TW201531226A - Benzocyclobutane(thio) carboxamides - Google Patents

Abstract

The present invention relates to novel benzocyclobutane(thio) carboxamides, to processes for preparing these compounds, to compositions comprising these compounds, The present invention relates to novel benzocyclobutane(thio) carboxamides, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials.

Description

Benzocyclobutane (thio)carboxamide

The present invention relates to novel benzocyclobutane (thio)carboxamides, processes for preparing these compounds, compositions comprising these compounds and their use as biologically active compounds, particularly for crop protection and material protection Use for the control of harmful microorganisms.

It is known that certain indoline carbamazepines have fungicidal properties (for example, WO 1992/12970, EP-A 0199822, EP-A 0276177, JP-A 62-096472, JP-A 05-310512, JP-A 01-313402, WO 2002/059086, WO 2004/103975 and J. Org . Chem . 1995 , 60 , 1626-1631).

Specific tetrahydronaphthylcarboxamides are also known (J. Pesticide Sci. 18, 49-57, 1993 , WO 2012/065945, WO 2002/096882). WO 2004/103975 generally describes iodopyrazole tetrahydronaphthylcarboxamide without mentioning specific examples.

Because of the ecological and economic requirements for modern active ingredients such as fungicides, such as activity profile, toxicity, selectivity, application rate, residue formation and advantageous manufacturing, for development at least in certain There is a continuing need in the field for novel fungicidal compositions that have advantages over known compositions.

The present invention provides novel benzocyclobutane (thio)carboxamides of formula (I), Wherein the Ar system represents a group selected from the group consisting of Ar1 to Ar15: X ¹ , X ² , X ³ , X ⁴ and X ⁵ independently represent hydrogen; halogen; cyano; nitro, hydroxy; C ₁ -C ₁₆ -alkyl, having from 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl; C ₃ -C ₇ - cycloalkyl, having from 1 to 9 identical or different halogen atoms C ₃ -C ₇ - cycloalkyl, halogen; C ₁ -C ₆ - alkoxy a C ₁ -C ₆ -haloalkoxy group having 1 to 9 identical or different halogen atoms; a T system representing an oxygen or sulfur atom; and a Q system representing hydrogen, a C ₁ -C ₆ -alkylsulfonyl group, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl; X represents halogen, nitro, cyano C ₁ -C ₁₂ -alkyl; C ₁ -C ₆ -haloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ - Alkoxy; C ₁ -C ₆ -haloalkoxy having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ -alkylsulfanyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl sulfanyl; C ₁ -C ₆ - alkylsulfinyl acyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - alkylsulfinyl acyl halide ; C ₁ -C ₆ - alkylsulfonyl ; Having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl sulfo acyl; C ₂ -C ₁₂ - alkenyl; C ₂ -C ₁₂ - alkynyl; C ₃ -C ₇ - cycloalkyl Alkyl; phenyl; tri(C ₁ -C ₈ )alkylindenyl; tri(C ₁ -C ₈ )alkylindolyl-C ₁ -C ₈ -alkyl; m represents 0, 1, 2 or 3; R ¹ , R ² , R ³ and R ⁴ independently of each other represent hydrogen; halogen; C ₁ -C ₁₆ -alkyl; C ₂ -C ₁₆ -halane having 1 to 9 identical or different halogen atoms C ₃ -C ₈ -cycloalkyl; C ₃ -C ₇ -halocycloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ having 1 to 9 identical or different halogen atoms -haloalkyl; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyl; (C ₃ -C ₈ -cycloalkyl)-C ₃ -C ₈ -cycloalkyl; C ₂ -C ₁₆ -alkenyl; C ₂ -C ₁₆ -alkynyl; C ₂ -C ₁₆ -alkenyl-C ₁ -C ₁₆ -alkyl; C ₂ -C ₁₆ -alkynyl-C ₁ -C ₁₆ -alkane C ₁ -C ₁₆ -alkoxy; C ₃ -C ₈ -cycloalkyloxy; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyloxy; C ₁ - C ₈ -alkylsulfanyl; C ₃ -C ₈ -cycloalkylsulfanyl; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkylsulfanyl; C ₂ -C ₁₆ -alkenyloxy; C ₃ -C ₈ - alkynyloxy; aryl substituted by up to 6 identical or different R ^b groups, if desired; aryl-C ₁ -C ₈ - substituted with up to 6 identical or different R ^b groups alkyl group; aryl group optionally substituted -C ₁ -C ₈ High 6 are the same or different R ^b groups of - alkylsulfanyl; an optionally-high six identical or different R ^b groups Substituted aryloxy; arylsulfanyl substituted by up to 6 identical or different R ^b groups; (C ₃ -C ₈ -cycloalkyl)-C ₂ -C ₈ -alkenyl; C ₃ -C ₈ -cycloalkyl)-C ₂ -C ₈ -alkynyl; tris(C ₁ -C ₈ )alkylindenyl; tris(C ₁ -C ₈ )alkylindenyl-C ₁ -C ₈ - alkyl; optionally substituted six-high of the same or different R ^b groups aryl -C ₁ -C ₈ - alkyl; optionally substituted aryl-high six identical or different R ^b groups of a aryl-C ₂ -C ₈ -alkenyl group; an aryl-C ₂ -C ₈ -alkynyl group substituted with up to 6 identical or different R ^b groups as desired; the limiting conditions are R ¹ , R ² , R ³ and R ⁴ do not simultaneously represent a carbon or hydrogen R ¹ and R ² lines connected thereto together represent a C ₃ -C ₈ - cycloalkyl; C ₃ -C ₈ - cycloalkenyl, each optionally Department Substituted or R ¹ and R ² are representatives = C (Y ¹⁾ Y ² group or R ¹ and R ² are representatives containing 51 or two hetero atoms or a 6-membered ring and / or R ³ and R ⁴ Line and The linked carbons together represent a C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl group, each of which is optionally substituted or the R ³ and R ⁴ systems represent =C(Y ¹ )Y ² The group and/or R ³ and R ⁴ represent a 5- or 6-membered ring containing 1 or 2 heteroatoms or the R ¹ and R ³ systems together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group, C ₃ -C ₈ -cycloalkenyl, each of which is optionally substituted; R ^b represents halogen; nitro, cyano, C ₁ -C ₁₂ -alkyl; having from 1 to 9 identical or different halogen atoms C ₁ -C ₆ -haloalkyl; C ₁ -C ₆ -alkoxy having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ -haloalkoxy; C ₁ -C ₆ -alkane ylsulfanyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl sulfanyl; C ₁ -C ₆ - alkylsulfonyl group; having 1 to 9 identical or different halogen C ₁ -C ₆ -haloalkylsulfonyl; C ₂ -C ₁₂ -alkenyl; C ₂ -C ₁₂ -alkynyl; C ₃ -C ₇ -cycloalkyl;phenyl; tri(C ₁ -C ₈ )alkyl fluorenyl; tris(C ₁ -C ₈ ) Alkyl silicon based -C ₁ -C ₈ - alkyl; the Y ¹ and Y ² independently of one another train represents hydrogen, halogen, C ₁ -C ₁₂ - alkyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ -haloalkyl; C ₁ -C ₈ -alkylsulfanyl; phenyl; each of which is optionally substituted; or Y ¹ and Y ² may form a C ₃ -C together with the carbon to which they are attached ₈ -cycloalkyl or mono-C ₃ -C ₈ -cycloalkenyl or a saturated 5, 6 or 7-membered heterocyclic ring; each of which is optionally substituted.

Preferred embodiment

Formula (I) provides a general definition of the benzocyclobutane (thio)carboxamides of the present invention. Preferred group definitions for the formulas above and below are as follows. These definitions apply to the final product of formula (I) and to all intermediates as well.

Ar preferably represents a group selected from the group consisting of Ar1, Ar2, Ar4, Ar7, Ar8, Ar10 and Ar13 groups.

Ar Tejia is representative of the groups selected from the following: Ar1, Ar2 and Ar4 groups.

The Ar optimal system represents a group selected from the Ar2 and Ar4 groups.

X ¹ preferably represents halogen; C ₁ -C ₁₆ -alkyl, C ₁ -C ₆ -haloalkyl having 1 to 9 of the same or different halogen atoms; C ₃ -C ₇ -cycloalkyl, having 1 to 9 C ₃ -C ₇ -halocycloalkyl groups of the same or different halogen atoms.

X ¹ particularly preferably represents a C ₁ -C ₁₂ -alkyl group, a C ₁ -C ₄ -haloalkyl group having 1 to 9 identical or different halogen atoms.

X ¹ very particularly preferably represents methyl, ethyl, difluoromethyl, trifluoromethyl, iodine.

X ^{1 is} most preferably a difluoromethyl group.

X ² , X ³ , X ⁴ and X ⁵ independently of one another preferably represent hydrogen, halogen, C ₁ -C ₁₆ -alkyl, C ₁ -C ₆ -halane having from 1 to 9 identical or different halogen atoms group; C ₃ -C ₇ - cycloalkyl, having from 1 to 9 identical or different halogen atoms C ₃ -C ₇ - cycloalkyl halides.

X ² , X ³ , X ⁴ and X ⁵ particularly preferably independently of each other represent hydrogen, fluorine, chlorine, bromine, iodine; C ₁ -C ₁₂ -alkyl, C having from 1 to 9 identical or different halogen atoms ₁ -C ₄ -haloalkyl.

X ² , X ³ , X ⁴ and X ⁵ very particularly independently represent hydrogen, fluorine, chlorine, bromine, iodine, methyl or ethyl.

X ² , X ³ , X ⁴ and X ^{5 are} preferably independently of each other and represent fluorine or chlorine.

T preferably represents an oxygen atom.

Q preferably represents hydrogen, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₁ -C ₄ -haloalkylsulfonium a halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl group having 1 to 9 fluorine, chlorine and/or bromine atoms.

Q particularly preferred is hydrogen, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, second- or tert-butylsulfonyl, methoxy Methyl, methoxyethyl, ethoxymethyl, ethoxyethyl, trifluoromethylsulfonyl, trifluoromethoxymethyl.

The Q best system represents hydrogen.

X preferably represents fluorine, chlorine, methyl or trifluoromethyl.

X particularly preferred represents fluorine, wherein the fluorine is preferably at the 4-, 5- or 6-position of the benzocyclobutane group, very particularly preferably at the 4- or 6-position.

X is more particularly representative of chlorine, wherein the chloroform is located at the 4-, 5- or 6-position of the benzocyclobutane group, very particularly preferably at the 4- or 6-position.

Further preferably, X represents a methyl group, wherein the methyl group is preferably at the 4-, 5- or 6-position of the benzocyclobutane group, very particularly preferably at the 4- or 6-position.

Further preferably, X represents a trifluoromethyl group, wherein the trifluoromethyl group is preferably located at the 4-, 5- or 6-position of the benzocyclobutane group, very particularly preferably at the 4- or 6-position. -position.

m preferably represents 0, 1 or 2.

m particularly preferred represents 0 or 1.

The m best system represents 0.

R ¹ , R ² , R ³ and R ⁴ independently of each other preferably represent hydrogen; halogen; C ₁ -C ₁₆ -alkyl; C ₂ -C ₁₆ -halide having 1 to 9 identical or different halogen atoms Alkyl; C ₃ -C ₈ -cycloalkyl; C ₃ -C ₇ -halocycloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C having 1 to 9 identical or different halogen atoms ₆ -haloalkyl; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyl; (C ₃ -C ₈ -cycloalkyl)-C ₃ -C ₈ -cycloalkyl; C ₁ -C ₁₆ -alkoxy; C ₃ -C ₈ -cycloalkyloxy; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyloxy; up to 6 as needed the substituents R ^b identical or different aryl group; optionally substituted six-high of the same or different R ^b groups aryl -C ₁ -C ₈ by - an alkyl group; an optionally-high six identical Or an aryl-C ₁ -C ₈ -alkyl group substituted with a different R ^b group; the limitation is that R ¹ , R ² , R ³ and R ⁴ cannot simultaneously represent hydrogen.

R ¹ , R ² , R ³ and R ⁴ independently of each other particularly preferably represent hydrogen; halogen; C ₁ -C ₁₆ -alkyl; C ₂ -C ₁₆ -halide having 1 to 9 identical or different halogen atoms Alkyl; C ₃ -C ₈ -cycloalkyl; C ₃ -C ₇ -halocycloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C having 1 to 9 identical or different halogen atoms ₆ -haloalkyl; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyl; (C ₃ -C ₈ -cycloalkyl)-C ₃ -C ₈ -cycloalkyl; C ₁ -C ₁₆ - alkoxy; optionally substituted six-high identical or different R ^b groups of the aryl group; optionally substituted six-high identical or different R ^b groups of the aryl group -C ₁ - C ₈ -alkyl; which is limited to the fact that R ¹ , R ² , R ³ and R ⁴ cannot simultaneously represent hydrogen.

R ¹ , R ² , R ³ and R ⁴ independently represent each other independently hydrogen; phenyl, ethyl, methyl, prop-2-yl; the restrictions are R ¹ , R ² , R ³ and R ⁴ can not represent hydrogen at the same time.

R ¹ and R ² preferably together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group which may be optionally substituted, wherein the substituent may be selected from a halogen and a C ₁ -C ₆ -alkyl group.

R ¹ and R ² particularly preferably together with the carbon to which they are attached represent a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group which may be optionally substituted, wherein the substituent may be selected from the group consisting of fluorine, chlorine and methyl. And ethyl.

R ³ and R ⁴ preferably together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group which may be optionally substituted, wherein the substituent may be selected from a halogen and a C ₁ -C ₆ -alkyl group.

R ³ and R ⁴ particularly preferably together with the carbon to which they are attached represent a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group which may be optionally substituted, wherein the substituent may be selected from the group consisting of fluorine, chlorine and methyl. And ethyl.

R ³ and R ^{4 are} preferably together with the carbon to which they are attached represent a cyclopentyl or cyclohexyl group.

R ¹ and R ³ preferably together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group which may be optionally substituted, wherein the substituent may be selected from a halogen and a C ₁ -C ₆ -alkyl group.

