JPH01311058A - Aryl, pyridyloxyurea compound and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I [Q1 and Q2 are group shown by formula V (R1-R5 are H, halogen, trifluoromethyl, etc.) or group shown by formula VI; R6 and R7 are H, 1-6C alkyl, 1-6C alkenyl, 1-6C alkynyl, etc.; X is O or S]. EXAMPLE:3-(3,5-Dichlorophenoxy)-1-methyl-1-phenylurea. USE:An agricultural and horticultural herbicide. PREPARATION:An aryloxyamine or pyridyloxyamine shown by formula II is reacted with a carbamoyl halide shown by formula III' in the presence of pyridine, triethylamine, etc., in a solvent such as THF or acetonitrile to give a compound shown by formula I''. Then this compound is reacted with an electrophilic reagent shown by formula IV in the presence or absence of pyridine, etc., in a solvent such as THF or in a solventless state to give a compound shown by formula I'.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel aryloxyurea compounds, pyridyloxyurea compounds, and selective herbicides and plant growth regulators containing these compounds as active ingredients.

[Conventional technology and issues]

Currently, many herbicides have been put into practical use as herbicides for paddy fields, and are widely used as single agents or mixtures.

There are many types of rice field weeds that can be targeted, and many herbicides that are effective against -year-old broad-leaved weeds are known, and the number of herbicides that are effective against perennial weeds has been increasing in recent years.

However, because Noviae, which is one of the important weeds in paddy fields and has the largest infestation area, belongs to the same family as rice, Poaceae, it does not cause any chemical damage to paddy rice and is highly effective against Noviae, especially on mature plants. Very few herbicides are known.

[Means to solve the problem]

As a result of repeated studies aimed at improving the above-mentioned problems of conventional herbicides, the present inventors found the following general formula (■): [In the formula, Q and Q2 each independently represent the following.

R,, R,, R,, R, and R3 are each independently,
It represents a hydrogen atom, a halogen atom, a trifluoromethyl group, a difluoromethoxy group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms.

Rh and R1 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms, or 1 to 3 carbon atoms.
Number of carbon atoms, which may be substituted with an alkoxy group of 1 to
2 alkyl group, an alkyl group having 1 to 2 carbon atoms which may be substituted with a thioalkoxy group having 1 to 3 carbon atoms, and a carbon which may be substituted with an alkylamino group having 1 to 3 carbon atoms. Alkyl group having 1 to 2 atoms, 3 carbon atoms
~6 cycloalkyl group, a benzyl group optionally substituted with a halogen atom, a benzoyl group optionally substituted with a halogen atom, a carbon atom optionally substituted with a cycloalkyl group having 3 to 6 carbon atoms Number 1~
2 alkyl group, C(0) Rs group (wherein R@ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms), -5(0)zRq
group (wherein R1 represents an alkyl group having 1 to 3 carbon atoms or a phenyl group which may be substituted with a halogen atom or a methyl group), 5(0)! NRII (R9) group (
However, R11 and R9 have the same meanings as above. ),
or -C(0)N(R8) (Rq) group (wherein R8 and R9 have the same meanings as above), or R1 and Q! may be connected by an alkyl chain having 2 to 4 carbon atoms (,
The aryloxyurea compounds and pyridyloxyurea compounds represented by X represent an oxygen atom or a sulfur atom have a high herbicidal effect on field weeds and other paddy field weeds, and are highly safe for paddy rice, and are easy to use as chemicals. The present inventors have discovered that the amount is small and the toxicity for human storage is extremely low, making it safe and has led to the completion of the present invention.

In addition, some of the compounds of the present invention had a growth-regulating effect on plants, and in particular, a remarkable growth-inhibiting effect on wheat was observed.

It has been known that aryloxyurea derivatives and pyridyloxyurea derivatives have herbicidal activity;
No. 0353 discloses N-alkyl-substituted aryloxyurea derivatives, and JP-A-62-277358 discloses N-alkyl-substituted aryloxyurea derivatives.
-Alkyl-substituted pyridyloxyurea derivatives are disclosed.

However, N-aryl-substituted aryloxyureas, N-pyridyl-substituted aryloxyureas, N-aryl-substituted pyridyloxyureas, and N-pyridyl-substituted pyridyloxyureas such as the compounds of the present invention are not known at all.

The compound (1) of the present invention can be synthesized by the methods shown in the following reaction formulas (1) to (4).

To the antibreath m (n) (III') (
1') R& [In the formula, Q+, QZ, R&, and Rt have the same meanings as above, and Hag represents a halogen atom] That is, aryloxyamine or pyridyloxyamine (n) is replaced with pyridine, triethylamine, DBU, etc. In the presence of an organic base or an inorganic base such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium hydride, etc., in a solvent such as tetrahydrofuran, acetonitrile, DMF or without solvent, the present invention A compound (■#) that is a part of a compound can be synthesized.

Furthermore, compound (I") is pyridine, triethylamine,
Electrophilic reagents ( T
By reacting with V), compound (1'), which is a part of the compounds of the present invention, can be obtained.

As an electrophile, R+allaj! (However, R.I.G.
is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms. 1-2 carbon atoms optionally substituted with an alkyl group having 1-2 carbon atoms or a thioalkoxy group having 1-3 carbon atoms
an alkyl group having 1 to 2 carbon atoms, which may be substituted with an alkylamino group having 1 to 3 carbon atoms,
11a represents a cycloalkyl group having 3 to 6 carbon atoms or a benzyl group optionally substituted with a halogen atom;
2 has the same meaning as above, halogenated alkyl represented by R,, C(0))Iaf or [R+ +C(
0) ) 20 (However, Ro represents an alkyl group having 1 to 6 carbon atoms or a phenyl group which may be substituted with a halogen atom, and Hal represents the same meaning as above.) Acyl or carboxylic acid anhydrides, formylating agents such as formic acid-acetic anhydride, Riffi'11C(0)C
j! (However, R1! represents an alkyl group having 1 to 6 carbon atoms.) Alkyl chloroformate, p*5OzH
sulfonyl halide, Rs (Rs) NS, represented by af (where R,, Hal has the same meaning as above)
Sulfamoyl halide, R1(R9) NC(0) tla l (wherein R,,R,, Haf has the same meaning as above), OtHa 12 (wherein, R,,R,, Haf has the same meaning as above).

Examples include carbamoyl halides represented by (Hal has the same meaning as above), isocyanates represented by R9NC0 (wherein R9 has the same meaning as above), and the like.

(■') [In the formula, Q+, Qz, Rh, Rt, and Hai have the same meanings as above. ] That is, aryloxyamine or pyridyloxyamine (U) in the presence or absence of an organic base such as pyridine, triethylamine, or DBU or an inorganic base such as sodium hydroxide, potassium hydroxide, potassium carbonate, or sodium hydride, N
-Synthesize a substituted aryloxyamine or an N-substituted pyridyloxyamine (V), and convert the N-substituted pyridyloxyamine (V) to an organic base such as pyridine, triethylamine, DBU, or sodium hydroxide, potassium hydroxide, potassium carbonate, Tetrahydrofuran, acetonitrile, DMF in the presence or absence of an inorganic base such as sodium hydride
Carbamoyl halide (m') in or without solvent, such as
Compound (1') which is a part of the compound of the present invention by reacting with
can lead to.

The electrophilic reagent (IV) used in this reaction is R,0
Hal (However, R11+ is an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms.
-6 alkynyl group, an alkyl group having 1 to 2 carbon atoms which may be substituted with an alkoxy group having 1 to 3 carbon atoms, and a carbon which may be substituted with a thioalkoxy group having 1 to 3 carbon atoms Alkyl group having 1 to 2 atoms, 1 carbon atom
Indicates an alkyl group having 1 to 2 carbon atoms which may be substituted with ~3 alkylamino groups, a cycloalkyl group having 3 to 6 carbon atoms, or a benzyl group which may be substituted with a halogen atom, Hai, has the same meaning as above. ) alkyl halide, Rw +C(0)
Ha 1. or (R++C(0)) zO (however, R1
1 represents an alkyl group having 1 to 6 carbon atoms or a phenyl group which may be substituted with a halogen atom, and Hai has the same meaning as above. ) halogenated acyl or carboxylic acid anhydride, formylating agent such as formic acid-acetic anhydride,
R1! QC(0)CI! , (wherein, Rlm represents an alkyl group having 1 to 6 carbon atoms), RqSOJa j! (However, R9+11al
has the same meaning as above. ), a sulfonyl halide represented by Rs(R9)NSO! Ha l (However, RI
+R9 and Hal have the same meanings as above. ) Sulfamoyl halide, Rs(Rw)NC(0)H
a carbamoyl halide represented by a l, (wherein R,, R9, and lal have the same meanings as above), R,
Examples include isocyanates represented by NGO (where R9 has the same meaning as above).

[In the formula, Q+, Qz, R4, Rt, and Hal have the same meanings as above. ] That is, aryloxyamine or pyridyloxyamine (II) or N-substituted aryloxyamine or N-substituted pyridyloxyamine (V
) in the presence of an organic base such as pyridine, triethylamine, or DBU or an inorganic base such as sodium hydroxide, potassium hydroxide, potassium carbonate, or sodium hydride, in a solvent such as tetrahydrofuran, acetonitrile, or DMF, or without solvent. Compound (■#), which is a part of the compounds of the present invention, can be synthesized by reacting with (■').

(! 6 [In the formula, Q+ + Qz, R-r r X, l1
af has the same meaning as above, RI31 and R14 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R13 and R14 are connected by an alkyl chain having 3 to 6 carbon atoms. In other words, aryloxyamine or pyridyloxyamine (II) is added to ketones or aldehydes (Vl) in a solvent such as ethanol, acetonitrile, DMF or without a solvent.
and O-aryl substituted oxime or O-pyridyl substituted oxime (■) is synthesized by dehydration condensation in the presence or absence of a mineral acid such as hydrochloric acid, and further, O-aryl substituted oxime or O-pyridyl substituted oxime (■) is synthesized. (2) is converted into N-substituted aryloxyamine or N-substituted biridyloxyamine (V') by catalytic reduction using a palladium or platinum catalyst or by reagent reduction using NaBH, diborane, etc., and (V')
An organic base such as pyridine, triethylamine, DBU, or sodium hydroxide, potassium hydroxide, potassium carbonate,
(1 '') which is a part of the compound of the present invention by reacting with (thio)carbamoyl halide (III) in the presence of an inorganic base such as sodium hydride in a solvent such as tetrahydrofuran, acetonitrile, DMF or without a solvent.
can be synthesized.

The raw material aryloxyamine or pyridyloxyamine (II) used in reaction formulas (1) to (4) is manufactured by Chemistry and Industry.
dIndustry), page 559 (1962)
, Journal of Chemical Society Perkin I
(Journal of Chemical 5ocie
ty Perkin I) + 1827 pages (1977
Synthesis can be carried out by appropriately selecting the methods described in JP-A-60-169447 and JP-A-60-169446, etc.

