# US 2014/0155262 A1 · Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds

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- Number: US 2014/0155262 A1
- Document ID: US20140155262A1
- Status: Published application
- Kind: A1
- Application number: 14/131,811
- Filed: 2012-07-12
- Published: 2014-06-05
- Earliest claimed: 2011-07-13
- Assignees: BASF SE
- Inventors: Jochen Dietz; Richard Riggs; Nadege Boudet; Jan Klaas Lohmann; Ian Robert Craig; Egon Haden; Erica May Wilson Lauterwasser; Bernd Mueller; Wassilios Grammenos; Thomas Grote
- Web page: https://patentgrep.com/patent/US20140155262A1

## CPC

- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07C 43/263: the aromatic rings being non-condensed
- C07C 49/255: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07D 303/22: with monohydroxy compounds
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds of formula I as defined in the description, and the N-oxides, and salts thereof, their preparation and intermediates for preparing them. The invention also relates to the use of these compounds for combating harmful fungi and seed coated with at least one such compound and also to compositions comprising at least one such compound.

## Claims

### Claim at position 1

1-13. (canceled)

### Claim 14

A compound of formula I
wherein:
R is CF3;
R1 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl;
R2 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl;
wherein the aliphatic groups R1 and/or R2 may carry 1, 2, 3 or up to the maximum possible number of identical or different groups Ra which independently of one another are selected from the group consisting of halogen, CN, nitro, C1-C4-alkoxy and C1-C4-halogenalkoxy;
wherein the cycloalkyl and/or phenyl moieties of R1 and/or R2 may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups Rb which independently of one another are selected from the group consisting of halogen, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy;
R3 is halogen, CN, nitro, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy or C1-C4-halogenalkoxy
n is an integer and is 0, 1, 2 or 3;
R4 is halogen, CN, nitro, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy or C1-C4-halogenalkoxy
m is an integer and is 0, 1, 2, 3, 4 or 5;
and an N-oxide or an agriculturally acceptable salt thereof.

### Claim 15 (depends on 14)

The compound according to claim 14, wherein R1 is hydrogen, C1-C4-alkyl, allyl, C2-C6-alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethynyl.

### Claim 16 (depends on 14)

The compound according to claim 14, wherein R2 is hydrogen, C1-C4-alkyl, allyl, propargyl or benzyl.

### Claim 17 (depends on 14)

The compound according to claim 14, wherein m is 1, 2 or 3 and R4 is selected from F and Cl.

### Claim 18 (depends on 14)

The compound according to claim 14, wherein n=0, R2 is hydrogen, R4m is 4-Cl and R1 is selected from the group consisting of H, CH3, CH2CH3, CH2CH2CH3, CH2C≡C—CH3, CH2C≡CH, isopropyl, cyclopropyl and CF3, and compounds wherein n=0, R2 is CH3, R4m is 4-Cl and R1 is selected from H, CH3, CH2CH3, isopropyl and cyclopropyl, and the compound wherein n=0, R2 is H, R4m is 2,4-Cl2 and R1 is H, and the compound wherein n=0, R2 is H, R4m is 4-F and R1 is CH3, and the compounds wherein n=0, R1 is CH3, R4m is 4-Cl and R2 is selected from CH2CH3, and CH2CH═CH2, and the compounds wherein n=0, R1 is methyl-propargyl, R4m is 4-Cl and R2 is selected from CH2CH3, and CH2C≡CH.

### Claim 19 (depends on 14)

A process for preparing compounds of formula I as defined in claim 14, which comprises reacting a compound of formula IIIa
in presence of a catalyst with isopropylmagnesium halide followed by a reaction with R1COCl;
reacting the resulting compound of formula VIII
under basic conditions with a compound of formula II
reacting the resulting compound of formula Va
with trimethylsulf(ox)onium halide;
reacting the resulting compound of formula IX
under basic conditions with 1H-1,2,4-triazole;
and optionally derivatizing the resulting compound of formula I.A
under basic conditions with R2-LG, wherein LG is a nucleophilically replaceable leaving group, to obtain compounds of formula I.