Y ¹ and Y ² preferably independently of each other represent hydrogen or a halogen, a C ₁ -C ₁₂ -alkyl group, or a C ₁ -C ₆ -haloalkyl group having from 1 to 9 of the same or different halogen atoms. The carbons together form a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl group which is optionally substituted.

Y ¹ and Y ² particularly preferably independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl; ethyl, propyl, isopropyl.

R ^b preferably represents halogen, nitro, cyano, C ₁ -C ₈ -alkyl; C ₁ -C ₄ -haloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ Alkoxy; C ₁ -C ₄ -haloalkoxy having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ -alkylsulfanyl; having 1 to 9 identical or different halogen atoms the C ₁ -C ₄ - haloalkyl sulfanyl; C ₁ -C ₆ - alkylsulfonyl group; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ - haloalkyl sulfo acyl; C ₂ -C ₈ -alkenyl; C ₂ -C ₈ -alkynyl; C ₃ -C ₆ -cycloalkyl;phenyl;tri(C ₁ -C ₆ )alkylindenyl; tris(C ₁ -C ₆ ) Alkylmercapto-C ₁ -C ₆ -alkyl.

R ^b particularly preferably represents fluorine, chlorine, bromine; C ₁ -C ₆ -alkyl; C ₁ -C ₄ -haloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C ₄ -alkane An oxy group; a C ₁ -C ₄ -haloalkoxy group having 1 to 9 identical or different halogen atoms; a C ₁ -C ₄ -alkylsulfanyl group; C having 1 to 9 identical or different halogen atoms ₁ -C ₄ - haloalkyl sulfanyl; C ₁ -C ₄ - alkylsulfonyl group; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ - haloalkyl sulfo acyl; ₂ C -C ₆ -alkenyl; C ₂ -C ₆ -alkynyl; C ₃ -C ₆ -cycloalkyl; phenyl; tri(C ₁ -C ₄ )alkylindenyl; tris(C ₁ -C ₄ ) Alkylmercapto-C ₁ -C ₄ -alkyl.

R ^b is very particularly representative of fluorine, chlorine, bromine; methyl, ethyl, n-propyl, isopropyl, n-, i-, second-, tri-butyl, trifluoromethyl, tri Chloromethyl, difluoromethyl, methoxy, trifluoromethoxy, methylsulfanyl, trifluoromethylsulfanyl, vinyl, allyl, ethynyl, propargyl, cyclopropyl , phenyl, trimethyl fluorenyl.

Unless otherwise indicated, a substituted group or substituent according to the invention is substituted with one or more groups selected from the group consisting of: halogen; nitro, cyano, C ₁ -C ₁₆ -alkane group; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl; C ₁ -C ₆ - alkoxy; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkoxy; C ₁ -C ₆ - alkyl sulfanyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl sulfanyl; C ₁ -C ₆ - alkyl Sulfhydryl; C ₁ -C ₆ -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C ₂ -C ₁₂ -alkenyl; C ₂ -C ₁₂ -alkynyl; C ₃ -C ₇ -cycloalkyl; phenyl; tri(C ₁ -C ₈ )alkylindenyl; tri(C ₁ -C ₈ )alkylindolyl-C ₁ -C ₈ -alkyl.

Finally, it has been found that the novel (thio)carboxamides of formula (I) have very good microbicidal properties and can be used to control unwanted microorganisms in crop protection and material protection.

The definition of C ₁ -C ₁₆ -alkyl includes the definition of the maximum range of alkyl groups herein. In particular, this definition includes the meanings of methyl, ethyl, n-, isopropyl, n-, i-, second-, and tri-butyl, and in each case all isomers of pentyl, Hexyl, heptyl, octyl, decyl, decyl, eleven, twelve, thirteen, fourteen, fifteen, and sixteen. A preferred range is C ₂ -C ₁₂ -alkyl, such as ethyl and straight or branched propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, decyl, undecyl and a dodecyl group, especially a linear or branched C ₃ -C ₁₀ -alkyl group, such as propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethyl Propyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl Pentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethyl Butyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl , 1-ethyl-3-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, 1- Methyl heptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1-propylpentyl, 2-propylpentyl, decyl, 1-methyloctyl, 2- Methyl octyl Base, 1-ethylheptyl, 2-ethylheptyl, 1-propylhexyl, 2-propylhexyl, decyl, 1-methylindolyl, 2-methylindolyl, 1-ethyloctyl Base, 2-ethyloctyl, 1-propylheptyl and 2-propylheptyl, especially propyl, 1-methylethyl, butyl, 1-methylbutyl, 2-methylbutyl Base, 3-methylbutyl, 1,1-dimethylethyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, pentyl, 1-methylbutyl, 1 -ethylpropyl, hexyl, 3-methylpentyl, heptyl, 1-methylhexyl, 1-ethyl-3-methylbutyl, 1-methylheptyl, 1,2-dimethyl Hexyl, 1,3-dimethyloctyl, 4-methyloctyl, 1,2,2,3-tetramethylbutyl, 1,3,3-trimethylbutyl, 1,2,3 -trimethylbutyl, 1,3-dimethylpentyl, 1,3-dimethylhexyl, 5-methyl-3-hexyl, 2-methyl-4-heptyl, 2,6-di Methyl-4-heptyl and 1-methyl-2-cyclopropylethyl.

Representative of halogen-substituted alkyl groups such as chloromethyl, dichloromethyl, trichloro Methyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- Difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl Base, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloro-1-methylbutyl, 2-chloro-1-methylbutyl, 1-chlorobutyl, 3,3- Dichloro-1-methylbutyl, 3-chloro-1-methylbutyl, 1-methyl-3-trifluoromethylbutyl, 3-methyl-1-trifluoromethylbutyl.

The definition of a tri(C ₁ -C ₈ )alkylfluorenyl group preferably represents the following groups: SiMe ₃ , SiMe ₂ Et, SiMe ₂ CHMe ₂ , SiMe ₂ CH ₂ CHMe ₂ , SiMe ₂ CH ₂ CMe ₃ , SiMe ₂ CMe ₃ , SiMe ₂ CH ₂ CH ₂ Me.

The definition of C ₂ -C ₁₆ -alkenyl includes the definition of the maximum range of alkenyl in the text. In particular, this definition includes the meaning of vinyl, n-, isopropenyl, n-, i-, second-, and tri-butenyl, and in each case all isomerized pentenyl, Alkenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecyl, hexadecenyl, 1 Methyl-1-propenyl, 1-ethyl-1-butenyl, 2,4-dimethyl-1-pentenyl, 2,4-dimethyl-2-pentenyl.

The definition of C ₂ -C ₁₆ -alkynyl includes the definition of the maximum range of alkynyl groups herein. In particular, this definition includes the meaning of ethynyl-n-, iso-propynyl, n-, i-, second-, tri-butynyl, and in each case all isomerized pentynyl, Alkynyl, heptynyl, octynyl, decynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecanyl.

The cycloalkyl group is defined to include a monocyclic saturated hydrocarbon group having 3 to 8 carbon ring atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

The aryl group is defined to include unsubstituted or substituted, aromatic, mono-, bi- or tricyclic, such as phenyl, naphthyl, anthryl, phenanthryl.

The heterocyclic ring system is defined to include unsubstituted or substituted unsaturated heterocyclic 5- to 7-membered rings containing up to 4 heteroatoms selected from N, O and S: for example 2-furyl, 3-furyl, 2- Thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 1-pyrazolyl, 1H-imidazole Benzyl-2-yl, 1H-imidazolyl-4-yl, 1H-imidazolyl-5-yl, 1H-imidazolyl-1-yl, 2- Azolyl, 4- Azolyl, 5- Azyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-iso Azolyl, 4-iso Azolyl, 5-iso Azyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl , 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl, 1H-1,2,4-triazol-1-yl, 4H-1,2,4-tri Zyrid-3-yl, 4H-1,2,4-triazol-4-yl, 1H-tetrazol-1-yl, 1H-tetrazol-5-yl, 2H-tetrazol-2-yl, 2H- Tetrazolium-5-yl, 1,2,4- Diazol-3-yl, 1,2,4- Diazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4- Diazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,3- Diazol-4-yl, 1,2,3- Diazol-5-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5- Azoxa-3-yl, 1,2,5-thiadiazol-3-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-anthracene Base, 4-嗒 Base, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyridyl Base, 1, 3, 5 - three -2-base, 1,2,4-three -3-yl, 1,2,4-three -5-base, 1,2,4-three -6-based.

The substituted group may optionally be mono- or poly-substituted, wherein in the case of multiple substitutions, the substituents may be the same or different. Thus, the definition of a dialkylamino group also includes an asymmetric alkyl-substituted amino group, such as a methylethylamine group.

The halogen-substituted group, such as a haloalkyl group, is mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms may be the same or different. Halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

However, the general or preferred group definitions or descriptions given above may be combined with each other if desired, i.e., include combinations of specific ranges and preferred ranges. It is suitable for end products and correspondingly, precursors and intermediates.

However, the definitions and explanations of the groups given above, in general or in the preferred range, may also be combined with each other if desired, i.e., include combinations of specific ranges and preferred ranges. Both are suitable for the end product and corresponding precursors and intermediates. In addition, individual definitions may not apply.

Preferably, the compounds of formula (I) wherein each of the groups has the above preferred definition are administered.

Particularly preferred are the compounds of formula (I) wherein each of these groups has the above-defined definition.

Very particularly preferred are the compounds of formula (I) wherein each of these groups has the above-defined best definition.

If appropriate, the compounds of the invention may exist in mixtures of different possible isomeric forms, in particular stereoisomers such as E and Z, threo and erythro, and optical isomers, and if desired and by mutual mutation Structure. The patent application ranges from both E and Z isomers, and threo and erythro, as well as optical isomers, any mixture of these isomers and possible tautomeric forms.

Where appropriate, the compounds of the invention may exist in one or more optical or palmomere forms, depending on the number of asymmetric centers in the compound. The invention therefore relates to all optical isomers and their racemic or non-racemic mixtures (the term "non-racemic" refers to mixtures of different ratios of mirror image isomers) and all ratios. A mixture of possible stereoisomers. The diastereomers and/or optical isomers can be separated according to methods known per se to those skilled in the art.

If appropriate, depending on the number of double bonds in the compound, the compounds of the invention may also be Or multiple geometric isomer forms exist. The invention is therefore intended to be equivalent to all geometric isomers and all possible mixtures of all ratios. Geometric isomers can be separated according to conventional methods known to those of ordinary skill in the art.

If appropriate, depending on the relative position of the substituent (cis/trans), the compounds of the invention may One or more geometric isomer forms are present. The invention is therefore directed to all possible cis/trans mixtures of all geometric cis/trans isomers and all ratios. The cis/trans isomers can be separated according to a general method known to those skilled in the art.

Method and description of the intermediate

When the carbonyl halide or acid of formula (II) is combined with the amine of formula (III-a), if necessary in the presence of a coupling agent, optionally in the presence of an acid binder and, if desired, diluted When reacted in the presence of a reagent, a carboxamide of the formula (Ia) is obtained, wherein the T system represents oxygen [method (a)]:

Formula (II) provides a general definition of the carbonyl halide or acid required as a starting material for carrying out the process (a) according to the invention.

In the formula (II), Ar is generally and preferably has the meanings mentioned in the groups which have been described in connection with the description of the compounds of the formula (I). The Z series represents a halogen, a cyano group, a hydroxyl group or a reactive hydroxyl group, preferably a fluorine, chlorine or a hydroxyl group, particularly preferably a chlorine or a hydroxyl group.

A reactive hydroxyl group shall mean a hydroxyl group that forms an ester with an adjacent carbonyl group. Spontaneously reacts with amines. Common active esters include p-nitrophenyl, pentafluorophenyl, amber sulphite or phosphorous anhydride.

The carbonyl halide or acid of formula (II) can be prepared from commercially available starting materials using known procedures (see RC Larock Comprehensive organic transformations , 1989 , VCH publishers).

Formula (III-a) provides the amine required as a starting material for carrying out the process (a) according to the invention General definition.

In the formula (III-a), Q, X, m, R ¹ , R ² , R ³ and R ⁴ are generally, preferably, particularly preferably, very particularly preferably having such a formula ( I) Compounds indicate the meanings mentioned in the relevant groups.

When the carboxamide and the vulcanizing agent of the formula (Ia) are reacted as needed in the presence of a diluent, and if suitably reacted in the presence of a catalytic amount or a chemical amount of an acid binder, the sulfur of the formula (Ib) is obtained. Carbocaramine, wherein the T system represents sulfur [method (b)]:

The compound of the formula (III-a) used as a starting material is a compound of the formula (III-b) and a compound of the formula (V) or a compound of the formula (V) in the presence of a catalyst, if necessary Prepared by the reaction in the presence of an acid binder and/or in the presence of a diluent. An additional step may be required to obtain the free amine (Q is equal to H), for example, a suitable acid treatment or a metal-catalyzed hydrogenolysis [method (c)]:

Formula (III-b) provides the bromine required as a starting material for carrying out the process (c) according to the invention A general definition of a compound.

In the formula (III-b), X, m, R ¹ , R ² , R ³ and R ⁴ are generally, preferably, particularly preferably, very particularly preferably having these and the formula (I) The compounds illustrate the meanings mentioned in the relevant groups.

In the formula (V), Q is generally, preferably, particularly preferably, very particularly preferably having the meanings mentioned in the groups relating to the description of the compound of the formula (I), and the Y system represents Hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyloxy, phenoxy, benzyloxy.

The compound of the formula (III-b) used as a starting material is prepared by cyclizing a compound of the formula (VV) in the presence of a vehicle, a brominating agent and in the presence of a diluent (adjusted Bailey, WF) Tetrahedron letters , 1999, 40, 6899) [method (d)]:

Formula (VV) provides the iodination required as a starting material for carrying out the process (d) according to the invention The general definition of things.

In formula (VV), X, m, R ¹ , R ² , R ³ and R ⁴ are generally, preferably, particularly preferably, very particularly preferably having such compounds as described above with formula (I) The meaning mentioned in the relevant group.

