Four-membered-ring amide compounds and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and particularly relates to four-membered-ring amide compounds, stereoisomers / isomers / enantiomers / salts and N-oxides thereof and the use thereof. The compounds are shown as general formula I, wherein A1, A2, A3, A4 and A5 each independently represent N or CM; Q represents an aryl group or a heterocyclic group; X represents a halogen; Y represents hydrogen, alkyl or haloalkyl; and R1, R2, R3 and M each independently represent hydrogen, a halogen, nitro, cyano, etc. The compounds have excellent control effects on harmful organisms and / or fungi (especially nematodes).

Description

Four-membered ring amide compounds and their applications Technical Field

[0001] The present invention belongs to the technical field of pesticides, and in particular relates to a four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides and applications thereof. Background Art

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides and fungicides, pests and diseases have acquired resistance, making them difficult to control with existing insecticides and fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term residual properties. Despite the existence of numerous known fungicides and nematicides, such as WO2013143811A1, which discloses N-cyclic amide compounds and their use as nematicides, there remains a need to develop new pest control agents with low toxicity and low residual properties.

[0003] Summary of the Invention

[0004] To solve the above-mentioned problems existing in the prior art, the present invention provides a four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides, which have excellent control effects on pests and / or fungi (especially nematodes).

[0005] The technical solution adopted in the present invention is as follows:

[0006] A four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides:

[0007] wherein A1, A2, A3, A4, and A5 independently represent N or CM;

[0008] Q represents an aryl group or a heterocyclic group;

[0009] X represents halogen;

[0010] Y represents hydrogen, alkyl or haloalkyl;

[0011] R1, R2, R3, and M each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, sulfhydryl, carboxyl, sulfonic acid, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21)2、-O(SO2)N(R 21 )2、-PO(OR 22 )2、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-Si(R 22 )3, -O(CO)R 22 、-O-(SO2)R 22 、-S(CO)R 22 、-(SO2)OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22 、-(CO)OR 22 、-ON=C(R 23 )2. -CR 23 =N-OH or -CR 23 =NOR 22 , wherein the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, nitro, cyano, hydroxyl, thiol, carboxyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO2)R 22 、-(CO)OR 22 、-O(CO)OR 22 、-Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-alkylene-(CO)OH or -O-alkylene-(CO)OR 22 is substituted by at least one group in;

[0012] R 21 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic, -OR 22、-(CO)R 22 、-(CO)OR 22 、-alkylene-(CO)OR 22 、-(SO2)R 22 、-(SO2)OR 22 、-alkylene-(SO2)R 22 、-(CO)N(R 24 )2 or -(SO2)N(R 24 )2;

[0013] R 22 Each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic group, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, cyano, trialkylsilyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic group, -OR 25 、-SR 25 、-O(CO)R 25 、-(CO)R 25 、-(CO)OR 25 OR-O(CO)OR 25 is substituted by at least one group in;

[0014] R 23 Each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl;

[0015] R 24 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl;

[0016] or N(R 21 )2、N(R 24 )2 each independently represents a heterocyclic group wherein the 1-position is a nitrogen atom;

[0017] R 25 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, phenyl, or phenyl substituted by at least one group selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl, phenoxy, or phenoxy substituted by at least one group selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, or haloalkoxy;

[0018] The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-alkylene-(CO)OR 10 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0019] R 10 Each independently represents hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0020] In one embodiment, Y represents hydrogen, C1-C8 alkyl or halogenated C1-C8 alkyl;

[0021] R1, R2, R3, and M each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, sulfhydryl, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2、-PO(OR 22 )2、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-Si(R 22 )3, -O(CO)R 22 、-O-(SO2)R 22 、-S(CO)R 22 、-(SO2)OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22、-(CO)OR 22 、-ON=C(R 23 )2. -CR 23 =N-OH or -CR 23 =NOR 22 , wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, nitro, cyano, hydroxyl, thiol, carboxyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO2)R 22 、-(CO)OR 22 、-O(CO)OR 22 、-Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-(C1-C8 alkylene)-(CO)OH or -O-(C1-C8 alkylene)-(CO)OR 22 is substituted by at least one group in;

[0022] R 21 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic group, -OR 22 、-(CO)R 22 、-(CO)OR 22 、-(C1-C8 alkylene)-(CO)OR 22 、-(SO2)R 22 、-(SO2)OR 22 、-(C1-C8 alkylene)-(SO2)R 22 、-(CO)N(R 24 )2 or -(SO2)N(R 24 )2;

[0023] R 22Each independently represents a C1-C8 alkyl, a C2-C8 alkenyl, a C2-C8 alkynyl, a C3-C8 cycloalkyl, a C3-C8 cycloalkenyl, an aryl or a heterocyclic group, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, cyano, tri-C1-C8 alkylsilyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic group, -OR 25 、-SR 25 、-O(CO)R 25 、-(CO)R 25 、-(CO)OR 25 OR-O(CO)OR 25 is substituted by at least one group in;

[0024] R 23 Each independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxyC1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl;

[0025] R 24 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenylC1-C8 alkyl;

[0026] or N(R 21 )2、N(R 24 )2 each independently represents a heterocyclic group wherein the 1-position is a nitrogen atom;

[0027] R 25 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, phenyl, or phenyl substituted by at least one group selected from the group consisting of halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, phenoxy, or phenoxy substituted by at least one group selected from the group consisting of halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy;

[0028] The aforementioned “C3-C8 cycloalkyl”, “C3-C8 cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-(C1-C8 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0029] R 10 Each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

[0030] In one embodiment, Y represents hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl;

[0031] R1, R2, R3, and M each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2、-PO(OR 22 )2、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-Si(R 22 )3, -O(CO)R 22、-O-(SO2)R 22 、-S(CO)R 22 、-(SO2)OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22 、 -(CO)OR 22 、-ON=C(R 23 )2. -CR 23 =N-OH or -CR 23 =NOR 22 , wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, nitro, cyano, hydroxyl, thiol, carboxyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO2)R 22 、-(CO)OR 22 、-O(CO)OR 22 、-Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-(C1-C6 alkylene)-(CO)OH or -O-(C1-C6 alkylene)-(CO)OR 22 is substituted by at least one group in;

[0032] R 21 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic group, -OR 22 、-(CO)R 22 、-(CO)OR 22 、-(C1-C6 alkylene)-(CO)OR 22 、-(SO2)R 22 、-(SO2)OR 22、-(C1-C6 alkylene)-(SO2)R 22 、-(CO)N(R 24 )2 or -(SO2)N(R 24 )2;

[0033] R 22 Each independently represents a C1-C6 alkyl, a C2-C6 alkenyl, a C2-C6 alkynyl, a C3-C6 cycloalkyl, a C3-C6 cycloalkenyl, an aryl or a heterocyclic group, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, cyano, tri-C1-C6 alkylsilyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic group, -OR 25 、-SR 25 、-O(CO)R 25 、-(CO)R 25 、-(CO)OR 25 OR-O(CO)OR 25 is substituted by at least one group in;

[0034] R 23 Each independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl;

[0035] R 24 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C6 alkyl;

[0036] or N(R 21 )2、N(R 24 ) 2 independently represent unsubstituted or substituted by at least one group selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl

[0037] R 25Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, phenyl or phenyl substituted by at least one group selected from the following: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenoxy or phenoxy substituted by at least one group selected from the following: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy or halo-C1-C6 alkoxy;

[0038] The aforementioned “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-(C1-C6 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0039] R 10 Each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

[0040] In one embodiment, A1, A2, A3, A4, and A5 each independently represent N or CM, and at most two groups are N.

[0041] In the definition of the compounds represented by the above general formula and in all the following structural formulas, the technical terms used, whether used alone or in compound words, represent the following substituents: Alkyl groups with more than two carbon atoms can be straight-chain or branched. For example, the compound word "-O-alkylene-(CO)OR 10" " in which the alkylene 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 is, 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. The term "cycloalkyl" refers to a group consisting of cyclopentyl, cyclohexyl, cyclopentenyl, cyclohex ...

[0042] Unless otherwise specified, the "aryl" mentioned in the present invention includes but is not limited to phenyl, naphthyl, The "heterocyclic group" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups etc., and also include but are not limited to heteroaryl, i.e. an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally fused to a benzo ring, wherein 1 to 4 (e.g. 1, 2, 3 or 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0043] If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different groups selected from the groups mentioned. Furthermore, identical or different substituent characters contained in identical or different substituents are independently selected and may be identical or different. The same applies to ring systems formed from different atoms and units. At the same time, compounds known to those skilled in the art to be chemically unstable under standard conditions are excluded from the scope of the claims.

[0044] In addition, unless otherwise specified, the term "substituted by at least one group" as used herein refers to being substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without a specific connection position can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position as long as it complies with the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group Can represent wait.

[0045] The present invention also provides a four-membered ring amide compound having a cis structure as shown in Formula I', and its stereoisomers / isomers / enantiomers / salts and N-oxides:

[0046] wherein A1, A2, A3, A4, A5, R1, R2, R3, X, Y and Q are as defined above, and They are cis relative to each other on the four-membered ring.

[0047] The present invention also provides a four-membered ring amide compound having a chiral center as shown in Formula I", and its stereoisomers / isomers / enantiomers / salts and N-oxides:

[0048] Wherein, the substituents A1, A2, A3, A4, A5, R1, R2, R3, X, Y and Q are as defined above; the carbon atoms at positions 1 and 2 on the four-membered ring are chiral centers, and have a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R), based on the contents of stereoisomers having R and S configurations at these positions, respectively.

[0049] The present invention also provides a four-membered ring amide compound having a chiral center as shown in Formula I'', and its stereoisomers / isomers / enantiomers / salts and N-oxides:

[0050] Wherein, the substituents A1, A2, A3, A4, A5, R1, R2, R3, X, Y and Q are as defined above; the carbon atoms at positions 1 and 2 on the four-membered ring are chiral centers, and have a stereochemical purity of 60-100% (S), preferably 70-100% (S), more preferably 80-100% (S), further preferably 90-100% (S), and even more preferably 95-100% (S), based on the contents of stereoisomers having R and S configurations at these positions, respectively.

[0051] Here, "stereochemical purity" refers to the percentage of the amount of the stereoisomer in question to the total amount of stereoisomers having a chiral center.

[0052] The compounds of formula I in each case in free form or in salt form, and where appropriate their tautomers, may be present in the form of one of the possible isomers or as a mixture of these, for example in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomer mixtures, such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemic mixtures, depending on the number, absolute and relative configuration of the asymmetric carbon atoms present in the molecule, 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 isomer mixtures and should be understood in this sense in each case above and below, even if no specific stereochemical details are mentioned in each case. The present invention therefore covers all such isomers and tautomers and their mixtures in all proportions, as well as isotopic forms, such as deuterated compounds.

[0053] The present invention also encompasses salts or N-oxides of each compound of formula I.

[0054] Those skilled in the art also understand that because salts of compounds exist in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions, salts also have the biological utility of the non-salt forms.

[0055] Thus, various salts of the compounds of the invention (and active ingredients used in combination with the active ingredients of the invention) can be used to control invertebrate pests and animal parasites. Agriculturally and / or physiologically acceptable salts 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.

[0056] Suitable salts include salts of cations which do not adversely affect the pesticidal and / or parasiticidal action of the compounds of formula I. Suitable cations are therefore particularly alkali metal ions, including sodium, potassium and lithium, alkaline earth metal ions, including calcium and magnesium, and transition metal ions, including manganese, copper, iron, zinc, cobalt, lead, silver, nickel, and ammonium or organoammonium ions, including monoalkylammonium, dialkylammonium, trialkylammonium, tetraalkylammonium, monoalkenylammonium, dialkenylammonium, trialkenylammonium, monoalkynylammonium, dialkynylammonium, monoalkanolammonium, dialkanolammonium, C5-C6-cycloalkylammonium, piperidinium, morpholinium, pyrrolidinium or benzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.

[0057] The compounds of formula I can exist in different tautomeric forms. The present invention encompasses all those tautomeric forms and mixtures thereof.

[0058] Mixtures of diastereomers or racemates of compounds of formula I in free or salt form, the availability of which may depend on the starting materials and procedures chosen, can be separated into the pure diastereomers or racemates by a known method on the basis of the physicochemical differences of the components, for example, by fractional crystallization, distillation and / or chromatography.

[0059] Enantiomeric mixtures (e.g. racemates) can be obtained by a similar process and can be resolved into the optical antipodes by known methods, for example, by recrystallization from optically active solvents; by chromatography on chiral adsorbents, for example high performance liquid chromatography (HPLC) on acetylcellulose; by cleavage using specific immobilized enzymes with the aid of suitable microorganisms; in the case where only one enantiomer is complexed, via the formation of an inclusion complex, for example using chiral crown ethers; or by conversion into diastereomeric salts, for example by reacting a basic end product racemate with an optically active acid (e.g. a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid) and separating the diastereomeric mixtures obtainable in this way (e.g. by fractional crystallization based on their different solubilities) to give the diastereoisomers from which the desired enantiomer can be liberated by the action of a suitable reagent (e.g. a basic reagent).

[0060] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomer mixtures, but also by generally known diastereoselective or enantioselective synthesis methods, for example by carrying out the method according to the invention using starting materials of an appropriate stereochemistry.

[0061] N-oxides can be prepared by reacting a compound of the invention with a suitable oxidizing agent (e.g. H O / urea adduct) in the presence of an anhydride (e.g. trifluoroacetic anhydride). Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 00 / 15615 or C. White, Science, vol 318, p. 783, 2007.

[0062] If the individual components have different biological activities, it is advantageous to isolate or synthesize the biologically more effective isomer, such as an enantiomer or diastereomer, or isomer mixtures, such as enantiomeric mixtures or diastereomeric mixtures, in each case.

[0063] The compounds of formula I and, where appropriate, their tautomers (in each case in free form or salt form) can, if appropriate, also be obtained in the form of hydrates and / or include other solvents, such as those which can be used for the crystallization of compounds present in solid form.

[0064] The present invention also provides a method for preparing a four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides, comprising the following steps:

[0065] (1) The compound represented by the general formula II is subjected to a condensation reaction with the compound represented by the general formula III to obtain the compound represented by the general formula I. The reaction equation is as follows:

[0066] Alternatively, (2) Compound IV and Compound V are coupled to obtain Compound I, and the chemical reaction equation is as follows:

[0067] Wherein, either Z1 or Z2 represents a halogen, and the other represents Substituents A1, A2, A3, A4, A5, R1, R2, R3, X, Y and Q are as defined above.

[0068] In one embodiment, the reaction of steps (1) and (2) is carried out in the presence of a solvent.

[0069] In another embodiment, a condensing agent and / or a base is added during the reaction of step (1).

[0070] In another embodiment, a catalyst and / or a base is added in step (2).

[0071] In another specific embodiment, the solvent in steps (1) and (2) is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran, ethyl acetate or water.

[0072] In another specific embodiment, the base in steps (1) and (2) is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.) or an organic base (such as DMAP, pyrazole, triethylamine, DIEA, etc.).

[0073] In another embodiment, the condensing agent in step (1) is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU.

