TW397824B - Process for producing alkoxyiminoacetamide compounds - Google Patents

Description

Α6 Β6 V. Description of the invention () The present invention relates to the preparation of lanalkoxyimidoacetamide compounds, and particularly to an industrial method for preparing alkoxyimidoacetamide compounds used as agricultural pesticides. And the method and its new intermediate compound. To date, the present inventors have studied the development of agricultural pesticides for several years. As a result, it was found that the alkoxyimidoacetamide compound of the formula (I):

OR Α, ϊ Β Ν

Where A is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, cyclo (lower) alkyl, cyclo (lower) alkenyl, optionally substituted phenyl or alternatively substituted Heterocyclic group; B is -CHa-, -0-, -S-, -CH (0H>-, -CO-, diNR3- (where R3 is argon or lower alkyl), -CHaCHa- {Please first Read the notes on the back and fill out this page} Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs, -CH = CH- > ϋ · | ^ -C »C- * -CH.O-» -CHaS- »-CH , S (0)-,-OCHa-,-SCH ^^-SiCOCHa- or epoxy group; R is a lower alkyl group; R1 is Ra is a hydrogen or a lower alkyl group independent of each other; and pavement ~ represents E-iso Structure, any configuration of Z-isomers or mixtures of E- and Z-isomers; exhibits ability to control multiple pathogens of plants and rarely causes damage to useful plants such as cereals, vegetables, fruits, etc. ( See U.S. Patent No. 5,185,342 and JP-A No. 4-182461). The chemical structure of the alkoxyiminoacetamido compound (I>) is characterized by the conversion of the carboxylic acid group of the acetic acid unit adjacent to the benzene ring Optionally substituted carbamate Based on these characteristics, the compound (I > generally applies the Chinese National Standard (CNS) A4 specification (210X297 mm) to the paper size of the carboxylic acid unit) 3 A6 B6 V. Description of the invention () The carboxylic acid group is converted into a corresponding alkylalkoxyimine ethyl ester of a stuffed alkoxyyl group, which has a better sterilizing ability. The alkoxyimidoacetamide compound (I) KE- or Z-isomers exist. Generally speaking, E-isomers have better bactericidal ability than Z-isomers. The main object of the present invention is to provide the industrial production of alkoxyimidoacetamidamine Useful methods for compounds, especially methods for preparing E-isomers of high-purity alkoxyimidoacetamide compounds. Another object of the present invention is to provide new intermediate compounds for the above methods. These and other objects and advantages of the invention will be apparent to those skilled in the art from the narrative. As mentioned above, the present inventors have discovered alkoxyimidoacetamido compounds of the formula (1>), especially E -Isomers, used as agricultural pesticides It is of great value. Based on this development, the industrial method for preparing the compound has been studied. As a result, the present invention has been completed. That is, the present invention provides: (1) the preparation of an alkoxyiminoacetamidin compound of the formula (I); a way:

OR (Please read the precautions on the back before digging into this page}. Binding-Thread. Printed by the Ministry of Economic Affairs + Central Standards Bureau 8 Workers' Cooperative

A, \ B N

I where A is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy. The paper size is applicable to National Standard (CNS) A4 specifications (210X297 mm j 4) Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Preparation of A6 B6 V. Description of the invention () group, ring (lower) alkyl, ring (lower> alkenyl), optionally substituted phenyl or monocyclic optionally substituted heterocyclic group; BS-CHa- , -〇-,-S-,-CH (OH>-, -CO-, -NR3- (where R3 is hydrogen or lower alkyl), ~ CHaCHa_ > -CH = CH- »-C ^!-& Gt -CHaO- »-CHsS-» ~ CH2S (0)-, -DCHs-, -SCH2-, -S (0) CHa- or epoxy; R is lower alkyl; R1 and ... are independent hydrogens Or lower alkyl; and bonding ~ represents any configuration of E-isomers, isomers or mixtures of E- and Z-isomers; it includes compounds of halogenated formula U): (Please read the back (Please fill in this page for attention)

• Set each symbol as defined above to obtain a compound of formula (IV): OR COX where X is halogen and the other symbols are as defined above; react the compound of formula (IV) with an amine of formula HNR * Ra, Among them, ^ and {12 are as defined above; and optionally the compounds produced by acid treatment; the paper size and degree are applicable to China National Standard (CNS) A4 specifications (210x297 mm) _ 5-. Line

V. Description of the invention (A6 B6 hydrazone A method for preparing alkoxyimidoacetamidinium compound of formula (I):

CO-N, R2 where each symbol is as defined by ⑴, which includes a compound of formula (IV), where each symbol is as defined by ，, and the chemical formula: HNR1 amine, where each symbol is as defined by ， and acts ; And compounds produced by K-gallic acid treatment;

0X rv (3) A compound of chemical formula (1Π): (Please read the precautions on the back before filling in this page) Packing. Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

Where each symbol is as defined by chemical formula (I); 之 a method of preparing a compound of chemical formula <BI):

This paper size applies to China National Standard (CNS) A4 specifications (210x297 mm J

A B6 Five Ming explanation Mingfa

&quot; COOH

III where each symbol is as defined by chemical formula (I), which includes a compound of chemical formula U); where each symbol is as defined by chemical formula (I), and acts as a tritium; This page}

N. Binding. A compound of chemical formula (IV): thread.

OX

IV Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs where X is halogen and other symbols are as defined by chemical formula (I); and ⑻ a method for preparing compounds of chemical formula (IV): This paper scale applies Chinese National Standards (CNS) A 4 size (210x297 mm) 7 A6 B6

• B N

5. Description of the invention (

OR cox

IV where each symbol is as defined above, which includes the compound of the chemical formula (J [): {Please read the precautions on the back before filling this page>

printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, where each symbol is as defined by the chemical formula (I). The term "lower" used to define the chemical formula refers to no more than 8 carbon atoms, preferably no more than 6 Carbon atoms, preferably not more than 4 carbon atoms, unless otherwise specified. Examples of the lower alkyl group represented by KR, R1, Ra, R3 and A include those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Alkyl, for example, methyl, ethyl, propyl, isopropyl * butyl, isobutyl, t-butyl, etc. Examples of lower alkenyl represented by MA include those having 2 to 8 carbon atoms, Alkenyl groups of 3 to 6 carbon atoms are preferred, such as allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, hexenyl, hexadienyl and the like. Examples of lower alkynyl groups include 2 to 6 sulphur atoms. This paper size applies to China National Standard (CNS) A4 specifications (210x297 mm). 8 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. ___B6____ 5. Invention Explanation (), preferably 2 to 4 値 硪 alkynyl, for example, propargyl, ethyl Alkynyl, butyl, etc. Examples of lower alkoxy represented by A are alkoxy having 1 to 6 sulfonic atoms, preferably 1 to 4 carbon atoms, such as methoxy, ethoxy , Propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, etc. Examples of the cyclic (lower) alkyl group represented by M A include 3 to 8 A sulfonic atom, preferably a 3 to 6 sulfon atom, a cycloalkyl group such as cyclopropyl, cyclopentyl, cyclohexyl, etc. Examples of the cyclic (lower) alkenyl group represented by MA include 3 to 8 fluorene atoms Cycloalkenyl, preferably 5 to 7 carbon atoms, for example, cyclopentenyl, cyclohexyl, etc. The optionally substituted phenyl represented by KA includes unsubstituted phenyl and substituted phenyl. The optionally substituted fluorene ring group represented by KA includes an unsubstituted heterocyclic group and a substituted heterocyclic group. The unsubstituted heterocyclic group is, for example, a 5 to 6-angle heterocyclic group containing 1 to 3 Heteroatoms selected from the group consisting of oxygen, fluorene and hydrazone, which can form a fused ring system with carbocyclic or other heterocycles. Examples of unsubstituted heterocycles include pyrimidinyl, pyrimidinyl, pyrazinyl, thia Oxazolyl, benzoxazolyl, benzofuranyl, benzoxyl, oxazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, oxazolyl, quinolinyl, etc. MA means Examples of substituted phenyl or substituted heterocyclic groups include lower alkyl (e.g., methyl, ethyl * propyl, butyl, etc.), lower alkenyl (e.g., vinyl, allyl) Base, butenyl, etc., lower alkynyl t, please read the notes on the back before writing this page). Packing. Thread. This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) ) 9 A6 B6 printed by Shelley Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (eg, ethynyl, propargyl, butynyl, etc.), cycloalkyl (eg, cyclopropyl, cyclopentyl) , Cyclohexyl, etc.), cycloalkenyl (such as cyclopentenyl, cyclohexenyl, etc.), lower alkene (such as ethenyl, propynyl, isobutyridyl, etc.), lower alkylsilyl (Eg, methylsilyl, ethylsilyl, propylsilyl, butylsilyl, etc.), halogenated lower alkyl (eg trifluoromethyl Di (lower) alkylamino groups such as chloromethyl, 2-bromomethyl, 1,2-dichloropropyl (eg, dimethylamino, diethylamino, etc.), phenyl, phenyl (lower &gt; Alkyl (such as benzyl, phenethyl, etc.), phenyl (lower) alkenyl (such as styryl, cinnamyl, etc.), furanyl (lower) alkenyl (such as 3-furan vinyl, 2- Furan allyl, etc.), halogen (eg, fluorine, chlorine, bromine, iodine), nitro, cyano, -OR4 [where R4 is hydrogen, lower alkyl (eg methyl, ethyl, propyl, etc.), Lower alkenyl (eg, vinyl, allyl, butenyl, etc.), lower alkynyl (eg, ethynyl, 2-propynyl, 3-butynyl, etc.), lower alkynyl (eg acetamidine) Group, propynyl, butyryl, etc.), phenyl, lower alkoxyphenyl (eg, 3-methoxyphenyl, 4-ethoxyphenyl, etc.), nitrophenyl (eg, 3-nitrophenyl, 4-nitrophenyl, etc.), phenyl (lower) alkyl (eg, benzyl, phenethyl, phenylpropyl, etc.), fluorophenyl (lower) phenyl ( For example, 3-fluorenylphenylmethyl, 4-fluorophenylethyl, etc.), benzene Fluorenyl, tetrahydrofuran f, Bttpyridyl, trifluoromethylpyridyl, pyrimidinyl, benzoxazolyl, quinolinyl, benzamidine (lower) alkyl (eg, benzamidine Methyl, benzylethyl, etc.), phenylthiocarbenyl or lower alkyl phenylthiobenzyl (eg, tolylthiobenzyl, etc.)] and -CHa-Z-Re [wherein Z is -0-,- S-, or NRS (where [is is fluorene or lower alkyl), Re is phenyl, halogenated phenyl (eg, 2-chloro-phenyl, 4-gasified phenyl, etc.), lower alkoxyphenyl ( For example, 2-A paper size is in accordance with the Chinese National Standard (CNS) A 4 specification (210x297 mm) 10 ..........-... ......... 卞 ............. ,, ............ ........... install ......... order ......... ...... Line {Please read the precautions on the back before filling this page) A6 B6 Printed by the Order of the Ministry of Economic Affairs, the Central Bureau of Quasi-Bridge Consumer Cooperative, V. Description of the invention () Oxyphenyl, 4-ethoxybenzene Group, etc.), pyridine or pyrimidine]. The substituent of the phenyl or heterocyclic group represented by MA may be at any possible position on the ring and may be the same or different. The number of substituents is 1 to 5, more preferably 1 to 4, more preferably 1 to 3. Examples of the halogen represented by X include fluorine, chlorine, bromine, and iodine. In the method of the present invention, A is preferably an optionally substituted phenyl group such as an unsubstituted phenyl group or an M lower alkyl group and / or a halogen-substituted phenyl group; or an optionally substituted heterocyclic ring Such as unsubstituted pyridyl or M halogen and / or halogenated lower alkyl substituted pyridyl. B is preferably -0-, -CHa0- or -OCHa-. In the method of the present invention, A is preferably κ mono- or dimethyl and / or phenyl substituted with chlorine or fluorine (eg, 2-methylphenyl, 2,5-dimethylphenyl * 3, 5-dimethylphenyl, 3,4-dimethylphenyl, 4-fluorinated phenyl, 4-chlorophenyl, 2-methyl-4-chlorophenyl, etc.) or chlorine and / Or a pyridyl group optionally substituted by methyl trifluoride (eg, pyridyl, 2-hydropyridyl, 3, 5-dichloropyridyl, 2-trifluoromethylpyridyl, 3-trifluoride Methylpyridyl, 5-Trifluoromethylpyridyl, 2-Chloro-3-trifluoromethylpyridyl, 2-Ga-5-trifluoromethyl radical, 5-Ga_3_ Methylpyridinyl trifluoride, 3-pyridinyl-5-trifluoropyridyl, 6-pin-3-trifluoromethylpyridinyl, etc.). B is preferably -0- or -0CHa. R is preferably methyl. R1 is preferably hydrogen. R2 is preferably methyl. The compounds (I), (E), (III) and (IV) may be their E-isomers, Z-isomers, or a mixture of E- and Z-isomers. This is represented by a corrugated line (~) in the chemical formula. The compound (I) is preferably an E-isomer. (Please read the precautions on the back before filling in this page>. Loading. Thread. This paper size is applicable to China National Standard (CNS) A4 specification (210X297); ¢) Printed by A6, W Industry Consumer Cooperative, Central Bureau of Standards, Ministry of Economic Affairs B6_ 5. Description of the invention () Detailed examples of the desired alkoxyiminoacetamidinium compound (I) are described below (see US Patent No. 5,185,342 and JP-A 4-182461). Each of the following compounds Both include its (E) -isomers and (Z) -isomers, but (E) -isomers are preferred. N-methyl-2- [2- (2,5-dimethylphenoxy Methyl) phenyl] -2-methoxyiminoacetamide; 2- (2-phenoxyphenyl) -2-methoxyiminoacetamide; Ν, Ν-dimethyl 2- (2-phenoxyphenyl) -2-methoxyiminoacetamidoamine; N-methyl-2- (2-phenoxyphenyl) &gt; 2-methoxyimino Aminoacetamide; N-methyl-2- [2- (3-tolyloxy> phenyl] -2-methoxyiminoacetamide; N-methyl-2- [2- ( 4-nitrophenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (2-nitrophenoxy) phenyl] -2-methyl Oxyiminoacetamide; N-methyl-2- [2- (4-vinylphenylamino) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-chlorophenoxy) phenyl] -2- Methoxyiminoacetamidine; N-methyl-2- [2- (4-bromophenoxy) phenyl] -2-methoxyiminoacetamidine; N-methyl_ 2- [2- (4-1-butylphenoxy) phenyl] -2-methoxyiminoethyl ethyl amine; (Please read the precautions on the back before filling this page), Binding-thread.

