Piperidine amine compound containing fused ring, salt and n-oxide thereof, and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a piperidine amine compound containing a fused ring, a salt and an N-oxide thereof, and a use thereof. The compound is represented by general formula I, X1, X2, X4, X5, X6, R1, R2, R3, R4 and Q each independently representing hydrogen, halogen, nitro, cyano, alkyl, etc., and X3 representing a halogen. The compound exhibits excellent control effects against harmful organisms and / or fungi, particularly nematodes.

Description

Fused-ring piperidineamine compounds, their salts and N-oxides and their applications Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a piperidine amine compound containing a fused ring, its salt and N-oxide, and their applications. Background Technology

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests have acquired resistance, becoming difficult to control with existing pesticides or fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term persistence. In this context, despite the existence of numerous known nematicides, such as DE4308014A1 which discloses fused nitrogen-containing heterocyclic compounds and their applications as insecticides and fungicides, there is still a need to develop new pest control agents with low toxicity and low persistence. Summary of the Invention

[0003] To address the aforementioned problems in the prior art, the present invention provides a piperidine amine compound containing a fused ring, its salt, and an N-oxide, wherein the compound exhibits excellent control effects against harmful organisms and / or fungi (especially nematodes).

[0004] The technical solution adopted in this invention is as follows:

[0005] A piperidine amine compound containing a fused ring, its salt, and its N-oxide:

[0006] Where X1, X2, X4, X5, X6, R1, R2, R3, R4, and Q independently represent hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, and -N(R) groups, respectively. 21 )2、-CR 21 =N-OR 21 -(CO)N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -S(CO)R 21 -O(CO)OR 21 or-(CO)OR 21 The alkyl, alkenyl, or alkynyl group is optionally selected from halogen, nitro, cyano, cycloalkyl, heterocyclic, aryl, -N(R) 21 )2、-OR 21 -(CO)R21 -SR 21 -(SO)R 21 or -(SO2)R 21 At least one group in it is replaced;

[0007] X3 represents halogen;

[0008] R 21 Each can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, aryl, or heterocyclic groups;

[0009] The aforementioned cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO)R 10 -(SO2)R 10 or -N(R) 10 The ring is substituted by at least one group in )2, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0010] R 10 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0011] And exclude the following compounds:

[0012] In one specific embodiment, X1, X2, X4, X5, X6, R1, R2, R3, R4, and Q independently represent hydrogen, halogen, nitro, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, heterocyclic, aryl, and -N(R) 21 )2、-CR 21 =N-OR 21 -(CO)N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -S(CO)R 21 -O(CO)OR21 or-(CO)OR 21 The C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group is optionally selected from halogen, nitro, cyano, C3-C8 cycloalkyl, heterocyclic, aryl, -N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 or -(SO2)R 21 At least one group in it is replaced;

[0013] R 21 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkylthio-C1-C8 alkyl, C3-C8 cycloalkyl, aryl, or heterocyclic groups.

[0014] The aforementioned C3-C8 cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO)R 10 -(SO2)R 10 or -N(R) 10 The ring is substituted by at least one group in )2, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0015] R 10 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

[0016] In another specific embodiment, X1, X2, X4, X5, X6, R1, R2, R3, R4, and Q independently represent hydrogen, halogen, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, heterocyclic, aryl, and -N(R)21 )2、-CR 21 =N-OR 21 -(CO)N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -S(CO)R 21 -O(CO)OR 21 or-(CO)OR 21 The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally selected from halogen, nitro, cyano, C3-C6 cycloalkyl, heterocyclic, aryl, -N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 or -(SO2)R 21 At least one group in it is replaced;

[0017] R 21 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C3-C6 cycloalkyl, aryl, or heterocyclic groups.

[0018] The aforementioned C3-C6 cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO)R 10 -(SO2)R 10 or -N(R) 10 The ring is substituted by at least one group in )2, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0019] R 10Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0020] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, in the compound term "alkoxyalkyl," the alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0021] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0022] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0023] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0024] Compounds of Formula I, in their respective free or salt forms, and where appropriate, their tautomers, may exist as one of the possible isomers or as mixtures thereof, for example, as pure isomers, such as enantiomers and / or diastereomers, or as mixtures of isomers, such as mixtures of enantiomers, such as racemic mixtures, diastereomer mixtures, or racemic mixtures, depending on the number of asymmetric carbon atoms present in the molecule, their absolute and relative configurations, and / or on the configuration of the non-aromatic double bonds present in the molecule; the present invention relates to these pure isomers and also to all possible mixtures of isomers and should be understood in this sense in each of the above and below, even if stereochemical details are not specifically mentioned in each case. The present invention therefore covers all such isomers and tautomers and mixtures thereof in all proportions, together with isotopic forms, such as deuterated compounds.

[0025] The present invention also covers salts or N-oxides of each compound having chemical formula I.

[0026] Those skilled in the art also understand that salts also have biological benefits in their non-salt forms because the salts of compounds are in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions.

[0027] Therefore, various salts of the compounds of the present invention (and active ingredients used in combination with the active ingredients of the present invention) can be used to control invertebrate pests and animal parasites. Salts permissible in agriculture and / or physiology include acid addition salts formed with the following inorganic or organic acids, such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid.

[0028] Suitable salts among those permissible in agriculture and / or physiology are also cationic salts that do not adversely affect the pesticidal and / or parasitic effects of compounds having chemical formula I. Therefore, particularly suitable cations are ions of alkali metals including sodium, potassium, and lithium; ions of alkaline earth metals including calcium and magnesium; and ions of transition metals including manganese, copper, iron, zinc, cobalt, lead, silver, and nickel; as well as ammonium or organic ammonium including monoalkylammonium, dialkylammonium, trialkylammonium, tetraalkylammonium, monoalkenylammonium, dienylammonium, trialkenylammonium, monoynylammonium, diynylammonium, monoalkanolammonium, dialkanolammonium, C5-C6-cycloalkylammonium, piperidinium, morpholinium, pyrrolidineammonium, or benzylammonium; in addition, phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfonium oxide ions, preferably tri(C1-C4-alkyl)sulfonium oxide.

[0029] These compounds of Formula I can exist in various tautomeric forms. This invention covers all such tautomeric forms and mixtures thereof.

[0030] A mixture of diastereomers or racemates of compounds of formula I in free or salt form (obtained depending on the selected starting materials and procedures) can be separated into pure diastereomers or racemates by a known method, for example by stepwise crystallization, distillation and / or chromatography, based on the physicochemical differences of these components.

[0031] Enantiomer mixtures (e.g., racemates) can be obtained by a similar method, in which they can be separated into optically active enantiomers by known methods, such as recrystallization from an optically active solvent; by chiral adsorbent chromatography, such as high-performance liquid chromatography (HPLC) of acetylcellulose; by cleavage with specific immobilized enzymes with the assistance of suitable microorganisms; by the formation of inclusion complexes, such as using chiral crown ethers, when only one enantiomer is a complex; or by conversion into salts of diastereomers, such as by reacting a basic end product racemate with an optically active acid (e.g., a carboxylic acid, such as camphoric acid, tartaric acid, or malic acid, or a sulfonic acid, such as camphorsulfonic acid), and separating the diastereomer mixture that can be obtained in this way (e.g., by stepwise crystallization according to their different solubilities) to give these diastereomers, from which the desired enantiomers can be released by the action of a suitable reagent (e.g., a basic reagent).

[0032] Pure diastereomers or enantiomers can be obtained according to the invention, not only by separating a suitable mixture of isomers, but also by methods of generally known diastereoselective or enantiomeric synthesis, for example by using a suitable stereochemical starting material according to the invention.

[0033] N-oxides can be prepared by reacting the compounds of the present invention with a suitable oxidant (e.g., H₂O₂ / urea adduct) in the presence of an acid anhydride (e.g., trifluoroacetic anhydride). Such oxidations are known from the literature, for example from the Journal of Medicinal Chemistry (J. Med. Chem., 32(12), 2561-73, 1989) or WO00 / 15615 or White, Science (C. White, Science, vol 318, p. 783, 2007).

[0034] If these individual components have different biological activities, it is advantageous to isolate or synthesize, in each case, the biologically more effective isomer, such as an enantiomer or a diastereomer, or a mixture of isomers, such as a mixture of enantiomers or a mixture of diastereomers.

[0035] These compounds having chemical formula I, and their tautomers (in each case in free or salt form) can also be obtained as hydrates if appropriate, and / or include other solvents, such as those that can be used for the crystallization of compounds that exist in solid form.

[0036] This invention also provides a method for preparing piperidine amine compounds containing fused rings, their salts, and N-oxides, comprising the following steps:

[0037] (1) The compound of general formula II or its salt (such as hydrochloride) is coupled with the compound of general formula III to prepare the compound of general formula I. The reaction equation is as follows:

[0038] Alternatively (2) the compound of general formula IV or its salt (such as hydrochloride) is coupled with the compound of general formula V to prepare the compound of general formula I, and the reaction equation is as follows:

[0039] Where L represents halogen, -B(OH)2, or Hal represents halogen, and the substituents R1, R2, R3, R4, X1, X2, X3, X4, X5, X6 and Q are defined as previously stated.

[0040] In one specific embodiment, both reactions (1) and (2) are carried out in the presence of a solvent, a base, and a catalyst.

[0041] In another specific embodiment, a ligand is added to the reactions (1) and (2).

[0042] In another specific embodiment, the solvents for reactions (1) and (2) are selected from at least one of methanol, ethanol, acetonitrile, xylene, tetrahydrofuran, 1,4-dioxane, dichloroethane, N,N-dimethylformamide, dichloromethane, toluene, or water.

[0043] In another specific embodiment, the bases in reactions (1) and (2) are selected from at least one of inorganic or organic bases, such as at least one of K2CO3, Na2CO3, Cs2CO3, NaHCO3, K3PO4, t-BuOK, t-BuONa, EtONa, NaOH, KOH, NaOMe, triethylamine, or DIEA.

[0044] In another specific embodiment, the catalysts for reactions (1) and (2) are selected from at least one of copper salts (such as copper acetate, cuprous oxide, hydrated copper acetate, copper sulfate, copper bromide, etc.) or palladium catalysts (such as palladium, tris(dibenzylacetone)dipalladium, palladium acetate, tetra(triphenylphosphine)palladium, etc.).

[0045] In another specific embodiment, the ligands in reactions (1) and (2) are selected from at least one of 2-(dicyclohexylphosphine)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl (BrettPhos), 2-dicyclohexylphosphine-2',6'-diisopropoxy-1,1'-biphenyl (RuPhos), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (XPhos), 2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl (SPhos), 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (BINAP), or 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos).

[0046] In addition, compounds represented by general formula I can also be prepared by referring to the methods shown in DE4308014A1, CN112745296A, etc.

[0047] The present invention also provides a composition for killing harmful organisms and / or fungi (especially nematodes), comprising a biologically effective amount of at least one of the said fused-ring piperidine amine compound, its salt, and N-oxide.

[0048] In one embodiment, the composition further includes a formulation adjuvant.

[0049] In another embodiment, the composition further includes other active ingredients.

[0050] The present invention also provides a method for controlling harmful organisms and / or fungi (especially nematodes), comprising exposing the harmful organisms and / or fungi (especially nematodes) or their environment to a biologically effective amount of the said fused-ring piperidine amine compound, its salt and N-oxide, or the said composition.

[0051] The present invention also provides the use of the fused-ring piperidineamine compounds, their salts and N-oxides, or the compositions thereof in the control of harmful organisms and / or fungi (especially nematodes).

[0052] Compounds with chemical formula I have been found to be used to control damage caused by pests and / or fungi.

[0053] In one embodiment, a compound having chemical formula I can be used in agriculture.

[0054] Therefore, the present invention further relates to a method for controlling damage and / or yield loss caused by pests and / or fungi, the method comprising applying an effective amount of a compound having chemical formula I to the pest, the site of the pest, or to plants susceptible to pest and / or fungal attack, or to plant propagation material.

