US3594400A - Cyanoalkyl-nitrophenyl carbonates - Google Patents

Cyanoalkyl-nitrophenyl carbonates Download PDF

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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
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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
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US710630A
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English (en)
Inventor
Krijn Van Den Boogaart
Meelis Nicolaus Louis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nv Fabriek Van Chemische Producten Vondelingenplaat
VONDELINGEN PLAAT BV
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VONDELINGEN PLAAT BV
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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US710630A 1967-03-07 1968-03-05 Cyanoalkyl-nitrophenyl carbonates Expired - Lifetime US3594400A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NL6703598A NL6703598A (de) 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 (de)
BE (1) BE711353A (de)
FR (1) FR1562303A (de)
GB (1) GB1181596A (de)
NL (1) NL6703598A (de)

Cited By (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (3)

* Cited by examiner, † Cited by third party
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
BE711353A (de) 1968-08-27
GB1181596A (en) 1970-02-18
NL6703598A (de) 1968-09-09
FR1562303A (de) 1969-04-04
US3723625A (en) 1973-03-27

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