TW202426B - - Google Patents

Description

Such as 4 plus A6 B6 V. Description of the invention ^) The present invention is prepared by preparing E-oxime ether of the stupid glyoxylate of formula I

ch3〇-co The Ministry of Economic Affairs Central Standards Bureau employee consumer cooperative printed format in which X and Y are named 歯 素, Ci — C4 — comprehensive base, Ci — C * — alkoxy or trifluoromethyl; m is from 0 to Integer of 4; η is an integer from 0 to 3, the preparation of compound I-type oxime ethers is based on the glyoxylate esters disclosed (see, for example, European patents EP-Α 253 213 and EP-Α 254 426) 0 Monomethylhydroxylamine reaction, in which an equal amount of hydrogen chloride is formed as a by-product. However, the disadvantage of this method is that it produces a mixture of E and B isomers of oxime ethers and can only be separated industrially at a relatively high cost: moreover, isomers with better E state are usually only very low in M Quantities-The purpose of the present invention is to increase to the shortcut of compound I. We have found that this goal is achieved by the method of preparing E-oxime ethers of stupid glyoxylate I, which includes a) Convert phenol of formula I to phenate in the presence of an agent b) Mix this phenate with lactone of formula JI (please read the precautions on the back before filling in this page) 装 · 线-This paper scale is universal Chinese National Standard (CNS ) A4 specifications (210X297 mm) 10 V. Description of invention (2) A6 B6 0—c = o

III c> Remove the diluent by steaming and remove the mixture in the melt from 50 to 250¾, and d) dissolve the melt, which is still liquid, in water and acidify it. 2_phenoxymethylbenzoic acid of formula IV c = o

IV (Please read the precautions on the back before filling in this page) -Installation- -Ordered) M Conventional method and phosgene or sulfinic S [gas is converted to the corresponding formula V 2-dioxomethylbenzyl chloride { r \ y ^ cH2X ^

V c = o I Cl Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs and f) Reaction of 2-dioxymethylbenzyl chloride V with gold tester or alkaline earth metal cyanide, if required in the presence of hydrocyanic acid Next, and g) The 2-phenoxymethylbenzyl cyanide of this formula VI will be used in the paper standard of China National Standard (CTS) A 4 (210x297 g) 11 S C3 4 2 ο < 3 66 ΛΒ 5. Description of the invention (3)

It reacts with formazan in the presence of acid, h) If it is necessary to cleave the by-product of the carboxyacetyl dimethyl acetal of formula Vllb under acidic conditions (please read the precautions on the back before writing this page)

VI lb CH3O-CO and, if necessary, the α-ketocarboxamide by-product of formula Vile

Vile outfit · line · Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

Where R is hydrogen or acetyl, and then accept step (g) or i) the o-phenoxymethyl benzoate of formula Va

In Va formula, R is Wantai, and it reacts with dimethyl sulfoxide in the presence of the test, and is mixed to form 2-Via-oxymethyl I-formalic acid wax of formula Via. The paper standard is General Chinese National Standard (CNS) A 4 Specifications (210x297 mm) 12 ^ 024 £ β A 6 B6 V. Description of the invention (4)

Via and mix this mixture with methanol in the presence of an acid k) and then convert the resulting formula VI la 2-dioxomethyl glyoxylic acid methyl ester

Vila (Please read the precautions on the back before filling this page) The acetal of formula V I I b

CH30-C0 VI lb or a mixture of the compounds Vila and Vllb reacts with one of O-methylhydroxylamine or its acid addition monitor, and at the same time or later, it is treated with an acid: We have also found that this purpose can be solved by preparing Glyoxylic acid can be achieved by a one-key method, which includes the preparation of the formula v II a stupidity or printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

Vila This paper scale is in accordance with the Chinese National Standard (CNS) A4 specification (210X297 g *) V. Description of the invention (5-form Vllb glyoxylate acetal

A 6 B6

Vllb

II III IV (Please read the precautions on the back before filling in this page) Install &Order; Printed by Beigong Consumer Cooperative, Central Bureau of Standards, Ministry of Economic Affairs

This paper is used in the national standard (CNS) A 4 specifications (210x297) «:> i, 02486 A 6 B6 V. Description of the invention (6)

CH 3OH Pinner reaction-

Vila

Vllb Printed in the first step by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, the phenol of formula I is reacted with the lactone of formula I, preferably under conditions of ίίί. [Refer to, for example, Coll. Czech. 32 (1967) 3448]. Conveniently convert the resulting quinone (dioxymethyl) stearic acid IV into their gasification compounds V (compare Organikum, VEB Deutscher Verlag der Wissenschaften, 16th edition · Berl in 1986, see page 423 under M). It is converted to the corresponding benzyl cyanide VI. Finally, benzyl cyanide VI was subjected to a skin-inner ear reaction (see An ge «. Chemie 94 (1982) 1), which produced stupid glyoxylate and acetal acetal Vllb as a by-product. The latter can be converted to the compound Vila in a conventional manner by treatment with an acid such as an acid. Phenylglyoxalate VIIa and stylglyoxylic acid ST aldehyde Vllb, or a mixture of these compounds, are preferably used as starting materials for the method according to the invention. In particular, the crude product mixture of Phenyl Glyoxylate Vila and Acetyl Glyoxal Acetal Vllb can be purified without further purification. By this method, it can be converted into E-oxime ether I of phenylglyoxylate. 0-methylhydroxylamine can be used as an acid addition salt or as a free state test. It is possible to release unenzymatic compounds from the salt by adding a strong test. 0-Tongyi salts of methylhydroxylamine are especially those with monovalent to trivalent acids (please read the precautions on the back and then fill out this page)-Installation · Order-The standard of this paper is easy to use. CNS) A 4 specifications (210X297 g *) 15 A 6 B6

Jw024B6 V. Description of the invention (7) It is formed by, for example, hydrochloric acid and sulfonic acid. The reaction is generally carried out in the presence of a solvent or diluent. Suitable and preferred solvents are aromatic hydrocarbons such as stupid, toluene, and para-xylene, chloro-based hydrocarbons such as dichloromethane, yeasts such as formazan, and silver carp such as ether. A yeast is particularly preferred. The proportion of precursor suspension is not important; unless one of the sisters passes *, for example, 10 mol% is common, it is convenient to use a metered amount of the starting compound. The reaction is normally carried out from 0 to loot, preferably from 20 to 80f. A variation of this method involves the reaction of a mixture of compounds Vila and Vllb obtained from the skin-inner ear reaction (which does not have to be separated from the reaction mixture) with one of O-methylhydroxylamine or its acid addition charge. Glyoxalic acid_oxime »Usually the double bond part of M oxime is prepared by the isomer mixture of E and part of the oxime state. Once treated with K acid, the heavy sister of oxime ether will become the sister state of E. For this purpose * the crude solution can be concentrated or further diluted in advance. If necessary, it can also occur in a two-phase system composed of water / acid and an organic solvent such as dimethane. However, it is convenient to directly treat the resulting crude solution of oxime ϋ with acid without further concentration or dilution. Particularly suitable acids are AR acids, such as perchloric acid, telluric acid, phosphoric acid and hydrogen halide acids such as hydrogen hydride, aliphatic sulfonic acids such as trifluoromethanesulfonic acid • aromatic sulfonic acids such as p-methanesulfonic acid and Halogenated alkane acids such as trifluoroacetic acid. Gaseous hydrogen chloride is particularly preferred. The molar amount of acid is usually from 1 to 20 times, especially from 3 to 10 times the amount of Vila or Vila and Vllb. (Please read the precautions on the back and then fill out this page) Installed, OK-This paper is printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy. V. Description of the invention (8) A 6 B6 Isomerization is generally from -20 to 100C • Especially from 20 to 80 = 0 oxime ether • General temperature and high pressure energy, but according to the order of Danglian ore In particular, the degree of weight is about 5 times, and the eaves are carried out without the present invention. The effect takes from about 1 to 90 hours, especially 4 to 20 millimeters depending on the amount of acid. All these steps can be carried out under the atmosphere or under the bar of the system. Higher or lower pressure is also a benefit. The method can be carried out in batch-to-batch mode or even in the mine. At the time, the reactants will pass through * for example, a tubular reactor or a stirred container containing the aldehyde ester of E-oxime ether * according to the method of the present invention. The meaning of the listed compounds: halogen (please read the precautions on the back before filling this page)- . Printed by the Ministry of Central Standards Bureau employee consumer cooperative

Cl-C 4 base and ethyl ethoxy are stupidly expected to be difficult. Special Forming E can be successfully used to synthesize all stupid B as defined, especially those such as fluorine, gas alkyl such as methyl, ethyl, and isoalkoxy such as methyl, where X and Y are linked to each other and bromine; Branched or unbranched propyl and n-butyl, especially methyl-ding_ groups; Ci and trifluoroaldehyde esters are produced in high yields.

It is known that C oxy, ethoxy 1 methyl η acid »produces an oxalic ether which will decompose. E of methyl group I and the excellent method can completely synthesize different compounds. Another oxime ether is produced by the purity that occurs as before by the method according to the invention. By contrast • The same preparation method as the previous technique = 掲 示 The same difficulties will occur under acidic conditions. The preferential method is expected to be the structuring effect, because in the use of 0-methyl hydroxylamine, the amount of chlorination has been predicted. The crude product was treated with methacrylic acid, and the paper size of the oxime paper used Chinese National Standard (CNS) A 4 specifications (210x297 commonweed) 17 A 6 B6 ^ 024 ^ 6 5. Description of the invention (9) (please Read the precautions on the back first and then fill out this page) The method according to the present invention has many advantages: It can be performed in a straightforward manner under industrial regulations; '0-methylhydroxylamine can be used as an aqueous solution; stupid glyoxylate Vila can be used as a crude product from the previous stage. The dimethyl boxaldehyde that is present in its M impurities is surprisingly also converted into the desired oxime ether. The E-oxime ether I of stupid glyoxylate is described in the European case EP-A 253 213 and EP-A 254 426 as crop protection agents. Example 1 E — 2 — (dioxymethyl) phenylglyoxylic acid methyl ester 0 — methyloxime C = N ^

I

CH30-CO The Ministry of Economy Central Standards Bureau employee consumer cooperative printed 2 of 6.1 grams (22.5¾ moles)-(dioxymethyl) phenylglyoxylic acid methyl ester, and 2.1 grams (25 amil) of 0 -The mixture of methylhydroxylamine hydrochloride and 40 liters of formazan was buried for 9 hours. The solvent was then removed under reduced pressure, 100 mL of dichloromethane was added to the residue, and gaseous vaporized hydrogen was passed at 20 1C until saturated. The solution was stirred at 20 t for 12 hours and then washed with water, dried and concentrated. After grinding with cold formazan * crystallized brownish crude product. Yield: 6.3 grams. UMR (in CDCU; TMS is Ubiquitous Standard>: 7.55 ρρβ (d, 1Η), 7.40 ppm (m, 2H), 7.25 ppm (m, 3H), this paper scale uses the Chinese National Standard (CNS) A 4 specifications (210X297 g *) 18 A 6 B6 V. Description of invention (10 6.90 ppm (m, 3 Η), 4.95 ppm (s, 2H), 4.00 ppm (s, 3H), 3.85 ppm (s, 3H ) 0 Precursor 1. 1 2-(Standoxymethyl) Stochanoic Acid HC = 0

I

OH 151 grams (1.6 moles) of phenol, 106 grams of 85% heavier than potassium hydroxide aqueous solution (equivalent to 1.6 moles KOH) and 1.5 liters of dimethylbenzene were refluxed and water was continuously removed. After the water has been removed, 201 g (1.5 mol) of benphthalide and 57 liters of dimethyl methyl ether amine are added to the reaction mixture of 100 t, and the mixture is then sown at this temperature for 15 hours. After cooling to 20-25C, the product mixture was extracted twice with water 2 liters each time, and then 140 ml of 38% by weight aqueous hydrochloric acid was added. The formed crystals were separated, washed with 500 ml of water and dried. The progenitor product was purified by dissolving in 5 to 50 liters of hot propylene and re-precipitating by adding 3 liters of water. Yield: 296 g; Melting point: 125 — 1: 2 71; Printed by the employee ## cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before writing this page)

m-NMR (in CDCU; TMS is internal standard): 5.55 ppm (s · 2Η), 7.00 ppm (m, 3Η), 7.30 ppm (t, 2H) · 7.40 pp · (t, 1H), 7.65 ppm (t, 1H), 7.85 ppm (d 1 1H) & 8.20 ppm (d, 1H) 0 Precursor 1.2 2-Benzooxymethyl benzyl ether atmosphere This paper scale is easy to use China B Family Standard (CNS) A 4 specifications (210x297 g; ¢) 19 ^ 〇34S6 A 6 B6 V. Description of the invention (ll)

c = o I Cl-A mixture of 72 g (0.32 mol) 2-dioxymethyl succinic acid, 56 g (0.47 mol) sulfenic acid and 300 ml of 1,2-difluoroethane was refluxed for 3 hours . Removal of volatiles under reduced pressure produces a dark oil which slowly produces crystals. Yield: 79 grams. UMR (in CDCU; TMS is internal standard): 5.35 ppm (s, 2H) * 6.95 ppm (m · 3H) * 7.3 ppb (t, 2H), 7.5 ppm (t * 1H) * 7.7 ppb (t · 1H) > 7.85 ppm (d * 1H) »8.35 ppm (d * 1H) 0 Precursor 1. 3 2-Benzooxymethyl benzyl cyanide

Cii〇 (please read the precautions on the back before filling in this page) Pack. Order _ -Line-Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs will be 79 grams (0.32 mils) 2-benzyloxymethyl benzyl chloride, A mixture of 17 g (0.347 mol) sodium cyanide, 0.3 g (0.93 mol) tetrabutylammonium bromide, 200 liters of water and 300 ml of 1,2-difluoroethane at 20 = vigorously stirred 2 hour. Separate the phases again, and use the water phase M 100 millimetres 20 in paper size to use the Chinese National Standard (CNS) A 4 specifications (210 father 297 male dragons) A 6 B6 5. Description of the invention (12) 1 * 2 -Dichloroethane extraction. The combined organic phase M was washed three times with 100 liters each time and then dried. Removal of the solvent under reduced pressure provided 70.8 grams of brownish oil. It was triturated with methyl tertiary butyl ether / pentane (1 ·· 1) to produce a crystal. Ο UMR (in CDCU; TMS is internal standard): 8.40 ppm (d, 1H) · 8.00 ppb (d * 1H), 7.80 pp · (t, 1H), 7.60 pp · (t, 1H), 7.35 ppb (t, 2 H), 7.00 pp n (m * 3H ), 5.45 ppb (s, 2H) ° Precursor 1.4 2_ (stupyloxymethyl) stupid glyoxylate «2

C = 0 I CHjO-CO (Please read the precautions on the back before filling in this page) Binding · Ordering-Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. Gaseous hydrogen chloride is introduced into M saturated with 10 grams (42 m2) 2 -A mixture of (dioxymethyl) benzalkonium cyanide, 4.3 g (42 μm) acetic anhydride and 50 μl methyl tertiary butyl ether * while stirring at 0 to -51. After stirring at 20t for 10 hours, a solution was produced, to which 50 μl of formazan was added. The mixture was refluxed for 10 hours, and then the volatiles were removed under reduced pressure, after which the residue was dissolved in 150 ml of methyl tri-butyl ether. The organic phase M was washed twice with 100 liters of water each time, then dried and concentrated to provide 68% of the desired product and 32%. It corresponds to an oily mixture of dimethyl formaldehyde. To crack dimethyl acetaldehyde, dissolve the mixture in 50 liters of dichloromethane and stir with 10 ml of concentrated hydrochloric acid at 20 to 25 t: The paper size is controlled by China National Standard B (CNS) A4 (210x297 *) 21 A 6 B6 L024〇6 5. Description of the invention (13) (Please read the precautions on the back before filling this page) 10 hours. Separate the organic phase and wash 3 times with 50 μl each time. Intervene and concentrate. Yield: 9.7 grams (reddish oil). 'HMR (at 00 (: 1 in 13) ^ is the standard): 7.75ρρβ (τπ, 2H)., 7.60 ppb (t »1Η), 7.45 ρ ρ η (t, 1H) "» 7.3Q ppb (m, 2H), 6.95 pp · (m, 3H), 5.40 * ppm (s, 2H) and 3.80pp »(s, 3H) 〇Example 2 E — 2 — (2-methylbenzyloxymethyl) stupid B Methyl alkanoate 0 —methyl oxime 0CHj C = N ^

CH3O-CO change method 2.1. Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, 129 grams will be produced from 80% by weight 2 — (2-methylbenzyloxymethyl) phenylglyoxalate with 13% by weight 2 — (2-tolyloxymethyl) methyl glyoxylate and dimethyl acetal are mixed with .7 g (0.5 mol) of 0-methylhydroxylamine hydrochloride and 450 liters of formazan 7 hour. The mixture was cooled to 20C and 450 mL of dichloromethane was added, and 219 g (6 mol) of gaseous hydrogen trioxide was introduced. The mixture was stirred at this temperature for 15 hours * and the solvent was removed under reduced pressure. The residue is washed with cold formic acid * and then with petroleum ether and then dried. Yield: 106.8 g (colorless solid). Variation method 2.2 Will 56.8 grams of 2- (2-methylbenzylmethyl) methylbenzyl glyoxylate (90%) The paper size is common to China Sleepy Family (CNS) A4 specifications (210x297 g *) 22 Λ 6 Β6 024S6 V. Description of the invention (l4) (Please read the precautions on the back before filling in this page) Pure; 0.18 mole> 55.7 g of 0-methylhydroxylamine pain 30% strength aqueous solution (= 0.20 mole) and The mixture of 200 liters of formazan was refluxed for 7 hours. Then, at 0 to 101C • 72 grams (1.97 moles) of gaseous chloroform was added to the mixture, and 200 ml of diazomethane was added • The mixture was then stirred at 20 to 251C 3 days. The dissolved residue is removed under reduced pressure, washed with cold formaldehyde and petroleum ether, and dried again. Yield: 50.5 g. Variation method 2.3 1343 g (36.8 mol) of gaseous chloroform from -18 to- Under 810, pass 753 g (3 mol> 2 — (2-methylbenzyloxymethyl) benzyl cyanide, 3 36.6 g (3.3 mol) acetic anhydride and 2.3 liters of methyl tertiary butyl ether. In the mixture, stir the mixture at 20 to 25 1C for 36 hours and add 1.8 liters of formazan. • Bury the mixture for another 15 hours. After cooling to 20 to 25 C. • Remove the solvent under reduced pressure. • And add 1 liter of dichloromethane to the residue. The eaves phase was first washed with 80 ml of water and then added with 800 ml of splashed aqueous hydrochloric acid. • The mixture was stirred at 20 to 25 for 15 hours. After the phase separation furnace, the aqueous phase was M0. Wash with 5 liters of dichloromethane. Concentrate the combined phases. Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. Add 2 liters of yeast and 2 0.5 grams (3 moles) of Ο-methylhydroxylamine to Crude product (part 2 of the main sister (2-methylbenzyloxymethyl) methyl glyoxylate), and the mixture was circulated for 15 hours. Add 2 liters of dimethane to the reaction mixture of 20 to 25 υ Medium. Re-pass 986 grams (27 tons) of gaseous argon chloride and stir the mixture for another 48 hours. Remove the solvent under reduced pressure. The residue is washed with formic acid, water and petroleum chains and dried to produce sickle: 814 Variation method 2.4 Will 57.9 grams (0,2 moles) 2 — (2 —tolyloxymethyl) stupaldehyde acetaldehyde 23 This paper is used in the standard Β Β 戳 楳 准 (CNS.) A 4 specifications (210x297 ;) :) Λ 6 13 6 ^ 024 ^ 6 V. Description of the invention (15) (Please read the notes on the back before filling in this page) Methyl acid ester, 18.4 g · (0.2 2 0—The mixture of methylhydroxylamine acid salt and 1 3 5 ml of formazan was refluxed for 6 hours. Then 36.5 g (1.0 ′ mole) of gaseous atmosphere hydrogen was passed into the mixture at 20 1C * and the mixture was stirred at 20 1C for 24 Hours. The precipitated solids are filtered off with suction, and 100 μL of cold formazan is selected and dried. The yield is 57.2 grams. Loudness. Melting point 97-98 ”. UMR (in CDCU; TMS is internal standard): 2.22 ρρβ (3Η) • 3.8 ppm (3H) > 4.02 ppb (3H) > 4.94 ppm (2H), 6.8 ppm ( 2H) > 7.11 ppm (2H) · 7.2 ppm (1H) > 7.4 ppm (2H), 7.57 ppb (1H). The present invention also provides a method for preparing 2-oxomethyl benzoic acid of formula IV

IV c = o!

OH formula printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economy. X and Y are each halogen, Ci-c4-alkyl, Ci-c4-alkoxy or trifluoromethyl; m is an integer from 0 to 4; η It is an integer from 0 to 3. It has been revealed that 2-benzyl methyl benzoic acid is prepared by fusing phenolate with phthalide (refer to, for example, Coll. Czech. CheH. ConBun. 2 4 This paper size is commonly used in the B National Standard (CNS) A 4 specification (210x297 Public; * :) A 6 B6 Light V. Description of invention (16) (Please read the precautions on the back before filling this page) 32 (1967) 3448, J. Chen. Soc. (1964 >, 4074, German patent case DE-A 22 08 893, DE-A 24 35 613 and Meipu Patent US-A 4 282 365). In these methods • The phenol M sickle is initially converted into the corresponding phenol Η • It is then removed by steaming Solvents are embroidered as solid scorpions. However, this step can only be carried out under industrial difficulties. Because when the amount of dissolved selenium is reduced, the phenolic belly of the mixed crystal is increased. The temperature control is no longer possible because of reliable temperature. The boiling ram is extremely non-uniform c and after adding phthalide to the phenol, the solid mixture must be converted into a melt, which is costly. In addition, there are mixing problems, and it usually occurs that large phenolate melts in the stupid phthalate Harmful stirring or damage to the mixer. Another disadvantage is that the melt is treated with water in the known method. It must be cooled to room temperature. This process is very time-consuming. In addition * when using industrial rules, there must be a stirrer with a variable infeed depth so that it can be removed from the melt before cooling • or must be installed The second independent agitator is for dissolving the process. Another disadvantage of the known method is that the purity of the resulting acid should not be, but they must be purified by recrystallization of the post-mine. In addition, the output is only 60-70% The German consumer patent cooperative DE-A 2 749 957 (Example 6 > and R0 78,601) of the Central Standards Bureau of the Ministry of Economic Affairs printed German Patent Lai DE-A 2 749 957 reveals that 2-phenoxymethyl benzoic acid can be shown by combining the chain gold phenolate with stupid fc or The substituted phthalide is prepared by reaction at elevated temperature in a solvent. However, the disadvantage of this method is the long reaction time and a large amount of solvent. Furthermore, the method described in DE-A 27 49 957 in Depuerli is industrial On the contrary, the cost is high, and hydrogen is formed in the reaction due to the use of hydrogenated sodium, which means that special safety measurements are required. This paper scale uses the Chinese National Standard (CNS) A 4 specifications (210x297 male dragon) 25 A6 B6 V. Description of the invention Shortcut to compound IV. We have found that this objective can be achieved by a method of preparing 2-Benzene #ylbenzonic acid of formula IV, which includes a) converting phenol of formula I into phenolic surface in the presence of dilute_ ,

II b) Mix this phenate with lactone of formula I (please read the notes on the back before filling this page) Ι2ί ^? 〇—-c = o

III Pack · Printed by the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs C) By steaming the mixture d) While it is still special, it is usually diluted and removed from 50 to 250t. : The reaction in the melt * and the liquid will dissolve the melt in water and acidify. The sickle is suitable for the detection of metal hydroxides such as grate sodium and potassium, and the testing of yeasts such as formazan, ethylenol and formazan; hot gold is good. Note * Step ⑻ is carried out in the presence of a solvent or dilution, and the reaction is preferably carried out from 0 to loot, preferably from 20 to 80Ί0. Tongyi's solvents or diluents are aromatic hydrocarbons such as stupid, methyl stupid, postal, intermittent, and para-dimethyl stupid, enzymes such as formazan, ethyl fermentation, and isopropyl fermentation, such as tetrahydrofuran or mixtures of these solvents. A yeast and ethyl yeast are particularly good. The amount of experience is not important. Until the molar amount of the sickle is for the complete conversion of phenolic I. This paper uses the Chinese National Standard B (CNS) A 4 specifications (210X297 g *) 26 A 6 B6 V. Description of the invention (1¾ converted into corresponding It is necessary for the phenolate; it is better to use the tungsten based on the lactone II with a margin of 1 to 6 mol%. According to the present invention, the fermented compound of compound I is not separated from the formula I before mixing Ester fusion and remove the cocoon. Generally speaking, this step ⑵ is carried out from 50 to 2501, preferably from 160 to 220 1C. When the amount of solvent is reduced, the inner cooler will be converted from dissolution to liquid state. A solution of mixed phenates in lactone ϋ. Normal use of phenates and lactones at about stoichiometric ratios | but in some cases, one of the top parts may be as high as about 10% by weight. For stages ⑻ to (c >, no special pressure conditions are required, so they are conveniently carried out under atmospheric scraping force. To stop the reaction, the melt is diluted with water, advantageously while still in liquid state. The resulting solution Acidification transfer 2-Benzooxymethylbenzene from acid IV, preferably M inorganic acid such as hydrochloric acid or sulfuric acid. Success is done by conventional methods. The method according to the present invention can be carried out in batches or in continuous mines. When carried out in succession * the reactants are passed through, for example, a step reactor of a tubular reactor or a mixing vessel. The preparation method described can be Successfully used to synthesize all 2-benzyloxymethylbenzanoic acid IV as defined, especially those compounds where X and Y are each a halogen such as fluorine, gas and bromine, especially fluorine and gas;-branched or unbranched D-C4-alkyl such as methyl, ethyl, propyl and n-butyl, especially methyl and ethyl; — Ca— U — alkoxy such as methoxy, ethoxy, 1-methyl Base ethoxy and n-propoxy; (please read the precautions on the back before filling out this page) Binding · Order _ The Central Standards Bureau of the Ministry of Economic Affairs 'Consumer' Co-operative Society printed this paper. CNS) A4 specifications (210X297 g *) 27 A 6 B6 ^ 024 ^ 6 V. Description of the invention (19) One-three-methyl group. 2-Phenoxymethyl benzoic acid of formula IV can be astonishing by the present invention M The high yield and excellent purity are obtained. By contrast • The expectation from the prior art is that this method will occur as before The preparation method shown is the same difficulty. In particular, what is totally unpredictable is that after removal of the dilute cocoon from steamed noodles, Μί 銷 phenolphenol M does not precipitate into solid in the presence of 醮. Conversely, it has been expected to be difficult to stir The viscosity of the reaction mixture containing solid scorpion. Moreover, it is completely unexpected that at the highest reaction degree (about 200 C >), water can be added dropwise without melting the melt. The method according to the present invention and The previous technique has many advantages. It can be carried out in a straightforward manner. The important thing is that the intermediate _ [金 让 phenol 銸 no longer needs to be isolated as a solid • but not hissing from a solution or suspension of phenate The liquid is transformed into a melt (phenate + lactone M>). This is achieved by adding lactone U after the phenol IB has been converted to a phenate by using alkali in the presence of dilute ammonium since the diluent has subsequently been removed by distillation. Another important advantage of the method according to the invention is that it is not necessary to cool the melt • and that water is added to the liquid melt (at about 200 ° C) and cooled by reflux. During the dilution period, the reaction mixture remained easy to stir, and the temperature slowly decreased as the amount of water increased. When the addition of water is complete, the result is a clear solution of acid IV sickle salt. The acid IV precipitated by acidification is removed and washed with a little water 0.2-phenoxymethyl formic acid IV is a valuable intermediate for the synthesis of E-oxime I produced by glyoxylic acid, which is used for crop protection, Especially as a fungicide (refer to the European case of EP-Α 253 213 and EP-Α 254 426). (Please read the precautions on the back and then fill out this page) Outfit · Printed by the Beigong Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. The paper is used in the national standard (CNS) 4 specifications (210X297) * 28 o < w

66 AB 5. Description of the invention (2 ()) A particularly good way to synthesize compound I from 2-dioxymethylbenzoic acid W is stated below: C0C1 or

V-O-CH S〇C \ 2

CH

Cl

IV

C = C OH c = o j (Please read the notes on the back before filling this page)

ICHjOH / HCi -Package · Order_ Line ·

c = o CH3O-C0

Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

Vila ▽ lib This paper uses Chinese National Standard (CNS) A4 specifications (210x297 mm) 29 02 Lion Α6 Β6 V. Description of invention (21) + H2N-OCH3

C = N CH3O-CO zOCH. In this method, 2-phenoxymethylbenzoic acid is favorably converted into their gasification compounds V (refer to Organikum 'VEB Deutscher Verlag der wissenschaften, 16th edition, Berlin 1986' see (Page 423 below) • The corresponding benzyl cyanide is prepared from it: the benzal cyanide IV and the low sulfoacid are allowed to accept the inner ear reluctance (refer to angew. Chemie 94 (1982) 1) to produce stupid glyoxylate Vila and Acetal Vllb of stupid glyoxylate as a by-product. The compound Vila or Vllb or a mixture of the two and 0-methylhydroxylamine or one of its acid addition salts are reversed. The resulting mixture of E and Z isomers is treated simultaneously or steeply with M acid for subsequent Example of spring example of Z heavy sister into E isomer 3 2 — \ 2 —Medioxyloxymethyl) benzoic acid (please read the notes on the back before filling in this page) Installed--* 0- Central Bureau of Standards, Ministry of Economic Affairs Printed by Beigong Consumer Cooperative Society, c = o will be 382 grams of methanol at 30% by weight of sodium methanoate solution (this paper standard is universal Chinese National Standards (CNS) A4 specifications (210X297 g *) 30 02426 Λ 6 Β6 5 2. Description of the invention (22) Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, 2.12 mol methylphenidate) at 35K: quickly drop to 224 g (2'.08 mol) o-cresol; Rose to 501C. Stir the mixture at this temperature for 1 hour *-add another 268 grams (2 moles) of phthalide * and then remove the enzyme by steaming. Heat the resulting melt ~ 200 • Stir at this temperature for 1 hour and slowly add 1.6 liters of water. After cooling, the solution was washed twice with 0.5 μL each time and diluted with 1 μL of water. The aqueous phase was acidified to 2 with concentrated benzoic acid, after which the precipitate was removed, washed with water and dried. Yield: 89%; melting point 1541C. HMR (in CDCU; TMS is internal standard): 2.35 ρρ · (3Η), 5.55 ppm (2Η), 6.88 ρρη (2Η) · 7.15 ρρβ (2Η), 7.42 ρρ · (1Η), 7.63 ρρΒ ( 1Η) · 7.87 ρρ Brew (1Η) and 8.18 ρρ · (1Η) 0 霣 例 4 2-stupid methyl succinic acid O-CH 0 = 0 IΟΗ will be 382g in the enzyme fermentation 30% 30% The fermented sodium solution (= 2.12 moles of fermented sodium) was quickly dropped to 195.8 grams (2.08 mole) of phenol at 45t: during which the temperature rose to 521C. The mixture was stirred at 50 ° C for 1 hour, then 268 g (2 mol) of phthalocyanine was added, and then the formaldehyde was removed by distillation. The resulting melt is heated to 200C, stirred at this temperature for 1 hour, then similar

The size of this paper is based on the specifications of CNS A4 (210X297) (Please read the precautions on the back before filling out this page). Binding_ i, 024a〇Μ V. Description of invention (23 ) The method in Example 1 was gradually created. Yield: 86%; melt adhesion 132-133Ό. UMR (in the CDCU-; TMS is the internal standard): 5.55 ρρ · (2H). * 7.00 ρρ · (3H), 7.30 ppb (2H) & 7.40 pp ® (1Η), 7.65-ρρβ (1Η), 7,85 ρρ brewing (1Η) and -8.20 ρρ · (1Η). The present invention also has a "new" formula M ortho substituted benzyl cyanide < nv ^ 〇-cH2Jyi

