Use of strobilurin-type compounds for combating phytopathogenic fungi containing amino acid substituted F129L in mitochondrial cytochrome b protein that confer resistance to Qo inhibitor XVI

Abstract

The present invention relates to strobilurin-type compounds of formula I and N-oxides and salts thereof and their use for combating plant pathogenic fungi containing an amino acid substituted F129L in the mitochondrial cytochrome b protein (also referred to as the F129L mutation in the mitochondrial cytochrome b gene) that confers resistance to Qo inhibitors, and to a method for combating such fungi. The invention also relates to processes for preparing these compounds, to compositions comprising at least one such compound, and to seeds coated with at least one such compound.

Description

[0001] illustrate

[0002] This invention relates to the use of strobilurin-type compounds of formula I, and their N-oxides and salts, for combating plant pathogenic fungi containing an amino acid substitution F129L in the mitochondrial cytochrome b protein that confers resistance to the Qo inhibitor (QoI) (also known as an F129L mutation in the mitochondrial cytochrome b gene), and to methods for combating such fungi. The invention also relates to novel compounds, methods for preparing these compounds, compositions comprising at least one such compound, plant health applications, and seeds coated with at least one such compound. Furthermore, the invention relates to a method for controlling plant pathogenic fungi with an amino acid substitution F129L in the mitochondrial cytochrome b protein, such as soybean rust fungus (Phakopsora pachyrhizi).

[0003] As used herein, “Qo inhibitors” include any substance capable of reducing and / or inhibiting respiration by binding to the ubiquinone oxidation center of the cytochrome bc1 complex in mitochondria. The oxidation center is typically located on the outer side of the inner mitochondrial membrane. Many of these compounds are also referred to as phacoemulsin-type or phacoemulsin analogs.

[0004] The mutation F129L in the mitochondrial cytochrome b (CYTB) gene should refer to any substitution of the nucleotide at codon 129 (phenylalanine; e.g., TTT or TTC) encoding "F", resulting in a substitution at the codon encoding "L" (leucine; e.g., TTA, TTG, TTG, CTT, CTC, CTA, or CTG). For example, replacing the first nucleotide 'T' at codon 129 in the CYTB (cytochrome b) gene with 'C' (TTT to CTT) would result in a single amino acid substitution from F to L at position 129 in the cytochrome b protein. Such an F129L mutation is known to confer resistance to Qo inhibitors.

[0005] Therefore, new methods are needed to control pathogen-induced diseases in crops, including those affected by pathogens containing F129L amino acid substitutions in mitochondrial cytochrome b proteins that confer resistance to Qo inhibitors. Furthermore, in many cases, particularly at low application rates, the fungicidal activity of known fungicidal agaric compounds is unsatisfactory, especially in cases where a high proportion of fungal pathogens contain mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors. Moreover, there is a continued need for new fungicidal compounds that are more effective, less toxic to mammals, less toxic to non-target organisms (such as birds, aquatic vertebrates and invertebrates, pollinators, and arthropods), and / or otherwise safer to the environment. Based on this, another object of the present invention is to provide compounds with improved activity against plant pathogenic fungi and / or a broader activity spectrum and / or even further reduced toxicity to non-target organisms (such as vertebrates and invertebrates). In many countries, certain perfluorinated and polyfluoroalkyl substances (PFAS) are receiving increasing regulatory attention due to their potential toxicity and environmental persistence. PFAS were recently redefined (OECD 2021, Reconciling Terminology of the Universe of Per- and Polyfluoroalkyl Substances: Recommendations and Practical Guidance, OECD Series on Risk Management, No. 61, OECD Publishing, Paris: https: / / www.oecd.org / chemicalsafety / portal-perfluorinated-chemicals / terminology-per-and-polyfluoroalkyl-substances.pdf; Environ. Sci. Technol. 2021 55 (23), 15575-15578: https: / / pubs.acs.org / doi / 10.1021 / acs.est.1c06896 is any chemical containing at least one fully fluorinated methyl or methylene carbon atom (without any H / Cl / Br / I atoms attached to it), that is, with a few noted exceptions, having at least one perfluorinated methyl (-CF3) or perfluorinated methylene (-CF2-).Therefore, another object of the present invention is to provide compounds that have improved activity and / or a broader activity spectrum against plant pathogenic fungi, and these compounds have low or no PFAS limitation and / or reduced environmental persistence.

[0006] Certain compounds of Formula I with phloretin type have been described in EP 370629 and WO 1998 / 23156. However, no mention is made of these compounds inhibiting fungal pathogens containing F129L substitutions in mitochondrial cytochrome b proteins that confer resistance to Qo inhibitors.

[0007] Further cytotoxic umbellatus compounds and their use against plant pathogenic fungi containing F129L amino acid substitutions in mitochondrial cytochrome b protein, which confer resistance to Qo inhibitors, are disclosed in WO 2021 / 153754, WO 2021 / 219386, WO 2021 / 219387, WO 2021 / 219388, WO 2021 / 219390 and WO 2021 / 249928.

[0008] The difference between the agaricone analogues of the present invention and those described above is particularly the specific combination of specific substitutions of a methoxymethyl group and a benzene ring attached to a side chain.

[0009] Therefore, this invention relates to compounds of formula I.

[0010]

[0011] in,

[0012] R 1 Selected from O and NH;

[0013] R 2 Selected from CH and N;

[0014] R a4 Selected from halogens, methyl groups, and methoxy groups;

[0015] R a Selected from halogens, methyl groups, and methoxy groups;

[0016] n is an integer selected from 1 and 2;

[0017] And its stereoisomers and tautomers, as well as its N-oxides and agriculturally acceptable salts.

[0018] These compounds according to the invention exhibit improved activity and / or a broader spectrum of activity against plant pathogenic fungi, and / or less toxicity to mammals, and / or less toxicity to non-target organisms such as birds, aquatic vertebrates and invertebrates, pollinating insects, and arthropods; and / or are otherwise more environmentally safe, including with low or no PFAS restrictions.

[0019] Although the invention will be described with reference to specific embodiments, this description should not be construed as limiting.

[0020] Before describing exemplary embodiments of the invention in detail, definitions important for understanding the invention are given. As used in this specification and the appended claims, unless the context clearly indicates otherwise, the singular form “a / an” also includes the corresponding plural. In the context of the invention, the terms “about” and “approximately” indicate a range of accuracy of the technical effect of the features discussed, as will be understood by those skilled in the art. This term typically indicates a deviation from the indicated value of ±20%, preferably ±15%, more preferably ±10%, and even more preferably ±5%. It should be understood that the term “comprising” is not limiting. For the purposes of the invention, the term “consisting of” is considered a preferred embodiment of the term “made up of”.

[0021] Unless otherwise stated, the following definitions are set forth to illustrate and define the meaning and scope of various terms used to describe the invention herein and the appended claims. These definitions should not be interpreted literally, as they are not intended to be general definitions and are relevant only to this application.

[0022] The term "compound I" refers to the compound of formula I. Similarly, this term applies to all sub-formulas, for example, "compound I.2" refers to the compound of formula I.2, or "compound V" refers to the compound of formula V, and so on.

[0023] When used in the context of substituents in the selection of variables, the term "independently" means that when more than one substituent is selected from many possible substituents, those substituents can be the same or different.

[0024] The organic parts or groups mentioned in the definition of variables above are a collective term for a separate list of individual group members. The term "C" v -C w "Indicates the number of carbon atoms that are possible in each case."

[0025] The term "halogen" refers to fluorine, chlorine, bromine, and iodine.

[0026] As used herein, “compound”, especially “compound I”, includes all stereoisomers and tautomers and mixtures of all ratios thereof, prodrugs, isotopic forms, agriculturally acceptable salts thereof, and their N-oxides and S-oxides.

[0027] The term "stereoisomer" is a general term used for all isomers of a single compound that differ only in the spatial orientation of their atoms. Stereoisomers include mirror-image isomers (enantiomers), mixtures of mirror-image isomers (racemic mixtures), geometric (cis / trans or E / Z) isomers (e.g., formulas Ia, Ib, and Ic and their sub-formulas), and isomers of compounds having more than one chiral center that is not a mirror image of the other (diastereomers). The term "tautomer" refers to the coexistence of two (or more) compounds that differ from each other only in the position and electron distribution of one (or more) mobile atoms, e.g., keto-enol tautomers. As used herein, the term "agriculturally acceptable salt" includes salts of active compounds prepared with acids or bases, depending on the specific substituents seen on the compounds described herein. "N-oxide" refers to an oxide containing a nitrogen atom of a nitrogen-containing heteroaryl or heterocyclic ring. N-oxides can be formed in the presence of oxidizing agents (e.g., peroxides such as m-chloroperbenzoic acid or hydrogen peroxide). N-oxides refer to amine oxides, also known as amine-N-oxides, and are compounds containing N→O bonds.

[0028] In terms of variables, the examples of intermediates correspond to the examples of compound I.

[0029] Compounds of formula I are preferred, and where applicable, compounds of all the subformulas provided herein (e.g., formulas I.1 and I.2) are also preferred. Stereoisomers of formula I, described as formulas Ia, Ib, and Ic and their corresponding subformulas (e.g., formula Ib.1), are preferred. Intermediates such as compounds II, III, IV, and V, wherein the substituents and variables (e.g., n, R) are preferred. 1 R 2 R 3 , R, R A R B R a and R b The meaning of "independently or more preferably in combination" (as defined herein as any possible combination of two or more substituents) is as follows:

[0030] Also preferred are uses, methods, mixtures, and compositions, wherein the definitions (such as plant pathogenic fungi, treatment, crop, compound II, additional active ingredient, solvent, solid carrier) have the following meanings independently or more preferably in combination, and even more preferably in combination with the preferred meanings of compound I herein (such as any possible combination of two or more definitions provided herein):

[0031] One embodiment of the present invention relates to compound I, wherein R 1 Selected from O and NH; and R 2 Selected from CH and N, provided that R 1 In the case of NH, R 2 It is N. More preferably, R 1 It's NH. Specifically, R. 1 It is NH and R 2 It is N. Another embodiment involves compound I, wherein R 1 It is O and R 2 It is CH.

[0032] According to another embodiment, R a4 Preferably selected from halogens and methoxy groups, even more preferably selected from halogens, especially F or Cl.

[0033] According to another embodiment, R a4 It is Cl.

[0034] According to another embodiment, R a4 It is F.

[0035] According to another embodiment, R a4 It is a methoxy group.

[0036] According to another embodiment, n is 1 and R a Preferably selected from halogens and methoxy groups, even more preferably selected from halogens, especially F or Cl.

[0037] According to another embodiment, n is 1 and R a It is F.

[0038] According to another embodiment, n is 1 and R a It is Cl.

[0039] According to another embodiment, n is 1 and R a In adjacent binding (2-R) a ).

[0040] According to another embodiment, n is 1 and R a It is Cl and binds at the ortho position (2-R) a ).

[0041] According to another embodiment, n is 1 and R a It is F and associated with (2-R) a ).

[0042] According to another embodiment, n is 1 and R a In meta-conjugation (3-R) a ).

[0043] According to another embodiment, n is 1 and R a It is F and it binds in the metaposition (3-R) a ).

[0044] According to another embodiment, n is 2 and two R a They are selected independently of halogens and methoxy groups, or even more preferably halogens, and particularly F or Cl.

[0045] According to another embodiment, n is 2 and two R a All are F.

[0046] According to another embodiment, n is 2 and two R a All are F.

[0047] According to another embodiment, n is 2 and an R a In adjacent combination and another R a Inter-lateral synapses (2,3-R) a 2) and two R a The components are independently selected from halogens and methoxy groups, even more preferably from halogens, and even more preferably from F or Cl (2,3-F2; 2,3-Cl2; 2-F-3-Cl; 2-Cl-3-F), and particularly the two Rs. a Both are F(2,3-F2).

[0048] According to another embodiment, n is 2 and an R a In adjacent combination and another R a Inter-conjugate on the other side (2,5-R) a 2) and two R a The components are independently selected from halogens and methoxy groups, even more preferably from halogens, and even more preferably from F or Cl (2,5-F2; 2,5-Cl2; 2-F-5-Cl; 2-Cl-5-F), particularly the two R groups. a Both are F(2,5-F2).

[0049] According to another embodiment, n is 2 and two R a In adjacent binding (2,6-R) a2) and are independently selected from halogens and methoxy groups, even more preferably from halogens, particularly from F or Cl. According to another embodiment, n is 2 and the two Rs... a Both are F and they bind in adjacent positions (2,6-F2).

[0050] According to another embodiment, n is 2 and two R a In meta-binding (3,5-R) a 2) and are independently selected from halogens and methoxy groups, even more preferably from halogens, particularly from F or Cl (3,5-F2; 3,5-Cl2; 3-F-5-Cl; 3-Cl-5-F). According to another embodiment, n is 2 and the two Rs... a Both are F and are interpositional (3,5-F2).

[0051] According to another embodiment, n is 1, R a It is Cl and R a4 It is F.

[0052] According to another embodiment, n is 1, R a It is Cl and R a4 It is Cl.

[0053] According to another embodiment, n is 1, R a It is F and R a4 It is F.

[0054] According to another embodiment, n is 1, R a It is F and R a4 It is a methoxy group.

[0055] According to another embodiment, n is 1, R a It is 2-Cl and R a4 It is F.

[0056] According to another embodiment, n is 1, R a It is 2-Cl and R a4 It is Cl.

[0057] According to another embodiment, n is 1, R a It is 2-F and R a4 It is F.

[0058] According to another embodiment, n is 1, R a It is 2-F and R a4 It is a methoxy group.

[0059] According to another embodiment, n is 1, R a It is 3-Cl and R a4 It is F.

[0060] According to another embodiment, n is 1, R a It is 3-Cl and R a4 It is Cl.

[0061] According to another embodiment, n is 1, R a It is 3-F and R a4 It is F.

[0062] According to another embodiment, n is 1, R a It is 3-F and R a4 It is a methoxy group.

[0063] According to another embodiment, n is 1, R a It is 4-Cl and R a4 It is F.

[0064] According to another embodiment, n is 1, R a It is 4-Cl and R a4 It is Cl.

[0065] According to another embodiment, n is 1, R a It is 4-F and R a4 It is F.

[0066] According to another embodiment, n is 1, R a It is 4-F and R a4 It is a methoxy group.

[0067] According to another embodiment, n is 2, and two R a Both are Cl and R a4 It is Cl.

[0068] According to another embodiment, n is 2, and two R a Both are F and R a4 All are F.

[0069] According to another embodiment, n is 2, and two R a Both are F and R a4 It is a methoxy group.

[0070] According to another embodiment, n is 2, and two R a Both are Cl and R a4 It is a methoxy group.

[0071] According to another embodiment, n is 2, and two R a Both are Cl, one is adjacent and the other is R. a Meta-binding on the same side (2,3-Cl2), and R a4 It is Cl.

[0072] According to another embodiment, n is 2, and two Ra Both are F, one is adjacent and the other is R. a Inter-lateral synapses (2,3-F2) and R a4 It is F.

[0073] According to another embodiment, n is 2, and two R a Both are F, one is adjacent and the other is R. a Inter-lateral synapses (2,3-F2) and R a4 It is a methoxy group.

[0074] According to another embodiment, n is 2, and two R a Both are Cl, one is adjacent and the other is R. a Meta-binding on the same side (2,3-Cl2), and R a4 It is a methoxy group.

[0075] According to another embodiment, n is 2, and two R a Both are Cl, one is adjacent and the other is R. a Meta-binding (2,5-Cl2) on the other side, and R a4 It is Cl.

[0076] According to another embodiment, n is 2, and two R a Both are F, one is adjacent and the other is R. a On the other side, there was a meta-conjugation (2,5-F2), and R a4 It is F.

[0077] According to another embodiment, n is 2, and two R a Both are F, one is adjacent and the other is R. a On the other side, there was a meta-conjugation (2,5-F2), and R a4 It is a methoxy group.

[0078] According to another embodiment, n is 2, and two R a Both are Cl, one is adjacent and the other is R. a Meta-binding (2,5-Cl2) on the other side, and R a4 It is a methoxy group.

[0079] According to another embodiment, n is 2, and two R a Both are Cl, both are ortho-binding (2,6-Cl2), and R a4 It is Cl.

[0080] According to another embodiment, n is 2, and two R aBoth are F, both are adjacent associative (2,6-F2), and R a4 It is F.

[0081] According to another embodiment, n is 2, and two R a Both are F, both are adjacent associative (2,6-F2), and R a4 It is a methoxy group.

[0082] According to another embodiment, n is 2, and two R a Both are Cl, both are ortho-binding (2,6-Cl2), and R a4 It is a methoxy group.

[0083] According to another embodiment, n is 2, and two R a Both are Cl, both are meta-bound (3,5-Cl2), and R a4 It is Cl.

[0084] According to another embodiment, n is 2, and two R a All are F, all are meta-cohesive (3,5-F2), and R a4 It is F.

[0085] According to another embodiment, n is 2, and two R a All are F, all are meta-cohesive (3,5-F2), and R a4 It is a methoxy group.

[0086] According to another embodiment, n is 2, and two R a Both are Cl, both are meta-bound (3,5-Cl2), and R a4 It is a methoxy group.

[0087] According to a further preferred embodiment, the present invention relates to compounds of formula I, wherein:

[0088] R 1 Selected from O and NH;

[0089] R 2 Selected from CH and N, provided that R 1 In the case of NH, R 2 It is N;

[0090] R a4 Selected from F, Cl and methoxy groups;

[0091] R a Selected from halogens;

[0092] n is an integer selected from 1 and 2;

[0093] And its stereoisomers and tautomers, as well as its N-oxides and agriculturally acceptable salts.

[0094] According to a further preferred embodiment, the present invention relates to compounds of formula I, wherein:

[0095] R 1 It is O;

[0096] R 2 It is CH;

[0097] R a4 Selected from F, Cl and methoxy groups;

[0098] R a Selected from F and Cl;

[0099] n is 2;

[0100] And its stereoisomers and tautomers, as well as its N-oxides and agriculturally acceptable salts.

[0101] According to a further preferred embodiment, the present invention relates to compounds of formula I, wherein:

[0102] R 1 It is O;

[0103] R 2 It is CH;

[0104] R a4 Selected from F, Cl and methoxy groups;

[0105] R a Selected from F and Cl;

[0106] n is an integer selected from 1 and 2;

[0107] And its stereoisomers and tautomers, as well as its N-oxides and agriculturally acceptable salts.

[0108] According to a further preferred embodiment, the present invention relates to compounds of formula I, wherein:

[0109] R 1 Selected from O and NH;

[0110] R 2 Selected from CH and N, provided that R 1 In the case of NH, R 2 It is N;

[0111] R a4 Selected from F, Cl and methoxy groups;

[0112] R a Selected from halogens;

[0113] n is 2;

[0114] And its stereoisomers and tautomers, as well as its N-oxides and agriculturally acceptable salts.

[0115] According to another embodiment, R 1 It is NH and R 2 N is present, and these compounds have formula I.1:

[0116] .

[0117] According to another embodiment, R 1 It is O and R 2 It is N, and these compounds have formula I.2:

[0118] .

[0119] According to another embodiment, R 1 It is O and R 2 These compounds are CH, and have formula I.3:

[0120] .

[0121] Preferably, the R of compound I a4 It is one of the following groups a4-1 to a4-6:

[0122]

[0123] A particularly preferred embodiment of the present invention relates to compound I, wherein R a It is one of the following groups a-1 to a-6:

[0124]

[0125] In 450 independent embodiments, compound I has the formula I.1, I.2, or I.3 as described above, R a4 and 1 or 2 R a These compounds are named IA-1 to IA-450 according to any row in Table A below:

[0126] Table A:

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] These compounds I are substituted (2E)-2-methoxyimino-2-[2-[[(Z)-(2-methoxy-1-phenyl-ethylidene)amino]oxymethyl]-3-methyl-phenyl]-N-methyl-acetamide (Formula I.1), (2E)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-phenyl)ethylidene]amino]oxymethyl]-3-methyl-phenyl]acetate (Formula I.2) and (E)-3-methoxy-2-[2-[[(Z)-[2-methoxy-1-phenyl)ethylidene]amino]oxymethyl]-3-methyl-phenyl]prop-2-enoic acid methyl ester (Formula I.3) and their stereoisomers (e.g., as depicted by Formulas Ia, Ib and Ic below).

[0136] Therefore, the present invention also relates to stereoisomers as described below: E / E isomers of formula Ia:

[0137]

[0138] Z / E isomers of formula Ib:

[0139]

[0140] Z / Z isomers of the compound Ic:

[0141] .

[0142] Therefore, the present invention also relates to R 1 It is NH and R 2 These are compounds Ia of N, which have the formula Ia.1, involving R. 1 It is O and R 2 These are compounds Ia of N, which have the formula Ia.2 and involve R. 1 It is O and R 2 These are CH compounds Ia, and these compounds have formula Ia.3:

[0143] , , .

