Substituted [1,2,4]triazole compounds

Patent metadata

Field	Value
Publication number	US-10450279-B2
Application number	US-201515316418-A
Country	US
Kind code	B2
Filing date	Jun 5, 2015
Priority date	Jun 6, 2014
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

1 . The present invention relates to compounds of the formula I

wherein the variables are defined in the description and claims, their preparation and uses thereof.

First claim

The invention claimed is:

1. A compound of formula I

wherein
R 1 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl;
wherein the aliphatic moieties of le are unsubstituted or carry one, two, three or up to the maximum possible number of identical or different groups R 1a :

R 1a is independently of one another selected from halogen, OH, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl and C 1 -C 4 -halogenalkoxy;
wherein the cycloalkyl moieties of R 1 are unsubstituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R 1b :

R 1b is independently of one another selected from halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl and C 1 -C 4 -halogenalkoxy;
R 2 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl;
wherein the aliphatic moieties of R 2 are unsubstituted or carry one, two, three or up to the maximum possible number of identical or different groups R 2a :

R 2a is independently of one another selected from halogen, OH, CN, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl and C 1 -C 4 -halogenalkoxy;
R 3 is halogen;
R 4 , R 5 , and R 6 are independently of one another selected from hydrogen, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -halogencycloalkyl;
wherein the aliphatic moieties of R 4 , R 5 , and R 6 are unsubstituted or further substituted by one, two, three or four of identical or different groups R a :

R a is independently of one another selected from halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenalkoxy;
wherein the cycloalkyl moieties of R 4 , R 5 , and R 6 are unsubstituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R b :

R b is independently of one another selected from halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl and C 1 -C 4 -halogenalkoxy;
X is O;
provided that at least one of R 4 , R 5 and R 6 is not hydrogen;
or an N-oxide or an agriculturally acceptable salt thereof.

2. The compound of claim 1 , wherein R 4 , R 5 , and R 6 are independently selected from hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 2 -C 4 -alkenyl, C 2 -C 3 -halogenalkenyl, unsubstituted and substituted C 2 -C 4 -alkynyl, and unsubstituted and substituted C 3 -C 6 -cycloalkyl,
wherein the aliphatic moieties of R 4 , R 5 , and R 6 are unsubstituted or further substituted by one, two, three or four R a , and
wherein the cycloalkyl moieties of R 4 , R 5 , and R 6 are unsubstituted or further substituted by one, two, three or four R b .

3. The compound of claim 1 , wherein R 4 , R 5 , and R 6 are independently selected from hydrogen, F, Cl, C 1 -C 4 -alkyl, C 1 -C 2 -halogenalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -halogenalkoxy, and cyclopropyl,
wherein the aliphatic moieties of R 4 , R 5 , and R 6 are unsubstituted or further substituted by one, two, three or four R a , and
wherein the cycloalkyl moieties of R 4 , R 5 , and R 6 are unsubstituted or further substituted by one, two, three or four R b .

4. The compound of claim 1 , wherein R a and R b are independently selected from halogen, CN, and OH.

5. The compound of claim 1 , wherein R 3 is F, Cl, or Br.

6. The compound of claim 1 , wherein R 2 is hydrogen.

7. The compound of claim 1 , wherein R 1 is selected from methyl, ethyl, n-propyl, iso-propyl, CH 2 C(CH 3 ) 3 , CH 2 CH(CH 3 ) 2 , CF 3 , C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, 1 -fluoro-cyclopropyl and 1-chloro-cyclopropyl.

8. A composition comprising one compound of formula I, as defined in claim 1 , an N-oxide or an agriculturally acceptable salt thereof.

9. The composition of claim 8 , comprising additionally a further active substance.

10. A seed coated with at least one compound of the formula I, as defined in claim 1 , and/or an agriculturally acceptable salt thereof or with a composition, as defined in claim 8 , in an amount of from 0.1 to 10 kg per 100 kg of seed.

11. A method for combating harmful 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 1 .

12. The method of claim 11 , wherein R a and R b are independently selected from halogen, CN, and OH.

13. The method of claim 11 , wherein R 3 is F, Cl, or Br.

14. The method of claim 11 , wherein R 2 is hydrogen.

15. The method of claim 11 , wherein R 1 is selected from methyl, ethyl, n-propyl, iso-propyl, CH 2 C(CH 3 ) 3 , CH 2 CH(CH 3 ) 2 , CF 3 , C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, 1 -fluoro-cyclopropyl and 1-chloro-cyclopropyl.

Assignees

• Basf Se

Inventors

• Grammenos Wassilios
• Boudet Nadege
• Mueller Bernd
• Quintero Palomar Maria Angelica
• Escribano Cuesta Ana
• Cambeis Erica May
• Lohmann Jan Klaas
• Grote Thomas
• Kretschmer Manuel
• Craig Ian Robert
• Fehr Marcus

Classifications

• C07F5/02 Primary

  Boron compounds · CPC title

• C07D249/08 Primary

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

• A01N55/08

  containing boron · CPC title

• A01N43/653

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

• A01C1/06

  Coating or dressing seed · CPC title