JPS5823674A - Herbicidal diazole and triazole ureas - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention]

The present invention relates to diazole and triazole ureas and agricultural
chemical substances and their use in particular as herbicides.
It is something that U.S. Pat. No. 4,127,405 states that formulas R3 and R6 are independently hydrogen, fluorine, chlorine, bromine, iodine.
element, alkyl having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms
Koxy, nitro, trifluoromethyl, cyanide, CH3
S (0) - or CH, CH, S (0) -,
R4 is hydrogen, fluorine, chlorine, bromine or methyl; R5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy
Yes, R1 is hydrogen, fluorine, chlorine, bromine, or an alkali having 1 to 2 carbon atoms.
Cyl or alkoxy having 1 to 2 carbon atoms, R8 is hydrogen, methyl, chlorine or bromine, Ro and R
1° is independently hydrogen, methyl, chlorine or bromine; W and Q are independently oxygen or sulfur; n is 0.1 or
is 2, xu water-i, m, bromine, methyl, ethyl, carbon number is 1
~3 alkoxy, trifluorome-fk, CH3S-
or cH, OCH, -, and Y is methyl or methoxy, provided that (a) when Ra is other than hydrogen, R9, R,
, R, and R2 must be other than hydrogen, and at least two of R, R, R6 and R2 must be hydrogen; (b) R is hydrogen and R8, R ,, R6 and
and R7 are all other than hydrogen, then all of R3, R4, R6 and R7 must be chlorine or methyl, and fc) When both Rs and R9 are hydrogen,
At least one of R4, R1+ or R6 must be hydrogen
Compounds or compounds useful for controlling weeds in wheat that have
teaches salt suitable for agricultural use. French patent 1.468.747 is applicable as an anti-diabetic agent.
The following para-substituted phenylsulfonamides
discloses: [wherein R is H1 halogen, CF, or alkyl]
]. Chem, A by Logemann et al.
b, 53°18052f (1959) is uracil-induced
and [wherein R is butyl, phenyl or R. R1 is hydrogen or methyl.
Disclosed. Test on hypoglycemic effect in mice
(oral dose of 251g9/100t)
), the compounds in which R is butyl and phenyl are the most important.
there were. others were less important or inactive
. Wojc iechowsk
i) Author J, Acta, Po1on, Pharm,
19.121-5 (1962 (Chem, Ab, 5
9 1633e) is N-C(2,6-cymethoxypyrimi
din-4-yl)aminocarbonyl]-4-methylben
Describes the synthesis of zenesulfonamide: CH3. Based on similarity to known compounds,
The authors have predicted hypoglycemic activity for the above compounds.
Ta. Dutch Patent 121 issued on September 15, 1966
, 788 describes the preparation and general or selective exclusion of the compounds in the formula
teaches their use as herbal agents:
kill, and R3 and R6 are independently
Can be hydrogen, chlorine or alkyl having 1 to 4 carbon atoms
can〕. Formula compounds and their use as antidiabetic agents J
, I) rug, Res, 6.123 (1974)
reported in: where R is pyridyl. The presence of undesirable plants is essential for useful crops, especially for humans
Agricultural products such as soybeans, barley, and wheat that meet global food needs
It causes considerable damage. recent population explosion and
The production efficiency of these crops is decreasing due to the associated global food shortages.
Improvements in the rate have been required. One way to improve this efficiency
may be of value for eliminating or inhibiting the growth of undesirable plants.
The goal is to prevent or minimize loss of crop parts. Eliminating or inhibiting the growth of undesirable plants (
A wide variety of substances are available that are useful for regulating
Such substances are commonly referred to as herbicides. however
, control weeds or eliminate weeds without substantial damage to useful crops.
More effective herbicides are needed to retard
Ru. The present invention provides novel compounds of formula I, suitable compounds containing them.
agricultural compositions and as pre- and post-emergent herbicides.
Regarding their use: R13 [wherein R8 is H, C, ~C4 alkyl, C1~C4 alkyl]
Lukenyl, C8-C4 alkynyl, S R4, ORs
%CHt ORs, CHz CHt ORs, N (
CHs)*, CFs, CFt CFs, CI'
-NHCHs, N(CH3), ,CH(OCHa
), or R, is C1-C4 alkyl, C8-C4 alke
Nyl, C3-C4 alkynyl, CHt OCHs, CH
mCHtOCHCHlSCH,,CH,CH,SCH
. or C1-C4 alkyl substituted with 1-3 F atoms
is R, dH or CH3, and R4 is C1-C4 alkyl, C3-C4 alkenyl, C
3-C4 alkynyl, cHtcot R,, or CH
(CHs) co, R, and R11 is C, ~C, 7# * pv, C8 ~ c4 alke
Nil, CB ~C47 Lou! 1- = /I/, CH,
Co, R,, CH (CHm) C0tRs or CH, C
F, R6 is C1-C4 alkyl, W is O or S, R1 is H, C1-C4 alkyl, C1-C4 alkoxy
, Fs C(0)NR, 1RB, C1%Br. Not, CFs, CotRo, 5OtNRt. R
11, c(0)SRt. ,5otN(OC'H5IcH
1, C3-C4 alkenyloxy, C8-C4 alkini
substituted with Hs, 0CHI or OCt Hs
C1~C, alkyl or all~5 CI, 8r also
or F atom or b) OCR, or OCt HIl
C8-C,alkoxy substituted with R, %F%CI, Br, CFs%Not,
C1-C, alkyl or C1-C, alkoxy, Ro is C1-C, alkyl, CHt CHt OCHs
, CH2CHt OCHt CHs, CH, CH, CH
,OCH. CH8, C5-C6 alkenyl, C8-C6 alkynyl
or substituted with 1 to 3 CI or F atoms;
C, alkyl, R1゜ and R11Fi independently C
1-C, alkyl, R1, is C1-C, alkyl, CH, CH, ocH3,
CHt CH! CHt OCH* or 1-3 F%
C1-C4 alkyl substituted with CI or Br atom
and R1 is C1-C4 alkyl, allyl, 1-5 F,
C1-C, alkyl substituted with CI or FiBr atom
nVio, 1 or 2, Q is 0 or NCHs, R,, FiH%CH,, OCH[s, F, CI, Br%
NO2, 80, NR. Rh, 5OtN (OCR++)
CH080, R, or 5(0) RIs, and RI
s is H% Cl s B r % CHm , 0CHs
or No, R+ e 11 H% C6-C4 alkyl, C8-C4
Alkoxy, F%CI, B r%CFs, C0tR
to-8O,NR,. RIs, So! N (OCH3
) CHs or S (0) n R,s, Ro, is H,F%CI, Br, CHs or OCH3
, W' is O or S, R18 is H, C1-C4 alkyl, c, -c, alkoxy
C, F %C1% B rz NO2, Cot Rto
sSo, NR,. R11, S Ot N (OCHs
) CHs or S (0) Rlm, and R1゜ is C1%No, CFCO, RO1So! N(
OCH,)CH3, So, NRI. R11, QSOtR
+*, 8 (0) n Rs s or 1 to 5 CIs too
or C1-C3 alkoxy substituted with F atom
, R7゜ is C1-C4 alkyl, CH* CHt OCH
a, CHmCH1C1 or CH, CH=CH,
Rt, IdC, ~CR alkyl or Cs Hy,
However, the condition is that the total carbon number of ill Rlo and RII is less than or equal to Fi4.
+2J The total number of carbon atoms in R and R1 is 6 or less, and 13) When W' is O, R11l is HlC
I, Br% CHI or Co, R,. and 14) W'
is O, lt and R, is H%C+, Br or CH3.
When , Z beam, (@ When R9 is H, R, is H, and
f7) R, and Rlg are both No.
]. The present invention also provides novel compounds of formula a, containing them
suitable agricultural compositions, as well as pre- and post-emergent weed control.
It also concerns their use as agents. R' [wherein R' is H, CH, or C! H! + and R1
' is CH@, CIH! 1%5CH8,0CH8 or 0
CxHs, 1 R, / is CHa, CtHa or OCH, Z
' is R11dc, ~C4 alkyl, C1-C4 alkoxy,
1% C1,3r, No, % CFs, C0tRo,
So, NR,. R11, C(0)NRztR□, 80,
N(OCHs)CHs, QSOtRlt, 5(0)
R1*, C(0)SRI. , CH, CO, R,. , C.H.
(CHs) Coy Rt. , CHt S (0)n
Rt s, CH(CHs) S (0) n Rsl
, C3-C4 alkenyloxy, C1-C4 alkynyl
C substituted with oxy, 0CR8 or 0CtHa
1-C, alkyl, or all to 5 CIs. Br or #71F atom or ) OCH, if
Kuwa OCt H! t'L * C, -C37
Le: 7 chialkyl or FiC, ~C3 alkoxy
, R, is C8-C6 alkyl, CHt CHt OCH
s, CH, CH, OCH, CH3, CH, CH, CH,
OCH. CH,, C, ~C6 alkenyl, C3~C6 al゛''ki
Nyl or Fi substituted with 1 to 3 CI or F atoms
C8-C, alkyl, and RIo and RII are independently
is C2-C, alkyl, and Rlg is C1-C4 alkyl, CB, CH, OCH, C
Ht CHt CHt OCHs or 1 to 3 F, C
C1-C4 alkyl substituted with I or Br atom
, RlS is C1-C4 alkyl or allyl, R,,
HH,CHs,OCH3,F,CI,B",NO,
,5OzNR+oR++,5O2N (OCHm)C
Hs, OS Ot R+ or 5(0)R+a
, R16FiH* C1~C47 Ru # Ru, c1~c4
Arcogysi, F % CIs B r, CF *
, CO2R2゜, 5O2NRso RIr, So! N
(OCH3)CHs or 5(0). R13, RIaViH% C1-C4 alkyl, c1-c4 alco
xi, F% CI, sr, No,, cO, R, o. Box NR+ n RIr -S02 N (QCH
a) CHs or 5(0)R+s, R2o is C, ~C4 alkyl, CH, CH, 0CH1,
CH, CH, CI or CH, CH=CH, and Q is
O or NCR, R2, idc, ~C, -rlkyl or C61-1! I
, Ro is C1-c3 alkyl, and Ro is
However, the condition is that (x) the total number of carbon atoms in Rlo and R11 is 4 or less.
, and (2) R,' and RI cannot be H at the same time.
do not have〕. Relatively high herbicide activity or relatively large preferred synthesis
For reasons of ease, the following are preferred: (1) The formulation of formula ■, where W is O and R8 is H.
compound, (2) Z is W/ is S, R+ o KaCot CHs, 5OtN (CHs
) t is also H3O2CHs and R, 11 and R1 are H, (3) Preferred compounds of 2, where Z is, +41 R, is C1-C, alkyl, SR4 , ORs
, CH, OCH,, N(CH,), or CI, and R
1 is C1-C, alkyl, CH, CF,, CH, CH=
CH, or CH, C=CH, and R4 and RIr are independently CH, or CtHs
Preferred compounds of 3, wherein R1 is other than H and R6 is H, F, CI, Br%CF, , CH3 or O
Preferred compounds of 4 are CHs, f6) R, is C1, Not , C0tRo , 5O
tNRIoR1s, or OS Ot Rt t, H6゛ is H, R, is C1-C3 alkyl, CH, CH=CH,, CH
t CHt OCHs or CH, CH, CI, and R
lo and R11 are independently C1-Ct alkyl,
and Rlf and R1 are independently C1-C3 alkyl
, preferred compounds of 5, (7) Re , Rho, Rtt , Rtt and R13
is CH, Preferred compounds of 6, +81 R' is CH3 or Ct Hs
Compound of Ta, R8 is H%F, CI, B r , CFB , CHs
or 0CHs, (]0) R? is CI, NOt, Cot Ro,
Soy NR+o R11,080, R, or So,
R, , R8 is H, R, is C1-Cs alkyl, CH, CH=CH,, CH
t CHt OCHs or CH, CH, CI, and R
1° and R11 are independently C6-C, alkyl,
and Rlf and R1 are independently C1-C, alkyl
, preferred compound 9, (11) Rg % RHo % Rns R+
and R5, is CH8. their highest herbicide activity and/or greatest preference.
For reasons of ease of synthesis, the following are particularly preferred:
2-[[(5-methylthio-1-methyl-IH-1,2
,4-triazol-3-yl)aminocarbonyl]a
Minosulfonyl]benzoic acid methyl ester, 2-[(5-ethylthio-1-methyl-IH-1,2,
4-1 rian-3-yl)aminocarbonyl]a
Minosulfol]benzoic acid 4-thyl ester, 2-[[(5-ethyl-1-methyl-IH-1°2.4
-) lyazol-3-yl)ami7carbonyl]amine
Sulfonyl]methyl nisder benzoate 1 2-ri5-methoxy-1-methyl-IH-1゜2.4
-) lyazol-3-yl)ami, nocarbonyl]ami
sulfonyl]benzoic acid methyl ester, N-[(5-methoxy-1-methyl-IH-1°2.4
-triazol-3-yl)aminocarbonyl]-2-
Chlorobenzenesulfonamide, N-[(5-methoxy
-1-methyl-IH-1゜2.4-)lyazole-3-
yl)aminocarbonyl]-N',N'-dimethyl-1
, 2-benzenedisulfonamide, 2-[(4,s-dimethyl-1H-imi-zole-2
-yl)aminocarbonyl]aminosulfonyl]benzoin
Acid, methyl ester. Many of the compounds of synthetic formula (■) have the formula as shown in reaction formula 1.
■ An appropriate 3-amino-1,2,4-) lyazole with the formula
(2) Suitably substituted sulfonyl isocyanate or
It can be produced by reacting with antithiocyanate. Reaction formula 1 [wherein Z, R1, R,, R, and W are defined above]
] The reaction of Scheme 1 is best carried out in an inert organic solvent, such as a salt.
(methylene chloride, tetrahydrofuran or acetonate) II
The test is carried out in a chamber at normal pressure and temperature. The addition method is strict.
No, but sulfonylisocyanates or inthiocyanates
nate in a stirred suspension of aminotriazole or
is often convenient to add to the solution, such
Incyanates and inthiocyanates are normally liquids.
Therefore, their addition can be easily adjusted. The reaction is generally exothermic. In some cases, the desired
The product is insoluble in the wet reaction medium and then
Crystallizes in pure form. products that are soluble in the reaction medium
The solvent can be evaporated and the solid residue e.g.
Tritify with a solvent such as ethanol or ethyl ether and filter.
It is isolated by filtration. Another method for synthesizing the compound of formula ■ where W=0 is shown in reaction formula 2.
show. A suitable sulbonyl isocyanate of formula Tn can be expressed as
the appropriate 3-amino-IH-1,2゜4-triazole
to give the intermediate product urea of formula ■, which
is then alkylated using reagents of formula R and X to form formula ■
Forming a compound: Reaction formula 2 [wherein X is a good free radical, such as bromine, iodine, chlorine]
, alkyl sulfonate, Rt OS O'j' or p-) luene sulfonate,
, and Z%R, , R, and Rs are defined above.
] In reaction formula 2, 3-amino-IH-triazo of formula (■)
and sulfonyl isocyanate or sulfonyl inch
The conditions for reacting oceanate are as shown in reaction formula 1.
The conditions listed for the triazole 1Tt-containing condensation and
Similar, but with equimolar amounts of sulfonylisocyanate
It is desirable to react with triazole (■). Sulfonylurea intermediate product V shown in reaction scheme 2
and R,X (where X is a good free radical, e.g. bromine, iodine)
Uron, chlorine, alkyl sulfonate, R, 08030 or
is p-) luenesulfonate,
The reaction is preferably carried out in the presence of an alkaline substance and preferably
is carried out in the presence of a solvent. suitable alkaline substance
For example, alkali and alkaline earth metal carbonates, charcoal
Hydrogen salts, acetic acids and hydroxides, such as potassium carbonate
aluminum, sodium carbonate, potassium carbonate, potassium acetate, water
Contains sodium and potassium oxides. other organic bases
can also be used, such as pyridine and triethylamine.
Ru. Suitable solvents include inert aprotic solvents, e.g.
Acetone, methyl ethyl ketone, acetonitrile, chloride
Methylene, dimethylformamide, dimethylacetamide
and dimethyl sulfoxide. A of reaction formula 2
The alkylation reaction conditions are based on the reactants, base and solvent present.
Varies depending on the nature of the medium. Usually the reaction is heated (45°~1
between 28°), but this technical expertise
If there is such a thing as would be readily apparent at home, then
Lower reaction temperatures are also desirable. Compounds of Formula Ia are prepared by the general process of Scheme 1.
Ru. Z', R', R; and R; are defined in the preceding statement e.
Therefore, W is O. Reaction Scheme 1a Snow III R/Dan LR'-Lee The reaction of Scheme 1a is carried out in an inert aprotic solvent, e.g.
Methylene chloride, tetrahydrofuran or acetonitrile
, at normal pressure and temperature. a certain place
If the desired product crystallizes from the reaction medium and
I can filter it. Reaction products that are soluble in the reaction medium
Evaporate the solvent and remove the residue with e.g. diethyl ether.
, trituration with a solvent such as 1-chlorobutane or hexane
It can be isolated by For purification, chromatography (
eg silica gel) is also required. Intermediate product aryl sulfo-lysocyanate of formula 10
Neni) (W=O) is H. Ulrich (formerly
Written by A, A, Y, Sayigh, New
er Methods of Preparation
iveOrgamic Chemistry, Volume ■,
pp. 223-241, Academic Press, New York.
London, W., Forest E.
d or according to the method of U.S. Pat. No. 4,127,405
(1978), U.S. Patent 4,238,671 (198
0) and as taught in European Patent No. 23.141.
In the presence of n-butyl isocyanate,
For example, in a flowing solvent such as chlorobenzene or xylene.
Reacting the corresponding arylsulfonamide with phosgene
It can be manufactured by The intermediate product pyridylsulfony of formula 1 [(W=O)
Lewis isocyanate is recorded in Euronoha% tolerance 13.480.
N-(alkylaminocarbonyl)pyri
Synthesis is achieved by reacting dinsulfonamide with phosgene.
can be manufactured, the disclosures of which are included here for reference.
put. N-(alkylaminocarbonyl)pyridine sulfate
Honamide is described in U.S. Patent Application No. 966.258.
As shown, pyridine sulfonamide, alkyl group
Reacting nocyanate and anhydrous base in an anhydrous solvent
It can be manufactured by Similarly, the production of French sulfonyl isocyanate is
Patent No. 4.127.405 (noted in 19781)
thiophene and naphthalene sulfonyl isocyanate
were prepared as shown in Reaction Equations 3 and 4, respectively.
You can build it, and here R14, R1! I, R1, and Ro are
1, as defined in Scheme 3. A suitable sulfonamide, e.g.
2-alkoxycarbonyl-3-thio such as esters
Fensulfonamide VI, alkyl isocyanate,
For example, butyl isocyanate and a catalytic amount of 1,4-di
Aza[2,2,2]bicyclooctane (DABCO)
The mixture can be purified using xylene or a sufficiently high boiling point (e.g. >135
℃) in another inert solvent to about 130-150℃.
Ru. Add phosgene to the mixture as indicated by boiling point depression.
Add until excess phosgene is present. mixture
Cool and filter to remove small amounts of insoluble by-products
After that, the solvent and alkyl isocyanate are evaporated in vacuo.
Distillation removal gives a residue, which is the crude sulfonyl isocyanate.
This is Nate ■. ”v7TX Naphthalenesulfonyl isocyanate■ is the corresponding sulfonyl isocyanate
Can be produced from honamide ■. Reaction conditions for phosgenation
are the conditions for thiophene sulfonamide in reaction equation 3 and
It would be the same. Phenylogysis sulfonylinocyanate of formula M is available in the United States.
As taught in Patent No. 4,191,553 and
The corresponding phenol of formula X as shown in reaction scheme 5
It is easily manufactured from High boiling point it[, e.g.
Lobenbin, toluene or haxylene, X and chloro in
The reaction of sulfonylisocyanate is
Manufacture socyanate. Reaction formula 5 Formula m (W=S) - Rusulfonyl isocyanate
Arch by K,/Sk (Hartk6). Pharm, 229.174 (1966)
Treatment of sulfonamide with carbon disulfide and potassium hydroxide
By reacting perilla extracted potassium salt with phosgene,
can be manufactured. Pyridine sulfonyl thiocyanate UK. Dig v (Dickere) and E, Kuh
as taught by U.S. Pat. No. 3,346,590
It can be manufactured according to the following process. suitable pyridine sulfo
Nyliminodithiocarbonate? For example toluene or
React with phosgene in the presence of a solvent such as silene. Thiophene prepared according to Reaction Schemes 6 and 7 and Formula ■
The French sulfonyl inthiocyanate intermediate product of
It is useful for producing the compound of formula (W=S). Reaction formula 6 Substituted sulfonamide containing 1 equivalent of carbon disulfide
Dissolve in dimethylformamide (DMF) and
2 equivalents of potassium hydroxide were added portionwise at room temperature.
. The mixture was stirred for 1-8 hours and diluted with ethyl acetate, ethyl acetate, and ethyl acetate.
diluted with diluted ether or similar aprotic solvent.
Precipitate the ocarbamic acid noncalcium salt. salt
Remove, dry, and remove with an inert solvent, such as
carbon tetrachloride or methylene chloride, suspended in
3. Add phosgene to the stirred suspension at a temperature below room temperature.
and stir the mixture for 1-3 hours. phosgene
zo♀r o, @, $ x, x kotanisuvru) Phosphorus pentachloride
, sulfuryl chloride or thionyl chloride can also be used. The generated sulfonyl inthiocyanate is commonly found in the solvent.
soluble potassium chloride, and insoluble potassium chloride is separated by F.
Then, it is isolated by concentrating the F solution. these
Intiocyanate is unstable and easily difumes
(Reaction formula 7), but the dimer is the object of the present invention.
It can be used in the same way as the original intiocyanate.
Ru. Reaction formula 7 Naphthalene sulfonyl thiocyanate intermediate product order
Also from sulfonamide ■, according to reaction formula 8 and reaction formula
It can be prepared according to reaction conditions similar to those in 6. these
Is intiocyanate also unstable and trimerized?
However, these dimers are also not suitable for the purposes of the present invention.
It can be used in the same way as the inchoffanate. ( Sulfone from ammonium hydroxide and sulfonyl chloride
The preparation of amides is described in the literature, for example Crosley ((::ros
J. Am. Chem. Soc.
Widely reported in 60.2223 (1938)
. Certain sulfonyl chlorides are H, T, Klarke (C1a
rke) et al., Org, 5ynth, Co11.1
vol., 2nd edition, 1941, page 85, carbon tetrachloride.
Best achieved by chlorosulfonation of substituted aromatics in the elementary
Manufactured in Other benzenesulfonyl chlorides are
HoL, Yael and F, Sovinsky
Written by Sowinskil, J, Qrg, Chem
. in HCl according to the teachings of 25.1824 (1960).
A suitable aniline is diazotized with sodium nitrite and its
After the diazonium salt in acetic acid with sulfur dioxide and cuprous chloride
It is best produced by reacting with Aryl sulfonamides are manufactured under a US% license of 4,127.
405 (1978), where R,=H,C,~C4al
Coxi, F, CI%Br%Not % CFS;
-IF - Rotupa Patent Publication No. 7687, where R'r
=C0tRe,C0zNRttRtt,C(01
SR+. ; European Patent 23°] 41 (R?
= SO*NR,. Rt I, 80. N (OC'H
, ) CHl); European Patent 23.422 (R
? = OCFm, 0CHFz, 0CFyCFtH1S
(0). R13, where R13 is a fluorinated alkyl
European Patent 44,209 (Rt =
CHt COt Rto, CH(CHs) COtRt
o, CHt S (0) n R+ s, CH(CHI
)S(0)nR,s); European Patent 44.21
2 (R? = QSO* Rtt, cocoa Q=O or
NCH, ); European Patent Application 44,807 (
R,=C8-C,7/I/kenyloxy, OCH. Or substituted with FiOCt Hs,
koxy, 5(0)nR8s, where R13=allyl);
and European Patent Application 44,808 (R?=1-5
(7) C8~ substituted with CI, Br or F atoms
C, alkoxy). Pyridyl Surpone
The synthesis of amides is described in (), -rMachek, M.
ona-1Sch2.84 (1939); L, -F-
Thunus and C.L., Lap.
Written by ierel Ann, Jarn, 33.663 (1
No. 9751 and European Patent No. 13,480
There is. In reaction formula 9, R1 and R14 are 5(0) Rts
Production of aryl and naphthalene intermediate products
It describes the structure. The thioether of formula Xvb can be found in the literature, e.g.
B.R.N., Prasaa et al., Can, J.
, Chem, 44.1247 (1966).
a suitable 2-aminothiophenol or amino
Can be produced from thionaphthalene and alkyl halides. The production of sulfonamide XVd was carried out by the following method.
It will be done. Reaction formula 9 %Formula % A mixture of concentrated hydrochloric acid and glacial acetic acid of a thioether of formula XVb
Sodium nitrite in water at -5°~θ°
Treat with medium solution. Stir for 10-15 minutes at Oo until completely
After confirming proper diazotization, the solution was heated to 5°C.
Mixing excess sulfur dioxide and a catalytic amount of cuprous chloride in rice acetic acid.
add to things Keep the temperature at θ~5° for ~1 hour and then
Raise the temperature to 20-25° and keep at this temperature for 2-4 hours. child
The solution is then poured into a large excess of ice water. Sulfochloride
filtration or for example with ethyl ether.
or extraction and subsequent dissolution in a solvent such as methylene chloride.
It can be isolated by evaporation of the medium. Amination arranged in step (9b) is sulfonyl chloride
such as ethyl ether or methylene chloride.
Treated with excess anhydrous ammonia at 0-25° in a solvent.
This can be easily done by managing the The product sul
If the honamide is insoluble, it can be filtered and then salted.
can be isolated by washing with water. The product is
If the sulfonamide is soluble in the reaction solution, it is
The precipitated ammonium chloride was separated in a furnace and the molten flag was evaporated.
It can be isolated by The sulfonamide (here A/=aryl) of 2XVC is
Clobenzene as appropriate as shown in reaction scheme 10
Sulfonamide (synthesized by US 4p n 4゜127.40
5). suitable sulfo
2 equivalents of an equimolar mixture of amide and mercaptan
Heating in the presence of a base followed by acidic treatment produces XVC.
to be accomplished. As shown in reaction formula 9, sultenamide XVd
It can be produced by oxidizing Fi, XVc. Reaction formula 10 Moofene sulfonamide of formula XV1e and U XVTb
The synthesis of
It can be done. The sulfonyl chloride of formula XVIa is HID,
Harutora 7 () (Artoug old author, -The Ch
e-mistry of ) (eterocycle
ic Compounds”, 38% Inter
Science Publishers, Inc.
, New York, 1952. these are,
in an inert solvent such as, for example, ether.
Mix with t-butylamine and filter the amine hydrochloride.
, and the corresponding N-t- by evaporating the solvent
It can be converted to butylsulfonamide xvtb.
can. Thiophene and aromatic N-t-butyl sulfone
The amide was converted into n-butyllithium, t-butyllithium,
Thiium diisopropylamide and lithium 2,2,6.
Lithiation using 6-titramethylpiperidide
Law UH, W, Gschwend and
H, R, Rodriguez (Qrg by Rodriguez,
Published by React, 26.1 (1979)
and generally kept under an inert atmosphere
A solution of twice the equimolar amount of base, for example in diethyl ether or
is cooled to -78° in an ethereal solvent such as THF.
and by adding a solution of the compound of formula xvIb.
will be held. The compound of formula XVlc has the reaction formula (llb)
Equimolar amounts of the appropriate disulfide (R
Add +5Slt, warm the mixture to room temperature and acidify the mixture.
prepared by washing with saline and evaporating the solvent.
Can be built. Reaction formula 11 (%Formula% () (() On the other hand, as shown in reaction formula (llc), formula XV
To prepare a compound of Id, a lithiated mixture
is treated with equimolar amounts of sulfur dioxide and the mixture is warmed to room temperature.
, filter the solid precipitate and dissolve this salt in engineered ethanol.
and adding an equimolar amount of the appropriate alkyl iodide.
I can do it. This alkylation step is carried out at temperatures between 25 and 78°.
Can be implemented. The cooled reaction mixture was diluted with dilute aqueous hydrochloric acid to give the product.
XVId can be precipitated. Formulas XVIC and X
t-butylsulfonamide of Vld at least equal to
Heating in methanol containing a molar amount of hydrochloric acid
After concentrating the reaction mixture and precipitating the product with ether.
By setting, the formulas XVle and XVTf are respectively
It can be converted into a compound. Another method for preparing thiophene sulfonamide of formula XVIf is described below.
It is written in Equation 12. Reaction formula 12 (12) (12) (12) [Here, X=CI or Br, and R1° and R
o is as defined above]. The reaction of reaction formula (12a) is carried out using an equimolar amount of sodium, for example.
Contains strong bases such as methoxide or sodium hydride
in a polar solvent such as dimethylformamide.
An equimolar amount of a suitable halide xv+y is mixed with an equimolar amount of a suitable halide
mixed with lumercaptan and at a temperature between 50 and 120°
Heating and the product isolated by precipitation with ice water and
This is done by washing with xane. formula xvth
As shown in reaction formula (12b), the compound of
, R,'F, Langler (Langler, Can
, J. Chem, 54.498 (1976).
contact with at least 43 equivalents of chlorine in acetic acid.
It is converted to sulfonyl chloride XVIi. Sulfonyl chloride is prepared by adding ice water to the chlorination mixture.
It is possible to precipitate more. thiophene sulfonyl
Ammonolysis uXVlf of loride is given. a formula in which R1 and R1 are as defined above
The compound Xb (reaction formula 13) is, for example, dichloromethane
twice equimolar amounts diluted in an inert solvent such as
Chlorosulfonic acid 1-temperature odor between 30° and 25°
and the appropriate 3-thenyl sulfide and the mixture was washed with ice water.
and then evaporating the solvent. this
prepared a suitable compound of formula XVIIc by treatment with ammonia.
It can be converted into a chemical compound. The sulfide of formula x[lC is of formula 'XV
It can be oxidized to the compound 11d. Reaction formula 13 (13% formula % (13b) XVBC (13c) In addition, the method described in reaction formula 11 is
It can also be applied to the production of compounds. According to the method outlined in Reaction Scheme 14, RI: becomes H
1 chlorine or bromine, X is chlorine or bromine, and
Formula XVllf, where R1, is as defined above
and xvIh can be produced. Starting from sulfonyl chloride of formula XVIa, di
Low-compounds can be prepared in alcoholic or hydroalcoholic solutions.
2 equivalents of 5tin sodium ammonium at 25-78°
contact with rubber gum and then the formula is RI = CI or Br
By acidifying the products of X■e and XVIIg
, can be partially dehalogenated. 2-halo and 5-halo
Isomers can be separated by column chromatography. A fully dehalogenated compound with R1'7=H is
, use sodium amalgam with a consumption of 3 or more in the reaction
It can be manufactured by These compounds are X as described above.
VIlf and XVI! lh K conversion tale. Reaction formula 14 (14) (14 (14) (14) (14) (14) Required nathiophene sulfonyl chloride and sulfonate
Precursors to mido include substituent CD chemistry and thiophene
Various types depending on its position on the ring (manufactured by D synthesis method)
be done. Direct sulfonation to sulfonic acids or sulfonyl chloride derivatives
The conversion or chlorosulfonation is:)1. D. Hartoughl 7 (%-Th1oph by Hartoughl)
eneand its Derivatives”,
Interscience, New York, 1952.
It can be carried out according to the literature used. 3-alkylti
The structure of the sulfonated product of ophene is reported to be unidentified.
It has been tell. Nuclear magnetic resonance studies show that chlorosulfonation
What happens primarily in the 2-position rather than the 5-position
It shows. Sulfonic acids are prepared using methods well known in the art.
, such as phosphorus pentachloride, phosphorus oxychloride or thionyl chloride
It is easily converted to sulfonyl chloride by chlorinating agents such as
It will be done. Mixing of sulfuryl chloride in dimethylformamide
The thing is written by E, Testa ('l'esta) et al., He1v,
Chim, Acta, 47.766 (1963)
The active thiophene intermediate product thiophene according to the method of
It can also be used to produce sulfonyl chloride. Other intermediate products can be produced by lithiation reactions. child
The chemical research of Gschwind Hl.
and Rodriguezl, H.R., Organic Reactions, Joan.
Willy & Sons Inc.
Published in New York, 1979. of this chemistry
, application to the production of intermediate products used here
An example is shown in the reaction scheme below. Reaction Equation 15 shows the reaction via a lithiated intermediate.
Indicates the production of rufamilthiophene sulfonamide.
Ru. Reaction formula 15% formula% As shown in reaction formula 15, 3-bromothiophene
at -78°, such as tetrahydrofuran.
Converted to 3-lithiothiophene in an inert solvent and
The mixture is then contacted with sulfur dioxide. Generate or
Osulfinate in acetic acid or 2-propanol water at room temperature.
3- by stirring in solution with N-chlorosuccinimide.
Produces thiophenesulfonyl chloride ■Xb. child
The product of is then amine HNR. R1, (here R1゜
and 81 - and R1, are as defined above).
let 3-thiophene sulfonate produced in this way
Amide ■Xc f With butyl lithium at -40~0℃
, and then reacted with sulfur dioxide to form lithium tertiary-sulfamide.
Generate Ru2-thiophenesulfine-HXXd,
It is converted to the sulfonyl chloride as in Hp above. this salt
Sulfonamide and sulfonyl isocyanate of sulfonyl
Conversion to nate is carried out as described above. Synthesis of other intermediate products via lithiation]
6, where R1, optionally C1, Br, C1-C
4 alkyl, C3 alkenyl or OCH. Equation 16 %Equation % The reaction described in Equation 16 has been described by experts in the art.
What is written in Reaction Formula 15 as shown on the Riko side
is carried out in the same way. Activation from thiophene nucleus
Substitution and production of rogene atom with benzyl mercaptan
The chlorination of the product is also shown by reaction equation 17.
