GB1357154A - Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing them - Google Patents
Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing themInfo
- Publication number
- GB1357154A GB1357154A GB4444871A GB4444871A GB1357154A GB 1357154 A GB1357154 A GB 1357154A GB 4444871 A GB4444871 A GB 4444871A GB 4444871 A GB4444871 A GB 4444871A GB 1357154 A GB1357154 A GB 1357154A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dinitro
- dialkyl
- alkyl
- alkylthio
- carbon atoms
- 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
- 230000002363 herbicidal effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 5
- -1 3,5- dinitro - 4 - hydroxyphenyl Chemical group 0.000 abstract 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- XMXCZRKAAPXUTD-UHFFFAOYSA-N 4-methylsulfinyl-2,6-dinitro-N,N-dipropylaniline Chemical compound CS(=O)C1=CC(=C(N(CCC)CCC)C(=C1)[N+](=O)[O-])[N+](=O)[O-] XMXCZRKAAPXUTD-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910001508 alkali metal halide Inorganic materials 0.000 abstract 1
- 150000008045 alkali metal halides Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1357154 Nitroaniline derivatives SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 23 Sept 1971 [25 Sept 1970 (2)] 44448/71 Heading C2C Nitroaniline derivatives of a general formula in which R is lower alkyl of 1 to 3 carbon atoms , R<SP>1</SP> and R<SP>11</SP> are each the same or different and represent alkyl of 1 to 7 carbon atoms, alkenyl of 2 to 7 carbon atoms or cycloalkyl with 3 to 7 carbon atoms with the proviso that R<SP>1</SP> and R<SP>11</SP> combined do not contain more than 8 carbon atoms, and n is zero or one are prepared when n is 0 by (a) reacting a 4-(alkylthio)phenol with a dialkyl sulphate to form a 4-hydroxyphenyl dialkyl sulphonium alkyl sulphate; (b) dinitrating the resulting 4-hydroxyphenyl dialkyl sulphonium alkyl sulphate with nitric acid in the presence of sulphuric acid to form a (3,5- dinitro - 4 - hydroxyphenyl)dialkyl sulphonium alkyl sulphate; (c) reacting the (3,5-dinitro-4- hydroxyphenyl)dialkyl sulphonium alkyl sulphate with an aqueous alkali metal halide to form a 2,6 - dinitro - 4 - (alkylthio)phenol; (d) reacting 2,6 - 6 - dinitro - 4 - (alkylthio)- phenol with a chlorinating agent selected from the group consisting of thionyl chloride, phosgene or phosphorus oxychloride in carbon tetrachloride in the presence of a catalytic amount of dimethylformamide to form a 4 - chloro - 3,5 - dinitro - phenyl alkyl sulphide; and (e) treating the 4-chloro-3,5-dinitrophenyl alkyl sulphide with a dialkyl amine to form a 4 - (alkylthio) - 2,6 - dinitro - N,N - dialkylaniline; when n is 1 the compound formed in (e) above is oxidized to form 4-(alkylsulphinyl)- 2,6 - dinitro - N,N - dialkyl - aniline. There is also described the preparation of 4-(methylsulphonyl) - 2,6 - dinitro - N,N - dipropyl aniline by oxidizing the 4-(methylthio-2,6- dinitro - N,N dipropylaniline and the 4- (methylsulphinyl) - 2,6 - dinitro - N,N - dipropyl aniline with hydrogen peroxide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7568370A | 1970-09-25 | 1970-09-25 | |
| US7568470A | 1970-09-25 | 1970-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1357154A true GB1357154A (en) | 1974-06-19 |
Family
ID=26757153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4444871A Expired GB1357154A (en) | 1970-09-25 | 1971-09-23 | Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing them |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2147610A1 (en) |
| FR (1) | FR2112978A5 (en) |
| GB (1) | GB1357154A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0026307A1 (en) * | 1979-08-15 | 1981-04-08 | Merck & Co. Inc. | Organic sulfoxides, process for preparing the same and pharmaceutical enzyme inhibiting compositions comprising the same |
| US4388475A (en) | 1979-08-15 | 1983-06-14 | Merck & Co., Inc. | Allylsulfoxide enzyme inhibitors |
| US4558071A (en) * | 1979-08-15 | 1985-12-10 | Merck & Co., Inc. | Phenyl, trihalomethyl or heteroaryl sulfoxides having a latent allyl group bound to sulfur as enzyme inhibitors |
-
1971
- 1971-09-23 DE DE19712147610 patent/DE2147610A1/en active Pending
- 1971-09-23 FR FR7134233A patent/FR2112978A5/fr not_active Expired
- 1971-09-23 GB GB4444871A patent/GB1357154A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0026307A1 (en) * | 1979-08-15 | 1981-04-08 | Merck & Co. Inc. | Organic sulfoxides, process for preparing the same and pharmaceutical enzyme inhibiting compositions comprising the same |
| US4388475A (en) | 1979-08-15 | 1983-06-14 | Merck & Co., Inc. | Allylsulfoxide enzyme inhibitors |
| US4558071A (en) * | 1979-08-15 | 1985-12-10 | Merck & Co., Inc. | Phenyl, trihalomethyl or heteroaryl sulfoxides having a latent allyl group bound to sulfur as enzyme inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2112978A5 (en) | 1972-06-23 |
| DE2147610A1 (en) | 1972-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |