CA2034404A1 - Uracil derivatives and pesticides containing the same as active ingredient - Google Patents

Uracil derivatives and pesticides containing the same as active ingredient

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Publication number
CA2034404A1
CA2034404A1 CA002034404A CA2034404A CA2034404A1 CA 2034404 A1 CA2034404 A1 CA 2034404A1 CA 002034404 A CA002034404 A CA 002034404A CA 2034404 A CA2034404 A CA 2034404A CA 2034404 A1 CA2034404 A1 CA 2034404A1
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CA
Canada
Prior art keywords
group
substituted
phenyl
substituents
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002034404A
Other languages
French (fr)
Inventor
Shigeru Ishii
Kazunari Nakayama
Kazuo Yagi
Jun Satow
Kenzou Fukuda
Kaoru Itoh
Toshiyuki Umehara
Masaki Kudo
Yoichi Inoue
Tsutomu Nawamaki
Shigeomi Watanabe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nissan Chemical Corp
Original Assignee
Nissan Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Publication of CA2034404A1 publication Critical patent/CA2034404A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

The present invention provides novel uracil derivatives and pesticides which contain the novel uracil derivatives as an active ingredient, and exhibit preventing and controlling effects against harmful living things, especially agricultural insect pests, sanitary insect pests, stored product insect pests, house insect pests and veterinary insect pests at a very low drug-concentration.

Description

DEMANDES OU BREVETS VOLUMINEUX

LA PRÉSENTE PARTIE DE CETTE DEMANDE OU CE BREVET
COMPREND PLUS D'UN TOME.

CECI EST LE TOME ~ DE ~

NOTE: Pour les tomes additionels, veuillez contacter le Bureau canadien des breveta , ~ ~ ~

JUMBO APPLICATIONS/PATENTS

THIS SECTION OF THE APPLICATION/PATENT CONTAINS MORE
THAN ONE VOLUME
~, . THIS IS VOLUME / OF -2 NOTE: For addltlonal volume~ plea~e contact the Canadlan Patent Offlce ,, ' - -TITLE OF THE INVENTION
URACIL DERIVATIVES AND PESTICIDES CONTAINING THE
SAME AS ACTIVE INGREDIENT

BACKGROUND OF THE INVENTION
The present invention relates to novel uracil derivatives and pesticides which contains the said derivatives as active ingredient.
Disclosures about the uracil compounds have been made in several patents and prior art literatures. For example, 3,6-diphenyluracil and 3-phenyl-6-(3-bromo-4-methoxyphenyl)uracil are disclosed in Journal of American Chemical Society, Vol. 58, p. 299, 1935. Also, 3,6-diphenyluracil is disclosed in Chemical Abstract, Vol.
52, 6364h, 1958.
However, there is no disclosure of activity of the said compounds against living things in the said literatures.
In U.S. Patent Nos. 3,580,913, 3,869,457 and 3,981,715, there are disclosed the uracil compounds having at 6-position of the uracil ring a trifluoromethyl group and at 3-position thereof a substituted or non-substituted phenyl group, but in these compounds the number of the substituents in the phenyl group is up to 2 and there is no disclosure of uracil compound having the phenyl group which has 3 or more substituents. Also, in 203440~

these patents, there is no disclosure about preventing and controlling effects to insect pests of the said compounds.
In U.S. Patent Nos. 4,746,352, 4,760,163, 4,859,229, and 4,812,164 and International Patent Publication Nos.
WO 88-10254, WO 89-02891 and WO 89-03825, there are disclosed the uracil compounds in which the 6-position of the uracil ring is hydrogen atom, a C1_4 alkyl group or a C1_4 fluoroalkyl group and the 3-position thereof is a phenyl group which has three substituents at the 2-, 4-and 5-positions, but in these compounds the substituent at the 5-position of the phenyl group is defined to be the one linked by oxygen atom or a carbonyl group.
Further, there is no disclosure about preventing and controlling effects to insect pests of the said compounds in these patents.
Warming-up of the earth and spread of heating systems have created an environment which encourages the activity of various species of insect pests or allows them to stay active all the year around. The thus widened scope of activity of insect pests is giving serious lnfluence on the life of human beings. Thus, the development of a compound which shows high efficacy against various species of insect pests at an extremely low dosage (drug-concentration) and glves no baneful influence to mammals and other useful living things has been eagerly desired.

-:

As a result of extensive and intensive researches for obtaining a compound which is satisfied with the above requests, it has been found that uracil derivatives obtained by reacting a compound represented by the formula:

X OR (XXXVI) '~` A N-H

(wherein Rl, R2, z2 and A are as defined in Claim 1, and R7 represents Cl_6 alkyl group, benzyl group or phenyl group) and a compound represented by the formula (IV) or (V):

zl B-NCZ B-NHCOR
(IV) (V) ,~ (wherein B and zl are as defined in Claim 1, and Ra represents C1_6 alkyl group, benzyl group or phenyl group) exhibit preventing and controlling effects (pesticidal effect) against various species of insect pests such as agricultural insect pests, sanitary insect pests, stored product insect pests, house insect pests and veterinary insect pests at a very low drug-concentration and are no fear of giving and damage to the mammals, fishes, crustaceans and useful insects. The present invention was attained on the basis of this finding.

,' , ,. . ~
~ . .

SUMMARY OF THE INVENTION
In a first aspect of the present invention, there is provided uracil derivatives represented by the general formula (I):

~N-B
)l N l~Z l ( I ) wherein R1 represents hydrogen atom, C1-4 alkyl group, C2-4 alkenyl group, C2_4 alkynyl group, C1-4 haloalkyl group, C2_4 alkoxyalkyl group, formyl group, C2_6 alkylcarbonyl group, C2_6 alkoxycarbonyl group, C3-6 alkoxycarbonylalkyl group, C2_6 cyanoalkyl group, benzyl group, phenyl group, -SR12 group [wherein R12 is C2-6 alkoxycarbonyl group, C1_6 alkylsulfonyl group, -NR13R14 group (wherein R13 is C1_6 alkyl group and R14 is C1-6 alkyl group, C2-6 alkoxycarbonyl group, C3_g alkoxycarbonylalkyl group, C1_6 alkylsulfonyl group, C2_6 alkylcarbonyl group, C3_g dialkylaminocarbonyl group, C2_6 dialkylaminosulfonyl group and phenyl group which may be substituted or non-substituted) and phenyl group which may be substituted or non-substituted (the substituent is selected from halogen atom, cyano group, nitro group, C1_4 alkyl group, C1_4 ~ ..' ::

. ~
: -ZO;~4~04 haloalkyl group, C1_4 alkoxy group, C2_6 alkoxycarbonylgroup, C1_4 haloalkoxy group, C2_6 haloalkoxycarbonyl group, C2_6 alkylcarbonyl group, C2_6 haloalkylcarbonyl group, C1_4 alkylsulfonyl group or C1_4 haloalkyl sulfonyl group, and when the number of the substituents is not less than 2, the substituents may be same or different)], alkali metal or alkaline earth metal;
R2 represents hydrogen atom, halogen atom, C1_4 alkyl group, C1_4 haloalkyl group, C1_4 hydroxyalkyl group, C2-4 alkoxyalkyl group, C2_4 altylthioalkyl group, thiol group, C1_4 alkylthio group, C1_4 alkylsulfinyl group, C1_4 alkylsulfonyl group, C1_4 haloalkylthio group, C1_4 haloalkylsulfinyl group, C1_4 haloalkylsulfonyl group, hydroxyl group, C1_4 alkoxy group, C1_4 haloalkoxy group, formyl group, cyano group, nitro group or thiocyanate group;
zl and z2 represent independently oxygen atom, sulfur atom or imino group;

A represents ~ [wherein X is halogen atom, C1_4 alkyl group, C1-4 alkoxy group, C1_4 alkylthio group, C1_4 haloalkyl group, C1-4 haloalkoxy group, C1-4 haloalkylthio group, amino group, cyano group or nltro group, and I is an integer of O to 5 (when I is an integer of 2 to 5, the substituents X may be same or different)], or naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl .~ .

group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituent of the above aromatic group is selected from halogen atom, Cl_g alkyl group, C1_4 alkoxy group, Cl_4 alkylthio group, C1_4 haloalkyl group, C1-4 haloalkoxy group, Cl_4 haloalkylthio group, amino group, cyano group and nitro group, and when the number of the substituents is not less than 2, these substituents may be same or different), C1_6 haloalkyl group containing one or more fluorine atom, halogen atom, cyano group, nitro group, C1_6 alkylthio group, C1_6 alkylsulfinyl group, C1_6 alkylsulfonyl group, C1_6 haloalkylthio group, C1_6 haloalkylsulfinyl group, C1_6 haloalkylsulfonyl group, C1_6 alkoxy group, C1_6 haloalkoxy group, or C2_6 alkoxycarbonyl group; and when A is ~ (where X and I are as defined above), or naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituents of the above ' - 7 - z034~04 aromatic groups are the same as defined above), B is Ylm ~ [wherein yl is halogen atom, C1_6 alkyl group, C2-6 alkenyl group, C2_6 alkynyl group, C3-6 cycloalkyl group, C1_6 haloalkyl group, C2_6 haloalkenyl group, C2_6 haloalkynyl group, C3-6 halocycloalkyl group, C2_6 cyanoalkyl group, C1-6 hydroxyalkyl group, C2_6 carboxyalkyl group, C1_6 alkoxy group, C2_6 alkenyloxy group, C2_6 alkynyloxy group, C3-6 cycloalkyloxy group, C1_6 haloalkoxy group, C2-6 haloalkenyloxy group, C2_6 haloalkynyloxy group, C3-6 halocycloalkoxy group, C4-7 halocycloalkylalkoxy group, C1_6 alkylthio group, C2-6 alkenylthio group, C2_6 alkynylthio group, C3-6 cycloalkylthio group, C1_6 haloalkylthio group, C1_6 alkylsulfinyl group, C2_6 alkenylsulfinyl group, C2-6 alkynylsulfinyl group, C3-6 cycloalkylsulfinyl group, C1_6 haloalkylsulfinyl, C1_6 alkylsulfonyl group, C2-6 alkenylsulfonyl group, C2_6 alkynylsulfonyl group, C3-6 cycloalkylsulfonyl group, C1_6 haloalkylsulfonyl group, C2_6 alkoxyalkyl group, C2-6 alkoxyalkoxy group, C2-6 haloalkoxyalkyl group, C2_6 haloalkoxyalkoxy group, C2-6 alkylthioalkyl group, C2_6 alkylthioalkoxy group, C3-6 alkoxycarbonylalkyl group, C3-6 alkylcarbonylalkyl group, C2_6 alkoxycarbonyloxy group, C2_6 alkylcarbonyl group, C3-6 alkenylcarbonyl group, C3-6 alkynylcarbonyl group, C4_7 cycloalkylcarbonyl group, C2_6 haloalkylcarbonyl - 8 - 20~

group, C2_6 alkoxycarbonyl group, C2_6 haloalkoxycarbonyl group, C3-6 alkoxycarbonylalkoxy group, nitro group, cyano group, hydroxyl group, carboxyl group, thiocyanate group, isothiocyanate group, C2_6 thiocyanatealkyl group, C1_6 alkylsulfonyloxy group, C2_6 alkylthiocarbonyl group, amino group (-NR3R4), aminocarbonyl group (-CoNR3R4), aminocarbonyloxy group (-oCoNR3R4), amide group (-NR3CoR4), alkoxycarbonylamino group (-NR3C02R4), aminosulfonyl group (-So2NR3R4), thioamide group (-NR3CSR4), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group, trimethylsilyl group or -~ W ~ Ar group (wherein W is IR5 1l IRs IR5 IR
-O-, -S-, -N-, -C-, -C- -O-C- -C-O- -N-C- -CH-CH- -C=C-(O) q R R6 1 6 R6 R3 R6 Rs R6 R R