Hereinafter, the synthesis of the compounds of the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto.

3.5-Dichlorophenoxyamine Ig containing 3--dichlorophenoxy---1-phenyl and 0.95 g of N-methyl-N-phenylcarbamoyl chloride were dissolved in pyridine 5I112 and heated at 80°C. Stirred for 2 hours.

After cooling the reaction mixture, 30IIIL of water was added, and extraction was performed with chloroform.

The chloroform layer was washed with water, dried with anhydrous sodium sulfate, and the solvent was distilled off.

The resulting residue was subjected to silica gel column chromatography (
Purification was carried out using chloroform as an eluent to obtain 0.1 g of the desired product.

Melting point: 117-119°C Main constituents: 3.5-dichlorophenoxyamine Ig and N-(6
Using 1.12 g of -Medoxy-2-pyridyl)-N-methylcarbamoyl chloride as a raw material, the reaction and operation were carried out in the same manner as in Example 1 to obtain 0.4 g of the target product.

Melting point 109-111''C Using 3,5-dichlorophenoxyamine Ig and 1.03 g of N-chlorocarbonylindoline as raw materials, the reaction and operation were carried out in the same manner as in Example 1 to obtain 0.6 g of the target product.

Melting point: 150-151''C Next, the compounds synthesized according to the above examples are shown in Tables 1 to 3, including the above examples, but the compounds of the present invention are not limited to these.

However, the symbols in the table each represent the following meanings.

Me: methyl i, Et: ethyl group, Pr: normal propyl group, 1-Pr: isoprobyl group, Bu: normal butyl group, 1-Bu: isobutyl group, 5ec-nu: secondary-butyl group, t-Bu: tertiary butyl group,
Pen: normal pentyl 75, Hex: normal hexyl group, QIo-Q'7o has the following meaning.

QIo QI QIIIQ,z
Q,, Qz.

Q l 3 Q I?
Q z I(h 2 Q
z b Q 30Q z s
Q z v Q 31Q z
4 Q 28 Q s
zQ 2 S Q z q
Q 33p
MeC! Q 34 Q 3 @Q a
zQ,, Q3.
Q, KoQ 36
Q ao Q
a <e Qko? Q a IQ a
s gate e Q4hQsoQs4 Q 4? Q s +
Q s se Qa*QszQsb Q a q Q S :l
Q S 7Q s m Q &
z Q & bQ S 9
Q h 3 Q h tQ
b o Q h a
Q b sQ6+Q&5Qhv Q? l Qts
Q? 9e Q? -Q--Qs.

Q? 3 Qtt
Qs+Q,, Q,,
Q.

