JPS63170365A - Pyrazole derivative, its production and selective herbicide containing said derivative - Google Patents

Abstract

NEW MATERIAL:The compound of formula I {X is (halo)alkyl, halogen or NO2; Y and Z are H, alkyl or halogen; R is alkyl; n is 0-2; Q is H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl, cyanomethyl, group of formula II [A is H or alkyl; m is 0 or 1; B is (substituted) phenyl or alkyl] or organic acid residue}. EXAMPLE:1-Methyl-4-(2-methyl-3-fluoro-4-methylthiobenzoyl)-5-hyd-roxyp yrazole. USE:A selective herbicide. PREPARATION:The compound of formula I can be produced by reacting 1- methyl-5-hydroxypyrazole of formula III with a compound of formula IV (M is OH or halogen) and reacting the resultant compound of formula V with a compound of formula L-Q (L is halogen or methanesulfonyloxy).

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel 4-benzoylpyrazole derivative, a method for producing the same, and a selective herbicide containing the derivative as an active ingredient. It is useful as a drug.

[Conventional technology and problems]

BACKGROUND OF THE INVENTION A wide variety of herbicides have been put into practical use through years of research and development, and these herbicides have contributed to labor savings in weed control operations and improved productivity of agricultural and horticultural crops.

Even today, there is a demand for the development of new chemicals with more excellent herbicidal properties, and in particular, as agricultural and horticultural herbicides, they can selectively control target weeds at low doses without causing harm to cultivated crops. However, existing agents do not necessarily have suitable herbicidal properties.

On the other hand, it is already known that certain compounds of 4-benzoylpyrazole derivatives have herbicidal activity; for example, Viraplate (generic name) and Biradixifene (generic name) have been put into practical use as herbicides for rice fields. . However, although these compounds have excellent herbicidal activity as herbicides for paddy fields, their activity against weeds in upland fields is weak and they are not suitable as herbicides for upland fields, and 4-benzoylpyrazole derivatives Among them, as a field herbicide,
Superior compounds are desired.

[Means for solving problems]

The present invention relates to pyrazole derivatives represented by general formula (I): or general formula (■)
: [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. Q is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom, a lower alkenyl group optionally substituted with a halogen atom, a lower alkynyl group optionally substituted with a halogen atom, a cyanomethyl group, the following formula; In the formula, A represents a hydrogen atom or a lower alkyl group, and m is 0 or 1.
represents. B represents a phenyl group or a lower alkyl group which may be substituted with up to four same or different substituents selected from a lower alkyl group, a halogen atom, a nitro group, and a trifluoromethyl group. ) or represents an organic acid residue. The present invention relates to a salt of a pyrazole derivative represented by the above with a metal or an organic base, a method for producing the same, and a selective herbicide containing one or more of the compounds as an active ingredient.

While conducting research on the herbicidal properties of various organic compounds for the purpose of developing useful herbicides, the present inventors found that the above-mentioned compounds of the present invention were effective against grasses (Poaceae and Cyperaceae) and various broad-leaved weeds. It has an outstanding herbicidal effect against
Furthermore, the present invention was completed based on the knowledge that the present invention is substantially harmless to useful crops such as corn, turgium, and wheat.

The compounds of the present invention exhibit strong herbicidal activity in soil treatment, soil mixing treatment, and foliage treatment, while they exhibit strong herbicidal activity in soil treatment, soil mixing treatment, and foliage treatment for fi-cultured crops such as corn, tung gum, wheat, etc. Either method causes no phytotoxicity in practice, has a high degree of selectivity, and is extremely effective in controlling weeds during the cultivation of these crops. i.e. corn,
It exhibits strong herbicidal activity against noxious weeds that occur during the cultivation of trumpet gum, such as nobies, Japanese knotweed, Japanese knotweed, Japanese knotweed, Japanese knotweed, and Japanese commonweed. In particular, the herbicidal activity against the grasshopper species is extremely high, making it extremely unique. Conventionally,
Atrazine, a triazine herbicide, and alachlor and metolachlor, which are acid anilide herbicides, have been used in the cultivation of corn and trumpet gum.

However, although atrazine shows high activity against broad-leaved weeds, its activity against Poaceae is low, and its activity against Poraceae is extremely low.

On the other hand, alachlor and metolachlor have high activity against Poaceae, but low activity against broad-leaved weeds, and extremely insufficient activity against Poaceae. Therefore, it has been extremely difficult to eradicate all weed species with a single chemical treatment.

As a result of various studies, the present inventors have discovered that the compound of the present invention is effective against a wide range of weeds, and among these weeds, it is particularly effective against perennial weeds that have been particularly difficult to eradicate. They discovered this and completed the present invention.

Furthermore, the compound of the present invention has the effect that it has no phytotoxic effects on corn, turgid, and wheat and can be used safely.

The compound of the present invention has the general formula (■)=(wherein, X
, Y, Z, R, n, and Q are the same as above. ) is a pyrazole derivative represented by this compound structure, and the characteristics of this compound structure are that the 3rd position of the pyrazole ring is a hydrogen atom, and the 4th position of the benzoyl moiety is an R3 (0), , group (R, n is It has the same meaning as above.)

It has been known that 4-benzoylpyrazole derivatives have excellent herbicidal activity, and for example, virazolate (-ship name) is commercially available and is widely used in practical use. However, their practical use is limited to paddy fields, and their activity is significantly reduced under field conditions. However, as a result of many years of research into 4-benzoylpyrazole derivatives, the present inventors have found that: ■ The 3rd position of the pyrazole ring is a hydrogen atom; ■ The 2nd position of the benzoyl moiety is a suitable substituent X (X has the same meaning as above) ■ The 4th position of the benzoyl moiety is substituted with RS (0)I, the group (R,
n has the same meaning as above).

It has been found that when the above conditions (1) to (2) are simultaneously satisfied, strong herbicidal activity is exhibited under field conditions in soil treatment, soil mixing treatment, and foliage treatment.

Furthermore, these compounds can be safely used in crops such as corn, tungum, and wheat at practical dosages without causing any phytotoxicity.

The compounds of the present invention can be easily synthesized, for example, by any of the following reaction formulas.

th H3 C11゜ " C) lz C.I.

■ (Jh lh CH.

(In the formula, R,
represents 1 or 2. Furthermore, MIIP is CH3CIl
:1 and can be represented by any structural formula. Further, DCC represents N,N'-dicyclohexylcarbodiimide. ) Reaction formula (1) is a reaction between benzoic acid having an appropriate substituent and MII.
P(1-methyl-5-hydroxypyrazole), DC
Represents the reaction to obtain 4-benzoyl-5-hydroxypyrazole in the presence of C(N,N'-dicyclohexylcarbodiimide) and a base in an inert solvent.

DCC is 1.0 to 1.5 times the mole of benzoic acid and FIHP, and any solvent may be used as long as it is inert to the reaction.
In particular, tertiary-butyl alcohol, tertiary-amyl alcohol, isopropyl alcohol, etc. are excellent. Although a base is not necessarily required, its use generally improves the yield. There are no particular limitations, but potassium carbonate, sodium carbonate, etc. are excellent. The reaction temperature can be anywhere from room temperature to the boiling point of the solvent, but it is 50°C to 10°C.
A temperature of about 0°C is desirable.

The reaction time is usually about 0.5 to 20 hours.

Reaction formula (2) shows a reaction between hendiyl chloride having an appropriate substituent and MHP to form a benzoyl ester of MHP, which is then rearranged to form a 4-benzoyl compound.

Benzoyl esterification uses inert solvents (aromatic hydrocarbons, fatty acid esters, halogenated hydrocarbons,
Ethers, acetonitrile, dimethyl sulfoxide,
N,N'-dimethylformamide, etc.) or in a two-phase system or mixed system of these with water, using a suitable dehydrochlorinating agent (inorganic bases such as caustic soda, caustic potash, sodium bicarbonate, etc., pyridine, triethylamine, etc.). organic base)
This is usually achieved in 10 minutes to 5 hours at room temperature to 100°C.

The rearrangement reaction is achieved using a Lewis acid or base, typified by anhydrous aluminum chloride. Potassium carbonate, calcium hydroxide, sodium carbonate, etc. are used as the base.

Both the Lewis acid and the base are usually used in 1 to 10 times the molar amount.

Although a solvent is not particularly required, it is inert to the reaction, and one with an appropriate boiling point may improve operability, yield, etc. Suitable examples include dioxane and diglyme.

Reaction temperature is usually 50 to 150°C, reaction time is 15 minutes to
It is 10 hours.

Reaction (3) is a reaction between 4-benzoyl-5-hydroxypyrazole and halides, methanesulfonic acid ester or p-
) Shows the reaction of condensing with luenesulfonic acid ester.

It is desirable to use 1 to 3 times the mole of the dehydrohalogenating agent in this reaction. Examples of the dehydrohalogenation agent include inorganic bases such as caustic soda, caustic potash, sodium carbonate, sodium bicarbonate, and potassium carbonate, and organic bases such as pyridine and triethylamine.

The solvent is not particularly limited as long as it is inert to the reaction, and may include aromatic hydrocarbons, aliphatic esters, halogenated hydrocarbons,
Ethers, ketones, aliphatic hydrocarbons, acetonitrile, dimethyl sulfoxide, dimethyl formamide, etc. can be widely used.

The reaction temperature can be arbitrarily selected from room temperature to the boiling point of the solvent, and the reaction time is usually about 30 minutes to 30 hours.

Reaction (4) shows a reaction in which sulfoxide or sulfone is obtained by oxidizing the sulfide at the 4-position of the benzoyl moiety with a suitable oxidizing agent.

Examples of the oxidizing agent used include hydrogen peroxide, halogens, hypochlorites, organic peracids such as methachloroperbenzoic acid and peracetic acid, oxygen, manganese dioxide, chromic acid, and nitric acid.

Sulfoxide or sulfone can be selectively obtained by selecting the oxidizing agent and reaction conditions used.

The reaction (5) shows a reaction in which 4-benzoyl-5-hydroxypyrazole is converted into a 5-chloride with a chlorinating agent and then condensed with a suitable alcohol or acid.

Examples of the chlorinating agent include phosphorus oxychloride, phosphorus pentachloride, and thionyl chloride.

As the solvent, a wide range of solvents inert to the reaction such as dimethylformamide can be used, but no solvent may be used.

The reaction temperature is preferably about 30 to 150°C, and the reaction time is about 30 minutes to 10 hours, but the addition of a dehydrohalogenating agent may shorten the time and improve the yield.

For condensation reactions with alcohols or acids, a dehydrohalogenating agent is added.

Dehydrohalogenation agents include caustic soda, caustic potash, sodium carbonate, potassium carbonate, sodium alkoxide,
A base such as sodium hydride is used.

The solvent is a solvent inert to the reaction (e.g. aromatic hydrocarbons,
(ethers, ketones, N,N'-dimethylformamide, etc.) can be used, and the temperature can be between room temperature and the boiling point of the solvent.

Next, the present invention will be described with specific examples.

However, the present invention is not limited to these.

[Example 1] Synthesis of 1-methyl-4-(2-methyl-3-fluoro-4-methylthiobenzoyl)-5-hydroxypyrazole 0.88 of 1-methyl-5-hydroxypyrazole was added to 20 ml of tertiary amyl alcohol. After dissolving, 1.5 g of 2-methyl-3-fluoro-4-methylthiobenzoic acid,
N,N'-dicyclohexylcarbodiimide 1,9
g, and 0.8 g of anhydrous potassium carbonate, and then heated to 70°
The mixture was heated and reacted with C for 8 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure, and 50 nl of a 5% aqueous potassium hydroxide solution and 30 ml of chloroform were added and stirred. After filtering off insoluble matter, the aqueous layer was separated, washed with 20 m2 of chloroform, and then acidified with hydrochloric acid.

The precipitated crystals were separated by filtration, washed three times with water, and then dried to obtain 1.5 g of the title compound. This was recrystallized from ethanol to obtain 1.1 g of the title compound.

Melting point 148-150°C [Example 2] 1-Methyl-4-(2,3-dimethyl-
Synthesis of 5-hydroxypyrazole (4-methylsulfonylbenzoyl) In Example 1, 1.5 g of 2-methyl-3-fluoro-4-methylthiobenzoic acid was replaced with 3.4 g of 2,3-dimethyl 4-methylsulfonylbenzoic acid. , 1-methyl-5-
The title compound 3 was treated in exactly the same manner except that hydroxypyrazole, tert-amyl alcohol, N,N'-dicyclohexylcarbodiimide, anhydrous potassium carbonate, 5% aqueous caustic potassium solution, and chloroform were each used 2.35 times more. 1g was obtained.

Melting point 208-211°C [Example 3] Synthesis of 1-methyl-4-(2-chloro-3-methyl-4-methylsulfonylbenzoyl)-5-hydroxypyrazole 2-chloro-3-methyl-4-methyl Using 3.7 g of sulfonylbenzoic acid, the same treatment as in Example 2 was carried out on the same scale to obtain 3.2 g of the title compound.

Melting point 228-230°C [Example 4] Synthesis of 1-methyl-4-(2-methyl-4-methylsulfonylbenzoyl)-5-hydroxypyrazole Hydrochloride of 1-methyl-5-hydroxypyrazole 4.0
g, 60 mjl of an aqueous solution containing 4.0 g of 85% caustic potassium
! dissolved in After further adding 60 mA of chloroform,
2-Methyl-4 so that the temperature under water cooling does not exceed 10°C.
- 7.0 g of methylsulfonylbenzoyl chloride was added dropwise. After completion of the dropwise addition, stirring was continued for 3 hours at room temperature and 3 hours at 50°C, and then the chloroform layer was separated and the solvent was distilled off under reduced pressure. 5 ml of 1°4-dioxane and 7 g of anhydrous potassium carbonate were added to the residue, heated to 120°C with stirring, and maintained at that temperature for 4 hours.

