TW304158B - - Google Patents

Description

304158 A7 B7 V. Description of the invention (1 y Background of the invention, weeds will cause huge global economic losses due to lower crop yields and lower crop quality. For the United States alone, agricultural crops need to compete with hundreds of weeds. ^ Despite the fact that herbicides are commercially available today, crop damage caused by weeds still exists. Accordingly, research is needed to produce novel and more effective herbicides. Certain heterocyclic phenyl herbicides are known (see, for example, W〇 85 / 〇1939, 77938-Α2 and US 5,356,863). However, none of these gazettes disclose heterocyclic phenyl compounds substituted with υ ^ Sanken-2,4,6-trione groups. Candidiasis 1,3 , 5-Tri-Pen · 2,4,6_triones are described in US 4,876,253 and the '927,82W Dan patent does not disclose, any heterocyclic styl substituted 3,5-tri_-2,4 , 6-trione. Furthermore, the patentee did not disclose any herbicidal utilization of its compounds. Mouth EP 64〇6〇〇_A1 and US_4, Chuan, 797 revealed the herbicide 13 5_ 三 whistle-2 , 4,6-Di Si. But these male Hao Pei ancestors-Yi Shou Bao did not disclose any 1,3,5-di? 1 well-2,4,6-tri§ ^ compounds substituted by any heterocyclic stupyl groups Ancient :: Ta's Department provides _ kinds of compounds that are used to control unwanted plant species are effective. The Ministry of Economic Affairs Central Bureau of Standards and Technology Employees Consumer Cooperative printed another object of the present invention ^ I,. Methods for controlling unwanted plant species 0 These and other objectives of the present invention by Jiang Shi will become clearer from the following detailed description. 0 tgg overview The present invention describes a single agent that can be used as a poor rabbit, qiongma, etc. <1- (3-heterocyclic phenyl) -Zhan Sangeng_ The paper standard Lai Guanguan A7 B7 V. Description of the invention (2 y. 2,4,6-oxyl or thiotrione compound ^, The 1- (3-heterocyclic phenyl) -blue-trip-well-2,4,6-oxy or thiotriphenyl compound of the present invention has the structural formula I:

R

1 ^-(please read the notes on the back before filling this page) YA A] R, haloalkyl, Crc4 alkoxy, CrC # haloalkoxy or S (0) mR2; m is 0, 1 or Integer of 2; heart is ^-~ alkyl or CrC4 haloalkyl; R is hydrogen, CrC6 alkyl 'C2-C12 alkoxyalkyl, C3-C12 alkylcarbonylalkyl, C3-C12 haloalkylcarbonylalkyl, C3-C12 alkoxycarbonylalkyl, C3-C12 haloalkoxycarbonylalkyl, C3-C6 alkenyl, C3-C6 alkynyl, alkali metal, printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economy Halogen, alkyl, CrC4 alkoxy or Crq halogen alkoxy substituted phenyl, or optionally one to three halogen, cvc4k group, &lt; ^-(: 4 alkoxy or (^-(^ haloalkane Oxygen substituted benzyl; R! Is hydrogen, C3-C6 alkenyl, C3-C6 alkynyl, cyano, optionally via one or more halogen atoms' or a cyano group, c (o) r3, c ( w) r4, 〇c (o) r5, CH20C (0) R5, or4, ch2or4 -5- The paper size is applicable to the Chinese National Standard (CNS) A4 specifications (210 X 297 mm) A7 B7 3u4158 (3 or CR0 (OR7) 2 bases or one depending on the situation γ brotherhood-to three teeth

CrC4 burned group, ίν (: 4 alkoxy or '14 4 cheng and ci C4 halooxy substituted phenyl substituted CrC12 alkyl; or optionally-to three teeth, crc4 alkyl,% Alkyloxy or Ci-C ^ Huanxuan • Pyryl substituted phenyl; R3 is OH, 0R8, SR8 or NR9R1〇; W is Ο, NOR9, NCOR9 or nnhconh2; R4, 115 and 116 are each hydrogen, CrC4 Alkyl or Cl-C4_alkyl; R * 7 is C1-C4 alkyl;

Rs is optionally C〗 -C4 alkoxy, Ci-C: 4 alkylthio, halogen, hydroxy, C3-C6 cycloalkyl, furyl or optionally one or more halogen, cyano, nitro 'CrC4 alkyl, Ci_c4 south alkyl, CrC4 alkoxy or Ci-C: 4 halogenated alkoxy substituted phenyl substituted morphology; optionally CrC4 alkoxy, halogen, (: factory-centered cycloalkyl Or optionally substituted by one or more halogen 'cyano, nitro, Cl-c4 alkyl, cv C4 haloalkyl, Crq alkoxy or phenyl substituted haloalkoxy phenyl c6 alkenyl; c3-C6 alkynyl substituted with alkoxy or halogen as appropriate; C3-Cy_t burned; N = C (R4R5); or metal test, earth-storing metal, magnesium, copper, zinc, aunt, Silver, nickel, press, organic press cation; R9 and R10 are hydrogen, CrC6 alkyl, -6- Ben Newton scale suitable for financial Guanjia County (CNS) A said grid (210 &gt; &lt; 297 public epidemic- ------- Zhuangyi ------. 玎 ------ A ί {(please read the Vi matters on the back first and then fill out this page) Employee Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs Printed ^ 04158 \ Ί Β7 5. Description of the invention (4 ·) '· One or more halogens, cyano, Radical, alkyl, (ν &lt;: 4 haloalkyl, cvc4 alkoxy or Ci-q halogenated alkoxy substituted; or optionally one or more halogen, cyano, nitro, alkyl, Alkyl, (^-(^ alkoxy or crc4 phenyl substituted by alkoxy; Q is selected from A3 A3, human j NN K11 \ ANN y ~ \-\ / N = N r12 i A4 R12 ' Q1 Q2 Q3 -R, (Please read the precautions on the back before filling out this page) Pack. Order 〇

And ί 1 Ν = {• N N ^ R11

R 13 and N 八 N ~ 11 M R, • R, 12 Q5 Q6 Printed by the Ministry of Economic Affairs, Central Standard Falcon Bureau Negative Work Consumer Cooperatives • N 八 Zi R 13

R 12 11 H Q7

M • N N

R 11 R Q8 12 〇 N-N H, Q9

R 12 The permanent scale of this paper is applicable to the Chinese National Standard Falcon (CNS) A4 specification (210; &lt; 297 mm) V. Description of invention (5 Μ Β7

This paper scale is applicable to the Chinese National Standard (CNS) Α4 specification (2 丨 ΟΧ 297mm) A7 B7 V. Invention description (6

The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (2Ι〇κZ97mm) Α7 Α7 Printed by the Employee Consumer Cooperative of the Central Department of Economics of the Ministry of Economic Affairs 5. Description of the invention (7 ·) '·

Rjl and R! 2 are respectively nitrogen, C alkyl substituted with one or more halogen atoms as appropriate, or C3_C6 cycloalkyl substituted with one or more halogen atoms as appropriate, and when RnKRu and its attached When the connected atoms are combined together, it may represent a 4- to 7-membered saturated or unsaturated ring with Ο, S (0) r4 N optionally inserted by one to three methyl groups or one or more atom atoms; R13, r14 and r15 are each hydrogen, Ci_c3 alkyl or Ci_c3 haloalkyl; Κ · 16 is hydrogen or halogen; ”Ruler 17 is Ci-C4 pit or alkyl; A, Ai, A2, A3 and A4 〇 or s respectively; L is hydroxy, halogen, crC3 alkoxy or (: factory ^ alkylthio; M is halogen or (^-(: 3 alkyl; Z is Ν or CH; Z1 is NR9 or 0; Is OR7 or NR9R10; r is an integer of 0, 1, or 2; and q is an integer of 2, 3, or 4. The present invention also relates to a composition containing these compounds and a method of using these compounds and compositions. It has been found that the compounds of the present invention and compositions containing them can be used to control unwanted plants. The compounds of the present invention are particularly useful for selective control of unwanted plants present in crops Plants. Detailed description of the invention Neodymium M The present invention provides a method for controlling unwanted plants, including the application of weeding to the leaves of the plant or to the soil or water containing its seeds or other propagules ------ 10- This paper method Standard_ quasi (CNS) Α4 specification (21〇Χ 297ϋ7 --------- buckle 4 ------ IT ------ ^ (please read the precautions on the back before filling in this Page) V. Description of the invention (8 j. The effective amount of bu (3-heterocyclic phenyl) thirteen of the formula I) well-2,4,6_oxy or thiotrione compound. The present invention 1- ( 3-heterocyclic phenyl) -zhansangeng-2,4,6-oxyl or thiotrione compounds have the structural formula I:

Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy ^ where X ’Y, R’ Rl ’A, A !, and A21q are as defined above. The preferred compound of formula I of the present invention is where X is hydrogen or Nansu; γ is hydrogen or Nansu, nitro or cyano. R is hydrogen, Ci-C ^ alkyl, CrC4 alkoxymethyl, (Ci_c4 Regular oxygen) carbonylmethyl, c3-c6 alkenyl or c3-c6 alkynyl; Κ · 1 is hydrogen 'C3-C6 alkenyl' C3-C6 alkynyl or optionally substituted by a (^ (⑺ heart substituted C1 -C 6 burned base; R3 is 0H or 0R8; Ruler 3 is C 1-C6 base or base metal, press or _-organic ▲ cation; Q is selected from

Q1 Q2 qii _-11-The standard of this paper is the general Chinese National Standard (CNS) A4 format (210X297 mm) A7 B7 Printed copy of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs V. Invention description (9 R11 and Rl2 and their attachment The connected atoms are combined to form a salty ring, which rises to c2-c5 extended alkyl group or RiiRu with structural formula where S (0) ri is optionally substituted with one to three methyl groups or one or more subs · CR19-CR20 = CR21-, where Ris, Ri9, ^ and ^ are each hydrogen, pixel or methyl; A, eight and A2 are ◦; A3 and eight 4 are 〇 or s; Z is N Or CH; and, r is an integer of 0, 1 or 2. The herbicide of formula I of the present invention is more preferably wherein X and Y are each hydrogen, F or C1; R is hydrogen 'CrC4 alkyl, crC4 oxymethane Group, tiger oxygen) methyl, allyl or propargyl; 1 ^ is allyl, propargyl or optionally substituted with a c (〇) r3 alkyl; R3 is 0H or 0R8; R3 is Base; Q is selected from

s (〇) r Η Ο Ο R11 and Rl2 combine with the atoms to which they are attached to form a ring, of which RiiRu is an extended butyl group substituted with one to three methyl groups; -12- Winter Paper Scale_China Hjia Materials (CNS> A4 & grid (2lQx297 public)) A7 B7 5. Description of the invention (10 ·) 1, .A, eight, and eight 2 are 0; and, r is an integer of 0 or 1. The present invention is particularly useful The best compound of formula I for undesirable plants is where X is F or C1; Y is C1; R is Ci-C4 alkyl, allyl or propargyl; CH ^ CC ^ Rg;, R 8 For C 1 _ C 4 burning> Base: Q is (please read the notes on the back before filling this page)-{--装

,-= »A, eight! And eight 2 is Ο; and r is an integer of 0 or 1. The 1- (3-heterocyclic phenyl) -yes-Sanken-2,4,6-oxotris compound which is a particularly effective herbicide in the present invention contains: 3- {2- 气 -4-fluoro-5 -[5,6,8,8a-tetrahydro-1,3-dioxo-1H-imidazo [5,1-c] [l, 4] pyrimogen-2 (3H) -yl] phenyl} tetra Hydrogen-5-methyl-2,4,6-trioxy-chromo-sangen-1 (2H) -isopropyl acetate; 3- {2-gas-4-fluoro-5-[(tetraargon- 3-oxy-111,311- [1,3,4] (&gt; sedizazolidine [3,4- &amp;] tajin-1-ylidene) amino] phenyl} tetrahydro-5- Methyl-2,4,6-trioxy-chromo-trio-1 (2H) -isopropyl acetate; -13- This paper scale is applicable to China National Standard (CNS) Α4 specification (210Χ 297 mm) , Seeking the printing of 3 ύ 4 〇 8 A7 B7 by the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (11 J [2-Gas 4Gas_5- (Tetrahydroten 37_Trioxy also taste spit [5, ^] ^, He &quot; well_2 (3H) _yl) phenyl] tetrahydro-5-methyl-2,4,6-trioxytriphine 1 (2H) -isopropyl acetate: — 3_ [2_ 气 _4_ 气 _5_ (3_fluorophthalimide) phenyl] tetrahydrolmethyl-2,4,6_trioxyftriple · 1 (2H) _isopropyl acetate Ester; &gt; [2-Gas-5- (1-cyclohexyl ^ dicarboxyimidyl) glacial fluorophenyl] tetrahydromethyl-2,4,6-diox Sanken-1 (2H) -tert-butyl acetate; 3- [2-Gas-5- (l-cyclohexyldicarbodiimide) _4_fluorophenyl] tetrahydro_5_ methyl_2 , 4,6_dioxy, tri-1 (2Η) -isopropyl acetate; and 3- [2-gas-5- (1-cyclohexyldicarboxyimidimide) _4_ 气 phenyl ] Tetrahydro-methyl-2,4,6-trioxytrigen-1 (2Η) · Methyl acetate. Examples of the aforementioned functional elements are fluorine, gas, bromine and iodine. Used in the specification and patent application tcrC4 haloalkyl group, Crc3 haloalkyl group and Ci_c4 haloalkoxy group represent Ci_C4 alkyl group, CrC3 alkyl group or Mochang 4 alkoxy group substituted by one or more halogen atoms respectively. The above formula It contains alkali metal : Sodium, potassium, and lithium. The alkaline earth metals of formula I include magnesium and calcium. Furthermore, organic ammonium is defined as a positively charged nitrogen atom connected to one to four aliphatic groups each containing one to 7 T carbon atoms. The invention compounds are particularly useful for the selective control of unwanted plant species present in the Agricultural Consumers ’Cooperatives of the Ministry of Economy, Trade and Industry, and the preparation of compounds of formula I in which Q is Q1 can be prepared by standard conditions such as catalytic hydrogenation Reaction or chemical reduction method makes the formula of 3_ (3_nitrate Phenyl) _Zhan Sangeng_2,4,6-Oxygen or sulfur trisporium is reduced to form an amine of formula m, and an anhydride of formula Π and formula ... is preferably reacted at elevated temperature in the presence of an acid such as acetic acid The compound of formula I in which &amp; is hydrogen is formed, and the alkylating agent and base of formula V are used to make the &amp; in argon -14- surface paper scale applicable to the Chinese National Standard (CNS) A4 specification (210X 297 C. ΑΊ Β7 V. Description of the invention (12. The compound of formula I is alkylated to form a compound of formula I in which Ri is not hydrogen>. The reaction is shown in Flow Diagram I.

Flowchart I

R

° 2N \ ^ V &quot; N ^ NH A, X Y 丄 (II) [Η]

R --------- installed ------ ordered ------ quan C ί (please read the notes on the back before filling in this page) Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs &amp;

-15- This paper scale is applicable to China National Standard Rate (CNS) Α4 specification (210X 297mm) B7 5. Description of the invention (13.) ‘------ Flowchart I (continued)

Ring I)

P R

The Ministry of Economic Affairs, Central Bureau of Precincts and Staff Consumer Cooperatives prints, or, where Q is Q1 and is not to say the preparation of compounds of formula I can use the alkylating agent of formula V and the base to make 3_ (3_nitrophenyl) of formula y three, well-2,4,6-oxyl or thiotrione alkylation to form 3- (3-nitrophenyl) -t three of formula VI &quot; well_2,4,6_oxyl or sulfur Triketone, under standard conditions, the compound of formula VI is reduced to form an amine of formula νπ, and the amine of formula VII and the anhydride of formula IV are preferably reacted at elevated temperature in the presence of an acid such as acetic acid. The reaction scheme is shown in the flowchart π. 16- This paper scale is applicable to China National Standard (CNS) Α4 specification (210 X 297 mm) V. Description of invention (14 N 2ο A7 B7

Flowchart II 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 of Jing Jing before filling this page)

RIN VHU A -N

Y 1

_

NH

X alkali N fNο.

X 1 R

V

It

C

Or r B,-&amp;

X V: R— Nta2 ^ TN γn yi

R Η This paper uses Chinese National Standard (CNS) Α4 specifications (210 X 297 mm) SU4158 A7 B7 5. Description of the invention (15.) ·

The preparation of the compound of formula I, in which Q is Q2 and Z is CH, is prepared by an employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs by reacting an amine of formula VII with phosgene or thiophosgene in the presence of an inert solvent to form an isocyanate of formula VIII or Thioisogas acid ester, reacting isocyanate of formula VIII or thioisocyanate with amine ester of formula IX in the presence of triethylamine to form an intermediate compound, and using an acid or base in the presence of an inert organic solvent such as ethanol The compound is soiled. The reaction is shown in Scheme III. -18-This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X297mm) V. Description of the invention (16 ·: Μ Β7 Flow chart III s

R H2N'V ^^ N,

T R, A2 X Y 2 (VII) A3C people

R A &lt; ^ N &gt; ^ A3 A, CN, / N, / N, Y ~

X v Y A2 (VIII) K. --------- approved clothing ------ IT ------ e (please read the precautions on the back before filling in this page) R11, R22, R12 (IX)-(R22 = Alkyl) -19- The standard of the paper is applicable to the Chinese National Standard Falcon (CNS) A4 specification (210X 297 mm) A7 B7 Five , Invention Description (17 ·) · Flowchart III (Continued)

R I R

Alkali or acid i C2H5OH

R

(Please read the precautions on the back before filling this page).

, Printed by 1T Employee Consumer Cooperative of China National Standards Bureau, Ministry of Economic Affairs

The preparation of the compound of formula I wherein Q is Q2 and Z is nitrogen allows the isocyanate or thioisocyanate of formula VIII to react with the substituted hydrazine of formula X to form an intermediate compound, and the intermediate compound is cyclized with a base. The reaction scheme is shown in the flow chart IV -20- This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) A7 B7 V. Invention description (18 _ /.

Flowchart IV

(VIII)

Wear (please read the precautions on the back before filling in this page) Outfit. Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (R22 == alkyl) Order

τ R— N v = a2

1 1 A R

R U \ A. N- p ——N R12

A 4

X base

R

丫 Y ynYn, r A.

Y -21-This paper scale applies the Chinese National Standard (CNS) A4 specification (2 丨 OX29? Mm) A7 B7

V. Description of the invention (19 I where Q is Q3 The preparation of the compound of formula I may be the reaction of amine of formula III with sodium nitrite, sodium azide, acetic acid, hydrogen acid and sodium acetate or with sodium nitrite, hydrazine hydrate and acetic acid The azide of formula XI is formed, and the azide of formula XI is reacted with the isocyanate of formula X to form the desired compound of formula I where R! Is hydrogen 'and optionally an alkylating agent and base of formula V Alkylation of the compound of formula I which is hydrogen. The reaction is shown in Scheme V.

