JPH08511772A - Arylacetamides, processes for their preparation, compositions containing them and their use as fungicides - Google Patents

Abstract

(57) [Summary] Formula I [Wherein A is an optionally substituted aryl group; A'is an optionally substituted aryl group; B is a carbonyl group or a methylene group, which is optionally substituted hydroxy and optionally further X is an optionally substituted alkylene chain having from 2 to 4 carbon atoms, where any two substituents on any carbon are oxo or And R ⁷ is heterocyclyl, aryl, silyl, alkyl, alkenyl, cycloalkyl, alkynyl, cycloalkenyl, amino, hydroxy, mercapto, each of which is Optionally substituted), hydrogen, cyano or acyl, wherein B is optionally substituted hydroxy. Any other compound represented by any one and may form a ring together] substituents on conversion by the substituents on the hydroxy when are R ⁷ or B, in particular It has fungicidal activity against phytopathogenic fungi.

Description

Detailed Description of the Invention         Aryl acetamides, their production method, and their         Compositions containing and their use as fungicides   The present invention relates to arylacetamides, methods for producing them, and compositions containing them. And their use as fungicides.   Substituted arylacetate having an optionally substituted hydroxy group attached at the α-position. Toamide is used as an active ingredient of herbicides (JP-5 8032-853) and for the treatment of skin diseases. It is described as a composition (EP-A-98743). Also, in the chemical literature as an intermediate There are many reference descriptions for all such compounds.   Surprisingly, new allies exhibit beneficial activity in combating fungi, especially phytopathogenic fungi. Luacetamide was found.   That is, the present invention provides a formula I for eradication of fungi. [In the formula,   A is an optionally substituted aryl group;   A'is an optionally substituted aryl group;   B is a carbonyl or methylene group (which may be optionally substituted hydroxy) And substituted by any further substituents);   X is an optionally substituted alkylene chain having 2 to 4 carbon atoms (wherein Any two substituents on either carbon are oxo or optionally substituted i Can form a mino group) R; and   R⁷Is heterocyclyl, aryl, silyl, alkyl, alkenyl, cycloal Rualkyl, alkynyl, cycloalkenyl, amino, hydroxy, mercapto Each of which is optionally substituted), hydrogen, cyano or acyl Where B is substituted with an optionally substituted hydroxy, The substituent on the hydroxy is R⁷Or with any of the other substituents on B To form a ring], its stereoisomers and Relates to the use of those mixtures.   Many of the compounds of formula I are new and therefore the present invention is directed to all such novel compounds. Especially in formula I   X and R⁷Has the above definition;   B is a methylene group (which is substituted by an optionally substituted hydroxy) Is);   A'is dialkoxyphenyl (wherein the phenyl group is optionally further substituted Is); and   A is halo, cyano, nitro, optionally substituted amino, optionally substituted Selected from selected alkyl, haloalkoxy, aryl, heterocyclyl. Phenyl substituted with one or more groups, where the phenyl group is optionally further substituted Are included); including compounds.   For these novel compounds, A is halo, cyano, alkyl, trifluoromethyl Preferred is phenyl substituted with one or more groups selected from aryl and haloalkoxy. Good. It is especially preferred that the substituent is at the 4-position.   A'is 3,4-dimethoxyphenyl or 4-ethoxy-3-methoxyphenyl Preferably.   The invention also relates to the melting point or like oils, gums, waxes or foams. All the compounds in the table below, which are described in physical description, are included as novel compounds.   In the above, the alkyl moiety and the alkyl moiety of the alkyl-containing group are 1 to 20 It is preferably composed of 1 to 6 carbon atoms. Alkenyl and alkynyl groups are It generally consists of 3 to 6 carbon atoms. Cycloalkyl or cycloalkene Preferably, the radical comprises 3 to 8 carbon atoms.   Any alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl Halo is an example of a substituent when present on a alkoxy, alkyl or alkylthio group. Gen, cyano, alkoxy (for example consisting of 1 to 4 carbon atoms, for example Optionally substituted by halo), hydroxy, alkylthio, nitro, optionally Substituted amino, carboxy, alkoxycarbonyl, acyl, acyloxy, Mention may be made of heterocyclyl and aryl.   Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl .   The aryl group is phenyl, and when optionally substituted, the substituent is, for example, Halogen, optionally substituted alkyl or alkoxy, aryl, het Rocyclyl, aryloxy, cyano, nitro, optionally substituted amino Or acyl, or the two adjacent groups are as described above for aryl. Fused benzo groups, which are optionally substituted, can be formed. Any ally Le Preferred substituents on the group are halogen, alkyl, trifluoromethyl, alkoxy , Haloalkoxy, nitro, dialkylamino, amino or cyano.   Hydroxy and mercapto groups are, for example, optionally substituted alkyl, Cycloalkyl, aryl, acyl, cyano and heterocycle substituted by It may be substituted with a series of groups such as Kuryl.   In the case where B is a hydroxy-substituted methylene group, any additional group on B Examples of the substituents include a substituent which can be any substituent on hydroxy. Can be   The term heterocyclyl includes both aromatic and non-aromatic heterocyclic groups. It Heterocyclyl groups are up to three heterocyclic groups selected from nitrogen, oxygen and sulfur. It is a generally 5- or 6-membered ring containing a b atom. These heteropsies The curyl group can be fused to the benzene ring to form a fused heterocyclic group. Hete Examples of rocyclyl groups include thienyl, furyl, pyridyl, pyrimidinyl, pyra. Zolyl, thiazolyl, thiazolinyl, oxazolyl, benzimidazolyl, tet Razolyl, benzoxazolyl, thiadiazolyl, dioxolanyl, imidazopi Lysinyl, 1,3-benzoxazinyl, 1,3-benzothiazinyl, oxazolopyri Dinyl, triazolyl, triazinyl, imidazolyl, morpholino, benzofura Nyl, pyrazolinyl, quinolinyl, quinazolinyl, sulforanyl, dihydroquina Zolinyl, benzothiazolyl, piperidinyl, phthalimide, 2-oxopyrroli There are dino, 2-oxobenzoxazolin-3-yl and benzofuranyl. The heterocyclyl group may itself be substituted as described above for phenyl, for example. sell.   Amino groups are for example one or two optionally substituted alkyl or acyl groups. Substituted with two or two substituents may be substituted with other heteroatoms. A ring which may also contain preferably 5 to 7-membered rings such as morpholine, thiomol Holins or piperidines can be formed.   The term acyl includes residues of sulfur-containing and phosphorus-containing acids and carboxylic acids. It That is, an example of an acyl group is -COR^a, -COOR^a, -CO-Am, -CS-Am, -COSR^a,- CSSR^a, -S (O)_qR^a, -S (O)_qOR^a, -S (O)_qAm, -P (= O) (OR^a) (OR^b), -P (= S) (OR^a) (OR^b) And-CO-COOR^a(Where R^aAnd R^bAre the same or different and are hydrogen, An alkyl substituted by, an optionally substituted cycloalkyl, optionally Substituted cycloalkenyl, optionally substituted alkenyl, optionally A substituted alkynyl, aryl or heterocyclyl, where Am is optionally Substituted amino and q is 1 or 2).   In the above preferred compounds and salts thereof, particularly acid addition salts,   A is of formula II or III Is a group represented by   A'is of formula IV or V A group represented by the following formula;   m, n, m'and n'are integers;   m = 1-5;   n = 1 to 7;   m '= 0-5;   n '= 0-7;   R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₈ ) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁~ C₆)- Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Alkyl, (C₁ ~ C₈) -Heteroaryl, (C₁~ C₈) -Non-aromatic heterocyclyl, (C₁~ C₈) -Hetero Aryl- (C₁~ C₆) -Alkyl, (C₁~ C₈) -Non-aromatic heterocyclyl- (C₁~ C₆)- Alkyl, cyano, nitro, halogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCO R³, -OCOOR³, -OCO-NR³R^Four, -SR³, -SOR³, -SO₂R³, -SO₂-OR³, -SO₂NR³R^Four, -NR³R^Four , -NR³-SO₂R^Four, -NR³-COR^Four, -P (O) (OR³) (OR^Four), -O-P (O) (OR³) (OR^Four) Or-SiR³ ₃ And   In the first 10 of these groups, optionally the following conditions:   a) If 1, 2 or 3 CH-CH- units are present in a non-cyclic state, Each is replaced by 1, 2 or 3 CH = CH-units,   b) 1 CH₂-CH₂-If the unit exists in a non-cyclic state, it is C≡C- Replaced by units,   c) When one CH-CH- unit is present in a ring, it is a C≡C- unit Replaced by,   d) Hydrogen atoms present on carbon atoms which are not part of the ring are cyano, nitro or halo. Gen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O-CO-NR³R^Four, -SR³ , -SOR³, -SO₂R³, -SO₂-OR³, -SO₂-NR³R^Four, -NR³R^Four, -NR³-COR^Four, -P (O) (OR³) (OR^Four ), -O-P (O) (OR³) (OR^Four) And -SiR³ ₃Up to three identical or phases selected from the group Replaced by a different substituent,   e) After substitution by d), hydrogen atoms remaining on carbon atoms not part of the ring Partially or wholly replaced by one or different halogen atoms,   f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Where hydrogen is Up to three identical or different substituents selected from the substituents described in d) and d). Is replaced by a substituent,   g) after substitution by f) the hydrogen atoms remaining on a carbon atom which is part of the ring are identical Or partially or totally replaced by different halogen atoms,   h) 1 or 2 CHs present other than at the bonding position of the group₂-Unit is O, S , CO and NR³Replaced by the same or different groups selected from the group , At least one of is satisfied;   R³And R^FourAre the same or different and independent of each other, hydrogen, (C₁ ~ C₁₈) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁ ~ C₆) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Alkyl , (C₁~ C₈) -Heteroaryl or (C₁~ C₈) -Heteroaryl- (C₁~ C₆)- Alkyl, where the first 7 groups optionally have the following conditions:   a) If 1, 2 or 3 CH-CH- units are present in a non-cyclic state, Each is replaced by 1, 2 or 3 CH = CH-units,   b) 1 CH₂-CH₂-If the unit exists in a non-cyclic state, it is C≡C- Replaced by units,   c) When one CH-CH- unit is present in a ring, it is replaced by a C = C- unit available,   d) Hydrogen atoms present on carbon atoms which are not part of the ring are cyano, nitro or halo. Gen, -COR³′, -COOR³′, -CONR³′₂, -OR³′, -OCOR³′, -OCOOR³′, -O-CO-N R³′, -SR³′, -SOR³′, -SO₂R³′, -SO₂-OR³′, -SO₂NR³′₂, -NR³′₂, -NR³′ -COR³′, -P (O) (OR³) (OR^Four), -O-P (O) (OR³) (OR^Four) And -SiR³′₃Selected from a group of Replaced by up to three identical or different substituents,   e) After substitution by d), hydrogen atoms remaining on carbon atoms not part of the ring Partially or wholly replaced by one or different halogen atoms,   f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³′ (R³′ = Hydrogen Up to three identical or phases selected from the substituents described in d) and d) Replaced by a different substituent,   g) after substitution by f) the hydrogen atoms remaining on a carbon atom which is part of the ring are identical Or partially or totally replaced by different halogen atoms,   h) 1 or 2 CHs present other than at the bonding position of the group₂ -Units are O, S, CO and NR³By the same or different groups selected from the group ' Will be replaced, At least one of:   R³And R^FourTogether (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is CO-, O, S or NR depending on the combination³Replaced by '));   R³′ Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Arkini Le, (C₁~ C₆) -Haloalkyl, (C₂~ C₆) -Haloalkenyl, (C₂~ C₆) -Halo Archi Nil, (C₃~ C₆) -Cycloalkyl, (C₃~ C₆) -Cycloalkyl- (C₁~ C_Four) -Alkyl , (C₆~ C_Ten) -Aryl, (C₇~ C₁₁) -Aralkyl and (C₁~ C_Five) -Heteroaryl The same or different groups selected from the group Is cyano, nitro, halogen, (C₁~ C_Four) -Alkyl, (C₁~ C_Four) -Haloalkyl, (C₁ ~ C_Four) -Alkoxy, (C₁~ C_Four) -Haloalkoxy, phenyl, phenoxy, benzyl 1 or 2 identical or different selected from the group Substituents can be present in the ring;   B is of formula VI or VII Is the basis of;   R^FiveIs hydrogen, (C₁~ C₁₈) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Siku Lower alkyl- (C₁~ C₆) -Alkyl, (C₆~ C₁₈)- Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Alkyl, (C₁~ C₈) -Heteroaryl , (C₁~ C₈) -Heteroaryl- (C₁~ C₆) -Alkyl, cyano, -COR³, -COOR³, -CON R³R^FourOr-SiR³ ₃(Where R³And R^FourHas the above definition), where In the groups described in the 2nd to 8th positions, R¹And R²Conditions specified for the group At least one of ~ h) is satisfied;   R⁶Is hydrogen or R¹With the definition given above for R^Five= Hydrogen R if⁶Is not bonded through an O-, S- or N-atom, or   R^FiveAnd R⁶Together (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is CO , O, S or NR³C optionally substituted and / or present with ' One of the H-CH- units forms a C = C- unit, optionally substituted);   R⁷Is hydrogen, or R above except for nitro and halogen.¹Definitions in Have; or   R^FiveAnd R⁷Together (C₂~ C_Five) -Alkylene group (where 1 CH₂-The base is CO , O, S or NR³C optionally substituted and / or present with ' One of the H-CH-units is optionally replaced with a C = C-unit) and R⁶ Has the above definition;   R⁶And R⁷Together (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is CO , O, S or NR³C optionally substituted and / or present with ' One of the H-CH-units is optionally replaced with a C = C-unit) and R^Five Has the above definition;   X is the formula VIII             -CR⁸R⁹-(CR^TenR¹¹)_p-(VIII) Is the basis of;   R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , R⁷Has the definition described above for or is halogen or nitro, And here R⁸And R⁹Or R^TenAnd R¹¹Together again form an oxo group Can also be O by   R^TenAnd R¹¹Group together = N-OR³Can be formed, or   R⁷And R⁸Together (C₂~ C_Five) -Forming an alkylene group, R⁷And R^TenIs one It becomes a cord (C₁~ C_Four) -Forming an alkylene group or R⁸And R^TenAre together (C₃~ C₆) -Alkylene groups are formed, in which in each case one CH₂-Group is CO, O , S or NR³CH-CH optionally replaced by and / or present -One of the units is optionally replaced by a C = C-unit and Unrelated groups have the above definitions; and   p is 1, 2 or 3.   