Substituted arylamide compound or salt thereof, method for preparing same, composition comprising same, and use of same

Abstract

The present invention relates to the technical field of pesticides, and in particular to a substituted arylamide compound or salt thereof, a composition comprising same, and a use of same. The compound is as shown in general formula I, wherein M represents CR9 or N; W represents O or S; R1, R2, R3, R4, R5, R6, R6, R7, R8, and R9 each independently represent hydrogen, halogen, alkyl, or the like; R11, R12, R13, R14, and R15 each independently represent hydrogen, halogen, alkyl, or the like; and R16 represents halogen, alkyl, alkenyl, alkynyl, or the like. The compound has an excellent control effect on Tetranychus truncatus, Tetranychus cinnabarinus, and the like.

Description

Substituted arylamide compound or salt thereof, and preparation method, composition and use thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a substituted arylamide compound or salt thereof, and a preparation method, composition and use thereof. BACKGROUND

[0002] In crop production in the fields of agriculture and horticulture, damage caused by pests remains serious, and due to the generation of pests having resistance to existing agents and the like, it is desired to develop novel agricultural and horticultural insecticides and acaricides. Due to the increase in the number of elderly agricultural workers, various labor-saving application methods are required, and it is also required to create agricultural and horticultural insecticides and acaricides having properties suitable for the application methods. SUMMARY

[0003] The present application provides a substituted arylamide compound or salt thereof, and a preparation method, composition and use thereof, the compound having excellent control effects on Tetranychus truncatus, Tetranychus cinnabarinus and the like.

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

[0005] A substituted arylamide compound or salt thereof as shown in general formula I:

[0006] wherein M represents CR9 or N;

[0007] W represents O or S;

[0008] R1, R2, R3, R4, R5, R6, R6, R7, R8, R9 respectively independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyano, nitro, -OR 21 , -S(O) m R 21 , -N(R 22 )2, -(CO)R 21 , -(CO)OR 21 , -O(CO)R 21 , -(CO)N(R 22 )2, cycloalkyl, cycloalkenyl, aryl or heterocyclic group;

[0009] or R1 and R2, R3 and R4, R5 and R6 or R7 and R8 together form =O;

[0010] or R3 and R7, R1 and R5, R3 and R5 or R1 and R7 together form C1-C6 alkylene;

[0011] R 11 , R12 , R 13 , R 14 , R 15 respectively independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -OR 21 , -S(O) m R 21 , -OS(O) m R 21 , -S(O) m N(R 22 )2, -N(R 22 )2, -(CO)R 21 , -(CO)OR 21 , -O(CO)R 21 , -(CO)N(R 22 )2, -(CS)N(R 22 )2, -NR 22 (CO)R 21 , -NR 22 SO2R 21 , cycloalkyl, cycloalkenyl, aryl or heterocyclyl, said alkyl, alkenyl or alkynyl being optionally substituted by at least one radical selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) m R 21 or -N(R 22 )2;

[0012] R 16 represents halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -OR 21 , -S(O) m R 21 , -OS(O) m R 21 , -S(O) m N(R 22 )2, -N(R 22 )2, -(CO)R 21 , -(CO)OR 21 , -O(CO)R 21 , -(CO)N(R 22 )2, -(CS)N(R 22 )2, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, said alkyl, alkenyl or alkynyl being optionally substituted by at least one radical selected from halogen, cyano, trialkylsilyl, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) m R21 or -N(R 22 )2, wherein at least one of the groups is substituted;

[0013] R 22 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -alkylene-(CO)OR 21 , -(SO2)R 21 , -(SO2)OR 21 , -alkylene-(SO2)R 21 , -(CO)N(R 21 )2, or -(SO2)N(R 26 )2;

[0014] R 21 , R 23 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, or heterocyclyl, wherein the alkyl, alkenyl, or alkynyl is optionally substituted with at least one group selected from halogen, cyano, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -OR 27 , -SR 27 , -O(CO)R 27 , -(CO)R 27 , -(CO)N(R 27 )2, -(CO)OR 27 , or -O(CO)OR 27 ;

[0015] R 24 , R 25 each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl; or CR 24 R 25 together form an unsubstituted or substituted cyclic structure;

[0016] R 26 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl;

[0017] R 27represents independently for each occurrence hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl or phenoxy substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy;

[0018] the aforementioned cycloalkyl, cycloalkenyl, heterocyclyl or aryl group is optionally substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halo-cycloalkyl, cycloalkyl substituted by alkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl which are unsubstituted or substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy, -OR 10 , -O(CO)OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 , -(SO2)R 10 , -N(R 10 )2, -alkylene-OR 10 , -alkylene-SR 10 , -alkylene-(CO)R 10 , -alkylene-(CO)OR 10 , -alkylene-(CO)N(R 10 )2, -alkylene-(CS)N(R 10 )2, -alkylene-(SO)R 10 , -alkylene-(SO2)R 10 , -alkylene-N(R 10 )2, -O-alkylene-(CO)OR 10 , -haloalkylene-OR 10 , -haloalkylene-SR 10 , -haloalkylene-(CO)R 10 , -haloalkylene-(CO)OR 10 , -haloalkylene-(CO)N(R 10 )2, -haloalkylene-(CS)N(R 10 )2, -haloalkylene-(SO)R 10, -haloalkylene-(SO2)R 10 , -haloalkylene-N(R 10 )2or -O-haloalkylene-(CO)OR 10 ; or two adjacent carbon atoms of the ring form a fused ring with -OCH2CH2-, -CH2CH2CH2- or -OCH2O- which is unsubstituted or substituted with at least one group selected from halogen or -(CO)OR 10 ;

[0019] m represents 0, 1 or 2;

[0020] R 10 are each independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, cycloalkylalkyl, aryl, heterocyclyl, or aryl or heterocyclyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0021] In one embodiment, R1, R2, R3, R4, R5, R6, R6, R7, R8, R9 are each independently hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, cyano, nitro, -OR 21 , -S(O) m R 21 , -N(R 22 )2, -(CO)R 21 , -(CO)OR 21 , -O(CO)R 21 , -(CO)N(R 22 )2, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclyl;

[0022] or R1and R2, R3and R4, R5and R6or R7and R8together form =O;

[0023] or R3and R7, R1and R5, R3and R5or R1and R7together form C1-C6 alkylene;

[0024] R 11 , R 12 , R 13 , R 14 , R 15 are each independently hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, -OR 21 , -S(O)m R 21 、-OS(O) m R 21 、-S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 、-(CO)OR 21 、-O(CO)R 21 、-(CO)N(R 22 )2、-(CS)N(R 22 )2、-NR 22 (CO)R 21 、-NR 22 SO2R 21 、 C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted with at least one radical chosen from halogen, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) m R 21 or -N(R 22 )2;

[0025] R 16 represents halogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, cyano, nitro, -OR 21 , -S(O) m R 21 , -OS(O) m R 21 , -S(O) m N(R 22 )2, -N(R 22 )2, -(CO)R 21 , -(CO)OR 21 , -O(CO)R 21 , -(CO)N(R 22 )2, -(CS)N(R 22 )2, C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted with at least one radical chosen from halogen, cyano, tri(C1-C8)alkylsilyl, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) m R 21 or -N(R22 )2independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl, heterocyclyl, -OR

[0026] R 22 independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(C1-C8alkylene)-(CO)OR 21 , -(SO2)R 21 , -(SO2)OR 21 , -(C1-C8alkylene)-(SO2)R 21 , -(CO)N(R 21 )2or -(SO2)N(R 26 )2;

[0027] R 21 , R 23 independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl, wherein said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl, heterocyclyl, -OR 27 , -SR 27 , -O(CO)R 27 , -(CO)R 27 , -(CO)N(R 27 )2, -(CO)OR 27 or -O(CO)OR 27 ;

[0028] R 24 , R 25 independently represents hydrogen, halogen, C1-C8alkoxy, C1-C8alkoxyC1-C8alkyl, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl; or CR 24 R 25 together form a 5- to 8-membered carbocyclic or oxygen-, sulfur- or nitrogen-containing heterocyclic ring; said "5- to 8-membered carbocyclic or oxygen-, sulfur- or nitrogen-containing heterocyclic ring" is unsubstituted or substituted with at least one group selected from oxo, C1-C8alkyl or C1-C8haloalkyl;

[0029] R 26 each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8alkoxy, C1-C8alkylsulfonyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl or C3-C8cycloalkenylC1-C8alkyl;

[0030] R 27 each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogenated C1-C8alkyl, halogenated C2-C8alkenyl, halogenated C2-C8alkynyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, halogenated C1-C8alkyl, C1-C8alkoxy, halogenated C1-C8alkoxy, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl or phenoxy substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, halogenated C1-C8alkyl, C1-C8alkoxy or halogenated C1-C8alkoxy;

[0031] the aforementioned C3-C8cycloalkyl, C3-C8cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, halogenated C1-C8alkyl, halogenated C2-C8alkenyl, halogenated C2-C8alkynyl, C3-C8cycloalkyl, halogenated C3-C8cycloalkyl, C3-C8cycloalkyl substituted by C1-C8alkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkylC2-C8alkenyl, C3-C8cycloalkylC2-C8alkynyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl unsubstituted or substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, halogenated C1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or halogenated C1-C8alkoxy, -OR 10 , -O(CO)OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 , -(SO2)R 10 , -N(R 10 )2, -(C1-C8alkylene)-OR 10 , -(C1-C8alkylene)-SR 10-(C1-C8alkylene)-(CO)R 10 -(C1-C8alkylene)-(CO)OR 10 -(C1-C8alkylene)-(CO)N(R 10 )2, -(C1-C8alkylene)-(CS)N(R 10 )2, -(C1-C8alkylene)-(SO)R 10 , -(C1-C8alkylene)-(SO2)R 10 , -(C1-C8alkylene)-N(R 10 )2, -O-(C1-C8alkylene)-(CO)OR 10 , -(haloC1-C8alkylene)-OR 10 , -(haloC1-C8alkylene)-SR 10 , -(haloC1-C8alkylene)-(CO)R 10 , -(haloC1-C8alkylene)-(CO)OR 10 , -(haloC1-C8alkylene)-(CO)N(R 10 )2, -(haloC1-C8alkylene)-(CS)N(R 10 )2, -(haloC1-C8alkylene)-(SO)R 10 , -(haloC1-C8alkylene)-(SO2)R 10 , -(haloC1-C8alkylene)-N(R 10 )2or -O-(haloC1-C8alkylene)-(CO)OR 10 ; or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2-, -CH2CH2CH2- or -OCH2O- which are unsubstituted or substituted with at least one group selected from halogen or -(CO)OR 10 ;

[0032] m represents 0, 1 or 2;

[0033] R 10 are each independently hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, haloC3-C8cycloalkyl, C3-C8cycloalkyl substituted with C1-C8alkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, or aryl or heterocyclyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy.