VI (Please read the notes on the back before filling this page)

c = o I CN where X and Y are each halogen —C 4 —alkyl alkoxy or trifluoromethyl; m is the δ number from 0 to 4; η is the integer from 0 to 3. The present invention also has a method for preparing these compounds. Preparation of 2-methylpyridineiminoacetate of formula I: and its use is produced by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

C ^ H CH3O-CO .〇CH3 The present invention has a new type of lotus V. The postal position of the benzine brewing paper is replaced by the standard of the paper. The Chinese standard (CNS) A 4 specifications (210x297) "Five 、 Instructions for invention (24)

c = o I Cl A 6 B6 X and Y in the printed form of the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs are (fi element, Ci — Ca. — yaki, Ci — C4 — alkoxy or trimethyl); m is an integer from 0 to 4; η is an integer from 0 to 3. In addition to 2-benzyloxybenzylamine gas, 2- (3-n-butylphenoxymethyl) benzylamine gas 2-(3 —Third butylphenoxymethyl) benzalkonium chloride 2 — (3,4 dimethylphenoxymethyl) benzalkonium chloride, 2_ (4 — second butyl phenoxymethyl) benzalkonium chloride, And 2 — (4 monoethylphenoxymethyl) ~ 4 monomethoxybenzyl chloride. The specific meanings of the variables are as follows: .. X and Υ substituents include halogens such as fluorine, tritium, o and iodine. Preferably, it is fluorine and atmosphere; branched or unbranched D-D alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl and tertiary butyl, preferably methyl and ethyl Radicals, branched or unbranched Ci-C4-alkane radicals such as methoxy, ethoxy, n-propoxy, isopropoxy and n-butoxy, preferably methyloxy, ethoxy 1, n-propoxy and isopropoxy; trifluoromethyl · mO. 1, 2, 3 or 4 · It is 0, 1, 2, or 3, preferably (please read the precautions on the back and then fill out this page). Install &Order; The paper size is not in Chinese National Standard B (CNS) Grade 4 (210x297) *) 31 d 07 4 91 ο

66 AB V. Description of the invention (25) 0, 1 or 2; nO, 1, 2 or 3, especially 0, 1 or 2, preferably 0. In order to obtain the final product properties, the following substituted benzyl cyanide VI is preferred: 2 —dioxymethyl benzyl cyanide 2 — (2- gas phenoxymethyl) benzyl cyanide 2 — (3 — atmosphere Phenoxymethyl) benzyl cyanide 2 — (4 monochlorophenoxymethyl) benzyl sugar 2 — (2,4 diazoxyphenoxymethyl) benzyl cyanide 2 — (2-fluorophenoxymethyl) Benzyl cyanide 2 — (3-fluorophenoxymethyl) benzyl cyanide 2 — (4 monofluorophenoxymethyl) benzyl cyanide 2 — (2-methylphenoxymethyl) benzyl cyanide 2 — (3 —Methylbenzyloxymethyl) benzyl cyanide 2 — (4 monomethylbenzyloxymethyl) benzyl cyanide 2 — (2,4 dimethylphenoxymethyl) benzyl cyanide 2 — (2-methyl Benzyl 4-4-benzyloxymethyl) benzyl alcohol 2 — (2-chloro-4 4-methylbenzyloxymethyl) benzyl cyanide 2 — (2-methyl-4 fluorobenzyloxymethyl) benzyl sugar Employee consumption of the Central Standardization Bureau of the Ministry of Economic Affairs. Printed by the cooperative (please read the precautions on the back before filling in this page) 2 — (2-ethylbenzyloxymethyl) benzyl alcohol 2 — (3-ethylbenzyloxymethyl Group) benzyl cyanide 2- (4-ethyl ethyl benzoyloxymethyl) benzyl cyanide 2- (2-Ethyl-4-benzyloxymethyl) benzyl cyanide 2 — (2-Gas-4 4-ethylbenzyloxymethyl) benzyl cyanide This paper standard is universal Chinese National Standard (CNS) A4 specifications ( 210X297 Male ") 34 6 S 4 2 ο

66 AB Printed by the Beigong Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs V. Description of the invention (2 ^ 2 — (2-methyl-4 monoethylphenoxymethyl) benzyl cyanide 2 — (2-ethyl-4- Methylphenoxymethyl) benzyl cyanide 2-(2-trifluoromethylphenoxymethyl) benzyl cyanide 3-(3-trifluoromethyl phenoxymethyl) benzyl cyanide 2-(4 one three Fluoromethylbenzyloxymethyl) benzyl cyanide, the best benzylic gas V is: 2-(2-gas phenoxymethyl) benzyl alcohol atmosphere 2-(3-gas phenoxymethyl) benzyl sugar atmosphere 2-( 4 Monophenoxymethyl) benzyl chloride 2 — (2,4 dichlorobenzyloxymethyl) benzyl gas 2 2-fluorophenoxymethyl) benzylbenzene 2 — (3-fluorobenzyloxymethyl) Benzose gas 2 — (4 monofluorophenoxymethyl) benzyl sugar atmosphere 2 — (2_methylbenzyloxymethyl) benzyl gas 2 — (3 — methylbenzyloxymethyl) benzyl gas 2 — ( 4-methylphenoxymethyl) benzyl sugar gas 2 — (2,4-dimethylbenzyloxymethyl) benzyl nitrogen 2 — (2-methyl-4 monochlorophenoxymethyl) chlorobenzene I 2 — (2 — Atmosphere 4 4-methylbenzyloxymethyl) benzyl alcohol 2 — (2-methyl-4-fluorobenzyloxy Base) benzyl argon 2- (2-ethylphenoxymethyl) benzyl syrup 2-(3-ethylphenoxymethyl) benzyl alcohol 2-(4 ethyl ethyl stupid methyl) benzyl alcohol 2 — (2-Ethyl-4-phenoxymethyl) benzalkonium chloride (please read the precautions on the back before filling in this page). Packing and thread. This paper scale is easy to use China S Home Sample Standard (CNS) A 4 specifications (210X297; ")" 35 i, 〇24S6 ΑβΙ 5. Description of the invention (2 ·) 2 — (2_chloro-4 4-ethylbenzyloxymethyl) benzyl chloride 2 — (2-methyl-1 4 Monoethylphenoxymethyl) benzylamine 2 — (2-ethyl-4-methylphenoxymethyl) benzylamine 2 — (2-trifluoromethylbenzyloxymethyl ') 2 — (3-trifluoromethylbenzyloxymethyl) benzyl cyanide 2 — (4-trifluoromethylbenzyloxymethyl) benzyl cyanide is generally known for example from Angew. Che »ie 94 ( 1982) 1 (Please read the precautions on the back before filling in this page) Benzyl cyanide VI can be prepared by various methods. They normally correspond to the brewing chlorine and the generalized compound M such as gasification [Liebig's annalen 3 (1832) 249], silvering _ [Organic Synthesis Coll. Vol. 霣 (1955) 112; Angew. Cheiie 94 (1982) 1] And specifically sodium cyanide · prepared using water / organic two-phase system in the presence of a phase transfer catalyst [Tetrahedron Letters, (1974) 2275]: CN〇 装-c = o I Cl

c = o I Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

V

The VI reaction is normally carried out in an inert solvent or a mixture of soluble 0 |. In that case, it is preferable to dissolve the cyanide salt in water, and dissolve the chlorine chloride V in a solvent that is miscible or immiscible in water. The paper size is in accordance with China National Standard (CNS) Grade 4 (210x297mm) 36

^ 〇24SS Λ 6 Β6 V. Description of the invention (28) A phase transfer catalyst that reacts particularly well in a two-phase system such as quaternary ammonium or scale_ such as chloride or tetrabutylammonium bromide, methyltributyl iodide In the presence of ammonium ammonium, tetrabutyl ammonium diphoshate, trimethyl benzyl ammonium trichloride, triethyl benzyl ammonium vapor, triphenyl benzyl ammonium chloride and benzyl tributyl bromide . The preferred and preferred cyanide salt is _ metal hydride such as lithium cyanide, sodium and potassium or _ (Tujin cyanide such as magnesium cyanide, calcium or barium, especially sodium and potassium cyanide. However, it is also possible Use a mixture of these Μ and hydrocyanic acid. Examples of eaves-like cocoon dissolving or diluent for _ ^ V are aliphatic hydrocarbons such as n-pentane, n-hexane, urethane, petroleum ether, white oil and stone Oils, aromatic hydrocarbons such as stupid, methyl stupid and adjacent one, between one, or para-a stupid halogenated hydrocarbons such as two gas methane, gas imitation, tetrachloromethane, 1.2-two gas ethane, 1, 1, 2 —Trichloroethane, 1, 1, 2, 2 — Tetragas ethane, ethane and benzene, ethers such as diethyl ether, methyl tertiary butyl ether, tetrahydrofuran and dipyridane, such as ethyl acetate , Amines such as dimethylacetamide and dimethylpyridine and N-methylpyrrolidone. Normally • A mixture of cyanide salt or generalized substance in cyanic acid and the stoichiometric amount of sugar gas VM , But when the amount of cyanide salt and hydrocyanic acid is up to about 100 mol% * It is also beneficial. Please read the notes on it and then fill in this page. The amount of phase transfer catalyst printed by the Central Standards Bureau Beigong Consumer Cooperative is not important; the normal use is based on the amount of V from 0.001 to 1 mol%, and the specific catalyst is 0.01 to 5 mol96. 01 The reaction is convenient Carried out under atmospheric pressure. Higher or lower pressure is possible but generally not beneficial. The reaction is generally carried out from Ot: to the boiling point of the cocoon or its mixture, especially from 0 to 40t. Standard (CNS) A4 specifications (210X297 g; ":") 37 A 6 B6 024S6 V. Description of the invention (29) The reaction mixture box is gradually made by conventional methods. The details of the reaction must be provided. The reaction can be either batch or Continuous mining mode. When the continuous performance is carried out, the reactants are passed through the order of «such as a tube reactor or a stirring volume I * .: It is better to have a pH, examples include adding brewing chlorine ^ liquid to the stirring Cyanide salt, or a mixture of cyanide salt in hydrocyanic acid and a phase transfer catalyst. 2-Phenoxymethylbenzyl gas (V; m, η = 0) is shown in the German patent DE-A 1 279 682. In addition, the Japanese case JP-A 80/124 777 shows as 6,11 — ( Notes on the back read and then fill this page)

X and Υ in the printed form of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs are each halogen, "monoalkyl, Ci-C4-alkoxy or trifluoromethyl; m is an integer from 0 to 4; η is from 0 To the number 3 to 3; In addition to 2-phenoxymethylbenzyl cyanide, 2- (3-n-butylbenzyloxymethyl) benzyl chloride, this paper uses the Chinese National Standard (CNS) A4 specifications ( 210X297 public *) 38 Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs i.02426 A6 __B6_ V. Description of the invention (3 沴 2 — (3 —third butylphenoxymethyl) benzyl sugar gas, 2 — (3, 4 dimethylphenoxymethyl) benzyl halide, 2- (4-second butylphenoxymethyl) benzyl gas and 2- (4-ethyl ethyl oxymethyl)-4-methoxy Benzene brewing gas. They can be obtained from the conventional method box by conveniently treating carboxylic acid IV with phosgene or sulfenic acid in a hot melt or thinner (refer to Organikun * VEB Deutscher Verlag der Wissenschaften , 16th edition, Berlin 1986, see page 423 below) ° Examples of suitable solvents or dilutions are fatty smoke such as n-pentane, n-hexane, cyclohexane, petroleum ether White oil and stone oil, aromatic hydrocarbons such as stupid, toluene and o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, four gas methane, 1,2-dichloroethane, 1, 1, 2, trichloroethane, 1, 1, 2, 2-tetrachloroethane, all «ethane and triphenylene, such as ether, tetrahydrofuran and dipyridane, esters such as ethyl acetate and ketones such as acetone, Methyl ethyl formaldehyde and cyclohexyl. Humidic acid IV and gasifying agents are normally used in stoichiometric amounts, but it is preferred to use chlorinating agents up to 100 mole%. It is advantageous for catalysts such as amines Such as dimethylmethylamine, diethylmethylamine and diisobutylmethylamine; tertiary amines such as dimethylaminopyridine, diethylaminopyridine, morpholinecarboxylic acid_ and 4-N-tetrahydropyrrolyl The amount of catalytic blue which is carried out in the presence of pyridine or a phosphine oxide such as tributyl phosphine oxide can vary within wide limits. Normally use 0.01 to 50 mole% based on the amount of acid IV, especially 0.1 to 10 The catalytic rate of the ear ears (please read the precautions on the back before writing this page) Binding-Order _ This paper uses the National B Standard (CNS) A4 specifications (210X29 7 (excited) 39 A 6 B6

〇24 〔: S V. Description of the invention (31) The degree of reaction is not important, generally from 0 to loot: ## is carried out under the boiling viscosity of the solvent. Hydrogen hydride can also be conveniently prepared at atmospheric pressure. It may be at a higher or lower power level but it is generally not beneficial. The reaction mixture is gradually prepared in the conventional manner. * The reaction can be carried out in batches or in continuous mines. When consecutive performances are carried out • Pass the reactants through the steps of, for example, a tube reactor or a stirred vessel. One variation method for the preparation of benzyl cyanide VI includes the synthesis of benzyl alcohol * and it does not need to be separated from the reaction mixture or used as a crude product. deal with. Carboxylic acid IV is disclosed in the US case US-A 3 420 851, Japan case JP-A 80/124 777 and Co. 1 1. Czech Chel. Co. Organ. 32 (1967) 3 448 Prepared by the method described therein. They particularly advantageously rely on the conversion of the phenol of formula II and the internal anti-S of formula Ϊ, preferably prepared under glutinous conditions. \ ^ cn2X ^

Is0

OH IV ortho-substituted benzyl cyanide VI is the synthesis of E-oxime ether of benzaldehyde aldehyde ester I (please read the precautions on the back before filling in this page) Packed-Printed by Beigong Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs

This paper scale uses the Chinese National Standard (CNS) A 4 specifications (210X297) 40 V. Description of invention (32) Valuable middle_

C = N. CH3O-CO ^ 〇ch3 I, A6 B6 It is used for crop protection • It is preferably fungicidal (# 考 European Patent Case EP-A 253 213 and EP-A 254 426). In order to prepare the final product I, benzyl cyanide VI, or K single ion form used in their preparations, as the crude product or the K-isolated form is still soluble in the solution • Intradermal reaction with low-carbon enzymes such as formazan (Refer to Angev. Cheiie 94 (1982) 1). This produces stupal glyoxylic acid VIIa and stupid glyoxylic acid aldehyde Vllb. Subsequently, the compounds Vila and Vllb or a mixture of the two are reacted with one of O-methylhydroxylamine or one of its acid addition salts, and the resulting E / Z isomer mixture is treated simultaneously or subsequently with M acid for Yin Yi Heavy sister Z into E isomer:

CH 3OH acid (please read the precautions on the back before filling in this page) -installed-ordered_printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

VI C = 0 I CN

Vila

h2n-och: The size of this paper is generally 1 (CHS) A4 specification (210x297 mm) 41.024 ^ 5 A6 B6 V. Description of the invention (33)

CH 3 I

Example 5 2 — (2-Methylphenoxymethyl) cyanocyanine CH, C = 0 (Please read the notes on the back before filling this page) Printed Change Method A of Employees ’Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs A: First Add 890 mg (2.8 mmol) of tetra-n-butyl bromide and add 94 · 8 g (1.93 mol) of sodium cyanide dissolved in l·liter of water to 458 g (1.76 mol) 2 — (2-methylbenzyloxymethyl) benzyl »gas solution in 2 liters of toluene. The mixture was stirred at about 20X: 2 hours, and allowed to stand for 14 hours. The engraved phase is further divided, dried with sodium sulfate and concentrated under reduced pressure. The crude brown product had a purity of 91.7% (analyzed by GC) and was crystallized from 2 liters of methyl tert-butyl ether. Yield: 61%. Variation method B: 231.8 grams (0.89 mils) 2 — (2-methyl-benzyloxymethyl) This paper scale is used in China ’s standard (CNS) A 4 specifications (210x297 g *) 42 A 6 B6 o024S6 V. Description of the invention (34 solution of benzyl sugar gas in 1.55 liters of Jiaben in 1 hour, 22¾ dropwise to 48.2 g (0.98 mol) sodium cyanide, 2.5 g (7.5 gm) Ear) Vaporize a mixture of tetra-n-butylammonium and 640 liters of water. The mixture was stirred for another 14 hours, after which a phalanx was separated, washed with M 0.5 liters of water once and concentrated under reduced pressure. The product was recrystallized from 0.4 litres of hexane. Yield: 67%. Melting point 74 (yellow-brown solid). Variation method C: (reaction in the presence of hydrocyanic acid). Pack 38 grams of 19% by weight Aqueous tartaric acid (= 0.2 mol HC1) was added dropwise at 201C to a solution of 117.4 g (2.4 mol) sodium cyanide in 725 l of water. 1.4 g (4.3 mol) of tetrabutylammonium bromide and 2.4 liters of methylbenzine, and then heat the mixture to 25T: while stirring vigorously, add 521 grams (2.0 mils) of 2- (2-methylbenzyloxymethyl) benzyl chloride to 710 during the 15-minute encounter Liter toluene The solution was stirred for another 90 minutes, during which it was heated to 32t. The organic phase was separated again, washed with 200 ml of water and 200 liters of 1% by weight aqueous hydrochloric acid, and then concentrated under reduced pressure. The crude yellow product contains 93 mol% of 2- (2-methylphenoxymethyl) benzalkonium cyanide (according to HPLC). Yield: 92.5%. L-NMR (in CDC13, TMS is endogenous quasi >> : 2.3 ppb (s · 3H)! 5.4 pp (s · 2 Η): 6.7-7.0 ppm (m »2 Η); 7.1-7.3 ppm (m, 2H); 7.6 ppm (t, lH); 7.8 ppm ( t, 1H); 8.0 ppb (d, 1H); 8.3 ppm (d, 1H); IR light [cm-1]: 2220, 1665, 1600, 1573, 1496, 1242, 1131, 1060- 746, 724 ° The paper standard is used in the B a family standard (CNS) A 4 specifications (210X297 male dragon) 4 3 V. Description of the invention (35) Precursor Η 5. 1 2_ (2-methyl-benzyloxymethyl) Benzil gas

A 6 Β6

235.6 g (1.98 mol) sulfinic acid was added dropwise to 435 g (1.80 mol) at 20 to 25 t 2-(2 — methylbenzyloxymethyl> benzyl formate in 1 . 8 liters of solution in toluene. The resulting mixture was heated at 70 t: heating until gas evolution ceased (approximately 5 hours) • Zainpu. The brown oil formed (product_content 92.596) was crystallized upon cooling. Yield: 93 .596; melting point 48-511: " H-NHR (in CDC 1 3 »TMS is the internal standard): 2.3 PP (S 9 3H); 5. 3 PPM (S» 2H) 6. 7 -6 .9 PP · (m »2H) • 7.0 -7.2 PP m (m P 2H); 7.4 PPβ (t, 1Η); 7.6 PPB (t» 1H); 7.9 PPR (d, 1Η) ; 8 · 3 ppB (d P (please read the precautions on the back before filling in this page) Binding · Order _ Printed by the Ministry of Economic Affairs Bureau of Central Standards, 1H); * ·· IR Guanghua [c · -1] : 1737 · 1495, 1243, 1026, 1185, 1124 * 886 · 743, 716, 673 ° The present invention is also a novel method for preparing α-keto carboxylic acid ester of formula Vila

ch3o-co The paper size is in use .. Sleepy B family standard (CNS) A 4 specifications (210X297 mm) 44, 024 ^ 6 A 6 B6 V. Description of the invention (where X — and Y are each halogen, Ci —C * monoalkyl group, Ci—C · * —alkyloxy group or trifluoromethyl group; m is the phosphoric number from 0 to 4; η is an integer from 0 to '3. Aromatics are prepared from the corresponding benzyl cyanide Various methods of group α-keto esters are described in the literature. Angew. Chenie 68 (1956) 430 and ibid. 94 (1982Π, Org. S ynth. 2 4 (1 9 4 4) 16 M and J. D rg. C he · 29 (1964) 278 describes the method of hydrolyzing benzyl cyanide with concentrated mineral acid and converting the carboxylic acid into glyoxylic acid ester, but the formation of stearic acid ester as a by-product: γ group-^- ί = ° c = o »CN Rf〇-CO OR1 (please read the precautions on the back before filling in this page) Employee's consumer cooperation of the Central Bureau of Standards of the Ministry of Economic Affairs du printed the US patent case US-A 4 234 739, the German case DE-A 2 708 189 and Tetrah. Lett., (1980) 3539 reveal how it is possible to inhibit the formation of benzoic acid by adding halides in various types of invisible objects. It is also known to convert benzyl cyanide by the Ritter reaction. Corresponding Keto-based third-butyl S-bromoamine IX (refer to Pizhou Patent EP-A 034 240) or into N-based N—Ranyl Glycosamine X (# 考 EP-A 35 707). The two compounds can be converted to Ketone Carboxylic Acid and Ketone Ester: This paper uses Chinese Standards (CNS) A4 specifications (210x297 mm) 45, 024 A 6 B6 V. Description of the invention (37) base c = oc = o base

IX c = o base co-nh-c (ch3) CO-NH-CO-CH3 (please read the notes on the back before filling this page)

Group esterified ch3〇h group

c = o! COOH c = o I C0-0CH3 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy However, it is not possible to prepare α-ketocarboxylate VI la from benzyl cyanide VI by this method. In particular, this is shown in Angew. Che. 68, (1956) 430 and the same 94 (1982) 10 as W benzyl cyanide at room temperature, in an acid medium, in the presence of fermented intradermal reaction Produce the corresponding stupid formate and keto carboxylate. An object of the present invention is to provide a method for preparing compound Vila from benzyl cyanide VI. We found that this goal was achieved by the preparation method. It includes the new yinfangfang paper of the ketocarboxylate Vila. The paper size is used in the National B Standard (CNS) A4 specification (210x297 g *) 46, 034 ^ 6 A 6 B6 5. Description of the invention (38) a) Reaction of o-phenoxymethylbenzyl sugar of formula VI with formazan in the presence of acid,

VI

c = o I CN b) If necessary, cleave the ketocarboxylate dimethyl acetal by-product of the formula vilb under acidic conditions >

Vilb and if necessary, make the oc-carbosylamine by-product of the formula Vile and then accept step VI Ic (please read the precautions on the back before filling this page). Install * J5. Thread.

c = o I NHR-CO The printing form of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economy where R is radon or sugar base. We have also discovered the novel formula Vile's Ct-ketoacrylamide The standard of this paper is the general Chinese National Standard (CNS) A 4 specification (210x297 public address) 47 6 4 2 ❶

66 AB V. Description of Invention (39)

C = 0

I

NHR-CO where · ~ X and Y are each halogen, Ci- "monoalkyl, Cl-c4-alkoxy or tri-propyl methyl; m is an integer from 0 to 4; η is from 0 to 3 Integer and R are hydrogen or acryl and the novel formula Vila's post-dioxymethyl phenylglyoxalic acid is an intermediate (please read the precautions on the back and fill this page).

.? τ line-X 'and Y are each halogen, "-C4-alkyl: Ci-"-monoalkoxy or trifluoromethyl in the printed form of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs; m is from 0 to Integer of 4; η is an integer from 0 to 3, with the proviso that X 'is 2-chloro, 2-fluoro, 2-methyl, 4-methyl, 4-tributyl, 2- When methoxy or 2-trifluoromethyl and m is 0 or 1, or X · is 2,4-dioxan or 4-nitrogen-2, the standard paper size is used in China National Standard (CNS) A 4 Specification (210x297 g; t) 48 y. (I24v ^^ __ V. Description of the invention (4Q) When m is 2, n can be 0. N-Phenoxymethyl of formula VI used as starting material Benzyl cyanide can be prepared by, for example, the following methods: *

Cl CN (please read the precautions on the back before filling out this page). Installed: Yes _ Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs in the first stage of this method, the phenol I and phthalide I are better _Reaction under sexual conditions [see, for example, Coll. Czech. Che .. Couun. 32 »(1967) 3448]. The ortho- (phenoxymethyl) benzoic acid IV formed is conveniently converted to their chlorides V (refer to Organiku * * VEB. Deutscher Verlag der Wisspnschaften, 16th edition, Ber 1 in 1986, see page 423 M Bottom), and then prepared from a phenoxybenzyl cyanide VI. The method according to the present invention is normally carried out in emotional dissolution or dilute epilepsy. For example, in ethers such as ethyl, tetrahydrofuran and dipyridane, in chlorocarbons such as dichloromethane, trichloromethane, tetrahydromethane And dioxane • Or in aromatic hydrocarbons such as toluene, or ketone one or p-xylene. Aromatic smoke, especially toluene and two copies of paper. The BB home sample standard (CNS) A4 specification (210X297 g *) 49 A 6 B6 L02426 V. Description of the invention (4¾ Jiaben is better. The suitable acid is benzoic acid, Especially hydrochloric acid, which is preferably added to the solvent as an oxygen.

This method is particularly advantageous in the presence of water or a brewing agent of formula VI CH3-CO-L VB where L is halogen, hydroxy, methoxy or ethyl alcohol. Normally, all reactions are used at least in stoichiometric ratio * unless one of the sisters is as high as about 10 mol%. The amount of acid is preferably from 2 to 20 times of VI at most • particularly about 3 times. #When the reaction is carried out in the presence of water, the amount of water in the water is suspended from 1 to 2 times the VI. The reaction is generally at atmospheric pressure, advantageously from -80 to 80Ϊ: * particularly from -20 to 401C. The conventional method is to gradually prepare the inverted mixture. A possible by-product according to the method of the present invention is the corresponding intermediate ketocarboxylate dimethyl acetal Vllb of Vila. However, these by-products do not interfere with the subsequent synthesis of stupid glyoxylate I—oxime ether I * using ct-ketocarboxylate Vila (please read the precautions on the back before filling this page) Central Bureau of Standards, Ministry of Economic Affairs Printed by employee consumer cooperatives

I if it ’s turned to lb and then VI. Aldehydes should be condensed with methyl and diethyl esters and esterified and cleaved under the carboxyl group. The ketone strips will be sequenced under the following sequence. After the acid is waiting for the other side, it is also necessary for this paper standard to meet the national standard (CNS ) A4 specifications (210X29 · mm) 50

Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs V. Description of invention (42), for example, 掸 is introduced into chlorinated chloroform in the presence of emotional dissolution to form "-ketocarboxylic acid Vila. Moreover, in the method according to the present invention, it is possible to form the corresponding intermediate α-ketocarboxamine Vile of Vila. If you do not want the α-granyl carboxamide Vile, it is reasonable to make the crude product mixture accept this method again, if you need to repeat it several times. However, the formazan decomposition of α-ketocarboxamide Vile can also occur in separate steps, for example by treating the compound Vile with M acid, if necessary in the presence of a diluent, such as hydrocarbons such as toluene, halogenated hydrocarbons such as di Methane, trichloromethane and four gas methane, or _ such as ether, diethylgenase and dipyridine. Examples of diacids are mineral acids such as salicylic acid, sulfuric acid and phosphoric acid, carboxylic acids such as acetic acid and trigas acetic acid or sulfonic acids such as p-methanesulfonic acid. The preferred acid is bowl acid • especially concentrated aqueous solution and hydrochloric acid • it is preferably added in gaseous form. The method according to the present invention can be carried out in batches with the mine. When continuous ore is being carried out • Pass the reactants through a pipe reactor or stirring vessel. The method M according to the invention provides α-ketocarboxylate Vila in high yield and high purity. The described preparation method can be used to successfully synthesize all defined α-ketosulfonic acids, especially those compounds in which X and Υ are each selected from the group consisting of: a halogen such as fluorine, trifluoromethane, Australian public alcohol, especially fluorine and Chlorine; a branched or unbranched Ci-C alkyl group such as methyl, ethyl, n-propyl, isopropyl, isobutyl, second butyl and n-butyl; especially methyl and ethyl 9 — Branched or unbranched Dagger 1 C4-Alkyl group, such as methyl group, ethyl group, (please read the precautions on the back before filling in this page) 装-end_ 'This paper size is based on Chinese national standards ( CNS) A4 specifications (210X297 g *) 51 A 6 B6 L034 ^ 6 5. Description of the invention (43) 1 Monomethylethoxy, isopropoxy, n-butoxy, isobutoxy, and second Butoxy, n-propoxy; trifluoromethyl; m is 0, 1, 2, 3 or 4, especially 0, 1 or 2; η is 0, 1, 2 or 3, especially 0 or 1 . O-Phenoxymethyl Glyoxylic Acid of Formula Vila’_ is novel (please read the precautions on the back before filling this page)

In the printed form of the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, X 'and Y are each composed of element, Ci—C 4 —alkyl, C: — “monoalkoxy or trimethyl; m is from 0 to Integer of 4; η is the number of protons from 0 to 3. The condition is only if X 'is 2-chloro, 2-fluoro, 2-methyl, 4-methyl, 4-tert-butyl, 2-methyl When oxy or 2-trifluoromethyl and m is 0 or 1, or 5Γ is 2, 4-digas or 4-gas-2-methyl and m is 2, η can be 0. Simultaneous formula Vile The α-ketocarboxamide is novel

c = o I NHR-CO

Vile order _ line · This paper scale is used in the B national standard (CNS) A 4 specifications (210x297 mm) 52 A 6 _ B6 V. Description of the invention (44) where X and Y are each a prime, Ci-C4 An alkyl group, C! — C4 — emulsyl group or trimethyl group; m is a phosphoric number from 0 to 4; η is an integer from 0 to 3 and R is an argon or alkyl group. The specially selected α-ketocarboxylate Vila and the improved novel α-ketocarboxamide Vile can be found in Table 1. (Please read the precautions on the back before filling out this page) Packing. Order _ -Line- Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. The paper size is universal China National Standards (CNS) Grade 4 (210x297 mm) 53 534 ^ 6 A 6 B6 V. Description of invention (49 Table 1

Vila vile C = 0 j NH 2-C〇 (Please read the notes on the back before filling this page)

No.X

m Y n .001 .002 '003 .00 “.005 .006 .007 2-Γ 2- C1 3- C1 a-Cl 2々C! 2 2-CH3,“ -C1 .008 2-CH3 .009 ^ -CH3 .010 4-tert. C ^ Hg • Oil-

3-F 0 0 0 0 0 0 0 〇 0 〇 0 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs This paper scale is compliant with China National Standards (CNS) A 4 specifications (210X297 male dragon) 54 V. Invention description (

