AU635839B2 - Pyrimidine derivatives - Google Patents

Description

)m

AUSTRALIA

PATENTS ACT 1952 Form COMPLETE SPECIFICATION

(ORIGINAL)

FOR OFFICE USE Short Title: Int. Cl: Application Numbe,: Lodged: Complete Specification-Lodged: Accepted: Lapsed: Published: Priority: Related Art: 635339 TO BE COMPLETED BY APPLICANT Name of Applicant: i.

Address of Applicant: SUMITOMO CHEMICAL COMPANY,

LIMITED

5-33, KITAHAMA-4-CHOME

CHUO-KU

OSAKA

JAPAN

GRIFFITH HACK CO., 601 St. Kilda Road, Melbourne, Victoria 3004, Australia.

Actual Inventor: Address for Service: Complete Specification for the invention entitled: PYRIMIDINE DERIVATIVES.

The following statement is a full description of this invention including the best method of performing it known to me:- 1 The present invention relates to a novel pyrimidine derivative, a method for producing the same, its use as a herbicide and an intermediate of the same.

European Patent Application No. 0223 406A1, 0249 708A1, 0249 707A1, etc. disclose that pyrimidine derivatives can be used as an active ingredient for herbicides.

However, these compounds are not always said to be satisfactory because they are insufficient in i0 herbicidal activity.

On the other hand, a large number of S. e herbicides for crop lands or non-crop lands are now in use. However, there are.many kinds of weeds to be controlled and generation of the weeds extends over a 0 15 long period of time, so that development of herbicides having a higher herbicidal activity and a broader herbicidal spectrum than before is being desired.

Further, in recent years, no-till cultivation has been carried out for the purposes of saving labor, extending S* 20 cultivation period, preventing soil erosion, etc.

Therefore, it is being much desired to develop herbicides having both a high post-emergence herbicidal activity against weeds and pre-emergence herbicidal activity, their excellent residual activity at high level, and a high selectivity to the undesired weeds as 1 compared with the desired crops when crops are cultivated after application of herbicides.

In view of the situation like this, the present inventors have extensively studied, and as a result, have found that pyrimidine derivatives represented by the following formula are compounds having an excellent herbicidal activity and having few foregoing defects, and that some of the derivatives have a high selectivity to the undesired weeds as compared with the desired crops. That is, the pyrimidine derivative can control the undesired weeds widely te generated in crop lands or non-crop lands at low dosage rates, has a broad herbicidal spectrum and also can safely be used for no-till cultivation. The present 15 invention is based on this finding.

According to the present invention, there are provided a pyrimidine derivative having the formula (hereinafter present compound), co Y3 z COA *1I S Y2 (1) R1 N -R 2 wherein A is C 3

-C

8 cycloalkyl CI-C 6 alkyl, C 3

-C

8 cycloalkyl C 1

-C

6 alkyl substituted with at least one member selected from the group consisting of CI-C 6 l, C lkoxy halo C-C alkyl -C alkoxyalkyl, Ci-C 6 alkoxy, halo CI-C 6 alkyl, C1-C 6 alkoxy- 1 carbonyl and halogen, C 3

-C

6 oxacycloalkyl, C 3

-C

6 oxacycloalkyl substituted with at least one member selected from the group consisting Of Cl-C 6 alkyl, Cl-C 6 alkoxy, halo C 1 -C6 alkyl, C 1

-C

6 alkoxycarbonyl and halogen, C 3

-C

6 oxacycloalkyl C 1

-C

6 alkyl, C 3

-C

6 oxacycloalky. Cl-Ce alkyl substituted with at least one member selected f rom the group consisting of Cl-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, C 3

-C

5 dioxacycloalkyl, C 3

-C

5 dioxacycloalkyl substituted with at least one member selected from the group consisting of Cl-C 6 alkyl, C 1

