Derivatives phenylalaninamide, methods for their production and agricultural or horticultural fungicide

 

(57) Abstract:

Describes the new derivatives phenylalaninamide represented by formula 1, where R1means a hydrogen atom or a C1-C6alkyl group, R2means a hydrogen atom, a C1-C6alkyl group, R3and R4each independently represents C1-C6alkyl group, a C2-C6cycloalkyl group2-C6CNS group or1-C4halogenating group, or R3and R4together with the carbon atom to which they are attached, form cycloalkyl group 5-7-membered cycle which may be substituted WITH1-C6alkyl group, Q represents a cyano or a group of the formula-COR5where R5means a hydroxy-group, WITH1-C6alkyl group, a C1-C6alkoxygroup, the amino group, WITH1-C6alkylamino or1-C6dialkylamino, X means a halogen atom, a C1-C6alkyl group, a C2-C6alkylamino group1-C4halogenating group, a hydroxy-group, WITH1-C6alkoxygroup,3-C6cycloalkanes,1-C4-C6allylthiourea,1-C6alkylsulfonyl group1-C6alkylsulfonyl group, amino group, WITH1-C6alkylamino,1-C6dialkylamino, a nitrogroup, cyano, aryl group, heteroaryl group selected from pyridyl or pyrrolyl, alkylcarboxylic group, arylcarbamoyl group, taylorsville group; each of E and Z independently represents a hydrogen atom or halogen atom, n is an integer of 0-3, excluding the case when R3and R4are triptorelin group at the same time, and provided that when R1and R2both represent hydrogen, both Y and Z represent a hydrogen atom, and n represents an integer of 1-3. The compounds of formula 1 exhibit superior fungicidal activity compared with conventional fungicides against particularize rice and such diseases and at the same time do not interfere with the growth of desirable plants. Describes a method of their production and agricultural or horticultural fungicides on the basis of these compounds. 4 C. and 4 h.p. f-crystals, 32 PL.

The present invention relates to new derivatives of phenylalkylamines and agricultural or horticultural fungicide containing nobiletin)-2-(2,4-dichlorophenyl)ndimethylacetamide and similar compounds have been known as intermediate products 3-arylpyrimidine-2,4-diones (patent application Japan, the first publication, N Hei 6-220004 and patent application Japan, the first publication N Hie 6-263731); however, the usefulness of these compounds as agricultural or horticultural fungicides are not known at all.

Recently fungicidal activity of conventional fungicides may deteriorate due to the occurrence of resistant fungi after repeated use of these fungicides. For this reason, and also due to environmental problems, it is desirable to offer a new fungicide, which can effectively suppress harmful fungi even at low concentrations.

To develop an agent that has superior fungicidal activity compared with conventional fungicides, the authors of the present invention have synthesized various new derivatives phenylalkylamines and has conducted extensive research in relation to their effect on the biological activity of fungi. As a result, the authors of the present invention have found that the new compounds of the present invention have excellent fungicidal activity against pyricularia rice and similar diseases, at the same time do not interfere with the growth of desirable plants.

Disclosure of the invention

This izobreteny the o atom of hydrogen or C1-C4alkyl group,

R2represents a hydrogen atom, a C1-C6alkyl group, a C2-C6cycloalkyl group or a C1-C4halogenating group

each of R3and R4independently represents C1-C6alkyl group, a C2-C6alkenylphenol group, C3-C6cycloalkyl group, C2-C6alkoxyalkyl group or a C1-C4halogenating group or

R3and R4together with the carbon atom to which they are attached, form cycloalkyl group from 5-membered to 7-membered ring which may be substituted C1-C6alkyl group),

Q represents a cyano or a group of the formula: -COR5(where R5represents a hydroxy-group, C1-C6alkyl group, a C1-C6alkoxygroup, C2-C6alkenylacyl, C2-C6alkyloxy, C3-C6cycloalkylation, fenoxaprop, benzyloxy, an amino group, a C1-C6alkylamino or C1-C6dialkylamino),

X represents a halogen atom, a C1-C6alkyl group, a C2-C6alkenylphenol group, C1
-C6alkoxygroup, C2-C6alkenylacyl, C2-C6alkyloxy, C3-C6cycloalkylation, C1-C4halogenlampe, alloctype (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), heterokaryosis (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), C1-C6allylthiourea, C1-C6alkylsulfonyl group, C1-C6alkylsulfonyl group, C1-C4halogenation, killigrew (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), heteroanalogues (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or ATO 1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), arylsulfonyl group (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), amino group, C1-C6alkylamino, C1-C6dialkylamino, a nitrogroup, cyano or aryl group (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), a heteroaryl group (which may be substituted, C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom, aracelio group (which may be substituted C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), C1-C6alkylcarboxylic group, arylcarbamoyl group (which may be substituted C1-C1-C6alkyl group, a C1-C4halogenoalkanes group, C1-C6alkoxygroup, a cyano, a nitro-group or a halogen atom), a formyl group or a C1-C6alkoxycarbonyl group

each of Y and Z independently represents a hydrogen atom, a C1-C6alkyl group, a C1-C4halogenating group, C1-C6alkoxygroup, a cyano, a nitro-group or halogen atom, and

n is an integer of 0-3,

except in the case when R3and R4are simultaneously triptorelin group, and

provided that when R1and R2represent a hydrogen atom simultaneously, then both Y and Z represent a hydrogen atom, and n is an integer of 1-3,

as well as the agricultural or horticultural fungicide comprising the derived phenylalaninamide as the active ingredient.

The terms used in the present invention are defined below. In the present invention, for example, in the case of the expression "C1-C6"the group is shown after the "C1-C6"has from 1 to 6 carbon atoms is unbranched or branched chain, including, but not limited to, methyl group, ethyl group, n-sawn group, isopropyl group, n-boutelou group, isobutylene group, sec-boutelou group, tert-boutelou group, n-pentelow group, isopentyl group, neopentyl group, n-hexoloy group, isohexyl group, 3,3-dimethylbutyl group, etc.

As "C3-C6cycloalkyl group" here we can mention, for example, cyclopropyl group, cyclopentyl group, tsiklogeksilnogo group, etc.