The compound of the present invention may be useful as an intermediate product for Jppq.
It is a process. Reaction equation 17 Teal field where halo atoms are sensitive to substitution by nucleophilic substances
There is no reaction between benzyl mercaptan and haloquinafen.
Active polar high-boiling solvents such as dimethylformamide
or N-methylpyrrolidone in the presence of a copper catalyst under reflux.
It is best carried out for 6 to 48 hours under normal conditions. Thio
Ether intermediate XX'lb can be obtained by converting chlorine gas to hydrochloric acid.
or by passing it through an aqueous acetic acid solution or a suspension of XXIb.
and is converted to sulfonyl chloride XXIC. Henriksenl and Autoluis
(Autruys+, Acta, Chem, 5c
ands, 24.2629 (reported by 19701
Binarized products such as the structural formula XXfi・reaction formula 18
Useful for conversion to sulfonyl chlorides as shown in
It is an intermediate product. Reaction formula 18% Formula% Reaction formula] Chlorination shown in 8 is a salt of structural formula XYlb.
It is carried out in the same manner as arranged for priming. 10,000, of the thio7ene amine shown in reaction formula 19
For example, diazo to sulfonyl chloride such as structural formula XXIV.
The reaction is H, L, Jarl and F. Sowinsky, J. Org, Chem, 25
．． 1824 (carried out according to the general method of 19601)
Ru. Reaction formula 19 % formula % is one (IJ Amson) according to reaction formula 20a or 20b.
Reaction formula 20a XXVa XXVb Reaction formula
20b R'=C, ~C! Alkyl. “Williamson Synthesis” is by W, Teilheimer (The
Written by Syn, Meth
ods of Org. Chem, volume ■, p. 112.
It is widely used for the production of esters. On the other hand, 0-alkoxymethylmethylbenzenesulfonyl
Chloride XXVf is shown in reaction formulas 20C and 20d.
Suitably substituted α-hydroxy-〇-
Toluenesulfonic acid-α-sultone XXVd to alco
Obtained by an open reaction using oxide anions. Reaction formula 20c Reaction formula 20d 8 XVf Reaction formula 20c is based on J, H.
erl et al., A.S., Tatemi Σ, 22 (opened in 19491).
Alkoxides and alkoxides using sultones as shown
Very relevant to cetamide alkylation. Then
Conversion of sulfonic acid to sulfonyl chloride is performed by Org, 5ynt
to the teachings of hesis C011, volume IV 846.693
It will be done accordingly. Benzene sulfonamide of formula XXVIb can be synthesized by reaction formula 2
As shown in 1, it is also induced from compound XXVla.
I can guide you. Reaction formula 21 % formula %] O-alkoxyethylbenzenesulfate of formula xxVnb
Honamide has the formula X as shown in Reaction Scheme 22.
XV [la suitable benzenesulfonyl chloride
It can be produced by a lithiation chemical method. This type of reaction is well known in the literature and
By End, H.W., and Rodrigues H6R0, 10r.
ganic Reactions, Volume 26, Joan
・Willi & Sons Inc.
New York, was attacked during 197Q. Reaction formula 22 % formula % 〇-Sulfa from saccharin or sulfobenzoic anhydride
The production of milbenzoic acid ester is well known in rock technology.
Ru. For example, B, Loev and M, -tlumen.
Day (Kormendyl, J. Org. Chem, 27.1703 (19621° Ester is
, R.P., Graber and M.B., May.
Meyers, J. Org, Chem
, 26.4773 (as noted in 19611
, in a suitable organic solvent such as, for example, tetrahydrofuran.
A 15-fold excess of trifluoride is refluxed in the presence of boron etherate.
Easily synthesized using diborane for 18 hours under
You can get A by turning it into ether. Most commonly, naphthalene sulfonamides are
G, Hilgetag and A, Mal
Martini, -Preparativ
e Organic Chemistry”, J.
During Lee & Sons, New York (1972)
It can be prepared from sulfonyl chloride as noted. salt
Sulfonyl chloride is used for chlorination of sulfonic acid XXVlla.
Those described by Hilgetag and Multi-2 quoted above.
It can be manufactured by the method. The production of these acids is not well documented in the art.
It is. These compounds are prepared by methods known in the tub technology.
Further conversion to produce other disclosed sulfonic acids
do. Reaction formula 23 The desired sulfamylnaphthalene sulfonamide is
similar to that taught in Roppa Patent No. 23,141.
It can be manufactured by a method. The benzyl sulfonamide of formula XXIXd is shown in Reaction Scheme 24.
It is most easily produced as shown in . Formula XX
Bromination of appropriately substituted toluene derivatives of IXa
and then reacted with thiourea to form the formula X\lX b
gives the thiouronium salt of Salination of formula XXIXc
Production of sulfonyl is accomplished by oxidation/chlorination of XXIXb.
Easy to carry out [Production of thiouronium salts and oxidizing salts]
T, 8°Johnson (Johnsonl)
and J.M., Spraguel, J.A.
m, Chem, Soc, 5811348 (193
6); Id. 59.1837.2439 (19371; Id.
See supra, 61, 176 (1939)]. XXIX CI
:) 7 Mi/ is a sulfonamide of formula XXIX d
give. , /″″″ Reaction formula 24 % formula % - 10,000, formula XX]Xe benzyl chloride is in reaction formula 25
Benzyl sulfone of formula XXIXd as shown
Can be converted to amide. Reaction formula 25 XXIX d is phosgenated to form the corresponding formula XXIX f.
The reaction method for benzylsulfonyl isocyanate
It proceeds easily (completely) as shown in Equation 26.
See Reaction Scheme 3 for details). Reaction formula 26 The production of 3-amino-1,2,4-) riazole is based on the state of the art.
and 1,2,4-triazole is T
he Chemistry of Hetero-cy
clic Compounds ” 'priazol
es 1 +2+4” (Joan Willey &
Sands New York, 1981). A commonly used nitrogen-containing starting material is N-aminogua
Nidine, hydrazine, alkylhydrazine, cyanamide
, ethylcyanoacetimidate, dimethylcyanoditidate
Oimido carbonate, dimethylcyanoimide carbonate
Toximethylene cyanamide and acylhydra
It's gin. Some literature synthesis methods are shown below. This technique
These techniques or suitable modifications may be obvious to technical experts.
3-amino-1,2,4-triazo
intermediate products can be easily produced. Equimolar amounts of ethylpropionimidate salt in pyridine
When the acid salt and N-aminoguanidine nitrate are heated, 3
-Gives amino-5-ethyltriazole; German special
1,073.499 (1960); Berich
te, 96.1064 (19631°hydrazine and
Condensation Fi3-amide of ethyl N-cyanoacetimidate
gives no 5-methyltriazole; Journa
l of Qrganic Chemistry. 28.1816 (19631゜trifluoromethyl 3-aminotriazole is trifluoromethyl 3-aminotriazole
Obtained by thermal dehydration of hydrazide of oroacetic acid. Zh,
0bshch, Khim, 39.2525f1969)
;Chemical Abstracts, 72:
78954 v (19701゜Mono patent 2,835,581 (1958)
3-amino-5 from no-guanidine and glycolic acid
-Disclose the production of (hydroxymethyl)triazole
and British Patent 736.568 (1955) 3
-Describes the synthesis of amino-5-mercapto-triazole
ing. Hydrazine and dimethylcyanodithio in acetonitrile
The condensation of imidocarbonate is 3-amino-5-methylthi
o-1,2,4-) lyazole, but hydrazine
The reaction between and dimethyl N-cyanoimidocarbonate is 3-
Produces amino-5-methoxy-1,2,4-) lyazole
Journal of Organic C
hemistry, 39.1522 (1974
). Substituted hydrazine and N-cyano-thioimide carb
Written by Nate (D, M, Wie-1 and)
, Ph.D., Thesis, 1971.123~
(produced according to the process shown on page 124)
produces a disubstituted amino) IJ azole as shown below.
to be accomplished. The aminoimidazole of the formula [a and the method for producing them are
Techniques well known [e.g. J. Org, Chem, 29.3118 (1964); L
iebigs Ann, Chem, 1602 (197
9) ]. What about the general announcement, Hof? 7 (by Hoffmannl,
” lm1dazole and its Der
ivotives”, New York, Interscient.
Pozharshiil, 1953;
Garnoskii ((+arnonskiil and Simono 7
(Simonov), Ru5s, Chem, Rev,
35.122 (19661; Elder Field (
Elderfjeldl, -Hetero-rcycl
ic Compounds”, Volume ■, Willy, 19
57; Written by M.R. Grimmet
”Advances in )ieterocycle
ic Chemistry; Volume 12, Academic Press
Res, 1970, found in. For example, 4,5-dialkyl-2-aminoimidazoliu
Muchloride is B, 'l', Store
y), W, W, X River 7 (Sullivan) and C
, L. Moyer, J. Q r g
, Chem. 29.3118 (according to the method described by 19641)
Manufactured by. acetone and formamide under reflux
heating and distilling the mixture to give 4,5-dialkyl
Midazole was obtained (Scheme 26). In reaction formula 2, R1 and R1 are independently CH8 or C1H! It's I
Ru. p-bromobenzenediazonium chloride to 4.5-
2-(p-bromo) by reacting with dialkylimidazole
Penzena:/) -4,5-dialkylimidazole
(Reaction formula 27) 0 Reaction formula 27 Here, R1 and R1 are independently CH or C1Hs.
Ru. When an azo compound is reduced using stannous chloride in hydrochloric acid,
2-Amino-4,5-dialkylimidazole and p-
This gives bromoaniline (Scheme 28). Aminoimida
The sol was separated and isolated as its hydrochloride salt. ko1:teR and R3 are independently teCH, and ij:ctH
It is i. 4(5)-alkyl-5(4)-alkoxyimidaso
Le is U, Schollkopfl 7 (Schollkopfl and
K. Written by Hantke, Lrebigs Ann,
chem. 1602, (1979), F. Becke and
Pa5slerl, LiebjgS
Ann, Chem, 735.27 (19701 and
K. Huntga, U, Schorkopf and H, H, Hausbelb
Author Liebigs Ann, Chem, 1531 (
19741. By these methods, cyanohydrin has a concentration of 100 to 120
condensation with formamide at °C to form 2-formylaminoalkyl
This gives lunitrile (Scheme 29a). Add this to oxy salt
Dehydrate with phosphor to produce 2-incyanoalkylnitrile.
(Reaction formula 29b). This isocyanide is used as a catalyst
by reacting with methanol in the presence of potassium carbonate,
4(51-alkyl-5(4)-alkoxyimidazo
(Reaction formula 29c). Reaction formula 29 where R1 is CH, also FiCt Ha, and R
2 is CHsO1C*HsO or CH,S. 2-amino-4(5)-alkyl-5(4)-alkoxy
Shiimidazole is a 2-amino-4,5-dialkyl
A method similar to that described for the production of midazole
It can be manufactured easily. For example, 4f5)-alkyl-5(
4)-Alkoxyimidazole is p-bromobenzenedi
2-(p-butyl) by cacipling with azonium chloride.
lomobenbinazo)-4(5)-alkyl-514)-
Alkoxy-imidazole can be given (Shasiku)
Equation 30a). This azo compound was prepared using cuprous chloride in hydrochloric acid.
and reduced to give 2-amino-4C5)-alkyl-5(
4) -Alkoxyimidazole can be given (
Reaction formula 30) Reaction formula 30 (30b) where R8 is CH3 or C* Hs, and Rv
FiCHa O-C* 'Hs O or CH,S
Ru. The aminoimidazole of the formula [a, in which R is alkyl, is a salt
A suitable imidazole is added to an equimolar amount of an iodide in the presence of a
It can be produced by N-alkylation with
Oshiki 31). Equation 31 The N-alkyl product can be prepared by distillation, crystallization or
Can be separated by fi. The 2-amino group was prepared using the method described above.
This can be added by continuous diazo coupling and reduction.
I can do that. 4,5-disubstituted imida obtained by the above method
Sol is represented by structural formula A in the specification and examples.
However, the tautomers or isomers of the product have not been confirmed.
and the compounds of the invention are tautomeric in their production.
It should be understood that it includes both genders A and B.
be. 2-Amino-4,5-dimethoxyimidazole is J,
Qrg, Chem, 44.818 (1979).
Guanidine was dimethylated by a method similar to that shown.
(condensed with DMODIl)
, and can be produced by subsequent reduction (reaction formula
32). Equation 32 The manure example teaches in more detail the preparation of the compounds of the invention.
It shows. Cutting without special instructions, all copies are heavy
The amounts are in parts and temperatures are in °C. Example 1 5, O stirred in a 200-RB Zeta-necked flask
f (0,0385 mol) of 3-amino-5-methylthi
O-1H-1,2,4-) lyazole (Aldringch
chemicals) and 75 m of dry methylene chloride.
, 10.5f 2-(methoxycarbonyl)pen bottle
When sulfonyl isocyanate is added at room temperature, a clear solution is formed.
gradually formed 1°. After stirring overnight at room temperature, the precipitate
The white solid was treated with tF and washed with methylene chloride.
1.7f1 produced a melting point of 147-153°. NMR (tf a-D); δ2.85 (s, 3B
, 5CHs l, 4.10 (s, 3H, Co, CHl
l, 7.60-8.55 (m. ArHl. IR (Nujol): 3.0-3.20
(NH), 5.75 (C=O1, 6, 20 (C=N) mi
Kron. Example 2 Steal method Person: Inject methyl iodide (0.6m) into a syringe at room temperature.
and 30- anatone in 100a/RB/neck flask
0.8f (0,0022 mol) of 2-[(5-methyl
ruthio-IH-1,2,4-)riazol-3-yl)
Methyl aminocarbonyl-aminosulfonylbenzoate and
Add a stirred mixture of potassium carbonate and 0.6f of potassium carbonate.
I got it. The mixture was stirred at room temperature overnight. Then the reaction mixture
Pour into 250-mL ice water and adjust to pH 3 using glacial acetic acid.
Acidified to ~4. Aqueous mixture with ethyl acetate and ethyl acetate
After extraction with a 1-1 mixture of ethers, the organic layer was washed with salt.
Wash with water, dry MgSO4+, filter and
The solvent was evaporated to dryness to produce a white solid residue, which was evaporated to dryness.
Suspend in setonitrile, filter and add acetonitrile
Recrystallized from rill, 0.3F, axial point 198-20
0° was generated. NMR (tfa-Dl: δ2.95 (S, 3
H,5CHsl,4.0 (8% 3H,CH31,4
, t 5 (s, 3H, Co, CH, l, 7.80-
8.60 (m%ArH1゜IR(Nuj o 11
:s, 7 s-5,85 (C=Ol, 6.30 (C=
N), 13. t 0113.55 microns. Method B: Stirred in dry methylene chloride of 15-
1,0f (0,0069 mol) of 3-amino-1-methy
-5-methylthio-IH-1,2゜4-triazole
3. Of 2-(methoxycarbonyl)benzene
When adding sulfonyl isocyanate *-) at room temperature, a cloudy solution appears.
was formed immediately after which a white solid precipitated. white suspension
The solution was stirred at room temperature overnight. Mix chlorobutane (4-)
and filter the white solid, washing with methylene chloride.
2. Clean and then wash with chlorobutane. Of. M point xc+s ~ 200° (recrystallized from acetonitrile
) was generated. Spectral properties and melting point method
It was the same as the solid obtained in A. The mixed melting point is below
I didn't feel like it. Example 3 At θ°, 6.5f of methylhydrazine was mixed with 20.
0f (0,137 mol) of cyanodithioimide carbon dimethyl
Chill's 35117 in acetonitrile with stirring
Added dropwise to the suspension. A yellow solution forms immediately after addition.
, then a white solid precipitated. Remove the water bath and warm to room temperature to form a yellow solution.
, it was stirred at room temperature overnight. - solid after stirring overnight
precipitates, which is filtered and washed with cold acetonitrile, then 1-chlorobutylene? Wash the jar
to produce 8.5f, melting point 104-109°. Sentence
Journal of Qrganic Che
mi-stry, 39.1522 (19741)
reported a similar melting point of 103-106° for the compound described above.
However, the different isomeric structures of the compound (5-amino
-1-methyl-3-methylthio-IH-1゜2.4-)
Specified for Riazole. 3-Amino-1-methyl-5-methy as the correct structure
The designation for ruthio-IH-1,2,4-) lyazole is X-
Proved by line crystal structure analysis. Example 4 2-1:((1,s-dimethyl-IH-1,2,4-t)
lyazol-3-yl)aminocarbonyl]aminosul
acetonyl]benzoic acid methyl ester 20111
0U3f of 3-amino-1,
5-dimethyl-IHl-2# 4) Reasy/L
/ (Journal of Organic Che
mistry13'j,] 522 (19741) and
and 1.49F 2-(methoxycarbonyl)benzene
The sulfonyl isocyanate was stirred for 12 hours. precipitated
Filter the white solid and wash with ether to give 1.31
The title product was produced, melting at 175-178°. Example 5 3-amino-1-methane of pyl ester 0.7f (0,00486 mol)
Thyl-5-methylthio-IH-1,2,4-triazo
and 4. 2-(impropoxycarbonyl)base of Ov
12@l of a mixture of benzenesulfonyl isocyanate
Stirred in dry methylene chloride at room temperature overnight. 1- of 4d
After the addition of chlorobutane, a white solid precipitates and it is filtered.
filtered, washed with 1-chlorobutane and dried, 1.
3f, melting point 192-194°. NMR (tfa-D): δ1.55 (d,
6 H, 2CH, l, 2.90 (s, 3H, SC
H,,l,3.95 (s, 3H,N-CH,l,
4.90-5.40 (m, tH, CO, CHI, 7
．． 60-8.50 (m's, ArHl.IR(Nu
joll: 2.95 (NHI, 5.75 (C=01.6
．． 30 (C=Nl, 13.10.13.50 microns. Example 6 Rubonyl]-2-nitrobenzenesulfonamide 15m
0,7f (0,
00486 mol) of 3-amino-1-methyl-5-methy
ruthio-IH-1,2,4-)lyazole VC3,Of
Addition of 2-nitrobenzenesulfonyl isocyanate
After that, solids precipitated and the suspension was stirred at room temperature overnight.
Stirred. Filter the solid and wash with 1-chlorobutane
and a product of 1.6f, melting point 210-213°,
generated. NMR (tfa-D): δ2.90 (S,
3H, SCH,), 4.00 (s, 3H, N-CH,)
, 7.85-8.60 (m. A r Hl. IR (Nujol): a, o-3,2
0(NHI, 5.80 (C=O1,6,25(C=N
l, 12.70, ], 3.45.13.60 microns. Example 7 1.0f (0,0027 mol) in acetone of 39s+j
) of 2-[5-methylthio-IH-1,2,4-tria
sol-3-yl)ami7carbonyl]Aenosulfony
Stirring of methyl benzoate and 0.7f potassium carbonate
Add 0.8-ethyl iodide to the mixture in a syringe.
and the resulting white suspension was stirred for 3 days.
Ta. The mixture was poured into 250 °C of ice water and treated with glacial acetic acid.
pl (acidified to 3-4.Water t!E acidic mixture
Extract with a 1=1 mixture of ethyl ether/ethyl acetate and
The extract was washed with saline and dried.
O41 and evaporated to produce a white solid residue,
Suspend it in acetonate (IJ) and filter it.
0.311 melting point 188-19]0. NMR (t f a-Di : δ1.45 (t, 3H
, CH31,2,80(s 13 HlSCHs 1.
4.05 (S, 3H%Co, CH5], 4.2
5 (q, 2H, CH, l, 7.60-8.45 (m
, ArHl. Example 8 Methylhydrazine (98H, 6.3 Oflo, 136
Mol l'tN-cyanothiol dimethylcarbonate (17,3
9,0,133 mol, D. M. Ryland, Ph.
D, 'll'hesis, 1971.123-1
prepared according to the method shown on page 24)
Add nitrogen to the solution in tonitrile (35 m) at -5 to 0°.
It was added dropwise while stirring at the bottom. Warm the reaction mixture to room temperature.
The mixture was then stirred for 2 days. The product was isolated by filtration.
Then, when washed with acetonitrile, the white color of 12.7f
It gave a powder, melting point 177-]80°. NMR (DMSO/CDCl, l: δ3.35 (
8% N CHs l :3.95 (s, OC
Hg': and 5.0 (broad, NH, 1° Example 9 ster 2-(7')xycarbonyl)penvin'sulfonyl
Socyanate (80chi, 1.41f, 4.7 mmol)
solution in methylene chloride (1/2) with nitrogen at room temperature
3-amino-5-methquin-1-methyl-IH-1
, 2, 4-) lyazole (0,50 ri, 3.9 mi IJ model)
) was added. Add DABCO (catalytic amount) and react
The reaction mixture was stirred for 3 days. The product was isolated by filtration and washed with methylene chloride.
1.05f white powder, melting point 177-1800.
Gave. NMR (CDCI 3/DMSOl: δ3.5 (s
, N-CH31;3.9 (s, C0ICHs'
;4,1 (S, 0-CH8);7.5-7.8 (m, Ar-H);8,1-8.
4 (m, Ar-H); 9.7. (wide, NHI;
and 11.0 (wide, N) Tl. IR (KBr l 3150 (NHI, 1740 (c
=o), 1700(c=ol, 1600.1530,1
475.1420.1360 (Sot', 1340.1
295.1260.1180 (So, ), 1115 and
1050cm '0 Example 10 2-(methoxycarbonyl)benzenesulfonylis
Anate (0.96f, 0.004.0 mol),
2-amino-4,5-dimethylimidazolium chloride
(0,59f10.0040 mol), ], 5-diaza
Bicyclo[4,3,0]noney-5-ene (0,05f,
0.0004 mol) and acetonitrile (25 m/)
The mixture was stirred at room temperature for 91 hours. The precipitate was treated with n-butyl chloride, 2 HCI
and water and then dried under vacuum at 60°C.
After drying, it gave a white solid. Melting point] 72-177℃
, yield 0.52°NMR: δ 2.0 (s, ArCHml; 4.
0 (S, Co, CH31; 7.2 (bslNHI; and 7.4-8.4 (m%ArH1°
By applying and using appropriate reactants
, the compounds shown in Tables 1 to 18 could be produced. Table 1 Hn-('5H7a CO2°113)III
C2H5(, Co2CH5HHCH(CH3
)2HOE,j42CH3HCH3°2H5,1(OC
02°H3HcH3°2H5HSCI H CH3C2H5 Town OCo2CH5H CH3c2H5°H3° 5o2CH3HC13C,,
H5H' (J CF3- HCH3C2H3H
OBr H CH3C2H3HOCI lCH3°2H5
H8CH3H CH3°2H5° C2H3H CH3°2H5H'0NO2H cH3C2H, HO5o2(CH2)2CH3HCH3
C2H,O502N(CH3)2HLH3°2)150
H3° No2H CH3C2H5° 0CH3H "l"2 P3 w P'? ”8 r,p
-(0C)HCH3C2H5H(, cC2CH(CH3
>2HCH3″:2H5HOC02CH2CH″CH2
H scream 3C2H51! 0 0CF2CF,,HH'
H3C2H5n, t CH20CH3HOCH
3C2H5H○ 0802CHC12HCH3°2H,
H0CF3H cH3°2H5HO5C2H5H O°H3C2H5HO0SO2C2H5HOCH3C2
H5H00S02CH2CF'3HCH3C2H5HO
co2cH2cH2clHOCH3c2H5HO0S0
2CH2CH20CH3HQC2H5CH3HOSo,
, PJ(HCH3)Cl3HC2H5CH3HOCo2
CH5H165-166C2H, Cl3HOBr
HC2H5°H3HON02H C2H5°H3CH30CO2CH3H02H5°J'
13 6H3O502CH3HOC2H5CH3CH
30Co2CH2CH2oCH3HOC2H5c1 (3
cCH30oso2CH2(CH2)2oCH302H5
°F13H8CH3H "l"2 '3! "7 ~ -2
IC2H5CH3HS CI HCH3
C23H30Cl3H 02H, Cl5HCC02CH(CH3),, H
C2H5°H3HO°IH C2H5CH3HO'C02CH2CH''CH2HQC
2H, Cl3H○ 08O2CH2CF2HHOC2H
5CH3H00S02CC13HOC2H5CH3HO
O8C2CHC12HC2H5CH3HO°5O2CH
3H Cl5 Town HOCH2°C2H3H 02H5°H3HO302°2H5H QC2H,°H3HO08O2CF3HC2H56H3
Hoo°F3H QC,, H5°H3H0OCH3H C2) 15°H3HONo25-cv3C2H5C
H3HONo2 3- ClC2H5 Town HO
C16-No. C2H5°H310CF35-No2 C) 13 °2H, HO°l 5-Cl0
cH3°2H, HONo25-CH di ¥, , H011iON(CH3)23-C1)l
l P2 R31dR7"8 m, p, ('
C,)QC2H50H3HOC(120H35-〇2H
5C2H5°H3HOC13-Br C2H3CH3H C15-Br C2H3CH3HONo26-F QC2H5CH3HOC15-F 02H5°d3 h OC14-FQC2H5C
H3HOBr 3-1C2H, CH3HO
Nshi2 5-No202H,
CH3)IQ C020H33-CF30C2
H5CH3HOCH33-No2C2H5'02H5)
1 0 Ct3. , CH3HC2H5CH3HOC
O2C2H5H 02H5°2J(5HS 01B C2H5C2Hc, HONO2H C2J(5C2H5H, S CHy, H
C2Hc, C2H3u c C02CH2a
n duck 82 HC2H5C2H5H C (2CH (C
H3) 2HC2Fi5C2H5HO8'-2CH3HC
2H,c2n5HO5q2(aH2),,aH3,HQ
C2H5C2H5HO5o2CHF2H￥, 02H
5HO502N(CH3)2Hc2H5' C2H
,HO502N(□CH3)C23H5CH3°2H5
)i 0C5O2CH3HC2H5C2H5H○(C
H2),,CH3HC,,H5C2H5HOQC2H5
H C2H5°2H5HO5CH3H C1((OH3)2CH3H0NO2Hdan-03H7°
H3HO°l' HCH2CH(CH3)2CH3
H0Co2CH3IICH2CH"C, H2CH3H0
CF3HCH2C(CH3)<H2CH3HOCo2C
H5HCH2CTIICHCH3110Go2°+(3
HCH2C″cCH3CI3HOCo,,CH3HOC
H3CH2CH<)I2HOCO2C2H5HCH3C
H2C(C13)=CH2HO5o2CH3HC13C
H20H-C: HCH3HOCo,, CH3HCH3°
H2°ECH3H0CO2°H3H to CH2
C'''CHHONO211SCH3CH3CH3°No
2H 8CH3CH3CH3O502N(CH3)2HRIR
2R3W17R8(oC) SCH3cH3Ch3O502N(CH3)C2H5H
5C) I3CI35 CH3I SCH3°113HSNO2,H 3CH30H3HOCL H230737 E, C1136H3I O0502C13H5CH
3CH3HOCo2CH2'; H2CH3USCH3C
I(3HOCo2CH2CH=CH2H160-63 SCH3CH3HOCo2CH2CH2Cl H8
CH3CH3110Co2CH2CH20CI'13H
SCH30H3HOCa2CH(CH5)C2H,H3
CH3CH3HOCo2(C12)3CH3H9CH3
CH3HOQSO2(CH2)3CH3H5CH3CH
31+ 0 0SO2(CH2)30(:H3H5,
113CI3HOCH20CH3H5CH3CH3H○
0802CH2CF2HH5 Town CH3HOHH ScH36H3HOF H2O)t3C
I3HOH4-F scit, °H3HOH5-FSCH3°H3
HO0s026H2CCI3H-shi ”3 H%
”s ('r+, tSef13CH3H
O0802CH2CHC12H5CH3CH3CH3°
S02°H3H9CH3CH3HO0502CF3H 5CH3CH3HO0502C1iC12H5CH3C
H3HO5o2(CH2)2CH3Hsea3CH3H
O5o2N(,:H3)2H5CH3CH3Ho,5o
2N(C2H5), H8CH3CH3HO5o
2s(aH3)(aH(CH3)2) H8CH3CH
3HOS(,2CH(CH3)2H8'shiH3CH3I
I OCH2CHH5' H5CH3CH3HO
C2H3H 5CH3°H3IOCF3H 6CH3CH3HOC15-Br SCH3°H3HOC16-CI SCH3CH3H,ON025-CI SCH3CI(3110Co2CH53-BrS01(
3°H31105o2CH34-OCR3SCH3°H
3HOC02G134-OCR3SCH3CH3H-O
C15-No2 SCH30H3HO502N(CH3)25-No2S
CH, CH3'HOC15-CH(CH3)2m, p. Part H3°H3HONo25-C2H5, T, Cl5CH3HONo25-CF5SC113C
I3H("No23-CF3!l', cH, CH3,
HOFo-, CF3H5ZH3CH3HO0CF3H 5CH3CH3, HON026-F SCH3Cl3 HOC15-QC2H5SCH3
°H3HOBr 5-No2SCH3°H3
11° No23-F SCH3CH3HOC1U-F SCH3CH3HONO26-F S3CH3HCC14-F S0H3CH3H00S02°l1F2HSCH3CH
3HO0S02(C112)3B! -HSC2H5CH
31i 0 Co2CH5H205-2085(
,,H5°H3HO802cH3HE',C2H3CH
3CH305o2CH3H! CH3OON to 5C2H5
o2H186-190SC2H5CH3HS CI
HSC2H, CH2OS CH3H DC2H5CH3HOCF3H
SC2H5'Cl5HOCo2CH(CH3)2H15
,'-156SC2H5CH3HOCo2Cl12CH
<H2H172-174SC2H5°H3CI・3ON
02H 8C2H5CH3H, (: 5o2t, H5Hr, c
2n5CH3HO802N(0M3)C2H,HSC2
H5OH3HOBr Hs(', 2kI5C
I3HO0CF3HSCH3(,,ll5HOC1:)
20H3H5CH3C2H5HOCL H8
CH3°2H5HONO2H S0H3°2H5H8Br H5CH3C2
H5HS CF3H 5OH3C2H, HOCF3H 5cH3°2H5HOOCH3H 5CH3C2H, HOCo2(C)I2)2CH3H8
cH3C2H5H00S02(CH2)2CH3H5 beating
3 °2H5HO502N(CH3)C2H5H5CH
3C2H5, HO502N(OCH3)OH3H5CH
3C2H5HO5o2(cH2)2co3H8CH3°
2H5HO0CHF2H SCH302H5H, OCR(CH3)2H"l
'2 '3 W "?"
