Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/10—Antimycotics
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
  • C07D303/02—Compounds containing oxirane rings
  • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
  • C07D303/02—Compounds containing oxirane rings
  • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
  • C07D303/02—Compounds containing oxirane rings
  • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
  • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
  • C07D303/02—Compounds containing oxirane rings
  • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

• B is phenyl which is unsubstituted or substituted by one, two, three or four identical or different substituents L, where L is
• L is halogen, cyano, nitro, cyanato (OCN), C -C 8 -alkyl, C 8 -HaIo- genalkyl, phenyl-Ci-C ⁇ -alkyloxy, C2-C8 alkenyl, C2-C8 haloalkenyl , C2-C8 alkynyl, C2-C8 haloalkynyl, C4-Cio-alkadienyl, C4-Cio-alkadienyl halogen, Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyloxy, d- Cs-alkylsulfonyloxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C2-C 8 -
• n 0, 1 or 2;
• a 1 is hydrogen, hydroxy, Ci-C 8 alkyl, Ci-C8-haloalkyl, amino,
• One of said at A 1 or A 2 groups C2-C8 alkenyl, C2-C 8 - haloalkenyl, C2-C8 alkynyl, C2-C8-haloalkynyl, Ci-C 8 -AIk- oxy, Ci-C 8 haloalkoxy, C2-C8 alkenyloxy, C2-C8-halo alkenyloxy, C2-C8-alkynyloxy, C2-C8 haloalkynyloxy, Cs-C 8 - cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8 cycloalkoxy or C3-C8-halocycloalkoxy;
• a 3, A 4 are independently hydrogen, Ci-C 8 alkyl, Ci-C 8 -HaIo- genalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8 alkynyl, C2-C8-haloalkynyl, C3 -C 8 -cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkenyl or C3-Cs-halocycloalkenyl;
• R L is halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy, C 1 -C 8 -cycloalkyl, C 1 -C 8 -halocycloalkyl, C 3 -C 8 -cycloalkenyl , Cs-Cs-cycloalkoxy, C3-C 8 -Halogencyclo- alkoxy, Ci-Cs-alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, Ci-C 8 - alkoxycarbonyl, amino, Ci-Cs-alkylamino, di-Ci-Cs-alkylamino ;
• R 3 is Ci-Cs-alkyl, d-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-C 8 - haloalkoxy or NA 3 A 4 ;
• R 4 is Ci-Cs-alkyl, phenyl-Ci-C 8 -alkyl or phenyl, wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and Ci-d-alkyl;
• R 1 , R 2 independently of one another are C 1 -C 6 -alkyl, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkoxy, C 1 -C 5 -alkoxy-C 1 -C 5 -alkoxy, C 1 -C 8 -haloalkoxy, C 1 -C 8 -alkoxy-C 1 -Cs-alkyl, CrC 8 -AI alkyl thio, C 2 -C 8 -alkenylthio, C 2 -C 8 -alkyl kinyl- thio, Cs-Cs-cycloalkyl, C 3 -C 8 cycloalkylthio, phenyl, phenyl-CrC 4 -alkyl, phenoxy, phenylthio, phenyl-C 1 -C 4 -alkoxy or NR 5 R 6 , wherein R 5 is H or C 1 -C 8
• M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
• Z 1 and Z 2 are independently hydrogen or C 1 -C 8 alkyl
• Z 3 and Z 4 are independently hydrogen, C 1 -C 8 alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
• the compounds of the formula I can be present in the "thiol” form of the formula Ia or in the "thiono” form of the formula Ib: ! a Ib
• R wherein R has the meaning defined above;
• the invention relates to the preparation of the compounds I, the intermediates for the preparation of the compounds I and their preparation and the use of the compounds according to the invention for controlling phytopathogenic fungi and agents containing them.
• Triazolylmethyloxiranes having substituted triazole group e.g. from WO 96/38440, WO 97/41107, WO 97/42178, WO 97/43269, WO 97/44331, WO 97/443332, WO 99/05149 and WO 99/21853.
• the fungicidal action of the compounds known from the prior art leaves something to be desired, in particular at low application rates in some cases. It is an object of the present invention to provide novel compounds which preferably have improved properties, such as a better fungicidal action and / or better toxicological properties. This object has surprisingly been achieved with the compounds of the formula I described herein.
• the compounds I are able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them. This also applies to most of the herein described precursors for compounds I, of which the salts and adducts are also the subject of the present invention.
• inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
• Suitable organic acids are, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic Radicals such as phenyl and naphthyl which carry one or two phospho
• the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others in consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
• the metals can be present in the various valences that belong to them.
• the compounds of the formula I according to the invention can be prepared in various ways in analogy to prior art processes known per se (see, for example, the cited prior art and entitledgeber-Nachlet Bayer 57/2004, 2, pages 145-162).
• the compounds of the invention can be prepared by the syntheses shown in the following Schemes.
• Suitable bases are all suitable bases known to those skilled in the art for such reactions.
• strong alkali metal bases such as n-butyl lithium, lithium diisopropylamide, sodium hydride, sodium amide or potassium tert-butoxide are used. It may be preferable to carry out the reaction in the presence of an additive such as tetramethylethylenediamine (TMEDA).
• TEDA tetramethylethylenediamine
• Suitable solvents are all inert organic solvents which are customary for such reactions, ethers such as tetrahydrofuran, dioxane, diethyl ether and 1, 2-dimethoxyethane or liquid ammonia or strongly polar solvents such as dimethyl sulfoxide preferably being usable.
