CN100567286C

CN100567286C - The fungicidal composition that contains amide derivatives

Info

Publication number: CN100567286C
Application number: CNB2005800273205A
Authority: CN
Inventors: 中村裕治; 三谷滋; 米田哲夫
Original assignee: Ishihara Sangyo Kaisha Ltd
Current assignee: Ishihara Sangyo Kaisha Ltd
Priority date: 2004-08-12
Filing date: 2005-08-10
Publication date: 2009-12-09
Anticipated expiration: 2025-08-10
Also published as: ZA200701243B; CN101001528A

Abstract

Many conventional sterilization compositions have feasible control of actually operating problem or treatment effect deficiency, and residual effect is tended to deficiency, or the control action kou basis of plant disease is used the place and deficiency, so wish to have a kind of fungicidal composition that can overcome these problems.The invention provides a kind of fungicidal composition that contains formula (I) amide derivatives or its salt as activeconstituents, wherein A replaces or unsubstituted phenyl, replacement or unsubstituted benzyl, replacement or unsubstituted naphthyl, replacement or unsubstituted heterocycle, replacement or unsubstituted annelated heterocycles etc.; B replaces or unsubstituted heterocycle, replacement or unsubstituted annelated heterocycles, replacement or unsubstituted naphthyl etc.; Each R ¹And R ²Be alkyl etc. independently of one another; R ³Be hydrogen etc.; W ¹And W ²Be oxygen or sulphur independently of one another.

Description

The fungicidal composition that contains amide derivatives

Invention field

The present invention relates to contain the fungicidal composition of amide derivatives.

Background technology

WO2001/60783 and WO2003/27059 disclose the amide derivatives activeconstituents of used as pesticides with particular chemical structure, but do not have open following formula (I) compound to have fungicidal activity.On the other hand, the applicant's Japanese patent application No.2003-420864 discloses a kind of fungicidal composition that contains amide derivatives as activeconstituents, but the activeconstituents with this composition is different with formula given below (I) compound.

The fungicidal composition of many routines has the actually operating problem makes prevention effect or treatment effect deficiency, residual effect also be tending towards not enough, or the control action kou of opposing plant disease is according to using the place and deficiency.Therefore, need a kind of fungicidal composition that can overcome these problems.

Summary of the invention

The inventor has studied to address the above problem, found that the fungicidal composition that contains formula given below (I) amide derivatives demonstrates the excellence control and the treatment effect of the various various diseases that caused by harmful fungoid of opposing, described fungi for example is phycomycete (Oomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes) or imperfect fungi (Deuteromycetes), and has satisfied especially residual activity simultaneously.Finished the present invention on this basis.

That is to say, the invention provides a kind of fungicidal composition that contains formula (I) amide derivatives or its salt as activeconstituents:

In addition, the invention provides a kind of method of the various diseases of controlling various harmful fungoids or being caused by various harmful fungoids, this method comprises this amide derivatives or its salt that applies significant quantity; Or a kind of cover crop is provided or improves the method for crop yield, this method comprises this amide derivatives or its salt that applies significant quantity.In addition, the invention provides amide derivatives or its salt of formula (I-α), it is former to be unknown:

A wherein^αNot replace or by X^αThe phenyl that replaces, by X^αThe naphthyl that replaces, by X^αThe thienyl that replaces, do not replace or by X^αThe benzo dioxolanyl that replaces, or do not replace or by X^αThe benzodioxan base that replaces; B is the heterocycle (not comprising pyridine radicals) that does not replace or replaced by Y, the annelated heterocycles that does not replace or replaced by Y, or the naphthyl that does not replace or replaced by Y; X^αFluorine, chlorine, iodine, alkyl, haloalkyl, alkoxyalkyl, dialkyl aminoalkyl, alkynyl, the trialkylsilkl alkynyl, hydroxyl, alkoxyl, halogenated alkoxy, the alkoxyl alkoxyl, cycloalkyl, nitro, phenyl, phenyl alkynyl, the pyridine radicals oxygen base that does not replace or replaced by haloalkyl, the alkyl-carbonyl oxygen base, alkyl sulphonyl oxygen base, or heterocycle (described heterocycle can be replaced by halogen, alkyl or alkyl-carbonyl); Y is halogen, replaces or by E¹The alkyl that replaces, do not replace or by E¹The alkenyl that replaces, do not replace or by E¹The alkynyl that replaces, hydroxyl, cyano group oxygen base, do not replace or by E¹The alkoxyl that replaces, do not replace or by E¹The alkenyl oxy that replaces, do not replace or by E¹The alkynyloxy group that replaces, sulfydryl, the cyano group sulfenyl, do not replace or by E¹The alkyl sulfenyl that replaces, do not replace or by E¹The alkenyl thio that replaces, do not replace or by E¹The alkynyl sulfenyl that replaces, do not replace or by E²The alkyl sulfinyl that replaces, do not replace or by E²The alkyl sulphonyl that replaces, do not replace or by the cycloalkyl that J replaces, and do not replace or by the cycloalkyl oxy that J replaces, the cycloalkyl sulfenyl that does not replace or replaced by J, cyano group, nitro, formoxyl ,-OR⁴，-SR ⁵，-NR ⁶R ⁷， -CO ₂R ⁸，-C(＝O)NR ⁸R ⁹，-SO ₂NR ⁸R ⁹，-CH＝NR ¹⁰, or heterocycle (described heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); R¹And R²Hydrogen independently of one another, alkyl, haloalkyl, hydroxy alkyl, alkoxyalkyl, halogenated alkoxy alkyl, cyano group alkyl, alkoxy carbonyl alkyl, alkenyl, halogenated alkenyl, alkoxy alkenyl, alkynyl, halo alkynyl, alkoxyl alkynyl, cycloalkyl, halogenated cycloalkyl, (alkyl) cycloalkyl, (haloalkyl) cycloalkyl, cyano group, or-CO₂R ⁸, perhaps R¹And R²Can form together 3-6 unit saturated carbon ring; R³Be hydrogen, replace or by E¹The alkyl that replaces, do not replace or by E¹The alkenyl that replaces, do not replace or by E¹The alkynyl that replaces, hydroxyl, cyano group oxygen base, do not replace or by E¹The alkoxyl that replaces, do not replace or by the cycloalkyl that J replaces, and do not replace or by the cycloalkyl oxy that J replaces, the cycloalkyl sulfenyl that does not replace or replaced by J, cyano group, formoxyl ,-C (=W³)R ¹¹，-C(＝W ³)OR ¹²，-C(＝W ³)SR ¹²，-C(＝W ³)NR ¹²R ¹³， -S(O)mR ¹², or S (O) nNR¹²R ¹³；R ⁴Be-C (=W³)R ¹²，-C(＝W ³)OR ¹²， -C(＝W ³)SR ¹²，-C(＝W ³)NR ¹²R ¹³，-S(O)mR ¹²，-S(O)nNR ¹²R ¹³, or heterocycle (heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); R⁵Be-C (=W³)R ¹²，-C(＝W ³)OR ¹²，-C(＝W ³)SR ¹²， -C(＝W ³)NR ¹²R ¹³, or heterocycle (heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); R⁶Hydrogen, alkyl, haloalkyl, alkoxyalkyl, halogenated alkoxy alkyl, cyano group alkyl, (cycloalkyl) alkyl, cycloalkyl, cyano group ,-C (=W³)R ¹²，-C(＝W ³)OR ¹²，-C(＝W ³)SR ¹²，-C(＝W ³)NR ¹²R ¹³， -S(O)mR ¹²，-S(O)nNR ¹²R ¹³, or heterocycle (described heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); R⁷Hydrogen, alkyl, haloalkyl, alkoxyalkyl, or halogenated alkoxy alkyl; R⁸And R⁹Hydrogen independently of one another, alkyl, haloalkyl, alkoxyalkyl, or halogenated alkoxy alkyl, and contiguous R⁸And R⁹Can form together ring; R¹⁰It is alkyl (described alkyl can be replaced by halogen, alkoxyl or halogenated alkoxy), alkoxyl (described alkoxyl can be replaced by halogen, alkoxyl or halogenated alkoxy), alkenyl oxy (alkenyl oxy can be replaced by halogen, alkoxyl or halogenated alkoxy) alkynyloxy group (alkynyloxy group can be replaced by halogen, alkoxyl or halogenated alkoxy), or alkoxy carbonyl (alkoxy carbonyl can be replaced by halogen, alkoxyl or halogenated alkoxy); R¹¹Be hydrogen, replace or by E³The alkyl that replaces, phenyl (phenyl can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl), or heterocycle (heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); R¹²And R¹³Not replace or by E independently of one another³The alkyl that replaces, alkoxyl, halogenated alkoxy, the cycloalkyl that does not replace or replaced by J, or phenyl (phenyl can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl), and contiguous R¹²And R¹³Can form together ring; W¹、W ²And W³Oxygen or sulphur independently of one another; M and n are the integer of 0-2 independently of one another; E¹Halogen, hydroxyl, alkoxyl, halogenated alkoxy, sulfydryl, alkyl sulfenyl, haloalkyl sulfenyl, alkyl sulphonyl, cycloalkyl, amino, alkyl monosubstituted amino, dialkyl amido, cyano group, nitro, hydroxycarbonyl group, alkoxy carbonyl, the alkyl-carbonyl oxygen base, trialkylsilkl, or heterocycle (heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); E²Halogen, hydroxyl, alkoxyl, halogenated alkoxy, cycloalkyl, amino, alkyl monosubstituted amino, dialkyl amido, cyano group, nitro, hydroxycarbonyl group, alkoxy carbonyl, trialkylsilkl, or heterocycle (heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); E³Halogen, alkoxyl, alkyl sulfenyl, amino, alkyl monosubstituted amino, dialkyl amido, cycloalkyl, cyano group, alkoxy carbonyl, halogenated alkoxy, haloalkyl sulfenyl, or phenyl (phenyl can be replaced by halogen, alkyl, haloalkyl, alkoxyl, halogenated alkoxy or alkyl-carbonyl); With J be halogen, alkyl, haloalkyl, alkoxyl, or halogenated alkoxy.

In following formula (I), the number of contained substituent X can be 1 or more and under greater than 1 situation in A, and these substituting groups can be identical or different.As contained 2 in A, the substituting group on 3-indanyl or the tetralyl, the number of halogen, alkyl or alkoxyl group can be 1 or more and under greater than 1 situation, and these substituting groups can be identical or different.The number of contained substituting group Y can be 1 or more and under greater than 1 situation in B or X, and these substituting groups can be identical or different.At X, Y, R ³, R ¹¹, R ¹²Or R ¹³In contained substituting group E ¹, E ²Or E ³Number can be 1 or more and under greater than 1 situation, these substituting groups can be identical or different.At X, Y, R ³, R ¹²Or R ¹³In the number of contained substituting group J can be 1 or more and under greater than 1 situation, these substituting groups can be identical or different.As at X, Y, R ⁴, R ⁵, R ⁶, R ¹¹, R ¹², R ¹³, E ¹, E ²Or E ³In contained phenyl or the substituting group on the heterocycle, the number of halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy or alkyl-carbonyl can be 1 or more and under greater than 1 situation, these substituting groups can be identical or different.As at R ¹⁰In substituting group on contained alkyl, alkoxyl group, alkenyloxy, alkynyloxy group or the alkoxy carbonyl, the number of halogen, alkoxyl group or halogenated alkoxy can be 1 or more and under greater than 1 situation, these substituting groups can be identical or different.

At A, B, X, Y, R ⁴, R ⁵, R ⁶, R ¹¹, E ¹Or E ²In heterocycle preferably contain the 3-, the 5-that are selected from 1-4 at least a among O, S and a N atom or 6-unit heterocycle, can be for example 3 yuan of heterocycles, for example Oxyranyles; 5 yuan of heterocycles, furyl for example, tetrahydrofuran base, thienyl, pyrryl, pyrrolinyl, pyrrolidyl, dioxolanyl oxazolyl ， isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, imidazolidyl, pyrazolyl, pyrazolinyl, pyrazolidyl, triazolyl, 4-oxadiazole base, thiadiazolyl group or tetrazyl; 6 yuan of heterocycles, pyranyl for example, pyridyl, piperidyl ， alkyl dioxin ， oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrimidyl, pyrazinyl, piperazinyl or triazinyl.

Annelated heterocycles in A or B preferably contains and is selected from O, the 8-10 of 1-4 at least a atom unit annelated heterocycles among S and the N can be a benzofuryl for example, isobenzofuran-base, dihydro benzo furyl, dihydroisobenzofuran base, benzothienyl, isobenzo-thienyl, dihydrobenzo thienyl, dihydro isobenzo-thienyl, the tetrahydro benzo thienyl, indyl, pseudoindoyl benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl-, benzo dioxolanyl, benzodioxan base, benzopyranyl, chromanyl, isochroman base, the chromone base, chromanone base (chromanonyl), quinolyl, isoquinolyl, cinnolinyl, 2, the 3-phthalazinyl, quinazolyl, quinoxalinyl, the indolizine base, quinolizinyl, imidazopyridyl, 1, the 5-phthalazinyl, pteridyl, Er hydrogen benzoxazinyl, two hydrogen benzoxazole quinoline bases, two hydrogen benzoxazine ketone groups or benzene and thioxane base.

At A, X, Y, R ¹To R ³, R ⁶To R ¹³, E ¹To E ³Or the alkyl among the J or alkyl structure part can be straight chain or branching, for example C _1-7Alkyl, for example methyl, ethyl, propyl group, sec.-propyl, butyl, the tertiary butyl, amyl group, hexyl or heptyl.

At X, Y, R ¹To R ³, R ⁶, R ¹², R ¹³Or E ¹To E ³In cycloalkyl or cycloalkyl structure division can have 3-6 carbon atom, for example cyclopropyl, cyclopentyl or cyclohexyl.In addition, R wherein ¹And R ²The object lesson of the 3-6 unit saturated carbon ring that can form together can be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

At X, Y, R ¹To R ³Or R ¹⁰In alkenyl or alkenyl structure part can be straight chain or the branching group with 2-7 carbon atom, for example vinyl, 1-propenyl, allyl group, pseudoallyl, 1-butylene base, 1,3-butadiene base, 1-hexenyl or 1-heptenyl.In addition, at X, Y, R ¹To R ³Or R ¹⁰In alkynyl or alkynyl structure division can be straight chain or branching group with 2-7 carbon atom, for example ethynyl, 2-butyne base, valerylene base, 3-hexin base or 4-dimethyl-valerylene base.

At A, X, Y, R ¹To R ¹³, E ¹To E ³Or the halogen among the J or can be fluorine, chlorine, bromine or iodine atom as substituent halogen.Number as substituent halogen can be 1 or more, and under greater than 1 situation, these halogens can be identical or different.In addition, these halogens can replace in any position.

Substituent A in above-mentioned formula (I-α) ^αOr X ^αDefinition meet substituent A in above-mentioned formula (I) or the definition of X respectively.

The salt of the amide derivatives of above-mentioned formula (I) or (I-α) can be any salt, and is upward acceptable as long as it is an agricultural.For example, it can be an an alkali metal salt, for example sodium salt or sylvite; Alkaline earth salt, for example magnesium salts or calcium salt; Inorganic acid salt, for example hydrochloride, perchlorate, vitriol or nitrate; Or organic acid salt, for example acetate or mesylate.

The amide derivatives of above-mentioned formula (I) or (I-α) has various isomer, for example optically active isomer or geometrical isomer, and the present invention includes this two kinds of isomer and these mixture of isomers.In addition, the present invention also is included in the interior various isomer except that above-mentioned isomer of well known range of correlative technology field.In addition, according to the type of isomer, they can have and above-mentioned formula (I) or (I-α) different chemical structure, but they within the scope of the invention, because to those skilled in the art, they obviously belong to isomer.

The amide derivatives of above-mentioned formula (I) or (I-α) or its salt can prepare by following reaction (A) to (K), (U) to (W), or by producing the ordinary method preparation of salt.

Reaction (A)

In reaction (A), A, B, R ¹And R ²As above definition.Z is hydroxyl, alkoxy or halogen, and halogen can be fluorine, chlorine, bromine or iodine atom.

Reaction (A) can be carried out in the presence of alkali and solvent usually.

Alkali can be suitably to be selected from following one or more: for example basic metal, for example sodium or potassium; Basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Carbonate, for example yellow soda ash or salt of wormwood; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide; Metal hydride, for example sodium hydride or potassium hydride KH; Amine, for example single methylamine, dimethylamine or triethylamine; Pyridine, for example pyridine or 4-dimethylaminopyridine; And organolithium, for example lithium methide, n-Butyl Lithium or diisopropylaminoethyl lithium.The consumption of alkali can be the 1-3 mole, and preferred 1-2 mole is by every mole of formula (II) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, pyridine, acetonitrile or propionitrile; And ketone, for example acetone or methylethylketone.

If necessary, reaction (A) can be carried out in the presence of dehydrating condensation agent.Dehydrating condensation agent can for example be N, N '-dicyclohexylcarbodiimide, isocyanic acid chloro alkylsulfonyl ester, N, N '-carbonyl dimidazoles and trifluoroacetic anhydride.

Normally 0-100 ℃ of the temperature of reaction of reaction (A), preferred 0-50 ℃, and normally 0.5-48 hour reaction times, preferred 1-24 hour.

Reaction (B)

In reaction (B), A, B, R ¹And R ²As above definition, R ^3aBe not replace or by E ¹The alkyl that replaces does not replace or by E ¹The alkenyl that replaces does not replace or by E ¹The alkynyl that replaces, hydroxyl, cyano group oxygen base does not replace or by E ¹The alkoxyl group that replaces does not replace or by the cycloalkyl that J replaces, and does not replace or by the cycloalkyl oxy that J replaces, the cycloalkyl sulfenyl that does not replace or replaced by J, cyano group, formyl radical ,-C (=W ³) R ¹¹,-C (=W ³) OR ¹²,-C (=W ³) SR ¹²,-C (=W ³) NR ¹²R ¹³,-S (O) mR ¹²Or S (O) nNR ¹²R ¹³(E ¹, J, R ¹¹, R ¹², R ¹³, W ³, m and n as defined above), T is a halogen, described halogen can be fluorine, chlorine, bromine or iodine atom.

Reaction (B) can be carried out in the presence of alkali and solvent usually.

Alkali can be suitably to be selected from following one or more: for example basic metal, for example sodium or potassium; Basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Carbonate, for example yellow soda ash or salt of wormwood; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide; Metal hydride, for example sodium hydride or potassium hydride KH; Amine, for example single methylamine, dimethylamine or triethylamine; And pyridine, for example pyridine or 4-dimethylaminopyridine.The consumption of alkali can be the 1-3 mole, and preferred 1-1.5 mole is by every mole of formula (I-1) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; And ketone, for example acetone or methylethylketone.

Normally 0-100 ℃ of the temperature of reaction of reaction (B), preferred 0-50 ℃, and normally 1-300 hour reaction times, preferred 1-150 hour.

Reaction (C)

In reaction (C), A, R ¹And R ²As defined above, B ¹By-CO ₂Heterocycle or quilt-CO that H replaces ₂The annelated heterocycles that H replaces. formula V is the anhydrous dicarboxylic acid (phenyl, heterocycle or annelated heterocycles) of Q.

Reaction (C) can be carried out in the presence of solvent usually.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; And alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol.

If necessary, reaction (C) can be carried out in the presence of alkali.Alkali can be suitably to be selected from following one or more: for example basic metal, for example sodium or potassium; Basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Carbonate, for example yellow soda ash or salt of wormwood; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide; Metal hydride, for example sodium hydride or potassium hydride KH; Amine, for example single methylamine, dimethylamine or triethylamine; And pyridine, for example pyridine or 4-dimethylaminopyridine.The consumption of alkali can be the 1-3 mole, and preferred 1-1.5 mole is by every mole of formula (II) compound.

Normally 0-150 ℃ of the temperature of reaction of reaction (C), preferred 0-80 ℃.Normally 0.5-96 hour reaction times, preferred 1-48 hour.

Reaction D

In reaction (D), A, R ¹And R ²As defined above.B ²By Y ²The heterocycle that replaces or by Y ²The annelated heterocycles that replaces, B ³By Y ³The heterocycle that replaces or by Y ³The annelated heterocycles that replaces, Y ²Be chlorine, bromine or iodine atom, Y ³It is unsaturated heterocycle (described unsaturated heterocycle can be replaced by halogen, alkyl, haloalkyl, alkoxyl group or halogenated alkoxy).

Reaction (D) can be carried out in the presence of catalyzer, alkali, solvent and rare gas element usually.

Catalyzer can be suitably to be selected from following one or more: palladium complex, for example tetrakis triphenylphosphine palladium (0), two (dibenzalacetone) palladium (0) and three (dibenzalacetones), two palladiums (0).

Alkali can be suitably to be selected from following one or more: for example carbonate, for example yellow soda ash, salt of wormwood or lime carbonate; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide.The consumption of alkali can be the 1-20 mole, and preferred 1-10 mole is by every mole of formula (I-4) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; And water.

Rare gas element can for example be nitrogen or argon gas.

Normally 0-150 ℃ of the temperature of reaction of reaction (D), preferred 15-100 ℃.Normally 0.5-96 hour reaction times, preferred 1-48 hour.

Reaction E

In reaction (E), A, R ¹And R ²As defined above, B ⁴By-CO ₂Heterocycle or quilt-CO that H replaces ₂The annelated heterocycles that H replaces, B ⁵By-CO ₂R ^8aThe heterocycle or the quilt-CO that replace ₂R ^8aThe annelated heterocycles that replaces, R ^8aBe alkyl, haloalkyl, alkoxyalkyl or halogenated alkoxy alkyl.

The first step in reaction (E) can be carried out in the presence of chlorizating agent.Chlorizating agent can be suitably to be selected from following one or more: for example thionyl chloride, oxalyl chloride or phosphorous pentachloride.

If necessary, the first step in the reaction (E) can be carried out in the presence of solvent.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; And ester, for example methyl acetate or ethyl acetate.

Normally 0-200 ℃ of the temperature of reaction of the first step in the reaction (E), preferred 15-150 ℃.Normally 0.1-72 hour reaction times, preferred 0.5-3 hour.

If necessary, second step in the reaction (E) can carry out in the presence of alkali.Alkali can be suitably to be selected from following one or more: for example basic metal, for example sodium or potassium; Basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Carbonate, for example yellow soda ash or salt of wormwood; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide; Metal hydride, for example sodium hydride or potassium hydride KH; Amine, for example single methylamine, dimethylamine or triethylamine; And pyridine, for example pyridine or 4-dimethylaminopyridine.The consumption of alkali can be the 1-5 mole, and preferred 1-2 mole is by every mole of formula (I-6) compound.

If necessary, second step in the reaction (E) can carry out in the presence of solvent.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone.In addition, in this reaction, formula (VII) compound also can be used as solvent when excessive use.

Normally 0-100 ℃ of the temperature of reaction in second step in the reaction (E), preferred 0-50 ℃.Normally 0.1-48 hour reaction times, preferred 0.5-6 hour.

Reaction F

In reaction (F), A, B ⁴, B ⁵, R ¹, R ²And R ^8aAs defined above.

Reaction (F) can be carried out in the presence of catalyzer and dehydrating condensation agent usually.

Catalyzer can be suitably to be selected from following one or more: mineral acid, for example hydrochloric acid or sulfuric acid; Organic acid, for example tosic acid; And Lewis acid, for example boron trifluoride etherate.

Dehydrating condensation agent can be suitably to be selected from following one or more: N for example, N '-dicyclohexylcarbodiimide, isocyanic acid chloro alkylsulfonyl ester, N, N '-carbonyl dimidazoles and trifluoroacetic anhydride.

If necessary, reaction (F) can be carried out in the presence of solvent.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; And alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol.In addition, in this reaction, formula (VII) compound also can be used as solvent when excessive use.

Normally 0-200 ℃ of the temperature of reaction of reaction (F), preferred 0-100 ℃.Normally 0.1-96 hour reaction times, preferred 0.5-24 hour.

Reaction G

In reaction (G), A, B ⁴, R ¹, R ², R ⁸And R ⁹As defined above, B ⁶By-CONR ⁸R ⁹The heterocycle or the quilt-CONR that replace ⁸R ⁹The annelated heterocycles that replaces (R wherein ⁸And R ⁹As defined above).

The first step in the reaction (G) can be carried out according to the first step in the above-mentioned reaction (E).

If necessary, second step in the reaction (G) can carry out in the presence of alkali.Alkali can be suitably to be selected from following one or more: for example basic metal, for example sodium or potassium; Basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Carbonate, for example yellow soda ash or salt of wormwood; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide; Metal hydride, for example sodium hydride or potassium hydride KH; Amine, for example single methylamine, dimethylamine or triethylamine; And pyridine, for example pyridine or 4-dimethylaminopyridine.The consumption of alkali can be the 1-10 mole, and preferred 1-2 mole is by every mole of formula (I-6) compound.

If necessary, second step in the reaction (G) can carry out in the presence of solvent.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; And water.

Normally 0-100 ℃ of the temperature of reaction in second step in the reaction (G), preferred 0-50 ℃.Normally 0.1-48 hour reaction times, preferred 0.5-6 hour.

Reaction H

In reaction (H), A, B ⁴, B ⁶, R ¹, R ², R ⁸And R ⁹As defined above.

Reaction (H) can be carried out in the presence of dehydrating condensation agent and solvent usually.

Normally 0-200 ℃ of the temperature of reaction of reaction (H), preferred 0-100 ℃.Normally 0.1-96 hour reaction times, preferred 0.5-24 hour.

Reaction I

In reaction (I), A, B ⁵, B ⁶, R ¹, R ², R ⁸And R ⁹As defined above.

Reaction (I) can be carried out in the presence of solvent usually.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; And water.In addition, in this reaction, formula (VIII) compound also can be used as solvent when excessive use.

Normally 0-150 ℃ of the temperature of reaction of reaction (I), preferred 0-80 ℃.Normally 0.1-48 hour reaction times, preferred 0.5-24 hour.

