(19) TZZ Z¥ _T (11) EP 2 606 732 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 26.06.2013 Bulletin 2013/26 A01N 43/713 (2006.01) A01N 63/00 (2006.01) A01N 63/02 (2006.01) A01N 63/04 (2006.01) (2009.01) (2009.01) (21) Application number: 11194336.1 A01N 65/00 A01N 65/22 A01N 31/08 (2006.01) A01P 7/04 (2006.01) (22) Date of filing: 19.12.2011 (84) Designated Contracting States: (71) Applicant: Bayer CropScience AG AL AT BE BG CH CY CZ DE DK EE ES FI FR GB 40789 Monheim (DE) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (72) Inventor: The designation of the inventor has not Designated Extension States: yet been filed BA ME (54) Use of an anthranilic diamide derivatives with heteroaromatic and heterocyclic substituents in combination with a biological control agent (57) A composition comprising a compound of for- in which R1, R2, R3, R4, R5, R6, A, Q and n can have the mula (I): definitions stated in the description, and at least one bi- ological control agent selected from bacteria, fungi or yeasts, protozoas, viruses, entomopathogenic nema- todes, and botanical extracts, or products produced by microorganisms including proteins or secondary metabolites" and optionally an inoculant, for reducing overall damage of plants and plant parts as well as losses in harvested fruits or vegetables caused by insects, nem- atodes and phytopathogens. EP 2 606 732 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 606 732 A1 Description [0001] The present invention relates to the use of anthranilic diamide derivatives with heteroaromatic and heterocyclic substituents in combination with a biological control agent as well as to a preparation method of compositions containing 5 anthranilic diamide derivatives and a selected biological control agent, and compositions containing anthranilic diamide derivatives and at least one biological control agent. [0002] It is already known that certain anthranilamides (e.g. WO 01/70671, WO 03/015519, WO 03/016284, WO 03/015518, WO 03/024222, WO 03/016282, WO 03/016283, WO 03/062226, WO 03/027099, WO 04/027042, WO 04/033468, WO 2004/046129, WO 2004/067528, WO 2005/118552, WO 2005/077934, WO 2005/085234, WO 10 2006/023783, WO 2006/000336, WO 2006/040113, WO 2006/111341, WO 2007/006670, WO 2007/024833, WO 2007/020877) are useful for combating harmful pests which occur in agriculture. Several methods to apply such com- pounds are described therein. [0003] However, environmental and economic requirements imposed in modern-day crop protection agents are con- tinually increasing. This is particularly true with regard to the spectrum of action, toxicity, selectivity, application rate, 15 and formation of residues. Additionally, when applying agrochemicals, there are always the problems with resistances. Thus, there is a constant need for developing new, alternative plant protection agents which in some areas at least help to fulfil the abovementioned requirements. Moreover, there is a constant need to develop novel plant treatment agents which are particularly environmentally friendly. Also, as concerns regarding a possible impact of agrochemicals on the environment and the health of humans and animals are growing in the public opinion, efforts have to be made to reduce 20 the amount of agrochemicals applied. [0004] The inventors now surprisingly found that specific anthranilic diamide derivatives can be combined with selected biological control agents and thus satisfying above mentioned needs. The inventors even found that a synergistic activity increase occurs by combining selected anthranilic diamide derivatives with selected biological control agents. [0005] Thus, the invention is directed to the use of anthranilic acid diamide derivatives with heteroaromatic and het- 25 erocyclic substituents of formula (I) 30 35 1 R represents hydrogen, amino or hydroxyl or represents1 -CC6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or 40 C3-C6-cycloalkyl each of which is unsubstituted or substituted one or more times by identical or different substituents selectable independently of one another from halogen, cyano, nitro, hydroxyl, C 1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, (C1-C4-alkoxy)carbonyl, C1-C4-alkylamino, di (C1-C4-alkyl)amino, C3-C6-cycloalkylamino or (C1-C4-alkyl)C3-C6-cycloalkyl-amino, 45 2 R represents hydrogen, 