[0034] In another specific embodiment, R1, R2, R3, R4, R5, R6, R7, R8, and R9 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, cyano, nitro, and -OR, respectively. 21 -S(O) m R 21 -N(R) 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 2. C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups;

[0035] Or R1 and R2, R3 and R4, R5 and R6, or R7 and R8 together form =O;

[0036] Alternatively, R3 and R7, R1 and R5, R3 and R5, or R1 and R7 together can form C1-C6 alkylene groups;

[0037] R 11 R 12 R 13 R 14 R 15 Each of these independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, and -OR. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 )2、-NR 22 (CO)R 21 -NR 22 SO2R 21 , C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic, -OR21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced;

[0038] R 16 Represents halogens, C1-C6 alkyl groups, C2-C6 alkenyl groups, C2-C6 alkynyl groups, cyano groups, nitro groups, and -OR groups. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 2. C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is optionally selected from halogen, cyano, triC1-C6 alkylsilyl, C3-C6 cycloalkyl, aryl, heterocyclic, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced;

[0039] R 22 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic, and -OR. 21 -(CO)R 21 -(CO)OR 21 -(C1-C6 alkylene)-(CO)OR 21 -(SO2)R 21 -(SO2)OR 21 -(C1-C6 alkylene)-(SO2)R 21 -(CO)N(R) 21 )2 or -(SO2)N(R 26 )2;

[0040] R 21 R 23each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl, aryl or heterocyclyl, wherein said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl is optionally substituted with at least one radical selected from the group consisting of halogen, cyano, C3-C6cycloalkyl, C3-C6cycloalkenyl, aryl, heterocyclyl, -OR 27 , -SR 27 , -O(CO)R 27 , -(CO)R 27 , -(CO)N(R 27 )2, -(CO)OR 27 or -O(CO)OR 27 ;

[0041] R 24 , R 25 each independently represents hydrogen, halogen, C1-C6alkoxy, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, aryl, arylC1-C6alkyl, heterocyclyl or heterocyclylC1-C6alkyl; or CR 24 R 25 together form a 5- to 8-membered saturated carbocyclic ring or said 5- to 8-membered saturated carbocyclic ring or is unsubstituted or substituted with at least one radical selected from the group consisting of oxo, C1-C6alkyl or C1-C6haloalkyl;

[0042] R 26 each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, C1-C6alkylsulfonyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl or C3-C6cycloalkenylC1-C6alkyl;

[0043] R 27represents independently from each other hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halogenated C1-C6-alkyl, halogenated C2-C6-alkenyl, halogenated C2-C6-alkynyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C6-alkyl, halogenated C1-C6-alkyl, C1-C6-alkoxy, halogenated C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylsulfonyl or phenoxy substituted by at least one group selected from halogen, cyano, nitro, C1-C6-alkyl, halogenated C1-C6-alkyl, C1-C6-alkoxy or halogenated C1-C6-alkoxy;

[0044] the aforementioned C3-C6-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, halogenated C1-C6-alkyl, halogenated C2-C6-alkenyl, halogenated C2-C6-alkynyl, C3-C6-cycloalkyl, halogenated C3-C6-cycloalkyl, C3-C6-cycloalkyl substituted by C1-C6-alkyl, C3-C6-cycloalkylC1-C6-alkyl, C3-C6-cycloalkylC2-C6-alkenyl, C3-C6-cycloalkylC2-C6-alkynyl, aryl or arylC1-C6-alkyl, heterocyclyl or heterocyclylC1-C6-alkyl unsubstituted or 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, -OR 10 , -O(CO)OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 , -(SO2)R 10 , -N(R 10 )2, -(C1-C6-alkylene)-OR 10 , -(C1-C6-alkylene)-SR 10 , -(C1-C6-alkylene)-(CO)R 10 , -(C1-C6-alkylene)-(CO)OR 10 , -(C1-C6-alkylene)-(CO)N(R 10 )2, -(C1-C6-alkylene)-(CS)N(R 10 )2, -(C1-C6-alkylene)-(SO)R10 -(C1-C6alkylene)-(SO2)R 10 -(C1-C6alkylene)-N(R 10 )2, -O-(C1-C6alkylene)-(CO)OR 10 -(haloC1-C6alkylene)-OR 10 -(haloC1-C6alkylene)-SR 10 -(haloC1-C6alkylene)-(CO)R 10 -(haloC1-C6alkylene)-(CO)OR 10 -(haloC1-C6alkylene)-(CO)N(R 10 )2, -(haloC1-C6alkylene)-(CS)N(R 10 )2, -(haloC1-C6alkylene)-(SO)R 10 -(haloC1-C6alkylene)-(SO2)R 10 -(haloC1-C6alkylene)-N(R 10 )2or -O-(haloC1-C6alkylene)-(CO)OR 10 ; or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2-, -CH2CH2CH2- or -OCH2O- which is unsubstituted or substituted with at least one group selected from halo or -(CO)OR 10 ; or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2-, -CH2CH2CH2- or -OCH2O- which is unsubstituted or substituted with at least one group selected from halo or -(CO)OR

[0045] m represents 0, 1 or 2;

[0046] R 10 are each independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, haloC3-C6cycloalkyl, C3-C6cycloalkyl substituted with C1-C6alkyl, C3-C6cycloalkylC1-C6alkyl, aryl, heterocyclyl, or aryl or heterocyclyl substituted with at least one group selected from halo, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or haloC1-C6alkoxy.

[0047] In the definitions of the compounds of the above formula and in all the formulae below, the terms used, whether used alone or in a composite term, represent the following substituents: alkyl groups having more than two carbon atoms can be straight or branched. As in the composite term "-alkylene-OR 10"middle alkylene" can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, and the like. Alkyl groups are, for example, C1alkyl-methyl; C2alkyl-ethyl; C3alkyl-propyl such as n-propyl or isopropyl; C4alkyl-butyl such as n-butyl, isobutyl, t-butyl, or 2-butyl; C5alkyl-pentyl such as n-pentyl; C6alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl 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 in any position on each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where the double bond(s) can be in any position. Halogen is fluorine, chlorine, bromine, or iodine.

[0048] Unless otherwise specifically noted, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0049] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and that the description includes instances where the event or circumstance occurs and instances where it does not. For example, the term "optionally substituted" means that the specified atom or group is unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is to be understood as meaning that the group is substituted with one or more, identical or different, groups selected from those mentioned. In addition, the same or different substituents contained in identical or different groups are each independently selected, which can be the same or different. This applies equally to ring systems formed by different atoms and units. At the same time, the scope of the claims is to exclude those compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0050] In addition, unless specifically limited, the term "substituted" as used herein means substituted with 1, 2, 3, 4, or 5 groups; groups not marked with a specific position of attachment (including heterocyclyl, aryl, etc.) can be attached at any position, including to a C or N; if substituted, the substituents can likewise be substituted at any position, as long as the bonding rules are followed. For example, a heteroaryl group substituted with 1 methyl group may represent etc.

[0051] If various functional groups are present, the present application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0052] The method for preparing the substituted aryl amide compound or salt thereof, comprises the following steps:

[0053] (1) reacting a compound of general formula II or its salt (such as hydrochloride) with a compound of general formula III to obtain a compound of general formula I, and the reaction equation is as follows:

[0054] Alternatively, (2) preparing compound I through substitution or coupling reaction with compound IV as an intermediate,

[0055] wherein, P is OH or halogen, Q1 is halogen, and the definitions of other substituents W, M, R1, R2, R3, R4, R5, R6, R7, R8, R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are as described above.

[0056] Preferably, the reaction (1) is carried out in the presence of a solvent, a condensing agent and a base; more preferably, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU; the base is selected from at least one of an inorganic base (such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, Cs2CO3, KF, CsF, etc.) or an organic base (such as pyrazole, triethylamine, N,N diisopropyl ethylamine, pyridine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, t-BuOK, etc.); and the solvent is selected from at least one of an aromatic hydrocarbon (such as benzene, chlorobenzene or toluene), DMF, DMA, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane or ethyl acetate.

[0057] In addition, the compound represented by the general formula I can be produced according to the method described in PCT / JP2017 / 017241, PCT / JP2021 / 015856, etc.

[0058] The present application also discloses a miticidal composition comprising a biologically effective amount of at least one of the aforementioned substituted arylamide compounds or salts thereof; preferably, further comprising a formulation aid; more preferably, further comprising other effective ingredients.

[0059] The present application also discloses a method for controlling mites, comprising contacting the mites or the environment thereof with a biologically effective amount of the aforementioned substituted arylamide compound or salt thereof or the aforementioned composition.

[0060] The present application also discloses the use of the aforementioned arylamide compound or salt thereof or composition in the control of mites.

[0061] The present application also discloses an intermediate represented by the aforementioned formula II, III or IV.

[0062] According to the present application, salts of the compounds of the present application, such as salts with bases or acid addition salts, are all customary non-toxic salts, preferably agriculturally and / or physiologically acceptable salts. Preference is given to salts with inorganic bases, such as alkali metal salts (for example sodium, potassium or cesium salts), alkaline earth metal salts (for example calcium or magnesium salts), ammonium salts; or salts with organic bases, in particular with organic amines, such as triethylammonium, dicyclohexylammonium, N,N'-dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts; salts with inorganic acids (for example hydrochlorides, hydrobromides, dihydrogen sulfates, trihydrogen sulfates or phosphates); salts with organic carboxylic or sulfonic acids (for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates or 4-toluenesulfonates). It is known that tertiary amines such as some of the compounds of the present application are capable of forming N-oxides, which are likewise salts of the present application.

[0063] Depending on the nature of the substituents, the compounds of the formula I can exist in the form of geometric and / or optically active isomers or in the form of corresponding isomer mixtures of different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present application therefore includes pure stereoisomers as well as any mixtures of these isomers.

[0064] The active compounds according to the application are suitable for protecting plants and plant organs, for enhancing growth, for improving the quality of harvested material and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, that occur in agricultural, horticultural, animal-husbandry, forestry, park and leisure facilities, in the protection of stored products and materials and in the hygiene sector. They are preferably used as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The pests mentioned include:

[0065] Anoplura (Phthiraptera), for example Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.

[0066] Arachnida, for example, Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitertranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

[0067] Bivalva, for example, Dreissena spp.

[0068] Chilopoda, for example, Geophilus spp., Scutigera spp.

[0069] Coleoptera, for example, Acalymma vittatum, bean weevil (Acanthoscelides obtectus), Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderus spp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata, Limo- nia spp., Lyctus spp., Melanotus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monomerus spp., Naupactus xanthus, Oedema spp., Oto- melonus sibiricus, Ortygia postvittata, Otiorrhynchus sulcatus, Phaedon cochleariae, Ph- ylophaga spp., Phlyctinus spp., Phyllophaga spp., Phyllophaga cam Thomasa, Phyllo- phaga cuyabana, Phyllophaga helleri, Phyllophaga sp., Phyllopertha horticola, Phyl- lopertha spp., Popillia japonica, Ptinus spp., Rhigittus quadendus, Rhynchophorus fer- ruginosus, Rhynchophorus phoenicis, Sciaphila spp., Sitophilus spp., Sphenophorus spp., Stegobium paniceum, Sternechus spp., Synaptonoma spp., Tribolium spp., Trogoderma spp., Ypsolopha sylvella, and Zophobius spp.Leptinotarsa decemlineata, Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus, Melolontha spp., Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.

[0070] Collembola, for example, Onychiurus armatus.

[0071] Diplopoda, for example, Blaniulus guttulatus.

[0072] Diptera, for example, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp., Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia, Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.

[0073] Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.

[0074] Helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.), Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[0075] In addition, protozoa, such as Eimeria, can also be controlled.

[0076] Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Carvalhoia spp., Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

[0077] Homoptera, for example, Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphid spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilu shalli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp., Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp.The genera *Quadraspidiotus* spp., *Quesada gigas*, *Rastrococcus* spp., *Rhopalosiphum* spp., *Saissetia* spp., *Scaphoides titanus*, *Schizaphis graminum*, *Selenaspidus articulatus*, *Sogata* spp., *Sogatella furcifera*, *Sogatodes* spp., *Stictocephala festina*, *Tenalaphara malayensis*, *Tinocallis caryaefoliae*, *Tomaspis* spp., *Toxoptera* spp., *Trialeurodes* spp., and *Trioza* *Typhlocyba* spp., *Unaspis* spp., *Viteus vitifolii*, and *Zygina* spp.

[0078] Hymenoptera, for example, Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, and Vespa spp.

[0079] Isopoda, for example, woodlice (Armadillidium vulgare), comb beetles (Oniscus asellus), and ball beetles (Porcellio scaber).