O S
Il 11 -O-CH-CH- -N-C-N- -N-C-N--C 9 C-, -N=N-, Rs R6 R3 R4 1 3 R4 ' -O-CH-CH-O- -CH-O-N=C-I 5 1 6 , or 1 5 ¦ ( in which R3 and R4 represent independently hydrogen atom, C1_6 alkyl group, C2_6 alkenyl group, C2_6 alkynyl group, C1_6 haloalkyl group, C2-6 haloalkenyl group, C2_6 haloalkynyl group, C2_6 alkylcarbonyl group, C2_6 alkoxycarbonyl group, phenyl group or benzyl group; R5 and R6 represent independently hydrogen atom, halogen atom, Cl-6 alkyl group, C3-6 ~ ~ .
,, ; '' ' ~"'`"' ~ ' ~

cycloalkyl group, cyano group or phenyl group; and q is an integer of O to 2); n is an integer of O or l; and Ar is phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group which may be substituted or non-substituted (the substituent of the above aromatic groups is selected from halogen atom, cyano group, nitro group, C1_4 alkyl group, C1_4 haloalkyl group, C1_4 alkoxy group, C1_4 haloalkoxy group, C1_4 alkylthio group, C1_4 haloalkylthio group, C1_4 alkylsulfonyl group, C1_4 haloalkylsulfonyl group, C2_4 alkoxycarbonyl group, carboxyl group, amino group, Cl_4 monoalkylamino group, C2_g dialkylamino group, phenyl group, benzyl group, methylenedioxy group or ....
halomethylenedioxy group, and when the number of the substituents is not less than 2, the substituents may be same or different)); and m is an integer of O to 5 (when it is 2 to 5, the substituents yl may be same or different)], or naphtyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimizyl group, pyrazyl 203440~

group, quinolyl group, quinoxalyl group, benzofuryl group, benzothienyl group, indolyl group, benzoxazolyl group or benzothiazolyl group which may be substituted or non-substituted (the substituent of the above aromatic groups is selected from halogen atom, cyano group, nitro group, C1_g alkyl group, C1-4 haloalkyl group, C1_4 alkoxy group, C1_4 haloalkoxy group, C1_4 alkylthio group, C1_4 ,~ haloalkylthio group, Cl_4 alkylsulfonyl group, Cl_4 haloalkylsulfonyl group, C2_4 alkoxycarbonyl group, carboxyl group, amino group, C1_4 monoalkylamino group, C2_g dialkylamino group, phenyl group, phenoxy group or benzyl group, and when the number of the substituents is 2 or more, the substituents may be same or different), and when A is C1_6 haloalkyl group containing one or more fluorine atoms, halogen atom, cyano group, nitro group, C1_6 alkylthio group, C1_6 alkylsulfinyl group, C1_6 alkylsulfonyl group, C1_6 haloalkylthio group, C1_6 r ) haloalkylsulfinyl group, C1_6 haloalkylsulfonyl group, C1_6 alkoxy group, C1_6 haloalkoxy group or C2_6 alkoxycarbonyl group, B is ~ [wherein y2 is halogen atom, C1-4 alkyl group, C1_4 alkoxy group, C1-4 haloalkyl group, C1_4 haloalkoxy group, C1_4 alkylthio group, C1-4 haloalkylthio group, C1_4 alkylsulfinyl group, C1_4 haloalkylsufinyl group, C1-4 alkylsulfonyl group, :
.

- li - 203A40~

Cl_4 haloalkylsulfonyl group, sulfonamide group, C2_4 alkenyl group, C2_4 haloalkenyl group, amino group, Cl_4 monoalkylamino group, C2_8 dialkylamino group, C2_6 alkoxyalkoxy group, C2_6 alkoxycarbonyl group, cyano group or nitro group, and r is an integer of 3 to 5 (the substituents y2 may be same or different, and when r = 3 with the substituents at the 2-, 4- and 5-positions, the substituent y2 at the 5-position is not Cl-4 alkoxy group, Cl_4 haloalkoxy group, C2_6 alkoxyalkoxy group or C2_6 alkoxycarbonyl group)], provided that A is not phenyl group and 3-bromo-4-methoxyphenyl group, when B is phenyl group.
In a second aspect of the present invention, there is provided pesticides comprising as an active ingredient a pesticidally effective amount of at least one of the uracil derivatives set forth in the first aspect.
In a third aspect of the present invention, there is provided a process for producing the uracil derivatives set forth in the first aspect, which comprises reacting compounds represented by the general formula (XXXVI):

Rj~oR7 ~XXXVI) A l_H
Rl (wherein Rl, R2, z2 and A are as defined above, and R7 re-presents C1_6 alkyl group, benzyl group or phenyl group) with compounds represented by the general formula (IV) or (V):

B-NCZ B-NHCOR
(IV) (V) (wherein B and zl are as defined above, and R8 represents C1_6 alkyl group, benzyl group or phenyl group).

DET~ILED DESCRIPTION OF THE INVENTION
Uracil derivatives represented by the formula (I) according to the present invention are the compounds useful as active ingredient of pesticides.
The term "pesticides" used in the specification of the present invention means a composition having preventing and controlling effects to harmful living things, in particular, insecticidal, acaricidal, nematicidal and molluslcidal compositions and herbicidal composition.
Among the uracil derivatives represented by the formula (I), (1) compounds of the formula (I) wherein /~ Xl A is ~ ~wherein X is halogen atom, C1_4 alkyl group, C1_4 alkoxy group, C1_4 alkylthio group, Cl-4 haloalkyl group, C1_4 haloalkoxy group, C1_4 haloalkylthio group, amino group, cyano group or nitro group, and I is an integer of 0-5 (when I is an integer of 2 to 5, the \
- : ' . .

. ~ .

.
~ ; .

substituents X may be same or different)], or naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituent of the above aromatic group is selected from halogen atom, C1_4 alkyl group, Cl_4 alkoxy group, C1_4 alkylthio group, C1_4 haloalkyl group, Cl_4 haloalkoxy group, C1_4 haloalkylthio group, amino group, cyano group and nitro group, and when the number of the substituents is not less than 2, these substituents may be same or different), and Ylm B is ~ [wherein yl is halogen atom, C1_6 alkyl group, C2_6 alkenyl group, C2-6 alkynyl group, C3-6 cycloalkyl group, C1_6 haloalkyl group, C2_6 haloalkenyl group, C2_6 haloalkynyl group, C3-6 halocycloalkyl group, C2_6 cyanoalkyl group, C1_6 hydroxyalkyl group, C2-6 carboxyalkyl group, C1_6 alkoxy group, C2_6 alkenyloxy group, C~-6 alkynyloxy group, C3-6 cycloalkyloxy group, C1_6 haloalkoxy group, C2-6 haloalkenyloxy group, C2-6 haloalkinyloxy group, C3-6 halocycloalkoxy group, C4-7 halocycloalkylalkoxy group, C1_6 alkylthio group, C2-6 alkenylthio group, C2_6 alkynylthio group, C3-6 .

cycloalkylthio group, C1_6 haloalkylthio group, C1_6 alkylsulfinyl group, C2_6 alkenylsulfinyl group, C2_6 alkynylsulfinyl group, C3-6 cycloalkylsulfinyl group, C1_6 haloalkylsulfinyl, C1_6 alkylsulfonyl group, C2_6 alkenylsulfonyl group, C2_6 alkynylsulfonyl group, C3-6 cycloalkylsulfonyl group, C1_6 haloalkylsulfonyl group, C2_6 alkoxyalkyl group, C2_6 alkoxyalkoxy group, C2_6 haloalkoxyalkyl group, C2_6 haloalkoxyalkoxy group, C2_6 alkylthioalkyl group, C2_6 alkylthioalkoxy group, C3-6 alkoxycarbonylalkyl group, C3-6 alkylcarbonylalkyl group, C2_6 alkoxycarbonyloxy group, C2_6 alkylcarbonyl group, C3-6 alkenylcarbonyl group, C3-6 alkynylcarbonyl group, C4_7 cycloalkylcarbonyl group, C2_6 haloalkylcarbonyl group, C2_6 alkoxycarbonyl group, C2_6 haloalkoxycarbonyl group, C3-6 alkoxycarbonylalkoxy group, nitro group, cyano group, hydroxyl group, carboxyl group, thiocyanate group, isothiocyanate group, C2_6 thiocyanatealkyl group, C1_6 alkylsulfonyloxy group, C2_6 alkylthiocarbonyl group, amino group (-NR3R4), aminocarbonyl group (-CoNR3R4), aminocarbonyloxy group (-oCoNR3R4), amide group (-NR3CoR4), alkoxycarbonylamino group (-NR3Co2R4), aminosulfonyl group (-So2NR3R4), thioamide group (-NR3CSR4), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group, trimethylsilyl group or -~ W ~ Ar group (wherein W is . . :

, ~

- 15 - 203~40~

-O-,-S-,-N-,-C-,-C- -O-C- -C-O- -N-C- -CH-CH- -C=C-(O)q R R R R5 R3R6 R5 l6 R5l6' ll 11 -O-CH-CH- -N-C-N- -N-C-N--C -- C-, -N = N-, R R6 R3 R4 l3 R4' -O-CH-CH-O- -CH-O-N=C-R R6 R5 ¦ (in which R3 and R4 represent independently hydrogen atom, Cl-6 alkyl group, C2-6 alkenyl group, C2_6 alkynyl group, C1_6 haloalkyl group, C2_6 haloalkenyl group, C2_6 haloalkynyl group, C2_6 alkylcarbonyl group, C2_6 alkoxycarbonyl group, phenyl group or benzyl group; R5 and R6 represent independently hydrogen atom, halogen atom, C1_6 alkyl group, C3-6 cycloalkyl group, cyano group or phenyl group; and q is an integer of O to 2); n is an integer of O or l; and Ar is phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group which may be substituted or non-substituted (the substituent of the aromatic groups is selected from halogen atom, cyano group, nitro group, .
, .

C1_4 alkyl group, C1_4 haloalkyl group, C1_4 alkoxy group, Cl_4 haloalkoxy group, C1_4 alkylthio group, C1_4 haloalkylthio group, C1_4 alkylsulfonyl group, C1_4 haloalkylsulfonyl group, C2_4 alkoxycarbonyl group, carboxyl group, amino group, C1_4 monoalkylamino group, C2_g dialkylamino group, phenyl group, benzyl group, methylenedioxy group or halomethylenedioxy group, and when the number of the substituents is not less than 2, these substituents may be same or different)), and m is an integer of O to 5 (when it is 2 to 5, the substituents yl may be same or different)], or naphtyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimizyl group, pyrazyl group, quinolyl group, quinoxalyl group, benzofuryl group, benzothienyl group, indolyl group, benzoxazolyl group or benzothiazolyl group which may be substituted or non-substituted ~the substituent of the above aromatic groups is selected from halogen atom, cyano group, nitro group, C1_4 alkyl group, Cl_4 haloalkyl group, C1_4 alkoxy group, C1_4 haloalkoxy group, C1_4 alkylthio group, C1_4 haloalkylthio group, C1_4 alkylsulfonyl group, C1_4 haloalkylsulfonyl group, C2_4 alkoxycarbonyl group, carboxyl group, amino group, C1_4 monoalkylamino group, C2_g dialkylamino group, phenyl group, phenoxy group or benzyl ~ ' ' , .
- , .

- 17 - 203~404 group, and when the number of the substituents is not less than 2, these substituents may be same or different), provided that A is not phenyl group and 3-bromo-4-methoxyphenyl group, when B is phenyl group, are preferred.
Further, (2) compounds of the formula (I) wherein -xl A is ~ (wherein X and I as defined above), and Ylm B is ~ (wherein yl and m are as defined above), provided that A is not phenyl group and 3-bromo-4-methoxyphenyl group, when B is phenyl group), are more preferred.
(3) Compounds of the formula (I) wherein A is naphthyl group furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimizyl group or pyrazyl group which may be substituted or non-substituted (the substituent is the same as defined above), and B is ~ (wherein yl and m are as defined above) are more preferred.

. . .

: . .. , , ; : . .. .