The compound (VV) is commercially available or can be produced according to known methods (Bailey, WF Tetrahedron letters , 1999, 40, 6899).

a compound of the formula (III-b), in particular when R ¹ and R ² represent a C ₁ -C ₁₆ -alkoxy group, by reacting a compound of the formula (VI) with a compound of the formula (VII) in the presence of a base And prepared by the reaction in the presence of a diluent [Method (e)]:

Formula (VI) provides the iodination required as a starting material for carrying out the process (e) according to the invention The general definition of things.

In formula (VI), X and m are generally, preferably, particularly preferably, very particularly There are such meanings as those mentioned in the groups relating to the description of the compounds of the formula (I).

In the formula (VII), R ¹ , R ² , R ³ and R ⁴ are generally, preferably, particularly preferably, very particularly preferably having such groups which have been described in connection with the compounds of the formula (I) The meaning mentioned in the article.

Compounds of formula (VI) and compounds of formula (VII) are commercially available.

Alternatively, a compound of formula (III-c), that is, a compound of formula (III-a) wherein Q is a hydrogen, is derived from a compound of formula (III-d) and a source of azide, optionally in the presence of an activator Prepared by reacting as needed in the presence of an acid binder (Method f):

An additional step may be required to release the amine in its unprotected form, for example Suitable acid treatment or metal catalyzed hydrogenolysis.

Formula (III-d) provides the carboxylic acid required as a starting material for carrying out the process (f) according to the invention General definition.

In the formula (III-d), X, m, R ¹ , R ² , R ³ and R ⁴ are generally, preferably, particularly preferably, very particularly preferably having these and the formula (I) The compounds illustrate the meanings mentioned in the relevant groups.

The compound of the formula (III-d) is oxidized by a compound of the formula (III-e) in the presence of a diluent, by using a conventional process known in the literature (RC Larock Comprehensive organic transformations , 1989 , VCH publishers). Preparation (method g):

Formula (III-e) provides the aldehyde required as a starting material for carrying out the process (g) according to the invention A generic definition of a class.

In the formula (III-e), X, m, R ¹ , R ² , R ³ and R ⁴ are generally, preferably, particularly preferably, very particularly preferably having these and the formula (I) The compounds illustrate the meanings mentioned in the relevant groups.

The compound of formula (III-a) used as a starting material is prepared by cyclizing a compound of formula (VV) in the presence of a vehicle DMF and in the presence of a diluent (adjusted Bailey, WF Tetrahedron letters , 1999, 40, 6899) [method (h)]:

Suitable diluents for carrying out the processes (a), (b), (c), (d), (e), (f), (g) and (h) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decahydronaphthalene; Hydrocarbons such as chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether Methyl third amyl ether, two Alkane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Nitriles such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; guanamines such as N,N-dimethylformamide, N,N-dimethylacetamide, N- Methylformamide, N-methylpyrrolidone or tridecylamine hexamethylphosphate; a mixture with water or pure water.

Suitable acid binders for carrying out the processes (a), (b), (c), (d), (e), (f), (g) and (h) according to the invention may be customary The inorganic or organic base of the reaction. Preferably, an alkaline earth metal, an alkali metal hydride, an alkali metal hydroxide or an alkali metal alkane such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, butanol or other hydroxide is used. Ammonium, alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate, cesium carbonate, alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate and tertiary amines such as trimethylamine , triethylamine, diisopropylethylamine, tributylamine, N , N -dimethylaniline, pyridine, N -methylpiperidine, N , N -dimethylaminopyrrolidine, 1,4- Diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0] Eleven-7-ene (DBU).

When X ³ represents a hydroxy group, if appropriate, the process (a) according to the invention is carried out in the presence of a suitable coupling agent. Suitable coupling agents are all customary carbonyl activators. These preferably include N-[3-(dimethylamino)propyl]-N ' -ethyl-carbodiimide-hydrochloride, N,N ' -di-second-butylcarbodiimide Amine, N,N ' -dicyclohexylcarbodiimide, N,N ' -diisopropylcarbodiimide, 1-(3-(dimethylamino)propyl)-3-ethylcarb Diimine methyl iodide, 2-bromo-3-ethyl-4-methyltetrafluoroboric acid thiazolium salt, N,N-bis[2- side oxygen-3- Pyrazinyl]phosphonium diamine chloride, chlorotripyrrolidinium hexafluorophosphate, bromotripyrrolidinium hexafluorophosphate, O-(1H-benzotriazol-1-yloxy)anthracene Amino group) bismuth hexafluorophosphate, O-(1H-benzotriazol-1-yl)-N,N,N ' ,N ' -tetramethylhexafluorophosphate , O-(1H-benzotriazol-1-yl)-N,N,N ' ,N ' -bis(tetramethyl)hexafluorophosphate , O-(1H-benzotriazol-1-yl)-N,N,N ' ,N ' -bis(tetramethyl)tetrafluoroboric acid ,N,N,N ' ,N ' -bis(tetramethyl)chlorotetrafluoroboric acid , O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethylhexafluorophosphate And 1-hydroxybenzotriazole. These reagents can be used separately and in combination.

When carrying out the process (a) according to the invention, the reaction temperature can be in a relatively wide range Variety. In general, the process is carried out at a temperature of from 0 ° C to 150 ° C, preferably from 20 ° C to 110 ° C.

The preparation of the compound of the formula (I-a) by carrying out the process (a) according to the invention, generally per mole The carbonyl halide or acid of (II) is used in an amount of from 0.2 to 5 mol, preferably 0.5 to 2 mol, of the amine of the formula (III-a). Subsequent processing is carried out in a conventional manner.

The preparation of the compound of the formula (I-b) by carrying out the process (b) according to the invention can be carried out according to the method (a) It is prepared to prepare the starting decylamine derivative of the formula (I-a).

Suitable vulcanizing agents for carrying out the process (b) according to the invention may be sulfur (S), hydrogen sulfide (H ₂ S), sodium sulfide (Na ₂ S), sodium hydrosulfide (NaHS) or boron trisulfide (B). ₂ S ₃ ), bis(diethylaluminum) sulfide ((AlEt ₂ ) ₂ S), ammonium sulfide ((NH ₄ ) ₂ S), phosphorus pentasulfide (P ₂ S ₅ ), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphorane 2,4-disulfide) or a polymer-carrying vulcanizing agent, for example J. Chem. Soc., described in Perkin 1 2001 , 358.

Process (c) is carried out in the presence of a catalyst, optionally in the presence of an acid binder, in the presence of a diluent, and then with a suitable acid. Suitable acids for this purpose are from the common Brukers acid (Br Nsted acid), such as HCl, H ₂ SO ₄ , KHSO ₄ , AcOH, trifluoroacetic acid, p-toluenesulfonic acid, camphorsulfonic acid, triethanolamine-HCl, pyridine HCl.

Suitable catalysts for carrying out process (c) according to the invention may be selected from metal salts or Paste. Suitable metal derivatives for this purpose are based on palladium or copper. Suitable metal salts or complexes for this purpose are palladium chloride, palladium acetate, ruthenium (triphenylphosphine) palladium, bis(triphenylphosphine)palladium dichloride or 1,1'-bis ( Diphenylphosphino)ferrocene palladium(II) chloride, copper iodide, copper bromide, copper thiophenecarboxylate, copper trifluoromethanesulfonate, copper (I) oxide.

By separately adding a palladium salt and a complexing agent or a salt, such as a phosphine, for example, three Ethylphosphine, tert-butylphosphine, tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl, 2-(di-t-butylphosphine)biphenyl, 2-(dicyclohexylphosphine)-2' -(N,N-dimethylamino)-biphenyl, triphenylphosphine, 叁-(o-tolyl)phosphine, sodium 3-(diphenylphosphino)benzosulfonate, guanidine-2- (methoxyphenyl)phosphine, 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl, 1,4-bis-(diphenylphosphino)butane, 1,2- Bis-(diphenylphosphine)butane, 1,4-bis-(dicyclohexylphosphine)butane, 1,2-bis-(dicyclohexylphosphino)ethane, 2-(dicyclohexylphosphine)- 2'-(N,N-Dimethylamino)-biphenyl, bis(diphenylphosphino)ferrocene, ruthenium-(2,4-t-butylphenyl)-phosphite, R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine, (S)-(+)-1-[(R) )-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocene Ethyl dicyclohexylphosphine, (S)-(+)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine or 1,3 - Bis(2,4,6-trimethylphenyl)pyridinium chloride, it is also possible to produce a palladium complex in the reaction mixture.

By the separate addition of a copper salt and a complexing agent or salt, such as a diamine, for example, in the reaction Cyclohexyl 1,2-diamine, N,N'-dimethylethylidene diamine, cyclohexyl N,N'-dimethylamine may also produce a copper complex in the reaction mixture.

By "Metal Catalysts for Organic" by Strem Chemicals, for example It is also advantageous to select a suitable catalyst and/or complexing agent from the commercially available catalog of Synthesis or "Phosphorous Ligands and Compounds" of Strem Chemicals.

When carrying out the process (c) according to the invention, the reaction temperature can be in a relatively wide range Variety. In general, the process is carried out at a temperature of from 0 ° C to 150 ° C, preferably from 20 ° C to 110 ° C.

The preparation of the compound of the formula (III-a) by carrying out the process (c) according to the invention, generally per mole The bromide of the formula (III-b) is used in an amount of from 0.2 to 5 mol, preferably 0.5 to 2 mol, of the compound of the formula (IV). Subsequent processing is carried out in a conventional manner.

Suitable mediators for carrying out the processes (d), (e) and (h) according to the invention may be alkyl groups Lithium or alkyl magnesium reagents such as n-butyllithium, dibutyllithium, tert-butyllithium, methylmagnesium chloride, ethylmagnesium chloride or isopropylmagnesium chloride.

Suitable brominating agents for carrying out the process (d) according to the invention may be selected from 1,2-dibromoethane Alkane, bromine or N-bromosuccinimide.

If appropriate, the process (f) according to the invention is carried out in the presence of a suitable coupling agent. Suitable coupling agents are all customary carbonyl activators.

When carrying out the processes (d), (e) and (h) according to the invention, the reaction temperature can be quite extensive The scope of the change. In general, the process is carried out at a temperature of from -100 ° C to 0 ° C, preferably from -78 ° C to -45 ° C.

Methods (a), (b), (c), (d), (e), (f), (g) and (h) are generally at atmospheric pressure get on. However, it is also possible to operate under elevated or reduced pressure - typically between 0.1 and 100 bar.

Composition/formulation

The invention further relates to microorganisms for controlling undesired, in particular unwanted A crop protection composition of fungi and bacteria comprising an effective and non-phytotoxic amount of the active ingredient of the present invention. These are preferably fungicidal compositions comprising agriculturally suitable adjuvants, solvents, carriers, surfactants or extenders.

In the context of the present invention, "control of harmful microorganisms" means compared to untreated The fungicidal efficacy measured by plants reduces the infection of harmful microorganisms, preferably by 25-50% compared to untreated plants (100%), and more preferably compared to untreated plants ( 100%), 40-79% reduction; very well, overall inhibition of harmful microbial infections (70-100% reduction). The control can be therapeutic, i.e., for treating infected plants, or protective, for protecting uninfected plants.

"Effective but non-phytotoxic amount" means that the amount of the composition of the present invention is sufficient A satisfactory way to control fungal diseases of plants or to completely eradicate fungal diseases, and at the same time, it does not cause significant phytotoxic symptoms. In general, this rate of application can vary over a wide range. It is determined by several factors, for example, according to the fungi, plants, weather conditions and ingredients of the compositions of the invention to be controlled.

Suitable organic solvents include all polar and non-polar solvents commonly used for formulation purposes. Preferably, the solvent is selected from the group consisting of ketones such as methyl isobutyl ketone and cyclohexanone, guanamines such as dimethylformamide and decylamine alkanoates such as N,N-dimethylhydrazine. Amines and N,N-dimethyloctylamine, further cyclic solvents such as N-methyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone, N-octyl - caprolactam, N- dodecyl - caprolactam and butyrolactone, furthermore strongly polar solvents such as dimethyl sulfoxide and aromatic hydrocarbons, such as xylene, Solvesso ^TM, a mineral oil, e.g. White oil, petroleum, alkyl benzene and spindle oil, and esters such as propylene glycol monomethyl ether acetate, dibutyl adipate, hexyl acetate, heptyl acetate, tri-n-butyl citrate and Di-n-butyl phthalate, and alkanols such as benzyl alcohol and 1-methoxy-2-propanol.

According to the invention, the carrier is a natural or synthetic organic or inorganic substance, The active ingredients are mixed or combined for easier application, especially for application to plants or plant parts or seeds. The carrier, which may be solid or liquid, is generally inert and should be suitable for agricultural use.

Solid or liquid carriers which may be used include, for example, ammonium salts and natural stone dust, for example High territories, clay, talc, chalk, quartz, magnesium-aluminum sepiolite, montmorillonite or diatomaceous earth, and synthetic stone dust, such as fine powdered bismuth, aluminum sulphate and natural or synthetic bismuth, resin, Waxes, solid fertilizers, water, alcohols (especially butanol), organic solvents, mineral oils and vegetable oils and their derivatives. Mixtures of such carriers can likewise be used.

Suitable solid fillers and carriers include inorganic particles, for example with 0.005 to 20 μm, preferably 0.02 to 10 μm average particle size of carbonate, citrate, sulfate and oxide, such as ammonium sulfate, ammonium phosphate, urea, calcium carbonate, calcium sulfate, magnesium sulfate, magnesium oxide, Alumina, cerium oxide, so-called fine granules, cerium, natural or synthetic ceric acid salts, and aluminosilicates and plant products such as flour, wood powder/wood chips and cellulose powder.

Solid carriers useful for granules include, for example, crushed and finely divided natural ores, For example, calcite, marble, pumice, sepiolite, dolomite, and synthetic particles of inorganic and organic coarse powders, and particles of organic matter such as wood chips, coconut shells, corn cobs, and tobacco stems.

Liquefied gas extenders or carriers that can be used are such standard temperatures and standards A liquid of a gas under pressure, such as an aerosol propellant, such as a halocarbon, and butane, propane, nitrogen, and carbon dioxide.

