TW202229241A - Nematocidal compounds and use thereof - Google Patents

Abstract

The present invention relates to novel N-linker heterocyclic fluoroalkenyl compounds of formula (I),

wherein, R ¹, R ², R ³, ring A and Y are as defined in the detailed description. The present invention further relates to their preparation and their use to protect crops against undesired phytopathogenic microorganisms, e.g. against phytopathogenic fungi and pests such as nematodes.

Description

Nematicidal compounds and their uses

The present invention relates to novel nematicidal compounds. More particularly, the present invention relates to N-linked heterocyclic fluoroalkenyl compounds of formula (I) and processes for their preparation. The present invention further relates to the use of compounds of formula (I) as crop protection agents for controlling pests such as plant parasitic nematodes.

PCT Patent Publication No. WO2019186498, PCT Patent Publication No. WO2020075107, PCT Patent Publication No. WO2003042153, and PCT Patent Publication No. WO9708130 disclose that fluoroalkenyl heterocyclic compounds exhibit nematicidal activity, including heterocycles of heteroatoms such as nitrogen, sulfur and oxygen Attached to the fluoroalkene group through a C-linker. In addition, PCT Patent Publication No. WO2020157668 discloses that caffeine or theophylline derivatives have nematicidal activity.

Controlling damage to crops by phytopathogenic microorganisms and pests is important for achieving high crop efficiency. For example, damage to ornamental plants, vegetables, crops, cereals, and fruit crops caused by plant diseases can result in a significant drop in productivity, resulting in increased costs to consumers. Even though many products are available to control such damage, there is still a need for new compounds that are more effective, less expensive, less toxic, environmentally safer and/or have different modes of action.

The effectiveness of difluorobutene, trifluorobutene and other compounds described in the prior art is unsatisfactory in terms of efficacy, cost of treatment under real conditions, phytocompatibility, etc. Therefore, the development of finding novel pesticidal compounds to avoid and/or control the resistance of microorganisms (eg fungal or bacterial pathogens or pests) to known active ingredients under more favorable conditions has been of great interest in the agricultural field. Therefore, it is of particular interest to use new compounds that are more active than known compounds, with the aim of reducing the amount of active compound used while maintaining its effectiveness and long-lasting activity at least in a manner comparable to known compounds.

The present invention describes compounds of formula (I) which have the aforementioned effects or advantages. The compounds of the formula (I) according to the present invention, ie N-linked heterocyclic fluoroalkenyl compounds in which the ring of the heterocycle is substituted, exhibit unexpectedly and significantly against unwanted pests such as plant parasitic nematodes high activity.

式(I) 其中，R ¹、R ²、R ³、環A以及Y係於說明書定義。 The present invention relates to novel N-linked heterocyclic fluoroalkenyl compounds of formula (I).

Formula (I) wherein R ¹ , R ² , R ³ , ring A and Y are defined in the specification.

In one embodiment, the present invention provides a method of preparing a compound of formula (I).

In another embodiment, the present invention provides the use of a compound of formula (I) as a crop protection agent for controlling pests, especially plant parasitic nematodes.

definition:

The definitions in this specification are for illustrative purposes only, and do not limit the scope of the invention disclosed in this specification in any way.

As used herein, the terms "comprises, comprising, includes, including," "has, having," "contains, containing," "characterized by," or any other variation thereof, to cover non-exclusive inclusion, subject to any limitations expressly stated. For example, a composition, mixture, process or method consisting of a list of elements is not necessarily limited to only those elements, but may also include elements not expressly listed or other elements inherent to such composition, mixture, process or method.

The conjunction "consisting of" excludes any unspecified element, step or ingredient. If present in a claim, it will make the claim incapable of containing materials other than those stated, except as impurities normally associated with it. When the phrase "consisting of" appears in a sentence in the body of a claim, rather than immediately following the preamble, it restricts only the elements specified in the sentence; other Elements are not excluded from the overall request item.

The connective phrase "consisting essentially of" is used to define a composition or method comprising materials, steps, features, ingredients or elements that, unless disclosed by context, are The additional materials, steps, features, ingredients or elements do not materially affect the basic and novel characteristics of the claimed invention. The phrase "consisting essentially of" occupies the middle position between "comprising" and "consisting of."

Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or". For example, a condition A "or" B is satisfied by any of the following: A is true (or exists), B is false (or does not exist), A is false (or does not exist), and B is true (or exists) ), and both A and B are true (or exist).

Likewise, the indefinite article "a" (a and an) preceding an element or component of the invention is intended not to limit the instance (ie, the number of occurrences) of that element or component. Thus, "a" (a or an) should be read to include one or at least one, and the singular word form of an element or component also includes the plural unless the number clearly refers to the singular.

As described in this specification, the term "pesticide" in each case always includes the term "crop protection agent".

The term "invertebrate pest" includes pests of economic importance such as arthropods, gastropods and nematodes. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs, and other Stylommatophoras. The term "nematode" refers to living organisms of the phylum Phylum Nematoda. The term "helminths" includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), echinocephalus, and tapeworms (Cestoda).

The term "undesired microorganisms" or "phytopathogenic microorganisms", such as fungal or bacterial pathogens, includes the classes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, respectively. Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

In the context of this specification, "invertebrate pest control" refers to the inhibition of invertebrate pest development (including mortality, reduced feeding and/or disruption of mating), and related terms are similarly defined.

The term "agronomic" refers to the production of field crops, such as for food and fiber, and includes corn, soybeans and other legumes, rice, grains (eg, wheat, oats, barley, rye, rice, corn), Leafy vegetables (such as lettuce, cabbage and other rape crops), fruit vegetables (such as tomatoes, peppers, eggplants, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (such as pome, Stone fruits and citrus), small fruits (berries, cherries) and other specialty crops (eg canola, sunflowers, olives).

The term "nonagronomic" refers to crops other than crops, such as horticultural crops (eg, greenhouses, nurseries, or ornamentals not grown in the field), residential, agricultural, commercial, and industrial structures, turf (eg, turf farms) , pastures, golf courses, lawns, sports fields), wood products, stored products, agroforestry and vegetation management, public health (i.e. humans) and animal health (e.g. domesticated animals (e.g. pets, livestock and poultry) and undomesticated animals (e.g. such as wildlife)) applications.

Non-agronomic applications include the protection of animals from invertebrate parasitism by administering to the animal to be protected a parasiticidally effective (ie biologically effective) amount of a compound of the invention, usually in the form of a composition formulated for veterinary use Infestation of pests. As referred to in the description and claims of the present case, the terms "parasiticidal" (parasiticidal and parasiticidally) refer to providing an observable effect on invertebrate parasitic pests to protect animals from pests. Parasiticidal effects generally involve reducing the occurrence or activity of target invertebrate parasitic pests. Such effects on pests include necrosis, death, stunted growth, reduced mobility or ability to remain in or within the host animal, reduced feeding and suppressed reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection in animals.

The compounds of the present invention may exist in pure material form or as a mixture of different possible isomeric forms (eg, stereoisomers or structural isomers). Different stereoisomers include enantiomers, diastereoisomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, Polymorphs and geometric isomers. Any contemplated mixtures of these isomers also fall within the scope of the claims in this case. One of ordinary skill in the art will understand that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to or separated from other isomers. Furthermore, those of ordinary skill in the art are aware of processes or methods or techniques for separating, concentrating and/or selectively preparing such isomers.

Definitions of various terms in the specification will now be explained:

The term "alkyl", whether used alone or in a compound form (e.g. "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkane or alkylsulfonamido groups, including linear or branched C ₁ to C ₂₄ alkyl groups, preferably C ₁ to C ₁₅ alkyl groups, more preferably C ₁ to C ₁₀ alkyl groups, most preferably C ₁ to _C6 alkyl. Non-limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl , 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3 ,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl Alkyl-1-methylpropyl and 1-ethyl-2-methylpropyl or different isomers. If the alkyl group is at the end of the compound substituent, such as in an alkylcycloalkyl, the compound substituent The starting moiety of , such as cycloalkyl, may be mono- or polysubstituted, identically or differently and independently, by alkyl. The same applies to composite substituents, where other groups such as alkenyl, alkynyl, hydroxyl, Halogen, carbonyl, carbonyloxy, etc. are located at the terminals.

The term "alkenyl", whether used alone or in compound form, includes straight or branched C ₂ -C ₂₄ alkenes, preferably C ₂ -C ₁₅ alkenes, more preferably C ₂ -C alkenes. C ₁₀ olefins, most preferably C ₂ -C ₆ olefins. Non-limiting examples of olefins include vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Alkenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl Alkenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl yl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl yl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl yl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentene base, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl -3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl , 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl , 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl -1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2 ,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butene base, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and different isomers . The term "alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to an alkenyl group that is part of a composite substituent, eg, alkenyl and the like, unless specifically defined elsewhere.

The term "alkynyl", whether used alone or in compound form, includes straight or branched C ₂ -C ₂₄ alkynes, preferably C ₂ -C ₁₅ alkynes, more preferably C ₂ - _C10 alkynes, most preferably C2 _{- C6} alkynes. Non-limiting particles of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl base, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2- Methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl , 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl yl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl base, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl base, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2 -butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and different isomers. This definition also applies to an alkynyl group that is part of a composite substituent, eg, alkynyl, and the like, unless specifically defined elsewhere. The term "alkynyl" may also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.

The term "cyclic alkyl" (cyclic alkyl or cycloalkyl) refers to an alkyl group that is closed to form a ring. Non-limiting examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Unless specifically defined elsewhere, this definition also applies to a cycloalkyl group that is part of a composite substituent, eg, cycloalkylalkyl, and the like.

The term "cycloalkenyl" refers to an alkenyl group that is closed to form a ring that includes a monocyclic, partially unsaturated group. Non-limiting examples include, but are not limited to, cyclopentenyl and cyclohexenyl. This definition also applies to a cycloalkenyl group that is part of a composite substituent, eg, cycloalkenylalkyl, and the like, unless specifically defined elsewhere.

The term "cycloalkynyl" refers to an alkynyl group that is closed to form a ring that includes a monocyclic, partially unsaturated group. This definition also applies to a cycloalkynyl group that is part of a composite substituent, eg, cycloalkynylalkyl, and the like, unless specifically defined elsewhere.

The terms "cycloalkoxy", "cycloalkenyloxy" and the like are defined similarly to the above examples. Non-limiting examples include, but are not limited to, cyclopropanoxy, cyclopentanoxy, and cyclohexaneoxy. Unless specifically defined elsewhere, this definition also applies to cycloalkoxy as part of a composite substituent, eg, cycloalkoxyalkyl, and the like.

The term "alkoxy", whether used alone or in the form of a compound word, includes linear or branched C ₁ -C ₁₅ alkoxy, preferably C ₁ -C ₁₀ alkoxy, more Preferably it is C ₁ -C ₆ alkoxy. Examples of alkoxy groups include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- Dimethylethoxy, pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethyl Propoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methyl Pentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-di Methylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2- Trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy and different isomers thing. Unless specifically defined elsewhere, this definition also applies to alkoxy groups that are part of a composite substituent, eg, haloalkoxy, alkynylalkoxy, and the like.

The term "alkylthio" includes branched or straight chain alkylthio functional groups such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio base, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylethylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylthio Propylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methyl Pentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutyl Thio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methyl Different isomers such as propylthio.

The term "hydroxy" refers to -OH and "amino" refers to -NRR, where R can be H or any possible substituent such as alkyl. "Carbonyl" means -C(=O)-, "Carbonyloxy" means -OC(=O)-, "Sulfinyl" means SO, "Sulfonyl" means S(O) ₂ .

The term "halogen", whether used alone or in compound form (eg "haloalkyl"), includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as "haloalkyl," the alkyl group may be partially or fully substituted with halogen atoms, which may be the same or different.

Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromethyl Fluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl Fluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl , pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl and 1,1,1-trifluoropropan-2-yl. Unless specifically defined elsewhere, this definition also applies to haloalkyl groups that are part of a composite substituent, eg, haloalkylaminoalkyl, and the like.

The terms "haloalkenyl", "haloalkynyl" are defined similarly, except that alkenyl and alkynyl are present as part of a substituent rather than an alkyl group.

The term "haloalkoxy" refers to a straight or branched chain alkoxy group wherein some or all of the hydrogen atoms in these groups may be replaced by the halogen atoms described above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro Fluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2 -Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro -2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. Unless specifically defined elsewhere, this definition also applies to haloalkoxy as part of a composite substituent, eg, haloalkoxyalkyl, and the like.

The term "haloalkylthio" or "haloalkylsulfanyl" refers to a straight or branched chain alkylthio group in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as described above . Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloro Fluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2-difluoroethylthio Fluoroethylthio, 2-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio group, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1, 1,1-Trifluoropropan-2-sulfanyl. Unless specifically defined elsewhere, this definition also applies to haloalkylthio as part of a composite substituent, eg, haloalkylthioalkyl, and the like.

Non _- limiting examples of "haloalkylsulfinyl" include _CF3S (O), _CCl3S (O), _CF3CH2S (O), and _{CF3CF2S (} O). Non-limiting examples of "haloalkylsulfonyl" include _CF3S (O) ₂ , _CCl3S (O) ₂ , _CF3CH2S (O) ₂ , and _{CF3CF2S (} O ₎ ) ₂ .

Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butyl sulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl Propylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl base, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutyl Sulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethyl Propylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl Sulfonyl and different isomers.

Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-Methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2 -Methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1 -Dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl Sulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl base, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl , 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1methylpropyl Sulfonyl and 1-ethyl-2-methylpropylsulfonyl and different isomers.

The term "arylsulfonyl" includes Ar-S(O) ₂ , where Ar can be any carbocyclic or heterocyclic ring. Unless specifically defined elsewhere, this definition also applies to an alkylsulfonyl group as part of a composite substituent, eg, an alkylsulfonylalkyl group, and the like.

The term "ring" or "ring system" as a component of formula I is a carbocyclic or heterocyclic ring.

The term "ring system" refers to one or more rings.

The term "aromatic" means that Hueckel's law is satisfied, while the term "non-aromatic" means that Hueckel's law is not satisfied.

The term "carbocycle" or "carbocyclic" (carbocyclic or carbocyclyl) includes "aromatic carbocyclic ring system" or "nonaromatic carbocylic ring system" or polycyclic or Bicyclic (spiro, fused, bridged, nonfused) cyclic compounds, where the ring may be aromatic or non-aromatic (wherein aromatic means that satisfies Hückel law, non-aromatic means that Huckel's law is not satisfied).

Non-limiting examples of non-aromatic carbocyclic ring systems are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

Non-limiting examples of aromatic carbocyclic systems are phenyl, naphthyl, and the like.

The term "aryl" as used herein refers to any carbon-based aromatic group including, but not limited to, phenyl, naphthalene, biphenyl, anthracene, and the like. Aryl groups can be substituted or unsubstituted. In addition, aryl groups may be of a single ring structure or include multiple ring structures, which may be fused ring structures or one or more bridging groups attached through carbon-carbon bonds.

The term "hetero" in relation to rings refers to rings in which at least one ring atom is not carbon and may contain 1 to 4 heteroatoms independently selected from N, O, and S, provided that each ring contains no more than 4 nitrogens, not more than 2 oxygens and not more than 2 sulfurs.

The term "heterocycle" or "heterocyclic" includes "aromatic heterocycle" or "heteroaryl ring system" as well as "nonaromatic heterocycle ring system" or polycyclic or Bicyclic (spiro, fused, bridged, non-fused) ring compounds, wherein the ring may be aromatic or non-aromatic, wherein the heterocyclic ring contains at least one heteroatom selected from N, O and S(O) _0-2 , and/or the carbocyclic ring members of the heterocycle may be substituted by C(=O), C(=S), C(=CR*R*) and C=NR*, * denotes an integer.

The term "non-aromatic heterocycle" (non-aromatic heterocycle or non-aromatic heterocyclic) refers to three to fifteen members, preferably three to twelve, containing 1 to 4 heteroatoms selected from O, N and S Member saturated or partially unsaturated heterocycles: mono-, bi- or tricyclic heterocycles containing, in addition to carbocyclic members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygens and/or Sulfur atoms If the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to):

oxiranyl, oxetanyl, aziridinyl, azetidinyl, thietanyl, tetrahydrofuranyl ( tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl , thiazolidinyl, imidazolidinyl, oxadiazolidinyl, thiadiazolidinyl, triazolidinyl, dihydrofuryl, two Dihydrothienyl, pyrrolinyl, isoxazolinyl, isothiazolinyl, dihydropyrazolyl, dihydrooxazolyl, piper Piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxany, tetrahydropyranyl, tetrahydro tetrahydrothienyl; wherein the rings are connected to the skeleton through a carbon or nitrogen atom of the rings. This definition also applies to heterocycles that are part of a composite substituent, eg, heterocycloalkyl, and the like, unless specifically defined elsewhere.

The term "heteroaryl" or "aromatic heterocyclic" refers to a five- or six-membered, fully unsaturated monocyclic ring system containing 1 to 4 heteroatoms selected from O, N and S ; if the ring contains more than one oxygen atom, they are not directly adjacent; five-membered heteroaryl groups contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom; five-membered heteroaryl groups, In addition to carbon atoms, it can also contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom as ring members, for example (but not limited to): furyl (furyl), thienyl (thienyl) , pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadi oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl; wherein the rings are connected to the main chain through a carbon or nitrogen atom of the rings,

Six-membered heteroaryl groups containing 1 to 4 nitrogen atoms: in addition to carbon atoms, six-membered heteroaryl groups containing 1 to 3 and 1 to 4 nitrogen atoms as ring members, respectively, for example (but not limited to) : pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl.

Unless specifically defined elsewhere, this definition also applies to heteroaryl groups that are part of a composite substituent, eg, heteroarylalkyl, and the like.

The term "amide" refers to A-R'C=ONR''-B, where R' and R'' represent substituents and A and B represent any group.

The term "thioamide" refers to A-R'C=SNR''-B, where R' and R'' represent substituents and A and B represent any group.

The total number of carbon atoms in a substituent is indicated by the "C _i -C _j " prefix, where i and j are numbers from 1 to 21. For example, _{C1 -} C3alkoxy represents from methyl to propyl. In the above description, when compounds of formula (I) consist of one or more heterocycles, all substituents are attached to these rings through any available carbon or nitrogen by substituting a hydrogen on said carbon or nitrogen.

When a compound is substituted with a subscripted substituent indicating that the number of such substituents may exceed 1, then the substituents (when they exceed 1) are independently selected from the defined substituents Group. Furthermore, where a subscript indicates a range, eg (R) _ij , the number of substituents can be selected from an integer between i and j, inclusive.

When a group contains ^a substituent that may be ^hydrogen , such as R1 or R2, then the group is considered to be equivalent to unsubstituted when the substituent is considered to be hydrogen.

