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WO2025261261A1 - Composé arylamide substitué ou sel de celui-ci, son procédé de préparation, composition le comprenant et utilisation associée - Google Patents

Composé arylamide substitué ou sel de celui-ci, son procédé de préparation, composition le comprenant et utilisation associée

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Publication number
WO2025261261A1
WO2025261261A1 PCT/CN2025/100810 CN2025100810W WO2025261261A1 WO 2025261261 A1 WO2025261261 A1 WO 2025261261A1 CN 2025100810 W CN2025100810 W CN 2025100810W WO 2025261261 A1 WO2025261261 A1 WO 2025261261A1
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Prior art keywords
alkyl
alkylene
cycloalkyl
alkenyl
aryl
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PCT/CN2025/100810
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English (en)
Chinese (zh)
Inventor
连磊
彭学岗
华荣保
郭翔
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Qingdao Kingagroot Chemical Compound Co Ltd
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Qingdao Kingagroot Chemical Compound Co Ltd
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Publication of WO2025261261A1 publication Critical patent/WO2025261261A1/fr
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Definitions

  • This invention belongs to the field of pesticide technology, specifically relating to a substituted aryl amide compound or its salt, its preparation method, composition and application.
  • This invention provides a substituted aryl amide compound or its salt, a method for preparation, a composition, and an application thereof, wherein the compound has excellent control effects against spider mites such as Tetranychus truncatus and Tetranychus carmineus.
  • R1 , R2 , R3 , R4 , R5 , R6 , R6 , R7 , R8 , and R9 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyano, nitro, -OR21 , -S(O) mR21 , -N( R22 ) 2 , -(CO) R21 , -(CO) OR21 , -O(CO) R21 , -(CO)N( R22 ) 2 , cycloalkyl, cycloalkenyl, aryl, or heterocyclic groups.
  • R1 and R2 , R3 and R4 , R5 and R6 , or R7 and R8 together form O;
  • R3 and R7 , R1 and R5 , R3 and R5 , or R1 and R7 together form C1-C6 alkylene groups
  • R11 , R12 , R13 , R14 , and R15 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -OR21, -S(O) mR21 , -OS(O) mR21 , -S (O) mN ( R22 ) 2 , -N ( R22 ) 2 , -(CO) R21 , -(CO) OR21 , -O(CO) R21 , -(CO)N( R22 ) 2 , -(CS)N( R22 ) 2 , -NR22 (CO) R21 , and -NR22SO2R21 , respectively .
  • 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 substituted by at least one group selected from halogen, cyano, trialkylsilyl, cycloalkyl, aryl, heterocyclic, -OR 21 , -(CO)OR 21 , -S(O) mR 21
  • R 22 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -alkylene-(CO)OR 21 , -(SO 2 )R 21 , -(SO 2 )OR 21 , -alkylene-(SO 2 )R 21 , -(CO)N(R 21 ) 2 or -(SO 2 )N(R 26 ) 2 ;
  • R 21 and R 23 each independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, or heterocyclic groups, wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group 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 ;
  • R 24 and R 25 independently represent hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl; or CR 24 and R 25 together form an unsubstituted or substituted cyclic structure.
  • R 26 can independently represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl.
  • R 27 represents, independently, 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.
  • 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 substituted aryl, arylalkyl, heterocyclic, or heterocyclic alkyl groups selected from at least one of halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy groups, -OR 10 , -O
  • n 0, 1, or 2;
  • R 10 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.
  • R1 , R2 , R3 , R4 , R5 , R6 , 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, -OR21 , -S(O) mR21 , -N( R22 ) 2 , -(CO) R21 , -(CO) OR21 , -O(CO) R21 , -(CO)N( R22 ) 2 , C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclic groups;
  • R1 and R2 , R3 and R4 , R5 and R6 , or R7 and R8 together form O;
  • R3 and R7 , R1 and R5 , R3 and R5 , or R1 and R7 together form C1-C6 alkylene groups
  • R11 , R12 , R13 , R14 , and R15 independently represent hydrogen, halogen, C1-C8 alkyl , C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, -OR21, -S(O)mR21, -OS(O)mR21 , -S ( O) mN ( R22 ) 2 , -N ( R22 ) 2 , -(CO) R21 , -(CO) OR21 , -O(CO) R21 , -(CO)N( R22 ) 2 , -(CS)N( R22 ) 2 , -NR22 (CO) R21 , and -NR22SO2R21 , respectively .