In the formulation, it is possible to use tackifiers such as carboxymethylcellulose and powders, Natural and synthetic polymers in the form of granules or lattices, such as acacia, polyvinyl alcohol, polyvinyl acetate, or other natural phospholipids such as cephalin and lecithin, and synthetic phospholipids. Other additives may be mineral oils and vegetable oils.

If the extender used is water, it may also be used, for example, as an organic solvent. Auxiliary solvent. The liquid solvents that can be used are basically: aromatic systems such as xylene, toluene or alkane. a naphthalene, a chlorinated aromatic compound or a chlorinated aliphatic hydrocarbon such as chlorobenzene, vinyl chloride or methylene chloride, a fat hydrocarbon such as cyclohexane or paraffin, such as mineral oil fraction, mineral oil and vegetable oil, alcohol For example, butanol or glycerol and its ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl amide碸 and water.

Suitable interfacial active substances (adjuvants, emulsifiers, dispersants, protective colloids, Wetting agents and adhesives) include all common ionic and nonionic materials such as ethoxylated nonylphenols, polyglycol ethers of linear or branched alcohols, alkylphenols with ethylene oxide and/or propylene oxide Reaction product, reaction product of fatty acid amine with ethylene oxide and/or propylene oxide, further fatty acid ester, alkyl sulfonate, alkyl sulfate, alkyl ether sulfate, alkyl ether phosphate, Aryl sulfate, ethoxylated aralkyl phenols, such as tristyryl phenol ethoxylate, ethoxylated and propoxylated aralkyl phenols, such as sulfates or aryl phenols - Ethoxide and propoxide. Further examples are natural and synthetic water-soluble polymers such as lignin sulfate, gelatin, gum arabic, phospholipids, starch, hydrophobically modified starches and cellulose derivatives, in particular cellulose esters and cellulose ethers, Polyvinyl alcohol, polyvinyl acetate, polyvinylpyrrolidone, polyacrylic acid, polymethacrylic acid and a copolymer of methacrylic acid and methyl propyl acid ester, and further neutralized by alkali metal hydroxide A copolymer of methacrylic acid and methyl propyl ester and a condensation product of a substituted naphthalene sulfonate with formaldehyde, if desired. If one of the active ingredients and/or one of the inert carriers is insoluble in water and when applied in water, a surfactant is required. The proportion of surfactant is between 5 and 40 percent by weight of the composition of the invention.

Dyeing agents such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue can be used. And inorganic dyes such as alizarin dyes, diazo dyes and metal phthalocyanine dyes, and salts of micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Antifoaming agents which may be present in the formulation include, for example, hydrazine emulsions, long chain alcohols, Fatty acids and their salts as well as fluoroorganic substances and mixtures thereof.

Examples of thickeners are polysaccharides such as sinica or veegum, Citrate, such as attapulgite, strontium, and fine argon.

If appropriate, other components may be present, such as protective colloids, Agents, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, chelating agents, and complexing agents. In general, the active ingredient can be combined with any solid or liquid additive commonly used for formulation purposes.

The active ingredient or composition of the present invention, in accordance with its particular physical and/or chemical Nature, may be used in the form of its formulation, or from the form in which it is prepared, such as aerosols, capsule suspensions, concentrated cold sprays, concentrated hot aerosols, encapsulated granules, powdered granules, seed treatment water Suspension, ready-to-use solution, powder, emulsion, oil-in-water emulsion, water-in-oil emulsion, large granule, microparticle, oil dispersible powder, oil suspension, oil suspension, gas (under pressure), gas generating agent, Foaming agents, pastes, seed coatings, suspensions, suspoemulsions, solutions, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or lozenges, water-soluble and water-dispersible for seed treatment Powders, wettable powders, natural and synthetic materials infused with active ingredients, as well as microencapsulated in polymers and coated materials for seeds, and ULV cold fog and hot mist formulations.

The compositions of the present invention include not only ready-to-use and suitable device applications Formulations for plants or seeds, including commercial concentrates that must be diluted with water prior to use. Conventional application is, for example, a spray liquid produced by dilution in water and subsequent spraying, application after dilution with oil, and direct application of soil without dilution, seed treatment or granules.

The compositions and formulations of the present invention generally comprise from 0.05 to 99% by weight, From 0.01 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 10 to 70% by weight. For specific applications, such as wood protection and derived wood products, the compositions and formulations of the present invention typically comprise from 0.0001 to 95% by weight, preferably from 0.001 to 60% by weight, of active ingredient.

In the form of application prepared from commercially available formulations, the active ingredient may be present in a wide range. The scope of the pan changes. The concentration of the active ingredient in the application form is generally from 0.000001 to 95% by weight, preferably from 0.0001 to 2% by weight.

The formulations mentioned may be prepared by methods known per se, for example, And at least one conventional extender, solvent or diluent, adjuvant, emulsifier, dispersant and / or binding agent or fixative, wetting agent, water repellent, if appropriate drier and UV stabilizer, And if appropriate, dyes and pigments, defoamers, preservatives, inorganic and organic thickeners, adhesives, gibberellin, and additional processing adjuvants and water. Further processing steps are necessary, such as wet milling, dry milling, and granulation, depending on the type of formulation desired to be prepared.

The active ingredients of the present invention, or their (commercial) formulations, and by these formulations The form of use prepared may be present with a mixture of other (known) active ingredients.

The invention treats plants and plant parts directly with active ingredients or compositions Or by conventional treatment methods, such as dipping, spraying, spraying, irrigating, evaporating, dusting, atomizing, spreading, foaming, coating, spreading, watering (drenching) , drip irrigation in its surroundings, habitat or storage space, and in the case of the reproduction of matter, especially in the case of seeds, also by dry seed treatment, humidification seed treatment, slurry treatment, covering, coating one or more coatings Wait a minute. Alternatively, the active ingredient can be administered by ultra low volume methods or by injecting the active ingredient preparation or the active ingredient itself into the soil.

Plant/crop protection

The active ingredients or compositions of the present invention have potent microbicidal activity and can be used in crop protection and material protection for undesirable microorganisms such as fungi and bacteria.

The invention also relates to a method of controlling unwanted microorganisms, characterized in that the active ingredient of the invention is applied to phytopathogenic fungi, phytopathogenic bacteria and/or their habitat.

Fungicides can be used for crop protection for the control of phytopathogenic fungi. It is characterized by its superior efficacy against a broad spectrum of phytopathogenic fungi, including soil-borne pathogens, especially the following members: Plasmodiophoromycetes , Peronosporomycetes [ Oomycetes ] , Chytridiomycota (Chytridiomycetes), Zygomycetes (Zygomycetes), aurantiacus (ascomycetes), Basidiomycetes (Basidiomycetes) and incomplete bacteria (, Deuteromycetes) [synonym: fungi Deuteromycetes (fungi imperfecti)]. Certain fungicides are systemically active and can be used for plant protection as a leaf, seed dressing or soil fungicide. Furthermore, it is suitable for solving fungi in which wood or plant roots are infected.

Bactericides can be used for prevention and treatment of crop protection Pseudomonas (Pseudomonadaceae), Rhizobium (Rhizobiaceae), Enterobacteriaceae (Enterobacteriaceae), Corynebacterium (Corgnebacteriaceae) and Streptomyces (Streptomycetaceae).

Non-limiting examples of fungal disease pathogens which may be treated according to the invention include: diseases caused by powdery mildew, such as Blumeria , such as Blumeria graminis ; Podosphaera ), such as Podosphaera leucotricha ; Sphaerotheca , such as Sphaerotheca fuliginea ; Uncinula , such as the powdery mildew ( Uncinula) Necator ); a disease caused by a rust pathogen, such as Gymnosporangium , such as Gymnosporangium sabinae ; Hemileia , such as Hemileia vastatrix ; genus (Phakopsora), for example, P. pachyrhizi (Phakopsora pachyrhizi) and locust hill horse layer rust (Phakopsora meibomiae); Puccinia (Puccinia), for example, Puccinia rust (Puccinia recondite), leaf rust ( P.triticina), Puccinia graminis (P.graminis), stripe rust pathogen (P.striiformis); Micromonospora genus rust (Uromyces), such as a wart top Uromyces (Urom Yces appendiculatus ); a disease caused by the pathogen of the oomycete , such as Albugo , such as Algubo candida ; for example, Bremia , such as Lactococcus dysenteriae ( Bremia lactucae ); Peronospora , such as Peronospora pisi or P. brassica ; Phytophthora , such as Phytophthora infestans ; Plasmopara , such as Plasmopara viticola ; Pseudoperonospora , such as Pseudoperonospora humuli or Pseudoperonospora cubensis ; Pythium, for example Pythium ultimum ; leaf spot and leaf blight caused by, for example, Alternaria , such as Alternaria solani ; Cercospora For example, Cercospora beticola ; Cladiosporum , such as C. glabrata ( Cladiosporium cucumeri) Num ); Cochliobolus , such as Cochliobolus sativus (conidial form: Drechslera , synonym: Helminthosporium ); rice rotation bacteria spore cavity (Cochliobolus miyabeanus); genus Colletotrichum (Colletotrichum), e.g. kidney bean anthracnose (Colletotrichum lindemuthanium); the genus leaf spot (Cycloconium), for example olive peacock bacteria (Cycloconium oleaginum); seat shell between genera (Diaporthe), For example, Diaporthe citri ; Elsinoe , such as Elsinoe fawcettii ; Gloeosporium , such as Gloeosporium laeticolor ; Glomerella , such as Glomerella cingulata ; Guignardia , such as Guignardia bidwelli ; Leptosphaeria , such as roots Leptosphaeria maculans , Leptosphaeria nodorum ; Magnaporthe , such as Magnaporthe oryzae (Magn) Aporthe grisea); Microdochium , such as Microdochium nivale ; Mycosphaerella , such as Mycosphaerella graminicola , M. arachidicola And M. fijiensis ; Phaeosphaeria , such as Phaeosphaeria nodorum ; Pyrenophora , such as Pyrenophora teres , wheat yellow spot Pyrenophora tritici repentis ; Ramularia , such as Ramularia collo-cygni , Ramularia areola ; Rhynchosporium , such as rye Rhynchosporium secalis ; Septoria , such as Septoria apii , Septoria lycopersii , Typhula , such as Rhizoctonia solani Typhula incarnate ); Venturia , such as Venturia inaequalis ; root and stem diseases caused by the following, such as Cortici Um ), for example, Corticium graminearum ; Fusarium , such as Fusarium oxysporum ; Gaeumannomyces , such as Gaeumannomyces graminis Rhizoctonia , such as Rhizoctonia solani ; for example, a mycobacterial disease caused by Sarocladium oryzae ; for example, caused by Sclerotium oryzae Sclerotinia sclerotiorum; Tapesia , such as Tapesia acuformis ; Thielaviopsis , such as Thielaviopsis basicola ; ear caused by And inflorescences (including corn cob) diseases, such as Alternaria , such as Alternaria spp .; Aspergillus , such as Aspergillus flavus ; Cladosporium ( Cladosporium), branches and shoots e.g. cinerea (Cladosporium cladosporioides); genus Claviceps (Claviceps), e.g. violet ergot (Claviceps purpurea); Fusarium (Fusarium), e.g. Color Fusarium (Fusarium culmorum); the genus Fusarium (Gibberella), e.g. zearalenone (Gibberella zeae); Grignard Geotrichum (Monographella), snow mold, for example a Grignard mold (Monographella nivalis); the genus Septoria (Septoria ), for example, Septoria nodorum ; diseases caused by smut fungi, such as Sphacelotheca , such as Sphacelotheca reiliana ; Tilletia ), such as Tilletia caries , T. controversa ; Urocystis , such as Urocystis occulta ; Ustilago ), such as Ustilago nuda , U. nuda tritici ; fruit rot caused by the following, such as Aspergillus , such as Aspergillus flavus ; genus Botrytis (Botrytis), for example, Botrytis cinerea (Botrytis cinerea); Penicillium (Penicillium), for example, extended (Penicillium expansum), and Penicillium purpurogenum (P.purpurogenum) Penicillium; Sclerotinia Sclerotinia , such as Sclerotinia sclerotiorum ; Verticilium , such as Verticilium alboatrum ; seed and soil rot, mildew, dry disease, rot and damping-off diseases such as Altemaria species (of Alternaria), for example, cruciferous Alternaria (Alternaria brassicicola) caused; genus Aphanomyces (Aphanomyces), for example, Aphanomyces root rot (Aphanomyces Caused by euteiches ; genus Ascochyta , caused by, for example, Ascochyta lentis ; Aspergillus , caused by, for example, Aspergillus flavus ; Cladosporium ( Cladosporium ), caused by, for example, Cladosporium herbarum ; Cochliobolus , for example, from Cochliobolus sativus (conidial form: Drechslera ) , caused by Helminthosporium ; Colletotrichum , caused by, for example, Colletotrichum coccodes ; Fusarium ), caused by, for example, Fusarium culmorum ; Gibberella , caused by, for example, Gibberella zeae ; Macrophomina , for example, by Coccidioides ( Macrophominaphaseolina) caused; Grignard Geotrichum (Monographella), for example, snow mold Grignard mold (Monographella nivalis) caused; Penicillium (Penicillium), caused by, for example Penicillium expansum (Penicillium expansum); Phoma genus ( Phoma ), caused by, for example, Phoma lingam ; Phomopsis , caused by, for example, Phomopsis sojae ; Phytophthora , for example by Caused by Phytophthora cactorum ; Pyrenophora , caused by, for example, Pyrenophora graminea ; Pyricularia , caused by, for example, Pyricularia oryzae ; genus Pythium (Pythium), caused by, for example Pythium ultimum (Pythium ultimum); Rhizoctonia (Rhizoctonia), for example, Rhizoctonia solani (Rhizoctonia Caused by solani ; Rhizopus , caused by, for example, Rhizopus oryzae ; Sclerotium , caused by, for example, Sclerotium rolfsii ; Septoria , caused by, for example, Septoria nodorum ; Typhula , caused by, for example, Typhula incarnata ; Verticilium , for example by Dali Wheel Caused by Verticillium dahliae ; cancer, ticks and clusters caused by the following, such as Nectria , such as Nectria galligena ; caused by Blight , such as Monilinia , such as Monilinia laxa ; blister or leaflet caused by the following, such as Exobasidium , such as damage Exobasidium vexans ; Taphrina , such as Taphrina deformans ; woody plant degenerative diseases caused by: for example, Isca disease, such as Fusarium oxysporum Phaemoniell a clamydospora ) and ( Phaeoacremonium aleophilum ) and Fomitiporia mediterranea ; top blight, for example caused by Eutypa lata ; Ganoderma lucidum disease, such as Ganoderma boninense Caused by; Rigidoporus, for example caused by Rigidoporus lignosus ; flower and seed diseases caused by, for example, Botrytis , such as Botrytis Cinerea ); a plant tuber disease caused by, for example, Rhizoctonia , such as Rhizoctonia solani ; Helminthosporium , such as Helminthosporium Solani ); for example, caused by Plamodiophora , such as Plamodiophora brassicae ; diseases caused by bacterial pathogens, such as Xanthomonas , such as rice yellow Aeromonas varieties of rice (Xanthomonas campestris pv.Oryzae); Pseudomonas (Pseudomonas), e.g. cucumber P. syringae Pathogenic species ( Pseudomonas syringae pv . Lachrymans ); Erwinia , such as Erwinia amylovora .