### Claim 20 (depends on 14)

A process for preparing compounds of formula I as defined in claim 14, which comprises reacting a compound of formula IX
under acidic conditions with R2—OH,
reacting the resulting compound of formula X
with a halogenating agent or sulfonating agent;
and reacting the resulting compound of formula XI
wherein LG is a nucleophilically replaceable leaving group with 1H-1,2,4-triazole to obtain compounds I.

### Claim 21 (depends on 14)

A compound of formulae IVa, Va, VI, VII or IX
wherein R3, R4, m and n and R1, if applicable, are as defined in claim 14 and wherein X1 is I or Br, and wherein R in formulae VI, Va, VII and IX is C1-C2-halogenalkyl, with the proviso that in formula Va if R1 is hydrogen and R is CF3 and n=0, R4m is not 3-CF3 or 3-CF3-4-Cl; and wherein in formula IVa R is selected from dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, with the proviso that in formula IVa if X1 is Br, R is CF3 and n is 0, then m is not 0 and R4m is not 4-Br, 3-CF3, 4-F or 2-Cl.

### Claim 22 (depends on 14)

An agrochemical composition comprising an auxiliary and at least one compound of formula I, as defined in claim 14, an N-oxide or an agriculturally acceptable salt thereof.

### Claim 23 (depends on 22)

The compositions according to claim 22, comprising additionally a further active substance.

### Claim 24 (depends on 14)

A method for combating phytopathogenic fungi, comprising: treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I as defined in claim 14.

### Claim 25 (depends on 24)

The method of claim 24, wherein R1 is hydrogen, C1-C4-alkyl, allyl, C2-C6-alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethynyl.

### Claim 26 (depends on 24)

The method of claim 24, wherein R2 is hydrogen, C1-C4-alkyl, allyl, propargyl or benzyl.

### Claim 27 (depends on 24)

The method of claim 24, wherein m is 1, 2 or 3 and R4 is selected from F and Cl.

### Claim 28 (depends on 24)

The method of claim 24, wherein n=0, R2 is hydrogen, R4m is 4-Cl and R1 is selected from the group consisting of H, CH3, CH2CH3, CH2CH2CH3, CH2C≡C—CH3, CH2C≡CH, isopropyl, cyclopropyl and CF3, and compounds wherein n=0, R2 is CH3, R4m is 4-Cl and R1 is selected from H, CH3, CH2CH3, isopropyl and cyclopropyl, and the compound wherein n=0, R2 is H, R4m is 2,4-Cl2 and R1 is H, and the compound wherein n=0, R2 is H, R4m is 4-F and R1 is CH3, and the compounds wherein n=0, R1 is CH3, R4m is 4-Cl and R2 is selected from CH2CH3, and CH2CH═CH2, and the compounds wherein n=0, R1 is methyl-propargyl, R4m is 4-Cl and R2 is selected from CH2CH3, and CH2C≡CH.

### Claim 29 (depends on 14)

Seed coated with at least one compound of formula I as defined in claim 14, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

### Claim 30 (depends on 29)

The seed of claim 29, wherein R1 is hydrogen, C1-C4-alkyl, allyl, C2-C6-alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethynyl.

### Claim 31 (depends on 29)

The seed of claim 29, wherein R2 is hydrogen, C1-C4-alkyl, allyl, propargyl or benzyl.

### Claim 32 (depends on 29)

The seed of claim 29, wherein m is 1, 2 or 3 and R4 is selected from F and Cl.

### Claim 33 (depends on 29)

The seed of claim 29, wherein n=0, R2 is hydrogen, R4m is 4-Cl and R1 is selected from the group consisting of H, CH3, CH2CH3, CH2CH2CH3, CH2C≡C—CH3, CH2C≡CH, isopropyl, cyclopropyl and CF3, and compounds wherein n=0, R2 is CH3, R4m is 4-Cl and R1 is selected from H, CH3, CH2CH3, isopropyl and cyclopropyl, and the compound wherein n=0, R2 is H, R4m is 2,4-Cl2 and R1 is H, and the compound wherein n=0, R2 is H, R4m is 4-F and R1 is CH3, and the compounds wherein n=0, R1 is CH3, R4m is 4-Cl and R2 is selected from CH2CH3, and CH2CH═CH2, and the compounds wherein n=0, R1 is methyl-propargyl, R4m is 4-Cl and R2 is selected from CH2CH3, and CH2C≡CH.