[0055] These compounds according to the invention can be used to control, i.e., limit or destroy, harmful organisms and / or fungi that appear, particularly on plants, especially useful and ornamental plants in agriculture, horticulture and forestry, or on the organs of such plants, such as fruits, flowers, leaves, stems, rhizomes, seeds or roots, and in some cases, even on plant organs formed at later times, providing protection against these harmful organisms.

[0056] The compounds of Formula I according to the present invention are active ingredients with preventive and / or therapeutic value in the field of pest control. Even when applied in low doses, they can be used to combat pests and / or fungi resistant to biocides. These compounds of Formula I have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.

[0057] The compounds according to the invention can act on all or individual developmental stages of normally sensitive and resistant animal pests (such as insects or representatives of mites). The insecticidal or acaricidal activity of the compounds according to the invention can be manifested directly, i.e., for example, by the destruction of pests during molting, which occurs immediately or after a period of time; or indirectly, for example, by reducing oviposition and / or hatching rates, with good activity corresponding to a destruction rate (mortality rate) of at least 50%-60%.

[0058] It has now been discovered that compounds of Formula I according to the present invention possess (for practical purposes) a highly advantageous activity spectrum for protecting animals and useful plants against nematode attacks and damage. Therefore, the present invention also makes nematicidal compositions comprising compounds of the present invention, such as those of Formula I, available.

[0059] These compounds with chemical formula I are particularly useful for controlling nematodes. Therefore, in another aspect, the present invention also relates to a method for controlling damage to plants or parts thereof caused by plant-parasitic nematodes (endoparasitic, semi-endoparasitic, and ectoparasitic nematodes), particularly the following plant-parasitic nematodes: root knot nematodes, northern root knot nematode (Meloidogyne hapla), southern root knot nematode (Meloidogyne incognita), Javan root knot nematode (Meloidogyne javanica), peanut root knot nematode (Meloidogyne arenaria), and other Meloidogyne species; cyst-forming nematodes, potato golden nematode (Globodera rostochiensis), and other Globodera species; cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), and beet cyst nematode (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 Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, and Mesocriconema species.Stem and bulb nematodes, *Ditylenchus destructor*, *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. *Needle nematodes*, *Nacobbus* species; *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*, *Radipholus similis* and other *Radipholus* species;*Reniform nematodes*, *Rotylenchus robustus*, *Rotylenchus reniformis*, and other species of the genus *Rotylenchus*; *Scutellonema* species; *Stubby root nematodes*, *Trichodorus primitivus*, and other species of the genus *Trichodorus*, *Paratrichodorus* species; *Stunt nematodes*, *Tylenchorhynchus claytoni*, *Tylenchorhynchus dubius*, and other species of the genus *Tylenchorhynchus*; *Citrus nematodes*, and species of the genus *Tylenchulus*; *Dagger nematode*. This includes species of *Nematodes* and *Xiphinema*, as well as other plant-parasitic nematodes such as *Subanguina* spp., *Hypsoperine* spp., *Macroposthonia* spp., *Melinius* spp., *Punctodera* spp., and *Quinisulcius* spp.

[0060] In particular, the compounds of the present invention can control these nematode species: *Root-knot Nematodes*, *Heterodera*, *Cyclophora*, and *Brief-bodied Nematodes*.

[0061] On another front, the invention also relates to a method for controlling or preventing the infection of useful plants by plant-pathogenic microorganisms, wherein a compound having chemical formula I is applied as an active ingredient to the plant, its parts, or the site thereof. The compounds having chemical formula I according to the invention are distinguished by their activity, good plant tolerance, and environmental safety. They possess highly useful therapeutic, preventative, and systemic properties and are used to protect a wide variety of useful plants. Compounds having chemical formula I can be used to inhibit or destroy diseases occurring on a variety of different useful plants or plant parts (fruits, flowers, leaves, stems, tubers, roots), while also protecting, for example, later-growing plant parts from plant-pathogenic microorganisms. It is also possible to use compounds having chemical formula I as dressing agents for treating plant propagation material, particularly seeds (fruits, tubers, grains) and plant cuttings (e.g., rice), to protect against fungal infection as well as against plant-pathogenic fungi present in the soil.

[0062] Examples of fungi include: Deuteromycetes (e.g., *Botrytis*, *Pyrrosia*, *Helicobacter*, *Fusarium*, *Syneosporium*, *Cercospora*, and *Cladosporium*); Basidiomycetes (e.g., *Rhizoctonia*, *Pythium*, and *Phyllostachys*); Ascomycetes (e.g., *Acer niger*, *Pythium*, *Candida*, and *Uncaria*); Oomycetes (e.g., *Phytophthora*, *Pythium*, and *Monocotyle*); Zygomycetes (e.g., *Rhizopus*); Sterilophyceae, especially those of the genus *Sterilophys*, such as *Synostachys beanus*, also known as Asian soybean rust; and those of the family Sterilophyceae, especially those of the genus *Sterilophys*, such as *Sterilophys gracilis*, also known as stem rust or black rust, a problematic disease in cereals; and *Sterilophys cryptica*, also known as brown rust.

[0063] These plants, and the possible diseases of these plants protected by the method according to the invention, may be mentioned:

[0064] - Wheat, for the control of the following seed diseases: Fusarium (Fusarium solani and Fusarium pink), blackhead (Wheat net smut, Wheat dwarf smut or Wheat Indian smut), strychnoid diseases (Synthia glume), and smut.

[0065] - Wheat, for controlling the following diseases of the aboveground parts of the plant: cereal eye spot (Tapesia yallundae, Tapesia acuiformis), take-all (oat take-all fungus), root blight (Fusarium culmorum, Fusarium graminearum), black spot (Rhizoctonia graminearum), powdery mildew (Erysiphe graminis forma specie tritici), rust (Rhizoctonia gracilis and Rhizoctonia cryptica), and diseases of the genus *Syngonium* (Syngonium leuciscus and Syngonium glomeratum);

[0066] - Wheat and barley are effective in controlling bacterial and viral diseases, such as barley yellow mosaic virus; - Barley is effective in controlling the following seed diseases: net blotch (Cytosporum oryzae, Cytosporum rotundum, and Cytosporum gracilis), loose smut (loose smut), and Fusarium (Fusarium solani and Fusarium oxysporum).

[0067] - Barley is effective in controlling the following diseases of the above-ground parts of the plant: cereal eye spot (Tapesia yallundae), net spot (Erysiphe graminis formas pecie hordei), powdery mildew (Erysiphe graminis formas pecie hordei), dwarf leaf rust (barley stalk rust) and leaf spot (barley cloud spot fungus);

[0068] - Potatoes are effective in controlling tuber diseases (especially potato psoriasis fungus, Phoma tuberosa, Rhizoctonia solani, Fusarium solani), mold (pathogenic Phytophthora), and certain viruses (virus Y).

[0069] - For potatoes, control the following foliar diseases: early blight (Alternaria alternata), mildew (Phytophthora infestans);

[0070] - Cotton, for controlling the following diseases in young plants that grow from seeds: damping-off and blight (Rhizoctonia solani, Fusarium oxysporum) and black root rot (Rhizoctonia solani);

[0071] - Protein-producing plants, such as peas, are beneficial for controlling the following seed diseases: anthracnose (pea brown spot fungus, pea coccidioidomycetes), Fusarium (Fusarium oxysporum), gray mold (Botrytis cinerea), and mildew (pea downy mildew);

[0072] - Oil-bearing plants, such as rapeseed, are used to control the following seed diseases: Brassica stem bud mold, Alternaria brassicae, and Sclerotinia sclerotiorum;

[0073] - Corn, for controlling a variety of seed diseases: (Rhizopus, Penicillium, Trichoderma, Aspergillus and Fusarium graminearum);

[0074] - Flax, for controlling this seed disease: Alternaria linicola;

[0075] - Forest trees are helpful in controlling damping-off disease (Fusarium oxysporum, Rhizoctonia solani);

[0076] - Rice, used to control the following diseases of the above-ground parts: blast (rice blast) and bordered sheath spot (Rhizoctonia solani);

[0077] - Leguminosae plants, for controlling the following diseases of seeds or young plants growing from seeds: damping-off and blight (Fusarium oxysporum, Fusarium oxysporum, Rhizoctonia solani, Pythium spp.);

[0078] - Leguminosae plants, for controlling the following diseases of the above-ground parts: gray mold (Botrytis cinerea), powdery mildew (especially Asteraceae powdery mildew, Cucurbita powdery mildew, and Pepper powdery mildew), Fusarium (Fusarium oxysporum, Fusarium oxysporum), leaf spot (Cladosporium), Cladosporium leaf spot (Cladosporium), anthracnose (Anthracnose), Phytophthora leaf spot (Phytophthora), black spot (Rhizoctonia solani), and mildew (e.g., lettuce downy mildew, Downy mildew, Pseudomonas, Phytophthora);

[0079] - For fruit trees, it helps control various diseases of the above-ground parts: Candida diseases (Monilia fructigenae, M. laxa), scab (Apple black spot fungus), and powdery mildew (Monilia leucocephala); - For vines, it helps control the following leaf diseases: especially gray mold (Botrytis cinerea), powdery mildew (Botrytis cinephala), black rot (Guignardia biwelli), and mildew (Botrytis cinephala).

[0080] - Beetroot is susceptible to the following diseases of the above-ground parts: Cercospora blight (beet brown spot fungus), powdery mildew (beet powdery mildew fungus), and leaf spot (beet leaf spot fungus).

[0081] The fungicidal compositions according to the invention can also be used to combat fungal diseases that readily grow on or inside wood. The term "wood" refers to all types of wood species, and all types of wood intended for construction work, such as solid wood, high-density wood, laminated wood, and plywood. Methods for treating wood according to the invention primarily involve contacting one or more of the compounds of the invention or the compositions according to the invention; this includes, for example, direct application, spraying, soaking, injection, or any other suitable means.

[0082] When used alone, the compounds of the present invention are effective in controlling nematodes, insects, ticks, mites, and / or fungal pathogens in growing or harvested agronomical plants. They can also be used in combination with other bioactive agents used in agriculture, such as one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activators, molluscicides, and pheromones (chemical or biological). Combining the compounds of the present invention, or combinations thereof, in their pest-killing form with other pest-killing agents often results in a broader spectrum of pest-killing activity. For example, these compounds of the present invention having Formula I can be effectively combined or used in combination with compounds such as pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidin, phenoltin compounds, chlorinated hydrocarbons, benzoylphenylurea, pyrroles, and the like.

[0083] By adding, for example, one or more insecticidal, acaricidal, nematicidal, and / or fungicidal active agents, the activity of these compositions according to the invention can be significantly broadened and adapted to the dominant environment. Combinations of compounds having Formula I with other insecticidal, acaricidal, nematicidal, and / or fungicidal active agents can also have further, unexpected advantages, which can be described more broadly as synergistic activity. For example, better plant tolerance, reduced phytotoxicity, control of pests or fungi at different developmental stages, or better behavior during their production (e.g., during grinding or mixing, during storage, or during use).

[0084] The following list of pest control agents, together with compounds that can be used according to the present invention, is intended to illustrate these possible combinations by way of example.

[0085] The following combinations of compounds having chemical formula I with another active compound are preferred (the abbreviation "TX" means "selected from any compound in Table 1 of this invention"):

[0086] An adjuvant, selected from substances composed of free petroleum and TX.