  • the C1-C8 cycloalkyl, C2-C8 cycloalkenyl, aryl, or heterocyclic group wherein the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group is optionally substituted with at least one group selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclic, -OR 21 , -(CO)OR 21 , -S(O) mR 21 , or -N(R 22 ) 2 ;
  • R 16 represents 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 ,
  • R 22 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(C1-C8 alkylene)-(CO)OR 21 , -(SO 2 )R 21 , -(SO 2 )OR 21 , -(C1-C8 alkylene)-(SO 2 )R 21 , -(CO )N(R 21 ) 2 or -(SO 2 )N(R 26 ) 2 ;
  • R 21 and R 23 each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl group is optionally substituted by at least one group selected from halogen, cyano, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic group, -OR 27 , -SR 27 , -O(CO)R 27 , -(CO)R 27 , -(CO)N(R 27 ) 2 , -(CO)OR 27 or -O(CO)OR 27 ;
  • R 24 and R 25 independently represent 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 R 24 and R 25 together 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,
  • R 26 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenylC1-C8 alkyl;
  • R 27 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,
  • 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
  • n 0, 1, or 2;
  • R 10 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,
  • R1 , R2 , R3 , R4 , R5 , R6 , 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, -OR21 , -S(O) mR21 , -N( R22 ) 2 , -(CO) R21 , -(CO) OR21 , -O(CO) R21 , -(CO)N( R22 ) 2 , C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclic groups;
  • R1 and R2 , R3 and R4 , R5 and R6 , or R7 and R8 together form O;
  • R3 and R7 , R1 and R5 , R3 and R5 , or R1 and R7 together form C1-C6 alkylene groups
  • R11 , R12 , R13 , R14 , and R15 independently represent hydrogen, halogen, C1-C6 alkyl , C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, -OR21, -S(O)mR21, -OS(O)mR21 , -S ( O) mN ( R22 ) 2 , -N ( R22 ) 2 , -(CO) R21 , -(CO) OR21 , -O(CO) R21 , -(CO)N( R22 ) 2 , -(CS)N( R22 ) 2 , -NR22 (CO) R21 , and -NR22SO2R21 , respectively .
  • the C1-C6 cycloalkyl, C2-C6 cycloalkenyl, aryl, or heterocyclic group wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally substituted with at least one group selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic, -OR 21 , -(CO)OR 21 , -S(O) mR 21 , or -N(R 22 ) 2 ;
  • R 16 represents halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 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 ,
  • R 22 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(C1-C6 alkylene)-(CO)OR 21 , -(SO 2 )R 21 , -(SO 2 )OR 21 , -(C1-C6 alkylene)-(SO 2 )R 21 , -(CO )N(R 21 ) 2 or -(SO 2 )N(R 26 ) 2 ;
  • R 21 and R 23 each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic group, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group is optionally substituted by at least one group selected from halogen, cyano, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic group, -OR 27 , -SR 27 , -O(CO)R 27 , -(CO)R 27 , -(CO)N(R 27 ) 2 , -(CO)OR 27 or -O(CO)OR 27 ;
  • R 24 and R 25 independently represent 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 R 24 and R 25 together form a 5- to 8-membered saturated carbon ring 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 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C6 alkyl;
  • R 27 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,
  • 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
  • n 0, 1, or 2;
  • R 10 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,
  • alkyl groups having more than two carbon atoms can be straight-chain or branched.
  • alkylene-OR 10 alkylene can be -CH 2- , -CH 2 CH 2- , -CH(CH 3 )-, -C(CH 3 ) 2- , etc.
  • Alkyl groups are, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl.
  • alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl.
  • Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group.
  • Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
  • cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position.
  • Halogens are fluorine, chlorine, bromine, or iodine.
  • aryl in this invention includes, but is not limited to, phenyl, naphthyl, and...
  • heterocyclic group includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups.
  • heteroaryl groups i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example
  • the terms “optional” or “optionally” mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur.
  • the term “optionally...substituted” means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned.
  • the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.
  • the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment.
  • a heteroaryl group substituted by one methyl group. Can represent wait.
  • the present invention also includes any ketone and enol tautomer forms, mixtures thereof, and salts thereof.
  • the method for preparing the substituted aryl amide compound or its salt includes the following steps:
  • (2) compound I can be prepared by substitution or coupling reaction using compound IV as an intermediate.
  • 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 inorganic bases (such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, Cs2CO3 , KF , CsF , etc.) or organic bases (such as pyrazole, triethylamine, N,N-diisopropylethylamine, pyridine, DIEA, potassium trimethylsilanol, AcOK, AcONa, MeONa, EtONa, t-BuONa, t-BuOK, etc.); the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene, or toluene), DMF, DMA,
  • acaricide composition comprising a biologically effective amount of at least one of the aforementioned substituted arylamide compounds or their salts; preferably, it further comprises a formulation adjuvant; more preferably, it further comprises other active ingredients.