• Sulfur is preferably used as a powder.
• Hydrolysis is carried out using water, optionally in the presence of an organic or inorganic acid, e.g. Acetic acid, dilute sulfuric acid or dilute hydrochloric acid.
• an organic or inorganic acid e.g. Acetic acid, dilute sulfuric acid or dilute hydrochloric acid.
• the reaction temperature is preferably between -70 0 C and + 20 0 C, in particular between -70 0 C and 0 0 C.
• the reaction is generally carried out under atmospheric pressure.
• reaction may be carried out under a protective gas atmosphere, e.g. under nitrogen or argon.
• the workup is carried out according to methods generally known to the person skilled in the art.
• the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography.
• the reaction is usually carried out at temperatures in the range of 140 0 C to 160 0 C.
• the reaction components are usually employed in amounts such that about 1 to 6 moles of sulfur are used per mole of compound II.
• Sulfur is usually used in the form of powder. During the reaction, air is passed over the reaction mixture.
• R is C1-C8 alkyl, C1-C8 haloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 Haloalkynyl or CN can mean.
• Suitable bases are all suitable bases known to those skilled in the art for such reactions.
• strong alkali metal bases such as n-butyl lithium, lithium diisopropylamide, sodium hydride, sodium amide or potassium tert-butoxide are used. It may be preferred to react in the presence of an additive such as e.g. Tetramethylethylenediamine (TMEDA) to perform.
• TEDA Tetramethylethylenediamine
• the disulfides are commercially available or synthesized by known manufacturing methods.
• a special disulfide is the Dirhodan NC-S-S-CN.
• Suitable solvents are all inert organic solvents which are customary for such reactions, ethers such as tetrahydrofuran, dioxane, diethyl ether and 1, 2-dimethoxyethane or liquid ammonia or strongly polar solvents such as dimethyl sulfoxide preferably being usable.
• the reaction temperature is preferably between -70 ° C and +20 0 C, in particular between -70 ° C and 0 ° C.
• the reaction is generally carried out under normal pressure. In general, 1 to 3 equivalents, preferably 1 to 2.5 equivalents, of strong base and then an equivalent amount or an excess of disulfide are used per mole of the compound of the formula II.
• the reaction can be carried out under a protective gas atmosphere, for example under nitrogen or argon.
• the processing takes place according to methods generally known to the person skilled in the art. Usually, the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography.
• R-X is a leaving group, such as e.g. Halogen, such as Cl, Br or I, or trifluoro-Ci-C ⁇ -alkyl sulfonate
• X is a leaving group, such as e.g. Halogen, such as Cl, Br or I, or trifluoro-Ci-C ⁇ -alkyl sulfonate
• a compound 1-1 is reacted with the corresponding alkyl halide (see also WO 96/38440).
• Z is a leaving group X (Compounds III.1, see below) or OH (Compounds III.2, see below) and A and B are as defined below, are important starting compounds to ultimately arrive at the compounds of the invention.
• X is a leaving group such as, for example, halogen (eg Cl or Br) or OSO 2 R, where R is C 1 -C 6 -alkyl, d-Ce-haloalkyl, aryl or substituted aryl, in particular OSO 2 R for a mesylate, triflate, phenyl or toluenesulfonate group.
• a base such as, for example, sodium hydride in, for example, DMF. See also eg EP 0 421 125 A2.
• An object of the invention are therefore also compounds of formula III.1, wherein A and B are as defined for formula I or are preferably defined, and X is a leaving group, in particular halogen (eg Cl or Br) or OSO 2 R, wherein R is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, aryl or substituted aryl, where the compounds are anti-2- (2,4-difluorophenyl) -2- (chloromethyl) -3- (4 -chlorophenyl) oxirane, anti-2- (2,4-difluorophenyl) -2- (chloromethyl) -3- (3-chlorophenyl) oxirane, anti-2- (2,4-difluorophenyl) -2- (chloromethyl) - 3- (3,4-dichlorophenyl) oxirane, anti-2- (2,4-diflu
• B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl. Further, according to another embodiment of III.1, B is not ortho-methylphenyl when A is 2,4-difluorophenyl.
• B is not ortho or para trifluoromethylphenyl. In another specific embodiment, B also does not mean ortho-methylphenyl.
• X does not mean CH 3 SO 2 O or 4-CH 3 -phenyl-SO 2 -O.
• a and B have the meanings as specified for Formula I herein, taking into account the excluded compounds.
• X is as for formula III.1 and A and B are as defined or preferably defined for formula I.
• Suitable epoxidation processes are known to the person skilled in the art. For example, hydrogen peroxide / maleic anhydride can be used for this purpose.
• the double bond may exist in both (E) and (Z) configurations. This is represented by the jagged bond between B and the double bond.
• a further subject of the present invention are compounds of the formula IVa, in which A and B are as defined or preferably defined for formula I, where the compounds are (Z) -1- [3-chloro-1- (4-chlorophenyl) propyl] 1-en-2-yl] -2,4-difluorobenzene, (Z) -1 - [3-chloro - (3-chlorophenyl) prop-1 -en-2-yl] -2,4-difluorobenzene, (Z ) -1 - [3-Chloro - (3,4-dichlorophenyl) prop-1 -en-2-yl] -2,4-difluorobenzene, (Z) -1 - [3-chloro-2-fluorophenyl) prop -1-en-2-yl] -2,4-
• B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl. According to another embodiment, B is not ortho-methylphenyl when A is 2,4-difluorophenyl.