[0074] In another specific embodiment, the catalyst in step (2) is selected from at least one of Pd(dppf)Cl2, Pd(PPh3)4, PdCl2, Pd(OAc)2, Pd(PPh3)2Cl2, NiCl2(dppf) and PdCl2(dppf)·CH2Cl2 (CAS No.: 95464-05-4).

[0075] In addition, the compound represented by general formula I can also be prepared by referring to the methods shown in WO2015003951 A1, WO2013143811A1, etc.

[0076] The present invention also provides a composition for killing pests and / or fungi (especially nematodes), comprising a biologically effective amount of the four-membered ring amide compound, at least one of its stereoisomers / isomers / enantiomers / salts and N-oxides.

[0077] In one embodiment, the composition further comprises a formulation adjuvant.

[0078] In another embodiment, the composition further comprises other active ingredients.

[0079] The present invention also provides a method for controlling pests and / or fungi (especially nematodes), comprising contacting the pests and / or fungi or their environment with a biologically effective amount of the four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides or the composition.

[0080] The present invention also provides use of the four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides or the composition in preventing and controlling harmful organisms and / or fungi (especially nematodes).

[0081] It has been found that the compounds of formula I, I', I" or I'" are useful for controlling damage caused by pests and / or fungi.

[0082] In one embodiment, the compound of Formula I, I', I", or I'" can be used in agriculture.

[0083] The present invention is therefore furthermore directed to a method for controlling damage and / or yield losses caused by pests and / or fungi, which method comprises applying an effective amount of a compound of formula I, I', I" or I'" to the pest, to the locus of the pest, or to a plant susceptible to attack by pests and / or fungi or to plant propagation material.

[0084] The compounds according to the invention can be used for controlling, i.e. limiting or destroying, harmful organisms and / or fungi which occur in particular on plants, especially on useful and ornamental plants in agriculture, horticulture and forestry, or on organs of such plants, such as fruits, flowers, leaves, stalks, rhizomes, seeds or roots, and in some cases even on plant organs formed at a later point in time, for protection against these harmful organisms.

[0085] The compounds of the formula I, I', I" or I'" according to the invention are active ingredients of preventive and / or therapeutic value in the field of pest control. Even when applied at low application rates, they can be used to combat pests and / or fungi that are resistant to pesticides. The compounds of the formula I, I', I" or I'" have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.

[0086] The compounds according to the invention can act on all or individual developmental stages of normally sensitive and also resistant animal pests (such as insects or representatives of the order Acarina). The insecticidal or acaricidal activity of the compounds according to the invention can manifest itself directly, i.e., for example, by the destruction of the pests during molting, which occurs immediately or after a certain period of time, or indirectly, for example, by a reduction in egg laying and / or hatching rates, good activity corresponding to a destruction rate (mortality) of at least 50% to 60%.

[0087] It has now been found that the compounds of the formula I, I', I" or I'" according to the invention have (for practical purposes) a very advantageous spectrum of activity for protecting animals and useful plants against attack and damage by nematodes. The present invention therefore also makes available nematicidal compositions comprising the compounds of the invention, such as the formula I, I', I" or I'".

[0088] The compounds of formula I are particularly useful for the control of nematodes. In another aspect, the present invention therefore also relates to a method for controlling damage to plants or parts thereof caused by plant-parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes), in particular the following plant-parasitic nematodes, such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; cereal cyst nematodes, Heterodera avenae, Heterodera glycines, Heterodera schachtii and Heterodera schachtii. 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, 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, Radopholus similis, and other Radopholus species;Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis, and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus, and other Trichodorus species; Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes), Xiphinema species; and other plant-parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.;

[0089] In particular, the nematode species: Meloidogyne, Heterodera, Coelenteroides and Pratylenchus can be controlled by the compounds according to the invention.

[0090] Examples of animal pests are:

[0091] - from the order Acarina, for example,

[0092] Acalitus spp., Acaricalus spp., Aceria spp., Acarina ...

[0093] - from the order Phthirus, for example,

[0094] Haematoptes, Longignatus, Human lice, Pemphigoids, and Psyllids;

[0095] - from the order Coleoptera, e.g.

[0096] Amphimallon majale, Amphimallon majale, Oriental beetle, Amphimallon majale, Astylus atromaculatus, Ataenius spp., Atomaria linearis, Beet flea beetle, Cerotoma spp., Single leaf beetle, Root neck beetle, Green beetle, Curculionidae, Rhinoceros beetle, Rhinoceros beetle, Root firefly beetle, Diloboderus abderus, Eremnus spp., Black sugarcane beetle, Coffee berry borer, Lagria vilosa, Potato beetle, Rice water beetle, Liogenys spp., Maecolaspis spp., Chestnut velvet beetle, American leaf beetle (Megascelis spp.), Melighetes aeneus, Myochrous beetle, armatus, saw-beetle spp., Otiorhynchus spp., horn beetle spp., spotted beetle spp., beetle spp., rape flea beetle spp., Rhyssomatus aubtilis, root beetle spp., scarab beetle, rice weevil spp., wheat moth spp., pseudo-root beetle spp., pointed cryptomonas spp., soybean stem beetle, ground beetle spp., castanea spp., and trophoderm beetle spp.;

[0097] - from the order Diptera, e.g.

[0098] Aedes spp., Anopheles spp., Sorghum fruit fly, Bactrocea oleae, Garden midge, Bradysia spp., Red-headed blowfly, Bactrocera spp., Chrysomelidae spp., Culex spp., Yellow fly, Bactrocera spp., Ground fly, Drosophila melanogaster, Toilet fly, Gastrocera spp., Geomyza tripunctata, Glossina spp., Desmodium spp., Lipid fly, Liriomyza spp., Lucilia spp., Liriomyza spp., Housefly spp., Mylomyia spp., Swedish straw fly, Spring fly, Grass fly spp., Bactrocera spp., Riveria quadrifasciata, Scatella spp., Fungus gnat, Bitefly spp., Tabanus spp., Tapeworm spp., and Crane spp.;

[0099] - from the order Hemiptera, e.g.

[0100] Acanthocoris scabrator, Green stink bug, Alfalfa blind bug, Amblypelta nitida, Bathycoelia thalassina, Soil stink bug, Cockspur, Clavigralla tomentosicollis, Creontiades spp., Cocoa stink bug, Dichelops furcatus, Cotton stink bug, Edessa spp., Euchistus spp., Eurydema pulchrum, Flat shield bug, Brown-winged stink bug, Horcias nobilellus, Rice stink bug, Lygus, Tropical scale, Murgantia histrionic), Neomegalotomus spp., Nesidiocoris tenuis, Green stink bug, Nysius simulans, Oebalus insularis, Skin stink bug, Wall stink bug, Red assassin bug, Cocoa stink bug, Scaptocoris castanea, Black stink bug (Scotinophara spp.), Thyanta spp., Triatomine bug, Cassava web bug (Vatiga illudens);

[0101] - from the order Homoptera, e.g.

[0102] Aphids, Adalges spp., Agallina ensigera, Agonascena targionii, Aleurodicus spp., Aleurocanthus spp., Sugarcane hole whitefly, Aleurothrixus floccosus, Cabbage whitefly (Aleyrodes brassicae), Cotton leafhopper (Amarasca biguttula), Yellow-circled sawfly (Amritodus atkinson), Kidney-shielded scale, Aphididae, Aphid, Scale (Aspidiotus spp.), Eggplant groove aphid, Bactericera cockerelli, Aleurodicus spp., Brachycaudus spp., Cabbage aphid, Cavariella spp., Two-tailed aphid (Cavariella aegopodii) Scop.), Lecanus spp., Brown Scale, Net-seed Grass Leaf Scale, Cicadella spp., Cofana spectra, Cryptomelania spp., Cicadulina spp., Brown Soft Scale, Corn Yellow-winged Leafhopper, Whitefly spp., Citrus Psyllid, Wheat Aphid, Western Aphid, Small Green Leafhopper, Apple Aphid, Grape Leafhopper spp., Wax Clam spp., Glycaspis brimblecombei, Cabbage Aphid, Hyalopterus spp., Super-tumor Aphid species, Lemon Green Leafhopper (Idioscopus clypealis), Jacobiasca lybica, Laodelphax striatum, Ball-hard Scale, Oyster Shield Scale, Lopaphis erysimi, Lyogenys maidis, Longitudinal Aphid, Mahanarva spp., Metcalfa pruinosa), wheat aphid, Myndus crudus, aphid spp., Taiwan leek aphid, black-tailed leafhopper spp., brown planthopper (Nilaparvata spp.), pear green aphid, Odonaspis ruthae, parasitic sugarcane woolly aphid, bayberry whitefly, Caulis psyllid, scutellaria spp., gall aphid spp., corn waxhopper, flat-horned planthopper spp., hopscotch aphid, phylloxera spp., Mosella spp., white-shielded scale spp., mealybug spp., cotton blind bug (Pseudatomoscelis seriatus), psyllid spp., cotton scale (Pulvinaria aethiopica), round-shielded scale spp., Quesada gigas, electric leafhopper (Recilia dorsalis), constrictor aphid spp., black-helmeted scale spp., leafhopper spp., dichotomous aphid spp., wheat aphid (Sitobion spp.)), white-backed planthopper, Spissistilus festinus, Tarophagus proserpina, aphids, whiteflies, Tridiscus sporoboli, Trionymus spp., African psyllids, orange-headed scale, Zygina flammigera, Zyginidia scutellaris;

[0103] - from the order Hymenoptera, e.g.

[0104] Arge spp., Arge spp., Argetotermes ...

[0105] - from the order Isoptera, e.g.

[0106] Coptotermes, Corniternes cumulans, Coptotermes, Macrotermes, Macrotermes, Microtermes, Reticulitermes; tropical fire ants

[0107] - from the order Lepidoptera, e.g.

[0108] Long-winged torrefies, brown-banded torrefies, clear-winged torrefies, ground moths, cotton leafworms, Amylois spp., pea moths, yellow torrefies, silver moths (Argyresthia spp.), banded torrefies, yarrow-patterned torrefies, cotton miners, corn borers, powdery moths, peach fruit moths, grass borers, leaf rollers, Chrysoteuchia topiaria, grape fruit moths, leaf rollers, cloud torrefies, pattern torrefies, sheath moths, lepidoptera, Cosmophila flava, grass borers, cabbage borers, apple torrefies, boxwood moths, torrefies, boxwood moths, stem borers, Sudan bollworms, diamond borers, African stem borers, powdery moths, leaf torrefies (Epinotia) spp.), fine-spotted lantern moth, Etiella zinckinella, flower tortoise spp., ring-needle moth, yellow tussock moth spp., root cutter spp., Feltia jaculiferia, Grapholita spp., green budworm moth, Spodoptera spp., cabbage borer, Herpetogramma spp., American white moth, tomato borer, Lasmopalpus lignosellus, spiral leafminer, leafminer spp., grape flower tortoise, Loxostege bifidalis, tussock moth spp., miner spp., leaf miner spp., cabbage armyworm, tobacco hornworm, Mythimna spp., Noctuidae spp., fall geometre spp., Orniodes indica, European corn borer, super-small tortoise spp., brown tortoise spp., small-eyed tortoise spp., stem borer, Pectinophora gossypiela, coffee leafminer, armyworm, potato moth, cabbage butterfly, Pieris spp., diamondback moth, budworm spp., leaf moth spp., mint leafminer, Richia albicosta, Scirpophaga spp., stem borer, stalkworm, Spodoptera spp., cotton leaf roller, stalkworm, Heteroptera spp., leaf roller, cabbage looper, tomato leafminer, and brood moth spp.;

[0109] - from the order Maophaga, e.g.

[0110] Damalina spp. and Trichodesmosis spp.;

[0111] - from the order Orthoptera, e.g.

[0112] Blatta, Blattella, Mole Cricket, Madeira Cockroach, Locust, American Mole Cricket (Neocurtilla hexadactyla), Periplaneta, Scapteriscus spp., and Desert Locust;

[0113] - from the order Rodentia, for example,

[0114] Booklice;

[0115] - from the order Siphonaptera, e.g.

[0116] Ceratophyllum, Ctenophora and Xenophora;

[0117] - from the order Thysanoptera, for example,

[0118] Calliothrips phaseoli, Flower Thrips spp., Sun Thrips spp., Brown-banded Thrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Banded Thrips spp., Thrips spp.;

[0119] - from the order Thysanura, e.g.

[0120] Silverfish.

[0121] In another aspect, the present invention also relates to a method for controlling or preventing infection of useful plants by phytopathogenic microorganisms, wherein a compound of the formula I, I', I" or I'" is applied as an active ingredient to the plants, parts thereof or the locus thereof. The compounds of the formula I, I', I" or I'" according to the invention are distinguished by their activity, good plant tolerance and environmental safety. They have very useful therapeutic, preventive and systemic properties and are used for protecting a wide variety of useful plants. The compounds of the formula I, I', I" or I'" can be used to inhibit or destroy diseases that occur in plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of a wide variety of useful plants, while also protecting, for example, those plant parts that grow later from phytopathogenic microorganisms. It is also possible to use the compounds of formula I, I', I" or I'" as dressing agents for treating plant propagation material, in particular seeds (fruits, tubers, grains) and plant cuttings (e.g. rice), for protection against fungal infestation as well as against phytopathogenic fungi present in the soil.

[0122] Examples of fungi include: the class Deuteromycetes (e.g., Botrytis, Pyrospora, Helminthosporium, Fusarium, Septoria, Cercospora, and Alternaria); the class Basidiomycetes (e.g., Rhizoctonia, Puccinia, Puccinia); the class Ascomycetes (e.g., Venturia and Powdery Mildew, Monocystis, Moniliformis, Uncinaria); the class Oomycetes (e.g., Phytophthora, Pythium, Monoparagus); the class Zygomycetes (e.g., Rhizopus); the family Pucciniaceae, particularly those of the genus Pucciniaceae, such as Puccinia pachyrhizi, which is also known as Asian soybean rust, and those of the family Pucciniaceae, particularly those of the genus Pucciniaceae, such as Puccinia graminis, also known as stem rust or black rust, which is a problem disease in cereals, and Puccinia recondita, also known as brown rust.

