Four-membered ring amide compound and application thereof

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a four-membered ring amide compound as well as a stereoisomer / isomer / enantiomer / salt and N-oxide thereof and application of the four-membered ring amide compound and the stereoisomer / isomer / enantiomer / salt and N-oxide. The compound is shown as a general formula I: # imgabs0 #, wherein Q represents aryl or heterocyclic group; y represents halogen; x represents halogen, nitro, cyano and the like; r1, R2, R3, R4 and R5 independently represent hydrogen, halogen, nitro and the like. The compound has an excellent control effect on pests and / or fungi (especially nematodes).

Description

Technical Field

[0001] The invention belongs to the technical field of pesticides, and specifically 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 or fungicides, pests and diseases have acquired drug resistance and become difficult to control with the existing insecticides or fungicides. In addition, some of the known pest control agents are highly toxic, or some of them damage the ecosystem through their long-term residual properties. In this case, although a large number of nematicides are known, such as WO2013143811A1 discloses N-cyclic amide compounds and their use as nematicides, there is still a need to develop new pest control agents with low toxicity and low residual properties. Summary of the invention

[0003] In order to solve the above problems existing in the prior art, the present invention provides a four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides, wherein the compound has excellent control effect on harmful organisms and / or fungi (especially nematodes).

[0004] The technical solution adopted by the present invention is as follows:

[0005] A four-membered ring amide compound, its stereoisomers / isomers / enantiomers / salts and N-oxides:

[0006]

[0007] Wherein, Q represents an aryl group or a heterocyclic group;

[0008] Y represents halogen;

[0009] X represents halogen, nitro, cyano, thiocyano, hydroxyl, mercapto, 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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2、-PO(OR 22 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-Si(R 22 ) 3 、-O(CO)R 22 、-O-(SO 2 )R 22 、-S(CO)R 22 、-(SO 2 )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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO 2 )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;

[0010] R 1 , R 2 , R 3 , R 4 , R 5 Each of the following independently represents hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonate, 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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-PO(OR 22 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-Si(R 22 ) 3 、-O(CO)R 22 、-O-(SO 2 )R 22 、-S(CO)R 22 、-(SO 2 )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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO 2 )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;

[0011] 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 、-(SO 2 )R 22 、-(SO 2 )OR 22 、-alkylene-(SO 2 )R 22 、-(CO)N(R 24 ) 2 or-(SO 2 )N(R 24 ) 2 ;

[0012] 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;

[0013] R 23 Each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl;

[0014] R 24 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl;

[0015] or N(R 21 ) 2 、N(R 24 ) 2 Each independently represents a heterocyclic group with a nitrogen atom at the 1-position;

[0016] 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 or phenoxy substituted by at least one group selected from the following: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy;

[0017] The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclic", "non-aromatic heterocyclic" 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 、-(SO 2 )R 10 、-N(R 10 ) 2 or -O-alkylene-(CO)OR 10or two adjacent carbon atoms on the ring are substituted with -OCH 2 CH 2 -or-OCH 2 O- forms a fused ring;

[0018] 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.

[0019] In a specific embodiment, X represents halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonate, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, 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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-PO(OR 22 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-Si(R 22 ) 3 、-O(CO)R 22 、-O-(SO 2 )R 22 、-S(CO)R 22 、-(SO 2 )OR 22 、-O(CO)OR 22 、-(CO)(CO)OR 22 、-(CO)OR 22 、-ON=C(R 23 ) 2 , -CR 23 =N-OH or -CR23 =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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO 2 )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;

[0020] R 1 , R 2 , R 3 , R 4 , R 5 Each of the following independently represents hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, mercapto, 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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-PO(OR 22 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-Si(R 22 ) 3 、-O(CO)R 22 、-O-(SO 2 )R 22 、-S(CO)R 22 、-(SO 2 )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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )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-(SO 2 )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;

[0021] 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 、-(SO 2 )R 22 、-(SO 2 )OR 22 、-(C1-C8 alkylene)-(SO 2 )R 22 、-(CO)N(R 24 ) 2 or-(SO 2 )N(R 24 ) 2 ;

[0022] 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;

[0023] R23 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;

[0024] 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;

[0025] or N(R 21 ) 2 、N(R 24 ) 2 Each independently represents a heterocyclic group with a nitrogen atom at the 1-position;

[0026] 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 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;

[0027] The aforementioned “C3-C8 cycloalkyl”, “C3-C8 cycloalkenyl”, “heterocyclyl”, “non-aromatic 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 、-(SO 2 )R 10 、-N(R 10 ) 2 or -O-(C1-C8 alkylene)-(CO)OR10 or two adjacent carbon atoms on the ring are substituted with -OCH 2 CH 2 -or-OCH 2 O- forms a fused ring;

[0028] 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.

[0029] In another embodiment, X represents halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonate, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, 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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-PO(OR 22 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-Si(R 22 ) 3 、-O(CO)R 22 、-O-(SO 2 )R 22 、-S(CO)R 22 、-(SO 2 )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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO 2 )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;

[0030] R 1 , R 2 , R 3 , R 4 , R 5 Each of the following independently represents hydrogen, halogen, nitro, cyano, thiocyano, 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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-PO(OR 22 ) 2 、-OR 22 、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-Si(R 22 ) 3 、-O(CO)R 22 、-O-(SO 2 )R 22 、-S(CO)R 22 、-(SO 2 )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 、-(SO 2 )N(R 21 ) 2 、-O(SO 2 )N(R 21 ) 2 、-OR 22、-(CO)R 22 、-SR 22 、-(SO)R 22 、-(SO 2 )R 22 、-O(CO)H、-O(CO)R 22 、-O-(SO 2 )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;

[0031] 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 、-(SO 2 )R 22 、-(SO 2 )OR 22 、-(C1-C6 alkylene)-(SO 2 )R 22 、-(CO)N(R 24 ) 2 or-(SO 2 )N(R 24 ) 2 ;

[0032] 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 25OR-O(CO)OR 25 is substituted by at least one group in;

[0033] 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;

[0034] 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;

[0035] or N(R 21 ) 2 、N(R 24 ) 2 Each independently represents an unsubstituted or substituted group selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl.

[0036] 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 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;

[0037] The aforementioned “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl”, “non-aromatic 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 、-(SO 2 )R 10 、-N(R 10 ) 2 or -O-(C1-C6 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring are substituted with -OCH 2 CH 2 -or-OCH 2 O- forms a fused ring;

[0038] 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.

[0039] In the definition of the compounds represented by the above general formula and in all the following structural formulae, 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, in the compound word "-O-alkylene-(CO)OH", the alkyl group can be -CH 2 -、-CH 2 CH 2 -、-CH(CH 3 )-、-C(CH 3 ) 2 - etc. Alkyl groups are, 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-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but-3-ene-1-yl, 1-methylbut-3-ene-1-yl and 1-methylbut-2-ene-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system with, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl with, for example, three to six carbocyclic ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bond can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0040] 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

[0041] etc., also including but not limited to heteroaryl, i.e. aromatic cyclic groups 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 among the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0042]

[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 those mentioned. In addition, identical or different substitution characters contained in identical or different substituents are independently selected and may be identical or different. The same applies to ring systems formed by different atoms and units. At the same time, the scope of the claims will exclude compounds that are known to the person skilled in the art to be chemically unstable under standard conditions.

[0044] In addition, unless otherwise specified, the term "substituted by at least one group" in the present invention means substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without specific connection positions 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]

[0047] Among them, R 1 , R 2 , R 3 , R 4 , R 5 , X, Y and Q are defined as above, and They are cis relative to each other on the four-membered ring.

[0048] 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:

[0049]

[0050] Among them, the substituent R 1 , R 2 , R 3 , R 4 , R 5 , 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 with R and S configurations at these positions, respectively.

[0051] 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:

[0052]

[0053] Among them, the substituent R 1 , R 2 , R 3 , R 4 , R 5 , X, Y and Q are as defined above; the carbon atoms at positions 1 and 2 on the four-membered ring are both 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 with R and S configurations at these positions, respectively.

[0054] 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.

[0055] 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 mention is made of stereochemical details in each case. The present invention therefore encompasses all such isomers and tautomers and their mixtures in all proportions, together with isotopic forms, such as deuterated compounds.

[0056] The present invention also encompasses salts or N-oxides of each compound of formula I.

[0057] Those of ordinary skill in the art also understand that since salts of compounds are 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 form.

[0058] Therefore, various salts of the compounds of the present invention (and the active ingredients used in combination with the active ingredients of the present 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.

[0059] Suitable among the agriculturally and / or physiologically tolerable salts are also cationic salts which do not adversely affect the pesticidal and / or parasiticidal action of the compounds of formula I. Thus, particularly suitable cations are ions of alkali metals including sodium, potassium and lithium, ions of alkaline earth metals including calcium and magnesium, and ions of transition metals including manganese, copper, iron, zinc, cobalt, lead, silver, nickel; and also ammonium or organoammonium 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.

[0060] The compounds of formula I can exist in different tautomeric forms. The present invention encompasses all those tautomeric forms and mixtures thereof.

[0061] Diastereomeric mixtures or mixtures of racemates of compounds of formula I in free or salt form, which may be obtained depending 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.

[0062] Enantiomeric mixtures (e.g. racemates) can be obtained by a similar process and they 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 according to 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).

[0063] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of appropriate isomer mixtures but also by generally known diastereoselective or enantioselective synthetic methods, for example by carrying out the method according to the invention using a starting material of an appropriate stereochemistry.

[0064] The compounds of the invention can be reacted with a suitable oxidizing agent (e.g., H 2 O 2 / urea adduct) in the presence of anhydride (e.g., trifluoroacetic anhydride) to prepare N-oxides. 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.

[0065] 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.