[0144] The present invention further relates to R 1 It is NH and R 2These are compounds Ib of N, which have the formula Ib.1, involving R. 1 It is O and R 2 These are compounds Ib of N, which have the formula Ib.2 and involve R. 1 It is O and R 2 These are CH compounds Ib, and these compounds have the formula Ib.3:

[0145] , , .

[0146] The present invention further relates to R 1 It is NH and R 2 These are compounds Ic of N, which have the formula Ic.1, involving R. 1 It is O and R 2 These are compounds of N, Ic, which have the formula Ic.2, and involve R. 1 It is O and R 2 These are CH compounds Ic, and these compounds have formula Ic.3:

[0147] , , .

[0148] In 150 independent embodiments, compound I has formula Ia.1, wherein R a4 and 1 or 2 R a These compounds are named Ia.1-B-1 to Ia.1-B-150, with substituents in any row of Table B below.

[0149] In 150 independent embodiments, compound I has formula Ia.2, wherein R a4 and 1 or 2 R a These compounds are named Ia.2-B-1 to Ia.2-B-150, with substituents in any row of Table B below.

[0150] In 150 independent embodiments, compound I has formula Ia.3, wherein R a4 and 1 or 2 R a These compounds are named Ia.3-B-1 to Ia.3-B-150, with substituents in any row of Table B below.

[0151] In 150 independent embodiments, compound I has formula Ib.1, wherein R a4 and 1 or 2 R a These compounds are named Ib.1-B-1 to Ib.1-B-150, with substituents in any row of Table B below.

[0152] In 150 independent embodiments, compound I has formula Ib.2, wherein R a4 and 1 or 2 R a These compounds are named Ib.2-B-1 to Ib.2-B-150, with substituents in any row of Table B below.

[0153] In 150 independent embodiments, compound I has formula Ib.3, wherein R a4 and 1 or 2 R a These compounds are named Ib.3-B-1 to Ib.3-B-150, with substituents listed in any row of Table B below.

[0154] In 150 independent embodiments, compound I has formula Ic.1, wherein R a4 and 1 or 2 R a These compounds are named Ic.1-B-1 to Ic.1-B-150, with substituents in any row of Table B below.

[0155] In 150 independent embodiments, compound I has formula Ic.2, wherein R a4 and 1 or 2 R a These compounds are named Ic.2-B-1 to Ic.2-B-150, with substituents in any row of Table B below.

[0156] In 150 independent embodiments, compound I has formula Ic.3, wherein R a4 and 1 or 2 R a These compounds are named Ic.3-B-1 to Ic.3-B-150, with substituents in any row of Table B below.

[0157] Table B:

[0158]

[0159]

[0160]

[0161] The compounds according to the invention comprise isomers described in Formulas I, Ia, Ib, and Ic. Preferably, the compounds according to the invention comprise more than 50% of the stereoisomers described in Formula I and less than 50% of the stereoisomers described in Formulas Ia, Ib, and Ic. Preferably, the compounds according to the invention comprise more than 80% of the stereoisomers described in Formula I and less than 20% of the stereoisomers described in Formulas Ia, Ib, and Ic. Preferably, the compounds according to the invention comprise more than 90% of the stereoisomers described in Formula I and less than 10% of the stereoisomers described in Formulas Ia, Ib, and Ic. Preferably, the compounds according to the invention comprise more than 95% of the stereoisomers described in Formula I and less than 5% of the stereoisomers described in Formulas Ia, Ib, and Ic. Preferably, the compounds according to the invention comprise more than 98% of the stereoisomers described in Formula I and less than 2% of the stereoisomers described in Formulas Ia, Ib, and Ic. Preferably, the compound according to the invention comprises more than 99% of the stereoisomers described in Formula I and less than 1% of the stereoisomers described in Formulas Ia, Ib and Ic. Preferably, the compound according to the invention comprises more than 99.5% of the stereoisomers described in Formula I and less than 0.5% of the stereoisomers described in Formulas Ia, Ib and Ic.

[0162] According to another embodiment, the compound according to the invention comprises stereoisomers depicted in Formula I and Formula Ia. Preferably, the compound according to the invention comprises more than 50% of the stereoisomers depicted in Formula I and less than 50% of the stereoisomers depicted in Formula Ia. Preferably, the compound according to the invention comprises more than 80% of the stereoisomers depicted in Formula I and less than 20% of the stereoisomers depicted in Formula Ia. Preferably, the compound according to the invention comprises more than 90% of the stereoisomers depicted in Formula I and less than 10% of the stereoisomers depicted in Formula Ia. Preferably, the compound according to the invention comprises more than 95% of the stereoisomers depicted in Formula I and less than 5% of the stereoisomers depicted in Formula Ia. Preferably, the compound according to the invention comprises more than 99% of the stereoisomers depicted in Formula I and less than 1% of the stereoisomers depicted in Formula Ia. Preferably, the compound according to the invention comprises more than 99.5% of the stereoisomers depicted in Formula I and less than 0.5% of the stereoisomers depicted in Formula Ia. According to another embodiment, the compound according to the invention is essentially a stereoisomer as described in Formula I, which is a stereoisomer of pure stereoisomer.

[0163] synthesis

[0164] The compounds can be obtained by various routes similar to known prior art methods (e.g., EP 463488, WO 2021 / 153754, WO 2021 / 219386, WO 2021 / 219387, WO 2021 / 219388, WO 2021 / 219390 and WO 2021 / 249928), and advantageously as shown in schemes 1 to 4 and the following examples section. Option 1 The text describes a suitable method:

[0165]

[0166] It begins with the conversion of the ketone to the corresponding oxime using hydroxylamine hydrochloride and a base such as pyridine, NaOH, or sodium acetate (NaAc) in a polar solvent such as methanol, a methanol-water mixture, or ethanol at a temperature of 60°C to 100°C, preferably about 65°C. In the case of an E / Z mixture, the isomers can be separated by known purification techniques (e.g., column chromatography, crystallization, distillation, etc.). Then, under alkaline conditions using, for example, sodium hydride, cesium carbonate, or potassium carbonate as a base and using an organic solvent such as dimethylformamide (DMF) or acetonitrile (AcN), preferably cesium carbonate as a base and AcN as a solvent, coupling with intermediate IV at room temperature (RT) of about 24°C is carried out, where X is a leaving group, such as a halogen, toluenesulfonate, or methanesulfonate group, preferably X is Cl or Br. Ester compound I (wherein R...) 1 (R) can be converted into an amide of formula I (where R is O) by reacting it with methylamine (preferably a 40% aqueous solution) at RT using tetrahydrofuran (THF) as a solvent. 1(It is NH). In the case of obtaining an E / Z mixture, the isomers can be separated by known purification techniques (e.g., column chromatography, crystallization, distillation, etc.). Therefore, in addition to E / Z isomers (e.g., (2E)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-(2,4,6-trifluorophenyl)ethylene]amino]oxymethyl]-3-methyl-phenyl]-N-methyl-acetamide), these procedures can also be used to provide the corresponding E / E, Z / E, and Z / Z isomers of formulas Ia, Ib, and Ic (e.g., (2E)-2-methoxyimino-2-[2-[[(E)-[2-methoxy-1-(2,4,6-difluorophenyl)ethylene]amino]oxymethyl]-3-methyl-phenyl]-N-methyl-acetamide). [2Z]-2-methoxyimino-2-[2-[[(E)-[2-methoxy-1-(2,4-difluorophenyl)ethylene]amino]oxymethyl]-3-methyl-phenyl]-N-methyl-acetamide, and (2Z)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-(2,4-difluorophenyl)ethylene]amino]oxymethyl]-3-methyl-phenyl]-N-methyl-acetamide).

[0167] Another general method for preparing compound I is described in Option 2 middle:

[0168]

[0169] Intermediate IV is reacted with N-hydroxysuccinimide VI in DMF using a base such as triethylamine. The reaction temperature is typically 50°C to 70°C, preferably about 70°C. The conversion to the corresponding O-benzylhydroxyamine, intermediate VIII, is achieved by removing the phthalimide group, preferably using hydrazine hydrate in methanol as a solvent at 25°C. Alternatively, removing the phthalimide group using methylamine in methanol as a solvent at 25°C can provide intermediate IX. Intermediates VIII and IX can be condensed with a ketone, respectively, using acetic acid or pyridine in methanol as a solvent at a temperature of 50°C to 65°C. Alternatively, this condensation can also be carried out using titanium ethoxide (IV) (Ti(OEt)4) as a solvent at about 70°C. The desired product is usually accompanied by an undesirable isomer, which can be removed, for example, by column chromatography or crystallization.

[0170] A general method for preparing intermediate IV is shown in Option 3 middle:

[0171]

[0172] Compound XI can be obtained from X via lithium-halogen exchange or by generating a Grignard reagent and further reacting it with dimethyl oxalate or chloromethyl oxalate in the presence of a solvent. Preferred solvents are THF and 2-methyl-THF, and the temperature can be between -70°C and -78°C. The conversion of intermediate XI to intermediate XII can be achieved using N-methylhydroxylamine hydrochloride and a base such as pyridine or NaAc in a polar solvent such as methanol. The reaction temperature is preferably about 65°C. Typically, an E / Z mixture is obtained, and the isomers can be separated using purification techniques known in the art, such as column chromatography or crystallization. Bromination of intermediate XII provides the desired intermediate compound IV, wherein R... 1 It is O and R 2 = N. This reaction between intermediate XII and N-bromosuccinimide (NBS) is carried out in a solvent such as carbon tetrachloride, chlorobenzene, or AcN, using a free radical initiator such as 1,1'-azobis(cyclohexanecarboxynitrile) or azobisisobutyronitrile, and at a temperature of 70°C to 100°C. The preferred free radical initiator is 1,1'-azobis(cyclohexanecarboxynitrile), the preferred solvent is chlorobenzene, and the preferred temperature is 80°C.

[0173] Most ketones of general formula II are commercially available; however, for those that are not commercially available, their preparation is carried out internally using methods known in the art. Various methods for synthesizing these ketones are described in the literature. Option 4 middle:

[0174]

[0175] Ketone II can be obtained from the corresponding halogen-containing precursor XIV, wherein X is preferably bromine or iodine. Ketone II can be provided by lithium-halogen exchange in compound XIV using n-butyllithium (J Org Chem, 1998, 63 (21), 7399-7407) or by synthesizing the corresponding Grignard reagent using THF as a solvent (Nature Communications, 2017, 8(1), 1-7), followed by reaction with N-methoxy-N-methylalkoxyacetamide at about -70°C to -78°C.

[0176] Compound I and its compositions are suitable as fungicides, effective against a broad spectrum of plant pathogenic fungi, including soil-borne fungi, particularly those from the classes Plasmodiomycetes, Oomycetes, Chytrididae, Zygomycetes, Ascomycetes, Basidiomycetes, and Fungi imperfecti. They can be used in crop protection as foliar fungicides, seed dressing fungicides, and soil fungicides.

[0177] Compound I and its compositions are preferably used to control plant pathogenic fungi in the following: various cultivated plants, such as cereals, such as wheat, rye, barley, triticale, oats, or rice; beets, such as sugar beets or forage beets; fruits, such as pome (apples, pears, etc.), drupes (such as plums, peaches, apricots, cherries), or berries, also known as strawberries, raspberries, blackberries, currants, etc.; legumes, such as lentils, peas, alfalfa, or soybeans; oilseed plants, such as rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbits, such as squash, cucumbers, or melons; fiber plants, such as cotton, flax, hemp, etc. Or jute; citrus fruits, such as oranges, lemons, grapefruits, or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds, or red peppers; laurel plants, such as avocados, cinnamon, or camphor; energy and raw material plants, such as corn, soybeans, rapeseed, sugarcane, or oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapevines (table grapes and grape juice vines); hops; turf; stevia (also known as stevia); natural rubber plants; or ornamental and forest plants, such as flowers, shrubs, broad-leaved trees, or evergreen trees (conifers, eucalyptus, etc.); plant propagation materials, such as seeds; and crop materials of these plants.

[0178] More preferably, compound I and its compositions are used to control fungi in the following: field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugarcane; fruits; vines; ornamental plants; or vegetables, such as cucumbers, tomatoes, green beans, or squash.

[0179] The term "plant propagation material" should be understood to refer to all reproductive parts of a plant, such as seeds; and nutrient plant material that can be used for plant propagation, such as cuttings and tubers (e.g., potatoes). This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds, and other parts of a plant; including seedlings and young plants that are transplanted after germination or emergence.

[0180] Preferably, plant propagation material is treated with compound I and its compositions for the control of fungi in the following: cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

[0181] According to the present invention, all of the above-mentioned cultivated plants should be understood to include all species, subspecies, varieties, cultivars and / or hybrids belonging to the corresponding cultivated plants, including but not limited to winter and spring varieties, especially cereals such as wheat and barley, and rapeseed, such as winter wheat, spring wheat, winter barley, etc.

[0182] Maize, also known as Indian maize or Zea mays, includes all varieties of maize, such as feed maize and sweet maize. According to the present invention, this includes all maize or maize subspecies and / or varieties, particularly floury maize (Zea mays var. amylacea), popcorn maize (Zea mays var. everta), dent maize (Zea mays var. indentata), flint maize (Zea mays var. indurata), sweet maize (Zea mays var. saccharata and var. rugosa), waxy maize (Zea mays var. ceratina), amylomaize (amylomaize), pod maize, or wild maize (Zea mays var. tunicata). tunicata) and striped maize (maize japonica variety (Zea mays var. japonica)).

[0183] Most soybean cultivars can be classified as either indeterminate or determinate, while wild soybean (Glycine soja) (the wild ancestor of soybean) is indeterminate (PNAS [Proceedings of the National Academy of Sciences] 2010, 107 (19) 8563-8568). Indeterminate varieties (maturity group, MG 00 to MG 4.9) are characterized by continuous vegetative growth after flowering begins, while determinate soybean varieties (MG 5 to MG 8) are characterized by having completed most of their vegetative growth by the time flowering begins. According to the present invention, all soybean cultivars or varieties, particularly indeterminate and determinate varieties or varieties, are included.

[0184] The term "cultivated plant" should be understood to include plants that have been modified through mutagenesis or genetic engineering to provide new traits or modify existing traits. Mutagenesis includes random mutagenesis using X-rays or mutagenic chemicals, and also includes targeted mutagenesis to produce mutations at specific loci in the plant genome. Targeted mutagenesis often uses oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or broad-spectrum nucleases. Genetic engineering typically uses recombinant DNA technology to produce modifications in the plant genome that are not readily available in nature through hybridization, mutagenesis, or natural recombination. Typically, one or more genes are integrated into the plant genome to add or improve or modify traits. These integrated genes are also called transgenes, and plants containing such transgenes are called transgenic plants. Plant transformation processes typically produce several transformation events, which differ at the genomic loci in which the transgene has been integrated. Plants containing a specific transgene at a specific genomic locus are often described as containing a specific "event," identified by the name of that specific event. Traits that have been introduced into plants or modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought. Herbicide tolerance has been generated through mutagenesis and genetic engineering. Plants induced to tolerate acetyllactate synthase (ALS) inhibitor herbicides through mutagenesis and breeding are available, for example, under the name Clearfield®. Herbicide tolerance to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides (such as bromobenzonitrile and iodobenzonitrile), sulfonylurea herbicides, ALS inhibitors, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (like isoxaflutole and mesotrione) has been generated through transgenic technology.

[0185] Transgenic organisms providing herbicide tolerance traits include: glyphosate tolerance: cp4 epsps, epspsgrg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; glufosinate tolerance: pat and bar; 2,4-D tolerance: aad-1, aad-12; dicamba tolerance: dmo; benzyl nitrile herbicide tolerance: bxn; sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA; ALS inhibitor tolerance: csr1-2; and HPPD inhibitor tolerance: hppdPF, W336, avhppd-03.

[0186] Transgenic maize events containing herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-Ø1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275. Transgenic soybean events containing herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTØH2, W62, W98, FG72, and CV127. Transgenic cotton events containing herbicide tolerance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40. Transgenic canola events containing herbicide tolerance genes include, but are not excluded, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0187] Transgenic genes providing insect resistance are preferably toxin genes from Bacillus species and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. Alternatively, plant-derived transgenes, such as genes encoding protease inhibitors like CpTI and pinII, can be used. Another approach is to use transgenes such as dvsnf7 to produce double-stranded RNA in plants.

[0188] Transgenic maize events containing insecticidal protein genes or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098. Transgenic soybean events containing insecticidal protein genes include, but are not limited to, MON87701, MON87751, and DAS-81419. Transgenic cotton events containing insecticidal protein genes include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFMCry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0189] Cultivated plants with increased yields have been produced by using transgenic athb17 (e.g., maize event MON87403) or bbx32 (e.g., soybean event MON87712).

[0190] Cultivated plants with improved oil content have been produced using the following transgenic genes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A (e.g., soybean events 260-05, MON87705, and MON87769).

[0191] Tolerance to abiotic conditions (such as drought) has been developed through the use of transgenic cspB (maize event MON87460) and Hahb-4 (soybean event IND-ØØ41Ø-5).

[0192] Traits are typically combined by combining genes during transformation events or by combining different events during the breeding process, resulting in cultivated plants with superimposed traits. Preferred combinations of traits include combinations of herbicide tolerance traits from different groups of herbicides, combinations of insect tolerance to different insect species, particularly to Lepidoptera and Coleoptera, combinations of herbicide tolerance with resistance to one or more types of insects, combinations of herbicide tolerance with increased yield, and combinations of herbicide tolerance with tolerance to abiotic conditions.

[0193] Plants containing single or superimposed traits, as well as the genes and events that provide these traits, are well known in the field. For example, detailed information on mutagenic or integrated genes and corresponding events is available from the websites of organizations such as the International Service for the Application of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Centre for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase). Further information regarding specific events and methods for detecting these events can be found in WO 01 / 031042, WO 01 / 041558, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, and WO 13 / 003558 for canola events MS1, MS8, RF3, GT73, MON88302, and KK179; and in WO 02 / 034946, WO 03 / 036831, WO 11 / 153186, and WO 13 / 003558 for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, and 81910 ...MON531 (MON15985), MON531 (MON15985), MON531 (MON15985), MON531 (MON15985), MON531 (MON15 02 / 100163、WO 02 / 100163、WO 03 / 013224、WO 04 / 072235、WO 04 / 039986、WO 05 / 103266、WO 05 / 103266、WO 06 / 128573、WO 07 / 017186、WO 08 / 122406, WO 08 / 151780, WO 12 / 134808, WO 13 / 112527;For the corn incident, GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, and MON87419 can be found in WO 98 / 044140, US 02 / 102582, US 03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO 05 / 061720, WO 05 / 059103, and WO 06 / 098952、WO 06 / 039376、US 2007 / 292854、WO07 / 142840、WO 07 / 140256、WO 08 / 112019、WO 09 / 103049、WO 09 / 111263、WO 10 / 077816、WO11 / 084621、WO 11 / 062904、WO 11 / 022469、WO 13 / 169923、WO 14 / 116854、WO 15 / 053998, WO15 / 142571; for potato events E12, F10, J3, J55, V11, X17, Y9, see WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825; for the rice incident LLRICE06, LLRICE601, LLRICE62, see WO 00 / 026345, WO 00 / 026356, WO 00 / 026345;Furthermore, for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751, these can be found in WO 04 / 074492, WO 06 / 130436, WO06 / 108674, WO 06 / 108675, WO 08 / 054747, WO 08 / 002872, WO 09 / 064652, WO 09 / 102873, WO10 / 080829, WO10 / 037016, WO11 / 066384, WO11 / 034704, WO12 / 051199, WO12 / 082548, WO13 / 016527, WO13 / 016516, WO14 / 201235.

[0194] The application of compound I and its combinations to cultivated plants can result in effects specific to cultivated plants containing a particular transgene or event. These effects may involve alterations in growth behavior or resistance to biotic or abiotic stresses. Such effects may in particular include increased yield, increased resistance or tolerance to insect, nematode, fungus, bacteria, mycoplasma, virus, or viroid pathogens, as well as early vigor, early or delayed maturity, cold or heat tolerance, and altered amino acid or fatty acid profiles or contents.