Flowchart V (Please read the precautions on the back before filling out this page)

R

(III)

N sets the Central Bureau of Standards of the Ministry of Economic Affairs: Printed by the Industrial and Consumer Cooperative

RIN Ku A N

Y

X V

T

NH

X

X

Rl (x

o c N -22- This paper scale is applicable to the Chinese National Falcon (CNS &gt; A4 specification (210X 297mm> 3u4io8 A7 B7

V. Description of the invention (20 T flow chart V (continued),

Rii order Ν

Outfit-ί (please read the notes on the back before filling this page)

The preparation of a compound of formula I in which Q is Q4 is produced by an employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. The compound of formula I in which Q is Qii ... and ~ oxygen is reacted with sodium hydride to form a compound in which L is oh Compounds in which L is OH react with alkali and suitable alkylating agent to form compounds with 1 ^ CrC3 alkoxy group or compounds in which l is 0H and halogenating agent such as tri-vaporized soil, sulfite gas, tri-fill Chemical discrimination, triphenyl pentoxide, triphenyl sulfonate or triphenylphosphine-broken in an inert solvent-such as gaseous reaction, to form a compound in which L is halogen, and then make the compound in which L is halogen and (^- (: 3 alkyl-sulfur bond reaction to form a compound in which L is Cj-C] sparse group. The above reaction scheme is shown in Flow Diagram VI. 23- This paper scale is applicable to China National Standards (CNS) A4 specification (210X 297 Mm) A7 B7 5. Description of the invention (21 ·) '

Flowchart VI N

R

D

NaBH, Τ5

(Please read the precautions on the back first and then fill out this page). Installed, -α Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs -24 This paper is applicable to China National Standard (CNS) A4 (210X 297mm) B7 V. Description of the invention (22 · Halides

R

Flow Chart VI (Performance) Test. (C ^ -C ^ Hyunki) &amp; (X = Cl, Br or I) alkyl sulfide

R

Ό

R

X Υ The preparation of the compound of formula I in which Q is Q5 is printed by the Beigong Consumer Investment Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. The standard method of amine of formula VII can be azotized to form an intermediate compound, which is reduced with sodium sulfite to form hydrazine of formula XIV . This hydrazine is then reacted with the imine ether of the formula XV to form the amide of the formula XIV. -25- This paper is once again a universal towel. The national standard (> A4 is now grid center 29? Male thin) Μ Β7

V. Description of the invention (23. amidrazone) and, in the presence of triethylamine and the presence of triethylamine, react the amide knee with phosgene or a suitable phosgene equivalent to form the desired compound. The reaction is shown in the flow Figure VII. Flowchart VII

R

R, 1) Azo 2) Na2S〇3 (Please read the precautions on the back before filling in this K). Packing. -11 Printed by Employee Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs

R I

-26- The general Chinese national standard (CNS) A4 format for this paper (210X297mm) A7 B7 5. Description of the invention (24 ’) 'Flowchart VII (continued)

(XVI) (c2h5) 3n COCl2 ▼

(Please read the precautions on the back before filling out this page-the binding of the Ministry of Economic Affairs Central Standards Bureau Staff Consumer Cooperative printed the compound of formula I in which Q is Q6. It is condensed in the presence of a base to form an intermediate compound, and the intermediate compound is reacted with phosgene or a phosgene equivalent. The reaction is shown in the flow chart VIII. -27- This paper scale uses the Chinese National Standard Falcon (CNS) A4 (now 210X297mm) 5. Description of invention (25 A7 B7

Flowchart VIII

R

R-, inspection

R12 2C = CHN HN

R11 X Please read the notes on the back to fill in the pretense page

R ▼

, Vh R12 (XVII) V, v C0C1 2 Printed at the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

X Υ -28- The standard of this paper is applicable to the Chinese National Standard (CNS) Α4 specification (210Χ 297 mm) 304158 Α7 Β7 V. Description of the invention (26 · j, where Q is Q7 and the preparation of the compound of formula I can make formula VIII The isogas ester reacts with the substituted alkyne of formula XVIII in the presence of the test and optionally at elevated temperature. The reaction is shown in Reaction Scheme IX.

Flowchart IX

R

Alkali p R13c = ccRllRl2 (XVIII) {(Please read the precautions on the back before filling this page), τ

The preparation of the compound of formula I in which Q is Q8 and M is basic is prepared by the employee consumer cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Reacts in the presence of a base such as triethylamine or sodium acetate in an inert solvent such as ethanol or toluene to form 2,3-dihydroxypyrazol-3-one of formula XX, and a denaturant such as phospha or phospha Bromine functionalizes the compound of formula XX. The reaction is shown in flow chart χ. -29- This paper scale is applicable to China National Standard (CNS) Α4 specification (210Χ297mm) A7 B7 5. Description of invention (27 〇

Flowchart X

R

(XIV) 〇 〇0 (\-&lt;: 4 alkyl)

Τ 'R11 (XIX) R

(Please read the precautions on the back before filling in this page)-Binding-Travel Printed by the Employee Consumer Cooperative of the Central Prototype Bureau of the Ministry of Economic Affairs

X ν Υ -30-This paper scale is applicable to the Chinese National Standard (CNS) Α4 specification (210X 297 mm) A7 B7 V. Description of the invention (28 y where Q is Q8 and the percentage is CrC3 alkyl]] The hydrazine of formula XIV and the 1,3-dione of formula XXI are optionally reacted in an inert solvent in the presence of a base. The reaction is shown in Scheme XI.

Flowchart XI

R Please first «Read the notes on the back" item

(XIV) (CfC ^ Tiger) Γ (XXI) P 0

Binding R11 alkyl)?

The preparation of the compound of formula Ί in which Q is Q9 can be printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. • The amino acid reacts in the presence of triethylamine. The reaction scheme is shown in Flow Diagram XII. -31-This paper music standard uses the Chinese National Standard (CNS) A4 specification (210X 297mm) A7 B7 5. Description of the invention (29 ·) '

Flowchart XII

R I

R, 0 R 11

(Please read the precautions on the back before filling out this page). Binding · Ordered by the Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperatives where Q is Q10 of the compound of formula I-preparation of hydrazine of formula XIV and formula XXIII For example, the reaction in the presence of triethylamine or oral bite forms aryl hydrazide of formula XXIV, and the aryl hydrazine and tricarboxylic acid methyl ester of phosgene, phosgene or suitable phosgene are equivalent in triethyl Reaction in the presence of amines. The reaction scheme is shown in Flow Diagram XIII. 32- This paper scale is in accordance with the Chinese National Standard Falcon (CNS) A4 specification (2! Ο X 297 g) Μ Β7 5. Description of the invention (3〇 彳 Flow chart XIII Ν

R I Η2ΝΝΗ \ ^ Ν / Ν- -Ν 'Ύ • Ri (XIV)

οII base R12CX1 (XXIII) (X1 = cl, Br ^ I)

T

R (Please read the precautions on the back before filling in this page) • Install ·

oII R12CNHNH

XN YA 'Y A2 Order ▼ Printed by the Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperative (XXIV) COCl2 or C1C02CC13 33- This paper scale is applicable to the Chinese National Standard (CNS) A4 specifications (210X297 mm) (31 '). Flowchart XIII (Results \

Where Q is Qll, A3 is sulfur, a4 is oxygen and Z is CH, the preparation of the compound of formula I can react the thioisocyanate of formula VIII with the amine of formula χχν to form thiourea of formula XXVI 'and make the thiourea and formula The carbonyl halide of XX VII is reacted in the presence of a base. The reaction is shown in Scheme XIV.

Flow circle XIV --- I---I 1 (--1- I In 1 I I--* ·, 1 I-(Please read the notes on the back first and then fill in {巧 太-百 〇

SCN

X

YA R1 A_ Y 2 玎 (VIII) Printed by the Cooperative Society of the Ministry of Economic Affairs, Central Standards Bureau ▼ R11NH2cxxvj -34- This paper scale applies the Chinese National Standard (CNS) Α4 specification (21 ο X 297; t) ^ 04138 5 3. Description of the invention (32 \ Ί Β7 Flow chart XIV (Continued) RI 11

0 II X1C (j: HX1 test

V (Please read the precautions on the back before filling out this page).

* 1T

R

o R12 (XXVII) (X, = Cl, Br or I) R 12 s

R, Printed by a Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs where Q is Qll, A3 is sulfur, A4 is oxygen and Z is nitrogen. The reaction forms an intermediate compound of formula XXIX and reacts the intermediate compound with phosgene or a suitable phosgene equivalent in the presence of a base such as triethylamine. The reaction sequence is shown in the flow chart XV. 35- This paper scale is applicable to the Chinese National Standard Falcon (〔: ^) 6 4 specifications (; !! 0: &lt; 297 mm) V. Description of the invention (33 A7 B7 Flow Chart XV &gt;

R

X r12nhnhr1; l (XXVIII)

(XXIX) Alkali C0C1 2 (please read the precautions on the back first and fill in this page).

, 1T Λ. Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

R

X R, R ,,

Rl2 \ ^ V. People> Where Q is Qll, A3 and A4 are oxygen and Z is CH Preparation of the compound of formula I -36 This paper ru scale applies the Chinese National Standard (CNS) A4 specification (210: &lt; 297 Gongcheng) A7 __B7_ V. Description of the invention (34 j, the isocyanate of formula VIII can be reacted with the hydride of formula XX V to form a urea of formula XXX, and the veins can be dehydrated to form a few imides of formula XXI, and the imidates of formula XXVII can be combined Carbonyl halide reacts to form haloamidine of formula XXXII, hydrolyze the haloamidine with aqueous acid to form urea urea, heat the urea in situ to form urea urea of formula XXXIII, make 0- urea and base such as triethylamine The reaction is shown in Flow Diagram XVI.

Flowchart XVI (please read the notes on the back before filling in this page).

RUNH2 u (XXV) Ordered by the Central Bureau of Economic Development of the Ministry of Economic Affairs-Industrial and Consumer Cooperatives

-37- This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X 297mm) V. Description of the invention (35 ’:

R11N = C = N

X A7 B7 Flowchart XVI (Continued, R IΝγΝχ (XXXI)

οII X1Cj: HX] R, 12 (XXVII) (x2 = Cl, Br or I)

R

R 12

O xa λ ^ γ} ί ^ γΑ1

N—C = N

X, R 11

X

Y 丫 XA, I i---n-n! — 士 K-In —i-I; 1 丁 ―——-----------. 良 K ， V6- ^ (Please read the back side first Please pay attention to this page and then fill out this page). I- ___K ____ (XXXII) Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs ▼ 1) Hn0H 2) △ 38 210X 297 male thin) 5. Description of the invention (36) A7 B7

R 12 Flow Chart XVI (Continued)

, 11

0 ^ Y ^ 〇-C = N

(XXXIII) alkali

R

(Please read the precautions on the back of the ear and fill out this page). Ding -5 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

The preparation of the compound of formula I wherein Q is Q12 allows the reaction of the amine of formula VII with the anhydride of formula IV to form the acid-amide of formula XXXIV, and the acid-amide is dehydrated with a dehydrating agent such as 1,3-dicyclohexylcarbonyldiamide Imine dehydration. The reaction scheme is shown in the flow chart XVII 39- This paper scale is applicable to the Chinese National Standard (CNS) Λ4 specification (210 X 2?> 7 mm) V. Description of the invention (37 A7 B7

Flow Chart XVII H2N ^ vi ^ V ^ N, 『τ R, A2 x y 2 (VII)

R 11 R

12 (IV) A, (Please read the precautions on the back before filling out this page. Install. T

R 、-»

R 11

A3 II CNH R12A ⑽x

NYN, y A2 (XXXIV) Central Bureau of Standards of the Ministry of Economic Affairs *: Printed by industrial and consumer cooperatives -H2〇 T &gt;

N \ / N, Y R] Y A2

R I 40- This paper scale is applicable to Chinese National Standard (CNS) A4 specification (2 丨 0X 297mm) V. Description of invention (S8 ·) 1 ·

The preparation of the compound of formula I wherein Q is Q13 allows the reaction of thiourea of formula XXVI with methyl iodide to form isothiourea of formula XXXV, and the reaction of isothiourea with gas M of formula XXXVI. The reaction scheme is shown in Flow Diagram XVIII. Flowchart XVIII

SII R11NHCNH

(XXVI) ch3i (Please read the precautions on the back before filling out this page.

, 1T

SCH

3 R1; LNHC = N

NOH (XXXVI) 12 -41-This paper standard is applicable to China's Jiaojia standard (CNS) A4 specification (210X 297 mm) A7 B7 V. Invention description (39 · ί Flow Chart XVIII Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (Yi)

R

The preparation of the compound of formula I where Q is Q14 allows the amine of formula VII to react with the gas formate of formula XXXVII to form the amine ester of formula χχχνπι, and the Under the presence of reaction. The reaction scheme is shown in Flow Diagram XIX.

Flowchart XIX

R

〇

ClCCMCfC ^ Alkyl) (XXXVII) 42- The standard of this paper is applicable to the Chinese National Standard (CNS) A4 specification (210 '297mm) ^ Binding ^ f C (Please read the precautions on the back before filling this page) A7 B7 V. Description of the invention (40'y flow chart XIX (continued))

R Η γf (C1_C4 burned base) 〇 Α: magnetism (XXXVIII)

f〇- ^ ° A &lt; 55 | / Nv «^ A] (Please read the precautions on the back before filling this page) • Discarded · JS6

R

11 R 、 12

X χτΝγΝχ A.

Y The Ministry of Economic Affairs Central Standard Falcon Bureau Employee Consumer Cooperative printed the preparation of the compound of formula I in which Q is Q15. The amine of formula VII can be reacted with ethyl formate to form the carbamate of formula XL, and the carbamate Reacts with hydroxy ester of formula XLI. Elevated temperature and removed ethanol. The reaction is shown in Flow Diagram XX. -43- The scale of this paper is applicable to China National Standard Falcon (CNS) A4 Saoge (21〇'X297 芨) A7 B7 5. Description of the invention (41 ·) '·

Flow chart XX?

(VII) C1C〇2C2H5

(Please read the precautions on the back first and fill out this page).

R

Printed by the Consumer Labor Cooperative of the Central Bureau of Economic Affairs of the Ministry of Economic Affairs or where Q is Q15. The preparation of the compound of formula I can make the difference of formula VIII -44-This paper scale is applicable to the Chinese National Standard Falcon (CNS) A4 specification (210X297 public interest ) A7 B7

t &gt; u415S V. Description of the invention (42 ′) The reaction of the cyanate ester with the hydroxy ester of formula XLII to form the intermediate compound of formula XLIII and the reaction of the intermediate compound with a base such as sodium acetate in an inert solvent such as toluene is shown in the flow chart XXI.

Flow chart XXI

R

H5C2〇2C --------— seed coat ------- ST ------. ^ Ί (Please read the precautions on the back before filling this page)

(XLIII) 12

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

R o x γ

R -45- This paper scale applies to China National Standard (CNS) A4 specification (210X297 mm) 304158 Δ7 Α7 Β7 5. Description of the invention (43'y. Where Q is the preparation of the compound of formula I of Q16 + the formula of νπl Isocyanate reacts with the α-amino-α, /?-Unsaturated ester of formula XLIV to form the vein of formula v, and make the step and test as sodium acetate in an inert solvent such as Ace + T at elevated temperature The reaction is shown in Flow Diagram XXII.

Flow chart XXII

R (Please read the precautions on the back before filling out this page) Install ‘

R

NHR 11 14 C〇2CH3,-°

R R 14 Printed by the Employee Consumer Cooperative of the Central Standardization Bureau of the Ministry of Economic Affairs

\ C (XLIV) R R

(XLV)-Insurance-Brigade

R 13 -46- This paper scale is applicable to China National Standard Leather (CNS> Α4 specification (2 丨 ΟΧ 297mm) Λ 7 Β7 V. Description of the invention (44 ·) Flowchart XXII (continued)

Alternatively, the preparation of the compound of formula I in which Q is Q16 allows the isocyanate of formula VIII to react with the amino acid of formula XL VI to form a urea of formula XL Vir, and the reaction of urea with an acidic aqueous solution to form the internal compound of formula XLVIII Urea, and reacting urea with acetal of formula XLIX. The reaction scheme is shown in Flow Diagram XXIII.

Flowchart XXIII (please read the precautions on the back to fill in this page). Install.-»

(VIII) Printed by the Consumer Labor Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

V R1: lNHCH2C〇2H (XLVI) -47 The standard of this paper is applicable to China National Standard (CNS) A4 specification (210X 297mm) A7 B7 5. Description of invention (45 ·)

(XLVII) H3 ° (Read the precautions on the back and then fill in this page). Install t 0

R 11

R

(XLVIII) Printed by the Central Bureau of Standards of the Ministry of Economic Affairs, printed by the Consumer Cooperative Society r13r14c (〇ch3) (XLIX) '

R

48 The size of this paper is in accordance with Chinese National Standard (CNS) A · 4 specifications (210X297mm) A7 B7

V. Description of the invention (46 〇 '. Where Q is Q17 for the preparation of the compound of formula I. The isocyanate of formula Vni is reacted with the ester of enoic acid of formula L in the presence of triethylamine. The reaction is shown in Flow chart XXIV. Flow chart XXTV R

OCN

AiVNYA]

(VIII)

R (Please read the precautions on the back before filling in this I) • Install. Ik ▼ 13

R 14 HO ^ VC〇2CH3 (L)

, 1T

R O

A ^ N YAA] The preparation of the compound of formula I in which Q is Q18 is printed by the Consumer Labor Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. Next reaction. The reaction is shown in flow chart XXV. • 49 This paper wave scale general Chinese national standard (CNS) A4 specification (2Ι〇χ male S) V. Description of invention (47.

Flow chart XXV H ^ N

Sense 0 '(CR14R15) q acid t

(LI)

R

The preparation of the compound of formula I where Q is Q19 can be obtained by the preparation of the compound of formula I where Q is Ql 'A3 and' is oxygen and heart is hydrogen and the formula Lii The Grignard reagent reacts at elevated temperature in a solvent such as acetone or tetrahydrofuran to form an intermediate compound of formula B. This intermediate compound reacts with potassium bisulfate at elevated temperature to form the desired compound of formula I in which Ri is hydrogen, and The desired compound of formula J in which Ri is hydrogen is alkylated with the caustic agent of formula v in the presence of alkali. The reaction step is shown in the flow chart XXVI. This paper scale is applicable to China National Twinning (CNS) Λ4 gauge pile (- 50-210X297 Gongqing) V. Description of the invention (48 A7 B7

Flowchart XXVI

^ MgBr; R13 ^ 14

R

(LIU) (Please read the precautions on the back before filling this page)-Install.

, 1T Printed by Beigong Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs KHSO Δ 4 51-The long scale of this paper is applicable to the Chinese National Standard (CNS) A4 (2l〇X 297mm)

, Description of the invention (Ming ·) "· Flowchart XXVI (4)

V R

R1X1 (V), r (Xi = Cl, Br or I)

R

(Please read the precautions on the back before filling in this page). Packing. The preparation of the compound of formula i in which Q is Q20 is printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. Acetic acid is reacted with a catalytic amount of acetic acid in acetic acid and at elevated temperature or in dimethylbenzene at elevated temperature with a catalytic amount of p-toluenesulfonic acid. The response is shown in flowchart XXVII. --52- This paper wave scale is applicable to China National Standard (CNS) Λ4 specification (210X 297mm) V. Description of invention (5〇 ') A7 B7

Flowchart XXVII

R A &lt; 5 ^ N &gt; V ^ &gt;A; 1

0 (LIV)

R

X Υ

Please I read it first I read I read the back I5 things I Item I :!

Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Alternatively, the preparation of the compound of formula I in which Q is Q20 allows the amine of formula VII and the diacid of formula LV to react in xylene at reflux. The reaction is shown in Flow Diagram XXVIII. -53- This paper scale is applicable to China National Standard (CNS) Α4 specification (210Χ 297mm) V. Description of invention (51 A7 B7

Flow chart XXVIII A · R. Α Χ Υ (VII)

R13 \ CO.H &gt; = &lt; 2 R / K14 r \ CH2C〇2H (LV) R Please read the back winter winter animal items • s.

IT

14 Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. : xx: r 'Where Q is Q21, the preparation of the compound of formula I allows the amine of formula VII to react with malondiuretane and sodium nitrite in acetic acid with a catalytic amount of concentrated hydrochloric acid to form a hydrazone of formula LVI, The hydrazone is cyclized with a base to form triplodione of formula LVII, and thioglycolic acid is used to decarboxylate tricrosandione at elevated temperature and optionally with an alkane and a base such as sodium hydride where Q is Q21 and Rn is Hydrogenation of compounds of formula I is alkylated. The reaction is shown in Flow Diagram XXIX. -54 The scale of this paper is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 gong) 5. Description of the invention (52 ·

R I A7 B7

Flow chart XXIX η2ν u,, \ + NaN〇2 + H2C (CONHC〇2C2H5) 2A.

X 2 Y (VII) ch3c〇2h hci / h2〇

t R

(LVI) Inspection (Poetry first read the precautions on the back and then fill out this page)-Packed. Ordered by the Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperative Printed -55- This paper scale is applicable to the Chinese National Standard (CNS) Λ4 specification (210X 297 5) Description of invention (53 H〇2C-

X A7 B7 Flow Chart XXIX (4)

R 义 丫 0 Α &lt; γΝγΑ] χΛΛγ α2 (LVII)

HSCH2C〇2H Ν

eyelid

? U Δ

R ΝΥΝ 'R11X1 = Cl, Br or I)

R (Please read the precautions on the back before filling out this page)..-Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

〇, / N YA0, N YA0

X

N

nyn, r] A * y 2 Or, the preparation of the compound of formula I in which Q is Q21 and Ru is hydrogen can make the formula -56 of the paper scale applicable to the Chinese National Standard Semi (CNS) A4 current format (210X 297 Gong |) A7 B7

V. Description of the invention (54. The hydrazine of XIV reacts with propylene in a sulfuric acid solution to form the knee of formula L VIII. 'The hydrazone reacts with potassium cyanate in an acetic acid solution to form a triazolidine of formula LIX. Sanjun bite reacts with acetic acid and phobic acid. The reaction is shown in flow chart XXX. Flow chart XXX

R I h2nnh (XIV) Acetone, H2s〇4 (Please read the precautions on the back before filling this page) • Install ·,-° ♦

R h3c> H3Ci Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy Α · Ϊ ^ Ν '· ^ Α]

Only, KOCN CH, C0, H / H, 0 -57- The paper size is applicable to the Chinese National Standard (〇 ”5) 44 specifications (210 ′ × 297 mm) A7 B7 V. Description of the invention (55 ·).