[0123] Among the plants and possible diseases of these plants which can be protected by the method according to the invention, mention may be made of:

[0124] - Wheat, for the control of the following seed diseases: Fusarium (Fusarium spp. and Fusarium rosobacterium), black bunt (Tilletia tritici, Tilletia dwarfii, or Tilletia indica), Septoria (Septoria glumae), and loose smut;

[0125] - wheat, for the control of the following diseases of the above-ground parts of the plant: cereal eye spot (Tapesia yallundae, Tapesia acuiformis), take-all (Tapesia taecii), root blight (F. culmorum, F. graminearum), black spot (Rhizoctonia graminearum), powdery mildew (Erysiphe graminis forma specie tritici), rust (Puccinia striatum and Puccinia reclusa), and Septoria diseases (Septoria tritici and Septoria glume);

[0126] - wheat and barley, for the control of bacterial and viral diseases, such as barley yellow mosaic; - barley, for the control of the following seed diseases: net blotch (Pyricularia trichomoniasis, Pyricularia terrestris, and Cochliobolus graminis), loose smut (loose smut), and fusarium (Fusarium nivale and Fusarium roseum);

[0127] - barley, for the control of the following diseases of the above-ground parts of the plant: cereal eye spot (Tapesia yallundae), net blotch (Pyricularia teres and Cochlosporium graminis), powdery mildew (Erysiphe graminis formas pecie hordei), dwarf leaf rust (Puccinia hordei) and leaf spot (Puccinia hordei);

[0128] - Potatoes, for the control of tuber diseases (particularly Aralia solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani), mildew (Phytophthora infestans) and some viruses (Virus Y);

[0129] - Potatoes, for the control of the following foliar diseases: early blight (Alternaria solani), mildew (Phytophthora infestans);

[0130] - Cotton, for the control of the following diseases in young plants grown from seed: damping-off and blight (Rhizoctonia solani, Fusarium oxysporum) and black root rot (Thalassemia radicifolia);

[0131] - protein-producing plants, such as peas, for controlling the following seed diseases: anthracnose (Psoralea corylifolia, Mycosphaeria pisum), fusarium (Fusarium oxysporum), gray mold (Botrytis cinerea) and mildew (Peronospora pisum);

[0132] - Oilseed rape, for the control of the following seed diseases: Stenotrophomonas brassicae, Alternaria brassicae, and Sclerotinia sclerotiorum;

[0133] - Corn, for the control of various seed diseases (Rhizopus, Penicillium, Trichoderma, Aspergillus, and Gibberella);

[0134] - Flax, for controlling this seed disease: Alternaria linicola;

[0135] - Deep forest trees, for controlling damping-off disease (Fusarium oxysporum, Rhizoctonia solani);

[0136] - Rice, for the control of the following diseases of above-ground parts: blast (Pyricularia oryzae), bordered sheath spot (Rhizoctonia solani);

[0137] - Leguminous plants, for the control of the following diseases on seeds or young plants grown from seeds: damping-off and blight (Fusarium oxysporum, Fusarium roseum, Rhizoctonia solani, Pythium spp.);

[0138] - Leguminous plants, for the control of the following diseases on aerial parts: gray mold (Botrytis spp.), powdery mildew (especially Erysiphe spp., Erysiphe spp. and Pyrophila spp.), Fusarium spp. (Fusarium oxysporum, Fusarium rosporum), leaf spot (Cladosporium spp.), Alternaria leaf spot (Alternaria spp.), anthracnose (Colletotrichum spp.), Septoria leaf spot (Septoria spp.), black spot (Rhizoctonia solani), mildew (for example, Downy mildew of lettuce, Peronospora spp., Pseudocoperonospora spp., Phytophthora spp.);

[0139] - fruit trees, for the control of various diseases of aerial parts: candidiasis (Monilia fructigenae, M. laxa), scab (Viburnum indica), powdery mildew (Monilia albicans); - vines, for the control of the following foliar diseases: in particular gray mold (Botrytis cinerea), powdery mildew (Uncinaria officinalis), black rot (Guignardia biwelli) and mildew (Plasmopara viticola);

[0140] Beetroot for the following diseases of aerial parts: cercospora blight (brown blight of beet), powdery mildew (Erysiphe beticola), leaf spot (Erysiphe beticola).

[0141] The fungicidal compositions according to the invention can also be used to combat fungal diseases that are susceptible to growth on or in wood. The term "wood" refers to all types of wood species, as well as all types of wood intended for construction work, such as solid wood, high-density wood, laminated wood, and plywood. The method for treating wood according to the invention essentially involves contacting with one or more compounds according to the invention or compositions according to the invention; this includes, for example, direct application, spraying, immersion, injection, or any other suitable means.

[0142] When used alone, the compounds of the present invention are effective in controlling nematodes, insects, acarid pests, and / or fungal pathogens of growing or harvested agronomic plants. They can also be used in combination with other bioactive agents used in agriculture, for example, one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activators, molluscicides, and pheromones (chemical or biological). Mixing the compounds of the present invention or their compositions in a form useful as pesticides with other pesticides often results in a broader spectrum of pesticidal action. For example, the compounds of Formula I, I', I" or I'" of the present invention can be effectively combined or used in combination with pyrethroids, neonicotinoids, macrocyclic lactones, diamides, phosphates, carbamates, cycloalkadienes, formamidines, tin phenoxide compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pyrroles, and the like.

[0143] By adding, for example, one or more insecticides, acaricides, nematicides, and / or fungicides, the activity of the compositions according to the invention can be significantly broadened and adapted to prevailing environments. Combinations of compounds of formula I, I', I" or I'" with other insecticides, acaricides, nematicides, and / or fungicides can also offer further, unexpected advantages, which can also be described in a broader sense as synergistic activity. For example, plants can tolerate them better, their phytotoxicity can be reduced, pests or fungi can be controlled at different stages of their development, or their behavior can be improved during production (e.g., during grinding or mixing, during storage, or during use).

[0144] The following list of pesticides together with the compounds that can be used according to the invention is intended to illustrate the possible combinations by way of example.

[0145] The following combinations of compounds of formula I, I', I" or I'" with another active compound are preferred (the abbreviation "TX" means "each compound selected from Table 1, Table A of the present invention"):

[0146] An adjuvant selected from the group consisting of petroleum + TX,

[0147] A miticide, which is selected from the group consisting of the following substances: 1,1-bis(4-chlorophenyl)-2-ethoxyethanol+TX, 2,4-dichlorophenylbenzenesulfonate+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide+TX, 4-chlorophenylphenylsulfone+TX, abamectin+TX, acetoquinone+TX, acetofenapyr+TX, flumethrin+TX, aldicarb+TX, aldicarb+TX, α-cypermethrin+TX, cypermethrin+TX, sulfamethoxam+TX, aminothioate+TX, amitriptyline+TX, amitriptyline hydrogen oxalate+TX, amitraz+TX, cypermethrin+TX, arsenic trioxide+TX, AVI382+TX, AZ60541+TX, azinphos-m-tetrahydrofuran ... arsenic trioxide+TX, AVI382+TX, AZ60541+TX, azinphos-m-tetrahydrofuran+TX, arsenic trioxide+TX, arsenic trioxide+TX, arsenic trioxide ethyl)+TX, azobenzene+TX, azacyclotin+TX, azothoate+TX, benclorac+TX, benoxafos+TX, benzoximate+TX, benzyl benzoate+TX, bifenazate+TX, bifenthrin+TX, binachlor+TX, bromethrin+TX, bromocyclene+TX, bromophos+TX, ethyl bromophos+TX, bromopropylate+TX, buprofezin+TX, butanone carbendazim+TX, butanone sulfone carbendazim+TX, butanone carbendazim+TX, lime sulfur mixture (calcium polysulfide)+TX, campheechlor+TX, carbanolate+TX, carbaryl+TX, carbofuran+TX, carbothion+TX, CGA50'439+TX, chinomethionat+TX, chlorbenside+TX, chlordimeform+TX, chlordimeform hydrochloride+TX, chlorfenapyr+TX, chlorfenapyr+TX, chlorfenson+TX, chlorfensulphide+TX, chlorfenphos+TX, ethyl ester acaricide Chlorobenzilate + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chlorpyrifos + TX, methyl chlorpyrifos + TX, chlorthiophos + TX, cinerin I + TX, cinerin II + TX, cinerins + TX, clofentezine + TX, closantel + TX, coumaphos + TX, crotamiton + TX, crotoxyphos + TX, thiophene + TX,Cyanthoate + TX, Cyflumetofen [400882-07-7] + TX, Cyhalothrin + TX, Cypermethrin + TX, DCPM + TX, DDT + TX, Demephion + TX, Demephion-O + TX, Demephion-S + TX, Demeton + TX, Demeton-Methyl + TX, Demeton-O + TX, Demeton-Methyl-O + TX, Demeton-S + TX, Demeton-Methyl-S + TX, Demeton-S-methylsulphon + TX, Difenothiocarb + TX, Dialifos + TX, Dimethoate Azinphos + TX, dichlorvos + TX, dicliphos + TX, Kailesan + TX, dicrotophos + TX, pendimethalin + TX, dimefox + 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 rbon)+TX, dioxaphos+TX, diphenyl sulfone+TX, disulfiram+TX, ethophos+TX, DNOC+TX, dofenapyn+TX, doramectin+TX, endosulfan+TX, endothion+TX, EPN+TX, eprinomectin+TX, ethion+TX, ethoate-methyl+TX, etoxazole+TX, etrimfos+TX, fenazaflor+TX, quinazaquin+TX, fenbutatinoxide+TX, fenothiocarb+TX X, cypermethrin + TX, fenpyrad + TX, fenpyroximate + TX, fenson + TX, fentrifanil + TX, cypermethrin + TX, fipronil + TX, fluacrypyrim + TX, fluzolan + TX, flubenzimine + TX, flufenoxuron + TX, flucythrinate + TX, fluenetil + TX, flufenoxuron + TX, flumethrin + TX, fluorbenside + TX,flupyradifurone+TX, fluvalinate+TX, FMC1137+TX, fluvalinate+TX, fluvalinate hydrochloride+TX, formothion+TX, formparanate+TX, γ-HCH+TX, glyodin+TX, halfenprox+TX, heptenophos+TX, hexadecyl cyclopropanecarboxylate+TX, hexathiazolin+TX, iodomethane+TX, isocarbophos+TX, isopropyl O-(methoxyaminothiophosphoryl) salicylate+TX, ivermectin+TX 、jasmolin I+TX、jasmolin II+TX、jodfenphos+TX、lindane+TX、lufenlon+TX、malathion+TX、malonoben+TX、mecarbam+TX、mephosfolan+TX、methylthiophene+TX、methacrifos+TX、methamidophos+TX、methidathion+TX、methoate+TX、methodifosyl+TX、metolcarb+TX、metofenphos+TX、methyl bromide+TX、metolcarb+TX、metolcarb+TX、mexacarbate+TX、milbemycin+TX、milbemycin oxime)+TX, mipafox+TX, monocrotophos+TX, morphothion+TX, moxidectin+TX, naled+TX, NC-184+TX, NC-152+TX, nifluridide+TX, nikkomycin+TX, nitrilacarb+TX, nitrilacarb 1:1 zinc chloride complex+TX, NNI-0101+TX, NNI-0250+TX, oxydemeton-methyl (oxydemeton-methyl)+TX, oxamyl+TX, oxydeprofos+TX, sulfamethoxam ( oxydisulfoton)+TX, pp'-DDT+TX, parathion+TX, permethrin+TX, petroleum+TX, fenthion+TX, fenthion+TX, fenthion+TX, phorate+TX, phosalone+TX, phosfolan+TX, phosmet+TX, phosphamidon+TX, phoxim+TX, methyl pirimiphos+TX, polychloroterpenes+TX, polynactins+TX, prochlorperazine+TX, profenofos+TX, promacyl+TX, propargyl+TX, propetamphos+TX, propoxur+TX,Prothidathion + TX, prothoate + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins + TX, pyridaphenthion + TX, pyrimidifen + TX, pyrimidifen + 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, spiromesiclofen+TX, SSI-121+TX, sulfilam+TX, sulfluramid+TX, sulfotep+TX, sulfur+TX, S21-121 +TX, fluvalinate+TX, tebufenpyrad+TX, TEPP+TX, terbucarb+TX, stirofos+TX, tetradifon+TX, tetranactin+TX, tetrasul+TX, thiafenox+TX, thiocarboxime+TX, thiofanox+TX, thiometon-methyl )+TX, chlorpyrifos+TX, thuringiensin+TX, triamiphos+TX, triarathene+TX, triazophos+TX, triazuron+TX, trichlorfon+TX, trifenofos+TX, trinactin+TX, cypermethrin+TX, vaniliprole and YI-5302+TX,

[0148] An algaecide, the algaecide being selected from the group consisting of: 3-benzo[b]thiophen-2-yl-5,6-dihydro-1,4,2-oxathiazine-4-oxide+TX, copper dioctoate+TX, copper sulfate+TX, cybutryne+TX, dichlone+TX, dichlorophen+TX, endoxan+TX, fentin+TX, slaked lime+TX, nabam+TX, quinoclamine+TX, quinonamid+TX, simazine+TX, fentin acetate, and fentin hydroxide+TX.

[0149] An anthelmintic selected from the group consisting of abamectin + TX, clefonate + TX, doramectin + TX, emamectin + TX, emamectin benzoate + TX, eprinomectin + TX, ivermectin + TX, milbemycin + TX, moxidectin + TX, piperazine + TX, selamectin + TX, spinosad and thiophanate + TX,

[0150] An avicide selected from the group consisting of chloralose + TX, endrin + TX, fenthion + TX, pyridin-4-amine and strychnine + TX,

[0151] A bactericide, the bactericide consisting of a substance selected from the group consisting of 1-hydroxy-1H-pyridine-2-thione+TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide+TX, 8-hydroxyquinoline sulfate+TX, bronopol+TX, copper dioctanoate+TX, copper hydroxide+TX, cresol+TX, dichlorophen+TX, dispyrithione+TX, dodesine+TX, fenaminosulf+TX, formaldehyde+TX, mercurophen+TX, kasugamycin+TX, kasugamycin hydrochloride hydrate+TX, nickel bis(dimethyldithiocarbamate)+TX, nitrapyrin+TX, octhilinone+TX, oxolinic acid+TX, oxytetracycline+TX, potassium hydroxyquinoline sulfate+TX, probenazole+TX, streptomycin+TX, streptomycin sesquisulfate+TX, chlorpheniramine+TX, thiomersal+TX,

[0152] A biological agent, which is selected from the group consisting of the following substances: Adoxophyes orana GV+TX, Agrobacterium radiobacterium+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 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.tenebrionis+TX, 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 convergens)+TX, Leptomastix dactylopii parasitic wasp (Leptomastix dactylopii)+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae+TX, Neodiprion sertifer nuclear polyhedrosis virus and red-headed pine sawfly (Neodiprion sertifer) NPV+TX.lecontei nuclear polyhedrosis virus+TX, small flower stink bug+TX, Paecilomyces fumosoroseus+TX, Pasteuria penetrans+TX, Pasteuria thornei+TX, Pasteuria nishizawae+TX, Pasteuria ramosa+TX, Phytoseiulus persimilis+TX, Spodopteraexiguamulticapsid multinucleocapsid nuclear polyhedrosis virus+TX, Steinernema bibionis+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp.)+TX, Trichogramma+TX, Typhlodromus occidentalis, and Verticillium lecanii+TX.