It is preferably used for the control of the following soybean diseases: fungal diseases of leaves, stems, pods and seeds caused by: Streptomyces leaf spot ( atrans tenuissima ), anthracnose ( Colletotrichum gloeosporoides dematium var. truncatum ), brown spot ( Sydney glycines, Sepia glycines , Cercospora leaf spot and withered ( Cycospora kikuchii ), Fusarium oxysporum ( Chane fungus ( choanephora infundibulifera trispora ), Phytophthora leaf spot ( dactuliophora glycines ), downy mildew ( Peronospora manshurica ), Germany Fusarium wilt ( Dreckslera glycini ), frog eye leaf spot ( Cercospora sojina ), small light cavity leaf spot ( Leptosphaerulina trifolii ), Leaf spot mildew ( Phlyllosticta sojaecola ), pod blight and stem blight ( Phomopsis sojae ), powdery mildew ( Microsphaera diffusa ), Oxytropis leaf spot Beans Pyrenochaeta (Pyrenochaeta glycines)), Rhizoctonia leaf and ground network blight (Rhizoctonia solani (Rhizoctonia solani)), rust (P. pachyrhizi (Phakopsora pachyrhizi) and mountain horse locust pachyrhizi ( Phakopsora meibomiae )), rickets ( Sphaceloma glycines ), Bacterial leaf blight ( Stemphylium botryosum ), target spot disease ( Corynespora cassiicola ).

Fungal diseases of the roots and stems caused by: for example, black root rot ( Calonectria crotalariae ), bud rot ( Macrophomina phaseolina ), Fusarium wilt, root rot and Pod and neck rot ( Fusarium oxysporum , Fusarium orthoceras , Fusarium semitectum , Fusarium equiseti , mycoleptodiscus root rot (Eichhornia crassipes) Mycoleptodiscus terrestris ), Neocosmopspora vasinfecta , pod and stem wilt ( Diporthe phaseolorum ), stem canker ( Diaporthe phaseolorum var .caulivora), Phytophthora rot (Phytophthora soybean (Phytophthora megasperma), brown stem rot (Monilinia fructicola soybean stem (Phialophora gregata), Pythium rot of (Pythium (Pythium aphanidermatum), abnormal estrogen rot Pythium irregulare , Pythium debaryanum , Pythium myriotylum , Pythium ultimum , Rhizoctonia rot, Stem rot And sputum disease ( Rizoctonia solani ), sclerotial stem rot ( Sclerototinia sclerotiorum ), sclerotial chalk disease (Sclerotia sclerotium ( Sclerototinia rolfsii ), Rhizoctonia root rot ( Thielaviopsis basicola ).

The fungicidal composition of the invention can be used for therapeutic or protective/prophylactic control a pathogenic fungus. The invention therefore also relates to a therapeutic and protective method for controlling pathogenic fungi by using the active ingredient or composition of the invention, which is applied to the soil in which seeds, plants, plant parts, fruits or plants are grown.

In fact, the plant's good tolerance to the active ingredients at the concentrations required to control plant diseases allows it to be used to treat plant aerial parts, plant propagation material and seeds and soil.

All plants and plant parts can be treated according to the invention. By plant is meant all plants and flora, such as desired and unwanted wild plants, cultivars and plant products. Species (whether or not protected by plant variety rights or plant breeder rights). Cultivars and plant varieties can be obtained by conventional breeding and breeding methods, which can be performed by one or more, for example, using diploid, protoplast fusion, random and direct mutation, molecular or genetic markers, or by bioengineering and Genetic engineering methods to aid or supplement. By plant part is meant all plant parts and organs above and below the plant, such as buds, leaves, flowers and roots, such as leaves, thorns, stems, branches, flowers, fruiting bodies, fruits and seeds. And roots, tubers and underground stems. Harvested material and asexual and reproductive reproductive material, such as cuttings, tubers, underground stems, strips and seeds, also belong to plant parts.

The active ingredient of the present invention is advantageous in that it is completely tolerated by the plant. The warm-blooded animal toxicity and good environmental tolerance are suitable for protecting plants and plant organs for increasing yield and improving the quality of the harvest. It is preferably used as a crop protection composition. It is effective against general sensitive and resistant species and against all or some of the developmental stages.

Plant lines that can be treated in accordance with the present invention include the following major crop plants: corn, soybean, alfalfa, cotton, sunflower, mustard oil such as Brassica napus (eg, mustard, colza), turnip ( Brassis rapa ), mustard greens ( B.juncea ) (eg (field) mustard) and Ethiopian mustard ( Brassica carinata ), palm family ( Arecaceae sp (eg oil palm, coconut), rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet And sorghum, triticale, flax, nuts, grapes and vines and various fruits and vegetables from various plant types, such as Rosaceae sp . (eg, pome fruits such as apples and pears, and stone fruits such as apricots) , cherries, almonds, plums and peaches, and berries such as strawberries, raspberries, red currants and currants and gooseberries), Ribesioidae sp ., Juglandaceae sp . , Betulaceae sp ., Anacardiaceae sp ., Fagaceae sp ., Moraceae sp ., Oleaceae sp . (eg olive tree), kiwifruit Actinidaceae sp .) Lauraceae sp . (eg avocado, cinnamon, eucalyptus ), Musaceae sp . (eg banana and banana garden), Rubiaceae sp . (eg coffee), Camellia ( Theaceae) Sp .) (eg tea), sylvestris ( Sterculiceae sp .), Rutaceae sp . (eg lemon, orange, orange and grapefruit); Solanaceae s p. (eg tomato, potato, Pepper, pepper, eggplant, tobacco), Liliaceae sp ., Compositaesp . (eg lettuce, artichoke and chicory - including root chicory, endive or common chicory) , Umbelliferae sp . (eg carrot, celery, celery and celery), Cucurbitaceae sp . (eg cucumbers - including pickled cucumbers, pumpkins, watermelons, gourds and melons), onion ( Alliaceae sp .) (eg, amaranth , onion), Cruciferae sp . (eg, white cabbage, red cabbage, broccoli, white broccoli, spore cabbage, pakchoi, broccoli, white radish, horseradish, cress and cabbage), legumes (Leguminosae sp.) ( Such as peanuts, peas, lentils and beans - such as general beans and broad beans), Chenopodiaceae (Chenopodiaceae sp) (e.g. Switzerland beet, fodder beet, spinach, beetroot), Linaceae (Linaceae sp) (e.g. hemp), cannabis. Section (eg hashish), Malvaceae (Malvaceaesp) (such as okra, cocoa), poppy (Papaveraceae) (eg poppy), aspartame Branch (Asparagaceae) (eg asparagus) (Cannabeacea sp.); gardens and forests Useful plants and ornamentals, including grass, turf, grass and stevia ( Stevia rebaudiana ); and the genetically modified species of these plants in each case.

Seed treatment

The invention further includes a method of treating a seed.

The invention further relates to a seed treated by one of the methods described above. The seed of the present invention is used in a method for protecting seeds from harmful microorganisms. In these methods, seeds treated with at least one active ingredient of the invention are used.

The active ingredients or compositions of the invention are also suitable for use in treating seeds. Most of the crop damage caused by pests is caused by infection of the seeds during or after sowing and during or after germination of the plants. This phase is particularly important because the growing plants are particularly sensitive to their roots and shoots, and even a small amount of damage can cause plant death. Therefore, it is greatly advantageous to protect seeds and germinating plants by using appropriate compositions.

Controlling plant pathogenic fungi by treating the seeds of plants for a long time and The main body of continuous improvement. However, the processing of seeds has caused a series of problems that cannot always be resolved in a satisfactory manner. For example, it is desirable to develop methods for protecting seeds and germinating plants that are exempt or at least significantly reduce the deployment of additional crop protection compositions after sowing or after emergence of the plants. It is also desirable to optimize the amount of active ingredient used to provide the best possible protection of the seed and germinating plants from attack by phytopathogenic fungi, but the plants themselves are not harmed by the active ingredients used. In particular, the method of treating seeds should also take into account the original fungicidal properties of the genetically modified plants in order to achieve optimal protection of the seeds and germinating plants with minimal crop protection composition.

The invention therefore also relates to the protection of species by treating the seed with the composition of the invention The method of attacking germinated plants from phytopathogenic fungi. The invention is also directed to the use of the compositions of the invention for treating seeds for protecting seeds and germinating plants from phytopathogenic fungi. The invention further relates to seeds treated with the compositions of the invention for protection against phytopathogenic fungi.

The prevention and control of phytopathogenic fungi of plants after injury is mainly caused by The material protection composition is treated by treating the soil and the aerial parts of the plants. Due to concerns about the possible impact of crop protection compositions on the environment and human and animal health, it is desirable to minimize the amount of active ingredient disposed.

One of the advantages of the present invention is that the special components of the active ingredients and compositions of the present invention By performance, it is meant that treating the seed with these active ingredients or compositions not only protects the seed itself, it also blocks the phytopathogenic fungus after emergence of the plant. In this way, crops can be dispensed with at the time of sowing or shortly after sowing.

It is also considered to be advantageous if the active ingredient or composition of the invention is also used in particular The gene is transferred to a seed, wherein the plant grown from the seed can express a protein resistant to pests. By treating the seed with the active ingredient or composition of the invention, only protein expression, such as insecticidal proteins, can be prevented Treat specific pests. Surprisingly, another synergistic effect can be observed in this case, which can additionally increase the protective effect against pest attack.

The composition of the invention is suitable for use in protecting any agriculture, greenhouse, forest or horticulture and Seeds of various plants used in viticulture. In particular, it is a mites (such as wheat, barley, rye, triticale, sorghum / millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, beets (such as sugar beets and Seeds of fodder beet), peanuts, canola, poppy, olives, coconut, cocoa, sugar cane, tobacco, vegetables (eg tomatoes, cucumbers, onions and lettuce), turf and ornamental plants (see also below). Of particular importance are seed treatments of alfalfa (eg wheat, barley, rye, triticale and oats), corn and rice.

Gene transfer by treatment with the active ingredient or composition of the invention, as described below Seeds are especially important. This means that the plant seed contains at least one heterologous gene. Definitions and examples of suitable heterologous genes are as follows.

In the context of the present invention, the compositions of the present invention are applied alone or in a suitable formulation. Used for seeds. Preferably, the seed is treated in a state in which it is stable enough to cause no damage during processing. In general, seed treatment can be carried out at any time between harvesting and sowing. The seed line usually used has been isolated from the plant and removed from the cob, shell, stem, rind, hair, or pulp of the fruit. For example, seeds that have been harvested, cleaned, and dried to a moisture content of less than 15% by weight can be used. Alternatively, seeds that have been dried, such as water treated and then dried, may also be used.

In the treatment of seeds, it is generally necessary to pay attention to the composition of the invention applied to the seed. The amount and/or the amount of additional additives selected will not adversely affect the germination of the seed or be harmless to the resulting plant. This should be especially important when the active ingredient may have a phytotoxic effect at a particular rate of application.

The composition of the present invention can be applied directly, that is, does not include any other components and is not Dilution. In general, the composition is preferably applied to the seed in a suitable formulation. suitable Formulations and methods for the treatment of seeds are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/ 080675, WO 2002/028186.

The active ingredients usable in accordance with the invention can be converted into conventional seed dressings. A coating composition for solutions such as solutions, emulsions, suspensions, powders, foams, slurries or other seeds, and ULV formulations.

These formulations are added in a known manner by the addition of active ingredients and conventional ingredients. The agent is prepared, for example, as a conventional extender and a solvent or diluent, a dye, a wetting agent, a dispersing agent, an emulsifier, an antifoaming agent, a preservative, a second thickener, an adhesive, gibberellin, and water.

A dyeing agent which may be present in a seed dressing formulation which can be used in accordance with the invention is There are dyes used for these purposes. Water-soluble pigments or water-soluble dyes can be used. Examples include known dyes known as Rhodamin B, C.I. Pigment Red 112, and C.I. Solvent Red 1.

Useful wetting that can be present in a seed dressing formulation that can be used in accordance with the present invention The agent is any substance that enhances the degree of moisturization and is used in the formulation of active agrochemical ingredients. Preferably, an alkylnaphthalenesulfonate such as diisopropyl naphthalenesulfonate or diisobutyl ester is used.

Useful dispersions that may exist in seed dressing formulations that may be used in accordance with the present invention The agents and/or emulsifiers are all nonionic, anionic and cationic dispersing agents which are customary in the formulation of active agrochemical ingredients. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include (particularly) ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers and their phosphorylation or sulfated derivatives. Things. Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylates and arylsulfonate/formaldehyde condensates.

Seed dressing formulations that can be used in accordance with the present invention can be stored The antifoaming agent is a foam inhibiting substance which is conventionally used in the formulation of agrochemical active ingredients. Deuterium defoamers and magnesium stearate are preferably used.

