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    • 专利摘要:
    The present invention is directed to novel 3-biphenyl-substituted, 3-substituted 4-ketoractams and -lactones of the general formula (I), to methods for their preparation and their use as pesticides and / or bactericides and / or herbicides. It is about: Where A, B, Q, G, W, X, Y and Z are as defined in the specification.
    公开号:KR20040058302A
    申请号:KR10-2004-7007676
    申请日:2002-11-18
    公开日:2004-07-03
    发明作者:피셔라이너；울만아스트리트；브레트슈나이더토마스；드레베스마르크빌헬름；에르델렌크리스토프；호이흐트디터；렉크만우도；쿠크카를-하인쯔；바헨도르프-노이만울리케
    申请人:바이엘 크롭사이언스 아게；
    IPC主号:
    专利说明:

    3-biphenyl-substituted-3-substituted-3-substituted-4-ketolactam and ketolactone and their utilization as pesticide}
    [1] The present invention relates to novel 3-biphenyl-substituted, 3-substituted 4-ketoractams and -lactones, methods and intermediates for the preparation thereof, and to their use as pesticides, microbicides and / or herbicides.
    [2] Certain phenyl-substituted 3-halo-4-ketoractams (JP-A-10-258 555) and phenyl-substituted 3-halo-4-ketolactones (JP-A-10-258 555) are acaricides It is already known to act as insecticide and / or herbicide.
    [3] However, the activity and activity spectrum of these compounds are not necessarily satisfactory, especially at low application rates and concentrations. In addition, the compatibility of these compounds with crops is not always satisfactory.
    [4] The present invention provides novel compounds of the general formula (I):
    [5]
    [6] Where
    [7] Q represents oxygen, sulfur or group N-D,
    [8] X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro, cyano or optionally substituted phenyl,
    [9] Y represents in each case optionally substituted aryl or hetaryl,
    [10] W and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano,
    [11] A represents hydrogen or, in each case, saturated or unsaturated cycloalkyl, optionally substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, or optionally at least one ring atom is replaced by a hetero atom and optionally substituted Or in each case optionally represents halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl,
    [12] B represents hydrogen, alkyl or alkoxyalkyl, or
    [13] A and B, together with the carbon atoms to which they are attached, represent a cycle, optionally containing at least one hetero atom, saturated or unsaturated, unsubstituted or substituted,
    [14] D represents hydrogen or alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, arylalkyl, aryl, het, wherein one or more ring members are optionally replaced by heteroatoms An optionally substituted radical selected from the group consisting of arylalkyl and hetaryl,
    [15] A and D together with the atoms to which they are attached represent a saturated or unsaturated ring in which the A, D moiety is unsubstituted or substituted and optionally contains at least one heteroatom,
    [16] G represents halogen or nitro.
    [17] In particular, the compounds of the general formula (I) may exist in geometric and / or optical isomers, or in mixtures of isomers of various compositions, which can be separated by conventional methods as necessary, depending on the kind of substituents. The present invention provides both pure isomers and isomer mixtures, methods for their preparation and uses, and compositions containing them. However, in the following, for the sake of convenience only the compounds of general formula (I) are always mentioned, which is intended to include both pure compounds and optionally mixtures in which isomer compounds are present in various proportions.
    [18] Including the meaning of Q, the following main structures (I-1) to (I-3) are formed:
    [19]
    [20]
    [21] Where
    [22] A, B, D, G, W, X, Y and Z are as defined above.
    [23] In addition, according to the present invention
    [24] (A) Compounds of formulas (I-1) to (I-3) may be prepared by the compounds of formulas (II-1) to (II-3) in the presence of a solvent and optionally in the presence of a free-radical initiator It has been found that it is obtained by reacting with a halogenating agent:
    [25]
    [26]
    [27] Where
    [28] A, B, Q, W, X, Y and Z are as defined above,
    [29] G represents halogen, preferably chlorine and bromine.
    [30] (B) Furthermore, the compounds of the general formulas (I-1) to (I-3) may be prepared by the compounds of the general formulas (II-1) to (II-3) with a nitrating agent, for example fuming nitric acid, in the presence of a solvent. It was found that it is obtained by reacting:
    [31]
    [32]
    [33] Where
    [34] A, B, Q, W, X, Y and Z are as defined above,
    [35] G represents nitro.
    [36] Compounds of the general formulas (II-1) to (II-3) required for the methods (A) and (B) are known compounds (see WO 99/43649, WO 99/48869, WO 99/55673), or It may be synthesized by the disclosed method:
    [37]
    [38] Where
    [39] A, B, Q, W, X, Y and Z are as defined above.
    [40] Suitable halogenating agents for method (A) are, for example, sulfuryl chloride, sulfuryl bromide, thionyl chloride, thionyl bromide, imides such as N-bromosuccinimide, N-chlorosuccinimide, Chlorosulfonic acid, and hypochlorite, for example t-butyl hypochlorite.
    [41] Nitrogenating agents suitable for process (B) are fuming nitric acid and also a "nitrated acid mixture".
    [42] It has also been found according to the invention that the novel compounds of general formula (I) show very good activity as pesticides, preferably insecticides, acaricides and / or fungicides and / or herbicides.
    [43] Formula (I) provides a general definition of a compound according to the invention. The range of preferred substituents or radicals given in the structural formulas mentioned above and hereafter is as follows:
    [44] Q preferably represents oxygen, sulfur or group N-D,
    [45] W preferably represents hydrogen, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy,
    [46] X preferably represents halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy or cyano, or optionally halogen- , C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -haloalkoxy-, nitro- or cyano-substituted phenyl ,
    [47] Y preferably represents one of the following radicals:
    [48]
    [49] V 1 is preferably hydrogen, halogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -Alkylsulfonyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, nitro or cyano or halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C Phenyl optionally mono- or disubstituted by 1- C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, nitro or cyano,
    [50] V 2 and V 3 independently of one another preferably represent hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy Indicate,
    [51] Z preferably represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, nitro or cyano,
    [52] A is preferably in each case optionally halogen-substituted C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, C 1 -C 10 -alkoxy-C 1 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl or C 1 -C 10 -alkylthio-C 1 -C 6 -alkyl or optionally one or two directly non-adjacent ring members are oxygen and / or C 3 -C 8 -cycloalkyl substituted by sulfur and optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted, in each case optionally halogen-, C 1- C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, cyano- or nitro-substituted phenyl or phenyl-C 1- C 6 -alkyl or, in the case of group (I-1), hydrogen when D is not hydrogen,
    [53] B preferably represents hydrogen, C 1 -C 12 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl,
    [54] A, B and the carbon atoms to which they are attached are preferably optionally substituted with one ring member by oxygen or sulfur and is C 1 -C 8 -alkyl, C 3 -C 10 -cycloalkyl, C 1 -C 6 -haloalkyl , C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, saturated C 3 -C 10 -cycloalkyl optionally substituted by halogen or phenyl or unsaturated C 5 -C 10 -cycloalkyl Or
    [55] A, B and the carbon atoms to which they are bonded are preferably further 5- to 5 by alkylenediyl groups optionally containing one or two directly non-contiguous oxygen and / or sulfur atoms, or together with the carbon atoms bonded thereto. C 3 -C 6 -cycloalkyl substituted by alkylenedioxyl or alkylenedithioyl group forming an 8-membered ring, or
    [56] A, B and the carbon atom to which they are bonded are preferably two substituents together with the carbon atom to which they are attached, in each case optionally C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy- or halogen-substituted and optionally one methylene group is replaced by oxygen or sulfur, C 2 -C 6 - alkanediyl, C 2 -C 6 - C 3 -C 8 alkane representing diendi yl-Al canned or C 4 -C 6 days -Cycloalkyl or C 5 -C 8 -cycloalkenyl,
    [57] D preferably represents hydrogen or, in each case, optionally halogen-substituted C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 1 -C 10- Alkoxy-C 2 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl or C 1 -C 10 -alkylthio-C 2 -C 8 -alkyl, or optionally one Ring members of are replaced by oxygen or sulfur and are optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkyl-substituted C 3 -C 8- Cycloalkyl or optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, cyano Or nitro-substituted phenyl;
    [58] A and D together represent preferably C 3 -C 6 -alkanediyl or C 3 -C 6 -alkenediyl, which in each case are optionally substituted and optionally one methylene group is replaced by oxygen or sulfur,
    [59] Possible substituents in each case are C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or additional C 3 -C 6 -alkanediyl groups,
    [60] G preferably represents chlorine, bromine or nitro.
    [61] In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
    [62] Q particularly preferably represents oxygen, sulfur or group N-D,
    [63] W particularly preferably represents hydrogen, chlorine, bromine or C 1 -C 4 -alkyl,
    [64] X particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or nitro,
    [65] Y is particularly preferably radical
    [66] Indicates
    [67] V 1 is particularly preferably hydrogen, fluorine, chlorine, bromine, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, nitro Or cyano, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, nitro or cya Phenyl optionally mono- or disubstituted by the furnace,
    [68] V 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy ,
    [69] Z particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkoxy,
    [70] A particularly preferably represents C 1 -C 10 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, which is optionally mono- to substituted by fluorine or chlorine, respectively, or optionally one ring member Represents C 3 -C 7 -cycloalkyl substituted by oxygen or sulfur and optionally mono- or di-substituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or each of fluorine, Phenyl or phenyl-C optionally mono- or disubstituted by chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy 1- C 2 -alkyl or, in the case of group (I-1), hydrogen when D is not hydrogen,
    [71] B particularly preferably represents hydrogen or C 1 -C 6 -alkyl,
    [72] A, B and the carbon atoms to which they are attached are particularly preferably optionally substituted with one ring member by oxygen or sulfur, C 1 -C 6 -alkyl, C 5 -C 6 -cycloalkyl, C 1 -C 3 —Haloalkyl, C 1 -C 6 -alkoxy, saturated C 3 -C 8 -cycloalkyl optionally mono- or disubstituted by phenyl, provided that D in group (I-1) is Hydrogen or C 1 -C 4 -alkyl,
    [73] D particularly preferably denotes C 1 -C 10 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 2 which represent hydrogen or are optionally mono- to substituted by fluorine or chlorine, respectively -C 4 -alkyl or C 1 -C 4 -alkylthio-C 2 -C 4 -alkyl, or optionally one methylene group is replaced by oxygen or sulfur and is fluorine, chlorine, C 1 -C 4 -alkyl C 3 -C 7 -cycloalkyl optionally substituted by C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkyl or fluorine, chlorine, bromine, C 1 -C 4 -alkyl Or phenyl optionally mono- or disubstituted by C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
    [74] A and D together represent particularly preferably C 3 -C 5 -alkanediyl, optionally substituted by oxygen or sulfur, optionally with one methylene group, where possible substituents are C 1 -C 4 -Alkyl,
    [75] G particularly preferably represents chlorine, bromine or nitro.
    [76] In the radical definitions mentioned as being particularly preferred, halogen denotes fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
    [77] Q very particularly preferably represents oxygen, sulfur or group N-D,
    [78] W very particularly preferably represents hydrogen, chlorine, methyl or ethyl,
    [79] X is very particularly preferably chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or Represents cyano,
    [80] Y is very particularly preferably radical
    [81] Indicates
    [82] V 1 is very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, methoxy, ethoxy, n-propoxy, iso Propoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano,
    [83] V 2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
    [84] Z very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl or methoxy,
    [85] A is very particularly preferably C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl or optionally C 3 -C 6 -wherein one ring member is replaced by oxygen or sulfur. Cycloalkyl or, in the case of group (I-1), hydrogen when D is not hydrogen,
    [86] B very particularly preferably represents hydrogen, methyl or ethyl, or
    [87] A, B and the carbon atoms to which they are attached are very particularly preferably optionally substituted with one ring member by oxygen or sulfur, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl , Saturated C 3 -C 8 -cycloalkyl optionally substituted by monofluoro, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, provided that D in group (I-1) represents hydrogen or C 1 -C 3 -alkyl,
    [88] Very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopentyl or cyclohexyl, more preferably hydrogen,
    [89] A and D together very particularly preferably represent C 3 -C 4 -alkanediyl, optionally substituted by one carbon atom and optionally substituted by oxygen or sulfur,
    [90] G very particularly preferably represents chlorine or nitro, more preferably chlorine.
    [91] W particularly preferably represents hydrogen, chlorine or methyl,
    [92] X particularly preferably represents chlorine, methyl or ethyl,
    [93] Y is particularly preferably radical
    [94] Indicates,
    [95] V 1 particularly preferably represents chlorine or methyl,
    [96] V 2 particularly preferably represents hydrogen or chlorine,
    [97] Z particularly preferably represents hydrogen or methyl,
    [98] A particularly preferably represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl (particularly methyl or isopropyl),
    [99] B particularly preferably represents methyl,
    [100] A, B and the carbon atoms to which they are attached are particularly preferably optionally substituted by one ring member by oxygen or sulfur, by methyl or in the case of C 6 -cycloalkyl also ethyl, n-propyl, isopropyl, n Saturated C 3 -C 8 optionally monosubstituted by butyl, isobutyl, t-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy For cycloalkyls (particularly for C 3- , C 5 -or C 6 -cycloalkyl, C 6 -cycloalkyl, optionally one ring atom is replaced by oxygen and methyl, ethyl, n-propyl, isopropyl, meso Optionally monosubstituted by oxy or ethoxy),
    [101] D particularly preferably represents hydrogen,
    [102] Particular preference is given to compounds of the general formula (I-1) in which G particularly preferably represents chlorine or nitro (particularly chlorine).
    [103] W particularly preferably represents hydrogen, chlorine or methyl (particularly hydrogen or methyl),
    [104] X particularly preferably represents chlorine, methyl or ethyl (particularly methyl or ethyl),
    [105] Y is particularly preferably radical
    [106]
    [107] (Especially,
    [108] Indicates,
    [109] V 1 particularly preferably represents chlorine, fluorine, cyano or methyl,
    [110] V 2 particularly preferably represents hydrogen or chlorine,
    [111] Z particularly preferably represents hydrogen or methyl,
    [112] A particularly preferably represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl (particularly methyl or isopropyl),
    [113] B particularly preferably represents methyl,
    [114] A, B and the carbon atoms to which they are attached are particularly preferably optionally substituted by one ring member by oxygen or sulfur, by methyl or in the case of C 6 -cycloalkyl also ethyl, n-propyl, isopropyl, n Saturated C 3 -C 8 optionally monosubstituted by butyl, isobutyl, t-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy For cycloalkyl (especially for C 5 -or C 6 -cycloalkyl, C 6 -cycloalkyl, optionally one ring atom is replaced by oxygen and optionally substituted by methyl, trifluoromethyl, methoxy or ethoxy Substituted),
    [115] Particular preference is given to compounds of the general formula (I-2) in which G particularly preferably represents chlorine.
    [116] W particularly preferably represents hydrogen,
    [117] X particularly preferably represents chlorine or methyl (particularly methyl),
    [118] Y is particularly preferably radical
    [119] Indicates,
    [120] Z particularly preferably represents hydrogen or methyl,
    [121] A, B and the carbon atoms to which they are attached are particularly preferably saturated C 5 -C 6 -cycloalkyl (particularly C 6 -cyclo) in which one ring member is replaced by oxygen and optionally substituted by methyl or methoxy Alkyl),
    [122] Particular preference is given to compounds of the general formula (I-3) in which G particularly preferably represents chlorine.
    [123] The above mentioned general or preferred range of radicals or descriptions can be combined with one another as desired, ie a combination between each range and a preferred range is possible. This also applies to the final product and, correspondingly, to precursors and intermediates.
    [124] In the present invention, preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as preferred (more preferred).
    [125] In the present invention, particular preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as being particularly preferred.
    [126] In the present invention, very particular preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as very particularly preferred.
    [127] Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can be as straight or branched as possible, including, for example, those bonded with heteroatoms such as in alkoxy.
    [128] Unless stated otherwise, optionally substituted radicals may be mono- or polysubstituted, and when polysubstituted, the substituents may be the same or different.
    [129] In addition to the compounds mentioned in the preparation examples, compounds of the general formula (I-1) may be specifically mentioned:
    [130]
    [131] Table 1 :
    [132] W = H; X = CH 3 ; V 1 = H; V 2 = H; Z = H.
    [133]
    [134]
    [135]
    [136]
    [137] TABLE 2 :
    [138] A, B and D are as defined in Table 1, respectively.
    [139] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = H; V 2 = H.
