Substituted pyridine compounds

A herbicidal composition comprising an adjuvant and an effective amount of a compound represented by the formula ##STR15## wherein:

• R.sub.1 is fluorinated methyl, chlorofluorinated methyl or fluorinated ethyl;
• R.sub.2 is hydrogen, C1-C7 alkyl, trichloromethyl, C2-C8 cyanoalkyl, C3-C7 alkenyl, or C3-C7 alkynyl;
• R is C1-C6 straight or branched alkyl, C1-C7 haloalkyl, C2-C14 alkylthioalkyl, C2-C14 alkoxyalkyl, C2-C8 carboxyalkyl, C3-C4 cycloalkyl, or cyclopropylmethyl;
• X and Y are independently selected from ##STR16## 1-pyrrolyl;
• cyano;
• 4,5-dihydro-2-oxazolyl;
• NR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are independently hydrogen or hydroxyalkyl;
• 4,5-dihydro-2-thiazolyl;
• C2-C8 alkoxymethyleneamino;
• dialkylaminomethyleneamino;
• alkylthiomethyleneamino;
• tetrahydro-4-methylene-5-oxo-2-furanyl;
• 1 3-dithiolan-2-yl, 1,3-dioxolan-2-yl;
• 1,3-dithian-2-yl;
• (2-hydroxyalkyl) iminomethyl;
• halo-2-(haloalkyl) iminomethyl;
• 5,6-dihydro-4H-1,3-thiazin-2-yl;
• 5,6-dihydro-4H-1, 3-oxazin-2-yl;
• 1,3,4-oxadiazol-2-yl;
• 1,3-dioxan-2-yl;
• 5-oxazolyl;
• hydroxyalkyl;
• 2-oxazolyl;
• halo-1-oxoalkylamino;
• (dihydro-2(3H)-furanylidene) amino;
• 1,3-oxathiolan-2-yl;
• 4-oxo-1,3-dioxolan-2-yl;
• 3-oxathiolan-2-yl;
• 3,3-dioxo-1,3-oxathiolan-2-yl;
• and 2-thiazole;
• provided that 1 of X and Y contains a heterocycle;
• or
• one of X and Y is selected from ##STR17## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl and where Z is 1-pyrazolyl;
• 1-imidazolyl;
• 1,2,4-triazolyl;
• 1-pyrrolidinyl;
• 1-piperidinyl;
• 1-azetidinyl;
• 4-morpholinyl;
• 4-thiomorpholinyl;
• 3-thiazolidinyl;
• 1-aziridinyl;
• hexahydro-1-azepinyl;
• or 2-isoxazolidinyl;
• and
• the other of X and Y is selected from
• 4. 5-dihydro-2-oxazolyl;
• 4,5-dihydro-2-thiazolyl;
• tetrahydro-4-methylene-5-oxo-2-furanyl;
• 1 3-dithiolan-2-yl, 1,3-dioxolan-2-yl;
• 1,3-dithian-2-yl;
• 5,6-dihydro-4H-1,3-thiazin-2-yl;
• 5,6-dihydro-4H-1,3-oxazin-2-yl;
• 1,3,4-oxadiazol-2-yl;
• 1,3-dioxan-2-yl;
• 5-oxazolyl;
• hydroxyalkyl;
• 2-oxazolyl;
• halo-1-oxoalkylamino;
• (dihydro-2(3H)-furanylidene) amino;
• 1,3-oxathiolan-2-yl;
• 4-oxo-1,3-dioxolan-2-yl;
• 3-oxathiolan-2-yl;
• 3,3-dioxo-1,3-oxathiolan-2-yl;
• and 2-thiazole;
• or
• X and Y are independently selected from
• the above-mentioned heterocycles substituted by one or more substituents selected from halo;
• nitro;
• acetylamino;
• amino;
• and cyano;
• or
• one of X and Y is selected from ##STR18## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl and where Z is hydrogen;
• halogen;
• hydroxy;
• C1-C7 alkoxy;
• C1-C7 haloalkoxy;
• C3-C7 alkynyloxy:
• C1-C7 alkylthio NR.sub.4 R.sub.5 where R.sub.4 and R.sub.5 are independently hydrogen or lower alkyl:
• acetylamino;
• C1-C7 hydroxyalkyl;
• C1-C7 haloalkyl;
• C.sub.2 -C.sub.8 alkoxymethyleneamino;
• 1-pyrazolyl;
• 1-imidazolyl;
• 1,2,4-triazolyl;
• 1-pyrrolidinyl;
• 1-piperidinyl;
• 1-azetidinyl;
• 4-morpholinyl;
• 4-thiomorpholinyl;
• 3-thiazolidinyl;
• 1-aziridinyl;
• hexahydro-1-azepinyl;
• C2-C8 alkoxymethyleneamino;
• and 2-isoxazolidinyl;
• and the other of X and Y is selected from
• 1-pyrrolyl;
• 4,5-dihydro-2-oxazolyl;