Reaction J

In reaction (J), B as defined above; A ¹By-OR ⁴The phenyl that replaces, quilt-OR ⁴The benzyl that replaces, quilt-OR ⁴The naphthyl that replaces, quilt-OR ⁴The heterocycle or the quilt-OR that replace ⁴The annelated heterocycles that replaces (R wherein ⁴As defined above); A ²Be-the substituted phenyl of OH the benzyl that quilt-OH replaces, the naphthyl that quilt-OH replaces, the annelated heterocycles that heterocycle that quilt-OH replaces or quilt-OH replace; R ^1aAnd R ^2aEach is alkyl naturally, haloalkyl, hydroxyalkyl, alkoxyalkyl, halogenated alkoxy alkyl, cyano group alkyl, alkoxy carbonyl alkyl, alkenyl, halogenated alkenyl, alkoxy alkenyl, alkynyl, halo alkynyl, the alkoxyl group alkynyl, cycloalkyl, halogenated cycloalkyl, (alkyl) cycloalkyl, (haloalkyl) cycloalkyl or cyano group, and R ^1aAnd R ^2aCan form 3-6 unit saturated carbon ring together; M is sodium or potassium.

Reaction (J) can be carried out in the presence of solvent usually.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; And water.

Normally 0-100 ℃ of the temperature of reaction of reaction (J), preferred 20-80 ℃.Normally 0.1-24 hour reaction times, preferred 0.1-12 hour.

Reaction K

In reaction (K), A ¹, A ², B, R ^1a, R ^2aAnd R ⁴As defined above, G is chlorine, bromine or iodine atom.

Reaction (K) can be carried out in the presence of alkali and solvent usually.

Alkali can be suitably to be selected from following one or more: for example basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Carbonate, for example yellow soda ash or salt of wormwood; Supercarbonate, for example sodium bicarbonate or saleratus; Metal hydroxides, for example sodium hydroxide or potassium hydroxide; Metal hydride, for example sodium hydride or potassium hydride KH; Amine, for example single methylamine, dimethylamine or triethylamine; And pyridine, for example pyridine or 4-dimethylaminopyridine.The consumption of alkali can be the 1-2 mole, and preferred 1-1.5 mole is by every mole of formula (I-10) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone.

The temperature of reaction of reaction (K) is normally-20 to 100 ℃, preferred 0-50 ℃.Normally 0.1-24 hour reaction times, preferred 0.1-12 hour.

Formula (II) compound of will be in above-mentioned reaction (A) or using (C) can prepare by following reaction (L) to (N).

Reaction (L)

In reaction (L), A, R ¹And R ²As defined above.In reaction (L), the salt of compound (II) can be by the aftertreatment of described reaction or according to the popular response preparation that is used to form salt.

Reaction (L) can be carried out in the presence of oxygenant and solvent usually.

Oxygenant can for example be the Tripotassium iron hexacyanide.The consumption of oxygenant can be the 1-10 mole, and preferred 1-5 mole is by every mole of formula (XII) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: ether, for example diox, tetrahydrofuran (THF) ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, pyridine, acetonitrile or propionitrile; Ketone, for example acetone or methylethylketone.

Normally 20-150 ℃ of the temperature of reaction of reaction (L), preferred 50-100 ℃.Normally 0.5-30 hour reaction times, preferred 1-20 hour.

Reaction (M)

In reaction (M), A, R ¹And R ²As defined above.In reaction (M), the salt of compound (II) can be by the aftertreatment of described reaction or according to the popular response preparation that is used to form salt.

Cyclization in reaction (M) can carry out in the presence of alkali and solvent usually.

Alkali can be suitably to be selected from following one or more: for example basic metal, for example sodium or potassium; Basic metal alcoxylates, for example sodium methylate, sodium ethylate or potassium tert.-butoxide; Metal hydride, for example sodium hydride or potassium hydride KH.The consumption of alkali can be the 1-3 mole, and preferred 1-1.5 mole is by every mole of formula (XIII) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide.

Normally 0-150 ℃ of the temperature of reaction of the cyclization in the reaction (M), preferred 30-100 ℃.Normally 0.5-24 hour reaction times, preferred 1-12 hour.

Hydrolysis reaction in reaction (M) can carry out according to the hydrolysis reaction of routine, and can carry out in the presence of acid or alkali and solvent usually.

Acid can for example be hydrochloric acid or sulfuric acid.Alkali can for example be metal hydroxides, for example sodium hydroxide or potassium hydroxide.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; Nitrile, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone; And water.

Normally 0-100 ℃ of the temperature of reaction of the hydrolysis reaction in the reaction (M), preferred 20-80 ℃.Normally 0.1-12 hour reaction times, preferred 0.1-1 hour.

Reaction (N)

In reaction (N), A, R ¹And R ²As defined above.In reaction (N), the salt of compound (II) can be by the aftertreatment of described reaction or according to the popular response preparation that is used to form salt.

In the reduction reaction of reaction in (N) can for example be catalytic reduction reaction, reduces (for example sodium borohydride or lithium aluminum hydride) by metal hydride; Reduce by for example triphenylphosphine, dimethyl sulphide or phenylbenzene sulphur; Or in the reaction system that constitutes by metal (for example iron or copper) and carboxylic acid (for example formic acid or acetate), reduce.Catalytic reduction is undertaken by the use catalyzer in nitrogen atmosphere usually, and catalyzer for example is platinum, platinum oxide, platinum black, Raney nickel, palladium, palladium-carbon, rhodium or rhodium-aluminium.

Reaction (N) can be carried out in the presence of solvent usually.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene, toluene or dimethylbenzene; Aliphatic hydrocrbon, for example hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, pyridine, acetonitrile or propionitrile; Ketone, for example acetone or methylethylketone; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; And water.

Normally 0-150 ℃ of the temperature of reaction of reaction (N), preferred 0-80 ℃.Normally 0.5-96 hour reaction times, preferred 1-48 hour.

Formula (XIII) compound that will use in above-mentioned reaction (M) can prepare by following reaction (O).

Reaction (O)

In reaction (O), A, R ¹And R ²As defined above.

If necessary, reaction (O) can be carried out in the presence of solvent.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; Polar aprotic solvent, for example acetonitrile, propionitrile or vinyl cyanide; Ketone, for example acetone or methylethylketone.

The consumption of the methyl-iodide in the reaction (O) can be the 1-10 mole, and preferred 1-3 mole is by every mole of formula (XV) compound.In addition, if excessive use, methyl-iodide also can be used as solvent.

Normally 0-100 ℃ of the temperature of reaction of reaction (O), preferred 10-50 ℃.Normally 0.5-48 hour reaction times, preferred 1-24 hour.

Formula (XIV) compound that will use in above-mentioned reaction (N) can prepare by following reaction (P).

Reaction (P)

In reaction (P), A, R ¹And R ²As defined above, U is the chlorine or bromine atom.

Reaction (P) can be carried out in the presence of the azide agent.The azide agent can suitably be to be selected from following one or more: for example sodiumazide, potassium azide and azide trimethyl silyl.

Reaction (P) can be carried out in the presence of solvent usually.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: for example aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone, pyridine, acetonitrile or propionitrile; Ketone, for example acetone or methylethylketone; Alcohol, for example methyl alcohol, ethanol, propyl alcohol or the trimethyl carbinol; And water.

Normally 0-150 ℃ of the temperature of reaction of reaction (P), preferred 20-90 ℃.Normally 0.1-96 hour reaction times, preferred 0.5-12 hour.

Formula (XV) compound that will use in above-mentioned reaction (O) can prepare by following reaction (Q).

Reaction (Q)

In reaction (Q), A, R ¹And R ²As defined above.

Reaction (Q) can be carried out and if necessary, carry out in the presence of dewatering agent and/or catalyzer according to the hydrazone building-up reactions of routine.

As dewatering agent, can for example mention molecular sieve.The consumption of dewatering agent normally formula (XII) compound weight 1-30 doubly, preferred 5-10 is doubly.

Catalyzer can for example be a titanium tetrachloride.

The consumption 1-30 mole normally that is used for the dimethylhydrazine of reaction (Q), preferred 5-10 mole is by every mole of formula (XII) compound.

Normally 20-150 ℃ of the temperature of reaction of reaction (Q), preferred 50-120 ℃.Normally 5-200 hour reaction times, preferred 24-120 hour.

Formula (XVI) compound that will use in above-mentioned reaction (P) can prepare by following reaction (R).

Reaction (R)

In reaction (R), A, R ¹, R ²With U as defined above.

Reaction (R) can be carried out in the presence of chlorizating agent or bromizating agent.Chlorizating agent can be suitably to be selected from following one or more: for example chlorine or N-chlorosuccinimide.Bromizating agent can be suitably to be selected from following one or more: for example bromine, N-bromosuccinimide and phenyl trimethylammonium tribromide ammonium.

Reaction (R) can be carried out in the presence of solvent usually.Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene; Ether, for example diox, tetrahydrofuran (THF), ether or glycol dimethyl ether; Ester, for example methyl acetate or ethyl acetate; Polar aprotic solvent, for example dimethyl sulfoxide (DMSO), tetramethylene sulfone, N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone or pyridine; Organic acid, for example acetate or propionic acid; And water.

If necessary, reaction (R) can be carried out in the presence of alkali or acid.

Alkali can for example be the diisopropylaminoethyl lithium.The consumption of alkali can be the 1-2 mole, and preferred 1-1.2 mole is by every mole of formula (XII) compound.

When carrying out under the existence that is reflected at alkali, solvent can normally suitably be selected from following one or more: ether, for example tetrahydrofuran (THF) and ether.

Acid can normally suitably be selected from following one or more: organic acid for example, for example acetate or propionic acid, and aluminum chloride.The consumption of acid is catalytic amount normally.In addition, if during excessive use, can be as the organic acid of solvent not only as solvent but also as acid.

The temperature of reaction of reaction (R) is normally-100 to 150 ℃, preferred-78 to 110 ℃.Normally 0.1-48 hour reaction times, preferred 0.5-24 hour.But, if being reflected under the existence of alkali, this carries out, then temperature of reaction is normally-100 to 0 ℃, and preferred-78 to-20 ℃, normally 0.1-12 hour reaction times, preferred 0.5-6 hour.Carry out if this is reflected under the sour existence, then temperature of reaction is normally 0-150 ℃, and preferred 20-110 ℃, normally 0.1-48 hour reaction times, preferred 1-24 hour.

Compound (XII) compound that will use in above-mentioned reaction (Q) is known compound, maybe can be by following reaction (S) to (T) or according to corresponding method preparation.

Reaction (S)

In reaction (S), R ¹And R ²As defined above, Z be Sauerstoffatom or-C (G ¹) G ², X ^aBe hydrogen atom, chlorine atom or alkyl, X ^a' be chlorine atom or alkyl, X ^b, X ^c, X ^d, X ^e, G ¹And G ²Each is hydrogen, fluorine or chlorine atom naturally, and V is the bromine or iodine atom, and j is 0 or 1.

The first step in the reaction (S) can be carried out in the presence of alkali and solvent.

Alkali can suitably be selected from organolithium compound, for example diisopropylaminoethyl lithium.The consumption of alkali can be the 1-2 mole, and preferred 1-1.5 mole is by every mole of formula (XVII-1) or formula (XVII-2) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: ether, for example diox, tetrahydrofuran (THF) and ether.

The chlorizating agent that is used for reacting (S) the first step can for example be a N-chlorosuccinimide.

Used formula: X in the first step of reaction (S) ^aThe consumption of '-I is the 1-10 mole, and preferred 1-5 mole is by every mole of formula (XVII-1) or formula (XVII-2) compound.In addition, the consumption of used chlorizating agent is the 1-5 mole in the first step of reaction (S), and preferred 1-3 mole is by every mole of formula (XVII-1) or formula (XVII-2) compound.

If necessary, the first step of reaction (S) can be carried out in the presence of rare gas element.Rare gas element can suitably be selected from for example nitrogen or argon gas.

The temperature of reaction of the first step of reaction (S) is normally-100 to 50 ℃, preferred-70 to 25 ℃.Normally 1-48 hour reaction times, preferred 1-20 hour.

Second step in the reaction (S) can carry out in the presence of alkali and solvent usually.

Alkali can suitably be selected from following one or more: for example organolithium compound, for example lithium methide and n-Butyl Lithium; And Grignard reagent, for example isopropylmagnesium chloride.The consumption of alkali can be the 1-2 mole, and preferred 1-1.5 mole is by every mole of formula (XVII-1), formula (XVII-2), formula (XVIII-1) or formula (XVIII-2) compound.

The consumption of used formula (XIX) compound is the 1-3 mole in second step of reaction (S), and preferred 1-1.5 mole is by every mole of formula (XVII-1), formula (XVII-2), formula (XVIII-1) or formula (XVIII-2) compound.

If necessary, second step in the reaction (S) can carry out in the presence of rare gas element.Rare gas element can suitably be selected from for example nitrogen and argon gas.

The temperature of reaction in reaction second in (S) step is normally-100 to 50 ℃, preferred-70 to 25 ℃.Normally 1-48 hour reaction times, preferred 1-20 hour.

Reaction (T)

In reaction (T), R ¹, R ², Z, X ^a, X ^a', X ^b, X ^c, X ^d, X ^e, V and j as defined above.

The first step in the reaction (T) can be carried out in the presence of alkali and solvent usually.

Alkali can suitably be selected from following one or more: for example organolithium compound, for example lithium methide and n-Butyl Lithium; And Grignard reagent, for example isopropylmagnesium chloride.

The consumption of alkali can be the 1-2 mole, and preferred 1-1.5 mole is by every mole of formula (XVII-1), formula (XVII-2), formula (XVIII-1) or formula (XVIII-2) compound.

The consumption of used formula (XX) compound is the 1-3 mole in the first step of reaction (T), and preferred 1-1.5 mole is by every mole of formula (XVII-1), formula (XVII-2), formula (XVIII-1) or formula (XVIII-2) compound.

If necessary, the first step of reaction (T) can be carried out in the presence of rare gas element.Rare gas element can suitably be selected from for example nitrogen and argon gas.

The temperature of reaction of the first step is normally-100 to 50 ℃ in the reaction (T), preferred-70 to 25 ℃.Normally 1-48 hour reaction times, preferred 1-20 hour.

Second step in the reaction (T) can carry out in the presence of oxygenant and solvent usually.

Oxygenant can suitably be selected from following one or more: for example pyridinium chlorochromate and Manganse Dioxide.The consumption of oxygenant is the 1-10 mole, and preferred 1-3 mole is by every mole of formula (XXI-1) or formula (XXI-2) compound.

Solvent can be any solvent, as long as it is the solvent to reactionlessness.For example, solvent can be suitably to be selected from following one or more: aromatic hydrocarbons, for example benzene,toluene,xylene or chlorobenzene; Aliphatic hydrocrbon, for example tetracol phenixin, methyl chloride, chloroform, methylene dichloride, ethylene dichloride, trichloroethane, hexane or hexanaphthene.

Second temperature of reaction that goes on foot is normally 0-150 ℃ in the reaction (T), preferred 20-100 ℃.Normally 0.5-24 hour reaction times, preferred 1-12 hour.

Reaction (U)

In reaction (U), A, B, R ¹, R ²With Z as defined above.

Reaction (U) can be carried out according to above-mentioned reaction (A).

Reaction (V)

In reaction (V), A, B, R ¹, R ², U and Z as defined above.In addition, the thiocarbonyl agent can for example be Lawesson reagent or thiophosphoric anhydride.Reaction (V) comprises five elementary reactions (1) shown in the above-mentioned reaction scheme to (5), and the reaction conditions of each reaction will be discussed in more detail below.

Reaction (1) can be carried out in the presence of solvent usually.Solvent can be any solvent to reactionlessness, and solvent can be suitably to be selected from following one or more: aromatic hydrocarbons, for example benzene, toluene and dimethylbenzene; Aliphatic hydrocrbon, for example pentane, hexane, heptane, sherwood oil, volatile oil and sherwood oil; Ether, for example ether, dipropyl ether, dibutyl ether, tetrahydrofuran (THF) He diox; And dithiocarbonic anhydride.

The temperature of reaction of reaction (1) is normally-20 to 150 ℃, preferred 0-110 ℃.Normally 0.1-48 hour reaction times.

In reaction (1), the consumption of thiocarbonyl agent is the 0.4-2 mole, by every mole of formula (XII) compound.

Reaction (2) can be carried out according to above-mentioned reaction (R).

Reaction (3) can be carried out according to above-mentioned reaction (P).

Reaction (4) can be carried out according to above-mentioned reaction (N).

Reaction (5) can be carried out according to above-mentioned reaction (A).

Reaction (W)

In reaction (W), A, B, R ¹, R ²With Z as defined above.

Reaction (W) can be carried out according to above-mentioned reaction (A).

In addition, according to circumstances need, the amide derivatives of formula (I) or its salt can be with reference to disclosed method preparations among WO2001/60783 or the WO2003/27059.

The amide derivatives or its salt that contain formula (I) can be controlled harmful fungoid with low dosage as the fungicidal composition (hereinafter referred is a composition of the present invention) of activeconstituents, therefore can for example be used as agricultural or horticultural bactericidal composition.

Embodiment

The preferred embodiment of the present composition is described below.

Composition of the present invention is particularly useful as agricultural or gardens fungicidal composition as the fungicidal composition that can control harmful fungoid with low dosage.When as agricultural or horticultural bactericidal composition, composition of the present invention can be controlled harmful fungoid, for example phycomycete (Oomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes), imperfect fungi (Deuteromycetes) can be controlled the harmful fungoid that belongs to ascomycetes for example or basidiomycetes especially effectively.

It below is the object lesson of above-mentioned harmful fungoid.

Phycomycete can be a phytophthora for example, for example potato or tomato late blight bacterium (Phytophthora infestants), or tomato haiiro-eki-byo germ (pumpkin parasitica); Downy mildew Pseudomonas, for example bacterium of downy mildew of cucumber (Pseudoperonospora cubensis); Single shaft downy mildew class (Plasmopara), for example downy mildew of garpe bacterium (Plasmopara viticola); And rotten mold genus, for example rice seedlings yellow blight bacterium (Phthium graminicola), or wheat yellow blight bacterium (Pythium iwayamai).

Ascomycetes can be for example Erysiphe, for example wheat powdery mildew (Erysiphegraminis); Single softgel shell belongs to for example powdery mildew of cucumber bacterium (Sphaerotheca fuliginea), or powdery mildew of strawberry bacterium (Sphaerotheca humuli); Uncinula, for example uncinula necator bacterium (Uncinula necator); Podosphaera, for example apple mildew bacterium (Podosphaera leucotricha); Mycosphaerella, pea Mycosphaerellablight germ (Mycosphaerella pinodes) for example, apple stain germ (Mycosphaerella pomi), sigatoka bacterium (Mycosphaerella musicola), persimmon roundleaf pinta bacterium (Mycosphaerella nawae), or strawberry leaf spot fungi (Mycosphaerella fragariae); Venturia, for example apple black star bacteria (Venturiainaequalis), or peach black star germ (Venturia nashicola); The nuclear cavity Pseudomonas, for example barley vermiculated mottle germ (Pyrenophora teres), or stripe disease of barley bacterium (Pyrenophoragraminea); Sclerotinia, for example various sclerotium germs (SclerotiniaSclerotiorum) are kidney bean stem rot germ for example, cucumber sclerotiorum, cottony rot of cabbage bacterium, Chinese cabbage sclerotium germ, capsicum sclerotium germ, pimento sclerotium germ, or onion water soaking mode Bacteria erwinia, wheat snow big grain sclerotinia rot bacterium (Sclerotinia borealis), tomato sclerotium oryzicola bacterium (Sclerotinia minor), or clover sclerotium and rhizome rotten pathogenic bacteria (Sclerotiniatrifoliorum); Genus Botryolinia, for example peanut sclerotium oryzicola bacterium (Botryolinia arachidis); Cochliobolus belongs to, for example paddy rice brown patch germ (Cochliobolus miyabeanus); Little pair of cell Pseudomonas, for example cucumber didymella bryoniae (Didymella bryoniae); Gibberella, for example wheat sickle spore wilt (Gibberellazeae); Elsinoe, for example bitter rot or anthracnose of grape germ (Elsinoe ampelina), or citrus scab bacterium (Elsinoe fawcettii); Between base shell bacterium belong to for example oranges and tangerines stain germ (Diaporthe citri), or grape swelling arm germ (Diaporthe sp.); Chain sclerotinia sclerotiorum belongs to, for example rotten germ (Monilinia mali) of apple flower, or Monilinia fructicola (Monilinia fructicola); Belong to small cluster shell, for example grape anthracnose (Glomerella cingulata).

Basidiomycetes can be that for example silk nuclear belongs to, for example Rhizoctonia solani Kuhn (Rhizoctoniasolani); Ustilago, for example loose smut of wheat germ (Ustilago nuda); Puccinia, oat crown rot bacterium (Puccinia coronata) for example, wheat leaf rust bacterium (Puccinia recondita), or puccinia striiformis (Puccinia striiformis); Belong to nuclear line bacteria, for example wheat or barley are avenged rotten sclerotium oryzicola bacterium (Typhula incarnata, Typhula ishikariensisis).

Imperfect fungi can be a Septoria for example, wheat glume blight bacterium (Septorianodorum) for example, speckled leaf blotch bacterium (Septoria tritici); Staphlosporonites, for example various ash arrhizus bacterias (Botrytis cinerea), for example grape grey mould bacterium, the oranges and tangerines ash arrhizus bacteria, botrytis cinerea pers, botrytis cinerea, grey mould fruit rot of strawberry bacterium, the grey mould of egg plant bacterium, the kidney bean ash arrhizus bacteria, red bean ash arrhizus bacteria, grey mould rot of pea bacterium, the peanut ash arrhizus bacteria, the capsicum ash arrhizus bacteria, pimento ash arrhizus bacteria, romaine lettuce ash arrhizus bacteria, the onion ash arrhizus bacteria, the Herba Limonii Gmelinii ash arrhizus bacteria, carnation ash arrhizus bacteria, rose ash arrhizus bacteria, the wild pansy ash arrhizus bacteria, or the Sunflower Receptacle ash arrhizus bacteria, onion grey mold ear stem seasonal febrile diseases bacterium (Botrytis allii), or onion ash arrhizus bacteria (Botrytissquamosa, Botrytis byssoidea, Botrytis tulipae); Pyricularia Sacc., for example Pyricularia oryzae (Pyricularia oryzae); Cercospora, for example sugar beet leaf spot bacteria (Cercospora beticola), or persimmon brown patch germ (Cercospora kakivola); Colletotrichum, for example cucumber anthracnose (Colletotrichum orbiculare); Alternaria, apple black star bacteria (Alternaria alternata apple pathotype) for example, pears alternaria (Alternaria alternata Japanese pears pathotype), potato or tomato early blight bacterium (Alternaria solani), wild cabbage or Chinese cabbage black star germ (Alternariabrassicae), wild cabbage leaf spoting bacteria (Alternaria brassicola), onion or shallot black star germ (Alternaria porri); Genus Pseudocercosporella, for example rhizoctonia cerealis (Pseudocercosporella herpotrichoides); False odd amount in addition to the round number Pseudomonas, for example grape leaf spot fungi (Pseudocercospora vitis); Rhynchosporium spp, for example barley scold germ (Rhynchosporium secalis); Cladosporium, for example peach gibberellic hypha (Cladosporium carpophilum); Phomopsis, for example brown line germ of peach (Phomopsis sp.); Coil long spore and belong to, for example anthracnose of kaki bacterium (Gloeosporium kaki); Fulvia fulva belongs to, for example leaf muld of tomato bacterium (Fulvia fulva); With the mould genus of excellent spore, cucumber brown mould pinta bacterium (Corynespora cassiicola) for example.

Composition of the present invention can be controlled above-mentioned various harmful fungoid, and and then can control property or the property cured ground control various diseases.Particularly, the present composition can effectively be controlled at problematic various diseases, for example samping off of the seasonal febrile diseases of paddy rice, brown spot, banded sclerotial blight or paddy rice (Oryza sativa etc.) in agricultural and the gardening field; Powdery Mildew, head blight, leaf rust, stripe rust, reticulate pattern pinta, stripe disease, snow mold, snow blight, smut, banded sclerotial blight, Scald, leaf spot or the glume blight of cereal (Hordeum vulgare, Tricumaestivum etc.); The diplostomiasis of oranges and tangerines or head blight (Citrus spp. etc.); Blossom rot, Powdery Mildew, diplostomiasis, black spot or the head blight (Malus pumila) of apple (Pyrus serotina, Pyrus ussuriensis, Pyrus communis); The head blight of pears or diplostomiasis; The brown heart of peach (Prunuspersica etc.), head blight or brown line disease; The anthrax of grape (Vitis vinifera spp. etc.), anthrax, leaf spot, branch abdominal distension (swelling arm) or Powdery Mildew; Anthrax, roundleaf pinta or the brown spot of Japanese persimmon (Diospyros kaki etc.); Anthrax, Powdery Mildew, climing rot, brown spot or the Powdery Mildew of cucurbit (Cucumis melo etc.); Early blight, the haiiro-eki-byo of tomato (Lycopersicon esculentum), leaf mold or late blight; Banana (Musa sapientum, etc.) leaf spot; The brown spot of beet (Beta vulgaris var.saccharifera, etc.); The climing rot of pea (Pisum sativum); The various alternarias of brassicaceous vegetable (Brassica sp., Raphanus sp., etc.); Late blight or the early blight of potato (Solanum tuberosum); Powdery Mildew or the leaf spot of strawberry (Fragaria etc.); And the grey mold or the disease that cause by the sclerotium of various crops, for example beans, vegetables, fruit or flowers.Wherein, can resist effectively especially by cucumber (Cucumissativus), kidney bean (Phaseolus vulgaris), red bean (Vigna angularis), soybean (Glycine max), pea, peanut (Arachis hypogaea), tomato, strawberry, eggplant (Solanum melongena), capsicum (Capsicum annuum), pimento (Capsicumannuum), romaine lettuce (Lactuca sativa), onion (Allium cepa), grape, oranges and tangerines, Herba Limonii Gmelinii (Limonium spp.), carnation (Dianthus spp.), rose (Rosaspp.), various grey mold or disease that the black spot of pea (Viola, etc.) or Sunflower Receptacle (Helianthus annuus) causes.

In addition, composition of the present invention also control by for example germ soil disease of Fusarium, pythium spp, Rhizoctonia, Verticillium and plasmodiophora brassicae platymiscium effectively by control property or treatment ground.

In addition, composition of the present invention also can be controlled the various germs that sterilant had resistance effectively, and sterilant is for example benzimidazoles, methoxy acrylate, two carbon imines, phenyl amide and ergosterol biosynthesis inhibitor.