[0080] Isoptera, for example, Acromyrmex spp., Atta spp., Cornitermes cumulans, Microtermes obesi, Odontotermes spp., and Reticulitermes spp.

[0081] Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora., Capua reticulana, Carpocapsa pomonella, Carposina niponensis., Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias insulana, Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholita molesta, Hedylepta indicata, Helicoverpa armigera, Heliothis spp., Hibernia defoliaria, Hyphantria cunea, Keiferia lycimora, Leucoptera spp., Lithocolletis spp., Lobesia botrana, Loxagrotis spp., Lymantria spp., Lyonetia spp., Malacosoma neustria, Maruca testulalis, Melanchra persicaria, Meliaethia spp., Momphidae, Operophtera spp., Orgyia spp., Ornea spp., Ostrinia nubilalis, Panolis flammea, Pammene spp., Pandemis spp., Paracolax spp., Parapedesa spp., Parasemia spp., Pectophora spp., Perileucoptera spp., Phalonia spp., Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., Phyllonorycter blankensteini, Phyllonorycter mulleri, Phyllonorycter quercifoliella, Phyllonorycter rorella, Phyllonorycter salisiani, Phyllonorycter spadix, Phyllonorycter stachydri, Phyllonorycter trifasciella, Phyllocoptruta oleivora, Pieris rapae, Platyptilia spp., Plodia interpunctella, Plutella xylostella, Pseudautomeris spp., Pseudoplusia includens, Rhyacionia spp., Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis spp., Spodoptera spp., Stathmopoda spp., Stomopteryx subseciva, Synanthedon spp., Thaumetopoea pityocampa, Tortrix spp., Trichophaga tapetzella, Tuta absoluta, Zeiraphera canadensis, Zeiraphera diniana, Zeiraphera furdara, Zeiraphera japonicana, Zeiraphera canadensis, Zeiraphera diniana, Zeiraphera furdara, Zeiraphera japonicana.), Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata, Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp., Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp., Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plusia spp., Plutella xylostella, Prays spp., Prodenia spp.*Protoparce* spp., *Pseudaletia* spp., *Pseudoplusia includens*, *Pyrausta nubilalis*, *Rachiplusia nu*, *Schoenobius* spp., *Scirpophaga* spp., *Scotia segetum*, *Sesamia* spp., *Sparganothis* spp., *Spodoptera* spp., *Stathmopoda* spp., *Stomopteryx subsecivella*, *Synanthedon* spp., *Tecia solanivora*, *Thermesia gemmatalis*, *Tinea pellionella*, *Tineola bisselliella*, *Tortrix* spp., *Trichoplusia* *Tuta absoluta*, and *Virachola* spp.

[0082] Orthoptera, for example, domestic cricket (Acheta domesticus), oriental cockroach (Blatta orientalis), German cockroach (Blattella germanica), Dichroplus spp., mole cricket (Gryllotalpa spp.), Madeira cockroach (Leucophaea maderae), locust (Locusta spp.), black locust (Melanoplus spp.), American cockroach (Periplaneta americana), and desert locust (Schistocerca gregaria).

[0083] Siphonaptera, for example, the genera *Ceratophyllus* spp. and *Xenopsylla cheopis*.

[0084] Synphyla, for example, Scutigerella spp.

[0085] Thysanoptera, for example Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.

[0086] Thysanura, for example Lepisma saccharina.

[0087] Plant parasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

[0088] If appropriate, the active compound combinations according to the application can also be used as herbicides, safeners, growth regulators, or as agents for improving plant properties, or as microbicides, for example fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsiaceae-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.

[0089] The present application also relates to formulations comprising at least one active compound according to the application and to the use of these formulations to prepare application forms as crop protection compositions and / or insecticides, for example drenches, drips and spray liquors. The application forms optionally comprise further crop protection agents and / or insecticides and / or activity-enhancing adjuvants such as, for example, penetration agents, for example plant oils (such as, for example, rapeseed oil, sunflower oil), mineral oils (such as, for example, paraffin oil), alkyl esters of vegetable fatty acids (such as, for example, rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates, and / or spreaders such as, for example, alkylsilicones and / or salts, for example organic or inorganic ammonium or phosphonium salts (such as, for example, ammonium sulfate or dihydrogen ammonium phosphate), and / or retention promoters such as, for example, dioctyl sulfosuccinate or hydroxypropyl guar polymers, and / or wetters such as, for example, glycerol and / or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0090] Conventional formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), oil-in-water emulsions (EW), suspensions (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); the above and other possible formulation types are described, for example, by Crop Life International in the Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specification, 2004, ISBN: 9251048576. In addition to one or more active compounds according to the application, the formulations optionally comprise further agrochemically active compounds.

[0091] Formulations or application forms which comprise adjuvants (for example extenders, solvents, spreaders, carriers, emulsifiers, dispersants, frost protection agents, biocides, thickeners and / or further adjuvants, for example adjuvants) are preferred. Adjuvants in the present application are components which enhance the biological effect of the formulation, while the component itself does not have a biological effect. Examples of adjuvants are agents which promote retention, throw, adhesion to the leaf surface or penetration.

[0092] The formulations are produced in known manner, for example by mixing the active compounds with adjuvants, such as extenders, solvents and / or solid carriers and / or further adjuvants, such as surface-active agents. The formulations are prepared before use or during use in suitable devices.

[0093] The substances used as adjuvants are suitable for imparting specific properties, such as certain physical, technical and / or biological properties, to the active compound preparations and / or to the application forms prepared therefrom, such as ready-to-use crop protection compositions, for example spray liquors or seed dressings.

[0094] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, such as aromatic and aliphatic hydrocarbons, such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes, alcohols and polyols if appropriate also substituted, etherified and / or esterified, ketones, such as acetone, cyclohexanone, esters including fatty and oil esters and (poly)ethers, unsubstituted and substituted amines, amides, lactams, such as N-alkylpyrrolidones, and lactones, sulfones and sulfoxides, such as dimethyl sulfoxide.

[0095] If the extender used is water, it is also possible to use, for example, organic solvents as cosolvents. Suitable liquid solvents are, inter alia, aromatic compounds, such as xylene, toluene or alkyl-naphthalenes, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or dichloromethane, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and also water.

[0096] In principle, all suitable solvents can be used, examples of suitable solvents being aromatic hydrocarbons, such as xylene, toluene or alkyl-naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or dichloromethane, aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulfoxide, and also water.

[0097] In principle, all suitable carriers can be used. Useful carriers include, inter alia, ammonium salts and pulverized natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomite, and pulverized synthetic minerals, such as highly dispersed silicic acid, alumina and natural and synthetic silicates, resins, waxes and / or solid fertilizers. It is also possible to use mixtures of the said carriers. Suitable solid carriers for granules are, for example, pulverized and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic powders and granules of organic materials, such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.

[0098] It is also possible to use liquefied gaseous fillers or solvents. Fillers or carriers which are particularly suitable are those which are gaseous at room temperature and at atmospheric pressure, for example propellants for aerosol sprays, such as halogenated hydrocarbons and also butane, propane, nitrogen and carbon dioxide.

[0099] Examples of emulsifiers and / or foaming agents, dispersants or wetting agents, of ionic or nonionic character, or a mixture of these surfactants, include polyacrylic acid salts, lignosulphonic acid salts, salts of phenol- or naphthalenesulphonic acid, condensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines or with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (for example alkyl taurine salts), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyvalent alcohols, and derivatives of compounds containing sulphate, sulphonate and phosphate groups, for example alkyl aryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or protein hydrolysates, lignosulphite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the active compounds and / or one of the inert carriers is not soluble in water and the application takes place in water.

[0100] Further adjuvants which can be present in the formulations and in the use forms derived from them include dyes, such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0101] Further constituents can be stabilisers, for example, for protection against oxidation, against light, against the action of water or of other reagents, or else other agents for increasing chemical and / or physical stability. Foaming or antifoaming agents can also be present.

[0102] It is also possible to add tackifiers such as carboxymethylcellulose, and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyacrylic acid, or other natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, as further adjuvants, which are preferably present in the formulations and in the use forms derived from them. Mineral and vegetable oils can also be present as further adjuvants.

[0103] Optionally, further adjuvants can also be present in the formulations and in the use forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetration agents, retention promoters, stabilizers, sequestering and chelating agents, complexing agents, wetting agents, spreading agents. In general, the active compounds can be combined with any solid or liquid additive commonly used in the art of formulating.

[0104] Useful retention-promoting agents include all those substances which lower the dynamic surface tension, such as, for example, dioctyl sulfosuccinate; or substances which increase the viscoelasticity, such as, for example, hydroxypropyl guar polymers.

[0105] In the context of the present application, useful penetrants are all those substances which are generally used to improve the penetration of agrochemical active compounds into plants. In the context of the present application, penetrants are defined by their ability to penetrate from the (usually aqueous) application liquor and / or spray coating into the plant cuticle and thus to improve the mobility of the active compounds in the cuticle. Examples include alkanol alkoxylates, such as, for example, coconut oil fatty acid ethoxylate (10) or isotridecyl ethoxylate (12); fatty acid esters such as, for example, rapeseed oil methyl ester or soybean oil methyl ester; fatty amine alkoxylates such as, for example, tallow amine ethoxylate (15); or ammonium and / or phosphonium salts such as, for example, ammonium sulfate or dihydrogen ammonium phosphate.

[0106] The formulations comprise preferably from 0.00000001 to 98% by weight of active ingredient or more preferably from 0.01 to 95% by weight of active ingredient, more preferably from 0.5 to 90% by weight of active ingredient, based on the weight of the formulation.

[0107] The active ingredient content of the use forms (crop protection compositions) produced from the formulations can vary within a wide range. The active ingredient concentration of the use forms can generally be from 0.00000001 to 95% by weight of active ingredient, preferably from 0.00001 to 1% by weight of active ingredient, based on the weight of the use form. Application is effected in the customary manner appropriate for the use form.

[0108] The active compounds according to the application can be used as such or in the form of their formulations, which include mixtures with one or more suitable fungicides, bactericides, acaricides, nematicides, insecticides, microbicides, fertilizers, attractants, sterilants, synergists, safeners, semiochemicals and / or plant growth regulators, which aim, for example, at broadening the activity spectrum, at prolonging the duration of action, at increasing the rate of action, at preventing repellence or at preventing the development of resistance. Furthermore, the plant growth can be improved by those combinations which improve the abiotic stress factor tolerance, for example the tolerance to high or low temperatures, to drought or to salt content in water and / or in the soil. Also the quality of the flowering and fruiting, the germination performance and root development can be optimized, the harvesting made easier and the yield increased, ripening accelerated, the quality and / or the nutritional value of the harvested products improved, the storage life of the harvested products prolonged and / or their processability improved. In general, the combination of the active compounds according to the application and the co-ingredients leads to a synergistic effect, i.e. the efficacy of the mixture is greater than the sum of the efficacy of the individual components. The combinations can generally be used in the form of premixes, tank mixes or freshly prepared mixtures and can also be used in seed applications.

[0109] Particularly advantageous co-ingredients are, for example, those listed below.

[0110] Insecticides / acaricides / nematicides:

[0111] The active compounds indicated here by their common names are known and described, for example, in The Pesticide Manual (14th Edition, British Crop Protection Council 2006), or are accessible on the internet (for example http: / / www.alanwood.net / pesticide).

[0112] (1 ) Acetylcholinesterase (AChE) inhibitors, for example carbamates, such as alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb;

[0113] or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, O-(methoxyamidothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulphotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon;Temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion.

[0114] (2) GABA-gated chloride ion channel antagonists, such as the cyclo- diene organochlorines, for example, chlordane and endosulfan;

[0115] or the phenylpyrazoles (fiprols), for example, ethiprole, fipronil.