This paper size applies to China National Standard (CNS) A4 specifications (210x297 Public Love J A6 B6 Printed by the Consumers' Cooperatives of the China Standards Bureau of the Ministry of Economic Affairs. 5. Description of the invention () N-methyl-2- [2- (4- Methoxyphenoxy) phenyl] -2-methoxyiminoacetamidoamine; methyl-2- [2- (4-trimethylsilylphenoxy) phenyl] -2- Methoxyiminoacetamidine; N-methyl-2- [2- (4-iodophenoxy) phenyl] -2-methoxyiminoacetamide; N-methyl-2 -[2- (4-chloro-3-methylphenoxy) phenyl] -2-methoxyiminoacetamidoamine; methyl-2- [2- (2-tolyloxy) phenyl ] -2-methoxyiminoacetamidoamine; N-methyl-2-[2-(4-tolyloxy) phenyl] -2-methoxymethoxyiminoethylamine; N-methyl 2--2- [2- (2,4-diisopropylbenzyloxy) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (4-iso Propylphenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3,4-dichlorophenoxy> phenyl] -2- Methoxyiminoethylamine; N-methyl-2- [2- (3-benzyloxyphenoxy) phenyl] -2-methoxyiminoacetamidine Amine; N-methyl-2- [2- (3-methoxyphenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3 -Phenoxyphenoxy) phenyl] -2-methoxyiminoacetamidine; {Please read the precautions on the back before filling out this page). The size of this paper applies to China National Standard (CNS). 4 Specifications (210 father 297 mm &gt; A6 B6 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs) 5. Description of the invention () N-methyl-2- [2- (4-phenoxyphenoxy> phenyl) ] -2-methoxyiminoacetamidine; N-methyl-2- [2- &lt; 2,4-dichloro-5-phenoxyphenoxy) phenyl] -2 -methoxy N-methyl-2-ethoxymethylamine; N-methyl-2- (2-τyloxyphenyl) -2-methoxyiminoacetamide I N-methyl-2- (2-phenoxy Methylmethylphenyl) -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3-phenoxyphenoxymethyl> phenyl] -2-methoxy Iminoacetamide; N-methyl-2- [2- (4-bromophenoxymethyl> phenyl] -2-methoxyiminoacetamide; N-methyl-2 -[2- (3-methoxyphenoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [ 2- (3_phenoxymethyl chloride> phenyl] -2-methoxyiminoacetaldehyde amine; N-methyl-2- [2- (2-chlorophenoxymethyl) Phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-styrylphenoxymethyl) phenyl] -2-methoxyimino Ethylamine; N-methyl-2- [2- (4-phenylfluorenylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- [ 2- (4_ Butylphenoxymethyl) benzyl] -2-methoxyiminoethyl ethylamine; (please read the precautions on the back before filling this page) * pack., Ϊ́τ _ line · This paper size is applicable to China National Standard (CNS) A4 specification (210 &gt; &lt; 297 gong). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 51 A6. B6 V. Description of the invention () N-methyl-2- [2 -(4-methylphenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-cyanophenoxymethyl) benzene Group] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (2,4-dichlorophenoxymethyl) phenyl] -2-methoxyimino Acetylamine; N-methyl-2- [2- (3,4-dichlorophenoxymethyl) phenyl] -2-methoxy Iminoacetamide; N-methyl-2- [2-3,5-dichlorophenoxymethyl) phenyl] -2-methoxyiminoacetamide; N-methyl -2- [2- (3-trifluoromethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; .N-methyl-2- [2- (3-di Methylaminophenoxymethyl) phenyl] -2-methoxyiminoethylamine; N-methyl-2- [2- (3 -desertized phenoxymethyl) phenyl]- 2 -methoxyiminoacetamidamine; N-methyl-2- [2- (3-nitrophenoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N -Methyl-2- [2- (4-fluorinated phenoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (3-iso Propoxyphenoxymethyl> phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-_gasified phenoxymethyl) phenyl]- 2-methoxyiminoacetamidamine; {Please read the precautions on the back before filling out this page) Packing-line. This paper size applies to China National Standard (CNS) A4 specification (210x297 mm) 15 A6 B6 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs V. Description of the invention () N-methyl-2- [2-phenylsulfur Methylphenyl) -2-methoxyiminoacetamidoamine; N-methyl-2- (2-phenyliminomethylphenyl). 2-methoxyiminoethyl Amidoamine; N-methyl-2- [2- (3-methyl-2-butenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [ 2- (3,7-dimethyl-2,6-butadienoxy) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (3, 3-dichloro-propenyloxy> phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (5-trifluoromethylpyridyl-2-yloxy 〉 Benyl] -2-methoxyiminoacetamidine; N-methyl-2- [2- (3-trifluoromethylpyridyl-2yloxy) benzyl] -2-methoxy Iminoacetamidoamine; N-methyl-2- [2- (5-trifluoromethylpyridyl-2yloxy) phenyl] -2-methoxyiminoethylamine; N -Methyl-2- [2- (2-pyrimidinyloxymethyl) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- [2- (2-pyridyloxy Methylmethyl> phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- (2-phenylthiophenyl) -2-methoxyiminoacetamidamine t N-methyl_2- [2- (3-hydroxyphenoxy) phenyl] -2-methoxyimine Acetylamine; {Please read the notes on the back before filling in this page). Binding. Binding. This paper size applies to China National Standard (CNS) A4 (210x297 mm) A6 B6 Central Bureau of Standards, Ministry of Economic Affairs Printed by the Industrial and Commercial Cooperatives 5. Description of the invention () N-methyl-2- [2- (3-tetrahydropyran-2-yloxyphenoxy) phenyl] -2-methoxyimino Acetylamine; N-methyl-2- [2- &lt; 3-pyrimidin-2-yloxyphenoxy) phenyl] -2-methoxyiminoacetamidine; N-methyl- 2- (2- [3-'(5-trifluoromethylpyridine-2-oxyphenoxy] phenyl} -2-methoxyiminoacetamidamine; methyl-2- {2- [3- (3-methoxyphenoxy) phenoxy] phenyl} -2-methoxyiminoacetamidoamine; N-methyl-2- (2- [3- (2-nitro Phenoxy) phenoxy] phenyl} -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3-quinolin-2-yloxyphenoxy) Phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (3-benzothiazol-2-yloxyphenoxy) phenyl] -2-methoxy Iminoacetamide; N-methyl-2- [2- (3-benzylidenemethyloxyphenoxy) phenyl] -2-methoxyimine Acetylamine; N-methyl-2- [2- (3-Toluenyloxyphenoxy) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- [2- (3-_Ethyloxyphenoxy) phenyl] -2-methoxyiminoacetamidinylamine; N-methyl-2- [2- (3-Bentyloxyphenoxy) Phenoxy> phenyl] -2-methoxylimidoacetamidamine; N-methyl-2- (2- [3- (2-fluorobenzyloxy) phenoxy] phenyl} -2-Methoxyimidoacetamidine; {Please read the precautions on the back before filling this page} .Packing.ΤΓ. Thread. This paper size applies to Chinese national standard (CNS &gt; T4 specification (210x297 mm) 17 A6 B6 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention () N-methyl-2- (2-([3- (2-propynyloxy) phenoxy] phenyl)- 2-methoxyiminoacetamidine; trimethyl-2- [2- <3-propvinyloxyphenoxy) phenyl] -2-methoxyiminoacetamido; N -Methyl-2- (2- [3- (2-furan-2-ylvinylphenoxy) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [ 2- (4-hydroxyphenoxy) phenyl] -2-methoxyiminoacetamide; N- Phenyl-2- [2- (4-benzyloxyphenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3- ¥ yloxy Phenylphenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3-phenylthiomethylphenoxy) phenyl] -2- Methoxyiminoacetamidine; methyl-2- {2- [3- (N-methylanilinomethyl) phenoxy] phenyl} -2-methoxyiminoacetamidine ; N-methyl-2- (2- [3- (2-pyridyloxymethylphenyl) -2-methoxyiminoacetamidamine; N-methyl-2- (2- [ 3- (phenylthiosulfenylmethyl) phenoxy] phenyl] -2-methoxyiminoethylamine; N-methyl-2- {2- [3- (pyrimidine-2- Methoxymethyl) phenoxy] phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- {2- C 3- (4-methoxyphenoxymethyl Phenoxy) phenyl] -2-methoxyiminoethylamine; n 篆 oxy] Fortunately installed ............ Order .............. line {Please read the precautions on the back before filling this page) This paper size applies to China National Standard (CHS) A4 specifications ( 210x297 mm) -18 A6 B6 Employees of the Central Standards Bureau of the Ministry of Economic Affairs Printed by Fei Cooperative 5. Description of the invention () N-methyl-2- {2- [3- (4-bromophenoxymethyl> phenoxy] phenyl} -2-methoxyimino · Acetylamine; N-methyl-2- [2- (3-phenoxymethylphenoxy) phenyl] -2-methoxyiminoacetamide; N-methyl-2- [2- (έ> -styrylphenyl) -2-methoxyiminoacetamidoamine; N-methyl-2- (2- (Z) -styrylphenyl) -2-methyl N-methyl-2- {2 '-[(1 "5'2" to) -1 ", 2" -epoxy-2 "-phenylethyl] phenyl } -2-methoxyiminoacetamidamine; N-methyl-2- (2'- [(1 ”11-, 2” 11 *)-1 ”, 2” -epoxy-2 ”- Phenylethyl] phenyl} -2-methoxyiminoacetamidoamine; N-methyl-2- [2-phenylethylphenyl] -2-methoxyiminoacetamidoamine ; N-methyl-2- [2- (ct-hydroxybenzyl) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- (2-benzylbenzylbenzene N-methyl-2- [2- (2-phenylphenoxymethyl) phenyl] -2-methoxyiminoacetamido ; N-methyl-2- [2- (3-phenylphenoxymethyl> benzyl] -2- N-methyl-2- [2- (4-phenylphenoxymethyl) phenyl] -2-methoxyiminoacetamide; (Please read first Note on the back page, please fill in this page again). Installation • ΤΓ-line. The silver standard of this paper is applicable to National Standard (CNS) A4 specification (210X297 mm) 19 A6 B6 Printed by the staff of the Central Procurement Bureau of the Ministry of Economic Affairs V. Description of the invention () N-methyl-2- [2- (2-isopropoxyphenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl- 2- [2- (4-isopropoxyphenoxymethyl) phenyl] -2-methoxyiminoacetamidine; methyl-2- {2- [2- (2-propyne Phenyloxy) phenoxymethyl] phenyl} -2-methoxyiminoacetamidoamine; N-methyl-2- {2- [3- (2-propynyloxy) phenoxy Methyl] phenyl) -2-methoxyiminoacetamidamine; N-methyl-2- (2- [4- (2-propynyloxy> phenoxymethyl] phenyl } -2-methoxyiminoacetamidoamine; N-dimethyl-2- [2- (4-trifluoromethylthiophenoxymethyl> phenyl] -2-methoxyoxy Aminoacetamidine; N-methyl-2- [2- (2-fluorophenoxymethyl) phenyl] -2- Oxyiminoacetamide; Ν, Ν-dimethyl-2- [2- (3-fluorinated phenoxymethyl) phenyl] -2-methoxyiminoacetamide; Ν -Methyl-2- [2- (2-trifluoromethylphenoxymethyl> phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (4 -Trifluoromethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine; methyl-2- [2- (2,3-dimethylphenoxymethyl) benzene Group] -2-methoxyiminoacetamidinylamine; N-methyl-2- [2- (2,4-dimethylphenoxymethyl) phenyl] -2-methoxyimine Ethylamine; Ν-methyl-2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine; {Please read the back first Note: Please fill in this page again.) Installation • ΤΓ.. Thread. This paper size applies to China National Standard (CNS) A4 specification (210X297 mm). Printed by A6 B6 of the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 5. Invention Explanation () N-methyl-2- [2- (2,6-dimethylphenoxymethyl> phenyl] -2-methoxyiminoacetamidamine; M-methyl-2- [2- (3,4-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine ; 'N-methyl-2- [2- (3, 5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [ 2-indomo-5-yloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (2,3-difluorophenoxy Methyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (2,5-difluorobenzyloxymethyl) phenyl] -2-methyl N-methyl-2- [2- (2,6-difluorophenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N -Methyl-2- [2- (3,4-difluorophenoxymethyl> phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- ( 3,5-difluorophenoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (2,3-dichlorophenoxymethyl) (Phenyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (2,5-difluorophenoxymethyl) phenyl] -2-methoxy Iminoacetamide; N-methyl-2- [2- (2,6-dichlorophenoxymethyl) phenyl] -2-methoxyiminoacetamide; (read first (Notes on the back, please fill out this page) National Standard (CNS) A4 Specification (210x297 mm) Printed by A6 B6, Consumer Cooperatives of Zhongli Standards Bureau, Ministry of Economic Affairs 5. Description of Invention () N-methyl-2- [2- (4_chloro-2- Methylphenoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (4-chloro-3-methylphenoxymethyl) benzene Group] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-chloro-3-ethylphenoxymethyl) phenyl] -2-methoxyimine Aminoacetamidine; N-methyl-2- [2- (3-chloro-5-methoxyphenoxymethyl) phenyl] -2-methoxyiminoacetamidine; methyl- 2- [2-2,3,5-trimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine; 1methyl-2- [2-2,3,6 -Trimethylphenoxymethyl) phenyl] -2-methoxyiminoethylamine; N-methyl-2- [2-2,4,6-trimethylphenoxymethyl ) Phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2-2,4,5-trifluorophenoxymethyl) phenyl] -2-methoxy Iminoacetamide; p-methyl-2- [2-2,4,6-trichlorophenoxymethyl) phenyl] -2-methoxyiminoacetamide; N-methyl-2 -[2-2,3,5-triaminated benzene Oxymethyl) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- [2-2,3,6-trichlorophenoxymethyl) phenyl]- 2-methoxyiminoacetamidine; methyl-2- [2- (4-chloro-3,5-dimethylphenoxymethyl) phenyl] -2-methoxyimino Acetamide; (Please read the precautions on the back before filling this page). Packing. The paper size of the thread applies to China National Standard (CNS) A4 specification (210x297 mm) 22 A6 B6 Employee Consumer Cooperatives, Central Standards Bureau, Ministry of Economic Affairs 5. Description of the invention () N-methyl-2- [2- (2-chloro-4,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine Amine; N-methyl-2- [2- (2,3,5,6-tetrafluorophenoxymethyl> phenyl] -2-methoxyiminoacetamidoamine; N-methyl -2- [2- (2,3,4,5,6-pentagas i: phenoxymethyl) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- [2- (3-chloro-5-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2 -(3,5-dichloropyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; methyl-2- [2- (6- Pyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (6-chloro-3-trifluoromethyl eftidine -2-yloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (6-chloro-5-trifluoromethylpyridine-2- Methoxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (2-benzoxazolyloxymethyl) phenyl] -2 -Methoxyiminoethylamine; N-methyl-2- [2- (2-benzothiazolyloxymethyl> phenyl] -2-methoxyiminoacetamidoamine; N -Methyl-2- [2- (7-hydroxyphenylpropenyloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (l -Naphthyloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; ............... .......... ^ ............................ ................. TΓ ............. .Line (Please read the notes on the back before filling in this page} This paper size uses the Chinese National Standard (CNS.) F 4 size (210x297 mm) — 23 — A6 B6 Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Fifth, the invention Ming () methyl-2- [2- (2-naphthyloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4- Chloro-1-naphthyloxymethyl) phenyl] -2-methoxyiminoacetamidine; methyl-2- [2- (6-bromo-2-naphthyloxymethyl) benzene Yl] -2-methoxyiminoacetamidamine; methyl-2- [2- (2-methyl-bonaphthyloxymethyl) phenyl] -2-methoxyiminoacetamidamine ; N-methyl-2- [2- (l-bromo-2-naphthyloxymethyl) phenyl] -2-methoxyiminoacetamidine; N-methyl-2- [2 -(3-allyloxyphenoxy) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (3-fluoromethoxyphenoxy ) Phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (3-trifluoromethylphenoxy) phenyl] -2-methoxyimino Acetylamine; N-methyl-2- [2- (4-fluorinated phenoxy> phenyl] -2-methoxyiminoacetamide; N-methyl-2- [2- ( 2,5-dimethylphenoxy) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-chloro-3-methylphenoxy> Phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (3,4-dimethyl (Oxy) phenyl] -2-methoxyiminoacetamidamine; {Please read the notes on the back before filling this page) This paper size is applicable to China National Standard (CNS) A4 specification (210x297 mm) 24 〇yi-Printed by A6 B6, Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention () N-methyl-2- [2- (3,5-dimethylphenoxy> phenyl] -2- Methoxyiminoethylamine; N-methyl-2- [2- (2,3-dimethylphenoxy) phenyl] -2-methoxyiminoacetamidoamine; N- Methyl-2- [2- (2,4-dimethylphenoxy) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (2,3 , 4-trimethylphenoxy) phenyl] -2-methoxyiminoethionamine; N-methyl-2- [2- (3,4,5_trimethylphenoxy) Phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (4-fluorinated phenoxymethyl) phenyl] -2-methoxyiminoethyl Amidoamine; N-methyl-2- [2- (2,4-difluorophenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (2-methylphenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- <3 -Methylphenoxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2- [2- (6-methoxypyridin-2-yloxymethyl) ) Phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (3, 6-dichloro-5-trifluoromethylpyridin-2-yloxymethyl ) Phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (5 ~ trifluoromethylpyridin-2-yloxymethyl> phenyl] -2- Methoxyiminoacetamidine; (Please read the notes on the back before filling out this page} This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) A6 B6 Employees of the Central Standards Bureau of the Ministry of Economic Affairs Printed by the cooperative V. Description of the invention () N-methyl-2- [2- (3-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidine Amine; N-methyl-2- [2- (6-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl- 2- [2- (5-chloro-3-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [ 2- (6-methylthiopyridin-2-yloxymethyl> phenyl] -2-methoxyimino Amidoamine; N-methyl-2- [2- (6-isopropoxypyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl -2- [2- (6-methoxy-3-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoethylamine; N-methyl- 2- [2- (6-methylthio-3-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; N-methyl- 2_ [2- (6-isopropoxy-3-trifluoromethylpyridin-2-yloxymethyl> phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2 -[2- (6-methoxy-5-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2- [2- (6-Isopropoxy-5-trifluoromethylpyridin-2-yloxymethyl &gt; phenyl] -2-methoxyiminoacetamidoamine; N-methyl-2 -[2- (6-methylthio-5-trifluoromethylpyridin-2-yloxymethyl) phenyl] -2-methoxyiminoacetamidamine; N-methyl-2 -[2- (2-Pyridine-3-yloxymethyl) phenyl] -2-methoxyiminoacetamidoamine; (Please read the precautions on the back before filling this page). .Tr. This paper size applies National Standard (CNS) A4 Specification (210x297 mm) Α6 Β6 Printed by the Consumer Cooperatives of the Central Procurement Bureau of the Ministry of Economic Affairs 5. Description of the Invention () In a preferred embodiment of the present invention, the compound (I) can be subjected to the following steps preparation. Step 1: Conversion of compound U) into compound (M). The compound (E) M is treated with M base in the first solvent to form salts of the compound U). Examples of the base include metal hydroxides or alkaline earth metal hydroxides (for example, sodium hydroxide, potassium hydroxide, etc., or alkaline earth metal sulfonates (such as sodium carbonate, potassium carbonate, or other alkaline metals or soil test). Metal alkoxides (eg, sodium methoxyl, sodium ethoxylate, potassium t-butoxy, etc.), etc. The amount of base used is generally 1 to 20 moles per mole of compound (I), preferably 1 to 3 moles. Examples of the solvent include N, N-dimethylformamide, dimethylimide, hydrocarbons (eg, toluene, benzene, xylene, cyclohexane, hexane, etc.), alcohol (E.g., methanol, ethanol, isopropanol, butanol, etc.), water, etc. These solvents can be used alone or as a mixture of K. The reaction temperature is generally 20 to 200D, preferably 50 to 180t. The reaction time is 5 to 100 hours, preferably 1 to 48 hours. The salt of the compound <M) thus obtained can be used in the next step as a reaction mixture or crude product, or after purification by a conventional method. Compound U) is isolated from the salts, e.g., the salts are optionally washed with an appropriate organic solvent After the impurities have been removed, the salts are treated with a suitable acid. Examples of the acid include halogen acids (e.g., hydrochloric acid, hydrobromic acid, etc.), sulfuric acid, sulfonic acids (e.g., trifluoromethanesulfonic acid, toluenesulfonic acid, etc.) and the like. Step 2 ·· Convert the compound (K &gt; to compound (ιν &gt;: &lt; Please read the precautions on the back before filling in this page). Binding. The size of the paper is based on China National Standards (CNS) A4 Specifications (210 father 297 male dragon ·) A6 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs __B6_ V. Description of the invention () Compound (B) in the presence or absence of a catalyst, in the absence of a solvent or in a suitable solvent The compound (IV) is produced by reacting with a halogenating agent. Examples of the halogenating agent include thionyl chloride, phosphine chloride, phosphorus pentachloride, phosphorus trichloride, sulfonium chloride, sulfur bromide, and phosphorus bromide. , Phosphorus pentabromide, phosphorus tribromide, ethylene difluoride, etc. The amount of halogenating agent is generally 1 to 10 ears per compound (®), preferably 1 to 3 ears, preferably slow. The halogenating agent is added because it can increase the amount of E-isomers. The catalyst is not necessarily used. When used, it can be appropriately selected from N, N-dimethyl-formamide, dimethylimide, hexamethylene Triamidine methyl sulfate, pyridine, triethylamine, iodine, zinc chloride, Vermeer reagent, etc. The amount of the chemical agent is generally 0.005 to 10 moles, preferably 0.01 to 1 mole per mole of the compound (M). The solvent is not necessarily used. When used, sulfohydrogen compounds (such as toluene, benzene, Xylene, hexane, cyclohexane, etc.), halogenated hydrocarbons (such as dichloromethane, dichloroethane, etc.) can be used alone or as a mixture thereof. The reaction temperature is generally -50 to 160 ° C, preferably The reaction time is usually from 0.2 to 48 hours, preferably from 0.5 to 24 hours. The compound (IV) thus obtained can be used in the next step as a reaction mixture or crude product, or purified by conventional methods. After that. Step 3: Conversion of compound (IV) to compound (I): Compound (IV) is produced by the action of an amine in the presence or absence of a test, in the absence of a solvent, or in a suitable solvent. Compound (I). This paper size applies the national standard (CNS) A4 specification (210X297 mm) 'ΓΓ- ............. .............. One ............ S ............ ..................................................... ..... {Please read the notes on the back before filling this page) A6 __B6_ V. Description of the Invention () Amine is a compound of the chemical formula: HNITR »(where R1 and R * are as defined above), and can be a primary amine, two Grade amine or ammonia. Examples of primary or secondary amines include lower alkylamines or di (lower) alkylamines, each of which has a lower alkyl group of R1 and Ra as described above. The amount of amine used is generally 1 to 20 moles per mole of compound (IV), preferably 1 to 5 moles. Tests can be used to neutralize the acid produced. Alternatively, the amidine may be replaced with an excess of the above-mentioned amine. When used, it may be selected from pyridine, triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, t-butoxide and the like. The amount of alkali used is generally 1 to 20 moles, preferably 1 to 3 moles per compound of the humor. When a solvent is used, it may be appropriately selected from hydrocarbons (eg, toluene, benzene, xylene, cyclohexane, hexane, etc.), halogenated hydrogen-breaking compounds (eg, dichloromethane, dichloroethane #), Ethers (such as tetrahydrofuran, dioxane, etc.), water, etc. These solvents can be used alone or in mixtures. When the above amines or bases are liquid mashes, they can also be used as solvents. The reaction temperature is generally -50. To 16〇υ, preferably 0 to 120t :. The reaction time is generally 0.1 to 24 hours, preferably 0.5 to 12 hours. Printed by the Shellfish Consumer Cooperative of the Sample Procurement Bureau of the Ministry of Economic Affairs {Please read the precautions on the back before (Filling page) Filling the line The alkoxyiminoacetamidinium compound (I) thus obtained is generally a mixture of E- and Z-isomers. This mixture can be used as an agricultural fungicide. Because in general E-isomers are stronger than Z-isomers, it is preferable to increase the content of E-isomers. In general, the isomerization of the Z-isomer to the E-isomer is carried out under acidic conditions. This type of isomerization will occur to some extent in any of the above steps under acidic conditions. However, if exposed, the compound (I) prepared in the last step can be optionally treated with acid to increase the E-isomerization by M isomerization. This paper is applicable to the Chinese National Standard (CNS) A4 specification (210X297). (%) A6 B6___ 5. Description of the invention () Content of the substance. In a preferred embodiment of the present invention, the processing is performed. If necessary, the compound (I) can be isolated and purified from the reaction mixture before isomerization. The compound (I) can be isomerized by treating the compound (I) with an M acid in a suitable solvent. Examples of the acid include hydrohalic acids (e.g., hydrochloric acid, hydrobromic acid, etc.). Hydrogen halide (eg, hydrogen gas, hydrogen bromide, etc.), sulfonic acid (eg, toluene sulfonic acid, etc.), thionyl chloride, ethylene dichloride, aluminum chloride, aluminum bromide, titanium trichloride, four Titanium chloride, etc. These acids may be used singly or as a mixture thereof. The amount of the acid is generally 0.001 to 20 acetic acid per urinary compound, preferably 0.01 to 2 acetic acid. Examples of the solvent include sulfonium compounds (such as benzene, toluene &gt; xylene), carbon halide Hydrogen compounds (such as dichloromethane, 1,2-dichloroethane, etc.), ethers (such as tetrahydrofuran, dioxane, etc.), and ketones (such as acetone, ethyl methyl ketone, etc.). Among them, preferred These are hydrocarbons (eg, benzene, etc.) and halogenated sulfonated hydrogen compounds (eg, dichloromethane, 1,2-digasethane, etc.) The reaction temperature is generally 0 to 150C, preferably 20 to 110. The reaction time is generally 0.5 to 72 hours, preferably 1 to 24 hours. The compound used as the starting material in the first step (1) can be prepared according to the method described in Japanese Patent Application No. 5-273556. For example, The compound (Π) in which B is -〇CHa- can be prepared according to the following procedure. {Please read the precautions on the back before filling this page). Binding. Binding-line · Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs This paper size is applicable to China National Standard (CNS) A4 specification (210x297 mm) Ming （） A-OH (V) +