[0087] A miticide selected from the group consisting of: 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenyl sulfone + TX, abamectin + TX, miticide quinone + TX, acetamiprid + TX, flufenoxuron + TX, aldicarb + TX, aldicarb sulfadiazine + TX, α-cypermethrin + TX, cypermethrin + TX, sulfadiazine + TX, aminothiocyanate + TX, chlorpyrifos + TX, chlorpyrifos oxalate + TX, amitraz + TX, dicofol + TX, arsenic trioxide + TX, AVI382 + TX, AZ60541 + TX, azinphos + TX, and azinphos-m ethyl) + TX, azobenzene + TX, azacyclotin + TX, azothoate + TX, benzyl benzoate + TX, benzoxafos + TX, benzoximate + TX, benzyl benzoate + TX, bifenazate + TX, deltamethrin + TX, chlorpyrifos + TX, bromocyclene + TX, bromothion + TX, ethyl bromothion + TX, bromopropylate + TX, thiamethoxam + TX, methyl ethyl methyl sulfonate + TX, butylpyridaben + TX, lime sulfur (calcium) Polysulfide + TX, Campheechlor + TX, Carbanolate + TX, Carbofuran + TX, Carbothiamethoxam + TX, CGA50'439 + TX, Chinomethionat + TX, Chlorbenside + TX, Amitraz + TX, Amitraz Hydrochloride + TX, Brofenoxam + TX, Acaricide + TX, Chlorfenson + TX, Chlorfensulphide + TX, Chlorfenapyr + TX, Ethyl Acetate Chlorobenzol + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chlorpyrifos + TX, methyl chlorpyrifos + TX, chlorthiophos + TX, cinerin I + TX, cinerin II + TX, cinerins + TX, tetradifon + TX, chlorpyrifos + TX, coumarin + TX, crotoxyphos + TX, thiamethoxam + TX,Cyanthoate + TX, fenflurfen [400882-07-7] + TX, deltamethrin + TX, tricyclotin + TX, cypermethrin + TX, DCPM + TX, DDT + TX, demephion + TX, demephion-O + TX, demeton-S + TX, methyl demeton + TX, demeton-O + TX, methyl demeton-O + TX, demeton-S + TX, methyl demeton-S + TX, demeton-S-methylsulphon + TX, abamectin + TX, dialifos + TX, di Phosphine + TX, sulfanilamide + TX, dichlorvos + TX, diflubenzuron + TX, chlorpyrifos + TX, fenpropathrin + TX, dimethoate + TX, dinactin + TX, dinex + TX, dinex-diclexine + TX, dinobuton + TX, dinocap + TX, dinocap-4 + TX, dinocap-6 + TX, dinitrate + TX, dinopenton + TX, dinosulfon + TX, dinotefuran + TX rbon)+TX, dioxin+TX, diphenyl sulfone+TX, disulfiram+TX, ethion+TX, DNOC+TX, dofenapyn+TX, dofenapyn+TX, doxycycline+TX, endothion+TX, EPN+TX, elinochlorfenapyr+TX, ethion+TX, ethoate-methyl+TX, etoxazole+TX, etrimfos+TX, fenazaflor+TX, quinacrine+TX, fenbutatinoxide+TX, fenothiocarb+T X, Cypermethrin + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenson + TX, Fentrifanil + TX, Cypermethrin + TX, Fipronil + TX, Fluacrypyrim + TX, Fluzoral + TX, Flubenzimine + TX, Flufenoxuron + TX, Flucythrinate + TX, Fluenetil + TX, Flufenoxuron + TX, Flumethrin + TX, Flubenside + TXFlupyradifurone + TX, fluvalinate + TX, FMC1137 + TX, amitraz + TX, amitraz hydrochloride + TX, formothion + TX, formoparanate + TX, γ-HCH + TX, glyodine + TX, halfenprox + TX, heptenophos + TX, hexadecylcyclopropane carboxylate + TX, thiamethoxam + TX, iodomethane + TX, isocarbophos + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate + TX, ivermectin + TX Jasmolin I+TX, Jasmolin II+TX, Jodfenphos+TX, Lindane+TX, Lofenuron+TX, Malathion+TX, Malonoben+TX, Mecarbam+TX, Mephosfolan+TX, Thiophanate-methyl+TX, Methacrifos+TX, Phosphate+TX, Chlorpyrifos+TX, Methionine+TX, Dimethoate+TX, Methyl bromide+TX, Metolcarb+TX, Mexacarb+TX, Mexacarb+TX, Mirbemycin+TX, Mirbemycin oxime)+TX, mipafox+TX, phorate+TX, morphothion+TX, moxifloxacin+TX, naled+TX, NC-184+TX, NC-152+TX, nifluridide+TX, nicotinamide+TX, nitrilacarb+TX, nitrilacarb 1:1 zinc chloride complex+TX, NNI-0101+TX, NNI-0250+TX, omethoate+TX, chlorpyrifos+TX, oxydeprofos+TX, sulfonephos ( oxydisulfoton+TX, pp'-DDT+TX, parathion+TX, permethrin+TX, petroleum+TX, fenthion+TX, phorate+TX, phorate+TX, phosfolan+TX, imidacloprid+TX, phosphamidon+TX, phoxim+TX, phorate+TX, methyl pyrimidinium+TX, polychloroterpenes+TX, polynactins+TX, prochloraz+TX, prochloraz+TX, promethazine+TX, promacyl+TX, dicofol+TX, propetamphos+TX, propafenone+TX, propafenone+TXProthidathion + TX, prothoate + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins + TX, pyridaphenthion + TX, pyrimidifen + TX, pyrimiphos + TX, quinalphos + TX, quintiofos + TX, R-1492 + TX, RA-17+TX, Rotenone+TX, Schradan+TX, Sebufos+TX, Selamectin+TX, SI-0009+TX, Sophamide+TX, Spirodiclofen+TX, Spirodiclofen+TX, SSI-121+TX, Sulfuram+TX, Sulfuramid+TX, Sulfotep+TX, Sulfur+TX, S21-121 +TX, flufenoxuron +TX, pyridaben +TX, TEPP +TX, terbam +TX, stiorophos +TX, tetradifon +TX, tetraactin +TX, tetrasul +TX, thiafenox +TX, thiocarboxime +TX, thiofanox +TX, thiometon )+TX, chlorpyrifos+TX, thuringiensin+TX, triamiphos+TX, triarathene+TX, triazophos+TX, triazulon+TX, trichlorfon+TX, trifenofos+TX, trifenactin+TX, phosmet+TX, vaniliprole, and YI-5302+TX,

[0088] An algaecide selected from the group consisting of: 3-benzo[b]thiophene-2-yl-5,6-dihydro-1,4,2-oxathiazine-4-oxide + TX, copper dioctanoate + TX, copper sulfate + TX, cybutryne + TX, dihydronaphthoquinone + TX, dichlorophenol + TX, fentin + TX, quicklime + TX, sodium mancozeb + TX, quinoclamine + TX, quinonamid + TX, simazine + TX, fentin acetate and fentin hydroxide + TX.

[0089] A worm repellent selected from the group consisting of: avermectin + TX, clofentillin + TX, doxorubicin + TX, imamectin + TX, imamectin benzoate + TX, irinotecan + TX, ivermectin + TX, milbemycin + TX, moxifloxacin + TX, piperazine + TX, selamectin + TX, spinosad, and thiophanate + TX.

[0090] A bird killer selected from the group consisting of: chloralose + TX, isodrin + TX, fenthion + TX, pyridine-4-amine and strychnine + TX.

[0091] A bactericide comprising substances selected from the group consisting of: 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalo-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bromonitol + TX, copper dioctanoate + TX, copper hydroxide + TX, cresol + TX, dichlorophenol + TX, dipyrithione + TX, dodexin + TX, fenaminosulfonate + TX, formaldehyde + TX, mercuroquinone + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel di(dimethyl dithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxorubicin + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, chlorothalonil + TX, and thimerosal + TX.

[0092] A biological reagent selected from the group consisting of: *Adoxophyes orana* GV + TX, *Agrobacterium radiolus* + TX, *Amblyseius spp.* + TX, *Anagrapha falcifera* NPV + TX, *Anagrus atomus* + TX, *Aphelinus abdominalis* + TX, *Aphidius colemani* + TX, *Autographa californica* NPV + TX, *Bacillus firmus* + TX, *Bacillus firmus* + TX, *Bacillus sphaericus* Neide + TX, *Bacillus thuringiensis* + TX, *Bacillus thuringiensis* Berliner + TX, *Bacillus thuringiensis* I (Bacillus... Bacillus thuringiensis subsp. aizawai)+TX, Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. israelensis+TX, Bacillus thuringiensis k. (Bacillus thuringiensis subsp. kurstaki)+TX, Bacillus thuringiensis t. (Bacillus thuringiensis subsp.Beauveria bassiana + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella GV + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmoc eruseremicus + TX, Helicoverpa zea + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia Convergences)+TX, Leptomeria dactylopii+TX, Macrorolophus caliginosus+TX, Mamestra brassicae NPV+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae+TX, Neodiprion sertifer NPV and N. truncatella (N. truncatella)Nucleopolyhedrovirus (NPHV) + TX, Small Flower Bug + TX, Paecilomyces fumosoroseus + TX, Pasteurella mite + TX, Pasteuria thornei + TX, Pasteuria nishizawae + TX, Pasteuria ramosa + TX, Chilean Plant Mite (Phytoseiulus persimilis) + TX, Beet Armyworm (Spodopteraexiguamulticapsid) Multinucleated Capsid Nucleopolyhedrovirus + TX, Hairy Nematode (Steinernema bibionis) + TX, Small Roller Moth Steinernema feltiae + TX, Noctuid Moth Steinernema + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp.)+TX, Trichogramma +TX, Typhlodromus occidentalis and Verticillium lecanii+TX.

[0093] A soil disinfectant selected from the group consisting of iodomethane and bromomethane + TX.

[0094] A chemical sterilizing agent selected from the group consisting of: apholate + TX, bisazir + TX, busulfan + TX, diflubenzuron + TX, dimatif + TX, hemel + TX, hempa + TX, metepa + TX, methiotepa + TX, methylapholate + TX, morzid + TX, penfluron + TX, tepa + TX, thiohempa + TX, thiotepa + TX, tratamide, and urethaneimine + TX.

[0095] An insect pheromone selected from the group consisting of: (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tetrate-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicosode-13-en-10-one + TX, (Z) -Tetradecano-7-en-1-al +TX, (Z)-Tetradecano-9-en-1-ol +TX, (Z)-Tetradecano-9-en-1-yl acetate +TX, (7E,9Z)-Dodeca-7,9-dien-1-yl acetate +TX, (9Z,11E)-Tetradecano-9,11-dien-1-yl acetate +TX, (9Z,12E)-Tetradecano-9,12-dien-1-yl acetate +TX, 14-Methyloctadecyl-1-ene +TX, 4-Methylnonanal-5-ol and 4-Methylnonanal-5-one +TX, α-multistriatin +TX, brevicomin +TX, codlelu re)+TX, codlemone+TX, cuelure+TX, disparlure+TX, dodecano-8-en-1-yl acetate+TX, dodecano-9-en-1-yl acetate+TX, dodecano-8+TX, 10-dien-1-yl acetate+TX, dominicalure+TX, ethyl 4-methyloctanoate+TX, eugenol+TX, frontalin+TX, gossyplure+TX, grandlure+TX, grandlure I+TX, grandlure II+TX The following are listed as potential attractants: Hexalure + TX, Ipsdienol + TX, Ipssenol + TX, Japonilure + TX, Lineatin + TX, Litlure + TX, Looplure + TX, Medlure + TX, Megatomoicacid + TX, Methyleugenol + TX, Muscalure + TX, Octadec-2,13-dien-1-ylacetate + TX, Octadec-3,13-Dien-1-ylacetate + TX, Orfralure + TX, Oryctalure + TX, Ostramone + TX, Siglure + TX, Sordidin + TX, Sulcatol + TX, Tetradecanoate-11-en-1-ylacetate + TX, Terfenadine + TX, Terfenadine A + TX, Terfenadine B1 + TX, Terfenadine B2 + TX, Terfenadine C and Trunc-Call + TX,

[0096] An insect repellent selected from the group consisting of: 2-(octylthio)ethanol + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, DEET + TX, DEET + TX, dimethylcarbate + TX, ethylhexanediol + TX, hexane + TX, methoquin-butyl + TX, methylneodecanamide + TX, oxamate, and hydroxymethylbenzene + TX.

