JPS62111961A - Insecticidal 1-(4-aryloxyphenyl)-3-benzoyl urea compound andits production - Google Patents

Abstract

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

Description

DETAILED DESCRIPTION OF THE INVENTION Summary of the Invention Field of the Invention The present invention is directed to novel 1-(4-aryloxyphenyl)-6-benzoyl urea compounds useful as active poisons in insecticidal compositions. The present invention also provides the following features:
(I was inspired by the method for producing a 4-aryloxyphenyl-6-benzoyl urea compound.

The invention further relates to insecticidal compositions and methods of using them.

BACKGROUND OF THE INVENTION PRIOR ART AND PROBLEMS In recent years, various benzoyl urea compounds have been reported in the literature to have insecticidal activity. For example, pyridyloxyphenylbenzoyl ureas and their use as insecticides are described in US Pat. No. 4,3 issued January 12, 1982.
No. 10,530 and US Pat. No. 4,344,951, issued Aug. 17, 1982. In addition, Japanese patent application No. 5 Otsu 099, 56 published on June 21, 1982, describes biridyloxin phenylbenzoyl urea compounds and their use as insecticides.
No. 9, published on July 8, 1982, Japan l,! ill'
P! j Hide Ken 5 Otsu 1 0 9, 7 6 8, 198
Japanese patent application published on September 6, 2015 5 7, 1 4
4, 2 5 No. 8, Japanese patent application No. 5 Otsu 114,259- published on September 6, 1982, Japanese nationality Kyoda M 5 7, 1 4 5, 8 published on September 9, 1982
6 Disclosed in No. 1.

Japanese patent application for phenoxybenzoyl urea compound published on March 1, 1983 5 8, 0 5 5, 1 6
No. 5 and Japanese Patent Application No. 5 published on March 3, 1986
8, 039, 657.

Accordingly, one or more of the objects set forth in item F are achieved by practice of the present invention. The purpose of the present invention is to obtain fi-regular 1-(
An object of the present invention is to provide a 4-aryloxyphenyl)-6-benzoyl urea compound.

Another object of the present invention ii. Predetermined 1-
An object of the present invention is to provide a (4-aryloxyphenyl)-6-benzoyl urea compound. A still further object of the invention is to prepare novel benzoylurea compounds, such as 1-[3-
Chloro-4-(2,4-dichlorophenoxy)-5-dimethoxymecal-2-methylphenyl) - s -
(2.6-difluorobenzoyl)urea, 1-[3
-Chloro-4-(2.4-dichlorophenoxy)-5-formiIL/-2-)terphenyl:)-1-
(2,6-difluorobenzoyl)urea, 1-[6-chloro-4-(2,4-dichlorophenoxy)-5-hydroxymethyl-2-methylphenyl) - 5 - (
2. 6-difluorobenzoyl)urea, 1-[5-
Calhoki2-6-chloro-4-(2.4-dimethylphenoxy)-2=mecarphenyl: ]-3-
(2. 6-difluorobenzoyl)urea, 1-[
3-Chloro-4-(2,4-dimethylphenoxy)-
5-(2-methoxycarbonyl-1-ethynyl)-2-
methylphenyl]-s-(2, (S-difluorobenzoyl)urea, etc.).Another object is to provide a method for producing novel benzoyl urea compounds.A further object is to provide a novel method for producing benzoyl urea compounds. It is an object of the present invention to provide novel insecticidal compositions containing benzoyl urea compounds as active poisons.Another object of the invention is to provide a method of controlling pests by applying the novel insecticidal compositions. These and other objects will be readily apparent to those skilled in the art in light of the teachings contained herein.

DISCLOSURE OF THE INVENTION Means for Solving the Problems In a broad aspect, the invention provides novel 1-(4-79-ruoxypheny/l/)-3-benzoyl group X compounds, insecticidal compositions containing the compounds, and Concerning the manufacturing and usage method. The benzoyl urea compounds of the present invention can be represented by the formula: independently represents herogen, alkyl, alkoxy, nitro or cyan; m has a value of 0 to 2; R1 is an acyclic or cyclic acetal group, an acyclic or cyclic ditheoacetal group, Represents an acyclic or cyclic hemicaoacetal group, aldehyde group, carboxylic acid group or its ester derivative, hydroxyalkyl group, alkoxyalkyl group, acyloxyalkyl group, alkenyl group or alkylcarbonyl group, provided that R1 is carbonyl In the case of an acid group or its ester derivative, m must have a value of 2, and fLl must be located at the 2-position or the 6-position; 2 is (1 ) a substituted or unsubstituted saturated or unsaturated monocyclic ring system or a substituted or unsubstituted saturated or unsaturated bicyclic fused ring with (II), wherein at least one JJi#' i is a 6-membered unsaturated carbocyclic ring and the second ring may contain 5- or 6-negative carbocyclic or carbonyl groups or 1 or 2 oxygen or ionic atoms in any combination; a 5- or 6-membered heterocyclic ring).

DETAILED DESCRIPTION In light of the foregoing, the invention is directed to novel 1-(4-aryloxyphenyl)-6-benzylurea compounds, insecticidal compositions containing the compounds, and methods of making and using them.

Preferred benzoylurea compounds within the broad general formula (1) are those having the formula F: (wherein X□,
l, X8, itl and Yl are the above-mentioned power, Y has the meaning independently described for Yl, R1 and
are independently hydrogen, halogen, alkyl, polyheroalkyl, nitro or cyano, 几 is hydrogen, halogen, alkyl or polyheroalkyl).

Particularly preferred benzoylurea compounds are those described in F: where Xl, x, R1, R1, R1, Y, and Y.

is the above-mentioned power); (wherein, X□, X8, L and R8 are the above-mentioned power)
.

The benzoyl urea compounds listed in Tables A-H of Section F are the above (
I) Illustrate what is included in the formula and can be made by practicing the invention: Table - Person F F HOH,010101Hol f(
HO bird 01 01 01 HF HHOH,0
10101H Table A (continued) liI F FOR,010101H'I?
01 HOH, 010101HF
F HOH,01Er 01 Hol
HHOH,01Br 01HF
HHOH,01Br 01 HF F
F OH, Pull Br 01 HF HF OH
,0IBr 01 HF 01
HOH,01Br 01 HF F
HOH,010H,OH,Hol HHOH
,01CH,OH,HF HHOH,010H,
OH,HFFF σH,010H,OH,HF
01 HOH, 010H, OH, HF
F HOH, Of Br Br H
ol HHOH,0IBr Br HF
HHOH, Of Br Er HF
F F OH,0IBr Br
HF 01 HOH, 01Br
Er HF F HOH, OIH01
Hol HHOH, OIH01H FHHO Melon 01 f (01H People (continued) F F FO bird 01 H01HF
01 HOH, OIHCI HF
F HOH,01H013-0101HHOH,0
1H015-01 F HHOH, 01H01! l-01F F
F OH, 01H013-01F 01
HOH, 01H013-01F F H
OI(, 010H, 015-OH.

01 HHOH, 010H, 015-OH.

F HHOH, 010H, 015-OH.

F F F OH, 010, 01
5-OI(.

F 01 HOH, 010H, 015-01 (
.

F F HOH, 010H, Er 5-O
H.

01 HHOH, 010H, Br 5-OH.

F HHOH, 010H, Br 5-OH.

F F F OH,010H,Br
5-OH.

F 01 HOH, 010H, Er 5
-OH.

F F HOH, CII Hlit
HF F HOH, 01 (7F, CI
HF HHOH, OIH011',
HF F FO also 01HOF, H table A
(continued) F 01 HOH, OIHOF, HF
F HO, H, 01HH3-OF.

F OH, 01J (H3-OF.

F F HOH, 010H, Br Hol
HHOH,010H,Br HF HH
OH,010H,Br HF F F
OH, 010H, Br HF 01H
OH,010H,Br HF F l
fH010101HolHHH010101H F F FH010101HF F
HH01Br 01 Hol H
11H01Br 01 HF HHH0
1Br Of HF FF
H0111r 01 HF 01
HH01Hr 01 HF F
HH011101HolHHH0III 01
HF F FH011101HF
F HOH, Br 01 01
Hol HII OH,,Br 01 0
1 H clothes (continued) F M HOH, Br 01 01
HF FF OH,Br
01 01 HF 01 HOH,B
r Of 01 HF F
HOH, Br Br 01 Hol
HHOH, Br Br 01 HF
HHOH, Br Br 01 HF
F F OH, Br Br 01
HF HF OH, Br Br
Of HF 01 HOH, Er
Br 01 HPI/H: σH, Br
H01Hol kl J(OH,Er
H01HF FF OH,B
r H01HF 'If HOH,]
(0101Hol fl HOH,H0101
HF F IF OfI, H01
01HF 01 HOH, HOf 01
HF F HOH, HBr 0
1 Hol HHOH, HBr 01
HF HHOH, HBr 01 HF
F F OH, HBr 01
HF HF OH, fl Br
01 H table (continued) F 01 HOH, HBr 01
HF F I (010101011 (01
HH01010101H F li' F 01 01
01 01 HF F H010
1Br 01 Hol HII 01
0f Jar Of HF
HH0101Br Of HF 01
H010f Br 01 HF
F HOn 01 J (01Ho
l HJ(0101H01H F F HHOH,0101Hol
HHHOH,0101)I F P F f(oH,0101HF
F HH□H,Br 01 Hol
HHf[OHBr 01 HF HH
HOH, Br 01 HF P
F HOH, Br 01 HF F
HHOH, HCI Hol HHHO
H, M 01 HF F 1?
HOH, H01HF 01 HHOH
, J (01H Table A (continued) F B' H010 le 01 01 1 (01HH
010H,0101H F F F 01 0H,0101HF F
H01(IH, Br 01 Hol HH01
0H,Br 01HF HH010H,Br
Of HF]! ' F 01 0H, Er
01 HF HF 01 0H, Er 0
1 HF 01 H010H, Br 01
H table B F F HO) I, H0101H F F HOH, HOH, OH, H Next 13 (continued I\) F F l' (Jll, H01
1, Off, HF F HOIL,
ni■lJr 01 HF F
HHO,H,J3rOf l(F
F H010101,01HF F
1-I 01 01 J, (Ochi HF
F F 01 01 . 1. (
OF, HF F H0101Br
01 Hol HH0101Er
01 HF HH0101-Or 0
1 HF F H0101 (Monday
01 5-OH.