Preservatives which may be present in the seed dressing formulations which may be used in accordance with the invention are All substances which can be used for agrochemical compositions for this purpose. Examples include dichlorophenol and benzyl alcohol hemiformal.

A second increase in the presence of a seed dressing formulation that can be used in accordance with the present invention Thickeners are all substances which can be used in agrochemical compositions for this purpose. Preferred examples include cellulose derivatives, acrylic acid derivatives, santillac gum, modified clay, and finely divided oxime.

Adhesives which may be present in the seed dressing formulations which may be used in accordance with the invention are All custom builders that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.

The amount of gibberellin that can be present in a seed dressing formulation that can be used in accordance with the present invention Preferably, it is gibberellin A1, A3 (= gibberellic acid), A4 and A7, of which gibberellic acid is particularly preferred. Gibberellin is known (cf. Wegler "Chemie der Ptlanzenschutz-und Schädlings bekämpfungsmittel" [Chemistry of the Crop Protection Compositions and Pesticides], vol. 2, Springer Verlag, 1970, p. 401-412).

Seed dressing formulations that can be used in accordance with the present invention can be used directly or first with water Diluted to treat a wide range of different seeds, including seeds of genetically transformed plants. In this case, additional synergies may occur due to interactions with the substances formed by the performance.

In the case of seed dressing formulations which can be used in accordance with the invention, or in the treatment of seeds from the preparations prepared therefrom by the addition of water, all of the mixing elements conventionally used in the accompanying species can be used. In particular, the seed dressing procedure places the seeds in a mixer, either directly or after dilution with water, adding a specific amount of the seed dressing product formulation, and mixing everything until the formulation is evenly distributed over On the seed. If appropriate, a drying step can be followed.

Mycotoxins

Further, the treatment of the present invention can reduce the mycotoxin content of the harvested material and the food and feed prepared therefrom. Mycotoxins include, in particular (but not exclusively) the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 - and HT2-toxin, fumonisine, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), white stiff Beauuvicin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids, and xanthotoxin (aflatoxins), which can be produced, for example, by the following fungi: Fusarium , such as F. acuminatum , F. asiaticum , F. avenaceum , gram F. crookwellense , F. culmorum , F. graminearum ( Gibberella zeae ), F. equithei , Fusarium oxysporum F.fujikoroi ), F.musarum , F. oxysporum , and then F. proliferatum , F. poae , F. pseudoidinearum , F. sambucinum , F. scirpi , F. semitectum , F. solani, F. sporotrichoides , F. langsethiae , F. subglutinans , three-line trowel bacteria (F.tricinctum), Fusarium Verticillium (F.verticillioides), etc., and the genus aspergillus, e.g. yellow aspergillus (A.flavus), parasitic aspergillus (A.parasiticus), aspergillus bee set (A.nomius ), A. ochraceus , A. clavatus , A. terreus , A. versicolor , Penicillium, such as Penicillium spp. ( P. verrucosum), bright green Penicillium (P.viridicatum), orange Penicillium (P.citrinum), Penicillium expansum (P.expansum), Penicillium rod (P.claviforme), Penicillium roqueforti (P.roqueforti) , ergot genus (Claviceps), such as purple ergot fungus (C.purpurea), ergot fungus (C. fusiformis), paspalum ergot fungus (C.paspali), Africa ergot fungus (C.afri Cana ), Stachybotrys and others.

Material protection

The active ingredients or compositions of the present invention can also be used for material protection to protect industrial materials against attack and destruction by unwanted microorganisms such as fungi and insects.

Furthermore, the compounds of the invention may be used as anti-fouling compositions, either alone or in combination with other active ingredients.

In the context of the present invention, industrial materials are understood to mean inanimate materials which have been prepared for industrial use. For example, industrial materials that can be protected from microbial changes or damage by the active ingredients of the present invention can be adhesives, gums, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and paper towels, lacquers and plastic articles. , cooling lubricants and other substances that can be infected or destroyed by microorganisms. Parts of production plants and buildings, such as cooling water circuits, cooling and heating systems, and ventilation and air conditioning components that can be compromised by microbial proliferation, can also be mentioned within the scope of materials that can be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, papers and boards, leather, wood, lacquers, cooling lubricants and heat transfer fluids, more preferably wood.

The active ingredient or composition of the present invention can prevent adverse effects such as spoilage, decay, discoloration, discoloration or mold.

In the case of wood treatment, the compounds/compositions of the invention may also be used to combat fungi that are readily grown on or in the wood. The term "wood" refers to all types of wood species, and all types of wood processing intended for use in construction, such as solid wood, high density wood, laminated wood and plywood. The method for treating wood according to the present invention is primarily continuous contact with one or more of the present hair-emitting compounds or compositions of the present invention; such items include, for example, direct coating, spraying, soaking, injecting, or any other suitable method.

In addition, the compounds of the present invention can be used to protect the subject matter in contact with sea water or salt water. In particular, hulls, screens, nets, buildings, breakwaters and communication components to avoid fouling.

The method of the present invention for controlling undesired fungi can also be used to protect stored articles. Storage Storage of articles should be understood to refer to natural substances of vegetable or animal origin or processed products thereof, and is desirable for their long-term protection. Plant-derived storage items, such as plants or plant parts such as stems, leaves, tubers, seeds, fruits, and mites, can be protected just after harvest or after drying, wetting, splitting, milling, pressing or baking. . The stored items may also include unprocessed wood such as construction timber, utility poles and fences, or finished products such as furniture. Storage items of animal origin are, for example, hides, leather, feathers and hair. The active ingredient of the present invention can prevent adverse effects such as spoilage, decay, discoloration, discoloration or mold.

Microorganisms that can degrade or alter industrial materials include, for example, bacteria, fungi, yeasts, algae, and mucous organisms. The active ingredient of the present invention are preferably used against based fungi, in particular molds, wood - and wood discoloration --destroying fungi (ascomycetes (Ascomycetes), Basidiomycetes (Basidiomycetes), incomplete fungi (, Deuteromycetes) and Zygomycetes (Zygomycetes) ), and against mucus organisms and algae. Examples include microorganisms of the following genera: Alternaria , such as Alternaria ( Alternaria tenuis ); Aspergillus , such as Aspergillus niger ; Chaetomium ), for example, Chaetomium globosum ; Coniophora , such as Coniophora puetana ; Lentinus , such as Lentinus tigrinus ; Penicillium For example, Penicillium glaucum ; Polyporus , such as Polyporus versicolor ; Aureobasidium , such as Aureobasidium pullulans ; (as Sclerophoma), e.g. pine leaves germs (Sclerophoma pityophila); Trichoderma (Trichoderma), for example, Trichoderma viride (Trichoderma viride); (. Ophiostoma spp) housing the nozzle genus Ceratocystis spp (. Ceratocystis spp), rot Humicola spp., Petriella spp., Trichurus spp.; Coriolus spp., Gloeoph Yllum spp.), Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp. , Paecilomyces spp, Mucor, genus (Escherichia), such as E. coli (Escherichia coli) (Paecilomyces spp. ) (Mucor spp.); Pseudomonas (of Pseudomonas), e.g. Pseudomonas aeruginosa (of Pseudomonas aeruginosa); Staphylococcus (Staphylococcus), such as Staphylococcus aureus (Staphylococcus aureus), Candida species (Candida spp) and Saccharomyces (Saccharomyces spp), such as Saccharomyces cerevisiae (Saccharomyces cerevisae).

Antifungal activity

In addition, the active ingredients of the present invention also have very good anti-fungal activity. It has a very broad-spectrum anti-fungal activity, especially against dermatophytes and yeasts, molds and biphasic fungi (eg anti-candida, such as C. albicans , Candida glabrata) C. glabrata )) and epidermophyton floccosum , genus Fusarium , such as A. niger and A. fumigatus , Trichophyton , such as hair mentagrophytes class (T.mentagrophytes), Bacillus Spp small (Microsporon), for example, the size of the spores dermatophytes (M.canis) and Audubon Ang (s) small spores rubrum (M.audouinii). The listed fungi are not intended to limit the scope of any of the covered molds, but are merely illustrative.

The active ingredients of the invention are therefore useful in both medical and non-medical applications.

Application rate and appropriate time

When the active ingredient of the present invention is used as a fungicide, the application rate can vary within a relatively wide range depending on the type of application. The application rate of the active ingredient of the present invention is: ̇ in the case of treating plant parts, such as leaves: from 0.1 to 10000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 10 to 800 g/ha, even Good land 50 to 300 g / ha (when When the application is carried out by sprinkling or dripping, the application rate can be even reduced, especially when using an inert substance such as rock wool or nacre.) The condition of the seed is treated: 2 to 200 g per 100 kg of seed, preferably 3 to 150 grams per 100 kilograms of seed, preferably 2.5 to 25 grams per 100 kilograms of seed, and preferably 2.5 to 12.5 grams per 100 kilograms of seed; from 0.1 to 10,000 grams per hectare when treating soil Preferably, it is from 1 to 5000 g/ha.

These rates of application are presented by way of example only and not as a limitation of the invention.

The active ingredient or composition of the invention thus protects the plant against the mentioned pathogen attack during a particular period of time after treatment. The period of protection is generally extended from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, optimally from 1 to 7 days, or up to after treatment of the seed, after treatment of the plant with the active ingredient. 200 days.

The method of treatment according to the invention also provides for the simultaneous or separate use or application of compounds (A) and (B) and/or (C). If a single active ingredient is administered in a continuous manner, i.e., at different times, it can be administered one after the other for a reasonably short period of time, such as hours or days. Preferably, the order in which the compounds (A) and (B) and/or (C) are applied is not essential to the operation of the invention.

The plants listed can be treated particularly advantageously in accordance with the invention with a compound of the formula (I) or a composition according to the invention. The preferred ranges of active ingredients or compositions referred to above are also suitable for treating such plants. Plants treated with the compounds or compositions specifically mentioned herein are of particular importance.

The invention is illustrated by the following examples. However, the invention is not limited to these examples.

Preparation example

The following compounds can be prepared by one or more of the methods described below.

The following compounds can be prepared by one or more of the methods described below.

The LogP value was measured by HPLC (High Performance Liquid Chromatography) on a reverse phase column in the following manner according to EEC directive 79/831 Annex V.A8: ^[a] LogP values are measured by LC-UV, in In the acidic range, it was determined using water with 0.1% formic acid and acetonitrile as the eluent (linear gradient of 10% acetonitrile to 95% acetonitrile).

The calibration system has a known LogP value (LogP is based on retention time) The linear alkane 2-ketone (with 3 to 16 carbon atoms) is measured by linear interpolation between two consecutive alkanones. The λ-maximum is determined using a UV-spectrum of 200 nm to 400 nm and a high peak of the chromatographic signal.

NMR-peak list

The 1H NMR data of the selected examples are shown in the form of a 1H-NMR-peak list. For each signal peak, the first series is the δ-value expressed in ppm, and then the signal strength in parentheses. The paired δ-value-signal intensity numbers are separated by a semicolon.

An example of a wave-peak list thus has the following form: δ ₁ (intensity ₁ ); δ ₂ (intensity ₂ ); ........; δ _i (intensity _i ); ...; δ _n (Strength _n ) In the example of the printed NMR spectrum (expressed in cm), the sharp signal intensity is related to the height of the signal and shows the true correlation of the signal strength. A wide signal that shows the middle of several peaks or signals compared to the strongest signal in the spectrum and its associated intensity.

For the calibration of the chemical shift of the 1H spectrum, we used the chemical shift of tetramethylnonane and/or the solvent used, especially in the case of the spectrum measured by DMSO. Therefore, in the NMR peak list, tetramethylnonane peaks may occur but are not necessarily.

The 1H-NMR peak list is similar to the orthodox 1H-NMR spectrum and therefore typically contains all of the peaks listed in the orthodox NMR-analytical map.

In addition, it may represent a formal 1H-NMR spectrum signal such as a solvent, a stereoisomer of the target compound, which is also an object of the present invention, and/or a peak of impurities.

The compound signal shown in the δ-range of solvent and/or water, the peak value of the general solvent, such as the peak of DMSO wave in DMSO-D ₆ and the peak value of water are shown on our 1H-NMR peak list. And usually it has a high intensity on average.

The peaks of the stereoisomers of the target compound and/or the peaks of the impurities generally have a lower average intensity (e.g., having >90% purity) than the peak of the target compound.

Such stereoisomers and/or impurities may be typical of a particular method of preparation. Therefore, its peak value can help identify the reproduction of our preparation method via "by-product fingerprints".

An expert who calculates the peak of the target compound by known methods (MestreC, ACD-simulation and empirically evaluated expected values), if necessary, uses an additional intensity filter to separate the peaks of the target compound. This separation should be similar to the correlation peak detection in the orthodox 1H-NMR spectrum.

A more detailed NMR-data description with a list of wave peaks can be found in the publication "Citation of NMR Peak List Data within Patent Applications" of the Research Disclosure Database Number 564025.

Experimental example Method a general process

3 ml of tetrahydrofuran and aminobenzobenzobutane of formula (III-a) (1 eq.) were placed in a Radley tube; triethylamine (0.17 ml, 1.2 eq) was added dropwise and the reaction mixture was stirred at room temperature. 10 minutes. Then, acid chloride (1.1 eq.) diluted with 1 ml of tetrahydrofuran was added dropwise and the mixture was refluxed for 2 hours. The reaction mixture was cooled at room temperature and 4 ml of water was added. The aqueous layer was extracted with dichloromethane, washed with water and dried over Chem Elut. Sometimes, without any purification, or by purification on a ruthenium column chromatography, the expected product of good purity is obtained (yield: 65% to 95%).

Method a general process

3 ml of tetrahydrofuran and the carboxylic acid of formula (II) (1.1 eq.) were placed in a Radley tube. Triethylamine (2 eq) was added dropwise followed by 4 eq. of polyphosphonic anhydride. The reaction mixture was stirred at room temperature for 30 minutes. Then, 1 eq. of the aminophenylbenzocyclobutane of the formula (III-a) (1.1 eq.) diluted with 1 ml of tetrahydrofuran was added dropwise. The mixture was refluxed overnight. The crude mixture was cooled at room temperature and 4 ml of water was added. The aqueous layer was extracted with dichloromethane, washed with water and dried over Chem Elut. Sometimes the desired product (yield: 35% to 74%) is obtained without any purification or by purification by column chromatography or preparative HPLC.