[0097] An insecticide selected from the group consisting of: 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-di(4-ethylphenyl)ethane + TX, 1,2-dichloropropane + TX, 1,2-dichloropropane with 1,3-dichloropropene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl-2-ethylsulfinylethylmethyl phosphate + TX, 2-(1,3-dithiacyclopentan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxane-2-yl)phenyl methylcarbamate + TX. Alkyl-2-yl)phenyl ester + TX, 2-(4-chloro-3,5-dimethyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolinone + TX, 2-isovaleryl indan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2-thiocyanoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazole-5-yl dimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-dimethylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate + TX, avermectin + TX, acephate + TX, pyrimidine Amitraz + TX, pyrethroid + TX, acetamiprid + TX, flufenoxuron + TX, acrylonitrile + TX, chlorpyrifos + TX, aldicarb + TX, aldicarb + TX, chlorpyrifos + TX, allethrin + TX, acyclovir + TX, chlorpyrifos + TX, α-cypermethrin + TX, α-ecdysone + TX, aluminum phosphide + TX, cypermethrin + TX, thiophanate-methyl + TX, chlorpyrifos + TX, chlorpyrifos + TX, chlorpyrifos + TX, chlorpyrifos + TX, amitraz + TX, neonicotinoid + TX, ethyl chlorpyrifos + TX, AVI382 + TX, AZ60541 + TX, azadirachtin + TX, methyl pyridinium + TX, ethyl phosphonophosphate + TX, methyl phosphonophosphate + TX, azophos + TX, Bacillus thuringiensis Bacterial δ-endotoxins +TX, barium hexafluorosilicate +TX, barium polysulfide +TX, pyrethroids +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, imidacloprid +TX, carbofuran +TX, chlorpyrifos +TX, β-cypermethrin +TX, β-cypermethrin +TX, bifenthrin +TX, bio-allethrin +TX, bio-allethrin S-cyclopentenyl isomer +TX, bioethanomethrin +TX, bio-permethrin +TX, pyrethroids +TX, di(2-chloroethyl) ether +TX, diflubenzuron +TX, borax +TX, bromopyrethrin +TX, bromophenylenephos +TX, bromoxynil +TX, bromo-DDT +TXBromothion + TX, Bromothion-Ethyl + TX, Carbaryl + TX, Thiamethoxam + TX, Carbaryl + TX, Butathiofos + TX, Butanylcarbide + TX, Butylphosphide + TX, Butanylcarbide Sulfonate + TX, Butylpyridinium + TX, Thiophanate + TX, Calcium Arsenate + TX, Calcium Cyanide + TX, Calcium Polysulfide + TX, Toxaphene + TX, Chlormethrin + TX, Carbofuran + TX, Carbon Disulfide + TX, Carbon Tetrachloride + TX, Trithion + TX, Butylcarbamate + TX, Pyralid + TX, Pyralid Hydrochloride + TX, Sivacrol + TX, Borneol + TX, Chlordane + TX, Kempas + TX, Amitraz + TX, Amitraz Hydrochloride + TX, Phosphorus Oxide + TX, Bromnipotentiol + TX, Poison Fenoxam + TX, Dichlorvos + TX, Chlorpyrifos + TX, Chloroform + TX, Trichloronitromethane + TX, Chlorpyrifos + TX, Pyridine + TX, Chlorpyrifos + TX, Chlorpyrifos-methyl + TX, Chlorfenapyr + TX, Cyclofenac + TX, Cypermethrin I + TX, Cypermethrin II + TX, Cypermethrin + TX, Cis-resmethrin + TX, Cismethrin + TX, Cyper ... TX+, CS708+TX, benzoylphos +TX, phosmet +TX, phosmet +TX, cypermethrin +TX, cypermethrin +TX, deltamethrin +TX, cyhalothrin +TX, deltamethrin +TX, cypermethrin +TX, cypermethrin +TX, cypermethrin +TX, cypermethrin +TX, cyprodinium +TX, phosmet +TX, d-limonene +TX, d-tetramethrin +TX, DAEP +TX, dazomet +TX, DDT +TX, decarbofuran +TX, deltamethrin +TX, phosmet-O+TX, phosmet-S+TX, phosmet +TX, phosmet-methyl +TX, phosmet-O+TX, phosmet-O-methyl +TX, phosmet-S+TX, phosmet-S-methyl +TX, phosmet-S... Phosphate-S-methyl sulfone + TX, diethyl ether urea + TX, chlorpyrifos + TX, diamine phosphate + TX, diazinon + TX, isochlorpyrifos + TX, chlorpyrifos + TX, dichlorvos + TX, didicphos + TX, dicresyl + TX, fenpropathrin + TX, dichlorvos + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, diflubenzuron + TX, dilor + TX, tetrafluoromethrin + TX, methamidophos + TX, dimethoate + TX, dimethoate + TX, methyl chlorpyrifos + TX, difenoconazole + TX, dichlorvos + TX, dicarboxylic acid + TX, dicarboxylic acid-diclexine + TX, proponitrophenol + TX, pendimethalin + TX, danoxin + TXFipronil + TX, Benzyl + TX, Phosphate + TX, Dioxam + TX, Dioxam + TX, Phosphate + TX, Dithiophanate + TX, Dithiophanate + TX, Dithiophanate-methyl + TX, DNOC + TX, Dolantin + TX, DSP + TX, Ecdysone + TX, EI1642 + TX, Abamectin + TX, Abamectin Benzoate + TX, EMPC + TX, Enzyme + TX, Endothiophanate + TX, Indomethacin + TX, Dichlorvos + TX, EPBP + TX, EPN + TX, Juvenile ether + TX, Irinoctyl + TX, Cypermethrin + TX, Etaphos + TX, Ethiophanate-methyl + TX, Ethiophanate + TX Phosphine-methyl + TX, Phosphine + TX, Ethyl formate + TX, Ethyl-DDD + TX, Ethyl dibromide + TX, Ethyl chloride + TX, Ethylene oxide + TX, Permethrin + TX, Ethyl methamidophos + TX, EXD + TX, Ammonium sulfide + TX, Benzophos + TX, Acaricide + TX, Pyrimethanil + TX, Benthiocarb + TX, Fenfluramine + TX, Fenitrothion + TX, Butachlor + TX, Fenoxacrim + TX, Fenoxycarb + TX, Cypermethrin + TX, Cypermethrin + TX, Fenpyrad + TX, Fenoxacrim + TX, Phosphine + TX, Phosphine-ethyl + TX, Cypermethrin + TX, Fipronil + TX, Flupyramide + T X, flufenoxam [272451-65-7]+TX, flucofuron+TX, flucyclopropamide+TX, cypermethrin+TX, diflubenzuron+TX, pyrimethanil+TX, flufenoxuron+TX, trifluralin+TX, flufenoxuron+TX, lambda-cyhalothrin+TX, FMC1137+TX, terbufos+TX, chlorpyrifos+TX, chlorpyrifos+TX, chlorpyrifos hydrochloride+TX, phosmet+TX, formparanate+TX, fenpropathrin+TX, forspazolidinium+TX, thiazolylphosphide+TX, thiazolylphosphide+TX, furazolidone+TX, pyrethrum+TX, γ-cyhalothrin+TX, γ-HCH+TX, biguanide salt+TX, biguanide acetate+TX, GY- 81+TX, Benzyl ether+TX, Chlorfenapyr+TX, HCH+TX, HEOD+TX, Fibuda+TX, Heptenphos+TX, Phosphate+TX, Flufenoxuron+TX, HHDN+TX, Flufenoxuron+TX, Hydrocyanic acid+TX, Acetate +TX, Hyquincarb+TX, Imidacloprid +TX, Propyrimethanil +TX, Indoxacarb +TX, Iodophos +TX, IPSP+TX, Chlorpyrifos +TX, Carbohydrate +TX, Methamidophos +TX, Isofenphos +TX, Transplanting agent +TX, Isoprocarb +TX, O-(Methoxyaminothiophosphoryl)salicylic acid isopropyl ester +TX, Isopyr +TX, Isopyr +TX, Oxazon +TX, Ivermectin +TXJatrophazone I+TX, Jatrophazone II+TX, Iodine Thiophanate +TX, Juvenile Hormone I+TX, Juvenile Hormone II+TX, Juvenile Hormone III+TX, Chlorpentine +TX, Acetylpyridinium +TX, λ-Trichlorofluorocarbonate +TX, Lead Arsenate +TX, Rapirimicarb +TX, Parabromophos +TX, Lindan +TX, Lirimfos +TX, Lufenuron +TX, Thiazolium +TX, m-Isopropylphenyl Methyl Carbamate +TX, Magnesium Phosphate +TX, Malathion +TX, Terfenadine +TX, Azoxystrobin +TX, Phosphate +TX, Tetramethrin +TX, Phosphate +TX, Dimethoate +TX, Mercurous Chloride +TX, Mesulfenfos +TX, Cyfluthrin +TX, Magnesium Phosphate +TX TX, methyl parathion + TX, methyl parathion + TX, chlorpyrifos + TX, methamidophos + TX, methyl sulfonyl fluoride + TX, chlorpyrifos + TX, chlorfenapyr + TX, ethoxyphos + TX, methomyl + TX, tebufenozide + TX, methoxyfenozide + TX, methoxybenzoyl + TX, methyl bromothiocyanate + TX, methyl chloroform + TX, dichloromethane + TX, methoxybenzyl flufenoxuron + TX, cypermethrin + TX, chlorpyrifos + TX, chlorpyrifos + TX, zikcarb + TX, mirtamidophos + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX, pymetrozine + TX X, Naphthalene + TX, NC-170 + TX, NC-184 + TX, Nicotine + TX, Nicotine Sulfate + TX, Flufenoxuron + TX, Acetaminophen + TX, Nithiazine + TX, Cypermethrin + TX, Cypermethrin 1:1 Zinc Chloride Complex + TX, NNI-0101 + TX, NNI-0250 + TX, Nononicotinic Acid + TX, Bisphenylfluorourea + TX, Polyfluorourea + TX, O-5-Dichloro-4-iodophenyl O-ethyl ethyl thiophosphonate + TX, O,O-Diethyl O-4-methyl-2-oxo-2H-chromene-7-yl thiophosphonate + TX, O,O-Diethyl O-6-methyl-2-propylpyrimidin-4-yl thiophosphonate + TX, O,O, O',O'-Tetrapropyl dithiophosphate +TX, Oleic acid +TX, Dimethoate +TX, Carbendazim +TX, Sulfonate-methyl +TX, Isosulfoxide +TX, Sulfonate +TX, pp'-DDT +TX, p-Dichlorobenzene +TX, Parathion +TX, Parathion-methyl +TX, Fluorouracil +TX, Pentachlorophenol +TX, Pentachlorophenyl Laurate +TX, Permethrin +TX, Petroleum oils +TX, PH60-38 +TX, Fenthion +TX, Diphenoxyacetate +TX, Indomethacin +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Thiophanate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate +TX, Phosphate-methyl +TXPirimetaphos+TX, pymetrozine+TX, chlorfenapyr-ethyl+TX, chlorfenapyr-methyl+TX, polyvinyl chloride dicyclopentadiene isomers+TX, polyvinyl chloride terpenes+TX, potassium arsenite+TX, potassium thiocyanate+TX, pyrethrin+TX, prednisolone I+TX, prednisolone II+TX, prednisolone III+TX, primidophos+TX, profenofos+TX, fenpropathrin+TX, pymetrozine+TX, imidacloprid+TX, propiconazole+TX, acetamiprid+TX, propiconazole+TX, propiconazole+TX, propiconazole+TX, ethazolium+TX, propiconazole+TX, propiconazole+TX, protrifenbute+TX, pymetrozine+TX, pyrazophos+TX, pyrazophos-flufenoxam (p yrafluprole+TX, pyrethrin+TX, pyrethrin+TX, pyrethrin I+TX, pyrethrin II+TX, pyrethrin+TX, pyridaben+TX, acetamiprid+TX, pyridaben+TX, pyrimethanil+TX, pyrimethanil+TX, pyriproxyfen+TX, pyriproxyfen+TX, pyriproxyfen+TX, quassia extract+TX, quinalphos+TX, quinalphos-methyl+TX, phosmet+TX, quintiofos+TX, R-1492+TX, rivanyl+TX, pyrethrin+TX, rotenone+TX, RU15525+TX, RU25475+TX, nianna (r Yania)+TX, Rianodin+TX, Saba Veratrum+TX, 8-methylphos+TX, Thiophanate+TX, Selamectin+TX, SI-0009+TX, SI-0205+TX, SI-0404+TX, SI-0405+TX, Flumethrin+TX, SN72129+TX, Sodium Arsenite+TX, Sodium Cyanide+TX, Sodium Fluoride+TX, Sodium Hexafluorosilicate+TX, Sodium Pentachlorophenate+TX, Sodium Selenate+TX, Sodium Thiocyanate+TX, Threshion+TX, Spinosad+TX, Spirodiclofen+TX, Spirotetramethrin+TX, Sulcofuron+TX, Sulcofuron-Sodium+TX, Fipronil+TX, Phoxim+TX, Sulfonyl Fluoride+T X, thiophanate-methyl + TX, tar + TX, τ-flufenoxam + TX, thiamethoxam + TX, TDE + TX, tebufenozide + TX, pyrimethanil + TX, butylpyrimiphos + TX, flufenoxuron + TX, heptafluthrin + TX, dithion + TX, TEPP + TX, cyclopentylpyrethrin + TX, terbam + TX, terbufos + TX, tetrachloroethane + TX, chlorpyrifos + TX, tetramethrin + TX, θ-cypermethrin + TX, thiafenoxam + TX, thiamethoxam + TX, thiophanate-methyl + TX, chlorpyrifos + TX, chlorpyrifos + TX, chlorpyrifos + TX, chlorpyrifos + TX, thiamethoxam + TX, chlorpyrifos + TX, thiamethoxam + TX, chlorpyrifos + TXThiosultap + TX, thiosultap-sodium + TX, Bacillus thuringiensis + TX, chlorfenapyr + TX, tetrabromopyrethrin + TX, tetrafluorobenzyl + TX, transpermethrin + TX, phosmet + TX, azoxystrobin + TX, triazophos + TX, azoxystrobin + TX, trichlorfon + TX, trichlorfon + TX, trichlorfon + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, vaniliprole + TX, veratrine + TX, veratrine + TX, XMC + TX, methomyl + TX, YI-5302 + TX, ζ-cypermethrin + TX, zetamethrin + TX, zinc phosphide + TX, zolaprofos, and ZXI8901 + TX, cyanfenoxam