Preferred compounds of formula I are:   R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁~ C_Four)- Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁~ C_Four) -Alkyl, (C₁ ~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C_Four) -Alkyl, cyano , Nitro, halogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -OCO -NR³R^Four, -SR³, -SOR³, -SO₂R³, -SO₂-OR³, -SO₂NR³R^Four, -NR³R^Four, -NR³-SO₂R^Four, -N R³-COR^FourOr-SiR³ ₃And Here, for the first seven groups, optionally the above-mentioned conditions defined for these groups B), c), e), g) and h) and the following conditions:   a) When one CH-CH- unit is present in a non-cyclic state, it is one CH = CH-replaced by units,   d) Hydrogen atoms present on carbon atoms which are not part of the ring are cyano, nitro or halo. Gen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O-CO-NR³R^Four, -SR³ , -SOR³, -SO₂R³, -SO₂-OR³, -SO₂-NR³R^Four, -NR³R^Four, -NR³-COR^FourAnd-SiR³ ₃Flock of Replaced by up to 3 identical or different substituents selected from   f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Where hydrogen is Up to three identical or different substituents selected from the substituents described in d) and d). Is replaced by a substituent, At least one of the   R³And R^FourAre the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₃~ C₈) -Cycloalkyl, (C₃~ C₈) -Cycloalkyl- (C₁~ C_Four) -A Luquil, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁~ C_Four) -Alkyl, (C₁~ C₈ ) -Heteroaryl or (C₁~ C₈) -Heteroaryl- (C₁~ C_Four) -Alkyl, In the last seven groups mentioned here, the abovementioned groups defined for these groups are sometimes used. Conditions b), c), e), g) and h) and the following conditions:   a) When one CH-CH- unit is present in a non-cyclic state, it is one CH = CH-replaced by units,   d) Hydrogen atoms present on carbon atoms which are not part of the ring are cyano, nitro or halo. Gen, -COR³′, -COOR³′, -CONR³′₂, -OR³′, -OCOR³′, -OCOOR³′, -O-CO-NR³′, -SR³′, -SOR³′, -SO₂R³′, -SO₂-OR³′, -SO₂NR³′₂ , -NR³′₂, -NR³′ -COR³′ And -Si (R³′)₃Up to 3 of the same selected from the group Replaced by one or different substituents,   f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³′ (R³′ = Hydrogen Up to three identical or phases selected from the substituents described in d) and d) Replaced by a different substituent, At least one of is satisfied;   R³'And B have the above definitions;   R^FiveIs hydrogen, (C₁~ C₁₂) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Siku Lower alkyl- (C₁~ C_Four) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁ ~ C_Four) -Alkyl, (C₁~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C_Four ) -Alkyl, cyano, -COR³, -COOR³, -CONR³R^FourOr SiR³ ₃(Where R³And R^Four Have the definitions given above), where in the radicals 2-8 described below, Than R¹And R²At least one of the conditions a) to h) specified for the group L;   R⁶Is hydrogen or R¹With the definition given above for R^Five= Hydrogen R if⁶Is not bonded through an O-, S- or N-atom, or   R^FiveAnd R⁶Forms a ring as defined above;   R⁷Is hydrogen, or R above except for nitro and halogen.¹Definitions in Have; or   R^FiveAnd R⁷Forms a ring as defined above;   R⁶And R⁷Forms a ring as defined above;   X has the above definition;   R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , R⁷Has the definition described above for or is halogen, and wherein R⁸Oh And R⁹Or R^TenAnd R¹¹Are also grouped together to form an oxo group. Can be O, or   R^TenAnd R¹¹Group together = N-OR³Can be formed, or   R⁷And R⁸, R⁷And R^TenOr R⁸And R^TenForms a ring as defined above;   And the groups not related to this ring bond have the above definitions; and   p has the definition given above; The compounds and their salts, especially the acid addition salts.   Particularly preferred compounds and their salts are:   R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₂~ C₁₂) -Alkenyl, (C₂~ C₁₂) -Alkynyl, (C₆~ C₁₂) -Ally Le, (C₇~ C₁₃) -Aralkyl, (C₁~ C₁₂) -Alkoxy, (C₂~ C₁₂) -Alkenylo Kish, (C₂~ C₁₂) -Alkynyloxy, (C₁~ C₁₂) -Alkylthio, (C₆~ C₁₂) -Ant Oxy, (C₇~ C₁₃) -Arylalkoxy, (C₇~ C₁₃) -Arylalkylthio , (C₆~ C₁₂) -Arylthio, heteroaryl, heteroaryl- (C₁~ C_Four) -Archi , Heteroaryloxy, heteroaryl- (C₁~ C_Four) -Alkyloxy, hetero Aryl- (C₁~ C_Four) -Alkylthio, heteroaryloxy- (C₁~ C_Four) -Alkyl ( Wherein the heterocyclic aryl group is each up to 8 carbon atoms and N, Having up to 4 identical or different heteroatoms selected from S and O) , (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkoxy, (C₃~ C₁₂)_-Cyclo Alkenyl, (C₃~ C₁₂) -Cycloalkenyloxy, -CN, OH, NO₂, F, Cl, Br, I, -COOR³, -COR³, -OCOR³, -CONR³R^Four, -R³COR^Four, -NR³R^Four, -SO₂NR³R^Four, -NR³SO₂ R^Four, -NR³COR^Four, -SiR³ ₃, -SO₂R³Or-SO₃R³Where the first 23 groups are Optionally replaced in the manner described above,   R³And R^FourHas the above definition;   R^FiveAnd R⁶Are independent of each other, hydrogen, (C₁~ C₁₂) -Alkyl, (C₂~ C₁₂) -A Lucenyl, (C₂~ C₁₂) -Alkynyl, (C₆~ C₁₂) -Aryl, (C₇~ C₁₂) -Aralkyl , (C₇~ C₁₂) -Aryloxyalkyl, heteroaryl, heteroaryl- (C₁~ C_Four) -Alkyl, heteroaryloxy- (C₁~ C_Four) -Alkyl (where heterocyclic ant Up to 8 carbon atoms each and 4 selected from N, S and O Up to the same or different heteroatoms), (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkenyl, COOR³, COR³, -CONR³R^FourOr-SiR³ ₃And Where the 2nd to 12th groups are optionally substituted as defined above, Or R^FiveIs R⁶Saturated or unsaturated 5-, 6-, 7- or 8-membered together with Can form a ring, and R³And R^FourHas the above definition, and R^FiveBut water R if not prime⁶Is also (C₁~ C₆) -Alkoxy, (C₁~ C₆) -Haloalkoxy, fu Enoxy, CN, -NR³R^Four, NR³SO₂R^FourOr-NR³COR^FourCan also be;   R⁷Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Alkynyl , (C₆~ C₁₂) -Aryl, (C₇~ C₁₂) -Alkal, (C₁~ C₆) -Alkoxy, (C₂~ C₆) -Alkenyloxy, (C₃~ C₆) -Alkynyloki Si, (C₆~ C₁₂) -Aryloxy, (C₇~ C₁₃) -Alkaryloxy, heteroaryl , Heteroaryl- (C₁~ C_Four) -Alkyl, heteroaryloxy, heteroaryl -(C₁~ C_Four) -Alkyloxy (wherein the heteroaryl group is up to 8 carbons each Elementary atoms and up to four identical or different heters selected from N, S and O B), (C₃~ C₈) -Cycloalkyl, (C₃~ C₈) -Cycloalkoxy, (C₃ ~ C₈) -Cycloalkenyl, (C₃~ C₈) -Cycloalkenyloxy, -OH, COOR³, CO R³, -OCOR³, CONR³R^Four, NR³COR^Four, SiR³ ₃Or NR³R^FourAnd here is the second to The 19th group is optionally substituted as defined above, and R³Oh And R^FourHas the above definition, or R⁷Is R^FiveOr R⁶Saturated or unsatisfied with Forming part of a saturated 5- or 6-membered ring;   R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , F, Cl, Br, I, CN or R⁷Has the above definition for R, or R⁷ And R⁸, R⁷And R^TenOr R⁸And R^TenIs saturated or unsaturated 5- or 6- , 7- or 8-membered ring, and the remaining groups and variables are as defined above. And a salt thereof.   Particularly preferred compounds and their salts are:   R¹And R²Are the same or different and independent of each other, and (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃~ C₇) -Cycloal Kill, (C₃~ C₇) -Cycloalkenyl, (C₃~ C₆) -Alkoxy, benzyloxy, (C₁ ~ C₆) -Alkylthio, phenyl, phenoxy, phenylthio, (C₂~ C₆) -Arque D Roxy, (C₃~ C₆) -Alkynyloxy, (C₇~ C₁₃) -Phenylalkoxy, (C₇~ C₁₃) -Phenylalkylthio, (C₁~ C₆) -Haloalkyl, (C₁~ C₆) -Halo arcoki Si, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyloxy, especially Luoroalkyl and fluoroalkoxy, (C₃~ C₇) -Cycloalkyloxy, ( C₃~ C₇)_-Cycloalkenyloxy, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆)-Halo Alkenylthio, (C₃~ C₇) -Halocycloalkyl, (C₃~ C₇) -Halocycloalkeni Le, (C₃~_C7) -Halocycloalkoxy, (C₃~ C₇) -Halocycloalkenyloxy, (C₃~ C₇) -Halocycloalkylthio, especially fluoroalkylthio, CN, OH, NO₂, F, Cl, Br, I, CO₂R³, OCOR³, COR³, NR³COR^Four, NR³R^Four, SO₃R³, SO₂NR³R^Four, F Teloaryl, heteroaryloxy (wherein each of the heterocyclic aryl groups is Up to 5 carbon atoms and up to 3 identical or selected from N, S and O Have different heteroatoms), and   R³And R^FourHas the above definition;   m = 1-5;   n = 1 to 4;   m ′ = 2-5;   n '= 2-4;   R^FiveAnd R⁶Are the same or different and independent of each other, hydrogen, (C₁~ C₆)- Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Alkynyl, (C₃~ C₇) -Cycloal Kill, (C₃~ C₇) -Cycloalkenyl, phenyl, heteroaryl (wherein heterocycle The formula aryl groups are each selected from up to 5 carbon atoms and N, S and O Up to 3 Of the same or different heteroatoms), (C₁~ C₆) -Hydroxyalkyl, ( C₁~ C₆) -Haloalkyl, (C₂~ C₆) -Haloalkenyl, COOR³, COR³, CONR³R^FourAlso Is-SiR³ ₃And R^FiveR is not hydrogen⁶Is also (C₁~ C₆) -Alkoxy , Phenoxy, (C₁~ C₆) -Haloalkoxy, CN, NR³R^FourOr NR³COR^FourTo be Can also or R^FiveIs R⁶Together with a saturated or unsaturated 5- or 6-membered ring Can be formed and R³And R^FourHas the above definition,   R⁷Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Alkynyl , Phenyl, (C₁~ C₆) -Alkoxy, phenoxy, (C₂~ C₆) -Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₃~ C₇) -Cycloalkenyloxy, (C₁~ C₆) -Ha Lower alkyl, (C₁~ C₆) -Haloalkoxy, -OH, COOR³, COR³, OCOR³, CONR³R^Four, N R³COR^Four, NR³R^FourOr SiR³ ₃Or R⁷Is R^FiveOr R⁶Become saturated with Or an unsaturated 5- or 6-membered ring is formed, and R³And R^FourHas the above definition Do;   R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other F, Cl, Br, I, CN or R⁷Has the above definition for R, or R⁷Oh And R⁸, R⁷And R^TenOr R⁸And R^TenIs saturated or unsaturated 5- or 6- Can be a member of a member ring, and the remaining groups and variables of are defined above. And the salts thereof, especially the acid addition salts.   Even more particularly preferred in formula I   R¹Is (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃~ C₇) -Cycloalkyl, (C₃~ C₇) -Cycloalkenyl, phenyl, (C₁~ C₆) -Haloa Luquil, (C₂~ C₆) -Halo Arche Nil, (C₂~ C₆) -Haloalkynyl, (C₁~ C₆) -Haloalkoxy, (C₂~ C₆) -Haloa Lucenyloxy, (C₃~ C₆) -Haloalkynyloxy, (C₃~ C₇) -Cycloalkylo Kish, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆) -Haloalkenylthio, (C₃~ C₇)- Halocycloalkyl, (C₃~ C₇) -Halocycloalkenyl, (C₃~ C₇) -Halocycloa Lucoxy, (C₃~ C₇) -Halocycloalkenyloxy, (C₃~ C₇) -Halocycloalkyl Lucio, CN, OH, NO₂, F, Cl, Br, I, CO₂R³, OCOR³, COR³, NR³COR^Four, NR³R^Four , SO₃R³, SO₂NR³R^Four, Heteroaryl, (wherein each of the heterocyclic aryl groups Is up to 5 carbon atoms and up to 3 identical or selected from N, S and O Have different heteroatoms), and   R³And R^FourIs a compound as defined above as well as salts thereof, especially acid addition salts,   And in formula I   R¹Is (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃~ C₇) -Cycloalkyl, (C₃~ C₇) -Cycloalkenyl, (C₁~ C₆) -Alkoxy, Ben Ziroxy, (C₁~ C₆) -Alkylthio, phenoxy, phenylthio, (C₂~ C₆) -A Lucenyloxy, (C₃~ C₆) -Alkynyloxy, (C₇~ C₁₃) -Phenylalkoxy , (C₇~ C₁₃) -Phenylalkylthio, (C₁~ C₆) -Haloalkyl, (C₁~ C₆) -Haloa Lucoxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyloxy, (C₃~ C₇) -Cycloalkyloxy, (C₃~ C₇) -Cycloalkenyloxy, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆) -Haloalkenylthio, (C₃~ C₇) -Halocycloal Kill, (C₃~ C₇) -Halocycloalkenyl, (C₃~ C₇) -Halocycloalkoxy Si, (C₃~ C₇) -Halocycloalkenyloxy, (C₃~ C₇) -Halocycloalkylthio , CO₂R³, OCOR³, COR³, NR³COR^Four, NR³R^Four, Heteroaryloxy (where heterocycle Each of the formula aryl groups is selected from up to 5 carbon atoms and N, S and O Up to 3 identical or different heteroatoms), and   R³And R^FourIs a compound as defined above as well as salts thereof, especially acid addition salts. It   Particularly preferred compounds are   A is of formula II (where m is 1 or 2 and R¹Is halogen, (C₁~ C_Four) -Al Kill especially methyl or halo- (C₁~ C_Four) -Alkyl, especially trifluoromethyl, And R¹Is preferably in the 3 and / or 4 position);   B is -CH (OH)-, -CH (O-acyl)-or -CH (O-alkyl);   R⁷Is hydrogen;   X is optionally substituted ethylene; and   A'is the formula IV (where m'is 2 and R²Is (C₁~ C_Four) -Alkoxy, especially methoxy Or ethoxy, preferably in the 3 and 4 positions). . It is especially preferred that B is -CH (OH)-and X is ethylene.   In the description above and below, the term "halogen" refers to fluorine, chlorine, bromine. Or it is understood to be an iodine atom. The term "alkyl" may be straight or branched. Hydrocarbon groups such as methyl, ethyl, propyl, 1-methylethyl, 2-methyl Propyl, 1,1-dimethylethyl, pentyl, 2-methylbutyl, 1,1-dimethyl Propyl, f Xyl, heptyl, octyl, 1,1,3,3-tetramethylbutyl, nonyl, isono It is understood to be nil, decyl, undecyl or dodecyl.   The term "cycloalkyl" which is monocyclic, bicyclic or tricyclic, preferably monocyclic, is exemplified by For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl It is understood to be a butyl or cyclooctyl group.   The term "cycloalkylalkyl" has the meaning previously given for the term "alkyl". Charcoal having and substituted by hydrocarbon radicals as indicated by the term "cycloalkyl" Hydrogen fluoride groups such as cyclohexylmethyl, 2-cyclohexylethyl or 2-cyclohexylmethyl It is understood to be chlorhexyl-2-propyl.   The term "alkoxy" refers to a hydrocarbon having the meaning previously given for the term "alkyl". It is understood to be a base.   The term "alkoxyalkyl" refers to, for example, 1-methoxyethyl, 2-methoxyethyl. Chill, 2-ethoxyethyl, methoxymethyl, ethoxymethyl, 3-methoxypropyl It is understood to be ropyr or 4-butoxybutyl.   The term "haloalkyl" means that one or more hydrogen atoms are halogen atoms as described above. Or substituted by chlorine or fluorine, as previously described in the term "alkyl". Alkyl groups such as CF₃, CF₃CHF₂, CCl₃, CCl₂F, CF₂CF₂CF₃, CF₂CHFCF₃, CH₂ CF₃, (CF₂)₃CF₃, CF₂H, CHF₂, CH₂Cl, CHCl₂Or CCl₃CH₂Is understood to be The terms haloalkenyl, haloalkynyl, etc. are also understood correspondingly to the above. .   The term "haloalkoxy" means that a halogen hydrocarbon residue is a "haloalkoxy". A haloalkoxy group having the meaning given for the term "alkyl", eg OCH₂F, OCHF₂ , OCF₃, OCH₂CF₃, OCH₂CCl₃, OCH (CF₃)₂Or OCF₂CHFCF₃Is understood to be The terms such as haloalkenyloxy and haloalkynyloxy also correspond to the above. Be understood.   The term "aryl" is eg phenyl, naphthyl or biphenyl, especially phenyl. It is understood to be Le.   The term "arylalkyl" has been shown above substituted with an aryl group One of the alkyl groups such as benzyl, 2-phenylethyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 3-phenylpropyl or 4-phenylbutane Understood to be chill,   The term "heteroaryl" means that at least one CH-group is replaced by N. And / or at least two adjacent CH-groups are replaced by S, NH or O It is to be understood that it is an aryl group having the above definition which is replaced. Such a group Examples of are thienyl, furyl, benzofuryl, pyrrolyl, imidazolyl, pyra. Zolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, oxazolyl, There are isoxazolyl, thiazolyl, isothiazolyl and tetrazolyl.   