In addition, composition of the present invention has the excellent permeation migration performance and when the applications of pesticide that will contain the present composition are in soil, can control the harmful fungoid on root and the leaf in the harmful fungoid in the control soil.

Composition of the present invention is generally prepared by the amide derivatives of formula (I) expression or its salt are mixed with various agricultural agents, and as the ingredients use of for example following form: the ingredients of pulvis, particle, water dispersible particle, wettable pulvis, water base suspending concentrate, oil base suspending concentrate, water-soluble granular, emulsifiable concentrate, the concentrated thing of solubility, thickener, aerosol or ultralow volume.But,, can be mixed with any type of ingredients commonly used in this area as long as be suitable for purpose of the present invention.These agricultural agents comprise solid carrier, for example diatomite, white lime, lime carbonate, talcum, white carbon black, kaolin, wilkinite, the mixture of wilkinite and silk Muscovitum, clay, yellow soda ash, sodium bicarbonate, saltcake, zeolite and starch; Solvent, for example water, toluene, dimethylbenzene, petroleum naphtha, diox, acetone, isophorone, methyl iso-butyl ketone (MIBK), chlorobenzene, hexanaphthene, dimethyl sulfoxide (DMSO), N, dinethylformamide, N,N-DIMETHYLACETAMIDE, N-N-methyl-2-2-pyrrolidone N-, and alcohol; Anion surfactant and spreading agent, the salt of lipid acid for example, benzoate, alkyl sulfo succinate, dialkyl sulfosuccinates, polycarboxylate, the salt of alkyl sulfuric ester, alkyl-sulphate, alkyl aryl sulfate, the alkyl diol ether sulfate, the salt of sulfuric acid alcohol ester, alkylsulfonate, alkylaryl sulphonate, arylsulphonate, Sulfite lignin, alkyl diphenyl base ether stilbene-4,4'-bis-(1-azo-3, 4-dihydroxy-benzene)-2,2'-disulfonate, poly styrene sulfonate, the salt of alkyl phosphate, alkylaryl phosphoric acid salt, the vinylbenzene aryl orthophosphate, the salt of Voranol EP 2001 sulfuric ester, the salt of polyoxyethylene alkylaryl ether sulfuric ester, Voranol EP 2001 phosphoric acid salt, the salt of polyoxyethylene alkylaryl ether phosphoric acid ester, and the salt of the condenses of naphthalenesulfonate and formalin formation; Nonionogenic tenside and distribution agent, fatty acid esters of sorbitan for example, glycerol fatty acid ester, the fatty acid polyglycol glycosides, fatty acid alcohol polyglycol ether, acetylenediol, acetylene alcohol, the oxyalkylene block polymer, Voranol EP 2001, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ethers, polyethylene glycol alkyl ether, polyoxyethylene glycol, polyoxyethylene fatty acid ester, Vykamol Sorbitol 8B, the polyoxyethylene glycerol fatty acid ester, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid ester; Vegetables oil and mineral oil, for example sweet oil, baobab oil, Viscotrol C, plam oil, Camellia oil, Oleum Cocois, sesame oil, Semen Maydis oil, Rice pollard oil, peanut oil, Oleum Gossypii semen, soya-bean oil, rapeseed oil, linseed oil, tung oil and whiteruss.Various components as auxiliary agent can be one or more that are suitable for, as long as can realize the object of the invention.In addition, also can use various additives commonly used, for example filler, thickening material, antisettling agent, frostproofer, dispersion stabilizer, phytotoxicity reduce agent and antimycotic agent.

By the amide derivatives of formula (I) expression or the weight ratio between its salt and the various agricultural agent normally 0.001: 99.999 to 95: 5, preferred 0.005: 99.995 to 90: 10.

In actual the using of this ingredients, can be used as it is, maybe can be diluted to predetermined concentration with thinner, thinner for example is a water, and according to circumstances needs, can be to wherein adding various distribution agent, for example tensio-active agent, vegetables oil or mineral oil.

Using of the present composition can not limit prevailingly because its can be according to weather condition, ingredients type, crop to be processed, use season, use the place, the type or the outburst degree of the type of harmful fungoid or germination state and disease change.But usually used activity component concentration is 0.1-10 under the situation that cauline leaf is handled, 000ppm, and preferred 1-2,000ppm, and its dosage makes the amide derivatives of formula (I) or its salt normally by the 0.1-50 of per hectare, 000g, preferred 1-30,000g.Under case of soil treatment, normally used dosage makes the amide derivatives of formula (I) or its salt normally by the 10-100 of per hectare, 000g, preferred 200-20,000g.

Containing the ingredients of the present composition or its diluted product can use by application process commonly used, for example distribute (distribution, sprinkling, spraying, atomizing, particle diffusion or use on the water surface), soil application (for example mix or irrigate) or surface applied (for example apply, powder is coated with or cover).In addition, also can use by so-called ultralow volume.In the method, ingredients can contain 100% activeconstituents.

Composition of the present invention can mix with other agrochemicals, fertilizer or phytotoxicity minimizing agent or can be used in combination with them, thereby can obtain synergy or activity sometimes.These other agrochemicals can for example be weedicide, sterilant, miticide, nematocides, soil insecticide, sterilant, antiviral agent, attractive substance, antibiotic, plant hormone and plant-growth regulator.Particularly, have and one or more other fungicide active ingredient compound or formula (I) amide derivatives that is used in combination or the fungicidal composition of its salt, can be improved to preferred direction using scope, time of application, fungicidal activity etc. by use.Here, formula (I) amide derivatives or its salt and other fungicide active ingredient compound can be prepared respectively so that they can mix use when using, and perhaps they can prepare application together.The present invention includes this blended fungicidal composition.

The mixture ratio of formula (I) amide derivatives or its salt and other fungicide active ingredient compound can not limit prevailingly, because it can change according to the type of weather condition, ingredients type, crop to be processed, time of application, the type of using place, harmful fungoid or germination state and disease or state etc., but this mixed weight is than usually in 1: 300 to 300: 1 scope, preferred 1: 100 to 100: 1.In addition, the dosage that is used to use can be so that the total amount of active compound be the 0.1-70 by per hectare, 000g, preferred 1-30,000g.The present invention includes by using this blended fungicidal composition and control the method for harmful fungoid.

Active compound component (the popular name of the sterilant in described other agrochemicals; Be included in use those or according to the test number of Japanese plant protection association) can for example be following:

The anilino-pyrimidine compound, mepanipyrim for example, phonetic mould amine or cyprodinil;

Pyridine amine compound, for example fluazinam;

Azole compounds, for example three is safe fragrant, than howing farming, Te Fuling, etaconazole, Wocosin 50TK, flat gram seat, fluzilazol, the gram that goes out falls cyproconazole, De Keli, own azoles alcohol, furconazole, the chlorine spirit of going out, metconazole, fluorine ring azoles, fluorine ether azoles, the fumarate of the imidazoles that exposes to the sun, Sipconazole, prothioconazoles, triazole ethanol, flutriafol, Difenoconazole, fluquinconazole, RH-7592, bromine gram seat, Da Keli, three match azoles are slaughtered heat or simeconazoles, pefurazoate, cycltebuconazole or imibenconazole;

Quinoxaline compounds, mite manganese for example goes out;

Dithio carbamate compounds, maneb for example, zineb, zinc manganese ethylenebisdithiocarbamate, polyurethane(s), Carbatene or zinc 1,2-propylene bisdithiocarbamate;

Organochlorine compound, phthalide for example, daconil or quintozene;

Imidazolium compounds, for example exempt to rely, thiophanate_methyl, Bei Fen replace or cyanogen frost azoles;

The malonamide nitrile compound, for example white urea cyanogen;

The phenyl amide compound, metaxanin for example, metaxanin M, the spirit of Evil frost, ofurace, Ben Dale originally reaches happy M, furalaxyl or cyprofuram;

Sulfenic acid compound, for example spirit increasingly;

Copper compound, for example copper hydroxide or rather fast;

Isoxazole compound is for example disliked mould spirit;

Organo phosphorous compounds, phosethyl Al for example, tolclofosmethyl, S-benzyl O, O-di-isopropyl thiophosphatephosphorothioate, O-ethyl S, S-phenylbenzene phosphorodithioate or ethyl hydrogen phosphonic acids aluminium;

N-halo alkylthio compound, Vancide 89 for example, Difolatan or Phaltan;

The dicarboxyl imide compound, procymidone for example, RP-26019 or Vinclozoline;

N-benzanilide compound, fultolanil for example, mebenil, Zoxamid or tiadinil

Aniline compound, for example boscalid amine;

Diethylenediamine compound, for example triforine;

Pyridine compounds is pyrifenox for example;

Carbinol compound, for example fenarimol or flutriafol;

Piperidine compounds, for example fenpropidin;

Morpholinium compound, for example Fen Pufu or tridemorph;

Organo-tin compound, for example fentin hydroxide or triphenyltin acetate;

Carbamide compound, for example pencycuron;

Styracin compound, for example dimethomorph or flumorph;

Phenylcarbamate compound, for example ten thousand mould spirits;

Cyanopyrrole compound, for example fludioxonil or fenpiclonil;

The methoxy acrylate compound, for example peace is gone out and is reached, kresoxim-methyl, the benzene pyrrole bacterium that falls, oxime bacterium ester, ZEN 90160, Oryzastrobin, ether bacterium amine, fluorine ring azoles ten, fluoxastrobin or Fluacrypyrim;

Oxazoline ketone compound, for example Famoxate;

Thiazole carboxamide compound, for example Guardian;

Silyl amide compound, for example silicon metsulfovax;

Amino acid amide carbamate compounds, for example iprovalicarb or benzene metsulfovax;

Imidazolidinone compound, for example fenamidone;

Hydroxyanilines compound, for example fenhexamid;

Benzenesulfonamide compounds, for example flusulfamide;

Oxime ether compound, for example cyflufenamid;

Phenoxy group amide compound, for example zarilamid;

Antibiotic, for example polyoxin;

Guanidine compound, for example iminoctadine;

Other compound, isoprothiolane for example, pyroquilon, diclomezin, benzene oxygen quinoline, hydrochloric acid hundred dimension prestige, sporidesmin Trichloronitrobenzene, dazomet, become hundred mu, Nicobifen, metrafenone MTF-753 (Pentiopyrad), UBF-307, two chlorine zarilamids, the third oxygen quinoline, NC-224 (Amibromdole, Amisulbrom), KIF-7767 (KUF-1204, PyribencarbMethyl, Mepyricarb) or Syngenta 446510 (Mandipropamid, Dipromandamid).

Active compound component (the popular name of sterilant, miticide, nematocides or soil insecticide in these other agrochemicals; Be included in those that use) can for example be:

The organic phosphoric acid salt compound, Profenofos for example, SD-1750, fenvalerate, fenitrothion 95, EPN, diazinon, chlorpyrifos_methyl, acephate, Toyodan, lythidathion, the second third phosphorus prestige, cadusafos, thiodemeton, Chlorpyrifos, demeton_S_methyl, Le Ge or acephatemet;

Carbamate compounds, sevin for example, Propoxur, aldicarb, carbofuran, the two prestige of sulphur, go out becomes oxamyl, benzene worm prestige, Aphox, fenobucarb, hundred one-tenth of carbosulfan or rosickyite grams more;

The Nelicetoxin derivative, cartap for example, thiocyclam or bensultap;

Organochlorine compound, for example kelthane or tetradifon;

Organometallic compound, for example fenbutatin oxide;

Pyrethroid compound, fenvalerate for example, permethrin, Cypermethrin, bromine cyanogen chrysanthemum, cyhalothrin, tefluthrin, ether chrysanthemum ester, Fenvalerate or bifenthrin;

The benzoyl carbamide compound, diflubenzuron for example, fluorine pyridine urea, benzoyl urea, stuck gram, the fragrant new or napropamide of chlorine;

The plain compound of juvenoid, methoprene for example, pyrrole propyl ether or fenoxycarb;

The Pyridadinone compound for example reaches mite ketone;

Pyrazole compound, azoles mite ester for example, fluorine worm nitrile, tebufenpyrad, ethiprole, azoles insect amide, Acetoprole, Pyrafluprole or Pyriprole;

Neonicotine, Provado for example, Ti304, pyridine worm miaow, thiophene worm quinoline, thiophene worm piperazine, clothianadin or MTI-446;

Hydrazine compound, worm hydrazides for example, methoxyfenozide or ring worm hydrazides;

Dinitro compound, organosulfur compound, carbamide compound, triaizine compounds or hydrazone compound;

Other compound, flonicamid for example, Buprofezin, hexythiazox, Amitraz, chlordimeform, silicon ether chrysanthemum ester, triaxamate, pyrrole aphid ketone, pyrimidifen, bromothalonil, indenes worm prestige, the mite quinone that goes out, second mite azoles, cyromazine, 1,3-dichloropropylene, butyl ether urea, Benclothiaz, Flufenerim, pyridalyl, spiral shell mite ester, bifenthrin, season ketone first mite ester, Spirotetramat, propargite, four mite piperazines, Fluacrypyrim, Metaflumizone, Flubendiamide or Cyflumetofen.

In addition, microbial pesticide, BT reagent for example, insect pathogenic virus reagent, carnivorism bacterium or food nematode bacterium;

Antibiotic, Avrmectin for example, emamectin-benzoate, the close spit of fland of going out, pleocidin, ivermectin or Lepimectin;

Natural product, for example nimbin.

The preferred embodiments of the invention are as follows.But, it should be understood that the present invention is not subjected to the restriction of these specific embodiments.

(1) amide derivatives of above-mentioned formula (I) or its salt.

(2) amide derivatives of above-mentioned formula (I) or its salt, wherein A is the phenyl that does not replace or replaced by X, does not replace or by the naphthyl that X replaces, the heterocycle that does not replace or replaced by X, or the annelated heterocycles that does not replace or replaced by X; B is the heterocycle (not comprising pyridyl) that does not replace or replaced by Y, the annelated heterocycles that does not replace or replaced by Y, or the naphthyl that does not replace or replaced by Y; X is a halogen; (alkyl can be by halogen for alkyl; hydroxyl; alkoxyl group; halogenated alkoxy; the alkyl sulfenyl; alkyl sulphonyl; cycloalkyl; amino; alkyl monosubstituted amino; dialkyl amido; cyano group; alkoxy carbonyl or alkyl-carbonyl oxygen base replace); alkenyl; halogenated alkenyl; (alkynyl can be by halogen for alkynyl; hydroxyl; alkoxyl group; amino; hydroxycarbonyl group; alkoxy carbonyl or trialkylsilkl replace); hydroxyl; cyano group oxygen base; (alkoxyl group can be by halogen for alkoxyl group; alkoxyl group; halogenated alkoxy; the alkyl sulfenyl; cycloalkyl; alkyl monosubstituted amino; dialkyl amido; cyano group or heterocyclic substituted); alkenyl oxy; halogenated alkenyl oxy; the alkynyloxy base; halo alkynyloxy base; (the alkyl sulfenyl can be by halogen for the alkyl sulfenyl; cycloalkyl or cyano group replace); alkenyl thio; the halogenated alkenyl sulfenyl; the alkynyl sulfenyl; halo alkynyl sulfenyl; the alkyl sulfinyl; the haloalkyl sulfinyl; alkyl sulphonyl; halogenated alkyl sulfonyl; the cycloalkyl that does not replace or replaced by halogen; the cycloalkyl oxy that does not replace or replaced by halogen; the cycloalkyl sulfenyl that does not replace or replaced by halogen; cyano group; nitro; formyl radical; (phenyl can be by halogen for phenyl; alkyl; haloalkyl or alkoxyl group replace); the phenoxy group that does not replace or replaced by alkyl; the phenyl sulfenyl that does not replace or replaced by alkyl; the phenylalkyl that does not replace or replaced by alkyl; the phenyl alkenyl that does not replace or replaced by alkyl; the phenyl alkynyl that does not replace or replaced by alkyl; the phenylalkyl oxygen base that does not replace or replaced by alkyl; the phenyl alkenyl oxy that does not replace or replaced by alkyl; do not replace or by the phenyl alkynyloxy base that alkyl replaces the phenyl amino that does not replace or replaced by alkyl ,-OR ⁴,-SR ⁵,-NR ⁶R ⁷,-CO ₂R ⁸,-C (=O) NR ⁸R ⁹,-SO ₂NR ⁸R ⁹,-CH=NR ¹⁰, or heterocycle (heterocycle can be replaced by halogen, alkyl or alkyl-carbonyl); Y is a halogen, alkyl (alkyl can be replaced by halogen, alkoxyl group, halogenated alkoxy, amino, alkyl monosubstituted amino or dialkyl amido), alkenyl; alkynyl, hydroxyl, alkoxyl group; halogenated alkoxy, alkyl sulfenyl, haloalkyl sulfenyl; the alkyl sulfinyl, haloalkyl sulfinyl, alkyl sulphonyl; halogenated alkyl sulfonyl, cycloalkyl, cyano group; nitro, formyl radical ,-OR ⁴,-NR ⁶R ⁷,-CO ₂R ⁸,-C (=O) NR ⁸R ⁹,-SO ₂NR ⁸R ⁹, or-CH=NR ¹⁰R ¹And R ²Be hydrogen independently of one another, alkyl, haloalkyl, alkoxyalkyl, alkenyl, alkynyl, or cycloalkyl, or R ¹And R ²Can form 3-6 unit saturated carbon ring together; R ³Be hydrogen, alkyl (alkyl can be replaced by halogen, alkoxyl group, halogenated alkoxy, alkyl sulfenyl, amino, alkyl monosubstituted amino, dialkyl amido or cyano group), alkenyl, alkynyl; hydroxyl, alkoxyl group, halogenated alkoxy, cycloalkyl; cycloalkyl oxy, cyano group, formyl radical ,-C (=W ³) R ¹¹,-C (=W ³) OR ¹², or-S (O) mR ¹²

(3) described amide derivatives or its salt, wherein A is the phenyl that does not replace or replaced by X, does not replace or by the naphthyl that X replaces, the heterocycle that does not replace or replaced by X, or the annelated heterocycles that does not replace or replaced by X; B is 5 yuan of heterocycles that do not replace or replaced by Y, pyrazinyl, or the annelated heterocycles that does not replace or replaced by Y; X is a halogen, alkyl, haloalkyl, alkoxyalkyl, dialkyl aminoalkyl, alkynyl, trialkylsilkl alkynyl, hydroxyl, alkoxyl group, halogenated alkoxy, the alkoxyl group alkoxyl group, cycloalkyl, nitro, phenyl, phenyl alkynyl, the pyridyl oxygen base that does not replace or replaced by haloalkyl, the alkyl-carbonyl oxygen base, alkyl sulphonyl oxygen base, or heterocycle (heterocycle can be replaced by halogen, alkyl or alkyl-carbonyl); Y is a halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, cycloalkyl, or formyl radical; R ¹And R ²Be hydrogen or alkyl independently of one another; R ³Be hydrogen, alkyl, alkyl-carbonyl, or alkoxy carbonyl; Each W ¹And W ²Be oxygen or sulphur independently of one another.

(4) according to amide derivatives or its salt, the wherein W of above-mentioned (3) ¹And W ²Each is oxygen naturally.

(5) according to amide derivatives or its salt of above-mentioned (3), wherein B is the annelated heterocycles that does not replace or replaced by Y.

(6) according to amide derivatives or its salt of above-mentioned (5), wherein said annelated heterocycles is a benzofuryl, dihydro benzo furyl, benzodioxan base or quinolyl.

(7) according to amide derivatives or its salt of above-mentioned (3), wherein B is 5 yuan of heterocycles that do not replace or replaced by Y; X is a halogen, alkyl, haloalkyl, alkynyl, hydroxyl, alkoxyl group, halogenated alkoxy, alkoxyl group alkoxyl group, cycloalkyl, nitro, phenylalkyl, the pyridyl oxygen base that does not replace or replaced by haloalkyl, alkyl-carbonyl oxygen base, or heterocycle (heterocycle can be replaced by halogen, alkyl or alkyl-carbonyl); Y is a halogen, alkyl, haloalkyl, or alkoxyl group; R ³Be hydrogen, alkyl-carbonyl, or alkoxy carbonyl; W ¹And W ²Each is oxygen naturally.

(8) according to amide derivatives or its salt of above-mentioned (3) or (7), wherein B is the furyl that does not replace or replaced by Y, the thienyl that does not replace or replaced by Y, do not replace or by the pyrryl that Y replaces, replace or replaced the De oxazolyl, replace or replaced the De isoxazolyl by Y by Y, the thiazolyl that does not replace or replaced by Y, do not replace or by the isothiazolyl that Y replaces the pyrazolyl that does not replace or replaced by Y, or the thiadiazolyl group that does not replace or replaced by Y.

(9) according to amide derivatives or its salt of above-mentioned (8), wherein B is the furyl that does not replace or replaced by Y, the thienyl that does not replace or replaced by Y, do not replace or by the pyrryl that Y replaces, replace or replaced the De oxazolyl, replace or replaced the De isoxazolyl by Y by Y, the thiazolyl that does not replace or replaced by Y, do not replace or by the isothiazolyl that Y replaces the pyrazolyl that does not replace or replaced by Y, or the thiadiazolyl group that does not replace or replaced by Y.

(10) according to amide derivatives or its salt of above-mentioned (9), the furyl that replaced by Y of B wherein.

(11) according to amide derivatives or its salt of above-mentioned (9), the thienyl that replaced by Y of B wherein.

(12) according to amide derivatives or its salt of above-mentioned (9), the pyrazolyl that replaced by Y of B wherein.

(13) amide derivatives or its salt of above-mentioned formula (I-α).

(14) amide derivatives or its salt of above-mentioned formula (I-α), wherein B is 5 yuan of heterocycles that do not replace or replaced by Y, pyrazinyl, or the annelated heterocycles that does not replace or replaced by Y; X ^αThe is fluorine, chlorine, iodine, alkyl, haloalkyl, alkoxyalkyl, dialkyl aminoalkyl, alkynyl, the trialkylsilkl alkynyl, hydroxyl, alkoxyl group, halogenated alkoxy, the alkoxyl group alkoxyl group, cycloalkyl, nitro, phenyl, phenyl alkynyl, the pyridyl oxygen base that does not replace or replaced by haloalkyl, the alkyl-carbonyl oxygen base, alkyl sulphonyl oxygen base, or heterocycle (heterocycle can be replaced by halogen, alkyl or alkyl-carbonyl); Y is a halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, cycloalkyl, or formyl radical; R ¹And R ²Be hydrogen or alkyl independently of one another; R ³Be hydrogen, alkyl, alkyl-carbonyl, or alkoxy carbonyl; W ¹And W ²Be oxygen or sulphur independently of one another.

(15) according to amide derivatives or its salt, the wherein W of above-mentioned (14) ¹And W ²Each is oxygen naturally.

(16) according to amide derivatives or its salt of above-mentioned (14), wherein B is the annelated heterocycles that does not replace or replaced by Y.

(17) according to amide derivatives or its salt of above-mentioned (16), wherein said annelated heterocycles is a benzofuryl, dihydro benzo furyl, benzodioxan base or quinolyl.

(18) according to amide derivatives or its salt of above-mentioned (14), wherein B is 5 yuan of heterocycles that do not replace or replaced by Y; X ^αBe fluorine, chlorine, iodine, alkyl, haloalkyl, alkynyl, hydroxyl, alkoxyl group, halogenated alkoxy, the alkoxyl group alkoxyl group, cycloalkyl, nitro, the phenyl alkynyl, the pyridyl oxygen base that does not replace or replaced by haloalkyl, alkyl-carbonyl oxygen base, or heterocycle (heterocycle can be replaced by halogen, alkyl or alkyl-carbonyl); Y is a halogen, alkyl, haloalkyl, or alkoxyl group; R ³Be hydrogen, alkyl-carbonyl, or alkoxy carbonyl; W ¹And W ²Each is oxygen naturally.

(19) according to amide derivatives or its salt of above-mentioned (14) or (18), wherein B is the furyl that does not replace or replaced by Y, the thienyl that does not replace or replaced by Y, do not replace or by the pyrryl that Y replaces, replace or replaced the De oxazolyl, replace or replaced the De isoxazolyl by Y by Y, the thiazolyl that does not replace or replaced by Y, do not replace or by the isothiazolyl that Y replaces the pyrazolyl that does not replace or replaced by Y, or the thiadiazolyl group that does not replace or replaced by Y.

(20) according to amide derivatives or its salt of above-mentioned (19), wherein B is the furyl that does not replace or replaced by Y, the thienyl that does not replace or replaced by Y, do not replace or by the pyrryl that Y replaces, replace or replaced the De oxazolyl, replace or replaced the De isoxazolyl by Y by Y, the thiazolyl that does not replace or replaced by Y, do not replace or by the isothiazolyl that Y replaces the pyrazolyl that does not replace or replaced by Y, or the thiadiazolyl group that does not replace or replaced by Y.

(21) according to amide derivatives or its salt of above-mentioned (20), the furyl that replaced by Y of B wherein.

(22) according to amide derivatives or its salt of above-mentioned (20), wherein B is by Y substituted thiophene base.

(23) according to amide derivatives or its salt of above-mentioned (20), the pyrazolyl that replaced by Y of B wherein.

(24) according to amide derivatives or its salt of above-mentioned (3) or (14), wherein A does not replace or by the phenyl that X replaces, and does not replace or by the naphthyl that X replaces, the benzo dioxolanyl that does not replace or replaced by X, or the benzodioxan base that does not replace or replaced by X; B is the furyl that does not replace or replaced by Y, the thienyl that does not replace or replaced by Y, or the pyrazolyl that does not replace or replaced by Y; X is a halogen, alkyl, haloalkyl, alkoxyl group, or halogenated alkoxy; Y is a halogen, alkyl, haloalkyl, alkoxyl group, or haloalkyl; R ³Be hydrogen; W ¹And W ²Each is oxygen naturally.

(25) according to amide derivatives or its salt of above-mentioned (24), the furyl that replaced by Y of B wherein, the thienyl that is replaced by Y, or the pyrazolyl that is replaced by Y.

(26) according to amide derivatives or its salt of above-mentioned (24), the wherein furyl that replaced by Y of B, the thienyl that is replaced by Y, the pyrazolyl that replaced by Y; Y is halogen, alkyl or haloalkyl.

(27) according to amide derivatives or its salt of above-mentioned (24), the phenyl that replaced by X of A wherein, or the benzo dioxolanyl that is replaced by X; The furyl that B is replaced by Y, the thienyl that is replaced by Y, or the pyrazolyl that is replaced by Y.

