CA1188697A - Phenoxyalkylamide derivative, process for preparing the same, herbicidal composition containing the same and method for controlling weeds by the use of the same - Google Patents

Phenoxyalkylamide derivative, process for preparing the same, herbicidal composition containing the same and method for controlling weeds by the use of the same

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Publication number
CA1188697A
CA1188697A CA000413389A CA413389A CA1188697A CA 1188697 A CA1188697 A CA 1188697A CA 000413389 A CA000413389 A CA 000413389A CA 413389 A CA413389 A CA 413389A CA 1188697 A CA1188697 A CA 1188697A
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Prior art keywords
group
butyramide
chloro
hydrogen atom
benzyl
Prior art date
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Expired
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CA000413389A
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French (fr)
Inventor
Tetsuo Takematsu
Yasutomo Takeuchi
Mitsuaki Takenaka
Seiji Takamura
Minoru Nishimura
Tatsuo Okada
Yasuhisa Fukuda
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Ube Corp
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Ube Industries Ltd
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Priority claimed from JP16634381A external-priority patent/JPS5867653A/en
Priority claimed from JP20994681A external-priority patent/JPS58113156A/en
Priority claimed from JP20994581A external-priority patent/JPS58113155A/en
Application filed by Ube Industries Ltd filed Critical Ube Industries Ltd
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Publication of CA1188697A publication Critical patent/CA1188697A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Abstract:

There are disclosed a novel phenoxyalkylamide derivative represented by the formula

Description

Phenoxyalkylamide derivative, process for preparing the same, herbicidal composition containing the same and method for controlling weeds b~ the use of the same This invention relates to a novel phenoxyalkylamide (phenoxyalkanoic acid amide) derivative, a process for preparing the same, a herbicidal composition containing the same as an active ingredient and a method for con-trolling weeds by the use of the same as a herbicide.
More particularly, this invention relates to a novel phenoxyalkylamide derivative represented by the formula (I):

~n ~ O-CHCON ~ (I) y CH~Z

wherein X: a lower-alkyl group, a lower-alkoxy group, a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;

il6~

Z: a phenyl group, a substituted phenyl group represented by the following formula S ~ R
m (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom;
and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group, or a furyl group;

R : a lower-alkyl group;

R2- a hydrogen atom, a lower-alkyl group, a lower-alkenyl group~ a lower alkynyl group or a lower-alkoxy group; and R : a hydrogen atom or a lower-alkyl group, a process for preparing the same, a herbicidal composition containing the same as an active ingredient, and a method for controlling weeds by the use of the same as a herbicide.
In accordance with the present invention there is thus provided a process for preparing a phenoxyalkylamide derivative represented by the formula - 2a -X ~ O-C~CON
~ -~ \
y CH-Z

wherein X: a lower-alkyl group, a lower-alkoxy group a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;
a phenyl group, a substituted phenyl group represented by the following formula m (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom; and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group or a furyl group;
Rl: a lower-alkyl group, ~-R2: a hydrogen atom, a lower-alkyl group, a lower-alkenyl ~roup, a lower-alkynyl group or a lower-alkoxy group; and ,~ ~
~1 .,, - 2b -R3: a hydrogen atom or a lower-alkyl group, which comprises reacting a compound represented by the formula Xn ~ O-L
y /~/

Rl wherein L represents a group of -CHCO-A or a hydrogen atom;
(in which A represents a chlorine atome or a bromine atom; and Rl has the same meaning as defined above), and X, n and Y have the same meanings as defined above, with a compound represented by the formula / R
M-N~
CH-Z

wherein M represents a hydrogen atom or a group IRl of A-CHCO-;
(in which A and Rl have the same meanings as defined above), and Z, R2 and R3 have the same meanings as defined above, IRl provided that when L is -CHCO-A, M is a hydrogen atom and IRl when L is a hydrogen atom, M is A-CHCO-, in a solvent in the presence of a base.

.

- 2c -The present invention also provides a method for controlling weeds which comprises applying to such weeds an effective amount of a phenoxyalkylamide compound as defined above~
In this specification, the term <~lower means to have 1 to 4 carbon atoms. For example, lower-alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and the like.
There have long been proposed a large number of herbicidal compositions containing phenoxy series compounds /

.

as ac-tive ingredients, not a small number of which have been commercially available. Such compounds include, for example, 2,4-D (active ingredient : 2,~-chloro-phenoxyacetic acid), 2,4-DP (active ingredient : 2-(2,~-dichlorophenoxy)propionic acid), MCP (active in~reclient : 2-methyl-~-ch]orophenoxyacetic acid), and MCPCA (active ingredient : N-(2-chlorophenoxy)-2-methyl-~-chlorophenoxyacetamide). In general, these phenoxy series herbicidal compositions known to the art have extremely prominent herbicidal effects against a wide variety of broad leaved weeds as compared with other herbicidal compositions. However, they have common problems that the effect is accompanied by phytotoxi-city against rice crops such as tiller depression and induction of monstrosity due to the auxin action.

It is, accordingly, a primary object of this invention - to provide a novel phenoxyalkylamide derivative of the above formula (I) which shows an excellent herbicidal effect and does not exhibit any phytotoxicity against crops.

Another object of this invention is to provide a process for preparing the above-mentioned phenoxy-alkylamide derivative of formula (I).

A further object of this invention is to provide a herbicidal composition which comprises as an active ingredient at least one of the phenoxyalkylamide derivative of formula (I).

A still further object of this invention is to provide a method of use of the above-mentioned phenoxyalkyl-amide derivative of formula (I) as a herbicide.

The present inventors have synthesized various kinds of phenoxy series compounds and investigated their herbi-cidal activities. As a result, they have succeeded in synthesizing a new group of the phenoxyalkylamide derivative of formula (I) which has never been des-S cribed in literatures, and also found that such newphenoxyalkylamide derivative can show a remarkable herbicidal effect against various weeds generated in a paddy field, a plowed field, an other cultivated and non-cultivated fields, without any phytotoxicity to crops, and have an ability to herbicide weeds selec-tively~ This invention has been, therefore, completed upon these findings.

According to one aspect of this invention, there is provided a new group of the phenoxyalkylamide derivative of the above formula (I). Representative example of the phenoxyalkylamide derivative (I) is given in Table l shown hereinbelow for illustrating purpose only.

In view of the herbicidal effect, preferable is an phenoxyalkylamide derivative represented by the fol].ow-ing formula (II):
1' R
X n ~ O-C~CON~
Y ~ 2 wherein X': a methyl group or a chlorine atom;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, X's may be the same or different;
Y': a hydrogen atom or a trifluoromethyl group;
Z': a phenyl group, a 2-methylphenyl group, a 2-chlorophenyl group, a thienyl group, a 2~pyridyl group or a 3-pyridyl group;
R : an ethyl group or an n-propyl group; and R : a hydrogen atom or a methyl group.

As particularly preferable compounds may be mentioned the Eollowing compounds.

CQ¢~ oCHCoNHCH2~;3 N Benzyl-2-(4-chloro-3-methylphenoxy)-butyramide CQ~-ocHCoN<CH3_~ 3 N-Benzyl-N-methyl-2-(4-chloro-3-methylphenoxy)-butyramide CQ ~ OCHCONHCH2 /
~H3 N-Benzyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide C~ ~-01 3co~3_~

N-Benzyl-N-methyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide ~H3 C2H5 CQ ~ -OCHCONHCH

N-(2-Methylbenzyl)-2-t4-chloro-3,5-dimethylphenoxy)-butyramide CQ ~ 12 5 ~

N-Benzyl-2-(3,4-dichlorophenoxy)-butyramide CQ~OCHCONHCH2~

N-Benzyl-2-(3,4-dichlorophenoxy)-valeramide ~3-oCHCoNHCH2~

N-t2-Pyridylmethyl~-2-(3,5-dimethylphenoxy)-butyramide C2H5 ~3 N-Thienylmethyl-2-(4--chloro-3 methylphenoxy)-butyramide C Q ~- OCHCONHCH 2 ~,3 N-Thienylmethyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide ~1 C 2 H 5 N-(2-Pyridylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-(3-Pyridylmethyl)-2-(4-chloro 3,5-dimethylphenoxy)-butyramide ~ OCHCONHCH2 ~

N-Benzyl-2-(3-trifluoromethylphenoxy)-butyramide OCHCONHCH

N-(2-Chlorobenzyl)-2-(3-trifluoromethylphenoxy)-butyramide ~ OCHC ONHCH 1,~3 N-Thienylmethyl~2-(3-trifluoromethylphenoxy)-butyramide CQ~oCHCONHCH2~3 N-Ben3yl-2-(4-chloro-3-trifluorometilylphenoxy)-butyramide CQ ~ OCHCON < 3 ~

N-Benzyl-N-methyl-2-(4-chloro-3-trifluoromethyl-phenoxy)-butyramide C~-OC'.COU~H ~

N-(3-Pyridylmethyl)-2-(4-chloro-3-trifluoromethyl-phenoxy)-butyramide In the following Table 1, there will be exemplified phenoxyalkylamide derivatives according to the present invention.

In the following Table 1, the values on the upper and S lower lines in the column of Elementary analysis for each compound are calculated and found values, respectively.

Table . . _ Com- Physico- Elementary pouncl Chemical formula chemlcal an ~ ysls No. properties H C ¦ N
_ _ ~ l C2 Hs ~ I ~lO 75.81 sæo 1 ~--o C~CONE!C~ m.p.55~5~C
~ - \=~ 7~ 76.00 sæs -C2~ C~3 I I 7A2'7 76æg 4~34
2 ~ OCE[CONH C~ ~ > ~. 73--76 C
~ ~ 7.50 76.a0 S OO
_ _. .
C2 ~
I C 3 7~ 76.29 g.94
3 ~ -O CYCON< ~ 1.5S20 C~2--~ 7.9~0 76.00 a.c~O

C~ 5 I
7.a7 -7629 4.9 67~o C~ CONE!C~ ~ m.p.82~84C
É - 7.60 75.57 ~7 ~ 3 C,~ ~ ' _ _I
7A27 76.29 ~ T
S ~ -~ C~CONECE~ -~ ~.~.5v~57c CH3 75 1 ~6.02 ~~ .91 C~-5 _ I r \ 7.~7 ~.29 ~L.gg 6 ~ CXC Ol`~Y~-2~\,~C TL:L I ;~L.?.89~90C
7.6~ 765 ¦ .L 9L i _ __ , ____ _ ~ _ Table 1 (cont'~) . _ ~ . .. . _ __ 7 ~30 CEICON~C~2~ m.p.75~77C 7.07 72~1 4.6~
C H 3 7.22 7236 ~63 C2~ _ 8 ~ O C E C O Nl~l C ~ 2 ~ m.p . 55 ~57 C 7.07 '7221 4.68 __ `OCH3 7~27 72.46 4.64 . C2~-!S , _ 9 ~ O C ~I C O ~ ~ C ~ z ~==~ OaE 3 ~Lp . ~30 ~ 82 C 7.û7 72.21 ~68 7.34 71.95 4.4 a2 ~ .
~-o ~ ;~ C O~i C~I2 ~ m p . 66 ~68 CS ~7 ~7.21 4~61 - C~ 6.00 ~)737 ~L.58 ~r~ O C~lcoNT C æ~3V~! m.p.87~8~'C 5.97 6'7~1 ~L.61 ~?Ei5 6.~l~ oo.g5 4.60 12 ~ PCON-T~ 2~) m.p.ol~o.~C 7 ~L7 7O ~g 7.47 7~2 ~9 Table 1 (cont'd) Oy~ __ _ l 7.80 76.7~ ~71 13 ~--O CPC0NHCH2 ~-CPl 3Lp.75~7r7C
~=~C~3 7~2 75.84 4.92 a 2 H s l 7.40 72.82 4.47 1 4 ~o CPCONPCP Z ~ O CX3 ~p .68 ~70 C
CH3 7.49 7~69 ~L.70 C~ ~5 6.3g 68~2 ~a~
1 5 ~OCHC0NHC~C~ m.p.69~71C
~=~ C~3 6.4~ 68~9 ~.43 ~2 Ys I 77a 7O,~g ~, lo ~O CHCONHC-~z~ m.p.66~ô8C
~ 7.44 75.50 51 C2~5 - -I 7~0 7~.73 ~71 17 ~ ~CON~CP~ ~- C~3 ~,p.~9~~1C
~Y~ 7~1 r~6.r/5 ~.~3 - C~ ~15 _ _ _ 18 (/~O C~C01N~C~7 ~O C~3 ~L~ .5v 57 C rt 40 rt~23 1~.47 I _ ~ ~ __ ~ 4v t2 6L 4~