The term "cycloalkoxy" refers to a hydrocarbon group whose alkyl radical is "alkyl" as defined above. It is understood to be a cycloalkoxy group having the above meaning.   The term "alkylthio-alkyl" refers to, for example, methylthiomethyl, ethylthiome Chill, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl Is understood to be 3-methylthiopropyl.   The term "alkenyl" refers to, for example, allyl, 1-methylallyl, 2-butenyl or Is understood to be 3-methyl-2-butenyl.   The term "alkynyl" refers to, for example, ethynyl, propargyl, 2-butynyl or It is understood to be 2-pentynyl.   Although it is not a group specifically mentioned above, a double or triple bond can be obtained from each group described above. By introduction of a group or by substitution with one or more identical or different substituents or CH or more₂For example NR³Others that can be induced by exchange with S, O, CO The same applies to all the groups described above.   Hydroxy groups, mercapto groups, etc. on commonly substituted groups, i.e. hydrocarbons. Or optionally containing a mono-substituted amino group, the hydrocarbon itself A group attached to another oxygen, sulfur or nitrogen atom at (eg hemiacetal and And hemiketal), unless otherwise stabilized by special groups It is unstable and therefore such groups are not preferred.   The present invention relates to all stereoisomers, especially individual enantiomers, which may occur in the compounds of the invention of the formula I Omers and their mixtures in any proportion and their salts, especially the acid addition salts. Including.   For the preparation of the preferred acid addition salts of compounds of formula I, hydrohalic acids such as Hydrochloric acid or hydrobromic acid and phosphoric acid, nitric acid, sulfuric acid, monofunctional or difunctional Carboxylic and hydroxycarboxylic acids such as acetic acid, succinic acid, fumaric acid, tartar Acids, citric acid, salicylic acid or lactic acid and sulfonic acids such as p-toluene Rufonic acid or 1,5-naphthalenedisulfonic acid can be considered. formula Acid addition salts of compounds of I can be prepared by conventional techniques for forming salts, eg Dissolved in an organic solvent and obtained in a simple way by adding acid then known By methods such as filtration, isolation and optionally washing with an inert solvent. Can be purified.   Base addition salts are hydroxides or carbonates of alkali metals or alkaline earth metals. It can be obtained by treatment with salts or organic amines.   A novel arylacetamide of formula I, for example in known manner as follows: Obtainable.   a) B is a group of formula VII and R^FiveIs hydrogen and the remaining substituents are described in formula I Aryl acetamides of formula I having the definition of are described, for example, in Synthesis (1985), 12 , 1153 in a manner similar to that described in formula IX (where R¹², R¹³Are independent of each other H, (C₁~ C₈) -Alkyl, (C₁~ C₈) -Haloalkyl or R¹²And R¹³Is 5 It may be a component of a-, 6- or 7-membered saturated or monounsaturated homocyclic ring. And the remaining substituents have the definitions given in formula I) to the dioxolanone of formula X ( Where each substituent has the definition given in formula I) It is obtained by treating with the amine.   The amine is, for example, Bull. Chem. Soc. Jap. 1990,63, 1252; Angew. Chem. 1 989,101, 202 and 1992,104, 914; Heterocycles, 1987,26, 1595 and J. Med. Chem. 1988,31, 1282, 1981,twenty four, 1063 and 1980,twenty three, 990, known methods.   This reaction is carried out at a temperature from 0 ° C to the boiling point of the mixture, preferably at a reflux temperature for 0.5 to 120 hours. It will be carried out over a period of time. The amine of formula X is 1-10 per equivalent of dioxolane of formula IX. The molar equivalents are preferably treated at 1-2 molar equivalents. This reaction is optionally inactive It is carried out in a solvent. Preferred solvents are ethers, aromatic or aliphatic hydrocarbons, Halogenated hydrocarbons, ketones, alcohols or mixtures thereof, especially diethyl Ether, dioxane, tetrahydrofuran, methyl tert-butyl ether, di Methoxyethane, toluene, xylene, chlorobenzene, hexane, cyclohex Sun, heptane, petroleum ether, acetone, methyl ethyl ketone, dichlorometa 1,1,2-dichloroethane, methanol or ethanol.   The dioxolanone of formula IX was prepared according to Organic Synthesis, Coll Vol. Org. Chem. Vol. 51 (19), 3747 (1986).   b) The compound of formula I is also represented by formula XI A carboxylic acid (wherein each substituent has the definition given in formula I) or optionally Reaction of formula XI (wherein each substituent has the definition given in formula I) obtained in the reaction system Treatment of a sex derivative with an amine of formula X, where each substituent has the definition set forth in formula I It is obtained by doing.   This method shows the acylation of a compound of formula X with a carboxylic acid of formula XI, wherein The reaction is carried out in the presence of an active compound of acid XI or a dehydrating agent or carboxylic acid XI or free Preference is given to working with the reactive derivative of form X.   Examples of derivatives of formula XI that are optionally prepared in the reaction mixture include, for example, An alkyl, aryl or arylalkyl ester of eg methyl, ethyl , Phenyl or benzyl esters, their imidazolides, their acids Halides such as acid chlorides or bromides, their anhydrides, aliphatics or Or an aromatic carboxylic acid, sulfonic acid or carbonic acid ester such as acetic acid, propylene Onic acid, p-toluenesulfonic acid or O-ethyl or O-isobutyl carbonate And their mixed anhydrides or their N-hydroxyimide esters. be able to.   Examples of said acid-active and / or dehydrating agents are chlorinated carbonates such as Ethyl rologate, isobutyl chloroformate, phosphorus pentoxide, N, N'-dicyclohexyl Rucarbodiimide, N, N'-carbonyldiimide, N, N'-carbonyldiimidazo And N, N′-thionyldiimide.   To activate the optionally produced carboxylic acid ester, for example titanium tet Laalkoxides such as titanium tetraisopropylate and titanium tetraethylate Or titanium tetramethylate, titanium tetrapropylate is used or This is achieved by increasing the pressure (Angew. Chemie, (1986), 6,569).   This reaction is carried out with a solvent such as methylene chloride, chloroform, carbon tetrachloride, ether. Ru, tetrahydrofuran, dioxane, benzene, Ruene, acetonitrile, N-methylpyrrolidine or dimethylformamide Or in a mixture of solvents, optionally with an inorganic base such as sodium carbonate or carbonate. Also, lithium or tertiary organic bases such as triethylamine and N-methylmorpholine Or in the presence of pyridine, which can also act as a solvent at the same time. In the presence of an acid activator, the reaction mixture may be mixed at -78 ° C to 120 ° C, preferably at -78 ° C. Suitably it is carried out at temperatures up to the boiling point. For this, the reaction mixture Isolating the optionally formed reactive derivative of the compound of general formula X or XI is It is not necessary, and furthermore, this reaction is carried out in excess of the compound of general formula X as solvent. Can also be implemented in.   Of the carboxylic acids and carboxylic acid derivatives of formula XI optionally obtained in the reaction mixture Manufacturing is known. For example, J. Org. Chem. (1978), 43, (13), 2702; Org. Syn th. (1945), 25, 33; Org. Synth. Col. Vol. IV, (1963), 110; Org. Synth. C ol. Vol. I, (1941), 336-SE 7604030-2, Synthesis (1975), 163, Synth. Comm un (1981), 11, 943; Org. Prep. Proced. (1970), 2,249, described in EP 140454 It is manufactured by a method similar to the method.   c) B is a group of formula VII and R^FourAnd R^FiveCompounds of formula I in which each is H are known Known oxidation methods (eg J. Org. Chem. (1987), 52, (22), 4978; Heterocy cles (1984) 22, (4), 773), where B is the corresponding case of formula I defined as the group of formula VI. Can be converted to a ton compound.   d) Compounds of formula I where B is a group of formula VI are known methods (eg J. Chem. S. oc. Perkin. Trans. I (1989), 1555) and B is a group of formula VII^Four And R^FiveCan be corresponding hydroxy compounds of formula I where each is hydrogen. Wear.   e) a formula in which B is a group of formula VII and the remaining substituents have the definition given in formula I Compound I is similar to those described in Tetrahedron Letters (1988), 44, (15), 4805. By the formula XII (where R¹⁴Is F, Cl, Br or I and the remaining substituents are A halo compound of formula I) having formula XIII (wherein each substituent is represented by formula I) (With the stated definitions). Wear. Compounds of structure XII are known or known methods (eg, J. Org. Ch. It can be obtained at em. (1955), 20, 237).   f) also B is a group of formula VII, R^FiveCompounds of formula I in which is not hydrogen are compounds of formula I Where B is a group of formula VII, R^FiveIs H) and the compound of formula ZR^Five(Where Z is nucleophilic Sex leaving groups such as Cl, Br, I, alkoxysulfonyl, alkylsulfonyloxy Or haloalkylsulfonyloxy, R^FiveHas the above definition) It can be obtained by treating with a killing agent and / or an acylating agent. This The reaction of J. Org. Chem. (1978), 43, 1893; Org. Synth. Col Vol I, (1941), 12; Conducted in the same manner as described in Tetrahedron Letters (1980), 21, (52), 4997. Can be done.   g) Also, the compound of formula I has the formula XIX             A-CH (OH) -CONH₂    (XIV) Compounds in known ways (eg Chemical Abstracts35, 3634) Closed formula XV To give a compound of the formula               A′-X-Q Obtained by reacting with a compound of the formula (wherein Q is a leaving group such as halogen). Can be   The compounds of the present invention of formula I have excellent fungicidal activity against phytopathogenic fungi. There are features. The compounds are of particular value because of their therapeutic activity. This is a conventional fungicide Is it particularly important in fungal diseases that cannot be effectively suppressed by drugs? One advantage. The spectrum of activity of the compounds of the present invention shows various economically important plant pathogens. Sexual fungi such as Phytophthora infestans and Includes Plasmopara viticola.   The compound is for treating seeds of cultivated crops to prevent seed-derived diseases. Can be used.   The compounds of the present invention are used in industrial fields such as wood preservatives for paints and thickeners. , As a preservative in cooling lubricants for metalworking or as boring oil and It is also suitable for use as a preservative in toning oils.   The compositions according to the invention generally contain 1 to 95% by weight of active ingredient.   The composition may be prepared by biological and / or physicochemical factors in various ways. Can be Lubricating powder (WP), emulsifying concentrate (EC) and (SC) are examples of possible formulations. Aqueous dispersions in oil or water as suspoemulsion ( SC), powder (DP), pest control agent, Water dispersible granules (WG) form granules, UV-formulations, microcapsules, waxes or You can give food. Aufl. 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N ． Y., 2nd Ed. 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Ed. 19 79, G. Goodwin Ltd. Listed in London.   The necessary pharmaceutical additives are also inert substances, surfactants, solvents and other additions. Known as agents, for example Watkins, “Handbook of Insecticide Dust Dilu ents and Carrier ”, 2nd Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons , N.Y .; Marschen, "Solvents Guide", 2nd Ed., Interscience, N.Y. Y. 1950; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridge -wood N. J. ; Sisley and Wood, "Encyclopedia of Surface Active It   Based on these formulations, other pesticidal active substances, fertilizers and / or Combinations with plant regulators are for example in the form of ready-to-eat formulations or tank mix (tan k mix).   Wettable powders are uniformly dispersible in water and, in addition to the substances mentioned above, are diluents or inerts. Sexual agents such as surfactants such as polyoxyethylated alkyl Killphenols, polyoxyethylated fatty alcohols, alkyls or alkyls Luphenol sulfonates and dispersants such as sodium lignin sulfonate , Sodium 2,2'-dinaphthyl-methane-6,6'-disulfonate, sodium Dibutylnaphthalene sulfonate or / and oleylmethyl taurine nato It is a formulation that also contains a sulphate salt. Emulsifiable concentrates contain active ingredients in organic solvents, such as broth. Tanol, cyclohexanone, dimethylformamide, N-octylpyrrolidone , Xylene or high boiling aromatics or hydrocarbons to dissolve one or more emulsifiers It is prepared by adding. Examples of emulsifiers include alkyl aryl sulfo. Calcium salts of acids such as calcium dodecyl benzene sulfonate or On-type emulsifiers such as fatty acid polyglycol ester, alkylaryl polyglyceride Coal ether, fatty alcohol polyglycol ether, propylene oxide , Ethylene oxide, sorbitan fatty acid ester, polyoxyethylene sorbita Fatty acid ester or polyoxyethylene sorbitan ester it can.   Dusts contain active ingredients in the form of finely divided solid substances, for example talc, natural clays such as kaolin, vesicles. Obtained by grinding with tontonite, pyrophyllite or diatomaceous earth Can be Does the granule partition the active ingredient onto an absorbable granular inert material? Is a concentrate of the active ingredient which can be used as an adhesive such as polyvinyl alcohol, sodium polyacetate. Carriers such as sand, kaolinite or granulated minerals with relate or mineral oil are used. It can be prepared by applying to the surface of the active substance. Suitable active ingredients may also be used Granulated in the usual manner for the preparation of fertilizer granules as a mixture with fertilizer. Can be   The concentration of the active ingredient in the wettable powder is, for example, about 10-9%, which is 100% The remaining ingredients up to consist of conventional formulation parts for formulation. Active in emulsifiable concentrates The concentration of the components is about 5-80%. Powder formulations contain at most 5-20%. Into granules Where the active ingredient content is in part that the active compound is a liquid or a solid Depending on which compound is liquid or solid and which condyle It depends on whether granular materials, fillers, etc. are used.   