-C

6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, C 2

-C

5 dioxacycloalkyl Cl-Ce alkyl or C 2

-C

5 dioxacycloalkyl C 1

C

6 *..alkyl substituted with at least one member selected from the group consisting of Cl-C 6 alkyl, C 1

-C

6 alkoxy, halo Cl-C6 alkyl, CI-C6 alkoxycarbonyl and halogen; each of R1 and R 2 which may be the same or differnt, is Cl-C 6 alkyl, Cl-Ce alkoxy, halo C 1

-C

6 alkoxy or halogen; 20 X is oxygen or sulfur; Z is nitrogen or CY4; each of Yl, y2 and YL3, which may be the same :or different, is hydrogen, halogen, Cl-C6 alkyl or Cl-C6 alkoxy; and y4 is hydrogen, hydroxyl, mercapto, nitro, halogen, Cl-C6 alkyl, C 2

-C

6 alkenyl, C2-C6 alkynyl, Ci-C6 alkoxy, C 3

-C

6 alkenyloxy, C 3 -C6 alkynyloxy, halo Cl-C 6 alkyl, halo C 2 alkenyl, halo C2-C6 alkynyl, halo Cl-C 6 1alkoxy, halo C 3

-C

6 alkenyloxy, halo C 3

-C

6 alkynyloxy, Cl-C 6 alkoxy Cl-C 6 alkyl, C 3

-C

6 alkenyloxy C 1

-C

6 alkyl,

C

3

-C

6 alkynyloxy Cl-C 6 alkyl, cyano, formyl, carboxyl, Cl-C 6 alkoxycarbonyl, C 3

-C

6 alkenyloxycarbonyl, C 3

-C

6 alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of Cl-C 6 alkyl, C 1

-C

6 alkoxy, halo C 1

-C

6 alkyl, C 1

-C

6 alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected f rom the group consisting of Cl-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected f rom the group consisting of Cl-C!- alkyl, Cl-C 6 &Ikoxy, *halo C 1 alkyl, CI-C 6 alkoxycarbonyl and halogeft, 15 benzyloxi-', benzyloxy substituted with at least one member selected f rom the group consisting of Cl-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxy- A carbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group 20consstin ofCI-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, S

R

6 wherein each of R5 and R6, which may be the same or different, is hydrogent Cl-Cs alkyl, C 3

-C

6 alkenyl or

C

3

-C

6 alkynyl, 11 1wherein R5 and R6 are as defined above, -S -R 7

M

00 00 000 00 0 0 0000 see.

0 3400 0* 0 0 0e 0 000 wherein R7 is Cl-C 6 alkyl, C 3

-C

6 alkenyl or C 3

-C

6 alkynyl and m is an integer of 0, 1 or 2 0 -X1 -R wherein X1 is oxygen su-lfur, and R 7 is as defined above, or

CH

2 S R 7 11 (O)m wherein R 7 and m are as defined above, and n is an integer of from 1 to 4; a method for producing the pyrimidine derivative (1) which comprises reacting a compound having the formula, 0 006000 0 *00* 06 0* C 00 @0 0 000 6 @0 00 0s S 0 a £5000.

9

O

0 Y3 II z

COA

y T2 XH (2) y2 I

XH

yi 1 wherein A, X, Z, Y1, Y2 and Y3 are as defined above, with a compound having the formula, R1 N (3)

N

R2 0 Of14 wherein each of R 1 and R 2 are as defined above; W is halogen or S R8

II

(o)e 0 M wherein R8 is C1-C 6 alkyl, benzyl or benzyl substituted with at least one member selected from the group consisting of C1-C 6 alkyl, Cl-C 6 alkoxy, halogen or nitro; and e is an integer of 0, 1 or 2; a method for producing the pyrimidine derivative (1) which comprises the steps of reacting a carboxylic acid derivative having the formula 0 y3 II Z