Table 1 (cont' d) __ _ _ . ._ _ I m 2~ 7~7 76.2 ¦d,94 19 CE~3 ~-ocElr~oNP-cE~2 ~ 70~
~1C 7.80 ~6.5 15~3 ~2 ~
I m.p. 7.80 76.73 4.71 2 0 CH9 ~3 C~CCNE~CH2 ~ ~3 8 1~ , 83~C 7.85 76.30 4.80 _ C2 ~I5 l ~ m.p. 7.~0 72.~2 ~47 2 1CEI3 ~OCHCON~lC~72 ~--OC~3 8 5~
87C 7.20 7311 ~56 _ C2 ~
I m~?- o.34 68.0Z ~Ll 2 2 C~I3 ~-OCE~Co~~ a~ 6 5~
67C 6.57 68.20 ~ 30 ~"~15 _ m p . 7.80 76.73 4.71 23 ~--OC~CONELCEI~ ~3 102~
~CH ` - 104 C 7~7 70.S~ ~L.67 CEl3 3 C,~, l - C ~~ 3 ~) .p. 8.09 ~7.13 4.50 2 4 ~9--OCHCOh- / 172~175 c~3YC~3 CF~ ~ L~ 8.2C 772C ~oS

Table 1 (cont'd) .. , . . _._ .,._ .
C~ H3 CEI3 ~ I >~ m.~. 8.0Q 7713 ~iO
~/~OCHCONHOH2 ~ 98~
_ GH3 CH3 9 9 C 819 77 03 4~lL7 C2 E5 CH 3 Q~ m.p. 7.70 73.36 4,28 26 ~OaElCONHC~2 ~ 68~
CH3 CH3 7 0 C 7.82 73.32 4 __ C7 E~s _ ~ I ~ m ~. 7.80 76.73 4.71 27 CHs~/ ~OCHCONHO~2 ~ 78~
G'H3 7 9 C 8.02 77.27 4.76 C~, ~15 ~H .
~I ,~ 3 ~?- 8.~9 7713 4.50 28 CH3 ~~ OCHCONHCEI2 ~ 73~
CH3 7 6cc 8.25 7710 d,54 . . _ _ C2 ~5 CH 3 ~ I ~ m.p.7.7U 7336 4.28 2 9 C~ ~i ) C ~I C ON~ C ~ ~ 91 ~
~, _ 9 2C7.80 73.4~ ~L~30 . CE 3 CH G 2 ~ 5 _ _ ~ I ~ m.p.7~!30 76.73 A.71 3 0 ~ O C E~C ONP CE,, ~) 9 3--CH3 9 ~C 79~1 76.91 ~.71 Table 1 (cont'd) ~ _ _ _ _ C~, Cl 2a5 CH n2D 8.0gl 7.1 1450 31 ~--o a a c o N / ~3 1. 5 ~ 9 1 8.36 77.7~ i45B

C\H3 IC~ C~ Tn,P 8.09 71 14.so 32 ~ocHcoNHc~2 ~ 114--C>=' 116C 8.~1 7.09 4~S

CH3 I C2 H~ C p-3 m.~ . 8 0g 7715 4.50 3 3 ~ 0 C H C ON~ C a. ~ 8 0 ~
~ 82C 7.88 6.9a~ g.63 ~ 3 .
H3 C7 El!5 _ ~ ,~ ~.p. 8.09 713 g.50 3~L ~-OCaa ONa9P2 @~ C~ 112~
_ CH3 113~ 8.30 7~7 4.47 ~ES C~ ~5 CH30~ m.~. 770 73~6 4~8 ~OCHCONHC~ ~ 82~ .
C~ 8 4C 792 74.~2 '1 ~5 0~3 C-Hs OCH3 m.p. 770 73.36 ~28 36 @3--oC~lCPN~CE2 ~ 103~ .
~ . 1 0 5~C 7.51 73.o6 9~7 1~_ OE~3 . .

Ta~le 1 (cont ' d) ~ _ _ _ I C~3 C~ Hs m.p. 7'7 1~3~o ~28 3r, ~7~oCE~C ON~Ca2 -~oca3 82~
C~ ~C 8.06 73.59 41 _ C~ c2 ~5 C-9 m.p. 6.o8 68.77 4~2 38 ~oc~coN~c~2 ~ 93~
~ 95C 6.99 69.00 ~ 2 . ~3 _ CH~ Cl 2 Es CH~ - C~ = CH2 n~5~ 7.0 ¦ 71.05 ~77 39 ~OCECON/ ~5~2 C~2 ~ 7.40 70.83 3~86 CH3 C~
CH3 C2 Hs m.p.
I 100~~ô8 6877 ~2 40 ~OCHCONHC~ ~CQ 102 C . _ ~_, 692 68.91 451 C~-3 . - l ~3 C 3 E7 - ~ m ~. ~09 77.15 ~SO
4 1 ~0 C~ C O N~ C ~2 - ~ ~ 7 '~
_W \=~ _ ~ 7~ 76.70 ~57 C2 ~s m.pO730 7673 4~1 2 C~3 ~OC~CO~CY~ ~ 80~ . . _ CE3 83 C 781 ~716 4~72 Table 1 (cont'd) _ _ _ _ __ _ ___ !
. Cz E~s CH 97_~ m.p. 7~70 73.36 ~L28 43 CH3--~OCE~CONHCE[z ~/ \~ 89~
C}13 9 0 ac 7,r~5 72.86 ~26 _ C2E[5 ._ _ I m.p.8~)9 7715 4.53 44 CE[3 ~OCECONHa~2 ~C~3 80~
C~391C 810 7655 4.53 - CzE~3 _ _ I_ . I~. ô.68 68.~t7 ~a22 g5 CH3~--ûC~lCON~lCH~ ~a~ 63~
CE~365C 6.76 69.03 4~24 Im.p. 6.34 68.02 'L.41 4 6C ~--S~OC H CONPCE!~ ~3 98~
---\C~139 9 C ô.~1O 68.05 4~0 C~~
.m ~. 634 68.02 47 CE1~ OCHCON~lC~12~ 93~
Cl ~ SC o.~7 681Z ~L~g .
C2 ~5 C~7 I ~m.~. 6.68 ~.7'7 ;,~z :
~3 CE3 ~O CELC O~-HCH~ \) 9 9~
C'~ 1Ol~C 6.73 6~.14 ~16 .

Table 1 (cont'd) . _ Ct2 H5 m-P^6~ 68.02 41g 4 9 C~ ~ o C H C ON~ a H2 ~ 9 5 ~ I
~d 9 7C 6.~2 68.4- ~19 _ O E3 __ Cz ~ ~25 6 6~8 68.77 4æ2 CQ~3--OCHCON~
,~ \ C H ~ L 5 5 ~ 9 7.05 6326 3.86 C ~ H5 H 3 _ t C~ m ~.6.68 68.77 4~22 51 CQ4 3--OCElCONHOHz ~115~
,~=,117 C 6.88 68.48 3.96 . C ~ !
o~ H~ CH3m.p. 6 68 68.77 4.22
5 2 CQ~/~O C ElC ONECE~2 ~ 8 8 ~ . i Y 9 0 C 6.89 o8.89 4.10 CE~3 _ I m.~. 6.68 68.77 ~22 ;
5 3 C ~--~q~ O C H C O N E~ C ~2 ~E3 113 ~ _ >=~ 11 5C 7.00 6~48 3.95 CH3 _ C3 E~7--n I m.p. 6 o8 68.77 ~22 5d OQ~ocHcoN~lcF!~ ~ 75 ~ . _ >d 7 8 C ~.72 o8.09 4.30 C~l~ . _ ~ 19 -Table 1 (cont ' d) ~ . _ C~ m.p,6.68 68.77 41 22 55 a~e~oa~aoN~a~z ~ 111~
,\~ ~ 1 1 5'C 6.75 68.62 4.11 a~3 C~3 C2 H~ n25æ6~9 ô9.4414.05 5 6CL~--O C ~ C ON<
~ C~2 ~ 1.5561~.16 69~4~ '~89 a~3 l C~3 C" ~5 m.p.~.55 170.67~3.7s 57OQ~Oa~CON< 93~ l l "~ C~2~95C 733 j71.4213.89 ~,~13 . I - I
0~3 C2 ~ CH3 mP. 6.99 l69.4~ O5 58 CQ~3ocELcoN~R2~143~ ~ ¦
,144C 6.98168.7~14.0 C~3 _ ll ¦ CX~ C ~ ~5m~P- 1 6.99 69.d¢l~'.05 3 a~-o c~c oN~aE!2 ~C~3 123~ ¦
~ 124G 7.23 o9~7~ l2 ~,EI3 _ ¦ C_3 a~H~ CH30I m.p. 6.68160s7j3~7 60 ICQ~OC~CON~2~107~ ¦ ¦ ;
10 8C I o.6~l60.00',3.87 C:113_ __ ~

-- 20 ~

Table 1 (cont'd) _ _ a~ a~7-~
~ I m.p. 6.9g 69.45 4051 61 C ~ocHcoN~c~2~9 111~
, 1 1 3(~ '7.01 6916 4.12 a~3 _ l l m.p. ~.97 67.21 4~61 62 ~ ocHcoNHc~I2 ~ 78~
~< 7~ ~ 5.92 67.04 ~3 CQ _ C2~s , - I C H~ n2~ 634 68.02 4.41 63 ~ OC~CON< ,~ - D
~C ~ c~2-~ 15 5 8 ~6.46 68.41 g.l9 C2E~ H _ I C~ m.~. 6.34 68.02 ~Ll
6~ ~--ocHaoNHcE2 ~ ~) 94~
~ \~/ 9 6C 6~4 6~.38 4~38 ~ .. _ I
. C 2 ~5 5)C F~ 3 m.p . 6.04 6~6 ~20 6 5 ~--OC~ C ON~lC El2 @~ 86 ~
~\ 8'7 C 6.0'7 ô~L.5~ '.30 ~ C~ . _ ~ ~g ~ I ,~ m.~. 6.~)4 64.76 4'~0 6 6 ~=,~ O C H C O N ~I C H 2 ~/~ O C E~3 '7 5 ~ , ~ ' ~ 8 C 610 64.91 4~19 C~ ~
~ _ _ _ . . _ :