Next, the mixture was allowed to cool to 90°C, and 50 mf of water was added to dissolve it. After being allowed to cool to room temperature, it was acidified with hydrochloric acid. The obtained crystals were collected by filtration and then recrystallized from ethanol to obtain the title compound 5.
1g was obtained.

Melting point 231-233°C [Example 5] Synthesis of 1-methyl-4-(5-fluoro-2-methyl-4-methylsulfonylbenzoyl)-5-benzyloxypyrazole 5-fluoro-2-methyl-4- Using 3.5 g of methylsulfonylbenzoic acid, the same procedure as in Example 2 was used to obtain 1.
2.6 g of -methyl-4-(5-fluoro-2-methyl-4-methylsulfonylbenzoyl)-5-hydroxypyrazole was obtained.

Using 1.2g of these, 25IIl11 of benzene and 0.5g of triethylamine were added, followed by 0.5g of benzyl bromide.
8 g was added and heated under reflux for 4 hours. Cool condensate 301 to room temperature
After adding 111 and dissolving the precipitated crystals, the benzene layer was separated, washed successively with 5% sodium bicarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.

The obtained complex was purified by silica gel chromatography (eluent: benzene) to obtain 1.3 g of the title compound.

Melting point 147-148°C [Example 6] 1-methyl-4-(2-isopropyl-4
-Methylsulfonylbenzoyl)-5-hydroxypyrazole Dissolve 10 g of methyl-4-(2-isopropyl-4-methylthiobenzoyl)-5-hydroxypyrazole in 5 ml of acetic acid, and add 2 ml of 35% hydrogen peroxide. After stirring at room temperature for 3 hours, the mixture was added to ice water. Further, 30 ml of chloroform was added and the mixture was vigorously stirred, and then the chloroform layer was separated. After washing twice with water, chloroform was distilled off. Purification by silica gel chromatography yielded 0.8 g of the title target compound.

Next, Tables 1 to 3 show compounds synthesized according to the above examples. However, the present invention is not limited to these.

Chapter 1 Table C1(.