[0195] Compound I and its combinations are particularly suitable for controlling the pathogens causing the following plant diseases:

[0196] White rust (A. candida) species on ornamental plants, vegetables (e.g., white rust fungus), and sunflowers (e.g., white rust fungus *A. tragopogonis*); *Albugo* species (white rust disease) on vegetables (e.g., *Albugo* dauci or *Albugo* porri), rapeseed (*Albugo* brassicicola or *Albugo* brassicae), sugar beets (*Albugo* tenuis), fruits (e.g., *Albugo* grandis), rice, soybeans, potatoes, and tomatoes (e.g., *Albugo* solani, *Albugo* or *Albugo* alternata), tomatoes (e.g., *Albugo* solani or *Albugo* alternata), and wheat (e.g., *Albugo* wheat). Alternaria species on *Alternaria triticina* (Alternaria leaf spot); Aphanomyces species on sugar beets and vegetables; Ascochyta species on cereals and vegetables, such as *A. tritici* on wheat (anthracnose) and *A. hordei* on barley; *Aureobasidium zeae* (synonym *Kapatiella zeae*) on maize; Bipolaris and Drechslera species (sexual form: *Cochliobolus* species), such as *D. maydis* on maize (small leaf spot) or *B. zeicola* on maize (large leaf spot), such as *B. zeicola* on cereals (root rot). Sorokiniana) and, for example, B. oryzae on rice and turfgrass; Blumeria graminis (formerly known as Erysiphe graminis) (powdery mildew) on cereals (e.g., wheat or barley); Botrytis cinerea (sexual form: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbage); Botrytis squamosa or Botrytis squamosa on onion family plants, rapeseed, ornamental plants (e.g., Beliptica), vines, forest plants, and wheat.allii); *Bremia lactucae* on lettuce (downy mildew); *Ceratocystis* species (synonym Ophiostoma) on broadleaf and evergreen trees (rot or wilting), such as *C. ulmi* on elm trees (Dutch elm disease); maize (e.g., gray leaf spot: *C. zeae-maydis*), rice, sugar beets (e.g., *C. beticola*), sugarcane, vegetables, coffee, soybeans (e.g., *C. sojina* or *C. kikuchii*) and *Cercospora* species on rice (Cercospora leaf spot); *Cladobotryum* species (synonym Dactylium) on mushrooms (e.g., *C. mycophilum* (formerly known as *Dactylium dendriticum*)). Dendroides), sexual form: Nectria albertinii, pink parasite (Nectria rosella) synonym Hypomyces rosellus; tomato (e.g. C. fulvum: leaf mold) and Cladosporium species on cereals, such as C. herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); maize (C. carbonum), cereals (e.g. C. sativus, asexual form: B. sorokiniana) and rice (e.g. C. miyabeanus, asexual form: H. rice long-spore). Species of the genus *Cochliobolus* (asexual form: *Helminthosporium* of the genus *Bipolaris*) (leaf spot); cotton (e.g. *C. gossypii*), maize (e.g. *C. graminicola*: anthracnose and stem rot), soft fruit, potato (e.g. *C. coccodes*: black spot), bean (e.g. *C. lindemuthianum*), soybean (e.g. *C. truncatum* or *C. gloeosporioides*)), vegetables (e.g. *C. lagenarium* or *C. capsici*)), and fruit (e.g. *C. oxysporum*).Anthracnose includes species of *Colletotrichum* (sexual form: *Glomerella*) on coffee (e.g., *C. coffeanum* or *C. kahawae*) and various crops (*C. gloeosporioides*). Other diseases include: species of *Corticium*, such as *C. sasakii* on rice (sheath blight); *Corynespora cassiicola* on soybeans, cotton, and ornamental plants (leaf spot); species of *Cycloconium*, such as *C. oleaginum* on olive trees; and diseases of fruit trees and vines (e.g., *C. liriodendri*, sexual form: *Neonectria liriodendri*). Foot disease) and Cylindrocarpon species on ornamental plants (e.g., fruit tree canker or young vine decay, sexual type: Nectria or Neonectria species); Dematophoranecatrix on soybean (sexual type: Rosellia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybean (damping-off); corn, cereals such as barley (e.g., D. teres, net blotch) and wheat (e.g., D. tritici-repentis, brown spot disease). *Drechslera* species (synonyms: *Helminthosporium*, sexual type: *Pyrenophora*) on rice and turfgrass; *Esca* (dieback, apoplexy) on vines, caused by *Formitiporia punctata* (synonyms: *Phellinus punctata*) and *Formitiporia punctata* (F. truncatum).Caused by *Phaeomoniella mediterranea*, *Phaeomoniella chlamydospora* (formerly *Phaeoacremonium chlamydosporum*), *Phaeoacremonium aleophilum*, and / or *Botryosphaeria obtusa*; *Elsinoe* species on pear fruit (*E. pyri*), soft fruit (*E. veneta*): anthracnose) and vines (*E. ampelina*): anthracnose; *Entyloma oryzae* on rice (leaf smut); *Epicoccum* species on wheat (black mold); sugar beet (*E. beet powdery mildew*). Powdery mildew (e.g., E. pisi) on vegetables such as gourds (e.g., E. cichoracearum), cabbage, rapeseed (e.g., E. cruciferarum); Erysiphe species (powdery mildew) on fruit trees, vines, and ornamental trees (Eutypa lata) (curved spore canker or shoot blight, asexual form: Cytosporinalata, synonym Libertella blepharis); corn (e.g., E. maize large leaf spot). Species of the genus *Exserohilum* (synonym *Helminthosporium*) on *turcicum*; species of the genus *Fusarium* (sexual form: *Gibberella*) on various plants (causing wilting, root or stem rot), such as *F. graminearum* or *F. culmorum* on cereals (e.g., wheat or barley) (causing root rot, scab, or head blight), *F. oxysporum* on tomatoes, *F. solani* (a soybean-specific form of *Fusarium*, a new synonym for soybean sudden death syndrome pathogen *F. virguliforme*) and *F. tucumaniae* and *F. brasiliense* (both causing sudden death syndrome) on soybeans, and *F. verticillata* on maize.verticillioides; Gaeumannomyces graminis (take-all) on cereals (e.g., wheat or barley) and maize; Gibberella species on cereals (e.g., G. zeae) and rice (e.g., G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pears and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium species on Rosaceae and juniper, such as G. brown glomerulosa on pears. sabinae (rust); Helminthosporium species (synonyms: Drechslera, sexual form: Cochliobolus) on corn, cereals, potatoes, and rice; Hemileia species, such as H. vastatrix on coffee (coffee leaf rust); Isariopsis clavispora (synonyms: Cladosporium vitis) on vines; Macropomina phaseolina (synonyms: Macropomina phaseoli) on soybeans and cotton (root and stem rot); Microdochium (synonyms: Fusarium) on cereals (e.g., wheat or barley) (powdery mildew); Microsphaera on soybeans. (Powdery mildew); Monilinia species on drupes and other Rosaceae plants, such as *M. laxa*, *M. fructicola*, and *M. fructigena* (synonyms: *Monilia* species: flower rot and branch blight, brown rot); Mycosphaerella species on cereals, bananas, soft fruits, and peanuts, such as *M. gracilis* on wheat.*Zymoseptoria tritici* (asexual form: *Zymoseptoria tritici*, formerly known as *Septoria tritici*: *Zymoseptoria tritici* leaf spot), or *M. fijiensis* (synonym *Pseudocercospora fijiensis*: black Sigatoka disease) and *M. musicola* on bananas, *M. arachidicola* (synonym *M. arachidis* or *Cercospora arachidis*) and *M. berkeleyi* on peanuts, *M. pisi* on peas, and *M. brassiciola* on *Brassicae*; cabbage (e.g., *P. brassicae*), rapeseed (e.g., *P. parasiticus*). Downy mildew species (Peronospora) on parasitica, onions (e.g., P. destructor), tobacco (P. tabacina), and soybeans (e.g., P. manshurica); soybean rust fungi such as P. meibomiae and P. meibomiae (soybean rust); Phialophora species, such as on vines (e.g., P. tracheiphila and P. tetraspora) and soybeans (e.g., P. gregata: stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and L. maculans: root and stem rot) on rapeseed and cabbage, and P. beetroot on sugar beets. betae (root rot, leaf spot, and damping-off), and P. zeae-maydis (synonym Phyllosticazeae) on maize; Phomopsis species on sunflowers, vines (e.g., P. viticola: vine and leaf spot) and soybeans (e.g., stem rot: P. phaseoli, sexual form: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora species on various plants (wilt, root, leaf, fruit, and stem rot), such as red peppers and gourds (e.g., Phytophthora capsici).*Phytophthora capsici*, soybeans (e.g., *P. megasperma*, synonym *P. sojae*), potatoes and tomatoes (e.g., *P. infestans*: late blight), and broadleaf trees (e.g., *P. ramorum*: sudden death of oak trees); *Plasmodiophora brassicae* (club root) on cabbage, rapeseed, radish, and other plants; *Plasmopara* species, such as *P. viticola* (grape downy mildew) on vines and *P. halstedii* on sunflowers; *Podosphaera* species (powdery mildew) on Rosaceae plants, hops, pome, and soft fruits, such as *P. white podosphaera* on apples. *Pseudocercosphaera* on gourds and *P. xanthii* on gourds; *Polymyxa* species on cereals such as barley and wheat (*P. graminis*) and sugar beets (*P. betae*), and viral diseases transmitted by these; *Pseudocercosporella herpotrichoides* (synonyms *Oculimaculayallundae*, *O. acuformis*: eye spot, sexual form: *Tapesia yallundae*) on cereals such as wheat or barley; *Pseudoperonospora* (downy mildew) on various plants, such as *P. cubensis* on gourds or *P. humili* on hops; *Pseudopezicula tracheiphila* (red fire disease) on vines. Disease) or rotbrenner, asexual form: genus *Phialophora*; species of the genus *Puccinia* (rust diseases) on various plants, such as *P. triticina* (brown rust or leaf rust) on cereals (such as wheat, barley, or rye), *P. striiformis* (stripe rust or yellow rust), *P. hordei* (dwarf rust) on barley, *P. graminis* (stem rust or black rust) or *P. recondita* (brown rust or leaf rust), *P. kuehnii* (citrus rust) on sugarcane, and *P. asparagus* species on asparagus.asparagi); species of the genus *Pyrenopeziza*, such as *P. brassicae* on rapeseed; *Pyrenophora tritici-repentis* (asexual form: *Drechslera tritici-repentis*) (brown spot) on wheat or *P. teres* (net blotch) on barley; species of the genus *Pyricularia*, such as *P. oryzae* (sexual form: *Magnaporthe grisea*) on rice, and *P. grisea* on turfgrass and cereals; species of the genus *Pythium* (damping-off) on turfgrass, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables, and many other plants (e.g., *P. truncatula*). *Pythium ultimum* or *P. aphanidermatum* and *P. oligandrum* on mushrooms; *Ramularia* species, such as *R. collo-cygni* on barley (*Ramularia* leaf spot, physiological leaf spot), *R. areola* on cotton (sexual form: *Mycosphaerella areola*), and *R. beticola* on sugar beets; *Rhizoctonia* species on cotton, rice, potato, bulrush, corn, rapeseed, sugar beets, vegetables, and many other plants, such as *R. solani* on soybean (*Rhizoctonia* root and stem rot), and *R. solani* on rice. *Rhizopus solani* (sheath blight) or *Rhizopus cerealis* (rhizopus leaf blight) on wheat or barley; *Rhizopus stolonifer* (black mold, soft rot) on strawberries, carrots, cabbages, vines, and tomatoes; *Rhynchosporium secalis* and *R. commune* (scald) on barley, rye, and triticale; *Sarocladium oryzae* and *S. attenuatum* (sheath rot) on rice; *S. minor* and *S. sclerotiorum* on vegetables and field crops such as rapeseed, sunflower (e.g., *S. sclerotiorum*) and soybeans, and *S. sclerotinia* species (stem rot or white mold) on soybeans, peanuts, vegetables, corn, cereals, and ornamental plants.*Septoria* species on various plants, such as *S. glycines* on soybeans (for brown spot disease), *S. tritici* on wheat (for *Zymoseptoria tritici*, for *S. tritici* leaf spot), and *S. noodorum* on cereals (for *Stagonospora nodorum*, for *S. nodorum* leaf spot); *Uncinula necator* on vines (for *Erysiphe necator*, for powdery mildew, asexual form: *Oidium tuckeri*); and *Helminthosporium* on maize (for example, *S. turcicum*, for *Helminthosporium*). turcicum) and Setosphaeria species on turfgrass (leaf blight); maize (e.g., S. reiliana, synonym Ustilago reiliana: smut), Sphacelotheca species on sorghum and sugarcane (smut); Sphaerotheca fuliginea on gourd (synonym Podosphaera xanthii: powdery mildew); Spongosspora subterranea on potato (powdery mildew) and viral diseases transmitted by it; Stagonospora species on cereals, such as S. nodorum on wheat (spot blight, sexual form: Leptosphaeria) nodorum [synonyms: Phaeosphaerianodorum, Septoria nodorum]; syncytrium endobioticum on potatoes (potato canker); species of the genus Taphrina, such as T. deformans on peaches (leaf curl) and T. pruni on plums (plumpocket); species of the genus Thieviopsis on tobacco, pome, vegetables, soybeans, and cotton (black root rot), such as T. thielaviopsis.Basicola (synonym Chalara elegans); Tilletia species on grains (common bunt or stinking smut), such as T. tritici (synonym T. caries, wheat bunt) and T. controversa (wheat bunt); Trichoderma harzianum on mushrooms; Typhula incarnate (grey snow mold) on barley or wheat; Urocystis species, such as U. occulta (stem smut) on rye; vegetables such as beans (e.g., U. appendiculatus, synonym U. phaseoli), and sugar beets (e.g., U. appendiculatus). Rusts caused by *Uromyces* species on beans (e.g., *U. vignae*, *U. pisi*, *U. viciae-fabae*, and *U. fabae*) and dried beans (e.g., *U. vignae*, *U. pisi*, *U. viciae-fabae*, and *U. fabae*); and loose smut (*U. nuda* and *U. avaenae*), maize (e.g., *U. maydis*: maize smut), and sugarcane (*Ustilago* species). Scab; species of *Venturia* on apples (e.g., *V. inaequalis*) and pears (scab); and species of *Verticillium* on various plants such as fruits and ornamental plants, vines, soft fruits, vegetables, and field crops (wilt), such as *V. longisporum* on rapeseed, *V. dahliae* on strawberries, rapeseed, potatoes, and tomatoes, and *V. fungicola* on mushrooms; and *Syngonium spp.* on cereals.

[0197] Compound I and its compositions are particularly suitable for controlling pathogens of the following plant diseases: rust fungi on various plants (from the order Puccinales), preferably rust fungi on soybeans and cereals, more preferably selected from: *Puccinia graminis*, which causes Asian soybean rust on soybeans; *Puccinia graminis*, which causes stem rust or black rust on cereals; *P. triticina* (synonym *P. recondita*), which causes brown rust or leaf rust on wheat; *P. striiformis*, which causes yellow rust or stripe rust on wheat; *P. hordei*, which causes barley leaf rust; *P. sorghi*, which causes common maize rust; and *P. polysora*, which causes southern maize leaf rust.

[0198] Therefore, the present invention also relates to a method for treating plant pathogenic rust fungi (from the order Rustales), the method comprising: therapeutically and / or preventively treating infected plants at risk of being infected by said plant pathogenic rust fungi with an agricultural chemical composition comprising at least one compound of formula I at a dosage rate of 50 to 200 g / ha, and / or applying the agricultural chemical composition to said plant pathogenic fungi, more preferably, in said method, the plants being selected from soybeans and cereals.

[0199] In addition, Compound I and its compositions are particularly suitable for controlling other pathogens of plant diseases caused by plant pathogenic fungi, wherein at least a portion of their populations have acquired the F129L mutation in the cytochrome b gene that confers resistance to Qo inhibitors: *Alternaria solani*, which causes early blight in Solanaceae plants; *Pyrenophora teres*, which causes barley spot disease; *Pyrenophora tritici-repentis*, which causes brown spot, yellow leaf spot, yellow leaf blight, or worm disease in cereals; and *Rhizoctonia solani*, which causes various plant diseases such as root rot, wilt, and nematode disease in a variety of plants.

[0200] In addition, Compound I and its compositions are particularly suitable for controlling pathogens of the following plant diseases: mildew on specialty crops, soybeans, rapeseed, and sunflowers (e.g., *Botrytis cinerea* on strawberries and vines, *Sclerotinia sclerotiorum*, *Sclerotinia pulveratum*, and *S. rolfsii* on rapeseed, sunflowers, and soybeans); Fusarium diseases on cereals (e.g., *Fusarium graminearum* and *Fusarium graminearum* on wheat); downy mildew on specialty crops (e.g., *Monosporium variegatum* on vines, *Phytophthora infestans* on potatoes); powdery mildew on specialty crops and cereals (e.g., *Hypericum variegatum* on vines, various powdery mildew species on specialty crops, *Erysiphe graminearum* on cereals); and leaf spot diseases on cereals, soybeans, and maize (e.g., *Syngonium valerate* and *Syngonium glomeratum* on cereals, *Syngonium glutamicum* on soybeans, and *Cercospora* species on maize and soybeans).

[0201] Fungicide-resistant strains of the aforementioned plant pathogenic fungi have been reported, and resistance to one or more fungicides from various modes of action, including but not limited to the following, has been observed through target site mutations: β-tubulin assembly inhibitors, sterol demethylation inhibitors (DMI), quinone exogenous inhibitors (Qol), and succinate dehydrogenase inhibitors (SDHI). Examples of mutation sites encoding such target proteins in each plant pathogenic fungus include those indicated in Table M below.

[0202] Table M:

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209] Therefore, compound I is particularly useful for controlling fungicide-resistant strains of plant pathogenic fungi as described in Table M. Such strains may possess one or more types of resistance derived from one or more mutations (including, but not limited to, mutations listed in Table M) of one or more genes encoding target proteins of various fungicides, and / or resistance derived from overexpression of the target proteins.

[0210] In addition, some fungal strains may have developed other types of resistance to fungicides, some of which are known as efflux-resistant multidrug-resistant fungi.

[0211] As used herein, the term "efflux-resistant multidrug-resistant fungus" refers to fungi that sometimes exhibit resistance to multiple fungicides through various fungicidal mechanisms of action, by overexpressing various membrane transport proteins present on the cell membrane and increasing the efflux pump function that transports plant disease control agents flowing into the cell to the extracellular space. Examples of membrane transport proteins include, but are not limited to, ABC transporters and MFS transporters. As used herein, "ABC transporter" refers to an ATP-binding cassette transporter, and "MFS transporter" refers to a major promoter superfamily transporter. Overexpression of membrane transporters is confirmed by conventional methods, such as by measuring the amount of the membrane transporter or the amount of mRNA corresponding to the gene encoding the membrane transporter.

[0212] Efflux-resistant multidrug-resistant fungi exhibit sufficient resistance to any plant disease control agents due to the overexpression of membrane transport proteins, regardless of the measured mRNA levels. The measured mRNA levels relative to wild-type fungi can be, for example, 5-fold, 20-fold, 100-fold, or more.

[0213] The method of this invention can be applied to the prevention and control of plant diseases caused by effusive multidrug-resistant fungi.

[0214] Ectopic multidrug-resistant fungi may also have one or more types of resistance derived from one or more mutations (including but not limited to the mutations listed in Table M) of one or more genes encoding target proteins of various fungicides and / or resistance derived from overexpression of the target proteins.

[0215] Therefore, compound I is also particularly useful for controlling such efflux-resistant multidrug-resistant fungi.

[0216] According to another embodiment of the invention, the invention also relates to the use of compounds of formula I for combating plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors. According to another embodiment of the invention, the invention also relates to a method for combating plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors, the method comprising: treating with an effective amount of at least one compound I or a composition comprising the compound the plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors, or materials, plants, soil, or seeds at risk of being attacked by plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors.

[0217] The term “plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors” should be understood as at least 10% of the fungal isolates to be controlled, more preferably at least 30%, even more preferably at least 50%, and most preferably at least 75% (particularly between 90% and 100%) of the fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors.

[0218] It has been observed under field conditions that populations of plant pathogenic fungi, clearly composed of non-resistant strains, can readily develop resistance. These compounds can also be applied under such conditions to completely prevent the formation of resistance and the spread of resistant strains. In this respect, it is useful that they also possess strong activity against non-resistant plant pathogenic fungi.

[0219] According to another embodiment, a method for combating plant pathogenic fungi includes: a) identifying plant pathogenic fungi containing a mutation in the mitochondrial cytochrome b gene that confers resistance to Qo inhibitors, as defined herein, or materials, plants, soil, or seeds at risk of being infected by such plant pathogenic fungi; and b) treating the fungi or materials, plants, soil, or seeds with an effective amount of at least one compound I or a composition containing the compound.

[0220] According to another embodiment of the present invention, the present invention also relates to a method for combating plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors, the method comprising: treating with an effective amount of at least one compound I or a composition comprising the compound the material, plant, soil or seed at risk of being infested by plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors; more preferably at least 30%, even more preferably at least 50%, and most preferably at least 75% of the fungus containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors.

[0221] According to one embodiment of the use and method for combating plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors, the mutation in the mitochondrial cytochrome b gene of these plant pathogenic fungi is G143A.

[0222] The mutation G143A in the cytochrome b (cytb, also known as cob) gene should be understood to refer to any substitution of the nucleotide at codon 143 (glycine; e.g., GGT, GGC, GGA, or GGG) encoding "G", resulting in a substitution at codon 143 (alanine; e.g., GCT, GCC, GCA, or GCG) encoding "A". For example, replacing the second nucleotide 'G' at codon 143 in the cytochrome b gene with 'C' (GGT to GCT) would result in a single amino acid substitution (G143A) at position 143 of the cytochrome b protein (Cytb) from G (glycine) to A (alanine). In this invention, the mutation G143A in the cytochrome b gene should be understood as a single amino acid substitution (G143A) at position 143 of the cytochrome b protein from G (glycine) to A (alanine).