  • This application also discloses a method for controlling mites, comprising exposing the mites or their environment to a biologically effective amount of the aforementioned substituted aryl amide compound or its salt or the aforementioned combination.
  • This application also discloses the use of an arylamide compound or its salt or composition as described above in the control of mites.
  • This application also discloses an intermediate, as shown in Formulas II, III or IV above.
  • Salts of the compounds suitable for use according to the present invention are conventional, non-toxic salts, preferably agriculturally and/or physiologically acceptable salts.
  • Salts with inorganic bases are preferred, such as alkali metal salts (e.g., sodium, potassium, or cesium salts), alkaline earth metal salts (e.g., calcium or magnesium salts), ammonium salts; or salts with organic bases, particularly organic amines, such as triethylammonium salts, dicyclohexylammonium salts, N,N'-dibenzylethylidene diammonium salts, pyridinium salts, methylpyridinium salts, or ammonium ethanolate salts; salts with inorganic acids (e.g., hydrochlorides, hydrobromates, dihydrogen sulfates, trihydrogen sulfates, or phosphates); and salts with organic carboxylic acids or organic s
  • alkali metal salts e.
  • compounds of Formula I can exist as geometrically and/or optically active isomers or mixtures of corresponding isomers with different compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, transisomers, or geometric isomers. Therefore, the present invention includes pure stereoisomers and any mixtures of these isomers.
  • the active compounds of this invention due to their combination of good plant tolerance, beneficial toxicity to warm-blooded animals, and good environmental tolerance, are suitable for protecting plants and plant organs, increasing yield, improving the quality of harvested products, and controlling animal pests, particularly insects, arachnids, worms, nematodes, and mollusks encountered in agriculture, horticulture, animal husbandry, forestry, parks and recreational facilities, protection of stored products and materials, and in the health sector. They are preferably used as plant protectants. They are active against generally susceptible and resistant species and at all or some developmental stages.
  • the aforementioned pests include:
  • Anoplura includes genera such as Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., and Trichodectes spp.
  • Arachnida for example, *Acarus spp.*, *Aceria sheldoni*, *Aculops spp.*, *Aculus spp.*, *Amblyomma spp.*, *Amphitertranychus viennensis*, *Argas spp.*, *Boophilus spp.*, *Brevipalpus spp.*, and *B. cloverleaf*.
  • Bivalva for example, Dreissena spp.
  • Chilopoda for example, the genera *Geophilus* spp. and *Scutigera* spp.
  • Coleoptera for example: *Acalymma vittatum*, *Acanthoscelides obtectus*, *Adoretus* spp., *Agelastica alni*, *Agriotes* spp., *Amphimallon solstitialis*, *Anobium punctatum*, *Anoplophora* spp., *Anthonomus* spp., and others.
  • Diplopoda for example, Blaniulus guttulatus.
  • Diptera for example, genera such as Aedes spp., Agromyza spp., Anastrea spp., Anopheles spp., Asphondylia spp., Bactrocera spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitalia, and Chiron.
  • Gastropoda for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., and Succinea spp.
  • Helminths for example, *Ancylostoma duodenale*, *Ancylostoma ceylanicum*, *Acylostoma braziliensis*, *Ancylostoma* spp., *Ascaris lubricoides*, *Ascaris* spp., *Brugia malayi*, *Brugia timori*, *Bunostomum* spp., *Chabertia* spp., and *Clonorchis* spp.
  • Heteroptera for example, the pumpkin stink bug (Anasa tristis), the genus *Antestiopsis*, the genus *Blissus*, the genus *Calocoris*, *Campylomma livida*, the genus *Cavelerius*, the genus *Cimex*, the genus *Collaria*, and the genus *Creontiades*.
  • Homoptera including genera such as *Acyrthosipon* spp., *Acrogonia* spp., *Aeneolamia* spp., *Agonoscena* spp., *Aleurodes* spp., *Aleurolobus barodensis*, *Aleurothrixus* spp., *Amrasca* spp., *Anuraphis cardui*, *Aonidiella* spp., *Aphanostigma piri*, *Aphis* spp., *Arboridia apicalis*, and *Aspidiella* spp.
  • Hymenoptera for example, Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, and Vespa spp.
  • Isopoda for example, woodlice (Armadillidium vulgare), comb beetles (Oniscus acelus), and ball beetles (Porcellio scaber).
  • Isoptera for example, Acromyrmex spp., Atta spp., Cornitermes cumulans, Microtermes obesi, Odontotermes spp., and Reticulitermes spp.