式(I) 其中， Y表示O或NR ⁵； R ¹係選自由H與F所組成的群組； R ²以及R ³係獨立地選自由H以及C ₁-C ₃烷基所組成的群組； 環A代表選自A1至A12的環系統，其中A係可選擇地由一或多個R ⁴取代；

R ⁴係選自由X、CN、(C=O)-R ⁶、R ^5aC=NOR ^5a、OR ⁵、N(R ⁵) ₂、S(O) _nR ⁶、C ₁-C ₆烷基、C ₁-C ₆鹵烷基、-C ₁-C ₆烷基-OR ⁵、C ₂-C ₆烯基、C ₂-C ₆炔基、C ₃-C ₁₂環烷基、C ₃-C ₁₀鹵環烷基、C ₃-C ₆環烷基-C ₁-C ₆烷基、苯基以及C ₃-C ₆雜環基所組成的群組；R ⁴的各基團可選擇地被選自鹵素、R ^5a、OR ^5a、SR ^5a、N(R ^5a) ₂、Si(R ^5a) ₃、COOR ^5a、CN以及CON(R ^5a) ₂所組成的群組的一或多個基團取代； R ⁵係選自由H、C ₁-C ₄烷基、C ₃-C ₆環烷基以及C ₃-C ₆環烷基-C ₁-C ₃烷基所組成的群組； R ^5a係選自由H、C ₁-C ₆烷基以及C ₃-C ₆環烷基所組成的群組； R ⁶係選自由N(R ^5a) ₂、C ₁-C ₆烷基、C ₂-C ₆烯基、C ₂-C ₆炔基、C ₁-C ₆鹵烷基、C ₂-C ₆鹵烯基、C ₂-C ₆鹵炔基以及C ₃-C ₆環烷基所組成的群組； R ¹、R ²、R ³、R ⁴、R ⁵、R ^5a以及R ⁶係可選擇地被選自X、CN、C ₁-C ₄烷基、O-C ₁-C ₄烷基、S(O) _n-C ₁-C ₄烷基以及C ₃-C ₆環烷基所組成的群組的一或多個取代； X表示鹵素； n表示整數，其中n=0、1以及2； 或者其農業上可接受的鹽、其立體異構物、其互變異構物或其N-氧化物。 Therefore, the present invention provides a compound of formula (I),

Formula (I) wherein, Y represents O or NR ⁵ ; R ¹ is selected from the group consisting of H and F; R ² and R ³ are independently selected from the group consisting of H and C ₁ -C ₃ alkyl Group; Ring A represents a ring system selected from A1 to A12, wherein ^A is optionally substituted with one or more R4;

R ⁴ is selected from X, CN, (C=O)-R ⁶ , R ^5a C=NOR ^5a , OR ⁵ , N(R ⁵ ) ₂ , S(O) _n R ⁶ , C ₁ -C ₆ alkyl , C ₁ -C ₆ haloalkyl, -C ₁ -C ₆ alkyl-OR ⁵ , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₁₂ cycloalkyl, C ₃ - The group consisting of C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl, phenyl and C ₃ -C ₆ heterocyclyl; each group of R ⁴ is optional One or more groups selected from the group consisting of halogen, R ^5a , OR ^5a , SR ^5a , N(R ^5a ) ₂ , Si(R ^5a ) ₃ , COOR ^5a , CN and CON(R ^5a ) ₂ group substitution; R ⁵ is selected from the group consisting of H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl and C ₃ -C ₆ cycloalkyl-C ₁ -C ₃ alkyl; R ^5a is selected from the group consisting of H, C ₁ -C ₆ alkyl and C ₃ -C ₆ cycloalkyl; R ⁶ is selected from N(R ^5a ) ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl and C ₃ -C ₆ cycloalkyl the group consisting of; R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ^5a and R ⁶ are optionally selected from X, CN, C ₁ -C ₄ alkyl, OC ₁ -C ₄ alkane One or more substitutions of the group consisting of radical, S(O) _n -C ₁ -C ₄ alkyl and C ₃ -C ₆ cycloalkyl; X represents halogen; n represents an integer, wherein n=0, 1 and 2; or an agriculturally acceptable salt thereof, a stereoisomer thereof, a tautomer thereof, or an N-oxide thereof.

R ⁴係選自由X、CN、R ^5aC=NOR ^5a、C ₁-C ₆烷基、C ₁-C ₆鹵烷基、C ₂-C ₆烯基、C ₂-C ₆炔基、C ₃-C ₁₂環烷基、C ₃-C ₁₀鹵環烷基、C ₃-C ₆環烷基-C ₁-C ₆烷基、苯基以及C ₃-C ₆雜環基所組成的群組；R ⁴的各基團可選擇地被選自鹵素、R ^5a、OR ^5a、SR ^5a、N(R ^5a) ₂、Si(R ^5a) ₃、COOR ^5a、CN以及CON(R ^5a) ₂所組成的群組的一或多個基團取代； R ⁴較佳地，係選自X、CN、C ₁-C ₆-烷基及C ₁-C ₆-鹵烷基； 以及/或者其立體異構物或其農業上可接受的鹽類或其互變異構物或其N-氧化物。 In one embodiment, the present invention provides a compound of formula (I), wherein Y represents O; Ring A represents a ring system selected from A1 to A7, wherein ^A is optionally substituted with one or more R4;

R ⁴ is selected from X, CN, R ^5a C=NOR ^5a , C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C The group consisting of ₃ -C ₁₂ cycloalkyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl, phenyl and C ₃ -C ₆ heterocyclyl Group; each group of R ⁴ is optionally selected from halogen, R ^5a , OR ^5a , SR ^5a , N(R ^5a ) ₂ , Si(R ^5a ) ₃ , COOR ^5a , CN and CON(R ^5a ) ₂ One or more groups of the formed group are substituted; R ⁴ is preferably selected from X, CN, C ₁ -C ₆ -alkyl and C ₁ -C ₆ -haloalkyl; and/or its Stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof.

R ⁴係選自由X、CN、R ^5aC=NOR ^5a、-C ₁-C ₆烷基-OR ⁵、C ₁-C ₆烷基、C ₁-C ₆鹵烷基、C ₂-C ₆烯基、C ₂-C ₆炔基、C ₃-C ₁₂環烷基、C ₃-C ₁₀鹵環烷基、C ₃-C ₆環烷基-C ₁-C ₆烷基、苯基以及C ₃-C ₆雜環基所組成的群組；R ⁴的各基團可選擇地被選自鹵素、R ^5a、OR ^5a、SR ^5a、N(R ^5a) ₂、Si(R ^5a) ₃、COOR ^5a、CN以及CON(R ^5a) ₂所組成的群組的一或多個基團取代； 以及/或者其立體異構物或其農業上可接受的鹽類或其互變異構物或其N-氧化物。 In one embodiment, the present invention provides a compound of formula (I), wherein Ring A represents a ring system selected from A8 to A12, wherein ^A is optionally substituted with one or more R4;

R ⁴ is selected from X, CN, R ^5a C=NOR ^5a , -C ₁ -C ₆ alkyl-OR ⁵ , C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ Alkenyl, C2 _{- C6alkynyl} , C3 _{- C12cycloalkyl} , C3 _{- C10halocycloalkyl} , C3- _C6cycloalkyl - _{C1 - C6alkyl} , phenyl and The group consisting of C ₃ -C ₆ heterocyclyl groups; each group of R ⁴ is optionally selected from halogen, R ^5a , OR ^5a , SR ^5a , N(R ^5a ) ₂ , Si(R ^5a ) ₃ , COOR ^5a , CN and one or more groups of the group consisting of CON(R ^5a ) ₂ are substituted; and/or its stereoisomer or its agriculturally acceptable salt or its tautomer or its N-oxide.

In one embodiment, the present invention provides a compound of formula (I), wherein preferably, ring A is selected from A1, A2, A6 and A7, wherein ^A is optionally substituted by one or more R4;

In one embodiment, the present invention provides a compound of formula (I), wherein Y represents O; Ring A represents a ring system selected from A1 to A12, wherein A is optionally substituted with one or more R ⁴ ; and R ⁴ is selected from the group consisting of X, CN, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, R ^5a C=NOR ^5a and -C ₁ -C ₆ -alkyl-OR ⁵ .

In one embodiment, the present invention provides a compound of formula (I), wherein the preferred compound is selected from the group consisting of: 4,4-difluorobut-3-en-1-yl 2-(5 -Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(tri Fluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1- yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl) acetate; 4,4-difluorobut-3- En-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl2 -(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(5-cyclopropane) yl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazole- 1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl ) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobutane- 3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 4-Methyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H - Pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-indazol-1-yl)acetate; 3,4,4-trifluorobutane -3-En-1-yl 2-(1H-indazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyridine azol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propionate; 3,4,4 -Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionate; 4,4-difluorobut-3-ene-1 -yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro -3,5-Dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl -1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl) Propionate; 4,4-Difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propionate; 3,4,4- Trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-( 4-Methyl-1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H- Pyrazol-1-yl)propionate; 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionic acid ester; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobutane- 3-En-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 3-(Difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-2H-indazole -2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate; 4,4-difluorobutane -3-En-1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2 -(3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazole -1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobutan-3- En-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-( Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl) )-1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyridine Azol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H - Pyrazol-1-yl)propionate; 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H - Pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(2H-indazol-2-yl)acetate; 4,4-difluoro But-3-en-1-yl 2-(2H-indazol-2-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl yl-1H-1,2,4-triazol-1-yl)acetate; 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobutane- 3-En-1-yl)acetamide; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl) Acetate; 3,4,4-Trifluoro But-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(3, 5-Dimethyl-1H-1,2,4-triazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl- 1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2 - Methylpropionate; 2-(4-Chloro-1H-pyrazol-1-yl)-N-(4,4-difluorobut-3-en-1-yl)acetamide; 3,4 ,4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 4, 4-Difluorobut-3-en-1-yl 2-(1H-imidazol-1-yl) acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-( Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl- 1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl- 1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1- yl)-2-methylpropionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl) Propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propionate; 4,4-Di Fluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl) 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)acetate ; 4,4-Difluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-Difluorobut-3- En-1-yl 2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 1H-benzo[d][1,2,3]triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d][ 1,2,3]Triazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-1H-tetrazol-1-yl) Acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 4, 4-Difluoro But-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-ene -1-yl 2-(3-chloro-1H-indazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl -1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1- base) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl) acetate; 3, 4,4-Trifluorobut-3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropionate; 3,4,4-Trifluorobutane- 3-En-1-yl 2-(1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(1H- Pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propane 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-phenyl-1H-pyrazol-1-yl)acetate; 3,4,4-Trifluorobut-3-ene -1-yl 2-(4-chloro-3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-ene -1-yl 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-ene -1-yl 2-(4-(3,5-difluorophenyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2 -(2H-benzo[d][1,2,3]triazol-2-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl) yl-2H-tetrazol-2-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]tris azol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1- yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4, 4-Trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropanoate; 3,4, 4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropionate; 3,4, 4-Trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propionate; 3,4,4-Trifluorobutan-3 -En-1-yl 2-(4-chloro-1H - Pyrazol-1-yl)butyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-methyl-1H-pyrazol-1- base) butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3, 4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4 -Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobutane- 3-en-1-yl 2-(3-methyl-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(3- Methyl-1H-indazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)- 3-Methylbutyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)- 3-Methylbutyrate; 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyridine oxazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazole- 1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)- 3-Methylbutyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-3-methyl Butyrate; 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-1H-pyrazol-1-yl)butyrate; 3,4 ,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate and 3,4,4- Trifluorobut-3-en-1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1-yl)butyrate.

If the individual components have different biological activities, in each case isolate or synthesize biologically more efficient isomers (e.g. specific enantiomers or non-spiroisomers, or mixtures of isomers (e.g. Enantiomer mixtures or diastereomer mixtures)) may be advantageous.

The compounds of formula (I) and their tautomers, in each case in free form or in salt form, are also available in hydrated form, if appropriate and/or include other solvents such as those which may have been used for crystallization in solid form compounds present.

Compounds of the invention as defined in Formula (I) and/or Table (1) can be prepared by the following schemes, wherein, unless otherwise stated, each variable for the compounds of Formula (I) is as defined above.

Scheme: 1 (Ring A: Ring A; Base: Base; Solvent: Solvent)

As shown in Scheme 1, compounds of formula 4 are permeable through compounds of formula 2 in the presence of an organic or inorganic base such as potassium carbonate or cesium carbonate and a suitable solvent such as acetonitrile or N,N-dimethylformamide Alkylation preparation with alkyl haloacetate compounds of formula 3, usually with heating. Afterwards, the compound of formula 4 is hydrolyzed in the presence of a suitable acid or base to obtain the compound of formula 5. Suitable acids that can be used for hydrolysis are selected from hydrochloric acid or trifluoroacetic acid in the presence of a suitable solvent such as tetrahydrofuran, 1,4-dioxane, methanol or water, and can be used with Suitable bases for hydrolysis are selected from sodium hydroxide or lithium hydroxide.

Scheme: 2 (Ring A: Ring A; Base: Base)

In addition, as shown in Scheme 2, in an organic or inorganic base such as N,N-diisopropylethylamine, potassium carbonate or cesium carbonate, and a suitable solvent such as acetonitrile and N,N-dimethylformamide ), compounds of formula 1a can be prepared by alkylation of compounds of formula 5 with fluorobutenyl halides of formula 6, usually with heating.

Scheme: 3 (Ring A: ring A; Amide Coupling: amide coupling; Base: base)

As shown in Scheme 3, the compound of formula 1b can be synthesized by different coupling agents such as N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (N-(3 -Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCI)), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU) or a halogenating agent such as SOCl ₂ , SO ₂ Cl ₂ , COCl ₂ , X ₂ and methanesulfonyl chloride), preferably in the presence of a suitable base such as triethylamine or diisopropylethylamine. In addition, in the presence of a base such as carbonic acid Compounds of formula 1c can be prepared by alkylation of compounds of formula 1b with haloalkanes in the presence of a suitable solvent such as acetonitrile or N,N-dimethylformamide, usually at Room temperature and heating conditions.

Depending on the number of asymmetric centers in the compound, any compound according to the present invention may exist as one or more optical, geometric or chiral isomers. Accordingly, the present invention also relates to all optical isomers and their racemic or irregular mixtures (the term "scalemic" means mixtures of enantiomers in different proportions), and all possible stereoisomers of all proportions of the mixture. Astereoisomers and/or optical isomers can be prepared according to methods known to those of ordinary skill in the art.

Depending on the number of double bonds in the compound, any compound according to the present invention may exist as one or more geometric isomers. Accordingly, the present invention also relates to all geometric isomers and all possible mixtures in all ratios. Geometric isomers can be prepared according to methods known to those of ordinary skill in the art.

amorphic Depending on the compound's preparation, purification storage, and other various influencing factors, any compound according to the invention may exist in one or more amorphic or isomorphic or polymorphic forms. Accordingly, the present invention also relates to amorphous, isomorphic and polycrystalline forms in all possible proportions. Amorphous, isomorphic and polymorphic forms can be prepared and/or isolated and/or purified according to methods known to those of ordinary skill in the art.

There are a number of suitable standard methods such as alkylation, halogenation, amidation, amination, oximation, oxidation and reduction. The choice of a suitable preparation method depends on the nature (reactivity) of the substituents of the intermediate product. These reactions can be conveniently carried out in a solvent. They can also be carried out at different temperatures, usually in an inert environment. The reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal amides. Acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines , free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, diisopropylamine Lithium, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, N,N-diisopropylethylamine, triethylenediamine, cyclohexylamine, N-ring Hexyl-N,N-dimethylamine, N,N-diethylaniline, pyrimidine, 4-(N,N-dimethylamino)pyrimidine, quinuclidine, N-methylmorpholine , benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (1,8-diazabicyclo[5.4.0]undec-7 -ene (DBU)).

The reaction according to Scheme-1 or Scheme-3 is preferably carried out in a solvent selected from standard solvents which are inert under the main reaction conditions. Preferably aliphatic, cycloaliphatic or aromatic hydrocarbons (such as petroleum ether, hexane, toluene); halogenated hydrocarbons (such as chlorobenzene, dichloromethane, chloroform, carbon tetrachloride or dichloroethane) ; ethers (such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), dioxane, tetrahydrofuran or 1,2-dimethoxyethane); nitriles (such as acetonitrile or propionitrile) or amides (such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methylcarbanilide, N-methylpyrrolidone (NMP) ) or hexamethylenephosphoric triamide); esters (such as methyl acetate or ethyl acetate); sulfites (such as dimethylsulfoxide (DMSO)); sulfites (such as cyclobutane) ); alcohols (e.g. methanol, ethanol, isopropanol, 1,1-, iso-, sec- or tert-butanol, ethylene glycol, propane-1,2-diol, ethoxyethanol, methoxy ethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether) or mixtures of these compounds.

The reactants can react with each other in such a way that no solvent or diluent is added. The reaction is advantageously carried out at a temperature ranging from about -80°C to about +140°C, preferably about -30°C to about +100°C, and in many cases at ambient temperature and about +80°C within the range between.

A compound of formula (I) can be converted into another compound of formula (I) in a manner known per se by substituting one or more substituents of the starting compound of formula (I) in a conventional manner for another compound according to the invention (Other) Substituents. Depending on the selected reaction conditions and the suitable starting materials in each case, for example, only one substituent can be replaced in one reaction step with another substituent according to the invention, or multiple substitutions can be made in the same step. groups are substituted with other substituents according to the present invention. Salts of compounds of formula (I) can be prepared according to methods known per se. Thus, for example, acid addition salts of formula (I) can be obtained by treatment with suitable acids or suitable ion exchange reagents, and salts thereof with bases can be obtained by treatment with suitable bases or suitable ions obtained by exchanging reagents. The choice of salt depends on its tolerance to the use of the compound, eg agricultural tolerance or physiological tolerance. Salts of compounds of formula (I) can be converted in a conventional manner to free compounds of formula I, acid addition salts (for example, by treatment with a suitable acid or a suitable ion exchange reagent) and salts with bases ( For example, treatment with a suitable base or a suitable ion exchange reagent). Salts of compounds of formula (I) can be converted in a manner known per se to other salts of compounds of formula (I), such as acid addition salts, for example by treatment of mineral acids in suitable solvents. Salts (such as hydrochloride) with suitable metal salts (such as sodium, barium or silver salts of acids, for example with silver acetate), wherein the inorganic salts formed (such as silver chloride) are insoluble, and therefore from Precipitated in the reaction mixture.

In one embodiment, the present invention provides compounds of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides or compositions or compositions thereof for use in the control or prevention of crops and/or use of horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes or mites.

In preferred embodiments, the present invention provides compounds of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides or compositions or compositions thereof for use in controlling or Use of crops and/or horticultural crops for prevention against nematodes and phytopathogenic fungi.

Crop line is selected from cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa , sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers, other vegetables or ornamental plants.

The compounds according to the invention can be used for the control or eradication of pests, such as nematodes, which are especially present in plants, especially in practical and ornamental plants in agriculture, horticulture and forests, or in organs such as tubers, seeds or roots In some cases, even plant organs formed at a later point in time are protected from these pests.