Table 1 (cont'd) __ _ l ~p. 537 6~1 4.6 67 a ~ 7 C c 10 67.40 450 C2~
l m.p. 6.34 ô~02 441 68 ~ - O c~c oNHcM ~ 89 ~
~ 9 1C ~40 68~0 4.20 C~ _C~3 _ _ ~50 ô.68 6~77 4~2 69 ~-O c ~a ON~ C~ 1.5661 ô.50 69.12 4.40 C C2 ~5 C2 ~5 n~ 6~34 6~2 ~.41 ~0 ~-OC~CON/ ~ 15611 6.40 67.90 ~30 C~5 _ _ ~ C2 ~'5 n~D o.ô8 68.77 422 71 ~OCECON< ~ 1.551O 6.5~ 67.~6 ~07 Cz~ r ~ CE2 -CE = C~2 n 2D6 45 69~6 4.07 72 ~ - O C E 50 N < ~ 1.557 S 6.~16 69.4~ 3~93 . C~ -T~ble 1 (cont'd) . . C 2 H~ _ __ I O CH~ n 26 6.04 6~76 4A20
7 5 ~)-0 G F~C o~r / ~3 1,5 5 2 6 6.02 64.2~ 4~25 C~
C 2 E 5 ~ _ _ l m.p.6.34 68.02 ~.41 74 ~OCEIC ON~LC~2 ~) 9 3 ~
~=~ ~ g 5~C 6.60 ô810 ~.20 C~
---- C H _ z s m.p. 634 68.0 4.41 7 5 ~ O C~CON~!C~L 2 ~) 7 d ~ ~ 6JG 6.30 68.00 4.20 .
C L CE~ ~
- C2~5 _ I ~ m.p. 654 68.02 76 ~--3CHCON~C~ CY3 8 8~
=/ - ~_ 9 0 C 6.40 681 14.20 ~ 9 _ __ C.,E~5 _ ~
~LO~ 6.0~ 6~7 ~ 0 '77 ~--O CEIC ONF' CE~2 ~ 7 5 ~
' CH30 7 6 C 6.06 ô~5 14.13 _ C O _ __ C.. Pg ~25 78 ~3--OC'rJGON~!CE~l ~3 156~6 6.0A 6_~7 1*.20 _ ~.96 6_.g I 3 9d __ j C~ bC~13 I _ ~

Table 1 ( cont ' d) -_ _ a2~B 2 / r~ I ~ n D 6-0d 64.7 ¦ g20 '7 9 ~ 0 C~IC ONX~El2~ O CEI~
a~ ~5 619 6.02 6~o 13.9 . _ ~~ C2 ~5 _ l m.p. o~58 65.60 4.03 ~oc~coN~CH2~3--0C2~s 40~
0~ 42C 610 65.40 3.80 C ! H 5 __ ~ I r~ m.~. 5.07 6Q5O gl 81 ~ \~OC~CONXCH2 ~ 80~
a ~ C ~ 8 2DC 5.01 59.82 41 C2 E~5 . _ I ~ ll 2 6 ~07 60.36 ~' .1
8 2 ~--O C H C 0 NP CH., ~/
~,Q ~ C~ 1.5695 5.~6 60.42 3.9 - ~EL3~ ,CE~3 _ .
CE~ ~ 2 æo 6.34 68.02 g.
85 ~3--OC~CONPC~z ~ ~, ~5 5 1 ô 6.60 67.80 a V .
C 3 X 7 n 11 2 4~0 84 ~--0cEcoNE~c~2 ~ 1.5557 6~4 68.02 4.~1 ~= crystai- 65 ¦ o7.85 42 C~ lized on _ af ter Table 1 (cont.'d) A~ ¦ C2 Hs ~ _ _ _ I m.p. ~97 67æl 4.61 CQ-~)--OCHCONHCEIt--~ 80~
~ 90'C 610 67~ 1~3 C 2 H s C~ a m .p . 634 68~0 1 4 86 C O ~ OCHCON~CE~ ~) 85~
88C 6.30 68~0 4.20 _ _ . _ C ~s I Z ~ C2 E~s m.p. 6.68 68.77 4 Z2 87 c e ~)--OC~CON/ 68~
~ CP2 ~ ~0C 6.76 68.S0 425 . __ C2~5 ~24~6 I C~2 -CP = CE~2 6.45 69~6 4.07 88 CQ/~3--OCPCON~ 1.5620 ~ \ C~2~ 6.60 69~ ~08 . _ _ C`,Ps - C 3 E7--i b ? 6.99 69.4~ ~' .05 89 CQ ~--OCPCON~ 177 ~ \ ~Y2 ~3 'C/r/~ 6.99 692 ~7 _ .
C7 H5 ~ m.p. 63~L 68.0 4.~1
9 0 C ~ ~--O CP C ON P C H2 ~ 108 ~
~ 109C ~.30 6~2 ~20 _ _ ~

Table 1 (cont ' d) _ _ a2 ~5 ~H3 I ~/ m.l~ . 6~ 68.02 4~4]
91 CQ~OCHCON~lCH2 ~ 91~ _ 93~C 6.30 6810 4.1 ll I
-- c~S aYl _ I ~ m.p. 6 04 64.~6 420 9 2 C Q~3--O C E C ONl~ C H2 ~\~ 101 ~
~=, lo2C 610 64~75 435 C2 H~ pCH~
I ~ m.p. 6.04 6~76 ~620 93 C Q~/~--OcHcoNHcE2 ~ g5--~, 37C 616 ô4.77 4.28 _ C~ 5 _ m.p. 6.04 6~6 aæo 9 4 CQ e3-- C EC ON HC ~z ~OCE3 9 8 ~
1aoC o6.02 ô4~7 413 C-,115 o~ l ~, m.p. . ~)'? 60.3~ 414 9 5 C ~)--O C EC ON H C E2 ~~ 105 ~
106C 510 60.20 4.00 _ l C~ Hs I
Tn ? ~0'7 603~ ~¢
9 6 CQ~3--OCEO ON~C~i~ ~--Cl 9 Z~
_ 9 3C 514 6~ 30 4.10 ~88~i~

Table 1 (cont'd) 02E~ C,l! .
I ~< m.p.433 54.79 5.76 9 7 CQ ~/ 3--O a H C ONH C H2 ~--CQ 8 9 ~
~ 9 O'C ~3 5g~5~ ~9 ___ C3~7-11 _ I ~ m~p.~3~L 68.02 9 8CQ~O CEO ONE~CH2 ~\~ 6 7~
7 O~c 6.54 67.96 4~60 _ C2P5 l m.p. 5.07 6036 ~14 9 9C~ ~ O C E~ C o NEC E~ 108 ~
Y - ~ 110C 4.gO 60.10 ~00 C2~5 C~3 20 100CQ~-OC~CON~C~ ~ 6. 5.4:4 61.37 3.98 C~æ 1.5608 5~40 6110 3.80 Cz P5 Cz Hs n 3 " 5.7~ 6~3C 3.8Z
101C~3--OCHCON~CE~ 1.~548 C~ 5.92 6231 5.70 _ C2 :~5 n D ~g 6137 338 102 CQ~--OC~CON< C~ _~ 1.5685 5.5 ¦61.5 ¦~.oo CQ _ ~

Tabl~ 1 (cont'd) __ _ _ C2 P-5 ~12S.6 I c~y--CE~=CH2 ~60 63.50 5.70 103 OQ-~OCPaoN/ 1.5652 ,~ CR 2 ~3 5~'7C 63 r7 5.66 _ _ .
I O O R--3 11 2 5.d 520 s8.7~ 3.80 104 a~-~ocE~aoN~ ~
c~ ~ ~5~80 5.12 58.9 3.65 C2 ~5 CH3 I \ m.p. 5.44 61.3 3.98 105 c o~oc~coN~a~2 ~ 122--~ 124~C 5.50 61.5 g.~0 CQ _ . C2 ~S C~3 m.p. 5~4 61~37 3.98
10 6 CQ~>--O C~C ONEC~2 ~ 101~
>~ ~103C 5.40 ôl.50 3.80 CQ
Cz ~5 _ l lm.p. 5. ~ ~ o61.37 3.98 107 cQ~--Oc:EicoNHc~2 ~C~3113-->=/114C 5~0 61.50 3.80 CQ _ _ .
C~ H5 CH3~, m.p. ;~46 58.54 3~79 10 8 CQ ~O C~ ~ ON~C~ 9 1 ~
CQ93C v~5 5~3.31 ~1 . , _ _ _ . _ -- ~ 8 Tab le 1 _( cont ' d ) _ _ _ _ _ _ C2 E~s OCH3 m.p.5 46 58.54 3.79 10 9aQ~o o ~c ON}lCE2 ~ 104~ . .
~ 105C516 58.53 ~81 _ CQ
C2 ~5 ,OGH3 m.p.5.32 57~29 3.52 110CL--~0 CYC ON:E~CE[~--~0~3 108~
a ~ 110C5~3 5~.98 3.~g _ Cz ~-~ CQ }n.p.~33 5~ 8 3.76 111C D P3--OC~CON~LCE2 ~ 87~ . .
>~ ~ 8 g ~C4.36 54.6~ 3.3~3 ~ _~ _ .
C 3 P 7 11 1. 5 6 ~ 2 5.44 61,37 3.98
11 2 C L--~ o C ~ C O N I~ C ~ 3 cry st al- 5.63 61~57 4 25 C Q ment_ __ C JL C~ 5 \ m.~ . 5 07 60~6 ~L1~' 113 ~q~ocaCONaCa2 ~ 122-- . _ c>=' 12~C 5;Ll 60 69 .1 1 ~ C2.~ ca3 m.p. 5.4~4 6~37 59 11 4 ~3--O C ~ C O N ~ C ~ ~ 101002 C 5~40 61.18 3.3 Cl _ _ _ i Table 1 ( cont ' d) _ ._. _ CQ a2 ~5 ~ I C ~ 3 ~ 2 s.0 5.44 61.3'7 3.98 115 ~/~OCHCON\
CQ CX2 ~? 1.5 6 6 9 5.50 61.50 4.00 _ .C ~ C2 ~5 CE3 ~ I ~ m.l~. 5.44 61.37 3.98 .
116 ~Oa~CONHCX ~ 135~
C ~ . 13~C 5.45 61.50 3~6 _ _ aQ C2 ~g CH
>r~ I ~ ~ m.p. 5A6 58.5~ 3.79 117 <~/ \~OCHCONXC~2 ~ 128~
C~ 1 29Çc 5.25 58.80 3.86 _ aQ cO x~ c~
>~ I ~ m.p. 4.33 5g.78 3.76 118 (/ \~OCE~CONHCX2 ~ \~ lLl~
~ ~ 1~2C 4.53 5~50 3.~1 CQ _ a g cO i~ C Q
~ I ~ m~?~ ~33 5478 3.76 119 ~' \?-OC~ICON~C~7 ~/ \~ 119~
~' ~ ~ 121 C433 5d~2 3.82 C~
_ c ~ a 3 r~ 7 ~
)~ I ~ m.~.5 44 61.37 338 120 ~OCXCON~C~2 ~/~ 102~
C~ 104 C ~g6 6L20 410 ~. . _ .

:~L8~G~

Table 1 (cont I d) -- C2E!~ _ _ I m.p. 5.07 6036 41 121 CQ~OC~lOONEC~ ~ 104~

CL 1~2Y-5 ~.'C 5.00 60.4C 4.
~ I m.p. 5.07 6Q.36 414
12 2 ~ O C~C ONEC:E~2 ~ 8 6 ~
~ t~Q 87~C 510 60.50 4.00 _. . . _ e 12 3 C2~ n Z5 613302 6~1 63~ 1 5.40 6 65 63.4~ 3 l~r 12 4 0 7'- ~ n 25 61.5658 6~2 65.4 1 5-~9 ~18 65~7 g~9~
Cz~l~j 7.01 70 3 15.13 125 ~9--oc~co~Eo~2¢;~ m.~62~5~C
,~= 6.9~ 69.9 14.98 ___ ~ 3 ~ ._ _ Table 1 (cont'd) __ _ C2Hsm.p.76~ 6.98 67.29 4.62 126 CH3~9--OCHCON:EICE2~3 ~ .
~ 80 C 7.04 67.22 4.55 C H 3 _ 1 2 7 ~ O C P C O N H C H 2~0Y m.p.78 ~ 7.37 71.05 g.87 80 C 7.14 '70.86 4.~7 . C H 3 . .