8 (0C)OCH3°2H5HO3CF3H 5CIi3 C2H5H○ O
2O3(CH2)2ocH3HSCH3C2H5H05
C2H5H 3(CH2)2aH3CH3HOCI Hs
(r, H2)2CM3cn3HOC02CH, HSCI
n to I(CH3)2CH3HOCC2C2H3Hs,,
)3°)i3CH3HQS02°H3H5(':H(C
H3) C2H5OH3HOC0262H5H8CH2C
H'''CH2CH3H0NO2H=, ca2c(cH3
)=CI(2CH3Ha Co2C13H8OW2CH
=CHC113CH3HOS○2CH3H8cH2C'
-'2°H3°H3HOCI HSCH2C
o2(CH2)3CH30H3HOBr H
SCH(,CH3)Co2CH3°H3HONO2HS
CH2C'MCH' CH2OOCo2°H3H5
CH2C″cCH3cH3HOc02CH3HCH3°
H2°0H3HOCo2C,, H5HCH3cH2°C
H3HO802°2H5HCl3. CH2543
HOCH20C di HCH3C) I2CH20CH
3HOCI HCl3CH2CH2SCH3
1+ O502CH3,HRl --35
18・',,)'"H2〕"]2H5°H311
・CH3' (C0262H5 gate HCI C02C
H(CH3)2 HOH20°,? )H5CH3°H
3'"0'-2°H31(CH20CR(CH3)2
CH3HOBr II (:H2,,CCH2
>3CH3CH3HL E, 02C21 (5HCH2
CH20CH3CH3ru ONo2HCH2C12Q
C2H, CH2O0CO2CH3HCH2CH20(C
H2)2CH3CH5HOC02CH31(OCH3C
H3H5C1H OCH3C2H5HS No2H OCH3c2H5HScH3H OCH3CH3HS CF3H times 3 CH3H5Br H times 3
°H3°H3° 002613 HOriH
3 Town Town O5O2CH3H OCR3 Town CH30 Minoh H3H JiH3 Town H00S02(CH2)30CH3HOCH
3C2H51t00sO2CH2CHC12HOCH3
C2H5) 1 0 08020H2CF2HHOCR
3C2H5HO0CF3H OCH3C2H, HO5CHF2. H1ゞl
R2H3V7' (7~ 沫)・TH3C2H5HO
O3C□P"H (CH3) 2H part 2H5CH3II
OHH, ;C2H5ZH3h t゛F
HQC2H5°
H3・l0C02°H33士C:;2H5CH3if
O5o2CH3H190-208t-+c2H5CH
3+; o 5(CI(2)3cH3HOC2H5
CH3HO0SO2 (CH2), CH3HO°2H5C
H3140°CF3 H flash 2H50H3
+1 0 5cv3a QC2H5CH3If Q 0CHF2H'''c2
H5°H3II O5CHF2HGC2H5CH3I
I O0CF2CF'2HHα:2H5CI3)i
0 5CF2CF2HIQC2H5CH3HO0M2
QC2H5HQC2H,CH3”)! OSCI[3
HQC2H50H3HOCo2CR2CM2CI
HoC2H5CH3Ho Co2CH2CH=C
H2BQC2H5C)! , fl OC02cH (
CH3>2HoC2H, CH3I O08O2':,
HEY312H” HOC2H5°H3HO0802C
HFCCI3HQC2H5CH3, HO0802CHF
CH2F MAll”2 R3v; R7
'3 LX20C2H, C113HO0802ji1
2CH,,Cl2Hα:2H5CH3HO502N (open
3) 2 H169-Near 5
QC2H5CH3HOsc2+1(CH3)+'(CF
12) 2an3) HoC2H5CH3HOqo2q
n2an(qn,)2HQC2H5CH3HO0CH2
C): (C113)2Hα', 2H5CH3HOCo2
CH3+1 187-189QC2H5°H3CH,
O5o2Cl, HoC2H5CH3°H
3OCO2°H3HOC2H5CH3CH300SO2
CH(CH3)2HCC2H5CH3CH30CF3H QC2H5CH3°H, O0CF2°F2HH002H
5C2H5CH30CI HOC2H
5 to 2H5HO5C) IF2 HoC2
H5CH3HHO5o2CCH2>20H3HQC2H
5C2H5HOCo2C2H, HOC2H5CH3HO
O8O2 (Crucible 2) 3C1H"-("tsuR2),,0M3
CH3I OC1, HOCCH2>2CH3CH3I
I OC2H,' I(OCR(CH3
)2CH3n o co2ci(<CH3)2HC(C
a2) 3CM3cH3I Oco, aH3HOCH2
CH=Ck12Cki3HO,'502cEi,
HRIR2R3,, R7~i4 presentation 810C
H2CCCH3>-Co2CH3+1 U C02C
H3H(,cO°H2C1”CCH3CH3I O(
X2CH3H father 0CH2 return: HCH3H' OC02C
2H5HQCCF3CH3HOC02CH3HQC CF3 CH3HOCI H()c
CF3C2H, HONO2HQC CF3 °2H5HONH3HOCCF2C
F3CB3HOCo2CH (CR3) 2H head CF2°F
3CB3HO 2CH3HQCN(OH3)20H3H
OC(20H3HQCCF3C15HOC02CH3H
QC CF3 °2H5HO, CF3H0CICF
3 °2H5HOcH2″113HOLrS
CH3CM2CM“CIH2HO,C,,;2C13H
146-1490CISC2H5CH31(OC)13
15-CH3193-1950CI8C2H5C2H5
HOC02CH3H150-152oclCl((0M
3) 2CH3HO' Co2CH5H190-19?
clG'. 0CH3CH3HHHH0CI OCH3cH3,HHCH3I 210-213
JR2F'-3Vi '7 ''8
al(3CH3I H”H(CR3,)2”H3CH
3HH(niH2)3CH3H H3(Ii3HH0CR3H H3CH3HH0CR2C) 13H 1(30H3HH0CR2CH2CH3H154-15
7H3CH3HH0CR(CH3)C2H5n1(3C
H3HHF H)13C)i3HHCI H#205H3
°H311HBr HH3CH3HHNo
2H185-189H3CI3HHCF3H H3CH3HHC02C2H5H144-148H3C
H3HHco2(CH2)2aH3H117-120[
13CH3HHCo2CH (C13)2. H165
-1691(3CH,HHco2Cn(co3)c2H
5H(3CH, HHco2(CH2)5c+L3H1(
3C) 13HHCo2CH2CH<R2H139-14
4H3CI3HH2°H20M<HCH3H(3CM3
HHCo2CH2C HH R1! '2 h3! Saka version = Zenji (JCH
3r:H3+r G ca2aH2tn2o', 2
H5HOCR3CI3HOT02E12)3(C21(
5HO°H3'::H3HO12CI112Z鴫C2H
3H concave H3CH3F, Q C; 02CF2CFH
2HOCH3CH3HOCo2CH2CH2-F
HQC)I CH3HOCt・pc! (2CHF'
:F2HHOCH3CH3i1 0 502N(CH3
)2H183-1860CH3Electric ZH3HO502N(
C2115), HOCR30H3HO502N
(CH3)C2H5HOCR30H,HO502N('
;H3)CR20M2CR3IOCH30H3HO50
2N(OCH3)C13HOCR3CH3HOQSO2
CH3H174-176ocH3CH3HO0302C
2H5゛HOCH31-R3HO, OS' given CH2CC
H2CH20H3HOCH3CI, o csc2
an2an2ocn3HOCH3CH3HG 0SO
2CF3HOCR3°H3+I C0SO2CFi2
CH2C1H00H3°: H3HO5OCH3H O°H30H3HG 5C1i3)10CH30H3
HO5o2CH3H183-1900CH3CI3HO
5C2H5H ``l K2 ''3 t+ '7
'b m,;:,('',:)QCH3CI3
HQ Z″′,,°211.) IOCH3
CH31i 0:;02CH2C)12CH3H
1%-Eng.770CR3CI3 Summer (O5C2(J((
CR3)2HOCH3Cd3 Hu 5C3
(C112)3C13)10CH3CH3H○ Sy2
OH2tm=cI1211OCR3CH3)! CS
F3I+OCH3°113HOSO2:1i2C in O2
12C11100H3CH3HO502CF2CF31
+ Engineering H3CH3HO5o2CCI2CF3HOCR3C
H3HON(OH3)S(,2α13HOCR30H3
if ON(C1(3)SO2C,,H5HOCH3
013HOrg(CR3)SO2(sH2)3cH3H
OCIi3CH3HCI N(CH3)502CH2
CI+20CH3) 10CH3CH3 yo 1C',
i size (CH3) 5'-12CF3 ao
cn30H3H (, N (CR3) engineering 20H2C1 (2C
L HO°H3CH311CCH2(X)2CH3Ho
CH3CH3HOCH2C02C2H5HocH3CH
3HOCH2C022(CH3)2HOCH3Chi3
HO0H2C02CH2CH20CH3HOCH3CH
3HOCH2C02CH2cH2C1■0c)I3CH
3HoCH2CO2CH2CH″FI2H+(l
H,,R,Tachisha Yu-niyo0CR3CI'3
h '-' CH(C・13)002°113)
1vCH3C113H'-C112SCH3H (CR3
Cl, HQ: ;n2soC2H, HOCH3°
H3HOCH25o2C1 (3HOCH, C13HOC
H25020H20H″CH2HOCH3CH31mi
CI Cl2So, CF, HOCR3CI
3II O':H2S02CF2CF3HOCH3e
l13Hi・CH2502CH2°H2C13I! 0
CH3CH3HOq+1(CR3)s++2aH3HO
CH3CH3ti ○ 0CII2CH″0H211
0CH3CH311C,O';1(2f;H''CHCH
311vcH3CH3HO0CH2(jCHHt)cH
3CH3HCCH2°H20°H3'+(OCH3ri1
13HOCH2CH2QC2H,H(X';H3CI!
3' HO0CF3. HO°H3CI(3H“
)0CF2CF3HOCR3CH3HOOt;H2
CH2CL HOCR30H, M OjiH2
CF2CF31 (OCR3CH3HQ CeH2°C
H3HOCH3CH31 value 0CR2C12
0CH3HOCH3CH3HtJ UCH2QC2H
5HRI R2R3A,%'
-,,,,,(”・)CCH150H,HO0CH2
ZH2°c21 ■ 51+v, :H3CH3HO -I"
R3,) IOCR3CH3H! '-CI2°:2B5
, uOCH3CH2Cl73 HC:(”2
1shi) 13 Hlno4-1J
, QOCH3CH2CF3 II OSe 2N
(CH,)2 1i 150-L
L+700H3°H2CF3HOC1)i 9O-1
6Cocli3CH2CF3HOS02°+13
1j 195-2270CH30H2CF3 I
I LI No2
'+1 158-160QC2H
5CH311Q °H3H QC2H5CH3HQ CH2CH3I+QC2H,
CH3)i 0 CH,, (C13)2HQC2H
5CB3II OBr HQC2H5CH
3HONo211 OC%5CH3HOCF3H CC2H,, CH3I Q Co2(C:R2)5
CB3HQC2H5°￥3 HO'tsu02<1(2CH
20CH31+0C2H, CH3I OCo, 2CH
2CHCH, HQC2H5CH3HON(CH3)5o
2CH3HQC2H5CH3HON((:R3)So2
C2H5H1111 5! R7 class = Eni
RkoC2II5 °II3+1 '-0S0
2cl13H'c1゜QC21(, CH March Or, t
;2C112CJ (2°H3”C
H=CH2CII, ](ODo22H2CH
″C■i2 + (c1CC2)i, :
1I311 0 Go2CF3Hc10C2H5C)
i3HO”: H2C02CH, Hcloc2n5cn3
)I Q c+r(an3)CO2cu3Jl
0106%, FH3i1 F
C) i2Co2Ci (2CH2CI HCIQC
2H5CH311'= C,1-12So2C1(,
Hc10°2H5°H3110'-1i2SCH3Hc
. QC2H5C1 (3HO=tsuB3)sp2cH3Jl
clQC2H5C1131100CH
2CH=CH2HcIQC2H,CH3,HOu22C
″CcH3HCIQC2H, CH3I OCH2°C
H3Hc1″2H5CH311OCH2 Morning 20C21I
5HclQC2H, CH3' HQ 0CFfF2
CH3Hc10C2115°H3HO0CH20CH3
HclOC2H5CH3H00CH2CH20cH3H
cIQC2H, CH3II O0GH2CH20CH
2CH3HclOc2H5CH3H00(CH2)30
cH3HclCI CH31i 0 °”3
HClCl CH340'CH(
CH3)2HclR2R3w R? h,
:, m, , ('c,)CH,HC0CH3H town )I Q 0CH2CH2CH314CH3H
OCI H CH3HONo2H CH3I OCF3H CH3I Q Co2CH5H CH3H0C02°21'15 H immediately 3HOC
O2CH2 report = CH2H CH3HO802N(OH3)2H CH3HO0SO2cH3)■ CH3I ON(CH3)5o2CH3HCH3HO
So2CH3M CH3HO502CH2CH2CH3' HCH3,H
OCH2Co2CH5H CH3HOCH=CH3' HCH3HOCH
25o2CH3H CI'L3HOOCH2CM''CH2H Town HOOC
H2 Tsutomachi H CH3I OCH2C, CB, , HCH
3HOCH2CH20CH3H CIL3HOCR2CB20L H”l
"2"3W'7 Yuuni NHCH3CH3HO
C) I3H NHCH3CJI3HOCH2CH3HNHCH3CI
I3HO0CH3H NHCH3C1i3HOBr HNHCH
3CH3HOCI HN'HCH3°JI
3HONO2H NHCH3°H3If OCF3H NHCH3°H3HOCo,, CH3HNHCH3CH
3HOco2aH(an3),, nNHCH3C
H3HOC02CH2CH2Cyu HN
HCH3CH3HOso2N(cg3)2HNHCH3
C:H3HO5o2N(oca3)ca3HNHCH3
°H3HOO802CF3HNHCH3°B3)1 0
502CH,HNHCH3°H3' HOSo,C
H2CH2CH3HNHCH3CH3HO502CH2
CH″CH2HNHCH3 town Ho cCH2■2CH
3HNHCH3CH3HOCH2CD2CH2C1 (2
CI HNHCH3'T(3HOCH25OCH3H
NHCH3CH3HOCH2502CH3 TownNHCH3
' CH3I OO°H2°H″oH2HRI
R2R3W L Yu-Yu NHC
H3Cl311 0 oCH2c=cHHBCH3CH
3HQ CH2502CB3. IINHCH,
CH3I O,0CH2CF2CF, HNHC
H30H3HOQCH20C1 (3HNHCH30H3
HOQCH2CH20CH3HN'I (0H3>3HO
ocI(2CH20C2H5HcH(acn3)2cH
3Ho cH3HOH(OCI3)2CH3HOan
(aI(3),, rtCH(OCI3)2CH
3HO0CH3HCH(OCI3)2CH3! I O
0CH2CH2CB3HCHCOCR3>2CH3HO
,' F HCH((X:B3)2CH3
HOCI HCH(OCH3)2CH3HO
Br HCH(OCI3)2CB3HON0
2HCH(OCI(3)2CH3HOCF3HOH(O
CI3)2CH3HOCo2CH5HCH(OCH3)
2C13HOCo2Co2C2H3HCH (OCH3)
2COCo2CH2CH=CH2HCH(OCI3)2
Cl, HO802N(CH3)2HCI((OCH
3) 2CH3HOs02N(CH3)C2H5HCH(
HCH3)2CH3HOO802CF3H R2
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H3)2CH3HO8○2CH3HCB(OCH3)2
CH3HC5o2(:H2C)12CB3HC(OC
H3) 2CH3HQ 5o2CH2CH=CH2,'
HCl1(OCH3)2CH3H(,cH2a2cH3
HCH(OCH3)2C13HOCH2Co20H2
H20CH3Han(aCH3)2 CH3I
OCH2;3U2CH3HCl1 (OCH3)
2CH3HO0CH2CH=CH2HCH(OCH3)
2CH3H, O0H2cH20CH3HCH (OCH3
)2 °H3HOCH2CH2Han(ocH3)2
CH3HOocH2cH2ocn, HCH(OC
H3)2CH3HO0CF2CF,, HCH
(OCH3)2CH3+io ocH2cr2a
F, H-1〕 (:HCH3OOCH3H Cl CH,HOCu(cH,)2H ゝO 0 (:Ho, 7 CH3OOQC;H2°H311翫'°〕 CH0H3HOCL H ■ R, R2R3V+ R7yu set aim'°) Cost .H3k“ °”02 ”11O〕 C)I CH31+ ° CF3I+O ;〕 CHCH3OOC02CH3H Flight.,] CH3HOC02CH2CH2CL
HIO] It's C. l:H3HOCo2co(cH3)
Hl:〕 CH0H3HO502N(CH3)2H10〕 C嬰. CH3OO5o2N(ocir3)cH3H
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5c3゜”J OH, 11, 05o2CH2O
H,, CH, H 碩°〕. Yo, 1. . CH2Co2C
H,,H2C 0H) 0H3If OCH(OH3)Co2CH3
H\0 (Cl CH,If OcH2SO2CH3H(](
. '] CH3OOCH25C2H5Co CH3O
O0CH2CH=CH2H−〇C? . ]CH3HOCH20CH3 (Jl:]CH, HOCH20H20CH, HCH'J
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R2R3Vr )'7 ”8
dc/H'1CH3,HO0C)12CF2CF3H
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HOCo2NCG)+3)02H5HOCH3CH3H
c cc2N(CH3)c+(2Cu2an3HOc
H3CH3HOC02(CH3)C6H5HOCH3C
H3HOCo2N(CH2)4HOCR3CB3I
OC(0)SCH3HOCR3CH3I OC(0)
SC2H5HOCH3CH3HOC(C)SCH2CH
2CH3HOCR3an3Ha c(o)sea(C
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2HOC2H5CH3HOC02N(C2H5)2HO
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2H, CH3HOCo2N(OH5)CH2CH28H
3H"l R2R3W'?"
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Hoc2;+5CH3HOc(a)sCH3HC,C2
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3I OC(0)SCH2CH2Cl3HQC2+5
C+3HOC(0)SCH(CH3)2HSCH3 gates
HOC02N(CH3)2H5CH3' Cl3HO
Co2N(02H5)2H5CH30H3HOC02N
(CH3)02H, HsCH3CH3H, OC02N(
CH3) CH2C112CH3H3CH3CH3HOC
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53CH3oC02CH2CH20C)I3H5CH3
CH3H,OC1-CB(CB3)C2H5H8CH3
CH3CH305o2(CH2)CH3IOC2H50
2H5) 1 0 F H--sa! notepad
5-Eko CF3 °2) 15C) 13= G 3Q2'koH
3H8CH3°H3°H305c2n(o°H3)CH
3I00H3°H3HOCH3I (ICH30H3HC: CH(CH3)2nOCR
3CH3+1 0 00H3H OCR3C83HQ 0(CH2)3CH31i0°
H3Q'r3HOBr HCH30H3H
OCF3H 0CR30H3)i 0 C020H3HOCH3
CH31i Q C02C2H5HOCR3C11
3HOco2c)I(c)13)2. , HO°H
3°H3HOC'J2°H2°H2°H2CH3HOC
H3CH3HOGO2C)l, CH2Cl HCH
30H3HOC02CH2CH=H3CM to CH2HO
3HQ 502N(CH3)2HOCR36H3HO
502N(CH3) to 2H5HoCH, Cl5HO50
2CH3H )ll '2 "3 W R16"l?
'm,pJoc,)OC113CI3HO5QCH3
H OCH3CH3HO5C113H OCR30H,)i 0 SC,, H5H(X';
H,,CH3)i 0! 302C2H,HCH3
0H3= HO502CH2C112 Town HCH30
H3HO5o2Cl(CH,)2HOCR3CH3HO
502CH2CH=CH2H (X: H3°H, HO5C
H20H''CH2HOCR3CH3HO502CF3H OCH3CH3HO5OCFCF H23 QC2H5CH3110C1' H QC2H,CH3II OBr HQC
2H, CH, HO5O2CH3H QC2H, CH, HOCo2CH5H QC2II5CH, HOCo2C2H, HQC2H5C
H3HOC(12CH2CH″CH2Hoc2H5CH
3HO802N(CH3)2HOC2H5CH3HOC
H3H QC2H,0H3HOCH(CH3)2HQC2H5C
H3i 0 Co2CH(CH3)2HOCR30
H2CF3HOCL H”l ”2
．． R3:'+ R16"17 riocH3C
M2CF3HO,5o2CH3HOCR3CH2CF3
HO5o2N(CH3)2HOCH3CJCF3Ht)
C02CH3HccH3C112CF3HL,I
Br HCI CH314='
“;1HCI CH3HOBr
HCl Town HO'CH3'
HCI Ch3ts O, OCH3HCI
0M3H0C13H CI 0M3)i Q C02CH3HC
I CH3I OCo2CH2CJ(”';
H2HCI 0M3H, O addition 2FT (CH3
)2 HCI CH31i 0 5O2
cH,)lNHCH,CH3I OCL
HIJHCH3cH3II OGo26H3HN'H
CH3°H3HO5o2cH3HCH (HCI3>2
0H3HOCl
HCH(OCH3)2CH3HOty=, no CH3H 0
CR3)2”(3u o 5o2N(CH3)
2) 1 table 4 B8 ”l R2R3V: ”17 ”18
”Point (C) 11 C2H3HCHC:02CH
,. I n-C,H7HO' )i Co2C2H
5CH3°2H5HOHBI- CH3CH5HQ HCo2CH (C:B3)? 0H
3CH2CHCCH3>2HOHC02CH3CH3C
2H5HOHNo2 CH3C2H5H (JHH CB302H5HS HCl CH3C2H3HOHCI CB5C2H5CH30HCo20H2CH"CH2C
H3C2H3II OHCo2C112CH2CI
CH3C2H5CH3CHCo2CM30H3C2H5
'CH30,H5o2CH3C2H5CH3CH3
° H5o2a13C2H5CH3cH30HOCH3 CH3C2H5CH30H5o2N(CH3)2”l
)12 R3M R17R18 Nigayu) CH3
°2H511,3HNo2 Town C2H3HOH5o2rv(OH3)OCR3CP
H56H51: S)] So2diC2H5
CH31" 05-FSC2°H3C2H5CH3H
O4-F Br CH3C2H3HQ 5-CI BrCH3C2
H51! 0 5-CH3'l: 1c2H5C2H
,HOHBr 02H562H,HOHC02°H3 C2H5C2H5HOH5o2CH3 C2H5C21t5HOHso,,N(CH3)c2u
5CH3C2H5HOH5o2(an2)2z3C,H
, °H3HOH-JCH3 C2H5C2H5°H3° H5o2CH. C2H>C2)I5CH30HCO2CH3C2H5°
2H5HOHH CH362H5H,05″″FH CH3C2H5HO5-CI H C2111,C2H3HOH5o2N(an3)202
H5°2H5H5HBr CH3C2H3HOHF '22°RI R25 standing -52C2H5C2H5110il F knee L;
3H7°H31i t) HCt'2GH3CI(C
H3)2CH3HOH,5F12CH3C1(2CH(
CH3) 2 CH3 Summer 1 (: lI
C('12C2H5CH3n<3H7110
11Br CH3C2H-cH2HQ H' Co2CH (C11
3) 2CB3CM2G ((”, B3)=CH2HiJ
HCo2CH3CH2': H°CH2CH3HOli
C2H3Ct(2C(C13)咄C1(3HQHS
o2CH3CH3CH20″ceH3HOHC02CH
3CH2CICshiC)L3CH3HOH5o2C2H5
SCH3°13 H-y 11 Br5C
H3CH3CH3°11 Er5C, H3CH3H
O4-CI BrSCH3Cm3HO5-0CH3H SCH3CH3HO5-CI Cl 5e113CH3HOHNo2 SCH3CH3HOHSo, N(CH3)C2H5 turbidity 3
CH3n OH5o2N(an3)(an(!;n3
)2) SCH3°H3d O, HF S tap 3 □ HO5-yl("l '2
"3 V-"17 "18 upper) S
C) 13CH3) 1 0 4-Br H3CH3C
H3HQ >-Br H3CH30H3C1130
, HSo2°)! 3SCH3cH3Ht□ 11
C02013200-202SCH3CH3CH3t
+ H5o2N(CH3),. 5CH3CH, HCHQC2H5 SCH3CH3HS HH 3CH3CH, H+-i HCo2(CH2)3CH
3SCH3C) I3HOHC62°H2C) 120°B
55CH3CH3HO5-CI H 5CH3CH3HU H0CR(':H3)C
2N(5S':H3OH3HtJ 5-CH30H3
SCH3CH3HOH5CH3 SCH3CH3HQ H5(CH2)3GW3SCH
3C,4,HOH502C2H5SCH3CH3HOH
Co2C11(CH3)2SCH3CB3HOHCo2
Cl2CH=CH2ScH3°,,H5HOGo20
H. SCH3°2H5HOHBr 5CH3C2H5HOH5o2CH3 SCH3C2H5HS HC1 "l '"2
P3 v+ '17 "18
! ! ! 11.4. ! ! 14, j! ;::II:1)
SCH3C2H,H(・II N02SC2H5C
H3h OHtsu02CH(';...3)2SC2H5
CH3H<, HCH3 1sc2H5CH3+・ (HCu2CH3SC2H
5CH3h Q H5o2Gl(3SC2Hj
CH31i 0 HBr5C2H5Q
i3 °; H30HCl5C2H5CH3HS H
Br 5eH(CH3)2CH3HQ H flash 2CH3S(C
H2)3CH3CH3, H(111S()2di5CH2
°H==CH2C1i3H(HC42Cl.S(':H2)2CH3CH3)1=H,C(
12CH3SCH2C(CH3)=CH2CH3HOH
CC2C,, H5SCH2°? CCH3CH3HOHC
c2CH3sCH2CO2CH3CH3HCHNO28
+:H2C02(CH2)3CH3C)13H(I
H(102CM.5CH(CH3)Co2CH3CH3H'OHCo2C
H130CH3CH3HQ HC02CH3183-
1860CH3CH3HOH5o2N(CH3)C2H
. OCH3CH3H' OHBr ■H3 hit, HOHCI RI R2R3Vt "l'7 R18 2nd ward 3
〇Cll3 °113HOHNo20CH3C1!
3Hε H5o2CH30C113CH3CH3<:
HS','+2CH30CII3CH3H,"H5
o2CH30CIi3CH3HOHSO2(CH2)2
C] (50C143?H3HOH0CH3 QC2H, CH2OOHQ(CH2)3'; H3QC,
H3CH3HOHCo2CH2CB<H20CH3CH
3HQ HCo2CH20H2CIOC1i3C2H
,HOHCo2°H(CH3)20CH3C2H,HC
, HCo2(CH2)2CI3QC2H5CH3H(!
H', 02C2H50CH3C2H, CH30HC
O2CM3C02C°21 (5HS H'1 0C2H5CI'3 Hm HBr times 3 °2
H5H. ,:'H8O,,Cchi0CR3C2)T,
HOHSC2(0M2)3CH30CII3C2H,H
OH5o2ctr2Ca(CH3)20CH3,C2H
5CH30H5O2CH30CH3°2H5CH3Q
5-CI 5(j2CH30C!(3C2H5,C
H305-Br 502CH35 5 Qiuyu
Paramotor upper rank) OCH3C2H5HOHQC,, H3 OCH3C2H511 (7iI FOCH3C2H
5HQ 5-F FOCH3C2H5i・QH
SC2H. QC2H50H,H[・B 502N(OCH3
)CI3oc2H,0M3HU Hso,,N(CH
3) ((r+t2)2cH3)QC2H5CH3HS
)i, HOC2I (5CH3H5HN02 QC2H5CH3HOHden2CIIC=Hs)2QC2
H, CH3kl OHC (12CH2C:ll2CI
QC2H,'0M3i・0HCH3QC2H,C
H311c Hch(CH3)2QC2H,CH3)
i 0 ) I C112 to H(CH3)2QC
2H, CH3cu3 ° )I C13QC2H
5CH3CH30H5o2CH3QC2H, Co2CH
2CB CIQC2H, CH2OQ HC2H5 0C2H5CH3HOI (NO2 QC2H5CB3HO4-Br k oc2H5 (13Hc, b-alCI QC2H5C,H, HOHC1 ”IR2N3 ☆ R17Rls 肚 rise) (K
:2H5C2H, HQ HCo2CH30C2H, °
2H5) lQH502CH3suC2H, C2Ii,
)i, G, H5o211(CH3)2Q
C2H5C2H5HQ HNo2 utj2H5C2H, Ij OHBroe2H5C
2H5HOn Co20H(CH3)2″H3C2H
5HOH5IJ2C21 (50 towns C2H,)
! 0 4-F FQC2H5CH3HOH0C
2((CH3)20C112CH=CI2CH3HOH
5G2CH. ocn2c(CH3)=co,, CH3I OH
Co2CH5c:n(CH3)c2u5CH3H(HC
o2CH. QC)I(CH3)2CH3)i 0 HCo2C
♂50(CH2)2CH3CH3■ ○ HCl0CH
2C”CH2CF3HOH!io2CH20CH3CM
3II OHBrCH20CH3C'H3HOHC
I ClCH20C' CH3CH30H5o2C13c
H20CH3CH3CH30HC02CH3CH20C
H3CH3HOHC02°H3CM2(X:H3CH3
HQ 11 No2)ll
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1---CH20CH3CH3H! ', M Cl
0H20CH3CH3'ii O)i HCH2
0CH3CH3Hi II 5o2N (CH3),
. CH20CH3CH30H30H5o2N(CH3)C
2H. CH20CH3C2H5HOH8O2C2H5CH2Q
CH3°2H5HOHC02°H3CH20C%5CM
3)10)] BrCH20CH(CH3)
2CH3HoHCO2cH3aH2o(an2)3ca
3CH3HOHCo2an3CH2CH20CH3CH
3HOHClCH2CH20CH(CH3)2CH3H
OHco2cH3N(CH3)2CH3HOHCo2C
H5CF3CI(31(○H802cH3 CF3CH3HOHCo2CH5 CF3C,H5HO)l co2cH(CH3>2C
F3 °2H5HoH5O2CH3CF3
°2H5HOHBBrCF20F3CH3HO
H'Co2cH3CF2CF30H3HOHCl 0H3CH2CCH3HOHCo2CH3G13cH2
,5CH3HOHC1 ”l R2”3 W R17R18aCH3°H
2CH2°CH, HOH'co2°H3CH3CH,,
CH2DCII3HOHBrQH2°CH3°,,H5
H1,,HC02°H3CH2°CH3°H3CH30
H2(1(3QC2H5CM, c1130 H
5o2(CH2)20H3QC2H5CH3H(,n
5o2an(CH3)2QC2H5>,
Summer 1 0 H5O2N (C2H5) 20CH3C
H2CF3HOHCo2CH3152-1550CH3
CH3110HCH3 0(:H3CH3HOHC2H5 0CH3CH, HOhan(cH3)206H3CM3
HCH0CH2CH2CH30CH3,CH3I O
HF QC) 100m13HOHCO2°2H50CH3CH
3HOHcO2CH2CH2oCH3oCH3cH3H
OHcO2CH2CH″cH20CH3CH3HOH5
o2N(cH,)2OCR3CH3HOH5o2N(O
CH3) CH30CH3Cl, HOH802C
H2CH42QC2H5CH3HOHF QC2H5CH3HOHC1 ”l R2'3 V+ R1? To R18-
D0°2H5°H3HOHBr QC2H5CH3HCHCo2CB319+, -197
0C2H5CM3HCH5o2N(CH3)2QC,H
5CM3it Q H5o2CH. oc2H5°H3HU H5o2CH2CH″C
H20CH3CH2CF3HG HCH300H36
82CF3 H(J HO°H30CH3
CM2CF3HL HCl 0cH3CII2CF'3M0HN020CH3CH2
CF3 HOHCsu2CH2CH30CH3C)1
2CF3HOH5O2N (CH3) 20CH3C Summer■2
CF3 HOH502CH3CI CH3I
, OHCH3Cl 0M3HQ H0CR3 CI CH3I CHCl Cl CH3I OHNo2 CI CH31(CHCo2CH3Cl CH
3I OH5o2ri(an3)2CI Q(3
H, H5o2C1 to 3NHC5°H3H0I to H3 NHCH3CH3HOHOCH3 ”l ”2 ”3 W ’17 ’18
7NHCH3CH3HOHCI NHCH3CH3B OHNo2 NHCH3CH3HOHCO2C02 CH3NHCH3CQ H5o2N(CH,)2NH
CH, °H3HOH5o2C, H3CH(OCH3)2
CH3HCHC)13CI(OCH3)2CH3)]
CH0CH3Cn(oca3)2CH3HOM
CICH(OCH3)2 °H3HOHNo2CH(
OCH3)2C)13HOHCo2CH5CII(OC
H5)2CH3HOH502N(CH3)2CH(OC
H3) 2CH3HOHSO2 (m. 7 CI Cl3HOH-CH3 -〇C square〇]CH,HOH(X:B3 -〇O CH'1CH3)1 0 H(:1 ゝO 0 CH〕CH3HOHNo2 \0 "l F'2 "3 'm] 117
'L6 m, p, (0,) Table 5 HG2H51i 0HC02CH3 H=-C3H7HOHcC'2C2H50H3C2H5
H(rHBrey, 3C2)15HO, u'Co2CM(CH3
)2C)13CH2CH(C)13)2HOHCo,C
)! . CH3°2H5' HOf(No2CH3°2H5
HOHH CH,C2H3H,SRCl CH3C2H5HOH' C2CH3C2H5
CH3'OHCo2CH2CH''CH2CH3C2H
3HOHC02H2CH2ClCH3C2H, CI(
301(Co2CI(3C113C2H5CH3011
So2°H3C2H5°1' 3CH30H802CH
3C2H5CH3CH30HO°H3 CH3C2H5CH30H5o2N(ca3)2R1”
2 “3 Bas”17 “18 m, p
JoC,)CH3°2H5I]5HN02 CH3￥5)1 0 I 5O2N(CH3)O
CH3C2If5CH3H8SC゛2CIi3C2H5
'CH, HC5-F 5o2CI. 021 (50H, HO4-F Br 0H3C2H5HC5-C1Br CB5C2H, HC5-CH5CI C2H5C2H5HHBr C2H3C2H5HOHCO2CH3 C2H5°2H5HGHsO2°H3 (:2H5C2H5HOH5o2N(co3)c2 H5
CH3C2H5HOH5o2((:B2)2CH3C2
H, Cl5HOl(5(J13 C2H5C2H5°H3° H502C1+3C2H5
°2H5CH30HCo2CH3C2H5C2H3HO
HH CH3C2115,HO5-F H CH3C2H3HO5-CI H CH3C215HOH5o2N(CH3)2C2H5°
2H5HS HBr CH3C, JI5HOHF "l R2"3 pz short 202H5C2H
5HOHF SCH, CH3CH30HBr 5CH3CH3HO4-CI Er 5CH3CH3H○5-0CH3H 8CH3(Af, HO5-CI Cl5C
H3CH3HOHNo2 SCH30H3,HC)5-F H ”l '2 ”3 vi ”17 R1
8-metal: CH3CH3H (:, 4-Br If
SCH3CH3)1 0 5-Br Hb0H3"
CH3°H3・ :'02°H55C1130M
3 CH3v HC02CH3SCH3C
H3el! 50 HSt, 2N(CH3)2QCH
3CH, it y H (JC2H. 5CH3CH3ki :HH 5CH3CH3HQ HCo2(CH2)3CH3S
CH3°H3110HCo2°R2°H2°CH3SC
H36H3] (p 5-CI H3CH30H3I
CI HOCII (CH3) C2H5SC11
3CM31i 0 5-CH5CH3SCH3CH
3B CH5CH3 SCH3CH3HQ H5(CH2)3CH3SCH
3°2H5HOH802C2H5SCH3CH3HOH
Go2CI(CH3)2ScH30H3HOHCC2C
H2CH=CH25Ch3 °2H5HCHCo2
°H3SCH3°2H5H:, HBr SCH3°2H5HOS02°H3 5CH3C2H5HS , HCL lj shi 5 Niyōshi Lome aim SCH3C
2H, Hv HNo2SC211>CH3II
OHGo2CIICCIi3>2SC21i,
°H3H (, HC13s02H56H3110H
C02°H3J02115 °H3HOHC
o2°H3Sc2)15CH3;! OHBr5C
2H, °H3CH30H0I SC2H5°H3HS HBr 5CH(CH3)2CAi3HOHCo2CH35(C