(28) according to amide derivatives or its salt of above-mentioned (24), the wherein phenyl that replaced by X of A or the benzo dioxolanyl that is replaced by X; The furyl that B is replaced by Y, the thienyl that is replaced by Y, or the pyrazolyl that is replaced by Y; X is halogen, alkyl or alkoxyl group; Y is halogen, alkyl or haloalkyl.

(29) according to amide derivatives or its salt of above-mentioned (24), the phenyl that replaced by X of A wherein, or the benzo dioxolanyl that is replaced by X; The furyl that B is replaced by Y, the thienyl that is replaced by Y, or the pyrazolyl that is replaced by Y; R ¹And R ²Each is alkyl naturally; X is halogen, alkyl or alkoxyl group; Y is halogen, alkyl or haloalkyl.

(30) according to each amide derivatives or its salt in above-mentioned (24)-(29), the furyl that replaced by Y of B wherein.

(31) according to each amide derivatives or its salt in above-mentioned (24)-(29), the thienyl that replaced by Y of B wherein.

(32) according to each amide derivatives or its salt in above-mentioned (24)-(29), the pyrazolyl that replaced by Y of B wherein.

(33) a kind of fungicidal composition, its contain in good grounds above-mentioned (1)-(32) each amide derivatives or its salt as activeconstituents.

(34) a kind of blended fungicidal composition, its contain in good grounds above-mentioned (1)-(32) each amide derivatives or its salt and other fungicide active ingredient compound as activeconstituents.

(35) according to the blended fungicidal composition of above-mentioned (34), wherein said other fungicide active ingredient compound is selected from following at least a: anilino-pyrimidine compound, pyridine amine compound, azole compounds, quinoxaline compounds, dithio carbamate compounds, organochlorine compound, imidazolium compounds, malonamide nitrile compound, the phenyl amide compound, sulfenic acid compound, copper compound; isoxazole compound, organo phosphorous compounds, N-halo alkylthio compound, the dicarboxyl imide compound, N-benzanilide compound, aniline compound, diethylenediamine compound, pyridine compounds, carbinol compound, piperidine compounds, morpholinium compound, organo-tin compound, carbamide compound, styracin compound, phenylcarbamate compound, the cyanopyrrole compound, methoxy acrylate compound ， oxazoline ketone compound, thiazole carboxamide compound, the silyl amide compound, the amino acid amide carbamate compounds, imidazolinium compounds, hydroxyanilines compound, benzenesulfonamide compounds, the oxime ether compound, phenoxy group amide compound, antibiotic, guanidine compound, isoprothiolane, pyroquilon, diclomezin, benzene oxygen quinoline, hydrochloric acid hundred dimension prestige, volution bacterium amine, trichloronitromethane, dazomet, become hundred mu, Nicobifen, metrafenone, MTF-753, UBF-307, two chlorine zarilamids, the third oxygen quinoline, NC-224, KIF-7767 and Syngenta 446510.

(36) according to the blended fungicidal composition of above-mentioned (35), wherein said other fungicide active ingredient compound be selected from following at least a: the pyridine amine compound, azole compounds, dithio carbamate compounds, organochlorine compound, imidazolium compounds, copper compound, the dicarboxyl imide compound, aniline compound, diethylenediamine compound, pyridine compounds, carbinol compound, phenylcarbamate compound, cyanopyrrole compound, the methoxy acrylate compound, the hydroxyanilines compound, MTF-753, and KIF-7767.

(37) according to the blended fungicidal composition of above-mentioned (36), wherein said other fungicide active ingredient compound be selected from following at least a: fluazinam, three is safe fragrant, than howing farming, Te Fuling, etaconazole, Wocosin 50TK, flat gram seat, fluzilazol, the gram that goes out falls cyproconazole, tebuconazole, own azoles alcohol, furconazole, the chlorine spirit of going out, metconazole, fluorine ring azoles, fluorine ether azoles, the fumarate of the imidazoles that exposes to the sun, Sipconazole, prothioconazoles, triazole ethanol, flutriafol, Difenoconazole, fluquinconazole, RH-7592, bromine gram seat, Da Keli, three match azoles are slaughtered heat, simeconazoles, pefurazoate, cycltebuconazole, imibenconazole, maneb, zineb, zinc manganese ethylenebisdithiocarbamate, polyurethane(s), Carbatene, zinc 1,2-propylene bisdithiocarbamate, phthalide, m-tetrachlorophthalodinitrile, quintozene, exempt to rely, thiophanate_methyl, Bei Fen replaces, cyanogen frost azoles, copper hydroxide, rather fast, procymidone, RP-26019, Vinclozoline, boscalid amine, ten thousand mould spirits, fludioxonil, fenpiclonil, peace is gone out and is reached, kresoxim-methyl, the benzene pyrrole bacterium that falls, oxime bacterium ester, ZEN 90160, Oryzastrobin, ether bacterium amine, fluorine ring azoles ten, fluoxastrobin, Fluacrypyrim, fenhexamid, polyoxin, iminoctadine, MTF-753, and KIF-7767.

(38) a kind of method of controlling harmful fungoid, comprise apply significant quantity according to each amide derivatives or its salt in above-mentioned (1)-(32).

(39) a kind of method of controlling plant disease, comprise apply significant quantity according to each amide derivatives or its salt in above-mentioned (1)-(32).

(40) method of a kind of cover crop, comprise apply significant quantity according to each amide derivatives or its salt in above-mentioned (1)-(32).

(41) a kind of method of improving crop yield, comprise apply significant quantity according to each amide derivatives or its salt in above-mentioned (1)-(32).

Now, reference example is further specified the present invention.But, it should be understood that the present invention is not subjected to the restriction of these embodiment.The amide derivatives of formula (I), (I-α) or the preparation embodiment of its salt at first will be described.

Preparation embodiment 1

Preparation N-[(3 ', 4 '-two chloro-1,1-dimethyl) phenacyl]-2-methyl-3-furoylamide (following compound N is o.1-57)

(1) will contain 3 of 10.0g, the 2-isobutyl ethyl bromide of 4-dichlorobenzoyl chloride, 9.31g and the mixture of 90ml anhydrous diethyl ether are added drop-wise in nitrogen atmosphere in the 3.12g zinc, react 15 hours under refluxing then.Reaction mixture uses C salt (celite) to filter then, and filtrate is used 20% sulfuric acid scrubbing, washes with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/19), obtain 8.7g buttery 2-(3 ', 4 '-dichloro-benzoyl base) isopropylformic acid ethyl ester.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.11(t，3H)，1.52(s，6H)，4.14(q，2H)，7.48(d，1H)，7.63(dd，1H)，7.96(d，1H)

(2) mixture that will contain 2-(3 ', 4 '-dichloro-benzoyl base) isopropylformic acid ethyl ester, 14.2ml sulfuric acid, 14.2ml water and the 40ml acetate of 8.7g reacted 15 hours under refluxing.Then reaction mixture is put into frozen water and used ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/19), obtain 6.47g buttery 3,4-dichloro isobutyl phenyl ketone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.21(d，6H)，3.46(m，1H)，7.55(d，1H)，7.79(dd，1H)，8.02(d，1H)

(3) the phenyl trimethylammonium tribromide ammonium adding with 9.32g contains 3 of 6.47g, in the mixture of 4-dichloro isobutyl phenyl ketone and 100ml tetrahydrofuran (THF), at room temperature reacts then 4 hours.Reaction mixture filters, and filtrate under reduced pressure concentrates, and obtains 6.39g buttery α-bromo-3,4-dichloro isobutyl phenyl ketone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

2.01(s，6H)，7.50(d，1H)，8.0(dd，1H)，8.20(d，1H)

(4) adding of 2.8g sodiumazide is contained 6.39g α-bromo-3, in the mixture of 4-dichloro isobutyl phenyl ketone and 60ml dimethyl sulfoxide (DMSO), then in 50 ℃ of reactions 1 hour.Then reaction mixture is put into water and used ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/9), obtain 6.34g buttery α-nitrine-3,4-dichloro isobutyl phenyl ketone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.60(s，6H)，7.53(d，1H)，7.97(dd，1H)，8.20(d，1H)

(5) triphenylphosphine of 7.74g is added contain 6.34g α-nitrine-3, in the mixture of 4-dichloro isobutyl phenyl ketone, 90ml tetrahydrofuran (THF) and 3.2ml water, then room temperature reaction 23 hours.Reaction mixture under reduced pressure concentrates.In resistates, add entry, add hydrochloric acid then, wash with ether then so that it is slightly acidic.The waterbearing stratum neutralizes with aqueous sodium hydroxide solution, and uses extracted with diethyl ether.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.In resistates, add ethyl acetate, and introducing hydrogen chloride gas with ice-cooled time.Formed solid by filtration is collected, and dry, obtains the alpha-amino group-3 of 5.92g, 4-dichloro isobutyl phenenyl keto hydrochloride.

(6) the triethylamine adding with 0.31g contains 0.3g alpha-amino group-3, in the mixture of 4-dichloro isobutyl phenenyl keto hydrochloride and 10ml tetrahydrofuran (THF), at room temperature stirs then 5 hours.This mixture under reduced pressure concentrates.In the mixture of 2-methyl-3-furancarboxylic acid that contains gained resistates, 0.195g and 20ml methylene dichloride, be added dropwise to the N that contains 0.29g with ice-cooled time, the mixture of N '-dicyclohexylcarbodiimide and 10ml methylene dichloride at room temperature reacted 15 hours then.Reaction mixture filters, and filtrate is diluted with methylene dichloride, and with the wet chemical washing, washes with water then.The organic layer anhydrous sodium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=1/9), the fusing point that obtains 0.08g is 175-178 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.71(s，6H)，2.43(s，3H)，6.28(s，1H)，6.44(d，1H)，7.26(d，1H)，7.44(d，1H)，7.84(dd，1H)，8.11(d，1H)

Preparation embodiment 2

Preparation N-[(3 '-difluoro-methoxy-1, the 1-dimethyl) phenacyl]-5-chloro-1,3-dimethyl-4-pyrazolecarboxamide (following compound N is o.1-72)

(1) will use the Grignard reagent of 0.75g magnesium, 4.46g 2-N-PROPYLE BROMIDE and the preparation of 24ml anhydrous diethyl ether to be added drop-wise in the mixture that contains 4.09g 3-difluoro-methoxy cyanobenzene and 20ml anhydrous diethyl ether.After finishing dropping, this mixture at room temperature reacted 27 hours.Reaction mixture is put into frozen water, and add 6N sulfuric acid, stirred then 0.5 hour so that this mixture is slightly acidic.This mixture extracted with diethyl ether washes with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/19), obtain the 3-difluoro-methoxy isobutyl phenyl ketone of 2.04g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.23(d，6H)，3.52(m，1H)，6.56(t，1H)，7.32(dd，1H)，7.48(t，1H)，7.70(s，1H)，7.80(d，1H)

(2) the phenyl trimethylammonium tribromide ammonium adding with 3.58g contains in the mixture of 2.04g 3-difluoro-methoxy isobutyl phenyl ketone and 30ml tetrahydrofuran (THF), at room temperature reacts then 2 hours.This reaction mixture filters, and filtrate under reduced pressure concentrates, and obtains buttery α-bromo-3-difluoro-methoxy isobutyl phenyl ketone of 2.79g.

(3) the sodiumazide adding with 1.24g contains in the mixture of 2.79g α-bromo-3-difluoro-methoxy isobutyl phenyl ketone and 35ml dimethyl sulfoxide (DMSO), then in 50 ℃ of reactions 1 hour.Reaction mixture is put into water, and use ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/9), obtain buttery α-nitrine-3-difluoro-methoxy isobutyl phenyl ketone of 2.21g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.61(s，6H)，6.56(t，1H)，7.34(dd，1H)，7.48(t，1H)，7.86(s，1H)，7.98(d，1H)

(4) mixture that will contain 2.18g α-nitrine-3-difluoro-methoxy isobutyl phenyl ketone, 35ml methyl alcohol and 0.109g 5% palladium on carbon at room temperature reacted 1.5 hours in nitrogen atmosphere.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates.In resistates, add ethyl acetate, and, under reduced pressure concentrate then, obtain alpha-amino group-3-difluoro-methoxy isobutyl phenenyl keto hydrochloride of 1.76g with the ice-cooled hydrogen chloride gas of introducing down.

(5) the triethylamine adding with 0.33g contains in the mixture of 0.3g alpha-amino group-3-difluoro-methoxy isobutyl phenenyl keto hydrochloride and 10ml tetrahydrofuran (THF), and containing 0.25g 5-chloro-1 to wherein being added dropwise to, the mixture of 3-dimethyl-4-pyrazoles carbonyl chlorine and 5ml tetrahydrofuran (THF) down with ice-cooled.After finishing dropping, this mixture at room temperature reacted 3 hours.With the reaction mixture ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=1/4), the fusing point that obtains 0.23g is 138-139 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.75(s，6H)，2.28(s，3H)，3.80(s，3H)，6.50(t，1H)，6.80(s，1H)，7.23(dd，1H)，7.38(t，1H)，7.84(s，1H)，7.86(d，1H)

Preparation embodiment 3

Preparation N-[2-(2 '-naphthyl carbonyl)-2-propyl group]-5-chloro-1,3-dimethyl-4-pyrazolecarboxamide (compound N is o.2-1)

(1) will use the Grignard reagent of 0.61g magnesium, 3.6g 2-N-PROPYLE BROMIDE and the preparation of 18ml anhydrous diethyl ether to be added drop-wise in the mixture that contains 3.0g 2-naphthyl cyanide and 20ml anhydrous diethyl ether.After finishing dropping, mixture was reacted 12 hours under refluxing.Reaction mixture is put into frozen water, and add 6N sulfuric acid, stirred then 0.5 hour so that this mixture is slightly acidic.This mixture ethyl acetate extraction washes with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/50), obtain the 2-naphthyl nezukone of 1.14g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.27(d，6H)，3.73(m，1H)，7.53-7.65(m，2H)，7.86-7.92(m，2H)，7.97(d，1H)，8.03(dd，1H)，8.48(d，1H)

(2) the phenyl trimethylammonium tribromide ammonium adding with 2.16g contains in the mixture of 1.14g 2-naphthyl nezukone and 25ml tetrahydrofuran (THF), and this mixture at room temperature reacted 3 hours then.This reaction mixture filters, and filtrate under reduced pressure concentrates, and obtains buttery α-bromine sec.-propyl 2-naphthyl ketone of 1.59g.

(3) the sodiumazide adding with 0.75g contains in the mixture of 1.59g α-bromine sec.-propyl 2-naphthyl ketone and 40ml dimethyl sulfoxide (DMSO), and this mixture was in 50 ℃ of reactions 1.5 hours then.Reaction mixture is put into water, and use ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/9), obtain buttery α-nitrine sec.-propyl 2-naphthyl ketone of 1.19g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.68(s，1H)，7.54-7.66(m，2H)，7.86-7.90(m，2H)，7.98(d，1H)，8.10(dd，1H)，8.74(d，1H)

(4) mixture that will contain 0.3g α-nitrine sec.-propyl 2-naphthyl ketone, 10ml methyl alcohol and 15mg 5% palladium on carbon at room temperature reacted 1 hour in nitrogen atmosphere.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates.Obtain the buttery alpha-amino group sec.-propyl 2-naphthyl ketone of 0.26g.

(5) the triethylamine adding with 0.19g contains in the mixture of 0.26g alpha-amino group sec.-propyl 2-naphthyl ketone and 10ml tetrahydrofuran (THF), and containing 0.24g 5-chloro-1 to wherein being added dropwise to, the mixture of 3-dimethyl-4-pyrazoles carbonyl chlorine and 5ml tetrahydrofuran (THF) down with ice-cooled.After finishing dropping, this mixture at room temperature reacted 15 hours.With the reaction mixture ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=2/3), the fusing point that obtains 0.15g is 145-147 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.87(s，6H)，2.28(s，3H)，3.79(s，3H)，7.05(s，1H)，7.48-7.58(m，2H)，7.80-7.90(m，3H)，8.05(dd，1H)，8.56(d，1H)

Preparation embodiment 4

Preparation N-[2-[(2 ', 2 ', 3 ', 3 '-tetrafluoro-1 ', the carbonyl of 4 '-benzodioxan-6 '-yl)] sec.-propyl]-3-methyl-2-thenoyl amine (following compound N is o.4-10)

(1) n-Butyl Lithium (1.57M hexane solution) of 7.3ml is added drop-wise in nitrogen atmosphere in-50 ℃ contains 3.0g 6-bromo-2,2,3,3-tetrafluoro-1 in the mixture of 4-benzodioxan and 38ml ether, stirred 30 minutes under uniform temp then.Under temperature at the most-70 ℃, drip the isobutyric aldehyde of 0.83g then, and with mixture heating up to room temperature, reacted 15 hours.Reaction mixture is put into water, be adjusted to slightly acidic, and use extracted with diethyl ether with hydrochloric acid.Organic layer washes with water, uses dried over mgso, under reduced pressure concentrates then.Resistates by silica gel column chromatography purify (developping agent: ethyl acetate/normal hexane=1/9), obtain 1.8g buttery 1-(2 ', 2 ', 3 ', 3 '-tetrafluoro-1 ', 4 '-benzodioxan-6 '-yl)-2-methylpropanol.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

0.83(d，3H)，0.96(d，3H)，1.92(m，1H)，4.40(d，1H)，6.90(d，1H)，7.10(s，2H)，7.14(s，1H)

(2) will contain 1.8g 1-(2 ', 2 ', 3 ', 3 '-tetrafluoro-1 ', the mixture of 4 '-benzodioxan-6 '-yl)-2-methylpropanol and 7ml methylene dichloride adds and contains in the mixture of 2.08g pyridinium chlorochromate, 1.05 sodium acetates and 20ml methylene dichloride, then room temperature reaction 2 hours.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/19), obtain the buttery 2,2,3 of 1.40g, 3-tetrafluoro-1,4-benzodioxan-6-base nezukone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.23(d，6H)，3.48(m，1H)，7.24(d，1H)，7.78(d，1H)，7.81(dd，1H)

(3) the phenyl trimethylammonium tribromide ammonium adding with 1.89g contains 1.40g 2,2,3, and 3-tetrafluoro-1 in the mixture of 4-benzodioxan-6-base nezukone and 19.7ml tetrahydrofuran (THF), at room temperature reacted 2 hours then.This reaction mixture filters, and filtrate under reduced pressure concentrates, and obtains buttery α-bromine sec.-propyl 2,2,3 of 1.78g, 3-tetrafluoro-1,4-benzodioxan-6-base ketone.

(4) the sodiumazide adding with 0.65g contains 1.78g α-bromine sec.-propyl 2,2,3, and 3-tetrafluoro-1 is in the mixture of 4-benzodioxan-6-base ketone and 10ml dimethyl sulfoxide (DMSO), then in 50 ℃ of reactions 2 hours.Reaction mixture is put into water, and use extracted with diethyl ether, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/19), obtain buttery α-nitrine sec.-propyl 2,2,3 of 1.5g, 3-tetrafluoro-1,4-benzodioxan-6-base ketone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.61(s，6H)，7.23(d，1H)，8.01-8.03(m，2H)

(5) will contain 0.25g α-nitrine sec.-propyl 2,2,3,3-tetrafluoro-1, the mixture of 4-benzodioxan-6-base ketone, 15ml methyl alcohol and 13mg 5% palladium on carbon at room temperature reacted 1 hour in nitrogen atmosphere.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates, and obtains the buttery alpha-amino group sec.-propyl 2,2,3 of 0.23g, 3-tetrafluoro-1,4-benzodioxan-6-base ketone.

(6) the triethylamine adding with 0.16g contains 0.23g alpha-amino group sec.-propyl 2,2,3,3-tetrafluoro-1, in the mixture of 4-benzodioxan-6-base ketone and 10ml tetrahydrofuran (THF), and, at room temperature reacted then 3 hours with ice-cooled following to wherein being added dropwise to the mixture that contains 0.13g 3-methyl-2-thiophene carbonyl chlorine and 5ml tetrahydrofuran (THF).With the reaction mixture ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=1/4), the fusing point that obtains 0.23g is 120-122 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.76(s，6H)，2.39(s，3H)，6.54(s，1H)，6.84(d，1H)，7.24(d，1H)，7.42(d，1H)，7.84(s，1H)，7.96(s，1H)

Preparation embodiment 5

Preparation N-[(3 ', 4 '-two chloro-1,1-dimethyl) phenacyl]-3-methyl-2-thenoyl amine (following compound N is o.1-20)

The 303mg triethylamine is added the alpha-amino group-3 that contains 268mg according to the acquisition of the technology (1) to (5) among the above-mentioned preparation embodiment 1, in the mixture of 4-dichloro isobutyl phenenyl keto hydrochloride and 5ml tetrahydrofuran (THF), and with ice-cooled down to wherein dripping the mixture that contains 265mg 3-methyl-2-thiophene carbonyl chlorine and 2.5ml tetrahydrofuran (THF).After finishing dropping, this mixture was in room temperature reaction 3 hours.The reaction mixture ethyl acetate extraction washes with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=1/3), the fusing point that obtains 180mg is 141 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.72(s，6H)，2.37(s，3H)，6.53(s，1H)，6.85(d，1H)，7.25(d，1H)，7.43(d，1H)，7.86(dd，1H)，8.13(s，1H)

Preparation embodiment 6

Preparation N-[(4 '-methoxyl group-2 '-methyl isophthalic acid, the 1-dimethyl) phenacyl]-3-methyl-2-thenoyl amine (following compound N is o.1-160)

(1) mixture that will contain 5.7g isobutyl chloride and 5ml dithiocarbonic anhydride is added drop-wise in the mixture that contains 7.15g aluminum chloride and 20ml dithiocarbonic anhydride under maximum 10 ℃, reacts then 0.5 hour.Then, contain the mixture of 5.0g meta-cresol and 5ml dithiocarbonic anhydride, then in room temperature reaction 4 hours in maximum 5 ℃ of droppings.Reaction mixture is put into the mixture of frozen water and hydrochloric acid, use dichloromethane extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.In resistates, adding 60ml tetrahydrofuran (THF), 30ml water and 3.7g sodium hydroxide, then in room temperature reaction 1.5 hours. reaction mixture under reduced pressure concentrates, and puts into frozen water then, and is adjusted to slightly acidic with dilute sulphuric acid, uses ethyl acetate extraction then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/9), obtain the solid 4-hydroxy-2-methyl isobutyl phenyl ketone of 2.45g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.15(d，6H)，2.43(s，3H)，3.40(m，1H)，6.70(m，2H)，7.57(d，1H)

(2) mixture that will contain 0.62g methyl-sulfate and 3ml dimethyl formamide adds and to contain in the mixture of 0.8g 4-hydroxy-2-methyl-isobutyl phenyl ketone, 0.68g salt of wormwood and 15ml dimethyl formamide, then in room temperature reaction 3 hours.Reaction mixture is put into water, and use ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is purified (developping agent ethyl acetate/normal hexane=1/9) by silica gel column chromatography, obtains oily 4-methoxyl group-2-methyl-isobutyl phenyl ketone of 0.59g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.13(d，6H)，2.46(s，1H)，3.38(m，1H)，6.72(m，2H)，7.59(d，1H)

(3) the phenyl trimethylammonium tribromide ammonium adding with 1.16g contains in the mixture of 0.59g 4-methoxyl group-2-methyl-isobutyl phenyl ketone and 15ml tetrahydrofuran (THF), at room temperature reacts then 2.5 hours.In reaction mixture, add ether, and leach insoluble substance.Filtrate under reduced pressure concentrates, and obtains buttery α-bromo-4-methoxyl group-2-methyl-isobutyl phenyl ketone of 0.7g.

(4) the sodiumazide adding with 0.4g contains in the mixture of 0.7g α-bromo-4-methoxyl group-2-methyl-isobutyl phenyl ketone and 8ml dimethyl sulfoxide (DMSO), then in 50 ℃ of reactions 1.5 hours.Reaction mixture is put into water, and use ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/9), obtain buttery α-nitrine-4-methoxyl group-2-methyl-isobutyl phenyl ketone of 0.67g.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.54(s，6H)，2.33(s，1H)，3.81(s，3H)，6.72(dd，1H)，6.75(d，1H)，7.61(d，1H)

(5) mixture that will contain 0.25g α-nitrine-4-methoxyl group-2-methyl-isobutyl phenyl ketone, 10ml methyl alcohol and 13mg 5% palladium on carbon at room temperature reacted 3 hours in nitrogen atmosphere.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates, and obtains buttery alpha-amino group-4-methoxyl group-2-methyl-isobutyl phenyl ketone of 0.23g.

(6) triethylamine of 0.13g added contain in the mixture of 0.22g alpha-amino group-4-methoxyl group-2-methyl-isobutyl phenyl ketone and 12ml tetrahydrofuran (THF), and with ice-cooled time to wherein being added dropwise to the mixture that contains 0.17g 3-methyl-2-thiophene carbonyl chlorine and 3ml tetrahydrofuran (THF).After finishing dropping, this mixture at room temperature reacted 2 hours.With the reaction mixture ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=1/3), the fusing point that obtains 0.35g is 99-101 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.77(s，6H)，2.38(s，3H)，2.45(s，3H)，6.81(dd，1H)，6.71(s，1H)，6.85(m，2H)，7.26(d，1H)，7.49(d，1H)

Preparation embodiment 7

Preparation N-[(3 ', 4 '-dimethoxy-1,1-dimethyl) phenacyl]-3-methyl-2-thenoyl amine (following compound N is o.1-535)

(1) the sec.-propyl bromination magnesium ethereal solution that will use 5.6g 2-N-PROPYLE BROMIDE, 0.94g magnesium and 30ml ether to prepare is added drop-wise to and contains 5.0g 3, in the mixture of 4-dimethoxy benzaldehyde and 50ml ether, reacts 15 hours under refluxing then.Reaction mixture is put into frozen water, add dilute sulphuric acid, stir then.This mixture dichloromethane extraction washes with water then.The organic layer anhydrous sodium sulfate drying under reduced pressure concentrates then, obtains buttery 1-(3 ', 4 '-Dimethoxyphenyl)-2-methylpropanol of 6.3g.