  • 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*, and *Bupalus piniarius*.
  • Cydia spp. (Coptirsia 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., 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*,
  • Orthoptera for example, house cricket (Acheta domesticus), oriental cockroach (Blatta orientalis), German cockroach (Blattella germanica), Dichroplus spp., mole cricket (Gryllotalpa spp.), Madeira cockroach (Leucophaea maderae), migratory locust (Locusta spp.), black locust (Melanoplus spp.), American cockroach (Periplaneta americana), and desert locust (Schistocerca gregaria).
  • Siphonaptera for example, the genera *Ceratophyllus* spp. and *Xenopsylla cheopis*.
  • Synphyla for example, Scutigerella spp.
  • Thysanoptera including species such as the yellow corn thrips (Anaphothrips obscures), rice thrips (Baliothrips biformis), grape thrips (Drepanothris reuteri), Enneothrips flavens, flower thrips (Frankliniella spp.), netted thrips (Heliothrips spp.), greenhouse hedge thrips (Hercinothrips femoralis), grape thrips (Rhipiphorothrips cruentatus), hard thrips (Scirtothrips spp.), Taeniothrips cardamoni, and thrips (Thrips spp.).
  • Thysanura for example, silverfish (Lepisma saccharina).
  • Plant-parasitic nematodes include, for example, genera such as *Aphelenchoides* spp., *Bursaphelenchus* spp., *Ditylenchus* spp., *Globodera* spp., *Heterodera* spp., *Longidorus* spp., *Meloidogyne* spp., *Pratylenchus* spp., *Radipoholus similis*, *Trichodorus* spp., *Tylenchulus semipenetrans*, and *Xiphinema* spp.
  • the active compound complexes of the present invention can also be used at certain concentrations or application rates as herbicides, safeners, growth regulators, or agents for improving plant characteristics, or as antimicrobial agents, such as fungicides, antifungals, bactericides, antivirals (including agents resistant to viroids), or as agents resistant to MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.
  • the present invention also relates to formulations comprising at least one active compound of the present invention and forms of use prepared from these formulations as crop protection compositions and/or insecticides, such as infiltration, dripping, and spraying solutions.
  • These forms of use optionally include other crop protectants and/or insecticides and/or adjuvants that enhance activity, such as penetrants, such as vegetable oils (e.g., rapeseed oil, sunflower oil), mineral oils (e.g., paraffin oil), alkyl esters of vegetable fatty acids (e.g., rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates, and/or spreaders such as alkylsiloxanes and/or salts, such as organic or inorganic ammonium or phosphonium salts (e.g., ammonium sulfate or diammonium hydrogen phosphate), and/or retention promoters such as dioctyl sulfosuccinate
  • formulations include, 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 pesticide specifications, the FAO manual on development and use of FAO, and WHO specifications for pesticides, FAO Plant Production and Protection Papers-173, 2004, ISBN: 9251048576, prepared by the FAO/WHO Joint Meeting on Pesticide Specification.
  • the formulations optionally contain other agrochemically active compounds.
  • Preferred formulations or uses include adjuvants (e.g., fillers, solvents, spontaneous accelerators, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners, and/or other adjuvants, such as adjuvants).
  • adjuvants are components that enhance the biological effect of the formulation, while the components themselves do not have a biological effect.
  • examples of adjuvants are agents that promote retention, dispersibility, adhesion to leaf surfaces, or penetration.
  • formulations are prepared in a known manner, such as by mixing an active compound with adjuvants, such as fillers, solvents, and/or solid carriers, and/or other adjuvants such as surfactants. These formulations are prepared in a suitable apparatus or before or during use.
  • adjuvants such as fillers, solvents, and/or solid carriers, and/or other adjuvants such as surfactants.
  • Substances used as adjuvants are suitable for imparting specific properties, such as certain physical, technological and/or biological properties, to active compound formulations and/or application forms derived therefrom (e.g., ready-to-use crop protection compositions, such as sprays or seed dressings).
  • Suitable fillers are, for example, water, polar and nonpolar organic chemical liquids such as aromatic and non-aromatic hydrocarbons (e.g., paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene), alcohols and polyols (which may also be substituted, etherified and/or esterified if appropriate), ketones (e.g., acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (e.g., N-alkylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide).
  • aromatic and non-aromatic hydrocarbons e.g., paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene
  • alcohols and polyols which may also be substituted
  • Suitable liquid solvents include: aromatic compounds, such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as petroleum fractions, mineral oils, and vegetable oils; alcohols, such as butanol or ethylene glycol, and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; highly polar solvents, such as dimethylformamide and dimethyl sulfoxide; and water.