[0066] The compounds of the 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 further solvents, such as those which can be used for the crystallization of compounds present in solid form.

[0067] 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:

[0068] The compound represented by the general formula II is reacted with the compound represented by the general formula III or its amine salt (such as hydrochloride) to obtain the compound represented by the general formula I, and the reaction equation is as follows:

[0069]

[0070] Wherein, M represents OH or halogen, and the substituent R 1 , R 2 , R 3 , R 4 , R 5 , X, Y and Q are defined as above.

[0071] In one embodiment, the reaction is carried out in the presence of a solvent.

[0072] In another embodiment, a condensing agent and / or a base is added during the reaction.

[0073] In a specific embodiment, the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane (DCM) or ethyl acetate.

[0074] In one embodiment, the base is selected from an inorganic base (such as K 2 CO 3 、Na 2 CO 3 , Cs 2 CO 3 ,

[0075] NaHCO 3 ,KF,CsF,KOAc,AcONa,K 3 PO 4,t-BuONa,EtONa,NaOH,KOH,

[0076] At least one of an organic base (such as NaOMe, etc.) or an organic base (such as pyrazole, triethylamine, DIEA, etc.).

[0077] In a specific embodiment, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT (1-hydroxybenzotriazole), DCC, HBTU or HATU.

[0078] In addition, the compound represented by the general formula I can also be prepared by referring to the methods shown in WO2015003951 A1, WO2013143811A1, etc.

[0079] 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.

[0080] In a specific embodiment, the composition further comprises a formulation aid.

[0081] In another specific embodiment, the composition further comprises other effective ingredients.

[0082] The present invention also provides a method for controlling harmful organisms and / or fungi (especially nematodes), comprising contacting the harmful organisms and / or fungi (especially nematodes) 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.

[0083] The present invention also provides the use of the four-membered ring amide compound, its stereoisomer / isomer / enantiomer / salt and N-oxide or the composition in preventing and controlling harmful organisms and / or fungi (especially nematodes).

[0084] It has been found that compounds of formula I, I', I" or I'" are useful for controlling damage caused by pests and / or fungi.

[0085] In one embodiment, the compound of Formula I, I', I", or I'" may be used in agriculture.

[0086] Therefore, the present invention is further 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 pests, to the locus of the pests, or to plants susceptible to attack by pests and / or fungi or to plant propagation material.

[0087] 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, still protecting against these harmful organisms.

[0088] 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. They can be used against pests and / or fungi resistant to pesticides even at low application rates. 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.

[0089] 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 reduced egg laying and / or hatching rates, good activity corresponding to a destruction rate (mortality) of at least 50% to 60%.

[0090] It has now been found that the compounds of 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 formula I, I', I" or I'"'.

[0091] The compounds of formula I, I', I" or 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, Meloidogynearenaria 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; Stingnematodes, Eelonolaimus longicaudatus, and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; Ringnematodes, Criconema species, Criconemella species, Criconemoides species, 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, nematodes), Nacobbus species; Needle nematodes, Longidoruse longatus and other Longidorus species; Pinnematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus gibberellus;

[0092] 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; Daggernematodes, Xiphinema species; and other plant-parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

[0093] In particular, the following nematode species can be controlled by the compounds according to the invention: Meloidogyne spp., Heterodera spp., Spirodactyle spp. and Pratylenchus spp.

[0094] Examples of animal pests are:

[0095] - From the order Acarina, for example,

[0096] Acalitus spp., Acalitus spp., Acaricalus spp., Aceria spp., Acarina ...

[0097] - From the order Phthinidae, for example,

[0098] Haematoptes, Longignathus, Human lice, Pemphigus, and Psyllids;

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

[0100] Amphimallon majale, Amphimallon majale, Oriental beetle, Amphimallon, 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 sugar beetle, Coffee berry beetle, Lagria vilosa, Potato beetle, Rice water beetle, Liogenys spp., Maecolaspis spp., Chestnut beetle, American leaf beetle (Megascelis spp.), Melighetes aeneus, Myochrous armatus, saw-toothed beetles, Otiorhynchus spp., horned beetles, spotted beetles, beetles, rape flea beetles, Rhyssomatus aubtilis, root beetles, scarab beetles, rice weevils, wheat moths, pseudo-root beetles, Sphenophorus spp., soybean stem weevils, pseudo-walkers, pseudo-castanum, and trogoderma;

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

[0102] 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 oligochaete, Drosophila melanogaster, Drosophila spp., Gastrocera spp., Geomyza tripunctata, Glossina spp., Dermatophagus spp., Liriomyza spp., Liriomyza spp., Lucilia spp., Liriomyza spp., Musca domestica spp., Liriomyza spp., Swedish straw fly, Chenopodiaceae, Grass fly spp., Bactrocera spp., Rivelia quadrifasciata, Scatella spp., Fungus gnats, Spiny flies, Tabanus spp., Taenia spp. and Crane fly spp.;

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

[0104] Acanthocoris scabrator, Amblypelta nitida, Bathycoelia thalassina, Acanthocoeli, Clavigrallatomentosicollis, Creontiades spp., Dichelops furcatus, Edessa spp., Euchistus spp., Eurydemapulchrum, Amblypelta nitida, Horcias nobilellus, Acanthocoeli, Lygus, Murgantia, 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., Trypanosoma spp., Cassava web stink bug (Vatiga illudens);

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

[0106] Aphids, Adalges spp., Agallina ensigera, Agonascena targionii, Aleurodicus spp., Aleurocanthus spp., Sugarcane hole whitefly, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinson, Scale spp., Aphididae, Aphid, Scale spp., Aphids, Bactericera cockerelli, Aleurodicus spp., Brachycaudus spp., Cabbage aphid, Cavariella aegopodii Scop.), wax scale, brown round scale, net-seed grass leaf round scale, Cicadella spp., large white leafhopper (Cofana spectra), cryptomere aphid, Cicadulina spp., brown soft scale, corn yellow-winged leafhopper, naked whitefly spp., citrus psyllid, wheat two-tailed aphid, western round tail aphid, small green leafhopper spp., apple aphid, grape leafhopper spp., wax clam spp., red eucalyptus psyllid (Glycaspis brimblecombei), vegetable aphid, large tail aphid (Hyalopterus spp.), super tumor aphid species, lemon fruit green leafhopper (Idioscopus clypealis), Jacobiasca lybica, Laodelphax, ball-hard scale, oyster shield scale spp., radish aphid (Lopaphis erysimi), Lyogenys maidis, long-tube aphid, Mahanarv spp., Metcalfa pruinosa), wheat aphid, Myndus crudus, aphid spp., Taiwan leek aphid, black-tailed leafhopper spp., brown planthopper spp., pear green aphid, Odonaspis ruthae, parasitic sugarcane aphid, bayberry whitefly, Caulis psyllid, shield scale spp., gall aphid spp., corn wax cicada, flat-horned planthopper spp., hop wart aphid, phylloxera spp., Mobilococcus spp., white shield scale spp., mealybug spp., cotton blind bug (Pseudatomoscelis seriatus), psyllid spp., cotton scale (Pulvinaria aethiopica), round shield scale spp., Quesada gigas, electric leafhopper (Recilia dorsalis), constriction aphid spp., black helmet scale spp., banded leafhopper spp., two-forked aphid spp., wheat aphid (Sitobion spp.), white-backed planthopper, Spissistilus festinus, Tarophagus Proserpina, aphids, whiteflies, Tridiscus sporoboli, Trionymus spp., African psyllids, orange-arrow scale, Zyginaflammigera, Zyginidia scutellaris;.

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

[0108] Arge spp., Arge spp., Argetotermes ...

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

[0110] Coptotermes, Corniternes cumulans, Coptotermes, Macrotermes, Macrotermes, Microtermes, Reticulitermes; tropical fire ants

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

[0112] Long-winged torrefies, brown-banded torrefies, transparent-winged moth, ground moth, cotton leafworm, Amylois spp., bean armyworm, yellow torrefies, silver moth (Argyresthia spp.), band torrefies, yarrow-shaped torrefies, cotton miner, corn armyworm, powdery moth, peach fruit moth, grass borer, leaf roller, Chrysoteuchia topiaria, grape fruit borer, leaf roller, cloud torrefies, pattern torrefies, sheath moth, lepidoptera, Cosmophila flava, grass borer, cabbage borer, apple heteromorphic torrefies, boxwood moth, torrefies, boxwood moth, stem borer, Sudan bollworm, diamond drill, African stem borer, powder borer, leaf torrefies (Epinotia spp.), Etiella zinckinella, Etiella spp., Etiella spp., Etiella spp., Etiella spp., Etiella spp., Etiella spp., Feltia jaculiferia, Grapholita spp., Echinodermata, Spodoptera spp., Herpetogramma spp., Herpetogramma spp., Herpetogramma spp., Lasmopalpus lignosellus, Lasmopalpus lignosellus, Herpetogramma spp., Herpetogramma spp., Loxostege bifidalis, Herpetophaga spp., Herpetogramma ... spp., Noctua, Fall Geometrid, Orniodesindica, European corn borer, Microcodina, Brown Geometrid, Small-eyed Spodoptera, Stem borer, Pectinophoragossypiela, Coffee leafminer, One-star armyworm, Potato moth, Pieris rapae, Pieris spp., Diamondback moth, Bud moth, Geometrid, Peppermint moth, Richia albicosta, Scirpophaga spp., Stem borer, Long-palped Geometrid, Spodoptera, Cotton leaf folder, Xingpengwei, Heteropoda, Leaf folder, Cabbage looper, Tomato leafminer, and Lymantria spp.;

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

[0114] Damalina spp. and Trichodesmosis spp.;

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

[0116] Blatta, Blattella, Gryllotalpa, Madeira Blattella, Locusta, American Gryllotalpa (Neocurtillahexadactyla), Periplaneta, Scapteriscus spp. and Desert Locust;

[0117] - From the order of the Rodentia, for example,

[0118] Booklice;

[0119] - from the order Siphonaptera, for example,

[0120] Ceratophyllum, Ctenophora and Xenophyllum;

[0121] - from the order Thysanoptera, for example,

[0122] Calliothrips phaseoli, Flower Thrips spp., Sun Thrips spp., Brown-banded Thrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Banded Thrips spp., Thrips spp.;

[0123] - from the order Thysanura, for example,

[0124] Silverfish.