The term "C1-C4halogenating group" is used here to denote a halogen-substituted alkyl groups with unbranched or branched chain, including, but not limited to, formeterol group, chloromethylene group, deformational group, dichloromethylene group, triptorelin group, pentafluorothiophenol group, etc.

The term "C2-C6alkenylphenol group" is used here to denote alkenylphenol group with unbranched or branched chain, including, but not limited to, vinyl group, 1-propenyloxy group, allyl group, Isopropenyl group, 1-butenyloxy group, 2-butenyloxy group, etc.

As the "aryl group" may be mentioned are, for example, phenyl group, 1-naftalina group, 2-naftalina group, etc.

As the "heteroaryl group" here we can mention, for example, 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group, 2-follow group, 3-follow group, 2-thienyl group, 3-thienyl group, 1-pyrrole group, 2-pyrrole group, 3-pyrrole group, etc.

The term "kalkilya group" is used here to denote aryl (has the same meaning as defined above) substituted C1-C3alkyl groups with unbranched or branched chain, including, but not limited to, benzyl group, fenetylline group, 1-naphthylmethyl group, 2-naphthylmethyl group, etc.

The term "halogen atom" is used here to denote a fluorine atom, chlorine atom, bromine atom or iodine atom.

The term "C1-C6alkoxygroup" is used here to denote actigraph, n-propoxylate, isopropoxy, n/butoxypropyl, isobutoxy, sec-butoxypropyl, tert-butoxypropyl, n-pentyloxy, isopentylamine, n-hexyloxy etc.

The term "C2-C6alkenylacyl" is used here to denote alkenylacyl with unbranched or branched chain, including, but not limited to, alliancegroup, isopropenylacetate, 2-butenyloxy etc.

The term "C2-C6alkyloxy" is used here to denote alkenylacyl with unbranched or branched chain, including, but not limited to, 2-propenyloxy, 2-butenyloxy, 3-butenyloxy etc.

As "C3-C6cycloalkylcarbonyl" here we can mention, for example, cyclopropylamino, cyclopentyloxy, cyclohexyloxy etc.

The term "C1-C4halogenlampe" is used here to denote a halogensubstituted alkoxygroup with unbranched or branched chain, including, but not limited to, formatexpr, dipterocarp, cryptometer, pentafluoropropyl etc.

As alloctype" este "heterokaryosis" can be mentioned, for example, 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy, 2-ferrochrome, 3-ferrochrome, 2-taylortype, 3-taylortype etc.

The term "arancelaria" is used here to denote aryl-substituted C1-C3alkoxygroup with unbranched or branched chain, including, but not limited to, benzyloxy, penetrometry etc.

The term "C1-C6allylthiourea" is used here to denote ancilliary with unbranched or branched chain, including, but not limited to, methylthiourea, ethylthiourea, n-PropertyGroup, isopropylthio, n-butylthiourea, isobutylthiazole, sec-butylthiourea, tert-butylthiourea, n-vexillographer etc.

The term "C1-C6alkylsulfonyl group" is used here to denote alkylsulfonyl group with unbranched or branched chain, including, but not limited to, methylsulfinyl group, ethylsulfinyl group, n-propylsulfonyl group, isopropylphenyl group, n-butylsulfonyl group, isobutylamino group, sec-butylsulfonyl group, tert-butylsulfonyl group, n-Gades to denote alkylsulfonyl group with unbranched or branched chain, including, but not limited to, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylphenyl group, n-butylsulfonyl group, isobutylamino group, sec-butylsulfonyl group, tert-butylsulfonyl group, n-hexylaniline group, etc.

The term "C1-C4halogenlampe" is used here to denote a halogensubstituted ancilliary with unbranched or branched chain, including, but not limited to, formattertype, deformationof, triptoreline, pentitentiary etc.

As aristocraty" here we can mention, for example, phenylthiourea, 1-naphthylthiourea, 2-naphthylthiourea or the like.

As heteroanalogues" can be mentioned, for example, 2-pyridylthio, 3-pyridylthio, 4-pyridylthio, 2-guiltygroup, 3-guiltygroup, 2-teenietop, 3-teenietop etc.

As arylsulfonyl group" here we can mention, for example, phenylsulfinyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, etc.

As arylsulfonyl group" here tx2">

The term "C1-C6alkylamino" is used here to denote alkylamino with unbranched or branched chain, including, for example, methylaminopropyl, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-hexylamino etc.

As "C1-C6dialkylamino" can be mentioned, for example, dimethylaminopropyl, diethylaminopropyl, dipropylamino, dibutylamino etc.

The term "C1-C6acylcarnitine group" is used here to denote alkylcarboxylic group with unbranched or branched chain, including, for example, acetyl group, propionyl group, Butylimino group, isobutylamino group, etc.

As arylcarboxylic group" here we can mention, for example, benzoyloxy group, 1-afterburning group, 2-afterburning group, etc.

As heteroarylboronic group" here we can mention, for example, 2-pyridylcarbonyl group, 3-pyridylcarbonyl group, 4-pyridylcarbonyl group, 2-fuelleborni group, 3-fullcirclemagazine.org group" is used here to denote alkoxycarbonyl group with unbranched or branched chain, including, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxyethanol group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-ventilatsioonile group, n-hexyloxyphenyl group, etc.

Compounds represented by formula (1) according to the present invention can exist as optical isomers due to the presence of one or more chiral centers in the molecule. The present invention relates to all such diastereomers, the enantiomers and their mixtures.

Preferred compounds represented by formula (1) according to the present invention, are compounds in which:

R1represents a hydrogen atom or methyl group,

R2represents a hydrogen atom, methyl group or ethyl group,

R3represents methyl group, ethyl group or n-sawn group

R4represents methyl group, ethyl group, n-sawn group, isopropyl group, n-boutelou group, isobutylene group, sec-boutelou group, tert-boutelou group, cyclepro the carbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, sec-butoxycarbonyl group or karbamoilnuyu group,

X represents fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, isopropyl group, isobutylene group, sec-boutelou group, tert-boutelou group, cyclopentyloxy group, tsiklogeksilnogo group, triptorelin group, a methoxy group, ethoxypropan, n-propoxylate, isopropoxy, dipterocarp, cryptometer, fenoxaprop, methylthiourea, ethylthiourea, isopropylthio, dimethylaminopropyl, diethylaminopropyl, a nitrogroup, cyano, phenyl group, acetyl group or benzoyloxy group

each of Y and Z independently represents a hydrogen atom or a fluorine atom, and

n is an integer of 1-3.