The compounds of formula (I) according to the invention are active ingredients of prophylactic and/or therapeutic value in the field of pest control, even at low application rates, for use against pesticide-resistant pests, such as nematodes. Furthermore, the compounds of formula (I) have a very favourable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Accordingly, the present invention also provides a pesticidal composition comprising a compound of the present invention (eg formula (I)). It has now been found that the compounds of the formula (I) according to the invention have a very favourable spectrum of activity and protect animals and practical plants from attack and damage by nematodes. Accordingly, the present invention also provides a nematicidal composition comprising a compound of the present invention (eg formula (I)).

The compounds of formula (I) have potent nematicidal activity and can be used for controlling unwanted nematodes and bacteria in agricultural or horticultural crop protection and in protecting the face of such materials.

The compounds of formula (I) are useful as nematicides in crop protection, for example for the control of Tylenchida, Rhabditida, Dorylaimida and Tryplonchida.

The compounds of formula (I) can be used to control or prevent phytopathogenic nematodes of crops and/or horticultural crops.

The compounds of formula (I) can be used to protect crops, wherein the crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, Oil plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers, other vegetables and ornamental plants.

The compounds of formula (I) are particularly suitable for controlling nematodes. Therefore, in another aspect, the present invention also relates to a method for controlling damage to plants or parts thereof by plant-parasitic nematodes (endo-, semi-endo- and ectoparasitic nematodes), in particular the following plant-parasitic nematodes Nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria, and other root knot nematodes Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Eelonolaimus longicaudatus, and other spiny nematodes Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; Ring nematodes, Criconema species, small Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus d estructor), Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus) and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species, and Hemicriconemoides species; Hirshmanniella species); Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, long needle Nematodes (Longidorus elongatus) and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, banana piercing Nematodes (Radopholus similis) and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus s pecies); Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other stunt nematodes; Citrus nematodes, Stunt nematodes Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant-parasitic nematode species such as Subanguina spp., Hypsoperine spp. ), Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

In particular, nematode species, Meloidogyne spp., Heterodera spp., Rotylenchus spp., Pratylenchus spp., and Introgressive nematodes (Radopholus spp.) can be controlled by the compounds of the present invention.

In one embodiment, the present invention provides a composition for controlling or preventing phytopathogenic microorganisms, comprising a compound of general formula (I), a stereoisomer, an agriculturally acceptable salt, a tautomer or an N- oxide and one or more inert supports.

In another embodiment, the composition may further comprise one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides , plant growth regulators, antibiotics, nutrients or fertilizers.

The concentration range of the compound of general formula (I) is 1 to 90% by weight relative to the total weight of the composition, preferably 5 to 50% by weight relative to the total weight of the composition.

The present invention further relates to a composition for controlling unwanted microorganisms comprising at least one compound of formula (I) and one or more inert carriers. Inert carriers further include agriculturally suitable adjuvants, solvents, diluents, surfactants and/or extenders and the like.

The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one compound of formula (I) and/or one or more active compatible compounds selected from fungicides, insecticides , acaricides, nematicides, herbicides, bioinsecticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.

Generally, the compounds of the present invention are used in the form of compositions (eg, formulations) that include a carrier. The compounds of the present invention and their compositions can be used in various forms such as aerosol dispensers, capsule suspensions, cold fogging concentrates, dustable powders, emulsifiable concentrates concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder , oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, pesticide coated Seed (seed coated with a pesticide), soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate) , ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water dispersible granules or tablets tablets), water dispersible powder for slurry treatment, water-soluble granules or tablets (water sol) uble granules or tablets), water soluble powder for seed treatment and wettable powder.

Formulations generally include a liquid or solid carrier and optionally a conventional formulation adjuvant, which may be a solid or liquid adjuvant, for example, an unepoxidized or epoxidized vegetable oil (e.g., epoxidized coconut oil, rapeseed oil) or soybean oil), defoamers (such as silicone oil), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, binders and/or tackifiers. The composition may further include fertilizers, micronutrient donors, and other agents that affect plant growth, as well as include compounds containing the present invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides agents, plant activators, acaricides and insecticides.

Accordingly, the present invention also provides a composition comprising a compound of the present invention and an agricultural carrier and optionally a first or more conventional formulation adjuvants.

In the absence of adjuvants, for example by grinding, screening and/or compressing the solid compounds of the present invention, and in the presence of at least one adjuvant, for example by conflating the compounds of the present invention with adjuvant(s) Mixed and/or milled, the compositions are prepared by known methods. In the case of the invention as a solid compound, the grinding/milling of the compound is to ensure a specific particle size. The preparation of these compositions and the use of the compounds of the present invention to prepare these compositions are also the subject of the present invention.

Examples of compositions used in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, sprayable or dilutable solutions, spreadable pastes pastes), dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations of various substances in polymeric substances), which include at least the compounds according to the invention, and the type of composition should be chosen according to the intended purpose and the circumstances at the time.

Examples of suitable liquid carriers are unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the _C8 to C12 moieties _of alkylbenzenes, such as xylene mixtures, alkylnaphthalenes or tetralins, aliphatic or cycloaliphatic hydrocarbons (such as paraffin or cyclohexane), alcohols (such as ethanol, propanol or butanol), ethylene glycol and its ethers and esters (such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol) glycol monoethyl ether), ketones (such as cyclohexanone, isophorone or diacetone alcohol), strongly polar solvents (such as N-methylpyrrolidin-2-one, dimethylsulfoxide or N, N-dimethylformamide, water), unepoxidized or epoxidized vegetable oils (such as unepoxidized or epoxidized canola, castor, coconut, or soybean oil), and silicone oils. For example, examples of solid carriers for dusts and dispersible powders are generally ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. In order to improve the physical properties, high dispersity silica or high dispersity absorbent polymer can also be added. Suitable particulate adsorbent carriers for granules are porous types such as pumice, brick grit, sepiolite or bentonite, and suitable non-absorbent carriers are calcite or sand. Furthermore, it is also possible to use a large number of particulate materials of inorganic or organic nature, in particular dolomite or pulverized plant residues. Depending on the type of active ingredient to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties. The surfactants mentioned below are only examples, and a large number of other surfactants generally used in formulation technology and suitable for the present invention are also described in the relevant literature. Suitable nonionic surfactants are, in particular, polyglycol ether derivatives of saturated or unsaturated fatty acids or aliphatic or (cyclo)aliphatic alcohols of alkylphenols, which may contain from about 3 to about 30 Glycol ether groups and about 8 to about 20 carbon atoms in (cyclo)aliphatic hydrocarbon groups or about 6 to about 18 carbon atoms in alkylphenol groups. Also suitable are water-soluble polyoxyethylene adducts with polypropylene glycol, ethylenediamine polypropylene glycol or alkyl polypropylene glycol having 1 to about 10 carbon atoms in the alkyl chain, about 20 to about 250 carbon atoms in the alkyl chain glycol ether groups and from about 10 to about 100 propylene glycol ether groups. Generally, the above compounds will contain from 1 to about 5 ethylene glycol units per propylene glycol unit. Examples that may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol/polyoxyethylene adduct, tributylphenoxypolyethoxyethanol, polyethylene glycol alcohol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate. Cationic surfactants, especially quaternary ammonium salts, which generally have at least one alkyl group of about 8 to about 22 carbon atoms as a substituent and a lower alkyl or hydroxyalkyl group as a further substituent (unhalogenated or halogenated) or benzyl. It is preferably present in the form of a halide, methylsulfate or ethylsulfate. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.

Examples of suitable anionic surfactants are water-soluble soaps or water-soluble nucleating surface-active compounds. Examples of suitable soaps are alkali metal, alkaline earth metal or (substituted or unsubstituted) ammonium salts of fatty acids having about 10 to 22 carbon atoms, for example the sodium or potassium salts of oleic or stearic acid, Or the sodium or potassium salts of natural fatty acid mixtures obtainable, for example, from coconut oil or tall oil; mention must also be made of the fatty acid methyl taurates. However, synthetic surfactants are more commonly used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates ( alkylaryl sulfonates). Typically, fatty sulfonates and fatty sulfates exist as alkali metal, alkaline earth metal, or (substituted or unsubstituted) ammonium salts, which typically have alkyl groups of about 8 to about 22 carbon atoms, also alkyl groups is to be understood to include the alkyl moiety of the acyl group; examples that may be mentioned are the sodium or calcium salts of lignosulfonic acid of the dodecylsulphuric ester or fatty alcohols prepared from natural fatty acids Sodium or calcium salt of lignosulfonic acid of sulfate mixture. This group also includes the sulfate and sulfonate salts of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonyl groups and functional groups of fatty acids of about 8 to about 22 carbon atoms. Examples of alkylaryl sulfonates are the sodium salts, calcium salts of decylbenzenesulfonic acid, naphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensate salt or triethanolammonium salt. In addition, suitable phosphates are also possible, such as salts of phosphate esters of p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids .

Typically, the composition comprises 0.1 to 99% (especially 0.1 to 95%) of a compound of the invention and 1 to 99.9% (especially 5 to 99.9%) of at least one solid or liquid carrier, and generally, the composition of 0 to 25%, especially 0.1 to 20%, are surfactants (% in each case refers to weight percent). While concentrated compositions tend to be used in commercial products, end consumers typically use diluted compositions with significantly lower concentrations of active ingredients.

Examples of foliar formulation types of premix compositions are: GR: Granules EW: water emulsion (emulsions, oil in water) WP: Wettable Powder ME: micro-emulsion WG: water dispersable granules (powders) SC: aqueous suspension concentrate SG: water soluble granules CS: aqueous capsule suspension SL: Soluble OD: oil-based suspension concentrate, and EC: emulsifiable concentrate SE: Aqueous suspo-emulsion

Examples of types of seed treatment formulations for premix compositions are: WS: wettable powders for seed treatment slurry FS: suspending agent for seed treatment (solution for seed treatment) LS: solution for seed treatment WG: water dispersible granules, and ES: Emulsions for seed treatment CS: aqueous capsule suspension.

Examples of formulation types suitable for use in tank-mix compositions are solutions, diluted emulsions, suspensions or mixtures thereof, and powders.

As with the nature of the formulation, the method of application, such as foliar application, flooding, spraying, atomizing, dusting, spreading, spreading or pouring, is selected according to the intended target and the prevailing environment.

Tank mix compositions are typically prepared by diluting one or more premix compositions containing various pesticides and optionally other adjuvants with a solvent such as water. Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technology, such as natural or regenerated minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizer.

In general, tank mixes for foliar or soil application contain 0.1 to 20% (especially 0.1 to 15%) of the desired ingredients and 99.9 to 80% (especially 99.9 to 85%) of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 20% (especially 0.1 to 15%) of the tank mix formulation. Typically, premix formulations for foliar application comprise 0.1 to 99.9% (especially 1 to 95%) of the desired ingredients and 99.9 to 0.1% (especially 99 to 5%) of solid or liquid adjuvants (including, For example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 50% (especially 0.5 to 40%) of the premix formulation.

Typically, tank mix formulations for seed treatment applications contain 0.25 to 80% (especially 1 to 75%) of the desired ingredients and 99.75 to 20% (especially 99 to 25%) of solid or liquid adjuvants (including , for example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 40% (especially 0.5 to 30%) of the tank-mixed formulation.

Typically, premix formulations for seed treatment applications contain 0.5 to 99.9% (especially 1 to 95%) of the desired ingredients and 99.5 to 0.1% (especially 99 to 5%) of solid or liquid adjuvants (including , for example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of 0 to 50% (especially 0.5 to 40%) of the premix formulation, while the commercial product will preferably be formulated as a concentrate (eg, pre-mixed compositions (formulations)), whereas end users typically use diluted formulations (eg, tank-mixed compositions).

Preferred seed treatment premix formulations are aqueous suspensions. The formulations can be applied to the seeds using common processing techniques and machines, such as fluidized bed techniques, roller mill methods, roto static seed treaters, and roller coaters ( drum coaters). Other methods, such as spouted beds, may also be useful. Seeds can be sized prior to coating. After coating, the seeds are typically dried and transported to a sizing machine for sizing. These procedures are known. The compounds of the present invention are particularly suitable for soil and seed treatment applications.

In general, the premix compositions of the present invention contain from 0.5 to 99.9%, especially from 1 to 95%, advantageously from 1 to 50% of the desired ingredients (by mass) and from 99.5 to 0.1%, especially from 99 to 5% % solid or liquid adjuvant (by mass) (including, for example, a solvent such as water), wherein the adjuvant (or adjuvant) may be a surfactant in an amount of 0 to 50% of the premix formulation (especially 0.5 to 40%), by mass.

In a preferred embodiment independent of any other embodiments, the compound of formula (I) is in the form of a plant propagation material treatment (or protection) composition, wherein the plant propagation material protection composition may additionally comprise colorants. The plant propagation material protection composition may also include at least one polymer from the group consisting of water-soluble film-forming polymers and water-dispersible film-forming polymers, which improves the adhesion of the active ingredient to the treated plant propagation material, the polymer generally having an average The molecular weight is at least 10,000 to about 100,000.

In one embodiment, the present invention provides a method for controlling or preventing the infestation of practical plants by phytopathogenic microorganisms in crops and/or horticultural crops, wherein the compound of general formula (I) and/or a stereoisomer thereof or an agriculturally acceptable The salts or tautomers or N-oxides or compositions or compositions are applied to plants, parts thereof, or their locus.

In another embodiment, the present invention provides a method of controlling or preventing phytopathogenic nematodes in crops and/or horticultural crops from infesting utility plants, wherein the compound of general formula (I) and/or its stereoisomers or agriculturally acceptable The accepted salt or tautomer or N-oxide or composition or composition is applied to plant seeds.

In yet another embodiment, the present invention provides a compound of formula (1) and/or its stereoisomers or agriculturally acceptable salts or tautomers or N-oxides or compositions or compositions A method for controlling or preventing phytopathogenic nematodes in crops and/or horticultural crops, comprising the steps of: applying an effective dose of a compound or composition or composition ranging from 1 g to 5 kg per hectare of agricultural and/or horticultural crops.

Examples of methods of application of the compounds of the invention and their compositions, ie methods of controlling pests in agriculture, are spraying, atomizing, dusting, brushing, dressing, broadcasting or pouring, which will be selected to suit the circumstances of the intended purpose .

One method of application in agriculture is to the foliage of plants (foliar application), and the frequency and rate of application can be chosen to match the risk of infestation by the relevant pest or fungus. Alternatively, the active ingredient can reach the plant through the root system (systemic action) by applying the compound to the plant locus, for example, by applying a liquid composition of the compound to the soil (by saturating), or by applying the compound in solid form in granular form The compound is applied to the soil (soil application). In the case of rice plants, the granules can be metered into submerged paddy fields. Application of the compounds of the present invention to soil is the preferred method of application.

Typical application rates per hectare are generally 1 to 2000 g active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha, for example 50 to 300 g/ha.

In one embodiment, the present invention provides a seed comprising a compound of formula (I) and/or its stereoisomers, agriculturally acceptable salts, tautomers, N-oxides or compositions or compositions , wherein the compound of formula (I) or its N-oxide or agriculturally acceptable salt is present in an amount of 0.1 g to 10 kg per 100 kg of seeds.

The compounds according to the invention and their compositions are also suitable for the protection of plant propagation material, such as seeds, fruit, tubers or kernels, or nursery plants, against pests of the aforementioned types. Plant propagation material is treated with the above-mentioned compounds before planting, eg seeds can be treated before sowing. Alternatively, the compound can be applied to the kernels (coating) by soaking the kernels in a liquid composition or applying a layer of a solid composition. The composition can also be applied when the propagation material is planted to the application site, for example to the seed furrow during drilling. Methods for the treatment of these plant propagation materials and the plant propagation materials thus treated are further inventive subjects of the present invention. Typical treatment rates will depend on the plants and nematodes to be controlled, usually 1 to 200 g/100 kg of seed, preferably 5 to 150 g/100 kg of seed, for example 10 to 100 g/100 kg of seed . Application of the compounds of the present invention to seeds is the preferred method of application.

The term seed includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed fragments, suckers, corms, bulbs, fruits, tubers , grains, rhizomes, cuttings, cut strips, etc., in a preferred embodiment, refers to the seed.

The present invention also includes a seed which is coated or treated with a compound of formula I or contains a compound of formula I. The term "coated or treated and/or contained with a compound of formula I" generally means that most of the active ingredient is on the surface of the seed at the time of application, although more or less of the ingredient may penetrate into the seed material depending on the method of application. . When this seed product is (re)planted, it may absorb active substances. In one embodiment, the present invention provides a plant propagation material to which a compound of formula (I) is attached. Furthermore, there is provided a composition comprising plant propagation material treated with a compound of formula (I).

Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting pelleting). Seed treatment application of a compound of formula I is a preferred method of application, which can be carried out by any known method, such as spraying or dusting the seeds before sowing or during sowing/planting.

Suitable target plants are, in particular, cereals (such as wheat, rye, barley, oats, rice, maize or sorghum); sugar beets (such as sugar or fodder beets); fruits (such as bananas, pomes, stone fruits or soft drinks). fruits (such as apples, pears, plums, peaches, almonds, cherries, berries (such as strawberries, raspberries, or blackberries)); legumes (such as beans, lentils, peas, or soybeans); oil plants (such as canola , mustard, poppy, olive, sunflower, coconut, castor, cocoa, or peanut); cucurbits (such as pumpkin, cucumber, or melon); fibrous plants (such as cotton, flax, hemp, or jute); citrus fruits (such as willow oranges, lemons, grapefruit, or tangerines); vegetables (such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers); Lauraceae (such as avocado, cinnamon, or camphor); and Tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, the plantain family, latex plants, and ornamental plants (such as flowers, lawns, or turf). In one embodiment, the plant is Selected from cereals, corn, soybeans, rice, sugar cane, vegetables and oily plants.