H2)3CH3CH3H(H5o2CH3SCH2CH
″CH2CH3HOHC02CH3S(C112)2C
H3CH3HOHCo2CH35CH2C(CH3)=
CH2CH3Ht・HCO2C2H55(1(2C″
cCH3CH3H:'l HCC, 2°H3SCH2
c02CH3CH3HOHNO2SCH2C02(CH
2) 3CH3cH3HOHCo2CH3SCH(OH3
)Co2CH3CH3HOHCCo2CH30CH3°H
3H0HCO2°H3 0CH3CH3HOH button 7CCH3) C2H. 0CH3CH3+1 CHBr 0CR3CH3HOHC1 --b Earthwork 5 Ukura) OCR36H3)! +-' HNo20CH3
CH3H3H5o2CH3 0cH3CH3CH3"', HCo2:H3oco
3 °H3H,, T I (5o20H30CH3
CH3HOH502(CH2)2CH3OCR3C11
3HOHOCR. oC2H5Cd3h, c H(J(CI+2)
3Ca3QC2H5CH3HOHCo2CH2CH″C
H200H3CB3HQ H(X)2CH2CH2C
IOCH3C2H, HOHCC2C1((CH3)2Q
CH3, C2H3HQ HCo2((:I・2)2C
H30C2H5CH3HGH092C2H. 0CI(3(:2H5°H30HC02CH3CICH
3°2H5'H! I1. HCIQC, 756H3H
-J HBr 00H3°2H5HOH5O2CH3 0CH3C2H5HOH5o2(f;R2)3CH30
CH3C2H,H,OH5o2c1(2c)l(c)[
3) 2oCH3C2H5CH3oH8O2°11°0°
KOH3C2H5CM30 5-CI 5o2CH30C
H3G2115CH305-Br So2CH3--U
~'i "17 R184" Yu)□□□憚0C113z2H,++ OHQC2H50CH3
C2H5) i 0 II FOCH3C2H
5It C5-F FOCR3C2H5Hr-H
4C2H5 QC,, R5 open 3HOH5o2N (OCH3) CH3S
C2H5(CH3HOI(502N(CH3)[(CH
2)2CH3]QC2H5C)[,HS HH oc2H5Ch3HS HNo2 QC2H5C)i30 OHC02CH(CH3)
20C2H5CH3F, a HCo2CH2C
H”CH20C:2H,CH3I OHCo2CH
2Cl12CIQC2H50H3H・jHGH3 QC2H5CH3II Q HcH(cH3)2
11JL2H5CH3HO11CH2CH(CH3)2
0C, 2J (5CH3CH3° 11 CH30C
2H5°H3CI-13° H3O2CH30C15ε
H3CI・3o u Ca1OC2H5+:H3H
OH′; 2H. 0C2H5CH3HOHN02 CC2H5CH3+i 0 4-Br BrQC,
, I (5CH3I O++-CI C16155 colors
Hasshi complete set QC2H, °2H51 (CIi CIQC,, H, C
2H,h, -HCo2CH3″2H,C2H,H
OHSo2°H3 oc21I5C,H,Is (: HSo,,N(C
H3) 2QC2H5C2H5H, If No20°2
H5C2H5HOHBr 0C2H5C2115HOHCC2CH(CH3)20
CH3C2H, HU H! :, 02C2H. 0CR3,C2H,l” 0 4-F FQC2H,
0M3HOH0CH(OH3)20CH2CI=CH2
C113110H802CI3ca2c(Ca3)<H
2CH3+(: H-sword 2CH30 to l1(CH3)
Cl5 town HOHC02CH30tl;H(CH3)
2CH5HOHCCo2C2H3C(CH2)2c)i3
CH3HOHCIOCR2G! ICCH3CH3HOH
N02CH20CH3CH3Ho HBr CH20 Town 0H3II tr HCLOi2
0C1 (3°ll30h30 II C,020H
,. 0M20Ck13CH3C1i30 )I C02
C02CH3CH20CB3COHC02°chiRIR2
R3 Bass to 5 5th ward summer c1 (2°CH3°H3H,,,HNO2':1i20
CH3CH,li S HC1']H2SCH3c
143 HOl“H:H20
CH3CH3HOH5o2N(CH3)2(:H,,Q
CH3CH3 Town OHSO3M (Cl3) C2H5Q12
OCR3￥, HQ H5o2C2H5CH20
CH3°2H5”J HCo2CH3C1 (2°c2
H5, CH3I CHBr0H20cH(CH3)2
CH3Ho HCC02C. (λ20(CH2)3CH3CH3HOHC02CH3
C12CH20CH3CH3HOHC112an2oc
H(CH3)2CH3HOHCo2CII3N(CH3
)20H3HC) HCo2CM3CF3
°H3HOH5o2CH3OF3CI3HC,H,Co
2CH5 CF3C2H5HOHcO2CH(CH3)2CF3
62H,H(l HE, 02°H3CF3C2
H, HL゛HBr CF2°F3 °H3HOHC (2°H3CF2
CF3CH3,HQ HCl CH3CH20CH3HOHCo2CH5R R2
5i汫し - 区匝CH3CH25CH3H"l' HtelCH3C1
2CH20CR3HOHω2°H3CM3CH2CH2
SCH311° ++ BrCH20CR3C2H5
HOHCC2C) 13CH2°C113c1(3°H3
° I C002°H3OC2H3CH,0M30
H5o2(C12)2CH3QC2)i5C
)13 HO! lS
・2(ii(C:Iiu)2QC2H5CH3H(・
u 5O2N(';2H5)20CH3°H3H+;
HCH3 0CH3, CH3I OHC, R5 0CH3an3HCH0H (el+3)2ccH3CH
3HOHOCH2CM2°H30c)13°H3
HOHF OCH3CH3HOHGO2C2H5 0CH3CM3H (02CH to J H, H2QG to JH)
! 30CH3CH3lI '-' HC02C
H2C11"CH2CH2O0H3COHSo,,N(
C113)20CH30H3HOH5o2tJ(ocH
3) an30CH3 town H (F HSC,,CH
2CH″0I2QC2H5C13’HOHF OC2H5°113II OHC1 kl R2R3W RA
c2H5CH3HOd Br 0C2H CH3I・Oi('C02CH3Q
¥, cH3it OH5O2N(CH3)2QC
2H5CH3F, OH5o2CH3QC2H5CH
3HOH502C:1I2CH=CH2(X;H3CH
2CF3HOHCH3 0CH3CH2CF3HOHH3 OCH3CH2CF3HOHC1 oCH3CH2CF3HOHNO+2 ocH3CH2CF31i 0 HCo, CH2C
H30CH3CH2CF3HOH5(12N(CH3)
2QCH3CH2CF3II OHS020M3C
I CH3HOHCH3 Cl CH372HOCH3 1 C1, CH3'HOHCl ClCH3HOHN○2 CI CH3101(Co20H3C
I 0M3HCH5c2N(CH3)2CI
CH3Hv H1%20H3N
H3HG HCH3 rJl to HCi13 (CH3CH3HOHOCH3 ”l ”2 ”3 !i”17 Hase Goe
d) NHCH3CH3H' OH:1 NHCH3CH3HOHNo2 NHCH3CH3Ha II Ct'2°■"5N
HCH3CH3HO145o2N(':Hρ2NH(1
;H3CI3HG HSo2°H5CH(CCH3)
2GM3HOHC13C1l (CCH3)20H3HO
B 0CH3CH((JCH3)2CH,HOHCI
CH(OCH3)2- 0H3HOa No2GM(
OCH3)2CH3H(> HCo2CH5CH(C
CH3)2CH31+ 0 11 5c2N(CH3
)2an(ocu3)2CH3HQ H5(12CH
3, H0] 5,. □. □.ゝO CI″JC113HUH 5%0 GH) CH,, HOHC1 ゝOC,;') CH, HO! No2\0 ``l ''2 ``3 r・, '''1
7 R18m, 1 ku 匝] -201- Ta 6 5 (3 [(IR2R3 and 5 '00 Hat C, H5HQ HCo2Cl5J B
-C3H71! Oi(C02C15:H3C2H5
! (:J HBr 13 °2H, HOHCo2CH(';)i3)2
11:H3CM2CH(C113)2HOHco2aH
3shiH3C2H5HOHN02 0H3C2H5HOHH CH3°2H5H8HC; l CH3°2H5r+ On Cl CH3C2H5C130HCa2C112CH=CH2
CH3, C, 2H5HOL (C゛L2C・1I2CH2
CICH3C2H5 3° H0″・, qH. CH362H5°) 13° H5C2CH3C2H5C
H3CH3° HSt:2CH302H,0H3CB3
0 ) 1 0CH. CH3C2H5C13G HSo2N(CH3)2A
R2i″3 V+ R17″18 m,
1〆Aim CH3°2H,il S)I No
2C113°2H5HOHso,,r+(C+;3)o
cn3C2H, CH31+ S 14 St,
;2Ci(3C2H5(';++3HO5-F 5o
2CH3C,, H5CH3HO2-F BrCH3
c2a, ++ C″”)-CIBrCH3C2
H5H(15-CH5CI C2H5C2H5+1 1; HBrC2H5°2
H5I+ ,, 112CH3C2H5°
2H5](('HS・'2CH3C2H5C2H5
H(・H8o2N(CH3)c2H5CB3C2H5H
・-5i-2(CH2)2CH3C2H3CH3H・
SCH3 C2H5C2115CH30H, 5tJ2CH3C2H
5”2H5CH30h C02C)1302H5
, ¥5HOHH CH302H5Ht, 5-F HC
H3C2H, HO5-CI H C2H5C, H5II CH5o2N (C113)
202H502H5HS Br C) i3C2H5HOHF RIR2R, Vi
H3)2CH3HOHSo2CH3CH2CH(CH3
)2CH,II ,)HCo2C2H5°CH3=-
C3H7HOHBr CH3CH2CH=CH2HOH 2CH(CH3)2
CH30H2C (CH3) duck H2HOHω2CH3CH
2CH″CH2 town li OHC2H. CH2C(CH3)=CH2CH3I OIf
502CH3CH3°H2°”CCH3S OHC0
2°H3CH2C″CCH3CH3HCH5o2C2H
5SCH3CH3HSHBr SCH3°H3CH30HBr 5CH3CH3HO2-CI Br 5GI3CH3HO5-0CH3H SCH3,CH3S 5CH3CH3 of 05-C1, HOHNo2 SCH3CH3HOH802N(CH3)C2H5SC
H3CH3HOa 5o2tJ(CH3)(ca(CH
3)2)S43 CH3HOHF SCH3CM3H05-F H “l”2 R3W R17R187SCH3
CH3HO2-Br H CH3C23H(, 5-Br H SCH3CH3CH30I 5O2CH3SCH3
CH3CH3' OHCo2CH35CH3(:H3C
H,OH5o2N(CH3)28°H3°H3H
HQC,, H5SCH3CH3HS HH 80H3cH3HCHC02(CH2)3CH3SCH
3CH3HOHcO2CH2CH20CH3SCH3C
H3H, C,5-C111 SCH3' CB3+1 v H0CR(CH3
)C2H5SCH3CH3H05″″CH3CH35C
HCH3S Q HSCH35CH3CH3HQ
HS(CH2)3CM3SCH3C2)15HOI
ll 5o2a2n. ,5CH3CH3HOHCo2CH(CH3)2SCH
3CH3HOHGo2CH2CH=CH2SCH3C2
H, Hv HCo2CH3SCH3°2H5HOHB
r 5CH3C2H, HC, HSo, CH3SCH3°2H
5H3HCI FlIR2R3 Blue ``17'' 18 Ji-style box S
CH3°2H5Ha HN02SC2H5CI3
Hc n co2cu(:H3)2SC2H5CH
3HCHCH3 5C2H5CH3H0HC02CH3 3C2H5°H3HLj HSC2°H3SC2H5
cH3H○ HBr −)C2H5°H3CH3° HCl 502H5°H3HS HBr 5CB(43)2CH3HOHC02CH3S(CI(
2) 3CH3CH3HoH502cH3SCH2CH-
CH2CH3S OHCO2CH3S(12)2CH
3CH3HOHC02CH3SCH2C(CH3)=C
H2CH3HOHCCo2C2H3f; C112C″CC
H3' CH3S OHC:2CH3ScH2C
O2CH3CH3HOHN02SCH2Co2(CH2
)3CI3CI(3HOH,,Co2CH3SCH(C
Co2CH35CH(C,HOHCO2CH3,0CH
3CH3HOHCo2CH3 0CH3c)i3Hc, H5o2N<CH3>c2
H. OCH3CH3HOHBr OCH343 HQHCI Town R2R3W R1? R18? i,? , (0
C) OCH3°H3HOHNo2 0°H3CH3HS H5o2CH30CH3CH3
°H30HSo2°H3OCH3°1 (31+L
, H5C2CH30CH3 to H3Hv H5o2
(C12)2CH30CH3CH31i t・H
0CH3QC2H5C1;3 HL n
a(Co2)3cH3QC2H5'CH3
H'HCo2CH2CH<H20CH3CH3H
OHCO2CH2CH2CIOCH3C2H5HOHC
o2cH(Co3)2oCH3C2H5HOn C
o2(CH2)2CH3QC2H, CH3I OH
Co2(,;150cH3C2H5CH30HC02C
H30cH302H5HS HC1 oC2H5C2HS HBr 0CH3C2H5HOH5o2CH3 0cH3C2H5HOH802(CH2)3CH30C
H3C2H5H4・H802CH2CH(CH3)20
CH3C2H5CI, OH5O2CH300H3G
,,H5CH305-C180,,CH30CH3C2
H5CH305-Br S02°H3”l ”2
"3-W"17 '18 ni
,p,(0;;)ULH3°2H,HG HQC
2H50CH302H5I! (・HF<+CH
3C2H3H'O>-F FOCH3°2H5H,)
)i S:E2H. QC2H, CH3rr L H502
N (trial a3) cH30C2H5CH3HOH8o2N (
・TSH3) [(OH2)2cH3]OC2H5 hit 3H
3H'H QC2H5CH3HS HN02 c1C2H5CH3HOHNo20H(OH3)2QC
2H5CH3HOHCC2CH2CH″CH2QC2H
5CH3HOHCo2CH2CH2Cl0C2H5CH
3He kl cll. QC2H50H3HcHCI(((:R3)2QC2H
,CH3II OH0M2CH(Cl3)2Q°2H
5CH3' CH30H0M30°2H5013”C
H30H5o2CH3QC2H, CH3CH30HCI QC2H, CH3I tHC2H5QC2H5CH
3HOHNo2 QC2H5CH3HQ 2-Br BrQC2H5
CB3II C,, 2-CI C1"l
“2”3 W “17”18
m, p, (0r,)Oc21(5°2H5'HL,
HC1oC2H5C2H,)i 11 C
020H3QC2115C,H,H(, H5o2Cl. oc2n, C2H>Hr= H5o2N(
Cl3),. 0C2115C2H5HOHNO2 QC2II, C2H,HQ HBrOC2
2H5HOGo20H(C;R3)20CH3 to H5
C2H5II OHSo2°2H50CH3°2”
5 HC2-F FQC,, II, CH3
)1 0 H0CR(CH3)20CH2':1peH
2C1(3H(-H502CH30CH2C(C1!3
)-CH2(:R3H' fuh HGo2CH.ocn(CH3)cノ15CH3HOHCo2CH30
CII(CII3)2CH3HOHC02C2H5o(
Co2)2cH3CH3Hv HclOCH2C Town C
H3CH3HLi I(No2CH,, CCR3CH
3I OHBrCF20F3 to H3HU HCI ClCH20CH3C°H30H5o2CH3CI20
CI3CH3CH30HCO2CH3CH2°CH3°
H3HG HC02CH3RI IO2
R3~l'r! 17 R18m, pJ04:)Co2C
R30CII′-“HNo2′:l!20CH3C
H3HS H to 1- CH2CH3C:H3HOHH CH20CH3CH3h :Hi)02N(':H3
)2CH2QCH3CH3CH3L: HS('2N(
';H3)C2H3OM2;-CIO3C2H5HOH
502G,)I5CH2°CH3°2H5' HOHC
l>2CH3CH2QC2H5CH3HOHBr CH20CH(CH3)2CH3Ht, a Co2C
M3CH2Q(CH2)3CH3CH3HOH flash 2CH
3CH2GH20CH3CM3h v HCICH2
Cl+20CH(OH3)2CM3Hu HCC2CH
. N(Cl3)2CH3HOHCo2CM3CF3CH3
If OHSt2°H3CF3CH3H(, I C
02cH3CF3 C2H,
Hc HCo2Cl1(Cl3)2CF3
°2H, HCH5o2CH3CF3 °
2H51(tiHBrCF20F3 °H3H
OHCO2°H3CF2CF3 °H3HOH
CICH3CH20CH3HOHC○2CH31 cell
k2 ”3 5.R17'18 Yu food
) CH3°+123 H3HOHCI C:R3C112CH2(X:H3HQ HGo20
H3CH3CH2CH2SCH31+ v HB
rC1120CH3j, :2H51i 0 H■2
CH3C1+20CH3CH3CH30HC02CH3
QC2H5C)13C1130115o2(n2)2c
a3QC2H5CH3II OH502cH(CH3
)20W5 °ll3HOl(so,,ry(C,?n
5) 20CH3CI311 0 HCH3 0CR3CH3HOH ¥5 CCH3CH3110HCM (CH3),. Sound3CH3HOCH2CH2CH3 0CH3CM311 Q HF QCH3CH3HOHCC;2C2)! . 0CH3cH3H(,HCO2°H2C1120CH3
0CH30H3II OHC020H2011″CH
2ocn3cH3,II OHso,z(CR3)2
0CH3CH3HOH5o2N(OCH3)CH30C
H3CH3H(t 11 5o2CH2CH='CH
2oC2H,CH3I OHF QC2H5CH3HOHC1 ”l R2R3W ”17 '18 7
)oC2H,CR3)1 t+ HBrO°2H5
°H3b CHco2°H3□□□2H5CH3HC
HS(・21shi(CR3)20C2H>0H3)i
(, H5O2CH3QC2H, CH3I :i H
5O2CH,, t:l1=C)+20CH3C'r',
2CF3ii Q HCH30cH3°H2°F3
H1, H0CH30CH3CH2CF, HoHCl 0CH3CH2CF3HOHNo2 0CH3CH2CF3HOHCO2°l (2°H30C
H3CIL2CF3HOHsO2N(CH3)2OCR
3CH2CF3' I OI SO2''H3C
I CH3I OHCH3 Cl CH3I 011 0CH3CI
CH3I OH'Jr20H3CI CH31
5,, H5o2N(C)! 3) 2CI 0H3It
v H5o2CH3flcH3°H3110HC
H3 NHCH3CH3HOH0CH3 11shi 5stand 5shimu t+H':113CI3H° II CINH°H3
CH3)i:, HNo2NHCH,C
H3I H'C02CH. NHCl13CH3HG H5o2N((:R3)2
NHCH3CH3HOH5o2C13 an(t,co3)2CH,HOHC115aH(oc
t+3)2CH3Hc HQdiCH(HCl3)2C
H3HOHCI CH((,CH3)2CH3HCHNo2CH(IJc
)13)2CH3HQ H502C1l. CHI CH3I OHNo2 0 RI I (2R3~・-”17) lxts
=I50 CH1CH3I Q HCt-:2CII3%()
, - 0 CH'JCH3HI) l(E, t, 2NCCH3>
2\0 0 CH -〇Croat 7 1ゝ3 klI"2 5 2)ヱ) Upper Melting point) ---
-Inquiry■-- 11 Knee C3H7HCHCo2C) I3cly,
CH(CH3)2HOHCo2cH(Cn3)20
H3CH31I Q HCo2) 12Cii″CH
2nd-C4H9! ;H3HOHCl CH20H<HCH30M3HOHBrCH2CICC
H3CH3110HCH35CH, CH31i OH
Co2CH(CH5)C2H5SI:H8CH3CH3
CH3HOH(:1:;(CH2)3an3C113H
OHBr5CH (i:1(3)2.CH3110H
Co2C2H55rH3CH3CH3°HCH3 5CH2C! :, cH, CH3I OHC;02Cchi
8Cit2Co2an(0%)20H3H(>Hal
SCH(0M3)Co2C2H5C13HON5rN(
CH3)2CH, Ho H, Co2CH2CH2CH3
CF3C2H5°H3°HH 'l ”2 ”3 V, ”1
7 “18 r, l+” io:)! New] F29F3 CH3i (S
)! Go2':H2C1i2CIO':2H
5°H3HSH(:H3 aCH2cH(an3)2CH3HCo, :1CH3C
H20CH3C)i3C1;3CHC:2riH2CD2
0eH. CH20C]l(CH3)2CH5H(HC(12riH
(Ct+3)2CH20'H3CH3h S h
'tsu1CH,CH,:H2OCH3・10)i 'ko
1CH3C1i2SCH3HO)i BrCH3Cl
12(<H3HOHCo2CH2CI(C1i3)2C
H3, (1(2CH2S(H5H(: l! (X,
CH3 SCH3n-C,kL, HSHCH2CH3CH
2CH(CH3)2HOI(CH3C2H3H3HQ
HCt・2CH30Q:3' CH3CH30HCl 0CH3C2H5HOHCo2CH3 ゛2115 CH3HS 11
Br5c) 13CH3Han Co2Ca3
CH20CH2C12CH3CH3+1 08 CH
2CH3C)H2C(CH3)=CH2HOHCIQC
2M, °H3°H3S HCH3QC,,H5
G3, HOH■2CH(CH3)21<1k2I
“3 □'1?”18! Jroyu) 5112″
''H3C1i, Hv HC
o2CH20H"CH25C2II, C;H
3II OHCo2C2H5CF20F3 0
13 kt (・h Co2CH3cho3(;
2H5HOHCO2CH3! :H, CH2H=CH2HOHC02CH3G! 3
, C)・20″ICCH3II θh
CH3SCh3)i3CIO30H902CH(OH
3) 2SCH,0H3HOHH 8CH3CH3CH3(・H11 SCH(4':H3)Go2CH3C2H,,,H50
2CH35GH3,C2H,fjHCo2CH,-CH
2CH20CI(・;H3)2CH3HOHCISH
3CI+31+ OHH OcH2C4 (<ll2CH3HCH Kasumi2C2H. uCH3' HBr0H2CH to C2H5H
2°CH3CH,HOHC02°H3bCH2";Q1
0. ,H,C)I3HQ H9020M3(,C12(
:'ICHCH3I OH0M3uc2H5C113
CM3°HCar2CH3oc2iI5s>:3H'-
HCo2CH2CH″CH2QC2H5CH3!:
O! T Co2CH2CH20CI'13-
5 fireworks noise discharge) t C2115CH,h HC,-'2CH(+
:) i3) C2H5CG21150H3: :'
HBrQt;2H,CH,l('OH,:10C2
H5CH3i(°・1(l) ○C2h5 cH3h o u C02(c
ri2)3CH3SC113'C113110H'0
2”'2C11'α2-)CH3CH3, ki 0H
“2c2H5SC113°ll3H(i HCH3S
H3CH3kI CHC02(C112)2C13
SC) 13CH3HOHBr 5CII3CH3II OHCl 5CH30H3C1 (30HCl 5CH3CI3CH3C' HBr 5CH3CH30H30HCC2CH5E, C113G
,,H,11':, HCH3E, CH3C2H3H
CHCo2C2H55CH3C2H5II
Br0CR3C2H5HC: HCo2(CH2)
3CM30CH3(:2H5, HC4-Br HOC
R3C2H5HO4-Br C02CH30CH3C
2H5HO5-CI Co2CH (3 towns k2
R3, No. R171ゞ18 Three-way CCH
3°n2H5HO4-CI C02 gates 0 gates C
2111,++04-・;l Natsume 3 C02CH3
0CH3C2H5If OHC02G)! ,':il
″Ck120CH3C2H u
G Hco2c+r<cH3)2tX:H3CH
3HOHH CH3Cu2a OHCl 0CH3CH3+1 0 HBr 0CH3CH3HOHCH3 0CH3CH3HOGo2CH3 0CH3CH3) 1 0 HCo2C2H. 0CR3CH3n (Hco2co(CH3)2
00H3°H31i i-HGo2Ci(2CH2C
H30CH3CH3fi OHCo2(CH2)3C
H30CH3CH3HOHCQ2CH2CH20cH3
0CH3aH3HOHC02CH2CH2CIOCH3
CH3HOH'Co20H2CH''CH2O°H
3°H2°F3 HOHH OCH3C)12CF3II v HCl0CR3
CH2OF31 (OH, CH30) 0H2°F3
F, 1-Co2CH30CH3Cri2CF3HO
HCo20H2CH″CH2RIR2R,,,R17R
185 ゝvCH30H2CF3H112'-, C112CH2G
ICI CH3Hi HClCl
Cl5HL H, C113CI C113
)i 0 HS('2ell. CI CH3HOHC(]2e
H2C1l CH2NHCH3Cl5HOHBr NHCH3Cl3HOHCo2°2115NHCH3°
H3i1 0 HCo2CH2Cl12 to ICH (H
CH3)2CH3) ■0HCO2CH383 RIR2R, ViR,, R17 Melting point (6) H, n-C3
H7H0CH3)i HC2H3H,0C2H5H CH30H(CH3)2HOCH3H CH3(:H3Hs cu(cH3), Hnee C4
H9CH5H0CH3H CH2CH=″S12CH3■IO°H3, HCl12
°(CH3)=CH2CH3HO0H3HCI12C=
CCH3CH3HOCl3HS, CH2CH″CH2C
H31・O'2H5Hsch2c++ to H3)2'
Cl3HOCH, H5CH2C''''CHC)+31
i 0 Cl3H3C2H5=H3HOCn(cu3
)c2u5t+5C113CH3°)+30 CH2C
H2Cl H8CH2Ca2C2H3CH3HI-C
2H,HN(CH3)20H3)1 0CH3H total”3
C2H, +1 v CH2CH206H3HRI
R2R3. r 1″9 R17<”,
:) CF2°F3CH3F 0n-C3H7IIQC
2II5CH3”:H3ΦCM(CH3)C2H5)!
0CH2CH(CH3)2CH3・i 0 CH3'
・0CH(CH3)2 CH3do ○ C2
H5HCH20CH3Il□3
S CH31rCH3C1i2':)i2°)C
)i3HO(143HCB3C)i2SCH3HO°H
3, HCH3qn2oCn3HOcH to u3)2HCH
3°H2°H2SGH, ii O0H3H5CH3r
2-C3H71i 0CH,HCH3Cu2a(Cu
3) 2HOan3HQC2H5CH31i 0 Cl
3HO°H3CH3CH30Cl3H OCH3C2H,H0CH35-CI OCH3C2H5HO0i135-BrCH3CH2C
H<H21i 0 Cl3HCH3CH2CH″CI
ICH3HOCR3HCH3CH2C:CCl3HOc
H3HQC2H5CH3I CI CH34-CIO
CR3, C2H511ClCH2°H2CI HC
2H5CM3HS CH2:H20°H3H"l,
“2”3 vt l(9”17 7)SCH
3C1i3HQ CH(CH3)(:2H5HCF3C
2H5Ht, CH2Cl-CH2Hco2ah2oc
2n, CH3I Q CH(CH3)2HC1
120-a(2C)l(C)! 3>2cH3HO￥54
-CH30C113C2) 15C1130 knee C4H9
H8CH3Cl3CI30 knee C3H7HCH20CH
3°H3':l13C7CH3H゛CH20CR3CI
3I OC2H3HCF2CF3 to 21i511 0
0H3Hocn3C2H,)l S o+(CH3)
:2H5HO°H3G,,H5)! S 0H35-
ocu3scJ13' CH3HS 0H3I 5 weeks-
03) 17CH3HOCH311QC2H, C, H, H
OC23H OH2C sound C2H, HOCH3HCH3C2H3
HOC1(CH5)2H5CH3', CH,I
I O Me 031 (7HOCH2(:H=CH2CH
3H0CH3HSCH3' 0H3II OC
H3HSL+1・30H3)i rrc2H5H5C
H3C2H51i 0 CH3ISCH3C2H5H
L) C2H5+1SCH3CI3Hv CH2C
H″CH2H8CH3CH3)1 0 CH2(CH
3) 2H3CH30H3CH3SCH3H 5CH3cH3HS C2H3H QC2H,0M3HOCH35-F OC2H5CH3' HOC2HQ 5-CIQ
C2H, CH3I, -OCH35-Br0C2H5cH
3HOCH(CH3)2■lQC,H5CH3HO,C
H34-BrQC2H5CH3HOCH35-CH30
C2H5°H3HS (m3H QC2H5CH3CH30CH3H QC2H5CH3CH30C)i(OH3)2HQC2
H5cH3CH30CH,, CH=CH2HQC2H,
CH3I OB-C4H9HOc2H5CH3HQ
CI(2CH(CH3)2HQC2H5CH3HOH(
:3117HOCH3C2H5HCI CH3I OCH3C2H5HS (1 (3H OCH3C2H, HOCH34-F "I R2" 3 and 5 〒 Tailoring) OCH3
C2H5HOCH35-F OCH3C2H5CH30CH3, H O(:H3C2H5CH,',)C12CH”CH2H
OCH3CH3Hc CH,H OCR3CM3HOCH(CH3)2H(JCH3,C
H3I OC2H3HO°113 °H31!
OCH2Cl2cH3HO°H3°H3HO°H2C
H<H2HOCH3CH3HOCH2 to H20CH3H
times, CH, HOCH2Cl2CL HO°2
H5°H3H00M3. HOCR3CH2CF3
HOCH3H OCR3CH2CF3H002H, H ocu3CH2CF311 0 CH(CH3)2HO
CH3CH2CF3HOCH2CH=CH2HOCH3
CH2CF3HOCH2°H20CH3HGCH3'
0H2CF3HOCH2Cl2CL HCI
CH3' HOCR. CI 0M3HQC2H5H CI CH3' HOCH2CH=CH2HN
H(1:)13CH3HOCH3H R1% R3, +(9shi Oxni motherNHCH3CM3HOCH2Cl2CL HNHC
H3°H3HQ CH2°H20CM3HIOICH
3CH3110C2H3H OH (OCR3)2CH3HOCH2 Cl2 (OCR3)2 CH3 Summer (OCR1
(5'HCH(CCH3)2C1!II(CH(CH3)
)2H0I(OCH3)2 CH3HOCH2CH
=CH2HCH (Kan H3) 2 town HOCH2CH
2C1,H,0 0ζ. , 7 CH3I O°H3HCH']
CH311'OCH2Cl2CH3IO 翫O 0 0H) CH3I OC)T2(:H20CH3H
\0 0 CH,] C13HC, Cll2CH2CL H
ゝ0 0 begging 2 11 t3)ll "2 R3WR9"17d--
暉■－■－－－－■－－■■■－H knee C3H7'I
(OCH3H CH3°2H5HO°2H5H CH3CH(CH3)2HOC3H 7C30C)! 3)j QC)I, HH-C
4H9°H3HOCH3H CM2CH=CH20M311 00H3Hc)12C
1((CH3)<H2CH3HOCH3HCH2C=O
CR3CI3I O0M3H8C)12CH=CH2
CH3HO(m3HCH(C1i3)C2H5C)[3
HOCH3H8CH2(CH3)2HO Town H CH3 SCH2(JCHC13H0CH3H 5C2H, cll, H(M1m3H8CH3CH
3CH30CH3H 3CH2Co2CD(CH3)2CI3HOCR3HN
(CH3)2C13H0CH3H SCH3CH3CH30CH3' H5CH3C
B3HS C2H,H 8CI(3CH3(,CHCCII,)Ch)l5
CH30kI31"0°H2°H2"H3H8CH3
C2H,HOC)i((:B3)2HCF3C2H5H
O°H2CH=CH2HCF2CF3 °H3
1i”S CH311QC2H,CI(,ri 0r
4-C,H7HOCR2CH(CH3)2CB3HOC
3H7CR(OH3)2CH3II S CH3,H
CH20CH3OH3Ha CH,,cH2CI H
8CH2Co2CH5CH3HOC3H7CH (0M3
)CC2C2H5CH3HOCH3HCM3CH2CM
20CI3HOCH3HCH3CH25CH3HOCH
(CH,)2HCF3CH20CH, HS C2H. CH20CR(OH3)2CH3HOC13HcH2C
I(2oc2H5CH3HOcH3H8CH3r4-C
3H7CH30C3H7C2H, CM3CB58 Cl
5H oCH3cH3CH30CH3H R1-35☆89 5 Humiliation 匝0CH3C1i3' ii c, CH3'')-C
10CH3C,k15HO'CH32-Br0CH3C
2H5HS C3H 7H5ji 1 (○CH35″″CH3cH3CH2
CH"CH2I Q n-C3H7HC)130H2
CI((CH3)2HOCH(CH3)2HCH3CH
2C! c-CH3I OCH, HoC2H3CH3C
1130C2H, HCF3 62H5H8CH3
H ocH2°H=CH2C)13HOCR3HOcH2C
″cHCH3H(′CH3H5cH3C113HOCH
2C3(20CR3HSCH3CH31i 0 CH
=CH2CL HCF2CF3CH3CH, CC3H 7CB30. B5 %30 town HOCR3C
2H5) 1 0 CH2CH=CH2HcH2ocB3
cB5HOCH3H 5CH3CM, H(ICH3H6CH3CI(
3HOCH3H 5CH3CH3H0C2H5H 5CH3°2H5HOCH3H ``l''2 ri3 W, '9
”17 rSCH3C2H5HOc2H,H 8CH30H3140CH2CH=CH2118CH3
cH3i1 u CH2(C:j13)2H5(
:H3CH3Ch3S C3H 7CB3CI(31+ D C2H, HQC2H
5' CH3)i 0 CH35-FOC2H
5CH,HOC2H5u-CIQC2H5CH3HOC
H35-Br QC2H5CH3)i 0 C) I(CH3)2H
QC2H5CH3HOCH32-Br (X:2H5CH,, HOCH35-C113C113
95C5CH3H O(:2H50H3CH30CH31 QC2H5CH3(1(3C,CH(CH3)2Hα;
2H5GH3CH, OCH=CH″CH2,, HQC2
H5CH3HOn-C4H9H OC:2H5CH3)i Q CH20CR(CH
,)2HQC2H5CH,HOnieC,H7H oCH3C2H51i 0 C3H7CI(3C
2H51i S Cki3MQC; H3C2H,
HOCH32-F "R2'3""9 117 m
-p-('C) FilOCH3C21'15H
O"3'-P'NHCl'130CH3C2H
,CH3C,CI3' HTiHCH30CH3
C2H5CH,OCH2CH=CH2HNHCH3%
CH3h (J ”3 HNHQs30
CH3CH3II OCH(CH3)2HC11(0
(HH3)20CH30H3i1 0 C2H,H,
CH(OCH3)20LH3CH3HOCH2CH2C
H3Hr:r(<0cH3)2jiH3C113HOTSukuda2
CH'', CH2HC)ICL)CH3)20CH3CH
3II OCH2CH2CH3H' CI(OCH3
)2 咋) ・m2CF, H+, (':H2CH
2CL Hcl CH2H2CH3H C1,CI(,,I OC2H5H Cl CH3Hi;H2(m=cH2Hshi 5 Standing
5 dagger) CH3HOCH3tl CHI3It ○ C112C112CI I
ICH3HOCI(2CH20CH3H CH3H(□ C2H3II CH3HOCH3H CH3141 C2H5)i CHHOC1i C(:i+3)2H CH3H0CH2CH″CH2H CH3HOCH2CH2Cl H CH3HOCH3H C Di HO0M20H20H3II CI3HOC112C1120CH311CH3H(,
(m2CH2CL H-5 and parrot 5□
y Ward C: H3HS C111 CIi3CH30No2H zli3CH30CI H town)! OF H c2H5HOHH CH3HO Han 2T4 (CH3) 2!1 ¥5HO milk"2°H311 C2H5(':H305o2(C12)C25H02H
5HL' 5o2N(OCH3) HH3 C,H5C130SL,2°2H5H C2H5HCr QSO20H3H C2H,HON02M CHHOCI )1 5 C2H,HO5a2N(ca,)C2H5H02H,H
OH7′″F C2H5HO)I 5-θCH3C2H3H
ONo28-CI CH3HS(:H3H G13HOCL H'j1 ”2 ”3 r't ”1
4 ”15 ('C)C1i2C=CHCH
3I OIJQ2HCH2C kiln CH36H3d O
Br HCI+3':H2C11=(:H
H2 to 2N 00CH3HCI+3
r'(':H3> :kuto+2 I C,+q
o2 HCl13Ch2°5
"Translation 31" to 502°H3HE:Cl13C1,3
C113°H)IS(:HCH3C23F No2H s(':)+3CHzu CH30CI
H5CII3CH3″! ~・HH scii3CH3+4 GNO2H SCH3CH3HOCL Hf, cI(,
CH3II O0CR3H8C positive 13
CH3HOCH3H5 gate CH3HOF
H56II3 Town H5Ii
H5CH3°H3H8CI HE,
CH3CH3I S No2H s':H3°2115'i 00H3H8
CH3,C2H5,CH2ONo2HSCH3G,,H
5CH30HH SCf13C2H5HO0SO2r:HCl2H, JC
H3CH3++ ○:5a2c+“2CI・Band I
fSCH3CH3... OtJi? ,02C1i(';
](,)CH2F 14-J CH3CH3h
= ”-8L2(CH2;3Br h
SCII3CH3Hb C5L2CCH2)2SIIC
12IICH3C2H, HQ 0B02CF,
HCH3C2H3F, 0O8O2CF2CF, 2F
HC2H5C2H5h, 003020M2C
F3H5CH3C2H51i Q! ;5o2CH!
