][N+](=O)CC(O)C1=CC=CC=C1 XUEWIQNQPBSCOR-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 239000000440 bentonite Substances 0.000 abstract 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 3
- 239000005018 casein Substances 0.000 abstract 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 abstract 3
- 235000021240 caseins Nutrition 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 239000000080 wetting agent Substances 0.000 abstract 3
- DLRZMMQNDITSLC-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)-2-nitroethyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(C[N+]([O-])=O)C1=CC=C(Cl)C=C1 DLRZMMQNDITSLC-UHFFFAOYSA-N 0.000 abstract 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 abstract 2
- LOBGEAACSVHURG-UHFFFAOYSA-N 1-methyl-4-(2-nitro-1-phenylethyl)benzene Chemical compound C1=CC(C)=CC=C1C(C[N+]([O-])=O)C1=CC=CC=C1 LOBGEAACSVHURG-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000001828 Gelatine Substances 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 2
- 229910000278 bentonite Inorganic materials 0.000 abstract 2
- 150000001555 benzenes Chemical class 0.000 abstract 2
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- -1 dimethyl phenyl Chemical group 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 229920000159 gelatin Polymers 0.000 abstract 2
- 235000019322 gelatine Nutrition 0.000 abstract 2
- 239000003292 glue Substances 0.000 abstract 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 2
- 235000010413 sodium alginate Nutrition 0.000 abstract 2
- 239000000661 sodium alginate Substances 0.000 abstract 2
- 229940005550 sodium alginate Drugs 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- XBOXUESMPMNDAK-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-nitroethanol Chemical compound ClC1=CC=C(C=C1)C(C)(O)[N+](=O)[O-] XBOXUESMPMNDAK-UHFFFAOYSA-N 0.000 abstract 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 1
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 abstract 1
- QKOIJHPIFXIYEK-UHFFFAOYSA-N 1-chloro-4-(2-nitro-1-phenylethyl)benzene Chemical compound C=1C=C(Cl)C=CC=1C(C[N+](=O)[O-])C1=CC=CC=C1 QKOIJHPIFXIYEK-UHFFFAOYSA-N 0.000 abstract 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910000281 calcium bentonite Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229940078552 o-xylene Drugs 0.000 abstract 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A condensation product having insecticidal properties is made by condensing a 1-phenyl or substituted phenyl - 2 - nitroethanol with an aromatic compound of the benzene series. The condensation is carried out in the presence of the usual condensation agents such as sulphuric acid, aluminium chloride and zinc chloride. The products are applied in the form of solutions or emulsions or mixed with inert diluents. In examples: (1) p-chlorobenzaldehyde and nitromethane are treated with sodium methylate in methyl alcohol to give p-chlorophenyl nitro ethanol which is then reacted with chlorobenzene in the presence of sulphuric acid to form 1 : 1-di-(p-chlorophenyl)-2-nitroethane. By starting with p-tolualdehyde, nitromethane and toluene there is obtained 1 : 1-di-(p-tolyl)-2-nitroethane, and using 3 : 4-dimethyl-benzaldehyde, nitromethene and o-xylene there is obtained 1 : 1-di-(31 : 41-dimethylphenyl)-2-nitroethane. (2) The 1-phenyl-2-nitroethanol obtained as in example (1) is condensed with chlorobenzene in the presence of sulphuric acid to give 1-phenyl-1-p-chlorophenyl-2-nitroethane. Other compounds mentioned which may be produced in an analogous manner are 1-p-tolyl-1-phenyl-2-nitroethane, 1-p-tolyl-1-p-chlorophenyl-2-nitroethane, 1-phenyl-1-(31 : 41-dimethylphenyl)2-nitroethane, 1-p-tolyl-1-(31 : 41-dimethylphenyl)-2-nitroethane, 1 : 1-diphenyl-2-nitroethane, 1 : 1-di-(p-bromophenyl)-2-nitroethane, and 1-(21 : 61-dichlorophenyl)-1-(411-chlorophenyl)2-nitroethane; (3) 1 : 1-di-(p-chlorophenyl)-2-nitroethane in chloroform is mixed with bole and evaporated; (4) 1 : 1-di-p-tolyl-2-nitroethane is mixed with magnesia usta and evaporated; (5) 1 : 1-diphenyl-2-nitroethane in ethyl acetate is mixed with bentonite, evaporated and powdered with gelatine and potassium chromate; (6) calcium carbonate and bentonite are saturated with an alcoholic solution of 1 : 1 - di - p - bromophenyl - 2 - nitroethane and the dried powder mixed with casein, sodium carbonate and a wetting agent such as dodecyl alcohol sulphonate; (7) a solution is prepared of 1 : 1 - di - p - tolyl - 2 - nitroethane methyl hexaline, toluene and soft soap; (8) methyl hexaline is added to a toluene solution of 1 - (21 : 61-dichlorophenyl) - 1 - (411-chlorophenyl) - 2-nitroethane and the product added to a quaternary wetting agent; (9) a toluene solution of 1 : 1-di-p-bromophenyl-2-nitroethane is added to methyl hexaline and the solution added to an aqueous solution of stearyl alcohol sulphonate to form an emulsion; (10) a toluene solution of 1 : 1-diphenyl-2-nitroethane and methyl hexaline is mixed with an aqueous solution of sodium alginate. If desired, glue, casein, or albuminous decomposition products may be used instead of sodium alginate.ALSO:Insecticides comprise a condensation product of a 1-phenyl or substituted phenyl-2-nitroethanol with an aromatic compound of the benzene series. Compounds mentioned are 1 : 1-di-(p-chlorophenyl)-2-nitroethane, 1 : 1-di-(p-tolyl)-2-nitroethane, 1 : 1-di-(31 : 41 dimethyl phenyl) - 2 - nitroethane, 1 - p - tolyl-1-phenyl-2-nitroethane, 1-p-tolyl-1-p-chlorophenyl-2-nitroethane, 1 - phenyl - 1 - (31-41-dimethylphenyl)-2-nitroethane, 1-p-tolyl-1-(31 : 41-dimethylphenyl)-2-nitroethane, 1 : 1-diphenyl-2-nitroethane, 1 : 1-di-(p-bromo-phenyl)-2-nitroethane, and 1-(21 : 61-dichlorophenyl)-1-(411-chlorophenyl)-2 - nitroethane. Additional ingredients of the insecticidal compositions which are mentioned include bole, bentonite, calcium carbonate, casein, glue, gelatine, albuminous decomposition products, methylhexaline, and wetting agents such as dodecyl alcohol sulphonate and stearyl alcohol sulphonate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH589340X | 1943-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB589340A true GB589340A (en) | 1947-06-18 |
Family
ID=4522039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4077/44A Expired GB589340A (en) | 1943-03-05 | 1944-03-04 | Manufacture of condensation products, being more especially active vermin combating or insecticidal compounds, and formation of liquid and dry insecticides therewith |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH236227A (en) |
| GB (1) | GB589340A (en) |
| NL (1) | NL64866C (en) |
-
0
- NL NL64866D patent/NL64866C/xx active
-
1943
- 1943-03-05 CH CH236227D patent/CH236227A/en unknown
-
1944
- 1944-03-04 GB GB4077/44A patent/GB589340A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL64866C (en) | |
| CH236227A (en) | 1945-01-31 |
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