The term "plant" is to be understood to also include plants that have been transformed by using recombinant DNA techniques, which are capable of synthesizing one or more selectively acting toxins (such as are known, for example, from toxin-producing bacteria, especially Bacillus ( genus Bacillus), as well as plants that have been selected or crossed to maintain and/or acquire desired characteristics such as insect, fungal and/or nematode resistance. Toxins expressible by such transgenic plants include, for example, : Insecticidal proteins, such as those produced by Bacillus cereus or Bacillus popilliae, or those produced by Bacillus thuringiensis, such as delta-endotoxin (delta-endotoxin) -endotoxins) such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry2A, Cry2Bbl or Cry9c; vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or bacterial colonizing nematodes Insecticidal proteins of photorhabdus spp. or Xenorhabdus spp. such as Photorhabdus luminescens and Xenorhabdus nematophilus Toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins; phytohemagglutinins, such as legumes, barley Lectins or snowdrop lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serpins, patatin, cystatin or papain (papain) inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, Saporin or bryodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase -glycosyl-transferase), cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers such as sodium or calcium channel blockers; juvenile hormone esterase ( juvenile hormone esterase); diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, it should be understood that delta-endotoxins (eg Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C) or nutritional insecticidal proteins (Vip) (eg Vipl, Vip2, Vip3 or Vip3A) are also Especially hybrid toxins, truncated toxins and modified toxins. Hybrid proteins are characterized by novel combinations of protein domains (see, eg, PCT Patent Publication No. WO 02/015701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of a modified toxin, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid substitutions, it is preferred to insert a non-naturally occurring protease recognition sequence into the toxin, such as in the case of Cry3A055, a cathepsin-G-recognition sequence into the Cry3A toxin (see WO 03/018810) . Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are also found in, for example, European Patent No. EP-A-0 374 753, PCT Patent Publication No. WO 93/007278, PCT Patent Publication No. WO 95/34656, European Patent No. EP-A-0 374 753 It is disclosed in Patent No. EP-A-0 427 529, European Patent No. EP-A-451 878 and PCT Patent Publication No. WO 03/52073. Methods of producing such genetically modified plants are generally known to those of ordinary skill in the art and are described, for example, in the aforementioned publications. Deoxyribonucleic acids of the CryI type and methods for their preparation are known, for example, from PCT Patent Publication No. WO 95/34656, European Patent No. EP-A-0 367 474, European Patent No. EP-A-0 401 979 and PCT Patent Publication No. in WO 90/13651. Toxins contained in transgenic plants confer tolerance to harmful insects. While these insects can exist in any taxonomic group of insects, beetles (Coleoptera), bipedal insects (Diptera) and butterflies (Lepidoptera) are particularly common. Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some are commercially available. Examples of these plants are: YieldGard ^® (a maize variant expressing the Cry1Ab toxin); YieldGard Rootworm ^® (a maize variant expressing the Cry3Bb1 toxin); YieldGard Plus ^® (a maize variant expressing the Cry1Ab and Cry3Bb1 toxins); Starlink ^® (a maize variant expressing the Cry9C toxin) maize variety); HerculexI ^® (maize expressing Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) for tolerance to the herbicide glufosinate-ammonium cultivar); NuCOTN 33B ^® (cotton cultivar expressing Cry1Ac toxin); Bollgard I ^® (cotton cultivar expressing Cry1Ac toxin); Bollgard II ^® (cotton cultivar expressing Cry1Ac and Cry2Ab toxin ⁾ ; cotton variety); NewLeaf ^® (potato variety expressing Cry3A toxin); NatureGard ^® , 25Agrisure ^® GT Advantage (GA21 glyphosate resistance), Agrisure ^® CB Advantage (Bt11 corn borer (CB) resistance) and Protecta ^® . Other examples of such transgenic crops are: i) Bt11 maize available from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, accession number C/FR/96/05/10 . A genetically modified maize (Zea mays) that has been transgenic to express a truncated Cry1Ab toxin against attack by European corn borers (Ostrinia nubi/alis and Sesamia nonagrioides) . Bt11 maize was also transgenic to express the enzyme PAT for tolerance to the herbicide glufosinate-ammonium; ii) Bt176 maize, available from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. A genetically modified maize that has been transgenic to express a truncated CryIAb toxin that is resistant to attack by European corn borers (C. Bt176 maize was also transgenic to express the enzyme PAT for tolerance to the herbicide glufosinate-ammonium; iii) MIR604 maize, obtained from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. A corn that has been transgenic to express a modified Cry3A toxin for resistance to insects. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of these transgenic maize plants is described in PCT Patent Publication No. WO 03/018810; iv) MON 863 maize available from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, accession number C /DE/02/9. MON863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects; v) IPC 531 cotton, available from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, accession number C/ES/96/02 ; vi) 1507 Maize available from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. A genetically modified corn expressing the protein Cry1F to obtain resistance against certain Lepidopteran insects and expressing the PAT protein to obtain tolerance to the herbicide glufosinate; vii) NK603×MON 810 corn, obtained from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. It consists of hybrid corn varieties bred according to conventional methods, which are obtained by crossing genetically modified varieties NK603 with MON 810. NK603×MON 810 maize expresses the protein CP4 EPSPS obtained from Agrobacterium sp. strain CP4 by means of transgenic gene, so as to obtain the tolerance to the herbicide Roundup (containing glyphosate), and express from Bacillus thuringiensis Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki to acquire tolerance against certain Lepidoptera, including European corn borer.

In one embodiment, the present invention provides a composition comprising a compound of formula (I), a stereoisomer, agriculturally acceptable salt, tautomer, or N-oxide thereof and one or more reactive Compatible substances, these active compatible substances are selected from fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.

The compounds of the present invention are effective in controlling nematodes and/or fungal pathogens in growing and harvested agronomic plants, and when used alone, they can also be combined with other biologically active agents used in agriculture (such as one or more nematicides, Insecticides, acaricides, fungicides, fungicides, plant activators, molluscicides, and pheromones (whether chemical or biological) are used together. Combining the compounds of the invention or compositions thereof in use form as insecticides with other insecticides generally results in a broader spectrum of insecticidal action. For example, the compounds of formula (I) of the present invention can be combined with pyrethroids, neonicotinoids, macrolides, diamides, phosphates , carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas , pyrrole, etc.

By adding, for example, one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents, the activity of the compositions of the present invention can be significantly broadened and adapted to most situations. Combinations of compounds of formula (I) with other insecticidally, acaricidally, nematicidally and/or fungicidally active compounds may also have further surprising advantages. For example, better plant tolerance, reduced phytotoxicity, and pests or fungi can be controlled at different stages of their development, or have better behavior during their production, such as during grinding or mixing, during storage or during use.

Known and reported active compounds such as fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, protectants, plant growth regulators, antibiotics, fertilizers and nutrients can be combined with Combination of at least one compound of formula I according to the invention. For example, fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, protectants, plant growth regulators, antibiotics disclosed in PCT Patent Publication No. WO2017076739 (A to O) , fertilizers and nutrients can be combined with the compounds of formula I of the present invention. The present invention also relates to such combinations comprising compounds of the present invention and active compatible compounds as reported in PCT Patent Publication No. WO2017076739.

The compounds of formula (I) of the present invention may also be combined with other pesticidally active compounds whose mode of action is unknown or uncertain, such as the following: afidopyropen, afoxolaner, azadirachtin , Amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite ( cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluorine Fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, acetamiprid Pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 11-(4-chloro-2,6-di) Methylphenyl)-12-hydroxy-1,4-dioxo-9-azabibisspiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4'-fluoro- 2,4-Dimethylben-3-yl)-4-hydroxy-8-oxo-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4- Methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1,2,4-triazole-5- Amine, Bacillus firmus; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2- Trifluoro-acetamide; (E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2 -Trifluoro-acetamide; (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-dihydropyridyl] Acetamide; (E/Z)-N-[1-[(6-Bromo-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2-trifluoroacetamide; (E/Z)-N-[1-[1-(6-Chloro-3-pyridyl)ethyl (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2 -dihydropyridyl]-2,2-difluoro-acetamide; (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2- Dihydropyridyl]-2,2-difluoro-acetamide; (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-dihydropyridyl] -2,2,2-Trifluoro-acetamide; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2, 2,3,3,3-Pentafluoro-propionamide); N-[1-[(6-Chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2- Trifluoro-thioacetamide; N-[1-[(6-Chloro-3-pyridyl)methyl]-2-dihydropyridyl]-2,2,2-trifluoro-N'-isopropyl yl-acetamide; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl ]-2-Methyl-N-(1-oxythietan-3-yl)benzamide; Fluoxamide; 5-[3-[2,6-Dichloro-4-( 3,3-Dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 3-(benzylmethylamino)-N-[2-bromo-4-[1, 2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; 3-(benzene carboxylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl) Fluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] -6-(Trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzylamine; N-[3-[[[2-bromo-4-[1,2, 2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl benzamide; 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl ]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoro-N-[2-fluoro-3-[[[2- Iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl yl-benzamide; 2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6 -(Trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-nitrile-N-[2-nitrile-5-[[2,6-dibromo- 4 -[1,2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminocarbamoyl]phenyl]-2-methyl-benzylamide; 4-cyano-3-[(4-cyano-2-methyl-benzyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3, 3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-benzamide; N-[5-[[2-chloro-6-cyano-4-[1,2, 2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminocarbamoyl]-2-nitrile-phenyl]-4-nitrile-2-methyl- Benzylamide; N-[5-[[2-Bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl] Aminocarboxy]-2-nitrile-phenyl]-4-nitrile-2-methyl-benzylamine; N-[5-[[2-bromo-6-chloro-4-[1, 2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminocarbamoyl]-2-nitrile-phenyl]-4-nitrile-2-methyl yl-benzamide; 4-nitrile-N-[2-nitrile-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1 -(Trifluoromethyl)propyl]phenyl]aminocarbamoyl]phenyl]-2-methyl-benzylamine; 4-nitrile-N-[2-nitrile-5-[[2 ,6-Dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]aminocarbamoyl]phenyl]-2-methyl-benzyl Amide; N-[5-[[2-Bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]aminocarbamoyl ]-2-nitrile-phenyl]-4-nitrile-2-methyl-benzamide; 2-(1,3-diox-2-yl)-6-[2-(3-pyridine base)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; 2-[6-[ 2-(3-Pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; N-methanesulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2 - Carboxamide; Mesylate-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2- (3-Pyridinyl)thiazol-5-yl]-3-methylthio-propionamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl] -3-Methylthio-propionamide; N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthiopropionamide ; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; N-[4-chloro -2-(3-Pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propionamide; N-[4-Chloro-2-(3-pyridyl] )thiazol-5-yl]-N,2-dimethyl-3-methyl Sulfanyl-propionamide; N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylsulfanyl-propionamide; N-[4-chloro -2-(3-Pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propionamide; 1-[(6-chloro-3-pyridyl)methyl]-1, 2,3,5,6,7-Hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridine-3 -yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; 1-isopropyl yl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1 -Methyl-ethyl)pyrazole-4-carboxyamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazine-4 -yl-pyrazole-4-carboxamide; N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole- 4-Carboxamide; 1-(1,2-Dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-[1 -(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazol-4-carboxamide; N-methyl-1-(2- Fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazol-4-carboxamide; 1-(4,4-difluorocyclohexyl)-N-ethyl 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazine -4-yl-pyrazol-4-carboxamide; N-(1-methylethyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide; N-cyclopropyl -2-(3-pyridyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; 2-(3 -Pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridyl)-N-[(tetrahydro-2-furan Methyl)methyl]-2H-indazole-5-carboxamide; 2-[[2-(3-pyridyl)-2H-indazole-5-yl]carbonyl]hydrazinecarboxylate; Methyl 2-[[2-(3-pyridyl)-2H-indazole-5-yl]carbonyl]hydrazinecarboxylate [(2,2-Difluorocyclopropyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; N-(2,2-difluoropropyl)-2 -(3-Pyridyl)-2H-indazole-5-carboxamide; 2-(3-pyridyl)N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; N -[(5-Methyl-2-pyrazinyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; N-[3-chloro-1-(3- Pyridyl)pyrazol-4-yl ]N-ethyl-3-(3,3,3-trifluoropropanesulfonyl)propionamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N -Ethyl-3-(3,3,3-trifluoropropanesulfonyl)propionamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[ (2,2-Difluorocyclopropyl)methanesulfonyl]-N-ethyl-propionamide; N-[3-chloro-1-(3-pyridyl)pyrazole-4-yl]-3 -[(2,2-Difluorocyclopropyl)methanesulfonyl]-N-ethyl-propionamide; sarolaner, lotilaner.

The above-mentioned active substances, their preparation and their activity (eg against harmful fungi/insects/nematodes) are known (see: http://www.alanwood.net/pesticides/); these substances are commercially available purchased. Compounds described under IUPAC nomenclature, their preparation and their pesticidal activity are also known (see 0366 > Can. J. Plant Sci. 48(6), 587-94, 1968; European Patent No. EP-A 141 317; European Patent No. EP-A 152 031; European Patent No. EP-A 226 917; European Patent No. EP-A 243 970; European Patent No. EP-A 256 503; European Patent No. EP-A 428 941; European Patent No. No. EP-A 532 022; European Patent No. EP-A 1 028 125; European Patent No. EP-A1 035 122; European Patent No. EP-A 1 201 648; European Patent No. EP-A 1 122 244; Japanese Patent No. JP 2002316902; German Patent No. DE 19650197; German Patent No. DE 10021412; National Patent No. DE 102005009458; US Patent No. US 3,296,272; US Patent No. US 3,325,503; ; PCT Patent Publication No. WO 99/24413; PCT Patent Publication No. WO 99/27783; PCT Patent Publication No. WO 00/29404; PCT Patent Publication No. WO 00/46148; PCT Patent Publication No. WO 00/65913; WO 01/54501; PCT Patent Publication No. WO 01/56358; PCT Patent Publication No. WO 02/22583; PCT Patent Publication No. WO 02/40431; PCT Patent Publication No. WO 03/10149; PCT Patent Publication No. WO 03/11853; PCT Patent Publication No. WO 03/14103; PCT Patent Publication No. WO 03/16286; PCT Patent Publication No. WO 03/53145; PCT Patent Publication No. WO 03/61388; PCT Patent Publication No. WO 03/66609; PCT Patent Publication No. WO 03/74491; PCT Patent Publication No. WO 04/49804; PCT Patent Publication No. WO 04/83193; PCT Patent Publication No. WO 05/120234; PCT Patent Publication No. WO 05/123689; PCT Patent Publication No. WO 05/123690; Patent Publication No. WO 05/63721; PCT Patent Publication No. WO 05/87772; PCT Patent Publication No. WO 05/87773; PCT Patent Publication No. WO 06/15866; PCT Patent Publication No. WO 06/87325; PCT Patent Publication No. WO 06 /87343 PCT Patent Publication No. WO 07/82098; PCT Patent Publication No. WO 07/90624; PCT Patent Publication No. WO 10/139271; PCT Patent Publication No. WO 11/028657; PCT Patent Publication No. WO 12/168188; WO 07/006670; PCT Patent Publication No. WO 11/77514; PCT Patent Publication No. WO 13/047749; PCT Patent Publication No. WO 10/069882; PCT Patent Publication No. WO 13/047441; PCT Patent Publication No. WO 03/16303; PCT Patent Publication No. WO 09/90181; PCT Patent Publication No. WO 13/007767; PCT Patent Publication No. WO 13/010862; PCT Patent Publication No. WO 13/127704; PCT Patent Publication No. WO 13/024009; PCT Patent Publication No. WO 13/24010; PCT Patent Publication No. WO 13/047441; PCT Patent Publication No. WO 13/162072; PCT Patent Publication No. WO 13/092224; PCT Patent Publication No. WO 11/135833; Chinese Patent No. CN 1907024; Chinese Patent No. CN 1456054; Chinese Patent No. CN 103387541; Chinese Patent No. CN 1309897; PCT Patent Publication No. WO 12/84812; Chinese Patent No. CN 1907024; PCT Patent Publication No. WO 09094442; PCT Patent Publication No. WO 14/60177; PCT Patent Publication No. WO 13/116251; PCT Patent Publication No. WO 08/013622; PCT Patent Publication No. WO 15/65922; PCT Patent Publication No. WO 94/01546; European Patent No. EP 2865265; PCT Patent Publication No. WO 07/129454; PCT Patent Publication No. WO 12/165511; PCT Patent Publication No. WO 11/081174; PCT Patent Publication No. WO 13/47441).

The mass ratio of any two ingredients in each combination is chosen to provide the desired effect, such as enhanced activity. In general, mass ratios will vary depending on the particular ingredients and the amount of ingredients present in the combination. In general, the mass ratio between any two components in any combination of the present invention is independently of each other from 100:1 to 1:100, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83: 17, 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58: 42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:48, 51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61, 38:62, 37:63, 36:64, 35:65, 34:66, 33: 67, 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8: 92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98 to 1:99. The mass ratio between the two components of the present invention is preferably from 75:1 to 1:75, particularly preferably 50:1 to 1.50, particularly preferably 25:1 to 1:25, advantageously 10:1 1 to 1:10, eg 5:1 to 1:5, eg 1:3 to 3:1. Mixing ratios are understood to include mass ratios on the one hand and molar ratios on the other hand.

A combination of the present invention (ie, a combination comprising a compound of the present invention and one or more other biologically active agents) can be administered simultaneously or sequentially.

Where the components of the combination are administered sequentially (ie, one after the other), the components are administered sequentially within a reasonable time of each other (eg, within hours or days) to achieve biological performance. The order in which the ingredients are administered in combination, ie whether the compound of formula (I) should be administered first, is not critical to the practice of the present invention.

If the components of the combination are administered simultaneously in the present invention, they may be administered as a composition comprising the composition, in which case: (A) the compound of formula (I) and one or more other components of the combination may be prepared from separate formulations Sources are obtained and mixed together (called tank-mix, ready-to-apply, spray broth or slurry), or (B) a compound of formula (I) and one or more other The ingredients may be obtained as a source of a single formulation mixture known as a pre-mix, ready-mix, concentrate or formulated product.

In one embodiment, independent of the other embodiments, the compounds according to the present invention are applied as compositions. Accordingly, the present invention also provides a composition comprising the compound of the present invention described herein and one or more other biologically active agents and optionally one or more general formulation adjuvants; it can be tank-mixed or Presented in the form of ready-mixed compositions.

The compounds of formula (I) are particularly useful for the control and prevention of infestation and infection of warm-blooded animals such as cattle, sheep, pigs, camels, deer by endogenous (endo) and exogenous (ecto) parasites of helminths and nematodes , horses, poultry, fish, rabbits, goats, minks, foxes, chinchillas, dogs and cats, and humans. For the control and prevention of infestation and infection in warm-blooded animals, the compounds of the present invention are particularly useful for the control of helminths and nematodes. Examples of worms are members of the class Trematoda, commonly known as flukes or flatworms, especially Fasciola, Fascioloides , Paramphistomu, Dicrocoelium, Eurytrema, Opisthorchis, Fasciolopsis, Acanthostomy (Echinostoma) and Paragonimus. Nematodes that can be controlled by compounds of formula (I) include Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria, etc. For oral administration to warm-blooded animals, the compounds of the present invention can be formulated into animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, infusions, gels, tablets, pills and capsules. In addition, the compounds of the present invention can be administered to animals through drinking water. For oral administration, the dosage form selected should provide the animal with about 0.01 mg/kg to 100 g/kg of the animal's body weight per day of the compound of the invention. Alternatively, the compounds of the present invention may be administered parenterally, for example by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention can be formulated into implants for subcutaneous administration. In addition, the compounds of the present invention can be administered transdermally to animals. For parenteral administration, the dosage form selected should provide the animal with about 0.01 mg/kg to 100 g/kg of the animal's body weight per day of a compound of the invention.

The compounds of the present invention can also be administered topically to animals in the form of infusions, dusts, powders, collars, medallions, sprays and pour-on formulations. For topical application, dips and sprays typically contain from 0.5 ppm to 5,000 ppm, and preferably from about 1 ppm to 3,000 ppm, of a compound of the present invention. Furthermore, the compounds of the present invention can be formulated into ear tags for animals, particularly quadrupeds such as cattle and sheep.

In one embodiment, independent of other embodiments, the compound of formula (I) is an antihelminthic compound.