8 ~ Z034404 Also, (4) compounds of the formula (I) wherein A is C1_6 haloalkyl group containing one or more fluorine atoms, halogen atom, cyano group, nitro group, C1_6 alkylthio group, C1_6 alkylsulfinyl group, C1_6 alkylsulfonyl group, C1_6 haloalkylthio group, C1_6 haloalkylsulfinyl group, Cl_6 haloalkylsulfonyl group, C1_6 alkoxy group, C1_6 haloalkoxy group, or C2_6 alkoxycarbonyl group, and B is ~ (wherein y2 is halogen atom, C1-4 alkyl group, Cl_4 alkoxy group, Cl-4 haloalkyl group, Cl-4 haloalkoxy group, Cl-4 alkylthio group, Cl-4 haloalkylthio group, Cl_4 alkylsulfinyl group, Cl_4 haloalkylsufinyl group, Cl-4 alkylsulfonyl group, Cl_4 haloalkylsulfonyl group, sulfonamide group, C2-4 alkenyl group, C2_4 haloalkenyl group, amino group, Cl-4 monoalkylamino group, C2-g dialkylamino group, C2-6 alkoxyalkoxy group, C2_6 alkoxycarbonyl group, cyano , group or nitro group, and r is an integer of 3 to 5 (the substituents y2 may be same or different, and when r = 3 with the substituents at the 2-, 4- and 5-positions, the substituent y2 at the 5-position is not C1-4 alkoxy group, C1-4 haloalkoxy group, C2_6 alkoxyalkoxy group or C2_6 alkoxycarbonyl group), are more preferred.
Furthermore, among the above-mentioned preferred uracil derivatives, .

, .

(i) compounds of the formula (I) wherein R1 and R2 each represents hydrogen atom, zl and z2 each represents oxygen atom, A iS 2-fluorophenyl group, 2-chloropheyl group, 2-chloro-6-fluorophenyl group or 2,6-Ylmdifluorophenyl group, and B is ~ (where yl and m represent the same as defined above); and (ii) compounds of the formula (I) wherein Rl and R2 each represents hydrogen atom, zl and z2 each represents oxygen atom, A is trifluoromethyl group, pentafluoroethyl group or chlorodifluoromethyl group, and B is ~ (wherein y2 and r represent the same as defined above), are still more preferred.
The processes for the preparation of the compounds according to the present invention are described below.
-) As for the method for synthesis of the said uracil derivatives of the present invention, it is possible to synthesize the uracil skeleton by referring to, for example, the synthesis method shown in Comprehensive ~eterocyclic Chemistry, Vol. 3, p. 57, 1984. The preparation processes, including the above method, will be described concretely below.

- 20 - 203~404 (Process A) Step 1 ) R2 ~ C02R7 NH3 or CH3COaNH4 Ra ~ COaR7 m ) Step 2 ) Z' ~ t m ) + B-NCZ~ or B-NHeOR
-' ~IV) ~V) A ~ N- C- N- B

H Zl H H

~VI) ~V~l) Step 3 ) R 2 ~1~
V~l ) + R '--L ~ base , ~ B

A I Z' R' .

- 21 - 2 0 3 44 0 ~

(Process B) Step 1 ) R2 ~ C02R7 acldR2 ~ C02R7 R' X ) ~ X I ) Step 2 ) z~
base ~X I ~ + B-NCZ' or B-NHCOR8 V ~
O
R~ ~ C02R7 R2 R' Z' H A I Z' ~ x ~
(Process C) Step 1 ) , ~
R2 ~, C02R7 11 acid R2 ~_~ C02R7 I + H2NCNH-B ~
A '~ O A '~` N- C- N- B

X ~ ) ~VI) H Z' H

. . . -- ' : . ~. " ' ', :, - 22 - ~ Z 0 3~ ~0 4 Step 2 ) o base ~ ~- B
A I Z' H

(Process D) =:
Step 1 ) O O
N - B CH 3 C 0 2 NH 4~ N - B

~XVI) ~XV) Step 2 ) (X V ) + CZ'C~ 2 base ~ N- B

-`) A H
(~m ~ .
..... .. ~......................................... . .

- - 23 - 2 0 3 ~4 0 4 (Process E) zinc R2 ~ CO2R7 A- CN + BrCHCO2R7 - ) 11 A '~~ NH2 ~XVI~ (X~ ~m~
(Process F) Z' R 2 ~ CN 11 base Il + B-NCZ' or B-NHCOR 8 A '~` NH2 -- ~ X ~ ~ V ~

~ ~ B acid ~ ~ B

A I Z' A I Z' H H
~X~) (Process G) o R 2 ,1~
R2 J~ Z, ~ ' N--B
L2 11 ba se L3 + H2NCNH-B HO `N'~
O H
~xx~ ~xm~ ~xx I ~

.: ' - 24 -- Z03~04 P(O)X' 3 0 0 PX 1 3R 2 ,1~ M ' CN R 2 ,ll~
\r ' N--B ~ ~r N--B
or SOx~ 2 ~ ~N~ ~ `N~
Xl I Z' NC I Z
H H
~xx ~ xxm~
(Process H) O
~XX 1~ ~ + R9SM2 R2~N_B
N
R9S I Z' H
R2,1~ ~XXIV~
peroxide ~ N - B
~` `N~
R9S(O) I Z
H
~XXV~

peroxideR 2~ N - B
--) R9SO2 ¦ Z' ~ X X VI

, , : . -- 25 - 20~4404 (Process I) z2 z2 H ~ halogenating agent R ' ~ N - B
nitrating agent ~ `N~ or thiocyanating ~ ~N~
A I z ~ agent AI Z ' R' R' ~XX~ XX~) (Process J) Step 1 ) z2 Z2 CH3 ~ N-halogen ha ~ CH2 ~
~ N - B succisoimide ~ ' N - B

A I Zl A I Z' R' R' ~XX~ ~XXX~ ,, Step 2 ~
~XXX) + R~ 'Z3-M3 base 3 ~xxx I ~

- . : . . .

R " Z 3 CH 2 ~fi~

J~N~
A I Z' R' X X X 11 ) Step 3 ) z2 HOCH 2 ~
~~ base/water \~ N--B
~XXX) J~N~
A I Z' Rl ~x x x m ) (Process K) z2 z2 R2~N--H base ~N--B
+ x2 _ B
R' R' .) ~XXXIV) ~XXXV) :: ,, ~ ! , ' In the above-shown formulae (in Processes A-K), R1, R2, A, B, zl and z2 are the same as defined above; R7 and R8 represent independently C1_6 alkyl group, benzyl group or phenyl group; R9 represents C1_6 alkyl group or C1_6 haloalkyl group; R10 represents halogen atom, nitro group or thiocyanate group; Rl1 represents C1_4 alkyl group or Cl_4 haloalkyl group; L1 represents halogen atom, methanesulfonate group, p-toluenesulfonate group or favorable elimination group such as C1-4 alkylsulfate group; L2 and L3 represent independently halogen atom, hydroxyl group or C1_4 alkoxy group; xl represents chlorine atom or bromine atom; x2 represents fluorine atom, chlorine atom, bromine atom or iodine atom; M1 represents sodium atom, potassium atom or copper atom; M2 and M3 represent independently sodium atom or potassium atom; Z3 represents oxygen atom or sulfur atom; and hal represents chlorine atom or bromine atom. The compounds of the formulae (VII), (IX), (XIX), (XXI), ~XXII), (XXIII), (XXIV), (XXV), (XXVI), (XXVII), (XXVIII), (XXIX), (XXX), (XXXII) and (XXXIII) are the compounds of the present invention.
Process ~ is a method for synthesizing the compounds of the formula ~I) wherein R2 is hydrogen atom or C1_4 alkyl group. The starting compound of the formula (II) can be synthesized by a known method by referring to, for example, Journal of Heterocyclic Chemistry, Vol. 9, ', : .. : ~ ~ , ' :

- 28 - Z0~440~

p.513, 1972. In Step 1, the compound of the formula (II) is reacted with ammonia or ammonium acetate in a solvent such as ethanol in the presence of acetic acid, thereby obtaining a compound of the formula (III) in a high yield.
In Step 2, the obtained compound of the formula (III) and an iso(thio)cyanate of the formula (IV) or a (thio)carbamic acid ester of the formula (V) are reacted in an inert solvent in the presence of a base, thereby obtaining a compound of the formula (VII) (a compound of the present invention) without isolating the intermediate (VI). The bases usable in the above reaction include alkali metal alkoxides such as sodium ethoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; and sodium hydride.
As the solvent, there can be used lower alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane; halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane; amides such as dimethylformamide and dimethylacetamide; acetonitrile;
dimethyl sulfoxide and mixtures thereof. Generally, it is preferred to use sodium alkoxide (R70Na) as base in an alcohol (R70H) solvent which is the same as R7 in the - 29 - 20~4404 formula (III), or to use sodium hydride as base in such solvent as tetrahydrofuran, dimethylformamide or dimethyl sulfoxide. The reaction temperature is in the range from -30C to the reflux temperature of the reaction mixture.
In Step 3, the compound of the formula (VII) and a compound of the formula (VIII) are reacted in an inert solvent in the presence of a base to form a compound of the formula (IX) of the present invention. When R1 is Cl_4 alkyl group, C2_4 alkenyl group, C2_4 alkynyl group or C2_4 alkoxyalkyl group, it is preferred to use a halide such as chloride and bromide as R1-L1 of the formula (VIII). When R1 is C1_4 alkyl group, use of dialkyl sulfate (R12So4) is also favorable. Preferred examples of the base used in the above reaction are alkali metal alkoxides such as sodium ethoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; and sodium hydride. As the solvent, it is preferred to use water; lower alcohols such as ethanol;
ethers such as 1,2-dimethoxyethane and tetrahydrofuran;
dimethylformamide; and dimethyl sulfoxide.
The reaction temperature usable is from 0C to the reflux temperature of the reaction mixture, preferably 0 to 30C. When Rl is formyl, a halide of formic acid is preferably used as R1-L1, and When Rl is C2_6 alkylcarbonyl group, a halide or anhydride of C2-6 alkanic acid is preferably used as Rl-Ll. When R1 is C2_6 - 30 - z034404 alkoxycarbonyl group, C2_6 alkyl chloroformate or bromoformate is preferably used as R1-L1. In the above reaction, sodium hydride is preferably used as base.
However, in case of introducing C2_6 alkylcarbonyl group by using an acid anhydride, the reaction can be carried out without using any base. Dimethylformamide or dimethyl sulfoxide is preferably used as solvent.
Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture, preferably 0 to 30C.
When zl in the compound of the formula (VII) is sulfur atom, alkylation of the compound usually produces a mixture of N- and S-alkylation products. The desired N-C1_4 alkyl, N-C2_4 alkenyl, N-C2_4 alkynyl or N-C2_4 alkoxyalkyl compound can be easily isolated from the said mixture by an ordinary method such as column chromatography.
Process B is a method wherein various kinds of substituent other than hydrogen atom, can be introduced as Rl before forming the uracil ring. In Step 1, a compound of the formula (II) and an amine of the formula ~X) are reacted in the presence of an acid catalyst to form a compound of the formula (XI~. Acetic acid or trifluoroacetic acid is preferably used as acid catalyst in this reaction.

