Fused bicyclic heterocycle derivatives as pesticides

Abstract

To provide compounds which broaden the spectrum of pesticides and / or improve their activity.SOLUTION: Provided are novel compounds of the formula (I), where Q is selected from Q2, Q3, Q16, and the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention provides novel fused bicyclic heterocyclic derivatives of formula (I), s), especially acaricides and / or miticides for controlling arthropods, especially insects and arachnids The present invention relates to their use as insecticides, as well as to processes and intermediates for their preparation. [Background technology]

[0002] Fused bicyclic heterocyclic derivatives having insecticidal properties are described in the literature, for example, WO2010 / 12598 5, WO2012 / 074135, WO2012 / 086848, WO2013 / 018 928, WO2013 / 191113, WO2014 / 142292, WO2014 / 1 48451, WO2015 / 000715, WO2015 / 121136, WO2015 / 198859, WO2015 / 133603, WO2015 / 198859, WO20 15 / 002211, WO2015 / 071180, WO2015 / 091945, WO 2016 / 005263, WO2015 / 198817, WO2016 / 124563, WO2016 / 124557, WO2016 / 091731, WO2016 / 03944 4, WO2016 / 041819, WO2016 / 039441, WO2016 / 026 848, WO2016 / 023954, WO2016 / 020286, WO2016 / 0 46071, and WO2017 / 072039.

[0003] Modern crop protection compositions are characterized by, for example, their degree, duration and range of action, as well as the possibility Many requirements must be met regarding use: toxicity issues, beneficial species and pollination. The user savings, environmental properties, application rate, and possibility of combination with other active compounds or formulation auxiliaries are The complexity involved in synthesizing active compounds plays a role as well, with only a few parameters For all these reasons alone, new crop protection compositions are becoming increasingly popular. The search for compounds is not considered exhaustive and may be inconsistent with known compounds, at least in terms of individual aspects. There is a continuing need for new compounds with comparatively improved properties. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO2010 / 125985 [Patent Document 2] WO2012 / 074135 [Patent Document 3] WO2012 / 086848 [Patent Document 4] WO2013 / 018928 [Patent Document 5] WO2013 / 191113 [Patent Document 6] WO2014 / 142292 [Patent Document 7] WO2014 / 148451 [Patent Document 8] WO2015 / 000715 [Patent Document 9] WO2015 / 121136 [Patent Document 10] WO2015 / 198859 [Patent Document 11] WO2015 / 133603 [Patent Document 12] WO2015 / 198859 [Patent Document 13] WO2015 / 002211 [Patent Document 14] WO2015 / 071180 [Patent Document 15] WO2015 / 091945 [Patent Document 16] WO2016 / 005263 [Patent Document 17] WO2015 / 198817 [Patent Document 18] WO2016 / 124563 [Patent Document 19] WO2016 / 124557 [Patent Document 20] WO2016 / 091731 [Patent Document 21] WO2016 / 039444 [Patent Document 22] WO2016 / 041819 [Patent Document 23] WO2016 / 039441 [Patent Document 24] WO2016 / 026848 [Patent Document 25] WO2016 / 023954 [Patent Document 26] WO2016 / 020286 [Patent Document 27] WO2016 / 046071 [Patent Document 28] WO2017 / 072039 Summary of the Invention [Problem to be solved by the invention]

[0005] The object of the present invention is to broaden the spectrum of pesticides in various aspects and / or The aim was to provide compounds which improve their activity. [Means for solving the problem]

[0006] Novel fused bicyclic heterocyclic derivatives have now been discovered, which are useful in the synthesis of previously known compounds. have advantages over other products, such as better biological or environmental properties, Wide range of application methods, better insecticidal or acaricidal action, and good compatibility with useful plants Fused bicyclic heterocycle derivatives improve efficacy against particularly difficult-to-control insects. It can be used in combination with additional drugs to

[0007] The subject of the present invention is therefore a compound of formula (I) [ka]

[0008] [In the formula (configuration 1-1), R 1 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6) -cyanoalkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-alkoxy -(C1-C6)-alkyl, (C1-C6)-haloalkoxy-(C1-C6)-al Alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyloxy-(C1-C6 )-alkyl, (C2-C6)-haloalkenyloxy-(C1-C6)-alkyl, ( (C2-C6)-haloalkenyl, (C2-C6)-cyanoalkenyl, (C2-C6)- Alkynyl, (C2-C6)-alkynyloxy-(C1-C6)-alkyl, (C2- C6)-haloalkynyloxy-(C1-C6)-alkyl, (C2-C6)-haloalkynyl alkynyl, (C2-C6)-cyanoalkynyl, (C3-C8)-cycloalkyl, (C3 -C8)-cycloalkyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl halo-(C3-C8)-cycloalkyl, halo-(C3-C8)-cycloalkyl, amino , (C1-C6)-alkylamino, di-(C1-C6)-alkyl-amino, (C3- C8)-cycloalkylamino, (C1-C6)-alkylcarbonylamino, (C1- C6)-Alkylthio-(C1-C6)-Alkyl, (C1-C6)-Haloalkylthio -(C1-C6)-Alkyl, (C1-C6)-Alkylsulfinyl-(C1-C6) -alkyl, (C1-C6)-haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-Alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-hal alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C 1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)-alkoxy- (C1-C6)-Alkylsulfinyl-(C1-C6)-alkyl, (C1-C6)- Alkoxy-(C1-C6)-alkylsulfonyl-(C1-C6)-alkyl, (C1 -C6)-Alkylcarbonyl-(C1-C6)-alkyl, (C1-C6)-haloal Alkylcarbonyl-(C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl- (C1-C6)-Alkyl, (C1-C6)-Haloalkoxycarbonyl-(C1-C6 )-alkyl, (C1-C6)-alkylsulfonylamino, aminosulfonyl-(C1 -C6)-alkyl, (C1-C6)-alkylaminosulfonyl-(C1-C6)-a alkyl or di-(C1-C6)-alkylaminosulfonyl-(C1-C6)-alkyl represents the rule, R a , R b , R c , R d are independently hydrogen, cyano, halogen, nitro, acetyl , hydroxy, amino, SCN, tri-(C1-C6)-alkylsilyl, (C3-C8 )-cycloalkyl, (C3-C8)-cycloalkyl-(C3-C8)-cycloalkyl (C1-C6)-alkyl-(C3-C8)-cycloalkyl, halo-(C3-C8 )-cycloalkyl, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C (1-C6)-cyanoalkyl, (C1-C6)-hydroxyalkyl, hydroxycarbo Nyl-(C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl-(C1- C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C2- (C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-cyanoalkenyl nyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C2-C6) -cyanoalkynyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-cyanoalkoxy, (C1-C6)-alkoxycarbonyl-(C1- C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C 1-C6)-Alkylhydroxyimino, (C1-C6)-alkoxyimino, (C1- C6)-Alkyl-(C1-C6)-alkoxyimino, (C1-C6)-haloalkyl -(C1-C6)-alkoxyimino, (C1-C6)-alkylthio, (C1-C6) -haloalkylthio, (C1-C6)-alkoxy-(C1-C6)-alkylthio, ( (C1-C6)-Alkylthio-(C1-C6)-alkyl, (C1-C6)-alkyls sulfinyl, (C1-C6)-haloalkylsulfinyl, (C1-C6)-alkoxy -(C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfinyl-( (C1-C6)-alkyl, (C1-C6)-alkylsulfonyl, (C1-C6)-halo Alkyl sulfonyl, (C1-C6)-alkoxy-(C1-C6)-alkyl sulfonyl (C1-C6)-alkylsulfonyl-(C1-C6)-alkyl, (C1-C6) -Alkylsulfonyloxy, (C1-C6)-alkylcarbonyl, (C1-C6)- Alkylthiocarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C6)- Alkylcarbonyloxy, (C1-C6)-alkoxycarbonyl, (C1-C6)- Haloalkoxycarbonyl, aminocarbonyl, (C1-C6)-alkylaminocarbonyl Nyl, (C1-C6)-alkylaminothiocarbonyl, di-(C1-C6)-alkyl Aminocarbonyl, di-(C1-C6)-alkylaminothiocarbonyl, (C2-C6 )-alkenylaminocarbonyl, di-(C2-C6)-alkenylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, (C1-C6)-alkylsulfonyl alkylamino, (C1-C6)-alkylamino, di-(C1-C6)-alkylamino, Aminosulfonyl, (C1-C6)-Alkylaminosulfonyl, Di-(C1-C6)-Aminosulfonyl alkylaminosulfonyl, (C1-C6)-alkylsulfoximino, aminothiocal (C1-C6)-alkylaminothiocarbonyl, di-(C1-C6)-alkyl -aminothiocarbonyl, (C3-C8)-cycloalkylamino, NHCO-(C1 -C6)-Alkyl ((C1-C6)-Alkylcarbonylamino), NHCO-O( C1-C6)-Alkyl ((C1-C6)-alkoxycarbonylamino) or NH CO-(C3-C8)-cycloalkyl ((C3-C8)-cycloalkylcarbonyl amino), where the group R a , R b , R c or R d at least one of represents a substituent other than hydrogen; Q is a heteroaromatic 9- or 12-membered fused bicyclic or or a tricyclic ring system, [ka]

[0009] TIFF2025032194000003.tif34152

[0010] R 4 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6) -cyanoalkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-alkoxy -(C1-C6)-alkyl, (C1-C6)-haloalkoxy-(C1-C6)-al Alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyloxy-(C1-C6 )-alkyl, (C2-C6)-haloalkenyloxy-(C1-C6)-alkyl, ( (C2-C6)-haloalkenyl, (C2-C6)-cyanoalkenyl, (C2-C6)- Alkynyl, (C2-C6)-alkynyloxy-(C1-C6)-alkyl, (C2- (C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloa Alkyl-(C3-C6)-cycloalkyl, (C1-C6)-alkyl-(C3-C6) -cycloalkyl, halo-(C3-C6)-cycloalkyl, (C1-C6)-alkyl Thio-(C1-C6)-alkyl, (C1-C6)-alkylsulfinyl-(C1-C 6)-alkyl, (C1-C6)-alkylsulfonyl-(C1-C6)-alkyl or represents (C1-C6)-alkylcarbonyl-(C1-C6)-alkyl, R 5 , R 6 are independently hydrogen, cyano, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloa alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C 6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6)-cycloalkyi alkyl, (C1-C6)-alkyl-(C3-C6)-cycloalkyl, (C1-C6)- Alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkoxyimino, ( (C1-C6)-Alkylthio, (C1-C6)-Haloalkylthio, (C1-C6)-A (C1-C6)-haloalkylsulfinyl, (C1-C6)-alkanylsulfinyl, (C1-C6)-haloalkylsulfonyl, (C1-C6)-alkylsulfonyl, (C1-C6)-alkylsulfonyloxy, (C1-C6)-alkylcarbonyl, (C1-C6)-haloal alkylcarbonyl, aminocarbonyl, (C1-C6)-alkylaminocarbonyl, di- (C1-C6)-Alkylaminocarbonyl, (C1-C6)-Alkylsulfonylamido (C1-C6)-alkylamino, di-(C1-C6)-alkylamino, aminos sulfonyl, (C1-C6)-alkylaminosulfonyl or di-(C1-C6)-alkenyl represents alkylaminosulfonyl, n represents 0, 1, or 2; Here, if Q represents Q2, then R c does not represent (C1-C6)-haloalkyl] It is a new compound.

[0011] Furthermore, the compounds of formula (I) may be used as pesticides, preferably as insecticides and / or insecticides. It has very good efficacy as a miticide and also has very good efficacy in general, especially with regard to crop plants. It has been found to have good plant compatibility. DETAILED DESCRIPTION OF THE INVENTION

[0012] The compounds according to the invention are defined in general terms by formula (I). Preferred substituents or ranges for the groups given in are exemplified below: Configuration 2-1 R 1 is preferably (C1-C4)-alkyl, (C1-C4)-hydroxyalkyl , (C1-C4)-haloalkyl, (C1-C4)-cyanoalkyl, (C1-C4)- Alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C 4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkenyloxy-( (C1-C4)-Alkyl, (C2-C4)-Haloalkenyloxy-(C1-C4)-a alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C2 -C4)-alkynyl, (C2-C4)-alkynyloxy-(C1-C4)-alkyl , (C2-C4)-haloalkynyloxy-(C1-C4)-alkyl, (C2-C4) -haloalkynyl, (C2-C4)-cyanoalkynyl, (C3-C6)-cycloalkynyl (C3-C6)-cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4 )-Alkyl-(C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl alkylamino, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C3- C6)-cycloalkylamino, (C1-C4)-alkylcarbonylamino, (C1- C4)-Alkylthio-(C1-C4)-alkyl, (C1-C4)-haloalkylthio -(C1-C4)-Alkyl, (C1-C4)-Alkylsulfinyl-(C1-C4) -alkyl, (C1-C4)-haloalkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-Alkylsulfonyl-(C1-C4)-alkyl, (C1-C4)-a alkylcarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkylcarbonyl represents aryl-(C1-C4)-alkyl or (C1-C4)-alkylsulfonylamino; , R a , R b , R c , R d are each independently preferably hydrogen, cyano, halogen, nitro Toro, acetyl, hydroxy, amino, SCN, tri-(C1-C4)-alkylsilyl , (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6) -cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, halo -(C3-C6)-cycloalkyl, (C1-C4)-alkyl, (C1-C4)-halo Alkyl, (C1-C4)-cyanoalkyl, (C1-C4)-hydroxyalkyl, ( (C1-C4)-alkoxy-(C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C2-C4) -alkynyl, (C2-C4)-haloalkynyl, (C2-C4)-cyanoalkynyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-sia Alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C 4)-Alkylhydroxyimino, (C1-C4)-alkoxyimino, (C1-C4) -Alkyl-(C1-C4)-alkoxyimino, (C1-C4)-haloalkyl-(C (1-C4)-alkoxyimino, (C1-C4)-alkylthio, (C1-C4)-halo Alkylthio, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C 4)-Alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C 4)-Alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl sulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkylsulfonyl Nyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyloxy, (C1 -C4)-Alkylcarbonyl, (C1-C4)-Haloalkylcarbonyl, Aminocarbonyl bonyl, aminothiocarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C 1-C4)-Alkyl-aminocarbonyl, (C1-C4)-Alkylsulfonylamino , (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, aminosulfonyl (C1-C4)-alkylaminosulfonyl, di-(C1-C4)-alkylaminosulfonyl Aminosulfonyl, aminothiocarbonyl, NHCO-(C1-C4)-alkyl ((C 1-C4)-Alkylcarbonylamino), NHCO-O(C1-C4)-Alkyl ( (C1-C4)-alkoxycarbonylamino) or NHCO-(C3-C6)-cyclo alkyl((C3-C6)-cycloalkylcarbonylamino), where the group R a , R b , R c or Rd at least one of represents a substituent other than hydrogen; Q is preferably a heteroaromatic 9-membered fused bicyclic ring selected from the group consisting of Q2, Q3, and Q16. represents a ring system of the formula [ka]

[0013] R 4 is preferably (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C 1-C4)-cyanoalkyl, (C1-C4)-hydroxyalkyl, (C1-C4)- Alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C 4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkenyloxy-( (C1-C4)-Alkyl, (C2-C4)-Haloalkenyloxy-(C1-C4)-a alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C2 -C4)-alkynyl, (C2-C4)-alkynyloxy-(C1-C4)-alkyl , (C2-C4)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6) -cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl-(C 3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C1-C4) -Alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl- (C1-C4)-Alkyl, (C1-C4)-Alkylsulfonyl-(C1-C4)- alkyl or (C1-C4)-alkylcarbonyl-(C1-C4)-alkyl, R 5 , R 6 are, independently of one another, preferably hydrogen, cyano, halogen, (C1-C4) -alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C 4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl , (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6) -cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, (C (1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy thioimino, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1 -C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1 -C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C 4)-Alkylsulfonyloxy, (C1-C4)-Alkylcarbonyl, (C1-C4 )-haloalkylcarbonyl, aminocarbonyl, (C1-C4)-alkylaminocarbonyl di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkyls sulfonylamino, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino aminosulfonyl, (C1-C4)-alkylaminosulfonyl or di-(C1- C4)-alkylaminosulfonyl; n preferably represents 0, 1 or 2, Here, if Q represents Q2, then R c does not represent (C1-C4)-haloalkyl.

[0014] Configuration 3-1 R 1 is particularly preferably (C1-C4)-alkyl, (C1-C4)-hydroxyalkyl alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)- Haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C 3-C6)-cycloalkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl or (C1- C4)-alkylsulfonyl-(C1-C4)-alkyl, R a , R b , R c , R d are, independently of one another, particularly preferably hydrogen, cyano, halogen , nitro, hydroxy, amino, SCN, tri-(C1-C4)-alkylsilyl, (C 3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6)-cyclo cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, halo-(C (3-C6)-cycloalkyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl (C1-C4)-cyanoalkyl, (C1-C4)-alkoxy-(C1-C4)- Alkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C 4)-cyanoalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl (C2-C4)-cyanoalkynyl, (C1-C4)-alkoxy, (C1-C4) -haloalkoxy, (C1-C4)-cyanoalkoxy, (C1-C4)-alkylhydroxide alkoxyimino, (C1-C4)-alkoxyimino, (C1-C4)-alkyl-(C1 -C4)-alkoxyimino, (C1-C4)-alkylthio, (C1-C4)-haloa alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkyls sulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl (C1-C4)-alkylsulfonyloxy, (C1-C4)-alkylcarbo Nyl, (C1-C4)-haloalkylcarbonyl, aminocarbonyl, (C1-C4)- Alkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C1- C4)-Alkylsulfonylamino, (C1-C4)-Alkylamino, Di-(C1-C 4)-Alkylamino, aminosulfonyl, (C1-C4)-alkylaminosulfonyl , di-(C1-C4)-alkylaminosulfonyl, NHCO-(C1-C4)-alkyl ((C1-C4)-alkylcarbonylamino), NHCO-O-(C1-C4)- Alkyl ((C1-C4)-alkoxycarbonylamino) or NHCO-(C3- C6)-cycloalkyl ((C3-C6)-cycloalkylcarbonylamino) , where the group R a , R b , R c or R d at least one of represents a substituent other than hydrogen; Q is particularly preferably a heteroaromatic 9-membered or 10-membered heteroaromatic group selected from the group consisting of Q2, Q3 and Q16. or a 12-membered fused bicyclic or tricyclic ring system, R 4 is particularly preferably (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-cyanoalkyl, (C1-C4)-hydroxyalkyl, (C1-C4 )-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1 -C4)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkenyloxy -(C1-C4)-Alkyl, (C2-C4)-Haloalkenyloxy-(C1-C4) -alkyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, ( (C2-C4)-alkynyl, (C2-C4)-alkynyloxy-(C1-C4)-al alkyl, (C2-C4)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C 6)-Cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl- (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C1-C 4)-Alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfini (C1-C4)-alkylsulfonyl-(C1-C4) -alkyl or (C1-C4)-alkylcarbonyl-(C1-C4)-alkyl death, R 5 , R 6 are, independently of one another, particularly preferably hydrogen, cyano, halogen, (C-C 4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2 -C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl Nyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C 6)-cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxyl Koximino, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, ( C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, ( (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1 -C4)-alkylsulfonyloxy, (C1-C4)-alkylcarbonyl, (C1- C4)-haloalkylcarbonyl, aminocarbonyl, (C1-C4)-alkylamino carbonyl, di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkylaminocarbonyl sulfonylamino, (C1-C4)-alkylamino, di-(C1-C4)-alkyl Amino, aminosulfonyl, (C1-C4)-alkylaminosulfonyl or di-(C 1-C4)-alkylaminosulfonyl, n particularly preferably represents 0, 1 or 2, Here, if Q represents Q2, then R c does not represent (C1-C4)-haloalkyl.

[0015] Configuration 4-1 R 1 is very particularly preferably (C1-C4)-alkyl, (C1-C4)-haloal alkyl or (C3-C6)-cycloalkyl, R a , R b , R c , R d are, independently of one another, very particularly preferably hydrogen, cyano, halo Alkyl, (C1-C4)-alkoxy, (C1-C4)-halogen chloroalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl, (C 1-C4)-Alkylthio, (C1-C4)-Alkylsulfinyl, (C1-C4)- Alkyl sulfonyl, (C1-C4)-haloalkylthio, (C1-C4)-haloalkyl (C1-C4)-haloalkylsulfonyl, NHCO-(C1-C4) -Alkyl ((C1-C4)-alkylcarbonylamino), NHCO-O(C1-C 4)-Alkyl ((C1-C4)-alkoxycarbonylamino) or NHCO-( (C3-C6)-Cycloalkyl ((C3-C6)-Cycloalkylcarbonylamino) represents where the group R a , Rb , R c or R d at least one of represents a substituent other than hydrogen; Q is very particularly preferably a heteroaromatic group selected from the group consisting of Q2, Q3 and Q16. represents a 9- or 12-membered fused bicyclic or tricyclic ring system of R 4 is very particularly preferably (C1-C4)-alkyl or (C1-C4)-alkanol. represents koxy-(C1-C4)-alkyl, R 5 is very particularly preferably hydrogen, cyano, halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl Chloroalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl-(C3- C6)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy thio, (C1-C4)-alkoxyimino, (C1-C4)-alkylthio, (C1-C4 )-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-halo Alkyl sulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-halo alkylsulfonyl, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkyl alkylcarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4)-alkenyl alkylaminocarbonyl, (C1-C4)-alkylsulfonylamino, (C1-C4)- alkylaminosulfonyl or di-(C1-C4)-alkylaminosulfonyl , R 6 very particularly preferably represents hydrogen, n very particularly preferably represents 0, 1 or 2, Here, if Q represents Q2, then R cdoes not represent (C1-C6)-haloalkyl.

[0016] Configuration 5-1 R 1 Specifically, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoro Fluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl represents tetrafluoroethyl or pentafluoroethyl; R a , R b , R c , R d are, independently of one another, specifically hydrogen, fluorine, chlorine, bromine, Iodine, cyano, methyl, ethyl, cyclopropyl, cyclobutyl, methoxy, ethyl sulfonyl, difluoromethyl, trifluoromethyl, trifluoromethoxy, trifluoro trifluoromethylthio, trifluoroethylthio, trifluoroethylsulfinyl, trifluoro ethylsulfonyl, difluoroethoxy, trifluoroethoxy, methyl(carbonyl) )amino, ethyl(carbonyl)amino, cyclopropyl(carbonyl)amino or methyl represents methoxy(carbonyl)amino, where the group R a , R b , R c or R d represents a substituent other than hydrogen, Q is specifically a heteroaromatic 9-membered or represents a 12-membered fused bicyclic ring system, R 4 Specifically, methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl It represents chill, R 5 Specifically, fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, Fluoromethyl, Fluoroethyl (CH2CFH2, CHFCH3), Difluoroethyl (CF2CH3, CH2CHF2, CHFCFH2), trifluoroethyl (CH2 CF3, CHFCHF2, CF2CFH2), tetrafluoroethyl (CHFCF3, CF2CHF2), pentafluoroethyl, trifluoromethoxy, difluorochloromethane Toxic, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl represents phenyl or trifluoromethylsulfonyl; R 6 specifically represents hydrogen, n specifically represents 0, 1 or 2; Here, if Q represents Q2, then R c is difluoromethyl or trifluoromethyl It does not represent a rule.

[0017] Configuration 5-2 R 1 Specifically, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoro Fluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl represents tetrafluoroethyl or pentafluoroethyl; R a , R b , R c , R d are, independently of one another, specifically hydrogen, fluorine, chlorine, bromine, Iodine, cyano, methyl, ethyl, cyclopropyl, cyclobutyl, methoxy, ethyl sulfonyl, difluoromethyl, trifluoromethyl, trifluoromethoxy, trifluoro trifluoromethylthio, trifluoroethylthio, trifluoroethylsulfinyl, trifluoro trifluoroethoxy, difluoropropoxy, methyl(carbonyl)amino, ethyl(carbonyl)amino, cyclopropyl(carbonyl)amino methoxy(carbonyl)amino or methoxy(carbonyl)amino; where the group R a , R b , R c or R d represents a substituent other than hydrogen, Q is specifically a heteroaromatic 9-membered or represents a 12-membered fused bicyclic ring system, R 4 Specifically, methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl It represents chill, R 5 Specifically, fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, Fluoromethyl, Fluoroethyl (CH2CFH2, CHFCH3), Difluoroethyl (CF2CH3, CH2CHF2, CHFCFH2), trifluoroethyl (CH2 CF3, CHFCHF2, CF2CFH2), tetrafluoroethyl (CHFCF3, CF2CHF2), pentafluoroethyl, trifluoromethoxy, difluorochloromethane Toxic, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl represents phenyl or trifluoromethylsulfonyl; R 6 specifically represents hydrogen, n specifically represents 0, 1 or 2; Here, if Q represents Q2, then R c is difluoromethyl or trifluoromethyl It does not represent a rule.

[0018] Configuration 6-1 R 1 stands in particular for ethyl, R a represents specifically hydrogen, R b stands in particular for hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine. , R c is especially hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, difluoromethyl , trifluoromethyl, methoxy, methyl(carbonyl)amino (-NH-CO-Me ), cyclopropyl(carbonyl)amino (-NH-CO-cyclopropyl), methoxy Di(carbonyl)amino (-NH-CO-OMe), ethylsulfonyl, 2,2-difluoro 2,2,2-trifluoroethoxy or 2,2,2-trifluoroethoxy 2,2,2-trifluoroethylsulfanyl (SCH2CF3) , R d represents in particular hydrogen, bromine, chlorine, cyano or trifluoromethyl, where the group R b , R c or R d represents a substituent other than hydrogen, Q is a heteroaromatic 9-membered fused bicyclic ring, in particular from the group consisting of Q2, Q3 and Q16. represents a ring system, [ka]

[0019] R 4 stands specifically for methyl, R 5 In particular, trifluoromethyl, pentafluoroethyl, trifluoromethoxy or represents trifluoromethylsulfonyl, R 6 represents specifically hydrogen, n particularly represents 2, Here, if Q represents Q2, then R cis difluoromethyl or trifluoromethyl It does not represent a rule.

[0020] Configuration 6-1a R 1 stands in particular for ethyl, R a represents specifically hydrogen, R b represents in particular hydrogen or trifluoromethyl, R c is especially hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, methoxy, methyl (carbonyl)amino (-NH-CO-Me), cyclopropyl(carbonyl)amino (-NH-CO-cyclopropyl), methoxy(carbonyl)amino (-NH-CO -OMe), ethylsulfonyl, 2,2-difluoroethoxy, 2,2,2-trifluoro represents 2,2,2-trifluoroethoxy or 2,2,2-trifluoroethylthio; R d represents in particular hydrogen, bromine, chlorine, cyano or trifluoromethyl, where the group R b , R c or R d represents a substituent other than hydrogen, Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the group Q2, R 4 stands specifically for methyl, R 5 In particular, trifluoromethyl, pentafluoroethyl, trifluoromethoxy or represents trifluoromethylsulfonyl, R 6 represents specifically hydrogen, n specifically represents 2.

[0021] Configuration 6-1b R 1 stands in particular for ethyl, R a represents specifically hydrogen, R brepresents specifically hydrogen, R c represents specifically hydrogen, R d stands in particular for bromine, cyano or trifluoromethyl, Q is a heteroaromatic 9-membered fused bicyclic ring system, especially from the group Q3, R 4 stands specifically for methyl, R 5 is in particular trifluoromethyl or pentafluoroethyl, R 6 represents specifically hydrogen, n specifically represents 2.

[0022] Configuration 6-1c R 1 stands in particular for ethyl, R a represents specifically hydrogen, R b stands in particular for hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine. , R c is in particular hydrogen, chlorine, bromine, cyano, methyl, difluoromethyl or trifluoromethyl. represents oromethyl, R d stands in particular for hydrogen, bromine or chlorine, where the group R b , R c or R d represents a substituent other than hydrogen, Q represents a heteroaromatic 9-membered fused bicyclic ring system, in particular from the group consisting of Q16; R 4 stands specifically for methyl, R 5 stands in particular for trifluoromethyl or pentafluoroethyl, R 6 represents specifically hydrogen, n specifically represents 2.

[0023] Configuration 6-2 R 1 stands in particular for ethyl, R a represents specifically hydrogen, R b stands in particular for hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine. , R c is especially hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, difluoromethyl , trifluoromethyl, methoxy, methyl(carbonyl)amino (-NH-CO-Me ), cyclopropyl(carbonyl)amino (-NH-CO-cyclopropyl), methoxy Di(carbonyl)amino (-NH-CO-OMe), ethylsulfonyl, 2,2-difluoro Fluoroethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy (-OCH2CF2CH3) or 2,2,2-trifluoroethylthio (2,2,2 -trifluoroethylsulfanyl: -SCH2CF3), R d represents in particular hydrogen, bromine, chlorine, cyano or trifluoromethyl, where the radical R b , R c or R d represents a substituent other than hydrogen, Q is a heteroaromatic 9-membered fused bicyclic ring, in particular from the group consisting of Q2, Q3 and Q16. represents a ring system, [ka]

[0024] R 4 stands specifically for methyl, R 5 In particular, trifluoromethyl, pentafluoroethyl, trifluoromethoxy or represents trifluoromethylsulfonyl, R 6 represents specifically hydrogen, n particularly represents 2, Here, if Q represents Q2, then R c is difluoromethyl or trifluoromethyl It does not represent a rule.

[0025] Configuration 6-2a R 1 stands in particular for ethyl, R a represents specifically hydrogen, R b represents in particular hydrogen or trifluoromethyl, R c is especially hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, methoxy, methyl (carbonyl)amino (-NH-CO-Me), cyclopropyl(carbonyl)amino (-NH-CO-cyclopropyl), methoxy(carbonyl)amino (-NH-CO -OMe), ethylsulfonyl, 2,2-difluoroethoxy, 2,2,2-trifluoro 2,2-difluoroethoxy, 2,2-difluoropropoxy (-OCH2CF2CH3) or 2,2 ,2-trifluoroethylthio, R d represents in particular hydrogen, bromine, chlorine, cyano or trifluoromethyl, where the group R b , R c or R d represents a substituent other than hydrogen, Q represents a heteroaromatic 9-membered fused bicyclic ring system, especially from the group Q2, R 4 stands specifically for methyl, R 5 In particular, trifluoromethyl, pentafluoroethyl, trifluoromethoxy or represents trifluoromethylsulfonyl, R 6 represents specifically hydrogen, n specifically represents 2.

[0026] Configuration 6-2b R 1stands in particular for ethyl, R a represents specifically hydrogen, R b represents specifically hydrogen, R c represents specifically hydrogen, R d stands in particular for bromine, cyano or trifluoromethyl, Q represents a heteroaromatic 9-membered fused bicyclic ring system, especially from the group Q3, R 4 stands specifically for methyl, R 5 is in particular trifluoromethyl or pentafluoroethyl, R 6 represents specifically hydrogen, n specifically represents 2.

[0027] Configuration 6-2c R 1 stands in particular for ethyl, R a represents specifically hydrogen, R b stands in particular for hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine. , R c is in particular hydrogen, chlorine, bromine, cyano, methyl, difluoromethyl or trifluoromethyl. represents methyl, R d stands in particular for hydrogen, bromine or chlorine, where the group R b , R c or R d represents a substituent other than hydrogen, Q represents a heteroaromatic 9-membered fused bicyclic ring system, in particular from the group consisting of Q16; R 4 stands specifically for methyl, R 5 stands in particular for trifluoromethyl or pentafluoroethyl, R 6 represents specifically hydrogen, n specifically represents 2.

[0028] In a preferred embodiment, the present invention provides a compound in which Q represents Q2 and R 1 , R 4 , R 5 , R 6 , R a , R b , R c , R d and n is the configuration (1-1) or the configuration (2-1) or the configuration (3- 1) or Configuration (4-1) or Configuration (5-1) or Configuration (5-2) or Configuration (6- 1) or the compounds of formula (I) having the definitions given in structure (6-2).

[0029] In a preferred embodiment, the present invention provides a compound in which Q represents Q3 and R 1 , R 4 , R 5 , R 6 , R a , R b , R c , R d and n is the configuration (1-1) or the configuration (2-1) or the configuration (3- 1) or Configuration (4-1) or Configuration (5-1) or Configuration (5-2) or Configuration (6- 1) or the compounds of formula (I) having the definitions given in structure (6-2).

[0030] In a preferred embodiment, the present invention provides a compound in which Q represents Q16 and R 1 , R 4 , R 5 , R 6 , R a , R b , R c , R d and n is the configuration (1-1) or the configuration (2-1) or the configuration (3 -1) or Configuration (4-1) or Configuration (5-1) or Configuration (5-2) or Configuration (6 -1) or the compounds of formula (I) having the definition given in structure (6-2).

[0031] In a preferred embodiment, the present invention provides a compound in which Q represents Q3 or Q16 and R 1 , R 4 , R 5 , R 6 , R a , R b , R c , R d and n is the structure (1-1) or the structure (2-1) or is configuration (3-1) or configuration (4-1) or configuration (5-1) or configuration (5-2) or relates to compounds of formula (I) having the definition given in structure (6-1) or structure (6-2). do.

[0032] In a preferred embodiment, the present invention provides a compound in which n represents 2 and Q, R 1 , R 4 , R 5 , R 6 , R a , R b , R c and R d Configuration (1-1) or Configuration (2-1) or Configuration (3-1 ) or Configuration (4-1) or Configuration (5-1) or Configuration (5-2) or Configuration (6-1 ) or compounds of formula (I) having the definition given in structure (6-2).

[0033] In the general or preferred definitions, unless otherwise specified, halogen includes fluorine, chlorine, selected from the group consisting of bromine and iodine, preferably fluorine, chlorine and bromine is selected from the group.

[0034] Aryl (including as part of a larger unit, e.g., arylalkyl) is another Unless otherwise defined, the aryl group is selected from the series phenyl, naphthyl, anthryl, and phenanthrenyl. is preferably phenyl.

[0035] In the context of the present invention, unless defined differently elsewhere, the term "alkyl" by itself or in combination with other terms, e.g., haloalkyl, 1 to 12 It refers to a group of saturated aliphatic hydrocarbon groups which have carbon atoms and may be branched or unbranched. It is understood to taste. C1-C 12 Examples of alkyl groups are methyl, ethyl, and n-propyl. , isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-butyl pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl ethylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, n-heptyl , n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Among these alkyl groups, C1-C6-alkyl groups are particularly preferred. It is a C1-C4-alkyl group.

[0036] According to the present invention, unless otherwise defined, the term "alkenyl" by itself or In combination with the term "linear or branched C2-C1 alkylene having at least one double bond" is understood to mean a 2-alkenyl group, for example vinyl, allyl, 1-propenyl, yl isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadiene 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl Among these, C2-C6-alkenyl groups are Preferred are C2-C4-alkenyl groups, particularly preferred.

[0037] According to the present invention, unless otherwise defined, the term "alkynyl" by itself or other In combination with the term, a linear or branched C2-C 12 - alkynyl groups, such as ethynyl, 1-propynyl and propargyl Among these, C3-C6-alkynyl groups are preferred, and C3-C4-alkynyl groups are preferred. Alkynyl groups are particularly preferred. Alkynyl groups may also contain at least one double bond. There is.

[0038] According to the present invention, unless otherwise defined, the term "cycloalkyl" by itself and in combination with further terms is understood to mean a C3-C8-cycloalkyl group, e.g. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Of these, C3-C6-cycloalkyl groups are preferred. .