CH3 C2Hsm.~.84~ 6.98 67.29 g.62 128 \~--OCPCONHCH,~ _ .
CH3 86 ~ 7.08 6O.98 4.49 CP3 C2Hsm.p.71~ 7.43 ~2.45 9.39 129 ~ocHcoNHcE2 ~3 ~ N~73 C .7.43 72.29 9.23 C~i3 CH3 C2Hs ,~.p. 4~ 7.43 72.45 9.33 130 ~OCHCONPCH~9o . C-H3 97 C 7.47 7217 91o 3~7 Table 1 (cont'd) .~ _ _ _ _ _ Cz~ls 5.8 162.43 45 131 CHa4~--oa~ooNE!cH2~m.~54 ,\=/ 50C 5.91 ~26 4~5 aQ

1 3 20 P~ 3 ~/--O C P. C O NT;~ C E2 ~ m. p. 77790C 5 oC ~,93L g .~
__ _ _ C~5 m.p.100~ 53~ o2.43 g.55 1.33 CQ~7~ocEcoNl~cE2 o C
Y 102 61~ o~,.70 435 _ ~E~3 _ _ i . C- EI55 60 593a 4.33 I34 CQ~--oc~lcoN~LcE2~ m.~ 89~
. ~ 9 1 ~C 5~ ~ 413 CF~L3 . _ 1 3 5C ~ ~--o C E C O N E C E2 4~> m.~ 5 8~ 6.01 64.0 8.79 N-- 6 0 ~C 629 ~25 8.53 C23 _ _ ~8~7 Table 1 (cont'd) -~_ _ _ _ _ _ _ j a ~ 3 C2E~s ~ mp.101~ 6~2 163-4~ 4 136CQ~OCHOON~CH2 o 2 ¢É~ loC 6.3 163.4~ ~æ4 a~3 C2~$ m;p 105~ 597 60.4 ¦ ~L15
13~CQ~3ocEcoNxaE2--~3 107C
CH3 6 .00 6Q.04 4.09 --a ~ 3 c 2Hs _ >~ I /~ m.p99~ 6.36 64.9 1~.42 13 8 ca~/ \~~0 C ElC ONECE~ - \>
CH:s N~ 101 C 6.3 164.9 18.47 13 9 c,a -~0 C F~ C O NE C H2 -~ m.p 88 ~ 6.36 6'~9 1 ~3.42 ~ 32C 6A~L 6~1.oO 8.3r7 C H 3 C~H, m.~ ~ 6.3~; 64 a ¦ 8.~L~
140C~--OC;~CO~ECE~N 9C
C~ 12 6.3~ 64.7 18.~2 . . . ~ _ _ _ Table 1 (c t'd) _ _ _ I _ _ _ C2~[5 m.p.79-- 521 5815 4.52 141 ~OCHCONE[CE~ O
c~ S 80 C 5~8 ~7.89 4.61 C~ 2}~5 5~4g 61 ~3 ~L.77 142 ~oC~CONEl~E~2~ ~2~ 1.5433 ca 5.50 61.05 ~

C2~s m ~52-- 521 5815 4~2 143 ~OC~lC O~C~2~
C ~ 54 C 520 5~94 4.. 52 _ __ C.. H~ 5.62 63u05 919 144 ~/~oCHCONHC~243 ~D1.5610 ~ N 5~4 6~83 8.99 CQ

~ 5 5.62 63.05 915 145 ~oC~COMHC~2tg3 n23 15626 >=~ ~i 5.~1 62~6 ~.89 - _ . L l Table 1 (cont'd) _ _ _ ., _ Cl2E[5 ~ 5.62 6~05 91 1 4 6 ~3--O C E!C ON~0~2 ~N n~ 15 6 1 8 ~ 5.72 62.93 9.07 1 4 7C~--~3 0 C ~[ C O N H C E2 ~3 m.~ 88 ~ 5.49 61.33 4.77 8g~C 5.48 61~36 4.90 _ _ _ _ I

148 CQ--~OCHCONH5EI2~ mP.9700C 5.21 f8.15 ~52 5.24 57.8 4.61
14 9 CQ--~0 CHC O~T~C~2 ~3m.p.75~ 5.62 63.05 919 N--77 C 5 o5 63.03 9.20 ~ I ~73~ 43~ 52~i3 g.O7 150 ~ oC~lCON~lCE~
~ 75 ~, g~L 52.3~ 4~1 __ 5;) Table 1 (cont ' d) . _ _ _ _ _ , Q C2~s /r <I ~ m.p.65~ 4.76 56.65 ~26 1 51 ~O C HC ON EO E[2--~_ > C
~=~ U 65 79 s65a ~34 __ C C ~1 Q l2 5 m.plOO~ ~61 54.89 ~2~
1 5 2 ~ \~ O C E C O NE C~2 ~ 101C
,~ 4~3 5~67 ~17 . CP C2-75 1 5.3 ~ O C H C O N E G H2--~3 m .~11130C 4.39 52~53 4.0 7 CQ 11 ~Ll 5'~17 ~8 __ .
. C ) Cz~5m.plO5~ 4.76 50.o5 8.26 1 5 4 \~ O C EC ON :E~ C E2 ~> O
~ c N 107 C ~73 56.53 8.21 C~, , ~ _ 1 5 5 C~--~ O C EO ONE C E2--~ ~ ~2 ~ 4.61 5~89 4æ~7 _ a L 7~C ~54 57 .4 25 Table 1 (cont'd) __ _ _
15 6 a~--~oc~c ONECH~--~ m.p.82~ 439 5~33 4.07 C,1 8gC 4.39 5~11 ~07 _ C2E~3 _ .
15 7 CQ--~--OC:EIC oNHaEk~3 ~Lp.67~ 4.76 56.65 826 a Q 69~C 4.80 56~9 7 3 158 C Q--~OCHC ONECH2--~ n~ L5736 ~76 b6 65 826 C Q ~7 56.67 7.92 Cz~15 _ ~ I l m.~104~ 530 5920 9.21 1 5 9 ~ --O C HC ONY c Ez ~ o~ .
02N Oo ~, 5.32 58~g 915 .
C2~!1 ~ l ~ I /_ m.~108~ 5~70 l.Z8 3.36 1 6 0 ~/ \~o C T~ C ONE~ C ~2 ~Q /) o C
' 11 5.80 7LO9 597 :

Table 1 (cont'd) ~_ _ _ _ 6 1 ~ O C 1~ a O N ~ c ~2 ~3 ~p ~ 70 ~ 7.0r~ 7221 4a68 O~C~3 72 C 721 72A5 4~67 _ . __ 1 2~!im.p. 67~ ~.40 7;~ 4~L7
16 2 ~ooacONRCa2~3 o - ~ =76~ 7~37 7~62 6C1~3 ~H3 16 3 C2~s ~3m.p~ 63-- 7~07 72~21 4~68 CH 3 6d~ C r~O8 7210 ~75 l _ . C2ELs~1.55~4 7.0d: 69.28 g~25 1 64 ~cElcoNacH24T~
)~ ,Y~D3 69.0~ 4.26 CH3~ CH30 .
_ 16 5 0~ 3~m.D.72-- j7-07~.21~468 ¦

Table l (cont'd) __ I C 2H, .~ , ~ I ~ m.p.54~7.40 72.82 4.4 l 6 6aH3o -y \~ - O C ~ C ONH C H2 ~/ ~ ~o, . ~ ~ 50 ~, 719 72.~0 ~.3 CH: _, o C2E!5 ILD .86--7.42 74 31 ~13 l 6 7Cz~ 5 C -~ - o C E C 0 NE a ~ 2 ~3 8~C 7~ 73.98 _.09 C H s _ C zE[ ~ n~99 ~ 614 ô5.84 8.53 168o~3-~-ocEcoN~cEL2~ loo~C 6.17 65.88 8.50 .
. c2~ m~90 ~ ~75 ô4.96 8.91 169 ~ oC~CON~C~^2~ ~ 3C
'=~2 ~3 582 6~L75 8.80 170 s ~730C 6.1 65.84~8~3 N2 CH3 o 616 ~1~ i ~L~7 Table 1 (cont'd) -_ . _l 1~1 C2H5 m.p . 7 3 ~C 5.85 62.78 81 l N 0 2 CH 3 7 6 5.89 6Z.71 ~la I
_ I
C2Hs m.~ 114~ 5.75 64.96 8.91 1~ 2 ~ O CP CONHCH2~
02N~/ l.~oG 5.8g 6~.00 8.92 _ _ ll 50~ m?. 123~ 5.75 ô~96 8.91 1 ~ 3 o2N ~o C E~ c o N ~ c H2~ ~ -~ 125~, 5.7~ 6~L.68 8.8 _ C2~lsm.~135- 61~ 65.84 8.53 1~4 O~N-~oCHCON~IC~24~
~ ,~ 1'76C 6~0 65.74 8.53 1--- CE13 _ l l C2~ 'm.p. iO9~5.85 6~78 8.1.4 2~ -OC~cO~ElCEl2~3 1~.2'`
CH 3 0 ~ 5.90 o312 8.27 . . _ _ _ _ ~ _ _ Table 1 (con-t'd) l 7 6 ~ O C E10 ONHCH. ~~ m.~ 82-- 616 75~5 9.52 85C 6æ~3 ~3.52 9.4a _ 1 7 7 ~ O CH C O NY C H2 ~ m~Ea 79~ 6.31 71.06 4.8 F 82C 6~8 71.0~ A~6 1 2P 5m.plOO ~ 4.91 585~ 8.03 1~8 ~OC~ICONHCH~ ~No22'`
- ~10 ~, 4.90 58.32 7.98 C2~s m.~ 99~ 5.21 58.63 4.02 1~ 9 B r -~- O CHC ONE~CH2~
~ ~100 ~, 5æ6 5 8.76 ~0 3 180 I-~3-0 1 ~CO~C~?~m.~lltl~ '.59 51.~ 354 _112 C 4.6g 51,68 3.53 Table 1 (cont'd) ,,., . ~ _ l _ _ C~
~` I '33 ~4.0'.~3 4.15 . 181 ~ O C ~ C O ~ _ ~> n 2D3 1.V1~L6 : CF3 . .,.~ 1 -^ ~ .3 5 __ _ r~ 5 ~ ~ 5,7 4 6 4.9 ~ 3.9 7 1 8 2 ~ O C ~ C O ~J \ /~ n~ Sl1 9 ~ 2 ~ ~ 5.31 6 4.'7 S 3.'L 1 (~3 .
__ C~-~ ~ C-~-3 S.~ ~L 6 b9 v ~9 7 18 3 ~ \~--O V 'J V O `T L~ C ~ nD 1.5121 C~ ~ ~3 53 LL 6 _~ ~ 3.3 5 _ C~3 ~ ~.~ . v.~ 7 6 5.7 ' ~v 3 184 ~ OC~O`;--;~C 106~
v F 3 ~> 109 C 61 5 ~ 5.3 2 ~3 1 _ C ,Us C ~ :~ 5 6.0 7 o v~7 LL 5,Vx 3 1 8 5 ~ -0 C ~1C 0 `~ D, D 1.~1L~3 . C F ~ 2~ 6.0 3 v ~6 0 35 6 .~ _ _ _ Table .l ( con t ' d) _ _ _ _ . ___ ~ ~ C 3 .~ ~ -n o.3c oô.-~; 3.69 1 8 6 ~ ~--O C ~! C O `i~T ~ n 13;~ 1 .510 6 ~ ~ _ ~ ~.3~ 3 '1 .
C~3 __ _ C~:E!3 ~
~ I C3,-7 -i ô3~3 ~o.' 7 3.ô9 1 ~ 7 ~ O .~ ~ 1.5133 / C 2,~ a.a~ ~?ô~7 3.26 ~ F3 . _ _ _ __ C,r~
~ I ~E,~ o.3~ oo.~ :3.71 l $ 8 ~ ~)--3 C r~ n ~i~ 1~177 / \;~ ,3 ;~1~ ~7~)1 3~0 vF3 _ _ ,., ~ _ v i:' ~37 ~719 3~7~3 1 8 9 ~ O C ~ C 0 N \ ~ l~ 15217 ~J ~'-2~ \~ .~ 3~L O7 3~ .~, c~ 3 .~ . _ __ C~2~
I ~ o ., ,13 ~_~ ô:~l2 :'~31 190 ~--O C~C3~\ n2~,1.509~
~ `'~- ~ 52cs o2.09 3.92 CF3 _ . _ Table 1 (cont'd) 91 (~3-0I~lco~ m.~ 5.7~ 8~.as 97 CF3 C ~3 ~ 7 C ~ ~5 ~ 6~J ~)3 __ C-,~5 _ 5.7~ o~.95 3.~7 19 2 ~ O C ~ C O ~ ~ C ~ r~ D 1.514~3 ~/~3 \Ga3 o.3~ 6'.6~. 3.88 ~` 9 3 ~ , 0 .i~ 2 ~ . ~1 3, .,.7~' ~ 5 3.97 _! 1 0 7 C -- 3~ o _.50 3.87 C ~
/~ l C '~- 3 0.0~ o5.~4 3.
1 9 4 ~\~--O C E C O N ~ n 7~2 1.5204 C F3 C U 7--;~3 6.0 6 o5.~8 3.76 ~ C~-~5 _ _._ _ r ~ I C2r j ~38 oo.47 3.69 195 ~ 0 C~lCON\ ~ D' 1.5160 ~F~ CR~ 5v2 ôô.4~3 3.60 ~8~17 Table 1 (cont'd) _ _ ~ ~~ ~~~ ~~ ~~ ~~ ~~ ~~~ ~ 6.66 67.16 3.56 196 2 5 f 3 7 nD 1.5142 ~\ OE12 - ~ ' 6.02 66.85 3.45 _ CF3 CH3 _ 6 18 67.50 3.58 . C H CH -CH=CH 22 .
197 ~l2 5 / 2 2 nD 1.5209 CH ~ 6.17' 67.10 3.56 CH3 _ _ 198 ~ O CHCON \ nlD4 1.5t74 6.07 65.74 3.83 32 ~ C~13 6.03 65.46 3.66 '.' ,_, ._ . _ ,~ 12 5 / 2 5 6.38 66.47 3.69 199 ~ \ CH2 - ~ nD 1.5128 CF3 CH3 6.66 66.16 3.63 " . _ ._ C2H5 / C3H7-i 23 6.66 67.16 3.56 200 ~ O CHOCN nD 1.511 l ~2 ~ 6.59 66.89 3.20 ~ , _ __ _ .
~~ .