COH

SR1 Y2 y (4) Y1 N S, 1 wherein X, Z, yl, y2, Y3, R1 and R 2 are as defined above, with an acid-halogenating agent or an active esterifying agent to obtain a reaction product; and (ii) reacting the reaction product with an alcohol 5 derivative having the formula, 0*

OS*

HO-A 64 wherein A is as defined above; a method for producing the pyrimidine derivative (1) which.comprises reacting a carboxylic acid derivative a* having the formula *4 -l 0 3 COH

R

1

N

2 yi N R2 wherein Xp Z, yl, Y2, Y3, R 1 and R 2 are as defined above, with a halide having the formula,

W

3 -A (7) 1 wherein A is as defined above, and W3 is halogen; a compound having the formula, 0 y3 II

COA

y2 XH (2) yl wherein A, X, Z, Y1, y2 and Y3 are as defined above; a herbicidal composition which comprises as an active 5 ingredient a herbicidally effective amount of the pyrimidine derivative described above, and an inert carrier or a diluent; a method for controlling undesirable weeds, which 0a..4.

comprises applying the above herbicidal composition to n a 10 an area where undesirable weeds grow or are likely to grow; and a use of the pyrimidine derivative as a herbicide.

In the formula examples of the C 1

-C

6 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tett-butyl, n-haxyl, etc; examples of the C 1

-C

6 alkoxy group inclure methoxy, ethoxy, npropoxy, isopropoxy, n-butoxy, hexyloxy, etc; and examples of the C 1 -Cs alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-butoxycarbonyl, hexyloxycarbonyl, etc.

1 The halogen atom in the formula includes fluorine, chlorine, bromine and iodine.

When a C 3

-C

6 oxacycloalkyl Cl-C 6 alkyl group is selected as A, the examples thereof include oxacyclobutylmethyl, oxacyclobutylethyl, oxacyclobutylpropyl, oxacyclobutylpentyl, oxacyclobutylhexy'i, oxacyclopentylmethyl, oxacyclopentylethyl, oxacyclopentylpropyl, oxacyclopentylpentyl, oxacyclopentylhexyl, oxacyclohexylmethyl, oxacyclohexylethyl, oxacyclohexylbutyl, oxacyclohexylpentyl, oxacyclohexylhexyl, oxacycloheptylmethyl, oxacycloheptylethyl, oxacycloheptylbutyl, oxacycloheptylpentyl, oxacycloheptylhexyl, methyloxacyclobutylmethyl, dimethyloxacyclobutylethyl, ethyloxacyclobutylpropyl, hexyloxacyclobutylbutyl, chioro- 15 oxacyclobutylpentyl, dichlorooxacyclobutylhexyl, difluorooxacyclopentylmethyl, broiuooxacyclopentylethyl, methoxyoxacyclopentylpropyi, ethoxyoxacyclopentylbutyl, hexyloxyoxacyclopentylpentyl, trifluoromethyloxacyclopentylhexyl, methoxycarbonyloxacyclohexylmethyl, ethoxycarbonyloxacyclohexylethyl, hexyloxycarbonyloxacyclohexylpropyl group, etc.

as AWhen a C 3

-C

5 dioxacycloalkyl group is selected aAthe examples the-reof include dioxacyclopentyl, dioxacyclohexyl, dioxacycloheptyl, inethyldioxacyclopentyl, dimethyldioxacyclohexy-, chlorodioxacycloheptyl group, etc.