In addition to the active ingredient formulations mentioned, in some cases conventional adhesives, surfactants, Powders, emulsifiers, penetrants, solvents, fillers or carriers can be present.   In use, concentrates in commercially available form are usually diluted by conventional means. Be done. For example wettable powders, emulsifiable concentrates, dispersions and finely divided granules also use water To be diluted.   Dust and granule formulations and nebulizable solutions are generally not diluted and then further Used in combination with another inert substance.   For other conditions such as temperature, humidity, etc., the required usage rate may vary. . It has a wide range, for example 0.005 to 10.0 kg / ha or more of active substance, for example 0.01 It can be limited within the range of ~ 5 kg / ha of active substance.   The active ingredient of the invention may be used alone or in combination with other fungicides known in the literature. And can be used in commercially available formulations.   The compounds of the present invention are the best known fungicides such as (i) a conazole steroid demethylation inhibitor, (ii) linked to piperidine or 2,6-dimethylmorpholine via the N-atom 1- [3- (4-tert-butylphenyl) -2 -Methylpropyl] group-based steroid reduction inhibitor, (iii) dithiocarbamate fungicide, (iv) a chloroalkylthio group, optionally hydrogenated via an N-atom. A phthalimide fungicide attached to a ruimide group, (v) anilide fungicide, (vi) mbc fungicide, (vii) carbamate fungicide, (viii) a copper compound fungicide, (ix) tin compound fungicide, (x) a strobilurin type fungicide and (xi) Anilinopyrimidine (xii) Phosphorus content compound (xiii) chlorothalonil, dimethomorph, fe Fenpiclonil, fluazinam, hymexaz ol), nuarimol, pencycuron, pyrifenox (py rifenox), thicyofen (thicyofen), probenazole (probenazale), pirokiro (Pyroquilon), tricyclazole, quaternary ammonium compounds , Fludioxonil, 5-chloro-2-methyl-4-isothiazo Phosphorus-3-one, 2-methyl-4-isothiazolin-3-one (and these 2 Mixture of two), furmecyclox, 3-iodo-2-propini Fungicides selected from the group consisting of rubutyl carbamate and sulfur May be combined with a compound selected from   Conazoles are imidazole or 1,2,4-triazole according to ISO standard 257. Defined as a compound based on an azole and containing a halogenated phenyl group ing. Examples include prochloraz (and its metal complexes-especially manganese or copper. Complex), propiconazole, flusilazole, hexaconazole, tebuconazo , Difenoconazole, bromconazole, cibroconazole, diniconazo , Fenbuconazole, imibenconazole, fluconazole, tetracona Sol, microbutanyl, penconazole, fluquinconazole, azaconazo , Imazalil, triflumizole, epoxyconazole, trithiconazole, Mention may be made of metconazole and fungicides having the code No SSF 109. .   Examples of fungicides of type (ii) above include fenpropimorph and fenpropidi Can be mentioned.   Examples of the type (iii) fungicides include mancozeb and thiram. it can.   Examples of fungicides of type (iv) above include folpet, captafol and capta. Can be mentioned.   Examples of the (v) type fungicide include a) 3 ', 5'-dichloroanilide fungicide (where the anilino nitrogen is Form a ring carrying two oxo substituents in adjacent positions) eg ipro Dione, vinclozolin or procymidone or b) acetanilide fungicides such as metalaxyl or ofrase, c) sulfanilide fungicides such as diclofluanid, d) Benzanilide fungicides such as flutolanil and e) Heteroarylanilide fungicides such as tifluzamide, Can be mentioned.   Examples of type (vi) fungicides include carbendazim, benomyl and thiopha Mention may be made of nato-methyl.   Examples of the (vii) type fungicides include dietofencarb and propamocar I can mention Bubu.   Examples of the fungicide of the type (viii) include Bordeaux mixture, oxine- Mention may be made of copper, copper oxychloride and copper naphthenate.   Examples of fungicides of type (ix) above include tributyltin oxide and tributyl Examples include tin naphthenate.   Strobilurin type fungicide ((x) type fungicide) is arylacetate methyl ester Ter, where the acetic acid is further methoxymethylene or methoxyimino It carries a substituent. The aryl group is usually a 2-substituted phenyl group. The compound Examples of products include many patent applications such as European Patent Nos. 178826, 203606, 20. 3608, 206523, 229974, 226917, 242070, 242081, 243012, 2430 No. 14, 251082, 256667, 260794, 260832, 267734, 270252, 273572 No., 274825, 278595, 291196, 299694, 307101, 307103, 310954 , 312221, 312243, 329011 and 336211. You can The specific compound is code No. BAS 490F and No. Have ICIA 5504 Compound.   Examples of the (xi) type fungicides include pyrimethanil, cyprodinil and mepani. Pyrim can be mentioned.   Examples of the (xii) type fungicides include pyrazophos, fosetylaluminum and And tolclofos-methyl.   The names cited in the above compounds are generic names, not trade names, and their chemical structures are For example, “Pesticide Manual”, ninth edition, 1991, British Corp Protection  Found by reference to Council Publications or in other recent publications Can be.   In addition to the above, commercial formulations as well as ready-to-use forms obtained from these formulations The compound of the present invention includes other active ingredients such as insecticide, desiccant, sterilizer, acaricide, It can be mixed with nematicides or herbicides. Examples of insecticides include phosphate Stells, carbamates, carboxylates, formamidines, tin compounds, microbiota Examples thereof include compounds produced from products.   The preferred mixing partner is selected from the following 1 to 4. 1. Phosphorus compound group   Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, te Bupirimiphos, bromophos, bromophos-ethyl, cadusaphos, chlorphene Vinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton , Demeton-s-methyl, demeton-s-methyl sulfone, dialyphos, diazide Non, dichlorvos, dicrotophos, chlorethoxyphos, dimethoate, dis Lufoton, EPN, Ethion, Etoprophos, Etrimphos, Famful, Fena Miphos, phenytrithione, phensulfothione, fenthion, honophos, Formothion, heptenophos, isazophos, isothioate, isoxathion , Malathion, methacrifos, methamidophos, methidathion, mevinphos, mono Crotophos, Naredo, ometoate, oxydemethone-methyl, parathion, parathion-me Chill, Fentioart, Holat, Hosalon, Phosphorane, Phosmet, Phos Famidon, Poxime, Pirimiphos-ethyl, Pirimiphos-methyl, Profeno Phos, propaphos, propetamphos, prothiophos, pyraclofos, pyridapene Thione, quinalophos, sulprophos, temephos, terbufos, tetrachlorbin Phos, thiomethone, triazophos, trichlorfon, bamidthione. 2. Carbamate group   Aldicarb, 2-sec-butylphenylmethyl carbamate (BPMC), carba Lil, carbofuran, carbosulfan, chloetocarb, benfracarb, et Thiophenecarb, furatiocarb, isoprocarb, methomyl, 5-methyl- m-cumenyl butyryl (methyl) carbamate, oxamyl, pirimicarb, prem Ropoxyur, thiodicarb, thiophanox and alanylcarb. 3. Pyrethroid carboxylate group   Acrinathrin, allethrin, α-cypermethrin, 5-benzyl-3-free Rumethyl- (E)-(IR) -cis-2,2-dimethyl-3- (2-oxothiolane-3- Ylidenemethyl) cyclopropane-carboxylate, bioallethrin, bioa Resulin ((s) -cyclopentyl isomer), bioresmethrin, biphenate, Cycloprothrin, cyhalothrin, cypermethrin, cyphenothrin, deltame Surin, Empensulin, Esfenvalerate, Fenfluthrin, Femp Lopasulin, fenvalerato, flucislinate, flumethrin, fulvalina (D-isomer), bifenthrin, Permethrin, pheosulin (R) -isomer), d-praresulin, pyrethrins (Natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin . 4. Other   Amitraz, Fenbutatin oxide, Abamectin, Bacillus thuringien Cis (Bacillus thuringiensis), bensultap, vinapacryl, bromopropyi Rate, buprofezin, cartap, chlorobenzilate, chlorofluazuron , Clofentezine, chlorfluazuron, cyromazine, decofol, hexaf Lumuron, diflubenzuron, N- (2,3-dihydro-3-methyl-1,3-thiazo 2-ylidene) -2,4-xylidine, ginobton, zinocap, endosul Fan, etofenprox, (4-ethoxyphenyl) (dimethyl) (3- (3-phenoxyphenyl) propyl) silane, silafluofene, fenpro Ximate, fenazaquin, phenoxycarb, fipronil, fluazuron, Flufenoxuron, Flubenzimine, Flucycloxuron, Flufenox Xulon, γ-HCH, hexathiazox, hexaflumuron, hydramethyl Non, imidacloprid, ivermectin, lufenuron, acetamiprid, Nithiazine, Propargite, Pymetrozine, Pyrrolene, Pyridaben, Triazoma , Tebufenozide, tebufenpyrrode, teflubenzuron, tetradiphone , Tetrasul, thiocyclam, triflumuron.   The active ingredient content in the ready-to-use form prepared from the commercial formulation is 0.00 A wide range of concentrations from 01 to 95% by weight, preferably 0.001 to 1% by weight can be varied. Application is In a customary manner adapted to the individual application Be implemented.   The present invention is described below by way of examples, which do not limit the invention. A. Prescription example a) The powder composition comprises 10 parts by weight of active ingredient and 90 parts by weight of talc as inactive ingredient. Are obtained by mixing and then pulverizing in a hammer mill. b) Wettable powders that are easily dispersible in water consist of 25 parts by weight of active ingredient and quartz as inactive ingredient. 65 parts by weight of kaolin, 10 parts by weight of potassium lignin sulfonate and wet Or 1 part by weight of sodium salt of oleylmethyl taurine as a dispersant is mixed It was then obtained by grinding in a pinned disk mill. c) Dispersible concentrates readily dispersible in water are 40 parts by weight of active ingredient sulfosuccinate half s. With 7 parts by weight of tellurium, 2 parts by weight of sodium lignin sulfonate and 51 parts by weight of water Prepared by milling and then milling to less than 5 microns in a milling ball mill. It was d) Emulsifiable concentrate is 15 parts by weight of active ingredient, and 75 parts by weight of cyclohexanone as a solvent. And 10 parts by weight of nonylphenol ethoxylate (10 AeO) as emulsifier. Made e) Granules are 2 to 15 parts by weight of active ingredient and inert granule carrier material such as attapardi. Prepared from kite, pumice granules and / or quartz sand. Solid from example b) above A suspension of wettable powder with a solids content of 30% is sprayed onto the surface of attapulgite granules. It is suitable to dry, then mix intimately. Granules prepared in this way Comprises about 5% by weight wettable powder and about 95% by weight carrier material. B. Compound Examples   The structure of the resulting compound was confirmed by nmr and / or other suitable analysis. It was Example 1 N- [2- (3,4-dimethoxyphenyl) ethyl] -4-chloromandelamide   2,2-dimethyl-4- (4-chlorophenyl) -1, dissolved in 250 ml of acetone, 2- (3,4-dimethoxyphenyl) was added to a solution of 269.5 g (1.19 mol) of 3-dioxolanone. ) 323.3 g (1.78 mol) of ethylamine was added. Stir this mixture at 50 ° C for 24 hours did. The low-boiling substances are distilled off in a vacuum, the residue is dissolved in 1500 ml of ethyl acetate and 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride Washed with 1000 ml of each solution. Organic after drying the organic phase over sodium sulfate The phases are concentrated, the residue is suction filtered and then 4 times with 500 ml of n-pentane each. Washed twice. Pale beige solid 377 with mp 100-101 ° C after vacuum drying 0.8 g (90.5% of theory) was obtained. Example 2 N- (3-phenylpropyl) -4-trifluoromethylmandelamide   2,2-Dimethyl-4- (4-trifluoromethylphenyl) dissolved in 25 ml of ether Phenyl) -1,3-dioxolanone 3 g (0.0115 mol) in a solution of 3-phenylpro 1.55 g (0.012 mol) of pyramine was added. The mixture was stirred at room temperature for 16 hours . The precipitate is filtered off with suction, washed with a little ether and n-pentane and then dried under vacuum. Dried mp 107 ° C 30 g (77% of theory) of a white solid substance having were obtained. Example 3 N- (1-phenylcyclopentyl) -methyl-4-chloromandelamide   2,2-Dimethyl-4- (4-chlorophenyl) -1,3 dissolved in 25 ml ether -In a solution of 2.2 g (0.009 mol) of dioxolanone (1-phenylcyclopentyl) 3.06 g (0.0175 mol) of methylamine was added. Stir this mixture at room temperature for 16 hours did. It was taken up in 100 ml of ethyl acetate and the organic solution was diluted with 1N hydrochloric acid and saturated carbonic acid. Wash with 100 ml each of aqueous sodium hydrogen and sodium chloride, then The organic phase was dried over sodium sulfate. After removing the solvent in vacuum, mp 84 ° C 2.9 g (87% of theory) of a white solid substance were obtained. Example 4 N- [2- (3,4-dimethoxyphenyl) ethyl] -α-propargyl-4-ku Lorromandelamide   2,2-Dimethyl-4- (4-chlorophene) dissolved in 5 ml of tetrahydrofuran Nil) -4-propargyl-1,3-dioxolanone in a solution of 3.97 g (0.015 mol) 2- (3,4-dimethoxyphenyl) -ethylamine 4.08 g (0.0225 mol) was added. It was The mixture was stirred at 60 ° C. for 16 hours and the low boiling point solvent was vacuum distilled. Vinegar residue Taken up in 100 ml of ethyl acidate, 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and Washed with 100 ml each of sodium chloride. Dry the organic phase over sodium sulfate After drying and removing the solvent in vacuo, 5.0 g (86% of theory) of a colorless oil are obtained. Was obtained. Example 5 N-methyl-N- [2- (3,4-dimethoxyphenyl) ethyl] -4-chloromer Anderamide   2,2-Dimethyl-4- (4-chlorophenyl) -1,3-dioxolanone 3.0 g (0 0.013 mol) under stirring with N- [2- (3,4-dimethoxyphenyl) ethyl] methyl 5.08 g (0.026 mol) of Min was added. After stirring for 16 hours at room temperature, the reaction mixture is vinegared. Taken up in 100 ml of ethyl acidate, 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and Washed with 100 ml each of sodium chloride. Dry the organic phase over sodium sulfate After drying and separating the low-boiling substances in vacuum, 2.2 g of a pale yellow oil (theoretical amount of 4 6%) was obtained. Example 6 N- [2- (3,4-dimethoxyphenyl) ethyl] -N, O-dimethyl-4-chloro Mandelamide   N- [2- (3,4-dimethoxyphenyl) dissolved in 100 ml of dimethylformamide. Ru) Ethyl] -4-chloromandelamide 5.0 g (0.0143 mol) in a solution with stirring 1.25 g (0.313 mol) of 60% sodium hydride was added dropwise at 0-10 ° C. 30 at 10 ° C After the lapse of minutes, 5.82 g (0.0313 mol) of methyl iodide was added dropwise and the mixture was added at this temperature. It was stirred for 1 hour and then at room temperature for 2 hours. The reaction mixture was poured into ice-water, each It is extracted twice with 200 ml of ethyl acetate and the combined organic phases are dried over sodium sulphate and then And concentrated in vacuo. The residue is silica gel (ethyl acetate / petroleum ether 1: 1). ). 