, )70M3C,,+(,HO0S02CCI
3HSC2H5CH3HOoAo2co3H8C2H5
C2H5HONo24-Brsc2n5CH3HS H
,5-acs3SCH3CH3CH30F
7-FS(CH2)2CH3cH3HOCH3+3C
H(CH3)2cH3Hoso2N('1L3)21I
SCH(':H3)C:2H5CH3HOBr
JiSCH,C:HCH3C23F OCI
IISCH2C(CH3)0M2CH3I
Q C111SCH2C! cCH3CH'r, Q
No2IfSCH2CC2CH3cH3HO802C2
H51;5CIi2C02C12CH,CH,II
OCI H”l ”2 ”3
'k R14)'15 (OC)sch(CH3)
cc2Cu3C13); CI Br
H3CH(C113)Go2C2H,C113HOH
H[;H2OCl3 6H3CI30HHCJI
2QC) 13 0H, HS HH
f; H20°H3°H31 (ON02HCH2QC)+
3 °H3d' Q CI
H0H2°CH3C)13HOBr H
C)]20CH3°H3HQOCH3HCHHSH6-
Br 0H20°H33 CH20CH3CI311 S H,'
3″-CIC1!20CH3C2H,H,OF
IIel+20°H3ゞ:113II O
5(J2°285 H(';H20CH3C
hi, li +,) 5G2N(CI+3)2H
9H20CH3 gloss, HOO502°2H, HCH20c
2n5 °H3' HOC, H3HC112QC
2H5' CH3I SHHCH20(CH2)
3CH3CH3HONo2HCH20CH (C113)
2CH3HOCL HCl2HOCH3°
H3110H' Han2cH20Cu(
CH3),, CH3I O0CH3HQCH3°2
H, Hi'J HH 06H3C2H5+1. =' )l
HO°83CH3CM3Q 1i OCI(3CH3CH3(”71
Hocn3 C2H
5++ (: ::, u2N(*n3) p
H(cli)2CHOC)+3C
2H5j ■ o 502N (CH3), gu:H2)
2c1f3] HOCR3C2H, HC5O2N(CH
3) 211ocH3CH,H' CI +, ;5(2(
''H2)2HCl2HOCH3CI(5HO08G
2CH(CH3)′HF2 1:0°H3cH3H00
SO2°HFCF3HQC2H5CH3HOBr
HCH3C23F OC14-CI QC,, H5CH3)i 0 H8-No20C2H
5°H3HSHH QC2H, CH3I A No2H QC, J, CH3I G 5CH3HO°
2H,CH3I OSCH,,CH(CH3)2HQ
C2H5CH3)1 05(CH2)3CB3HOCH
3C2H5HO5(C112)2CB3IOCR3C2
H5HCSC2H5H OcI(3C2H5Hoso2cH2cH(CH3)2
HOcH3C2H5Hoso2cH(CH3)2H”l
R2R3W “14”15
('C) - 1111 - 4 upper knee
-CCH, °2H5HO5c2cH3H oCH3C2H5; + o'2("H2)2CH3
HFノ(Cn2)2co3 C), 3 +i
u 5O2N(CH3)2 Hocn
(・shi113)2 CH3□j OCH3HOC
H(C113)C2H, elf3Ii Q 0CR
3HOCH2CH=CH2CI3HOHH OCH2CCCE3>=C112C113I OCL
HO°H2C'CcH3°113i(ON
02HN(Cn3)2 CI, );
O)ζ 1IN(C1+3
)2CH3110CI HCF3CH3++
'OCI HCF3CH3n o n
○2H CF3CH3HS ′:l HCF3C2
H5HOII HCF3C2H5HOF
H F 3C2H5HO8o2CH(CH3)2HcF3C2H
5HO°5O2c21■5° HCF3C2H5HO
0502CH(OH3)2HCF2°F3 8H
3I OO802CM3HF CF 23CH3HU 0802CH2CH2CL Hc
F2CF30H3110N02H CF2CF3C2H5'r; OC1110H3CH
20C113F Br HCH3CH20
CH3HONo211 C1(3Qi20CH(CH3)2ii OBr
11CH3C12CH20CH3ha ONo2
HCH3r; H2CH2S(CI42)2CIi3HO
CI IICH, C112CH25C)i3
H', r )i HCH3CH25CH
3HOCH3H CH3CH2CH25CH3HC(X; H3HCH3C
H2QC2H5, HOF HOC1i3C2
H5H 0502C112i:H2OCH31iQC
2H,CH3I Ooso2(Cn2),ocH3H
5CH30H3HO0502C': II2>3C,H,
H6CH3°H3HS Br H5CH3
CH3HOBr8-*1- 5CH3°H35-OCH3 0H 8CH3cH3HOH6-Br 5CH3CH3CH305o2CH, H8CH3CH3
0M30 5C2C2115HQC2H50H3CH3
0CI HQC2) I5CH3CH3° N
o2. 3 to HkIR2. ^ R14”15m,
Giant) 5°2H> CH3II OF
HCH3CH2CH3HHH SC-H3°H3]II J C1, HQC2H5
CH3Ht,,, 6S02aH2clHOc2H5
CH3lI OS(N2CH3HQC,,H2C
H2S O button 2 (CH2) 2C the 3HO°2H5°H
3HO5CH2°H3HOc2H5CH3HOoS02
CF3HoC2H5CH3HO502N(CH3) [(
CH2)2CH3]HQC2H5CH3HQ CH3
H oCH30H3HO0CH3H OC2H5CH3HOFH OC2H, CH3I OC1'
HQC2H5C13HONo2H Oc2H5CH3HO802N(C)+3)2HQC2
H5CH3HO502N(C2H,)2HQC2H,C
H3I 'O502N (OCIi3) CH3HOc2
H5°H3HO0s02CH3HQC2H50H311
0oso2(CH2)3an3HOC2H5CH3HO
8O2CH2CH″c1 (2HQ02H5CH3HO5
o2CF3H "l R2"3 11+ "14 built
0c2H5°H3H0S'-2°F2°F3
HO°H3CH3HOH)1 0CH3CH3HOCH3H oCH30H3HO0CH3H ″H3CH3, HOF HOCH3CH3
HOC1)1 0CH3°H3HOBr HO°H3CH3
HONo2. HOCR3cH3HO502N(
CH3) 2HOCH3CH3HC802N (C only H5)
2HOCR30H3HO502N(C+3)C2H5H
OCR3CH3HO502N (O gate) CH3HoCH3
0H3H,I O09O2CH3HOCR3CI(3
no oso2°2H5HOCH3CH3HO0
802CF31+0CH3°H3HO・5CH311 0CII3CH3HO5OCH3H OCR3°H3HO502°H311 0CH3°H3HC,5O2H, @ OCH3°H3HO802C2H5H OCH3°H3HOS02°H2CH2cH3HFl l
R2R3711414 hair) OCH3C1 (3It
O-''('2CH2CH''CH21(', CH3C
H3HQ 502CF3HOCH3'J (3I C
'5o2CH2CF3HOCR3CI3II 5
O2CH2CHCICF3HOCH3CH2CF3HO
CH3H O°H3°H2°F3HOOCR3H OCR3°H2°F3HOCL HoCH3
0H2CF3Hc, No2HOCH3CH2CF3
Hos02N(CH3)2H○town CH2C'! '3H
cm 5o2N(acIr3)aH3HOCR3°H2
CF3H'-OE'C'2CH3HoCH3°82CF
3HOQS02CF3HoCH3CI2CF3HOso
2c) I3HOCH3CH2CF3HO802CH2C
H2CH3HOCR30M2(:F'3HO5L2CH
2CH=CH2HCI CH3I 0CH3H CI C) f3HOCI , , HCI
CH3I vNo2K CI CH3I c 5o2N(CH3)2H
CI CH3I OQS02°H3HC:L
CH3I O5o2CH3HR1'2 ”3 &
R14"15 NllCH3CH3+1 C"
0CH31+NIICH3CH, HOB! ”
HNHCH3cH5HQ 502N(OCH3)C
H3IINHCH3CH3H00S02CF3HNHC
H3CH3HO5 (2CH2°H3HNHCH3CH3
'H03020M2CH=CH2HC1! (CCH3
)2CH3HOCR3HCHCOCH3)2CH3HO
F HCH(oCH3>2CH3HONo2
'HCH(oCH3)2CM3H0802N(
C2H5)2HCH(OCH3)2CM3HO502C
H3H9) °"5""1" O cH'J CH,HoCH,H -〇O CH) CH3H OCH3
Hl( 0 CH) CH3H'OF, H%0°6°]. H, HC6, □ ゝ0 town)'2 R3, 工"14 ≦, MU'
°〕CHCH31(OBr H−〇′°〕OHCH3)i Q I 02H 0 CHI 'CM, HO502N(CH3)2H0 4°"I] CI, Ho 5o2N(ocH,)a
H,Hl0 6'JCH3Ha aso2aH3H \O cs ]OH,'HO0502CF3H-〇CH,l CH3I OSCH,H /Q ゝ0 0 0H) CH,HO5o2(2H,H-〇CH] cH3HO5o2cH2ca=ci t2H
\0 Q(0,7CH,HO502CH20H20H,H0 CHI CH3I OSO,CH3H 翫O Cloth 11 RIR2R3X,, 1i19
Kumazore 0CH3C113) i 0 (:10CH
,CH3I ONo2 0CH3CH3HOCF3 0CH3CM3HOC02CM3164-166GC0
2C>, HOC02C2H. 0CH3CH3HOC02(CHI2)2CH3QCH
3CH3HOC02(CH,,)3CH30CH3CH
3HOcO2(CH2)4CH3CCH3CH3)lo
cO2(CH2)5cH3OCR3CH3HOCo2C
H(CH3)20CH3CH3HOCO2C112CH
2oC)+30CH3CH3I OC02C1i2C
H2QC2)+50CH3CH3HOCo2(C1(2
)30C2H. 0CH3CH3HOGo2CH2CH=CH20cH3
CH3HOC02CH2CH<HCl(50CH30H
3HOCo2(C12), CH=CH2--Sa! 5
Tsujishoku) OCH3CH3HG Co2CH2°! ICHOCH
3CH3HOca2cH2c=ccH3QCH3CH3
)1 0 Co2(OH4)2CICHOCH3CH
3II OCC2CH(CF3)C; 2H500H3
CH3HOC02CH2CH(CH3)2(5)F3
°H3HOCO2CF3QC)+3CH3HOCo
2CH2°H2C1OCH3cH3HOCc2CH2C
F30CH3CI3HOC02CH2CCI30CH3
0H3HOC02CH2CH,, CF30CH3CB3
HOCo2CII2CH2CH2CIOCH, CF3H
'OCo2CClF20';H3CH3HOC02
CF2H OCH3CH3HOCo2CHFCF2HOCH30H
3HOCo2CHCICF2HCCH3CH3HOCo
2CH2CHF'CF2HOCR30H3HO502N
(0(:F3)CH30CH3(:H3HO,5o2N
(CH3)20cH3CH3HO502N(C2H5)
20CH3CH3H'O' 5o2N(CH3)C
21(.0CH3CH3HO5OICCH3”)C02CH2C
H3hx R2F3 ^ R19 average) QCH3C
I+31i v QSC2CH3C'Cba3CH3
140us02C2H50Ch3CH3rXo os
c+2(Co2)2an. 0CH3CH3If O0SCJ2(CH2)3CI
30CH3CH3I O0S02CH(CH3)2o
cn3CH3HOoso2jn(aH3)c,H. 0CII3CH3HQ 0002C1+2°H2OC
H3CCH3CB511 0 0SO2(CH2)30
CH30CH3CH3HO(,5o2CF3 Qcl(3CH3H・,,0S02C112CF3
QC)? 3. CF3H' O0SO2CIIFC
F,,HOCII3CH3HG cso2cr2ca
2cH2an30CH3CH31i 0 0S02C
GIF20CH3°H3H'O0SO2°Br2CH3
QC)+3CF3HON(CH3)5o20H30CH
3,0M3H,ON(OH3)So2C2H50CH3
0H3110N(Gl,)So2C3H50CH3CH
3HON(CH3)3.02CH(CH3)C,a50
CH3CH3HO, NCCH3) SU2CH2Ck12
0CkL. 0CR30H3HC) N(OH3)So2CF30
CH3CH3HOSCH3 ”1 2 ”3 V, R19d)○CH3
CH3H0SCCH. Q": F3 °H3d OJO2 °H30'koH
3CH3Hc s・2C2H5tX;83CH3i(
Q S(,2CH2°H2□3C・CH3CH3HO
Sr〕2CH(CH3)2QCH30H3Ii OS
o,,CH2CH<H2OCR3el13HQ 50
20H(CH3)C2H. H3°H3HO5CH2°H2°F3 0CH3CM3HOS(:F3 0CH3°H3HO5OCF3 0CI(3C113HO502CF3 0CII3CH3Hc, , O':CI. 00H3°H3Ho o°F3 CCH, CH3HO0CF2CF3 0CH 3'CB3HOOCF'2CF2CH30CH3
CH3HO°CClF2 0°H3CH31100CG12CF3QC2H,CH
31i 0 C0 2CH2CH3HONo2 QC2H5(m3'H・0F 0c2H5CH, HO(:AJ2CH. )'x R2F3 ^, I"119
肚”2) 0ヲ5 °13) i0S″2c2H5
0°2H5CH3HOCo2Cl12CH2CH30C
2H5CH3HOl;O,, CI(6H3)2LC2H
,CF3HOC02el12C)l″C112Q,C2
H3CH3HOcc2CH2CEIiOC2H50H3
H, () CC, 2C1120H20CH Niji 0C
2H5CH3110CO2CI (2CH20C2H5Q
C2H5CH3) i 0 . 0C20F. QC2H5CH3HO502N(OCH3)CH2CH
F, CF3H(J SC2SC2N(CH3)2
0C2)15CO502N(CH3)C2H5QC2H
5CH3Hc sc, 2i(c2u5)2QC2H,
CF3HO', :502CH3oc2n5CH3Ha
os02c2H. aC2H,CH,HQ rj(aH3)sa2aH3
0°2'5 °H3HQ Su2°H30°2H,
CF3HO button 2C2H5 0C2H5ji HO502CH2CH20H30"]2
H5'CF3HO5o2CHCH"CH. 0C2H5CH3HO802CF3 0°2H5cH3H00CF3 "l "2 "3! ”19
Tailoring) QC2H5' CH2OO0CF2CF
3QC2H, 2H, HOCI QC2H5C2H, HONo2 002H562H5HOCF3 0CH3 3N C2H, C2H, HOCo2C2H5'''02H5
C2H5HGC02CH2CH2CH30C2H5C2
H5HOC02CH(CH3)2QC2H5C2H5k
5 0 C02CHCH=CH20C2H5C
2H5)! 0C(2CH2C'''cHOC2H,C,,
115HG CH2CH2CM20CH3QC2H,
'C2H3HO502N(OCH3)CH30
C2H〉C2H3HO502N(CH3)2QC2H,
C2H,HOt+502CH3ce2n5C2H5HO
n(CH3)sO2cH3QC2H, C2H3HO50
2cH3 QC2H5C2H5H (i 5o2CH2CH3QC
2H5￥, li O5u2CH2CH2CH3Q
C2H5°21(, HOO°F3 0CH2C12CH30H3Ho, 'C1oC11
2C1′12°H3CH311CNo2plR2R3;
l R195 ward) 2°H2°H3°H3) i 0 C
F3jiH2CH2CH3CH3++ C, co2c
H OCH2C12CM3CH3)i PaC'2C
H2C1l″CH2C/32CH2CH3CH3110
So, N(OCH,)CH. 0CH2CH2CH3CH3+1, ON(CH3
)&72CI30CH2CH2CH3C13HOS(・
2CH30CH2CH2CB3CH3-HO5o2C1
:2CH2CH3OCR2CH2°H3CH3HOQC
F3C(CH2)3CH3, CH2OOCl0(CH2
)3°H3chi H' ONo2C(CH2)30H3
CH3HOCF. 0(CH2)3waH3CH3HOC02CH3cccI
I2>3CH3CH3HOCo2C2H. o(ca2)3an3CH3HO(X)2CH(CH,
)20(CI+2)3cH30!311O502N(C
H3) 2(, (CH2)3CH3CH3 Summer IO8O2C
H30(CH2)3CM3CM3Hc 5o2CH2
CH2CH3o(C1(2)3aH3CH3HOocv
30CH3'C2H5"IIOC1"l
'2''3 W R197)0C)1
3c2H511ON02 (X; H3C2H, I OCF3 0CH3°2H,, II 0CC2CH30CH3C
2H5II°'-'C02C2H5cc, 3C2H51
f, O, C02CH(CH3)2QC)i,
C,,H,HOCO2CH2Cl(:H2OCH
3C2H51i 0 C02CH2C'H2OCH
30013C2■(51(OCO2CH2CH2C1o
cH,,C2H3HO5o2N(oCn3)an30c
H3C2H5HO802N(a(3)20CH3CiH
5HOO3○2CH3 0CH3C2H5HON(CH3)5C,2CH30C
H3C2H5HO5('20I3 0CH3c2a, HO5c2cn2°1(2C
H30°H3c2H,n OOCF 0CH3' CH2CH=CH2HOClOCH3
'CH=CH''cH2,11' ONo20CH3
CH2CH=CH2,Ll' OCF30CH3CH
2CH″CH2HOCo2CH30cH3CH2°H″
cH2IIOc02C2H5CCII3C112CH=
CI(2HOC?2CH(CH3)2RI R2
”3 Vr R19-return) H3 to U, C112C
1i=cH2i; CG020H2CH=CH2
0CH30H2CH=CH2ii CCo2CH2C
H20CH30CH3C12CH=Town HQ S02N
(Me)2OCR3CH2CH=CH21i t;
oso2cH30CH, CH2CH=CH2HG
502CH3ocH3CH2CH″CH2HO502C
fi2CH2CH30CH3CH2°H=CH2HOo
CF300H30H20CR3' HOCl0CI(
3CH,,0CH3HONo20CH3CH20CH3
HOC02CH30CH3CH20C+(3HOC02
CH2CH2CH30CH3'; H20CH3HOCO
2CH2Cl-CB,. 0CH3CH20CR311O502N04e)20C
H3CH20CH3II OS02°H3OCH3C
H20CH3HO8o2C1 (2CH2CH30C,H
3CH20CH3HOC502CH3CCH3CH20
CH3HO°CF3 0CH3CH2SCH3HOCl 0CH3CH2SCH3HONo2 ocn3r:,)! 28cm3H0C02CH. 1″ to OCH3CH2sCH3HOC02CH2CH3
``2it, ,, R19b'')()GIr3
CH2SCH3CCo2”(CH3)2・-C1(3°
)l,,5C1(3-HCω2(:)12CH heart 2s'
Jiri)! 2SCH3HO5o2r1(Co3)
20CH3cH2SCH3HG ClSO2:H30
CH3C+! 2SCH3i(O502CH30C; H3
0H2SCH3Ht) S':2CH20H2C1i
. (,1CH3CH2SCH3HQ 0CF30CH3
CH2CF3HOCl 0CH3CH2CF3HO'No2 0CH3°H; CF3HCCF3 0CH3CH2CF3HOC02CH300H3C11
2CF3)! OCo2°b2CH″CH2OCR3
CM2CF31+ 0 0S02°H3OCH3CH
2CF3HO5o2CH30CH3CH2CF3HO,
So2°H2CH2C)I3oqn3CH2CF, HO
S02N(0M3)2OCR3r:H2c”cHHOC
020H30CH3Ch2°H20CH3HOCO2c
H30CH3CH2°H2SC:H3J(Oc02CH
300H3 (IH2CH2CH5I OC02CH3
cH3CH3HOC1 "ENG" 2 R3W "19 m...
1. V'::)CH3CH3:: ONo2 0H vH31+
0 CF3CH3cH3I OCo2°)
(〉CH3CB51i 0 Co2C120H''
'CH2CH3°H3HO502N(C113)2CH
30H3HO502C11゜c2n5CH3H(,I C02CH3(CH2)3
0H3CH3If OCCl2Cl. CH2CM″CH2CH3HOCo2CH. CH2G!ICHCH3I OCG2C113E,
CH3CH3I OCo2CH35CH2CH3C
H3HOCo2Cl. 5CH2CH=C112CI(3HOCo2CH35C
H2c02CH3CH3HOCO2°H3CH2°cH
3CI(3HOCo2°H3C1i20C112CH,
, CH3I OCo2CH3CH2°H20CH3
CH3HOCo20H3N(CH3)2cH3H,OC
o,,0M3CF30H3HOC02°H3 238H3H,(” C02°H3 23CF CI CH3I OCo2CH3I11
)'2 to 3+: P! x9.已ゆ)N)[(C1(3
) CH3I OCo2ca3C++(oc
H3)2 CH31+ OCO2CH3jill
3CH3(:B30 gloss 2CH3QC;H3CH3,
+1, 0, C02CH5ocn3CH3H,
s'=o2N(CH3)2och3'OH3,cI
(3O502N(C13)2hekoヱR,R,,R,= paper 祇、ζ″、・USE0C
H3Chi3! I OCl 0(Ji3CH3if G No2(X; H3CH
3HO0F3 0CH3CH3HOCo2CH5 occhi Cf13 11
'-''C○2'ni2H50(:H3CH3H
Q CC2(CH2)2(:I(.OCR3CM3HOCo2(CH2)30H300H3
CH3HC12(CH2)4CH30CH30H3H
Oω2(CH2)5CI! 300H3cn31(a
Co2cn<taH3>20CH3CM5HOCo2C
H2CH20CR30CH3CH3HOCo2CH2C
l2QC2H50CI(3CH3HOCo2(CH2)
3cc2uu0(1m3CH3HOCo,,':H2C
H=CH20CH3CH3HCCO2CI(2CH″C
HCH30CH3CI3HOCo2(0M2)4CH=
CH2QC)! 3CH, ao co2an2c=
cuyu 12 u hel, R19
- and expression rainbow 0CH3C1i3HOCtv2'M2C''cc
H3QCH3>3'HCcc>2 (Ca2) 47 report C
H3C1 Meng3 )1 υ Co2C
:IICCH,>C,,H50CH3e113i(Q
C02CH2CIi(OH3)20CH3C1f3'
6 0 C02CF30(1(3CH3HOC+>
2CH2CH2CIOCR, CH3110c02CH2
0F. 0CH3CH3'HOCo2': H2CCl30°
H3°113 HOC02C82CH2CF30C
H3CH3HQ Cj2CH2CH2CH,, Cl
0CII3CI, )IQ G02CC
IF2OCR3C1(3H(,Co2CF2H″H3C
H311'u C02CHEF2H■H3CH
31'l OCo2CHCICF]CK:R3CH
3) IQ 0020M2CHFC; F211
″H3°H3II, OSo,,N(CXI:R3
)CH30cH3CH311O5O2rJ(CH3)2
0CH3CH3HO502N(C2H,)20CH37
CH3It O502N(CH3)C2H50CH3
0H31+ 0 So, n(CH3)cH20H2
Open 50cH3cH3HCO8O2cH3 3 to RIR2. , R195 area aim OOR3CM3HO+, Q02°2"50CH3'CH
3if v fJs(-2(CH2)
2; 130CH3 town il 0 0502 (CH2
)3,;H3GCH3town H・oso2(:H(Ca
3) 2 sounds 3CH3H○ 08O2Ch(CH3)C2H
50C83G! (3HO0S02':H2°H20CH
30CH3CM3HC0So2 (Z2), OCR. 0CH3CH3HG 0SO2CF30CH3°H3
It D':5O2f:H2CF30CH3
CB3M O0S02CHFCF2HOCR30H
3H,,,0SO2ri F2C1!2C112CH3C pull
3CH3HOC502'':ClF20C:1i3CH
3HO05023r2CH30(')+3':'
l(311, J N(CH3)5・tsu2I; H3O0
H3CO3+! This N(CH3) milk, C-50>3
CH3H'ON(CH3)302C3H5OCR3CH
31i 0 N(0M3)SO2Cl(CH3)C
2H. OCH30H3HON (CM,) So2C112012
0CR. OCH3C113HU N((m3)S02
F300H3CH3Ht,) SCHSCH30
CR3C, O5 (XI: H3 hIR2 to 3 ^ R19 di-type ○CH3CH3HOS・2C,!) I50CH3CH3
HQ 5 (2CH2CH2CH30CH3o+3H
C5c2CH('H3)20CH3CH3HO5o2C
H2CH″CH20CH3CH3HOSo, CH(CH
3) C2H50CH3CH3HO5CH2CH20H3
0CH3CH31105CF3 0CH3°H3II O5OCF3 0CH3'CH3' II O5O2CF30C
H3CH3)1 0 0CCI30CH3C)+3.
, +1 C) 0CF30CH3CH3H'
OOCF, CF30CH3CH3HO0CF2CF20
H50CH3CH3HO0CCIF2 0CH3CH3HO0CCI2CF3 QC2H5' CH3,HOC1 ″2H5°H3HON02 0c2H5CH3HOCF3 0C2H5C)+3HOC02CH3 0C2H5cH3+10CO2C2H50C2H5C H
3HOC02CH2CH2 Town 5 82 Rshi R19
oc2H5CH3HOCo2CH(CH3)2QC2H
5CH3H, CCo2CH2CH=CH2QC2H5C
H3HOC02CI42C*CHQC2H5CH3HO
Cc, 2CH2CH20CH30C2H5CH3HOC
02CH2CH2oc2H50°,,H,CH3I
O°02CF3QC2H,°H3HOS02N (OC
R3) CH3oc2H5CH3HO802N(c)+3
)2QC2H5CM3HOS02N(0M3)C2H. 0C2)I5CH3HO802N(C2H5)2QC2
H5CI3HO°802°H3 0c2+ (5CH3HOO802C2H50C2H5C
H3HON(CH3)S02CH3OCR,CH3I
O802CH3 QC,,H,CH3I O502G,,H. QC2H5CH3HO5o2CH2CH2CH3QC2
H, CH3I O5o2CHCH screw 20C2H5cH
3HO8O2CF3 QC2H5CH3HO0CF3 QC2HQ CH,HOoCF2CF3QC2H,C
$, HOC1 -55 standing, 5th ward QC2H, C2H3HONo2 0c2H5°2H5Hv CF3 QC2H, C2H5110Co2CH30C2H5C2
H51IOC○2C2H50C2H5C2H5,110
C02CH2CH2CH3QC2H5C2H5110c
2Ca(CH3)2QC2H5C,,H5OOCo2C
HCH<H2OC2H3C2H5HOC02CH2Cぢ
BQC2H5(, H5O(Co2CH2Cl20CR. OC2+(5C2H5HO802N(OCH3)cH3
oc2H5C2H5HO802N(CH3)2062M
5 62H5H':' °802°H3■-5C
2H5, n oN (CH3) Shame, Cchi0°2H5°!
5HOS('42°H3QC2H5C2H5HO5o2
CH2CH3QC2H5, C2H3HOStu, CH2
C) i2Cl. 0C21[5°2H5HO0CF3 00112CH2CH3CH3HOCl0CH2CH2
CH3CH3HONo20CH2C)12C)! 3 6
H3HOCF30CH2CH2CH3CH, HOCo2
Cl. --et al. 4+, ``19 m-p-(''')
OC++2G)12CH3CH3Ht″iC・・2;H
2C1(・CH20CH2CH2CH3CH3)1 0
502N(0'l;R3)CH3C・C1i2CHC
112CH2CO502N(CH;)2ocH2Ca2
ch3ca3) 1 0 oso2Cn30CH2CH
2CH3CH3HO, N(CH3)5t-2cH30C
H2CH2CH3 3HO502CH30CH2CH2
CH3cH3HOS02CH2('H2CH3ocH2
cH2cH3CH3H00°F30(CH2)3CH3
CH, HOCl 0(CH2)3CH3CH3HON02o(Cn2)3
aH3CH, HOCF30(Cn2)3CH3CH3H
OCO2CH30(CH2)3(m3CH3HOCo2
C2H50(CH2)3CH3CH3HOcO2CH(
CH3) 20(c)! 2) 3CH3CH3HO802N
(CH3)20(CH2)3CH3CH3HO502C
H30(CH2)3CH3OH3HO502CH,,C
H2CH30(CH2)3CM30H3'HO0CF3
OCR3°2H5HOCl 0cH3°2)I5HON02 00H3¥5HOCF3 0CH3,C211,HO,Co2CH. F″l '2 ”3! R.A.