F F H0101, E' F
HF F H010101H5-0
1F F I (0101H) I 3
-OF.

Front C Cloth C (continued) F 1! ' ](01(C101
011(H'OH,0101 F F HOH,01HF
F F OH, 0101F
01 H0110101F
F HOH,01Br01H
HOH,01Br F F F OHCI
BrF 01 HOH80
1BrF F HOH010H.

F F F OH010
H.

F F li H010
101HHH0101 F F F H0101
F F HOHH0101f(H
OH, H01 F F F OH, H0
1F C1HOHH01 F F HOHBr 0
1CI HHOH, Br OfF
F F OH, Br
01 Table C (continued) F F H01010101
Hj (010101 7F F 01 0
1 017 F
H)l OH0101HI(fl
OH01 F F F f(OK
, 01Table D 2 2ra---in, -y±---Y, --also -F F )I Oll, 01 0101
HM Off 01 01F I' J! '
OH,01IIF F F OH,0101 F 01 H011,0101 Table D (continued) F F HOH,01Br01
HJ(OH,01Br F F F OH,01B
rF 01 HOH, 01BrF
F HOH, 010H.

F F FO horse 01 0H
.

F F HH010101HHH01
01 F F P H0101F
F HOH, H0101HHO horse
H01 F F F OH, H01F
01 H0HIIH01F
F H010H, 01 table E F F ■■Oft, 01
Br Br01 HH011
,01Br BrF F
F O,f(,01Br BrF
01 H01(, 01Br
BrF F HJ (01B r
13 ro 1 J(H)I
01 B r B rF
F k' H01Er
BrF F HOH, HB
r Br01 HHOH, HBr
BrF F F
011. HBrBrF
F HOH, Br Er
ErC1l(HO)■, Br Br
BrF F B'
OH, Br Br BrF
F HOl 01
, Br BrF F
l! ' 01 01 B
r ErrF (continued) F F HHOH, Br BrF F
HOH,01HH ol HHOH,01HH F F F OH,01HH table F F F HOH,0100,OH,010101HHO
H,C! l 00. OH,0101F F H010H
,00,OH,01HF F HOH,C100,OH
,Br 01F HHOH,0100,OH,Br 0
1F FF OH,0100,OkL,Br 01F
F HOH,0100,OH,OHOHHF (continued) 01 HHO)I, 01 00,0)I,
OH0)IF F F OH,01
00, OH, Oli, OH.

F F I(H0100,0,1(,0101F
F HH01000HH01F F HH
OH,00,On, H01F F
HOH,0100,OH,OF,01
0101 HHOH,0100,0)i,OF,
01 01F FF OH,010
0,0)1. OF, 01 01F F
HOH,0100,OH,OF,Br
OfF HHOH,0100,OH,OF,
Br 01F FF OH,0100,O
H,OF, Br 01FFHO horse 0
1 on(ooa,), 01 0101
HI(01(,010H(OOH-,0101F
01 HOH, 010H (OOH,), 01
01F F HOH,010H(OOH,),
Br 01F HHOH,010H(OO
H,), Br 01F 01 HOH,
010H(OOH,), Br OfF
F F OH,010H(OOH,),
Br 01F F HOH,010H(0(01
(,),0) 01 0101 HH0H301
0H(O(01(,),0) 01 01F F
F OR, 010H [0 (OH, 80)] 01
01 Table F (continued) F F HOH,010H(0(OH,),O:]
Br 0101 HHOH,010H(O(OH
,),O) Br 01F HHOH,Of 0
H(0(OH,),0]Br 01F F F
OH,010,H (0 (0 horse), o) Br 0
1F F HOH,010H(0(OH,),O)
OH, OH.

F F HOH,010H(O(OH,),0)
f(01F F HOH,0100,H0101
F F HOH, 0100, HBr 01F
F HOH, 0100, HOH, OH.

F F 11 0H,010H,OH01Of,F
F F OH, 010H, 0:EI
01 01F F HOH,010H,OHBr
011F HHOH, 010H, OHBr 01
F ki F OH,010H,OHEr 0
1F F F OH,010H,OHBr 0
1F F HOH, 010H, 0001-OF,
Er 0101 HHOH,010H,0001=
OF, Er 01F F HOH,010H
(OOH, OH,), Er 01F F F
OH,010H(OOR,OH,), Br
01F 01 HOH,010H,OOH,Br
01F F HOH,0101(,OOH,Br
01 Table F (continued) 01 HHOH, 01CIH, 0011, Br
01A HHOH,Of OH,OO■I,
Br 01F FF OH1010
H, OOH, Br 01F HF OH, Of
OH, OOH, Br 01F F HOH,
0101(,OOH,OR,OH.

F F' F OR, 010H, OOH, OH,
Oh.

F F HOH, 010H, OOH, H01F
F HOH, 010kl, OOH, F FF
F HH010H, OCR, Of 01F F
HK 01 0kifOOH, Br 01
F F HOH,010H*OOI(mOFm
01 0101 HHOH,010H,OO,l
I, OF, 01 01F P IF
OK, 01 0H100kl, OF, 01
01F F HOH,010H,00,li,
OF, Br 0f01 HHOH,01
0H,0(JH,OF, ,Br 01F
HHOH,Of O,LI,00)(,OF,
Br 01F FF OH,010H
,0(III,OF,Br 01F 01H
OH, 01CIH, 0OLI, OF, Br
01F F HOH,01011,0OOOH,0
101F F HOH, 010H, 0OOOH, B
r 01F F HOH,Er OHO01
01 Table F (continued) F F HOH,010HO0101F F
l(01(,010HOBr 01F F HO
H,010f(-OI(0000H,0101F l
' fl OH, 010H HOOOOOOH, OH
,OH.

F F F OH,010H=0. HOOOOOH
,OH,OR.

F F HOH,010H-QHOOOOH,Br
01F HHOH,Of 0H=OHOOOOOH
,Br 01F F F OH,010H-O
HOOOOH,Br 01F F HOH,01
0H-0(01), 01 0101 HHOH
,010H=O(01), 01 01F F
F OH, 010H 0 (01), 01
01F 01 HOH, 010H=O(01),
01 01F 11 HOn, 010H-
0(Br), 01 01F F HOH,
010H=O(Br), Br 0fFFHO
Bird 010H-OHN0. 01 017 F
HOH,010H-OHNO,Br 01FFHO Horse 010H=0)1ON 01 01F F
HOH,010H=OHON Br 01F
F Holilol 0H-0(OOOOOH,),
atolF F HOH,010H=0(
C100OH,), Br 01F F l(
OH, 00 bird 00H, HNO.

Table F (continued) F　F　HOH, HOH, OOH, 01NO.

F F HOH,,1(OH,OOH,HONF
F HOH, HOH, OOH, 010F.

01 H110H, J(0)f, OOH, Of OF
.

F F HOHH0HOOHOF, 01a F
F OH, HOH, OOH, 010F.

F 01 HOH, E OH, OOH, 010F.

01 HHOH, 010H (OOH,), Br
01F HHOH, 010H (OOH,),
01 01F F HOH,010H,OOH
,010101HHOH,0100,OH,Br 01
F F HOH, 0100, OH, OH, Br
01F HHOH, 0100, OH, OH, Br
01F F HOH,0100,OH,0H(OH
, ), Er 01F HHOH,0100,O
H, 0H (OR,), Er 01F F H
OH,0100,OH,0H=OH,Br 01F
F HOH,0100,OH,0wOHBr 0
1F F HOH,0100,OH,0H-001
,Br 01F F HOH,010H,OOH
,0=OHBr 01F F HOH,010H
,OOH,0H(OH,),Br 01F F
HOH, 010H, 00H, 0 horse 00. ) I, Br
01 Table F (continued) XIX, X, YIY, R11'L, R.

F F HOH,0101-1-, (0011,O
H, OH, OH,), Br 01F F ki
OH, 010H, OOH, OH, 01Br 01F
F HOH,010H,0(OH,)40n,
Er 01Cmai[o(JR F F HOH,01("LCHJOs"y:)s
Br 01F F HOH,010(0)0-
n-0,H,,Br 01F F HOH,010
H=OHOH,0101F F HO horse 01 oa
=o(on,), 0101F F HOH
,010H=OH(OH,),OH,0101F F
fl OH,010H(SOH,), 0
10101 HHOH,010H(Son,),
0101F F HOH,0101((80H
,OH,O) 010101 HHOH,010)
I(801(,OH,O) 0101F F
HOH,010l-1(SOH,), F
Fol 1(HOH,010H(SOH,),
F iFF F H[11(,010M(80
H,), 0101FFHO horse 010H (SO
] = I, Bird Br 01F F HOH, 010H (
80H,), J! FF F HOH
,010M(80H,), ,Br 01F
F T(OH,010J([5(OH,),8)
Br 01F F HOH,010H(SOH
,OH,0) Br 01 table G X, X, X, Y, Y, RI
R.