Table 1 (Continued) Number · X A 6 B6

.012 2-r- 3-F .013 2-F '3-F .0 卩 * · — F 3-F .0: 5 2-C1 2-f .016 3-C1 3-F .017 ύ- Cl 3-F 0 3 ^ -CH τ 5 ~~ .019 5-CHt 3-F .0 20-* · -CH 2 3-F 021 2-OCH3 3-r .022 2-; H2 3-F. 023 4-OCH3 3-F .024 2-CF3 3-F .025 3-CF3 3-F .026-CF 3 3-F .027 2,3-Cl2 Z 3-F .023 2f ^ -Cl2 Z 2 -F '029 2,5-C12 Z 3-F .030 2,6-C 1 2 2 3-F .031 3, "' C 1 2 2 3-F .032 3,5-Cl2 2 3-F .033 2 _CH 3, 4--C1 2 3-F .03 ^ 2-C1, 4-CH3 2 3-F .035 2-CF3, “-CH3 2 3-F .036 2-CH3, 4-CF3 2 3-F .037--3-C (Please read the precautions on the back before filling in this page) Binding · Order-Line. Printed by Beigong Consumer Cooperative, Central Bureau of Standards, Ministry of Economic Affairs: .038 2-F 1 3- CI 1.039 3-F 1 3-Cl UF 1 3-Cl; .041 2-C1 1 3-Cl 1 · 0 “2 3-Cl 1 3-Cl: .043 1 3-Cl 1.0“ 4 2-CH3 1 3-Cl:, 0 “5 3-CH3 1 3-Cl; .D46 4-CH3 3-Cl 1.047 2-OCH3 i 3-C; i .048 3-OCH3 1 3-Cl: .049 4-OCH3 1 3-C: 1.050 2-CF3 1 3-Cl 1.051 3-CF3 1 3-Cl 1.052 “-CF3 1 3-Cl 1.053 2,3-012 2 3-Cl 1.054 2 > -Cl2 2 3-Cl 1.055 2, 5-012 2 3-Cl 1 .056 2f6-Cl2 2 3-Cl The size of this paper is easy to use Chinese National Standard (CNS) A 4 specifications (210X297 g) 55 V. Description of invention () 47 Λ 6 Β6 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 1 (Grade) No. · X m Υ n .357 2 f-C 1 I-: 3-C1: 53 3,:-·: 12 2 3-Cl ▲ 059 2-C Η 2 /-* ~ C 1 2 --c 1: 60 2-C 1, -CH 2 ί 3-C1 * 061 2-cf3, ^ -ch3 2- 3-C1 062 Z-CH],-CF 3 2 3-Cl 063--3-CH3 * 06 ^ 2-F * 3-CH3 * 055 3-F: 3-CH3 1 066 uF 1 3-CH3 I 067 2-C1 1 3-CH3 063 3-C1 1 S-CH ^ 069 "-C1 1 3 -CH3 Λ 4 070 2-CH3 .1 .. 5-CH3 Λ l 071 5-CH3 1 3-CH3 1 072 ^ -CH3 j 3-CH3 Λ i 073 2-OCH3 1 3-CH3 1 07 ^ 3-OCH3 1 3-CH3 λ 075 4-OCH3 3-CH3 i. 076 2-CF3 3-CH3 * 1 077 3-CF3 1 3-CH3 i 073 4-CF3 1 3-CH3 λ 079 2,3-Cl2 2 3- CH3 1 080 2 > -Cl2 2 3-CH3 1 081 2,5-ci2 2 3-CH3 ί 082 2,6-Cl2 2 3-CH3 1 083 3, ^-Cl2 2 3-CH3 1 084 3,5- Cl2 2 3-CH3 1 L 085 2-CH3, ^ -Cl 2 3-CH3 1 086 2-Cl, / 4-CH3 2 3-CH3 1 087 2-CF3, 4-CH3 2 3-CH3 1 i 088 2 -CH3, Bu cf3 2 3-CH3 I 089--3-GCH3 I 090 2-F * 3-0CH3 I 091 2-F 1 3-0CH3 Λ 1 092 UF 1 3-0CH3 1 i. 093 2-C1 1 3-0CH3 1 094 3-C1 i 3 -0CH3 1 (Please read the precautions on the back before filling out this page) This paper is compliant with the Chinese B Family Standard (CNS) A4 specifications (210x297 gong) V. Invention description (A 6 B6 Beigong, Central Standards Bureau, Ministry of Economic Affairs Consumer Cooperative Printed Table 1 Number · (Continued) X m Y n; .09: --C1 3-OCM3 ·. 096 / — P j- | — J-0 CH 2.:. :: 97 2-C ' ri 2 * 2-OCH3 * .098 * 3-OCH 3 1; .〇〇9 2-OCH3 3-OCH3 3-0CH3 1 3-0CH3 *: ..: 0! "-och3 1 i 3-OCH3:.: 02 2-CF3-3-OCH 3 *:.: 03 3-CF3 i 3-OCH, *: .10 ^ ^ -CF 3 1 3-0CH3 1 k:.: 05 2,3-ci2 2 3-OCH3 i.;.; 06 2, “-CI2 Ί L · 3-OCH3 ▲ I. 107 2,5-C! 2 2 3-OCH3:.: 08 2,6-Cl2 ο 3-OCH3 i:.: 09 3, "-C12 2 3-OCH3 *:.: ·· 0 3,5-ci2 2 3-OCH3,» * ^. · I .. 2-CH3, «--Cl -1 3-OCH3:. :: : 2 2-C1, "-CH3 2 5-OCH3 ·:. :: 3 2-CF2," -ch3 2 3-OCH3 :: 1 ^ 2-CH3, 4-CF3 2 J-OCH3 * 1.115- -3-CF3 *:.: 16 2-F 1 3-CF3 1:,: 17 3-F 1 3-CF3 l: .113 • + -F 1 3-0 ^ 3 丄 1.119 2-C1 1 3-CF3: .1 20 3-C1 1 3-CF3 I. 121 4-C1 1 i J -CF3 i: .122 2-CH3 1 3-CF3 .1 1.123 3-CH3 1 3-CF3:.: 24 4-CH3 1 3-CF3 1 1.:25 2-OCH3 1 3-CF3 i 1. 126 3-OCH3 1 3-CF3 1: .127 4-OCH3 1 3-CF3 1 1. 123 2-CF3 3-CF3 1 1. 129 3-CF3 1 3-CF3 1.130 u-CF3 2 3-CF3 1 1.131 2 , 3-Cl2 2 3-CF3 1 1.132 2,4-Cl2 2 3-CF3 1 i (Please read the precautions on the back before filling out this page) Binding-Order _ Line ) A 4 specifications (210X297 foot) 57 A 6 B6 V. Description of the invention (49) Printed form 1 (No. X continued) by the Employees Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs m Y n:. :: 3 2, 5- Cl2 2 3-CF3:.: 3 II 2,5-Cl2 4- 2-CF3: ..: 35 3,-Cl2 2 3-CF3 '*. •• 36 5-C 1 2 2 3-CF3 «* 1 — i .. 2 2-CH3, W -'wi 2 3-CF3: 38 z -C 1, · 4-CH 3 2 3-CF3. •:. Q 2-Cr3,--CH3 3-CF, 1.;-* 0 2-CH3, 4 -CF3 2 3-CF3 ··. ·. ^ 1--1 '·. 2-F • 4-F: 1. 1 3 3-F * 4-FI 1.144 UF: 1 1.1 ^ 5 2-C1: 4-F. 1 .: "6 3-C1 * UF:« <, · 4-C1 < 4- F: :: "3 2 * CH 2 * 1. 1 2 9 3-CH3 2 **-F *:.: 50" -CH3 1 4-F 1 :: 51 2-OCH3 * 4-F 1 1 . 152 3-OCH3 I UF * 1.153 "-OCH3 1 k ~ F 1 1.; 5 ^ 2-CF3 1 1 UF 1.155 3-CF3 1 4-F 1 1.156 ^ *-CF 2 1 < 4-F 1 1.157 2,3-Cl2 2 4-FY 1.158 2.UC \ 2 2 4-F 1 1. 159 2, 5-Cl2 2 4-F 1 1. 160 2,5-Cl2 2 4-F 1 1. 161 3,4-Cl2 2 4-F 1; .152 3,5-Cl2 2 4-F i 1. 163 2-CH3, 4 -Cl 2 UF 1 I. 164 2-C1, 4- CH3 2 kF 1: .165 2-CF3, 4 -CH3 2 4—F 1;.: 66 2-CH3, 4 -cf3 2 UF 1 1.:67--uc \ 1.158 2-F 1 uc \ 1 1. 169 3-F 1 “Cl 1 1.170 4-F i 4-C1 1 (please read the precautions on the back before filling in this page). Thread-This paper scale uses the Chinese National Standard (CNS) Grade 4 (210X297mm) 58 5. Description of Invention (so) A 6 B6 Economy Number 1 printed by the Consumer Standardization Cooperative of the Central Bureau of Standards · (Continued) X mn .. 2-,: 1. ^ -Cl • 1-7 2-C1 1 〇- c 1 --C 1 -C1 1 * ^ ~ · 1 2-CH3 *-C l * ... / D 5-CH3 a-Cl I.; '6 one: Η 3 4-C 1 • 1--· .. »/ / 2-OCH3 1 ** -C 1 *:. :: 3 3-OCH3 —-C 1.179 ^ -0CH3 1-^-Cl: .130 2-CF3 1 4-C1 1: .131 3-CF3 1 iC 1 i:.: 32 U -CF2 1 4-C1 1.:33 2,3-ci2 2 "-C1:.: 34 2, -Cl2 2 4-C1 1:.: 35 2, 5-C! 2 2 U-Cl * :: Ξ6 2,6-Cl2 2 -Cl ·:; * 37 3,-C; 2 2 4-C1 1 • 1 ·-< <-] 3,5-Cl2 2 4-C1 1 1:. 139 2-CH3, Ji-Cl-Cl i:.: 90 2-C1, 4-CH3 2 4-C1 1:.; 91 2-CF3, U-CH3 2 4-C1 1: .92 2-CH3, 4-CF3 2 “-C1 1.; 93--a-Me] _ 1.19 ^ 2-F 1 4—Me i 1.195 3-F 1 4-Me i 1.196 4-F 1 4-Me 1 1.197 2-C1 1 4-He 1 1.198 3-C1 1 4-Me-I .199 4-C1 1 Me 1 I .2〇σ '-2-CH3 i * + — Me' * 1 .201 3-CH3 1 4-He 1: .202 “CH3 1 4-Me 1 1 .203 2-OCH3 1 4-—Me l 1.20“ 2-OCH3 1 4-He 1.205 4-OCH3 j ά-Μβ ί 1.206 2-CF3 1 4-Me 1 1 .207 3-CF3 1 4-Me 1.208 uq ^ 2 1 4-Ηβ 1 (please read the precautions on the back before writing this page) 210X297 Gong *) 59 Q34 ^ 〇 Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy V. Invention description (5j Form No. 1 (: Continued) • X min; .209 2,3-C 11-+ — Me»:. :: 0 1,-*-〇1 2 "-i — Mfi. •" · 2, 5-Cl2 2 4 -Me *: .212 2,5-Cl2 2 --Me 1; .213 "-C 1 2 Two-Me!: .2U 2,5-Cl2 2 — Me; .215 2-CH3, -4-C 1: 4—Me: .2: 6 2-C1, 2 4-we 1 1.217 2- CF3 / a-CH3 2 ^ -Μβ I: .213 2-CH3, 4-CF3 2 -i-Me 1: .219-hum ** — OCH ^ 1 1.220 2-F. I-OCH3; 1.221 3-F Ί 1 ^ -0CH3: 1.222 "-f 1 i * -OCH 3 ': -223 2-C1-* 4. — 〇CH 2 I: .224 3-C1" -OCH3 1: .225 -i-Cl 1 4-OCH2 · 1.226 2-CH3 "-OCH3:; .227 3-CH T 2 4-0 CH 2 1: .228 4-CH3 2 · * —OCH ^ i: .229 2-OCH3 1 4-OCH3 1 ： .230 3-OCH3 ii * -OCH 3 1 1.231 夂 -OCH3 丄 4-OCH3 1: .232 2-CF3 4-OCH3 1 1 .233 3-CF3 i U.-OCH2 1 1.234 4-CF3 1 4.-OCH3 1 1.235 2,3-Cl2 2 "-0CH3 1 1.236 2> -Cl2 2" -0CH3 1 1.23J 2,5-C] 2 2 4-OCH3 1 1.238 2,6-Cl2 2 4-OCH3 1 1 .239 3,-Cl2 2 4-OCH3 1 D0 3,5-Cl2 2 4-OCH3 1: .2k \ 2-CH3, 2 "-0CH3 1 1.242 2 -C1, "CH3 2 4-OCH3 1 1.243 2-CF3, 4-CH3 2 4-OCH3 1:, 2kU 2-CH3, 4-CF3 2 u-och3 1 1.2 ^ 5--4-CF3 1 1 .246 2-F 1 4-CF3 1 (Please read the precautions on the back before filling in this page) Binding. Order _ Thread · This paper scale uses the Chinese National Standard (CNS) A 4 specifications (210x297 public) 60 i, 〇 24S6 A 6 B6 5. Description of the invention (52)

Table 1 (continued number * X m y

JF 8 Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs ο,-2 3 .-- ί 5 6 7 8 9 ο 1 * 2 3, tt5 6 7 8 9 ο 1 2 3 4 5 * 6 7 8 9 ο 1 2 3 4 => 5 lf-5 LO 5 5 5 5 5 6 6 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 I7 7 8 S 8 8 8 2 2 2 `` · ι `` -`` * -2 <.,-.! 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 22 2 2 2 2 3-C1 Cl 2-w 3-CH2 ^ -CH * 3 2-CF3, k 2-CH3, 4 2- F 3- F 4- F 2- C1 3- C1 4- Cl 2- CH3 3- CH3 4- CH3 2- OCH3 3- OCH3 4- OCH3 2-CF3 2 2 Γ * " > ΓΟ Γ〇1 1. Η Η Η 333CC ccc FFF-I ο ο ο cc C 3 · * 2 2 2 cc CII-3, -t 5 6, ί 5 7- 《ζ 2 2 fJ3---C r 3-* ·-CF ·:-4-CF3; • --CF3. --CF3 '·-^ -CF 2 1: --CF3 II 1 4-CF3 * 1 ^ -CF3 1 ^ -CF3 I 4-CF3 i 4-CF3 i 1 4-CF3 i 4-CF3 i. 2 1 2 4-CF3 '* 1 4-CF3 1 1 2 4-CF3 1 2 4-CF3' '2 • 4 -CF3 1 -C1 2 4-CF3 1 CH3 2 > -cf3 1 -CH3 2 4-CF3 1 -cf3 2 4-CF3 1-5-F 1 1 5-F 1 1 5-F 1 1 5-F 1 1 5-F 1 1 5-F 2 1 5-F 1 1 5-F 1 1 DF 1 1 5-F 1 1 5-F 1 5-F 1 1 5-F 1 1 5-F 1 (Please read the precautions on the back before filling out this page) Pack. Line-This paper size is applicable to the national standard (CNS) A 4 specifications (210x297 mm) 61 ^ 0242; 〇A 6 B6 V. Description of invention (53) The Central Consumer ’s Bureau of the Ministry of Economic Affairs Printed by the Consumer Cooperative Society 1 Γ 纩) No. · X m Y n: .235 3-CF3 5-F \ 1.236. U-CF3 1 5-F 1; .237 2,3-ci2 2 5-F 1 1.238 2 > -Cl2 2 5-F; .239 2, 5-Π2 2 5- F i: .290 2,6-Cl2 2 5-F: 1.291 3, ^-Cl2 2 5-F 1 1 .292 3,5-Cl2 2 5-F 1 1.293 2 " CH ^, 1 2 5-F i .294 2-C1, “-CH3 2 5-F 1 1.295 2-CF3, 4-CH3 2 5-F 1 1.296 2-CH3, 4-CF3 2 5-F 1 1.297--5-C1 1 1.298 2 -F 1 5-C1 1 1.299 3-Γ 1 5-Cl i I .300 UF 1 5-C1 i 1.301 2-C1 1 5-C1 1 1.302 3-C1 1 5-C1 1 1.303 4-C1 1 5- C1 1 1.304 2-CH3 1 5-C1 -1 1.305 3-CH3 1 5-C1 1 1.306 "-CH3 1 5-C1 1 1.307 2-0CH3 1 5-C1 1 1.308 3-0CH3 1 5-C1 1 1.309 4 -OCH3 1 5-C1 1 1.310 2-CF3 1 5-Cl 1 1.311 3-CF3 1 5-C1 1 1.312 4-CF3 1 5-Cl 1 1.313 2,3-Cl2 2 5-Cl 1 1.314 i > -ci2 2 5-Cl 1 1.315 1, 5-CI2 2 5-Cl 1 1.316 2,6-C12 2 5-Cl 1 1.317 3 > -Cl2 2 5-Cl 1 1.318 3,5-Cl2 2 5-Cl 1 1.319 2 -CH3, 4-C1 2 5-Cl 1 1.320 2-C1, 4-CH3 2 5-Cl 1 1-321 2-CF3 / 4-CH3 2 5-Cl 1 1.322 2-CH3, 4-CF3 2 5- Cl -1 (Please read the precautions on the back before writing this page) Installed---Γ This paper size is used in the IIII home sample standard (CNS) A 4 specifications (210x297 g *) 62 V. Invention description (5 this

Table 1 (Grade,) Number * XA 6 B6 Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy: .223--5-Me 2-r 5-Me • 1.:-25 3-F 5-Me •:. 326 μ.-F 5-Me; 1.327 2-C1 5-Me; .323 3-C1 5-Me; 1.229 4-C1 5-Me •: .330 2-CH3 5-Me 1 1.331 3 -CH2 i 5-Me 1 1.332 Red -CH3 1 5-Me I .333 2-OCH3 1 1 5-Me 1 1.33 "3-OCH3 5-Me 1.335 4-OCH3 i 5-Me 1 1.336 2-CF3 2 5 -Me 1; .337 3-CF3 1 5-Me 1! .238 4-CF3 1 5-Me 1 1 .339 2f 3-C1 2 2 5-Me 1 I .340 2,4-Cl2 2 5-Me 1 I .341 2,5-Cl2 2 5-Me 1 1.342 2,6-Cl2 2 5-Me i 1.343 3, "-Cl2 2 5-Me 1 3,5-C12 2 5-Me 1 1.345 2 ~ CH2 , ^ &Quot; 01 2 5-Me 1 i 1.346 2-C1, 4-CH3 2 5-Me 1.347 2-CF3 / 4-CH3 2 5-Me l 1.348 2-CH3r 4-CF3 2 5-Me l 1.349- -5-OCH3 i 1.350 2-F 1 5-OCH3 I 1.35 dagger 3-F 1 5-OCH3 l 1.352 α-F / 1 5-OCH3 i 1.353 2-C1 1 5-OCH3 l 1.354 3-C1 1 5-OCH3 l 1.355 kC \ 1 5-OCH3 I 1.356 2-CH3 1 i 5-OCH3 1.357 3-CH3 i 5-OCH3 1 1.358 4-CH3 1 5-OCH3 1 1.359 2-0CH3 1 5-OCH3 1 1.360 3 -0CH3 1 5-OCH3 1 (please first Read the precautions on the back and then fill out this page) Pack. Line · The paper size is in accordance with the Chinese National Standard (CNS) A 4 specifications (210X297 mm) 63 5. Description of invention (55 A 6 B6 Employee Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs Printed Table 1 (continued) No. · X m Y n 1.261 “-OCH3 1 5-OCH3:.: 62 2-CFt i. 5-0CH3: .253 3-CF] 1 5-OCH3: 4-CF3» 1 Di-QCH3 1.255 2, 2-C 1 2 2 5-OCH3 1.266 2,-*-ci2 2 5-OCH3 1.557 2,5-Cl2 2 di-OCH2 * 1.368 2,6-Cl2 2 5-OCH3 1 .269 3, i-Cl2 2 5-OCH3 * 1.370 3,5-Cl2 2 5-OCH3 i 1.37! 2-CH3, 4-Cl 2 5-OCH3 i 1.372 2-Cl, 4-CH3 2 5-OCH3 1 1.373 2-CF3, 4-CH3 2 5-OCH3 1 1.374 2-CH3, 4-CF3 2 5-OCH3 1 1.375 *-5-CF3 i: .376 2-F i 5-CF3 1.377 3 * F 1 5-CF3 1; .378 UF 1 5-CF3 1 1.379 2-C1 1 5-CF3 * 1.330 3-C1 1 5-CF3 1 1.331 4-C1 1 5-CF3 1 i 1.382 2-CH3 1 5- CF3 1 1.383 3 * CH3 1 5-CF3 1 1.384 4-CH3 1 5-CF3 1 1 1.385 2-0CH3 1 5-CF3 1 1.386 3-OCH3 1 5-CF3 1 1.387 4-0CH3 1 5-CF3 1 1.388 2 -CF3 1 5-CF3 1 1 .3a9 3-CF3 1 5-CF3 1 1.390 KF3 1 5-CF3 1 1.391 2, 3-Clf. 2 5-CF3 1 1.392 2> -Cl2 2 5-CF3 1 1.393 2,5-Cl2 2 5-CF3 1 1.394 2,6-Cl2 2 5-CF3 1 1.395 3,4-CI2 2 5- CF3] _ 1.396 3,5-ci2 2 5-CF3 1 1.397 2-CH3, 4-C1 2 5-CF3 1.398 2-C \, 4-CH3 2 5-CF3 1 (Please read the notes on the back before filling in This page is loaded. The paper size is common in the B country sample standard (CNS) A 4 specifications (210X297 mm) 64 ^ 024δ〇 5. Description of the invention (56) A 6 Β6 Table 1 (Continued number · X · Ministry of Economic Affairs Central Printed by the Staff Consumer Cooperative of the Bureau of Standards: .599 2-CF :, 4-CH3, 5-CF ^: 1 00 --CH 2, • * -CF *; -1 i. 5-CF-.: 1] 1 --6-r… 02: -F i 5-F: +, 03 2-F 5-F: .-04-F 5-F 1. -05 2-Cl ▲ 5-F: .- 06 3- C1 * 6-F: .4〇7 "-C 1 1 6-F 1 .'08 2-CHt 1 4 6-F * 1. ^ 09 3-CH2 ▲ 6-F: .4 i 0 4-CH3 1 6-F 1 *. ** ii 2-OCH3 1 i 6-F 1 I · ， ί2 3-OCH3 1 6-F 1 1 :: 3 4-OCH3 1 6-F 1 2 -CF 2 1 6- F i: 乂 5 3-CF3 1 6-F l: .i 6 4-CF3 1 6-F 1 Λ ». 1, L. ^ I / 2, 3-C1 2 2 6-FI .-18 2, ^ -ci2 2 6-FI 1.-19 2, 5-C12 2 6-F * 1.420 2, 6-Cl2 2 6-F. ^ 21 3> -Cl2 2 6-F; .422 3,5-C12 2 6-F l .423 2-CH3, 4 -Cl 2 6-FI .424 2-C1, 4- CH3 2 6-F 1 .425 2-CF3, k -CH3 2 6-F 2. ^ 26 2-CH3, k -cf3 2 6 * F 1 .427---6-Cl 1 • “28 2 -F y 1 6-Cl 1 .429 2-F 1 6-Cl 1 .430 U.-F 1 6-Cl 1 伂 31 2-Cl 1 6-Cl 1 .432 3-C1 1 6-Cl 1. 433 4-C1 »6-Cl 1 .434 2-CH3 1 6-Cl 1 .425 3-CH3 1 6-Cl 1 .436 厶 -CH3 1 6-Cl 1 (Please read the notes on the back before filling in this Page) -Installed < Order 'line _ This paper size is easy to use Chinese a family standard (CNS) A 4 specifications (210X297 public chick) 65 A 6 B6 V. Description of invention (j Table 1 (continued) Knitted · X rn γ 2-0CH3 * 5-Cl:. ^ 23 5-0CH3 1 5-Cl: .-29 4-0CH3 1 5-CI: '4 "0 2-CF3! 5-Cl "1 3-CF3 i 6-Cl ^ -Cr3 1 5-Cl: .- ^ 3 2,2-Cl2 2 6-Cl 1. 2,4-Cl2 2 6» Cl: 1 · 2,5 -Cl2 2 6-Cl 1: · "6 2,6-Cl2 2 6-Cl 1 1 ·-· 1. ^ *** / 3,-Cl2 2 6-Cl * 1. 4 ^ 3 3,5 -Cl2 2 6-Cl 1: '"-9 9 2-CH3, 4-C1 2 6-Cl 1: .α50 2-C1, i-CH3 2 6-Cl ;-* 51 2-CF3, 4-CH3 2 6-Cl 1:, 52 2-CH3, 4-CF3 2 6-Cl 1:. "53--S-CH ^ 1 1." 5ϋ 2-F 1 6 * CH * 3 l:. "55 3-F 1 6-CH j 1:." 56 ^ -F 1 6-CH 3 1 4 D 5 7 2-C1 6-CH3 1: .453 3-C1 1 k 6-CH3; 1. ^ 59 < *-Cl 1 6-CH3 1 1. 4〇0 2-CH3 6-CH3 i- 1. "61 3-CH3 1 6-CH3 1 1." 62 4 -CH3 1 6-CH3 1 1.463 2-OCH3 1 6-CHj 1.464 3-OCH3 1 6-CH3 1.465. "-OCH3 1 6-CH3, i 1." 66 2-CFg 1 i 5-CH3 1 1. " 67 3-CF3 i 6-CH3 1 1.468 i * -CF3 l 6-CH3 1 1. "69 2,3-Cl2 2 6-CH3 1 i." 70 2 > -Cl2 2 6-CH3 1 1. ^ 71 2,5-C12 2 6--CH3 i 1.472 2,6-Cl2 2 6-CH3 1 1.473 3> -Cl2 2 6-CH3 1 1.474 3,5-Cl2 2 6-CH3 1 (please read the notes on the back first Please fill out this page again). Thread-This paper uses the Chinese B family sample (CNS) A 4 specifications (210X297 g *) 66 w〇24S6 A6 B6 V. Description of invention (5 Bow Ministry of Economics Central Standards Bureau Printed by the industrial and consumer cooperative 1-75 2-CH3, 4-c1 1. ** 76 2-C1, M.-CHrj., 4 "2-CF3, 4-CH3 i." 78 2-CH3, "CF3 1.479 -1. -1.43 2-F 1. ^ 81 3-F i. "32 4-f i.-33 2-C1 l." 34 3 -ci 1. ^ 35 4-ci 1. "86 2-CH3 1 · 437 3-CH ^ 1 ·" 38 "-CH3 1.439 2-OCH3 i. — 90 3-OCH3 1.491 4-OCH3 1.“ 92 2 -CF3 3- CF3 4- CF3 2.3- CI2 2.4- ci2 2.5- C12 2.6- CI2 3 > -Cl2 3,5-C12 2-CH3, 4-CI 2-C1, 4-CH3 2-CF3, 4-CH3 2-CH3 // 4-CF3 2- F 3- F 4- F 2- C1 3- CI “-C1 2-CH3 1.494 1.495 1.496 1.497 1.498 1. ^ 99 1.500 1.501 1.502 1.501 1.504 1.505 1.506 1.507 1.508 1.509 1.510 1.511 1.512 22222 2 6-CH3 6-CH3 6-CH 3 6-CH3 6-OCH3 6-OCH3 6-OCH3 5- OCH3 6- OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6 -OCH3 6-OCH3 6-OCH3 6-OCH ^ 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 6-OCH3 2 6-OCH3 • 6-CF3 1 6-CF3 1 6-CF 2 1 6-CF3 1 6-CF3 1 6-CF3 1 6-CF3 1 6-CF3 (please read the precautions on the back before filling in this page) Scale Xiao uses the China Sleepy Family Standard (CNS) A4 specification (210X297g *) 67

δ S 4 2 C \ I

66 AB V. Description of the invention (59) Printed form 1 (No. · X performance) of the Beigong Consumer Cooperative of the Central Standards Bureau of the Ministry of Economy m Y n 1.513 3-CH3 1 6-CF3 1: .5 U 厶 -CH 3 6 -CF3 I 1.515 2-0CH3 1 6-CF3 i 1 .516 3-OCH3 i 6-CF 2 1 k 1 _517 4-OCH3 1 6-CF3 1: .513 2-CF 3 [6-CF3 1 1.519 3- CF3 1 6-CF3 1 1.520 4-CF3 6-CF3 14 1.521 2,3-Cl2 2 6-CF 3 1 1.522 2,4-Cl2 2 6-CF3 1 1 1.523 2,5-Cl2 2 6-CF3:. 524 2,6-Cl2 2 6-CF3 1 1 1.525 3Λ-〇12 2 6-CF3 1 1.526 3,5-Cl2 2 6-CF3 1 1.527 2-CH3, 1 '-Cl 2 6-CF3 1 1.528 2- C1, -CH3 2 6-CF3 1 1.529 2-CF3,-"-CH3 2 6-CF3 1.530 2-CH3, '" -CF3 2 6-CF3 1 1.531--3,5-Cl2 1 1.532 2-F 1 3,5-Cl2 1 1.533 3-F 3,5-C12 1 1 1.534 UF 1 3,5-Cl2 1 1.535 2-C1 1 3,5-Cl2 1 1.536 3-C1 1 3,5-Cl2 1 1.537 1 3,5-Cl2 1 1.538 2-CH3 1 3,5-Cl2 1 1.539 3-CH3 1 3,5-Cl2 1 1.540 4-CH3 1 3,5-Cl2 1 1.54L 2-OCH3 1 3,5-Cl2 1 1.542 3-OCH3 1 3,5-Cl2 1 1.543 4-OCH3. 1 3,5-Cl2 1 1.544 2-CF3 1 3,5-Cl2 1 1.545 3-CF3 1 3,5-Cl2 1 1.546 4-CF3 1 3,5-Cl2 1 1.547 2,3-Cl2 2 3,5-Cl2 1 1.543 2, kC \ 2 2 3,5-Cl2 1 1.549 2,5-Cl2 2 3,5-Cl2 1 1.550 2,6-Cl2 2 3,5-Cl2 1 (please read the precautions on the back before filling in this page) 装 · 线-This paper scale is easy to use Chinese sleepy home standard (CNS) A 4 specifications (210X297 male dragon) 68 V. Description of Invention (60) A 6 B6 Printed Form 1 of the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs No. 1 (Continued) X m Y Π 1.551 3, i-Cl2 2 3,5-C1 2 1 1.552 3, 5 -Cl2 2 3,5-Cl2 1 1 .553 2-CH3, 4-C1 2 3,5-Cl2 1.554 2-C ls, “-CH] 2 3,5-C】 2: 1.555 2-CF 3, 4-CH3 2 3,5-Cl2 i 1.556 2-CH3, 4-CF3 2 3,5-Cl2 1 · l 1.557--3-C1,5-F 1 1.558 2-F 1 3-C1,5-F 1 1.559 3-F 1 3-C1,5-F 1.560 UF 1 3-C1,5-F 1 1.561 2-C1 1 3-C1,5-F 1 1.562 3-C1 1 3-C1,5-F 1 1.563 4-C1 1 3-C1,5-F 1 1.564 2-CH3 1 3-C1,5-F 1 1.565 3-CH2 1 3-C1,5-F 1 1.566 1 3-Cl, 5-F 1 1.567 2-0CH3 1 3-C1,5-F 1 i 1.568 3-0CH3 1 3-C1,5-F 1 1.569 4-OCH3 1 3-C1,5-F 1 1.570 2-CF3 1 3-C1,5- F 1 1.571 3-CF3 1 3-C1,5-F 1 1.572 4-CF3 1 3-C1,5-F 1 1.573 2,3-Cl2 2 3 -Cl, 5-F 1 1.574 2,4-Cl2 2 3-C1.5-F 1 1.575 2,5-Cl2 2 3-Cl, 5-F 1 1.576 2,6-Cl2 2 3-C1,5- F 1 1.577 3,4-Cl2 2 3-Cl, 5-F 1 1.578 3r5-Cl2 2 3-C1,5-F 1 1.579 2-CH3, 4-C1 2 3-Cl, 5-F 1 1.580 2- Cl, 4TCH3 2 3-C1,5-F 1 1.581 2-CF3, 4-CH3 2 3-C1,5-F 1 1.582 2-CH3, 4-CF3 2 3-C1,5-F 1 1.583--3 -F, 5-C1 1 1.584 2-F 1 3-F, 5-C1 1 1.585 3-F 1 3-F, 5-Cl 1 1.586 kF 1 3-F, 5-C1 1 1.587 2-C1 1 3 -F, 5-Cl 1 1.588 3-C1 1 3-F, 5-Cl 1 (please read the precautions on the back before filling in this page) Install & Order- Line. This paper standard is universal Chinese National Standard (CNS) A 4 specifications (210x297 mm) 69 ^ 024 ^ 0 V. Description of invention ("A 6 B6 Printed form 1 (Colorful) by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs No. · X m Y n 1.589 ά-ci 1 3- F, 5-C1 1 1 .590 2-CH3 1 JF, 5 * C1 «1.591 3-ch3 1 2-F, 5-C1 *: .592 4-CH3 3-F, 5-C1 I 1.593 2-OCH3 3-F, 5-C1 i 1.594 3-OCH3 ▲ 2-F, 5-C1 l 1.595 4-OCH3 1 2-Fr 5-C1 l 1.596 2-CF3 1 3-F, 5-C1 l 1.597 3-CF3 1 3-F, 5-C1 l 1.598 "CF3 i 3-F, 5-C1 I 1.599 2,3-Cl2 2 5-F, 5-C1 1 1.600 2,4-Cl2 2 2-F, 5-C1 1 1.601 2,5-Cl2 2 3-P, 5-C1 1 1 .602 2,6-Cl2 2 3-F, 5-C1 1 1.603 3,4-Cl2 2 3- F, 5-C1 1 1.604 3,5-Cl2 2 3-F, 5-C1 1 1.605 2-CH3, 4-C1 2 3-F, 5-Cl 1 1.606 2-C1, 4-CH3 2 3-F , 5-C1 i 1.607 2-CF3, 4-CH3 2 2-F, 5-Cl i 1.608 2-CH3, 4-CF3 2 3-F, 5-Cl 1 1.609--3,5,6-F3 1 1.610 2-F 1 3,5,6-F3 1 1.611 3-F 1 3,5,6-f3 1 1.612 4-F 1 3,5,6-F3 1 1.613 2-C1 1 3,5,6- F3 1 1.6H 3-C1 1 3f5,6-F3 1 1.615 ^ -Cl 1 3,5,6-F3 1 1.616 2-CH3 1 3f 5r6-F3 1 1.617 3-CH3 1 3,5,6-F3 1 1.618 4-CH3 .1 3,5,6-F3 1 1.619 2-0CH3 1 3,5,6-F3 1 1.620 3-OCH3 3,5,6-F3 1 1.621 4-OCH3 3,5,6-F3 1 1.622 2-CF3 1 3,5,6-F3 1 1.623 3-CF3 1 3,5,6-F3 1 1.624 4-CF3 1 3,5f 6-F3 1 1.625 2,3-Cl2 2 3,5, 6-F3 1 1.626 2,4-Cl2 2 3,5,6-F3 1 (Please read the precautions on the back before filling in this page) 装 · 线 & This paper size is universal Chinese National Standard (CNS) A 4 specifications (210X297mm) 70 V. Description of invention (6 is A 6 B6 M6 Consumer Printing Co., Ltd., Central Standards Bureau, Ministry of Economic Affairs, printed table number 1 (continued) • X m Y n: .627 2, 5-C1 2 2 3, 5, 6 -F3. 1.528 1, 6-C 1 2 2 3, 5,6-F3 I 1.529 3, "-Cl2 2 3,5,6-F3 1; .630 3,:-C Ί 2 2 3, 5, 6-F3 1: .531 2-CH3, 1 2 3, 5, 6-F3 1 1.632 2-C1, 4-CH 2 2 3,5,6-F3 1 1 1.633 2-CF 2, red-CH3 2 3, 5, 6-F3 1 1.634 2-CH3, 4-CF3 2 3,5,6-F3 1 1.635--3,5- (CH3) 2 1 1.636 2-F 1 3,5- (CH3) 2 1 1.637 3-F 1 3,5- (CH3) 2 1 1.538 UF 1 3,5- (CH3) 2 1 1.639 2-C1 1 3,5- (CH3) 2 1 1.640 3-C1 1 3,5- (CH3) 2 1 1 .6M 4-C1 1 3f 5- (CH3) 2 1 1.642 2 * CH3 1 3,5- (CH3) 2 1 1 .6u3 3-CH3 1 3,5- (CH3) 2 1 1.644 4-CH3 1 3,5- (CH3) 2 1 1.645 2-0CH3 1 3,5- (CH3) 2 1 1.646 3-0CH3 3,5- (CH3) 2 1 1.647 4-OCH3 1 3, 5- (CH3) 2 1 1.643 2-CF3 1 3,5- (CH3) 2 1 1.549 3-CF3 1 3,5- (CH3) 2 1 1.650 4-CF3 1 3,5- (CH3) 2 1 1.651 2,3-Cl2 2 3,5- (CH3) 2 1 1.652 lt 4-CI2 2 3f5- (CH3) 2 1 1.653 2,5-Cl2 2 3,5- (CH3) 2 1 1.654 2f 6-CI2 2 3,5- (CH3) 2 1 1.655-3,4-CI2 2 3,5- (CH3) 2 1 1.656 3,5-cy 2 3,5- (CH3) 2 1 1.657 2-CH3, '". -Cl 2 3,5- (CH3) 2 1 1.658 2-Cl, 4-CH3 2 3,5- (CH3) 2 1 1.659 2-CF3 / 4-CH3 2 3,5- (CH3) 2 1 1.660 2 -CH3, 4-CF3 2 3,5- (CH3) 2 1 1.661--5,6- (CH3) 2 1 1.662 2-F 1 5, 6- (013) 2 1 1.663 3-F 1 5,6- (CH3) 2 1 1.664 k vertical F 1 5, 6- (CH3) 2 1 (Please read the precautions on the back before filling out this page) Binding · Order * Thread · The paper size is not in accordance with China National Standards (CNS) Grade 4 (210X297mm) 71