(2) mixture that will contain 6.28g 1-(3 ', 4 '-Dimethoxyphenyl)-2-methylpropanol and 30ml methylene dichloride adds and to contain in the mixture of 6.5g pyridinium chlorochromate, 4.9g sodium acetate and 100ml methylene dichloride, then room temperature reaction 15 hours.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=3/7), obtain the buttery 3 of 3.9g, 4-dimethoxy isobutyl phenyl ketone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.70(d，6H)，3.50(m，1H)，3.89(s，3H)，3.90(s，3H)，6.85(d，1H)，7.50(d，1H)，7.56(dd，1H)

(3) the phenyl trimethylammonium tribromide ammonium adding with 1.81g contains 1.0g 3, in the mixture of 4-dimethoxy isobutyl phenyl ketone and 20ml tetrahydrofuran (THF), at room temperature reacts then 2 hours.In reaction mixture, add ether, and leach insoluble substance.Filtrate under reduced pressure concentrates, and obtains buttery α-bromo-3,4-dimethoxy isobutyl phenyl ketone.

(4) the sodiumazide adding with 0.62g contains α-bromo-3, in the mixture of 4-dimethoxy isobutyl phenyl ketone and 20ml dimethyl sulfoxide (DMSO), then in 50 ℃ of reactions 1.5 hours.Reaction mixture is put into water, and use ethyl acetate extraction, wash with water then.The organic layer anhydrous magnesium sulfate drying under reduced pressure concentrates then.Resistates is by silica gel column chromatography purification (developping agent: ethyl acetate/normal hexane=1/4), obtain buttery α-nitrine-3 of 1.1g, 4-dimethoxy isobutyl phenyl ketone.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 400MHz)

1.56(s，6H)，3.91(s，3H)，3.93(s，3H)，6.86(d，1H)，7.62(d，1H)，7.94(dd，1H)

(5) will contain 0.25g α-nitrine-3, the mixture of 4-dimethoxy isobutyl phenyl ketone, 15ml methyl alcohol and 13mg 5% palladium on carbon at room temperature reacted 3 hours in nitrogen atmosphere.This reaction mixture filters with C salt, and filtrate under reduced pressure concentrates, and obtains the oily alpha-amino group-3 of 0.2g, 4-dimethoxy isobutyl phenyl ketone.

(6) the triethylamine adding with 0.11g contains 0.2g alpha-amino group-3,4-dimethoxy isobutyl phenyl ketone and 12ml 1, in the mixture of 2-ethylene dichloride, and containing 0.14g 3-methyl-2-thiophene carbonyl chlorine and 2ml 1 to wherein being added dropwise to, the mixture of 2-ethylene dichloride down with ice-cooled.After finishing dropping, this mixture at room temperature reacted 1.5 hours.With the reaction mixture dichloromethane extraction, wash with water then.The organic layer anhydrous sodium sulfate drying under reduced pressure concentrates then.Resistates is purified by silica gel column chromatography, and (developping agent: ethyl acetate/normal hexane=3/2), the fusing point that obtains 0.1g is 138-140 ℃ a required product.The NMR spectrum data of this product are as follows.

¹H-NMR δ ppm (solvent: CDCl ₃/ 300MHz)

1.82(s，6H)，2.44(s，3H)，3.89(s，6H)，6.80(d，1H)，6.85(d，1H)，6.88(s，1H)，7.23(d，1H)，7.63(d，1H)，7.75(dd，1H)

Now, in table 1-9, formula (I), the amide derivatives of (I-α) or the exemplary of its salt are described.These compounds can be according to preparation embodiment or by above-mentioned prepared in various methods.

In table, No. represents compound number, and Me represents methyl, and Et represents ethyl, and Pr (i) represents sec.-propyl, and P (n) represents n-propyl, and Bu (t) represents the tertiary butyl, and Bu (n) represents normal-butyl, and Bu (sec) represents sec-butyl, and CO represents carbonyl, CO ₂The expression carboxyl, Ph represents phenyl.In addition, in these tables, Ph (4-Cl) is illustrated in the phenyl that is replaced by the chlorine atom on the 4-position, and Ph (3,4-Cl ₂) be illustrated in the phenyl that is replaced by the chlorine atom on 3-position and the 4-position.This also is applicable to other statement.In addition, used abbreviation D1 to D7 and B1 to B117 represents following substituting group respectively in table.

Table 1

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-31	Me	Me	3-OCHF ₂	B21	110
1-32	Me	Me	4-Cl	B21	175	1-31	Me	Me	3-OCHF ₂	B21	110
1-32	Me	Me	4-Cl	B21	175	1-33	Me	Me	3-Cl-4-Cl	B9	126-130
1-34	Me	Me	H	B1	103-105	1-33	Me	Me	3-Cl-4-Cl	B9	126-130
1-34	Me	Me	H	B1	103-105	1-35	Me	Me	4-Br	B19	235-240
1-36	Me	Me	4-Br	B16	183-185	1-35	Me	Me	4-Br	B19	235-240
1-36	Me	Me	4-Br	B16	183-185	1-37	Me	Me	4-Br	B20	245-247
1-38	Me	Me	3-Cl	B2	141-142	1-37	Me	Me	4-Br	B20	245-247
1-38	Me	Me	3-Cl	B2	141-142	1-39	Me	Me	4-Cl	B2	140-141
1-40	Me	Me	3-Cl-4-Cl	B12	225-227	1-39	Me	Me	4-Cl	B2	140-141
1-40	Me	Me	3-Cl-4-Cl	B12	225-227	1-41	Me	Me	3-Cl-4-Cl	B5	171-172
1-42	Me	Me	3-F-4-F	B1	134-136	1-41	Me	Me	3-Cl-4-Cl	B5	171-172
1-42	Me	Me	3-F-4-F	B1	134-136	1-43	Me	Me	3-F-4-F	B16	150-152
1-44	Me	Me	2-Cl	B1	144-145	1-43	Me	Me	3-F-4-F	B16	150-152
1-44	Me	Me	2-Cl	B1	144-145	1-45	Me	Me	2-Cl	B16	130-132
1-46	Me	Me	3-Cl-4-Cl	B6	Solid	1-45	Me	Me	2-Cl	B16	130-132
1-46	Me	Me	3-Cl-4-Cl	B6	Solid	1-47	Me	Me	3-Cl-4-Cl	B4	150-152
1-48	Me	Me	3-Cl-4-Cl	B27	140-141	1-47	Me	Me	3-Cl-4-Cl	B4	150-152
1-48	Me	Me	3-Cl-4-Cl	B27	140-141	1-49	Me	Me	3-Cl-4-Cl	B3	141-146
1-50	Me	Me	3-Cl-4-Cl	B10		1-49	Me	Me	3-Cl-4-Cl	B3	141-146
1-50	Me	Me	3-Cl-4-Cl	B10		1-51	Me	Me	3-Cl-4-Cl	B11
1-52	Me	Me	4-Br	B1	183-185	1-51	Me	Me	3-Cl-4-Cl	B11
1-52	Me	Me	4-Br	B1	183-185	1-53	Me	Me	3-Cl-5-Cl	B16	168-170
1-54	Me	Me	3-Cl-5-Cl	B1	152-153	1-53	Me	Me	3-Cl-5-Cl	B16	168-170
1-54	Me	Me	3-Cl-5-Cl	B1	152-153	1-55	Me	Me	3-Br	B16	143-145
1-56	Me	Me	3-Br	B1	151-152	1-55	Me	Me	3-Br	B16	143-145
1-56	Me	Me	3-Br	B1	151-152	1-57	Me	Me	3-Cl-4-Cl	B15	175-178
1-58	Me	Me	3-Cl-4-Cl	B17		1-57	Me	Me	3-Cl-4-Cl	B15	175-178
1-58	Me	Me	3-Cl-4-Cl	B17		1-59	Me	Me	3-Cl-4-Cl	B18
1-60	Me	Me	2-Cl-4-Cl	B16	165-167	1-59	Me	Me	3-Cl-4-Cl	B18
1-60	Me	Me	2-Cl-4-Cl	B16	165-167	1-61	Me	Me	2-Cl-4-Cl	B1	170-171

Table 1 (continuing)

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-96	Me	Me	4-NO ₂	B21	135-137
1-97	Me	Me	3-Me-4-Me	B1	130-132	1-96	Me	Me	4-NO ₂	B21	135-137
1-97	Me	Me	3-Me-4-Me	B1	130-132	1-98	Me	Me	2-Me-4-OCHF ₂	B21	112-114
1-99	Me	Me	3-Cl-5-Cl	B21	137-140	1-98	Me	Me	2-Me-4-OCHF ₂	B21	112-114
1-99	Me	Me	3-Cl-5-Cl	B21	137-140	1-100	Me	Me	3-Cl-4-Br	B21	120-121
1-101	Me	Me	3-Me-4-Cl	B21	108-112	1-100	Me	Me	3-Cl-4-Br	B21	120-121
1-101	Me	Me	3-Me-4-Cl	B21	108-112	1-102	Me	Me	3-Br-4-Cl	B21	117-120
1-103	Me	Me	3-Cl-4-Me	B21	115-118	1-102	Me	Me	3-Br-4-Cl	B21	117-120
1-103	Me	Me	3-Cl-4-Me	B21	115-118	1-104	Me	Me	2-Me-4-F	B21	107-109
1-105	Me	Me	4-Me	B21	152-154	1-104	Me	Me	2-Me-4-F	B21	107-109
1-105	Me	Me	4-Me	B21	152-154	1-106	Me	Me	4-OCF ₃	B21	116-120
1-107	Me	Me	3-Br-4-OCF ₃	B21	107-111	1-106	Me	Me	4-OCF ₃	B21	116-120
1-107	Me	Me	3-Br-4-OCF ₃	B21	107-111	1-108	Me	Me	3-CF ₃-4-Cl	B21	133-135
1-109	Me	Me	3-Cl-4-Br	B1	105-109	1-108	Me	Me	3-CF ₃-4-Cl	B21	133-135
1-109	Me	Me	3-Cl-4-Br	B1	105-109	1-110	Me	Me	3-Cl-4-Cl	B19	192-195
1-111	Me	Me	4-OCH ₂CF ₃	B21	134-138	1-110	Me	Me	3-Cl-4-Cl	B19	192-195
1-111	Me	Me	4-OCH ₂CF ₃	B21	134-138	1-112	Me	Me	4-OCHF ₂	B21	118-120
1-113	Me	Me	3-OMe-4-Cl	B21	154-159	1-112	Me	Me	4-OCHF ₂	B21	118-120
1-113	Me	Me	3-OMe-4-Cl	B21	154-159	1-114	Me	Me	3-Me-4-OCF ₃	B21	116-118
1-115	Me	Me	3-Cl-4-Me-5-Me	B21	107-114	1-114	Me	Me	3-Me-4-OCF ₃	B21	116-118
1-115	Me	Me	3-Cl-4-Me-5-Me	B21	107-114	1-116	Me	Me	2-Cl-3-Cl-4-Cl	B1	133-137
1-117	Me	Me	2-Me-3-Cl-4-Cl	B1	94-98	1-116	Me	Me	2-Cl-3-Cl-4-Cl	B1	133-137
1-117	Me	Me	2-Me-3-Cl-4-Cl	B1	94-98	1-118	Me	Me	2-Cl-3-Cl-4-Cl	B21	112-115
1-119	Me	Me	2-Me-3-Cl-4-Cl	B21	90-95	1-118	Me	Me	2-Cl-3-Cl-4-Cl	B21	112-115
1-119	Me	Me	2-Me-3-Cl-4-Cl	B21	90-95	1-120	Me	Me	2-Me-3-Me-4-Cl	B21	Oil
1-121	Me	Me	2-Cl-3-Me-4-Me	B21	Oil	1-120	Me	Me	2-Me-3-Me-4-Cl	B21	Oil
1-121	Me	Me	2-Cl-3-Me-4-Me	B21	Oil	1-122	Me	Me	3-Cl-4-Cl	B8	200-202
1-123	Me	H	4-Cl	B16	Oil	1-122	Me	Me	3-Cl-4-Cl	B8	200-202
1-123	Me	H	4-Cl	B16	Oil	1-124	Me	Me	4-Br	B39	126-129
1-125	Me	Me	4-Bu(t)	B21	130-134	1-124	Me	Me	4-Br	B39	126-129
1-125	Me	Me	4-Bu(t)	B21	130-134	1-126	Me	Me	4-Bu(t)	B1	161-165
1-127	Me	Me	3-Me-4-Cl	B21	108-112	1-126	Me	Me	4-Bu(t)	B1	161-165
1-127	Me	Me	3-Me-4-Cl	B21	108-112	1-128	Me	Me	3-Cl-4-Cl	B37	157-159
1-129	Me	Me	3-Cl-4-Cl	B43	120-125	1-128	Me	Me	3-Cl-4-Cl	B37	157-159
1-129	Me	Me	3-Cl-4-Cl	B43	120-125	1-130	Me	Me	3-Cl-4-Cl	B44	165-170

Table 1 (continuing)

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-166	Me	Me	2-Br-4-CF ₃	B21	90-92
1-167	Me	Me	3-Br-4-Br	B21	127-130	1-166	Me	Me	2-Br-4-CF ₃	B21	90-92
1-167	Me	Me	3-Br-4-Br	B21	127-130	1-168	Me	Me	3-Me-4-OCHF ₂	B21	100-106
1-169	Me	Me	4-[D3]	B21	107-109	1-168	Me	Me	3-Me-4-OCHF ₂	B21	100-106
1-169	Me	Me	4-[D3]	B21	107-109	1-170	Me	Me	3-Cl-4-Cl	B59	139-145
1-171	Me	Me	3-Cl-4-Cl	B60	139-141	1-170	Me	Me	3-Cl-4-Cl	B59	139-145
1-171	Me	Me	3-Cl-4-Cl	B60	139-141	1-172	Me	Me	3-Cl-4-Cl	B61	140-142
1-173	H	H	4-Cl	B21	119-121	1-172	Me	Me	3-Cl-4-Cl	B61	140-142
1-173	H	H	4-Cl	B21	119-121	1-174	Me	Me	2-Me-4-OPr	B21	97-100
1-175	Me	Me	3-Cl-4-Cl	B62	89-92	1-174	Me	Me	2-Me-4-OPr	B21	97-100
1-175	Me	Me	3-Cl-4-Cl	B62	89-92	1-176	Me	Me	3-Me-4-OMe	B21	123-125
1-177	Me	Me	3-Cl-4-OMe	B21	161-164	1-176	Me	Me	3-Me-4-OMe	B21	123-125
1-177	Me	Me	3-Cl-4-OMe	B21	161-164	1-178	Me	Me	2-Me-3-Me-4-OMe	B21	88-90
1-179	Me	Me	2-Me-3-Me-4-OCHF ₂	B21	Oil	1-178	Me	Me	2-Me-3-Me-4-OMe	B21	88-90
1-179	Me	Me	2-Me-3-Me-4-OCHF ₂	B21	Oil	1-180	Me	Me	4-OMe	B21	139-141
1-181	Me	Me	2-Me-4-OCOPr(i)	B21	Anhydrous	1-180	Me	Me	4-OMe	B21	139-141
1-181	Me	Me	2-Me-4-OCOPr(i)	B21	Anhydrous	1-182	Me	Me	2-Me-4-OH	B21	204-208
1-183	Me	Me	2-Me-4-OSO ₂Me	B21	81-84	1-182	Me	Me	2-Me-4-OH	B21	204-208
1-183	Me	Me	2-Me-4-OSO ₂Me	B21	81-84	1-184	Me	Me	2-OMe	B21	Oil
1-185	Me	Me	2-Me-3-OMe	B21	128-129	1-184	Me	Me	2-OMe	B21	Oil
1-185	Me	Me	2-Me-3-OMe	B21	128-129	1-186	Me	Me	2-Me-4-OBu(n)	B21	69-71
1-187	Me	Me	2-Me-4-OCH ₂CF ₃	B21	Oil	1-186	Me	Me	2-Me-4-OBu(n)	B21	69-71
1-187	Me	Me	2-Me-4-OCH ₂CF ₃	B21	Oil	1-188	Me	Me	2-Me-4-OCH ₂CH ₂OMe	B21	73-75
1-189	Me	H	4-Cl	B21	Oil	1-188	Me	Me	2-Me-4-OCH ₂CH ₂OMe	B21	73-75
1-189	Me	H	4-Cl	B21	Oil	1-190	Me	Me	2-Me-4-OPr(i)	B21	96-98
1-191	Me	Me	4-Br	B48		1-190	Me	Me	2-Me-4-OPr(i)	B21	96-98
1-191	Me	Me	4-Br	B48		1-192	Me	Me	4-Br	B49
1-193	Me	Me	4-Br	B50	122-125	1-192	Me	Me	4-Br	B49
1-193	Me	Me	4-Br	B50	122-125	1-194	Me	Me	4-Br	B51
1-195	Me	Me	4-Br	B52	192-195	1-194	Me	Me	4-Br	B51
1-195	Me	Me	4-Br	B52	192-195	1-196	Me	Me	4-Br	B53
1-197	Me	Me	4-Br	B54		1-196	Me	Me	4-Br	B53
1-197	Me	Me	4-Br	B54		1-198	Me	Me	4-Br	B13
1-199	Me	Me	4-Br	B12		1-198	Me	Me	4-Br	B13
1-199	Me	Me	4-Br	B12		1-200	Me	Me	4-Br	B63	132-134

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-201	Me	Me	4-Br	B55	164-166
1-202	Me	Me	4-Br	B56	145-147	1-201	Me	Me	4-Br	B55	164-166
1-202	Me	Me	4-Br	B56	145-147	1-203	Me	Me	4-Br	B57	45-47
1-204	Me	Me	4-Br	B57	50-58	1-203	Me	Me	4-Br	B57	45-47
1-204	Me	Me	4-Br	B57	50-58	1-205	Me	Me	3-F-4-Cl	B21	119-122
1-206	Me	Me	2-Me-4-Et	B21	77-81	1-205	Me	Me	3-F-4-Cl	B21	119-122
1-206	Me	Me	2-Me-4-Et	B21	77-81	1-207	Et	H	4-Cl	B21	114-117
1-208	Me	Me	2-Cl-4-Cl	B21	103-104	1-207	Et	H	4-Cl	B21	114-117
1-208	Me	Me	2-Cl-4-Cl	B21	103-104	1-209	Me	Me	3-OCHF ₂-4-Cl	B21	106-110
1-210	Me	Me	3-Cl-4-OCHF ₂	B21	137-139	1-209	Me	Me	3-OCHF ₂-4-Cl	B21	106-110
1-210	Me	Me	3-Cl-4-OCHF ₂	B21	137-139	1-211	Me	Me	3-Cl-4-Cl	B63
1-212	Me	Me	3-Cl-4-Cl	B64		1-211	Me	Me	3-Cl-4-Cl	B63
1-212	Me	Me	3-Cl-4-Cl	B64		1-213	Me	Me	3-Cl-4-Cl	B65
1-214	Me	Me	3-Cl-4-Cl	B66		1-213	Me	Me	3-Cl-4-Cl	B65
1-214	Me	Me	3-Cl-4-Cl	B66		1-215	Me	Me	3-Cl-4-Cl	B67
1-216	Me	Me	3-Cl-4-Cl	B68		1-215	Me	Me	3-Cl-4-Cl	B67
1-216	Me	Me	3-Cl-4-Cl	B68		1-217	Me	Me	3-Cl-4-Cl	B69
1-218	Me	Me	3-Cl-4-Cl	B70		1-217	Me	Me	3-Cl-4-Cl	B69
1-218	Me	Me	3-Cl-4-Cl	B70		1-219	Me	Me	3-Cl-4-Cl	B71	122-124
1-220	Me	Me	3-Cl-4-Cl	B72		1-219	Me	Me	3-Cl-4-Cl	B71	122-124
1-220	Me	Me	3-Cl-4-Cl	B72		1-221	Me	Me	3-Cl-4-Cl	B73
1-222	Me	Me	3-Cl-4-Cl	B74		1-221	Me	Me	3-Cl-4-Cl	B73
1-222	Me	Me	3-Cl-4-Cl	B74		1-223	Me	Me	3-Cl-4-Cl	B75
1-224	Me	Me	3-Cl-4-Cl	B76		1-223	Me	Me	3-Cl-4-Cl	B75
1-224	Me	Me	3-Cl-4-Cl	B76		1-225	Me	Me	3-Cl-4-Cl	B77
1-226	Me	Me	3-Cl-4-Cl	B78		1-225	Me	Me	3-Cl-4-Cl	B77
1-226	Me	Me	3-Cl-4-Cl	B78		1-227	Me	Me	2-Me-4-O-[D3]	B21
1-228	Me	Me	2-Me-4-CH ₂NMe ₂	B21		1-227	Me	Me	2-Me-4-O-[D3]	B21
1-228	Me	Me	2-Me-4-CH ₂NMe ₂	B21		1-229	Me	Me	2-Me-4-CH ₂OMe	B21
1-230	Me	Me	2-Me-4-CH ₂SMe	B21		1-229	Me	Me	2-Me-4-CH ₂OMe	B21
1-230	Me	Me	2-Me-4-CH ₂SMe	B21		1-231	Me	Me	2-Me-5-OMe	B21	Oil
1-232	Me	Me	2-Me-5-Cl	B21		1-231	Me	Me	2-Me-5-OMe	B21	Oil
1-232	Me	Me	2-Me-5-Cl	B21		1-233	Me	Me	2-Me-6-OMe	B21
1-234	Me	Me	2-Me-6-Me	B21		1-233	Me	Me	2-Me-6-OMe	B21
1-234	Me	Me	2-Me-6-Me	B21		1-235	Me	Me	2-Me-4-OMe-6-Me	B21

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-236	Me	Me	2-Me-4-Br	B21
1-237	Me	Me	2-Me-4-OCF ₂CHF ₂	B21		1-236	Me	Me	2-Me-4-Br	B21
1-237	Me	Me	2-Me-4-OCF ₂CHF ₂	B21		1-238	Me	Me	2-Me-4-OCH ₂CF ₂CF ₃	B21
1-239	Me	Me	2-Me-4-OCF ₂CHFCF ₃	B21		1-238	Me	Me	2-Me-4-OCH ₂CF ₂CF ₃	B21
1-239	Me	Me	2-Me-4-OCF ₂CHFCF ₃	B21		1-240	Me	Me	2-Et-4-OMe	B21
1-241	Me	Me	2-CF ₃-4-OMe	B21		1-240	Me	Me	2-Et-4-OMe	B21
1-241	Me	Me	2-CF ₃-4-OMe	B21		1-242	Me	Me	2-CF ₃-4-Cl	B21
1-243	Me	Me	3-Me-4-Br	B21		1-242	Me	Me	2-CF ₃-4-Cl	B21
1-243	Me	Me	3-Me-4-Br	B21		1-244	Me	Me	3-Br-4-Me	B21	118-120
1-245	Me	Me	2-Me-4-OCH ₂CN	B21		1-244	Me	Me	3-Br-4-Me	B21	118-120
1-245	Me	Me	2-Me-4-OCH ₂CN	B21		1-246	Me	Me	2-Me-4-NHCH ₂CN	B21
1-247	Me	Me	2-Me-4-SCH ₂CN	B21		1-246	Me	Me	2-Me-4-NHCH ₂CN	B21
1-247	Me	Me	2-Me-4-SCH ₂CN	B21		1-248	Me	Me	2-Me-4-OCH ₂-[D3]	B21
1-249	Me	Me	2-Me-4-NHCH ₂-[D3]	B21		1-248	Me	Me	2-Me-4-OCH ₂-[D3]	B21
1-249	Me	Me	2-Me-4-NHCH ₂-[D3]	B21		1-250	Me	Me	2-Me-4-SCH ₂-[D3]	B21
1-251	Me	Me	2-Me-4-SMe	B21		1-250	Me	Me	2-Me-4-SCH ₂-[D3]	B21
1-251	Me	Me	2-Me-4-SMe	B21		1-252	Me	Me	2-Me-4-SOMe	B21
1-253	Me	Me	2-Me-4-SO ₂Me	B21		1-252	Me	Me	2-Me-4-SOMe	B21
1-253	Me	Me	2-Me-4-SO ₂Me	B21		1-254	Me	Me	2-Me-4-CHO	B21
1-255	Me	Me	2-Me-4-OCF ₃	B21		1-254	Me	Me	2-Me-4-CHO	B21
1-255	Me	Me	2-Me-4-OCF ₃	B21		1-256	Me	Me	2-Me-4-CHF ₂	B21
1-257	Me	Me	2-Me-4-CH ₂-[D3]	B21		1-256	Me	Me	2-Me-4-CHF ₂	B21
1-257	Me	Me	2-Me-4-CH ₂-[D3]	B21		1-258	Me	Me	2-Me-4-[D3]	B21
1-259	Me	Me	2-OCHF ₂-4-Cl	B21		1-258	Me	Me	2-Me-4-[D3]	B21
1-259	Me	Me	2-OCHF ₂-4-Cl	B21		1-260	Me	Me	2-F-4-Cl	B21
1-261	Me	Me	2-OMe-4-Cl	B21		1-260	Me	Me	2-F-4-Cl	B21
1-261	Me	Me	2-OMe-4-Cl	B21		1-262	Me	Me	2-Me-4-CH ₂OCOMe	B21
1-263	Me	Me	2-Me-4-CH ₂OH	B21		1-262	Me	Me	2-Me-4-CH ₂OCOMe	B21
1-263	Me	Me	2-Me-4-CH ₂OH	B21		1-264	Me	Me	2-Me-4-CH ₂Br	B21
1-265	Me	Me	2-Me-4-I	B21		1-264	Me	Me	2-Me-4-CH ₂Br	B21
1-265	Me	Me	2-Me-4-I	B21		1-266	Me	Me	2-Me-3-OEt	B21
1-267	Me	Me	The 2-Me-4-cyclopentyloxy	B21		1-266	Me	Me	2-Me-3-OEt	B21
1-267	Me	Me	The 2-Me-4-cyclopentyloxy	B21		1-268	Me	Me	2-Me-4-Ph	B21	97-102
1-269	Me	Me	2-Me-4-OPh	B21		1-268	Me	Me	2-Me-4-Ph	B21	97-102
1-269	Me	Me	2-Me-4-OPh	B21		1-270	Me	Me	2-Me-4-OCOMe	B21	Oil

