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
- 150000001875 compounds Chemical class 0.000 abstract description 38
- 239000000642 acaricide Substances 0.000 abstract description 4
- 230000000855 fungicidal effect Effects 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000895 acaricidal effect Effects 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JPNBVWIRDQVGAC-UHFFFAOYSA-N (2-nitrophenyl) hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1[N+]([O-])=O JPNBVWIRDQVGAC-UHFFFAOYSA-N 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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 (en, 2012) | 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 (en, 2012) |
| BE (1) | BE711353A (en, 2012) |
| FR (1) | FR1562303A (en, 2012) |
| GB (1) | GB1181596A (en, 2012) |
| NL (1) | NL6703598A (en, 2012) |
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 |
|---|---|---|---|---|
| GB1070756A (en) * | 1964-08-07 | 1967-06-01 | Murphy Chemical Ltd | Improvements in or relating to dinitrophenyl carbonates and their use as pesticides |
| 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 |
|---|---|
| GB1181596A (en) | 1970-02-18 |
| US3723625A (en) | 1973-03-27 |
| FR1562303A (en, 2012) | 1969-04-04 |
| BE711353A (en, 2012) | 1968-08-27 |
| NL6703598A (en, 2012) | 1968-09-09 |
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