4.5 g (83% of theory) of a pale yellow oil were obtained. Example 7 5- (4-chlorophenyl) -3- [2- (3,4-dimethoxyphenyl) Lu) ethyl] -1,3-oxazolidin-4-one   N- [2- (3,4-dimethoxyphenyl) dissolved in 100 ml of dimethylformamide. Ru) Ethyl] -4-chloromandelamide 5 g (0.0143 mol) in a solution with stirring, 1.25 g (0.313 mol) of 60% sodium hydride was added dropwise at 0-10 ° C. 3 at 0-5 ° C After 0 minutes, 5.832 g (0.0313 mol) of dibromomethane was added dropwise, and the mixture was mixed with 0-5. The mixture was stirred at ℃ for 1 hour and then at room temperature for 2 hours. The reaction mixture was added to 800 ml of ice-water, Extracted twice with ethyl acetate, the combined organic phases are dried over sodium sulphate and then vacuumed. Concentrated in. Filter the residue through silica gel (ethyl acetate / petroleum ether 1: 1). After this, 3.0 g (58% of theory) of a pale yellow oil were obtained. Example 8 O-acetyl-N- [2- (3,4-dimethoxyphenyl) ethyl] -4-bromo Mandelamide   N- [2- (3,4-dimethoxyphenyl) dissolved in 50 ml of methylene chloride Ethyl] -4-bromomandelamide (Compound 25) 1.0 g (0.0025 mol) solution To this, 1.75 g (0.02 mol) of acetyl chloride in 10 ml of methylene chloride was added dropwise. After 10 minutes at 0-10 ° C, 2.02 g (0.02 mol) of triethylamine was added dropwise and the mixture was added. The mixture was stirred at this temperature for 1.5 hours. Saturate the reaction mixture after addition of 5 ml of methanol Add to 150 ml of sodium hydrogen carbonate aqueous solution, extract twice with methylene chloride, and combine. The combined organic phase was dried over sodium sulfate. The residue is silica gel (ethyl acetate / stone) 3.7 g of a beige solid (mp 91 ° C.) after filtration with oil ether 1: 1) 94% of theory) was obtained. Example 9 N- [2- (3,4-dimethoxyphenyl) ethyl] phenylglyoxylylami Do   N- [2- (3,4-dimethoxyphenyl) ethyl ether dissolved in 100 ml of chloroform. A solution of 3.15 g (0.01 mol) of mandelamide under stirring and reflux. 5.22 g (0.06 mol) of manganese oxide were added dropwise. Mixing after 2 hours under reflux The product was filtered, and the filter cake was boiled 3 times with 150 ml of chloroform each. Wash once with hot chloroform. When the solvent is separated in vacuum, mp 80 ° C 3.0 g (96% of theory) of colorless solid were obtained. Example 10 N- [2- (3,4-dimethoxyphenyl) ethyl] phenylglyoxylylami Do   Phenylglyoxylyl chloride 3.37 dissolved in 40 ml of dry methylene chloride g (0.02 mol) in a solution of 2- (3,4-dimethoxyphenyl) under stirring at room temperature. Ethylamine 4.35 g (0.022 mol) and triethylamine 2.42 g (0.022 mol) The mixture of) was added dropwise. The reaction mixture was warmed at 42 ° C. The reaction mixture after 30 minutes It is poured into 40 ml of 2N hydrochloric acid and the organic phase is saturated aqueous sodium hydrogen carbonate solution and sodium chloride. Wash with 50 ml of each of the barium, dry over sodium sulfate and then low boiling Was vacuum distilled. 5.7 g (91% of theory) of a colorless solid having an mp of 80 ° C are obtained. It was Example 11 N- [2- (3,4-dimethoxyphenyl) ethyl] -2-fluoro-4-trif Luoromethyl mandelamide   2-fluoro-4-trifluoromethyl mandelic acid under nitrogen (1.00 g) and N-hydroxysuccinimide (0.48 g) were dried over dimethoxyethane. Dissolved in tan (50 ml) at room temperature. Dicyclohexylcarbodiimide (0.87g) Was added once and a white precipitate (dicyclohexylurea) was obtained after 10 minutes. Further at room temperature After stirring for 15 minutes, 2- (3,4-dimethoxyphenyl) ethylamine (0.86 g) Was added. The suspension is stirred for 2 hours, the dicyclohexylurea is filtered off and the residue Was evaporated. 3.0 g of crude material is obtained, which is chromatographed on silica gel ( It was purified by ethyl acetate) and then recrystallized from diisopropyl ether. Yield: 1.52g = 90.5% of theory mp 108-109 ° C Example 12 N- [2- (3,4-dimethoxyphenyl) ethyl] -4-cyanomandelamide   4-Cyano in dry dichloromethane (8 ml) and pyridine (0.67 ml) Mixing of mandelic acid (0.7 g, 4.0 mmol) and catalytic amount of dimethylaminopyridine Trimethylsilyl chloride (1.1 ml) was added dropwise to the mixture under stirring. This mixture Stir at room temperature for 4 hours, cool to 0 ° C., and add 3 drops of dimethylformamide followed by oxalic acid. Luchloride (0.36 ml) was added. The mixture is stirred at 0 ° C. for another hour and then at room temperature for 30 minutes. I stirred. It was cooled to 0 ° C. and 2- (3,4-dimethoxide in dry pyridine (1 ml) was added. Cyphenyl) ethylamine (0.8g) was added. The mixture was stirred at room temperature for 2 hours . Citric acid (0.92g) in methanol (8ml) was added and the mixture was 1/2 at room temperature. Stirred for hours. I left it overnight. Ethyl acetate (50 ml) was added and the solution was added to 1 Wash with N hydrochloric acid (40 ml), The aqueous extract was extracted with ethyl acetate. The extract was saturated with aqueous sodium hydrogen carbonate Wash with liquor (15 ml), brine (15 ml), dry and evaporate. Remove the residue Purified by silica gel chromatography, 0.9 g of product was obtained as brown gum. It was obtained. Example 13 N- [2- (3,4-dimethoxyphenyl) -2-hydroxy-1,1-dimethylethyl ester ]]-4-chloromandelamide   Methyl 4-chloromandelate (0.44 g) and 2-amino-2- (3,4-dimeme Toxiphenyl) -2-methylpropanol (0.86 g) mixture together 120-1 Heated at 30 ° C. for 4 hours. The gum obtained is taken up in ether and the solution is Evaporated. The residue was chromatographed on silica gel (ethyl acetate / petroleum ether). (Bp 60-80 ° C); 4: 1) to give 0.35 g of product as a glass. Obtained (R_f= 0.5). Example 14 N-phenylethyl mandelamide   Produce a solution of sodium (1.27g) dissolved in methanol (25ml) and cool did. Mandelamide (7.6 g) and carbonic acid dichloride dissolved in methanol (20 ml) A solution of ethyl (6.5g) was added. The white solid precipitate obtained is heated to 70 ° C to dissolve it. I understand. The mixture was maintained at this temperature for 1 hour. Evaporate the methanol and cool it The resulting liquid was dissolved in water (75 ml) and acidified to pH 1 with concentrated hydrochloric acid. Vinegar mixture Extract with ethyl acidate, dry the extract and evaporate to remove 5-phenyloxazolidi Yield 2,4-dione. mp 95-98 ° C.   This product (4.4 g), anhydrous potassium carbonate (3.75 g) and aceto The mixture of benzene (75 ml) was stirred at room temperature for 1 hour. 2- in acetone (25 ml) Bromoethylbenzene (3.5 ml) was added and the mixture was heated under reflux overnight. The mixture was filtered, the filtrate was evaporated and extracted with diisopropyl ether. Extract Is evaporated, the residue is cooled and 3- (2-phenylethyl) -5-phenyloxy Sazolidine-2,4-dione was obtained. mp 82-83 ° C.   This product was nitrogen purged with dry methanol (50 ml) then solid sodium. Added to methoxide (0.29g). The mixture was shaken for 5 hours, poured into dilute hydrochloric acid, The organic layer was evaporated and then extracted with ethyl acetate / water, the organic layer was washed with water and dried. Evaporation then gave 0.48 g of the title product as an oil. Example 15 N- [2- (3,4-dimethoxyphenyl) ethyl] -O-methyl-3,4-dichloro Mandelamide   2- (3,4-dimethoxyphenyl) ethylamine (0.37 g) was added to methyl-O-meth. Add chill-3,4-dichloromandelate (0.37 g) and stir the mixture for 3 hours at 103 ° C. Heated to. The mixture was extracted with ethyl acetate and the extracts washed with 2M hydrochloric acid. Organic The fractions were dried over magnesium sulphate, filtered and the solvent was evaporated. The rest The distillate was purified by silica gel chromatography to give the title product as a yellow oil. As a 55% yield. Example 16 N- [2- (3,4-dimethoxyphenyl) -1,1-dimethylethyl] -4-chloro Mandelamide   Diisoprene dissolved in dry tetrahydrofuran (150 ml) under nitrogen Butyllithium (32 ml) was added to lopyramine (8.08 g) with cyridin at -60 ° C. It was added dropwise. The mixture was warmed to −5 ° C. and then cooled again to −60 ° C. Treated with a solution of isobutyric acid (3.52 g) dissolved in orchid (20 ml). Mix the room temperature Warm to room temperature and add 1,3-dimethyl-3,4,5,6-tetrahydrofuran in tetrahydrofuran (15 ml). Trahydro-2 (1H) -pyrimidinone (5.12g) was added. Room temperature of the mixture It was stirred for 5 hours. To the mixture was added 3,4-dimethonitrile in tetrahydrofuran (15 ml). Xybenzyl chloride (7.44g) was added via syringe at -5 ° C. The mixture Stirred at room temperature for 16 hours. Saturated ammonium chloride (10 ml) was added. Hydroxide mixture It was extracted with aqueous sodium chloride solution (7%). The extract was extracted with ether. Aqueous layer Was acidified with hydrochloric acid. The solid is extracted with dichloromethane, the extract is dried and then Evaporated. The residue was triturated with cold water and filtered. White solid dichloromethane Extracted with, dried and evaporated to give 3- (3,4-dimethoxyphenyl) -2,2-dimethyl. Lupropionic acid was obtained. mp 102-108 ° C.   A suspension of the above product (4.9 g) suspended in toluene (10 ml) was thionyl chloride. Treated with lid (2.46 g) and the mixture was stirred at 80 ° C. for 2 hours. This mixture under reduced pressure The residual liquid was added to dry acetone (10 ml) and the solution was added to acetone (10 ml). 28 ml) and a stirred solution of sodium azide (2.68 g) dissolved in water (22 ml). Added at 0 ° C. Water (30 ml) was added to this solution and the mixture was extracted with toluene. Extraction The product was dried over magnesium sulfate and heated at 80-90 ° C for 2 hours with stirring under nitrogen. did. The mixture was cooled to room temperature, treated with concentrated hydrochloric acid (3.8 ml) and stirred at 80-90 ° C for 5 minutes. I stirred. It was cooled at room temperature, filtered and the flaky solids were collected after washing with ether. I have The filtrate is washed with water, dried and steamed. I fired. The residue was dissolved in tetrahydrofuran and concentrated hydrochloric acid (2 ml) was added. It was stirred for 20 minutes and evaporated. Dissolve the solid residue in water and add sodium carbonate. Basified with aqueous solution and extracted with dichloromethane. This was first dissolved in water Combined with the flaky solid, made basic, re-extracted with dichloromethane, two extracts Was dried and then evaporated to give 2- (3,4-dimethoxyphenyl) -1-methylpro Pyramine was obtained. mp 116-118 ° C.   This was then treated in the same manner as in Example 12 with trimethylsilyl chloride and 4-chloro. React with romandelic acid, then silica gel chromatography (ethyl acetate / Purified by petroleum ether (bp.60-80 ° C); 4: 1), the title compound is glass. Obtained as a substance (R_f= 0.5).   Representative examples of the compound of the present invention that can be produced as described above are disclosed in Tables 1 to 7 below. As is done. Test example   Various tests were carried out on the compounds of the present invention.   The compound was labeled with Phytophthora infestans (Toma End-of-life blight of rice (PI) and Plasmopara viticola ) (Grape downy mildew-PV) was evaluated.   An aqueous solution or dispersion of the compound at the desired concentration containing a wetting agent is applied to a suitable plant. Were sprayed on and then inoculated by spraying with a spore suspension of the fungus. Then plant The plant was kept under the control of environmental conditions suitable for maintaining the growth of the plant and disease occurrence. At the right time After the passage of time, the degree of infection on the leaf surface was visually evaluated. The following compounds of the present invention 2, 15, 20, 25, 39, 61, 62, 253, 258, 262, 275, 297, 298, 304, 740, 741, 762, 764, 767, 866, 1008, 1149, 1189, 1190, 1199, 1200, 1405, 2119, 2120 , 2134, 2151, 2173, 2174, 2177, 2182, 2183, 2214, 2215, 2216, 2221, 2228 , 2229, 2233, 2233, 2237, 2238, 2239 Below 500 ppm gave 100% inhibition of one or both of the above diseases.

[Procedure Amendment] Patent Act Article 184-8 [Submission date] March 6, 1995 [Correction content]                                 Specification         Aryl acetamides, their production method, and their         Compositions containing and their use as fungicides   The present invention relates to arylacetamides, methods for producing them, and compositions containing them. And their use as fungicides.   A substituted arylacetate having an optionally substituted hydroxy group attached at the α-position. Toamide is used as an active ingredient of herbicides (JP-5 8032-853) and for the treatment of skin diseases. It is described as a composition (EP-A-98743). Also, in the chemical literature as an intermediate There are many reference descriptions for all such compounds.   Moreover, in EP 71568, in particular, the α-position is substituted with an azolylmethyl group. Then, a similar compound, in which the nitrogen of the amide group can be substituted with a benzyl group, becomes an antifungal agent. Then claimed.   Surprisingly, new allies exhibit beneficial activity in combating fungi, especially phytopathogenic fungi. Luacetamide was found.   That is, the present invention provides a formula I for eradication of fungi. [In the formula,   A is an optionally substituted aryl group;   A'is an optionally substituted aryl group;   B is a carbonyl or methylene group (which may be optionally substituted hydroxy) And substituted by any further substituents);   X is an optionally substituted alkylene chain having 2 to 4 carbon atoms (wherein Any two substituents on either carbon are oxo or optionally substituted i Can form a mino group); and                             The scope of the claims 1. Formula I for eradication of fungi   [In the formula,     A is an optionally substituted aryl group;     A'is an optionally substituted aryl group;     B is a carbonyl or methylene group (which may be an optionally substituted hydroxy group). And optionally further substituted));     X has an optionally substituted alkylene chain having 2 to 4 carbon atoms (wherein Any two substituents on either carbon are oxo or optionally substituted Capable of forming an imino group); and     R⁷Is heterocyclyl, aryl, silyl, alkyl, alkenyl, cyclo Alkyl, alkynyl, cycloalkenyl, amino, hydroxy, mercapto ( Each of these optionally substituted), with hydrogen, cyano or acyl And where B is substituted with an optionally substituted hydroxy, then The substituent on the hydroxy of is R⁷Or with any other substituents on B. Can form a ring together with each other], its stereoisomers and And the use of mixtures thereof. 