  • aromatic compounds such as xylene, toluene, or alkylnaphthalene
  • chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, or dichloromethane
  • suitable solvents include aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons such as cyclohexane, paraffin, petroleum fractions, mineral oils, and vegetable oils; alcohols such as methanol, ethanol, isopropanol, butanol, or ethylene 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 water.
  • aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalene
  • chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride,
  • Suitable carriers include, in particular, ammonium salts and pulverized natural minerals such as kaolin, clay, talc, chalk, quartz, palygorskite, montmorillonite, or diatomaceous earth, as well as pulverized synthetic minerals such as highly dispersed silica, alumina, and natural and synthetic silicates, resins, waxes, and/or solid fertilizers. Mixtures of the aforementioned carriers may also be used.
  • Solid carriers suitable for granules include, for example, pulverized and graded natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, as well as synthetic granules of inorganic and organic powders and granules of organic materials such as sawdust, paper, coconut husks, corn cobs, and tobacco stalks.
  • Liquefied gas fillers or solvents can also be used.
  • Particularly suitable fillers or carriers are those that are gaseous at room temperature and atmospheric pressure, such as aerosol jets, halogenated hydrocarbons, and butane, propane, nitrogen, and carbon dioxide.
  • emulsifiers and/or foaming agents examples include salts of polyacrylates, lignin sulfonates, phenol sulfonic acids or naphthalene sulfonic acids, 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 sulfosuccinates, taurine derivatives (e.g., alkyl taurates), phosphate esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulfates, sulfonates and phosphates, such as alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates,
  • adjuvants that may be present in formulations and in forms of use derived from said formulations include dyes, such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue; and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes; and nutrients and micronutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.
  • dyes such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue
  • organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes
  • nutrients and micronutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.
  • Other components may be stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers, or other agents that enhance chemical and/or physical stability. Foaming agents or defoamers may also be present.
  • Thickening agents such as carboxymethyl cellulose, may also be present in the formulation and in the form of use derived from said formulation as other adjuvants; and natural and synthetic polymers in powder, granule, or latex form, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate; or other natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids.
  • Other possible adjuvants include mineral oils and vegetable oils.
  • adjuvants may also be present in the formulation and in forms of use derived from the formulation.
  • additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention enhancers, stabilizers, chelating agents, complexing agents, wetting agents, and spreading agents.
  • the active compound can be combined with any solid or liquid additive commonly used for formulation purposes.
  • Useful retention enhancers include all those substances that reduce dynamic surface tension, such as dioctyl sulfosuccinate; or substances that improve viscoelasticity, such as hydroxypropyl guar polymer.
  • a useful penetrant refers to all substances commonly used to enhance the penetration of agriculturally active compounds into plants.
  • a penetrant is defined by its ability to penetrate from (typically aqueous) application solutions and/or spray coatings into the plant epidermis and thus enhance the mobility of the active compound within the epidermis.
  • alkanolates such as coconut oil fatty acid ethoxylate (10) or isotracene ethoxylate (12); fatty acid esters, such as rapeseed oil methyl ester or soybean oil methyl ester; fatty amines, such as tallow amine ethoxylate (15); or ammonium and/or phosphonium salts, such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulation contains preferably 0.00000001 to 98% by weight of an active ingredient, more preferably 0.01% to 95% by weight, and even more preferably 0.5% to 90% by weight, based on the weight of the formulation.
  • the content of active ingredient in the application form (crop protection composition) prepared from the formulation can vary within a wide range.
  • the concentration of active ingredient in the application form can typically be from 0.00000001 to 95% by weight, preferably from 0.00001 to 1% by weight, based on the weight of the application form.
  • Application is carried out in a conventional manner suitable for the application form.
  • the active compounds of the present invention can be used on their own or in formulations comprising mixtures with one or more suitable fungicides, bactericides, acaricides, nematicides, insecticides, microbial agents, fertilizers, attractants, sterilizers, synergists, safeners, chemical pheromones, and/or plant growth regulators, for the purpose of, for example, broadening the activity spectrum, prolonging the duration of action, increasing the rate of action, preventing rejection, or preventing the development of resistance.
  • plant growth can be improved through these conjugates, which can improve tolerance to abiotic stresses, such as increasing tolerance to high or low temperatures, increasing tolerance to drought, or to salinity in water and/or soil.
  • the active compounds of the present invention can also improve the quality of flowering and fruiting, optimize germination performance and root development, facilitate harvesting and increase yield, accelerate ripening, improve the quality and/or nutritional value of harvested products, extend the shelf life of harvested products, and/or improve their processing properties.