• B is not ortho or para trifluoromethylphenyl. In another specific embodiment, B also does not mean ortho-methylphenyl.
• a and B in IVa have the meanings as specified for Formula I herein, taking into account the excluded compounds.
• An object of the invention are therefore also compounds of the formula IVc, in which A and B are as defined for formula I or are preferably defined, wherein the compounds 1-chloro-2- (2,4-difluorophenyl) -3- (4- chlorophenyl) propan-2-ol, 1-chloro-2- (2,4-difluorophenyl) -3- (3-chlorophenyl) propan-2-ol, 1-chloro-2- (2,4-difluorophenyl) -3 - (3,4-dichlorophenyl) propan-2-ol, 1-chloro-2- (2,4-difluorophenyl) -3- (2-fluorophenyl) propan-2-ol, 1-chloro-2 ( 2,4-difluorophenyl) -3- (3,4-difluoro phenyl) propan-2-ol, 1-chloro-2- (2,4-d
• B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl. According to another embodiment, B is not ortho-methylphenyl when A is 2,4-difluorophenyl. In a particular embodiment, B is not ortho or para-trifluoromethylphenyl. In another specific embodiment, B also does not mean ortho-methylphenyl.
• a and B in IVc have the meanings as specified for Formula I herein, taking into account the excluded compounds.
• Compounds IVc are accessible, for example, via a Grignard reaction according to the following scheme:
• a compound of the formula III.2 is obtained, for example, with R-SO 2 Y, where R is as defined for formula III.1 and Y is halogen, where R-SO 2 Y is, for example, mesyl chloride, in the presence of a base (for example NEt. 3) reacted (see also EP386557).
• R-SO 2 Y is, for example, mesyl chloride
• a base for example NEt. 3
• a compound III.2 can be reacted with SOCl 2 / pyridine (see also WO 2005/056548).
• Compounds of the formula III.2 are partly new.
• An object of the present invention are therefore also compounds of formula III.2, wherein A and B are as defined or preferably defined for formula I, wherein the compounds 2-hydroxymethyl-2- (2,4-difluorophenyl) -3- ( 2-trifluoromethylphenyl) oxirane and 2-hydroxymethyl-2- (2,4-difluorophenyl) -3- (4-trifluoromethylphenyl) oxirane are excluded.
• B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl. According to another embodiment, B is not ortho-methylphenyl when A is 2,4-difluorophenyl.
• B is not ortho or para trifluoromethylphenyl. In another specific embodiment, B also does not mean ortho-methylphenyl.
• a and B in III.2 have the meanings as specified for Formulas I and III.1 herein, taking into account the excluded compounds.
• the double bond may be in both (E) and (Z) configurations. This is represented by the jagged bond between B and the double bond.
• Compounds of formula V are partially new.
• An object of the invention are therefore also compounds of the formula V, wherein A and B are as defined or preferably defined for formula I, wherein the compounds 2- (2,4-difluorophenyl) -3- (2-trifluoromethylphenyl) propenal and 2 - (2,4-difluorophenyl) -3- (4-trifluoromethylphenyl) propenal are excluded.
• B is not ortho-methylphenyl when A is 2,4-difluorophenyl. In another embodiment, B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl.
• B is not ortho or para trifluoromethylphenyl. In another specific embodiment, B also does not signify ortho-methylphenyl.
• a and B in V have the meanings as specified for formula I herein, taking into account the excluded compounds.
• B is not ortho-methylphenyl when A is 2,4-difluorophenyl. According to a particular embodiment, B is not ortho or para trifluoromethylphenyl. According to another specific embodiment, B is not ortho-methylphenyl.
• a and B in Va have the meanings as specified for Formula I herein, taking into account the excluded compounds.
• Each R y is independently C 1 -C 4 -alkyl.
• Suitable oxidizing agents and conditions are known to those skilled in the art. For example, a reaction according to Swern (Australian Journal of Chemistry, 57 (6), 537-548, 2004), reactions with hypervalent iodine compounds (Organic Letters, 5 (17), 2989-2992, 2003), with chromium compounds such as, for example, pyridinium di chromate (cf. Tetrahedron, 45 (1), 239-58, 1989) or with manganese oxides such as MnO 2 (Journal of the American Chemical Society, 107 (13), 3963-71, 1985).
• the oxidation can also be carried out via a Dess-Martin oxidation in a solvent such as CH 2 Cl 2.
• the double bond can be in both (E) and (Z) configurations. This is represented by the serrated bond between B and the double bond.
• B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl. In a particular embodiment, B is not ortho or para-trifluoromethylphenyl.
• a and B in VII have the meanings as specified for Formula I herein, taking into account the excluded compounds.
• esters of the formula VIII are reduced to the alcohol VII.
• Suitable reduction methods are well known to those skilled in the art.
• the double bond may be in both (E) and (Z) configurations. This is represented by the jagged bond between B and the double bond.
• Some of the compounds of formula VIII are novel and these are also the subject of the present invention.
• a and B in the compounds VIII have the meanings as specified for formula I herein, taking into account the excluded compounds.
• Compounds of formula VIII may also be reduced in one step to the acrolein of formula V, e.g. with metal hydrides, e.g. Diisobutylaluminum hydride at low temperatures.
• metal hydrides e.g. Diisobutylaluminum hydride at low temperatures.