F F HOH, 010000H, 0101H
HOH,01000011,01,yoi H
OH, oi ooooll, o
iF 1? FOH,010000LI,
01F F HOH,01
0L(,001■, 0101HH
OH,010H,0(IHl 01F
F F OH,010H,0OJ(,01F
F HHOH, OH, OOH, 0101HHH
OH,OH,0OH101 F F HOH,H01(,001(,01F
P H01010HOOH0101HH01
010HOOH01 F F HOH,01011IO(JH,OH
.

F F HOH,010,H,OOH,HF
F HOJ(,010H(OOH,OH,),
01 Table G (continued) X X X Y Y RlR.

F F HOH,010H(OOH,),
01F F HOH,010H(0-(OH,)
, -0) 01F F HOH,0100tH0
1F F HOH,010H,OH01F F
HOH,010H,0OOOH,01F F H
OH,010HO01 F F HOH,010H,0OO1=0(F),
01F F HOH, 010H=0(01),
01F F HOH, 010H=OHN
0. 01F F HOH, 010H-OH
ON 01F F HOH,010H=O
HOOOOH,01F F HOH,010fI(
SOII,), 0101 HHoH,010
H(SOH,), 01F F HOH,
010H (80H, Oli, 0) 01F F
HOH,010H(SOII,), 01 table ■ F F HOf(,0100,On, 0101
HHOH,0100,OH,01F 01 HOH,0
100,01(,01F F F OH,0100,O
H,017F HOH,0101(,OOH,0f01
HHOH,01011,OOH,01F F
F OH,010,fI,001[,01F F H
HBr 01 (00H01 F F HOH, Br OH, 00kl, 01F
F F OH, Br Oli, OOH, 01F F
HOH, OH, Okl, 0011. OfFF
HOH,J(OH,OOH,0101HHOH,Ii
OH, OOH, 01F l' HOH, HOH, 0
OII, OH.

F F H010f 0HOOH01 Table H (continued) F F HOH,010J(, (00 bird), OIF
F HOf(,010L((80 birds)t
01F F HOH, 010H (80H,),
01F F M OH, 010l-I (
SOH, 0, H, O) 01F F HOH,
010l-I(OOH,OH,), 01F F
HOH,010)I(OOH,), 01
F F HOH,01oH(o-(a,a,)s-
0) 01F F HOH,0100,H01F
F HOH,010H,OJ(01F F
HOH,010H,0OOOH801F F)I
01(,010HO01F F HOH,01
0H,0001=0(F), OfF F H
OH, 010H=0(01), 01F F
HOH,010H-OHN0. 01F
,F HOH,010H=OHON 01
F F HOH, at OH 0HOO, OH,
01 Table Engineering F F HOH,0100,On, Br Br0
1 HHOH,0100,Ou, Br BrF
F HHOH,00,OH,Br ErF li' H
OH,01ONchi00]i, Br BrCl H
HOH,010H,OOH,Br BrF F F O
H,010H,OOH,Er ErF F HOH,B
r OH, OOH, Br Er01 HHOH, Br
OH, OOH, Br ErF F F OH, Br O
H, OOH, Br ErF F HOH, HOH, OO
H,Br BrF F HH010H,OOH,Br
BrF F H01010H, OOH, Br Er01
HH01010HOOHBr ErF F HOH,
010fl, OOH, HHF F HOH, Br OH
, OOH, HH table ■ (continued) F F HOH, 0101 (, 0001-0 (F)
, HHF F HOH,010H(OOH,O
ff, ), Br BrF F HOH, CI
0f((0(IH,), Er BrF
F HOH,010M(0(-OH,),-〇)
Br BrF F HOH,0100,HBr B
rF F HOH, 010H, OHBr BrF
F 11 0H, 010H, OOH, OF,
Br BrF F HOH,010H,0OOOO
H, Br BrF F HOf(,010HOBr
BrF F HOH,010H=O(01),
Br BrF F HOH,010H-OH
NO, Br BrF F HOH, 010H=OH
ON Br BrF F HOH,010
H=OHOOOOOH, Er BrF F Hom,
alon(son,), Br 13rF
F HOH, 010H (SCM, OH, O)
Er BrF F HOH,010H(SOH,)
The novel benzoyl urea compounds of the present invention included in the formula , Er and react according to the following general scheme - organic
- Scheme E, where Xl, Xl, bird, Y,, m5R1 and 2 are (1
) has the meaning stated in the formula.

Alternatively, the new compound combines aryloxyphenyl isocyanate 4 with benzamide 5 and the following general scheme ■
It can be made by reacting according to the following.

Scheme ■ Here, Xo, X2, Xl, Y, , m, R1 and 2 have the meanings described in Formula 9, except that R1 is not a hydroxyalkyl group or a carboxylic acid group.

The subject compounds also include benzoyl chloride 6 substituted urea 7
and can be made according to the following plethora of schemes ■.

: 2 deni 2\ben- Here, Xl, X2, X,,Y,, m1几□ and 2 are R
It has the meaning described in formula (1) except that 1 is not an acyclic or cyclic acetal group, aldehyde group, carboxylic acid group or hydroxyalkyl group.

The reactions shown in Scheme E, (1) and (2) can usually be carried out in an organic solvent such as an aromatic hydrocarbon, a helogenated hydrocarbon, or an ether.

Toluene, t2-dichloroethane, dichloromethane, p
- Solvents such as diochitin are preferred. These reactions proceed at temperatures ranging from ambient temperature to about 150"C or the reflux temperature of the chosen solvent.

The intermediates shown in Schemes I, II and 1 can be made according to generally accepted procedures. That is, the substituted benzoyl isocyanate 6 is replaced by the corresponding benzamide 5
From Speziale et al., Journal of Organic Medicine, Vol. 27, p. 6742 (
(1962) in which Xl, X, and X have the meanings given in formula (1).

Substituted aryloxyanilines 2 can be made according to Scheme V, which involves reacting a substituted aromatic alcohol 9 with chloronitrobenzene 8 in the following excess: Scheme V where Yl, mSR□ and 2 are Unless R1 is an acyloxyalkyl group, it has the meaning described in formula (1), provided that when Y□ is ortho to a nitro group, it is an alkyl group. Substituted aromatic alcohol 9
The reaction of and chloronitrobenzene 8 to give aryloxynitrobenzene 10 proceeds at elevated temperatures in the presence of a base in an inert solvent.

Suitable bases for this reaction are potassium carbonate, sodium hydride, potassium hydroxide, trichum hydroxide. Suitable solvents are toluene, dimeterformamide, dimethyl sulfoxide. The above transformations can be carried out in a biphasic reaction medium in the presence of a phase transfer catalyst.

The reduction of arylnitrobenzene 10 to aryloxyaniline 2 can be carried out in a hydrogen atmosphere using an unbound or homogeneous catalyst system. Suitable catalysts include palladium or platinum deposited on an inert support, a Raney nickel catalyst or an organic arthrocatalyst such as dichlorotris(triphenylphosphine)ruthenicum (Tetrahedron Letters, 216).
5 pages (1975)). The normally preferred conditions for these reductions are 40-1 hydrogen pressure in an inert solvent at ambient temperature.
Includes hydrogenation at 00 psi (2.8-7 to 9/Cm''). Solvents of choice include aromatic hydrocarbons such as toluene, alcohols such as ethanol, or esters such as acetate. This reduction can be carried out with chemical reductants such as transition metals or their salts in a solution of mineral acids. Usually tin or iron and their salts in hydrochloric acid are preferred. Dioxane or alcohols etc. Co-solvents may be added to improve the solubility of the reactants. Other suitable reducing systems use ammonium formate in methanol at room temperature in the presence of a palladium catalyst; Tetrahedron Letters, page 3415, (1984); Using hydrazine and a metal catalyst; Kacadian Journal Opchemistry, Vol. 58, p. 2565 (1960); Reduction with stannous chloride in ethanol: Tetrahedron Letters 8.
39 (1984).

Inciate 4 can be prepared by reacting substituted aryloxyaniline 2 with phosgene, or by reacting substituted aryloxyaniline 2 with carboni A/diimidazole.
648.72 (1961). Urea 7 can be obtained through the reaction of incyanate 4 with ammonium hydroxide or gaseous ammonia.

These reactions are shown in the above scheme (I). Here, Yl, ms几, and 2 have the meanings described in formula (1), except that R1 is not a carboxylic acid group or a hydroxyalkyl group. have

Substituted aryloxyaniline of type 2 can be obtained by herogenating aryloxyaniline 11 to the supernumerary scheme shown in the following scheme: R'' scheme: where Y, R, and ZU ( , n has a value of 0 or 1, and Y is chloro or bromo.As is clear from Scheme 2, at least one of the ortho positions with respect to the amine group of aryloxyaniline 11 One must be unsubstituted. Suitable solvents for this transformation include heroalkanes; aromatic hydrocarbons such as benzene; or polar protic solvents such as acetic acid. This can be carried out by exposure to chlorine or bromine at low temperature in a suitable solvent, or by treatment with N-herosuccinimide, preferably in benzene.The temperature required for the reaction depends on the nature of the substituents ¥8 and R. Although it varies depending on the temperature, it is usually in the range of 25° to 80°C.