V. Description of the invention (MA 6 B6 Printed table 1 of the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economics · (Continued) X m Y n 1.665 2-C1 5,6- (CH3) 2 1 1.566 3-C1 1 5,6 -(CH3) 2 Mo: .667 "-C1 γ 5,6- (CH3) 2 1 1 1.663 2-CH3 1 5,6- (CH3) 2 1 1.669 3-CH, 1 5,6- (CH3) 2 1.670 "-CH3 I 5,6- (CH3) 2: .671 2-OCH3 1 5,6- (CH3) 2 1.672 3-OCH3 1 5,6- (CH3) 2 1 1.673" OCH3 1 5, 6 -(CH3) 2 1 1.574 2-CF3 1 5,6- (CH3) 2 1.675 3-CF3 1 5,6- (CH3J2 l 1.676 4-CF3 1 5,6- (CH3) 2 l 1.677 2,3- Cl2 2 5,6- (CH3) 2 1 1 1.678 2, "-C] 2 2 5,6- (CH3) 2 1 1.679 2,5-Cl2 2 5,6- (CH3) 2 1 1.630 2,6 -Cl2 2 5,6- (CH3) 2 1 i 1.631 3> -Cl2 2 5,6- (CH3) 2 1 1.682 3,5-Cl2 2 5,6- (CH3) 2 1 1.633 2-CH3, 4 -Cl 2 5,6- (CH $) 2 l 1.684 2-CU "CH3 2 5,6- (CH3) 2 1 1 1.685 2-CF3, 4-CH3 2 5,6- (CH3) 2 1 1.686 2 -CH3, 4-CF3 2 5,6- (CH3) 2 1 1.687--3,4- (CH3) 2 1 1.688 2-F 1 3, "-(CH3) 2 1 1.689 3-F 1 3,4 -(CH3) 2 1 1.690 4-F 1 3,4- (CH3) 2 1 1.691 2-C1 1 3,4- (CH3) 2 1 1.692 3-C1 1 3,4- (CH3) 2 1 1.691 4 -C1 1 3,4- (CH3) 2 1 1.694 2-CH3 1. 1 3 > -(CH3) 2 1 1.695 3-CH3 1 3,4- (CH3) 2 1 1.696 4-CH3 1 3,4- (CH3) 2 1 1.697 2-OCH3 1 3,4- (CH3) 2 1 1.698 3 -OCH3 1 3,4- (CH3) 2 1 1.699 4-OCH3 1 3,4- (CH3) 2 1 1.700 2-CF3 1 3,-(CH3) 2 1 1.701 3-CF3 1 3,4- (CH3 ) 2 1 1.702 4-CF3 1 3,4- (CH3) 2 1 (Please read the precautions on the back before filling in this page) Binding · Order · Thread · This paper scale is easy to use China National Standards (CNS) A 4 Specifications (210X297 public) 72 V. Description of invention (64) A 6 B6 Table 1 No. (cont.) X m Y Π;.; 03 It 3-C 1 2 2 3,4- (CH3) 2 1;. '04 2, "-C 1 2 2 L '-(CH3) 2 1: .705 2, 2-C1 2 2 3,4- (CH3) 2 1 1.:06 2,6-C12 2 3, ( CH3) 2 1 1.707 3> -Cl2 2 3,4- (CH3) 2 1 1.708 3,5-C12 2 3,4- (CH3) 2 1 1.709 2-CH3, +-€ 1 2 3,4- (CH3) 2 1 1.710 2-C1, 4-CH3 2 2, 4- (CH3) 2 1.711 2-CF3, ^ -CH ^ 2 3,4- (CH3) 2 1 1.712 2-CH3, 4-CF3 2 3, "_ (CH3) 2 1.713--", 6- (OCH3) 2 1 1 .714 2-F 1 1 Ur 6- (OCH3) 2 i.715 3-F i ", 6- (OCH3) 2 1 1.716 kF 1 4,6- (OCH3) 2 1 1.717 2-C1 i kf 6- (OCH3) 2 1 1.718 3-C1 i kf 6- (OCH3) 2 1 1.719 4-C1 1 k, 6- (OCH3 ) 2 1 1.720 2 -CH3 1 4,6- (OCH3) 2 1 1.721 3-CH3 1 4,6- (OCH3) 2 1.722 4-CH3 1 k, 6- (OCH3) 2 i 1.723 2-0CH3 1 4,6- (OCH3 ) 2 I 1.724 3-0CH3 1 k, 6- (OCH3) 2 1 1.725 “-OCH3 1 4, 6- (0013) 2 1 1.726 2-CF3 1 4,6- (OCH3) 2 1 1.727 3-CF3 1 4,6- (OCH3) 2 1 (Please read the precautions on the back before filling out this page) Binding and ordering. -Line- Printed on paper scales of the China National Bureau of Standards, Employee and Consumer Cooperative of the Ministry of Economy CNS) A 4 specifications (210X297 mm)? 3 fj Ό A 6 B6 V. Description of the invention (65)

Table 1 Number · X (缵 m

Y η i. 728 “-CF * 3; .729 2 # 3-Ci2 1.730 2,4-Cl2: .731 2,5-Cl2: .732 2f6-Cl2: .733 3f 4-Cl2: .734 3, 5-C12, .735 2-CH3, 4-C1 ../36 2 * C1, 4-CH3 • 737 2-0 ^ 3, 4-CH3 ./38 2-CH3, 4-CF3 1 4,6- (〇CH3) 2 2 4,6- (〇CH3) 2 2 4,6- (〇CH3) 2 2 4,6- (〇CH3) 2 2 6- (OCH3) 2 2 ", 6- (OCH3) 2 2 ^, 6- (OCH3) 2 2 ", 6- (OCH3) 2 2", 6- (OCH3) 2 2 4,6- (〇CH3) 2 2 4,6- (OCH3) 2 (please first Read the precautions on the back and fill in this page) Printed by the Consumer Standardization Bureau of the Central Standards Bureau of the Ministry of Economic Affairs, the paper standard universal BS home standard (CNS) A 4 specifications (210x297) 74 ο Μ Α6 Β6 V. Description of the invention ^) ct-ketocarboxylic acid VIIa is a valuable intermediate «, especially for the · dioxomethyl benzoic acid glyoxylic acid _ 2E-after ether I · It is used for crop protection • preferably to kill Public bacteria-agents (# examination of European patent cases EP-A 253 213 and EP-A 254 426). The final product I can be relied on by adding α-alkenyl carboxylic acid Vila (when it is a crude product mixture with the dimethyl carboxylic acid ester KVIIb) to O-methyl acid or its acid "One of the reactions • The E / Z isomer mixture of the resulting oxime ethers will be treated simultaneously or post-M acid conversion. • Convert Z to the E isomer: ^ (Please read the notes on the back before filling this page ) c = o I CH 30-C0

Vila

ch2. ch3

C = N-OCH3 ο-όο Printed example 6 (according to the present invention) of the Employees ’Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 2 — (2 —methylbenzylmethyl) acetaldehyde_A_ 6.1 without diluent will be 4.1 g (40 millimoles) acetic anhydride is added to 10 g (40 * mol) 2- (2-methylbenzyloxymethyl) benzalkonium cyanide solution in 150 ml of formazan. The paper scale is not based on the Chinese standard. Bi iCNS) A 4 specifications (210X2974 *) 75 Ι Α 6 Β6 V. Description of the invention Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Then, 65 g (1.78 p.m.) of gaseous hydrogen peroxide was passed in at -5 to -10 =, and the mixture was heated to 20 C and then stirred at this pandu for about 15 hours. "Remove the ammonium trichloride formed afterwards and 100 liters of dichloromethane, and then concentrate the combined organic phase. Yield: 11.3 grams of yellow plant color solid _ analyzed by gas crocodile analysis method proved to have the following sister success:-19.3 mole 962-(2-methylbenzyloxymethyl >-benzoic acid formaldehyde (Vice-Pin product ) · -12. 9% sterol 2 — (2 — methyl stupid methyl) stupid glyoxylic acid formaldehyde (product of formula V 11 a) * —11.8 mole% 2 — (2 — methyl Dioxomethyl > phenylacetylic acid methyl dimethyl ketal K (product of formula Vllb), — 60.9 mole% 2— (2-methyl dioxomethyl) acetaldehyde acetamide (formula VI Ic Product) 6.2 Dilute cocoon (toluene) Add 30 ml of formazan and 20.4 g (0.2 p) of acetic anhydride to 50 g (0.2 mol> 2 — (2-methylphenoxymethyl) benzyl alcohol It's made in 150 liters of Jiabenzhong's earning float. Then add 22 grams (0.6 moles) of gas and argon gas at 25 to 30t: let it in, and stir the mixture for about 15 hours. Then remove the « The formed ammonium chloride and M100 liters of dicyanomethane soak, and then the combined organic phase was brewed. The niches ": 50 grams of yellow brown solid M · After analysis by gas truss method proved to have the following success: a 7.8 Moer 962 — (2-methylphenoxymethyl > Methocarbamate (the product) * a 34.1% of ears 2-(2-methylphenoxymethyl) glyoxylic acid methyl alcohol ((please read the precautions on the back before filling this page) Pack- Order *

C This paper »• Standard use of" National Standards (CNS) A 4 specifications (210X297) *) 76 A 6 B6 V. Description of invention (68) (Please read the precautions on the back before filling this page) Product > · 54.1 mol% 2- (2-methylbenzyloxymethyl) glyoxal glycosamine (product of formula Vile>. 2— (2-methylbenzyloxymethyl) benzyl K acid A -1 NMR (in CDCU; TMS is internal standard): 2.28 ρρ · (s, 3H); 3.77 ρρ · (s · 3H); 5.38 pp · (s * 2Η); 6.83 — 7.79 ρρ · ( m »8Η); 2 — (2 -methyl stupid methyl) stupaldehyde acetaldehyde amine MR MR (in CDCU; TMS is internal standard): 2.23 ρρ · (s, 3H); 5.31 ρρ · (s, 2Η); 5.81 ρρ · (br * 2Η); 6.87 — 7.99 ρρ · (m · 8Η); Example 7 (according to the invention) Conversion 2 — (2-methylbenzyloxymethyl) benzaldehyde Acetylamine is converted into 2- (2-methylbenzyloxymethyl) benzyl glyoxylate. 10 «L splashing aqueous sulfuric acid is added to 38.9% 2— (2-methylphenoxymethyl) benzyl KS {Amine and 57.6% of the ears 2- (2-methylbenzyloxygen, the Ministry of Economic Affairs, Central Bureau of Standardization, consumption cooperation Co-printed methyl) glyoxylic acid methyl alcohol (according to HPLC analysis), a solution of 39.4 g of the mixture in 200 ml of formazan. The mixture was buried for 2.5 hours and then stirred at 20-2510 for about 15 hours. HPLC analysis showed that the dissolved material now contains 81.6 mol% 2- (2-methylphenoxymethyl) -benzaldehyde glyoxylic acid methyl _ and only 1.4 mg% 2- (2-methylphenoxymethyl) benzene Acetaldehyde acetamide. After gradually preparing the mixture according to the usual usage, the crude product can be used directly to synthesize the corresponding final product of formula I. Example 8 (according to the present invention) A 4 specifications (210X297 public «) A 6 B6 V. Description of the invention (69) 2 — (2-Methylbenzylmethyl) phenylglyoxylic acid methyl dimethyl acetal cracking provides 2-(2-A Methylbenzyloxymethyl) phenylacetate methyl ester Add 100 ml of concentrated aqueous analgesic acid to 55.51 $ ear% 2-(2-methylphenoxymethyl) phenylglyoxylic acid methyl ester, 32.2 p % 2 — (2-methylphenoxymethyl) phenylethyl hexanoic acid methyl dimethyl aldehyde and 12.2 mole% 2 — (2 — methylphenoxymethyl) stearic acid methyl alcohol According to analysis by gas Bei Li precipitation method) to the solution of 130.2 g in 300 ml of a mixture of two sister atmosphere of methane. The mixture was stirred at 20-25C for 15 hours, then washed with 100 ml of water and 100 ml of concentrated aqueous sodium carbonate solution, then washed with 100 ml of water and finally dried and concentrated. Yield: 117.9 grams of yellow oil · According to analysis by gas chromatography, it contains 83.9 mol% 2- (2-methylphenoxymethyl) methyl glyoxylate and still has 12.3 mol% 2- (2-Methyl stupyloxymethyl) methyl stupate. Example 9 (Comparative prior art examples) 9.1) 2- (2-Methylbenzyloxymethyl> benzyl cyanide, MNaBr catalyzed reaction (refer to US-A Patent 4,234,739). Main reactions Formaldehyde benzoate 9.1.1 in solution: Put 20.5 g (81 millimoles> 2 — (2-methyl methoxymethyl) benzyl brewed by the Ministry of Economic Affairs Central Standards Bureau Beigong Consumer Cooperative Printed (please read the precautions on the back before filling in this page) Order-Cyanogen solution in 80 ml dichloromethane is added dropwise at 20-25C to 19.6 ml 85% by weight sulfuric acid and 1.09 g brominated The mixture. Heat the mixture to 40 t! And add 38.9 ml of formazan, and then stir the mixture at this temperature for 3 hours. The HPLC analysis of the sample indicates the quantitative formation of 2- (2-methylbenzyloxymethyl ) Stupid formic acid A_ (Do not use it as a "competitive product". This paper uses the Chinese National Standard (CNS) A 4 specifications (210x297 g *) 78 Β6 V. Invention description (? 〇) Add 100 liters of water The resulting mixture, M2 gas, was pumped twice for 50 ml * each time, and the combined organic phase was gradually made as usual. Yield: 95% competition Sex product. J 1.2 Solvent-free: add 18.9 g (78 mmol) 2- (2-methylbenzyloxymethyl) benzyl _ at about 20% to 85% of 20 ml and compare with sulfuric acid and 1. 〇g of sodium oxalate mixture. Then add 100 liters of formazan in the meantime, the whole temperature rises to 80 t and forms generalized radon. Then the mixture is stirred at 80 t: 3 hours, after cooling to about 251, Ml 00 liters of toluene is pumped._Analysis by gas phase analysis shows that this synthetic type also quantitatively forms 2- (2-methylbenzyloxymethyl) benzoic acid formaldehyde (unwanted competitive product). Melting point: 33- 37 ¾; HMR (in CDCU, TMS is the inner standard): 2.33 PP · (s, 3H); 3.87 pp · (s, 3H); 5.48 ppa (s, 2 Η); 6.83 — 8.01 pp · (m, 8 Η). 9.2) 2 — (2 -Methylphenoxymethyl) benzyl cyanide (r 丨 11 e “) reaction (Refer to EP-A 034,240 of the Pizhou Patent Case) Ministry of Economic Affairs The main reaction printed by the Central Bureau of Standards ’Staff Consumer Cooperative: the cyanide removal reaction and the alkylation of phenoxy group will save 5 grams (20 milliseconds) 2-(2-methylphenoxymethanone) 80 «L methyl tertiary The solution in ether was added to a mixture of 4.2 grams of acetic acid and 3 grams of concentrated aqueous acid at about 20 1C. The mixture was stirred for 2 hours and then 10 liters of concentrated aqueous sulfuric acid was added. The mixture was further flowed for 2 hours, and then added] _ 00 嘄 升水. Separately carved out of the face, suspicion and ba shop. Yield: 5.9 g of crude product * It has the following successes according to gas chromatography and engraving method: a 15 mol% 2- (2-methylphenoxymethyl) benzoic acid formaldehyde (no 79 (please first Read the precautions on the back and then fill out this page) This paper is compliant with the Chinese National Standard (CNS) A4 specifications (210X297; it) ^ 02428 A 6 B6 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy V. Description of invention ( 7i's competitive product), one I7 mole% 2- (2-methyl-4-a third-butyl benzoyloxymethyl, yl) methyl benzoate (unnecessary competitive product), —13 mole% N —Third butyl-2- (2-methylbenzyloxymethyl) phenylacetaldehyde acetamide, —23 mol% N di-tert-butyl-2 — (2-methyl-4 4-tert-butyl Benzene ΪΕmethyl) phenylacetaldehyde ammonium amine (unnecessary by-product). 9.3) Reaction of 2- (2'-methylbenzyloxymethyl) benzyl cyanide with sulfuric acid and acetic anhydride (refer to the Gezhou-Zhenli case EP- A 〇j5,707) The main reaction: cyanide elimination reaction and sulfonation of phenoxy group 39 grams of concentrated aqueous sulfuric acid was slowly added to 80 liters of acetic anhydride and 50 grams at 201C ( 0.199 mol) 2- (2-methylbenzyloxymethyl) mixture of benzyl cyanide. During this period, the mixture has been heated to 90 1C, cooled to 25¾, then added with 100 ml of water, and then added to a 3% aqueous solution of sodium oxide. Then remove the brown precipitate that has formed and dry it. Yield: 83.8%. 2 — (2-methyl-4-sulfophenoxymethyl) benzoic acid (unwanted product); Melting point: 242-244C. M-NMR (in d6-DMS0; TMS is the internal standard): 2.25 ppm (s, 3H); 5.50 ppd (s, 2H); 6.93-7.98 ppm (m, 7H). The present invention is also a method for preparing cx-alkenyl carboxylate of formula VI

CHtO-CO (Please read the precautions on the back before filling in this page) Binding-Order _-Line-This paper standard uses Chinese National Standard (CNS) A 4 specifications (210X297 mm) 80 δ V " 2, ο ί

66 AB V. Description of the invention (7 Including X and Y in the formula are each composed of Ciso, Ci-C * -alkyl, Ci-U-alkoxy or trifluoromethyl; m is an integer from 0 to 4; η It is an integer from 0 to 3. Various methods for preparing aromatic α-keto ft are described in the literature, but none of them has a phenoxymethyl group on the aromatic ring. So * Synth. Coiiun. 11 (1981) 943 It is shown in the GrUnard reaction to prepare phenylacetaldehyde from stupylmagnesium bromide and monoethyl diacetate (please read the precautions on the back before filling this page) 9-MgBr9 * MgBr (C〇—OC2H5) 2 (CO-OC2H5)

c = o I C jH〇5- * CO 9

c = o I Printed by C2M05-CO Employee Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs

Ange ». Chenie 68 (1956) 430 and ibid. 94 (1982) 1 ·

Org. Synth. 24 (1944) 16¾J. Org. Che .. 29 (1964) 278 Describes the method of hydrolyzing benzyl maleocyanide with M concentrated mineral acid and converting the ketocarboxylic acid into a glyoxylic acid ester * The formate is a by-product: The standard of this paper is for the use of Β Η home standard (CNS) A 4 specifications (210X297 public) 81 9 ^, 〇24 ^ β V. Description of the invention (73) [〇) ηΦ / ch 3 〇hc = o CH · Meibin Patent Case US-A 4 234 739, German B-California DE-A 2 708 189 and tetrah. Lett., (1980) 3539 shows the formation of benzoate in several situations How to be substantially suppressed by adding a halide. However, there is no way to prepare α-keto carboxylate VI because of the huge barrier to the presence of ortho-oxymethyl. The Grignard reaction therefore provides only a very low yield of ot-ketocarboxylate VI. O-Phenoxymethylbenzyl »The reaction of cyanide and formazan in the inner ear reacts with the formation of o-phenoxymethylbenzyl sugar esters». · Install h® / ch3oh

c = o I CN c = o I OCH: The thread may be derived from / 3 -ketoya * Ct-醑 based brewing, bromine by bromine in the presence of "Na" as a sickle [J. A .. Che ·. Soc. 88 (1966) 5498] or brominated with N-bromosuccinimide [Synthesis (1982) 41] and boiled with formazan in the presence of acid by Pomer (

PuBBerer) reaction prepared Βγ2 or ch3oh c = o I CM2-SCKCH3 N- bromosuccinimide HC1 c = o I Br-CH-S0-CH3 9 c = o I3O-C0 Standard (CNS) A 4 specifications (210x297 g. 4) 82 02 ^ V. Description of the invention (74) A6B6 Change method in J. Aeer. Che .. Soc., The severe conditions required for this reaction (halogenation Agent, strong acid, high temperature) and inadequate yield of keto groups • This method is also not suitable for the preparation of α-alkenyl carboxylate W. In particular, due to the huge ortho-phenoxymethyl group, a large amount of by-products can be expected * for example, the halogenation of methine groups in the aryl urethane or siloxymethyl moieties, or even the cracking of the benzyl bond. It is also known that «the conversion of benzyl cyano corresponding to the benzyl butyl butyl amine IX by the Ritter reaction (refer to Gezhou ’s case EP-A 034 240), or into the base N—emulsion X (refer to EP -A 35 707). The two compounds can be converted into amyl carboxylic acid and thionyl ester after mining:

& 〒 = 〇 CN 基基 (Please read the precautions on the back before filling out this page) 装-线 <

• -C f

IX 0 = 0

I CO-NH-C (CH3) c = o 1 CO-NHH: CM: H · Printed by Beigong Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs

r COOH-based alcohol ch3oh c = o I CO-OCHj However, ketocarboxylate VI cannot be prepared by this method 83 This paper is not used in the "« Home Sample Bi (CNS) A 4 specifications (210 X 297 g *) Μ 5. Description of the invention (75) One object of the present invention is to make compound VI more easily attainable. We have discovered this objective_The method of preparing cx-ketocarboxylate VI from Xinhao achieved * It includes: a) The formula V

Where R is L-C4-alkyl • Reaction with dimethyl sulfide in the presence of _b) Two halogenated products are added to formula Via / 3 / 3-keto sub «product

CH 2-SO-CH 3 and C) This mixture reacts with formazan in the presence of acid. We also found the novel formula VI of / 9-Ketoya »(please read the precautions on the back before filling this page) τ Printed by Beigong Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

C * 0 I CH 2-SO-CH 3 This paper uses the Chinese National Standard (CKS) Grade 4 (210X297 mm) 84

^ 〇24 & SA 6 B6 V. Description of the invention (76) where X and Y are each halogen, "-" alkyl, Ci-C4 alkoxy or trifluoromethyl; m is the number of protons from 0 to 4 ; Η is from 0 to 3 _ Ao number, and the novel formula VII 'α-keto carboxylic acid is in the middle *

(Please read the precautions on the back before filling this page) X 'and Υ in the printed form of the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs are each halogen, Ci—C * alkyl, Ct— (: 4 alkoxy or' Sanjiajia *; m is an integer from 0 to 4; η is an integer from 0 to 3 > with the proviso that only when X 'is 2-amino group 2-fluoro group, 2-methyl group, 4-methyl group , 4-tert-butyl, 2-methoxy or 2-trioxymethyl and m is 0 or 1, or X 'is 2,4-dichloro or 4-chloro-2-methyl and m When it is 2, * n may be 0. The preparation of the stupid methyl stupate of formula VI as a starting material can be achieved by, for example, reacting phenol I with phenopeptide 1 under good conditions [reference For example, Co 1 1. Czech. Che ·. Co ^ aun. 32, (1967) 3448], and H-formed to o-phenoxymethyl benzoic acid into their esters (refer to Organiku · »VEB Deutscher Verlag der Wissenschaften, 15th edition, Berlin 1977, p. 499): The BB standard (CNS) A 4 specification (210X297 mm) for this paper standard for easy use 85 -024¾¾ V. Invention description (77) A 6 B6

Printing Steps for Employees ’Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ®)-generally in the presence of sickle-soluble or dilute • for example in ethers such as tetrafuran or preferably insoluble _ in« quantity > Jiaya « In progress. Commonly suitable Λ is fermented snails such as formazan, ethyl saccharin, third butanol and third butyryl potassium, Ml alkaloid hydride such as hydrogen hydride and Mt aurantium glycosides such as amino sodium; in Formazan is conveniently used to dissolve 0! Normally o-phenoxymethyl stearic acid _VI, stoichiometric and dimethyl stoichiometric stoichiometric ratios are used, but it is also advantageous for one part of it, for example, an amount of 18 up to 10 mol%. If the reaction is carried out in solvent-free dimethyl sulfa®, the latter M will be present in large amounts. It is better to use oysters from 100 to 300 mol%. The reaction is generally carried out in the atmosphere, in which case the temperature is from 0 to 120¾, especially 50 to 701C. In step (b) • Combine / 9-Sinyl iodine VI with a chemical agent such as halogen such as 氱 or bromine. • N-halo-succinimide_imine, confirm helium or 3 · 3-dimethyl-5, 5-Dibromoethylpyrrolidine, especially bromine, N-bromosuccinimide »imine and 3,3-dimethyl-5,5-dibromoethyl bromide are mixed together, if necessary, react in the mandarin fish. The reaction is generally in eaves-based solvents or dilution_for example, smoke-like urethane or ketone (please read the precautions on the back before filling out this page) Binding-Order * Line-The National Standards (CNS) in this paper standard A4 specifications (210x297 g *) 86 A 6 B6 printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economy V. Description of invention (78) In acetone. «Examples of Yisiang are yeasts such as formazan and ethylenol and tertiary amines such as triethylamine and pyridine. Normally, / 3-Sijiya, halogenating agent and K stoichiometric ratio are used * But it is also advantageous for one of the sisters, for example, to reach a margin of 10 mol%. It is preferable to use a chemical agent from 100 to 300 mol%. This step is also conveniently carried out under atmospheric force. In this case, the temperature is from 0 to 80t: especially 20 to 65t: Finally, it will react with the / 3-faceted yal and formaldehyde in the presence of catalytic suspended mineral acid. Linyi's mineral acid is oleic acid and tellurium • especially acetic acid, which is preferably used in concentrated water solution. The amount of formazan is not important. Generally, a stoichiometric amount of hydrocarbons is used, which consists of glucan and ketone, or formazan up to about 300 mol%. If formazan is used to dissolve cocoons, it normally exists in large quantities. Apply a sloppy and powerful description of step suspicion (b). It can also be mixed and reacted with / 9-keto-sub-VI at the same time with halogenating agent, formazan and catalytic amount of acid. The reaction mixture is gradually prepared in a conventional manner. According to one variant of the method of the present invention, the method VI comprises the product VI, which is obtained from the mixture of ortho-dioxymethyldibenzoic acid V and dimethyl sulfonate without separation from the reaction mixture. • Reacts with halogenated_, and this mixture is simultaneously Or post-mine reaction with formazan in the presence of acid. The method according to the invention can be carried out in a continuous manner or in batches. In a program (please read the precautions on the back and then fill out this page) to install '-book _ This paper is based on the Chinese B Family Standard (CNS) A 4 specifications (210X297) * 〇24: .〇A 6 B6 5. In the description of the invention (79), the reactant is preferably passed through a tube-type reactor or a sump tank of a mixing vessel. According to the method of the present invention, α is provided with high yield and a very satisfactory purity.鬭 基 carboxylic acid_VI. The preparation method described can be successfully used to synthesize all of the "-Copper Carboxylic Acid VI * especially those compounds in which X and Υ each« includes: one * such as fluorine, chlorine and bromine » , Especially zhen and helium; — branched or unbranched (^ —C * -alkyl groups such as methyl, ethyl, isopropyl and n-propyl; especially methyl and ethyl; — branched or unbranched (^ — “Monoalkoxy such as methyl, ethoxy, 1-methylethoxy and n-propoxy; a trifluoromethyl; m is 0, 1, 2, 3 or 4, especially 0, 1, or 2; η is 0, 1, 2, or 3, especially 0 or 1. Some α-keto carboxylic acid esters VI have been disclosed in the European case of EP-Α 253 213.-ketone of formula VII ' Carboxylic acid »is new (please read the precautions on the back before filling in this page) Packed-Printed by Beigong Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs

In the formula, X · and γ are each rii element, Ci — c «— alkyl group, Ci ~~ c 4 — alkoxy group or trifluoromethyl group; the standard of this paper uses CN B standard (CNS) A4 specifications (210X297 Gong *) 88 A 6 B6_ V. Description of invention (b〇) m is an integer from 0 to 4; η is an integer from 0 to 3, 'The condition is only when X' is 2-chloro, 2 —Fluoro group, 2-methyl group, 4-methyl group, 4-tert-butyl group, 2-methyl gas group or 2-trimethyl gas group and m is 0 or 1 • or X ′ is 2, 4-diamine Base or 4 ~ Qi 2-A "base and m is 2." η can be 0.

