(12) Patent Application Publication (10) Pub. No.: US 2014/0148471 A1 BRETSCHINEDER Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0148471 A1 BRETSCHINEDER Et Al US 20140148471 A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0148471 A1 BRETSCHINEDER et al. (43) Pub. Date: May 29, 2014 (54) HETEROCYCLIC COMPOUNDSAS (60) Provisional application No. 61/359,058, filed on Jun. PESTICIDES 28, 2010. (71) Applicant: Bayer CropScience AG, Monheim (DE) (30) Foreign Application Priority Data (72) Inventors: Thomas BRETSCHNEIDER, Lohmar Jun. 28, 2010 (EP) .................................. 10167453.9 (DE); Reiner FISCHER, Monheim Mar. 24, 2011 (EP) .................................. 11159576.5 (DE); Martin FULEIN, Dusseldorf (DE); Peter JESCHKE, Bergisch Gladbach (DE); Adeline KOHLER, Publication Classification Wuppertal (DE); Joachim KLUTH, (51) Int. Cl. Langenfeld (DE); Friedrich August AOIN 43/56 (2006.01) MUHLTHAU, Bad Sodenam Taunus AOIN 413/40 (2006.01) (DE); Yoshitaka SATO, Ibaraki (JP): (52) U.S. Cl. Arnd VOERSTE, Koln (DE); Eiichi CPC ................ A0IN 43/56 (2013.01); A0IN 43/40 SHIMOJO, Oyama-shi (JP) (2013.01) (73) Assignee: Bayer CropScience AG, Monheim (DE) USPC ........... 514/256; 544/322:546/256; 514/333; 546/270.4: 514/341 (21) Appl. No.: 14/169,849 (57) ABSTRACT (22) Filed: Jan. 31, 2014 The present application relates to novel heterocyclic com Related U.S. Application Data pounds, to the use thereof for controlling animal pests, which (62) Division of application No. 13/171,030, filed on Jun. include arthropods and especially insects, and to processes 28, 2011, now Pat. No. 8,686,004. for preparing the novel compounds. US 2014/0148471 A1 May 29, 2014 HETEROCYCLIC COMPOUNDSAS in which the arrow in each case marks the bond to the adjacent PESTICIDES r19,Fois) R" in the case of the heterocycles (A) and (D) is 0001. The present application relates to novel heterocyclic hydrogen, halogen, cyano, alkyl, alkoxy, amino, alky compounds, to processes for preparation thereof and to the lamino, dialkylamino, alkylthio or haloalkyl and use thereof for controlling animal pests, which include arthro I0010) R' in the case of heterocycle (C) is hydrogen, alkyl pods and especially insects, and also to intermediates for or haloalkyl, preparation of the heterocyclic compounds. 0011 B is hydrogen, halogen, cyano, nitro, alkyl, 0002 Particular thiazolyl, thiadiazolyl and pyrazolyl cycloalkyl, haloalkyl, amino, alkylamino, dialkylamino, compounds have already become known as insecticidally alkylthio or alkoxy and active ingredients (cf. WO 2010/006713 A2). (0012) G is optionally substituted heterocyclyl, optionally 0003 Modern crop protection compositions have to meet substituted heteroaryl or optionally substituted aryland many demands, for example in relation to the level, duration I0013 G' is a radical from the group of and breadth of their action and possible use. Questions of toxicity and of combinability with other active ingredients or (E) formulation auxiliaries play a role, as does the question of the X (O) expense that the synthesis of an active ingredient requires. In addition, resistances can occur. For all these reasons, the N1Ns. search for novel crop protection compositions cannot be con sidered to be complete, and there is a constant need for novel compounds having properties which, compared to the known (F) compounds, are improved at least in relation to individual aspects. 0004. It was an object of the present invention to provide compounds which widen the spectrum of the pesticides in various respects. 0005. This object, and further objects which are not stated (G) explicitly but can be discerned or derived from the connec tions discussed herein, are achieved by novel compounds of the formula (I) (I) 4 1N GS - (H) Al-- y N4 in which I0006 A' and A are each independently hydrogen, halo (I) gen, cyano, nitro, alkyl, cycloalkyl or alkoxy, 0007 G' is N or C-A' and 0008 G is a radical from the group of (A) (J) (B) (K) (O) (C) 1NNS 1 N f and L (O), X (L) (D) (M) US 2014/0148471 A1 May 29, 2014 0014) and in the case of the heterocycles (A), (B) and (0024) R' is hydrogen or alkyl, (C) is also the radical I0025I RandR may also form, together with the nitrogen atoms to which they are bonded, a Saturated or unsaturated and optionally substituted 4- to 8-membered ring which (N) may contain at least one further heteroatom from the group of Sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen and/or at least one carbonyl group, I0026 Rand R7 in the radical (E) may also form, together with the N—S(O), group to which they are bonded, a 0015 in which the arrow in each case marks the bond to saturated or unsaturated and optionally Substituted 4- to G, 8-membered ring which may contain one or more further 0016 X is oxygen or Sulphur, heteroatoms from the group of Sulphur, oxygen (where 0017 n is 