The following are examples of compounds represented by formula (1) according to the present invention are listed in tables 1-24. However, it should be clear that the present invention is not limited to these compounds. The numbers of compounds, the data in the tables will be shown later in the description.

In the tables, "Me" means IU which includes ISO-propyl group,

"Bu-n" means n-boutelou group

"Bu-i" denotes isobutylene group

"Bu-s" means second-boutelou group

"Bu-t" refers to tert-boutelou group

"Pr-cyc" means cyclopropyl group

"Pen-cyc" means cyclopentyloxy group

"Ph" denotes a phenyl group,

"4-OPh(2-Cl)" refers to 4-(2-chlorophenyl)oxygraph,

"4-O(2-Py)" refers to 4-(2-pyridyl)oxygraph,

"4-O(5-CF3,2-Py)" refers to 4-(5-trifluoromethyl-2-pyridyl)- oxygraph,

"4-O(3-Py)" refers to 4-(3-pyridyl)oxygraph,

"4-O(4-Py)" refers to 4-(4-pyridyl)oxygraph,

"4-SPh(2-Cl)" refers to 4-(2-chlorophenyl)togroup,

"4-S(O)Ph(2-Cl)" refers to 4-(2-chlorophenyl)sulfinyl group

"4-SO2Ph(2-Cl)" refers to 4-(2-chlorophenyl)sulfonyloxy group

"4-S(2-Py)" refers to 4-(2-pyridyl)togroup,

"4-Ph(4-CF3" refers to 4-(4-triftormetilfullerenov) group

"4-(2-Py)" refers to 4-(2-pyridyloxy) group

"4-(2-Fur)" refers to 4-(2-follow) group

"4-(2-Thi)" refers to 4-(2-thienyl) group

"4-COPh(2-IU)" refers to 4-(2-methylbenzoyl) group

"4-CO(3-Py)" refers to 4-(3-pyridyl)carbonyl group,

"4-CO(2-Fur)" refers to 4-(2-furyl)carbonyl group,

"4-CO(2-Thi)" refers to 4-(2-thienyl) is pyrrolidino) group.

Connection NN C-42, C-43, C-196, C-197 C-198 C-199 are optically active compounds having the rotation angles []2D2= +32,7o(c = 0.5, CHCl3), []2D2= - 27.3 hwto(c = 0.5, CHCl3), []2D2= +9,8o(c = 1,0, CHCl3), []2D2= +23,4o(c = 1,0, CHCl3), []2D2= -8,4o(c = 1,0, CHCl3and []2D2= -19,9o(c = 1,0, CHCl3), respectively.

Connection NN C-16, C-17, C-18, C-21, C-24, C-27, C-34, C-39, C-47, C-51, C-54, C-62, C-66, C-71, C-73, C-75, C-81, C-88, C-92, C-94, C-99, C-102, C-106, C-108, C-112, C-114, C-117, C-122, C-129, C-131, C-140, C-157, C-161, C-165, C-169, C-171, C-174, C-177, C-179, C-181, C - 184, C-187, C-189 C-193 C-196, C-198, C-200, D-40, D-63, D-91, D-119, E-30 and E-37 is A configuration of the diastereomers. Connection NN C-19, C-22, C-25, C-28, C-35, C-40, C-48, C-52, C-55, C-63, C-67, C-72, C-74, C-76, C-82, C-89, C-93, C-95, C-100, C-103, C-107, C-109, C-113, C-115, C-118, C-123, C-130, C-141, C-158, C-162, C-166, C-170, C-172, C-175, C-178, C-180, C-182, C-185, C-188, C-190, C-194 C-197 C-199 C-201, D-41, D-64, D-92, D-120, E-31 and E-38 are the B-configuration of the diastereomers. In addition, other compounds having two or more asymmetric carbon atoms, are mixtures of diastereomers.

"A-configuration diastereoisomer" means iskopaemye the diastereoisomer allocated column chromatography on silica gel the measures" refers to the highly polar diastereoisomer, allocated in the same way as above.

Compounds represented by formula (1), can be synthesized according to, for example, methods of preparation, are shown below.

The method of obtaining 1

< / BR>
where R1, R2, R3, R4X, Y, Z, Q and n have such values as defined above).

The compounds of formula (1) according to the present invention can be obtained by reaction of the derivatives phenylalkanoic acids represented by the formula (2), and amines represented by the formula (3), using a condensing agent in the presence of a catalyst and/or base, if necessary.

This reaction can be carried out in a solvent, this solvent may be any solvent which does not inhibit the reaction, for example, hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene and the like, halogenated hydrocarbons such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene and the like, ethers such as diethyl ether, diisopropyl ether, dimethyl ether of ethylene glycol, tetrahydrofuran, dioxane and the like, ketones such as acetone, IU, tracecut and the like, NITRILES such as acetonitrile, propionitrile and the like, aprotic polar solvents such as dimethylsulfoxide, N,N-dimethylformamide, sulfolane and the like, and mixtures of solvents, combining solvents selected from the above.

As the condensing agent include the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N, N'-dicyclohexylcarbodiimide, carbonyldiimidazole, chloride 2-chloro-1,3-dimethylimidazole etc.

As catalysts may be mentioned, for example, 4-dimethylaminopyridine, 1-hydroxybenzotriazole, dimethylformamide, etc.

The base can be any base type normally used in this type of reaction. We can mention, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and the like, hydroxides of alkaline earth metals such as calcium hydroxide and the like, carbonates of alkali metals such as sodium carbonate, potassium carbonate and the like, organic bases such as triethylamine, trimethylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, 1,5-diazabicyclo/4.3.0/non-5-ene (DBN), 1,8-diazabicyclo/5.4.0/undec-7-ene (DBU) and the like, and Amin is mperature from -50 to 150oC, preferably from 0 to 60oC. the reaction Time is preferably in the range from 1 to 30 hours.