[0153] A soil disinfectant selected from the group consisting of methyl iodide and methyl bromide + TX,

[0154] A chemical sterilant 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, trothamide and urethaneimide + TX,

[0155] An insect pheromone, the insect pheromone is selected from the group consisting of: (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol+TX, (E)-tridec-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)-eicos-13-en-10-one+TX, (Z) -Tetradec-7-en-1-al+TX, (Z)-tetradec-9-en-1-ol+TX, (Z)-tetradec-9-en-1-yl acetate+TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate+TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate+TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate+TX, 14-methyloctadec-1-ene+TX, 4-methylnonanal-5-ol and 4-methylnonanal-5-one+TX, α-multistriatin+TX, western pine beetle gathering pheromone (brevicomin)+TX, dodecadienoyl alcohol (codlelu re)+TX, codlemone+TX, cuelure+TX, disparlure+TX, dodec-8-en-1-yl acetate+TX, dodec-9-en-1-yl acetate+TX, dodec-8+TX, 10-dien-1-yl acetate+TX, dominicalure+TX, ethyl 4-methyloctanoate+TX, eugenol+TX, southern pine beetle gathering pheromone (frontalin)+TX, gossyplure+TX, grandlure+TX, grandlure mixture I+TX, grandlure mixture II+TX, Eugenol mixture III+TX, Eugenol mixture IV+TX, hexalure acetate+TX, ipsdienol+TX, ipsenol+TX, japonilure+TX, lineatin+TX, litlure+TX, looplure+TX, medlure+TX, megatomoicacid+TX, methyleugenol+TX, muscalure+TX, octadeca-2,13-dien-1-yl acetate+TX, octadeca-3,13-dien-1-yl acetate + TX, orfralure + TX, oryctalure + TX, ostramone + TX, siglure + TX, sordidin + TX, sulcatol + TX, tetradecene-11-yl acetate + TX, tert-butyl ketone + TX, tert-butyl ketone A + TX, tert-butyl ketone B1 + TX, tert-butyl ketone B2 + TX, tert-butyl ketone C and trunc-call + TX,

[0156] 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, ethyl hexanediol+TX, hexylurea+TX, methoquin-butyl+TX, methyl neodecylamide+TX, oxamate, and hydroxybenzoate+TX,

[0157] 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-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolane)methylcarbamate TX, 2-(4-chloro-3,5-xylyloxy)ethanol+TX, 2-chlorovinyl diethyl phosphate+TX, 2-imidazolidinone+TX, 2-isovalerylindan-1,3-dione+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate+TX, 2-thiocyanatoethyl laurate+TX, 3-bromo-1-chloroprop-1-ene+TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate+TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate+TX, avermectin+TX, acephate+TX, pyridinium chloride Amitraz + TX, domesticaphos + TX, acetofenapyr + TX, flumethrin + TX, acrylonitrile + TX, cotton boll carb + TX, aldicarb + TX, aldisulfone carb + TX, chlorfenapyr + TX, allethrin + TX, aloamicin + TX, cypermethrin + TX, α-cypermethrin + TX, α-ecdysone + TX, aluminum phosphide + TX, thiothion + TX, thioamide + TX, cypermethrin + TX, amimidone + TX, amimidone hydrogen oxalate + TX, amitraz + TX, neonicotinoid + TX, ethylmethidathion + TX, AVI382 + TX, AZ60541 + TX, azadirachtin + TX, methylpyriphos + TX, azinphos-methyl + TX, azinphos-methyl + TX, Bacillus thuringiensis Bacterial δ-endotoxins + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, cypermethrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, bendiocarb + TX, benfuracarb + TX, sulfanilamide + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bifenthrin + TX, bio-allethrin + TX, bio-allethrin S-cyclopentenyl isomer + TX, bioethanomethrin + TX, pyrethrin + TX, bis(2-chloroethyl) ether + TX, bistrifluan + TX, borax + TX, bromethrin + TX, bromophenirone + TX, bromo-DDT + TX,Bromophos + TX, bromophos-ethyl + TX, thiamethoxam + TX, buprofezin + TX, cypermethrin + TX, butathiofos + TX, butanone carbendazim + TX, butyl phosphonate + TX, butanone carbendazim + TX, butyl pyridaben + TX, cadusafos + TX, calcium arsenate + TX, calcium cyanide + TX, calcium polysulfide + TX, toxaphene + TX, chlormethoxam + TX, carbaryl + TX, carbofuran + TX, carbon disulfide + TX, carbon tetrachloride + TX, trithion + TX, butanone carbendazim + TX, cartap + TX, cartap hydrochloride + TX, sivaldin + TX, bornyl carbendazim + TX, chlordane + TX, chlorfenapyr + TX, chlordane + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chloroxyphos + TX, chlorfenapyr + TX, chlorfenapyr + TX, Chlorfenapyr + TX, chlormethinol + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorpyrifos + TX, chlorpyrifos-methyl + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr I + TX, chlorfenapyr II + TX, chlorfenapyr + TX, cis-resmethrin + TX, cis-resmethrin + TX, cypermethrin + TX, chlorfenapyr + TX, closantel + TX, thiamethoxam + TX, acetyl Copper arsenite + TX, copper arsenate + TX, copper oleate + TX, coumaphos + TX, cypermethrin + TX, crotamiton + TX, baclofos + TX, clofosinate + TX, cryolite + TX, CS708 + TX, benzonitrile + TX, fenitrothion + TX, cyfluthrin + TX, cypermethrin + TX, flucythrin + TX, cyhalothrin + TX, cypermethrin + TX, cypermethrin + TX, cyproconazole + TX, d-limonene + TX, d-tetramethrin + TX, DAEP +TX, dazomethan+TX, DDT+TX, decarbofuran+TX, deltamethrin+TX, tanafurphos+TX, tanafurphos-O+TX, tanafurphos-S+TX, entafurphos+TX, entafurphos-methyl+TX, entafurphos-O+TX, entafurphos-O-methyl+TX, entafurphos-S+TX, entafurphos-S-methyl+TX, entafurphos-S-methylsulfone+TX, diafuron+TX, chlorophos+TX, diamidophos+TX, diazinon+TX, isochlorophos+TX, chlorfenapyr+TX, dichlorvos +TX, dicliphos+TX, dicresyl+TX, dicrotophos+TX, dicynilide+TX, dieldrin+TX, diethyl 5-methylpyrazol-3-yl phosphate+TX, diflubenzuron+TX, dihydroxypropyltheophylline (dilor)+TX, tetrafluthrin+TX, methylfluthrin+TX, dimethoate+TX, dimethoate+TX, pyrethrin+TX, methylchlorfenapyr+TX, dimethoate+TX, chlorpyrifos+TX, dimethoate+TX, chlorpyrifos+TX, dimethoate-diclexine+TX, dimethoate-diclexine+TX, propanol+TX, pentotropol+TX,Danosid + TX, dinotefuran + TX, fenthiocarb + TX, vesiculophos + TX, dioxocarb + TX, dimethoate + TX, dithiophos + TX, benzothiocarb + TX, dithiophos + TX, DNOC + TX, doramectin + TX, DSP + TX, ecdysone + TX, EI1642 + TX, emamectin + TX, emamectin benzoate + TX, EMPC + TX, fenthrin + TX, endosulfan + TX, fenthiophos + TX, endrin + TX, EPBP + TX, EPN + TX, fenvalerate + TX, eprinomectin + TX, esfenvalerate + TX, etaphos + TX, ethiofencarb + TX, ethiophos + TX , ethiprole + TX, thiophanate-methyl + TX, ethoprophos + TX, ethyl formate + TX, ethyl-DDD + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, ethoprophos + TX, ethoprophos + TX, EXD + TX, sulfamethoxam + TX, fenamiphos + TX, anti-mite azole + TX, pyraclostrobin + TX, fenfluramine + TX, fenitrothion + TX, fenfencarb + TX, fenoxacrim + TX, fenoxycarb + TX, cypermethrin + TX, cypermethrin + TX, fenpyrad + TX, fenthion + TX, fenthion-ethyl + TX, fenvalerate + TX, fipronil + TX, Flunicrofen + TX, flubendiamide [272451-65-7] + TX, flucofuron + TX, flufenacet + TX, flucythrin + TX, flufluanid + TX, flufenacet + TX, flucythrin + TX, FMC1137 + TX, flufenophos + TX, flufenophos + TX, flufenophos hydrochloride + TX, anthiophos + TX, formparanate + TX, fenthiophos + TX, forsporafen + TX, thiabendazole + TX, fenthiophos + TX, furathiocarb + TX, pyrethroid + TX, γ-cyhalothrin + TX, γ-HCH + TX, biguanide salt + TX, biguanide acetate +TX, GY-81+TX, benzyl azomethine+TX, chlorfenapyr+TX, HCH+TX, HEOD+TX, Feibuda+TX, heptenophos+TX, cypermethrin+TX, hexaflumuron+TX, HHDN+TX, hydrazone+TX, hydrocyanic acid+TX, methoprene+TX, hyquincarb+TX, imidacloprid+TX, cypermethrin+TX, indoxacarb+TX, iodomethane+TX, IPSP+TX, chlorfenapyr+TX, carbofuran+TX, isocarbophos+TX, isothiocarb+TX, isoflurane+TX, isothioate+TX, transplanting spirit+TX, isoprocarb+TX, O-(methoxyaminothiophosphoryl) salicylic acid isopropyl ester+TX, rice blasting agent+TX, isosulfanthate+TX, oxazophos+TX,Ivermectin + TX, jasmectin I + TX, jasmectin II + TX, iodine + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, chlorpentyl + TX, methoprene + TX, λ-cyhalothrin + TX, lead arsenate + TX, lepidomectin + TX, parabromophos + TX, lindane + TX, lirimfos + TX, lufenuron + TX, thiathion + TX, m-isopropylphenyl methylcarbamate + TX, magnesium phosphide + TX, malathion + TX, tebuconazole + TX, phosphazolin + TX, tetramethylphos + TX, phosphazolin + TX, diamectin + TX, mercurous chloride + TX, mesulfenfos + TX, metaflumizone + TX X、Methamidophos+TX、Methamidophos Potassium+TX、Methamidophos Sodium+TX、Cyclohexanil+TX、Methamidophos+TX、Methanesulfonyl Fluoride+TX、Methiocarb+TX、Methoprex+TX、Methoprex+TX、Methoprex+TX、Methothrin+TX、Methoxychlor+TX、Methoxybenzoyl+TX、Methyl Bromide+TX、Methyl Isothiocyanate+TX、Methyl Chloroform+TX、Methylene Chloride+TX、Methiofluthrin+TX、Methiocarb ... Bromophos + TX, naphthalene + TX, NC-170 + TX, NC-184 + TX, nicotine + TX, nicotine sulfate + TX, fluazifop + TX, nitenpyram + TX, nitrilotriazole + TX, pentocyanamide + TX, pentocyanamide 1:1 zinc chloride complex + TX, NNI-0101 + TX, NNI-0250 + TX, nornicotine + TX, flubendiamide + TX, noviflumuron + TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-ylphosphonothioate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphonothioate + TX, O, O,O',O'-Tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, omethoate + TX, oxamyl + TX, sulfone-methyl + TX, isosulfoxon + TX, sulfone-methyl + TX, pp'-DDT + TX, p-dichlorobenzene + TX, parathion + TX, parathion-methyl + TX, chlorfenuron + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, permethrin + TX, petroleum oils + TX, PH60-38 + TX, fenthion + TX, phenothrin + TX, pyralid + TX, phorate + TX, phosalone + TX, thiophanate-methyl + TX,pirimetaphos+TX, pirimetaphos+TX, cypermethrin-ethyl+TX, cypermethrin-methyl+TX, polychlorodicyclopentadiene isomers+TX, polychloroterpenes+TX, potassium arsenite+TX, potassium thiocyanate+TX, propylthioate+TX, precocious phos I+TX, precocious phos II+TX, precocious phos III+TX, acetyl pyrimidophos+TX, profenofos+TX, profluthrin+TX, cypermethrin+TX, pyrimidazopyr+TX, fenflurphos+TX, propoxur+TX, propanil+TX, ethiazole+TX, prothiophos+TX, thiophos+TX, protrifenbute+TX, pymetrozine+TX, pyraclostrobin+TX, pyrazophos+TX, pyrazophos-pyrimidophos (p pyrafluprole) + TX, pyrethrin + TX, pyresmethrin + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins + TX, pyridaben + TX, pyridaflufen + TX, pyrimidin + TX, pyrimidin + TX, pyriproxyfen + TX, pyriproxyfen + TX, quassia extract + TX, quinalphos + TX, quinalphos-methyl + TX, quintiofos + TX, R-1492 + TX, rafoxanide + TX, resmethrin + TX, rotenone + TX, RU15525 + TX, RU25475 + TX, Niana (r Yania) + TX, ryanodine + TX, sabaveratrol + TX, octamethrin + TX, cadusafos + TX, selamectin + TX, SI-0009 + TX, SI-0205 + TX, SI-0404 + TX, SI-0405 + TX, flutosan + TX, SN72129 + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenol + TX, sodium selenate + TX, sodium thiocyanate + TX, threonylthion + TX, spinosad + TX, spiromesifen + TX, spirotetramat + TX, sulcofuron + TX, sulcofuron-sodium + TX, sulfluramid + TX, thiamethoxam + TX, sulfonyl fluoride + TX X, thiopromide + TX, tars + TX, τ-fluvalinate + TX, thiamethoxam + TX, TDE + TX, tebufenozide + TX, tebufenpyrad + TX, butylpyrimidophos + TX, tefluthrin + TX, tebufenox + TX, TEPP + TX, cypermethrin + TX, terbam + TX, terbufos + TX, tetrachloroethane + TX, cypermethrin + TX, θ-cypermethrin + TX, thiacloprid + TX, thiafenox + TX, thiamethoxam + TX, thicrofos + TX, cyfluthrin + TX, cyfluthrin hydrogen oxalate + TX, thiodicarb + TX, long-lasting carb + TX, methyl thiosulfate + TX, cyfluthrin + TX,Thiosultap+TX, thiosultap-sodium+TX, thuringin+TX, tolfenpyrad+TX, tralomethrin+TX, transfluthrin+TX, transpermethrin+TX, cypermethrin+TX, triazophos+TX, triazophos+TX, trichlorfon+TX, trichlormetaphos-3+TX, chlorpyrifos+TX, trichlorprop+TX, triflumuron+TX, thiocarb+TX, methoprene+TX, aphidoxime+TX, vaniliprole+TX, veratridine+TX, veratridine+TX, XMC+TX, methoprene+TX, YI-5302+TX, ζ-cypermethrin+TX, zetamethrin+TX, zinc phosphide+TX, zolaprofos, and ZXI8901+TX, cyantraniliprole[7369 94-63-19]+TX, chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinetoram [187166-40-1+1871 66-15-0]+TX, spirotetramat[203313-25-1]+TX, sulfoxaflor[946578-00-3]+TX, flufiprole[704886-18-0]+TX, chlorfenapyr[915288-13-0]+TX, tetramethylfluthrin[84937-88-2]+TX,

[0158] A molluscicide selected from the group consisting of di(tributyltin) oxide + TX, bromoacetamide + TX, calcium arsenate + TX, cloethocarb + TX, copper acetyl arsenite + TX, copper sulfate + TX, triphenyltin + TX, ferric phosphate + TX, metaldehyde + TX, methiocarb + TX, niclosamide + TX, niclosamide ethanolamine + TX, pentachlorophenol + TX, sodium pentachlorophenoxide + TX, tazimcarb + TX, thiodicarb + TX, tributyltin oxide + TX, trifenmorph + TX, trimethacarb + TX, triphenyltin acetate and triphenyltin hydroxide + TX, pyriprole + TX,

[0159] A nematicide, the nematicide is selected from the group consisting of the following substances: AKD-3088+TX, 1,2-dibromo-3-chloropropane+TX, 1,2-dichloropropane+TX, 1,2-dichloropropane and 1,3-dichloropropylene+TX, 1,3-dichloropropylene+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide+TX, 3-(4-chlorophenyl)-5-methylrhodanine+TX, 5-methyl-6-thio-1,3,5-Thiadiazin-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, avermectin + TX, acetofenapyr + TX, doxorubicin + TX, aldicarb + TX, aldoxycarb + TX, AZ60541 + TX, benclothiaz + TX, benclothiaz + TX, butylpyridaben + TX, cadusafos + TX, carbofuran + TX, carbon disulfide + TX, carbosulfan + TX, chloropicrin + TX, chlorpyrifos + TX, cloethocarb + TX, cytokinins + TX, dazomet + TX, DBCP + TX, DCIP + TX, diamidafos + TX, dichlofenthion + TX, dicliphos + TX, dimethoate +TX, imastatin +TX, imastatin benzoate +TX, eprinomectin +TX, eprinomectin +TX, ethoprophos +TX, ethylene dibromide +TX, fenamiphos +TX, tebufenpyrad +TX, fenpyrad +TX, fosthiazate +TX, fosthietan +TX, furfural +TX, GY-81 +TX, heterophos +TX, iodomethane +TX, isamidofos +TX, isazofos +TX, kinetin +TX, mecarphon +TX, mecarphon +TX, metamifene +TX, metamifene potassium +TX, metamifene sodium +TX, methyl bromide +TX, methyl isothiocyanate +TX, milbemycin oxime oxime) + TX, moxidectin + TX, Myrothecium verrucaria component + TX, NC-184 + TX, oxamyl + TX, phorate + TX, phosphamidon + 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,

[0160] A nitrification inhibitor selected from the group consisting of potassium ethylxanthate and nitrapyrin + TX,

[0161] A plant activator selected from the group consisting of acibenzolar+TX, acibenzolar-S-methyl+TX, probenazole, and Reynoutria sachalinensis extract+TX.