Table_ 1 ( cont ' d ) .__ ~ .... __ C2H5 / OE12-CH~I2 22 6~18 7.50 3.58 201 ~ O CHCON \ n D 1.5164 ~-- Cii~2 ~ 5.99 7.30 3.25 C 2H 5 _ _ _ 202 ~) CHCONHCH2 ~CH3 m p. 6.07 5.74 3.83 '~ 3 101C 6.15 5.95 3.83 , ~
C2H5 5.13 61.18 3.96 , 203 ~ O CHCONHCH --~ n2D5 1.51'69 CF3 CH3O 5.24 61.50 3.53 '1.', __ . -~ _ ; C 2H 5 ~ m.p . 5.13 61.18 3.96 204 ~O CHCONHCH2`~ 63 ~
CF 3 OCH3 65C 5.08 61.38 3.71 _ C H
~ 1 2 5 ~ m.p. 5.13 51.18 3.96 205 ~O CHCONHCH2--~\ 72 ~
, __ 73C 5 27 61.12 3 74 8~

Ta~le 1 (~on~

_ ~ .. . _ - .~ _ C2H5 CH 5.82 62.98 3 ~ 67 206 ~O C H C O ~ nlD6 1.5217 ~ 'CH2 - ~ 5.94 62.77 3.41 CF3 CH o ~ _ 12 5 l2 5 6.12 63.78 3.57, 207 ~ - O C H C O N nlD5 1.5181 CF 3 CH2~ 6.26 63.55 3.34 _ CH ~O _ _ _ _ 208 ~ OCHCONHCH 2~ 72 - 4.76 59.83 3.67 , 3 73C 4.36 60.10 3.75 . _ _ _ _ 209 ~ OCHCONHCH2 - ~ 66 - 4.61 58.15 3.77 3 68C 4.72 57.92 3.69 ~. _ C12H5 m.p. 4.61 58.15 3.77 , 210 ~ OCHCONHCH2 - ~CQ 90 ~
~F 3 92C 4.28 5i .85 3.71 _ = .-.... _ _~_ _ ~ I .
, "~

Table 1 Icont'd) ~ ~ _ _ ....... __ _ C2H5 CH3 4.76 9.83 3.67 ,, 211 ~ O~HCON nD1.5243 ; CF3 \CH'' ~ 5.01 9.76 3.39 . _ _ C2H5 3.97 3.22 3.45 212~ OlHCONHCH - ~ Q nD 1.5274 3 Q 3.89 3.15 3.22 _ _ ,. ... _ - _ __ l2H5 m.p. 4.70 5.96 .08 ; 213~ OCHCONHCH2 ~ ~ 56 ~
CF3 58C 4.52 5.96 .13 I' _ .
' F2 5 / 3 5.08 7.13 .92 214 ~ OCHCON \ ~ D 1.5225 CF3 2 S 5.05 6.92 3.69 `............... .

2H5 / C2H5 14 5.43 8.20 3.77 , 215 ~ OCHCON\ ~ D 1.5212 ~; ~ _ 5.45 ;7.96 3.60 i.

~ I .

~`'`' Table 1 (cont'd) __ ~ _ _ __ __ .

216 ~ C12 5 ~ n D 1.4930 .93 58.71 4.2 CF3 4.76 58.81 4.0 ~ _~ .
' IC2H5 ~ m.p. 5.07 0.35 3.28 217 ~OCHCONHCH2 ~ 60 - 62C l CF3 _ 4.90 jO .4S 3.38 .~ . __ . .

218 ~ 12 5_~ n2D 1.5148 5.07 0.35 B .28 CF3 5.04 0.17 7.69 I~ . _ _ _ _ 219 ~ C 2H 5 ~n D 1.512 5.07 0.35 8.28 CF 3 4.83 0.15 B .03 _ L~ 741~4 94 ~ 99 .

.~

Table 1 (cont ' d) ~ __. __ . -C3H7 -n /CH 6.07 65.74 3.83 221 ~O C H C O N~ 3 nlDl 1.5162 CF3 C~2~ 5.97 65.09 3.79 _ ¦ C 3 H 7 - n ~ _ ; 222 ~ O C H C O N H C H2~ 86C 6.07 65.74 3.83 CF 3 CH3 6.07 65.79 4.14 C 337 n 223 ~ O C H C O N H C H2~ 55C 6.07 65.74 3.83 CF 3 CH3 5.98 65.81 3.98 _ C 3H 7 -n _ _ ~ _ 224 ~ - O C H C O N H C H2~ m p 4.96 59.15 3.63 CF 3 CQ 67C 4 ~ 95 58.94 3.81 _ C 3H 7 -n 225 ~O C H C O N H C H2 ~ 57C 5.43 61.35 7.95 ~L ~`~

Table 1 (cont ' d) ~ ____ _ C2H m~p . 4.61 58.14 3.77 226 CQ - ~ O ~ H C O N H C H2 - ~ 99350C
CF 3 4.56 57.94 3.76 _ I __ _ _ __ 227 CQ ~ O C2H5C f 3 nD 1.526 4.96 59.15 3.63 CF3 \ CH2~ 4.84 59.35 3.41 . _ _ 228 C Q - ~ C H C O N n D 1.5254 5.29 60.07 3.50 CF 3 CH 2~5.23 59.44 3.51 '~ ,, ._ __ _ _ ., 229 C Q - ~O C H C O N / n 1.5310 5.14 61.24 3.40 CF 3 25.13 60.94 3.38 , _ _ _ C2H5CH2-C_CH 4.67 61.54 3.42 230 Q ~ O C H C O N \ nl9 1.5320 CF3 2 4.69 61.18 3~33 ,. ~ _ t , Table 1 (cont'd) __ __ _ C2H C H -i 15 4 5.6¦60.94 3.39 2 31 C Q ~ O ~HCON / 3 7 D- 1.528 CF 3 CH 2--~ 5.81 60 . 77 3.52 ___ _ , _ _ C12H 5 m . p O4 . 96 59.15 3 . 63 232C Q ~O CHCONHCEI ~3 10 7 ~
~ 2 ~ 109C , CF 3 CH 3 4.9 59.34 3 . 87 _.. r _ _ C2H5 4.9 59.15 3.63 233CQ ~{) CHC~ONHCH2~ mjp CF 3 CH3 99C 4 . 8 59 . 23 3.66 _ , _ , , _ _ __ _ C2H5 4.9 59.15 3.63 234CQ --~ O CHCONHCH2~ ~H3 mlipl.~
CF 3 113C4.8 59.02 3 . 68 . _ _ _ IC2H5 m.p. 4.7 56.79 3.49 235 CQ ~ OCHCONHCH2~ 9980C
CF 3CH 3O 4.6 56.52 3 . 4 8 ,_ _ _ ........ -. _ ~ 53 -Table 1 (cont'd) _ _ __ __ _ C H
~2 5 ,_~ m.p. 4.77 56.79 .49 ! 236 CQ~/ \~ O CHCONHCH2 ~/ \) gg f-OCH3 100C 4.70 56.77 3.52 CF3 _ ~ - _ ~ __ .
237 CQ- ~ CHCONHCH2 ~ CH3 72 ~ 4.77 56.79 .49 CF 74C 4.71 57.01 .60 ,, _ _ 3 _ _ /15-41.536 5.09 57.76 .37 238 C~- ~ O CHCON \ ~ D 4.91 57.93 .60 CF3 C~3 O
~' __ ~ ___ _ _ C H m.p. 3.97 53.21 .45 239 ~ 12 5 _ ~ 113C 3.90 53.12 .45 _ _ _ _ C2~ m.p. .97 53.21 .45 ,~ L ! ~ ~r ~ ~ Q _ l460C3 95 53 50 3 53 ) ,... _ . I

. . ~ ~

Table 1 ( cont ' d ) ___ ~ ' '7 _ __ _ C2H5 m.p. 3.97 53.21 3.45 241 CQ ~O CHCONHCH ~ CQ 99 _ CF 2 101C 3.89 53~06 3.45 ~ - ~ _ ~ _ 2 5 / 3 15.4 4.32 54.30 3.33 242 C~ O1HCON~ $3 D 15421 4.51 54.65 3.35 ,,... _ . ~ _ IC2H 5 m . p . 4.00 50.86 3.71 243CQ ~ O CHCONHCH2l~3 89 ~
CF3 S 91C 4.04 51.00 3.74 ll . ,,.................... _ _ _ _ C12H5 m.p. 4.18 53.12 3.57 244CQ ~ O CHCONHCH2~ 76 ~
CF 78C 4.22 53.16 3.95 _ 3 _ C2H5 ~ m.p. 4.33 54.77 7.52 245C Q ~ O CHCON~CH ~ 71 ~

L 730C 4 3( 55 0l7 52 Table 1 (cont'd) -_ __ . __ _ _ C H
~ 2 5 r-~ 19 4.33 54.77 7.52 296 C ~ O CHCONHCH2- ~ ~ nD 1.522 l CF3 4.33 54.29 7O37 ~ __ _ _ C2H5 19 4.33 54.77 7.52 247CQ ~ CHCONHCH2 ~nD 1.522 4.34~ 54.87 7.47 ~ _ ..... ~ _ _. _ C3H7 n m.p.4.96 59.15 3~63 248CQ ~ O CHCONHCH2 ~ 72 ~4.96 59.00 3.96 i C 3 .. ~ _. _ C3H -n 11 S 29 60.07 3.50 249 CQ ~ O CHCON ~ CH - ~ nD 1~.5290 .
CF3 2 ~=~ 5.20 60.27 3.45 _C3H7 -n 250CQ- ~ O CHCONHCH2- ~ 74 ~ 4.69 55.89 7.24 77 C 4 67 ~6.~3 7.6~

.

