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CN-121985880-A - Fungicidal mixtures comprising substituted pyridines

CN121985880ACN 121985880 ACN121985880 ACN 121985880ACN-121985880-A

Abstract

Fungicidal mixtures containing substituted pyridines the present invention relates to fungicidal mixtures comprising at least one substituted pyridine (compound I) and at least one active compound II in a weight ratio of 15:1 to 1:15.

Inventors

  • P. G.W. Zeberger
  • W. Gramenos
  • N. Riddig
  • BRAHM LUTZ
  • B. J. melgett
  • A. Selmani

Assignees

  • 巴斯夫欧洲公司

Dates

Publication Date
20260505
Application Date
20240930
Priority Date
20231009

Claims (15)

  1. 1. A fungicidal mixture, which comprises a substrate and a substrate, which comprises as active ingredients the following: 1) At least one active compound of the formula I, or an N-oxide thereof, or an agriculturally useful salt, Wherein the method comprises the steps of R 1 is CHF 2 , CN R 2 is selected from CN、CH 3 、CH(CH 3 ) 2 、CH 2 CHCl 2 、CH 2 CH=CH 2 、CH 2 C(=CH 2 )CH 3 、CH 2 CCH; X 1 is selected from H, br, F, CH 3 , CCH; X 2 is selected from H, F, cl, CH 3 、CH 2 CH 3 、OCH 3 、CH 2 OCH 3 、OCHF 2 and cyclopropyl; And as component 1) the following: 2) At least one active compound II selected from the group consisting of: -a respiratory inhibitor: azoxystrobin, pyraclostrobin, tetrazole-one picolinamide, picolinamide; boscalid, fluxapyroxad Isothiazolin, fluxapyroxad hydroxylamine, fluxapyroxad, and the like iprovalicarb, and fluxapyroxad hydroxylamine; -sterol biosynthesis inhibitors (SBI fungicides) difenoconazole, prothioconazole, penconazole, 2- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -2-hydroxy-3- (1, 2, 4-triazol-1-yl) propionic acid methyl ester, methyl 2- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -2-hydroxy-3- (1, 2, 4-triazol-1-yl) propionic acid; Nucleic acid synthesis inhibitor i.e. iprovalicarb; Amino acid and protein synthesis inhibitors pyrimethanil; -signal transduction inhibitors fludioxonil; inhibitors with multi-site action, sulfur, dithianon, cu; -cell wall synthesis inhibitor tricyclazole; -plant defense inducers isotiadinil, prohexadione-calcium, phosphorous acid and salts thereof; unknown mode of action, dichlofenamate, trifluoracetam, iso Ding Yiyang quinoline, trifluoracetam; an insecticidal compound of unknown or uncertain mode of action, fluopyram; the weight ratio of these components is 1:15 to 15:1.
  2. 2. The mixture according to claim 1, wherein the component 1) is selected from the group consisting of: 1-allyl-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -7, 8-difluoro-2, 2-dimethyl-1, 2-dihydroquinazoline I-2:4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -1,2,2,7,8-pentamethyl-1, 2-dihydroquinazoline I-3:4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -7, 8-difluoro-2, 2-dimethyl-1- (prop-2-yn-1-yl) -1, 2-dihydroquinazoline 1-Allyl-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-7-methoxy-2, 2-dimethyl-1, 2-dihydroquinazoline 8-Chloro-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -7-fluoro-1, 2-trimethyl-1, 2-dihydroquinazoline I-6:7-chloro-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -1,2,2,8-tetramethyl-1, 2-dihydroquinazoline I-7:4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -7-fluoro-1,2,2,8-tetramethyl-1, 2-dihydroquinazoline I-8:7- (difluoromethoxy) -4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-1, 2-trimethyl-1, 2-dihydroquinazoline I-9:4- (5, 6-dimethylpyridin-3-yl) -2, 2-dimethyl-1- (2-methylallyl) -1, 2-dihydroquinazoline I-10:4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1- (2-methallyl) -1, 2-dihydroquinazoline 8-Fluoro-4- (4-fluoro-5, 6-dimethylpyridin-3-yl) -1, 2-trimethyl-1, 2-dihydroquinazoline I-12:4- (5, 6-dimethylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1- (2-methylallyl) -1, 2-dihydroquinazoline 1-Allyl-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -2, 2-dimethyl-1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-7-methoxy-1, 2-trimethyl-1, 2-dihydroquinazoline 7-Cyclopropyl-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-1, 2-trimethyl-1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -7-ethyl-8-fluoro-1, 2-trimethyl-1, 2-dihydroquinazoline 1-Allyl-4- (5, 6-dimethylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1, 2-dihydroquinazoline I-18:4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-7- (methoxymethyl) -1, 2-trimethyl-1, 2-dihydroquinazoline 8-Bromo-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -1, 2-trimethyl-1, 2-dihydroquinazoline 