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Pesticidally Active Heterocyclic Derivatives with Sulphur Containing Substituents

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Pesticidally Active Heterocyclic Derivatives with Sulphur Containing Substituents (19) TZZ¥___T (11) EP 3 166 941 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 471/04 (2006.01) C07F 5/02 (2006.01) 10.01.2018 Bulletin 2018/02 A01N 43/90 (2006.01) A01P 7/04 (2006.01) (21) Application number: 15733741.1 (86) International application number: PCT/EP2015/065095 (22) Date of filing: 02.07.2015 (87) International publication number: WO 2016/005263 (14.01.2016 Gazette 2016/02) (54) PESTICIDALLY ACTIVE HETEROCYCLIC DERIVATIVES WITH SULPHUR CONTAINING SUBSTITUENTS PESTIZIDWIRKSAME HETEROZYKLISCHE DERIVATE MIT SCHWEFELHALTIGEN SUBSTITUENTEN DÉRIVÉS HÉTÉROCYCLIQUES ACTIFS SUR LE PLAN PESTICIDE AVEC DES SUBSTITUANTS CONTENANT DU SOUFRE (84) Designated Contracting States: • EDMUNDS, Andrew AL AT BE BG CH CY CZ DE DK EE ES FI FR GB CH-4332 Stein (CH) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • JUNG, Pierre Joseph Marcel PL PT RO RS SE SI SK SM TR CH-4332 Stein (CH) • EMERY, Daniel (30) Priority: 08.07.2014 EP 14176055 CH-4332 Stein (CH) 11.03.2015 EP 15158668 • MUEHLEBACH, Michel CH-4332 Stein (CH) (43) Date of publication of application: • RENOLD, Peter 17.05.2017 Bulletin 2017/20 CH-4332 Stein (CH) (73) Proprietor: Syngenta Participations AG (74) Representative: Syngenta International AG 4058 Basel (CH) WRO B8-Z1-30 Schwarzwaldallee 215 (72) Inventors: 4058 Basel (CH) • STOLLER, André CH-4332 Stein (CH) (56) References cited: • JEANGUENAT, André WO-A1-2012/086848 WO-A1-2013/018928 CH-4332 Stein (CH) 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 3 166 941 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 166 941 B1 Description [0001] The present invention relates to pesticidally active, in particular insecticidally active heterocyclic derivatives containing sulphur substituents, to intermediates for the preparation of those compounds, to compositions comprising 5 those compounds, and to their use for controlling animal pests (including arthropods and in particular insects or repre- sentatives of the order Acarina). [0002] Heterocyclic compounds with pesticidal action are known and described, for example, in WO 2012/086848 and WO 2013/018928. [0003] There have now been found novel pesticidally active heterocyclic 6/5-bicyclic ring derivatives with sulphur 10 containing phenyl and pyridyl substituents. [0004] The present invention accordingly relates to compounds of formula I, 15 20 wherein A represents CH or N; 25 each R is, independently from each other,1-C4 alkyl,C C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylsulfanyl, 1C-C4haloalkylsulfanyl, 1C-C4alkylsulfinyl, 1C-C4haloalkylsulfinyl, 1C-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, 1-C6alkylcarbonyl,C 1-C6haloalkylcarbonyl,C 1-C6alkoxycarbonyl,C C1-C6haloalkoxycarbonyl, C1-C6alkylamino, C2-C8dialkylamino, halogen, cyano, cyanoC 1-C4alkyl, tri(C 1-C4alkyl)si- lyl, C1-C4alkoxyC1-C4alkoxy, C1-C4alkylsulfanylC1-C4alkoxy or nitro; or each R is, independently from each other, 30 phenyl, pyrimidinyl, thiazolyl, pyridinyl, imidazolyl, pyrazolyl, oxazolyl or oxadiazolyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, imidazolyl, pyrazolyl, oxazolyl or oxadiazolyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1-C6alkyl and cyano; n is 0, 1, 2, 3, 4 or 5; X is S, SO or SO2 35 R1 is C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C4alkyl, C3-C6cycloalkyl mono-, di- or trisub- stituted by substituents selected from the group consisting of halogen, cyano and C 1-C4alkyl;or R 1 is C 3-C6cycloalkyl- C1-C4alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl; or R1 is C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl; 40 R2 is halogen, C1-C4haloalkyl or C1-C4haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or 2R is 1-CC4haloalkylsulfanyl, 1C-C4haloalkylsulfinyl, 1C-C4haloalkylsulfonyl, O(C1-C4haloalkyl) or -C(O)C1-C4haloalkyl; or R2 is C3-C6cycloalkyl which can be mono - or polysubstituted by substituents selected from the group consisting 45 of halogen, cyano and C1-C4alkyl; and X1 is O, S or NR3, wherein R3 is hydrogen, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy-C1-C4alkyl or C3-C6cycloalkyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds. 50 [0005] Compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrose acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as C 1-C4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such 55 as hydroxycarboxylic acids, for example ascorbic acid, lacticacid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as 1C-C4alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal 2 EP 3 166 941 B1 or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine. [0006] The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for 5 example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, nonyl, decyl and their branched isomers. Alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated. [0007] Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl. 10 [0008] Haloalkyl groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluor- omethyl, 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. [0009] Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomeric pentyloxy and hexyloxy radicals. 15 [0010] Alkoxyalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. [0011] Alkoxycarbonyl is for example methoxycarbonyl (which is C 1alkoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl or hexoxycarbonyl. 20 [0012] The cycloalkyl groups preferably have from 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. [0013] In the context of this invention "mono- to polysubstituted" in the definition of the substituents, means typically, depending on the chemical structure of the substituents, monosubstituted to seven-times substituted, preferably mon- osubstituted to five-times substituted, more preferably mono-, double- or triple-substituted. 25 [0014] The compounds of formula I according to the invention also include hydrates which may be formed during the salt formation. [0015] In an embodiment of the invention, compounds of formula I are preferred, wherein each R is, independently from each other, C 1-C4alkyl, C 1-C4haloalkyl, C 1-C4alkoxy, C 1-C4haloalkoxy, C 1-C4alkylsulfanyl, C1-C4haloalkylsulfanyl, 1C-C4alkylsulfinyl, 1C-C4haloalkylsulfinyl, 1C-C4alkylsulfonyl, 1C-C4haloalkylsulfonyl, 30 C1-C6alkylcarbonyl, 1C-C6haloalkylcarbonyl, 1C-C6alkoxycarbonyl, 1C-C6haloalkoxycarbonyl, 1C-C6alkylamino, C2-C8dialkylamino, halogen, cyano or nitro; R1 is C 1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C4alkyl, C3-C6cycloalkyl mono-di- or trisubstituted by halogen; or R1 is C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl; R2 is halogen, C1-C4haloalkyl or C1-C4haloalkyl substituted by one or two hydroxyl; or R2 is C1-C4haloalkylsulfanyl, 35 C1-C4haloalkylsulfonyl or O(C1-C4haloalkyl). [0016] A preferred group of compounds of formula I is represented by the compounds of formula I-1 40 45 wherein R, R2 and n are as defined under formula I above; Xa1 is S, SO or SO2 50 Ra1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; and agrochemically acceptable
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