[0162] A rodenticide, the rodenticide is selected from the group consisting of: 2-isovaleryl indane-1,3-dione + TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, α-chlorohydrin + TX, aluminum phosphide + TX, antoxin + TX, arsenic trioxide + TX, barium carbonate + TX, bifenthionine + TX, brodifacoum + TX, brodifacoum + TX, calcium cyanide + TX, azotobactone + TX, chlorofacitin + TX, vitamin D3 + TX, chlorfenapyr ... Sodium thiazolin + TX, vitamin D2 + TX, fludioxaline + TX, fluoroacetamide + TX, thiazolin + TX, thiazolin hydrochloride + TX, β-HCH + TX, HCH + TX, hydrocyanic acid + TX, iodomethane + TX, lindane + TX, magnesium phosphide + TX, methyl bromide + TX, thiazolin + TX, phosphine + TX, phosphorus + TX, warfarin + TX, potassium arsenite + TX, warfarin + TX, scilla glycoside + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, thallium sulfate + TX, warfarin and zinc phosphide + TX,

[0163] A synergist selected from the group consisting of: 2-(2-butoxyethoxy)ethyl piperonyl ester+TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone+TX, farnesol with nerolidol+TX, MB-599+TX, MGK264+TX, piperonyl butoxide+TX, piprotal+TX, propylisomer+TX, S421+TX, sesamex+TX, sesasmolin and sulfoxide+TX,

[0164] 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, guazatine acetate + TX, methiocarb + TX, pyridin-4-amine + TX, salamine + TX, trimethacarb + TX, zinc naphthenate, and ziram + TX.

[0165] A virucide selected from the group consisting of imanin and ribavirin+TX,

[0166] A wound protective agent, which is selected from the group consisting of mercuric oxide + TX, octhilinone and methyl thiophanate + TX,

[0167] and a biologically active compound selected from the group consisting of: azaconazole (60207-31-0] + TX, triaconazole [70585-36-3] + TX, oxadiazol [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX, fluquinconazole [136426-54 -5]+TX, flusilazole[85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole[79983-71-4]+TX, imazalil[35554-44-0]+TX, imipenem[86598-92-7]+TX, piclonil[125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil[88671-89-0]+TX, pyraclostrobin[101903-30-4]+TX, penconazole[66246-88-6]+TX, Prothioconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, fluconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimefon [55219-65-3] + TX , triflumizole [99387-89-0] + TX, trichlorfonazole [131983-72-7] + TX, tricyclamide [12771-68-5] + TX, chlorfenapyr [60168-88-9] + TX, fluchlorfonamide [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, Dodecamorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamorph [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX, pyraclostrobin [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX,Flunix [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, benalaxyl [71626-11-4] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, furamide [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacar b) [62732-91-6] + TX, chloranil [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、Carboxin[5234-68-4]+TX、Furoxanilide[24691-80-3]+TX、Flutolanil[66332-96-5]+TX、Methiopyrad[55814-41-0]+TX、Oxycarboxin[5259-88-1]+TX、Penthiopyrad[183675-82-3]+TX、Thiopyrad[130000-40-7]+TX、Biguanide[108173-90-6]+TX、Dodine[2439-10-3][112-65-2](free bond)+ TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, etherstrobin [149961-52-4] + TX, enestrobin {Proc. BCPC, Int. Congr., Glasgow. 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX methyl etherstrobin [143390-89-0] + TX, oxazolidinone [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, trifloxystrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX,Pyraclostrobin [175013-18-0] + TX, ferbam [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, metiram [9006-42-2] + TX, propineb [12071-83-9] + TX, salamine [137-26-8] + TX, maneb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX, captan [133-06-2] + TX, difluanid [1085-98-9] + TX, oxazolidinone (f luoroimide) [41205-21-4] + TX, folpet [133-07-3] + TX, toluenesulfonamide [731-27-1] + TX, Bordeaux mixture [8011-63-0] + TX, copper hydroxide (copperhydroxid) [20427-59-2] + TX, copper chloride (copperoxychlorid) [1332-40-7] + TX, copper sulfate (coppersulfat) [7758-98-7] + TX, copper oxide (copperoxid) [1317-39-1] + TX, mancopper (mancopper) [539 88-93-5]+TX, oxine-copper[10380-28-6]+TX, dinocap[131-72-6]+TX, nitrothal-isopropyl[10552-74-6]+TX, kewensan[17109-49-8]+TX, iprobenphos[26087-47-8]+TX, isoprothiol[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, difop-butyl[101-05-3]+TX, benzthiazolin[413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat[2439-01-2]+TX, chloroneb[2675-77-6]+TX, chlorothalonil[1897-45-6]+TX,Cyflufenacil [180409-60-3] + TX, Cymoxanil [57966-95-7] ​​+ TX, Dichloronaphthoquinone [117-80-6] + TX, Diclocymet [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, famoxadone [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, fenhexamid [126833-17-8] +TX, fosetyl-aluminium [39148-24-8] +TX, hymexazol ol)[10004-44-1]+TX, propineb[140923-17-7]+TX, IKF-916(Cyazofamid)[120116-88-3]+TX, kasugamycin[6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, mefenacet[220899-03-6]+TX, pencycuron(p encycuron) [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] + TX,Pyroquilon [57369-32-1] + TX, quinoxyfen [124495-18-7] + TX, pentachloronitrobenzene [82-68-8] + TX, sulfur [7704-34-9] + TX, thiazolin [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, triamcinol [26644-46-2] + TX, validamycin [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-methano-naphthalen-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-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone + TX, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2 -[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone [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-thiophen-3-yl)-ethyl] + TX.

[0168] References in square brackets after the active ingredient, such as [3878-19-1], refer to Chemical Abstracts registration numbers. The mixing partners described above are known. For example, they are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13th Edition; Editor: CDS Tom Lin; The British Crop Protection Council] or in the "Compendium of Pesticide Common Names".

[0169] Most of the active ingredients mentioned above are referred to above by the so-called "common name", the related "ISO common name" or, in individual cases, another "common name". If the name is not a "common name", the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "traditional name", "compound name", or "development code" is used, or if neither one of these names nor the "common name" is used, an "alternative name" is used.

[0170] The mass ratio of any two ingredients in each combination is selected to give the desired, for example, synergistic effect. In general, the mass ratio will vary depending on the specific ingredients and how much of the ingredient is present in the combination. In general, the mass ratio between the two ingredients in any combination of the present invention is independently from one another from 100:1 to 1:100, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81:19, 80:2 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: 72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8:92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98 to 1:99. The preferred mass ratio between any two components of the present invention is from 75:1 to 1:75, more preferably 50:1 to 1.50, especially 25:1 to 1:25, advantageously 10:1 means 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, mass ratios and, on the other hand, molar ratios.

[0171] Examples of methods of application of the compounds and compositions of the present invention, i.e. methods of controlling pests / fungi in agriculture, are spraying, misting, dusting, brushing, seed dressing, broadcasting or pouring - which are selected to suit the intended purpose under the prevailing circumstances.

[0172] A preferred method of application in agriculture is application to the leaves of the plants (foliar application), it being possible to select the frequency and rate of application in accordance with the risk of infection by the pest / fungus in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action) by applying the compound to the locus of the plants, for example, by applying a liquid composition of the compound to the soil (by drench) or by applying the compound in solid form in the form of granules to the soil (soil application). In the case of rice plants, such granules can be metered into flooded paddies.

[0173] The application rates per hectare are generally 1 g to 2000 g of active ingredient per hectare, in particular 10 g / ha to 1000 g / ha, preferably 10 g / ha to 600 g / ha, such as 50 g / ha to 300 g / ha.

[0174] These compounds of the present invention and composition thereof are also suitable for the protection (for example seed, such as fruit, tuber or grain, or nursery plant) of plant propagation material against the harmful organism of above-mentioned type.This propagation material can be processed with this compound before planting, and for example seed can be processed before sowing.Alternately, this compound can be applied to seed grain (coating), and this is by being immersed in liquid composition by grain or by applying a kind of solid composition layer and realize.When this propagation material is planted in the application site, it is also possible for example to apply these compositions to seed furrow during drilling.These treatment methods for plant propagation material and the plant propagation material therefore processed are other themes of the present invention.Typically, treatment rate will depend on plant and harmful organism / fungus to be controlled, usually between 1 gram to 200 grams of every 100kg seeds, preferably between 5 grams to 150 grams of every 100kg seeds, as between 10 grams to 100 grams of every 100kg seeds.

[0175] The term seed includes all kinds of seeds and plant propagules including but not limited to true seeds, seed pieces, suckers, kernels, bulbs, fruits, tubers, grains, rhizomes, cuttings, cuttings and the like and in a preferred embodiment refers to true seeds.

[0176] The present invention also includes seeds coated or treated with a compound of formula I, I', I" or I'" or containing a compound of formula I. The term "coated with or treated with and / or containing" generally means that in most cases the active ingredient is on the surface of the seed when applied, although a greater or lesser 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 available a plant propagation material having adhered thereto a compound of formula I, I', I" or I'" . In addition, a composition comprising plant propagation material treated with a compound of formula I, I', I" or I'" is thereby obtainable.

[0177] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. Seed treatment application of a compound of Formula I, I', I" or I'" can be achieved by any known method, such as spraying or dusting the seeds before sowing or during sowing / planting.

[0178] Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, corn or sorghum; beets, such as sugar beets or fodder beets; fruit, such as pome, stone or stoneless fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, such as strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soybeans; oilseed plants, such as rapeseed, mustard, chestnuts, olives, sunflowers, coconuts, castor beans, cocoa or peanuts; cucurbit crops, such as pumpkins, cucumbers or melons; Fiber plants, such as cotton, flax, hemp, or jute; citrus fruits, such as oranges, lemons, grapevines, or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers; plants of the Lauraceae family, such as avocado, Cinnamonium, or camphor; and also tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevines, hops, plantaginaceae, rubber plants, and ornamental plants (e.g., flowers and lawn plants or turf).

[0179] In one embodiment, the plant is selected from the group consisting of cereals, corn, soybeans, rice, sugarcane, vegetables, and oil plants.

[0180] The term "plants" is to be understood as also including plants transformed by the use of recombinant DNA techniques and which are able to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular Bacillus.

[0181] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus subtilis or Bacillus japonicus; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), such as Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of nematode symbiotic bacteria, such as Photorhabdus or Xenorhabdus, such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, spider toxins, wasp toxins, and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomyces toxins; plant Lectins, such as pea lectin, barley lectin or snowdrop lectin; lectins; protease inhibitors, such as trypsin inhibitor, serine protease inhibitor, potato storage protein (patatin), cysteine ​​protease inhibitor, papain inhibitor; ribosome inactivating protein (RIP), such as ricin, corn-RIP, abrin, luffa seed toxin, saporin or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitor, HMG-COA-reductase, ion channel blockers, such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0182] In the context of the present invention, δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vips), such as Vip1, Vip2, Vip3 or Vip3A, should be understood to include, obviously, mixed toxins, truncated toxins and modified toxins. Mixed toxins are produced by recombinantly combining different regions of those proteins (see, for example, WO02 / 15701). Truncated toxins such as truncated Cry1Ab are known. In the case of modified toxins, one or more amino acids of a naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that a non-naturally occurring protease recognition sequence be inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO03 / 018810).

[0183] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0374753, WO 93 / 07278, WO 95 / 34656, EP-A-0427529, EP-A-451878 and WO 03 / 052073.

[0184] Methods for preparing such transgenic plants are known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0367474, EP-A-0401979 and WO 90 / 13651.

[0185] The toxins contained in the transgenic plants render the plants tolerant to harmful insects. Such insects may be found in any insect taxonomic group, but are particularly commonly found in beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0186] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some are commercially available.

[0187] Typically, the compounds of the invention are used in the form of a composition (eg, a formulation) comprising a carrier. The compounds of the present invention and their compositions can be used in different forms, for example, aerosol sprayers, capsule suspensions, cold atomization concentrates, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, capsule granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-generating products, granules, hot atomization concentrates, macrogranules, 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 suspensions (ulv), 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.

[0188] A formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation adjuvants, which may be solid or liquid adjuvants, 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, binders, and / or tackifiers. The composition may further comprise a fertilizer, micronutrient donor, or other product that influences plant growth, and includes a combination comprising a compound of the invention and one or more other bioactive agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

[0189] The present invention therefore also makes available a composition comprising a compound according to the invention together with an agronomically suitable carrier and optionally one or more customary formulation auxiliaries.

[0190] These compositions are prepared with methods known per se, for example by grinding, screening and / or squeezing solid compounds of the present invention and in the presence of at least one auxiliary agent, for example by closely mixing and / or grinding the compound of the present invention with one or more auxiliary agents. In the case of solid compounds of the present invention, the grinding / grinding of the compound is in order to ensure a specific particle size. The methods for preparing these compositions and the purposes of these compounds of the present invention for preparing these compositions are also a theme of the present invention.

[0191] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in a polymeric mass, these compositions comprising at least one compound according to the invention and the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0192] Examples of suitable liquid carriers are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably C8 to C 12 alkylbenzene moieties, such as xylene mixtures, alkylated naphthalenes or tetralins, 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-methylpyrrolidin-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, non-epoxidized or epoxidized vegetable oils, such as non-epoxidized or epoxidized rapeseed oil, castor oil, coconut oil or soybean oil, and silicone oils.