1C-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, C2-C6alkoxycarbonyl or C2-C6-alkylcar- bonyl, 3 R represents hydrogen or represents C 1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl each of which 50 is optionally substituted one or more times by identical or different substituents selectable independently of one another from halogen, cyano, nitro, hydroxyl,1-C 6C-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylsulphimino, C1-C4-alkylsulphimino-C1-C4-alkyl, C1-C4-alkylsulphimino-C2-C5-alkylcarbonyl, C1-C4-alkylsulphoximino, C1-C4-alkylsulphoximino-C1-C4-alkyl, C1-C4-alkylsulphoximino-C2-C5-alkylcarbonyl, C2-C6-alkoxycarbo- 55 nyl, C2-C6-alkylcarbonyl or C3-C6-trialkylsilyl, 3 R further represents C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl each of which is optionally substituted one or more times by identical or different substituents selectable independently of one another 2 EP 2 606 732 A1 from amino, C3-C6-cycloalkylamino or a 5- or 6-membered heteroaromatic ring, 3 R likewise further represents C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C6-alkyl and C4-C12-bicycloalkyl, the substituents being selectable independently of one another from halogen, cyano, nitro, hydroxyl, amino, 5 C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylamino, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylsulphimino, C1-C4-alkylsulphimino-C1-C4-alkyl, C1-C4-alkylsulphimino-C2-C5-alkylcarbonyl, C1-C4-alkylsulphoximino, C1-C4-alkylsulphoximino-C1-C4- alkyl, C1-C4-alkylsulphoximino-C2-C5-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6- trialkylsilyl or a 5- or 6-membered heteroaromatic ring, 10 R2 and R3 can be joined to one another via two to six carbon atoms and form a ring which where appropriate additionally contains a further nitrogen, sulphur or oxygen atom and where appropriate may be substituted one to four times by C1-C2-alkyl, halogen, cyano, amino or C1-C2-alkoxy, 15 2 3 R and R further together represent =S(C1-C4-alkyl)2 or =S(O)(C1-C4-alkyl)2, 4 R represents hydrogen, halogen, cyano, nitro, C 1-C4-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C6-haloalke- nyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, SF5, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4- alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylami- 20 no, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C4-alkoxy)imino, (C1-C4-alkyl)(C1-C4-alkoxy)imino, (C1-C4-haloalkyl)(C1-C4-alkoxy)imino or C3-C6-trialkylsilyl, or 4 two R s, via adjacent carbon atoms, form a ring which represents -(CH 2)3-, -(CH2)4-, -(CH2)5-, - (CH=CH-)2-, -OCH2O-, -O(CH2)2O-, -OCF2O-, -(CF2)2O-, -O(CF2)2O-, -(CH=CH-CH=N)- or - (CH=CH-N=CH)-, 25 two R4s further, via adjacent carbon atoms, form the following fused rings, which where appropriate are substituted one or more times by identical or different substituents selectable independently of one another from hydrogen, C 1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, C1-C6-alkoxy, C1-C4-alkylthio(C1-C6-alkyl), C1-C4- alkylsulphinyl(C1-C6-akyl), C1-C4-alkylsulphonyl(C1-C6-alkyl), C1-C4-alkylamino, di(C1-C4-alkyl)amino or C3-C6-cy- cloalkylamino, 30 35 40 45 50 n represents 0 to 3, 5 R represents C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalke- 55 nyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, halogen, cyano, nitro or C3-C6-trialkylsilyl, 3 EP 2 606 732 A1 6 R represents hydrogen, 1-CC6-alkyl, 2C-C6-alkenyl, 2C-C6-alkynyl, 3C-C6-cycloalkyl, 1C-C6-haloalkyl, C2-C6-haloalkenyl or 5 10 6 R further represents C3-C6-cycloalkoxy, 7 R represents independently at each occurrence hydrogen, C 1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, 15 m represents 0 to 4, X represents N, CH, CF, CCl, CBr or CI, A represents -CH2-, -CH2O- -CH2OCH2-, -CH2S-, -CH2SCH2-, -CH2N(C1-C6-alkyl)-, -CH2N(C1-C6-alkyl)CH2-, -CH 20 [CO2(C1-C6-alkyl)]-, -CH(CN)-, -CH(C1-C6-alkyl)-, -C(di-C1-C6-alkyl)-, - CH2CH2- or -C=NO(C1-C6-alkyl)-, Q represents a 5- or 6-membered heteroatomatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, the ring system being unsubstituted or substituted one or more times by identical or different substit- uentsselectable independently ofone another from hydrogen, C 1-C6-alkyl,C 2-C6-alkenyl,C 2-C6-alkynyl, C 3-C6-cy- 25 cloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, 1(C-C6-alkyl)carbonyl, 1(C-C6-alkoxy)carbonyl,