Below is an explanation of the method of synthesis of each of the starting compounds.

Compounds represented by formula (2), can be synthesized, for example, by hydrolysis of phenylmalonate using alkali, heating the hydrolyzed product and the subsequent decarbonylation heated product. This method of obtaining described in Journal of Organic Chemistry, vol. 13, p. 763 (1948); Organic Syntheses, vol. 3, p. 557, 1955; the patent application of Japan, first publication, No. Sho 40-7491 and Synthesis, vol. 6, p. 456, 1982.

In addition, compounds represented by formula (3), can be synthesized, for example, using ketone, sodium cyanide and ammonium chloride in accordance with the method Strecker, which is described in Organic Synthesis, vol. 3, p. 88, 1955; Journal of Medicinal Chemistry, vol. 9, p. 911, 1966 Tetrahedron Letters, vol. 17, p. 1455, 1977.

The method of obtaining 2

< / BR>
(where R1, R2, R3, R4X, Y, Z, Q and n have such values as defined above, and L represents a halogen atom).

Compounds represented by formula (1) according to the present invention can be obtained by reaction of halides phenylalkanoic acids represented by formulaterules can be any solvent, which does not inhibit the reaction, for example hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene and the like, halogenated hydrocarbons such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene and the like, ethers such as diethyl ether, diisopropyl ether, dimethyl ether of ethylene glycol, tetrahydrofuran, dioxane and the like, ketones such as acetone, methyl ethyl ketone, methylisobutylketone, methyl isobutyl ketone and the like, esters such as methyl acetate, the ethyl acetate and the like, NITRILES such as acetonitrile, propionitrile and the like, aprotic polar solvents such as dimethylsulfoxide, N, N-dimethylformamide, sulfolane and the like, and mixtures of solvents, combining solvents selected from the above.

The base can be any base type normally used in this type of reaction. We can mention, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and the like, hydroxides of alkaline earth metals such as calcium hydroxide and the like, carbonates of alkali metals, tetramin, N,N-dimethylaniline, pyridine, N-methylpiperidine, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) and the like, and amines, such as triethylamine, pyridine, N-methylpiperidine and the like.

This reaction is carried out at a temperature of from -50 to 150oC, preferably from 0 to 60oC. the reaction Time is preferably in the range from 1 to 30 hours.

The following is an explanation of the method of obtaining the starting compounds used in the specified method.

Halides phenylalkanoic acids represented by the formula (4), can be obtained by reaction phenylalkanoic acids represented by the formula (2) obtained, for example, the above-mentioned method, and halogenation agent such as thionyl chloride, pentachloride phosphorus, tribromide phosphorus or the like.

The method of obtaining 3

< / BR>
(where R1, R2, R3, R4X, Y, Z and n have such values as defined above, and R represents a C1-C6alkyl group).

Compounds represented by formula (1-2) of the present invention, can be obtained by reaction of compounds represented by formula (1-1) of the present invention, and alcohols represented by the formula (5), which nasyt any solvent, which does not inhibit the reaction, for example alcohols, such as methanol, ethanol, propanol, isopropanol, butanol and the like, hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene and the like, halogenated hydrocarbons such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene and the like, ethers such as diethyl ether, diisopropyl ether, dimethyl ether of ethylene glycol, tetrahydrofuran, dioxane and the like and mixtures of solvents, combining solvents, selected from the above.

This reaction is carried out at a temperature of from -50 to 150oC, preferably from 0 to 120oC. the reaction Time is preferably in the range from 1 to 20 hours.

The best ways of implementing the present invention

The following are examples of preparing compounds of the present invention.

Example obtain 1

Synthesis of N-(1-cyano-1,2-dimethylpropyl)-2-(4-biphenylyl)ndimethylacetamide (connection N A-87)

1.1 g (5.7 mmol) of the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide are added to a solution containing 1.0 g (4.5 mmol) 4-biphenylacetic acid, restoreable 0.5 g (4.7 mmol) of 2-amino-2,3-dimethylvaleronitrile and the whole mixture is stirred for 3 hours at room temperature. After completion of the reaction to the resulting mixture, water is added and the methylene chloride layer is washed with water and then dried over anhydrous magnesium sulfate. The methylene chloride is removed from the organic layer under reduced pressure. The residue is purified column chromatography on silica gel, thus obtaining 1.1 g (yield: 76%) of target compound having a melting point of 151-152oC.

Example of getting 2

Synthesis of N-(1-cyano-1,2-dimethylpropyl)-2-(4-bromophenyl)propionamide (connection NN C-47 C-48)

0.9 g (8.0 mmol) of 2-amino-2,3-dimethylvaleronitrile and 0.8 g (7.9 mmol) of triethylamine dissolved in 20 ml of tetrahydrofuran. To this mixture, which is stirred at 10oC, for 5 minutes, added dropwise to 1.5 g (6.0 mmol) of 2-(4-bromophenyl)Propionaldehyde. After the addition, the reaction mixture is stirred for 5 hours at room temperature. The reaction mixture was concentrated and then add water. The organic layer is extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The ethyl acetate organic layer removed under reduced pressure. The residue is purified column chromatography on silica gel, thereby obtaining 0.45 g (yield 24%) A-configuration diastereoisomer (discobole the polar product) having a melting point 121-123oC.

Example of getting 3

Synthesis of N-(1-carbarnoyl-1-ethylpropyl)-2-(4-chlorophenyl)propionamide (compound N D-32)

2.3 g (18 mmol) of 2-amino-2-ethylbutylamine 2.0 g (20 mmol) of triethylamine are suspended in 50 ml of tetrahydrofuran. Tertrahydrofuran ring solution (10 ml) containing 3.0 g (15 mmol) dissolved in 2-(4-chloroethyl)propionitrile, is added dropwise during 10 minutes to a suspension, which was stirred at room temperature. After the addition, the reaction mixture is stirred for 3 hours at room temperature. The reaction mixture was concentrated and then add water. The organic layer is extracted with chloroform and then dried over anhydrous magnesium sulfate. The chloroform is removed from the organic layer under reduced pressure. The obtained crystal was washed with diisopropyl ether, thereby obtaining of 4.2 g (yield 95%) of the desired product having a melting point 116-118oC.