[0193] Examples of solid carriers for example dusts and dispersible powders are ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite normally. In order to improve physical properties, it is also possible to add highly dispersed silica or highly dispersed absorbent polymers. Suitable particle adsorptive carriers for granules are porous, such as pumice, gravel, sepiolite or bentonite, and suitable non-absorptive carrier materials are calcite or sand. In addition, a large amount of granulated materials of inorganic or organic natural materials can be used, particularly dolomite or pulverized plant residues.

[0194] Depending on the type of active ingredient to be formulated, suitable surface-active compounds are nonionic, cationic and / or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties. The surfactants mentioned below are to be regarded only as examples; a large number of other surfactants conventionally used in the field of formulations and suitable according to the present invention are described in the relevant literature.

[0195] Suitable nonionic surfactants are, in particular, polyethylene glycol ether derivatives of aliphatic or cycloaliphatic alcohols, polyethylene glycol ether derivatives of saturated or unsaturated fatty acids or polyethylene glycol ether derivatives of alkylphenols, which may contain from about 3 to about 30 glycol ether groups and from about 8 to about 20 carbon atoms in the (cyclo)aliphatic hydrocarbon residue or from about 6 to about 18 carbon atoms in the alkyl portion of the alkylphenol. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol or alkylpolypropylene glycols having from 1 to about 10 carbon atoms in the alkyl chain and from about 20 to about 250 glycol ether groups and from about 10 to about 100 propylene glycol ether groups. Typically, the above compounds contain from 1 to about 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonoxynol, castor oil polyethylene glycol ether, polypropylene glycol / polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

[0196] These cationic surfactants are in particular quaternary ammonium salts which generally have at least one alkyl residue (from about 8 to about 22 carbon atoms) as a substituent and (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl residues as further substituents. These salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.

[0197] Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds. Examples of suitable soaps are alkali metal salts, alkaline earth metal salts, or (unsubstituted or substituted) ammonium salts of fatty acids having from about 10 to about 22 carbon atoms, such as the sodium or potassium salts of oleic acid or stearic acid, or natural fatty acid mixtures (obtainable, for example, from coconut oil or tall oil); mention should also be made of the fatty acid methyltaurine. However, synthetic surfactants are more commonly used, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives, or alkylarylsulfonates. These fatty sulfonates and fatty sulfates are usually alkali metal salts, alkaline earth metal salts, or (substituted or unsubstituted) ammonium salts and usually have alkyl residues having from about 8 to about 22 carbon atoms, alkyl also being understood as an alkyl moiety including acyl residues; examples that may be mentioned are the sodium or calcium salts of ligninsulfonic acid, the sodium or calcium salts of lauryl sulfate, or the sodium or calcium salts of fatty alcohol sulfate mixtures prepared from natural fatty acids. This group also includes sulfates and sulfonates 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 alkylarylsulfonates are sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid / formaldehyde condensates. In addition, suitable phosphates, such as the phosphate esters of p-nonylphenol / (4-14)ethylene oxide adducts, or phospholipids are also possible.

[0198] Typically, these compositions comprise from 0.1% to 99% (in particular from 0.1% to 95%) of a compound according to the invention and from 1% to 99.9% (in particular from 5% to 99.9%) of at least one solid or liquid carrier, it being possible in principle for 0% to 25% (in particular from 0.1% to 20%) of the composition to be a surfactant (in each case % denotes percentage by weight). However, for commercial purposes, concentrated compositions are generally preferred, the end user in principle using diluted compositions having a significantly lower concentration of active ingredient.

[0199] Examples of suitable formulation types for tank mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0200] As to the nature of the formulations, the methods according to the invention, such as foliage, drench, spraying, atomizing, dusting, spreading, coating or pouring, may be chosen according to the intended purposes and the prevailing circumstances.

[0201] Such tank-mix compositions are generally prepared by diluting one or more pre-mix compositions containing different pesticides and, optionally, additional adjuvants with a solvent (eg, water).

[0202] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, extenders, binders or fertilizers.

[0203] Generally, tank-mix formulations for foliar or soil application comprise 0.1% to 20%, especially 0.1% to 15%, of the desired ingredients and 99.9% to 80%, especially 99.9% to 85%, of solid or liquid adjuvants (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 20%, especially 0.1% to 15%, based on the tank-mix formulation.

[0204] Typically, premix formulations for foliar application comprise 0.1% to 99.9%, in particular 1% to 95%, of the desired ingredient and 99.9% to 0.1%, in particular 99% to 5%, of solid or liquid adjuvants (including, for example, a solvent such as water), whereby the adjuvants may be a surfactant, in an amount of 0 to 50%, in particular 0.5% to 40%, based on the premix formulation.

[0205] Typically, tank mix formulations for seed treatment applications comprise 0.25 to 80%, especially 1 to 75%, of the desired ingredients, and 99.75 to 20%, especially 99 to 25%, of solid or liquid adjuvants (including, for example, a solvent such as water), where the adjuvant can be a surfactant in an amount of 0 to 40%, especially 0.5 to 30%, based on the tank mix formulation.

[0206] Typically, premix formulations for seed treatment applications comprise 0.5% to 99.9%, especially 1% to 95% of the desired ingredients, and 99.5% to 0.1%, especially 99% to 5%, of solid or liquid adjuvants (including, for example, a solvent such as water), where the adjuvants can be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the tank mix formulation.

[0207] While commercial products are preferably formulated as concentrates (eg, pre-mix compositions (formulations)), end users typically employ diluted formulations (eg, tank mix compositions).

[0208] Preferred seed treatment premix formulations are aqueous suspension concentrates. This formulation can be applied to the seed using conventional processing techniques and machines, such as fluidized bed technology, drum grinding method, static rotation (rotostatic) seed processor and drum applicator. Other methods, such as spouted bed, can also be useful. These seeds can be pre-coated with glue before coating. After coating, these seeds are typically dried and then transferred to a glue coating machine for coating. Such methods are well known in the art.

[0209] Generally, the premix composition of the invention comprises 0.5 to 99.9% by mass, in particular 1 to 95%, advantageously 1 to 50% by mass of the desired ingredients, and 99.5 to 0.1%, in particular 99 to 5% by mass of solid or liquid adjuvants (including, for example, a solvent such as water), wherein the auxiliary agents (or adjuvants) may be a surfactant in an amount of 0 to 50%, in particular 0.5 to 40%, by mass, based on the premix formulation.

[0210] In a preferred embodiment, independent of any other embodiment, the compound of formula I, I', I" or 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. The composition or mixture for protecting plant propagation material may also comprise at least one copolymer from water-soluble and water-dispersible film-forming polymers that improve the attachment of the active ingredient to the treated plant propagation material, the polymers generally having an average molecular weight of at least 10,000 to about 100,000.

[0211] The combinations of the invention (ie, those comprising a compound of the invention and one or more additional biologically active agents) may be administered simultaneously or sequentially.

[0212] In this case, the components of a combination are administered sequentially (i.e., one by one), and these components are administered sequentially within a reasonable period of time to achieve the biological effect, such as within a few hours or days. The order of administration of the components of the combination, i.e., whether the compound of formula I, I', I" or I'" should be administered first, is not critical for practicing the present invention.

[0213] In the case where the ingredients of the combination are applied simultaneously in the present invention, they may be applied as a composition comprising the combination, in which case (A) the compound of formula I, I', I" or I'" and one or more ingredients of the combination may be obtained from a separate formulation source and mixed together (referred to as a tank mix, ready-to-use, spray broth or slurry), or (B) the compound of formula I, I', I" or I'" and one or more ingredients of the combination may be sourced as a separate formulation mixture (referred to as a premix, i.e., mixture, concentrate or formulated product).

[0214] In one embodiment, independently of other embodiments, a compound according to the invention is administered as a combination. Thus, the present 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 tank mix or premix composition.

[0215] As an alternative to actual synergistic effects with biological activity, the combinations according to the invention may have unexpectedly advantageous properties which may be desirable as synergistic activities in a broader sense. Examples of such advantageous properties which 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.

[0216] The compounds of the invention are preferably used as a nematicide in agriculture.

[0217] The compounds of the present invention may also find application in other areas, such as one or more of the following: protection of stored goods and storage rooms, protection of raw materials (such as wood panels, textiles), floor coverings and buildings, and in hygiene management - especially protection of humans, livestock, and productive livestock against harmful organisms. The present invention thus also makes available pesticidal compositions and methods for such uses. Such compositions for specific uses will need to be modified, and one of ordinary skill will be able to make such compositions available for any specific use.

[0218] In the hygiene field, the compositions according to the invention are effective against ectoparasites such as hard ticks, soft ticks, scabies, autumn mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

[0219] The compositions according to the invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and buildings from insect attack. The compositions according to the invention can be used, for example, to combat the following pests: beetles, such as the American house beetle, the hairy green tiger beetle, the furniture beetle, the death beetle, Ptilinuspecticornis, Dendrobium pertinex, the fine-toothed fork-tailed beetle, Priobium carpini, the brown powder beetle, the African powder beetle, the southern powder beetle, the flat-stomached beetle, the soft-haired powder beetle, the flat-legged powder beetle, the scale-haired powder beetle, the wood beetle, the wood beetle, the black beetle, the red-bellied oak beetle, the brown heteroptera beetle, the two-spined beetle and the bamboo beetle, and also members of the Hymenoptera, such as the blue-black wood beetle, the giant wood beetle, the Taiga wood beetle and Urocerus augu, and termites such as the yellow-necked wood termite, the hemp-headed sand-mound termite, the Indian and Pakistani structural wood termite, the yellow-limbed Reticulitermes, the Sant's Reticulitermes, the European Reticulitermes, the Das-like termite, the Nevadan termite and the Formosan termite, as well as wingless insects such as silverfish.

[0220] Methods for applying a compound or a combination thereof to stored goods, storage rooms, raw materials (such as wood panels and textiles), floor coverings and buildings, and in hygiene management are known in the art.

[0221] The present invention also provides a method for treating, controlling, preventing and protecting warm-blooded animals (including humans and fish) against infestations and infections caused by helminths, arachnids and arthropod endo- and ectoparasites, which method comprises administering or applying orally, topically or parenterally to the animal an anthelmintic, acaricidal or endo- or ectoparasiticidal amount of a compound of formula I, I', I" or I'".

[0222] The above method is particularly useful for controlling and preventing infestations and infections caused by helminths, nematodes, mites and endo- and ectoparasites in warm-blooded animals such as cattle, sheep, pigs, camels, deer, horses, poultry, fish, rabbits, goats, mink, fox, chinchillas, dogs and cats, as well as humans.

[0223] In the context of controlling and preventing infestations and infections in warm-blooded animals, the compounds of the present invention are particularly useful for controlling helminths and nematodes. Examples of helminths are members of the class Trematoda, commonly referred to as flukes or flatworms, particularly members of the genera Fasciola, Pseudomonas, Homochaetes, Diplochaetes, Ophisthorchis, Fasciola, Echinostoma, and Paragonimus. Nematodes that can be controlled by compounds of formula I, I', I" or I"' include Haemonchus, Osterleghorn, Cooperia, Oesphagastomu, Nematode, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaris, and the like.

[0224] The compounds of the present invention can also control infestations of endoparasitic arthropods, such as the larvae of the skin flies and the gastropod bots. In addition, ectoparasitic infestations of mites and arthropods in warm-blooded animals and fish, including biting lice, sucking lice, botflies, biting flies, muscoid flies, flies, myiasitic fly larvae, gnats, mosquitoes, fleas, mites, ticks, nasal bots, sheep bots, and chiggers, can be controlled, prevented, or eliminated by the compounds of the present invention. Biting lice include members of the order Trichophagus, such as the bovine hair louse, the dog hair louse, and the sheep wool louse (Damilina ovis). Sucking lice include members of the order Pediculus, such as the bovine blood louse, the suicidal blood louse, the bovine jaw louse, and the buffalo blind louse. Biting flies include members of the genus Nigrocera. Ticks include the genera Boophilus, Rhipicephalus, Ixodes, Hyalomma, Amblyomma, and Cercocephalus. The compounds of the present invention may also be used to control mites that are parasitic on warm-blooded mammals and poultry, including mites of the orders Acari and Parasiticus.

[0225] For oral administration to warm-blooded animals, the compounds of the present invention can be formulated into animal feed, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drench medications for animals, gels, tablets, boluses, and capsules. In addition, the compounds of the present invention can also be administered to animals in their drinking water. For oral administration, the selected dosage form should provide the animals with approximately 0.01 mg / kg to 100 g / kg of the compound of the present invention per day.

[0226] Alternatively, the compounds of the present invention can be administered parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection to animals. The compounds of the present invention can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention can be formulated as an implant for subcutaneous administration. In addition, the compounds of the present invention can be administered percutaneously to animals. For parenteral administration, the selected dosage form should provide the animals with a compound of the present invention at a dose of approximately 0.01 mg / kg to 100 mg / kg of animal body weight per day.

[0227] The compounds of the present invention can also be applied topically to the 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. In addition, the compounds of the present invention can be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

[0228] The compounds of the present invention may also be combined or used in conjunction with one or more other parasiticidal compounds (thereby broadening the spectrum of activity), including, but not limited to, anthelmintics such as benzimidazoles, piperazines, levamisole, thiophene pyrimidines, praziquantel, and the like; endectocides such as avermectins, milbemycins, and the like; ectoparasiticides such as arylpyrroles, organophosphates, carbamates, gamma-butyric acid inhibitors including fipronil, pyrethroids, spinosad, imidacloprid, and the like; insect growth regulators such as pyriproxyfen, cypromazine, and the like; and chitin synthase inhibitors such as benzoyl ureas including flufenoxuron.

[0229] The parasiticidal compositions of the present invention comprise a parasiticidally effective amount of a compound of the present invention or a combination thereof in admixture with one or more physiologically acceptable inert solid or liquid carriers known in veterinary practice for oral, transdermal, and topical administration. Such compositions may further include various additives, such as stabilizers, defoamers, viscosity regulators, binders, and tackifiers, and while commercial products will preferably be formulated as concentrates, the end user will generally use diluted formulations.

[0230] The compositions according to the invention can also be used for the preparation of compositions for the therapeutic or preventive treatment of fungal diseases in humans and animals, such as, for example, mycoses, dermatoses, tinea versicolor and candidiasis or diseases caused by Aspergillus species, such as Aspergillus fumigatus.

[0231] In one embodiment, independent of any other embodiment, the compound of formula I, I', I", or I'" is an anthelmintic compound.

[0232] In one embodiment, independent of any other embodiment, the compound of formula I, I', I" or I'" is a pesticidal compound, preferably a nematicidal compound. DETAILED DESCRIPTION

[0233] The following examples are provided to illustrate the present invention and should not be considered to limit the present invention in any way. The scope of the rights claimed in the present invention is described in the claims.

[0234] Given the economical efficiency and diversity of the compounds, we have selected and synthesized a number of compounds. A selection of these compounds is listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are intended to better illustrate the present invention but are not intended to limit the present invention. Those skilled in the art should not interpret this as limiting the scope of the present invention to the following compounds.

[0235] Table 1 Compound structures and their 1 H NMR values

[0236] Table A is constructed in the same manner as Table 1 above, except that the general formula I is replaced with a cis structure, such as general formula I'

[0237] In Table A, the entries under the "Serial Number" column heading are sequentially recited as 1 (cis) to 139 (cis). For example, 1 (cis) corresponds to the compound in Table 1 where Compound 1 is a cis form.