R

Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

Where Q is 〇22 and R! Is not hydrogen, the preparation of the compound of formula I allows the isocyanate of formula νπl and the amine of formula LX to react in the presence of a base such as sodium hydride to form an intermediate compound of formula LXI, and optionally acid The intermediate compound is cyclized in the presence of a base, and the compound of formula I in which ^ is Q22 and R16 is hydrogen is alkylated with CrC3 pit halogen and sodium hydroxide as appropriate. The reaction is shown in the flow chart XXXI-58- The standard of this paper is applicable to the Chinese national standard falcon (CMS) A4 specification (210 X 297 male thin) V. Description of the invention (56 A7 B7

Flowchart XXXI

R Αχ / Ν ^ Α】 Ya 1 -R]

r. N (VIII)

R11V (Please read the precautions on the back before filling in this page)

h2n r) (LxV 12 R R 11

(LXI)

V set Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 59- The standard of this paper is applicable to the Chinese National Standard (CNS) Λ4 specification (210X 297mm) A7 B7 V. Invention description (57 Flowchart XXXI (4)

R

Alkali crc3 alkyl halide

XY Ministry of Economic Affairs, China National Bureau of Standards, Beigong Consumer Cooperatives, Indo-Chinese, where the compound of formula I with Q being Q23 can react the amine of formula LXII with the formula of LXIII ", that is, unsaturated vinegar to form the amine ester of formula LXIv and make the amine The ester reacts with an isocyanate of the formula νΠι followed by heating under acidic conditions. The reaction sequence is shown in the flow chart XXXII. ----------- Bai Yi ------ ir ------ rong ^ (Please read the precautions on the back before filling out this page) 60- This paper · Standards are applicable to the Chinese National Standard (CNS) Α4 specifications (210Χ 297 Gongqing) 3ύ41〇8 5. Description of the invention (58 ·) · A7 B7 R15NH2 (LXII) Flow chart XXXII + R12CH = CHC〇2CH3, (LXIII) ί R15NH (pHCH2C〇2CH3

1) OCN ^ r ^ / N

(Please read the precautions on the back before filling in this page.

R 15 R

Printed by the Central Bureau of Standards of the Ministry of Economic Affairs-Industry and Consumer Cooperatives ^ where Q is Q24 The preparation of the compound of formula I allows the reaction of hydrazine of formula XIV with propionate of LXV, followed by cyclization under acidic conditions to form the formula of LXVI Dihydropyrrolidone and dihydropyrrolidone with gas quinone or 1,3-digas-5,6-dicyanobenzene (DDQ) in an inert solvent such as dihydropyridine or toluene at elevated temperature The ketone is dehydrogenated and the reaction is shown in Flow Diagram XXXIII. 61-This paper scale is applicable to the Chinese National Standard (CNS) Μ specification (210X297mm) V. Description of the invention (59 ’) A 7 B7

Flowchart XXXIII

R Η2ΝΝΗ \ ^ Γ ^ Ν 丫 N, r) A2 (XIV) r17 〇112 li 1) W / CH YA (LXV) R + 2) acid — HCH 11

P

△ (Please read the precautions on the back before filling in this page. Packing. Ordering: 1 Employee consumption cooperation of the Central Standards Bureau of the Ministry of Economic Affairs. Du Yin-62 This paper is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 Mm) A7 B7 5. Description of the invention (60 ·) Flowchart XXXIII (continued) R ϋ

A, R, where Q is Q25, the preparation of the compound of formula I allows the isocyanate of formula VIII to react with the acetonide of formula LXVII at elevated temperature. The reaction is shown in Flow Diagram XXXIV.

Flowchart XXXIV

• R (Please read the precautions on the back before filling in this page. Install ·,-»

R, Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Ο Δ

(LXVII) This paper scale is applicable to the Chinese National Standard Falcon (CNS> A4 specification (210X 297 mm) A7 _ B7 V. Invention description (61 · / · Flowchart XXXIV (½)

Where Q is Q26, the preparation of the compound of formula I allows 3- (substituted phenyl) -i-Sanken-2,4,6-oxyl or thiotrione of formula LXVIII and acetonitrile to be present in the vaporized aluminum Under the reaction, the ketone of formula LXIX is formed. The ketone is reacted with the ester of formula LXX to form the diketone of formula LXXI, and the diketone is reacted with the hydrazine of formula LXXII to form the formula I in which Q is (^ 26 and R10 is hydrogen Compounds, and optionally halogenate compounds of formula I where q is Q26 and R16 is argon. The reaction is shown in the flowchart χχχν. (Please read the precautions on the back and then fill out this page) Printed by the Central Bureau of Standards, Male Workers' Consumer Cooperative V. Description of Invention (62 ·: A7 B7

R

Flowchart XXXV .〇

II CH3CC1 / A1C13 R — (Please read the precautions on the back before filling this page).

Ys Alkali Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy R14C02 (C; TC4 alkyl) (LXX) ▼

h2nnhr13 (LXXIJ.) 65 This paper scale is applicable to China National Standard Falcon (CNS) Λ4 specifications (2! 0 X 297 mm) 304158 a7 B7 Five 'invention description (63') ', · Flowchart XXXV (-4)

R

(x2 = Nansu) (Quote to read the back of the &quot; Issues st. Fill out this page-Pretend,-= 5 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs where Q is Q27. Reacting a ketone of formula LXIX with a carbonate or thiocarbonate of formula LXXIII in the presence of a base to form an ester or thioacetate of formula LXXIV, reacting the ester or thioester with a hydrazine of formula LXXII to form an intermediate compound of formula LXXV, and The intermediate compound is alkylated with an alkylating agent of formula LXXVI in the presence of a base to form a compound of formula I in which Q is Q27 and R16 is hydrogen, and optionally a compound of formula I in which Q is hydrogen of Q27 and R16 is halogenated. The diagram is shown in the flow chart XXXVI. -66- The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) V. Description of the invention (64 A7 B7

Flowchart XXXVI

X ν Υ (LXIX) A. 絵: A,

II topography) 2 i (LXXIII) R (q-q alkyl) 0

(LXXIV) h2nnhr13 (LXXII)? (Please read the precautions on the back before filling in this page)-Pack. Order Printed by Employee Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs t

(LXXV). R17X1 base (LXXVI) (X, = Cl, Br or I) -67- This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (2 丨 OXM7mm) Α7 Β7 V. Description of invention (65 ' ί Flowchart XXXVI (Continued)

R

R, halide

(Please read the notes on the back side first and then fill in this page) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (X2 = halogen) where Q is Q28 The preparation of the compound of formula I can make the aniline of formula LXXVII and the formula of LXXVIII Isocyanate or thioisocyanate reacts to form urea or thiourea of formula LXXIX, urea or thiourea is cyclized with isocyanate or thioisocyanate of formula LXXX to form 3- (substituted phenyl) -color-three of formula LXXXI Geng-2,4,6-oxyl or thiotrione, 3- (3-substituted phenyl) three-growth-2,4,6-oxyl or thiotrione in sequence with alkali, sulfenyl gas It reacts with hydrazine of formula LXXII to form an intermediate compound of formula LXXXII, and reacts the intermediate compound with phosgene or a phosgene equivalent to form a compound of formula I where Q is Q28 and 1 ^ is hydrogen-68 Applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) A 7 B7 V. Description of invention (66), and according to the situation, where the alkylating agent of formula V is in the presence of alkali>, let Q be Q28 &amp; R1 is Hydrogenation of compounds of formula I is alkylated. The reaction is shown in Flow Diagram XXXVII.

Flowchart XXXVII (Please read the precautions on the back before filling this page)-Install.

RNCA (LXXVIII) 1

II

C1CNCA (LXXX) Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs -69- Applicable to the Chinese national standard for clothing paper standards (CMS> M specifications (210x297 public)) 5. Description of invention (67 ') A7 B7 Flow chart XXXVII (continued)

R

ΑγΝ 丫 』(C -C4 alkyl) 0 T X v Y (LXXXI) A. 1) base 2) S0C1 · 3) H2NNHR ~ 3 τ (LXXII)

R 13

(LXXXII) binding '^ (f (please read the precautions on the back before filling in this page) I ____ I_' ·-_ Printed C0C1.-70 by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. -70 This paper is applicable to the Chinese national standard (CN'S ) Λ4 specification (2 丨 0X29? Mm) 304158. V. Description of the invention (68 A7 B7 flow chart XXXVII (continued) 0 R '13

R1X1 (V) (Χα = Cl, Br or I)

♦ R

The preparation of the compound of formula I in which Q is Q29 can be printed by the Consumer Cooperative of Central Central Bureau of Economics of the Ministry of Economic Affairs. The preparation of the compound of formula I in which LXIX can react with the amidine of formula IXXXIII forms the compound of formula I in which Q is Q29 and Ri6 is argon, and The situation makes the compound of formula I wherein Q is Q29 and R16 is hydrogen. The reaction scheme is shown in flowchart XXXVIII. -71-This paper scale is applicable to Chinese national standards ((1 (^ 5) 44 specifications (210/297 gala) A7 B7 V. Description of invention (69》

Flow chart XXXVIII 0 h3c, R I A ^ / N'Y ^ A1YA R: (LXIX) NH Jk / R,

R ,,, N v14

H (please read the notes on the back first? R fill in this page) ___f _ outfit-(Lxxxm)

R

R 14

Order of the Halide Ministry of Economy Central Standard Falcon Bureau Employee Consumer Cooperative

R

R 14 Α ^^ Ννγ ^ Α]

-72- The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 304158 A7 B7 V. Description of invention (70%, where Q is Q3 0 and 1 is hydrogen. The amine of formula LXXXIV reacts with the isocyanate or thioisocyanate of formula LXXVIII to form the urea or thiourea of formula LXXXV, and the urea or thiourea is cyclized with the isocyanate or thioisocyanate of formula LXXX to form 3- (substituted Phenyl) -deficient-Sanken-2,4,6-oxyl or thiotrione, 3- (substituted phenyl) Biansanp well-2,4,6-oxyl or thiotrione in order Reduction with ammonium hydroxide and a gasifying agent to form a fat of formula LXXXVII, and reacting the fat with an alkyne of formula LXXXVIII to obtain a compound of formula I wherein Q is Q30, hydrogen and Z2Λ alkoxy, The compound is sequentially reacted with acid or base, sulfite gas and amine of formula LXXXIX according to the situation to obtain the compound of formula I in which Q is Q30, &amp; is hydrogen and Z2 is NR9R1 (). The reaction is shown in the flow chart XXXIX.

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

(LXXXIV) Ministry of Economic Affairs Central Standards Bureau employee consumption cooperation du printed RNCA (LXXVIII) -73- This paper standard uses the Chinese National Standard (CNS) A4 specifications (210X 297 mm) V. Invention description (7Γ: 3ϋ4 Vice- Flowchart XXXIX (continued)

0 Η Ηη- VN YN &quot; R

II 2 C1CNCA ★ (LXXX) ι

R

(Please read the precautions on the back and then fill in this page)-Pack. Order the printed bag of the Consumer Standard Cooperative of the Central Standard Falcon Bureau of the Ministry of Economic Affairs (LXXXVI) 1) νη4〇η 2) Chloride ▼ -74- This paper size applies to China National Standard (CNS) Α ·) Specification (210X 297mm) U8 A 7 B7 V. Description of the invention (72 '/, Flow chart XXXIX (continued)

(LXXXVII) RuCECCO ^ CfC ^ alkyl) (LXXXVIII)

(Please read the precautions on the back before filling out this page) Pack. Order Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

1 R

1 -75- The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 3 ^ 4158 A 7 B7 5. Description of the invention (73 ') · where Q is Q30 and R1 is not hydrogen formula I The preparation of the compound can make the compound of formula I in which q is Q3 0 and 1 ^ is hydrogen with the alkylating agent of formula V in the presence of a base. The reaction is shown in Flow Diagram XL.

Flow chart XL (please read the notes on the back before filling in this page).

Br or I)

▼ W — (V) (Xj = cj R

, Α 1 --- °

R

X

Y Where Q is Q31, the preparation of the compound of formula I allows the 3- (substituted phenyl) -Zhansanken-2,4,6-oxyl or thiotrione of formula LXVIII to be esterified with the ester of formula XC In the presence of the reaction, an intermediate compound of formula XCI is formed, and the intermediate compound is reacted with a substituted amine of formula XCII. The reaction scheme is shown in the flow chart XLI. -76- This paper applies to the national standard (CNS) A4 specification (210 X 297 g; f)

A Impression of the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy V. Description of the invention (74 A7 B7

Flowchart XLI

R x YA1

Y (LXVIII)

oII (&lt; 21-〇4alkyl) 〇〇: || 〇1 (XC) A1C1 3 (please read the precautions on the back before filling this page)-installed. o

R

(XCI) Η ΝΗ Order

R 2 Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

R

(XCID 12

R / W 2 1

-77- The paper scale is applicable to China National Standard Falcon (CNS) AA specification (210X297mm)

R Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs R 11 12

4138 A7 __._ B7 V. Description of the invention (75 ')' where Q is Q32 The preparation of the compound of formula I allows the isocyanate or thioisocyanate of formula VIII and the amine ester or thiothioester of formula XCIII in an inert solvent and It is better to react at elevated temperature. The reaction is shown in Flow Diagram XLII.

Flow chart XLII

R A2 (VIII) R12 A4 (XCIII)

R n \ ^ A3 Νγγν, A2 78 This paper music standard is applicable to the Chinese National Standard (CNS) Λ4 specifications (210 X 297 mm) (please read the precautions on the back and fill in this page)

Y A7. B7 V. Description of the invention (76 y ·-where R3 is NR9R10, the preparation of the compound of formula I can be prepared using standard procedures, such as hydrolysis of a suitable ester of formula XCIV in the presence of trifluoroacetic acid, so that the resulting acid It reacts with sulfite gas to obtain the compound gas of formula XCV, and reacts the compound gas of formula XCV with the amine of formula LXXXIX in the presence of a base according to the situation to obtain the desired product. The reaction is shown in Scheme XLIII.

Flow chart XLIII

Ύ 、 (C ^ C12 alkyl) C〇2C (CH3) 3

X (XCIV)

1) CF3C〇2H 2) SOCl. ---. HI I- -1--I----1-ii. N t-. I -i ^ i · il II-- II. I— 一 J. i—.. 1. ——. , (-^ (Please read the precautions on the back before filling in this page).: _ / _____ Printed by the Central Standard Falcon Bureau Employee Consumers ’Cooperative of the Ministry of Economic Affairs 79 This paper music scale applies the Chinese National Standard (CNS) A4 specification (210 X 297 mm) A7 Β7 5. Description of the invention (77 ':

Q

X

(XCV) A,

Nhr9r10 (LXXXIX)

RyV1 〇NYN, (crc12 基基) V A2 "Please read the precautions on the back first and then fill out this page"-. Pei Dingjing uses XCV's breath, the following flowchart XLIV can be prepared where Ri is the husband A C (0) CrC4 alkyl-substituted Ci_ci2 alkyl formula] compound. Central Ministry of Economic Affairs Employee Consumer Cooperatives printed this paper with a paper form suitable for financial officials 80- (210X297 mm) A 7 B7 V. Invention Description (78

Flow chart XLIV

R 0 A ^ | / N '^ A3

Alkali (Cr% alkyl) MgCl ▼

R

Q

X

(c ^ -c ^ 2 burned base) c (〇ι-pit base) Α2

ΟII Υ Printed by a member of the Central Bureau of Standards of the Ministry of Economic Affairs, Consumer Cooperation, where R3 is SRs. The preparation of the compound of formula I allows the reaction of the acetyl chloride of formula xcv with the thiol of formula XC VI. The reaction is shown in the flow chart XL V. 8 This paper scale is applicable to the Chinese National Standard (CNS> Α4 specification (21〇’Χ 297 g · t) A7 B7 V. Description of the invention (79) ·

Flow chart XLV

R

Ο) !! C1 r8sh (xcvi)

R

SR 8 ---------— install-f (please read the precautions on the back first and fill in this page) and make the preparation of the compound of formula i whose center is CpC! 2 alkyl substituted by a CH2OR4 group The compound of formula XCVII can be reduced to form a compound of formula I in which Han 4 is a compound of formula I, and the compound of formula 1 in which R4 is hydrogen reacts with C halide in the presence of a base as the case may be. The reaction is shown in the flow chart XLVI. 4 Central Ministry of Economic Affairs終 載 局 Employee Consumer Cooperation 衽 印 说 -82- This paper scale is applicable to the Chinese Standard (CNS) A4 specification (21 〇x 297 mm)

V. Description of the invention (8〇 Α7 Β7

Flowchart XL VI

R

Y (XCVII); [Η] (Please read the precautions on the back before filling in this page.

Printed by R i ^ .N Printed by Employee Consumer Cooperative of China National Standard Falcon Bureau

Q

X

N &gt; YN, (VC12 Hsinyl) CH / h, alkyl) A2 Y z Similarly, where Ri is a Cl_cl2 alkyl group substituted with a 〇112〇 匚 (〇) 115 group, the preparation of the compound of formula I can make 1 is replaced by a CH2〇h -83- This paper scale is universal Chinese National Standard (CNS) A4 (210x297 epidemic) A7 -----__ V. Description of the invention (81 '),. &Lt; ^-(: 12 alkyl compound of formula I reacts with the halides of formula XCVIIli in the presence of a base. The reaction is shown in Scheme XL VII.

Flow chart XL VII

(VC12 Hyunji) CH20H ΧΑΛΥ α2, ο

II X1CR5 (Please read the precautions on the back before filling in this page). Pack · Alkali (XCVIII) (Xi = Cl, Br or I), 11

R A YA V1 〇

II ΝγΝ, (CfCu alkyl) ch2〇S1rs A, the center of which is a Crc12 alkyl group substituted with a CH〇 or CH (OR6) 2 group of the preparation of the formula I compound can reduce the formula XCVI] E compound to form the formula XCIX Way 'and make it react with alcohol of formula C in the presence of acid. The reaction is shown in the flow chart XL VIII 〇-84 This paper is determined according to the Chinese standard _ (CNS) 8.4 specifications (2Ι〇χ 297 male). Seeking to be printed by the Central Bureau of Standards of the Ministry of Economic Affairs. Description of the invention (82

R A7 B7

Flow chart XLVIII (XCVII) [Η] (please read the precautions on the back and fill in this page).

Q

X R IN &quot; lTN, (Ci_Ci2 alkyl) CH0 A eight A Y 2

(XCIX) Acid.

R,-»r6〇h (C) Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

Q

X

NYN, (c "c12. Burning group) CH (〇R6) 2 y, the center of which is a HC-NOR9 group substituted ^-^ ^ alkyl preparation of the formula I compound can make the formula XCIX aldehyde and formula CI Amine reaction, the reaction is shown in flow 85. The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm). V. Description of the invention (83

Graph XLIX A7 B7

Flow chart XLIX

R

/ N | j Y ^ Cl-C12 burnt group) CHO A2 (XCIX) h2nor9 (Cl)

QV ^ 丫 VN, (Cl-C12 alkyl-yl): Χ &gt; ^ ΛΥ a2 NORr

H Similarly, the preparation of compounds of formula I where Ri is a heart-substituted alkyl substituted with HC = NCOR9 or HC = NNHCONH2 allows the aldehyde of formula XCIX to react with the amine of formula CII or the hydrazine of formula cm. The reaction is shown in Flow Diagram 1. Binding *-. (Please read the precautions on the back before filling out this page) Printed by the Ministry of Economic Affairs, Central Bureau of Pricing and Employee's Consumer Cooperatives-86- This paper music scale is applicable to the Chinese National Standard (CNS) Λ4 specifications (210 X 297 mm ) V. Description of the invention (84

R A ya N, A 7 B7 Flow chart L ''

X

Y Ύalkyl) CHO Α »(XCIX) H2NCOR9; (CII)

NCOR.II 9 (please read the precautions on the back and then fill in the tc page) -install--»

R h2nnhconh2 (CHI)

Q Printed by Beigong Consumer Cooperative, Central Bureau of Standards, Ministry of Economic Affairs

X

) j nnhconh2N, / N, ^ ^ JlY (CfCu alkyl) CH — AY 2 where R〗 is the cyano-substituted heart-^ ^ alkyl compound of formula I can be prepared using standard conditions to make the amide of the formula CIV Dehydration. The reaction is shown in flow chart LI. -87- This paper wave scale is applicable to China National Standard (CNS) A4 specification (210 / 297mm)

A

Su ^ i5a A7 --B7 V. Description of the invention (85 J. Flowchart LI s

R 丫 Υ1 ο alkyl) Lh2 a2 (CIV)

-H ^ O R. (Please read the precautions on the back before filling out this page).