, :

- 3i - 203~04 In Step 2, a compound of the formula (XI) and an iso(thio)cyanate of the formula (IV) or a (thio)carbamic acid ester of the formula (V) are reacted in the presence of a base, thereby obtaining a compound of the formula ~IX) of the present invention without isolating the intermediate of the formula (XII). The reaction conditions such as the kind of base, kind of solvent and reaction temperature used in this step are substantially the same as those used in Step 2 of Process A.
Process C is another method for synthesizing the intermediate (VI) in Step 2 of Process A. In Step 1, a compound of the formula (II) and a (thio)urea of the formula (XIII) are reacted in an inert solvent in the presence of an acid catalyst to form a compound of the formula (VI). In this reaction, strong mineral acids such as sulfuric acid and hydrochloric acid, organic acids such as p-toluenesulfonic acid and phosphoric acids such as orthophosphoric acid and polyphosphoric acid are preferably used as acid catalyst. As the solvent, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as carbon tetrachloride and chlorobenzene and ethers such as 1,2-dsimethoxyethane and 1,9-dioxane are preferably used. Reaction temperature is in the range from 20C to the reflux temperature of the reaction mixture, and it is preferred to carry out the ' ~ `

, - 32 - 2V3~4~4 reaction at the reflux temperature of the reaction mixture.
In Step 2, the compound of the formula (VI) is subjected to a cyclization reaction in an inert solvent in the presence of a base to form a compound of the formula (VII) which is a compound of the present invention. The reaction conditions, i.e. the kind of base, the kind of solvent used and reaction temperature used in this step are substantially the same as employed in Step 2 of Process A.
Process D is a method for synthesizing the compounds of the present invention represented by the formula (I) wherein zl is sulfur atom. The starting compound of the formula (XIV) can be synthesized by a conventional method. In Step 1, similarly to Step 1 of Process A, a compound of the formula (XIV) is reacted with ammonium acetate in an inert solvent such as ethanol in the ,_~
presence of acetic acid to form a compound of the formula (XV) .
In Step 2, the compound of the formula (XV) is reacted with phosgene or thiophosgene in an inert solvent in the presence of a base to obtain a compound of the formula (VII~ of the present invention. The base used in this reaction is preferably an organic base such as triethylamine and pyridine. As the solvent, aromatic hydrocarbons such as benzene and toluene and halogenated _ 33 _- 2 0 3 4 4 0 4 hydrocarbons such as dichloromethane and 1,2-dichloroethane are preferably used. Reaction temperature is in the range from 0C to reflux temperature of the reaction mixture, preferably 0 to 30C. In the above reaction, l,l'-thiocarbonyldiimidazole can be used in place of thiophosgene.
Process E is another method for synthesizing the intermediate (III) in Step 1 of Process A. This process comprises reacting a nitrile of the formula (XVI) with an alpha-bromoacetic ester of the formula (XVII) in an inert solvent in the presence of zinc to obtain a compound of the formula (III). The solvent used in this reaction is preferably selected from aromatic hydrocarbons such as benzene and toluene and ethers such as diethyl ether, tetrahydrofuran, l,2-dimethoxyethane and 1,4-dioxane.
Reaction temperature is in the range from 20C to the reflux temperature of the reaction mixture, and it is preferred to carry out the reaction at the reflux temperature of the reaction mixture.
Process F is a method for synthesizing the compounds of the present invention represented by the formula (I) wherein z2 is imino group or oxygen atom. The starting compound of the formula (XVIII) can be synthesized by a known method. This starting compound (XVIII) is reacted with a compound of the formula (IV) or (V) in an inert solvent in the presence of a base to obtain a compound of .. ... . . : . , , :
.

20;~404 the formula (XIX) of the present invention. The reaction conditions such as kinds of base and solvent, and reaction temperature are substantially the same as used in Step 2 of Process A. By hydrolysis of the compound of the formula (XIX) under an acidic condition a compound of the formula (VII) of the present invention is obtained.
The acid used in this hydrolysis reaction is preferably a mineral acid such as hydrochloric acid, sulfuric acid and nitric acid, more preferably a diluted aqueous solution thereof. Reaction temperature is in the range from 20C
to the reflux temperature of the reaction mixture, and it is preferred to perform the reaction at the reflux temperature of the reaction mixture.
Process G is a method for synthesizing the compounds of the present invention of the formula (I) wherein A is halogen atom or cyano group. A malonic acid derivative of the formula (XX) and a (thio)urea of the formula (XIII) are reacted in an inert solvent in the presence of a base to form a compound of the formula (XXI). The bases usable in the above reaction include metal alkoxides such as sodium ethoxide, alkali methal hydroxides such as sodium hydroxide, alkali metal carbonates such as potassium carbonate, and sodium hydride. As the solvent, there can be used lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as - 35 - 203~404 diethyl ether, tetrahydrofuran and 1,~-dioxane, dimethylformamide and the like. Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture. When both of L2 and L3 in the compound of the formula (XX) are halogen atom, it is possible to obtain the compound of the formula (XXI) by conducting the reaction in a solvent such as dioxane without adding a base at a temperature in the range from 0C to the reflux temperature of the reaction mixture.
The compound of the formula (XXI) is reacted with phosphorus oxyhalide, phosphorus trihalide or thionyl halide to form a compound of the formula (XXII). In some cases, presence of a base facilitates the progress of the reaction. Examples of the said phosphorus oxyhalide are phosphorus oxychloride and phosphorus oxybromide.
Examples of phosphorus trihalide are phosphorus trichloride and phosphorus tribromide, and examples of thionyl halide are thionyl chloride and thionyl bromide.
The base used in the above reaction is preferably an organic base such as pyridine and triethylamine.
The compound of the formula (XXII) is reacted with a metallic cyanide in an inert solvent to form a compound of the formula (XXIII~. Preferred examples of metallic cyanide used in the above reaction are sodium cyanide, potassium cyanide and copper cyanide. As the solvent, there can be used lower alcohols such as methanol and ,:, ~ - . ~ . . , : . ~ . , :

`
- :, ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane, dimethylformamide and the like.
Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture.
Process H is a method for synthesizing the compounds of the formula (I) wherein A is alkylthio group, alkylsulfinyl group or alkylsulfonyl group. A compound of the formula (XXII) and a metal salt of alkylmercaptan are reacted in an inert solvent to form a compound of the formula ~XXIV). As the typical examples of metal in the metal salts of alkylmercaptan, sodium and potassium may be exemplified. As the solvent, ethers such as 1,2-dimethoxyethane and tetrahydrofuran are preferably used.
Also, excess mercaptan can be used as solvent. Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture.
The compound of the formula (XXIV) is reacted with an equimolar amount of a peroxide in an inert solvent to obtain a compound of the formula (XXV), and the obtained compound of the formula (XXV) is further reacted with an equimolar amount of a peroxide to obtain a compound of the formula (XXVI). Also, by reacting the compound of the formula (XXIV) with twice as much molar amount of a peroxide, it is possible to obtain the compound of the formula (XXVI) without isolating the compound of the '.

formula (XXV) As peroxide, there can be used hydrogen peroxide, peracetic acid, m-chloroperoxy benzoic acid and the like. As the solvent, there can be used alcohols such as methanol and ethanol, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, water, acetic acid and the like. Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture, preferably 0 to 30C.

Process I is a method for synthesizing a compound of the formula (XXVIII) of the present invention by converting hydrogen atom in an uracil derivative of the formula ~XXVII) wherein R2 is hydrogen atom, into halogen atom,m nitro group or thiocyanate group. As the halogenating agent used in this process, chlorine, sulfuryl chloride or N-chloroxuccinimide is preferably used for chlorination; bromine, sulfuryl bromide or N-bromosuccinimide for bromination; and iodine or iodine monochloride for iodination. As the solvent, acetic acid or halogenated hydrocarbons such as dichloromethane and carbon tetrachloride are preferably used. Reaction temperature is ln the range from 0C to the reflux temperature of the reaction mixture, preferably 20C to the reflux temperature.
As the nitrating agent, nitric acid or a mixture of nitric acid and sulfuric acid is preferably used. As the .

~ 38 - 203440~

solvent, it is preferred to use halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane or acetic acid. Solvent may not necessarily be used. Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture, preferably 0 to 50C.
The thiocyanating agent used in the above process is -~ preferably the one which is capable of generating thiocyanogen by using ammonium thiocyanate and bromine.
As the solvent, halogenated hydrocarbons such as dichloromethane and carbon tetrachloride, ethers such as 1,2-dimethoxyethane and tetrahydrofuran, and acetic acid may be used. Reaction temperature is in the range from 0C to 50C, preferably 0 to 30C.
Process ~ is a method for synthesizing a compound of the formula (XXX) of the present invention by converting methyl group in an uracil derivative of the formula ? (XXIX) wherein R2 is methyl group, into halomethyl group, and further synthesizing a compound of the formula (XXXII) or a compound of the formula (XXXIII) of the present invention by converting halomethyl group in the compound of the formula (XXX) into alkoxymethyl group, alkylthiomethyl group or hydroxymethyl group.
In Step 1, a compound of the formula (XXIX) is reacted with N-chlorosuccinimide or N-bromosuccinimide to obtain a 5-chloromethyl or 5-bromomethyl compound of the .~ .

_ 39 _- 2 03 4 ~ o 4 formula (XXX). As the solvent, halogenated hydrocarbons such as carbon tetrachloride are preferably used.
Reaction temperature is in the range from 50C to the reflux temperature of the reaction mixture, and the reflux temperature of the reaction mixture is preferred.
This reaction is accelerated by adding a radical initiator such as benzoyl peroxide or azobisisobutyronitrile, or by UV irradiation.
In Step 2, 5-halomethyl compound of the formula (XXX) is reacted with an alkali metal alkoxide or thioalkoxide of the formula (XXXI) to form a 5-alkoxymethyl or 5-alkylthiomethyl compound of the formula (XXXII). The alkali metal alkoxide or thioalkoxide of the formula (XXXI) used in the above reaction can be easily synthesized by reacting an alcohol or mercaptan with an alkali metal. Ethers such as 1,2-dimethoxyethane and tetrahydrofuran can be preferably used as solvent in the above reaction. Also, excess alcohol or mercaptan can be used as solvent. Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture, preferably 20 to 70C.
In Step 3, 5-halomethyl compound of the formula (XXX) is hydrolyzed in the presence of a base to obtain a 5-hydroxymethyl compound of the formula (XXXIII). As the base used in the hydrolysis, alkali metal carbonates such as sodium carbonate or alkali metal hydrogencarbonates such as sodium hydrogencarbonate may be used. Reaction temperature is in the range from 0C to the reflux temperature of the reaction mixture, preferably O to 30C.
Process K is a method of reacting an uracil compound of the formula (XXXIV) having hydrogen atom at the 3-position and a compound of the formula (XXXV) in an inert solvent in the presence of a base to obtain a compound of the formula (I). The halogenated aromatic compounds having electron withdrawing groups can be used as the compound of the formula (XXXV). The halogen may be fluorine, chlorine, bromine or iodine atom. As the base used in the above reaction alkali metal alkoxides such as sodium ethoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and sodium hydride may be used. As the , solvent, there can be used lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethyl sulfoxide and mixtures thereof. Generally, it is preferred to use sodium hydrlde as base and tetrahydrofuran, - 4i - ~3~04 dimethylformamide or dimethyl sulfoxide as solvent.
Reaction temperature is in the range from -30C to the reflux temperature of the reaction mixture.
In the above-described processes (Process A -Process K), no specific definition is given to molar ratio of the reactants, but usually it is advantageous to carry out the reactions by using the reactants at equimolar ratio or about equimolar ratio.
When it is necessary to purify the compounds of the present invention, such can be carried out by the suitable separating and purifying methods such as recrystallization and column chromatography.
Among the compounds of the present invention, those having asymmetric carbon atoms include the optically active compounds of both (+) and (-) forms.
Further, in case there exist the isomers of steric configuration in the compounds of the present invention, they include both cis and trans isomers.
Examples of the compounds included in the scope of the present invention are shown in Tables 1 to 5. It is to be understood that the compounds shown in these tables are illustrative ones and don't define the compounds provlded by the present invention.
In Tables 1 to 5, Ql to Q61 denote the groups represented by the following formulae:

- ~I 2 - - 2~34404 ~4 ~ ~14 ~ 5 N~D 5 N~/s ~ 43 ~ 203~404 2N~ ~ 5 2 ~ , ,~

3Nl~o~ /~ 5 2 U~

2NI~ ~ 4 a ,~, Q 25 Q 26 Q 27 3 N~

~ i - !
~ . . ' .

- 44 - 203~404 N~ ,~ 5 3NIr N'~J~ 3N~

N` o ~ S ' N~o ~ sN~--N~ N~ ~ 5 3 U~S~ 6 ~ 6 ~

~ ~ ~ 6 ~ : ~ ~

- . ' ' ; ' ,' ~, ': ' ' .. . .. . .
.
.
, -.
,. ': , . i' ' S ~N0'`~ 6 [~J 2 ~NO\J 2 ,3 ~ 1~0~

6 ~ 8~ N

, , D~ ~ ~

': ~
-, .

2034~ )4 30~ 4 ~CJ~ ~ ~ !
2 ~ o 2 ~ ~

- , , : ' '' ' . . .

- . .

- 47 - 203~1~04 In use of the compounds of the present invention as an active ingredient of pesticides, they may be mixed with a suitable carrier or diluent selected from either solid carriers such as clay, talc, bentonite and diatomaceous earth or liquid carriers including water, alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene, toluene and xylene, chlorinated hydrocarbons, ethers, ketones, esters such as ethyl acetate, and acid amides such as dimethylformamide.
Also, if necessary, they may be further added with a suitable adjuvant or adjuvants such as emulsifier, dispersant, suspension agent, penetrating agent, spreader, stabilizer, etc., and can be offered to practical use in various forms of formulatipn such as emulsifiable concentrate, oil solution, wettable powder, dust, granules, flowable, etc.
Also, the compounds of the present invention may be mixed with other herbicides, insecticides, fungicides, plant-growth regulating agent, synergists, etc., during formulation and application thereof, as occasion demands.
The dosage (drug-concentration) of the compounds of the present invention varies depending on the place of application, time (seasons) of application, method of application, diseases or insect pests to be applied, crops to be treated and other factors, but generally it is appropriate to apply the compound at a rate of about .. . ......................................... .
.. . . . . . .... . .