When a C 3

-C

5 dioxacycloalkyl Cl-C 6 alkyl group is selected as A, the examples thereof include dioxa- /0 1cyclopentylmethyl, dioxacyclopentylethyl, dioxacyclopentylbutyl, dioxacyclopentylpentyl, dioxacyclopentylhexyl, dioxacyclohexylmethyl, dioxacyclohexylethyl, dioxacyclohexylpropyl, dioxacyclohexylpentyl, dioxacyclohexyihexyl, dioxacycloheptylmethyl, dioxacycloheptylethyl, dioxacycloheptyipropyl, dioxacycloheptylpentyl, dioxacycloheptyihexyl group, methyldioxacyclopentylmethyl, dimethyldioxacyclohexylmethyl, ethyldioxacycloheptylmethyl, hexyldioxacyclopentylethyl, chiorodioxacyclohexylethyl, dichiorodioxacycloheptylethyl, difluorodioxacyclopentylproiyl, bromodioxacyclo- *::*hexyipropyl, methoxydioxacycloheptyipropyl, ethoxy- 0 dioxacyc'Lcpentylbutyl, hexyloxydioxacycichexylbutyl, :04"'0trifluoromethyldioxacycloheptylbutyl, methoxycarbonylded 15 dioxacycloPentylpentyl, ethoxycarbonyldioxacyclohexylpentyl, hexyloxycarbonyldioxacycloheptylpentyl group, etc.

*When a C 3

-C

8 cycloalkyl Cl-C 6 alkyl group is *do *selected as A, the examples thereof include cyclopropyl- 20 methyl, cyclopropylethyl, cyclopropylpropyl, cyclopropylpentyl, cyclopropylhexyl, cyclobutylmethyl, :o'4 00cyclobutylethyl, cyclobutyipropyl, cyclobutylpentyl, cyclobutyihexyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylbutyl, cyclopentylpentyl, cyclopentylhexyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylbut;l, cyclohexylpentyl, cyclohexylhexyl, cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl, cycloheptylpentyl, cycloheptylhexyl, cyclooctylmethyl, cyclooctylethyl, 1 cyclooctylbutyl, cyclooctylpentyl, cyclooctylhexyl, methylcyclopropylmethyl, dimethylcyclopropylethyl, ethylcyclopropyipropyl, hexylcyclopropylbutyl, chiorocyclopropylpentyl, dichiorocyclopropyihexyl, difluorocyclobutylmethyl, broiuocyclobutylethyl, methoxycyclobutyipropyl, ethoxycyclobutylbutyl, hexyloxycyclobutylpentyl, trifluoromethylcyclobutyihexyl group, methoxycarbonylcyclohexylmethyl, etoxycarbonylcyclohexylethyl, hexyloxycarbonylcyclohexyipropyl group, etc.

When a C 3

-C

6 oxacycloalkyl group is selected as A, the examples thereof include oxacyclobutyl, oxacyclopentyl, oxacyclohexyl, oxacycioheptylf methyloxacyclobutyl group, dime thyloxacyclopentyl, dichlorooxacyclohexyl, methoxyoxacycloheptyl group, etc.

15 When a halo Cl-C 6 alkoxy group is selected as R1 or R2, the examples thereof include fluoromethoxy, difluoromethoxy, trifluorornethoxy, etc.

*When a C 2

-C

6 alkenyl group is selected as Y4, the examples thereof include vinyl, allyl, 1-butenyl, 2butenyl, 3-butenyl, 2-pentenyl, 2-hexenyl, etc.

When a C 2

-C

6 alkynyl group is selected as Y4, the examples thereof include ethynyl, propargyl, 1butynyl, 2-butynyl, 2-pentynyl, 3-pentynyl, 2-hexynyl, etc.

When a C 3

-C

6 alkenyloxy group is selected as y4, the examples thereof include allyloxy, 2-butenyloxy, 3-butenyloxy,, 2-hexenyloxy, etc.

1 When a C 3

-C

6 alkynyloxy group is selected as y4, the examples thereof include propargyloxy, 2butynyloxy, 3-butynyloxy, 2-hexynyloxy, etc.

When a halo Cl-C 6 alkyl group is selected as y4, the examples thereof include fluoromethyl, difluoromethyl, trifluoromethyl, 2-chioroethyl, 3bromopropyl, etc.