-Ze! OCH3°21151i 0 C02°
♂50CH3￥5H' Co2CH (CH3>2QC
)13C2H5II l', C02CH2('A
(-CH20CII3C2H, II OCo2CH2
CH20CH30CH3C2H, HOCo2CH2CH
2Cl0cH3,C2H3HO802N(OCH3)C
)! 30CH3C2H5,HG 5o2N(CH,)
. Kui 5C♂, HO0902CK. 0CH3C2H, HON(CH3)5L)2CH30C
H3°2H51i 0 5o2CH30°H3c2H
, HOSo2CH2CM, CH30CH3C2H5)+
0 0CF30CH3CH2CH″CH2HOCl 0CH3CH2CH=CH21i 0 No20C
R3CM2CH=CH2Hc CF30CH3CH2
CH=CH2HOCo, CH30CH36H20H=>
2H, OCo2C,,H. ocH3cH2CH=CH2HOcO2CH(CH3)
2ocH3CH2CH=CH2HOS02N(Me)2
Island, Cl2C11 Tun 21 ((080201'!. RI R2R3W R19 Ji Ni Road 0CR (3C
H2CH=CH2H, OS jin 2CH30CH3CH2C
H<H2O(115o2CH2CH2 gate QC)13C)
12C? CH2HO0CF30CH3CH20CH3I
t OC1O°H3CH20CH3HCNO2 0CH3CH20°H3HOQ; 2°H3OCH3CH
20CH31 (OCH2CH=CH2C1i. OCH3CH2OCH3H') C02CH2CH
``CH20CR3420 town)r O502N (cold
)20CR3CM20Cchi 11'・5o2C
H30CH3(:H20CH3HQ G○2CH2C
I'L2CHsjiR3OH2O 3HOO, 5O2CH
30CH3'CH20CH3HO0CF30CH3CH
7CH3HOCl 0CH3CH2ScH5HONO2 00H3CH2ScH3H0CQ2°! 50CH3CI
2SCH3HOCo,,CH3CN. 0CH3CH2sCH3HOCO2CH(CH3)20
CH3CH2SCH3HOCo2CH2CH=CH20
CH3c112SCH3HO802N (CH3)2 shout■
3CII2SCH3H00S02CH3TLLH21''
5 (+ ”19 concave! fluent; 5 shi
-I2S;H5+i 0 502CH3QCH3CH
2SCH3HO5o2CH2C1i2CH30CH3C
H2SCH3HOOCF 0CH3CH2CF, HU Cl0CR3C
I+,, °F3HONO2 06H3°H2°F3HOCF3 0cH3°H20F3HO°02CH30CH3C11
2CF3HOCo2(J2C1(=CH20CH3CH
2CF3II O0802CH3CK:H3O12C
F3H○ 5C2CH30CH3CH2CF31 (O8
o2CH2CH2CH30CH3CH2CF3HOSo
2? BCH3)2OCR3CM, C=CHHOC02C
M3aCH3CH2CH20C02COCo2CH30
CH3°H2°H2SCH3'HOC02°H3OCH
3C1(2C)i2C)I3)1 0 Co2°H3
CH3CH3HOC1 (J5CM3HONo2 CH36H3h O°F CH3°H3HOC02CchiCM, Cl3HOCo2CH2CH=CH2'l
R2”3... 119 - at
2) Chi Cl3HC5o2N(C143)2CH
3°H3HO5 (2cH3 C,, H5CH3) 1 0 t C2CH5 (CH2
)3CH3ca3HO' Co2°H3CI,,CH=
CH2CH5HOCo2CH3CH2'” cHCH3
110co2CH3SCH3CH3HOCo2°H. 5CH2°H3CH3HQ °02°H3SCH2C
H″CH2CH3HOC02CH3SC)12Co2C
H3CH3)! OCo2°H3CI,,O°H3C
H3HOCo2°H3CJ (20CH2CH3CI3H
OC1)2CH3CH2CH20CB3CH3H('
GO2°H3N(CI+3)2 CH3H
O(con2CH3CF3CH3HOCO2CH3 CF2CF3Cl3HL・C02CH3C1di H
(・ GO2CH3 mon (C113) cH3HQ ■2 town C) i (
OCH3)2CH3H'OG02CH30 CHfu Cl3HOC02C113 -〇hiki "'"3! ”19 Song a (:
H3CH3CH30Co2CH5oCH3,Cl5HS
C02CH30CH3CH,HS so,,N(
Ca3)20Cd3 shiH3CH30SO2IJ(
CH3)2/' Table 13 CH=CH2IIC,, H5Go2C2H5HH0H3
C2H5SO2CH3H CH3CH3C2H, CH3C H2CH, C2H5Br HC) I3CH3
C2H, °1H HCH3C2H5°H3H CH3°h5 °2H5°2H5' HHCH3C
2H, No2H C13CH, C2H55o2(cH2)2an3! IH
CH3C2H55o2N(OH3)2HCH3CH3C
2H5No,, HHCH3C2H50CH3
H di o>3' c2n5Co2ah(qu,)2HH
CH3C75Co2C formula 2CI (Snake H2HCH30CR
, C2H50CF2CF2HHHCH5°2H, Co2
°H3CJ HR1R1' R2° 87
Yu Yomeko CH30CH3C21150S
o2CHCI2HH0H3C2H, CF3H CH3CH3C2H3SC2H5H H0CH3C2H50S02C2H5HHCH3C2H
3Co2CH2CH2CL HCH30CH3C
2H5osO2CH2CH20CH3HHOC2H5c
)I3S02N(oCH3)cH3HH92H5cH3
CO2°H3I ( HC2H5°H3Br HHC2H,C
H3NO2" H HC2H, CH3C□, °) I3H Hoc2a, CH3oso2an2(an2)2o
ca3HHC2H,,CH3CH2' HH,C
2H5C113CL HHC, H5Ca
13CH3H H, c2H, an3□ i, an(at,)2HHC
2H5°H3CI HHC2H, C11
3Co2CH2C)]<H2HHOC2H5' CH3
0SO2CH2CF2HH and R1'R2'
17 size Lm) H0c2H, CH30S
02ec13H110C2H5CH3O802CHCI
2HHC,,I5(1(30S02C13)iHC2H
,CH3CH2°02H5H )I C2)15CH3'S02°2H5TIuO
c2H5CH30SC2CF3H II C2H5CH30CF3. HH002115
0M30CI3H HC2H5013NO25-CF3 H, C, H5C113No23-CI H, C2H5CH3Cl 6-No2HC
,,HCH3C23t-No2 HCH3,C2H,C15-CI H0CH3C2H5NO2'5-CI CH3CH3C2H,5o2N(Q[3)23-CIC
H30C2H5cH3cc'2cH35-C2H5CH
3￥5C1(, C13-Br CB30C2H5013C15-Br CH3,C2H,CH,No26-F CH3QC2H5CH3C1, 5-F CH3QC2H5CH3Br 3-F
R11421R7~, Bao C113C2H5CH3No25-NC20H3°2H
5°l13Co2CH33-CF3C1130°2H5
C113°H3,2CH3°2H5°2H5°02°H
3HCI(3C2H>CH3C02C2H5HGHb
C♂, 2H5'CI HCH3C
2H3tS15, NO2HCH3°2H5C2H
5°H3H CH3C2H, C2H3GO2CTI2CH″CH2H
CH3-C2H5C2115de02C1((CH3)2
HCH3C2H5C2H5S02cH3HaH3c2)
I5C2H5502 (CH2) 2 gates HCH3QC2
H5C2H5'5O2CCH3 on H3C2H, C2H,
5o2N(CH3)2HCH3C2H5, C2H55o
2N(ocH3)aH3HCH30C2H5°2H5°
S02°H3HC113C2H,C,,H5i (Ca
2) 2cH,, HCH3C2H3C2J (5°C2H,
HCH3C2H5°2H5s0H3H H5CH3CH3-Co2CH3H H5CH3CH3So2G13H and R1'R2° 17 Sa -〆Aim
H5CH3C113N02H H5(J13CH3so2N(/J3)2HH5ob3
CH3sc2NtC+3)c2h, HHS(:I
3 °H3C:H3'HH5CH5'CH
3No2H H5CH3CH3C1, Hj,. HSCH3' CI+3O802CH3H, H3CB
3C83Go2CH(::I3)2HH5CH3CH3
Co2CB2CH=CH2'HHSCH3'C
M3C0, cl(2an2cIHH' 5CH3C1
13C02C) I20H2°cH3HH5CH3CH3
,Co2CM(CH3)C2H5HH5CH3CH3C
o2(CH2)3CH3,HH5CH3CH30S02
(CH2)3CH3HH5CH3C1130802(C
H,,)3(JCH3HH5CH3CH3CH20CH
3H H5CH3CH30S02Cl, CF2HHH5CH3
CI3F HH5CH3CI3oso2
co2cC13, HHficH3(T(305020H
2CHCI2HCH3SCH3CH30sO2CF'3
To, ° λ2° ”? R1
Lrz! OH3, SCH3, CH30SO2CHC1
2, HCl3SCH3Q(3,5o2(CH2)2CH
3! (CH3SCH3°H3sC2s(o+3)2HC
H3SCH,CH,5a2N(c2H,)2HCH3S
CH,' , CH3,5o2N(CH3)(cH(c
a3) 2 units CH38CH3CI3C120CH (CH3
)2HCH3SCH3CH3' CH20(CH2)
30H3HCH3S (113CH3so2ca (cp3
)2HCH3SCH,°(3°H2QC2H,H-CH
3SCH3CH3°2H5H OH3SCH5CH3CF3H CH38CI3CH3C15-Br CH5SCH3CH3C16-CI CH5SCH36-ClCH35CH 3CH3No25-C1 (1(3SCH3CH3Co2
CH33-BrC5-No2 cCH3SC) I3CH3NO25-02H5CH3SC
H3, CH3No25-CF3cn3SCH3°H3N
○23-CF3 and “l” “2°”7
"8 ('ri) mm and m- CH3SCH3°H3°CF3H Cl35CH3CH30CF'3H CH38CH3CI (3N026-F CH38CH3CM3C1; 5-QC2H
5CH35CH3CM3Br5-No2 0H38CH3°H3no2. ．． 3-FCH
3SCH3CH5C15-F CH3SCH3CH3NC26-F HSCH3' CH30StL2 (Niji 2HHSCH
3CH30m2(CH2)3Br HH5CH3C
2H5Cb2°H3H H5CH3C,H5CL HHSCH,C2
H5No2H H5CH3C2H5Br HH5CH3C2
H5CH3H H5CH3C2H5CF3H H5CH3C2H50CH3H H5cI (3C2H5CO2(i2) 2 gates HH5CH3
C2) I50S02(CH2)2CH3HHSCH3'
C2H5602N(CH3)02H5,HH8C
II3C2H5S02N(OCH3)CH3HR1kl
l K2° → Engineering 5ze 匝 1 bias■■
-Akebono Ikko■-Ki--1-■Picture-■Shizu■■■■-HSCH
3, (:2115bO2(CH2)2CH3”H5CH
3C2H, °C)ff2HI H5ea3C2H5CF, (CH3)2HIGH3SC
H3C2H,5CF3. l(lCH35CI
I3C2H50S02(CH2)20C)I3HICH
3SCH3C2H5SC2H, HICM, OCR
3CM3C1, HkCH3輿H, C, H, No2H) H0CH3C2H5CH3Hk HOCI! 3. 0H3°F3 H)H
OCH3di Br HkH0CH3CH
3CO2CH,H) HOC143CH3So2CM3H) kl 0CH3CH3SCH3H) HOCH3'
0H30502(CH2)30CR3H)H0CH
3C2H50802CH2CHCI2HtH0CH3G
,,H,0S02CH2CF2HH)H001302M
, 0CF3Hk H0CH3C:2H5SCHF2H( HOCH3C2H5OCH3C2H50SQ2C(HO
C2H5CH3FH( ill R1! lq2° Fi?
"8 bzeyo (QC,, H5CHI3CO2CH33
-Br(”QC2H,CH3SCHCH3H (QC2If, 0M3S(CH2)3CI,
H1oC2H5CI(30S02(CH2)3CH3
HI 0C2115C, H30CF3Ml 21
! 5 °1138CF3HI 0C2H5C1
30CHF2HI 0C2H5CH3SCHF2H
IOC2H5CH30CF2CF21(H[QC,H,
,Cl5SCF2CF,HHI 0C2H,CH3
CH20CH2CH(OH3)2HI QC2H5
CH3cH20(CH2)3CH3HI 0C2H
5CH3CH2QC2H, III OC-, CH,
SCH, H l 2H5CH32°H2°H2°1HIOC2H
5CH3CO2CH2CH″CI(2B

0c2H5c
H3CO2CH(CH3)2HI 0C2H,CH
30502CHFCF2HH: H30°2H5°H3O
S02CHFCMCI3H Lagoon 30CI5CH30 Engineering Department 2
■2FH ;H3QC2H5(m30s02C112CH2CI
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)2CH,) HCH3'”2u5.CB3 s・
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CH3, Su-2C1■2CH(CH3)2HCH3o
c2H5'Cl5oI; u2+x(CH3)2HCH3
0C2H5CH3S 2°I (3' HCl3
C1':,, H5C1l, Co2CH, HCl3C
1', C1130S02CH (shi'3)2HCH3
QC2H, CH3CF3) 1 cH3QC2H, Town 0CF2°F211
HCH3CK;2II5 °2H5CI
HCH3QC2II5C2H5i:, IF2HC
H3'oc2H5G215 502(CB2)2>3
HCH30C2H5C,! 1'l5C02°♂5
H:H3oc2H5C:H3O502(CH2)3CI
HHCH3CH3Cc2CIi2CH2CH2
C112CH3H)I CH3Cl3Go2CH2
CH2CI20H2C82CH3H11CH3C:kI
3 Ct・2CB2C1120CI2CM3HH0H
3CH3C(i2CH2CH2C120CH2'TH3
HHC1(3'113'Co2°H2C1''C1N
2BHCH3Cl3G! , 2°H2C1i=CH″″C
H,FHCH3""li3 C02LIi2C1l
=CH-CI・2CH, HHCH3:H3Co2CH,
, :H″CH-f tll2CH2C13HHCH3CH
3(:02el12C TownHHHC113CH3::o2
°H2°“C-CH3HHCH3CH3CC2CH2C
``IC-CH2CH3'' HH H3nH3C02C
H2C'! llm-Cl12CH2CH3HII
C1(3CH3C!・,C112CF3+1H,'
CH3'CH3'X,'2°;・2°013HHC1
3CH3C (42C, ll2CH2C1HH, CH3C
H3C○2Cn12CH2F HH(,m,
CH3Cl2CL2CH3HHCH3CM3C
12Co2CH2CH2Ci12CH3HHCH3CH
3CH2Co2CII2CH20CH3HHCH,CI
(3 Pilgrimage 2GO2CI2CH2(:l HHCH
3CH3CB2502CH2CH=CH3HHC13C
H3CH(CH3)Co2CH3HHCH3CH3CH
(CH3)Co2CH2CH2CH2CH3HHCH3
CH3”0H (C13)Co2CH2CH20CH3H
HCH30M3 CH(CH3)LO2CH2C1
2CI HHCH3CH30H(CH3)Go2C
H2Cl to H2HHCH3CH35CB2cH=C) f
2HHCH30H3SOC112CH″CH2HHCH
3CH35o20H2CH″CH2HHCH3CH35
CH2cH"0H-Cki3HH' 0M3CH3S
OCB2CH-CII-CH,HHC)13
C13Sb2CHSb2CH2C1 (=-CHHC
H3CH3Cl2SCH2CH″CH2HHCH30M
3CB2sOCH2CH=CH2HH' CH3CH3
CH2502CH2CH=CH2HH'CH3CB5C
H25CH2CH<H<H3HHCH3CCH3CH3
CH25OCH2CHCH-CCH3CH3CH250
2CH2CH=CH-CH3HHCH30H3an(C
H3) scu2cn=ca2HH' CH30H3a
H(CH3)sccn2an-CH2HHCH3CH3
-CH(CH3)5L'! 2CH2CH<H3'H
HCH3CH30M(CH3)SCH2CH=CH-C
H3HHC13CH3CH(C13)S(nCH2CH
-CH-CH3HHC13CH3an(CH3-)s(
・2CH2CH=CH-CI, HH0H3CH3N(
CB3)s<)2cH3HHC13CH3N (to H3)
S(,2CH2CH2CH2CH3H)I CH
30M3N(CH3)802CH2CH2UCH3HH
CH3(m, N(CH3)5L'2CH2CH2C
To H20CR31 Rlo R2° R7yu -♂zuH0M3OH3N((':H3)So2CH2C12C
IHHCH3Cl13N(CH3)so2C)
+2Co2F HHCH3(1(3CH20CH
,H HCH391+3. C12C1C12C120CC13
CH3(',)120C)12CI3. HH
CH3CH30H2C)120CH2C83HH,CM
3CB50CH20H″CH2HHTh 0M3CH
30CH,, CH=CH-Cl5HII Q(3C
H30CH2C'''CI HHCH3c
a3ocH2c=c-cu3HH,,CH3,CH30
CR2CI HHCH3°H3oc1i
2FH Hca3CH3ocu2mu3)L HcH3cH30cH20cH2CH3HHCH30M
30CB2CH2CL HHCH3CH3
0CH2CH2F HHCH3CH30
CR2CM20CH3HHCI'13C1 (3°cH2
°H2″l (2°151HOCH30H3Go2CH2
CH20CH2CH3HHOC113CH3C02C)
12CJ′l2CH2oCH2CH3HHO to H3CH
3CO2CH2CH=CH2HH0C113CH3CL
2CH2':H=CH-CH3HH0CH3CH3Go
2CH2CH<H-C, H2CH3HH0CR3CH3
Ca2CH2CH″CH-C12C)I2CB3HH0
CR3CH3Go2CH2C@CHHH0CH3C:H
3Co2CH2C=C-CH3HH0CR3CH3Co
2CH2C"C-Cl2CH3HH0 (J3CH3Co
2CH2C Now CH2CH2CH3HII 0CH3
CH3CI: 2°H2CF3. HHCXI:H3CH
3Co, CH2CCl5HH (X: H3CH3Co2C
H2CH2C1, HH' 0CR3CH3Co2CH2
CH2F HH0CR3CH3CH2CO
2CH3HH0CR3CH3CI! 2002CH2CH
2CH2C13HH0CR3CH3CH2C (2C12
CH20CH3HH0CH3CH3C)I2Co2CH
2CH2C1, HH0CH3-CH2CH2O(・2C
■2CH=CH2HH0CR3CH3CH(CH3)C
o2CH3HH0CH3CH3CH(CH3)Co2C
H20H2CH2CH3HH' 0CR3CH3CH(
CB ) Ct, 2CH2CH2QCH3H main-1:2
R1'"2"7
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H3CH3'5CH2':, H''CH2)HH0CH3
CH3SQC+42CIl″CH2Hli 0CH
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SO2CH2°H=CH-+SH3HH0CH3CH3
CH2SCH2C11′″CH2HH0CH3C113
CH2SOCH2CH=CH2HHOCR3CM3CH
2f302CH2CH=CJ HH0C83C
B3 °H2SCH2CH"C1i-CH311H
0CH3CH3cH2SOCH2°H-CH-CH,H
It 0CH3CH3°H2sC2°112°H=
CH-CH3HH0CH3CH30H(CH3)SCH
2CH=CH2HH0CH3CH3CB(CH3)Sc
CH2CH;0M2HH0CR30H3CB(CH3)
802CH2CH=CH3HHocH3CH,CH(a
n3) scH2cH-an-cH3HH0CH3CH3
cu(CH3)so2cn2cn=cn-cH3HH0
CH30H3NC; I3) so2aH3HH0CH3C
H3NCCH3)502CH2CH2CH2CH3H and
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H3HH0cH3CH3NCCH3>5o2CH2CH
2CH2C>3HHOCH,cI(3N (cJI,)
sc2CH2CH2CL HH0cH3
CH3N(CH3>5r22CI+2CH21HH0C
H3C13CH20CH3H H0CH3CH30H,, CH20CH3HH0CR3
C1(3CH20CR2CH3'H110CH, C:H
,C112CH20CH,,CH3HH0CR3CH3
0CH2CH″CH2,BH0CH3CH30CH2(
:H″CH″″CH3HH0CH3CB3ocn,,c
=ca, HHOCR3CM30CI(
2C″c-CI3HHoCa3CH3QCH2CL
HHO°H3°H3OCH2F
HHQC)I3CH30CH20CII,
HHOCH, CH30CH20CH2CH3H
H0CR3CH30CH2CH2CI H
H0CH3CH3' 0CH2CH,,F
HH0CR3CH30CH2CH20CH3HHO
CH5CH30CH2°H20CH2CH3HH5CH
3CH3Co,, C112CH2CH2CH2CH3H
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'8 ('C)HSG)+3 CH3C
2 H2G+12': H2C82C112CI13
Hli SC:I3. CH3CO2':H
2C1i2ccIl,,CH31iHSCH3°H3C
I12°+12C:H2t (J12CH3HH
5CH3CH3C(2C1i2CH,CH21(H5C
H3CH3c○2″H2CH″CH-CI(31(HS
Hit3CB3C02C11,,CH″CH-CH2CH3
IIH5CH3C113C: 2°H2°H=CI(-
C) +2°112°H3MH5CH3CH3Co2CH
2C TownHHH5CH3CH3Cc゛2CH2C:c-C
I3I+H5CH3CH3co2cH2c=c-an2
an3HH5CII3Cυ3C02CH2C Tsukasa-CH2
C) I2CH3HHSCH3°H3CO2CH2CF3
° HH5cH3°H3C02CH2CC
13”H5CH3C)13Co2CH20H2CI
HH5CH3CH3Go2CH2CH2F
HHSCH3di CH2Co2CH,H
H5CH30H3C)12Co2(:H2CH2CH2
CH3HH8CH3c)I3CH2CO2CH2CH2
0CH3HHSCH3CH30M2Co2CH2CH2
CL HHSCH3>5. CH2Co2°H
2CH″CH2HH5CH3CH, CM(CH3)Co
20M, 11 and R1” R2° R7
~ A set of 5H5CH3CH3 to CTl(CH3)Co2
CH20i12C12CH3HHS to H3CB3CH (
C1i3)C! J2(li2CH2(, CH3HH5C
H3CH3CH(CH3)Co2CH2CH2CI
HH5CH3CII3CH(CH3)CQ,,CH2
Cl”CH2S)I 5CH3CH3SCH2CH
=CH2HHSCH3CH3SCH3CH380CH2
C5CH3CH3502CI2CH<H2HH5CH3
CH3St;+(2';+l-Cl''''CH3HH5d
3CH3soCa2cH=cH-cn3aH8CH3C
B3' 5O2CII, cH''Cl-CH5HH5C
H3CH3CH2S';H2CH''CH2HHSCH3
,CH3C,ll2SOCII2CH=CH2HHSC
H3, CH2Cl,,5o20H2CH″cH2HH5
CH3CH5CH2SCH2CH=CH-CH3HHS
CH3,OH3°H2S (X:H2CH=CH-CH3
HH,5CH3CH3'C112So2CH2CII=
CH-CH3HH5CII3(:H3CH(CH3)S
CH2CH sum H2HHSCH30H3CH (to H3)S
QCH2CH=CH2HH5C113CH3C)i(C
H3) SO2CH2C+ (=CH3HH5CH3CH3
CI+(an3) sea2an duck H"": H3HH5C
H3CH3CH(CH3)SCCH2CH"CTl-C
H5HR・Plo R2° R7 Asahi,” H5CH
3CH3CH(C113)SC22)12'”H;:H
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3HHBCH3CH3NCCH3”)E, (:2ZH2
'H2' )+2-)t, HH5CH3CH3r;
(CH3) So2′=2゛n2ocu3HH5CH3C
I3t;(chi)S(2CH2CH2CH20CH3HH
5CH3CH3N(CH3)SI21. :H21shiH2
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2Cl2F HH5CH3CI3CH2LCH3
)I H5CH3CH3CH2CH20CH3HII 5
CH3CB3CH2C; CH2CH3HH5CH3CH
3CH2C)i20CH20H3HH5CH3CH30
CH2CH=CI(2HH5CH3CH3(X; H2C
H″CH-CH3, HH5CH3CH30CH2 (jc
HH H5CH3CH3ocH2c'<-cH3aII
5CH3CI30CH2CL HHS
CH3(m30CH2F HH5CH
3CH30CH20CH3H H5CH3CH30CH20CH2CH3HH5CH3
CH30CH2CH2CL HH5CH3
CH3ocn2aH2p Hdan 1・
1° R2° R7 5% type % :3) :2 2° H2'
R7 2nd base, 1yu□, 2shu) CH3Cl3C
H3CH(':n3)Sa2t;I2(:H=cH3H
CH3CH, CH3Cl(C)13)SCH2(JI duck
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) S knee CH2CH=CH・CH, HCH3CH3CH
3CH(CH3)SL2°】l2CH“0H-CH3H
CH3CH3CH3N (C1(3)SL, 2CH3HC
H3Cl3CH3N (C) Engineering 3) S・-・2CH2CH
pc112CH3HCJ(3CH3CH3N(C)13
)s(2CH2c)I20cH3HC)13C1(3C
H,N(CI3)So2aH,aH2ca2oca3]
(di CH; CH3N (CI(3)8020M
2CI2CL HCH30H3C)15NCCH,
>m2Cki2cH2F HCH3Cl3(m3
CH20CR3H. CH, CH3CH3CH2CM2O0H3HCH3C)
13CB3CH2DCH2CH3H':H3CH3CH
3CH2CH20CH2CH3HCI3CH,CH,9
CH2cH=CH;, m0M3CH, CH3
0CH2CH-CH-QH, HCH30H3CM300
H2C"CHH('H3CM3 Town 0CR20t
'C-CH5Hch3CH, CH30CH2CI
HCH3CH3Cl30CH2F'
HCH30″(3CH3CK:I20CI3
H and 11° 12° '7 ~-ro
Yu) OH3CH3Cl30CI! 20C112CH3H
CM3C+(3CH30CH2CH2C1, HCH3C
H3CH30CH2(”, H3P HCH
3' CH3,Cl30CH2C+I20CH,H
CH3Cl3CH30CI2CH2(if しJ(,CH
3HCH3QCH3CH3Go2°::H12ZH2C
H2CH2Cd3HCH30CH3CH3G02C)i
2C;I2CH2:;)i2'J20H3HCH3QC
ii3CH3Co2CH2CH20CII2r;)i3
HCH,'OCH3,CH3GO2CH2CH2
CkL2:CJCH3HCH30C1i3CH3CO2
C112CH咄2HCH30cH3CH3Co2CH2
CH=CH-CH3HCH3CjCH30H3Co2C
H2CH=CH-CC2CH5HC)130cH3(1
13Co2(:H2°H=CH-t', HCH30'',
HCH, 0CH3CH3CO2C Agency 2C Police CHHC
H3' 0CH3(IT(3Go2C12C″C″″
C11311CH3□H3CH3Co2CT! 12CF
, HCH30CI(3CH3Co2CH2
CCI3HCI (30CH, GI, , Go2C
H2CH2C1l(CH30CH3CH3C02CH2
CH2FH522 kl' -) (2°
R72 Yu 5,8 Yu 3 Goshi 2-CH30CH3C
H, CH3CI2CH3HCH, shi (]CH
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('TSH3GH,II':J12C-・2::ll2C
H2CI HCH30″:H3CM3CH2CO
2CII2CH'CH2HCH3(IcH3/;I3:
:II(cli3>CC2CH5H”H,aCH3CH
3CH(CH,>C02cH2cH2CHf,H,H>
, (ノCH, しCH3”, JI(
,",113)C"-2CH2CH,vCH3HOH3
oar3ca, q+r<cH3)co2qu2ah
2cl' HOH30CH30H3za (CI3)
cc, 2”, a2cH=or2HCH, 3,0CR3C
I3S':H2Cl1=CI(2KGH3,0CH3C
H3SOGH2':Ii-+22HCH50CR3LI
4. 'St;,,C112CH=CH2HCH30
CI3 0M3' 5CH2higo-(+H3H
CM, 0CH3C113SOCH2Ckl-4-
CH, I (CH30CH3CH3St 2C82°5I
``CH-CH3HCH3 shout, CH, Cl2S carp 2
CH=CH2klCH30CH3CH3CH2SOCH
2C) i″CH2HCH30CH5CH3CH25v2
CH2CH″C)12HCH30°H3CH3CH2S
CH2CH=C)I-CH3HcH30CH3CI(3
CMIOCII2CI(4-aH, HCl(30CH3
C; 113°H2S02°112°1l=c:H-
OH, H゛yu H30CH, Ji C1・(CH3)
5aH2zH-CI2HC)13
300 million CH3cH(I3)s(,:H2z*+=cn21
(CB30CR30H3CM(Cii3)S(J2CH
2CH<H3HCH3 times 3CH3o+(CH3)Scn
2cn=cH-cI(3HCH30CH3CI3CH(
CH3)SCCH2C1l=CH-0M3HCI3oc
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, HcH3oCH3CH3N(St3)Sc2cn3H
Town 0CH3cH5N (OH3) So2OH2CH2CH
2CH, HCl5 0CH3C113NCQH
3) SC,2CH2CH2(,CH,HCl1.0
CH30113N(CH3)So2CH20H2C12
0CH,HCH,0CR3CH3N(aH3)sc2c
H2an2cIHsu, OCH,0M3Nccu
3) so2r, u2an2r HCll30cH
3C) I3CH20CH3HCH30cH3CH3CH
2°H2OCH3HCH30CH, CH3CH20CH
2CH3HCH30CH3CI3CH2CH20CH2
CH3, 11 Town 0CR3CH30CH2C1i″C
H2HCH3QCH3CH30CH2CH=CH-CH
3HCH30C'H3CH,0CR2(:EHHCH3
0cH3('H30cM,,cL-aH3H'-R1'
R2R7”8 J) CIl3 °di CH
30CH2CI HOH3r-tcH3C
H, °cH2F Hgg t・2
H32; +3 °CH2OCH31HCl30',
:+3CH,0CH20CH2C1i. 30CH in C1, CI(30CH20H2C1)Ic+
3 ta:+3 CH3CCH2CH2
F HCH3octt3
CH3■H2CH2OCH3HCH3' OCH3CH
3ocH2(J12QcH2CM3HCH3SCH3C
H3C:02C12CH2CH2CH2CH3HCH3
8CH3CH3GO2CH2CH2°H2CH2CH2
CH3HCH3SCH3CH3CO2CH2CH2GC
112CH3HCH,5C113CH3Go,,CM2
C) 12CH,,0CR20H31+CH35C)+3
°H3GO2CH2CH=CH2HCH3SCH
3CH3CO2CH2CH<H-CH3,' HCH3
9CH3co3Co2C+2Cl''CM-C12CH3
HC13SCH3CH3CO2CH2CH″CH-C+
2Cl2°+3 HCH35CH3CH3Co211
12C phrase HHCH3SCH3, CH3C02CH2CI
C-CIl, HCH35C+13C13C0
2C) i2eIC-CH2C13HCI3 5
CH3C1 (3C02C1+24jC-C12CH2C
13HCH3SCH3CH3°゛2C) 12°F3
H” “L” “2” “v-Satsuji
Mu CH35CH3CH3'X2 Pa・+2(:CC13H
C, SC) +3 Chi C゛22 pieces H2C2CI
HCH3SCH3°H3, C't2°1127+H
2F HCH38CH3' C+3C+2G
o20H3HCH35CN, CH3Cl2Co2C
H2C12CH2CH3)(CH3SCH3C13,,
CH2 02CH2CH2L)C143)! Town 5C
H3CH,C+2rho20H2C1(2C11(CH
3SCH3CH3C+2Go2Ck12CH-OH21
1CH3SCH3CH3CH(CH3)Co2C1(3
HCH3SCH3 Town CI (CI10., CH20H2
C1 Supervisor 2CH3HCH35CH3CH3Ca (CH3)
co2Cn2Ch2(・CC13HCH3SCH3 gate
CH(C115)Co2CH2CB2C1, HCH35
CH3CH3CH(CH3)Co2CH2CH=(:+
211C+3SCH3CH3SSH2C1 (=cH2H
CH33C)I, CH3socu2CH=cH2H
CM3sou3C1 (3so2cH2cn=cH2H. CH3SCCH3SCH3CH3S0H2CH=CH-
CC13HC,,CH35Oc112CI''CH-C1
3HCH38CH3CH3So20H2CH=CH-C
H3HCM3SCH3CH3an2sCH2cH=cn
2+; CH38CH, CH3CH25OCH2CH=C
H2H and kll h2 scream 7 15
Ward 5CH3SCH3CH3CI (2SC, 2CH2CH
″CH2HCH35CH3OH3CH2SLCH20H
Hat 1-CC13HC) 133C113CB3Q12s<
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;+2St,,2CI,,OH fence! -C+3HCH33
CH3CH3CIl(CH3)SCH2CH=CH2H
CH3SCH3C113C11(C+3)+3(XJ2
CH=:182HCH3SCH3CH3CH(CH3)
SC2C12CH=C;+3HCH33CH30H3C
Il(OH3)'; CH2CH=CH-0H3HCH,
SCH,CH,CHCCH,')E,CJCH2CII
? CH-CH, HCH35CH3CH30H (CI(3
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3CB3N(C+3)SO2C+3HC)138CI(
3CH3N(C)+3)St-2CH2CH2CI2C
H3HCH,5CH3CH3N(CH3)So2cH2
cH20CB3HCH38C113CH3N(CH,)
SO2CH2C, H2CH2OCl5IICH3SCH
3CB3N(CH3)902CH2CH2CI H
CH3SCH3CM3N(CH3)SC2C12CH=
CHCH35CH3CH3CH20CH, HCH38C
H3(1:H3CH2CH20CH3HCB31fiC
H3CH3C1120CH2CH3HOH38CH3C
I3cH20H20CM2CH, HCH35CH3CH
30CH2CH＜+2I (and engineering temporary
5-Sada) CH3SCH30H30GH2 (,k・=Cl1-CH
,HCH35CH3C113JC)+2C"";HHC
H3SCH3°H3OCH2,:=rnee CH3HQH
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H3CH30C112F)lC)138C
H30H30cl (20CH3HCH3SCH3°H3
0”ll2(:CH20H3HCH38CH3CI30
CH2CH2CI HCH38CH3CM3.