[7369] 94-63-19]+TX, chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, diflubenzuron [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinosad [187166-40-1+1871] 66-15-0]+TX, Spirotetramethrin [203313-25-1]+TX, Sulfoxaflor [946578-00-3]+TX, Flufiprole [704886-18-0]+TX, Cypermethrin [915288-13-0]+TX, Tetramethylfluthrin [84937-88-2]+TX,

[0098] A molluscicide selected from the group consisting of: di(tributyltin)oxide + TX, bromoacetamide + TX, calcium arsenate + TX, cloethocarb + TX, copper acetylacetate + TX, copper sulfate + TX, triphenyltin + TX, ferric phosphate + TX, metaldehyde + TX, cypermethrin + TX, niclosamide + TX, niclosamide ethanolamine salt + TX, pentachlorophenol + TX, sodium pentachlorophenoxide + TX, tazimcarb + TX, thiamethoxam + TX, tributyltin oxide + TX, trifenmorph + TX, trimethacarb + TX, triphenyltin acetate and triphenyltin hydroxide + TX, pyriprole + TX.

[0099] A nematicide selected from the group consisting of: AKD-3088+TX, 1,2-dibromo-3-chloropropane+TX, 1,2-dichloropropane+TX, 1,2-dichloropropane and 1,3-dichloropropene+TX, 1,3-dichloropropene+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide+TX, 3-(4-chlorophenyl)-5-methylrhodanine+TX, 5-methyl-6-thio-1,3,5-Thiadiazidane-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, abamectin + TX, acetamiprid + TX, malathion + TX, aldicarb + TX, aldoxycarb + TX, AZ60541 + TX, benclothiaz + TX, benzoyl permethrin + TX, butylpyridaben + TX, cadusafos + TX, carbofuran + TX, carbon disulfide + TX, thiocarbofuran + TX, chloropicrin + TX, chlorpyrifos + TX, cloethocarb + TX, cytokinins + TX, dazomet + TX, DBCP + TX, DCIP + TX, diamidoafos + TX, dichlofenthion + TX, didicphos + TX, dimethoate +TX, Imacidine +TX, Imacidine Benzoate +TX, Eprinomectin +TX, Ethoprophos +TX, Dibromoethane +TX, Fenamiphos +TX, Pyridoxine +TX, Fenpyrad +TX, Fosthiazate +TX, Fosthietan +TX, Furfural +TX, GY-81 +TX, Heterophos +TX, Iodimethane +TX, Isamidophos +TX, Isamidophos +TX, Kinetin +TX, Mecarphon +TX, Mecarphon +TX, Magnetonium +TX, Magnetonium Potassium +TX, Magnetonium Sodium +TX, Methyl Bromoethane +TX, Methyl Isothiocyanate +TX, Milbemycin oxime)+TX, moxifloxacin+TX, Myrothecium verrucaria component+TX, NC-184+TX, chlorpyrifos+TX, phorate+TX, phosphocarb+TX, sebufos+TX, selamectin+TX, spinosad+TX, terbam+TX, terbufos+TX, tetrachlorothiophene+TX, thiafenox+TX, thionazin+TX, triazophos+TX, triazuron+TX, xylenol+TX, YI-5302 and zeatin+TX, fluensulfone [318290-98-1]+TX,

[0100] A nitration inhibitor selected from the group consisting of potassium ethyl xanthate and nitrapyrin + TX.

[0101] A plant activator selected from the group consisting of: acibenzolar + TX, acibenzolar-S-methyl + TX, probenazole, and Reynoutria sachalinensis extract + TX.

[0102] A rodenticide selected from the group consisting of: 2-isovalerylindan-1,3-dione + TX, 4-(quinoxalo-2-ylamino)benzenesulfonamide + TX, α-chlorool + TX, aluminum phosphide + TX, antagonist + TX, arsenic trioxide + TX, barium carbonate + TX, bismuth subtilis + TX, bromadiolone + TX, bromadiolone + TX, bromadiolone + TX, calcium cyanide + TX, aldose + TX, chlorpyrifos + TX, vitamin D3 + TX, chlorpyrifos ... Sodium arsenate + TX, Vitamin D2 + TX, Fluorochloride + TX, Fluoroacetamide + TX, Ratidine + TX, Ratidine Hydrochloride + TX, β-HCH + TX, HCH + TX, Hydrogen cyanide + TX, Iodomethacin + TX, Lindane + TX, Magnesium phosphide + TX, Methyl bromide + TX, Ratidine + TX, Phosphate + TX, Phosphine + TX, Warfarin + TX, Potassium arsenite + TX, Warfarin + TX, Onion glycoside + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoroacetate + TX, Strychnine + TX, Thallium sulfate + TX, Warfarin, and Zinc phosphide + TX.

[0103] A synergist selected from the group consisting of: 2-(2-butoxyethoxy)ethyl piperine ester + TX, 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol having nerolidol + TX, MB-599 + TX, MGK264 + TX, synergist ether + TX, synergist aldehyde + TX, synergist ester + TX, S421 + TX, synergist powder (sesamex) + TX, sesasmolin, and sulfoxide + TX.

[0104] An animal repellent selected from the group consisting of: anthraquinone + TX, chloralose + TX, copper naphthenate + TX, copper oxychloride + TX, diazinon + TX, dicyclopentadiene + TX, guazatine + TX, biguanide acetate + TX, cypermethrin + TX, pyridine-4-amine + TX, silane + TX, trimethacarb + TX, zinc naphthenate, and zinc thiram + TX.

[0105] An antiviral agent selected from the group consisting of imannin and ribavirin + TX.

[0106] A wound protectant selected from the group consisting of: mercuric oxide + TX, octhilinone, and methylthiophene + TX.

[0107] And biologically active compounds selected from the group consisting of: azaconazole (60207-31-0]+TX, bifenthrin [70585-36-3]+TX, furazolidone [116255-48-2]+TX, cyclophosphamide [94361-06-5]+TX, difenoconazole [119446-68-3]+TX, tebuconazole [83657-24-3]+TX, flutriafol [106325-08-0]+TX, cyproconazole [114369-43-6]+TX, fluquinazole [136426-54-5]+TX, flusilazole [85509-19-9]+TX, fenazate [76674-21-0]+TX, hexaconazole Alcohol [79983-71-4]+TX, imazalil [35554-44-0]+TX, imazalil [86598-92-7]+TX, tebuconazole [125225-28-7]+TX, tebuconazole [125116-23-6]+TX, cyproconazole [88671-89-0]+TX, isoprothiolane [101903-30-4]+TX, tebuconazole [66246-88-6]+TX, prothioconazole [178928-70-6]+TX, pyrifenox [88283-41-4]+TX, chlorpyrifos [67747-09-5]+TX, propiconazole [60207-90-1]+TX, silflubaconazole (s imeconazole [149508-90-7]+TX, tebuconazole [107534-96-3]+TX, flufenoxuron [112281-77-3]+TX, triadimefon [43121-43-3]+TX, triadimefon [55219-65-3]+TX, fluconazole [99387-89-0]+TX, methamidophos [131983-72-7]+TX, tricyclopyrimidine [12771-68-5]+TX, chloropyrimidine [60168-88-9]+TX, fluorochloropyrimidine [63284-71-9]+TX, bupirimate [41483-43-6]+TX, methylphenidate (dimethirimol)[5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodecyl morpholine[1593-77-7]+TX, fenpropidine[67306-00-7]+TX, butyl morpholine[67564-91-4]+TX, spirocyclam[118134-30-8]+TX, tridemorpholine[81412-43-3]+TX, pyrimethanil[121552-61-2]+TX, pyrimethanil[110235-47-7]+TX, pyrimethanil[53112-28-0]+TXSeed dressing [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl [71626-11-4]+TX, furaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R-metalaxyl [70630-17-0]+TX, furazolidone [58810-48-3]+TX, oxadixyl [77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, debacarb b) [62732-91-6]+TX, Maisuning [3878-19-1]+TX, Thiabendazole [148-79-8]+TX, Chlozolinate [84332-86-5]+TX, Dichlozoline [24201-58-9]+TX, Iprodione [36734-19-7]+TX, Myclozoline [54864-61-8]+TX, Procymidone [32809-16-8]+TX, Vinclozoline [50471-44-8]+TX, Boscalid ( boscalid)[188425-85-6]+TX, [5234-68-4]+TX, [24691-80-3]+TX, [66332-96-5]+TX, [55814-41-0]+TX, [5259-88-1]+TX, [183675-82-3]+TX, [130000-40-7]+TX, [108173-90-6]+TX, [2439-10-3][112-65-2](free bond)+ TX, iminoctadine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX, fenpropathrin [149961-52-4]+TX, tebuconazole {Proc.BCPC,Int.Congr.,Glasgow.2003,1,93}+TX, fluopyram [361377-29-9]+TX, methyl thiophanate [143390-89-0]+TX, fenoxystrobin [133408-50-1]+TX, fenpropathrin [141517-21-7]+TX, fenpropathrin [248593-16-0]+TX, azoxystrobin [117428-22-5]+TXAzoxystrobin [175013-18-0]+TX, ferrous sulfate [14484-64-1]+TX, mancozeb [8018-01-7]+TX, mancozeb [12427-38-2]+TX, mancozeb [9006-42-2]+TX, propineb [12071-83-9]+TX, silane [137-26-8]+TX, zineb [12122-67-7]+TX, ferrous sulfate [137-30-4]+TX, captafol [2425-06-1]+TX, captan [133-06-2]+TX, benzalkonium chloride [1085-98-9]+TX, pyraclostrobin (f luoroimide[41205-21-4]+TX, captan[133-07-3]+TX, toluenesulfonamide[731-27-1]+TX, Bordeaux mixture[8011-63-0]+TX, copper hydroxide[20427-59-2]+TX, copper chloride[1332-40-7]+TX, copper sulfate[7758-98-7]+TX, copper oxide[1317-39-1]+TX, mancozeb[539 88-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX, nitrothal-isopropyl [10552-74-6]+TX, cyprofen [17109-49-8]+TX, iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen [36519-00-3]+TX, pyrazophos [13 457-18-6]+TX, tolclofos-methyl [57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, cymoxanil [101-05-3]+TX, benomyl [413615-35-7]+TX, blasticidin-S [2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX, chlorothalonil [1897-45-6]+TXCycloflufenicol [180409-60-3]+TX, Cymoxanil [57966-95-7]+TX, Dichloronaphthoquinone [117-80-6]+TX, Dicloymet [139920-32-4]+TX, Diclomezine [62865-36-5]+TX, Dicloran [99-30-9]+TX, Diethofencarb [87130-20-9]+TX, Dimethomorph [110488-70-5]+TX, SYP-LI90 (Flumorph) [211867-47-9]+TX Dithianon [3347-22-6] + TX, Ethaboxam [162650-77-3] + TX, Etridiazole [2593-15-9] + TX, Oxadiazon [131807-57-3] + TX, Fenamidone [161326-34-7] + TX, Fenoxanil [115852-48-7] + TX, Fentin [668-34-8] + TX, Ferimzone [89269-64-7] + TX, Fluazinam [ 79622-59-6]+TX, fluopicolide [239110-15-7]+TX, flusulfamide [106917-52-6]+TX, cyclophosphamide [126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol [10004-44-1]+TX, propineb [140923-17-7]+TX, IKF-916 (Cyazofamid) [120116-88-3]+TX, kasugamycin n)[6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, benomyl[220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide[27355-22-2]+TX, polyoxins[11113-80-7]+TX, probenazole[27605-76-1]+TX, propamocarb[25606-41-1]+TX, proquinazid[189278-12-4]+TXPyroquilon [57369-32-1]+TX, Quinoxal [124495-18-7]+TX, Pentachloronitrobenzene [82-68-8]+TX, Thiamethoxam [7704-34-9]+TX, Thiamethoxam [223580-51-6]+TX, Triazine [72459-58-6]+TX, Tricyclazole [41814-78-2]+TX, Azoxystrobin [26644-46-2]+TX, Enteromycin [37248-47-8]+TX, Zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX, isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-bridged methylene-naphthyl-5-yl)-amide (disclosed in WO2007 / 048556)+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4- Carboxylic acid [2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-amide (disclosed in WO2008 / 148570) + TX, 1-[4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetone + TX, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl]piperidin-1-yl]-2 -[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetone [1003318-67-9], both disclosed on page 20 of WO2010 / 123791, WO2008 / 013925, WO2008 / 013622 and WO2011 / 051243)+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-diphenyl-2-yl)-amide (disclosed in WO2006 / 087343)+TX, and 1-methyl-2-(2,4,5-trichloro-thiophene-3-yl)-ethyl]+TX.