Method c general process

In a sealed microwave tube filled with argon, add 1,4-two dissolved in 20 ml 500 mg of the formula (III-b) 1-bromo-p-cyclobutane (1 eq) in the alkane. 324 mg of a third butylamine formazanate (1.5 eq), 117 mg of xantphos (0.1 eq), 1.2 g of cesium carbonate (2 eq) and 41 mg of palladium(II) acetate (0.1 eq) were continuously added. The tube was sealed and warmed to 100 °C over a 24 h period. The crude mixture was cooled at room temperature and water was added. The aqueous layer was extracted with dichloromethane, washed with water and dried over Chem Elut. After chromatography on a gum column, the expected product of formula (III-a) was obtained in 51% yield.

Method d general process

To a stirred solution of the compound of formula (vv) (0.3 g) in propane / diethyl ether (4:1), t-BuLi (3.2 eq.) was added at -78 ⁰ C. The reaction was stirred for 5 min and anhydrous THF (1 mL) was evaporated. The mixture was allowed to warm to room temperature. After 30 minutes, anhydrous 1,2-dibromoethane (0.5 ml) was added and stirred for 30 min. The reaction mixture was quenched with ice water at 0 ° C and ethyl acetate. The organic layer was washed with water and brine and evaporated, and then purified by column chromatography to afford 0.15 g of the compound of formula (III-b).

Method f general process

To a solution of the carboxylic acid (III-d) (1.0 eq.) in acetone (40 ml) was added dropwise at 0 ° C, TEA (1.5 eq.), iso-butyl chloroformate (1.3 eq. The mixture was stirred for 30 minutes, then a solution of NaN3 (2.0 eq.) in water (5.0 ml) was added to the mixture and stirred for 30 min. After the reaction was completed, the reaction mixture was diluted with ice water and ethyl acetate. The combined organic layers were washed with a brine solution, dried over anhydrous sodium sulfate and evaporated.

The stirred hydrazino azide (1.0 eq.) in benzyl alcohol (4.0 ml) was heated to 80 ° C for 16 hours. The crude reaction mixture was purified by column chromatography eluting with 15%EtOAcEtOAcEtOAc

To a solution of the above-preserved amine (1.0 eq.) in MeOH (20 mL) EtOAc. After completion of the reaction, the reaction mixture was filtered through celite (br.). The crude product was purified by silica gel column chromatography eluting with 20% EtOAc / petroleum ether to afford free amine (III-c).

Method g

Stirred solution of the aldehyde (III-e) (. 1.0eq ) of acetone: water (1: 1,40ml) was added sulfamic acid (. 1.1eq) at _{0 ℃, NaClO 2 (2.0g,} 23mmol, 1.1eq .) The reaction mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction mixture was diluted with ice water and ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated

Method h

To a solution of the aryl compound (vv) (1.0 eq.) in pentane: diethyl ether (5:1, 36 ml) was added to a solution of 1.6 M t-BuLi in pentane (3.2 eq.) at -78 ° C and the mixture was stirred. After 5 minutes, anhydrous THF (5.0 ml) was added and stirring was continued for 10 min. The reaction mixture was allowed to warm to room temperature over a period of 30 min then anhydrous DMF (1.0 eq.) was added and stirring was continued for 30 min. After completion of the reaction, the reaction mixture was quenched with EtOAc EtOAc. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated The crude product was purified by chromatography eluting with 7-10% EtOAc / petroleum ether to afford the desired aldehyde (III-e) (29%).

Example: In vivo prophylactic test of Botrytis cinerea ( Botrytis cinerea )

Solvent: 5% by volume of dimethyl hydrazine

10% by volume acetone

Emulsifier: 1 μl of Tween ^® 80 per mg of active ingredient

The active ingredient is dissolved and homogenized in a mixture of dimethyl hydrazine/acetone/Tween® 80 and then diluted with water to the desired concentration.

The young plants of the cucumber were treated by spraying the active ingredients prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl hydrazine/Tween® 80.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The infected cucumber plants were cultured for 4 to 5 days at 17 ° C and 90% relative humidity.

This test was evaluated 4 to 5 days after inoculation. 0% means the effect equivalent to the control plant, and 100% utility means that no disease is observed.

In the test, the following compounds of the invention exhibited an effect between 70% and 79% at an active ingredient concentration of 500 ppm: I-04.

The following compounds of the invention in this test exhibited a utility between 90% and 100% at an active ingredient concentration of 500 ppm: I-02; I-14; I-15.

The following compounds of the invention in this test exhibited an effect between 90% and 100% at an active ingredient concentration of 100 ppm: I-06; I-19.

Example: In vivo prophylactic test of Puccinia recondita (wheat brown rot)

Solvent: 5% by volume of dimethyl hydrazine

10% by volume acetone

Emulsifier: 1 μl of Tween ^® 80 per mg of active ingredient

The active ingredient is dissolved and homogenized in a mixture of dimethyl hydrazine/acetone/Tween® 80 and then diluted with water to the desired concentration.

Young plants of wheat are treated by spraying the active ingredients prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl hydrazine//Tween® 80.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of wheat leaf rust spores. The infected wheat plants were incubated at 20 ° C and 100% relative humidity for 24 hours and then incubated at 20 ° C and 70-80% relative humidity for 10 days.

This test was evaluated 11 days after inoculation. 0% means the effect equivalent to the control plant, and 100% utility means that no disease is observed.

The following compounds of the invention in this test exhibited a utility between 90% and 100% at an active ingredient concentration of 500 ppm: I-02; I-04; I-14; I-15.

The following compounds of the invention in this test exhibited a utility of 90% to 100% at an active ingredient concentration of 100 ppm: I-01; I-03; I-05; I-06; I-07; I-08; I-09; I-11; I-12; I-13; I-16; I-17; I-18; I-19; I-20;

Example: In vivo prophylactic test of Septoria tritici (wheat leaf blight)

Solvent: 5% by volume of dimethyl hydrazine

10% by volume acetone

Emulsifier: 1 μl of Tween ^® 80 per mg of active ingredient

The active ingredient is dissolved and homogenized in a mixture of dimethyl hydrazine/acetone/tween® 80 and then diluted with water to the desired concentration.

Young plants of wheat are treated by spraying the active ingredients prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl hydrazine/Tween® 80.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of S. glabrata spores. The infected wheat plants were cultured at 18 ° C and 100% relative humidity for 72 hours and then cultured at 20 ° C and 90% relative humidity for 21 days.

This test was evaluated 24 days after inoculation. 0% means the effect equivalent to the control plant, and 100% utility means that no disease is observed.

The following compounds of the invention in this test exhibited an effect between 80% and 89% at an active ingredient concentration of 500 ppm: I-02; I-04.

In the test, the following compounds of the invention exhibited an effect between 90% and 100% at an active ingredient concentration of 500 ppm: I-14; I-15.

The following compounds of the invention in this test exhibited a utility between 70% and 79% at an active ingredient concentration of 100 ppm: I-05; I-06.

In the test, the following compounds of the invention exhibited an effect between 80% and 89% at an active ingredient concentration of 100 ppm: I-01; I-07; I-11; I-18; I-19; I-20.

Example: In vivo prophylactic test of Sphaerotheca fuliginea (Gourd powdery mildew)

Solvent: 5% by volume of dimethyl hydrazine

10% by volume acetone

Emulsifier: 1 μl of Tween ^® 80 per mg of active ingredient

The active ingredient is dissolved and homogenized in a mixture of dimethyl hydrazine/acetone/Tween® 80 and then diluted with water to the desired concentration.

The young plants of the cucumber were treated by spraying the active ingredients prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl hydrazine/Tween® 80.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of the powdery mildew spores. The infected cucumber plants were cultured at 18 ° C and 100% relative humidity for 72 hours and then cultured at 20 ° C and 70-80% relative humidity for 12 days.

This test was evaluated 15 days after inoculation. 0% means the effect equivalent to the control plant, and 100% utility means that no disease is observed.

The following compounds of the invention in this test exhibited a utility between 80% and 89% at an active ingredient concentration of 500 ppm: I-04.

The following compounds of the invention in this test exhibited a utility between 90% and 100% at an active ingredient concentration of 500 ppm: I-02; I-14; I-15.

The following compounds of the invention in this test exhibited an effect between 80% and 89% at an active ingredient concentration of 100 ppm: I-05; I-19.

The following compounds of the invention in this test exhibited an effect between 90% and 100% at an active ingredient concentration of 100 ppm: I-06; I-17.

The following compounds of the invention in this test exhibited a utility between 90% and 100% at an active ingredient concentration of 10 ppm: I-11.

Example: In vivo prophylactic test of Uromyces appendiculatus (bean rust)

Solvent: 5% by volume of dimethyl hydrazine

10% by volume acetone

Emulsifier: 1 μl of Tween ^® 80 per mg of active ingredient

The active ingredient is dissolved and homogenized in a mixture of dimethyl hydrazine/acetone/Tween® 80 and then diluted with water to the desired concentration.

Young plants of kidney beans are treated by spraying the active ingredients prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl hydrazine/Tween® 80.

After 24 hours, the plants were infected by spraying the leaves with an aqueous suspension of the bean rust spores. The infected kidney bean plants were cultured at 20 ° C and 100% relative humidity for 24 hours and then cultured at 20 ° C and 70-80% relative humidity for 10 days.

This test was evaluated 11 days after inoculation. 0% means the effect equivalent to the control plant, and 100% utility means that no disease is observed.

The following compounds of the invention in this test exhibited a utility between 90% and 100% at an active ingredient concentration of 500 ppm: I-02; I-04; I-14; I-15.

In the test, the following compounds of the invention exhibited an effect between 90% and 100% at an active ingredient concentration of 100 ppm: I-01; I-03; I-05; I-06; I-07; I-08; I-09; I-11; I-12; I-13; I-16; I-17; I-18; I-19; I-20;

Example: In vivo prophylactic test of Phakopsora (soybean)

Solvent; 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

One part by weight of the active compound is mixed with the amount of solvent and emulsifier to produce a suitable preparation of the active compound, and the concentrate is diluted with water to the desired concentration.

The preparation of the active compound is sprayed on the young plants at the stated application rate for testing for prophylactic utility. After the sprayed layer is dried, the plant is inoculated with a spore suspension of the pathogenic pathogen of soybean rust [Phakopsora pachyrhizi ] and in an incubator at about 24 ° C and about 95% relative atmospheric humidity in the absence of light. Stay in place for 24 hours.

The plants were left in an incubator at about 24 ° C and about 80% relative atmospheric humidity and a 12 h day/night interval.

This test was evaluated 7 days after inoculation. 0% means the effect equivalent to the untreated control group, and 100% utility means that no disease is observed.

In the test, the following compounds of the invention exhibited a potency of 70% to 79% at an active ingredient concentration of 10 ppm: I-17.

The following compounds of the invention in this test exhibited an effect between 80% and 89% at an active ingredient concentration of 10 ppm: I-05; I-13.

Claims (16)