0';+2°82F "0H3S("1(3C
H3L, :+2:+2°C3HC+3SCH3CH30
CH2CH,,OCH2CH3H(・ 1;
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2H5di cl CH3°2H5°H3ril CH3°2H5'''H3'CQ2CH2CH20CH3
CH3-"C2H5C2H5-C(12CH22H
(CH3)2CH3C2H50H3s-2N(t;n3
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H3HCH3°2115S"'H3 HC2)15; H2S(CH2)3CH31'I
C2H> dH)F and RlI +・2°
G16 Eyu, Yu
Roiler λHC2H5°i13 °+13 HC2H, CH3! -:J2CH3 HC,! H5 2I (5 Knee Z4H9 H5CH3r: H3x3 H-) CH3ck13 h HSCH3°It3'I HLC113CH3N ('2 HS' H3cn3., := H5CH3CH3CI H5CH3CH3CI HSCH3'CH3,S~"2°H3H JC1302
H＞S02 Town HS”:H3y;H3502N(′]H3)2HCH3
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SCH3'C2H3Co2C, H2CH2C111SC
H30H3C02CH2SH(CH3)2 and )'l
'5' し 1 set HSCH 3° 2H
5 knee 04H9 H5CH3CH3SCH3 H5CH30H3' 5(CH2)2CH3It
SCH3°n3F 1 (5C2H5°H3, CH3 H5C2H5°H3SO2CH3 II 0CR3C2H, CI H,0CH3C2H5, CI H0CH3C2H5H HO°H3C2H5F HOCH302H5H HOCH3°l5H H0CH3C2H5, CI H0CH3C2H5St'2CH3 fl' 0CR3°2) 15 °F3H0C
Q3C, H5No2 H" QC2H5CH3CH3 HOC2H5CH3oc2H5 HOC2H5cH3CI HQC2H5CH3So2°H3 H0c2H5°H3SO2°H3 and Rlo 12° ) 116 -〆
匝HOC2H5CII3SO2N(CH3) [(CI(
2) 2CH3] HOCH3COCH3C2H55o2N
(COCH3°2H5SC2N(CH3)OCH3HO
CH3c2H5S02°2H5 HOC2H5CH3SO2(CH2)3CH30H3Q
C,,H,cH5CI CH30°H3°2H5E02 CH30CH3C2H5CI CH30°H3C2H5Br CH30CH3C2H5oC)i3 CH30CH3C2H5SO2CH3 CH30CH3C2H5So2CH3 CH30C2H5GN (380 2cH3CH30CH3
C2H5So2cH3 CH30 town C2H5,5CH3 CH3, (]C5-15CH,5(CH2)3 town CH3
0C2H5CH3SO2N(CH3)C2)15CH3
QC2H, CH3CF3 CH3°cH3°21 (,Br CH30°H3°2H5N02 CH30CH3C2H,B-03H7 and R1'82° 116 520)C
H,oc21I5CH30CH2(CH,,)2CH3
CH3QC2H5 town ○CH20H (CH3) 20H
3°C2H5CH30(,H5'Jl, (JC113CH3Co2CH2°n,,
fA) I3CH30CH3C2H, Co2(CH2)3
0CH3CH30CH3C2H5C02(CH2)20
cR3CH30C2H5C2H5CO2CH2CH2C
ICM30CH3C2H, 602°2H5 (J1300
H3, (, It5GO20H3CH30Cfi5C2H
5SG2NCC2H,)2CH3scu3CH3So2
N(chi)2CH35C1i3CI3So2(CH2)3
CH3CH3'5CH3CH,S(';H2)3C
H3CH3SCH3CH3SO2C:H2Cl(CH3
)2cH3,sc1+3CH,5CH(zH3),. C23C2H, CH3No2 CH3SCH3CH3KO2 (m3SCH3CH3Co2CH2°H2OCH3CH
33CH3CB30-CH(CH3)C2H5CH38
CH3CI3so2(cH2)cH3CH3oc2H5
°2H5F CH3SCtt, CH35o2N(OCH3)C
H3-15 z RI R1+ R21R ratio fusion
point) -m-. CH3I C2H,, C02CHC02CH3C
H3CH5C 2H5BrCH3C, Co2C; H(CH3)2CH3
(:R3C2H5No2 CH3CH3C2H5H CH3CH3C2H5CI CH3CH3C2H5' Cl CH3 gate C2R3CO2CH2CH''CH2CH
3CH3C2H5C02C1■2CH2CICH3CM
3G2) 15C02CH3 CH3CH3-(2H5So2CMI CH3CH3C2H5So2NCCH3>2CH3CH
3C2N(5N02 CH3CH3C2H5S02N(CH3)OCH3CH
3C211> CH3SO2CH3CM3C2H5
CH3Br CH2CH2°2H, Br CH3CH3C2H3CI CH3C2H5C2H5Br CI(3C2H5C2H5CO2CH3)I C2
H3C2H,5o2CH3HC2H5°2H5S02°
H3 HC2H5C2H5cO2cH3 HC2H5°2H5H H9H3°2H5H HCH3°2H5H HC2H5CC2H5C2H55o2N (C' C
2H5°2H5Br HCH3°2H5F HC2H5°2H5F 1 (5CH30H3Br “kl” “2” : “18
m, p, (0r,)11 SCH3°H3Br HSCH3,CH3Br HSCH3°H3H H5CH3CH3CI H5CH3CH3No2 H5C)13 °H3So2N(CH3)C2H5
H5CH30H3sc2N(cH,)(an(an3)
,,)CH38CH36H3F CR35CH3CI3H CH39CH3C)13' H CH,SCH3°H3H CH35CH3CH3So2CH3 CH3SCH3CH3C02CH3 CH3SCH3CH3S02N<CM, 5)2CH3S
CH3CH30C2H. CH35CH3CI3H ”R3SCH3CH3C02(CH2)3CH30H3
SC) 13C) i3Co2CH2CH20CH3cH3
ScH3CH3H CH3' 5ea3. an3ocu(an3)c2
n5CM38C) 13 6H3CH3 Hi R1" R2° R18 Uni) CH3SCH
3CH3SC)+3 0H3stshiH3CH3! ”(Cn2)3CH3CH3
SCH3C2H5So,,C2H5GH38CH3CH
3Go2CH(CH3)2CH3SCH3CH3Co2
CM2Cl″CH2CH35CH3C2H,°02°H
3 CH35C)13C2115Br ci et al. 5CH3C2H,5o2CH3C1(3SC
H3C2H, Cl CH35CH3C21 (5NO2 H0CH3CH3Go20H3 H0CH3CH3so2N(CH3) c2a5p
OCH3CH3Br H0CH3CH3CI HO°H3CH3N02 HOCH3CH3SO2CH3 H0CH3CH3SC2CH3 HOCH3°H3802CH3 HOCH3CH3S02 (CH2) 2c) I3H0CH
3CH30CH3 HQC2H, CH30(CH2)3cM3 and %'
R2° R18 complete set aiming HOC2H5CM3C0
2C112CH=CI,. H0CR30H3″:a,,′,H2CH2CIH0C
H3C2H, C'2C1l(C1+3)2■(○CH3
'C,,R5ri02(CII2)2CH31!0C
2H5CH3CO2C2H5 HCCH3C2H5CG2 H3 HOCH, C2H3CI HOC2H5°H3Br H(■3C2H5S○2CH3 HO Town C2H5502(CH2)3CH3CH3・
CH3C2H55O2CH2CH(CH3)2CI3
This CH3C2H, 5o2CH3CH3' 0
CH392R5So2°H3cM30CH3C2H,S
c'2CH3CH30CH3C2H50C2H5 0H30(1(3C2H,F eI2(X:M3C2)15F CH30CH3C2H5SC2H5 CH30C2H5CH3S02N(OCH3)CH3C
H30C2)! 5 °H3SO2N<CH3) [(C
H2)2CH3]CH3oc2H5CH3H '-"l'R2""+18 m
,p,('C)CH30C2H5CH3NO2 CH3OC2H5CH3Co, ,CH(CH3)2CI
13QC2H5CH3Co2cH2CH=CH2CH3
0C2H5CH3CO2°F, 2CH2CICH3CK
:2H5C1i3, cH3CH, 0C2H5CH3
CH(CH3)2CH30C2H, CB3an2an(
CH3),. CH3'Of;2H5,CH3CH3CH3°C,H
, cH3scr2c; CH3oc, H3CI on C5 CH3QC2II, CH2O,, H5CH3QC2
If5'CH3No2 CH3°02H,'CH3Br LH32H,Cl5CI CH3QC2H5C2H5CI OH3QC2H5C,H,, Co2CH3CH3('C
2H5C2H5, 5O2CII3CH3Q"2H5C2
H55O2N (CH3) 2H flash, 11J (5C2H5!
102 )I OC2H5°2H5Br HOc2H5C2H5c02cH(CH3)2ko R
1'R2° R18m, pJ', ;) Hc(CH3
°2H5502C2H5)! 0C83°2H5F HQC2H,CH3c,cp(CH3)2CH3QC2
H50113S○2(CH2)2CH3CH30C2H
5CH3So2CH(CH3)2CH3QC2H5CH
3So,, N(C2)+5)27 /' / R' Dan 1□1° 12° 818
Paper fish υ'H3, HC2H, C(J, CH3 (II3C8, C2H3Br CH3CH3C2■l5cO2cH(CH3)2CH3
°H3C2I (5NO2 CH3°H3°2H, H CB3CH3C2H, Cl CH30H3C2H5CI CB3CH3C2H5Go20H20H"CH2CH3
CH3C2H5■2C)12CH2CICH3CH3C
2H5+2CH> CH3CH3C2H55o2CH3 CH3°,, H50H3So, town CH3C2H5CH30CH3 CH3CH3C2H5So2N (CH,)2cH3'C
H3C2H,,N02 CH3CH3C2H5S02N(CH3)oC)! 38
° P1')'2° 118 □9. (
・ ・) CH3 ° 2H5CH3S02 ：: H3 CH3 ° 2H5LH35L21 ”H3 O113 ° 2H5CH3BR CH, CH3C2H, BR CH3 ° H3 ° 2H5, 81 CH3 ° 2H5 'BR CH3C2H3C2H, CO2'X, H3HC2H3C
2H5So2C)! . HC2H3C2H,5o2N(CH3)02H5H,C
H3, ¥5 5o2(CH2)2:H3HG2H5C
M3SCH. H82H5Cノ45S02CI3 HC21 (5°2H5°02cH3 HC2) B5 °2H5H HCH3C2H3H HCH3C2H3H H'; 2H5C2H, 502N(CH3)2'A
C2H5C2115Br HCH3C2H3F HC2H502H, pH H5CH3CI3Br R"I<yo°l'2 ・
R work 8,, work 1
25. Yu ('C). H5CH3CH3Br HSCI I3 LH3Br H prisoner (3CM3H rI 5Ch3 ”B3 CIH5C
I(3CH3No2 o r, CH3c113So2N(CH3)ca5
ri S to CH3Cl13 5o2N
(CB3n(CH(CH3)2)OH35CH3CI(
3F CH3SCH3°H3H CH38C)13CH3H CH3C23cH3H CH3SCH3CH3So2°B3 CH,SCH3CH30020M3 CH3SCH30H3So2N (CI+3)2GH3S
CH3°H3QC2H5 CI38CH, °H3H CIL3SCH3CH3CO2 (Tsu B2) 3CH3CH
3SCH30H3co2CH2CH20CH3C113
CH3S(w13 CH3oCn (CH3)C
2H5CH3S';l (3°H3°H3 8° )'1° )'2° 1ゞ16
CH3・SC)+3 °l! 3SCH
3CH35cH3CH3S(”B2)3CH3CH35
CH3C2H5S○24':21 (5CH3SCH3v
u3Co2::n(CH,)2CI3SCH3°H3C
O2CH2"H"CB2CH3SCH3°2H,',0
2C1+3C13SCH3°2H5Br CH3SCH3°2H5S('2CH3CH3SCH3
”2H5C:l CH3SCH3wa5N02 HOCH3°H3C:02°H3 H0CH3CH3Go2N(CH3)C2H5HOCH
36H3Br H0CH3CH3CI HOCH3°H3N02 HOCH3α3 5O2CH3 HOCH, CH3S020M3 H0CH3CH3So2CH3 HOCH3CH3So2 (CH2)2CH3Hoca3
CH30CH3 HQC2H5CM30(CH2)3CH3RI R
lo R2° Rla! , J tumor and) H
QC2H5CH3Co2C112CH″cH2H(X:
H30H3Co2CH2CH2tclH0CH3C2H
5Co2・', HCC, H3>2HOCR3C2H3c
O2('h2)2”H3HQC2II5 °H3C
O2c2H5H0CH3C2115Co2CH3 H0CH3(,H,CI HQC211,CI(3Br H(]C113C21155o2C1i3H0CR3C
2H5So2(CH2), CH3CH30CH3C2 engineering
l5SO2G112CH(CB3)2cH,O(:1(
3C2H,sc,or3CH3QCH3C2H5So2
ZH. CH3,0CH3C2H,5 (r2C1l. CH30CH3C,,)15 0C2H5CH3QC
;H3C211,F CH30CH3C2H5F CH30CH3C2H5SC2H. CH3QC2H, CH35c, 2N(OCH,)CB. CH3oc2n5CH3so2n(CB3)((CH2
)2CH or CH30 (:2H5°H3H )11 R1+ R2° R18! ! ! J Midori
2) Add 2H5CH3N to C1i30. CH3QC2H5C) (3□~:t'2:+H(CH3
)2CI, QC2H, OH3:02trI:2cH
=CH2CH,QC2H,CI+3・2082CH
2CICI, (X:2H5CH,CH30H3Q
C2H5CH3CH(OH3)20H3QC2H50H
3H2Gn(CH3)2C113(X;2H5CH3
□3 CH30C21(,' CH31s02CH. GH30C2H5C) i3CI CB3 °C2H5CH3C2H50H3oc2H
,Cl5No2 CH,0',2H5 to H3Br OH3di2H5CH3°1 C,H3QC2H5°2H5CI C:H30C2H5°2H5Co2. C:H3C113
0G,, H5C convex 5o2CH3CH30C2H5C2H
,5O2N(CH3)2)IOC2H5C2H5N02 HQC2)15C2H5Br IIOC2H5C2H5C02CH(CH3)2h・
R yo ° R2 ° 絠に崣H0 Town
C21+5 S02"2H5H0CH3C2'rr
5F II O',,R5I:H3at:+((':n3
)21(0″:2H5′;R55r2(-H2)2CH
5I 0C2H5C)i3S02CIl(CH3)
2HQC2H5Cl, 502N(02H5)2/
″′ Table 17 (:H3■IC2H5′?′C2°it3CH3CM3
°2H5Br CH3C)13 =2H,”]()R2)
i (CH3)2CI3(J(5C2H5No2 CH3 Town v2H5H Cl3CI3C2H5C1 (:1(3CB3 °2H5CI CH3CH3C2H5CO2CII2"H"CH2C
H3CH3C2H3C○2C; H2CH2ClCH3C
H3C2H5CG2'; h3 CH3CH3j Yu2H, S02 H3 cH3C2H5°H3S02CH3 CH3C2H5CH30 gate CH3'CH3C2H, 5o2N (open 3) 2CH3 di
C2H5N02 CH3CH3C2H5! So2N(CH3)OCR3I
l+ 1?1° ”2’ kV18
! ! J fan)C113°2H5CH3Su2(:
H3CH302H5f;)i3Sc2C:kL3CH3
C2)i, CH3Br cH30H3C211,Br CH30H3°2H5CI CH2O,,H,62H5Br CH3Cl, C2H3Co2CH3H,,C2H
5C2H5S'-2CH3HC2H3C2H5S02N
(':H3)02H5H, CH3t:2n5' 5o2
(CI2)2cH31(C2H50H33CH3 HC2H5C2H5SO2C113 HC2H5°2H5QQ2CHy H02H5°2H5H H'PH3q2n, H HCH3C2H3H HC2H3CaH,5o2N(OH3)2HC2H3C
2H,Br HCH3C2H3F HC2H,62H5F H8CH36H3Br 8° ゝ Iilo R2° R1ε
-is-)H5CH3CIi3Br H5CH3CH3'Br H5CH3CH3H H5CH3CH3':I H5CH3CH3No2 H-)CH3CH3,,S(2N(CH3)"2115
HSCH3CM3S○2N (town) (c dew 13) 2) CH
38CH3°H3F CH3SCH3CH3, H CH35CH3CH3H CH35CH3CH3H CH38CH3CI13S02CkL3CI3SCH3
CH, Co2°H5 CH3SCH3CH3So2N(CH3)2CH3SC
H3';It3 °'''-5CH3SCH3°H3
H CH33 town OH3': o2 (ri I2) 3'
H3CH3SCH3°H3CO2cH2°H2c)CI
(3an3.5C)L, °IL3H CH3SCH3CH30CH (0M3)C2H5CH3
SCH3°H3CH3 1゛° Town "p' R18yo fan and) CH3SC
H3°H35CH3 CH3SCH3CH35(Cn2)3CH3CH3SC
II3 ri2H55O2C2H5CH3SCH3°
H3C2CH(CH3)2cH3SCH3CH3Co
2CH2CH”CH2CH35CH3C2H5Co2C
B3 CH3SCH3°2H5Br CH3SCH3°2H5SC42CH3CH3,5CH
3C2H5CI CH3SCH3C2H, No2 HOCH3CH3C02°H3 H0CH3CH3So2N (C13)C2H. H0CH3CH3Br H0CH3CH3CI HOCH3CH3NO2 H0CH3CH3SG2CH3 H0CR3°H3SO2cH3 HO°H3CH3St, 2CM3 1■0CH3cH3So2(CH2)2CH3HO°H
3°H3°CH3 HOC2H5cH30(CH2)3CH3h' R
1'R2" RI8 5 cancer) HOC2
H5CH3CQ2C)I2CH″CH2H0CH3CH
3 prompt 2C1 (2CH2CIHOCH3C2H5 luster 2CH
(CH3)2■10cH3C2H5CO2(CH2)2
CH3HOC2H5CH3CO2C2H5 HOCH3C2H5CO2CH3 H0CH30,,1(5CI H' QC2H5°H3Br HOCH3C2H5s02cH3 HOCH3C2H5So2(CH2)3CH3CI30
CH3c2n, 5o2CH2CH(CH3)2C
H30CH3°2H5S02°H3 0H3°0H3C2H5So2CH3 CH3, OCH3°2H, So2°H3CH30CH3
C2H5QC2H5 CH3°C) 13 °2H5F CH30CH3C2H5F CH30CH3C2H5SC2H5 CH3QC2H5, CH35o2N (OCH3) CH3
CH30C2H5CH3SO2N(CH3) [(CH2
)2CH3]CH3oc2H56H3H R' BA1° R2° R18YUMCH3(JC2
H,'CH3No2 CH30C2H5cH3CO2cH (to H3)2CH3
QC2H, CH3GO2CH2CI=CH2CH3QC
2H, CH3C2HM2CH2CICH3QC2H5C
H3CH3 CH3:)C2H5CH3cH(CH3)2CH30C
2H5CH3cH2CH(CH3)2CH30C2H5
CH3°H3 CH30c2H5°H3SO2CH3 CI30G,, H5CH3CI CH, QC2H5CH3C2H. CH30G,,H5CH3No2 0M30C2H5°k13Br CH3QC,H5CH3CI CH302H5C2)I5CI CH30C2H,C2H3Co2CH3CH30C2H
5C2H5SO2CH3CH30C2H5C2H5S0
2N(CH3)2HQC2H5C2H,No2 HQC2+(5C2H5Br HQC2H,C,7150020M(CH,)2R”
R1' R2° 1185ge! H0CH3C,
J5SO2C2H5 H0CH3C2H5F HQC2H5, CH30CII(CH3)2CH3QC
2H5CH3502(Co2)2cH3CH3QC,H
5CH3So2CH(CH3)2CH30C2H5CH
3SO2N(C2H5)2♂di♂CH3I C2H3Br CH2CH2O,, H3P CH3C2H5°H3H CH3°2115 6H3No2 CH3C2H5,CH3CH3 CH3CH3C2H5CI CH3CH3C2H5Nc2 CH 3CH3C2H5NO2 CH3C2H5CH3CI CH3C2H5CH3No2 CH3°2H5CH3C1 0H3CH3CH3F OH3°2H5°2N (5H CH3C♂5 °H35o2N(CH3)2CH3C
H3°Z5 E'02CH3C5CH3C,! )1
5802(CH2)CH3''' R11R2°
"14 b" Yu) C2H5E, H5SO2C
2H. C2H5C2H50S02°H3 C2H5°2H5N02 02H5°2H5°l CH3C2H55O2N(CH3)C2H5HCH30
2H5H HCH3C2H,H HCH3°2H5N02 HCH3°H3':H3 H5C113CH3H H5CH3CH3No2 H5CH3CH3CI H5CH3CH3H H3°H3N02 HSCH36H3CI H5CH3CH30CH3 H5 CH3CH3CH3 H5CH3CH3F H5CB3 °H3H HSCH3CH3CI H8cH3cH3NO2 8° R1' R2° R14! ,,-yu)H
5CH3C2H5,CH3 I '5CH3C2H5No2 H5CH302H5H CH3SCH3C2) r50S02CHC12CH3S
CH30H30502°H2°HFClCH35CH3
CH,0502CH(CH3)CH2FCH3SCH3
CH30SO2(CH2)3BrcH3SCH3CH5
0S02(CH2)2CHC12CH3CH3C2H5
,O8O2CF3CH3CM3C2H50802CF2
6H2FOH3C2H5, C2H50SO2C112C
F3CH3SCH3C2H5oS02CHF2CH3C
H3°2H5°5o2CCI30H3SCH3CH3F H0CH302H54 H0CH3C2H5,H H0CH3CH3H H0CH3CH36C1 l(CCH3C2H5s02N(CH3) [C) I(C
H3)2]HoCH3C2H5502N(CH3)[(
CH2)2CH3]H0CH3C2H,5o2N(CH
3) 21° R1'R2° "14 -H) H
OCH3C) [3,03O2(CH2)2Hc12H
0CH3CH3CIS02':H(':113)CI(
F'21i 0CH3,CH30So2CHFCF
3H0C2H5CH3Br HQC2H5CH3CI HQC2H,CB3H HQC,,H5CH3H H,QC,B5CH3No2 HO'C2H50B3SCH3 HQC2H5CH3sea2cn(CH3)2I
0C2H,CH3S(0M2)3CH. H0CH3G,,B5.5(CH2)2CH3HOCH
3°2”5”￥5 HOCH3C2H5S02CH2CH(CH3)2CM
3 GeH4C2H55o2CH(CH3)2C
H3 times 3C2H5S02CH3 CH30CH3C2H5S02(CH2)2CH3HO
CI(3C2H50s02CH2CH20CH3HOc
2H5CH30S02(CH2)30CH3H'
5CH3CH30802 (town) 3CH3HSCH, CB
5Br 1° R11R2° R1421) H5CH3C
H3Br H5CH30H3H Ha 5CH30H3H H5°H3CH3S, >2CH3 H5CH3CH3So2C2H5 H',, OC2H56H, CI HOC2H5°H3NO2 'HC2H5C,! 1 (5H H5CH3CI3CI HDC2H5CH30602CH2CIHOc2H5C
H3S02CH3 u oC2H5CH35O2(Cu2)2CH3)
i QC2H, °H3Sα3 HQC2H5C)L, 0802CF3HOC2H
9CH5SO2N (CIL5) ((CH2)2CH3)
HCM3CH3So2N(OCH3)CH3I C
CH3CH35o2N(QC)B3)CH. HSCH3'CI3. , so2N(OCH3)am. CH3CH3CH35o2N(OCH3)CH3CH3
0CH3CH3S02N(OCH3)CH3CH30C
H3CH3S02N(OCH3)CB3 Preparation Useful preparations of compounds of formula l may be prepared in a conventional manner.
. They are powdered octopus, grain wound, elixir, →1 agent, emulsion, and hydration agent.
, concentrated emulsion, etc. Many of these can be applied directly
can. Sprayable lil products can be bulked up in a suitable medium.
, a spray volume of several liters to several 6 liters/hα is used.
nru. Generally speaking, the preparation contains 0.1-99% of the active ingredient.
% by weight, and α) about 0.1-20% surfactant, and b)
At least one solid or liquid diluent from about 1 to 95L9%
contains. Furthermore, the proportions shown in Table VI of these ingredients are added to the preparation.
It will contain: 19th Table Amount %1 Active ingredient Diluent Surfactant Wettable powder 20-90 0-74 1
-10 (including concentrated emulsion) Aqueous suspension 10-5040-84 1-2
0 powder 1-25 TO-990-5 granules and tablets
Agent 0.1-95 5-99.9 0-15 High strength
degree composition 90-99 0-10 0-2 pieces
At least 1% of active ingredients and surfactants or diluents = 10
Of course, low or limited amounts of active ingredients may also be used depending on the intended use and purpose.
Active components of surface activity that exist depending on the physical properties of the compound.
A high ratio to minutes is particularly desirable, l! # Mixing into products
The process is accomplished by mixing in a tank. Representative solid diluents rJ, Watkins
) et al., “Handbook of In5ec”
ticideDbst Diluents and C
``Arriers'', 2nd edition, V-Ran Y Putx Co., Ltd. (1
) orland Books. Caldwell, N. J.), and others.
Solids, both natural and synthetic, may also be used. I&layer diluents are also suitable for wettable powders and concentrated powders.
Ru. Representative liquid diluents and solvents include Marsde 7 (M
arsdan l plaster,” 5oLv@sts gs
ide”, 2nd edition, Interscience Co., Ltd.
rsienctr. N, Y, ), 1, 0.1% as described in 1950
The following dissolution #i is suitable for concentrated suspensions;
Preferably it is stable to phase separation at 0°C. “Me
Cstcheon'a Dgtargentsand
MmsLaifigrs An%saL”, Al
AllsLred Psbl, C
orp, /v. J-j% J9 and Siagty and Wood (
Wood), “Encyclopedia of S.
surface Active Agents”
Chemical Publishing Company (Chemicat Pwbl, Co.
, Inc., N. Y. J. 1964, surface activity and its recommended uses.
It shows. All preparations should not foam, cake, or spoil.
Food, (i 哄 = small amount of additives to reduce the growth of microorganisms, etc.)
Add 1! It may contain rlI. Of such a composition! # The legacy law is well known. The liquid formulation is manufactured by mixing each component sonoelectricity. Finely divided solid compositions can be prepared using a hammer mill or fluid energy
Manufactured by mixing in a mill and then grinding normally.
It will be done. , the suspension agent is manufactured using a wet mill process.
See also Litt-Ler, U.S. Patent No. λ
No. 084 to 06]. Granules and tablets are prepared by pre-preparing the active substance.
19 or the spindle method by spraying onto shaped granular carriers.
A back road. See, J, j! ;, Prowning (B
rowing l sound, 'AggLomaratio
n”, CILemicαtEngineerin
g, No. 12144, 147-@ (19671, and
Chatnical En by Ferry
Gineer's Handbook, No. 41, 8
~59 negative, Matsufugrow Hill Co., Ltd. (VC-Graw-H
4ll, N. Y. l., 1963. (For Wenxin regarding the technique of preparation, see for example:
Reference: H, M, Louzl, US Tigff No.
23shi No. 361, column 6, line 16 to tooth 74, line 19 and execution
Example 1O~410 RJ, yvtsuken/tsutsu (Luckenbawgh)
, U.S. Pat.
Line 3 ~, Ivy 7 horizontal 62 ('T and Example 8.12.15.
39.41.52.53.58.132.138-14
0.162~164.166.16? , 169-182
゜H, Gyain and E, Nusri (r(n
vbs Li), U.S.%W+No. 2.891,855
No. 3, column 66 to column 5, line 17 and Examples 1 to 4゜G,
C, ys: y r −q 7 (KL ingman
), “Wand Contrat as a
5cience”, Noyon Willy and Su7
JohnWig-fay and 5on
s, Inc,, N, Y, λ. 1961, 81-96 nails. J, D, Fryer and S, A
, 1/? 7th (Evantt) 4, “Weed C
ontrolHαndbook”, 5th edition, Black
Quell Scientific Publications
(Hla-ckuytlt 5 scientific
Publications. 0xford l, 1968, 101-1034° top
The disclosures of the documents mentioned above are incorporated herein by reference.
,ru. In the following examples, all parts are 9 folds unless otherwise specified.
It is assumed that implementation? 1tll H-1,2,4-triazol-3-yl)-aminoca
Aminosulfonyl, methyl sulfate
80% sodium alkylnaphthalene sulfonate
Thorium 2% Sodium Lignosulfonate
2% synthetic amorphous silica
3% kaolinite 1
3% E-chu, ingredients mixed, crushed in a hammer mill and averaged.
Reduce the n-diameter to less than 50 microns, remix, and package.
Ta. Implementation tl 12 Wettable powder 2-[(5-ethylthio-1-methyl-IH-1,2,4-triazol-3-yl)-ami
Nocarbonyl]aminosulfonyl]methylbenzoate
50% sodium alkylnaphthalene sulfonate
um 2% low viscosity methyl cellulose
2% increase ± 46%
Mix the listed ingredients, coarsely grind in a non-mar mill, and then
Essentially all particles are crushed in an air mill to a diameter of 10 mm.
Exchange below Cron. The product was remixed and packaged
. Example 13 Granules Irrigation agent of Example 12 5% Methushi
0.84-0.42 tm) 225% solids
Slurry containing wettable powder in double cone mixer
Spray it onto the surface of the attargite particles. particle 1e
Dried and packaged. By ability 14 Extruded tablet #-[(5-ethyl-1-methyl-1H-1,2,4-triazol-3-ylfaminol)
Ponyl]aminosulfonyl]benzoic acid methyl ester
25% anhydrous hexathorium sulfate
10% calcium lignin sulfonate
5% Sodium alkylnaphthalene sulfonate 1
% Calcium/Magnesium bentonite 59% above
The ingredients are mixed and hammer milled, then about 12%
Moisten your friend with water. Make this mixture into a cylinder with a diameter of about 3 lines.
This was extruded and cut into a 31-length diaphragm. child
f'L can be used directly after drying or
Dry and crushed into a powder and labeled as US;! Sieve No. 20 (opening 0
．． 84 tm). rice 11 standard fu
Particle cage that stays in Lui No. 40 (aperture 0, 42 tm)
Pack it for one more use.'! I was brutalized
. Example 15 Oily suspension 2-[(5-methoxy-1-methyl-1/no 1.2.4-triazol-3-ylnoamino
Carzanil [aminosulfonyl] is methyl zoate
25% polyoxyethylene sorbitol
Kisaoleate S%
Higher aliphatic hydrocarbon oil 70% of the above composition
Grind together in a separate sand mill to form solid particles of approximately 5 microns.
It was reduced to less than Ron. The obtained suspension was applied directly + JLC.
mirror, preferably enriched with oil or emulsified in water.
It was applied to implementation? IJ16 Wettable powder/V-((5-methoxy-1-methyl-1H-1,2,
4-triazole-3-i/L= + 7 Mi/Karza
[Nil]-2-y Loro Village Zensulfone Ryomid
20% sodium alkylnaphthalene sulfonate
4% sodium lignin sulfonate
4% low viscosity methyl cellulose 3% a
I4Tal is Ito 69% higher
The ingredients were thoroughly mixed. Grind it in a hammer mill and make it into a book.
Qualitatively all particles viooξ are lower than or equal to t after 4
Remix the 1F+ quality and pass through a No. 50 American standard sieve (opening 0.
3 as J and packaged. Example 17 Low grade granules N-4 (s-methoxy-1-methyl-111-1,2,
4-triazol-3-ylnoaminocarbonyl) -
Nl, lvl-tumethyl-1,2-benzenesul
Honamide 1% N,N-trimethylformamide 9% atta
・9 Lugite particles so% (US
(Japanese standard sieve No. 20-40) Dissolve the active ingredient in the solvent and mix with Dapulco/Mix.
1 of the 6 tower liquids in which 1lfAI was applied to the solution to dedust particles in the machine! j
After the fogging is completed, run the mixer for a short time, then add the granules.
It was packaged. Example 18 Aqueous suspension linking agent 2-[4(5-methyl-1-methyl-1H-1,2,4
-triazol-3-yl)aminocarbonyl]amino
Sulfonyl llX fragrant methyl ester 40
% polyacrylic acid thickener 03% Dode
Silphenol polyethylene glycol ether
O,S% phosphate 1) Rum
,% phosphoric acid-sodium
. , 5% polyvinyl alcohol
1.0% water
567%F component'&? % meeting and
Grind together in a sand mill to ensure that essentially all dimensions are
◎Execution 1''19 Solution 2-[,((5-ethyl-1-methyl-1H-1,2,
4-triazol-3-yl
Nosulfonyl] Fezoic acid methyl ester, Natriu gokan
5% water
　　　　　　　　　　　　　　　　　　　　　　　　　
Add directly to 95% Shizuka water while stirring to leave a solution.
Next, I'll package it for the first time. Practical 20 Low strength granules 2-[(5-ethylthio-1-methyl-xH-1,2,4-to-11azol-3-ylnamide)
methyl sulfonyl aminosulfonyl sulfonate
Teru 0.1% Ata I9 Lugite particles
99.9% (US standard sieve 20-40 mesh)
Dissolved in a double cone mixture and
The solution was sprayed onto the dedusting particles in a mixer. 44 of solution
After completion of the reaction, the material was allowed to warm up and the bath medium was allowed to evaporate. thing'
# Naturally cooled and packaged into arrows 7? :,. Implementation area 21 Granules 2-LL (5-methoxy7-1-methyl-1#-1,2,
4-1-riazol-3-yl)aminocarmenyl]a
Minosulfo. Methyl ester 80% lubricant
1% crude lisnin
Sulfone Kenkan (contains 5-20% natural sugar)
10% attapal guide clay
Mix 9% F of the ingredients and add 100 mesh
I crushed it so that it could pass the E-clean meeting. This thing/lik next
In the fluidized bed granulator, the airflow was fully adjusted and the product was 1Mt static.
The fluid is fluidized, and the fluidized material is finely divided into seven parts.
Sprayed. , a recommendation and 4 jets, grains in the desired size range
This continued until the drug was produced. Spout a stops, but water content
Flow until the temperature drops to the level desired by Yuryu, generally 1% or more F.
Activation continued with optional addition of Jp4. ** next
Take out the desired size range, generally 14 to 100 mm.
Sifting of Tsushiyu (1410-149 Bakron)
, and packaged for use.
4-triazole-3-nor) 7 mi/carzanil]
-2-Cuclopenzea sulfo/amide
90% Silica S-Rogel 0.
5% synthetic amorphous fine silica 0.5%
The ingredients are mixed in a hammer mill and ground to form the essence.
All sieves were sieved using a No. 50 US standard sieve (opening o, 3t).
m) 1 to 1tI! Manufactured a substance that meets the criteria. this rich
Further preparations can be made if necessary. Example 23 Irrigation agent/V-[(5-methoxy-1-methyl-1H-1,2,
4-1-riazol-3-yl)aminocarbonyl] ~
rvl, /V/-tumethyl-1,2-benzene
Sulfonamide 90%
Octyl sodium sulfosuccinate O1% fine composition
Silica 9.9%
Mix and grind in a S/Mermill to obtain essentially all
However, particles of 100 microns or less were left behind. substance usa
It was passed through a standard sieve No. 50, and then packaged. Example 24 Irrigation agent 2, -[(5-methylthio-1-methyl-1#-1,2
,4-? rear seal -3-il) Ryo Minoka
Aminosulfonylbenzoinyl methyl ester
40% Sodium Lignosulfonate
20% montmorillonite clay 4
0% The ingredients listed above were thoroughly mixed, coarsely ground with a hammer mill,
and then ground in an air mill to ensure essentially all dimensions.
Particles of 10 microns or less were left behind. The apricots were mixed homogeneously and then packaged. 2-[[(5-ethylthio-1-methyl-IH-1,2
,4-triazol-3-yl J aminocarbonyl]a
Minosulfonyl methyl ester 35
% polyalcoholic acid ester and oil soluble petroleum salt
Mixture of honates 6% xylene
59% hiki component molecule - shishiso
Then, I muttered something in the sand mill, crushed the rice, and everything related to it.
Particles smaller than 5 microns and 7 were crushed. 1st row of products
It can be used, mixed with oil, or emulsified in water.