• 4,5-dihydro-2-thiazolyl;
• tetrahydro-4-methylene-5-oxo-2-furanyl;
• 1 3-dithiolan-2-yl, 1,3-dioxolan-2-yl;
• 1,3-dithian-2-yl;
• 5,6-dihydro-4H-1,3-thiazin-2-yl;
• 5,6-dihydro-4H-1, 3-oxazin-2-yl;
• 1,3,4-oxadiazol-2-yl;
• 1,3-dioxan-2-yl;
• 5-oxazolyl;
• hydroxyalkyl;
• 2-oxazolyl;
• halo-1-oxoalkylamino;
• (dihydro-2(3H)-furanylidene) amino;
• 1,3-oxathiolan-2-yl;
• 4-oxo-1,3-dioxolan-2-yl;
• 3-oxathiolan-2-yl;
• 3,3-dioxo-1,3-oxathiolan-2-yl;
• and 2-thiazole;
• wherein the above-mentioned heterocycles are unsubstituted or substituted with one or more substituents selected from C1-C7 alkyl, halo, nitro, acetylamino, amino, and cyano;
• provided that when one of X and Y is ##STR19## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl;
• and Z is hydrogen;
• halogen;
• hydroxy;
• C1-C7 alkoxy;
• C1-C7 haloalkoxy;
• C3-C7 alkynyloxy;
• C-1-C7 alkylthio;
• NR.sub.4 R.sub.5 where R.sub.4 and R.sub.5 independently hydrogen or lower alkyl;
• acetylamino;
• C1-C7 hydroxyalky;
• C1-C7 haloalkyl;
• or C2-C8 alkoxymethyleneamino:
• or is 1 3-dithiolan-2-yl, 1 3-dithiolan-2-yl;
• 1,3-dioxolan-2-yl 1,3-dioxan-2-yl 1,3-oxothiolan-2-yl 4-oxo-1,3-dioxolan-2-yl;
• or 3,3-dioxo-1,3-oxathiolan-2 yl, the other is not ##STR20## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl;
• and Z is hydrogen;
• halogen;
• hydroxy;
• C1-C7 alkoxy;
• C1-C7 haloalkoxy;
• C3-C7 alkynyloxy;
• C1-C7 alkylthio;
• NR.sub.4 R.sub.5 where R.sub.4 and R.sub.5 are independently hydrogen or lower alkyl;
• acetylamino;
• C1-C7 hydroxyalkyl;
• C1-C7 haloalkyl;
• C2-C8 alkoxymethyleneamino or 1-pyrazolyl.

A method of controlling undesirable vegetation comprising applying to the soil an effective herbicidal amount of a compound represented by the formula ##STR21## wherein:

• R.sub.1 is fluorinated methyl, chlorofluorinated methyl or fluorinated ethyl;
• R.sub.2 is hydrogen, C1-C7 alkyl, trichloromethyl, C2-C8 cyanoalkyl, C3-C7 alkenyl, or C3-C7 alkynyl;
• R is C1-C6 straight or branched alkyl, C1-C7 haloalkyl, C2-C14 alkylthioalkyl, C2-C14 alkoxyalkyl, C2-C8 carboxyalkyl, C3-C4 cycloalkyl, or cyclopropylmethyl;
• X and Y are independently selected from ##STR22## 1-pyrrolyl;
• cyano;
• 4,5-dihydro-2-oxazolyl;
• NR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are independently hydrogen or hydroxyalkyl;
• 4,5-dihydro-2-thiazolyl;
• C2-C8 alkoxymethyleneamino;
• dialkylaminomethyleneamino;
• alkylthiomethyleneamino;
• tetrahydro-4-methylene-5-oxo-2-furanyl;
• 1 3-dithiolan-2-yl, 1,3-dioxolan-2-yl;
• 1,3-dithian-2-yl;
• (2-hydroxyalkyl) iminomethyl;
• halo-2-(haloalkyl) iminomethyl;
• 5,6-dihydro-4H-1,3-thiazin-2-yl;
• 5,6-dihydro-4H-1,3-oxazin-2-yl;
• 1,3,4-oxadiazol-2-yl;
• 1,3-dioxan-2-yl;
• 5-oxazolyl;
• hydroxyalkyl;
• 2-oxazolyl;
• halo-1-oxoalkylamino;
• (dihydro-2(3H)-furanylidene) amino;
• 1,3-oxathiolan-2-yl;
• 4-oxo-1,3-dioxolan-2-yl;
• 3-oxathiolan-2-yl;
• 3,3-dioxo-1,3-oxathiolan-2-yl;
• and 2-thiazole;
• provided that 1 of X and Y contains a heterocycle;
• or
• one of X and Y is selected from ##STR23## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl and where Z is 1-pyrazolyl;
• 1-imidazolyl;
• 1 2,4-triazolyl;
• 1-pyrrolidinyl;
• 1-piperidinyl;
• 1-azetidinyl;