[0223] According to another embodiment, plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors (wherein the mutation in the mitochondrial cytochrome b gene of these plant pathogenic fungi is G143A) are selected from the group consisting of: Alternaria alternata, Powdery mildew of the grass family, Pyriculania oryzae (also known as Grey-spotted Alternaria), Phyllostachys oryzae (also known as Gramineae), Phyllostachys feijiensis, Acer maculatus, Cynostomium rotundifolium, Sclerotium sclerotium var. oryzae, and Staphylococcus aureus, particularly Phyllostachys oryzae.

[0224] According to another embodiment of the use and method for combating plant pathogenic fungi containing mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors, the mutation in the mitochondrial cytochrome b gene of these plant pathogenic fungi is F129L.

[0225] The mutation F129L in the cytochrome b (cytb, also known as cob) gene should be understood to refer to any substitution of the nucleotide at codon 129 (phenylalanine; e.g., TTT or TTC) encoding "F", which results in a substitution at the codon encoding "L" (leucine; e.g., TTA, TTG, TTG, CTT, CTC, CTA, or CTG). For example, replacing the first nucleotide 'T' of codon 129 in the cytochrome b gene with 'C' (TTT to CTT) would result in a single amino acid substitution (F129L) at position 129 of the cytochrome b protein, from F (phenylalanine) to L (leucine). In this invention, the mutation F129L in the cytochrome b gene should be understood as a single amino acid substitution (F129L) at position 129 of the cytochrome b protein, from F (phenylalanine) to L (leucine).

[0226] Many other plant pathogenic fungi have acquired the F129L mutation in the cytochrome b gene, conferring resistance to Qo inhibitors, such as rust fungi, particularly soybean rust (Alternaria beaninae and Alternaria spp.), and fungi from the genera *Alternaria*, *Sclerotium*, and *Rhizoctonia*. Preferred fungal species are *Alternaria solanacea*, *Alternaria beaninae*, *Sclerotium spp.*, *Sclerotium spp.*, *Sclerotium spp.*, *Sclerotium spp.*, *Sclerotium spp.*, and *Rhizoctonia solani*; especially *Alternaria beaninae*.

[0227] In one aspect, the present invention relates to a method for protecting plants susceptible to and / or attacked by plant pathogenic fungi containing an amino acid substitution F129L in the mitochondrial cytochrome b protein that confers resistance to Qo inhibitors. The method comprises applying to the plant a compound of at least one formula I or a composition containing at least one formula I, treating plant propagation material of the plant with a compound of at least one formula I or a composition containing at least one formula I, and / or applying to the plant pathogenic fungi a compound of at least one formula I or a composition containing at least one formula I.

[0228] According to another embodiment, a method for combating plant pathogenic fungi includes: a) identifying plant pathogenic fungi containing F129L amino acid substitutions in mitochondrial cytochrome b protein that confer resistance to Qo inhibitors, as defined herein, or materials, plants, soil, or seeds at risk of being infected by these plant pathogenic fungi; and b) treating the fungi or materials, plants, soil, or plant propagation material with an effective amount of at least one compound of formula I or a composition containing the compound.

[0229] The term "plant pathogenic fungus containing F129L amino acid substitutions in mitochondrial cytochrome b protein that confer resistance to Qo inhibitors" should be understood as at least 10% of the fungal isolate to be controlled, preferably at least 30%, more preferably at least 50%, even more preferably at least 75%, most preferably between 90% and 100%, and particularly between 95% and 100%, of the fungus containing such F129L substitutions in mitochondrial cytochrome b protein that confer resistance to Qo inhibitors.

[0230] Compound I and its compositions are also suitable for the prevention and control of harmful microorganisms in the protection of stored products or harvests and in the protection of materials.

[0231] The term "stored product or harvest" should be understood to refer to natural substances of plant or animal origin and their processing forms desired for long-term preservation. Plant-derived stored products, such as stems, leaves, tubers, seeds, fruits, or grains, can be preserved in their freshly harvested state or through processing methods such as pre-drying, moistening, crushing, grinding, pressing, or baking (processing also known as post-harvest treatment). Timber also falls under the definition of stored products, whether in log form, such as construction timber, transmission towers, and fences, or in finished product form, such as furniture or objects made of wood. Animal-derived stored products are hides, leather, fur, hair, etc. Preferably, "stored product" should be understood to refer to natural substances of plant origin and their processing forms, more preferably fruits and their processing forms, such as pome, stone fruit, soft fruit, and citrus fruits and their processing forms, wherein the application of compound I and its combinations can also prevent adverse effects such as rot, discoloration, or mold.

[0232] The term “protection of materials” should be understood to mean protecting technical and non-living materials such as adhesives, glues, wood, paper, cardboard, textiles, leather, paint dispersions, plastics, coolant lubricants, fibers, or fabrics from contamination and damage by harmful microorganisms such as fungi and bacteria.

[0233] When used for the protection of materials or stored products, the amount of active substance applied depends on the type of application and the desired effect. Typically, the amount applied for the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of treated material.

[0234] Compound I and its compositions can be used to improve plant health. The present invention also relates to a method for improving plant health by treating plants, their propagation material, and / or the sites where plants are growing or will grow, respectively, with effective amounts of Compound I and its compositions.

[0235] The term "plant health" should be understood as referring to the condition of plants and / or their products, determined by multiple indicators, individually or in combination, such as yield (e.g., increased biomass and / or increased content of valuable components), plant vigor (e.g., improved plant growth and / or greener leaves ("greening effect")), quality (e.g., improved content or composition of certain components), and tolerance to abiotic and / or biotic stresses. These plant health indicators may be interdependent or mutually influential.

[0236] Compound I is used as is or in combination form to treat fungi with an effective amount of the active substance, protecting plants, plant propagation material (such as seeds), soil, surfaces, materials, or rooms from fungal infection. Application can be carried out before or after the plants, plant propagation material (such as seeds), soil, surfaces, materials, or rooms are infected with fungi.

[0237] Agricultural chemical compositions contain a fungicide-effective amount of compound I. The term "fungicide-effective amount" refers to the amount of a composition or compound I sufficient to control harmful fungi on cultivated plants, or in the protection of stored products or harvests, or in the protection of materials, without causing substantial damage to the treated plants, stored products or harvests, or treated materials. This amount can vary widely and depends on various factors such as the fungal species to be controlled, the treated cultivated plants, stored products, harvests or materials, climatic conditions, and the specific compound I used.

[0238] Plant propagation material may be preventively treated with compound I itself or a composition containing at least one compound I during or before planting or transplanting.

[0239] When used for plant protection, the amount of active substance applied is 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha, and especially 0.1 to 0.75 kg / ha, depending on the type of effect desired.

[0240] In the treatment of plant propagation material (such as seeds), for example by dusting, coating or soaking, every 100 kg of plant propagation material (preferably seeds) requires an amount of active substance that is typically 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g and most preferably 5 to 100 g.

[0241] Users typically apply agricultural chemical compositions using pre-dose devices, backpack sprayers, spray cans, spray aircraft, or irrigation systems. Generally, the agricultural chemical composition is prepared to the desired application concentration using water, buffer solutions, and / or additional adjuvants, thus yielding a ready-to-use spray or agricultural chemical composition according to the invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of ready-to-use spray are applied per hectare of usable agricultural area.

[0242] Compound I and compositions containing them can be applied in conjunction with or utilizing smart agriculture technologies such as precision agriculture, remote and near-field imaging and image recognition, or smart agriculture site management programs. Such technologies typically include models, such as computer programs, that support users by considering information from various sources to increase the quality and yield of harvested materials, reduce pest damage, including the prediction of pest stress and the intelligent application of crop protection products, ensure environmental protection, support rapid and reliable agronomic decision-making, reduce the use of fertilizers and crop protection products, reduce product residues in consumer products, increase the spatial and temporal accuracy of agronomic measures, automate processes, and enable traceability of measures. Commercially available systems that include agronomic models include, for example, FieldScripts™ (The Climate Corporation), Xarvio™ (BASF), and AGLogic™ (John Deere).

[0243] The information inputs for these models include, but are not limited to, soil data, information about plants (including crops and / or unwanted vegetation) currently growing in or likely to grow in the area of ​​interest, weather information, information about the location of the area and information that can be directly derived from it, information about pest stress, information about beneficial organisms (including predicted and current ones), and / or historical information on any of the above.

[0244] Information that can be used in precision agriculture can be based on input from at least one user, accessed from external data sources and databases, or based on sensor data. Data sources typically include short-range detection systems, such as soil sensors, and remote sensing, which can be achieved, for example, through imaging by unmanned aerial vehicles such as drones or satellites. Sensors can be included in Internet of Things (IoT) systems and can be directly or indirectly connected to processing units, for example via wireless networks and / or cloud applications. Typically, at least one processing unit will take this information into account and use it to provide recommendations and generate control signals.

[0245] Typical technologies used in smart agriculture include automated control robots (such as tractors, harvesters, and drones), artificial intelligence (such as machine learning), imaging technology (such as image segmentation), big data analytics, model generation, cloud computing, and machine-to-machine communication.

[0246] Precision agriculture, such as precision farming, is characterized by the targeted application of active ingredients like pesticides, plant growth regulators, fertilizers, and / or water, analyzed spatially and / or temporally. This includes variations in application rates at agronomic sites, regions, or specific locations, and variations in the targeted planting or sowing of desired plant propagation material at agronomic sites in a spatially and / or temporally analyzed manner. Precision agriculture typically involves using geolocation technologies like GPS to acquire information about the location and boundaries of areas of interest, the application equipment used, the sensors employed, and the recorded data, and to control the actions of agricultural vehicles, such as spraying. By combining geolocation data with (digital) maps, it becomes possible to perform (semi-)automated agricultural practices at locations of interest, such as through the use of (semi-)automated spraying or sowing equipment.

[0247] Precision agriculture typically includes the application of smart spraying equipment, such as spot spraying; and precision spraying on farms, such as via irrigation systems, tractors, robots, helicopters, airplanes, and unmanned aerial vehicles (UAVs). Such equipment typically includes input sensors (e.g., cameras) and a processing unit configured to analyze input data and to provide recommendations or decisions based on the analysis of the input data to apply Compound I or compositions containing them to agronomic sites, such as soil, crop plants, or to control pests in a specific and precise manner. For example, pest detection, identification, and / or classification can be performed in images acquired by a camera. Such identification and / or classification can utilize image processing algorithms that may employ artificial intelligence (e.g., machine learning algorithms) or decision trees. In this way, Compound I or compositions described herein can be applied only at the desired location, time point, and dosage rate.

[0248] Compound I, its N-oxide, and salt can be converted into commonly used types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, tablets, capsules, and mixtures thereof. Examples of composition types (see also "Catalogue of pesticide formulation types and international coding system", Technical Monograph, Vol. 2, 6th edition, May 2008, CropLife International) are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials (such as seeds). These compositions are prepared in known ways, such as those described in: Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The present invention also relates to agrochemical compositions comprising an adjuvant and at least one compound I.

[0249] Suitable additives include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, viscous agents, and binders.

[0250] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylnaphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, and glycol; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof.

[0251] Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; and plant-derived products, such as cereal flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0252] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or auxiliaries. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American edition).

[0253] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts, or ammonium salts of sulfonates, sulfates, phosphates, and carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0254] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated by 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, with ethylene oxide being preferred. Examples of N-substituted fatty acid amides are fatty acid glucosamides or fatty acid chain alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homologs or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0255] Suitable cationic surfactants are quaternary ammonium surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers containing alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.

[0256] Suitable adjuvants are compounds that possess negligible or no biocidal activity themselves and enhance the biological performance of compound I against the target. Examples include surfactants, mineral or vegetable oils, and other adjuvants, such as those listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5. Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable defoamers are silicones, long-chain alcohols, and salts of fatty acids. Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium dioxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants). Suitable thickeners or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biowaxes or synthetic waxes, and cellulose ethers.

[0257] Agricultural chemical compositions typically contain, by weight, an active substance (e.g., at least one compound I) at a concentration between 0.01% and 95%, preferably between 0.1% and 90%, more preferably between 1% and 70%, and particularly between 10% and 60%. Agricultural chemical compositions typically contain, by weight, at least one adjuvant at a concentration between 5% and 99.9%, preferably between 10% and 99.9%, more preferably between 30% and 99%, and particularly between 40% and 90%. The active substance (e.g., compound I) is used with a purity of 90% to 100%, preferably 95% to 100% (based on NMR spectra).

[0258] For the purpose of treating plant propagating material, especially seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are commonly used. After dilution by 2 to 10 times, the concentration of the active ingredient in the ready-to-use formulation of the compositions under discussion is 0.01% to 60% by weight, preferably 0.1% to 40%. Application can be carried out before or during sowing. Methods for applying compound I and its compositions to plant propagating material, especially seeds, include seed dressing, coating, granulation, dusting, soaking, and furrow application. Preferably, compound I or its compositions are applied to the plant propagating material by methods that do not induce germination, such as seed dressing, granulation, coating, and dusting.

[0259] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients, as well as other pest control agents (e.g., fungicides, growth regulators, herbicides, insecticides, safeners) can be added as premixes to Compound I or its compositions, or added only before use (tank mix). These agents can be blended with the compositions according to the invention at a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0260] Pesticides are generally chemical or biological agents (such as pest-killing active ingredients, compounds, compositions, viruses, bacteria, antimicrobial agents, or disinfectants) that prevent, disable, kill, or otherwise thwart pests through their effects. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that damage property, cause disturbances, spread diseases, or act as vectors for diseases. The term "pesticide" also includes plant growth regulators that alter the expected growth, flowering, or reproductive rate of plants; defoliants that cause leaves or other foliage to fall off the plant, generally promoting harvest; desiccants that promote the drying of living tissues, such as unwanted above-ground parts of plants; plant activators that activate plant physiological functions to defend against certain pests; safeners that reduce the unwanted herbicidal effects of pesticides on crop plants; and plant growth promoters that affect plant physiological functions, such as enhancing plant growth, biomass, yield, or any other quality parameter of the harvestable product of the crop plant.

[0261] Biopesticides are defined as pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (US Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two main categories: microbial and biochemical pesticides.

[0262] (1) Microbial pest control agents consist of bacteria, fungi, or viruses (and typically include metabolites produced by bacteria and fungi). Insecticidal nematodes are also classified as microbial pest control agents, although they are multicellular.

[0263] (2) Biochemical pesticides are naturally occurring substances that are relatively nontoxic to mammals, and are used to control pests or provide other crop protection purposes as defined below.

[0264] In many cases, mixing compound I, used as a fungicide, or compositions containing it, with other fungicides results in the broadening of the fungicidal activity spectrum or the prevention of the development of fungicide resistance. Furthermore, in many cases, synergistic effects (synergistic mixtures) are achieved.

[0265] The following list of biocides II that can be used in combination with compound I is intended to illustrate possible combinations, but does not limit them:

[0266] A) Respiratory depressants

[0267] -in Q oSite-specific complex III inhibitors: azoxystrobin (A.1.1), fenoxystrobin (A.1.2), eugenol (A.1.3), azoxystrobin (A.1.4), fenoxystrobin (A.1.5), fenoxystrobin (A.1.6), fenoxystrobin (A.1.7), flufenoxystrobin (A.1.8), azoxystrobin (A.1.9), mandestrobin (A.1.9) A.1.10), fenoxyfen (A.1.11), oxadiazon (A.1.12), azoxystrobin (A.1.13), azoxystrobin (A.1.14), azoxystrobin (A.1.15), azoxystrobin (A.1.16), oxadiazon (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylaminooxymethyl)-phenyl)-2-methoxyimino-N-methylacetamide (A.1.18), pyraclostrobin (A.1.10), fenoxystrobin (A.1.11), fenoxystrobin (A.1.12), fenoxystrobin (A.1.13), fenoxystrobin (A.1.14), fenoxystrobin (A.1.15), fenoxystrobin (A.1.16), fenoxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), pyraclostrobin (A.1.19). 19) Chlorpyrifos (triclopyricarb / chlorodincarb) (A.1.20), Oxadiazon (A.1.21), Imidacloprid (A.1.21), Methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazole-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), Tetracycline (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl] [-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyrimethanil (A.1.36), pyraclostrobin (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxymethyl acrylate (A.1.38);

[0268] -in Q i Site-specific complex III inhibitors: cyazofamid (A.2.1), indoxofensulfuron (A.2.2), 2-methylpropionic acid [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridin-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonon-7-yl] ester (A.2.3), fenpicoxamid (A.2.4), pyridine (A.2.5), metarylpicoxamid (A.2.6);

[0269] - Complex II inhibitors: Benzac-methyl (A.3.1), Benzoflufenicol (A.3.2), Bifenpyroxime (A.3.3), Cyclopyroxime (A.3.4), Mancozeb (A.3.5), Mefenoxam (A.3.6), Fluopyram (A.3.7), Fluopyram (A.3.8), Fluopyram (A.3.9), Furazolidone (A.3.10), Isopropylthiamethoxam (A.3.11), Pyraclostrobin (A.3.12), Mefenoxam (A.3.13), Oxycarboxim (A.3.14), Fluopyram (A.3.15), Pyraclostrobin (A.3.16), Fluopyram (A.3.17) Bifenazate (A.3.18), fluoxastrobin (A.3.19), chlorothalonil (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluoxastrobin (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methylpyrazol-4-carboxamide (A.3.29), (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoic acid methyl ester (A.3.30), isoflucypram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indane-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethyl-indane-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indane-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indane-4-yl]pyridine-3-carboxamide (A.3.35) A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indamino-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indamino-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indamino-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indamino-4-yl]pyridine-3-carboxamide (A.3.39), trifluoropyridineamine (A.3.24);

[0270] - Other respiratory depressants: diflubenzuron (A.4.1); nitrophenyl derivatives: acaricides (A.4.2), fenpropathrin (A.4.3), fenpropathrin (A.4.4), fluazinam (A.4.5), fenpropathrin (A.4.6), pyraclostrobin (A.4.7); organometallic compounds: triphenyltin salts, such as triphenyltin acetate (A.4.8), triphenyltin chloride (A.4.9), or triphenyltin hydroxide (A.4.10); azoxystrobin (A.4.11); silthiamethoxam (A.4.12);

[0271] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0272] -C14 demethylase inhibitors: Triazoles: Penticazole (B.1.1), Bifenthrin (B.1.2), Fenoxacillin (B.1.3), Cycloconazole (B.1.4), Oxadiazon (B.1.5), Tebuconazole (B.1.6), Tebuconazole-M (B.1.7), Flutriafol (B.1.8), Cyproconazole (B.1.9), Fluquinazole (B.1.10), Flusilazole (B.1.11), Tebuconazole (B.1.12), Hexaconazole (B.1.13), Ammonium oxychloride (B.1.14), Izoxystrobin (B.1.15), Imidacloprid (B.1.17), Cyproconazole (B.1.18), Oxamidazole (B.1.19), Paclobutrazol (B.1.20), Tebuconazole (B.1.21), Propiconazole (B.1.22), Prothioconazole (B.1.23), Silosovirazole (B.1.24), Tebuconazole (B.1.25), Flufenoxuron (B.1.26) .1.26), triadimefon (B.1.27), azoxystrobin (B.1.28), cymoxanil (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]prop-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ol (B.1.32), fluopyram (B.1.33), isothiazine Fluopyram (ipfentrifluconazole) (B.1.37), chlorfenapyr (B.1.38), (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: acetamiprid (B.1.43) .1.44), isoprothiolane (B.1.45), prochloraz (B.1.46), fluconazole (B.1.47); pyrimidines, pyridines, piperazines: chlorophenylpyrimidinol (B.1.49), pyridabenoxime (B.1.50), azithromycin (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (B.1.55);

[0273] -δ14-reductase inhibitors: 4-dodecyl-2,6-dimethylmorpholine (aldimorph) (B.2.1), morpholine (B.2.2), morpholine acetate (B.2.3), butylmorpholine (B.2.4), clindamycin (B.2.5), benzyl sulfadiazine (B.2.6), fenvalerate (B.2.7), spirocyclophosphamide (B.2.8);

[0274] -3-Ketoreductase inhibitor: Cyclocyclam (B.3.1);

[0275] - Other sterol biosynthesis inhibitors: chlorfenapyrazole (B.4.1);

[0276] C) Nucleic acid synthesis inhibitors

[0277] - Phenylamide or acyl amino acid fungicides: Benalaxyl (C.1.1), Benalaxyl-M (C.1.2), Kiralaxyl (C.1.3), Metalaxyl (C.1.4), Metalaxyl-M (C.1.5), Furazolidone (C.1.6), Oxyxamic acid (C.1.7);

