Claims
- 1. A compound of the formula ##STR14## wherein W and X are each hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;
- Y is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;
- Z is fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms, chloro-substituted alkyl of 1 to 4 carbon atoms, --COOH or --COO--(alkyl of 1 to 4 carbon atoms); and
- n is 1;
- or, when Z is --COOH, an alkali or alkaline earth metal salt thereof.
- 2. A compound of claim 1,
- where
- W and X are each hydrogen, fluorine, chlorine, methyl, trifluoromethyl or nitro;
- Y is hydrogen, fluorine, chlorine, methyl, trifluoromethyl or trichloromethyl;
- Z is fluorine, chlorine, methyl, trifluoromethyl or carboxyl; and
- n is 1;
- or, when Z is carboxyl, an alkali or alkaline earth metal salt thereof.
- 3. A compound of claim 1, where said salt is an alkali metal salt.
- 4. A compound of claim 2, where said salt is an alkali metal salt.
- 5. An herbicidal composition consisting essentially of an effective herbicidal amount of a compound of claim 1 in combination with an inert carrier.
- 6. The method of killing weeds, which comprises contacting said weeds with an effective herbicidal amount of a composition of claim 5.
- 7. The method of killing weeds, which comprises contacting said weeds with an effective herbicidal amount of a compound of claim 1.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 3205150 |
Feb 1982 |
DEX |
|
THE PRIOR ART
This is a continuation of copending application Ser. No. 462,150, filed Jan. 31, 193, now abandoned.
This invention relates to novel 4-phenoxy-substituted pyridines, to a method of preparing these compounds, to herbicidal compositions containing them as active ingredients, and to a method of using them as selective herbicides.
German Offenlegungsschrift No. 1,542,736 discloses herbicidal aryloxy-substituted pyridines of the formula ##STR2## and particularly the compound of the formula ##STR3## However, these compounds, which lack additional substituents on the pyridine ring, do not exhibit satisfactory herbicidal properties.
It is an object of the present invention to provide novel phenoxy-substituted pyridines having one or more additional substituents attached to the pyridine ring, which are more effective herbicides than the prior art compounds.
Other objects and advantages of the invention will become apparent as the description thereof proceeds.
More particularly, the present invention relates to a novel class of compounds represented by the formula ##STR4## wherein W and X, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 4 carbon atoms;
Those alkyl radicals in formula I which contain 3 or 4 carbon atoms may be straight-chain or branched-chain alkyls. Preferred fluoro-alkyls and chloro-alkyls are trifluoromethyl or trichloromethyl.
Preferred embodiments of variables W, X, Y, Z and n are the following
The compounds embraced by formula I may be prepared by a method involving known chemical synthesis principles, namely by reacting a pyridine derivative of the formula ##STR5## wherein Y and X have the same meanings as in formula I, and A is halogen, especially chlorine or fluorine, or nitro,
The reaction is carried out at temperatures between ambient temperature and about 160.degree. C., preferably in a polar solvent, such as acetone, butan-2-one, acetonitrile, dimethylformamide or dimethylsulfoxide, at room temperature or moderately elevated temperature. If the reaction is performed with a phenol of the formula IIIa, an acid-binding agent, for example an alkali metal carbonate, such as sodium carbonate or potassium carbonate, or an alkali metal or alkaline earth metal hydroxide such as sodium hydroxide, potassium hydroxide or calcium hydroxide, is added to the reaction mixture. In order to achieve a favorable yield, it can be of advantage to provide the phenol or phenolate and/or the acid-binding agent in excess.
The starting compounds of the formulas II, IIIa and IIIb are either known compounds or may be prepared by the same method as the known compounds.
US Referenced Citations (5)
| Number |
Name |
Date |
Kind |
| 3429689 |
Duerr et al. |
Feb 1969 |
|
| 4076741 |
Bayer et al. |
Feb 1978 |
|
| 4235621 |
Nishiyama et al. |
Nov 1980 |
|
| 4317913 |
Cartwright |
Mar 1982 |
|
| 4453972 |
Schroder et al. |
Jun 1984 |
|
Continuations (1)
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Number |
Date |
Country |
| Parent |
462150 |
Jan 1983 |
|
Patent Grant
4655824