The phenoxyalkylamide derivative according to ~his invention can be prepared by the reaction (1) or t2) illustrated below.

(1) ~ ~ O-CHCO-A ~ HN <
Y ~ CH-Z
p3 Base ~ n ~ O-C~CON ~
-HA \CH-Z

(2) n ~ OH + A-C3CON <

Base ~ ~ ~ O-CHCON ~
Y ~ CH-Z

(In the above formulas (1) and (2), A represents a chlorine atom or a bromine atom; and X, n, Y, Z, Rl, R2 and R3 have the same meanings as defined above.) The above-mentioned reactions (1) and (2) may suitably be carried out by the addition of a weak base such as pyridine, triethylamine, sodium carbonate or potassium ~L~89~i~7 carbonate in the presence of an appropriate solvent.
As the solvent used in the reaction, there may be mentioned, for example, an aromatic hydrocarbon such as benzene, toluene and xylene; an ether such as diethyl ether, tetrahydroEuran and dloxane; and a ketone such as methyl ethyl ketone and dimethyl ketone. Parti-cularly, in the reaction (2), an ether or a ke-tone may preferably be used. While the reaction temperature which depends upon the kind of the reagent and solvent used for the reaction is not critical, the reaction (1) may preferably be conducted at a temperature of 0 to 30C, and the reaction (2), at a temperature of 50 to 130C.

The reaction time usually is for about 1 hour to 10 hours.

Next, Examples for syntheses of the amide derivatives according to the present invention will be described below.

Synthesis Example 1. Synthesis of N-benzyl-2-(3,5-dimeth 1 henoxv)-butyramide (compound of Compd. No. 30 Y P ~ ~
in Table 1 shown above) In 30 mQ of benzene were dissolved 1.8 g (0.017 mole) of benzylamine and 1.2 g (0.015 mole) of pyridine, and thereto was added dropwise 3.0 g (0.013 mole) of 2-(3~5-dimethylphenoxy)-butyroyl chloride at room tem-perature with stirring. After the reaction was carried out for 5 hours, the reaction mixture was washed with water, dilute hydrochloric acid, dilute aqueous sodium hydroxide and then water successively. After the benzene layer was dried, the benzene was removed by distillation. The resultant crude crystals were ~8~

recrystallized from n-hexane to give 2.4 g of N-benzyl-2-(3,5-dimethylphenoxy)-butyramide melting at 93 - 94C
as color]ess needles.

~nthesis Example 2. Synthesis of N-(2-methylbenzyl)-2-(3,5-dichlorophenoxy)-butyram~de (compound of Compd.
No. 116 in Table l shown above) In 30 mQ of benzene were dissolved 1.5 g (0.012 mole) of 2-methylbenzylamine and 1.0 g (0.01 mole) of triethyl-amine, and thereto was added dropwise 2.8 g (0.01 mole) of 2-(3,5-dichlorophenoxy)-butyroyl chloride in 20 mQ
benzene solution at room temperature with stirring.
After the reaction carried out for 2 hours, the reac-tion mixture was washed with dilute hydrochloric acid, dilute aqueous sodium hydroxide and then water suc-cessively. After the benzene layer was dried, the benzene was removed by distillation.

The resu~tant crude crystals were recrystallized from ethanol to give 2.3 g of N-(2-methylbenzyl)-2-(3,5-dichlorophenoxy)-butyramide melting at 135 ~ 137C as colorless prisms.

Synthesis Example 3. Synthesis of N-benzyl-2-(4-chloro-3-methylphenoxy)-valeramide (compound of Compd. ~o. 54 in Table l_shown above) In 60 mQ of acetone were dissolved 3.5 g (0.013 mole) 25 of N-benzyl-~-bromovaleramide and 6.3 g (0.040 mole) of 4-chloro-3-methylphenol, and thereto was added 6.9 g (0.050 mole)of anhydrous potassium carbonate, and then the resultant mixture was boiled under reflux with stirring for 10 hours.

After cooling, the acetone was removed by distillation and then lO0 mQ of wa~er was added to the residue. The thus precipitated oily substance was extracted with benæene.

AEter the benzene layer was washed with dilute hydro-chloric acid, dilute aqueous sodium hydroxide and then water, and then dried, the benzene was removed by distillation. The residue was subjected to silica gel column chromatography to obtain 3.0 g of N-benzyl-2-(4-chloro-3-methylphenoxy)-valeramide as colorless oil.

The oil crystallized when allowed to stand at room temperature, and the so obtained crystals showed a melting point of 75 ~ 78C.

Synthesis Example 4. Synthesis o N-thienylmethyl-2-(4-chloro-3,5-dimethylphenoxy)-butyrarnide (compound of Compd. No. 137 in Table 1 shown above) In 50 mQ of benzene were dissolved 1.6 g (0.014 mole) of 2-aminomethylthiophene and 1.4 g (0.014 mole) of tri-ethylamine, and thereto was added dropwise a solution of 3.1 g (0.012 mole) of 2-(4-chloro-3,5-dimethyl-phenoxy)-butyroyl chloride in 20 m~ of benzene at room temperature with stirring. After the mixture was stirred for 1 hour and left to stand overnight, the reaction mixture was washed with water, dilute hydro-chloric acid, dilute aqueous sodiurn hydroxide and then water successively. After the benzene layer was dried, the benzene was removed by distillation.

The resultant crude crystals were recrystallized from ethanol to give 3.0 g of N-thienylmethyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide melting at 105 ~ 107C
as colorless needles.

5ynthesis Example 5. Synthesis of N-(2-pyridylmethyl)-2-(3-chlorophenoxy)-butyramide (compound of Compd. No.
144 in Table 1 shown above) In 50 mQ of toluene were dissolved 1.6 g (0.012 mole) o~ 2-aminomethylpyridine and 1.2 g (0.012 mole) of tri-ethylamine, and thereto was added dropwise a solution 2.8 g (0.012 mole) of 2-(3-chlorophenoxy)-butyroyl chlori.de in 20 mQ of toluene at room temperature with stirring. After the reaction was carried out for 4 hours, the reaction mixture was washed with water, dilute aqueous sodium hydroxide and then water suc-cessively. After the toluene layer was dried, the toluene was removed by distillation. The thus obtained oil was subjected to column chromatography to give 2.3 ' g of N-(2-pyridylmethyl)-2-(3-chlorophenoxy)-butyramide showing n2D6 1.5610 as pale yellow oily liquid.

Synthesis Example 6. Synthesis of N-furfuryl-2-(4-chloro-3-methylphenoxy)-butyramide (compound of Compd.
No. 133 in Table 1 shown above) 20 In 50 mQ of benzene were dissolved 1.5 g (0.015 mole) of furfurylamine and 4.0 g (0.051 mole) of pyridine, and thereto was added dropwise a solution of 3~0 g (0.012 mole) of 2-(4-chloro-3-methylphenoxy)-butyroyl chloride in 20 mQ of benzene at room temperature with stirring, followed by stirring for further 5 hours.
Subsequently, after the same procedure as in Synthesis Example 4 and 5 was followed, the resultant crude crystals were recrystallized from ethanol to give 1.0 g of N-furfuryl-2-(4-chloro-3-methylphenoxy)-butyr-30 amide melting at 100 ~ 102C as pale brown needles.

Synthesis Example 7. Syn hesis of N-benzyl-2-(3-- 61 ~

methoxyphen~ )-butyramlde (compound of Compd. No. 163 in Table 1 shown above) In 50 mQ of toluene were disso]ved 1.7 g (0.013 mole) of benzylamlne and 1.0 g (0.013 mole) oE pyridine, and thereto was added dropwise a solution oE 2.9 g (0.013 mole) of 2-(3-methoxyphenyl)-butyroyl chloride in 20 mQ
of toluene at room temperature with stirring.

After the reaction was carried out for 1 hour and the reaction mixture was left to stand overnight, it was washed with water, dilute hydrochloric acid, dilute aqueous sodium hydroxide and then water successively.
After the toluene layer was dried, the toluene was - removed by distillation. The resultant crude crystals were recrystallized from ethanol to give 1.6 y of N-benzyl-2-(3-methoxyphenoxy)-butyramide melting at 63 64C as colorless needles.

Synthesis Example 8. S~nthesis of N-benzyl-2-(3-nitrophenoxy)-butyramide (compound of Compd. No. 172 in Table 1 shown above) 20 In 30 mQ of toluene were dissolved 1.6 g (0.015 mole) of benzylamine and 1.2 g (0.015 mole) of pyridine, and thereto was added dropwise a solution of 3.1 g (0.013 mole) of 2-(3-nitropheno~y)-butyroyl chloride in 30 m~
of toluene at room temperature with stirring. Sub-sequently, after the same procedure as in Synthesis Example 7 was followed, the resultant crude crystals were recrystallized from e~hanol to give 2.4 g of N-benzyl-2-(3-nitrophenoxy)-butyramide melting at 114 ~ 116C as pale yellow needles.

Synthesis Example 9. Synthesis of N-(2=me~ benzyl?-2-(4-nitrophenoxy)-butyramide (compound of Compd. No.
175 in Table 1 shown above) -In 50 mQ of toluene were dissolved 1.9 g (0.014 mole) of 2-methoxybenzylamine and 1.2 g (0.015 mole) of pyridine. Then, was added dropwise thereto a solution oE 2.8 g (0.012 mole) of 2-(4-nitrophenoxy)-butyroyl chloride in 30 mQ of toluene and the mixture was treat-ed according to the same procedure as in Synthesis Example 7. The resultant crude crystals were recry-stallized from ethanol to give 2.4 g of N-(2-methoxybenzyl)-2-(4-nitrophenoxy)-butyramide melting at 109 ~ 112C
as colorless needles.

Synthesis Example 10. Synthesis of N-(2-chlorobenzyl)-2-(3-trifluoromethylphenoxy)-butyramide (compound of Com d No. 209 in Table 1 shown above) P _ In 50 mQ of toluene were dissolved 1.6 g (0.011 mole) of 2-chlorobenzylamine and 1.0 g (0.013 mole) of pyri-dine, a~d thereto was added dropwise a solution of 2.5 g (0.009 mole) of 2-(3-trifluoromethylphenoxy)-butyroyl chloride in 20 m~ of toluene at room tem-perature with stirring. After the mixture was stirred for 1 hour and left to stand overnight, the reaction mixture was washed with water, dilute hydrochloric acid, dilute aqueous sodium hydroxide and then water successively. After the toluene layer was dried, the toluene was removed by distillation.

The resultant crude crystals were recrystallized from ethanol to give 1.7 g of N-(2-chlorobenzyl)-2-(3-tri-fluoromethylphenoxy)-butyramide melting at 66 68C as colorless needles.

Synthesis Example 11. Synthesis of N-benzyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide (compound of Com d No. 226 in Table 1 shown above) p In 50 mQ of toluene were dissolved 1.6 g (0.015 mole) of benzylamlne and 2.4 g (0.030 mole) of pyridine.
Then, was added dropwise thereto a solution or 3.0 g (0.010 mole) of 2-(4-chloro-3-trlfluoromethylphenoxy)-butyroyl chloride in 30 mQ of toluene and the mixture was treated, according to the same procedure as in Synthesis Example 10. The resultant crude crystals were recrystallized from ethanol to give 1.6 g of ~-benzyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide melting at 93 ~ 95C as colorless needles.