[0108] References in square brackets following the active ingredient, such as [3878-19-1], refer to Chemical Abstracts registry numbers. The mixed pairings described above are known, for example, in "The Pesticide Manual" [The Pesticide Manual – A World Compendium; Thirteenth Edition; Editor: CDSTom Lin; The British Crop Protection Council], or in "Compendium of Pesticide Common Names".

[0109] Most of the active ingredients mentioned above are referred to in the text by their so-called “generic name,” the relevant “ISO generic name,” or, in some cases, another “generic name.” If the name is not a “generic name,” the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name,” “traditional name,” “compound name,” or “development code” is used, or if neither of these names nor a “generic name” is used, an “alternative name” is used.

[0110] In each combination, the mass ratio of any two components is selected to give a desired, for example, synergistic effect. Generally, this mass ratio will vary depending on the specific components and the amount of each component present in the combination. Generally, in any combination of the invention, the mass ratio between the two components is independently from each other from 100:1 to 1:100, including ratios 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, 80:2 0, 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, 54:4 6, 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: The preferred mass ratios between any two components of the invention are 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. Preferred mass ratios between any two components of the invention are from 75:1 to 1:75, more preferably 50:1 to 1.50, especially 25:1 to 1:25, advantageously 10:1 refers to 1:10, such as 5:1 to 1:5, for example 1:3 to 3:1. These mixing ratios are understood to include, on the one hand, a mass ratio, and on the other hand, a molar ratio.

[0111] Examples of methods of application of the compounds and compositions thereof used in this invention, namely methods for controlling harmful organisms / fungi in agriculture, such as spraying, atomizing, dusting, brushing, seed dressing, broadcasting, or irrigating - are selected to suit the intended purpose of the environment at the time.

[0112] In agriculture, a preferred method of application is to the leaves of these plants (foliar application), with the frequency and rate of application chosen to match the risk of infection by the pests / fungi discussed. Alternatively, the active ingredient can reach the plant via the root system (systemic absorption), achieved by applying the compound to the site of the plant, for example, by applying a liquid composition of the compound to the soil (through saturation) or by applying the compound in solid form as granules to the soil (soil application). In the case of rice plants, such granules can be metered and added to flooded paddy fields.

[0113] The application rate per hectare is generally 1g to 2000g of active ingredient per hectare, especially 10g / ha to 1000g / ha, preferably 10g / ha to 600g / ha, such as 50g / ha to 300g / ha.

[0114] These compounds and compositions of the present invention are also suitable for the protection of plant propagation material (e.g., seeds, fruits, tubers, or grains, or nursery plants) against the aforementioned types of pests. The propagation material can be treated with the compound before planting; for example, seeds can be treated before sowing. Alternatively, the compound can be applied to the seed grains (coating), which is achieved by immersing the grains in a liquid composition or by applying a layer of solid composition. When the propagation material is planted at the application site, these compositions may also be applied, for example, during row sowing. These methods of treating plant propagation material and the plant propagation material thus treated are further subjects of the present invention. Typically, the treatment rate will depend on the plant to be controlled and the pest / fungus, generally between 1 gram and 200 grams per 100 kg of seeds, preferably between 5 grams and 150 grams per 100 kg of seeds, such as between 10 grams and 100 grams per 100 kg of seeds.

[0115] The term seed includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed tubers, suckers, grains, bulbs, fruits, tubers, cereals, rhizomes, cuttings, cut branches and the like, and in a preferred embodiment refers to true seeds.

[0116] The present invention also includes seeds coated or treated with or containing a compound having Formula I. The term "coated with or treated with and / or containing" generally indicates that, in most cases, the active ingredient is on the surface of the seed when applied, although a portion of the ingredient may penetrate into the seed material, depending on the method of application. When the seed product is (re)planted, it can absorb the active ingredient. In one embodiment, the present invention makes it possible to obtain a plant propagation material having a compound having Formula I adhered thereto. Furthermore, a composition comprising plant propagation material treated with a compound having Formula I is thus obtained.

[0117] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed granulation. The application of a compound having chemical formula I can be achieved by any known method, such as spraying or dusting before or during sowing / planting of these seeds.

[0118] The term "plant" should be understood to also include plants transformed using recombinant DNA technology that are capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those of the genus Bacillus.

[0119] The toxins contained in genetically modified plants make them resistant to harmful insects. These insects can be found in any insect taxonomy, but are particularly common in beetles (Coleoptera), dipterans (Diptera), and butterflies (Lepidoptera).

[0120] Transgenic plants containing one or more genes encoding pesticide resistance and expressing one or more toxins are known, and some of them are commercially available.

[0121] The compounds of the present invention are typically used in the form of a composition comprising a carrier (e.g., a formulation). The compounds and compositions thereof of the present invention can be used in various forms, such as aerosol sprayers, capsule suspensions, cold atomized concentrates, pulverizable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, capsule granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, thermal atomized concentrates, large granules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ULV) liquids, ultra-low volume (ULV) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment, and wettable powders.

[0122] A formulation typically includes a liquid or solid carrier and optionally one or more commonly used formulation aids, which may be solid or liquid, such as non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil, or soybean oil), defoamers, such as silicone oils, preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, adhesives, and / or thickeners. The composition may further include a fertilizer, micronutrient donor, or other product affecting plant growth, and may include a combination comprising the compounds of the present invention and one or more other bioactive agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

[0123] Therefore, the present invention also makes it possible to obtain a composition comprising a compound of the present invention, an agriculturally economical carrier, and optionally one or more commonly used formulation aids.

[0124] These compositions are prepared by methods known per se, in the absence of additives, for example by grinding, sieving, and / or pressing the solid compounds of the present invention, and in the presence of at least one additive, for example by tightly mixing and / or grinding the compound of the present invention with one or more additives. In the case of the solid compounds of the present invention, the grinding / crushing of the compound is to ensure a specific particle size. These methods for preparing these compositions, and the use of these compounds of the present invention for preparing these compositions, are also a subject of the present invention.

[0125] Examples of compositions used in agriculture include emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, direct sprayable or dilutable solutions, coatable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules, or capsules in polymeric substances. These compositions comprise at least one compound according to the invention, and the type of composition is selected to suit the intended purpose and the prevailing environment.

[0126] Examples of suitable liquid carriers are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably C8 to C9. 12 Alkylbenzene moieties, such as xylene mixtures, alkylated naphthalene or tetrahydronaphthalene, aliphatic or alicyclic hydrocarbons, such as paraffin or cyclohexane, alcohols such as ethanol, propanol or butanol, ethylene glycol and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or hexanediol monoethyl ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methylpyrrolidone-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils such as unepoxidized or epoxidized rapeseed oil, castor oil, coconut oil or soybean oil, and silicone oil.

[0127] Examples of solid carriers used for products such as dusts and dispersible powders are typically ground natural minerals such as calcite, talc, kaolin, montmorillonite, or attapulgite. To improve physical properties, it is also possible to add highly dispersed silica or highly dispersed absorbent polymers. Suitable particulate absorbent carriers for granules are porous, such as pumice, gravel, sepiolite, or bentonite, while suitable non-absorbent carrier materials are calcite or sand. Furthermore, a wide variety of granulated inorganic or organic natural materials can be used, particularly dolomite or pulverized plant residues.

[0128] Depending on the type of active ingredient to be formulated, suitable surfactants are nonionic, cationic, and / or anionic surfactants or mixtures of surfactants that possess good emulsifying, dispersing, and wetting properties. The surfactants mentioned below are merely examples; a large number of other surfactants commonly used in formulations and suitable for use according to the present invention are described in the relevant literature.

[0129] Suitable nonionic surfactants are, in particular, polyethylene glycol ether derivatives of aliphatic or alicyclic alcohols, polyethylene glycol ether derivatives of saturated or unsaturated fatty acids, or polyethylene glycol ether derivatives of alkylphenols, which may contain about 3 to about 30 glycol ether groups and about 8 to about 20 carbon atoms in the (cyclic)aliphatic hydrocarbon residues, or about 6 to about 18 carbon atoms in the alkyl moiety of alkylphenols. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol, or alkylpolypropylene glycol (having 1 to about 10 carbon atoms in the alkyl chain and about 20 to about 250 glycol ether groups and about 10 to about 100 propylene glycol ether groups). Typically, each propylene glycol unit of the above compounds contains 1 to about 5 glycol units. Examples that may be mentioned are nonylbenzene alcohol ether, castor oil polyethylene glycol ether, polypropylene glycol / polyethylene oxide adduct, tributylphenoxy polyethylene glycol, polyethylene glycol, or octylphenoxy polyethylene glycol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

[0130] These cationic surfactants are, in particular, quaternary ammonium salts that typically have at least one alkyl residue (about 8 to about 22 C atoms) as a substituent and (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl residues as other substituents. These salts are preferably in the form of halides, methyl sulfates, or ethyl sulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.

[0131] Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surfactant compounds. Examples of suitable soaps are alkali metal salts, alkaline earth metal salts, or (unsubstituted or substituted) ammonium salts of fatty acids having about 10 to about 22 carbon atoms, such as sodium or potassium salts of oleic acid or stearic acid or mixtures of natural fatty acids (obtainable from, for example, coconut oil or tall oil); fatty acid methyl taurine must also be mentioned. However, synthetic surfactants are more commonly used, particularly fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives, or alkyl aryl sulfonates. Typically, these fatty sulfonates and fatty sulfates are alkali metal salts, alkaline earth metal salts, or (substituted or unsubstituted) ammonium salts and they generally have alkyl residues having about 8 to about 22 carbon atoms, alkyl also understood to include an alkyl moiety comprising an acyl residue; examples that may be mentioned are sodium or calcium salts of lignin sulfonate, sodium or calcium salts of dodecyl sulfate, or sodium or calcium salts of mixtures of fatty alcohol sulfates prepared from natural fatty acids. This group also includes sulfate and sulfonate salts of fatty alcohol / ethylene oxide adducts. These sulfonated benzimidazole derivatives preferably contain two sulfonyl groups and fatty acid residues of about 8 to about 22 carbon atoms. Examples of alkylaryl sulfonates are sodium, calcium, or triethanolamine salts of decylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or naphthalenesulfonic acid / formaldehyde condensates. Additionally, suitable phosphates (esters), such as phosphate salts of p-nonylphenol / (4-14)ethylene oxide adducts, or phospholipids, are also possible.