N γΝ, (C ^ -Cu alkyl) CN a2 Y 2 The employees of the Central Bureau of Standards of the Ministry of Economic Affairs consume Rs as alkali metals, alkaline earth metals, manganese, copper, zinc, gu, silver, nickel, money or organic ammonium cations Compounds of the formula wherein R is an alkali metal can be prepared from the formula in which the ruler 3 is 0H and / or R is hydrogen by conventional processes known in the art. The preparation of the compound of formula I can also use nitric acid to nitrate the heterocyclic phenyl compound of formula CV to form the 3-nitro-1-heterocyclic phenyl compound of formula CVI, using standard conditions to make 3-nitro-I-hetero The cyclophenyl compound is reduced to form the 3-amino-1-heterocyclic phenyl compound of the formula, and the 3-amino small heterocyclic phenyl compound is reacted with the isocyanate or thioisocyanate of LXXVIII to form the formula cvin -88-country Standard (〔\ 5) Eight 4 specifications (2 丨 0: &lt; 297 mm) V. Description of invention (86 _y · A 7 B7

The intestine or venous vein, and the isocyanide ester or thioisocyanate of formula LXXX is used to cyclize the urea or the gland to obtain the compound of formula I in which R is hydrogen, and the alkylating agent of formula V in Alkylation of the compound of formula I where 1 ^ is hydrogen in the presence of. The reaction is shown in Flow Diagram LII. Flowchart LII

HNO 3 (Please read the precautions on the back before filling out this page).

V ΰΧΧΝ〇2 X Υ (CVI) [Η] τ • -ο

X Printed by the Central Standards Bureau of the Ministry of Economic Affairs (CVII)-RNCA (LXXVIII) The paper scale is applicable to the Chinese National Standard (CNS) Α4 specification (210Χ 297 mm) A7 B7 Flow chart LII (continued), ° γΓ ' γΝγ% X Renren〆 (CVIII) ^ 2

II C1CNCA, (LXXX) Κ Please read the back ιέ ZO. Things item '苳 4 Write a wooden page installed YAγ; Χί:

Qv. / N> ^ NH T A2 test v R1X1 (V) (ΧΛ = Cl, Br or I)

R: The preparation of the starting compound of formula π in which A, Ba, and A2 are oxygen can be prepared by reacting the amine of formula CIX with sodium hypogas and sodium oxyhydroxide. The isocyanate of formula CX 'reacts the isocyanate with the amine of formula CXI to form the urea of formula CXII, which is used at -90 copies of paper size (CNS) A4 specification (2 丨 0X297mm) ^ ^ ^ J. Ο 8 Α7 _Β7 5. Description of the invention (88 ')'

N- (air carbonyl) isocyanate cyclizes the urea to form the triketone of the formula cxm, and nitrates the triketone with nitric acid. The reaction sequence is also shown in Flow Diagram LIII. Flowchart LIII 0

NH.

NaOCl / NaOH

HCO (CX) rnh2 (CXI) Η Η (Read the precautions on the back and then fill out this page). Installed., 1T Ministry of Economic Affairs Central Bureau of Privileges and Staff Consumer Cooperation. Printed by the company Ύ

R ο X Υ (CXII)

ο C1CNCO 91 This paper is applicable to China National Standard (CNS) Α4 specification (2 丨 0X 297mm) A7 B7 V. Invention description (89 y Flow chart LIII (Continued,

0 (CXIII) ΗΝΟ 3

(Please read the precautions on the back before filling in this page). The binding of the Ministry of Economic Affairs Central Standards I Industry and Consumer Cooperatives prints the preparation of compounds of formula II in which eight and A2 are oxygen and eight is sulfur can make the urea of formula CXII nitrate An intermediate compound of formula CXIV is formed, a compound of formula CXIV is reacted with a thioisocyanate of formula CXV to form an intermediate compound of formula CXVI, and a compound of formula CXVI is cyclized with a base. The reaction scheme is shown in the flow diagram LIV. -92- This paper · The standard is applicable to the Chinese National Standard (CNS) Α4 specification (210Χ 297 mm) V. Invention description (90 Α7 Β7

X

Flow chart LIV Η ΗT R ο (CXII) ΗΝΟ 3 (please read the precautions on the back before filling this page); install · Η Η

R Order Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

X 〇2ν

Ο

II

R22〇CNCS (CXV) (r22 = (γ · &lt;: 4 alkyl)

R Η 丨 Η 州 Ο S 〇 Υ (CXVI) 絵 · 93 This paper scale is applicable to China National Standards (CNS) Α4 specifications (210 Χ 297 mm) clearly stated issued '五 2 ο

Where A is oxygen or sulfur, A! Is sulfur and 8 is oxygen, the preparation of the compound of formula II can make the isocyanate of formula CX react with alkaline aqueous solution to form the amine of formula CXVII, and make the amine and the isocyanate of formula LXXVIII or thio Isocyanate reacts to form urea of formula CXVIII, nitrating urea to obtain intermediate compound of formula CXIX, reacting compound of formula CXIX with thioisocyanate of formula CXV to form intermediate compound of formula CXX, and cyclizing compound of formula CXX with base . The response is shown in the flow diagram LV. Flow chart LV (please read the precautions on the back before filling this page). Binding Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

(CXVII) RNCA (LXXVIII) -94- This paper scale is applicable to China National Standard (CNS) Α &lt; ί specification (21〇Χ 297 mm) Α7 Β7 5. Description of the invention (92 ') Flow chart LV (performance)

A

Η ΗΎ R A Y (cxvi 工 工)

HNO 3

Η H

R 22

O OCNCS (please read the precautions on the back before filling in this page).

, tT (CXV) = Longji) 2 o

HN Y

R 丨 N ^ uu A

To HN 2 2 Ro Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (CXX) Alkaline τ -95- This paper scale applies the Chinese National Standard (CNS) A4 specification (210X297 mm) V. Description of the invention (93 y

X A 7 B7 Flow chart LV (Continued j1

Y

Among them A is sulfur and eight! And the preparation of the compound of formula II where 2 is oxygen can nitrate the amine of formula CXVII to obtain 3-nitroaniline of formula CXXI, which reacts the 3-nitroaniline with the thioisocyanate of formula CXXII to form the formula of CXXIII Thiourea, and N- (air carbonyl) isocyanate to cyclize thiourea. The reaction scheme is shown in the flow diagram LVI. Flowchart LVI

X XI: (CXVII)

HNO 3 (Please read the precautions on the back before filling in this page)-installed. / -0

O ^ N Printed by the Central Bureau of Standards of the Ministry of Economic Affairs®C Industrial and Consumer Cooperatives, T ^ V ^ NH2 IX people (CXXI) RNCS (CXXII) -96- This paper is the common Chinese national standard (CNS) A4 specification (2 丨 0 &gt; : 297mm) A7 B7 V. Description of invention (94 Flow chart LVI (Continued, X v Y (CXXIII)

0 C1CNCO

(Please read the precautions on the back before filling out this page) Outfit · The Ministry of Economic Affairs, Central Standards Bureau employee consumer cooperatives printed the formula VI which is sulfur and A2 is oxygen or sulfur. The preparation of formula VI compounds can make the formula CXXIII sulfur Urea reacts with the thioisocyanate of formula CXXIV to form the intermediate compound of formula CXXV, and the intermediate compound is cyclized with phosgene or sulfur phosgene. The reaction is shown in Flow Diagram LVII. -97- The scale of this paper is applicable to the Chinese National Standard (CN'S) A4 format (210X 297mm) V. Description of the invention (95 y · A7 B7

Flowchart LVII Η Η · * Ν

R ^ cs _ (CXXIV) H?

In I-I!--F. /! 1-I 1--.-I TJ gas US. Τβ (please read the notes on the back ^: fill out this page); C (A2) C12 ▼

O ^ N The Ministry of Economic Affairs, Central Bureau of Accreditation and Employee Investment Cooperatives printed χ Υ 'A. Among them, eight and Ai are oxygen or sulfur, and A2 is sulfur, respectively. The thioisocyanate reacts to form the thiourea of formula CXXVI, so that the thiourea and the isocyanate of formula CXXVII or sulfur-98 This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 g, f)

2 Y ^ 04158 A7 _ B7 Fifth, the invention description (96 'y · Substituted isocyanate to form the intermediate compound in formula CXXVIII, and the intermediate compound is cyclized with phosgene or sulfur phosgene. The reaction is shown in flow chart LVIII.

Flowchart LVIII

NH

R ^ CS (CXXIV) (Please read the precautions on the back before filling out this page) Install Η

Printed by the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs RNCA1 (CXXVII) -99- This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) V. Description of invention (97 A7 B7 Flow chart LVIII (continued)

X Η

Yaya S HN Y (CXXVIII)

R C (A) C1 · Please read the notes on the back to fill the page

R I 02 N N, I Π R] s X Y

A «Τ The Ministry of Economic Affairs Bureau of Central Standards Employee Consumer Cooperative Printed the preparation of the starting compound of formula CV in which Q is Q1 can make the aniline of formula CXXIX and the anhydride of formula IV react in the presence of acid such as acetic acid, the reaction is shown in the flow chart LIX . 100- This paper wave scale is applicable to the Chinese National Standard (CNS) A4 specification (2 丨 0X297mm) A 7 B7 V. Invention description (98)

Flow chart LIX (CXXIX) A,

Ο Please read the notes on the back first. Item 4 Tips and Measures

The preparation of the compound of formula CV in which Q and 2 and Z is CH allows the isocyanate of formula CXXX and the amine ester of formula IX to react in the presence of a base, and can be obtained with a sulfonating agent such as Lawson's reagent or P4S1Q as appropriate The compound is sulfurized. The reaction is shown in Flow Diagram LX. -101-The size of this paper is applicable to China National Standard (CNS) A4 specification (210X 297 gala) V. Description of invention (99 A 7 B7

Flow chart LX

OCN (CXXX) A, ik R,

R OR-11 I —22 R12 (IX) (R22 = Regulation) Γΐ (Please read the notes on the back before filling this page)

X Ύ 、-»Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

R 11

The preparation of the starting compound of formula CV in which Q is Q2 and Z is nitrogen allows the iso.cyanate of formula CXXX to react with the substituted hydrazine of formula XXVIII to form the intermediate compound of formula CXXXI, and the intermediate compound and phosgene or Sulfur phosgene anti-102 This paper scale is applicable to China National Standard (CNS) Α4 specification (210 X 297 mm)

Ι ^ ΝΗΝΗΙ ^ (XXVIXI) A7 —. ^ _ B7 V. Description of the invention (100 ·) 1. Should be formed into a compound of formula CV in which Q is Q2, Z is nitrogen and 8 is> oxygen, depending on the situation The compound of formula CV in which Q is Q2, Z is nitrogen and Ba3 is oxygen is sulfided. The reaction scheme is shown in Flow Diagram LXI.

Flowchart LXI

OCN

(CXXXI) C (A4) C12 t Binding I ^ (Please read the notes on the back before filling this page) Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs -103-This paper size is applicable to China National Standard Falcon (CNS) A4 specification (2 丨 0_X 297mm) A7 B7 V. Description of invention (101) 1 process diagram—LXI (continued $ R 11 r12

X Ϊ Sulfur Brewing ▼

Printed by the Consumer Labor Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, where Q is Q11, A3 is sulfur, A4 is oxygen, and z is CH. The preparation of a compound of formula CV allows the thioisocyanate of formula CXXXII to react with the amine of formula XXV to form a formula Thiourea of CXXXIII, and react the sulfur vein with or-halogen halide of formula XXVII in the presence of base. The reaction is shown in Flow Diagram LXII. 104- The standard of this paper is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 gong) 158 A7 B7 5. Description of the invention (1〇2 ’) '

Flow chart LXII χ ν γ (CXXXII) R11NH2 (XXV) s X YA Y (CXXXIII) Please read the meanings on the back first, then write this page

1 X Η C— OMHC 1 X Order Printed by Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy r12 (XXVII) (X, = Cl, Br or I) t

Where Q is Qll, A3 is sulfur, A4 is oxygen and Z is nitrogen, the preparation of the starting compound of formula CN can react the thioisocyanate of formula CXXXII with the substituted hydrazine of formula XXVIII to form the intermediate compound of formula CXXXIV The compound reacts with phosgene or a suitable phosgene equivalent in the presence of a base such as triethylamine. -105 This paper music scale applies the Chinese National Standard (CNS) Α4 specification (210X 297 mm) A7 B7 V. Description of the invention (103 '). The reaction sequence is shown in the flow chart LXIII.

Flowchart LVIII

R

SCN

R12NHNHRn (XXVIII) Η Η12 S 丫

-I s X (CXXXIV) 絵 '

12 N

Y COC1,

, N yso X 'Clothing button- ^ C ((Please read the notes on the back before filling in this I) Printed by the Consumer Labor Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs where Q is Qll, people 3 and A4 are oxygen and Z is The preparation of the compound of the formula CV of CH can react the isocyanate of the formula CXXX with the amine of the formula XXV to form the urea of the formula CXXXV, and dehydrate the urea to form the carbodiimide of the formula CXXXVI. Halogen reaction to form halogen veins of formula CXXXVII, so that the amidines are hydrolyzed with acidic water to form brewing veins, and the veins are added in situ 106- This paper scale is applicable to China National Standard (CNS) Α4 specifications (210 X 297 mm) 5. Description of the invention (KM '/ · A7 B7

The heat 'forms the 0-brew vein of formula CXXXVIII, and reacts the O-cool with the test amine. The reaction is shown in the flow diagram LXIV. Flow chart LXIV B

Y r1: lnh2 (XXV) -TXλ X (CXXXV)

Y (please read the precautions on the back before filling in this page). Binding • h2〇τ Printed by the Employee Consumer Cooperative of the Central Standardization Bureau of the Ministry of Economic Affairs 107- This paper scale is applicable to the Chinese National Standard Falcon (CNS) A4 specification (210 X297 公 尨> ΑΊ Β7 5. Description of the invention (105 ·) W11

Flow chart LXIV (4) 〇

II X1C &lt; j: HX1 R12 (XXVII) j (Χλ = Cl, Br or I), please fill in this page first and then fill in this page

R 12 'X, 0 N—C: 1 R11

: Nxx X

Y

R Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 12, (CXXXVII) 1) h3o + 2) △ ▼

Ο 〇—C—I

R: Nxx X v 11 (CXXXVIII) base t

Y -108- This paper scale is applicable to the Chinese national standard (CNS> A4 specification (2lOX297mm>) ㈣! 53 V. Description of the invention (106 ·: Γ Α7 Β7 Flow chart LXIV (碹)

&quot; 11 X

The present invention also relates to an intermediate compound that can be used to prepare a compound of formula I, which has the structural formula CXXXIX

R (CXXXIX) Fill in the pages of Fangtai where T is NH2, -NCO, -NCS, -N3, -NHNH2, -NHC (S) NHRn, -C (〇) NHNHR13, -C (0) H, -C (0) CH3, -C (0) C02 (CrC4 alkyl), -C (0) CH2C (0) Rn, -C ^ OKi ^ CKAjCKCVC ^ alkyl), -C02 (CrC4 alkyl), -N = C = NRU, -NHC ^ CONHRn, -NHC (S) NR11HNR12, -N = C (SCH3) NHRU, -NHC02 (Cr C4 alkyl), -C (Cl) = NOH, Employee Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs Printing

-109- This paper uses the Chinese National Standard (CNS) Λ4 specification (2 丨 0 X Z97mm) A7 B7 5. Description of the invention (107 '). X and Y are hydrogen, halogen, nitro, Cyanogen, crc4 alkyl, crc4 haloalkyl, C "C4 alkoxy, CVC4 haloalkoxy or S (0) mR2; m is an integer of 0, 1 or 2, · heart is ^-^ alkyl or Haloalkyl group; R is hydrogen, CVC6 alkyl group, c2-c12 alkoxyalkyl group, c3-c12 alkylcarbonylalkyl group, C3-Cj2 Huaxuanji burning group 'C3-C12 pit oxygen Ji · Tongji' 匚 3_ Phenyl 12-tooth burnt carbonyl alkyl, c3-c6 alkenyl, c3-c6 monoblock, optionally substituted with one to three halogen, crc4 alkyl, crc4 alkoxy or Crq haloalkoxy substituted phenyl, or as In the case of one to three halogen, crc4 alkyl, crc4 alkoxy or C1-C4 alkyloxy substituted benzyl;

Ri is hydrogen, C3-C6 alkenyl, C3-C6 alkynyl, cyano, optionally via one or more functional atoms, or a gas group 'C (0) R3' 〇c (o) r5, ch2oc (o ) r5, or4, ch2or4 or cr6 (〇r7) 2 group or one optionally substituted by one to three halogen, CrC4 alkyl, Cr c4 alkoxy or (^-(^ haloalkoxy substituted phenyl ci · C 12 burned base; or printed by the Cooperative Society for Expenditure of Employees of the Central Standards Bureau of the Ministry of Economic Affairs, optionally substituted with one to three halogens, C ^ -C # burned base, Ci-Cj tiger milk base or Cl-(^ halogenooxy Phenyl; R3 is OR8, SRptNR9R10;-R4, ruler 5 and Han 6 are each hydrogen, Ci-q alkyl or Crq South alkyl; R7 is C "C4 burned group; ruler 8 is optionally alkoxy Group '(^-(^ alkylthio'halogen'hydroxy group, C3-C6 cycloalkyl group, squeeze group or optionally one or more dentin's) Applicable scale is applicable to Zhongyuan (CNS) _Λ4 specification-110- (2 ΙΟ X 297 mm) 51 A7 --------- _____ B7 .............. V. Description of the invention (1Q8.) ·. Cyanide Phenyl group, Shi Xiaoji, C ^ -C ^ appearance group, ^ i-C4 halo group, ^-^ emulsyl group or Ci_C4 halo oxy substituted phenyl group Substituted radicals; optionally CrC4 alkoxy, halogen, 〇: 3-06 cycloalkyl or optionally name k — or more halogens, ambience, Shi Xiaoji 'c 〖-C4 halo, Cj_C4 haloalkyl , C3-C6 alkenyl substituted by phenyl substituted by crc4 alkoxy or c 〖-c4 haloalkoxy; optionally C3-C6 alkynyl substituted by icrc4 alkoxy or halogen; (: 3-(: 6 Cycloalkyl; Ruler 9 and Han 10 are each hydrogen, Ci-C ^ alkyl, optionally via one or more halogen, cyano, nitro, Cl_C4 alkyl, C1-C4 haloalkyl, Ci- C4 alkoxy or halogenated ^ halo alkoxy substituted zigzag group; or optionally one or more halogen, cyano, nitro, (^-(: 4 alkyl, CrC4 halogen appearance group 'crc4 oxy oxygen Phenyl group substituted by a halogen group or crc4 halooxy group; the ruler "and ruler ^ are each hydrogen, optionally Ci-C ^ burned group substituted by one or more halogen atoms, or optionally substituted by one or more halogen atoms The substituted C3_C6 cycloalkyl group, and when the ruler ^ and! ^ 2 are combined with the atoms to which they are attached, it can represent that there are 0, S (0) r4 N inserted as the case may be and the Shen Shenjing-up to three A 4- to 7-membered saturated or unsaturated with one or more functional atoms Ring: R13 is hydrogen, ^-(^ burned group or C ^ -C ^ halo-hyunyl group; A, A i, A2 and A3 are respectively 0 or S; and -111-(jingxian read the back: ^ meaning Please fill in this page again. -Installed--3 t This paper scale is applicable to the Chinese national standard falcon (cns> A4 specifications (210X297 mm> ύ ^ 4Ι〇β Α7 Β7. Fifth, the invention description (1〇9 · Γ. R It is an integer of Ο, 1 or 2. 'The preferred intermediate compound of formula CXXXIX is where T is NH2, -NCO, -NCS, -N3, -NHNH2, -NHC (S) NHRU, -NHCWNHUu, -NHCCSWRuNHRM-N ^ CtNR ^; X is hydrogen or dentin; Y is hydrogen, autogenous, nitro or cyano; R is hydrogen, Crh alkyl, CrC4 alkoxymethyl, (Crc4 alkoxy) carbonylmethyl, C3-C6 alkenyl or C3-C6 alkynyl;,