1- (2, 2-Dichlorophenyl) -4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -8-ethynyl-1, 2-trimethyl-1, 2-dihydroquinazoline I-22:4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -7, 8-difluoro-1, 2-trimethyl-1, 2-dihydroquinazoline 1-Allyl-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1, 2-dihydroquinazoline I-24:7-chloro-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-1, 2-trimethyl-1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-1, 2-dimethyl-2-phenyl-1, 2-dihydroquinazoline I-26 4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-1,2,2,7-tetramethyl-1, 2-dihydroquinazoline I-27:4- (5, 6-dimethylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1- (prop-2-yn-1-yl) -1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1- (prop-2-yn-1-yl) -1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-1, 2-trimethyl-1, 2-dihydroquinazoline 1-30:5- (7, 8-Difluoro-2, 2-dimethyl-1- (prop-2-yn-1-yl) -1, 2-dihydroquinazolin-4-yl) -3-methylpyridinecarbonitrile I-31:5- (7, 8-difluoro-1, 2-trimethyl-1, 2-dihydroquinazolin-4-yl) -3-methylpyridine carbonitrile I-32:7- (difluoromethoxy) -4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1- (prop-2-yn-1-yl) -1, 2-dihydroquinazoline 1-Allyl-7- (difluoromethoxy) -4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -8-fluoro-2, 2-dimethyl-1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -7-methoxy-1,2,2,8-tetramethyl-1, 2-dihydroquinazoline I-35:5- (7-methoxy-1,2,2,8-tetramethyl-1, 2-dihydroquinazolin-4-yl) -3-methylpyridinecarbonitrile 1-Allyl-4- (6- (difluoromethyl) -5-methylpyridin-3-yl) -7-methoxy-2,2,8-trimethyl-1, 2-dihydroquinazoline 4- (6- (Difluoromethyl) -5-methylpyridin-3-yl) -7-methoxy-2,2,8-trimethyl-1- (prop-2-yn-1-yl) -1, 2-dihydroquinazoline.
  3. 3. The mixture according to any one of claims 1 or 2, comprising compound I and compound II in a weight ratio of 1:4 to 4:1.
  4. 4. A mixture according to any one of claims 1 to 3, wherein the component 2) is at least one active compound II selected from the group consisting of: Respiratory inhibitor I: azoxystrobin, pyraclostrobin, tetrazolidone, boscalid, fluxapyroxad, and other drugs Isothiazolin, fluxapyroxad hydroxylamine, fluxapyroxad, and the like Influpyraclostrobin, penflufen and fluazinam; -sterol biosynthesis inhibitors (SBI fungicides) difenoconazole, prothioconazole and penconazole; Amino acid and protein synthesis inhibitors pyrimethanil; -signal transduction inhibitors fludioxonil; inhibitors with multi-site action, sulfur, dithianon, cu; -cell wall synthesis inhibitor tricyclazole; -plant defense inducer prohexadione-calcium; unknown mode of action, dichlorobacteria thiazide, isoquinoline Ding Yiyang quinoline and triflumizole.
  5. 5. The mixture according to any one of claims 1 to 4, wherein the component 2) is at least one active compound II selected from the group consisting of: -a respiratory inhibitor: pyraclostrobin, pyraclostrobin tetrazolium mycolone tetrazolium bacteria ketone(s); -sterol biosynthesis inhibitor (SBI fungicide) penconazole; Amino acid and protein synthesis inhibitors pyrimethanil; inhibitors with multi-site action, sulfur, dithianon, cu; unknown mode of action, triflumizole.
  6. 6. An agrochemical composition comprising a solvent or solid carrier and a composition according to any one of claims 1 to 5.
  7. 7. Use of a mixture as defined in any one of claims 1 to 6 or of an agrochemical composition as defined in claim 6 for controlling phytopathogenic harmful fungi.
  8. 8. The use according to claim 7 for combating gray mold and white mold.
  9. 9. The use according to claim 7 for combating rice leaf, neck, head and ear blast.
  10. 10. The use according to claim 7 for combating pome and stone fruit diseases.
  11. 11. Use according to claim 7 for combating leaf spot in soybeans or vegetables.
  12. 12. The use according to claim 7 for combating rhizoctonia disease (rhizoctonia solani) in several crops such as turf grass, cereal and potato and leaf vegetables.
  13. 13. The use according to claim 7 for combating stored complex infestation diseases in pomes and stone fruits.
  14. 14. The use according to claim 7 for combating different soil and seed borne pathogens.
  15. 15. A method for controlling phytopathogenic harmful fungi, which method comprises treating the fungi, their habitat or the seeds, the soil or the plants to be protected from fungal attack with an effective amount of a compound I and a compound II as defined in any of claims 1 to 5 and a compound III or a composition as defined in claim 6.