53Qst 5aQss Q s s Q e qTable 1 Q19 HMe
ro1゜Q19 HMe Qll Q19 HMe Q12 Q19 tl
Me Q1
3Q19 II Me Q14Q1
9 II Me Q15Q19
If Me
Q16Q19 HMe Q17 Q19 HMe Q1B Q19 HMe Q19 Q19 II Add Q20Q19
HMe Q21 Table 1 (continued) QI R6R7Q2 Q19 It Me
Ω23QI9 HMe
Ω24QI9 HMe
Ω25QI9 HMe Ω
26QI9 HMe Ω27
QI9 If Me
Ω28QI9 II
Me Ω29QI9
H-Kon 030Q19 t(Me
Ω31QI9
It
Me Ro32Q
19 It Me
Ω33QI9 HMe
Ω34QI9 HMe
Ω35QI9 If
Me
Ω36QI9 If
Me
b37Q19
HMe Ω38QI9 HM
e Ω39Q19 II
Shame 040 Table 1
(continued) QI R6R7Q2 Q19 It Me
Ω41QI9 tl
Me Ω42QI9
II
Me
RO43Q19 HMe Ω
44QI9 It Me
Ω45QI9)
I Me
Ω46QI9
HMe Ω47QI9 HM
e Ω48QI9 II
Me Ω49QI9
HMe Q50Q19HM
e b51019
11
? Se Ω
52QI9 HMe
B53Q 19 I
I Me Ω54
Q19 HMe Ω55QI
9 II Me
Ω56QI9 II
Me Q57 Table 1 (continued) QI R6R7Q2 Q19 HMe Ω59QI
9 HMe Ω60QI9
H shame 061Q19
II Me Ω
62QI9 HMe Ω63
QI9 If Me
Ω64QI9 If
Me Ω65QI9
HMe Ω66QI9
HMe
RO67Q19 HMe
Ω68QI9 II
Me
Ω69QI9 If
Me Ω70QI9
HMe Ω71QI9 H
Me Ω72QI9 H shame
Ω73QI9 II
Me Ω74QI9
II Me
Ω75QI9 It
Me Q76 Table 1 (continued) QI R6R7Q2 Q19 HMe Ω77QI
9 HMe Ω78QI9
HMe Ω79QI9
HMe Ω
80QI9 HMe Q81
Q19HMeQ82 QI9 II Me
Ω83QI9 Me
Me
QIOQ19 Et
Me QIOQ19
Pr Me
QIOQ19 1-Pr
Me QIOQ19 Bu
Me QIOQ
19 1-Bu
Me
B10Q19 5ec-Bu
Me QIOΩ19 t-
Bu Me QI
OQ19 Pen Me
QIOQ19 He
x Me
b10Q19 CH2
Cl1=CIIZ Me
QIO Table 1 (continued) QI R6R7Q2 QI9 CHICMCHMe
010Q19 C0g(1:N
Me QIOQ19 C
HzOCHs Me
Q10Q19 CIIzOCIIzCIIs
Me QIOQ19
CH□0C11□CIItCHs
h QIOQ19 HzC
HzOCHs Me
QIOQ19 CHzCIhOCHzCll+
Me 010 mouth 19
CIIzOCH(CJl3)z
Me QI
OQ19 CHtSCIIi
Me QIOQ19 CH5
HtCII, Me
QIOQ19 CHzSCHzCHxCIIs
Me 010 mouth 19
C1hCHzSC1h
Me QIO
Q19 CToCHzSCHzCHs
Me QIOQI9 CH
tSCH(CJl3) z Me
010Q19 CHzCIIJ(CH
s) z Me QIO
QI9 Cyclopropyl
Me QIOQ19 Cyc
lobutyl Me
Q10 Table 1 (continued) QI9 Cyclohexyl
Me QIOQ19 CJl,
CHt Me QI
O0194-CI-CJaCHt h3
QIO Tsui 9 2-CI-CJ
IiCIIz Me Q
IOQI9 3-Or-CJLCHx
Me QIOQ19 CJs
C(0) Me Q
IOQ19 4-CI-CJ4C(0)
Me QIOQ19 2-C
I-C6114G(0) Me
QIOQ19 3,5-dicl-CJsC
(0) Me QIOQ19
Cyclopropyl-CHz M
e QIOQ19 Cyclo
butyl-C1lz Me
QIOQ19 Cyclopentyl-C
Hg Me QIOQ19
Cyclohexyl-CHz Me
QIOQ19 HC(0
) Me QIOQ
19 MeC(0) Me
QIOQ19 PrC(0
) Me QIOQ1
9 PrC(0)Me
Q10 Table 1 (continued) QI9 BuC(0) Me
QIOQ19 1-Bu(:
(0) Me QIO
0195ec-BuC(0)Me
QIOQ19 t-Buc(0
) Me QIOQ1
9 PenC(0) Me
QIOQ19 11exc(0)
h QIOQ19
MeSOz Me
QIOQ19 EtSOz
Me QIQQ19
Pr5Oz? Ie
QIOQ19 il-Pr5OMe
QIOQ19 4-Me-C, 1I4S
Oz Me QIOQ19
4-CI-CJ(asOtMe
QIOQ19 MeNHSOz
Me QIOQ19
(Me) xNsOz Me
QIOQ19 Ph (Me
) NSOg Me 01
0 mouth 19 MeNlIC(0)
Me
QIOQ19 (Me) JC(0)
M43 Q10 Table 1
(continued) QI R6R702 Q19 Ph(Me)NC(0)
Me QIOQ19 Me
OC (Me)
QIOQ19 EtOC(0)
Me QIOQ19
Pr0C(0)
Me Ro10Q19
II Et
QIOQ19 HPr
QIO019H1-Pr QIOQ
19 HBu 010 mouth 19
Hi-Bu Q 10Q
19 H5ec-Bu QI
OQ19 Ht-Bu QI
OQ19 HPen
QIOQ19 HHex
QIOQ19 II
1110Q19 HE
tOQIO Q19 II PrOQ
IOQ19 H1-PrOQIO Q19 II BuOQ
IO Table 1 (continued) QI R6R7ro 2Q19
tl 1-BuOQIO(
119II 5ec-BuO[110
Q19 Ht-BuOQIOQ19
II Pen0
QIOQ19 It
HexOQIOQ19)I
CIIzCH=CI
Lz Ro10Q19 I
I CIIZCECII
QIOQ19 11 C
l1zCN QIO+1119
HC120CII3 QIOQ19
11
CH20C112CII:I
10Q19 tl C
l1zOCHzCI(zcHx QIOQ19
HCl1zC)lzOcTo Q
IOQ19 II C
l1zCIlzOCHzCIIa QIOQ19
tl C1hOCH
(CHz) z QIOQ19 H
CIIzSCHs QIOQ19
HCHzSClhCHz QIOΩ19
It Cl1zS(
JIzC)lzcHa QIOQ19
II CHzCIIzSCl1
311!10 Table l (continued) Mouth I R6R702Q19
HCH2Cl1zSCHzCI(s
B10Ω19 II
CHzSCH(CIKO)z
QIOQ19 II
Cyclopropyl 010 mouth 19
1st eye
Cyclobutyl 010 units
19 HCyclopentyl
QIOQ19 I
I Cycloh
exyl b10Ω19
II Ca1l, CI+,
QIOQ19 H4-CI-C
JLClh QIOQ19 H2-
CI-C, 1LCH! QIOQ19
H3-Br-CJlaClh QIOQ1
9 HCJsC(0) QIO
Q19 II 4-C
I-C6H4C(0) QIOQ19
tl 2-CI-CJ4C(0
) 010 mouth 19 H3,5-
dicl-C,11,C(0) QIOQ19
HCyclopropVl-CIlz 0
10Q19 HCyclobutyl-CL
QIOΩ19 HCyclopen
tyl-CHz QIOQ19 II
Cyclohexyl-C1lz
QIO Table 1 (continued) QI R6R7Q2 Q19 HIIc(0) QIO
Q19 tl M
eC(0) QIOQ19 II
Etc(0)
QIOQ19)l
PrC(0) QIOQ19
II 1-PrC(0)
QIOQ19 It
BuC(0) QIOQ19
If 1-BuC(
0) QIOQ19 It
5ec-BuC(0) Q
IOQ19 Ht-BuC(0)
QIOQ19 II
PenC (0) QIOQ19
tl HexC(0)
QIOQ19 HMeSOz
QIOQ19 HEtSOt
QIOQ19 II
Pr5Oz QIOQ19
It
1-Pr5Oz QIOQ
19 H4-Me-C6HnSOz
QIOQI9 11 4-
CI-C6H4SO2010 mouth 19
It Me
NH5Ot QIO Table 1 (lX
QI R6R7Q2 Q19 H(Me)zNsOz QIOQ
19 It Ph (Me)NSO
t QIOQ19 HMeNIIC(0)
010 mouth 19 H(Me)J
C(0) QIOQ19 II
PhNHC(0) QIOQ19
HPh(Me)NG(0) QIOQ19
It MeOC(0) Q
IOQ19 II EtOC(0
) QIOQ19 If P
r0C(0) QIOQ19 MeC(0)
Me QllQ19 Et
c(0) Me Q12Q19
PrC(0)? Se Q13
Q19 1-PrC(0) Me
Q14019 MeC(0)
Me
Q15Q19 EtC(0)
Me Q16019
PrC(0)Me
B17019
1-PrC(0) M
e Q18Q19
MeC (0) Me Q19th
1 Table (continued) QI R6R7Q2 Q19 EtC(0) Me
020 mouth 19
PrC(0)Me
Q21Q19 1-
PrC(0)Me
Q22Q19 MeC(0)
Me Q23QI9 E
tc(0) Me Q
24Q19 PrC(0)
Me Q25Q19 1-Pr
C(0) Me Q2
6Q19 MeC(0) M
e Q27Q19 EtC
(0) Me Q2B
Q19 PrC(0) Me
Q29Q19 1-PrC(
0) Me Q30Q
19 MeC(0) Me
Q31019 E
tC(0) Me
Q32Q19 Pr
C(0) Me Q3
3Q19 1-PrC(0) M
e Q34Q19 MeC
(0) Me Q35
Q19 EtC(0) Me
Q36 Table 1 (continued) QI9 1-PrC(0) Me
Q3BQ19 MeC(
0) Me Q42Q
19 EtC(0)
Me
B43Q19 PrC(0)
Me Q44019
1-PrC(0)
Me Q45Q19
MeC(0) Me
Q46Q19 EtC(0)
Me 047Q19
PrC(0)Me
Q48Q19 1-PrC(0)
Me Q49Q19
MeC(0) Me
Q50Q19 EtC(0)
Me Q51Q19
PrC(0)Me
Q52Q19 1-PrC(0
) Me
b53Q19 Me
C(0) Me Q5
4Q19 EtC(0) M
e Q55Q19 PrC
(0) Me Q56
Q19 1-PrC(0) Me
057Q19 MeC(
0) Me QS8th
1 Table (continued) QI R6R7Q2 Q19 EtC(0) Me
Q59QI9 PrC(
0) Me Q60Q
19 1-PrC(0) Me
Q61Q19 MeC(0
) Me Q62Q1
9 Etc(0) Me
Q63Q19 PrC(0)
Me Q64Q19
PrC(0) Me
Q65Q19 MeC(0
) Me Q66Q1
9 EtC(0)Me
Q67Q19 PrC(0)
Me Q68Q19
1-PrC(0) Me
Q69QI9 MeC(0)
Me Q70Q19
Etc(0) Me
Q71Q19 PrC(0)
Me Q72019
1-PrC(0)
Me Q73Q
19 MeC(0)Me
Q74Q19 Etc(0
) Me Q75th
1 Table (continued) QI R6R7Q2 Q19 1-PrC(0) Me
Q77Q19 11ec(
0) Me Q78Q
19 Etc(0) Me
Q79Q19 PrC(0
) Me Q80Q1
9 1-PrC(0) MeQ8
1019 MeC(0)
Me
Q82Q19 Etc(0)
Me Q83Q19
Etc(0) Etc
QIOQ19 EtC(0)
Pr
Ro10Q19 1! tc(0)
1-Pr QIOQ19
Etc(0) Bu
QIOΩ19 EtC(0)
1-Bu QIOQ19
EtC(0) 5ec-Ru
QIOQ19 1EtC(0)
t-Bu QIOQ19
EtC(0) Pen
QIOQ19 Etc(0)
Hex QIOQ19
Etc(0) MeOQIO
Q19 Etc(0) Et
O (110 Table 1 (continued) QI R6R7Q2 Q19 EtC(0) Pr
o QIOQ19 Etc(
0) 1-PrOQIOQ19
EtC(0) BuOQIOQ19
EtC(0) 1-BuOQI
OQ19 EtC(0)
5ec-BuOro10Q19
EtC(0) t-BuOQIOQ19
Etc(0) Pen0
QIOQ19 EtC
(0) 1Iexo
Roe 0Q19 EtC
(0) C112CIl=CI+□
010Q19 EtC(0)
CIl□C1clI QIOQ19
Etc(0) CIIzCN
QIOQ19 EtC(0)
CII□0CIlz QI
OΩ19 EtC(0) CI
I□0CI12C1130IOQ19 Et
C(0) Cl1zOCHzCII□Cl
13 QIOΩ19 Etc(0)
CthC) IzOCtl, 1010 mouths 19
Etc(0)
CIIzCII! 0CII□CH3QIOQ1
9 EtC(0) CH20C
Il(CIl:l)2 QIOQ19
EtC(0) CHzScH3QIO
Table 1 (continued) QI R6R7Q2 Q19 EtC(0) Chz