Synthesis Example 12. Synthesis of N-(4-pyridylmet yl)-2-(4-chloro-3-trifluorometh~lphenoxy)-butyramide (com-pound of Compd. No. 247 in Table 1 shown above) In 50 mQ of toluene were dissolved 1.3 g (0.012 mole)of 4-(aminomethyl)pyridine and 1.0 g (0.010 mole) of triethylamine. Thereto was added dropwise a solution of 3.0 g (0.010 mole) of 2-(4-chloro-3-trifluoro-methylphenoxy)-butyroyl chloride in 30 mQ of toluene at room temperature with stirring, and the mixture was treated according to the same procedure as in Synthesis Example 10. The resultant oily substance was subjected to silica gel column chromatography by eluting with 25 toluene to obtain 1.6 g of N-(4-pyridylmethyl)-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide showing n D 1.5228 as pale yellow oil.

~n another aspect of this invention, there is provided a herbicidal composition which comprises as an active ingredient the phenoxyalkylamide derivative of the above formula (I) and an agriculturally acceptable carrier and method of use of the same.

When the phenoxyalkylamide derivative according to the present invention is to be applied as a herbicide, the deriva~ive may be formulated for use to the preparations oE any form commonly employed as a herbicide, for example, dusts, granules, wettable powders, emulsifiable con-centrates, water soluble powders, liquid formulations, aerosols, fumigants and so on, with admixture of such an inert carrier as solid carrier, liquid carrier and emulsifying dispersant and, if required, other auxiliary agents.

As the inert carrier, there may be mentioned any of solid, liquid or gaseous carriers oridinarily employed in the art for herbicides and, for example, talc, clay, kaolin, diatomaceous earth, calcium carbonate, potassium chlorate, saltpeter, wood powder, white carbon, nitrocellulose, starch, benzene, xylene, n-hexane, gum arabic, vinyl chloride, carbon dioxide, fleon, propane, butane, bentonite, methylnaphthalene, cyclohexanone, isophoron and the like.

The herbicidal composition of this invention may also optionally be blended with any auxiliary agents for preparation, for example, spreaders, diluents, surface active agents, solvents and the like as usually done in the art.

~oreover, the herbicidal composition of this invention may also be admixed with other herbicides, fungicides, insecticides, other agricultural chemicals, fertilizers, e.g. urea, ammonium sulfate, ammonium phosphate, potas-sic fertilizers, soil conditioners and the like.

As the herbicides which may advantageously be admixed with the compound of formula (I), there may be mentioned a thiocarbama-te -type herbicide such as Benthlocarb (Saturn), Molinate (Ordram), etc.; an acid amide type herbicide such as Alachlor (Rasso), Butachlor (Machete), etc.; a phenoxy type herbicide such as 2,~-PA, MCP, etc.; a diphenyl ether type herbicide such as Ni-trofen (NIP), Chlornitrofen (MO), etc.; a urea type herbicide such as Diuron (Karmex D), Linuron (Afalon), etc.; a triazine type herbicide such as Simazin (Prinsep), Afrazin (Gesaprim), etc.; and other herbicides such as Trifluorolin (Treflan), Oxadiazon (Rons-tar), ACN
(~ogeton), Bentaron (Basagran), etc.

The above-mentioned carriers and various auxiliary agents may be optionally utilized alone or in combina-tion therewith for desired purposes.

In general, the herbicidal composition of this inven-tion may contain the phenoxyalkylamide derivative in an amount of 0.1 ~ 90% by weight, based upon the finished composition and the content of the active derivative in a herbicidal composition may usually depend upon the preparation form to be formulated, for instance, ordinarily 0.1 ~ 50 parts by weight for dusts, 0.1 ~ 70 parts by weight for wettable powders, 0.1 ~ 50 parts by weight for granules, 0.1 ~ 70 parts by weight for emulsifiable concentrates and the like.

While the amount of the herbicidal composition to be applied to a field is defferent depending upon the method of use, the place for use and a kind of object weeds, it usually is 0.5 ~ 100 g/are, preferably 1 50 g/are with respect to the active ingredient, i.e~
the amide derivative of this invention.

:~8~6~

Next, Examples of the preparation of the present herbi-cidal composition are given below. All parts are given by weight hereinafter unless otherwise stated.

Herbicidal composition 1 50 parts oE N-benzyl-2-(3,5-dimethylphenoxy)-butyramide (compound of Compd. No. 30), 40 parts of xylene and 10 parts of SORPOL ~00 (trade name: surface active agent) were homogeneously blen-ded and dissolved to obtain an emulsifiable concentrate.

Herblcidal composition 2 50 parts of N-(2-methylbenzyl)-2-(3,5-dichlorophenoxy)-butyramide (compound of Compd. No. 116), 30 parts of kaolin, 15 parts of bentonite and 5 parts of sodium lignosulfonate were homogeneously blended and pulve-rized to obtain a wettable powder.

Herbicidal composition 3 7 parts of N-benzyl-2-(3-chlorophenoxy)-buiyramide (compound of Compd. No. 67), 60 parts of bentonite, 30 parts of talc and 3 parts of sodium naphthalenesulfonate ~o were homogeneously blended and pulverized. To the blend was added a small amount of water and the mixture was kneaded, granulated by using a granulating machine and dried to give granules.

Herbicidal composition 4 25 50 parts of N-thienylmethyl~2-(3,4-dichlorophenoxy)-butyramide (compound of Compd. No. 156), 40 parts of xylene and SORPOL 800 (trade name: surface active ~L8~

agent) were homogenerously blended and dissolved to obtain an emulsifiable concentrate.

~Ierbicical composi-tion 5 50 parts oE ~-(2-pyridylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide (compound of Compd. No.
138), 30 parts oE kaolin, 15 parts of bentonite and 5 parts of sodlum ltgnosulEonate were homogeneously blended and pulverized to obtain a wet-table powder.

~Ierbicidal composition 6 7 parts of N-furfuryl-2-(4-chloro-3-methylphenoxy)-butyramide (compound of Compd. No. 133), 60 parts of bentonite, 30 parts of talc and 3 parts of sodium naphthalenesulfonate were homogeneously blended and pulverized. To the blend was added a small amount of water and the mixture was kneaded, granulated by using a granulating machine and dried to give granules.

Herbicidal composition 7 50 parts of N-benzyl-2-(3-methoxyphenoxy)-butyramide (compound of Compd. No. 163), 40 parts of xylene and 20 10 parts of SOP~POL 800 (trade name: surface active agent) were homogeneously blended and dissolved to obtain an emulsifiable concentrate.

Herbicidal composition 8 50 parts of N-benzyl-2-(3-nitrophenoxy)-butyramide 25 (compound of Compd. No. 172), 30 parts of kaolin, 15 parts of bentonite and 5 parts of sodium lignosulfonate were homogeneously blended and pulverized to give a wettable powder.
~!

- 6~ -Herbicidal composition 9 7 parts of N-benzyl-2-(4-methyl-3-nitrophenoxy)-butyr-amide (compound oE Compd. No. 168), 60 parts of bento-nite, 30 parts of talc and 3 parts of sodium naphthalne-sulfonate were homogeneously blended and pulverized.To the blend was added a small amount of water and the mi~ture was kneaded, granulated by using a granulating machine and dried to give granules.

Herbicidal composition 10 50 parts of N-benzyl-2-(3-trifluoromethylphenoxy)-butyramide (compound of Compd. No. 181), 40 parts of xylene and 10 parts of SORPOL 800 (trade name: surface active agent) were blended and dissolved to obtain an emulsifiable concentrate.

Herbicidal composition 11 50 parts of N-benzyl-2-(4-chloro-3-trifluoromethyl-phenoxy)-butyramide tcompound of Compd. No. 226), 30 parts of kaolin, 15 parts of bentonite and 5 parts of sodium lignosulfonate were homogeneously blended and pulverized to obtain a wettable powder.

Herbicidal composition 12 7 parts of N-furfuryl-2-(4-chloro-3-trifluoromethyl-phenoxy)-butyramide (compound of Compd. No. 244), 60 parts of bentonite, 30 parts of talc and 3 parts of sodium naphthalenesulfonate were homogeneously blended and pulverized. To the blend was added a small amount of water and the mixture was kneaded, granulated by using of a granulating machine and dried to give granules.

The herhicidal composition of this invention exhibits excellent herbicidal effect agains~ not only broad leaved weeds but also other weeds by the chlorosis action, and it shows little phytotoxicity against rice plants and others due to the auxin action which is observed in conventional phenoxy series herbici.dal com-positions known to the art. Moreover, the h~rbicidal composition of this invention has no toxicity against man, beast, fishes and shellfishes and no bad smell at all.

Next, the effects of the herbicidal composition accord-ing to the present invention will be explained concretely by way of Experiments shown below. The number of each test compound in each Experiment is the same as that in Table l shown above.

Experiment l Soil treatment tests for padd~ field weed Pots, each having an area of l/9000 are, were packed with paddy soil (diluvial soil) and planted with uni-formly mixed seeds of barnyardgrass (Echinoeh~oacrusgaZli), of broad leaved weeds (Rot~a indica Koekne, Lindernia Py~idaria. L., Monochoria vaginaZis), of Scripus hotarui Oh~i. and of Cyperus difformis L. upon the surface layer, and tuber of Sagittaria pygmaea Miq.
or Cyperus serotinus Rottb. and rice plant seedlings at 1.8 ~ 3 leaf stage were also transplanted. Then, the pots were filled with water to a depth of 2 ~ 3 cm.

Then, 3 days later, i.e., at the initial stage of generation of each weed, a predetermined amount of dilute solution of a wettable powder of each test compound, which had been prepared in the same manner as in ~lerbicidal composition 2 above, was uniformly spread to the surface of filled water.

Four wee~s aEter the treatment, the herbicldal effects oE each test compound were investigated.

The results are shown in Table 2 wherein the herbicidal effects are evaluated according to the rating system as defined below:

5 = All killed; 4 = Severely damaged;
3 = Modera-tely damaged; 2 = Slightly damaged;
l = Minor damaged; 0 = None (normal development) The data on the upper and lower lines in each column of Table 2 are the results which were obtained by carrying out the experiments at concentrations of an active ingredient of 50 g/are and 25 g/are, respectively (with regard to compounds of Compd. Nos. 1 to 180), and at concentrations of an active ingredient of 25 g/are and 12.5 g/are, respectively (with regard to compounds of Compd. Nos. 131 to 250).

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Experiment 2 Soll treatment tests for upland weed control Pots, each having an area of 1/5000 are, were packed with upland soil (diluvial soil) and then seeds of corn, of soybean, of wheat, of barnyard millet (Ech~nochZoa utiZis Ohwi.), of large crabgrass (Digitaria adscendens Henr.J, oE clover, of common purslane (Po~tuZaca oZeracea L.), of barnyardgrass (EchinochZoa crusgaZZi Beauv.), or of redroot pigweed (Amaranthus retrofZe~us l.) were sowed therein. After covering with soil, a predeter-mined amount of a dilute solution of each wettable powder, which had been prepared in the same manner as in Herbicidal composition 2 above, was uniformly spread by using a pressure sprayer.

Three weeks after the treatment, the herbicidal effects of each test compound were investigated.

The results are shown in Table 3 wherein the same rating system as defined in Experiment 1 is applied.

The data on the upper and lower lines in each column of Table 3 show the results which were obtained by carrying out the experiments at concentrations of an active ingredient oE 50 g/are and 25 g/are, respectively.

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~)OZ _ ~1 ,_1 ,_1 ~1 ~1 ~`I ,_i t~l t~

From the experimental results shown above, it is under-stood that the herbicidal composition of this invention is highly harmless to various crops and shows excellent herbicidal effects agalnst various kinds of weeds, and S it is recognized that the herbicidal composition of this invention is an extremely excellent selective herbi-cidal composition.

Experiment 3 Foliar spread test for upland weed control 10 Pots, each having an area of 1/15500 are, were packed with upland soil (diluvial soil) and then planted with wheat, barnyard millet, large crabgrass and redroot pigweed.

