(19) TZZ__ _T (11) EP 1 812 421 B9 (12) CORRECTED EUROPEAN PATENT SPECIFICATION (15) Correction information: (51) Int Cl.: Corrected version no 1 (W1 B1) C07D 401/04 (2006.01) A01N 43/56 (2006.01) Corrections, see C07D 401/00 (2006.01) C07D 233/72 (2006.01) Claims EN 7 (86) International application number: (48) Corrigendum issued on: PCT/US2005/042196 25.09.2013 Bulletin 2013/39 (87) International publication number: (45) Date of publication and mention WO 2006/055922 (26.05.2006 Gazette 2006/21) of the grant of the patent: 24.04.2013 Bulletin 2013/17 (21) Application number: 05851952.1 (22) Date of filing: 18.11.2005 (54) ANTHRANILAMIDE INSECTICIDES ANTHRANILAMID-INSEKTIZIDE INSECTICIDES A BASE D’ANTHRANILAMIDES (84) Designated Contracting States: • TAGGI, Andrew, Edmund AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Newark, DE 19711 (US) HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI • BEREZNAK, James, Francis SK TR Newtown Square, PA 19073 (US) (30) Priority: 18.11.2004 US 629120 P (74) Representative: Beacham, Annabel Rose 10.06.2005 US 689414 P Dehns St Bride’s House (43) Date of publication of application: 10 Salisbury Square 01.08.2007 Bulletin 2007/31 London EC4Y 8JD (GB) (60) Divisional application: 12194234.6 / 2 564 706 (56) References cited: WO-A-01/70671 WO-A-02/48137 (73) Proprietor: E.I. DU PONT DE NEMOURS AND WO-A-03/015518 WO-A-03/015518 COMPANY WO-A-03/024222 WO-A-03/024222 Wilmington, DE 19898 (US) WO-A-03/026415 WO-A-2004/046129 WO-A-2004/067528 WO-A-2005/077934 (72) Inventors: WO-A-2006/040113 JP-A- 2003 034 671 • LAHM, George, Philip Wilmington, DE 19808 (US) Remarks: • SELBY, Thomas, Paul Thefile contains technical information submitted after Hockessin, DE 19707 (US) the application was filed and not included in this • STEVENSON, Thomas, Martin specification Newark, DE 19702 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 812 421 B9 Printed by Jouve, 75001 PARIS (FR) EP 1 812 421 B9 Description [0001] This invention relates to certain anthranilamides, their N-oxides, salts and compositions suitable for agronomic and nonagronomic uses, and non- therapeutic methods of their use for controlling invertebrate pests such as arthropods 5 in both agronomic and nonagronomic environments. BACKGROUND OF THE INVENTION [0002] The control ofinvertebrate pests isextremely importantin achieving high cropefficiency. Damage by invertebrate 10 pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, turf, wood products, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action. 15 [0003] PCT Patent Publication WO 03/015518 discloses N-acyl anthranilic acid derivatives of Formula i as arthropodi- cides 20 25 30 35 1 wherein, inter alia, A and B are independently O or S; R is H, C 1-C6 alkyl, C 2-C6 alkoxycarbonyl or C 2-C6 alkylcarbonyl; 2 3 R is H or C1-C6 alkyl; and R is H or optionally substituted C 1-C6 alkyl, C 2-C6 alkenyl, C 2-C6 alkynyl, or C 3-C6 cycloalkyl. [0004] PCT PATENT APPLICATION WO 03/024222 discloses anthranilamide derivatives and their use against in- secticidal pests. 40 SUMMARY OF THE INVENTION [0005] This invention is directed to compounds of Formula 1 including all geometric and stereoisomers, N-oxides, and agronomic or nonagronomic salts thereof, agricultural and nonagricultural compositions containing them and their use for controlling invertebrate pests: 45 50 55 2 EP 1 812 421 B9 wherein: J is 5 10 15 1a R is CH3, F, Cl, Br or I; 1b R is H, CH3, CF3, CN, F, Cl, Br or I; R2 and R3 are H; 4 R is 2-oxetanylmethyl, 3-oxetanylmethyl or 3-oxetanyl, each optionally substituted with 1 to 2 CH 3; 6 R is Cl, Br, OCH2CF3 or CF3; and 20 R7 is 25 30 and 9 each R is independently H, CH3, CF3, CN or halogen. 35 [0006] This invention also provides a composition comprising a compound of Formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, said composition optionally further comprising at least one additional biologically active compound or agent. [0007] This invention also provides a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of a 40 surfactant, a solid diluent and a liquid diluent, said composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent. [0008] This invention further provides a spray composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula 1 or the composition described above and a propellant. This invention also provides a bait composition for controlling an invertebrate pest comprising a biologically effective amount of a compound 45 of Formula 1 or the composition described above, one or more food materials, optionally an attractant, and optionally a humectant. [0009] This invention further provides a trap device for controlling an invertebrate pest comprising said bait composition and a housing adapted to receive said bait composition, wherein the housing has at least one opening sized to permit the invertebrate pest to pass through the opening so the invertebrate pest can gain access to said bait composition from 50 a location outside the housing, and wherein the housing is further adapted to be placed in or near a locus of potential or known activity for the invertebrate pest. [0010] This invention also provides a non- therapeutic method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). This invention also relates to such non- therapeutic method wherein the invertebrate pest 55 or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, said composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent. 3 EP 1 812 421 B9 DETAILS OF THE INVENTION [0011] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains" or "containing," or any other variation thereof, are intended to cover a non- exclusive inclusion. For example, a composition, 5 a mixture, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, method, article, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). 10 [0012] Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. [0013] The term "halogen" includes fluorine, chlorine, bromine or iodine. 15 [0014] Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stere- oisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from For- 20 mula 1, N-oxides, and agronomic and nonagronomic suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form. [0015] One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form 25 N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.