SCIItC1l+ QIOQ19
EtC(0) CHzSCHzCIl□
Cll3 QIOQ19 Etc(0
)C3lCH2SC)! , Q
IOQ19 Etc(0) C
H2CH25CHIC13 QIOQ19
Etc(0) CIIzSCH(
CH:+)z QIOQ19 Etc
(0) Cyclopropyl
QIOQ19 Etc(0)
Cyclobutyl QIOQ19
EtC(0) Cyclopent
yl QIOQ19 Etc(0)
Cyclohexyl 0
10 units 19 EtC(0)
C6H5Cl+□
010Q19 EtC(0)
4-CI-C6H5Cl+□ 010Q19
EtC(0)
2-CI-C,H,CH2ro10Q19
EtC(0) 3-Br-C611
4CIIz QIO019EtC(0)
C611,C(0)
B10Q19 EtC(0)
4-CI-C,11,C(0) 010
Mouth 19 EtC (0)
2-CI-C6H4G(0)
QIOQ19 EtC(0)
3.5-dtcl-C6H:tC(0)QIO
Q19 Etc(0) Cyc
lopropyl-CHz Q10 Table 1 (continued)
) Q I R6R7Q2 Q19 EtC(0) Cy
clobutyl-C1lz [110019E
tc(0) Cyclopentyl-C
Hz QIOQ19 EtC(0)
Cyclohexyl-C)lx QI
OQ19 EtC(0)
1c(0) QIOQ19 Et
C(0) MeC(0) 0
10 units 19 EtC(0)
EtC(0)
QIOQL9 Etc(0)
PrC(0) QIOQ19
EtC(0) 1-PrC(0
) QIOQ19 EtC(0)
BuC(0) QIOQ
19 Etc(0) 1-
BuC(0) QIOQ19 E
tc(0) 5ec-BuC(0)
QIOQ19 Etc(0)
t-BuC(0) QIOQ1
9 EtC(0) Pen
C(0) QIOQ19 Etc
(0) IIexC(0)
QIOQ19 [4tC(0)
MeSOz 010 mouth 19
EtC(0)
EtSO□ 010Q19
EtC(0) Pr5(h
QIOQ19 1EtC(0)
1-Pr5Oz Q10th
1 Table (continued) QI R6R7Q2 Q19 EtC(0) 4-
Me-Call*SOz 010 mouth 19
Etc(0)
4-CI-CJ, SO□ fullOQ1
9 EtC(0) MeNH
SOz QIOQ19 EtC(
0) (Me) 2NSO2QIOQ1
9 EtC(0)
Ph(Me)NSOz 0
10 units 19 Etc(0)
MeNIIC(0)
QIOQ19 EtC(0
) (Me)JC(0)
B10Q19 Etc(
0) PhNIIC(0) Q
IOQ19 Etc(0)
Ph(Me)NC(0) QIOQ19
EtC(0) MeOC(0)
QIOQ19 Etc(0)
EtOC(0) QIOQ19
Etc(0) Pr0C(
0) QIOQll HM
e Ro10Qll
HMe Q13Qll
HMe Q14011
HMe Q31
Qll II Me
Q35Qll HMe
Q38 Table 1 (continued) QI R6R7Q2 011 It
Me
b60Qll fl
Me Q61011
HMe
Q70Qll It M
e Q72Qll II
Me Q76Qll
HMe Q80Qll
HMe
081 mouth 11 HMe
Q82Qll EtC
(0) Me 01
0 units 11 Etc(0)
Me
Q13Qll EtC(0)
Me Q14Qll Etc
(0) Me Q1
5Qll EtC(0) Me
Q29Qll EtC(0)
? Se Q31Ω
11 Etc(0) Me
Q35Qll Etc(0)
Me Q38Qll
EtC(0) Me
Q60 Table 1 (continued) Qll Etc(0) Me
Q70Qll EtC(0)
Me Q72Ql
l Etc(0) Me
Q76Qll Etc(0)
Me Q80Qll
EtC(0)Me
081g11 Etc(0)
-QB2Qll HEt
010 mouth 11 II
Pr
QIOQll II
1-Pr QIOQl
l HMeSOz QIOQl
l HMeNHSOz QIOQ
ll II C1l□C
H,CIl! QIOQll II
CII□C=CHQIOQll
Etc(0) Etc
QIOQll EtC(0)
Pr QIOQll
EtC(0) 1-Pr
QIOQll Etc(0)
MeSOx
B10 Table 1 (continued) QI R6R7Q2 Qll ctC(0) cll□
CH=C)l! QIOQll E
tc(0) C11,CmiCHQI
OQ12 HMe QIOQ
12 II Me
Q13Q12 HMe
Q14Q12 HMe
Q15Q12 If M
e Q29Q12 HMe
Q31Q12 II
Me Q35Q12
HMe Q38Q12
HMe Q60012■
Hase Q61Q12
II Shame Q70
Q12 II Me
Q72Q12 II
Me Q76Q12
HMe Q80Q12H
Me Q81012
HMe Q82 1st
Table (continued) QI R6R7Q2 Q12 EtC(0) Me
QIOQ12 titc(0)
Me Q1301
2 EtC(0)
Me
Q14Q12 titc(0)
Me Q15Q12 EtC
(0) Me Q2
9Q12 1EtC(0) Me
Q31Q12 Etc(0)
? Se Q35Q
12 Etc(0) Me
Q38Q12 Etc(0)
Me Q60Q12
EtC(0)Me
Q61Q12 EtC(0)
Translation Q70Q12 E
tc(0) Me
Q72Q12 EtC(0)
Me
Roaro Q12 Etc(
Translation of Q8
0Q12 EtC(0) Me
(181Q12 Etc(0
) Me Q82Q
12 II Et
QIOQ12 II
Pr QIO Table 1 (
Continued) QI R6R7ro 2Q12
II 1-Pr
010 mouth 12 HMeSOz
QIOQ12
II MeNIISOz
QIOQ12 +1
C112CII=CIlZ QIOQ12
It
CII□C=a+
B10Q12 EtC(0)
lEt QIOQ12 Etc
(0) Pr 01
0 units 12 EtC(0)
1-Pr
QIOQ12 Etc(0)
MeSOz
B10Q12 EtC(0)
MeNIISOz 01
0 units 12 Etc(0)
clI□CII=CIIZ
QIOQ12 EtC(0)
cll□C:CII QIOQ1
4 HMe QIOQ14
II Vessel
11113Q14 It
Me Ω14Q14 I
I Me Ω1
5Q14 HMe Ω29Q
14 II Me
Q31 Table 1 (continued) QI R6R7Q2 Q14 II Me
Q35014H shame Ω3
8 Q14 It Me
Ω60Q14 HMe
Ω61Q14
HMe
Roa 0Q14 II
Me Ω72Q14 I
I Me Ω7
6Q14 11 Me
Ω80Q14 It
Me Ω81Q14
) I Me
Ω82Q14 EtC(0)
Me QIOQ14 Et
c(0) Me Ω
13Q14 Etc(0) M
e Ω14Q14 EtC(0
) Me Ω15Q
14 EtC(0) Me
Ω29Q14 Etc(0)
Me Ω31Q14
EtC(0)Me
Ω35Q14 1Etc(0)
Me Q38 Table 1 (continued)
QI R6R7Q2 Q14 Etc(0) Me
Ω60Q14 Etc(0)
Me Ω61Q14
Etc(0) Me
Ω70Q14 EtC(0)
Me Ω72Q14
EtC(0) Me
Ω76Q14 [tC(0)
Me Ω80Q14 Et
c(0) Me Q
81Q 14 E tc (0)
Me Ω82Q14 I
t Et 01
0 mouth 14 II
Pr
QIOQ14 tl 1
-Pr QIOQ14 t(
MeSOz QIOQ14 I
f MeNIISOz
QIOQ14 +1 C
Il□Cll=Cl1□ QIOQ14
HC1l□C:=Cl1Q10Q14 Et
C(0) Et Q
IOQ14 Etc(0) P
r QIOQ14 Etc(0
) 1-Pr Q10
Table 1 (continued) Mouth I R6R7Q2Ω14
E tc (0) MeSOz
QIOQ14 Etc(0)
MeNHSOzQ
IOQ14 EtC(0)
CH2CH=CH2QIOQ14 EtC(0
) cll□C=Cl1
QIOQ16 II
Me 010 mouth 16
II
Me Ω13Q16
II
Me Ω14Q1
6 HMe Ω15Q16
HMe
b29Q16 tl
Me Ω31Q16
II Me
Ω35Q16 HMe
Ω38Q16 HMe
Ω60Q16 II
Me Ω61
Q16 II Me
Ω70Q16 HMe
Ω72Q16 II
Me Ω76Q16
II Me
Q80 Table 1 (continued) QI R6R7Q2 Q16 HMe
RO81Q16 HMe
(1B2Q16 Etc(
0) Me QI
OQ16 EtC(0)
Me113016 EtC(0)
Me Q14Q16
EtC(0) Me
Q15Q16 Etc(0)
Me Q29Q16
Et(:(0) Me
Q31Q16 Etc(0)
Me 935016
EtC(0)Me
Q3BQ16 Etc(0)
Me Q60Q16
EtC(0) Me
Q61Q16 Etc(0)
Me Q70Q1
6 Etc(0) Me
Q72Q16 EtC(0)
Me Q76Q
16 Etc(0) Me
Q80Q16 Etc(0
) Me Q81
Table l (continued) QI6 if Et
QIOQ16 It
Pr QIOQ16
If 1-Pr
QIOQ16 HMeSOz
QIOQ16 HMeNHSOz
QIOQ16 II
C112CI1. C1, QIO91611C)12
cEcHQIO Q16 Etc(0) Et
QIOQ16 Etc(0)
Pr 010 mouth 16
Etc(0)
1-Pr Q
IOQ16 EtC(0) Me
SOz QIOQ16 EtC(
0) MeNHSOt 0
10 units 16 Etc(0)
C1I□CmiI=CI+,
QIOQ16 Etc(0)
CHzC=CIl Q10Q
21 It Me
QIOQ21 HMe
Q13Q21 HMe
QI4 Table 1 (continued) Q21 HMe Q29Q
21 II Me
Q31021 II
Me Q35Q21
fl Me
Q38Q21 HMe
Q60Q21 HMe
Q61Q21 HMe
Q70G21 HMe
072Q21 II
Me Q76Q21 HM
e Q80Q21 HMe
Q81Q21 II
Me Q82Q2
1 Etc(0) Me
QIOQ21 Etc(0)
Me Q13Q
21 EtC(0) Me
Q14Q21 Etc(0
) Me Q15
Q21 Etc(0) M
e Q29 Table 1 (continued) QI I? 6 R7Q2
Q21 Etc(0) Me
Q35Q21 EtC(0)
Me Q38Q21
EtC(0) Me
Q60Q21 Etc(0)
Me Q61Q21
Etc(0) Me
Q70ro21 EtC(0)
Me
Q72Q21 Etc(0)
Me 076G2
1 Etc(0) Me
Q80Q21 Etc(0)
Me Q81Q21
Etc(0) Me
Q82Q21 HE t
QIOQ21 HPr
QIOQ21 II 1-
Pr QIOQ21 HMe
SOx QIOQ21 HMe
NIISOz QIO (121If
CIIzC1l=CII
z ro10Q21
HC1I□C MiCI 010 mouth 21
EtC(0)
Et
QIO Table 1 (continued) Q I R6R7Q2 Q21 EtC(0) Pr
QIOQ21 Et
c(0) 1-Pr
010 mouth 21
EtC(0)
MeSOzQ
IOQ21 E tC(0)
MeNllSOz QIO
Ω21 EtC(0) C11
2CI=CII□ QIOQ21 Et
C(0) CIzC=CII
QIOQ24 If
Me QIOQ24 H
Me Q13G24 II
Me Q14Q
24 11 Me
Q15Q24 It
l'le Q29Q24
It Me
Q31Q24 If
Me Q35Q24 II
Me Q38
Q24 HMe Q60Q2
4 II Me
Q61Q24 II
Me Q70Q24
If Me
Q72 Table 1 (continued) QI R6R7Q2 024 HMe
Q76G24 It
Me Q80Q24
II
Me
081 mouth 24 HM
e Q82Q24
Ii tC(0) Me
Q 10Q24 Etc(0
) Me Q13
Q24 Etc(0) M
e Q14Q24 Etc(
0) Me Q1
5024 EtC(0)
Me
Q29024 Etc(0)
Me
Q31Q24 Et
C(0)Me
Q35Q24 EtC(0)
Shame Q38Q24 E t
C(0)Me
Q60ro24 EtC(0)
Me
Q61(124E tC(0
) Me Q70
Q24 Etc(0) M
e QT2Q24
EtC(0)
Me Roaro Q2
4 E tC(0) Me
Q80 Table 1 (continued) Mouth 24 EtC (0)
Me
Ro81Q24 EtC(0)
Me Q82Q24 1(E
t QIOΩ24 It
Pr QIOQ24 II
1-Pr QIOQ24 11
MeSOz QIOQ24
If MeNIISOz QIOQ
24 If CIIzC1l=C)l
z QIO024II
CII□CmiCHQIOQ24 EtC(0)
Et QIOQ24 Etc(
0) Pr QIOQ24
EtC(0) 1-Pr QIO
Q24 EtC(0) MeSOz
QIOQ24 EtC(0)
MeNHSO2QIOQ24 EtC(0)
C11zCII=CHz QIOQ24
Etc(0) CII□C