    [140] Table 3 :
    [141] A, B and D are as defined in Table 1, respectively.
    [142] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = H; V 2 = H.
    [143] Table 4 :
    [144] A, B and D are as defined in Table 1, respectively.
    [145] W = H; X = CH 3 ; Z = H; V 1 = 4-Cl; V 2 = H.
    [146] Table 5 :
    [147] A, B and D are as defined in Table 1, respectively.
    [148] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-Cl; V 2 = H.
    [149] Table 6 :
    [150] A, B and D are as defined in Table 1, respectively.
    [151] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-Cl; V 2 = H.
    [152] Table 7 :
    [153] A, B and D are as defined in Table 1, respectively.
    [154] W = H; X = CH 3 ; Z = H; V 1 = 3-Cl; V 2 = H.
    [155] Table 8 :
    [156] A, B and D are as defined in Table 1, respectively.
    [157] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = H.
    [158] Table 9 :
    [159] A, B and D are as defined in Table 1, respectively.
    [160] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = H.
    [161] Table 10 :
    [162] A, B and D are as defined in Table 1, respectively.
    [163] W = H; X = CH 3 ; Z = H; V 1 = 3-Cl; V 2 = 4-Cl.
    [164] Table 11 :
    [165] A, B and D are as defined in Table 1, respectively.
    [166] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = 4-Cl.
    [167] Table 12 :
    [168] A, B and D are as defined in Table 1, respectively.
    [169] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = 4-Cl.
    [170] Table 13 :
    [171] A, B and D are as defined in Table 1, respectively.
    [172] W = H; X = CH 3 ; Z = H; V 1 = 4-CF 3 ; V 2 = H.
    [173] Table 14 :
    [174] A, B and D are as defined in Table 1, respectively.
    [175] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CF 3 ; V 2 = H.
    [176] Table 15 :
    [177] A, B and D are as defined in Table 1, respectively.
    [178] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CF 3 ; V 2 = H.
    [179] Table 16 :
    [180] A, B and D are as defined in Table 1, respectively.
    [181] W = H; X = CH 3 ; Z = H; V 1 = 4-CH 3 ; V 2 = H.
    [182] Table 17 :
    [183] A, B and D are as defined in Table 1, respectively.
    [184] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CH 3 ; V 2 = H.
    [185] Table 18 :
    [186] A, B and D are as defined in Table 1, respectively.
    [187] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CH 3 ; V 2 = H.
    [188] Table 19 :
    [189] A, B and D are as defined in Table 1, respectively.
    [190] W = H; X = CH 3 ; Z = H; V 1 = 4-OCH 3 ; V 2 = H.
    [191] Table 20 :
    [192] A, B and D are as defined in Table 1, respectively.
    [193] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-OCH 3 ; V 2 = H.
    [194] Table 21 :
    [195] A, B and D are as defined in Table 1, respectively.
    [196] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-OCH 3 ; V 2 = H.
    [197] In addition to the compounds mentioned in the preparation examples, the following compounds of the general formula (I-2) may be specifically mentioned:
    [198]
    [199] Table 22 :
    [200] W = H; X = CH 3 ; Z = H; V 1 = H; V 2 = H.
    [201]
    [202]
    [203] Table 23 :
    [204] A and B are as defined in Table 22, respectively.
    [205] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = H; V 2 = H.
    [206] Table 24 :
    [207] A and B are as defined in Table 22, respectively.
    [208] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = H; V 2 = H.
    [209] Table 25 :
    [210] A and B are as defined in Table 22, respectively.
    [211] W = H; X = CH 3 ; Z = H; V 1 = 4-Cl; V 2 = H.
    [212] Table 26 :
    [213] A and B are as defined in Table 22, respectively.
    [214] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-Cl; V 2 = H.
    [215] Table 27 :
    [216] A and B are as defined in Table 22, respectively.
    [217] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-Cl; V 2 = H.
    [218] Table 28 :
    [219] A and B are as defined in Table 22, respectively.
    [220] W = H; X = CH 3 ; Z = H; V 1 = 3-Cl; V 2 = H.
    [221] Table 29 :
    [222] A and B are as defined in Table 22, respectively.
    [223] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = H.
    [224] Table 30 :
    [225] A and B are as defined in Table 22, respectively.
    [226] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = H.
    [227] Table 31 :
    [228] A and B are as defined in Table 22, respectively.
    [229] W = H; X = CH 3 ; Z = H; V 1 = 4-CF 3 ; V 2 = H.
    [230] Table 32 :
    [231] A and B are as defined in Table 22, respectively.
    [232] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CF 3 ; V 2 = H.
    [233] Table 33 :
    [234] A and B are as defined in Table 22, respectively.
    [235] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CF 3 ; V 2 = H.
    [236] Table 34 :
    [237] A and B are as defined in Table 22, respectively.
    [238] W = H; X = CH 3 ; Z = H; V 1 = 3-Cl; V 2 = 4-Cl.
    [239] Table 35 :
    [240] A and B are as defined in Table 22, respectively.
    [241] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = 4-Cl.
    [242] Table 36 :
    [243] A and B are as defined in Table 22, respectively.
    [244] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 3-Cl; V 2 = 4-Cl.
    [245] Table 37 :
    [246] A and B are as defined in Table 22, respectively.
    [247] W = H; X = CH 3 ; Z = H; V 1 = 4-CH 3 ; V 2 = H.
    [248] Table 38 :
    [249] A and B are as defined in Table 22, respectively.
    [250] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CH 3 ; V 2 = H.
    [251] Table 39 :
    [252] A and B are as defined in Table 22, respectively.
    [253] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-CH 3 ; V 2 = H.
    [254] Table 40 :
    [255] A and B are as defined in Table 22, respectively.
    [256] W = H; X = CH 3 ; Z = H; V 1 = 4-OCH 3 ; V 2 = H.
    [257] Table 41 :
    [258] A and B are as defined in Table 22, respectively.
    [259] W = H; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-OCH 3 ; V 2 = H.
    [260] Table 42 :
    [261] A and B are as defined in Table 22, respectively.
    [262] W = CH 3 ; X = CH 3 ; Z = 4-CH 3 ; V 1 = 4-OCH 3 ; V 2 = H.
    [263] According to method (A), 3-[(2-methyl-5-phenyl) phenyl] -5,5-pentamethylene-4-hydroxy-Δ 3 -pyrrolidin-2-one is used as starting material In the case, the process of the process according to the invention can be represented by the following scheme:
    [264]
    [265] When using 3-[(2-methyl-5- (4-chloro) phenyl) phenyl] -4-hydroxy-5,5-dimethyl-Δ 3 -furan-2-one according to method (B) The process of the process according to the invention can be represented by the following scheme:
    [266]
    [267] Process (A) is characterized in that A, B, Q, W, X, Y and Z are compounds of formula (II) as defined above in the presence of diluents and halogenating agents and optionally in the presence of free-radical initiators. It is characterized by reacting under. Suitable free-radical initiators are for example benzoyl peroxide or azobisisobutyronitrile.
    [268] Suitable diluents for use in process (A) according to the invention are all inert organic solvents. These include hydrocarbons such as benzene, toluene and xylene, ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, halogenated hydrocarbons such as dichloromethane, chloroform Preference is given to using carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene, and esters such as ethyl acetate.
    [269] Suitable halogenating agents for method (A) are, for example, sulfuryl chloride, thionyl chloride, thionyl bromide, imides such as N-bromosuccinimide, N-chlorosuccinimide, chlorosulfonic acid, and Hypochlorite, for example t-butyl hypochlorite.
    [270] When carrying out process (A) according to the invention, the reaction temperature can vary within a relatively wide range. Generally this process is carried out at temperatures between -40 and 150 ° C, preferably between 0 and 100 ° C.
    [271] Process (A) according to the invention is generally carried out under atmospheric pressure.
    [272] When carrying out process (A) according to the invention, the reaction components of the general formula (II) and the halogenating agents are generally used in approximately equimolar amounts. However, it is also possible to use one component or another component in a relative excess (maximum 3 moles).
    [273] Method (B) is characterized in that A, B, Q, W, X, Y and Z react the compound of formula (II) as defined above in the presence of a diluent and in the presence of a nitrating agent.
    [274] Suitable diluents for use in process (B) according to the invention are all inert organic solvents. Preference is given to using halogenated hydrocarbons such as methylene chloride, chloroform, dichlorobenzene and dichloroethane as these.
    [275] Suitable nitrating agents are "nitrogenated acids", preferably fuming nitric acid.
    [276] When carrying out process (B) according to the invention, the reaction temperature can vary within a relatively wide range. Generally this process is carried out at temperatures between -50 and 150 ° C, preferably between 0 and 80 ° C.
    [277] Process (B) according to the invention is generally carried out under atmospheric pressure.
    [278] When carrying out process (B) according to the invention, the reaction components of the general formula (II) and the nitrating agent are generally used in approximately equimolar amounts. However, it is also possible to use one component or another component in a relative excess (maximum 5 moles).
    [279] The active compounds are used in animal pests, in particular insects, arachnids, which are encountered in the protection of plants and plant organs, in increasing yields, in improving the quality of harvest products, and in the protection and hygiene of agriculture, forestry, garden and leisure facilities, storage products and materials. And nematode control, having good plant tolerability, acceptable levels of warm-blooded animal toxicity and good environmental friendliness. They can preferably also be used as crop protection agents. They are active against normal sensitive and resistant species and all or some stages of development. The pests mentioned above include:
    [280] The order of Isopoda , for example Oniscus asellus , Armadillidium vulgare and Porcellio scaber .
    [281] Millipedes (Diplopoda) tree, for example Blast niul loose obtain Tula tooth (Blaniulus guttulatus).
    [282] From the genus Chilopoda , for example Geophilus carpophagus and Scutigera spec .
    [283] From the order of Symphyla , for example Scutigerella immaculata .
    [284] Thysanura , for example Lepisma saccharina .
    [285] From the order of Collembola , for example Onychiurus armatus .
    [286] Orthoptera , for example, Acheta domesticus , Gryllotalpa spp. , Locusta migratoria migratorioides , melanoplus ( Melanoplus spp.) And Schistocerca gregaria .
    [287] From the tree of Blattaria , for example Blatta orientalis , Periplaneta americana , Leucophaea maderae , Blattella germanica .
    [288] Dermaptera , for example Forficula auricularia .
    [289] Termite Isoptera , for example Reticulitermes spp .
    [290] Phthiraptera , for example Pediculus humanus corporis , Haematopinus spp ., Linognathus spp ., Trichodectes spp. .) And damalinia spp .
    [291] Thysanoptera order, for example Hercinothrips femoralis , Thrips tabaci , Thrips palmi and Frankliniella accidentalis ).
    [292] From the order of Heteroptera , for example Eurygaster spp ., Dysdercus intermedius , Piesma quadrata , Cimex lectularius , Rodney Rhodnius prolixus and Triatoma spp .
    [293] Cicadas (Homoptera) tree, for example, waters right Death in Brassica (Aleurodes brassicae), bemi cyano other dedicate (Bemisia tabaci), the tree Valley right des bar Fora Rio room (Trialeurodes vaporariorum), Apis notice blood (Aphis gossypii), the breather Vico Rhine Brassica (Brevicoryne brassicae), the creep Tommy juice Leavis (Cryptomyzus ribis), Apis wave bar (Aphis fabae), Apis breech (Aphis pomi), Erie O Soma Raney gerum (Eriosoma lanigerum), hyaluronic rope Teruel's Arun Dinis ( Hyalopterus arundinis ), Phylloxera vastatrix , Pemphigus spp. , Macrosiphum avenae , Myzus spp ., Phorodon humulley humuli), a Palo sipum Fadi (Rhopalosiphum padi), empo Empoasca (Asuka kind spp.), yusel lease Biloba tooth (Euscelis bilobatus), four Forte Athletics new Sancti Joseph's (Nephotettix cincticeps), Recaro nium corset you (Lecanium cor ni), the poinsettia Ole Ah between (Saissetia oleae), Lao del Parks Austria Tel Ruth (Laodelphax striatellus), Neela Parque Bata Lou Regensburg (Nilaparvata lugens), Oh sludge de Ella Augusta is T (Aonidiella aurantii), Oh Speedy Aspidiotus hederae , Pseudococcus spp . And Psylla spp .
    [294] Lepidoptera , for example Pectinophora gossypiella , Bupalus piniarius , Cheimatobia brumata , Lithocolletis blancardella , Hyponomeuta padella , Plutella x ylostella , Malacosoma neustria , Euproctis chrysorrhoea , Lymantria spp. ), part Kula matrix Tour Barry Ella (Bucculatrix thurberiella), Philo greatest seutiseu sheet mozzarella (Phyllocnistis citrella), Agrobacterium-Tees species (Agrotis spp.), six pediatric species (Euxoa spp.), Pell Tia species (Feltia spp.), Earias insulana , Heliothis spp ., Mamestra brassicae , Panolis flammea , Spodoptera sp p .), Trichoplusia ni , Carpocapsa pomonella , Pieris spp. , Chilo spp ., Pyrausta nubilalis , Ephestia kuehniella , Galleria mellonella , Tineola bisselliella , Tinea pellionella , Hofmannophila pseudospretella , Cacoecia podana , Capua reticulana , Choristoneura fumiferana , Clysia ambiguella , Homona magnanima ), Tortrix viridana , Cnaphalocerus spp . And Oulema oryzae .
    [295] Coleoptera , for example, Anobium punctatum , Rhizopertha dominica , Bruchidius obtectus , Acanthoscelides obtectus , Hylotrupes bajulus , Agelastica alni , Leptinotarsa decemlineata , Phaedon cochleariae , Diabrotica spp ), peusil Rio des Creative sose Palacio (Psylliodes chrysocephala), epilra keuna Bari Betsy's (Epilachna varivestis), Ato Maria kinds (Atomaria spp.), duck chair Phil Ruth repairs namen system (Oryzaephilus surinamensis), St labor's servants (Anthonomus spp.), Citrus peel loose species (Sitophilus spp.), cut out ot kusu sulka tooth (Otiorrhynchus sulcatus), poly Cosmo test sorbitan di Douce (Cosmopolites sordidus), establish Torin Scotland know Millie's (Ceuthorrhynchus assimilis), Hebrews Blow Force Galactica (Hypera postica), no scalpel test species (Dermestes spp.), Tree logo Dumaguete species (Trogoderma spp.), No trail pandanus species (Anthrenus spp.), Oh ride Attagenus spp ., Lyctus spp ., Meligethes aeneus , Ptinus spp ., Niptus hololeucus , Gibiumuf Gibbium psylloides , Tribolium spp ., Tenebrio molitor , Agriotes spp ., Conoderus spp ., Melonta Melonta ( Melolontha melolontha ), Amphimallon solstitialis , Costelytra zealandica and Lissorhoptus oryzophilus .
    [296] Hymenopera species, for example Diprion spp ., Hoplocampa spp ., Lasius spp ., Monomorium pharaonis and Vespa species Vespa spp .
    [297] Diptera , for example Aedes spp ., Anopheles spp ., Culex spp ., Drosophila melanogaster , Musca species. Musca spp .), Fannia spp ., Calliphora erythrocephala , Lucilia spp ., Chrysomyia spp ., Cuterebra spp . ), Gastrophilus spp ., Hyppobosca spp ., Stomoxys spp ., Oestrus spp ., Hypoderma spp . , Tabanus spp. , Tannia spp ., Bibio hortulanus , Oscinella frit , Phorbia spp ., Pegomia hyosquiami ( Pegomyia hyoscyami ), Ceratitis capitata , Dacus oleae , Tifula paludosa Tipula paludosa ), Hylemyia spp . And Liriomyza spp .
    [298] From the order of Siphonaptera , for example Xenopsylla cheopis and Ceratophyllus spp .
    [299] Arachnida , for example, Scorpio maurus , Latrodectus mactans , Acarus siro , Argas spp ., Ornitodoros species (Ornithodoros spp.), der Mani in Sousse Galina (Dermanyssus gallinae), Erie ohpieseu Leavis (Eriophyes ribis), Philo Coptic doubles Olay Bora (Phyllocoptruta oleivora), bupil Ruth species (Boophilus spp.), Lippi three Palouse species (Rhipicephalus spp ., Amblyomma spp. , Hyalomma spp ., Ixodes spp ., Psoroptes spp ., Chorioptes spp. , Sarcoptes spp ., Tarsonemus spp ., Bryobia praetiosa , Panonychus spp ., Tetranychus spp. ), hemi other Sone mousse species (Hemitarsonemus spp.) and breather bipal crispus species (Brev ipalpus spp .).