[0116] (3) sodium channel modulators / potassium-dependent sodium channel blockers, e.g., pyrethroids, e.g.,acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopropyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrine (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin, transfluthrin,

[0117] or DDT; or methoxychlor.

[0118] (4) agonists of nicotinic acetylcholine receptors (nAChRs), such as neonicotinoids, e.g., acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.

[0119] (5) allosteric activators of nicotinic acetylcholine receptors (nAChRs), such as spinosyns, e.g., spinetoram and spinosad.

[0120] (6) chloride channel activators, e.g., avermectins / milbemycins, e.g., abamectin, emamectin-benzoate, lepimectin, milbemycin.

[0121] (7) juvenile hormone mimics, e.g., juvenile hormone analogs, e.g., hydroprene, kinoprene, methoprene; or fenoxycarb; or pyriproxifen.

[0122] (8) active substances of unknown or non-specific mode of action, e.g., halogenated hydrocarbons, e.g., bromomethane, other halogenated hydrocarbons; or chloropicrin; or sulfuryl chloride; or borax; or tartar emetic.

[0123] (9) selective antifeedants, e.g., pymetrozine; or flonicamid.

[0124] (10) mite growth inhibitors, e.g., clofentezine, hexythiazox, diflovidazin; or etoxazole.

[0125] (11) Insect intestinal membrane microbial interference agents, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, BT crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0126] (12) Oxidative phosphorylation inhibitors, ATP interfering agents, such as diafenthiuron; or organotin acaricides, such as azocyclotin, cyhexatin, fenbutatin-oxide; or propargite; or tetradifon.

[0127] (13) Oxidative phosphorylation uncoupling agents that function through a discontinuous H proton gradient, such as chlorfenapyr, dinitrocresol (DNOC), and sulfluramid.

[0128] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

[0129] (15) Chitin biosynthesis inhibitors, type 0, for example, bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.

[0130] (16) Chitin biosynthesis inhibitors, type 1, for example, buprofezin.

[0131] (17) Molting disruptors, for winged insects, such as cyromazine.

[0132] (18) ecdysone receptor agonists, for example, chromafenozide, halofenozide, methoxyfenozide, tebufenozide.

[0133] (19) octopaminergic agonists, for example, amitraz.

[0134] (20) complex III electron transport inhibitors, for example, hydramethylnon, or acequinocyl, or fluacrypyrim.

[0135] (21) complex I electron transport inhibitors, for example, MET I acaricides, for example, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone (Derris).

[0136] (22) voltage-dependent sodium channel blockers, for example, indoxacarb; or metaflumizone.

[0137] (23) acetyl CoA carboxylase inhibitors, for example, tetramic acids and derivatives thereof, for example, spirodiclofen, spiromesifen, spirotetramat.

[0138] (24) complex IV electron transport inhibitors, for example, phosphines, such as aluminium phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanides.

[0139] (25) complex II electron transport inhibitors, for example, cyenopyrafen.

[0140] (28) ryanodine receptor modulators, for example, diamides, for example, chlorantraniliprole and flubendiamide.

[0141] Other active ingredients with unknown or undetermined mechanism of action, such as, for example, amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, cyantraniliprole (cyazypyr), cyflumetofen, dicofol, diflovidazin, fluensulfone, flufenerim, flufiprole, fluopyram, fufenozide, imidaclothiz, iprodione, meperfluthrin, pyridalyl, Pyrifluquinazon, tetramethylfluthrin, iodomethane; and formulations based on Bacillus firmus (in particular the CNCM 1-1582 strain, such as, for example, VOTiVO TM ,BioNem) or the following known active compounds:

[0142] 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3- chloropyridin-2-yl)-1 H-pyrazole-5-carboxamide (known from WO 2005 / 077934), 4-{[(6- bromopyridin-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO 2007 / 115644), 4-{[(6-fluoropyridin-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one (known from WO 2007 / 115644), 4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2- fluoroethyl)amino}furan-2(5H)-one (known from WO 2007 / 115644), 4-{[(6-chloropyridin- 3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO 2007 / 115644), Flupyradifurone, 4-{[(6-chloro-5-fluoropyridin-3-yl)methyl](methyl)amino}furan-2(5H)-one (known from WO 2007 / 115643), 4-{[(5,6-dichloropyridin-3-yl)methyl](2- fluoroethyl)amino}furan-2(5H)-one (known from WO 2007 / 115646), 4-{[(6-chloro-5- fluoropyridin-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from WO 2007 / 115643), 4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from EP-A-0 539 588), 4-{[(6-chloropyridin-3-yl)methyl](methyl)amino}furan-2(5H)-one (known from EP-A-0 539 588), {[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ 4 -sulfanylidene}carbamidine (known from WO 2007 / 149134) and its diastereomers {[1 R)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ 4 -sulfanylidene}carbamidine (A) and {[1 S)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ 4 -sulfanylidene}carbamidine (B) (known from WO 2007 / 149134) and sulfoxaflor and its diastereomers [(R)-methyl(oxido){(1 R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4 -sulfanylidene}carbamidine (A1) and [(S)-methyl(oxido){(1 S)-1-[6- (trifluoromethyl)pyridin-3-yl]ethyl}-λ 4- a sulfϊnyl]cyanamide (A2), known as diastereomeric set A (from WO 2010 / 074747, WO 2010 / 074751), [(R)-methyl(oxido){(1 S)-1 -[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4 - a sulfϊnyl]cyanamide (A2), known as diastereomeric set A (from WO 2010 / 074747, WO 2010 / 074751), [(R)-methyl(oxido){(1 S)-1 -[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4- sulfanyl]cyanamides (B2), known as diastereomeric group B (from WO 2010 / 074747, WO 2010 / 074751), and 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9- azadi spiro[4.2.4.2]tetradeca-11 -ene-10-one (known from WO 2006 / 089633), 3-(4'-fluoro- 2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3-en-2-one (known from WO 2008 / 067911), 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3- (trifluoromethyl)-1 H-1,2,4-triazol-5-amine (known from WO 2006 / 043635), [(3S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylate (known from WO 2008 / 066153), 2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulfonamide (known from WO 2006 / 056433), 2-cyano-3-(difluoromethoxy)-N-methylbenzenesulfonamide (known from WO 2006 / 100288), 2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulfonamide (known from WO 2005 / 035486), 4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazol-3-amine 1,1-dioxide (known from WO 2007 / 057407), N-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazol-2- amine (known from WO 2008 / 104503), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5- fluorospiro[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3- en-2-one (known from WO 2009 / 049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8- diazaspiro[4.5]dec-3-en-4-yl ethylcarboxylate (known from WO 2009 / 049851), 4-(but-2- ynyl-1 -yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160), (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,3-trifluoropropyl)propanedinitrile (known from WO 2005 / 063094), (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,4,4,4-pentafluorobutyl)propanedinitrile (known from WO 2005 / 063094), 8-[2-(cyclopropylmethoxy)-4-(trifluoromethyl)phenoxy]-3-[6- (trifluoromethyl)pyridazin-3-yl]-3-azabicyclo[3.2.1]octane (known from WO 2007 / 040280), Flometoquin, PF1364 (CAS-Registry-Number 1204776-60-2) (known from JP 2010 / 018586), 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1 H- 1,2,4-triazol-1 -yl)benzonitrile (known from WO 2007 / 075459), 5-[5-(2-chloropyridin-4-yl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1 H-1,2,4-triazol-1 - yl)benzonitrile (known from WO 2007 / 075459), 4-[5-(3,5-dichlorophenyl)-5- (trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2- trifluoroethyl)amino]ethyl}benzamide (known from WO 2005 / 085216), 4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](methyl)amino}-1,3-oxazol-2(5H)-one (all known from WO 2010 / 005692), NNI-0711 (known from WO 2002 / 096882), 1 -acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)-3- isobutylphenyl]-N-isobutyryl-3,5-dimethyl-1 H-pyrazole-4-carboxamide (known from WO 2002 / 096882), 2-[2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3- methylbenzoyl]-2-methylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3- methylbenzoyl]-2-ethylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3- methylbenzoyl]-2-methylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]- 1,2-diethylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]- 2-ethylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), (5RS,7RS; 5RS,7SR)-1 -(6-chloro-3-pyridinylmethyl)-1,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5- propoxyimidazo[1,2-a]pyridine (known from WO 2007 / 101369), 2-{6-[2-(5-fluoropyridin-3-yl)- 1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine (known from WO 2010 / 006713), 2-{6-[2-(pyridin-3-yl)- 1,3-[3-(3-thiazol-5-yl]pyridin-2-yl}pyrimidine (known from WO 2010 / 006713), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-1 H-tetrazol-1 -yl]methyl}-1 H-pyrazole-5-carboxamide (known from WO 2010 / 069502), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1 H-pyrazole-5-carboxamide (known from WO 2010 / 069502), N-[2-(tert-Butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-1 H-tetrazol-1-yl]methyl}-1 H-pyrazole-5-carboxamide (known from WO 2010 / 069502), N-[2-(tert-Butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1 H-pyrazole-5-carboxamide (known from WO 2010 / 069502), (1 E)-N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-(2,2-difluoroethyl)formimidamide (known from WO 2008 / 009360), N-[2-(5-amino-1,3,4-thiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1 H-pyrazole-5-carboxamide (known from CN 102057925), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethyl-1-methylhydrazinecarboxylic acid methyl ester (known from WO 2011 / 049233).

[0143] It is also possible to mix the active compounds according to the application with other known active compounds, for example herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving plant properties.

[0144] When used as pesticides, the active compounds according to the application can also be present in their commercially customary formulations and in the use forms prepared from these formulations with surfactants or extenders, which are not active themselves, such as mineral salts, natural- or synthetic- polymers, or with solid or liquid carriers, such as finely divided carbon black, carbonates, natural or synthetic silicates, silica gels, silicic acid derivatives, or water.

[0145] When used as pesticides, the active compounds according to the application can also be present in their commercially customary formulations and in the use forms prepared from these formulations with inhibitors, which reduce the degradation of the active compounds after their application to the surface of the habitat of the plants, to the plant parts or in the plant tissues.

[0146] All plants and their parts can be treated in accordance with the application. Plants are understood as meaning all plants and their parts, e.g. wild-type plants and plants that have been modified by conventional methods of breeding and selection, or by mutagenesis and / or by genetic engineering. The plants comprise the crop plants which can be obtained by conventional methods of breeding or by mutagenesis and / or by genetic engineering, including the plants which are protected by plant breeders' rights or which are not protected by plant breeders' rights. The parts of plants are understood as meaning all above-ground and below-ground parts and plant organs, e.g. shoot, leaf, flower and root, examples which include are leaf, needle, stem, trunk, flower, fruit, seed, root, tuber and rhizome. The parts also include harvestable parts, and vegetative and generative propagation material, e.g. cuttings, tubers, rhizomes, offshoots and seeds.

[0147] The treatment of plants and plant parts according to the application with the active compounds is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space, by the customary treatment methods, for example by immersion, spraying, vaporizing, fogging, spreading, brushing on, injecting, and, in the case of propagation material, in particular seeds, also by coating one or more layers.

[0148] As mentioned above, all plants and their parts can be treated in accordance with the application. In a preferred embodiment, wild-type plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods of breeding, are treated and their parts are treated. The terms "parts" or "parts of plants" or "plant parts" are to be understood in accordance with the plant parts mentioned above.

[0149] More preferably, the plants treated in accordance with the application are plant cultivars or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion and their parts. The plant cultivars include the plants which have been modified by genetic engineering methods, if appropriate in combination with conventional methods of breeding, and their parts.