[0039] The term "alkoxy" by itself or in combination with further terms, such as haloalkoxy, In combination, in the present invention, is understood to mean an O-alkyl group, where the term "alkyl" "Kill" is defined above.

[0040] Halogen-substituted groups, such as haloalkyl, are mono-halogenated or optionally substituted. In the case of polyhalogenation, the halogen atoms are identical and In this case, halogen is fluorine, chlorine, bromine or iodine. , in particular fluorine, chlorine or bromine.

[0041] Unless otherwise specified, optionally substituted groups may be mono- or polysubstituted. In the case of polysubstitution, the substituents may be the same or different.

[0042] The definitions or examples of groups given in general terms or listed within preferred ranges are The definitions of these groups apply correspondingly to the final product, as well as to the starting materials and intermediates. may be arbitrarily selected from each other, i.e., including combinations between each of the preferred ranges. They can be combined.

[0043] Preferred according to the present invention include combinations of the meanings listed above as preferred. The use of a compound of formula (I)

[0044] Particularly preferred according to the invention are combinations of the meanings listed above as particularly preferred. The use of a compound of formula (I) comprising

[0045] Very particularly preferred according to the invention are the definitions listed above as very particularly preferred. The use of compounds of formula (I) includes any combination thereof.

[0046] Most preferred according to the present invention are combinations of the meanings listed above as most preferred. The use of a compound of formula (I) comprising the combination

[0047] Of particular use according to the invention are the combinations of meanings listed above as being particularly emphasized. The compound of formula (I) includes a combination of:

[0048] Depending on the nature of the substituents, the compounds of formula (I) may be geometrically and / or optically active. These stereoisomers may be in the form of a mixture of corresponding isomers of different composition. The isomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present invention therefore provides pure stereoisomers and any desired mixtures of these isomers. It encompasses both.

[0049] The compounds of formula (I) according to the present invention can be obtained by the method shown in the following scheme: R: Process A The compound of formula (I) wherein Q represents Q1 to Q9, Q16 or Q19 can be prepared by known methods, for example, WO2009 / 131237, WO2010 / 125985, WO2011 / 04340 4, WO2011 / 040629, WO2012 / 086848, WO2013 / 018 928, WO2015 / 000715, WO2015 / 198859, WO2016 / 0 39444, WO2016 / 039441, WO2016 / 116338 and WO2 It can be prepared similarly to the method described in 015 / 121136. [ka]

[0050] base R 1 , R 4 , R 5 , R 6 , R a , R b , R c , R d and n has the above meaning, A 2 and A 3 represents CH or N, and A 4 is O, S or -NR 4 represents X 1 Ha Haroge Represents the

[0051] Step a) The compound of formula (IV) can be prepared by reacting a compound of formula (II) with a compound of formula (III) in the presence of a condensing agent or a base. ) with a carboxylic acid in analogy to the method described in US Pat. No. 5,576,335. It is possible.

[0052] Compounds of formula (II) are commercially available or can be prepared by known methods, e.g., US2 003 / 69257, WO2006 / 65703, WO2009 / 131237, WO2 010 / 125985, WO2011 / 043404, WO2011 / 040629, W O2012 / 086848, WO2013 / 018928 or WO2015 / 0007 It can be prepared by methods similar to those described in 15.

[0053] Carboxylic acids of formula (III) are commercially available or can be prepared by known methods. Possible preparation routes are described in Processes H and I.

[0054] The reaction of the compound of formula (II) with the carboxylic acid of formula (III) can be carried out neat or The reaction can be carried out in a solvent, which is selected from conventional solvents which are inert under the general reaction conditions. It is preferred to carry out the reaction in a solvent containing ethers such as diisopropyl ether, ... hexane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons, e.g. Dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzyl nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons, such as aprotic polar solvents, such as toluene or xylene; aprotic polar solvents, such as N,N-dimethylformamide Preference is given to N-methylpyrrolidone or N-methylpyrrolidone, or nitrogen compounds such as pyridine.

[0055] Suitable condensing agents include, for example, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide Carbodiimide such as EDCI hydrochloride or 1,3-dicyclohexylcarbodiimide It is an imide.

[0056] Suitable bases are the inorganic bases typically used in such reactions. or alkaline earth metal acetates, phosphates, carbonates and bicarbonates, for example. It is preferred to use a base selected from the following: Particularly preferred here is sodium acetate , sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, Sodium bicarbonate and potassium bicarbonate.

[0057] The reaction can be carried out under reduced pressure, normal pressure, or elevated pressure, and at temperatures between 0°C and 180°C. Preferably, the reaction is carried out at atmospheric pressure and at a temperature of 20 to 140°C.

[0058] Step b) The compound of formula (V) can be prepared, for example, from the compounds described in WO2009 / 131237 and WO2010 / 12598 5, WO2011 / 043404, WO2011 / 040629, WO2012 / 086 848, WO2013 / 018928, WO2015 / 000715 and WO2015 by condensing the compound of formula (IV) in the same manner as described in JP 121136. It can be prepared by the following method.

[0059] The conversion to compounds of formula (V) can be carried out neat or in a solvent and is generally under the following reaction conditions: It is preferred to carry out the reaction in a solvent selected from conventional solvents which are inert under the conditions. ethers, such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-diisopropyl ether, methoxyethane, tert-butyl methyl ether; halogenated hydrocarbons, for example, dichloromethane, Chloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons, such as , toluene or xylene; aprotic polar solvents, such as N,N-dimethylformamide Imidazole or N-methylpyrrolidone, or nitrogen compounds such as pyridine, are preferred.

[0060] The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.

[0061] An example of a suitable condensing agent is 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. Carbodiimides such as EDCI hydrochloride or 1,3-dicyclohexylcarbodiimide Imides; anhydrides such as acetic anhydride and trifluoroacetic anhydride; triphenylphosphine, A mixture of a base and carbon tetrachloride, or triphenylphosphine and an azodiester, e.g. For example, a mixture of diethyl azodicarboxylate.

[0062] Examples of suitable acids that can be used in the described reactions are sulfonic acids such as paratoluenesulfonic acid. carboxylic acids such as sulfonic acid; acetic acid, or polyphosphoric acid.

[0063] Examples of suitable bases are pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo Nitrogen heterocycles such as [5.4.0]-7-undecene (DBU); triethylamine and Tertiary amines such as N,N-diisopropylethylamine; potassium phosphate, potassium carbonate and inorganic bases such as sodium hydroxide and sodium hydride.

[0064] An example of a suitable chlorinating agent is phosphorus oxychloride.

[0065] The reaction can be carried out under reduced pressure, atmospheric pressure, or elevated pressure, and at temperatures between 0°C and 200°C. can be done.

[0066] Step c) A compound of formula (I) wherein n represents 0 can be prepared by reacting a compound of formula (V) with a compound of formula (VIa) in the presence of a base or by reacting with a compound of formula (VIb) It can be prepared by the following method.

[0067] Methyl mercaptan derivatives of formula (VIa), such as methyl mercaptan, ethyl mercaptan The butane or isopropyl mercaptan is commercially available or can be prepared by known methods. Laws such as US2006 / 25633, US2006 / 111591, and US28200 62, Chemical Communications, 13(2000), 1163 -1164 or Journal of the American Chemical Prepared in the same manner as described in Society, 44 (1922), p. 1329. It is possible.

[0068] The conversion to compounds of formula (I) in which n represents 0 can be carried out neat or in a solvent, preferably Preferably, the reaction is carried out in a solvent selected from conventional solvents which are inert under the general reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1 ,2-dimethoxyethane, tert-butyl methyl ether; nitriles, such as acetonitrile tolyl or propionitrile; aromatic hydrocarbons, such as toluene or xylene; non-propionitrile Protic polar solvents, such as N,N-dimethylformamide, N-methylpyrrolidone, or Dimethyl sulfoxide is preferred.

[0069] Examples of suitable bases are alkali metal or alkaline earth metal acetates, phosphates and charcoal. Inorganic bases from the group consisting of cesium carbonate, sodium carbonate and Potassium carbonate is preferred. Further suitable bases are alkali metal hydrides, such as sodium hydride. It is thorium.

[0070] Alternatively, salts of mercaptan derivatives (compounds of formula (VIb)), such as sodium ethoxylates, Sodium ethanethiolate, sodium methanethiolate or sodium isopropanethiolate can be used directly without the addition of further base. The reaction is carried out under reduced pressure and atmospheric pressure. The reaction can be carried out under elevated pressure or at temperatures between 0°C and 200°C.

[0071] In the reaction described, X 1 preferably represents a fluorine atom or a chlorine atom.

[0072] R a , R b , R c or R d Similarly, when represents a halogen (e.g., chlorine or fluorine), In this case, for example, methyl mercaptan, ethyl mercaptan or isopropyl mercaptan Use X 1 single substitution with alkyl mercaptans as well as multiple substitutions with alkyl mercaptans is possible.

[0073] Step d) Compounds of formula (I) where n represents 1 can be prepared by oxidizing compounds of formula (I) where n represents 0. The oxidation is generally carried out in a conventional solvent that is inert under the general reaction conditions. The reaction is carried out in a solvent selected from halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohol, For example, methanol or ethanol; formic acid, acetic acid, propionic acid or water are preferred.

[0074] Examples of suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate. It is.

[0075] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0076] Step e) Compounds of formula (I) where n is 2 can be prepared by oxidizing compounds of formula (I) where n is 1. The oxidation is generally carried out in a solvent. For example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chloroform. Benzene; alcohols, such as methanol or ethanol; formic acid, acetic acid, propionic acid Alternatively, water is preferred.

[0077] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0078] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0079] Step f) Compounds of formula (I) where n is 2 can also be obtained by oxidizing compounds of formula (I) where n is 0. It can also be prepared in a one-pot process by The oxidation is generally carried out in a solvent, such as a halogenated hydrocarbon, e.g., dichloromethane, chloroform, or the like. chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols, e.g. For example, methanol or ethanol; formic acid, acetic acid, propionic acid or water are preferred.

[0080] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0081] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0082] R a , R b , R c or R d Similarly, represents alkylsulfanyl (= alkylthio). In this case, a suitable oxidizing agent, such as hydrogen peroxide and meta-chloroperbenzoic acid, may be used to convert the methyl R using methyl mercaptan, ethyl mercaptan or isopropyl mercaptan 1 Oxidation of sulfur atoms to sulfones and alkylsulfanyl substitution of alkylsulfanyl groups Oxidation to sulfonyl can be carried out.

[0083] Process B [ka]

[0084] base R 1 , R a , R b , R c , R d and n has the above meaning, and X 1 represents a halogen , R 8 represents C1-C4-alkyl.

[0085] Step a) Compounds of formula (VIII) can be prepared from compounds of formula (VII) via halogenation in a known manner. This can be done, for example, by directed ortho-lithiation followed by the appropriate This can be achieved through carbanion capture with an appropriate electrophilic halogenating agent, or is Bioorganic & Medicinal Chemistry Letter s, 24(2014), 4236-4238; Tetrahedron, 58(2002 ), 6723-6728 and WO2003 / 010146 This can be achieved via a similar electrophilic aromatic halogenation. Compounds of formula (VII) can be prepared It is either commercially available or can be synthesized via esterification from a compound of formula (XXV). It is possible.

[0086] Step b) The compound of formula (III) can be prepared by the method described in Synthesis 1987, 6, 586-587, Te trahedron Letters 2006,47,565-567 or Chem In a manner similar to that described in MedChem 2010, 5, 65-78, a compound of formula (VI It can be synthesized from compound II) via hydrolysis.

[0087] Examples of suitable bases are, for example, lithium hydroxide or sodium hydroxide. The solvent may be polar aprotic and protic solvents and mixtures thereof, such as ethanol. The solvent may be toluene, tetrahydrofuran or water.

[0088] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0089] Step c) The compound of formula (IX) in which n represents 0 can be prepared by reacting a compound of formula (VIII) with a compound of formula (V) in the presence of a base. Ia) or by reacting with a compound of formula (VIb) It can be prepared by:

[0090] Mercaptan derivatives of formula (VIa), such as methyl mercaptan, ethyl mercaptan Alternatively, isopropyl mercaptan may be commercially available or may be prepared by known methods, e.g. For example, US2006 / 25633, US2006 / 111591, US2820062, C chemical communications,13(2000),1163-116 4 or Journal of the American Chemical Society It can be prepared in a similar manner to that described in Society, 44 (1922), p. 1329. This can be done.

[0091] The conversion to compounds of formula (IX) where n represents 0 can be carried out neat or in a solvent. The reaction is carried out in a solvent selected from conventional solvents which are inert under the general reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, nitriles, e.g., 1,2-dimethoxyethane, tert-butyl methyl ether; acetonitrile or propionitrile; aromatic hydrocarbons, such as toluene or xylene aprotic polar solvents, such as N,N-dimethylformamide, N-methylpyrrolidone Alternatively, dimethyl sulfoxide is preferred.

[0092] Examples of suitable bases are alkali metal or alkaline earth metal acetates, phosphates and charcoal. Inorganic bases from the group consisting of cesium carbonate, sodium carbonate and Potassium carbonate is preferred. Further suitable bases are alkali metal hydrides, such as sodium hydride. It is thorium.

[0093] Alternatively, salts of mercaptan derivatives (compounds of formula (VIb)), such as sodium ethoxylates, Sodium ethanethiolate, sodium methanethiolate or sodium isopropanethiolate can be used directly without the addition of further base. The reaction is carried out under reduced pressure and atmospheric pressure. The reaction can be carried out under elevated pressure or at temperatures between 0°C and 200°C.

[0094] In the reaction described, X 1 preferably represents a fluorine atom or a chlorine atom.

[0095] R a , R b , R c or R d Similarly, when represents a halogen (e.g., chlorine or fluorine), In this case, for example, methyl mercaptan, ethyl mercaptan or isopropyl mercaptan is used. Use X 1 single substitution with alkyl mercaptans as well as multiple substitutions with alkyl mercaptans It is possible.

[0096] Process C Compounds of formula (I) in which Q represents Q1 to Q9, Q16 or Q19 can be prepared by known methods, for example by W O2009 / 131237, WO2010 / 125985, WO2011 / 043404 , WO2011 / 040629, WO2012 / 086848, WO2013 / 0189 28, WO2015 / 000715, WO2015 / 198859, WO2016 / 03 9444, WO2016 / 039441, WO2016 / 116338 and WO201 It can be prepared similarly to the method described in US Pat. No. 5 / 121136. [ka]

[0097] base R 1 , R 4 , R 5 , R 6 , R a , R b , R c , R d and n has the above meaning, A 2 and A 3 represents CH or N, and X 1 represents a halogen, and A 4 is O, S or -NR 4 represents R 8 represents (C1-C4)-alkyl.

[0098] Steps a) and b) Compounds of formula (IXa) in which n represents 2 can be prepared by oxidizing compounds of formula (IX) in which n represents 0. The oxidation is generally carried out in a solvent. dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or Chlorobenzene; alcohols, such as methanol or ethanol; formic acid, acetic acid, propyl Acid or water is preferred.

[0099] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0100] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0101] Compounds of formula (IXb) in which n represents 1 can be prepared by oxidizing compounds of formula (IX) in which n represents 0. It can be prepared similarly by

[0102] A compound of formula (IXa) in which n is 2 oxidizes a compound of formula (IXb) in which n is 1 It can be prepared similarly by

[0103] Step c) Compounds of formula (X), where n is 0, 1 or 2, can be converted to compounds of formula (IX, n=0) in the presence of a base Prepared by hydrolysis of compound (IXa, n=2) or (IXb, n=1) The hydrolysis is generally carried out in a solvent, such as an alcohol, e.g., methanol or ethanol. ethanol; water; ethers, such as diisopropyl ether, dioxane, tetrahydrofuran oran, 1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, e.g. Acetonitrile or propionitrile; aromatic hydrocarbons, such as toluene or xylene aprotic polar solvents, such as N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide; or mixtures of the above solvents are preferred.

[0104] Examples of suitable bases are alkali metal or alkaline earth metal acetates, phosphates and charcoal. Inorganic bases from the group consisting of cesium carbonate, sodium carbonate and Potassium carbonate is preferred.

[0105] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 200°C. It is possible.

[0106] Further conversion of compounds of formula (X) to compounds of formula (I) is carried out analogously to Process A. can be.

[0107] Step d) The compound of formula (XI) can be prepared by reacting a compound of formula (II) with a compound of formula (X) in the presence of a condensing agent or a base. It can be prepared by reaction with a carboxylic acid.

[0108] Compounds of formula (II) are commercially available or can be prepared by known methods, e.g., US2 003 / 069257, US2012 / 0319050, WO2011 / 107998 Alternatively, it can be prepared analogously to the method described in WO2010 / 91310.

[0109] A compound of formula (II) with a carboxylic acid of formula (X) (wherein n is 0, 1 or 2) The reaction can be carried out neat or in a solvent, preferably one that is inert under the prevailing reaction conditions. The reaction is carried out in a solvent selected from conventional solvents which are hydrophobic. ethers, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated Hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane or chlorobenzene; nitriles, such as acetonitrile or propionitrile; aromatic aromatic hydrocarbons, such as toluene or xylene; aprotic polar solvents, such as N,N-dichloromethane; Methylformamide or N-methylpyrrolidone, or nitrogen compounds such as pyridine preferable.

[0110] Suitable condensing agents include, for example, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide Carbodiimides such as EDCI hydrochloride and 1,3-dicyclohexylcarbodiimide chlorine, thionyl chloride or oxalyl chloride.

[0111] Suitable bases are the inorganic bases typically used in such reactions. or alkaline earth metal acetates, phosphates, carbonates and bicarbonates, for example. It is preferred to use a base selected from the following: Particularly preferred here is sodium acetate , sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, Sodium bicarbonate, potassium bicarbonate. Further preferred bases are alkali metal hydrides. , for example sodium hydride.

[0112] The reaction can be carried out under reduced pressure, normal pressure, or elevated pressure, and at temperatures between 0°C and 180°C. Preferably, the reaction is carried out at atmospheric pressure and at a temperature of 20 to 140°C.

[0113] Step e) The compound of formula (I) wherein n is 0, 1 or 2 can be prepared by reacting a compound of formula (XI) in the presence of a base It can be prepared by condensation.

[0114] The conversion to compounds of formula (I) where n is 0, 1 or 2 can be carried out neat or in a solvent. and preferably in a solvent selected from conventional solvents which are inert under the prevailing reaction conditions. The reaction is carried out in a solvent such as ether, diisopropyl ether, dioxane, tetrahydrofuran, etc. Dorofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated Hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane benzene or chlorobenzene; nitriles, for example, acetonitrile or propionitrile; Aromatic hydrocarbons, such as toluene or xylene; aprotic polar solvents, such as N , N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, such as Pyridine is preferred.

[0115] Suitable bases are the inorganic bases typically used in such reactions. or alkaline earth metal acetates, phosphates, carbonates and bicarbonates, for example. It is preferred to use a base selected from the following: Particularly preferred here is sodium acetate , sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, Sodium bicarbonate and potassium bicarbonate.

[0116] The reaction can be carried out under reduced pressure, atmospheric pressure, or elevated pressure, and at temperatures between 0°C and 200°C. can be done.

[0117] Process D Compounds of formula (I) in which Q represents Q10, Q11, Q14 and Q15 can be prepared by known methods. For example, US2009 / 203705, US2012 / 258951, WO2013 / 3298, WO2016 / 071214 or J.Med Chem.31, (198 8) It can be prepared similarly to the method described in 1590-1595. [ka]

[0118] base R 1 , R 5 , R 6 , R a , R b , R c , R d and n have the above meanings. 2 , A 3 and A 5 represents CH or N, and A 4 is CR 5 or N (where A 2 , A 3 , A 4 and A5 (both do not represent N), X 1 represents a halogen.

[0119] Step a) The carboxylic acid of formula (III) is reacted with O,N-dimethylhydroxylamine hydrochloride in the presence of Similar to the methods described in WO2011 / 75643 or EP2671582, to Weinreb amides of formula (XII).

[0120] Carboxylic acids of formula (III) are commercially available or can be prepared by known methods. Possible preparation routes are described in Processes H, I and J.

[0121] Steps b and c) The compound of formula (XII) can then be reacted with the compound of formula (XII) by known methods, for example, the method described in WO2011 / 75643 Similar to the method described in Thus, the compound of formula (XIV) can be converted into a ketone of formula (XIII). Subsequent halo- It can be obtained by genification.

[0122] Step d) Compounds of formula (XVI) can be prepared by cyclizing compounds of formula (XIV) with amines of formula (XV). The cyclization can be carried out by, for example, the methods described in WO2005 / 66177, WO201 2 / 88411, WO2013 / 3298, US2009 / 203705, US2012 / 258951, WO2012 / 168733, WO2014 / 187762 or J. Similar to the method described in Med. Chem. 31 (1988) 1590-1595 and by known methods, for example, in ethanol, acetonitrile or N,N-dimethylformamide. The reaction is carried out in methylformamide.

[0123] Compounds of formula (XV) are commercially available.

[0124] Step e) The compound of formula (I) in which n represents 0 can be prepared by reacting a compound of formula (XVI) with a compound of formula (VIa The mercaptan of formula (VIa) can be prepared by reacting the compound of formula (VIa) with a compound of formula (VIa) derivatives such as methyl mercaptan, ethyl mercaptan or isopropyl mercaptan Tan is commercially available or can be prepared by known methods, e.g., US2006 / 2563 3, US2006 / 111591, US2820062, Chemical Commu nications,13(2000),1163-1164 or Journal o f the American Chemical Society,44(1922) It can be prepared similarly to the method described in J. Am. Chem. Soc., p. 1329.

[0125] Alternatively, salts of mercaptan derivatives (VIb), such as sodium ethanethiolate, Sodium methanethiolate or sodium isopropanethiolate with additional base It can be used directly without the addition of

[0126] Steps f and g) Compounds of formula (I) where n represents 1 can be prepared by oxidizing compounds of formula (I) where n represents 0. The oxidation can be carried out using a suitable oxidizing agent, such as hydrogen peroxide, meta-chloroperoxide, or the like. This is carried out by known methods using benzoic acid or sodium periodate.

[0127] Compounds of formula (I) where n represents 2 can be prepared by oxidizing compounds of formula (I) where n represents 1. It can be prepared by the following method.

[0128] The oxidation is generally carried out in a solvent such as a halogenated hydrocarbon, e.g., dichloromethane, chloroform, or the like. chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols, e.g. For example, methanol or ethanol; formic acid, acetic acid, propionic acid or water are preferred. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0129] Step h) Compounds of formula (I) in which n represents 2 can also be obtained by oxidizing compounds of formula (I) in which n represents 0. It can also be prepared in a one-step process by: The oxidation is generally carried out in a solvent. Halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloromethane, chloroethane or chlorobenzene; alcohols, such as methanol or ethanol; Acid, acetic acid, propionic acid or water are preferred. Examples of suitable oxidizing agents are hydrogen peroxide and methyl peroxide. It is terchloroperbenzoic acid.

[0130] Process E Compounds of formula (I) in which Q represents Q16 can be prepared by known methods, for example, by methods described in WO2014 / 14229 It can be prepared similarly to the method described in 2. [ka]

[0131] base R a , R b , R c , R d , R 4 , R 5and R 6 has the meaning given above .X 1 represents a halogen.

[0132] Step a) The compound of formula (XVII) can be prepared by reacting the compound of formula (III) with an ammonia source in the presence of a condensing agent. By reacting, US5374646 or Bioorganic and M edicinal Chemistry Letters 2003,13,1093- It can be prepared similarly to the method described in 1096.

[0133] Carboxylic acids of formula (III) are commercially available or can be prepared by known methods. Possible preparation routes are described in Processes H and I.

[0134] The reaction of the compound of formula (III) with an ammonia source is inert under the prevailing reaction conditions. It is preferably carried out in a solvent chosen from the usual solvents: ethers, for example dioxane or or tetrahydrofuran is preferred.

[0135] A suitable condensing agent is, for example, carbonyldiimidazole.

[0136] The reaction can be carried out under reduced pressure, atmospheric pressure or elevated pressure. Preferably, the reaction is carried out under atmospheric pressure. The reaction is carried out at high pressure and at a temperature of 20-70°C.

[0137] Step b) Formula (V 1-A ) can be prepared by the reaction of a compound of formula (XVII) in a basic medium in the presence of a palladium catalyst with a compound of formula (XIX), can be prepared in a similar manner to that described in

[0138] The compound of formula (XIX) can be prepared by the method described in, for example, WO2014 / 142292. The palladium catalyst used can be prepared in a similar manner. bis-(diphenylphosphino)ferrocene]dichloropalladium(II) Often the base used is an inorganic base such as potassium tert-butoxide. .

[0139] The reaction is carried out in a solvent, often toluene.

[0140] The reaction can be carried out under reduced pressure, atmospheric pressure or elevated pressure. It is carried out at atmospheric pressure and at temperatures between 20 and 110°C.

[0141] Formula (V 1-A The further conversion of compounds of formula (I) to compounds of formula (I) is analogous to process A. This is carried out.

[0142] Process F The compound of formula (I) in which n represents 2 and Q represents Q1 to Q9, Q16 or Q19 is a known compound. Methods, e.g., WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO20 13 / 018928, WO2015 / 000715 and WO2015 / 121136 It can be prepared analogously to the method described. [ka]

[0143] base R 1 , R a , R b , Rc , R d , R 4 , R 5 , R 6 , A 2 and A 3 has the above meaning. Has A 4 is O, S or NR 4 represents X 1 is a halogen, preferably bromine or iodine Represents an element.

[0144] Step a) Alternatively, compounds of formula (I) in which n represents 2 may also be used as compounds of formula (I), as described, for example, in the Journal of Organic Chemistry 2005, 70, 2696-2700 The halogenation of a compound of formula (VIc) proceeds from a compound of formula (V) in a manner similar to that described in They can also be prepared in a one-step process by sulfonation. The reaction is carried out in a polar aprotic solvent, such as dimethyl sulfoxide and N,N-dichloromethane. It is preferred to use methylformamide.

[0145] Compounds of formula (VIc) are commercially available or can be prepared by known methods, e.g. anic Synthesis 1977,57,88-92;Tetrahedron Letters 1979,9,821-824 and Bulletin de la Societe Chimique de France 1958,4,447-4 It can be prepared similarly to the method described in 50.

[0146] Examples of suitable sulfur reagents are lithium, sodium or potassium salts of sulfinic acids. .

[0147] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0148] Process G Compounds of formula (I) in which Q represents Q12, Q13, Q17, Q18 or Q20 can be prepared according to the known Methods, e.g., those described in WO2010 / 091310, WO2012 / 66061 or WO20 It can be prepared analogously to the method described in J.P. 13 / 099041. [ka]

[0149] base R a , R b , R c , R d , R 5 and R 6 has the meaning given above. 2 , A 3 oh Yobi A 6 represents CH or N, and X 1 and X 2 represents a halogen.

[0150] Step a) The compound of formula (XXII) can be prepared, for example, by the method described in WO2010 / 091310 and WO 2012 / 6 6061, WO2013 / 099041 or Tetrahedron 1993,49 , 10997-11008, under basic conditions, a compound of formula (XX) can be prepared by reacting a compound of formula (XXI) with a compound of formula (XXI).

[0151] Compounds of formula (XX) are commercially available or can be prepared by known methods, e.g., WO2 005 / 100353, WO2012 / 66061, or European Jour nal of Medicinal Chemistry 2010,45,2214- It can be prepared similarly to the method described in 2222.

[0152] Compounds of formula (XXI) are commercially available or can be prepared by known methods, e.g., WO 2013 / 43518, EP2168965 or Journal of Medici Those listed in nal Chemistry 2003,46,1449-1455 It can be prepared in a similar manner to the method described above.

[0153] The base used is usually a base such as sodium hydride, potassium carbonate or cesium carbonate. It is an inorganic base.

[0154] The conversion to a compound of formula (XXII) is usually carried out in a solvent, preferably a nitrile, e.g. in acetonitrile or propionitrile, or in aprotic polar solvents such as N , N-dimethylformamide or N-methylpyrrolidone.

[0155] The reaction can be carried out under reduced pressure, atmospheric pressure, or elevated pressure, and at temperatures between 0°C and 200°C. can be done.

[0156] Alternatively, a compound of formula (XX) is reacted with a compound of formula (XXI) to give a compound of formula (XXII). Reactions with substances are, for example, Angewandte Chemie Int.Ed.2011, 50, 8944-8947, a palladium-catalyzed N-arylation reaction was performed. This can also be achieved by encapsulation.

[0157] Further conversion of compounds of formula (XXII) to compounds of formula (I) is analogous to process A. This is carried out.

[0158] Process H [ka]

[0159] Carboxylic acids of formula (III) are commercially available or can be prepared by known methods, e.g. Tetrahedron,40(1984),311-314, Monatshefte fuer Chemie,139(2008),673-684,Synlett,3 (2006),379-382;Indian Journal of Chemist ry,Section B:Organic Chemistry Including Medicinal Chemistry,22B(1983),178-179;J Ournal of Organic Chemistry,55(1990),283 8-2842;Heterocycles,60(2003),953-957;Che mical Communications,2(2002),180-181,WO2 015 / 071178, Bioorganic & Medicinal Chemistry try Letters,24(2014),4236-4238;Tetrahedr on, 58(2002), 6723-6728 and WO2003 / 010146 It can be prepared from benzylamine or hetarylmethanamine in a similar manner to do. [ka]

[0160] base R a , R b , R c and R dhas the above-mentioned meaning, E represents hydrogen or halogen, X 1 represents a halogen. 2 is methyl, C(O)OR 8 , or cyano. 8 teeth , hydrogen or C1-C6-alkyl.

[0161] Step a) The compound of formula (XXIV) is described in Tetrahedron, 40 (1984), 311-3 14 or Monatshefte fuer Chemie,139(2008),6 Benzylamine of formula (XXIII) or The reaction of hetarylmethanamines with the corresponding carbonyl compounds under acidic or basic conditions It can be synthesized by condensation of

[0162] Compounds of formula (XXIII) are commercially available or can be prepared by known methods, e.g. WO1997 / 41846;US2011 / 0105753;Journal of M edicinal Chemistry,46(2003),461-473;WO20 10 / 024430;WO2005 / 111003;Journal of Heter The method described in Cyclic Chemistry, 23 (1986), 989-990 It can be prepared similarly to

[0163] Step b) Compounds of formula (XXV) can be prepared by known methods, for example under acidic, basic or thermal conditions. Formula (XXIV)(Y 2 =C(O)OR 8 or cyano) by hydrolysis of the compound It can be prepared by the following method.

[0164] The compound of formula (XXV) can be prepared by the method described in Synlett, 3 (2006), 379-382; ian Journal of Chemistry,Section B:Organ ic Chemistry Including Medicinal Chemist ry,22B(1983),178-179;Journal of Organic Chemistry,55(1990),2838-2842;Heterocycle s,60(2003),953-957;Chemical Communicatio ns, 2(2002), 180-181 and the method described in WO2015 / 071178 Analogously to the formula (XXIV) (Y 2 via benzylic oxidation from the compound (if methyl) can be adjusted.

[0165] Step c) Compounds of formula (III-A) can be prepared from compounds of formula (XXV) via halogenation in a known manner. This can be prepared by, for example, directed ortho-lithiation followed by via carbanion capture with an appropriate electrophilic halogenating reagent or via Organic & Medicinal Chemistry Letters,24 (2014),4236-4238;Tetrahedron,58(2002),67 Similar to the methods described in WO2003 / 010146 and WO23-6728, This can be accomplished via carboxylic acid derivative-directed halogenation.

[0166] Process I R 1 , R a , R b , Rc , R d , R 5 , R 6 , A 2 , A 3 and A 4 has the above meaning and R 9 represents (C1-C4)-alkyl, and Tf represents triflate (CF3SO2-). wherein Ts represents tosylate (CH3C6H4SO2-), It can be prepared by known methods, for example by the process described below. [ka]

[0167] Step a) Compounds of formula (XXVII) are commercially available or can be purchased from Bioorganic & Medicinal Chemistry Letters 2016,26,2 526-2530 or Tetrahedron Letters 2012,53,3 654-3657, the compound of formula (XXVI) can be converted into a free radical It can be prepared via bromination.

[0168] The brominating agent used may be, for example, N-bromosuccinimide. azo compounds such as nitriles (AIBN) or peracids such as dibenzoyl peroxide The chlorine compounds can be used as radical initiators.

[0169] The solvent used is preferably an aprotic solvent, such as carbon tetrachloride.

[0170] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0171] Compounds of formula (XXVI) are commercially available.

[0172] Step b) Compounds of formula (XXIX) can be prepared in analogy to the method described in WO2007 / 090068. via amination using a compound of formula (XXVIII) in the presence of a base can be done.

[0173] Suitable bases are, for example, inorganic bases, such as carbonate bases. The solvent used is a polar non-protonated solvent. a rotic solvent, such as N,N-dimethylformamide or tetrahydrofuran; obtain.

[0174] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0175] Compounds of formula (XXVIII) are commercially available.

[0176] Step c) Compounds of formula (XXX) can be prepared in a manner similar to that described in WO2007 / 090068. The reaction can be carried out in the presence of a base. For example, sodium methoxide or potassium methoxide or sodium An alkoxide base such as sodium ethoxide or potassium ethoxide may be used. can.

[0177] Suitable solvents include protic solvents, e.g., short chain alcohols such as methanol or ethanol. It's a call.

[0178] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0179] Step d) The compound of formula (XXXI) can be prepared by the method described in Synthesis 1987, 6, 586-587, T etrahedron Letters 2006,47,565-567 or Che Similar to the method described in mMedChem 2010, 5, 65-78, XX) can be synthesized via hydrolysis.

[0180] Examples of suitable bases are, for example, lithium hydroxide or sodium hydroxide. The solvent may be polar aprotic and protic solvents and mixtures thereof, such as ethanol. The solvent may be toluene, tetrahydrofuran or water.

[0181] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0182] Step e) The compound of formula (XXXII) can be reacted with a compound of formula (II) in the presence of a condensing agent or a base. XXXI) can be prepared by reaction of the carboxylic acid

[0183] Compounds of formula (II) are commercially available or can be prepared by known methods, e.g., US2003 / 0122994. 003 / 069257, US2012 / 0319050, WO2011 / 107998 Alternatively, it can be prepared in a manner similar to that described in WO2010 / 91310.

[0184] Compounds of formula (II) are commercially available or can be prepared by known methods, e.g., US2 003 / 069257, US2012 / 0319050, WO2011 / 107998 or can be prepared by methods similar to those described in WO2010 / 91310.

[0185] The reaction of the compound of formula (II) with the carboxylic acid of formula (XXXI) can be carried out neat or in a solvent. in a solvent selected from conventional solvents which are inert under the general reaction conditions. It is preferred to carry out the reaction using ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons, such as dichloromethane ethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons, such as toluene or xylene; aprotic polar solvents, such as N,N-dimethylformamide or N -methylpyrrolidone, or nitrogen compounds such as pyridine are preferred.

[0186] Suitable condensing agents include, for example, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. Carbodiimides such as EDCI hydrochloride and 1,3-dicyclohexylcarbodiimide The preferred amines are thionyl chloride, thionyl chloride, and oxalyl chloride.

[0187] Suitable bases are the inorganic bases typically used in such reactions. or alkaline earth metal acetates, phosphates, carbonates and bicarbonates, for example. It is preferred to use a base selected from the following: Particularly preferred here is sodium acetate , sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, Sodium bicarbonate, potassium bicarbonate. Further preferred bases are alkali metal hydrides. , for example sodium hydride.