Description

Fungicidal mixtures comprising substituted pyridines The invention relates to a fungicidal mixture comprising as active components: 1) At least one active compound of the formula I, or an N-oxide thereof, or an agriculturally useful salt, Wherein the method comprises the steps of R 1 is CHF 2, CN R 2 is selected from CN、CH3、CH(CH3)2、CH2CHCl2、CH2CH=CH2、CH2C(=CH2)CH3、CH2CCH; X 1 is selected from H, br, F, CH 3, CCH; X 2 is selected from H, F, cl, CH 3、CH2CH3、OCH3、CH2OCH3、OCHF2 and cyclopropyl; And as component 1) the following: 2) At least one active compound II selected from the group consisting of: -a respiratory inhibitor: azoxystrobin, pyraclostrobin, tetrazole-one picolinamide, picolinamide (a.2.6 ic); boscalid, fluxapyroxad Isothiazolin, fluxapyroxad hydroxylamine, fluxapyroxad, and the like iprovalicarb, and fluxapyroxad hydroxylamine; -sterol biosynthesis inhibitors (SBI fungicides) difenoconazole, prothioconazole, penconazole, 2- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -2-hydroxy-3- (1, 2, 4-triazol-1-yl) propionic acid methyl ester, methyl 2- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -2-hydroxy-3- (1, 2, 4-triazol-1-yl) propionic acid; Nucleic acid synthesis inhibitor i.e. iprovalicarb; Amino acid and protein synthesis inhibitors pyrimethanil; -signal transduction inhibitors fludioxonil; inhibitors with multi-site action, sulfur, dithianon, cu; -cell wall synthesis inhibitor tricyclazole; -plant defense inducers isotiadinil, prohexadione-calcium, phosphorous acid and salts thereof; Unknown mode of action, dichlofenamate, trifluoracetone, isoquinoline Ding Yiyang (tebufloquin), trifluoracezole; an insecticidal compound of unknown or uncertain mode of action, fluopyram; the weight ratio of these components is 1:15 to 15:1. The invention also relates to the use of the mixtures and to a method for controlling phytopathogenic harmful fungi using the mixtures. Practical agricultural experience has shown that repeated and mere application of the individual active compounds in controlling harmful fungi leads in many cases to a rapid selection of those fungal strains which give rise to natural or adaptive resistance to the active compound in question. These fungi can then no longer be effectively controlled with the active compounds in question. In order to reduce the risk of selection of resistant fungal strains, mixtures of different active compounds are routinely used for controlling harmful fungi. By combining active compounds having different mechanisms of action, successful control can be ensured for a relatively long period of time. The object of the present invention is to provide compositions which, from the standpoint of effective resistance management and effective control of phytopathogenic harmful fungi, have an improved activity against harmful fungi at a reduced total amount of applied active compounds (synergistic mixture) and a broadened activity spectrum, in particular for certain indications, at an application rate as low as possible. We have found that this object is achieved by the compositions defined herein, which comprise at least one compound I and at least one compound II. Furthermore, we have found that the simultaneous (i.e. combined or separate) application of compound I and compound II or the sequential application of compound I and compound II allows better control of harmful fungi than is possible with only the compounds alone (synergistic mixtures). Compound I and/or compound II may exist in different crystal modifications (which may differ in terms of biological activity). The term "compound I" refers to a compound having the formula I. In the definitions of the variables given above, collective terms are used that generally represent the substituents in question. The term "C n-Cm" indicates the number of possible carbon atoms in each case in the substituent or substituent moiety in question. The scope of the present invention includes mixtures of the (R) -and (S) -isomers as well as racemates of compounds I and/or II and/or III having one or more chiral centers. As a result of the blocked rotation of the asymmetric substituents, atropisomers of the active compounds I and/or II and/or III may be present. They also form part of the subject matter of the invention. Compounds I and their preparation and their use as fungicidally active compounds have been described in WO 2023/01958. For example, the formation of compound I from a compound having formula 2 is suitably carried out by alkylation or acylation in the presence of a base such as a lower alkoxide or hydride of potassium or sodium. Di-lower alkyl sulfates may also be used to effect the alkylation or acylation as described in US 3,625,959. The cyclic compound having formula 2 may be prepared from ketoamine compound 1 by reaction with acetone (1 a) in the presence of ammonium acetate. In some cases, the presence of an acid such as p-toluenesulfonic acid (p-TsOH), pyridinium p-toluenesulfonate, sulfuric acid or acetic acid