Compounds represented by Table 1 Nq, X Y Z RQ I C12Me II Me H2CI
Me H, Me Bz3 CI
Me HMe Ts4 CE Me
HMe Me5 CI Me tl
Me Phe8 C12Me 1+
Me Me9 Cf2 Me HMe
AMBlo Cf2 Me HMe
0MB11 CI Me HMe
0CB12 CI FIe HMe CY
M13 CI Me HMe B2O3
3Ce Me HMe PMP15 C
j! Me It Me B516
(4Et HMe H17CI Et
II Me Bz18 CE Et
HMe Ts19 Cf Et H
Me Me20 CI Et HMe
Phe21 Cf Et l(Me
Prg22 CI! , Et HMe Al
123 Cf2 Et II Me
Me24 CI Et HMe AM
B25 CI Et 11 Me
0MB26 CI Et HMe 0C
B27 Cf Et II Me
CYM28 CI Et HMe BZ
O29CI! Et HMe PMP30
CE Et H Majesty BS Table 1 (
Continued) No, X Y Z
RH31 Isao HH Hase 11 32 Me HHMe Bz3
3 Me HIt Me
TaS2 Me HHMe
Me35 Me HHMe
Phe36 Me HHMe
Prg37 Me Hl! M
e Al138 Me Htl
Me Me39 Me
HHMe AMB40 Me
HHMe 0MB41 Me
HHMe 0CB42 Me
HHMe CYM43 Me
HHMe B2O33Me HH
Me PMP45 Me HH
Me B546 Me Me
HMe ) 147 Me
Me HMe Bz48
Me Me HMe Ts4
9 Me Me HMe
Me50 Me Me H
Me Phe51 Me Me
HMe Prg52 Me
Me HMe Al153
Me Me HMe
Me54 Me Me HMe
4MB55 Me Me
HMe 0MB56 Me
Me HMe 0CB57
Me Me HMe CY
M58 Me Me HMe
BZO59Me Me HM
e PMP60 Me Me
HMe BS Table 1 (continued) NO, X Y Z RQ
61 Me Et II
Me H62Me Et
II Me Bz63
Me Et HMe TaS
4 Me Et HMe
Me65 Me Et H
Me Phe66 Me Et
HMe Prg67Me
Et HMe' Al168 M
e Et HMe Me69
Me Et HMe
4MB70 Me Et H
Me 0MB71 Me Et
HMe 0CB72 Me
Et HMe CYM73
Me Et HMe
BZO74Me Et II
Me PMP75 Me
Et HMe B576C
I HF Me H77C
f2 HF Me Bz7
8 CI HF Me
Ts79 CI HF
Me Me80 Cf2 tl
F Me Phe81
CI HCI Me
H82C1HCI Me Bz83
CI HCRMe TaS4
C1) I Cjl! Hase
翫85 Cjl! HCf2
Me Phe86 Cf2
Me F Me H8
7Cf Me F Me
Bz88 Cf Me
F Me TaS9 Cf
2 Me F Me
Me90 CI Me F
Me Phe Table 1 (continued)
) No, X Y Z
RQ91 CI Me C4M
e H92 (4 CI Me
Bz93 Cjl! Me
CI Me Ts94
CI Me Cf Me
Me95 (4Me C1, M
e Phe96 Cj! Et
F Mell97
Cf2 Et F Me
Bz98Cj! EtF
MeTs99 CI Et
F Me Msloo C
I Et F Me
Phelol C1, Et Cj!
Me H102CI Et
CI Me Bz103
Cf2 Et CI Me
Ts104 Cf Et
Cj! MeMe105C
JQ Et CI Me
Phe106 Me HF
Me H107Me HF
Me Bz108 Me H
F Me Ts109 Me
HF Me Msllo
Me HF Me Phel
ll Me HCI Me
H112Me HCI Me
Bz113 Me It
CI Me Ts114 Me
HCI Me Me115
Me HCf2 Me
Phe116 Me Me F
Me H11? Me
Me F Me Bz118
Me Me F Me
Ts119 Me Me
F Me Me120 M
e Me F Me
Phe Table 1 (continued) No, X Y Z
RH1SOC1'Me Me Me
H Table 1 (continued) No, X Y Z
RQ166 Me HMe
Me H176Me Et
Br Me H2SOMe
Et Et Me H 1st
Table (continued) NαX Y Z RQ181
Me Et Et M
e Bz182 Me Et
Me Me HfB2 M
e Et Me Me
Bz184(1/!HF EtH 185Cf H(/!Et
H186Cf Arm F Et
H1O7CI Me CI
2 Et HfB2 CI2
Et F Et H1
89C/! Et (4Et
II190 Me HF E
t H191Me HCj!
Et H192Me Me
F Et H193Me
Me Cf Et H194
Me Et F Et
H2O6(4Et If Pr(
i) It210 Me HHPr
(i) H Table 1 (continued) No, X Y Z RQ
214 Me Me HPr(i
) t1215 Me Me
HPr(i) Bz216 Me
Et It Pr(n)
H217Me Et HPr(n)
Bz218 Me Et
tl Pr(i) H219Me
Et HPr(i) Bz22
0 CI Cjl! HMe
H221CI CI HMe
Bz222 C1CI HMe
Ta223 CI CI
II Me Ms224C
I CI HMe Phe2
25 CI Br HMe
H226CI2 Br HMe
Bz227 CI! , Br HM
e Ta228 Cj! Br
It Me Ms229
CI Br HMe P
he230 CI F HMe
H231CA F HM
e Bz232 CI F
HMe Ta205 CI
F HMe Ms234 (
4F HMe Phe235
Me CI HMe H23
6Me C14, HMe Bz237
Me CI II
Me Ta238 Me CI
HMe Ms239 Me
C111Me Phe240Me
Br HMe HTable 1
(continued) Na, X Y Z RQ24
1 Me Br It
Me Bz242 Me Br
HMe Ts243 Me
Br tl Me Ms
244 Me Br HMe
Phe245 Me F
HMe H246Me F
HMe Bz247 Me F
HMe Ts248 Me
F HMe Ms249 M
e F HMe Phe25
0 CI C1tl Et
H251CI Br HEt
H252CIF HEtH 253Me C4) I Et
H254Me Br HEt
H255Me F HEt
H256CI2 Cff F
Me H257C4 (4 (4 rods)
H 258CI Br F Me
H259CI Br C4
Me H2SOCI2 F
F Me H261CI F
CI Me I262
Me (4F Me H
263rd Order cz cI! , Isao
H264Me Br F
Me H265Me Br
CI Me H266Me
F F Me H26
7Me F C4Me H2
68C1I HMe H269CI
2 I HMe Bz270
CI Pr(n) HMe
H Table 1 (continued) No, X Y Z
RQ277 Me Pr(n)
HMe Bz280 Cj! I
F Me H286M
e I F Me
H287Me I CI
Me I288 Me Pr
(n) F Me H289
Me Pr(n) Cf Me
H290Me Pr(i)
F Me H291Me P
r(i) CI Me H29
2Et HHMe II293
Et HHMe Bz294 E
t It HMe Ts2
95 Et HHMe Ms29
6 Et HHMe Phe29
7 Et HHMe Prg29
8 Et HHMe Al129
9 Et ) I HMe
Me300 Et
HHMe AMB Table 1
(continued) No, X Y Z
RQ301 Et HHMe
0MB502 Et HHMe
0CB303 Et HHMe
CYM304 Et HHMe
BZO305Et It HMe
PMP306 Et)I
HMe B5307 Pr(i)
HHMe H3O8Pr(i)
HHMe Bz309 Pr(i)
HHMe Ts310 1'r(i)
HHMe Ms311 Pr(i)
HHMe Phe312 Pr(i
) If HMe Prg3
13 Pr(i) HHMe Al
1314 Pr(i) HHMe
Me315 Pr(i)
HHMe Al1314P
r(i) HHMe 0MB517
Pr(i) If HMe
0CB318 Pr(i) HI
Me CYM319 Pr(i)
HHMe BZO320Pr(i)
HHMe PMP321 Pr(i)
II HMe B5322
Et HF Me H
323Et tl F
Me Bz324 Et HF
Me Ts325 Et
HF Me Ms326
Et 11 F Me
Phe327 Et HCI
Me H328Et HCf
Me Bz329 Et
HCI Me Ts330 E
t HCI Me Me No.
1 Table (continued) No, X Y Z
RQ331 Et HCI M
e Phe332 Pr(i) I
f F Me H333Pr
(i) II F Me
Bz334 Pr(i) HF
Me Ts335 Pr(i)
II F Me Ms3
36 Pr(i) HF Me
Phe337 Pr(i) HCI
Me H338Pr(i) H
CI Me Bz339 Pr(
i) HCI Me Ts34
0 Pr(i) HC1Me Ms
341 Pr(i) HCI Me
Phe342 Et HBr
Me H343Et HBr
Me Bz344 Et
HI Me H345Et
HI Me Bz346
Et HEt Me H3
47Et HEt Me B
z348 Et HMe Me
H349Et HMe Me
Bz350 Pr(i) HBr
Me H351Pr(i)
HBr Me Bz352 Pr
(i) HI Me H35
3Pr(i) HI Me
Bz354 Pr(i) HEt
Me H355Pr(i) tl
Et Me Bz356P
r(i) HMe Me H3
57Pr(i) HMe Me
Bz358 Et Me II
Me H359Et Me
FMeI360
Et Me CI Me,
H Table 1 (continued) No, X Y Z RQ Table 1
(continued) NO, X Y Z R [1st
1 Table (continued) Na X Y Z R
Q450 Et Pr(i) CI
Men Table 1 (Continued) 隘X Y Z I?
Q478 Pr(n) Ht(Me
Ta205 Pr(n) tl
II Me Ms480
Pr(n) II It M
e, Phe Table 1 (continued) No, X Y Z
RQ481 Bu(n) H11Me
H4B2 Bu(n) HHMe
Bz483 Bu(n) HII
Me Ts484 Bu(n)
)I)I Me Ms4
85 Bu(n) HHMe Ph
e486 Br HIf Me
H487Br II HMe
Bz488 Br If
HMe Ts489 Br
H) I Me Ms490 Br
HHMe Phe491 F
HHMe H492F HH
FIe Bz493 F HHM
e Ts494 F Hl(Me
Ms495 F HIt
Me Phe496 Pr(n)
HF Me H497Pr(n)
HCI Me H498Pr
(n) If, Br Me
H499Pr(n) HI Me
ll500 Pr(n) HEt
Me H3O1Pr(n) H
Me Mell502 Bu(
n) HF Me H3O3B
u(n) HCjl! Me
H3O4Bu(n) HBr l'le
I(505Bu(n) Hr
Me H3O6Bu(n) HEt
Me H3O7Bu(n) H
Me Me H3O8Br
HF Me H3O9Br
HC1! , Me ) 1510 Br
HBr Me tl Table 1
(continued) NCLX Y Z RQ, 5
12 Br HEt Me
H513Br tl Me
Me H514F )l
F Me ) 1515 F
HC1l Mell516
F II Br Me
H517F HI Me
H518F HEt Me
H519F HMe Me
H520Pr(n) Me HM
e H521Pr(n) Me
F Mell522 Pr(
n) Me CI Me
H523Pr(n) Et HMe
ll524 Pr(n) Et
F Me H525Pr(n
) Et (II, Net(
526Bu(n) Me HMe
H527Bu(n) Me F
Me H528Bu(n) Me
Cj2 Me H529B
u(n) Et HMe H5
30Bu(n) Et F M
e H531Bu(n) Et
Cf Me H532Br
Me HMe ll533 B
r Me F Me
ll534 Br Me (4
Me H535Br Et
11 Me II536 Br
Et F Me 1
1537 Br Et Cj!
Me H538F Me
HMell539F
Me F Me H540F
Me CI Me
H Table 1 (continued) N (L X Y Z RQ541 F
Et II Me H542F
Et F Me H543F Et
CI Me H544Pr(n) C
I HMe H545Pr(n) Br
HMe H546Pr(n), F HM
e H547Pr(n) I HMe
H548Pr(n) Pr(n) It Me
H549Pr(n) Pr(i) HMe
H550Bu(n) (i!, HMe H5
51Bu(n)Br)lMe'
A352 Bu(n) F HMe H5
53Bu(n) T HMe H554Bu
(n) Pr(n) HMe ll555
Bu(n) Pr(i) II Me H
556Br Cj! )I Me'
A357 Br Br t(Mell
558 Br F HMe H559B
r I HMe H560Br Pr
(n) II Me H561Br P
r(i) l(Me ll562 F C
j! HMe H563F Br H
Me H564F F HMe H5
65F I HMe ll566 F
Pr(n) HFle H567F P
r(i) HMe ll568 1 HHM
e H 5691HF Mell 570 1 II (4Me H 1st
Table (continued) NIlX Y Z RQ5
71 1 HBr FIe
'd572 I HI
Me H5731HEt
H5741HMe Me H5751
Me II Me H576
1Me F Me H577
I Me CI Me
H578I Me Br
Me H5791Me I
Me H5801Me Et
Met(581I M
e Me shame) 1582 I
Et H shame H5831Et
F Me H584T
Et CI Me l
l585 I Et Br
Me H5861Et I
Fle ) 1587 1
Et Et Me H58
8I Et Me Me
H5B9 NOz HHMe
H590Not HF Me
ll591 N(h)l
Cj! Me H592NOz
HBr Me H593NO
z HI
Me H594NOt
HEt Mell595 NO
2HMe Me ll596 N
O2Me t(Me H597NOz
Me F Me
H598Not Me CI
Mell599 NOx
Me Br Me ll60
0 Not Me I
Me II Table 1 (continued) Na X Y Z R
0601NOz Me Et
Me H602NOz Me
Me Me H603NOz
Et HMe H604NOz
Et F Me
H605No□Et CI Me
H606Not Et Br
Me H607NO2Et
I Mell608 NO
z Et Et shame
H609NOz Et Me
Me H610CF:l HHMe
H611CPa HF M
e H612CF3 HCI
Me H613CF3 HBr
Me H614CFI t(I
Me H615CFI
HEt Me H616CF:I
HMe Me H617CFz
Me HMe H618C
FI Me F Me
H619CF:l Me CI
Me H620CF3 M
e Br Me H621C
Fs Me I Me
H622CF3 Me Et
Me H623CFt Me
Me Ma H624CF
3 Et HMe H625
CF3 Et F Me
ll626 CF s E t
Cl Kan H627Ch
Et Br Me H6
28CF3 Et I Hase
H629CF2Et
E t Me H630CF :l
E t Me Me
II Table 1 (continued) NO, XYZRQ 631 I C! ! ,)l Me
H632I Br II
Me H633IF
If Me ll634 N
o□ C2H shame H635NOz
Br HMe H636NO2F
HMe H637CFI C
1tl Me H638CF3
Br HMe ll639
cFz F H shame 11640
CLM Htl Me
H641CLM Me It
Me H642CLM Et
HMe ll643 CLM
Cf111 Mell644
CLM Br HMe H
645CLM F
HMell646
CLE HHMe H647'CLE
Me II Me
H648CLE Et H shame
ll649 CLIE Cf
11 Shame ll650 CLE
Br HMe H651CLE
F HMe H652DF
MHHMe H653DFM
Me HMe H654DFM
Et H shame 11655
DFM CI HMe ll
656 DFM Br HMe
H657DFM F HMe
11658 TFE HHMe
H659TFE Me H
Me H660TFE Et
II Isao 11 Table 1 (continued) NO, X Y Z RQ66
1 TFE Cj! II