• metal hydrides e.g. Diisobutylaluminum hydride at low temperatures.
• aluminum hydrides preferably lithium alanate (European Journal of Medicinal Chemistry, 40 (6), 529-541, 2005) or dialkylaluminum hydrides, such as e.g. DIBAL-H (Synlett, (18), 3182-3184, 2006) can be used here.
• the acrylic esters of formula VIII are available from glyoxylic esters of formula IX by reaction with phosphorus compounds, e.g. Horner-Emmons type or Wittig connections.
• Suitable phosphorus compounds can be prepared by known standard methods, for example from a compound of the following type:
• X 1 represents a leaving group such as a halide, preferably chlorine or bromine.
• a leaving group such as a halide, preferably chlorine or bromine.
• the reaction of such halides to the desired Horner-Emmons or Wittig reagents can be carried out as described, for example, in Chemistry of Materials, 13 (9), 3009-3017; 2001, European Journal of Organic Chemistry, (7), 1247-1257; 2005 or WO1992 / 05145.
• alkyl halides are either commercially available or can be prepared by standard methods, e.g. by halogenation of the corresponding methyl compound.
• Suitable halogenating agents for this reaction are N-bromosuccinimide (Chemistry-A European Journal, 12 (21), 5632-5641, 2006) and N-chlorosuccinimide (Tetrahedron Letters, 47 (37), 6607-6609, 2006).
• the double bond may be in both (E) and (Z) configurations. This is indicated by the jagged bond between B and the double bond. posed.
• Another object of the present invention are compounds of formula IVb, wherein A and B are as defined or preferably defined for formula I.
• B is not ortho or para-trifluoromethylphenyl when A is 2,4-difluorophenyl. In a particular embodiment, B is not ortho or para-trifluoromethylphenyl.
• B furthermore does not signify ortho-methylphenyl when A is 2,4-difluorophenyl. According to a specific embodiment, B is not ortho-methylphenyl.
• a and B in IVb have the meanings as specified for Formula I herein, taking into account the excluded compounds.
• Compounds of formula IVb can be obtained by reacting a compound of formula IVa, as shown above, with 1, 2,4-triazole and a base.
• the reaction conditions can be selected as described above in the preparation of compounds II starting from compounds III.
• An object of the present invention are also compounds of the formula IIIa, wherein A and B are as defined or preferably defined for formula I.
• An object of the present invention are also compounds of the formula INb, wherein A and B are as defined or preferably defined for formula I.
• compounds IIIa may be reacted with formaldehyde ((CHbO) n ) and a thiocyanate (YSCN, supra) to give
• An object of the present invention are also compounds of the formula INc, wherein A and B are as defined or preferably defined for formula I.
• R x1 and R x2 are preferably both methyl (compounds IIId-1). See also DE19744401 and WO99 / 18086.
• An object of the present invention are furthermore compounds of the formula INd, wherein A and B are as defined or preferably defined for formula I.
• Halogen fluorine, chlorine, bromine and iodine
• Haloalkyl alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above; in particular C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 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, 2,2,2-trichloroethyl, pentafluoroethyl or 1, 1 , 1-
• Alkenyl and the alkenyl moieties in compounded groups such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position.
• alkenyl groups such as (C 2 -C 4) alkenyl
• larger alkenyl groups such as (C 5 -C 8) alkenyl. Examples of alkenyl groups are e.g.
• C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 Methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propen
• Haloalkenyl alkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
• Alkadienyl unsaturated, straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position;
• Alkynyl as well as the alkynyl moieties in compounded groups straight or branched chain hydrocarbon groups of 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-he
• Haloalkynyl alkynyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
• Cycloalkyl and the cycloalkyl moieties in assembled groups mono- or bicyclic, saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, e.g. C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
• Halogencycloalkyl cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
• Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, Cyclohexene-4-yl and the like;
• Halocycloalkenyl cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
• Alkoxy for an oxygen-bonded alkyl group as defined above, preferably having 1 to 8, more preferably 2 to 6 carbon atoms. Examples are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; as well as e.g.
• Pentoxy 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3 Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy , 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
• Haloalkoxy alkoxy as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine.
• halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine.
• examples of these are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2 Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-
• Alkylene divalent linear chains of CH 2 groups. Preference is given to (C 1 -C 6) -alkylene, more preferably (C 2 -C 4) -alkylene, and furthermore it may be preferable to use (C 1 -C 3 ) -alkylene groups.
• alkylene radicals are CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 (CH 2 ) 2 CH 2 , CH 2 (CH 2 ) 3 CH 2 and CH 2 (CH 2 ) 4 CH 2 ; 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S, wherein the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
• tri- or four-membered saturated heterocycle (hereinafter also Heterocyc IyI) containing one or two heteroatoms from the group O, N and S as ring members; - five- or six-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group O, N and S as ring members: eg monocyclic saturated or partially unsaturated Heterocyc- len, containing in addition to carbon ring members one, two or three nitrogen atoms and or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2
• hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1H] oxepin-2, 3, -4, 5, 6 or 7-yl, 2,3,4, 7-tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1 H] oxepin 2-, -3-, -A-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3- or -4-yl, tetra- and hexahydro-1, 3 diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl
• the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred for the heterocycle to be bonded via nitrogen.