Example 4

Synthesis of methyl 2-[1-(4-chlorophenyl)ethylcarbodiimide] -2-ethylbutyrate (compound N D-28)

0.6 g (2.0 mmol) N-(1-carbarnoyl-1-ethylpropyl)-2-(4 - chlorophenyl)propionamide dissolved in 10 ml saturated with hydrogen chloride methanol. The solution CVU. The organic layer is extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The ethyl acetate organic layer removed under reduced pressure. The residue is purified column chromatography on silica gel, thereby obtaining 0.5 g (yield 81%) of the desired product having a melting point of 98-99oC.

Example of getting 5

Synthesis of N-(1-cyano-1-cyclopropylethyl)-2-(4-chlorophenyl)-2-methylpropionamide (compound N E-9)

0.25 g (2.3 mmol) of 2-amino-2-cyclopropanecarbonitrile and 0.3 g (3.0 mmol) of triethylamine dissolved in 20 ml of tetrahydrofuran. Dropwise to the mixture, which was stirred at 10oC, for 5 minutes, add 0.5 g (2.3 mmol) of 2-(4-chlorophenyl)-2-methylpropionamide. After graduating added dropwise, the reaction mixture is stirred for 3 hours at room temperature. The reaction mixture was concentrated and then add water. The organic layer is extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The ethyl acetate organic layer removed under reduced pressure. The residue is purified column chromatography on silica gel, thereby obtaining 0.5 g (75% yield) of the desired product having a melting point of 93-94oC.

An example of obtaining 6

Syntuhroid 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide are added to a solution, containing 1.0 g (4.9 mmol) of 4-triftormetilfullerenov acid, dissolved in 50 ml of methylene chloride, at room temperature, and the mixture is then stirred for 10 minutes. There was added 0.9 g (5.2 mmol) of isopropyl-2-amino-2,3-dimethylbutyramide and the whole mixture is stirred for 3 hours at room temperature. After completion of the reaction, to the reaction mixture, water is added. The methylene chloride layer is washed with water and then dried over anhydrous magnesium sulfate. The methylene chloride is removed under reduced pressure. The residue is purified column chromatography on silica gel, thereby obtaining 1.4 g (yield 80%) of the desired product having a melting point of 122-123oC.

Agricultural and horticultural fungicides of the present invention comprise as active ingredients derived phenylalkylamines represented by the formula (1). When the compounds of the present invention are used as agricultural and horticultural fungicides, these compounds acting as active ingredients, can be prepared in the form of a suitable ready preparative forms depending on the purpose. The active ingredient is usually diluted with an inert liquid or solid carrier and, if the m in ready preparative form for example, fine powder, wettable powder, emulgirujushchie concentrate, granules, etc.

As a suitable carrier materials used in the finished preparative form, mention can be made of solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, siliceous sand, ammonium sulfate, urea or the like, and liquid media, such as isopropyl alcohol, xylene, cyclohexanone, methylnaphthalene and the like. As surfactants and dispersants can be mentioned dinaftiletilena, sulfates of alcohols, alkylarylsulfonate, ligninsulfonate, polyoxyethyleneglycol ethers, polyoxyethyleneglycol ethers, monoalkylated of polyoxyethylenesorbitan and the like. As auxiliary agents may be mentioned the carboxymethylcellulose and the like. Turned into ready preparative form of agricultural or horticultural fungicide of the present invention can be diluted diluted to a suitable concentration, or can be applied directly.

Agricultural or horticultural fungicide of the present invention can be used DLNA choose according to needs. When the fungicide is transformed into the form of a finely divided powder or granules, the content of the active ingredient is preferably from 0.1 to 20% by weight. For mulgirigala concentrate or wettable powder of the active ingredient are preferred in an amount of 5 to 80 mass%.

The dose of the agricultural or horticultural fungicide of the present invention may vary depending on the type of connection, type of pest or disease that you want to suppress, the nature of the pest or disease, the extent of the damage, environmental conditions, forms of used drug, and the like. When agricultural or horticultural fungicide of the present invention is used directly in the form of powder or granules, it is recommended that the dose of the active ingredient was appropriately selected within the range from 0.1 to 5 kg per 10 ar, preferably in the range of from 1 g to 1 kg per 10 ar. In addition, when the fungicide of the present invention is in the form of a liquid, such as emulsifiable concentrate or wettable powder, it is recommended that the dose of the active ingredient was appropriately selected within the range of from 0.1 hours/million to HIE of the present invention in the above-mentioned ready preparative form can suppress plant diseases, caused by pathogenic fungi Oomycetes, Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes.

The following are examples of fungi, but they are not limited by these fungi: Pyricularia such as mushrooms of piricularia rice (Pyricularia oryzae), Sphaerotheca, such as fungi powdery mildew of cucumber (Sphaerotheca fuliginea), Venturia, such as mushrooms scab of apples (Ventura inaequalis), Gibberella, such as mushrooms disease "bakanae" (Gibberella fujikuroi), Botrytis, such as mushrooms gray rot of cucumbers (Botrytis cinerea), Alternaria, such as mushrooms black spots Sarepta mustard (Alternaria Brassicicola), Rhizoctonia, such as fungi Rhizoctonia rice (Rhizoctonia solani), Puccinia, such as the rust fungi (Puccinia recondita), Pseudoperonospora, such as fungi downy mildew of cucumbers Pseudoperonospora cubensis).

In addition, the compounds of the present invention can be used as such or in combination with other fungicides, insecticides, herbicides, modifiers plant growth, fertilizers or the like. Further representative of the finished formulation is illustrated with reference to the following examples ready preparative forms, where all the "%" represents"% by mass".

Example composition 1: Fine powder

2% of compound A N-4, 5% of diatomaceous earth and 93% of clay mixed to obraze powder

50% of the compound N B-6, 45% of diatomaceous earth, 2% disastermanagement sodium and 3% ligninsulfonate sodium are mixed to form a homogeneous mixture and grind in a wettable powder.