    [300] Plant parasitic nematodes include, for example, Pratylenchus spp ., Radopholus similis , Ditylenchus dipsaci , Tylenchulus semipenetrans . , Heterodera spp ., Globodera spp ., Meloidogyne spp ., Apelenchoides spp ., Longidorus spp . , Xiphinema spp. , Trichodorus spp . And Bursaphelenchus spp .
    [301] If desired, the compounds according to the invention can also be used as herbicides or microbiocides, for example fungicides, antimicrobials and bactericides, when used in certain concentrations or application rates. If desired, they can also be used as intermediates or precursors for synthesizing other active compounds.
    [302] All plants and plant parts can be treated according to the invention. Plant is to be understood here as meaning all plants and plant populations, such as desired or unwanted wild plants or crops (including naturally occurring crops). Crops include plant varieties and transgenic plants that may or may not be protected by the rights of plant breeders, by conventional breeding and optimization methods, by biotechnology and recombinant methods, or by combining these methods It may be a plant obtainable by. Plant part means all above-ground and underground parts and organs of the plant, such as, for example, shoots, leaves, flowers, and roots, for example leaves, needles, stalks, stems, flowers, Fruits, fruits, seeds, roots, tubers and rhizomes may be mentioned. Plant parts also include harvesting materials, and nutritional and reproductive materials such as seedlings, tubers, rhizomes, cuttings and seeds.
    [303] Treatment of plants and plant parts with the active compounds according to the invention is also carried out in accordance with conventional processing methods, for example by dipping, spraying, evaporating, spraying, spraying, applying, injecting, in the case of propagating materials, in particular seed It is carried out by applying one or multilayer coatings directly or by acting the compound on its surroundings, environment or storage space.
    [304] The active compounds according to the invention can be prepared in the form of solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic substances in which the active compound has been injected, and microcapsules in polymers. It can be converted to conventional formulations such as.
    [305] These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents. .
    [306] If the extender used is water, it is also possible to use organic solvents, for example as auxiliary solvents. Primarily suitable liquid solvents are aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils. Strong aliphatic hydrocarbons such as aliphatic hydrocarbons, butanol or glycols and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide and water.
    [307] Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as solid silica, alumina and silicates. Suitable granular solid carriers are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, or synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , Arylsulfonates or protein hydrolysates. Suitable dispersants are for example lignin-sulfite waste liquors and methylcellulose.
    [308] Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used for Other possible additives are mineral and vegetable oils.
    [309] Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc Micronutrients can be used.
    [310] In general, the formulation contains 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.
    [311] The active compounds according to the invention can be used on their own or in mixtures with known fungicides, fungicides, acaricides, nematicides or insecticides in order to increase the activity spectrum or to prevent resistance from occurring. . In many cases a synergistic effect is obtained, ie the efficiency of the mixture is greater than that of the individual components.
    [312] Examples of suitable co-components in the mixture include the following compounds:
    [313] Fungicides:
    [314] Aldimorph, Ampropyl Force, Ampropyl Force-Potassium, Andoprim, Anilazine, Azaconazole, Azoxystrobin,
    [315] Benalacyl, Benodanil, Benomyl, Benzamacryl, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, Buptrimate, Butio Bait,
    [316] Calcium Polysulfide, Capsaicin, Captapol, Captan, Carbendazim, Carboxin, Carbon, Quinomethionate, Clobenthiazone, Chlorfenazole, Chloronev, Chloropicrine, Chlothalonil, Clozolinate, Chlozila Cones, cupraneb, cymoxanyl, cyproconazole, cyprodinyl, cypropuram,
    [317] Debaccarb, dichlorophene, diclobutrazole, diclofloanid, diclomezin, dichloran, dietofencarb, difenokonazole, dimethymolol, dimethomorph, dinicoazole, dinicoazole- M, dinocap, diphenylamine, dipyrithione, dietalifoss, dithianon, dodemorph, dodine, drazoxolone,
    [318] Edifene Force, Epoxyconazole, Etaconazole, Ethirimol, Etridiazole,
    [319] Sofasadon, phenafanil, phenarimol, fenbuconazole, fenfuram, phenytropane, fenpiclonyl, phenpropidine, fenpropormorph, fentin acetate, fentin hydroxide, ferbam, perimzone, flua Gina, flumetober, fluoromid, fluquinconazole, fluprimidol, flusilazole, flusulfamid, flutolanil, flutriafol, polpet, pocetyl-aluminum, pocetyl-sodium, phthalide, Fuberidazole, furalacyl, furametpyr, furcarbonyl, furconazole, furconazole-cis, purmecyclox,
    [320] Guazatin,
    [321] Hexachlorobenzene, hexaconazole, hymexazole,
    [322] Imazalyl, imibenconazole, iminottadine, iminottadine albesylate, iminottadine triacetate, iodocarb, ifconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, iso Ballet,
    [323] Kasugamycin, cresoxime-methyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures,
    [324] Mancoper, Mancozeb, Manev, Meperimzone, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metomeclam, Metsulfobox, Mildiomycin , Michaelrobutanyl, michaelrozoline,
    [325] Nickel dimethyldithiocarbamate, nitrotal-isopropyl, noarimol,
    [326] Opuras, oxadixyl, oxamocarb, oxolinic acid, oxycarboxime, oxypentin,
    [327] Paclobutrazole, pepurazoate, fenconazole, penicuron, phosphodiphene, picoxystrovin, fimaricin, piperaline, polyoxine, polyoxolin, provenazole, prochloraz, procymidone, pro Pamocarb, propanosine-sodium, propiconazole, propineb, pyraclostrobin, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxyfur,
    [328] Quinconazole, quintozen (PCNB),
    [329] Sulfur and sulfur preparations,
    [330] Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl , Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, triclamid, tricyclazole, tridemorph, trixystrobin, triflumizol, tripolin, tritico Nazol,
    [331] Uniconazole,
    [332] Validamycin A, vinclozoline, viniconazole,
    [333] Zarylamide, Genev, Zara, and also
    [334] Dagger G,
    [335] OK-8705,
    [336] OK-8801,
    [337] α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
    [338] α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,
    [339] α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,
    [340] α- (5-methyl-1,3-dioxan-5-yl) -β-[[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazole-1-ethanol ,
    [341] (5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
    [342] (E) -α- (methoxyimino) -N-methyl-2-phenoxyphenylacetamide,
    [343] 1-isopropyl {2-methyl-1-[[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamate,
    [344] 1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) ethanone-O- (phenylmethyl) -oxime,
    [345] 1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
    [346] 1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
    [347] 1-[(diiodomethyl) sulfonyl] -4-methylbenzene,
    [348] 1-[[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
    [349] 1-[[2- (4-chlorophenyl) -3-phenyloxyranyl] methyl] -1 H-1,2,4-triazole,
    [350] 1- [1- [2-[(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1 H-imidazole,
    [351] 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
    [352] 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
    [353] 2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide,
    [354] 2,6-dichloro-5- (methylthio) -4-pyrimidinylthiocyanate,
    [355] 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
    [356] 2,6-dichloro-N-[[4- (trifluoromethyl) phenyl] methyl] benzamide,
    [357] 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
    [358] 2-[(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
    [359] 2-[[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4-methoxy-1 H-pyrrolo [ 2,3-d] pyrimidine-5-carbonitrile,
    [360] 2-aminobutane,
    [361] 2-bromo-2- (bromomethyl) pentanedinitrile,
    [362] 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,
    [363] 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
    [364] 2-phenylphenol (OPP),
    [365] 3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
    [366] 3,5-dichloro-N- [cyano-[(1-methyl-2-propynyl) oxy] methyl] benzamide,
    [367] 3- (1,1-dimethylpropyl) -1-oxo-1H-indene-2-carbonitrile,
    [368] 3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
    [369] 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,
    [370] 4-methyltetrazolo [1,5-a] quinazolin-5 (4H) -one,
    [371] 8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4,5] decan-2-methanamine,
    [372] 8-hydroxyquinoline sulfate,
    [373] 9H-xanthene-2-[(phenylamino) carbonyl] -9-carboxylic acid hydrazide,
    [374] Bis- (1-methylethyl) -3-methyl-4-[(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,
    [375] Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol,
    [376] Cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,
    [377] Ethyl [(4-chlorophenyl) azo] cyanoacetate,
    [378] Potassium bicarbonate,
    [379] Methanetetrathiol-sodium salt,
    [380] Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
    [381] Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alanineate,
    [382] Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alanineate,
    [383] N- (2,3-dichloro-4-hydroxyphenyl) -1-methylcyclohexanecarboxamide,
    [384] N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
    [385] N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
    [386] N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitrobenzenesulfonamide,
    [387] N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
    [388] N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
    [389] N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,
    [390] N- (6-methoxy) -3-pyridinylcyclopropanecarboxamide,
    [391] N- [2,2,2-trichloro-1-[(chloroacetyl) amino] ethyl] benzamide,
    [392] N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymethaneimideamide,
    [393] N-formyl-N-hydroxy-DL-alanine-sodium salt,
    [394] O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate,
    [395] O-methyl S-phenyl phenylpropylphosphoramidothioate,
    [396] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,
    [397] Spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran-3'-one,
    [398] 4-[(3,4-dimethoxyphenyl) -3- (4-fluorophenyl) acryloyl] morpholine.
    [399] disinfectant:
    [400] Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.
    [401] Pesticides / Acaricides / Nematicides:
    [402] Abamectin, Acetate, Acetamiprid, Acrinatrin, Alanicarb, Aldicarb, Aldoxicarb, Alphacypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azameti Phos, azine force A, azine force M, azocyclotin,
    [403] Bacillus popiliae, Bacillus sp. Erytheus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Buberia Bassiana, Buberia Tenella, Bendiocab, Benfuracab, Bensultop, Benzosimate, Beta cyflutrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiophos, butocarboxime, butyl Pyridaben,
    [404] Cadusafos, cabaril, cabofuran, cabofennotion, cabosulphan, cartop, chloretocarb, chlorethoxy force, chlorfenapyr, chlorfenbinfos, chlorfluazuron, chlormephos, chlorpyrufos, chlor Pyriphos M, clovapotrin, chromafenozide, cis-resmethrin, cispermethrin, clocitrin, clotocarb, clofentezin, clothianidine, cyanophosph, cycloprene, cycloprotrin, Cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
    [405] Deltamethrin, Demethone M, Demethone S, Demethone-S-methyl, Diapentiourn, Diazinon, Dichlorvos, Dicopol, Diflubenzuron, Dimethoate, Dimethylbinfoss, Dinetopuran, Dio Phenolane, disulfotone, docusat-sodium, dofenapain,
    [406] Eflusilanate, Emamectin, Empentrin, Endosulfane, Entomorphora species (spp.), Espenalerate, Ethiophencarb, Ethion, Ethiprolol, Etopropos, Etofenprox, Etoxazole, Eth Lymphos,
    [407] Phenamifos, phenaquinone, fenbutatin oxide, phenythrothione, phenothiocarb, phenoxa cream, phenoxycarb, phenpropatrine, fenpyrad, phenpyrithine, fenpyroximate, pentian, fenvalle Latex, fipronil, fluazinam, fluazuron, flubrocitinate, flucycloxanthone, flucytinate, flufenoxuron, flumethrin, flupyrazophos, flutensin, fluvalinate , Phonophos, phosphmethylene, phosphthiazate, pufenfenrox, furathiocarb,
    [408] Granulosis Viruses,
    [409] Halofenozide, HCH, heptenophos, hexaflumuron, hexiaxose, hydroprene,
    [410] Imidacloprid, indoxacarb, isazofoss, isofenfoss, isoxation, ivermectin,
    [411] Nuclea polyhedrosis virus,
    [412] Lambda-cyhalothrin, lufenuron,
    [413] Malathion, Mecarbam, Metaldehyde, Metamidophos, Metadium Anisoplier, Metadium Flavoviride, Metidathione, Methiocarb, Matoprene, Methomil, Methoxyphenozide, Metolcarb, methoxadiazone, mevinforce, milbemectin, milbemycin, monochromophos,
    [414] Nalred, nitenpyram, nithiazine, novaluron,
    [415] Ometoate, oxamyl, oxydemethone M,
    [416] Paesilomyses pumosorusus, parathion A, parathion M, permethrin, pentoate, forate, posalon, phosphmet, phosphamidone, bombardment, pyrimicab, pyrimifos A, pyrimifos M, Propenophos, promecarb, propargite, propoxur, prothiophos, protoate, pymetrozine, pyraclophos, pyresmethrin, pyrethrum, pyridaben, pyridation, pyrimidipene, pyri Proxy Pen,
    [417] Quinal Force,
    [418] Ribavirin,
    [419] Salitione, cebufoss, silafluorophene, spinosad, spirodiclofen, sulfotep, sulfpropos,
    [420] Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupyrimifos, Teflubenzuron, Tefluthrin, Temephos, Temivinforce, Terbufos, Tetrachlorbinfos, Tetradipon, Teta-Sai Permethrin, thiamethoxam, tiacloprid, thiapronyl, thiatrifoss, thiocyclam hydrogen oxalate, thiodicarb, thiophanox, turingiencin, tralositerin, tralomethrin, triarate , Triamate, triazofoss, triazonone, triclofenidine, trichlorphone, triple lumuron, trimetacarb,
    [421] Amidothione, vaniliprole, vertilium recany,
    [422] YI 5302,
    [423] Zeta-cypermethrin, zolapropos,
    [424] (1R-cis)-[5- (phenylmethyl) -3-furanyl] methyl 3-[(dihydro-2-oxo-3 (2H) -furanilidene) methyl] -2,2-dimethylcyclopropane Carboxylate,
    [425] (3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,
    [426] 1-[(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) -imine,
    [427] 2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole,
    [428] 2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione,
    [429] 2-chloro-N-[[[4- (1-phenylethoxy) phenyl] amino] carbonyl] benzamide,
    [430] 2-chloro-N-[[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide,
    [431] 3-methylphenyl propylcarbamate,
    [432] 4- [4- (4-ethoxyphenyl) -4-methylphenyl] -1-fluoro-2-phenoxybenzene,
    [433] 4-chloro-2- (1,1-dimethylethyl) -5-[[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone,
    [434] 4-chloro-2- (2-chloro-2-methylpropyl) -5-[(6-iodo-3-pyridinyl) methoxy] -3 (2H) -pyridazinone,
    [435] 4-chloro-5-[(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone,
    [436] Bacillus thuringiensis strain EG-2348,
    [437] 2-benzoyl-1- (1,1-dimethylethyl) hydrazinobenzoic acid,
    [438] 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl butanoate,
    [439] [3-[(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] cyanamide,
    [440] Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde,
    [441] Ethyl [2-[[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate,
    [442] N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine,
    [443] N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,
    [444] N-[(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitroguanidine,
    [445] N-methyl-N '-(1-methyl-2-propenyl) -1,2-hydrazinedicarbothioamide,
    [446] N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide,
    [447] O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate,
    [448] N-cyanomethyl-4-trifluoromethylnicotinamide,
    [449] 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxy] benzene.
    [450] It is also possible to mix with other known active compounds, for example herbicides, fertilizers and growth regulators, safeners or signaling substances.
    [451] When used as insecticides, the active compounds according to the invention may also be present in their commercially available formulations and in the use forms prepared from these formulations as a mixture with synergists. Synergists are compounds that increase the action of the active compound without the need for the synergist added itself to be activated.
    [452] When used as insecticides, the active compounds according to the invention are prepared from their commercially available preparations and from these preparations as mixtures with inhibitors which reduce the degradation of the active compounds after use in the vicinity of plants, the surface of plant parts or plant tissues. May be present in the intended use form.
    [453] The active compound content of the use forms prepared from commercially available formulations can vary within wide ranges. The active compound concentration of the use forms is 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.
    [454] The compound is used in a conventional manner suitable for the use form.
    [455] When used in hygienic pests and stored product pests, the active compounds have the property of exhibiting excellent residual action on wood and clay and excellent stability against alkalis on lime substrates.
    [456] As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant varieties, or plant species and plant varieties obtained by conventional biological breeding methods such as hybrid breeding or protoplast fusion, and portions thereof are treated. In another preferred embodiment, transgenic plants and plant varieties (genetically modified organisms) obtained by genetic engineering methods, together with conventional methods, where appropriate, and portions thereof, are treated. The terms "part", "part of the plant" or "plant part" are described above.