=Cl1 QIOQ26 If
Me QIOQ26 I
f Me QI3 Table 1 (
Continued) QI R6R7Q2 026 HMe Q14Q2
6 HMe
B15G26 1
Me Q29Q26 II
Me Q310
26 It
Me
Q35026 HMe
Q38026
tl
Me Q6
0Q26 II Me
Q61Q26 It
Me Q70G26
) I Me
Q72Q26 II
Me Q76Q26H
Me Q80Q26 II
Me Q81G
26 HMe Q82Q26
EtC(0) Me
010Q26 Etc(0)
Me Q13Q26
EtC(0) Me
Q14Q26 EtC(0)
Me Q15 Table 1 (continued) QI R6R7ro 2Q26
E tC(0) Me
Ω29G26 Etc(0)
Me Ω31G26
E tc (0) Me
Ω35G26 EtC(0)
Me
B38Q26 E
tc (0) Me
Ω60G26 EtC(0)
Me Ω61G26 E
tC(0)Me
Ω70G26 Etc(0)
Me 072G26 E tC
(0) Me Q7
6026 EtC(0)
Me
080 units 26 Etc(0
) Me
Ω81G26
ELC(0)
and 1e
RO82Q26 II
Ct
RO10Q26 HPr
Ω10G26 If
1-Pr 010 mouth 26
I(MeSOg
QIOQ26 II
MeNIISOz QI
OQ26 HCHzCII=CIIz
Q10 Table 1 (continued) Mouth I R6R7Q2Q26
II CII□C=C
l1 QIOQ26 EtC(0
) Et QIOQ
26 Etc(0) Pr
QIOQ26 Etc(0
) 1-Pr
QIOQ26 Et
c(0)MeSOg
B1OQ26
Etc(0) Me
NHSOz Ro10Q26
E tc (0) CI□Cll
=C1h QIOQ26 EtC(
0) CII□C=C1(QIOQ
28 HMe QIOQ28
HMe Ω13G28
HMe Ω14G28
II Shame Ω15
G28 If Me
Q29028 If
Me
Ω31G28 f
l Me Ω35
G28 HMe Q38Ω2
8 HMe Ω60G28
tl Me
Q61 Table 1 (continued) QI R6R702 G28 HMe, 070
Q28 fl Me
Ω72G28 II
Me Ω76G28
II Me
080 mouth 28 l (M
e Ω81G28
11 Me
Ω82G28 EtC(0)
Me QIOQ28
E tc (0) Me
Q13028 EtC(
0) Me
Ω14G28
Etc(0) Me
Ω15G28 E tC(0)
Me Ω29G28
Etc(0) Me
Ω31G28 E tc (0)
Me Q350
28 Etc(0)
Me
Ω38G28 EtC(0
) Me
060 mouths 28
Etc(0)
Me Ω6
1G28 E tC(0)
Me Ω70G28 E
tC(0)Me
Q72 Table 1 (continued) QI R6R7Q2 Q28 Etc(0) Me
Ω76G28 EtC(0)
Me Ω80G28
EtC(0)
Me
RO81Q28 E tc (0)
Me Ω82G28
II Et
QIOQ28 HPr Q
IOQ28 H1-Pr Q
IOQ28 HMeSOz Q
IOQ28 HMeNHSOz
QIOQ2B II
C1l□Cl1=C1h
B10Q28 II
cozc=co QIO0281
ELc(0) Et
QIOQ28 EtC(0)
Pr QIOQ28
EtC(0) 1-Pr
QIOQ28
Etc(0) MeSOz
QIOQ28 1E tC(0)
MeNIISOg QIOQ28
EtC(0) C1l□Cl1=C
1h QIOQ28 EtC(0)
cll□C=CII
QIO Table 1 (continued) g30 II -Ω1
0Q30 If Me
Ω13Q30 HMe
Ω14Q30 HMe
Ω15Q30 It
Me Ω29Q30
HMe Q31 (130H
Me Ω35Q30 II
Isao Ω38Q3
0 II Me
Ω60Q30 II
Me Ω61Q30
It Me
Ω70Q30 It
Me Ω72Q30
II Me
Ω76Q30 HMe Ω
80Q30 1+ Me
Ω81Q30
II
Me Ω82Q3
0 Etc(0)
Me
QIOQ30 1EtC(0)
Me QI3 1st
Table (continued) QI R6R7ro 2030
EtC(0)
Me
Ω14Q30 [1tC(0)
Me
Ω15Q30 EtC(
0) Me Ω29
Q30 BtC(0) Me
Ω31Q30 EL
C(0)M
e b3503
0 EtC(0)
Me
038Q30 1E tC(0)
Me Ω60Q30
EtC(0)
Me
B61Q30 E tC(0)
Me Ω70Q30
E tC(0) Me
Ω72Q30 E tC(0)
Me Ω76Q30
EtC(0)
Me ro
80Q30 EtC(0)Me
Ω81Q30 EtC(0)
Me
082Q30
It IE
t RO10Q30
If
Pr ro1
0Ω30 II i-P
r Q 10Ω30 If
MeSOz QIO
Table 1 (continued) Q30 If
MeNIIS02
B10Q30 HCH2CH=CI+□
[110Q30 II
CIl□c=o+ QIOQ30
Etc(0) Etc
QIOQ30 Etc(0)
Pr QIO(130Etc
(0) 1-Pr
Ω10Q30 EtC(0)
MeSOz
QIOQ30 E t
C(0) MeNllSOz
QIOQ30 Etc(0)
cll□CI+, CI+2
010Q30 Etc(0)
CH□c=oIQIO port 31
HMe
QIOQ31 II
Me Ω13Q31
It
Me ro14Q31
II Gate e
Ω15Q31 It
Me
Ω29Q31
If
Me
B31Q31 If
Me 035Q31
II Me
Q38 Table 1 (continued) Mouth 31 HMe
Ω60Q31 HMe
Ω61Q31 if
Me Ω70Q31
tl Me
072Q31 HMe
Ω76Q31 If
Me
080 mouth 31
fl
Me
Ω81Q31 II
Me
Ω82Q31 EtC
(0) Me QI
O031Etc(0) Me
Ω13Q31 BtC(0)
Me Ω14Q31
Etc(0) Me
Ω15Q31 1Etc(0)
Me Ω29Q31
EtC(0)
Me
Ω31Q31 Etc(0)
Me Q35Q31 1E
tC(0)Me
Ω38Q31 E tc (0)
Me Q60 Table 1 (continued)
QI R6R7Q2 Q31 EtC(0) Me
Ω70Q31 EtC(0)
Me Ω72Q31
EtC(0)Me
Ω76Q31 EtC(0)
Me Ω80Q31
1EtC(0) Me
Ω81Q31 Etc(0)
Me
Ω82Q31 II
Et QIOQ
31 If Pr
QIOQ31 H1-Pr
QIOQ31 II
MeSOz QIOQ31
HMeNllSOz QIOQ31
II
CII□Cl1=CI+□
B10Q31 II Cl
1zC=CHQIOQ31 EtC(0)
Et [110Q31
E tc (0) Pr
010 mouth 31 Etc(
0) 1-Pr
QIOQ31
E tC(0) MeSOz
010 mouth 31 Etc(0)
Gate eNIIsO
z Q10 Table 1 (
Continued) Q31 EtC(0) CIl
, CIl, CIl QIOQ31
EtC(0)Cl
zC=CHl ro10Q33
tl Me
010 mouth 33 HMe
Ω13Q33
It Me
Ω14Q33 Hachi QI5(
133II Me
Ω29Q33 HMe
Ω31Q33 II M
e Ω35Q33 If
Me Ω38Q3
3 If Me
Ω60Q33 HMe
Ω61Q33 HMe
Ω70Q33 it
Me Ω72Q33 HMe
Ω76Q33 II
Me Ω80Q33
It Me
Ω81Q33 II
Me (182 Table 1 (continued)
QI R6R7Q2 Q33 EtC(0) Me
QIOQ33 EtC(0)
Me Ω13Q33
EtC(0) Me
Ω14Q33 Etc(0)
Me Ω15Q33
E tc (0) Me
Ω29Q33 EtC(0)
Me Ω31Q33
Etc(0) Me
Ω35Q33 EtC(0)
Shame Q3BQ33 E tc
(0) Me Ω6
0Q33 Etc(0) Me
Ω61Q33 E tc (
0) Me 070
Q33 E tC(0) Me
Ω72Q33 titc(0
) Me Ω76Q
33 E tc (0) Me
080 33 E
tc(0) M
e Ω81Q33
E tc (0) Me
Ω82Q33 II
Et QIOQ33
It Pr
Q10 Table 1 (continued) QI R6R7Q2 033 If
1-Pr
QIOQ33 HM
eSOz Ro10Q33
HMeNHSOz
B10Q33 II
CIzCII・CIIz 010 units
33 11
ChzCmiCII
QIOQ33 EtC(0)
Et QIOQ33
1Etc(0) Pr
QIOQ33 Etc(0)
1-Pr QIOQ
33 EtC(0)MeS
Oz QIOQ33 EtC
(0) MeNHSOz
QIOQ33E LC(0)
CI□CII=CIIz QIO
Q33 EtC(0) C
)ticmi CIl QIOQ37
1 Me
QIOQ37 HMe Ω
13Q37 II M
e Ω14Q37 II
Me Ω15Q
37 HMe Ω29Q3
7 II Me
Q31 Table 1 (continued) QI R6R702 Q37 II Me
Ω35Q37 I
I Me
Ω38Q37
) l Me
Ω60Q37 If
Me
Ω61Q37
II
Me
Roa 0Q37 H shame Ω7
2Q37 If Me
Ω76Q37 II
Me Ω80Q37
tl Me
Ω81Q37 II
Me Ω82Q37 Et
c(0) Me Q
IO+137 Etc(0)
Me
(113Q37 EtC(0)
Me Ω14Q37
Etc(0) Me
Ω15Q37 EtC(0)
Me Ω29Q37
EtC(0)
Me Ω31
Q37 Etc(0)
Me
B35037 E tc (
0) Me Q38
Table 1 (continued) QI R6R7Q2 Q37 E tc (0) M
e Ω60Q37
Etc(0)
Me Ω61Q37
E tc (0) Me
Ω70Q37 E tc (0)
Me Ω72Q3
7 Etc(0)
Me
Ω76Q37 ELC(0
) Me
Ω80Q37
E tc (0) Me
Ω81Q37 EtC(0)
Me
Ω82Q37 I
I Et QI
OQ37 It
Pr
B10Q37 II 1
-Pr QIOQ37 II
MeSO,QIOQ37
It MeNIISOz
QIOQ37 if
CIIzCII=C1lz QIO
Q37 II CIl□c
=co QIOQ37 E
tc(0) Et
b10Q37
EtC(0) Pr
Q10 Table 1 (continued) Mouth I R6R702G37
EtC(0) MeSOz
QIOQ37 EtC(0)
MeNIISOz QIOΩ3
7 EtC(0) Cll2CI
l=CI12 QIOQ37 EtC
(0) cll□C:l:C1l
QIOQ36 II
Me QIOQ36
II Chest Ω13
Q36 tl
Me
B14Q36 II M
e Ω15Q36 II
Me Ω29Q3
6 II Me
Ω31Q36 11
Me Ω35Q36
It Me Ω
38Q36 It Me
Ω60Q36 II
Me Ω61Q36
It Me
Ω70Q36 II
Me Ω72Q36
HMe
Roaro Q36 If
Me Q80 Table 1 (continued) QI R61?7 Q20
36 II
Me
RO81Q36 It
Me Ω82Q36
Etc(0) Me
QIOQ36 Etc(0)
Me Ω13Q36
EtC(0)
Me ro14Q36
Etc(0)
Me ro15
Q36 E tC(0) Me
Ω29Q36 EtC(0)
Me Ω31Q3
6 Etc(0)
Me
B35Q36 Etc(0)
)'le Ω38Q3
6 E tc (0) Me
Ω60Q36 Et
C(0) M
e Ro61Q3
6 E tc (0) Me
Ω70Q36 Et
C(0)Me
Ω72Q36
E tc (0) Me
Ω76Q36 E tC(0)
Me Ω80Q36
E tc (0) Me
Ω81Q36 E tc (0)
Me Q82 1st
Table (continued) QI R6R7Q2 Q36 HEt QIOQ3
6 HPr QIOQ36
tl 1-Pr
010 mouth 36 HMeS
Oz QIOQ36
If MeNHSOz
QIOQ36 II
CHzCIl=CHz QIOQ3
6 II HzC”CI
l QIOQ36 EtC(0)
Et QIOQ36
EtC(0) Pr
QIOQ36 Etc(0)
1-Pr 010 mouth 36
EtC(0)
MeSOz
QIOQ36 EtC(0)
MeNIISOz 010 mouth 36
EtC(0)
CHzCIl,CIIz
QIOQ36 Etc(0)
CHzCmiCHQIOQ38
II Me
QIOQ38 tl
Me Q13Q38 HMe
Q14Q38 HMe
QI5 Table 1 (continued) QI R6R7Q2 038 It
Me
Q29Q38 II
Me Q31Q38
II Me
Q35Q38 II Shame
Q38Q38 II
Me Q60Q38
HMe Q61Q38
II Me Q7
0Q38 HMe Q72Q
38 II Me
Q76Q38 tl
Me Q80Q38
HMe Q81Q38 II
Me Q820
38 Etc(0)
Me
QIOQ38 ELC(0)
Me Q13Q38
Etc(0) Me
Q14038 Etc(0)
Me
QI5 (138Etc(0)