Mell662 TFEBr
HMe H663TFE F
HMe H664C111Pr(n)
, Me H665CI HPr(n)
Me Bz666 CI
HPr(n) Me Ta205
Cj! HPr(n) Me
Ms670 CI HPr(i)
Me Bz671 CI HP
r(i) Me Ta205 CI
HPr(i) Me Ms6
75 CI HBu(n) Me
Bz676 Cf It
Bu(n) Me Ta679
CI HBu(i) Me l
l680 CI HBu(i) M
e Bz681 CI2 HBu
(i) Me Ta682 CI
HBu(i) Me Ms68
3 CI HBu(i) Me
Phe684 CI HBu(s)
Me H685C111 [1u(s)
Me Bz688 CI
HBu(s) Me Phe689
CI HBu(t) Me
ll690 Cj! HBu(t)
Me Bz Table 1 (continued) Na X Y Z
RQ691 CI HBu(t)
Me Ta692 CI HBu
(t) Me Ms693 (4H
Bu(t) Me Phe694
CI Me Pr(n) Me
H695 (4Me Pr(n)
Me Bz696 CI M
e Pr(n) Me Ta6
97 C1,Me Pr(n) M
e Ms698 CI2 Me
Pr(n) Me Phe69
9 Cf Me Pr(i)
Mell700 C4Me
Pr(i) Me Bz701
CI Me Pr(i) Me
Ta702 Cf Me
Pr(i) Me Ms703
CI Me Pr(i) M
e Phe704 CI Me
Bu(n) Me H705C
j! Me Bu(n) Me
Bz706 CjQ Me
Bu(n) Me Ta707
CI Me Bu(n)
Me Ms708 Cf Me
Bu(n) Me Phe70
9 (F! Me Bu(i)
Me H710CI Me
Bu(i) Me Bz711
CI Me Bu(i)
Me Ta712 CI2 Me
Bu(i) Me Ms71
3 C4Me Bu(i) Me
Phe714 CI Me
Bu(s) Me H715CI
Me Bu(s) Me
Bz716 CI Me B
u(s) Me Ta717 C1
, Me Bu(s) Me M
s718 Cj! Me Bu(
s) Me Phe719 (4M
e Bu(t) Me ll7
20 CI Me Bu(t)
Me Bz Table 1 (continued) NαX Y Z RH721
CI Me Bu(t) Me
Ta722 C4Me Bu(
t) Me Ms723 CI
Me Bu(t) Me
Phe724 CI2 Et
Pr(n) 'Me H725C1Et
Pr(n) Me Bz72
6 R1Et Pr(n) Me
Ta727 CI Et
Pr(n) Me Ms728
C1Et Pr(n) Me
Phe729 (/! Et P
r(i) Me H730R1EL
Pr(i) Me Bz731
CI Et Pr(i)
Me Ta732 CI2 Et
Pr(i) Me Ms73
3 CI Et Pr(i)
Me Phe734 Cj!
Et Bu(n) Me H
735CI Et Bu(n)
Me Bz736 CI Et
Bu(n) Me Ta73
7 CI Et Bu(n)
Me Ms738 (4Et
Bu(n) Me Phe739
CI2 Et Bu(i)
Me H740CI Et
Bu(i)Me Rz741C
I Et Bu(i) Me
Ta742 CA Et
Bu(i) Me Ms743
CI Et Bu(i) Me
Phe744 C1, Et B
u(s) Me H745C1! , Et.
Bu(s) Me Bz74
6 CI Et Bu(s)
Me Ta747 CI E
t Bu(s) Me Ms7
48 CI Et Bu(s)
Me Phe749 CI2
Et Bu(t) Me
H750CI Et Bu(t)
Me Bz Table 1 (continued) No, X Y Z
RH752CI Et Bu(t)
Me Ms753 Cj!
Et Bu(t) Me
Phe754 Me HPr(n)
Me ll755 Me HP
r(n) Me Bz756 Me
HPr(n) Me Ta7
57 Me HPr(n) Me
Ms762 Me HPr(i)
Me Ms772 Me
HBu(i) Me Ms777
Me HBu(s) Me
Ms780 Me HBu(t)
Me Bz Table 1 (continued) N(lX Y Z RH78
3Me 11 Bu(t) M
e Phe784 Me Me
Pr(n) Me H785M
e Me Pr(n) Me
Bz786 Me Me
Pr(n) Me Ta787
Me Me Pr(n) Me
Ms788 Me Me
Pr(n) Me Phe789
Me Me Pr(i)
Me H790Me Me
Pr(i) Me Bz791 M
e Me Pr(i) Me
Ta792 Me Me
Pr(i) Me Ms793
Me Me Pr(i) Me
Phe794 Me Me
Bu(n) Me H795Me
Me Bu(n) Me
Bz796 Me Me
Bu(n) Me Ta797 M
e Me Bu(n) Me
Ms798 Me Me
Bu(n) Me Phe799
Me Me Bu(i) M
e H800Me Me B
u(i) Me Bz801 Me
Me Bu(i) Me
Ta802 Me Me
Bu(i) Me Ms803 M
e Me Bu(i) Me
Phe804 Me' Me
Bu(s) Me H805M
e Me Bu(s) Me
Bz806 Me Me
Bu(s) Me Ta807
Me Me Bu(s) Me
Ms808 Me Me
Bu(s) Me Phe809
Me Me Bu(t)
Me H810Me Me
Bu(t) Me BzTable 1 (
Continued) South, X Y Z RH81
1Me Me Bu(t) M
e Ta812 Me Me
Bu(t) Me Ms813
Me Me Bu(t)
Me Phe814 Me Et
Pr(n) Me H815
Me Et Pr(n) Me
Bz816 Me Et
Pr(n) Me Ta817
Me Et Pr(n) M
e Ms818 Me Et
Pr(n) Me Phe819
Me Et Pr(i)
Me H820Me Et
Pr(i) Me Bz821
Me Et Pr(i) Me
Ta205 Me Et
Pr(i) Me Ms823
Me Et Pr(i) M
e Phe824 Me Et
Bu(n) Me H825M
e Et Bu(n) Me
Bz826 Me Et
Bu(n) Me Ta827
Me Et Bu(n) Me
Ms828 Me Et
Bu(n) Me Phe829
Me Et Bu(i)
Me H830Me Et
Bu(i) Me Bz831 M
e Et Bu(i) Me
Ta832 Me Et
Bu(i) Me Ms833
Me Et Bu(i) Me
Phe834 Me Et
Bu(s) Mell835
Me Et Bu(s)
Me Bz836' Me Et
Bu(s) Me Ta20
5 Me EtBu(s) Me
Ms838 Me Et
Bu(s) Me Phe839
Me Et Bu(t) M
e H840Me Et B
u(t) Me Bz Table 1 (Continued)
) No, X Y Z
RQ852 CI Br Bu (
n) Me H866Me (
/! Bu(s) Me H8
67Me CI Bu(t)
Me H868Me Br
Pr(n) Me H869Me
Br Pr(i) Me
ll870 Me Br Bu (
n) Me tl Table 1 (continued) NcLX Y Z R mouth 871 Me Br Bu(i) Me
ll872 'fee Br Bu(s
) Me l+873 Me Br
Bu(t) Me H874Me F
Pr(n) Me 1f875 Me F
Pr(i) Me H876Me F
Bu(n) Me H877Me F
Bu(i) Me ll878 Me
F Bu(s) Mell879
Me F Bu(t) Me ll88
0 MeS Ht(Mell881 Me
S FIe HMe H882MeS E
t HMe H883MeS CI H
Me H884MeS Br tl M
e H885MeS FI Ma
ll886 MeSOHHMe 11887
MeSOMe HMe H888MeSOE
t II Mell889 MeSO
C1tl Me +1890 MeSOBr
HMe H891MeSOF HMe
ll892 MeSOz HHMe ll
893 MEISO2Me HMe H89
4MeSOz Et HMe +1895
MeSOz CI HMe ll896
MeSO□Br HMe ll897 M
eSOz F HMe H898EtS
HHMe H899EtS Me HMe H900Et
S Et HMe H Table 1 (continued) No, X Y Z
RQ901 EtS Cf It
Me H902EtS Br
HMe H903EtSF
Between H ll904 Pr(n)S
t(HMe H905Pr(n)S
Me HMe ll906 Pr
(n) S Et HMe H90
7Pr(n)S CI HMe
H908Pr(n)S Br HMe
H909Pr(n)S F HMe
H910Pr(g)S HHMe
H911Pr(i)S Me HMe
H912Pr(i)S Et
HMe H913Pr(i)S C1HM
e H914Pr(i)S Br
It Me H915Pr(i)S
F It Me ll
916 Ac H11Me H9
17Ac Me II Me
H918Ac Et HM
e H9198c Cj
! HMe
H920Ac Br HMe
H921Ac F HMe
H922MeOCIIz HHMe
ll923 MeOCHz Me H
Me H924MeOCHz Et
HMell925 MeOCIIg
Cfl! MeH
926MeOCL Br tl
Mell927 MeOCIIz
F It Me H928E
tOCHz It It Me
, H929EtOCIlz Me
HMe H! 130 EtOCIIz
Et)l Sea H 1st
Table (continued) Na X Y Z R
Q931 EtOC1l□ Cj2 I
I Me! (932EtOCIlz
Br II Me H
933EtOCHz F HMe
11934 CHFzOHHMe +1
935 CIIFzOMe tl
Me +1936 CIIFzOEt
HMe ll937 CllF2
OCf H side H938C11FzOB
r HMe H939CllF2OF
II Ship H940MeOH
HMe H 941MeOMe tl Me
1 (942MeOEt HMe
H943MeOCI HMe H94
4MeOBr HMe ll945
MeOF t(Me H946E
tSOHHMe ll947 EtSOM
e HMe ll948 EtS
O□HHMe H949EtSO,Me
HMe ll950 Pr(n)SO
It HMe H951Pr(n)S
OMe HMe ll952 P
r(n)SOz 11 fl Me
H953Pr(n)SOz Me
fl Me 11954 Pr
(i) SOII II! 1e
ll955 Pr(i) So Me
HMe H956Pr(i)SOz H
II Mell957 Pr(
i) SOz 'he HMe H9
58EtCOHII Me ll95
9 EtCOMe HMe H9
60Pr(n)Co HHMe H 1st
Table (continued) Na X Y Z
RQ961 Pr(n)COMe HM
ell962 Pr(i)CoH
HMe l963 Pr(i)COMe
II Me) 1964
MeOCHzCHzt(II Me
B965 MeOCIlzCllz
Me HMe 1966 EtO
It II Me 19
67 EtOMe II Me
l968 Pr(n)OIf
HMe ll969 Pr(n)OMe
HMe ll970 Pr(i
)OHHMe l971 Pr(i)OM
e II Me ll97
2 Bu(n)S HHMe 197
3 Bu(n)So HHMe ll
974 Bu(n)SOz II H
Mell975 Bu(i)S H
HMe 1976 Bu(i)So
t(HMe l977 Bu(i)SOz
HHMe 1978 Bu(s)S
II HMe ll979
Bu(s) So Htl Me
l980 Bu(s)SOz HHMe
ll981 Bu(t)S II
HMe ll982 Bu(t)S
o HHMe 1983 Bu(t)
Sow Htl Me l984
Bu(n)Co HHMe ll9
85 Bu(i)Co HHMe l
986 Bu(s)COHtl Me
l987 Bu(t)COIt
HMe 1988 EtOCIIzCl
lz HII Me l989
Pr(n)OCHz HII Me
l990 Pr(i)OCHz HHM
e H Table 1 (continued) No, X Y Z
RQ1107 (CHZ) :l
HMe l11108 -(CHz)3
- HMe Bz1109
(CH2) 3 II Me
Tslllo (Cllz) 3
HMe Msllll (C
Hz) x HMe Phe111
2 (C1lz) a HMe
B1113 (CH2)4-
HMe Bz1114 (CIl
z) a HMe Ts1115
(CHz) a I(Me
Ms1116 (C1lz) a
II Me Phe1117
(C)lz) 3F
Shame 11111B -(CHz)z -C
I Fle 111119
(CL) :l Br Me
ll1120 (CHz)z
TMel1121
(CHz) 3 Et Me
B1122 (CHZ) :l
Me Me l11123
-(CH2)4- FMe
B1124-(CL)4-CI
Me B1125 (Chz
) a Br Me t(
1126(C1(z) 4I Me
B1127-(CH2)4-Et
Me l1128 (Cl
lz) a Me Me
l1129 C1tl HPr(i)
Ts (however, 991-1106 are missing numbers) 2nd
Compounds represented by Table CH3 (hereinafter referred to as blank spaces) Table 2 Na X Y Z RQI CI
Me HMe H2CI Me H
Me Bz3 CI Me HMe
Ts4 CI Me HMe Me5
Cf Me HMe Phe6 C
l2 Me II Me Prg7
C1, Me 11 Me A118
CI Me HMe Me9 CI
Me HMe AMBlo CI M
e HMe 0MB11 CI Me
HMe 0CB12C2 H shame CY gate 13 CI Me HMe B2O33
CI Me HMe PMP15 Cf
Me HMe B516 CI
Et H-Kon l117 CI Et
If Me Bz18 CI Et
II Me Ts19 CI Et
HMe Me20 C1Et HMe
Phe21 Cf Et l! M
e Prg22 Cl2 Et HMe
Al123 CI Et HMe
Me24 CI Et HMe AM
B25, CI Et HMe 0MB
26 CI Et II Me 0
C827CI Et HMe CYM28
CI Et HMe B2O33CI
Et i(Me PMP30 Cf
Et H Order BS Table 2 (Continued) NO, X Y Z RH31
Me HIf Me I32
Me HHMe Bz33
Me HHMe Ts34
Me HII Me M
s35 Me HHMe Ph
e38 Me HIf Me
Me39 Me HHMe
AMB40 Me HHMe
0MB41 Me HHMe
0CB42, Me II
HMe CYM43 Shame HH
Chest B2O33Me It H
Me PMP45 Me HH
Me B546 Me Me
HMe H47Me Me
HMe Bz48 Me
Me HMe Ts49
Me Me HMe Ms5
0 Me Me HMe
Phe53 Me Me
It Me, Me54 Me
Me HMe AMB55
Me Me HMe
0MB56 Me Me H
Me 0CB57 Me Me
)I Me CYM58
Me Me HMe
BZO59Me Me tl
Me PMP60 Me M
e HMe BS Table 2 (continued)
) No, X Y Z
RQ61 Me E t
lI Me ll62 Me
Et HMe Bz63
Me Et HMe
Ts64 Me Et tl
Me Ms65 Me
Et HMe Phe66
Me Et HMe Pr
g67 Me Et HMe
A 1168 Me Et
HMe Me69 M
e Et
HMe AMB70 Me
Et HMe 0MB71
Me Et HMe
0CB72 Me Et H
Me CYFI73 Me E
t HMe B2O33Me
E t If Me P
MP75 Me Et HM
e B576 Ci HF
Me I77 (4HF
Me Bz78 C1ll
F Me Ts79
Cf HF Me Ms8
0 Cf! , HF Me P
he81 CA HCI Me
H82CI2 HC4 Majesty B
z83 CI If R1M
e TaS4 C1, HCI
Me Ms85 CI HC4
Me Phe86 CI Me
F Me H87CI
Me F Me
Bz88 CI Me F
Me TaS2 CI
Me F Me hs9
0 Cj! MeF
Me Phe Table 2 (continued) Nα X Y Z RQ
91 (I2 Me CF!
Mell92 CI
Me CI Me BZ9
3 CI2 Me Cj!
Me Ts94 CI
Me C4Me Ms95 C
I Me C4Me Phe
96 CI Et F
Shame ll97 Cj! Et
F Me Bz98
CI2 Et F Me
Ts99 CI Et
F Me Msloo CI
Et F Me Ph
elol Cf Et CI
Me H102C4Et CI
Me Bz103 CI
Et C1Me Ts104
(4Et C4Me Ms105
Cf! Et CI2
Me Phe106 Me HF
Me H107Me HF
Me Bz108 Me
HF Me Ts109 M
e HF Me Msllo
Me HF Me P
hell Me HCI Me
H112Me HCI M
e Bz113 Me II
CI2 Me Ts114
Me HCI Me Ms