    [457] Particularly preferably, plants of the plant variety which are commercially available or in each case are treated according to the invention. Plant varieties are to be understood as plants having new properties ("characteristics") generated by conventional cultivation techniques, mutagenesis or recombinant DNA techniques. These may be of cultivar, biotype or genotype.
    [458] Depending on the plant species or plant variety, their location and growing conditions (soil, climate, growing season, nutrients), an additive ("raising") effect may also be produced by treatment according to the invention. Thus, for example, reduction in the application rate of the materials and compositions used according to the invention and / or broadening the activity spectrum and / or increasing activity, improving plant growth, increasing hot or cold resistance, drought, or water or soil salinity Effects such as increased resistance to plants, increased flowering, ease of harvest, increased maturity, increased yields, improved quality and / or nutritional value of the harvested product, and improved storage stability and / or processability of the harvested product are beyond what is actually expected. May appear.
    [459] Transgenic plants or plant varieties (ie, those obtained genetically) which are preferably treated according to the invention are those which accept a genetic material that confers beneficial properties (“characteristics”) that are particularly advantageous for these plants upon genetic modification. Include. Examples of these properties include improved plant growth, increased high or low temperature resistance, drought, or increased resistance to water or soil salinity, increased flowering, ease of harvest, increased maturity, increased yields, improved quality of harvested products and / or nutritional value. Increase and storage stability and / or treatability of the harvested product are included. Further particularly notable examples of such properties include increased plant defense against animal and microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and also increased plant resistance to certain herbicidally active compounds. Examples of transgenic plants may include important crops, such as cereals (wheat, rice), corn, soybeans, potatoes, tobacco, cotton, oilseed rape, and also fruit plants (opening apples, pears, citrus fruits and grape fruits). Of particular interest are corn, soybeans, potatoes, cotton, tobacco and oilseed rape. Highlighted properties are in particular genetic material derived from toxins formed in plants, in particular Bacillus thuringiensis (eg genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c) , Cry2Ab, Cry3Bb and CryIF, and combinations thereof), increasing plant defense against insects, arachnids, nematodes, slugs, and snails due to toxins formed in plants (hereinafter referred to as "Bt plants"). Also of particular emphasis are the increased plant defenses against fungi, bacteria and viruses due to systemically acquired resistance (SAR), cystemine, phytoalexin, eliminators and resistance genes and correspondingly expressed proteins and toxins. to be. Particularly emphasized properties are also the increased tolerance of plants to certain herbicidally active compounds such as imidazolinone, sulfonylurea, glyphosate or phosphinothricin (eg the "PAT" gene). Genes that confer the desired properties of interest can also be present in a transgenic combination in a transgenic plant. Examples of "Bt plants" include YIELD GARD R (e.g. corn, cotton, soybean), KnockOut R (e.g. corn), StarLink R (e.g. corn), Bollgard R (e.g. cotton), Nucotn R (e.g. cotton) And corn varieties, cotton varieties, soybean varieties and potato varieties available under the name NewLeaf R (eg potatoes). Examples of herbicide-tolerant plants include Roundup Ready R (glyphosate tolerant, eg corn, cotton, soybean), Liberty Link R (phosphinothricin tolerant, e.g. oilseed rape), IMI R (imidazolinone tolerant) And corn varieties, cotton varieties and soybean varieties available under the trade name STS R (sulfonylurea tolerant, eg maize). Examples of herbicide-tolerant plants (plants bred by conventional methods for herbicide tolerability) may also be mentioned varieties sold under the name Clearfield R (eg corn). Of course, the above description also applies to plant varieties which are to be developed and / or marketed in the future, which have the above-mentioned characteristics or where the genetic characteristics are still left to be developed.
    [460] The plants listed can be treated in a particularly advantageous manner according to the invention using the compounds of the general formula (I) according to the invention or mixtures of the active compounds. The preferred ranges mentioned above for these active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
    [461] The active compounds according to the invention are not only plant pests, sanitary pests and stored product pests, but also animal parasites (in vitro parasites) in the field of veterinary medicine, for example, hard mites, soft mites, scabies mites, harvest mites, flies ( Stinging and sucking), parasitic fly larvae, teeth, hairs, algae and fleas. These parasites include:
    [462] Anoplurida species, for example Haematopinus spp ., Linognathus spp ., Pediculus spp ., Pthirus spp ., And sole Novotes spp .
    [463] Hairs (Mallophagida) neck and arm assembly Serena (Amblycerina) and yiseukeu furnace Serena (Ischnocerina) suborder, such as tree Agate phone species (Trimenopon spp.), Agate phone species (Menopon spp.), Trinoton spp (teurino tone species. ), Bovicola spp ., Werneckiella spp ., Lepikentron spp ., Damalina spp ., Trichodectes spp ., And Felicola spp .
    [464] Diptera and Nematocerina and Brachycerina subfamily, for example Aedes spp ., Anopheles spp ., Culex spp ., simul Solarium species (Simulium spp.), Yushi water Solarium species (Eusimulium spp.), play bottoming mousse species (Phlebotomus spp.), Lucho Mia species (Lutzomyia spp.), Cooley Koh des species (Culicoides spp.), chestnut Thorpe Crysops spp ., Hybomitra spp ., Atylotus spp ., Tabanus spp ., Haematopota spp ., Filippomia spp . Philipomyia spp. ), Braula spp ., Musca spp ., Hydrotaea spp ., Stomoxys spp ., Haematobia spp . , Morelia species (Morellia spp.), plates Chania species (Fannia spp.), Gloucestershire Sinai species (Glossina spp.), Carly Fora species (Calliphora spp.), rusilriah species (Luci lia spp .), Chrysomyia spp ., Wolhlfahrtia spp. , Sarcophaga spp ., Oestrus spp ., Hypoderma spp . ), Gasterophilus spp ., Hyppobosca spp ., Lipoptena spp . And Melophagus spp .
    [465] Siphonapterida species, for example Pulex spp ., Ctenocephalides spp ., Xenopsylla spp . And Ceratophyllus spp .
    [466] From the order of Heteropterida , for example Cimex spp ., Triatoma spp ., Rhodnius spp . And Panstrongylus spp .
    [467] Blattarida neck, for example Blatta orientalis , Periplaneta americana , Blatta germanica and Supella spp .
    [468] Mites (Acaria (Acarida)) subclass and meta- and meso stigmasterol other - (. Ornithodorus spp) (Meta and Mesostigmata) tree, for example, are the gas species (. Argas spp), ornithine Todo loose species, auto Flavian species (Otobius spp.), Rhodes ikso species (Ixodes spp.), cancer Bulletin Mama species (Amblyo㎜a spp.), Ruth bupil species (Boophilus spp.), der Do centaur species (Dermancentor spp.), under the village killed lease species ( Haemaphysalis spp.), kind of hyaluronic romma (Hyalo㎜a spp.), Lippi Palouse three species (Rhipicephalus spp.), der Mani Seuss species Dermanyssus (spp.), Raillietia (Tia Riley species spp.), Seuss pneumoniae species ( Pneumonyssus spp .), Sternostoma spp . And Varroa spp .
    [469] Actinedida ( Prostigmata ) and Acaridida ( Astigmata ) necks, for example Acarapis spp ., Cheyletiella spp . ), Ornithocheyletia spp ., Myobia spp ., Psorergates spp ., Demodex spp ., Trombicula spp . , Listrophorus spp ., Acarus spp ., Tyrophagus spp ., Caloglyphus spp ., Hypodectes spp . , Pterolichus spp. , Psoroptes spp. , Chorioptes spp ., Otodectes spp ., Sarcoptes spp . dress species in Noto (Notoedres spp.), shown immense Cope test species (Knemidocoptes spp.), Citrus di test species (Cytodites spp.) and Minoh off test species (Laminosioptes spp.).
    [470] The active compounds of general formula (I) according to the invention can also be used for agricultural productive livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, and others. It is suitable for controlling arthropods that invade pets such as dogs, cats, birds in bird cages and fish tanks, and so-called laboratory animals such as hamsters, guinea pigs, rats and mice. By controlling these arthropods, death and yield reduction (in meat, milk, wool, leather, eggs, honey, etc.) are reduced, and thus more economical and convenient animal management is possible by using the active compounds according to the present invention.
    [471] The active compounds according to the invention are administered parenterally in the field of veterinary medicine, for example by intestinal administration in the form of tablets, capsules, beverages, potions, granules, pastes, pills, feed methods and suppositories, eg By injection (intramuscular, subcutaneous, intravenous and intraperitoneal, etc.), by insertion, by intranasal administration, for example by dipping or bathing, spraying, swelling and dropping, washing and spraying Or in the form of shaped articles containing the active compounds, for example in the form of necklaces, ear marks, tail marks, leg bands, bridles, indicators, etc., in a known manner by transdermal use.
    [472] For use in livestock, poultry, pets and the like, the active compounds of formula (I) are either directly or as preparations (e.g. powders, emulsions, free flowing compositions) containing the active compounds in an amount of 1 to 80% by weight. It can be used diluted 100 to 10,000 times, or can be used in the form of a chemical bath.
    [473] It has also been found that the active compounds according to the invention exhibit potent insecticidal action against insects which destroy industrial materials.
    [474] The following insects may be mentioned as preferred examples, but are not limited to these:
    [475] Beetles , for example Hylotrupes bajulus , Chlorophorus pilosis , Anobium punctatum , Xestobium rufovillosum , Ptilinus pecticornis , Dendrobium pertinex , Ernobius mollis , Priobium carpini , Lyctus brunneus , Rick Lyctus africanus , Lyctus planicollis , Lyctus linearis , Lyctus pubescens , Trogoxylon aequale , Mintes lugi Minthes rugicollis , Xyleborus spp ., Tryptodendron spp ., Apate monachus , Bostrychus capucins , Heterobostrychus brunnes , Synoxylon spp ., Dinoderusminutus .
    [476] Hymenopterons , for example, Sirex jubencus , Urocerus gigas , Urocerus gigas taignus , Urocerus augur .
    [477] Termites , for example, Kalotermes flavicollis , Cryptotermes brevis , Heterotermes indicola , Reticulitermes flavipes , Reticulitermes santonensis , Reticulitermes lucifugus , Mastotermes darwiniensis , Zootermopsis nevadensis , Coff Cottertotermes formosanus .
    [478] Bristletails , for example Lepisma saccharina
    [479] Industrial materials in the context of the present invention are understood in the sense of non-living materials, preferably plastics, adhesives, glues, paper, cardboard, leather, wood, processed wood products, and coating compositions.
    [480] Materials to be protected from insect invasion are particularly preferably wood and processed wood products.
    [481] Wood and processed wood products which can be protected by the preparations according to the invention or mixtures comprising them are for example construction timber, wooden beams, railway sleepers, bridge components, breakwaters, vehicles made of wood. It is understood to mean wood products which are very commonly used in boxes, pallets, containers, telephone poles, wooden signs, windows and doors made of wood, plywood, chipboard, joining, or furniture for house construction or construction.
    [482] The active compounds can be used on their own in the form of concentrates or generally customary preparations, for example powders, granules, solutions, suspensions, emulsions or pastes.
    [483] The formulations mentioned are known per se, for example, by the active compound being at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, waterproofing agent, optionally drying agent and UV stabilizer and, And dyes and pigments and other processing aids.
    [484] The pesticidal compositions or concentrates used to preserve wood and woodworking products contain the active compounds according to the invention in concentrations of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
    [485] The amount of composition or concentrate that is used depends on the insect's habit and development and medium. The optimum amount of use can be determined by a series of tests in each case of use. In general, however, it is sufficient to use from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, based on the material to be preserved.
    [486] The solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or low volatility oily or oily organic chemical solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water, and emulsifiers and / or if appropriate Or humectant.
    [487] Organic chemical solvents which are preferably used are oily or oily solvents having an evaporation number of at least 35 and a flash point of at least 30 ° C, preferably at least 45 ° C. Substances used as oily and oily solvents that are low volatility and water-insoluble are suitable mineral oils or their aromatic fractions, or solvent mixtures containing mineral oils, preferably white spirit, petroleum and / or alkylbenzenes.
    [488] Mineral oil having a boiling range of 170 to 220 ° C, white oil having a boiling range of 170 to 220 ° C, spindle oil having a boiling range of 250 to 350 ° C, petroleum and aromatics having a boiling range of 160 to 280 ° C Compounds, terpentine oils and the like are advantageously used.
    [489] In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably Α-monochloronaphthalene is used.
    [490] Low volatility organic oily or oily solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., wherein the solvent mixture also has a flash point of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. If the pesticide / fungicide mixture can be dissolved or emulsified in the solvent mixture, it can be partially replaced by an intermediate or high volatility organic chemical solvent.
    [491] According to a preferred embodiment, a portion of the organic chemical solvent or solvent mixture is replaced with an aliphatic polar organic chemical solvent or solvent mixture. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as glycol ethers, esters and the like are preferably used.
    [492] The organic chemical binders used for the purposes of the present invention are known per se and can be diluted with water and / or dissolved, dispersed or emulsified in the organic chemical solvent used, and in combination dry oils, in particular acrylics. Rate resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene-couma A binder consisting of or comprising a physical dry binder based on cumarone resins, silicone resins, dry vegetable oils and / or dry oils and / or natural and / or synthetic resins.
    [493] Synthetic resins used as binders can be used in the form of emulsions, dispersions or solutions. Bitumen or bituminous materials can also be used as binders in amounts of up to 10% by weight. In addition, dyes, pigments, repellents, odour correctants and inhibitors or corrosion inhibitors known per se can be used.
    [494] According to the invention, it is preferred that the composition or concentrate contains at least one alkyd resin or modified alkyd resin and / or one dry vegetable oil as organic chemical binder. Alkyd resins having an oil content of at least 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
    [495] All or part of the above mentioned binders may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are used to prevent evaporation and also crystallization or precipitation of the active compounds. They preferably replace 0.01 to 30% of the binder (based on 100% binder used).
    [496] Plasticizers include phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, Stearates, for example butyl stearate or amyl stearate, oleate, for example butyl oleate, glycerol ether or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid esters do.
    [497] The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone or ethylenebenzophenone.
    [498] Possible solvents or diluents are, in particular, optionally water, as a mixture with one or more of the abovementioned organic chemical solvents or diluents, emulsifiers and dispersants.
    [499] Wood is particularly effectively preserved by large industrial scale injection methods, for example vacuum, double vacuum or compression treatment.
    [500] Ready-to-use compositions may also optionally contain other pesticides, and optionally also one or more fungicides.
    [501] Possible further mixing partners are preferably the insecticides and fungicides mentioned in WO 94/29 268. Compounds mentioned in this document are obvious components of the present application.
    [502] Particularly preferred mixing partners include insecticides such as chlorpyriphos, bombard, silafluorine, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron , Hexaflumuron, transflutrin, thiacloprid, methoxyphenozide, triflumuron, coulothianidine, spinosad and tefluthrin, and also fungicides such as epoxyconazole, hexacona Sol, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalyl, dichlorfluanid, tolylufluoride, 3-iodo-2-propynylbutyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one can be mentioned.
    [503] The compounds according to the invention can be used to protect objects contaminated with brine or seawater at the same time, for example from ship hulls, screens, nets, structures, marinas and signal transmission systems from contamination.
    [504] Species of fixed Oligochaetae , for example Serpulidae , and crustaceans and Ledamorpha family ( goose barnacle ), for example various Lepas and Contamination by the Scalpellum species, or species of the Balanomorpha family (acorn clam), for example Balanus or Pollicipes species, increases the frictional resistance of the vessel As a result, the energy consumption is high and the operating costs are significantly increased by frequently anchoring to dry docks.
    [505] Algae, e.g. ekto carboxylic crispus species (Ectocarpus sp.) And sera hatred species in addition to contamination by (Ceramium sp.), Mangak subclass (Cirripedia) the generic name (series fed crew star years old child (cirriped crustacea)) fixative section gapryu belonging to Contamination by the Entomostraca group is particularly important.
    [506] Surprisingly, the active compounds according to the invention have been found to have excellent antifouling action, alone or in combination with other active compounds.
    [507] By using the active compounds according to the invention alone or in combination with other active compounds, for example, bis (trialkyltin) sulfide, tri-n-butyltin laurate, tri-n-butyltin chloride, copper oxide ( I), triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymerized butyl titanate, phenyl- (bispyridine) bismuth chloride , Tri-n-butyltin fluoride, manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salt and copper salt of 2-pyridinethiol 1-oxide, bisdimethyldithiocarba Zinc zinc ethylenebisthiocarbamate, zinc oxide, copper (I) ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halide It is possible not to use heavy metals in or to significantly reduce the concentration of these compounds.