[0125] In another aspect, the invention also relates to a method for controlling or preventing useful plants from being infested with phytopathogenic microorganisms, wherein a compound of formula I, I', I" or I'" is applied as an active ingredient to the plants, their parts or their locus. The compounds of 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 to protect a wide variety of useful plants. The compounds of 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 different 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.

[0126] Examples of fungi include: Deuteromycetes (e.g., Botrytis, Pyrospora, Helminthosporium, Fusarium, Septoria, Cercospora, and Alternaria); Basidiomycetes (e.g., Rhizoctonia, Puccinia, Puccinia); Ascomycetes (e.g., Venturia and Powdery Mildew, Monocystis, Moniliformis, Uncinaria); Oomycetes (e.g., Phytophthora, Pythium, Monoparacephala); Zygomycetes (e.g., Rhizopus); those of the Pucciniaceae family, particularly those of the genus Puccinia, such as Puccinia pachyrhizi, which is also known as Asian soybean rust, and those of the Pucciniaceae family, particularly those of the genus Puccinia, 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.

[0127] 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:

[0128] -Wheat, for the control of the following seed diseases: Fusarium (Fusarium nivale and Fusarium roseum), black bunt (Tilletia tritici, Tinderella dwarfa or Tilletia indica), Septoria (Septoria glumae) and Ustilago sphaeroides;

[0129] - wheat, for the control of the following diseases of the aerial 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 specietritici), rust (Puccinia striatum and Puccinia reconditatis) and Septoria diseases (Septoria tritici and Septoria glumenifolia);

[0130] - 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 (Pyrrhizalium trichomoniasis, Pyrrhizalium teres and Cochliobolus graminis), loose smut (loose smut) and fusarium (Fusarium nivale and Fusarium roseum);

[0131] - barley, for the control of the following diseases of the aerial parts of the plant: cereal eyespot (Tapesia yallundae), net blotch (Pyrrhiza terrestris and Cochlosporium graminearum), powdery mildew (Erysiphe graminis formas pecie hordei), dwarf leaf rust (Puccinia hordei) and leaf spot (Puccinia hordei);

[0132] - Potatoes, for the control of tuber diseases (particularly Aralia solani, Phomatuberosa, Rhizoctonia solani, Fusarium solani), mildew (Phytophthora infestans) and some viruses (Virus Y);

[0133] - Potatoes, for the control of the following foliar diseases: early blight (Alternaria solani), mildew (Phytophthora infestans);

[0134] - 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 (Tricholoma radix);

[0135] - protein-producing plants, such as peas, for the control of the following seed diseases: anthracnose (Psora foetida, Mycosphaeria pisum), fusarium (Fusarium oxysporum), gray mold (Botrytis cinerea) and mildew (Peronospora oleracea);

[0136] - Oil-containing plants, such as rapeseed, for the control of the following seed diseases: Stemophyton oleraceus, Alternaria brassicae, and Sclerotinia sclerotiorum;

[0137] - Corn, for the control of a variety of seed diseases: (Rhizopus, Penicillium, Trichoderma, Aspergillus, and Gibberella);

[0138] - Flax, for controlling this seed disease: Alternaria linicola;

[0139] - Deep forest trees, for controlling damping-off diseases (Fusarium oxysporum, Rhizoctonia solani);

[0140] - Rice, for the control of the following diseases of the above-ground parts: blast (Pyricularia oryzae), bordered sheath spot (Rhizoctonia solani);

[0141] - Leguminosae, 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.);

[0142] - Leguminosae, for the control of the following diseases on aerial parts: gray mold (Botrytis spp.), powdery mildew (especially Erysiphe spp., Erysiphe spp. and Pyricularia spp.), Fusarium spp. (Fusarium oxysporum, Fusarium rosobasidium), leaf spot (Cladosporium spp.), Alternaria leaf spot (Alternaria spp.), anthracnose (Colletotrichum spp.), Septoria leaf spot (Septoria spp.), black spot (Rhizoctonia solani), mildew (e.g. Peronospora spp., Peronospora spp., Pseudocoperonospora spp., Phytophthora spp.);

[0143] - fruit trees, for the control of various diseases of the aerial parts: candidiasis (Moniliafructigenae, M.laxa), scab (Viburnum inermis), powdery mildew (Moniliaceum alba); - vines, for the control of the following foliar diseases: in particular gray mold (Botrytis cinerea), powdery mildew (Uncinaria vitis), black rot (Guignardia biwelli) and mildew (Plasmopara viticola);

[0144] - Beetroot, for the following diseases of aerial parts: cercospora blight (brown blight of beet), powdery mildew (Erysiphe beticola), leaf spot (Erysiphe beticola).

[0145] 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 comprises contacting 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.

[0146] 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, and they can also be used in combination with other biologically active 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 the form of pesticides with other pesticides often results in a wider spectrum of pesticidal action. For example, the compounds of the present invention having formula I, I', I" or I"' can be effectively combined or used in combination with the following compounds, which are pyrethroids, neonicotinoids, macrocyclic lactones, diamides, phosphates, carbamates, cycloadienes, formamidines, phenolic tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pyrroles and the like.

[0147] By adding, for example, one or more insecticidal, acaricidal, nematicidal and / or fungicidal active agents, the activity of the compositions according to the invention can be significantly broadened and adapted to the prevailing environment. The combination of a compound of formula I, I', I" or I"' with other insecticidal, acaricidal, nematicidal and / or fungicidal active agents can also have further, unexpected advantages, which can also be described as synergistic activities in a broader sense. For example, plants tolerate them better, their phytotoxicity is reduced, harmful organisms or fungi can be controlled at different stages of their development or behave better during their production (for example, during grinding or mixing, during their storage or during their use).

[0148] The following list of pesticides together with the compounds which can be used according to the invention is intended to illustrate the possible combinations by way of example.

[0149] The following combination of a compound of formula I, I', I" or I'" with another active compound is preferred (the abbreviation "TX" means "a compound selected from the 72 compounds of each of Table 1, Table A, Table B and Table C of the present invention"):

[0150] An adjuvant, the adjuvant is selected from the substances consisting of petroleum + TX,

[0151] 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-chlorophenylphenyl sulfone+TX, avermectin+TX, acetoquinone+TX, acetothrin+TX, fluthrin+TX, aldicarb+TX, aldicarb+TX, α-cypermethrin+TX, thiothion+TX, sulfamethoxam+TX, aminothioate+TX, amitriptyline+TX, amitriptyline hydrogen oxalate

[0152] +TX, amitraz+TX, cypermethrin+TX, arsenic trioxide+TX, AVI382+TX, AZ60541+TX, azinphos+TX, azinphos-methyl+TX, azobenzene+TX, azacyclotin+TX, azothoate+TX, benoxafos+TX, benzoximate+TX, benzyl benzoate+TX, bifenazate+TX, flumethrin+TX, binachlor+TX, bromethrin+TX, bromocyclene+TX, bromophos+TX, ethyl bromophos+TX,Bromopropylate + TX, Buprofezin + TX, Butanone + TX, Butanone sulfone + TX, Butanone + TX, butylpyridaben + TX, 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, chlorfenson + TX, Chlorfensulphide + TX, chlorobenzilate + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chlorpyrifos + TX, methyl chlorpyrifos + TX, chlorthiophos + TX, cinerin I + TX, cinerin II + TX, cinerin (cinerins) + TX, clofenac + TX, closantel + TX, kumaphos + TX, crotamiton + TX, crotoxyphos + TX, thiophene + TX, cyanthoate + TX, cyfluthrin [400882-07-7] + TX, cyhalothrin + TX, cypermethrin + TX, DCPM + TX, DDT + TX, demephion + TX, demephion-O + TX, demephion-S + TX, demeton )+TX, methyl demeton+TX, demeton-O+TX, methyl demeton-O+TX, demeton-S+TX, methyl demeton-S+TX, demeton-S-methylsulphon+TX, fenthion+TX, dialifos+TX, diazinon+TX, benzylfluanid+TX, dichlorvos+TX, dicliphos+TX, kailesan+TX, dicrotophos+TX, perdixon+TX, dimefox+TX, dimethoate,