[0278] Other nucleic acid synthesis inhibitors: oxamyl (C.2.1), octathiazide (C.2.2), oxaquinic acid (C.2.3), ethirimol sulfonate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidine-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidine-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidine-4-amine (C.2.8);

[0279] D) Inhibitors of cell division and cytoskeleton

[0280] - Microtubule inhibitors: Benomyl (D.1.1), Carbendazim (D.1.2), Mefenoxam (D.1.3), Thiophanate-methyl (D.1.4), Methylthiophanate (D.1.5), Pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]butyramide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthioalkyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)butyramide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)- 2-Methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-propyl-butyramide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthioalkyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)-2-methylthioalkyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazole-3-amine (D.1.16);

[0281] Other cell division inhibitors: ethoxysulfuron (D.2.1), thiamethoxam (D.2.2), pendimethalin (D.2.3), fluopyram (D.2.4), benomyl (D.2.5), benzoyl sulfide (D.2.6), pyriofenone (D.2.7), and cyazofamid (D.2.8);

[0282] E) Inhibitors of amino acid and protein synthesis

[0283] - Methionine synthesis inhibitors: pyrimethanil (E.1.1), pyrimethanil (E.1.2), pyrimethanil (E.1.3);

[0284] - Protein synthesis inhibitors: blastomycin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), midomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);

[0285] F) Signal transduction inhibitors

[0286] -MAP / histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

[0287] -G protein inhibitor: Quinoxaline (F.2.1);

[0288] G) Lipid and membrane synthesis inhibitors

[0289] - Phospholipid biosynthesis inhibitors: Kefensan (G.1.1), Isoprothiolane (G.1.2), Dimethoate (G.1.3), Isoprothiolane (G.1.4);

[0290] -Lipid peroxidation: chloronitrobenzene (G.2.1), pentachloronitrobenzene (G.2.2), tetrachloronitrobenzene (G.2.3), methyl thiamethoxam (G.2.4), biphenyl (G.2.5), dimethoate (G.2.6), chlorazolamide (G.2.7), zinc thiazolidinedione (G.2.8);

[0291] - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumethomorph (G.3.2), dimethomorph (G.3.3), buprofen (G.3.4), bensulfuron-methyl (G.3.5), isopyram (G.3.6), valafenamide (G.3.7);

[0292] - Compounds and fatty acids that affect cell membrane permeability: cymoxanil (G.4.1);

[0293] -Oxidized sterol-binding protein inhibitors: Fluoxapiprolin (G.5.1), Fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methyl-pyrazole-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthyl-1-yl-pyridin-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acet ... [Acyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]- N-Tetrahydronaphthyl-1-ylpyridin-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthyl-1-ylpyridin-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthyl-1-ylpyridinyl 2-Carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.11);

[0294] H) Inhibitors with multi-site action

[0295] -Inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);

[0296] -Thio- and dithiocarbamates: ferric sulfate (H.2.1), mancozeb (H.2.2), mancozeb (H.2.3), thiamethoxam (H.2.4), mancozeb (H.2.5), methyl mancozeb (H.2.6), thiram (H.2.7), mancozeb (H.2.8), thiram (H.2.9);

[0297] - Organochlorine compounds: Dichlorophenoxyacetic acid (H.3.1), Chlorothalonil (H.3.2), Captan (H.3.3), Captan (H.3.4), Captan (H.3.5), Bacteriostatic agent (H.3.6), Dichlorophenol (H.3.7), Hexachlorobenzene (H.3.8), Pentachlorophenol (H.3.9) and its salts, Tetrachlorophthalide (H.3.10), Para-methyl thiophanate (H.3.11);

[0298] -Guinea and others: guanidine (H.4.1), dextrin (H.4.2), dextrin free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), guazatamine (H.4.6), guazatamine triacetate (H.4.7), guazatamine trioctylbenzene sulfonate (H.4.8), dithiazolinone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiacino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10);

[0299] I) Cell wall synthesis inhibitors

[0300] - Dextran synthesis inhibitors: Activamycin (I.1.1), Polyoxin B (I.1.2);

[0301] - Melanin synthesis inhibitors: quinolones (I.2.1), tricyclazole (I.2.2), propiconazole (I.2.3), dicyclomet (I.2.4), and isoprothiolane (I.2.5);

[0302] J) Plant defense inducers

[0303] -Aranoic acid benzene-S-methyl (J.1.1), thiabendazole (J.1.2), isothiazine (J.1.3), thiabendazole (J.1.4), cyclohexane-calcium (J.1.5); Phosphonates: ethphosphonic acid (J.1.6), ethphosphonium aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10);

[0304] K) Unknown mode of action

[0305] - Bronitrofon (K.1.1), acaricide (K.1.2), cycloflufenoxam (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), imazalil (K.1.6), diclofenac (K.1.7), pyridaben (K.1.8), sphalosporin (K.1.9), sphalosporin-methyl sulfate (K.1.10), diphenylamine (K.1.11), seed dressing ester (K.1.12), pyraclostrobin (K.1.13), flumetover (K.1.14), flumetylsulforim (K.1.60), sulfadiazine (K.1.15), fluthiazolinium (K.1.15) .1.16), hypersensitive protein (K.1.17), sulfadiazine (K.1.18), trichloromethylpyridine (K.1.19), phthalimide (K.1.20), tolprocarb (K.1.21), quinoline copper (K.1.22), propoxyquin (K.1.23), seboctylamine (K.1.61), tebufloquin (K.1.24), chlorothalonil (K.1.25), azoxystrobin (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylmethyl Amidone (K. 1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidin (K. 1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methylformamidin (K. 1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methylformamidin (K. 1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl N-Methyl-formamidinium (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexyloxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidinium (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidinium (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methyl-formamidinium (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methyl-formamidinium (K.1.34).35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-alkynoxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (pyridoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), (Z)-3-amino-2-cyano-3-phenyl 2-Acrylate-2-enoic acid ethyl ester (K.1.40), tetrazolium pyridine ester (K.1.41), N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate pentyl ester (K.1.42), N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-kyneyl ester (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), thiamethoxam (K.1.48), bromodiphenyl ether (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin (K.1.53), azoxystrobin (K.1.54), fluopyram (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)] [3-pyridyl]-N-ethyl-N-methylformamidin (K. 1.56), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methylformamidin (K. 1.57), flufenoxadiazam (K. 1.58), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide (K. 1.59), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (K. 1.60; WO 2018 / 177894, WO 2020 / 212513), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propionamide (K.1).62), 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K. 1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K. 1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]butyramide (K. 1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propionamide (K. 1.66) ), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1,1-diethyl-3-[[4-[5-[trifluoromethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K.1.69), N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K.1.70), 1-methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidone-2-one (K.1.72), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] [Methyl]isoxazolidin-3-one (K. 1.75), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K. 1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K. 1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K. 1.78), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K. 1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azacycloheptane-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-2-one (K.1.82), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (K.1.83), N-methyl- 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K. 1.84), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]-1H-1,2,4-triazol-3-amine (K. 1.85), N-methoxy-N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K. 1.86), propyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K. 1.87) N-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K. 1.88), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K. 1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K. 1.90), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K. 1.91), N-allyl-N-[[4-[ 5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (K. 1.92), N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]cyclopropaneformamide (K. 1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K. 1.94), N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin (K. 1.95), N'-[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin (K. 1.95).96) N'-[2-chloro-4-[(4-cyano-phenyl)methyl]-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin (K.1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-N-ethyl-N-methyl-formamidin (K.1.98);

[0306] L) Biological pest control agents

[0307] L1) Microbial agents with antifungal, antibacterial, antiviral, and / or plant defense activator activities: Powdery mildew parasiticus, Aspergillus flavus, Bacillus buddingus, Bacillus altissima, Bacillus amyloliquefaciens, Bacillus amyloliquefaciens subsp. plantae (also known as Bacillus belye), Bacillus megaterium, Bacillus mohaiweiii, Bacillus mycosis fungi, Bacillus pumilus, Bacillus simplex, Bacillus haematobium, Bacillus subtilis, Bacillus amyloliquefaciens var. subtilis, Bacillus belye, Candida oligosacchari, Candida saitoana, Clavibactermegia ichiganensis (bacteriophage), Shield mold, Cryptococcus parasiticus, Cryptococcus albus, Dilophosphora alopecuri, Fusarium oxysporum, Clonecrophys rosea f. catenulate (also known as Gliocladium) (catenulatum), pink bromoxynil, antibiotic lysinophil, mycolytic bromoxynil, drupocytosaccharomyces, microdochium dimerum, microsporum, Muscodor albus, Bacillus vesicularis, epiphytic Bacillus, polymyxa, pantothecin, Penicillium barometz, *Pseudomonas* species, *Pseudomonas leucosus*, *Pseudozyma flocculosa*, *Pichia aberrant*, *Pythium oligandrum*, *Sphaerodes mycoparasitica*, *Streptomyces glaucum*, *Streptomyces lidiflorus*, *Streptomyces purpureus*, *Trichoderma asperelloides*, *Trichoderma spp.*, *Trichoderma pellucida*, *Trichoderma galbana*, *T. harmatum*, *Trichoderma harzianum*, *T. polysporum*, *T. streptococcus*. stromaticum), Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Odman's sclerotium, Verticillium dahliae, and small zucchini yellow mosaic virus (non-toxic strain).

[0308] L2) Biochemical pest control agents with antifungal, antibacterial, antiviral and / or plant defense activator activities: hypersensitive protein, Polygonum cuspidatum extract;

[0309] L3) Microbial biocides with insecticidal, acaricidal, snail-killing, and / or nematicidal activity: *Agrobacterium radiata*, *Bacillus cereus*, *Bacillus stolonifer*, *Bacillus thuringiensis*, *Bacillus thuringiensis* subsp. *catella*, *Bacillus thuringiensis* subsp. *israelica*, *Bacillus thuringiensis* subsp. *wax moth*, *Bacillus thuringiensis* subsp. *kulstaq*, *Bacillus thuringiensis* subsp. *tenacylpyridae*, *Beauveria bassiana*, *Beauveria bassiana* species, *Burkholderia* species, and active purple bacteria (Chromobacterium). subtsugae), codling moth granulovirus (CpGV), pseudocodling moth granulovirus (CrleGV), species of Flavobacterium, bollworm nucleopolyhedrovirus (HearNPV), corn noctuid moth nucleopolyhedrovirus (HzNPV), corn noctuid moth monochroic nucleopolyhedrovirus (HzSNPV), *Heterobacter hygrophila*, *Cyclocarya flavum*, *Lecanicillium longisporum*, *L. muscarium*, *Metarhizium anisopliae*, *Metarhizium anisopliae* microsporum, *Metarhizium anisopliae* locust, *Nomura leishensis*, *Paecilomyces flavum*, *Paecilomyces lilacinus*, *Bacillus japonicus*, *Bacillus pastoris* species, *Paecilomyces szawa*, *Paecilomyces punctata*, *P. ramosa*, *P. thornea*, *P. ouss*. usgae), fluorescent pseudomonas, gray noctuid moth nucleopolyhedrovirus (SpliNPV), small leafroller nematode, small noctuid moth nematode, sawfly nematode, fresh yellow streptomyces, fine yellow streptomyces;

[0310] L4) Biochemical pest control agents with insecticidal, acaricidal, snail-killing, pheromone-based, and / or nematicidal activities: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-decadienoic acid ethyl ester (pear ester), (Z,Z,E)-7,11,13-hexadecanetrienal, heptyl butyrate, isopropyl myristate, lavender ester, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmone, (E,Z)-2,13-octadecadien-1-ol, acetic acid (E,Z) -2,13-octadecadien-1-ol ester, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone, (E,Z,Z)-3,8,11-tetradecadienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, Chenopodium ambrosiodes extract, neem oil, Quilay extract;

[0311] L5) Microbial pest control agents with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activities: Azotobacter agalactiae, Azotobacter brasiliensis, Azotobacter lipophila, Azotobacter iridozoensis, Azotobacter high-salt, Slow-growing rhizobia species, Slow-growing rhizobia ehrlich, Slow-growing rhizobia soybean, Slow-growing rhizobia lizardii, Slow-growing lupin rhizobia, Delfordia acidophila, Arbuscular mycorrhizal fungi, Mesophytic rhizobia species, Rhizobia pea biotype, Rhizobia pea clover biotype, Rhizobia pea broad bean biotype, Rhizobia tropicalis and Rhizobia spp. alfalfa;

[0312] O) Insecticides from categories O.1 to O.29

[0313] 0.1 Acetylcholinesterase (AChE) inhibitors: Aldicarb, fenvalerate, carbofuran, methylcarbate, methylcarbate, carbaryl, carbamate, carbofuran, methylcarbate, ethylcarbate, methylcarbate, imidacloprid, furazolidone, isoprocarb, imidacloprid, methomyl, fenvalerate, chlorpyrifos, propoxur, thiamethoxam, thiophanate-methyl, methylcarbate, XMC, imidacloprid, pymetrozine; Phosphate, methylpyridinium, ethyl phosphonate, phosmet, thiophanate-methyl, phosmet, chlorpyrifos, chlorpyrifos, methyl chlorpyrifos, phosmet, pyridaben, phosmet-S-methyl, diazinon, dichlorvos / DDVP, phosmet, dimethoate, methyl imidacloprid, ethylcarbate Phosphorus, EPN, ethion, propargite, phosmet, benzylphos, fenitrothion, fenthion, thiamethoxam, heptamethrin, cypermethrin, isopropylamine, O-(methoxyaminothio-phosphoryl)salicylic acid isopropyl ester, isoxazolium, malathion, phosmet, methamidophos, chlorpyrifos, phosmet, dibromophos, omethoate, sulfonium phosphate, parathion, methyl parathion, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, pyrazophos, pyridazine, quinalphos, phosmet, phosmet, butylpyrimidine, dithion, terbufos, chlorpyrifos, methyl ethion, triazophos, trichlorfon, phosmet.

[0314] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; acetamiprid, fipronil, butenpyram, pyrafluprole, pyriprole.

[0315] O.3 Sodium channel modulators: Flufenoxuron, Allethrin, Dextrorotatory-cis-trans Allethrin, Dextrorotatory-trans Allethrin, Bifenthrin, κ-Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl, Biobenzylfuran, Cypermethrin, Cypermethrin, β-Cypermethrin, Trifluralin, λ-Cypermethrin, γ-Cypermethrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, θ-Cypermethrin, ζ-Cypermethrin, Lambda-cypermethrin, Delanolyl, Enyne Pyrethroids, cypermethrin, deltamethrin, cypermethrin, cypermethrin, flufenoxuron, cypermethrin, t-flumethrin, bromoflumethrin, heptamethrin, imidacloprid, chlorflumethrin, methoxyfenozide, methoxyfenozide, ε-methoxyfenozide, permethrin, fenfluroxyfenozide, ethylanthrin, propargite, pyrethroids (pyrethrum), pyrethrum, flusilazole, heptamethrin, κ-heptamethrin, tetrafluoroethylene, pyrethroids, tetrabromopyrethrin, tetrafluoroethylene; DDT, methoxydichlorophenoxyacetic acid (DDT);

[0316] O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, thiamethoxam, cyclopyridamole, dinotefuran, imidacloprid, acetamiprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-epoxyethylenemethyl)-1H-imidazol-2-amine, (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylaminoguanidine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; flupyridine, flupyrflufenone, trifluralin, dithiazolinone;

[0317] 0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, ethyl spinosad;

[0318] 0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, rapamycin, mibamectin;

[0319] O.7 Juvenile hormone mimics: acetamiprid, acetamiprid, acetamiprid; phenoxycarb, fenvalerate;

[0320] O.8 Various non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; trichloronitromethane, sulfonyl fluoride, borax, tartaric acid;

[0321] O.9 Regulators of TRPV channels in string organs: pymetrozine, flufenoxuron;

[0322] O.10 Mite growth inhibitors: Tetradifon, Thiamethoxam, Fludex; Etoxazole;

[0323] O.11 Microbial disruptors of the intestinal membrane in insects: Bacillus thuringiensis, Bacillus sphaericus, and their insecticidal proteins: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis; Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;

[0324] O.12 Mitochondrial ATP synthase inhibitors: butyl ether urea; triazole tin, tricyclic tin, phenylbutyl tin, chlorfenapyr, trichlorfon;

[0325] O.13 Oxidative phosphorylation decoupling agents via proton gradient interference: brofentanil, DNOC, fipronil;

[0326] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: chlorpyrifos, fenitrothion, chlorpyrifos, dichlorvos;

[0327] O.15 Chitosan biosynthesis inhibitors type 0: bis(triflufenoxuron), flufenoxuron, diflufenoxuron, flucyclourea, flufenoxuron, flufenoxuron, lufenuron, flufenoxuron, polyfluorourea, flubendiamide, chlorfenapyr;

[0328] O.16 Chitosan biosynthesis inhibitor type 1: thiamethoxam;

[0329] O.17 Ecdyskin disruptor: cyromazine;

[0330] O.18 Ecdysone receptor agonists: methoxyfenozide, fenbufenozide, chlorfenapyr, furazolidone, cyclotebufenozide;

[0331] O.19 Octopus amine receptor agonist: Dimethicone;

[0332] O.20 Inhibitors of electron transport in mitochondrial complex III: flufenoxuron, cypermethrin, pyrimethanil, bifenazate;

[0333] O.21 Mitochondrial complex I electron transport inhibitors: quinclorac, azoxystrobin, pyrimethanil, pyridaben, pyridaben, acetamiprid, rotenone;

[0334] O.22 Voltage-dependent sodium channel blockers: indoxacarb, cyfluthrin, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene]-N-[4-(difluoromethoxy)phenyl]-hydrazinoamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]ethylene]-hydrazinoamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene]-N-[4-(difluoromethoxy)phenyl]-hydrazinoamide;

[0335] O.23 Acetyl-CoA carboxylase inhibitors: Spirodiclofen, Spirodiclofen, Spirodiclofen, Ethyl methoxypiperidine, Spirodiclofen diester, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azabispirol[4.2.4.2]tetradecano-11-en-10-one, and spirochete;

[0336] O.24 Mitochondrial complex IV electron transport inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

[0337] 0.25 Mitochondrial complex II electron transport inhibitors: pyridaben, fenflurfen, etoxazole;

[0338] 0.26 Rianotinamide receptor modulators: chlorantraniliprole, bromocyanamide, cyclobromocyanamide, flubendiamide, fluchlorfenapyr, (R)-3-chloro-N 1 -{2-Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-Methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N 1 -{2-Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-Methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazine carbamate; N-[4,6-dichloro-2-[(diethyl-λ-4-thionyl)carbamoyl]phenyl]-2-(3-chloro-2-pyridinyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-λ-4-thionyl)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridinyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl] [Phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; tetrachlorfenapyr; tetrazolium fenvalerate; thiofenoxam; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; chlorfenapyr; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide;

[0339] O.27: A modulator of the vocal organs: flupyradifurone;

[0340] O.28. Insecticidal compounds with unknown or uncertain modes of action: bispyribac-methyl, afranal, azadirachtin, sulfadiazine, fenproxetine, bromodiphenyl ether, fenproxetine, cryolite, cyproflanilid, dichloropyrimipyrimidine, trichlorfon, pyrimethanil, pyrimethanil, flumetoquin, fluthiamethoxam, fluhexafon, flupyradifon, flurranazine, metaldehyde, oxadiazon, synergist ether, pyrazolyl aniline, acetamiprid, tioxazafen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azabispirol[4]. 2.4.2]-Tetradecano-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]decano-3-en-2-one, 4-cyano-N-[2-cyano-5-[[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide, N-[5-[[[ 2-Chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2 -Cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methylbenzamide, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methylbenzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methylbenzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methylbenzamide,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, active substances based on Bacillus stolonifer (Votivo, I-1582); flupyriminin; trifluoroimidazamide; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro] -4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methylbenzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methylbenzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methylbenzamide; 2-(1,3-dioxane-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridinyl] ... Pyridine; 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridinyl)thiazolyl-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridinyl)thiazolyl-5-yl]pyridine-2-carboxamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2 3,5,6,7-Hexahydroimidazo[1,2-a]pyridine-5-ol; N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; 1-[(6-chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 2-(3-pyridyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; chlorpyrifos; saloranar, loteranar; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-Pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridinyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridinyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; isoxazolamide; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl) [4-[1-[1-[1-[4-(trifluoromethyl)pyrazole-3-carboxamide], N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; acynonapyr; benzpyrimoxan; tigolaner; oxazolylsulfonylpyridine; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R] [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate [Fluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazinyl]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazinyl]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazinyl]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,[4-Triazol-3-yl]phenyl]methylenehydrazinyl]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-3-methyl -6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridin-8-carboxylon, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]pyridine-2-yl ]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4-] ,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidone-1-yl]phenyl]methyl]cyclopropanecarboxamide; 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one; flupentixol, N-[3-chloro-1-(3-pyridyl)pyrazole-4-yl]-2-methylsulfonyl-propionamide, trifluoropyridineamine; 2-chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]pyrazole-4-yl]-N-cyclopropyl-pyridine-3-carboxamide; 2-chloro-5-[1-[2-chloro-4-[1,2,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]pyrazole-4-yl]-N-cyclopropyl-pyridine-3-carboxamide;2-Tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]pyrazol-4-yl]-N-cyclopropyl-pyridine-3-carboxamide; 5-[1-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]pyrazol-4-yl]-2-chloro-N-cyclopropyl-pyridine-3-carboxamide; N-[4- Chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, cyclopropionamide, cyclopropionamide; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione, 2-[2-fluoro- 4-Methyl-5-(2,2,2-trifluoroethylthioalkyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one, indazole, N-[4-chloro-2-(3-pyridyl)thiazolidin-5-yl]-N-ethyl-3-methylsulfonyl-propionamide, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-( [(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isooxazol-3-yl]-N-(pyrimidin-2-ylmethyl)isoquinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide;

[0341] O.29: Bromofluorobenzamide, Chlorfenapyramide.