115 Me HCj! Me
Phe116 Me Me
F Me 1+117 Me
Me F Me
Bz118 Me Me F
Me Ts119 Me
Me F Me Ms120
Me Me F Me
Phe Table 2 (continued) k X Y Z R
H123Me Me CI
Me Ts124 Me Me
CI2 Me Ms125
Me Me CI Me
Phe126 Me Et
F Me H150CI2
Me Me Me
H Table 2 (continued) No, X Y Z
RQ151 Cl3 Me Me
Me Bz152 CI
Et Br Me I
153 CI Et Br
Me Bz154 CI E
t I Me H155Cj
! Et I Me
Bz156 CI Et Et
Me H157CA Et
Et Me Bz158
CI Et Me Me
H159 (J2 Et M
e Me Bz160 Me
HBr Me H161Me
It Br Me
Bz162 Me HI Me
H163Me HI Me
Bz164 Me HEt
Me H168Me Me
Br Me H175Me
Me Me Me Bz
176 Me Et Br
Me H! 79 Me Et
I Me Bz180
Me Et Et Me
H Table 2 (continued) Na X Y Z RQ182 Me
Et Me Me I183
Me Et Me Me Bz184
c4HF Et H185 (4HCl3 Et H186CI!,
Me F Et H187Cl3 M
e CI Et H188CI Et
F Et H189CI Et
C4Et H1O0 shame I F Et
H191Me! ! C(L Et
H192Me Me F Et
H193Me Me CI Et
H194Me Et F Et H2
O2C4Me HPr(i) H2O3C1Me
II Pr(i) Bz204 Cjl
! Et 11 Pr(n) lI20
5 Cjl! Et II Pr(n)
Bz206 CI Et HPr(i)
11207 CI Et HPr(i)
Bz208 Me HHPr(n) H2
O9Me HHPr(n) Bz210 Me
HIf Pr(i) H Table 2 (Continued)
ki) NaX Y Z RQ
220 CI Cff HMe
H221CI C1tl
Me Bz222 CI CI!
, HMe Ta205 Cl3
Br HMe Bz229 CI
! , Br tl Me P
he230 CI F II
Me H231Cj! F
HMe 'Bz232 (/!
F HMe Ta236
Me Cjl! HMe
Bz237 Me C1! I
Me Ta238 FIe
CI HMe Ms239 Me
CI! , HMe Phe240
Me Br
HMet(
Table 2 (continued) No, X Y ZRQ2
41 Me Br It
Me Bz242 Me B
r It Me Ta24
3 Me Br II
Me Ms244 Me Br
HMe Phe245 Me,
F HMe H246M
e F HMe Bz24
7 Me F 1+
Me Ta248 Vessel F
H shame Ms249 Me F
HMe Phe250 Cf
(, e HEt H251
Cl3 Br II Et
H252C4F l(Et
lI253 CI HEt
11254 Me Br
HEt H255 shame F
11 E t H256C4!
Cl3 F Shame l
I257 C4CI C4 Order 11
258 C1l 13r F
Me H259CI Br
CE Me H260Cl3
F F Me
H261CI F CI
Me H262Me CI
F Me H263Me
CI C1'Me' lI264
Me Br F M
e H265Me Br C
A Me H266Me F
F Me H267M
e F Cj! Me
H268CI T tl
Me H269CI I
It Me Bz270
CA Pr(n) It,
FIe tl Table 2 (continued) Na X Y Z
RQ271 CI Pr(n)
II Me Bz272C
I Pr(i) HMe H2
73CI Pr(i) HMe
Bz274 Me I HM
e ll275 Me I
HMe Bz276 Me
Pr(n) HMe H277Me
Pr(n) II Me
Bz278 Me Pr(i)
HMe ll279 Me
Pr(i) HMe Bz280
CI2 IF Hachi
H281CI I CI
Mell282 CI P
r(n) F Me 112
83 C4Pr(n) l,e M
e ll284 CI Pr(i
) F Me H285CQ
Pr(i) CI! ,Me
ll286 FIe I F
Me ll287 Me
I CI Mell
288 Me Pr(n) F
Me H289 gate e Pr
(n) CI Mell29
0 Me Pr(i) F
Me H291Me Pr(i)
CI2 Me H292Et
HHMe H293Et
HHMeBz 294 Et HHMe Ts2
95 Et HHMe Ms29
6 Et HHMe Phe29
7 Et HHMe Prg29
8 Et HHMe Al129
9 Et It HMe
Me300 Et
HHMe AMB Table 2 (continued)
) NcLX Y ZRQ 301 Et HIt Me 0MB5
02 Et HHMe 0CB303 E
t HHMe CYM304 Et H
, HMe BZO305Et HHMe
PMP306 Et HHMe B5307
Pr(i) tl HMe H3O8P
r(i) HHMe Bz309 Pr(i)
HHMe Ts310 Pr(i) II
HMe Ms311 Pr(i) HH
Me Phe312 Pr(i) HHMe
Prg313 Pr(i)
HHMe Al1314 Pr(
i) II HMe Me315
Pr(i) tl
HMe Al1314 Pr
(i) HHMe 0MB517 Pr(i)
tl tl Me OC[1318P
r(i) HII Me CYM319
Pr(i) H11Me BZO320Pr(i
) HHMe PMP321 Pr(i)
II HMe B5322 Et HF
Me H323Et HF Me
Bz324 Et HF Me T
s325 Et HF Me Ms32
6 Et HF Me Phe327
Et HCI Me H328Et
HC1Me Bz329 Et HCI
Me Ts330 Et HCf
Me Me Table 2 (continued) Na X Y Z
RQ331 Et HCI M
e Phe332 Pr(i) H
F Me H333Pr(i)
I(F Me Bz334
Pr(i) II F
Me Ts335 Pr(i) I
f F Me Ms33
6 Pr(i) HF Me
Phe337 Pr(i) It
CI Mell338
Pr(i) HCI Me
Bz339 Pr(i) HCI
Me Ts340 Pr(i) H
(4Me Ms341 Pr(i)
II C1Me Phe342
Et II Br M
e H343Et HBr
Me Hz344 Et HI
Me I (345EL H
I Me Bz3, i6 Et
HEt Me H347E
t It Et Me
Bz348 Et HMe
Me ll349 Et HM
e Me Bz350 Pr(i
) HBr Me H351P
r(i) if Br Me
Bz352 Pr(i) HI
Me H353Pr(i)
II I Me Bz3
54 Pr(i) HEt Me
H355Pr(i) It
IEt Me Bz356 Pr
(i) ll Me Me
H357Pr(i) It
Me Me Bz358 Et
Me HMe ll359
Et Me F Me
ll360 Et Me
CI Me II Table 2 (
Continued) NQX Y Z Rl
11361 Et Me Br
Me H362Et Me
I Met(363Et)
Me Et Me
H364Et Me Me
Me H365Et Et
It Me H366Et
Et F Me 1 (
367 Et Et CI M
e It3G8 Et Et
BrMet(369Et
Et I Me
ll370 E t E t E
t Me H371Et
Et Me Me H372
Pr(i) Me HMe l
l373 Pr(i) Me F
Mell374 Pr(i)
Me CI Me
H375Pr(i) Me Br
Mell376 Pr(i)
Me I Me ll3
77 Pr(i) Me Et
Me H378Pr(i) Me
Me Me H379Pr
(i) Et HMe 138
0 Pr(i) Et F
Mell381 Pr(i)
Et ClMe H382Pr(i
) Et Br Me
ll383 Pr(i) Et
I Me H384Pr(i)
Et Et Me H3
85Pr(i) Et Me
Me ll386 Et C/!
II Add 1■387
Et Ci! , II Me
Bz388 Et Br H
Me H389Et Br
It Me Bz390EtF
H Order H Table 2 (Continued) Na X Y Z
RQ420 Pr(i) CI E
t Me h Table 2 (continued) No, X Y Z
RQ450 Et Pr(i) C
l3 Me H Table 2 (continued) NaX Y Z RQ48
0 Pr(n) HHPIe Pn
eTable 2 (continued) Ha X Y Z R
Q510 Br It Br
Me It Table 2 (continued) No, X Y Z RQ511 B
r HI Me H512Br HE
t Me H513Br HMe M
e H514F II F Me
ll515 F It CI Me
H516F HBr Me H517
F l(I Me H518F HE
t Me H519F HMe Me
H520Pr(n) Me HMe
ll521 Pr(n) Me F Me
H522Pr(n)MeCl3
Me H523Pr(n) Et tl
Me H524Pr(n) Et F
Me H525Pr(n) Et Cf!
, Me H526Bu(n) Me HMe
H527Bu(n) Me F Me
H528Bu(n) Me CI M
e ll529 Bu(n) Et HM
e H530[1u(n) Et F
Me H531Bu(n) Et Cl3
Me H532Br Me II
Me H533Br Me F M
e H534Br Me CI Me
H535Br Et HMe H5
36Br Et F Me H537
Br Et CI Mell538
F Me HMe ll539 F
Me F Me H540F
Me CI Me H Table 2 (continued) No, X Y Z RQ541 F
Et H shame H542F Et
F Mell543 F Et
CI Me H544Pr(n) C4HM
e H545Pr(n) Br II
Me H546Pr(n) F HMe
ll547 Pr(n) I It M
e H548Pr(n) Pr(n) It
Me H549Pr(n) Pr(i)
HMe H550Bu(n) CI It
Me H551Bu(n) Br HM
e ll552 Bu(n) F HMe
ll553 nu(n) I HMe
ll554 Bu(n) Pr(n) HM
e H555Bu(n) Pr(i) HMe
ll556 Br CI HMe
H557Br Br If Me
H558Br FI Me H55
9Br r It Mell560
Br Pr(n) HMe H561B
r Pr(i) HMe H562P
CI HMe H563F Br 1
1 Mell564 F F H
Me H565F I II Me
H566F Pr(n) It Me
H567F Pr(i) II Me
H5681HH Addition 11 569 I HF Mell570
1 II C4Me H Table 2 (continued)
) No, X Y Z
RQ571 I HBr Me
ll572 1 HI
Me H573I HEt
H5741HMe Me
H5751Me HMe H576
I Me F Me
ll577 I Me CI
Me H578I Me
BrF! e H5791Me
I Me H580T
Me Et Me
H581 [Me Me Me
H582I EL HMe
H583T Et F
Me H584T, Et
C1! , Me H5851Et
Br Me H586I
Et I Me l
l587 1 E t E t
Me H5881Et Me
Me H589NOz I
I HMe ll590 NOz
HF Me H591NO
z HCI Mell59
2 NOz HBr Me
H593NOz HI Me
11594 NOz HEt
Me H595NOzt(Me
Me H596NOz M
e HMe ll597 NOz
Me F Me
H598NOz Me CI
Me H599Not Me
Br Mell600N
Oz Me T Me
H Table 2 (continued) No, X Y Z R
Q601 Not Me Et
Me H602NOz Me
Me Me H603NO
2Et HMe ll604 N
o□ Et F shame
H605No□Et CIlMe H
606NOz Et Br
Mell607 Not Et
I Me 1 (608N
ot Et Et Me
H609NO2Et Me M
e H610CF3 HHMe
H611CFs)IF
Me H612CF: l H
CI! , Me H613CF3 HB
r Mell614 CF3
HI Me 11615
CF3 If Et
Mell616 CF3 II
Me Mell617
CF3 Me HMe
H618CF3 MeF
Me I (619CF, Me
CI Me H620CFz
Me Br Me
H621CF, Mer
Me 1t622 CF2
Me Et Me H623
CFz Me Me Me
ll624 CF:l Et
HMe H625CF:I E
t F Me H626C
F+ Et C1Me ll
627 CFz Et Br
Me ) 162B CF:l
Et I Me H6
29CF+ Et Et M
e ll630 CF3 Et
Me Me ItTable 2
(continued) No, X Y Z
RQ660 TFE Et HFl
e i Table 2 (continued) No, X Y Z
RQ690 (/! HBu(t
) Gate B I5z Table 2
(continued) No, X Y Z
RQ720 C1Me Bu(t)
Me 11z Table 2 (continued) Nα X Y Z
RQ750 CI Et Bu
(t) Me Bz Table 2 (continued)
) NLlX Y Z RH
751CI Et Bu(t)
Me Ta752 Cj! E
t Bu(t) Me Ms7
53 CI Et Bu(t)
Me Phe754 Me
HPr(n) Me H755Me
HPr(n) Me Bz75
6 Me HPr(n) Me
Ta757 Me HPr(n)
Me Ms758 Me
HPr(n) Me Phe759
Me HPr(i) Me
H760Me HPr(i) Me
Bz761 Me HPr(i)
Me Ta762 gate e
HPr(i) Me Ms763
Me HPr(i) Me P
he764 Me HBu(n)
Me H765Me HBu(n)
Me Bz766 Me
HBu(n) Me Ta767
Me HBu(n) Me M
s768 Me II Bu (
n) Me Phe769 Me
HBu(i) Me H770
Me HBu(i) Me B
z771 Me HBu(i) M
e Ta772 Me HBu(
i) Me Ms773 Me
HBu(i) Me Phe77
4 Me HBu(s) Me
H775Me HBu(s) M
e Bz776 Me HBu(
s) Me Ta777 Me
H' Bu(s) Me M
s778 Me HBu(s) M
e Phe779 Me HBu
(t) Me H780Me
HBu(t) Me Bz Table 2 (continued)
) No, X Y Z RH781Me
HBu(t) Me Ta782 Me
HBu(t) Me Ms783 Me
HBu(t) Me Phe784 Me
Me Pr(n) Me H785M
e Me Pr(n) Me Bz78
6 Me Me Pr(n) Me
Ta787 Me Me Pr(n) M
e Ms788 Me Me Pr(n
) Me Phe789 Me Me
Pr(i) Me 8790 Me M
e Pr(i) Me Bz791 Me
Me Pr(i) Me Ta792
Me Me Pr(i) Me M
s793 Me Me Pr(i) Me
Phe794 Me Me Bu(n
) Me H795Me Me Bu(
n) Me Bz796 Me Me
Bu(n) Me Ta205 Me
Me Bu(n) Me Ms798 M
e Me Bu(n) Me Phe7
99 Me Me Bu(i) Me
H800Me Me Bu(i) Me
Bz801 Me Me Bu(i)
Me Ta802 Me Me Bu
(i) Me Ms803 Me Me
Bu(i) Me Phe804 Me
Me Bu(s) Me ll805
Me Me Bu(s) Me Bz
806 Me Me Bu(s) Me
Ta807 Me Me nu(s)
Me Ms808 Me Me Bu
(s) Me Phe809 Me Me
Bu(υ Me H810Me Me
Bu(t) Me BzTable 2 (Continued)
) No, X Y Z
RH811Me Me Bu(t)
Me Ta812 Me
Me Bu(t) Me M
s813 Me Me Bu(t
) Me Phe814 Me
Et Pr(n) Me
H815Me Et Pr(n)
Me Bz816 Me
Et Pr(n) Me Ta
817 Me Et Pr(n)
Me Ms818 Me
Et Pr(n) Me P
he819 Me Et Pr(
i) Me H820Me E
t Pr(i) Me Bz8
21 Me Et Pr(i)
Me Ta822 Me
Et Pr(i) Me Ms
823 Me Et Pr(i)
Me Phe824 Me
Et Bu(n) Me
H825Me Et Bu(n)
Me Bz826 Me E
t Bu(n) Me Ta2
05 Me Et Bu(n)