[0188] The reaction can be carried out under reduced pressure, normal pressure, or elevated pressure, and at temperatures between 0°C and 180°C. Preferably, the reaction is carried out at atmospheric pressure and at a temperature of 20 to 140°C.

[0189] Step f) The compound of formula (XXXIII) is condensed with the compound of formula (XXXII) in the presence of a base. It can be prepared by

[0190] The conversion to the compound of formula (XXXIII) can be carried out neat or in a solvent, and generally It is preferred to carry out the reaction in a solvent selected from conventional solvents which are inert under typical reaction conditions. Ethers, such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-Dimethoxyethane, tert-butyl methyl ether; Halogenated hydrocarbons, e.g. For example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chloroform. benzene; nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons solvents such as toluene or xylene; aprotic polar solvents such as N,N-dimethyl Preferred are methylformamide or N-methylpyrrolidone, or nitrogen compounds such as pyridine. Desirable.

[0191] Suitable bases are the inorganic bases typically used in such reactions. or alkaline earth metal acetates, phosphates, carbonates and bicarbonates, for example. It is preferred to use a base selected from the following: Particularly preferred here is sodium acetate , sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, Sodium bicarbonate and potassium bicarbonate.

[0192] The reaction can be carried out under reduced pressure, atmospheric pressure, or elevated pressure, and at temperatures between 0°C and 200°C. can be done.

[0193] Step g) The compound of formula (XXXIV) can be obtained by triflation of the hydroxy group in the presence of an auxiliary base. The compound of formula (XXXIII) can be synthesized as described in WO2011 / 075630. The triflating agent used can be, for example, triflate. It may be methylmethanesulfonic anhydride.

[0194] Suitable auxiliary bases are amine bases, such as triethylamine or Hunig's base, is another pyridine.

[0195] The reaction is carried out in a polar aprotic solvent such as pyridine, dichloromethane or tetrahydrofuran. It can be carried out in the presence of furan.

[0196] The reaction can be carried out under reduced pressure, atmospheric pressure, or elevated pressure, and at temperatures between 0°C and 200°C. can be done.

[0197] Step h) Compounds of formula (I) where n represents 0 can be prepared by catalyzing the reaction of compounds of formula (XXXIV) with a transition metal catalyst, CS Coupling was carried out in a manner similar to that described in WO2013 / 161853. It can be manufactured.

[0198] For example, palladium complexes such as Pd2(dba)3·CHCl3 are useful as catalysts. Suitable for use with amine bases, such as trialkylamines, or inorganic bases, such as carbonates. The base is suitable for use as an auxiliary base. Suitable solvents include polar aprotic solvents, e.g. For example, ether, tetrahydrofuran or 1,4-dioxane.

[0199] The reaction can be carried out under reduced pressure, atmospheric pressure, or elevated pressure, and at temperatures between 0°C and 200°C. can be done.

[0200] Step i) Compounds of formula (I) where n is 2 can be prepared by oxidizing compounds of formula (I) where n is 0. The oxidation is generally carried out in a solvent. For example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chloroform. Benzene; alcohols, such as methanol or ethanol; formic acid, acetic acid, propionic acid Alternatively, water is preferred.

[0201] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0202] The reaction is carried out under reduced, normal, or elevated pressure and at temperatures between -20°C and 120°C. It is possible.

[0203] Methods and Uses The present invention also provides compounds of formula (I) that act on pests and / or their habitats. The present invention relates to a method for controlling pests, which method allows the control of pests in agricultural and This is preferably carried out in the fields of human or animal protection. Methods for surgical or therapeutic treatment of the body, and diagnostic procedures performed on the human or animal body Exclude the diagnosis method.

[0204] The present invention further relates to compounds useful as pesticides, particularly as crop protection compositions. The present invention relates to the use of compounds of formula (I)

[0205] In the context of this application, the term "pesticide" is used in each case in combination with the term " The term "crop protection composition" always encompasses the term "crop protection composition".

[0206] The compounds of formula (I) are endowed with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility. compounds to protect plants and plant organs from biotic and abiotic stressors. to increase yields, improve the quality of harvested material, as well as agricultural , horticulture, animal husbandry, aquaculture, forestry, gardens and leisure facilities, protection of stored products and materials, and pests encountered in the sanitation sector, in particular insects, arachnids, helminths, especially nematodes and mollusks. Suitable for controlling animals.

[0207] In the context of this patent application, the term "hygiene" refers to the prevention of disease, especially infectious diseases. and to protect human and animal health and / or to protect the environment and / or to ensure cleanliness. should be understood to mean all the measures, rules and procedures that help maintain According to the invention, this is especially true for example of textiles or hard surfaces, in particular glass, wood Tables made of cement, porcelain, ceramic, plastic, or other metal(s) Cleaning procedures to ensure surfaces are free of hygiene pests and / or their secretions. The scope of protection of the invention in this respect preferably includes means for cleaning, disinfecting and sterilizing. refers to surgical or therapeutic procedures applied to the human or animal body, as well as to Excludes diagnostic procedures performed on the animal's body.

[0208] The term "sanitary department" refers to e.g. kitchens, bakeries, airports, bathrooms, swimming pools, department stores, Regarding hygiene in hotels, hospitals, stables, animal housing, etc., these hygiene measures, regulations and It encompasses all fields, technical fields and industrial applications where procedures are important.

[0209] The term "sanitary pests" therefore refers to organisms whose presence in the sanitary sector is of particular concern for health reasons. Therefore, the main purpose is to Avoid or minimize the presence of and / or exposure to sanitary pests in the gate. This is especially important for both the prevention of infestations and the prevention of existing infestations. This can be achieved by the use of pest control agents that can be used to prevent exposure to pests. It is also possible to use formulations that reduce or eliminate the presence of sanitary pests. This includes organisms that live in the ocean.

[0210] Therefore, the term "sanitary protection" refers to the extent to which these sanitary measures, regulations and procedures are maintained and / or It encompasses all actions that are or can be improved.

[0211] The compounds of formula (I) can preferably be used as pesticides. against normally susceptible and resistant species and against all or specific stages of development These pests include: Pests from the phylum Arthropoda, in particular the class Arachnida, e.g., Acarus Acarus spp., e.g., Acarus siro ), Aceria kuko, Aceria sheldonii sheldoni), Aculops spp., Aculus spp. Aculus spp., e.g., Aculus fock eui), Aculus schlechtendali ), Amblyomma spp., Amphitetranychus bifida Amphitetranychus viennensis, Argus genus Argas spp., Boophilus spp., Brevipalpus spp., e.g., Brevipalpus ho Brevipalpus phoenicis, Bryobia graminoum ( Bryobia graminum, Bryobia praethiosa (Bryobia p raetiosa), Centruroides spp., Chorioptes spp., Delmanisus gallinae rmanyssus gallinae), Dermatophagoides pteronyssinus (D ermatophagoides pteronyssinus), dermatophagoides Dermatophagoides farinae, Dermacent Dermacentor spp., Eotetranychus spp. nychus spp.), e.g., Eotetranychus hykoriae (Eotetran ychus hicoriae), Epitrimerus pili (Epitrimerus p yri), Eutetranychus spp., e.g. Eutetranychus banksi, Eliof Eriophyes spp., e.g., Eriophyes pili iophyes pyri), Glycyphagus domesticus (Glycyphagus domesticus), Halotydeus destorqutor (Halotydeus d estructor), Hemitarsonemus spp. .), for example, Hemitarsonemus latus )(=Polyphagotarsonemus l atus), Hyalomma spp., Ixodes spp. odes spp.), Latrodectus spp., Loxosceles spp., Neutrombicula autumna Squirrel (Neutrombicula autumnalis), Nufersa species (Nup hersa spp.), Oligonychus spp., e.g. For example, Oligonychus coffeae, oligo Oligonychus coniferarum, Oligo Oligonychus ilicis, Oligonychus indicus Oligonychus indicus, Oligonychus mangiferus igonychus mangiferus), Oligonychus pratensis (Oligonychus onychus pratensis), Oligonychus punicae (Oligonych us punicae), Oligonychus yot hersi), Ornithodorus spp., Ornithodorus Ornithonyssus spp., Panonychus spp. chus spp.), e.g., Panonychus citr i) (=Metatetranychus citri) , Panonychus ulmi (= Metatetranychus ulmi) Metatetranychus ulmi), Phyllocopterta oleivora ( Phyllocoptruta oleivora), Platytetranychus multizigii Tree (Platytetranychus multidigituli), Polyphago Polyphagotarsonemus latus, Pso Psoroptes spp., Rhipice phalus spp.), Rhizoglyphus spp. , Sarcoptes spp., Scorpio maurus rpio maurus), Steneotarsonem species us spp.), Steneotarsonemus spinki (Steneotarsonemu s spinki), Tarsonemus spp., e.g. Tarsonemus confusus, Tarsonemus Tarsonemus pallidus, Tetranychus species anychus spp.), e.g., Tetranychus canadensis (Tetranyc hus canadensis), Tetranychus cinnabarinus (Tetranych us cinnabarinus), Tetranychus turkestani (Tetranych us turkestani), Tetranychus urticae urticae), Trombicula alfre ddugesi), Vaejovis spp., Basateus ricinus Persisi (Vasates lycopersici); From the class Chilopoda, for example, the genus Geophilus s spp.), Scutigera spp.; of the order Collembola or class Collembola, e.g., Onychiurus Onychiurus armatus; Sminturus viridis inthurus viridis); From the class Diplopoda, for example, Braniurus guttulatus iulus guttulatus); Insecta, e.g., Blattodea, e.g., For example, Blatta orientalis, Blattara Blattella asahinai, Blattella germanica attella germanica), Leucophaea maderae (Leucopha ea maderae), Loboptera decipiens iens), Neostylopyga rhombifolia (Neostylopyga rhomb ifolia), Panchlora spp., Parcobratta spp. Parcoblatta spp., Periplaneta spp. spp.), e.g., Periplaneta americana (Periplaneta amer icana), Periplaneta australasiae (Periplaneta aust ralasiae), Pycnocelus surinamensis (Pycnoscelus surinamensis) inamensis), Supella longipalpa ); Coleoptera, e.g., Acalymma vitatum ma vittatum), Acanthoscelides obtectus (Acanthoscel ides obtectus), Adoretus spp., Ae Aethina tumida, Agelas tica alni), Agrilus spp., e.g. Agrilus planipennis, Agrilus coki Salis (Agrilus coxalis), Agrilus bilineatus (Agrilu s bilineatus), Agrilus anxiu s), Agriotes spp., e.g., Agriotes linn. Agriotes linneatus, Agriotes manx iotes mancus), Alphitobius diaperinus (Alphitobiu s diaperinus), Amphimaron solstitialis (Amphimall on solstitialis), Anobium punctatum (Anobium pu nctatum), Anoplophora spp., e.g. Anoplophora glabripennis ), Anthonomus spp., e.g., Anthonomus guineensis Rungis (Anthonomus grundis), Anthrenus species nus spp.), Apion spp., Apogonia spp. gonia spp.), Atomaria spp., e.g. Atomaria linearis, Att agenus spp.), Baris caerulescens ens), Bruchidius obtectus, Bruchus spp., e.g., Bruchus pisorum us pisorum), Bruchus rufimanu s), Cassida spp., Cero toma trifurcata, Ceutorrhynchu s spp.), e.g., Ceutorrhynchus assimilus (Ceutorrhynchus assimilis, Ceutorhynchus quadridens (Ceutorrhynch us quadridens), Ceutorrhynchu rapae s rapae), Chaetocnema spp., e.g. Chaetocnema confinis, Chaetocnema confinis Chaetocnema denticulata, Chaetocne Chaetocnema ectypa, Cleonus menzicus leonus mendicus), Conoderus spp. , Cosmopolites spp., e.g., Cosmopolites Cosmopolites sordidus, Costelita zea Costelytra zealundica, Ctenicella species icera spp.), Curculio spp., e.g. Curculio caryae, Curculio caryatripes (Curculio caryatrypes), Curculio obtusus (Curcu lio obtusus), Curculio sayi, Cryptolestes ferrugineus , Cryptolestes pusillus, Cryptolestes pusillus Cryptorhynchus lapathi, Cryptorhynchus lapathi Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus Cylindrocopturus adspersus ), Cylindrocopturus furni ssi), Dendroctonus spp., e.g. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp. tica spp.), e.g., Diabrotica b alteata), Diabrotica barberi , Diabrotica undecimpunctata howardii (Diabrotica undec impunctata howardi), Diabrotica undecimpunctata un Diabrotica undecimpunctata unde cimpunctata, Diabrotica virgifera virgifera (Diabro tica virgifera virgifera), Diabrotica virgifera Zeae (Diabrotica virgifera zeae), Dicocrosis spp. ( Dichocrocis spp.), Dicladistella armigera (Dicladisp a armigera), Diloboderus spp., Epicaerus spp., Epilachn a spp.), e.g., Epilachna borealis (Epilachna borealis is), Epilachna varivestis, E Epitrix spp., e.g., Epitrix cucumeris (E pitrix cucumeris), Epitrix fuscula (Epitrix fu scula), Epitrix hirtipennis s), Epitrix subcrinita, Epitrix Epitrix tuberis, Faustinus species tinus spp.), Gibbium psylloides es), Gnathocerus cornutus, He Hellula undalis, Heteronyx alatre teronychus arator), Heteronyx sp. p.), Hylamorpha elegans, Hiroto Hylotrupes bajulus, Hypera postica (H ypera postica), Hypomeces sq uamosus), Hypothenemus spp., e.g. , Hypothenemus hampei, Hypothenemus Obscurus (Hypothenemus obscurus), Hypothenemus pube Hypothenemus pubescens, Lachnosterna consanguinea Guinea (Lachnosterna consanguinea), Lacidderma se Serricorne (Lasioderma serricorne), Lateticus oryzae (L atheticus oryzae, Lathridius sp p.), Lema spp., Leptinotarsa ​​decemlineata inotarsa ​​decemlineata), Leucoptera species (Leucopte ra spp.), e.g., Leucoptera cof feella), Limonius ectypus, Li Lissorhoptrus oryzophilus ), Listronotus spp. (=Hyperodes spp. (H yperodes spp.), Lixus spp., Ruperodes spp. species (Luperodes spp.), Luperomorpha xanthodera (Lupero orpha xanthodera), Lyctus spp., Mega Megacyllene spp., e.g., Megacyllene robiniae ( Megacyllene robiniae), Megascelis sp. spp.), Melanotus spp., e.g., Melanotus Melanotus longulus oregonensis (Melanotus longulus oregon ensis), Meligethes aeneus, Melo Melolontha spp., e.g., Melolontha melolonta (M elolontha melolontha), Migdolus species (Migdolus s pp.), Monochamus spp., Naupactus xanthus tographus (Naupactus xanthographus), Necrobia species (N ecrobia spp.), Neogalerucella spp. pp.), Niptus hololeucus, Oryctes Oryctes rhinoceros, Oryzaephilus surina Oryzaephilus surinamensis, Oryzafagus oryzae (Oryzaphagus oryzae), Otiorhynchus species hynchus spp.), e.g., Otiorhynchus cribricollis (Otiorh ynchus cribricollis), Othiorhynchus ligusticii (Otior hynchus ligustici), Otiorhynchus ovatus (Otiorhyn chus ovatus), Otiorhynchus rugosostialus (Otiorhync hus rugosostriarus), Othiorhynchus sulcatus (Otiorh ynchus sulcatus), Oulema spp., e.g. , Oulema melanopus, Oulema oryzae ( Oulema oryzae, Oxycetonia jukunda jucunda, Phaedon cochleari ae), Phyllophaga spp., Phyllophaga here Phyllophaga helleri, Phyllotreta species eta spp.), e.g., Phyllotreta armolasiae (Phyllotreta armoraciae), Phyllotreta pusi lla), Phyllotreta ramosa, Phyllotreta Phyllotreta striolata, Popilia japonica Popillia japonica, Premnotrypes species trypes spp.), Prostephanus toruncatus (Prostephanu s truncatus), Psylliodes spp., e.g. For example, Psylliodes affinis, Psylliodes Psylliodes chrysocephala, Psylliodes chrysocephala Psylliodes punctulata, Putinus species (Ptinus spp.), Rhizobius ventralis (Rhizobius ven t ralis), Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugi Neus (Rhynchophorus ferrugineus), Rhynchophorus pallus Palmarum (Rhynchophorus palmarum), Scol ytus spp.), e.g., Scolytus multistriatus (Scolytus multistriatus), Sinoxylon perforans (Sinoxylon p erforans), Sitophilus spp., e.g. Sitophilus granarius, Sitophilus Sitophilus linearis, Sitophilus oryzae Sitophilus oryzae, Sitophilus zeamais ilus zeamais), Sphenophorus spp. .), Stegobium paniceum, Sterne Sternechus spp., e.g., Sternechus pardatus (S ternechus paludatus), Symphyletes species es spp.), Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymecus Tanymecus indicus, Tanymecus pariatus ymecus palliatus), Tenebrio molitor (Tenebrio molitor) litor), Tenebrioides mauretanicus (Tenebrioides mau retanicus), Tribolium spp., e.g. Tribolium audax, Tribolium castanea Neum (Tribolium castaneum), Tribolium confusum (Tr ibolium confusum), Trogoderma sp. p.), Tychius spp., Xylotrex spp. rechus spp.), Zabrus spp., e.g. Zabrus tenebrioides; Dermaptera, for example, Anisolabis maritime isolabis maritime), Forficula auricularia (Forfic ula auricularia), Labidura ripa ria); From the order Diptera, for example, Aedes spp., e.g. For example, Aedes aegypti, Aedes albopictus Aedes albopictus, Aedes st icticus, Aedes vexans, Agromyza spp. Species (Agromyza spp.), e.g., Agromyza frontera (Agromyz a frontella), Agromyza parvicornis (Agromyza parv icornis), Anastrepha spp., Anophe Anopheles spp., e.g., Anopheles quadrimaculatus Anopheles quadrimaculatus, Anopheles gumbia Anopheles gambiae, Asphondyl ia spp.), Bactrocera spp., e.g. Bactrocera cucurbitae, Bactro Bactrocera dorsalis, Bactrocera olea Bactrocera oleae, Bibio hortulanus tulanus), Calliphora erythrocephala (Calliphora erythr ocephala), Calliphora vicina, Sera Ceratitis capitata, Chilonomus species ronomus spp., Chrysomya spp., chestnut Chrysops spp., Chrysozona pluvialis zona pluvialis), Cochliomya spp. ), Contarinia spp., e.g., Contarinia di Johnsoni (Contarinia johnsoni), Contarinia nasturtii ( Contarinia nasturtii, Contarinia pirivora (Contar inia pyrivora), Contarinia scurge (Contarinia scurge) hulzi), Contarinia sorghicol a), Contarinia tritici, Cordylobus Cordylobia anthropophaga, Crico Cricotopus sylvestris, genus Cricotopus Species (Culex spp.), e.g., Culex pipiens (Culex pipiens) ns), Culex quinquefasciatus (Culex quinquefascia tus), Culicoides spp., Culicateta spp. liseta spp.), Cuterebra spp., Dacus Dacus oleae, Dasineura spp. .), for example, Dasineura brassicae, Delia spp., e.g., Delia anthracnose tiqua), Delia coarctata, Delia f Delia florilega, Delia pla tura), Delia radicum, Dermatobia hominis Dermatobia hominis, Drosophila species a spp.), e.g., Drosophila melanogaster (Drosphila melanogaster) anogaster, Drosophila suzuki i), Echinocnemus spp., Eureia hera Clay (Euleia heraclei), Fannia spp. ), Gasterophilus spp., Glossina spp. (Glossina spp.), Haematopota spp. .), Hydrellia spp., Hydrellia griseola (H ydrellia griseola), Hylemya spp., Hippobosca spp., Hypoderma spp. rma spp.), Liriomyza spp., e.g., Liriomyza Liriomyza brassicae, Liriomyza huid Liriomyza huidobrensis, Liriomyza sativae (Liriomyza sativae), Lucilia spp. , e.g., Lucilia cuprina, Lutozomyia spp. (Lutzomyia spp.), Mansonia spp., Musca spp., e.g., Musca domestica mestica), Musca domestica v icina), Oestrus spp., Ocinella fritillaria (O scinella frit), Paratanytarsus species spp.), Paralauterborniella subcinctum (Paralauterborniella subcinctum iella subcincta, Pegomia or Pegomia species (Pegomya or Pegomyia spp.), e.g., Pegomyia bettae (Pegomya b etae), Pegomya hyoscyami, Pegomya Rubibora (Pegomya rubivora), Phlebottomus species omus spp.), Phorbia spp., Phormia spp. hormia spp.), Piophila casei, Platyparea poeciloptera, Platyparea Prodiplosis spp., Psila rosae rosae), Rhagoletis spp., e.g. Rhagoletis cingulata, Rhagoletis comp Leta (Rhagoletis completa), Rhagoletis fausta (Rhag oletis fausta), Rhagoletis indigestion (Rhagoletis indifferens), Rhagoletis mendakis dax), Rhagoletis pomonella, monkey Sarcophaga spp., Simulium spp. spp.), e.g., Simulium meridio nale), Stomoxys spp., Tabanus spp. nus spp.), Tetanopus spp., Chipla spp. Tipula spp., e.g. Tipula paludos a), Tipula simplex, Toxotrypana cruzi Bicauda (Toxotrypana curvicauda); Hemiptera, e.g., Aciascia ebayleiana Acizzia acaciaebaileyanae, Acizzia dodonaeae (Acizzia dodonaeae), Acizzia uncatatoides (Acizzia uncatoides), Acrida turrita, reed Acyrthosiphon spp., e.g., Acyrthosiphon pi Acyrthosiphon pisum, Acrogonia species ia spp.), Aeneolamia spp., Agonose Agonoscena spp., Aleurocanthus spp. nthus spp.), Aleyrodes prole tella), Aleurolobus barodensis (Aleurolobus barode nsis), Aleurothrix flocc osus), Allocaridara malayensis (Allocaridara malaye nsis), Amrasca spp., e.g., Amrasca vig Amrasca bigutulla, Amrasca devastans ca devastans, Anuraphis card ui), Aonidiella spp., e.g., Aonidiella Aonidiella aurantii, Aonidiella citrina (Aonidiella citrina), Aonidiella inornata (Aonidi ella inornata), Aphanostigma pili (Aphanostigma piri), Aphis spp., e.g., Aphis citricola ( Aphis citricola, Aphis cracci vora), Aphis fabae, Aphis holvesi Aphis forbesi), Aphis glycines , Aphis gossypii, Aphis hederae is hederae), Aphis illinois ensis), Aphis middletoni, Aphis Aphis nasturtii, Aphis nerii nerii), Aphis pomi, Aphis spiraecola phis spiraecola), Aphis vivulniphila rniphila), Arborizia apicali s), Arytainilla spp., Aspidiella spp. spidiella spp.), Aspidiotus spp. .), e.g., Aspidiotus nerii, Atanu Atanus spp., Aulacorthum solani solani), Bemisia tabaci, Blastopsi Blastopsylla occidentalis, Bole Boreioglycaspis melaleucae ae), Brachycaudus helichrys i), Brachycolus spp., Brevicoryne brushii Brevicoryne brassicae, Cacops spp. ylla spp., e.g., Cacopsylla pyricola icola), Calligypona marginata ), Capulinia spp., Carneocephala fulgida ( Carneocephala fulgida), Ceratobaccuna lanigera (Cerat ovacuna lanigera), Cercopidae, Cerops Ceroplastes spp., Chaetosiphon fragaehorii ( Chaetosiphon fragaefolii), Chionaspis tegalensis ( Chionaspis tegalensis, Chlorita onukii a onukii), Chondracris rosea Chromaphis juglandicola ), Chrysomphalus aonidum, Chrysomphalus ficus, Ficus sativus Mbira (Cicadulina mbila), Cocco mytilus harii (Cocco mytilus halli), Coccus spp., e.g. Coccus hesperidum, Coccus longuls (Coccus longulus), Coccus pseudomagnoliarum (Coccu s pseudomagnoliarum), Coccus viridis (Coccus viridis) ridis), Cryptomyzus ribis, Cryptoneossa spp., Cte narytaina spp.), Dalbulus spp., Dialeurodes chittendeni, Dialeurodes chittendeni Dialeurodes citri, Diaphorina citri (D iaphorina citri), Diaspis spp., Diuraphis spp., Doralis spp. pp.), Drosicha spp., Dysap his spp.), e.g., Dysaphis apii folia), Dysaphis plantagine a), Dysaphis tulipae, Dysmicoccus spp. species (Dysmicoccus spp.), Empoasca sp p.), e.g., Empoasca abrupta, Empoasca fabae, Empoasca marigna mpoasca maligna), Empoasca solana (Empoasca sol ana), Empoasca stevensi, Elio Eriosoma spp., e.g., Eriosoma americanum osoma americanum), Eriosoma lanigerum (Eriosoma l anigerum), Eriosoma pyricola, Erythroneura spp., Eucalyptolima spp. Eucalyptolyma spp., Euphyllura spp. spp.), Euscelis bilobatus, Ferrisia spp., Fiorinia spp. pp.), Furcaspis oceanica, Geo Geococcus coffeae, Glycaspis species (G lycaspis spp.), Heteropsylla cubana (Heteropsylla c ubana), Heteropsylla spinulosa (Heteropsylla spinulo sa), Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus arundinis Hyalopterus pruni, Icer ya spp.), e.g., Icerya purchasi, Idiocerus spp., Idioscops spp. copus spp.), Laodelphax striatellus striatellus), Lecanium spp., e.g. Lecanium corni (= Parthenolecanium corni) (Parthenolecanium corni), Lepidosafes species (Lepi dosaphes spp.), e.g., Lepidosap ulmi hes ulmi), Lipaphis erysimi, Lopholeucaspis japonica, Li Lycorma delicatula, Macrosiphum species (M acrosiphum spp.), e.g., Macrosiphum euphorbiae (Macr osiphum euphorbiae, Macrosiph lily um lilii), Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melan aphis sacchari), Metcalfiella species spp.), Metcalfa pruinosa, Metcalfa Metopolophium dirhodum, Moneria Monellia costalis, Monelliopsis pecanis (M onelliopsis pecanis), Myzus spp., e.g. For example, Myzus ascalonicus, Myzus sera Myzus cerasi, Myzus ligustri ), Myzus ornatus, Myzus persicae us persicae), Myzus nicotianae ), Nasonovia ribisnigri, Neoma Neomaskellia spp., Nephthochichis spp. otettix spp.), e.g., Nephot ettix cincticeps), Nephotettix nigropictus (Nephot ettix nigropictus), Nettigonycera spectre (Nettigon iclla spectra), Nilaparvata lugens (Nilaparvata l ugens), Oncometopia spp., Orthesia Orthezia praelonga, Oxya chinensis xya chinensis), Pachypsylla spp. , Parabemisia myricae, Paratoliosa Paratrioza spp., e.g., Paratrioza cockleri (Par atrioza cockerelli), Parlatoria species spp.), Pemphigus spp., e.g., Pemphigus Pemphigus bursarius, Pemphigus potpourri Pemphigus populivenae, Peregrinus myzis (P eregrinus maidis), Perkinsiella species spp.), Phenacoccus spp., e.g. Eh Phenacoccus madeirensis, Phenacoccus madeirensis Phloeomyzus passerinii, Holo Phorodon humuli, Phylloxera species era spp.), e.g., Phylloxera devastratrix (Phylloxer a devastatrix, Phylloxera notabilis (Phylloxera n otabilis), Pinnaspis aspidistrae (Pinnaspis aspi distrae), Planococcus spp., e.g. , Planococcus citri, Prosopidopsilla Flava (Prosopidopsylla flava), Protopulvinaria pili Protopulvinaria pyriformis, Pseudaulaka Pseudaulacaspis pentagona, Pseudaulacaspis pentagona Pseudococcus spp., e.g., Pseudococcus Pseudococcus calceolariae, Pseudo Pseudococcus comstocki, Pseudo Pseudococcus longispinus, P Pseudococcus maritimus, Pseudococcus Pseudococcus viburni, Psilopsis Psyllopsis spp., Psylla spp., e.g. For example, Psylla buxi, Psylla mali, li), Psylla pyri, Pteroma lus spp.), Pulvinaria spp., Pillira spp. Pyrilla spp., Quadraspidi spp. otus spp.), e.g., Quadraspiziotus juglansregiae (Qua draspidiotus juglansregiae), Quadraspidiotus o Streaeformis (Quadraspidiotus ostreaeformis) , Quadraspidiotus perniciosus (Quadraspidiotus perniciosus iciosus), Quesada gigas, Lastrocock Rastrococcus spp., Rhopalos iphum spp.), e.g., Rhopalosiphum mays (Rhopalosiphu m maidis), Rhopalosiphum oxyacanthae (Rhopalosiphum oxyacanthae), Rhopalosiphum pad i), Rhopalosiphum rufiab dominale), Saissetia spp., e.g. Saissetia coffeae, Saissetia miranda ( Saissetia miranda), Saissetia neglecta (Saissetia neglecta), Saissetia oleae, Scaphoideus titanus, Scaphoideus titanus Graminum (Schizaphis graminum), Serenaspizus alticula Selenaspidus articulatus, Sip flava ha flava), Sitobion avenae, Soga Sogata spp., Sogatella f urcifera), Sogatodes spp., Stictoceph Stictocephala festina, Siphoninus fi Lileae (Siphoninus phillyreae), Tenarafala maraien sis (Tenalaphara malayensis), Tetragonocephala species (T etragonocephela spp.), Tinocallis cariaehoriae (Tin ocallis caryaefoliae), Tomaspis spp. pp.), Toxoptera spp., e.g., Toxoptera Toxoptera aurantii, Toxoptera citrinoides Toxoptera citricidus, Trialeurodes vaporariorum (Trialeurodes vaporariorum), Trioz species a spp.), e.g., Trioza diospyri, Typhlocyba spp., Unaspis spp. spp.), Viteus vitifolii, Zigina spp. Species (Zygina spp.); The suborder Heteroptera, for example, Aelia species spp.), Anasa tristis, Anthethiopsis Antestiopsis spp., Boisea spp. ), Blissus spp., Calocoris spp. spp.), Campylomma livida, Cabela Cavelerius spp., Cimex spp. ), for example, Cimex adjunctus, Cimex hemipterus, Cimex rectularius Cimex lectularius), Cimex pilocellus sellus), Collaria spp., Creonthiades di Creontiades dilutus, Dasyn piperis us piperis), Dichelops furcatus us), Diconocoris hewetti, Diconocoris Dysdercus spp., Euschis spp. tus spp.), e.g., Euschistus herus os), Euschistus servus, Euski Euschistus tristigmus, Euschistus Euschistus variolarius, Eurydema Eurydema spp., Eurygaster spp. pp.), Halyomorpha halys, Heliopa Heliopeltis spp., Horcius nobilis ias nobilellus), Leptocorisa spp. .), Leptocorisa varicornis , Leptoglossus occidentalis (Leptoglossus occidenta lis), Leptoglossus phyllopu s), Lygocoris spp., e.g., Lygocoris pubblica Lygocoris pabulinus, Lygus spp. ), for example, Lygus elisus, Lygus hesperus ygus hesperus, Lygus lineolaris is), Macropes excavatus, Mega Megacopta cribraria, Myridae (Mir idae), Monalonion atratum, Ne Nezara spp., e.g., Nezara viridis ridula), Nysius spp., Oeba lus spp.), Pentomidae, Piesma quadrata ( Piesma quadrata, Piezodorus spp. .), for example, Piezodorus guildini i), Psallus spp., Pseudacis persea udacysta persea), Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotino Scotinophora spp., Stephanitis pear anitis nashi), Tibraca spp., Triatoma Genus and species (Triatoma spp.); Hymenoptera, for example, Acromyrmekis species yrmex spp.), Athalia spp., e.g. Athalia rosae, Atta spp., Camellia sinensis Camponotus spp., Dolichovespula spp. ovespula spp.), Diprion spp., e.g. , Diprion similis, Hoplocampa species plocampa spp.), e.g., Hoplocampa kookei (Hoplocamp a cookei), Hoplocampa testuginea (Hoplocampa testu dinea), Lasius spp., Linepithema (Iridiomyrm Kiss) · Humire (Linepithema (Iridiomyrmex) humil e), Monomorium pharaonis, Pa Paratrechina spp., Paravespra spp. vespula spp.), Plagiolepis spp. ), Sirex spp., e.g., Sirex noctilio x noctilio), Solenopsis invicta (Solenopsis invi cta), Tapinoma spp., Technomyrmecides albipe Technomyrmex albipes, Urocerus species Vespa spp., e.g., Vespa crabro spa crabro), Wasmannia auropunctata (Wasmannia au ropunctata), Xeris spp.; Isopoda, e.g., Armadillidium vulgare (Arm adillidium vulgare, Oniscus acellus sellus), Porcellio scaber; From the order Isoptera, for example, Coptote rmes spp.), e.g., Coptotermes formosanus (Coptotermes s formosanus), Cornitermes cumulans cumulans), Cryptotermes spp., Incisitermes spp., Calotermes spp. alotermes spp.), Microtermes obesi (Microtermes obesi), Nasutitermes spp., Odonto Odontotermes spp., Porottermes spp. ermes spp.), Reticulitermes sp. p.), e.g., Reticulitermes flavipes (Reticulitermes flavipes) avipes), Reticulitermes hesperus sperus); Lepidoptera, e.g., Achr oia grisella), Acronicta majo r), Adoxophyes spp., e.g., Adoxophyes Adoxophyes orana, Ae leucomelas dia leucomelas), Agrotis spp., e.g. For example, Agrotis segetum, Agrotis epsilon Agrotis ipsilon, Alabama spp., For example, Alabama argillacea, Amiello Amyelois transitella, Anarsia species ( Anarsia spp., Anticarsia spp. For example, Anticarsia gemmatalis s), Argyroploce spp., Autographa spp. (Autographa spp.), Barathra brassicae (Barathra br assicae), Blastodacna atra, Bo Borbo cinnara, Buccleuchus tulbergii (B ucculatrix thurberiella), Bupaceae piniarius (Bup alus piniarius), Busseola spp., Cacoecia spp., Caloptilia teivora ilia theivora), Capua reticulana a), Carpocapsa pomonella, Carpo Carposina niponensis, Carposina niponensis rumata (Cheimatobia brumata), Chilo spp. ), for example, Chilo plejadellus, Chilo s pressalis (Chilo suppressalis), Coleucis pariana (Ch oreutis pariana), Choristoneura sp. spp.), Chrysodeixis chalci tes), Clysia ambiguella, Kunafa Cnaphalocerus spp., Cnaphalocerus medina Squirrel (Cnaphalocrocis medinalis), Cnaphalocrocis species (Cn ephasia spp.), Conopomorpha spp. .), Conotrachelus spp., Copitarsia spp. species (Copitarsia spp.), Cydia spp., e.g. , Cydia nigricana, Cydia pomonella ia pomonella), Dalaca noctuide s), Diaphania spp., Diparopsis spp. aropsis spp.), Diatraea saccharalis (Diatraea sac charalis), Dioryctria spp., e.g. , Dioryctria zimmermani, Air Earias spp., Ecdytropha aurantium olopha aurantium), Elasmopalpus lignocellus (Elasmo palpus lignosellus), Eldana saccharina (Eldana sa ccharina), Ephestia spp., e.g., Ephestia Ephestia elutella, Ephestia queni Ephestia kuehniella, Epinotia species spp.), Epiphyas postvitta na), Erannis spp., Oerskobiella musculana ( Erschoviella musculana), Etiella species (Etiella s pp.), Eudocima spp., Eulia spp. spp.), Eupoecilia ambiguera (Eupoecilia ambigue lla), Euproctis spp., e.g. Euproctis chrysorrhoea, Euproctis chrysorrhoea Euxoa spp., Feltia spp., Galleria Galleria mellonella, Gracilaria species llaria spp.), Grapholitha spp., e.g. For example, Grapholita molesta, Grapholita Grapholita prunivora, Hedy lepta spp.), Helicoverpa spp., e.g. For example, Helicoverpa armigera, Helicoverpa Helicoverpa zea, Helioth is spp.), e.g., Heliothis virescens cens), Hofmannophila pseudospretella (Hofmannophila p seudospretella), Homoeosoma spp. ), Homona spp., Hyponomeuta padera uta padella), Kakivoria flavofasiata (Kakivoria flavofasiata) avofasciata), Lampides spp., Rafig Laphygma spp., Laspeyresia molesta sia molesta), Leucinodes orbonaris bonalis), Leucoptera spp., e.g. Leucoptera coffeella, Lithocoelechis Lithocolletis spp., e.g., Lithocolletis brancalde Lithocolletis blancardella, Lithophane antennus Lithophane antennata, Lobesia species spp.), e.g., Lobesia botrana, Loxa Loxagrotis albicosta, Lymantria Lymantria spp., e.g., Lyman tria dispar), Lyonetia spp., e.g. Lyonetia clerkella, Malacosoma neu Malacosoma neustria, Malca testularis uca testulalis), Mamestra brassicae (Mamestra bra ssicae), Melanitis leda, Mosis species (M ocis spp.), Monopis obviella, Mythimna separata, Nemapogon croacer Nemapogon cloacellus, Nymphula species spp.), Oiketicus spp., Onphysa spp. mphisa spp.), Operophtera spp., Oria spp., Orthaga spp., male Ostrinia spp., e.g., Ostrinia nubilalis (O strinia nubilalis), Panolis flammare ammea, Parnara spp., Pectinophora spp. tinophora spp.), e.g., Pectinophora gossypiera (Pectin ophora gossypiella), Perileucoptera species (Perileuco ptera spp.), Phthorimaea spp., e.g. For example, Phthorimaea operculella ), Phyllocnistis citrella, Phyllonorycter spp., e.g., Phyllonorycter Phyllonorycter blancardella ), Phyllonorycter crataegera ella), Pieris spp., e.g., Pieris rapae (P ieris rapae), Platynota stultana ana), Plodia interpunctella a), Plusia spp., Plutela xylostella lla xylostella)(=Plutella macripennis (Plutella m aculipennis), Podesia spp., e.g. Podesia syringae, Prays species spp.), Prodenia spp., Protoparce spp. rotoparce spp.), Pseudaletia sp. p.), for example, Pseudaletia unipuncta (Pseudaletia unipu ncta), Pseudoplusia incl udens), Pyrausta nubilalis, La Rachiplusia nu, Schoen obius spp.), e.g., Schoeno bius bipunctifer), Scirpophaga spp. pp.), e.g., Scirpophaga innota ta), Scotia segetum, Sesamia species amia spp., e.g., Sesamia inferens rens), Sparganothis spp., Spodoptera Spodoptera spp., e.g., Spodoptera ellagiana (Sp odoptera eradiana), Spodoptera exigua (Spodopte ra exigua), Spodoptera frugiperda iperda), Spodoptera praefica a), Stathmopoda spp., Stenoma spp. noma spp.), Stomopteryx subsesibella (Stomopteryx s ubsecivella), Synanthedon spp., Tecia solanivora, Thaumetpoea species aumetopoea spp.), Thermesia gemmatalis (Thermesia gemmatalis), Tinea cloacella, Tinea pellionella, Tinea bisselliera ( Tineola bisselliella), Tortrix spp. p p.), Trichophaga tapetzella , Trichoplusia spp., e.g., Trichoplusia Trichoplusia ni, Trypo ryza incertulas), Tuta absoluta , Viracola spp.; Orthoptera or Saltatoria For example, Acheta domesticus, Dicrop Dichroplus spp., Gryllotalpa spp. pa spp.), e.g., Gryllotalpa gryllotalpa (Gryllotalpa g ryllotalpa), Hieroglyphus spp. , Locusta spp., e.g., Locusta migratoria (Lo custa migratoria), Melanoplus sp. p.), e.g., Melanoplus devasta tor), Paratlanticus ussuriensis (Paratlanticus ussu riensis), Schistocerca gregaria (Schistocerca greg aria); From the order Phthiraptera, for example, Damalinia species nia spp.), Haematopinus spp., Linognathus spp., Pediculus spp. lus spp.), Phylloxera vastatrix atrix), Phthirus pubis, Trichodectes spp. Species (Trichodectes spp.); From the order Psocoptera, for example, Lepinnotus species otus spp.), Liposcelis spp.; From the order Siphonaptera, for example, Ceratophilus species ophyllus spp.), Ctenocephalid es spp.), e.g., Ctenocephalides canis (Ctenocephalid es canis), Ctenocephalides felis (Ctenocephalides felis), Pulex irritans, Tunga pe Tunga penetrans, Xenopsilla cheopis sylla cheopis); Thysanoptera, e.g., Anaphotryps obscu Anaphothrips obscurus, Variothrips biformis ( Baliothrips biformis), Caetanahothrips leeuweni (C haetanaphothrips leeuweni), Drepanothrips leeutheri (Drepanothrips reuteri), Enneothrips flavens (E nneothrips flavens), Frankliniella species ella spp.), e.g., Frankliniell fusca (Frankliniell a fusca), Frankliniella occidentalis (Frankliniella occidentalis), Frankliniella scullzei (Franklini ella schultzei), Franklinieella tritici (Franklinie lla tritici), Frankliniella bassinii (Frankliniella vaccinii), Frankliniella williamsii (Frankliniella williamsi), Haplothrips spp., Heliothrips spp., Heliothrips femo Hercinothrips femoralis, Ka kothrips spp.), Rhipipho rothrips cruentatus), Scirtothrips species ips spp.), Taeniothrips cardamomum (Taeniothrips ca rdamomi), Thrips spp., e.g., Thrips pal. Thrips palmi, Thrips tabaci; Zygentoma (=Thysanura), e.g., Ctenolepis Ctenolepisma spp., Lepism saccharina a saccharina), Lepismodes inquilinus (Lepismodes inquilinus), Thermobia domestica (Thermobia domest ica); From the class Symphyla, for example, Scutiger species ella spp.), e.g., Scutigerella inmaculata (Scutigerell a immaculata); Pests of the phylum Mollusca, e.g., Bivalvia ia), for example, Dreissena spp.; and Gastropoda, for example, Arion spp. pp.), e.g., Arion ater rufus, Biomphalaria spp., Bul inus spp.), Deroceras spp., e.g. Deroceras laeve, Galba sp. p.), Lymnaea spp., Oncomelania spp. melania spp.), Pomacea spp., Succinea Genus and species (Succinea spp.); Plant pests of the phylum Nematoda, i.e. plant-parasitic nematodes, in particular Aglenchus spp., e.g., Aglenchus agleco Aglenchus agricola, Anguina sp p.), e.g., Anguina tritici, Aphele Aphelenchoides spp., e.g., Aphelenchoides Death arachidis (Aphelenchoides arachidis), Aphelen Aphelenchoides fragariae, Vero Belonolaimus spp., e.g., Belonolaimus guineensis Lacilis (Belonolaimus gracilis), Belonolaimus longica Udatus (Belonolaimus longicaudatus), Belonolaimus · Belonolaimus nortoni, Bursaphelenchus species ( Bursaphelenchus spp.), e.g., Bursaphelenchus cocophii Rus (Bursaphelenchus cocophilus), Bursaphelenchus Bursaphelenchus eremus Xylophilus (Bursaphelenchus xylophilus), Cacopow Cacopaurus spp., e.g., Cacopaurus pestis (Ca copaurus pestis), Criconemella spp. pp.), for example, Criconemella curvata a), Criconemella onoensis, Criconemella ornata, Criconemella Criconemella rusium, Criconemella xenoplakia Criconemella xenoplax (=Mesocriconemella xenoplax) Mesocriconema xenoplax), Criconemoides species (Cr iconemoides spp.), e.g., Criconemoides ferniae (Cr iconemoides ferniae), Criconemoides onoense (Cric onemoides onoense, Criconnemoides ornatum (Cricon emoides ornatum), Ditylenchus sp. p.), e.g., Ditylenchus dipsaci , Dolichodorus spp., Globodera spp. bodera spp.), e.g., Globodera pallida (Globodera pal lida), Globodera rostochiensis (Globodera rostochie nsis), Helicotylenchus spp., e.g. For example, Helicotylenchus dihystera era), Hemicriconemoides spp. ), Hemicycliophora spp., Heterodera Heterodera spp., e.g., Heterodera avenae (Heter odera avenae), Heterodera gly cines), Heterodera schachtii , Hirschmaniella spp., Hoplolimus Hoplolaimus spp., Longidorus spp. spp.), e.g., Longidorus afri canus), Meloidogyne spp., e.g., Melo Meloidogyne chitwoodi, Meloidogyne Meloidogyne fallax, Meloidogyne hapula (M eloidogyne hapla), Meloidogyne incognita (Meloidog Meloinema spp., Meloinema incognita, Nacobbus spp., Neotylencus spp. chus spp.), Paralongidorus spp. .), Paraphelenchus spp., Paratricos Paratrichodorus spp., e.g., Paratrichodorus Paratrichodorus minor, Paratylenchus species ratylenchus spp.), Pratylenchus spp. spp.), e.g., Pratylenchus penetrans (Pratylenchus p enetrans), Pseudohalenchus sp. p.), Psilenchus spp., Punctodera spp. unctodera spp.), Quinisulcius spp. spp.), Radopholus spp., e.g., Radopholus Radopholus citrophilus, Radopholus citrophilus Milis (Radophorus similis), Rotyle spp. nchulus spp.), Rotylenchus spp. , Scutellonema spp., Su banguina spp.), Trichodorus spp. ), for example, Trichodorus obtusus, Trichodorus primitivus, Chile Tylenchorhynchus spp., e.g., Tylenchorhynchus Lynx annulatus (Tylenchorhynchus annulatus), Tylenchulus spp., e.g., Tylenchulus cicada Penetrans (Tylenchulus semipenetrans), Xyphinema Genus species (Xiphinema spp.), e.g., Xiphinema index (Xiph inema index).