2. A is of formula II or III   Is a group represented by     A'is of formula IV or V   A group represented by the following formula;     m, n, m'and n'are integers;     m = 1-5;     n = 1 to 7;     m '= 0-5;     n '= 0-7;     R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₈ ) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁~ C₆ ) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Alkyl, (C₁ ~ C₈) -Heteroaryl, (C₁~ C₈) -Non-aromatic heterocyclyl, (C₁~ C₈) -Hete Lower aryl- (C₁~ C₆) -Alkyl, (C₁~ C₈) -Non-aromatic heterocyclyl- (C₁~ C₆) -Alkyl, cyano, nitro, halogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCO R³, -OCOOR³, -OCO-NR³R^Four, -SR³, -SOR³, -SO₂R³, -SO₂-OR³, -SO₂NR³R^Four, -NR³R^Four , -NR³-SO₂R^Four, -NR³-COR^Four, -P (O) (OR³) (OR^Four), -O-P (O) (OR³) (OR^Four) Or-SiR³ ₃ And     In the first 10 of these groups, optionally the following conditions:     a) when 1, 2 or 3 CH-CH- units are present in a non-cyclic state, Each is replaced by 1, 2 or 3 CH = CH-units,     b) 1 CH₂-CH₂-If the unit exists in a non-cyclic state, it is C≡C- Replaced by units,     c) When one CH-CH-unit is present in a ring, it is replaced by a C≡C-unit Can be exchanged,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O-CO-NR³R^Four, -SR³ , -SOR³, -SO₂R³, -SO₂-OR³, -SO₂-NR³R^Four, -NR³R^Four, -NR³-COR^Four, -P (O) (OR³) (OR^Four ), -O-P (O) (OR³) (OR^Four) And -SiR³ ₃Up to three identical or selected from the group Replaced by different substituents,     e) After substitution by d), the hydrogen atom remaining on a carbon atom which is not part of the ring is Partially or wholly replaced by the same or different halogen atoms,     f) a hydrogen atom present on a carbon atom which is part of a ring is a radical R³(R³= Is hydrogen Up to three identical or different selected from the substituents described in d)) Replaced by the substituent     g) After substitution by f), hydrogen atoms remaining on carbon atoms that are part of the ring Partially or wholly replaced by one or different halogen atoms,     h) one or two of which is present except when it is at the point of attachment of the group CH₂-Units are O, S, CO and NR³The same or different groups selected from the group Be replaced,   At least one of is satisfied;     R³And R^FourAre the same or different and independent of each other, hydrogen, (C₁~ C₁₈) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- ( C₁~ C₆) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Archi Le, (C₁~ C₈) -Heteroaryl or (C₁~ C₈) -Heteroaryl- (C₁~ C₆) -Archi Where in the first seven groups, optionally the following conditions:     a) when 1, 2 or 3 CH-CH- units are present in a non-cyclic state, Each is replaced by 1, 2 or 3 CH = CH-units,     b) 1 CH₂-CH₂-If the unit exists in a non-cyclic state, it is C≡C -Replaced by units,     c) When one CH-CH-unit is present in a ring, it is replaced by a C = C-unit Can be exchanged,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³′, -COOR³′, -CONR³′₂, -OR³′, -OCOR³′, -OCOOR³′, -O-CO -NR³′, -SR³′, -SOR³′, -SO₂R³′, -SO₂-OR³′, -SO₂NR³′₂, -NR³′₂, -NR³ ′ -COR³′, -P (O) (OR³) (OR^Four), -O-P (O) (OR³) (OR^Four) And -SiR³′₃Choose from a group of Replaced by up to 3 identical or different substituents     e) After substitution by d), the hydrogen atoms remaining on carbon atoms that are not part of the ring are Partially formed by the same or different halogen atoms. Or all are replaced,     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Is hydrogen Up to three identical or different selected from the substituents described in d)) Replaced by the substituent     g) After substitution by f), hydrogen atoms remaining on carbon atoms that are part of the ring Partially or wholly replaced by one or different halogen atoms,     h) 1 or 2 CHs present other than at the bonding position of the group₂-Unit is O, S, CO and NR³Replaced by the same or different groups selected from the group Is   At least one of:     R³And R^FourTogether (C₃~ C₆) -Alkylene group (where 1 CH₂-The basis is In some cases CO-, O, S or NR³Replaced by '));     R³′ Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Archi Nil, (C₁~ C₆) -Haloalkyl, (C₂~ C₆) -Haloalkenyl, (C₂~ C₆) -Haloal Quinyl, (C₃~ C₆) -Cycloalkyl, (C₃~ C₆) -Cycloalkyl- (C₁~ C_Four) -Archi Le, (C₆~ C_Ten) -Aryl, (C₇~ C₁₁) -Aralkyl and (C₁~ C_Five) -Heteroary The same or different groups selected from the group of The groups are cyano, nitro, halogen, (C₁~ C_Four) -Alkyl, (C₁~ C_Four) -Haloalkyl, (C₁~ C_Four) -Alkoxy, (C₁~ C_Four) -Haloalkoxy, phenyl, phenoxy, benzene One or two identical or different selected from the group of dil and benzyloxy Can have a substituent in the ring;     B is of formula VI or VII   Is the basis of;     R^FiveIs hydrogen, (C₁~ C₁₈) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Shi Chloalkyl- (C₁~ C₆) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- ( C₁~ C₆) -Alkyl, (C₁~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁ ~ C₆) -Alkyl, cyano, -COR³, -COOR³, -CONR³R^FourOr-SiR³ ₃(Where R³Oh And R^FourHas the above definition), where the groups described in the second to the eighth are R in combination¹And R²At least one of the conditions a) to h) specified for the radical Satisfied;     R⁶Is hydrogen or R¹With the definition given above for R^Five= With hydrogen R in some cases⁶Is not bonded via an O-, S- or N-atom, or     R^FiveAnd R⁶Together (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is C O, O, S or NR³Optionally replaced by'and / or present One of the CH-CH-units is optionally replaced with a C = C-unit);     R⁷Is hydrogen, or R above except for nitro and halogen.¹Described in Has a sense; or     R^FiveAnd R⁷Together (C₂~ C_Five) -Alkylene group (where 1 CH₂-The base is C O, O, S or NR³Optionally replaced by ' And / or one of the CH-CH-units present is a C = C-unit and optionally Exchanged) and R⁶Has the above definition;     R⁶And R⁷Together (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is C O, O, S or NR³Optionally replaced by'and / or present One of the CH-CH-units is optionally replaced by C = C-units) R^FiveHas the above definition;     X is the formula VIII             -CR⁸R⁹-(CR^TenR¹¹) p- (VIII)   Is the basis of;     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , R⁷Has the definition described above for or is halogen or nitro, And here R⁸And R⁹Or R^TenAnd R¹¹Or together, add an oxo group Can be O by forming, or     R^TenAnd R¹¹Group together = N-OR³Can be formed, or     R⁷And R⁸Together (C₂~ C_Five) -Forming an alkylene group, R⁷And R^TenIs Together (C₁~ C_Four) -Forming an alkylene group or R⁸And R^TenAre together ((C₃~ C₆) -Alkylene groups are formed, in which in each case one CH₂-The base is CO, O, S or NR³C optionally substituted by'and / or present One of the H-CH-units is optionally replaced by a C = C-unit and this ring bond Groups not related to have the above definitions; and     p is 1, 2 or 3;   Use of the compounds according to claim 1 and their salts, especially acid addition salts. 3. R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁~ C_Four ) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁~ C_Four) -Alkyl, (C₁ ~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C_Four) -Alkyl, cyano , Nitro, halogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -OCO -NR³R^Four, -SR³, -SOR³, -SO₂R₃, -SO₂-OR³, -SO₂NR³R^Four, -NR³R^Four, -NR³-SO₂R^Four, -N R³-COR^FourOr-SiR³ ₃Where, in the first 7 groups, these B), c), e), g) and h) of the above conditions defined for the groups and the following conditions:     a) When one CH-CH- unit is present in a non-cyclic state, it is CH = CH-replaced by units,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O-CO-NR³R^Four, -SR³ , -SOR³, -SO₂R³, -SO₂-OR³, -SO₂-NR³R^Four, -NR³R^Four, -NR³-COR^FourAnd-SiR³ ₃of Replaced by up to 3 identical or different substituents selected from the group:     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Is hydrogen Up to three identical or different selected from the substituents described in d)) At least one of the following is satisfied:     R³And R^FourAre the same or different and independent of each other , (C₁~ C₁₂) -Alkyl, (C₃~ C₈) -Cycloalkyl, (C₃~ C₈) -Cycloalky Le- (C₁~ C_Four) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁~ C_Four) -A Luquil, (C₁~ C₈) -Heteroaryl or (C₁~ C₈) -Heteroaryl- (C₁~ C_Four) -A Rukiru, and in the last seven groups described here, B), c), e), g) and h) of the above defined conditions and the following conditions:     a) When one CH-CH- unit is present in a non-cyclic state, it is CH = CH-replaced by units,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³′, -COOR³′, -CONR³′₂, -OR³′, -OCOR³′, -OCOOR³′, -O-CO -NR³′, -SR³′, -SOR³′, -SO₂R³′, -SO₂-OR³′, -SO₂NR³′₂, -NR³′₂, -NR³ ′ -COR³′ And -Si (R³′)₃Up to three identical or different selected from the group of Replaced by a substituent,     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³′ (R³′ = With hydrogen Up to three identical or selected from the substituents described in d) and d) Replaced by different substituents,   At least one of is satisfied;     R³'And B have the above definitions;     R^FiveIs hydrogen, (C₁~ C₁₂) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Shi Chloalkyl- (C₁~ C_Four) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- ( C₁~ C_Four) -Alkyl, (C₁~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C_Four)- Alkyl, cyano, -COR³, -COOR³, -CONR³R^FourOr SiR³ ₃(Where R³And R^FourIs (With the above definitions), where the 2nd to 8th groups are optionally R¹And R²At least one of the conditions a) to h) specified for the radical of is fulfilled;     R⁶Is hydrogen or R¹With the definition given above for R^Five= With hydrogen R in some cases⁶Is not bonded via an O-, S- or N-atom, or     R^FiveAnd R⁶Forms a ring as defined in claim 2;     R⁷Is hydrogen, or R above except for nitro and halogen.¹Described in Has a sense; or     R^FiveAnd R⁷Forms a ring as defined in claim 2;     R⁶And R⁷Forms a ring as defined in claim 2;     X has the definition of claim 2;     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , R⁷Has the definition described above for or is halogen, and wherein R⁸ And R⁹Or R^TenAnd R¹¹Together again to form an oxo group Can be more O, or     R^TenAnd R¹¹Group together = N-OR³Can be formed, or     R⁷And R⁸, R⁷And R^TenOr R⁸And R^TenIs the ring defined in claim 2 Done;     And the groups not related to this ring bond have the above definitions; and     p has the definition of claim 2,   Use of the compound according to claim 2. 4. R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₂~ C₁₂) -Alkenyl, (C₂~ C₁₂) -Alkynyl, (C₆~ C₁₂) -Ant , (C₇~ C₁₃) -Aralkyl, (C₁~ C₁₂) -Alkoxy, (C₂~ C₁₂) -Alkenylo Kish, (C₂~ C₁₂) -Alkynyloxy, (C₁~ C₁₂) -Alkylthio, (C₆~ C₁₂) -Ant Oxy, (C₇~ C₁₃) -Arylalkoxy, (C₇~ C₁₃) -Arylalkylthio , (C₆~ C₁₂) -Arylthio, heteroaryl, heteroaryl- (C₁~ C_Four) -Archi , Heteroaryloxy, heteroaryl- (C₁~ C_Four) -Alkyloxy, hetero Aryl- (C₁~ C_Four) -Alkylthio, heteroaryloxy- (C₁~ C_Four) -Alkyl ( Here, the heterocyclic aryl groups are each up to 8 carbon atoms and N, S and O. Having up to 4 identical or different heteroatoms selected from), (C₃~ C₁₂ ) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkoxy, (C₃~ C₁₂) -Cycloalkenyl , (C₃~ C₁₂) -Cycloalkenyloxy, -CN, OH, NO₂, F, Cl, Br, I, -COOR³ , -COR³, -OCOR³, -CONR³R^Four, -R³COR^Four, -NR³R^Four, -SO₂NR³R^Four, -NR³SO₂R^Four, -NR³CO R^Four, -SiR³ ₃, -SO₂R³Or-SO₃R³Where the first 23 groups are defined in claim 2 or Is optionally substituted in the manner described in 3,     R³And R^FourHas the definition of claim 2 or 3;     R^FiveAnd R⁶Are independent of each other, hydrogen, (C₁~ C₁₂) -Alkyl, (C₂~ C₁₂)- Alkenyl, (C₂~ C₁₂) -Alkynyl, (C₆~ C₁₂) -Aryl, (C₇~ C₁₂) -Aralchi Le, (C₇~ C₁₂) -Aryloxyalkyl, heteroaryl, heteroaryl- (C₁ ~ C_Four) -A Rualkyl, heteroaryloxy- (C₁~ C_Four) -Alkyl (wherein a heterocyclic aryl group Are each up to 8 carbon atoms and up to 4 carbon atoms selected from N, S and O Having the same or different heteroatoms), (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂ ) -Cycloalkenyl, COOR³, COR³, -CONR³R^FourOr-SiR³ ₃And here is the first The radicals 2-12 are optionally substituted by the process of claims 2 or 3. Cage or R^FiveIs R⁶Saturated or unsaturated 5-, 6-, 7- or 8-with Can form a member ring, and R³And R^FourHas the above definition, and R^FiveBut R if not hydrogen⁶Is also (C₁~ C₆) -Alkoxy, (C₁~ C₆) -Haloalkoxy, Phenoxy, CN, -NR³R^Four, -NR³SO₂R^FourOr-NR³COR^FourCan also be;     R⁷Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Arkini Le, (C₆~ C₁₂) -Aryl, (C₇~ C₁₂) -Alkaryl, (C₁~ C₆) -Alkoxy, (C₂~ C₆) -Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₆~ C₁₂) -Aryloki Si, (C₇~ C₁₃) -Alkaryloxy, heteroaryl, heteroaryl- (C₁~ C_Four)- Alkyl, heteroaryloxy, heteroaryl- (C₁~ C_Four) -Alkyloxy ( Here, the heterocyclic aryl groups are each up to 8 carbon atoms and N, S and O. Having up to 4 identical or different heteroatoms selected from), (C₃~ C₈) -Cycloalkyl, (C₃~ C₈) -Cycloalkoxy, (C₃~ C₈) -Cycloalkenyl, ( C₃~ C₈) -Cycloalkenyloxy, -OH, COOR³, COR³, -OCOR³, CONR³R^Four, NR³CO R^Four, SiR³ ₃Or NR³R^FourWherein the groups described in the above 2nd to 19th groups are Or described in 3 Optionally substituted by the method, and R³And R^FourHas the above definition, and Is R⁷Is R^FiveOr R⁶Together with a portion of the saturated or unsaturated 5- or 6-membered ring Formed;     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , F, Cl, Br, I, CN or R⁷Has the above definition for, or R⁷And R⁸, R⁷And R^TenOr R⁸And R^TenIs saturated or unsaturated 5- or 6- , 7- or 8-membered ring, and the remaining groups and variables are defined in claim 2 or Has the definition given in 3,   Use of a compound according to claim 2 or 3. 