[0153] +TX, dinactin +TX, dinex +TX, dinex-diclexine +TX, dinobuton +TX, dinocap +TX, dinocap-4 +TX, dinocap-6 +TX, dinitro +TX, dinopenton +TX, dinosulfon +TX, dinoterbon +TX, dioxathir +TX, diphenyl sulfone +TX, disulfiram +TX, disulfothion +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, Fenazaquin + TX, Fenbutatinoxide + TX, Fenothiocarb + TX, Fenpropathrin + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenson + TX, Fentifan il)+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, anti-mite+TX, anti-mite hydrochloride+TX, formophos+TX thion)+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, rufenalon+TX, malathion+TX,malonoben + TX, mecarbam + TX, mephosfolan + TX, methacrifos + TX, methamidophos + TX, methidathion + TX, methiophos + TX, methiocarb + TX, methicillin + TX, methomyl + TX, methyl bromide + TX, metolcarb + TX, mexacarbate + TX, milbemycin + TX, milbemycin oxime 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, omethoate (Oxydemeton) + TX, oxamyl + TX, oxydeprofos + TX, oxydisulfoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, petroleum + TX, fenthion + TX, fenthion + TX, chlorpyrifos + TX, phosphamidon + TX, phosfolan + TX, phosmet + TX, phosphamidon + TX, phoxim + TX, methyl pirimiphos + TX, polychloroterpenes + TX, acaricide (polynactins) + TX, proclonor + TX, probromophos + TX, promacyl + TX, propetamphos + TX, propoxur + TX, prothidathion + TX, prothoate + TX, pyrethrins + TX, pyridaphenthion + TX, pyrimidine ... yrimidifen + 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, terbam + TX, stirofos + TX, tetradifon + TX, tetranactin + TX, tetrasul + TX, thiafenox + TX, thiocarboxime + TX, thiocarboxime + TX, fanox)+TX, thiometon+TX, chlorpyrifos+TX, thuringiensin+TX, triamiphos+TX, triarathene+TX, triazophos+TX, triazuron+TX, trichlorfon+TX, trifenofos+TX, trinactin+TX, chlorpyrifos+TX, vaniliprole and YI-5302+TX,

[0154] An algaecide, which is selected from the group consisting of the following substances: 3-benzo[b]thiophene-2-yl-5,6-dihydro-1,4,2-oxathiazine-4-oxide+TX, copper dioctanoate+TX, copper sulfate+TX, cybutryne+TX, dichlone+TX, dichlorophene+TX, endorphin+TX, fentin+TX, slaked lime+TX, nabam+TX, quinoclamine+TX, quinonamid+TX, simazine+TX, fentin acetate and fentin hydroxide+TX,

[0155] An anthelmintic agent, the anthelmintic agent is selected from the following group: avermectin + TX, clefosinate + TX, doramectin + TX, emamectin + TX, emamectin benzoate + TX, eprinomectin + TX, ivermectin + TX, milbemycin

[0156] +TX, moxidectin +TX, piperazine +TX, selamectin +TX, spinosad and thiophanate +TX,

[0157] An avicide, which is selected from the group consisting of chloralose + TX, endrin + TX, fenthion + TX, pyridin-4-amine and strychnine + TX,

[0158] A bactericide, which is composed of substances selected from the following group: 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 di(dimethyldithiocarbamate)+TX, nitrapyrin+TX, octhilinone+TX, oxolinic acid+TX, oxytetracycline+TX, potassium hydroxyquinoline sulfate+TX, probenazole+TX, streptomycin+TX, streptomycin sesquisulfate+TX, chlorphenamine+TX, thimerosal+TX,

[0159] 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+TX 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

[0160] 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.

[0161] megidis+TX, Hippodamia convergens+TX, Leptomastix dactylopii+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, Metaphycus helvolus+TX, Metarhizium

[0162] anisopliae var. acridum+TX、Metarhizium anisopliae var. anisopliae+TX、Neodiprion sertifer nuclear polyhedrosis virus and N. lecontei nuclear polyhedrosis virus+TX、Pseudomonas aeruginosa+TX、Paecilomyces fumosoroseus+TX、Pasteuria thornei+TX、Pasteuria nishizawae+TX、Pasteuria ramosa+TX、Phytoseiulus persimilis+TX、Spodopterae xiguamulticapsid 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,

[0163] A soil disinfectant selected from the group consisting of methyl iodide and methyl bromide + TX,

[0164] A chemical sterilant, the chemical sterilant is selected from the group consisting of the following substances: 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,

[0165] An insect pheromone, the insect pheromone is selected from the group consisting of the following substances: (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-ene-1-al + TX, (Z)-tetradec-9-ene-1-ol + TX, (Z)-tetradec-9-ene-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-ketone + TX, α-multistriatin + TX, western pine beetle aggregation pheromone (brevicomin) + TX, dodecadienoic acid 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, 10-10-dien-1-yl acetate+TX, dominicalure+TX, 4-methyloctanoic acid ethyl ester+TX, eugenol+TX, southern pine beetle aggregation pheromone (frontalin)+TX, gossyplure+TX, grandlure+TX, grandlure mixture I+TX, grandlure mixture II+TX, Ene mixture III + TX, Ene 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, 2,13-diene-1-yl acetate + TX, 18-3,13-diene-1-yl acetate + TX, orfralure + TX, oryctalure + TX, ostramone + TX, siglure + TX, sordidin + TX, sulcatol + TX, tetradecan-11-ene-1-yl acetate + TX, tert-butyl ketone + TX, tert-butyl ketone A + TX, tert-butyl ketone B, 1 +TX, tert-butyl ketone B 2 +TX, tert-actin C and trunc-call+TX,

[0166] An insect repellent, the insect repellent is selected from the group consisting of the following substances: 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 hydroxypiperidin+TX,

[0167] An insecticide, the insecticide is selected from the group consisting of the following substances: 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-dichloropropylene + 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-isovaleryl indan-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-xylyl methylcarbamate+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate+TX, avermectin+TX, acephate+TX, pyridinium Amitraz + TX, domestica + TX, acetothionil + TX, flumethrin + TX, acrylonitrile + TX, cotton boll carb + TX, aldicarb + TX, aldicarb + TX, chlorfenapyr + TX, allethrin + TX, alloamicin + TX, cypermethrin + TX, α-cypermethrin + TX, α-ecdysone + TX, aluminum phosphide + TX, thiothion + TX, thioamide + TX, cypermethrin + TX, amitriptyline + TX, amitriptyline hydrogen oxalate + TX, amitraz + TX, neonicotinoid + TX, ethyl methidathion + TX, AVI382 + TX, AZ60541 + TX, azadirachtin + TX, methyl pyriphos + TX, azinphos-methyl + TX, azophos + TX, Bacillus thuringiensis Bacterial δ-endotoxins + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, fumonisin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, benfentacarb + TX, benfentacarb + TX, insecticide + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bifenthrin + TX, bio-allethrin + TX, bio-allethrin S-cyclopentenyl isomer + TX, bioethanomethrin + TX, bio-permethrin + TX, pyrethrin + TX, di(2-chloroethyl) ether + TX, bistrifluan + TX, borax + TX, bromethrin + TX, bromophenazone + TX, bromo-DDT + TX,Bromophos + TX, bromophos-ethyl + TX, thiamethoxam + TX, buprofezin + TX, cypermethrin + TX, butathiofos + TX, butanone + TX, butyl phosphine + TX, butanone sulfone + TX, butyl pyridaben + TX, cadusofos + 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 + TX, carbofuran + TX, carbofuran hydrochloride + TX, sivaldin + TX, bornyl + TX, chlordane + TX, chlorfenapyr + TX, chlordane + TX, chlorfenapyr + TX, chlorfenapyr hydrochloride + TX, chloroxyphos + TX, chlorfenapyr + TX, Fenpyridamole + TX, chlorpyrifos + TX, chloroform + TX, chloropicrin + TX, chlorpyrifos + TX, chlorpyrifos-methyl + TX, chlorpyrifos + TX, chlorpyrifos + TX, chloranil + TX, chlorpyrifos I + TX, chlorpyrifos II + TX, chloranil + TX, cis-resmethrin + TX, cis-resmethrin + TX, cypermethrin + TX, chloranil + TX, chloranil + TX, copper acetyl arsenite + TX, copper arsenate + TX, copper oleate + TX, coumaphos + TX, chloranil + TX, crotamiton + TX, baclofos + TX, clofosinate + TX, ice crystal Stone + TX, CS708 + TX, benzonitrile + TX, cypermethrin + TX, fruit insect + TX, cypermethrin + TX, cyfluthrin + TX, trichlorfon + TX, cypermethrin + TX, cypermethrin + TX, cypromethrin + TX, cypromazine + TX, d-limonene + TX, d-tetramethrin + TX, DAEP + TX, dazomethane + TX, DDT + TX, decarbofuran + TX, cypermethrin + TX, tianlephos + TX, tianlephos-O + TX, tianlephos-S + TX, endophos-methyl + TX, endophos-O + TX, endophos-O-methyl + TX, endophos-S + TX, endophos-S-methyl + TX, endophos S-methyl sulfone + TX, dithiocarb + TX, chlormethin + TX, diamidophos + TX, diazinon + TX, isochlorophos + TX, dimethophos + TX, dichlorvos + TX, dicliphos + TX, dicresyl + TX, dicrotophos + TX, dichlorvos + TX, dichlorvos + TX, dichlorvos + TX, dieldrin + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, diflubenzuron + TX, dihydroxypropyltheophylline (dilor) + TX, tetrafluthrin + TX, methylphosphine + TX, dimethoate + TX, dimethoate + TX, pyrethrin + TX, methylchlorfenapyr + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX, dimethoate + TX,Dinotefuran+TX, benzylpyridin+TX, venom+TX, dimethoate+TX, dimethoate+TX, dithiophos+TX, dithiophos+TX, DNOC+TX, doramectin+TX, DSP+TX, ecdysone+TX, EI1642+TX, methoxyavermectin+TX, methoxyavermectin benzoate+TX, EMPC+TX, fenthrin+TX, endosulfan+TX, endophos+TX, endrin+TX, EPBP+TX, EPN+TX, fenvalerate+TX, eprinomectin+TX, cypermethrin+TX, etaphos+TX, ethiofencarb+TX, ethion+TX, ethiprole+TX , methyl thiophos + TX, ethoxyproline + TX, ethyl formate + TX, ethyl-DDD + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, ethoxyproline + TX, ethoprophos + TX, EXD + TX, sulfamethoxam + TX, fenamiphos + TX, anti-mite azole + TX, pyraclostrobin + TX, fenfluramide + TX, fenfluramide + TX, fenthiocarb + TX, fenfluramide + TX, fenthiocarb + TX, fenpyrad + TX, fenthiophos + TX, fenthiocarb + TX, fenpyrad + TX, fenthiophos + TX, fenthion-ethyl + TX, fenvalerate + TX, fipronil + TX, flonicamid + T X、flubencarb [272451-65-7] + TX、flucofuron + TX、flufenac + TX、flucythrinate + TX、diflunisal + TX、flufenamid + TX、flufenuron + TX、trifluthrin + TX、flumethrin + TX、fluvalinate + TX、FMC1137 + TX、fenofos + TX、flufenapyr + TX、flufenapyr hydrochloride + TX、anthiophos + TX、formparanate + TX、butylfenthion + TX、fospyralid + TX、thiathrin + TX、butylthiophos + TX、furox + TX、anthin + TX、γ-cyhalothrin + TX、γ-HCH + TX、biguanide salt + TX、biguanide acetate + TX、GY- 81+TX, benzyl acarb+TX, chlorfenapyr+TX, HCH+TX, HEOD+TX, Feibuda+TX, heptenephos+TX, cypermethrin+TX, hexaflumuron+TX, HHDN+TX, hydrazone+TX, hydrocyanic acid+TX, methoprene+TX, hyquincarb+TX, imidacloprid+TX, imiprolin+TX, indoxacarb+TX, iodomethane+TX, IPSP+TX, chlorfenapyr+TX, carbochlorin+TX, isocarb+TX, isothiocarb+TX, isoprocarb+TX, O-(methoxyaminothiophosphoryl) salicylic acid isopropyl ester+TX, rice blast+TX, isothiophos+TX, oxathiophos+TX, ivermectin+TX,Jasmonate I + TX, Jasmonate 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, lepidomicil + TX, parabromophos + TX, lindane + TX, lirimfos + TX, lufenuron + TX, thiathion + TX, m-isopropylphenyl methylcarbamate + TX, magnesium phosphide + TX, malathion + TX, tebuconazole + TX, azidophos + TX, chlorpyrifos + TX, tetramethylphos + TX, chlorpyrifos + TX, dianphos + TX, mercurous chloride + TX, mesulfenfos + TX, metaflumizone + TX, metamizole + TX, metamizole potassium + TX, metamizole sodium + TX, acarb + TX, methyl parathion + TX, methanesulfonyl fluoride + TX, methamidophos + TX, methiocarb + TX, chlorpyrifos + TX, methomyl + TX, methomyl + TX, mequindox + TX, methylthiothrin + TX, methoxychlor + TX, anthracene + TX, methyl bromide + TX, methyl isothiocyanate + TX, methyl chloroform + TX, dichloromethane + TX, methicillin + TX, cypermethrin + TX,

