IP Library Granted Patent US 12,653,191
Granted Patent B2
US 12,653,191 · App. 18/010,752 · Granted Jun 16, 2026

Active compound combinations

Inventors: Agostinos Michael Klüken (Krefeld, DE); Julie Geist (Lyons, FR); Cyril Montagne (Lyons, FR); Anthony Millet (Tignieu-jameyzieu, FR); Lionel Nicolas (Lyons, FR); Tomoki Tsuchiya (Lyons, FR)
Assignee: BAYER AKTIENGESELLSCHAFT
A01N43/88A01P3/00
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Quick Facts
Patent No.
US 12,653,191
App. No.
18/010,752
Granted
Jun 16, 2026
Kind
B2
Abstract

The present invention relates to active compound combinations, in particular within a fungicide composition, which comprise as compound (A) a compound of formula (I) and as compound (B) a further fungicidally active compound as specified below. Moreover, the invention relates to compositions comprising such compound combination and to the use of the compound combinations and the fungicide compositions as biologically active agent, especially for control of phytopathogenic fungi in crop protection and in the protection of industrial materials and as plant growth regulators.

Claims (16)

1 . An active compound combination comprising

(A) at least one compound selected from the group consisting of (I-052) rac-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (I-130) (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, (I-300) rac-5-[(4-bromo-2-methylphenyl)methyl]-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine, (I-302) rac-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (I-337) (5S)-5-[(4-bromo-2-methylphenyl)methyl]-3-[3-(3-chloro-2-fluorophenoxy)-6-methyl-pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine, (I-338) (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine and (I-339) (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methyl-pyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine,

and

(B) at least one further active compound selected from the group consisting of (1.002) difenoconazole, (1.018) prothioconazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.055) mefentrifluconazole, (1.062) fluoxytioconazole, (1.067) N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyl-imido-formamide, (2.002) bixafen, (2.005) fluopyram, (2.028) inpyrfluxam, (2.038) isoflucypram, (3.020) trifloxystrobin, (3.025) fenpicoxamid, (5.003) captan, (5.010) dithianon, (5.012) folpet, (5.013) mancozeb, (5.018) propineb, (6.002) isotianil, (7.005) pyrimethanil, (13.001) fludioxonil, (13.004) proquinazid, (13.005) quinoxyfen, (15.012) fosetyl-aluminium, (15.016) metrafenone, (15.043) fluoxa¬piprolin and (15.064) (N′-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide), (17.001) Bacillus subtilis strain QST713/AQ713 having NRRL Accession No. B-21661 (17.012) a Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129 and (18.001) a composition comprising one or more fatty acids or derivatives thereof selected from unsaturated and saturated C 12 -C 24 fatty acids, salts thereof, esters thereof or mixtures of any of the foregoing, wherein at least 95% of said fatty acids or derivatives thereof are in the range of C 14 to C 20 .

2 . The active compound combination according to claim 1 , wherein the at least one compound is selected from the group consisting of (I-302) rac-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (I-338) (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine and (I-339) (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

3 . The active compound combination according to claim 1 , wherein the at least one further active compound is selected from the group consisting of (1.002) difenoconazole, (1.018) prothioconazole, (1.020) spiroxamine, (1.055) mefentrifluconazole, (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl) propyl]-3-pyridyl]oxy] benzonitrile, (1.092) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl) propanoate, (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.007) fluxapyroxad, (2.009) Isofetamid, (2.028) inpyrfluxam, (2.030) fluindapyr, (2.038) isoflucypram, (3.012) fluoxastrobin, (3.020) trifloxystrobin, (3.025) fenpicoxamid, (3.030) metyltetraprole, (3.031) florylpicoxamid, (3.032) (2S,3S)-3-(0-tolyl) butan-2-yl N-{[4-methoxy-3-(propanoyloxy)-2-pyridyl]carbonyl}-L-alaninate, (7.005) pyrimethanil, (12.004) metalaxyl-M (mefenoxam), (13.001) fludioxonil, (13.004) proquinazid, (15.012) fosetyl-aluminium, (15.016) metrafenone and (15.043) fluoxapiprolin.

4 . The active compound combination according to claim 1 , wherein the at least one further active compound is selected from the group consisting of (1.002) difenoconazole, (1.018) prothioconazole, (1.020) spiroxamine, (1.055) mefentrifluconazole, (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl) propyl]-3-pyridyl] oxy] benzonitrile, (1.092) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl) propanoate, (2.002) bixafen, (2.007) fluxapyroxad, (2.009) Isofetamid, (2.028) inpyrfluxam, (2.038) isoflucypram, (3.020) trifloxystrobin, (3.025) fenpicoxamid, (3.030) metyltetraprole, (3.031) florylpicoxamid, (3.032) (2S,3S)-3-(o-tolyl) butan-2-yl N-{[4-methoxy-3-(propanoyloxy)-2-pyridyl]carbonyl}-L-alaninate and (7.005) pyrimethanil.

5 . A composition for controlling harmful microorganisms, in crop protection and in the protection of materials, comprising an active compound combination according to claim 1 , in addition to at least one extender and/or surfactant.

6 . A method for controlling harmful microorganisms, in crop protection and in the protection of materials, comprising applying an active compound combination according to claim 1 to the harmful microorganisms and/or their habitat.

7 . The method of claim 6 , wherein the harmful microorganisms are phytopathogenic harmful fungi.

8 . A method to treat a transgenic plant, comprising applying the active compound combination of claim 1 to the plant.

9 . A method to treat seed, comprising applying the active compound combination of claim 1 to the seed.

10 . A seed coated with the active compound combination of claim 1 .

11 . The composition of claim 5 , wherein the harmful microorganisms are phytopathogenic harmful fungi.

12 . The method of claim 9 , wherein the seed is seed of a transgenic plant.

13 . The active compound combination according to claim 1 , wherein the at least one compound is (I-339) (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2023
From: KLÜKEN, AGOSTINOS MICHAEL
To: BAYER AKTIENGESELLSCHAFT
Reel/Frame 063356/0863 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2023
From: MILLET, ANTHONY; NICOLAS, LIONEL; TSUCHIYA, TOMOKI; GEIST, JULIE; MONTAGNE, CYRIL
To: BAYER SAS
Reel/Frame 063356/0917 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2023
From: BAYER SAS
To: BAYER AKTIENGESELLSCHAFT
Reel/Frame 063356/0968 →
Priority Claims (1)
EP 20180707 · Jun 18, 2020 · regional
Continuity (1)
Related Publication 20240016152A1 · Jan 18, 2024
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