Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl/alkenyl-ethyl}-1H-[1,2,4]triazole compounds

Patent metadata

Field	Value
Publication number	US-9247747-B2
Application number	US-201214237470-A
Country	US
Kind code	B2
Filing date	Aug 14, 2012
Priority date	Aug 15, 2011
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

The present invention relates to substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl-ethyl}-1H-[1,2,4]triazole compounds of formula I as defined in the description, and the N-oxides, and salts thereof, processes and intermediates for preparing these compounds and also to compositions comprising at least one such compound. The invention also relates to the use of such compounds and compositions for combating harmful fungi and seed coated with at least one such compound.

First claim

The invention claimed is:

1. A compound of formula I

wherein:
X 1 , X 2 independently of each other are selected from halogen;
R 1 is C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl; wherein the aliphatic moieties of R 1 may carry 1, 2 or 3 R a , independently selected from CN, C 1 -C 2 -alkoxy and C 1 -C 2 -halogenalkoxy;
R 2 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl;
wherein the aliphatic moieties of R 2 may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R a which independently of one another are selected from the group consisting of halogen, CN, nitro, phenyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy,
wherein the phenyl may be be substituted by 1, 2, 3, 4 or 5 substituents selected from halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl and C 1 -C 4 -halogenalkoxy;
wherein the cycloalkyl and/or phenyl moieties of R 2 may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R b which independently of one another are selected from the group consisting of halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl and C 1 -C 4 -halogenalkoxy;

or an N-oxide or an agriculturally acceptable salt thereof.

2. The compound of claim 1 , wherein X 1 is Cl.

3. The compound of claim 1 , wherein X 2 is Cl.

4. The compound of claim 1 , wherein R 1 is C 2 -C 4 -alkenyl.

5. The compound of claim 1 , wherein R 1 is C 2 -C 6 -alkynyl.

6. The compound of claim 1 , wherein R 1 is unsubstituted.

7. The compound of claim 1 , wherein R 2 is C 1 -C 4 -alkyl.

8. The compound of claim 1 , wherein X 1 and X 2 are Cl, R 1 is C≡CH and R 2 is CH 3 , C 2 H 5 , CH 2 C≡CH, CH 2 C 6 H 5 , or CH 2 CH 2 CH 3 ; and compounds wherein X 1 and X 2 are Cl, R 1 is CH═CH 2 and R 2 is CH 3 , CH 2 CH═CH 2 , or CH 2 C≡CH; and compounds wherein X 1 and X 2 are Cl, R 1 is C≡CCH 3 and R 2 is CH 3 , C 2 H 5 , CH 2 CH═CH 2 , CH 2 C≡CH or CH 2 C(Cl)═CHCl; and compounds wherein X 1 and X 2 are Cl, R 1 is CH 2 C≡CH and R 2 is CH 2 C≡CH.

9. A process for preparing compounds of formula I as defined in claim 1 , which comprises reacting a compound of formula IIIA

wherein Y is F or Cl and X 3 is I or Br, with a halo-phenole of formula II

under basic conditions; reacting the resulting compound of formula IVa

with isopropylmagnesium bromide followed by a reaction with acetyl chloride;
halogenating the resulting compound of formula V

reacting the resulting compound of formula VI

wherein Hal stands for halogen, under basic conditions with 1H-1,2,4-triazole;
reacting the resulting compound of formula VII

with R 1 -M, wherein M is MgBr, MgCl, Li or Na; and reacting the resulting compound of VIII

under basic conditions with R 2 -LG, wherein LG is a nucleophilically replaceable leaving group, to obtain compounds of formula I.

10. A process for preparing compounds of formula I as defined in claim 1 , which comprises reacting a compound of formula IIIa

wherein Y is F or Cl and X 3 is I or Br; with isopropylmagnesium halide followed by a reaction with a compound of formula IX R 1 —COCl;
converting the resulting compound of formula X

wherein Y is F or Cl; under basic conditions with a halo-phenole of formula II

reacting the resulting compound of formula Va

with trimethylsulf(ox)onium halide; reacting the resulting compound of formula XI

under basic conditions with 1H-1,2,4-triazole; and reacting the resulting compound of formula VIII

under basic conditions with R 2 -LG, wherein LG is a nucleophilically replaceable leaving group, to obtain compounds of formula I.

11. A process for preparing compounds of formula I as defined in claim 1 , which comprises reacting a compound of formula XI

under acidic conditions with R 2 —OH; reacting the resulting compound of formula XII

with a halogenating agent or sulfonating agent; reacting the resulting compound of formula XIII

wherein LG is a nucleophilically replaceable leaving group with 1H-1,2,4-triazole, to obtain compounds I.

12. An agrochemical composition comprising an auxiliary and at least one compound of claim 1 , an N-oxide or an agriculturally acceptable salt thereof.

13. Seed coated with at least one compound of claim 1 , in an amount of from 0.1 g to 10 kg per 100 kg of seed.

14. A method for controlling phytopathogenic harmful fungi, which comprises treating the fungi, their habitat or the plants to be protected against fungal attack, the soil or seeds with a compound of claim 1 .

15. The method of claim 14 , wherein X 1 is Cl.

16. The method of claim 14 , wherein X 2 is Cl.

17. The method of claim 14 , wherein R 1 is C 2 -C 4 -alkenyl.

18. The method of claim 14 , wherein R 1 is C 2 -C 6 -alkynyl.

Assignees

• Dietz Jochen
• Riggs Richard
• Boudet Nadege
• Lohmann Jan Klaas
• Craig Ian Robert
• Haden Egon
• Lauterwasser Erica May Wilson
• Müller Bernd
• Grammenos Wassilios
• Grote Thomas
• Basf Se

Inventors

• Dietz Jochen
• Riggs Richard
• Boudet Nadege
• Lohmann Jan Klaas
• Craig Ian Robert
• Haden Egon
• Lauterwasser Erica May Wilson
• Müller Bernd
• Grammenos Wassilios
• Grote Thomas

Classifications

• C07D249/08 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• A01N43/653 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D303/22

  with monohydroxy compounds · CPC title