Me Q29Q38
EtC(0) Me
Q31 Table 1 (continued) QI R6R7Q2 038 EtC(0)
Me
Q35Q38 E tC(0)
Me Q38Q38
EtC(0) MeQ60Q38
Etc(0) Me
Q61038 EtC(0)
Me
Q70Q38
EtC(0) Me
Q72038 Etc(0)
Me
Q76Q38 E t
C(0) Me 0
80 units 38 EtC(0)
Me
Q81Q38 E tC(0
) Me Q82Q
38 HEt QIOQ38
HPr QIOQ3B
II 1-Pr
QIOQ38 II
MeSOz QIOQ38
II MeNHSOz
010 mouth 38 II
CH2Cl, C1, Q
IOQ38 II CII
zCaCII QIO038EtC(0)
Et
Q10 Table 1 (continued)
) QI R6R7Q2 Q38 Etc(0) Pr
QIOQ38 Etc(0)
1-Pr QIOQ
38 EmuC(0) MeSOz
010 mouth 38 [E
tC(0)MeN
lISOZ QIOQ3
8 Etc(0) Cl1iCH
=CIl□ QIOQ38 Etc(0
) CH□C=CHQIOQIOHMe
QIOQIOEtc(0)
Me QIOQ13
II Me
QIOQ13 Etc(0)
Me QIOQ15 II
Me QIO
Q15 ctC(0)
Me ro1
0Q17 It Me
QIOQ17 FitC(0)
Me QIOQI
OHMe QIOQIOEtC(0)
Me QIOQ2
0 If Me
QiOQ20 EtC(0)
Me QIO Table 1 (
Continued) Mouth I R6R7Q2Q22
HMe QIOQ22 Et
c(0) Me Q
IOQ23 It Me
QIOQ23 Etc(0)
Me QIOQ2
5 II Me
QIOQ25 EtC(0)
Me QIOQ27
HMe QIOQ27 E
tc(0) Me
QIOQ29 It M
e QIOQ29 E tC(
0) Me QIO
Q30 II Me
QIOQ30 Etc(0)
Me QIOQ32
HMe QIOQ32
Etc(0) Me
QIOQ34 HMe
Ro10Q34 Et
c(0) Me Q
IOQ35 It Me
QIOΩ35 EtC(0)
Me QIO No.
1 Table (continued) QI R6R7Q2 039 If
Me
QIOQ39 Et
c(0) Me
010Q40 HM
e Ω10Q40 E tC(
0) Me Q 1
0 mouth 41 If
Me
Ω10041 Etc(0
) Me QIOQ
42 11 Me
QIOQ42 CtC(0)
Me QIOQ43
It Me
QIOQ43 EtC(0)
Me QIOQ44 HM
e 010 mouth 44 E
tC(0) Me
QIOQ45
If Me
010 units 45 Etc(0)
Me
Ω10Q46 It
Me 010
Mouth 46 EtC (0)
Me
010guchi47' It
Me
QIOQ47
Etc(0) Corner
QIO Table 1 (continued) Mouth I R61?7
Q2Ω48 If
Me QIOQ48
Etc(0) Shame
QIOQ49 HMe
QIOQ49 Etc(0)
Me QIOQ50
If Me
QIOQ50 EtC(0)
Me 010Q51
It Me
QIOQ51 EtC(0)
Me QIOQ52
II Me
QIOQ52 E tC(0)
Me QIOQ53
If Me
QIOQ53 Etc(0)
Me QIOQ54
If Me
QIO054 inhibit C(0) Me
QIOQ55 It
Me QIOΩ55
Etc(0) Gate e
QIOQ56 II
Me QIOQ56
Etc(0) Me
QIO Table 1 (continued) Mouth I R6R7Q2Q57
HMe QIOQ57
EtC(0)Me
QIOQ58 II
Me QIOQ58 E
tc (0) Me
Q 10Q59 If
Me QIOQ59
Etc(0) Me
QIOQ60 If
Me
B10Q60 E tC(0)
Me QIOQ6
1 II Me
QIOQ61 HtC(0)
Me Q 10Q6
2 II Me
(110Q62 E tc (0
) Me Q 1
0Q63 II Me
QIOQ63 [1tC(
0) Me QI
O(164It Me
QIOQ64 1Etc(0)
Me QIOQ65
II
Me Ro10Q6
5 EtC(0) Me
QIO Table 1 (continued) QI R6R7Q2 Q66 HMe 010 mouth 6
6 EtC(0)
Me
QIOQ67 HMe
010 mouth 67
EtC(0)
Me
QIOQ68 HMe QI
O068Etc(0) Me
QIOQ69 HMe
QIOQ69 EtC(0)
Me QIOQ70
If Me Q
IO lower 0 EtC(0)
Me
QIOQ71 II
Me QIOQ71
EtC(0) Me
QIOQ72 It
Me QIOQ72
Etc(0) Me
QIOQ73 HMe
QIOQ73 Etc(0)
1Ile QIOQ74 I
I Me QI
OQ74 Etc(0)
Me
B10 Table 1 (continued) Mouth I R6R7Q2075
II
Me
B10Q75 Etc(0)
Me
B10G76 II
Me (110Q76
EtC(0)Me
QIOQ77 HMe
QIOQ77 Etc(0)
Me QIO Roa 8
It Me
B10078 Etc.
(0) Me QI
OQ79 It' Me
QIO Roa 9 Et
c(0) Me
QIOQ80
) I Me
010 units 80 EtC(0)
Me
QIOQ81
If M
e Ro10Q81
EtC(0)
Me Ro10Q8
2 If Me
QIOQ82 Etc(0)
Me QIOQ83
II Me
QIOQ83 EtC(0)
Me Q10 Table 1 (continued) Ω84 If Me
QIOQ84 HMe
Ω13G84 tl
Me Ω14G84
HMe Q15Ω84
tl
Me ro
29Ω84 If Me
Ω31G84 II
Me Ω35G84
it me
Ω38G84 11
Me Q60ro84
HMe
Ω61G84 II
Me
Roa 0Q84 II
Me Ω72G
84 It Me
Ω76G84 fl
Me Ω80G84
II Me
Ω81G84 II
Me Ω82G84 EtC (
0) Me 010
Q84 EtC(0) Me
Ω13 Table 1 (continued) Ω84 EtC (0)
Me
Q14084 E
tC(0) M
e b15Q84
EtC(0)
Me
B29G84 EtC(0)
Me Ω31G84 E tc
(0) Me Ω
35G84 EtC(0)
Me Q3BQ84 E tC
(0) Me Ω6
0G84 EtC(0) Me
Ω61G84 E
tC(0)
Me Roa 0Q8
4 Etc(0) Me
Q72084 Etc(
0) Me
Ω76G84
E tc (0) Hashi
080Q84 Etc(0)
Me Ω81G84 E
tc (0) Me
Ω82G84 II E
t QIOQ84 HPr
QIOQ84 II
1-Pr QIOQ84
II MeSOz
QIO Table 1 (continued) QI R6R7Q2 Q84 HMeNIISOz
QIO084+1 Cl1C=C
1lz QIOQ84 +1
Cl1zC=CHQIO084Etc(
0) Et
QIOQ84 EtC
(0) Pr QI
OQ84 EtC(0)
1-Pr
QIOQ84 EtC(0)
MeSOz QIO (184E t
c (0) MeNllSOz
QIOQ84 EtC(0)
CH2CII=CII□ QIOQ84
EtC(0) CIIZC
MiCHQIOQ85 II
Me QIOQ85H
Me Q13Q85 II
Me Q100
85 II Me
Q10085 It
Me Q29Q85
HMe Q31Q85
II Me Q
35085 II Me
Q38 Table 1 (continued) QI R6R7Q2 Q85 II
Me
060 mouth 85 II
Me
Q1085 1
1? SeQ
70Q85 II
Me
Lower 2G85 II
Me Q76Q8
5 If Me
Q10085 It
Me Q1085
11
Me
Ro82Q85 Etc(0)
Me QIOQ85
Etc(0)
Me Q13Q85
E tc (0) Me
Ω14085 Et
C(0)Me
Q10085
E tC(0) Me
Q29085 EtC(
0) Me
Q31Q85
Etc(0)
Me 0
35Q85 E tC(0)
Me Q38085
Etc(0)
Me Q60
Ro85 EtC(0)
Me
RO61 Table 1 (continued) QI R6R7Q2 Q85 EtC(0) Me
Q70Q85 E LC(0)
Me Q72Ω8
5 Etc(0) Me
Q76Q85 EtC(
0) Me
b80Q85
E tC(0) Me
Q81085 EtC(0)
Me
Q82Q85
II
Et Ro10Q85
If Pr
QIOQ85 It
1-Pr QIOQ85
It MeSOz
QIOQ85 II M
eNHSOz QIOQ85
II CH2
Cll=Cl1□ 010 mouth 85
11
CIl□CmiC1l
QIOQ85 EtC(0)
Et QIOQ85 E
tC(0) Pr
QIOQ85 Etc(0)
1-Pr QIOQ85 Et
C(0)MeSOz
QIOQ85 [1tC(0)
MeNIISOz QIO Table 1 (continued)
QI R6R7Q2 Q85 Etc(0)
CIl□Cl1=CII□
Q10085 Etc(0)
CHzCmiCHQIOQ86
II
Me 010 mouth 86
)l
Me
Q10085 HMe
Q14086 II
Me
Q15086
It
MeQ
29Q86 II
Me
B31G86 HMe
Q35Q86 If
Me Q3BQ86
HMe Q10085
HMe Q1085
HMe Q10085
II
Me ro
A2Q86 It Me
Q76Q86 HMe
Q10085 It
Me Q1085
HMe Q82 Table 1 (continued)
) QI R6R7ro2Q86
Etc(0) Me
010 units 86 Etc(0)
Me
Q13Q86 EtC
(0) Me Q1
4Q86 Etc(0) Me
Q15Q86 E tc (
0) Me Q29
Q86 Etc(0) Me
Q31Q86 Etc(0)
Me Q35 (18
6EtC(0)Me
Q3BG86 Etc(0)
Me
RO60Q86 E
tc(0) Me
Q61G86 E tc (0)
Me Q70Q86 E
tC(0) Me
Q72086 E tc (0)
Me Q76Q86 Et
C(0) Me Q
80Q86 Etc(0) M
e Q81Q86 Etc(0
) Me Q82G
86 tl Et
010 mouth 86 HP
r Q10 1st
Table (continued) QI R6R7Q2 Q86 If 1-Pr
010 mouth 86H
MeSOt QIO
Q86 II MeNH
SOg 010 mouth 86
II CH
zCH=CHg QIOQ8
6 HC1hC=CHQIOQ86 E
tc(0) Et
010 units 86 Etc(0)
Pr
QIOQ86 Etc(0)
1-Pr QIOQ
86 Etc(0) MeSOz
QIOQ86 EtC(0)
Translated by NHSO□ QIOQ86
EtC(0) CHgCH=C
IIz QIOQ86 HtC(0)
C1hC=CH010 port 87
HMe
QIOQ87 II
FSeQ13Q87 If
Me Q14Q87H
Me Q150B7
II
Me Q2
9Q87 II NeQ3
1 Table 1 (continued) Mouth R6R7Q2Q87
HMe Q35Q87 I
f Me Q3
8Q87 II Me
Q60Q87
if
Me Ro61Q
87 II Me
Q70ro87 HM
e Q72QB
7 If Me
Q76G87 II
Me Q80Q87
HMe Q81Q87 I
f Me Q8
2Q87 EtC(0) Me
QIOQ87 EtC(0)
Me Q13Q
87 EtC(0) Me
Q14087 CtC(
0) Me
Q15Q87 E
tC(0)Me
Q29087 Etc(0)
Me
Q31QB7 E tc
(0) Me Q
35087 EtC(0)
Me
038 Table 1 (continued) QI R6R7Q2 Q8'7EtC(0) Translation
Q60QB7 EtC(0)
Shame Q61Q87 EtC
(0) Me Q7
0QB7 EtC(0) Me
Q720B7 Etc(0)
Me Q76QB
7 EtC(0) Me
Q80Q87 Etc(0)
Me Q81Q87
Etc(0)? Se
Q82a81 HEt
QIOQ87 HPr
QIOQ87 H1-Pr
QIOQ87 HMeSOz
QIOQ87 HMeNllSOz
QIOQ87 HC1hC=CHz
QIOQB7 II
CHzC:i:CI 010 mouth 87
EtC(0)
Et
010 units 87 Etc(0)
Pr
QIOQ87 EtC(0
) 1-Pr QIO
Table 1 (continued) QI R6R7Q2 Q87 Etc(0) MeSO,QI
OQ87 Etc(0) MeNHSO
z QIOQ87 EtC(0)
C11, Cl1=CIl□ QIOQ87
EtC(0) CIl□C41iCII
QIOQ88 HMe QI
OQ88 It Me
Ω13G88 If Me
Ω14G88 It Me
Ω15G88 HMe Ω2
9G88 If Me
Ω31G88 II Me
Ω35G88 HMe Ω38G
88 HMe
RO60Q88 HMe
Ω61088″ HMe Ω70G
88 II Me Ω7
2G88 tl Me