    [508] If desired, the ready-to-use antifouling paint may further comprise other active compounds, preferably fungicides, fungicides, herbicides, arachnids or other antifouling active compounds.
    [509] Preferred suitable components for combination with the antifouling composition according to the invention are as follows:
    [510] Algalicides, for example 2-t-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophene, diuron, endortal, pentine acetate, isoproturon, meta Benzthiazurone, oxyfluorfen, quinoclammine and terbutryn;
    [511] Fungicides, for example benzo [b] thiophenecarboxylic acid cyclohexylamide S, S-dioxide, diclofloanide, fluoropolpet, 3-iodo-2-propynyl butylcarbamate, tolylufluoride and azoles For example azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole;
    [512] Acaricides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb, trimetacarb and Fe-chelate; or
    [513] Conventional antifouling active compounds such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridinetriphenylborane, tetrabutyldistanoxane, 2,3,5,6-tetrachloro-4- (methyl Sulfonyl) -pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.
    [514] The antifouling composition used contains the active compound according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
    [515] In addition, antifouling compositions according to the invention are described, for example, in Ungerer, Chem. Ind . 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
    [516] Antifouling paints contain, in particular, binders, in addition to algae, fungicides, fungicide active compounds and pesticidal active compounds according to the invention.
    [517] Examples of approved binders include polyvinyl chloride in solvent systems, chlorinated rubbers in solvent systems, vinyl chloride / vinyl acetate copolymer systems in the form of acrylic resins, aqueous dispersions or organic solvent systems, particularly in aqueous systems, butadiene / Styrene / acrylonitrile rubbers, dry oils such as linseed oil, asphalt and epoxy compounds, modified cured resins or resin esters in combination with tar or bitumen, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.
    [518] If desired, the paint also contains inorganic pigments, organic pigments or colorants which are preferably insoluble in saline. The paint may also include a material such as colophonium so that the active compound is released slowly. The paint may also include plasticizers, modifiers that affect flowability, and other conventional ingredients. The compounds according to the invention or the abovementioned mixtures may also be incorporated into the auto-gloss antifouling system.
    [519] The active compounds are also suitable for controlling animal pests, especially insects, arachnids and mites, which appear in confined spaces such as houses, factory halls, offices, vehicle cabins and the like. They may be used alone or in combination with other active compounds and auxiliaries in household pesticidal products for controlling such pests. They are active against sensitive and resistant species and all stages of development. These pests include:
    [520] Scorpion (Scorpionidea) tree, for example tooth portion oxide Kita Taunus (Buthus occitanus).
    [521] From the order of Acarina , for example Argas persicus , Argas reflexus , Bryobia spp ., Dermanyssus gallinae , Glycipagus Glyciphagus domestigus , Ornithodorus moubat , Rhipicephalus sanguineus , Trombicula alfreddugesi , Neutrombulara autumalia autumn ), Dermatophagoides pteronissimus , Dermatophagoides forinae .
    [522] Araneae , for example Aviculariidae , Araneidae
    [523] Opiliones , for example Pseudoscorpiones chelifer , Pseudoscorpiones cheiridium , Opiliones phalangium .
    [524] Isopoda , for example Oniscus asellus , Porcellio scaber .
    [525] Millipedes (Diplopoda) tree, for example Blast niul loose obtain Tula tooth (Blaniulus guttulatus), poly des mousse species (Polydesmus spp.).
    [526] The genus Chilopoda , for example Geophilus spp .
    [527] Zygentoma , for example Ctenolepisma spp. , Lepisma saccharina , Lepismodes inquilinus .
    [528] Neck of Blattaria , for example Blatta orientalis , Blattella germanica , Blattella asahinai , Leucophaea maderae , Panclo Panchlora spp. , Parcoblatta spp ., Periplaneta australasiae , Periplaneta americana , Periplaneta brunnea , Periplaneta brunnea Periplaneta fuliginosa , Supella longipalpa .
    [529] From the genus Saltatoria , for example Acheta domesticus .
    [530] Dermaptera , for example Forficula auricularia .
    [531] Termites ( Isoptera ), for example Kalotermes spp. , Reticulitermes spp .
    [532] Psocoptera species, for example Lepinatus spp. , Liposcelis spp .
    [533] Beetles (Coleoptera) Thursday, for example, in the eyes Trail Taunus species (Anthrenus spp.), Oh ridden pandanus species (Attagenus spp.), No scalpel test species (Dermestes spp.), Latte, tea Couscous Duck Party (Latheticus oryzae) , Necrobia spp. , Ptinus spp ., Rhizopertha dominica , Sitophilus granarius , Sitophilus oryzae , Sito Sitophilus zeamais , Stegobium paniceum .
    [534] Diptera , for example Aedes aegypti , Aedes albopictus , Aedes taeniorhynchus , Anopheles spp . , Calliphora erythrocephala , Chrysozona pluvialis , Culex quinquefasciatus , Culex pipiens , Culex pipiens , Culex tarsalis tarsalis , Drosophila spp. , Fannia canicularis , Musca domestica , Phlebotomus spp. , Sarcophaga canaria carnaria ), Simulium spp ., Stomoxys calcitrans , Tipula paludosa .
    [535] Lepidoptera , for example Achroia grisella , Galleria mellonella , Plodia interpunctella , Tinea cloacella , Tinnea pelionel Tinea pellionella , Tineola bisselliella .
    [536] Siphonaptera tree, for example Ctenocephalides canis , Ctenocephalides felis , Pulex irritans , Tunga penetrans , Xenopsila Xenopsylla cheopis .
    [537] Bee (Hymenopera) tree, for example camphorsulfonic no tooth Herr cool LEA Taunus (Camponotus herculeanus), La siwooseu loosened furnace Versus (Lasius fuliginosus), La siwooseu nigeo (Lasiusniger), La siwooseu Umbra tooth (Lasius umbratus), mono mode Monomorium pharaonis , Paravespula spp. , Tetramorium caespitum .
    [538] Anoplura , for example Pediculus humanus capitis , Pediculus humanus corporis , Pthirus pubis .
    [539] From the order of Heteroptera , for example Cimex hemipterus , Cimex lectularius , Rhodnius prolixus , Triatoma infestans .
    [540] In the field of household pesticides, they are used alone or in combination with other suitable active compounds, for example phosphate esters, carbamates, pyrethroids, neonicotinoids, growth regulators or other known pesticide groups.
    [541] They are aerosols, pressureless spray products, for example pumps and atomizer sprays, automatic spray systems, sprayers, foams, gels, cellulose or polymer evaporation tablets, liquid evaporators, gels and membrane evaporators As evaporation products, propellant-operated evaporators, energy-free or passive evaporators, moth paper, moss bags and moss gels, used as granules or powders in sparing bait or manned places.
    [542] The active compounds according to the invention can also be used as defoliants, desiccants, haulmkillers and in particular weed killer. Weeds, in the broadest sense, mean all plants that grow in unwanted places. Whether the substance according to the invention acts as a total or selective herbicide depends essentially on the amount used.
    [543] The active compounds according to the invention can be used, for example, in connection with the following plants:
    [544] To in the dicotyledonous weed Abu epothilone (Abutilon), probably Lantus (Amaranthus), Ambrosia (Ambrosia), Arnaud is (Anoda), Ante Miss (Anthemis), sick ness (Apanes), art Reflex (Atriplex), belriseu (Belis) , a non-dense (Bidens), capsule La (Capsella), carboxylic Douce (Carduus), cassia (Cassia), center urea (Centaurea), Ke-established rhodium (Chenopodium), unsealing syum (Cirsium), convolution bulruseu (Convolvulus), the Natura (Datura), des modyum (Desmodium), the Mex (Emex), Erie during drought (Erysimum), yuporeubiah (Euphorbia), Gale option system (Galeopsis), ground Soga (Galinsoga), gallium (Galium), Hi-bis Hibiscus , Ipomoea , Kochia , Lamium , Lepidium , Lindernia , Matricaria , Mentha , Mer Alice Kurihara (Mercurialis), and Mulu (Mullugo), Mio bovine teeth (Myosotis), Papa Bell (Papaver), Parque non-Tees (Pharbitis), flan And (Plantago), Polygonum (Polygonum), Fort Tula car (Portulaca), La nunkul Ruth (Ranunculus), Rafa Augustine (Raphanus), roripa (Rorippa), as Tala (Rotala), Lou Mex (Rumex), buy Solar ( Salsola ), Senecio , Sesbania , Sida , Sinapis , Solanum , Sonchus , Sphenoclea , Stellaria ), fall sakum (Taraxacum), teulra RY (Thlaspi), Tripoli Titanium (Trifolium), Ur urticae (Urtica), Veronica (Veronica), viola (viola) and greater santyum (Xanthium).
    [545] To the genus dicotyledonous crops: arachis (Arachis), beta (Beta), Brassica (Brassica), Cucumis (Cucumis), Cuckoo Le Vita (Cucurbita), tooth not patronize (Helianthus), Dow Syracuse (Daucus), Glee Cinemax (Glycine), announced europium (Gossypium), Ipoh Moe Oh (Ipomoea), Rock Dukas (Lactuca), rinum (Linum), Rico Percy cone (Lycopersicon), Nico tiahna (Nicotiana), Pace come loose (Phaseolus), pisum ( Pisum ), Solanum and Vicia ,
    [546] Monocotyledonous weeds in the To: Oh the way ropseu (Aegilops), Agrobacterium Piron (Agropyron), Agrobacterium seutiseu (Agrostis), Alor page kuruseu (Alopecurus), ahpera (Apera), ABE or (Avena), beuraki Aria (Brachiaria), Bro Moose (Bromus), Sen Cruz (Cenchrus), nose Melina (Commelina), Sino money (Cynodon), between Peru's (Cyperus), daktil lock'll help (Dactyloctenium), D. other Ria (Digitaria), Echinacea-no claws ah ( Echinochloa , Eleocharis , Eleusin , Eragrotis , Eriochloa , Festuca , Fimbristylis , Heteranthera , impeller other (Imperata), drought (Ischaemum), repto claw O (Leptochloa), rolryum (Lolium), mono Korea (Monochoria), Trapani glutamicum (Panicum), Paz palrum (Paspalum), Palladium-less (Phalaris) to yiseuka, Phleum , Poa , Rottboellia , Sagittar ia ), Scirpus , Setaria and Sorghum .
    [547] To the genus monocotyledonous crops: Allium (Allium), Ananas (Ananas), aspartate Goose (Asparagus), ABE or (Avena), Johor deum (Hordeum), duck party (Oryza), Trapani Qom (Panicum), Saccharomyces Room (Saccharum ), three-Calais (Secale), sorbitol gum (Sorghum), Tea tree Calais (Triticale), the tree tikum (Triticum) and Jea (Zea).
    [548] However, the use of the active compounds according to the invention is not limited at all in the above, but also extends to other plants in the same way.
    [549] The active compounds according to the invention are suitable for the overall control of weeds, depending on their concentration, for example on industrial zones and railway tracks, and on walkways and plazas, with or without trees. Likewise, the active compounds according to the invention are for example plantations, ornamental water plantations, orchards, vineyards, citrus fields, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, palm plantations, cocoa plantations, soft fruit plantations. And weeds in perennial crops of hop fields, grass, turf and pasture, and selectively for weeds in annual crops.
    [550] The compounds of the general formula (I) according to the present invention show a strong herbicidal activity and a broad spectrum of activity when used on the ground of soil and plants. They are also suitable to some extent selectively control monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops by both pre- and post-germination methods.
    [551] The compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases at certain concentrations or application rates. If desired, they can also be used as intermediates or precursors for synthesizing other active compounds.
    [552] Active compounds include solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials in which the active compound has been injected, and microcapsules in polymeric materials. It can be converted to a conventional formulation.
    [553] These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers.
    [554] If the extender used is water, it is also possible to use organic solvents, for example as auxiliary solvents. Primarily suitable liquid solvents include aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils. Strong aliphatic hydrocarbons such as aliphatic hydrocarbons, butanol or glycols and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide and water.
    [555] Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as solid silica, alumina and silicates. Suitable granular carriers for granules are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, or synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut shells, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , Arylsulfonates or protein hydrolysates. Suitable dispersants are for example lignosulphite waste liquors and methylcellulose.
    [556] Tackifiers such as carboxymethylcellulose, and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used for Other possible additives are mineral oils and vegetable oils.
    [557] Traces such as colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants and traces such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can also use nutrients.
    [558] The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.
    [559] When controlling weeds, the active compounds according to the invention can be used on their own or in mixtures with substances known to improve compatibility with herbicides and / or crops (“detoxifying agents”), Finished product formulations or tank mixes are possible. It is also possible to admix with a weed killer comprising one or more known herbicides and safeners.
    [560] Possible components in the mixture are known herbicides such as acetochlor, acifluorfen (-sodium), acloniphene, alachlor, alkoxydim (-sodium), amethrin, amikabazone, amidochlor, amido Dosulfuron, anilophos, asulam, atrazine, azaphenidine, azimsulfuron, beflutamide, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), betazone, benzfendizone, Benzobicyclone, benzophenab, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromophenoxime, bromoxynil, butachlor, butafenacyl ( Allyl), butoxydim, butyrate, carfenstrol, caroxydim, carbetamid, carpentrazone (-ethyl), clomethoxyphene, chlorambene, chloridazone, chlorimuron (-ethyl) , Chlornitropen, chlorsulfuron, chlortoluron, cinidon (-ethyl), citmethyline, cynosulfuron, clepoxydim, cletodim, chlor Dinapov (-propargyl), clomazone, clomeprop, clopyralide, clopyrasulfuron (-methyl), cloransullam (-methyl), cumyluron, cyanazine, cybutrin, cycloate , Cyclosulfamuron, cyacryldim, sihalofop (-butyl), 2,4-D, 2,4-DB, desmedimaph, dialate, dicamba, dicloprop (-P), Diclofo (-methyl), Diclosulam, Dietatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethamethrin, Dimetholin Metheneamide, dimexiflom, dinitramine, diphenamide, diquat, dithiopyr, diuron, dimron, eprofodan, EPTC, esprocarb, etafluralin, etamethsulfuron (-methyl), eto Fumesate, ethoxyphene, ethoxysulfuron, etobenzanide, phenoxaprop (-P-ethyl), pentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), plazasulfu , Florasullam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flumetsulam, Flumichlorac (-pentyl), Flumioxazine, Flumipro Fin, flumetsulam, fluoromethuron, fluorochloridone, fluoroglycopene (-ethyl), flupoxam, flupropacyl, flupyrsulfuron (-methyl, -sodium), flurenol (-butyl) , Flulidone, fluoroxypyr (-butoxypropyl, -octyl), fluprimidol, flutamone, fluthiacet (-methyl), flutiamide, pomessafen, foramsulfuron, glufosinate ( -Ammonium), glyphosate (-isopropylammonium), halosafen, halooxyphosph (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl), imazamethapyr, forehead Mazox, imazapic, imazapyr, imazaquin, imazetapyr, imazasulfuron, iodosulfuron (-methyl, -sodium), isoxynyl, isoprophalin, isoproturon, Souron, isoxaben, isoxaclortol, isoxaplutol, isoxapyrupif, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitrone, metaza Chlor, metabenzthiazuron, methopenzuron, methopromurone, (alpha-) metolachlor, methotsalam, methoxuron, metribuzin, metsulfuron (-methyl), mololinate, monolinuron, Naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzaline, oxadiargyl, oxadione, oxasulfuron, oxazilomepon, oxyfluorfen, para Couart, pellagonic acid, pendimethalin, pendralline, pentoxazone, penmedipalm, picolinafen, piperophosph, pretilachlor, primisulfuron (-methyl), profluzol, promethrin, pro Pachlor, propanyl, propaquizapov, propisochlor, propoxycarbazone (-sodium), propizamide, propulfo Bro, Prosulfuron, Piraflufen (-ethyl), Pirazogil, Pyrazolate, Pirazosulfuron (-ethyl), Pyrazoxifen, Pyribenzoxime, Pyributycarb, Pyridate, Pyriditol, Pyrup Thalilide, pyriminobac-(-methyl), pyrithiobac (-sodium), quinclolac, quinmerac, quinoclamine, quizaropof (-P-ethyl, -P-tefuryl), rimsulfuron, Cetoxydim, simazine, cymetrine, sulforion, sulfentrazone, sulfomethuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebutiuuron, tetraproxydim, terbutylazine, Terbutrin, tenylchlor, thiafluamide, thiazopyr, thiadiazimine, thifensulfuron (-methyl), thiobencarb, thiocarbazil, tralcoxysid, trialate, triasulfuron, tribenuron (-Methyl), triclopyr, tridiphane, trituraline, trilockulfurfuron, triflusulfuron (-methyl) and tritosulfuron.