When a halo C 2

-C

6 alkenyl group is selected as y4, the examples thereof include 1-chiorovinyl, 3chloroallyl, 5-bromo-2-pentenyl, 6-iodo-2-hexenyl, 5-trifluoro-2-pentenyl, etc.

When a halo C 2

-C

6 alkynyl group is selected as 'Y4, the examples thereof include 2-iodoethynyl, 2-pentynyl, 6--iode-2-hexynyl, 5,5,5-trifluoro-2- 15 pentynyl, etc.

When a halo Cj-C 6 alkoxy group is selected as Y4, the examples thereof include fluoromethoxy, difluoromethoxy, trifluoroniethoxy, 1,1,2, 2-tetrafluoroethoxy, etc.

20 When a halo 6 3

-C

6 alkenyloxy group is selected as y4, the examples thereof include 3-chloroallloxYr bromo-2-pentenyloxy, 6-iodo-2-hexenyloxy, 5,5,5- 94*4:trifluoro-2-pentenyloxy, etc.

When a halo C 3

-C

6 alkynyloxy group is selected as y4, the examples thereof include 5-bromo-2-pentynyloxy, 5-chloro-2-pentynyloxy, 3-iodopropargyloxy, etc.

When a Cl-C 6 alkoxy Cl-C6 alkyl group is selected as y4, the examples thereof include methoxy- I methyl, ethoxymethyl, 2-methoxyethyl, 4-n-propoxybutyl, 2-n-butoxyethyl, 6-hexyloxyhexyl, etc.

When a C 3

-C

6 alkenyloxy Cl-C 6 alkyl group is selected as y4, the examples thereof include allyloxymethyl, 2-allyloxyethyl, 4-allyloxybutyl, 3-(2butenyloxy)propyl, 6-(hexenyloxy)hexyl, etc.

When a C 3

-C

6 alkynyloxy C 1

-C

6 alkyl group is selectd as Y4, the examples thereof include propargyloxymethyl, 2-propargyloxyethyl, 4-propargyloxybutyl, 3- (2-butynyloxy)propyl, 6-(2-hexynyloxy)hexyl, etc.

When a C 3

-C

6 alkenyloxycarbonyl group is p. selected as y4, the examples thereof include allyloxycarbonyl, 2-butenyloxycarbonyl, 3-butenyloxycarbonyl, 2hexenyloxycarbonyl, etc.

15 When a C 3

-C

6 alkynyloxycarbonyl group is selected as y4, the examples thereof include propargyloxycarbonyl, 2-butynyloxycarbonyl, 3-butynyloxycarbonyl, 2-hexynyloxycarbonyl, etc.

When a substituted phenoxy group is selectd as y4, the examples thereof include 2-methylphenoxy, 3ethyiphenoxy, 4-hexylphenoxy, 2, 6-dimethylphenixy, 3methoxyphenoxy, 4-isopropoxyphenoxy, 3-hexyloxyphenoxy, 2-trifluoromethylphenoxy, 3-difluoromethyiphenoxy, 2methoxycarbonylphenoxy, 2-ethoxycarbonylphenoxy, 2-npropoxycarbonylphenoxy, 2-hexyloxycarbonylphenoxy, 2fluorophenoxy, 2-chlorophenoxy, 3-bromophenoxy, 2,4dichiorophenoxy, etc.

1 When a substituted phenyl group is selected as y4, the examples thereof include 2-methyiphenyl, 3ethyiphenyl, 4-hexylphenyl, 2,6-dimethyiphenyl, 3methoxyphenyl, 4-isopropoxyphenyl, 3-hexyloxyphenyl, 2trifluoromethyiphenyl, 3-difluoromethyiphenyl, 2methoxycarbonyiphenyl,[ 2-ethoxycarbonyiphenyl, 2-npropoxycarbonyiphenyl, 2-hexyloxycarbonylphenyl, 2fluorophenyl, 2-chloirophenyl, 3-bromophenyl, 2,4dichiorophenyl, etc.