In one embodiment, independent of other embodiments, the compound of formula (I) is a pesticidal compound, preferably a nematicidal compound.

The compounds of the present invention are not only effective in controlling nematode pests, but also exhibit positive crop responses (e.g. plant growth promoting effects such as enhanced crop vigor, enhanced root growth, enhanced response to drought, high salt, high temperature, cold, frost or light radiation tolerance, improved flowering, efficient water and nutrient use (e.g. improved nitrogen assimilation), improved plant product quality, more tillers, increased resistance to fungi, insects, pests, etc.), thereby Increase production.

Chemical example:

The following examples illustrate, but are not limited to, means and procedures for the preparation of the compounds of this invention, and include the best modes contemplated by the inventors for carrying out the invention.

Example 1 : 4,4 -Difluorobut - 3 -en- 1 - yl 2- (4- chloro -1H- pyrazol- 1 -yl ) acetate (4,4-difluorobut-3-en-1-yl ) Preparation of 2-(4-chloro-1H-pyrazol-1-yl)acetate )

To a solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (250 mg, 1.56 mmol) in dry N,N-dimethylformamide (8 mL) was added N,N-dimethylformamide (8 mL). N-diisopropylethylamine (0.27 ml, 1.56 mmol) and 4-bromo-1,1-difluorobut-1-ene (532 mg, 3.11 mmol), and the reaction mixture was stirred at 80 °C for 16 h . After that, it was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 4,4-difluorobut-3-en-1-yl 2-(4-chloro- 1H-pyrazol-1-yl)acetate (270 mg, 1.077 mmol, 69.2 % yield), LCMS (M+1): 251

Example 2 : 3,4,4 -Trifluorobut- 3 -en- 1 -yl 2-(4- methyl -1H- pyrazol- 1 -yl ) acetate (3,4,4-trifluorobut-3- Preparation of en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate )

To a solution of 2-(4-methyl-1H-pyrazol-1-yl)acetic acid (450 mg, 3.21 mmol) in dry N,N-dimethylformamide (8 mL) was added N , N-diisopropylethylamine (0.561 ml, 3.21 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (928 mg, 6.42 mmol), and the reaction mixture was kept at 80 °C Stir for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl) yl-1H-pyrazol-1-yl)acetate (375 mg, 1.51 mmol, 47.1 % yield), LCMS (M+1): 249.1

Example 3 : 3,4,4 -Trifluorobut- 3 -en- 1 -yl 2-(3,5 -dimethyl -1H- pyrazol- 1 -yl ) acetate (3,4,4-trifluorobut -The preparation method of 3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate)

In a solution of 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetic acid (450 mg, 2.92 mmol) in dry N,N-dimethylformamide (8 mL) N,N-Diisopropylethylamine (0.510 ml, 2.92 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (844 mg, 5.84 mmol) were added and the reaction mixture was at Stir at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(3,5 -Dimethyl-1H-pyrazol-1-yl)acetate (340 mg, 1.297 mmol, 44.4 % yield), LCMS (M+1): 263.1

Example 4 : 3,4,4 -Trifluorobut- 3 -en- 1 -yl 2-(4- chloro -1H- pyrazol- 1 -yl ) propanoate (3,4,4-trifluorobut-3- Preparation of en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate )

step 1 : 2-(4- chlorine -1H- Pyrazole -1- base ) Ethyl propionate (ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate) preparation

To a solution of 4-chloro-1H-pyrazole (500 mg, 4.88 mmol) in dry N,N-dimethylformamide (10 mL) was added potassium carbonate (1.35 g, 9.75 mmol) and 2- Ethyl bromopropionate (0.9 ml, 6.4 mmol), and the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound, ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate (600 mg , 2.96 mmol, 60.7% yield), LCMS (M+1): 203.1

step 2 : 2-(4- chlorine -1H- Pyrazole -1- base ) propionic acid (2-(4-chloro-1H-pyrazol-1-yl)propanoic acid) preparation

To a solution of 2-(4-chloro-1H-pyrazol-1-yl)propanoate (1 g, 4.93 mmol) in methanol-tetrahydrofuran (6 ml:3 ml) was added lithium hydroxide (0.236 g, 9.87 mmol) in water (1 ml) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(4-chloro-1H-pyrazol-1-yl)propionic acid (600 mg, 3.44 mmol, yield 69.6 %), LCMS (M+1): 174.9

step 3 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(4- chlorine -1H- Pyrazole -1- base ) propionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate) preparation

To a solution of 2-(4-chloro-1H-pyrazol-1-yl)propionic acid (400 mg, 2.291 mmol) in dry N,N-dimethylformamide (8 mL) was added N , N-diisopropylethylamine (0.8 ml, 4.58 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (662 mg, 4.58 mmol), the reaction mixture was stirred at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro -1H-pyrazol-1-yl)propionate (500 mg, 1.77 mmol, 77 % yield), LCMS (M+1): 282.95

Example 5 : 3,4,4 -Trifluorobut- 3 -en- 1 -yl 2-(4- chloro -1H- pyrazol- 1 -yl )-2 -methylpropanoate (3,4,4 - Preparation of trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate )

step 1 : 2-(4- chlorine -1H- Pyrazole -1- base )-2- Ethyl methylpropionate (ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) preparation

To a solution of 4-chloro-1H-pyrazole (500 mg, 4.88 mmol) in dry N,N-dimethylformamide (10 mL) was added cesium carbonate (9.53 g, 29.3 mmol) and 2 -Bromo-2-methylpropionic acid ethyl ester (2.85 ml, 19.02 mmol), and the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid Ethyl ester (2.5 g, 11.54 mmol, 79 % yield), LCMS (M+1): 217.1

step 2 : 2-(4- chlorine -1H- Pyrazole -1- base )-2- Methylpropionic acid (2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoic acid) preparation

To a solution of 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid ethyl ester (3 g, 13.85 mmol) in methanol-tetrahydrofuran (6 ml:3 ml) was added hydrogen Lithium oxide (0.66 g, 27.7 mmol) in water (1 ml) was dissolved, and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid (2 g, 10.6 mmol, 77% yield), LCMS (M+1): 189.1

step 3 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(4- chlorine -1H- Pyrazole -1- base )-2- Methylpropionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) preparation

A solution of 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid (300 mg, 1.59 mmol) in dry N,N-dimethylformamide (8 mL) , N,N-diisopropylethylamine (0.6 ml, 3.2 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (460 mg, 3.18 mmol) were added, and the reaction mixture was Stir at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography using 1-30% ethyl acetate/hexane to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro -1H-pyrazol-1-yl)-2-methylpropionate (420 mg, 1.42 mmol, 89 % yield), LCMS (M+1): 296.95

Example 6 : 3,4,4 -Trifluorobut- 3 -en- 1 -yl 2-(4- methyl -1H- pyrazol- 1 -yl ) propionate (3,4,4-trifluorobut-3 Preparation of -en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate )

step 1 : 2-(4- methyl -1H- Pyrazole -1- base ) Ethyl propionate (ethyl 2-(4-methyl-1H-pyrazol-1-yl)propanoate) preparation

To a solution of 4-methyl-1H-pyrazole (1.5 g, 18.27 mmol) in dry N,N-dimethylformamide (10 mL) was added potassium carbonate (5.05 g, 36.5 mmol) and 2 - Ethyl bromopropionate (3.31 ml, 23.75 mmol), the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionic acid Ethyl ester (2.5 g, 11.54 mmol, 79 % yield), LCMS (M+1): 217.1

step 2 : 2-(4- methyl -1H- Pyrazole -1- base ) propionic acid (2-(4-methyl-1H-pyrazol-1-yl)propanoic acid) preparation

Lithium hydroxide ( 0.58 g, 24.2 mmol) in water (1 ml), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(4-methyl-1H-pyrazol-1-yl)propionic acid (1.5 g, 9.73 mmol, yield 81 %), LCMS (M+1): 155.1

step 3 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(4- methyl -1H- Pyrazole -1- base ) propionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate) preparation

To a solution of 2-(4-methyl-1H-pyrazol-1-yl)propionic acid (300 mg, 1.95 mmol) in dry N,N-dimethylformamide (8 mL) was added N,N-diisopropylethylamine (0.68 ml, 3.89 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (366 mg, 2.53 mmol), and the reaction mixture was kept at 80 °C Stir for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl) yl-1H-pyrazol-1-yl)propionate (345 mg, 1.32 mmol, 67.6 % yield), LCMS (M+1): 263.1

Example 7 : 3,4,4 -Trifluorobut- 3 -en- 1 -yl 2- methyl -2-(4- methyl -1H- pyrazol- 1 -yl ) propionate (3,4, Preparation of 4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate )

step 1 : 2- methyl -2-(4- methyl -1H- Pyrazole -1- base ) Ethyl propionate (ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate) preparation

To a solution of 4-methyl-1H-pyrazole (1.5 g, 18.27 mmol) in dry N,N-dimethylformamide (10 mL) was added cesium carbonate (8.93 g, 27.4 mmol) and Ethyl 2-bromo-2-methylpropanoate (4.63 g, 23.75 mmol), the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propane Ethyl acid (2.1 g, 10.70 mmol, 58.6 % yield) LCMS (M+1): 197.1

step 2 : 2- methyl -2-(4- methyl -1H- Pyrazole -1- base ) propionic acid (2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoic acid) preparation

In a solution of ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate (2.5 g, 12.74 mmol) in methanol-tetrahydrofuran (6 ml:3 ml) A solution of lithium hydroxide (0.61 g, 25.5 mmol) in water (1 ml) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the desired product, 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionic acid (1.8 g , 10.7 mmol, 84% yield), LCMS (M+1): 169.1

step 3 : 3,4,4- trifluorobutane -3- alkene -1- base 2- methyl -2-(4- methyl -1H- Pyrazole -1- base ) propionate (3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate)

A solution of 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionic acid (600 mg, 3.57 mmol) in dry N,N-dimethylformamide (8 mL) To the solution, N,N-diisopropylethylamine (1.2 ml, 7.13 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (670 mg, 4.64 mmol) were added and reacted The mixture was stirred at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl2-methyl-2 -(4-Methyl-1H-pyrazol-1-yl)propionate (350 mg, 1.267 mmol, 35.5 % yield), LCMS (M+1): 277.1

Example 8 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(3- methyl -1H- Indazole -1- base ) Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate) preparation

step 1 : 2-(3- methyl -1H- Indazole -1- base ) Ethyl acetate (ethyl 2-(3-methyl-1H-indazol-1-yl)acetate) preparation

To a solution of 3-methyl-2H-indazole (400 mg, 3.03 mmol) in dry acetone (8 mL) was added potassium carbonate (837 mg, 6.05 mmol) and ethyl 2-bromoacetate (505 mg, 3.03 mmol), and the reaction mixture was stirred at 60 °C for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound, ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (500 mg , 2.3 mmol, 76% yield) LCMS (M+1): 219.1

step 2 : 2-(3- methyl -1H- Indazole -1- base ) acetic acid (2-(3-methyl-1H-indazol-1-yl)acetic acid) preparation

To a solution of ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (590 mg, 2.70 mmol) in methanol-tetrahydrofuran (4 ml:2 ml) was added lithium hydroxide (129 mg , 5.41 mmol) in water (0.5 ml), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (60 ml x 2). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired product, 2-(3-methyl-1H-indazol-1-yl)acetic acid (450 mg, 2.37 mmol, yield 88 %), LCMS (M+1): 191.1

step 3 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(3- methyl -1H- Indazole -1- base ) Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate) preparation

To a solution of 2-(3-methyl-2H-indazol-2-yl)acetic acid (250 mg, 1.314 mmol) in dry N,N-dimethylformamide (7 mL) was added N,N-dimethylformamide (7 mL). N-diisopropylethylamine (0.46 ml, 2.63 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (247 mg, 1.71 mmol), the reaction mixture was stirred at 80 °C for 16 h . The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl) yl-2H-indazol-2-yl)acetate (160 mg, 0.54 mmol, 40 % yield), LCMS (M+1): 299.3

Example 9 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(4,5- Dichloro -1H- imidazole -1- base ) Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate) preparation

step 1 : 2-(4,5- Dichloro -1H- imidazole -1- base ) acetic acid (2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid) preparation

To a solution of 4,5-dichloro-1H-imidazole (1 g, 7.30 mmol) in dry acetonitrile (20 ml) was added potassium carbonate (1.514 g, 10.95 mmol) and tert-butyl 2-bromoacetate (1.295 ml, 8.76 mmol), the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the desired product, tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 g) mmol, 98% yield). To a stirred solution of tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 mmol) in dichloromethane (10 ml) was added hydrochloric acid (7.17 ml, 28.7 mmol) and stirred at 20-25 °C for 16 h. The reaction mixture was evaporated to dryness to give the desired product 2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid, 1.5 g, as an off-white solid (hydrochloride). LCMS (M+1): 194.80; ¹ HNMR: ¹ H-NMR (400 MHz, DMSO-d6 ) δ 9.57-9.79 (br s, 1H), 7.78 (s, 1H), 4.87 (s, 2H)

step 2 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(4,5- Dichloro -1H- imidazole -1- base ) Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate) preparation

To a solution of 2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid (1.5 g, 7.69 mmol) in dry N,N-dimethylformamide (10 mL) was added N , N-diisopropylethylamine (4.03 ml, 23.1 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (247 mg, 1.71 mmol), the reaction mixture was stirred at 80 °C for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flushing system to obtain the target compound 3,4,4-trifluorobut-3-en-1-yl 2-(4,5 -Dichloro-1H-imidazol-1-yl)acetate (1.1 g, 3.63 mmol, 47.2 % yield) as dark brown oil, LCMS (M-1): 302.85

example 10 : 3,4,4- trifluorobutane -3- alkene -1- base 2-(3,5- dimethyl -1H-1,2,4- triazole -1- base ) Acetate (3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate) preparation

Dry N,N-dimethylformamide (05) in 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetic acid (300 mg, 1.94 mmol) mL), was added N,N-diisopropylethylamine (1.013 ml, 5.80 mmol) and 4-chloro-1,1,2-trifluorobut-1-ene (419 mg, 2.90 mmol) , and the reaction mixture was stirred at 80 °C for 12 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound, 3,4,4-trifluorobut-3-en-1-yl 2-(3, 5-Dimethyl-1H-1,2,4-triazol-1-yl)acetate, LCMS (M+1): 263.9

example 11 : 2-(4- chlorine -1H- Pyrazole -1- base )-N-(3,4,4- trifluorobutane -3- alkene -1- base ) Acetamide (2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl)acetamide) preparation

To a stirred solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (0.179 g, 1.114 mmol) in N,N-dimethylformamide (3 ml) was added 3 ,4,4-trifluorobut-3-en-1-amine hydrochloride (0.150 g, 0.928 mmol) and N,N-diisopropylethylamine (0.487 ml, 2.79 mmol) and then HATU (0.530 g, 1.393 mmol). The resulting reaction mixture was stirred at 25 °C for 3 h. The reaction mixture was then diluted with water and extracted with ethyl acetate (25ml x 2). The organic layer was dried over anhydrous sodium sulfate, and concentrated and dried under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as a flush system to give the title compound 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4 ,4-Trifluorobut-3-en-1-yl)acetamide (170 mg, 0.635 mmol, 68.4 % yield) as a colorless oil. LCMS (M+1): 267.8

surface 1 Representative compounds of the invention were prepared according to suitable methods described in the Schemes and Examples