- 48 - 203~404 0.005 ~ 50 kg/ha calculated as the amount of active ingredient.
In the pesticides of the present invention, an amount of the active ingredient is 0.01 to 70 wt%.
Concretely, the formulations and kinds of preparations thereof are set forth below.

f-j Active Surfac- Other ,,! ingredient Carrier tant components (adjuvants) (wt%) (wt%)(wt%) (wt%) Emulsifiable concentrates 1 ~ 25 52 ~ 95 3 ~ 20 0 ~ 20 Oil solutions 1 ~ 30 57 ~ 99 Flowables 1 ~ 70 10 ~ 901 ~ 20 0 ~ 10 Wettable powders 1 ~ 70 15 ~ 933 ~ 10 0 ~ 5 Dusts 0.01 ~ 30 67 ~ 99.5 0 ~ 3 Granules 0.01 ~ 30 67 ~ 99.5 0.8 ,,~

In application, emulsifiable concentrates, oil solutions, flowables and wettable powder are diluted with a predetermined amount of water and applied. Dusts and granules are directly applied without being diluted with water.
Each component of the above formulations is exemplified as follows.

_ 49 - 203~404 Emulsifiable concentrates Active ingredient: a compound of the present invention Carrier: xylene, dimethylformamide, methylnaphthalene, cyclohexanone, dichlorobenzene or isophorone Surfactant: Sorpol 2680, Sorpol 3005X or Sorpol 3353 Other components: piperonyl butoxide and/or benzotriazole Oil solutions Active ingredient: a compound of the present invention Carrier: xylene, methylcellosolve or kerosense Fl~wables Active ingredient: a compound of the present invention `) Carrier: water Surfactant: Lunox 10000C, Sorpol 3353, Soprophor FL, Nippol, ~grisol S-710 or sodium ligninesulfonate Other components: Xanthan gum, formalin, ethylene glyxol and/or propylene glycol ~ettable E~owders Active ingredient: a compound of the present invention - 50 - 203~404 Carrier: calcium carbonate, kaolinite, Zeeklike D, Zeeklite PFP, diamtomaceous earth or talc Surfactant: Sorpol 5039, Lunox 1000C, calcium ligninesulfonate, sodium dodecylbenzene-sulfonate, Sorpol 5050, Sorpol 005D or Sorpol 5029-0 Other components: Carplex #80 Dusts Active ingredient: a compound of the present invention Carrier: calcium carbonate, kaolinite, Zeeklite D or talc Other components: diisopropyl phosphate and/or Carplex #80 Granu,les (1) Active ingredient: a compound of the present .~ invention Carrier: calcium carbonate, kaolinite, bentonite or talc Other components: calcium ligninesulfonate and/or polyvinyl alcohol Granules ~1 Active ingredinent: a compound of the present invention ~ .

,, . :
:.
:
, .
.

- 51 - 203440~

Carrier: wheat flour, wheat bran, corn grits or Zeeklite D
Other components: paraffin and/or soybean oil The compounds of the present invention are effective, with very low drug-concentration, on various kinds of insect pests; e.g., agricultural insect pests such as green rice leaf hopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), green peach aphid (~y~ persicae), twenty eight-spotted lady beetle (Henosepilachna viaintioctopunctata), diamondback moth (Plutella ~ylostella), common cutworm (Spodoptera litura) and ; Tetranychidae such two-spotted spider mite (Tetranychus urticae), citrus red mite (Panonychus citri) and Kanzawa spider mite (Tetxanychus kanzawai); sanitary insect pests such as house mosquito (Culex E~E~ens palens), housefly (~usca domestics), ant (Formicidae) and `~ lice (Anoplura); stored product insect pests such as maize weevil (Sitophilus oryzae), red flour beetle (Tribolium castaneum) and almond moth (Cadra cautella);
house insect pests such as termites; and verterinary insect pests such as acarids, fleas and lice.
In other words the compounds of the present invention can effectively control and prevent Dictyoptera, Isoptera, Hemiptera, Lepidoptera, Coleoptera, ~ymenoptera, Dipt-ra, ticks, acarl and lice.

.. ' ~ .

-- 52 - 2034~04 Further, some of the compounds of the present invention have a high herbicidal activity against various weeds, for example, those posing serious problems on farming, such as Abutilon avicennae, Xanthium strumarium, Amaranthus retroflexus, Echinochloa, Diaitaria adscendes, Setaria viridis, Sorahum bicolor, etc. at a notably low drug-concentration and they cause no harm to the important crops such as rice, corn, wheat, soybean, cotton, beet, etc.

EXAMP~ES
In the following, the processes for synthesizing the compounds of the present invention will be illustrated by the examples concretely. It is to be understood, however,that these examples are merely intended to be illustrative and not to be construed as limiting the scope of the invention.

Synthesis Example 1 3-(2-fluoro-g-chlorophenyl)-6-(2-fluorophenyl)-2,4(lH,3~L- yrimidinedione (compound No. 1.3 Qf the present invention) 52.5 g of ethyl~2-fluorobenzoyl~ acetate and 96.3 g of ammonium acetate were added to 250 ml of ethanol, followed by dropwise addition of 75.0 g of acetic acid to the solution with stirring at 10C. The resulting solution was heated to room temperature and then stirred , - 53 ~ X03~404 under reflux for 4 hours. After the reaction was completed, the solvent was distilled away under reduced pressure and the residue was dissolved in diethyl ether.
This ether solution was washed with dilute hydrochloric acid, water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate.
The solvent was distilled away to obtain 50.5 g of ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate.
2.1 g of this ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate was added dropwise to a solution of 0.5 g of sodium hydride ~purity: 55%) in 20 ml of dimethylformamide with stirring at 0C. The resulting solution was further stirred at room temperature for 15 minutes and then cooled to -30C and added dropwise with 20 ml of a toluene solution of 1.7 g of 2-fluoro-4-chlorophenyl isocyanate. The resultant solution was heated to room temperature and stirred at 80C for 30 minutes. Then the solvent was distilled away under reduced pressure and lO0 ml of water was added to the residue to dissolve it. This aqueous solution was washed twice with diethyl ether and added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid.
The precipitated crystals were filtered out and dried under the reduced pressure to obtain 3.0 g of a crude product. This crude product was washed with heated - 54 - 2~4~

diisopropyl ether and then dried to obtain 2.4 g of the objective compound.
M.p.: 186.0 - 190.0C.
H-NMR (DMSO d-6, TMS, ~ ppm): 6.05 (lH,s), 7.10 - 8.05 (7H,m), 11.77 (lH,bs) Synthesis Example 2 3-t4-trifluoromethoxyphenyl)-6-(2-chlorophenyl)-2 4-(lH,3H)-pyrimidinedione (compound No. 1.14 of the present inventiQn) 2.0 g of sodium hydride (purity: 55%) was added to 100 ml of dimethylformamide, followed by dropwise addition of 7.9 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate to the solution with stirring at 0C. The resulting solution was stirred at room temperature for 15 minutes and added with 8.7 g of ethyl 4-trifluoromethoxyphenylcarbamate. The solution was further stirred at 100C for 4 hours. Then the solvent was distilled away under reduced pressure and the residue was dissolved in 200 ml of water and washed twice with diethyl ether. This aqueous solution was added to a mixed solution of 100 g of ice and 50 ml of concentrated hydrochloric acid. The precipitated crystals were filtered out and dried under reduced pressure to obtain 10.7 g of a crude product. This crude product was washed with heated diisopropyl ether and dried to obtain 9.7 g of the objective compound.

~' ' ,: .:

2034~)4 M.p.: 254.0 ~ 256.0C.
H-NMR (CDCl3 + DMSO d-6, TMS, ~ ppm): 5.67 (lH,s), 7.20 ~ 7.35 (8H,m), 11.60 (lH,bs) Synthesis Example 3 1-ethoxymethyl-3-(4-trifluoromethoxyphenyl)-6-(2-chlorophenyl)-2r4(lH.3H)-pyrimidinedione (compound No.
1.41 of the present invention) 0.5 g of sodium hydride (purity: 55%) was added to 50 ml of dimethylformamide, and then 3.8 g of 3-(4-trifluoromethoxyphenyl)-6-(2-chlorophenyl)-2,4(lH,3H)-pyrimidinedione was added to the solution with stirring at 0C. The resulting solution was stirred at room temperature for 15 minutes, then added dropwise with 1.3 g of chloromethylethyl ether and further stirred at room temperature for 3 hours. The reaction mixture was added into 200 ml of ice water and extracted with 200 ml of ethyl acetate. The organic layer was washed with water and dried, and then the solvent was distilled away under reduced pressure to obtain 3.8 g of a crude product.
This crude product was recrystallized from diisopropyl ether to obtain 3.2 g of the objective compound.
M.p.: 168.5 ~ 172.0C.
H-NMR (CDCl3, TMS, ~ ppm): 1.07 (3H,t,J=6.0 Hz), 3.38 (2H,q,J=6.0 Hz), 4.59 ~lH,d,J=10.0 Hz), 5.26 (lH,d,J=10.0 Hz), 5.70 (lH,s), 7.20 ~ 7.45 (8H,m) -Synthesis Example 4 3~(4-trifluoromethoxyphenyl)-5-bromo-6-(2-chlorophenyl)-2,4(lH 3H)-pyrimidinedione (compound No. 1.33 of the present invention) 3.8 g of 3-(4-trifluoromethoxyphenyl)-6-(2-chlorophenyl)-2,4(lH,3H)-pyrimidinedione was added to 75 ml of acetic acid, followed by dropwise addition of 1.7 g of bromine to the solution with stirring at room temperature. The reaction mixture was further stirred for 2 hours and then the solvent was distilled away under reduced pressure. The residue was dissolved in 200 ml of ethyl acetate, washed with an aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous sodium sulfate. Then the solvent was distilled away to obtain 4.5 g of a crude product. This crude crystal product was washed with heated diisopropyl ether and dried to obtain 4.1 g of the objective compound.

M.p.: 264.0 ~ 268.5C.
H-NMR (CDC13 + DMSO d-6, TMS, ~ ppm): 7.35 ~ 7.60 (8H,m) Synthesis Example 5 3-(4-chLoxophenyl)-6-(2-chlorophenyl)-(lH,3H)-pyri~1d~ne-2-thir~D-4-one (compound No. 1.93 of the present inventio~
2.3 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate was added dropwise to a solution of 0.5 g of ~' :

`

- 57 - 2~34404 sodium hydride (purity: 55%) in 20 ml of dimethylformamide with stirring at 0C. The mixed solution was stirred at room temperature for 15 minutes, then cooled to 0C and added with 1.7 g of 4-chlorophenyl isothiocyanate. The resulting solution was heated to room temperature and further stirred at 100C for one hour. Then the solvent was distilled away under reduced pressure and the residue was dissolved by adding 100 ml of water. This aqueous solution was washed twice with diethyl ether and added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid. The aqueous mixture was extracted with 100 ml of ethyl acetate, washed with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away to obtain 2.1 g of a crude product. This crude product was washed with heated diisopropyl ether and dried to obtain 1.0 g of the objective compound.
M.p.: 245.0 ~ 250.5C.
H-NMR (CDCl3 + DMSO d-6, TMS, ~ ppm): 5.94 (lH,s), 7.20 ~ 7.55 (8H,m) SYD~h~ Ysmple 6 3-(3,4-dic~lo~ophunyl)-6-(2,6-difluorophe~yl)-2,4(1H,3H)-pyrim~ ne (compound,,,~Q. 1.166 of the present inve~Qn~