a benzocyclobutane (thio)carboxamide of the formula (I), Wherein the Ar system represents a group selected from the group consisting of Ar1 to Ar15: X ¹ , X ² , X ³ , X ⁴ and X ⁵ independently represent hydrogen; halogen; cyano; nitro, hydroxy; C ₁ -C ₁₆ -alkyl, having from 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl; C ₃ -C ₇ - cycloalkyl, having from 1 to 9 identical or different halogen atoms C ₃ -C ₇ - cycloalkyl, halogen; C ₁ -C ₆ - alkoxy a C ₁ -C ₆ -haloalkoxy group having 1 to 9 identical or different halogen atoms; a T system representing an oxygen or sulfur atom; and a Q system representing hydrogen, a C ₁ -C ₆ -alkylsulfonyl group, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl; X represents halogen, nitro, cyano, C ₁ -C ₁₂ -alkyl; C ₁ -C ₆ -haloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ - alkoxy; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkoxy; C ₁ -C ₆ - alkyl sulfanyl; having 1 to 9 identical or different halogen atoms, the C ₁ -C ₆ - haloalkyl sulfanyl; C ₁ -C ₆ - alkylsulfinyl acyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - alkylsulfinyl acyl halide group; C ₁ -C ₆ - alkyl sulfonamide Group; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl sulfo acyl; C ₂ -C ₁₂ - alkenyl; C ₂ -C ₁₂ - alkynyl; C ₃ -C ₇ - Cycloalkyl; phenyl; tri(C ₁ -C ₈ )alkylindenyl; tri(C ₁ -C ₈ )alkylindenyl-C ₁ -C ₈ -alkyl; m represents 0, 1, 2 Or 3; R ¹ , R ² , R ³ and R ⁴ independently of each other represent hydrogen; halogen; C ₁ -C ₁₆ -alkyl; C ₂ -C ₁₆ -halide having 1 to 9 identical or different halogen atoms Alkyl; C ₃ -C ₈ -cycloalkyl; C ₃ -C ₇ -halocycloalkyl having 1 to 9 identical or different halogen atoms; C ₁ -C having 1 to 9 identical or different halogen atoms ₆ -haloalkyl; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyl; (C ₃ -C ₈ -cycloalkyl)-C ₃ -C ₈ -cycloalkyl; C ₂ -C ₁₆ -alkenyl; C ₂ -C ₁₆ -alkynyl; C ₂ -C ₁₆ -alkenyl-C ₁ -C ₁₆ -alkyl; C ₂ -C ₁₆ -alkynyl-C ₁ -C ₁₆ - Alkyl; C ₁ -C ₁₆ -alkoxy; C ₃ -C ₈ -cycloalkyloxy; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyloxy; C ₁ -C ₈ -alkylsulfanyl; C ₃ -C ₈ -cycloalkylsulfanyl; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkylsulfanyl; C ₂ - C ₁₆ -alkenyloxy; C ₃ -C ₈ -alkynyloxy; aryl substituted by up to 6 identical or different R ^b groups as desired; aryl-C ₁ -C ₈ substituted by up to 6 identical or different R ^b groups, if desired - alkyl group; aryl group optionally substituted -C ₁ -C ₈ High 6 are the same or different R ^b groups of - alkylsulfanyl; an optionally-high six identical or different groups R ^b a aryloxy group substituted by a group; an arylsulfanyl group substituted with up to 6 identical or different R ^b groups as desired; (C ₃ -C ₈ -cycloalkyl)-C ₂ -C ₈ -alkenyl; (C ₃ -C ₈ -cycloalkyl)-C ₂ -C ₈ -alkynyl; tris(C ₁ -C ₈ )alkylindenyl; tris(C ₁ -C ₈ )alkylindenyl-C ₁ - C ₈ -alkyl; aryl-C ₁ -C ₈ -alkyl substituted by up to 6 identical or different R ^b groups, optionally substituted with up to 6 identical or different R ^b groups An aryl-C ₂ -C ₈ -alkenyl group; an aryl-C ₂ -C ₈ -alkynyl group substituted with up to 6 identical or different R ^b groups as desired; the limiting conditions are R ¹ , R ² , R ³ and R ⁴ do not simultaneously represent a carbon or hydrogen R ¹ and R ² lines connected thereto together represent C ₃ -C ₈ - cycloalkyl; C ₃ -C ₈ - cycloalkenyl, each optionally Department Substituted or R ¹ and R ² are representatives = C (Y ¹⁾ Y ² group or R ¹ and R ² are representatives containing 51 or two hetero atoms or a 6-membered ring and / or R ³ and R ⁴ Line and The linked carbons collectively represent C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, each of which is optionally substituted and/or R ³ and R ⁴ represent =C(Y ¹ )Y ^{The 2} group and/or R ³ and R ⁴ represent a 5- or 6-membered ring containing 1 or 2 heteroatoms or the R ¹ and R ³ systems together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group, C ₃ -C ₈ -cycloalkenyl, each of which is optionally substituted; R ^b represents halogen; nitro, cyano, C ₁ -C ₁₂ -alkyl; having from 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl; C ₁ -C ₆ - alkoxy; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkoxy; C ₁ -C ₆ - alkyl ylsulfanyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl sulfanyl; C ₁ -C ₆ - alkylsulfonyl group; having 1 to 9 identical or different halogen C ₁ -C ₆ -haloalkylsulfonyl; C ₂ -C ₁₂ -alkenyl; C ₂ -C ₁₂ -alkynyl; C ₃ -C ₇ -cycloalkyl;phenyl; tri(C ₁ -C ₈₎ alkyl silicon based; three (C ₁ -C ₈₎ Silicon based groups -C ₁ -C ₈ - alkyl; Y ¹ and Y ² independently of one another train represents hydrogen, halogen, C ₁ -C ₁₂ - alkyl; having a C 1 to 9 identical or different halogen atoms _1-- C ₆ -haloalkyl; C ₁ -C ₈ -alkylsulfanyl; phenyl; each of which is optionally substituted or Y ¹ and Y ² may form a C ₃ -C ₈ - ring together with the carbon to which they are attached Alkyl or C ₃ -C ₈ -cycloalkenyl or saturated 5, 6 or 7 membered heterocyclic rings; each of which is optionally substituted. The benzocyclobutane (thio)carboxamide of the formula (I), wherein the Ar system represents a group selected from the group consisting of Ar1, Ar2, Ar4, Ar7, Ar8, Ar10 and Ar13. X ¹ represents halogen; C ₁ -C ₁₆ -alkyl, C ₁ -C ₆ -haloalkyl having 1 to 9 identical or different halogen atoms; C ₃ -C ₇ -cycloalkyl, having 1 to 9 C ₃ -C ₇ -halocycloalkyl groups of the same or different halogen atoms; X ² , X ³ , X ⁴ and X ⁵ independently of each other represent hydrogen, halogen, C ₁ -C ₁₆ -alkyl, having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl; C ₃ -C ₇ - cycloalkyl group having a C 1 to 9 identical or different halogen atoms ₃ -C ₇ - cycloalkyl, halogen ; T represents an oxygen atom; Q represents hydrogen, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₁ -C ₄ -halide Alkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl having 1 to 9 fluorine, chlorine and/or bromine atoms in each case; X system represents fluorine , chloro, methyl or trifluoromethyl; m preferably represents 0, 1 or 2; R ¹ , R ² , R ³ and R ⁴ independently of each other represent hydrogen; halogen; C ₁ -C ₁₆ -alkane Base 1 to 9 identical or different halogen atoms C ₂ -C ₁₆ - haloalkyl; C ₃ -C ₈ - cycloalkyl; having 1 to 9 identical or different halogen atoms C ₃ -C ₇ - cycloalkyl halides a C ₁ -C ₆ -haloalkyl group having 1 to 9 identical or different halogen atoms; (C ₃ -C ₈ -cycloalkyl)-C ₁ -C ₈ -alkyl; (C ₃ -C ₈ -cycloalkyl)-C ₃ -C ₈ -cycloalkyl; C ₁ -C ₁₆ -alkoxy; C ₃ -C ₈ -cycloalkyloxy; (C ₃ -C ₈ -cycloalkyl)- C ₁ -C ₈ -alkyloxy; aryl substituted by up to 6 identical or different R ^b groups, if desired; aryl-C substituted by up to 6 identical or different R ^b groups, if desired ₁ -C ₈ -alkyloxy; aryl-C ₁ -C ₈ -alkyl substituted by up to 6 identical or different R ^b groups as desired; the restrictions are R ¹ , R ² , R ³ And R ^{4 may} not simultaneously represent hydrogen or the R ¹ and R ² systems together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group optionally substituted, wherein the substituent may be selected from halogen and C ₁ -C ₆ - The alkyl group and/or the R ³ and R ⁴ groups together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group optionally substituted, wherein the substituent may be selected from halogen and C ₁ -C ₆ -alkyl or R ¹ and R ^{The 3} series together with the carbon to which they are attached represent a C ₃ -C ₈ -cycloalkyl group optionally substituted, wherein the substituent may be selected from a halogen and a C ₁ -C ₆ -alkyl group; Y ¹ and Y ² are independently of each other Representing hydrogen, halogen, C ₁ -C ₁₂ -alkyl, C ₁ -C ₆ -haloalkyl having 1 to 9 identical or different halogen atoms or a carbon attached thereto to form an optionally substituted ring cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl group; R ^b represents halogen based; nitro, cyano, C ₁ -C ₈ - alkyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ -haloalkyl; C ₁ -C ₆ -alkoxy; C ₁ -C ₄ -haloalkoxy having 1 to 9 identical or different halogen atoms; C ₁ -C ₆ -alkylsulfanyl ; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ - haloalkyl sulfanyl; C ₁ -C ₆ - alkylsulfonyl group; having 1 to 9 identical or different halogen _{atoms. 1} C -C ₄ -haloalkylsulfonyl; C ₂ -C ₈ -alkenyl; C ₂ -C ₈ -alkynyl; C ₃ -C ₆ -cycloalkyl;phenyl;tri(C ₁ -C ₆ ) Alkyl fluorenyl; tri(C ₁ -C ₆ )alkylindolyl-C ₁ -C ₆ -alkyl. The benzocyclobutane (thio)carboxamide of the formula (I) of claim 1, wherein the Ar system represents a group selected from the group consisting of Ar1, Ar2 and Ar4; and the X ¹ system represents C ₁ - C ₁₂ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 9 identical or different halogen atoms; X ² , X ³ , X ⁴ and X ⁵ independently of each other represent hydrogen, fluorine, chlorine, bromine Iodine; C ₁ -C ₁₂ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 9 identical or different halogen atoms; T system representing an oxygen atom; Q system representing hydrogen, methylsulfonyl, Ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, second- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxy Methyl, ethoxyethyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; X particularly preferably represents fluorine, wherein the fluorine is preferably located in the benzocyclobutane 4-, 5- or 6-position, very particularly preferably at the 4- or 6-position; m particularly preferably represents 0 or 1; R ¹ , R ² , R ³ and R ⁴ independently of each other represent hydrogen; halogen; C ₁ -C ₁₆ - alkyl; having 1 to 9 identical or different halogen atoms C ₂ -C ₁₆ - haloalkyl; C ₃ -C ₈ - cycloalkyl; 1 to 9 identical or different halogen atoms C ₃ -C ₇ - cycloalkyl halo; having 1 to 9 identical or different halogen atoms C ₁ -C ₆ - haloalkyl; (C ₃ -C ₈ - Cycloalkyl)-C ₁ -C ₈ -alkyl; (C ₃ -C ₈ -cycloalkyl)-C ₃ -C ₈ -cycloalkyl; C ₁ -C ₁₆ -alkoxy; the substituted six R ^b are the same or different aryl group; optionally substituted six-high of the same or different R ^b groups aryl -C ₁ -C ₈ - alkyl; with the proviso that R ^1, R ² , R ³ and R ^{4 may} not simultaneously represent hydrogen or the R ¹ and R ² systems together with the carbon to which they are attached represent a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group optionally substituted. The carbon, which may be selected from the group consisting of fluorine, chlorine, methyl and ethyl and/or R ³ and R ⁴ , together with the carbon to which they are attached, represents a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group which may be optionally substituted. The substituent may be selected from the group consisting of fluorine, chlorine, methyl and ethyl; Y ¹ and Y ² independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl; ethyl, propyl, isopropyl; R ^b represents fluorine, chlorine, bromine; C ₁ -C ₆ - alkyl; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ - haloalkyl; C ₁ -C ₄ - alkoxy; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ - haloalkoxy; C ₁ -C ₄ - alkylsulfanyl ; having 1 to 9 identical or different halogen atoms C ₁ -C ₄ - haloalkyl sulfanyl; C ₁ -C ₄ - alkylsulfonyl group; having 1 to 9 identical or different halogen _{atoms. 1} C -C ₄ -haloalkylsulfonyl; C ₂ -C ₆ -alkenyl; C ₂ -C ₆ -alkynyl; C ₃ -C ₆ -cycloalkyl;phenyl; tris(C ₁ -C ₄ ) Alkyl fluorenyl; tri(C ₁ -C ₄ )alkylindolyl-C ₁ -C ₄ -alkyl. The benzocyclobutane (thio)carboxamide of the formula (I), wherein the Ar system represents a group selected from the group consisting of Ar2 and Ar4; and the X ¹ represents a difluoromethyl group; X ² , X ³ and X ⁴ represent each other independently of fluorine and chlorine; T represents an oxygen atom; Q represents hydrogen; m represents 0; and R ¹ , R ² , R ³ and R ⁴ independently of each other represent hydrogen. Hydrogen; phenyl, ethyl, methyl, prop-2-yl; the limitation is that R ¹ , R ² , R ³ and R ⁴ cannot simultaneously represent hydrogen or R ³ and R ⁴ are co-linked with the carbon to which they are attached Represents a cyclopentyl group or a cyclohexyl group which is substituted as needed. A process for the preparation of a benzocyclobutane (thio)carboxamide of the formula (I) according to the first aspect of the patent application, characterized in that the compound of the formula (II) is used in the first step Wherein Ar is as defined in the first paragraph of the patent application, and the Z system represents a halogen, a cyano group, a hydroxyl group or an activated hydroxyl group, and reacts with a compound of the formula (III-a). Wherein Q, X, m, R ¹ , R ² , R ³ , R ⁴ are as defined in the first item of the patent application, to obtain a compound of the formula (Ia) Wherein Ar, Q, X, m, R ¹ , R ² , R ³ , R ⁴ are as defined in claim 1 of the patent application, and in the case where the compound T of the formula (I) represents sulfur, in the second In the step, the compound of the formula (Ia) is reacted with a compound of the formula (Ib) in the presence of a vulcanizing agent. Wherein Ar, Q, X, m, R ¹ , R ² , R ³ and R ⁴ are as defined in the first item of the patent application. A process for the preparation of a compound of the formula (III-a), characterized in that a bromide of the formula (III-b) is reacted with a compound of the formula (IV) or (V) in the presence of a catalyst and a diluent, followed by Acid treatment, wherein Q, X, m, R ¹ , R ² , R ³ and R ⁴ are as defined in the first item of the patent application, and Y represents hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl Oxyl, phenoxy, benzyloxy. A process for the preparation of a compound of the formula (III-b), characterized in that the iodide of the formula (VV) is cyclized in the presence of a vehicle, a brominating agent and in the presence of a diluent, wherein Q, X, m, R ¹ , R ² , R ³ and R ⁴ are as defined in the first item of the patent application. A process for the preparation of a compound of the formula (III-b), characterized in that an iodide of the formula (VI) is reacted with a compound of the formula (VII) in the presence of a base and a diluent, wherein X, m, R ¹ , R ² , R ³ and R ⁴ are as defined in the first item of the patent application. The method of claim 8, wherein R ¹ and R ² represent a C ₁ -C ₁₆ -alkoxy group. a compound of formula (III-a), Wherein Q, X, m, R ¹ , R ² , R ³ and R ⁴ are as defined in the first item of the patent application. a compound of formula (III-b), Wherein X, m, R ¹ , R ² , R ³ and R ⁴ are as defined in the first item of the patent application. A composition for controlling phytopathogenic harmful fungi, characterized by comprising at least one compound of the formula (I) according to any one of claims 1 to 4, an additional extender and/or a surfactant. A method for controlling a phytopathogenic harmful fungus, which is characterized in that the compound of the formula (I) according to any one of claims 1 to 4 is applied to a phytopathogenic harmful fungus and/or its habitat. A use of a compound of the formula (I) according to any one of claims 1 to 4 or a composition according to claim 6 of the patent application for the control of phytopathogenic harmful fungi. A method for producing a composition for controlling a phytopathogenic harmful fungus, characterized by mixing a compound of the formula (I) according to any one of claims 1 to 4 with a bulking agent and/or a surfactant . A use of a compound of the formula of any one of claims 1 to 4 or a composition of claim 6 of the patent application for the treatment of seeds of genetically transgenic plants, seeds and genetically transformed plants.