Ri is hydrogen 'C3-C6 alkenyl' C3-C6 alkynyl or CrC6 alkyl optionally substituted by a co2r8; alkyl; one foot 11 and one foot 12 are each hydrogen or CpC: 4 alkyl, and When Rn and ri2 combine with the atoms to which they are attached to form a ring, where RUR12 is optionally substituted with s (o) r and optionally substituted with one to three methyl groups or — or multiple halogen atoms — : 5 alkylene; A, eight! And eight 2 are 0; and r is an integer of 0, 1 or 2. The intermediate compound of the better formula of the present invention is CXXXIX intermediate compound, which is printed by Beigong Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs nh2 '-NC0, _NCS, -nhqswhRvVnhc⑼NHRn; X and Y are each hydrogen, F or Cl; R is hydrogen, CrC4 alkyl, Crq alkoxymethyl, (Ci_C4 alkoxy) carbonylmethyl' allyl or block Propyl

Rl is argon 'propyl, propargyl, or C! -C4 alkyl substituted with one C〇2R8 as appropriate: ---_- 112- This paper scale is applicable to China National Standard (CNS) A4 specification (2lOX297 Mm) A7 ___ — ___B7 V. Description of the invention (110 ′) · Ruler 8 is Ci_C4 pit base; Rji is chlorine or C! -C4 burning base; and A, A2 is 〇. The invention also relates to intermediate compounds having the structural formula CXL

(CXL) X

τι Y -------- · "Installation-(Please read the precautions on the back before filling out this page) Printed by the Monthly Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs ^ T # N02, NH2 or -NHC ( A) NHR; A ', A3 and A4 are respectively Ο or S; X and Y are respectively hydrogen' halogen, nitro 'cyano, CrC4 alkyl, crc4 haloalkyl, cvq alkoxy, Cl_c4 haloalkoxy Radical or s (〇) mR2; m is an integer of 0, 1 or 2;, is a dagger-daggeralkyl or crc4 haloalkyl: R is hydrogen 'CrC6 alkyl, C2-C12 alkoxyalkyl, c3-C12 Alkylcarbonyl 'C3-C12 self-regulated · carbonylalkyl' c3-c12 alkoxy condensed alkyl, c3-c12 haloalkoxy group · C3-C6 alkenyl, c3-C0 block, depending on the situation One to three halogens, c ^ -c ^ alkyl, (^-(: 4 alkoxy or Crq haloalkoxy phenyl group, or optionally one to three halogens, c 丨 -c4 alkyl ' crc4 alkoxy or CfC # halo-oxygen substituted naphthyl; -113- The paper scale is applicable to the Chinese National Standard (CNS) Λ4 specification (210X29? Gongqing) 5. Description of the invention (Chuan ·) *-A7 B7 R11 And R12 are hydrogen, respectively, and C _Γ substituted with one or more halogen atoms depending on the situation C ^ ^ 〇 ^ ^ 3 which is substituted by halogen atoms, and when ^^ and! ^ 2 the atoms to which they are attached are combined, 0, S (0) j ^ N and As the case may be, _ 'means "," the 4_ to 7_ member saturated or unsaturated products substituted by two female atoms or multiple atom atoms of Gong or R is an integer of 0, 1 or 2. Yi' and more A preferred compound of the formula CXL is where NH2 or -NHC (0) NHR; a3 and octa 4 are 0; X and Y are each hydrogen or _ element; R is crc6 alkyl, c3-c6 alkenyl or c3_c6 block ; &Amp; 11 and 1112 combine with the atoms to which they are attached to form a ring, where R, *: the secret λ ancient Q, PT 40 up to, 〇Λ.Τ! o) ra depends on the situation Shen Jing — to three 曱 — Cheng or — or multiple halogen atoms substituted C2_C, environment group, or RllRu formula: (please read the notes on the back if fill in this page)-Pei, · 5T printed by the Ministry of Economic Affairs Central Standardization Bureau of Consumer Labor Cooperatives CRi9-CR2〇 = CR2i-represented, wherein the government is argon, halogen or methyl; and r is an integer of 0, 1 or 2. The better formula CXL The intermediate compound is T # N02, NH2 or -NHC (0) NHR, · A3 And A # is 〇; X is F or C1; Υ is C1; ruler is CrCU alkyl, allyl or propargyl; and 18

, RC ^ 18 = 19, I hate 2〇 and: R2l each: -114 This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 5. Description of the invention (112 y. A7 B7 Central Ministry of Economic Affairs Printed by the Bureau of Standards, Shell Industry and Consumers

Ru &amp; Rl2 is combined with the atoms to which it is attached. ^ T K11 Han 12 is an butyl group substituted with one to three methyl groups as the case may be. The compound of the formula I of the present invention is cocoon c A, which is used to control a wide range of unwanted plants (effective herbicides. These compounds can effectively control the miscellaneous in dry arable land and fish farming area The compound can also be used as an aquatic herbicide and each is applied to its case at a rate of about 0.016 to 4.0 kg / h and preferably 〇32 to 20 kg / hectare or to seeds or other propagation Organisms such as buds and roots, tubers or rhizomes are effective in controlling the above-mentioned plants. The compounds of formula I of the present invention are most suitable as herbicides with a broad spectrum, especially when applied to the post-germination area of weeds to be controlled. Certain compounds are selective. In fact, some compounds of the present invention are selective for crops such as soybean, rice and corn. Although the compound of formula i of the present invention can effectively control unwanted plant species when used alone, it can also be used with other compounds Biochemicals are used in combination, including other herbicides. The compound of formula I of the present invention can be applied to the herbicide composition in a solid or liquid state until it includes a herbicidally effective amount of disperse or falls in agriculturally acceptable inertness. . Solid fear or liquid. The compound in the carrier. The composition can be treated before or after germination. The compound of formula I can be formulated into an emulsifiable concentrate, a wettable powder, a granular formula, and can be flow concentrated In order to improve the understanding of the present invention, the following examples are mainly used to describe more specific details. The present invention should not be considered to be limited by this example to define the scope of the scope of the patent application. NMR-word means nuclear magnetic resonance spectrum. Please Read the first 5 pages on the back and then fill in β %%. Tai Bing Bin Mingming Mingzhong 115- This ... The Zhang scale is applicable to the Chinese National Standard Sheep (CNS> "Xiange (2! () ./ 297 Gongqing). I, A7 B7 V. Description of the invention (彳 13 '), Example 1, Preparation of 1- (2-dichloro-1-phenyl) methylurea

F ^ YC. Gas + NaOCl + NaOH + CH3NH2 (read the notes on the back first and then fill in this page). Install 50% sodium hydroxide solution (28 g '0.35 mol) printed by the Central Standard Falcon Bureau Employee Consumer Cooperative of the Ministry of Economic Affairs A mixture of 5% sodium hypogaseous solution (226 ml) was added to 2, _gas_4, -fluorophenylamide (50 g, 0.288 mol) in a mixture of methanol at 0 ° C. After β addition was completed, 〇〇c add 55 ml of 40% methylamine solution. The resulting reaction mixture was heated to 5yC and stirred at 55 »c for 6 hours, cooled to room temperature and filtered to obtain a solid. The solid was washed sequentially with water and hexane and dried with air to give the target product as a white solid (30 g, mp 174-178 ...). Use essentially the same procedure, but the 2, _gas_4, _fluorobenzamide is replaced with 2,4, _difluorobenzylamine to give 1- (2,4-difluorophenyl) as a beige solid ) -3-methylurea. Example-2 1-. (J, _4_ιdi_fluorophenyl) -3 -methylurea

+ CH, NCO • Order

F

F 116 Standards (CNS) from specifications (2lQx29? Public issue Η Η ~ 雅, CH:

F 0 ΑΊ ΑΊ; ΧΪ: • CH- Β7 V. Description of the invention (114) 1. Add methyl isocyanate (9.6 in a toluene solution containing 2,4-difluoroaniline (15 g, 0.116 Mjf :)) G, 10 mL, 0.174 mol), the reaction mixture was stirred for 1 hour and filtered to obtain a solid. The solid was washed with hexane and dried with air to give the target product as an off-white solid. mp 182_183 ° C. Using essentially the same procedure, but using the appropriate substituted aniline, the following compounds are obtained: Η Η τ Ο Please read the meanings of the details at your leisure. Fill in this page Install υ Ν〇2 Η

X Η F Υ F C1 mp ° C 229-232 Order Example 1- (2-Gas_4 · Fluorophenyl) -3 -methyl-s-Sanhu-2,4,6 (111,311,5 £ [) -Preparation of three heirs Η Η Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economy XXX CH:

οI! + C1CNCO

j〇n F Cl N- (chlorocarbonyl) isocyanate was added to the toluene mixture containing l- (2-chloro-4-fluorophenyl) _3-methyl vein (29.2 g, 0.144 mol) (18.97 grams, 0. ISO moles). The reaction mixture was stirred for 90 minutes and filtered to obtain the standard of white solid -117- This standard is suitable for the Chinese National Standard Falcon (CNS) A4 specification (2 丨 0 侂 297mm) A7 -___- _B7_ (115.) The product of 4, (32_1 g, mp 225-228Ί :). , Using essentially the same procedure, but using the appropriate substituted glands, the following compounds are obtained:

UXY mp ° c Η F --F 242-245 Η Cl Cl 200-204 Ν〇2 HF 180-183 Example 4 l _- (2-gas-4-fluoro-5-nitrosyl) -3-methyl- s-Sanken-2,4,6ΠΗ.3ΤΤ 5m Preparation of three ketones (please read the notes on the back first and then fill out this page). Installed,, 11 Printed by the employee cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

HNO 3 h2so4

In concentrated sulfuric acid solution containing H2-Gas-4-fluorophenyl) · 3-methyl-Shiba-Sanxi-2,4,6 (1H, 3H, 5H) -S ketone (32_4g, 0.119mol) Add nitric acid (70% actual, 8.3 ml, 0.13 mole) while maintaining the temperature of the reaction mixture low. After the addition is complete, the reaction mixture is stirred at room temperature for 30 minutes, and cooled to 忉 -118- The standard of this paper is applicable to the Chinese National Standard (CNS) Λ4 specification (210X297 male seat) A7 _____B7 V. Description of the invention (116.) · . ° C and diluted with ice water. The resulting aqueous liquid mixture was filtered to obtain a solid, which was washed with water and air-dried to obtain the target product (28.5 g, 1111) 135_139 as a white solid. (:) 〇 Using essentially the same procedure, but using the appropriate substituted 1_phenyl_3_methyl tridecene-2,4,6 (111,311,511) -trione, the following compounds are obtained:

X Y ___ 〇e! C_ F F. 100-120 C1 C1 220-222 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

1- (2-Gas-4-fluoro-5-nitrophenyl) -3-methyl-chromo-tri 11 well-2,4,6 (1H, 3H, 5H) -trione (28.5 g, 〇. 〇9mol) and 5% platinum / activated carbon (1g) mixed with ethyl acetate 119- Table paper music standard is applicable to China National Standard (CNS) A4 specification (210X 297 male) Λ7 V. Invention description (^ 丨 物Hydrogenation at 55 psi until the nitrogen absorption is complete., &Amp; The reaction mixture is filtered and concentrated in the air to obtain the product of the standard as a white solid. Mp 244-245Ό. Use essentially the same procedure, but use, % Qiaosong is substituted with 1-nitrophenyl-3-methyltris--2,4,6 (1H, 3H, 5H)-= '~ Steel' to get the following compounds ·· Ha XF Cl Η

Υ F Cl F -pp-! C_ 194-196 145-151

Example of Yingan, Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 6 υ ^: 2-Fluoro-5- (hexahydro-3-methyl-2 ^^ Sanqi-based_s_Sangeng-Buji) Maoji] -1 -Cyclohexyl-1.2-dioctidine

+ 〇

-120- The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210 + 297 mm) V. Description of the invention, A7 B7 1- (5-amino-2-gas_4_ fluorophenyl) _3_ methyl Sanken_2 4 6 (1h, 3H, 5H) _ one ketone (2j_4 g, 0 0816 mol) and 3,4,5,6-tetrahydro-anhydride (13.〇4 g '0 0857 mol) The mixture in glacial acetic acid was stirred at 100 ° C for 8 hours, cooled to 25 ° C and poured into water. The resulting aqueous-liquid mixture was filtered to obtain a solid, which was washed permanently and dried in a flood box 2 to obtain the target product as a beige solid (22.5 g, mp 154-165 ° C). Using essentially the same procedure, but using the appropriate substituted 1_ (aminophenyl) _3_methyl_color · Sanwei_2,4,6 (111,311,511) _trione, the following compounds are obtained:

X (Read the notes on the back of the poem before filling in this page). Binding X F C1 Η

Υ F Cl F

mp ° C 135-150 125-135 VIt Printed example of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 7 Hexene-1.2-diyl-imino) -4-fluoromoso_s-sanken • acetic acid Tributyl ester ^^

This record standard Tongcai_Home Fresh (CNS) Cong Mi (21Qx297 Gong Mei -121-V. Description of the invention (119 · y. A7 B7

1- [4-Gas-2-fluoro-5-hexahydro-3-methyl-2,4,6-trioxy_Shiba-San 11 well-; 1-yl) phenyl] -1-cyclohexyl A mixture of ene-I, 2-bis-pyramideimine (8 g, 0.0199 mol) and potassium carbonate (4.13 g, 0.0299 mol) in N, N-dimethylformamide to tert-butyl bromoacetate (5.82g, 0.0299mol) Process, stir at room temperature, mix for 18 hours and pour into water. The resulting water-liquid mixture was filtered to obtain a solid, which was washed with water and air-dried to obtain the target product as a white solid (6.13 g, mp 105-11 5 ° C). Use essentially the same procedure, but use the appropriate substituted 1- [5- (hexahydro-3-methyl-2,4,6-trioxytrigen-1-yl) phenyl] -1-ring Hexene-1,2-dicarboximide and suitable alkylating agent, the following compounds are obtained: (Please read the precautions on the back before filling this page) -Pack- · νδ CH.

Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs X o YX Υ 5i mo ° c FF • ch2co2ch3 100-115 F Cl ch2co2ch3 95-110 C1 Cl CH2C02C (CH3) 3 95-100 C1 Cl ch2co2ch3 120-125 Η F CH2C02CH3 110 -120 F Cl ch2ch = ch2 91-106 F ci CH2ChCH 105-122 -122 t paper size is applicable to Chinese national standard (2 丨 〇: &lt; 297 mm) V. Description of invention (120) A7 B7 Example 8 Gas-5 -(1-cyclohexyl-1,2-diokilimide) -4-fluorophenyl 1 tetrahydro-5-methyl-2,4,6-trioxy-5-trioxa-1 ( 211) -Preparation of acetic acid

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

.1T Printed 3- (2-Gas-5- (1-Cyclohexene-1,2-Dicarboximide) -4-fluorophenyl] tetrahydro-5 by the Employee Poverty Alleviation Cooperative of the Ministry of Economic Affairs -Methyl-2,4,6-trioxytrigen-1 (2H) -tert-butyl acetate (5.92 g, 0.011 mol) in trifluoroacetic acid solution was refluxed for 2 hours, cooled to room temperature and emptied Concentrate to obtain No. sapphire gum. The gum is dissolved in ether, and the resulting solution is concentrated in the air to obtain the target product as a yellow solid (3.62 g, 11 ^ 75-80 ° (:). Example 9 3- 『2-gas -5- (1-cyclohexene-1,2-dicarboxy-imino) -4-fluorophenyl 1 tetrahydro-5-methyl-2,4,6-trioxy-3-tri Preparation of Geng-1 (211) -isopropyl acetate

ch2c〇2h 十 3ΧΗ (α ^) 2 + K2C〇3 -123 This paper scale is applicable to the Chinese National Standard (CNS) A4 specification i 210X297 mm) kl B7 ύ ^ 4ί〇β V. Description of invention (121

CH2C〇2CH (CH3) 2 3- [2 · Ga-5- (Bucyclohexene-1,2-dicarboxylimide) _4 • fluorophenyl] tetrahydro-5-methyl-2,4, A solution of 6-trioxy-chromo-tri-well acetic acid (1-5 g, 3.13 mmol) in N, N-dimethylformamide with 2-iodopropane (0.849 g, -5 mmol) and Treat with potassium carbonate (0.69 g, 5 mmol), stir at room temperature overnight and pour into water. The resulting aqueous mixture was filtered to obtain a solid, and the target product (0.6 g, mp 100-13 CTC) was obtained as an off-white solid after air-drying. Example 10 Preparation of N 『(4-gas-3- 绡 苽 墓) amine methyl] glycine ethyl ester

NCO + NH2CH2C〇2CH2CH3 · HC1 ten N (CH2CH3) 3

Printed by the Employees ’Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Η Η Τ Τ CH2C〇2CH2CH3 Ο Isocyano 4-fluoro-3-nitrophenyl ester (10 g '· 0.055 mol) in anhydrous tetrahydrofuran solution cooled to o ° c, treated with glycine ethyl ester hydrochloride (77 g, 0.0055 mol), treated with triethylamine (5.56 g, 0.055 mol) while maintaining the temperature below 1 (TC, stirred at room temperature for 1 hour Pour into water. The water-liquid mixture is extracted with acid. The combined organic extracts are washed sequentially with 1N hydrochloric acid and table salt. I wash Su-124- The standard of the paper is applicable to the Chinese National Standard (CNS) 8.4 (U10X 297 mm) B7 V. Description of the invention (122_;) '' Dried with anhydrous magnesium sulfate 'and concentrated in the air) to obtain a solid. After air drying, the target product (8.8 g, mp 115_12〇.) Was obtained as a yellow solid. (:). Example 11 Preparation of 3-amino-4-fluorophenyl) aminecarboxamide 1 glycine ethyl ester η

] | CH C〇2CH2CH3 + Pt / C + H

H.N

F

Η H 丫 _ch2c〇2ch2ch3 0 N-[(4-fluoro-3_nitrophenyl) aminomethyl] glycine ethyl ester (8 g, 0.029 mol) and 5% platinum / activated carbon (0.5 g) in The mixture of ethyl acetate was hydrogenated at 50 psi until the hydrogen was completely absorbed. The reaction mixture was then filtered and cooled in an ice bath until a solid formed. The solid was collected by filtration and air-dried to obtain the target product as a white solid (4.5 g, mp 1 52-153 ° C). Example 12 Preparation of m- "3- (l-cyclohexene-1,2-dicarboxyimidimide) -4-fluorophenyl 1aminoformamide} ethyl glycine *

__- 125- This paper scale is applicable to Chinese national standard (CNsl Λ4 specification (210X297mm) A7 B7 V. Invention description (123, y

Η Η nY ^, ch2c〇2ch2ch3 Ο

F N-[(3-Amino-4-fluorophenyl) aminecarboxamide] glycine ethyl acetate (4 g, 0.0157 mol) in acetic acid solution with 3,4,5,6-tetrahydrophthalic anhydride ( 2.43g, 0_〇16mol) treatment, heated at 10 (TC 8 hours, cooled to room temperature and poured into water. The resulting aqueous liquid mixture was filtered to obtain a solid, which was recrystallized from ethyl acetate 7 hex boiling liquid , To obtain the target product of a yellow solid, mP 72-82 ° c. Example 13 3- (3- (1-cyclohexene-1,2-difluoroamide imine V4-fluorobenzene steaming f Please read the back first Things to pay attention to fill this page}

F 〇 Set the Central Standards Bureau of the Ministry of Economic Affairs

{N

F (1 Cyclohexyl · 1 2-Diaminoamine fluorophenyl] amine methyl] Glycine-126- This paper is suitable for the standard of China National Citron (CNS) Α4 specification (J 0 κ －97 — Shen) A7 3〇4158. ___B7 5. Description of the invention (124'Γ ·. Ethyl acetate (2.45g '6.3¾ mole) in toluene with isocyanate n_ (gas carbonyl) vinegar (0.77g, 7.3 mmol Ear) treatment, stirring for 12 hours at 60 ° C and concentrating to obtain a solid. The solid was dried in an empty oven at 85 ° C for 24 hours to obtain the target product as a yellow solid ⑵: ^ g,! ^ .;-; ^. ^ ). Example 14 5- (3- (1-cyclohexene-1,2-dicarboxylimide V4-pyrophenyl 1 dihydro-K6- ^ oxy-s-tris-1,3 (2H , 4H) -Preparation of ethyl tert-butyl diacetate

Tert-Butyl bromoacetate (0.689 g, 3.5 mmol) and potassium carbonate (0.484 g, 3.5 mmol) were added to the 3- [3- (1-cyclohexene-I, 2-dicarboxyl) Imine) -4 · -fluorophenyl] tetrahydro_2,4,6_trioxy-chromo-three-well-1 (2H) -ethyl acetate (1.35 g, 2.9 mmol) N , N-dimethylformamide solution. The resulting reaction mixture was stirred at room temperature for 18 hours, poured into water and extracted with ether. The organic extracts were combined and washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the target product (0.8 g, mp 95-105T) as an amber solid. -127- This paper scale is applicable to China National Standard Falcon (CN.S) A4 specification (210X 297mm)

· · -I (please read the back page first: 4 to write this page) A7 B7 printed by the Poverty Alleviation Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs V. Invention description (125 ·). Example 1 5 Gas 4: Mao Tetrahydrogen -5 • 甲某 _2 4 β · 三 望 基 _s_ 三 咕 1ί_2Η) -Isopropyl acetate

CH 3 Ah NH + BrCH2C〇2CH (CH3, + K2C〇3

F

Cl CH- (please read the notes on the back before filling in this page) 'Install W ° CH2C〇2CH (CH3) 2

, 1T ketone

Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs $ L 1- (2-Gas-4-fluorophenyl) -3-methyl- £-三 啩 _2,4,6 (1Η, 3ϋ, 5ίί)-(40_9 G '0.150 mol)' potassium carbonate pi'g, 0 225 mol) and bromoacetic acid iso-contaminated ester (29.1 ml, 0.225 mol) in a mixture of Ν, Ν-dimethylformamide at room temperature 2 Hour, poured into water and extracted with ethyl acetate. The organic extract was washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an oil. Use glue and 〇〇 /. To 丨 〇〇 /. The solution of acid in two-gas methane burns was subjected to flash column chromatography to obtain the target product as a white solid (515 g, mp 127-128 ...). Example 16 _5 · Nifedipine) Zhu_hydro-5_methyl-2 ~ 6 · trioxy_s_tri ^^ _1_ (2H) -acetic acid preparation-128- Λ7 V. Description of the invention (126, ) '.