Ω76G88 HMe
B80 Table 1 (continued) Q88 II Me
Ω81088 I
I Me
Ω82088
Etc(0)
Me
QIOQ88 Etc(0)
Me Ω13G88 EtC(0
) Me Ω14G
88 1Etc(0) Me
Ω15G88 E tC(0)
Me Ω29G88
EtC(0) Arm Ω
31G88 Etc (0)
Me Ω35G88 Etc (
0) Me Ω38G8
8 E tC(0) Me
Ω60G88 [:tC(0)
Shame Ω61G88
E tC(0) Me
Ω70G88 E tc (0)
Me Ω72G88
E tC(0) Me
Ω76G88 E tC(0)
Me Ω80G88
1E tC(0) Me
Q81 Table 1 (continued) QI R6R7Q2 Q88 HEt QIOQ
88 It Pr
QIOQ88 H1-Pr
QIOQ88! I
MeSOz QIOQ8
8 It MeNllS
Oz QIOQ88 II
CI□CI+. CII□
QIO08B II
CII□C<II QIOQ88
EtC(0) Et
QIOQ88 1EtC(0)
Pr
Ro10Q88 Etc(0)
1-Pr QIOQ88
E tC(0) MeSO
z 010Q88 EtC(0
) MeNllSOz
QIOQ88 EtC(0)
CIl□CH=CIl□ QIOQ88
Etc(0) CII□C=
C11 [110G89 It
Me QIOQ89
II Me
Ω13G89 It
Me Ω14G89 I
t Me QI
5 Table 1 (continued) QI R6R7Q2 Q89 HMe Ω29G8
9 It Me
Ω31G89 II
Me Ω35G89 H
Me Ω38G89 II
Me Ω60G
89 HMe Ω61G89
HMe Ω70G89
It Me
Ω72G89 II M
e Ω76G89 tl
Me Ω80G89
II Me
Ω81G89 II Me
Ω82G89 E tc (
0) Me Ω10
G89 Etc(0) Me
Ω13G89 E tC(0)
Gate e Ω14G8
9 Etc(0) Me
Ω15G89 E LC(0)
Me Ω29G89
EtC(0) Gate e
Q31 Table 1 (continued) Q89 E tC(0)
Me Q35Q89 Etc.
(0) Me Q
38Q89 EtC(0)
He Q60Q89 Et
C(0) Me
Q61G89 E tC(0)
Me Q70Q89
Etc(0) Me
Q72Q89 E tc (0)
Me 076089
E tC(0) Me
Q80089 E tC(0)
Me Q81Q8
9 E tc (0) M
e Q82Q89 HHt
QIOΩ89 II
Pr QIOQ8
9 If 1-Pr
QIOQ89 II
MeSOz QIOQ8
9 tl MeNIIS
Oz 010 mouth 89
II C
112CII=CII2 01
0Q89 HCH2CmiC1I
QIOQ89 EtC(0)
Et QIO Table 1 (continued)
Q89 EtC(0) Pr
QIOQ89 EtC(0)
1-Pr QIOQ
89 Etc(0) MeSOz
QIOQ89 EtC(0)
MeNHSOi QIOQ
89 EtC(0) CI(zc
H=cII□ QIOQ89 Etc(
0) HzC-'CIl
QIOQ90 HMe QI
OQ90 Etc(0) M
e QIO (hereinafter referred to as margin) Table 2 Qll II Me QIOQll
Etc(0) Me QIOQ12
HMe QLO Q12 Etc(0) Me QIO
Q14 It Me 010guchi14
Etc(0)
Me 0
10 mouths 16 HMe
QIOQ16 EtC(0)
Me QIOQ19 HMe
QIO Q19 Etc(0) Me Q10
Q21 It Me QIOQ21
Etc(0) Me [110th
2 Table (continued) Q24 Etc(0) M
e 010 mouth 26
II
Me QIOQ26
EtC(0)Me
QIOQ28 If
Me QIOQ2B
E tC(0) Me
QIOQ30 HMe
QIOQ30 EtC(0)
Me QIOQ31
II Me
QIOQ31 Etc(0)
Me QIOQ33
II Shame QI
OQ33 EtC(0)
Me QIOQ36 If
Me QIO
Q36 Etc(0) M
e QIOQ31 If
Me QIOQ
37 EtC(0)Me
910 units 38
HMe QIO 3rd
Table 9゜mouth 19 II
2019 Me
2Q19
Et 2 019 Pr 2 QI9 1-Pr 2 019 C1I□Cl1=C11□
2019 C1I□C=co
2Q19 C1l□CN 2 Q19 CH20CH:l 2Q19 C
1I□0C112CI+3 2Q19 CHzO
CH (CHi)! 2Q19 Cyclopro
pyl 2 Table 3 (continued) QI9 Cyclobutyl
2Q19 Cyclopentyl
2019 Cyclohexyl
2Q19 C, 11, C
Il□ 2Q19 CJSC(0
) 2Q19 Cyclopr
opyl-CHz 2Q19 Cycl
obutyl-Ctlz 2Q19
Cyclopentyl-Ctlz 2Q19
Cyclohexyl-Ctlz
2Q19 11c(0) 2Q
19 MeC(0) 2Q1
9 EtC(0) 2Q19
PrC(0) 2Q19
1-PrC(0) 2Q19
BuC (0) 2Q19
1-BuC(0) 2919 5
ec-BuC(0) 2Q19
L-Buc (0) 2 Table 3 (continued) QI9 PenC (0) 2Q19
HexC(0) 2Q19 MeS
Oz 2Q19 EtSO□
2Q19 Pr5Oz 2Q19
1-Pr5Oz 2Q19 Me
NllSOz 2Q19 (Me
)zNsOz 2Q19 MeN)Ic(
0) 2Q19 (Me)zNc(0)
2Q19 MeOC(0) 2
019 EtoC (0) 2Q19
Pr0C(0) 2Q19 II
3 Q19 Me 3 Q19 Et 3 Q19 Pr 3 Table 3 (continued) QI R6n Q19 CH2CH=CHz
3Q19 HzC=cu 3Q
19 CIIzCN 3Q1
9 C1I□0C11,3 Q19 CHzOC1I□C1l:l
3019 C1I□0C11 (CHi 3
”) 2 3019 Cycl
opropyl 3Q19
Cyclobutyl 3Q19
Cyclopentyl 3Q1
9 Cyclohexyl 3Q
19 C,ll5cII□ 3Q
19 C611SC(0) 3
Q19 Cyclopropyl-C1lz
3Q19 Cyclobutyl-C1l
z 3Q19 Cyclopenty
l-CHz 3Q19 Cyclohe
xyl-C1lz 3Q19 11
c(0) 3Table 3 (continued) QI R6n Q19 EtC(0) 3Q
19 PrC(0) 301
9 1-PrC(0)
3Q19 BuC(0)
3Q19 1-BuC(0)
3019 5ec-BuC(0)
3Q19 t-Buc(0)
3Q19 PenC(0)
3019 11exC(0)
3Q19 Me
SOz 3019
Etsoz 3Q
19 Pr5Oz 3Q19
1-Pr5Oz 3Q19
MeNIISOz 3Q19
(Me) zNsO* 3Q1
9 MeNIIC(0) 3Q
19 (Me)JC(0) 30
19 MeOC(0)
3Table 3 (continued) QI R6n Q19 EtOC(0) 3Q
19 Pr0C(0) 3Q1
9 H4 019Me 4
Q19 Et 4Q19
Pr 4019
1-Pr 4
Q19 cnzco, cuz 4
Q19 CHIC MiC)I
4Q19 CIIZCN
4Q19 CH□OCI+3 4
Q19 CToOCH1CI+3
4Q19 C11zOCII(CHa)!
4Q19 Cyclopropyl
4Q19 Cyclobutyl
4Q19 Cyclopenty
l 4Q19 Cyclohexy
l 4Q19 C6H3CII□
4Table 3 (continued) QI R6n Q19 C611sC(0)
4Q19 Cyclopropyl-CHz
4Q19 Cyclobutyl-CH
z 4Q19 Cyclopenty
l-CHg 4Q19 Cycloh
exyl-CHz 4Q19H
C(0) 4Q19 Me
C(0) 4Q19 CtC
(0) 4Q19 PrC(
0) 4Q19 1-PrC(0
) 4Q19 BuC(0)
4Q19 1-BuC(0)
4019 5ec-BuC(0)
4Q19 t-Buc(0)
4Q19 PenC(0)
4Q19 l1exC(0)
4Q19 MeSOt
4Q19 EtSO□
4Table 3 (continued) QI R6n Q19 Pr5O* 4Q1
9 1-Pr5Ot 4Q19
MeNH5Oz 4Q19
(Me) JSOg 4Q19
MeNHC (0) 4Q19
(Me) zNC(0) 4Q19
MeOC(0) 4019
[! tOc(0)
4Q19 Pr0C(0)
4Qll II
2011 H3 Qll II 4Qll
Etc(0) 2Qll
EtC(0) 3011
EtC(0)
4012 H2 Q12 II 3Q12
H4 Table 3 (continued) QI2 EtC (0) 2012
Etc(0)
3Q12 Etc(0) 4QI4
II 2 Q14 II 3 Q14 H4 014Etc(0)
2Q14 1Etc(0) 3
Q14 EtC(0) 4Q16
II 3 Q16 H4 Q16 EtC(0) 2Q16
Etc(0) 3Q16 Etc(0)
4Q21 H2 G21 II 3 Table 3 (continued) Q21 EtC(0) 2Q
21 EtC(o) 3Q2
1 EtC(0) 4024
If
2024 H3 Q24 +1 4Q24
EtC(0) 2Q24
Etc(0) 3024
EtC(0) 4026
H2 Q26 H3 Q26 H4 026EtC(0)
2q26 EtC(o)
3Q26 EtC(0) 4
Q28 II 2Q2
8 II 3rd 3rd
Table (continued) QI R6n (128EtC ((1) 2G28
Etc(0) 3G28
EtC(0), 4Q30
H2 Q30 H3 Q30 II 4Q30
EtC(0) 2Q30
Etc (0) 3Q30
EtC(0) 4031
II 2Q31
11 3Q31 H4 Q31 1Etc(0) 2Q
31 EtC(0) 3Q3
1 EtC(0) 4Ω33
II 2Q33
++ 3033 I
I 4 Table 3 (continued) Q33 Etc (o> 2033
EtC(0)
3Q33 Etc(0) 4Q
84 H2 Q84 H3 QB4 +1 4 Q84 EtC(0) 2Q84 1
EtC(0) 3'Q84 EtC(0
) 4Q85 H2 Q85 II 3 085 H4 Q85 EtC(0) 2085
EtC(0) 3G85 1EtC(0)
4G86 ++ 3 Q86 II 4 Table 3 (continued) QI R6n Q86 EtC(0) 21
86 Etc(0) 3Q8
6 EtC(0) 4Q87
H2 Q87 II 3Q87
Etc(0) 2087
Etc(0) 3087
Etc(0) 4Q88
H2 Q88 H3 Q88 H4 Q88 Etc(0) 2(
188Etc(0) 3088
Etc(0) 4Q89
II 2Q89 H3 Q89 II 4th 3rd
Table (continued) QI R6n Q89 EtC(0) 2Q
89 EtC(0) 308
9 EtC(0) 4 (hereinafter
, margin) When applying the compound of the present invention as an agricultural and horticultural herbicide,
Generally, a suitable carrier such as clay, talc, base
A solid carrier such as tonite or diatomaceous earth, or water or alcohol
(methanol, ethanol, etc.), aromatic hydrocarbons
(benzene, toluene, xylene, etc.), chlorinated hydrocarbons
ethers, ketones, esters (ethyl acetate, etc.)
), acid amides (dimethylformamide, etc.), etc.
It can be applied in combination with the body, optionally with emulsifiers,
Adding dispersants, suspending agents, penetrating agents, spreading agents, stabilizers, etc.
Liquid, emulsion, wettable powder, powder, granule, flowable, etc. as desired
It can be put to practical use in the following dosage form. Moreover, the compound of the present invention
If necessary, other herbicides and various other herbicides may be used during formulation or spraying.
It may be applied in combination with insecticides, fungicides, synergists, etc.