• the heterocycle means in particular:
• 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5- ring heteroaryl groups which may contain, in addition to carbon atoms, one to four nitrogen atoms or one, two or three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, especially 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl,
• novel compounds of this invention contain chiral centers and are generally obtained in the form of racemates or as diastereomeric mixtures of erythro and threo forms.
• the erythro and threo diastereomers can be separated in the compounds of the invention, for example, due to their different solubility or by column chromatography and isolated in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers.
• antimicrobial agents can be used both the uniform diastereomers or enantiomers as well as their resulting in the synthesis of mixtures. The same applies to the fungicides.
• the invention therefore relates both to the pure enantiomers or diastereomers and to mixtures thereof.
• the scope of the present invention includes the (R) and (S) isomers and the racemates of the compounds of the invention, in particular of the formula I or II, which have chiral centers.
• Suitable compounds according to the invention, in particular of the formula I or II also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
• the compounds according to the invention in particular of the formula I or II, can be present in various crystal modifications whose biological activity can be different. These are included in the scope of the present invention.
• A is phenyl substituted with an F and containing another substituent L other than Br, which phenyl may additionally contain one or two independently selected substituents L.
• A is according to a preferred embodiment for a group A-1 wherein # represents the point of attachment of the phenyl ring to the oxirane ring;
• L 2 is selected from F, Cl, NO 2 , phenyl, halophenyl, phenoxy, halophenyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -haloalkylthio;
• L 3 is independently selected from F, Cl, Br, NO 2, phenyl, halophenyl, phenoxy,
• Halophenoxy C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy
• L 2 in one embodiment is selected from F, Cl, methyl, methoxy, CF 3, CHF 2, OCF 3, OCF 3 and OCHF 2. In a more specific embodiment, L 2 is F or Cl.
• L 3 is independently selected from F, Cl, methyl, methoxy, CF 3, CHF 2, OCF 3, OCF 3 or OCHF 2 in one embodiment. In a more specific embodiment, L 3 is independently F or Cl.
• the fluoro substituent according to a preferred embodiment is in the 4-position.
• A is di-substituted phenyl which has one F and one further substituent L selected from Cl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -alkoxy, in particular selected from Cl, Methyl, trifluoromethyl and methoxy.
• the second substituent L is selected from methyl, methoxy and chloro. According to one embodiment thereof, one of the substituents is in the 4-position of the phenyl ring.
• the phenyl ring A is substituted in the 2,4-position.
• A is phenyl which is substituted by exactly two F.
• A is 2,3-difluoro substituted.
• A is 2,4-difluoro-substituted.
• A 2,5-difluoro-substituted.
• A is 2,6-difluoro-substituted.
• A is 3,4-difluoro-substituted.
• A is 3,5-difluoro substituted.
• A is phenyl substituted with exactly three F.
• A is 2,3,4-trifluoro-substituted.
• A is 2,3,5-trifluoro-substituted.
• A is 2,3,6-trifluoro-substituted.
• A is 2,4,6-trifluoro-substituted.
• A is 3,4,5-trifluoro substituted.
• A is 2,4,5-trifluoro-substituted.
• B is unsubstituted phenyl.
• B represents phenyl which contains one, two, three or four independently selected substituents L.
• the phenyl ring is monosubstituted with a substituent L, wherein L is according to a particular embodiment of this embodiment in ortho position to the point of attachment of the phenyl ring with the oxirane ring.
• B represents phenyl which contains one, two or three independently selected substituents L as defined below.
• B is phenyl which is substituted by one, two or three halogen atoms.
• B is a phenyl ring which contains a substituent L in the ortho position and also has a further independently selected substituent L.
• the phenyl ring is 2,3-disubstituted.
• the phenyl ring is 2,4-disubstituted.
• the phenyl ring is 2,5-disubstituted.
• the phenyl ring is 2,6-disubstituted.
• B is a phenyl ring which contains a substituent L in the ortho position and also contains two further independently selected substituents L.
• the phenyl ring is 2,3,5-trisubstituted.
• the phenyl ring is 2,3,4-trisubstituted.
• the phenyl ring is 2,4,5-trisubstituted.
• B is not ortho-methylphenyl. In another embodiment of the invention, B is not ortho or para trifluoromethylphenyl.
• L independently has the following preferred meanings:
• a 1 is hydrogen, hydroxy, Ci-C 4 -alkyl, Ci-C4-haloalkyl;
• a 2 is one of the groups mentioned at A 1 or C 1 -C 4 -alkoxy, C 1 -C 4 -
• Haloalkoxy C 3 -C 6 -cycloalkyl, Cs-C ⁇ -halocycloalkyl, C 3 -C ⁇ -cycloalkoxy or C 3 -C 6 -halocycloalkoxy;
• a 3 , A 4 independently of one another are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl;
• R L is halogen, cyano, nitro, Ci-C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 - alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, Cs-C ⁇ -halocycloalkyl,
• L is independently selected from halogen, NO2, amino, -C 4 - alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4 alkylamino, di- Ci- C 4 -alkylamino, thio and C 1 -C 4 -alkylthio.
• L is independently selected from halogen, Ci-C4-alkyl, Ci-C 4 - haloalkyl, Ci-C4-alkoxy, Ci-C4 haloalkoxy, and Ci-C4-haloalkylthio.