Also novel is the formula VI obtained from the step (a > / 3-ketoacrylic X \ > ^ CH々 ’VI c = o

I CH 2 ~~ SO ^ CH 3 where X and Y are each composed of element, Cl — C 4, —alkyl, Cl — C 4 —alkoxy or trifluoromethyl; m is an integer from 0 to 4 ; Η is an integer from 0 to 3 * Especially suitable α-keto carboxylic acid methyl "VI" can be found in Table 1, and the preferred "one keto-iron" VI can be found in Table 2. (Please read the precautions on the back before filling out this page) Binding-Ordering-Line-Printed by the Ministry of Economic Affairs, Central Standards Bureau, Zhengong Consumer Cooperative Paper Standards General China National Standards (CNS) Grade 4 (210X297) * 89 Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs " Λ6 B6 V. Description of Invention (gi)

No.X 2.001 0 2.002 2-F 1 2.003 2-C1 1 2.004 3-C1 1 2.005 UC \ i 2.006 2, ^-Clz 2 2.007 2-CH3, "-C1 2 2.008 2-CH3 1 2.009 4-CH3 1 2.010 4-tertC4H9 1 2.on-2.012 2-F 1 2.013 3-F 1 2.014 4-F] 2.015 2-C1 2.016 3-C1 2.017 uc \ 2.018 2-CH3 2.019 3-CH3 2.020 “CH3 2.021 2 -OCH3 2.022 3-OCH3 2.023 4-G.CH3 2.024 2-CF3 0 0 0 0 0 0 0 0 0 0

VII (Please read the precautions on the back before filling in this page) Binding-Order-2.025 2.026 2.027 2.028 2.029 2.030 2.031 2.032 2.033 3-CF3 m-CF3 2f3-Cl2 2 > -Cl2 2.5- 012 2.6- Cl2 3 > -Cl2 3,5-012 2-CH3, "-C1

3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3-F 3- F 3-F 3-F 3-F 3-F 3-F 3-F 1 1 1 1 1 1 1 1 1 1 1 Thread · The size of this paper is easy to use China National Standards (CNS) A 4 specifications (210X297 mm ) 90 A 6 B 6 printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy V. Description of invention (? 2) Table 2 No. · X (performance) m Y π 2.034 2-C1, 4-CH3 2 3-F 1 2.035 2 -CF3, 4-CH3 2 3-f 1 1 2.036 2-CH3, 2 3-FX 2.037--3-C1: 2.038 2-F 1 3-C1 2.039 3-F 1 3-C1 2.040 4-F 1 3 -C1 1 2.041 2-C1 1 3-C1 1 2.042 3-C1 1 1 3-C1 i 2.043 4-C1 1 3-C1 1 2.044 2-CH3 1 3-C1 1 2.045 3-CH3 1 3-C1 1 2.046 "CH3 1 3-C1 1 2.047 2-OCH3 1 3-C1 1 2.048 3-OCH3 1 3-C1 1 2.049" OCH3 1 3-C1 1 2.050 2-CF3 1 3-C1 1 2.051 3-CF3 1 3-C1 1 2.052 u-cf3 7 3-C1 i 2.053 2,3-Cl2 2 3-C1 1 2.054 2, ^-Cl2 2 3-C1 1 2.055 2,5-Cl2 2 3-C1 1 1 2.056 2,5-Cl2 2 3-C1 I 2.057 3,4-Cl2 2 3-Cl 1 2.058 3,5-Cl2 2 3-C1 1 2.059 2-CH3, '-Cl 2 3-Cl 1 2.060 2-CU k -CH3 2 3- Cl 1 2.061 2-CF3, 4-CH3 2 3-Cl 1 2.062 2- CH3, 4-CF3 2 3-Cl 1 2.063--3-CH3 1 2.064 2-f, 1 3-CH3 1 2.065 3-F 1 3-CH3 1 2.066 4-F 1 3-CH3 i 2.067 2-C1 1 3-CH3 1 2.068 3-C1 1 3-CH3 1 2.069 4-C1 2 3-CH3 1 2.070 2-CH3 1 3-CH3 1 2.071 3-CH3 1 3-CH3 1 2.072 4-CH3 1 3-CH3 1 2.073 2-0CH3 1 3-CH3 1 (please read the precautions on the back before writing this page) Packing · This paper size is commonly used in 8 kinds of standards (CNS) A 4 specifications (210X297 public «) 91

A 6 B6 V. Description of the invention (83)

Table 2 (Continued) Number · X Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 2.074 3-OCH3 1 3-CH3 1 2.075 "-OCH3 1 3-CH3 1 2.076 Z-CF 2 1 3-CH3 1 2.077 3-CF3 1 3-CH3 1 2.078 i-CF3 1 3-CH3 1 2.079 2,3-Cl2 2 3-CH3 1 2.080 2,4-Cl2 2 3-CHj 1 2.081 2,5-Cl2 2 3-CH3 1 2.082 2, 6-Cl2 2 3-CH3 1 2.083 3,4-Cl2 2 3-CH3 1 2.084 3,5-Cl2 2 3-CH3 1 2.085 2-CH3 / 4-C1 2 3-CH3 1 2.086 2-C1, 4- CH3 2 3-CH3 1 2.087 2-CF3, 4-CH3 2 3-CH3 1 2.088 2-CH3, 4-CF3 2 3-CH3 i 2.089--3-0CH3 1 2.090 2-F 1 3-0CH3 1 2.091 3 -F 1 3-0CH3 1 2.092 4-F 1 3-0CH3 1 2.093 2-C1 1 3-0CH3 1 2.094 3-C1 1 3-0CH3 1 2.095 4-C1 1 3-0CH3 1 2.096 2-CH3 1 3- 0CH3 1 2.097 3-CH3 1 3-0CH3 1 2.098 4-CH3 1 3-0CH3 1 2.099 2-OCH3 1 3-0CH3 1 2.100 3-OCH3 1 3-0CH3 1 2.101 4-OCH3 1 3-0CH3 1 2.102 2- 0 = -3 1 3-0CH3 1 2.103 3-CF3 1 3-0CH3 1 2.104 4-CF3., 1 3-0CH3 1 2.105 2,3-C; 2 2 3-0CH3 1 2.106 2 > -Cl2 2 3- 0CH3 1 2.107 2,5-Cl2 2 3-0CH3 1 2. 10.8 2,6-Cl2 2 3-0CH3 1 2.109 3> -Cl2 2 3-0CH3 1 2.110 3,5-Cl2 2 3-0C H3 1 2.111 2-CH3, 4-C1 2 3-0CH3 1 2.112 2-C1, 4-CH3 2 3-0CH3 1 (Please read the precautions on the back before filling in this page) Binding · Binding_ Line-This paper size National Standards (CNS) Grade 4 Specification (210X297g *) 92

Ui, 024: A 6 B6 V. Description of the invention. (Printed form 2 of the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (No. · X continued) m Y π 2.113 2-CF3, i -CH3 2 3-OCH3 i 2.114 2 -CH3, 4 -cf3 2 3-OCH3 1 2.115--3-CF3 1 2.116 2-F 1 3-CF3 1 2.117 3-F 1 3-CF3 1 2.113 kF 1 3-CF3 i 2.119 2-Cl 1 3- CF 3 1 2.120 3-C1 3-CF3 2.121 "Cl i 3-CF3 1 2.122 2-ch3 l 3-CF3 1 2.123 3-CH3 1 3-CF3 1 2.124 4-CH3 1 3-CF3 1 2.125 2-0CH3 1 3-CF3 1 2.126 3-OCH3 1 3-CF3 1 2.127 "-OCH3 1 3-CF3 1 2.:28 2-CF3 1 3-CF3 * 2. 129 3-CF3 i 3-CF3 1 2.130 a-CF3 l 3-CF3] _ 2.131 2,3-Cl2 2 3-CF3 1 2.132 2Λ-〇12 2 3-CF3 1 2.133 2,5-Cl2 2 3-CF3 2.134 2,6-Cl2 2 3-CF3 1 2.135 3 > -Cl2 2 3-CF3 1 2.136 3,5-Cl2 2 3-CF3. 1 2.137 2-CH3, 4 -Cl 2 3-CF3 1 2.138 2-Cl, "CH3 2 3-CF3 1 2.139 2-CF3, k -CH3 2 3-CF3 1 2.U0 2-CH3, -CF3 2 3-CF3 1 2.U1--4-F 1 2AU2 2-F t 1 4-F 1 2.143 3-F 1 4-F 1 2.144 4-F 1 kF 1 2.145 2-Cl 1 '4-F 1 2.1 “6 3-C1 i 4-F 1 2.147 kC \ 1 4-F 1 2.148 2 -CH3 1 4-F 1 2. H9 3-CH3 1 4-F 1 2.150 4-CH3 1 4-F 1 2.151 2-0CH3 1 4-F 1 2.152 3-OCH3 1 4-F 1 2.153 4-OCH3 1 4-F 1 2.154 2-CF3 1 4-F 1 2.155 3-CF3 1 "Ink F 1 (please read the precautions on the back before filling out this page) 装 · 线 · This paper standard 8 standards for general trapping (CNS ) A 4 specifications (210X297 mm) 93 Μ V. Description of invention (85) Printed table 2 of the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy (Grade) No. · X m Y n 2.156“ -CF3 1 UF 1 2.157 2,3 -Cl2 2 kF 2.158 2 4-F 1 2.159 2,5-Cl2 2 4-F * 2.160 2,6-Cl2 2 4-F 2.151 3,4-Cl2 2 4-F 1 2.162 3,5-Cl2 2 kF 1 2.163 2-CH3, 4-C1 2 4-F 1 2. 16 夂 2-C1, "CH3 2 UF 1 2.165 2-CF3, ^ -ch3 2 4-F 1 2.166 2-CH3, a-CF " 3 2 4 —F 1 2.167--"Cl 2.168 2-F 1 4-C1 1 2.169 3-F 4-C1 1 2.170 4-F 1 1 2.171 2-C1 1 4-C1 1 2.172 3-C1 1 4-C1 1 2.173 kQ \ 1 4-C1 1 2.174 2-CH3 1 4-Cl 1 2.175 3-CH3 1 4-C1 1 2.176 4-CH3 1 4-C1 1 2.177 2-OCH3 1 4-C1 i 2.178 3-OCH3 1 4-C1 1 2.179 4-OCH3 1 kC \ '1 2.180 2-CF3 1 4-C1 1 2.181 3 -CF3 1 4-C1 1 2.182 4-CF3 1 4-C1 1 2.183 2,3-Cl2 2 4-C1 1 2.184 2> -Cl2 2 4-C1 1 2.185 2,5-Cl2 2 Bu Cl 1 2.186 2, 6-Cl2 2 4-C1 1 2.137 3 (4-Cl2, .2 4-C1 1 2.188 3,5-Cl2 2 "-C1 1 2.189 2-CH3, 4-C1 2 4-C1 1 2.190 2-Clf 4 -CH3 2 4-C1 1 2.191 2-CF3 # 4-CH3 2 4-C1 1 2.192 2-CH3, 4-CF3 2 4-C1 1 2.193--4-Me 1 2.194 2-F 1 4-—Me 1 2.195 3-F 1 4-Me 1 (Please read the precautions on the back before filling in this page) Packing. Order _ Line · This paper size is easy to use Chinese sleepy home standard (CNS) A 4 specifications (210X297 male dragon) 94 A 6 B6 Printed and printed instructions for employees ’consumer cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 66) Table 2 (continued) No. · X m Y η 2.196 UF 1 4-Me 1 2. 1 97 2-C1 1 4-Me 1 2.198 3-C1 4-Me 1 2.199 "C1 1 夂 -Me 1 2.200 2-CH3 1 4-Me 1 2.201 3-CH3 1 4-Me 1 2.202 厶 -CH3 1 4-Μβ 1 2.203 2-OCH3 1 4-He 2.204 3- OCH3 j 4—Me 1 2.205 4-OCH3 1 4-Me i 2.206 2-CF3 1 4-Me 2.207 3-CF3 1 4-Me 1 2.208 4-CF3 j 4-Me 1 2.209 2,3-C! 2 2 4-Me 2.210 2Λ-Π2 2 4-Me 1 2.211 2,5-Cl2 2 4-Me 1 1 2.212 2,6-Cl2 2 1 2.213 3Λ-〇12 2 4-He 2.214 3,5-Cl2 2 α-Μβ 2.215 2-CH3, 4-C! 2 4-Μβ 1 2.216 2-C1, “-CH3 2 4—Μβ 1 2.217 2-CF3, 4-CH3 2 4-Μβ 2,218 2-CH3, 4-CF3 2 4-Me 1 2.219-— 4-OCH3 1 2.220 2-F 1 4-OCH3 1 2.221 3-F 1 '· OCH3 1 2.222 kF 1 4-OCH3 1 2.223 2-C1 1 4-OCH3 1 2.224 3-C1 1 4-OCH3 1 2.225 4-C1 1 4-OCH3 ▲ 2.226 2-CH3 / 1 4-OCH3 2.227 3 -CH3 1 4-OCH3 1 2.228 4-CH3 1 4-OCH3 1 2.229 2-OCH3 1 4-OCH3 1 2.230 3-OCH3 1 4-OCH3 1 2.231 4-OCH3 1 4-OCH3 1 2.232 2-CF3 1 4- OCH3 1 2.233 3-CF3 1 4-OCH3 1 2.234 4-CF3 1 4-OCH3 1 (please read the precautions on the back before filling in this page). Thread-This paper size is used in China National Standard (CNS) A 4 Specifications (210X297 Gongchi) 95 A 6 B6 V. Description of the invention (8) Printed form 2 (cont.) No. * X m Y n 2.235 2,3-C 12 2 "- OCH3 1 2.236 2, i-Cl2 2 "-OCH3 1 2.237 2,5-C12 2 4-OCH3 1 2.238 2,6-C 12 2 4-OCH3 1 2.239 3,"-Cl2 2 4-OCH3 1. 2.240 3 , 5-C 12 2 4-OCH3 2.241 2-CH3, i * -ci 2 4-OCH3 1 2.242 2-C1, if-CH3 2 4-OCH3 i 2.243 2-CF3, 4-CH3 2 4-OCH3 1 l.2ku 2-CH3 , 4-CF3 2 4-OCH2 1 2.245--4-CF3 1 2.246 2-F 1 U-CF2 1 2.247 3-F 1 4-CF3 1 2_2 “3 4-F 1 4-CF3 1 2.249 2-C1 1 4-CF3 1 2.250 3-C1 1 4-CF3 1 2.251 "Cl 1 4-CF3 1 2.252 2-CH3 1 4-CF3 1 2.253 3-CH3 1 4-CF3 1 2.254" -CH3 1 4-CF3 1 2.255 2 -OCH3 1 4-CF3 1 2.256 3-0CH3 1 4-CF3 1 2.257 "-OCH3 1 4-CF3 1 2.258 2-CF3 1 4-CF3 1 2.259 3-CF3 1 4-CF3 1 2.260 U-CF2 1 4- CF3 1 2.261 2, 3-ci2 2 4-CF3 1 2.262 2, "-Cl2 2 4-CF3 1 2.263 2,5-Cl2 2 4-CF3 1 2.264 2,6-Cl2 2 4-CF3 1 2.265 3,4 -Cl2 s 2 4-CF3 1 2.266 3,5-Cl2 2 4-CF3 1 2.267 2-CH3, 4-C1 2 4-CF3 1 2.268 2-C1, ^ -CH3 2 4-CF3 1 2.269 2-CF3, 4-CH3 2 4-CF3 1 2.270 2-CH3, 4-CF3 2 4-CF3 1 2.271 2.272 2-F 1 5-F 5-F 1 1 2.273 3-F 1 5-F 1 2.27k 4-F 1 5-F 1 (Please read the precautions on the back before filling in this page) This paper size is easy to use China National Standards (CNS) A 4 specifications (210X297 mm) 96 A 6 B6 Member of the Central Standards Bureau of the Ministry of Economic Affairs Printed by industrial and consumer cooperatives · _ i / Γ ^ 〇: 4.- V. Description of the invention (88) Table 2 (continued)

No. X m Υ η 2.275 2-C1 1 5-F l 2.276 3-C1 1 5-F 1 2.277 "C1 1 5-F 2.278 2-ΟΗβ 1 5-F 1 2.279 3-CH3 1 5-F 1 2.230 i-CH3 5-F 2.231 2-OCH3 1 5-F 2.282 3-OCH3 1 5-F 1 1 2.283 "OCH3 1 5-F 1 i 2.284 2-CF3 1 5-FI 2.235 3-CF3 5-F 1 2.236 4-CF3 1 5-F 1 2.287 2,3-Cl2 2 5-F 1 2.238 2,4-Cl2 2 5-F 1 2.289 2,5-Cl2 2 5-F 1 2.290 2,6-Cl2 2 5- F 1 2.291 3, "_ C12 2 5-F 1 2.292 3,5-Cl2 2 5-F 1 2.293 2-CH3, 4-C1 2 5-F 1 2.294 2 ~ C1, 4-CH3 2 5-F 1 2.295 2-CF3, 4-CH3 2 5-F 1 2.296 2-CH3, 4-CF3 2 5-F 1 2.297--5-C1 j 2.298 2-F 1 5-C1 1 2.299 3-F 1 5-C1 1 2.300 4-F 1 5-C1 1 2.301 2-C1 1 5-C1 1 2.302 3-C1 1 5-C1 1 2.303 4-C1 1 5-C1 1 2.304 2-CH3 1 5-C1 1 2.305 3-CH3 1 5-C1 1 2.306 4-CH3. 1 5-C1 1 2.307 2-OCH3 1 5-C1 1 2.308 3-OCH3 1 5-C1 1 2.309 4-OCH3 1 5-C1 1 2.310 2-CF3 1 5-C1 1 2.311 3-CF3 1 5-C1 1 2.312 4-CF3 1 5-C1 1 2.313 2,3-Cl2 2 5-C1 1 2.314 2 > -Cl2 2 5-C1 1 2.315 2,5-Cl2 2 5-C1 1 2.316 2,6-Cl2 2 5-C1 1 2.317 3,4-C12 2 5-C1 1 (Please read first Read the precautions on the back and then fill out this page) Binding · Binding-This paper standard is universal Chinese National Standard (CNS) A 4 specifications (210X297 mm) 97

A 6 B6 V. Description of the invention) List printed by the Consumer Labor Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 2 (continued) No. · X m Y n 2.318 3,5-Cl2 2 5-C1 2.319 2-CH 3, 1 2 5 -C1 i 2.320 2-C1, 4-CH3 2 5-C1 i 2.321 2-CF3 / 4-CH3 2 5-C1 1 2.322 2-CH3, 4-CF3 2 5-C1 1 2.323--5-Me 1 2.324 2-F 1 5-Me 1 2.325 3-F 1 5-Me 1 2.326 kF 1 5-Me 2 · 327 2-C1 5-Me 1 2.328 3-C1 i 5-Me 1 2.329 4-C1 1 5-Me 1 2.330 2-CH3 1 5-Me i 2.331 3-CH3 1 5-Me 2.332 4-CH3 5-Me 1 2.333 2-0CH3 1 5-Me 1 2.334 3-0CH3 1 5-Me 1 2.335 4-OCH3 1 5 -Me 1 2.336 2-CF3 1 5-Me 1 2.337 3-CF3 1 5-Me 1 2.338 4-CF3 1 5-Μβ 1 2.339 2,3-C: 2 2 5-Me 1 2.340 2Λ-012 2 5- Me 1 2.341 2,5-Cl2 2 5-Me 1 2.342 2,6-Cl2 2 5-Me 1 2.343 3,4-Cl2 2 5-Me 1 2 · 3 “3,5-Cl2 2 5-Me 1 2.345 2-CH3, 4-C1 2 5-Me 1 2.346 2-C1, 4-CH3 2 5-Me 1 2.347 2-CF3, 4-CH3 2 5-Me 1 2.348 2-CH3, 4-CF3 2 5-Me 1 2.349--5-OCH3 1 2.350 2-F 1 5-OCH3 1 2.351 3-F 1 5-OCH3 1 2.352 4-F 1 5-0CH3 1 2.353 2-C1 1 5-0CH3 1 2.354 3-C1 1 5 -0CH3 1 2.355 4-C1 1 5-0CH 3 1 (Please read the precautions on the back before filling out this page) Binding. Threading-This paper scale is easy to use in the national standard (CNS) A 4 specifications (210X297 male dragon) 98 V. Invention description color 0)

Table 2 (Continued) Number · X 2.356 2-CH3 2.357 3-CH3 2353 U-CH3 2.359 2-OCH3 2.360 3-OCH3 2.361 4-OCH3 2.362 2-CF3 2.363 3-CF2 2.364 4-CF3 2.365 2,3-Cl2 2.366 2, "-C12 2.367 2,5-Cl2 2.368 2,6-Cl2 2.369 3,4-012 2.370 3,5-Cl2 A 6 B6 Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 2.371 2-CH3," Cl 2.372 2-C1, 4-CH3 2.373 2-CF3, "ch3 2.374 2-CH3, 4-CF3 2.375-2.376 2-F 2.377 3-F 2.373 4-F 2.379 2-C1 2.380 3-C1 2.381 4-C1 2.382 2-CH3 2.383 3-CH3 2.384 4-CH3 2.385 2-OCH3 2.386 3-OCH3 2.387 4-OCH3 2.388 2-CF3 2.389 3-CF3 2.390 4-CF3 2.391 2,3-Cl2 2.392 2,4-Cl2 2.393 2, 5-Cl2