X (VI)

(VII)

0H

CN A6 B6 (Please read the precautions on the back before filling this page)-Install CN (VIII) (IX). Order... Printed by the Consumers' Cooperative of the China Standards Bureau of the Ministry of Economic Affairs.

ΙΓ This paper size applies to China National Standard (CNS) A4 (210x297 mm) A6 B6 5. Description of the invention () First, in a suitable solvent, in the presence of a base and in the presence or absence of a phase transfer catalyst , Compound excess α, α'-0-dihalogenated xylene (VI) is reacted. Examples of usable ot, α dihalogenated xylenes (VI> include α, α '-0-dichloroxylene., Ot, ot | Dibromoxylene, ot, ct'-0-diiodized Xylene, etc. The amount of α, α dihalogenated xylene is 1 to 10 ears, preferably 3 to 5 ears per mole of compound (V). When this reaction is performed without using an excessive amount of α, α ′ -0- When dihalogenated xylene (VI), a large number of chemical formulas are formed: (Please read the precautions on the back before filling this page)

-A compound of which each symbol is as defined above. Examples of the solvent used include the same solvents described in the above reaction using an alkali metal amide. These solvents can be used alone or in combination. Examples of the base used include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, potassium t-butoxide and the like. The base is used in an amount of 1 to 5 and preferably 1 to 2 per stilbene compound (ν>). Examples of the phase transfer catalyst include the same phase transfer catalyst described in the above-mentioned reaction using ageing fluoride. The amount of the phase transfer catalyst is 0.01 to 0.2 moles per mole compound (V), preferably 0.05 to 0.1 moles. The reaction temperature is 0 to 1201, preferably 20 to 100 ° C. The reaction time is 20 minutes to 12 hours, preferably 30 minutes to 3 hours. The remaining α. Α '-0-dihalogenated xylene (VI) is obtained from the crude benzine. The paper size is in accordance with Chinese National Standard (CNS) A4 (210x297 mm). ). Line. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Α6 Β6 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention () Removed from the basic halogen (VH). The residue can be directly or through traditional After purification, the method is used in the next step. Then, in an appropriate solvent, in the presence or absence of a phase transfer catalyst, benzyl teeth and an alkali metal atmosphere are used to obtain benzyl cyanide (VI). Alkali metal vapor Examples include sodium cyanide, potassium fluoride, etc. The amount of rhenium metal odorant used is benzyl halide per ear (V0 &gt; 1 to 5 moles, preferably 1 to 2 moles. Examples of solvents used include acetone , Ethyl, methyl ethyl ketone, dimethyl formamide (DMF), dimethyl methylene (DMSO), toluene, methanol, ethanol, isopropanol, butanol, tetrahydrofuran (THF), dioxane , Water, etc. These solvents can be used alone or in combination. Examples of the phase transfer catalyst include special-η-butylammonium chloride, special-n-butylammonium bromide, and -η-hydrogenbutylammonium sulfate, Tert-methylammonium bromide, benzyltriethylammonium chloride, tris (3, 6-dioxeptyl) amine, etc. The amount of this phase transfer catalyst is 0.01 to per benzyl halide (VB). 0.2 ears, preferably 0.05 to 0.1 mole. The reaction temperature is 0 to 120C, preferably 20 to 100TC. The reaction time is 10 minutes to 24 hours, preferably 30 minutes to 5 hours. The benzylfluorene thus obtained Compound (VI) can be used in the next step as a reaction mixture, or the crude product * or after purification by conventional methods. Then, in a suitable solvent, in the presence of a base In the presence or absence of a phase transfer catalyst, the above-mentioned benzyl halide (υι) and alkyl nitrite react with each other to form amidine to obtain α-hydroxyiminobenzyl chloride {Please read the note on the back first Please fill in this page for matters). Binding. Binding. Threads. This paper size is applicable to China National Standard (CNS) A4 specifications (210 fathers 297 mm). Printed by A6 B6 by the Bayer Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. Note () (K) ° Examples of alkyl nitrites used include methyl nitrite, ethyl nitrite, propyl nitrite, isopropyl nitrite, butyl nitrite, isoamyl nitrite, and the like. The alkyl nitrite is used in an amount of 1 to 5 moles per benzyl halide (VI), preferably 2 moles per ridge. Examples of the solvent used include the same solvents described in the above reaction using rhenium metal fluoride. These solvents can be used alone or in combination. Examples of the tests used include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium sulfonate, sodium methoxide, sodium ethoxide, sodium fluoren-butoxide and the like. The amount of base used is 1 to 5 moles, preferably 1 to 2 moles per benzyl argon (VI). Examples of the phase transfer catalyst include the same phase transfer catalyst described in the above reaction using an alkali metal cyanide. The amount of the phase transfer catalyst is 0.01 to 0.2 mole per benzyl cyanide (VI) per ear, preferably 0.05 to 0.1 mole. The reaction temperature is 0 to 120¾, preferably 20 to 501. The reaction time is 5 minutes to 12 hours, preferably 30 minutes to 3 hours. The α-hydroxyiminobenzyl fluoride (K>) thus obtained can be used in the next step as the reaction mixture, crude product, or after purification by conventional methods. Then, in a suitable solvent, in the presence of a base In the presence or absence of a phase transfer catalyst, the α-hydroxyiminofluorenyl cyanide (IX) and an alkylating agent are reacted to obtain α-alkoxyiminobenzyl fluoride (I Ί. Examples of the alkylating agent used include dialkyl sulfate (eg, disulfate &lt; please read the notes on the back before filling out this page). Binding:-The size of the paper is applicable to the Chinese National Standard (CNS) A 4 Specifications (210x297) «Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A6 ____B6_ V. Description of the invention () Methyl esters, etc.), Alkyl halides (eg, methyl chloride, methyl bromide, methyl iodide, etc.) Etc. The amount of the alkylating agent used is 1 to 5 ears, preferably 1 to 2 ears per mole of α-hydroxyiminobenzyl fluoride (IX). Examples of the base used include sodium hydroxide, hydroxide Potassium, sodium estrogen, potassium estroate, sodium methoxide, sodium ethoxide, special -Potassium butoxide, etc. The amount of the base used is 1 to 5 ears, preferably 1 to 2 ears per mole of ct-hydroxyiminobenzylidene (IX). Examples of solvents used include and are described in The same solvents in the above-mentioned reaction using an alkali metal fluoride. These solvents may be used alone or in combination. Examples of the phase transfer catalyst include the same phase transfer catalyst as described in the above-mentioned reaction using an alkali metal halide. This phase The amount of the transfer catalyst is 0.01 to 0.2 ears, preferably 0.05 to 0.1 ears per α-hydroxyiminobenzyl halide (IX) of the ear. The reaction temperature is 0 to 120t :, preferably 0 to 30t! The reaction time is 5 minutes to 12 hours, preferably 15 minutes to 2 hours. In addition, under the same conditions as the conversion of compound (VI) to compound (K), benzyl cyanide (VI) and a nitroso Alkyl ester reaction. Then, an alkylating agent M is added to the reaction mixture for alkylation. Therefore, the α-alkoxyiminobenzyl fluoride (Π ′> can be obtained by the synthesis of a single furnace. Α obtained in this way -Alkoxyimino benzyl fluoride can be used in the next step as It is a reaction mixture, or a crude product, or after being purified in a conventional manner. The alkoxyliminyl ethyl amine (I) prepared by the method of the present invention can be used as an agricultural paper. The Chinese national standard (CNS) A4 is applicable. Specifications (210X297 mm) (Please read the notes on the back before filling in this page). Binding. Printed by A6 B6, Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs 5. Description of Invention () Industry fungicides, for example, as described in The method of U.S. Patent No. 5,185,342. As described above, according to the present invention, a method for preparing an alkoxyiminoacetamido compound (I) is provided. This method produces the compound in a high yield. Further, because The desired compound in the final product, especially its E-isomer, has a high content, and the compound is easy to purify and has excellent bactericidal ability. The following examples illustrate the invention in further detail, but should not be construed as limiting it. Example 1 Synthesis of 2- (2,5-dimethylphenoxymethyl) benzyl chloride (175.06 g, 1.0 mole) and acetone (200 ml) were added to 2,5-xylenol (24.43 g, 0.2 mole). The mixture was heated under reflux for 8 hours. After the reaction was completed, the resulting product was removed Insoluble matter, excess α, α'-0-dichloroxylene is evaporated under reduced pressure to obtain 2- (2,5-dimethylphenoxymethyl) benzyl gaseous as a colorless oil (53.20 g, yield: 88.5%, purity: 86.8%). Example 2 Synthesis of 2- (2,5-dimethylphenoxymethyl) benzyl chloride 95% sodium hydroxide (13.89 g , 0.33 gel ear) and water (60 ml) were added to 2,5-xylenol (36.65 g, 0.3 mole), and dissolved under heating. Then the water was evaporated under reduced pressure. Α, α dichloride Xylene (105.04 g, 0.6 mol) and acetone (150 ml) were heated to the sodium salt produced, and the mixture was heated under reflux for 1 hour. After the reaction was completed, this paper was removed and the Chinese standard (CNS &gt; A4 regulations (210x297 mm) {Please read the precautions on the back before filling this page). Binding. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs and printed by A6 __B6_ V. Inventive matter () The insoluble matter produced. After steaming, the colorless crystals were obtained as 2- (2,5-dimethylphenoxymethyl> benzyl chloride (39.07 g, yield: 49.9%). Bp 145-147eC / 0.6 mmHg, mp 46.5-48.5 ° C. ^ -NMR (CDC13) δ ppm: 2.21 (s / 3H), 2.34 (s, 3H), 4.74 (s, 2H), 6.71-7.54 (m, 7H). Di 3 Synthesis 2 -(2,5-Dimethylphenoxymethyl) benzyl gaseous compound is added to 2- (2,5-dimethylphenoxymethyl) benzyl chloride (purity: 86.8%, 1.50 g, 5IIB101) ), 95% sodium amide (0.31 g, 6 mo1), vaporized triethylbenzyl ammonium (0.06 g, 0.25 mmol), acetone (4 ml> and water (2 ml). The mixture was heated under rolling for 5 minutes. Hours. After the reaction was completed, water (100 ml) was added. The resulting mixture was extracted with diethyl ether (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated by a silica gel layer method (Ethyl acetate / η-hexane ) Purified to obtain 2- (2,5-dimethylphenoxymethyl) benzyl odorant (1.23 g, yield: 97 articles). Mp 51.5-53 ° C. ^ -NMRCCDClj) 5 ppm: 2.18 (s, 3H), 2.34 (s, 3H), 3.89 (s, 2H), 5.05 (s, 2H), 6.72-7.52 (m, 7H). The fourth example synthesizes 2- (2, 5-dimethyl) Phenoxymethyl> -ct-hydroxyiminobenzyl nitride will be 85% potassium hydroxide (0.40 g, 6 μοΠ, toluene (5 ml) and this paper is a common Chinese National Standard (CNS) A 4 Specifications (210X297 mm) ............ ... (............ ".................. install ... .............. Order .............. line (Please read the notes on the back before filling in this page> Α6 Β6 Printed by the Ministry of Economic Affairs and the Central Bureau of Quasi-Bureau Shellfish Consumer Cooperatives 5. Description of the invention () Butyl nitrite (0.62 g, 6 mmol &gt; added to 2- (2,5-dimethylphenoxymethyl) Benzyl fluoride (1.26 party, 5 mmol). The mixture was searched at room temperature for 8 hours. After the reaction was completed, water (100 ml) was added. It was neutralized with hydrochloric acid, extracted with ethyl acetate (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue M was separated and purified on a silica gel layer (ethyl acetate / η-hexane) to obtain 2- (2,5-dimethylphenoxymethyl ία-hydroxyiminobenzyl odorant ( 1. 30 g, yield: 92.8%, E / Z = 15/85). Take a part of it and separate E-isomer and Z-isomer, and determine its physical properties: E-isomer : -Mp 114-115 ° C. W-NMR (CDC13) δ ppm: 2.23 (s, 3H), 2.31 (s, 3H), 5.06 (s, 2H), 6.65-7.66 (m / 7H), 8.41 (s / lH). Z-isomer: mp 150.5-151.5 ° C. W-NMR (CDC13) δ ppm: 2.24 (s, 3H), 2.31 (s, 3H), 5.24 (s, 2H) / 6.64-7.79 (m / 7H), 8.68 (s, lH). Example B to synthesize 2- (2, 5-dimethylphenoxymethyl) -α-methoxyiminobenzyl fluoride Potassium acid (3.32 g, 0.024111111〇1) and acetone (200 ml) were added to 2- (2.5-dimethylphenoxymethyl-hydroxyiminobenzyl fluoride (£ / 2 = 15/85). (5.61g, 0.02 | »111〇1>. Search and mix the mixture for 5 hours {Please read the precautions on the back before filling in this page). Binding. Binding This paper size applies to China National Standard (CNS) A4 specifications (210 father 297 public love) A6 B6 Central Standard of the Ministry of Economic Affairs When printed by the staff consumer cooperative V. Invention Description (), then dimethyl gallate (3.03 g, 0.024 uieol) was added, and the mixture was stirred at room temperature for 18 hours. After the reaction was completed, the insoluble matter produced was removed. To the residue obtained after evaporation under reduced pressure, toluene (50 ml) and a 1 N aqueous sodium hydroxide solution (50 ml) were added. The mixture was stirred for 1 hour. After stirring, water (150 ml) was added. The mixture was diethyl ether ( 150 ml), extracted with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel layer separation (ethyl acetate / η-hexane) to obtain 2- (2, 5-di Methylphenoxymethyl) -cx-methoxyiminobenzyl fluoride (5.44 g., Yield: 92.4%, E / Z = 15/85). Take a part of it and change E- Separate isomers and Z-isomers, and determine their physical properties. E-isomers: colorless oil. H-NMR (CDC13) δ ppm: 2.23 (s, 3H), 2.31 (s, 3H), 4.04 (s, 3H), 5.01 (s, 2H), 6.63-7.63 (m, 7H). Z-isomer: colorless crystals. mp 107-108 ° C. ^ -NMR (CDC13) 6 ppm: 2.24 (s, 3H), 2.30 (s / 3H), 4.13 (s, 2H), 5.26 (s, 2H), 6.62-7.76 (m, 7H). 'Example of synthesis of 2- (2,5-dimethylphenoxymethyl> -α-methoxyiminobenzyl cyanide will be 95% sodium hydroxide (0.32 g, 7.5 mmol), Acetone (5 ml) and nitrosylbutyl nitrate (0.62 g, 6 min) were added to 2- (2,5-dimethylbenzyloxy) benzyl fluoride (1.26 g, 5 μm βο1). In the chamber Stir the mixture warmly (please read the precautions on the back before filling in this page). Binding ... The size of the threaded paper applies to the Chinese national standard (CNS &gt; A4 specification (210X297 mm &gt; A6 B6) Staff consumption of the Central Standards Bureau of the Ministry of Economic Affairs Cooperative print 5. Description of invention () 2 hours. Add dimethyl sulfate (0.95 g, 7.5ππιο1), stir the mixture under ice cooling for 10 minutes and stir at room temperature for 1 hour. After the reaction is completed, add toluene (10 ml) and 1N aqueous sodium hydroxide solution (10 ml), stir the mixture for 1 hour at room temperature. After stirring, add water (100 ml>). The mixture is extracted with ether (100 ml), anhydrous sulfur The magnesium acid was dried and concentrated under reduced pressure. The resulting residue was purified by silica gel layer separation (ethyl acetate / η-hexane) to obtain 2- (2,5-dimethylphenoxy). Methyl) -α-methoxyiminobenzyl odorant (1.29 g, yield: 87.6%, E / Z = 13/87). 筮 Seven cases of synthesis (Z) -2- [2- (2,5 -Dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetic acid. 85% potassium hydroxide (0.26 g, 4πηπο1 &gt;, butanol (4 ml) and water (0.4 ml) were added. To (2) -2- (2,5-dimethylphenoxymethylmethoxyiminobenzyl halide (0.59 g, 2 mmol). The mixture was stirred under reflux for 7 hours. After the reaction was completed, added Water (100 ml). The pH value of the resulting mixture was adjusted to no more than 3 by adding 6N aqueous hydrochloric acid solution *, and extracted twice with methylene chloride (50 ml), dried over anhydrous magnesium sulfate, and Concentrated under reduced pressure to obtain crystals (0.60 g &gt;, and then recrystallized from η-hexane to obtain U) -2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2 -Methoxyiminoacetic acid (0.42 g, yield: 67.0%). Mp: 112.5-113.5 ° C ^ -NMR (CDC13 ) δ ppm: 2.21 (3H, s), 2.29 (3H, S), 2.65 (lH, brs), 4.09 (3H, s), 5.20 (2H, s), 6.64-7.63 (7H, n〇. flutes Example Synthesis of 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetic acid {Please read the precautions on the back before filling this page}. 装 * ^ 1: Line. This paper size is in accordance with China National Standard (CNS) A4 specification (210X297 mm) 5. Invention Description (A6 B6 Printed on 2- (2,5-A) Phenylphenoxymethyl)-. Α-methoxyiminobenzyl halide 邙 / 2 = 13/87) (2.94 g, 10111111) was added with 96.7% potassium argon oxide (1.16 g, 2 (Bmol), butanol (20 ml) and water (2 ml). The mixture was stirred under rolling for 13 hours. After completion, 1N hydrochloric acid aqueous solution (150 ml) was added. The mixture was extracted with benzene (150 ml), washed with water (100 ml), and dried over anhydrous magnesium acetate. And concentrated under reduced pressure to obtain crude 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetic acid (2.99 g, yield 95.5%, Z = At least 99%). 例 9 cases of synthesis of 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyimine-N-methylacetamide. Toluene ( 10 ml>, thionyl chloride (1.36 g, 11 mmol) and dimethylformamide (0 fu?) (0.1 ml) were added to the crude 2- [2- (2,5-dimethylphenoxymethyl) (Phenyl) phenyl] -2-methoxyiminoacetic acid (Z = at least 99%) (2.99 g, 9.5 μο1), and the mixture was stirred at 70¾ for 1.5 hours. After completion of the reaction, the mixture was concentrated to obtain [2 -(2,5-dimethylphenoxymethyl) phenyl] -2-methoxyimino @ chloro 邝 / 2 = 75/25). ^ -NMR (CDC13) δ ppm: 2 · 18 ( 2.25H, s), 2.27 (0.75H / s), 2.29 (2.25H, s), 2.32 (0.75H, s), 4.04 (0.75H, s) 4.12 (2.25H / s) / 4.88 (1.5H, s), 5.26 (Ο.5H, s), 6.6 7-7.57 (7H, m) The resulting crude product was dissolved in dry toluene (10 liters) * The solution was added dropwise to a 40% methylamine aqueous solution (2 · In a suspension of 96 g of Mmaol) and toluene (10 ml), stir the mixture at room temperature for 2 hours. After the reaction is complete, add water (100 ml). {Please read the precautions on the back before filling this page) .Binding-binding. -The size of the paper is applicable to China National Standard (CNS) A4 specification (210X297 mm). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. A6 B6. 5. Description of the invention () By adding 6N hydrogen The pH of the resulting mixture was adjusted to no more than 3 with aqueous chloric acid solution, extracted with diethyl ether (150 ml>, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was separated on a silica gel layer (ethyl acetate / η-hexane> purification to give 2- [2- (2,5-dimethylphenoxymethyl> phenyl] -2-methoxyiminoamidoacetamidamine (2.64 g, yield: 84.8 % * Ε / Z = 75/25). 10th synthesis 邙) -2- [2- (2,5-dimethylphenoxymethyl &gt; phenyl] -2-methoxyimino-N -A Acetylamine adds toluene (3 ml) and concentrated hydrochloric acid (0.61 g, 6Πβκ) 1> to 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2- Methimido-N-methylacetamide (0.98 g, E / Z = 75/25), and the mixture was stirred at 80T: for 2 hours. After the reaction was completed, water (150 ml) was added. This mixture was extracted twice with methylene chloride (50 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crystals (1.01 g, E / Z = 95/5). The crystals were produced by recrystallization from toluene. (E) -2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyimino-N-methylethylamine (0.72 g, yield 71.5%). Mp: 136-1370C. W-NMR (CDC13) δ ppm: 2.18 (3H, s), 2.29 (3H, s), 2.88 (3H, d / J = 4.9Hz), 3.95 (3H, s ), 4.92 (2H, s), 6.62-7.57 (8H, m) ... 11th Example Synthesis of 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-form Oxygen (please read the notes on the back before filling this page). Packing. The paper size of the paper is applicable to China National Standard (CNS) A4 (210X297 mm). Printed by A6 _______B6 _ 5. Description of the invention () Iminodiacetic acid in 2- (2,5-dimethylphenoxymethyl) -α-methoxyiminobenzyl fluoride (E / Z = 13/87> ( 2.94 g, 10 amol) was added with 96.7% potassium hydroxide (1.16 g, 20 mmol) and a solvent shown in Table 1. The mixture was shown in Table 1 The reaction was carried out under the conditions shown in the table. After the reaction was completed, a 1N aqueous hydrochloric acid solution (150 ml) was added. The mixture was extracted with toluene (150 ml), washed with water (100 ml), dried over anhydrous magnesium sulfate, and reduced in water. It was concentrated under reduced pressure to give crude 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetic acid. The crude product was analyzed by HPLC to calculate the yield. 1 Table • Example Solvents (Liter / Mill Ear) Reaction Conditions Yield (%) Emb Example 11 PhMe (2.0) / MeOH (0.2) reflux, 13 hours 52 59/41 12 PhMe (2.0) / H20 (0.2) / MeOH ( 0.2) reflux, 20 from time to time 76 26/74 13 MeOH (1.0) / H20 (0.5) reflux, 22 hours' (internal temperature: 740 90 10/90 14 PhMe (0.3) / H20 (0.5) / MeOH (0.7) Reflux, 21 hours (internal temperature: 74υ) 93 24/76 Flute 15 cases Synthesis of 2- [2- (2,5-dimethylphenoxymethyl> phenyl] methoxyimino-N-methyl Ethylamine is applicable to Chinese National Standard (CNS) A4 specifications (210〆297). ............. .......................................... ..................................... ..... 玎 .............. line (Please read the notes on the back before filling this page)