• L is independently selected from F, Cl, Br, CH 3, C 2 H 5, iC 3 H 7, tC 4 H 9, OCH 3, OC 2 H 5, CF 3, CCl 3, CHF 2 , CCIF 2 , OCF 3 , OCHF 2 and SCF 3 , in particular selected from F, Cl, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , CF 3 , CHF 2 , OCF 3 , OCHF 2 and SCF 3 , According to one embodiment, L is independently selected from F, Cl, CH 3, OCH 3, CF 3, OCF 3 and OCHF. 2 It may be preferred that L is independently F or Cl. In a preferred embodiment, the present invention relates to compounds of the formula I in which the variables have the following meanings:
• n 0, 1 or 2;
• a 1 is hydrogen, hydroxy, C 1 -C 8 -alkyl, C 1 -C 5 -haloalkyl, amino, C 1 -C 8 -alkylamino or C 1 -C 8 -alkylamino,
• a 2 is one of the groups mentioned at A 1 or C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 5 -haloalkynyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy, C 2 -C 8 -alkynyl, C8 alkenyloxy, C 2 -C 8 haloalkenyloxy, C 2 -C 8 alkynyloxy, C 2 -C 8 haloalkynyloxy, Cs-Cs
• Cycloalkyl C3-Cs-halocycloalkyl, C3-Cs-cycloalkoxy or C3-Cs-halocycloalkoxy;
• a 4 are independently hydrogen, Ci-Cs-alkyl, Ci-C 8 -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl,
• R L is halogen, cyano, nitro, Ci-C8 -alkyl, C 8 haloalkyl, C 8 - alkoxy, Ci-C8-haloalkoxy, C3-C8 cycloalkyl, C3-C 8 -Halogencyclo - alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkoxy, C3-C 8 -Halogencyclo- alkoxy, Ci-C8-alkylcarbonyl, Ci-Cs-alkylcarbonyloxy, Ci-C 8 - alkoxycarbonyl, amino, Ci C 8 alkylamino, di-C 1 -C 8 alkylamino;
• L is halogen, cyano, nitro, cyanato (OCN), C 8 -alkyl, C 8 -HaIo- genalkyl, phenyl-Ci-C ⁇ -alkyloxy, C2-C8 alkenyl, C2-C8 haloalkenyl , C2-C8 alkynyl, C2-C8 haloalkynyl, C4-Cio-alkadienyl, C4-Cio-alkadienyl halogen, Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyloxy, d- C 8 alkylsulfonyloxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C2-C 8 - alkynyloxy, C2-C8 haloalkynyloxy, C3-C8 cycloalkyl, Cs-C 8 -
• n 0, 1 or 2;
• a 1 is hydrogen, hydroxy, Ci-C 8 alkyl, Ci-C8-haloalkyl, amino, Ci-C8-alkylamino or di-Ci-C 8 alkylamino,
• a 2 is one of the groups mentioned at A 1 or C 2 -C 8 -alkenyl, C 2 -C 8 -
• a 3, A 4 are independently hydrogen, Ci-C 8 alkyl, Ci-C 8 -HaIo- genalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C3-C8 cycloalkyl, C3-C 8 -Halogencyclo- alkyl, C3-C8 cycloalkenyl, or C3-C8 halocycloalkenyl; where the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups R L :
• R L is halogen, cyano, nitro, Ci-C8 -alkyl, C 8 haloalkyl, C 8 -
• Ci-C8-haloalkoxy C3-C8 cycloalkyl, C3-C 8 -Halogencyclo- alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkoxy, C3-C 8 -Halogencyclo- alkoxy, Ci- C 8 alkylcarbonyl, Ci-C8-alkylcarbonyloxy, Ci-C 8 - alkoxycarbonyl, amino, Ci-C8-alkylamino, di-Ci-C 8 alkylamino;
• R is hydrogen, Ci-C 8 alkyl-Al, C 8 haloalkyl, C 2 -C 8 alkenyl,
• R 3 is Ci-C 8 alkyl, Ci-C8-haloalkyl, Ci-C8-alkoxy, Ci-C 8 - represents halogenoalkoxy or NA 3 A 4;
• R 4 is C 1 -C 8 -alkyl, phenyl-C 1 -C 8 -alkyl or phenyl, wherein the
• Each phenyl group is unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
• R 1 , R 2 independently of one another are C 1 -C 6 -alkyl, C 1 -C 8 -haloalkyl, Cr
• R 5 is H or C 1 -C 8 -alkyl and R 6 is C 1 -C 8 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl or R 5 and R 6 together represent an alkylene chain having four or five C atoms or form a radical of the formula -CH 2 -CH 2 -O-CH 2 -CH 2 - or -CH 2 -CH 2 -NR 7 -CH 2 -CH 2 -, wherein R 7 is hydrogen or C 1 -C 4 -alkyl; where the aromatic
• Groups in the aforementioned radicals are each independently unsubstituted or substituted by one, two or three groups selected from halogen and C 1 -C 4 -alkyl; or a group SM, where M means:
• M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E) Z 2
• Z 1 and Z 2 are independently hydrogen or C 1 -C 8 alkyl
• Z 3 and Z 4 are independently hydrogen, C 1 -C 8 -alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl; and their agriculturally acceptable salts.