[0342] The active substance referred to as component 2, its preparation, and its activity, for example, against harmful fungi, are known (see: https: / / pesticidecompendium.bcpc.org / ); these substances are commercially available. Compounds described by IUPAC nomenclature, their preparation, and their phytotoxic activity are also known (see Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE102005009458; US WO 00 / 29404; WO 00 / 46148; WO 00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431; WO 03 / 10149; WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145; WO 03 / 61388; WO 03 / 66609; WO 03 / 74491;WO 04 / 49804;WO 04 / 83193; WO 05 / 120234; WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624, WO 10 / 139271, WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514;WO 13 / 047749, WO 10 / 069882, WO 13 / 047441, WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224, WO 11 / 135833, CN1907024, CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024,WO09094442,WO WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441, WO 16 / 156241, WO16 / 162265). Some compounds are identified by their CAS registry number, which is divided into three parts by hyphens: the first part consists of two to seven digits, the second part consists of two digits, and the third part consists of a single digit.

[0343] At least one of the compounds in the above-listed list of pest control agents II is preferably mixed with at least one of the compounds I, which are explicitly disclosed herein (e.g., in the table), such as compounds I.1-A-1 to I.1-A-937, compounds I.2-A-1 to I.2-A-937, compounds I.3-A-1 to I.3-A-937, and example compounds 1 to 464.

[0344] According to the present invention, the solid material (dry matter) of biocidal agents (excluding oils such as neem oil) is considered the active component (e.g., obtained after drying or evaporation extraction or suspension in the case of liquid formulations of microbial agents). The weight ratios and percentages used for biological extracts such as soap extracts are based on the total weight of the dry content (solid material) of one or more of the respective extracts.

[0345] The total weight ratio of a composition containing at least one microbial pesticide in the form of live microbial cells (including dormant forms) can be determined by calculating the total weight of the corresponding active component using the following equation: 1 × 10⁻⁶ 10CFU equals the total weight of one gram of the corresponding active ingredient. Colony forming unit is a measure of living microbial cells. Furthermore, in the case of nematode biocides such as Steinernema feltiae, "CFU" can also be understood as the number of (juvenile) individual nematodes.

[0346] In binary mixtures, the weight ratio of component 1) to component 2) generally depends on the properties of the components used, typically in the range of 1:10,000 to 10,000:1, often in the range of 1:100 to 100:1, frequently in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1, and particularly in the range of 1:2 to 2:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally from 1000:1 to 1:1, often from 100:1 to 1:1, frequently from 50:1 to 1:1, preferably from 20:1 to 1:1, more preferably from 10:1 to 1:1, even more preferably from 4:1 to 1:1, and particularly in the range of 2:1 to 1:1. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 20,000:1 to 1:10, often from 10,000:1 to 1:1, frequently from 5,000:1 to 5:1, preferably from 5,000:1 to 10:1, more preferably from 2,000:1 to 30:1, even more preferably from 2,000:1 to 100:1, and particularly in the range of 1,000:1 to 100:1. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 1:1 to 1:1000, often from 1:1 to 1:100, frequently from 1:1 to 1:50, preferably from 1:1 to 1:20, more preferably from 1:1 to 1:10, even more preferably from 1:1 to 1:4, and particularly in the range of 1:1 to 1:2. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 10:1 to 1:20,000, often from 1:1 to 1:10,000, frequently from 1:5 to 1:5,000, preferably from 1:10 to 1:5,000, more preferably from 1:30 to 1:2,000, even more preferably from 1:100 to 1:2,000, and particularly in the range of 1:100 to 1:1,000.

[0347] In a ternary mixture, i.e., a composition comprising component 1), component 2), and compound III (component 3), the weight ratio of component 1) to component 2) depends on the characteristics of the active substance used, and is typically in the range of 1:100 to 100:1, often in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, and particularly in the range of 1:4 to 4:1, and the weight ratio of component 1) to component 3) is typically in the range of 1:100 to 100:1, often in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, and particularly in the range of 1:4 to 4:1. If necessary, any additional active ingredients may be added to component 1) at a ratio of 20:1 to 1:20. These ratios are also suitable for mixtures applied via seed treatment.

[0348] When mixtures containing microbial pesticides are used for crop protection, the application rate range is 1 × 10⁻⁶. 6 Up to 5 × 10 16 (or greater) CFU / ha, preferably 1 × 10 8 Up to 1 × 10 13 CFU / ha, and even more preferably 1 × 10 9 Up to 5 × 10 15 CFU / ha, and especially 1 × 10 12 Up to 5 × 10 14 CFU / ha. When nematodes are used as microbial pest control agents (e.g., *Nocturia stearothermia*), the application rate often ranges from 1 × 10⁻⁶. 5 Up to 1 × 10 12 (or larger), preferably 1 × 10 8 Up to 1 × 10 11 More preferably 5 × 10 8 Up to 1 × 10 10 Individual (e.g., in the form of egg, larva or any other living stage, preferably in the infetive larval stage) / ha.

[0349] When mixtures containing microbial pesticides are used for seed treatment, the application rate typically ranges from 1 × 10⁻⁶. 6 Up to 1 × 10 12 (or larger) CFU / seed, preferably 1 × 10 6 Up to 1 × 10 9 CFU / seed. Furthermore, the application rate for seed treatment is typically in the range of 1 × 10⁻⁶. 7Up to 1 × 10 14 (or larger) CFU / 100 kg seeds, preferably 1 × 10 9 Up to 1× 10 12 CFU / 100 kg of seeds.

[0350] Preferably, it is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group A) in Q. o The site-specific complex III inhibitor is more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.25), (A.1.34), and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.25), (A.1.34), and (A.1.35).

[0351] Also preferred is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group A) in Q. i The site-specific complex III inhibitor is more preferably selected from compounds (A.2.1), (A.2.3), (A.2.4) and (A.2.6); particularly selected from (A.2.3), (A.2.4) and (A.2.6).

[0352] Also preferred is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from complex II inhibitors of group A), and more preferably from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), and (A.3.38). and (A.3.39); in particular selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A. 3.22), (A.3.23), (A.3.24), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).

[0353] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from other respiratory inhibitors of group A), more preferably selected from compounds (A.4.5) and (A.4.11); particularly (A.4.11).

[0354] Also preferred is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from C14 demethylase inhibitors in component B), and more preferably from compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43), (B.1.46), (B.1.53), and (B.1.54). and (B.1.55); particularly selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and (B.1.46).

[0355] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from δ14-reductase inhibitors of component B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); especially (B.2.4).

[0356] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from phenylamide and acyl amino acid fungicides of group C), more preferably selected from compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and (C.1.4).

[0357] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from other nucleic acid synthesis inhibitors of group C), more preferably selected from compounds (C.2.6), (C.2.7) and (C.2.8).

[0358] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group D), more preferably from compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1.2), (D.1.5) and (D.2.6).

[0359] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group E), more preferably from compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); especially (E.1.3).

[0360] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group F), more preferably from compounds (F.1.2), (F.1.4) and (F.1.5).

[0361] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group G), more preferably from compounds (G.3.1), (G.3.3), (G.3.6), (G.5.1), (G.5.3), (G.5.4), (G.5.5), (G.5.6), (G.5.7), (G.5.8), (G.5.9), (G.5.10), and (G.5.11); particularly selected from (G.3.1), (G.5.1), and (G.5.3).

[0362] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group H), more preferably from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9), and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9), and (H.4.10).

[0363] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group I), more preferably from compounds (I.2.2) and (I.2.5).

[0364] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group J), more preferably from compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); especially (J.1.5).

[0365] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from component K), more preferably from compounds (K.1.41), (K.1.42), (K.1.44), (K.1.47), (K.1.57), (K.1.58), and (K.1.59); particularly selected from (K.1.41), (K.1.44), (K.1.47), (K.1.57), (K.1.58), and (K.1.59).

[0366] Any of the above mixtures preferably includes compound I as component 1), which is explicitly disclosed herein (e.g., in the table), and even more preferably selected from the list of compounds I.1-A-1 to I.1-A-937, compounds I.2-A-1 to I.2-A-937, compounds I.3-A-1 to I.3-A-937, and example compounds 1 to 464.

[0367] Biopesticides from groups L1) and / or L2) may also possess insecticidal, acaricidal, molluscicidal, pheromone-based, nematicidal, plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities. Biopesticides from groups L3) and / or L4) may also possess fungicidal, bactericidal, virucidal, plant defense activator, plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities. Biopesticides from group L5) may also possess fungicidal, bactericidal, virucidal, plant defense activator, insecticidal, acaricidal, molluscicidal, pheromone-based, and / or nematicidal activities.

[0368] Microbial agents that kill pests, particularly those from groups L1), L3), and L5), include not only pure cultures of the corresponding microorganisms as defined herein, but also cell-free extracts thereof, suspensions thereof in whole broth cultures and metabolite-containing media, or purified metabolites obtained from whole broth cultures of microorganisms.

[0369] Many of these biocides are deposited using the accession numbers mentioned in this article (prefixes such as ATCC or DSM refer to the acronyms for the corresponding culture deposits; see here for details, for example: http: / / www.wfcc.info / ccinfo / collection / by_acronym / The following strains are mentioned in the literature, registered and / or commercially available: a mixture of *Brucea buddinga* DSM14940 and DSM 14941 isolated in Constance, Germany in 1989 (e.g., budding spores, from bio-ferm GmbH, Austria, BlossomProtect®); *Azotoxinus brasiliensis* Sp245 originally isolated in the wheat region of southern Brazil (Pazufontu) at least before 1980 (BR 11005; e.g., from BASF Agricultural Specialties Ltd., Brazil, GELFIX® Gramíneas); *Azotoxinus brasiliensis* strains Ab-V5 and Ab-V6 (e.g., from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil). AzoMax from Brazil or Simbiose-Maíz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US ​​8,445,255); Bacillus amyloliquefaciens subsp. plantarum strain, previously sometimes referred to as Bacillus subtilis, recently classified as Bacillus berleisei along with Bacillus methylotrophicus and Bacillus berleisei (Int. J. Syst. Evol. Microbiol. [International Journal of Systematic and Evolutionary Microbiology] 66, 1212–1217, 2016): Bacillus amyloliquefaciens subsp. plantarum or Bacillus berleisei D747 (US 20130236522) isolated from the air in Kikukawa City, Japan. A1; FERM BP-8234; e.g., Double Nickel™ 55 WDG from Certis LLC, USA), *Bacillus amyloliquefaciens* subsp. plantae or *Bacillus belesiensis* FZB24 (also known as SB3615; DSM 96-2; J. Plant Dis. Prot. [Journal of Plant Diseases and Control] 105, 181-197, 1998; e.g., Taegro® from Novozyme Biologicals, Inc., USA), *Bacillus amyloliquefaciens* subsp. plantae or *Bacillus belesiensis* FZB42 (DSM 23117 ...Prot. [Journal of Plant Diseases and Control] 105, 181-197, 1998; e.g., RhizoVital® 42 from AbiTEP GmbH, Germany), *Bacillus plantarum* subsp. *amyllotherae* or *Bacillus belysium* MBI600 (also known as 1430; NRRL B-50595; US 2012 / 0149571 A1; e.g., Integral® from BASF Corp., USA), *Bacillus plantarum* subsp. *amyllotherae* or *Bacillus belysium* QST-713 (NRRL B-21661; e.g., Serenade® MAX from Bayer Crop Science LP, USA), *Bacillus plantarum* subsp. *amyllotherae* or *Bacillus belysium* QST-713 (NRRL B-21661; e.g., Serenade® MAX from Bayer Crop Science LP, USA), *Bacillus plantarum*, ... *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belesii* TJ1000 (also known as 1BE; ATCC BAA-390; CA 2471555 A1; e.g., QuickRoots™ from TJ Technologies, Watertown, SD, USA, USA); *Bacillus sturdier* CNCM I-1582, a variant of parent strain EIP-N1 isolated from soil in the Central Plains of Israel (CNCM I-1556) (WO 2009 / 126473, US 6,406,690; e.g., Votivo® from Bayer Crop Science, LLC, USA); *Bacillus pumilus* GHA180 isolated from the rhizosphere of apple trees in Mexico (IDAC 260707-01; e.g., PRO-MIX® from Premier Horticulture, Quebec, Canada, Canada). B. pumilus INR-7, also known as BU-F22 and BU-F33, was isolated from cucumbers infected with Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255) at least before 1993. B. pumilus KFP9F was isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; for example, from BASF Agricultural Specialities (Pty) Ltd., South Africa).Bac-UP or FUSION-P from South Africa), Bacillus pumilus QST 2808 was isolated in 1998 from soil collected in Pohnpei, Federated States of Micronesia (NRRL B-30087; e.g., Sonata® or Ballad® Plus from Bayer Crop Science LLC), Bacillus simplex ABU 288 (NRRL B-50304; US 8,445,255), also known as UD 1022 or UD10-22, and Bacillus subtilis FB17 were isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. [Systems and Applied Microbiology] 27, 372-379, 2004; US 2010 / 0260735; WO 2011 / 109395); Bacillus thuringiensis subsp. tsuriae ABTS-1857 was isolated in 1987 from soil taken from Ephraim lawns in Wisconsin, USA (also known as ABG-6346; ATCC SD-1372; e.g., XenTari® from BioFa AG, Münsingen, Germany); Bacillus thuringiensis subsp. kurstak ABTS-351 is equivalent to HD-1 isolated in 1967 from diseased bollworm larvae in Brownsville, Texas, USA (ATCC SD-1275; e.g., Dipel® DF from Valent BioSciences, IL, USA); Bacillus thuringiensis subsp. kurstak SB4 was isolated from the cadavers of African stem borer (E. saccharina) larvae (NRRL). B-50753; e.g., Beta Pro® from BASF Agriproducts Ltd., South Africa), Bacillus thuringiensis subsp. *Bacillus* NB-176-1, a mutant of strain NB-125, a wild-type strain isolated in 1982 from the dead pupae of the mealworm (DSM 5480; EP 585 215 B1; e.g., Novodor® from ValentBioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g., BotaniGard® 22WGP from Laverlam Int. Corp., USA), Beauveria bassiana JW-1 (ATCC 74040; e.g., CBC (Europe) Srl.Naturalis® (Italy), Beauveria bassiana PPRI 5339 was isolated from the larvae of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. BroadBand® from BASF Agricultural Specialties Ltd., South Africa), SEMIA 5019 (also known as 29W) strain of SEMIA 587 was isolated in Rio de Janeiro, Brazil and in 1967 in the State of Rio Grande do Sul, from areas previously inoculated with North American isolates and used as commercial inoculum since 1968 (Appl. Environ. Microbiol. [Applied and Environmental Microbiology] 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), and Soybean Slow Rhizobium 532c was isolated from a field in Wisconsin, USA (Nitragin 61A152; Can. J.). Plant. Sci. [Canadian Journal of Plant Science] 70, 661-666, 1990; e.g. Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), strain USDA 138 of soybean slow-growing rhizobium E-109 variant (INTA E109, SEMIA 5085; Eur. J. Soil Biol. [European Journal of Soil Biology] 45, 28-35, 2009; Biol. Fertil. Soils [Soil Biology and Fertility] 47, 81–89, 2011); by Appl. Environ. Microbiol.[Applied and Environmental Microbiology] 73(8), 2635, 2007 Known soybean slow-growing rhizobium strains preserved in SEMIA: SEMIA 5079 was isolated from soil by the Brazilian Institute of Agricultural Research in Cerrados (Embrapa-Cerrados) in the Cerrados region of Brazil and has been used as a commercial inoculum since 1992 (CPAC 15; e.g., GELFIX 5 or ADHERE 60 from BASF Agroproducts, Brazil); SEMIA 5080, a soybean slow-growing rhizobium obtained in Brazil by Embrapa-Cerrados under laboratory conditions and has been used as a commercial inoculum since 1992, is a natural variant (CB1809) of SEMIA 586 originally isolated in the United States (CPAC 7; e.g., GELFIX 5 or ADHERE from BASF Agroproducts, Brazil). 60); Burkholderia species A396 was isolated from soil in Nikko, Japan in 2008 (NRRLB-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA); Shield-shaped mold CON / M / 91-08 was isolated from rapeseed (WO 1996 / 021358; DSM 9660; e.g., Contans® WG, Intercept® WG from Bayer CropScience AG, Germany); hypersensitive protein (α-β) protein (Science 257, 85-88, 1992; e.g., Messenger™ or HARP-N-Tek from PlantHealth Care plc, UK); HearNPV (J. Invertebrate Pathol. 107, 2008). 112-126, 2011; for example, Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; and AgBiTech Pty Ltd from Queensland, Australia.Vivus® Max from Queensland, Australia), corn noctuid moth monocotyledon nucleopolyhedrovirus (HzSNPV) (e.g., Gemstar® from Cernan LLC, USA), corn noctuid moth nucleopolyhedrovirus ABA-NPV-U (e.g., Heligen® from AgroBiotech Ltd, Queensland, Australia), Hemibarbus hygrophilus (e.g., Nemasys® G from BASF Agricultural Specialities Limited, UK), Apopka-97 of *Metasequoia glyptostroboides* isolated from mealybugs on *Apis purpurea* in Apopka, Florida, USA (ATCC 20874; Biocontrol Science Technol. [Biological Control Science and Technology] 22(7), 747-761, 2012; e.g., PFR-97™ or PreFeRal® from Cernan LLC, USA), also known as 275 or V275, *Metarhizium anisopliae* microsporum variant F52 isolated from codling moth in Austria (DSM) 3884, ATCC90448; e.g., Met52®, Novozymes BiologicalsBioAg Group, Canada); *Megasteria burmannii* 277 isolated from grapes in central Israel (US 6,994,849; NRRL Y-30752; e.g., previously from Agrogreen Israel's Shemer®); *Paecilomyces lilacinus* 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO 1991 / 02051; Crop Protection 27, 352-361, 2008; e.g., from Bayer Crop Science AG's BioAct® and from CeraCon®, USA); *Bacillus nasus* NAS6G6 isolated from grass rhizosphere in South Africa at least before 2008 (WO2014 / 029697; NRRL). B-50755; for example, from BASF Agricultural Specialities (Pty) Ltd., South Africa.Bacillus strains isolated from soil samples from various European regions, including Germany (BAC-UP): Epiphytic Bacillus Lu17015 (WO 2016 / 020371; DSM 26971), Polymyxin Bacillus plantarum Lu16774 (WO 2016 / 020371; DSM 26969), Polymyxin Bacillus plantarum strain Lu17007 (WO2016 / 020371; DSM 26970); Pasteurella multocida Pn1 was isolated from a soybean field in Illinois, USA in the mid-2000s (ATCC SD-5833; Federal Register [Federal Register] 76(22), 5808, February 2, 2011; Clariva™ PN from Syngenta Crop Protection, LLC, for example, Penicillium baicalensis (also known as P. baicalensis). The strains *Bilaii* ATCC 18309 (= ATCC 74319), ATCC 20851, and / or ATCC22348 (= ATCC 74318) were originally isolated from soil in Alberta, Canada (Fertilizer Research, 39, 97-103, 1994; Can. J. Plant Sci., 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump Start®, Provide® from Novozymes BioAgriculture Group, Canada), Polygonum cuspidatum extract (EP 0307510 B1; e.g. Regalia® from Marrone BioInnovations, Davis, CA, USA). Milsana® (SC or from Bayer AG, Germany), Small leafroller nematode (e.g., Millenium® from BASF Agriproducts Ltd., UK), and Noctuid moth nematode (e.g., from BioWorks, Inc., USA).Nemashield® (from BASF Agriproducts Ltd., USA); Nemasys® (from BASF Agriproducts Ltd., UK); *Streptomyces flavus* NRRL B-50550 (WO 2014 / 124369; Bayer Crop Science, Germany); *Trichoderma hygroscopicum* JM41R isolated in South Africa (NRRL 50759; also known as *Trichoderma apicals*; e.g., Trichoplus® from BASF Agriproducts Ltd., South Africa); *Trichoderma harzianum* T-22 also known as KRL-AG2 (ATCC 20847; BioControl [Biological Control] 57, 687-696, 2012; e.g., Plantshield® from American Bioengineering Company or SabrEx™ from Advanced Biological Marketing Inc., VanWert, OH, USA).