Me Ms828 Me
Et Bu(n) Me Ph
e829 Me Et Bu(i
) Me H830Me Et
Bu(i) Me Bz83
1 Me Et Bu(i)
Me Ta205 Me E
t Bu(i) Me Ms8
33 Me Et Bu(i)
Me Phe834 Me
Et Bu(s) Me H
835Me Et Bu(s)
Me Bz836 Me Et
Bu(s) Me Ta83
7 Me Et Bu(s)
Me Ms838 Me E
t Bu(s) Me Phe
839 Me Et Bu(t)
Me H840Me Et
Bu(t) Me Bz 2nd
Table (continued) No, X Y Z
RH841Me EL nu(t)
Me Ta842 Me
Et Bu(t) Me Ms
843 Me Et Bu(t)
Me Phe844 CI
C4! Pr(n)Me
8845 C1 (4Pr(i) Me
H846Cj! CI Bu(
n) Me H847CI C
I Bu(i) Me H84
8CI CI Bu(s) Gate
e H849C4! C.I.
Bu(t)Mell850C
1Br Pr(n) Me H
851Cf Br Pr(i)
Me H852CI Br
Bu(n) Me H853CI
Br Bu(i) Me
H854CI Br Bu(s)
Me H855Cj! Br
Bu(t) Mell856
Cj! F Pr(n)
Me ll857 Cj! F
Pr(i) Me H858
CI F Bu(n) Me
ll859 CI F
Bu(i) Mell860C
I F Bu(s) Me
H861CI F Bu(t)
Me H862Me CI
Pr(n) Me H863M
e C1, Pr(i) Me
H864Me' (4nu(n) M
e H865Me Cl3
Bu(i) Me H866Me
Cj! Bu(s) Me
H867Me Cjl! Bu(t
) Me H868Me Br
Pr(n) Me H869
Me Br Pr(i) Me
H870Me Br Bu
(n) Me H Table 2 (continued) No, X Y Z
RQ871 Me Br Bu (
i) Me ll872 Me
Br Bu(s) Me
H873Me Br Bu(t)
Me ll874 Me
F Pr(n) Me H87
5 gate e F Pr (i)
Me H876Me F B
u(n) Me H877Me
F Bu(i) Me H8
78Me F Bu(s) M
e H879Me F Bu
(t) Me ll880 MeS
HHMe H881MeS
Me HMe H882MeS
Et HMe H883MeS
C1! , It Mell
884 MeS Br HMe
H88511eSF HM
e H886MeSOHHMe H 887MeSOMe HMe ll8
88 MeSOEt HMe H
889MeSOCl3 HMe H8
90MeSOBr HMe H891
MeSOF tl Me H
892MeSOz HHMe 1189
3 MeS (12Me II M
e H894MeSO2Et tl
Me H895MeSOz C
I! , HMe H896MeSOz B
r HMe H8971'IeSOt
F HMe ll898
EtS tl Hachi 118
99 EtS Me HMe
H900EtS EtH shame
H Table 2 (continued) No, X Y Z
RQ930 ELOCHz Et
HMe H Table 2 (continued) Nα X Y Z RQ
960 Pr(n) COHHMe Hth
2 Table (continued) Yang, X Y Z RQ
961 Pr(n)Co Me If
Mell962 Pr(i
) COHHMe ll963 Pr(i)
Co Me HMe ll964
MeOCHzCHz tl HMe
H965MeOCIlzCtlzMe
HMe ll966 EtOHH
Me H967EtOMe HMe
ll968 Pr(n)OHHMe
H969Pr(n)OMe HMe
11970 Pr(i)OHHMe
H971Pr(i)OMe II
Me H972Bu(n)S HHMe
H973Bu(n)SOHtl M
e ll974 Bu(n)SO2HHM
e H975Bu(i)S It
HMe ll976 Bu(i)So
HHMe H977Bu(i)SOz
II II Me H
978Bu(S)S HII Me
H979Bu(S)So II
HMe H980Bu(S)SOz HII
Me H981Bu(t)S
HHMe H982Bu(t)So [
I HMe ll983 Bu
(t) Sow! (HMe H984Bu(
n) Co HII Me ll
985 Bu(i) COfl 1!
Mell986 Bu(s)C
o 'HHMe H987Bu(t)Co
II II Me
H988EtOCIIzClh tl H
Me 1(989Pr(n)OCIlzH
HMe 1i990 Pr(i)OCHz
HHMe H Table 2 (continued) NLIX Y Z RQ11
07 (CHz) 3HMe It
1108 (C1lz) 3HMe
Bz1109-(C1lz)3-HM
e Tslllo (CHz) z
HMe Msllll
(CII2) 3 11 Me
Phe1114 (Cth) 4
It Me Ts1115
(CHHz) a HMe
Ms1116 (CHz) 4
HMe Phe Table 2 (continued) No, X Y Z
RQ1137 CI H
11Me AMB1138
CI HHMe 0MB1139
Cf HHMe 0CB1140
CI HHMe CYM1141
CI HHMe BZO114
2CI HHMe PMP1143
C1it HMe IIS [below
Margin] Table 3 Compounds represented by Cl3 (hereinafter referred to as margins) Third table stone X Y Z RQ I C1Me HMe It2 C1Me
If Me Bz3 C42Me
HMe Ts4 Cl3 Me HM
e Me5 CI Me HMe
Phe6 Cl3 Me HMe Pr
g7 CI Me
If Me
Al18 C1Me HMe Me9
CI Me HMe AM Blo
Cf Me HMe 0MB11 CI
Me HMe 0CB12 CI
Me HMe CYM13 Cl3
Me HMe B2O33CI Me
! I Me PMP15 Cf! ,Me
HMe B516 Cf Et H
Me B17 Cjl! Et HMe
Bz18 CI Bt HMe
Ts19C! ! , Et HMe Me20
CI Et HMe Phe21
CI Et It Me Prg22
Cf Et H addition Al123 (4
Et II Hase Ship 24 CI Et
HMe AMB25 CI Et
tl Me 0MB26 Cl3 E
t H shift 0CB27 (/! Et
HMe CYM28 (/! Et
H addition B2O33CI Et II M
e PMP30 (/! Et HMe
BS Table 3 (continued) No, X Y Z
RB31 Me HII Me
B32 Me HHMe
Bz33 Me tl
HMe Ts34 Me HH
Me Ms35 Me HHM
e Phe36 Me HIt
Me Prg37 Me
11 tl M
e Al138 Me H
II Me Me39 Me
II HMe AMB40
Me tl HMe
0MB41 Me HHMe
0CB42 Me HHMe
CYM43 Me tl HM
e B2O33Me HHMe
PMP45 Me It
HMe B546 Me Me
HMe H47Me Me
II Me Bz48
Me Me HMe T
s49 Me Me HMe
Ms50 Me Me
HMe Phe51 Me
Me HMe Prg52 M
e Me II Me
A1153 Me Me
HMB Me54 Me Me
HMe AMB55 Me
Me HMe 0MB56
FIe Me HMe
0CR57Me Me HMe
CYM58 Me Me
HMe B2O33Me Me
HMe PMP60 Me
Me HMe BS Table 3
(continued) No, X Y Z
RB61 Me Et II
Me It62 Me
Et HMe Bz63 M
e Et HMe Ts64
Me Et HMe
Ms65 Me Et HM
e Phe66 Me Et
tl Me Prg67
Me Et HMe A
l168 Me Et HMe
Me69 Me Et
HMe AMB70 Me
Et II Me 0MB
71 Me Et It
Me 0CB72 Me
Et HMe CYM73 M
e Et HMe B2O3
3Me Et HMe PM
P75 Me Et HMe
B576 C1tl F
Me B77 CI HF
Me Bz78 Cj!
HF Me Ts79
CI HF Me Ms80
CI HF Me
Phe81 CI HCI M
e H82C1! , HC poor Me Bz
83 CI It CI
Me Ts84 Cf 1
1 CI2 shame, 85
C111CI! , Me Phe86
CI Me F Me
H87CI Me F
Me Bz88 Cf Me
F Me Ts89
CI Me F Me
Ms90 CI Me
F Me Phe Table 3 (continued)
) kX Y Z RQ91
Cf Me Cj! M
e B92 Cf2 Me
Cf Me Bz93
CI Me Cf2 Me
Ts94C2 CI Me
Ms95 CI Me
CI Me Phe96 C
I Et F Me
B97 Cj! EtF
Me Bz98 Cf2
Et F Me Ts9
9 CI Et F
Me Msloo CI Et
F Me Phelol
CI Et Cf Me
H102CI Et Cf2
Me Bz103 CI
Et CI Me Ts
104 CI Et Cf2
Me Ms105 CI
Et CI Me Phe1
06 Me HF Me
H107Me HF Me
Bz108 Me HF Me
Ts109 Me HF
Me Msllo Me H
F Me Hell Me
HCI Me H112Me
It CI Me
Bz113 Me HCf2
Me Ts114 Me HCI
Me Ms115 Me
It CI Me Ph
e116 Me Me F
Me tl117 Me M
e F Me Bz118
Me Me F FIe
Ts119 Me Me
F Me Ms120 Me
′! Ie F Me
Phe Table 3 (continued) No, X Y Z R port 121 Me Me CI
Me H122Me Me
CI Me Bz123 M
e Me (/! Me
Ts124 Me Me
CI Me Ms125 Me
Me Cf Me
Phe126 Me Et F
Me H127Me Et
F Me Bz128M
e Et F MeTs1
29 Me Et F
Me Ms130 Me Et
F Me Phe131
Me Et Cjl!
Me l1132 Me Et
CI Me Bz133
Me Et CI Me
Ts134 Me Et
CI Me Ms135 M
e Et CI Me
Phe136 CI HDr
Me +1137 CI HB
r Me Bz138 Cf
HI Shame H139C1tl
I Me 13z140
CI HEt Me
H141Cjl! HEt Me
Bz142 CI HMe
Me H143Cf2 HMe
Me Bz144 CI
Me Br Me H145
CI Me Br Me
Bzi46 Cf2 Me
I Met(147C4Me
I Me Bz148
CI Me Et Me
H149CI Me Et
Me Bz150 CI
Me Me Me It No.
3 Table (continued) No, X Y Z
R0151CI! , Me Me Me
Bz152 Ce Et
Br Me ) 1153 C
I Et Br Me
Bz154 CI Et I
Me H155CI Et
I Me Bz156
CI Et Et Me
H157C4Et Et M
e Bz158 CI Et
Me Me H159CI! ,
, Et Me Me
Bz160 Me HBr
Me I161 Me HBr
Me Bz162 Me
HI Me H163Me'
HI Me Bz164
Me HEt Me H16
5Me, HEt Me Bz
166 Me HMe Me
H167Me HMe Me
Bz168 Me Me
Br Me H169Me
Me Br Me Bz1
70 Me Me I
Me H171Me MeI
Me Bz172 Me Me
Et Me H173Me
Me Et Me
Bz174 Me Me Me
Me H175Me Me
Me Me Bz176
Me Ei Br Me
H177Me Et Br
Me Bz178 Me
Et I Me H17
9Me Et I Me
Bz180 Me Et
Et Me H Table 3 (continued) No, X Y Z
RQ181 Me Et E
t Me Bz182 Me
Et Me Me H
183Me Et Me M
e Bz184Cj2HF Et
H185CI HCI Et
lI186 CI Me
F Et HfB2 CI
Me CI Et
H188Cf Et F
Et 11189 Cj! E
t CI Et H190M
e HF Et H191
Me HCI Et lI1
92 Me Me F
Et l1196 Cj! I
t HPr(n) H197CI
II HPr(n) Bz19
8 CI HHPr(i) 111
99 C1it tl Pr
(i) Bz200 C11,Me
HPr(n) lI201 C4Me
HPr(n) Bz202 Cf2
Me tl Pr(i)
H2O3CI Me HPr(
i) Bz204 Cj! Et
HPr(n) H2O3C1Et
HPr(n) Bz206 CI! ,E
t HPr(i) H2O7CI
Et HPr(i) Bz208
Me HHPr(n) H2O9M
e I(HPr(n) Bz210
Me HIt Pr(i)
H Table 3 (continued) No, X Y Z
RQ211 Me HHPr(i)
Bz212 Me Me HP
r(n) H213Me Me
HPr(n) Bz214 Me
Me HPr(i) H215Me
Me HPr(i) Bz21
6 Me Et HPr(n)
H217Me Et HPr(
n) Bz218 Me Et
HPr(i) H219Me E
t HPr(i) Bz220 C
I C111Me H221Cf
C1HMe Bz222 C1(4
HMe Ta223 C1C1it
Me Ms224 CI
CI HMe Phe225 C
I Br HMe H226
CI Br HMe Bz2
27 CI Br tl
Me Ta228 CI B
r HMe Ms229 CI
Br If Me
Phe230 Cf2 F HM
e H231CI F H
Me Bz232 CI F
HMe Ta205 CI
F II Me Ms
234 CI F HMe
Phe235 Me Cf2
HMe II236 Me
CI HMe Bz237 Me
(4It Me Ta2
38 Me CI HMe
Ms239 Me CI H
Me Phe240 Me Br
HMe H Table 3 (continued) Na X Y Z R
Q241 Me Br II
Me Bz242 Me
Br HMe Ta243 Me
Br HMe Ms244
Me Br HMe
Phe245 Me F HMe
lI246 Me F
HMe Bz247 Me F
HMe Ta248 Me
F HMe Ms249
Me F HMe Phe2
50 CI C1l(Et H2
51CI Br If Et
H252Cj2F HEt
lI253 Me Cj! t
l Et lI254 Me
Br If Et l
I255 Me F II
Et H256Cf1Cj2 F
Me I257 Cf2
CI C4Me H258Cj
! Br F Me
H259CI Br Cf2
Me II260 CI F
F Me H261C1F
CI Me 11262
Me CI F Me
H263Me CI CI
Me H264Me Br
F Me H265Me
Br CI Me H
2O6Me F F Me
H267Me F CI
Me II268 Cf
T HMe H269Cf2
1 HMe Bz270 Cf2
Pr(n) HMe II No.
3 Table (continued) No, X Y Z
RQ300 Et HHrIe
Anb Table 3 (continued) No, X Y Z
RQ312 Pr(i) tl H
)1e Prg318 Pr(i)
It HMe CYM324
Et tl F Me
Ts330 Et HCj!
Me Me Table 3 (continued) No, X Y Z R mouth 360 EL Me C1! ,
Fle It Table 3 (continued) No, X Y Z
RQ390 Et F 11
Isao H Table 3 (continued) NCL X Y Z
RH391Et FIT
Me Bz392 Pr(i)
C1tl Me H393Pr(i
) CP! , HMe Bz394
Pr(i) Br HMe l
I395 Pr(i) Br tl
Me Bz396 Pr(i
) F HMe H397P
r(i) F HMe Bz
398 Et CI F
Me I399 Et C
I CI Me H400E
t CI Br Me
H420Pr(i) CI Et
Me H Table 3 (continued) No, X Y Z
RH421Pr(i) CI Me
MeI422 Pr(i)
Br F Me H42
3Pr(i) Br Cj!
Me I424 Pr(i) B
r Br Me H425P
r(i) Br I Me
lI426 Pr(i) Br
Et Me H427Pr(i)
Br Me Me
H428Pr(i) F F
Me H429Pr(i) F
Cf Me I430 Pr
(i) F Br Me
H431Pr(i) F I
Me H432Pr(i) F
Et Me H433Pr(i
) F Me Me
lI434 Et I HMe
H435Et I F
Me I436 Et
I Cf! Me H437
Et I Br Me
lI438 Et I
I Me H439Et I
Et Me H440E
t I Me Me
H44'l Et Pr(n)
