5-iodotriazole derivatives
View Patent ↗The present invention relates to novel 5-iodotriazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.
1. A compound of formula (I):
or an agrochemically active salt thereof,
in which
X is OR 1 , CN or hydrogen,
Y is O, S, SO, SO 2 , —CH 2 — or a direct bond,
m is 0 or 1,
n is 0 or 1,
R is in each case optionally branched C 3 -C 7 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 3 -alkyl, tri(C 1 -C 3 -alkyl)silyl-C 1 -C 3 -alkyl, in each case optionally 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-, C 1 -C 4 -alkylthio- or phenoxy-substituted (where phenoxy may be substituted by halogen or C 1 -C 4 -alkyl) C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, where any substitution is on the cycloalkyl moiety,
R 1 is hydrogen, optionally substituted alkylcarbonyl or trialkylsilyl,
R and R 1 together are optionally halogen-, alkyl- or haloalkyl-substituted C 1 -C 4 -alkylene or C 1 -C 4 -alkyleneoxy, where the oxygen of this group is joined to R,
R 2 is hydrogen, halogen or optionally substituted alkyl, or
when n is 1, and X is OR 1 , then R 1 and R 2 taken together can form a direct bond,
R 3 is hydrogen, halogen or optionally substituted alkyl, and
A is optionally substituted aryl.
2. The compound or the salt of formula (I) according to claim 1 , in which
X is OR 1 ,
Y is O, S, SO 2 , —CH 2 — or a direct bond,
m is 0 or 1,
n is 0 or 1,
R is in each case optionally branched C 3 -C 7 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 7 -alkenyl, C 2 -C 7 -haloalkenyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 3 -alkyl, tri(C 1 -C 3 -alkyl)silyl-C 1 -C 3 -alkyl, in each case optionally halogen-, C 1 -C 4 -haloalkyl-, C 1 -C 4 alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylthio- or phenoxy-substituted C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl where any substitution is on the cycloalkyl moiety,
R 1 is hydrogen, (C 1 -C 3 -alkyl)carbonyl, (C 1 -C 3 -haloalkyl)carbonyl or tri(C 1 -C 3 -alkyl)silyl, or
R and R 1 together are optionally fluorine-, chlorine-, bromine-, C 1 -C 4 -alkyl- or C 1 -C 4 -haloalkyl-substituted —(CH 2 ) 3 —, —CH 2 O—, —(CH 2 ) 2 O—, —(CH 2 ) 3 O—, where the oxygen of this group is in each case joined to R,
R 2 is hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, or
when n is 1, and X is OR′, then R′ and R 2 taken together can form a direct bond,
R 3 is hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl,
A is unsubstituted or mono- to tri-Z 1 -substituted phenyl, where
Z 1 is halogen, cyano, nitro, OH, SH, C(alkyl)(═NOalkyl), C 3 -C 7 -cycloalkyl, C 1 -C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, formyl, C 2 -C 5 -alkylcarbonyl, C 2 -C 5 -haloalkylcarbonyl, C 2 -C 5 -alkoxycarbonyl, C 2 -C 5 -haloalkoxycarbonyl, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 2 -C 5 -alkylcarbonyloxy, C 2 -C 5 -haloalkylcarbonyloxy, trialkylsilyl, or in each case optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy- or C 2 -C 4 -alkylcarbonyl-monosubstituted phenyl, phenoxy or phenylthio.
3. The compound of claim 1 , wherein n is 1, X is OR 1 , and R and OR 1 taken together form an optionally halogen-, alkyl-, or haloalkyl-substituted tetrahydrofuran-2-yl, 1,3-dioxetan-2-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, or 1,3-dioxepan-2-yl ring.
4. The compound of claim 2 , wherein n is 1, X is OR 1 , and R and OR 1 taken together form an optionally fluorine-, chlorine-, bromine-, C 1 -C 4 -alkyl-, or C 1 -C 4 -haloalkyl-substituted tetrahydrofuran-2-yl, 1,3-dioxetan-2-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, or 1,3-dioxepan-2-yl ring.
5. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (I) according to claim 1 or 2 , and one or more extenders and/or one or more surfactants.
6. A process for producing a composition for controlling phytopathogenic harmful fungi, comprising mixing at least one compound of formula (I) according to claim 1 or 2 with one or more extenders and/or one or more surfactants.
7. A method for controlling phytopathogenic harmful fungi, comprising applying at least one compound of formula (I) according to claim 1 or 2 to the phytopathogenic harmful fungi and/or their habitat.
8. A method for regulating plant growth comprising applying at least one compound of formula (I) according to claim 1 or 2 to a plant.
9. A method for treating transgenic plants comprising contacting said plants with at least one compound of formula (I) according to claim 1 .
10. A method for treating seeds comprising contacting said seeds with at least one compound of formula (I) according to claim 1 .
11. The method according to claim 10 , wherein said seeds are seeds of transgenic plants.