1 or 2, oxygen atoms must not be immediately adjacent) and 0018 R is a radical from the group of hydrogen, alkyl, nitrogen and/or at least one carbonyl group, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl (0027 R and R7 may also form, together with the N–S and alkoxyalkyl, in each case optionally halogen-Substi (O) group to which they are bonded, a Saturated or unsat tuted alkylcarbonyl and alkylsulphonyl, in each case urated and optionally substituted 4- to 8-membered ring optionally halogen-substituted alkoxycarbonyl, in each which may contain one or more further heteroatoms from case optionally halogen-, alkyl-, alkoxy-, haloalkyl- and the group of Sulphur, oxygen (where oxygen atoms must cyano-Substituted cycloalkylcarbonyl, or a cation, for not be immediately adjacent) and nitrogen and/or at least example a mono- or divalent metal ion or an optionally one carbonyl group, alkyl- or arylalkyl-substituted ammonium ion, 10028. RandR may also form, together with the nitrogen 0019 Rand Rare each independently a radical from the atom to which they are bonded, a saturated or unsaturated group of in each case optionally Substituted alkyl, alkenyl and optionally substituted 4- to 8-membered ring which and alkynyl, in each case optionally substituted cycloalkyl, may contain one or more further heteroatoms from the cycloalkylalkyl and cycloalkenyl, in which the rings may group of Sulphur, oxygen (where oxygenatoms must not be contain at least one heteroatom from the group of Sulphur, immediately adjacent) and nitrogen and/or at least one oxygen (where oxygen atoms must not be immediately carbonyl group, adjacent) and nitrogen, in each case optionally substituted 0029 L is oxygen or sulphur, aryl, heteroaryl, arylalkyl and heteroarylalkyl and an I0030 R and R'' are each independently an in each case optionally Substituted amino group, optionally Substituted radical from the group of alkyl, alk 0020 R and R may also form, together with the N–S enyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, (O) group to which they are bonded, a saturated or unsat cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alky urated and optionally substituted 4- to 8-membered ring lthio, alkenylthio, phenoxy, phenylthio, benzyloxy, ben which may contain one or more further heteroatoms from Zylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy the group of Sulphur, oxygen (where oxygen atoms must and heteroarylalkylthio. not be immediately adjacent) and nitrogen and/or at least I0031) R' and R' may also form, together with the phos one carbonyl group, phorus atom to which they are bonded, a saturated or unsat I0021) R' is a radical from the group of in each case option urated and optionally substituted 5- to 7-membered ring ally substituted alkyl, alkoxy, alkenyl and alkynyl, in each which may contain one or two heteroatoms from the group case optionally Substituted cycloalkyl, cycloalkylalkyl and of oxygen (where oxygen atoms must not be immediately cycloalkenyl, in which the rings may contain at least one adjacent) and Sulphur, and heteroatom from the group of Sulphur, oxygen (where oxy 10032) R'' and R'' are each independently an in each case genatoms must not be immediately adjacent) and nitrogen, optionally Substituted radical from the group of alkyl, alk in each case optionally Substituted aryl, heteroaryl, aryla enyl, alkynyl, phenyl and phenylalkyl, lkyl and heteroarylalkyl and an optionally substituted 0033 Y' and Y are each independently C=O or S(O), amino group, 0034 m is 1, 2, 3 or 4, I0022 R is a radical from the group of hydrogen, in each I0035) R' is a radical from the group of hydrogen, alkyl, case optionally substituted alkyl, alkoxy, alkenyl and alky haloalkyl, cyano, cyanoalkyl, hydroxyalkyl, hydroxyl, nyl, in each case optionally Substituted cycloalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, cycloalkylalkyl and cycloalkenyl, in which the rings may cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkyl contain at least one heteroatom from the group of Sulphur, carbonyl and alkoxycarbonyl, oxygen (where oxygen atoms must not be immediately 10036) Y is a radical from the group of alkoxy, haloalkoxy, adjacent) and nitrogen, in each case optionally substituted alkylthio, haloalkylthio and NR'R' where R'' and R' aryl, heteroaryl, arylalkyl and heteroarylalkyl and an are each independently radicals from the group of hydro optionally Substituted amino group, gen, alkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, cyano, 0023 R and R may also form, together with the N- C cyanoalkyl, hydroxyl, alkoxy, haloalkoxy, hydroxyalkyl, (X) group to which they are bonded, a saturated or unsat alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, urated and optionally substituted 4- to 8-membered ring cyanoalkenyl, alkynyl, haloalkynyl,
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