  • the active compounds of the present invention as well as the combination of common components, produce a synergistic effect; that is, the potency of the mixture is greater than that of the individual components.
  • the compound can typically be used in the form of premix, tank mix, or freshly prepared mixture, and can also be used in seed application.
  • the active compounds referred to here by their common names are known and described, for example, in the Pesticide Manual (14th edition, British Crop Protection Council 2006), or can be found online (e.g., http://www.alanwood.net/pesticide).
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, for example, alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, and chlorfenapyr. (formetanate), furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb;
  • AChE Acetylcholinesterase
  • organophosphates such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, and diazinon.
  • GABA-controlled chloride channel antagonists such as cyclopentadiene organochlorines, for example, chlordane and endosulfan;
  • phenylpyrazoles such as ethiprole and fipronil.
  • Sodium channel modulators/potential-dependent sodium channel blockers such as pyrethroids, including acrinathrin, allethrin, d-cis-transallethrin, d-transallethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, and cyfluthrin.
  • Nicotinic acetylcholine receptor (nAChR) agonists such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.
  • nAChR Nicotinic acetylcholine receptor
  • Nicotinic acetylcholine receptor (nAChR) allosteric activators such as spinosomycins, such as spintoram and spinosad.
  • Chloride channel activators such as avermectins/milbemycins, for example abamectin, emamectin-benzoate, lepimectin, and milbemycin.
  • Juvenile hormone analogues such as hydroprene, kinoprene, methoprene; or fenoxycarb; or pyriproxifen.
  • Active substances with unknown or non-specific mechanisms of action such as haloalkanes, such as bromomethane, other haloalkanes; or chloropicrin; or thiocyanate; or borax; or tartar emetic.
  • haloalkanes such as bromomethane, other haloalkanes; or chloropicrin; or thiocyanate; or borax; or tartar emetic.
  • Mite growth inhibitors such as clofentezine, hexythiazox, diflovidazin; or etoxazole.
  • 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.
  • Oxidative phosphorylation inhibitors such as diafenthiuron; or organotin acaricides, such as azocyclotin, cyhexatin, fenbutatin-oxide; or propargite; or tetradifon.
  • Oxidative phosphorylation uncoupling agents that function through a discontinuous H proton gradient, such as chlorfenapyr, dinitrocresol (DNOC), and sulfluramid.
  • Nicotinic acetylcholine receptor channel blockers such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.
  • Chitin biosynthesis inhibitors type 0, for example, bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
  • Chitin biosynthesis inhibitors type 1, for example, buprofezin.
  • Ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.
  • Octopus aminergic agonists such as amitraz.
  • Acetyl-CoA carboxylase inhibitors such as tetramic acids and their derivatives, such as spirodiclofen, spiromesifen, and spirotetramat.
  • Lanni base receptor modulators such as diamides, such as chlorantraniliprole and flubendiamide.
  • active ingredients with unknown or undetermined mechanisms of action include, for example, amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, cyantraniliprole (cyazypyr), cyflumetofen, dicofol, and diflubenzuron.
  • the active compound of the present invention may also exist in its commercially available formulations and in a form prepared by mixing said formulations with a synergist.
  • the synergist is a compound that can enhance the activity of the active compound; the added synergist itself does not necessarily possess activity.
  • the active compound of the present invention When used as an insecticide, is also available in its commercially available formulations and in use forms prepared by mixing the formulations with an inhibitor that reduces the degradation of the active compound after application to the plant's habitat, on the surface of plant parts, or in plant tissues.
  • plants and plant parts can be processed according to this invention.
  • the term "plant” in this invention should be understood to refer to all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants that can be obtained through conventional breeding and selection methods, or through biotechnology and genetic engineering methods, or a combination of the foregoing, including transgenic plants and cultivated plants, including those protected or unprotected by plant breeders’ rights.
  • Plant parts can be understood to mean all above-ground and underground plant parts and organs, such as buds, leaves, flowers, and roots, examples including leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, seeds, roots, tubers, and rhizomes.
  • the plant parts also include harvested materials, as well as asexual and sexually propagated materials, such as cuttings, tubers, rhizomes, branches, and seeds.
  • the treatment of plants and plant parts using active compounds according to the present invention is achieved by directly applying the compounds to the environment, habitat, or storage space through conventional treatment methods, such as soaking, spraying, evaporation, misting, sowing, smearing, and injection. Furthermore, for propagation materials, especially seeds, one or more layers of coating may be applied.
  • all plants and their parts can be treated according to the invention.
  • wild plant varieties and cultivated plant species, or plant varieties and cultivated plant species obtained by conventional biological breeding methods such as hybridization or protoplast fusion, and their parts are treated.