Table 1: Compound number IUPAC name Spectral data 1 4,4-Difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (4,4-difluorobut- 3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.34 (s, 1H), 4.90 (s, 2H), 4.08-4.20 (m, 3H), 2.30-2.36 (m, 2H), 2.29 (d, J = 0.7 Hz, 3H); LCMS (M+1): 298.75 2 4,4-Difluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3- en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.96 (s, 1H), 5.09 (s, 2H), 4.20 (td, J = 6.4, 0.6 Hz, 2H), 4.10 (dtd, J = 24.7, 7.9, 2.0 Hz, 1H), 2.29-2.35 (m, 2H); LCMS (M-1): 350.95 3 4,4-Difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3-en-1- yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.81 (s, 1H), 4.87 (s, 2H), 4.48 (dtd, J = 26.8, 7.8, 2.6 Hz, 1H), 4.10 (td, J = 6.4, 0.7 Hz, 2H), 2.23-2.29 (m, 2H), 2.12 (d, J = 0.7 Hz, 3H), 2.05 (s, 3H); LCMS (M+1): 245.15 4 4,4-Difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2- (4-methyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.37 (s, 1H), 7.25 (d, J = 12.0 Hz, 2H), 4.87 (s, 2H), 4.13-4.20 (m, 2H), 2.30-2.36 (m, 2H), 2.04-2.09 (m, 3H); LCMS (M+1): 231 5 4,4-Difluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3- en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.86 (d, J = 40.7 Hz, 1H), 6.67-6.77 (m, 1H), 6.58 (d, J = 42.2 Hz, 1H), 5.06 (s, 2H) ), 4.14-4.21 (m, 2H), 4.10 (td, J = 7.9, 2.0 Hz, 1H), 2.30-2.36 (m, 2H); LCMS (M-1): 314.95 6 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (3,4, 4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.34 (s, 1H), 4.91 (s, 2H), 4.34 (t, J = 6.3 Hz, 2H), 2.59-2.69 (m, 2H), 2.26-2.31 (m, 3H); LCMS (M+1): 316.70 7 4,4-Difluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (4,4-difluorobut -3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.17 (s, 1H), 5.03 (s, 2H), 4.08-4.20 (m, 3H), 2.30-2.36 (m, 2H), 1.63-1.70 (m, 1H), 0.98-1.03 (m, 2H), 0.70-0.74 (m, 2H); LCMS (M+1): 325.05 8 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2-( 4-chloro-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.47 (d, J = 2.8 Hz, 2H), 4.87 (s, 2H), 4.16-4.20 (m, 2H), 4.12 (td, J = 7.9, 2.0 Hz , 1H), 2.31-2.37 (m, 2H); LCMS (M+1): 250 9 3,4,4-Trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (3,4 ,4-trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.17 (s, 1H), 5.02 (d, J = 15.0 Hz, 2H), 4.35 (t, J = 6.3 Hz, 2H), 2.59-2.69 (m, 2H) ), 1.62-1.68 (m, 1H), 0.98-1.07 (m, 2H), 0.69-0.77 (m, 2H); LCMS (M+1): 343 10 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1- yl 2-(4-chloro-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.48 (s, 1H), 7.46 (s, 1H), 4.88 (s, 2H), 4.34 (t, J = 6.3 Hz, 2H), 2.60-2.70, ( m, 2H); LCMS (M+1): 269 11 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3- en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 5.86 (s, 1H), 4.78 (s, 2H), 4.32 (t, J = 6.3 Hz, 2H), 2.58-2.68 (m, 2H), 2.23 (d , J = 15.3 Hz, 3H), 2.19 (s, 3H); LCMS (M+1): 263.05 12 3,4,4-Trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1 -yl 2-(4-methyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.36 (s, 1H), 7.22 (s, 1H), 4.87 (s, 2H), 4.32 (t, J = 6.3 Hz, 2H), 2.58-2.68 (m , 2H), 2.09 (s, 3H); LCMS (M+1): 249.10 13 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate (3,4,4- trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 6.96 (s, 1H), 5.11 (s, 2H), 4.35 (t, J = 6.3 Hz, 2H), 2.57-2.67 (m, 2H); LCMS (M -1): 368.95 14 4,4-Difluorobut-3-en-1-yl 2-(1H-indazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2-(1H-indazol- 1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.10 (d, J = 1.0 Hz, 1H), 7.77 (dt, J = 8.2, 1.0 Hz, 1H), 7.62 (dd, J = 8.4, 0.9 Hz, 1H) ), 7.37-7.41 (m, 1H), 7.13-7.17 (m, 1H), 5.39 (s, 2H), 4.42 (dtd, J = 26.7, 7.8, 2.7 Hz, 1H), 4.10 (dd, J = 6.6 , 6.1 Hz, 2H), 2.20-2.26 (m, 2H); LCMS (M+1): 267 15 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-indazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1-yl 2-( 1H-indazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.10 (d, J = 0.7 Hz, 1H), 7.77 (dt, J = 8.1, 1.0 Hz, 1H), 7.61 (dd, J = 8.4, 0.9 Hz, 1H) ), 7.36-7.40 (m, 1H), 7.13-7.17 (m, 1H), 5.40 (s, 2H), 4.23 (dd, J = 11.6, 5.5 Hz, 2H), 2.59-2.69 (m, 2H); LCMS (M+1): 285 16 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3-en-1 -yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.07 (d, J = 0.6 Hz, 1H), 7.55 (d, J = 0.6 Hz, 1H), 5.26 (q, J = 7.2 Hz, 1H), 4.17- 4.26 (m, 2H), 2.58-2.68 (m, 2H), 1.64 (d, J = 7.0 Hz, 3H); LCMS (M+1): 282.95 17 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3-en-1-yl 2- (4-chloro-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.08 (d, J = 0.6 Hz, 1H), 7.56 (d, J = 0.6 Hz, 1H), 5.24 (q, J = 7.2 Hz, 1H), 4.40 ( dtd, J = 26.6, 7.9, 2.5 Hz, 1H), 4.05-4.10 (m, 2H), 2.19-2.25 (m, 2H), 1.64 (d, J = 7.0 Hz, 3H); LCMS (M+1) : 264.95 18 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate (3,4,4-trifluorobut- 3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.17 (d, J = 0.5 Hz, 1H), 7.55 (d, J = 0.5 Hz, 1H), 4.19 (t, J = 5.7 Hz, 2H), 2.55- 2.65 (m, 2H), 1.73 (s, 6H); LCMS (M-1): 288.95 19 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionate (4,4-difluorobut-3-en- 1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.17 (d, J = 0.7 Hz, 1H), 7.56 (d, J = 0.7 Hz, 1H), 4.36 (dtd, J = 26.5, 7.9, 2.6 Hz, 1H ), 4.05 (td, J = 6.2, 0.9 Hz, 2H), 2.15-2.21 (m, 2H), 1.73 (s, 6H); LCMS (M+1): 278.95 20 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate (3,4,4- trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.94-4.98 (m, 2H), 4.25 (t, J = 6.0 Hz, 2H), 2.62-2.72 (m, 2H), 2.13 (d, J = 3.4 Hz , 3H), 2.08 (d, J = 9.2 Hz, 3H); LCMS (M+1): 296.95 twenty one 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3- en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.97 (s, 2H), 4.48 (dtd, J = 26.7, 7.8, 2.4 Hz, 1H), 4.11 (dd, J = 6.4, 5.6 Hz, 2H), 2.23 -2.29 (m, 2H), 2.13 (s, 3H), 2.07 (s, 3H); LCMS (M+1): 279.05 twenty two 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3 -en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propanoate) (3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl- 1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.80-7.83 (m, 2H), 7.47-7.54 (m, 5H), 7.38-7.42 (m, 2H), 7.31 (td, J = 7.3, 1.4 Hz, 1H), 6.85 (s, 1H), 5.18 (q, J = 6.9 Hz, 1H), 4.18 (t, J = 5.8 Hz, 2H), 2.53-2.62 (m, 2H), 1.70 (d, J = 6.7 Hz, 3H); LCMS (M+1): 401.10 twenty three 4,4-Difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3-en-1 -yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.81-7.83 (m, 2H), 7.47-7.55 (m, 5H), 7.40 (t, J = 7.3 Hz, 2H), 7.29-7.33 (m, 1H) , 6.87 (s, 1H), 5.17 (q, J = 6.9 Hz, 1H), 4.29 (dtd, J = 26.7, 7.8, 2.4 Hz, 1H), 4.03 (qd, J = 10.7, 6.0 Hz, 2H), 2.15 (q, J = 6.7 Hz, 2H), 1.70 (d, J = 7.3 Hz, 3H); LCMS (M+1): 383.10 twenty four 3,4,4-Trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3-en- 1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.53 (t, J = 0.8 Hz, 1H), 7.23 (s, 1H), 5.16 (q, J = 7.3 Hz, 1H), 4.20 (t, J = 6.0 Hz, 2H), 2.57-2.67 (m, 2H), 1.99 (s, 3H), 1.60 (d, J = 7.0 Hz, 3H), LCMS (M+1): 263.05 25 4,4-Difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3-en-1-yl 2 -(4-methyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.54 (s, 1H), 7.24 (s, 1H), 5.14 (q, J = 7.2 Hz, 1H), 4.39 (dtd, J = 26.6, 7.9, 2.6 Hz , 1H), 4.05 (t, J = 6.3 Hz, 2H), 2.17-2.23 (m, 2H), 1.99 (s, 3H), 1.60 (d, J = 7.3 Hz, 3H); LCMS (M+1) : 245.05 26 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut -3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.61 (t, J = 0.8 Hz, 1H), 7.24 (s, 1H), 4.17 (t, J = 5.8 Hz, 2H), 2.54-2.64 (m, 2H) ), 1.98 (d, J = 12.2 Hz, 3H), 1.69 (s, 6H); LCMS (M+1): 277.05 27 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3-en) -1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.62 (t, J = 0.8 Hz, 1H), 7.25 (s, 1H), 4.34 (dtd, J = 26.6, 7.9, 2.5 Hz, 1H), 4.02 (td , J = 6.2, 0.8 Hz, 2H), 2.14-2.20 (m, 2H), 2.00 (s, 3H), 1.70 (s, 6H); LCMS (M+1): 259.05 28 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3- en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.82-7.84 (m, 2H), 7.45-7.52 (m, 5H), 7.42 (td, J = 6.7, 1.4 Hz, 2H), 7.30-7.34 (m, 1H), 6.93 (s, 1H), 5.08 (s, 2H), 4.21-4.25 (m, 2H), 2.59-2.68 (m, 2H); LCMS (M+1): 387.15 29 4,4-Difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3-en-1- yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.83 (dt, J = 8.3, 1.5 Hz, 2H), 7.45-7.53 (m, 5H), 7.42 (td, J = 6.7, 1.4 Hz, 2H), 7.30 -7.34 (m, 1H), 6.93 (s, 1H), 5.08 (s, 2H), 4.42 (dtd, J = 26.6, 7.8, 2.5 Hz, 1H), 4.08 (t, J = 6.1 Hz, 2H), 2.20 (ddt, J = 14.2, 6.3, 1.7 Hz, 2H); LCMS (M+1): 369.10 30 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate (3,4,4-trifluorobut-3 -en-1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.85 (d, J = 7.9 Hz, 1H), 7.75-7.72 (m, 1H), 7.53-7.48 (m, 1H), 7.47-7.20 (m, 2H) , 5.51 (s, 2H), 4.25 (t, J = 5.8 Hz, 2H), 2.69-2.59 (m, 2H); LCMS (M+1): 335.05 31 3,4,4-Trifluorobut-3-en-1-yl 2-(3-methyl-2H-indazol-2-yl)acetate (3,4,4-trifluorobut-3-en-1 -yl 2-(3-methyl-2H-indazol-2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.70 (dt, J = 8.1, 1.0 Hz, 1H), 7.53 (dt, J = 8.6, 0.9 Hz, 1H), 7.34-7.38 (m, 1H), 7.10 -7.14 (m, 1H), 5.29 (s, 2H), 4.23 (t, J = 6.0 Hz, 2H), 2.58-2.68 (m, 2H), 2.47 (d, J = 3.2 Hz, 3H); LCMS ( M+1): 299.30 32 4,4-Difluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2- (3-methyl-1H-indazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.71 (dt, J = 7.9, 0.9 Hz, 1H), 7.53-7.55 (m, 1H), 7.34-7.38 (m, 1H), 7.10-7.14 (m, 1H), 5.28 (s, 2H), 4.42 (dtd, J = 26.6, 7.8, 2.6 Hz, 1H), 4.08 (dd, J = 6.7, 6.1 Hz, 2H), 2.46 (s, 3H), 2.20-2.26 (m, 2H); LCMS (M+1): 281.10 33 4,4-Difluorobut-3-en-1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate (4,4-difluorobut-3-en-1 -yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.85 (d, J = 8.3 Hz, 1H), 7.75 (dd, J = 8.6, 0.9 Hz, 1H), 7.53-7.49 (m, 1H), 7.48-7.21 (m, 2H), 5.50 (s, 2H), 4.43 (dtd, J = 26.6, 7.8, 2.5 Hz, 1H), 4.13-4.10 (m, 2H), 2.29-2.20 (m, 2H); LCMS (M +1): 316.95 34 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate (3,4,4- trifluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.89-7.42 (m, 3H), 5.29 (s, 2H), 4.26 (t, J = 6.0 Hz, 2H), 2.60-2.71 (m, 2H); LCMS (M-1): 332.75 35 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1-yl 2-( 1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.71 (dd, J = 2.2, 0.8 Hz, 1H), 7.45 (dd, J = 2.2, 0.8 Hz, 1H), 6.26 (t, J = 2.2 Hz, 1H) ), 5.08 (s, 2H), 4.25 (t, J = 6.0 Hz, 2H), 2.62-2.72 (m, 2H); LCMS (M+1): 235.1 36 4,4-Difluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2-(1H-pyrazol- 1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.72 (q, J = 1.0 Hz, 1H), 7.55-7.42 (m, 1H), 6.27 (t, J = 2.1 Hz, 1H), 5.07 (s, 2H) ), 4.65-4.42 (m, 1H), 4.12-3.82 (t, J = 5.6 Hz, 2H), 2.28-2.22 (m, 2H); LCMS (M+1): 216.0 37 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3 -en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.96-7.98 (q, J = 1.1 Hz, 1H), 6.75 (dd, J = 2.4, 0.5 Hz, 1H), 5.24 (s, 2H), 4.26 (t , J = 6.0 Hz, 2H), 2.62-2.72 (m, 2H); LCMS (M+1): 302.8 38 4,4-Difluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3-en-1 -yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.96-7.98 (m, 1H), 6.75 (d, J = 2.4 Hz, 1H), 5.22 (s, 2H), 4.48 (dtd, J = 26.7, 7.8, 2.5 Hz, 1H), 4.09-4.14 (m, 2H), 2.23-2.29 (m, 2H); LCMS (M+1): 284 39 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate (3,4 ,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.50 (s, 1H), 5.41 (q, J = 7.1 Hz, 1H), 4.21 (dq, J = 21.8, 5.7 Hz, 2H), 2.55-2.65 (m , 2H), 2.28 (d, J = 0.7 Hz, 3H), 1.65 (d, J = 7.1 Hz, 3H); LCMS (M+1): 330.90 40 4,4-Difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate (4,4-difluorobut -3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.51 (s, 1H), 5.40 (q, J = 7.1 Hz, 1H), 4.33 (dtd, J = 26.5, 7.8, 2.6 Hz, 1H), 4.13-4.01 (m, 2H), 2.29-2.26 (m, 3H), 2.24-2.12 (m, 2H), 1.65 (d, J = 7.1 Hz, 3H); LCMS (M+1): 312.95 41 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propionic acid Ester (3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ6.45 (s, 1H), 4.30 (dd, J = 13.9, 8.3 Hz, 1H), 4.08-4.20 (m, 3H), 3.01-3.10 (m, 1H) ), 2.56-2.67 (m, 2H), 2.29-2.32 (m, 3H), 1.09 (d, J = 7.1 Hz, 3H); LCMS (M+1): 344.95 42 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate ( 4,4-difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.47 (s, 1H), 4.42 (dtd, J = 26.7, 7.8, 2.4 Hz, 1H), 4.32 (dd, J = 13.9, 8.3 Hz, 1H), 4.17 (dd, J = 13.9, 5.9 Hz, 1H), 3.97-4.03 (m, 2H), 3.02-3.11 (m, 1H), 2.32 (d, J = 0.7 Hz, 3H), 2.15-2.23 (m, 2H) ), 1.11 (d, J = 7.1 Hz, 3H) LCMS (M+1): 326.95 43 3,4,4-Trifluorobut-3-en-1-yl 2-(2H-indazol-2-yl)acetate (3,4,4-trifluorobut-3-en-1-yl 2-( 2H-indazol-2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.37 (d, J = 1.0 Hz, 1H), 7.68 - 7.74 (m, 1H), 7.54 - 7.60 (m, 1H), 7.24 (ddd, J = 8.8, 6.6, 1.2 Hz, 1H), 7.04 (ddd, J = 8.4, 6.6, 0.9 Hz, 1H), 5.43 (s, 2H), 4.28 (t, J = 6.0 Hz, 2H), 2.63-2.73 (m, 2H) ); LCMS (M+1): 285.30 44 4,4-Difluorobut-3-en-1-yl 2-(2H-indazol-2-yl) acetate (4,4-difluorobut-3-en-1-yl 2-(2H-indazol- 2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.38 (d, J = 0.7 Hz, 1H), 7.72 (dt, J = 8.4, 1.1 Hz, 1H), 7.58 (dq, J = 8.8, 1.0 Hz, 1H) ), 7.24 (ddd, J = 8.7, 6.5, 1.2 Hz, 1H), 7.04 (ddd, J = 8.5, 6.5, 0.9 Hz, 1H), 5.40 (d, J = 10.5 Hz, 2H), 4.49 (dtd, J = 26.7, 7.8, 2.6 Hz, 1H), 4.14 (td, J = 6.4, 0.7 Hz, 2H), 2.30-2.24 (m, 2H); LCMS (M+1): 267 45 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate (3,4, 4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.03 (s, 2H), 4.26 (t, J = 6.0 Hz, 2H), 2.63-2.73 (m, 2H), 2.26 (s, 3H), 2.14 (s , 3H); LCMS (M+1): 263.95 46 2-(4-Chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl)acetamide (2-(4-chloro-1H -pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl)acetamide) ¹H-NMR (400 MHz, DMSO-D6) δ 8.12-8.51 (m, 1H), 7.83-7.99 (s, 1H), 7.43-7.60 (s, 1H), 4.93-4.68 (m, 2H), 3.22- 3.33 (m, 2H), 2.40-2.55 (m, 2H); LCMS (M+1): 267.80 47 3,4,4-Trifluorobut-3-en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl)acetate (3,4,4-trifluorobut-3 -en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 5.59 (s, 2H), 4.43 (t, J = 6.2 Hz, 2H), 2.63-2.73 (m, 2H); LCMS (M-1): 302.7 48 3,4,4-Trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (3,4,4-trifluorobut-3-en- 1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.43 (s, 1H), 4.69 (s, 2H), 4.38 (t, J = 6.1 Hz, 2H), 2.61-2.71 (m, 2H); LCMS (M +1): 302.85 49 4,4-Difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate (4,4-difluorobut- 3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.02 (s, 2H), 4.49 (dtd, J = 26.7, 7.8, 2.6 Hz, 1H), 4.12 (td, J = 6.2, 0.7 Hz, 2H), 2.30 -2.24 (m, 5H), 2.14 (s, 3H); LCMS (M+1): 246.05 50 4,4-Difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3-en-1 -yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.79 (s, 1H), 5.09 (q, J = 7.0 Hz, 1H), 4.35 (dtd, J = 26.7, 7.8, 2.6 Hz, 1H), 4.09-4.01 (m, 2H), 2.21-2.17 (m, 2H), 2.16 (dd, J = 3.2, 2.6 Hz, 3H), 2.07-2.05 (m, 3H), 1.57 (d, J = 7.0 Hz, 3H); LCMS (M+1): 259.00 51 4,4-Difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropionate (4,4-difluorobut- 3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.74 (s, 1H), 4.44 (dtd, J = 26.7, 7.8, 2.6 Hz, 1H), 4.11 (dd, J = 13.8, 7.6 Hz, 1H), 4.00 (dd, J = 6.7, 5.8 Hz, 2H), 3.92 (q, J = 6.8 Hz, 1H), 2.97 (td, J = 14.2, 7.2 Hz, 1H), 2.25-2.17 (m, 2H), 2.15 ( d, J = 9.5 Hz, 3H), 2.06-2.04 (m, 3H), 1.08-1.00 (m, 3H); LCMS (M+1): 273.15 52 2-(4-Chloro-1H-pyrazol-1-yl)-N-(4,4-difluorobut-3-en-1-yl)acetamide (2-(4-chloro-1H-pyrazol) -1-yl)-N-(4,4-difluorobut-3-en-1-yl)acetamide) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.53 (d, J = 15.4 Hz, 1H), 7.47-7.45 (m, 1H), 6.25 (s, 1H), 4.74 (s, 2H), 4.07 (dtd , J = 25.0, 8.0, 2.2 Hz, 1H), 3.28 (q, J = 6.5 Hz, 2H), 2.18-2.12 (m, 2H); LCMS (M+1): 249.85 53 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetamide (3,4,4-trifluorobut-3-en-1 -yl 2-(1H-benzo[d]imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.17 (s, 1H), 7.64-7.66 (m, 1H), 7.48-7.51 (m, 1H), 7.18-7.26 (m, 2H), 5.28 (s, 2H), 4.28 (t, J = 6.0 Hz, 2H), 2.63-2.74 (m, 2H); LCMS (M+1): 284.9 54 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-imidazol-1-yl) acetate (3,4,4-trifluorobut-3-en-1-yl 2-(1H -imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.59 (s, 1H), 7.11 (s, 1H), 6.88 (s, 1H), 4.97 (d, J = 7.8 Hz, 2H), 4.26 (t, J = 6.0 Hz, 2H), 2.64-2.75 (m, 2H); LCMS (M+1): 234.9 55 4,4-Difluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate (4,4-difluorobut-3-en-1-yl 2-( 1H-benzo[d]imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.18 (s, 1H), 7.65 (dt, J = 7.4, 0.9 Hz, 1H), 7.51 (dt, J = 7.5, 1.0 Hz, 1H), 7.26-7.18 (m, 2H), 5.26 (s, 2H), 4.48 (dtd, J = 26.7, 7.8, 2.5 Hz, 1H), 4.13 (dd, J = 6.4, 5.6 Hz, 2H), 2.32-2.24 (m, 2H) ); LCMS (M+1): 267 56 4,4-Difluorobut-3-en-1-yl 2-(1H-imidazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2-(1H-imidazol-1 -yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.59 (s, 1H), 7.12 (s, 1H), 6.88 (s, 1H), 4.96 (s, 2H), 