Aryloxyanilines of type 11 can be prepared according to the method shown in Scheme 1 above, using chloronitrobenzene 12 as the electrophilic component in the camping reaction. Type 12 chloronitrobenzene is shown in the above plethora: R□ where R□ is not an acyloxyalkyl group (
Yl has the meaning described in formula (1), provided that Yo is alkyl when ortho to a nitro group, and n is 0 or has a value of 1.

Type 8 chloronitrobenzene precursors (e.g.
- Doki 16) from the corresponding nitroaniline to Miller, etc.
J, Med, Ohm, 2! + volume, 1086 pages (1
980) conducted by Sandm
ay@r).

Alternatively, chloronitrobenzene of type 16 can be made by nitration of chlorobenzene as exemplified by the synthesis of chloronitrobenzene 16 shown in the plethora of schemes ■ in F: Scheme ■ Chloronitrobenzene 16 of 5 -Methyl group tiF can be made into an acetal moiety according to a number of schemes (1): Scheme (2) where: alkyl, alkenyl, alkynino ν, poly8C77/! /Kill or go to Bo9 a Alknyl IfCf
I can do that. This is it, chloronitrotoluene 16
was treated with chromium dioxide in the presence of acetic anhydride and an acid catalyst to form a masked aldehyde
IV, 713) Ic. Exposure of a masked aldehyde to an alcohol in the presence of a catalytic amount of acid provides an example of a Type 8 functionalized chloronitrobenzene.

The manufacturing method for type 9 aromatic alcohol is Mitsche) L/
This is illustrated by the synthesis of 4-promo-2-fluorophenol from 2-fluorophenol using the procedure described by Mitehele et al. Another heptanolic intermediate, 2-promo-4-chlorophenol, is similarly obtained from 4-chlorophenol.

Another route to Type 2 aryloxyanilines, particularly aryloxyanilines 21, is shown in scheme Unless it is a group or a carboxylic acid group, it has the meaning described in formula (1), Y independently has the meaning described for Yl, and R1 is hydrogen, halogen, alkyl, noro-alkyl or bo9 Heroalkyl, 几 is hydrogen or halogen. This reaction is 7 yuram (Sehra)
mm) et al., Ann, vol. 740, p. 169 (197
Coupling of aminophenol 17 with 4-chloronitrobenzene 18 in the presence of a base to give 4-nitrophenoxyaniline 19 as described in 0).

Reaction of the amine group in 19 with cyclohexane-1,2-dicarboxylic anhydride provides diimide 20.

Nitro group reduction of the amine function, Tintomeyer octarogenation and deprotection affords nycyaniline 21 (R, is halogen). After reducing the nitro group in imide 2o, diazotization and reduction of the diazonium salt (J-A
m, 0bern.

Sac, (1952), vol. 74, p. 6o74,
Kai is Org.

React, (1944) Vol. 2, p. 262) gives aniline 21 (a, is hydrogen).

Amine phenols of type 17 are readily available, and the super-2.5-disubstituted phenol 22'ft nitration followed by halogenation and reduction of the nitro group as shown in the scheme of the aminophenol/L This product is made as shown in the synthesis of /25.
1 kL Dan Scheme■ Here, Y□ and 几□ are R□ an acyclic or cyclic acetal group, an acyclic or cyclic ditheoacetanosyl group, an acyclic or cyclic hemiteoacetal group, or Y has the meaning described in formula (1) except that it is not a carboxylic acid group.

is bromine or chlorine. This approach to intermediates 26 and 24 has been described by Albsrt and Sears (
Soars) is J, Am, Ohem, 8oe,
, Vol. 76, p. 4979 (f 954).

An alternative and supplementary approach to the amine phenol 17 is detailed in Scheme 1 of F: H Scheme 1) where Yl and 几IVit1) have the meanings described in formula 1) and Y, independently Yl has the meaning stated in . This involves reacting the trisubstituted phenol 26 with a diazonium salt made from sulfanilic acid to form the intermediate diazo compound 27, which is reduced to the aminophenol 17. The synthesis methodology used in this approach to aminophenol 17 is described by Payna and Welden in US Patent 3b752. a
This is what is described in No. 3a.

Another route to the aryloxyphenylbenzoyl urea contained in formula (1) is to reduce the nitro group to benzoyl isocyanate 6 after binding the acetal moiety-containing azyloxynitrobenzene with 14 functional groups (Scheme Xl). Including making a ring.

Thus, acetals can undergo acetal exchange to form aryloxynitroacetals upon exposure to alcohol in the presence of catalytic amounts of acid. Diaryloxyphenylbenzoyl urea acetal is obtained by reduction of the nitro group and conversion of the generated aniline to benzoyl isocyanate 3.

(a) 11 Mu Flea O
Xl, X3, X8, Y□ and 2 have the meanings described in formula (1), Y independently has the meaning described for Yl, and 几 is alkyl, alknyl, polyhaloalkyl or Can be made into polyheroalpnyl,
Q can be an acyclic diteoacetal, a cyclic diteoacetal, or a cyclic hemiteoacetal moiety.

Hydrolysis of the acetal to the corresponding aldehyde proceeds in an aqueous acid solution. This aldehyde is reacted with a hexa-ol, di-t-ol or mercapto alcohol in the presence of an acid catalyst to form an acyclic ditheoacetal, respectively.
to a cyclic diteoacetal or the corresponding nitroether having a cyclic hemiteoacetal moiety. The nitro group is chemically reduced to the corresponding aniline, which is reacted with a substituted benzoyl isocyanate to form the functionalized benzoyl urea. Alternatively, the aldehyde moiety is oxidized to a carboxylic acid derivative, followed by esterification, reduction of the nitro group, and cambling with benzoyl isocyanate to form a benzoyl urea having an ester moiety as a bond.

1-(4-aryloxyphenyl) described by the present invention
-6-benzoyl urea mineral In addition to exhibiting significant properties as a precious drug, it can also serve as a key intermediate in the synthesis of a number of other novel insecticidal compounds as listed in section f.

Here, X□, X*, Y□, and Zd have the meanings described in formula (1); Y independently has the meanings described for Y; It is an alkyl, herogen, nitro, cyano, or carboxylic acid ester group, and Ql is (FltO), PO, Ph, or hydrogen mineral.

Mild acid hydrolysis of aceter A72B yields aldehyde 2
9, and this is John's reagent (Jon@sReagan).
t) to form a Type 60 acid. 29
by polyhydride reduction to obtain hydroxymethe f) ν compound 31
and a reaction involving 29 and reagent 33 gives an olefin of type 32.

The compounds contemplated in this invention can be used by methods known in the art as insecticides. Eocicidal compositions containing the compound prior to activation usually include a carrier and/or diluent, either as a liquid or a solid.

Suitable liquid diluents or carriers include water, petroleum distillates or other liquid carriers with or without surfactants. Liquid concentrates contain one of these compounds
It can be made by dissolving the poison in a non-toxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimef)L/formamide and dispersing the poison in water with the aid of suitable surfactant emulsifiers and dispersants. .

The selection of dispersants and emulsifiers and their amounts to be used is directed by the nature of the composition and the ability of the agent to promote dispersion of the toxicant. It is usually desirable to use the smallest amount of agent possible consistent with the desired distribution of the toxin in the spray so that after the toxin has been applied to the plant, rain does not re-emulsify the toxin and wash it away from the plant. . Nonionic, anionic or cationic dispersants and emulsifiers can be used, such as condensation products of alkylene oxides with phenols and organic acids, alkylaryl sulfonates, complex ether alcohols, quaternary ammonium compounds, etc. .

For preparing wettable powders or powder or granular compositions, the active ingredient is dispersed in suitably divided solid carriers, such as clay, talc, benthite, clay, fuller's clay, etc. In formulating the wettable powder, the above-mentioned dispersant and lignosulfonate can be included.

The required amount of the poison contemplated by the present invention is
It can be applied with ~200 gallons or more of liquid carrier and/or diluent, or with about 5 to 500 gallons of inert solid carrier and/or diluent. Concentrations in liquid concentrates usually range from about 10 to about 95 weight units, and concentrations in solid formulations range from about α5 to about 90 weight units.

Satisfactory sprays, powders or granules for general use are
Contains about 7-15 bonds of active poison.

Good drugs contemplated by the present invention prevent the plants or other materials to which they are applied from being attacked by insects, and have relatively high residual toxicity. When used on plants in an amount sufficient to kill or exterminate pests, the pesticides do not burn or harm the plants, and they do not cause washing-off caused by rain, decomposition by ultraviolet rays, oxidation, or resistant to weathering, including hydrolysis in the presence of moisture, or at least decomposition, oxidation, and hydrolysis that significantly reduces the desired insecticidal properties of the poison or imparts undesirable properties to the poison, such as nuisance. has a high safety factor. Because the poison is extremely chemically inert, it can now be compatible with virtually all other elements of the spray schedule.
And it can be used in soil, plant seeds or roots without harming them.

If desired, mixtures of active compounds, as well as combinations of the active compounds of the invention with other biologically active compounds or ingredients, can be used.

The following examples illustrate methods used to prepare intermediates and compounds of the invention. Chemical shifts for NMR spectroscopy are reported in parts per million downfield from TMS.

