Use of substituted oxadiazoles for combating phytopathogenic fungi

• US 10,118,906 B2
• Filed: 06/01/2015
• Issued: 11/06/2018
• Est. Priority Date: 06/06/2014
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Wieja, Andy, Winter, Christian, Rosenbaum, Claudia, Kremzow-Graw, Doris, Roehl, Franz, Rheinheimer, Joachim, Poonoth, Manojkumar, Terteryan, Violeta, Haden, Egon, Escribano Cuesta, Ana, Achenbach, Janosch Harald, Mentzel, Tobias, Wiebe, Christine
• Primary Examiner(s): Weddington, Kevin E
• Application Number:
  US15/316,399
• Publication Number:
  US 20170144980A1
• Time in Patent Office: 1,254 Days
• Field of Search: 514364
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: C07D 271/06 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 413/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems

Abstract

The present invention relates to the use of novel oxadiazoles of the formula I or an N-oxide and/or their agriculturally useful salts for controlling phytopathogenic fungi, or to a method for combating phytopathogenic harmful fungi, which process comprises 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 or an N-oxide or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one such compound and to agrochemical compositions further comprising seeds.

Claims

1. An agrochemical composition comprising an auxiliary and a compound of formula I

2. The composition of claim 1, wherein A is phenyl.

3. The composition of claim 1, wherein Y is O.

4. The composition of claim 1, wherein R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl and R² is phenyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl, phenyl or heteroaryl;

and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and

wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R^1a.

5. The composition of claim 4, wherein W is NR¹R² and wherein R¹ and R² independently of each other are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl;

and wherein the alicyclic and the cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R^1a.

6. The agrochemical composition according to claim 1 further comprising at least one further pesticidally active substance.

7. The agrochemical composition according to claim 1 further comprising seed, wherein the amount of the compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, is from 0.1 g to 10 kg per 100 kg of seed.

8. A method for combating phytopathogenic harmful fungi comprising treating fungi or materials, plants, soil or seeds to be protected against fungal attack, with an effective amount of the composition of claim 1.

9. The method of claim 8, wherein A is phenyl.

10. The method of claim 8, wherein Y is O.

11. The method of claim 8, wherein R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl and R² is phenyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl, phenyl or heteroaryl;

and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and

wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R^1a.

12. The method of claim 8, wherein R¹ and R² independently of each other are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl;

and wherein the alicyclic and the cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R^1a.

13. The composition of claim 1, wherein R¹ is hydrogen and R² is phenyl;

and wherein the phenyl group is unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R^1a; and

wherein R^1a is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy or C₃-C₈-cycloalkyl.

14. The composition of claim 1, wherein R¹ is hydrogen and R² heteroaryl-C₁-C₄-alkyl;

and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a; and

wherein R1a is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy or C₃-C₈-cycloalkyl.

15. The method of claim 8, R¹ is hydrogen and R² is phenyl;

and wherein the phenyl group is unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R^1a; and

wherein R^1a is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy or C₃-C₈-cycloalkyl.

16. The method of claim 8, wherein R¹ is hydrogen and R² heteroaryl-C₁-C₄-alkyl;

and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a; and

wherein R1a is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy or C₃-C₈-cycloalkyl.