F f | T TCH2C〇2CH (CH3) 2

+ HNO 3

ch2c〇2h Please read the notes on the back I ^ 3- (2-Gas-4-fluorophenyl) tetrahydro_5_methyl_2,4,6 printed by the Employee Consumer Cooperative of the Central Department of Economic Affairs of the Ministry of Economic Affairs _Trioxy + three whistle _ 1 (2Η)-. Isopropyl acetate (48.7 g, 〇〇〇〇〇〇〇8mol) was cooled in a solution of concentrated acid to 0C &amp; 9〇 /. Slightly acidic (26 ml) treatment, at room temperature to give overnight, 90 /. Treat with nitric acid (10 mL), stir for 4 hours, treat with nitric acid (20 mL) ', stir overnight at room temperature, treat with 90% nitric acid (10 mL), stir for 1 hour, and pour on ice. The resulting aqueous solution was filtered to obtain a solid. The solid I solution in ether was dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the target product as a yellow foam, which was identified by NMR spectral analysis. _Example 173 "-(2dioxo_ ^ ·: gas-5-nitrophenyl) tetrakis-5-5 · methyl · 2,4,6_trioxy_s_triρxiandi U2H) -acetic acid Isopropyl ester-

CH 〇 丫 ~ 丫 〇 3 Ο ^ Ν

CH2C〇2H + H2S〇4 +

(CH3) 2CHOH 1Τ -129- This paper uses the Chinese National Standard (CMS) A4 specifications (210Χ 297mm). 5. Description of the invention (127 · ί A7 B7

3- (2 · chloro-4-fluoro-5-nitrophenyl) tetrahydro-5-methyl-2,4,6_trioxytrip-1 (2Η) -acetic acid (43.6 g, 0.105 mol Ear) and concentrated sulfuric acid (25 ml) in 2-propanol (300 ml) were refluxed for 12 hours, cooled to room temperature and filtered to obtain a solid. The solid was dried to obtain the target product as an off-white solid, which was identified by NMR spectroscopy. The filtrate was partially concentrated in the air and poured onto ice. The resulting aqueous liquid mixture was extracted with ethyl acetate and the organic extract was dried over anhydrous magnesium sulfate to obtain an orange oil. The solution of silica gel and 2.5% to 5% ether in methane gas was used for flash column chromatography to obtain the target product of yellow foam. Example 18 4- (5-Amino-2-gas-4-fluorophenyl) tetrahydro-5-methyl-2,4,6-trioxo-s-sanken-U2H) -isopropyl acetate Preparation CH. (Please read the precautions on the back before filling out this page). Printed by the Staff Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

O ^ N

CH. I 3

The paper scale is applicable to the Chinese National Standard (CNS) Α4 specification (210Χ 297 mm) V. Description of the invention (128 ·) 'A7 B7 3 (2 ~ gas-4-fluoro-5-nitrophenyl) tetrahydro_5_ Hydrogenation of a mixture of methyl, 2,4,6_trioxy_color_tri 4_ (Ή) isopropyl acetate (34-8 free, 0.0835 mol) and 5% platinum / carbon (3.48 g) in ethyl acetate Hydrogen is absorbed up to about 90 psi. Next, the reaction is quenched and concentrated to obtain a foam. The foam column was chromatographed using a solution of silicone and 10% to 200 / 〇 ether = one gas methane to obtain two compounds • ^ page foam. A mixture of foam and 5% platinum / carbon (35 g) in ethyl acetate was hydrogenated to 5 psi and hydrogen was absorbed. Next, the reaction mixture was filtered and concentrated to obtain the target product of yellow foam, which was confirmed by NMR spectrum analysis. Example 19 Enzyme phenyl) tetrahydro_5_methyl_2, 4 6_Sanqi_s_isopropyl acid syrup Η.Ν

CH2C〇2CH (CH3) 2 + Λ

Cl Cl

-o Cl Printed bags for employees' consumer cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

0 = C = N

雅 CH2C〇2CH (CH3) 2 3- (5-Amino-2-gas-4_fluorophenyl) tetrahydro_5_methyl-2,4,6_trioxy_s_Sangen-1 (2H) -Isopropyl acetate (4.0g, 0103mol) in toluene was treated with 1.93M phosgene in toluene solution (19ml) and refluxed for 3 hours. • 131-This paper size is used in China National private standard car (CNS> A4 said grid (210X 297 male thin) A7 B7 V. Description of invention (Ί29 .Γ Cooled, concentrated in the air, concentrated in toluene and concentrated in the air to obtain the target product of yellow foam, which It was identified by iH NMR spectroscopy. Example 20 3-Preparation of Thio, Liningic Acid Ethyl Ester

Br hsch2ch2nh2 + B3TCH2CHC〇2CH2CH3 + n (ch2ch3) 3

NCO-CH-CH, H 2 2 3 2-aminoethanethiol (10.0 g, 〇13〇mol) and triethylamine (36 ml, 0.260 Mohr) The warm solution in aerosol was added to the aerosol / toluene (1:16) solution containing ethyl 2,3-dibromopropionate (33.9 g '0.130 mol) in 5 minutes, and reacted The mixture was stirred at room temperature for 2.5 hours, filtered and concentrated in vacuo to obtain an orange liquid. This liquid was distilled through voids to obtain the target product as a colorless liquid. Di, l21-124eC at 3 mm Hg. Example 21 kill Oxygen 8_.aJ-Tetrahydro-1,3-DiKryl group · 1H_Borzozole 11 7 1 [1'4 Bu picture degree_: 2 (3use-cover] Tsuenki} Tetrahydro- 5_Methyl_2,4,6_ 三 氲 某 _ s- 三 〃 井 -1 (2H) -Acetyl isopropyl ester

〇 = C = N

ΎΝ,, CH2C〇2CH (CH3) 2 Cl〇

CH 3

N CO_CH-CH3 H 1 -132- t paper baht scale is applicable in § National Standards (CNS> A4 specifications (2 Ψχ 297 mm A7 B7 V. Invention description (13〇.)

CH

0 S- 3 · (2-Gas-4-fluoro-5-isocyanatophenyl) tetrahydro_5_methyl j, 4, cardiotrioxy = -1 (2Η) _isopropylacetic acid gιαι1 G, 7.5 mmol) and% thiomorpholine ga (1.44 g, 8.2 mmol) in toluene solution at room temperature for ^ hours, with a few drops of 3-thiomorpholine carboxylic acid Treated with ethyl ester, stirred overnight at room temperature and filtered to obtain a yellow solid. The resulting filtrate was dried and concentrated in vacuo to obtain an orange foam. The solid and foam were combined and chromatographed using a solution of silica gel and 10% ether in dioxane to obtain an orange foam containing two compounds. Use silicone and. . /. A solution of ethyl acetate in methane gas was used for flash column chromatography to obtain the target product of off-white foam, mp 147-155. (:. Example 22 illlAj:.!: Fluoro-5- (tetrahydro-1,3,7-trioxy-1H_0 and 4-generation: well-2 (3H) -yl) phenyltetrahydro "5-methyl -2,4,6-Tri-Krypton ten: _ i (2H) -Preparation of isopropyl acetate Printed by the Employees Consumer Cooperative of the Central Bureau of Economics of the Ministry of Economic Affairs

S CH,

-133- The size of the paper is applicable to the Chinese National Standard (CNS) A4 specification (210X 297mm) 3 Inquiry A7 ......- ....... B7 V. Description of the invention (131 ·) · .. ~ '~ 3- {2-Gas-4-fluoro · 5- [5,6,8,8 &amp; -tetrahydro-1,3-upoxy-1H-imidazo [5 jc] [l' 4] -4Geng-2 (3H) -yl] phenyl 丨 tetrahydro-5-methyl-2,4,6-trioxy_s_Sangeng · 1 (2Η) -isopropyl acetate (〇 95 g, 1.75 mmol) in methanol (10 mL) was added to pre-cool to 0-5 within 15 minutes. (: Containing a solution of periodic acid (0.38 g, 1.78 mmol) in water (10 mL). After the addition is complete, the reaction mixture is stirred at room temperature overnight, diluted with difluoromethane, followed by 1 M Ear-equivalent KHJO4 solution and saline solution were washed, dried with anhydrous sulfuric acid and concentrated in vacuo to obtain a yellow foam with silicone rubber, i 〇% chain in two gas methane burning solution and 2.5% methanol in two gas methane solution to make foam Flash column chromatography to obtain the target product as a white foam (0.59 g, mp 175-180 ° C). Example 23 Preparation of diethyl diethyl dicarboxylate 1,2-dichlorodicarboxylic acid 〇Η5〇2〇γί1 ^ Λ〇〇2Η5 + Br (CH2) 4Br + K2C〇3 Ο r ^ NC〇2C2H5-u, c〇2c2hs Ministry of Economic Affairs Central Standards Bureau employee consumption cooperation du printing 1,4- bromobutane (81.4 ml , 〇682 mol) added to 1'2-dicarbonethoxyhydrazine (100 g, 0.568 mol) and potassium carbonate (158 g, i 14 mol) in acetonitrile (600 ml) within 1 hour The resulting reaction mixture was refluxed for 6 hours, cooled to room temperature and filtered, and the filtrate was concentrated in vacuo to give a yellow liquid, which was steamed to a colorless under reduced pressure The target product of the liquid (90g, 115-120 at 0.9 mm Hg. 〇〇 ___- 134- This paper wave scale is applicable to the Chinese National Standard (CNS) A4 current form (--- A7 B7 V. Description of invention ( 132 ·) 1. Example 24 Hexahydrota 4 hydrochloride, rC〇2C2Hs I + HC1 / H_0 C〇2C2H5

A solution of NH HC1 tetrahydro-1,2-dichlorodicarboxylic acid diethyl ester (45.0 g, 0.195 mol) in concentrated hydrochloric acid (190 ml) was refluxed overnight and concentrated in vacuo to give a white solid. The mixture of solid and acetonitrile was stirred for 1 hour and filtered to obtain a solid, which was dried to give the title product as a white solid (19.5 g, mp 163. (:). Example 25 Fluoro-5-thioisoalanine phenyl) tetrahydro- For the preparation of 5-methyl-2,4.6-di-g-U2H) -isopropyl acetate, please read the notes on the back and write the form on this page. Print CH 3

SCN

Yan, ch2c〇2ch (Ch3) 2 sulfur phosgene (0.50 ml, 65 millimoles) was added to the 3- (5-amino-2-gas_4 · fluorophenyl) tetrahydro_ within 45 minutes 5_methyl_2,4,6_trioxy-Chi-Sanken- This paper scale is applicable to China National Standard (CNS) -135 Λ4 specifications (210X 297mm) 3u4158 at _______B7 V. Description of the invention (133 ·), 1 (2H) -isopropyl acetate (2.5 g, 6.5 mmol) and triethylamine (18 mL, 13.0 mmol) in tetrahydrofuran solution. The reaction mixture was stirred at room temperature for 4 hours, diluted with tetrahydrofuran and filtered, and the filtrate was concentrated in vacuo to obtain the target product as an orange oil, which was identified by NMR spectroscopic analysis. Example 26 thiocarboxamide 1 thiophene} _ tetrazolium chloride-acetic acid

+ H (CH2CH3) 3

Triethylamine (2.5 mL, 18.2 mmol) was added dropwise to 3_ (2_ 气 _4_ 气 _5_thioisoaminophenyl) tetrahydro-5-methyl-2,4,6 -Trioxyl threshing_1 (2Η) _isopropyl acetate (2.79 g, 6_5 mmol) and hexahydropyrazine hydrochloride ($$ and mmol) reacted in a mixture of methanol at the same time The material is maintained at 2〇_25, c. After the addition was complete, the reaction mixture was stirred overnight at room temperature, partially concentrated in the air, and diluted with ethyl acetate. The organic phase was separated and washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an orange foam. Use (iv) and a solution of 2.5% to 10% acid in Erqijiazong to make the bubble abrupt A7 B7

V. Description of the invention (134) · Chromatography to obtain the target product of yellow foam (2.15g, mp l〇5_ll (TC). Example 27 3- {2-gas-4-fluoro_-5- 丨 (tetrahydro · 3 · Hydrogen 1 _1Η, 3Η-Π, 3,414 oxazolidine I_3,4-al thiophen-1-ylidene) amino 1phenyl 丨 tetrahydro_5-methyl-2,4,6-trioxy Preparation of base-s-three whistle 1 -1 (2Η) -isopropyl acetate CH, Η 丫丫 0 'Κ Τ TT CH2C〇2CH (CH3) 2 + C (0) C1: (Please read the back of the first Matters needing attention before filling this page SF ^^ Cl0 CH 3

o Printed 3- (2 · chloro-4-fluoro-5-[(Tetrahydro-B-well) (2H) _yl) thiocarboxamide] phenylpropanil printed by the Employee Consumer Cooperative of the Central Standard Falcon Bureau of the Ministry of Economic Affairs Hydrogen-5-methyl-2,4,6-trioxy I triphine_1 (2H) _isopropyl acetate (150 g, 2.9 mmol) in 1,2-difluoroethane The solution was added to a 20% phosgene solution in toluene (2.pi mL, 5.6 mmol) pre-cooled to 0-5C within 20 minutes. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours, in order Wash with water and brine, dry over anhydrous magnesium sulfate, and concentrate to obtain a yellow foam. Use silica gel and 2.5% to 10% ether in methane gas to flash the foam to f column chromatography to obtain the white foam target product ( 1 18 grams, η-κπχ :). -137 This paper scale is applicable to the Chinese National Standard (CNS) Α4 specification (2 丨 〇'χ 29? Mm A 7 B7 Fifth, the invention description (135 example 28 4 dagger -2 Preparation of Dendrane

m (ch2ch3) 3 Η

Acetylene gas (24.2 ml, 0.34 mole) was slowly added to a solution of 4_gas_2_fluoroaniline (49.4 g, 0.34 mole) and triethylamine (47 ml, 0.34 mole) in tetrahydrofuran At the same time the reaction mixture is maintained at a temperature below ⑼ Torr. After the addition was complete, the reaction mixture was stirred overnight at room temperature and poured into ethyl acetate. The organic solution was washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an off-white solid. The mixture of solid in ethanol was stirred for several minutes and filtered to obtain the target product as a white solid. Example 29 The preparation of chlorofluoro_5'-nitroacetamide

_, __- 138- The paper standard Ϊ is governed by the Chinese National Standard (CMS) A4. Υ4ί58 5. Description of the invention (136y, 4, gas-2, -fluoroacetanilide (51 g, 272 mol, ear ) A mixture of concentrated sulfuric acid (100 mL) was cooled to (TC, treated with nitric acid (90% actual, 14 mL, 0300 mol) for 45 minutes, stirred for 10 minutes and poured onto ice. The resulting water-liquid mixture was filtered to obtain a brown solid, which was washed with water, dried overnight and recrystallized from a gaseous hexane / hexane (17: 1) solution to obtain the target product as a yellow solid. Example 30 Wow Vol.-4'-Gas · The key to 2'-fluoroacetamide

41-Gas-21-Fluoro-5-Acetoacetanilide (μ.2 g, ⑸ mmol) and 50 / 〇platinum / carbon (7.0 g, 20 wt / wt%) in ethanol / tetrahydrofuran (2 : 1) The mixture of solutions was hydrogenated until 28 psi of hydrogen was absorbed, then the reaction mixture was filtered and concentrated in vacuo to give the target product as a brown solid, which was determined by iH NMR spectroscopy. Example 3 1 Preparation of 1- (5 -Ethylamino-2-gas-4-fluoro-benzyl u- (2-propynyl) urea Printed by the Male Workers Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs __-139 -This paper scale is applicable to China National Standards (CNS) A4 specifications and public standards) A7 B7 5. Description of the invention (137'y · Η l)

2) HC ^ CCH2NH2 (Please read the precautions on the back before filling in this page) Ί installed 5_amino_4'-gas_2'-fluoroacetanilide (11.25 g, 55.6 mmol) and triethylamine (7.70¾ liters, 55.6 mmol) was added dropwise to the stirred solution of tetrahydrofuran containing gaseous phenyl formate (8.70 mL, 69_4 mmol) in tetrahydrofuran, while maintaining the reaction mixture at 25-30X: The temperature "After the addition is completed", the reaction mixture was stirred at room temperature for 75 minutes and poured into ethyl acetate. The organic mixture was washed sequentially with water, saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown solid. The solution of the solid in tetrahydrofuran was treated with propynylamine (9.52 ml, 139 millimoles), refluxed for 1,2 hours and poured into water. The water-liquid mixture was filtered to obtain a solid, which was washed sequentially with water, hydrochloric acid and water, and dried overnight. The target product of a beige solid. Example 32 • Printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Trioxy-3- (2-propyne farm Wg_: r

Α7 Β7 V. Description of the invention (138J.