3.0 g of ethyl a-bromoacetate and a trace amount of iodine were added to a solution of 18.3 g of zinc in 250 ml of tetrahydrofuran under reflux and vigorously stirred to start the reaction. The reaction solution was cooled to room temperature and added with a 30 ml tetrahydro-furan solution of 13.9 g of 2,6-difluorobenzonitrile at one time. Then 17.8 g of ethyl a-bromoacetate was added dropwise at such a rate that slow refluxing would continue. The reaction solution was further refluxed for one hour, cooled, added into 350 ml of an aqueous solution of 50.0 g of ammonium chloride and extracted with 300 ml of diethyl ether. The obtained organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 16.5 g of ethyl 3-amino-3-(2,6-difluorophenyl)-2-propenoate.
1.12 g of the thus obtained substance was added dropwise to a solution of 0.24 g of sodium hydride (purity: 55~) in 20 ml of 1,4-dioxane with stirring at 0C. The resulting solution was stirred at room temperature for one hour, cooled to 0C and added with 0.95 g of 3,4-dichlorophenyl isocyanate. After stirring at room temperature for 8 hours, the reaction solution was concentrated under reduced pressure and dissolved with 100 ml of water. After washing the solution with diethyl ether, an aqueous layer was added into a mixed , ~ , -: . . . , : -~'"'' . . ' ' . ,:

solution of 20 ml of concentrated hydrochloric acid and 50 g of ice. The aqueous mixture was extracted with 100 ml of ethyl acetate, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain a crude product.
This crude product was recrystallized from a mixed solvent of diisopropyl ether and isopropyl alcohol to obtain 0.20 g of the objective compound.
M.p.: 255.5 ~ 256.5C.
H-NMR (CDCl3 + DMSO d-6, TMS, ~ ppm): 5.78 (lH,s), 6.90 ~ 7.75 (6H,m), 8.55 ~lH,bs) Synthesis Example 7 3- r4- ~ hloro-5-trifluoromethyl-2-pyridyloxy)phenyll-6-~2-chlorophenyl)-2,4(1H 3H)-pyrimidinedione (compound No.
1.66 of the pX~sent invention) 8.7 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate was added dropwise to a qo ml dimethylformamide of 1.8 g of sodium hydride (purity: 55%) with stirring at 0C. The solu-tion was stirred at room temperature for 15 minutes, cooled to 0C and added dropwise with a 20 ml dimethylformamide solution of 7.2 g of ethyl q-methoxymethoxyphenylcarbamate.
After stirring the solution at 120C for 2 hours, the solvent was distllled away under reduced pressure. The residue was dissolved with 200 ml of water and washed with diethyl ether.
The obtained aqueous layer was added into a mixed solution of ,, .

., 50 ml of concentrated hydrochloric acid and 150 g of ice.
The precipitated crystals were filtered out and dried under reduced pressure to obtain 10.0 g of 3~(4-methoxymethoxy-phenyl)-6-(2-chlorophenyl)-2,4(lH,3H)-pyrimidinedione.
7.0 g of the obtained 3-(4-methoxymethoxyphenyl)-6-(2-chlorophenyl)-2,4(lH,3H)-pyrimidinedione was dissolved in 100 ml of tetrahydrofuran and then added dropwise with 10 ml of concentrated hydrochloric acid with stirring at room temperature. The mixed solution was further stirred at room temperature for 12 hours and extracted with 200 ml of ethyl acetate. The organic layer was washed with a sodium chlorlde aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 4.5 g of 3-(4-hydroxyphenyl)-6-(2-chlorophenyl)-2,4(lH,3H)~
pyrimidinedione.
1.1 g of the obtained 3-(4-hydroxyphenyl)-6-(2-chlorophenyl)-2,4(lH,3H)-pyrimidinedione was added to a 10 ml dimethylformamide solution of 0.10 g of sodium hydride (pur~ty: 55%) with stirring at room temperature.
The mixed solution was stirred at room temperature for 15 minutes, added with 0.7 g of 2,3-dichloro-5-trifluoromethylpyridine, further stirred t 100C for 2 hours. The reaction mixture was added to lO0 ml of water and extracted with 100 ml of ethyl acetate. The organic layer was washed with a sodium chloride aqueous solution - . . .

~ .
~ .

- 61 - 203~04 and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 0.8 g of the objective compound.
M.p.: 175.0 ~ 176.0C.
H-NMR (DMSO d-6, TMS, ~ ppm): 5.70 (lH,s), 7.32 ~4H,s), 7.49 (4H,s), 7.49 (4H,s), 8.20 ~ 8.60 (3H,m) Synthesis Example 8 3-(4-trifluoromethoxyphenyl)-5-fluoro-6-phenyl-2 4(lH,3H)-pyrimidinedione (compound No. 2.56 of the present invention) 6.0 g of ethyl a-fluorobenzoylacetate and 7.0 g of ammonium acetate were added to 50 ml of ethanol, followed by dropwise addition of 6.0 g of acetic acid to this solution with stirring at room temperature. The mixed solution was further stirred under reflux for 4 hours and added to a cooled aqueous solution of sodium hydrogencarbonte. This aqueous mixture was extracted with 200 ml of diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 5.5 g of ethyl 2-fluoro-3-amino-3-phenyl-2-propenoate.
1.00 g of the thus obtained substance was added dropwise to a solution of 0.24 g of sodium hydride (purity: 55%) in 20 ml of dimethylformamide with stirring at 0C. After stirring at room temperature for 15 .
' - 62 - 203~404 minutes, the solution was cooled to 0C and added dropwise with 1.02 g of 4-trifluoromethoxyphenyl isocyanate. The mixed solution was heated to room temperature and further stirred at 80C for 2 hours.
Then the reaction solution was concentrated under reduced pressure and dissolved in 100 ml of water. The resulting aqueous mixture was washed with diethyl ether and the obtained aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice.
The precipitated crystals were filtered out and dried under reduced pressure to obtain a crude product. The obtained product was washed with heated diisopropyl ether and dried to obtain 0.57 g of the objective compound.

M.p.: 295.0 ~ 303.0C.
H-NMR (CDC13 + DMSO d-6, TMS, ~ ppm): 7.32 (4H,s), 7.45 ~ 7.85 (5H,m) Synthesi$ ~xample 9 3-(4-trifluQI~m~hoxyphenyl)-5-iodo-6-phenyl-2 4(1H,3H)-pyrimidinedione (compound No. 2 ! 7 o._ the present invention) 0.45 g of 3-(4-trifluromethoxyphenyl-6-phenyl-2,4~lH,3H)-pyrimidinedione was added to 20 ml of chloroform, and to this solution was added dropwise 0.5 ml of iodine monochloride with stirring at room temperature. The mixed solution was further stirred at room temperature for one hour and then poured into ice -:: ' ' ~ ' .; ,; ,, ~
i water. This aqueous mixture was extracted with 50 ml of chloroform and the obtained organic layer was washed with a sodium thiosulfate aqueous solution and a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 0.53 g of a crude product ~crystals). These crystals were washed with heated diisopropyl ether and dried to obtain 0.40 g of the objective compound.

M.p.: 294.0 ~ 298.0C.
H-NMR (CDCl3, TMS, ~ ppm): 7.30 (5H,s), 7.50 (4H,s), 9.65 (lH,bs) Synthesis Example 10 1-methyl-3-(2-fluoro-4-chlorophenyl)-6-(3-trifluoromethylphenyl)-2 4(lH,3H)-pyrimidinedione ~compound No. 2.57 of the present invention) 1.00 g of 3-(2-fluoro-4-chlorophenyl)-6-(3-trifluoromethylphenyl)-2,4(1H,3H)-pyrimidinedione was dissolved in 10 ml of dimethylformamide, followed by addition of 0.48 g of anhydrous potassium carbonate and 0.48 g of methyl iodide, and stirring of the solution at room temperature for 4 hours. The resulting reaction solution was poured into water and the precipitated crystals were filtered out and dried to obtain 0.90 g of the objective compound.
M.p.: 139.0 ~ 142.0C.

- 69 - 203440~

H-NMR (DMSO d-6, TMS, ~ ppm): 3.20 (3H,s), 5.85 (lH,s), 7.12 - 7.40 ~3H,m), 7.49 ~ 7.86 (4H,m) Synthesis Example 11 3-(4-trifluoromethoxyphenyl)-5-cyano-6-phenyl-2.4(lH 3H)-pyrimidinedione (compound No. 2.5 of the present invention) 0.7 g of 3-(4-triluoromethoxyphenyl)-5-bromo-6-(2-chlorophenyl)-2,4(lH,3H)-pyrimidinedione and 0.6 g of cuprous cyanide were added to 30 ml of N-methyl-pyrrolidone and stirred at 200C for 8 hours. After cooling, the solution was added to 100 ml of water and extracted with 100 ml of ethyl acetate. The obtained organic layer was washed thrice with water and dried over anhydrous sodium sulfate.
Then the solvent was distilled away under reduced pressure to obtain 0.62 g of a crude product. This crude product was purified by preparative thin-layer chromatography (developing solvent: a mixed solvent of chloroform and ethyl acetate) to obtain 0.20 g of the objective compound.

M.p.: 278.0 ~ 282.0C.
H-NMR (CDCl3 + DMSO d-6, TMS, ~ ppm): 7.29 (5H,s), 7.40 ~ 7.70 (9H,m) Synthesi~s Exa~ple 12 3-(4-tri;,~luoromethoxyph~yl)-5-iodo-6-(2-pyridyl)-~

2,4(1H,~)-pyrimidi~edione (co~eQ~d No. 3.4 of the presen~ inventlon) _ , ~ , ,, ~ , ':

- 65 - 203~404 1.0 g of ethyl 3-amino-3-(2-pyridyl)-2-propenoate was added dropwise to a 20 ml dimethylformamide solution of 0.26 g of sodium hydride (purity: 55%) under stirring at 0C. This solution was stirred at room temperature for 15 minutes and then added with 1.3 g of ethyl 4-trifluoromethoxyphenylcarbamate. The mixed solution was stirred at 100C for 3 hours and then the solvent was distilled away under reduced pressure. The residue was dissolved by adding 100 ml of water and washed with diethyl ether. The obtained aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice. Then precipitated crystals were filtered out and dried under reduced pressure to obtain 1.0 g of 3-(9-trifluoromethoxyphenyl)-6-(2-pyridyl)-2,4(lH,3H)-pyrimidinedione.
1.0 g of the obtained 3-(4-trifluoromethoxyphenyl)-6-(2-pyridyl)-2,4(lH,3H)-pyrimidinedione was added to 20 ml of dichloromethane, and 0.7 g of iodine monochloride was added thereto with stirring at room temperature. The resulting solution was further stirred at room temperature for 3 hours, then poured into 100 ml of water and extracted with 100 ml o~ ethyl acetate. The obtained organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 0.60 g of the objective compound.

.

M.p.: 215.0 ~ 217.0C.
H-NMR (DMSO d-6, TMS, ~ ppm): 7.20 ~ 7.95 (7H,s), 8.55 ~
8.75 (lH,m) Synthesis Example 13 3-(5-trifluoromethyl-2-pyridyl)-6-(2-chlorophenyl)-2~4(lH,3H)-pyrimidinedione (compound No. 4.4 of the present invention) ) 1.27 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate was added dropwise to a 20 ml of dimethylformamide solution of 0.26 g of sodium hydride (purity: 55%). The solution was stirred t room temperature for 15 minutes, then cooled to 0C and added with 1.24 g of methyl (5-trifluoromethyl-2-pyridyl)carbamate. The resulting solution was further stirred at 120C for 5 hours and then the solvent was distilled away under reduced pressure. The residue was dissolved with 100 ml of water and washed with diethyl ether. The obtained aqueous layer was added into a mixed solutlon of 20 ml of concentrated hydrochloric acid and 50 g of ice, and the precipitated crystals were filtered out and dried to obtain 0.21 g of the objective compound.