When a substituted phenylthio group is selected as y4, the examples thereof include 2-methylphenylthio, 3-ethylphenylthio, 4-hexylphenylthio, 2,6dimethylphenylthio,- 3-methoxyphenylthio, 4-isopropoxyphenylthio, 3-hexyloxyphenylthio, 2-trifluoromzthyl- 15 phenylthio, 31-difluoromethylphenylthio, 2-methoxycarbonylphenylthio, 2-ethoxycarbonylphenylthio, 2-nprcpoxycarbonylphenylthio, 2-hexyloxycarbonylphenylthio, 2-fluorophenylthio, 2-chlorophenylthio, 3-bromophenylthio, 2, 4-dichlorophenylthio, etc.

When a substituted benzyloxy group is selectd as y4, the examples thereof include 2-methylbenzyloxy, 3-ethylbenzyloxy, 4-hexylbenzyloxy, 2, 6-dimethylbenzyl- 3-methoxybenzyloxy, 4-isopropoxybenzyloxy, 3hexyloxybenzyloxy, 2-trifluoromethylbenzyloxy, 3difluoromethylbenzyloxy, 2-methoxycarbonylbenzyloxy, 2ethoxycarbonylbenzyloxyr 2-n-propoxycarbonylbenzyloxy, 2-h xyloxycarbonylbenzyloxy 2-fluorobenzy,oxy, 2chlorobenzyloxy, 3-bromobenzyloxy, 2, 4-dichiorobenzyloxy, etc.

When a substituted benzylthio group is selected as y4 the examples thereof include 2-methylbenzylthio, 3-ethylbenzylthio, 4-hexylbenzylthio, 2,6dimethylbenzylthio, 3-methoxybenzylthio, 4-isopropoxybenzylthio, 3-hexyloxybenzylthio, 2-trifluoromethylbenzyl'thio, 3-difluoromethylbenzylthio, 2-methoxycarbonylbenzylthio, 2-ethoxycarbonylbenzylthio, 2-npropoxycarbonylbenzylthio, 2-hexyloxycarbonylbenzylthio, 2-flJuorobenzylthio, 2-chlorobenzylthio, 3-bromobenzylthio, 2, 4-dichlorobenzylthio, etc.

0:00 When a C 3

-C

6 alkenyl group is selected as R 5 R6 or R 7 ,*the examples thereof include allyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 2-hexenyl, etc.

When a C 3

-C

6 alkynyl group is selected as R 5 R6 or R 7 the examples thereof include propargyl, 1- 0 0 butynyl, 2-butynyl, 2-pentynyl, 3-pentynyl, 2-hexynyl, etc.

20 In the compound of the formula the substituents R1 and R 2 which may be the same or V~toodifferent, are preferably CI-C 6 alkoxy, and more preferably, both of them are methoxy.

A is pref erably a C 3

-C

5 dioxacycloalkyl Cl-C 6 alkyl group. More preferably, A is l,3-dioxolane-2-yl

C

1

-C

6 alkyl group or l,,3-dioxan-2-yl Cl-C 6 alkyl group.

Most preferably, A is l 13-dioxolane-2-yl ethyl group or l,3-dioxan-2-yl ethyl group.

16 1 X is preferably oxygen.

5 5 Z is preferably nitrogen or CY wherein Y is hydrogen or halogen, a halo C1-C6 alkyl group, a C -C6 alkyl group, a C 1

-C

6 alkoxy group or a substituted or unsubstituted phenyl group. More preferably, Z is nitrogen or CY 5 in which Y is hydrogen or halogen. Most preferably, Z is CY 5 and Y5 is halogen.

Y and Y 2 which may be the same or different, are preferably a hydrogen atom or a fluorine atom.