Η h3C \ ^ n ο F Η Η XI YA Cl, II CH0C = CH + C1CNCO +

Y *, CH2CSCH Economy. Printed and printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Education 0 1- (5-ethylaminoamino-2-gas_4_fluorophenyl) _3_ (2_propynyl) urea (4 50g , 15.9¾ mol) and Ebita (2 56 ml, 318 millimoles) in methane gas were treated with isocyanate] si- (gas carbonyl) ester (1 92 ml, 239 millimoles), Stir overnight at room temperature, reflux for 90 minutes, cool to room temperature, then treat with pyridine (1.30 ml) and isocyanate (gas carbonyl) ester (192 ml), stir for 10 minutes, cool to room temperature and Filtered to a solid. The solid was washed with water and hexane in sequence and dried to obtain the target product β as a brown solid. Example 3 3 1- 丄 5 diamino-2-_gas-4-fluorophenylpropynyl) _5_ 三, 井 -2 4,6_ (1Η_ 3Η ， 5Η) · The ketone of triketone Η

HC1 c2hs〇h

This paper scale is applicable to China National Standards (CNS) M pile (210x W7mm) A7 B7 5. Description of the invention (139 ·) 1 4'-Gas-2'-Fluoro-5 '-[Hexahydro-2, 4,6-Trioxy-3,-(2-propynyl)-| _-Sanken-1-yl] acetanilide (3.00 g '8.5 mmol) and 3N hydrochloric acid (25 ml) in ethanol (50 ml) of the mixture was refluxed for 3 hours, cooled to room temperature and poured into ethyl acetate. Add 3N sodium hydroxide solution (25 ml) to the organic solution and separate the phases. The organic phase is washed sequentially with saturated sodium bicarbonate solution and brine and concentrated by 2 to obtain the target product as a beige solid (2.17 g, mp 118-121 ° C) ο Example 34-Fluoride-5_L Li 4.2 · 4,6-Trigas-3- (2-propyne Vs-Sanken-1-yl) phenyl} -1-cyclohexylamine Preparation of 1,2,2-diimide

Printed 1- (5-amino-2-gas-4-fluorophenyl) -3- (2-propyne; yl) _5_ 三 〃 井 _2 4 deaths (1H , 3H, 5H)-three worms (1.50 g, 4.83 mmol) and 3, 〇 tetrahydrophthalide g anhydride (0.73 g, 4.83 mmol) in acetic acid (3 mL) in 100. 〇Add 5 hours, cool and pour into ethyl acetate layer. The organic mixture is in order from the 7j -142- local paper wave scale to the Chinese national standard falcon (CNS) Λ4 present grid (21ΰχ297 mm) A7 B7 5. Description of the invention (140 ·), 'Saturated sodium bicarbonate solution and brine Wash> Dry with anhydrous magnesium sulfate and concentrate in vacuo to obtain a yellow semi-solid. The semi-solid flash column chromatography was carried out using silica gel and ethyl acetate / hexane (1: 2) solution to obtain the white solid target product (120 g, mp 127-135. (:). Example 3 5 K4-gas Preparation of 2-Phenylphenyl M-cyclohexene-1,2-dicarboxylimide 0

Cl

Cl Printed by the Consumer Cooperative of the Central Bureau of Samples of the Ministry of Economy 4-gas-2-fluoroaniline (19.0 g '130.6 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) ) A mixture of acetic acid (15 mL) was refluxed for 2 hours, then treated with 4-gas-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into a water / ethyl acetate mixture . The organic phase was washed sequentially with water, sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a purple oil. The solution was flash column chromatographed with Miao gum and 15% to 20% ethyl acetate in hexane to obtain the target product as an off-white solid (25.3 g, mp 81-82 ° C). -143-The standard of this paper is the General Chinese National Standard (CNS) Λ4 specification (210X 297mm) 5. Description of the invention (A7 B7 Example 3 6 M: (4-gas-5-nitrophenyl) -1-cyclohexane Preparation of ene-i, 2_dicarboximide

! Installed-lb (please read the back of the page: 1ix items and then fill out this page), τ 86.7¾ moles issued by the Central Standard Falcon Bureau of the Ministry of Economic Affairs of the Ministry of Economic Affairs) The mixture of sulfur is cooled to nitric acid ( 70% actual, 6.70 mL, 104 mmol) dropwise, while maintaining the temperature at 0-2, c ', stirring at room temperature for 90 minutes, and poured onto ice. The aqueous mixture was stirred for several minutes and filtered to obtain a solid, which was washed with water and dried to obtain the target product as a white powder (28.6 g, mp 152-155 ° C). Example 37 Preparation of gas-2-gas phenyl dicarboximide

F

. XX

Fe +

CH3C〇2H

Cl -144- This paper scale is applicable to the Chinese standard (CMS) A4 specification (210/297; I) A7 B7 5. Description of the invention (142)

Iron powder (7.30 grams, 130.7 millimoles) at 65. 〇Sequentially add to acetic acid containing N- (4-gas-3-fluoro-5-nitrophenyl) -1-cyclohexene-U2-dicarboximide (10.6 g, 32.7 mmol) (100 Ml) mixture. After the addition was complete, the reaction mixture was stirred for 10 minutes and filtered through celite. The filtrate was concentrated by emptying to obtain a dark solid. The mixture of solid in ethyl red ethyl acetate / saturated sodium bicarbonate solution was passed through Meng Yao soil and the phases were separated. The organic phase was washed sequentially with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the target product as a yellow solid. Preparation of allyl-2-. [2 · oxydi 5-ii-cycloyi ^ imino) _4_fluorophenyl 1 urea -------- · ('' Pack — (please Read the precautions on the back first and then fill out this page) Printed by the Employee Consumer Cooperative of the Central Bureau of Economics of the Ministry of Economic Affairs

F.

H C =: cHCHnNCO • Cl

CH2CH = CH2 -145- This paper wave scale is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 public celebration) A7 B7 V. Description of the invention (143 N- (5-amino-4_gas-2-fluorobenzyl) ] _Cyclohexene 1 &gt; 2_dicarboximide (3 50 g, 11.9 mmol) in toluene (25 mL) was mixed with allyl isocyanate (2.10 mL, 23.8 mmol) ) Treated, heated in paper for 21 hours, then treated with allyl isocyanate (0.53 ml), heated at 60 ° C for 3 hours, cooled to 20-30 ° C and filtered to obtain a solid, which was washed with hexane, The target product was obtained as a brown solid (3.15 g, 111 n 236-238. (:). Example 39 This 1 [5- (5- (3_ ..-propyl hexanitrogen ^^ 6- trioxo _s_ ' P Well_Buji) _4_Chlorine_2_Huiji] -1-Cyclohexyl-1,2-Dithiocarbamate

CH2CH = CH2

0II C1CNCO 碕 Read the notes on the back δ 4 Write this page Pei Ding

F

. nXXntn, ch, Cl Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economy 1-allyl-3- [2-gas-5- (1-cyclohexyl_; ι, 2-dicarboxyimidimide) _4 _Fluorine] A mixture of (2.34 g '6.21 mmol) in toluene (25 mL) was treated with a (cyano) cyanate (〇_75 mL' 9.31 mmol) at 60. Mix for 3 hours, cool to room temperature and concentrate to obtain an oil. Use silica gel and ethyl acetate / hexane (2: 3) solution to perform oil column chromatography to obtain 146 white solid. The paper standard is the general Chinese National Standard (CNS) Λ4 specification (210 X 297gm |) Benzene Acid label ο ^ 4ί〇β Α7 Β7 Fifth, the description of the invention (144 ') · The product (2.6 g, mp 130-145Ό). , Example 40 N- 丨 5- 丨 3-Isopropyl hexa &amp; -2,4,6-trioxy). 4-1-4 gas-2-fluorophenyl} -1-cyclohexyl-1 , 2-Second Linlin

BrCH2C = CH

Employee's Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Printing and Burning + K2C〇3 propargyl bromide (0.37 ml, 3.36 mmol) added to ice containing [5_ (3_allyl 7T hydrogen-2,4,6-trioxy Keshisanhu-1-yl) -4-gas-2-fluorophenyl] _ι_cyclohexanol-I, 2 · dimethanoimine (1.00 g, 2_: 24 mmol) and carbon-acid Potassium (0.62 g '4.48 mmol) in a mixture of N, N-dimethylformamide. The reaction mixture was stirred for 7 hours and then poured into ethyl acetate. The organic solution was washed sequentially with water and brine. It was dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow oil. The oil was flash column chromatographed using silica gel and ethyl acetate / hexane (1: 4) to obtain the target product as a white solid (0.60 g, mp 107-114 ° C). Use essentially the same procedure, but replace allyl bromide with propargyl bromide to give N- [4-Gas-5- (3,5-dihydropropylhexahydro-2,4,6- as a white solid Trioxy-147-The ft scale of this paper is applicable to the Chinese standard (CNS) Λ4 specification (2lOX2 &lt;) 7 gongs) A7 B7 V. Description of the invention (145 '). Three-Sangeng-Buji) -2 · Fluorophenyl] -1-cyclohexene-1, i-dicarboxyimidimide, 85〇C »Example 41 3-f2-chloro-4-fluoro-5- (3-fluorog iminium) Phenyl〗 tetragonal _5-methyl -9 a &amp; trioxy-s-tri-1 (2H)-the preparation of isopropyl acetate mp 80- CH.

NYN, I; ch2c〇2ch (ch3) 2 + Cl

F 0 CH-

(Please read the precautions on the back before filling in this page) 'Install 3- (5-amino-2-gas-4-fluorophenyl) tetrahydro_5_methyl_2,4,6_trioxy _ Diphin-1 (2H)-isopropyl acetate (1.0 g '2 6 millimoles) and 3_ fluorosulfuric acid (0.51 g' 3.1¾ mole) in acetic acid solution refluxed for 6 hours ,. —% Μ Mix with Zhi Yi for several days and pour onto ice. The resulting water-liquid mixture was filtered to obtain a solid. The solid was dried and chromatographed (silicone / 2 ″% silver carp in dioxane) to obtain the yellow, mu-labeled product, mp 119_125 ° C. Example 42 Evaluation of the herbicidal properties of the compounds after germination The following tests proved the herbicidal activity of the compounds of the present invention after germination, among which: 148 (210X 297 mm) kl Printed by the Employees ’Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs ___________B7 V. Description of the invention (146 ·) 1. Treat a variety of double-leaf and single-leaf plants with the test compound A dispersed in the aqueous acetone mixture . In the test, the seedling plants grow on the jiffy plat for about two days. The test compound is dispersed in a 50/50 acetone / water mixture containing 0.5% T \ VEEN® 20, polyoxyethylene sorbitol liver monocinnamate surfactant of Atlas Chemical Industries, Inc. It is sufficient to provide about 〇125 to 〇500 kilograms of active compound per hectare when operated through a spray nozzle at 40 psi for a predetermined time. After spraying, the plants are placed on the greenhouse platform and taken care of in a practical manner. After 4 to 5 weeks of treatment, the young-seedling plants are inspected and ranked according to the rating system described later. The data obtained are shown in table b below. If the given compound has more than one test, the data is the average value. The plant species used in these assessments are recorded with initials, common names and scientific names. The compounds used in this post-emergence herbicide evaluation and the pre-emergence evaluation of the examples below are indicated by compound number and identified by name. The data in Table 1 is recorded with a compound number. The evaluation results of herbicides are divided into boring herbicides and the classification standard (0-9) indicates that "the grade is based on the straightness of the plant, growth, deformity, size, chlorosis and the appearance of the entire plant when compared with the control group. Observer. (Please read the precautions on the back before filling in this page) s‘install

D &quot; S paper and paper music standards apply to the Chinese National Standard (CNS) A4 specification (210.X297 male seat) Fifth, the invention description (147 ') · grade 9 8 7 6 5 4 3 2 1 0 A 7 B7 meaning fully Killing, killing completely, good weeding effect, weeding effective, obvious damage, moderately effective, slightly effective, slightly effective, ineffective, not evaluated compared with the control group% 100 91-99 80-90 65-79 45-64 30-44 16-29 6- 15 1-5 0 Please read the meanings on the back first. 4'I Bookbinding and Printing-150-Pigong Consumer Cooperatives, Central Standards Bureau, Ministry of Economic Affairs-150- This paper size is applicable to China National Standard (CNS) Λ4 specification (210X297mm) A7 printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs _______ _ _B7 V. Description of the invention (彳 48 ·) '· The abbreviation of the plant and species used in the weeding evaluation. The common name and scientific name ABUTH velvet leaf velvetleaf (ABUTILON THEOPHRASTI, MEDIC.) AMBEL (AMBROSIA ARTEMISII-FOLIA, L.) CASOB (CASSIA OBTUSIFOLIA, L.) CHEAL (CHENOPODIUM ALBUM, L.) IPOSS (IPOMOEA SPP.) GALAP GALIUM APARINE ECHCG ECHINOCHLOA CRUS-GALLI, (L) BEAU) SETVI Green Foxtail Setaria (SETARIA VIRIDIS, (L) BEAU) GLXMAW Soybean (GLYCINE MAX (L) MERR CV. WILLIAMS ) ORYSAT rice, Tebonnet rice (ORYZA SATIVA, L.-TEBONNET TRZAWO winter wheat, wheat (TRITICUM AESTIVUM, CV. APOLLO CV. APOLLO) ZEAE MX corn maize (ZEA MAYS L.) (Please read the notes on the back before filling in this book Page

* 1T -151-The standard of this paper method is applicable to the Chinese National Standard (CNS) A ·} Specification (210x297mm) A7 printed by the consumer cooperation of the Central Standards Bureau of the Ministry of Economic Affairs ................. ..... B7 5. Description of the invention (149%.. .. Evaluation of compound A as herbicide compound number 1 3- [2-gas-5- (1-cyclohexene-1, 2 -Dicarboxyimido) -4-fluorophenyl] tetrahydro-5-methyl-2,4,6-trioxy-Shi-Sangen-1 (2H) -methyl acetate 2 3- [ 2 -Gas 5- (1-cyclohexyl · _1,2-diokiminyl) -4 -fluorophenyl] tetramethylene-5-methyl-2,4,6-dioxy-deficient -Tri-whistle-1 (2H) -tert-butyl acetate, 3 3- [2-gas-5- (1-cyclohexene-1,2-dicarboxyimidimide) -4-fluorophenyl] Tetrahydro-5-methyl-2,4,6-trioxytrigen-1 (2H) -acetic acid 4 3- [2-gas-5- (1-cyclohexene-1,2-tricarboxyl Acetamido) -4-fluorophenyl] tetrahydro-5-methyl-2,4,6-trioxy-zhansangen-1 (2H) -isopropyl acetate 5 3- [5- ( 1-cyclohexene-1,2-dicarboxyamido) -2-fluorophenyl] tetrahydro-5-methyl-2,4,6-trioxy-chromo-tri-B-1 ( 2H) -Methoxyacetic acid 6 3- [2,4-Difluoro-5- (1-cyclohexene-1,2-dicarboxyimidimido) phenyl] tetrahydro-5-methyl-2 , 4,6-three Yl - Color - three wells 11 -1 (2H) - acetic acid methyl ester 73- [2,4_ two gas-5- (1-cyclohexene -I, 2- dicarboxylic acyl imino) phenyl]

Tetrahydro-5-methyl-2,4,6-trioxy-Shiba-Sangen-1 (2H) -tert-butyl acetate _ I 8 5- [3- (1- 刻 Hexan-1,2 -Dibetimino) -4-gas phenyl] diazo_ 2,4,6-trioxy-accounting for three tons-1,3 (2H, 4H) -diacetic acid 1-third butyl ethyl Ester _- 152- This paper scale is applicable to China National Standard (CNS) A4 specification (210X297mm) (Please read the notes on the back first and then fill in this page -C- :: installed., V5 ^^ 4158 Α7 Β7 V. Description of the invention (150 ·) The compound number 9 3_ [3_ (1_cyclohexyl-1,2-dicarboxyimidimide) -4-fluorophenyl] produced by the consumer cooperation of the Central Standards Bureau of the Ministry of Economic Affairs Tetrahydro_ 2.4.6-dioxy-chromo-trihe-1 (2H) -ethyl acetate 10 ^^-(bucyclohexene-1,2-dicarboxyimidimide-2,4-di Fluorophenyl] -5_ methyl-2,4,6 · trioxy-sheng-tri. Well-1 (2H) -methyl acetate 11 3- [2_gas · 4-fluoro-5- (3- Fluorophthalimido) phenyl] tetrahydro_5_methyl_2,4,6-dioxytrigen-1 (2H) -isopropyl acetate 12 3- {2-chloro-4-fluoro _5- [5,6,8,8a-tetrahydro_1,3_dioxy-1H-imidazolium [5 'called [1,4], Tomb》 井 _2 (3H &gt; -yl] phenyl } Tetrahydro_5 • Methyl_ 2.4.6-trioxy-chromo-tripyr-1 (2H) -isoacetic acid Ester 13 3- {2-Gas-4-Fluoro_5 · [(Tetrahydro_3_oxy_1h, 3H_ [13 4] thiadiazolidine [3,4-a] acetaminophen) Yl] benzyl} tetrahydrolsyl_ 2.4.6-trioxy_s_triphine_1 (2H) _isopropyl acetate 14 3- [2-gas-4-fluoro-5- (tetrahydro Trioxy_1H_imidazolium [51_c] [l, 4K p-well) phenyl] tetrahydromethyl · 2,4 6 · ι-oxygen-Sangen-1 (2Η) -isopropyl acetate 15 Ν-Η- 气 -2-fluoro-5- [hexahydro_2,4,6-trioxy_3_ (2_propynyldi-1--1-yl) phenyl} -1_cyclohexene Dicarboximide 16 NH-gas-2-fluoro-5- [hexahydro_3_methyl_2,4,6_trioxy_5_ (2_propynyl) tris-1-yl ] Phenylcyclohexene dicarboximide 17 N- [5- (3-allylhexahydrolmethyl-2,4,6_trioxystri_ + yl) -4-gas-2 -Fluorophenyl] -1-cyclohexyl dicarboximide ________- 153- This paper scale is applicable to the Chinese National Standard (CNS) Alpha standard (2 丨 ο 29? Public advantage) (Read the note on the back before reading Please fill out this page again.) • I-II-. 5. Description of the invention (151 Γ Compound No. 18 19 20 A7 B7 Ν- [5- (3-allylhexahydro-2,4,6- Trioxytripyridin-1-yl) -4-mouse-2-aminoepryl] -1-phosphorin-1,2-dipyridinium N- [ 4-Gas-5- (3,5-Diallylhexahydro-2,4,6-trioxy-tripyrazine-butyl) -2-fluorophenyl] -1-cyclohexene-1 , 2-Dicarboxylimide N- {5- (3-allylhexahydro-2,4,6-trioxy-5- (2-propynyl) -color-Sangeng-Buji] -4-chloro-2-fluorophenyl} -1-cyclohexene-1,2-dicarboxylimide, please pay attention to the back of Jing Jing. Animal AI loading page 1 Printed-154 This paper is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) Α7 B7 V. Description of invention (152 ·) · Printed by the Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperatives xsvaz OMVZHl iVSAHO —19 1A13S 8H ° 3 dVIVO SSQdl IvaHoaosvolaiv Η1Π8 &lt; (^ &quot; / 4 / 菜 鹱 々,) 田田 荟 如-「Ϋ 5 Ο Ο Ο c &gt; i ο ο ο ο ο Γ〇cvj ρ ro

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* 1T i'year Printed by Beigongxiao F Cooperative, Central Standard Falcon Bureau, Ministry of Economic Affairs -160- This paper is applicable to the Chinese National Standard (CNS) A4 specification (!! 0X297mm)

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V. Description of the invention (162 · ί · XSV3Z OMVZyi IVSAHOAmMX—lo> i3s 0.0 0.0 00 0.0 0.0 0.0 0.0 00 00 00 00 00 0.0 00 0.0 A7 B7 Please λ Leap to read the meaning of the back! Fill in the page! Quasi-Bureau! Printed by Beigong Consumer Cooperative ΟΟΗΟΙ3 aosvol-I1382IV asi) Π ^ 00 00 00 0.0 0.0 5 0.00.0 0 &gt; 0.0ο.ς0 · ζ 00 ΟΌ 00 00 00 0.0 00 00 00

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Claims (1)