[0370] According to another embodiment of the mixture, at least one biocidal agent II is selected from groups L1 to L5:

[0371] L1) Microbial agents with antifungal, antibacterial, antiviral, and / or plant defense activator activities: *Bacillus buddingus* DSM 14940 and DSM 14941 (L1.1), *Bacillus amyloliquefaciens* AP-188 (L1.2), *Bacillus amyloliquefaciens* subsp. *plantarea* D747 (L1.3), *Bacillus amyloliquefaciens* subsp. *plantarea* FZB24 (L1.4), *Bacillus amyloliquefaciens* subsp. *plantarea* FZB42 (L1.5), *Bacillus amyloliquefaciens* subsp. *plantarea* MBI600 (L1.6), *Bacillus amyloliquefaciens* subsp. *plantarea* QST-713 (L1.7), *Bacillus amyloliquefaciens* subsp. *plantarea* TJ1000 (L1.8), *Bacillus pumilus* GB34 (L1.9), *Bacillus pumilus* GHA 180 (L1.10), *Bacillus pumilus* INR-7 (L.1.11), Bacillus pumilus KFP9F (L.1.12), Bacillus pumilus QST 2808 (L.1.13), Bacillus simplex ABU 288 (L.1.14), Bacillus subtilis FB17 (L.1.15), *Scutellaria baicalensis* CON / M / 91-08 (L.1.16), *Saccharomyces cerevisiae* NRRL Y-30752 (L.1.17), *Bacillus vesicularis* NAS6G6 (L.1.18), *Bacillus epiphyticus* Lu17015 (L.1.25), *Bacillus polymyxa* subsp. *plantare* Lu16774 (L.1.26), *Bacillus polymyxa* subsp. *plantare* strain Lu17007 (L.1.27), *Penicillium baicalensis* ATCC 22348 (L.1.19), *Penicillium baicalensis* ATCC 20851 (L.1.20), Penicillium baicalensis ATCC 18309 (L.1.21), Streptomyces flavus NRRL B-50550 (L.1.22), Trichoderma hydathodes JM41R (L.1.23), Trichoderma harzianum T-22 (L.1.24);

[0372] L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activities: hypersensitive protein (L.2.1), Polygonum cuspidatum extract (L.2.2);

[0373] L3) Microbial biocides with insecticidal, acaricidal, snailicidal, and / or nematicidal activities: Bacillus thuringiensis I-1582 (L.3.1); Bacillus thuringiensis subsp. niger ABTS-1857 (L.3.2), Bacillus thuringiensis subsp. Kurstak ABTS-351 (L.3.3), Bacillus thuringiensis subsp. Kurstak SB4 (L.3.4), Bacillus thuringiensis subsp. *Stromboides* NB-176-1 (L.3.5), Beauveria bassiana GHA (L.3.6), Beauveria bassiana JW-1 (L.3.7), Beauveria bassiana PPRI 5339 (L.3.8), Burkholderia species A396 (L.3.9), HearNPV (cotton bollworm nucleopolyhedrovirus) (L.3.10), HzNPV ABA-NPV-U (corn noctuid moth nucleopolyhedrovirus) (L.3.11), HzSNPV (corn noctuid moth monocotyledon nucleopolyhedrovirus) (L.3.12), Heterohabditis bacteriophora (L.3.13), Apopka-97 (L.3.14), Microsporum variegatum F52 (scarlet beetle), Paecilomyces lilacinus 251 (L.3.16), Pasteurella multocida Pn1 (L.3.17), Small leafroller nematode (L.3.18), Small noctuid moth nematode (L.3.19);

[0374] L4) Biochemical pest control agents with insecticidal, acaricidal, snailic, pheromone-based and / or nematicidal activities: cis-jasmone (L.4.1), methyl jasmone (L.4.2), and soap extract (L.4.3);

[0375] L5) Microbial pest control agents with plant stress reduction, plant growth regulator, plant growth promotion and / or yield enhancement activities: *Azotobacter brasiliensis* Ab-V5 and Ab-V6 (L.5.1), *Azotobacter brasiliensis* Sp245 (L.5.2), *S. japonicum* SEMIA 587 (L.5.3), *S. japonicum* SEMIA 5019 (L.5.4), *B. japonicum* 532c (L.5.5), *B. japonicum* E-109 (L.5.6), *B. japonicum* SEMIA5079 (L.5.7), *B. japonicum* SEMIA 5080 (L.5.8).

[0376] Furthermore, the present invention relates to agricultural chemical compositions comprising a mixture of at least one compound I (component 1) and at least one biocide selected from group L) (component 2), particularly at least one biocide selected from groups L1) and L2) as described above, and (if necessary) at least one suitable adjuvant.

[0377] Furthermore, the present invention relates to agricultural chemical compositions comprising a mixture of at least one compound I (component 1) and at least one biocide selected from group L) (component 2), particularly at least one biocide selected from groups L3) and L4) as described above, and (if necessary) at least one suitable adjuvant.

[0378] Also preferred is a mixture comprising a biocide as biocide II (component 2), the biocide being selected from groups L1), L3), and L5), preferably selected from those indicated above as (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), and (L.1.19). , (L.1.20), (L.1.21), (L.1.25), (L.1.26), (L.1.27), (L.3.1); (L.3.9), (L.3.16), (L.3 .17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2) The strains are selected from (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1). These mixtures are particularly suitable for treating propagating material, i.e., for seed treatment purposes, and are equally suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, maize, and legumes such as soybeans.

[0379] Also preferred is a mixture comprising a biocide as biocide II (component 2), the biocide being selected from groups L1 and L3. And L5), preferably selected from (L1.1), (L.1.2), (L.1.3), (L.1.6), (L.1.7), (L.1.9), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1.26), (L.1.27), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3... (L.3.10), (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2) strains, even more preferably selected from (L.1.2), (L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.15) and (L.4.2). These mixtures are particularly suitable for foliar treatment of cultivated plants, especially vegetables, fruits, vines, grains, corn, and legumes such as soybeans.

[0380] Compositions containing mixtures of active ingredients can be prepared by common means, such as those given for compositions of compound I.

[0381] When live microorganisms, such as biocides II from groups L1), L3), and L5), form part of a composition, such compositions can be prepared by common means (e.g., HD Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO 2008 / 002371, US 6,955,912, US 5,422,107).

[0382] Example

[0383] Synthesis method

[0384] Example-1Synthesis of methyl (2E)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-(2,4,6-trifluorophenyl)ethylidene]amino]oxymethyl]-3-methyl-phenyl]acetate (compound number 2)

[0385] Step 1: 2-Methoxy-(Z)-1-(2,4,6-trifluorophenyl)ethyl ketone oxime

[0386] Diisopropylamine (16.85 g, 0.17 mol) in 100 mL THF was cooled to 0°C. 60 mL of n-butyllithium solution (2.5 M, in heptane, 0.15 mol) was added dropwise, maintaining the temperature at 0°C. The reaction was further stirred for 15 min and then cooled to -78°C. 1,3,5-trifluorobenzene (20 g, 0.15 mol) in 50 mL THF was added to the reaction mixture over a 30 min period. The reaction was stirred at -78°C for 1 h. N,2-dimethoxy-N-methylacetamide (24.19 g, 0.18 mol) in 50 mL THF was added dropwise over 1 hour at -78°C. The reaction was stirred at the same temperature for 1 h and quenched with 200 mL of 1 N HCl aqueous solution. The organic layer was separated, and the aqueous layer was washed with 200 mL of methyl tert-butyl ether (MTBE). The organic layers were combined and washed with brine, dried over sodium sulfate, and concentrated under vacuum to give 18 g of crude 2-methoxy-1-(2,4,6-trifluorophenyl)ethyl ketone. The crude substance was dissolved in 230 mL of methanol and 13.9 g (0.17 mol) of sodium acetate and 11.7 g (0.17 mol) of hydroxylamine hydrochloride were added. The mixture was heated to 50°C and stirred for 2 hours. The reaction was cooled to RT and the solvent was evaporated under vacuum to about 100 mL. The residue was diluted with 200 mL of water and extracted with dichloromethane (DCM, 100 mL × 2). The organic layers were combined and washed with brine (2 × 30 mL), dried over sodium sulfate, and concentrated under vacuum. The crude substance obtained was purified by column chromatography to give 10 g of 2-methoxy-(Z)-1-(2,4,6-trifluorophenyl)ethyl ketone oxime. Yield: 30%. 1 H NMR (500 MHz, DMSO-d6) δ = 11.93 (s, 1H), 7.34 – 7.18 (m, 2H), 4.45 (s, 2H), 3.18 (s, 3H).

[0387] Step 2:(2E)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-(2,4,6-trifluorophenyl)ethylene]-amino]oxymethyl]-3-methyl-phenyl]acetate (Compound No. 2)

[0388] Cs₂CO₃ (10.42 g, 31.98 mmol) was added to a solution of (2E)-2-[2-(bromomethyl)-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (4.8 g, 15.99 mmol) in acetonitrile (AcN, 40 mL) and stirred at RT for 10 min. Then, 2-methoxy-(Z)-1-(2,4,6-trifluorophenyl)acetone oxime (3.54 g, 16.15 mmol) was added to 10 mL of AcN and stirred at RT for 16 h. The reaction was monitored by TLC (heptane:ethyl acetate (EtAc) = 5:1) and indicated as complete. The reactants were quenched with water (48 mL, 10 volumes). The reactants were extracted with MTBE (10 volumes × 3). The organic layers were mixed, dried over sodium sulfate, concentrated (9 g), and purified by column chromatography to give the title compound (6 g, yield 85.57%). 1 H NMR (500 MHz, DMSO-d6) δ 7.36 – 7.23 (m, 4H), 7.03 (dd, J = 7.3,1.8 Hz, 1H), 5.00 (s, 2H), 4.33 (s, 2H), 3.92 (s, 3H), 3.66 (s, 3H), 3.15 (s,3H), 2.40 (s,3H).

[0389] Example 2: Synthesis of (2E)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-(2,4,6-trifluorophenyl)ethylidene]amino]oxymethyl]-3-methyl-phenyl]-N-methyl-acetamide (compound number 1)

[0390] Methylamine (6.69 g, 86.223 mmol; 36 mL of 40% MeNH2 in H2O) was added to a solution of (2E)-2-methoxyimino-2-[2-[[(Z)-[2-methoxy-1-(2,4,6-trifluorophenyl)ethylene]amino]oxymethyl]-3-methyl-phenyl]acetate (Example-1) (12.6 g, 28.741 mmol) in THF (60 mL). The reaction mixture was stirred at RT for 1 h. The reaction was monitored by TLC (50% heptane in EtAc). After completion, the reaction was quenched with cold water (100 mL). The precipitated solid was filtered, washed with water (50 mL), and dried under vacuum to give 10.5 g of the title compound as a colorless solid (yield: 80.13%). 1 H NMR (300 MHz, DMSO-d6) δ 8.19 (d, J = 4.9 Hz, 1H), 7.36 –7.22 (m, 4H), 6.96 (dd, J = 6.9, 2.1 Hz, 1H), 5.01 (s, 2H), 4.34 (s, 2H), 3.86 (s, 3H), 3.14 (s, 3H), 2.67 (d, J = 4.7 Hz, 3H), 2.39 (s, 3H).

[0391] Example 3: Synthesis of (E)-3-methoxy-2-[2-[[(Z)-[2-methoxy-1-(2,4,6-trifluorophenyl)ethylene]amino]oxymethyl]-3-methyl-phenyl]prop-2-enoic acid methyl ester (compound number 4)

[0392] A solution of (E)-2-[2-(bromomethyl)-3-methyl-phenyl]-3-methoxy-prop-2-enoate (20.05 g, 68.52 mmol) in AcN (150 mL), Cs₂CO₃ (44.65 g, 137.05 mmol), and 2-methoxy-(Z)-1-(2,4,6-trifluorophenyl)ethyl ketone oxime (15.16 g, 69.21 mmol) were stirred at RT for 16 h. The reaction mixture was filtered, and the filtrate was concentrated under vacuum. The obtained crude substance was purified by column chromatography to give the title compound (21 g, 67.25% yield). 1H NMR(300 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.36 – 7.21 (m, 3H), 7.18 (dd, J = 7.8,6.2 Hz, 1H), 6.97 – 6.88 (m, 1H), 5.04 (s, 2H), 4.32 (s, 2H), 3.77 (s, 3H), 3.33 (s, 3H), 3.14 (s, 3H), 2.38 (s, 3H).

[0393] Example 4: Synthesis of (2E)-2-[2-[[(Z)-[1-(3,4-difluorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (compound number 5)

[0394] Step-1 (Z)-1-(3,4-difluorophenyl)-2-methoxy-ethyl ketone oxime

[0395] Mg scrap (3.46 g, 142.29 mmol) was heated to 50°C in 100 mL of THF. 4-Bromo-1,2-difluorobenzene (25 g, 129.54 mmol) dissolved in 10 mL of THF was added over a 10 min period. The reaction mixture was stirred at 50°C for 90 min and then cooled to 0°C. Methoxyacetonitrile (10.12 mL, 142.49 mmol) in 10 mL of THF was added to the reaction mixture over a 17 min period, and then cooled to 5°C. The reaction mixture was stirred at the same temperature for 2 h 28 min, quenched with 150 mL of 2 M HCl aqueous solution, and extracted with EtAc (150 mL × 2). The organic layers were combined, washed with brine, dried over Na₂SO₄, and concentrated under vacuum to give 14.72 g of crude 1-(3,4-difluorophenyl)-2-methoxy-ethyl ketone.

[0396] 1-(3,4-difluorophenyl)-2-methoxy-ethyl ketone (3 g, 16.11 mmol) was dissolved in 50 mL of methanol, and sodium acetate (2.02 g, 24.17 mmol) and hydroxylamine hydrochloride (1.73 g, 24.17 mmol) were added. The mixture was heated to 50°C and stirred for 17 h. The reaction was cooled to RT, and the solvent was evaporated under vacuum to half its volume. The remainder was diluted with 15 mL of water and extracted with DCM (15 mL × 3). The organic layers were combined and washed with brine (2 × 15 mL), dried over Na₂SO₄, and concentrated under vacuum. The crude product was purified by column chromatography to give 1.17 g of (Z)-1-(3,4-difluorophenyl)-2-methoxy-ethyl ketone oxime. Yield: 36.09%. 1 ¹H NMR (500 MHz, acetone-d6) δ = 7.68 – 7.61 (m, 1H), 7.59 – 7.52 (m, 1H), 7.32 – 7.25 (m, 1H), 4.68 – 4.62 (s, 2H), 3.32 – 3.28 (s, 3H).

[0397] Step 2: (2E)-2-[2-[[(Z)-[1-(3,4-difluorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester

[0398] Cs₂CO₃ (10.25 g, 31.46 mmol) was added to a solution of (Z)-1-(3,4-difluorophenyl)-2-methoxy-ethyl oxime (4.22 g, 20.97 mmol) in AcN (50 mL) and stirred at RT for 5 min. Then, methyl (2E)-2-[2-(bromomethyl)-3-methyl-phenyl]-2-methoxyimino-acetate (6.92 g, 23.07 mmol) was added and stirred at RT for 17 h. The reaction mixture was quenched with water (21 mL) and extracted with EtAc (15 mL × 3). The organic layers were combined, washed with brine (15 mL × 1), dried over sodium sulfate, concentrated under vacuum, and purified by column chromatography. (2E)-2-[2-[[(Z)-[1-(3,4-difluorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (7.2 g, yield 81.72%) was obtained as a white solid. 1H NMR (400 MHz, MeOD) δ 7.58 - 7.51 (m,1H), 7.49 - 7.41 (m, 1H), 7.31 - 7.18 (m, 3H), 7.02 - 6.91 (m, 1H), 5.22-5.01 (s, 2H), 4.52-4.48 (s, 2 H), 3.97-3.92 (s, 3 H), 3.72 - 3.69 (s, 3H), 3.28 - 3.21 (s, 3H), 2.48 - 2.42 (s, 3 H).

[0399] Step 3: (2E)-2-[2-[[(Z)-[1-(3,4-difluorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (Compound No. 5)

[0400] Methylamine (5.2 g, 67.07 mmol; 40% MeNH2 in H2O) was added to a solution of (2E)-2-[2-[[(Z)-[1-(3,4-difluorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (9.4 g, 22.35 mmol) in THF (50 mL). The reaction mixture was stirred at RT for 22 h. The reaction mixture was concentrated under vacuum, ground with heptane, filtered, and dried to give 7.69 g of the title compound as a beige solid (yield = 73.8%). 1 H NMR (400 MHz, CDCl3) δ 7.6 - 7.5 (m,1H), 7.4 - 7.35 (m, 1H), 7.31 -7.05 (m, 4H), 6.8 - 6.76 (s 1H), 5.22- 5.01 (s, 2H), 4.52-4.48 (s, 2 H), 3.97-3.92 (s, 3 H), 3.35 – 3.21 (s, 3H), 2.91 – 2.82 (d, 3 H), 2.48 – 2.42 (s, 3 H).

[0401] Example 5: Synthesis of (E)-2-[2-[[(Z)-[1-(2,4-dichlorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-3-methoxy-prop-2-enoic acid methyl ester (compound number 6)

[0402] Step-1:(Z)-1-(2,4-dichlorophenyl)-2-methoxy-ethyl oxime

[0403] The solution of 2,4-dichloro-1-iodobenzene (10.0 g, 36.67 mmol) in 50 mL of THF was cooled to 0°C. A solution of isopropyl magnesium chloride in THF (22 mL, 44 mmol) was added dropwise, maintaining the temperature at 0°C. The reaction was stirred for another 1 h. A solution of N,2-dimethoxy-N-methylacetamide (5.86 g, 44 mmol) in 20 mL of THF was added dropwise over 30 min. The reaction was stirred for another 1 h at 0°C. The reaction was quenched with 50 mL of 1 N HCl aqueous solution. The organic layer was separated, and the aqueous layer was washed with 50 mL of MTBE. The organic layers were combined, washed with brine, dried over Na₂SO₄, and concentrated under vacuum to give 9.0 g of crude 1-(2,4-dichlorophenyl)-2-methoxy-acetone. The crude substance was dissolved in 90 mL of methanol and 3.2 g (82.18 mmol) of NaOH and 4.2 g (61.63 mmol) of hydroxylamine hydrochloride were added to 18 mL of water. The mixture was heated to 50°C and stirred for 2 h. The reaction was cooled to RT and diluted with 200 mL of water and extracted with DCM (100 mL × 2). The organic layers were combined and washed with brine (2 × 30 mL), dried over Na2SO4, and concentrated under vacuum. The crude substance obtained was purified by column chromatography to give 4.35 g of (Z)-1-(2,4-dichlorophenyl)-2-methoxy-acetone oxime. Yield: 40.7%. 1 H NMR(300 MHz, DMSO-d6) δ 11.68 (s, 1H), 7.65 (d, J = 1.9 Hz, 1H), 7.53 – 7.37 (m,2H), 4.52 (s, 2H), 3.16 (s, 3H).

[0404] Step 2: (E)-2-[2-[[(Z)-[1-(2,4-dichlorophenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-3-methoxy-prop-2-enoic acid methyl ester (compound number 6)

[0405] Cs₂CO₃ (30.6 g, 94.05 mmol) was added to a solution of (E)-2-[2-(bromomethyl)-3-methyl-phenyl]-3-methoxy-prop-2-enoate (14.06 g, 47.02 mmol) in AcN (90 mL), and the mixture was stirred at RT for 10 min. (Z)-1-(2,4-dichlorophenyl)-2-methoxy-ethyl ketone oxime (11.0 g, 47.02 mmol) was added to 20 mL AcN, and the reaction was stirred at RT for 16 h. The reaction was monitored by TLC (20% EtAc in heptane). After completion, the reactants were quenched with water (48 mL) and extracted with MTBER (30 mL × 3). The organic layers were mixed, dried over sodium sulfate, concentrated under vacuum, and purified by column chromatography to give the title compound (15.9 g, 85.57% yield). 1 H NMR (300 MHz, DMSO-d6) δ7.74 – 7.58 (m, 2H), 7.47 (m, 1H), 7.42 – 7.31 (m, 1H), 7.30 – 7.10 (m, 2H), 6.99 – 6.88 (m, 1H), 5.04 (s, 2H), 4.41 (s, 2H), 3.78 (d, J = 0.8 Hz, 3H), 3.57 (d, J = 0.8 Hz, 3H), 3.12 (d, J = 0.8 Hz, 3H), 2.40 (s, 3H).