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-271	Me	Me	2-Me-4-C≡CCMe ₃	B21	Anhydrous
1-272	Me	Me	2-Me-4-OCH ₂C≡CH	B21		1-271	Me	Me	2-Me-4-C≡CCMe ₃	B21	Anhydrous
1-272	Me	Me	2-Me-4-OCH ₂C≡CH	B21		1-273	Me	Me	2-Me-4-OBu(sec)	B21	Viscosity
1-274	Me	Me	2-Me-4-OCH([D3])Me	B21		1-273	Me	Me	2-Me-4-OBu(sec)	B21	Viscosity
1-274	Me	Me	2-Me-4-OCH([D3])Me	B21		1-275	Me	Me	2-Me-4-NH([D3])Me	B21
1-276	Me	Me	2-Me-4-C≡CPh	B21	Anhydrous	1-275	Me	Me	2-Me-4-NH([D3])Me	B21
1-276	Me	Me	2-Me-4-C≡CPh	B21	Anhydrous	1-277	Me	Me	2-Me-4-OCF ₂CHFOCF ₃	B21
1-278	Me	Me	2-Me-4-CN	B21		1-277	Me	Me	2-Me-4-OCF ₂CHFOCF ₃	B21
1-278	Me	Me	2-Me-4-CN	B21		1-279	Me	Me	2-Me-4-CH ₂C≡CCMe ₃	B21
1-280	Me	Me	2-Me-4-C≡CMe	B21		1-279	Me	Me	2-Me-4-CH ₂C≡CCMe ₃	B21
1-280	Me	Me	2-Me-4-C≡CMe	B21		1-281	Me	Me	2-Me-4-C≡CH	B21
1-282	Me	Me	2-Me-4-C≡CSiMe ₃	B21	Viscosity	1-281	Me	Me	2-Me-4-C≡CH	B21
1-282	Me	Me	2-Me-4-C≡CSiMe ₃	B21	Viscosity	1-283	Me	Me	2-Me-4-[D1]	B21
1-284	Me	Me	2-Me-4-[D2]	B21		1-283	Me	Me	2-Me-4-[D1]	B21
1-284	Me	Me	2-Me-4-[D2]	B21		1-285	Me	Me	2-Me-4-CH ₂C≡CI	B21
1-286	Me	Me	2-Me-4-CH ₂C≡CH	B21		1-285	Me	Me	2-Me-4-CH ₂C≡CI	B21
1-286	Me	Me	2-Me-4-CH ₂C≡CH	B21		1-287	Me	Me	2-Me-4-CH＝CF ₂	B21
1-288	Me	Me	2-Me-4-CH ₂CH＝CF ₂	B21		1-287	Me	Me	2-Me-4-CH＝CF ₂	B21
1-288	Me	Me	2-Me-4-CH ₂CH＝CF ₂	B21		1-289	Me	Me	2-Me-4-OCH ₂CH＝CCl ₂	B21
1-290	Me	Me	2-Me-4-CH ₂CH ₂CH＝CF ₂	B21		1-289	Me	Me	2-Me-4-OCH ₂CH＝CCl ₂	B21
1-290	Me	Me	2-Me-4-CH ₂CH ₂CH＝CF ₂	B21		1-291	Me	Me	2-Me-4-(CH ₂) ₅CBrF ₂	B21
1-292	Me	Me	2-Me-4-CH ₂C≡CI	B1		1-291	Me	Me	2-Me-4-(CH ₂) ₅CBrF ₂	B21
1-292	Me	Me	2-Me-4-CH ₂C≡CI	B1		1-293	Me	Et	3-Cl-4-Cl	B1
1-294	Me	Et	3-Me-4-Cl	B1		1-293	Me	Et	3-Cl-4-Cl	B1
1-294	Me	Et	3-Me-4-Cl	B1		1-295	Me	Et	2-Me-4-OMe	B1
1-296	Me	Et	2-Me-4-OEt	B1		1-295	Me	Et	2-Me-4-OMe	B1
1-296	Me	Et	2-Me-4-OEt	B1		1-297	Me	Et	2-Me-4-OPr(i)	B1
1-298	Me	Et	3-Cl-4-Br	B1		1-297	Me	Et	2-Me-4-OPr(i)	B1
1-298	Me	Et	3-Cl-4-Br	B1		1-299	Me	Et	3-Br-4-Cl	B1
1-300	Me	Et	3-F-4-Cl	B1		1-299	Me	Et	3-Br-4-Cl	B1
1-300	Me	Et	3-F-4-Cl	B1		1-301	Me	Et	3-Me-4-Br	B1
1-302	Et	Et	3-Cl-4-Cl	B1		1-301	Me	Et	3-Me-4-Br	B1
1-302	Et	Et	3-Cl-4-Cl	B1		1-303	Et	Et	3-Me-4-Cl	B1
1-304	Et	Et	2-Me-4-OEt	B1		1-303	Et	Et	3-Me-4-Cl	B1
1-304	Et	Et	2-Me-4-OEt	B1		1-305	Et	Et	2-Me-4-OPr(i)	B1

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-306	Me	Et	3-Cl-4-Cl	B16
1-307	Me	Et	3-Me-4-Cl	B16		1-306	Me	Et	3-Cl-4-Cl	B16
1-307	Me	Et	3-Me-4-Cl	B16		1-308	Me	Et	2-Me-4-OMe	B16
1-309	Me	Et	2-Me-4-OEt	B16		1-308	Me	Et	2-Me-4-OMe	B16
1-309	Me	Et	2-Me-4-OEt	B16		1-310	Me	Et	2-Me-4-OPr(i)	B16
1-311	Me	Et	3-Cl-4-Br	B16		1-310	Me	Et	2-Me-4-OPr(i)	B16
1-311	Me	Et	3-Cl-4-Br	B16		1-312	Me	Et	3-Br-4-Cl	B16
1-313	Me	Et	3-F-4-Cl	B16		1-312	Me	Et	3-Br-4-Cl	B16
1-313	Me	Et	3-F-4-Cl	B16		1-314	Me	Et	3-Me-4-Br	B16
1-315	Et	Et	3-Cl-4-Cl	B16		1-314	Me	Et	3-Me-4-Br	B16
1-315	Et	Et	3-Cl-4-Cl	B16		1-316	Et	Et	3-Me-4-Cl	B16
1-317	Et	Et	2-Me-4-OEt	B16		1-316	Et	Et	3-Me-4-Cl	B16
1-317	Et	Et	2-Me-4-OEt	B16		1-318	Et	Et	2-Me-4-OPr(i)	B16
1-319	Me	Et	3-Me-4-Cl	B21		1-318	Et	Et	2-Me-4-OPr(i)	B16
1-319	Me	Et	3-Me-4-Cl	B21		1-320	Me	Et	2-Me-4-OMe	B21
1-321	Me	Et	2-Me-4-OEt	B21		1-320	Me	Et	2-Me-4-OMe	B21
1-321	Me	Et	2-Me-4-OEt	B21		1-322	Me	Et	2-Me-4-OPr(i)	B21
1-323	Me	Et	3-Cl-4-Br	B21		1-322	Me	Et	2-Me-4-OPr(i)	B21
1-323	Me	Et	3-Cl-4-Br	B21		1-324	Me	Et	3-Br-4-Cl	B21
1-325	Me	Et	3-F-4-Cl	B21		1-324	Me	Et	3-Br-4-Cl	B21
1-325	Me	Et	3-F-4-Cl	B21		1-326	Me	Et	3-Me-4-Br	B21
1-327	Et	Et	3-Cl-4-Cl	B21		1-326	Me	Et	3-Me-4-Br	B21
1-327	Et	Et	3-Cl-4-Cl	B21		1-328	Et	Et	3-Me-4-Cl	B21
1-329	Et	Et	2-Me-4-OEt	B21		1-328	Et	Et	3-Me-4-Cl	B21
1-329	Et	Et	2-Me-4-OEt	B21		1-330	Et	Et	2-Me-4-OPr(i)	B21
1-331	Me	Me	3-Me-4-Cl	B71		1-330	Et	Et	2-Me-4-OPr(i)	B21
1-331	Me	Me	3-Me-4-Cl	B71		1-332	Me	Me	2-Me-4-OMe	B71
1-333	Me	Me	2-Me-4-OEt	B71		1-332	Me	Me	2-Me-4-OMe	B71
1-333	Me	Me	2-Me-4-OEt	B71		1-334	Me	Me	2-Me-4-OPr(i)	B71
1-335	Me	Me	3-Cl-4-Br	B71		1-334	Me	Me	2-Me-4-OPr(i)	B71
1-335	Me	Me	3-Cl-4-Br	B71		1-336	Me	Me	3-Br-4-Cl	B71
1-337	Me	Me	3-F-4-Cl	B71		1-336	Me	Me	3-Br-4-Cl	B71
1-337	Me	Me	3-F-4-Cl	B71		1-338	Me	Me	3-Me-4-Br	B71
1-339	Me	Me	2-Me-4-[D4]	B21		1-338	Me	Me	3-Me-4-Br	B71
1-339	Me	Me	2-Me-4-[D4]	B21		1-340	Me	Me	2-Me-4-[D5]	B21

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-341	Me	D3	3-Cl-4-Cl	B16
1-342	Me	D3	3-Me-4-Cl	B16		1-341	Me	D3	3-Cl-4-Cl	B16
1-342	Me	D3	3-Me-4-Cl	B16		1-343	Me	D3	2-Me-4-OMe	B16
1-344	Me	D3	2-Me-4-OEt	B16		1-343	Me	D3	2-Me-4-OMe	B16
1-344	Me	D3	2-Me-4-OEt	B16		1-345	Me	D3	2-Me-4-OPr(i)	B16
1-346	Me	D3	3-Cl-4-Br	B16		1-345	Me	D3	2-Me-4-OPr(i)	B16
1-346	Me	D3	3-Cl-4-Br	B16		1-347	Me	D3	3-Br-4-Cl	B16
1-348	Me	D3	3-F-4-Cl	B16		1-347	Me	D3	3-Br-4-Cl	B16
1-348	Me	D3	3-F-4-Cl	B16		1-349	Me	D3	3-Me-4-Br	B16
1-350	H	D3	3-Cl-4-Cl	B16		1-349	Me	D3	3-Me-4-Br	B16
1-350	H	D3	3-Cl-4-Cl	B16		1-351	H	D3	3-Me-4-Cl	B16
1-352	H	D3	2-Me-4-OMe	B16		1-351	H	D3	3-Me-4-Cl	B16
1-352	H	D3	2-Me-4-OMe	B16		1-353	H	D3	2-Me-4-OEt	B16
1-354	H	D3	2-Me-4-OPr(i)	B16		1-353	H	D3	2-Me-4-OEt	B16
1-354	H	D3	2-Me-4-OPr(i)	B16		1-355	Me	D3	3-Cl-4-Cl	B21
1-356	Me	D3	3-Me-4-Cl	B21		1-355	Me	D3	3-Cl-4-Cl	B21
1-356	Me	D3	3-Me-4-Cl	B21		1-357	Me	D3	2-Me-4-OMe	B21
1-358	Me	D3	2-Me-4-OEt	B21		1-357	Me	D3	2-Me-4-OMe	B21
1-358	Me	D3	2-Me-4-OEt	B21		1-359	Me	D3	2-Me-4-OPr(i)	B21
1-360	Me	D3	3-Cl-4-Br	B21		1-359	Me	D3	2-Me-4-OPr(i)	B21
1-360	Me	D3	3-Cl-4-Br	B21		1-361	Me	D3	3-Br-4-Cl	B21
1-362	Me	D3	3-F-4-Cl	B21		1-361	Me	D3	3-Br-4-Cl	B21
1-362	Me	D3	3-F-4-Cl	B21		1-363	Me	D3	3-Me-4-Br	B21
1-364	H	D3	3-Cl-4-Cl	B21		1-363	Me	D3	3-Me-4-Br	B21
1-364	H	D3	3-Cl-4-Cl	B21		1-365	H	D3	3-Me-4-Cl	B21
1-366	H	D3	2-Me-4-OMe	B21		1-365	H	D3	3-Me-4-Cl	B21
1-366	H	D3	2-Me-4-OMe	B21		1-367	H	D3	2-Me-4-OEt	B21
1-368	H	D3	2-Me-4-OPr(i)	B21		1-367	H	D3	2-Me-4-OEt	B21
1-368	H	D3	2-Me-4-OPr(i)	B21		1-369	Me	CH ₂F	3-Cl-4-Cl	B21
1-370	Me	CH ₂F	3-Me-4-Cl	B21		1-369	Me	CH ₂F	3-Cl-4-Cl	B21
1-370	Me	CH ₂F	3-Me-4-Cl	B21		1-371	Me	CH ₂Cl	2-Me-4-OMe	B21
1-372	Me	CH ₂F	2-Me-4-OEt	B21		1-371	Me	CH ₂Cl	2-Me-4-OMe	B21
1-372	Me	CH ₂F	2-Me-4-OEt	B21		1-373	Me	CH ₂F	2-Me-4-OPr(i)	B21
1-374	CH ₂F	CH ₂F	2-Me-4-OEt	B21		1-373	Me	CH ₂F	2-Me-4-OPr(i)	B21
1-374	CH ₂F	CH ₂F	2-Me-4-OEt	B21		1-375	CH ₂F	CH ₂F	2-Me-4-OPr(i)	B21

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-376	Me	Me	4-SMe	B16
1-377	Me	Me	4-SOMe	B16		1-376	Me	Me	4-SMe	B16
1-377	Me	Me	4-SOMe	B16		1-378	Me	Me	4-SO ₂Me	B16
1-379	Me	Me	4-SO ₂CF ₃	B16		1-378	Me	Me	4-SO ₂Me	B16
1-379	Me	Me	4-SO ₂CF ₃	B16		1-380	Me	Me	4-SO ₂NMe ₂	B16
1-381	Me	Me	4-CH ₂CH＝CH ₂	B16		1-380	Me	Me	4-SO ₂NMe ₂	B16
1-381	Me	Me	4-CH ₂CH＝CH ₂	B16		1-382	Me	Me	4-CH ₂NHMe	B16
1-383	Me	Me	2-Me-4-CH ₂NHMe	B21		1-382	Me	Me	4-CH ₂NHMe	B16
1-383	Me	Me	2-Me-4-CH ₂NHMe	B21		1-384	Me	Me	2-Me-4-OCH ₂CN	B21
1-385	Me	Me	2-Me-4-NHCH ₂CN	B21		1-384	Me	Me	2-Me-4-OCH ₂CN	B21
1-385	Me	Me	2-Me-4-NHCH ₂CN	B21		1-386	Me	Me	2-Me-4-SCH ₂CN	B21
1-387	Me	Me	4-OCH ₂CH＝CH ₂	B16		1-386	Me	Me	2-Me-4-SCH ₂CN	B21
1-387	Me	Me	4-OCH ₂CH＝CH ₂	B16		1-388	Me	Me	4-SCH ₂CH＝CH ₂	B16
1-389	Me	Me	4-OCH ₂C≡CH	B16		1-388	Me	Me	4-SCH ₂CH＝CH ₂	B16
1-389	Me	Me	4-OCH ₂C≡CH	B16		1-390	Me	Me	4-SCH ₂C≡CH	B16
1-391	Me	Me	4-OCH ₂C≡CI	B16		1-390	Me	Me	4-SCH ₂C≡CH	B16
1-391	Me	Me	4-OCH ₂C≡CI	B16		1-392	Me	Me	4-SCH ₂C≡CI	B16
1-393	Me	Me	2-Me-4-OCF ₂CHFOMe	B21		1-392	Me	Me	4-SCH ₂C≡CI	B16
1-393	Me	Me	2-Me-4-OCF ₂CHFOMe	B21		1-394	Me	Me	4-S-CH ₂CH＝CF ₂	B16
1-395	Me	Me	4-SOCHF ₂	B16		1-394	Me	Me	4-S-CH ₂CH＝CF ₂	B16
1-395	Me	Me	4-SOCHF ₂	B16		1-396	Me	Me	2-Me-4-CH ₂OCHF ₂	B21
1-397	Me	Me	2-Me-4-CH ₂NH ₂	B21		1-396	Me	Me	2-Me-4-CH ₂OCHF ₂	B21
1-397	Me	Me	2-Me-4-CH ₂NH ₂	B21		1-398	Me	Me	2-Me-4-SCHF ₂	B21
1-399	Me	Me	2-Me-4-SOCHF ₂	B21		1-398	Me	Me	2-Me-4-SCHF ₂	B21
1-399	Me	Me	2-Me-4-SOCHF ₂	B21		1-400	Me	Me	2-Me-4-SO ₂CHF ₂	B21
1-401	Me	Me	2-Me-4-OCH ₂CH ₂SMe	B21		1-400	Me	Me	2-Me-4-SO ₂CHF ₂	B21
1-401	Me	Me	2-Me-4-OCH ₂CH ₂SMe	B21		1-402	Me	Me	2-Me-4-OCH ₂CH ₂NHMe	B21
1-403	Me	Me	2-Me-4-OCH ₂CH ₂NMe ₂	B21		1-402	Me	Me	2-Me-4-OCH ₂CH ₂NHMe	B21
1-403	Me	Me	2-Me-4-OCH ₂CH ₂NMe ₂	B21		1-404	Me	Me	2-Me-4-NH-[D3]	B21
1-405	Me	Me	2-Me-4-S-[D3]	B21		1-404	Me	Me	2-Me-4-NH-[D3]	B21
1-405	Me	Me	2-Me-4-S-[D3]	B21		1-406	Me	Me	2-Me-4-OCH ₂CH ₂OCHF ₂	B71
1-407	Me	Me	4-CH＝NOCH ₂CH＝CH ₂	B1		1-406	Me	Me	2-Me-4-OCH ₂CH ₂OCHF ₂	B71
1-407	Me	Me	4-CH＝NOCH ₂CH＝CH ₂	B1		1-408	Me	Me	4-CH＝NOCH ₂C≡CH	B1
1-409	Me	Me	4-CH＝NCO ₂Me	B1		1-408	Me	Me	4-CH＝NOCH ₂C≡CH	B1
1-409	Me	Me	4-CH＝NCO ₂Me	B1		1-410	Me	Me	2-Me-4-CH＝NMe	B21

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-411	Me	Me	2-Me-4-CH＝N-OMe	B21
1-412	Me	Me	4-[D6]	B71		1-411	Me	Me	2-Me-4-CH＝N-OMe	B21
1-412	Me	Me	4-[D6]	B71		1-413	Me	Me	2-Me-4-OCOCF ₃	B21
1-414	Me	Me	2-Me-4-OCO ₂Me	B16		1-413	Me	Me	2-Me-4-OCOCF ₃	B21
1-414	Me	Me	2-Me-4-OCO ₂Me	B16		1-415	Me	Me	2-Me-4-OCONMe ₂	B16
1-416	Me	Me	2-Me-4-OCOSPh	B16		1-415	Me	Me	2-Me-4-OCONMe ₂	B16
1-416	Me	Me	2-Me-4-OCOSPh	B16		1-417	Me	Me	2-Me-4-OCSOMe	B14
1-418	Me	Me	2-Me-4-OCS ₂Me	B14		1-417	Me	Me	2-Me-4-OCSOMe	B14
1-418	Me	Me	2-Me-4-OCS ₂Me	B14		1-419	Me	Me	2-Me-4-OCSNMe ₂	B14
1-420	Me	Me	2-Me-4-OSCCl ₃	B14		1-419	Me	Me	2-Me-4-OCSNMe ₂	B14
1-420	Me	Me	2-Me-4-OSCCl ₃	B14		1-421	Me	Me	2-Me-4-OSO ₂Me	B14
1-422	Me	Me	2-Me-4-OSO ₂CF ₃	B14		1-421	Me	Me	2-Me-4-OSO ₂Me	B14
1-422	Me	Me	2-Me-4-OSO ₂CF ₃	B14		1-423	Me	Me	2-Me-4-OSO ₂Ph	B14
1-424	Me	Me	2-Me-4-OSNMe ₂	B14		1-423	Me	Me	2-Me-4-OSO ₂Ph	B14
1-424	Me	Me	2-Me-4-OSNMe ₂	B14		1-425	Me	Me	2-Me-4-OSO ₂NMe ₂	B14
1-426	Me	Me	2-Me-4-NH ₂	B14		1-425	Me	Me	2-Me-4-OSO ₂NMe ₂	B14
1-426	Me	Me	2-Me-4-NH ₂	B14		1-427	Me	Me	2-Me-4-NH ₂·HCl	B14
1-428	Me	Me	2-Me-4-NHMe	B14		1-427	Me	Me	2-Me-4-NH ₂·HCl	B14
1-428	Me	Me	2-Me-4-NHMe	B14		1-429	Me	Me	2-Me-4-NMe ₂	B14
1-430	Me	Me	2-Me-4-NHCOMe	B14		1-429	Me	Me	2-Me-4-NMe ₂	B14
1-430	Me	Me	2-Me-4-NHCOMe	B14		1-431	Me	Me	2-Me-4-NHCOBu(t)	B14
1-432	Me	Me	2-Me-4-NHCOCF ₃	B14		1-431	Me	Me	2-Me-4-NHCOBu(t)	B14
1-432	Me	Me	2-Me-4-NHCOCF ₃	B14		1-433	Me	Me	2-Me-4-NHCO ₂Me	B14
1-434	Me	Me	2-Me-4-N(Me)CO ₂Me	B14		1-433	Me	Me	2-Me-4-NHCO ₂Me	B14
1-434	Me	Me	2-Me-4-N(Me)CO ₂Me	B14		1-435	Me	Me	2-Me-4-NHCONMe ₂	B14
1-436	Me	Me	2-Me-4-NHCOSMe	B14		1-435	Me	Me	2-Me-4-NHCONMe ₂	B14
1-436	Me	Me	2-Me-4-NHCOSMe	B14		1-437	Me	Me	2-Me-4-NHCSOMe	B14
1-438	Me	Me	2-Me-4-NHCS ₂Me	B14		1-437	Me	Me	2-Me-4-NHCSOMe	B14
1-438	Me	Me	2-Me-4-NHCS ₂Me	B14		1-439	Me	Me	2-Me-4-NHCSNMe ₂	B14
1-440	Me	Me	2-Me-4-NHCS ₂Ph	B14		1-439	Me	Me	2-Me-4-NHCSNMe ₂	B14
1-440	Me	Me	2-Me-4-NHCS ₂Ph	B14		1-441	Me	Me	2-Me-4-NHSCCl ₃	B14
1-442	Me	Me	2-Me-4-NHSOMe	B14		1-441	Me	Me	2-Me-4-NHSCCl ₃	B14
1-442	Me	Me	2-Me-4-NHSOMe	B14		1-443	Me	Me	2-Me-4-NHSO ₂Me	B14
1-444	Me	Me	2-Me-4-NHSO ₂Ph	B14		1-443	Me	Me	2-Me-4-NHSO ₂Me	B14
1-444	Me	Me	2-Me-4-NHSO ₂Ph	B14		1-445	Me	Me	2-Me-4-NHCOPh	B14

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-481	Me	Me	3-Cl-4-Cl	B83
1-482	Me	Me	3-Me-4-Cl	B84		1-481	Me	Me	3-Cl-4-Cl	B83
1-482	Me	Me	3-Me-4-Cl	B84		1-483	Me	Me	2-Me-4-OMe	B85
1-484	Me	Me	2-Me-4-OEt	B86		1-483	Me	Me	2-Me-4-OMe	B85
1-484	Me	Me	2-Me-4-OEt	B86		1-485	Me	Me	2-Me-4-OPr(i)	B87
1-486	Me	Me	3-Cl-4-Br	B88		1-485	Me	Me	2-Me-4-OPr(i)	B87
1-486	Me	Me	3-Cl-4-Br	B88		1-487	Me	Me	3-Br-4-Cl	B89
1-488	Me	Me	3-F-4-Cl	B90		1-487	Me	Me	3-Br-4-Cl	B89
1-488	Me	Me	3-F-4-Cl	B90		1-489	Me	Me	3-Me-4-Br	B91
1-490	Me	Me	3-Cl-4-Cl	B92		1-489	Me	Me	3-Me-4-Br	B91
1-490	Me	Me	3-Cl-4-Cl	B92		1-491	Me	Me	3-Me-4-Cl	B93
1-492	Me	Me	2-Me-4-OMe	B94		1-491	Me	Me	3-Me-4-Cl	B93
1-492	Me	Me	2-Me-4-OMe	B94		1-493	Me	Me	2-Me-4-OEt	B95
1-494	Me	Me	2-Me-4-OPr(i)	B96		1-493	Me	Me	2-Me-4-OEt	B95
1-494	Me	Me	2-Me-4-OPr(i)	B96		1-495	Me	Me	3-Cl-4-Br	B97
1-496	Me	Me	3-Br-4-Cl	B98		1-495	Me	Me	3-Cl-4-Br	B97
1-496	Me	Me	3-Br-4-Cl	B98		1-497	Me	Me	3-F-4-Cl	B99
1-498	Me	Me	3-Me-4-Br	B100		1-497	Me	Me	3-F-4-Cl	B99
1-498	Me	Me	3-Me-4-Br	B100		1-499	Me	Me	3-Cl-4-Cl	B101
1-500	Me	Me	3-Me-4-Cl	B102		1-499	Me	Me	3-Cl-4-Cl	B101
1-500	Me	Me	3-Me-4-Cl	B102		1-501	Me	Me	2-Me-4-OMe	B103
1-502	Me	Me	2-Me-4-OEt	B104		1-501	Me	Me	2-Me-4-OMe	B103
1-502	Me	Me	2-Me-4-OEt	B104		1-503	Me	Me	2-Me-4-OPr(i)	B105
1-504	Me	Me	3-Cl-4-Br	B106		1-503	Me	Me	2-Me-4-OPr(i)	B105
1-504	Me	Me	3-Cl-4-Br	B106		1-505	Me	Me	3-Br-4-Cl	B107
1-506	Me	Me	3-F-4-Cl	B108		1-505	Me	Me	3-Br-4-Cl	B107
1-506	Me	Me	3-F-4-Cl	B108		1-507	Me	Me	3-Me-4-Br	B109
1-508	Me	Me	3-Cl-4-Cl	B110		1-507	Me	Me	3-Me-4-Br	B109
1-508	Me	Me	3-Cl-4-Cl	B110		1-509	Me	Me	3-Me-4-Cl	B111
1-510	Me	Me	2-Me-4-OMe	B112		1-509	Me	Me	3-Me-4-Cl	B111
1-510	Me	Me	2-Me-4-OMe	B112		1-511	Me	Me	2-Me-4-OEt	B113
1-512	Me	Me	2-Me-4-OPr(i)	B114		1-511	Me	Me	2-Me-4-OEt	B113
1-512	Me	Me	2-Me-4-OPr(i)	B114		1-513	Me	Me	3-Cl-4-Br	B115
1-514	Me	Me	3-Br-4-Cl	B116		1-513	Me	Me	3-Cl-4-Br	B115
1-514	Me	Me	3-Br-4-Cl	B116		1-515	Me	Me	3-F-4-Cl	B117
1-516	Me	Me	2-Br-5-OMe	B21	Oil	1-515	Me	Me	3-F-4-Cl	B117
1-516	Me	Me	2-Br-5-OMe	B21	Oil	1-517	Me	Me	2-Me-4-OCH(Me)OMe	B16