3 0 y is preferably hydrogen, fluorine or a C1-C 6 alkoxy group. Specific examples of the pyrimidine derivative of the peresent invention include 2-(1,3dioxan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl) S. oxybenzoate,

C-O

N O OMe SOMe 2-(1,3-dioxan-2-yl)ethyl 2-chloro-6-(4,6-dimethoxypyrididin-2-yl)oxybenzoate, 4

O

-O O N OMe o Va N OMe and 12-(l,3-dioxa. -2-yl)ethyl 3-(4,6-dimethoxypyrimidin-2yl) oxypi.,;olinate, N 0 N 014e OMe A method for producing the present compound is as follows.

5 The present compound can be produced by reacting a compound represented by the formula v 3 z -A y2 xii (2) ~**wherein"A, X, yl, y2, y3 and Z are as defined above, with 1 a compound represented by the formula AN-74 (3) N R2 *Bwherein RI, R 2 and W aieo as defined above.

reaction is usually carried out with or without a solvent in the presence of a base. The readtion temperature upunally ranges from room temperature to the boiling point of the solvent, and the reaction time usually ranges from 10 minutes to 24 1 hours. Referring to the amounts of the reagents used for this reaction, the amount of the compound is ,usually 1.0 to 1.5 equivalents based on 1 equivalent of the compound and that of the base is usually 1.0 to 5.0 equivalents based on the same. The solvent includes aliphatic hydrocarbons hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons benzene, toluene, xylene), halogenated hydrocarbons (e.g.

chloroform, carbon tetrachloride, dichloroethane, chlotobenzene, dichlorobenzene), ethers diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), ketones (e.g.

acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), alcohols methanol, 15 ethanol, isopropanol, tert-butanol, octanol, cyclohexanol, methyl cellosolve, diethylene glycol, glycerin), esters ethyl formate, ethyl acetate, butyl acetate), nitro compounds nitroethane, nitrobenzene), nitriles acetonitrile, S 20 isobutyronitrile), tertiary amines pyridine, triethylamine, N,N-diethylaniline, tributylamine, Nmethylmorpholine), acid amides formamide, N,Ndimethylformamide, acetamide), sulfur compounds (e.g.

dimethyl sulfoxide, sulfolane), liquid ammonia, water and the mixtures thereof.

Specific examples of the base are organic bases pyridine, triethylamine, N,N-diethylaniline), inorganic'bases sodium hydroxide, 1 potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride), alkali metal alkoxides (e.g.

sodium methoxide, sodium ethoxide), etc.

After completion of the reaction, the reaction solution may be after-treated as usual. That is, water is added to the solution which is then extracted with an organic solvent and concentrated, and if necessary, the product obtained is subjected to chromatography, distillation, recrystallization, etc. Thus, the desired present compound can be obtained.

The compound represented by the formula (3) can be produced according to Japanese Patent Application Kokai No. 63-23870, J. Org. Chem., 26, 792 (1961), etc.

The present compound can also be produced by 15 reacting a compound represented by the formula 0 Y3 Z COH Yy2 (4) yl N N -R2 OS wherein R1, R 2 X, Yl, Y2, y3 and Z are as defined above, 9 with an acid-halogenating agent or an active esterifying agent (hereinafter reaction and reacting the resulting reaction product with an alcohol derivative represented by the formula

HO-A

S.

5

**SS

*5 S

S

*es

S

*5S* S S S. p S S *SS S *5 5 p 0 .55590 1 wherein A is as defined above thereina~fter reaction (ii).

In the above reaction specif .1 %mples of the acid-halogenating agent are thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachioride, phosphorus oxychlo".eide, phosgene, oxalic acid elichioride, etc.