Example A A 5 lindre triturator reaction flask equipped with an internal thermometer and a mechanical stirrer was charged with 44-dichloro-2,5-enemethel-1-nitrobenzene (200 grams, α909 moles). Then acetic anhydride was added. Complete dissolution of the solid nitrobenzene starting material was effected by stirring and gentle warming with a heat gun. The mixture was then cooled to a temperature of 09-10° C. and sulfurized #I (20 milliliters) was added dropwise. A solution of chromium trioxide was then made into an excess of: Chromium trioxide (245.6 grams, 2.46 moles) was added to liters of acetic anhydride in an Erlenmeyer flask with stirring at ambient temperature. added. This bath liquid is then added to the paste-like reaction mixture for 2 hours while keeping the temperature below 10°C.
It dripped over time. The mixture was then allowed to warm to room temperature and stirred for 15 hours. The mixture was poured into cold water (16 liters) and allowed to stand overnight. The water was decanted and the residue was dissolved in ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate, prine, dried over sodium bicarbonate, washed once, and concentrated under reduced pressure to give 200 g of a brown oil (
65%). 5-bisacetoxymethyl-4-dichloro-2-methyl-1-nitrobenzene (47.9 g, α142 mol, 16%) by recrystallization from hexane, mp 99-107. C. Elemental analysis of the cream powder showed the following: Analysis: 01.Hl, 01.NO.

Calculated: 0.42.88; H, 530; N, 4.17 Actual measurement: 0,42.62: HS549; N5404 Example B 5-bisacetoxymethyl-3, prepared in Example B
4-dichloro d-2-methyl-1-nitrobenzene (47
, cp rubrum α143 moa v) in methanol (14 liters) was added concentrated sulfuric acid (10 drops). The solution was heated at reflux overnight, cooled, quenched with saturated sodium bicarbonate solution, and concentrated in vacuo F. When most of the methanol was removed, engineered tyl acetate was added, and the organic layer was diluted with water.
Washed with brine, dried with sodium 4Jlic acid,
Concentrate in vacuo to give 44-diclodyl-dimethoxymer6-1-nitrobenzene (68.7 grams, 0.158
mmol, 97%) as a brown oil. Elemental analysis of the brown oil showed a Do period: Analysis 20□. H1□01. No.

Calculation: 0.42.88; H2S, 96 iN, 5
．． 00 actual measurement: C14507; H, 593, N15.36
Example C 150 grams of the 4-dichloro-5-dimethoxymethyl-2-methyl-1-nitrobenzene prepared v14 in Example B was placed in a 600 ml three-bottle round bottom flask equipped with a condenser, nitrogen inlet and magnetic stirrer. , 26.78m
mole) and 2-bromo-4-chlorophenol (6,6
7')” rum, 32, 14 mmol) and potassium rum carbonate (
7.40 g, 556 mmol) and dimethylbormamide (60 ml) were charged and the mixture was heated at a temperature of 110° C. overnight. Let the mixture cool;
The mixture was transferred to a 1 liter round bottom flask, and almost every fl of dimethylformamide was distilled off under reduced pressure. Then toluene and 5% potassium hydroxide solution were added. The organic layer was separated, washed successively with 5% catholicum hydroxide, water, brine, dried over magnesium sulfate, and concentrated in vacuo to yield a brown solid.

Recrystallization from hot medilene chloride-methanol
2-bromo-4-chlorophenoxy7)-5-gloro-5
-Dimethoxymeca A/-2-methyl-1-nitrobenzene (4.78 grams, IQ, 60 mmol, 40%) was produced as a crystalline powder with a melting point of 116°-117°C. Elemental analysis of the crystalline powder showed the following: Analysis: OL, J401. BrN0° calculated, 0.42.6 (J: H, 515; NS! 11 actual measurement 20, 42.93; H2S, 22; N, 3.05 Example D 4-(2-bromo 4-chlorophenoxy )-6-Chloro-5-dimethoxymethyl-2-methylaniline In a Parr bottle, 4-(2
-bromo-4-chlorophenoxy)-6-chloro-5-
methoxymether-2-methyl-1-dibenzene (
A 5:1 mixture (120 milliliters) of 4.18 grams, 927 mmol/I/) and hydrene, ether acetate was charged. The reaction vessel was then thoroughly burnt with nitrogen and 5% white #t on carbon (15 grams) was added immediately after purging. Add the mixture to 40-50 pii (28
The mixture was then passed through the back of a Cephite band and concentrated in vacuo to give a 4-( 2-Bromo-4-chlorophenoxy)-6-chloro-5-dimethoxymethyl-2-methylaniline was produced in quantitative yield. Elemental analysis showed F: Analysis: 0., H□, Br01. No.

Calculation: 0.45.64; H, 583; NS3,55
Disaster prediction: 0.45.94; If, ri, 91; N, i
2B Example E Method In a 500 ml round bottom flask equipped with a magnetic stirrer, heating mantle, reflux, condenser, and nitrogen inlet, 6-
Chloro-4(2,4-iyfluorophenoxy)-5-
Dimethoxymethyl-2-methylnitrobenzene (12,
0 grams, 32.11 mmol). Next, acetic acid (128 mm, 99 tons) was added with stirring, followed by water (52 mm, 99 tons). The heterogeneous mixture was heated to reflux for 1 hour and poured into water (soo milliliters). The mixture was extracted with toluene and the organic layer was washed with saturated potassium bicarbonate and brine, dried over potassium sulfate, filtered and concentrated in vacuo to give 6-chloro-4-(2,4
-difluorophenoxy)-5-formyl-2-methylnitrobenzene (1α1 g, 6α82 mmol, 96
．． 9%) as a yellow solid with a melting point of 150°-156°C. Elemental analysis of the yellow solid showed the following: min.
27 actual measurement: 0.5131; H12, 47iN, 4.
Example 19 F - Preparation of 1,6-diteolane Magnetic stirrer, heating mantle, reflux condenser, nitrogen inlet, 1
3-chloro-4-(2,4-difluorophenoxy)-5-formyl-2- was placed in a 250 ml round bottom reaction flask equipped with a gas outlet tube connected to a trap containing 0% aqueous catolicum hydroxide solution. Mecalu 1-nitrobenzene (7.0 grams, 21.36 mmol) L/) was added as a slurry in toluene (46 milliliters). Then ethanedithiol (2.21 grams, 24
．． 0 mmol) and p-toluenesulfonic acid-hydrate@(
0.4 grams, 2.1 mmol) was added and the mixture was heated at reflux for 60 minutes. Then add Dean Stark (
A Dean-8t wrap was applied and reflux continued for an additional 35 minutes. The mixture was allowed to stand overnight at room temperature under nitrogen* atmosphere, diluted with toluene, washed with saturated sodium charcoal and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2-(3-chloro-2
-(2,4-difluorophenoxy)-4-methyl-5
-nitrophenyl)-t3-diteolane (s, 50 grams, 20.55 mmol, 96.2%) with a melting point of 114°
-117'C as a pale yellow solid. Elemental analysis of the yellow solid showed F: Analysis: C□,,H,,01li', No, 8° Calculation:
0.47.58 iH, 5, oO; N, 547 actual measurement: 0
．． 47.72; H, 2,97; N, 3.39-q
- The 2-(3-chloro -2-(2,4-
difluorophenoxy)-4-methyl-5-nitrophenyl)-1,s-diteolane (8.0 grams, 19.
81 mmol) was added as a slurry in ethanol (40 milliliters). Tin (I) chloride dihydrate (2
2.3 s g, 99.05 mmol) were added and the mixture was heated for 1 hour at a temperature of 62-78°C. The mixture was allowed to cool to room temperature and then poured into ice water (400ml).
poured into the. After the ice melted, the pn of the mixture was adjusted to pH 7 with 5% aqueous catolicum bicarbonate. The mixture was extracted with ethyl acetate (2X). The organic layer was washed with brine, dried over sodium sulfate, filtered and purified under vacuum F to give 2-(5-amino-6-chloro-2-(2
,4-difluorophenoxy)-4-methylphenyl)
-1,3-9r oran (6,87 g, 18.38 m
molar, 92.7%) as a viscous oil. '11-N
MR analysis showed F: 'H-NMR (ODOI,
): 67.43-6.50 (m, 31■), 6, 2
2 (s, IH), 5.85 (m, IH)
, 180 (brl, 2H), 172-106 (r
n, 4H), 2.24 (m.

3H).

Preparation method of Example 1 Into a round-bottomed reaction flask, 3-
Chloro-4-(2,4-dichlorophenoxy)-5-dimethoxymethyl-2-methylaniline (8.90 grams, 2566 n1 mole) and toluene (45 milliliters) were charged. The mixture was warmed to achieve complete dissolution of the aniline and then purged with nitrogen. Next, pure 2
,6-cyfluoropenzoyl isocyanate (4,33
grams, 25 and 65 mmol/I/) were added to the reaction mixture via syringe.

The product benzoylurea precipitated almost immediately and a mild exotherm occurred. The product was filtered once and washed with cold ether to give 1-(3-chloro-4-(2,4-dichlorophenoxy)-5-dimethoxymecal-2-methylphenyl-
5-(2,6-difluorobenzoyl)urea (1190
grams, 2126 mmol, 90%), melting point 190-19
It arose as a crystalline powder at 1°C. Elemental analysis of the crystalline powder showed the following: Analysis: C□H,,01,F,N,O.