[0132] Typically, these compositions contain 0.1% to 99% (particularly 0.1% to 95%) of the compound according to the invention and 1% to 99.9% (particularly 5% to 99.9%) of at least one solid or liquid carrier. It is also possible, in principle, that 0% to 25% (particularly 0.1% to 20%) of the composition is a surfactant (in each case, % represents a weight percentage). However, for commercial purposes, concentrated compositions are generally preferred, and end users, in principle, use diluted compositions with significantly lower concentrations of the active ingredient.

[0133] Examples of formulation types suitable for barrel mixing compositions include solutions, diluted emulsions, suspensions or mixtures thereof, and dust.

[0134] Regarding the properties of these preparations, the methods of the present invention, such as leafing, wetting, spraying, atomizing, dusting, spreading, coating, or dumping, can be selected according to the intended purpose and the dominant environment.

[0135] This tank-mix formulation composition is generally prepared by diluting one or more premixed compositions containing different biocides and optionally additional adjuvants with a solvent (e.g., water).

[0136] Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technology, such as natural or recycled minerals, solvents, dispersants, wetting agents, thickeners, fillers, adhesives or fertilizers.

[0137] Commercial products are preferably formulated as concentrates (e.g., premixed compositions (formulations)), while end users typically use diluted formulations (e.g., tank-mixed compositions).

[0138] Preferred seed treatment premixes are aqueous suspension concentrates. These premixes can be applied to seeds using conventional processing techniques and machinery, such as fluidized bed technology, drum milling methods, rotostatic seed processors, and rotary drum applicators. Other methods, such as spray beds, can also be useful. The seeds can be pre-coated before coating. After coating, the seeds are typically dried and then transferred to a coating machine for further coating. Such methods are well known in the art.

[0139] In general, the premixed compositions of the present invention comprise 0.5% to 99.9%, particularly 1% to 95%, advantageously 1% to 50% by weight of the desired ingredient, and 99.5% to 0.1%, particularly 99% to 5% by weight of a solid or liquid adjuvant (including, for example, a solvent, such as water), wherein these adjuvants (or adjuvants) may be a surfactant, the amount of which is 0% to 50%, particularly 0.5% to 40% by weight based on the premixed formulation.

[0140] In a preferred embodiment, independent of any other embodiment, a compound having chemical formula I is in the form of a composition for treating (or protecting) plant propagation material, wherein the composition for protecting plant propagation material further comprises a colorant. Such a composition or mixture for protecting plant propagation material may also comprise at least one copolymer of a water-soluble and water-dispersible film-forming polymer that improves the adhesion of the active ingredient to the treated plant propagation material, the polymer having an average molecular weight of at least 10,000 to about 100,000.

[0141] The combination of the present invention (i.e., those including the compounds of the present invention and one or more other bioactive agents) can be administered simultaneously or sequentially.

[0142] In this case, a combination of components is applied sequentially (i.e., one by one), within a mutually reasonable period, to achieve biological performance, such as within hours or days. The order of application of these components in the combination, i.e., whether the compound having chemical formula I should be applied first, is not critical to the implementation of this invention.

[0143] In this case, the components of these combinations are applied simultaneously in the present invention, and they can be applied as a composition containing the combination, wherein (A) the compound having chemical formula I and one or more components of the combination can be obtained from a separate formulation source and mixed together (referred to as a barrel mix, ready-to-use, spray broth, or slurry), or (B) the compound having chemical formula I and one or more components of the combination can be obtained as a separate formulation mixture source (referred to as a premix, i.e., mixture, concentrate, or formulation product).

[0144] In one embodiment, independent of other embodiments, a compound according to the invention is applied as a combination. Therefore, the invention also provides a composition comprising a compound according to the invention as described herein, one or more other bioactive agents, and optionally one or more conventional formulation adjuvants; the composition may be in the form of a barrel-mixed or premixed composition.

[0145] As an alternative to actual synergistic effects with biological activity, these combinations according to the invention can possess unexpectedly advantageous properties, which, more broadly, can be desired as synergistic activities. Examples of such advantageous properties that may be mentioned are: favorable behavior during formulation and / or application (e.g., when grinding, sieving, emulsifying, dissolving, or dispersing); increased storage stability; improved photostability; more favorable degradability; improved toxicological and / or ecotoxicological behavior; or other advantages familiar to those skilled in the art.

[0146] These compounds of the present invention are preferably used as nematicides in agriculture.

[0147] These compounds of the present invention can also be found in other fields, such as the protection of stored goods and storage rooms, the protection of raw materials (such as wood panels and textiles), floor coverings and buildings, and in sanitation management—especially the protection of humans, livestock, and productive livestock against pests. Therefore, the present invention also makes pest-killing compositions for such uses and methods for using them available. The composition for a particular purpose will need to be modified, and those skilled in the art will be able to make such compositions available for any particular purpose.

[0148] In the field of hygiene, the compositions according to the invention are effective against ectoparasites such as hard ticks, soft ticks, scabies mites, fall mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

[0149] These compositions according to the invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cards, leather, flooring and buildings from insect infestation.

[0150] Methods of applying a compound or a combination thereof to stored goods, storage rooms, raw materials (such as wood panels and textiles), floor coverings and buildings, as well as to sanitation management, are known in the art.

[0151] The present invention also provides a method for treating, controlling, preventing and protecting warm-blooded animals (including humans and fish) against infections caused by worms, arachnids and arthropods, both internal and external parasites, the method comprising administering orally, locally or extragastric to the animal an effective amount of a compound having chemical formula I, which is an anthelmintic, acaricide or antiparasitic compound.

[0152] The above methods are particularly useful for controlling and preventing infections caused by worms, nematodes, mites, and internal and external parasites in warm-blooded animals such as cattle, sheep, pigs, camels, deer, horses, poultry, fish, rabbits, goats, mink, foxes, rats, dogs, cats, and humans.

[0153] In the context of controlling and preventing infections in warm-blooded animals, the compounds of the present invention are particularly useful for controlling worms and nematodes. Examples of worms are members of the class Trematoda, commonly referred to as flukes or flatworms, especially members of the genera *Fasciolopsis*, *Fasciolopsis*, *Hemipelia*, *Diplocolumnar*, *Plasmodium*, *Ophisthorchis*, *Fasciolopsis*, *Echinostoma*, and *Paragonimus*. Nematodes that can be controlled by compounds having formula I include *Haemaphysalis*, *Nematoda*, *C. columbarium*, *Oesphagastomu*, *Nematoda*, *Dictyophora*, *Trichuris*, *Filarial*, *Ancyclostoma*, *Ascaris*, and similar genera.

[0154] The compounds of this invention can also control infections of endoparasitic arthropods, such as the larvae of the striped tussock fly and the guttate fly. Furthermore, mites and ectoparasitic arthropod infections in warm-blooded animals and fish, including biting lice, sucking lice, guttate flies, biting flies, muscoid flies, flies, myiasitic fly larvae, gnats, mosquitoes, fleas, mites, ticks, nasal bots, sheep ticks, and chiggers, can be controlled, prevented, or eliminated by these compounds of the present invention. Biting lice include members of the order Trichophagoptera such as cattle lice, dog lice, and sheep lice (Damilina ovis). Sucking lice include members of the order Liceidae such as cattle blood lice, pig blood lice, cattle jaw lice, and buffalo blind lice. Biting flies include members of the genus *Hippophae rhamnoides*. Ticks include members of the genera *Ophiopogon*, *Ixodes*, *Ixodes*, *Ixodes scabra*, *Ixodes scabra*, and *Ixodes scabra*. These compounds of the present invention can also be used to control mites that parasitize warm-blooded mammals and poultry, including mites of the orders Eumetra and Parasitica.

[0155] For oral administration to warm-blooded animals, these compounds of the present invention can be formulated into animal feed, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, veterinary single-dose preparations, gels, tablets, large pills, and capsules. Alternatively, these compounds of the present invention can be administered to animals in their drinking water. For oral administration, the selected dosage form should provide these animals with approximately 0.01 mg / kg to 100 g / kg of the compound of the present invention daily.

[0156] Alternatively, these compounds of the present invention can be administered to animals non-enterally, for example, via rumen, intramuscular, intravenous, or subcutaneous injection. These compounds of the present invention can be dispersed or dissolved in physiologically acceptable carriers for subcutaneous injection. Alternatively, these compounds of the present invention can be formulated as an implant for subcutaneous administration. Furthermore, these compounds of the present invention can be administered to animals transdermally. For non-enteral administration, the selected dosage form should provide these animals with approximately 0.01 mg / kg to 100 mg / kg of the compound of the present invention daily.

[0157] These compounds of the present invention can also be applied topically to these animals in the form of dips, dusts, powders, collars, medallions, sprays, and pour-on formulations. For topical application, dips and sprays typically contain about 0.5 ppm to 5,000 ppm, and preferably about 1 ppm to 3,000 ppm, of the compounds of the present invention. Furthermore, these compounds of the present invention can be formulated for ear tags of animals, particularly tetrapods such as cattle and sheep.

[0158] These compounds of the present invention can also be used in combination with or in combination with one or more other antiparasitic compounds (thereby broadening the activity spectrum), including but not limited to, anthelmintics such as benzimidazole, piperazine, levamisole, thiamethoxam, praziquantel and the like; endectocides such as avermectin, milbemycin and the like; ectoparasite-killing drugs such as arylpyrrole, organophosphates, carbamates; γ-butyric acid inhibitors including fipronil, pyrethroids, spinosad, imidacloprid and the like; insect growth regulators such as pyriproxyfen, cyclopropanediol and the like; and chitin synthase inhibitors such as benzoylurea, including flufenoxuron.

[0159] These parasitic compositions of the present invention comprise an effective amount of one of the compounds of the present invention or a combination thereof with one or more physiologically permissible inert solid or liquid carriers known in veterinary practice for oral, dermal, and topical administration. Such compositions may further include various additives such as stabilizers, defoamers, viscosity modifiers, binders, and thickeners, while commercially available products will preferably be formulated as concentrates, and end-users will typically use diluted formulations.

[0160] These compositions according to the invention can also be used to prepare compositions for the treatment or prevention of fungal diseases in humans and animals, such as mycosis, dermatitis, tinea, and candidiasis, or diseases caused by Aspergillus species such as Aspergillus fumigatus.

[0161] In one embodiment, independent of any other embodiment, the compound having chemical formula I is an anti-worm compound.

[0162] In one embodiment, independent of any other embodiment, the compound having chemical formula I is a pest-killing compound, preferably a nematicide compound. Detailed Implementation

[0163] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0164] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. Specific compound structures and corresponding compound information are shown in Tables 1-2. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0165] Table 1. Compound Structures

[0166] Table 2 Compounds 1 H NMR

[0167] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0168] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown below are either commercially available or can be easily prepared by those skilled in the art.

[0169] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0170] 1. Synthesis of Compound 12

[0171] Compound 12-1 (400 mg, 1.0 eq, 1.6 mmol) was added to a 100 mL single-necked flask, followed by 1,2-dichloroethane, and then trifluoromethylphenylboronic acid 12-2 (334 mg, 1.1 eq, 1.76 mmol), copper acetate (640 mg, 2 eq, 3.2 mmol), and triethylamine (320 mg, 2 eq, 3.2 mmol). The mixture was incubated overnight at 70 °C in a calcium chloride drying tube. The reaction was then analyzed by LC-MS. The reaction solution was poured into water, extracted with dichloromethane, and the organic phase was stirred and filtered through a column. EA (70%) was separated by normal-phase column chromatography. The organic phase was evaporated to dryness to obtain product 12 (50 mg by weight, 98% purity, 7.9% yield).