  • transgenic plants and cultivated plant species (genetically modified organisms) and their parts obtained through genetic engineering, and if appropriate, in combination with conventional methods are treated.
  • the terms "part” or "plant part” are interpreted as above.
  • the plants treated according to the present invention are commercially available or used cultivars.
  • the term "cultivar” is understood to mean a plant with novel characteristics ("features") obtained through conventional breeding, mutagenesis, or recombinant DNA technology. These can be cultivars, biotypes, or genotypes.
  • the treatments of this invention can also produce super-additive (“synergistic”) effects.
  • This can result in effects exceeding conventional expectations, such as reducing the application rate of the compounds and compositions used in this invention and/or broadening their spectrum of action and/or increasing their activity; improving plant growth; increasing tolerance to high or low temperatures; increasing tolerance to drought or salinity in water or soil; improving flowering quality; simplifying harvesting; accelerating maturity; increasing harvest yield; improving the quality of harvested products and/or improving their nutritional value; and improving the storage properties and/or processing performance of harvested products.
  • Preferred transgenic plants or plant cultivars treated according to the present invention include all plants that have received genetic material in genetic modification that imparts particularly advantageous and useful characteristics (“features”) to the plants.
  • features include improved plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to salinity in water or soil, improved flowering quality, easier harvesting, accelerated ripening, increased harvest yield, improved quality and/or nutritional value of harvested products, and improved storage properties and/or processing performance of harvested products.
  • Other examples of such characteristics particularly emphasized, include improved plant resistance to animal and microbial pests, such as resistance to insects, mites, plant pathogenic fungi, bacteria, and/or viruses, and increased plant tolerance to certain herbicidal active compounds.
  • transgenic plants examples include important crop plants such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas, and other vegetable varieties, cotton, tobacco, rapeseed, and fruit plants (fruits such as apples, pears, citrus fruits, and grapes), with particular emphasis on corn, soybeans, potatoes, cotton, tobacco, and rapeseed.
  • the particularly emphasized characteristic is the enhancement of plant resistance to insects, arachnids, nematodes, slugs, and snails through toxins formed within the plant, especially toxins formed within the plant by the genetic material of Bacillus thuringiensis (e.g., genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF, and their combinations; hereinafter referred to as "Bt plants”).
  • Bacillus thuringiensis e.g., genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF, and their combinations; hereinafter referred to as "Bt plants”).
  • the characteristics specifically emphasized are enhanced plant resistance to fungi, bacteria, and viruses through systemically acquired resistance (SAR), systemins, phytoalexins, initiators, resistance genes, and corresponding expressed proteins and toxins. Furthermore, the characteristic specifically emphasized is enhanced plant tolerance to certain herbicidal active compounds such as imidazolinones, sulfonylureas, glyphosate, or phosphinothricin (e.g., the "PAT" gene). Genes conferring the desired characteristics can also coexist in combination within the transgenic plant.
  • An example of a "Bt plant” that can be mentioned is the commercially available brand name YIELD.
  • herbicide-tolerant plants e.g., corn, cotton, soybeans
  • corn e.g., corn
  • cotton e.g., corn
  • An example of a herbicide-tolerant plant that may be mentioned is the commercially available brand Roundup. (Glyphosate tolerant, such as corn, cotton, soybean), Liberty (It has glufosinate tolerance, such as in rapeseed) (with imidazolinone tolerance) and Corn varieties, cotton varieties, and soybean varieties (with sulfonylurea tolerance, such as corn) are examples.
  • Herbicide-resistant plants that may be mentioned include those called... Commercially available varieties (e.g., corn).
  • the above description also applies to plant cultivars with the aforementioned genetic characteristics or genetic characteristics to be developed, which will be developed and/or marketed in the future.
  • the aforementioned plants can be treated, in a particularly advantageous manner, with compounds of general formula I or mixtures of active compounds of the present invention, according to the present invention.
  • the preferred range of the aforementioned active compounds or mixtures also applies to the treatment of the plants. Particular emphasis is placed on the treatment of the plants with compounds or mixtures specifically proposed in this invention.
  • the active compounds of this invention are active not only against harmful substances in plants, hygiene hazards and stored product hazards, but also against animal parasites (external and internal parasites) in the veterinary field, such as hard ticks, soft ticks, scabies mites, spider mites, flies (biting and sucking), parasitic fly larvae, lice, hairy lice, feather lice and fleas.
  • the active compound of Formula I of the present invention is also applicable to the prevention and control of arthropods that infest the following animals: agricultural livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, and bees; other pets, such as dogs, cats, caged birds, and ornamental fish; and laboratory animals, such as hamsters, guinea pigs, rats, and mice.