Table 1 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	1-518	Me	Me	4-CH ₂Br	B25	Viscosity
1-519	Me	Me	4-CH ₂Br	B62	108-111	1-518	Me	Me	4-CH ₂Br	B25	Viscosity
1-519	Me	Me	4-CH ₂Br	B62	108-111	1-520	Me	Me	4-CH ₂OMe	B25	97-102
1-521	Me	Me	4-CH ₂NMe ₂	B25	Viscosity	1-520	Me	Me	4-CH ₂OMe	B25	97-102
1-521	Me	Me	4-CH ₂NMe ₂	B25	Viscosity	1-522	Me	Me	2-Me-4-OCH ₂Ph	B14
1-523	Me	CH ₂Cl	3-F-4-Cl	B1		1-522	Me	Me	2-Me-4-OCH ₂Ph	B14
1-523	Me	CH ₂Cl	3-F-4-Cl	B1		1-524	Me	CH ₂Cl	3-Me-4-Br	B14
1-525	Me	CH ₂Cl	3-Cl-4-Cl	B16		1-524	Me	CH ₂Cl	3-Me-4-Br	B14
1-525	Me	CH ₂Cl	3-Cl-4-Cl	B16		1-526	Me	CH＝CH ₂	3-Me-4-Cl	B21
1-527	Me	CH＝CH ₂	2-Me-4-OMe	B1		1-526	Me	CH＝CH ₂	3-Me-4-Cl	B21
1-527	Me	CH＝CH ₂	2-Me-4-OMe	B1		1-528	Me	CH＝CH ₂	2-Me-4-OEt	B14
1-529	Me	C≡CH	2-Me-4-OPr(i)	B16		1-528	Me	CH＝CH ₂	2-Me-4-OEt	B14
1-529	Me	C≡CH	2-Me-4-OPr(i)	B16		1-530	Me	C≡CH	3-Cl-4-Br	B21
1-531	Me	C≡CH	3-Br-4-Cl	B1		1-530	Me	C≡CH	3-Cl-4-Br	B21
1-531	Me	C≡CH	3-Br-4-Cl	B1		1-532	Me	CH ₂OMe	3-F-4-Cl	B14
1-533	Me	CH ₂OMe	3-Me-4-Br	B16		1-532	Me	CH ₂OMe	3-F-4-Cl	B14
1-533	Me	CH ₂OMe	3-Me-4-Br	B16		1-534	Me	CH ₂OMe	3-Cl-4-Cl	B21
1-535	Me	Me	3-OMe-4-OMe	B21	138-140	1-534	Me	CH ₂OMe	3-Cl-4-Cl	B21
1-535	Me	Me	3-OMe-4-OMe	B21	138-140	1-536	Me	Me	2-Br	B21	Viscosity
1-537	Me	Me	4-SPh	B1		1-536	Me	Me	2-Br	B21	Viscosity
1-537	Me	Me	4-SPh	B1		1-538	Me	Me	4-CH ₂OMe	B62	74-76
1-539	Me	Me	4-CH ₂NMe ₂	B62	Viscosity	1-538	Me	Me	4-CH ₂OMe	B62	74-76
1-539	Me	Me	4-CH ₂NMe ₂	B62	Viscosity	1-540	Me	Me	4-CH ₂OMe	B21	117-119
1-541	Me	Me	4-CH ₂SMe	B21		1-540	Me	Me	4-CH ₂OMe	B21	117-119
1-541	Me	Me	4-CH ₂SMe	B21		1-542	Me	Me	4-CH ₂NMe ₂	B21
1-543	Me	Me	2-Me-4-Ph(4-Cl)	B21		1-542	Me	Me	4-CH ₂NMe ₂	B21
1-543	Me	Me	2-Me-4-Ph(4-Cl)	B21		1-544	Me	Me	2-Me-4-Ph(4-OMe)	B21
1-545	Me	Me	2-Me-4-CH＝CHCMe ₃	B16		1-544	Me	Me	2-Me-4-Ph(4-OMe)	B21
1-545	Me	Me	2-Me-4-CH＝CHCMe ₃	B16		1-546	Me	Me	2-Me-4-Ph(4-CF ₃)	B21
1-547	Me	Me	2-Me-4-CH＝CHPh	B14		1-546	Me	Me	2-Me-4-Ph(4-CF ₃)	B21
1-547	Me	Me	2-Me-4-CH＝CHPh	B14		1-548	Me	Me	2-Me-4-CH ₂SO ₂Me	B21
1-549	Me	Me	4-Me	B25	96-98	1-548	Me	Me	2-Me-4-CH ₂SO ₂Me	B21
1-549	Me	Me	4-Me	B25	96-98	1-550	Me	Me	4-Me	B62	98-102
1-551	Me	Me	4-SCO ₂Me	B1		1-550	Me	Me	4-Me	B62	98-102
1-551	Me	Me	4-SCO ₂Me	B1		1-552	Me	Me	2-Me-4-CH ₂CN	B16
1-553	Me	Me	4-NHPh	B1		1-552	Me	Me	2-Me-4-CH ₂CN	B16
1-553	Me	Me	4-NHPh	B1		1-554	Me	Me	2-Me-4-OBu(t)	B21

Table 2

Table 2 (continuing)

No.	R ¹	R ²	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	X	B	Physical properties (mp ℃)	2-31	Me	Me	H	B48
2-32	Me	Me	H	B49		2-31	Me	Me	H	B48
2-32	Me	Me	H	B49		2-33	Me	Me	H	B19
2-34	Me	Me	H	B20		2-33	Me	Me	H	B19
2-34	Me	Me	H	B20		2-35	Me	Me	H	B50
2-36	Me	Me	1-Me	B21		2-35	Me	Me	H	B50
2-36	Me	Me	1-Me	B21		2-37	Me	Me	1-Me	B16

Table 3

Table 4

No.	R ¹	R ²	X ¹	X ²	X ³	B	Physical properties (mp ℃)
No.	R ¹	R ²	X ¹	X ²	X ³	B	Physical properties (mp ℃)	4-1	Me	Me	H	H	H	B1
4-2	Me	Me	H	H	H	B5		4-1	Me	Me	H	H	H	B1
4-2	Me	Me	H	H	H	B5		4-3	Me	Me	H	H	H	B8
4-4	Me	Me	H	H	H	B16		4-3	Me	Me	H	H	H	B8
4-4	Me	Me	H	H	H	B16		4-5	Me	Me	H	H	H	B21
4-6	Me	Me	H	F	F	B1		4-5	Me	Me	H	H	H	B21
4-6	Me	Me	H	F	F	B1		4-7	Me	Me	H	F	F	B5
4-8	Me	Me	H	F	F	B8		4-7	Me	Me	H	F	F	B5
4-8	Me	Me	H	F	F	B8		4-9	Me	Me	H	F	F	B11
4-10	Me	Me	H	F	F	B21	120-122	4-9	Me	Me	H	F	F	B11
4-10	Me	Me	H	F	F	B21	120-122	4-11	Me	Me	Me	H	H	B1
4-12	Me	Me	Me	H	H	B4		4-11	Me	Me	Me	H	H	B1
4-12	Me	Me	Me	H	H	B4		4-13	Me	Me	Me	H	H	B8
4-14	Me	Me	Me	H	H	B16		4-13	Me	Me	Me	H	H	B8
4-14	Me	Me	Me	H	H	B16		4-15	Me	Me	Me	H	H	B21
4-16	Me	Me	Me	F	F	B1		4-15	Me	Me	Me	H	H	B21
4-16	Me	Me	Me	F	F	B1		4-17	Me	Me	Me	F	F	B15
4-18	Me	Me	Me	F	F	B10		4-17	Me	Me	Me	F	F	B15
4-18	Me	Me	Me	F	F	B10		4-19	Me	Me	Me	F	F	B21	74-78
4-20	Me	Me	Me	F	F	B25		4-19	Me	Me	Me	F	F	B21	74-78
4-20	Me	Me	Me	F	F	B25		4-21	Me	Me	Me	H	Me	B21
4-22	Me	Me	Me	H	Me	B16		4-21	Me	Me	Me	H	Me	B21
4-22	Me	Me	Me	H	Me	B16		4-23	Me	Me	Me	H	Me	B14
4-24	Me	Me	Me	Me	H	B1		4-23	Me	Me	Me	H	Me	B14
4-24	Me	Me	Me	Me	H	B1		4-25	Me	Me	Me	Me	H	B5
4-26	Me	Me	Me	Me	H	B8		4-25	Me	Me	Me	Me	H	B5
4-26	Me	Me	Me	Me	H	B8		4-27	Me	Me	Me	H	Me	B1
4-28	Me	Me	Me	H	Me	B5		4-27	Me	Me	Me	H	Me	B1
4-28	Me	Me	Me	H	Me	B5		4-29	Me	Me	Me	H	Me	B8
4-30	Me	Me	Me	H	Me	B71		4-29	Me	Me	Me	H	Me	B8

Table 5

No.	R ¹	R ²	X ¹	X ²	X ³	B	Physical properties (mp ℃)
No.	R ¹	R ²	X ¹	X ²	X ³	B	Physical properties (mp ℃)	5-1	Me	Me	H	H	H	B1
5-2	Me	Me	H	H	H	B5		5-1	Me	Me	H	H	H	B1
5-2	Me	Me	H	H	H	B5		5-3	Me	Me	H	H	H	B7
5-4	Me	Me	H	H	H	B14		5-3	Me	Me	H	H	H	B7
5-4	Me	Me	H	H	H	B14		5-5	Me	Me	H	H	H	B15
5-6	Me	Me	Me	H	H	B1		5-5	Me	Me	H	H	H	B15
5-6	Me	Me	Me	H	H	B1		5-7	Me	Me	Me	H	H	B5
5-8	Me	Me	Me	H	H	B8		5-7	Me	Me	Me	H	H	B5
5-8	Me	Me	Me	H	H	B8		5-9	Me	Me	Me	H	H	B11
5-10	Me	Me	Me	H	H	B21		5-9	Me	Me	Me	H	H	B11
5-10	Me	Me	Me	H	H	B21		5-11	Me	Me	H	F	F	B1
5-12	Me	Me	H	F	F	B4		5-11	Me	Me	H	F	F	B1
5-12	Me	Me	H	F	F	B4		5-13	Me	Me	H	F	F	B8
5-14	Me	Me	H	F	F	B16		5-13	Me	Me	H	F	F	B8
5-14	Me	Me	H	F	F	B16		5-15	Me	Me	H	F	F	B21
5-16	Me	Me	Me	F	F	B1		5-15	Me	Me	H	F	F	B21
5-16	Me	Me	Me	F	F	B1		5-17	Me	Me	Me	F	F	B15
5-18	Me	Me	Me	F	F	B10		5-17	Me	Me	Me	F	F	B15
5-18	Me	Me	Me	F	F	B10		5-19	Me	Me	Me	F	F	B21
5-20	Me	Me	Me	F	F	B25		5-19	Me	Me	Me	F	F	B21
5-20	Me	Me	Me	F	F	B25		5-21	Me	Me	Me	H	Me	B21
5-22	Me	Me	Me	H	Me	B16		5-21	Me	Me	Me	H	Me	B21
5-22	Me	Me	Me	H	Me	B16		5-23	Me	Me	Me	H	Me	B14
5-24	Me	Me	Me	F	H	B1		5-23	Me	Me	Me	H	Me	B14
5-24	Me	Me	Me	F	H	B1		5-25	Me	Me	Me	F	H	B5
5-26	Me	Me	Me	F	H	B8		5-25	Me	Me	Me	F	H	B5
5-26	Me	Me	Me	F	H	B8		5-27	Me	Me	Me	Me	H	B14
5-28	Me	Me	Me	Me	H	B16		5-27	Me	Me	Me	Me	H	B14
5-28	Me	Me	Me	Me	H	B16		5-29	Me	Me	Me	Me	H	B21
5-30	Me	Me	Me	Me	Me	B21		5-29	Me	Me	Me	Me	H	B21

Table 6

No.	R ¹	R ²	R ³	X	B	Physical properties (mp ℃)
No.	R ¹	R ²	R ³	X	B	Physical properties (mp ℃)	6-1	Me	Me	CO ₂Bu(t)	4-Br	B21	Oil
6-2	Me	Me	COMe	4-Br	B21	Oil	6-1	Me	Me	CO ₂Bu(t)	4-Br	B21	Oil
6-2	Me	Me	COMe	4-Br	B21	Oil	6-3	Me	Me	COMe	3-Cl-4-Cl	B21	Oil
6-4	Me	Me	Me	3-Cl-4-Cl	B1	147-150	6-3	Me	Me	COMe	3-Cl-4-Cl	B21	Oil
6-4	Me	Me	Me	3-Cl-4-Cl	B1	147-150	6-5	Me	Me	CO ₂Bu(t)	3-Cl-4-Cl	B21	66-68
6-6	Me	Me	SCCl ₃	3-Br-4-Cl	B1		6-5	Me	Me	CO ₂Bu(t)	3-Cl-4-Cl	B21	66-68
6-6	Me	Me	SCCl ₃	3-Br-4-Cl	B1		6-7	Me	Me	SPh	3-Cl-4-Br	B5
6-8	Me	Me	SOPh	3-Me-4-Br	B8		6-7	Me	Me	SPh	3-Cl-4-Br	B5
6-8	Me	Me	SOPh	3-Me-4-Br	B8		6-9	Me	Me	SO ₂Ph	3-Me-4-Cl	B14
6-10	Me	Me	SO ₂Me	3-Cl-4-Cl	B16		6-9	Me	Me	SO ₂Ph	3-Me-4-Cl	B14
6-10	Me	Me	SO ₂Me	3-Cl-4-Cl	B16		6-11	Me	Me	SO ₂CF ₃	3-F-4-Cl	B21
6-12	Me	Me	SO ₂NMe ₂	2-Me-4-OMe	B71		6-11	Me	Me	SO ₂CF ₃	3-F-4-Cl	B21
6-12	Me	Me	SO ₂NMe ₂	2-Me-4-OMe	B71		6-13	Me	Me	CH ₂OMe	2-Me-4-OEt	B1
6-14	Me	Me	CH ₂SMe	2-Me-4-OPr(i)	B5		6-13	Me	Me	CH ₂OMe	2-Me-4-OEt	B1
6-14	Me	Me	CH ₂SMe	2-Me-4-OPr(i)	B5		6-15	Me	Me	CN	3-Br-4-Br	B8
6-16	Me	Me	CHO	2-Me-4-Cl	B14		6-15	Me	Me	CN	3-Br-4-Br	B8
6-16	Me	Me	CHO	2-Me-4-Cl	B14		6-17	Me	Me	CH ₂CF ₃	2-Me-4-Br	B16
6-18	Me	Me	OCH ₂CF ₃	3-Br-4-Cl	B21		6-17	Me	Me	CH ₂CF ₃	2-Me-4-Br	B16
6-18	Me	Me	OCH ₂CF ₃	3-Br-4-Cl	B21		6-19	Me	Me	D3	3-Cl-4-Br	B71
6-20	Me	Me	OH	3-Me-4-Br	B1		6-19	Me	Me	D3	3-Cl-4-Br	B71
6-20	Me	Me	OH	3-Me-4-Br	B1		6-21	Me	Me	CO ₂CH ₂Ph	3-Me-4-Cl	B5
6-22	Me	Me	CO ₂CH ₂OMe	3-Cl-4-Cl	B8		6-21	Me	Me	CO ₂CH ₂Ph	3-Me-4-Cl	B5
6-22	Me	Me	CO ₂CH ₂OMe	3-Cl-4-Cl	B8		6-23	Me	Me	COPh	3-Cl-4-Cl	B14
6-24	Me	Me	COCF ₃	3-Cl-4-Cl	B16		6-23	Me	Me	COPh	3-Cl-4-Cl	B14
6-24	Me	Me	COCF ₃	3-Cl-4-Cl	B16		6-25	Me	Me	CH ₂C≡CH	3-Cl-4-Cl	B21
6-26	Me	Me	CH ₂CH＝CH ₂	3-F-4-Cl	B71		6-25	Me	Me	CH ₂C≡CH	3-Cl-4-Cl	B21
6-26	Me	Me	CH ₂CH＝CH ₂	3-F-4-Cl	B71		6-27	Me	Me	CH ₂CN	2-Me-4-OMe	B1
6-28	Me	Me	Cyclopentyloxy	2-Me-4-OEt	B5		6-27	Me	Me	CH ₂CN	2-Me-4-OMe	B1
6-28	Me	Me	Cyclopentyloxy	2-Me-4-OEt	B5		6-29	Me	Me	CH ₂CH ₂OCHF ₂	2-Me-4-OPr(i)	B8
6-30	Me	Me	CH ₂CH ₂NH ₂	3-Br-4-Br	B14		6-29	Me	Me	CH ₂CH ₂OCHF ₂	2-Me-4-OPr(i)	B8
6-30	Me	Me	CH ₂CH ₂NH ₂	3-Br-4-Br	B14		6-31	Me	Me	CH ₂CH ₂NHMe	2-Me-4-Cl	B16
6-32	Me	Me	CH ₂CH ₂NMe ₂	2-Me-4-Br	B21		6-31	Me	Me	CH ₂CH ₂NHMe	2-Me-4-Cl	B16

Table 7

No.	A	W ¹	R ¹	R ²	W ²	B	Physical properties (mp ℃)
No.	A	W ¹	R ¹	R ²	W ²	B	Physical properties (mp ℃)	7-1	The 2-thienyl	O	Me	Me	O	B1	101-105
7-2	The 2-thienyl	O	Me	Me	O	B21	118-121	7-1	The 2-thienyl	O	Me	Me	O	B1	101-105
7-2	The 2-thienyl	O	Me	Me	O	B21	118-121	7-3	The 3-thienyl	O	Me	Me	O	B1	121-125
7-4	The 5-Cl-3-thienyl	O	Me	Me	O	B21	138-142	7-3	The 3-thienyl	O	Me	Me	O	B1	121-125
7-4	The 5-Cl-3-thienyl	O	Me	Me	O	B21	138-142	7-5	The 2-Cl-5-Cl-3-thienyl	O	Me	Me	O	B21	119-121
7-6	The 5-Cl-2-thienyl	O	Me	Me	O	B21	127-132	7-5	The 2-Cl-5-Cl-3-thienyl	O	Me	Me	O	B21	119-121
7-6	The 5-Cl-2-thienyl	O	Me	Me	O	B21	127-132	7-7	The 5-Cl-2-thienyl	O	Me	Me	O	B1	115-120
7-8	The 4-Cl-2-thienyl	O	Me	Me	O	B21	119-121	7-7	The 5-Cl-2-thienyl	O	Me	Me	O	B1	115-120
7-8	The 4-Cl-2-thienyl	O	Me	Me	O	B21	119-121	7-9	The 4-Cl-2-thienyl	O	Me	Me	O	B1	Oil
7-10	The 1-naphthyl	O	Me	Me	O	B48		7-9	The 4-Cl-2-thienyl	O	Me	Me	O	B1	Oil
7-10	The 1-naphthyl	O	Me	Me	O	B48		7-11	The 1-naphthyl	O	Me	Me	O	B49
7-12	The 1-naphthyl	O	Me	Me	O	B19		7-11	The 1-naphthyl	O	Me	Me	O	B49
7-12	The 1-naphthyl	O	Me	Me	O	B19		7-13	The 1-naphthyl	O	Me	Me	O	B20
7-14	The 1-naphthyl	O	Me	Me	O	B50		7-13	The 1-naphthyl	O	Me	Me	O	B20
7-14	The 1-naphthyl	O	Me	Me	O	B50		7-15	The 1-naphthyl	O	Me	Me	O	B12
7-16	The 1-naphthyl	O	Me	Me	O	B13		7-15	The 1-naphthyl	O	Me	Me	O	B12
7-16	The 1-naphthyl	O	Me	Me	O	B13		7-17	The 2-thienyl	O	Me	Me	O	B48
7-18	The 2-thienyl	O	Me	Me	O	B49		7-17	The 2-thienyl	O	Me	Me	O	B48
7-18	The 2-thienyl	O	Me	Me	O	B49		7-19	The 2-thienyl	O	Me	Me	O	B19
7-20	The 2-thienyl	O	Me	Me	O	B20		7-19	The 2-thienyl	O	Me	Me	O	B19
7-20	The 2-thienyl	O	Me	Me	O	B20		7-21	The 2-thienyl	O	Me	Me	O	B50
7-22	The 2-thienyl	O	Me	Me	O	B12		7-21	The 2-thienyl	O	Me	Me	O	B50
7-22	The 2-thienyl	O	Me	Me	O	B12		7-23	The 2-thienyl	O	Me	Me	O	B13
7-24	The 3-thienyl	O	Me	Me	O	B48		7-23	The 2-thienyl	O	Me	Me	O	B13
7-24	The 3-thienyl	O	Me	Me	O	B48		7-25	The 3-thienyl	O	Me	Me	O	B49
7-26	The 3-thienyl	O	Me	Me	O	B19		7-25	The 3-thienyl	O	Me	Me	O	B49
7-26	The 3-thienyl	O	Me	Me	O	B19		7-27	The 3-thienyl	O	Me	Me	O	B20
7-28	The 3-thienyl	O	Me	Me	O	B50		7-27	The 3-thienyl	O	Me	Me	O	B20
7-28	The 3-thienyl	O	Me	Me	O	B50		7-29	The 3-thienyl	O	Me	Me	O	B12
7-30	The 3-thienyl	O	Me	Me	O	B13		7-29	The 3-thienyl	O	Me	Me	O	B12

Table 7 (continuing)

No.	A	W ¹	R ¹	R ²	W ²	B	Physical properties (mp ℃)
No.	A	W ¹	R ¹	R ²	W ²	B	Physical properties (mp ℃)	7-31	The 2-pyridyl	O	Me	Me	O	B48
7-32	The 2-pyridyl	O	Me	Me	O	B49		7-31	The 2-pyridyl	O	Me	Me	O	B48
7-32	The 2-pyridyl	O	Me	Me	O	B49		7-33	The 2-pyridyl	O	Me	Me	O	B19
7-34	The 2-pyridyl	O	Me	Me	O	B20		7-33	The 2-pyridyl	O	Me	Me	O	B19
7-34	The 2-pyridyl	O	Me	Me	O	B20		7-35	The 2-pyridyl	O	Me	Me	O	B50
7-36	The 2-pyridyl	O	Me	Me	O	B12		7-35	The 2-pyridyl	O	Me	Me	O	B50
7-36	The 2-pyridyl	O	Me	Me	O	B12		7-37	The 2-pyridyl	O	Me	Me	O	B13
7-38	The 3-pyridyl	O	Me	Me	O	B48		7-37	The 2-pyridyl	O	Me	Me	O	B13
7-38	The 3-pyridyl	O	Me	Me	O	B48		7-39	The 3-pyridyl	O	Me	Me	O	B49
7-40	The 3-pyridyl	O	Me	Me	O	B19		7-39	The 3-pyridyl	O	Me	Me	O	B49
7-40	The 3-pyridyl	O	Me	Me	O	B19		7-41	The 3-pyridyl	O	Me	Me	O	B20
7-42	The 3-pyridyl	O	Me	Me	O	B50		7-41	The 3-pyridyl	O	Me	Me	O	B20
7-42	The 3-pyridyl	O	Me	Me	O	B50		7-43	The 3-pyridyl	O	Me	Me	O	B12
7-44	The 4-pyridyl	O	Me	Me	O	B13		7-43	The 3-pyridyl	O	Me	Me	O	B12
7-44	The 4-pyridyl	O	Me	Me	O	B13		7-45	The 4-pyridyl	O	Me	Me	O	B48
7-46	The 4-pyridyl	O	Me	Me	O	B49		7-45	The 4-pyridyl	O	Me	Me	O	B48
7-46	The 4-pyridyl	O	Me	Me	O	B49		7-47	The 4-pyridyl	O	Me	Me	O	B19
7-48	The 4-pyridyl	O	Me	Me	O	B20		7-47	The 4-pyridyl	O	Me	Me	O	B19
7-48	The 4-pyridyl	O	Me	Me	O	B20		7-49	The 4-pyridyl	O	Me	Me	O	B50
7-50	The 4-pyridyl	O	Me	Me	O	B12		7-49	The 4-pyridyl	O	Me	Me	O	B50
7-50	The 4-pyridyl	O	Me	Me	O	B12		7-51	The 4-pyridyl	O	Me	Me	O	B13
7-52	Indol-3-yl	O	Me	Me	O	B48		7-51	The 4-pyridyl	O	Me	Me	O	B13
7-52	Indol-3-yl	O	Me	Me	O	B48		7-53	Indol-3-yl	O	Me	Me	O	B49
7-54	Indol-3-yl	O	Me	Me	O	B19		7-53	Indol-3-yl	O	Me	Me	O	B49
7-54	Indol-3-yl	O	Me	Me	O	B19		7-55	Indol-3-yl	O	Me	Me	O	B20
7-56	Indol-3-yl	O	Me	Me	O	B50		7-55	Indol-3-yl	O	Me	Me	O	B20
7-56	Indol-3-yl	O	Me	Me	O	B50		7-57	Indol-3-yl	O	Me	Me	O	B12
7-58	Indol-3-yl	O	Me	Me	O	B13		7-57	Indol-3-yl	O	Me	Me	O	B12
7-58	Indol-3-yl	O	Me	Me	O	B13		7-59	The N-Me-indol-3-yl	O	Me	Me	O	B48
7-60	The N-Me-indol-3-yl	O	Me	Me	O	B49		7-59	The N-Me-indol-3-yl	O	Me	Me	O	B48

Table 7 (continuing)