[0238] Table B is constructed in the same manner as Table 1 above, except that the compound having the general formula I is replaced with the compound having the general formula I having a chiral center.

[0239] In Table B, the entries under the "Serial Number" column heading are sequentially recited as 1(RR) to 139(RR). For example, 1(RR) corresponds to compound 1 in Table 1 in which both positions 1 and 2 on the four-membered ring are in R configuration.

[0240] Table C is constructed in the same manner as Table 1 above, except that the general formula I is replaced with the general formula I having a chiral center.

[0241] In Table C, the entries under the "Serial Number" column heading are sequentially recited as 1(SS) to 139(SS). For example, 1(SS) corresponds to compound 1 in Table 1 in which both positions 1 and 2 on the four-membered ring are in S configuration.

[0242] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The starting materials can be purchased commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions, and these modifications or variations of the preparation methods of the present invention that result in various isomerizations of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0243] The following process examples are provided to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthesis of the compounds shown in the table below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0244] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0245] 1. Synthesis of Compound 1

[0246] (1) Compound 1-1 (15 g, 1 eq) was dissolved in 150 mL of tetrahydrofuran, and 2-methyl-2-propanesulfenamide (8.4 g, 1.2 eq) and titanium tetraethoxide (26.5 g, 2 eq) were added in sequence. The mixture was heated to 70 ° C. and stirred for 5 h. After the reaction was completed, water was added to quench the reaction. The insoluble matter was filtered off with celite. The filtrate was extracted with water and ethyl acetate three times. The organic phases were combined, dried, concentrated, and mixed. The mixture was purified by normal phase purification to obtain compound 1-2 (17 g, 82%).

[0247] (2) Compound 1-2 (17 g, 1 eq) was dissolved in 200 mL of methanol. Sodium borohydride (3.55 g, 2 eq) was added in batches under ice bath conditions. The mixture was stirred in an ice bath for 1 h. The reaction was completed in the middle control period. The solvent was removed by concentration, and the mixture was extracted with water and ethyl acetate three times. The organic phases were combined, dried, and concentrated to obtain compound 1-3 (16 g, 94%).

[0248] (3) Compound 1-3 (200 mg, 1 eq) was dissolved in 10 mL of solvent (dioxane: water = 10:1), and phenylboric acid (80 mg, 1.2 eq), potassium carbonate (228 g, 3 eq), and 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (II) dichloromethane complex (22 mg, 0.05 eq) were added in sequence. The mixture was protected by nitrogen and heated to 100 ° C. Stirred overnight. The reaction was completed in the middle control. The mixture was extracted with water and ethyl acetate three times. The organic phases were combined, dried, concentrated, and mixed, and purified by normal phase to obtain compound 1-4 (90 mg, 45%).

[0249] (4) Compound 1-4 (90 mg, 1 eq) was dissolved in 10 mL of hydrochloric acid in ethyl acetate and stirred at room temperature for 30 min. After the reaction was completed, the mixture was directly concentrated and the oil pump was used to obtain the crude hydrochloride of compound 1-5 (90 mg).

[0250] (5) Compound 1-5 (90 mg, 1 eq) was dissolved in 20 mL of dichloromethane. 3-Bromopyridine-2-carboxylic acid (66 mg, 1 eq), triethylamine (106 mg, 3 eq), and HATU (200 mg, 1.5 eq) were added in sequence under ice bath conditions. The mixture was stirred at room temperature for 1-2 h. After the reaction was completed, the mixture was extracted with water and dichloromethane. The organic phase was washed three times with dilute hydrochloric acid, dried, concentrated, and purified by normal phase purification to obtain 1 (75 mg, 72%).

[0251] 2. Synthesis of compound 2 (cis)

[0252] 2-1 (200 mg, 1 eq) was dissolved in a mixed solvent (1,4-dioxane:water = 10:1), followed by the addition of 2-2 (77.8 mg, 1.2 eq), anhydrous potassium carbonate (190.4 mg, 3 eq), and a catalyst (CAS No. 95464-05-4, 7.6 mg, 0.02 eq). The reaction mixture was placed under nitrogen at 100°C overnight, and the reaction was completed by mid-control. The reaction mixture was concentrated and mixed, and then purified by normal phase purification to obtain product 2 (cis) (48 mg, 23%).

[0253] 3. Synthesis of Compound 3

[0254] (1) 1-3 (0.2 g, 1 eq) was dissolved in a mixed solution of 20 mL of dioxane and 1 mL of water at room temperature, and then p-fluorophenylboric acid (1.2 eq), cesium fluoride (3 eq) and Pd(dppf)Cl2 (0.03 eq) were added in sequence. After the addition was completed, nitrogen was protected, and the temperature was raised to 100°C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature, the insoluble matter was filtered off with celite, and the filtrate was concentrated and purified by normal phase to obtain 3-1 (180 mg, 86%).

[0255] (2) 3-1 (0.38 g, 1 eq) was dissolved in a small amount of dioxane, and then hydrochloric acid ethyl acetate solution was added. The mixture was stirred at room temperature for 1 hour. The reaction was completed in the intermediate control and concentrated to obtain 3-2 (0.12 g, 92%).

[0256] (3) 3-2 (120 mg, 1 eq) was dissolved in 10 ml of DCM, and then 3-bromo-2-pyridinecarboxylic acid (1.1 eq) and triethylamine (2 eq) were added in sequence, stirred at room temperature for 5 min, and finally HATU (1.5 eq) was added, and the reaction was stirred at room temperature for 3 h. After the mid-control reaction was completed, water was directly added to the system for extraction. The aqueous phase was extracted twice with DCM, and the organic phases were mixed. The organic phase was washed twice with dilute hydrochloric acid and once with saturated sodium chloride solution. The organic normal phase was concentrated and purified to obtain 3 (40 mg, 20%).

[0257] 4. Synthesis of Compound 106 (cis)

[0258] (1) 1-3 (16 g, 1 eq) was dissolved in a mixed solution of 200 mL of dioxane and 15 mL of water at room temperature, and then p-trifluoromethylphenylboronic acid (1.2 eq), cesium fluoride (3 eq) and Pd(dppf)Cl2 (0.03 eq) were added in sequence. After the addition was completed, nitrogen was protected, and the temperature was raised to 100°C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature, the insoluble matter was filtered off with celite, and the filtrate was concentrated and purified by normal phase to obtain 106-1 (6 g, 30%).

[0259] (2) 106-1 (6 g, 1 eq) was dissolved in 30 mL of dioxane, and then hydrochloric acid and ethyl acetate solution were added. The mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction was concentrated to obtain 106-2 (4.2 g, 92%).

[0260] (3) 106-2 (4.2 g, 1 eq) was dissolved in 100 mL of a mixed solvent (acetone: water = 3:1), and Fmoc-OSu (1 eq) and sodium bicarbonate (1.1 eq) were added sequentially under ice bath. The mixture was warmed to room temperature and stirred overnight. The reaction was completed by mid-control. The acetone was removed by concentration, and the mixture was extracted with water and ethyl acetate three times. The organic phases were combined, dried, concentrated, and mixed. The mixture was purified by normal phase purification. The peak with high polarity was selected and concentrated to obtain 106-3 (1.1 g, 14%).

[0261] (4) 106-3 (1.1 g, 1 eq) was dissolved in 30 mL of a 20% piperidine solution in DMF and stirred at room temperature for 1 to 2 hours. After the reaction was completed, the mixture was extracted with water and EA three times. The organic phases were combined and washed three times with saturated brine. The organic phases were concentrated to give 106-4 (600 mg, crude product).

[0262] (5) 106-4 (80 mg, 1 eq) was dissolved in 10 ml of DCM, and then 3-bromo-2-pyridinecarboxylic acid (1.1 eq) and triethylamine (2 eq) were added in sequence. The mixture was stirred at room temperature for 5 min. Finally, HATU (1.5 eq) was added and the mixture was stirred at room temperature for 3 h. After the intermediate control reaction was completed, water was directly added to the system for extraction. The aqueous phase was extracted twice with DCM. The organic phases were mixed and washed twice with dilute hydrochloric acid and once with saturated sodium chloride solution. The organic phase was concentrated and purified to obtain 106 (cis) (40 mg, 32%).

[0263] 5. Synthesis of Compounds 106(SS) and 106(RR)

[0264] (1) 106-4 (0.3 g, 1 eq) was dissolved in EA / PE mixed solvent, S-mandelic acid (0.5 eq) was added at room temperature and stirred for 30 min. Solids were slowly precipitated under stirring in an ice bath and filtered. The solids (chiral front peak) and mother liquor (chiral back peak) were washed with alkali respectively to obtain two configuration products, chiral front peak 106-6 (80 mg, 26%) and chiral back peak 106-7 (100 mg, 26%).

[0265] (2) 106-6 (80 mg, 1 eq) was dissolved in 10 ml of DCM, and then 3-bromo-2-pyridinecarboxylic acid (1.1 eq) and triethylamine (2 eq) were added in sequence, and stirred at room temperature for 5 min. Finally, HATU (1.5 eq) was added, and the reaction was stirred at room temperature for 3 h. After the mid-control reaction was completed, water was directly added to the system for extraction. The aqueous phase was extracted twice with DCM, and the organic phases were mixed. The organic phases were washed twice with dilute hydrochloric acid and once with saturated sodium chloride solution. The organic normal phase was concentrated and purified to obtain 106(SS) (70 mg, 56%).

[0266] (3) 106-7 (100 mg, 1 eq) was dissolved in 10 ml of DCM, and then 3-bromo-2-pyridinecarboxylic acid (1.1 eq) and triethylamine (2 eq) were added in sequence, and stirred at room temperature for 5 min. Finally, HATU (1.5 eq) was added, and the reaction was stirred at room temperature for 3 h. After the mid-control reaction was completed, water was directly added to the system for extraction. The aqueous phase was extracted twice with DCM, and the organic phases were mixed. The organic phases were washed twice with dilute hydrochloric acid and once with saturated sodium chloride solution. The organic normal phase was concentrated and purified to obtain 106 (RR) (78 mg, 54%).

[0267] 6. Synthesis of Compound 122

[0268] (1) 1-3 (200 mg, 1 eq), pinacol diboronate (213 mg, 1.5 eq), and potassium acetate (107 mg, 2 eq) were dissolved in 40 mL of dioxane solution at room temperature. Under nitrogen protection, [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (12 mg, 0.03 eq) was added. After the addition was complete, the temperature was raised to 100°C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature, and the filtrate was concentrated and purified by normal phase to obtain 122-1 (200 mg, 88%).

[0269] (2) 122-1 (200 mg, 1 eq), intermediate halide (128 mg, 1 eq), and cesium fluoride (199 mg, 3 eq) were dissolved in a mixed solution of 20 mL of dioxane and 2 mL of water at room temperature. Under nitrogen protection, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (10 mg, 0.03 eq) was added. After the addition was complete, the temperature was raised to 100 ° C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature, and the filtrate was concentrated and purified by normal phase to obtain 122-2 (200 mg, 88%).

[0270] (3) 122-2 (200 mg, 1 eq) was dissolved in 20 mL of Dioxane at room temperature, and then added to HCl / Dioxane solution at room temperature. The reaction was allowed to proceed at room temperature for 1 h. After the intermediate control reaction was completed, the filtrate was concentrated and purified by normal phase to obtain 122-3 (100 mg, 44%).

[0271] (4) 122-3 (100 mg, 1 eq) and 3-bromo-2-pyridinecarboxylic acid (61 mg, 1.2 eq) were dissolved in 30 ml of DCM at room temperature, and triethylamine (51 mg, 2 eq) and HATU (145 mg, 1.5 eq) were added in sequence. The mixture was stirred at room temperature overnight. After the intermediate reaction was completed, water and EA were added to the system for extraction. The organic phase was washed three times with saturated sodium chloride solution, and the organic phase was concentrated and purified by normal phase to obtain 122 (46 mg, 20%).

[0272] 7. Synthesis of Compound 129 (cis)

[0273] (1) 2-1 (0.8 g, 1 eq) was dissolved in 20 mL of dioxane at room temperature, and then pinacol diboron (2 eq), potassium acetate (3 eq) and Pd(dppf)Cl2 (0.03 eq) were added in sequence. After the addition was complete, the mixture was protected by nitrogen and heated to 100 °C and stirred overnight. After the intermediate control reaction was completed, the mixture was cooled to room temperature, the insoluble matter was filtered off with celite, and the filtrate was concentrated and purified by normal phase to obtain 129-1 (410 mg, 46%).

[0274] (2) 129-1 (0.41 g, 1 eq) was dissolved in a mixed solution of 20 mL of dioxane and 2 mL of water at room temperature, and then 2-chloro-5-trifluoromethylpyrimidine (2 eq), cesium fluoride (3 eq) and Pd(dppf)Cl2 (0.03 eq) were added in sequence. After the addition was completed, nitrogen was protected, and the temperature was raised to 100°C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature, the insoluble matter was filtered off with celite, and the filtrate was concentrated and purified by normal phase to obtain 129 (cis) (32 mg, 7%).

[0275] 8. Synthesis of Compound 132 (cis)

[0276] 2-1 (200 mg, 1 eq), 132-2 (1.5 eq), and cesium fluoride (3 eq) were dissolved in a mixed solution of 20 mL of dioxane and 2 mL of water at room temperature. Under nitrogen protection, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (9 mg, 0.03 eq) was added. After the addition was complete, the temperature was raised to 100 ° C and stirred overnight. After the intermediate control reaction was completed, the temperature was cooled to room temperature, and the filtrate was concentrated and purified by normal phase to obtain 132 (cis) (50 mg, light yellow solid, 22%).

[0277] 9. Synthesis of Compound 133 (cis)

[0278] (1) Compound 133-1 (54 g, 1 eq) was dissolved in 500 mL of methanol. Sodium borohydride (6.9 g, 1 eq) was added in batches under ice bath conditions. The mixture was stirred in an ice bath for 2 h. After the reaction was completed, 500 mL of aqueous ammonium chloride solution was added and stirred for 5 min. The mixture was extracted with ethyl acetate. The organic phase was dried, concentrated, and mixed. The mixture was purified by normal phase separation (ethyl acetate: petroleum ether = 1:9) to obtain compound 133-2 (17.3 g).

[0279] (2) At room temperature, compound 133-2 (17.3 g, 1 eq) and thionyl chloride (21.7 g, 3 eq) were added to a solution of lithium chloride (10.3 g, 4 eq) in DMF (200 mL) in sequence. The mixture was stirred at room temperature for 3 h. After the reaction was completed, 100 mL of water was slowly added to the reaction solution. The mixture was extracted twice with methyl tert-butyl ether. The organic phase was washed twice with saturated brine, dried and concentrated to obtain crude compound 133-3 (20 g).

[0280] (3) At room temperature, to a solution of potassium hydroxide (18.6 g, 5 eq) in DMSO (200 mL) were added compounds 133-3 (20 g, 1 eq) and 133-4 (14.3 g, 1.1 eq) in DMSO, and the mixture was stirred at room temperature for 3 h. To the reaction solution, an aqueous solution of potassium hydroxide (18.6 g, 5 eq) was slowly added dropwise and stirred at room temperature for 1 h. The reaction was completed by mid-control. The mixture was extracted twice with ethyl acetate, and the organic phases were combined, dried, concentrated, and mixed. The mixture was purified by normal phase purification to obtain compound 133-5 (4.3 g, yield 26%).