[0212] The compounds of formula (I) may act as herbicides, safeners, As growth regulators or agents for improving plant properties, microbicide as fungicides or gametocides, e.g. icides, antifungals (antimycotics), bactericides ides), virucides (including agents against viroids) or as MLOs (Male Lung Cancer Ointments). It can be used as an agent against rickettsia-like organisms (RLO) and rickettsia-like organisms (RLO). They may also be intermediates or precursors for the synthesis of other active compounds. It can also be used as a body.

[0213] formulation The present invention further provides a pesticide comprising at least one compound of formula (I): Formulations as pesticides and application forms prepared from the formulations (e.g., drench solutions, drip solutions) and spray solutions. The use forms optionally contain further pesticides and / or Alternatively, adjuvants that improve the effect, such as penetrating agents, for example, vegetable oils (e.g., naphthalene, Seed oil, sunflower oil), mineral oil (e.g., paraffin oil), vegetable fatty acid alkyl ester (e.g., rapeseed oil methyl ester or soybean oil methyl ester), or alkano alkyl alkoxylates, and / or spreading agents, e.g., alkyl siloxanes and and / or salts, such as organic or inorganic ammonium or phosphonium salts (e.g. , ammonium sulfate or diammonium hydrogen phosphate), and / or a retention promoter ( retention promoter) (e.g., dioctyl sulfosuccinate or hydroxypropyl guar polymer), and / or a humectant (e.g., glycerol) , and / or fertilizers (e.g., ammonium-containing fertilizers, potassium-containing fertilizers or phosphorus-containing fertilizers) Contains fertilizer.

[0214] Conventional formulations include, for example, aqueous solutions (SL), emulsifiable concentrates (EC), oil-in-water emulsions, emulsions in water (EW), suspension concentrates (SC, SE, FS , OD), water dispersible granule (WG), granule (GR), and capsule concentrate (capsul These and other possible formulations are are described, for example, in: Crop Life International nal and in Pesticide Specifications, Man ual on development and use of FAO and WH O specifications for pesticides,FAO Plan t Production and Protection Papers-173 Manufacturer: the FAO / WHO Joint Meeting on Pesticid e Specifications, 2004, ISBN: 9251048576). Applicable The formulations may contain, in addition to one or more compounds of formula (I), optionally further pesticidal active ingredients. Contains minutes.

[0215] Adjuvants, such as extenders, solvents, spontaneous promoters ter), carrier, emulsifier, dispersant, frost protection agent gent), biocides, thickeners and / or other auxiliary agents, e.g., adjuvants In this context, adjuvants are preferred in formulations or forms of use in which Ingredients that enhance a biological effect but do not themselves have a biological effect Examples of adjuvants are compounds that promote retention, spreading, and adhesion to the leaf surface. These agents are either activating agents or penetration enhancing agents.

[0216] These preparations can be prepared in a known manner, for example by incorporating a compound of formula (I) into an adjuvant, e.g. Bulking agents, solvents and / or solid carriers, and / or other auxiliary agents, such as surfactants, Such preparations are manufactured in suitable equipment or Or, prepare it before or during application.

[0217] The adjuvants used may be formulations of the compounds of formula (I) or formulations prepared from such formulations. Use forms, such as ready-to-use pesticides, e.g. For example, if the spray or seed dressing product has special properties, e.g., specific physical or technical characteristics and / or may be a substance suitable for imparting biological properties, etc.

[0218] Suitable extenders are, for example, water, polar and non-polar organic and chemical liquids, e.g., aromatic and and non-aromatic hydrocarbons (e.g., paraffins, alkylbenzenes, alkyl naphtha benzenes, chlorobenzenes), alcohols and polyols (which, where appropriate, In this case, it may be substituted, etherified and / or esterified. ketones (e.g., acetone, cyclohexanone), esters (which includes fats and oils) and (poly)ethers, simple amines and and substituted amines, amides, lactams (e.g., N-alkylpyrrolidone ), and lactones, sulfones and sulfoxides (e.g., dimethyl sulfonates, oxides), carbonates and nitriles.

[0219] When the extender used is water, an organic solvent, for example, can also be used as a co-solvent. Useful liquid solvents are essentially the following: aromatic compounds, e.g., xylene; Toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons chlorine, for example, chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons cyclohexane or paraffins, such as petroleum fractions, mineral oils and vegetable oils Oils, alcohols, e.g. butanol or glycols and their ethers and esters esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl Sulfoxides, carbonates, such as propylene carbonate, butylene carbonate, and diethyl carbonate or dibutyl carbonate, or nitriles such as acetonitrile or propane Nitrile.

[0220] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic carbons; Hydrogen chlorine or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or salts methylene chloride, aliphatic hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral oil and vegetable oils, alcohols, e.g., methanol, ethanol, isopropanol, ethanol or glycols and their ethers and esters, ketones, e.g., acetones, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvent solvents such as dimethyl sulfoxide, carbonates such as propylene carbonate, ethylene, diethyl carbonate or dibutyl carbonate, nitriles such as acetonitrile or The solvents are propanenitrile and water.

[0221] In principle, all suitable carriers can be used. Useful carriers include, in particular, Examples of suitable ammonium salts include ammonium salts and finely divided ammonium salts. Natural rocks, such as kaolin, alumina, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth, and finely ground synthetic rocks, e.g., highly dispersed silica moss, aluminum oxide, and natural or synthetic silicates, resins, waxes, and and / or solid fertilizers. Mixtures of such carriers can be used as well. Useful carriers for this purpose include, for example, crushed and fractionated Natural rocks, such as calcite, marble, pumice, sepiolite, dolomite, and inorganic and organic and synthetic granules consisting of powders of organic materials (e.g. sawdust, paper, coconut). Granules made from grains such as corn husks, corn cobs, and tobacco petioles.

[0222] It is also possible to use liquefied gas extenders or solvents. Particularly suitable extenders or The carrier is an extender or carrier that is a gas at standard temperature and atmospheric pressure, e.g., an aerosol. propellants, such as halogenated hydrocarbons, and also butane, propane, nitrogen and and carbon dioxide.

[0223] Emulsifiers and / or foam formers, dispersants with ionic or non-ionic properties Examples of wetting agents or mixtures of these surface-active substances are salts of polyacrylic acid. , salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, Polycondensation of ethylene oxide and fatty alcohol or polycondensation of ethylene oxide and fatty acid or polycondensation products of ethylene oxide and fatty amines, substituted with ethylene oxide a polycondensate of a phenol (preferably an alkylphenol or an arylphenol) , a salt of sulfosuccinate, a taurine derivative (preferably an alkyl taurate), Isethionate derivatives, phosphate esters of polyethoxylated alcohols or polyethoxylated Phosphate esters of hydroxylated phenols, fatty acid esters of polyols, as well as sulfates and sulfuric acid salts. Derivatives of the compounds containing benzoates and phosphates, e.g., alkylarylpolybenzoates, Glycol ethers, alkyl sulfonates, alkyl sulfates, aryls sulfonates, protein hydrolysates, lignosulfite waste liquor, and methylcellulose The compound of formula (I) and / or the inert carrier If one of them is water-insoluble and application is with water, a surfactant may be present. It is advantageous to

[0224] Further adjuvants which may be present in the formulation and in the use forms derived therefrom include: colorants, such as inorganic pigments, for example, iron oxide, titanium oxide, and Prussian blue (Prussian Blue), as well as organic dyes such as alizarin dyes and azo dyes. pigments and metal phthalocyanine dyes, as well as nutrients and micronutrients, such as iron salts, maize Examples include magnesium salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.

[0225] Further ingredients that may be present include stabilizers (e.g., low-temperature stabilizers), preservatives, antioxidants, A light stabilizer or other agent that improves chemical and / or physical stability. Additionally, foam-producing or anti-foaming agents may also be present.

[0226] Furthermore, the preparation and the use forms derived therefrom may contain, as additional adjuvants, and adhesives such as carboxymethylcellulose, and powders or granules or Natural and synthetic polymers in the form of latex, e.g., gum arabic, poly Vinyl alcohol and polyvinyl acetate, or natural phospholipids, such as cephalin and Further adjuvants may include lecithin, synthetic phospholipids, etc. , mineral oil and vegetable oil.

[0227] Where appropriate, the preparation and the use forms derived therefrom may contain further supporting ingredients. Examples of such additives are fragrances, protective colloids, binding agents, agents, adhesives, thickeners, thixotropic agents, penetrating agents, retention promoters, stabilizers, sequestering agents, complexing agents Generally, the compounds of formula (I) are used for formulation purposes. It can be combined with any commonly used solid or liquid additive.

[0228] Useful retention aids include any material that reduces dynamic surface tension, e.g., sulfosuccinate. dioctyl acetate or any substance that increases viscoelasticity, such as hydroxypropyl guar Polymers are included.

[0229] Penetrants useful in connection with the present invention are compounds that enhance the penetration of pesticidal active compounds into plants. In this context, penetrants are all substances that are typically used for Generally, from the application liquid (aqueous) and / or from the spray coating on the plant cuticle. and thereby enhance the mobility of the active compound within the cuticle. The ability of the bacteria to cause disease is defined by the following criteria (see Baur et al., 1997, Pesticide Science The method described in (inc. 51, 131-152) was used to confirm this property. Examples include alcohol alkoxylates, e.g., coconut Fatty ethoxylate (coconut fatty ethoxylate) (10) or isotridecyl ethoxylate (12), fatty acid esters, e.g., rapeseed oil methyl esters or soybean oil methyl esters, fatty amine alkoxylates, e.g., Fatty amine ethoxylates (15), or ammonium salts and / or phosphonium salts ammonium sulfate or diammonium hydrogen phosphate. can.

[0230] The formulation preferably contains 0.00000001% by weight to 9% by weight based on the weight of the formulation. 8% by weight of the compound of formula (I), more preferably 0.01% by weight % by weight of the compound of formula (I), and most preferably 0.5% by weight It contains up to 90% by weight of the compound represented by formula (I).

[0231] The compound represented by formula (I) in the use form prepared from the formulation (especially a pesticide) The content of the compound of formula (I) in the formulation can vary within a wide range. The concentration of the compound is generally 0.00000001% by weight based on the weight of its use form. up to 95% by weight of the compound represented by formula (I), preferably 0.00001% by weight to 1% by weight % of the compound of formula (I). The compound is prepared by a conventional method suitable for the form of use. Used.

[0232] mixture The compounds of formula (I) may be used, for example, to extend the spectrum of action by increasing the duration of action. To prolong the life of the product, to increase the speed of action, to prevent repellency, or to One or more suitable fungicides, bactericides, acaricides, and molluscs to prevent resistance development. Animal repellents, nematicides, insecticides, microbiological agents t), beneficial organisms, herbicides, fertilizers, bird repellents, plant strengtheners (phytotonic), sterilization in mixtures with pesticides, safeners, semiochemicals and / or plant growth regulators. Furthermore, active compound combinations of this type can improve plant growth. and / or abiotic factors, e.g., tolerance to high or low temperatures, drought Improving water resistance or tolerance to increased water content or soil salinity Furthermore, it is possible to improve flowering and fruiting performance, and It is also possible to optimize the plant's capacity and root development and to facilitate harvesting. It is possible to improve yield, influence maturity, and reduce harvest time. It is also possible to improve the quality and / or nutritional value of harvested produce. It is also possible to increase the shelf life of the produce and / or improve the processing of the harvested produce. It is also possible to improve the performance.

[0233] Furthermore, the compounds of formula (I) may be combined with another active compound or semiochemical, e.g. attractants, and / or bird repellents, and / or plant activators, and / or It may also be present in a mixture with growth regulators and / or fertilizers. The compounds of formula (I) are useful for improving plant characteristics, such as growth, yield and quality of the harvested product. It can also be used to raise

[0234] In a particular embodiment according to the invention, the compound of formula (I) is present in the formulation or In the use forms prepared from such formulations, further compounds, preferably It is present in admixture with the compounds described.

[0235] When one of the compounds described below can exist in various tautomeric forms , and in each case, even if not explicitly mentioned, these forms are equally included. All mixture components described are based on their functional groups, where possible. In some cases, salts can also be formed with suitable bases or acids.

[0236] Insecticides / Acaricides / Nematicides The active compounds identified herein by "common name" are known and For example, see "The Pesticide Manual", 16th ed., B Listed in the British Crop Protection Council 2012 or can be found on the internet (e.g. http: / / www.alanwood.net / pesticides). The classification is The IRAC Mode of Action Class applicable at the time of filing of the application It is based on the sification scheme.

[0237] (1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates This series includes alanycarb, aldicarb, bendiocarb, benfuracarb, butocarb butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethoxycarbazole Ofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, Methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, Odicarb, thiofanox, triazamate, trimethacarb, XMC and xyli or organophosphate esters, such as acephate, azaphosphate, Metiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyphos , chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos Dichlorvos / DDVP, Dicrotophos, Dimethicone Methoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, Famful, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Hepta Nofos, Imicyaphos, Isofenphos, O-(methoxyaminothiophosphoryl)salicylic acid Isopropyl phosphate, isoxathion, malathion, mecarbamate, methamidophos, methidazole On, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, Parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamide phenanthrene, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, Pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, teme phos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion.

[0238] (2) GABA-regulated chloride channel blockers, preferably cyclodiene-organochlorines systems, which are selected from chlordane and endosulfan; or phenylpyra azoles (fiproles), which are selected from ethiprole and fipronil; .

[0239] (3) sodium channel modulators, preferably pyrethroids, which are , acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin Bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, Bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin Phosphorus, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin Lumethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [ (EZ)-(1R) isomer], esfenvalerate, etofenprox, fenp Lopatrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate Halfenprox, Imiprothrin, Kadetrin, Momfluorotrin, Perme thrin, fenothrin [(1R)-trans isomer], prallethrin, pyrethrins (excluding Pyrethrum, resmethrin, silafluofen, tefluthrin, tet Lametrin, tetramethrin [(1R) isomer], tralomethrin and transflut or DDT; or methoxychlor.

[0240] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, preferably Or neonicotinoids, which include acetamiprid, clothianidin, and dinotefuran. , imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine; or sulfoximines selected from sulfoxaflor, or or a butenolide selected from flupyradifurone, or triflumezopyrim Selected mesoionic compounds.

[0241] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators -, preferably a spinosyn selected from spinetoram and spinosad.

[0242] (6) Allosteric modulation of glutamate-regulated chloride channels (GluCl) ter, preferably abamectin, emamectin benzoate, lepimectin and milbe Avermectins / milbemycins selected from mectins.

[0243] (7) Juvenile hormone mimetics, preferably hydroprene, kinoprene and methoprene. a juvenile hormone analog selected from the group consisting of phenoxycarb, phenoxycarb, and pyriprazole; Roxifene.

[0244] (8) Various unspecified (multi-site) inhibitors, preferably methyl bromide and other alkyl halides selected from the alkyl halides of the above, or chloropicrin; or sulfuryl fluoride; or borax; or tartar emetic; or dazomet (d a methyl isocyanate generator selected from iazomet and metam;

[0245] (9) Chordotonal organ TRPV channel modulators, including pymetrozine and pyrifluquinazone.

[0246] (10) Mite growth inhibitors, such as clofentezine, hexythiazox, and diflovir. It is selected from Dazin and Etoxazole.

[0247] (11) A microbial disruptor of the insect gut membrane, Bacillus thuringiensis Subspecies israelensis (Bacillus thuringiensis subs pecies israelensis, Bacillus sphaericus s sphaericus), Bacillus thuringiensis subsp. aizawai (Bac illus thuringiensis subspecies aizawa), Bacillus thuringiensis subspecies kurstaki (Bacillus thuringi ensis subspecies kurstaki), Bacillus thuringiensis Subspecies tenebrionis (Bacillus thuringiensis subsp ecies tenebrionis), and Bt plant proteins (which Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, Select from mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1 (selected from the list).

[0248] (12) Mitochondrial ATP synthase inhibitors, preferably diafenthiuro ATP disruptors selected from azocyclotin, cyhexatin and an organotin compound selected from fenbutatin oxide or propargite; or Tetrazifon.

[0249] (13) Uncouplers of oxidative phosphorylation by disrupting the proton gradient, which It is selected from lorfenapir, DNOC and sulfluramide.

[0250] (14) Nicotinic acetylcholine receptor channel blockers, which include bensultat selected from thiosultap, cartap hydrochloride, thiocyclam and thiosultap-sodium .

[0251] (15) Chitin biosynthesis inhibitors (type 0), such as bistrifluron and chlorflurane. Luazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflu Muron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflu Selected from Muron.

[0252] (16) Chitin biosynthesis inhibitors (type 1), which are selected from buprofezin do.

[0253] (17) Molting disruptors (especially in Diptera), which are selected from Cyromagines will be done.

[0254] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, and metoprolol. It is selected from toxifenozide and tebufenozide.

[0255] (19) Octopamine receptor agonists, which are selected from amitraz.

[0256] (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon, Selected from acequinocyl and fluacrypyrim.

[0257] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides; These include fenazaquin, fenpyroximate, pyrimidifen, pyridaben, and tebufenox. or rotenone (Derris).

[0258] (22) Voltage-dependent sodium channel blockers, such as indoxacarb and metaflumizone.

[0259] (23) Acetyl-CoA carboxylase inhibitors, preferably tetronic acid derivatives and tetramic acid derivatives, such as spirodiclofen fen), spirodiclofen, spiromesifen and spirotetramat do.

[0260] (24) Mitochondrial complex IV electron transport inhibitors, preferably phosphine-based, It is selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide. or cyanides, which include calcium cyanide, potassium cyanide and cyanide; sodium fluoride.

[0261] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitriles derivatives, which are selected from cyenopyrafen and cyflumetofen; or The ruboxianilides are selected from piflubumid.

[0262] (28) Ryanodine receptor modulators, preferably diamides, which are Selected from lantraniliprole, cyantraniliprole and flubendiamide .

[0263] (29) Modulators of chordotonal organs (target structures not defined), which The compound is selected from the group consisting of nicamides.

[0264] (30) An additional active compound selected from the following: acinonapyr, afidopyr Ropen, Afoxolaner, Azadirachtin, Benclotiaz, Benzoximate, Be Nzpirimoxan, bifenazate, broflanilide, bromopropylate, chinomethionine nate, chlorprallethrin, cryolite, cyclaniliprole, cyclamate cycloxaprid, cyhalodiamid e), dichloromezothiaz, dicofol, ε-metofluthrin, ε-momfluorothrin ( epsilon momfluthrin), flometoquin, fluazaindolizine, Luensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Flu Hexafon, fluopyram, flupirimine, fluralaner, fluxametamide, fufeno Fufenozide, guadipyr, heptafluthrin, imidacloprid, ip Rhodion, κ-bifenthrin, isocycloseram, κ -Tefluthrin, Lotilaner, Meperfluthrin, Oxazosulfur Phil, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spi spirobudiclofen, spiropidione, tetramethyl Fluthrin, tetraniliprole, tetrachlorantraniliprole (tetrachl orantraniliprole, tigolaner, thioxaza Phen, thiofluoximate and iodomethane; Furthermore, a preparation based on Bacillus firmus (I -1582, BioNeem, Votivo), and the following compound: 1-{2-fluro[pi]pyrrolidone Oro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl }-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (WO Known from 2006 / 043635) (CAS 885026-50-6), {1'-[( 2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[pi] 1(2H)-chloropyridine-3,4'-dichloro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridine- 4-yl)methanone (known from WO2003 / 106457) (CAS 637360- 23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)propane 4-(trifluoromethyl)phenyl nyl]isonicotinamide (known from WO2006 / 003494) (CAS 8729 99-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy- 8-Methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (WO201 0052161) (CAS 1225292-17-0), 3-(4-chloro- 2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4. 5] Dec-3-en-4-yl ethyl carbonate (known from EP 2647626) ( CAS-1440516-42-6), 4-(but-2-yn-1-yloxy)-6- (3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (WO2004 / 099160) (CAS 792914-58-0), PF1364 (JP20 Known from 10 / 018586) (CASReg.No.1204776-60-2), ( 3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1 , 1,1-trifluoropropan-2-one (known from WO2013 / 144213) ( CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chloro [1-methyl-3-(pentafluoroethyl)-4-(trifluoromethylphenyl)]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl )-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) ( CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2 -methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl) Pyrazole-3-carboxamide (known from CN103232431) (CAS 144 9220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro- 5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1- Oxido-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)- 4,5-Dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl -N-(trans-1-oxido-3-thietanyl)benzamide and 4-[(5S) -5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl) -3-Isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl) Benzamide (known from WO2013 / 050317A1) (CAS 1332628- 83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl ]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propane Amide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4- -N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionate Panamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazoline -4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl propanamide (WO2013 / 162715A2, WO2013 / 162716A 2, known from US2014 / 0213448A1) (CAS 1477923-37-7 ), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6 -dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)s [Sulfinyl]-1H-pyrazole-3-carbonitrile (from CN101337937A Known) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl thyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-phenyl) Lysinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxu anan, known from CN103109816A) (CAS 1232543-85-9) ;N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6- Methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)- 1H-pyrazole-5-carboxamide (known from WO2012 / 034403A1) CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazonium]

[00100] -3-bromo-1-(3-chloro-2-yl)-4-chloro-6-methylphenyl (2-pyridinyl)-1H-pyrazole-5-carboxamide (WO2011 / 085 575A1) (CAS 1233882-22-8), 4-[3-[2,6-di Chloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]prop [C]-2-methoxy-6-(trifluoromethyl)pyrimidine (CN101337 940A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[ 2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene ]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (CN10 Known from 1715774A) (CAS 1232543-85-9); cyclopropane 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzyl)carboxylic acid midazol-2-yl)phenyl ester (known from CN103524422A) (CA S 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[ [(Methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino] [carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carbohydrate Methyl carboxylic acid ester (known from CN102391261A) (CAS 1370358 -69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[ 4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H- 1,2,4-Triazol-3-yl]phenyl]carbamate]-α-L-mannopyramide North (known from US2014 / 0275503A1) (CAS 1181213-14 -8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3 -(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1] Octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropyl) (4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyrrolidone Ridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 93379 8-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoro Methylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-aza Bicyclo[3.2.1]octane (WO2007040280A1, WO2007040 282A1) (CAS 934001-66-8), N-[3-chloro-1-( 3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- trifluoropropyl)thio]propanamide (WO2015 / 058021A1, WO Known from 2015 / 058028A1) (CAS 1477919-27-9) and N -[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl] Phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5 -carboxamide (known from CN103265527A) (CAS 1452877-5 0-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl )phenyl]methoxy]pyrimidine (known from WO2013 / 115391A1) (CA S 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-8 -Methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (W Known from O2014 / 187846A1) (CAS 1638765-58-8), 3- (4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo- Ethyl 1,8-diazaspiro[4.5]dec-3-en-4-ylcarboxylate (WO2 010 / 066780A1, WO2011151146A1) (CAS 122 9023-00-0), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl -4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[ (4R)-2-Ethyl-3-oxo-4-isoxazolidinyl]-2-methylbenzal mide (known from WO2011 / 067272 and WO2013 / 050302) (CAS 1309959-62-3).

[0265] disinfectant The active compounds identified herein by "common name" are known and For example, see the "Pesticide Manual" (16th Ed., British listed on the Crop Protection Council, or , can be searched on the Internet (e.g.: http: / / www.ala nwood.net / pesticides ").

[0266] All mixture components listed in classes (1) to (15) are classified based on their functional groups. If possible, salts can be formed with suitable bases or acids. All fungicide mixture components described in (1) to (15) may, in some cases, exist in tautomeric forms. It may include the following states.