Printed by A6 B6, Shellfish Consumer Cooperative, Central Bureau of Standards, Ministry of Economic Affairs 5. Description of the invention () The 2- [2- (2,5-dimethylphenoxymethyl> phenyl] -2-methoxyimino group Acetic acid (9.4g, 30β · ο1, E / Z = 20/80) was dissolved in dimethylformyl limb (DMF> (0.11g, 1.5mmol) and toluene (20ml). K for 5 hours at 60 &lt; 〇 95% of a solution of thionyl chloride (4.13 g, 33111111101) and toluene (10 ml) were added dropwise. The mixture was stirred at 60¾ for 5 hours. After the reaction was completed, the mixture was concentrated under reduced pressure. To a total of 30 grams, yielding crude 2- [2- (2.5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidine chloride. One and a half of the resulting crude product From 20 to 25Ό, dropwise into a suspension of 40% methylamine aqueous solution (2.8 g, 36.1 mmol), water (10 g) and toluene (10 g) over 1 hour. The other half of the crude product and 28.8% hydrogen Aqueous potassium oxide solution (4.2 g, 30 mmol) was added separately and simultaneously at 20 to 25 t for 1 hour. The mixture was stirred at 20 to 25 t for 1.5 hours. After the reaction was completed, the solution was added by adding 1 N aqueous hydrogen acid solution (10 ml). The mixture was acidified and extracted with ethyl acetate (100 ml). The saturated layer of ethyl acetate was washed twice with saturated brine (150 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield 2- [2- ( Crystals of 2,5-dimethylphenoxymethyl) phenyl] -2-methoxyimino-N-methylacetamide (purity: 95.4%, determined by HPLC analysis) (9.81 g, pure Yield of product: 95.6%, E / Z = 93/7) 16 cases of isomerization 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyoxy Aminoacetamidine, toluene (5 ml) and thionyl chloride (0.12 g, added to 2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxy The paper size of imine acetam is applicable to China National Standard (CNS) A4 specification (210x297 mm) -44-{Please read the precautions on the back before filling out this page). A6 B6__ printed by the consumer cooperative V. Description of the invention () Amine (1.56 g, 5 mmol, E / Z = 9/91 &gt;. The mixture was stirred at 801C for 8 hours. After the reaction was completed, water (50 ml) was added. The produced Extraction of mixture K toluene (50 ml) 2 times, M1N Wash with sodium oxide, water and saturated brine, and dry with anhydrous magnesium sulfate. Evaporate the solvent under reduced pressure to produce colorless crystals (1.53 g) (yield: 98%, E / Z = 97/3). ⑵ Toluene ( 5 ml) and titanium trioxide (25% diluted hydrochloric acid in water) (0.15 g, 0.25 mniol) was added to 2- [2- (2,5-dimethylphenoxymethyl) phenyl]- 2-methoxyiminoethylamine (1.56 g, 5ramol, E / Z = 9/91). The mixture was stirred for 8 hours. After the reaction was completed, water (50 ml) was added. The resulting mixture, M toluene (50 ml), was extracted twice, washed with a 1N sodium hydroxide aqueous solution, water and saturated brine, and dried over anhydrous magnesium sulfate. Evaporated under reduced pressure. The solvent was removed to obtain pale orange crystals (1.51 g) (yield: 97%, E / Z = 96/4). (3) Toluene (5 ml) and titanium tetrachloride (47 mg, 0.25 mmol) were added to 2- [2- &lt; 2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamidamine (1.56 g, 5 mmol, E / Z = 9/91>. The mixture was stirred at 80Ό for 24 hours. After the reaction was completed, water (50 ml) was added. The resulting mixture was extracted twice with toluene (50 ml), washed with M1N aqueous sodium hydroxide solution, water and saturated brine, and dried over anhydrous magnesium sulfate. Dry. Evaporate the solvent under reduced pressure to obtain light-colored crystals (1.56 g) (yield: 100%, E / Z = 97/3). ⑷ Toluene (5 ml), titanium tetrachloride (47 mg, 0.25 mm) and 5N hydrochlorohydrazone (0.1 ml) was added to 2- [2- (2, 5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoethyl Fluoramine (1.56 g, 5 mmol , E / Z = (please read the precautions on the back before filling in this page). Binding d This paper size applies to China National Standard (CNS) A4 specification (210x297 mm) A6 B6 Printed by the Consumer Cooperative, V. Description of the invention () 9/91). The mixture was searched at 80 ° for 2 hours. After the reaction was completed, water (50 ml) was added. The resulting mixture was extracted twice with toluene (50 ml). , M 1N aqueous sodium hydroxide solution, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain light brown crystals (1.55 g) (yield: 99%, Ε / Z = 奵 / 3 ). 17 cases of synthesis of (E) -2- (2-chloro-3-pyridyloxymethyl) -α-methoxyiminophenylacetic acid, methanol (2 ml) and 50% potassium hydroxide Aqueous solution (0.07 g, 0.66i »ido1) was added to (E) -2- (2-chloro-3-pyridyloxymethyl) -〇t-methoxyiminophenyl-acetonitrile ( 0.11 g, 0.33 minol). The mixture was stirred under reflux for 6 hours. After the reaction was completed, water <100 ml) was added, and the resulting mixture was washed with dichloromethane (50 ml). Hydrochloric acid (IN, 1 ml), the mixture was extracted twice with dichloromethane (50 ml). The dichloromethane layer was dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to give colorless crystals (E) -2 -(2-chloro-3-pyridyloxymethyl) -α-methoxyiminophenylacetic acid (0.05 g, 42.8%). 1H-NMR (CDC13) δ ppm: 4.21 (3H, s), 5.11 (2H, s), 7.11-7.52 (6H, m), 7.98-8.00 (lH, m). 1ft example synthesis of (E) -2- [2- (2-Ga-3-pyridyloxymethyl) Alkyl) phenyl] -2-methoxyimino-N-methylacetamidine 1,2-digasethane (1 ml), thionyl chloride (0.03 g, 0.28 nnnol) and dimethyl Formamidine (DMF) (0.01 ml) is added to (E) -2- (2-chloro- (please read the precautions on the back before filling in this page) -pack--cho ... Paper size applies to China National Standard (CNS) A4 specification (210X 297mm) A6 B6 V. Description of the invention () 3-pyridyloxymethyl) -α-methoxyiminophenylacetic acid (0.05g * 0.14βB01). The mixture was stirred at reflux for 1 hour. Under ice-cooling, a 40% methylamine / methanol solution (1 ml) was added to the reaction mixture. The invention was stirred for 1 hour at ου. After the reaction was completed, water (100 ml) was added, and the mixture was extracted twice with dichloromethane (50 ml). The dichloromethane layer M was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate / η-hexane) to obtain colorless crystals (E) -2- [2- (2-chloro-3-pyridyloxymethyl) benzene Group] -2-methoxyimino-N-methylacetamide (0-02 g, 42.8%). A part of it was recrystallized from ethyl acetate / n-hexane to obtain crystalline Up 128-129T). ^ -NMRfCDClj) δ ppm: 2.90 (3H, d, J = 5.5), 3.94 (3H, s), 5.10 (2H, s), 6.84 (lH, brs), 7.11-7.53 (6Η, πι), 7.95- 7.97 (lH, m) .. {Please read the notes on the back before filling out this page)-Binding. Binding line Printed by the Central Consumers Bureau of the Ministry of Economic Affairs, Consumer Cooperatives The paper is printed in accordance with China National Standard (CNS) A4 specifications ( 210X297 mm)