[0168] +TX, anthracene +TX, cypermethrin +TX, zikwei +TX, mitraming +TX, milbemycin +TX, propylamine fluoride +TX, anticide +TX, monocrotophos +TX, chlorpyrifos +TX, moxifloxacin +TX, moxidectin +TX, naphthyl phosphate +TX, dibromophos +TX, naphthalene +TX, NC-170 +TX, NC-184 +TX, nicotine +TX, nicotine sulfate +TX, fluazifop +TX, nitenpyram +TX, nithiazine +TX, pentamethylenediamine +TX, pentamethylenediamine 1:1 zinc chloride complex +TX, NNI-0101 +TX, NNI-0250 +TX, nornicotine +TX, flubendiamide +TX, fluazifop +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 dithiodipyrophosphate + TX, oleic acid + TX, omethoate + TX, oxamyl + TX, sulfone-methyl + TX, isosulfoxide + TX, sulfone + TX, pp'-DDT + TX, p-dichlorobenzene + TX, parathion + TX, parathion-methyl + TX, flufenuron + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, permethrin + TX, petroleum oil + TX, PH60-38 + TX, fenthion + T X, phenothrin + TX, dapoxetine + TX, phorate + TX, phosalone + TX, thiophos + TX, phosmet + TX, parachlorothion + TX, phosphamidon + TX, phosphine + TX, phoxim + TX, phoxim-methyl + TX, pirimetaphos + TX, pirimetaphos + TX, cypermethrin + TX, cypermethrin-ethyl + TX, cypermethrin-methyl + TX, polychlorodicyclopentadiene isomers + TX, polychloroterpenes + TX, potassium arsenite + TX, potassium thiocyanate + TX, propylthrin + TX, precocious element I + TX, precocious element II + TX, precocious element III + TX, primidophos + TX, profenofos + TX, profluthrin + TX, cypermethrin + TX, cypermethrin +TX, propanil +TX, amine propanil +TX, propoxur +TX, ethiazole +TX, prothiophos +TX, thiophos +TX, protrifenbute +TX, pymetrozine +TX, pyraclostrobin +TX, pyrafluprole +TX, pyrafluprole +TX, pyresmethrin +TX, pyrethrin I +TX, pyrethrin II +TX, pyrethrins +TX, pyrethrin +TX, pyrethrin +TX, pyrimidine +TX, pyrimidine +TX, pyrimidine +TX, pyriproxyfen +TX, quassia extract (quassia) +TX, quinalphos +TX, quinalphos-methyl +TX,Cynophos + TX, quintiofos + TX, R-1492 + TX, rafonilide + TX, resmethrin + TX, rotenone + TX, RU15525 + TX, RU25475 + TX, ryania + TX, lianodine + TX, sabaveratrum + TX, octamethoxam + TX, thiamethoxam + TX, selamectin + TX, SI-0009 + TX, SI-0205 + TX, SI-0404 + TX, SI-0 405+TX, flutosilicate+TX, SN72129+TX, sodium arsenite+TX, sodium cyanide+TX, sodium fluoride+TX, sodium hexafluorosilicate+TX, sodium pentachlorophenol+TX, sodium selenate+TX, sodium thiocyanate+TX, thionylthion+TX, spinosad+TX, spiromesifen+TX, spirotetramat+TX, sulcofuron+TX, sulcofuron-sodium+TX, sulfluramid+TX, thiophos+TX, sulfonyl fluoride+TX, thiopromide+TX X, tars + TX, τ-fluvalinate + TX, thiamethoxam + TX, TDE + TX, fenbufenpyrad + TX, butylpyrimidin + TX, flubenzuron + TX, tefluthrin + TX, bispyribac + TX, TEPP + TX, cypermethrin + TX, terbam + TX, terbuthrin + TX, tetrachloroethane + TX, cypermethrin + TX, θ-cypermethrin + TX, thiacloprid + TX, thiafenox + TX, thiamethoxam + TX, thicrofos+TX, cypermethrin+TX, thiocyclam+TX, thiocyclam hydrogen oxalate+TX, thiodicarb+TX, long-acting carb+TX, methyl thiosulfate+TX, thiosulfuron+TX, thiosultap+TX, thiosultap-sodium+TX, thuringin+TX, tolfenpyrad+TX, tralomethrin+TX, transfluthrin+TX, transpermethrin+TX, cyfluthrin,

[0169] +TX, azomethanil+TX, triazophos+TX, zolylcarb+TX, trichlorfon+TX, trichlormetaphos-3+TX, chlorfenapyr+TX, trichlorpropoxyphos+TX, thiocarb+TX, methoxythiocarb+TX, aphidoxim+TX, vaniliprole+TX, veratridine+TX, veratridine+TX, XMC+TX, cypermethrin+TX, YI-5302+TX, ζ-cypermethrin+TX, zetamethrin+TX, zinc phosphide+TX, zolaprofos, and ZXI8901+TX, cyantraniliprole [736994-63-19]+TX, chlorantraniliprole [500008-45-7]+TX, cyenopyrafenib (cyenopyrafe n) [560121-52-0] + TX, cyfluthrin [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [704886-18-0] + TX, chlorfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX,

[0170] A molluscicide, which is 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, iron 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,

[0171] 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-thioxo-1,3,5-thiadiazinane-3-yl acetic acid+TX, 6-isopentenylaminopurine+TX, Avermectin + TX, acetochlor + TX, cotton bell carb + TX, aldicarb + TX, aldoxycarb + TX, AZ60541 + TX, benclothiaz + TX, benclothiaz + TX, butylpyridaben + TX, cadusafos + TX, carbofuran + TX, carbon disulfide + TX, carbofuran butyryl + TX, chloropicrin + TX, chlorpyrifos + T X, cloethocarb + TX, cytokinins + TX, dazomet + TX, DBCP + TX, DCIP + TX, diamidafos + TX, dichlofenthion + TX, dicliphos + TX, dimethoate + TX, imagotine + TX, imagotine benzoate + TX, eprinomectin + TX, ethoprophos + TX, ethylene dibromide + TX, fenamiphos + TX, tebufenamide + TX, fenpyrad + TX, fosthiazate + TX, fosthietan + TX, furfural + TX, GY-81 + TX, heterophos + TX, iodomethane + TX, isamidofos + TX, isazofos + TX, kinetin

[0172] +TX, furanaminopurine (mecarphon) +TX, methyl mecarphon (mecarphon) +TX, metamex +TX, metamex potassium salt +TX, metamex sodium salt +TX, methyl bromide +TX, methyl isothiocyanate +TX, milbemycinoxime (milbemycinoxime) +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,

[0173] A nitrification inhibitor, which is selected from the group consisting of potassium ethylxanthate and nitrapyrin + TX,

[0174] A plant activator, which is selected from the group consisting of the following substances: acibenzolar+TX, acibenzolar-S-methyl+TX, probenazole and Reynoutria sachalinensis extract+TX,