[0281] (4) Compound 133-5 (4.3 g, 1 eq) was dissolved in 50 mL of ethanol. Sodium borohydride (2.3 g, 4 eq) was added in batches under ice bath conditions. The mixture was stirred overnight in an ice bath. After the reaction was completed, saturated aqueous ammonium chloride solution (50 mL) was added and stirred for 5 min. The mixture was extracted twice with ethyl acetate. The organic phase was dried and concentrated to obtain compound 133-6 (4.3 g).

[0282] (5) 133-6 (8.0 g, 1 eq) was dissolved in 80 mL of DCM, and Boc anhydride (1.00 eq) and triethylamine (3.00 eq) were added in sequence. The mixture was stirred at room temperature overnight. After the reaction was completed, the sample was directly concentrated and mixed. The product was purified by normal phase purification. The peak with high polarity was selected and concentrated to obtain 133-7 (3.0 g, light yellow oil, yield 38%).

[0283] (6) 133-7 (300 mg, 1 eq), 133-8 (1.5 eq), and cesium fluoride (3 eq) were dissolved in a mixed solution of 20 mL of dioxane and 2 mL of water at room temperature. Under nitrogen protection, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (9 mg, 0.03 eq) was added. After the addition was complete, the temperature was raised to 100 °C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature, and the filtrate was concentrated and purified by normal phase to obtain 133-9 (250 mg, light yellow solid, 56%).

[0284] (7) Compound 133-9 (200 mg, 1.00 eq) was added to a solution of hydrochloric acid in 1,4-dioxane (10.0 mL). After stirring at 20° C. for 2 h, the solvent was removed in vacuo to give compound 133-10 (0.15 g, pale yellow oil, crude product).

[0285] (8) 133-10 (150 mg, 1.00 eq) was dissolved in 10.0 mL of dichloromethane. 133-11 (1.00 eq), triethylamine (3.00 eq), and HATU (2.00 eq) were added sequentially under ice bath conditions. The mixture was stirred at room temperature for 1-2 h. After the reaction was completed, the mixture was extracted with water and dichloromethane. The organic phase was washed three times with dilute hydrochloric acid, dried and concentrated, and purified by normal phase chromatography to obtain 133 (cis) (125 mg, light yellow solid, yield 54%).

[0286] 10. Synthesis of Compound 135 (cis)

[0287] (1) 133-7 (3.0 g, 1 eq), bis(pinacolato)diboron (1.5 eq), and potassium acetate (2 eq) were dissolved in 40 mL of dioxane solution at room temperature. [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.03 eq) was added under nitrogen protection. After the addition was complete, the temperature was raised to 100°C and stirred overnight. After the intermediate control reaction was completed, the temperature was lowered to room temperature. The filtrate was concentrated and purified by normal phase to obtain 135-1 (1.8 g, light yellow oil, yield 52%).

[0288] (2) 135-1 (1.8 g, 1 eq) was dissolved in 20 mL of solvent (dioxane: water = 10:1), and 135-2 (1.2 eq), potassium carbonate (3 eq), and 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (II) dichloromethane complex (0.02 eq) were added in sequence. Under nitrogen protection, the temperature was raised to 100 ° C. and stirred overnight. The reaction was completed in the middle control. The mixture was extracted with water and ethyl acetate three times. The organic phases were combined, dried, concentrated, and mixed. The mixture was purified by normal phase to obtain 135-3 (1.0 g, light yellow solid, yield 96%).

[0289] (3) Compound 135-3 (1.0 g, 1.00 eq) was added to a solution of hydrochloric acid in 1,4-dioxane (20.0 mL). After stirring at 20° C. for 2 h, the solvent was removed in vacuo to obtain compound 135-4 (0.6 g, pale yellow oil, crude product).

[0290] (4) 135-4 (100 mg, 1.00 eq) was dissolved in 10.0 mL of dichloromethane. Under ice bath conditions, 135-5 (1.00 eq), triethylamine (3.00 eq), and HATU (2.00 eq) were added in sequence. The mixture was stirred at room temperature for 1-2 h. After the reaction was completed, the mixture was extracted with water and dichloromethane. The organic phase was washed three times with dilute hydrochloric acid. The organic phase was dried and concentrated, and the sample was purified by normal phase to obtain 135 (cis) (42.0 mg, light yellow solid, yield 26%).

[0291] Biological activity evaluation:

[0292] 1. Nematode 96-well plate assay:

[0293] (1) Preparation of test agents

[0294] Accurately weigh the test drug, dissolve it in DMSO to prepare a stock solution, and dilute it into different concentration gradient solutions.

[0295] (2) Target nematode isolation

[0296] Southern root-knot nematode: When egg masses emerge from root nodes, use tweezers under a dissecting microscope to remove the egg masses from the nodes and place them in clean water. Soak them in a 0.25% sodium hypochlorite solution for approximately 1 minute. After sieving through a 500-mesh sieve, place them in a 90mm Petri dish containing an appropriate amount of tap water. Place the dish in a sieving device and incubate in a 28°C incubator for 3 days. Second-instar larvae will hatch from the egg masses. Observe the nematode suspension under a microscope and dilute it to approximately 1000 nematodes / mL for later use.

[0297] (3) Chemical treatment

[0298] Add 100 μL each of the prepared test agent and nematode suspension to a 96-well culture plate, cover to prevent evaporation, and place in a 28°C incubator. Set up a water control and a test agent control; if a solvent is used, also set up a solvent control.

[0299] (4) Cultivation and observation

[0300] The nematodes treated with the drug were cultured under normal conditions, and the mortality rate of the nematodes was measured after 48 hours and 72 hours: mortality rate (%) = (number of dead worms / number of test worms) * 100. Representative test results are shown in Table 2.

[0301] Table 2 Nematode test results

[0302] Note: N stands for no data, reference compound A:

[0303] At the same time, after many tests, it was found that many of the compounds and compositions described in the present invention have good control activity against different types of nematodes, and have the characteristics of broad spectrum, high efficiency, strong systemic activity, etc., can effectively control pests and / or fungi, and have certain commercial value.

Claims

1. A four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides: in, A1, A2, A3, A4, and A5 independently represent N or CM; Q represents an aryl group or a heterocyclic group; X represents halogen; Y represents hydrogen, alkyl or halogenated alkyl; R1, R2, R3, and M each independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonic acid, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2.-PO(OR 22 )2.-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-Si(R 22 )3. -O(CO)R 22 、-O-(SO2)R 22 、-S(CO)R 22 、-(SO2)OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22 、-(CO)OR 22 、-ON=C(R 23 2. -CR 23 =N-OH or -CR 23 =NOR 22 , wherein the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, nitro, cyano, hydroxyl, thiol, carboxyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2.-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO2)R 22 、-(CO)OR 22 、-O(CO)OR 22 、-Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-alkylene-(CO)OH or -O-alkylene-(CO)OR 22 is substituted by at least one group in; R 21 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic, -OR 22 、-(CO)R 22 、-(CO)OR 22 、-Alkylene-(CO)OR 22 、-(SO2)R 22 、-(SO2)OR 22 、-Alkylene-(SO2)R 22 、-(CO)N(R 24 )2 or -(SO2)N(R 24 )2; R 22 Each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic group, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, cyano, trialkylsilyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic group, -OR 25 、-SR 25 、-O(CO)R 25 、-(CO)R 25 、-(CO)OR 25 OR-O(CO)OR 25 is substituted by at least one group in; R 23 Each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl; R 24 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl; or N(R 21 )2、N(R 24 )2 each independently represents a heterocyclic group with a nitrogen atom at the 1-position; R 25 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, phenyl or phenyl substituted by at least one group selected from the following: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl, phenoxy, or a group selected from halogen, cyano, nitro, A phenoxy group substituted with at least one of an alkyl group, a haloalkyl group, an alkoxy group or a haloalkoxy group; The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-alkylene-(CO)OR 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 Each independently represents hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides according to claim 1, characterized in that: Y represents hydrogen, C1-C8 alkyl or halogenated C1-C8 alkyl; R1, R2, R3, and M each independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2.-PO(OR 22 )2.-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-Si(R 22 )3. -O(CO)R 22 、-O-(SO2)R 22 、-S(CO)R 22 、-(SO2)OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22 、-(CO)OR 22 、-ON=C(R 23 2. -CR 23 =N-OH or -CR 23 =NOR 22 , wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, nitro, cyano, hydroxyl, thiol, carboxyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2.-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO2)R 22 、-(CO)OR 22 、-O(CO)OR 22 、-Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-(C1-C8 alkylene)-(CO)OH or -O-(C1-C8 alkylene)-(CO)OR 22 is substituted by at least one group in; R 21 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic group, -OR 22 、-(CO)R 22 、-(CO)OR 22 、-(C1-C8 alkylene)-(CO)OR 22 、-(SO2)R 22 、-(SO2)OR 22 、-(C1-C8 alkylene)-(SO2)R 22 、-(CO)N(R 24 )2 or -(SO2)N(R 24 )2; R 22 Each independently represents a C1-C8 alkyl, a C2-C8 alkenyl, a C2-C8 alkynyl, a C3-C8 cycloalkyl, a C3-C8 cycloalkenyl, an aryl or a heterocyclic group, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, cyano, tri-C1-C8 alkylsilyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic group, -OR 25 、-SR 25 、-O(CO)R 25 、-(CO)R 25 、-(CO)OR 25 OR-O(CO)OR 25 is substituted by at least one group in; R 23 Each independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxyC1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl; R 24 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenylC1-C8 alkyl; or N(R 21 )2、N(R 24 )2 each independently represents a heterocyclic group with a nitrogen atom at the 1-position; R 25 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, phenyl or phenyl substituted by at least one group selected from the following: halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, phenoxy, or phenoxy substituted by at least one group selected from the following: halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy; The aforementioned "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-(C1-C8 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 They independently represent hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

3. The four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides according to claim 1 or 2, characterized in that: Y represents hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl; R1, R2, R3, and M each independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2.-PO(OR 22 )2.-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-Si(R 22 )3. -O(CO)R 22 、-O-(SO2)R 22 、-S(CO)R 22 、-(SO2)OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22 、-(CO)OR 22 、-ON=C(R 23 2. -CR 23 =N-OH or -CR 23 =NOR 22 , wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, nitro, cyano, hydroxyl, thiol, carboxyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-O(CS)N(R 21 )2、-(SO2)N(R 21 )2、-O(SO2)N(R 21 )2.-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO2)R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO2)R 22 、-(CO)OR 22 、-O(CO)OR 22 、-Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-(C1-C6 alkylene)-(CO)OH or -O-(C1-C6 alkylene)-(CO)OR 22 is substituted by at least one group in; R 21 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic group, -OR 22 、-(CO)R 22 、-(CO)OR 22 、-(C1-C6 alkylene)-(CO)OR 22 、-(SO2)R 22 、-(SO2)OR 22 、-(C1-C6 alkylene)-(SO2)R 22 、-(CO)N(R 24 )2 or -(SO2)N(R 24 )2; R 22 Each independently represents a C1-C6 alkyl, a C2-C6 alkenyl, a C2-C6 alkynyl, a C3-C6 cycloalkyl, a C3-C6 cycloalkenyl, an aryl or a heterocyclic group, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, cyano, tri-C1-C6 alkylsilyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic group, -OR 25 , -SR 25 、-O(CO)R 25 、-(CO)R 25 、-(CO)OR 25 OR-O(CO)OR 25 is substituted by at least one group in; R 23 Each independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl; R 24 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C6 alkyl; or N(R 21 )2、N(R 24 )2 independently represent unsubstituted or substituted by at least one group selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl R 25 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, phenyl or phenyl substituted by at least one group selected from the following: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenoxy, or phenoxy substituted by at least one group selected from the following: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy or halo-C1-C6 alkoxy; The aforementioned "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-(C1-C6 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 Each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; Preferably, A1, A2, A3, A4, A5 each independently represent N or CM, and at most 2 groups are N.

4. The four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides according to any one of claims 1 to 3, characterized in that: A1, A2, A3, A4, A5, R1, R2, R3, X, Y and Q are as defined in any one of claims 1 to 3, and They are cis relative to each other on the four-membered ring.

5. The four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides according to any one of claims 1 to 4, characterized in that: The carbon atoms at positions 1 and 2 of the four-membered ring are both chiral centers, and have a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R), based on the contents of stereoisomers having R and S configurations at these positions, respectively; or Based on the contents of stereoisomers having R and S configurations at this position, respectively, it has a stereochemical purity of 60-100% (S), preferably 70-100% (S), more preferably 80-100% (S), further preferably 90-100% (S), and even more preferably 95-100% (S).

6. The four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides according to any one of claims 1 to 5, characterized in that: The compound is selected from any one of Table 1, Table A, Table B and Table C.

7. A method for preparing the four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides as claimed in any one of claims 1 to 6, comprising the following steps: (1) The compound represented by the general formula II and the compound represented by the general formula III are subjected to a condensation reaction to obtain For the compound shown in general formula I, the reaction equation is as follows: Alternatively, (2) Compound IV and Compound V are coupled to obtain Compound I, and the chemical reaction equation is as follows: Among them, either Z1 or Z2 represents a halogen, and the other represents Substituents A1, A2, A3, A4, A5, R1, R2, R3, X, Y and Q are defined as any one of claims 1 to 6; Preferably, the reaction of steps (1) and (2) is carried out in the presence of a solvent; More preferably, a condensing agent and / or a base is added during the reaction of step (1); or, a catalyst and / or a base is added during step (2); Further preferably, the solvent in steps (1) and (2) is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran, ethyl acetate, toluene or water; the base in steps (1) and (2) is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, etc.) or an organic base (such as DMAP, pyrazole, triethylamine, DIEA, etc.); the condensing agent in step (1) is selected from at least one of Py-BOP, At least one of Py-AOP, EDCI, HOBT, DCC, HBTU or HATU; the catalyst in step (2) is selected from at least one of Pd(dppf)Cl2, Pd(PPh3)4, PdCl2, Pd(OAc)2, Pd(PPh3)2Cl2, NiCl2(dppf) and PdCl2(dppf)·CH2Cl2.

8. A composition for killing pests and / or fungi (especially nematodes), characterized in that: A composition comprising a biologically effective amount of a four-membered ring amide compound according to any one of claims 1 to 6, its stereoisomers / isomers / enantiomers / salts and N-oxides; preferably, a formulation adjuvant; more preferably, other active ingredients.

9. A method for controlling harmful organisms and / or fungi (especially nematodes), characterized in that: The method comprises contacting the harmful organisms and / or fungi or their environment with a biologically effective amount of the four-membered ring amide compound described in any one of claims 1 to 6, its stereoisomers / isomers / enantiomers / salts and N-oxides or the composition described in claim 8.

10. Use of the four-membered ring amide compound according to any one of claims 1 to 6, its stereoisomers / isomers / enantiomers / salts and N-oxides or the composition according to claim 8 in controlling harmful organisms and / or fungi (especially nematodes).

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