HMe lI442 Et Pr
(n) F Me H443E
t Pr(n) Cj! Me
H444Et Pr(n)
Br Me I445 Et
Pr(n) I Me
H446Et Pr(n) Et
Me I447 Et
Pr(n) Me Me 11
448 Et Pr(i) HMe
H449Et Pr(i)
F Me H450Et P
r(i) Cj! Me Hth
3 Table (continued) NQ, X Y Z RH4
80Pr(n) HHMe Phe No.
3 Table (continued) Yang, X Y Z RH482
Bu(n) H'HMe Bz486
Br HHMe lI487
BrHHMe Bz488
Br HII Me Ts4
89 Br HHMe Ms49
0 Br HHMe Phe49
1 F HH addition H492F
HII Me Bz493
F HHMe Ts494FHH Order
4S 495 F HHMe Phe4
96 Pr(n) II F
Me H497Pr(n) It
CI Me I498
Pr(n) HBr Me
H499Pr(n) HE Me
lI500 Pr(n) HEt
Mell501 Pr(n)
HMe Me H3O2Bu(n)
tl F Me H
3O3Bu(n) HCfMe
H3O4Bu(n) HBr Me
lI505 Bu(n)
HI Me
lI506 Bu(n)
HEt Me H3O7Bu(n)
If Me Me
H3O8Br HF Me
H3O9Br HCl3 MeH51
0Br HBr Me If
Table 3 (continued) Na X Y Z R
H511Br HI Me
H512Br II Et
Mell513 Br HMe
Me H514F HF
Me I (515F tl
CI Me H516F
HBr Me H517FHI
Isao ll518 F H
Et Me H519F H
Me Mell520 Pr(
n) Me HMe H521
Pr(n) Me F Me
H522Pr(n)MeC
I Me H523Pr(n)
Et HMe H524Pr(n)
Et F Me l
l525 Pr(n) Et Cj
! Me H526Bu(n)
Me HMe H527Bu(n)
Me F Me l
l528 Bu(n) Me CI
Mell529 Bu(n)
Et HMe H530Bu
(n) Et F Me
H531nu(n) Et CI
Me H532Br Me
HMe H533Br Me
F Me H534Br
Me CI Me
H535Br Et HMe
H536Br Et F
Me 11537 Br Et
CI Me H538F
Me HMe ll539
F Me F Me
ll540 F Me CI
Me H Table 3 (continued) No;
H541F Et II M
e H542F Et F
Me H543F Et
CI! , Me H544Pr(n)
CI HMe H545Pr(n
) Br HMe H546P
r(n) F It Me
H547Pr(n) I HMe
H548Pr(n) Pr(n)
HMe H549Pr(n) Pr
(i) HMe H550Bu(n)
CI HMe H551Bu (
n) Br HMe H552
Bu(n) F HMe H5
53Bu(n) T HMe
8554 Bu(n) Pr(n)
HMe H555Bu(n) Pr(i
) II Me H556Br
CI HMe H557B
r Br It Me
ll558 Br F HM
e H559Br I HM
e H560Br Pr(n)
HMe H561Br Pr(i)
II Me H562F
C1HMe H563F Br
HMe H564F F
H shame 11565 F I
HMe H566F Pr
(n) HMe H567F
Pr(i) HMe ll5681
HHee H5691tl F
Mell570 1
HC4! Me H Table 3 (Continued)
) No, X Y Z
RH5711HBr Me H
572I It I
Me H573I HEt
Me H574 [HMe Me
H575T Me If
Mell576 I
Me P Me H57
7I Me CI Me
ll578 1 Me
Br Mell579 I
Me I Me
ll580 T Me Et
Me H5811Me Me
Me H5821Et H
Shame H5831Et FM
e ll584 r Et
C1Me H5851Et B
r Me 11586 I
Et I Me H
5871Et Et Me
ll588 1 Et Me
Me H589NO2HIt
Me H5QONOz HF
Me H591No2II
Cf Me H592NOz
HBr Me H593NOz
II I Me
11594 Not HEt M
e H595N02HMe Me
H596NOz Me HMe
H597NOz Me F
Me H598NOz
Me C4! Me H59
9NO2Me Br Me
ll600 NOz Me I
Me H Table 3 (continued) kX Y Z RH601N
Oz Me Et Me
11602 Not Me
Me Me H603NOx
Et HMe H604NOz
Et F Me H
605NOz Et CI2
Mell606 NO□Et
Br Me H607NOz
Et I Me H'6
08 NO2Et Et Shame
11609 NOz Et
Me Me H610CF3
H11 ship H611CF3 II
F Me H612CFz
HCj! Me H613CF
z HBr Me ll61
4 CFz II I
Me H615CF3 HEt
Mell616 CF:l
HMe Me H617CF:l
Me HMe ll61B
CF2 Me F Me
ll619 CF3 Me
C1Me H620CF, M
e Br Me H621C
Fz Me I Me
1t622 CF 3 Me
E t Me H623CF3
Me Me Me H
624CF3 Et HMe
1I625 CF x E t
F Me H626CF :l
E t CI Me
)1627 CF3 Et Br
Me H628CF3 E
t T Mell629
CF, Et Et Isao
ll630 CF 3 E t
Me Me It Table 3
(continued) No, X Y Z
RQ660 TFE Et HM
e H Table 3 (continued) No, X Y Z
RQ661 TFE CI! , HMe
ll662 TFE Br
HMe ll663 TFE F
HMe H664CI H
Pr(n) Mell665C
I HPr(n) Me Bz
666 CI2 It Pr(n
) Me Ts667 (1/!
HPr(n) Me Ms66
8 Cf HPr(n) Me
Phe669 CI HPr(i)
Mell670 CI2
HPr(i) Me Bz671
Cj! HPr(i) Me
Ts672 C1, HPr(i) Me
Ms673 CI HPr(i
) Me Phe674 (F!
tl Bu(n) Me
H675CI HBu(n) Me
Bz676 Cj! HBu(
n) Me Ts677 CI
HBu(n) Me Ms678
CI HBu(n) Me
Phe679 CI HBu(i)
Mell680 CI2
HBu(i) Me Bz681
CI HBu(i) Me
Ts682 CI HBu(i)
Me Ms683 CI HBu
(i) Me Phe684 CI
HBu(s) Me H68
5CI HBu(s) Me
Bz686 Cf HBu(s)
Me Ts687 CI2 HB
u(s) Me Ms688 CI
II Bu(s) Me
Phe689 CI HBu(t)
Me H690C4! HB
u(t) Me Bz Table 3 (Continued)
Nα XYZRQ 720 CI Me Bu(t)
Me Bz Table 3 (continued) No, X Y Z
R, 0721CI Me nu(
t) Me Ts722 CI
Me Bu(t) Me
Ms? 23 (4Me Bu(t)
Me Phe724 C4Et
Pr(n) Mell725
CI Et Pr(n) M
e Bz726 CI Et
Pr(n) Me Ts727
(4Et Pr(n) Me
Ms728 CI Et P
r(n) Me Phe729 C
I Et Pr(i) Me
1 (730CI Et Pr
(i) Me Bz731 CI
Et Pr(i) Me
Ts732 CI Et P
r(i) Me Ms733 CI
Et Pr(i) Me
Phe734 C1lEt Bu(
n) Me H735CI E
t Bu(n) Me Bz7
36 CI Et Bu(n)
Me Ts737 CE
Et Bu(n) Me Ms
738 C1, Et Bu(n)
Me Phe739 CI Et
Bu(i) Me H740
CI Et Bu(i) Me
Bz741 C1l Et
Bu(i) Me Ts742
CI Et Bu(i)
Me Ms743 CI Et
Bu(i) Me Phe74
4 CI Et Bu(s)
Me H745(4Et Bu(
s) Me Bz746 CI
Et Bu(s) Me
Ts747 CI Et Bu
(s) Me Ms748 CI2
Et Bu(s) Me
Phe749 CI2 Et
Bu(t) Mell750
CI2 Et Bu(t)
Me Bz Table 3 (continued) No, X Y Z
RQ751 Cl3 Et
Bu(t) Me Ta752
(4Et Bu(t) Me
Ms753 Cf Et Bu (
t) Me Phe754 Me
HPr(n) Me H755
Me II Pr(n) M
e Bz756 Me HPr(
n) Me Ta757 Me
If Pr(n) Me
Ms758 Me HPr(n)
Me Phe759 Me
HPr(i) Mell760
Me HPr(i) Me B
z761 Me HPr(i) M
e Ta762 Me HPr (
i) Me Ms763 Me
HPr(i) Me Phe76
4 Me HBu(n) Me
H765Me II Bu (
n) Me Bz766 Me
HBu(n) Me Ta767
Me) I Bu(n)
Me Ms768 Me H
Bu(n) FIe Phe769
Me HBu(i) Me
H770Me HBu(i) Me
Bz771 Me HBu(i)
Me Ta205 Me
HBu(i) Me Ms773
Me HBu(i) Me P
he774 Me HBu(s)
Me H775Me HBu(s)
Me Bz776 Me
HBu(s) Me Ta777
Me HBu(s) Me M
s778 Me HBu(s) M
e Phe779 Me HBu
(t) Me H780Me
HBu(t) Me BzTable 3
(continued) No, X Y Z RQ78
4 Me Me Pr(n)
Me H785Me Me
Pr(n) Me Bz789
Me Me Pr(i) M
e H790Me Me P
r(i) Me Bz791 Me
Me Pr(i) Me
Ta792 Me Me
Pr(i) Me Ms793 M
e Me Pr(i) Me
Phe796 Me Me
Bu(n) Me Ta797
Me Me Bu(n) M
e Ms798 Me Me
Bu(n) Me Phe799
Me Me Bu(i)
Me H800Me Me
Bu(i) Me Bz801
Me Me Bu(i) Me
Ta802 Me Me
Bu(i) Me Ms805
Me Me Bu(s) M
e Bz806 Me Me
Bu(s) Me Ta807
Me Me Bu(s)
Me Ms808 Me Me
Bu(s) Me Phe80
9 Me Me Bu(t)
Me ll810 Me M
e Bu(t) Me Bzth
3 Table (continued) No, X・Y Z RQ81
1 Me Me Bu(t)
Me Ta205 Me M
e Bu(t) Me Ms8
13 Me Me Bu(t)
Me Phe814 Me
Et Pr(n) Me H
815Me Et Pr(n)
Me Bz816 Me Et
Pr(n) Me Ta81
7 Me Et Pr(n)
Me Ms818 Me E
t Pr(n) Me Phe
819 Me Et Pr(i)
Me H820Me Et
Pr(i) Me Bz821
Me Et Pr(i)
Me Ta822 Me Et
Pr(i) Me Ms82
3 Me Et Pr(i)
Me Phe824 Me
Et Bu(n) Me H8
25Me Et Bu(n)
Me Bz830 Me Et
Bu(i) Me Bz831
Me Et Bu(i)
Me Ta205 Me Et
Bu(i) Me Ms83
8 Me Et Bu(s)
Me Phe839 Me
Et Bu(t) Me H8
40Me Et Bu(t)
Me Bz Table 3 (continued) NLIX Y Z RQ84
1 Me Et Bu(t)
Me Ta842 Me E
t Bu(t) Me Ms8
43 Me Et Bu(t)
Me Phe844 Cf
C1Pr(n) Mell845
Cf CI Pr(i)
Me H846 (/! Cl3
Bu(n) Me H847Cj!
CI Bu(i) Me
H848 (4C1, Bu(s) Me
H849' Cj! C.I.
Bu(t) Me H850CI
Br Pr(n) Me
H851CI Br Pr(i)
Mell852 C4Br
Bu(n) Mell853
Cf Br Bu(i) M
ell854 CI Br
Bu(s)Met(855C
I Br Bu(t) Me
ll856 C4! F
Pr(n) Me H857Cl3
F Pr(i) Me
)1858 CI F Bu(
n) Me H859 (4F
Bu(i) Mell860C
l3 F Bu(s) Me
H861CI F Bu(t
) Me H862Me C1
l Pr(n) Me H86
3Me CI Pr(i) M
e H864Me CI B
u(n) Me H865Me
(!!, Bu(i) Me H866
Me Cl3 Bu(s) M
e H867Me Cf B
u(t) Me H868Me
Br Pr(n) Me H
869Me Br Pr(i)
Me H870Me Br
Bu(n) Me ItTable 3
(continued) N (L X Y Z
RQ900 EtS Et HM
e II Table 3 (continued) No, X Y Z
RQ901 EtS Cj!
If Me ll902 E
tS Br II Me
! (903EtSF HM
e H2O2Pr(n)S HHMe
! (905Pr(n)S Me H
Me H2O2Pr(n)S Et
tl Me H2O2Pr(n
) S CI HMe ll908
Pr(n)SBr II M
e H2O2Pr(n)S F
HMell910 Pr(i)S
HHMe H911Pr(i)S Me
HMe H912Pr(i)S
Et HMe H913Pr(i)
SCI HMe H914Pr
(i) S Br HMe ll9
15 Pr(i)S F HMe
ll916 Ac HHMe
ll917 8c
Me tl
Me H918Ac
Et HMe H919Ac
Cj! HMell920
Ac Br
HMe ll9
21 Ac F HMe
H922MeOCtlz HHMe
H923MeOCHz Me It
Me H924MeOCHz E
t HMe H925MeOCtlz
(/! II Me
H926MeOCt(z Br HMe
H927MeOCH2F)I
Me H92811! tOc112
, HII addition ll929
EtOCTo Me tl M
e H930E tOcHz E t
II Me H Table 3
(continued) Na X Y Z R
Q960 Pr(n)Co II t
l Me H Table 3 (continued) Na X Y Z R
Q972 Bu(n)S HII M
ell978 Bu(S)SHH
-Me H979Bu(S)So HHM
e H2SOBu(S)SOz HHMe
H981Bu(t)S HHMe
H990Pr(+)OCHz II It
Isao II Table 3 (continued) No, X Y Z
RQ1107 (CH2)3H
Me H1108(CHz) x
HMe Bz1109-(C1h):+
-fl Me Tslllo
-(CHz)z HFle Ms
lllll -(CHz)z -HMe
Phe1112 - (C1,), -H wire
111113 (CH2) a
HMe Bz1114 (CH2
) a If Me Ts
1136 CI HHMe Me
Table 3 (Continued) N[lLX Y Z RQ [Left below] In Tables 1, 2 and 3, Me is a methyl group.
, Et is an ethyl group, Pr (n) is a normal propyl group
, Pr(i) is isopropyl group, Bu(n) is norm
rubyl group, Bu (i) is isobutyl group, Bu (s
) is a secondary butyl group, B'u(t) is a tertiary
-Butyl group, CLM is chloromethyl group, CLE is 2
-chloroethyl group, DFM is difluoromethyl group,
TFE has a 2,2.2-t-lifluoroethyl group, A
c is an acetyl group, B2 is a benzyl group, Ts is p-)
Ms is the enesulfonyl group, Ms is the methanesulfonyl group, P is
he is a phenacyl group, Prg is a propargyl group, A
ll is an allyl group, AMB is an α-methylbenzyl group, O
MB is orthomethylbenzyl group, OCB is orthochloro
Rubenzyl group, CYM is cyanomethyl group, 8zO is
benzoyl group, PMP is paramethylphenacyl group,
BS each represents a Hensensulfonyl group.