[0175] A rodenticide, the rodenticide is selected from the group consisting of the following substances: 2-isovaleryl indane-1,3-dione + TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, α-chlorohydrin + TX, aluminum phosphide + TX, antu + TX, arsenic trioxide + TX, barium carbonate + TX, bifenthrin + TX, brodifacoum + TX, brodifacoum + TX, brofenthrin + TX, calcium cyanide + TX, azodipine + TX, chlorofacitin + TX, vitamin D3 + TX, chlorfenapyr + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, Sodium thiamethoxam + TX, vitamin D2 + TX, fludioxaline + TX, fluoroacetamide + TX, thiamethoxam + TX, thiamethoxam hydrochloride + TX, β-HCH + TX, HCH + TX, hydrocyanic acid + TX, methyl iodide + TX, lindane + TX, magnesium phosphide + TX, methyl bromide + TX, thiamethoxam + TX, phosphine + TX, phosphorus + TX, cypermethrin + TX, potassium arsenite + TX, cypermethrin + TX, strychnine + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, thallium sulfate + TX, cypermethrin and zinc phosphide + TX,

[0176] A synergist selected from the group consisting of: 2-(2-butoxyethoxy)ethyl piperonyl ester

[0177] +TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone+TX, farnesol with nerolidol+TX, MB-599+TX, MGK264+TX, piperonyl butoxide+TX, piperone aldehyde (piprotal)+TX, propylisomer+TX, S421+TX, sesamex+TX, sesasmolin and sulfoxide+TX,

[0178] An animal repellent, which is 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, pyridine-4-amine + TX, salam + TX, trimethacarb + TX, zinc naphthenate and ziram + TX,

[0179] A virucide selected from the group consisting of imanin and ribavirin+TX,

[0180] A wound protection agent, which is selected from the group consisting of mercuric oxide + TX, octhilinone and methyl thiophanate + TX,

[0181] and a biologically active compound selected from the group consisting of: azaconazole (60207-31-0] + TX, bifenthrin [70585-36-3] + TX, oxadiazole [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole [106325-08-0] + TX, nitrile Benzazole [114369-43-6] + TX, fluquinazole [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, cyproconazole [125225-28-7] + TX, metconazole [125116-23- 6]+TX, myclobutanil [88671-89-0]+TX, pyroxil [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 e) [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, fluconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimefon [55219-65-3] + TX, triflumuron [99387-89-0] + TX, trichlorfon [131983-72-7] + TX, tricyclam [12771-68-5] + TX, chlorfenapyr [60168-

[0182] 88-9]+TX, fluclofenac [63284-71-9]+TX, bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol [23947-60-6]+TX, dodecacyclic morpholine [1593-77-7]+TX, fenpropidine [67306-00-7]+TX, fenpropimorph [67564-91-4]+TX, spiroxafil [118134-30-8]+TX, tridecamorph [81412-43-3]+TX, cyprodinil [121552-61-2] + TX, pyrimethanil [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [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, oxadone (0 xadixyl)[77732-09-3]+TX、benomyl[17804-35-2]+TX、carbendazim[10605-21-7]+TX、debacarb[62732-91-6]+TX、maisuining[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 [188425-85-6] + TX, carboxin [5234-68-4] + TX, furanilide [24691-80-3] + TX, flutolanil [66332-96-5] + TX, oxadiazine [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX,Thifuranil [130000-40-7] + TX, biguanide salt [108173-90-6] + TX, dodine [2439-10-3] [112-65-2] (free bond) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, doxystrobin [149961-52-4] + TX, oxathiocarb {Proc. BCPC, Int. Congr., Glasgow. 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, methyl doxystrobin [143390-89-0] + TX, Benoxystrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orysastrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, ferram [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, methanamide [9006-42-2] + TX, propineb [12071-83-9] + TX, salamine [137-26-8] + TX, mancozeb [12122-67-7] + TX, ferram [137-30-4]+TX, captafol [2425-06-1]+TX, captan [133-06-2]+TX, benzylfluanid [1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX, tolylfluanid [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 [7758-98-7] + TX, copper oxide [1317-39-1] + TX, mancopper [53988-93-5] + 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,Isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, difop-butyl [101-05-3] + TX, benzathiapyr [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01-2] + T X, chloroneb [2675-77-6] + TX, thiophanate-methyl [1897-45-6] + TX, cyfluthrin [180409-60-3] + TX, cymoxanil [57966-95-7] ​​+ TX, dichlone [117-80-6] + TX, diclocymet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, oxadiazine [110488-70-5] + TX, SYP-LI90 (Flumorph),

[0183] [211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX, etridiazole [2593-15-9]+TX, oxathiapiprolin [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、fenacet[126833-17-8]+TX、fosetyl-aluminium[39148-24-8]+TX、hymexazol[10004-44-1]+TX、propineb[140923-17-7]+TX、IKF-916(Cyazofamid)[120116-88-3]+TX 、kasugamycin [6980-18-3] + TX、methasulfocarb [66952-49-6] + TX、metrafenone [220899-03-6] + TX、pencycuron [66063-05-6] + TX、phthalide [27355-22-2] + TX、polyoxins [11113-80-7] + TX、probenazole [27605-76-1] + TX、propamocarb [25606-41-1] + TX、proquinazid [189278-12-4] + TX, pyroquilon [57369-32-1] + TX, quinoxyfen [124495-18-7] + TX, pentachloronitrobenzene [82-68-8] + TX, sulfur [7704-34-9] + TX, thiazolamide [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, quinazoline [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-bridged methylene-naphthalene-5-yl)-amide (in W 02007 / 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-[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+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 of which are in WO2010 / 1237 91, WO2008 / 013925, WO2008 / 013622 and WO2011 / 051243, page 20) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3', 4', 5'-trifluoro-biphenyl-2-yl)-amide (disclosed in WO2006 / 087343) + TX, and 1-methyl-2-(2,4,5-trichloro-thiophen-3-yl)-ethyl] + TX.

[0184] References in square brackets after the active ingredient, such as [3878-19-1], refer to the registration number of the Chemical Abstracts. The mixing pairs described above are known. For example, they are included in "The Pesticide Manual" [The Pesticide Manual-Global Overview; 13th Edition; Editor: CDS Tom Lin; The British Crop Protection Council (The Pesticide Manual-A World Compendium; Thirteenth Edition; Editor: CDS Tom Lin; The British Crop Protection Council), or in the "Compendium of Pesticide Common Names".

[0185] Most of the active ingredients mentioned above are referred to above by a so-called "common name", a related "ISO common name" or, in individual cases, another "common name". If its 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.

[0186] The mass ratio of any two ingredients in each combination is selected to give the desired, e.g., 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 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, ratios by mass and, on the other hand, molar ratios.

[0196] Examples of methods of application of the compounds and compositions thereof of the present invention, i.e. methods of controlling pests / fungi in agriculture, are spraying, atomizing, dusting, brushing, seed dressing, broadcasting or pouring - they are selected to suit the intended purpose under the prevailing circumstances.

[0197] A preferred method of application in agriculture is application to the leaves of the plants (foliar application), it being possible to choose the frequency and rate of application to correspond to 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 drenching) or by applying the compound in solid form to the soil in the form of granules (soil application). In the case of rice plants, such granules can be metered into flooded paddy fields.

[0198] The application rate per hectare is generally 1 g to 2000 g of active ingredient per hectare, especially 10 g / ha to 1000 g / ha, preferably 10 g / ha to 600 g / ha, such as 50 g / ha to 300 g / ha.

[0199] These compounds of the present invention and compositions thereof are also suitable for the protection of plant propagation materials (for example seeds, such as fruits, tubers or grains, or nursery plants) against the harmful organisms of the above type. The propagation material can be treated with the compound before planting, and for example seeds can be treated before sowing. Alternatively, the compound can be applied to seed grains (coating), which is achieved by dipping the grains into a liquid composition or by applying a solid composition layer. When the propagation material is planted in the application site, it is also possible, for example, to apply these compositions to the seed furrow during drilling. These treatment methods for plant propagation materials and the plant propagation materials thus treated are other themes of the present invention. Typically, the treatment rate will depend on the plant to be controlled and the harmful organism / fungus, usually between 1 gram to 200 grams per 100kg seeds, preferably between 5 grams to 150 grams per 100kg seeds, such as between 10 grams to 100 grams per 100kg seeds.

[0200] The term seed includes all kinds of seeds and plant propagules including but not limited to true seeds, seed pieces, suckers, kernels, corms, fruits, tubers, grains, rhizomes, cuttings, cuttings and the like and in a preferred embodiment refers to true seeds.

[0201] 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, I', I" or I"'. The term "coated 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 a compound of formula I, I', I" or I"' adhered thereto. In addition, a composition comprising plant propagation material treated with a compound of formula I, I', I" or I"' is thereby obtainable.

[0202] 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 the compound of formula I, I', I" or I"' can be achieved by any known method, such as spraying or by dusting before sowing or during sowing / planting of these seeds.

[0203] Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, corn or sorghum; beets, such as sugar 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; melon crops, such as pumpkins, cucumbers or melons; Fibrous 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, sugar cane, tea, pepper, grapevines, hops, the Plantaginaceae family, rubber plants and ornamental plants (e.g., flowers and lawn plants or turf).

[0204] In one embodiment, the plant is selected from the group consisting of cereals, corn, soybeans, rice, sugar cane, vegetables and oil plants.

[0205] 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 those of the genus Bacillus.

[0206] 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, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), 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 inhibitors, serine protease inhibitors, selenotoxin ... Protease inhibitors, potato storage proteins (patatin), cysteine ​​protease inhibitors, papain inhibitors; ribosome inactivating proteins (RIPs), such as ricin, corn-RIP, abrin, luffa seed toxin, saponin or dioscorea toxin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, 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.

[0207] In the context of the present invention, delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vips), such as Vip1, Vip2, Vip3 or Vip3A, should be understood to obviously also include mixed toxins, truncated toxins and modified toxins. Mixed toxins are produced by new combinations and recombination of 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 naturally occurring toxins are replaced. In this amino acid replacement, it is preferred that non-naturally occurring protease recognition sequences are 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).