H3H3H3H3H3H3H33333 -oc-ococococococococOCHOCHOCHOCHOCHOCHOCHCH. ^ Jr.rrr 5-5-5-5-5-5-5-5-5-05-O5-0-0-O-O33OCCCCCC I -'-'- '' y- ' — ^ Ccc 5 5 CJ 5 5 5 5 CJ 5 i TTV-CC-CVCCCCCCCFCF 555555555-5-5-5-5-5-5-5- (please read the precautions on the back before filling in this page) < This paper uses the Chinese B Family Standard (CHS) A4 specifications (210X297 gongjie) 99 A 6 B6 V. Invention description (9i) The Ministry of Economic Affairs Central Standards Bureau employee consumer cooperative printed table number 2 (performance) • X m Y 2.39 ^ 2,6-Cl2 2 5-CF3 2.395 3, ^-Cl2 2 5-CF3 2.296 3,5-C] 2 2 5-CF3 2.397 2-CH3, 2 5-CF3 2.398 2-C1 , 4-CH3 2 5-CF3 2.399 2-CF3, 4-CH3 2 5-CF3 2.400 2-CH3, U-CF3 2 5-CF3 2. ^ 01--6-F 2.402 2-F-bF 2. " 03 3-F 6-F 2. "04 kF 1 6-F 2." 05 2-C1 1 6- ^ 2. "06 3-C1 1 6-F 2.407 u-Cl 1 6-F 2Λ08 2-CH3 1 6-F 2. ^ 09 3-CH3 1 ό— 卜 2, “10 4-CH3 1 6-F 2.411 2-OCH3 1 6-F 6-F 2.412 3-OCH3 1 2.413 4-OCH3 1 6-F 2.414 2-CF3 1 6-F 2Λ15 3-CF3 1 6-F 2.416 4-CF3 1 6-F 2.417 2,3-Cl2 2 6-F 2. "18 2,4-Cl2 2 6-F 2.419 2, 5-C l2 2 6-F 2Λ20 2,6-Cl2 2 bF 2Λ21 3, "-Cl2 2 6-F 2." 22 3,5-Cl2 2 6 * F 2.423 2-CH3, '-ci 2 6-F 2.424 2 -C1, 4-C ^ 3 2 6-F 2Λ25 2-CF3, ^ -CH3 2 6-F ZΛ26 2-CH3, 4-CF3 2 6-F 2.427-6-C1 2Λ2Β 2-F 1 6-C1 2.429 3-F 1 6-C1 2.430 4-F 1 6-C1 2.431 2-C1 (please read the precautions on the back before filling in this page). This paper size is compliant with China National Standards (CNS) A4 specifications (210x297 Public *) 100 A 6 B6 V. Description of invention · Zan 2) Table 2 (Achievements) Printed number of employee consumer cooperative of Central Bureau of Standards, Ministry of Economic Affairs · X m Y n 2. ^ 32 3-C1 1 6-Cl 1 1 2.433 "Cl 1 6-C1 1 2.α34 2-CH3 1 6-Cl 1 2.435 3-CH3 5-C1 1 2.436 u-CH3 1 6-Cl 2" "37 I-OCHj ♦ 6-Cl 2.438 3-OCH3 1 6-Cl 1 2.439 "-OCH3 1 6-Cl 1 2.440 2-CF3 1 6-Cl 1 2.441 3-CF3 1 6-Cl 1 2.442 4-CF3 1 6-Cl 1 2. ^ 43 2, 3-C12 2 6-Cl i 2.444 2,4-〇12 2 6-Cl 1 2.445 2,5-Cl2 2 6-Cl 1 2.446 2, 6-C12 2 6-Cl 1 Z.kkl 3, a-Cl2 2 6-Cl 1 2. UU-8 3,5-Cl2 2 6-Cl 1 2. ^ 49 2-CH3, 4-C1 2 6-Cl 1 2.450 2-C1, 4-CH3 2 6-Cl 1 k 2Λ51 2-CF3 , A—CH3 2 6-Cl 1 2.452 2-CH3, 4-CF3 2 6-Cl 1 2.453--6-CH3 1 2.454 2-F 1 6-CH3 1 2.455 3-F 1 6-CH3 1 2.456 4-F 1 6-CH3 1 2.457 2 -C1 1 6-CH3 1 2.458 3-Cl 1 6-CH3 1 2.459 4-C1 1 6-CH3 1 2.460 2-CH3 1 6-CH3 1 2Λ61 3-CH3 1 6-CH3 1 2.462 夂 -CH3 /. 1 6-CH3 1 2.463 2-OCH3 1 6-CH3 1 2. 3-0CH3 1 6-CH3 1 2. "65 4-0CH3 1 6-CH3 1 2.466 2-CF3 1 6-CH3 1 2.467 3-CF3 1 6 -CH3 1 2.468 4-CF3 1 6-CH3 i 2.469 2,3-Cl2 2 6-CH3 1 (Please read the precautions on the back before filling in this page) This paper uses the Chinese Beta Standard (CNS) A 4 Specifications (210X297 g *) 101 034 ^ 6 A 6 B6 V. Description of the invention. (93) Printed table 2 of the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy (Continued> X m Y n 2. ^ 70 2, 4-Cl2 2 6-CH3 1 2. "71 2,5-Cl2 2 6-CH3 1 2. ^ 72 2,6-Cl2 2 6-CH3 .i 2.473 3,4-Cl2 2 6-CH3 1 2ΛΊ" 3,5-Cl2 2 6-CH3 1 2. "75 2-CH3, di-Cl 2 6-CH3 1 2.476 2-C1, 4-CH3 2 6-CH3 1 2." 77 2-CF3, 4-CH3 2 6-CH3 1 2.478 2-CH3, 4-CF3 2 6-CH3 1 2. "79--6-OCH3 1 2.448 2-F 1 6-OCH3 1 2.481 3-F 1 6-OCH3 1 2." 8 2 kF 1 6-OCH3 1 2.483 2-C1 1 6-OCH3 1 2.434 3-C1 1 6-OCH3 1 2.4S5 4-Cl 1 6-OCH3 1 2.486 2-CH3 1 6-OCH3 1 2. "87 3- CH3 1 6-OCH3 1 2.438 "-CH3 1 6-OCH3 1 2.489 2-0CH3 1 6-OCH3 1 2.490 3-0CH3 1 6-OCH3 1 2Λ91" -OCH3 1 6-OCH3 1 2.492 2-CF3 1 6-OCH3 1 2.493 3-CF3 1 6-OCH3 1 2.494 "-CF3 1 6-OCH3 1 2_" 95 2,3-Cl2 2 6-OCH3 1 2.496 2,4-012 2 6-OCH3 1 2.497 2,5-Cl2 2 6-OCH3 1 2.498 2,6-Cl2 2 6-OCH3 1 2.499 3, "-Cl2 2 6-OCH3 1 2.500 3,5-cr2. 2 6-OCH3 1 2.501 2-CH3, 4-C1 2 6-OCH3 1 2.502 2 «C1, 4-CH3 2 6 ~ OCH3 1 2.503 2-CF3, 4-CH3 2 6-OCH3 1 2.504 2-CH3," -CF3 2 6-OCH3 1 2.505--6-CF3 1 2.506 2- F 1 6-CF3 1 2.507 3-F 1 6-CF3 1 (Please read the precautions on the back before filling in this page) This paper scale is used for national standards (CNS) A 4 specifications (210X297 male dragon) 102 Economy Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Education ^ 024 ^ 6 A 6 B6 V. Description of invention · (94 Table 2 No. · (Continued) X m Y Π 2.508 4-F 1 6-CF3 1 2.509 2-C1 1 6- CF 3 i 2.510 3-C1 1 6-CF3. * 1 2.511 ά-Cl 6-CF3 1 2.512 2-CH3 i 6-CF3 1 2.513 3-CH3 1 6-CF3 1 2.5U 4-CH3 1 6-CF3 1 2.515 2-0CH3 1 .6-CF3 1 2.516 3-OCH3 1 6-CF3 1 2.517 4 -OCH3 1 6-CF3 1 2.518 2-CF3 1 6-CF3 1 2.519 3-CF3 1 6-CF3 1 2.520 4-CF3 1 6-CF3 1 2.521 2,3-Cl2 2 6-CF3 1 2.522 2 > -Cl2 2 6-CF3 i 2.523 2,5-Cl2 2 6-CF3 1 2.524 6-Cl2 2 6-CF 3 1 2.525 3, "-Cl2 2 6-CF3 1 2.526 3,5-Cl2 2 6-CF3 1 2.527 2 * CH3 / 4-C1 2 6-CF3 1 2.528 2-Cl, 4-CH3 2 6-CF3 1 2.529 2-CF3, 4-CH3 2 6-CF3 1 2.530 2-CH3, 4-CF3 2 6-CF3 1 2.531--3,5-Cl2 1 2.532 2-F 1 3,5-Cl2 1 2.533 3-F 1 3,5-CT2 1 2.534 4-F 1 3,5-Cl2 1 2.535 2-C1 1 3,5 -Cl2 1 2.536 3-C1 1 3,5-Cl2 1 2.537 4-C1 1 3,5-C12 2.538 2-CHf 1 3,5-Cl2 1 2.539 3-CH3 1 3,5-Cl2 1 2.540 4-CH0 1 3,5-Cl2 1 2.541 2-OCH3 1 3,5-Cl2 1 2.542 3-OCH3 1 3,5-Cl2 1 2.543 “-OCH3 1 3,5-Cl2 1 2.544 2-CF3 1 3,5-Cl2 1 2.545 3-CF3 1 3,5-Cl2 1 (please read the precautions on the back before filling in this page) Binding · Binding-Line. This paper scale uses the Chinese B Family Standard (CNS) A 4 specifications (210X297 public * ) 103 Ministry of Economic Affairs Printed by the Bureau of Standards and Staff Consumer Cooperative A 6 B6, description of invention · (i Table 2 (continued) No. · X m Y Π 2.5 厶 6 "CF3 1 3,5-C12 1 2.547 2,3-Cl2 2 3,5- Cl2 1 2.5ύ3 2,4-ci2 2 3,5-C12 -2f 5-C 1 7, 1 2.549 2,5-Cl2 2 2.550 2, 6-CI2 2 3,5-C1? 2.551 3,4-ci2 2 3.5- C12 3.5- C12 1 2.552 3,5-Cl2 2 1 2.553 2-CH3, 4-C1 2, 3,5-C12 1 2.554 2-C1, 4-CH3 2 3,5-C12 1 2.555 2- CF3, 4-CH3 2 3,5-C12 1 2.556 2-CH3, 4-CF3 2 3,5-C 1 2 1 2.557--3-Cl, 5-F 1 2.558 2-F 1 3-C1,5 -F 1 2.559 3-F 1 3-C1,5-F 1 2.560 UF 1 3-C1,5-F 1 2.561 2-C1 1 3-C1,5-F 1 2.562 3-C1 1 3-C1,5 -F 1 2.563 4-Cl 1 3-C1,5-F 1 2.564 2-CH3 1 3-Cl, 5-F 1 2.565 3-CH3 1 3-C1,5-F i 2.566 4-CH3 1 3-C1 , 5-F 1 2.567 2-OCH3 1 3-C1,5-F 1 2.568 3-OCH3 1 3-C1,5-P 1 2.569 4-OCH3 1 3-C1,5-F 1 2.570 2-CF3 1 3 -C1,5-F 1 2.571 3-CF 2 1 3-C1,5-F 1 2.572 4-CF3 1 3-Cl, 5-F 1 2.573 2,3-Cl2 2 3-C1,5-F 1 2.574 2,4-012 2 3-C1,5-F 1 2.575 2,5-C12 2 3-C1,5-F 1 2.576 2, 6-CV, 2 2 3-C1,5-F 1 2.577 3,4 -ci2 2 3-C1,5-F 1 2.578 3,5-Cl2 2 3-C1,5-F 1 2.579 2-CH3, 4-Cl 2 3-C1,5-F 1 2.580 2-C1, 4-CH3 2 3-C1,5-F 1 2.581 2-CF3, 4- CH3 2 3-C1,5-F 1 2.582 2-CH3, 4-CF3 2 3-C1,5-F 1 2.583--3-F, 5-C1 1 (Please read the precautions on the back before filling this page ) Installation-Line · This paper standard is universally used in China ⑽ Jia Lai_2 Gui) 104 V. Description of invention (96) Table 2 (continued) A 6 B6 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 1 number. X m Y n 2.584 2-F 1 3-F, 5-C1 1 2.585 3-F 1 3-F, 5-C1 1 2 · 536 UF 1 3-F, 5-C1 1 2.537 2-C1 1 3-F, 5-C1 2.588 3-C1 1 3-F, 5-C1 1 2.589 "C1 1 3-F, 5-C1 i 2.590 2-CH3 1 3-F, 5-C1 1 2.591 3-CH3 1 3-F, 5-C1 i 2.592 1 3-F, 5-C1 1 2.593 2-0CH3 1 3-F, 5-C1 1 2.594 3-0CH3 1 3-F, 5-C1 1 2.595 4-OCH3 1 3-Ff5-C1 1 2.596 2-CF3 1 3-F, 5-C1 1 2.597 3-CF3 1 3-F, 5-C1 1 2.598 4-CF3 1 3-F, 5-C1 1 2.599 2, 3-C! 2 2 3 -F, 5-Cl 1 2.600 2, kC \ 2 2 3-F, 5-C1 1 2.601 2, 5-Cl2 2 3-F, 5-C1 1 2.502 1, 6-CI2 2 3-F, 5- C1 1 2.603 3,4-Cl2 2 3-F, 5-Cl 1 2.604 3,5-C12 2 3-F, 5-C1 1 2.605 2-CH3, 4-C1 2 3-F, 5-Cl 1 2.606 2-Clf 4-CH 3 2 3-F, 5-C1 1 2.607 2-CF3, 4--CH3 2 3-F, 5-Cl 1 2.608 2 " CH3 / 4-CF3 2 3-F, 5-C1 1 2.609--3, 5,6-F3 1 2.610 2-F 1 3,5,6-F3 1 2.611 3-F 1 3,5,6-F3 1 2.612 4-F 1 3,5,6-F3 1 2.613 2-C1 1 3,5,6-F3 1 2.614 3-C1, 1 3,5,6-F3 1 2.615 4-C1 1 3,5,6-F3 1 2.616 2-CH3 1 3,5,6-F3 1 2.617 3 -CH3 1 3,5,6-F3 1 2.618 4-CH3 1 3,5,6-F3 1 2.619 2-0CH3 1 3,5,6-F3 1 2.620 3-0CH3 1 3,5,6-F3 1 2.621 4-0CH3 1 3,5,6-F3 1 (Please read the precautions on the back before filling in this page) Install & machi. Thread _ • {This paper size uses the Chinese National Standards (CNS) A4 specifications (210X297 public goods) 105 Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, such as 4 Gu A 6 B6 V. Invention description. Ming (97) Table 2 (Mine) No. · X m Y n 2.622 2-CF3 1 3, 5 , 6-F3 1 2.623 3-CF3 1 3,5,6-F3 1 2.624 “CF3 i 3,5,6- ^ 3 1 2.625 2,3-Cl2 2 3,5,6-f3 1 2.526 2, 4 -(^ 2 2 3, 5,6-F3 1 2.627 2,5-Cl2 2 3,5,6-F3 1 2.628 2,6-Cl2 2 3, 5,6-F3 i 2.629 3, "-Cl2 2 3r 5,6-F3 1 2.630 3,5-Cl2 2 3,5,6-F3 1 2.631 2-CH3, 4-C1 2 3,5,6-F3 1 2.632 2-Cl, 4-CH3 2 3,5,6-F3 1 2.633 Z-CF], "-CH] 2 3,5,6-F3 1 2.634 2-CH3, 4-CF3 2 3,5,6-F3 1 2.535--3, 5- (CH3) 2 1 2.636 2-F 1 3, 5- (CH3) 2 1 2.637 3-F 1 3,5- (CH3) 2 1 2.638 4-F 1 3,5- (CH3) 2 1 2.639 2-C1 1 3,5- (CH3) 2 1 2.640 3-C1 1 3,5- (CH3) 2 1 2.641 4-Cl 1 3,5- (CH3) 2 1 2.642 2-CH3 1 3,5- (CH3) 2 1 2.643 3-CH3 1 3,5- (CH3) 2 1 2.644 4-CH3 1 3,5- (CH3) 2 1 2.645 2-OCH3 1 3,5- (CH3) 2 1 2.646 3- OCH3 1 3,5- (CH3) 2 1 2.647 4-OCH3 1 3,5- (CH3) 2 1 2.648 2-CF3 1 3,5- (CH3) 2 1 2.649 3-CF3 1 3,5- (CH3 ) 2 1 2.650 4-CF3 1 3,5- (CH3) 2 1 2.651 2,3-Cl2 2 3,5- (CH3) 2 1 2.652 2,4-01 /. 2 3,5- (CH3) 2 1 2.653 2,5-Cl2 2 3, 5- (CH3) 2 1 2.654 2,6-Cl2 2 3,5- (CH3) 2 1 2.655 3 > -Cl2 2 3,5- (CH3) 2 1 2.656 3 , 5-Cl2 2 3,5- (CH3) 2 1 2.657 2-CH3, 4-C1 2 3,5- (CH3) 2 1 2.658 2-C1, 4-CH3 2 3,5- (CH3) 2 1 2.659 2-CF3, 4-CH3 2 3,5- (CH3) 2 1 (please read the precautions on the back before filling in this page) Specifications (210X297 g *) 106 V. Description of invention. (98) Central Standards Bureau of the Ministry of Economic Affairs Consumer Cooperative Printed Table 2 (Grade) Number · X m Y n 2.660 2-CH3, 4-CF3 2 3f 5- (CH3) 2 I 2.561--5,6- (CH3) 2 < 2.662 2-F 1 5,6- (CH3) 2i 2.663 3-F 5,6- (CH3) 2 1 2.664 4-FI 5,6- (CH3) 2: 2.665 2-C1 i 5,6- (CH3) 2 1 2.666 3-C1 1 5,6- (CH3) 2 1 2.667 "C1 1 5,6- (CH3) 2 1 2.668 2-CH3 1 5,6- (CH3) 2: 2.669 3-CH3 1 5,6- (CH3) 2 1 2.670 1 5,6- (CH3) 2: 2.571 2-0CH3 1 5,6- (CH3) 2 2.672 3-0CH3 1 5,6- (CH3) 2 i 2.673 "-och3 1 5f 6 -(CH3) 2 1 2.674 2-CF3 1 5, 6- (CH; 3) 2 1 2.675 3-CF3 1 5,6- (CH3) 2 1 2.676 "CF3 1 5,6- (CH3) 2 1 2.677 2,3-C12 2 5,6- (CH3) 2 1 2.678 2, "-C12 2 5,6- (CH3) 2 1 2.679 2,5-ci2 2 5, 6HCH3) 2 1 2.680 2 T 6-C12 2 5,6- (CH3> 2 1 2.681 3,4-ci2 2 5,6- (CH3) 2 1 2.682 3,5-C1 2 2 5,6- (CH3) 2 1 2.683 2-CH3, 4- Cl 2 5,6- (CH3) 2 1 2.684 2-Cl, 4-CH3 2 5,6- (CH3) 2 1 2.685 2-CF3, 4-CH3 2 5,6- (CH3) 2 1 2.686 2- CH3, 4-CF3 2 5,6- (CH3) 2 1 2.687--3,4- (CH3) 2 1 2.688 2-F 1 3 >-( CH3) 2 1 2.689 3-F 1 3,4- ( CH3) 2 1 2.690 4-F, 1 3,4- (CH3) 2 1 2.691 2-C1 1 3, 4- (CH3) 2 1 2.692 3-C1 1 3,4- (CH3) 2 1 2.693 4-C1 1 3,4- (CH3) 2 1 2.694 2-CH3 1 3,4- (CH3) 2 1 2.695 3-CH3 1 3, ' -(CH3) 2 1 2.696 4-CH3 1 3,4- (CH3) 2 1 This paper size is easy to use Chinese Η home sample standard (CNS) A 4 specifications (210X297 public goods) 107 A 6 B6 V. Description of invention ( ") Ministry of Economic Affairs Central Standards Bureau Beigong Consumer Cooperative Printed Table Number 2: (Grade) • X im Y Gate 2.697 2-0CH3 1 3, “(CH3) 2 2.698 3-0CH3 1 3, (CH3) 2 2.699 4-OCH3 1 3, one (CH3) 2 2.700 2-CF3 1 3, — (CH3) 2 1 2.701 3-CF3 1 3, 4- (CH3) 2 1 2.702 "-cf3 1 3, (CH3) 2 1 i 2.703 2,3-ci2 2 3, 4- (CH3) 2 1 2.704 2Λ-〇12 2 3, 4- (CH3) 2 i 2.705 2,5-Cl2 2 3, i- (CH3) 2 I 2.706 2 , 6-Cl2 2 3f 4- (CH3) 2 1 2.707 3, "-C12 2 3, 4- (CH3) 2 1 2.708 3,5-ci2 2 3, (CH3) 2 1 2.709 2 ~ CH3, 4- C1 2 3, 4- (CH3) 2 1 2.710 2-C1, 4-CH3 2 3,4- (CH3) 2 1 2.711 2-CF3 f A.-CH3 2 3,4- (CH3> 2 1 2.712 2 -CH3, 4-CF3 2 3,4- (CH3) 2 1 2.713--4,6- (OCH3) 2 1 2.7U 2-F 1 "X〇CH3) 2 1 2.715 3-F 1 k, 6- (OCH3) 2 1 2.716 4-F 1 4,6- (OCH3) 2 1 2.717 2-C1 1 4,6- (OCH3) 2 1 2.718 3-C 1 1 4,6- (OCH3) 2 1 2.719 4-C1 1 4,6- (OCH3) 2 1 2.720 2-CH3 .1 4, 6HOCH3) 2 1 2.721 3-CH3 1 4,6- (OCH3) 2 1 2.722 4-CH3 1 4,6- (OCH3) 2 1 2.723 2-0CH3 1 4,6- (OCH3) 2 1 2.724 3-0CH3 1 4,6- (OCH3) 2 1 2.725 4-OCH3 1 4, 6- (OCH3) 2 1 2.726 2-CF3 1 4,6- (OCH3) 2 1 2.727 3-CF3. 1 k, 6- (OCH3) 2 1 2.728 4-CF 3 1 4,6- (OCH3) 2 1 2.729 2,3-Cl2 2 4,6- (OCH3) 2 1 2.730 2> -Cl2 2 4,6- (OCH3) 2 1 2.731 2,5-Cl2 2 4,6- (OCH3) 2 1 2.732 2f6 -Cl2 2 4,5- (OCH3) 2 1 (Please read the precautions on the back before filling out this page) Binding · Binding-Line &Paper; Chinese Paper Standard (CNS) Grade 4 (210X297) ) 108 V. Description of the invention. (Ιοό

Table 2 (No.X Ore. 733 3,4-Cl2 734 3,5-Cl2 735 2-CH3, ^-Cl 736 2-C1, 4-CH3 737 2-CF3, 4-CH3 738 2-CH3, 4-CF3 Α6 Β6 2 Uf 6- (OCH3) 2 2 4,6- (OCH3) 2 2 Uf 6- (OCH3) 2 2 6- (OCH3) 2 2 4,6- (OCH3) 2 2 6- ( OCH3) 2 (Please read the precautions on the back before filling in this page) Pack. • 1T-Line · Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economics. The paper size is common in the National B Standard (CNS) A 4 specifications (210X297 Gonglong) 109 Table 3 A 6 B6 V. Description of the invention (1 (^ Xnv ^ M > _cc = o I CH 2-SO—CH 3 No. · X-my Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 3.001-0 -0 3.002 2'F 1-0 3.003 2-C1 1 1 0 3.004 3-C1 1-0 3.005 1-0 3.006 2,4-012 2-0 3.007 2, CH3, "-C1 2 — 0 3.008 2 * CH3 l-0 3.009 ", CH3 1-0 3.010 ^ -tert. C4H9 1-0 3.011--3-F 1 3.012 2-F 1 3-F 1 3.013 3-F 1 3-F 1 3.014 UF 1 3- F 1 3.015 2-C1 1 3-F 3-F 1 3.016 3-C1 1 1 3.017 4-C1 1 3 ™ F 1 3.018 2-CH3 1 3-F 1 3.019 3-CH3 1 3-F 1 3.020 “- CH3 1 3 »F 1 3.021 2-OCH3 -1 3-F 1 3.022 3-OCH3 1 3 * ~ F 1 3.023" -OCH3 1 3-F 1 3.024 2-CF3 I 3-F 1 3.025 3-CF3 1 3-F 1 3.026 "-CF3 1 3-F 1 3.027 2,3-Cl2 2 3-F 1 3.028 2tk-C \ 2 2 3-F 1 3.029 2f5-Cl2 2 3-F 3 ~ F 1 3.030 2,6-Cl2 2 1 3.031 3, 4-CI2 2 3-F 1 3.032 3,5-Cl2 2 3-F 1 3.033 2 -CH3, ^ -Cl 2 3-F 1 (please read the precautions on the back before filling in this page) Packing-line. Winter paper size is based on China National Standards (CNS) Grade 4 (210x297 mm) 110 02426 V. Description of the invention (L〇9 Table 3 (Continued

No. XA 6 B6 Printed by Beigong Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs 2.02k 2-C1, “-CH3 2 3-F t 3.035 2-CF3, ^ -ch3 2 3-F 3.036 2-CH3 / 4-CF3 2 3-F i 3.037--3-C1 ..1 3.033 2-F 1 3-C1 .3.039 3-F 1 3-C1 1 3.040 4 " -F 1 3-C1 1 3.041 2-C1 1 3-C1 1 3.042 3-C1 1 3-C! 1 3.043 4-C1 1 3-C1 1 3,044 2 -CH3 1 3-C1 1 3,045 3-CH3 1 3-C1 1 3.046 “-CH3 1 3-C1 1 3,047 2- OCH3 1 3-C1 1 3.048 3-OCH3 1 3-C1 1 3.049 "-OCH3 1 3-C1 1 3,050 2-CF3 1 3-C1 1 3.051 3-CF3 1 3-C1 1 3.052" -CF3 1 3-C1 1 3.053 2,3-Cl2 2 3-C1 1 3.054 2 > -Cl2 2 3-C1 1 3.055 2, 5-C12 2 3-C1 1 3.056 2,6-Cl2 2 3-C1 1 3.057 3 > -Cl2 2 3-C1 1 3.058 3,5-Cl2 2 3-C1 1 3.059 2-CH3 / 4-C1 2 3-C1 1 3.060 2-C1, 4-CH3 2 3-C1 1 3.061 2-CF3, 4-CH3 2 3-C1 1 3.062 2-CH3, 4-CF3 2 3-C1 1 3.063--3-CH3 .1 3.064 2-F 1 3-CH3 1 3.065 3-F 1 3-CH3 1 3.066 4-F 1 3- CH3 1 3.067 2-C1 1 3-CH3 I 3.068 3-C1 1 3-CH3 1 3.069 4-C1 1 3-CH3 1 3.070 2-CH3 1 3-CH3 1 3.071 3-CH3 1 3-CH3 1 (please first Read the notes on the back (Fill in this page again) Binding-Order _ Line. This paper standard is used in the B National Sample Standard (CNS) A 4 specification (210X297 public meeting) 111 A 6 B6 printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy V. Description of the invention (Working Table 3 (Mine) No. X m γ η 3.072 4-CH3 1 3-CH3 1 3'07.3 2-OCH3 1 3-CH3 I 3.07 "3-OCH3 1 3-CH3 i 3.075 4-OCH3 1 3-CH3. ·, I 3.076 2-CF3 1 3-CH3 I 3.077 3-CF3 1 3-CH3 l 3.078 i * -CF3 1 3-CH3 i 3.079 2,3-Cl2 2 3-CH3 I 3.080 2, U -Cl2 2 3-CH3 I 3.081 2, 5-C12 2 3-CH3 l 3 082 2,6-Cl2 2 3-CH3 l 3.083 3Λ-〇12 2 3-CH3 l 3.084 3,5-Cl2 2 J- CH3 l 3.085 2-CH3, 4-C1 2 3-CH3 l 3.086 2 ~ C1, 4-CH ^ 2 3-CH3 I 3.087 2-CF3, 4-CH3 2 3-CH3 l 3.088 2-CH3, 4-CF3 2 3-CH3 I 3.089--3-OCH3 I 3.090 2-F i 3-OCH3 I 3.091 3-F 1 3-OCH3 I 3.092 U—F 1 3-OCH3 l 3.093 2-C1 1 3-OCK3 I 3.094 3 -C1 1 3-OCH3 l 3.095 4-C1 1 3-OCH3 l 3.096 2-CH3 1 3-OCH3 I 3.097 3-CH3 1 3-OCH3 I 3.098 4-CH3 1 3-OCH3 1 3.099 2-OCH3 1 3- OCH3 1 3.100 3-OCH3 1 3-OCH3 1 3.101 "· OCH3 1 3-OCH3 1 3.102 2-CF3 1 3-OCH3 1 3.103 3-CF3 1 3-OCH3 1 3.104 k-CFj 1 3-OCH3 1 3.105 2,3-Cl2 2 3-OCH3 1 3.106 2,4-Cl2 2 3-OCH3 1 3.107 2,5-Cl2 2 3-OCH3 1 3.108 2,6-Cl2 2 3-OCH3 1 3.109 3 > -Cl2 2 3-OCH3 1 (please read the precautions on the back before filling in this page) Install & 112 paper size not using China B Home Sample Standard (CNS) A 4 specifications (210X297 public health) ^ 0242δ · A 6 Β6 V. Description of the invention (103 Table 3 (Grade) No. · X m Υ π Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 3.110 3,5 -Cl2 2 3-OCH3 1 3.111 2-CH3, ^-Cl 2 3-OCH3 i 3.112 2-ci, "-ch3 2 3-OCH3 .. 1 3.113 2-CF3, ^ -ch3 2 3-OCH3 1 3 . m 2-CH3, i-CF] -2 3-OCH3 1 3.115--3, CF3 1 3.116 2 ~ * F 1 3-CF3 I 3.117 3-F 1 3-CF3 3.118 4-F 1 3-CF3 3.119 2-C1 1 3-CF3 1 3.120 3-Cl 1 3-CF3 1 3.121 4-C1 1 3-CF3 1 3.122 2-CH3 1 3-CF3 'i 3.123 3-CH3 1 3-CF3 1 3.124 “-CH3 1 3-CF3 1 3.125 2-OCH3 1 3 ~ CF3 1 3.126 3-OCH3 1 3-CF3 1 3.127 4-OCH3 1 3-CF3 1 3.128 2-CF3 1 3-CF3 1 3.129 3-CF3 1 3-CF3 1 3.130 4-CF3 1 3-CF3 1 3.131 2,3-Π2 2 3-CF3 1 3.132 2, "-Cl2 2 3-CF3 1 3.133 2,5-Cl2 2 3-CF3 1 3.13 ^ 2,6-Cl2 2 3-CF3 1 3.135 3,4-Cl2 2 3-CF3 1 3.136 3,5-Cl2 2 3 -CF3 1 3.137 2, CH3, 4-C1 2 3-CF3 1 3.138 2-C1, 4-CH3 2 3-CF3 1 3.139 2-CF3, 4-CH3 2 3-CF3 1 3,140 2ΌΗ3, 4-CF3 2 3 -CF3 1 3.U1--kF i 3.142 2-F 1 kF 1 3.1'3 3'F 1 4-F 1 3.1 ^ 4 kF 1 4-F 1 3.H5 2-Cl 1 4-F 1 3.146 3 -Cl 1 4—F 1 3.H7 “-C1 1 ^ -F 1 (please read the precautions on the back before filling in this page) Pack * This paper size uses the Chinese B Family Standard (CNS) A4 specification (210X297 Gonglong) 113 -024 ^ 6 5. Description of the invention (10 present table 3 (continued)

No. XA 6 B6 Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 3. U8 2 -CH ^ 1 4-F 1 3. U9 3-CH3 t 1 kF 1 3.150 “-CH3 1 1 3.151 2-OCH3 1 kF 1 3.152 3-OCH3 1 4-F 1 3.153 V-OCH3 i 4-F 3.154 2-CF3 1 4-F 1 3.155 3-CF3 »4-F 1 3.156 U-CF2 1 1 3.157 2, 3-Cl2 2 4- F 1 3.158 2,4-C12 2 kF 1 3.159 2r 5-Cl2 2 kF 1 3.160 2,6-C12 2 F 1 3.161 3,4-Cl2 2 ^ — f · 1 3.162 3,5-Cl2 2 4-F 1 3.163 2-CH3, ^ -Cl 2 kF 1 3.164 2-C1, 4-CH3 2 kF 1 3.155 2-CF3, 4-CH3 2 4-F 1 3.166 2-CH3, 4-CF3 2 4-F 1 3.167 --4-C1 1 3.168 2-F 1 4-C1 1 3.169 3-F 1 1 3.170 Uf 1 4-C1 1 3.171 2-C1 1 4-C1 1 3.172 3-Cl 1 4-C1 1 3.173 4-C1 4 * C1 1 3.174 2-CH3 1 4-C1 1 3.175 3-CH3 1 1 3.176 4-CH3 1 4-Cl 1 3.177 2-OCH3 1 4-C1 1 3.178 3-OCH3 1 4-C1 1 3.179 ^ -OCH3 1 4-C1 1 3.180 2-CF3 1 4-C1 1 3.181 3-CF3 1 4-C1 1 3.182 4-CF3 1 4-C1 1 3.183 2,3-Cl2 2 4-C1 1 3.184 ΙΛ-CXi 2 “Cl 1 3.185 2,5-Cl2 2 4-C1 1 (Please read the precautions on the back before filling in this page) Sample Standard (CNS) A 4 specifications (210x297 g *) 114 * A 6 B6 V. Description of invention (lοθ The Central Consumer Bureau of Economy, Ministry of Economy, Employee Consumer Cooperative Printed Table 3 No. · (Continued) X m Y η 3.136 2,6- Cl2 2 4-C1 1 3.137 3> -Cl2 2 uc \ 1 3, '.38 3,5-Cl2 2 uc \. 1 3 .: 39 2-CH3, “-C1 2“ Cl L 3.190 2-Cl, ^ -CH3--2 .. 4-C1 j 3.191 2-CF3 / ^ -CH3 2 “Cl i 3.192 2-CH3, 4-CF3 2 4-C1 i 3.193--4-Me 1 3.194 2-F 1 4 -Me 1 3.195 3-F 1 4-Μβ 1 3.196 iv-F 1 4-Me 1 3.197 2-C1 1 Α-Μβ 1 3.198 3-C1 1 4-He 1 3,199 4-Cl 1 4-Μβ 1 3.200 2 -CH3 1 4-He 1 3.201 3-CH3 1 4-Μβ 1 3.202 “-CH3 1 4-Μβ I 3.203 2-OCH3 i 4-Me 1 3.204 3-0CH3 1 4-Μβ 1 3.205 4-OCH3 1 4- Me 1 3.206 2-CF3 1 4-Me 1 3.207 3-CF3 1 4-Me 1 3.208 “-cf3 1 i-Μβ 1 3.209 2,3-Cl2 2 4-Me 1 3.210 2, '-Cl2 2 ^ —Μβ 1 3.211 2,5-Cl2 2 Α-Ηβ 1 3.212 2,6-Cl2 2 4-Μβ 1 3.213 3,4-C12 2 4-Μβ 1 3.2H 3,5-Cl2 2 4-Μβ 1 3.215 2- CH3, 4-C1 2 4-Μβ 1 3.216 2-C1, 4-CH3 2 4-Μβ 1 3.217 2-CF3, 4-CH3 2 4-Μβ 1 3.218 2-CH3, 4-CF3 2 4-Μβ 1 3.219--4-OCH3 1 3.220 2-F 1 4-OCH3 1 3.221 3-F 1 4-OCH3 1 3.222 kF 1 '-OCH3 1 3.223 2-C1 1 4-OCH3 1 (please read the back first Note: Please fill out this page again) Line-This paper scale is applicable to the Chinese National Standard (CNS) A4 specifications (210X297 g *) 115 Λ6 B 6 V. Description of invention (ι〇1 Printed by Beigong Consumer Cooperatives, Central Standards Bureau, Ministry of Economic Affairs Tab. 3 No. (continued) X mrn 3.224 3-C1 1 '-OCH3 3,225 4-C1 1 4-OCH3 1 3.226 2-CH3 1 4-OCH3, 1 3.227 3-CH3 1 4-0CH3 1 3.228 “-CH3 "-OCH3 1 3.229 2-OCH3 1 4-0CH3 1 3.230 3-OCH3 1" -OCH3 1 3.231 4-OCH3 1 4-0CH3 1 3.232 2-CF3 1 "OCH3 i 3.233 3-CF3 1" -OCH3 1 3.234 4 -CF3 1 4-OCH3 L 3.235 2,3-Cl2 2 4-0CH3 1 3.236 2,4-Cl2 2 l4-〇CH3 1 3.237 2,5-Cl2 2 4-0CH3 1 3.238 2,6-Cl2 2 4- 0CH3 1 3.239 3. -Cl2 2 4-0CH3 1 3.240 3,5-Cl2 2 4-0CH3 1 3,241 2-CH3, 4.-C1 2 ^ -OCH3 i 3.242 2-C1, 4-CH3 2 4-OCH3 1 3.243 2-CF3, 4-CH3 2 4-OCH3 1 3.244 2-CH3, 4-CF3 2 ^ -OCH3 i 3.245--4-CF3 1 3.2 ^ 6 2-F 1 4-CF3 1 3.247 3-F 1 4 -CF3 1 3.2 ^ 8 4-F 1 "CF3 1 3.249 2-C1 4-CF3 1 3.250 3-C1 1 4-CF3 1 3.251 4-C1 1 4-CF3 1 3.252 2-CH3 1 4-CF3 1 3.253 3-CH3 1 4-CF3 1 3.254 4 -CH3 1 ^ -CF3 1 3.255 2-OCH3 1 4-CF3 1 3.256 3-OCH3 1 4-CF3 1 3.257 4-OCH3 1 4-CF3 1 3.258 2-CF3 1 夂 -CF3 1 3.259 3-CF3 1 ^- CF3 1 3.260 "-cf3 1 4-CF3 1 3.261 2,3-Cl2 2" cf3 1 (please read the precautions on the back and then fill out this page). · Tx_ line. This paper standard is used in beta countries. (CNS) A 4 specifications (210X297 male dragon) 116 V. Description of invention d 08) A 6 B6 Printed table 3 of the Central Bureau of Standards of the Ministry of Economic Affairs R and Consumer Cooperatives 3 Number (Yong) X m Y n 3.262 2> -Cl2 2 4-CF3 1 3.263 2,5-Cl2 2 4-CF3 1 3.264 2,6-Cl2 2 4-CF3 ..i 3.265 3,4-Cl2 2 4-CF3 1 3.266 3,5-Cl2 2 4-CF3 1 3.267 2-CH3, “-C1 2 4-CF3 1 3.263 2-Cl, ^ -CH3 2 4-CF3 1 3.269 2-CF3, 4-CH3 2 a-CF3 1 3.270 2-CH3, 4-CF3 2 4 -CF3 1 3.271--5-F 1 3.272 2-F 1 5-FI 3.273 3-F 1 5-F 1 3.274 4-F 1 5-F 1 3.275 2-C1 i 5-F 1 3.276 3-C1 1 5-F 1 3.277 '-Cl 1 5-F 1 3.273 2-CH3 1 5-F 1 3.279 3-CH3 1 5-F 1 3 .280 4-CH3 1 5-F 1 3.281 2-OCH3 1 5-F 1 3.282 3-OCH3 1 5-F 1 3.283 4-OCH3 1 5-F 1 3.284 2-CF3 1 5-F 1 3.285 3-CF3 1 5-F 1 3.286 "-CF3 1 5-F 1 3.287 2,3-Clz 2 5-F 1 3.288 2,4-Cl2 2 5-F 1 3.289 2,5-Cl2 2 5-F 1 3.290 2, 6-Cl2 2 5-F 1 3.291 3, 4-Cl2 2 5-F 1 3.292 3,5-Cl2 2 5-F 1 3.293 2-CH3, 4-C1 2 5-F 1 3.294 2-C1, 4- CH3 2 5-F 1 3.295 2-CF3, 4-CH3 2 5-F 1 3.296 2-CH3, 4-CF3 2 5-F 1 3.297--5-C1 1 3.298 2-F 1 5-C1 1 3.299 3 -F 1 5-C1 1 (please read the precautions on the back before filling in this page). Binding-Line-This paper standard is universal China National Standards (CNS) A 4 specifications (210x297) "117 ^ 024A 6 Β6 V. Description of invention continued

