US3594400A - Cyanoalkyl-nitrophenyl carbonates - Google Patents
Cyanoalkyl-nitrophenyl carbonates Download PDFInfo
- Publication number
- US3594400A US3594400A US710630A US3594400DA US3594400A US 3594400 A US3594400 A US 3594400A US 710630 A US710630 A US 710630A US 3594400D A US3594400D A US 3594400DA US 3594400 A US3594400 A US 3594400A
- Authority
- US
- United States
- Prior art keywords
- compounds
- compound
- cyanoalkyl
- sec
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Definitions
- Nitrophenyl carbonates devoid of cyano substituents are known and have pesticidal activity.
- 3,287,611 discloses compounds of structure where R is lower alkyl and these compounds have acaricidal activity.
- US. 3,234,260 discloses similar acaricidal compounds which are further substituted in the phenyl ring.
- U .8. 3,198,824 discloses as fungicides and herbicides compounds of structure where R is alkyl and Ar is aryl.
- the compounds of the invention can be prepared by phosgenation of. the compound NC -R --0H giving NC-R O'CO--Cl and then reacting this compound with a dinitro-alkylphenol.
- the same type of compounds can be obtained by reaction of the appropriate chloroformic acid with the appropriate phenolate.
- the wettable powders contain 50-90 weight percent of the active compound and for the rest a dispersing agent, a wetting agent, and a carrier. If the active compound is a liquid or oil, the content of active compound is below 50 weight percent. The liquid compounds are then adsorbed on adsorbing carriers.
- Emulsifiable solutions can be obtained by the solution of the active compound in a solvent or mixture of solvents. Suitable solvents are alcohols, ketones, ethers, aromatic hydrocarbons and petroleum fractions.- As indicated, dispersing agents, wetting agents, or emulr sifying agents can be added. 0
- the compounds of the invention appear to be partic- Cl ularly suitable for a combined acaricidal and fungicidal -0-CH5 action and preferred species of useful compounds are (3H3 those identified above as C and F It will be understood that numerous changes and variajggz 83% tions may be made without departing from the spirit and s 1 OH CH 1 2O scope of the invention. ec.amy za E, d0 -oH1-oH2oN 0.80 We Glam- 1. A compound of structure F Sec.amyl H 5.00
- R is an alkyl group of one to ten carbon atoms H3 and R is a cyanoalkyl group containing from one to four carbon atoms in the alkyl group.
- Example H 2 A compound as in claim 1 where R is a secondary TABLE II Percent of glierkin surface covered with mildew after treatment Compound 80 p.p.m. 40 p.p.m. 20 p.p.m. 10 p.p.m.
- Example III The examination of the acaricidal action was carried out on mites of the genus -Bryodia on leaves of the brown bean. Leaves were sprayed in petri dishes with aqueous formulations of the active compounds in concentrations of 200, 40, and 8 p.p.m. in a quantity corresponding to 1,000 liters per hectare. Before the leaves were sprayed 25 living mites were present on each leaf. Tests were carried out in quadruple.; after 1 and 2 days the dead mites were counted.
- R is a secondary amyl group and R is CI-I CH CN.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL6703598A NL6703598A (ja) | 1967-03-07 | 1967-03-07 | |
US71063068A | 1968-03-05 | 1968-03-05 | |
US12852571A | 1971-03-26 | 1971-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3594400A true US3594400A (en) | 1971-07-20 |
Family
ID=27351399
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US710630A Expired - Lifetime US3594400A (en) | 1967-03-07 | 1968-03-05 | Cyanoalkyl-nitrophenyl carbonates |
US00128525A Expired - Lifetime US3723625A (en) | 1967-03-07 | 1971-03-26 | Process for killing plant pests using cyanoalkyl-nitrophenyl carbonates |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00128525A Expired - Lifetime US3723625A (en) | 1967-03-07 | 1971-03-26 | Process for killing plant pests using cyanoalkyl-nitrophenyl carbonates |
Country Status (5)
Country | Link |
---|---|
US (2) | US3594400A (ja) |
BE (1) | BE711353A (ja) |
FR (1) | FR1562303A (ja) |
GB (1) | GB1181596A (ja) |
NL (1) | NL6703598A (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4389411A (en) * | 1982-03-03 | 1983-06-21 | The Dow Chemical Company | Cyano-(2,4-dichlorophenyl)methyl ethyl ester of carbonic acid useful as a nematocide |
US4391630A (en) * | 1982-03-03 | 1983-07-05 | The Dow Chemical Company | Cyano-(4-cyanophenyl)methyl ethyl ester of carbonic acid useful as an agent for selective control of barnyard grass |
US4414218A (en) * | 1982-03-03 | 1983-11-08 | The Dow Chemical Company | Cyano-(substituted and unsubstituted pyridinyl) methyl and aryl esters of carbonic acid |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1070755A (en) * | 1964-08-07 | 1967-06-01 | Murphy Chemical Ltd | Improvements in or relating to 2,6-dinitro-4-alkylphenols and carbonates thereof |
US3287211A (en) * | 1965-02-26 | 1966-11-22 | Stauffer Chemical Co | Controlling mites with certain alkyl-(2, 4-dinitrophenyl) carbonates |
-
1967
- 1967-03-07 NL NL6703598A patent/NL6703598A/xx unknown
-
1968
- 1968-02-27 BE BE711353D patent/BE711353A/xx unknown
- 1968-03-05 US US710630A patent/US3594400A/en not_active Expired - Lifetime
- 1968-03-06 FR FR1562303D patent/FR1562303A/fr not_active Expired
- 1968-03-07 GB GB01117/68A patent/GB1181596A/en not_active Expired
-
1971
- 1971-03-26 US US00128525A patent/US3723625A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4389411A (en) * | 1982-03-03 | 1983-06-21 | The Dow Chemical Company | Cyano-(2,4-dichlorophenyl)methyl ethyl ester of carbonic acid useful as a nematocide |
US4391630A (en) * | 1982-03-03 | 1983-07-05 | The Dow Chemical Company | Cyano-(4-cyanophenyl)methyl ethyl ester of carbonic acid useful as an agent for selective control of barnyard grass |
US4414218A (en) * | 1982-03-03 | 1983-11-08 | The Dow Chemical Company | Cyano-(substituted and unsubstituted pyridinyl) methyl and aryl esters of carbonic acid |
Also Published As
Publication number | Publication date |
---|---|
FR1562303A (ja) | 1969-04-04 |
NL6703598A (ja) | 1968-09-09 |
GB1181596A (en) | 1970-02-18 |
US3723625A (en) | 1973-03-27 |
BE711353A (ja) | 1968-08-27 |
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