Claims (1)

No. 83101986 Patent reexamination application for amendments to the scope of the patent application. This revision date: January 88-a method for preparing a oxyiminoethylamine compound of the formula: A? RI where A is a Cl · 6 alkyl group , Ci_0 alkoxy, onium Ci 6 alkyl, halo, nitro or fluorenyl substituted phenyl or amidinyl; Bg_CH2〇_, -〇CH2- or _〇-; Han is ^ -6 alkyl; R1 and R2 are each independently hydrogen or (^ .6 alkyl; and the chain ~ represents any configuration of E-isomer, z-isomer, or a mixture of E- and z-isomers; the The method includes halogenating a compound of the formula (melon): OR Α. Ί Β Ν The Ministry of Economic Affairs, Central Bureau of Standards, Bureau of Work, Consumer Cooperative Cooperatives (y ^ _ III, where each symbol is as defined above to obtain a chemical formula (ιν) Compounds: -48-(Please read the notes on the back before filling out this page) The bound paper is from China's standard (CNS) Bana (210x297) No. 83101986 Patent reexamination application for amendments to the scope of the patent application. This revision date: January 88-a method for preparing a oxyiminoethylamine compound of the formula: A? RI where A is a Cl · 6 alkyl group , Ci_0 alkoxy, onium Ci 6 alkyl, halo, nitro or fluorenyl substituted phenyl or amidinyl; Bg_CH2〇_, -〇CH2- or _〇-; Han is ^ -6 alkyl; R1 and R2 are each independently hydrogen or (^ .6 alkyl; and the chain ~ represents any configuration of E-isomer, z-isomer, or a mixture of E- and z-isomers; the The method includes halogenating a compound of the formula (melon): OR Α. Ί Β Ν The Ministry of Economic Affairs, Central Bureau of Standards, Bureau of Work, Consumer Cooperative Cooperatives (y ^ _ III, where each symbol is as defined above to obtain a chemical formula (ιν) Compounds: -48-(Please read the notes on the back before filling out this page) The bound paper is from China's standard (CNS) Ba Na (210x297 public envy 397S24 A8 B8 CS D8. 'Scope of patent application cox 2. 3. where X is i and other symbols are as defined above, the compound of formula (IV) is reacted with an amine of the formula: HNRlR2 (where R1 and R2 are as defined above); where in The E-isomer content of the obtained compound is higher than the Z-isomer content. In the case of the method of applying the patent scope No. M, the method further comprises treating the obtained compound with an acid. For example, the method of claim 1 of the patent scope, wherein the compound of the chemical formula (melon) is obtained by reacting the compound of the chemical formula (Π) with a base: and (please read the precautions on the back before filling this page) OR A Printed by NBN, Shellfish Consumer Cooperative, Central Timor Bureau, Ministry of Economic Affairs Each symbol is as defined in item 1 of the scope of patent application. 4. The method of claim 3, further comprising treating the compound with an acid. This paper has been printed from CNS ～~ 297 public shame-49- Male Worker Consumer Cooperatives of Central Government Bureau of the Ministry of Economic Affairs printed 39TB24 6. Scope of patent application 5. If the scope of patent application is 帛In the method, A in hydrazone is a benzyl group which can be substituted by Ci6alkyl, kalkyl, southern Ci6, dentin, nitro, or amino. 6. The method of claim 5 in which A is an unsubstituted phenyl group. 7. The method as claimed in item 5 of the patent application, wherein A is phenyl substituted by Ci6 alkyl and / or ^^ 8. The method as claimed in item 7 of the patent application, wherein a is single or dimethyl And / or gas or fluorine substituted phenyl. 9. The method according to item 8 of the patent application, wherein a is 2,5-dimethylphenyl, 4-fluorinated phenyl, 4-chlorophenyl, 3,4-dimethylbenzyl, 2 -Methylphenyl, 2-gasified phenyl, 2-methyl-4-gasified phenyl, or 3,5-dimethylphenyl. 10. The method according to item 1 of the patent application, wherein A is a pyrimidinyl group which may be replaced by a C! -6 alkyl group, a Ct_6 alkyloxy group, a halogenated alkyl group, a halogen, a schottyl group, or a halogenated group. 11. A method as claimed in claim 10, wherein A is pyridyl substituted with halogen and / or dendritic C! -6 alkyl. 12. The method according to item 11 of the scope of patent application, wherein a is 0tb octyl substituted with gas and / or trifluoromethyl. 13. The method according to item 12 of the application, wherein a is 5-trifluoromethylpyridyl, 5-Ga-3-trifluoromethylpyridyl or 6-Ga-3_trifluorofluorenyl . 14. The method according to item 1 of the scope of patent application, where a is phenyl, 4-gas-50- This paper XJL is applicable to China National Standard (CNS) A4 specification (210X297 mm) (Please read the notes on the back first (Fill in this page again) •? Τ Rewards Α8 B8 C8 D8. 6. Application for patent scope phenyl, 4-fluorinated benzyl, 3,4-dimethylphenyl or 3,5-difluorenylphenyl 'B is; R is methyl; R1 is argon; and Na2 is fluorenyl. 15. The method according to item 1 of the scope of patent application, in which man is 2-methylbenzyl, 2-chlorobenzyl, 'gasified benzyl, 2,5_difluorenylbenzyl or 4_gas-2-_ Phenyl; B4_OCH2_; R is methyl; R1 is gas; and R2 is methyl. 16. The method according to item (1) of the scope of patent application, wherein eight is 5-trifluoromethylpyridinyl, 5-Ga-3-trifluoromethylpyridyl or 6-Ga-3_trifluoromethylpyridyl; B is -0CH2 ·; R is methyl; R1 is argon; and Han 2 is methyl. 17. The method of claim μ, wherein the compound of formula VII is its E-isomer. 18. —A method for preparing alkoxyiminoacetamido compounds of chemical formula (1): Α, '8 0R IN Printed by the Consumers' Cooperative of the Central Bureau of the Ministry of Economic Affairs, where each symbol is the i As defined in the item, the method includes combining a compound of the chemical formula 0V) with an amine of the chemical formula: HNZ (where each symbol reacts as defined in the patent application: as defined in item 1) R1 nn ^^ I Order I nnn ^ (Please first Read the notes on the reverse side and fill in this page again} k sheets of thin paper (2l0x297mm-• 51 ·, patent application scope A8 B8 C8 m cox where each symbol is as defined in item 1 of the scope of patent application; and the compound obtained by acid treatment. 19 · A compound of formula (IV): OR A B N COX IV J ^^^ 1 nil ^^^ 1! Gu nn tn K ^ i emu ^^^ 1 、 1SN (Please read the precautions on the back before filling this page) Printed by the Central naked quasi-government worker and consumer cooperative of the Ministry of Economic Affairs «. 20. where A is a benzyl or pyridyl group which can be substituted by (γδ alkyl, cw6 alkoxy, halo cU6 alkyl, sulfonium, nitro or cyano; B is -CH20-, -〇CH2 -,; R is Cu alkyl; X is halogen; and bonding ~ # Table E-isomers, Z-isomers, or mixtures of E- and Z-isomers, any configuration. A preparation chemical formula ( IV) Method of compound: OR A, BN COX IV -52- This paper U is applicable to China National Standards (CNS) A4 size (2K) X; 297 mm. Patent application scope A8 B8 C8 D8- where each symbol is as defined in item 19 of the scope of patent application, the The method includes dentifying the compound of formula (II): OR A, BN cy COOHin, wherein each symbol is as defined in item 18 of the scope of application for patent n mu ml ^^^ 1 t ^ nm m ^ a — ^ ϋ In 1'J彳 'i (Please read the precautions on the back before filling out this page) The paper size of printed bags for employees' cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 逋 Use China National Standard (CNS) A4 (210X297 mm) -53-