Example of compound 3: Emulgirujushchie concentrate

30% of the compound N C-29, 20% of cyclohexanone, 11% polyoxyethyleneglycol ether, 4% of Las calcium and 35% of methylnaphthalene uniformly dissolved, thereby obtaining emulgirujushchie concentrate.

Example of compound 4: Granules

5% compound N B-34, 2% sodium salt of sulfate lauric alcohol, 5% ligninsulfonate sodium, 2% carboxymethylcellulose and 86% of clay are mixed and milled. To 100 parts by weight milled mixture is added 20 parts by weight of water. The resulting mixture is kneaded and turned into pellets of size from 14 to 32 mesh. using an extrusion granulator and then dried, obtaining the target pellets.

The following is an explanation of the effects that are agricultural or horticultural fungicides of the present invention, by referring to the examples of trials. In the examples of the test as a comparative connections use the connection described in the patent application of Japan, the first publication N Hei 6-220004.

oC for 24 hours and then in a greenhouse. On the fifth day after inoculation podkidyvajut the number of injuries on the fourth sheet. Inhibitory activity is calculated by equation 1. The evaluation results obtained in accordance with the standard evaluation, shown in table 25, are given in tables 26-28.

Equation 1

< / BR>
Example 2 test

The testing effect in pyricularia rice (Pyricularia oryzae) in the application of the dive.

Seedlings of rice (variety: Aichi Asahi) stage 2-th sheet dropped 4 spots at the rate of 3 seedlings per plot in white porcelain vessel having a diameter of 9 see the Seedlings allowed to develop and grow in the greenhouse. When the seedlings grow to stage a 3rd ltrace active ingredient was 300 g / 10 ar. When the fourth leaf is fully developed, the seedlings inoculant spore suspension of pyricularia rice (Pyricularia oryzae) and immediately placed in a moist chamber for incubation at 25oC for 24 hours and then in a greenhouse to induce defeat the disease. On the fifth day after inoculation count the number of damage on the fourth sheet. Inhibitory activity is calculated by equation 1. The evaluation results obtained in accordance with the standard evaluation, shown in table 25, are given in table 29.

The test example 3

Test for preventive effect on Apple parse (Yenturia inaequalis)

Apple seeds (variety: Jonathan) are sown at the rate of 4 grains in plastic pots having a diameter of 5.5 see Wettable powder obtained in accordance with example composition 2, was diluted with water to a concentration of 50 PM/million of active ingredient and then the resulting aqueous preparation spray, at a rate of 20 ml per pot, seedling apples that have fully developed this fourth sheet. After air drying, the seedlings inoculant spore suspension of fungi of the scab of Apple (Venturia inaequalis) and immediately placed in a moist chamber for incubation at 20oC for 48 hours and then in a greenhouse. On checkauth in accordance with the standard evaluation shown in table 30, with an index of morbidity and the number of infected leaves, the degree of damage calculated in accordance with equation 2 and inhibitory activity calculated in accordance with equation 3. Received inhibitory activity is evaluated according to standard estimates, shown in table 25, the results are given in table 31.

Equation (2):

< / BR>
Equation (3):

< / BR>
Example of getting 7

Synthesis of 2-(4-chlorophenyl)-N-(1-isopropyl-1-methyl-2-oxopropyl)ndimethylacetamide (compound N B-15).

4-chlorophenylalanine acid (1.0 g, 5.9 mmol) is dissolved in methylene chloride (50 ml). Thereto at room temperature, add the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.5 g, 7.8 mmol) and the mixture is stirred for 10 minutes. To the mixture is added 3-amino-3,4-dimethyl-2-pentanon (0.8 g, 6.2 mmol) and the mixture is stirred for 3 hours at room temperature. After completion of the reaction, to the reaction mixture, water is added. The methylene chloride layer is washed with water and dried over anhydrous magnesium sulfate. Thereafter, the methylene chloride is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 1.0 g (yield: 60%) C is 8

Synthesis of N-(1-cyano-1,2,2-trimethylpropyl)-2-(4-bromophenyl)propionamide (compound N C-51 and C-52).

2-amino-2,3,3-trimethylbutyramide (1.3 g, 10.0 mmol) and triethylamine (1.2 g, to 11.8 mmol) dissolved in tetrahydrofuran (20 ml). When the mixture stirred at 10oC, thereto is added dropwise within 5 minutes add the chloride of 2-(4-bromophenyl)propionic acid (1.5 g, 6.0 mmol). After the addition, the reaction mixture is stirred for 8 hours at room temperature. The reaction mixture is concentrated, water is added. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer is dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 0.3 g (yield: 15%) of diastereoisomer A configuration having a melting point in the range from 143 to 144oC and 0.85 grams (yield: 42%) of diastereoisomer configuration B, having a melting point in the range from 150 to 152oC.

Example of getting 9

Synthesis of N-(1-cyano-1,2-dimethylpropyl)-2-(4-trifloromethyl) propionamide (connection N C-122 and C-123).

2-amino-2,3-dimethylbutyramide (0.6 g, 5.3 mmol) and triethylamine (0.5 g, 5.3 mmol) restlet chloride 2-(4-trifloromethyl)propionic acid (1.1 g, 4.4 mmol). After completion of addition the reaction mixture is stirred for 4 hours at room temperature. The reaction mixture is concentrated and water is added. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, has resulted in 0.35 g (yield: 25%) of diastereoisomer A configuration (a configuration with a low polarity) having a melting point in the range from 97 to 98oC, and 0.4 g (yield: 29%) of diastereoisomer a configuration B configuration with high polarity) having a melting point in the range from 122 to 124oC.

Example 10

Synthesis of 2-(4-chlorophenyl)-N-(1-isopropyl-1-methyl-2-oxopropyl)propionamide (compound N D-25).