When each plant grew up to 2 ~ 3 leaf stage, a O.S0~ by lS weight (wt %) or 0.25 wt % solution of each wettable powder, which had been prepared in the same manner as in Herbidical composition 2 above, was spread for treat-ment by using a pressure sprayer.

Two wee~s after the treatment, ther herbicidal effects of each test compound were investigated.

The results are shown in Table ~ wherein the same rating system as defined in Experiment 1 is applied.

The data on the upper and lower lines in each column of Table 4 show the results which were obtained by carrying out the experiments at concentrations of an active ingredient of O.S0 wt ~ and 0.25 wt ~, respectively.

- 9~ -Table 4 Com- Phytotoxlcity ~ Herbicidal eEfects pound _ agair st crops ~ 1 redroot No. wheat millet crabgrass pi~weed .
129 ~ O 2 3 r ~

176 1 0 1 1 l s5 I S

From the experimental results shown above, it is understood that the herbicidal composition of this invention is highly harmless to crops and shows excel-lent herbicidal effects against various kinds of weeds, S and it is recognized that the herbicidal composition of this invention is an extremely excellent selective herbicidal composition.

Claims (17)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A phenoxyalkylamide derivative represented by the fomula wherein X: a lower-alkyl group, a lower-alkoxy group, a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;
Z: a phenyl group, a substituted phenyl group represented by the following formula (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom; and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group or a furyl group;
R1: a lower-alkyl group;
R2: a hydrogen atom, a lower-alkyl group, a lower alkenyl group, a lower-alkynyl group or a lower-alkoxy group; and R3: a hydrogen atom or a lower-alkyl group.
2. A phenoxyalkylamide derivative as defined in Claim 1, represented by the formula wherein X': a methyl group or a chlorine atom;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3,X's may be the same or different;
Y': a hydrogen atom or a trifluoromethyl group;
Z': a phenyl group, a 2-methylphenyl group, a 2-chlorophenyl group, a thienyl group, a 2-pyridyl group or a 3-pyridyl group;
R1': an ethyl group or a n-propyl group; and R2': a hydrogen atom or a methyl group.
3. A phenoxyalkylamide derivative according to Claim 2, wherein the phenoxyalkylamide derivative is selected from the group consisting of the compounds shown below:

N-Benzyl-2-(4-chloro-3-methylphenoxy)-butyramide N-Benzyl-N-methyl-2-(4-chloro-3-methylphenoxy)-butyramide N-Benzyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-Benzyl-N-methyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-(2-methylbenzyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-Benzyl-2-(3,4-dichlorophenoxy)-butyramide N-Benzyl-2-(3,4-dichlorophenoxy)-valeramide N-(2-Pyridylmethyl)-2-(3,5-dimethylphenoxy)-butyramide N-Thienylmethyl-2-(4-chloro-3-methylphenoxy)-butyramide N-Thienylmethyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-(2-Pyridylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-(3-Pyridylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-Benzyl-2-(3-trifluoromethylphenoxy)-butyramide N-(2-Chlorobenzyl)-2-(3-trifluoromethylphenoxy)-butyramide N-Thienylmethyl-2-(3-trifluoromethylphenoxy)-butyramide N-Benzyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide N-Benzyl-N-methyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide N-(3-Pyridylmethyl)-2-(4-chloro-3-trifluoromethyl-phenoxy)-butyramide
4. A process for preparing a phenoxyalkylamide derivative represented by the formula wherein X: a lower-alkyl group, a lower-alkoxy group a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;
Z: a phenyl group, a substituted phenyl group represented by the following formula (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom; and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group or a furyl group;
R1: a lower-alkyl group;
R2: a hydrogen atom, a lower-alkyl group, a lower-alkenyl group, a lower-alkynyl group or a lower-alkoxy group; and R3: a hydrogen atom or a lower-alkyl group, which comprises reacting a compound represented by the formula wherein A represents a chlorine atom or a bromine atom; and X, n, Y and R1 have the same meanings as defined above, with a compound represented by the formula wherein Z, R2 and R3 have the same meanings as defined above, in a solvent in the presence of a base.
5. A process for preparing a phenoxyalkylamide derivative according to Claim 4, wherein said base is at least one selected from the group consisting of pyridine, triethyl-amine, sodium carbonate and potassium carbonate.
6. A process for preparing a phenoxyalkylamide derivative according to Claim 4, wherein said solvent is at least one selected from the group consisting of benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, methyl ethyl ketone and dimethyl ketone.
7. A process for preparing a phenoxyalkylamide derivative according to Claim 4, wherein the reaction is carried out at a temperature of 0 to 30°C.
8. A process for preparing a phenoxyalkylamide derivative represented by the formula wherein X: a lower-alkyl group, a lower-alkoxy group, a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;
Z: a phenyl group, a substituted phenyl group represented by the following formula (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom; and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group or a furyl group;
R1: a lower-alkyl group;
R2: a hydrogen atom, a lower-alkyl group, a lower-alkenyl group, a lower-alkynyl group or a lower-alkoxy group; and R3: a hydrogen atom or a lower-alkyl group, which comprises reacting a compound represented by the formula wherein X, n and Y have the same meanings as defined above, with a compound represented by the formula wherein A represents a chlorine atom or a bromine atom; and Z, R1, R2 and R3 have the same meanings as defined above, in a solvent in the presence of a base.
9. A process for preparing a phenoxyalkylamide derivative according to Calim 8, wherein said base is at least one selected from the group consisting of pyridine, triethyl-amine, sodium carbonate and potassium carbonate.
10. A process for preparing a phenoxyalkylamide derivative according to Claim 8, wherein said solvent is at least one selected from the group consisting of benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, methyl ethyl ketone and dimethyl ketone.
11. A process for preparing a phenoxyalkylamide derivative according to Claim 8, wherein the reaction is carried out at a temperature of 50 to 130°C.
12. A process for preparing a phenoxyalkylamide derivative represented by the formula wherein X: a lower-alkyl group, a lower-alkoxy group a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;
Z: a phenyl group, a substituted phenyl group represented by the following formula (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom; and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group or a furyl group;
R1: a lower-alkyl group;
R2: a hydrogen atom, a lower-alkyl group, a lower-alkenyl group, a lower-alkynyl group or a lower-alkoxy group; and R3: a hydrogen atom or a lower-alkyl group, which comprises reacting a compound represented by the formula wherein L represents a group of or a hydrogen atom;
(in which A represents a chlorine atom or a bromine atom; and R1 has the same meaning as defined above), and X, n and Y have the same meanings as defined above, with a compound represented by the formula wherein M represents a hydrogen atom or a group of ;
(in which A and R1 have the same meanings as defined above), and A, R2 and R3 have the same meanings as defined above, provided that when L is , M is a hydrogen atom and when L is a hydrogen atom, M is , in a solvent in the presence of a base.
13. A process for preparing a phonoxyalkylamide derivative according to Claim 12, wherein the reaction is carried out at a temperature of 0 to 30°C when L and M
in the formula represent a group of and a hydrogen atom, respectively, and the reaction is carried out at a temperature of 50 to 130°C when L and M represent a hydrogen atom and a group of , respectively.
14. A method for controlling weeds which comprises applying to such weeds an effective amount of a phenoxy-alkylamide compound having the formula wherein X: a lower-alkyl group, a lower-alkoxy group, a halogen atom, a cyano group, a nitro group or a propionyl group;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, Xs may be the same or different;
Y: a hydrogen atom, a lower-alkyl group, a lower-alkoxy group, a trifluoromethyl group or a nitro group;
Z: a phenyl group, a substituted phenyl group represented by the following formula (in which R4 represents a lower-alkyl group, a lower-alkoxy group, a nitro group or a halogen atom; and m is an integer of 1 or 2, provided that, when m is 2, R4s may be the same or different), a naphthyl group, a thienyl group, a pyridyl group or a furyl group;
R1: a lower-alkyl group;
R2: a hydrogen atom, a lower-alkyl group, a lower-alkenyl group, a lower-alkynyl group or a lower-alkoxy group; and R3: a hydrogen atom or a lower-alkyl group.
15. A method for controlling weeds as defined in Claim 14, wherein the phenoxyalkylamide derivative is represented by the formula wherein X': a methyl group or a chlorine atom;
n: an integer of 0 to 3, provided that, when n is an integer of 2 or 3, X's may be the same or different;
Y': a hydrogen atom or a trifluoromethyl group;
Z': a phenyl group, a 2-methylphenyl group, a 2-chlorophenyl group, a thienyl group, a 2-pyridyl group or a 3-pyridyl group;
R1': an ethyl group or a n-propyl group; and R2': a hydrogen atom or a methyl group.
16. A method for controlling weeds as defined in Claim 14, wherein the phenoxyalkylamide derivative is selected from the group consisting of the compounds shown below:

N-Benzyl-2-(4-chloro-3-methylphenoxy)-butyramide N-Benzyl-N-methyl-2-(4-chloro-3-methylphenoxy)-butyr-amide N-Benzyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-Benzyl-N-methyl-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-(2-Methylbenzyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-Benzyl-2-(3,4-dichlorophenoxy)-butyramide N-Benzyl-2-(3,4-dichlorophenoxy)-valeramide N-(2-Pyridylmethyl)-2-(3,5-dimethylphenoxy)-butyramide N-Thienylmethyl-2-(4-chloro-3-methylphenoxy)-butyramide N-Thienylmethyl-2-(4-chloro-3,5-dimethylphenoxy)-butyr-amide N-(2-Pyridylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-(3-Pyridylmethyl)-2-(4-chloro-3,5-dimethylphenoxy)-butyramide N-Benzyl-2-(3-trifluoromethylphenoxy)-butyramide N-(2-Chlorobenzyl)-2-(3-trifluoromethylphenoxy)-butyr-amide N-Thienylmethyl-2-(3-trifluoromethylphenoxy)-butyramide N-Benzyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyr-amide N-Benzyl-N-methyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide N-(3-Pyridylmethyl)-2-(4-chloro-3-trifluoromethyl-phenoxy)-butyramide.
17. A method for controlling weeds according to Claim 14, wherein the amount of the phenoxyalkylamide derivative is in the range between 0.5 g/are and 100 g/are.
CA000413389A 1981-10-20 1982-10-14 Phenoxyalkylamide derivative, process for preparing the same, herbicidal composition containing the same and method for controlling weeds by the use of the same Expired CA1188697A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP16634381A JPS5867653A (en) 1981-10-20 1981-10-20 Benzylamide derivative of phenoxyalkanoic acid and herbicide
JP166343/1981 1981-10-20
JP209946/1981 1981-12-28
JP20994681A JPS58113156A (en) 1981-12-28 1981-12-28 Phenoxyalkanoic acid benzylamide derivative and herbicide
JP209945/1981 1981-12-28
JP20994581A JPS58113155A (en) 1981-12-28 1981-12-28 Amide derivative of phenoxyalkanoic acid and herbicide

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GB8710362D0 (en) * 1987-05-01 1987-06-03 Shell Int Research Anilide herbicides
CA2091864C (en) * 1992-03-26 1999-09-07 Tomokazu Hino Process for producing halogenophenoxyfatty acid derivatives by selective halogenation and halogenophenoxyfatty acid derivatives
WO2006129164A1 (en) 2005-05-31 2006-12-07 Pfizer Japan Inc. Substituted aryloxy-n-bicyclomethyl acetamide compounds as vr1 antagonists

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GB2005668B (en) * 1977-09-14 1982-05-26 Shell Int Research Herbicides
AR220917A1 (en) * 1977-10-26 1980-12-15 Stauffer Chemical Co N-SUBSTITUTE-2- (4 SUBSTITUTE-3,5-DIMETHYLPHENOXY) COMPOUNDS USEFUL AS ANUBLICIDES AND COMPOSITION CONTAINING THEM
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