    [561] Known safeners, for example AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cymetrinyl, 2,4-D, DKA-24, dichlormide, dimrone, fenkle Rorim, fenchlorazole (-ethyl), flurazole, fluxofimem, furylazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG -191, oxavetrinyl, PPG-1292, R-29148 are also suitable for the mixture.
    [562] Mixtures with other known active compounds are also possible, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil remediators.
    [563] The active compounds can be used on their own, in the form of their preparations or in the form of further dilution thereof, for example in ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in conventional manner, for example by watering, spraying, atomizing or broadcasting.
    [564] The active compounds according to the invention can be applied both before or after germination of plants. They can also be incorporated into the soil before sowing.
    [565] The amount of active compound used can vary within a relatively wide range. This is essentially dependent on the nature of the desired effect. Generally, the amount used is 1 g to 10 kg, preferably 5 g to 5 kg of active compound per hectare of soil surface.
    [566] The materials according to the invention exhibit strong microbicidal activity and can be used to control unwanted microorganisms, for example fungi and bacteria, in crop protection and material protection.
    [567] Fungicides include Plasmodiophoromycetes , Oomycetes , Chytridiomycetes , Zygomycetes and Ascomycetes in crop protection. , Basidiomycetes and Deuteromycetes can be used to rescue.
    [568] Fungicides may be used to remedy the pseudo mono Ada years old child (Pseudomonoadaceae), Li Jovi Asia (Rhizobiaceae), Enterobacter bacteria years old child (Enterobacteriaceae), Corey four bacteria years old child (Corynebacteriaceae) and Streptomyces setae years old child (Streptomycetaceae) in crop protection .
    [569] Some examples of pathogens that cause fungal and bacterial diseases of the genus above are mentioned below, but not limited to:
    [570] Xanthomonas species, for example Xanthomonas campestris fib . Orissa ( Xanthomonas campestris pv. Oryzae );
    [571] Pseudomonas (Pseudomonas) species, such as blood V Pseudomonas when Manly. Lacrymans ( Pseudomonas syringae pv. Lachrymans );
    [572] Erwinia species, for example Erwinia amylovora ;
    [573] Pythium species, for example Pythium ultimum ;
    [574] Phytophthora species, for example Phytophthora infestans ;
    [575] Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis ;
    [576] Plasmopara species, for example Plasmopara viticola ;
    [577] Bremia species, for example Bremia lactucae
    [578] Peronospora species, for example Peronospora pisi or Peronospora brassicae ;
    [579] Erysiphe species, for example Erysiphe graminis ;
    [580] Sphaerotheca species, for example Sphaerotheca fuliginea ;
    [581] Podosphaera species, for example Podosphaera leucotricha ;
    [582] Venturia species, for example Venturia inaequalis ;
    [583] Pyrenophora species, for example Pyrenophora teres or Pyrenophora graminea (conidia form: Drechslera ), isoform: Helmintosporium ( Helminthosporium ));
    [584] Cochliobolus species, for example Cochliobolus sativus (conidia form: Dresslera, isoform: Helmintosporium);
    [585] Uromyces species, for example Uromyces appendiculatus ;
    [586] Puccinia species, for example Puccinia recondita ;
    [587] Sclerotinia species, for example Sclerotinia sclerotiorum ;
    [588] Tilletia species, for example Tilletia caries ;
    [589] Ustilago species, for example Ustilago nuda or Ustilago avenae ;
    [590] Pellicularia species, for example Pellicularia sasakii ;
    [591] Pyricularia species, for example Pyricularia oryzae ;
    [592] Fusarium (Fusarium) species, such as Fusarium cool morum (Fusarium culmorum);
    [593] Botrytis species, for example Botrytis cinerea ;
    [594] Septoria species, for example Septoria nodorum ;
    [595] Leptosphaeria species, for example Leptosphaeria nodorum ;
    [596] Cercospora species, for example Cercospora canescens ;
    [597] Alternaria species, for example Alternaria brassica and
    [598] Pseudocercosporella species, for example Pseudocercosporella herpotrichoides .
    [599] The active compounds according to the invention also show very good strengthening action in plants. Thus, they can be used to confer plant protection against invasion by unwanted microorganisms.
    [600] As used herein, plant fortifying (resistance-inducing) substances should be understood to mean substances that can stimulate the plant's defense system so that when plants are inoculated with undesired microorganisms, the plant is significantly resistant to these microorganisms. do.
    [601] In this case, unwanted microorganisms should be understood to mean phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be used to protect plants from infection by the aforementioned pathogens for a certain period of time after treatment. The period of protection is generally 1 to 10 days, preferably 1 to 7 days, after treatment of the plants with the active compounds.
    [602] Treatment of the plant's tops, breeding stems and seeds, and soils is possible in that the plants are tolerant to the active compounds at the concentrations necessary to control plant diseases.
    [603] The active compounds according to the invention can also be used to increase crop yields. In addition, they are low toxicity and exhibit excellent plant compatibility.
    [604] The active compounds according to the invention can also be used as herbicides to influence plant growth or to control animal pests at certain concentrations and application rates. If desired, they can also be used as intermediates and precursors for synthesizing other active compounds.
    [605] The compounds according to the invention can be used to protect industrial materials from invasion and destruction by unwanted microorganisms.
    [606] Industrial materials herein are to be understood as meaning non-living materials prepared for industrial use. For example, industrial materials which are intended to be protected by the active compounds according to the invention from changes or destruction by microorganisms can be applied to adhesives, glues, paper, cardboard, textiles, leather, wood, paints, plastic products, cooling lubricants and microorganisms. It may be other material that can be infected or destroyed by. Within the scope of the material to be protected, mention may also be made of parts of the production plant, for example cooling water circuits, which may be adversely affected by the growth of microorganisms. Industrial materials that may be mentioned within the scope of the present invention are preferably adhesives, glues, paper, cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
    [607] Microorganisms capable of decomposing or changing industrial materials can be mentioned, for example, bacteria, fungi, yeast, algae and slime organisms. The active compounds according to the invention preferably act on fungi, in particular filamentous fungi, wood discoloration and wood destruction fungi (bacsidomycetes) and on modified organisms and algae.
    [608] Microorganisms of the following genus may be mentioned by way of example:
    [609] Alternaria , for example Alternaria tenuis
    [610] Aspergillus , for example Aspergillus niger
    [611] Kaeto hate (Chaetomium), for example kaeto hatred Globo breath (Chaetomium globosum),
    [612] Coniophora , for example Coniophora puetana ,
    [613] Lentinus , for example Lentinus tigrinus ,
    [614] Penicillium , for example Penicillium glaucum ,
    [615] Polyporus , for example Polyporus versicolor ,
    [616] Aureobasidium , for example Aureobasidium pullulans ,
    [617] 'S nucleoside poma (Sclerophoma), for example, scan nucleoside poma pita EO pillar (Sclerophoma pityophila),
    [618] Trichoderma (Trichoderma), for example, to irregularities in Trichoderma (Trichoderma viride),
    [619] Escherichia , for example Escherichia coli ,
    [620] Pseudomonas (Pseudomonas), for example Pseudomonas rugi ah industrial (Pseudomonas aeruginosa) and
    [621] Staphylococcus , for example Staphylococcus aureus .
    [622] The active compounds, depending on their particular physical and / or chemical properties, are conventional formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules in polymeric and seed coating compositions. And ULV coolants and warmers.
    [623] These formulations are known methods, for example by mixing the active compounds with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers. It is manufactured by. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Primarily, suitable liquid solvents include aromatic compounds such as xylene, toluene or alkylnaphthalene; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide and dimethylsulfoxide, or water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at standard temperatures and atmospheric pressures, for example halogenated hydrocarbons and also aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable granular carriers for granules are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, or synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husks, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , Arylsulfonates or protein hydrolysates. Suitable dispersants are for example lignosulphite waste liquors and methylcellulose.
    [624] Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural and synthetic phospholipids such as cephalin and lecithin Can be. Other possible additives are mineral oils and vegetable oils.
    [625] Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic pigments such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; The same micronutrients may be used.
    [626] The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.
    [627] The active compounds according to the invention can also be used on their own or as a mixture with known fungicides, fungicides, acaricides, nematicides or insecticides, for example in order to prevent broadening the activity spectrum or developing resistance in the formulation thereof. May exist. In many cases a synergistic effect is obtained, ie the activity of the mixture is greater than that of the individual components.
    [628] Examples of suitable mixing components are as follows:
    [629] Fungicides:
    [630] 2-phenylphenol, 8-hydroxyquinoline sulfate, acibenzola-S-methyl, aldimorph, amidoflumet, ampropyl force, ampropyl force-potassium, andoprim, anilazin, azaconazole, subfamily Cystrovin, Benalactyl, Benodanil, Benomyl, Ventiavalicab-isopropyl, Benzamacryl, Benzamacryl-Isobutyl, Villanaphos, Vinapacryl, Biphenyl, Vitertanol, Blastisidin-S , Bromuconazole, burimate, butiobate, butylamine, calcium polysulfide, capsaicin, captapol, captan, carbendazim, carboxycin, capropamide, carbon, quinomethionate, clobenthiazone , Chlorphenazole, chloroneb, chlorothalonil, clozolinate, clozilacon, cyazopamide, cyflufenamide, cymoxanyl, cyproconazole, cyprodinyl, cyprofuram, Dagger G, Debacar, diclofloanid, diclone, dichlorophene, diclosa Met, Diclomezine, Dichloran, Dietofencarb, Diphenoconazole, Diflumethorim, Dimethyrimol, Dimethomorph, Dimoxistrobin, Diconazole, Diniconazol-M, Dinocap, Di Phenylamine, Dipyrithione, Ditalimfoss, Dithianon, Dodine, Dragoxolone, Edifene Force, Epoxyconazole, Ethaboxam, Ethyrimol, Etridazole, Pamoxadon, Phenamidone, Penapanyl, Phenari Mole, fenbuconazole, fenfuram, phenhexamide, phenytropane, phenoxanyl, fenpiclonil, phenpropidine, fenpropormoff, ferbam, fluazinam, flubenzimin, fludioxonil , Flumetober, flumorph, fluoromid, fluoxastrobin, fluquinconazole, fluprimidol, flusilazole, flusulfamid, flutolanyl, flutriafol, follet, pocetyl-Al, Pocetyl-sodium, fuberidazole, furalacyl, furametpyr, purcarbanyl, purmecyclolox, guaztine, hexachlorobenzene, Saconazole, hymexazole, imazaryl, imibenconazole, iminottadine triacetate, iminottadine tris (albesil), iodocarb, ifconazole, ifprobenfos, ifprodione, isovalicacarb, irumamycin , Isoprothiolane, isovaledione, kasugamycin, cresoxime-methyl, mancozeb, maneb, meperimzone, mepanipyrim, mepronil, metallaxyl, metallaxyl-M, metconazole, metasulfoca Bromo, metfuroxam, metiram, metominostrovin, metsulfobox, midiomycin, michaelrobutanyl, michaelrozoline, natamycin, nicobifen, nitrotal-isopropyl, nobiflumuron, noarimol , Opuras, orissastrobin, oxadixyl, oxolinic acid, oxofonabol, oxycarboxine, oxypentin, paclobutrazole, pepurazoate, fenconazole, pencicuron, phosphodiphene, phthalide, peacock Cystrovin, Pipeline, Polyoxin, Polyoxolin, Pro Benzazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, proquinazide, prothioconazole, pyraclostrobin, pyrazophos, pyripe Knox, pyrimethanyl, pyroquilon, pyrroxyfur, pyrrolenitrine, quinconazole, quinoxifen, quintogen, simeconazole, spiroxamine, sulfur, tebuconazole, teclophthalam, technazen, tet Cyclosis, Tetraconazole, Tiabendazole, Thiathiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl, Tolylufluoride, Triadimefon, Triadime Menol, Triazbutyl, Triazoxide, Tricyclamide, Tricyclazole, Tridemorph, Trixystrobin, Tripleluminazole, Triporin, Triticazole, Uniconazole, Validamycin A, Vinclo Sleepy, geneb, zilam, oxamid, (2S) -N- [2- [4-[[3- (4-chlorophenyl) -2-pro Finyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsulfonyl) amino] butanamide, 1- (1-naphthalenyl) -1H-pyrrole-2,5-dione , 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3 -Dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3,4,5-trichloro-2,6-pyridinedicarbonitrile, actinobate, Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol, methyl 1- (2,3-dihydro-2,2-dimethyl- 1H-inden-1-yl) -1H-imidazole-5-carboxylate, potassium monocarbonate, N- (6-methoxy-3-pyridinyl) cyclopropanecarboxamide, N-butyl-8- (1 , 11-dimethylethyl) -1-oxaspiro [4.5] decane-3-amine, sodium tetrathiocarbonate and copper salts and preparations, for example Bordeaux mixtures, copper hydroxide, copper naphthenate, copper oxychloride Copper Sulfate, Cupraneb, Copper Oxide, Mancopper, Auxin-copper.
    [631] disinfectant:
    [632] Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.