[0172] 2. Synthesis of Compound 17

[0173] In a 100 mL reaction flask, 12-1 hydrochloride (0.129 g, 1 eq, 0.46 mmol) was dissolved in 5 mL of 1,4-dioxane. Then, 4-difluoromethoxybromobenzene (102 mg, 1 eq, 0.46 mmol), tris(dibenzylacetone)dipalladium (62 mg, 0.15 eq, 0.07 mmol), cesium carbonate (298 mg, 2 eq, 0.92 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyloxanthracene (39 mg, 0.15 eq, 0.07 mmol) were added. After purging with nitrogen three times, the reaction mixture was reacted overnight at 100 °C. After the reaction was complete as monitored by LCMS, the reaction solution was extracted three times with water and ethyl acetate. The organic phase was washed with brine, stirred with silica gel, and separated by normal-phase column chromatography to obtain product 17, weighing 42 mg (purity 91%, yield 23.6%).

[0174] 3. Synthesis of Compound 21

[0175] In a 100 mL reaction flask, 12-1 hydrochloride (0.35 g, 1 eq, 1.24 mmol) was dissolved in 5 mL of 1,4-dioxane. Then, p-bromotrifluoromethylthiobenzene (320 mg, 1 eq, 1.24 mmol), tris(dibenzylacetone)dipalladium (170 mg, 0.15 eq, 0.19 mmol), cesium carbonate (810 mg, 2 eq, 2.48 mmol), and 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (88 mg, 0.15 eq, 0.19 mmol) were added. After purging with nitrogen three times, the reaction mixture was reacted overnight at 100 °C. After the reaction was complete as monitored by LCMS, the reaction solution was extracted three times with water and ethyl acetate. The organic phase was washed with brine, stirred with silica gel, and separated by normal-phase column chromatography to obtain product 21, weighing 38 mg (purity 80%, yield 7.26%).

[0176] 4. Synthesis of compounds 113 and 115

[0177] (1) In a 25 mL single-necked flask, 113-1 (500 mg, 1.0 eq, 1.85 mmol) was added to 10 mL of 1,4-dioxane, followed by the addition of 4-bromo-8-fluoroquinoline (54 mg, 1.0 eq, 1.85 mmol), cesium carbonate (1.8 g, 3.0 eq, 5.55 mmol), and 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (54 mg, 0.05 eq, 0.09 mmol). The mixture was then protected with nitrogen purging, followed by the addition of tris(dibenzylacetone)dipalladium (85 mg, 0.05 eq, 0.09 mmol). The reaction was carried out overnight at 100 °C. After the reaction was complete, the reaction mixture was poured into 20 mL of water, extracted twice with ethyl acetate, and the organic phase was collected. The solution was concentrated under reduced pressure, stirred with silica gel, and separated by normal-phase column chromatography. Product 113 was obtained, weighing 620 mg (purity 97%, yield 76%).

[0178] (2) In a 25 mL single-necked flask, 113 (200 mg, 1.0 eq, 0.53 mmol) was added to 5 mL of ethanol, followed by the addition of an aqueous solution of hydroxylamine (50 wt.%, 105 mg, 3.0 eq, 1.59 mmol). The mixture was reacted overnight at 80 °C. After the reaction was complete, the reaction solution was evaporated to dryness to obtain crude product 115-1, weighing 218 mg (yield 99%).

[0179] (3) In a 25 mL single-necked flask, 115-1 (218 mg, 1.0 eq, 0.53 mmol) was added to 5 mL of dimethyl sulfoxide, followed by dimethyl carbonate (72 mg, 1.5 eq, 0.8 mmol) and sodium hydroxide powder (32 mg, 1.5 eq, 0.8 mmol). The reaction was allowed to proceed overnight at room temperature. After the reaction was complete, the reaction solution was used directly for the next reaction.

[0180] (4) In a 25 mL single-necked flask, add 5 mL of acetonitrile to the reaction solution from the previous step, then add potassium carbonate (220 mg, 3.0 eq, 1.6 mmol) and methyl iodide (114 mg, 1.5 eq, 0.8 mmol). React at room temperature for 2 hours. After the reaction is complete, pour the reaction solution into 100 mL of water, extract twice with ethyl acetate, wash the organic phase twice with saturated brine, collect the organic phase, concentrate under reduced pressure, add silica gel for stirring, and separate by normal-phase column chromatography. Product 115 was obtained, weighing 50 mg (purity 93%, yield 21%).

[0181] Bioactivity evaluation (nematode 96-well plate bioassay):

[0182] (1) Preparation of test reagents

[0183] Accurately weigh the test reagent, dissolve it in DMSO to prepare a stock solution, and dilute it into solutions of different concentration gradients.

[0184] (2) Isolation of target nematodes

[0185] Southern root-knot nematodes: When egg masses emerge from the root nodes, use forceps under a dissecting microscope to remove the egg masses and place them in clean water. Soak them in a 0.25% sodium hypochlorite solution for about 1 minute, then wash and sieve them through a 500-mesh sieve. Place them in a 90mm petri dish containing an appropriate amount of tap water and put them in a sieving device. Incubate at 28℃ for 3 days. The egg masses will then hatch into second-instar larvae. Observe the concentration of the nematode suspension under a microscope and dilute it to a nematode suspension of about 1000 nematodes / mL for later use.

[0186] Mixed-stage pine wood nematodes: Invert a PDA culture medium containing nematodes into a petri dish covered with mycelium. Wash the nematodes off the dish lid with sterile water. Transfer the nematode solution to a new Botrytis cinerea (Glassy mold) petri dish covered with mycelium, 1 mL of nematode solution per dish. Incubate at 25°C in the dark. Once the mycelium has been completely consumed by the nematodes, transfer the solution back to Botrytis cinerea mycelium on the PDA for propagation. Store the cultured nematodes at 4°C. Propagate every 7-10 days, using at least 10 petri dishes each time. Prepare petri dishes where the Botrytis cinerea has been consumed. Wash the nematodes off the dish lid with sterile water. Observe the nematode suspension concentration under a microscope and dilute it to approximately 1000 nematodes / mL for later use.

[0187] (3) Chemical treatment

[0188] Add 100 μL each of the prepared test reagent and nematode suspension to a 96-well culture plate, cover to prevent evaporation, and incubate at 28°C. Include a water control and a reagent control; if a solvent is used, include a solvent control as well.

[0189] (4) Cultivation and Observation

[0190] The nematodes treated with the agent were cultured under normal conditions, and the mortality rate was measured after 72 hours: Mortality rate (%) = (Number of dead nematodes / Number of tested nematodes) * 100. Representative experimental results are shown in Table 3.

[0191] Table 3 Insecticide Test Results

[0192] Note: N represents no data; reference compound A:

[0193] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit good control activity against various types of nematodes, possessing broad-spectrum, high-efficiency, and strong systemic properties. They can effectively control harmful organisms and / or fungi, and thus have certain commercial value.

Claims

1. A piperidineamine compound containing a fused ring, its salt, and its N-oxide: in, X1, X2, X4, X5, X6, R1, R2, R3, R4, and Q independently represent hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, and -N(R) groups, respectively. 21 )2、-CR 21 =N-OR 21 -(CO)N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -S(CO)R 21 -O(CO)OR 21 or-(CO)OR 21 The alkyl, alkenyl, or alkynyl group is optionally selected from halogen, nitro, cyano, cycloalkyl, heterocyclic, aryl, -N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 or -(SO2)R 21 At least one group in it is replaced; X3 represents halogen; R 21 Each can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, aryl, or heterocyclic groups; The aforementioned cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO)R 10 -(SO2)R 10 or -N(R) 10 The ring is substituted by at least one group in )2, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-. R 10 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy. And exclude the following compounds:

2. The piperidine amine compound containing a fused ring, its salt, and its N-oxide according to claim 1, characterized in that, X1, X2, X4, X5, X6, R1, R2, R3, R4, and Q independently represent hydrogen, halogen, nitro, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, heterocyclic, aryl, and -N(R) 21 )2、-CR 21 =N-OR 21 -(CO)N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -S(CO)R 21 -O(CO)OR 21 or-(CO)OR 21 The C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group is optionally selected from halogen, nitro, cyano, C3-C8 cycloalkyl, heterocyclic, aryl, -N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 or -(SO2)R 21 At least one group in it is replaced; R 21 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkylthio-C1-C8 alkyl, C3-C8 cycloalkyl, aryl, or heterocyclic groups. The aforementioned C3-C8 cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO)R 10 -(SO2)R 10 or -N(R) 10 The ring is substituted by at least one group in )2, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-. R 10 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

3. The piperidine amine compound containing a fused ring, its salt, and its N-oxide according to claim 1 or 2, characterized in that, X1, X2, X4, X5, X6, R1, R2, R3, R4, and Q independently represent hydrogen, halogen, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, heterocyclic, aryl, and -N(R) groups, respectively. 21 )2、-CR 21 =N-OR 21 -(CO)N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -S(CO)R 21 -O(CO)OR 21 or-(CO)OR 21 The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally selected from halogen, nitro, cyano, C3-C6 cycloalkyl, heterocyclic, aryl, -N(R) 21 )2、-OR 21 -(CO)R 21 -SR 21 -(SO)R 21 or -(SO2)R 21 At least one group in it is replaced; R 21 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C3-C6 cycloalkyl, aryl, or heterocyclic groups. The aforementioned C3-C6 cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO)R 10 -(SO2)R 10 or -N(R) 10 The ring is substituted by at least one group in )2, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-. R 10 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy. Preferably, the compound is selected from any one of the compounds in Table 1.

4. A method for preparing a piperidine amine compound containing a fused ring as described in any one of claims 1-3, its salt, and its N-oxide, comprising the following steps: (1) Prepared by coupling reaction of the compound of general formula II or its salt (such as hydrochloride) with the compound of general formula III. The reaction equation for compounds represented by general formula I is as follows: Alternatively (2) the compound of general formula IV or its salt (such as hydrochloride) is coupled with the compound of general formula V to prepare the compound of general formula I, and the reaction equation is as follows: Where L represents halogen, -B(OH)2, or Hal represents a halogen, and the substituents R1, R2, R3, R4, X1, X2, X3, X4, X5, X6 and Q are defined as described in any one of claims 1-3; Preferably, reactions (1) and (2) are carried out in the presence of a solvent, a base, and a catalyst; More preferably, a ligand is added to reactions (1) and (2); More preferably, the solvents in (1) and (2) are selected from at least one of methanol, ethanol, acetonitrile, xylene, tetrahydrofuran, 1,4-dioxane, dichloroethane, N,N-dimethylformamide, dichloromethane, toluene, or water; the bases in reactions (1) and (2) are selected from at least one of inorganic or organic bases, such as at least one of K2CO3, Na2CO3, Cs2CO3, NaHCO3, K3PO4, t-BuOK, t-BuONa, EtONa, NaOH, KOH, NaOMe, triethylamine, or DIEA; the catalysts in reactions (1) and (2) are selected from copper salts (such as copper acetate, cuprous oxide, hydrated copper acetate, copper sulfate). The ligands for reactions (1) and (2) are selected from at least one of the following: copper bromide, ...

5. A composition for killing harmful organisms and / or fungi (especially nematodes), characterized in that, The compound comprises at least one of the fused-ring piperidine amine compounds, their salts, and N-oxides as described in any one of claims 1-3, preferably, a formulation adjuvant; more preferably, other active ingredients.

6. A method for controlling harmful organisms and / or fungi (especially nematodes), characterized in that, This includes a biologically effective amount of a piperidine amine compound containing a fused ring as described in any one of claims 1-3, its salts and N-oxides, or the composition described in claim 5, which exposes the harmful organisms and / or fungi (especially nematodes) or their environment to biologically effective amounts.

7. Use of the piperidine amine compound containing a fused ring as described in any one of claims 1-3, its salt and N-oxide, or the composition of claim 5 in the control of harmful organisms and / or fungi (especially nematodes).

Images