Among the compounds in Tables 1 to 3, compounds in which Q is a hydrogen atom easily form salts with metals or organic bases.

Metals include sodium, potassium, calcium, barium, lithium, magnesium, iron, and Fi.

Manganese and nickel are mentioned, and the bases include methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, n-propylamine, di-n-propylamine, isopropylamine, diisopropylamine, n-butylamine, isobutylamine, secondary Examples include butylamine, tert-butylamine, pyridine, and choline. Furthermore, ammonia can be mentioned as another base.

Regarding the compounds in Tables 1 to 3 in which Q is a hydrogen atom, these 27 types of salts are also included.

Next, Table 4 shows the melting points of these compounds.

Table 4 Compound Numbers Melting Points (C) 'H-NMR of these compounds are shown in Table 5.

Table 5 Compound number Nl l)l-NMR (δ, ppm)
(Solvent) In the compound number 1t in Tables 4 and 5, "1-" indicates the compound in Table 1, "2-" indicates the compound in Table 2, "3-" indicates the compound in Table 2, and "2-" indicates the compound in Table 2. -” indicates the third
It means the compound in the table, for example rl-2J represents the compound 1lh2 in Table 1.

Hereinafter, compounds will be represented according to this standard.

When the compound of the present invention is applied as a herbicide, it is generally carried out using a suitable carrier, such as a solid carrier such as clay, talc, bentonite, diatomaceous earth, or water or an alcohol (methanol, ethanol, etc.).

Aromatic hydrocarbons (benzene, toluene, xylene, etc.)
, ethers, ketones, esters (ethyl acetates, etc.), acid amides (dimethylformamide, etc.), and can be applied in combination with a liquid carrier such as a surfactant, a dispersant, a suspending agent, etc., if desired. , adding penetrants, spreading agents, stabilizers, etc., emulsions.

It can be put to practical use in any dosage form such as a wettable powder or a single powder.

In addition, other types of herbicides may be used during formulation or spraying as necessary [e.g., Farm Chemical Handbook, (1)
984)], various insecticides, fungicides,
It may also be used in combination with a synergist.

Next, specific formulation examples of formulations using the compounds of the present invention will be shown. Parts indicate weight. However, the formulation examples of the present invention are not limited to these only.

Sarakin Goto Wettable powder Compound of the present invention 1kl-292...60 parts Sieglite PFP...33 parts (Kaolin clay: Sieglite Kogyo ■Product name) Tsurupol 5039... ...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical's product name) Carplex (anti-caking agent) ...2 parts (white carbon: Shionogi M Drug ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.

■Five main components of light Wettable powder Compounds of the present invention Magnetic 1-1...60 parts Sieglite PFP...33 parts (Kaolin clay: Sieglite Kogyo ■Product name) Tsurupol 5039 Old...・5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (anti-caking agent) 2 parts (white carbon: Shionogi & Co., Ltd. ■ Product name) Mix and grind the above ingredients uniformly to make a wettable powder.

ΣΔL Example" - Hydrating agent Compound of the present invention ml - 46...60 parts Siegrite PPP...33 parts (Kaolin clay: Sieglite Kogyo ■trade name) Tsurupol 5039... ...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■trade name) Carplex (anti-caking agent) ...2 parts (white carbon: Shionogi & Co., Ltd.) ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.

Formulation example 4 Wettable powder Compound of the present invention i'h 1-245 ...--6
Part 0 Sieglite PFP ・・・・・・33
part (kaolin clay: Sieglite Kogyo brand name) Tsurupol 5039...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical CMJ brand name) Carplex (solid) Anti-caking agent) 2 parts (white carbon: Shionogi Co., Ltd.'s drug brand name) or more are uniformly mixed and pulverized to make a wettable powder.

Plate plate Wettable powder Compound of the present invention N[L346...60 parts Sieglite PFP...33 parts (
Kaolin clay: Zeeklite Kogyo ■Product name) Tsurupol 5039 ... 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (caking prevention 2 parts (white carbon: Shionogi & Co., Ltd. trade name) or more are uniformly mixed and pulverized to make a wettable powder.

Emulsion Compound of the Invention k3-307...Archie, 5-part xylene...
...7 8.5 parts dimethylformamide ・
... 15th part Tsurupol 2680 ...
...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical's trade name) The above is mixed uniformly to form an emulsion.

Example n] - Emulsion Compound of the present invention ¥yJ N13-46 ・・・・・・1
．． Part 5
...7 8.5 parts dimethylformamide
・・・・・・15 part vine pole 2680
...5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■ trade name) The above is mixed uniformly to form an emulsion.

Formulation Example 8 Flowable Compound of the Invention Patient 3-292 40 parts Agelisil B-710 10 parts (nonionic surfactant: Kao brand name) Lunonox xoooc
...0.5 part (anionic surfactant:
Toho Chemical ■Product name) 1% Rhodopol water...
...20 parts (thickener: Lone Boulin product name)
water ·····
・Mix 29.5 parts or more uniformly to make a flowable agent.

Father Bean Five Masters Flowable Inventive Compound! ml-46...40 parts Agelisil B-710...10 parts (nonionic surfactant: Kao brand name) Runofux 100OC...
...0.5 parts (anionic surfactant: Toho Chemical ■trade name) 1% Rhodopol water ...20 parts (thickener: Lone-Boulin trade name) water
... 29.5 parts or more are mixed uniformly to form a flowable agent.

■ Bean History Flowable Compound of the Invention N[Ll-31...40 parts Agelisil B-710...10 parts (Nonionic surfactant: Kao ■Product name) Runofukus 100OC...・
...0.5 part (anionic surfactant: Toho Chemical ■trade name) 1% Rhodobol water ...20
Part (thickener: Cohn-Boulin product name) water
... 29.5 parts or more are mixed uniformly to form a flowable agent.

Sawaoka Gototo Granules Compound of the present invention NIL-47...1.0 parts Bentonite...55.0 parts Tarri...4
At least 4.0 parts are uniformly mixed and pulverized, then a small amount of water is added, stirred and kneaded, granulated using an extrusion granulator, and dried to form granules.

Municipal plate builder Liquid agent Compound of the present invention Soda salt of Kan 1-1...30 parts Nifpol...10 parts (Nonionic surfactant: Nissan Chemical ■trade name) Water
... 60 parts or more are mixed uniformly to form a liquid agent.

Tsurupol W-150...10 parts (nonionic surfactant: Toho Chemical ■trade name) water
... 80 parts or more are mixed uniformly to form a liquid agent.

When using, the above-mentioned hydrating powders, emulsions, flowable preparations, and liquid preparations should be diluted 50 to 1000 times with water to ensure that the active ingredients are lha
Spray at a ratio of 0.01 to 10 kg per person.

In addition, the compound of the present invention can be applied to control various weeds in non-agricultural lands such as playgrounds, open spaces, and railroad tracks, in addition to agricultural and horticultural fields such as fields, paddy fields, and orchards, and the amount of application depends on the application situation. There are differences depending on the application period, target grass species, cultivated crops, etc., but in general it is 0.01 per hectare (ha).
A ratio of about 10 kg is appropriate.

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

30cm test line for weeding effect by soil treatment
, Put sterilized diluvial soil in a plastic box measuring 22 cm wide and 60 cm deep, and grow Japanese barnyard grass, foxtail grass, red grass, bluetail, Japanese knotweed, and Japanese crocodile.

Sow yellow sedge, turgid, and wheat, and about 1.
After covering the soil for 5 am, the active ingredient was uniformly spread over the soil surface so that the amount of the active ingredient was at a predetermined ratio. The chemical solution used for spraying was the wettable powder, emulsion or flowable powder of the formulation example described above diluted with water and sprayed over the entire surface with a small sprayer. Three weeks after spraying the chemical solution, the herbicidal effect on various weeds was investigated according to the following criteria.

Judgment Criterion 5: Weed killing rate of 90% or more (almost complete death) 4...
・Weed killing rate 70-90% 3... Weed killing rate 40-70% 2... Weed killing rate 20-40% ■... Weed killing rate 5-20% 0... Weed killing rate 5% or less (Haton) However, the above-mentioned herbicidal 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.

In addition, phytotoxicity to various crops was investigated according to the following criteria. The results are shown in Table 6.

Criterion 5: The crop is almost completely dead 4: The phytotoxicity of the crop is significant 3: The phytotoxicity of the crop is observed 2: Some phytotoxicity of the crop is observed 1: There is almost no phytotoxicity of the crop Not observed at all 0... No chemical damage to crops is observed by Yuji Fuguchi Test box 3 for herbicidal effect by treatment of seedlings
0a11. Fill a plastic box with a width of 22cm and a depth of 6CI11 with sterilized diluvial soil, and store barnyard grass, foxtail grass,
Kingfisher, blueberry, Japanese knotweed, and Japanese crocodile.

Seeds of yellow muscaria, trumpet gum, and wheat were sown in spots, and the soil was covered with about 1.5 coats of soil.

When each plant reached the 2-3 leaf stage, the supplement was uniformly sprayed on the seedlings at a predetermined ratio.

The chemical solution used for spraying was the wettable powder, emulsion, or flowable powder of the formulation example described above, diluted with water, and sprayed over the entire surface of seedlings of various weeds and crops using a small sprayer.

Four weeks after spraying the chemical solution, the herbicidal effects on various weeds and the chemical damage to various crops were investigated according to the criteria of Test Example-1. The results are shown in Table 7.

The structural formulas of the control compounds in Tables 6 and 7 are as follows.

(-Ship name Virazolate) (Compound described in JP-A-58-185568) C
H.

(Compound synthesized according to Examples) Control compound D: CH2

Claims (7)

[Claims] (1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼Pyrazole derivative represented by (I). [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. Q is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom, a lower alkenyl group optionally substituted with a halogen atom, a lower alkynyl group optionally substituted with a halogen atom, a cyanomethyl group, the following formula; , chemical formulas, tables, etc. ▼ group (in the formula, A represents a hydrogen atom or a lower alkyl group,
m represents 0 or 1. B represents a phenyl group or a lower alkyl group which may be substituted with up to four same or different substituents selected from a lower alkyl group, a halogen atom, a nitro group, and a trifluoromethyl group. ) or represents an organic acid residue. ]. (2) General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) A salt of a pyrazole derivative represented by the following with a metal or organic base. [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. ]. (3) The following formula (III): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ 1-methyl-5-hydroxypyrazole represented by (III) and the general formula (IV): ▲ There are mathematical formulas, chemical formulas, tables, etc. General formula (II) characterized by reacting with the compound represented by ▼(IV): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) A method for producing the compound represented by. [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. M represents a hydroxyl group or a halogen atom. ]. (4) General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Reacting the compound represented by (II) with the compound represented by general formula (V): L-Q(V) General formula (I) characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼A method for producing a pyrazole derivative represented by (I). [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. Q is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom, a lower alkenyl group optionally substituted with a halogen atom, a lower alkynyl group optionally substituted with a halogen atom, a cyanomethyl group, the following formula; , chemical formulas, tables, etc. ▼ group (in the formula, A represents a hydrogen atom or a lower alkyl group, m
represents 0 or 1. B represents a phenyl group or a lower alkyl group which may be substituted with up to four same or different substituents selected from a lower alkyl group, a halogen atom, a nitro group, and a trifluoromethyl group. ) or an organic acid residue, and L represents a halogen atom, a methanesulfonyloxy group, or a para-toluenesulfonyloxy group. ]. (5) General formula (VI): ▲There are mathematical formulas, chemical formulas, tables, etc.▼General formula (I) characterized by reacting the compound represented by (VI) with an oxidizing agent: ▲Mathematical formulas, chemical formulas, tables, etc. etc. ▼(I) A method for producing the compound represented by. [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 1 or 2. Q is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom, a lower alkenyl group optionally substituted with a halogen atom, a lower alkynyl group optionally substituted with a halogen atom, a cyanomethyl group, the following formula; ▲Math. , chemical formulas, tables, etc. ▼ group (in the formula, A represents a hydrogen atom or a lower alkyl group, m
represents 0 or 1. B represents a phenyl group or a lower alkyl group which may be substituted with up to four same or different substituents selected from a lower alkyl group, a halogen atom, a nitro group, and a trifluoromethyl group. ) or represents an organic acid residue. ]. (6) General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ By reacting the compound represented by (II) with a chlorinating agent, general formula (VII): ▲Mathematical formulas, chemical formulas, tables, etc. After leading to the compound represented by ▼(VII), this compound (VII) is reacted with the compound represented by the general formula (VIII): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(VIII) General formula (I) characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼Method for producing the compound represented by (I). [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. Q is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom, a lower alkenyl group optionally substituted with a halogen atom, a lower alkynyl group optionally substituted with a halogen atom, a cyanomethyl group, the following formula; , chemical formulas, tables, etc. ▼ group (in the formula, A represents a hydrogen atom or a lower alkyl group, m
represents 0 or 1. B represents a phenyl group or a lower alkyl group which may be substituted with up to four same or different substituents selected from a lower alkyl group, a halogen atom, a nitro group, and a trifluoromethyl group. )
Or represents an organic acid residue. ]. (7) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼Compounds represented by (I) or general formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) 1. A selective herbicide comprising, as an active ingredient, one or more salts of compounds with metals or organic bases. [In the above formula, X represents a lower alkyl group, a halogen atom, a lower haloalkyl group, or a nitro group, Y represents a hydrogen atom, a lower alkyl group, or a halogen atom, and Z is
Represents a hydrogen atom, lower alkyl group or halogen atom,
R represents a lower alkyl group, and n represents an integer of 0 to 2. Q is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom, a lower alkenyl group optionally substituted with a halogen atom, a lower alkynyl group optionally substituted with a halogen atom, a cyanomethyl group, the following formula; , chemical formulas, tables, etc. ▼ group (in the formula, A represents a hydrogen atom or a lower alkyl group, m
represents 0 or 1. B represents a phenyl group or a lower alkyl group which may be substituted with up to four same or different substituents selected from a lower alkyl group, a halogen atom, a nitro group, and a trifluoromethyl group. )
Or represents an organic acid residue. ].