[0267] 1) Ergosterol biosynthesis inhibitors, for example, (1.001) cyproconazole, ( 1.002) Difenoconazole, (1.003) Epoxiconazole, (1.004) Fenhexamid, (1.005) fenpropidin, (1.006) fenpropimol F, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.00 9) Flutriafol, (1.010) Imazalil, (1.011) Imazalil sulfate, ( 1.012) Ipconazole, (1.013) Metconazole, (1.014) Microb Tanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.01 7) Propiconazole, (1.018) Prothioconazole, (1.019) Pyrisoxazole azole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022 ) Tetraconazole, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorophenyl) 1H-1,2,4-trichlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-trichlorobenzyl)- (1S,2R,5R)-cyclopentanol, (1.027)(1S,2R,5R)- 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2 ,4-triazol-1-ylmethyl)cyclopentanol, (1.028)(2R)- 2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl ]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (1.0 29) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichloro Isocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butane-2- ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)-2-propanol] [1H-1,2,4-triazol-1-yl]propanol cyclopropyl-2-ol, (1.031)(2S)-2-(1-chlorocyclopropyl)-4-[ (1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazole -1-yl)butan-2-ol, (1.032)(2S)-2-(1-chlorocyclopropanediol), propyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2, 4-triazol-1-yl)butan-2-ol, (1.033)(2S)-2-[4 -(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1 ,2,4-triazol-1-yl)propan-2-ol, (1.034)(R)-[ 3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-pyridin ,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035)( S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl [0.01]-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.0 36) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl) [0.01]-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.0 37) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenoxy] Nyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4- Triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4- chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl )-1H-1,2,4-triazole, (1.039)1-{[3-(2-chlorophenyl (2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1 ,2,4-triazol-5-yl thiocyanate, (1.040)1-{[rel(2 R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxy lan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate , (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-( 2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-trifluorophenyl Triazol-5-yl thiocyanate, (1.042)2-[(2R,4R,5R)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane- 4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1. 043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydro [2,4-dihydro-3H-1,2-xy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro- ,4-triazole-3-thione, (1.044)2-[(2R,4S,5R)-1-( 2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane-4- yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.04 5) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy -2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4 -triazole-3-thione, (1.046)2-[(2S,4R,5R)-1-(2, 4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl ]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2 ,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-trimethylheptan-4-yl Riazole-3-thione, (1.048)2-[(2S,4S,5R)-1-(2,4- Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-Dihydro-3H-1,2,4-triazole-3-thione, (1.049)2- [(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6 ,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-trimethylheptan-4-yl 2-[1-(2,4-dichlorophenyl)-5-hydroxybenzoyl]-3-thione, (1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxybenzoyl]-3-thione Hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1 ,2,4-triazole-3-thione, (1.051)2-[2-chloro-4-(2,4 -dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl ) propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy) [1H-phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl) phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenoxy] nyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, ( 1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl] [1H-1,2,4-triazol-1-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, .056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl) Oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole -3-thione, (1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl -2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4- Dihydro-3H-1,2,4-triazole-3-thione, (1.058)2-{[re l(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) Oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole -3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2 -methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanoate (1.060) 5-(arylsulfanyl)-1-{[3-(2-chlorophenyl) -2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2 ,4-triazole, (1.061)5-(arylsulfanyl)-1-{[rel(2 R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxy lan-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(azoline (2R,3S)-3-(2-chlorophenyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2 -(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4 -triazole, (1.063)N'-(2,5-dimethyl-4-{[3-(1,1,2 ,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N -Methylimidoformamide, (1.064)N'-(2,5-dimethyl-4-{[3- (2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethoxy N-methylimidoformamide, (1.065)N'-(2,5-dimethyl-4-{ [3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl (1.066)N'-(2,5-diphenyl)-N-ethyl-N-methylimidoformamide Methyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl) -N-ethyl-N-methylimidoformamide, (1.067)N'-(2,5-dimethyl 4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy }phenyl)-N-ethyl-N-methylimidoformamide, (1.068)N'-(2 ,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl (1.069)N'-( ... -(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfonyl (phenyl)phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1 .070)N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfa N-ethyl-N-methylimidoformamide, (1.0 71) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl Imidoformamide, (1.072)N'-(4-{[3-(difluoromethoxy)phenyl N-ethyl-N-methylimidophenyl)-2,5-dimethylphenyl Fluoromethylsulfanamide, (1.073)N'-(4-{3-[(difluoromethyl)sulfanyl] {phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide (1.074)N'-[5-bromo-6-(2,3-dihydro-1H-indene-2 -yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidophor amide, (1.075)N'-{4-[(4,5-dichloro-1,3-thiazole-2 -yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoform Amide, (1.076)N'-{5-bromo-6-[(1R)-1-(3,5-difluoromethyl)amino] (triphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylisothiazolinone Iodoformamide, (1.077)N'-{5-bromo-6-[(1S)-1-(3,5 -difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N -Methylimidoformamide, (1.078)N'-{5-bromo-6-[(cis-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl -N-methylimidoformamide, (1.079)N'-{5-bromo-6-[(tran (4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N -ethyl-N-methylimidoformamide, (1.080)N'-{5-bromo-6-[ 1 -(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N- Ethyl-N-methylimidoformamide, (1.081) Ipfentrifluconazole .

[0268] 2) Inhibitors of the respiratory chain at complex I or complex II, e.g., (2.001)beta Nzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2. 004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, ( 2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isoflurane etamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S ,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R ,9R), (2.012) isopyrazam (anti-epimer racemic compound 1RS,4S R,9SR), (2.013) isopyrazam (syn-epimer racemic compound (1RS, A mixture of the anti-epimer racemic compound (1RS,4SR,9SR) and the anti-epimer racemic compound (1RS,4SR,9SR) substance), (2.014) Isopyrazam (syn-epimer enantiomers 1R,4S,9R ), (2.015) Isopyrazam (syn-epimer enantiomer 1S,4R,9S) , (2.016) Isopyrazam (syn-epimer racemic compounds 1RS, 4SR, 9RS ), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pi Diflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2. 022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H- Inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3 -dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-yne 1,3-di-(2,024)-1H-pyrazole-4-carboxamide Methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene -4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3 -(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl ]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl) Fluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene -4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N -(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H- Pyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-1-methyl N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4 -yl]-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)- (3S)-1,1,3-trimethyl-2,3-dihydro-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030)3 -(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro- 1H-inden-4-yl-1-methyl-1H-pyrazole-4-carboxamide (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1 ,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H -pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[ (3S)-7-Fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene -4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033)5 ,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pi Lysin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034 )N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(di Fluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide , (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl Pyr-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4- Carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropanol Hydroxypropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4 -carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclohexyl 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole -4-Carboxamide, (2.038) N-(5-chloro-2-isopropylbenzyl) -N-Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H- Pyrazole-4-carboxamide, (2.039)N-[(1R,4S)-9-(dichloro) (methylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, ( 2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrachloromethane [0.001]-3-(difluoromethyl)-1-methyl-1,4-naphthalen-5-yl thyl-1H-pyrazole-4-carboxamide, (2.041)N-[1-(2,4-di chlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1 -Methyl-1H-pyrazole-4-carboxamide, (2.042)N-[2-chloro- 6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl )-5-Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043 )N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclohexyl 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole -4-carboxamide, (2.044)N-[5-chloro-2-(trifluoromethyl) benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl N-cyclopropyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3- (Difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)methyl] (2.046)N- Cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6- isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2. 047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl) (isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N -(2-Isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamine N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N -(2-Isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide , (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N- (5-Fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxylate Ruboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-( 2-Ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazoline N-cyclopropyl-3-(difluoromethyl)-4-carboxamide, (2.052) )-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pi 4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl) Methyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H -pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl) Chloropropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1 -Methyl-1H-pyrazole-4-carboxamide, (2.055)N-cyclopropyl -N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5- Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056)N- Chloropropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5- Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) Pyrap pyrapropoyne.

[0269] 3) Inhibitors of the respiratory chain at complex III, for example (3.001) amethoctradi , (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.004 ) Coumethoxystrobin, (3.005) Spider Xystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadone, (3.010) F Flufenamidon, (3.011) Flufenoxystrobin bin), (3.012) Fluoxastrobin, (3.013) Kresoxim-methyl , (3.014) metominostrobin, (3.015) orysastrobin, (3.016 ) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametos strobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin N, (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1 -fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl {ethyl}phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl] oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3. 023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}- 2-Methoxy-N-methylacetamide, (3.024)(2S)-2-{2-[(2, 5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide , (3.025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(iso butyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanol Nonoate, (3.026) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl {2-methoxy-N-methylacetamide}, (3.027) N-(3-ethyl-3, 5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide , (3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl) -1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethyl Pent-3-enamide, (3.029){5-[3-(2,4-dimethylphenyl)- 1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.03 0) Methyltetraprole, (3.031) Florylpicoxamide.

[0270] 4) Mitosis and cell division inhibitors, for example, (4.001) carbendazim, ( 4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluo Picolide, (4.005) Pencycuron, (4.006) Thiabendazole, (4.00 7) Thiophanate-methyl, (4.008) Zoxamide, (4.009) 3-chloro- 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.0 10) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridine-3- yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.0 12) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl) )-1,3-dimethyl-1H-pyrazol-5-amine, (4.013)4-(2-bromo (2-bromo-6-fluorophenyl)-N-(2-bromo-4-fluorophenyl)-1,3-di Methyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluoro (2-bromophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5 -amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro (4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, .016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)- 1,3-Dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo- (4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pi 4-(2-chloro-4-fluorophenyl)-N-thiazol-5-amine, (4.018) -(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine , (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6- Fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020 )4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3- Dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluoro (2-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole -5-Amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluoro phenyl)-3,6-dimethylpyridazine, (4.023)N-(2-bromo-6-fluoro (2-chloro-4-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H -pyrazol-5-amine, (4.024)N-(2-bromophenyl)-4-(2-chlorophenyl)- (4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4 -fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

[0271] 5) Compounds capable of exhibiting multi-site activity, e.g., (5.01) Bordeaux mixture, (5.02) ) Captafol, (5.03) Captan, (5.04) Chlorothalonil, (5.05) Copper hydroxide, (5.06) copper naphthenate, (5.07) copper oxide, (5.08) copper oxychloride , (5.09) Copper(2+) sulfate, (5.10) Dithianon, (5.011) Dodine, (5 .012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.01 5) Metiram, (5.016) Metiram zinc, (5.01 7) Oxine-copper, (5.018) Propineb, (5.01 9) Sulfur and sulfur agents, for example, calcium polysulfide, (5.020) thiuram, (5.0 21) Zineb, (5.022) Ziram, (5.023) 6-ethyl-5,7-dioxo- 6,7-Dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3- c][1,2]Thiazole-3-carbonitrile.

[0272] 6) Compounds capable of inducing host defenses, such as (6.001) acibenzolar-S- Methyl, (6.002) Isotianil, (6.003) Probenazole, (6.004) Tiadinil.

[0273] 7) Inhibitors of amino acid and / or protein biosynthesis, e.g. (7.001) Cyprodinil, (7.002) Kasugamycin, (7.003) Kasugamycin Hydrochloride Aqueous Solvate, (7.004) Oxytetracycline, (7.005) Pyrimethanil, (7.0 06) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline (lin-1-yl)quinoline.

[0274] 8) ATP production inhibitors, for example, (8.001) silthiofam.

[0275] 9) Cell wall synthesis inhibitors, for example, (9.001) benthiavalicarb, (9.002 ) Benthiavalicarb-isopropyl, (9.003) Dimethomorph, (9.004) F Lumorph, (9.005) iprovalicarb, (9.006) mandipropamide, (9. 007) Pyrimorph, (9.008) Valifenalate, (9.009) (2E)-3- (4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(molybdenum)- (4-fluorolin-4-yl)prop-2-en-1-one, (9.010)(2Z)-3-(4 -tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpho (lin-4-yl)prop-2-en-1-one.

[0276] 10) Inhibitors of lipid and membrane synthesis, for example, (10.001) propamocarb, ( 10.002) Propamocarb hydrochloride, (10.003) Tolclofos-methyl.

[0277] 11) Melanin biosynthesis inhibitors, for example, (11.001) tricyclazole, (11 .002)2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl) 1-(2-amino)butan-2-yl}carbamate.

[0278] 12) Nucleic acid synthesis inhibitors, for example, (12.001) benalaxyl, (12.002) Benalaxyl-M (chiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (mefenoxam).

[0279] 13) Signal transduction inhibitors, for example, (13.001) fludioxonil, (13. 002) Iprodione, (13.003) Procymidone, (13.004) Proquinazide , (13.005) quinoxyfen, (13.006) vinclozolin.

[0280] 14) Compounds that can act as uncouplers, for example (14.001) fluazinam, (14.002) Meptylzinocup.

[0281] 15) Further compounds, such as (15.001) abscisic acid, (15.002) Benthazole, (15.003) bethoxadin, (15.004) capsimycin (c apsimycin), (15.005) carvone, (15.006) chinomethionate , (15.007) Kufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) Fosetyl-aluminum, (15.013) Fosetyl-calcium, ( 15.014) Fosetyl sodium, (15.015) Methyl isothiocyanate, (1 5.016) Metrafenone, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.020 ) Nitrothal-isopropyl, (15.021) Oxamocarb , (15.022) oxathiapiproline, (15.023) oxyfenthiin (ox yfenthiine), (15.024) Pentachlorophenol and salts, (15. 025) Phosphonic acids and their salts, (15.026) Propamocarb-fosetylate (p ropamocarb-fosetylate), (15.027) pyriophenone ( Lazafenone, (15.028) Tebufloquine, (15 .029) Tecloftalam, (15.030) Tornifanide, (15.031) 1-( 4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1, 2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl )-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]e Tanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl) Nyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazole- 2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)- 1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridine -2-yl)quinazoline, (15.034) 2,6-dimethyl-1H,5H-[1,4] Dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrahydrofuran Thoron, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazole -1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy) [phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazole -2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis( Difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloromethyl 4,5-dihydro-1,4-dichloro-6-(prop-2-yn-1-yloxy)phenyl]- 2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl ]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazoline 2-fluoro-6-(prop-2-yl)-1-[4-(4-{5-[2-fluoro-6-(prop-2-yl)- 1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}- 1,3-Thiazol-2-yl)piperidin-1-yl]ethanone, (15.038)2 -[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl] Nazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(diphenyl (fluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl} -3-Chlorophenyl methanesulfonate, (15.040)2-{(5S)-3-[ 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetate thiazole-4-yl)-4,5-dihydro- 1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15 .041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy ]-6-fluorophenyl}propan-2-ol, (15.042) 2-{2-fluoro 6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propanol 2-(3-[2-(1-{[3,5-bis(difluoromethyl) (trimethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3 -thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3 -Chlorophenyl methanesulfonate, (15.044)2-{3-[2-(1-{[ 3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidinyl

[00100] -1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxa {5-(2-phenyl-5-yl)phenyl methanesulfonate, (15.045) 2-phenylphenyl and its salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl (15.047)3-(4-(4-methyl-3,4-dihydroisoquinolin-1-yl)quinoline ,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quino Phosphorus, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form Form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4- Oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050) 5-amino-1 ,3,4-Thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl N'-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide, (1 5.052) 5-Fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4- Amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine Zin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinoline) -3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) porcine -3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazole-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbame (15.056) (2Z)-3-amino-2-cyano-3-phenylacrylic acid ester (15.057) Phenazine-1-carboxylic acid, (15.058) 3,4,5-trimethyl- Propyl trihydroxybenzoate, (15.059) Quinolin-8-ol, (15.06 0) Quinolin-8-ol sulfate (2:1), (15.061){6-[({[ (1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy )methyl]pyridin-2-yl}carbamate tert-butyl, (15.062)5- Fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3, 4-Dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen (am inopyrifen).

[0282] Biological pesticides as mixture components The compounds of formula (I) may be combined with a biological pesticide.

[0283] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and microorganisms. These include products formed by the organism (e.g., proteins and secondary metabolites).

[0284] Biological pesticides include bacteria, e.g., spore-forming bacteria, root-colonizing bacteria, and These include bacteria that produce fungi, and bacteria that act as biological insecticides, fungicides or nematicides. do.

[0285] The above bacteria that are used or can be used as biological pesticides An example of this is: Bacillus amyloliquefaciens iens strain FZB42 (DSM 231179), or Bacillus cereus (Ba Bacillus cereus), especially B. cereus strain CN CM I-1562, or Bacillus firmus ) strain I-1582 (accession number CNCM I-1582), or Bacillus pumilus (Bacillus pumilus), in particular strain GB34 (accession number ATCC 70 0814) and strain QST2808 (accession number NRRL B-30087), or Bacillus subtilis, specifically strain GB03 (recipient) Accession number ATCC SD-1397), or Bacillus subtilis (Bacillu S. subtilis strain QST713 (accession number NRRL B-21661), and Bacillus subtilis strain OST 3000 2 (Accession No. NRRL B-50421), Bacillus thuringiensis (Bacil Bacillus thuringiensis), especially Bacillus thuringiensis subsp. B.thuringiensis subspecies israe lensis) (antigen type H-14) strain AM65-52 (accession number ATCC 1276) ), or Bacillus thuringiensis subspecies Aizawai (B. thuringie nsis subsp. aizawai), in particular, strain ABTS-1857 (SD-137 2), or Bacillus thuringiensis subsp. kurstaki (B. thuringi ensis subsp. kurstaki) strain HD-1, or Bacillus thuringii Tenebrionis (B. thuringiensis subsp.te nebrionis strain NB 176 (SD-5428), Pasteuria penetrans (Pasteuria penetrans), Pasteuria species (Pasteuria spp.) (Rotylenchulus reniformis) formis)-PR3 (accession number ATCC SD-5834), Streptomyces Streptomyces microflavus strain AQ6 121 (= QRD 31.013, NRRL B-50550), Streptomyces Streptomyces galbus strain AQ 6047 (accession number N RRL 30232).

[0286] Fungi and fungi that are used or can be used as biological pesticides Examples of yeasts are: Beauveria bassiana, specifically strain ATCC 74040, Coniothyrium minitans (Coniothyrium minita ns), in particular, strain CON / M / 91-8 (accession number DSM-9660), Lecanisiriu Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Known as Verticillium lecanii In particular, strain KV01, Metarhizium anisopliae (Metarhizium anisopliae), in particular strain F52 (DSM3884 / ATCC 90448) , Metschnikowia fructico la), in particular, strain NRRL Y-30752, Paecilomyces fumosoroseus (Pae cilomyces fumosoroseus) (New: Isaria fumosorosea (I saria fumosorosea), in particular strain IFPC 200613 or strain A popka 97 (accession number ATCC 20874), Paecilomyces lilacinus ( Paecilomyces lilacinus), especially Paecilomyces lilacinus ( P. lilacinus ) strain 251 (AGAL 89 / 030550), Talaromyces Talaromyces flavus, especially strain V117b, Trichoderma Trichoderma atroviride, especially strain SC 1 (Accession number CBS 122089), Trichoderma harzianum (Trichod erma harzianum), especially Trichoderma harzianum riffai (T. harzianum rifai)T39 (accession number CNCM I-952).

[0287] Viruses that are used or can be used as biological pesticides An example of this is: Smaller apple tortrix (Adoxophyes orana) granulosis virus (GV) , codling moth (Cydia pomonella) granulosis virus (GV), tobacco Helicoverpa armigera nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) )mNPV, Spodoptera frugiperda (fa armyworm) mNPV, Egyptian armyworm (Spodoptera littoralis) toralis(African cotton leafworm)NPV.

[0288] added as an "inoculum" to plants or plant parts or plant organs, Bacteria and fungi that promote plant growth and plant health through specific properties are also Examples include: Agrobacterium spp., Azorhizobium Azorhizobium caulinodans, Azospirill Azospirillum spp., Azotobacter spp. cter spp.), Bradyrhizobium spp. ), Burkholderia spp., especially Burkholderia Burkholderia cepacia (formerly known as Pseudomonas cepacia) Pseudomonas cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum (Gi gaspora monosporum), Glomus spp., Laccaria spp., Lactobacillus buchneri obacillus buchneri, Paraglomus species spp.), Pisolithus tinctorus , Pseudomonas spp., Rhizobium spp. zobium spp.), especially Rhizobium trifolii (Rhizobium tr ifolii), Rhizopogon spp., Scleroderma Scleroderma spp., Suillus spp. ), Streptomyces spp.

[0289] Plant extracts that are or can be used as biological pesticides and products formed by microorganisms, including proteins and secondary metabolites. Examples of (including) are: Garlic (Allium sativum), Wormwood (Artemisia absinthium) inthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus Celastrus angulatus, American antler plant (C henopodium anthelminticum), chitin, Armour-Ze n, Dryopteris filix-mas, Horsetail (Equi setum arvense), Fortune Aza, Fungastop, Hea ds Up (Quinopodium quinoa saponin extract), insect repellent Chrysanthemum (pyrethrum / pyrethrins), Surinam bittersweet (Quassia amara), Quercus, Quillaja, Rega lia, ("Requiem TM Insecticide), rotenone, riania / Ryanodine, Symphytum officinale, Artemisia (Tanacetum vulgare), Thymol, Triact 70, TriCo n, nasturtium (Tropaeulum majus), nettle (Urtic a dioica), Veratrin, European mistletoe (Viscum album ), Brassicaceae extracts, especially rapeseed powder or mustard powder.

[0290] Safeners as blend components The compounds of formula (I) can be used as safeners, e.g., benoxacor, cloquintocet, (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlor (-ethyl), fenclorim, flurazole, fluxofenim, furilazole , Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Xabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl (phenyl)sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroaza Cetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07- 3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine ( It can be combined with other compounds such as CAS 52836-31-4.

[0291] Plants and plant parts All plants and plant parts can be treated according to the invention. Desirable and undesirable wild or crop plants (naturally occurring crop plants) All plants and plant populations such as cereals (including wheat, rice, rye, wheat, barley, rye, oats), corn, soybeans, potatoes, sorghum I, sugarcane, tomato, pepper, cucumber, melon, carrot, watermelon, onion, Lettuce, spinach, leeks, kidney beans, Brassica plants sica oleracea) (e.g., cabbage) and other vegetable species, cotton, tobacco, rapeseed, and also fruit plants (wherein the fruits are apples, pears, citrus fruits and Crop plants are understood to mean those that have been cultivated using conventional breeding and optimization methods. It may be a plant that can be obtained by biotechnological methods and genetic engineering. The plant may be obtainable by a method or by a combination of said methods. Such crop plants can include transgenic plants. It also includes plant varieties or other protected species that may be protected by plant breeders' rights. Plants include all stages of development, such as seeds, seedlings, and young plants. It should be understood to mean plants (immature plants) through to mature plants. Plant parts include all above-ground and below-ground parts of a plant, such as shoots, leaves, flowers and roots. and organs, examples of which may be mentioned are leaves, needles, stems, trunks, These include flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes. Plants that have been planted or harvested, as well as vegetative propagation propagation material and reproductive organs propagation material, e.g., cuttings, Plant parts also include tubers, rhizomes, slips and seeds.

[0292] The treatment according to the invention of plants and plant parts with compounds of formula (I) can be carried out in a conventional manner. By practical treatment methods, such as immersion, spraying, vaporization, fogging, scattering, etc. The compounds may be applied directly to plants and plant parts by application, painting, injection, etc., or by injecting the compounds into the plants and plant parts. In the case of reproductive organs, In particular in the case of seeds, this can also be achieved by applying one or more coatings.

[0293] As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or hybrids or Plant species and plants obtained by conventional biological breeding methods such as protoplast fusion In yet another preferred embodiment, the product varieties and parts thereof are treated. Transgenics obtained by genetic engineering methods, sometimes in combination with conventional methods. Plants and plant cultivars (genetically modified organisms) and their parts are processed. "Parts of plants" or "Plant The "plant parts" have already been explained above. , particularly preferably commercially available conventional plant varieties or conventional varieties in use, Plants of a plant variety are treated. Plant varieties are those that have been bred by conventional breeding or by mutagenesis or recombinant DNA technology. Means plants with new properties ("traits") obtained through recombinant DNA technology They can be cultivars, varieties, biotypes or genotypes.

[0294] Transgenic plants, seed treatments, and integration events events) Receiving genetic material through genetic modification that confers particularly advantageous and beneficial characteristics ("traits") to a plant All plants collected are preferred transgenic plants or plants treated according to the invention. Examples of such traits are plant varieties (obtained by genetic engineering). Improved growth of plants, improved tolerance to high or low temperatures, drought or underwater or soil Improved tolerance to salt levels in the soil, increased flowering ability, improved yield ease, accelerated maturation, increased yield, improved quality and / or quality of harvested produce or increased nutritional value, improved storage performance of harvested products and / or improved Another particularly important example of such a property is the resistance to pests and harmful microorganisms. (e.g. insects, arachnids, nematodes, mites, slugs and snails) Improved resistance of plants to, for example, toxins formed within the plant, in particular bacillomyces Genes derived from Bacillus thuringiensis Genes [e.g., genes CryIA(a), CryIA(b), CryIA(c), Cr yIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3B b and CryIF and combinations thereof], Pests and harmful microorganisms (e.g. insects, arachnids, nematodes, mites, slugs, etc.) Improved plant resistance to insects (e.g., moths and snails), as well as plant pathogenic fungi, bacteria, and and / or improved resistance of plants to viruses, e.g., systemic acquired resistance (S AR), systemin, phytoalexins, inducers and resistance genes The control of plant pathogenic fungi, bacteria, and Improved resistance of plants to fungi and / or viruses, and also specific herbicidal activity. volatile compounds (e.g., imidazolinones, sulfonylureas, glyphosate or phosphites) Improved plant resistance to steroids (e.g., the "PAT" gene) is desirable. The genes that confer the characteristic ("trait") of interest are recombined with each other in the transgenic plant. Examples of the transgenic plants include Important crop plants, e.g., cereals (wheat, rice, triticale, barley, rye, oat corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other kinds of vegetables, cotton, tobacco, rapeseed, and also fruit plants, where The fruits include apples, pears, citrus fruits, and grapes. Corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco and hatchet The characteristics ("traits") that are particularly important are insects, arachnids, nematodes, and and improved resistance of plants to slugs and snails.

[0295] Crop protection - types of treatment Plants and plant parts may be treated with a compound of formula (I) using conventional methods: For example, immersion, spraying, atomization, irrigation, evaporation, dusting, fogging, scattering, foaming, painting, spreading ( Spreading-on, injection, drenching, drip irrigation, etc. The compounds are applied directly to plants or plant parts by spraying them onto the surrounding area, Treatment is carried out by acting on the breathing environment or storage space, and in the case of reproductive organs, especially In the case of seeds, furthermore, dry seed treatment, liquid seed treatment, and slurry treatment are used to protect the seeds from the coating. In addition, the compound represented by formula (I) may be treated by coating with one or more films. The compounds to be used were sprayed in ultra-low volume. Alternatively, the application form or the compound of formula (I) itself may be applied as a It is also possible to inject it into the soil.

[0296] A preferred direct treatment of plants is foliar application, which is achieved by the addition of a compound of formula (I). In this case, the frequency and amount of application are determined based on the effective amount of the compound. It should be adapted according to the level of pest infestation.

[0297] In the case of systemically active compounds, the compounds of formula (I) can also be transported via the root system. In this case, the plant will reach the plant even if the plant is exposed to the compound of formula (I) in relation to its habitat. This is done by applying a compound that has a specific function, for example, by irrigation. g) or by mixing into the soil or nutrient solution (i.e., in the plant growing area) (e.g., soil or a hydroponic system) with a liquid form of a compound of formula (I). or by soil application [i.e., by applying the compound of formula (I) according to the present invention to a fixed area]. by introducing the plant in a solid form (for example, in granular form) into the plant locus, or by applying drops Subsurface application (often also called "chemigation") that is, soil with varying amounts of water at defined locations within the plant's growing area for a period of time. by introducing the compound of formula (I) via a surface or underground drip line. In the case of rice crops, this can be achieved by administering the compound of formula (I) in solid application form. and by metering the compound (e.g., as a granule) into flooded rice paddies. can be achieved.

[0298] Seed treatment Control of pests by treating plant seeds has been known for a long time and is continually being improved. Nevertheless, seed treatments have not always been satisfactorily resolved. Thus, during storage of the plant, sowing and / or at least significantly reduce the need for additional post-emergence or post-emergence applications of pesticides. It is desirable to develop methods of protecting seeds and germinating plants that will significantly reduce the risk of Furthermore, the active compounds used are effective against pests without causing damage to the plant itself. The active compounds used are selected so that the seeds and germinating plants are optimally protected from attack by It is also desirable to optimize the amount of pesticide used, especially in seed treatment methods. to achieve optimal protection of the seeds and, in addition, of the germinating plants. To achieve this, pest-resistant or pest-tolerant transgenic plants are The intrinsic insecticidal or nematicidal properties of the substance should also be taken into consideration.

[0299] The present invention therefore relates in particular to a method for protecting seeds and germinating plants from attack by pests. The method also relates to a method for cultivating a plant, the method comprising treating the seeds with one of the compounds of formula (I): The present invention provides a method for protecting seeds and germinating plants from attack by pests. The method further comprises treating the seeds with a compound of formula (I) and a mixture of ingredients in one operation. It also includes a method in which the seeds are treated with the methods described above simultaneously or sequentially. The compound of formula (I) and the mixture may be treated at different times. Contains.

[0300] The present invention further provides a method for protecting seeds and the plants produced therefrom against pests. It also relates to the use of compounds of formula (I) for treating seeds.

[0301] The present invention further provides a compound of formula (I) according to the present invention, which is protected against pests. The present invention also relates to seeds treated with the compound. The present invention also relates to seeds treated simultaneously with the synthetic components. The present invention also relates to seeds treated at different times with the compound and mixture components of formula (I). In the case of seeds treated at different times with the compounds and mixture components, the individual substances In this case, the compound of formula (I) and Layers containing mixed components can optionally be separated by intermediate layers. The invention further provides a method for preparing a coating comprising the compound of formula (I) and a mixture thereof, the compound being a part of the coating or a coating. It also relates to seeds that are applied as an additional layer or layers in addition to the membrane. .

[0302] The present invention further provides a method for reducing dust abrasion of seeds after treatment with a compound of formula (I). The present invention also relates to seeds that are subjected to a film coating process to prevent this.

[0303] One advantage of the systemic action of the compounds of formula (I) is that they Treating the seeds not only protects them from pests, but also This means that the plants resulting from the seeds are also protected after emergence. Alternatively, the effort of directly treating the crops shortly after sowing can be avoided.

[0304] A further advantage is that by treating seeds with a compound of formula (I), The result is that the germination and emergence of the seeds can be enhanced.

[0305] The use of the compounds of formula (I) is also particularly relevant to transgenic seeds. It is also considered advantageous that

[0306] Additionally, compounds of formula (I) may be used in combination with signaling technology compositions. It is also possible to identify symbionts (e.g., rhizobia, mycorrhizal fungi and / or endocrine glands) that are responsible for the growth of the plant. colonization by parasitic bacteria or fungi and / or nitrogen Fixation is optimized.

[0307] The compounds of formula (I) can be used in agriculture, in greenhouses, in forestry or in horticulture. It is suitable for protecting the seeds of all plant varieties used in agriculture. In particular, it is suitable for protecting the seeds of cereals (e.g. , wheat, barley, rye, foxtail millet and oats), corn, cotton, soybean, Rice, potato, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g., beets and fodder beets), groundnuts, vegetables (e.g., tomatoes, cucumbers, green beans) seeds of beans, cruciferous vegetables, onions and lettuce), fruit plants, turf and ornamental plants Cereals (e.g., wheat, barley, rye, and oats), corn, Treating the seeds of soybeans, cotton, canola, rapeseed, vegetables and rice is particularly important. be.

[0308] As already mentioned above, transgenic seeds with compounds of formula (I) Of particular importance is the treatment of insecticides, which have, in particular, insecticidal and / or nematicidal properties. A plant generally containing at least one heterologous gene that controls the expression of a polypeptide. These heterologous genes in the transgenic seeds are expressed in Bacillus illus species, Rhizobium species, Pseudomonas monas species, Serratia species, Trichoderma ma species, Clavibacter species, Glomus species Alternatively, it may be derived from a microorganism such as Gliocladium species. The present invention relates to the identification of at least one heterologous gene derived from Bacillus sp. It is particularly suitable for treating transgenic seeds containing the heterologous gene. More preferably, Bacillus thuringiensis iensis).

[0309] In the context of the present invention, the compounds of formula (I) are applied to seeds, which are Preferably, the processing is carried out in a sufficiently stable state that no damage occurs during the processing. The seeds can be treated at any time between harvest and sowing. Use seeds that have been separated from the cob, husk, petiole, husk, hair or pulp removed. For example, it is harvested, purified, and then stored until it has a moisture content that allows it to be stored. Alternatively, seeds may be dried and then treated with, for example, water. Seeds that have been dried again after (e.g., primed) can also be used. In the case of rice, seeds are soaked in water, for example, until they reach a specific stage of the rice embryo (pigeon breast stage). It is also possible to use a spore extract, which stimulates germination and makes it more uniform. becomes.

[0310] When treating seeds, care should be taken to ensure that seed germination is not adversely affected or that the resulting plants are not damaged. The amount of the compound of formula (I) applied to the seeds and / or the amount of the compound of formula (I) applied to the seeds to prevent damage In general, care must be taken to select the amount of each additive. This must be ensured, especially in the case of active compounds which may have phytotoxic effects at certain application rates. It must be.

[0311] Generally, the compounds of formula (I) are applied to the seeds in the form of a suitable formulation. Suitable formulations and methods for administering the compounds are known to those skilled in the art.

[0312] The compounds of formula (I) can be used in conventional seed dressing formulations, e.g. solutions, emulsions, as a coating composition for seeds, suspensions, powders, foams, slurries or other coating compositions for seeds, etc. It can be converted into a UV-light formulation. do.

[0313] These formulations can be prepared in known manner by incorporating the compounds of formula (I) in conventional excipients, e.g. , conventional extenders, and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents and further mixing with water, a preservative, a second thickener, an adhesive, gibberellins, etc. It is prepared by mixing with

[0314] Colors that may be present in seed dressing formulations that can be used in accordance with the present invention The coloring agents are all coloring agents customary for such purposes. Dyes that dissolve in water or in water can be used. in B," "CIPigment Red 112," and "CISolve Examples of suitable colorants include those known under the name "Ant Red 1."

[0315] Useful compounds that may be present in seed dressing formulations that can be used in accordance with the present invention include: Suitable wetting agents are all substances which promote wetting which are customary for the formulation of active pesticidal ingredients. Preferably, alkylnaphthalene sulfonates, such as diisopropylnaphthalene For example, sulfonate or diisobutylnaphthalene sulfonate can be used.

[0316] Suitable seed dressings that can be used in accordance with the present invention include: Suitable dispersing and / or emulsifying agents are non-ionic, ionic, All dispersants are anionic and cationic. Preferably, they are nonionic or anionic. A mixture of ionic dispersants or nonionic or anionic dispersants may be used. Suitable non-ionic dispersants include, in particular, ethylene oxide / propylene oxide. oxide block polymers, alkylphenol polyglycol ethers and tris Styrylphenol polyglycol ethers and their phosphorylated derivatives or sulfur Suitable anionic dispersants include, in particular, lignosulfonates, Polyacrylates and arylsulfonate-formaldehyde condensates.

[0317] Antifoaming agents that may be present in seed dressing formulations that may be used in accordance with the present invention The foam inhibitors are all foam inhibitors customary for the formulation of active pesticide ingredients. Corn antifoam and magnesium stearate may be used.

[0318] Preservatives that may be present in seed dressing formulations that can be used in accordance with the present invention An agent is any substance that can be used for that purpose in an agrochemical composition. Examples include dichlorophene and benzyl alcohol hemiformal. .

[0319] A second agent that may be present in a seed dressing formulation that may be used in accordance with the present invention. The thickening agents are all substances which can be used for this purpose in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clay, and and finely divided silica.

[0320] Useful compounds that may be present in seed dressing formulations that can be used in accordance with the present invention include: Suitable adhesives are all customary binders that can be used in seed dressing products. Examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose. Examples include:

[0321] Zybele spp. which may be present in seed dressing formulations which may be used in accordance with the present invention. The gibberellins are preferably gibberellin A1, gibberellin A3 (=gibberellic acid), gibberellin A4 (=gibberellic acid), gibberellin A5 (=gibberellic acid), gibberellin A6 (=gibberellic acid), gibberellin A7 (=gibberellic acid), gibberellin A8 (=gibberellic acid), gibberellin A Gibberellin A4 and gibberellin A7 are particularly preferred; gibberellic acid is particularly preferred. The relins are known (cf. R. Wegler "Chemie der Pfla nzenschutz-and Schadlingsbekampfungsmitt el”,vol.2,Springer Verlag,1970,pp.401-41 2).