[0208] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878 and WO03 / 052073.

[0209] Methods for preparing such transgenic plants are known to the person 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.

[0210] 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 especially commonly found in beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

[0211] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some are commercially available.

[0212] Typically, the compounds of the invention are used in the form of a composition (eg, formulation) comprising a carrier. The compounds and compositions of the present invention can be used in different forms, for example, aerosol sprays, 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-producing 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.

[0213] A formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation adjuvants which may be solid or liquid adjuvants, for example, 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 regulators, surfactants, binders and / or tackifiers. The composition may further comprise a fertilizer, micronutrient donor or other preparation that influences plant growth, and includes a combination comprising a compound of the invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0214] The invention therefore also makes available a composition comprising a compound according to the invention together with an agronomically acceptable carrier and optionally one or more customary formulation auxiliaries.

[0215] These compositions are prepared in a manner known per se, for example by grinding, sieving and / or squeezing the solid compound of the invention in the absence of an auxiliary agent and for example by intimately mixing and / or grinding the compound of the invention with one or more auxiliary agents in the presence of at least one auxiliary agent. In the case of solid compounds of the invention, the grinding / grinding of the compound is to ensure a specific particle size. The methods for preparing these compositions and the use of the compounds of the invention for preparing these compositions are also a subject of the present invention.

[0216] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, diluted 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.

[0217] Examples of suitable liquid carriers are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably C 8 To C 12 alkylbenzene parts of the present invention, such as xylene mixtures, alkylated naphthalene or tetralin, 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, unepoxidized or epoxidized vegetable oils, such as unepoxidized or epoxidized rapeseed oil, castor oil, coconut oil or soybean oil and silicone oils.

[0218] Examples of solid carriers for example dusts and dispersible powders are generally ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. In order to improve the physical properties, it is also possible to add highly dispersed silica or highly dispersed absorbent polymers. Suitable granular adsorptive carriers for granules are porous types, such as pumice, gravel, sepiolite or bentonite, and suitable non-absorptive carrier materials are calcite or sand. In addition, a large number of granulated materials of inorganic or organic natural substances can be used, in particular dolomite or crushed plant residues.

[0219] 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 which are conventionally used in the field of formulations and which are suitable according to the invention are described in the relevant literature.

[0220] Suitable nonionic surfactants are, in particular, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, polyglycol ether derivatives of saturated or unsaturated fatty acids or polyglycol 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 part 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 ether, castor oil polyglycol 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.

[0221] These cationic surfactants are in particular quaternary ammonium salts which usually have at least one alkyl residue (from about 8 to about 22 C 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, methyl sulfates or ethyl sulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.

[0222] 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 C atoms, such as the sodium or potassium salts of oleic acid or stearic acid or of natural fatty acid mixtures (obtainable, for example, from coconut oil or tall oil); mention must also be made of the fatty acid methyltaurine. More commonly used, however, are synthetic surfactants, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates. Typically, these fatty sulfonates and fatty sulfates are alkali metal salts, alkaline earth metal salts or (substituted or unsubstituted) ammonium salts and they typically have alkyl residues having from about 8 to about 22 C atoms, alkyl also being understood as the alkyl part including the acyl residue; examples which may be mentioned are the sodium or calcium salts of ligninsulfonic acid, the sodium or calcium salts of dodecyl 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 2 sulfonyl groups and fatty acid residues of about 8 to about 22 C 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.

[0223] Typically, these compositions contain 0.1% to 99% (especially 0.1% to 95%) of a compound according to the invention and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier, it being possible in principle that 0% to 25% (especially 0.1% to 20%) of the composition are surfactants (% in each case denotes percentage by weight). For commercial purposes, however, concentrated compositions are generally preferred, the end user in principle using dilute compositions with significantly lower concentrations of active ingredients.

[0224] Examples of suitable formulation types for the tank mix composition are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0225] As to the nature of the formulations, the methods according to the invention, such as foliage, drenching, spraying, atomizing, dusting, spreading, applying or pouring, may be chosen according to the intended purposes and the prevailing circumstances.

[0226] Such tank-mix compositions are generally prepared by diluting one or more premix compositions containing different pesticides and optionally additional adjuvants with a solvent (eg, water).

[0227] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, extenders, binders or fertilizers.

[0228] 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 adjuvants may be a surfactant, in an amount of 0 to 20%, especially 0.1% to 15%, based on the tank-mix formulation.

[0229] Typically, premix formulations for foliar application comprise 0.1% to 99.9%, especially 1% to 95%, of the desired ingredients, and 99.9% to 0.1%, especially 99% to 5%, of solid or liquid adjuvants (including, for example, a solvent such as water), wherein the adjuvants may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0230] 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), wherein the adjuvants may be a surfactant, in an amount of 0 to 40%, especially 0.5 to 30%, based on the tank-mix formulation.

[0231] 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), wherein the adjuvants may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the tank mix formulation.

[0232] While commercial products are preferably formulated as concentrates (eg, pre-mix compositions (formulations)), end users typically employ diluted formulations (eg, tank mix compositions).

[0233] 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 methods, rotostatic seed processors, and drum applicators. Other methods, such as spouted beds, 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.

[0234] 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.

[0235] 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 materials, wherein the composition for protecting plant propagation materials further comprises a colorant. This composition or mixture for protecting plant propagation materials may also include at least one copolymer from water-soluble and water-dispersible film-forming polymers that improve the attachment of the active ingredients to the treated plant propagation materials, the polymers generally having an average molecular weight of at least 10,000 to about 100,000.

[0236] 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.

[0237] 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 to achieve the biological effect, such as within a few hours or a few 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.

[0238] In this case, in the present invention, the components of the combination are applied simultaneously, they can be applied as a composition containing the combination, in which case (A) the compound of formula I, I', I" or I'" and one or more components of the combination can be obtained from a separate formulation source and mixed together (called 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 components of the combination can be used as a separate formulation mixture source (called a premix, i.e., a mixture, a concentrate or a formulated product).

[0239] In one embodiment, independently of other embodiments, a compound according to the invention is administered as a combination. Therefore, 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.

[0240] 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 that may be mentioned are: advantageous behavior during formulation and / or application (e.g. when grinding, sieving, emulsifying, dissolving or dispersing); increased storage stability, improved light stability; more favorable degradability; improved toxicological and / or ecotoxicological behavior; or other advantages familiar to those skilled in the art.

[0241] The compounds of the invention are preferably used as a nematicide in agriculture.

[0242] These compounds of the invention may also find application in other fields, such as one or more of the following: protection of stored goods and storerooms, protection of raw materials (such as wood, textiles), floor coverings and buildings, and in hygiene management - especially protection of humans, livestock and productive livestock against harmful organisms. The invention thus also makes available pesticidal compositions for such uses and methods for the same. The compositions for use in specific uses will need to be modified, and the skilled person will be able to make available such compositions for any specific use.

[0243] 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.

[0244] The compositions according to the invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floors and buildings, etc. from insect attack. The compositions according to the invention can be used, for example, against the following pests: beetles, such as the 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 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 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 Da's Australian termite, the Nevada termite and the Formosan termite, and wingless insects such as silverfish.

[0245] Methods for applying a compound or a combination thereof to stored goods, storerooms, raw materials (such as wood panels and textiles), floor coverings and buildings, and in hygiene management are known in the art.

[0246] 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, arachnid species 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 effective amount of a compound of formula I, I', I" or I'"'.

[0247] The above method is particularly useful for controlling and preventing infestations and infections caused by worms, nematodes, mites and endo- and ectoparasites in warm-blooded animals such as cattle, sheep, pigs, camels, deer, horses, poultry, fish, rabbits, goats, minks, foxes, chinchillas, dogs and cats, as well as humans.

[0248] In the context of controlling and preventing infestations and infections in warm-blooded animals, the compounds of the invention are particularly useful for the control of helminths and nematodes. Examples of helminths are members of the class Trematoda, commonly referred to as trematodes or flatworms, particularly members of the genera Fasciola, Pseudomonas, Homodiscus, Diplostomum, Broaddiscus, Ophisthorchis, Fasciola, Echinostoma, and Paragonimus. Nematodes that may be controlled by compounds of formula I, I', I" or I"' include Haemonchus, Osternae, Cooperia, Oesphagastomu, Neck nematodes, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaris, and the like.

[0249] The compounds of the present invention can also control infestations of arthropods that are parasitic in the body, such as the larvae of the skin flies and the gastric flies. In addition, mites and arthropod ectoparasitic infestations in warm-blooded animals and fishes include biting lice, sucking lice, skin flies, biting flies, muscoid flies, flies, myiasitic fly larvae, gnats, mosquitoes, fleas, mites, ticks, nasal bots, sheep tick flies and chiggers can be controlled, prevented or eliminated by these compounds of the present invention. Biting lice include members of the order Trichophaga such as the bovine hair lice, the dog hair lice and the sheep wool lice (Damilina ovis). Sucking lice include members of the order Pseudoptera such as the bovine blood lice, the suid blood lice, the bovine jaw lice and the buffalo blind lice. Biting flies include members of the genus Nigrocera. Ticks include the genus Boophila, the genus Rhipicephala, the genus Ixodes, the genus Hyalomma, the genus Amblyomma and the genus Rhizoctonia. The compounds of the present invention may also be used to control mites that parasitize warm-blooded mammals and poultry, including mites of the orders Acarina and Parasiticus.

[0250] For oral administration to warm-blooded animals, the compounds of the present invention can be formulated into animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, 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 about 0.01 mg / kg to 100 g / kg of the compound of the present invention per day.