    [633] Pesticides / Acaricides / Nematicides:
    [634] Abamectin, ABG-9008, Acetate, Acequinosyl, Acetamiprid, Acetoprole, Acrinatrin, AKD-1022, AKD-3059, AKD-3088, Alanicab, Aldicarb, Aldoxicarb, Allerthrin , Alletrin 1R-isomer, alpha-cypermethrin (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ 60541, azadirachtin, azamethicose, azinfos-methyl, azine Phosph-ethyl, azocyclotin,
    [635] Bacillus pophilia, Bacillus sp. Erytheus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, baculovirus Seth, Beauveria Bassiana, Beauveria Tenella, Bendiocarb, Benfuracab, Bensultap, Benzoxmate, Betacyfluthrin, Betacypermethrin, Bifenazate, Bifenthrin, Vinapacryl, Bio Alletrin, Bioaletrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl, bromopropylate, bromfenbinfos (-Methyl), BTG-504, BTG-505, bufencarb, buprofezin, butathiophos, butocarboxime, butoxycarboxime, butylpyridaben,
    [636] Kadusafos, campechlor, cabaril, cabofuran, cabofennotion, carbosulphan, katop, CGA-50439, quinomethionate, chlordan, chlordimeform, chloretocab, chlorethoxyphosph, chlorfenapyr , Chlorfenbin Force, Chlorfluazuron, Chlormephos, Chlorobenzylate, Chloropicrine, Chlorproxyfen, Chlorpyriphos-methyl, Chlorpyriphos (-ethyl), Clovafortrin, Chromafenozide, Cis-Sai Permethrin, cis-resmethrin, cis-permethrin, clocitrin, cloetocarb, clopentezin, clotianidine, clothiazobene, cordlemon, coomaphos, cyanophenfos, cyanophos, cycloprene, Cycloprotrin, cydiapomonella, cyfluthrin, sihalothrin, cyhexatin, cypermethrin, cyphenotrin (1R-trans-isomer), cyromargin,
    [637] DDT, deltamethrin, demethone-S-methyl, demethone-S-methylsulfone, diafenthiuron, dialilifos, diazinone, diclopention, dichlorbos, dicopol, dicrotophos, dicy Clanyl, diflubenzuron, dimethoate, dimethylvinforce, dinobutone, dinocap, dinotefuran, diophenolran, disulfotone, docusat-sodium, dofenapine, DOWCO-439,
    [638] Eflusilanate, emamectin, emamectin-benzoate, empentrin (1R-isomer), endosulfan, entomorphora species (spp.), EPN, espenvalelate, ethiophencarb, ethiprole, ethione , Etoprophos, etofenprox, ethoxazole, erythropose,
    [639] Pampur, Penamifoss, Penazaquine, Penbutatin Oxide, Penfluthrin, Phenythrothione, Phenobucarb, Phenothiocarb, Phenoxa Cream, Phenoxycarb, Penpropartlin, Penpyrad, Penpyri Trine, Phenpyroximate, Pensulfothion, Pention, Pentripanyl, Fenvalrate, Fipronil, Flornicamid, Fluacrypyrim, Fluazuron, Flubenzimin, Flubrositeinate, Flusai Clock-Suron, Flusiteinate, Flufenerim, Flufenoxuron, Flufenprox, Flumethrin, Flupyrazophos, Flutenzin (Flufenzin), Fluvalinate, Phonophos, Formate, Formimoti On, phosphmethyllan, phosphthiazate, fufenfenx (fluxyfen), furathiocarb,
    [640] Gamma-HCH, gosiflure, granlure, granulosis virus,
    [641] Halfenprox, halopenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexthiaxose, hydramide, hydroprene,
    [642] IKA-2002, imidacloprid, imiprotrin, indoxacarb, iodofenfos, iprobenfos, isosafos, isofenfos, isoprocarb, isoxation, ivermectin,
    [643] Japonilure,
    [644] Cardetrin, nuclea polyhedrosis virus, quinoprene,
    [645] Lambda-cyhalothrin, lindan, lufenuron,
    [646] Malathion, mecarbam, mesulfenfos, metaldehyde, metham-sodium, methacryfoss, metamidophos, metharium anisoplier, metharium flavoviride, methidadion, methiocarb, Metomil, Metoprene, Methokcyclo, Methoxyfenozide, Metholcarb, Metoxadiazone, Mevinforce, Milvemectin, Milbemycin, MKI-245, MON-45700, Monoclotophos, Moxidecine, MTI- 800,
    [647] NALRED, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768 , Novaluron, Nobiflumuron,
    [648] OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, ometoate, oxamyl, oxydemethone-methyl,
    [649] Paesilomyses pumosorusus, parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-trans isomer), pentoate, forrate , Posalon, phosphmet, phosphamidone, phosphocarb, bombarded, piperonyl butoxide, pyrimicab, pyrimifos-methyl, pyrimifos-ethyl, praletrin, propenophosphate, promecab , Propaphos, propargite, propeptamphos, propofur, prothiophos, protoate, protrifenbut, pymetrozine, pyraclophos, pyresmethrin, pyrethrum, pyridaben, pyridalyl, Pyridapentione, pyridathione, pyrimidipene, pyriproxyfen,
    [650] Quinal Force,
    [651] Resmethrin, RH-5849, ribavirin, RU-12457, RU-15525,
    [652] S-421, S-1833, Salityon, Cebu Force, SI-0009, Silafluorene, Spinosad, Spirodiclofen, Spiromethifene, Sulfluramid, Sulpotep, Sulprophos, SZI-121,
    [653] Tau-fluvalinate, tebufenozide, tebufenpyrad, tebupyrimifos, teflubenzuron, tefluthrin, temefos, themibinfos, terbam, terbufoss, tetrachlorbinfos, tetradipon, Tetramethrin, tetramethrin (1R-isomer), tetrasul, theta-cypermethrin, tiacloprid, thiamethoxam, thiapronyl, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thio Panox, Thiomethone, Thiosulfato-Sodium, Turingiencin, Tolfenpyrad, Tralositerin, Tralomethrin, Transfluthrin, Triarathene, Triamate, Triazophos, Triazonone, Triclofenidine , Trichlorphone, triple lumuron, trimetacarb,
    [654] Amidothione, vaniliprole, burbutin, vertisium lecanini,
    [655] WL-108477, WL-40027,
    [656] YI-5201, YI-5301, YI-5302,
    [657] XMC, xylylcarb,
    [658] ZA-3274, Zeta-Cypermethrin, Zolapropos, ZXI-8901,
    [659] Compound 3-methylphenyl propylcarbamate (chumaside Z),
    [660] Compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS-Reg.No 185982-80-3) and corresponding 3-endo-isomers (CAS-Reg.No. 185984-60-5) (WO-96 / 37494, WO-98 / 25923),
    [661] And insecticidal active plant extracts, nematicides, fungi or viruses.
    [662] Other known active compounds such as herbicides or mixtures with fertilizers and growth regulators are also possible.
    [663] In addition, the compounds of general formula (I) according to the invention have very good antibacterial activity. These particular skin fungi (dermatophyte) and yeasts, molds and more fungi (e.g. Candida albicans (Candida albicans), Candida glabrata (Candida species (Candida species), such as Candida glabrata)) and epi Dermo python flow kosum ( Epidermophyton floccosum), Aspergillus nigeo (Aspergillus noger) and Aspergillus Fu fumigatus (Aspergillus fumigatus) and tricot python species such as Aspergillus species (Aspergillus species), tricot Python menta him fight (Trichophyton mentagrophyte) (Trichophyton species , Microsporon canis and Microsporon species such as audouinii have a very broad spectrum of antimicrobial activity. These fungal lists do not limit the antimicrobial spectrum being covered at all and are for illustrative purposes only.
    [664] The active compounds can be used on their own, in the form of their preparations, or in the preparations prepared from them, such as ready-to-use solutions, suspensions, hydrating powders, pastes, soluble powders, powders and granules. This applies in conventional manner, for example by spraying, spraying, misting, spraying, spraying, foaming, spraying and the like. In addition, the active compounds may be applied by a microvolume method or the active compound preparation or the active compound itself may be injected into the soil. Seeds of plants are also treatable.
    [665] When the active compounds according to the invention are used as fungicides, the application rates can vary within wide ranges depending on the application form. When treating a part of the plant, the application rate of the active compound is generally 0.1 to 10,000 g / dL, preferably 10 to 1,000 g / dL. For seed dressings, the application rate of the active compound is generally from 0.001 to 50 g, preferably from 0.01 to 10 g per kg of seed. When treating the soil, the application rate of the active compound is generally 0.1 to 10,000 g / dL, preferably 1 to 5,000 g / dL.
    [666] Examples of preparation and use of the active compounds according to the invention are illustrated in the following examples.
    [667] Manufacturing Example:
    [668] Example I-1-1
    [669]
    [670] 0.24 mL of sulfuryl chloride and 1 mL of anhydrous chloroform were added dropwise to 0.98 g of the compound of Example (I-1-a-18) (WO 99/48869) in 30 mL of anhydrous chloroform at 0-5 ° C. After 30 minutes, the reaction was complete (monitored by thin layer chromatography).
    [671] The reaction mixture is washed with NaHCO 3 solution, the organic phase is dried and the solvent is distilled off.
    [672] Yield: 0.85 g (78% of theory), Melting Point 175 ° C.
    [673] Example I-1-29
    [674]
    [675] 0.33 g (5.2 mmol) of fuming nitric acid was added dropwise to 0.98 g of the compound of Example (I-1-a-18) (WO 99/48869) in 45 mL of anhydrous chloroform at room temperature. After 30 minutes, the reaction was complete (monitored by thin layer chromatography).
    [676] The reaction mixture was added to 40 ml of ice water, the organic phase was separated and the aqueous phase was extracted with dichloromethane, then the combined organic phases were dried. Then the solvent was distilled off. The residue was purified by silica gel chromatography (dichloromethane, ethyl acetate, 10: 1).
    [677] Yield: 0.75 g (67% of theory), Melting point 157 ° C.
    [678] Similar to Example (I-1-1) and according to the general preparation, compounds of the general formula (I-1) were obtained.
    [679] Table A
    [680]
    [681]
    [682]
    [683] Example I-2-1
    [684]
    [685] A solution of sulfuryl chloride (0.164 g) in 10 mL of anhydrous chloroform was transferred to 3- [2-methyl-5- (4-chlorophenyl) phenyl] -5,5-dimethyl-4-hydroxy-Δ in 10 mL of anhydrous chloroform. After dropwise adding ice-cooling to a solution of 0.4 g of 3 -furan-2-one, the mixture was stirred for 30 minutes with ice-cooling.
    [686] The reaction mixture was then washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution and dried.
    [687] Yield: 0.4 g (72% of theory), log P (pH 2.5) 4.8.
    [688] Similar to Example (I-2-1) and according to the general preparation, compounds of the general formula (I-2) were obtained.
    [689] TABLE B
    [690]
    [691]
    [692]
    [693] logP values were determined in accordance with EEC Directive 79/831 V.A8 by HPLC (high performance liquid chromatography) using a reversed phase column (C 18). Temperature: 43 ° C.
    [694] (a) Mobile phase for determination in acidic range: 0.1% aqueous phosphoric acid, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile.
    [695] (b) mobile phase for measurement in the neutral range: 0.01 molar aqueous phosphate buffer, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile.
    [696] Calibration was performed using unbranched alkan-2-ones (3-16 carbon atoms), where logP values are known (measured logP values by residence time using linear interpolation between two consecutive alkanones).
    [697] UV spectra of 200-400 nm were used to determine the lambda max value as the maximum of the chromatographic signal.
    [698] Example I-3-1
    [699]
    [700] 0.10 ml of sulfuryl chloride in 0.5 ml of anhydrous chloroform was added dropwise to 0.385 g of Example (I-3-a-1) (WO 99/48869) in 10 ml of anhydrous chloroform dropwise with ice cooling. The mixture was stirred for 20 minutes.
    [701] The reaction mixture is washed with NaHCO 3 solution, the organic phase is dried and the solvent is distilled off. For further purification, the product was repeatedly polished with cyclohexane / ethyl acetate.
    [702] Yield: 0.315 g (75% of theory), Melting Point 157-160 ° C.
    [703] Table C
    [704] Similar to Example (I-3-1) and according to the general preparation, compounds of the general formula (I-3) were obtained.
    [705]
    [706] Example A
    [707] Miss Juice Test
    [708] Solvent: Dimethylformamide 7 parts by weight
    [709] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
    [710] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.
    [711] Cabbage leaves ( Brassica oleracea ) heavily infected with peach aphids ( Myzus persicae ) were treated by immersion in the active compound preparation at the desired concentration.
    [712] After a certain period of time, the relief rate was determined in%. 100% means that all the aphids have been killed; 0% means that none of the aphids have been killed.
    [713] In this test, for example, the compounds of the following preparation examples showed good activity:
    [714] Table A
    [715] Plants-Damaged Insects
    [716] Miss Juice Test
    [717]
    [718] Example B
    [719] Phaedon Larva Test
    [720] Solvent: Dimethylformamide 7 parts by weight
    [721] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
    [722] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.
    [723] Cabbage leaves (Brassica oleracea) were treated by immersion in the active compound formulation at the desired concentration, and infected with mustard worms (Phaedon cocleariae) larva while the leaves were damp.
    [724] After a certain period of time, the relief rate was determined in%. 100% means that all mustard larvae have been killed; 0% means that none of the mustard larvae have been killed.
    [725] In this test, for example, the compounds of the following preparation examples showed good activity:
    [726] TABLE B
    [727] Plants-Damaged Insects
    [728] Phaedon Larva Test
    [729]
    [730] Example C
    [731] Flutella test
    [732] Solvent: Dimethylformamide 7 parts by weight
    [733] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
    [734] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.
    [735] Cabbage leaves (Brassica oleracea) were treated by immersion in the active compound formulation at the desired concentration, and infected with cabbage moth (flutella xyllella) caterpillars while the leaves were damp.
    [736] After a certain period of time, the relief rate was determined in%. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
    [737] In this test, for example, the compounds of the following preparation examples showed good activity:
    [738] Table C
    [739] Plants-Damaged Insects
    [740] Flutella test
    [741]
    [742] Example D
    [743] Spodoptera exigua test
    [744] Solvent: Dimethylformamide 7 parts by weight
    [745] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
    [746] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.
    [747] Cabbage leaves (Brassica oleracea) were treated by immersion in the active compound formulation at the desired concentration and infected with matrix maggots (Spodofterra excigua) caterpillars while the leaves were damp.
    [748] After a certain period of time, the relief rate was determined in%. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
    [749] In this test, for example, the compounds of the following preparation examples showed good activity:
    [750] Table D
    [751] Plants-Damaged Insects
    [752] Sportoferra Exigua Exam
    [753]
    [754] Example E
    [755] Spodoptera frugiperda test
    [756] Solvent: Dimethylformamide 7 parts by weight
    [757] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
    [758] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.
    [759] Cabbage leaves (Brassica oleracea) were treated by dipping into active compound formulations of the desired concentration and infected with matrix maggots (Spodoftera pruperperda) caterpillars while the leaves were damp.
    [760] After a certain period of time, the relief rate was determined in%. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
    [761] In this test, for example, the compounds of the following preparation examples showed good activity:
    [762] Table E
    [763] Plants-Damaged Insects
    [764] Spodoptera prugiferda test
    [765]
    [766] Example F
    [767] Tetranicus Test (OP-Resistant / Immersed)
    [768] Solvent: Dimethylformamide 7 parts by weight
    [769] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
    [770] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.
    [771] Soybean plants (Phaseus vulgaris ) heavily infected with spotted mites of all stages ( Tetranychus urticae ) were treated by immersion in the active compound preparation at the desired concentration.
    [772] After a certain period of time, the relief rate was determined in%. 100% means that all the spots have been killed; 0% means that none of the mites have been killed.
    [773] In this test, for example, the compounds of the following preparation examples showed good activity:
    [774] TABLE F
    [775] Plants-Damaged Insects
    [776] Tetranicus Test (OP-Resistant / Immersed)
    [777]
    [778] Example G
    [779] In vitro test for determination of ED 50 in microorganisms
    [780] A methanol solution of the active compound to be tested, mixed with emulsifier PS16, was pipetted into a microtiter plate well. After solvent evaporation, 200 μl of potato / dextrose medium was added to each well.
    [781] In advance, an appropriate concentration of fungal spores or mycelium to be tested was added to the medium.
    [782] Active compound concentrations are 0.1, 1, 10 and 100 ppm. Emulsifier concentration is 300 ppm.
    [783] Plates were then incubated on a stirrer for 3-5 days at a temperature of 22 ° C. until sufficient proliferation could be observed in the untreated control.
    [784] Evaluation was carried out by photometric measurement at 620 nm wavelength. From the data measured at different concentrations, the dose of the active compound (ED 50 ) that inhibits fungal growth 50% for the untreated control was calculated.
    [785] Table G
    [786] In vitro test for determination of ED 50 in microorganisms
    [787] Active compoundmicrobeED 50Example I-3-1Botrytis Cinereapyulicaria Orissaepceptoria Tritisiustilago Avena<0.10 <0.100.610.27
    [788] Example H
    [789] Post Germination Test
    [790] Solvent: 5 parts by weight of acetone
    [791] Emulsifier: 1 part by weight of alkylaryl polyglycol ether
    [792] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvent in the amounts mentioned above, adding the above mentioned amount of emulsifier and then diluting the concentrate with water to the desired concentration.
    [793] Test plants 5 to 15 cm tall were sprayed with the active compound formulation to apply a specific amount of the desired active compound per unit area. The concentration of the spray liquid was chosen so that a specific amount of the desired active compound was applied at 1000 L / ha of water.
    [794] After 3 weeks, the degree of damage of the plants was recorded as% damage compared to the development of the untreated control.
    [795] The figures represent the following:
    [796] 0% = no effect (same as untreated control)
    [797] 100% = complete control
    [798] Example I
    [799] Germination test
    [800] Solvent: 5 parts by weight of acetone
    [801] Emulsifier: 1 part by weight of alkylaryl polyglycol ether
    [802] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvent in the amounts mentioned above, adding the above mentioned amount of emulsifier and then diluting the concentrate with water to the desired concentration.
    [803] Seeds of the test plants were sown on top soil. After about 24 hours, the soil was sprayed with the active compound formulation in each case so that a specific amount of the desired active compound per unit area was applied. The concentration of the spray was chosen so that a specific amount of the desired active compound was applied at 1000 L / dl of water.
    [804] After 3 weeks, the degree of damage of the plants was recorded as% damage compared to the development of the untreated control.