[0322] Seed dressing formulations that can be used in accordance with the present invention are suitable for a wide variety of seed types. It can be used directly or after pre-dilution with water to treat the It can be used in concentrate form or diluted with water. Preparations that can be obtained from concentrated formulations by It can be used to dress seeds such as wheat, rye, oats and triticale. It is also used in maize, rice, rapeseed, peas, kidney beans, It can also be used to dress cotton, sunflower, soybean and beet seeds. , or can be used to dress a wide variety of vegetable seeds. Seed dressing formulations or their diluted application forms which can be used according to the invention are , and can also be used to dress the seeds of transgenic plants.

[0323] A seed dressing formulation that can be used in accordance with the present invention or a seed dressing formulation to which water has been added When treating seeds with a use form prepared by adding All conventional mixing equipment is useful. In particular, the procedure for seed dressing is as follows: , placing the seeds into a mixer (which may be operated batchwise or continuously), The specified amount of seed dressing formulation is added either as is or after pre-dilution with water. and mixing until the formulation is evenly distributed on the surface of the seeds. If appropriate, this is followed by a drying step.

[0324] The application rates of the seed dressing formulations that can be used according to the invention can vary within a relatively wide range. It can be considered that the specific content and The application rate of the compound of formula (I) is generally 1 kg of seeds per 1 kg of seeds. The amount is 0.001 to 50 g per kg of seeds, and preferably 0.01 to 15 g per kg of seeds. .

[0325] animal health In the field of animal health, i.e. veterinary medicine, the compounds of formula (I) are Active against parasites, especially ectoparasites or endoparasites. "Endoparasites" specifically include helminths and protozoans (e.g., coccidia). Ectoparasites are typically and preferably arthropods, especially insects or spiders. It is type 2.

[0326] In the field of veterinary medicine, the compound represented by formula (I) is preferred for its toxicity to endothermic animals. The compounds are used in animal breeding and livestock production in domestic animals, breeding animals, zoo animals, research animals, and animal husbandry. Occurrence in laboratory, experimental and domestic animals They are suitable for controlling all developmental stages or parasites that live on plants. exhibits activity against specific developmental stages.

[0327] Agricultural livestock can include, for example: mammals, e.g. Sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer, and , especially cattle and pigs; or poultry, e.g., turkeys, ducks, geese , and in particular chickens; or fish or crustaceans, for example in aquaculture fish or crustaceans; or, optionally, insects, for example bees.

[0328] Domestic animals can include, for example: mammals, e.g. Hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially Dogs, cats, caged birds, reptiles, amphibians, or fish in an aquarium.

[0329] In certain embodiments, a compound of Formula (I) is administered to a mammal.

[0330] In another particular embodiment, the compounds of formula (I) are effective against birds, i.e., caged birds. , or, in particular, to poultry.

[0331] The use of the compounds of formula (I) for controlling animal parasites is to reduce or prevent illness, death and performance ) (in the case of meat, milk, wool, leather, eggs, honey, etc.) It is intended that the result will be more economical and easier animal husbandry and better A healthy animal state can be achieved.

[0332] In relation to the field of animal health, the terms "control" or "prevent" "controlling" in the context of the present invention means that the compound of formula (I) reducing the occurrence of individual parasites in infected animals to harmless levels More specifically, "control" means to be effective in preventing the In the context of the invention, the compounds of formula (I) are capable of killing individual parasites and inhibiting their growth. It means to inhibit or inhibit the growth of.

[0333] Examples of arthropods include, but are not limited to: R: From the order Anoplurida, for example, Haematopinus species atopinus spp.), Linognathus spp. ), Pediculus spp., Phtirus spp. spp.), and Solenopotes spp.; Order Mallophagida and suborder Amblycelina cerina) and the Ischnocerina, e.g. Bovicola spp., Damalina spp. .), Felicola spp.; Lepikentron spp. kentron spp.), Menopon spp., Trichodectes Trichodectes spp., Trimenopon spp. pon spp.), Trinoton spp., Wernechiella Genus species (Werneckiella spp.); Diptera and Nematocerina and the suborder Brachycerina, e.g., Aedes species s spp.), Anopheles spp., Achilotus spp. (Atylotus spp.), Braula spp., Calliphora Calliphora spp., Chrysomyia spp. spp.), Chrysops spp., Cule x spp.), Culicoides spp., Eusimuriu Eusimulium spp., Fannia spp. ), Gasterophilus spp., Glossina spp. Glossina spp., Haematobia spp. , Haematopota spp., Hippobosca spp. obosca spp.), Hybomitra spp., Hydro Hydrotaea spp., Hypoderma spp. spp.), Lipoptena spp., Lucilia spp. ilia spp.), Lutzomyia spp., Melopha Melophagus spp., Morellia sp. p.), Musca spp., Odagmia sp. p.), Oestrus spp., Phi lipomyia spp.), Phlebotomus spp. ), Rhinoestrus spp., Sarcophaga spp. arcophaga spp.), Simulium spp., Stomoxys spp., Tabanus spp. .), Tipula spp., Wilhelmia spp. a spp.), Wohlfahrtia spp.; From the order Siphonapterida, for example, Ceratophilus species tophyllus spp.), Ctenocephalides spp. des spp.), Pulex spp., Tunga spp. spp.), Xenopsylla spp.; From the order Heteropterida, for example, Cim ex spp.), Panstrongylus spp. , Rhodnius spp., Triatoma spp. spp.); and, furthermore, pests of the order Blattaria and Sanitary pests.

[0334] Additionally, in the case of arthropods, examples include, but are not limited to, the following mites: It is: Acari (Acarina) and Metastigmatidae gmata), for example, Argasidae, for example, Argas species (Argas spp.), Ornithodorus spp. ), Otobius spp., Ixodidae, For example, Dermacentor spp., Haemaphysalis Haemaphysalis spp., Hyalomma spp. spp.), Ixodes spp., Rhipicephalus (Boophilus Rhipicephalus (Boophilus) spp., Rhipicephalus Rhipicephalus spp. (the original genus of multi-host mites); Mesostigma In the order Mesostigmata, for example, Ornitho nyssus spp.), Pneumonyssus spp. ), Raillietia spp., Sternostoma spp. ernostoma spp.), Tropilaelapus spp. spp.), Varroa spp.; Actinedidae ida (Prostigmata), for example, Acarapis species spp.), Cheyletiella spp., Demodex spp. Demodex spp., Listrophorus spp. pp.), Myobia spp., Neotrombicula spp. rombicula spp.), Ornithocheyl etia spp.), Psorergates spp., Trombicula spp.; and Acaridae idida (Astigmata), for example, Caloglyphus species hus spp.), Chorioptes spp., Shitojite Cytodites spp., Hypodectes spp. spp.), Knemidocoptes spp., Lamino Laminosioptes spp., Notoedress spp. oedres spp.), Otodectes spp., Pso Psoroptes spp., Pterolic hus spp.), Sarcoptes spp., Trixaca Trixacarus spp., Tyrophagus spp. s spp.).

[0335] Examples of parasitic protozoa include, but are not limited to: Cut: Subphylum Mastigophora (Flagellata), e.g. For example: Metamonada: Diplomonadida a) for example, Giardia spp., Spironucleus spp. (Spironucleus spp.); Parabasala: Trichomonadida a), for example, Histomonas spp., Pentatricho Pentatrichomonas spp., Tetratrichomonas spp. (Tetratrichomonas spp.), Trichomonas spp. onas spp.), Tritrichomonas spp. ); Euglenozoa: Order Trypanosoma atida), for example, Leishmania spp., Trypanosoma spp.; Sarcomastigophora (Rhizopodia) da)), for example, Entamoebidae, for example, Entamoebidae Entamoeba spp., Centramo ebidae), e.g., Acanthamoeba sp., Euamoebidae, e.g., Hartmanella species nella sp.); Alveolata, e.g., Apicomplexa mplexa) (Sporozoa), e.g., Cryptosporidium spp. (Cryptosporidium spp.); Eimeriida For example, Besnoitia spp., Cystoisospora spp. Cystoisospora spp., Eimeria sp. p.), Hammondia spp., Isospora spp. pora spp.), Neospora spp., Sarcocystis Sarcocystis spp., Toxoplasma spp. ma spp.); Adeleida, e.g., Hepatozoon spp. Hepatozoon spp.), Klossiella spp. ); Haemosporida, e.g., Leucocytozoon species (Leucocytozoon spp.), Plasmodium spp. m spp.); from the order Piroplasmida, for example Babesia Babesia spp., Ciliophora spp. ), Echinozoon spp., Theileria spp. leria spp.); examples of Vesibuliferida For example, Balantidium spp., Buxtonella spp. Buxtonella spp.); Microspora, e.g., Encephalitzoon species ephalitozoon spp.), Enterocytozoon spp. ozoon spp.), Globidium spp., Nosema Nosema spp. and also, for example, Myxozoa spp. zoa spp.).

[0336] Helminths that are pathogenic to humans or animals include, for example, Acanthocephalans. thocephala), Nematoda, Pentastoma and Platymorpha Platyhelminthes (e.g. Monogenea, Platyhelminthes) Examples include insects (cestodes) and trematodes.

[0337] Exemplary helminths include, but are not limited to: : Monogenea: for example: Dactylogyr us spp.), Gyrodactylus spp., Mik Microbothrium spp., Polistoma spp. ystoma spp.), Troglecephalus spp. spp.); Cestodes: Pseudophyllides a) for example: Bothridium spp., Diphyllobot Diphyllobothrium spp., Diphlogonoporus spp. Diplogonoporus spp., Ichthyobothrium spp. bothrium spp.), Ligula spp., Cysticepha Schistocephalus spp., Spirometra spp. ometra spp.); In the order Cyclophyllida, for example: Andira species ( Andyra spp.), Anoplocephala sp. p.), Avitellina spp., Berchiella spp. tiella spp.), Cittotaenia spp., Davainea spp., Diorchis spp. spp.), Diplopylidium spp., Dipyli Dipylidium spp., Echinococcus spp. occus spp.), Echinocotyle spp., Echinolepis spp., Hydat igera spp.), Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp. Mesocestoides spp., Moniezia spp. .), Paranoplocephala spp., Rai Raillietina spp., Stilesi spp. a spp.), Taenia spp., Thy saniezia spp., Thysanosoma spp. ; Trematodes: of the Digenea subclass, e.g., Aust Austrobilharzia spp., Brachyraema spp. (Brachylaima spp.), Calicophoron spp. spp.), Catatropis spp., Chronorchis spp. Clonorchis spp., Collyriclum spp. spp.), Cotylophoron spp., Cyclocoelia Cyclocoelum spp., Dicroco elium spp.), Diplostomum spp., Echinochasmus spp., Echinopalphium spp. species (Echinoparyphium spp.), Echinos toma spp.), Eurytrema spp., Fasciola Fasciola spp., Fasciolides spp. s spp.), Fasciolopsis spp., Fischoederius spp., Gastrothyrax spp. (Gastrothylacus spp.), Gigantobilharzia spp. tobilharzia spp.), Gigantocotyl spp. e spp.), Heterophyes spp., Hypodera Hypoderaeum spp., Leucchloridium spp. ochloridium spp.), Metagonimus spp. pp.), Metorchis spp., Nanophyetus spp. anophyetus spp.), Notocotylus sp. p.), Opisthorchis spp., Ornithobilus Ornithobilharzia spp., Paragonimus spp. ragonimus spp.), Paramphistomum spp. um spp.), Plagiorchis spp., Post Posthodiplostomum spp., Prostgoni Prosthogonimus spp., Schistosoma spp. osoma spp.), Trichobilharzia spp. spp.), Troglotrema spp., Typhlocoel Typhlocoelum spp.; Nematodes: examples of Trichinellida For example: Capillaria spp., Trichinella spp. hinella spp.), Trichomosoides spp. spp.), Trichuris spp.; From the order Tylenchida, for example: Micronema species nema spp.), Parastrangyloides spp. es spp.), Strongyloides spp. ; From the order Rhabditina, for example: Aerulostrongylus spp. (Aelurostrongylus spp.), Amidostomum spp. tomum spp.), Ancylostoma spp., Angiostrongylus spp., Bronco Bronchonema spp., Bunostom um spp.), Chabertia spp., Kooperia spp. (Cooperia spp.), Cooperioides spp. spp.), Crenosoma spp., Cyatostomum spp. Cyathostomum spp., Cyclococcus spp. cus spp.), Cyclodontostomum spp. spp.), Cyclocercus spp., Cylicocyclus Stephanus spp., Cylindrophallinchi Cylindropharynx spp., Cyst ocaulus spp.), Dictyocaulus sp. p.), Elaphostrongylus spp., Filaroides spp., Globocephalus spp. obocephalus spp.), Graphidium spp. pp.), Gyalocephalus spp., fly Haemonchus spp., Heligmosomoides spp. osomoides spp.), Hyostrongylus spp. s spp.), Marshallagia spp., Metas Metastrongylus spp., Muellerius spp. uellerius spp.), Necator spp., Nemato Nematodirus spp., Neos trongylus spp.), Nippostrongylus spp. ylus spp.), Obeliscoides spp. , Oesophagodontus spp., Oesophagodontus Oesophagostomum spp., Orlanus spp. Ornithostrongylus spp.; Ornithostrongylus spp. ngylus spp.), Oslerus spp., Osterta Ostertagia spp., Paracooperia spp. eria spp.), Paraclenosoma spp. , Parafilaroides spp., Parafilahost Parelaphostrongylus spp., Pneumocau Pneumocaulus spp., Pn eumostrongylus spp.), Poteriostomum spp. tomum spp.), Protostrongylus spp. spp.), Spicocaulus spp., Stephane Stephanurus spp., Strongy lus spp.), Syngamus spp., Terradorsagia Teladorsagia spp., Trichonema spp. spp.), Trichostrongylus spp. .), Triodontophorus spp., Trog Troglostrongylus spp., Uncinaria genus species (Uncinaria spp.); From the order Spirurida, for example: Acanthocheironema species (A canthocheilonema spp.), Anisakis spp. spp.), Ascaridia spp.; Ascaris spp. scaris spp.), Ascarops spp., Aspi Aspiculuris spp., Baylisascaris spp. isascaris spp.), Brugia spp., Cercopi Cercopithifilaria spp., Crassicauda spp. Crassicauda spp., Dipetalonema spp. a spp.), Dirofilaria spp., Drakun Dracunculus spp.; Draschia spp. spp.), Enterobius spp., Filaria spp. species (Filaria spp.), Gnathostoma spp. .), Gongylonema spp., Habronema spp. bronema spp.), Heterakis spp.; Litomosoides spp., Loa spp. ), Onchocerca spp., Oxy uris spp.), Parabronema spp., Para Parafilaria spp., Paras caris spp.), Passalurus spp., Physa Physaloptera spp., Probstomaillia spp. obstmayria spp., Pseudofilaria spp. ia spp.), Setaria spp., Scutella spp. (Skjrabinema spp.), Spirocerca spp. pp.), Stephanofilaria spp., Strongyluris spp., Syph acia spp.), Thelazia spp., Toxascaris Toxascaris spp., Toxocara spp. .), Wuchereria spp.; Phylum Acanthocephala: Order Oligocene anthorhynchida, for example: Macracanthrynx species anthorhynchus spp.), Prosthenorchis spp. rchis spp.); Moniliformida , for example: Moniliformis spp.; From the order Polymorphida, for example: Fil icollis spp.); of the order Echinorhynchida For example, Acanthocephalus spp. Echinorhynchus spp., Leptorhynchoides spp. species (Leptorhynchoides spp.); Phylum Pentastoma: Order Porocephalid a), for example, Linguatula spp.

[0338] In the field of veterinary medicine and in animal husbandry, compounds of formula (I) are useful in the art. By methods generally known in the art, for example, in the form of a suitable preparation, Administration is via the enteral, parenteral, transdermal or nasal route. , post-infection protective (metaphylactic) or therapeutic.

[0339] Therefore, one embodiment of the present invention provides a compound of formula (I) for use as a medicament. Pertaining to things.

[0340] A further aspect relates to compounds of formula (I) for use as anti-endoparasitic agents. Regarding.

[0341] A further particular embodiment of the present invention is an antihelminthic agent. In particular, for use as nematicides, flatwormicides (platyhelmin thicide, acanthocephalicide or lingulicide A compound of formula (I) for use as a pentastomicide Concerning compounds.

[0342] A further particular embodiment of the present invention is directed to the use of antiprotozoan agents. t) a compound of formula (I) for use as a

[0343] A further aspect is the use of the compound as an anti-ectoparasite, in particular as an arthropodicide (ar for use as a thropodicide, very particularly as an insecticide or fungicide The present invention relates to a compound of formula (I) for use as an acaricide.

[0344] A further aspect of the present invention is a method for treating a rheumatoid arthritis comprising administering to a subject a composition comprising an effective amount of at least one compound of formula (I) and and at least one of the following: a pharmaceutically acceptable excipients (e.g., solid or liquid diluents), pharmaceutically acceptable adjuvants (e.g., surfactants), especially pharmaceutically acceptable surfactants customarily used in veterinary drug formulations. and / or pharmaceutically acceptable excipients customarily used in veterinary drug formulations. Aids in obtaining.

[0345] A related aspect of the invention is a method for producing the veterinary pharmaceutical formulations described herein. wherein the method comprises administering at least one compound of formula (I) to a pharmaceutically acceptable carrier. acceptable excipients and / or adjuvants (especially those customarily used in veterinary drug formulations) Pharmaceutically acceptable excipients and / or excipients customarily used in veterinary drug formulations The method includes mixing the composition with a pharmaceutically acceptable excipient.

[0346] Another particular embodiment of the present invention is an ectoparasiticide formulation according to the above embodiment. parasiticide formulations and endoparasiticide formulations Veterinary drugs selected from the group consisting of oparasiticidal formulations Preparations, in particular anthelmintic preparations, antiprotozoic preparations lations and arthropodicidal forms Veterinary medicinal preparations selected from the group of veterinary medicines, most especially nematicidal preparations, flatworm-killing preparations veterinary drug formulations (platyhelminthicidal formulations), Acanthocephalic formulation s), pentastomicidal formulations ), veterinary drug formulations selected from the group consisting of insecticide formulations and acaricide formulations, and methods for producing them. This is a method of making it.

[0347] Another aspect is the treatment of parasitic infections, particularly the ectoparasites and endoparasites described above. and a method for treating an infection caused by a parasite selected from the group consisting of: and administering an effective amount of a compound of formula (I) to an animal (particularly a non-human animal) in need of such treatment. By using compounds that are

[0348] Another aspect is the treatment of parasitic infections, particularly the ectoparasites and endoparasites described above. and a method for treating an infection caused by a parasite selected from the group consisting of: and the like, as defined herein, in animals (particularly non-human animals) in need of such treatment. By using veterinary drug preparations that are approved for use in animals.

[0349] Another aspect is directed to the treatment of parasitic infections in animals (particularly non-human animals), particularly those described above. Treatment of infections caused by parasites selected from the group of ectoparasites and endoparasites The present invention relates to the use of a compound of formula (I) in

[0350] In the context of animal health or veterinary medicine, the term "treatment" refers to preventive treatment. This includes post-infection prophylactic or therapeutic treatment.

[0351] In a particular embodiment, the veterinary field is thus provided with a compound of formula (I): and at least one compound to be used in combination with another active compound (particularly an endoparasiticide and an ectocide). A mixture of anti-parasitic drugs is provided.

[0352] In the field of animal health, a "mixture" is a mixture of two (or more) different It only means that the active compounds are formulated in a co-preparation and thereby used together. It also relates to products that contain separate formulations for each active compound, rather than a single formulation. Therefore, when three or more active compounds are used, all active compounds should be formulated in a common formulation. Alternatively, all active compounds can be formulated in separate formulations. Similarly, some of the active compounds may be formulated together and some of the active compounds may be formulated separately. In separate formulations, the active compounds may be mixed. can be applied separately or can be applied sequentially.

[0353] Active ingredients identified herein by "common name" are known and and as described, for example, in the "Pesticide Manual" (see above). or can be found on the internet (e.g. http: / / www.alanwood.net / pesticides ).

[0354] Exemplary active compounds selected from the group of ectoparasiticides as mixture components include: Although not intended to be limiting in any way, the insecticides detailed above Further active compounds that can be used include insecticides and acaricides. Regarding the current "IRAC Mode of Action Classification" According to the above classification based on the "ion scheme", they are described as follows: (1) Acetyl (2) GABA-regulated chloride channel blockers; (3) Sodium channel modulators; (4) Nicotinic acetylcholine receptors (5) Nicotinic acetylcholine receptor (nAChR) competitive modulators nAChR) allosteric modulators; (6) glutamate-regulated chloride channels (GluCl) allosteric modulators; (7) juvenile hormone mimetics; (8) species (9) Chordotonal organ modulators; (10) Mites Growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, e.g., ATP synthase inhibitors Raptor; (13) an uncoupler of oxidative phosphorylation by disrupting the proton gradient; (1 4) Nicotinic acetylcholine receptor channel blockers; (15) Chitin biosynthesis inhibitors (16) Chitin biosynthesis inhibitors (Type 1); (17) Molting disruptors (18) Ecdysone receptor agonists; (19) Octopus (21) Mitochondrial complex I electron transport inhibitors; (25) Mitochondrial Mitochondrial complex II electron transport inhibitors; (20) Mitochondrial complex III electron transport inhibitors (22) Voltage-dependent sodium channel blockers; (23) Acetyl-CoA carboxylates enzyme inhibitors; (28) ryanodine receptor modulators; Active compounds with unknown or unspecified mechanisms of action, e.g., phentrile Phanil, Fenoxacrim, Cycloprene, Chlorobenzilate, Chlordimeform, Flubenzimine, dicyclanil, amidoflumet, chinomethionate, triatene, chlorpheniramine Rothiazoben, Tetrasulfur, Potassium Oleate, Petroleum, Methoxadiazone, Gossypium , flutensin, bromopropylate, cryolite; Another class of compounds, e.g., butacarb, dimethylane, cloethocarb, phosphocarb bu, pirimiphos (-ethyl), parathion (-ethyl), methacrifos, o-salicylic acid Isopropyl, trichlorfon, tigoraner, sulprofos, propafos, cevufos, pi Lidathione, Protoate, Diclofenthion, Demeton-S-methylsulfone, Isa Zophos, Cyanofenphos, Diarifos, Carbophenothion, Autathiofos, Arom Fenvinphos (-methyl), azinphos (-ethyl), chlorpyrifos (-ethyl), Fosmetiran, iodofenphos, dioxabenzophos, formothion, fonofos, fluoxetine pyrazophos, fensulfothion, etrimphos; Organochlorines, such as camphechlor, lindane, heptachlor; or phenyl fluprole, pyrifluprole, pyriprole, vanillin, or isoxazolines, e.g., sarolaner, afoxoxo Ranel, Lotiranel, Fluralaner; Pyrethroids, such as (cis-, trans-) metofluthrin, profluthrin, Flufenprox, flubrocythrinate, fubufenprox, fenflutri Protrifenbut, Pyresmethrin, RU15525, Teralethrin, Cis-less Methrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyritri cis-cypermethrin, cis-permethrin, clocithrin, cyhalothrin (lambda -), clovaporthrin, or halogenated hydrocarbon compounds (HCHs); Neonicotinoids, for example, nithiazine; Dichloromezotiaz, triflumezopyrim; Macrocyclic lactones, such as nemadectin, ivermectin, latidectin, moxide Cutin, Selamectin, Eprinomectin, Doramectin, Emamectin Benzoate; rubemycin oxime; Triplene, epofenonane, diofenolan; Biological agents, hormones, or pheromones, e.g., natural products, e.g., thuringiensin, codlemone, or neem compounds; Dinitrophenols, such as dinocap, dinobuton, binapacryl; Benzoylureas, for example, fluazuron, penfluron; Amidine derivatives such as chlormebuform, cymia Zoll, Demiditraz; Beehive Varroa destructor miticide (beehive varroa acari cides), for example, organic acids, for example, formic acid, oxalic acid.

[0355] Exemplary active compounds selected from the group of endoparasiticides as mixture components include: These include, but are not limited to, anthelmintic active ingredients and antiprotozoan active ingredients. Cut.

[0356] The anthelmintic active compound includes, but is not limited to, the following nematicidal active compounds, suction-killing compounds, Examples include compounds with insecticidal and / or cesticidal activity: From the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Mil Bemectin, ivermectin, emamectin, milbemycin; From the class of benzimidazoles and probenzimidazoles, for example: oxybenzimidazoles oxibendazole, mebendazole, triclabendazole riclabendazole, thiophanate, parbe parbendazole, oxfendazole le), netobimin, fenbendazole, febantel, thia Thiabendazole, cyclobendazole, cambendazole , albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably from the class of cyclic depsipeptides, in particular The class of 24-membered cyclic depsipeptides, for example: emodepsid e), PF1022A; From the class of the tetrahydropyrimidines, for example: morantel, pyrantel, oxanthine Le; From the class of the imidazothiazoles, for example: butamisole, levamisole, tetramiso Rule; From the class of aminophenylamidines, for example: amidantel, deacylated amidantel le (dAMD), tribendimidine; From the class of aminoacetonitriles, for example: monepantel ; From the class of the paraherquamides, for example: paraherquamide, delquantel; From the class of salicylanilides, for example: tribromosalan, bromoxanide, bromine Anide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxa Nido; From the class of substituted phenols, for example: nitroxynil, bithionol, diisophenone hexachlorophene, niclofolan, meniclofolan ); From the class of organophosphates, for example: trichlorfon, naphthalophos (naph thalofos), dichlorvos / DDVP, crufomate, coumaphos, haloxone; From the class of piperazinones / quinolines, for example: praziquantel antel), epsiprantel; From the class of piperazines, for example: piperazine, hydroxyzine; From the class of tetracyclines, for example: tetracycline, chlorotetracycline , doxycycline, oxytetracycline, rolitetracycline; Various other classes, for example: bunamidine, niridazole, resolantel, omuf Arothrin, Oltipraz, Nitroscanate, Nitroxynil, Oxamniquine, Mirasa Mirasan, miracil, lucanton, hycanton, hetri Hetolin, emetine, diethylcarbamazine, dichlorophen, diamphen Netide, clonazepam, bephenium, amoscanate, clo Ruslon.

[0357] Active antiprotozoan components include, but are not limited to, the following active compounds: You can: From the class of triazines, for example: diclazuril, ponazuril, letrazuril, tort Razuril; From the class of polyether ionophores, for example: monensin, salinomycin, madu Ramycin, Narasin; From the class of macrocyclic lactones, for example: milbemycin, erythromycin; From the class of quinolones, for example: enrofloxacin, pradofloxacin; From the quinine class, for example: chloroquine; From the class of pyrimidines, for example: pyrimethamine; From the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfonamides phaclozin; From the class of thiamines, for example: amprolium; From the class of lincosamides, for example: clindamycin; From the class of carbanilides, for example: imidocarb; From the class of nitrofurans, for example: nifurtimox; From the class of quinazolinone alkaloids, for example: halofuginone; Of various different classes, for example: oxamniquine, paromomycin; of the class of vaccines or microbial antigens, for example: Babesia canis rossi (Bab esia canis rossi), Eimeria tenera lla), Eimeria praecox, Eimeria Eimeria necatrix, Eimeria mitis ria mitis), Eimeria maxima, Eimeria brunetti, Eimeria acervulina (Eimeria acervulina), Babesia canis bogeri (Babesi a canis vogeli), Leishmania infantum (Leishman ia infantum), Babesia canis canis, Dictyocaulus vivip arus).

[0358] All mixture components described may be optionally mixed, if possible, based on their functional groups. It is also possible to form salts with suitable bases or acids.

[0359] Vector control The compounds of formula (I) may be used in the control of vectors. In the context of the present invention, vectors are animals that carry pathogens (e.g., viruses, helminths ( worms, single-celled organisms and bacteria) from their reservoirs (plants, animals, humans, etc.) The pathogen is an arthropod (especially an insect or arachnid) that can carry the pathogen from the host to the host. The body may be mechanically transported to the host (e.g., trachoma caused by non-biting flies), or They can be carried after injection into the host (e.g., malaria parasites by mosquitoes).

[0360] Examples of vectors and the diseases or pathogens they carry are: R: 1) Mosquitoes Anopheles mosquitoes: malaria, filariasis; Culex: Japanese encephalitis, filariasis, other viral diseases, other Carrying helminths; Aedes mosquitoes: Yellow fever, dengue fever, other viral diseases, filariasis disease; Black flies (Simuliidae): helminths (especially Onchocerca a volvulus)) transport; · House flies (Psychodidae): transmission of leishmaniasis; 2) Lice: skin infections, epidemic typhus; 3) Fleas: infectious diseases, typhus, tapeworms; 4) Flies: sleeping sickness (trypanosomiasis); cholera, another bacterial disease; 5) Mites: Acariosis, epidemic typhus, rickettsial smallpox, stink bugs Rabbit disease, St. Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, Borrelia borreliosis; 6) Ixodes: Borreliosis (borellioses), e.g., Lyme disease Borrelia ( Borrelia bungdorferi sensu lato.), Dutton regression Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiel la burnetii), babesiosis (Babesia c anis canis, ehrlichiosis.

[0361] In the context of the present invention, examples of vectors are insects capable of transmitting plant viruses to plants, For example, aphids, flies, leafhoppers or thrips. Other vectors that can carry the virus are spider mites, lice, beetles and nematodes. .

[0362] In the context of the present invention, further examples of vectors are those that carry pathogens to animals and / or humans. insects and arachnids capable of killing insects, such as mosquitoes (particularly Aedes mosquitoes of the genus Anopheles, e.g., Anopheles gambiae (Ag ambiae), Anopheles arabiensis (A.arabiensis), Anopheles A. funestus, A. dirus ) (malaria), and Culex mosquitoes, Psych flies odidae), e.g., Phlebotomus sandflies, L utzomyia), lice, fleas, flies, mites and ticks.

[0363] The compounds of formula (I) break down resistance ng), vector control is also possible.

[0364] The compounds of formula (I) are useful in the prevention of disease and / or vector-borne diseases. Thus, a further aspect of the invention is suitable for use in the prevention of infectious diseases, e.g. For example, in agriculture, horticulture, forests, gardens and leisure facilities, and and furthermore, compounds of formula (I) for controlling vectors in the protection of materials and stored products. The use of a compound represented by the formula:

[0365] Protection of industrial materials The compounds of formula (I) can be used to treat insects (e.g., Coleoptera ), Hymenoptera, Isoptera, Lepidoptera Lepidoptera), Psocoptera and Zygoptera Suitable for protecting industrial materials against attack or destruction by insects (e.g., scleractinian mollusks ... is doing.

[0366] In the context of the present invention, industrial materials are non-biological materials, such as, preferably, plastics, adhesives, etc. This means adhesives, sizes, paper and cardboard, leather, wood, engineered wood products and paints. It is understood that the present invention is particularly preferably used to protect wood.

[0367] In a further embodiment, the compound of formula (I) is Use in conjunction with an insecticide and / or at least one fungicide.

[0368] In a further embodiment, the compound of formula (I) is a ready-to-use This means that they are in the form of pesticides that can be further modified. This means that it can be applied to the material without any need for further treatment. Insecticides or fungicides that comprise these include, inter alia, those listed above.

[0369] Surprisingly, the compounds of formula (I) are suitable for use in those in contact with seawater or freshwater, especially seawater. In addition, the hull, screens, nets, structures, mooring equipment and signalling systems must be protected from fouling. Similarly, it has been found that the compound represented by formula (I) can be used to protect against The compounds can be used as antifouling agents alone or in combination with other active compounds. Cut.

[0370] Pest control in the sanitation sector The compounds of formula (I) are suitable for controlling pests in the hygiene sector. In particular, the invention is useful in the field of domestic protection, in the field of hygiene protection and in storage. In the protection of products, in particular in enclosed spaces (e.g., dwellings, factory corridors, offices, vehicles) Insects, arachnids, ticks and mites encountered in the facility (guest rooms, animal breeding facilities) In order to control pests, the compound represented by formula (I) can be used. The product may be used alone or in combination with other active compounds and / or auxiliaries. They are preferably used in household insecticide products. The compounds are effective against sensitive and resistant species and at all developmental stages. It is effective against.

[0371] These pests include, for example, Scorpions of the Arachnida class. piones), Araneae and Opiliones pests of the classes Chilopoda and Diplopoda , Insecta, Blattodea, Coleoptera leoptera), Dermaptera, Diptera ), Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera thiraptera), Psocoptera, Orthoptera tatoria or Orthoptera), Siphonaptera and and Zygentoma pests, as well as Malacostraca pests. Examples of pests include those of the order Isopoda.

[0372] Application may be by aerosol, non-pressurized spray products, such as pump sprays and sprayers. Fog spray, automatic fogging system , foggers, foams, gels, cellulose or plastic evaporators Evaporator products with evaporator tablets, liquid evaporators, gel and membrane evaporators propeller-driven evaporators, energy-free evaporation systems or passive evaporation systems stems, moth papers, moth bags and In moth gels or as granules or powders This can be done in broadcast bait or at a bait station.

[0373] analytical measurements The analytical measurement procedures described below are used in individual parts of the specification to determine specific analytical procedures. Unless specific descriptions of measurement procedures are given, all information throughout this specification Regarding the news.

[0374] mass spectrometry [M+H] using LC-MS under acidic chromatographic conditions + or M - Measurement of The eluent was 1 mL of formic acid per liter of acetonitrile and 1 liter of This was done using 0.9 mL of formic acid per Millipore water. Plus C18 50mm x 2.1mm, 1.8µm column in a column oven. A temperature of 55°C was used.

[0375] device: LC-MS3 :SQD2 mass spectrometer and SampleManager sample changer Waters UPLC with a linear gradient of 0.0 to 1.70 min, 10% acetone. Nitrile → 95% acetonitrile, 1.70 → 2.40 min constant 95% acetonitrile, Flow rate: 0.85mL / min.

[0376] LC-MS6 and LC-MS7 :Agilent 1290LC, Agilent MSD mass spectrometer, HTS PAL sample changer. Linear gradient: 0.0 → 1.80 Minutes: 10% acetonitrile → 95% acetonitrile, 1.80 → 2.50 min, constant 95% Acetonitrile, flow rate: 1.0 mL / min.

[0377] [M+H] using LC-MS under neutral chromatographic conditions + The measurement of eluent Acetonitrile and Millipore water (containing 79 mg / L ammonium carbonate) were used as the solvent. This was carried out using

[0378] device: LC-MS4 :Wate with QDA mass spectrometer and FTN sample changer rs IClass Acquity (column Waters Acquity 1.7 μm 50mm x 2.1mm, column oven temperature: 45℃. Linear gradient: 0.0 → 2. 10 min 10% acetonitrile → 95% acetonitrile, 2.10 → 3.00 min constant 9 5% acetonitrile, flow rate: 0.7 mL / min.

[0379] LC-MS5 : Equipped with an MSD mass spectrometer and HTS PAL sample changer Agilent 1100 LC System (Column: Zorbax XDB C1 8 1.8 μm 50 mm × 4.6 mm, column oven temperature: 55 °C. Linear gradient: 0 0 → 4.25 min 10% acetonitrile → 95% acetonitrile, 4.25 → 5.80 min Constant 95% acetonitrile, flow rate: 2.0 mL / min.

[0380] In all cases, the retention time index is calculated for homologous members with 3 to 16 carbons. Determined from calibration measurements of a series of straight-chain alkan-2-ones, where Set the index to 300 and the index for the last arcanon to 1600. The values ​​were then linearly interpolated between successive alkanone values.