No.	A	W ¹	R ¹	R ²	W ²	B	Physical properties (mp ℃)
No.	A	W ¹	R ¹	R ²	W ²	B	Physical properties (mp ℃)	7-61	The N-Me-indol-3-yl	O	Me	Me	O	B19
7-62	The N-Me-indol-3-yl	O	Me	Me	O	B20		7-61	The N-Me-indol-3-yl	O	Me	Me	O	B19
7-62	The N-Me-indol-3-yl	O	Me	Me	O	B20		7-63	The N-Me-indol-3-yl	O	Me	Me	O	B50
7-64	The N-Me-indol-3-yl	O	Me	Me	O	B12		7-63	The N-Me-indol-3-yl	O	Me	Me	O	B50
7-64	The N-Me-indol-3-yl	O	Me	Me	O	B12		7-65	The N-Me-indol-3-yl	O	Me	Me	O	B13
7-66	The 3-thienyl	O	Me	Me	O	B21	131-133	7-65	The N-Me-indol-3-yl	O	Me	Me	O	B13
7-66	The 3-thienyl	O	Me	Me	O	B21	131-133	7-67	Ph(3，4-Cl ₂)	S	Me	Me	O	B21
7-68	Ph(3，4-Cl ₂)	O	Me	Me	S	B21		7-67	Ph(3，4-Cl ₂)	S	Me	Me	O	B21
7-68	Ph(3，4-Cl ₂)	O	Me	Me	S	B21		7-69	The 2-Cl-5-pyridyl	O	Me	Me	O	B21
7-70	The 3-pyridyl	O	Me	Me	O	B21		7-69	The 2-Cl-5-pyridyl	O	Me	Me	O	B21
7-70	The 3-pyridyl	O	Me	Me	O	B21		7-71	The 2-OMe-5-pyridyl	O	Me	Me	O	B21
7-72	The 2-Cl-5-pyridyl	O	Me	Me	O	B16		7-71	The 2-OMe-5-pyridyl	O	Me	Me	O	B21
7-72	The 2-Cl-5-pyridyl	O	Me	Me	O	B16		7-73	The 2-OMe-5-pyridyl	O	Me	Me	O	B16
7-74	The 5-OMe-2-pyridyl	O	Me	Me	O	B21		7-73	The 2-OMe-5-pyridyl	O	Me	Me	O	B16
7-74	The 5-OMe-2-pyridyl	O	Me	Me	O	B21		7-75	The 5-OMe-2-pyridyl	O	Me	Me	O	B16
7-76	The 5-Cl-2-pyridyl	O	Me	Me	O	B21		7-75	The 5-OMe-2-pyridyl	O	Me	Me	O	B16
7-76	The 5-Cl-2-pyridyl	O	Me	Me	O	B21		7-77	The 5-Cl-2-pyridyl	O	Me	Me	O	B16

Table 8

No.	R ¹	R ²	X ¹	X ²	X ³	X ⁴	B	Physical properties (mp ℃)
No.	R ¹	R ²	X ¹	X ²	X ³	X ⁴	B	Physical properties (mp ℃)	8-1	Me	Me	Me	F	F	H	B1
8-2	Me	Me	Me	F	F	H	B5		8-1	Me	Me	Me	F	F	H	B1
8-2	Me	Me	Me	F	F	H	B5		8-3	Me	Me	Me	F	F	H	B8
8-4	Me	Me	Me	F	F	H	B14		8-3	Me	Me	Me	F	F	H	B8
8-4	Me	Me	Me	F	F	H	B14		8-5	Me	Me	Me	F	F	H	B16
8-6	Me	Me	Me	F	F	H	B21		8-5	Me	Me	Me	F	F	H	B16
8-6	Me	Me	Me	F	F	H	B21		8-7	Me	Me	Me	F	F	H	B71
8-8	Me	Me	Me	H	H	H	B1		8-7	Me	Me	Me	F	F	H	B71
8-8	Me	Me	Me	H	H	H	B1		8-9	Me	Me	Me	H	H	H	B14
8-10	Me	Me	Me	H	H	H	B16		8-9	Me	Me	Me	H	H	H	B14
8-10	Me	Me	Me	H	H	H	B16		8-11	Me	Me	Me	Me	H	H	B1
8-12	Me	Me	Me	Me	H	H	B5		8-11	Me	Me	Me	Me	H	H	B1
8-12	Me	Me	Me	Me	H	H	B5		8-13	Me	Me	Me	Me	H	H	B8
8-14	Me	Me	Me	Me	H	H	B14		8-13	Me	Me	Me	Me	H	H	B8
8-14	Me	Me	Me	Me	H	H	B14		8-15	Me	Me	Me	Me	H	H	B16
8-16	Me	Me	Me	Me	H	H	B21		8-15	Me	Me	Me	Me	H	H	B16
8-16	Me	Me	Me	Me	H	H	B21		8-17	Me	Me	Me	Me	H	H	B71
8-18	Me	Me	Me	Me	Me	H	B1		8-17	Me	Me	Me	Me	H	H	B71
8-18	Me	Me	Me	Me	Me	H	B1		8-19	Me	Me	Me	Me	Me	H	B5
8-20	Me	Me	Me	Me	Me	H	B8		8-19	Me	Me	Me	Me	Me	H	B5
8-20	Me	Me	Me	Me	Me	H	B8		8-21	Me	Me	Me	Me	Me	H	B14
8-22	Me	Me	Me	Me	Me	H	B16		8-21	Me	Me	Me	Me	Me	H	B14
8-22	Me	Me	Me	Me	Me	H	B16		8-23	Me	Me	Me	Me	Me	H	B21
8-24	Me	Me	Me	Me	Me	H	B71		8-23	Me	Me	Me	Me	Me	H	B21
8-24	Me	Me	Me	Me	Me	H	B71		8-25	Me	Me	H	F	F	H	B5
8-26	Me	Me	H	F	F	H	B8		8-25	Me	Me	H	F	F	H	B5
8-26	Me	Me	H	F	F	H	B8		8-27	Me	Me	Me	F	F	Me	B14
8-28	Me	Me	Me	F	F	Me	B16		8-27	Me	Me	Me	F	F	Me	B14
8-28	Me	Me	Me	F	F	Me	B16		8-29	Me	Me	Me	Me	H	Me	B21
8-30	Me	Me	Me	Me	Me	Me	B71		8-29	Me	Me	Me	Me	H	Me	B21

Table 9

No.	R ¹	R ²	X ¹	X ²	X ³	X ⁴	B	Physical properties (mp ℃)
No.	R ¹	R ²	X ¹	X ²	X ³	X ⁴	B	Physical properties (mp ℃)	9-1	Me	Me	Me	F	F	H	B1
9-2	Me	Me	Me	F	F	H	B5		9-1	Me	Me	Me	F	F	H	B1
9-2	Me	Me	Me	F	F	H	B5		9-3	Me	Me	Me	F	F	H	B8
9-4	Me	Me	Me	F	F	H	B14		9-3	Me	Me	Me	F	F	H	B8
9-4	Me	Me	Me	F	F	H	B14		9-5	Me	Me	Me	F	F	H	B16
9-6	Me	Me	Me	F	F	H	B21		9-5	Me	Me	Me	F	F	H	B16
9-6	Me	Me	Me	F	F	H	B21		9-7	Me	Me	Me	F	F	H	B71
9-8	Me	Me	Me	H	H	H	B1		9-7	Me	Me	Me	F	F	H	B71
9-8	Me	Me	Me	H	H	H	B1		9-9	Me	Me	Me	H	H	H	B14
9-10	Me	Me	Me	H	H	H	B16		9-9	Me	Me	Me	H	H	H	B14
9-10	Me	Me	Me	H	H	H	B16		9-11	Me	Me	Me	Me	H	H	B1
9-12	Me	Me	Me	Me	H	H	B5		9-11	Me	Me	Me	Me	H	H	B1
9-12	Me	Me	Me	Me	H	H	B5		9-13	Me	Me	Me	Me	H	H	B8
9-14	Me	Me	Me	Me	H	H	B14		9-13	Me	Me	Me	Me	H	H	B8
9-14	Me	Me	Me	Me	H	H	B14		9-15	Me	Me	Me	Me	H	H	B16
9-16	Me	Me	Me	Me	H	H	B21		9-15	Me	Me	Me	Me	H	H	B16
9-16	Me	Me	Me	Me	H	H	B21		9-17	Me	Me	Me	Me	H	H	B71
9-18	Me	Me	Me	Me	Me	H	B1		9-17	Me	Me	Me	Me	H	H	B71
9-18	Me	Me	Me	Me	Me	H	B1		9-19	Me	Me	Me	Me	Me	H	B5
9-20	Me	Me	Me	Me	Me	H	B8		9-19	Me	Me	Me	Me	Me	H	B5
9-20	Me	Me	Me	Me	Me	H	B8		9-21	Me	Me	Me	Me	Me	H	B14
9-22	Me	Me	Me	Me	Me	H	B16		9-21	Me	Me	Me	Me	Me	H	B14
9-22	Me	Me	Me	Me	Me	H	B16		9-23	Me	Me	Me	Me	Me	H	B21
9-24	Me	Me	Me	Me	Me	H	B71		9-23	Me	Me	Me	Me	Me	H	B21
9-24	Me	Me	Me	Me	Me	H	B71		9-25	Me	Me	H	F	F	H	B5
9-26	Me	Me	H	F	F	H	B8		9-25	Me	Me	H	F	F	H	B5
9-26	Me	Me	H	F	F	H	B8		9-27	Me	Me	Me	F	F	Me	B14
9-28	Me	Me	Me	F	F	Me	B16		9-27	Me	Me	Me	F	F	Me	B14
9-28	Me	Me	Me	F	F	Me	B16		9-29	Me	Me	Me	Me	H	Me	B21
9-30	Me	Me	Me	Me	Me	Me	B71		9-29	Me	Me	Me	Me	H	Me	B21

Table 10

Table 10 (continuing)

No.	¹H-NMR δ ppm (solvent: CDCl ₃/400MHz)
No.	¹H-NMR δ ppm (solvent: CDCl ₃/400MHz)	1-184	1.73(s，6H)，2.46(s，3H)，3.82(s，3H)，6.84(d，1H)，6.85-6.91(m，3H)， 7.00(t，1H)，7.26(d，1H)，7.27-7.39(m，2H)
1-187	1.75(s，6H)，2.38(s，3H)，2.43(s，3H)，4.35(q，2H)，6.69(s，H)， 6.71(dd，1H)，6.82(d，1H)，6.86(d，1H)，7.25(d，1H)，7.52(d，1H)	1-184
1-187		1-189	1.52(d，3H)，2.57(s，3H)，5.67(m，1H)，6.90(d，1H)，7.0(bd，1H)， 7.31(d，1H)，7.50(d，2H)，7.97(d，2H)
1-231	1.77(s，6H)，2.25(s，3H)，2.48(s，3H)，3.77(s，3H)，6.85(dd，1H)， 6.87(d，1H)，6.89(s，1H)，6.97(d，1H)，7.15(d，1H)，7.26(d，1H)	1-189
1-231		1-270	1.75(s，6H)，2.29(s，3H)，2.36(s，3H)，2.44(s，3H)，6.73(s，1H)， 6.86(d，1H)，6.91(dd，1H)，6.99(d，1H)，7.25(d，1H)，7.51(d，1H)
1-271	1.31(d，9H)，1.73(s，6H)，2.31(s，3H)，2.44(s，3H)，6.75(s，1H)， 6.85(d，2H)，7.17(dd，1H)，7.25(d，1H)，7.28(bs，1H)，7.39(d，1H)	1-270
1-271		1-273	0.96(t，3H)，1.26-1.31(m，3H)，1.61-1.75(m，2H)，2.35(s，3H)， 2.44(s，3H)，4.32(m，1H)，6.64(dd，1H)，6.75(d，1H)，6.85(d，1H)， 6.88(s，1H)，7.24(d，1H)，7.47(d，1H)
1-276	1.75(s，6H)，2.38(s，3H)，2.43(s，3H)，6.71(s，1H)，6.85(d，1H) 7.24(d，1H)，7.32(dd，1H)，7,34-7.36(m，3H)，7.43(bs，1H)， 7.51-7.54(m，2H)	1-273
1-276		1-282	0.24(s，9H)，1.73(s，6H)，2.33(s，3H)，2.44(s，3H)，6.68(s，1H)， 6.86(d，1H)，7.24(dd，1H)，7.25(d，1H)，7.36(bs，1H)，7.42(d，1H)
1-516	1.78(s，6H)，2.53(s，3H)，3.79(s，3H)，6.76(s，1H)，6.83(dd，1H)， 6.89(d，1H)，7.14(d，1H)，7.29(d，1H)，7.47(d，1H)	1-282
1-516		1-518	1.78(s，6H)，4.43(s，2H)，6.96(d，1H)，7.38(d，2H)，7.41(d，1H)， 7.80(s，1H)，7.96(d，2H)
1-521	1.74(s，6H)，2.13(s，6H)，3.34(s，2H)，6.87(d，1H)，7.25(d，2H)， 7.32(d，1H)，7.86(s，1H)，7.88(d，2H)	1-518
1-521		1-536	1.73(s，6H)，2.48(s，3H)，6.75(s，1H)，6.85(d，1H)， 7.22-7.26(m，2H)，7.32(dt，1H)，7.55-7.58(m，2H)
1-539	1.80(s，6H)，2.30(s，6H)，3.56(s，2H)，7.01(d，1H)，7.39(m，3H)， 7.93(s，1H)，7.98(d，2H)	1-536
1-539		2-4	1.87(s，6H)，2.45(s，3H)，3.80(s，3H)，7.54(m，2H)，7.69(s，1H)， 7.90(m，3H)，8.00(d，1H)，8.50(s，1H)
6-1	0.75(s，3H)，1.34(s，9H)，1.59(s，3H)，2.57(s，3H)，6.93(d，1H)， 7.38(d，1H)，7.39(d，2H)7.54(d，2H)，	2-4
6-1		6-2	0.74(s，3H)，1.62(s，3H)，2.04(s，3H)，2.56(s，3H)，6.92(d，1H)， 7.35(d，1H)，7.37(d，2H)，7.53(d，2H)，
6-3	1.60(s，6H)，2.04(s，3H)，2.54(s，3H)，6.91(d，1H)，7.29(m，1H)， 7.36(m，1H)，7.45(d，1H)，7.54(s，1H)	6-2
6-3		7-9	1.60(s，6H)，2.30(s，3H)，3.76(s，3H)，6.67(s，1H)，6.91(d，1H)， 7.25(d，1H)

The experimental example of the present composition will be described below.In each test, control index is to determine on the basis of following standard.

[control index]: [illness outbreak degree: range estimation]

5: do not have discernible lesion or sporulation

4: the number of the area of lesion, the length of lesion, lesion or the area of sporulation are less than untreated geographic 10%

3: the number of the area of lesion, the length of lesion, lesion or the area of sporulation are less than untreated geographic 40%

2: the number of the area of lesion, the length of lesion, lesion or the area of sporulation are less than untreated geographic 70%

1: the number of the area of lesion, the length of lesion, lesion or the area of sporulation are untreated geographic at least 70%

Experimental example 1: to the test of the preventive and therapeutic effect of wheat powdery mildew

Wheat (is cultivated plants: Norin-61-go) cultivate in diameter is the plastic tub of 7.5cm, and reach the 1.5-leafage during stage when it, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.After this chemical solution drying (with using on the same day), sprinkle and inoculate the asexual spore of cereal powdery mildew (Erysiphe graminis), and remain in 20 ℃ the thermostatic chamber.After inoculation 6-7 days, observe the area of sporulation, and determine control index according to above-mentioned judgement criteria.Carry out this test respectively for above-claimed cpd No.1-13,1-29,1-39,1-54,1-90,1-96,1-100,1-101,1-106,1-107,1-109,1-124,1-125,1-127,1-148,1-152,1-156,1-174,1-175,1-190,1-205,1-516,3-4,3-9,3-10,3-12,3-19,3-20,4-19,6-1 and 7-2, all compound exhibits control index under 500ppm concentration is 4 or 5 effect.

Experimental example 2: to the test of the preventive and therapeutic effect of powdery mildew of cucumber

Cucumber (is cultivated plants: Sagamihanpaku) cultivate in diameter is the plastic tub of 7.5cm, and reach the 1.5-leafage during stage when it, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.The conidial suspension of melon powdery mildew (Sphaerothecafuliginea) is sprayed and inoculated to (with using on the same day or second day) after this chemical solution drying, and remain in 20 ℃ the thermostatic chamber.After inoculation 6-7 days, observe the area of sporulation, and determine control index according to above-mentioned judgement criteria.For above-claimed cpd No.1-6,1-9,1-11,1-14,1-15,1-17 to 1-22,1-27 to 1-29,1-32,1-33,1-36,1-39,1-41 to 1-43,1-47,1-53 to 1-56,1-62 to 1-64,1-66,1-73,1-77,1-79,1-90,1-93,1-97 to 1-104,1-106 to 1-108,1-111,1-115,1-119,1-120,1-124,1-127,1-129,1-131,1-148,1-150,1-152,1-156,1-160,1-161,1-164,1-165,1-167,1-170,1-172,1-174,1-175,1-190,1-205,1-516,2-1,2-14,3-2,3-4,3-6,3-9,3-10,3-12,3-19,3-20,3-23,4-10 and 6-1 to 6-3 carry out this test respectively, and all compound exhibits control index under 500ppm concentration is 4 or 5 effect.Carry out this test for above-claimed cpd No.1-34, this compound exhibits control index under 200ppm concentration is 4 effect.Experimental example 3: to the test of the preventive and therapeutic effect of rice blast

Paddy rice (is cultivated plants: Nihonbare) cultivate in diameter is the plastic tub of 7.5cm, and when reaching the 1.5-leafage during stage, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.After this chemical solution drying (with using on the same day or second day), the conidial suspension of inoculation Rice Blast Fungus (Pyricularia Oryzae), and keeping in 20 ℃ inoculation tank 24 hours remains in 20 ℃ the thermostatic chamber then.After inoculation 5-7 days, the number of observation lesion, and determine control index according to above-mentioned judgement criteria.Carry out this test respectively for above-claimed cpd No.1-6,1-9,1-13,1-14,1-28,1-45,1-47,1-52,1-53,1-55,1-56,1-62,1-63,1-66,1-75,1-77,1-79,1-109,1-119,1-164,2-1,2-2,3-25 and 4-19, all compound exhibits control index under 500ppm concentration is 4 or 5 effect.

Experimental example 4: to the test of the preventive and therapeutic effect of kidney bean gray mold

Kidney bean (is cultivated plants: Taisyou Kintoki) cultivate in diameter is the plastic tub of 15cm, and when main lobe is fully grown, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.After this chemical solution drying (with using on the same day or second day), the suspension (being diluted with water to potato-glucose extracting solution of 50%) of spore of inoculation botrytis cinerea (Botrytis Cinerea), and remain in 20 ℃ the thermostatic chamber.After inoculation 3 days, the length (mm) of observation lesion, and determine control index according to above-mentioned judgement criteria.For above-claimed cpd No.1-11,1-15,1-17,1-20,1-22,1-27,1-41,1-43,1-52,1-80,1-99,1-102,1-112 to 1-115,1-117,1-118,1-120,1-125,1-131,1-136,1-160,1-162,1-169,1-172,1-176,1-180,1-182,1-186 to 1-189,1-273,2-2,2-9,2-13,2-14 and 7-6 carry out this test respectively, and all compound exhibits control index under 500ppm concentration is 4 or 5 effect.

Experimental example 5: to the test of the preventive and therapeutic effect of kidney bean stem rot

Kidney bean (is cultivated plants: Taisyou Kintoki) cultivate in diameter is the plastic tub of 15cm, and when main lobe is fully grown, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.After this chemical solution drying (with using on the same day or second day), the mycelia body disc of inoculation sclerotium germ (Sclerotinia sclerotiorum), and remain in 20 ℃ the thermostatic chamber.After inoculation 3 days, the length (mm) of observation lesion, and determine control index according to above-mentioned judgement criteria.For above-claimed cpd No.1-1,1-4,1-7,1-10,1-16,1-18,1-19,1-21,1-26,1-30 to 1-33,1-36,1-38,1-42,1-44,1-46,1-57,1-60,1-64,1-69,1-71,1-73,1-75,1-80,1-86,1-93,1-96 to 1-98,1-103 to 1-105,1-108,1-111 to 1-114,1-117,1-118,1-123,1-126,1-128,1-129,1-133 to 1-136,1-141 to 1-144,1-146,1-149,1-150,1-159,1-161 to 1-163,1-165 to 1-171,1-176,1-180,1-181,1-186,1-188,1-208,1-209,1-271,1-273,1-276,1-535,2-1,2-3,2-4,2-10,2-11,2-13,3-2,3-3,3-6,3-23,3-26,4-10,6-2,6-3,7-2,7-4,7-6 to 7-8 and 7-66 carry out this test respectively, and all compound exhibits control index under 500ppm concentration is 4 or 5 effect.

Experimental example 6: to the test of the preventive and therapeutic effect of wheat glume blight

Wheat (is cultivated plants: Norin-61-go) cultivate in diameter is the plastic tub of 7.5cm, and reach the 1.5-leafage during stage when it, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.After this chemical solution drying (with using on the same day), spray and inoculate the conidial suspension of clever withered septoria musiva (Septoria nodorum), and in 20 ℃ inoculation tank, kept 72 hours, remain on then in 20 ℃ the thermostatic chamber.After inoculation 5-10 days, observe the number of lesion, and determine control index according to above-mentioned judgement criteria.Carry out this test for above-claimed cpd No.1-179 and 1-189, all compound exhibits control index under 500ppm concentration is 4 or 5 effect.

Experimental example 7: to the test of the preventive and therapeutic effect of rice sheath blight disease

Paddy rice (is cultivated plants: Nihonbare) cultivate in diameter is the plastic tub of 7.5cm, and reach the 5-leafage during stage when it, use the chemical solution of 10ml by spray gun, this chemical solution has amide derivatives or its salt of the formula (I) that is adjusted to predetermined concentration.After this chemical solution drying (with using on the same day or second day), the mycelia body disc of the dry thread Pyrenomycetes (Rhizoctonia solani) cultivated in advance inserted in the leaf sheath and with rope fix, and in 25 ℃ inoculation tank, keep.After inoculation 5-7 days, the length of observation lesion, and determine control index according to above-mentioned judgement criteria.Carry out this test respectively for above-claimed cpd No.1-130,1-137 and 3-3, all compound exhibits control index under 500ppm concentration is 4 or 5 effect.

The ingredients embodiment of the present composition will be described below.But weight ratio, ingredients type etc. is not restricted to following examples.

Ingredients embodiment 1

(1) formula (I) compound

20 weight parts

(2) clay 72 weight parts

(3) sodium lignosulfonate 8 weight parts

Said components is mixed equably, obtain wettable powder.

Ingredients embodiment 2

(1) formula (I) compound

5 weight parts

(2) talcum 95 weight parts

Said components is mixed equably, obtain pulvis.

Ingredients embodiment 3

(1) formula (I) compound

20 weight parts

(2) N, N '-N,N-DIMETHYLACETAMIDE 20 weight parts

(3) polyoxyethylene alkyl phenyl ether

10 weight parts

(4) dimethylbenzene 50 weight parts

Said components is mixed equably and dissolve, obtain emulsifiable concentrate.

Ingredients embodiment 4

(1) clay 68 weight parts

(2) sodium lignosulfonate 2 weight parts

(3) polyxyethylated aryl-sulfate

5 weight parts

(4) fine silica 25 weight parts

The mixture of said components is mixed according to 4: 1 weight ratio with formula (I) compound, obtain wettable powder.

Ingredients embodiment 5

(1) formula (I) compound

50 weight parts

(2) oxygen base polyoxyethylene alkylphenyl base phosphoric acid ester-trolamine

2 weight parts

(3) siloxanes 0.2 weight part

(4) water 47.8 weight parts

Said components is mixed equably and pulverize, obtain material solution, and further to wherein adding:

(5) poly carboxylic acid sodium 5 weight parts

(6) anhydrous sodium sulphate 42.8 weight parts

Mix equably then, granulation is also dry, obtains water dispersible particle.

Ingredients embodiment 6

(1) formula (I) compound

5 weight parts

(2) polyoxyethylene octyl phenyl ether

1 weight part

(3) polyoxyethylated phosphoric acid salt

0.1 weight part

(4) calcium carbonate granule

93.9 weight part

Said components (1) to (3) is mixed earlier equably,, the mixture after the dilution is sprayed onto on the component (4), and removes acetone, obtain particle with the acetone diluted of appropriate amount.

Ingredients embodiment 7

(1) formula (I) compound

2.5 weight part

(2) N-N-methyl-2-2-pyrrolidone N-2.5 weight parts

(3) soya-bean oil 95.0 weight parts

Said components is mixed equably and dissolve, obtain the ingredients of ultralow volume.

Ingredients embodiment 8

(1) formula (I) compound

20 weight parts

(2) poly-alkylphenol phosphoric acid ester-trolamine 2 weight parts of oxygen baseization

(3) siloxanes 0.2 weight part

(4) xanthan gum 0.1 weight part

(5) ethylene glycol 5 weight parts

(6) water 72.7 weight parts

Said components is mixed equably and pulverize, obtain water base suspending concentrate.

Claims

1. amide derivatives or its salt of formula (I-α):

A wherein ^αBe not replace or by X ^αThe phenyl that replaces; The thienyl that B is replaced by Y; X ^αBe fluorine, chlorine, iodine, alkyl, haloalkyl, alkynyl, hydroxyl, alkoxyl group, halogenated alkoxy, the alkoxyl group alkoxyl group, cycloalkyl, nitro, the phenyl alkynyl, the pyridyl oxygen base that does not replace or replaced by haloalkyl, alkyl-carbonyl oxygen base, or heterocycle, heterocycle is randomly replaced by halogen, alkyl or alkyl-carbonyl; Y is a halogen, alkyl, haloalkyl, or alkoxyl group; R ¹And R ²Be alkyl independently of one another; R ³Be hydrogen; W ¹And W ²Each is oxygen naturally.

2. formula (I-α) amide derivatives that contains with good grounds claim 1 or salt are as the fungicidal composition of activeconstituents.

3. a method of controlling harmful fungoid comprises the formula according to claim 1 (I-α) amide derivatives or its salt that apply significant quantity.

4. the method for a controlling plant disease comprises the formula according to claim 1 (I-α) amide derivatives or its salt that apply significant quantity.

5. the method for a cover crop comprises the formula according to claim 1 (I-α) amide derivatives or its salt that apply significant quantity.

6. a method of improving crop yield comprises the formula according to claim 1 (I-α) amide derivatives or its salt that apply significant quantity.