4.51 (dtd, J = 26.7, 7.8, 2.5 Hz, 1H), 4.11 (td, J = 6.4, 0.7 Hz, 2H), 2.31-2.25 (m, 2H); LCMS (M+1): 216.95 57 3,4,4-Trifluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (3,4,4-trifluorobut-3 -en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.38-8.37 (m, 1H), 7.92 (s, 1H), 5.17 (d, J = 4.6 Hz, 2H), 4.26 (t, J = 6.0 Hz, 2H) ), 2.72-2.62 (m, 2H); LCMS (M+1): 302.85 58 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropionate ( 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.21-4.09 (m, 3H), 3.99 (dd, J = 13.9, 6.1 Hz, 1H), 2.99 (td, J = 14.2, 7.1 Hz, 1H), 2.68 -2.57 (m, 2H), 2.17 (s, 3H), 2.05 (s, 3H), 1.04 (d, J = 7.3 Hz, 3H); LCMS (M+1): 325.05 59 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)propionate (3,4,4 -trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.28-5.20 (m, 1H), 4.31-4.04 (m, 2H), 2.68-2.55 (m, 2H), 2.17 (d, J = 4.9 Hz, 3H) , 2.08 (d, J = 7.6 Hz, 3H), 1.66-1.58 (m, 3H); LCMS (M+1): 311.00 60 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropionate (4, 4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.42 (dtd, J = 26.7, 7.8, 2.6 Hz, 1H), 4.17 (dd, J = 13.9, 8.1 Hz, 1H), 4.02-3.97 (m, 3H) , 3.03-2.94 (m, 1H), 2.25-2.11 (m, 5H), 2.05-1.98 (m, 3H), 1.05 (d, J = 7.1 Hz, 3H); LCMS (M+1): 307.05 61 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3 -en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.25-5.19 (m, 1H), 4.35 (dtd, J = 26.5, 7.9, 2.6 Hz, 1H), 4.10-4.01 (m, 2H), 2.28-2.16 ( m, 5H), 2.09 (d, J = 10.3 Hz, 3H), 1.64-1.58 (m, 3H); LCMS (M+1): 292.9 62 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3 -en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.78 (s, 1H), 5.10 (q, J = 7.0 Hz, 1H), 4.18 (t, J = 5.9 Hz, 2H), 2.65-2.55 (m, 2H) ), 2.15 (d, J = 0.5 Hz, 3H), 2.05 (s, 3H), 1.57 (d, J = 7.1 Hz, 3H); LCMS (M+1): 277.00 63 4,4-Difluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl) acetate (4,4-difluorobut-3-en-1-yl 2-( 2-methyl-1H-imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.99 (d, J = 1.2 Hz, 1H), 6.70 (d, J = 1.2 Hz, 1H), 4.88 (s, 2H), 4.50 (dtd, J = 26.7 , 7.8, 2.4 Hz, 1H), 4.14-4.11 (m, 2H), 2.31-2.25 (m, 2H), 2.18 (s, 3H); LCMS (M+1): 230.9 64 4,4-Difluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl) acetate (4,4-difluorobut-3-en-1-yl 2- (5-methyl-2H-tetrazol-2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.76 (s, 2H), 4.51 (dtd, J = 26.7, 7.8, 2.7 Hz, 1H), 4.17 (td, J = 6.3, 0.7 Hz, 2H), 2.49 (s, 3H), 2.32-2.26 (m, 2H); LCMS (M+1): 232.9 65 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)acetate (3,4,4-trifluorobut-3-en-1 -yl 2-(5-methyl-2H-tetrazol-2-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.76 (s, 2H), 4.29 (t, J = 6.0 Hz, 2H), 2.73-2.68 (m, 1H), 2.67-2.62 (m, 1H), 2.46 (s, 3H); LCMS (M+1): 250.8 66 4,4-Difluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (4,4-difluorobut-3-en-1 -yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.38 (t, J = 0.9 Hz, 1H), 7.92 (s, 1H), 5.16 (s, 2H), 4.48 (dtd, J = 26.7, 7.8, 2.4 Hz , 1H), 4.12 (td, J = 6.3, 0.6 Hz, 2H), 2.29-2.23 (m, 2H); LCMS (M-1): 282.80 67 4,4-Difluorobut-3-en-1-yl 2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate (4,4-difluorobut-3-en- 1-yl 2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.49-7.45 (m, 1H), 7.44-7.40 (m, 1H), 7.16-7.09 (m, 2H), 5.30 (s, 2H), 4.47 (dtd, J = 26.7, 7.8, 2.5 Hz, 1H), 4.14 (t, J = 6.1 Hz, 2H), 2.27 (ddt, J = 14.2, 6.4, 1.7 Hz, 2H), 2.16-2.10 (m, 1H), 1.03 -0.95 (m, 4H); LCMS (M+1): 306.6 68 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetate (3,4,4- trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.06 (dt, J = 8.4, 0.9 Hz, 1H), 7.82 (dt, J = 8.4, 0.9 Hz, 1H), 7.58-7.54 (m, 1H), 7.42 (ddd, J = 8.4, 6.9, 1.0 Hz, 1H), 5.81 (s, 2H), 4.28 (t, J = 5.9 Hz, 2H), 2.71-2.61 (m, 2H); LCMS (M+1): 286.3 69 4,4-Difluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetate (4,4-difluorobut-3- en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.06 (dt, J = 8.4, 0.9 Hz, 1H), 7.83 (dt, J = 8.3, 1.0 Hz, 1H), 7.58-7.54 (m, 1H), 7.42 (ddd, J = 8.3, 6.8, 1.0 Hz, 1H), 5.79 (s, 2H), 4.45 (dtd, J = 26.7, 7.8, 2.4 Hz, 1H), 4.16-4.13 (m, 2H), 2.29-2.23 (m, 2H); LCMS (M+1): 268.3 70 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-1H-tetrazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1 -yl 2-(5-methyl-1H-tetrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.51 (d, J = 7.1 Hz, 2H), 4.31 (t, J = 6.0 Hz, 2H), 2.75-2.65 (m, 2H), 2.47 (t, J = 3.5 Hz, 3H); LCMS (M+1): 251.3 71 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate (3,4,4 -trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.62 (s, 1H), 5.57 (q, J = 7.0 Hz, 1H), 4.27-4.17 (m, 2H), 2.63-2.54 (m, 2H), 1.74 (d, J = 7.1 Hz, 3H); LCMS (M-1): 382.75 72 4,4-Difluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate (4,4-difluorobut-3 -en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.62 (s, 1H), 5.55 (q, J = 7.0 Hz, 1H), 4.31 (dtd, J = 26.4, 7.9, 2.6 Hz, 1H), 4.15-4.04 (m, 2H), 2.20-2.14 (m, 2H), 1.74 (d, J = 6.8 Hz, 3H); LCMS (M-1): 365.00 73 3,4,4-Trifluorobut-3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1- yl 2-(3-chloro-1H-indazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.69 (tt, J = 8.1, 1.0 Hz, 2H), 7.53-7.49 (m, 1H), 7.29-7.25 (m, 1H), 5.42 (s, 2H) , 4.24 (t, J = 5.9 Hz, 2H), 2.68-2.58 (m, 2H); LCMS (M+1): 318.85 74 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropionate (3,4, 4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.74 (s, 1H), 4.20-4.08 (m, 3H), 3.96-3.89 (m, 1H), 2.97 (q, J = 7.1 Hz, 1H), 2.69 -2.58 (m, 2H), 2.16 (d, J = 0.5 Hz, 3H), 2.06-2.03 (m, 3H), 1.03-1.00 (m, 3H); LCMS (M+1): 291.30 75 3,4,4-Trifluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl)acetate (3,4,4-trifluorobut-3-en-1- yl 2-(2-methyl-1H-imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.99 (d, J = 1.5 Hz, 1H), 6.70 (d, J = 1.2 Hz, 1H), 4.89 (d, J = 7.6 Hz, 2H), 4.27 ( t, J = 6.0 Hz, 2H), 2.75-2.64 (m, 2H), 2.18 (d, J = 4.2 Hz, 3H); LCMS (M+1): 248.6 76 3,4,4-Trifluorobut-3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl)acetate (3,4,4-trifluorobut -3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.92 (d, J = 14.2 Hz, 2H), 4.30 (t, J = 6.0 Hz, 2H), 2.75-2.65 (m, 2H), 2.25 (s, 3H) ); LCMS (M+1): 316.5 77 3,4,4-Trifluorobut-3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropanoate (3,4,4-trifluorobut- 3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.70-7.68 (m, 1H), 7.49-7.41 (m, 2H), 7.29-7.25 (m, 1H), 4.24 (t, J = 6.0 Hz, 2H) , 2.62-2.52 (m, 2H), 1.88 (s, 6H); LCMS (M+1): 346.55 78 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3-en-1-yl 2- (1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.78 (dd, J = 2.4, 0.5 Hz, 1H), 7.44 (t, J = 0.9 Hz, 1H), 6.25 (dd, J = 2.3, 1.8 Hz, 1H) ), 5.27 (q, J = 7.3 Hz, 1H), 4.21 (t, J = 5.9 Hz, 2H), 2.67-2.57 (m, 2H), 1.64 (d, J = 7.3 Hz, 3H); LCMS (M +1): 248.55 79 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3-en- 1-yl 2-methyl-2-(1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.86 (dd, J = 2.4, 0.7 Hz, 1H), 7.44 (q, J = 0.7 Hz, 1H), 6.26 (dd, J = 2.4, 1.7 Hz, 1H) ), 4.18 (t, J = 5.7 Hz, 2H), 2.64-2.54 (m, 2H), 1.74 (s, 6H); LCMS (M+1): 262.10 80 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut- 3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.06 (q, J = 1.1 Hz, 1H), 6.74 (dd, J = 2.4, 0.5 Hz, 1H), 5.46 (q, J = 7.3 Hz, 1H), 4.23 (t, J = 5.9 Hz, 2H), 2.67-2.57 (m, 2H), 1.68 (d, J = 7.3 Hz, 3H); LCMS (M+1): 316.55 81 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate (3,4 ,4-trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.17 (q, J = 1.1 Hz, 1H), 6.75 (d, J = 2.2 Hz, 1H), 4.20 (t, J = 5.7 Hz, 2H), 2.65- 2.55 (m, 2H), 1.79 (s, 6H); LCMS (M+1): 330.50 82 3,4,4-Trifluorobut-3-en-1-yl 2-(4-phenyl-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3-en- 1-yl 2-(4-phenyl-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.15 (d, J = 0.7 Hz, 1H), 7.92 (d, J = 0.7 Hz, 1H), 7.57-7.54 (m, 2H), 7.37-7.33 (m , 2H), 7.21-7.17 (m, 1H), 5.10-5.07 (m, 2H), 4.29-4.23 (m, 2H), 2.74-2.62 (m, 2H); LCMS (M+1): 310.60 83 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)propionate (3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.26 (s, 2H), 4.27 (t, J = 5.8 Hz, 2H), 2.73-2.62 (m, 2H), 2.24 (s, 3H); LCMS (M +1): 350.60 84 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate ( 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 5.26 (s, 2H), 4.27 (t, J = 5.9 Hz, 2H), 2.72-2.62 (m, 2H), 2.24-2.19 (m, 3H); LCMS (M+1): 350.60 85 3,4,4-Trifluorobut-3-en-1-yl 2-(4-(3,5-difluorophenyl)-1H-pyrazol-1-yl)acetate (3,4,4 -trifluorobut-3-en-1-yl 2-(4-(3,5-difluorophenyl)-1H-pyrazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.30 (d, J = 0.5 Hz, 1H), 8.05 (d, J = 0.7 Hz, 1H), 7.37-7.32 (m, 2H), 7.02 (tt, J = 9.4, 2.3 Hz, 1H), 5.11 (s, 2H), 4.27 (t, J = 6.0 Hz, 2H), 2.74-2.63 (m, 2H); LCMS (M+1): 346.50 86 3,4,4-Trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)propanoate (3,4,4 -trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)propanoate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 7.90-7.85 (m, 2H), 7.42-7.37 (m, 2H), 5.71 (q, J = 7.3 Hz, 1H), 4.33-4.27 (m, 2H) , 2.61-2.51 (m, 2H), 2.06 (d, J = 7.3 Hz, 3H); LCMS (M+1): 299.9 87 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)propionate (3,4,4-trifluorobut-3-en- 1-yl 2-(5-methyl-2H-tetrazol-2-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.02 (q, J = 7.3 Hz, 1H), 4.31-4.21 (m, 2H), 2.68-2.58 (m, 2H), 2.45 (s, 3H), 1.78 (d, J = 7.1 Hz, 3H) 88 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)propanoate (3,4,4 -trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)propanoate) ¹H-NMR (400 MHz, CHLOROFORM-D) δ 8.09-8.07 (m, 1H), 7.52-7.47 (m, 2H), 7.41-7.36 (m, 1H), 5.70 (q, J = 7.4 Hz, 1H) , 4.30 (ddd, J = 23.2, 11.0, 6.2 Hz, 2H), 2.59-2.48 (m, 2H), 2.05-2.00 (m, 3H); LCMS (M+1): 299.95 89 3,4,4-Trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)acetate (3,4,4 -trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.85-7.83 (m, 1H), 7.80 (dd, J = 8.2, 0.9 Hz, 1H), 7.50-7.46 (m, 1H), 7.42-7.38 (m, 1H), 5.44 (d, J = 0.7 Hz, 2H), 4.29 (t, J = 5.7 Hz, 2H), 2.70-2.60 (m, 2H); LCMS (M+1): 353.3 90 3,4,4-Trifluorobut-3-en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1-yl)acetate (3,4,4-trifluorobut-3 -en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1-yl)acetate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.53-7.49 (m, 1H), 7.44-7.40 (m, 1H), 7.18-7.11 (m, 2H), 5.21 (s, 2H), 4.29 (t, J = 6.0 Hz, 2H), 2.74-2.64 (m, 2H), 2.44 (s, 3H); LCMS (M+1): 299.30 91 3,4,4-Trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropionate ( 3,4,4-trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.95-7.90 (m, 2H), 7.47-7.42 (m, 2H), 4.24 (t, J = 5.6 Hz, 2H), 2.62-2.52 (m, 2H) , 2.01 (s, 6H); LCMS (M+1): 314.0 92 3,4,4-Trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropionate ( 3,4,4-trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.08 (dt, J = 8.3, 1.0 Hz, 1H), 7.65 (dt, J = 8.4, 0.9 Hz, 1H), 7.54-7.50 (m, 1H), 7.43 -7.39 (m, 1H), 4.26 (t, J = 5.7 Hz, 2H), 2.64-2.53 (m, 2H), 2.00 (d, J = 21.8 Hz, 6H); LCMS (M+1): 314.0 93 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propionate (3,4,4-trifluorobut -3-en-1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.25 (t, J = 5.7 Hz, 2H), 2.67-2.57 (m, 2H), 2.46-2.43 (m, 3H), 1.92 (s, 6H); LCMS (M+1): 278.85 94 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)butyrate (3,4,4-trifluorobut-3-en-1 -yl 2-(4-chloro-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.09-8.07 (m, 1H), 7.57 (d, J = 0.6 Hz, 1H), 5.07-5.00 (m, 1H), 4.28-4.21 (m, 2H) , 2.68-2.58 (m, 2H), 2.13-2.05 (m, 2H), 0.81-0.74 (m, 3H); LCMS (M+1): 296.85 95 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)butyrate (3,4,4 -trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.99 (dt, J = 15.5, 7.1 Hz, 1H), 4.23-4.14 (m, 2H), 2.64-2.54 (m, 2H), 2.23-2.17 (m, 2H), 2.12-2.06 (m, 6H), 0.74 (t, J = 7.3 Hz, 3H); LCMS (M+1): 324.90 96 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate (3,4,4-trifluorobut- 3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.06 (q, J = 1.1 Hz, 1H), 6.75 (d, J = 2.4 Hz, 1H), 5.26-5.21 (m, 1H), 4.26-4.21 (m , 2H), 2.67-2.57 (m, 2H), 2.20-2.08 (m, 2H), 0.80-0.74 (m, 3H); LCMS (M+1): 330.85 97 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate (3,4 ,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.51 (s, 1H), 5.20 (dd, J = 9.2, 6.0 Hz, 1H), 4.26-4.16 (m, 2H), 2.65-2.55 (m, 2H) , 2.32-2.28 (m, 3H), 2.20-2.06 (m, 2H), 0.78-0.70 (m, 3H); LCMS (M+1): 344.60 98 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butyrate (3,4,4 -trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.64 (s, 1H), 5.34 (dd, J = 9.3, 5.4 Hz, 1H), 4.27-4.16 (m, 2H), 2.66-2.52 (m, 2H) , 2.31-2.16 (m, 2H), 0.85-0.69 (m, 3H); LCMS (M-1): 396.35 99 3,4,4-Trifluorobut-3-en-1-yl 2-(3-methyl-1H-pyrazol-1-yl)butyrate (3,4,4-trifluorobut-3-en- 1-yl 2-(3-methyl-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.63 (d, J = 2.2 Hz, 1H), 6.04-6.01 (m, 1H), 4.92-4.88 (m, 1H), 4.22-4.16 (m, 2H) , 2.68-2.55 (m, 2H), 2.16-2.11 (m, 3H), 2.10-2.01 (m, 2H), 0.77-0.71 (m, 3H); LCMS (M+1): 276.90 100 3,4,4-Trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)butyrate (3,4,4-trifluorobut-3-en- 1-yl 2-(3-methyl-1H-indazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.69 (dt, J = 8.1, 1.0 Hz, 1H), 7.58 (t, J = 8.3 Hz, 1H), 7.37-7.33 (m, 1H), 7.13-7.09 (m, 1H), 5.42 (dd, J = 9.3, 6.1 Hz, 1H), 4.21-4.12 (m, 2H), 2.59-2.51 (m, 2H), 2.47 (d, J = 4.6 Hz, 3H), 2.30-2.18 (m, 2H), 0.79-0.68 (m, 3H); LCMS (M+1): 328.10 101 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-3-methylbutyrate (3,4,4-trifluorobut- 3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-3-methylbutanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.06 (d, J = 0.5 Hz, 1H), 7.57 (d, J = 0.5 Hz, 1H), 4.78 (d, J = 9.3 Hz, 1H), 4.30- 4.21 (m, 2H), 2.71-2.60 (m, 2H), 2.56-2.42 (m, 1H), 0.93 (d, J = 6.6 Hz, 3H), 0.74 (d, J = 6.8 Hz, 3H); LCMS (M+1): 310.65 102 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutyrate ( 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.65 (s, 1H), 4.96 (d, J = 8.6 Hz, 1H), 4.31-4.19 (m, 2H), 2.70 (dt, J = 21.8, 6.7 Hz , 1H), 2.64-2.53 (m, 2H), 1.04 (d, J = 6.8 Hz, 3H), 0.80 (d, J = 6.6 Hz, 3H); LCMS (M-1): 411.3 103 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)butanoic acid Ester (3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 6.51 (s, 1H), 4.89 (d, J = 9.0 Hz, 1H), 4.29-4.15 (m, 2H), 2.65-2.56 (m, 2H), 2.50 -2.43 (m, 1H), 2.30 (s, 3H), 1.01 (d, J = 6.8 Hz, 3H), 0.73 (d, J = 6.6 Hz, 3H); LCMS (M+1): 359.15 104 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazol-1-yl)butyrate (3, 4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.71 (dt, J = 8.3, 1.6 Hz, 2H), 7.39-7.34 (m, 2H), 7.28-7.24 (m, 1H), 6.48 (d, J = 0.7 Hz, 1H), 4.73-4.69 (m, 1H), 4.23 (t, J = 5.9 Hz, 2H), 2.73-2.56 (m, 3H), 2.28 (d, J = 0.4 Hz, 3H), 1.04 ( dd, J = 6.7, 2.8 Hz, 3H), 0.78 (d, J = 6.6 Hz, 3H); LCMS (M+1): 366.95 105 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-3-methylbutyrate ( 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-3-methylbutanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 4.65 (d, J = 9.5 Hz, 1H), 4.28-4.14 (m, 2H), 2.72-2.52 (m, 3H), 2.24-2.19 (m, 3H) , 2.09-2.03 (m, 3H), 1.08-0.98 (m, 3H), 0.74-0.69 (m, 3H); LCMS (M+1): 339.30 106 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-3-methylbutyrate (3,4, 4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-3-methylbutanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.83-7.81 (m, 2H), 7.57-7.50 (m, 3H), 7.48-7.46 (m, 2H), 7.43-7.39 (m, 2H), 7.33- 7.29 (m, 1H), 6.86 (s, 1H), 4.55 (d, J = 9.3 Hz, 1H), 4.28 (t, J = 5.7 Hz, 2H), 2.71-2.62 (m, 3H), 0.95-0.88 (m, 3H), 0.64 (d, J = 6.6 Hz, 3H); LCMS (M+1): 334.95 107 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-1H-pyrazol-1-yl)butyrate (3,4,4-trifluorobutyrate) -3-en-1-yl 3-methyl-2-(3-methyl-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.63 (d, J = 2.2 Hz, 1H), 6.04 (d, J = 2.2 Hz, 1H), 4.63 (dd, J = 9.4, 2.1 Hz, 1H), 4.27-4.16 (m, 2H), 2.72-2.59 (m, 2H), 2.47-2.39 (m, 1H), 2.10 (d, J = 17.6 Hz, 3H), 0.92 (d, J = 6.6 Hz, 3H) , 0.77-0.70 (m, 3H); LCMS (M+1): 290.9 108 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate (3,4 ,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 8.06 (q, J = 1.1 Hz, 1H), 6.76 (d, J = 2.4 Hz, 1H), 5.02 (d, J = 9.0 Hz, 1H), 4.27 ( t, J = 5.9 Hz, 2H), 2.70-2.60 (m, 2H), 2.56-2.52 (m, 1H), 0.95 (d, J = 6.8 Hz, 3H), 0.75 (d, J = 6.8 Hz, 3H) ); LCMS (M+1): 344.50 109 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1-yl)butyrate (3,4,4-trifluorobutyrate) -3-en-1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1-yl)butanoate) ¹H-NMR (400 MHz, DMSO-D6) δ 7.53 (t, J = 0.7 Hz, 1H), 7.24 (s, 1H), 4.65 (d, J = 9.5 Hz, 1H), 4.24 (qd, J = 11.5 , 5.5 Hz, 2H), 2.70-2.60 (m, 2H), 2.46-2.39 (m, 1H), 1.99 (d, J = 6.4 Hz, 3H), 0.92 (d, J = 6.8 Hz, 3H), 0.71 (d, J = 6.8 Hz, 3H); LCMS (M+1): 290.90 *The English names of the compounds were generated using Chemdraw Professional 19.1 software