[0381] 1 H NMR spectra were measured using a Br NMR spectrometer equipped with a 1.7 mm TCI sample head. A BMW Avance III 400MHz spectrometer showed a typical value of 0.00 ppm. Using tetramethylsilane as the solvent, CD3CN, CDCl3 or d6-DMS Alternatively, a 5 mm CPNMP sample head was used with a Br Ker Avance III 600MHz Spectrometer or 5mm TCI Sample The Bruker Avance NEO 600MHz spectrometer equipped with a holographic head was used. Generally, the measurements were carried out at a sample head temperature of 298 K. Where different measurement temperatures were used, this is noted separately.

[0382] NMR peak list method Selected Examples 1 H NMR data is 1 Shown in the form of a H NMR peak list For each signal peak, the δ value (ppm) is listed first, followed by the The signal intensities are listed in δ values ​​for various signal peaks - signal intensity. Pairs of numbers are listed, separated from each other by semicolons.

[0383] Thus, the peak list for one example takes the form: δ1(Intensity 1);δ2(Intensity 2);...;δ i (strength i );...;δ n (strength n ).

[0384] The intensity of the sharp signal is determined by the signal height ( cm) and indicates the true ratio of signal intensities. For broad signals, several The peaks or centers of the signals and their relative intensities are It can be shown relative to the strongest signal.

[0385] 1 Tetramethylsilane is used to calibrate the chemical shifts of the H NMR spectra. or, if the sample does not contain tetramethylsilane, use the chemical shift of the solvent. Thus, in some cases, the NMR peak list may include the peak for tetramethylsilane. do.

[0386] 1 The list of H NMR peaks is given in the conventional 1 It is similar to the H NMR representation, and therefore, It usually includes all peaks described in conventional NMR interpretation.

[0387] Furthermore, they are 1 As shown in the H NMR representation, the solvent signal, The signals and / or stereoisomers of the compounds, which may be provided by the present invention, or peak signals of impurities may also be shown.

[0388] The NMR solvent signals, the tetramethylsilane peaks and the water signals in the solvent in question are Their reported intensity values ​​can be so high that they are excluded from the relative intensity calibration.

[0389] Peaks of (stereo)isomers and / or impurity peaks of the compounds of the present invention are usually have on average lower intensities than the peaks of bright compounds (e.g., with a purity of >90%).

[0390] Such stereoisomers and / or impurities may be specific to a particular preparation method. Therefore, these peaks are called "by-product fingerprints." Regarding "prints," this may help to confirm the reproducibility of our preparation method.

[0391] The peaks of the target compounds were identified using known methods (MestreC, ACD simulation, and Experts who calculate using empirically evaluated expected values ​​may add additional costs if necessary. A typical intensity filter can be used to isolate the peaks of the target compounds. This is analogous to picking relevant peaks in conventional interpretation of 1H NMR. There will be.

[0392] The JCAMP database includes the solvent used, the spectrometer measurement frequency, and the spectrometer model. The parameters "solvent", "frequency observation", and "spectrometer / data system" are respectively can be found using

[0393] 13 C NMR data is broadband separated 13 Peak list using C NMR spectrum as 1 The NMR solvent signals and Tetramethylsilane can be used to measure the relative intensity of these signals, as they may have relatively high intensity values. are excluded from the calibration.

[0394] 1 Further details of the H NMR peak list can be found in Research Disclosure. e "Citation of Database Number 564025" NMR Peaklist Data within Patent Application ons".

[0395] logP value The logP value is based on the EEC Directive 79 / 83 Annex V.A8. Therefore, the following method was used to perform HPLC (High Performance Liquid Chromatography) on a reversed phase column (C18). Graphy) was measured: [a] The logP values ​​were 0.9 ml / L formic acid in water and 1.0 ml / L in acetonitrile. It was determined by LC-UV measurement in the acidic range using formic acid as the mobile phase (acetone). linear gradient from 10% nitrile to 95% acetonitrile).

[0396] [b] The log P values ​​were calculated using 79 mg / L ammonium carbonate in water and acetonitrile as the mobile phase. Measured by LC-UV in the neutral range (10% acetonitrile to 95% acetonitrile) linear gradient to the rill).

[0397] Calibration was performed using linear alkan-2-ones (3 to 16 carbon atoms) with known logP values. The values ​​between successive alkanones were calculated by linear regression. is determined. [Example]

[0398] Preparation Examples: 7-Bromo-4-ethylsulfonyl-3-[3-methyl-6-(trifluoromethyl) Imidazo[4,5-b]pyridin-2-yl]isoquinoline (I-37) [ka]

[0399] 0.10 g (2.14 mmol) formic acid and 0.34 g (3.00 mmol, 30% Strength) hydrogen peroxide in 10 ml of dichloromethane. 7-Bromo-4-ethylsulfanyl-3-[3-methyl-6-(trifluoroethyl) The resulting solution was added to a solution of imidazo[4,5-b]pyridin-2-yl]isoquinoline. The mixture was stirred at room temperature for 6 hours, then diluted with aqueous Na2S2O3 and added to 30 mL of dichloromethane. The organic phase was dried over sodium sulfate, filtered and rotary evaporated. The residue was purified by preparative high-performance liquid chromatography (mobile phase: MeCN / H2O ) and purified.

[0400] Analytical data: See peak list 7-Bromo-4-ethylsulfanyl-3-[3-methyl-6-(trifluoroethyl) )Imidazo[4,5-b]pyridin-2-yl]isoquinoline [ka]

[0401] 10.0 g (162 mmol) EtSH, 2.50 g (2.40 mmol) Pd2 (dba)3·CHCl3, 2.80 g (4.90 mmol) of Xantphos, and 6 0.30 g (48 mmol) of Hunig's base in 50 ml of 1,4-dioxane. 00g (16.2mmol) of [7-bromo-3-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]-4-isoquinolyl]trifluoro The reaction mixture was stirred at 80° C. for 16 hours. Quench the mixture by adding 100 ml of water and ethyl acetate (2 x 150 The organic phase was washed with saturated aqueous NaCl, dried over sodium sulfate, and The resulting crude product was purified by silica gel column chromatography ( The mixture was purified with pentane / ethyl acetate (8:1).

[0402] 1 H-NMR(400 Mhz, D6-DMSO) δ ppm: 9.51 (s, 1H), 8.87 (s, 1H), 8.70 (s, 1H), 8.69 (s, 1H), 8.56 (d, 1H), 8.19 (d, 1H), 3.77 (s, 3H), 2.84 (q, 2H), 0.98 (t, 3H). [7-bromo-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b ]pyridin-2-yl]-4-isoquinolyl]trifluoromethanesulfonate [ka]

[0403] 6.70 g (23.6 mmol) of trifluoromethanesulfonic anhydride in 15 ml 1.00 g (2.40 mmol) of 7-bromo-3-[3-methyl-6- (Trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]isoquinoline-4 The resulting reaction mixture was stirred at room temperature for 16 hours, after which NaHC The mixture was extracted with 30 ml of ethyl acetate, and the organic phase was diluted with sodium sulfate. The resulting crude product was purified by silica gel column chromatography. The mixture was purified by a mixture of petroleum ether / ethyl acetate (8:1).

[0404] 1 H-NMR(400 Mhz, D6-DMSO) δ ppm: 9.67 (s, 1H), 8.93 (s, 1H), 8.85 (s, 1H), 8.72 (s, 1H), 8.36 (d, 1H), 8.14 (d, 1H), 4.08 (s, 3H). 7-Bromo-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b] Pyridin-2-yl]isoquinolin-4-ol [ka]

[0405] 17.2 g (89.7 mmol) of EDCI and 2.00 g (14.8 mmol) of HOBt was prepared by dissolving 15.7 g (82.2 mmol) of N in 40 mL of CHCN. 2 -methyl -5-(trifluoromethyl)pyridine-2,3-diamine, 15.7 g (74.9 mm ol) 7-bromo-4-hydroxyisoquinoline-3-carboxylic acid and 20 mL of The resulting reaction mixture was stirred at room temperature for 16 hours, and then 100 The mixture was quenched with 1 ml of water and extracted with ethyl acetate (2 x 400 ml). The organic phase was washed with sodium sulfate The resulting residue was dissolved in 40 ml of HOAc and then The mixture was stirred at 80° C. for 16 hours. The mixture was quenched by the addition of 100 ml of water and acetic acid. The organic phase was washed with saturated aqueous NaCl and extracted with sodium sulfate. The crude product was purified by silica gel column chromatography. The mixture was purified by chromatography (petroleum ether / ethyl acetate=5:1).

[0406] 1 H-NMR(400 Mhz, D6-DMSO) δ ppm: 9.03 (s, 1H), 8.88 (s, 1H), 8.71 (s, 1H), 8.53 (s, 1H), 8.32 (d, 1H), 8.10 (br, 1H), 8.03 (d, 1H), 4.48 (s, 3H). 7-Bromo-4-hydroxyisoquinoline-3-carboxylic acid [ka]

[0407] 12.0 g (40.7 mmol) of 7- in 30 ml of methanol / H2O (7:1) Ethyl bromo-4-hydroxyisoquinoline-3-carboxylate and 3.30 g (81.4 m The mixture was stirred at 50°C for 2 hours. The reaction mixture was then diluted with concentrated hydrochloric acid. The pH was adjusted to 3 by addition of water. The precipitated solid was filtered and dried.

[0408] 1H-NMR(300 Mhz, D6-DMSO) δ ppm: 8.57 (s, 1H), 8.54 (s, 1H), 8.28 (d, 1H), 8.02 (d, 1H). The -COOH protons do not appear in the measured spectrum.

[0409] 7-Bromo-4-hydroxyisoquinoline-3-carboxylate ethyl ester [ka]

[0410] 22.0 g (45.5 mmol) of 4-bromo-2-[[(2-ethoxy-2-oxo ethyl)-(p-tolylsulfonyl)amino]methyl]benzoate methyl and 9.80g (182.2 mmol) NaOEt was dissolved in 50 ml of ethanol and left at room temperature for 16 hours. The reaction mixture was then adjusted to pH 7 by adding concentrated hydrochloric acid. The precipitated solid was separated by filtration. The crude product was further transformed without further purification. Ta.

[0411] 1 H-NMR(300 Mhz, D6-DMSO) δ ppm: 11.72 (br, 1H), 8.86 (s, 1H), 8.49 (d, 1H), 8.2 3 (d, 1H), 8.03 - 8.00 (m, 1H), 4.46 (q, 2H), 1.39 (t, 3H). 4-Bromo-2-[[(2-ethoxy-2-oxoethyl)-(p-tolylsulfonyl) )amino]methyl]benzoic acid methyl ester [ka]

[0412] 17.0 g (55.6 mmol) of methyl 4-bromo-2-(bromomethyl)benzoate A mixture of 11.5 g (83.3 mmol) of potassium carbonate was suspended in 50 ml of DMF. The mixture was stirred at room temperature for 20 minutes. Ethyl (arylsulfonylamino)acetate was added, and the resulting reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched by the addition of 100 ml of water, and the mixture was then diluted with 150 ml of acetic acid. The combined organic phases were washed with 100 ml of saturated sodium chloride solution. The mixture was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography. The mixture was purified by filtration (mobile phase: pentane / ethyl acetate = 8 / 1).

[0413] 1 H-NMR(300 Mhz, D6-DMSO) δ ppm: 7.77 - 7.60 (m, 5), 7.43 (d, 2H), 4.74 (s, 2H), 4.06 (s, 2H), 3.98 (q, 2H), 3.80 (s, 3H), 2.41 (s, 3H), 1.10 (t, 3H). 4-Hydroxy-3-[3-methyl-6-(trifluoromethyl)imidazo[4,5- b]pyridin-2-yl]isoquinoline-7-carbonitrile [ka]

[0414] 1.60 g (0.789 mmol, 10% strength) of t-Bu3-P and 59 mg (0 0.26 mmol) of Pd(OAc)2 in 10 ml of N-methyl-2-pyrrolidone 0 mg (1.32 mmol) of 7-chloro-3-[3-methyl-6-(trifluoromethyl) 1,2-diyl)imidazo[4,5-b]pyridin-2-yl]isoquinolin-4-ol and 27 9 mg (0.66 mmol) of K4[Fe(CN)6] 3H2O was added to the solution. The mixture was stirred at 140°C under a nitrogen atmosphere for 16 hours. The reaction was then diluted with 100 ml of water. The mixture was quenched by addition of 150 ml of ethyl acetate twice. The phase was washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The product was purified by preparative high performance liquid chromatography (MeCN / H2O).

[0415] 1 H-NMR(300 Mhz, D6-DMSO) δ ppm: 14.58 (br, 1H), 9.09 (s, 1H), 8.86 - 8.83 (m, 2 H), 8.70 (s, 1H), 8.48 (d, 1H), 8.13 (d, 1H), 4.46 (s, 3H). 4-Ethylsulfanyl-3-[3-methyl-6-(trifluoromethyl)imidazo[ 4,5-b]pyridin-2-yl]-7-(2,2,2-trifluoroethylsulfani Isoquinoline [ka]

[0416] While stirring, 149 mg (1.28 mmol) of 2,2,2-trifluoromethane- 1-thiol, 144 mg (1.28 mmol) of t-BuOK, 122 mg (0.64 182 mg (1.28 mmol) of N1,N2-dimethylcyclohexane 300 mg (0.64 mmol) of hexane-1,2-diamine in 10 ml of DMF ) of 7-bromo-4-ethylsulfanyl-3-[3-methyl-6-(trifluoroethyl) The reaction mixture was added to a solution of 4,5-b-imidazo[4,5-b]pyridin-2-yl]isoquinoline. The mixture was heated in a microwave at 140°C for 2 hours and then diluted with 100 ml of water. The mixture was extracted twice with 150 ml of ethyl acetate, and the organic phase was washed with saturated sodium chloride. The residue was washed with aqueous thorium dioxide, dried over sodium sulfate, filtered, and concentrated. The mixture was purified by column chromatography (pentane / ethyl acetate=8 / 1).

[0417] 1 H-NMR(300 Mhz, D6-DMSO) δ ppm: 9.44 (s, 1H), 8.87 (d, 1H), 8.65 (d, 1H), 8.57 (d, 1H), 8.49 (d, 1H), 8.13 (dd, 1H), 4.35 (q, 2H), 3.77 (s, 3H), 2.84 (q, 2H), 0.98 (t, 3H). 7-Cyclopropyl-4-ethylsulfanyl-3-[3-methyl-6-(trifluoromethyl) (trimethyl)imidazo[4,5-b]pyridin-2-yl]isoquinoline [ka]

[0418] While stirring, 276 mg (3.21 mmol) of cyclopropylboronic acid, 74 mg (0.06 mmol) Pd(PPh3)4 and 314 mg (0.96 mmol) C s2CO3 was dissolved in 300 mg (0.64 mmol) of 7-bromo-4 -ethylsulfanyl-3-[3-methyl-6-(trifluoroethyl)imidazo[4, The reaction mixture was heated at 85° C. for 1 hour. The mixture was stirred for 6 hours and then quenched by the addition of 100 ml of water. The organic phase was extracted twice with 50 ml of saturated aqueous sodium chloride solution and then washed with sodium sulfate. The residue was purified by preparative thin layer chromatography (silica gel) (pentachloroethylene). The mixture was purified by a solvent mixture of ethanol / ethyl acetate (8 / 1).

[0419] LC-MS: Rt (min): 1.37; MS: (M+H + ): 429. N-[4-ethylsulfanyl-3-[3-methyl-6-(trifluoromethyl)imine Dazo[4,5-b]pyridin-2-yl]-7-isoquinolyl]carbamic acid methyl ester [ka]

[0420] While stirring, add 96 mg (1.28 mmol) of methyl carbamate, 67 mg (0. 0.6 mmol) of Pd2(dba) 3· CHCl3, 74 mg (0.13 mmol) Santophos and 419 mg (1.28 mmol) of Cs2CO3 were added to 10 ml of 1, 200 mg (0.43 mmol) of 7-bromo-4-ethylsulfa in 4-dioxane Nyl-3-[3-methyl-6-(trifluoroethyl)imidazo[4,5-b]pyridine The reaction mixture was stirred at 110° C. for 16 hours. The mixture was then quenched by the addition of 100 ml of water. The organic phase was extracted twice, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and filtered. The residue was purified by silica gel column chromatography (mobile phase: pentane / ethyl acetate). The mixture was purified by filtration (C1 / C2=8 / 1).

[0421] 1 H-NMR(400 Mhz, D6-DMSO) δ ppm: 10.36 (br, 1H), 9.40 (s, 1H), 8.86 (d, 1H), 8.6 4 (d, 1H), 8.55 (d, 1H), 8.48 (d, 1H), 8.02 (dd, 1H), 3.77 (s, 3H), 3.76 (s, 3H) , 2.81 (q, 2H), 0.97 (t, 3H). 4,7-bis(ethylsulfanyl)-3-[3-methyl-6-(trifluoromethyl) )Imidazo[4,5-b]pyridin-2-yl]isoquinoline [ka]

[0422] 670 mg (10.8 mmol) EtSH, 170 mg (0.16 mmol) Pd 2(dba) 3· CHCl3, 190 mg (0.32 mmol) of xanthophos and 420 mg (3.25 mmol) of Hunig's base in 15 ml of 1,4-dioxane 600 mg (1.10 mmol) of [7-bromo-3-[3-methyl-6-(trifluoromethyl)methyl]propanol] (4,5-b)imidazo[4,5-b]pyridin-2-yl]-4-isoquinolyl]trifluoromethyl The reaction mixture was stirred at 80°C for 16 hours. The mixture was then quenched by the addition of 100 ml of water and ethyl acetate (2 x 150 ml The organic phase was washed with saturated aqueous NaCl, dried over sodium sulfate, and filtered. The crude product was purified by silica gel column chromatography (Penn The mixture was purified by hexane / ethyl acetate (8:1).

[0423] 1 H-NMR(400 Mhz, D6-DMSO) δ ppm: 9.43 (s, 1H), 8.87 (d, 1H), 8.66 (d, 1H), 8.51 (d, 1H), 8.21 (d, 1H), 7.94 (dd, 1H), 3.77 (s, 3H), 3.24 (q, 2H), 2.83 (q, 2H), 1.38 (t, 3H), 0.98 (t, 3H). 4,7-bis(ethylsulfonyl)-3-[3-methyl-6-(trifluoromethyl) Imidazo[4,5-b]pyridin-2-yl]isoquinoline (I-34) [ka]

[0424] 0.10 g (2.23 mmol) formic acid and 0.35 g (3.11 mmol, 30% strength) hydrogen peroxide in 0.20 g (0.44 mmol) of dichloromethane in 10 ml of dichloromethane. 4,7-bis(ethylsulfanyl)-3-[3-methyl-6-(trifluoromethyl) ) was added to a solution of imidazo[4,5-b]pyridin-2-yl]isoquinoline. The mixture was stirred at room temperature for 6 hours, then diluted with an aqueous solution of Na2S2O3 and added to 30 ml of dichloromethane. The organic phase was dried over sodium sulfate, filtered and rotary evaporated. The residue was purified by preparative HPLC (mobile phase: MeCN / H2O).

[0425] Analytical data: See peak list Analogously to the examples and according to the above preparation methods, the following compounds of formula (I) can be obtained: You can: [Table 1-1]

[0426] [Table 1-2]

[0427] [Table 1-3]

[0428] [Table 1-4]

[0429] [Table 1-5]

[0430] [Table 1-6]

[0431] 1 Further details of the 1 H NMR peak list are available from the Research Disclosure Database. This can be found under patent number 564025. [Table 2-1]

[0432] [Table 2-2]

[0433] [Table 2-3]

[0434] [Table 2-4]

[0435] [Table 2-5]

[0436] [Table 2-6]

[0437] [Table 2-7]

[0438] [Table 2-8]

[0439] [Table 2-9]

[0440] [Table 2-10]

[0441] [Table 2-11]

[0442] [Table 2-12]

[0443] Usage example Cat flea (Ctenocephalides felis) - Infection with adult cat fleas In vitro contact test To coat the test tubes, 9 mg of active compound was first added to 1 mL of acetone. Dissolve in PA and then dilute with acetone PA to the desired concentration. - By rotating and rocking on a vital shaker (rocking rotation 30 rpm for 2 hours) 250 μL of the solution was evenly distributed on the inner wall and bottom of a 25 mL glass tube. ppm active ingredient solution and 44.7 cm 2 If we assume that the inner surface of the 5 μg / cm 2 An area-based dose of is achieved.

[0444] After the solvent was evaporated, 5-10 adult cat fleas (Ctenocephalids) were added to the tube. The container is then sealed with a plastic lid with holes and stored at room temperature. Incubate in a horizontal position at room temperature and ambient humidity. After 48 hours, determine potency. For this purpose, the tube is held upright and tapped to cause the cat fleas to fall to the bottom of the test tube. Cat fleas that remain motionless or move jerkily at the bottom of the tube are dead. are believed to be either dead or dying.

[0445] A substance is tested at 5 μg / cm 2 Achieve at least 80% efficacy at application rates of If so, the substance will be effective against cat fleas (Ctenocephalides felis). 100% efficacy means that all cat fleas are dead or dying. 0% efficacy means that no cat fleas were damaged.

[0446] In this test, for example, the following compound from the preparation examples was 2 (=50 0g / ha) shows 100% efficacy: I-005, I-025, I-032 , I-034, I-037.

[0447] In this test, for example, the following compound of the Preparation Examples was tested at 5 μg / cm 2 (=500g / ha) and shows 90% efficacy: I-012.

[0448] Brown dog tick (Rhipicephalus sanguineus) - adult In vitro contact test using Rhipicephalus sanguineus To coat the test tubes, 9 mg of active compound was first added to 1 mL of acetone. Dissolve in PA and then dilute with acetone PA to the desired concentration. - By rotating and rocking on a vital shaker (rocking rotation 30 rpm for 2 hours) Distribute 250 μL of the solution evenly over the inner wall and bottom of a 25 mL test tube. pm of active ingredient solution and 44.7 cm 2 If we assume that the inner surface of the μg / cm 2 An area-based dose of is achieved.

[0449] After the solvent was evaporated, 5 to 10 adult Rhipicephalus sanguineus were added to the tube. phalus sanguineus) and made of plastic with holes Seal with the lid and incubate in a horizontal position in the dark at room temperature and ambient humidity for 48 hours. After a period of time, the effectiveness is sought. For this purpose, tapping is performed on the brown dog ticks. The ink was then dropped onto the bottom of the tube and heated to 45-50°C on a hot plate for no longer than 5 minutes. The heat is intended to be absorbed by remaining motionless on the floor of the tube or by crawling up. The Brown Dog Tick has jerky movements that make it difficult to avoid. Presumed to be dead or dying.

[0450] A substance is tested at 5 μg / cm 2 Achieve at least 80% efficacy at application rates of If so, the substance is likely to infect the brown dog tick (Rhipicephalus sanguineus). 100% efficacy is equivalent to 100% efficacy against all brown dog species. 0% efficacy means that the mites are dead or dying. This means there were no loco ticks.

[0451] In this test, for example, the following compound of the Preparation Examples was tested at 5 μg / cm 2 (=500g / ha), showing 100% efficacy: I-032, I-037.

[0452] Boophilus microplus - injection test Solvent: Dimethyl sulfoxide To prepare a suitable active compound formulation, 10 mg of active compound is added to 0.5 ml of solution. The concentrate is mixed with the solvent and diluted with the solvent to the desired concentration.

[0453] Five engorged adult female cow ticks (Boophilus microplus) The animal is then transferred to a dish and maintained in a climate chamber. do.

[0454] Efficacy is assessed after 7 days by the laying of fertilized eggs. The eggs are kept in a climate chamber until the larvae hatch after approximately 42 days. 0% means that no ticks laid fertilized eggs; 0% means that all eggs were fertilized. means.

[0455] In this test, for example, the following compound from the Preparation Examples was administered at 20 μg per animal: 80% efficacy at an application rate of: I-010.

[0456] Cat flea (Ctenocephalides felis) - oral test Solvent: Dimethyl sulfoxide To prepare a suitable active compound formulation, 10 mg of active compound is added to 0.5 ml of distilled water. Mix with methyl sulfoxide and dilute with citrated bovine blood to the desired concentration. The degree.

[0457] Approximately 20 unfed rats were placed in a chamber whose top and bottom were closed with gauze. Put adult cat fleas (Ctenocephalides felis) in the container. A metal cylinder closed with a film is placed on top of the chamber. It contains a combination of active compounds, which are ingested by cat fleas through a parafilm membrane. It can be taken.

[0458] After two days, calculate the insecticidal rate (%). 100% means that all cat fleas have died. 0% means that no cat fleas were killed; 0% means that no cat fleas were killed.

[0459] In this test, for example, the following compounds from the preparation examples were used at an application rate of 100 ppm: , showing 100% efficacy: I-005, I-008, I-010, I-012, I-01 3, I-025, I-034, I-037.

[0460] In this test, for example, the following compounds from the preparation examples were used at an application rate of 100 ppm: , showing 80% efficacy: I-003, I-024.

[0461] Sheep blowfly (Lucilia cuprina) test Solvent: Dimethyl sulfoxide To prepare a suitable active compound formulation, 10 mg of active compound is added to 0.5 ml of distilled water. Mix with methyl sulfoxide and dilute the concentrate with water to the desired concentration.

[0462] Approximately 20 Australian sheep blowflies ( L1 larvae of the fungus Lucilia cuprina were incubated in ground horse meat and the desired concentration of the active compound. The mixture is transferred into a test vessel containing the formulation.

[0463] After two days, calculate the insecticidal rate (%). 100% means that all the sheep blowfly larvae are dead. 0% means that no sheep blowfly larvae were killed; 0% means that no sheep blowfly larvae were killed.

[0464] In this test, for example, the following compounds from the preparation examples were used at an application rate of 100 ppm: , showing 100% efficacy: I-010, I-034.

[0465] Diabrotica balteata - spray test Solvent: 78.0 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve in a solvent and add emulsifier at a concentration of 1000 ppm until the desired concentration is achieved. Further test concentrations are prepared by mixing the formulation with water containing an emulsifier. Obtained by dilution with water.

[0466] Pre-swollen wheat (Triticum aestivum) grains are mixed with agar and a small amount of water. Incubate for 1 day in a filled multiwell plate (1 well per well) The germinated wheat grains are sprayed with the active compound preparation at the desired concentration. At least 10-20 Diabrotica balteatus a) The larvae are parasitized.

[0467] After 7 days, the efficacy (%) is calculated. 100% is the percentage when all wheat plants are untreated. 0% means that no wheat plants grew; This means that

[0468] In this test, for example, the following compounds from the preparation examples were applied at 160 μg / well: The amounts showing 100% efficacy are: I-004, I-006, I-016, I-018, I- 019, I-020, I-025, I-027, I-029, I-030, I-031, I-039, I-041, I-042, I-043, I-044, I-045, I-04 6, I-048, I-050, I-051, I-052, I-053.

[0469] In this test, for example, the following compounds from the preparation examples were applied at 160 μg / well: The doses showing 80% efficacy are: I-005, I-028, I-049.

[0470] Sweet potato root-knot nematode (Meloidogyne incognita) test Solvent: 125.0 parts by weight acetone To prepare a suitable active compound formulation, 1 part by weight of the active compound is added to the specified amount of solvent. and dilute the concentrate with water to the desired concentration.

[0471] In a container, add sand, the active compound solution, and the sweet potato root-knot nematode (Meloidogyne incognita) egg / larvae suspension, and lettuce seeds. The seed germinates and the plant develops. Galls develop on the roots.

[0472] After 14 days, nematicidal efficacy (%) is determined by gall formation. 100% is when no galls are visible. 0% means that the number of galls on the treated plants was significantly lower than that on the untreated control. This means responding to

[0473] In this test, for example, the following compounds from the preparation examples were used at a rate of 20 ppm: 00% efficacy: I-008, I-027, I-041.

[0474] In this test, for example, the following compounds from the preparation examples showed a 9% efficacy at an application rate of 20 ppm: Showing 0% efficacy: I-004, I-005, I-006, I-020, I-026, I -042.

[0475] Green peach aphid (Myzus persicae) - oral test Solvent: 100 parts by weight acetone To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve in a solvent and mix with water to the desired concentration.

[0476] 50 μl of the active compound preparation was transferred into a microtiter plate and 150 μl Bring to a final volume of 200 μl with IPL41 insect medium (33% + 15% sugar). The plate was sealed with parafilm and the peach squid in the second microtiter plate was placed on the plate. A mixed population of aphids (Myzus persicae) punctured the Parafilm. The solution can then be inhaled.

[0477] After 5 days, calculate the efficacy (%). 100% means that all the green peach aphids have died. 0% means that no green peach aphids were killed; 0% means that no green peach aphids were killed.

[0478] In this test, for example, the following compound from the preparation example showed 1 Showing 00% efficacy: I-001, I-002, I-003, I-004, I-005, I-007, I-008, I-010, I-012, I-013, I-015, I-01 6, I-018, I-019, I-020, I-021, I-022, I-024, I- 025, I-027, I-028, I-029, I-030, I-031, I-032, I-033, I-034, I-035, I-036, I-037, I-038, I-03 9, I-041, I-042, I-043, I-044, I-045, I-046, I- 051, I-052.

[0479] In this test, for example, the following compound from the preparation example showed a 9 ppm application rate: Showing 0% efficacy: I-006, I-014, I-026, I-050.

[0480] Green peach aphid (Myzus persicae) - spray test Solvent: 78 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve in a solvent and mix with water containing an emulsifier at a concentration of 1000 ppm. To obtain further test concentrations, the formulation was diluted with water containing an emulsifier. Dilute with.

[0481] All stages of the green peach aphid (Myzus persicae) are present. The desired concentration of 100mg of ethanol was applied to the leaf disks of Chinese cabbage (Brassica pekinensis) The active ingredient combination is sprayed.

[0482] After 5 days, calculate the efficacy (%). 100% means that all the green peach aphids have died. 0% means that no green peach aphids were killed; 0% means that no green peach aphids were killed.

[0483] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and show 100% efficacy: I-006, I-010, I-013, I-014, I-0 18, I-026, I-032, I-037, I-042, I-045.

[0484] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and show 90% efficacy: I-001, I-002, I-003, I-012, I-02 0, I-024, I-025, I-028, I-029, I-034, I-035, I- 041, I-043, I-044.

[0485] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and shows 70% efficacy: I-027.

[0486] Mustard beetle (Phaedon cochleariae) - spray test Solvent: 78.0 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve in a solvent and mix with water containing an emulsifier at a concentration of 1000 ppm. To obtain further test concentrations, the formulation was diluted with water containing an emulsifier. Dilute with.

[0487] The desired concentration of chlorella was applied to the leaf disks of Chinese cabbage (Brassica pekinensis). The active compound formulation was sprayed and, after drying, the mustard beetles were e) Parasitize the larvae of (Phaedon cochleariae).

[0488] After 7 days, calculate the efficacy (%). 100% means that all mustard beetle larvae are dead. 0% means that no mustard beetle larvae were killed; 0% means that no mustard beetle larvae were killed. do.

[0489] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and show 100% efficacy: I-001, I-002, I-007, I-008, I-0 10, I-012, I-013, I-014, I-021, I-022, I-024, I -026, I-032, I-035, I-037, I-038.

[0490] Fall armyworm (Spodoptera frugiperda) - spray test Solvent: 78.0 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve in a solvent and mix with water containing an emulsifier at a concentration of 1000 ppm. To obtain further test concentrations, the formulation was diluted with water containing an emulsifier. Dilute with.

[0491] The desired concentration of the active compound formulation was applied to corn (Zea mays) leaf discs. After spraying and drying, the armyworm (Spodoptera f rugiperda) larvae.

[0492] After 7 days, calculate the efficacy (%). 100% means that all the armyworm larvae are dead. 0% means that no armyworm larvae were killed; 0% means that no armyworm larvae were killed. do.

[0493] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and show 100% efficacy: I-001, I-004, I-005, I-006, I-0 08, I-010, I-012, I-013, I-014, I-016, I-019, I -020, I-021, I-022, I-024, I-025, I-026, I-027 , I-028, I-029, I-030, I-031, I-032, I-033, I-0 36, I-037, I-038, I-039, I-041, I-043, I-045, I -046, I-048, I-049, I-050, I-051, I-052, I-053 .

[0494] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and showing 83% efficacy: I-015, I-034, I-042.

[0495] In this test, for example, the following compounds from the preparation examples were applied at a rate of 100 g / ha: and shows 67% efficacy: I-007.

[0496] Comparative Example Green peach aphid (Myzus persicae) - spray test (MYZUPE) Solvent: 78.0 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound preparation, 1 part by weight of active compound is added to the stated weight 1 part solvent and add 1000 ppm emulsifier concentration until desired concentration is reached. To obtain further test concentrations, the formulation is diluted with water containing an emulsifier. do.

[0497] All stages of the green peach aphid (Myzus persicae) are present. The desired concentration of 100mg of ethanol was applied to the leaf disks of Chinese cabbage (Brassica pekinensis) of the active compound preparation is sprayed.

[0498] After the desired period, the efficacy (%) is measured, with 100% meaning that all aphids have been killed. 0% means that no aphids were killed.

[0499] In this test, for example, the following compounds from the preparation examples showed superior efficacy over the prior art: Refer to Table 1.

[0500] Fall armyworm (Spodoptera frugiperda) - spray test (S PODFR) Solvent: 78.0 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound preparation, 1 part by weight of active compound is added to the stated weight 1 part solvent and add 1000 ppm emulsifier concentration until desired concentration is reached. To obtain further test concentrations, the formulation is diluted with water containing an emulsifier. do.

[0501] The desired concentration of the active compound formulation is applied to corn (Zea mays) leaf discs. After drying, the leaves of the armyworm (Spodoptera frugiperda ) larvae (caterpillars).

[0502] After the desired period, the efficacy (%) is measured; 100% means that all larvae have died. , 0% means that no larvae died.

[0503] In this test, for example, the following compounds from the preparation examples were found to be superior to the prior art: Show efficacy: See Table 1.

[0504] Green peach aphid (Myzus persicae) - spray test (MYZUPE S ) Solvent: 14 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the stated parts by weight of and an emulsifier concentration of 1000 ppm was added until the desired concentration was reached. To obtain further test concentrations, the formulation is diluted with water containing an emulsifier. If ammonium salt and / or penetrant are required, add 1000pp each. It is added to the formulation solution at a concentration of m.

[0505] Bell peppers heavily infested with green peach aphids (Myzus persicae) The plants (Capsicum annuum) are sprayed with the active compound formulation at the desired concentration. This is how it is handled.

[0506] After the desired period, the efficacy (%) is measured, with 100% meaning that all aphids have been killed. 0% means that no aphids were killed.

[0507] In this test, for example, the following compounds from the preparation examples were found to be superior to the prior art: Show efficacy: See Table 1.

[0508] Peach aphid (Myzus persicae) - Irrigation test (MYZUPE D ) Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable active compound preparation, 1 part by weight of active compound is mixed with the above-mentioned amounts of solvent and The concentrate is mixed with an emulsifier and diluted with water to the desired concentration, at which point irrigation is performed. The volume of soil to be treated must be taken into consideration. The emulsifier concentration in the soil must not exceed 40 ppm. To obtain further test concentrations, dilutions should be made using water.

[0509] All developmental stages of the green peach aphid (Myzus persicae) in pots containing soil icae) on Savoy cabbage (Brassica oleracea) The water supply is provided with the active compound preparation at the desired concentration.

