Heterocyclic alkanol derivatives
The present invention relates to novel heterocyclic alkanol derivatives, to processes for preparing these compounds, to compositions comprising these compounds and to their use as biologically active compounds, in particular for controlling harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.
1. A compound of formula (I)
in which
X is O or S,
Y is O,
m is 0 or 1,
n is 0 or 1,
R is alkyl, alkenyl, cycloalkyl or aryl, each of which is optionally substituted,
R 1 is hydrogen, SH, alkylthio, alkoxy, halogen, haloalkyl, haloalkylthio, haloalkoxy, cyano, nitro or Si(alkyl) 3 ,
A is optionally substituted heteroaryl,
and salts thereof.
2. The compound of claim 1 , in which
X is S,
Y is O,
m is 0 or 1,
n is 0 or 1,
R is optionally branched C 3 -C 7 -alkyl; optionally branched C 1 -C 8 -haloalkyl; optionally branched C 2 -C 7 -alkenyl; optionally branched C 2 -C 7 -haloalkenyl; C 3 -C 7 -cycloalkyl which may be optionally substituted with halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -alkylthio; or phenyl which is optionally substituted with mono-halogen, di-halogen, tri-halogen, or C 1 -C 4 -alkyl,
R 1 is hydrogen, SH, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy or halogen,
A is a mono- or poly-Z 1 -substituted five- or six-membered heteroaryl selected from the group consisting of furyl, thienyl, pyrrolyl pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and triazinyl, where
Z 1 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -halothioalkyl, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, or phenyl, phenoxy or phenylthio each of which is optionally substituted with halogen or C 1 -C 4 -alkyl.
3. A composition for controlling phytopathogenic harmful fungi, comprising the compound of claim 1 and an extender, a surfactant, or combinations thereof.
4. The composition of claim 3 , further comprising at least one active ingredient selected from the group consisting of insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners, and semiochemicals, and combinations thereof.
5. A process for producing the composition of claim 3 , comprising mixing the compound of claim 1 with an extender, a surfactant, or combinations thereof.
6. The compound of claim 1 , wherein
X is S,
Y is O,
m is 0,
n is 0,
R is tert-butyl, isopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl, 1-methylthiocyclopropyl, 1-trifluoromethylcyclopropyl, (3E)-4-chloro-2-methylbut-3-en-2-yl, or C 1 -C 4 -haloalkyl,
R 1 is hydrogen, SH, methylthio, ethylthio, methoxy, ethoxy, fluorine, chlorine, bromine, or iodine,
A is a mono- or poly-Z 1 -substituted five or six-membered heteroaryl selected from the group consisting of 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1, 2,3-triazol-5-yl, 1H-1,2,4-triazol- 3-yl, 1H-1,2,4-triazol-5-yl, 1H-1,2,4-triazol-1-yl, 1H-tetrazol-1-yl, 1H-tetrazol-5yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, and 2-pyrazinyl, and
Z 1 is fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trichloromethyl, difluoromethyl, difluoromethoxy, difluoromethylthio, dichloromethyl, difluorochloromethyl, or difluorochloromethoxy.
7. The compound of claim 1 , wherein said compound is selected from the group consisting of:
8. A method of treating a plant from fungal infection comprising applying the compound according to claim 1 to a plant seed, a plant, parts of a plant, fruit of a plant, soil surrounding a plant, or combinations thereof.