• 4-morpholinyl;
• 4-thiomorpholinyl;
• 3-thiazolidinyl;
• 1-aziridinyl;
• hexahydro-1-azepinyl;
• or 2-isoxazolidinyl;
• and
• the other of X and Y is selected from
• 4. 5-dihydro-2-oxazolyl;
• 4,5-dihydro-2-thiazolyl;
• tetrahydro-4-methylene-5-oxo-2-furanyl;
• 1 3-dithiolan-2-yl, 1,3-dioxolan-2-yl;
• 1,3-dithian-2-yl;
• 5,6-dihydro-4H-1,3-thiazin-2-yl;
• 5,6-dihydro-4H-1,3-oxazin-2-yl;
• 1,3,4-oxadiazol-2-yl;
• 1,3-dioxan-2-yl;
• 5-oxazolyl;
• hydroxyalkyl;
• 2-oxazolyl;
• halo-1-oxoalkylamino;
• (dihydro-2(3H)-furanylidene) amino;
• 1,3-oxathiolan-2-yl;
• 4-oxo-1,3-dioxolan-2-yl;
• 3-oxathiolan-2-yl;
• 3,3-dioxo-1,3-oxathiolan-2-yl;
• and 2-thiazole;
• or
• X and Y are independently selected from
• the above-mentioned heterocycles substituted by one or more substituents selected from nitro;
• acetylamino;
• amino;
• and cyano;
• or
• one of X and Y is selected from ##STR24## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl and where Z is hydrogen;
• halogen;
• hydroxy;
• C1-C7 alkoxy;
• C1-C7 haloalkoxy;
• C3-C7 alkynyloxy;
• C1-C7 alkylthio;
• NR.sub.4 R.sub.5 where R.sub.4 and R.sub.5 are independently hydrogen or lower alkyl:
• acetylamino;
• C1-C7 hydroxyalkyl;
• C1-C7 haloalkyl;
• C.sub.2 -C.sub.8 alkoxymethyleneamino;
• 1-pyrazolyl;
• 1-imidazolyl;
• 1,2,4-triazolyl;
• 1-pyrrolidinyl;
• 1-piperidinyl;
• 1-azetidinyl;
• 4-morpholinyl;
• 4-thiomorpholinyl;
• 3-thiazolidinyl;
• 1-aziridinyl;
• hexahydro-1-azepinyl;
• C2 C8 alkoxymethyleneamino;
• and 2-isoxazolidinyl;
• and the other of X and Y is selected from
• 1-pyrrolyl;
• 4,5-dihydro-2-oxazolyl;
• 4,5-dihydro-2-thiazolyl;
• tetrahydro-4-methylene-5-oxo-2-furanyl;
• 1 3-dithiolan-2-yl, 1,3-dioxolan-2-yl;
• 1,3-dithian-2-yl;
• 5,6-dihydro-4H-1,3-thiazin-2-yl;
• 5,6-dihydro-4H-1,3-oxazin-2-yl;
• 1,3,4-oxadiazol-2-yl;
• 1,3-dioxan-2-yl;
• 5-oxazolyl;
• hydroxyalkyl;
• 2-oxazolyl;
• halo-1-oxoalkylamino;
• (dihydro-2(3H)-furanylidene) amino;
• 1,3-oxathiolan-2-yl;
• 4-oxo-1,3-dioxolan-2-yl;
• 3-oxathiolan-2-yl;
• 3,3-dioxo-1,3-oxathiolan-2-yl;
• and 2-thiazole;
• wherein the abovementioned heterocycles are unsubstituted or substituted with one or more substituents selected from C1-C7 alkyl, halo, nitro, acetylamino, amino, and cyano;
• provided that when one of X and Y is ##STR25## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl;
• and Z is hydrogen;
• halogen;
• hydroxy;
• C1-C7 alkoxy;
• C1-C7 haloalkoxy;
• C3-C7 alkynyloxy;
• C1-C7 alkylthio;
• NR.sub.4 R.sub.5 where R.sub.4 and R.sub.5 independently hydrogen or lower alkyl;
• acetylamino;
• C1-C7 hydroxyalky;
• C1-C7 haloalkyl;
• or C2-C8 alkoxymethyleneamino:
• or is 1 3-dithiolan-2-yl, 1 3-dithiolan-2-yl;
• 1,3-dioxolan-2-yl 1,3-dioxan-2-yl 1,3-oxothiolan-2-yl 4-oxo-1,3-dioxolan-2-yl;
• or 3,3-dioxo-1,3-oxathiolan-2 yl, the other is not ##STR26## where Z.sub.1 is oxygen or NR.sub.3 where R.sub.3 is lower alkyl;
• and Z is hydrogen;
• halogen;
• hydroxy;
• C1-C7 alkoxy;
• C1-C7 haloalkoxy;
• C3-C7 alkynyloxy;
• C1-C7 alkylthio;
• NR.sub.4 R.sub.5 where R.sub.4 and R.sub.5 are independently hydrogen or lower alkyl;
• acetylamino;
• C1-C7 hydroxyalkyl;
• C1-C7 haloalkyl;
• C2-C8 alkoxymethyleneamino or 1-pyrazolyl.