• the present invention relates to compounds of the formula I in which the variables have the following meanings:
• B is phenyl which is unsubstituted or substituted by one, two, three or four identical or different substituents L, where L is
• L is halogen, cyano, nitro, cyanato (OCN), C 8 alkyl-Al, CrC 8 -HaIo- genalkyl, phenyl-CrC ⁇ -alkyloxy, C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 haloalkenyl, C 2 - C 1 -alkynyl, C 2 -C 8 -haloalkynyl, C 4 -C 10 -alkadienyl, C 1 -C 10 -haloalkadienyl, C 1 -C 8 -alkoxy, C 1 -C -haloalkoxy, C 1 -C 8 -alkylcarbonyloxy, C 1 -C 5 -alkylsulfonyloxy, C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C2-C8-
• n 0, 1 or 2;
• a 1 is hydrogen, hydroxy, C 1 -C 8 -alkyl, C 1 -C 5 -haloalkyl, amino, C 1 -C 6 -alkylamino or di-C 1 -C 5 -alkylamino,
• a 2 is one of the groups mentioned at A 1 or C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -haloalkynyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy , C 2 -C 8 alkenyloxy, C 2 -C 8 haloalkenyloxy, C 2 -C 8 alkynyloxy, C 2 -C 8 haloalkynyloxy, C 1 -C 8 cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 8 -cycloalkoxy or C 3 -C 8 -halocycloalkoxy ;
• a 3 , A 4 independently of one another are hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 5 -alkenyl, C 2 -C 5 -haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 5 -haloalkynyl, C 2 -C 5 -alkyl Cs-cycloalkyl, C3-Cs-halogenocycloalkyl, C3-Cs-cycloalkenyl or Cs-Cs-halocycloalkenyl;
• R L is halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -
• Ci-Cs-haloalkoxy Cs-Cs-cycloalkyl, C3-Cs-Halogencyclo-alkyl, C3-Cs-cycloalkenyl, Cs-Cs-cycloalkoxy, C3-Cs-halogenocycloalkoxy, Ci-Cs-alkylcarbonyl, ci C 1 -C 4 -alkylcarbonyloxy, C 1 -C 8 -alkoxycarbonyl, amino, C 1 -C 8 -alkylamino, C 1 -C -alkylamino;
• R 3 is Ci-C 8 alkyl, Ci-C8-haloalkyl, Ci-C8-alkoxy, Ci-C 8 -
• R 4 is Ci-C ⁇ -alkyl, phenyl-Ci-C 8 -alkyl or phenyl, wherein the
• Each phenyl group is unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl;
• R 1, R 2 independently of one another Ci-C 8 alkyl, Ci-C8-haloalkyl, d-Cs-alkoxy, Ci-C8-alkoxy-Ci-C 8 alkoxy, Ci-C8-haloalkoxy, Ci- C 8 -
• M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E) Z 2
• Z 1 and Z 2 are independently hydrogen or Ci-Cs-alkyl
• Z 3 and Z 4 are independently hydrogen, C 1 -C 8 alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl; and their agriculturally acceptable salts.
• B is phenyl which is unsubstituted or substituted by one, two or three substituents independently selected from halogen, NO 2, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 haloalkyl, Ci-C4 haloalkoxy, Cr C4 alkylamino, Ci-C 4 dialkylamino, thio, and Ci-C 4 alkylthio.
• D is a group SR, where R is hydrogen (compounds 1-1).
• D is a group SR, where R is C 1 -C 4 -alkyl, in particular methyl or ethyl, preferably methyl.
• R 3 is hydrogen.
• R 3 is C 1 -C 4 -alkyl, in particular methyl or ethyl, preferably methyl.
• R 3 is C 1 -C 4 -haloalkyl, especially trifluoromethyl.
• R 3 is C 1 -C 4 alkoxy, especially methoxy or ethoxy.
• R 3 is methylamino, dimethylamino, ethylamino, diethylamino or phenylamino.
• D is a group SR, where R is CN.
• D is a group SR, where R is SO 2 R 4 and R 4 is C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl, where the phenyl groups are each unsubstituted or are substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl.
• D is a group SM, wherein M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E )
• Z 3 and Z 4 are independently hydrogen, C 1 -C 4 -alkyl, benzyl or phenyl.
• M represents Na, 1 ⁇ 2Cu, 3Fe, HN (CHs) 3 , HN (C 2 Hs) 3 , N (CHs) 4 or H 2 N (C 3 HT) 2 , in particular Na, 1/2 Cu, HN (CH 3 ) 3 or HN (C 2 Hs) 3 , especially Na, 1/2 Cu, HN (CH 3 ) 3 or HN (C 2 Hs) 3 .
• D is a group D 1 (compounds I-2), where A and B are independently defined or preferably defined herein:
• Dl I-2 Preferably both A and B have the same meaning in compounds I-2.