No. X Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 3.300 UF 1 5-C1 3.301 2-CI 1 5-C1 3.302 3-C1 1 5-C1 3.303 "-C1 1 5-C1 3.304 2_CHt 1 5-C1 3.305 3-CH3 1 5-C1 3.306 4-CH3 1 5-C1 3.307 2-OCH3 1 5-C1 3.308 3-OCH3 1 5-C1 3.309 4-OCH3 1 5-C1 3.310 2-CF3 1 5-C1 3.311 3- CF3 1 5-C1 3.312 4-CF3 t 5-01 3.313 2,3-Cl2 2 5-C1 3.3U 2 ^ -Cl2 2 5-C1 3.315 2,5-Cl2 2 5-C1 3.316 2,6-C12 2 5-C1 3.317 3, "-Cl2 2 5-C1 3.318 3,5-Cl2 2 5-C1 3.319 2-CH3, 4-C1 2 5-C1 3.320 2_C1, 4-CH3 2 5-C1 3.321 2-CF 2r 4-CH3 2 5-C1 3.322 2-CH3, 4-CF3 2 5-C1 3.323--5-Me 3.324 2-F 1 5-Me 3.325 3-F 1 5-Me 3.326 kF 1 5-Me 3.327 2- CI 1 5-Me 3.328 3-C1 1 5-Me 3.329 4-C1 1 5-Me 3.330 2-CH3 1 5-Me 3.331 3-CH3 1 5-Me 3.332 4-CH3 1 5-Me 3.333 2-OCH3 1 5-Me 3.334 3-OCH3 1 5-Me 3.335 4-OCH3 1 5-Me 3.336 2-CF3 1 5-Me 5-Me 3.337 3-CF3 1 1 1 [1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 (please read the precautions on the back before filling out this page) 装 · * ^ τ- 线 · 本Zhang Jixiao used the Chinese National Standards (CNS) A4 specifications (210X297 public splash :) 118 A 6 B6 V. Description of invention U〇) The Ministry of Economic Affairs Central Standards Bureau employee consumption cooperative printed i number 3x (mine) m Y n 3.338 4-CF3 1 5-Μβ 1 3.339 2,3-Cl2 2 5-Me 1 3.340 2, ^-Cl2 2 5-Me i 3.341 2,5-Cl2 2 5-Me 3.342 lt 6-C12 2 5- Me 1 3.343 3, "-Cl2 2 5-Me Ί 3.3" 3,5-Cl2 2 5-Me 1 2.3U5 2-CH3 ,. 4-C1 2 5-Me 1 3.346 2-C1, 4-CH3 2 5 -Me 1 3.347 2-CF3, 4-CH3 2 5-Me 1 3.348 2-CH3, 4-CF3 2 5-Me 1 3.349--5-OCH3 1 3.350 2-F 1 5'0CH3 1 3.351 3-F 1 5-OCH3 1 3.352 ^ -F 1 5-OCH3 1 3.353 2-C1 1 5-OCH3 1 3.354 3-C1 1 5-OCH2 1 3.355 4-C1 1 5-OCH3 1 3.356 2-CH3 1 5-OCH3 1 3.357 3-CH3 1 5-OCH3 1 3.358 4-CH3 1 5-OCH3 1 3.359 2-0CH3 1 5-OCH3 1 3.360 3-0CH3 1 5-OCH3 1 3.361 "-OCH3 1 5-OCH3 1 3.362 2-CF3 1 5 -OCH3 1 3.363 3-CF3 1 «. · 5-OCH3 1 3.364" -CF3 1 5-OCH3 1 3.365 2,3-Cl2 2 5-OCH3 1 3.366 2, '-Cl2 2 5-OCH3 1 3.367 2,5 -Cl2 2 5-OCH3 1 3.368 2,6-Cl2 2 5-OCH3 1 3.369 3,4-Cl2 2 5-OCH3 1 3.370 3f5-Cl2 2 5- OCH3 1 3.371 2-CH3, 4-Cl 2 5-OCH3 1 3.372 2-C1, 4-CH3 2 5-OCH3 1 3.373 2-CF3, 4-CH3 2 5-OCH3 1 3.374 2-CH3, 4-CF3 2 5-OCH3 1 3.375--5-CF3 1 (please read the precautions on the back before filling in this page) Pack; Order _ -line * This paper size is used in the National Standard (CNS) A 4 specifications (210x297) * ) 119 A 6 B6 Printed by the Consumers ’Cooperative of the Central Bureau of Standards of the Ministry of Economy V. Invention description in) 3.376 2-F 1 5-CF3 1 3.377 3-F 1 5-CF3 1 3.373 α-F: 5-CF3 _ 1 3.379 2-Ci 1 5-CF3 * 3.330 3-C1 1 5-CF3 1 1 3.381 "-C1 I 5-CF 3 ί 3.382 2-CH3 1 5-CF3 3.383 3-CH3 1 5-CF3 1 3.334 '-CH3 1 5-CF3 1 3.335 2-OCH3 1 5-CF3 1 3.386 3-OCH3 1 5-CF3 i 3.387 夂 -OCH3 1 5-CF3 1 3.288 2-CF3 1 5-CF3 1 3.339 3-CF3 1 5-CF3 1 3.390 "-CF3 1 5-CF3 1 3.391 2,3-Cl2 2 5-CF3 1 3.392 2Λ-〇12 2 5-CF3 1 3.393 2,5-Cl2 2 5-CF3 1 3.394 2,6-Cl2 2 5-CF3 1 3.395 3,4-Cl2 2 5-CF3 1 3.396 3,5-Cl2 2 5-CF3 1 3.397 2-CH3, 4-C1 2 5-CF3 1 3.398 2-CI, 4-CH3 2 5-CF3 1 3.399 2-CF3, 4-CH3 2 5-CF3 1 3 · "00 2-CH3, 4-CF3 2 5-CF3 1 3.4 01 3. "02 2-F 1 6-F 6-F 1 1 3." 03 3-F 1 6-F 6-F 1 3.404 UF 1 1 3.405 2-CI 1 6-F 6-F 1 3.406 3 -C1 1 1 3.407 夂 -Cl 1 6 ~ F 1 3.408 2-CH3 1 6-F 1 3. "09 3-CH3 1 6-F 1 3" "10 4—CH3 1 6-F 1 3.411 2-OCH3 1 6-F 1 3.412 3-OCH3 1 6-F 1 3Λ \ 3 4-OCH3 1 6-F 1 (Please read the precautions on the back before filling in this page) Pack. Thread-Table 3 (Continued) No. · X m Y π This paper standard is used in the B National Standard (CNS) A4 specification (210x29? Gongjie) 120 L024 £ 6

V. Description of the invention (llJ A 6 B6 Ministry of Economic Affairs Central Bureau of Standards Employee Consumer Cooperative Printed Table 3 No. · (Continued) X π Y n 3. ^ 14 2-CF3 1 6-F 1 3.-15 3-CF3 1 6-F 1 3. ^ 16 4-CF3 1 6-F 1 .- '3. ^ 17 2,3-Cl2 2 6-F i 3. ^ 13 2, “-CI2-· 2 6-F 1 3 . "19 2,5-ci2 2 6-F 1 3." 20 2t 6-C l 2 2 6-F 1 2Λ21 3 ·, 4-C1 2 2 6 * FI 3. "22 3,5-ci2 2 6 ~ * F 1 3. ^ 23 2-CH3, 4-Cl 2 6-F 1 3.UZk 2-C1, 2 6-F 1 3.425 2-CF3, 4-CH3 2 6-F 1 3.426 2-CH2 , 2 6 * F 1 3Λ27 Ink- 6-C1 1 3. "28 2-F 1 6-Cl 1 3." 29 3-F 1 6-C1 1 3. "30 UF 1 6-C1 1 3 伂 31 2-C1 1 6-C1 1 3. "32 3-C1 1 6-C1 1 3.433 kC \ 1 6-C1 1 3. ^ 34 2-CH3 1 6-C1 1 3.435 3-CH3 1 6-C1 1 3.436 4-CH3 1 6-C1 1 3.437 2-OCH3 1 6-Cl 1 3 · "38 3-0CH3 1 6-C1 1 2Λ39 4-0CH3 i- 6-Cl 1 3.440 2-CF3 1 6-Cl 1 3.441 3 -CF3 1 6-Cl 1 3.442 4-CF3 1 6-Cl 1 3.443 2,3-Cl2 2 6-Cl 1 3.444 2,4-Cl2 2 6-Cl 1 3.445 2,5-Cl2 2 6-Cl 1 3.446 2,6-Cl2 2 6-Cl 1 3. ^ 47 3Λ-〇12 2 6-Cl 1 3. ^ 48 3,5-Cl2 2 6-Cl 1 3Λ49 2-CH3, 4-C1 2 6-Cl 1 3.450 2-C1, 4-C H3 2 6-Cl 1 3.451 2-CF3, 4-CH3 2 6-Cl 1 (please read the precautions on the back before filling in this page) 210x297 male dragon) ί.024 ^ 6 V. Description of invention f13) A 6 B6 Printed form 3 Beigong Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 3 Indication · (Continued) XY n 3. “52 2-CH3, i-CF3 2 6-C1 3.'53--3. ^ 54 2-F 1 6-CH3 · * 1 3,55 3-F 1 6-CH3 i 3. ^ 56 U.-F 6-CH3 i 3_ "57 2-C1 1 6-CH3 # 1 3.458 3-C1 1 6-CH3 1 3.459 4-C1 1 '6-CH3 1 3.460 2-CH3 1 6-CH3 1 3. "61 3-CH3 1 6-CH3 ί 3.462 "-CH3 1 6-CH3 1 3.463 2-OCH3 1 6-CH3 1 3.464 3-0CH3 1 6-CH3 1 3.465 4-0CH3 1 6-CH3 3.466 2-CF3 1 6-CH3 1 3.467 3-CF3 1 6- CH3 3.468 4-CF3 1 6-CH3 1 3.469 2,3-C12 2 6-CH3 1 3.470 2Λ-〇12 2 6-CH3 1 3. "71 2,5-Cl2 2 6-CH3 1 3." 72 2 , 6-Cl2 2 6-CH3 1 3 · "73 3, ^-Cl2 2 6-CH3 1 3." 74 3,5-C12 2 6-CH3 1 3.475 2-CH3, kC \ 2 6-CH3 1 3.476 2-C1, 4-CH3 2 6-CH3 1 3.477 2-CF3, 4-CH3 2 6-CH3 1 3.478 2-CH3, 4-CF3 2 6-CH3 1 3.479---6-OCH3 1 3Λ48-2- F 1 6-OCH3 1 3.481 3-F 1 6-OCH3 1 3.482 4-F 1 6-OCH3 1 3.483 2-C1 1 6-OCH3 1 3.484 3-C1 1 6-OCH3 1 3.485 4-C1 1 6-OCH3 1 3.436 2-CH3 1 6-OCH3 1 3.487 3-CH3 1 6-OCH3 1 3.488 4-CH3 1 6-OCH3 1 3.489 2-0CH3 1 6-OCH3 1 (please read the precautions on the back before filling out this page) Order _ line. This paper standard uses the Chinese National Standard (CNS) f 4 specifications (210X297 mm) 122 ^ 〇242δ V. Description of the invention f14) A 6 Β6 Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Printed Table 3 Number -(Continued) X m Y n 3.-90 3-OCH3 1 6-OCH3 1 3. ^ 91 —OCH3 1 6-OCH3 3 'II 92 2-CF3 6-OCH3. 3. ^ 93 3-CF3: 6 -OCH3 2. ^ 94 1 6-0CH3 * 2. ^ 95 2,3-Cl2 2 6-0CH3 3.496 2 > -Cl2 2 6-OCH3 1 i 2. ^ 97 2,5-Cl2 2 6-OCH3 1 l 3 佂 98 2,6-Cl2 2 6-OCH3 1 i 3 · "99 3> -Cl2 2 6-OCH3 3.500 3,5-Cl2 2 6-OCH3 1 3.501 2-CH3, 4-C1 2 5-OCH3 1 2.502 2 ~ C1, "-CH3 2 6-0CH3 3.503 2-CF ^, 4-CH3 2 6-0CH3 1 3.504 2-CH3, 4-CF3 2 5-OCH3 1 3.505--6-CF 3 1 2.506 2- F 1 6-CF3 * 3.507 3-F 1 5-CF3 ▲ 3.508 4 —F 1 5-CF3 1 3.509 2-C1 1 6- CF3: 3.510 3-C1 1 6-CF3: 3.511 c-Cl 1 6-CF3 3.512 2-CH3 1 6-CF 3 1 3.513 3-CH3 1 6-CF3 i 3.5H 4-CH3 1 6-CF3 1 3.515 2 -0CH3 1 6-CF3 1 3.516 3-OCH3 1 6-CF3 1 3.517 4-0CH3 1 6-CF3 1 3.518. 2-CF3 1 6-CF3 j 3.519 3-CF3 1 6-CF3 i 3.520 4-CF3 i 6 -CF3 1 3.521 2,3-Cl2 2 6-CF3 1 «3.522 2t 4-C12 2 6-CF3 1 3.523 2,5-Cl2 2 6-CF3 1 3.524 2,6-Cl2 2 6-CF3 1 3.525 3, ^ -Cl2 2 6-CF3 1 3.526 3,5-Cl2 2 6-CF3 3.527 2-CH3, 4-C1 2 6-CF3 1 3.528 2-C1, “-CH3 2 6-CF3 1 3.529 2-CF3, 4 -CH3 2 6-CF3 1 3.530 2-CH3, 4-CF3 2 6-CF3 1 3.531-3,5-Cl2 1 (please read the notes on the back before writing this page) The scale is free to use China National Standards (CNS) A 4 specifications (210x297 mm) ^ 02426 V. Description of invention A 6 B6 Printed watch 3 by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs No.3 ((Grade) X m Y n 2.532 2 — F: 3,5-Cl2 1 3,533 3-F 1 1 3,5-Cl2 i 3.534 UF i 3,5-Cl2 1 3.535 2-C1 1 3,5-Cl2 1 2.536 3-C1 1 3,5 -Cl2 1 3.537 ύ-ci 1 3,5-Cl2 i 2.538 2-CH3 1 1 3,5-CI2 1 3.539 3-CH3 1 3,5 -C12 1 2.540 4-CH3 1 3,5-C12 1 3.541 2-OCH3 1 3,5 ~ C12 1 3.5 ^ 2 3-OCH3 1 3,5-Cl2 * 3.543 * ^-OCH3 1 3,5-Cl2 I 3.5 "2-CF3 1 3,5-C) 2 1 3.545 3-CF3 1 3,5-Cl2 1 3.546 4-CF3 1 3,5-C12 1 3.547 2,3-ci2 2 3,5-C12 i. 3 · 5 "8 1, 4-CI2 2 3,5-ci2 1 2.5 ^ 9 2,5-Cl2 2 3,5-Cl2 1 3.550 1, 6-CI2 2 3,5-Cl2 1 3.551 3,4- C12 2 3,5-Cl2 1 3.552 3,5-Cl2 2 3,5-Cl2 3.553 2-CH3, 4-C1 2 3,5-C \ 2 1 3.554 2-C1, 4-CH3 2 3,5- C12 1 3.555 2-CF3, 4-CH3 2 3,5-Cl2 1 3.556 2-CH3, 4-CF3 2 3,5-Cl2 1 3.557--3-Clf5-F 1 3.558 2-F 1 3-Cl, 5-F 1 3.559 3-F 1 3-C1,5-F 1 2.560 kF 1 3-C1,5-F 1 3.56Γ 2-C1 1 3-C1,5-F 1 3.562 3-C1 1 3-C1 , 5-F 1 3.563 4-C1 1 3-Cl, 5-F 1 3.564 2-CH3 1 3-C1,5-F 1 3.565 3-CH3 1 3-a, 5-f 3.566 “CH3 1 3-C1 , 5-F < 2.567 2OCH3 3-C1,5-F i 3.568 3-OCH3 1 3-C1,5-F 3.569 4-0CH3 1 3-C1,5-F i 3.570 2-CF3 1 3-Cl, 5-F ▲ 3.571 3-CF3 1 3-C1,5-F 1 3.572 “CF3 1 3-Cl, 5-F 1 3.573 2,3-Cl2 2 3-C1,5-F 1 3.574 2, kC \ 2 2 3-C1,5-F 1 (Please read the precautions on the back before filling out this page) · Order _ Line-This paper standard uses the Chinese National Standards (CNS) A 4 specifications (210X297 mm) 124-V. Description of invention ίll6) A 6 B6 Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperative Printed Table 3 Number · X (continued) m Y n 2.575 2, 5-Cl2 2 3-C1,5-F 1 3.576 2,6-C1 2 2 3—C1,! 2.577 3, “-Cl2 2 3-Cl, 5-F 5.575 -, 5-C12 2 3-C1,5-F 3.579 2-CH3, 4-C1 2 3-CI, 5-F 3.530 2-C 1, 4 -CH3 2 5-Cl, 5-F 3.581 2-CF3 , “CH3 2 3-C1,5-F II 3.532 2-CH3, —cf3 2 3-C1,5-F 1 3.583--3-F, 5-Cl 1 3.58u 2-F 1 2-F, 5 -C1 3.585 3-F 1 3-F, 5-C1 1 3.586 ^ -F i 3-F, 5-C1 i 3.587 2-C1 3-F, 5-C1 * 3.538 3-C1 i 3-F, 5 -C1 1 3.589 "Cl 1 3-F, 5-C1 l 3.590 2-CH3 1 3-F, 5-C1 3.591 3-CH3 1 3-F, 5-C1 1 3.592 4-CH3 1 3-F, 5 -C1 1 3.593 2-0CH3 1 2-F, 5-C1 1 3.59 "3-0CH3 i 3-F, 5-C1 3.595 4-OCH3 1 3-F, 5-C1 1 3.596 2-CF3 1 1 3- F, 5-C1 beer 1 3.597 3-CF3 1 3-F, 5-C1 1 2.598 “cf3 4 λ 3-F, 5-Ct» i 3.599 2,3-Cl2 2 -3-F, 5-C1 1 3.600 2> -Cl2 2 3-F, 5-C1 1 3.601 2,5-Cl2 2 3-F, 5-C1 1 3.602 2,6-Cl2 2 3-F, 5-C1 1 3.603 3,4-Cl2 2 3-F, 5-C1 1 3.604 _3,5-Cl2 2 3-F, 5-C1 1 2.605 2-CH3, 4-C1 2 3- F, 5-C1 1 3.606 2-C1, 4- CH3 2 3-F, 5-C1 1 3.607 2-CF3, U -CH3 2 3-F, 5-C1 1 3.608 2-CH3, 4-CF3 2 3 -F, 5-C1 1 3.609--3,5,6-F3 I 2.610 2-F 1 3,5,6-f3 1 3.611 3-F 1 3,5,6-F3: 3.612 kF A 3,5 , 6-F3 1 3.613 2-C1 3,5,6-F3 1 3.614 3-C1 1 3,5,6-F3 1 3.615 iv-Cl 1 3,5, 6-F3 1 3.616 2-CH3 1 3, 5,6-F3 1 3.617 3-CH3 1 3,5,6-F3 I 3.618 4-CH3 1 3,5,6-F3 1 (Please read the precautions on the back before filling this page) Install. Thread-This Paper standard Xiaoyong 8 Chinese standard (CNS) A4 specifications (210x297 male dragon) 125 6 Γ / ·· 42 ο2

66 AB

V. Description of the Invention (11) Table 3 (Grade) Number · X Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 3.519 2-OCH3 1 3, 5,6-F2 1 5.620 3-OCH3 i 3,5,6-F3 * 2.52! 4-OCH3 1 3,5,6-F3 1 3.522 2-CF ^ i. 3,5,6-F3 1 3.623 3-CF3 1 3,5,6-F3 1 5.62m- ^ -CF3 * 3, £, 6-F3 1 3.625 2,3-Cl2 2 3,5,5-F3 3.626 2, ^ -Cl2 2 3, 5, 6-F3 1 3.627 2,5-Cl2 2 3,5,6- r3 1 3.628 2,6-Cl2 2 3,5, 6-F3 i 3.629 3, 4-C12 2 3,5,6-F3 1 3.530 3,5-Cl2 2 3,5,6-F3 1 3.631 2- CH3, 4-C1 2 3,5,6-F3 1 3.632 2-C1, 4-CH3 2. 3, 5,6-F3 1 3.633 2-CF3f 4-CH3 2 3, 5,6-F3 1 3.634 2 -CH3, 4-CF3 2 3,5,6-F3 1 2.635--3,5- (CH3) 2 i 3.536 2-F 1 3,5- (CH3) 2 1 2.537 3-F 1 3,5- (CH3) 2 i 3.638 UF 1 3,5- (CH3) 2 1 3,539 2-C1 1 3,5- (CH3) 2 1 3.640 3-C1 1 3,5- (CH3) 2 l 3.541 U ~ C \ 1 3,5- (CH3) 2 1 2.6 ^ 2 2-CH3 1 3,5- (CH3) 2 3.643 3-CH3 II 3,5- (CH3) 2 * 3.644 “-CH3 λ Z, 5- (CH3 ) 2 1 3.645 2-OCH3 l 3,5- (CH3) 2 3.546 3-OCH3 i 3,5- (CH3) 2 1 3.647 4-OCH3 3,5- (CH3) 2 3.648 2-CF3 i 3,5 -(CH3) 2 3.649 3-CF3 i 3,5- (CH3) 2 1 3.650 4-CF3 1 3,5- ( CH3 > 2 1 3.651 2 # 3-Cl2 2 3,5- (CH3) 2 1 3.652 2 > -Cl2 2 3,5- (CH3) 2 1 3.653 2f5-Cl2 2 3,5- (CH3) 2 1 3.654 2, 6-CI2 2 3,5- (CH3) 2 1 3.655 3,4-CI2 2 3,5- (CH3) 2 1 3.656 3,5-Cl2 2 3,5- (CH3) 2 1 3.657 2 -CH3, '-Cl 2 3,5- (CH3) 2 1 3.658 2-Clf 4-CH3 2 3,5- (CH3) 2 1 3.659 2-CF3, 4-CH3 2 3,5- (CH3) 2 1 3.660 2-CH3, 4-CF3 2 3,5- (CH3) 2 1 3.661--5,6- (CH3) 2 1 (Please read the precautions on the back before filling in this page) Installation and thread. This For paper-scale use, it is in the B a home sample standard (CNS) A4 specification (210x297 g) 126 ^ 034¾¾A 6 B6 V. Description of invention (id Printed form 3 (cont.) By the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy No. · X m Y 2.062 2-F 1 5,6- (CH3) 2 3.563 2-F 1 5,5- (CH3) 2 W 1 5, 6- (CH3) 2 j. 〇〇5 2-C1 1 5,6 -(CH3) 2 3.666 3-C1 1 5,6- (CH3) 2 3.667 u-Cl 1 5, 6- (CH3) 2 3.668 2-CH3 5,6- (CH3) 2 3.669 3-CH3 1 i 5 , 6- (CH3) 2 3.570 "CH3 1 5, 6- (CH3) 2 3.671 2-OCH3 1 5,6- (CH3) 2 2.672 3-OCH3 1 5,6- (CH3) 2 3.673 U-OCH3 i 5, 6- (CH3) 2 3.674 2-CF3 1 5, 6- (CH3) 2 3.675 3-CF3 1 i 5, 6- (CH3) 2 3.676 4-CF3 1 5 , 6- (CH3) 2 3.677 2,3-Cl2 2 5,6- (CH3) 2 3.678 2,4-Cl2 2 5,6- (CH3) 2 3.679 2,5-Cl2 2 5,6- (083 ) 2 3.530 2,6-Cl2 2 5,6- (CH3) 2 2.631 3, "-C1 2 2 5,6- (CH3) 2 3.632 2,5-ci2 2 5,6- (CH3) 2 3.533 2_CH3 , "-C1 2 5,6- (CH3) 2 3.634 2-C1, 4-CH3 2 5,6 * (CH3} 2 3.635 2-CF3, 4-CH3 2 5,6- (CH3) 2 2.686 2- CH3, "-CF3 2 5r6- (CH3) 2 2.637--3,4- (CH3) 2 3.688 2-F 1 3,4- (CH3) 2 3.589 3-F 2, 4- (CH3) 2 3.690" F 1 3,4- (CH3) 2 3.691 • 2-C1 1 3, "-(CH3) 2 3.692 3-C1 1 3,4- (CH3) 2 3.693. 4-C1 1 3,4- (CH3) 2 3.694 2-CH3 1 3,4- (CH3) 2 3.695 3-CH3 1 3, (CH3) 2 3.596 4-CH3 2,4- (CH3) 2 3.697 2-OCH3 1 3, 4- (CH3) 2 3.698 3-OCH3 3,4- (CH3) 2 3.699 4-OCH3 1 3, "-(CH3) 2 3.TOO 2-CF3 1 3,4- (CH3) 2 3.701 3-CF3 k 3々 (CH3) 2 3.702 4-CF3 1 3, (CH3) 2 3.703 2,3-Cl2 2 3, "-(CH3) 2 3.704 2,"-C! 2 2 3, i »-(CH3) 2 3.705 2,5- Cl2 2 3 >-( CH3) 2 3.706 2,6-015 2 3,4- (CH3) 2 (please read the precautions on the back before filling out this page) Standard (CNS) A 4 specifications (210X297 public) 127 2. ο

66 AB V. Description of Inventions (119) The printed form 3 of the Employees ’Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs • (Continued) X m Y n 3.707 3, ^-Cl2 2 3,“-(CH3) 2 1 3.708 3,5 -C12 2 3,4- (CH3) 2 1 3.709 2-CH3, 4-C1 2 3, "-(CH3) 2 1 3.710 2-C1, 4-CH3 2 3, (CH3) 2 1 3.711 2-CF " 3, "CH3 2 3,"-(ch3) 2 1 3.712 2-CH3, 4-CF3 2 3,4- (CH3) 2 1 3 · 713--', 6- (OCH3) 2 1 3.714 2- F 1 ", 6- (OCH3) 2 1 3.715 3-F 1", 6- (OCH3) 2 1 3.716 1 ", 6- (OCH3) 2 1 J. / 1 / 2-C l 1 6- (OCH3 ) 2 1 3.713 3-Cl 1 4,6- (OCH3) 2 I 3.719 ^ -Cl 1 6- (OCH3) 2 1 i 3.720 2, CH3 1 ", 6- (OCH3) 2 1 3.721 3-CH3 1, 6- (〇Ch3) 2 1 3.722 4-CH3 1 ", 6- < OCH3) 2 1 3.723 2-0CH3 1 6- (OCH3) 2 i 3.72 ^ 3-OCH3 6- (OCH3) 2 4 3.725 4- OCH3 1 i 6- (OCH3) 2 1 3.726 2-CF3 1 6- (OCH3) 2 1 3.727 3-CF3 1 ', 6- (OCH3) 2 1 3.728 4-CF3 1 δ- (Ο0Η3) 2? 3.729 2 , 3-Cl2 2 kt 6- (OCH3) 2 1 3.730 2,4-012 2 k, 6- (OCH3) 2 1 k 3.731 2,5-Cl2 2 kt 5- (OCH3) 2 3.732 2,6-Cl2 2 4,6- (OCH3) 2 1 3.733 3 > -Cl2 2 k, 6- (OCH3) 2 1 3.73U 3,5-Cl2 2 4,6- (OCH 3) 2 1 3.735 2-CH3 # 4-C1 2 kt 6- (OCH3) 2 1 3.736 2-Cl, 4-CH3 2 ur 6- (OCH3) 2 I 3.737 2-CF3, 4-CH3 2 4,5 -{OCH3) 2 1 3.738- 2 ~ CH3, 4-CF3 2 4, 6- (OCH " 3) 2 1 (Please read the precautions on the back side #. Fill in this page) Binding-Stranding · Winter paper size universal China National Standards (CNS) A 4 specifications (210X297 public address) 128 024¾5 ^ A6 B6 V. Description of the invention Cj ^ q) α-ketocarboxylate VI is an important intermediate, especially for phenylglyoxylic acid- Synthesis of oxime ethers' och3

C = NI CH3O-CO It is used for crop protection, preferably as a fungicide (refer to European Patent EP-A 253 213 and EP-A 254 426 $. The final product I can Carboxylic acid VI reacts with 0-methylhydroxylamine or one of its acid-addition moles, and then the resulting E / Z isomer mixture is treated simultaneously or subsequently with M acid to prepare the heavy sister Z into E isomer ： (Please read the precautions on the back before filling in this page)

VII h2n ~ och3

Printed example 10 of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (Precursor) Precursor α 2 — (2-Methylbenzene Gas Methyl) Benzoic Acid This paper standard is universal Chinese National Standard (CNS) A4 specification (210x297 Centigrade)

C = 0 I OH 129 ^ 〇242δ A 6 B6 V. Description of the invention (12p Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. 160% (1.48 mol) o-cresol, 85% of 106 g are the most important A mixture of potassium hydroxide aqueous solution and 1.5 liters of dimethylbenzidine was continuously removed at the same time. The mixture was then cooled to 100 ℃, and at this temperature 195 grams (1.45 mol) of fenfe and 57 «dimethylmethan were added Acetamide. The mixture was then heated at 1001 for 15 hours, then cooled to 20-25 TC and K water was pumped twice for 2 liters each time, and then 140 liters of 38% by weight aqueous hydrochloric acid was added. The formed crystals, M The product was washed with 500 liters of water and dried. The product was purified by dissolving in 550 ml of acetone and recrystallizing by adding 3 liters of water. Yield: 85%; melting point 154 "0; M NMR (in CDCU, TMS is endorphin Standard>: 2.39 ρρ · (s · 3H); 5.38 ρρ · (s, 2H); 6.9-8.2 ppd (m · 8H). Precursor / 3 2 — (2-methylphenoxymethyl) benzoic acid Formaldehyde c = o I 0-CH3 12.5 g (0.1 mol) of sulfinyl sulfide was added dropwise to 24.3 g (0.1 mol) of 2- (2-methylbenzyloxymethyl) benzoic acid at 100 mL Rise The solution in leaven. After 20 to 25X: 4.5 hours, remove the scratches. (Please read the notes on the back before filling in this page) -Installation- The size of the paper is not to use China · Home Sample Standard (CNS) A 4 Specifications (210x297 g *) 130 A 6 B6 V. Description of the invention i22) Yield: 89%; melting point 51Ϊ :. INMR (in CDCU, TMS is internal standard): 2.4ppm (s, 3H); 3.98 ppm (s, 3Η); 5.58 ppb (s * 2H); 6.95 — 8.05 ppb (m · 8 H) ° Example 11 (according to the invention) 2- (2-methylbenzylmethyl) methyl glyoxylate

c = o I CHjO-CO (please read the precautions on the back before filling out this page). Packed. Printed by the Consumer Labor Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (¾ dry Ye bottled with 64 liters (0.9 mils) 2 Jiaya 51, add 8.6 grams (0.12 mole) of methenate. The mixture is heated to 65 C and at this temperature for 2 hours. • Add 20.5 grams (0.08 mole) of 2- (2-methylphenoxymethyl) A solution of methyl benzoate in 64 mL of dimethyl sulfoxide. The mixture was stirred at 20-25 ° C for about 15 hours. After the solvent was removed under reduced pressure * The residue was poured into ice water. Aqueous phase K Acidification of glacial acetic acid (out = 2> results in the formation of crystals · It was isolated, washed with saturated aqueous solution of krypton carbonate, water and diisopropyl ether, and dried. Yield: 77% of 2-(2-A Benzyloxymethyl) -ω-methyl-imidene B »1; NMR (in CDCU, TMS is internal standard): 2.3 ppm (s, 3H); 2.8 ppb (s, 3H); 4.4 ρρ »(Q · 2Η); 5.4 ppm (s, 2H); 6.9 -8.0 ppb (m'8H) ° order-line. This paper scale is universally applicable to China a standard (CNS) A 4 specifications (210X297 g *) 131 'two 02 cake A6 ___B6 V. Description of the invention t23) Step Ob) and (〇 Change Method 11. 1 Add 12.6 g (44 mmol) 3 · 3-dimethyl-5 · 5-dibromohydantoin to 24.1 g (79.8 Millimoles) 2— (2-methylbenzyloxymethyl) -ω-methyl-yinyi ”is a suspension in 400ml of propanol. At 20-25t! After stirring for 30 minutes, the pressure will be removed. Remove the solvent under _ and add 500 «L of methyl yeast and 40 ml of concentrated aqueous hydrochloric acid to the residue. Stir the mixture at 20-251C for 20 hours. Then remove the solvent under reduced pressure. And add 500 liters of ice-cold water to the residue The aqueous phase M dichloromethane was extracted three times with 150 ml each time, and then the combined extract M was gradually prepared to the average production rate. The result was that the viscous oil slowly crystallized. Yield: 85%. Change Method 11.2 30.2 g (0.1 mol) 2 — (2 — methyl stupyloxymethyl) ~ ω Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) — methyl At the room temperature, the sub-base acetone is added to 36 g (0.2 mol) of a 30% heavier M solution than 150 mg of formazan in 150 liter of formazan. Here at 20T: drop 19.8 g (0.124 mol) bromine in 50 «L of formazan. After the addition is complete • The mixture is stirred at 20 t for 30 minutes. Then 20 ml of splashed aqueous hydrochloric acid is added dropwise. The mixture flows again (about 651C) 30 After cooling, add 500 liters of ethyl acetate to the mixture, and then wash it with water for 2 ¾ each 100 liters. It is organically connected with «Ha2S0« Qianfeng and has strong suspicion. The crude product was purified by calendaring on 300 grams of silica gel with hexane / ethyl acetate (20: 1) as the dissolving agent. Yield: 54% (colorless crystal «). 1 HMR (in CDCU, TMS is the internal standard): 2.3 pph (s • 3H; CH3); 3.97 ppb (s * 3H; OCHs); 5.2 ppb (This paper scale uses the Chinese National Standard (CNS) A 4 Specifications (210X297 g *) 132 A 6 B6 L02426 V. Description of invention (12 ginger (please read the precautions on the back before filling in this page) s, 2H; CH2); 6.8 — 7.9 pp 丨 (m · 8H; Fang Family 霣 子) 0 * Example 12 (comparative example from the prior art «12.1) 2— (2-methyl-benzyloxymethyl) Grignard reaction of an Australian benzene with a monoimidazole (refer to the European case EP -A 280 185 > 110.8 g (0.4 mol) 2-(2-methylbenzyloxymethyl) in a 200 ml tetrahydrofuran will react with 10.4 g (0.4 ng) magnesium _ chips (turnings) The formed Grignard compound is added at -78t: dropwise to a solution of 61.6 g (0.4 mol) of formazan in 500 ml of tetrahydrofuran. After the mixture has reached 20-25 * C *, it is mixed After 15 hours, pour into 800 ml of ice water. The solution was washed with ether three times for 200 ml each time. Afterwards, the combined ether phase was washed to neutrality, dry and concentrated. Crude product_Tai analysis method in 190 M cyclohexane / ethyl acetate on silica gel (9: 1) is purified as a solvent. Yield: 37.8%. 12.2) 2- (2-methylbenzyloxymethyl) benzyl cyanogen MNaBr catalyzed reaction (Reference (US-A 4 234 739). Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. A solution of 20.5 grams (81 millimoles) of 2- (2-methylphenoxymethyl) benzyl cyanide in 80 milliliters of dichloromethane was added dropwise at 20-25C. To 19.6 ml of a mixture of 85% by weight of acetic acid and 1.09 g (0.01 mol) of sodium bromide. Then add 38.9 ml (0.95 mole) of formazan to the mixture at 40T. Then stir at this pan for 3 hours. HP LC analysis of the sample showed that the result was not 2- (2-methylphenoxymethyl) benzaldehyde glyoxylic acid methyl ester, but it was 2- (2-methylphenoxymethyl) benzenic acid with the highest yield. After adding 180 ml of water, the resulting mixture was pumped three times with digas methane. Each time the paper size was used. A family of 楳 楳 計 (CNS) A 4 specifications (210x297 g *) 133

V. Description of the invention (125) 50 liters, and then the organic phase M combined formula gradually made to the product. NMR (in CDCU, TMS is internal standard): 2.33 ρρβ (-s, 3 Η); 3.87 ppm (s * 3H); 5. 48 ppm (s * 2H); 6.83—6.01 pp * (m * 8H ) ° The present invention also provides a novel method for preparing aryl glyoxylate of formula Vila Ar — C0 — CO — 0 C Η 3 Vila

Ar * is phenyl or naphthyl, each of which may have from 1 to 4 selected from halogen alkyl, haloalkyl, alkoxy, haloalkoxy 'alkoxyalkyl, stupyl, stupyl , Benzyloxy, naphthyloxy, phenoxyalkyl, benzyloxyalkyl and naphthyloxyalkyl substituents, of which the last 7 substituents can only exist once, and can carry from 1 to 3 of the following: Halogens, alkyl groups, alkoxy groups, phenyl groups, stupyloxy groups plus as many halogens as other carbon atoms that can be substituted. Various methods for preparing aromatic cc-keto esters are described in the literature.