As described herein, compounds of formula (I) exhibit high nematicidal activity against nematodes that attack important crops. The following lines evaluate the activity of compounds of the invention against one or more of the following nematodes.

biological example

Examples of biological tests for plant-parasitic nematodes

Example 1: Meloidogyne incognita (Root-knot nematode): in vitro testing

Meloidogyne incognita: Test compounds at a concentration of 300 ppm were pipetted into wells of a 24-well microtiter plate, each well containing 500 μL of distilled water and 50 M. incognita larvae. The suspension was shaken slightly to mix the compounds evenly. The coupons were covered with lids and incubated at 25 °C and 90% RH. Dead/inactivated nematodes were counted under the microscope at 48, 72 and 96 hour intervals, and percent mortality was calculated by comparing the results of the treatments to those of the untreated controls. Compounds 8, 17, 25, 35, 36, 37, 44, 47, 55, 56, 57, 58, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 74 and 75 at 300 The ppm test showed more than 70% mortality, while there was no mortality in the untreated inspection.

Southern root knot nematode: in vivo testing

Gherkin plants were grown in a 1:1:1:1 ratio in nursery trays containing a mixture of sand:soil:manure (FYM):coconut oil. When the cucumber seedlings are ten days old, apply 1 mL of the test compound of the desired test concentration to the soil with the help of a micropipette. After application, seedlings were inoculated with approximately 2000 newly hatched second stage seedlings of R. incognita. Treated plants were allowed to grow under greenhouse conditions at a temperature of 27 °C. Observations of gall grades were recorded 15 days after application. Plants were carefully uprooted and roots washed thoroughly. Gall scales are observed on a scale of 0-10, as described by Zeck (1971), as follows:

0 = no galls

1 = very few small galls

2 = Lots of small galls

3 = Many small galls, some of which grow together

4 = Lots of small galls and some large galls

5 = 25% of roots severely gall

6 = 50% of roots severely gall

7 = 75% of roots severely gall

8 = Unhealthy roots but still green plant

9 = Root rot and plant withered

10 = Plant and roots die

Compounds 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 16, 17, 18, 20, 24, 25, 26, 35, 36, 38, 44, 47, 48, 54, 55 , 56, 61, 63, 64, 66, 67, 68, 69, 70, and 75 recorded gall ratings below 3 in the 300 ppm test, with a high number of galls (up to 8) present in the untreated inspection.

化合物編號21 3.6 PCT專利公開號WO2019186498

化合物編號13 2 本發明的化合物

化合物編號12 0.8 本發明的化合物

化合物編號75 1.2 In addition, Table A presents the results of the efficacy of the compounds of the present invention compared to compounds known in the prior art. compound Gal Index at 200 ppm compound concentration PCT Patent Publication No. WO2020157668

Compound No. 21 3.6 PCT Patent Publication No. WO2019186498

Compound No. 13 2 Compounds of the present invention

Compound No. 12 0.8 Compounds of the present invention

Compound No. 75 1.2

The present invention has been described with reference to certain preferred aspects, other aspects will become apparent to those skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications can be made to the materials and methods without departing from the scope of the invention.

Claims (18)

A compound of general formula (I);

Formula (I) wherein, Y represents O or NR ⁵ ; R ¹ is selected from the group consisting of H and F; R ² and R ³ are independently selected from the group consisting of H and C ₁ -C ₃ alkyl Group; Ring A represents a ring system selected from A1 to A12, wherein ^A is optionally substituted with one or more R4;

R ⁴ is selected from X, CN, (C=O)-R ⁶ , OR ⁵ , N(R ⁵ ) ₂ , S(O) _n R ⁶ , C ₁ -C ₆ alkyl, C1-C6 haloalkyl , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl -C ₁ -C ₆ The group consisting of alkyl, phenyl and C ₃ -C ₆ heterocyclyl; each group of R ⁴ is optionally selected from halogen, R ^5a , OR ^5a , SR ^5a , N(R ^5a ) ₂ , One or more groups of the group consisting of Si(R ^5a ) ₃ , COOR ^5a , CN and CON(R ^5a ) ₂ are substituted; R ⁵ is selected from H, C ₁ -C ₄ alkyl, C ₃ - The group consisting of C ₆ cycloalkyl and C ₃ -C ₆ cycloalkyl-C ₁ -C ₃ alkyl; R ^5a is selected from H, C ₁ -C ₆ alkyl and C ₃ -C ₆ cycloalkane The group consisting of radicals; R ⁶ is selected from N(R ^5a ) ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkane group consisting of C _{2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl and} C ₃ -C ₆ cycloalkyl; R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ^5a and R ⁶ are optionally selected from X, CN, C ₁ -C ₄ alkyl, OC ₁ -C ₄ alkyl, S(O) _n -C ₁ -C ₄ alkyl and C ₃ -C ₆ One or more substitutions of the group consisting of cycloalkyl; X represents halogen; n represents an integer, wherein n=0, 1 and 2; and/or its stereoisomer or its agriculturally acceptable salt or its tautomer or its N-oxide. A compound of formula (I) as claimed in claim 1, wherein: Y represents O; Ring A represents a ring system selected from A1 to A7, wherein ^A is optionally substituted by one or more R4;

R ⁴ is selected from X, CN, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₁₂ cycloalkyl , C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl group, phenyl and C ₃ -C ₆ heterocyclic group; each group of R ⁴ The group is optionally selected from the group consisting of halogen, R ^5a , OR ^5a , SR ^5a , N(R ^5a ) ₂ , Si(R ^5a ) ₃ , COOR ^5a , CN and CON(R ^5a ) ₂ and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof. A compound of formula (I) as claimed in claim 1, wherein: Y represents O; Ring A represents a ring system selected from A8 to A12, wherein ^A is optionally substituted by one or more R4;

R ⁴ is selected from X, CN, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₁₂ cycloalkyl , C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl group, phenyl and C ₃ -C ₆ heterocyclic group; each group of R ⁴ The group is optionally selected from the group consisting of halogen, R ^5a , OR ^5a , SR ^5a , N(R ^5a ) ₂ , Si(R ^5a ) ₃ , COOR ^5a , CN and CON(R ^5a ) ₂ and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof. A compound of formula (I) as claimed in claim 1, wherein: Ring A represents a ring system selected from A1, A2, A6 and A7, wherein ^A is optionally substituted by one or more R4;

and/or its stereoisomers or their agriculturally acceptable salts or their tautomers or their N-oxides. A compound of formula (I) as claimed in claim 1, wherein: Y represents O; Ring A represents a ring system selected from A1 to A12, wherein ^A is optionally substituted with one or more R4 ^; and R4 is is selected from the group consisting of X, CN, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, R ^5a C=NOR ^5a and -C ₁ -C ₆ -alkyl-OR ⁵ . The compound of claim 1, wherein the compound of formula (I) is selected from the group consisting of: (4,4-difluorobut-3-en-1-yl 2-(5-methyl- 3-(Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl) -1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate ; 4,4-Difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate; 4,4-Difluorobut-3-en-1- 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5- Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(5-cyclopropyl-3- (Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl) Acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate; 3,4,4-Trifluorobut-3-ene- 1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl) -1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazole- 1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-indazol-1-yl) acetate; 3,4,4-trifluorobut-3-ene -1-yl 2-(1H-indazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1- yl) propionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobutane -3-En-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropionate; 4,4-difluorobut-3-en-1-yl 2- (4-Chloro-1H-pyrazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5 -Dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyridine azol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propionate; 4,4-Difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propionate; 3,4,4-Trifluorobutan-3 -ene -1-yl 2-(4-methyl-1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(4-methyl-1H- Pyrazol-1-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl) Propionate; 4,4-Difluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propionate; 3,4,4 -Trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-Diphenyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(difluoromethyl) )-2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-2H-indazol-2-yl)acetate ; 4,4-Difluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl) acetate; 4,4-Difluorobut-3-en-1- 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis (Difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate ; 4,4-Difluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl) acetate; 3,4,4-Trifluorobut-3-en-1-yl 2- (3-(Trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H - Pyrazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazole- 1-yl)propionate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propane acid ester; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl ) propionate; 4,4-difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl ) propionate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-indazol-2-yl) acetate; 4,4-difluorobut-3-ene-1 -yl 2-(2H-indazol-2-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2 ,4-Triazol-1-yl)acetate; 2-(4-Chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl ) acetamide; 3,4,4-trifluorobut-3-en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl)acetate; 3,4, 4-Trifluorobut-3-ene-1 -yl 2-(4,5-dichloro-1H-imidazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H -1,2,4-Triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazole-1- base) propionate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropionate; 2-(4-Chloro-1H-pyrazol-1-yl)-N-(4,4-difluorobut-3-en-1-yl)acetamide; 3,4,4-trifluorobutane- 3-En-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-imidazol- 1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 4,4-difluorobutan-3 -En-1-yl 2-(1H-imidazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H - Pyrazol-1-yl)acetate; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1- yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazole-1- yl) propionate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methyl Propionate; 4,4-Difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)propionate; 3,4 ,4-Trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propionate; 4,4-difluorobut-3-ene- 1-yl 2-(2-methyl-1H-imidazol-1-yl) acetate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazole- 2-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl) acetate; 4,4-difluoro But-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2- (2-Cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-benzo[d] [1,2,3]Triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]tris oxazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-1H-tetrazol-1-yl)acetate; 3,4, 4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 4,4-difluorobutan-3 -ene-1 -yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-( 3-Chloro-1H-indazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazole-1 -yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl) acetate; 3, 4,4-Trifluorobut-3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl)acetate; 3,4,4-trifluorobutane -3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(1H-pyrazol-1-yl) Propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4, 4-Trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propionate; 3,4,4-tris Fluorobut-3-en-1-yl 2-(4-phenyl-1H-pyrazol-1-yl) acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 4-Chloro-3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 4-Chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-( 4-(3,5-Difluorophenyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-benzo[ d][1,2,3]Triazol-2-yl)propionate; 3,4,4-Trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazole- 2-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)propane acid ester; 3,4,4-trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)acetate; 3, 4,4-Trifluorobut-3-en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobutan-3 -En-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropanoate; 3,4,4-trifluorobutan-3 -En-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropionate; 3,4,4-trifluorobutan-3 -En-1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propionate; 3,4,4-trifluorobut-3-en-1-yl 2 -(4-Chloro-1H-pyrazol-1-yl ) butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)butyrate; 3,4,4-Trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluoro But-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobutan-3 -En-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobut-3-ene-1- 2-(3-methyl-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indium azol-1-yl)butyrate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-3-methylbutanoic acid Ester; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutanoic acid Ester; 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl) Butyrate; 3,4,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazol-1-yl)butanoic acid Ester; 3,4,4-Trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-3-methylbutanoic acid Ester; 3,4,4-Trifluorobut-3-en-1-yl 2-(3,5-phenyl-1H-pyrazol-1-yl)-3-methylbutyrate; 3,4 ,4-Trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-1H-pyrazol-1-yl)butyrate; 3,4,4-trifluorobutane- 3-En-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butyrate and 3,4,4-trifluorobut-3-ene -1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1-yl)butyrate. A method for preparing a compound of formula (I) and/or a salt thereof as claimed in claim 1, wherein the method comprises the following steps (a) to (c): a) According to the following reaction scheme, optionally in a suitable base Alkylation of a substituted compound of formula (2) with a compound of formula (3) in the presence of a solvent to give a compound of formula (4), followed by compounding of a compound of formula (4) in the presence of a suitable acid/base and solvent Hydrolysis to give compounds of formula (5):

Wherein, Ring A represents Ring A; b) according to the following reaction scheme, the compound of formula (5) is converted to the compound of formula (Ia) by alkylation of the compound of formula (5) with the compound of formula (6), to The compound of formula (1a) is obtained:

wherein Ring A represents ring A and Base represents a base; c) According to the following reaction scheme, the substituted compound of formula (5) can optionally be reacted with an amine compound of formula (6) to obtain a compound of formula (1b), followed by Compounds of formula (1b) are alkylated with compounds of formula RX to give compounds of formula (1c):

Among them, Ring A represents ring A, Base represents base, and Amide Coupling represents amide coupling. A composition for controlling or preventing phytopathogenic nematodes, comprising a compound of general formula (I), a stereoisomer, an agriculturally acceptable salt, a tautomer or an N-oxide as described in claim 1 and one or more inert carriers. The composition of claim 7, wherein the composition may further comprise one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biocides Insecticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers. The composition according to claim 7 or 8, wherein the concentration of the compound of general formula (I) ranges from 1 to 90% by weight relative to the total weight of the composition, preferably 5 to 5% relative to the total weight of the composition 50% by weight. A composition comprising a compound of general formula (I) as claimed in claim 1, a stereoisomer, an agriculturally acceptable salt, a tautomer or an N-oxide and one or more active compatible substances, which Active compatible substances are selected from fungicides, insecticides, nematicides, acaricides, bioinsecticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers. A compound of general formula (I) as claimed in claim 1 or 7 or 10, its stereoisomer, agriculturally acceptable salt, tautomer or N-oxide or its composition or composition, using Use for controlling or preventing crops and/or horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes or mites. Use of a compound of general formula (I) as claimed in claim 11 for the control or prophylaxis of crop and/or horticultural crops against nematodes. The use of the compound of general formula (I) according to claim 11 or 12, wherein the crops are selected from the group consisting of cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, Any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers, other vegetables and ornamental plants. A seed comprising a compound of formula (I) and/or a stereoisomer thereof or an agriculturally acceptable salt or tautomer or N-oxide or a composition thereof as described in claim 1 or 7 or 10 or a composition wherein the amount of the compound of formula (I) or its N-oxide or its agriculturally acceptable salt ranges from 0.1 g to 10 kg per 100 kg of seed. A method for controlling or preventing phytopathogenic microorganisms in crops and/or horticultural crops from invading practical plants, wherein the compound of general formula (I) and/or its stereoisomers as claimed in claim 1 or 7 or 10 and/or a An acceptable salt or tautomer or N-oxide or composition or composition is applied to a plant, a part thereof, or the locus thereof. A method for controlling or preventing phytopathogenic microorganisms in crops and/or horticultural crops from invading practical plants, wherein the compound of general formula (I) and/or its stereoisomers as claimed in claim 1 or 7 or 10 and/or a An acceptable salt or tautomer or N-oxide or composition or composition is applied to the seed of a plant. A kind of use as claim 1 or 7 or 10 described general formula (1) compound and/or its stereoisomer or agriculturally acceptable salt or tautomer or N-oxide or composition or composition And a method for controlling or preventing phytopathogenic nematodes in crops and/or horticultural crops, comprising the steps of: applying an effective dose of a compound or composition or composition in the range of 1 g to 5 kg per hectare of agricultural and/or horticultural crops .