Hydrochloride 3-amino-3,4-Limeil-2-pentanone (1.3 g, 7.8 mmol) and potassium carbonate (2.6 g, to 18.7 mmol) dissolved in acetonitrile (20 ml). While stirring the mixture at 10oC thereto dropwise over 5 minutes add the chloride of 2-(4-chlorophenyl) propionic acid (1.7 g, 8.5 mmol). After completion of addition the reaction mixture is stirred for 2 hours at Comatorium with ethyl acetate. After an ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 1.3 g (yield: 56%) of the desired product having a melting point in the range from 140 to 143oC.

Example of getting 11

Synthesis of N- (1-isopropyl-1-methyl-2-oxopropyl)-2-(4-were)propionamide (compound N D-50).

Hydrochloride 3-amino-3,4-dimethyl-2-pentanone (1.0 g, 6.0 mmol) and potassium carbonate (2.1 g, of 15.2 mmol) dissolved in acetonitrile (20 ml). When the mixture stirred at 10oC, thereto is added dropwise within 5 minutes add the chloride of 2-(4-were)propionic acid (1.2 g, 6.6 mmol). After completion of addition the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture was concentrated and then add water to it. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 1.1 g (yield; 66%) of the desired product having a melting point of metalfoil)propionamide (compound N C-94, C-95).

2-amino-2,3-dimethylbutyramide (0.34 g, 3.0 mmol) and triethylamine (0.3 g, 3.0 mmol) dissolved in tetrahydrofuran (30 ml). When the mixture stirred at 10oC, thereto is added dropwise within 10 minutes add the chloride of 2-(4-triptoreline)propionic acid (0.7 g, 3.0 mmol). After completion of addition the reaction mixture is stirred for 3 hours at room temperature. The reaction mixture was concentrated and then add water to it. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 0.15 g (yield: 16%) of diastereoisomer A configuration (a configuration with a low polarity) having a melting point in the range from 121 to 124oC, and 0.3 g (yield: 32%) of diastereoisomer a configuration B configuration with high polarity) having a melting point in the range from 126 to 127oC.

Example of getting 13

Synthesis of 2-(4-chlorophenyl)-N-(1-cyanocyclohexyl)propionamide (compound N C-30).

1-amino-1-cyclopentanecarbonitrile (0.5 g, 5.0 mmol) and triethylamine (0.7 g, 7.0 mmol) dissolved in tetrahed henyl)propionic acid (1.0 g, 5.0 mmol). After completion of addition the reaction mixture is stirred for 7 hours at room temperature. The reaction mixture was concentrated and then add water to it. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer is dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 0.2 g (yield: 14%) of the desired product having a melting point in the range from 123 to 124oC.

Example of getting 14

Synthesis of 2-(3,4-dichlorophenyl)-N-(1-cyano-1,2-dimethylpropyl) propionamide (compound N C-169 C-170).

2-amino-2,3-dimethylbutyramide (0.5 g, 4.6 mmol) and triethylamine (and 0.46 g, 4.6 mmol) dissolved in tetrahydrofuran (30 ml). While stirring the mixture at 10oC thereto dropwise over 5 minutes add the chloride of 2-(3,4-dichlorophenyl)propionic acid (1.1 g, 4.6 mmol). After completion of addition the reaction mixture is stirred for 3 hours at room temperature. The reaction mixture was concentrated, then add water to it. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer was dried over anhydrous silica gel, what, therefore, leads to 0.19 g (yield: 27%) of diastereoisomer A configuration (a configuration with a low polarity) having a melting point in the range from 100 to 102oC, and 0.21 g (yield: 29%) of diastereoisomer a configuration B configuration with high polarity) having a melting point in the range from 171 to 173oC.

Example get 15

Synthesis of N-(1-isopropyl-1-methyl-2-oxopropyl)-2-(4 - triptoreline)propionamide (compound N D-97).

Hydrochloride 3-amino-3,4-dimethyl-2-pentanone (1.3 g, 7.8 mmol) and potassium carbonate (2.6 g, to 18.7 mmol) dissolved in acetonitrile (20 ml). When the mixture stirred at 10oC, thereto is added dropwise within 5 minutes add the chloride of 2-(4-triptoreline)propionic acid (1.9 g, 8.1 mmol). After completion of addition the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture was concentrated and then add water to it. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue was purified column chromatography on silica gel, thus, yield 1.7 g (yield; 65%) of the target product, it is arvanil)-N-(1-cyano-1,2-dimethylpropyl)propionamide (compound N C-33).

2-amino-2,3-dimethylbutyramide (2.6 g, 23.2 mmol) and potassium carbonate (3.3 grams, of 23.9 mmol) dissolved in acetonitrile (30 ml). When the mixture stirred at 10oC, thereto is added dropwise within 10 minutes add the chloride of 2-(4-chlorophenyl)propionic acid (4.5 g, of 22.2 mmol). After completion of addition the reaction mixture is stirred for 6 hours at room temperature. The reaction mixture was concentrated and then add water to it. The organic layer is extracted with ethyl acetate. After an ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate is removed under reduced pressure. The residue is purified liquid chromatography high pressure on a column of silica gel, thus, yields of 4.6 g (yield: 75%) of the desired product having a melting point in the range from 102 to 106oC.

Example of getting 17

Synthesis of N-(1-cyano-1,2-dimethylpropyl)-2-(3-phenoxyphenyl)ndimethylacetamide (compound A N-9). 3-phenoxyphenylacetic acid (0.9 g, 5.0 mmol) dissolved in chloroform (50 ml). Thereto at room temperature, add the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.2 g, 6.3 mmol) and the whole mixture is stirred for 20 minutes. To the mixture is added 2-amino-2,3-dimethylbutyramide the I reaction to the reaction mixture, water is added. The chloroform layer is washed with water and dried over anhydrous magnesium sulfate. The chloroform is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 1.2 g (yield: 72%) of the desired product having a melting point in the range from 136 to 137oC.

Example of getting 18

Synthesis of N-(1-cyano-1-dichlorodiethyl)-2-(4-chlorophenyl)ndimethylacetamide (connection N A-16).

