The Dow Chemical Company

Howard Johnston

Lillian H Troxell

Herman O Senkbeil

Alin H Gulbenk

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

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

Compounds are prepared which correspond to the formula ##STR1## wherein Y represents trichloromethyl, dichloromethyl or dichlorofluoromethyl; X represents chloro, bromo or fluoro and n represents an integer of 1 or 2. These compounds and compositions containing them have been found to be useful as agronomic fungicides, especially useful and valuable for the control of soil-borne plant disease organisms which attack the roots of plants.

Ethers of 6-halo-4-halomethylpyridines and their fungicidal compositions

Novel N-alkylaminocarbonyl-2-(4-((3-halo-5-(trifluoromethyl)-2-pyridinyl)oxy)phe noxy)propanamides provide selective control of grassy weeds in the presence of valuable crops.

Compounds and method for selectively controlling grassy weeds in

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,

Quinolinyloxyphenoxy and quinolyinylthiophenoxy alkanoic acids and

Compounds are prepared which correspond to the formula ##STR1## wherein X represents chloro, bromo or iodo; R' represents hydrogen or methyl and R represents carboxy (--COOH), the alkyl esters thereof (--COOR.sup.6 wherein R.sup.6 represents alkyl of 1 to 8 carbon atoms, (2-alkoxyethoxy)carbonyl (--COOCH.sub.2 CH.sub.2 OR.sup.2) or (1-methyl-2-alkoxyethoxy)carbonyl ##STR2## wherein R.sup.2 represents alkyl of 1 to 4 carbon atoms) or the metal salts thereof (--COOMe wherein Me represents ammonium or substituted ammonium ion (N.sup.+ H(R.sup.6).sub.3 wherein each R.sup.6 independently represents hydrogen, alkyl of 1 to 4 carbon atoms or hydroxyalkyl of 2 to 3 carbon atoms), alkali metal, alkaline earth metal, aluminum or a transition group metal); alkanoyloxymethyl (--CH.sub.2 OCOR.sup.2); (2,2-dichloropropionyloxy)methyl (--CH.sub.2 OCOC(Cl).sub.2 CH.sub.3); alkoxymethyl (--CH.sub.2 OR.sup.2); phenoxymethyl (--CH.sub.2 O.phi.); (2-alkoxyethoxy)methyl (--CH.sub.2 OCH.sub.2 CH.sub.2 OR.sup.2); hydroxyalkyl (--R.sup.3 OH wherein R.sup.3 represents alkylene of from 1 to 6 carbon atoms); 3-hydroxy-1-propenyl (--CH.dbd.CHCH.sub.2 OH); 1,2-dihydroxyethyl ##STR3## 1-(2-hydroxyethoxy)methyl (--CH.sub.2 --O--CH.sub.2 CH.sub.2 OH); (2-(2-hydroxyethoxy)ethoxy)methyl (--CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH); carbamoyl (--CONR.sup.4 R.sup.4 wherein each R.sup.4 independently represents hydrogen or alkyl of 1 to 8 carbon atoms); (carboxymethyl)carbamoyl (--CONHCH.sub.2 COOH); (2-hydroxyethyl)-carbamoyl (--CONR.sup.4 CH.sub.2 CH.sub.2 OH); or (carbamoyloxy)methyl (--CH.sub.2 OCONHR.sup.5 wherein R.sup.5 is alkyl of 1 to 4 carbon atoms or phenyl). These compounds have been found to be effective pre- and post-emergent herbicides and some as intermediates in preparing compounds which are effective pre- and post-emergent herbicides and as active agents in compositions used as herbicides.

6-Fluoro-3,5-dihalo-2-pyridyloxy compounds

Novel compounds corresponding to the formula ##STR1## and the organic or inorganic acid addition salts thereof, wherein X represents chloro, bromo or fluoro; R.sup.1 represents hydrogen, amino, loweralkylamino, arylamino, loweralkylamido or N-(loweralkyl)loweralkylamido; R.sup.2 represents hydrogen, X, amino or loweralkylamino, with the proviso that one of R.sup.1 or R.sup.2 is always amino or loweralkylamino and the other of R.sup.1 or R.sup.2 is other than amino or loweralkylamino; R represents butyl, 2-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl or the radical ##STR2## wherein Z represents amino, lower-alkylamino, phenylamino, hydroxy, loweralkoxy, aryloxy, 2-propenyl, hydroxyloweralkoxy, mercapto, loweralkylthio, loweralkanoyloxy or 2-haloloweralkanoyloxy and R.sup.3 represents hydrogen or methyl and with the proviso that R is other than butyl when R.sup.2 is X are prepared. These compounds are useful as herbicides and as active agents in compositions used as herbicides.

Substituted aminodi- or trihalopyridines and method of use

Disclosed are novel substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives, N-oxide derivatives thereof, and certain novel intermediates therefore. The compounds of the instant invention are useful as herbicides and can be formulated to provide herbicidal compositions.

Growing community of inventors

Walnut Creek, CA, United States of America

Howard Johnston