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WO 2013/150015 Al 10 October 2013 (10.10.2013) P O P C T

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WO 2013/150015 Al 10 October 2013 (10.10.2013) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2013/150015 Al 10 October 2013 (10.10.2013) P O P C T (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, C07D 209/54 (2006.01) A01N 43/38 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, C07D 471/10 (2006.01) A01N 43/90 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (21) International Application Number: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, PCT/EP2013/056915 ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (22) International Filing Date: NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, 2 April 2013 (02.04.2013) RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (25) Filing Language: English ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 12162982.8 3 April 2012 (03.04.2012) EP GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, (71) Applicant: SYNGENTA PARTICIPATIONS AG TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, [CH/CH]; Schwarzwaldallee 215, CH-4058 Basel (CH). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (72) Inventors: MUEHLEBACH, Michel; Syngenta Crop Pro TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, tection Munchwilen AG, Schaffhauserstrasse, CH-4332 ML, MR, NE, SN, TD, TG). Stein (CH). BUCHHOLZ, Anke; Syngenta Crop Protec tion Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein Declarations under Rule 4.17 : (CH). RENOLD, Peter; Syngenta Crop Protection — as to applicant's entitlement to apply for and be granted a Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein patent (Rule 4.1 7(H)) (CH). — of inventorship (Rule 4.17(iv)) (74) Agent: JANTSCHY, Jasmin; Syngenta International AG, Intellectual Property, WRO- 1004-6-22, Schwarzwaldallee Published: 215, CH-4058 Basel (CH). — with international search report (Art. 21(3)) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (54) Title: 1 - AZA - SPIRO [4.5] DEC- 3 - ENE AND 1, 8 - DIAZA - SPIRO [4.5 ] DEC- 3 - ENE DERIVATIVES AS PESTI CIDES (57) Abstract: A compound of the formula (I), wherein the substituents are as defined in claim 1, are useful as a pesticides. 1 - AZA - SPIRO [4.5] DEC- 3 - ENE AND 1 , 8 - DIAZA - SPIRO [4.5 ] DEC- 3 - ENE DERIVATIVES AS PESTICIDES The present invention relates to new N-phenyl amide substituted spiroheterocyclic pyrrolidine dione derivatives, to processes for preparing them , to pesticidal, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests. Spiroheterocyclic pyrrolidine dione derivatives are disclosed for example in US 6555567, US 6479489, US 67741 33, EP 596298, WO 98/05638 and WO 99/48869. Further, spiroheterocyclic pyrrolidine dione derivatives are known, for example, from WO 09/049851 , WO 2010/063670, WO 201 0/066780 and WO 11/ 15 1 199. It has now surprisingly been found that novel N-phenyl amide substituted spiroheterocyclic pyrrolidine dione derivatives have good insecticidal properties. This is surprising because such a phenyl ring contributes to an overall molecular increase in bulk and lipophilicity, properties which up until now were considered to prevent this class of compounds from having biological activity against pests. The opposite has now been observed . Such N-phenyl amide substituted spiroheterocyclic pyrrolidine dione derivatives have not been individualised in the prior art. The present invention therefore provides compounds of the formula I wherein X , Y and Z independently of each other are C -4alkyl , C3-6cycloalkyl, C -4haloalkyl, C -4alkoxy, C2-6alkenyl, C2-6alkynyl, halogen, cyano, phenyl or phenyl substituted by C -4alkyl, C -4haloalkyl, halogen or cyano; m and n, independently of each other, are 0, 1, 2 or 3 and m+n is 0 , 1, 2 or 3; G is hydrogen , a metal , ammonium, sulfonium or a latentiating group; R' is C -4alkyl, C -4haloalkyl , C -4alkoxy, C -4haloalkoxy, C -4alkylthio, halogen or cyano; k is 0, 1, 2 , 3, 4 or 5; when k is 2 , 3, 4 or 5, then two adjacent R' taken together may form a fragment or -OCF 20-; and W is a group selected from W to W 2 : wherein R is hydrogen, C -6alkyl, C -6haloalkyl, C -6cyanoalkyl, C2-6alkenyl, C2-6haloalkenyl, C3-6alkynyl , benzyl, Ci- 4alkoxy(Ci-4)alkyl or Ci- 4alkoxy(Ci-4)alkoxy(Ci-4)alkyl; or an agrochemically acceptable salt or