4-chlorophenylalanine acid of 0.85 g, 5.0 mmol) dissolved in chloroform (50 ml). Thereto at room temperature, add the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.2 g, 6.3 mmol), and the whole mixture is stirred for 20 minutes. To the mixture is added 2-amino-2-dichlorocyclopentane (of 0.77 g, 5.0 mmol) and the reaction mixture is stirred for 10 hours at room temperature. After completion of the reaction, to the reaction mixture, water is added. The chloroform layer is washed with water and dried over anhydrous magnesium sulfate. The chloroform is removed under reduced pressure. The residue is purified column chromatography on silica gel, thus, yield 1.2 g (yield: 78%) of the desired product having a melting point in the range from 165 to 167oC.

1. Derivative generalk is;

R2means a hydrogen atom, a C1-C6alkyl group;

R3and R4each independently represents C1-C6alkyl group, a C2-C6alkenylphenol group, C3-C6cycloalkyl group, C2-C6CNS group or a C1-C4halogenating group, or R3and R4together with the carbon atom to which they are attached, form cycloalkyl group 5-7 membered cycle which may be substituted C1-C6alkyl group;

Q represents a cyano or a group of the formula-COR5where R5means a hydroxy-group, C1-C6alkyl group, a C1-C6alkoxygroup, an amino group, a C1-C6alkylamino or C1-C6dialkylamino;

X means a halogen atom, a C1-C6alkyl group, a C2-C6alkenylphenol group, C2-C6alkylamino group, C1-C4halogenating group, a hydroxy-group, C1-C6alkoxygroup, C3-C6cycloalkanes, C1-C4halogenlampe, alloctype, heterokaryosis selected from pyridyloxy, titilate, C1-C6alkylthio the C1-C6alkylamino, C1-C6dialkylamino, a nitrogroup, cyano, aryl group, heteroaryl group selected from pyridyl or pyrrolyl, alkylcarboxylic group, arylcarbamoyl group, taylorsville group;

each of Y and Z independently represents a hydrogen atom or a halogen atom;

n is an integer of 0-3, excluding the case when R3and R4are triptorelin group at the same time, and provided that when R1and R2both represent hydrogen, both Y and Z represent a hydrogen atom, and n represents an integer of 1-3.

2. Connection on p. 1, where R3and R4each independently represents C1-C6alkyl group, a C2-C6alkenylphenol group, C3-C6cycloalkyl group or a C1-C4halogenating group, or R3and R4together with the carbon atom to which they are attached, form cycloalkyl group 5-7 membered ring which may be substituted C1-C6alkyl group, X means a halogen atom, a C1-C6alkyl group, a C2-C6alkenylphenol group, C2-C6alkylamino group, C1-C4halogenating kruglosutochno, aryloxy, heterokaryosis selected from pyridyloxy, titilate, C1-C6allylthiourea, C1-C6alkylamino, C1-C6dialkylamino, a nitrogroup, cyano, aryl group, heteroaryl group selected from pyridyl or pyrrolyl, alkylcarboxylic group, arylcarbamoyl group, taylorsville group, excluding the case when R3and R4are triptorelin group at the same time, and provided that when R1and R2both represent hydrogen, both Y and Z represent a hydrogen atom, and n represents an integer of 1 to 3.

3. Connection on p. 1, where R3and R4each independently represents C1-C6alkyl group, a C2-C6alkenylphenol group, C3-C6cycloalkyl group or a C1-C4halogenating group, or R3and R4together with the carbon atom to which they are attached, form cycloalkyl group 5-7 membered cycle, X means a halogen atom, a C1-C6alkyl group, a C2-C6alkenylphenol group, C1-C4halogenating group, a hydroxy-group, C1-C6alkoxygroup, C1-C4halogenlampe, PU, C1-C6dialkylamino, a nitrogroup, cyano, aryl group, alkylcarboxylic group, arylcarbamoyl group, taylorsville group, excluding the case when R3and R4mean triptorelin group at the same time, and provided that when R1and R2both represent hydrogen, both Y and Z are hydrogen, and n is an integer of 1-3.

4. Connection on p. 1, where R3and R4each independently represents C1-C6alkyl group, a C2-C6alkenylphenol group, C3-C6cycloalkyl group or a C1-C4halogenating group, or R3and R4together with the carbon atom to which they are attached, form cycloalkyl group 5-7 membered cycle, X means a halogen atom, a C1-C6alkyl group, a C2-C6alkylamino group, C1-C4halogenating group, C1-C6alkoxygroup, C1-C4halogenlampe, fenoxaprop, C1-C6allylthiourea, C1-C6dialkylamino, a nitrogroup, cyano, phenyl group, alkylcarboxylic group or benzoyloxy group, Y and Z denote hydrogen, n is an integer of 1-3, except ..1, where R1is a hydrogen atom, R2, R3and R4each independently represents C1-C6alkyl group, a C2-C6alkenylphenol group, C3-C6cycloalkyl group or a C1-C4halogenating group, or R3and R4together with the carbon atom to which they are attached, form cycloalkyl group 5-7 membered cycle, Q denotes a cyano or a group of the formula-COR5where R5represents C1-C6alkoxy, C1-C6alkyl or amino group, X represents a halogen atom, a C1-C6alkyl group, a C2-C6alkylamino group, C1-C4halogenating group, C1-C6alkoxygroup, C1-C4halogenlampe, fenoxaprop, C1-C6allylthiourea, C1-C6dialkylamino, the nitro-group or phenyl group, Y and Z represent a hydrogen atom and n is an integer of 1-3, except when R3and R4are triptorelin group at a time.

6. Agricultural or horticultural fungicide comprising as an active ingredient derived phenylalaninamide specified in paras.1 to 4 or 5.

7. The way of gaining the acid, represented by formula 2

< / BR>
where R1, R2, X, Y, Z, and n have such values as defined in paragraph 1,

with an amine derivative represented by formula 3

< / BR>
where R3, R4and Q have the same meanings as defined in paragraph 1.

8. The method of obtaining derivatives of phenylalkylamine formula 1 under item 1, comprising a stage of interaction derived gelegenheid phenylalkanoic kivati represented by formula 4

< / BR>
where R1, R2, X, Y, Z, and n have such values as defined in paragraph 1;

L represents a halogen atom,

with an amine derivative represented by formula 3

< / BR>
where R3, R4and Q have the values as defined in paragraph 1.

 

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