[0150] Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the application can also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and / or a widening of the activity spectrum and / or an increase in the activity of the compounds and compositions used according to the application, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality of the harvest, or better storage characteristics of the harvested material, or other advantages can be achieved.

[0151] Preferred transgenic plants or plant cultivars (i. e. those that have been modified by genetic engineering) which are to be treated in accordance with the application include all plants, whether or not they have been modified by genetic engineering, to which traits have been transferred by genetic engineering, including the transfer of traits conferring resistance of the plants to harmful insects, fungi, bacteria, viruses and / or worms, the transfer of traits conferring increased productivity under stress conditions, e. g. drought, heat, cold, salinity, etc., the transfer of traits (e. g. corn, cotton, soya beans), (e. g. corn), (e. g. corn), (cotton), (cotton), and (potato). Examples of plants which can be mentioned are corn plants, cotton plants, soya bean plants and potato plants which are marketed under the brand names Herculex® corn, cotton, soybean), Liberty Link® (with phosphinothricin tolerance, e.g. canola), Roundup Ready® (with glyphosate tolerance, e.g. corn, cotton, soybean), Liberty Link® (with phosphinothricin tolerance, e.g. canola), Roundup Ready® (with glyphosate tolerance, e.g. corn, cotton, soybean), Roundup Ready® (with glyphosate tolerance, e.g. corn, cotton, soybean). Plants that can be mentioned with herbicide resistance (plants bred in the conventional manner for herbicide tolerance) include the commercial varieties under the designations

[0152] The plants mentioned above can be treated in a particularly advantageous manner with the compounds of the formula I according to the application or the active compound mixtures according to the application. The preferred ranges of active compounds or mixtures mentioned above also apply to the treatment of the plants. Particular emphasis is placed on the treatment of plants with the compounds or mixtures specifically mentioned according to the application.

[0153] The active compounds according to the application are not only active against pests, hygiene pests and stored-product pests in the plant, but also against animal parasites (ectoparasites and endoparasites) in the veterinary sector, such as hard ticks, soft ticks, mites, spider mites, flies (biting and sucking), parasitic fly larvae, lice, biting lice, feather lice and fleas.

[0154] The active compounds of the formula I according to the application are also suitable for controlling arthropods that attack agricultural productive livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, water buffalo, rabbits, domestic chicken, turkeys, ducks, geese and bees, other pet animals, such as dogs, cats, cage birds and ornamental fish, and test animals, such as hamsters, guinea pigs, rats and mice. The control of the arthropods is aimed at reducing mortality and yield (meat, milk, wool, skin, eggs, honey etc.) losses, thus making animal husbandry more economical and more convenient by using the active compounds according to the application.

[0155] The active compounds according to the application are used in the veterinary sector and in animal husbandry in a known manner, in the form of enteral administration, for example by means of tablets, capsules, drinks, drenches, granules, pastes, pellets, feed-through and suppositories; parenteral administration, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal etc.), implants; nasal administration; dermal administration, for example in the form of dips or baths, sprays, pour- ons and spot- ons, rinses and dusts, and by means of models, for example collars, ear tags, tail tags, limb bands, halters, markers etc., comprising the active compounds.

[0156] For use on livestock, poultry, domestic animals, etc., the active compounds of the formula I can be used as formulations, e.g. dusts, emulsions, flowables, including amounts of from 1 to 80% by weight of active compound, directly or after dilution of 100 to 10 000 times, or in the form of a chemical bath.

[0157] The term technical material in the present application is to be understood as meaning non-living materials, such as, for example, preferably plastics, adhesives, mastics, paper and board, leather, wood and wood-based materials and coating compositions.

[0158] The ready-to-use compositions can optionally also comprise further insecticides and, optionally, also one or more fungicides.

[0159] Furthermore, the compounds according to the application can be used for protecting objects which come into contact with salt or brackish water, in particular ship hulls, screens, nets, buildings, mooring equipment and signalling systems, from fouling.

[0160] Furthermore, the compounds according to the application can be used as antifouling compositions, either alone or in combination with other active compounds.

[0161] The active compounds according to the application are also suitable for controlling animal pests in the domestic field, hygiene and the protection of stored products, in particular insects, arachnids and mites which occur in enclosed spaces such as dwellings, factory premises, offices, vehicle cabins and the like. They can be used, alone or in combination with other active compounds and with auxiliaries, in domestic insecticidal products for controlling the pests mentioned. They are effective against sensitive and resistant species and against all stages of development.

[0162] In the field of domestic insecticides, they can be used alone or in combination with other suitable active compounds, such as phosphonates, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.

[0163] They are used in the form of aerosols, pressure-free spray products such as pump and atomizer sprays, automatic misting systems, fumigants, foams, gels, evaporative products with evaporator tablets made of cellulose or plastic, liquid, gel and film evaporators, propellant-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags or moth gels, as granules or powders in bait for scattering or in bait stations. DETAILED DESCRIPTION

[0164] The following examples are intended to illustrate the application and should not be construed as limiting the application in any way. The scope of the application sought to be protected is defined by the claims.

[0165] In view of the economy and diversity of the compounds, we have synthesized a number of compounds, among which some are selected and listed in Table 1 below. The structures of the specific compounds and the corresponding compound information are shown in Table 1-2. The compounds in Table 1 are only for better illustrating the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present application is limited to the following compounds.

[0166] Table 1 Compound structure

[0167] Table 2 Compound 1 H NMR

[0168] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. The starting materials can be purchased from commercial suppliers or prepared by known literature methods or as illustrated. Those skilled in the art will appreciate that other synthetic routes can be used to synthesize the compounds of the present application. Although specific starting materials and conditions are depicted below, other similar starting materials and conditions can readily be found by those skilled in the art and are included in the present application. In addition, the synthetic methods described below can be further modified using conventional chemistry methods known to those skilled in the art in light of the disclosure herein. For example, protecting groups for appropriate groups during the reaction process and the like.

[0169] The following method examples are provided to facilitate a further understanding of the preparation methods of the present application, the specific materials, quantities, and conditions used are determined to be the best modes for carrying out the application and are not intended to limit the reasonable scope thereof. The reagents used in the synthesis of the compounds described hereinafter are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0170] The following examples illustrate the preparation of representative compounds. The synthesis of other compounds is analogous and is not described in detail.

[0171] 1. Synthesis of compound 3

[0172] (1) Under ice-bath condition, 20% sodium ethoxide solution (2.19 g, 32.2 mmol) was added dropwise to a solution of 3-2 (2.71 g, 32.2 mmol) in ethanol. The mixture was stirred for 15 min under ice-bath condition, and a solution of compound 3-1 (6 g, 32.2 mmol) in ethanol was added dropwise. After the addition was completed, the mixture was stirred overnight. The reaction solution was concentrated, diluted with dilute hydrochloric acid to precipitate a solid, and filtered. The solid was washed with water and dried to give compound 3-3 (4.4 g, yield 66%).

[0173] (2) Compound 3-3 (4.4 g, 21.4 mmol) was dissolved in 50 mL of dichloroethane, and a catalytic amount of DMF was added dropwise. POBr3 (18.35 g, 64.1 mmol) was added dropwise, and after the addition was completed, the mixture was warmed to 100°C and stirred for 4 h. The reaction was monitored by LCMS, and after cooling, the mixture was poured into ice water and extracted with dichloromethane three times. The organic phase was concentrated and purified by sample preparation (EA:PE = 1:3) to give compound 3-4 (5 g, yield 87%).

[0174] (3) A single-neck flask was charged with compound 3-4 (3.0 g, 11 mmol) dissolved in THF (30 mL), and sodium hydroxide solution (492 mg, 12.3 mmol dissolved in 30 mL of water) was added. The temperature was maintained below 25°C, and the mixture was stirred for 1 h. After the reaction was completed, the mixture was monitored by LCMS, and the pH of the reaction solution was adjusted to be acidic with dilute hydrochloric acid. The mixture was extracted with ethyl acetate. The organic phase was dried and concentrated to give crude compound 3-5 (2.5 g, yield 93%).

[0175] (4) At room temperature, 3-5 (2.5 g, 10.4 mmol) was dissolved in DCM, and a solution of 3-6 (2.1 g, 11.5 mmol) in DCM was added dropwise, followed by the addition of HATU (5.9 g, 15.5 mmol) and triethylamine (3.1 g, 31 mmol). After dropwise addition was completed, stirring was performed at room temperature for 30 min. LCMS monitoring was performed until the reaction was complete, and the reaction mixture was directly concentrated and stirred, followed by normal phase purification (EA:PE = 1:3) to obtain intermediate 3-7 (yellow oil, 3 g, yield 71%).

[0176] (5) Compound 3-7 (0.15 g, 0.37 mmol), 3-8 (0.11 g, 0.44 mmol), potassium carbonate (0.15 g, 1.1 mmol), and a catalytic amount of Pd(dppf)Cl2were dissolved in 1,4-dioxane (10 mL) and water (1 mL), and stirring was performed at 100°C under nitrogen for 4 h. Extraction was performed with ethyl acetate, and the organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA:PE = 1:5) to obtain compound 3 (pale yellow solid, 0.11 g, yield 67%).

[0177] 2. Synthesis of compound 8

[0178] Compound 3-6 (0.1 g, 0.55 mmol) was dissolved in a dichloromethane solution at room temperature, and compound 8-1 (0.18 g, 0.6 mmol), HATU (0.3 g, 0.82 mmol), and triethylamine (0.33 g, 3.3 mmol) were added while stirring. Stirring was continued for 3 h, and LCMS monitoring was performed until the reaction was complete. Water was added to the reaction mixture, which was diluted with dichloromethane, and the aqueous phase was extracted with dichloromethane three times. The combined organic phase was concentrated and stirred, and normal phase purification (EA:PE = 1:3) was performed to obtain compound 8 (white solid, 0.15 g, yield 58%).

[0179] 3. Synthesis of compound 37

[0180] (1) 37-1 (500 mg, 2.05 mmol) was dissolved in 15 ml of ACN, and 37-2 (219 mg, 2.25 mmol) and TEA (621 mg, 6.15 mmol) were added at 0°C, and the reaction was performed for 2 h. After the reaction was completed, water was added to quench the reaction, and EA was added to extract the organic phase. The organic phase was dried and subjected to normal phase purification to obtain 37-3 (260 mg, yield 38%).

[0181] (2) 37-3 (260 mg, 0.97 mmol), 37-4 (184 mg, 0.97 mmol), K2CO3 (402 mg, 2.91 mmol) and Pd(dppf)Cl2 (40 mg, 0.05 mmol) were dissolved in 15 ml 1,4-dioxane, N2 protection, 100 °C for 3 h. After the reaction was completed, direct sample was purified by normal phase to obtain 37-5 (370 mg, yield 73%).

[0182] (3) 37-5 (360 mg, 1.03 mmol) was dissolved in a mixed solvent of MeOH / THF / H2O (10 ml / 5 ml / 3 ml), NaOH (102 mg, 2.56 mmol) was added, and the reaction was carried out for 3 h. After the reaction was completed, the pH was adjusted to be acidic, extracted with EA, and the EA phase was dried and directly spin-dried to obtain 37-6 (300 mg, yield 87%).

[0183] (4) 37-6 (100 mg, 0.28 mmol), hydrochloride salt of 3-6 (51 mg, 0.28 mmol), HATU (160 mg, 0.42 mmol) and TEA (85 mg, 0.84 mmol) were dissolved in 15 ml DCM, and the reaction was carried out for 1 h. After the reaction was completed, direct sample was purified to obtain compound 37 (60 mg, yield 41%).