an N-oxide thereof. In the compounds of the formula I, each alkyl moiety either alone or as part of a larger group is a C-i-4 - or C -6 -straight or branched chain and is, for example, methyl, ethyl, n-propyl, n- butyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl and n-hexyl. Alkoxy groups have a preferred chain length of from 1 to 4 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy or tert- butoxy. Such groups can be part of a larger group such as alkoxyalkyl and alkoxyalkoxyalkyl. Alkoxyalkyl groups preferably have a chain length of 1 to 4 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, isopropoxymethyl. Alkoxyalkoxyalkyl groups preferably have a chain length of 1 to 4 carbon atoms. Alkoxyalkoxyalkyl is, for example, methoxymethoxymethyl, methoxyethoxymethyl, ethoxymethoxyethyl and ethoxyethoxyethyl. This also applies, correspondingly, to alkylthio which is, for example, thiomethyl. - - Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or haloalkenyl. Haloalkyl groups preferably have a chain length of from 1 to 4 or 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl , trichloromethyl, 2,2,2-trifluoroethyl , 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2- trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl. The preferred alkenyl and alkynyl radicals having 2 to 6 or 3 to 6 carbon atoms can be straight or branched and can contain more than one double or triple bond respectively. Examples are vinyl, (E)- or (Z)-propenyl, 2-methyl-propenyl, allyl, 3-methyl-but-2-enyl, ethynyl, prop-1 -ynyl, propargyl, butenyl, butynyl , pentenyl and pentynyl. The cycloalkyl groups preferably have from 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Phenyl, also as part of a substituent such as benzyl, may be substituted , preferably by one C C C or more -4alkyl, -4haloalkyl, -4alkoxy, halogen or cyano groups. The substituents can be in ortho, meta and/or para position. In the compounds of the formula I, k is preferably 0 , 1 or 2 . Even more preferred are compounds of the formula I wherein k is 0 or 1. If k =1, 2 , 3 , 4 or 5 , each substituent R' of the phenyl ring can be independently the same or different. In the compounds of formula I, R' is C C C C C the substituent -4alkyl, -4haloalkyl , -4alkoxy, -4haloalkoxy, -4alkylthio, halogen or cyano. Preferably, R' is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec- butyl, iso-butyl, tert-butyl, fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl , 2-fluoroethyl, 2- chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, trifluoromethoxy, thiomethyl, thioethyl, thio-iso-propyl, fluorine, chlorine, bromine, iodine or cyano. More preferably, R' is selected from methyl , ethyl, n-propyl, iso- propyl, fluoromethyl, difluoromethyl, difluorochloromethyl , trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl , methoxy, ethoxy, propoxy, i-propoxy, trifluoromethoxy, - thiomethyl, fluorine, chlorine, or cyano. The substituents R' can be in ortho, meta and/or para position. Preferably, W is a group selected from one of W2 to wherein R is defined as above, preferably a hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, trifluoromethyl, allyl, propargyl, benzyl, methoxymethyl, ethoxymethyl or methoxyethyl. More referabl W is a rou selected from one of W2 to wherein R is defined as above, preferably a hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, trifluoromethyl, allyl, propargyl, benzyl, methoxymethyl, ethoxymethyl or methoxyethyl. Even more preferably, W is a group selected from one of W2 or W to W 2 : wherein R is defined as above, preferably a hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, trifluoromethyl, allyl, propargyl, benzyl, methoxymethyl, ethoxymethyl or methoxyethyl. Most preferably, W is a group selected from one of W2: \ W2 = ^N-O-R wherein R is defined as above, preferably a hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, trifluoromethyl, allyl, propargyl, benzyl, methoxymethyl, ethoxymethyl or methoxyethyl. The latentiating groups G (i.e. groups which are metabolizable in a plant; in an insect, acarine, mollusc and/or nematode pest; and/or in the soil) are selected to allow its removal by one or a combination of biochemical, chemical or physical processes to afford compounds of formula I where G is hydrogen before, during or following application to the treated area or plants.
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