I could have let him do it. Example row 26 Powder 24 [(5-ethyl-1-methyl-1 H-1,2,4-triazol-3-yl J Aminocal
[bonyl]aminosulfonyl]acid methyl ester
10% Ata Cell Guide
10% phyllite
Mixed with 80% active ingredient caretanosergite
and then put it through a hammer mill and grind it all together
produced particles less than 200 microns. crushed port
Mixed with mamonoketai (C primary pyrophyllite until homogeneous)
. Uses The compounds of the invention are active herbicides. They are all
Complete extermination of all plants in areas to be treated, such as fuel
Around storage tanks, around ammunition depots, industrial storage areas, crazy car yards
, outdoor theaters, around billboards, high arrests, roads and Yokai thief V-koo
Extensive control for pre- and/or post-emergent weed control
The usefulness of the surrounding area is shown. In ponds, the compound is used in crops such as wheat and
It is also useful for selectively exterminating weeds in soybean and soybean fields.
be. The f! e-anatomy can be selective or total
One-time application as a herbicide, coexisting crop stalks, and extermination methods
Weed species, weather and climate, selected formulations, application I4j
The decision was made based on many factors, including the law, the presence of enemies, etc.
Zanru. Generally speaking, the compound contains about 0.125 to 1
The river should be treated with 0 Yu/ha of wax. Koba So, Tong
For convenient use, cut to 1 m with soil 4 and/or low organic matter.
for selective weed control, or for short-term
When only sustainability is a concern, low doses in the range listed above are vF+3.
It will be done. The compounds of the invention may be used with other commercially available herbicides, such as
, triazole, uracil, urea, amide, sophenyl
Ether, carbamate and bivitritulium type #,j
It can be used for one period even when combined with Agent E. The herbicidal properties of this compound have been demonstrated in tests over a wide range of doses.
Ru. The test method and results are as follows. Test A Mehi'/Ba(DiQiC(Lri(Lapl, dog)
Bier (b; chinochtoa, crusgatti
l, oat l Avtnafatrba),
Biskusa (Cassiatora), Morning Glory (Ip
ornoea sp, ), Onamomi (Xαnt le in
8p, ), sorghum, corn, Thai, rice
, Wheat seeds and Cyperus tubers (Cyperus)
rotundus) 17, planted in adult invasive medium and
Chemical 'aJ+! using f
Pre-germination processing was done. At the same time, five leaves (including cotyledons)
cotton, a kidney bean with the third leaflet spreading
Me, two-headed crabgrass, two-leafed goldenrod, two-leaved
Leaf karasmui, 5 noodles (including cotyledons) episugusa
, four 4 (say child 4) morning glory, four leaves (cotyledons)
knmu)'s Ona fir, Shimi's sorghum, Shimi's corn
Koshi, soybean with two cotyledons, rice with three nodes, and wheat with a beak.
, and a 3- to 5-leaf Japanese commonweed! I did ko'Jj4. keeping the treated and control plants in a greenhouse for 168 hours;
The response to treatment was then compared with all control cases.
Visually evaluated. The evaluation method used was 0, i.e. no effect.
The scale from 10 to 10, that is, the maximum effect, was set to 4 standards. accompany
The letter symbols have the following meanings. A = Progressive growth C = Etiolation or stem breakage E = Germination inhibition G = Growth retardation H = Shadow formation effect P = Terminal shoot damage U = Abnormal pigment formation X = Leaf axil irritation and 6Y = 1 tumor bud or flower. Using this method, I sampled Eri and found that it was a cultural compound! ffl meeting table A
Shown below. The tested culture compounds are particularly effective in pre-emergence applications.
A statement indicating good extermination of black-spotted sedge. Shorai is a type of compound
are relatively tolerant to soybeans and 2 to 3 are wheat
I am aware that it is resistant to Table A Compound 8 SCM. Compound 9 SCH. Compound 10 CMkai CM. Compound 11 Compound 12 SCH, CHs Compound @ 14 Compound 15 scH, cH. Compound 16 SCH,CM. Compound'@17 Compound 18 0CH. compound 19 0CH1 compound 20 I compound 21 compound 22 0C1i. Compound 23 Compound 24 00H1 Compound 25 Compound 27 Compound 28 1 Compound 29 SCH. Compound 30 CH1 Compound 31 O 8CH1 Chemical compound 32 Compound 33 Compound 34 Chemical compound 1 1-weight ratio Yu/hα 0.4
．． 0 Post-germinated kidney beans 9c 5
C,91 cotton 5C,902G,
9 Morning glory 5G, 9G
9C Onamomi to 10
9C Ebisugusa 9C9c Hamasuge 90 10
nihishiba 9C9G dogfish tao 9c
Oat sc 9c
Wheat 90 9C
Corn 10 to 9c
Soybean 9C9G Rice 9c 9
C compound 2 5 0.4. 05
G, 6Y 5G, 9G, 61's, 9
G, 6Y0 4C, 9G 4C
, 8G 5C, 9G 4C, 8H9C3G 5G, 9G 3G, 8G4C, 9G
2C, 8G 5C, 9G 2G, 8C gC9G 2G, 9G 2G, 8G2C, 9G
5G 5U, 90 9C sc, 9G 4G, 9GS G e Q
G s G, s G sorghum
9 to 9C: Sato
Japanese radish 9C9 and pre-germinated morning glory 9C9G Onamomi 9H9M Ebisugusa 9c
3C, 9G Hamasuge lOE
10I! d□Mehishiba 6(,',
9G 5C, 9G dogfish
xoE 6, gH oat
6C,9H6G,9H wheat 6C
, 9ti 6C, 9H Tomo a-y7
101! ; 10M soybean
9H3C, 8M rice
IOA' lOE Sorghum
sC, tail sC, 9H sa
Radish I OA,'
1084G, 9G 4(,', 9G9c
5C, 9G9G
2C, 8H9H8M 2C, 9G 2C, TG5C, 902C
,7G 3G,70 2G,30 5C,9H3G,8H 4C,9G 2G,'IG9H2C,8
G 1 oHac', 9H 9H3G, 4M 10E 10B ・6C
,9H5C,9H 6C,9G 5C,9G rice
5G, 9G Sorghum 3C, gG Sugar beet 5C, 9G Pre-germinated morning glory 4C, 8H Onus fir 4G Ebisugusa lG Hamasuge 2C, 6G Crabgrass 2G Golden millet 3G, 6G Oat 3C, 6G Barley 2C, 9G Corn 3C, 9B Soybean l;, 3G Rice 5C,BH Sorghum 4C,9H Sugar beet 1C 5C,9G 9C9C 4C,8M 9C5C,9G2C,5G
ec sc; , 9Gtc
9C2C;, qGj
8G to eHtaMIC2
sc, 800 10A'
5C,9G0 6
G, 9G IC, 3GIC10H5C, 9
H IC6C, 9H6C, 9H 2G 7G, 9HI 0H2G, 3
G 10# sC, 9H
IC984C, eH 3CI OA! 10ils6
6G, 9M 6G, 9#0
6C, 9G 5, 9
G Compound 5 1 Historical use ゛-Total Kg/le α o, i Post-germinated indus bean 9G Cotton sC, 9G Morning glory 2, 8G Onion 8G Ebisu grass 3, sG Hamas r
9G, 9G Black-seed grass 3C, 8G Golden millet 5C, 9H Chirasmui xc, eG Com 1111P9G Corn 3U, 9M Soybean 6C, 9G 〒 A (continued l!p Compound 6 Compound 7
Compound 80,1 0.1
0.12H2(:, 9G, 6Y 4
C, 9G, 6Y0 1
IC, IHOlc, a 〕1
4M0 20
3C,9G0 2CQ OIG,4G O o 1C,3G 2
C2H5C,9Ii 2C,8HOQ
Q OQ Q 10 IC, 5G 2
C, 8ti*H2c, 9G, sX IC, 3G i
Ne s, sG 5G model
Rokosi TU, 90 5G Sa
To l icon - - departure
Memae morning glory 9G O
Onamomi 97f
O Ebisugusa 2C, 8G
Ohhamasy loE
O Mehishiba 2C04G
O Dogfish 3G, 9G O
Oats 2c, 9G
O wheat 2C,9G O
Maize Ic, 9G. l is 3C, 8G
Oine toA;
. Sorghum 3C,9HO Sugar beet
-- 2C, eG 5G 2C, 8H2c, 8H 2CO IC4G 2Q 3B 3G O ICO IG O 0 0 2C, 6G lc, rtt2C, 3M
2A 6G 2 to ? #2C, 6G
2G, 6G rice sC
,sG Sorghum 5, 9G Sugar beet - Pre-germinated morning glory 9G Onus fir 9H Episperum 8G Hamasuge 90 Rockweed 2C, at; Golden millet 5C, 9ti Oat 2C, sG Wheat 9H Corn zC, taG Soybean 9M Rice 10/? Sorghum 2C;, 9H 1f Radish - 10C4G, 9G 0 1o0 2C, 9G 088
3C0 989M -3C,'IG
2C2C tOI! ; IC, 4003C, 5G
1(,',2M 03C・
lf ECO sC, 9G 2C0 2C; , 9G 2G
gac, sc; sc, tH. sc, ru 2c, sh. 1011 5C, TG 5
G4C,9M 3C,9H0 rice
60 2G sorghum
2CO Sugar beet - pre-germinated morning glory a, sG I
c; Onamomi 7a
- Ebisugusa 00 Hamasy 3G O
Crabgrass 00 Golden millet lCIC Oats 00 Wheat 00 Corn 2G, 5G
2G soybean lG
O rice 2 (1'
0 sorghum l(,'
0 Radish - 0 4C,8G o 3t;, sti0 〇 - 〇〇〇〇〇0 3C 0 0 o 2G 2HIC 2 to 1(:' Q IC a A (Continued Compound 17 Compound 18 1 Historical Proportion Yu/ Le α, 05
1/20 germinated ugly 7 grain beans [;
9C cotton lc
ac, 8bt morning glory 1
4C, 8M Onamomi
5C, eG Ebisugusa
1(: 4C,TH2
, -qsr 0
2G, 8G Mehishiba o
2. 5G dogfish
xc 9G oat
0 3G, 9G wheat
o 3, 9cj tomo
Rokoshi lC3L m 97f die
Zu lC6G, 9G combination! 1fJ
19 Compound 201/20
1/20 sc, eG, 6Y 4c;, 9G, 6Y5C, 8
04C, 5H ac, rG 5C, 8H sc 9c 3C, 6H3C, 3G 3C, taG 2C, TG3C, 'IG
3C, 809C9C; OIG 6 T (j sC, eG 2C, 9G ec:, stG 1, 2# rice
0 Sorghum 2C Sugar beet - Clear sprout → 1 Morning glory 0 Japanese fir 0 Ebisu grass 0 Hamas rO Hemlock grass 0 Golden millet 0 Oat 0 Komui 0 Corn lG Soybean 0 Rice 0 Sorghum 0 Sugar beet - 5C,9G hc,9G 5
To, 9G347.9G 2C,9G
4, 9G9C5, 9G 9
2C:, BM 2C, 8H4C;, 5H8H
IOA' 9H3C, 609G
2, 3010I! ;
4G, 9G 2C, 9G2C,
3G QC3G, 6GBC;, 8Hac, g
Noisc, 9ti2C
, eG sG 2C;
, 4G20.8H6G 3
,? 05C,905G,9G 5C,9
H3, 58 3G,? G 01
0A' 1(l
10M5ji, BH2G, 9G 5G,
9H5C, 9G 9c
5G, 9G rice
bc, 9G. Sorghum 2, 5G 4
c, gt; Sugar radish 2C, SG
4C, 9ri departure iJ front morning glory 3G, 3H2G, 6ti Ona
fir IC e
Bigusa 2G Ono
- mass r 0 0 meji
Hiba 9G 1
4G dogfish 0
2C, 6M oat 0
4G wheat OO corn 0 3
C, 8M soybean tH. 4 to 2 to 4, 9M mo
Rokoshi 3C4C, 9H sugar beet
9G No, 4H3G・9
G5c, 9G3U, 9G
9C ec 9c sc et; -9M 5G, 80 5G, 9 (r9G
lag 5G 5C, 9G2G, 4G
5G, 9H4, 9G
5C, 9ti4G, 9# 1ob 5G, 9# 10H 3H9H 1as 1oh; sC, 9H6C
, sM 8, 9G 10E al A (continued) Compound #A24 Ihisemono 24 Lingyo -14'+8'Q/h (1' 1/20
2/5 Germinated Pig Ear 1”7 Mafi 2C, TG, 6Y
5, 9G cotton 3C, TG
5, gG morning glory 3
c, qb 4(,:,90 Onamomi
8Q 2c, 9G epi
Sugusa sC, sM a to
,s#/%-vsr 4G
2C, 7G Mehishiba 3G
,? 0 5C, sG dogfish g
Cec; Oat a(,',eG
9C wheat 5C99G
sU, eG corn “Ic, 8H3U
,9G soybean 5C,9G'
5G, 9C compound 25 (1'!+
7125215 1 /20 9C4c, 9a, 6y 4(,', 8G 4, 4#5C, 9G
3C, BG? G O 5G, 90 3C, ac to 8C g, 8G9C4C;
9C g 9C 2C, 8G 4G SU, 9G 3U, 9C gC3 (7,9G 5G, 9G 3G, 9G Rice 5C, 9G Sorghum 3C, 9M Sugar beet core 50.8M germinated, 411 Morning glory 2, 3M Onion fir 5B Ebisu grass 2C no 1 Masug 0 Mexican grass 0 Golden millet IC Oats 0 Wheat 0 Corn 3, g# Soybeans 1C, 1H Rice 2, 8G Moacon 3C, f3M Sugar beet core 2G, 5G5 C-9b
5 G, 9 (y 5
c* 905C, 9G 3U, 9G
5C, 905C, 9H9
9 to 5c, 9G sc;, taH4 to
,9G9HgHg )1 50.8G 5C,9G 4
G, 9G2C, 8010 & 10
E3C, 506G, 90 4G3C;, 8
8 5C, 9H5C, 91 no 4
,9H3,sG 4G4,9M
10H3C, 9H5G, 90
9M 4C, 9H3, 5H8H
3G, 3H 1log log
1or5c, 9H5G, 9/ノ
5C, 9t! sc, eh 1oA7
10A' compound 26 Usage rate wg/ha 275 Post-germinated indenomatous 2G Cotton IG Morning glory 2G, 5G Onahimi
lH Shrimp grass 3G Normal rO Fish/size 0 Golden millet 0 Oat 0 Wheat 0 Corn 2C;, 3M soybean
2C, 2H Chronic A (continued) Compound 26 Chemical @vA27
Compound 271/20 215
1/200 5C, 9G
6Y 4C, 9G, 6Y0
4C, 8G 2G, 3H2G
4C, 8G l;, 9G0
6G 5H04
Ni, sG3c, e, Ho
4C,906G0
9C2C, 8G0 9Cl; 0 9 to 2C
, 5GOsU, eG 2G 0 9C4G , 9Ge
sc, 9G 4, 9H i
Ne 00 Morocon 2G Osa
Touguikono 00 f: Shaved morning glory 2G
O Onamomi 00 Ebisugusa 00 7.1 Nige 0 0 Mehi
Birch OO Golden millet 00 Oat 00 Wheat 00 Corn 00 Soybean 00 Rice 00 Sorghum oG Sugar beet 00 4G, 9G 5C: , 9G4U,
9 (72G, 9G 4G, 9H4C, 8H 5C, 9G 2L°, 9/
)9H5h 5C, 9G 31nolop;
2, gG5C, 9G
1 to 2G, 88 0 4C, 9G O 2 (,', 9G O lag 3G, 802C, 8HIM
, IA loE 1oE 5G, 98 2G, 9G sC, 9G 2C;, 7G clothes A
<6fc Compound 28 Compound 28 '141J for 1f U/ha 2
/ 5 1 / 20 Germination wave a:y? ': yr-rl 3, 8G, 6
Y 4C, 8G, 6 cotton 4G
, 7G 2C, 2M morning glory
4C, 8 to 4C, 8H Onamomi
3G 2G Ebisugu
2C, 4H1, aG bar rxy
2G, sG 3G Mehishi/
4G, 9G 2G,
7G dogfish ec
3c, shbu J Rasmugi lG, 2G
. Wheat 3U, 9G 3C
,9G Tomo O:=7shi 5,sG
l, 9G soybean IC, 2
HIC) -one compound 29 1 compound 30 0.42 Y ec 2S, 9G, 5Y
6C, 9 to 3C, 8G 2G, 9G 3, 8G 9 to 2G 4G, 9G 2C to 9 IC, WG ec xc, 5G9C2C, 6
11 9C2U, 5C to 5, oG 2C, 5G 10 to 3 40.9G 3C, 'IG rice
5, 9G Morokono s, eG sugar beet 9C departure! PII11 Morning Glory 9G Onamoi 9/f Ebisugusa 2C,'IG Hamasr
5 (-Mehi 7) 3G Golden millet 2c, @G Oat IC Wheat 5C, 9M Corn 5C, 9M Soybean 0 Rice S, 9M Sorghum 5C, 9ti Sugar beet 5C:, 9G tG, 4G 4C;, 9G 2
, 9G3, 9G 10
2C, 6G3C, 9M
--・2 L e 2 Hs Hs b 7! of
　　　　　　　　　　　　　　　　　　　　　　　　　
6G1G 2, 9G
lob;0 1
oE t oEIC4, gG
5G 1C5, 9H2C;, g/1 0 5G, 9G
2C□ gHsC2, 8G
IOH2G, 5G0
9M 1 to 2c, s
G 1oA; eh8
C,9H107! ,' sC, sG volume
c, rG -- Rice 5c, 90 6G,
9G sorghum 4σ, 9G
2C, 9M sugar beet -
-Hatsukaya Punishment Morning Glory 9H9G Onamomi 9M 9
11 Ebisugusa 3, 90
2G, 8G Hama 7. 't' 10 g
101j; Mehishiba
3G 2, 6G Dog Bee R-9
#3, 9# oats
2, 9H2C, 8G wheat 2
, 9M O corn 2G
, 9G 9B soybean 9H
9# Rice Iam 9
M sorghum 9HIC, 5G sugar goose
Con--6C, eG
2C;,7G'y,C,taG
2C, 5G8H0 9H0 8G. 10A' O lc 5G 2C, 97f O IC, eG 0 1c, BG. 2C, sH2C 8H0 9H0 2G, 88 0-〇Test B Fertilize and add lime to two plastic bulb pans.
7 tons of falci (FaLlayingto%) sink
I cleared the muddy loam soil. In one pan
Sorghum, Sorghum, Kentucky Bluegrass (K
estsccy blue-gLass) srs species
Various herbaceous plants were planted. In the other pan, add cotton and daikon.
, Hamas 'y' (Cyparua rotsndxs
) Broad-leaf weeds of the craftsmen. The following herbaceous plants
I planted some broadleaf weeds. Mehishi/Parable (Digitali)
αaangwinaLia), dogfish x (Echi
*oeloacrsagaH4), oat (levm
na fatsα), John Nongrass (Sorgfs
m haLgpanaa), dallis grass (Pasp
aLsm dilatatum), Oeno=togusa
(Sataria fabarit), Suzumetsucha
≠Hiki (Bromsa 5aeaLsssa), Kara
China (Brasaiaa ar palm-3sg), Onamo
i (Xanthixm pgnnaylvanicu
m), Atnarant#us ratr
ofLezus), Asagao (Ipomoea he
dttracttα), shrimp 4gusa (Caaaiato
ra), Tearai-4 (Sidα, 5pinosα
), Abxtilon thaop
hrasti), Datu (Datu)
ra strannium). In addition, two pots with a diameter of 1150 II are filled with pre-prepared Ueki warehouses.
n. I planted rice and wheat゛. To other IZ5cR sisters
I got 1r44i of sugar beets. , four containers on the back
Pre-emergence treatment with several test compounds falling within the scope of the invention
did. After 28 days of treatment, the evaluation system described above in Trial A was used.
In fact, Eli is able to see plant responses to chemical treatments with the naked eye.
Evaluate your friend. This data is shown in Table B. Preparing the tank
#J is for pre-emergence treatment of weeds in crops such as soybeans and wheat.
It turns out to be useful. Tsu-φ j D ■ ■ ＼ TWR”ki Tsuta ← mo
Beyamta layer
! :! takushu −ψ n
Me ψ n 啼 to --N to
ー＠ ■ h60 ■ ■ −ψ
Tsu Tsu :+) 1
℃■ cIJ
−'s award 艷 (he h
l(lto 7 toma iro
Lo lo lo. ◎. Lo lo lo. 0. Keyakiya~! Hero lo lo lo lo lo lo lo
lo lo lo lo (thi X
H-:% sound ＼ pe 1-5
Ki 1 job mouth ＼
Ri! 1 5 3
bo 啼 ro ro ［F］ ro
lo lo lo lo lo lo lo
Ro 0 Ro Ro Ro 0 Ro
Q33 The legacy is ζ phrase
So--4 flashes 5 1 [F] [F] two
b・ri view 0
-rorororo ωroroichi/ +'l mo ki be 4
' Hair Test C Test chemical vIJ dissolved in a solvent that is safe for plants.
Senbon on the leaves of selected vitreous species and the leaves around them.
4L rumor 4 was applied to. 1 day after treatment, acute
Observations were made regarding burn +14 wounds. Processing FE 14
The response to the treatment was compared with the untreated control example of all cypress trees.
The answers were evaluated visually. This evaluation system is based on Table 4.
It was as mentioned above. The data are shown in Table C. Seeds of all plant species
own) Fl in sand spit loam soil and grown in greenhouse.
. The following dlI plastic flowerpot (Direct Pole 251
x Depth 13 times
C: Soybean, cotton, alfalfa, corn, rice
Ne, wheat, sorghum, velpet leaf (Absti)
Lon thaop9raati) Sespania (S
asbania aycaLtata), Episgusa
(Cαattia torα), morning glory (Ipom
oaα 8p, ), Datu dea
atramoniutn), Onamomi (Xanth
ism pennsyLvanicum), crabgrass (
Digitalia 5p-), bar qxy (C; yp
8-rss rotundsa), Inupi x (g
chinoch-1oa erssgaLLi),
Sataria faberii
, Avana fatsa
. Paper tip the following stem (diameter 12CWL x depth 13 scratches)
Growing in the soil; sunflowers, sugar beets, etc.
Mustard greens. Spray on all plants about 14 days after planting in the tank.
did. The compounds tested in this method are highly active post-emergent herbicides.
Met. n) to mame ψ
tsux 0 3 0 ji 33! ”!333
Bird ゞ. ψ A% &”(+' H to compensation to cram school
Screen Fu λ■ −−〇 Φ ■ ■
-■ Continuation of the first page in --■Int, C1, 3 identification code Internal serial number (C
07D 401/12 13100 249100) Priority claim @July 10, 1981■United States (US)■
282174 @ May 28, 1982 Φ United States (US) ■ 382711 @ June 1, 1982 ■ United States (US) ■ 382877 0 Inventor Anthony David Wurtz America
151 Kirkcaldy Drive, Elkton, Maryland 21921 0 Inventor David Joseph Fidgeeral
West Grove R.D. 2 Box 91 Bee, Pennsylvania, USA 19390

Claims (1)

[Claims] 1. Formula [wherein R1 is 6% C1-C4 alkyl, C3-C4 alkenyl, C8-C, alkynyl, SRORs, C
Hl ORe, CHtCHtORe, N<CHs lt
, CFs , CFtCFs , CI, NHCH, , R
5 is C, -C, alkyl, C3-C4 alkenyl, C8
~C4 alkynyl, CH, OCH3, CHt CHt
QCHs, CHt SCHs, CHt CHt 5
CHs or C1-C4 alkyl substituted with 1 to 3 F atoms; R3 is H or CH; R4 is C1-C4 alkyl, C3-C, alkenyl, C
3~C, alkynyl, CH2C01Re or FiCH(C
Hs l C0tRe; Rs is C3-C, alkyl% C3-C4 alkenyl, C3-C4 alkynyl, C
Ht COt Rs, CH(CHs l COt Re
or CH, CF3; R6 is C1-C, alkyl; Will, O or S; R1 is H, Ct-C4 alkyl, C5-C4 alkoxy, F, C(01NR□Rtt, CI, B ",No,,C
Fs, C0tRo, 5OtNR+aRtt, C(0
18R+. , So, N(OCHslCHRlQ, SOz
R1! , S (0)nRts , CHt Cot
Rto, CH(CHsIcO, R10, CHtS(0)
nRts, cH(CH,l S (01°R,,,C,
C2-C, alkyl or 311-5 C1% B substituted with either ~C, alkenyloxy, C1-C4 alkynyloxy, QCH, or 0CtHs
r or FiF atom or b l 0CHs or 0C
is C3-C3 alkoxy substituted with IHs; R3 is HsF%Cl%BrsCFs
, NO! , C, -C, alkyl or C0-C, alkoxy; Ro is Cl" C6 alkyl, CH, CH, OCH3,
CHt CHt OCHg CHs , CHp CH2
CH2QCH1CH3, C, ~C6 alkenyl, C3~
C6 alkynyl or C2-C3 alkyl substituted with 1 to 3 CI or F atoms; RIQ and Run
independently C1-C3 alkyl: R, tdC, -c, alkyl, CH2CH,0CH1,
CH, CH, cH, OCHs or C0-C4 alkyl substituted with 1 to 3 F, CI or Br atoms; all are C, -C, alkyl, allyl, 1 to 5 F
, CI or Br atom; n is O, ] or 2; Q is O or NCH; RI4 is H, Cf(5, OCH,, F, CI, Br No, SOx NR, o Ru 1%5O2N (O
CHs ) CHs, 08O7R+ or 5(0)nRt
s; RI R is H, CI, [3r, CHII
, 0CHs or NO; RIQ is H, C, ~C, alkyl, CI~C, alkoxy, F s Cl s Br s CF 3% C02
R*o, 5OzNRto Rtt, 5OtN (OC
Hs ) CHa or 5(0)Rus; R17 is H% F, C1% Br, CH, or QCR
3; W' is 0 or S; R58 is H% C5-C4 alkyl, C9-C4 alkoxy, F, CI, Br% N Ot, C0
tRto, So, NR,. Ru, 5OtN(OCHs
lCHx or 5(0) Rus; R+ o Fi Cl -Not , CFCo, R,
,5OzN (OChal CHa ,5OtNR+o
Ru, QSO*R+*, S (0)nRts or 1
C7-C3 alkoxy substituted with ~5 CI or F atoms; R8° is C, -C, alkyl, CH! CHt OCH
*, CHt CHt Cl or CH, CH=CH, and R□ is C1-C3 alkyl or Cs Hs;
R□ is C3-C, alkyl, and can be, with the proviso that the total carbon number of Rto and R11 is 4 or less, (21R, and the total carbon number of Rt is 6 or less (3) When W' is 0, R18 is HlCl
, Br, CH3 or Co, R,. and (4) W
' is O, and RI8 is H, CI, Br or CH,
16) When Ry is H, R8 is H, and (7) RI4 and R4i cannot both be NOl. 2. Formula [wherein, R' is H%CH, and C*H5; R5
' is CHs, C*Hi, SCH OCH3 or 0C
IHs; R2' is CH3, C1H! ! or ocas; Z'
R1 is C3-C4 alkyl, C9-C, alkoxy, F
-CI-Br%Not, CF, , CH, CO, R,. ,
CH(CH13CO,R,.,CHtS(0)nR
+s, CH(CHs)S (OlnR+s, C3~
C4 alkenyl f--, C3-C4 substituted with C3-C4-rukynyloxy, OCH3 or OCt R5
, alkyl, or a11~5 C1%Br or F
Atom or b) OCH, tonshi Fi OC! C1-C3 alkoxy substituted with any of H*; R8 is H, F, C1% Brs CFs, NOt, C
1-C, alkyl or C1-C, alkoxy; Ro is CI-C6 alkyl, CH, CH, OCH,, C
H, CH, OCH, CH,, CH, CH, CH, OCH
, CHq, C3-C6 alkenyl, C3-C6 alkynyl or C1 substituted with 1 to 3 CI or F atoms
~C, is alkyl; Rlo and Rol are independently C1-C3 alkyl; R1! is C1-C4 alkyl, CH, CH, OCH
Ht CHt CHt 0CHs or 1-3 F%C
is C1-C4 alkyl substituted with I or Br atom; RI is C1-C4 alkyl or allyl; RI4
is H%CH,, OCH3, F%CI, Br. No, ,So,NR,. R1S Ot N (OC
Hs l CH*, O20,R, or 5(0)nR,
S; R1, is H% CI ~C, 7/l/*
/l/, c, ~c4ryukoxy, F, CI, Br,
CF3, Co, R2o. 5O2NR4oR++, So, N(OCH, lcH% or 5(0)nR,,,; R1, is Hlc, ~c4 alkyl, C, -'-C, flukoxy, F', CI, Br, No,, Co,R,.,8
0, NR, oR, , SO, N(OCH3)CH, or S (01nR,,; R7° is C5-c4 alkyl, CHt CHt OCH
*, CH2CH, CI or CH2CH=CH, with f;
Q is 0 or NCH; R2 is C1-C3 alkyl or Cn H! It is l;
R□FiC, ~ C3 alkyl, and can also be, under the conditions of ill R,. and R7, the number of carbon atoms is 4 or less, and f21 R,' and Rt' cannot be H at the same time] and their agricultural use. 3. The compound according to claim 1, wherein W is 0 and R3 is H. 4, 2, W' is S; R1, is Co, CH,,5o2N(CH3) or tiS
3. The compound according to claim 3, wherein R15 and R1 are H. 5. The compound according to claim 4, wherein 2 is. 6, R1 is C1-C, alkyl, SR4, OR5, CH
*0CHs, N(CHs It is also FiCI; R
1 is C1-C, alkyl, CH, CF8, CH, CH=
CH. or CH, C═CH, and R4 and Rs are independently CH3 or C,H. 8 R1 is other than H, and R1 is H, F%CI%Br, CF3, CH3 or OCH
, t, the compound according to claim 6. 8, R1 is C1, ONt, C0tRo, 5OtNR
+o Rat or OS O* Rt t; R3 is H; R9 is C1-C, alkyl, CHt CH=CHt, C
H, CH20CH, or CH, CH, CI; Rl
7. The compound of claim 6, wherein o and R11 are independently C1-C, alkyl, and RO2 and R13 are independently C8-C3 alkyl. 9, RO, RIIH11, Rl! and R1, is CH3
The compound according to claim 8, which is 10. The compound according to claim 2, wherein R' is CH3 or Ct Hs. where R, is H%F%CI, BI CFa, CI (1 or 0
11. The compound according to claim 10, which is cH3. 12, RydZCl, Not, COtRe
, 5OtNR+ o RII, OS OtRt or 80. R,, with Te; R8 is H; Ro is C1-C, alkyl, CH, CH=CH2, CH
ICf(, OCH3 or CH, CH, CI; R1
12. The compound of claim 11, wherein o and R11 are independently C8-C, alkyl, and Rlt and BI3 are independently C1-C3 alkyl. 13, RIls R1゜, R1-R1, and R1,
13. A compound according to claim 12, wherein is CH3. 14, 2-[[(5-methylthio-1-methyl-IH
The compound according to claim 1, which is -1,2,4-)riazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid methyl ester. 15, 2-[[(5-ethylthio-1-methyl-IH
The compound according to claim 1, which is -1,2,4-)riazol-3-yl)aminocarbonyl]aminesulfonyl]benzoic acid methyl ester. 16, 2-[[:(5-ethyl-1-methyl-IH-
The compound according to claim 1, which is 1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benbrozoic acid methyl ester. 17, 2-C[(5-methoxy-1-methyl=IH-
The compound according to claim 1, which is 1,2,4-triazol-3-yl)aminocarbonyl]aminosulfonyl]benzoic acid methyl ester. 18, N-[(5-methoxy-1-methyl-IH-1,
2,4-)riazol-3-yl)aminocarbonyl]
The compound according to claim 1, which is -2-chlorobenzenesulfonamide. 19, N-[(5-methoxy-1-methyl=IH-1,
2,4-)riazol-3-yl)aminocarbonyl]
-N',N'-dimethyl-1,2-benzenedisulfonamide, the compound according to claim 1. 20, 2-[[(4,5-dimethyl-IH-imidazol-2-yl)aminocarbonyl]aminesulfonyl]benzoic acid methyl ester, Claim 2
Compounds described in Section. 21. An effective amount of the compound according to claim 1 and at least one of a surfactant or a solid or liquid diluent.
A composition for inhibiting undesirable plant growth, comprising seeds. 22. An effective amount of the compound according to claim 2 and at least one of a surfactant or a solid or liquid stimulant.
A composition for inhibiting undesirable plant growth, comprising seeds. 23. An effective amount of the compound according to claim 3 and at least one of a surfactant or a solid or liquid diluent.
A composition containing seeds for inhibiting undesirable plant growth. 24. An effective amount of the compound according to claim 4 and at least one of a surfactant or a solid or liquid diluent.
A composition for inhibiting undesirable plant growth, comprising seeds. 25. An effective amount of the compound according to claim 5 and at least one of a surfactant or a solid or liquid diluent.
A composition for inhibiting undesirable plant growth, comprising seeds. 26. an effective amount of the compound according to claim 6 and at least one surfactant or solid or liquid diluent;
A composition for inhibiting undesirable plant growth, comprising seeds. 27. An effective amount of the compound according to claim 7 and at least one of a surfactant or a solid or liquid diluent.
A composition for suppressing undesirable plant growth, which contains seeds. 28. An effective amount of a compound according to claim 8 and at least one surfactant or solid or liquid diluent.
Composition 829 for suppressing undesirable plant growth containing ridges, characterized by applying an effective amount of the compound according to claim 1 to the area to be protected. A method to suppress undesirable plant growth. 30. A method for suppressing undesirable plant growth, which comprises applying an effective amount of the compound according to claim 2 to the site to be protected. 31. A method for inhibiting undesirable plant growth, which is characterized in that an effective amount of the compound according to claim 3 is applied to the site to be protected. 32. A method for inhibiting undesirable plant growth, which comprises applying an effective amount of the compound according to claim 4 to the desired location. 33. A method for suppressing undesirable plant growth, which comprises applying an effective amount of the compound according to claim 5 to the site to be protected. 34. A method for controlling undesirable plant growth, which comprises applying an effective amount of the compound according to claim 6 to the site to be protected. 35. A method for suppressing undesirable plant growth, which comprises applying an effective amount of the compound according to claim 7 to the site to be protected. 36. A method for suppressing undesirable plant growth, which comprises applying an effective amount of the compound according to claim 8 to the site to be protected.