As for the type of herbicide to be mixed, for example, the Farm Chemicals Handbook (Farn+ Chemica
lsllandbook), 73rd edition (1987). The amount of the applied drug varies depending on the application situation, application time, application method, target grass species, cultivated crops, etc., but in general, the appropriate amount of active ingredient is about 0.01 to 10 kg per hectare.

Next, examples of formulations of herbicides containing the compound of the present invention as an active ingredient will be shown, but the invention is not limited thereto. In addition, in the following formulation examples, "part" means part by weight.

Hydrating agent Compound of the present invention Na 1・-・-・・・・・・・
...--60 copies of Sieglite P F P ---
------ −・・−−
--~ 5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (anti-caking agent) -2 parts (Mixture of surfactant and white carbon: Shionogi & Co. ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.

Nα1 -・・−・−・−・・−・・−
・−1,5 part xylene ・−−
−−−−−−−・−−m−−・78.5 parts N, N
-Dimethylformamide...-15 parts Trupol 2680--5 parts (
Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) The above is mixed uniformly to form an emulsion.

L-Kinbanyu Flowable Compound of the Invention Nα1-・・・・・・−−−−・・
・-40 copies Ageli Seal S-710-・-・−−−−
・---10 parts (nonionic surfactant: Kao Q1 brand name) Lunox 100OC・---
・0.5 part (Anionic surfactant: Toho Chemical ■Product name)
1% rhodobol water −−−−−1−−・・−・・−・
-...-20 parts (thickener: Loos-Boulin product name)
Water ・−−1−・・・−・−・−−−−・
------------- 29.5 parts or more are mixed uniformly to form a flowable agent.

When used, the above-mentioned wettable powders, emulsions, and flowable preparations are diluted 50 to 1000 times with water and sprayed at an amount of active ingredient of 0.01 kg to 10 kg per hectare.

The compound of the present invention can be applied to control various weeds in agricultural and horticultural areas such as fields, paddy fields, orchards, as well as in non-agricultural areas such as playgrounds, vacant lots, and railroad tracks. Although there are differences depending on the application period, application method, target grass species, cultivated crops, etc., the appropriate amount of active ingredient is generally about 0.01 to 10 kg per hectare.

Next, the herbicidal effects of the compounds of the present invention will be specifically explained by giving test examples.

Weeding effect test under warm water conditions Alluvial soil was placed in a 115,000 are Hugner pot, then water was added and mixed to create a warm water condition with a water depth of 4 cm. Seeds of Japanese grasshopper, broad-leaved weeds (Japanese chinensis, azalea, and Kikashigusa), and firefly were mixedly sown in the pots described above, and tubers of Urticaria japonica and Cyperus spp. Furthermore, rice seedlings at the 2- to 3-leaf stage were transplanted. Plants were grown in pots in a greenhouse at 20 to 30°C, and on the 3rd day after sowing or 144th day after sowing, a diluted drug solution was dropped onto the water surface using a measuring pipette at a predetermined dose.

Four times after dropping the chemical solution, the herbicidal effect on various weeds was investigated according to the following criteria. Table 4 shows the results of the herbicidal effect test performed on the third day after sowing, and Table 5 shows the results of the herbicidal effect test performed on the 14th day after sowing.

Judgment Criterion 5: Weed killing rate 90% or more (almost complete death) 4.
...Weed killing rate 70-89% 3...Weed killing rate 40-69% 2...Weed killing rate 20-39% l...Weed killing rate 5-19% 0...Weed killing rate 5% or less (dove) However, the above herbicide rate was determined by measuring the weight of above-ground plants in the chemically treated area and the weight of above-ground plants in the non-treated area using the following formula.

Table 4 0.05 5 5 5 5 00.1 5
5 5 5 00.4 5 5 5
5 00.1 3 0 0 0 00.8
The structural formulas of the 50010 test compound and comparative compound are shown below.

Compound inhibition 1 Table 5 0.253330 1.655550 0.400000 3.250000 Limb plate 2l Wheat growth inhibition test Fill a polyethylene pot with an inner diameter of 1lcI11 with field soil and sow wheat (variety: Norin No. 61) and grown in a glass chamber. At the two-leaf stage, an emulsion of the compound of the present invention and an aqueous solution of the comparative compound CCC (chlormequat) were diluted to a predetermined concentration and sprayed on the foliage.

After the treatment, the plants were grown in a glass room, and the height of the fifth leaf of the first sheath at the fifth leaf stage was measured on the 20th day.

The results are shown in Table 6. The numerical values of the height of the fifth leaf sheath firstborn and fifth leaf in the drug-treated plots in Table 6 are relative values when the untreated plot is taken as 100.

Table 6 kl 2000 58 CCC200084 Untreated group 100 The structural formula of the comparative compound is shown below.

Claims (3)

[Claims] (1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, Q_1 and Q_2 are each independently, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲Mathematical formulas, chemical formulas , tables, etc.▼ are shown. R_1, R_2, R_3, R_4 and R_5 each independently represent a hydrogen atom, a halogen atom, a trifluoromethyl group, a difluoromethoxy group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms. show. R_6 and R_7 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms, or 1 carbon atom.
An alkyl group having 1 to 2 carbon atoms which may be substituted with an alkoxy group having 1 to 3 carbon atoms, an alkyl group having 1 to 2 carbon atoms which may be substituted with a thioalkoxy group having 1 to 3 carbon atoms, carbon Alkyl group having 1 to 2 carbon atoms which may be substituted with alkylamino group having 1 to 3 atoms, cycloalkyl group having 3 to 6 carbon atoms, benzyl group which may be substituted with halogen atom, halogen A benzoyl group which may be substituted by an atom, an alkyl group having 1 to 2 carbon atoms which may be substituted by a cycloalkyl group having 3 to 6 carbon atoms, a -C(O)-R_6 group (however, R
_6 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. ), -S(O)
_2R_9 group (R_9 represents an alkyl group having 1 to 3 carbon atoms or a phenyl group optionally substituted with a halogen atom or a methyl group), -S(O)_2NR
_5(R_9) group (however, R_8 and R_9 have the same meanings as above), or -C(O)N(R_8)(R
_9) group (However, R_8 and R_9 have the same meanings as above), R_7 and Q_2 may be connected by an alkyl chain having 2 to 4 carbon atoms, and X represents an oxygen atom or a sulfur atom. show. ] A compound represented by (2) A selective herbicide containing the compound of claim (1) as an active ingredient. (3) A plant growth regulator containing the compound of claim (1) as an active ingredient.