5. R¹And R²Are the same or different and independent of each other, and (C₁~ C₆ ) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃~ C₇) -Cycloa Luquil, (C₃~ C₇) -Cycloalkenyl, (C₃~ C₆) -Alkoxy, benzyloxy, (C₁~ C₆) -Alkylthio, phenyl, phenoxy, phenylthio, (C₂~ C₆) -Al Kenyloxy, (C₃~ C₆) -Alkynyloxy, (C₇~ C₁₃) -Phenylalkoxy, ( C₇~ C₁₃) -Phenylalkylthio, (C₁~ C₆) -Haloalkyl, (C₁~ C₆) -Haloal Koxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyloxy, special Fluoroalkyl and fluoroalkoxy, (C₃~ C₇) -Cycloalkyl oki Si, (C₃~ C₇) -Cycloalkenyloxy, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆) -Haloalkenylthio, (C₃~ C₇) -Halocycloalkyl, (C₃~ C₇) -Halocycloa Lucenyl, (C₃~ C₇) -Halocycloalkoxy, (C₃~ C₇) -Halocycloalkenylo Kish, (C₃~ C₇) -Halocycloalkylthio, especially fluoro Alkylthio, CN, OH, NO₂, F, Cl, Br, I, CO₂R³, OCOR³, COR³, NR³COR^Four, NR³R^Four, SO₃R³, SO₂NR³R^Four, Heteroaryl, heteroaryloxy (where Each of the cyclic aryl groups is selected from up to 5 carbon atoms and N, S and O Up to 3 identical or different heteroatoms), and     R³And R^FourHas the above definition;     m = 1-5;     n = 1 to 4;     m ′ = 2-5;     n '= 2-4;     R^FiveAnd R⁶Are the same or different and independent of each other, hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Alkynyl, (C₃~ C₇) -Cycloal Kill, (C₃~ C₇) -Cycloalkenyl, phenyl, heteroaryl (wherein heterocycle The formula aryl groups are each selected from up to 5 carbon atoms and N, S and O Up to 3 identical or different heteroatoms), (C₁~ C₆) -Hydroxy Alkyl, (C₁~ C₆) -Haloalkyl, (C₂~ C₆) -Haloalkenyl, COOR³, COR³, C ONR³R^FourOr-SiR³ ₃And R^FiveR is not hydrogen⁶Is also (C₁~ C₆)- Alkoxy, phenoxy, (C₁~ C₆) -Haloalkoxy, CN, NR³R^FourOr NR³COR^Four Can also be or R^FiveIs R⁶5-or saturated or unsaturated with Can form a 6-membered ring and R³And R^FourHas the above definition,   R⁷Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Alkynyl , Phenyl, (C₁~ C₆) -Alkoxy, pheno Kish, (C₂~ C₆) -Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₃~ C₇) -Shi Chloralkenyloxy, (C₁~ C₆) -Haloalkyl, (C₁~ C₆) -Haloalkoxy, -O H, COOR³, COR³, OCOR³, CONR³R^Four, NR³COR^Four, NR³R^FourOr SiR³ ₃Or R⁷ Is R^FiveOr R⁶Forms a saturated or unsaturated 5- or 6-membered ring with And R³And R^FourHas the definition of claim 2, 3 or 4.     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other Is F, Cl, Br, I, CN or R⁷Has the above definition for R, or R⁷ And R⁸, R⁷And R^TenOr R⁸And R^TenIs saturated or unsaturated 5- or 6- Can be a member of a member ring, and the remaining groups and variables of claim 2 and 3 Or having the definition set forth in 4,   Use according to any one of claims 2-4. 6. R¹Is (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃ ~ C₇) -Cycloalkyl, (C₃~ C₇) -Cycloalkenyl, phenyl, (C₁~ C₆)-Halo Alkyl, (C₂~ C₆) -Haloalkenyl, (C₂~ C₆) -Haloalkynyl, (C₁~ C₆) -Ha Local alkoxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyl oki Si, (C₃~ C₇) -Cycloalkyloxy, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆)- Haloalkenylthio, (C₃~ C₇) -Halocycloalkyl, (C₃~ C₇) -Halocycloal Kenil, (C₃~ C₇) -Halocycloalkoxy, (C₃~ C₇) -Halocycloalkenyl oxy Si, (C₃~ C₇) -Halocycloalkylthio, CN, OH, NO₂, F, Cl, Br, I, CO₂R³ , OCOR³, COR³, NR³COR^Four, NR³R^Four, SO₃R³, SO₂NR³R^Four, Heteroaryl, (up to 5 of each heterocyclic aryl group Carbon atoms and up to 3 identical or different selected from N, S and O Have heteroatoms), and     R³And R^FourHas the definition of claim 2, 3 or 4; Use of compounds. 7. R²Is (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃ ~ C₇) -Cycloalkyl, (C₃~ C₇) -Cycloalkenyl, (C₁~ C₆) -Alkoxy, N-dioxy, (C₁~ C₆) -Alkylthio, phenoxy, phenylthio, (C₂~ C₆)- Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₇~ C₁₃) -Phenylalkoxy Si, (C₇~ C₁₃) -Phenylalkylthio, (C₁~ C₆) -Haloalkyl, (C₁~ C₆)-Halo Alkoxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyloxy , (C₃~ C₇) -Cycloalkyloxy, (C₃~ C₇) -Cycloalkenyloxy, (C₁~ C₆ ) -Haloalkylthio, (C₂~ C₆) -Haloalkenylthio, (C₃~ C₇) -Halocycloa Luquil, (C₃~ C₇) -Halocycloalkenyl, (C₃~ C₇) -Halocycloalkoxy, (C₃ ~ C₇) -Halocycloalkenyloxy, (C₃~ C₇) -Halocycloalkylthio, CO₂R³ , OCOR³, COR³, NR³COR^Four, NR³R^Four, Heteroaryloxy (where heterocyclic ants Each of the aryl groups has up to 5 carbon atoms and 3 selected from N, S and O Up to 4 identical or different heteroatoms), and     R³And R^FourHas the definition of claim 2, 3 or 4.   Use of a compound according to claim 5 or 6. 8. Formula I   [In the formula,     X and R⁷Has the definition of claim 1;     B is a methylene group (which is substituted with an optionally substituted hydroxy Is);     A'is dialkoxyphenyl (wherein the phenyl group is optionally further substituted Is); and     A is halo, cyano, nitro, optionally substituted amino, optionally substituted Selected from alkyl, haloalkoxy, aryl, heterocyclyl Phenyl substituted with one or more groups, where the phenyl group is Are substituted with each other). 9. Whether A is halo, cyano, alkyl, trifluoromethyl and haloalkoxy 9. A compound according to claim 8 which is phenyl substituted with one or more groups selected from Stuff. Ten. Use of the compound according to claim 8 or 9 for eradicating fungi. 11. A fungicidally active amount of at least one compound of formula I according to claim 8 or 9. A fungicidal composition containing the product together with conventional additives and auxiliaries. 12. A fungicidally active amount of at least one compound of formula I according to claim 8 or 9. And preferably fungicides, insecticides, desiccants, sterilizers, acaricides and nematicides. And a few selected from the group of herbicides Contain at least one further active ingredient together with customary additives and auxiliaries Plant protection composition. 13. An active amount of at least one compound of formula I according to claim 8 or 9 As a wood preservative or with paints or paints, containing additives and auxiliaries. Knucker, cooling lubricant for metal processing or for boring and cutting oils For use as a preservative for. 14. 14. Any one of claims 11 to 13 containing at least one surfactant. Composition. 15． As a wood preservative or as paint and thickener, cooling lubricant for metal treatment Is a preservative for boring oil and cutting oil. Use of the compound according to item 1. 16. Phytopathogenic fungi or plants, surfaces or substrates affected by these or Is a fungicidally active amount to seeds, a compound of formula I according to any one of claims 1-8. A method for eradicating phytopathogenic fungi, which comprises applying. 17． A fungicidally active amount of a compound of formula I according to any one of claims 1-8. Having wood preservatives or paints, thickeners, cooling lubricants or bows for metal processing Preservatives for ring and cutting oils. 18. Species treated with a fungicidally active amount of a compound of formula I according to claim 8 or 9. Child.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI A01N 43/76 9450-4H A01N 43/76 55/00 9450-4H 55/00 D 57/14 9450-4H 57 / 14 B C07C 231/02 C07C 231/02 235/36 235/36 235/80 235/80 237/20 237/20 237/22 237/22 255/57 255/57 317/44 7419-4H 317/44 C07D 211/22 9284-4C C07D 211/22 211/76 9284-4C 211/76 213/50 9164-4C 213/50 213/64 9164-4C 213/64 213/79 9164-4C 213/79 263/24 9283-4C 263/24 263/44 9283-4C 263/44 333/06 9455-4C 333/06 C07F 7/10 9450-4H C07F 7/10 D 9/12 9450-4H 9/12 9/40 9450- 4H 9/40 D (81) Designated countries EP (AT, BE, CH, DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE), OA (BF , BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG), AU, BG, BR, CA, CN, CZ, FI, HU, JP, KR, NO, NZ, PL, RO, RU, SD, SK, UA (72) Inventor Sachse, Burghardt Federal Republic of Germany Day 65779 Kerkheim. Andea Twigerei 30

Claims (1)

[Claims] 1. Formula I for eradication of fungi   [In the formula,     A is an optionally substituted aryl group;     A'is an optionally substituted aryl group;     B is a carbonyl or methylene group (which may be an optionally substituted hydroxy group). And optionally further substituted));     X has an optionally substituted alkylene chain having 2 to 4 carbon atoms (wherein Any two substituents on either carbon are oxo or optionally substituted Capable of forming an imino group); and     R⁷Is heterocyclyl, aryl, silyl, alkyl, alkenyl, cyclo Alkyl, alkynyl, cycloalkenyl, amino, hydroxy, mercapto ( Each of these optionally substituted), with hydrogen, cyano or acyl And where B is substituted with an optionally substituted hydroxy, then The substituent on the hydroxy of is R⁷Or with any other substituents on B. Can form a ring together with each other], its stereoisomers and And the use of mixtures thereof. 2. A is of formula II or III   Is a group represented by     A'is of formula IV or V   A group represented by the following formula;     m, n, m'and n'are integers;     m = 1-5;     n = 1 to 7;     m '= 0-5;     n '= 0-7;     R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₈ ) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁~ C₆ ) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Alkyl, (C₁ ~ C₈) -Heteroaryl, (C₁~ C₈) -Non-aromatic heterocyclyl, (C₁~ C₈) -Hete Lower aryl- (C₁~ C₆) -Alkyl, (C₁~ C₈) -Non-aromatic heterocyclyl- (C₁~ C₆) -Alkyl, cyano, nitro, halogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCO R³, -OCOOR³, -OCO-NR³R^Four, -SR³, -SOR³, -SO₂R³, -SO₂-OR³, -SO₂NR³R^Four, -NR³R^Four , -NR³-SO₂R^Four, -NR³-COR^Four, -P (O) (OR³) (OR^Four), -O-P (O) (OR³) (OR^Four) Or-SiR³ ₃ And     In the first 10 of these groups, optionally the following conditions:     a) when 1, 2 or 3 CH-CH- units are present in a non-cyclic state, Each is replaced by 1, 2 or 3 CH = CH-units,     b) 1 CH₂-CH₂-If the unit exists in a non-cyclic state, it is C≡C -Replaced by units,     c) When one CH-CH- unit is present in the ring, it is located by the C≡C- unit Can be exchanged,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O-CO-NR³R^Four, -SR³ , -SOR³, -SO₂R³, -SO₂-OR³, -SO₂-NR³R^Four, -NR³R^Four, -NR³-COR^Four, -P (O) (OR³) (OR^Four ), -O-P (O) (OR³) (OR^Four) And -SiR³ ₃Up to three identical or selected from the group Replaced by different substituents,     e) After substitution by d), the hydrogen atoms remaining on carbon atoms that are not part of the ring are Partially or wholly replaced by the same or different halogen atoms,     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Is hydrogen Up to three identical or different selected from the substituents described in d)) Replaced by the substituent     g) After substitution by f), hydrogen atoms remaining on carbon atoms that are part of the ring Partially or wholly replaced by one or different halogen atoms,     h) one or two of which is present except at the point of attachment of the group CH₂-Units are O, S, CO and NR³The same or different groups selected from the group Be replaced,   At least one of is satisfied;     R³And R^FourAre the same or different and independent of each other, hydrogen, (C₁~ C₁₈) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- ( C₁~ C₆) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- (C₁~ C₆) -Archi Le, (C₁~ C₈) -Heteroaryl or (C₁~ C₈) -Heteroaryl- (C₁~ C₆) -Archi Where in the first seven groups, optionally the following conditions:     a) when 1, 2 or 3 CH-CH- units are present in a non-cyclic state, Each is replaced by 1, 2 or 3 CH = CH-units,     b) 1 CH₂-CH₂-If the unit exists in a non-cyclic state, it is C≡C -Replaced by units,     c) When one CH-CH-unit is present in a ring, it is replaced by a C = C-unit Can be exchanged,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³′, -COOR³′, -CONR³′₂, -OR³′, -OCOR³′, -OCOOR³′, -O-CO -NR³′, -SR³′, -SOR³′, -SO₂R³′, -SO₂-OR³′, -SO₂NR³′₂, -NR³′₂, -NR³ ′ -COR³′, -P (O) (OR³) (OR^Four), -O-P (O) (OR³) (OR^Four) And -SiR³′₃Choose from a group of Replaced by up to 3 identical or different substituents     e) After substitution by d), the hydrogen atoms remaining on carbon atoms that are not part of the ring are Partially formed by the same or different halogen atoms. Or all are replaced,     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Is hydrogen Up to three identical or different selected from the substituents described in d)) Replaced by the substituent     g) After substitution by f), hydrogen atoms remaining on carbon atoms that are part of the ring Partially or wholly replaced by one or different halogen atoms,     h) 1 or 2 CHs present other than at the bonding position of the group₂-Unit is O , S, CO and NR3 ′ replaced by the same or different groups selected Be   At least one of:     R³And R^FourTogether (C₃~ C₆) -Alkylene group (where 1 CH₂-The basis is Optionally replaced by CO-, O, S or NR3 ');     R³′ Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Archi Nil, (C₁~ C₆) -Haloalkyl, (C₂~ C₆) -Haloalkenyl, (C₂~ C₆) -Haloal Quinyl, (C₃~ C₆) -Cycloalkyl, (C₃~ C₆) -Cycloalkyl- (C₁~ C_Four) -Archi Le, (C₆~ C_Ten) -Aryl, (C₇~ C₁₁) -Aralkyl and (C₁~ C_Five) -Heteroary The same or different groups selected from the group of The groups are cyano, nitro, halogen, (C₁~ C_Four) -Alkyl, (C₁~ C_Four) -Haloalkyl, (C₁~ C_Four) -Alkoxy, (C₁~ C_Four) -Haloalkoxy, phenyl, phenoxy, benzene One or two identical or different selected from the group of dil and benzyloxy Can have a substituent in the ring;     B is of formula VI or VII   Is the basis of;     R^FiveIs hydrogen, (C₁~ C₁₈) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Shi Chloalkyl- (C₁~ C₆) -Alkyl, (C₆~ C₁₈) -Aryl, (C₆~ C₁₈) -Aryl- ( C₁~ C₆) -Alkyl, (C₁~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C₆) -Alkyl, cyano, -COR³, -COOR³, -CONR³R^FourOr-SiR³ ₃(Where R³And And R^FourHas the above definition), where in the groups described in the second to the eighth, By R¹And R²At least one of the conditions a) to h) specified for the group Defeated;     R⁶Is hydrogen or R¹With the definition given above for R^Five= With hydrogen R in some cases⁶Is not bonded via an O-, S- or N-atom, or     R^FiveAnd R⁶Together (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is C O, O, S or NR³Optionally replaced by'and / or present One of the CH-CH-units is optionally replaced with a C = C-unit);     R⁷Is hydrogen, or R above except for nitro and halogen.¹Described in Has a sense; or     R^FiveAnd R⁷Together (C₂~ C_Five) -Alkylene group (where 1 CH₂-The base is C O, O, S or NR³Optionally replaced by ' And / or one of the CH-CH-units present is a C = C-unit and optionally Exchanged) and R⁶Has the above definition;     R⁶And R⁷Together (C₃~ C₆) -Alkylene group (where 1 CH₂-The base is C O, O, S or NR³Optionally replaced by'and / or present One of the CH-CH-units is optionally replaced by C = C-units) R^FiveHas the above definition;     X is the formula VIII               -CR⁸R⁹-(CR^TenR¹¹)_p-(VIII) Is the basis of;     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , R⁷Has the definition described above for or is halogen or nitro, And here R⁸And R⁹Or R^TenAnd R¹¹Or together, add an oxo group Can be O by forming, or     R^TenAnd R¹¹Group together = N-OR³Can be formed, or     R⁷And R⁸Together (C₂~ C_Five) -Forming an alkylene group, R⁷And R^TenIs Together (C₁~ C_Four) -Forming an alkylene group or R⁸And R^TenAre together ((C₃~ C₆) -Alkylene groups are formed, in which in each case one CH₂-The base is CO, O, S or NR³C optionally substituted by'and / or present One of the H-CH-units is optionally replaced by a C = C-unit and this ring bond Groups not related to have the above definitions; and     p is 1, 2 or 3;   Use of the compounds according to claim 1 and their salts, especially acid addition salts. 