[0184] 4. Synthesis of compound 45

[0185] 3-7 (150 mg, 0.37 mmol) was dissolved in a mixed solvent (1,4-dioxane 20 ml, water 2 ml), 45-1 (109 mg, 0.45 mmol), potassium carbonate (153 mg, 3 eq) and Pd(dppf)Cl2 (9 mg, 0.01 mmol) were added respectively. Nitrogen protection, 100 °C for 4 h, LCMS monitoring until the reaction was completed. The reaction was quenched by pouring into water, extracted with ethyl acetate three times, the organic phase was combined, washed with saturated brine, dried with anhydrous sodium sulfate, concentrated and stirred, and purified by normal phase to obtain compound 45 (100 mg, yield 61%).

[0186] 5. Synthesis of compound 47

[0187] Compound 3-7 (0.15 g, 0.37 mmol), compound 47-1 (0.09 g, 0.45 mmol), potassium carbonate (0.15 g, 1.1 mmol) and catalytic amount of Pd(dppf)Cl2were dissolved in 1,4-dioxane (10 mL) and water (1 mL), stirred at 100 °C for 4 h under nitrogen. Extracted with ethyl acetate, washed with water and saturated brine, dried and concentrated, the residue was purified by column chromatography (EA:PE = 1:4) to give compound 47 (light yellow solid, 0.1 g, yield 57%).

[0188] 6. Synthesis of compound 67

[0189] Compound 67-1 (0.1 g, 0.55 mmol) was dissolved in dichloromethane at room temperature, compound 8-1 (0.16 g, 0.6 mmol), HATU (0.27 g, 0.82 mmol) and triethylamine (0.14 g, 1.65 mmol) were added under stirring. Stirring was continued for 3 h, the reaction was monitored by LCMS. Water was added to the reaction, diluted with dichloromethane, the aqueous phase was extracted with dichloromethane three times, the organic phases were combined, concentrated and purified by normal phase (EA:PE = 1:3) to give compound 67 (white solid, 0.075 g, yield 29%).

[0190] 7. Synthesis of compound 96

[0191] Compound 3-7 (200 mg) was dissolved in 10 mL dioxane and 1 mL water, 96-1 (1.2 equiv.), potassium carbonate (3.0 equiv.) and 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride (0.05 equiv.) were added sequentially at room temperature, after nitrogen replacement, the reaction was elevated to 80 °C overnight. Silica gel was added, and the product was purified by column chromatography to give compound 96 (white solid, 75 mg, yield 35%).

[0192] 8. Synthesis of compound 99

[0193] Compound 3-7 (200 mg) was dissolved in 15 mL EA, 99-1 (1.1 equiv.), CuI (1.2 equiv.) and bis(triphenylphosphine)palladium dichloride (0.05 equiv.) were added sequentially under stirring at room temperature, after nitrogen replacement, the reaction was elevated to 80 °C overnight. Silica gel was added, and the product was purified by column chromatography to give compound 99 (yellow solid, 175 mg, yield 83%).

[0194] 9. Synthesis of compound 100

[0195] Compound 3-7 (200.0 mg, 0.5 mmol) was dissolved in acetonitrile, compound 100-1 (126.2 mg, 0.74 mmol), cuprous iodide (19.1 mg, 0.01 mmol), triethylamine (101.0 mg, 1.0 mmol) and dichlorobis(triphenylphosphine)palladium (229.0 mg, 0.25 mmol) were added, the system was replaced with nitrogen three times, and the reaction was carried out at 80°C overnight. The reaction was monitored by LCMS. The positive phase was purified after concentration to obtain compound 100 (yellow solid, 85.0 mg, yield 34.8%).

[0196] 10. Synthesis of compound 104

[0197] (1) Compound 3-7 (1000 mg, 2.48 mmol) was dissolved in DMF, compound DIPEA (640 mg, 4.96 mmol) and compound 104-1 (407 mg, 2.97 mmol) were added, and the reaction was carried out at 100°C overnight. The reaction was monitored by LCMS. The system was poured into water, extracted with ethyl acetate, and the organic phase was washed with saturated brine 4-5 times. The organic phase was concentrated and purified by positive phase to obtain compound 104-2 (white oil, 890 mg, yield 78.0%).

[0198] (2) Compound 104-2 (640 mg, 1.39 mmol) was dissolved in trifluoroacetic acid and the reaction was carried out at 80°C for half an hour. The reaction was monitored by LCMS. Concentration and positive phase purification obtained compound 104 (white solid, 300 mg, yield 63.4%).

[0199] 11. Synthesis of compound 114

[0200] Compound 3-7 (0.20 g, 1.00 eq) was added to 5 mL of DMF, 114-1 (0.10 g, 1.5 eq), cuprous chloride (7.3 mg, 0.15 eq), K2CO3 (0.25 g, 3.00 eq) and N,N'-dimethylethylenediamine (6.5 mg, 0.15 eq) were added, the system was protected by nitrogen and the reaction was carried out at 120°C for 2 h. Extraction was carried out with EA and H2O, the organic phase was collected, dried over anhydrous sodium sulfate, and the sample was stirred and purified by positive phase to obtain compound 114 (70 mg, yield 35%) as a yellow solid.

[0201] 12. Synthesis of compound 115

[0202] (1) Compound 115-1 (2.58 g) was dissolved in 35 mL of acetonitrile, and PO(OEt3)2CN (1.5 equiv.), trimethylsilyl cyanide (1.5 equiv.), and TEA (3.0 equiv.) were sequentially added thereto with stirring at room temperature, and the mixture was heated to 82°C and reacted overnight. Silica gel was added to the reaction mixture, and column chromatography was performed to separate and purify the product, thereby obtaining compound 115-2 (2.1 g, yield 79%) as a yellow solid.

[0203] (2) Compound 115-2 (1.0 g) was dissolved in 20 mL of ethanol, and DIEA (3.0 equiv.) and hydroxylamine hydrochloride (2.0 equiv.) were sequentially added thereto with stirring at room temperature, and the mixture was heated to 80°C and reacted for 4 h. After the reaction was completed, ethanol was distilled off, and water was added to dilute the reaction mixture. The reaction mixture was extracted with EA three times, and the organic layers were combined and washed with saturated brine. The organic layer was concentrated to obtain compound 115-3 (0.855 g, yield 76%) as a white solid.

[0204] (3) Compound 115-3 (0.855 g) was dissolved in 15 mL of TFA, and TsOH (0.6 equiv.) and TFAA (trifluoroacetic anhydride, 3.0 equiv.) were sequentially added thereto with stirring at room temperature, and the mixture was heated to 90°C and reacted overnight. After the reaction was completed, silica gel was added to the reaction mixture, and column chromatography was performed to separate and purify the product, thereby obtaining compound 115-4 (0.5 g, yield 47%) as a white solid.

[0205] (4) Compound 115-4 (0.5 g) was dissolved in 20 mL of ethanol, and an aqueous NaOH solution (2.5 equiv.) was added thereto with stirring in an ice water bath, and the mixture was reacted at room temperature for 3 h. After the reaction was completed, the reaction was quenched by adding dilute hydrochloric acid, and ethanol was distilled off. Water was added to dilute the reaction mixture, and the reaction mixture was extracted with EA three times. The organic layers were combined and washed with saturated brine, and the organic layer was concentrated to obtain a crude product of compound 115-5.

[0206] (5) The crude product of compound 115-5 was dissolved in 15 mL of TFA, and TsOH (0.6 equiv.) and TFAA (3.0 equiv.) were sequentially added thereto with stirring at room temperature, and the mixture was heated to 90°C and reacted overnight. After the reaction was completed, silica gel was added to the reaction mixture, and column chromatography was performed to separate and purify the product, thereby obtaining compound 115-6 (0.4 g, yield 86%) as a white solid.

[0207] (6) Compound 115-6 (0.4 g) was dissolved in 20 mL of DCM, and Et3N (3.0 equiv.), HATU (1.2 equiv.) and 3-6 (0.21 g) were added successively under stirring at room temperature. The reaction was allowed to proceed at room temperature for 3 h. After the reaction was completed, the reaction solution was extracted with DCM three times, and the organic phase was combined and washed with dilute hydrochloric acid. The organic phase was concentrated, and silica gel was added to the sample, which was separated and purified by column chromatography to obtain compound 115 (240 mg, yield 35%) as a white solid.

[0208] 13. Synthesis of compound 154

[0209] Compound 154-1 (500.0 mg, 1.7 mmol) was weighed and dissolved in 1,4-dioxane, and compound 3-7 (688.5 mg, 1.7 mmol), potassium carbonate (713.8 mg, 5.1 mmol) and bis-triphenylphosphine palladium dichloride (69.4 mg, 0.085 mmol) were added. The system was replaced with nitrogen three times, and the temperature was raised to 100°C for overnight reaction. The reaction was monitored by LCMS. The positive phase was purified after concentration to obtain compound 154 (light yellow solid, 400.0 mg, yield 47.6%).

[0210] 14. Synthesis of compound 155

[0211] (1) Compound 154 (330.0 mg, 0.68 mmol) was weighed and dissolved in a mixed solvent of tetrahydrofuran and water, and sodium hydroxide (55.0 mg, 1.35 mmol) was added under ice bath. The reaction was allowed to proceed at room temperature for 2 h. The reaction was monitored by LCMS. The system was poured into water, and extracted with ethyl acetate. The aqueous phase was adjusted to be acidic, and extracted with ethyl acetate again to obtain compound 155-1 (white solid, 250.0 mg, yield 78.1%).

[0212] (2) Compound 155-1 (250.0 mg, 0.53 mmol) was weighed and dissolved in DCM, and tert-butyl alcohol (370.6 mg, 0.79 mmol), EDCI (304.8 mg, 1.59 mmol) and DMAP (193.0 mg, 1.58 mmol) were added at room temperature. The reaction was allowed to proceed at room temperature overnight. The next day, the reaction was monitored by LCMS. Water was added to the system, and extracted with dichloromethane. The organic phase was concentrated and purified by positive phase to obtain compound 155 (white oil, 120.0 mg, yield 42.8%).

[0213] 15. Synthesis of compound 180

[0214] Compound 180-1 (500.0 mg, 1.5 mmol) was dissolved in a mixture of 1,4-dioxane and water, and compound 3-7 (612.1 mg, 1.5 mmol), potassium carbonate (621.0 mg, 4.5 mmol), and Pd(dppf)Cl2CH2Cl2(61.2 mg, 0.075 mmol) were added. The system was replaced with nitrogen three times, and then the temperature was raised to 100 °C. The reaction was allowed to proceed overnight. LCMS was used to monitor the completion of the reaction. The positive phase was used for purification after concentration, and compound 180 (white solid, 60.0 mg, yield 52.5%) was obtained.

[0215] 16. Synthesis of compound 179

[0216] Compound 180 (340.0 mg, 0.64 mmol) was dissolved in a mixture of tetrahydrofuran and water, and LiOH (51.0 mg, 1.28 mmol) was added under ice bath. The reaction was allowed to proceed at room temperature for 2 hours. LCMS was used to monitor the completion of the reaction. The system was poured into water, and ethyl acetate was used for extraction. The aqueous phase was adjusted to be acidic, and then ethyl acetate was used for extraction. Compound 179 (white solid, 280.0 mg, yield 85.3%) was obtained.

[0217] 17. Synthesis of compound 181

[0218] Compound 179 (120.0 mg, 0.23 mmol) was dissolved in DMF, and then compound potassium carbonate (95.2 mg, 0.69 mmol) and 2-iodopropane (47.3 mg, 0.28 mmol) were added. The reaction was allowed to proceed at 40 °C for 4 hours. LCMS was used to monitor the completion of the reaction. The system was poured into water, and ethyl acetate was used for extraction. The organic phase was washed with saturated brine 4-5 times, and then concentrated. Compound 181 (white solid, 50.0 mg, yield 30.8%) was obtained after positive phase purification.