Calculation: 0.5t50; H, 3,42; N, 5.01 Actual measurement 20, 51.45; H, 555, N, 4.90 Example 2 Round bottom reaction flask equipped with magnetic stirrer, reflux condenser 1-(6-chloro-4-(2,
4-dichlorophenoxy)-5-dimethoxymethyl-2
-Methylphenyl)-5-(2,6-difluorobency/L/)urea (1α6 grams, 18.94 mmol) and a 5:1 mixture of acetic acid:water (200 mm!J!1 torr) were added. Ta. The heterogeneous mixture was heated to reflux for 1 hour, then cooled to room temperature. Water (200 milliliters) was added to the reaction mixture and the product was washed with water and cold methanol, dried in a vacuum oven and 1-(3-chloro-4-(2,
4-dichlorophenoquine)-5-formyl-2-methylphenyl)-3-(2,ts-difluorobency/I
/) Urea (900 grams, 17.52 mmol, 92%
) was produced as a white powder with a melting point of 222°-225°C.

Elemental analysis of the white powder showed F: Analysis: 0□H1,01,F,N,O.

Calculation: 0.51441H, 2,55+N, 5.45 Actual measurement: 0.5t57 +H, 2,54IN, 5.61 Preparation method 0B of Example 3 1-(6-chloro-4-(2,4
-dichlorophenoxy)-5-formyl-2-methy/I
/phenyl)-5-(2,6-difluorobenzoyl)
Powdered potassium borohydride (150 mg, 189 °C mo/l) was added to a solution of urea ('zoo grams, 5-89 nmol) in methanol/l/l (48 milliliters).
I/) was added. Tetrahydro7lane (20 milliliters) was then added and the reaction mixture was heated at ambient temperature for 1 hour.
It was stirred overnight. Then add additional sodium borohydride (
150 mg, 589 tamol) were added and the reaction mixture was stirred for α5 hours. The excess sodium borohydride was destroyed and the product precipitated by adding 5% sulfuric acid (100 μl). The precipitated product was collected at 7 fr.
collected in a funnel and washed with water and ether to give 1-(6-chloro-4-(2,4
-dichlorophenoxy)-5-hydroxymefA/-2
-methylphenyl)-5-(2,6-difluorobenzoyl)urea (750 mg, 145 mmol, 37%
) was given. Elemental analysis showed the following: Analysis: 0□■□, 01. F, N, O.

Calculation 20, 5124; M, 2.95; N, 5.
45 actual measurement 20, 5'L02+H1500iNS4.97
Example 4 1-(3-chloro-4-(2,4
-dimethylphenoxy)-5-formyl-2-methylphenyl)-3-<2.6-di7/I/olobenzoy A/
) urea (120 grams, 2.50 mmol) in acetone (
John's Reagent T in a magnetically stirred solution in
199 tons was added. The mixture was stirred for 15 hours and additional John's reagent (to microliters) was added post-mortem. The mixture was stirred for 15 minutes, quenched with saturated sodium sulfite solution (5 milliliters), and concentrated under reduced pressure f. Add chlorine acetate to the residue, filter the organic layer, wash with water and brine, dry with 1" thorium,
Concentration in vacuo gave the crude product as a highly insoluble white powder. This material was titrated with 1=1 hechitin:ethel acetate and had a melting point of 237°-238°C.
Carboxy-6-chloro-4-(2,4-dimethylenoxy)-2-methylphenyl)-3-(2,6-cyfluorobenzoy A/)urea (560 mg, t1
4 mmol, 46%). Elemental analysis showed )'; Analysis: Ota Hl, 01 F, N,
O.

Calculation 20, 5B, 97 ;H,! L92; N, 5.
73* Measurement 2 〇, 5B, 73; H, 5
,94;N, 5.58 Example 5 Into a 100 ml round bottom reaction flask equipped with a magnetic stirrer was added the 1-(3-chloro-4
-(2,4-dimethylphenoxy)-5-formyl-2
-methylphenyl)-6-(2,6-difluorobenzoyl)urea (zxo Durham, 4.86 mmol) and (
Add 2-methquine-2-oxoether)triphenylphosphonium 10mide (2.22 grams, 5.54 mmol) and tetrahydrofuran (20.9 liters). This heterogeneous mixture was added to ta-diazabicyclo(5,4,
0) Undeca-couene (DBU) (z63 mg, 5.Q I 111 mole) was added. Mixing method 5
The mixture was stirred for an hour, filtered, and concentrated under reduced pressure. Flange column chromatography (hexane: ether acetate) 5
:1) is 1-(3-chloro-4-(2,4-dimecaleneoxy)-5-(2-methoxycarbonyl-1-ethynyl)-2-methylphenyl with a melting point of 198°-205"C )-3-<2.6-difluorobenzoyl) urine 51(
ts Durham, 2.84 rnmol, 58%). Elemental analysis showed F: Analysis: 0. ,,H,,OIF
, N.O.

Calculation: 0.61.51, H, 4, 38:N, 5.50
Actual measurement: 0.6t25; IC4,38iN, 5.14
Examples 6-38 In a manner similar to that used in the previous examples, other urea compounds were made using one of the previously disclosed synthetic schemes. Identification of substituents in the general formula and analytical data are listed in Table ■ of F and Summer: Naka Uchi Q Q Insect Naka Cocoon
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Around 01ktlktC1 Rumor Rumor Some representative examples of the novel compounds of the present invention include caterpillars (order eaterpiformes) and beetles. An evaluation was conducted to determine their insecticidal activity against insects.

A suspension of the test compound was made by dissolving 100 iu grams of the compound in 15 ml of dimef/L/formamide and then adding 8.5 iu of acetone containing 0.25 k of alkylphenoxypolyethoxyethanol surfactant as an emulsifier or dispersant. Added milliliters. 30% of the resulting solution
Approximately 40 milliliters of a suspension containing finely divided compounds in 99 liters of water. The stock suspension thus produced contained 2.5% by weight of the compound. Test concentrations in parts per million by weight used in the tests described hereinafter were obtained by appropriate dilution of the stock suspension with water. Suspensions were obtained using sonication when necessary. The test procedures were as follows: Tendergreen bean plant (Tendergreen b)
eanplant) at a temperature of 80°±5”F (2&
ipodopt@ra@rldanl grown at 7°±28°C) and 50±5% relative humidity.
a, (Oram+)) larvae constituted the test insects.

The test compound is prepared by diluting with water as a storage suspension and containing the test compound at the concentrations listed in the table below (parts of test compound per million parts of final formulation). did. Place stingy-planted Tengou green bean plants of standard height and age on a rotating turn-cheep bush and
Formulation 1 of the test compound was sprayed using a Vilbims spray gun set at an air pressure of Q pslg (2,8 kg IC1'G). This application lasted 25 seconds and was enough to wet the plants and cause them to run off. As a control, infested plants were also sprayed with 100 L of a water-acetone-emulsifier solution containing no test compound. When dry, the pairs of leaves were separated and each leaf was placed in a 9 cm veterinary dish lined with moist filter paper. Five randomly selected larvae were placed in each dish and the dishes were closed. Attach the label to the closed plate, and
It was kept at °~ss'F (27'-29°C) for 5 days.

The larvae were able to easily consume the entire leaf within 24 hours, but no further food was added. Larvae that were unable to move the length of their bodies even when stimulated by pecking were considered dead. The % mortality was recorded for the concentration level of Nasana.

IiiipHachna varivesti grown on tender green bean plants at a temperature of 80° ± 51 and a relative humidity of 50 ± 5%.
g.

The test insects were 6th instar larvae of A. Mulg.).

The test compound was formulated by diluting the stock suspension with water to give a suspension containing the test compound at the concentrations listed in Table F (parts of test compound per million parts of final formulation). Tengu green bean plants of standard height and age were placed on a rotating turntable and sprayed with 100 milliliters of the test compound formulation using a Tobilpis O spray gun set at an air pressure of 40 psig. This application is 2
It lasted 5 seconds and was enough to wet the plants and cause a runoff. As a control, a 100ml water-acetone-emulsifier solution containing no test compound was also used. I liter was sprayed on the infested plants. When dried, the pairs of leaves were separated and each was placed in a 9 cm petri dish moistened and lined with silica paper. Five randomly selected larvae were placed in each dish and the dishes were closed. Closed nine dishes were labeled and kept at a temperature of 806±5°F for 5 days. The larvae were able to easily consume the leaves within 24-48 hours, but no further food was added. Larvae that were unable to move the length of the body even at nine o'clock upon stimulation were considered dead.

Tobacco moth (Helio
this vlresaenm, ? +) second instar larva (
yIL (approximately 2.5w9) and Octopus moth (Helio
thiszea, (Boddfe)) second instar larva (
'iL approximately 2.5719) constituted the test bed.

Same method as above, except that cotton trees were replaced with pods j1
The treated and dried cotton leaves were placed in 9 veterinary dishes and organized into groups of 10 dish sets. One randomly selected larva was placed in each dish of a set of 10 dishes and the dishes were closed. Attach the label to the closed pan and hold it at 80°.
I kept it on soil 51 for 5 days. Larvae that were unable to move the length of their bodies even when stimulated were considered dead. Mortality was recorded for various concentration levels.

The biological properties of some representative examples of the compounds of the present invention are listed in Sections 4m and 2 below.

Table I I A
A2 A
05 A
A4 A
, 07
A A8
A A9
A AlQ
A).

11 people A
l1. 71
M13 A
A14 A
A15 A
A16 A
Mu17 ^
A18 A
B19 A
A20
A A21
A).