Angew. Cheuie 68 (1956) 430 and ibid. 94 (1982) 1,

Org. Synth. 24 (1944) 16 and J. Org. Chem. 29 (1964) 278 describe the hydrolysis of benzyl cyanide with concentrated mineral acid and conversion of the keto carboxylic acid into stupid glyoxylate, but a large amount is formed The method of by-products, especially stupyl formate: (Please read the precautions on the back before filling in this page) Printed by the Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperatives 9Γ H® /

J-rOR case special paintings multi case special paintings 0 German standard paper standard Chinese national standard (CHS) A 4 specifications (210x297 g *) 134 024 £ β Α6 Β6 V. Description of invention (12 treasures 2,708,189 and Tetrah. Lett. (1980 > 3539 reveals that the formation of benzoic acid can be substantially sleeved by adding a halide in several cases. It is also known to convert benzyl cyanide to the corresponding third butyl group by the Ritter reaction Base amine K (#Kao Huanzhou patent case EP-A 034,240) or keto N-glycosyl amide X (refer to EP-A 35,707). The two compounds can be converted into base carboxylic acid and carboxylate: (Please read the notes on the back before filling this page)

0-CN < f3—CO-CO-NH-C (CH 3) \ O '

IX

CO-CO-NH-COCH; X loaded. ≪ ^ > ~ CO ~ COOH J ffiib < Q > -cc > -c〇-och: Cool Path Ester, i 0 0 0 shuttle aldehyde la ethyl Si VI 基 _ Wufangfang has prepared the system from Yijin to a to increase the law of the law. This is what happened this time. The Ministry of Economic Affairs, Central Bureau of Standards' employee consumption cooperation du printing method is reached * It includes a) Reaction of the brewing cyanide of formula VI with hydrogen chloride and tertiary butyl methyl ether and Ar-CO-CN b) If necessary, under acidic conditions in A In the presence of leaven, I hydrolyzes the by-product of formula Vllb, aryl acetaldehyde, amine, amine, and winter paper, and uses the Chinese national standard _ 甲 槻 __7 公 *) A 6 B6 5. Description of the invention (12¾

Ar-CO-CO-HHR VI lb where R is hydrogen or carbohydrate group and c) if necessary • Hydrolysis by-product Vile arylacetaldehyde_ester dimethyl acetal 〇CH3

Ar-C-CO-OCH3 VI Ic 0CH3 We have also discovered the novel formula Vila ’of po-benoxymethylglyoxylate as an intermediate (please read the precautions on the back before filling this page)

CH3〇-C0 line · Central Ministry of Economic Affairs, Bureau of Standards, Employee Consumer Cooperative Printed in the parent's and Ya are halogen, (: 1 one (: 4- alkyl, (: 1 one (: 4- alkoxy or Trifluoromethyl;-m is an integer from 0 to 4; η is an integer from 0 to 3 · With the proviso that X 'is 2-chloro, 2-fluoro, 2-methyl, 4-methyl Group, 4-tertiary butyl, 2-methoxy or 2-trifluoromethyl and m is 0 or 1, or q 'is 2, 4-digas or 4-ambient 2-methyl and For paper size, please use the China Confined Family Standard (CNS) Grade 4 (210x297 mm) 136 ^ 02426 A6 _____B6___ 5. Description of the invention \ 28) When 2, η can be 0. Use as the starting formula VI Enzymatic cyanide can be prepared by, for example, the following methods (in which individual steps «revealed hydrocarbons have been revealed>): (Please read the notes on the back before writing this page) Order_ Substituents

jfV _ Ph-o + f + r ^ r-* Ph-O-CHz- ^ Y ^ 0-C = 0 II III c = of IV oh Substitute: A-Substitute if1!] — ► .... .......... c = oy ίΛΐ c = o 1 Cl V 1 CN VI Ministry of Economic Affairs Central Standards Bureau Beigongxiao # Cooperative prints a stupid or naphthyl group substituted or substituted by unhydrocarbon. In the first stage of this process, the phenol, phenol or naphthol of formula Π is preferably reacted with the lactone of formula n under sickle conditions [see for example Co 11.

Czech. Chen. Connun. 32 (19 & 7) 3448]. Conveniently convert the resulting o-benzyloxymethyl silanol IV into their volatile compounds V (refer to Organiku * * VEB Deutscher Verlag der Wissenschaften, 16th edition, BerlJn 1986, see page 423 under Μ) Convert it to the corresponding cyanocyanide VI (also see #Preparation Example 1, forefront should be 7, 5 and ξ). According to the method step ¢ 0 of the present invention, it is usually anhydrous in the presence of excess third butyl methyl group. * If it is necessary in the presence of eaves solvent or diluent, for example, in the general Chinese national standard (CNS) A4 specification (210X297 Mm) 137

5. Description of the invention (12j such as dichloromethane, tri-gas methane, tetra-gas methane or 1,2-dichloroethane, or in aromatic hydrocarbons such as toluene or tincture one, one or two or two dimethyl stupid ° It is better to use tertiary butylmethyl _. It is convenient to pass gasified hydrogen gas into the solution of glycosyl cyanide VI. All reactants are normally used in at least stoichiometric ratio. The following amounts are particularly good: from 2 to 20 times ; In particular, 8 to 12 times the amount of salicylic acid; from 3 to 15 times the amount of inert solvent; from 4 to 15 times the amount of methyl tertiary butyl ether. If using third butyl methyl »without dissolving cocoon, its It can also be present in a larger amount. If necessary, the reaction can also be carried out in the presence of acetic anhydride. The amount of acetic anhydride is not important * so it is convenient to use the amount of VI based on the amount of about 2 times the amount of Dong. The reaction is generally carried out at atmospheric pressure * in this case it is generally carried out at a temperature from -20 to 60 υ, especially from -5 to 301. The method according to the invention can provide arylacetaldehyde amine VII b as By-products ° If necessary, they can be hydrolyzed in the presence of acidic enzymes (step b) 'The suitable acid is preferably a strong acid · It is benzoic acid and benzoic acid. Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before writing this page) It is better to obtain the crude product mixture obtained in step ⑻ without separation or separation , Hydrolyzed in an inert eaves solvent or diluted cocoon (as mentioned in stage ⑻). The following amounts based on the amount of VI are particularly preferred in step (b): — from 3 to 10 times the amount of enzymes; — from 1 To 15 times, especially from 3 to 10 times the amount of mandelic acid or ascorbic acid. This step is also generally carried out under atmospheric pressure, and from -20 to 100C, this paper scale is commonly used in BB home sample standard (CNS) A4 specifications (210x297 Kg) 138 024¾¾ A 6 B6 V. Description of the invention (L30) Especially from 20 to 80 * C. The condition of step (b) can provide a small amount of para-aryl acetic acid The dimethyl acetal Vile is a by-product. If necessary, they can be hydrolyzed to aryl acetic acid to brew Vila. Generally speaking, hydrolysis is easy to dissolve in thin organic or thinner under acidic conditions ( As described in step ⑻> • It is preferably carried out in dichloromethane, 1.2-diethyl ethane or toluene. Reaction Specially performed in a two-phase system composed of aqueous acid and organic solvent. «Preferable acids are organic acids such as acetic acid, trifluoroacetic acid and p-methanesulfonic acid and certain acids such as ashenic acid, telluric acid and phosphoric acid. Μ Salinic acid and sulfuric acid are preferred. Normally, an aqueous solution of 2-12 dangman acid is used. The amount of _ is generally based on the amount of VI from about 10 to 500 mol%. The reaction is normally carried out at atmospheric pressure * -20 to 80C * Specially carried out from 0 to 40T as a legacy. The method according to the present invention can be carried out «successively or batchwise. When the continuous performance is carried out • pass the reactants to" e.g. tube type The order of the reactor or stirring vessel is questionable. The method according to the present invention provides arylglyoxal VIla with high yield and extremely high purity. Printed by the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling in this page) The preparation method can be successfully used to synthesize all defined aryl glyoxylic acid_VIIa * especially those Ar is phenyl or Tsai, both of which may have substituents from 1 to 4 lixiong from the following:-from 1 to 3 halogen atoms such as fluorine, chlorine, o and iodine, especially fluorine and iodine; a From 1 to 3 branched or unbranched alkyl substituents, in particular, a paper-based version of the Chinese National Standards (CNS) A 4 specifications (210x297 mm) 139 A 6 B6 V. Description of the invention (l3l) "An alkyl group such as methyl, ethyl, n-propyl, isopropyl and n-butyl; an alkyl substituent partially or constitutionally fibrillated from 1 to 3 㑩, especially an alkyl group such as fluoromethyl Group, gas methyl group, trifluoromethyl group, trichloromethyl group, 1,1,2-trichloroethyl group and pentachloroethyl group; — branched or unbranched alkoxy substituents from 1 to 3 valences, especially It is a "monoalkoxy group such as methoxy, ethoxy, n-propoxy, isopropoxy and n-butoxy; an alkoxy substituent partially or completely halogenated from 1 to 3 㑩· In particular, "one alkoxy group such as trifluoromethoxy group and three gas methyl group; a branched or unbranched alkoxyalkyl group from 1 to 3 li, especially Ci-C * -alkoxy one Ci—C · »—alkyl groups such as methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, methoxyethyl, ethoxyethyl, n-propoxyethyl and n-butoxy Ethyl; and a 1 stupidyl group, phenoxy group, benzyl group, cyanooxy group or stupid alkyl group, especially stupidoxy-Ci-c4-alkyl group such as stupidoxymethyl group and stupidoxyethyl group, Benzyloxyalkyl especially benzyloxy-Ci-C * -alkyl such as benzyloxymethyl and benzyloxyethyl, or Cyanyl alkyl especially Cyanyl-Cl-alkyl such as naphthyloxymethyl and lyoxyethyl Printed by the Employee Consumer Cooperative of the Central Bureau of Trade and Industry of the Ministry of Economic Affairs (please read the precautions on the back before writing this page). The last 7 substituents can be priced from 1 to 3 at the following price: 3 mentioned above Halogen, especially fluorine and gas, 3 alkyl groups, especially Ci—C4 —alkenyl (as mentioned above), 3 decyloxy groups, especially Ci — C4 —homoyl group (as mentioned above), 1 p-phenyl And 1 phenoxy, plus as its He can be replaced by as many halogen atoms as mentioned above (especially as mentioned above), especially fluorine and gas. # This paper scale uses the Chinese National Standard (CNS) A 4 specification (210x297 mm) 140 A 6 B6 t 〇24 Zhanwu. Description of the invention (13 ^ Specially suitable compounds Vila are those in which Ar is phenyl. • It can be substituted by alkylalkoxy, phenoxy, benzyloxy, and stupyloxymethyl, and Aromatic substituents may carry the following additional groups X and Υ buried from: a halogen such as fluorine, atmosphere, bromine and iodine • especially fluorine and gas; — branched or unbranched one. An alkyl group such as methyl Group, ethyl, isopropyl and n-butyl * especially methyl and ethyl; — branched or unbranched (^ — C4-alkoxy such as methoxy, ethoxy, 1-methyl. B Oxygen, n-propoxy and n-butoxy; a trifluoromethyl group. The best aryl glyoxylic acid VIIa can be found in Table 1. The formula VI la 'post a stupid oxymethylglyoxylate is novel (please read the precautions on the back before filling this page).

X 'and Y in the printed form of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs are each halogen, "-"-alkyl, "-(: 4-alkoxy or trifluoromethyl; m is an integer from 0 to 4 ; Η is an integer from 0 to 3, with the proviso that X 'is 2-chloro, 2-fluoro, 2-methyl, 4-methyl, 4-tertiary butyl, 2-methoxy Or 2-trifluoromethyl and m is 0 or 1, or X 'is 2,4-dihydroxy or 4-chloro-2-methyl. The paper standard is based on China National Standards (CNS) A 4 specifications ( (210x297 disciple) 141 024 pale A 6 B6 5. Description of the invention (33)

And when m is 2, η may be 0. The aryl glyoxylates Vila and Vila ’are important intermediate products. They are especially suitable for the synthesis of stupid glyoxylic acid. E—oxime ether I OCHj

C = M I CH3CKCO It is used for crop protection, preferably as a fungicide (refer to European Patent EP-A 253,213 and EP-A 254,426). The final product I can be prepared by reacting aryl glyoxylate Vila, if it is a crude product, with a mixture of dimethyl acetal Vllb, and 0-methylhydroxylamine or one of its acid addition salts , The E / Z isomer mixture formed is treated with acid at the same time or subsequently, for the substantial heavy sister Z to E isomer:

： Η ^ ίΓ Is0 CH30-CO H2N ^ OCH3

C = N-0CH 3 CH3O-CO (Please read the precautions on the back before filling out this page)

VII Printed anterior body 1 of the Employee's Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 1 1 Yi Caijia cyanocyanine paper standard used in China National Standards (CNS) A 4 specifications (210X297 mm) 142 A6 B6 V. Description of invention (13 j 〇9 c = o 127 g (0.661 $ ear) 1-naphthol, 36 g (0.73 mol) sodium cyanide, 0.2 g (0.6 mol) tetrabutyl bromide, 200 mol A mixture of water and 300 liters of 1,2-dioxane was stirred at a high speed for 2 hours, maintained at 40 t: K by cooling with Μ ice water, and gradually made and similar to the precursor 7. Yield: 55%; Melting point: 90 — 9H. Precursor 艚 2 2 — Benzyl benzyl alcohol (please read the notes on the back before filling this page)

Installation · Printed by Beigong Consumer Cooperative of Central Bureau of Standards of the Ministry of Economic Affairs, 15.5 g (0.13 guar) sulfinic acid at 0 to 5 t: dropwise to 19.8 g (0.1 mol) 2-Benzy Benzoic acid, 10.3 g (0.13 mol) mixture of pyridine and 100 liters of B "reaction mixture at 20-25t: stirring for about 15 small bites, and then gradually made as usual. Yield: 23.4 g crude product precursor 3 2 _phenylbenzyl

This paper uses the National B Standard (CNS) 4 specifications (210X297 g *) 143 V. Invention. Description (13δ) 23.4 g (0.108 mol) -2-Benzyl benzyl chloride, 190 liters A mixture of two gaseous methane, 5.8 g (0.119 mol) sodium cyanide, 0.1 g (0.3 mol) tetrabutylammonium bromide and 75 liters of water was stirred at 20 * C (ice bath) for 3 hours. Wash in water and gradually make it as usual. Yield: 89% ° Example 1 3 (according to the present invention) 2 — (2-methylbenzyloxymethyl) methylbenzyl glyoxylate (please read the precautions on the back before filling this page)

Suspend 60 grams (0.2 mole) of 2 cyanogen in a mixture of 150 dianhydride. • Pack gaseous hydrogen chloride (2-methylbenzyloxymethyl) -benzyl cyanide-printed. Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Prepared by stirring at 20-25C for 10 hours and then depressurizing the aqueous phase with 300 ml of 50 liters each time and then acid to the residue for 15 hours. Separate the phase of methyl tertiary butyl. The mixture was cooled through and saturated with M, stirred for about 20 hours, and the solvent was removed. Methyl tertiary butyl soil shrinkage. After adding 120, the mixture was mixed with 20 g of organic conjugated ether and -5 Ό, and then removed for cooling, and then added 50 μl of the residue. The residue was dissolved in ether and extracted. Ether milliliters of dimethicone at a high speed of 20-M concentrated mineral acid (0.2 should not be from -5 to .β, then methanol. Mix 200 liters of the phase and then stir with hydrogen chloride and 40 mmol of water to dissolve the ear) B 5 Mixture of alcohol and water under C, and wash 3 litres of salt mixture and water on paper. Use Chinese National Standards (CNS) Grade 4 (210X297 g *) 144

L024S6 V. Description of the invention (I3 order washing, then dry and clean the box. Yield: 59 g of crude product which (according to gas chromatography) contains 84 mol% of the desired product., 2— (2 — A 1H-HMR of methyl stupid glyoxylate (in CDCU; TMS is internal standard): 2.3 ρρ · (s, 3H): 3.80 ppm (s, 3Η); 5.40 ppb (s, 2Η); 6.90 pphi (t * 2H); 7.15 ppm (t * 2H); 7.45 ppm (t · 1H); 7.65 ppm (t, 1H); 7.80 ppm (d, 2H). Example 14 (according to the invention ) 1 —Methyl naphthalene glyoxylate '(Please read the precautions on the back before filling this page)

CH 3〇-CO installed · Pass anhydrous argon argon to saturate 30 g of a mononaphthalene cyanide (precursor δ), a mixture of 17 g of acetic anhydride and 80 l of methyl tert-butyl ether at the same time 0- 5t: Under stirring. The mixture was then stirred at 20-25C for 10 hours, during which a homogeneous solution was formed. Add 200 ml of formazan and reflux the mixture for 10 hours, then concentrate under reduced pressure. The residue was dissolved in 300 liters of methyl tert-butyl ether, and then the solution M was washed twice with 200 liters of water each time, and finally dried and concentrated. Yield: 34 g of oily mixture • It (according to gas chromatography) contains 58 mol% of the desired product and 32 mol% of 1-methyl naphthalene glyoxylate dimethyl acetal. * Example 15 This paper is used in China National Standard (CNS) Grade 4 (210X297mm). Printed by the Ministry of Economic Affairs, Central Standards Bureau, Beigong Consumer Cooperative Co., Ltd. 145, 02426 A 6 B6 5. Description of the invention) 1 —Lianben glyoxylic acid methyl ester

Hydrogenated anhydrous hydrogen was introduced into a mixture of 20 g (97 μmol) saturated 2-benzylbenzyl cyanide, 9.9 g (97 μmol) acetic anhydride and 180 μl methyl tert-butyl ether at the same time -Stir at 5C. After the mixture is warmed to 20C, add 55 ml of formazan. The mixture was stirred at 20-251C for 72 hours, after which the solvent was removed. The residue was dissolved in dichloromethane, and then the organic phase K was washed with water and gradually prepared as usual. Yield: 17.4 grams. (Please read the precautions on the back before writing this page) Printed by Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs This paper scale is used in China National Standard (CNS) Grade 4 (210X297) * 146

Claims (1)

Six 'patent application model iV-ί Α7 Β7 C7. A D7 ^ fy i i> >. Ask Λ., I A method for preparing phenylglyoxylic acid of formula 1-E-oxime silver carp In the formula, X and Y are each halogen, Ci-Cd-alkylfluoromethyl; m is from η, which includes a) make incense I C < L-alkoxy or three integer from 0 to 4; 0 to 3 Integer; Use a base selected from alkali koji hydroxide or alkali alkaloid fermented salt, in the presence of aromatic hydrocarbon or fermented diluent, 0 to 100 t: below, convert the phenol into phenate II b) Mix this Phenolate and lactone of formula I * 29 : = 〇III (Please read the precautions on the back of KI before filling in the Luan page) Armored 4 (210X297 Public Broadcasting) printed by the Central Standards Bureau of the Ministry of Economic Affairs, .0242¾ VI. Applying for Patent Fan® A7 B7 C7 D7 c) By steaming Remove the diluent and react the molten mixture at 50 to 250 υ, and d) Dissolve the still molten liquid in water and acidify to a pH of less than 7, and then convert it into Formula IV 2-stupid gas Methyl Benzoic Acid IV) K phosgene or sulfenyl chloride is converted into the corresponding formula V 2 -dioxymethylbenzyl chloride at 0 to 100 TC in the conventional manner V and f) Reaction of 2-dioxymethylbenzyl chloride V at 0 to 400 υ with alkali gold contact or earth test gold cyanide, if necessary in the presence of hydrocyanic acid > and g) Formula VI2-Phenoxymethylbenzyl cyanide reacts with methanol in the presence of -80 to 80¾ and the presence of inorganic acid T4C210X297 () Please read the precautions on the back and fill in this hundred) r ~ A7 2〇24 B7 W C7 D7 6. Patent application h) If necessary, the by-product of the ketal carboxylate dimethyl acetal of Vllb in the presence of 0 to 100 c and chloroform acid ▽ lib and if necessary, the by-product of α-keto f carboxyglycosamine of formula Vile is subjected to step < 80 In the Vile formula, R is a radium or a sleeping group. • or i) Reaction of o-benzylmethyl stearate of formula Va with dimethyl sulfonate in the presence of a base of 0 to 120 Ό and alkali metal yeast (please first Read the precautions on the back and fill in this page) • Install ·-hit · • Green. Printed by the Central Bureau of Standards of the Ministry of Economic Affairs f 4 (210X297; C = 0 I ο-r Va 6. Patent application area A7 B7 C7 D7 where R is Ci — C 4 — comprehensive base · J) The formula of mixed Via / 3 / 3-ketosulfinic Via C = 0 I CH2-SO-CH3 with chlorine or bromine halogenating agent, under 0 to 80 it, and this mixture is reacted with formazan in 0 to 100 it and without the presence of alkyd, k) and then formed Formula of Vila 2-dioxomethyl glyoxylic acid methyl ester vili @ 式 V I lb 的 acetal CH3O-C0 OCH; OCH. Vllb ................................... π ...... ......... St ........................ ^ ........ ^ .................. Fate (please read the precautions on the back before filling in the Luan page) Printed by the Central Bureau of the Ministry of Economic Affairs ¾ or a mixture of compounds VII a and VI ib Inverted with Ο-methylhydroxylamine or one of its hydrochloric acid or sulfate, and at the same time 74 (210X297 g; ¥) 4 ^, 024¾¾ Six, apply for a patent scope a A7 B7 C7 D7 or after -20 to 100 1C K without acid treatment. 2. A method for preparing 2-dioxymethylbenzoic acid of formula IV iT \ y- ^ cH2Xp IV c = o I CH where X and Y are each halogen, "-" alkyl, Ci-C4-alkyl Oxygen or trifluoromethyl; m is from η is an integer from 0 to 4 which includes a) M hydrocarbons; an integer from 0 to 3, selected from the sickle of alkali gold or hydroxide or fermented gold salt, In the presence of aromatic or fermented diluent, 0 to 100 1C, convert formula E phenol into phenate II ............................... ........................... Pretend ..................... ......... hit .............................. (please read the notes on the back first (Fill in this page again) b) Convert this phenate to lactone of formula Π [ 0-c = c III A4 (210X297 or 'A') < 'Α ο λ r λ- A7 B7 C7 D7 VI. Application for a patent c) c) The diluent is removed by steaming and the mixture in the melt Invert from 50 to 250 ¾, and d) Dissolve the melt in water while it is still liquid and acidify to pH less than 7. a—A method for preparing ortho-substituted benzyl cyanide of formula VI, which includes reacting benzyl chloride of formula V at 0 to 40 1C with gold tester or alkaline earth metal cyanide * if necessary in the presence of hydrocyanic acid The next reaction (please read the precautions on the back before filling out this page). Install V c = o I c \ In the formula, X, Y, m and η have the meaning specific to item 1 of the patent application. <-A method for preparing acetyl chloride of formula V, including the use of carboxylic acid of formula IV c = o IV line under 0 to 100 υ * reaction with phosgene or sulfenyl chloride to prepare CB species of ester acid after the base of the Ministry of Economic Affairs Central Standards Bureau printed f 4 (210X297 public) A7 B7 C7 D7 CN ^ 024 ^ 6 VI. Patent application ® Vila where X and Y are each halogen, Ci-Cd-alkyl, Ci-C4-alkoxy or trifluoromethyl; in is an integer from 0 to 4; η is an integer from 0 to 3 * which includes a) the reaction of o-benzyl methyl benzyl cyanide of formula VI with formazan in the presence of -80 to 80Ό in the absence of benzoic acid, VI b) if necessary, at 0 Cleavage formula Vllb copper carboxylate dimethyl acetal by-product in the presence of 100 TC and hydrogen chloride, (please read the precautions on the back before filling this page) Vllb Printed by the Central Standards Bureau of the Ministry of Economic Affairs and, if necessary, the step VIa Ic (a) treatment of carboxylammonium by-products and then subject to Z A 4 (210X297 public) '〇 ,: 4 Dipped A7 B7 C7 D7 Six 2. Apply for a patent Vile & where R is hydrogen or acetyl. Method for preparing α-keto carboxylic acid ester of formula Vila Vila where X and Y are each haloalkyl-C alkoxy or trifluoromethyl; m is an integer from 0 to 4; η is an integer from 0 to 3, which includes a) Phenoxymethyl stearate and dimethyl sub-crushed in the presence of 0 to 120 1C and in the presence of lithium metal fermented lithium | ......................... .....................- «................. R ............. ........... ir ..................... sf ( Please read the precautions on the back before filling out this page) Economy Lang Zhongxing Rubbing and Printing Bureau f 4 (210X297 Gong 4Π .4¾¾ Six. Patent application area A7 B7 C7 D7 b) At 0 to 80t • Add halogenating agent of chlorine or bromine to formula Via / 3 / bisyl sub-product Via and c) This mixture is reacted with formazan in the presence of mineral acid from 0 to 100 ° C. 7. A method for preparing E-oxime ether of phenylglyoxylate of formula I ch3〇-c〇 where X and Y are each halogen, "-C4-alkyl, Ci-CA-alkoxy or fluoromethyl; m is an integer from 0 to 4; η is an integer from 0 to 3 , Which includes the formula Vila phenylglyoxalate ......................................_ .. ............. pretend ........................ fight ... ... ί ................. Line (please read the precautions on the back before filling the nest page) Printed by the Central Bureau of Standards of the Ministry of Economic Affairs ¾ A 4 (210X297; ^ 024¾¾ A7 B7 C7 D7 VI. Patent application c = o / I-CH 3O-CO or acetal of stupid glyoxylate of formula Vllb X c. I och3 CH jO " CO (please read the precautions on the back before writing this page) or the mixture of the compounds Vila and Vllb reacts with O-hydroxylamine or one of its hydrochloric acid or sulfuric acid, and simultaneously or afterwards K inorganic acid treatment at -20 to 100 C. a—A method for preparing the aryl glyoxylate of formula VI Id • Ar — C0 — CO — 0 C Η 3 VII d where the formula • Central Ministry of Economics and Trade Central Printing Agency ¾ Ar is phenyl or naphthyl , Each of which may have from 1 to 4 selected from halogen, Ci-CA alkyl, (: broad "haloalkyl, alkoxy, Ci-C * haloalkoxy, C: i-C4 alkoxy Substituents for alkyl, stupid, stupid, benzyloxy, naphthyloxy, phenoxy-Ci-C * -alkyl, benzyloxy-“-C4-homoyl and naphthyloxy-Ci-Cr alkyl • Among them, the last 7 substituents can only exist once and can carry from 1 to 3 lower ones. Arrival: halogen, Ci-“-alkyl, Ci-Cr alkoxy, stupyl, stupidoxy, plus If there are other halogen atoms with as many carbon atoms as possible, including 4-4 f4 (210X297 ^ '4f) A7 B7 C7 D7 6. Patent application ® a) The acyl cyanide of formula Vl.b is reacted with hydrogen chloride and third butyl methyl ether at -20 to 60C hr—CO—CN V lb b) If necessary, the byproduct Vile aryl group Acetaldehyde acetamide hydrolyzes Ar—CO—CO-HHR Vile in the presence of hydrogen acid or sulfuric acid and formazan in the presence of -20 to 100 * 0 where R is hydrogen or acetoxy • and c) if necessary * in -20 to 8 Under 〇υ, hydrolysis by-product Vllf aryl glyoxylate dimethyl acetal 0CH3 I Ar — C — CO — 0C H a VII fi OCH (please read the precautions on the back before filling this page) • Install · • Hitting • • Printed U f 4 (210X297 province) by the Central Standards Bureau of the Ministry of Economics