Scope of patent application-a compound YRX with the following structural formula. Printed by the Ministry of Economics and Trade, the Ministry of Economic Affairs and Industry Cooperative Consumer Cooperatives, each of which is hydrogen, halogen, nitro, cyano, alkyl, c "c4haloalkyl ' (Vq alkoxy, Ci_C4 is taken from alkoxy or s (0) mR_2} as an integer of 0, 1 or 2; — alkyl or (^-(: 4 haloalkyl; R is 氲, crc6 alkyl, C2-C12 alkoxyalkyl, C3-Cl # carbonylalkyl, C3-C12 haloalkane carbonylalkyl 'c3-ci2 alkoxycarbonylalkyl, c3-c12_ appearance oxygen kiln group' C3-C6 柽 基, c3 -C6 block group, base metal, phenyl substituted with one to three halogens, Crc4 alkyl, CrC4 alkoxy or ^ -pyridohaloalkoxy as appropriate, or one to three halogens, Ci-q as appropriate Alkyl, Ci-q alkoxy or <: 1-(: 4 haloalkoxy substituted benzyl; Ri is hydrogen, C3-C6 alkenyl, c3-c6 alkynyl, amido, depending on circumstances Or more halogen atoms, or a cyano group, c (o) r3, c (w) r4, oc (o) r5, ch2oc (o) r5, or4, CH2OR4 or cr6 (or7) 2 group or a One to three pixels, CrC4 alkyl, (^-(: 4 alkoxy or CrC4 haloalkoxy substituted 166 This paper size is applicable China National Standards (CNS) Α4 specification (210X 297mm) Please read the back of the matter first. 304158 Ministry of Economic Affairs Central Standards Bureau employee elimination cooperative cooperative printing policy 6, the scope of patent application · phenyl is replaced by (^-( : 12 alkane; i; or optionally substituted with one to three halogens, CrC4 alkyl, q-C4 alkoxyalkoxy substituted phenyl; R3 is OH, 0R8, SR8 or NR9R10; W is 0, NOR9, NCOR9 Or NNHCONH2; R4 'ruler 5 and ruler 6 are each hydrogen' CpC # entertainment * group or C〗 -C4 ^ burned group; ruler 7 is cvc4 alkyl group; R8 is optionally based on crC4 regoxy group 'C ^ -C4 Alkylthio, from the sound, a few groups of 'Crc6 cycloalkyl' furanyl or optionally one or more from the group of 'cyano, nitro, (ν〇4 alkyl, 〇 ^-(: 4 halogen burning group 'CrC: 4 alkoxy or CrC4 haloalkoxy substituted phenyl substituted alkyl; depending on the situation (^-(: 4 alkoxy' halogen, Cg-C: 6 cycloalkyl or depending on the condition C3-C6 alkenyl substituted with one or more halogen, cyano, nitro, Cl-C4 alkyl, CrC4 haloalkyl, crC4 alkoxy 4crc4 haloalkoxy substituted phenyl; as appropriate C3-C6 alkyne substituted by alkoxy or halogen Base: ring appearance base; n = c (r4r5); or metal-examination, earth metal, magnesium copper, zinc, aluminum, silver, nickel, according to, organic ammonium cation; ruler 9 and 111 () are gas, respectively Ci-C ^ alkyl, optionally via one or more halogen, cyano, nitro, Cl-c4 alkyl, C1-C4 haloalkyl, Ci-C4 pitoxy or c ^ -C ^ halo-hyun · Oxygen fetch -167- f, please read the notes on the back first-+ fill in this page j 丨 Ding,,-° The size of this paper is applicable to the Chinese national standard (CNS> A4 specification (210X 297 g; f) Scope of patent application · · A8 B8 CS D8 substitutes for the main group; or optionally one or more halogen, cyano, nitro, Ci-Cj alkyl, cvq haloalkyl, Ci-q alkoxy or cvq halo Alkoxy substituted phenyl; Q is selected from A, • N R 11 \ R12 • R. NN Α, 11A, R, • R, 'NN il \ / NN (please read the notes on the back before filling out this page). Install. 12 Q1 Q2 Q3 VRi1 ~ N people N &quot; -Rii W \ 一 （R12 'R13, R Q4 Q5 Q6 R- 12 and fcN Z, ordered by the Ministry of Economic Affairs Central Standards Bureau employee consumer cooperative printing R 13 rRlx M • N N R 11 R. WRu NN 'R 12 R12 H 12 Q7 Q8 N 0 -N people ^ A, N ix / ~ Z, R12' \ R12 Ql〇Qll 168- Q9 AtRi1 A4 R12 Q12 This paper size is applicable to Chinese national standards ( CNS) A4 specification (210X297mm) A8 B8 C8 D8 6. Scope of patent application Q13 Q14 Q15 Please note the item $ on the back and fill in this page Q19 Q20 Q21 -Λ 〇 人 λ 0 N R12 human Λ — 〇ν r12 甲 I ν ^ Α- R c R 15, 15, Q22 Q23 Q24 • 169- this The paper scale is applicable to China National Standard Falcon (CNS) Α4 specification (210X297mm) 8 3-* 1 4 ΰ 3 ABCD 6. Patent application scope 〇R 16 R 16 R 〇0 R. 1 2 Q25 14 Ν IR · Q26 13 R 13 Q27 〇Μ Ν 13, 14 Ν I R. 11 16 ZO &amp; please read ik's notes before writing this page 13 Q28 Q29 Q30 Q31 Q32 Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Ru and each of which is nitrogen, optionally substituted with one or more halogen atoms, or optionally substituted with one or more halogen atoms c3-c6 cycloalkyl , And when Ru and R12 are bonded together with the atoms to which they are attached, it may represent 4- to 4-inserted with 0, S (〇h or N and optionally substituted with one to three methyl groups or one or more southern atoms) 7-member saturated or unsaturated ring 170 This paper wave scale is applicable to the Chinese National Standard (CNS) Α ·) specifications (210 X 297 mm). In the application of Wai Fanli, ABCD r13, r14 and r15 are each hydrogen, cvqk or CrG haloalkyl R16 is wind or pixel; Rj7 is C1-C4 alkyl or C1-C4 alkyl group; A, A !, A2, A3 and A4 are 0 or S respectively; L is hydroxyl, halogen, CrC3 alkyl Oxygen or (^-<33 alkylthio; M is halogen or CVC3 alkyl; Z is N or CH; Z1 is NR9 or 〇; Z2 is 0R7 or NR9R10; r is an integer of 0, 1 or 2; and q is an integer of 2, 3, or 4. 2. The compound according to item 1 of the patent application scope, wherein X is F or C1; Y is C1; 無 is 〇ν (: 4 alkyl 'Rg is Ci-C4 burning group Q for Xi Group or propargyl and please first read back 'έ matter of note, items fill this page stapling Ministry of Economic Affairs Bureau of Standards staff printed consumer cooperatives Or S (0) -N sV ^ γ ~ 〇3. The compound according to item 2 of the patent application scope is 3- {2-Gas-4-Fluoro-5. -171-This paper scale applies the Chinese National Standard (CNS ) Α4 specification (210 X 297 mm) ABCD ύ ^ 4ϊ〇8, the scope of patent application &quot; · (5,6, Ma, tetrahydro-1,3 · dioxy- 汨 -imi, saliva [5, 1c] [1,4] 4b well. 2_-yl] phenyl} tetrahydro_5_methyl_2,4 &gt; trioxy t Sanwei Xiaoqiu isopropyl acetate® 4.-Species to control unwanted plant species The method includes applying a herbicidal effective amount of a compound of the following structural formula to the leaves of the plant or to the soil or water containing its seeds or other propagating organisms. Please read the precautions R Y 4 Write this page Printed by the Employees ’Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs where X, Y, R, R !, A, A !, 8 2 and Q are as described in item; According to the method of claim 4, the compound is selected from the group consisting of: 3- {2-Gas-4-fluoro-5- [5,6,8,83-tetrahydro-1,3- Dioxo-111-imidazolium [5,1-c] [l, 4] Geng-2 (3H) -yl] phenyl} tetrahydro_5_ 曱 yl_2,4,6-trioxy- Slack-Mitsui-1 (2H) -isopropyl acetate; 3- [2-gas-5- (1-cyclohexene-1,2-dicarboxyimidimide) -4-fluorophenyl] tetrahydro _ 5-Methyl-2,4,6-trioxy-Zantri 4-1 (2Η) -acetic acid tert-butyl ester; 3- [2-gas-5- (1-cyclohexene-1,2 -Dicarboxyamido) -4-fluorophenyl] tetrahydro_5-methyl-2,4,6-trioxy-chromo-sangen-1 (2H) -isopropyl acetate; 3- [2-chloro-5- (1-cyclohexene-1,2-dicarboxyimidimide) · 4 · fluorophenyl] tetrahydro-5-methyl-2,4,6-trioxy- Shiba-San-Jing-1 (211) -Methyl Acetate; -172 The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (2! 〇X297 public meeting) Α8 Β8 C8 D8 Patent scope 3- {2-gas -4-Fluoro-5-[(Tetrahydro_3 oxy'neura,] Chongdiazolidine [3,4-a] aza-1-ylidene) amino] phenyl} Tetrahydro_5 _Methyl-2 4,6_trioxy-blue-di 11 well-1 (2Η) -isopropyl acetate, and 3- [2_gas-4-fluoro-5- (tetrahydrodecane 3, 7. Three oxygen基 -m_ 咪 闻 幷 [5, ㈣ρ 4] .Hei H) -yl) phenyl J tetraki_5_methyl_2,4,6_trioxytridecyl ^ -1 (2H)- Isopropyl acetate. One == Rifan Gudi's method, in which the compound is applied to the plant in an amount of about 5 winter MA to 4.0 kg / ha, on the leaves of the plant = soil or water containing its seeds or other breeding organic Zhao. — A herbicidal composition, including an inert amount of the following chemical formula carrier and herbicide effective-~ ^ Pack I (please read the precautions on the back ^ fill in this page -in κι · m 1?, 、 一 &quot; &amp; where .Rl A, Aι, A2 and Q are as described in item. -A compound with the following structure. The scope of the patent application, the economy. The Central Committee of the Central Bureau of Labor and Consumer Cooperation. Printed by the company Y 2 This paper wave scale is applicable to China National Xin-173 (CNS) Α4 specification (21〇X Μ7mm) 8 5 4. U 3 ABCD patent application scope.. Where 'T is NH2, -NCO, -NCS, -N3, -NHNH2, -NHC (S) NHRU, -C (0) NHNHR13 »-C (0) H» -C (0) CH3 »-C (0) C02 (CrC4 burned group), -C (0 ) CH2C (0) Ru, -C (0) CH2C (A3) 0 (CrC4 alkyl), -C02 (CrC4 alkyl), -N = C = NRU, -NHC (0) NHRu, -nhc (s) nruhnr12, -n = c (sch3) nhru, -nhc〇2- (CVC4 alkyl), -C (C1) = N0H, please read the precautions R 11 〇N 丫 0 ί 0 Η Ν \ 〇h〇2c &lt; n The Ministry of Economic Affairs, Central Bureau of Standards and Labor ’s Consumer Cooperatives printed X and Y as hydrogen, halogen, nitro, cyano, Ci-q alkyl, Cr c4 haloalkyl, CVC4 alkoxy, crc4 haloalkoxy or S (0) mR2 »m is an integer of 0, 1, or 2; alkyl or CrC4 haloalkyl; R is hydrogen, CrC6 alkyl, c2-c12 alkoxyalkyl, (: 3-(: 12alkylcarbonyl Group, C3-C12 haloalkylcarbonylalkyl 'c3-c12 alkoxycarbonylalkyl, (: 3-(: 12 haloalkoxycarbonylalkyl, c3-c6 alkenyl, c3-c6 alkynyl, depending on the circumstances Three halogens, Crc4 alkyl groups, Ci-q alkoxy groups 174 The paper standard uses the Chinese National Standard Falcon (CNS) A4 specifications (210X 297 mm) 304138 Bismuth C8 ___ D8 6. Apply for a patent Fan Garden · or ci, benzyl substituted with C4 haloalkoxy, or benzyl optionally substituted with one to three halogens, Cl-c4 alkyl, Ci-q alkoxy or C1-C4 haloalkoxy; Rjl is hydrogen 'C3-C6 alkenyl, c3-C6 alkynyl, cyano, optionally via one or more functional atoms, or a cyano group, C (〇) R3, 〇c (〇) R5, ch2oc (o) r5, or4, CH2〇RACR6 (〇R7) 2 group or one to three halogens, Cl-c4 , C 〖-Ci2 alkyl substituted by C1-C4 alkoxy or C "C4 halooxy substituted benzene-yl; or optionally one to three halogens, Crc4 alkyl, Ci-C # alkoxy or CrC4 haloalkoxy substituted phenyl; R3 is or8, sr8 * nr9r10, · R4, ruler 5 and 116 are hydrogen, crc4 alkyl or c "c4 # alkyl; C1-C4 total; Rg is Depending on the situation, through 0-(^ 4 burnt milk group 'Ci-C ^ fe thio group, from the element, light group, c3-c6 cycloalkyl, furanyl group or depending on the situation through one or more dentin' amino, nitrate Group, (^ -04 gauge * group, C ^ -Ca haloalkyl group, C "C # alkoxy group or C 〖-C4 halooxy group substituted phenyl substituted C i-Cg anti-group; as required by εΓ (: 4 alkoxy, -halogen, c3-c6 cycloalkyl or optionally one or more halogen, cyano, nitro, C ^ -Cq alkyl 'cvc4 haloalkyl, (ν &lt;: 4 alkyl C3-c6 alkenyl substituted by oxyhaloalkoxy substituted phenyl; c3-c6 alkynyl substituted by crc4 alkoxy or halogen as appropriate; or ______-175 -____ Called Yunge (2lQx 297 Gongqing) '&quot; (Please read the precautions on the back first and fill in this &quot; Ministry of Economic Affairs ABCD 7 printed by the Central Bureau of Standards 'Staff Consumer Cooperatives, the scope of patent applications ·'. 3_ (: 6 cycloalkyl; R9 and R10 are each hydrogen, Cl-c6 ^ group, depending on the situation one or more halogen, Cyano, nitro, Cl_c4 alkyl, crC4 benzyl substituted by alkyl, Ci-C4 alkoxy or Ci_c4 haloalkoxy; or optionally substituted by one or more nansu, cyano, nitro, Cl_c4 Alkyl, q-C4 haloalkyl, crC4 alkoxy or Ci_c4 haloalkoxy substituted phenyl;, Ru &amp; r12 are each hydrogen, and Cl-C6 alkanes substituted with one or more halogen atoms are optionally washed Group, or a C3-C6 cycloalkyl group substituted with one or more halogen atoms as the case may be, and when 11 and 12 are combined with the atoms to which they are attached 8Φ _-, may represent 0, S ( 0) r4 N and 4- to 7-membered saturated or ^ substituted by -5-V two or even one or more halogen atoms, as appropriate. A run and ring R13 is hydrogen, C!-C 3 burned group or C i-C 3 halo group; A, Aι, eight 2 and eight 3 are respectively 0 or S; and r is an integer of 0, 1 or 2. Printed by the Beigong Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the note 14 on the back to write this page) 9.—A compound with the following structure ^ 04158 A8 B8 C8 D8-The Ministry of Economy ’s Central Bureau of Samples and Printing, the scope of patent application, and the scope of patent application.. Among them &gt; 1'1 is 1 ^ 02, 1 ^ 152 or-&gt; 711 (:( eight ) 1 ^ 1111; A, 8 3 and 8 4 are each 0 or S; X and Y are each hydrogen, halogen, nitro, cyano, cvq alkyl, cr &lt;: 4 haloalkyl, CrC4 alkane Oxygen, CrC4 South alkoxy or S (0) mR2 fm is an integer of 〇, 1 or 2; alkyl or (^-(: 4 haloalkyl;-R is a rat 'Ci-Cg kneel group' C2- C12 pit milk burning group, C ^ · _C12 Hyun • Betrayal group, C3-C12 halogenated alkyl carbonyl alkyl group, C3-C12 alkoxy carbonyl alkyl group, (: 3-(: 12haloalkoxycarbonyl alkyl group, c3- C6 alkenyl, _c3-c6 alkynyl, optionally substituted with one to three halogens, 0 ^-(^ 4 alkyl, Ci-C4 alkoxyhaloalkoxy substituted phenyl, or optionally one to three halogens , Ci-q alkyl, crc4 alkoxy or (^-(: 4 haloalkoxy substituted benzyl; each is hydrogen, as appropriate, crc6 alkyl substituted by one or more halogen atoms, or as appropriate C3-C6 cycloalkyl substituted by one or more halogen atoms, and when ^^ and! ^ 2 are combined with the atoms to which they are attached, it means that there are Ο, S (0) r4 N and optionally a 4- to 7-membered saturated or unsaturated ring substituted with one to three methyl groups-or more tooth atoms. And Γ is an integer of 〇, 1 or 2 10. Methods for preparing compounds with the following structural formula 177- (please read the precautions on the back and fill in this page first), 1T training paper size applicable towel _ home standard (CNS) Μ specification (210X297 mm) A8 B8 C8 D8 6. Scope of patent application ^ · S Wherein X and Y are each hydrogen, halogen, nitro, cyano, Crc4 alkyl, CV c4 haloalkyl, CrC4 alkoxy 'crc4 haloalkoxy or S (0) mR2 I m is 0, 1 or Integer of 2; R〗 is a kneeling group or a C1-C4 tooth group; R is hydrogen, CrQ alkyl, C2-C12 alkoxyalkyl, (: 3-(: 12alkylcarbonylalkyl 'C3-C 12 Draw burn a few rules 1 group 'C3 C12 burned oxygen cutting pit group' C3_Ci2 draw oxycarbonyl alkyl 'C3-C6 dilute group, C3-C6 alkynyl group, 絵 · metal, depending on the situation through one to three halogen, cvq alkyl group , Cvq alkoxyhaloalkoxy substituted phenyl, or optionally benzyl substituted with one to three halogens, Crq alkyl, Ci-C ^ alkoxy or (^-(^ haloalkoxy; economic Printed by the Consumer Labor Cooperative of the Central Bureau of Standards of the Ministry of Education (please read the note 1 on the back to fill in this file) Ri is hydrogen, C3-C6 alkenyl, C3-C6 block, cyano, depending on the situation. Atom, or one cyano group, c (o) n3, oc (o) r5, ch2oc (o) r5, or4, CH2OR4 or CR6 (OR7) 2 group or one to three halogens, optionally Ci-Cj alkyl , Cj-C; Ci_Ci2 calcined by 4 alkoxy or oxo ^ halo entertainment> oxy substituted phenyl ; Or ____ -178- Chinese standard (CNS) M specifications (2lQX 297 male) ABCD 304158 is applied to the most daring scale. Six, patent application scope.. · One to three halogens, Ci_, c4 alkyl, Ci_c4 as appropriate Alkoxy or C1-C4_alkoxy substituted phenyl; R3 is 〇R8, SR8 or NR9R1〇; r4, r5 &amp; r6 are each argon, Ci-c4 alkyl or ^-cardiac alkyl; 7 is crc4 alkyl; Rs is optionally Crc4 alkoxy, Crc4 alkylthio, halogen, hydroxy 'C; 3-C6 cycloalkyl, furyl or optionally one or more halogen, cyano, nitrate Group, Cl_C4 alkyl group, Cjrc4 ^ alkyl group, CrC4 alkyloxy group or Cl_c4 haloalkoxy substituted phenyl substituted Ci_C6 play group; optionally via Ci-q alkoxy group, i element, C3-C6 cycloalkyl group Or optionally substituted by one or more phenyl groups substituted by element, cyano, nitro, Cl-c4 alkyl, crC4 alkyl, 〇1_〇4 alkoxy or crc4 alkyloxy C3-C6 alkenyl; c3_c6 block group substituted with alkoxy or halogen as appropriate; or <:: 3-(: 6cycloalkyl; ruler 9 and ruler 10 are each hydrogen, (^ -(^ Burning base, according to one or Halogen, cyano, nitro, Ci_c4 alkyl, CrC4 southern alkyl, CrC: 4 alkoxy or Ci_C4 haloalkoxy substituted benzyl printed by the Employees ’Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs; or — as appropriate Phenyl substituted by one or more halogen, cyano, nitro, C1_C4 alkyl, Ci-C4 haloalkyl, CrC4 alkoxy or Cl-C4 haloalkoxy; Ru and R12 are each hydrogen, __ 二 179- The standard of Tsukaji is applicable to China National Standard (CNS) A4 specification (ΪΤ ^ 297mm). 304158 ABCD Patent application range _ · Cl_C6 alkyl substituted by one or more South Plains as appropriate, or C3-C6 cycloalkyl substituted with one or more halogen atoms as the case may be, and when combined with the atoms to which it is attached, it may represent that 〇, S (〇) piN is optionally inserted and optionally-through three A methyl group or one to more than one _ atom substituted anal to, abalone and or unsaturated ring A 'Αι' A2 'eight 3 and A4 are respectively 0 or s; and r is an integer of 0, 1 or 2; the The method includes making the amine R of the following structural formula Y Please read the notes on the back first! Ψ., Write this page) 7 where X, Y, R, A, eight! A2 The acid anhydride compound as described above reacts in the presence of an acid with the following structural formula-Order R. Λ Μ The Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperative Printed Ru, Rl2, Ba 3 and Ba 4 as described above The compound forms the following structure R X ^ Ύ -180- The paper size is applicable to China National Standard (CNS) Α4 specification (210Χ 297mm) Printed and printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, where X'Y, r, Mi'A'A), A2, A3, and A4 are as described above; and the alkylating agent of the following structural formula is used in the presence of alkali as appropriate Where R1 is hydrogen, the desired compound is alkylated RiXi, where Ri is C3-c6 octyl, C3-C6 alkynyl ', optionally one or more _ atoms, or a cyano group, c (o) r3' 0C (0 ) R5, CH20C (0) R5 ^ 0R4 »CH2OR44GR6 (OR7) 2 or one optionally through one to three halogen 'Ci-C4 entertainment * group' cv c4 alkoxy or (: 1-0: 4 haloalkoxy CrCu alkyl substituted by substituted phenyl, or phenyl substituted with one to three halogens, CVC4 alkyl, CrC4 pitoxy or CrC4_alkoxy as appropriate; and Xl is Cl, Br or I. -181 -