[0510] After the desired period, efficacy (%) is determined; 100% means that all green peach aphids have been killed. 0% means that no green peach aphids were killed; 0% means that no green peach aphids were killed.

[0511] In this test, for example, the following compounds from the preparation examples showed superior efficacy over the prior art: Shown are the forces: see Table 1.

[0512] Cotton aphid (Aphis gossypii) - spray test (APHIGO) Solvent: 14 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable active compound preparation, 1 part by weight of the active compound is added to the above-mentioned parts by weight of the solvent. Dissolve in a solvent and add emulsifier at a concentration of 1000 ppm until the desired concentration is achieved. To obtain further test concentrations, the formulation is formulated with water containing an emulsifier. If necessary, add ammonium salts and / or penetrants. Both of them are added to the formulation solution at a concentration of 1000 ppm.

[0513] Cotton plants (G) heavily infested with cotton aphids (Aphis gossypii) ossypium hirsutum) are sprayed with the active compound formulation at the desired concentration.

[0514] After the desired period has elapsed, the insecticidal rate (%) is calculated. 100% means that all cotton aphids are killed. 0% means that no cotton aphids were killed; 0% means that no cotton aphids were killed.

[0515] In this test, for example, the following compounds from the preparation examples were found to be superior to the prior art. The efficacy of the compounds is shown in Table 1.

[0516] Fall armyworm (Spodoptera frugiperda) - spray test (S PODFR S) Solvent: 14 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the stated weight fraction. The solution is dissolved using a quantity of solvent and emulsifier and then mixed with water until the desired concentration is reached. To obtain further test concentrations, water is used for dilution. Ammonium salts or / If the addition of a penetrating agent (rapeseed oil methyl ester) is required, the finished compound solution must be diluted. After being cooled, they are pipetted in at a concentration of 1000 ppm each.

[0517] Corn plants (Zea mays) are sprayed with the active compound formulation at the desired concentration, After 5, 12 and 19 days, the number of Spodoptera The specimen was infested with five caterpillars (L2) of F. frugiperda. Can.

[0518] The mortality rate (%) was measured 6 days after infection. 100% means that all larvae were killed. , 0% means that no larvae died.

[0519] In this test, for example, the following compounds from the preparation examples show good efficacy: See 2.

[0520] Heliothis armigera test (HELIAR S) Solvent: 14 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve with solvent and emulsifier and blend with water until desired concentration is reached. Water is used for dilution to obtain the test concentration. If the addition of a penetrant (rapeseed oil methyl ester) is required, the finished compound solution is diluted. They are then pipetted into the container at a concentration of 1000 ppm each.

[0521] The desired concentration of the active compound formulation is applied to cotton plants (Gossypium hirsutum). and 12 and 19 days later, the cotton bollworm (Heliothis a The specimens were infested with five L2 larvae of the fungus, L. rmigera.

[0522] The insecticidal rate (%) was calculated 6 days after infection. 100% means that all cotton bollworm larvae were dead. 0% means that no bollworms died; 0% means that no bollworms died.

[0523] In this test, for example, the following compounds of the Preparation Examples show good efficacy: I want to be illuminated.

[0524] Diamondback moth (Plutella xylostella) test (PLUTMA S) Solvent: 14 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve with solvent and emulsifier and blend with water until desired concentration is reached. Water is used for dilution to obtain the test concentration. If the addition of a penetrant (rapeseed oil methyl ester) is required, the finished compound solution is diluted. They are then pipetted into the container at a concentration of 1000 ppm each.

[0525] On cabbage plants (Brassica oleracea var. sabauda) The desired concentration of the active compound formulation was sprayed on the rice. After 19 days, the rice was treated with the diamondback moth (Plutella xylostella). The specimens were infested with 10 L2 larvae of B. japonica (B. japonica).

[0526] The insecticidal rate (%) was calculated 6 days after infection. 100% means that all the diamondback moth larvae were dead. 0% means that no diamondback moth larvae died.

[0527] In this test, for example, the following compounds from the preparation examples show good efficacy: Table 2 Please refer to.

[0528] Mustard beetle (Phaedon cochleariae) test (PHAECO S) Solvent: 14 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable active compound formulation, 1 part by weight of active compound is added to the above-mentioned parts by weight of solvent. Dissolve with solvent and emulsifier and blend with water until desired concentration is reached. Water is used for dilution to obtain the test concentration. If the addition of a penetrant (rapeseed oil methyl ester) is required, the finished compound solution is diluted. They are then pipetted into the container at a concentration of 1000 ppm each.

[0529] On cabbage plants (Brassica oleracea var. sabauda) The desired concentration of the active compound formulation is sprayed on the mustard beetles. Parasitize 10 L2 larvae of Phaedon cochleariae .

[0530] After the desired period, the kill rate (%) is calculated. 100% means that all larvae have died. ; 0% means that no larvae died.

[0531] In this test, for example, the following compounds from the preparation examples show good efficacy: Table 2 Please refer to. [Table 3] [Table 4]

Claims

1. Formula (I) 【Chemistry 1】 [During the ceremony, R １ (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ ) -cyanoalkyl, (C １ -C ６ )-hydroxyalkyl, (C １ -C ６ )-Alkoxy - (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkoxy-(C １ -C ６ ) - Al Kill, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkenyloxy-(C １ -C ６ )-alkyl, (C ２ -C ６ )-haloalkenyloxy-(C １ -C ６ )-alkyl, ( C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-cyanoalkenyl, (C ２ -C ６ ) - Alkynyl, (C ２ -C ６ )-alkynyloxy-(C １ -C ６ )-alkyl, (C ２ - C ６ )-haloalkynyloxy-(C １ -C ６ )-alkyl, (C ２ -C ６ ) - Haloal Quinyl, (C ２ -C ６ )-cyanoalkynyl, (C ３ -C ８ )-cycloalkyl, (C ３ -C ８ )-cycloalkyl-(C ３ -C ８ )-cycloalkyl, (C １ -C ６ ) -Archi Ru- (C ３ -C ８ )-cycloalkyl, halo-(C ３ -C ８ )-Cycloalkyl, amino , (C １ -C ６ )-alkylamino, di-(C １ -C ６ )-alkyl-amino, (C ３ - C ８ )-cycloalkylamino, (C １ -C ６ )-alkylcarbonylamino, (C １ - C ６ )-alkylthio-(C １ -C ６ )-alkyl, (C １ -C ６ )-Haloalkylthio - (C １ -C ６ )-alkyl, (C １ -C ６ )-Alkyl sulfinyl-(C １ -C ６ ) -alkyl, (C １ -C ６ )-haloalkylsulfinyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-Alkylsulfonyl-(C １ -C ６ )-alkyl, (C １ -C ６ ) - Ha 3-alkylsulfonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy-(C １ -C ６ )-alkylthio-(C １ -C ６ )-alkyl, (C １ -C ６ )-Alkoxy- (C １ -C ６ )-Alkyl sulfinyl-(C １ -C ６ )-alkyl, (C １ -C ６ ) - Alkoxy-(C １ -C ６ )-Alkylsulfonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-alkylcarbonyl-(C １ -C ６ )-alkyl, (C １ -C ６ ) - Haloal Kylcarbonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxycarbonyl- (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkoxycarbonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-Alkyl sulfonylamino, aminosulfonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-alkylaminosulfonyl-(C １ -C ６ )-a Rukill or Ji (C １ -C ６ )-alkylaminosulfonyl-(C １ -C ６ ) -Archi represents the R ａ , R ｂ , R ｃ , R ｄ are each independently hydrogen, cyano, halogen, nitro, acetonitrile, Chiral, hydroxy, amino, SCN, tri-(C １ -C ６ )-alkylsilyl, (C ３ - C ８ )-cycloalkyl, (C ３ -C ８ )-cycloalkyl-(C ３ -C ８ )-cycloa Rukill, (C １ -C ６ )-alkyl-(C ３ -C ８ )-cycloalkyl, halo-(C ３ - C ８ )-cycloalkyl, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-cyanoalkyl, (C １ -C ６ )-Hydroxyalkyl, hydroxyca Carbonyl-(C １ -C ６ )-alkoxy, (C １ -C ６ )-alkoxycarbonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ ) - Cyanoa Alkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ２ -C ６ )-cyanoalkynyl, (C １ -C ６ )-alkoxy, (C １ -C ６ ) - Haloalkoki C, (C １ -C ６ )-cyanoalkoxy, (C １ -C ６ )-alkoxycarbonyl-(C １ -C ６ )-alkoxy, (C １ -C ６ )-alkoxy-(C １ -C ６ )-alkoxy, (C １ -C ６ )-alkylhydroxyimino, (C １ -C ６ )-alkoxyimino, (C １ -C ６ )-alkyl-(C １ -C ６ )-alkoxyimino, (C １ -C ６ ) - Haloal Kill-(C １ -C ６ )-alkoxyimino, (C １ -C ６ )-alkylthio, (C １ -C ６ )-haloalkylthio, (C １ -C ６ )-alkoxy-(C １ -C ６ )-Alkylthio , (C １ -C ６ )-alkylthio-(C １ -C ６ )-alkyl, (C １ -C ６ ) -Archi Rusulfinyl, (C １ -C ６ )-haloalkylsulfinyl, (C １ -C ６ ) - Arco Kishi (C １ -C ６ )-alkylsulfinyl, (C １ -C ６ )-Alkyl sulfinyl - (C １ -C ６ )-alkyl, (C １ -C ６ )-alkylsulfonyl, (C １ -C ６ ) - Haloalkylsulfonyl, (C １ -C ６ )-alkoxy-(C １ -C ６ )-Alkyl Sulfate Honil, (C １ -C ６ )-Alkylsulfonyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-alkylsulfonyloxy, (C １ -C ６ )-alkylcarbonyl, (C １ -C ６ )-alkylthiocarbonyl, (C １ -C ６ )-haloalkylcarbonyl, (C １ -C ６ )-alkylcarbonyloxy, (C １ -C ６ )-alkoxycarbonyl, (C １ -C ６ )-haloalkoxycarbonyl, aminocarbonyl, (C １ -C ６ )-Alkylamino Carbonyl, (C １ -C ６ )-alkylaminothiocarbonyl, di-(C １ -C ６ ) - Al alkylaminocarbonyl, di-(C １ -C ６ )-alkylaminothiocarbonyl, (C ２ - C ６ )-alkenylaminocarbonyl, di-(C ２ -C ６ )-Alkenylaminocarbonyl Lu, (C ３ -C ８ )-cycloalkylaminocarbonyl, (C １ -C ６ )-Alkyl Sulfate phenylamino, (C １ -C ６ )-alkylamino, di-(C １ -C ６ )-Alkylamino , aminosulfonyl, (C １ -C ６ )-alkylaminosulfonyl, di-(C １ -C ６ ) -alkylaminosulfonyl, (C １ -C ６ )-Alkyl sulfoximino, aminothio Carbonyl, (C １ -C ６ )-alkylaminothiocarbonyl, di-(C １ -C ６ )-a alkyl-aminothiocarbonyl, (C ３ -C ８ )-cycloalkylamino, NHCO-( C １ -C ６ )-alkyl ((C １ -C ６ )-alkylcarbonylamino),NHCO- O (C １ -C ６ )-alkyl ((C １ -C ６ )-alkoxycarbonylamino) or NHCO-(C ３ -C ８ )-cycloalkyl ((C ３ -C ８ )-Cycloalkylcarbo nylamino), Here, the group R ａ , R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen; Q is a heteroaromatic 9- or 12-membered fused bicyclic or cyclic ring selected from the group consisting of Q1 to Q20; or a tricyclic ring system, 【Chemistry 2】 【change】 R ４ (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ ) - Cyanoalkyl, (C １ -C ６ )-hydroxyalkyl, (C １ -C ６ )-Alkoxy- (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkoxy-(C １ -C ６ ) -Archi ru, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkenyloxy-(C １ -C ６ ) -alkyl, (C ２ -C ６ )-haloalkenyloxy-(C １ -C ６ )-alkyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-cyanoalkenyl, (C ２ -C ６ )-a Rucynyl, (C ２ -C ６ )-alkynyloxy-(C １ -C ６ )-alkyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl Kill-(C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkyl-(C ３ -C ６ ) - Cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-Alkyl Oh (C １ -C ６ )-alkyl, (C １ -C ６ )-Alkyl sulfinyl-(C １ -C ６ )-alkyl, (C １ -C ６ )-Alkylsulfonyl-(C １ -C ６ )-alkyl or (C １ -C ６ )-alkylcarbonyl-(C １ -C ６ )-alkyl, R ５ , R ６ are each independently hydrogen, cyano, halogen, (C １ -C ６ )-Alkyl , (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ ) -Halo Alkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ - C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-cycloa Rukill, (C １ -C ６ )-alkyl-(C ３ -C ６ )-cycloalkyl, (C １ -C ６ ) -alkoxy, (C １ -C ６ )-haloalkoxy, (C １ -C ６ )-alkoxyimino, (C １ -C ６ )-alkylthio, (C １ -C ６ )-haloalkylthio, (C １ -C ６ ) - Alkylsulfinyl, (C １ -C ６ )-haloalkylsulfinyl, (C １ -C ６ ) - Alkylsulfonyl, (C １ -C ６ )-haloalkylsulfonyl, (C １ -C ６ ) - Al silylsulfonyloxy, (C １ -C ６ )-alkylcarbonyl, (C １ -C ６ ) - Helloa alkylcarbonyl, aminocarbonyl, (C １ -C ６ )-Alkylaminocarbonyl, di - (C １ -C ６ )-alkylaminocarbonyl, (C １ -C ６ )-Alkyl sulfonyl a Minho, (C １ -C ６ )-alkylamino, di-(C １ -C ６ )-Alkylamino, amino Sulfonyl, (C １ -C ６ )-alkylaminosulfonyl or di-(C １ -C ６ )-a represents alkylaminosulfonyl; n represents 0, 1 or 2; Here, if Q represents Q2, then R ｃ (C １ -C ６ )- does not represent haloalkyl. Compound.

2. In the formula, R １ However, (C １ -C ４ )-alkyl, (C １ -C ４ )-hydroxyalkyl, ( C １ -C ４ )-haloalkyl, (C １ -C ４ )-cyanoalkyl, (C １ -C ４ ) - Al Koxy (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkoxy-(C １ -C ４ ) -alkyl, (C ２ -C ４ )-alkenyl, (C ２ -C ４ )-alkenyloxy-(C １ -C ４ )-alkyl, (C ２ -C ４ )-haloalkenyloxy-(C １ -C ４ ) -Archi ru, (C ２ -C ４ )-haloalkenyl, (C ２ -C ４ )-cyanoalkenyl, (C ２ -C ４ )-alkynyl, (C ２ -C ４ )-alkynyloxy-(C １ -C ４ )-alkyl, ( C ２ -C ４ )-haloalkynyloxy-(C １ -C ４ )-alkyl, (C ２ -C ４ ) - Ha Alkynyl, (C ２ -C ４ )-cyanoalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ ) - Alkyl-(C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-alkylamino, di-(C １ -C ４ )-alkylamino, (C ３ -C ６ )-cycloalkylamino, (C １ -C ４ )-alkylcarbonylamino, (C １ -C ４ )-alkylthio-(C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkylthio-( C １ -C ４ )-alkyl, (C １ -C ４ )-Alkyl sulfinyl-(C １ -C ４ )-a Rukill, (C １ -C ４ )-haloalkylsulfinyl-(C １ -C ４ )-alkyl, (C １ -C ４ )-Alkylsulfonyl-(C １ -C ４ )-alkyl, (C １ -C ４ ) -Archi arylcarbonyl-(C １ -C ４ )-alkyl, (C １ -C ４ )-Haloalkylcarbonyl- (C １ -C ４ )-alkyl or (C １ -C ４ )-alkylsulfonylamino, R ａ , R ｂ , R ｃ , R ｄ are independently hydrogen, cyano, halogen, nitro, acetonitrile, Chiral, hydroxy, amino, SCN, tri-(C １ -C ４ )-alkylsilyl, (C ３ - C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-cycloa Rukill, (C １ -C ４ )-alkyl-(C ３ -C ６ )-cycloalkyl, halo-(C ３ - C ６ )-cycloalkyl, (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkyl, (C １ -C ４ )-cyanoalkyl, (C １ -C ４ )-hydroxyalkyl, (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkyl, (C ２ -C ４ )-alkenyl, (C ２ -C ４ )-haloalkenyl, (C ２ -C ４ )-cyanoalkenyl, (C ２ -C ４ ) - Alkini ru, (C ２ -C ４ )-haloalkynyl, (C ２ -C ４ )-cyanoalkynyl, (C １ -C ４ )-alkoxy, (C １ -C ４ )-haloalkoxy, (C １ -C ４ )-Cyanoalkoxy C, (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkoxy, (C １ -C ４ ) - Al Kylhydroxyimino, (C １ -C ４ )-alkoxyimino, (C １ -C ４ )-Alkyl - (C １ -C ４ )-alkoxyimino, (C １ -C ４ )-haloalkyl-(C １ -C ４ ) -alkoxyimino, (C １ -C ４ )-alkylthio, (C １ -C ４ )-Haloalkylthio O, (C １ -C ４ )-alkylthio-(C １ -C ４ )-alkyl, (C １ -C ４ ) - Al Kyrsulfinyl, (C １ -C ４ )-haloalkylsulfinyl, (C １ -C ４ ) - Al Kyrsulfinyl-(C １ -C ４ )-alkyl, (C １ -C ４ )-alkylsulfonyl, (C １ -C ４ )-haloalkylsulfonyl, (C １ -C ４ )-Alkylsulfonyl-(C １ -C ４ )-alkyl, (C １ -C ４ )-alkylsulfonyloxy, (C １ -C ４ ) - Alkylcarbonyl, (C １ -C ４ )-Haloalkylcarbonyl, aminocarbonyl, a Aminothiocarbonyl, (C １ -C ４ )-alkylaminocarbonyl, di-(C １ -C ４ ) -alkyl-aminocarbonyl, (C １ -C ４ )-alkylsulfonylamino, (C １ - C ４ )-alkylamino, di-(C １ -C ４ )-Alkylamino, aminosulfonyl, ( C １ -C ４ )-alkylaminosulfonyl, di-(C １ -C ４ )-Alkylaminosulfonate Nyl, aminothiocarbonyl, NHCO-(C １ -C ４ )-alkyl ((C １ -C ４ ) -alkylcarbonylamino), NHCO-O(C １ -C ４ )-alkyl ((C １ -C ４ )-alkoxycarbonylamino) or NHCO-(C ３ -C ６ )-Cycloalkyl ((C ３ -C ６ )-cycloalkylcarbonylamino), Here, the group R ａ , R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen; Q represents a heteroaromatic 9-membered fused bicyclic ring system selected from the group consisting of Q2, Q3, and Q16; death, 【Chemistry 3】 R ４ However, (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkyl, (C １ -C ４ ) -cyanoalkyl, (C １ -C ４ )-hydroxyalkyl, (C １ -C ４ )-Alkoxy - (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkoxy-(C １ -C ４ ) - Al Kill, (C ２ -C ４ )-alkenyl, (C ２ -C ４ )-alkenyloxy-(C １ -C ４ )-alkyl, (C ２ -C ４ )-haloalkenyloxy-(C １ -C ４ )-alkyl, ( C ２ -C ４ )-haloalkenyl, (C ２ -C ４ )-cyanoalkenyl, (C ２ -C ４ ) - Alkynyl, (C ２ -C ４ )-alkynyloxy-(C １ -C ４ )-alkyl, (C ２ - C ４ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloa Rukill - (C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-alkyl-(C ３ -C ６ ) -cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-Alkyl Thio-(C １ -C ４ )-alkyl, (C １ -C ４ )-Alkyl sulfinyl-(C １ -C ４ )-alkyl, (C １ -C ４ )-Alkylsulfonyl-(C １ -C ４ )-Alkyl or (C １ -C ４ )-alkylcarbonyl-(C １ -C ４ )-alkyl, R ５ , R ６ are each independently hydrogen, cyano, halogen, (C １ -C ４ )-Alkyl , (C １ -C ４ )-haloalkyl, (C ２ -C ４ )-alkenyl, (C ２ -C ４ ) -Halo Alkenyl, (C ２ -C ４ )-alkynyl, (C ２ -C ４ )-haloalkynyl, (C ３ - C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-cycloa Rukill, (C １ -C ４ )-alkyl-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ ) -alkoxy, (C １ -C ４ )-haloalkoxy, (C １ -C ４ )-alkoxyimino, (C １ -C ４ )-alkylthio, (C １ -C ４ )-haloalkylthio, (C １ -C ４ ) - Alkylsulfinyl, (C １ -C ４ )-haloalkylsulfinyl, (C １ -C ４ ) - Alkylsulfonyl, (C １ -C ４ )-haloalkylsulfonyl, (C １ -C ４ ) - Al silylsulfonyloxy, (C １ -C ４ )-alkylcarbonyl, (C １ -C ４ ) - Helloa alkylcarbonyl, aminocarbonyl, (C １ -C ４ )-Alkylaminocarbonyl, di - (C １ -C ４ )-alkylaminocarbonyl, (C １ -C ４ )-Alkyl sulfonyl a Minho, (C １ -C ４ )-alkylamino, di-(C １ -C ４ )-Alkylamino, amino Sulfonyl, (C １ -C ４ )-alkylaminosulfonyl or di-(C １ -C ４ )-a represents alkylaminosulfonyl; n represents 0, 1 or 2; Here, if Q represents Q2, then R ｃ (C １ -C ４ )-does not represent haloalkyl; A compound of formula (I) according to claim 1.

3. In the formula, R １ However, (C １ -C ４ )-alkyl, (C １ -C ４ )-hydroxyalkyl, ( C １ -C ４ )-haloalkyl, (C ２ -C ４ )-alkenyl, (C ２ -C ４ ) - Haloal Kenyl, (C ２ -C ４ )-alkynyl, (C ２ -C ４ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-alkylthio-(C １ -C ４ )-alkyl, (C １ -C ４ )-Alkyl sulfinyl-(C １ -C ４ )-alkyl or (C １ -C ４ ) - Alkylsulfonyl-(C １ -C ４ )-alkyl, R ａ , R ｂ , R ｃ , R ｄ are independently hydrogen, cyano, halogen, nitro, Roxy, Amino, SCN, Tri-(C １ -C ４ )-alkylsilyl, (C ３ -C ６ ) - C Chloroalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-cycloalkyl, ( C １ -C ４ )-alkyl-(C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ ) - C Chloroalkyl, (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkyl, (C １ -C ４ )-cyanoalkyl, (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkyl, (C ２ -C ４ )-alkenyl, (C ２ -C ４ )-haloalkenyl, (C ２ -C ４ ) - Cyanoa Alkenyl, (C ２ -C ４ )-alkynyl, (C ２ -C ４ )-haloalkynyl, (C ２ -C ４ )-cyanoalkynyl, (C １ -C ４ )-alkoxy, (C １ -C ４ ) - Haloalkoki C, (C １ -C ４ )-cyanoalkoxy, (C １ -C ４ )-alkylhydroxyimino, (C １ -C ４ )-alkoxyimino, (C １ -C ４ )-alkyl-(C １ -C ４ ) - Al Coximino, (C １ -C ４ )-alkylthio, (C １ -C ４ )-haloalkylthio, ( C １ -C ４ )-alkylsulfinyl, (C １ -C ４ )-haloalkylsulfinyl, ( C １ -C ４ )-alkylsulfonyl, (C １ -C ４ )-haloalkylsulfonyl, (C １ -C ４ )-alkylsulfonyloxy, (C １ -C ４ )-alkylcarbonyl, (C １ - C ４ )-haloalkylcarbonyl, aminocarbonyl, (C １ -C ４ )-Alkylamino Carbonyl, di-(C １ -C ４ )-alkylaminocarbonyl, (C １ -C ４ ) -Archi sulfonylamino, (C １ -C ４ )-alkylamino, di-(C １ -C ４ )-Alkyl Amino, aminosulfonyl, (C １ -C ４ )-alkylaminosulfonyl, di-(C １ - C ４ )-alkylaminosulfonyl, NHCO-(C １ -C ４ )-alkyl ((C １ - C ４ )-alkylcarbonylamino), NHCO-O-(C １ -C ４ )-Alkyl (( C １ -C ４ )-alkoxycarbonylamino) or NHCO-(C ３ -C ６ )-Cyclo Alkyl ((C ３ -C ６ )-cycloalkylcarbonylamino), Here, the group R ａ , R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen; Q is a heteroaromatic 9- or 12-membered condensed ring selected from the group consisting of Q2, Q3 and Q16; represents a fused bicyclic or tricyclic ring system, R ４ However, (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkyl, (C １ -C ４ ) -cyanoalkyl, (C １ -C ４ )-hydroxyalkyl, (C １ -C ４ )-Alkoxy - (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkoxy-(C １ -C ４ ) - Al Kill, (C ２ -C ４ )-alkenyl, (C ２ -C ４ )-alkenyloxy-(C １ -C ４ )-alkyl, (C ２ -C ４ )-haloalkenyloxy-(C １ -C ４ )-alkyl, ( C ２ -C ４ )-haloalkenyl, (C ２ -C ４ )-cyanoalkenyl, (C ２ -C ４ ) - Alkynyl, (C ２ -C ４ )-alkynyloxy-(C １ -C ４ )-alkyl, (C ２ - C ４ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloa Rukill - (C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-alkyl-(C ３ -C ６ ) -cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-Alkyl Thio-(C １ -C ４ )-alkyl, (C １ -C ４ )-Alkyl sulfinyl-(C １ -C ４ )-alkyl, (C １ -C ４ )-Alkylsulfonyl-(C １ -C ４ )-Alkyl or (C １ -C ４ )-alkylcarbonyl-(C １ -C ４ )-alkyl, R ５ , R ６ are independently hydrogen, cyano, halogen, (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkyl, (C ２ -C ４ )-alkenyl, (C ２ -C ４ ) - HaloArche Nil, (C ２ -C ４ )-alkynyl, (C ２ -C ４ )-haloalkynyl, (C ３ -C ６ ) -cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-Cycloalkyl , (C １ -C ４ )-alkyl-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ ) - Al Koxi, (C １ -C ４ )-haloalkoxy, (C １ -C ４ )-alkoxyimino, (C １ -C ４ )-alkylthio, (C １ -C ４ )-haloalkylthio, (C １ -C ４ ) -Archi Rusulfinyl, (C １ -C ４ )-haloalkylsulfinyl, (C １ -C ４ ) -Archi sulfonyl, (C １ -C ４ )-haloalkylsulfonyl, (C １ -C ４ ) -Alkyls sulfonyloxy, (C １ -C ４ )-alkylcarbonyl, (C １ -C ４ )-Haloalkyl Carbonyl, aminocarbonyl, (C １ -C ４ )-alkylaminocarbonyl, di-(C １ -C ４ )-alkylaminocarbonyl, (C １ -C ４ )-alkylsulfonylamino, (C １ -C ４ )-alkylamino, di-(C １ -C ４ )-Alkylamino, aminosulfo Nil, (C １ -C ４ )-alkylaminosulfonyl or di-(C １ -C ４ )-Alkyl is aminosulfonyl, n represents 0, 1 or 2; Here, if Q represents Q2, then R ｃ (C １ -C ４ )-does not represent haloalkyl; A compound of formula (I) according to claim 1.

4. R １ However, (C １ -C ４ )-alkyl, (C １ -C ４ )-haloalkyl or (C ３ -C ６ )-cycloalkyl, R ａ , R ｂ , R ｃ , R ｄ are each independently hydrogen, cyano, halogen, (C １ -C ４ )-alkyl, (C １ -C ４ )-alkoxy, (C １ -C ４ )-haloalkyl, (C １ - C ４ )-haloalkoxy, (C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-Alkyl Thio, (C １ -C ４ )-alkylsulfinyl, (C １ -C ４ )-alkylsulfonyl, (C １ -C ４ )-haloalkylthio, (C １ -C ４ )-haloalkylsulfinyl, (C １ -C ４ )-haloalkylsulfonyl, NHCO-(C １ -C ４ )-alkyl ((C １ -C ４ )-alkylcarbonylamino), NHCO—O(C １ -C ４ )-Alkyl (( C １ -C ４ )-alkoxycarbonylamino) or NHCO-(C ３ -C ６ )-Cyclo Alkyl ((C ３ -C ６ )-cycloalkylcarbonylamino), Here, the group R ａ , R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen; Q is a heteroaromatic 9- or 12-membered condensed ring selected from the group consisting of Q2, Q3 and Q16; represents a fused bicyclic or tricyclic ring system, R ４ However, (C １ -C ４ )-alkyl or (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkyl, R ５ is hydrogen, cyano, halogen, (C １ -C ４ )-alkyl, (C １ -C ４ ) -Halo Alkyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C ３ -C ６ )-cycloalkyl, (C １ -C ４ )-alkyl-(C ３ -C ６ )-Cycloalkoxy ru, (C １ -C ４ )-alkoxy, (C １ -C ４ )-haloalkoxy, (C １ -C ４ ) - Alkoxyimino, (C １ -C ４ )-alkylthio, (C １ -C ４ )-Haloalkylthio , (C １ -C ４ )-alkylsulfinyl, (C １ -C ４ )-Haloalkylsulfinyl , (C １ -C ４ )-alkylsulfonyl, (C １ -C ４ )-haloalkylsulfonyl, ( C １ -C ４ )-alkylcarbonyl, (C １ -C ４ )-haloalkylcarbonyl, (C １ -C ４ )-alkylaminocarbonyl, di-(C １ -C ４ )-Alkylaminocarbonyl , (C １ -C ４ )-alkylsulfonylamino, (C １ -C ４ )-Alkylaminosulfonate Nyl or di-(C １ -C ４ )-alkylaminosulfonyl, R ６ represents hydrogen, n represents 0, 1 or 2; Here, if Q represents Q2, then R ｃ (C １ -C ６ )-does not represent haloalkyl; A compound of formula (I) according to claim 1.

5. In the formula, R １ is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n- Butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl ethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, represents tetrafluoroethyl or pentafluoroethyl, R ａ , R ｂ , R ｃ , R ｄ are, independently of each other, hydrogen, fluorine, chlorine, bromine, iodine, Ano, methyl, ethyl, cyclopropyl, cyclobutyl, methoxy, ethylsulfonyl, Difluoromethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio O, trifluoroethylthio, trifluoroethylsulfinyl, trifluoroethylsulfinyl Sulfonyl, difluoroethoxy, trifluoroethoxy, 2,2-difluoropropoxy , methyl(carbonyl)amino, ethyl(carbonyl)amino, cyclopropyl(carbonyl)amino methoxy(carbonyl)amino or methoxy(carbonyl)amino; Here, the group R ａ , R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen, Q is a heteroaromatic 9- or 12-membered condensed ring selected from the group consisting of Q2, Q3 and Q16; represents a fused bicyclic ring system, R ４ represents methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl; 、 R ５ However, fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl Fluoroethyl (CH ２ C.F.H. ２ , C.H.F.C.H. ３ ), difluoroethyl (CF ２ CH ３ , C.H. ２ CHF ２ , CHFCFH ２ ), trifluoroethyl (CH ２ CF ３ , C HFCHF ２ , C.F. ２ C.F.H. ２ ), tetrafluoroethyl (CHFCF ３ , C.F. ２ CH F ２ ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, di Chlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or or trifluoromethylsulfonyl, R ６ represents hydrogen, n represents 0, 1 or 2; Here, if Q represents Q2, then R ｃ represents difluoromethyl or trifluoromethyl. No, A compound of formula (I) according to claim 1.

6. In the formula, R １ represents ethyl, R ａ represents hydrogen, R ｂ represents hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine, R ｃ are hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, difluoromethyl, thi trifluoromethyl, methoxy, methyl(carbonyl)amino (-NH-CO-Me), Cyclopropyl(carbonyl)amino (-NH-CO-cyclopropyl), methoxy ( Carbonyl)amino (-NH-CO-OMe), ethylsulfonyl, 2,2-difluoro 2,2,2-trifluoroethoxy, 2,2-difluoropropoxy (- OCH ２ CF ２ CH ３ ) or 2,2,2-trifluoroethylthio (2,2,2-trifluoroethylthio Trifluoroethylsulfanyl: -SCH ２ CF ３ ) R ｄ represents hydrogen, bromine, chlorine, cyano or trifluoromethyl; Here, the group R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen, Q is a heteroaromatic 9-membered fused bicyclic ring system selected from the group consisting of Q2, Q3 and Q16; represents R ４ represents methyl, R ５ is trifluoromethyl, pentafluoroethyl, trifluoromethoxy or thifluoromethyl. represents trifluoromethylsulfonyl, R ６ represents hydrogen, n represents 2; Here, if Q represents Q2, then R ｃ represents difluoromethyl or trifluoromethyl. No, A compound of formula (I) according to claim 1.

7. In the formula, R １ represents ethyl, R ａ represents hydrogen, R ｂ represents hydrogen or trifluoromethyl; R ｃ are hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, methoxy, methyl ( cyclopropyl(carbonyl)amino (-NH-CO-Me), cyclopropyl(carbonyl)amino ( -NH-CO-cyclopropyl), methoxy(carbonyl)amino (-NH-CO-O Me), ethylsulfonyl, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy Toxoxy, 2,2-difluoropropoxy (-OCH ２ CF ２ CH ３ ) or 2, 2, 2 -trifluoroethylthio, R ｄ represents hydrogen, bromine, chlorine, cyano or trifluoromethyl; Here, the group R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen, Q represents a heteroaromatic 9-membered fused bicyclic ring system from the group consisting of Q2; R ４ represents methyl, R ５ is trifluoromethyl, pentafluoroethyl, trifluoromethoxy or thifluoromethyl. represents trifluoromethylsulfonyl, R ６ represents hydrogen, n represents 2; A compound of formula (I) according to claim 1.

8. In the formula, R １ represents ethyl, R ａ represents hydrogen, R ｂ represents hydrogen, R ｃ represents hydrogen, R ｄ represents bromine, cyano or trifluoromethyl; Q represents a heteroaromatic 9-membered fused bicyclic ring system from the group consisting of Q3; R ４ represents methyl, R ５ represents trifluoromethyl or pentafluoroethyl; R ６ represents hydrogen, n represents 2; A compound of formula (I) according to claim 1.

9. In the formula, R １ represents ethyl, R ａ represents hydrogen, R ｂ represents hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine, R ｃ is hydrogen, chlorine, bromine, cyano, methyl, difluoromethyl or trifluoromethyl. It represents chill, R ｄ represents hydrogen, bromine or chlorine; Here, the group R ｂ , R ｃ Or R ｄ represents a substituent other than hydrogen, Q represents a heteroaromatic 9-membered fused bicyclic ring system from the group consisting of Q16; R ４ represents methyl, R ５ represents trifluoromethyl or pentafluoroethyl; R ６ represents hydrogen, n represents 2; A compound of formula (I) according to claim 1.

10. The structure: 【Chemistry 4】 【change】 【change】 【change】 【change】 【change】 2. The compound of formula (I) according to claim 1, having the formula:

11. Agricultural composition comprising a compound of formula (I) according to claim 1 and a filler and / or a surfactant. Drug preparations.

12. 12. The pesticide formulation of claim 11 further comprising an additional pesticide active compound.

13. A compound of formula (I) according to claim 1 or a pesticide formulation according to claim 11 or 12. A method for controlling pests, comprising applying the composition to pests and / or their habitats.

14. A compound of formula (I) according to claim 1 or claim 11 or claim 2 for controlling pests.

13. Use of the pesticide formulation according to claim 12.

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