22 A
7123A
A25 A
A26 A
Person 27 A Person 28 A
A29 A
people, 50
A A51
A A62
people 55 people
A M54
Mmu 35
A″ A・56
A A37
A A38
B 0(
1) Southern armyworm (2) Mexican spotted tent beetle (3) Code: A-71-kills 100% B-31-kills 70% 0=Ω-kills 60% Tested at 500 ppm Ecchi in the example number, Biresun Ecchi. There1 person
Muro A
A8
Person -11A
- 21A - 26A - 28 people A 29 B A (Re)
Code 2 Aヰ71-kills 100% B-51-kills 70%0-kills 0-30%Illustrate the invention by the previous example9, but consider that the invention is limited to the substances used in the example Rather, the invention encompasses the general area disclosed herein above.

Various modifications and embodiments can be made without departing from the spirit and scope of the invention.

Claims (1)

[Claims] 1. A compound of the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 represents halogen; X_2 and X_3 independently represent hydrogen or halogen;
Y_1 independently represents halogen, alkyl, alkoxy, nitro or cyano; m has a value of 0 to 2; R_1 is an acyclic or cyclic acetal group, an acyclic or cyclic dithioacetal group, an acyclic Formula or cyclic hemitioacetal group, aldehyde group, carboxylic acid group or its ester derivative, hydroxyalkyl group, alkoxyalkyl group,
represents an acyloxyalkyl group, an alkenyl group, or an alkylcarbonyl group, provided that when R_1 is a carboxylic acid group or its ester derivative, m has a value of 2, and R_1 is in the 2-position or Z is a substituted or unsubstituted, saturated or unsaturated monocyclic ring system; or (ii) a substituted or unsubstituted, saturated or unsaturated ring system; Bicyclic fused rings, wherein at least one ring is a 6-membered unsaturated carbocyclic ring and the second ring is a 5- or 6-membered carbocyclic ring or a carbonyl group or one or two rings. a 5- or 6-membered heterocyclic ring that can contain oxygen or sulfur atoms in any combination). 2. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 1, and Y_2 is independently described for Y_1. R_2, R_3
, R_4 is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl). 3. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, R_1 are the first claims
(Y_2 independently has the meaning described for Y_1, and R_2 and R_3 are independently hydrogen, halogen, alkyl, haloalkyl, or polyhaloalkyl) Compounds described. 4. The following formula: ▲ Numerical formula, chemical formula, table, etc. or polyhaloalkyl) according to claim 1. 5. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 1, and Y_2 is independently Y_1
R_2, R_3, R_4
is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 6. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 1, and Y_2 is independently Y_1.
R_2, R_3, R_4
is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 7. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 1, and Y_2 is independently Y_1
A compound according to claim 1, having the meanings given for R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 8. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 1, and Y_2 is independently Y_1
A compound according to claim 1, having the meanings given for R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 9. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 1, and Y_2 is independently Y_1.
2. A compound according to claim 1, having the meanings given for R_6, R_7 are independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 10. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 1, and Y_2 is independently described for Y_1. R_2, R_3
is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 11. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1, R_1 are as shown in claim 1, and Y_2 is independently described for Y_1. 2. A compound according to claim 1, having the following meaning: R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 12. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 1, and Y_2 is independently described for Y_1. A compound according to claim 1, having the meaning: R_5 is hydrogen, alkyl or halogen. 13. The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 1, and Y_2 is independently described for Y_1. The compound according to claim 1, having the following meaning: R_6 and R_7 are independently hydrogen, alkyl or halogen. 14. Z is the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Selected from substituted or unsubstituted systems having ▲ mathematical formulas, chemical formulas, tables, etc. A compound according to claim 1. 15. R_1 is an acyclic acetal group having the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, each R is independently alkyl, alkenyl, alkynyl, polyhaloalkyl, or polyhaloalkenyl) Claim 1
Compounds described in Section. 16. An acyclic dithioacetal group in which R_1 is the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, each R is independently alkyl, alkenyl, alkynyl, polyhaloalkyl, or polyhaloalkenyl) The compound according to claim 1, which is 17. The compound according to claim 1, wherein R_1 is a cyclic acetal group having the following formula: ▲A mathematical formula, a chemical formula, a table, etc.▼ (wherein n is a value of 2 or 3). 18. The compound according to claim 1, wherein R_1 is a cyclic dithioacetal group having the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein n is a value of 2 or 3) . 19, R_1 is a cyclic hemitioacetal group having the following formula: ▲A mathematical formula, a chemical formula, a table, etc.▼ (wherein n is a value of 2 or 3) Compound. 20. The compound according to claim 1, wherein R_1 is a carboxylic acid ester group having the following formula: -CO_2R (wherein R is alkyl, alkenyl, alkynyl, polyhaloalkyl, or polyhaloalkenyl). 21. The compound according to claim 1, wherein R_1 is an acyloxyalkyl group having the following formula: -OH_2OCOR (wherein R is alkyl, alkenyl, alkynyl, polyhaloalkyl or polyhaloalkenyl). 22. The compound according to claim 1, wherein R_1 is an alkoxyalkyl group having the following formula: -CH_2OR (wherein R is alkyl, alkenyl, alkynyl, polyhaloalkyl or polyhaloalkenyl). 23. A patent where R_1 is an alkenyl group having the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R' and R'' are independently hydrogen, halogen, nitro, cyano, or ester group) Compound according to claim 1. 24,1-[3-chloro-4-(2,4-dichlorophenoxy)-5-dimethoxymethyl-2-methylphenyl]-3-(2,6-difluorobenzoyl) ) The compound according to claim 1, which is urea. 25,1-[3-chloro-4-(2,4-dichlorophenoxy)-5-formyl-2-methylphenyl]-3-
The compound according to claim 1, which is (2,6-difluorobenzoyl)urea. 26, 1-[3-chloro-4-(2,4-dichlorophenoxy)-5-hydroxymethyl-2-methylphenyl]-3-(2,6-difluorobenzoyl)urea Claim 1 Compounds described in Section. 27,1-[5-carboxy-3-chloro-4-(2,
4-dimethylphenoxy)-2-methylphenyl]-3
-(2,6-difluorobenzoyl)urea. 28, 1-[3-chloro-4-(2,4-dimethylphenoxy)-5-(2-methoxycarbonyl-1-ethenyl)-2-methylphenyl]-3-(2,6-difluorobenzoyl)urea The compound according to claim 1, which is 29, Claim 1 which is 1-[3-chloro-4-(2,4-dichlorophenoxy)-5-dimethoxymethyl-2-methylphenyl]-3-(2,6-dichlorobenzoyl)urea Compounds described in Section. Claim 1 which is 30, 1-[3-chloro-4-(2,4-dimethylphenoxy)-5-dimethoxymethyl-2-methylphenyl]-3-(2,6-difluorobenzoyl)urea Compounds described in Section. 31, Claim 1 which is 1-[3-chloro-4-(2,4-dimethylphenoxy)-5-dimethoxymethyl-2-methylphenyl]-3-(2,6-dichlorobenzoyl)urea Compounds described in Section. 32, Claims that are 1-[3-chloro-4-(2-bromo-4-chlorophenoxy)-5-dimethoxymethyl-2-methylphenyl]-3-(2,6-difluorobenzoyl)urea A compound according to item 1. 33, Claims that are 1-[3-chloro-4-(2-bromo-4-chlorophenoxy)-5-dimethoxymethyl-2-methylphenyl]-3-(2,6-dichlorobenzoyl)urea A compound according to item 1. 34, 1-[3-chloro-4-(4-chloronaphthoxy)-5-dimethoxymethyl-2-methylphenyl]-3
-(2,6-difluorobenzoyl)urea. 35, 1-[3-chloro-4-(4-chloronaphthoxy)-5-dimethoxymethyl-2-methylphenyl]-3
The compound according to claim 1, which is -(2,6-dichlorobenzoyl)urea. 36,1-[3-chloro-4-(2,4-dichlorophenoxy)-5-(1,3-dithiacyclopentane-2-
2-methylphenyl]-3-(2,6-difluorobenzoyl)urea. 37, 1-[3-chloro-4-(4-chloronaphthoxy)-5-(1,3-dithiacyclopentan-2-yl)
The compound according to claim 1, which is -2-methylphenyl]-3-(2,6-difluorobenzoyl)urea. 38, 1-[3-chloro-4-(2,4-difluorophenoxy)-5-(1,3-dithiacyclopentane-2
The compound according to claim 1, which is -yl)-2-methylphenyl]-3-(2,6-difluorobenzoyl)urea. 39, 1-[3-chloro-4-(2,4-dichlorophenoxy)-2-methyl-5-(3-oxa-1-thiacyclopentan-2-yl)phenyl]-3-(2,6 −
Claim 1 which is difluorobenzoyl) urea
Compounds described in Section. 40. An acceptable carrier and an insecticidal effective amount of a compound of the following formula: ▲Mathical formula, chemical formula, table, etc.▼ (In the formula, X_1 represents a halogen; X_2 and X_3 independently represent hydrogen or a halogen. ;
Y_1 independently represents halogen, alkyl, alkoxy, nitro or cyano; m has a value of 0 to 2; R_1 is an acyclic or cyclic acetal group, an acyclic or cyclic dithioacetal group, an acyclic Formula or cyclic hemitioacetal group, aldehyde group, carboxylic acid group or its ester derivative, hydroxyalkyl group, alkoxyalkyl group,
represents an acyloxyalkyl group, an alkenyl group, or an alkylcarbonyl group, provided that when R_1 is a carboxylic acid group or its ester derivative, m has a value of 2, and R_1 is in the 2-position or Z is a substituted or unsubstituted, saturated or unsaturated monocyclic ring system; or (ii) a substituted or unsubstituted, saturated or unsaturated ring system; Bicyclic fused rings, wherein at least one ring is a 6-membered unsaturated carbocyclic ring and the second ring is a 5- or 6-membered carbocyclic ring or a carbonyl group or one or two rings. a 5- or 6-membered heterocyclic ring which can contain oxygen or sulfur atoms in any combination. 41. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 40, and Y_2 is independently Y_1 R_2, R_
3. The agricultural chemical composition according to claim 40, wherein R_4 is independently hydrogen, halogen, alkyl, haloalkyl, or polyhaloalkyl. 42. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, R_1 are