M.p.: 281.0 ~ 283.0C.
H-NMR ~CDCl3 + DMSO d-6, TMS, ~ ppm): 5.81 (lH,s), 7.40 ~ 7.60 (5H,m), 8.00 ~ 8.25 (lH,m), 8.75 ~ 8.90 (lH,m) "

- 67 - 2034~04 Synthesis Example 14 3-(2.6-dichloro-4-trifluoromethylphenyl~-6-trifluoromethyl-2.4(lH.3H)-pyrimidinedione (compound No.
5.8 of the present invention) A 20 ml dimethylformamide solution of 2.7 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added dropwise to a 20 ml dimethylformamide solution of 0.78 g of sodium hydride (purity: 55%) with stirring at 0C. After heated to room temperature under stirring for 15 minutes, the mixed solution was cooled to -30C and then added dropwise with 20 ml of a dimethylformamide solution of 3.8 g of 2,6-dichloro-4-trifluoromethylphenyl isocyanate.
The resulting solution was again heated to room temperature and stirred at 80C for 30 minutes. Then the solvent was distilled away under reduced pressure and the residue was dissolved by adding lO0 ml of water. This aqueous solution was washed twice with diethyl ether, then added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid, and extracted with ethyl acetate. The obtained organic layer was washed with water and dried, and the solvent was distilled away under reduced pressure to obtain 3.75 g of a crude product. This crude product was recrystallized from a mixed solvent of diisopropyl ether and isopropyl alcohol to obtain 1.65 g of the objective compound.

~ ' . -;~034~10~

M.p.: 248.0 ~ 250.0C.
H-NMR (CDC13 + CD30D, TMS, ~ ppm): 6.19 (lH,s), 7.71 (2H,s) Synthesis Example 15 3-(2~3~4-trifluorophenyl)-6-trifluoromethyl-2 4(lH 3H)-pyrimidinedione (compound No. 5.1 of the present invention) 1.28 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added to a 10 ml dimethylformamide solution of 0.33 g of sodium hydride (purity: 55~) under ice cooling and stirred at room temperature for 15 minutes, followed by addition of 1.31 g of ethyl 2,3,4-trifluorophenylcarbamate and was stirred at 90C for 4 hours. Then dimethylformamide was distilled away under reduced pressure and the residue was dissolved in 100 ml of water. This aqueous solution was washed with diethyl ether, then added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed with water and dried, and then the solvent was distilled away under reduced pressure to obtain 0.3 g of the objective compound~
M p.: 137.0 ~ 138.5C.
H-NMR (CDC13 + DMSO d-6, TMS, ~ ppm): 6.10 (lH,s), 6.80 ~ 7.20 (2H,m) ' ' - 69 - X034~04 Synthesis Example 16 3-(2 4.6-trichlorophenyl)-5-bromo-6-trifluoromethyl-2.4(lH.3H)-pyrimidinedione (compound No. 5.15 of the present invention) 3.6 g of 3-(2,4,6-trichlorophenyl)-6-trifluoromethyl-2,4(lH,3H)-pyrimidinedione and 4.1 g of sodium acetate were added to 30 ml of acetic acid, followed by dropwise addition of 6.4 g of bromine with stirring at room temperature. The resulting solution was stirred at 110C for 5 hours and then the solvent was distilled away under reduced pressure. The residue was extracted with 100 ml of ethyl acetate, and the obtained organic layer was washed with water and dried. Then the solvent was distilled away to obtain a crude product.
This crude product was washed with isopropyl ether and dried to obtain 1.8 g of the objective compound.
M.p.: 219.0 ~ 222.0C.
H-NMR (CDCl3 + CD30D, TMS, ~ ppm): 7.38 (2H,s~

Synthesis ~xample 17 1-ethoxymethyl-3-(2,9,6-trichlorophenyl)-6-trifluor~methyl-2 4l1H,3H)-pyrimidinedione (compound No.
5.20 of the pre~e~t invention) 1.50 g of 3-~2,4,6-trichlorophenyl)-6-trifluoromethyl-2,9(lH,3H)-pyrimidinedione was added to a 10 ml tetrahydrofuran solution of 0.30 g of sodium .
'' :

hydride (purity: 55%) with stirring under ice cooling, and the mixed solution was stirred at room temperature for 15 minutes. Then, after adding 0.70 g of chloromethylethyl ether, the solution was further stirred at room temperature for 3 hours. Then ice was added to the solution to decompose excess sodium hydride. The resulting mixture was extracted with 100 ml of ethyl acetate, and the obtained organic layer was washed thrice with water and dried over magnesium sulfate. Then the solvent was distilled away under reduced pressure to obtain 1.2 g of the objective compound as a viscous oily substance.
H-NMR (CDC13, TMS, ~ ppm): 1.18 (3H,t,J=6.0 Hz), 3.64 (2H,q,J=60 Hz), 5.38 (2H,s), 6.30 (lH,s), 7.37 (2H,s) Synthesis Example 18 3-(2~4,6-trichlorophenyl~-6-chlorodifluoromethyl-2,4~lH~3H)-~yrimidinedione (compound No. 5.56 of the present invention) 1.0 g of ethyl 3-amino-4-chloro-4,4-difluorocrotonate was added dropwise to a 10 ml dimethylformamide solution oP 0.24 g of sodium hydride (purity: 55~) with stirring at 0C. The solution was stirred at room temperature for 15 minutes, then cooled to 0C and added with 0.8 g of 2,4,6-trichlorophenyl isocyanate. The resulting solution was heated to room - ~ .

- 71 - 203~404 temperature and further stirred at 100C for 2 hours.
Then the solvent was distilled away under reduced pressure and the residue was d.issolved in 100 ml of water and washed with diethyl ether. The aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice, and the precipitated crystals were filtered out and dried under reduced pressure to obtain a crude product. This crude product was washed with a heated and mixed solvent of diisopropyl ether and isopropyl alcohol, and dried to obtain 0.65 g of the objective compound.
M.p.: 268.0 ~ 270.0C.
1H-NMR (CDCl3 + CD30D, ~ ppm): 6.14 (lH,s), 7.48 (lH,s) Synthesis E~ample 19 3~(2,4.6-trichlorophe~yl)-6-trifluoromethyl-(lH/3H)-pyr~mi~ne-2-~hiQn-4-one (compound No~ 5.75 of the present invention) A 5 ml dimethylformamide solution of 3.7 g ethyl 3-amino-4,4,9-trifluorocrotonate was added dropwise to a 30 ml dimethylformamide solution of 1.0 g of sodium hydride (purity: 55%) with stirring at 5C. The mixed solution was stirred at room temperature for 15 minutes, then cooled to 5C and added dropwise with a 10 ml dimethylformamlde solution of 5.0 g of 2,4,6-trichlorophenyl isothiocyanate. The resulting solution was heated to room temperature and further stirred at .- , , ~ .
"~ , :'.:

- 72 - 203440't 130C for 2 hours. Then the solvent was distilled away under reduced pressure and the residue was dissolved by adding 200 ml of water and washed with diethyl ether.
The obtained aqueous layer was added into a mixed solution of 30 ml of concentrated hydrochloric acid and 100 g of ice and extracted with 200 ml of ethyl acetate.
The obtained organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 2.8 g of a crude product.
This product was purified by preparative thin-layer chromatography ~developing solvent: a mixed solvent of chloroform and ethyl acetate) to obtain 0.43 g of the objective compound.

M.p.: 208.0 ~ 214.0C.
H-NMR (CDCl3 + DMSO d-6, TMS, ~ ppm): 6.39 (lH,s), 7.40 (2H,s), 9.60 (lH,bs) Synthesis Example 20 3-(~,4-diai~o-6-t~if~uoromethylphenyl)-6-trif~uoxomethyl-2,4(1H,3H)-pyrimidi~ed~o~e (compound No.
5.65 of this inYention) 1.0 g of 6-trifluoromethyl-2,4(lH,3H)-pyrimidinedione was added to 10 ml of dimethylformamide, followed by addition of 0.65 g of sodium hydride (purity:
55%) with stirring at 0C. The mixed solution was stirred at room temperature for 30 minutes, then cooled ~ 73 ~ 203440~

to 0C and added dropwise with a 5 ml dimethylformamide solution of 1.89 g of 2-chloro-3,5-dinitrobenzotrifluoride. After the solution was further stirred at room temperature for 3 hours, the solvent was distilled away under reduced pressure. After addition of cooled dilute hydrochloric acid thereto, the residue was extracted with 100 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and then the solvent was distilled away under reduced pressure to form a crude product. This crude product was recrystallized from a mixed solvent of chloroform and petroleum ether to obtain 0.77 g of the objective compound.
M.p.: 219.0 ~ 220.5C.
H-NMR (CDC13 ~ CD30D, TMS, ~ ppm): 6.10 (lH,s), 8.78 (lH,d,J=3.0 ~z), 9.08 ~lH,d,J=3.0 Hz) Synthç~l~ E~ample 21 3-(~ 4 6-trichlorophenyl)-6-bromo-2 4~1H 3H)-pyrimidinedione (compound~o. 5.81 Q~ _~h~_E~esent inventio~L
1.7 g of malonic acid dichloride was added dropwise to a 50 ml 1,4-dioxane solution of 2.4 g of 2,4,6-trichlorophenylurea with stirring at 0C. The solution was stirred at room temperature for 3 hours and then the solvent was distilled away under reduced pressure to obtain a crude product. This crude product was purified :' , ':

_ 74 _ 203~404 by silica gel column chromatography (developing solvent:
chloroform) to obtain 2.35 g of 3-(2,4,6-trichlorophenyl)-6-hydroxy-2,4(lH,3H)-pyrimidinedione.
10 ml of phosphorus tribromide was added dropwise to 0.60 g of pyridine with stirring at 0C and, after stirring this solution at 0C for 15 minutes, 1.6 g of the obtained 3-(2,4,6-trichlorophenyl)-6-hydroxy-2,4(lH,3H)-pyrimidinedione was added thereto. The mixed solution was stirred at 80C for 3 hours, then added into ice water and extracted with 100 ml of ethyl acetate.
The obtained organic layer was dried over anhydrous sodium sulfate and then the solvent was distilled away under reduced pressure to form a crude product. This crude product was recrystallized from a mixed solvent of hexane and isopropyl ether to obtain 0.62 g of the ob~ective compound.

M.p.: 187.0 ~ 190.0C.
H-NMR (CDC13 + CD30D, TMS, ~ ppm): 6.10 (lH,s), 7.45 (2H,s) Sy~ s Example 22 3-~2 6-dic~lD~o-4-triluoromethylphenyl)-6-methylthio-2,4(lH,3H~-pyrimidinedione ~compound No. 5.87 of the prese~ invention) 0.81 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-6-bromo-2,4(lH,3H)-pyrimidinedione was added to 5 ml of dimethylformamide, followed by addition of 0.35 g of ~ 75 ~ X 0 3 ~ ~ 0 4 sodium methyl mercaptide with stirring at room temperature. The solution was stirred at 80C for 2 hours, then cooled to room temperature, added to cooled dilute hydrochloric acid and extracted with 100 ml of ethyl acetate. The obtained organic layer was washed with dilute hydrochloric acid and water and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure to form a crude product. This crude product was recrystallized from a mixed solvent of hexane and isopropyl ether to obtain 0.33 g of the objective compound.

M.p.: 219.0 - 222.0C.
H-NMR (CDC13, TMS, ~ ppm): 2.48 (3H,s), 5.68 (lH,s), 7.76 (2H,s), 9.70 (lH,bs) The properties of the compounds produced according to the above Synthesis Examples are shown in Table 6 ~
10. (The representations given in these tables correspond to those in Tables 1 ~ 5).
The compound Nos. in Tables 6 ~ 10 will be referred to in the descriptions of Formulation Examples and Test Examples set forth below.