3. R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkyl- (C₁~ C_Four ) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁~ C_Four) -Alkyl, (C₁ ~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C_Four) -Alkyl, shea No, nitro, halogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O CO-NR³R^Four, -SR³, -SOR³, -SO₂R³, -SO₂-OR³, -SO₂NR³R^Four, -NR³R^Four, -NR³-SO₂R^Four, -NR³-COR^FourOr-SiR³ ₃Where, in the first 7 groups, B), c), e), g) and h) as defined above for the groups of     a) When one CH-CH- unit is present in a non-cyclic state, it is CH = CH-replaced by units,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³, -COOR³, -CONR³R^Four, -OR³, -OCOR³, -OCOOR³, -O-CO-NR³R^Four, -SR³ , -SOR³, -SO₂R³, -SO₂-OR³, -SO₂-NR³R^Four, -NR³R^Four, -NR³-COR^FourAnd-SiR³ ₃of Replaced by up to 3 identical or different substituents selected from the group:     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³(R³= Is hydrogen Up to three identical or different selected from the substituents described in d)) At least one of the following is satisfied:     R³And R^FourAre the same or different and independent of each other , (C₁~ C₁₂) -Alkyl, (C₃~ C₈) -Cycloalkyl, (C₃~ C₈)^-Cycloalkyl Le- (C₁~ C_Four) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- (C₁~ C_Four) -A Luquil, (C₁~ C₈) -Heteroaryl or (C₁~ C₈) -Heteroaryl- (C₁~ C_Four) -A Rukiru, and in the last seven groups described here, B), c), e), g) and h) of the above defined conditions and the following conditions:     a) When one CH-CH- unit is present in a non-cyclic state, it is CH = CH-replaced by units,     d) Hydrogen atoms present on carbon atoms that are not part of the ring are cyano, nitro or ha Rogen, -COR³′, -COOR³′, -CONR³′₂, -OR³′, -OCOR³′, -OCOOR³′, -O-CO -NR³′, -SR³′, -SOR³′, -SO₂R³′, -SO₂-OR³′, -SO₂NR³′₂, -NR³′₂, -NR³ ′ -COR³′ And -Si (R³′)₃Up to three identical or different selected from the group of Replaced by a substituent,     f) a hydrogen atom present on a carbon atom which is part of a ring is a group R³′ (R³′ = With hydrogen Up to 3 identical or selected from the substituents described in d)) Replaced by different substituents,   At least one of is satisfied;     R³'And B have the above definitions;     R^FiveIs hydrogen, (C₁~ C₁₂) -Alkyl, (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂) -Shi Chloalkyl- (C₁~ C_Four) -Alkyl, (C₆~ C₁₂) -Aryl, (C₆~ C₁₂) -Aryl- ( C₁~ C_Four) -Alkyl, (C₁~ C₈) -Heteroaryl, (C₁~ C₈) -Heteroaryl- (C₁~ C_Four)- Alkyl, cyano, -COR³, -COOR³, -CONR³R^FourOr SiR³ ₃(Where R³And R^FourIs (With the above definitions), where the 2nd to 8th groups are optionally R¹And R²At least one of the conditions a) to h) specified for the radical of is fulfilled;     R⁶Is hydrogen or R¹With the definition given above for R^Five= With hydrogen R in some cases⁶Is not bonded via an O-, S- or N-atom, or     R^FiveAnd R⁶Forms a ring as defined in claim 2;     R⁷Is hydrogen, or R above except for nitro and halogen.¹Described in Has a sense; or     R^FiveAnd R⁷Forms a ring as defined in claim 2;     R⁶And R⁷Forms a ring as defined in claim 2;     X has the definition of claim 2;     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , R⁷Has the definition described above for or is halogen, and wherein R⁸ And R⁹Or R^TenAnd R¹¹Together again to form an oxo group Can be more O, or     R^TenAnd R¹¹Group together = N-OR³Can be formed, or     R⁷And R⁸, R⁷And R^TenOr R⁸And R^TenIs the ring defined in claim 2 Done;     And the groups not related to this ring bond have the above definitions; and     p has the definition of claim 2,   Use of the compound according to claim 2. 4. R¹And R²Are the same or different and independent of each other, and (C₁~ C₁₂ ) -Alkyl, (C₂~ C₁₂) -Alkenyl, (C₂~ C₁₂) -Alkynyl, (C₆~ C₁₂) -Ant , (C₇~ C₁₃) -Aralkyl, (C₁~ C₁₂) -Alkoxy, (C₂~ C₁₂) -Alkenylo Kish, (C₂~ C₁₂) -Alkynyloxy, (C₁~ C₁₂) -Alkylthio, (C₆~ C₁₂) -Ant Oxy, (C₇~ C₁₃) -Arylalkoxy, (C₇~ C₁₃) -Arylalkylchi Oh, (C₆~ C₁₂) -Arylthio, heteroaryl, heteroaryl- (C₁~ C_Four) -Al Kill, heteroaryloxy, heteroaryl- (C₁~ C_Four) -Alkyloxy, het Lower aryl- (C₁~ C_Four) -Alkylthio, heteroaryloxy- (C₁~ C_Four) -Alkyl (Wherein the heterocyclic aryl group is each up to 8 carbon atoms and N, S and Having up to 4 identical or different heteroatoms selected from O), (C₃~ C₁₂ ) -Cycloalkyl, (C₃~ C₁₂) -Cycloalkoxy, (C₃~ C₁₂) -Cycloalkeni Le, (C₃~ C₁₂) -Cycloalkenyloxy, -CN, OH, NO₂, F, Cl, Br, I, -COO R³, -COR³, -OCOR³, -CONR³R^Four, -R³COR^Four, -NR³R^Four, -SO₂NR³R^Four, -NR³SO₂R^Four, -NR³ COR^Four, -SiR³ ₃, -SO₂R³Or-SO₃R³Where the first 23 groups are defined in Claim 2 or Or optionally substituted by the method described in 3 above,     R³And R^FourHas the definition of claim 2 or 3;     R^FiveAnd R⁶Are independent of each other, hydrogen, (C₁~ C₁₂) -Alkyl, (C₂~ C₁₂)- Alkenyl, (C₂~ C₁₂) -Alkynyl, (C₆~ C₁₂) -Aryl, (C₇~ C₁₂) -Aralchi Le, (C₇~ C₁₂) -Aryloxyalkyl, heteroaryl, heteroaryl- (C₁ ~ C_Four) -A Rualkyl, heteroaryloxy- (C₁~ C_Four) -Alkyl (wherein a heterocyclic aryl group Are each up to 8 carbon atoms and up to 4 carbon atoms selected from N, S and O Having the same or different heteroatoms), (C₃~ C₁₂) -Cycloalkyl, (C₃~ C₁₂ ) -Cycloalkenyl, COOR³, COR³, -CONR³R^FourOr-SiR³ ₃And here is the first The radicals 2-12 are optionally substituted by the process of claims 2 or 3. Cage or R^FiveIs R⁶Together with saturated or unsaturated 5-, 6-, 7- or Can form an 8-membered ring, and R³And R^FourHas the above definition, and R^FiveR is not hydrogen⁶Is also (C₁~ C₆) -Alkoxy, (C₁~ C₆) -Halo arcoki Si, phenoxy, CN, -NR³R^Four, -NR³SO₂R^FourOr-NR³COR^FourCan also be;     R⁷Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Arkini Le, (C₆~ C₁₂) -Aryl, (C₇~ C₁₂) -Alkaryl, (C₁~ C₆) -Alkoxy, (C₂~ C₆) -Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₆~ C₁₂) -Aryloki Si, (C₇~ C₁₃) -Alkaryloxy, heteroaryl, heteroaryl- (C₁~ C_Four)- Alkyl, heteroaryloxy, heteroaryl- (C₁~ C_Four) -Alkyloxy ( Here, the heterocyclic aryl groups are each up to 8 carbon atoms and N, S and O. Having up to 4 identical or different heteroatoms selected from), (C₃~ C₈) -Cycloalkyl, (C₃~ C₈) -Cycloalkoxy, (C₃~ C₈) -Cycloalkenyl, ( C₃~ C₈) -Cycloalkenyloxy, -OH, COOR³, COR³, -OCOR³, CONR³R^Four, NR³CO R^Four, SiR³ ₃Or NR³R^FourWherein the groups described in the above 2nd to 19th groups are Or described in 3 Optionally substituted by the method, and R³And R^FourHas the above definition, and Is R⁷Is R^FiveOr R⁶Part of a saturated or unsaturated 5- or 6-membered ring together with To form;     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other , F, Cl, Br, I, CN or R⁷Has the above definition for, or R⁷And R⁸, R⁷And R^TenOr R⁸And R^TenIs saturated or unsaturated 5- or 6 A part of a-, 7- or 8-membered ring is formed, and the remaining groups and variables are defined in claim 2. Or has the definition described in 3.   Use of a compound according to claim 2 or 3. 5. R¹And R²Are the same or different and independent of each other, and (C₁~ C₆ ) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃~ C₇) -Cycloa Luquil, (C₃~ C₇) -Cycloalkenyl, (C₃~ C₆) -Alkoxy, benzyloxy, (C₁~ C₆) -Alkylthio, phenyl, phenoxy, phenylthio, (C₂~ C₆) -Al Kenyloxy, (C₃~ C₆) -Alkynyloxy, (C₇~ C₁₃) -Phenylalkoxy, ( C₇~ C₁₃) -Phenylalkylthio, (C₁~ C₆) -Haloalkyl, (C₁~ C₆) -Haloal Koxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyloxy, special Fluoroalkyl and fluoroalkoxy, (C₃~ C₇) -Cycloalkyl oki Si, (C₃~ C₇) -Cycloalkenyloxy, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆) -Haloalkenylthio, (C₃~ C₇) -Halocycloalkyl, (C₃~ C₇) -Halocycloa Lucenyl, (C₃~ C₇) -Halocycloalkoxy, (C₃~ C₇) -Halocycloalkenylo Kish, (C₃~ C₇) -Halocycloalkylthio, especially fluoro Alkylthio, CN, OH, NO₂, F, Cl, Br, I, CO₂R³, OCOR³, COR³, NR³COR^Four, NR³R^Four, SO₃R³, SO₂NR³R^Four, Heteroaryl, heteroaryloxy (where Each of the cyclic aryl groups is selected from up to 5 carbon atoms and N, S and O Up to 3 identical or different heteroatoms), and     R³And R^FourHas the above definition;     m = 1-5;     n = 1 to 4;     m ′ = 2-5;     n '= 2-4;     R^FiveAnd R⁶Are the same or different and independent of each other, hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Alkynyl, (C₃~ C₇) -Cycloal Kill, (C₃~ C₇) -Cycloalkenyl, phenyl, heteroaryl (wherein heterocycle The formula aryl groups are each selected from up to 5 carbon atoms and N, S and O Up to 3 identical or different heteroatoms), (C₁~ C₆) -Hydroxy Alkyl, (C₁~ C₆) -Haloalkyl, (C₂~ C₆) -Haloalkenyl, COOR³, COR³, C ONR³R^FourOr-SiR³ ₃And R^FiveR is not hydrogen⁶Is also (C₁~ C₆)- Alkoxy, phenoxy, (C₁~ C₆) -Haloalkoxy, CN, NR³R^FourOr NR³COR^Four Can also be or R^FiveIs R⁶Together with saturated or unsaturated 5-or Can form a 6-membered ring and R³And R^FourHas the above definition,     R⁷Is hydrogen, (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₂~ C₆) -Arkini Le, phenyl, (C₁~ C₆) -Alkoxy, pheno Kish, (C₂~ C₆) -Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₃~ C₇) -Shi Chloralkenyloxy, (C₁~ C₆) -Haloalkyl, (C₁~ C₆) -Haloalkoxy, -O H, COOR³, COR³, OCOR³, CONR³R^Four, NR³COR^Four, NR³R^FourOr SiR³ ₃Or R⁷ Is R^FiveOr R⁶Form a saturated or unsaturated 5- or 6-membered ring with , And R³And R^FourHas the definition of claim 2, 3 or 4.     R⁸, R⁹, R^TenAnd R¹¹Are the same or different and independent of each other Is F, Cl, Br, I, CN or R⁷Has the above definition for R, or R⁷ And R⁸, R⁷And R^TenOr R⁸And R^TenIs saturated or unsaturated 5- or 6 -Can be a member of a ring, and the remaining groups and variables of claim 2 Having the definition set forth in 3 or 4;   Use according to any one of claims 2-4. 6. R¹Is (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃ ~ C₇) -Cycloalkyl, (C₃~ C₇) -Cycloalkenyl, phenyl, (C₁~ C₆)-Halo Alkyl, (C₂~ C₆) -Haloalkenyl, (C₂~ C₆) -Haloalkynyl, (C₁~ C₆) -Ha Local alkoxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyl oki Si, (C₃~ C₇) -Cycloalkyloxy, (C₁~ C₆) -Haloalkylthio, (C₂~ C₆)- Haloalkenylthio, (C₃~ C₇) -Halocycloalkyl, (C₃~ C₇) -Halocycloal Kenil, (C₃~ C₇) -Halocycloalkoxy, (C₃~ C₇) -Halocycloalkenyl oxy Si, (C₃~ C₇) -Halocycloalkylthio, CN, OH, NO₂, F, Cl, Br, I, CO₂R³ , OCOR³, COR³, NR³COR^Four, NR³R^Four, SO₃R³, SO₂NR³R^Four, Heteroaryl, (up to 5 of each heterocyclic aryl group Carbon atoms and up to 3 identical or different selected from N, S and O Have heteroatoms), and     R³And R^FourHas the definition of claim 2, 3 or 4.   Use of the compound according to claim 5. 7. R²Is (C₁~ C₆) -Alkyl, (C₂~ C₆) -Alkenyl, (C₃~ C₆) -Alkynyl, (C₃ ~ C₇) -Cycloalkyl, (C₃~ C₇) -Cycloalkenyl, (C₁~ C₆) -Alkoxy, N-dioxy, (C₁~ C₆) -Alkylthio, phenoxy, phenylthio, (C₂~ C₆)- Alkenyloxy, (C₃~ C₆) -Alkynyloxy, (C₇~ C₁₃) -Phenylalkoxy Si, (C₇~ C₁₃) -Phenylalkylthio, (C₁~ C₆) -Haloalkyl, (C₁~ C₆)-Halo Alkoxy, (C₂~ C₆) -Haloalkenyloxy, (C₃~ C₆) -Haloalkynyloxy , (C₃~ C₇) -Cycloalkyloxy, (C₃~ C₇) -Cycloalkenyloxy, (C₁~ C₆ ) -Haloalkylthio, (C₂~ C₆) -Haloalkenylthio, (C₃~ C₇) -Halocycloa Luquil, (C₃~ C₇) -Halocycloalkenyl, (C₃~ C₇) -Halocycloalkoxy, (C₃ ~ C₇) -Halocycloalkenyloxy, (C₃~ C₇) -Halocycloalkylthio, CO₂R³ , OCOR³, COR³, NR³COR^Four, NR³R^Four, Heteroaryloxy (where heterocyclic ants Each of the aryl groups has up to 5 carbon atoms and 3 selected from N, S and O Up to 4 identical or different heteroatoms), and     R³And R^FourHas the definition of claim 2, 3 or 4.   Use of a compound according to claim 5 or 6. 8. Formula I   [In the formula,     X and R⁷Has the definition of any one of claims 1-7;     B is a methylene group (which is substituted with an optionally substituted hydroxy Is);     A'is dialkoxyphenyl (wherein the phenyl group is optionally further substituted Is); and     A is halo, cyano, nitro, optionally substituted amino, optionally substituted Selected from alkyl, haloalkoxy, aryl, heterocyclyl Phenyl substituted with one or more groups, where the phenyl group is Are substituted with each other). 9. Whether A is halo, cyano, alkyl, trifluoromethyl and haloalkoxy 9. A compound according to claim 8 which is phenyl substituted with one or more groups selected from Stuff. Ten. Use of the compound according to claim 8 or 9 for eradicating fungi. 11. A fungicidally active amount of at least one of the claims 1-8. A fungicidal composition containing a compound of formula I together with conventional additives and auxiliaries. 12. A fungicidally active amount of at least one of the claims 1-8. A compound of formula I and preferably a fungicide, insecticide, At least one selected from the group of desiccants, sterilizers, acaricides, nematicides and herbicides A plant which also contains one further active ingredient together with conventional additives and auxiliaries Protective composition. 13. 9. An active amount of at least one compound of formula I according to any one of claims 1-8. As a wood preservative or paint, containing the product with conventional additives and auxiliaries Or thickeners, cooling lubricants for metal processing or boring oil and cutty A composition for use as a preservative for oil for casting oil. 14. 14. Any one of claims 11 to 13 containing at least one surfactant. Composition. 15． As a wood preservative or as paint and thickener, cooling lubricant for metal treatment Is a preservative for boring oil and cutting oil. Use of the compound according to item 1. 16. Phytopathogenic fungi or plants, surfaces or substrates affected by these or Is a fungicidally active amount to seeds, a compound of formula I according to any one of claims 1-8. A method for eradicating phytopathogenic fungi, which comprises applying. 17． A fungicidally active amount of a compound of formula I according to any one of claims 1-8. Having wood preservatives or paints, thickeners, cooling lubricants or bows for metal processing Preservatives for ring and cutting oils. 18. Treatment with a fungicidally active amount of a compound of formula I according to any one of claims 1-8. Seed to be treated.