The Dow Chemical Company

Lillian H Troxell

Howard Johnston

Robert J Ehr

Helen K Tobol

Jon S Claus

Certain novel pyridinyloxyphenoxy alkanoic acids, pyridinylthiophenoxy alkanoic acids, derivatives thereof and related compounds are described. More specifically, these novel compounds bear a fluorine substituent in the 3-position of the pyridinyl group and in the 5-position the substituent is selected from chlorine, CF.sub.3, CF.sub.2 Cl or CF.sub.2 H. These novel compounds exhibit surprising preemergent and postemergent activity in the control of grassy weeds.

2,3-Difluoropyridine and 3-fluoro-2-pyridinyloxyphenol compounds

Compounds according to the following formula are useful as herbicidal agents: ##STR1## wherein the various substituents are defined hereinbelow.

Trifluoromethyl pyridinyloxyphenoxy and pyridinylthiophenoxy propanoic

Certain pyridyloxy or thio-phenoxy-propanoic acids or salts thereof

6-Halo(or CF.sub.3)-4-((di- or tri)halomethyl)-2-pyridinyl esters of carboxylic, carbonic, carbamic, thiocarbamic, sulfonic, or sulfamic acids, exemplified by 6-chloro-4-(trichloromethyl)-2-pyridinyl pentanoate, 4-methylbenzenesulfonate or methylcarbamate, are novel and are useful in the protection of plants from attack by soil-borne fungi.

Fungicidal control employing ester derivatives of 4,6-disubstituted

Novel compounds used as intermediates for making herbicides are disclosed. The novel compounds include acid chlorides of 2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid and 2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propionic acid.

Trifluoromethyl pyridinyloxyphenoxy propanoic acid chlorides

Pyridyl(oxy/thio)phenoxy compounds, herbicidal compositions and methods

2-((4-pyridinyl-2-oxy)phenoxy)propanoic acids, amides, salts and esters thereof, and nitriles derived therefrom and 2-((4-pyridinyl-2-oxy)phenoxy) propanols and esters and ethers thereof, and the corresponding 2-((4-pyridinyl-2-thio)phenoxy) propanoate and propanol compounds, all having trifluoromethyl substitution in at least one of the 3- and the 5-position in the pyridine ring with or without additional substitution at the converse position in the pyridine ring according to the following formula, are useful as herbicidal agents: ##STR1## wherein the various substituents are defined hereinbelow.

Herbicidal trifluoromethyl pyridinyloxyphenoxy and pyridinylthiophenoxy

2-((4-Pyridinyl-2-oxy)phenoxy)propanoic acids, amides, salts and esters thereof, and nitriles derived therefrom and 2-((4-pyridinyl-2-oxy)phenoxy) propanols and esters and ethers thereof, and the corresponding 2-((4-pyridinyl-2-thio)phenoxy) propanoate and propanol compounds, all having trifluoromethyl substitution in at least one of the 3- and the 5-position in the pyridine ring with or without additional substitution at the converse position in the pyridine ring according to the following formula, are useful as herbicidal agents: ##STR1## wherein the various substituents are defined hereinbelow.

Preparation of trifluoromethyl pyridinyloxyphenoxy propanoic acids and

2-((4-Pyridinyl-2-oxy)phenoxy)propanoic acids, amides, salts and esters thereof, and nitriles derived therefrom and 2-((4-pyridinyl-2-oxy)phenoxy) propanols and esters and ethers thereof, and the corresponding 2-((4-pyridinyl-2-thio)phenoxy) propanoate and propanol compounds, all having trifluoromethyl substitution in at least one of the 3- and the 5-position in the pyridine ring with or without additional substitution at the converse position in the pyridine ring according to the following formula, are useful as herbicidal agents: ##STR1## where the various substituents are defined herein below.

Compounds of the formula below, all having trifluoromethyl substitution in at least one of the 3- and the 5-position in the pyridine ring with or without additional substitution at the converse position in the pyridine ring according to the following formula, are useful as herbicidal agents: ##STR1## wherein the substituents are defined hereinbelow.

Trifluoromethyl pyridinylthiophenoxy propanoic acids and propanols and

Novel 2-quinolinyloxyphenoxy and 2-quinolinylthiophenoxy alkanoic acids, amides, salts, and esters thereof, and nitriles derived therefrom and 2-quinolinyloxy- and thio-phenoxy propanols and esters and ethers thereof having the following formula ##STR1## wherein: X and X' are independently F, Cl, Br, I, --CF.sub.3, CH.sub.3 O--, --NO.sub.2, or --N(R').sub.2, with the proviso that both cannot be --CF.sub.3, CH.sub.3 O--, --NO.sub.2, or --NR'.sub.2,

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Antioch, CA, United States of America

Lillian H Troxell