[0219] 18. Synthesis of compound 182

[0220] Compound 179 (130.0 mg, 0.3 mmol) was dissolved in a mixture of tert-butyl alcohol and tetrahydrofuran, and DMAP (35.6 mg, 0.3 mmol) and Boc2O (98.1 mg, 0.45 mmol) were added. The reaction was allowed to proceed at room temperature for 2 hours. LCMS was used to monitor the completion of the reaction. The system was poured into water, and ethyl acetate was used for extraction. Compound 182 (white solid, 50.0 mg, yield 45.0%) was obtained.

[0221] 19. Synthesis of compound 215

[0222] (1) Refer to the synthesis method of compound 3-7. Compound 215-1 (300 mg) was dissolved in 10 mL of DMF, and compound 215-2 (1.0 equiv.) and K2CO3 (3.0 equiv.) were sequentially added under stirring at room temperature, and the temperature was increased to 80°C for reaction for 4 h. After the reaction was completed, the reaction solution was extracted with EA for three times, the organic phase was combined, and the organic phase was washed with saturated brine. The organic phase was concentrated to obtain white solid compound 215-3 (140 mg, yield 35%).

[0223] (2) Compound 215-3 (140 mg) was dissolved in 9 mL of ethanol and 3 mL of water, and methoxyamine hydrochloride (2.0 equiv.) was added for reaction at room temperature for 1 h. After the reaction was completed, saturated sodium bicarbonate aqueous solution was added for dilution, the reaction solution was extracted with EA for three times, the organic phase was combined, and the organic phase was washed with saturated brine and then concentrated to obtain white solid compound 215 (90 mg, yield 61%).

[0224] 20, Synthesis of compound 217

[0225] Compound 215-1 (100 mg, 0.28 mmol) was dissolved in DMF (5 mL) at room temperature, and compound 217-1 (37 mg, 0.33 mmol) and potassium carbonate (116 mg, 0.84 mmol) were sequentially added. After addition, the system was stirred at 80°C overnight. After the reaction was completed, EA was added, and the system was washed with water for three times. The organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by normal phase purification to obtain compound 217 (white solid, 95 mg, yield 78%).

[0226] 21, Synthesis of compound 220

[0227] (1) Compound 3-3 (1 g, 4.9 mmol), 220-1 (1 eq), DIAD (3 eq), and PPh3 (3 eq) were dissolved in 10 mL of THF, and the system was reacted at room temperature. After the reaction was completed, the system was extracted with EA and water, the aqueous phase was extracted with EA for two times, the organic phase was combined, washed with saturated brine for three times, dried, and concentrated to obtain 220-2 (818 mg, yield 51%).

[0228] (2) Compound 220-2 (816 mg, 2.4 mmol) and NaOH (3 eq) were dissolved in 5 mL of a mixed solution of ethanol and water, and the system was reacted at room temperature. After the reaction was completed, the system was adjusted to be acidic, extracted with EA and water, and the organic phase was dried and concentrated to obtain product 220-3 (632 mg, yield 85%).

[0229] (3) Compound 220-3 (632 g, 2 mmol), 3-6 (1 eq), HATU (2 eq) and triethylamine (3 eq) were dissolved in 10 mL of DCM and reacted at room temperature. The reaction was controlled by LCMS and completed. The organic phase was dried and concentrated to obtain white solid compound 220 (450 mg, yield 47%).

[0230] 22. Synthesis of compound 230

[0231] Compound 3-7 (300 mg, 0.7 mmol), 230-1 (1 eq) and K2CO3 (3 eq) were dissolved in 5 mL of DMF and reacted at 80°C. The reaction was controlled by LCMS and completed. The reaction system was cooled to room temperature, extracted with EA and water, and the organic phase was dried and concentrated. The sample was mixed with silica gel and purified by normal phase to obtain yellow solid compound 230 (230 mg, yield 63%).

[0232] 23. Synthesis of compound 231

[0233] Compound 3-7 (100 mg) was dissolved in 10 mL of DMF, and potassium carbonate (2.0 equiv) and compound 231-1 (1.0 equiv) were added in turn under stirring at room temperature. The reaction was carried out at room temperature for 1 h. After the reaction was completed, the reaction liquid was extracted with EA three times, the organic phase was combined, and the organic phase was washed with saturated brine and concentrated. The sample was mixed with silica gel and separated and purified by column chromatography to obtain light yellow solid compound 231 (85 mg, yield 75%).

[0234] 24. Synthesis of compound 232

[0235] Compound 231 (100 mg) was dissolved in 10 mL of acetonitrile, and CuBr (2.0 equiv.), CuBr2 (2.0 equiv.) and tert-butyl nitrite (2.0 equiv.) were added in turn under stirring at room temperature. The reaction was carried out at room temperature for 3 h. After the reaction was completed, the sample was mixed with silica gel and separated and purified by column chromatography to obtain yellow solid compound 232 (60 mg, yield 53%).

[0236] 25. Synthesis of compound 236

[0237] Take compound 215-1 (500.0 mg, 1.39 mmol) dissolved in DMF, add compound 236-1 (350.3 mg, 2.09 mmol) and compound potassium carbonate (575.5 mg, 4.17 mmol), and warm to 60°C overnight. Monitor the reaction by LCMS. Pour the system into water, extract with ethyl acetate, wash the organic phase with saturated brine 4-5 times, concentrate the organic phase, and purify by normal phase to obtain compound 236 (white solid, 320.0 mg, yield 49.4%).

[0238] 26. Synthesis of compound 240

[0239] (1) Take compound 3-7 (500.0 mg, 1.24 mmol) dissolved in ethanol, add compound 240-1 (188.0 mg, 2.48 mmol) at room temperature, and warm to 80°C overnight. Monitor the reaction by LCMS. Concentrate the ethanol of the system to obtain compound 240-2 (white oil, 320.0 mg, yield 64.6%).

[0240] (2) Take compound 240-2 (320.0 mg, 0.8 mmol) dissolved in DMF, add cesium carbonate (780.0 mg, 2.4 mmol) and compound 240-3 (211.2 mg, 0.96 mmol), and warm to 80°C for 2 hours. Monitor the reaction by LCMS. Pour the system into water, extract with ethyl acetate, wash the organic phase with saturated brine 4-5 times, concentrate the organic phase, and purify by normal phase to obtain compound 240 (white oil, 80.0 mg, yield 18.4%).

[0241] 27. Synthesis of compound 245

[0242] Take compound 240 (200.0 mg, 0.37 mmol) dissolved in DCM, add compound m-CPBA (44.0 mg, 0.26 mmol) in an ice bath, and warm to room temperature for 2 hours. Monitor the reaction by LCMS. Add a large amount of dichloromethane to the system, then wash with saturated sodium thiosulfate 2-3 times, wash with saturated sodium bicarbonate 4-5 times, concentrate the organic phase, and purify by normal phase to obtain compound 245 (white solid, 55.0 mg, yield 26.7%).

[0243] 28. Synthesis of compound 253

[0244] (1) Compound 3-7 (300 mg) was dissolved in 10 mL of DMF, and potassium carbonate (2.0 equiv) and compound 253-1 (1.0 equiv) were added in turn under stirring at room temperature, and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction solution was extracted with EA three times, the organic phases were combined, and the organic phase was washed with saturated brine and then concentrated. The silica gel was added to the mixture, and column chromatography was performed to separate and purify the mixture to obtain white solid compound 253-2 (310 mg, yield 93%).

[0245] (2) Compound 253-2 was dissolved in 10 mL of DCM, and 10 mL of hydrochloric acid dioxane solution was added under stirring at room temperature, and the mixture was reacted at room temperature for 1.5 h. After the reaction was completed, yellow solid 253-3 (275 mg, yield 97%) was obtained by filtration.

[0246] (3) Compound 253-3 was dissolved in 15 mL of ethanol, and Et3N (2.0 equiv.) and Ac2O (1.5 equiv.) were added in turn under stirring at room temperature, and the mixture was reacted at room temperature for 2 h. After the reaction was completed, the silica gel was added to the mixture, and column chromatography was performed to separate and purify the mixture to obtain yellow solid compound 253 (190 mg, yield 63%).

[0247] Biological activity evaluation (acaricidal activity test)

[0248] The prepared peanut leaf dishes were placed in a covered petri dish, sprayed using a spray tower, and after the spraying was completed, the petri dish cover was opened and completely dried at room temperature. The test insects in a physiological state were selected, and introduced into the center of the leaf dish. Fifteen test insects growing in a consistent manner were introduced into each leaf dish, and the process was repeated three times.

[0249] Each dose was repeated three times, and the same content of acetone was used as a control. After the application, the test insects were transferred to a feeding condition. The number of dead insects after 48 h was checked, and the mortality rate was calculated according to the formula: mortality rate (%) = (number of dead insects / number of test insects) * 100. The representative experimental results are shown in Table 3.

[0250] Table 3: Results of acaricidal activity test Note: N represents no data; Control compound A: Control compound B:

[0251] The compounds described in the present application have satisfactory insecticidal and / or acaricidal activity against animal pests, particularly when applied at a relatively low application rate, and have high selectivity and improved compatibility in useful plant crops.