[0251] 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 to animals percutaneously. For parenteral administration, the selected dosage form should provide the animals with a compound of the present invention of about 0.01 mg / kg to 100 mg / kg of animal body weight every day.

[0252] The compounds of the present invention can also be topically applied 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.

[0253] 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.

[0254] The parasiticidal compositions of the present invention include a parasiticidal effective amount of a compound of the present invention or a combination thereof mixed with one or more physiologically tolerable inert solid or liquid carriers, which are known in veterinary practice for oral, percutaneous and topical administration. Such compositions may further include a variety of additives, such as stabilizers, defoamers, viscosity regulators, adhesives and tackifiers, while commercial products will preferably be formulated as concentrates, and end users will generally use diluted formulations.

[0255] 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 and candidiasis or diseases caused by Aspergillus, such as Aspergillus fumigatus.

[0256] In one embodiment, independent of any other embodiment, the compound of formula I, I', I", or I'" is an anthelmintic compound.

[0257] 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

[0258] The following examples are used to illustrate the present invention and should not be considered to limit the present invention in any way. The scope of the rights required to be protected by the present invention is described by the claims.

[0259] In view of the economic efficiency and diversity of the compounds, we preferably synthesized some compounds, and among the many synthesized compounds, some are selected and listed in the following Table 1. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustrating the present invention, but not for limiting the present invention. For those skilled in the art, this should not be understood as the scope of the above subject matter of the present invention is limited to the following compounds.

[0260] Table 1 Compound structures

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272] Table 2 Compounds 1 H NMR

[0273]

[0274]

[0275]

[0276] 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' And in Table A, the entries under the "Serial Number" column heading are sequentially described as 1 (cis) to 148 (cis). For example, 1 (cis) corresponds to the compound in Table 1 where Compound 1 is a cis form.

[0277] Table B is constructed in the same manner as Table 1 above, except that the compounds of formula I are replaced with the compounds of formula I having a chiral center. In Table B, the entries under the "Serial Number" column heading are sequentially described as 1(RR)-148(RR). For example, 1(RR) corresponds to the compound 1 in Table 1 in which both positions 1 and 2 on the four-membered ring are in R configuration.

[0278] 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 And in Table C, the entries under the "Serial Number" column heading are sequentially described as 1(SS)-148(SS). For example, 1(SS) corresponds to the compound 1 in Table 1 in which both positions 1 and 2 on the four-membered ring are in S configuration.

[0279] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be purchased from the market or can be prepared by methods known in the literature or as shown in the detailed description. It will be appreciated 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 raw materials and conditions in the synthetic route have been described below, it can be easily replaced with other similar raw materials and conditions, and these modifications or variations of the preparation method of the present invention such as various isomers of the compound are included within the scope of the present invention. In addition, the preparation method described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, appropriate groups are protected during the reaction, etc.

[0280] The method examples provided below are used to promote further understanding of the preparation method of the present invention. The specific substances, types and conditions used are determined to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the following table can be purchased commercially or can be easily prepared by a person of ordinary skill in the art.

[0281] Examples of representative compounds are as follows. The synthesis methods of other compounds are similar and will not be described in detail here.

[0282] 1. Synthesis of Compound 8 (cis)

[0283] (1) 8-1 (10 g, 1 eq) was dissolved in 300 ml of DMF at room temperature, and potassium carbonate (3 eq) and 4-chloropyrazole (1.1 eq) were added in sequence. After the addition was completed, 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 water and EA were added to the system for extraction. The organic phase was washed three times with saturated brine, and the organic phase was concentrated and slurried with EA to obtain 8-2 (6.0 g, 40%).

[0284]

[0285] (2) (3-Bromopropyl)triphenylphosphonium bromide (1.1 eq) was added to anhydrous THF (80 ml), and potassium tert-butoxide (3 eq) was added in batches to give a yellow suspension. The mixture was heated to reflux for 30 min and 8-2 (6.0 g, 1 eq) was added to give a yellow-brown suspension. The reaction mixture was stirred and heated to reflux for 4 h. The reaction was then cooled to room temperature and filtered through a celite pad. The solvent was removed in vacuo and the resulting crude material was subjected to flash chromatography using petroleum ether as eluent to give 8-3 (2.6 g, 39%).

[0286]

[0287] (3) To a solution of 8-3 (2.5 g, 1 eq) in DCM (50 ml) was added m-chloroperbenzoic acid (1.1 eq) in portions at 0° C. After stirring at 0° C. for 16 h, the reaction mixture was directly concentrated and purified by silica gel column chromatography to give 8-4 (1.5 g, 55%).

[0288]

[0289] (4) 8-4 (1.5 g, 1 eq) was dissolved in 30 mL of tetrahydrofuran, and 2-methyl-2-propanesulfenamide (3 eq) and titanium tetraethoxide (2 eq) were added in sequence. The mixture was heated to 70 ° C. and stirred for 5 h. When the reaction was completed, water was added to quench the reaction. The insoluble matter was filtered off with diatomaceous earth. 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 8-5 (1.6 g, 80%).

[0290]

[0291] (5) 8-5 (1.6 g, 1 eq) was dissolved in 30 mL MeOH. Sodium borohydride (2 eq) was added in batches under ice bath conditions. The mixture was stirred for 1 h in an ice bath. The reaction was completed at the mid-control stage. The solvent was removed by concentration. The mixture was extracted with water and ethyl acetate for 3 times. The organic phases were combined, dried and concentrated to obtain 8-6 (1.4 g, 88%).

[0292]

[0293] (6) 8-6 (1.4 g, 1 eq) was dissolved in 20 mL of hydrochloric acid in 1,4-dioxane and stirred at room temperature for 30 min. After the reaction was completed, the reaction was directly concentrated and the oil pump was used to obtain the hydrochloride salt of 8-7 (1.0 g, crude product).

[0294]

[0295] (7) 8-7 (1.0 g, 1 eq) was dissolved in 20 mL of acetone: water = 2:1, and Fmoc-OSu (1 eq) and sodium bicarbonate (1.1 eq) were added in turn under ice bath conditions. The mixture was warmed to room temperature and stirred overnight. When the reaction was completed, 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 8-8 (0.45 g, 26%).

[0296]

[0297] (8) 8-8 (0.45 g, 1 eq) was dissolved in 10 mL of piperidine in DMF (20%) and stirred at room temperature for 1 to 2 hours. After the reaction was completed, water and EA were added for extraction three times. The organic phases were combined and washed three times with saturated brine. The organic phase was dried to obtain 8-9 (0.5 g, crude product).

[0298]

[0299] (9) 8-9 (100 mg, 1 eq) was dissolved in 10 mL DCM. At room temperature, 8-10 (1 eq), triethylamine (3 eq), and HATU (1.5 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 8 (cis) (40 mg, 48%).

[0300]

[0301] Biological activity evaluation (nematode 96-well plate bioassay):

[0302] (1) Preparation of test agents

[0303] Accurately weigh the test agent, dissolve it in DMSO to prepare a stock solution, and dilute it into different concentration gradient solutions.

[0304] (2) Isolation of target nematodes (root-knot nematodes incognita)

[0305] When egg masses grow on the root nodes, use tweezers to pick out the egg masses in the root nodes under a dissecting microscope and place them in clean water. Soak them in 0.25% sodium hypochlorite aqueous solution for about 1 minute. After washing and sieving with a 500-mesh sieve, place them in a 90mm culture dish containing an appropriate amount of tap water, put them in a sieving device, and culture them in a 28°C incubator for 3 days. The egg masses will then hatch into second-instar larvae.

[0306] (3) Chemical treatment

[0307] Add 100 μL of the prepared test agent and nematode suspension to the 96-well culture plate, cover to prevent evaporation, and place in a 28°C incubator. Set up a water control and a drug control for the test; if a solvent is used, set up a solvent control.

[0308] (4) Cultivation and observation

[0309] The nematodes treated with the drug were cultured under normal conditions, and the mortality of the nematodes was tested for 48 hours and 72 hours: mortality (%) = (number of dead worms / number of worms tested) * 100. The representative test results are shown in Table 3.

[0310] Table 3 Insecticidal test results

[0311]

[0312]

[0313] Note: N means no data, reference compound A:

[0314] At the same time, through many tests, it was found that many of the compounds and compositions of the present invention have good control activity against different types of nematodes, etc., have the characteristics of broad spectrum, high efficiency, strong systemicity, etc., can effectively control harmful organisms 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, Q represents an aryl group or a heterocyclic group; Y represents halogen; X represents halogen, nitro, cyano, thiocyano, hydroxyl, mercapto, 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; R1, R2, R3, R4, and R5 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 or phenoxy substituted by at least one group selected from the following: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy; The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclyl", "non-aromatic 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: X represents halogen, nitro, cyano, thiocyano, hydroxyl, mercapto, 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; R1, R2, R3, R4, and R5 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 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", "non-aromatic 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: X represents halogen, nitro, cyano, thiocyano, 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; R1, R2, R3, R4, and R5 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 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", "non-aromatic 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.

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: wherein R1, R2, R3, R4, R5, X, Y, Q are as defined above, 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: The compound represented by the general formula II is reacted with the compound represented by the general formula III or its amine salt (such as hydrochloride) to obtain the compound represented by the general formula I, and the reaction equation is as follows: Wherein, M represents OH or halogen, and the substituents R1, R2, R3, R4, R5, X, Y and Q are defined as any one of claims 1 to 6; Preferably, the reaction is carried out in the presence of a solvent, more preferably, a condensing agent and / or a base is added during the reaction, and further preferably, the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate; the base is selected from at least one of an inorganic base or an organic base, and the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU.

8. A composition for killing pests and / or fungi (especially nematodes), characterized in that: A composition comprising a biologically effective amount of at least one of the 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 (especially nematodes) 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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