• D is a group Dil, where # is the point of attachment to the triazolyl ring and Q, R 1 and R 2 are as defined herein or preferably defined:
• Table 1 1a Compounds I, wherein A is 3-fluoro-4-chlorophenyl and the combination of B and D corresponds in each case to one row of Table A (compounds 1.1 1aA-1 to l.1 1 aA-2295 ) Table 12a
• Table 19a shows compounds I in which A is 2-methyl-5-fluorophenyl and the combination of
• Table 40a shows compounds I in which A is 2-methoxy-6-fluorophenyl and the combination of
• Table 58a Compounds I in which A is 2- (trifluoromethoxy) -3-fluorophenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds 1.58aA-1 to 1.58aA-2295) Table 59a
• Table 61a Compounds I in which A is 2- (trifluoromethoxy) -6-fluorophenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds 1.61 aA-1 to 1.61aA-2295)
• Table 66a Compounds I in which A is 2-fluoro-5- (trifluoromethoxy) phenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds I.66aA-1 to I.66aA-2295)
• Table 74a Compounds I in which A is 2-fluoro-3- (difluoromethoxy) phenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds I.74aA-1 to I.74aA-2295)
• Table 79a Compounds I in which A is 2- (trifluoromethylthio) -4-fluorophenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds I.79aA-1 to I.179aA-2295) Table 80a
• Table 82a Compounds I in which A is 3- (trifluoromethylthio) -4-fluorophenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds I.82aA-1 to I.82aA-2295)
• Table 87a Compounds I, wherein A is 3-fluoro-4- (trifluoromethylthio) phenyl and the combination of B and D corresponds in each case to one row of Table A (Compounds I.87aA-1 to 1.87aA-2295)
• Line of Table B corresponds (compounds l-2.2bB-1 to l-2.2bB-255)
• Table C corresponds (compounds N.3cC-1 to N.3cC-234)
• Table 8c Compounds II, wherein A is 2-fluoro-4-chlorophenyl and B corresponds in each case to one row of Table C (Compounds II.8cC-1 to II.8cC-234)
• Table 27c Compounds II, wherein A is 2-ethyl-3-fluorophenyl and B corresponds in each case to one row of Table B (Compounds N.27cB-1 to N.27cB-255)
• Table 36c Compounds II, wherein A is 3-fluoro-4-ethylphenyl and B corresponds in each case to one row of Table B (Compounds N.36cB-1 to N.36cB-255)
• Table 51d Compounds III, wherein A is 2- (trifluoromethyl) -6-fluorophenyl and the combination of B and Z corresponds in each case to one line of Table D (compounds IN.51dD-1 to III.51dD-1275) Table 52d
• Table 54d Compounds III, wherein A is 2-fluoro-3- (trifluoromethyl) phenyl and the combination of B and Z corresponds in each case to one row of Table D (Compounds IM.54dD-1 to IM.54dD-1275)
• Table 72d Compounds III, wherein A is 3- (difluoromethoxy) -4-fluorophenyl and the combination of B and Z corresponds in each case to one row of Table D (Compounds IM.72dD-1 to IN.72dD-1275) Table 73d
• the compounds IIIa, INb, INc and IIId-1 compiled in the following Tables 1e to 93e, Tables 1f to 93f, Tables 1g to 93g and Tables 1h to 93h are preferred.
• the groups mentioned in the tables for a substituent are also considered individually, regardless of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.
• Table B corresponds (compounds Nla.4eB-1 to Nla.4eB-255) Table 5e
• Table 16e compounds IIIa where A is 3-chloro-4-fluorophenyl and B corresponds in each case to one row of Table B (compounds IIIa.16eB-1 to IIIa.16eB-255)
• Table 21e compounds IIIa where A is 3-methyl-4-fluorophenyl and B corresponds in each case to one row of Table B (Compounds Nla.21 eB-1 to Nla.21eB-255)
• Table 3Oe compounds IIIa where A is 2-ethyl-6-fluorophenyl and B corresponds in each case to one row of Table B (Compounds Nla.30eB-1 to Nla.30eB-255)
• Table 35e compounds IIIa in which A is 2-fluoro-5-ethylphenyl and B corresponds in each case to one row of Table B (Compounds Nla.35eB-1 to Nla.35eB-255)
• Line of Table B corresponds (compounds Nla.39eB-1 to Nla.39eB-255)
• Line of Table B corresponds (compounds Nla.44eB-1 to Nla.44eB-255)
• Table 53e compounds IIIa in which A is 3- (trifluoromethyl) -5-fluorophenyl and B corresponds in each case to one row of Table B (compounds Nla.53eB-1 to Nla.53eB-255)

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• 2008
  • 2008-12-12 CN CN2008801270104A patent/CN101945580A/zh active Pending
  • 2008-12-12 WO PCT/EP2008/067394 patent/WO2009077443A2/de active Application Filing
  • 2008-12-12 BR BRPI0821296-1A2A patent/BRPI0821296A2/pt not_active IP Right Cessation
  • 2008-12-12 AU AU2008337565A patent/AU2008337565A1/en not_active Abandoned
  • 2008-12-12 CA CA2707615A patent/CA2707615A1/en not_active Abandoned
  • 2008-12-12 EP EP08862202A patent/EP2234488A2/de not_active Withdrawn
  • 2008-12-12 EA EA201000950A patent/EA201000950A1/ru unknown
  • 2008-12-12 JP JP2010538602A patent/JP2011506539A/ja active Pending
  • 2008-12-12 MX MX2010006143A patent/MX2010006143A/es not_active Application Discontinuation
  • 2008-12-12 KR KR1020107015918A patent/KR20100093127A/ko not_active Application Discontinuation
  • 2008-12-12 US US12/808,793 patent/US20100317515A1/en not_active Abandoned
  • 2008-12-12 NZ NZ585915A patent/NZ585915A/en not_active IP Right Cessation
  • 2008-12-18 AR ARP080105547A patent/AR069834A1/es not_active Application Discontinuation
  • 2008-12-19 TW TW097149895A patent/TW200930299A/zh unknown
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• 2010
  • 2010-06-01 IL IL206127A patent/IL206127A0/en unknown
  • 2010-06-29 CR CR11548A patent/CR11548A/es not_active Application Discontinuation
  • 2010-07-09 MA MA33005A patent/MA32007B1/fr unknown
  • 2010-07-15 EC EC2010010344A patent/ECSP10010344A/es unknown

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