Claims

1. A substituted aryl amide compound as shown in general formula I, or a salt thereof: in, M represents CR9 or N; W represents O or S; R1, R2, R3, R4, R5, R6, R7, R8, and R9 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyano, nitro, and -OR, respectively. 21 -S(O) m R 21 -N(R) 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 2. Cycloalkyl, cycloalkenyl, aryl, or heterocyclic groups; Or R1 and R2, R3 and R4, R5 and R6, or R7 and R8 together form =O; Alternatively, R3 and R7, R1 and R5, R3 and R5, or R1 and R7 together can form C1-C6 alkylene groups; R 11 R 12 R 13 R 14 R 15 Each of these independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, and -OR. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 )2、-NR 22 (CO)R 21 -NR 22 SO2R 21 , Cycloalkyl, cycloalkenyl, aryl, or heterocyclic groups, wherein the alkyl, alkenyl, or alkynyl group is optionally selected from halogens, cycloalkyl, aryl, heterocyclic groups, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced; R 16 Represents halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -OR 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 2. Cycloalkyl, cycloalkenyl, aryl, or heterocyclic groups, wherein the alkyl, alkenyl, or alkynyl group is optionally selected from halogen, cyano, trialkylsilyl, cycloalkyl, aryl, heterocyclic, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced; R 22 Each of these groups independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic, and -OR. 21 -(CO)R 21 -(CO)OR 21 ,-alkylene-(CO)OR 21 -(SO2)R 21 -(SO2)OR 21 ,-alkylene-(SO2)R 21 -(CO)N(R) 21 )2 or -(SO2)N(R 26 )2; R 21 R 23 Each of these groups independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, or heterocyclic groups, wherein the alkyl, alkenyl, or alkynyl group is optionally selected from halogen, cyano, cycloalkyl, cycloalkenyl, aryl, heterocyclic, -OR 27 -SR 27 -O(CO)R 27 -(CO)R 27 -(CO)N(R) 27 2. -(CO)OR 27 OR-O(CO)OR 27 At least one group in it is replaced; R 24 R 25 Each of these independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl; or CR 24 R 25 Together they form unsubstituted or substituted ring structures; R 26 Each of these can independently represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl. R 27 Each of the following groups independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, phenyl, or phenyl substituted with at least one of the following groups: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl, or phenoxy substituted with at least one of the following groups: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, or haloalkoxy. The aforementioned cycloalkyl, cycloalkenyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, haloalkyl, haloalkenyl, haloynyl, cycloalkyl, halocycloalkyl, alkyl-substituted cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylynyl, unsubstituted or aryl, arylalkyl, heterocyclic, or heterocyclic alkyl groups substituted with at least one of the groups selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy. 10 , -O(CO)OR 10 -SR 10 , -(CO)R 10 -(CO)OR 10 , -(CO)N(R 10 )2,-(CS)N(R 10 )2,-(SO)R 10 -(SO2)R 10 , -N(R 10 )2, -alkylene-OR 10 ,-alkylene-SR 10 ,-alkylene-(CO)R 10 ,-alkylene-(CO)OR 10 ,-alkylene-(CO)N(R) 10 )2,-alkylene-(CS)N(R 10 )2,-alkylene-(SO)R 10 ,-alkylene-(SO2)R 10 ,-alkylene-N(R) 10 )2,-O-alkylene-(CO)OR 10 ,-halogenated alkylene-OR 10 ,-halogenated alkylene-SR 10 ,-halogenated alkylene-(CO)R 10 ,-halogenated alkylene-(CO)OR 10 ,-Halogenide-(CO)N(R 10 )2,-Halogenide-(CS)N(R 10 )2,-Halogenide-(SO)R 10 ,-Halogenide-(SO2)R 10 ,-Halogenide-N(R) 10 )2 or -O-haloalkylene-(CO)OR 10 At least one group in the ring is substituted; or two adjacent carbon atoms on the ring are substituted with an unsubstituted group or a group selected from halogens or -(CO)OR. 10 The -OCH2CH2-, -CH2CH2CH2-, or -OCH2O- group is substituted to form a fused ring; m represents 0, 1, or 2; R 10 Each is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, or aryl or heterocyclic group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The substituted aryl amide compound or its salt according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, cyano, nitro, and -OR, respectively. 21 -S(O) m R 21 -N(R) 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 2. C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclic groups; Or R1 and R2, R3 and R4, R5 and R6, or R7 and R8 together form =O; Alternatively, R3 and R7, R1 and R5, R3 and R5, or R1 and R7 together can form C1-C6 alkylene groups; R 11 R 12 R 13 R 14 R 15 Each of these independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, and -OR. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 )2、-NR 22 (CO)R 21 -NR 22 SO2R 21 , C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclic, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced; R 16 Represents halogens, C1-C8 alkyl groups, C2-C8 alkenyl groups, C2-C8 alkynyl groups, cyano groups, nitro groups, and -OR groups. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 2. C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group is optionally selected from halogen, cyano, triC1-C8 alkylsilyl, C3-C8 cycloalkyl, aryl, heterocyclic, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced; R 22 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic, and -OR. 21 -(CO)R 21 -(CO)OR 21 -(C1-C8 alkylene)-(CO)OR 21 -(SO2)R 21 -(SO2)OR 21 -(C1-C8 alkylene)-(SO2)R 21 -(CO)N(R) 21 )2 or -(SO2)N(R 26 )2; R 21 R 23 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl groups are optionally selected from halogen, cyano, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic, and -OR groups. 27 -SR 27 -O(CO)R 27 -(CO)R 27 -(CO)N(R) 27 2. -(CO)OR 27 OR-O(CO)OR 27 At least one group in it is replaced; R 24 R 25 Each of these independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heterocyclic or heterocyclic-C1-C8 alkyl; or CR 24 R 25 Together they form a 5- to 8-membered carbon ring or a heterocycle containing oxygen, sulfur, or nitrogen; the "5- to 8-membered carbon ring or a heterocycle containing oxygen, sulfur, or nitrogen" is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl, or C1-C8 haloalkyl. R 26 Each of these can independently represent 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; R 27 Each of the following groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, phenyl, or a phenyl group substituted with at least one of the following groups: halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, or a phenoxy group substituted with at least one of the following groups: halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy. The aforementioned C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, C3-C8 cycloalkyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3 -C8 cycloalkylC2-C8 alkenyl, C3-C8 cycloalkylC2-C8 alkynyl, unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or haloC1-C8 alkoxy, -OR 10 , -O(CO)OR 10 -SR 10 , -(CO)R 10 -(CO)OR 10 , -(CO)N(R 10 )2,-(CS)N(R 10 )2,-(SO)R 10 -(SO2)R 10 , -N(R 10 )2, -(C1-C8 alkylene)-OR 10 ,-(C1-C8 alkylene)-SR 10 ,-(C1-C8 alkylene)-(CO)R 10 , -(C1-C8 alkylene)-(CO)OR 10 , -(C1-C8 alkylene)-(CO)N(R 10 )2,-(C1-C8 alkylene)-(CS)N(R 10 )2,-(C1-C8 alkylene)-(SO)R 10 , -(C1-C8 alkylene)-(SO2)R 10 ,-(C1-C8 alkylene)-N(R 10 )2,-O-(C1-C8 alkylene)-(CO)OR 10 -(halogenated C1-C8 alkylene)-OR 10 ,-(halogenated C1-C8 alkylene)-SR 10 ,-(halogenated C1-C8 alkylene)-(CO)R 10 -(halogenated C1-C8 alkylene)-(CO)OR 10 , -(halogenated C1-C8 alkylene)-(CO)N(R 10 )2,-(halogenated C1-C8 alkylene)-(CS)N(R 10 )2,-(halogenated C1-C8 alkylene)-(SO)R 10 -(halogenated C1-C8 alkylene)-(SO2)R 10 ,-(halogenated C1-C8 alkylene)-N(R 10 )2 or -O-(halogenated C1-C8 alkylene)-(CO)OR 10 At least one group in the ring is substituted; or two adjacent carbon atoms on the ring are substituted with an unsubstituted group or a group selected from halogens or -(CO)OR. 10 The -OCH2CH2-, -CH2CH2CH2-, or -OCH2O- group is substituted to form a fused ring; m represents 0, 1, or 2; R 10 Each of the following is independently hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, or aryl or heterocyclic group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

3. A substituted aryl amide compound or a salt thereof according to claim 1 or 2, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, cyano, nitro, and -OR, respectively. 21 -S(O) m R 21 -N(R) 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 2. C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups; Or R1 and R2, R3 and R4, R5 and R6, or R7 and R8 together form =O; Alternatively, R3 and R7, R1 and R5, R3 and R5, or R1 and R7 together can form C1-C6 alkylene groups; R 11 R 12 R 13 R 14 R 15 Each of these independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, and -OR. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 )2、-NR 22 (CO)R 21 -NR 22 SO2R 21 , C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced; R 16 Represents halogens, C1-C6 alkyl groups, C2-C6 alkenyl groups, C2-C6 alkynyl groups, cyano groups, nitro groups, and -OR groups. 21 -S(O) m R 21 -OS(O) m R 21 -S(O) m N(R 22 )2、-N(R 22 )2、-(CO)R 21 -(CO)OR 21 -O(CO)R 21 -(CO)N(R) 22 )2、-(CS)N(R 22 2. C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is optionally selected from halogen, cyano, triC1-C6 alkylsilyl, C3-C6 cycloalkyl, aryl, heterocyclic, -OR 21 -(CO)OR 21 -S(O) m R 21 or -N(R) 22 At least one group in )2 is replaced; R 22 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic, and -OR. 21 -(CO)R 21 -(CO)OR 21 -(C1-C6 alkylene)-(CO)OR 21 -(SO2)R 21 -(SO2)OR 21 -(C1-C6 alkylene)-(SO2)R 21 -(CO)N(R) 21 )2 or -(SO2)N(R 26 )2; R 21 R 23 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups, wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl groups are optionally selected from halogen, cyano, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic, and -OR groups. 27 -SR 27 -O(CO)R 27 -(CO)R 27 -(CO)N(R) 27 2. -(CO)OR 27 OR-O(CO)OR 27 At least one group in it is replaced; R 24 R 25 Each of these independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heterocyclic or heterocyclic-C1-C6 alkyl; or CR 24 R 25 Together they form 5- to 8-membered saturated carbon rings or The 5-8 quinary saturated carbon ring or It is either unsubstituted or substituted with at least one group selected from oxo, C1-C6 alkyl or C1-C6 haloalkyl; R 26 Each of these can independently represent 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; R 27 Each of the following groups 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 a phenyl group substituted with at least one of the following groups: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, or a phenoxy group substituted with at least one of the following groups: 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, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3 -C6 cycloalkylC2-C6 alkenyl, C3-C6 cycloalkylC2-C6 alkynyl, unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or haloC1-C6 alkoxy, -OR 10 , -O(CO)OR 10 -SR 10 , -(CO)R 10 -(CO)OR 10 , -(CO)N(R 10 )2,-(CS)N(R 10 )2,-(SO)R 10 -(SO2)R 10 , -N(R 10 )2, -(C1-C6 alkylene)-OR 10 ,-(C1-C6 alkylene)-SR 10 ,-(C1-C6 alkylene)-(CO)R 10 , -(C1-C6 alkylene)-(CO)OR 10 , -(C1-C6 alkylene)-(CO)N(R 10 )2,-(C1-C6 alkylene)-(CS)N(R 10 )2,-(C1-C6 alkylene)-(SO)R 10 , -(C1-C6 alkylene)-(SO2)R 10 ,-(C1-C6 alkylene)-N(R 10 )2,-O-(C1-C6 alkylene)-(CO)OR 10 -(halogenated C1-C6 alkylene)-OR 10 ,-(halogenated C1-C6 alkylene)-SR 10 ,-(halogenated C1-C6 alkylene)-(CO)R 10 -(halogenated C1-C6 alkylene)-(CO)OR 10 , -(halogenated C1-C6 alkylene)-(CO)N(R 10 )2,-(halogenated C1-C6 alkylene)-(CS)N(R 10 )2,-(halogenated C1-C6 alkylene)-(SO)R 10 -(halogenated C1-C6 alkylene)-(SO2)R 10 ,-(halogenated C1-C6 alkylene)-N(R 10 )2 or -O-(halogenated C1-C6 alkylene)-(CO)OR 10 At least one group in the ring is substituted; or two adjacent carbon atoms on the ring are substituted with an unsubstituted group or a group selected from halogens or -(CO)OR. 10 The -OCH2CH2-, -CH2CH2CH2-, or -OCH2O- group is substituted to form a fused ring; m represents 0, 1, or 2; R 10 Each of the following is independently 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, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, heterocyclic, or aryl or heterocyclic group substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy; Preferably, the compound is selected from any one of the compounds in Table 1.

4. A method for preparing a substituted aryl amide compound or a salt thereof as described in any one of claims 1-3, characterized in that, Includes the following steps: (1) Prepared by reacting the compound of general formula II or its salt with the compound of general formula III. The reaction equation for compounds represented by general formula I is as follows: Alternatively, (2) compound I can be prepared by substitution or coupling reaction using compound IV as an intermediate. Where P is OH or a halogen, Q1 is a halogen, and other substituents are W, M, R1, R2, R3, R4, R5, R6, R7, R8, R 11 R 12 R 13 R 14 R 15 and R 16 The definition is as described in any one of claims 1-3; Preferably, the reaction (1) is carried out in the presence of a solvent, a condensing agent and a base; more preferably, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU, the base is selected from at least one of an inorganic base or an organic base, and / or the solvent is selected from at least one of an aromatic hydrocarbon (such as benzene, chlorobenzene or toluene), DMF, DMA, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane or ethyl acetate.

5. A mite-killing composition, characterized in that, It contains at least one of the substituted aryl amide compounds or their salts as described in any one of claims 1-3 in a biologically effective amount; preferably, it also includes a formulation adjuvant; more preferably, it also includes other active ingredients.

6. A method for preventing and controlling mites, characterized in that, The composition includes a biologically effective amount of the substituted aryl amide compound or its salt as described in any one of claims 1-3, or the composition as described in claim 5, which exposes the mite or its environment to biologically effective amounts.

7. Use of the substituted arylamide compound or its salt as described in any one of claims 1-3, or the composition as described in claim 5, in the control of mites.

8. An intermediate as described in formula II, III or IV of claim 4.

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