    [805] The figures represent the following:
    [806] 0% = no effect (same as untreated control)
    [807] 100% = complete control
    [808] Germination / GreenhouseActive ingredient g / ㏊AllopecurusAvenapatuaEchinokloaSetariaAmaranthus Example I-1-4250959010010090
    [809] After germination / greenhouseActive ingredient g / ㏊sugar beetAllopecurusAvenapatuaEchinokloaSetaria Example I-1-4 Example I-1-1125025000809510090100100100100
    [810] After germination / greenhouseActive ingredient g / ㏊AllopecurusAvenapatuaEchinokloaSetaria Example I-1-7 Example I-1-9 Example I-1-13250 250 250909595951009010010010010010090
    [811] After germination / greenhouseActive ingredient g / ㏊sugar beetAllopecurusAvenapatuaDigitariaEchinokloaSetaria Example I-1-2 Example I-1-1125125009095951001009010010090100
    [812] After germination / greenhouseActive ingredient g / ㏊AllopecurusAvenapatuaEchinokloaSetariaAmaranthusSinapis Example I-1-6 Example I-1-8 Example I-1-10 Example I-1-4250 250 250 25070951001001009510010010010010010095100100100707080--808070
    [813] Example J
    [814] Plasmopara test (vine) / protection
    [815] Solvent: 24.5 parts by weight of acetone
    [816] 24.5 parts by weight of dimethylacetamide
    [817] Emulsifier: 1.0 parts by weight of alkylaryl polyglycol ether
    [818] 1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
    [819] To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. After drying of the spray coating, the plants were inoculated with an aqueous spore suspension of Plasmopara viticola and then placed in the inoculation chamber at 20 ° C. and 100% relative atmospheric humidity for one day. The plants were then left in the greenhouse at about 21 ° C. and about 90% relative atmospheric humidity for 4 days. The plants were then wetted and left in the inoculation room for one day.
    [820] Evaluation was performed 6 days after the inoculation. 0% means efficiency corresponding to the control; An efficiency of 100% means that no infection was observed.
    [821] Table J
    [822] Plasmopara test (vine) / protection
    [823]
    [824] Example K
    [825] Venturi Test (Apple) / Protection
    [826] Solvent: 24.5 parts by weight of acetone
    [827] 24.5 parts by weight of dimethylacetamide
    [828] Emulsifier: 1.0 parts by weight of alkylaryl polyglycol ether
    [829] 1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
    [830] To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. After drying of the spray coating, the plants were inoculated with an aqueous conidia suspension of Venturia naciqualis, the causative agent of apple strains, and then placed in an incubation chamber at about 20 ° C. and 100% relative atmospheric humidity for one day.
    [831] The plants were then placed in a greenhouse at about 21 ° C. and about 90% relative atmospheric humidity.
    [832] Evaluation was carried out 10 days after the inoculation. 0% means efficiency corresponding to the control; An efficiency of 100% means that no infection was observed.
    [833] Table K
    [834] Venturi Test (Apple) / Protection
    [835]
    [836] Example L
    [837] Critical Concentration Test / Soil Insect-Treatment of Transgenic Plants
    [838] Test insect: Diabrotica balteata -larvae in soil
    [839] Solvent: 7 parts by weight of acetone
    [840] Emulsifier: 1 part by weight of alkylaryl polyglycol ether
    [841] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvent in the amounts mentioned above, adding the above mentioned amount of emulsifier and then diluting the concentrate with water to the desired concentration.
    [842] The active compound formulation is poured into the soil. At this time, the active compound concentration in the formulation is of no practical importance, only the weight of the active substance applied in soil (ppm (mg / l)) is the key. The soil was charged to a 0.25 L pot and left at 20 ° C.
    [843] Immediately after preparation, five germinated corn kernels of YIELD GUARD varieties (trademark of Monsanto Comp., USA) were introduced into each pot. After two days, the test insect was placed in the treated soil. Seven days later, the number of germinated corn plants was counted to determine the efficiency of the active compound (one plant = 20% active).
    [844] Example M
    [845] Heliothis virescens test-treatment of transgenic plants
    [846] Solvent: 7 parts by weight of acetone
    [847] Emulsifier: 1 part by weight of alkylaryl polyglycol ether
    [848] A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents mentioned above and adding the aforementioned amount of emulsifier and then diluting the concentrate with water to the desired concentration.
    [849] Soybean sprigs ( Glycine max ) from the Roundup Ready variety (trademark of Monsanto Comp., USA) were immersed in an active compound formulation of the desired concentration and infected with tobacco shoots Heliotis viresense while the leaves were moist. I was.
    [850] After a certain period of time, the control rates of insects were determined.
    权利要求:
    Claims (13)
    [1" claim-type="Currently amended] Compound of Formula (I):

    Where
    Q represents oxygen, sulfur or group N-D,
    X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro, cyano or optionally substituted phenyl,
    Y represents in each case optionally substituted aryl or hetaryl,
    W and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano,
    A represents hydrogen or, in each case, saturated or unsaturated cycloalkyl, optionally substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, or optionally at least one ring atom is replaced by a hetero atom and optionally substituted Or in each case optionally represents halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl,
    B represents hydrogen, alkyl or alkoxyalkyl, or
    A and B, together with the carbon atoms to which they are attached, represent a cycle, optionally containing at least one hetero atom, saturated or unsaturated, unsubstituted or substituted,
    D represents hydrogen or alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, arylalkyl, aryl, het, wherein one or more ring members are optionally replaced by heteroatoms An optionally substituted radical selected from the group consisting of arylalkyl and hetaryl,
    A and D together with the atoms to which they are attached represent a saturated or unsaturated ring in which the A, D moiety is unsubstituted or substituted and optionally contains at least one heteroatom,
    G represents halogen or nitro.
    [2" claim-type="Currently amended] The method of claim 1,
    Q represents oxygen, sulfur or group N-D,
    W represents hydrogen, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy,
    X represents halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy or cyano, or optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -haloalkoxy-, nitro- or cyano-substituted phenyl,
    Y represents one of the following radicals:

    V 1 is hydrogen, halogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Phenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, nitro or cyano or halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 - indicates a or disubstituted phenyl, -haloalkyl, C 1 -C 4 - haloalkoxy, nitro or by cyano, optionally one
    V 2 and V 3 independently of one another represent hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy,
    Z represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, nitro or cyano,
    A is in each case optionally halogen-substituted C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, C 1 -C 10 -alkoxy-C 1 -C 8 -alkyl, poly-C 1 -C 8 -Alkoxy-C 1 -C 8 -alkyl or C 1 -C 10 -alkylthio-C 1 -C 6 -alkyl, or optionally one or two directly non-adjacent ring members are replaced by oxygen and / or sulfur Substituted and optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl, or in each case optionally halogen-, C 1 -C 6- Alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, cyano- or nitro-substituted phenyl or phenyl-C 1 -C 6- Alkyl or, in the case of group (I-1), hydrogen when D is not hydrogen,
    B represents hydrogen, C 1 -C 12 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, or
    A, B and the carbon atom to which they are attached are optionally substituted with one ring member by oxygen or sulfur and C 1 -C 8 -alkyl, C 3 -C 10 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 8 - alkoxy, C 1 -C 8 - alkylthio, one phenyl optionally by halogen or - mono-or di-saturated C 3 -C 10 - cycloalkyl or unsaturated C 5 -C 10 -, or represent cycloalkyl,
    A, B and the carbon atoms to which they are attached are further 5- to 8-membered by alkylenediyl groups, optionally containing one or two directly non-contiguous oxygen and / or sulfur atoms, or together with the carbon atoms bonded thereto. C 3 -C 6 -cycloalkyl substituted by an alkylenedioxyl or alkylenedithioyl group forming a ring, or
    A, B and the carbon atom to which they are attached are the two substituents together with the carbon atom to which they are attached, in each case optionally C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy- or halogen-substituted and optionally one the methylene group is a C 2 -C 6 replaced by an oxygen or sulfur-alkanediyl, C 2 -C 6 al canned yl or C 4 -C 6 - cycloalkyl-C 3 -C 8 alkane representing one diendi Or C 5 -C 8 -cycloalkenyl,
    D represents hydrogen, or in each case optionally halogen-substituted C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 1 -C 10 -alkoxy-C 2 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl or C 1 -C 10 -alkylthio-C 2 -C 8 -alkyl, or optionally one ring member Is substituted by oxygen or sulfur and optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkyl Or optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, cyano- or nitro -Represents substituted phenyl, or
    A and D together is optionally substituted in each case optionally one methylene group is a C 3 -C 6 replaced by an oxygen or sulfur-indicates the Al canned work-alkanediyl or C 3 -C 6
    Possible substituents in each case are C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or additional C 3 -C 6 -alkanediyl groups,
    G is a compound of formula (I) representing chlorine, bromine or nitro.
    [3" claim-type="Currently amended] The method of claim 1,
    Q represents oxygen, sulfur or group N-D,
    W represents hydrogen, chlorine, bromine or C 1 -C 4 -alkyl,
    X represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or nitro,
    Y is radical
    Indicates
    V 1 represents hydrogen, fluorine, chlorine, bromine, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, nitro or cyano Or optionally by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, nitro or cyano Mono- or disubstituted phenyl,
    V 2 represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy,
    Z represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkoxy,
    A represents C 1 -C 10 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, optionally substituted by fluorine or chlorine, respectively, or optionally one ring member is oxygen or sulfur Denotes C 3 -C 7 -cycloalkyl substituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or each of fluorine, chlorine, bromine, Phenyl or phenyl-C 1 -C 2 optionally mono- or disubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy -Alkyl, or in the case of group (I-1) hydrogen when D is not hydrogen,
    B represents hydrogen or C 1 -C 6 -alkyl, or
    A, B and the carbon atoms to which they are attached optionally have one ring member replaced by oxygen or sulfur, C 1 -C 6 -alkyl, C 5 -C 6 -cycloalkyl, C 1 -C 3 -haloalkyl, Saturated C 3 -C 8 -cycloalkyl optionally mono- or disubstituted by C 1 -C 6 -alkoxy, fluorine, chlorine or phenyl, provided that D in group (I-1) is hydrogen or C 1 -C 4 -alkyl,
    D represents hydrogen or C 1 -C 10 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 4- , optionally substituted by fluorine or chlorine, respectively Alkyl or C 1 -C 4 -alkylthio-C 2 -C 4 -alkyl, or optionally one methylene group is replaced by oxygen or sulfur and substituted with fluorine, chlorine, C 1 -C 4 -alkyl, C 1- C 3 -C 7 -cycloalkyl optionally mono- or di-substituted by C 4 -alkoxy or C 1 -C 2 -haloalkyl, or represent fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1- Phenyl optionally mono- or disubstituted by C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, or
    A and D together represent C 3 -C 5 -alkanediyl, optionally substituted by one methylene group and replaced by oxygen or sulfur, where possible substituents are C 1 -C 4 -alkyl,
    G is a compound of formula (I) representing chlorine, bromine or nitro.
    [4" claim-type="Currently amended] The method of claim 1,
    Q represents oxygen, sulfur or group N-D,
    W represents hydrogen, chlorine, methyl or ethyl,
    X represents chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
    Y is radical
    Indicates
    V 1 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, trifluor Chloromethyl, trifluoromethoxy, nitro or cyano,
    V 2 represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
    Z represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl or methoxy,
    A represents C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl or C 3 -C 6 -cycloalkyl, optionally in which one ring member is replaced by oxygen or sulfur; , For group (I-1) represents hydrogen when D is not hydrogen,
    B represents hydrogen, methyl or ethyl, or
    A, B and the carbon atoms to which they are attached optionally have one ring member replaced by oxygen or sulfur, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, trifluoromethyl , Saturated C 3 -C 8 -cycloalkyl optionally substituted by methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, in which case group (I-1 D) represents hydrogen or C 1 -C 3 -alkyl,
    D represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopentyl or cyclohexyl, or
    A and D together represent C 3 -C 4 -alkanediyl, optionally substituted by one carbon atom by oxygen or sulfur,
    G is a compound of formula (I) representing chlorine or nitro.
    [5" claim-type="Currently amended] The method of claim 1,
    Q represents group N-D,
    W represents hydrogen, chlorine or methyl,
    X represents chlorine, methyl or ethyl,
    Y is radical
    Indicates,
    V 1 represents chlorine or methyl,
    V 2 represents hydrogen or chlorine,
    Z represents hydrogen or methyl,
    A represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
    B represents methyl, or
    A, B and the carbon atoms to which they are attached optionally have one ring member replaced by oxygen or sulfur and by methyl or in the case of C 6 -cycloalkyl also ethyl, n-propyl, isopropyl, n-butyl, iso Saturated C 3 -C 8 -cycloalkyl optionally substituted by butyl, t-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy ,
    D represents hydrogen,
    G is a compound of formula (I) representing chlorine or nitro.
    [6" claim-type="Currently amended] The method of claim 1,
    Q represents oxygen,
    W represents hydrogen, chlorine or methyl,
    X represents chlorine, methyl or ethyl,
    Y is radical
    Indicates,
    V 1 represents chlorine, fluorine, cyano or methyl,
    V 2 represents hydrogen or chlorine,
    Z represents hydrogen or methyl,
    A represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
    B represents methyl, or
    A, B and the carbon atoms to which they are attached optionally have one ring member replaced by oxygen or sulfur, by methyl or in the case of C 6 -cycloalkyl also ethyl, n-propyl, isopropyl, n-butyl, iso Saturated C 3 -C 8 -cycloalkyl optionally substituted by butyl, t-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy ,
    G is a compound of formula (I) representing chlorine.
    [7" claim-type="Currently amended] The method of claim 1,
    Q represents sulfur,
    W represents hydrogen,
    X represents chlorine or methyl,
    Y is radical
    Indicates,
    Z represents hydrogen or methyl,
    A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 -cycloalkyl, optionally substituted by one ring member by oxygen, optionally substituted by methyl or methoxy,
    G is a compound of formula (I) representing chlorine.
    [8" claim-type="Currently amended] A) The compounds of the general formulas (II-1) to (II-3) are reacted with a halogenating agent in the presence of a solvent and optionally in the presence of a free-radical initiator to react the general formulas (I-1) to (I-3) To obtain a compound of
    B) reacting the compounds of formulas (II-1) to (II-3) with a nitrating agent in the presence of a solvent to obtain compounds of formulas (I-1) to (I-3) Method for preparing a compound of formula (I) according to claim 1:


    Where
    A, B, Q, W, X, Y and Z are as defined in claim 1,
    In method A) G stands for halogen,
    In method B) G stands for nitro.
    [9" claim-type="Currently amended] A pesticide and / or herbicide and / or fungicide comprising at least one compound of formula (I) according to claim 1.
    [10" claim-type="Currently amended] A method for controlling animal pests and / or unwanted plants and / or fungi, characterized by acting on the pests and / or their habitats according to claim 1.
    [11" claim-type="Currently amended] Use of a compound of formula (I) according to claim 1 for controlling animal pests and / or unwanted plants and / or fungi.
    [12" claim-type="Currently amended] A process for preparing pesticides and / or herbicides and / or fungicides, characterized in that the compound of formula (I) according to claim 1 is mixed with an extender and / or a surfactant.
    [13" claim-type="Currently amended] Use of a compound of formula (I) according to claim 1 for the preparation of pesticides and / or herbicides and / or fungicides.
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    同族专利:
    公开号 | 公开日
    US7307044B2|2007-12-11|
    ES2368037T3|2011-11-11|
    KR100940777B1|2010-02-11|
    BR0214524A|2004-11-03|
    US20120028804A1|2012-02-02|
    WO2003045957A1|2003-06-05|
    US8119570B1|2012-02-21|
    DE10158560A1|2003-06-12|
    US20100173778A1|2010-07-08|
    US20050090400A1|2005-04-28|
    AU2002356616A1|2003-06-10|
    JP4538223B2|2010-09-08|
    AT517110T|2011-08-15|
    JP2005516906A|2005-06-09|
    CA2468422A1|2003-06-05|
    US7928037B2|2011-04-19|
    EP1451195A1|2004-09-01|
    MXPA04005074A|2004-08-19|
    CN1285597C|2006-11-22|
    CN1615311A|2005-05-11|
    EP1451195B1|2011-07-20|
    TW200303859A|2003-09-16|
    AR037445A1|2004-11-10|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    2001-11-29|Priority to DE10158560A
    2001-11-29|Priority to DE10158560.8
    2002-11-18|Application filed by 바이엘 크롭사이언스 아게
    2002-11-18|Priority to PCT/EP2002/012881
    2004-07-03|Publication of KR20040058302A
    2010-02-11|Application granted
    2010-02-11|Publication of KR100940777B1
    优先权:
    申请号 | 申请日 | 专利标题
    DE10158560A|DE10158560A1|2001-11-29|2001-11-29|3-biphenyl-substituted-3-substituted-4-ketolactams and lactones|
    DE10158560.8|2001-11-29|
    PCT/EP2002/012881|WO2003045957A1|2001-11-29|2002-11-18|3-biphenyl-substituted-3-substituted-4-ketolactam and ketolactone and their utilization as pesticide|
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