  • the prevention and control of these arthropods aims to reduce mortality and yield (meat, milk, wool, fur, eggs, honey, etc.), thereby making livestock farming more economical and easier through the use of the active compound of the present invention.
  • the active compounds of the present invention are used in the veterinary field and animal husbandry in known ways, and are administered in the following forms: enteric administration by means of, for example, tablets, capsules, decoctions, veterinary single-dose medications, granules, ointments, pills, feed-through, and suppositories; parenteral administration by means of, for example, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implantation; nasal administration; administration by means of, for example, soaking or bathing, spraying, pouring and dripping, washing and powdering; and dermal administration by means of model articles including the active compounds, such as collars, ear tags, tail tags, limb bands, bridles, markers, etc.
  • the active compound of Formula I can be used directly as a formulation (e.g., powder, emulsion, flowable agent) comprising 1 to 80% by weight of the active compound, or after being diluted 100 to 10,000 times, or in the form of a chemical bath.
  • a formulation e.g., powder, emulsion, flowable agent
  • industrial materials should be understood as inanimate materials, such as, preferably, plastics, adhesives, glues, paper and boards, leather, wood and processed wood products, and coating compositions.
  • the ready-to-use composition may optionally contain other insecticides, and may optionally contain one or more fungicides.
  • the compounds of the present invention can be used to protect objects that come into contact with saltwater or brackish water, particularly ship hulls, screens, nets, buildings, mooring equipment, and signaling systems, from fouling.
  • the compounds of the present invention can be used alone or in combination with other active compounds as antifouling compositions.
  • the active compounds of this invention are also suitable for controlling animal pests, particularly insects, arachnids, and mites found in enclosed spaces such as dwellings, factory workshops, offices, and vehicle cabins, in the protection of household products, hygiene practices, and storage environments. They can be used alone or in combination with other active compounds and adjuvants in household insecticides for controlling these pests. They are effective against both susceptible and resistant species and at all developmental stages.
  • Suitable active compounds such as phosphate esters, carbamates, pyrethroids, neonicotinoids, growth regulators, or active compounds from other known insecticides.
  • aerosols are used in the form of the following products: aerosols, pressure-free spray products such as pump and atomizer sprays, automatic fogging systems, smoke agents, foaming agents, gels, evaporation products with evaporator sheets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propellant-driven evaporators, energy-free or passive evaporation systems, moth traps, moth traps or moth traps, as granules or powders in thrown bait or bait stations.
  • compound 215-1 100 mg, 0.28 mmol was dissolved in DMF (5 mL), followed by the addition of compound 217-1 (37 mg, 0.33 mmol) and potassium carbonate (116 mg, 0.84 mmol). After the addition was complete, the mixture was stirred overnight at 80 °C. After the reaction was complete, EA was added, and the mixture was washed three times with water. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and purified by normal phase mixing to give compound 217 (white solid, 95 mg, 78% yield).
  • the compounds of this invention exhibit satisfactory insecticidal and/or acaricidal activity against animal pests, particularly when applied at relatively low application rates, and demonstrate high selectivity and improved compatibility in useful plant crops.

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  • Hydrogenated Pyridines (AREA)

Abstract

La présente invention relève du domaine technique des pesticides, et concerne en particulier un composé arylamide substitué ou un sel de celui-ci, une composition le comprenant, et une utilisation associée. Le composé est tel que représenté dans la formule générale I, dans laquelle M représente CR9 ou N ; W représente O ou S ; R1, R2, R3, R4, R5, R6, R6, R7, R8 et R9 représentent chacun indépendamment hydrogène, halogène, alkyle, ou similaire ; R11, R12, R13, R14 et R15 représentent chacun indépendamment hydrogène, halogène, alkyle, ou similaire ; et R16 représente halogène, alkyle, alcényle, alcynyle, ou similaire. Le composé a un excellent effet de lutte contre Tetranychus truncatus, Tetranychus cinnabarinus, et analogues.
PCT/CN2025/100810 2024-06-17 2025-06-13 Composé arylamide substitué ou sel de celui-ci, son procédé de préparation, composition le comprenant et utilisation associée Pending WO2025261261A1 (fr)

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CN202410773615 2024-06-17
CN202410773615.1 2024-06-17
CN202510715148.1 2025-05-29
CN202510715148.1A CN121159506A (zh) 2024-06-17 2025-05-29 取代的芳基酰胺化合物或其盐及其制备方法、组合物和应用

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WO2025261261A1 true WO2025261261A1 (fr) 2025-12-26

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WO (1) WO2025261261A1 (fr)

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