As shown in item 0, Y_2 independently has the meaning described for Y_1, and R_2 and R_3 independently represent hydrogen,
41. The agrochemical composition according to claim 40, which has the following: halogen, alkyl, haloalkyl, or polyhaloalkyl. 43. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1 and , haloalkyl or polyhaloalkyl) according to claim 40. 44. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 1, and Y_2 is independently Y_1
R_2, R_3, R_4
is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 45. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 40, and Y_2 is independently Y_
R_2, R_3, R_
41. The agricultural chemical composition according to claim 40, wherein 4 is independently hydrogen, halogen, alkyl, haloalkyl, or polyhaloalkyl. 46. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 40, and Y_2 is independently Y_
41. Agrochemical composition according to claim 40, having the meanings given for 1 and R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 47. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 40, and Y_2 is independently Y_
41. Agrochemical composition according to claim 40, having the meanings given for 1 and R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 48. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 40, and Y_2 is independently Y_
41. Agrochemical composition according to claim 40, having the meanings given for 1 and R_6, R_7 are independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 49. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 40, and Y_2 is independently Y_1 R_2, R_
41. The agrochemical composition according to claim 40, wherein 3 is independently hydrogen, halogen, alkyl, haloalkyl, or polyhaloalkyl. 50. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, X_3, Y_1, R_1 are as shown in claim 40, and Y_2 is independently 41. Agrochemical composition according to claim 40, having the meanings given for R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 51. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 40, and Y_2 is independently Y_1 41. Agrochemical composition according to claim 40, having the meanings given for R_5 and R_5 is hydrogen, alkyl or halogen. 52. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 40, and Y_2 is independently Y_1 R_6, R_
41. The agricultural chemical composition according to claim 40, wherein 7 is independently hydrogen, alkyl or halogen. 53. A compound of the following formula in an effective amount to kill insect pests: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1 represents halogen; X_2 and X_3 independently represent hydrogen or halogen;
Y_1 independently represents halogen, alkyl, alkoxy, nitro or cyano; m has a value of 0 to 20; R_1 is an acyclic or cyclic acetal group, an acyclic or cyclic dithioacetal group, an acyclic or cyclic hemitioacetal group, aldehyde group, carboxylic acid group or ester derivative thereof, hydroxyalkyl group, alkoxyalkyl group,
represents an acyloxyalkyl group, an alkenyl group, or an alkylcarbonyl group, provided that when R_1 is a carboxylic acid group or its ester derivative, m has a value of 2, and R_1 is in the 2-position or Z is a substituted or unsubstituted, saturated or unsaturated monocyclic ring system; or (ii) a substituted or unsubstituted, saturated or unsaturated ring system; Bicyclic fused rings, wherein at least one ring is a 6-membered unsaturated carbocyclic ring and the second ring is a 5- or 6-membered carbocyclic ring or a carbonyl group or one or two rings. a 5- or 6-membered heterocyclic ring which may contain oxygen or sulfur atoms in any combination. 54, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 53, and Y_3 is independently R_2, R_
54. The method of claim 53, wherein R_4 is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 55. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, R_1 are
As shown in Section 3, Y_2 independently has the meaning described for Y_1, and R_2 and R_3 independently represent hydrogen,
54. The method of claim 53, wherein the halogen, alkyl, haloalkyl or polyhaloalkyl. 56, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 and , haloalkyl or polyhaloalkyl). 57, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 53, and Y_3 is independently Y_
R_2, R_3, R_
54, wherein 4 is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 58, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 53, and Y_2 is independently Y_
R_2, R_3, R_
54, wherein 4 is independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 59, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1 are as shown in claim 53, and Y_1 independently represents Y_
54. The method of claim 53, wherein R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 60. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, X3, Y_1 are as shown in claim 53, and Y_3 is independently Y_1
54. The method of claim 53, wherein R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 61. The compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_1, X_3, Y_1 are as shown in claim 53, and Y_2 is independently Y_
54. The method of claim 53, wherein R_6, R_7 are independently hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 62, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 53, and Y_2 is independently Y_1 R_2, R_
54. The method according to claim 53, wherein 3 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 63, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, Y_1, R_1 are as shown in claim 53, and Y_2 is independently 54. The method of claim 53, wherein R_5 is hydrogen, halogen, alkyl, haloalkyl or polyhaloalkyl. 64, the compound has the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 53, and Y_2 is independently Y_1 54. The method of claim 53, wherein R_5 is hydrogen, alkyl or halogen. 65. The compound has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1, X_2, X_3, R_1, Y_1 are as shown in claim 53, and Y_2 is independently R_6, R_
54. The method of claim 53, wherein 7 is independently hydrogen, alkyl or halogen. 66, Compounds of the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 represents halogen; X_2 and X_3 independently represent hydrogen or halogen;
Y_1 independently represents halogen, alkyl, alkoxy, nitro or cyano; m has a value of 0 to 2; R_1 is an acyclic or cyclic acetal group, an acyclic or cyclic dithioacetal group, an acyclic Formula or cyclic hemitioacetal group, aldehyde group, carboxylic acid group or its ester derivative, hydroxyalkyl group, alkoxyalkyl group,
represents an acyloxyalkyl group, an alkenyl group, or an alkylcarbonyl group, provided that when R_1 is a carboxylic acid group or its ester derivative, m has a value of 2, and R_1 is in the 2-position or Z is a substituted or unsubstituted, saturated or unsaturated monocyclic ring system; or (ii) a substituted or unsubstituted, saturated or unsaturated ring system; Bicyclic fused rings, wherein at least one ring is a 6-membered unsaturated carbocyclic ring and the second ring is a 5- or 6-membered carbocyclic ring or a carbonyl group or one or two rings. is a 5- or 6-membered heterocyclic ring that can contain oxygen or sulfur atoms in any combination, the method for producing acryloxy of the following formula: ▲ Numerical formula, chemical formula, table, etc. A method that involves reacting aniline with benzoyl isocyanate of the following formula: ▲Mathematical formula, chemical formula, table, etc.▼. 67. Compounds with the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 represents halogen; X_2 and X_3 independently represent hydrogen or halogen;
Y_1 independently represents halogen, alkyl, alkoxy, nitro or cyano; m has a value of 0 to 2; R_1 is an acyclic or cyclic acetal group, an acyclic or cyclic dithioacetal group, an acyclic Formula or cyclic hemitioacetal group, aldehyde group, carboxylic acid group or its ester derivative, hydroxyalkyl group, alkoxyalkyl group,
represents an acyloxyalkyl group, an alkenyl group, or an alkylcarbonyl group, provided that when R_1 is a carboxylic acid group or its ester derivative, m has a value of 2, and R_1 is in the 2-position or Z is a substituted or unsubstituted, saturated or unsaturated monocyclic ring system; or (ii) a substituted or unsubstituted, saturated or unsaturated ring system; Bicyclic fused rings, wherein at least one ring is a 6-membered unsaturated carbocyclic ring and the second ring is a 5- or 6-membered carbocyclic ring or a carbonyl group or one or two rings. is a 5- or 6-membered heterocyclic ring that can contain oxygen or sulfur atoms in any combination), an aryloxyphenylisocyanate of the following formula: A method that involves reacting with a benzamide of the following formula: ▲Mathematical formula, chemical formula, table, etc.▼. 68, Compounds of the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 represents halogen; X_2 and X_3 independently represent hydrogen or halogen;
Y_1 independently represents halogen, alkyl, alkoxy, nitro or cyano; m has a value of 0 to 2; R_1 is an acyclic or cyclic acetal group, an acyclic or cyclic dithioacetal group, an acyclic Formula or cyclic hemitioacetal group, aldehyde group, carboxylic acid group or its ester derivative, hydroxyalkyl group, alkoxyalkyl group,
represents an acyloxyalkyl group, an alkenyl group, or an alkylcarbonyl group, provided that when R_1 is a carboxylic acid group or its ester derivative, m has a value of 2, and R_1 is in the 2-position or Z is a substituted or unsubstituted, saturated or unsaturated monocyclic ring system; or (ii) a substituted or unsubstituted, saturated or unsaturated ring system; Bicyclic fused rings, wherein at least one ring is a 6-membered unsaturated carbocyclic ring and the second ring is a 5- or 6-membered carbocyclic ring or a carbonyl group or one or two rings. a 5- or 6-membered heterocyclic ring that can contain oxygen or sulfur atoms in any combination). A method that involves reacting substituted urea of the following formula: ▲Mathematical formula, chemical formula, table, etc.▼ with benzoyl chloride of the following formula: ▲Mathematical formula, chemical formula, table, etc.▼.