[0406] Example 6: Synthesis of (2E)-2-[2-[[(Z)-[1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (compound 7)

[0407] Step-1: (Z)-1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethyl ketone oxime

[0408] Diisopropylamine (9.13 g, 90.20 mmol) in 80 mL THF was cooled to 0°C. 33.3 mL of n-butyllithium solution (2.5 M, in heptane, 83.26 mmol) was added dropwise, maintaining the temperature at 0°C. The reaction was further stirred for 15 min and then cooled to -78°C. 1,3-Difluoro-5-methoxy-benzene (10 g, 69.4 mmol) in 20 mL THF was added to the reaction mixture over a 30 min period. The reaction was stirred at -78°C for 1 h. N,2-Dimethoxy-N-methylacetamide (11.1 g, 83.26 mmol) in 20 mL THF was added dropwise over 1 h at -78°C. The reaction was stirred for 1 h and quenched with 100 mL of 1 N HCl aqueous solution. The organic layer was separated, and the aqueous layer was washed with 100 mL of MTBE. The organic layers were combined and washed with brine, dried over Na₂SO₄, concentrated under vacuum, and purified by column chromatography to give 1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethyl ketone. The obtained 1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethyl ketone (10 g, 43.26 mmol) was dissolved in 80 mL of methanol, and 3.71 g (92.52 mmol) of NaOH and 4.82 g (69.38 mmol) of hydroxylamine hydrochloride were added to 20 mL of water. The mixture was heated to 50°C and stirred for 2 h. The reaction was cooled to RT, diluted with 200 mL of water, and extracted with DCM (100 mL × 2). The organic layers were combined and washed with brine (2 × 30 mL), dried over Na₂SO₄, and concentrated under vacuum. The crude substance obtained was purified by column chromatography to give 8.12 g of (Z)-1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethyl oxime. Yield: 51%. 1 H NMR (500 MHz, DMSO-d6) δ= 11.73 (s, 1H), 6.80 – 6.68 (m, 2H), 4.42 (s, 2H), 3.81 (s, 3H), 3.17 (s, 3H).

[0409] Step 2: (2E)-2-[2-[[(Z)-[1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester

[0410] Cs₂CO₃ (22.55 g, 69.20 mmol) and (Z)-1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethyl oxime (8 g, 36.60 mmol) were added to a solution of (2E)-2-[2-(bromomethyl)-3-methyl-phenyl]-2-methoxy-imino-acetate (10.91 g, 66.33 mmol) in DMF (60 mL). The reaction mixture was stirred at 40°C for 2.5 h. The reaction was monitored by TLC (20% EtAc in heptane). After completion, the reaction was quenched with 150 mL of water (150 mL) and extracted with EtAc (30 mL × 3). The organic layers were combined, dried over sodium sulfate, and concentrated. The crude mixture was purified by column chromatography to obtain methyl (2E)-2-[2-[[(Z)-[1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethylene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid (13.4 g, yield 81.68%). 1 H NMR (500MHz, DMSO-d6) δ 7.35 – 7.27 (m, 2H), 7.05 – 7.00 (m, 1H), 6.84 – 6.73 (m,2H), 4.97 (s, 2H), 4.30 (s, 2H), 3.92 (s, 3H), 3.81 (s, 3H), 3.67 (s, 3H), 3.13 (s, 3H), 2.40 (s, 3H).

[0411] Step 3: (2E)-2-[2-[[(Z)-[1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (Compound No. 7)

[0412] A solution of (2E)-2-[2-[[(Z)-[1-(2,6-difluoro-4-methoxy-phenyl)-2-methoxy-ethylene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (7.0 g, 15.54 mmol) in THF (56 mL) was added to a solution of 40% methylamine aqueous solution (36.4 mL). The reaction mixture was stirred at RT for 1 h. The reaction was monitored by TLC (50% heptane in EtAc). After completion, the reaction mixture was quenched with cold water (100 mL) and extracted with EtAc (50 mL × 3). The organic layers were mixed, dried over sodium sulfate, and concentrated. The crude mixture was purified by column chromatography to give the title compound (6.5 g, 86.8% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.19 (q, J = 4.7 Hz, 1H), 7.34 – 7.23(m, 2H), 6.95 (dd, J = 7.4, 1.7 Hz, 1H), 6.84 – 6.74 (m, 2H), 4.99 (s, 2H), 4.31 (s, 2H), 3.86 (s, 3H), 3.81 (s, 3H), 3.12 (s, 3H), 2.67 (d, J = 4.8 Hz, 3H), 2.39 (s, 3H).

[0413] Table L: LCMS Method

[0414]

[0415] The LCMS method used in Table S is shown in the LCMS column.

[0416] Table S:

[0417]

[0418]

[0419] Biological research

[0420] Greenhouse research

[0421] The compound was dissolved in a mixture of acetone and / or dimethyl sulfoxide and an ethoxylated alkylphenol-based wetting / emulsifier, Wettol, at a solvent-emulsifier ratio (volume) of 99:1 to obtain a total volume of 5 ml. Water was then added to a total volume of 100 ml. This stock solution was then diluted with the solvent-emulsifier-water mixture to the final concentration given in the table below.

[0422] Example of application 1. Preventive fungicidal control of early blight (Alternaria alternata P1) on tomatoes.

[0423] Tomato seedlings were grown in pots. These plants were sprayed to drip rate with the aforementioned spray solution, which contained the active ingredients or mixtures mentioned in the table below at concentrations. The next day, the treated plants were inoculated with an aqueous suspension of *Alternaria alternata*. The strain used contained F129L, an amino acid substitute in the mitochondrial cytochrome b protein that conferred resistance to the Qo inhibitor. The test plants were then immediately transferred to a humidification chamber. After 5 days at 18°C ​​to 20°C and saturated relative humidity, the extent of fungal infection on the leaves was visually assessed as a percentage of diseased leaf area.

[0424] Example of application 2. Therapeutic control of soybean rust caused by PHAKPA K2 on soybeans.

[0425] The leaves of potted soybean seedlings were inoculated with spores of *Ipomoea spp.* rust. The strain used contained F129L, an amino acid substitute in the mitochondrial cytochrome b protein that conferred resistance to the Qo inhibitor. To ensure successful artificial inoculation, the plants were transferred to a humid chamber at approximately 95% relative humidity and 20°C to 24°C for 24 hours. The next day, the plants were incubated for one day in a greenhouse at 23°C–27°C and relative humidity between 60% and 80%. The plants were then sprayed to drip rate with the aforementioned spray solution containing the active ingredient or a mixture thereof at the concentrations described below. The plants were allowed to air dry. The test plants were then incubated in a greenhouse at 23°C–27°C and relative humidity between 60% and 80% for up to 14 days. The degree of fungal infection on the leaves was visually assessed as % of diseased leaf area.

[0426] Example of application 3. Protective control of soybean rust caused by the phytosporum prakpa P2 fungus on soybeans.

[0427] Spray the leaves of potted soybean seedlings with the aforementioned spray solution, containing the active ingredient or a mixture thereof at the concentrations described below, until dripping. Allow the plants to air dry. Incubate the test plants for 2 days in a greenhouse at 23°C–27°C and relative humidity between 60% and 80%. Then, inoculate the plants with spores of *Pseudomonas beanus* rust fungus. The strain used contains F129L, an amino acid substitution in the mitochondrial cytochrome b protein that confers resistance to Qo inhibitors. To ensure successful artificial inoculation, transfer the plants to a humid chamber at approximately 95% relative humidity and 20°C–24°C for 24 hours. Incubate the test plants for up to 14 days in a greenhouse at 23°C–27°C and relative humidity between 60% and 80%. Visually assess the extent of fungal infection on the leaves as a percentage of diseased leaf area; the disease level in the untreated control was typically above 85%.

[0428] Example of application 4. Protective control of soybean rust caused by the phytosporum prakpa (PHAKPA P6) on soybeans.

[0429] Spray the leaves of potted soybean seedlings with the aforementioned spray solution, containing the active ingredient at the concentrations described below, until dripping. Allow the plants to air dry. Incubate the test plants for six days in a greenhouse at 23°C–27°C and relative humidity between 60% and 80%. Then, inoculate the plants with spores of *Pseudomonas beanus* rust fungus. The strain used contains F129L, an amino acid substitution in the mitochondrial cytochrome b protein that confers resistance to Qo inhibitors. To ensure successful artificial inoculation, transfer the plants to a humid chamber at approximately 95% relative humidity and 23°C–27°C for 24 hours. Incubate the test plants in a greenhouse at 23°C–27°C and relative humidity between 60% and 80% for up to 14 days. Visually assess the extent of fungal infection on the leaves as a percentage of diseased leaf area; the disease level in the untreated control was typically above 85%.

[0430] Example of application 5. Protective control of soybean rust caused by PHAKPA P9.

[0431] Spray the leaves of potted soybean seedlings with the aforementioned spray solution until dripping. This spray solution contains the active ingredient or a mixture thereof at the concentrations described below. Allow the plants to air dry. Incubate the test plants in a greenhouse at 23°C–27°C and a relative humidity between 60% and 80% for 9 days. Then, inoculate the plants with spores of *Pseudomonas beanus* rust fungus. The strain used contains F129L, an amino acid substitute in the mitochondrial cytochrome b protein that confers resistance to Qo inhibitors. To ensure successful artificial inoculation, transfer the plants to a humid chamber at approximately 95% relative humidity and 20°C–24°C for 24 hours. Incubate the test plants in a greenhouse at 23°C–27°C and a relative humidity between 60% and 80% for up to 14 days. Visually assess the extent of fungal infection on the leaves as a percentage of diseased leaf area.

[0432] Example of application 6. Brown rust on wheat caused by *PUCCRT P7* (a type of rust fungus). Disease prevention and control

[0433] Spray the first two developing leaves of potted wheat seedlings with the aforementioned spray solution, containing the active ingredient or a mixture thereof at the concentrations described below, until dripping. Seven days later, sprinkle spores of *Strombus haematocephalus* onto the plants. To ensure successful artificial inoculation, transfer the plants to a dark, humid chamber with a relative humidity of 95% to 99% and a temperature of 20°C to 24°C for 24 hours. Then, incubate the test plants in a greenhouse at 20°C to 24°C and a relative humidity of 65% to 70% for 9 to 12 days. Visually assess the degree of fungal infection on the leaves as a percentage of diseased leaf area.

[0434] Example of application 7. Browning on wheat caused by *PUCCRT P10* (a type of rust fungus). Preventive treatment of rust

[0435] Spray the first two developing leaves of potted wheat seedlings with the aforementioned spray solution, containing the active ingredient or a mixture thereof at the concentrations described below, until dripping. Ten days later, inoculate the plants with spores of *Strombus haematocephalus*. To ensure successful artificial inoculation, transfer the plants to a dark, humid chamber with a relative humidity of 95% to 99% and a temperature of 20°C to 24°C for 24 hours. Then, incubate the test plants in a greenhouse at 20°C–24°C and a relative humidity of 65% to 70% for 6 days. Visually assess the extent of fungal infection on the leaves as a percentage of diseased leaf area.

[0436] Example of application 8. Corn on maize caused by Puccinia sorghi (PUCCSO P1). Protective control of rust

[0437] Spray the primary leaves of potted corn seedlings with the aforementioned spray solution, containing the active ingredient or a mixture thereof at the concentrations described below, until dripping. One day later, before harvest, sprinkle spores of *Sorghum stalk rust* onto the plants. To ensure successful artificial inoculation, transfer the plants to a dark, humid room with a relative humidity of approximately 55% to 70% and a temperature of 20°C to 24°C, and incubate them for approximately fourteen days. Visually assess the extent of fungal infection on the primary leaves as a percentage of diseased leaf area.

[0438] Example of application 9. Strand rust caused by *Puccinia striiformis* (PUCCST K4) on wheat. Therapeutic control of wheat stripe rust

[0439] The first two developing leaves of potted wheat seedlings were inoculated with spores of *Striga styracifolium*. To ensure successful artificial inoculation, the plants were transferred to a dark room at 5°C for 24 hours. The plants were then incubated for 3 days in a greenhouse at 16°C and a minimum relative humidity of 75%. The plants were sprayed to drip rate with the aforementioned spray solution containing the active ingredient or a mixture thereof at the concentrations described below. The plants were then allowed to air dry. The plants were then incubated for up to 12 days in a greenhouse at 16°C and a minimum relative humidity of 75%. The degree of fungal infection on the leaves was visually assessed as a percentage of diseased leaf area.

[0440] Example of application 10. Preventive treatment of wheat stripe rust caused by *PUCCST P7*. rule

[0441] The first two developing leaves of potted wheat seedlings were sprayed with the aforementioned spray solution, containing the active ingredient or a mixture thereof at the concentrations described below, until dripping. Seven days later, the plants were inoculated with spores of *Striga styracifolium*. To ensure successful artificial inoculation, the plants were transferred to a dark room at 5°C for 24 hours. The experimental plants were then cultured in a greenhouse at 16°C and a minimum relative humidity of 75% for up to 14 days. The degree of fungal infection on the leaves was visually assessed as a percentage of diseased leaf area.

[0442] Example of application 11. Control of net blotch disease on barley caused by Pyrnte P1.

[0443] The first fully developed leaf of the potted barley plant was sprayed with the aforementioned spray solution, containing the active ingredients or mixtures thereof at concentrations mentioned in the table below, until dripping. The next day, the treated plants were inoculated with an aqueous spore suspension of *Helicobacter pylori* (synonym: *Helicobacter pylori*). The strain used contained the F129L amino acid substitution in the mitochondrial cytochrome b protein, which confers resistance to the Qo inhibitor. The test plants were then incubated at 20°C–24°C and approximately 70% relative humidity for up to 19 days, and the degree of fungal invasion on the leaves was visually assessed as % of diseased leaf area.

[0444] Example of application 12. Control of net blotch disease on barley caused by Pyrnte P4.

[0445] Spray the first fully developed leaf of potted barley plants with the aforementioned spray solution, containing the active ingredients or mixtures thereof at concentrations mentioned in the table below, until dripping. Seven days later, inoculate the treated plants with an aqueous spore suspension of *Helicobacter pylori* (synonym: *Helicobacter pylori*). The strain used contains the F129L amino acid substitution in the mitochondrial cytochrome b protein, which confers resistance to the Qo inhibitor. After incubation at 20°C–24°C and near 70% relative humidity for up to 19 days, visually assess the extent of fungal invasion on the leaves as a percentage of diseased leaf area.

[0446] Example of application 13. Preventive fungicide for white mold disease on soybeans caused by Sclerotinia sclerotiorum (SCLESC P1 mycelium). Prevention and control

[0447] Soybean seedlings were grown in pots. These plants were sprayed to drip rate with the aforementioned spray solution, which contained the active ingredients or mixtures at concentrations mentioned in the table below. The next day, the treated plants were inoculated with a biological malt suspension containing *Sclerotinia sclerotiorum* mycelium. The test plants were then incubated for 6 days in a greenhouse at 23°C and a relative humidity between 80% and 85%. The degree of fungal infection on the leaves was visually assessed as a percentage of diseased leaf area.

[0448] The results of the above-mentioned application examples are given in Tables 1 and 2 below.

[0449] Table 1: Application Examples 1-7

[0450]

[0451]

[0452] Table 2: Application Examples 8-13

[0453]

[0454] Semi-field experiment

[0455] Example of application 14. Activity against Asian soybean rust (bean-potato rust fungus) under semi-field conditions.

[0456] Soybeans in Brazil are grown in areas covered with insect-proof netting under natural temperature and light conditions. Seeds are sown in trays, allowed to germinate and grow for 14-23 days, and then transplanted into containers. Subsequently, the plants are allowed to regrow for 27-35 days before spraying.

[0457] Soybean plants were sprayed twice at 14-day intervals. The experimental formulation (100 g / L, SC) was mixed with water, and the adjuvant Mees was added at a rate of 0.5 L / ha. TM(BASF, soybean oil methyl ester 824.3 g / L, EC) was used to prepare the spray solution. The plants were sprayed from a mobile spray booth with a horizontal boom. The spray solution was applied using a flat fan nozzle at a spray volume of 500 L / ha. Formulations and dosage rates for single treatments are given in the table below.

[0458] One day after each spraying application, plants were inoculated with a suspension of natural spores of *Dioscorea bean*. After each inoculation, the plants were cultured in a mobile chamber equipped with a misting system under saturated humidity.

[0459] Fourteen days after the second application, assess soybean rust infection as a percentage of infected leaf area (B14). Convert these percentage values ​​to efficacy. Calculate efficacy (E) using Abbot's formula as follows:

[0460] E = (1 - α / β) · 100

[0461] α corresponds to the fungicidal growth of the treated variant, expressed as a percentage, and

[0462] β corresponds to the fungicidal growth of the inactive control variant, expressed as a percentage.

[0463] Efficacy 0 means that the infection level of the treated variant corresponds to the infection level of the untreated control; efficacy 100 means that the treated variant did not show any symptoms.

[0464] The results of the above-mentioned application examples are given in Tables 3 to 7 below.

[0465] Table 3 Example of application 14

[0466]

[0467] Table 4 Example of application 14

[0468]

[0469] Table 5 Example of application 14

[0470]

[0471] Table 6 Example of application 14

[0472]

[0473] Table 7 Example of application 14

[0474]

[0475] field trials

[0476] Example of application 15. Field activity against wheat stalk rust fungus (PUCCRT, brown rust on wheat).

[0477] Trials were conducted in Spain under field conditions. Spring wheat was planted and grown with adequate water and nutrient supply. Two applications of the test compound (A and B) were performed at the onset of disease (application A) and at a second application 22 days later (application B). Spray solutions were prepared by mixing the experimental formulation of the test compound (50 g / L, EC) in water with 124 g / ha of Plurafac LF301 and Plurafac LF1312 (BASF, a low-foaming nonionic surfactant composed of alkoxylated, predominantly unbranched fatty alcohols containing higher olefin oxides and ethylene oxide), respectively. The spray solutions were applied using a flat fan nozzle at a spray volume of 300 l / ha.

[0478] The infection level of brown rust (wheat stalk rust) was evaluated 23 days after the second fungicide treatment (B23), and the average flag leaf level was calculated. Additionally, efficacy was calculated using the Albert formula, as in application example 14.

[0479] The results of the above-mentioned application example 15 are given in Tables 8 to 10.

[0480] Table 8 Example of application 15

[0481]

[0482] Table 9: Example of application 15

[0483]

[0484] Table 10: Example of application 15

[0485]

Claims

1. A compound of formula I, in, R 1 Selected from O and NH; R 2 Selected from CH and N; R a4 Selected from halogens, methyl groups, and methoxy groups; R a Selected from halogens, methyl groups, and methoxy groups; n is an integer selected from 1 and 2; And its stereoisomers and tautomers, as well as its N-oxides and agriculturally acceptable salts.

2. The compound according to claim 1, wherein, In equation I, R 1 Selected from O and NH; and R 2 Selected from CH and N, provided that R 1 In the case of NH, R 2 It is N.

3. The compound according to claim 1, wherein, In equation I, R 1 Selected from O; and R 2 It is CH.

4. The compound according to any one of claims 1 to 3, wherein, In equation I, n is 2.

5. The compound according to any one of claims 1 to 4, wherein, In equation I, R a4 Selected from halogens and methoxy groups.

6. The compound according to claim 5, wherein, In equation I, R a4 It is F.

7. The compound according to any one of claims 1 to 5, wherein, In equation I, R a Selected from halogens.

8. The compound according to claim 7, wherein, In equation I, R a It is F.

9. An agricultural chemical composition comprising an adjuvant and at least one compound of Formula I according to any one of claims 1 to 8, or a stereoisomer thereof, or an agriculturally acceptable salt, tautomer, or N-oxide thereof.

10. The agricultural chemical composition according to claim 9, comprising an additional pest control agent II different from the compound of formula I.

11. Use of the compound of formula I according to any one of claims 1 to 8 or the agricultural chemical composition according to claims 9 and 10 for combating plant pathogenic fungi.

12. A method for combating plant pathogenic fungi, the method comprising: To treat, and / or preventively treat, plants at risk of infection by the plant pathogenic fungus or plant propagation material thereof with at least one compound of Formula I according to any one of claims 1 to 8 or an agricultural chemical composition according to claims 9 and 10, and / or to apply to the plant pathogenic fungus at least one compound of Formula I according to any one of claims 1 to 8 or an agricultural chemical composition according to claims 9 and 10.

13. The method of claim 12, wherein the method is used to combat plant pathogenic fungi containing F129L amino acid substitutions in mitochondrial cytochrome b protein that confer resistance to Qo inhibitors, the method comprising: To treat, and / or preventively treat, plants at risk of infection by the plant pathogenic fungus or plant propagation material thereof with an effective amount of at least one compound of formula I according to any one of claims 1 to 8 or an agricultural chemical composition according to claims 9 and 10, and / or to apply to the plant pathogenic fungus an effective amount of at least one compound of formula I according to any one of claims 1 to 8 or an agricultural chemical composition according to claims 9 and 10.

14. The use according to claim 11 or the method according to claim 12 or 13, wherein, These plant pathogenic fungi contain F129L, an amino acid substitution in mitochondrial cytochrome b protein that confers resistance to Qo inhibitors.

15. The use according to claim 11 or 14, or the method according to any one of claims 12 to 14, wherein, These plant pathogenic fungi are rust fungi from the order Styloidea.

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