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Claims (14)

1. Uracil derivatives represented by the general formula (I):

(I) wherein R1 represents hydrogen atom, C1-4 alkyl group, C2-4 alkenyl group, C2-4 alkynyl group, C1-4 haloalkyl group, C2-4 alkoxyalkyl group, formyl group, C2-6 alkylcarbonyl group, C2-6 alkoxycarbonyl group, C3-6 alkoxycarbonylalkyl group, C2-6 cyanoalkyl group, benzyl group, phenyl group, -SR12 group [wherein R12 is C2-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, -NR13R14 group (wherein R13 is C1-6 alkyl group and R14 is C1-6 alkyl group, C2-6 alkoxycarbonyl group, C3-6 alkoxycarbonylalkyl group, C1-6 alkylsulfonyl group, C2-6 alkylcarbonyl group, C3-9 dialkylaminocarbonyl group, C2-6 dialkylaminosulfonyl group and phenyl group which may be substituted or non-substituted) and phenyl group which may be substituted or non-substituted (the substituent is selected from halogen atom, cyano group, nitro group, C1-4 alkyl group, C1-4 haloalkyl group, C1-4 alkoxy group, C2-6 alkoxycarbonyl group, C1-4 haloalkoxy group, C2-6 haloalkoxycarbonyl group, C2-6 alkylcarbonyl group, C2-6 haloalkylcarbonyl group, C1-4 alkylsulfonyl group or C1-4 haloalkyl sulfonyl group, and when the number of the substituents is not less than 2, the substituents may be same or different)], alkali metal or alkaline earth metal;
R2 represents hydrogen atom, halogen atom, C1-4 alkyl group, C1-4 haloalkyl group, C1-4 hydroxyalkyl group, C2-4 alkoxyalkyl group, C2-4 altylthioalkyl group, thiol group, C1-4 alkylthio group, C1-4 alkylsulfinyl group, C1-4 alkylsulfonyl group, C1-4 haloalkylthio group, C1-4 haloalkylsulfinyl group, C1-4 haloalkylsulfonyl group, hydroxyl group, C1-4 alkoxy group, C1-4 haloalkoxy group, formyl group, cyano group, nitro group or thiocyanate group;
Z1 and Z2 represent independently oxygen atom, sulfur atom or imino group;

A represents [wherein X is halogen atom, C1-4 alkyl group, C1-4 alkoxy group, C1-4 alkylthio group, C1-4 haloalkyl group, C1-4 haloalkoxy group, C1-4 haloalkylthio group, amino group, cyano group or nitro group, and I is an integer of 0 to 5 (when I is an integer of 2 to 5, the substituents X may be same or different)], ox naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituent of the above aromatic groups is selected from halogen atom, C1-4 alkyl group, C1-4 alkoxy group, C1-4 alkylthio group, C1-4 haloalkyl group, C1-4 haloalkoxy group, C1-4 haloalkylthio group, amino group, cyano group and nitro group, and when the number of the substituents is not less than 2, these substituents may be same or different), C1-6 haloalkyl group containing one or more fluorine atoms, halogen atom, cyano group, nitro group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, or C2-6 alkoxycarbonyl group; and when A is (where X and I are as defined above), or naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituents of the above aromatic groups are the same as defined above), B is [wherein Y1 is halogen atom, C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-6 cycloalkyl group, C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, C3-6 halocycloalkyl group, C2-6 cyanoalkyl group, C1-6 hydroxyalkyl group, C2-6 carboxyalkyl group, C1-6 alkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, C3-6 cycloalkyloxy group, C1-6 haloalkoxy group, C2-6 haloalkenyloxy group, C2-6 haloalkynyloxy group, C3-6 halocycloalkoxy group, C4-7 halocycloalkylalkoxy group, C1-6 alkylthio group, C2-6 alkenylthio group, C2-6 alkynylthio group, C3-6 cycloalkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C2-6 alkenylsulfinyl group, C2-6 alkynylsulfinyl group, C3-6 cycloalkylsulfinyl group, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl group, C2-6 alkenylsulfonyl group, C2-6 alkynylsulfonyl group, C3-6 cycloalkylsulfonyl group, C1-6 haloalkylsulfonyl group, C2-6 alkoxyalkyl group, C2-6 alkoxyalkoxy group, C2-6 haloalkoxyalkyl group, C2-6 haloalkoxyalkoxy group, C2-6 alkylthioalkyl group, C2-6 alkylthioalkoxy group, C3-6 alkoxycarbonylalkyl group, C3-6 alkylcarbonylalkyl group, C2-6 alkoxycarbonyloxy group, C2-6 alkylcarbonyl group, C3-6 alkenylcarbonyl group, C3-6 alkynylcarbonyl group, C4-7 cycloalkylcarbonyl group, C2-6 haloalkylcarbonyl group, C2-6 alkoxycarbonyl group, C2-6 haloalkoxycarbonyl group, C3-6 alkoxycarbonylalkoxy group, nitro group, cyano group, hydroxyl group, carboxyl group, thiocyanate group, isothiocyanate group, C2-6 thiocyanatealkyl group, C1-6 alkylsulfonyloxy group, C2-6 alkylthiocarbonyl group, amino group (-NR3R4), aminocarbonyl group (-CONR3R4), aminocarbonyloxy group (-OCONR3R4), amide group (-NR3COR4), alkoxycarbonylamino group (-NR3CO2R4), aminosulfonyl group (-SO2NR3R4), thioamide group (-NR3CSR4), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group, trimethylsilyl group or Ar group (wherein W is , , , , , -C?C-, -N?N-, , , , , or (in which R3 and R4 represent independently hydrogen atom, C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, C2-6 alkylcarbonyl group, C2-6 alkoxycarbonyl group, phenyl group or benzyl group; R5 and R6 represent independently hydrogen atom, halogen atom, C1-6 alkyl group, C3-6 cycloalkyl group, cyano group or phenyl group; and q is an integer of 0 to 2); is an integer of 0 or 1; and Ar is phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group which may be substituted or non-substituted (the substituent of the above aromatic groups is selected from halogen atom, cyano group, nitro group, C1-4 alkyl group, C1-4 haloalkyl group, C1-4 alkoxy group, C1-4 haloalkoxy group, C1-4 alkylthio group, C1-4 haloalkylthio group, C1-4 alkylsulfonyl group, C1-4 haloalkylsulfonyl group, C2-4 alkoxycarbonyl group, carboxyl group, amino group, C1-4 monoalkylamino group, C2-8 dialkylamino group, phenyl group, benzyl group, methylenedioxy group or halomethylenedioxy group, and when the number of the substituents is not less than 2, the substituents may be same or different)); and m is an integer of 0 to 5 (when it is 2 to 5, the substituents Y1 may be same or different)], or naphtyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimizyl group, pyrazyl group, quinolyl group, quinoxalyl group, benzofuryl group, benzothienyl group, indolyl group, benzoxazolyl group or benzothiazolyl group which may be substituted or non-substituted (the substituent of the above aromatic groups is selected from halogen atom, cyano group, nitro group, C1-4 alkyl group, C1-4 haloalkyl group, C1-4 alkoxy group, C1-4 haloalkoxy group, C1-4 alkylthio group, C1-4 haloalkylthio group, C1-4 alkylsulfonyl group, C1-4 haloalkylsulfonyl group, C2-4 alkoxycarbonyl group, carboxyl group, amino group, C1-4 monoalkylamino group, C2-8 dialkylamino group, phenyl group, phenoxy group or benzyl group, and when the number of the substituents is
2 or more, the substituents may be same or different), and when A is C1-6 haloalkyl group containing one or more fluorine atoms, halogen atom, cyano group, nitro group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, C1-6 alkoxy group, C1-6 haloalkoxy group or C2-6 alkoxycarbonyl group, B is [wherein Y2 is halogen atom, C1-4 alkyl group, C1-4 alkoxy group, C1-4 haloalkyl group, C1-4 haloalkoxy group, C1-4 alkylthio group, C1-4 haloalkylthio group, C1-4 alkylsulfinyl group, C1-4 haloalkylsufinyl group, C1-4 alkylsulfonyl group, C1-4 haloalkylsulfonyl group, sulfonamide group, C2-4 alkenyl group, C2-4 haloalkenyl group, amino group, C1-4 monoalkylamino group, C2-8 dialkylamino group, C2-6 alkoxyalkoxy group, C2-6 alkoxycarbonyl group, cyano group or nitro group, and r is an integer of 3 to 5 (the substituents Y2 may be same or different, and when r = 3 with the substituents at the 2-, 4- and 5-positions, the substituent Y2 at the 5-position is not C1-4 alkoxy group, C1-4 haloalkoxy group, C2-6 alkoxyalkoxy group or C2-6 alkoxycarbonyl group)], provided that A is not phenyl group and 3-bromo-4-methoxyphenyl group, when B is phenyl group.

2. Uracil derivatives according to Claim 1, wherein in the general formula (I), A is (where X and ?

are as defined above), or naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituents are the same as defined above), and B is (wherein Y1 and m are as defined above), or naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group, quinoxalyl group, benzofuryl group, benzothienyl group, indolyl group, benzoxazolyl group or benzothiazolyl group which may be substituted or non-substituted (the substituent are the same as defined above), provided that A is not phenyl group and 3-bromo-4-methoxyphenyl group, when B is phenyl group.
3. Uracil derivatives according to Claim 2, wherein in the general formula (I), A is (wherein X and ?

as defined above), and B is (wherein Y1 and m are as defined above), provided that A is not phenyl group and 3-bromo-4-methoxyphenyl group, when B is phenyl group.
4. Uracil derivatives according to Claim 2, wherein in the general formula (I), A is naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group or pyrazyl group which may be substituted or non-substituted (the substituent are as defined above), and B is (where Y1 and m are as defined above).
5. Uracil derivatives according to Claim 1, wherein the general formula (I), A is C1-6 haloalkyl group containing one or more fluorine atom, halogen atoms, cyano group, nitro group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, or C2-6 alkoxycarbonyl group, and B is (wherein Y2 and r are as defined above).
6. Uracil derivatives according to Claim 3, wherein the general formula (I), R1 and R2 represent hydrogen atom, Z1 and Z2 represent oxygen atom, A represents 2-fluorophenyl group, 2-chlorophenyl group, 2-chloro-6-fluorophenyl group or 2,6-difluorophenyl group, and B represents (where Y1 and m are as defined above).
7. Uracil derivatives according to Claim 5, wherein in the general formula (I), R1 and R2 represent hydrogen atom, Z1 and Z2 represent oxygen atom, A represents trifluoromethyl group, pentafluoroethyl group or chlorodifluoromethyl group, and B represents (wherein Y2 and r are as defined above).
8. Pesticides comprising as an active ingredient a pesticidally effective amount of at least one of the uracil derivatives set forth in Claim 1, and a pesticidally acceptable carrier or diluent therefor.
9. Insecticides and acaricides comprising as an active ingredient an insecticidally and acaricidally effective amount of at least one of the uracil derivatives set forth in Claim 2, and an insecticidally and acaricidally acceptable carrier or diluent therefor.
10. Insecticides and acaricides according to Claim 8, wherein said active ingredient is at least one of the uracil derivatives set forth in Claim 3.
11. Insecticides and acaricides according to Claim 8, wherein said active ingredient is at least one of the uracil derivatives set forth in Claim 4.
12. Insecticides and acaricides according to Claim 8, wherein said active ingredient is at least one of the uracil derivatives set forth in Claim 5.
13. Herbicides comprising as an active ingredient a herbicidally effective amount of at least one of the uracil derivatives set forth in Claim 5, and a herbicidally acceptable carrier on diluent therefor.
14. A process for producing the uracil derivatives set forth in Claim 1, which comprises reacting the compounds represented by the general formula (XXXVI):

(XXXVI) (wherein R1, R2, Z2 and A are as defined above, and R7 represents C1-6 alkyl group, benzyl group or phenyl group) with the compounds represented by the general formula (IV) or (V):

(IV) (V) (wherein B and Z1 are as defined above, and R8 represents C1-6 alkyl group, benzyl group or phenyl group).
CA002034404A 1990-01-18 1991-01-17 Uracil derivatives and pesticides containing the same as active ingredient Abandoned CA2034404A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP8826/90 1990-01-18
JP882690 1990-01-18
JP5345090 1990-03-05
JP53450/90 1990-03-05

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CA2034404A1 true CA2034404A1 (en) 1991-07-19

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KR (1) KR0149513B1 (en)
CA (1) CA2034404A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12022833B2 (en) 2018-07-05 2024-07-02 Sumitomo Chemical Company, Limited Uracil compound and composition for controlling harmful arthropods comprising the same

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JP4528196B2 (en) * 2004-04-30 2010-08-18 独立行政法人科学技術振興機構 Method for producing pyrimidine derivatives

Family Cites Families (2)

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Publication number Priority date Publication date Assignee Title
US3497515A (en) 1966-02-04 1970-02-24 Du Pont 3,5,6-substituted uracils
US3981715A (en) 1972-03-24 1976-09-21 American Cyanamid Company 2,3,5-Substituted-6-trifluoromethyl-1,3-diazin-4-ones herbicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12022833B2 (en) 2018-07-05 2024-07-02 Sumitomo Chemical Company, Limited Uracil compound and composition for controlling harmful arthropods comprising the same

Also Published As

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KR910014359A (en) 1991-08-31
JPH03287578A (en) 1991-12-18
KR0149513B1 (en) 1998-10-15
JP3038903B2 (en) 2000-05-08

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