Specific examples of the active esterifying agent are N,NI-disubstituted carbodiimides such as N,N'dicyclohexY-lcarbodiimide, NrN' -diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropy-L) carbodiimide hydrochloride, etc.; arylsulfonyl chlorides such as 2,4,6-trimethylbenzenesulfonyl chloride, 2,4,6triisopropylbenzenesulfonlyl chloride, etc.; N,N'- 15 carbonyldiimidazole; diphenylphosphorylazide; Nethoxycarbonyl-2-ethoxy-l, 2-dihydroquinoline; N-ethyl- 2 '-hydroxybenzisoxazolium trifluoroborate; phenylisoxazolium-3 '-sulfonate; etc.

By this reaction, a compound represented by 20 the formula '11' y3 z C-W2 y2 Y1 N R N

R

1 wherein R1, R 2 X, Y1, Y2, y3 and Z are as defined above, is produced in the reaction system.

In the above formula a substituent W2 represents a halogen atom when the acid-halogenating agent was used; W2 represents an N,N'-disubstituted-2isoureido group when N,N'-disubstituted carbodiimide was used as the active esterifying agent; W 2 represents an arylsulfonyloxy group when arylsulfonyl chloride was used as said agent; W2 represents an imidazolyl group when N,N'-carbonyldiimidazole was used as said agent; W 2 represents an azide group when diphenylphosphorylazide was used as said agent; W2 represents an ethoxycarbonyloxy group when N-ethoxycarbonyl-2-ethoxy-1,2- 9.

dihydroquinoline was used as said agent; W2 represents a 15 3-(N-ethylaminocarbonyl)-2-hydroxyphenoxy group when Nethyl-2 -hydroxybenzisoxazolium trifluoroborate was used as said agent; and W2 represents a group

SO

3 e see** S03 e I O- when H CONHC 2

HS

3'-sulfonate was used as said agent.

20 In the reacton system, W2 can also take a form of acid anhydride containing the moiety represented by the formula,

O

Y3 z CO- Y2 'R R1 N R2 1 wherein RI, R 2 X, yl, Y2, Y3 and Z are as defined above.

The amount of the foregoing acid-halogenating agent or active esterifying agent used is usually 1 to 10 equivalents based on 1 equivalent of the compound 5 represented by the formula The amount of the alcohol derivative of the formula used is usually 1 to 5 equivalents based on 1 equivalent of the compound represented by the formula 10 The reactions and (ii) can also be carried 9 out, if necessary, in the presence of a base. Such a base includes organic bases 1-methylimidazole, 3nitro-lH-1,2,4-triazote, 1H-tetrazole, 1H-1,2,4triazole, imidazole, pyridine, triethylamine) and inorganic bases potassium carbonate). The amount **ass$ of the base used is usually 1 to 20 equivalents based on 1 equivalent of the compound represented by the formula The reactions and (ii) are usually carried out in the presence of an inert solvent. Such a solvent includes aliphatic hydrocarbons hexane, heptane, 1 ligroin, petroleum ether), aromatic hydrocarbons (e.g.

benzene, toluene, xylene), halogenated hydrocarbons chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), ketones (e.g.

acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), esters ethyl formate, ethyl acetate, butyl acetate), nitro compounds (e.g.

nitroethane, nitrobenzene), nitriles acetonitrile, isobutyronitrile), tertiary amines pyridine, S" triethylarfine, N,N-diethylaniline, tributylamine, Nmethylmoipholine), acid amides N,N-dimethylformamide), sulfur compounds dimethyl sulfoxide, 15 sulfolane) and the mixtures thereof.

Generally, the reaction temperature usually ranges from 0°C to the boiling point of the solvent in a any of the reactions and The reactio. time d* usually ranges from 1 to 24 hours for each reaction, and 20 from about 1 to about 48 hours through the reactions (i) and (ii).

After completion of the reaction, the reaction solution may be after-treated as usual. That is, water is added to the solution which is then extracted with an organic solvent and concentrated, and if necessary, the product obtained is subjected to the chromatography, distillation, recrystallization, etc. Thus, the desired present compound can be obtained.

1 The present compound can also be prepard by reacting a compound represented by the formula with a halide represented by the formula (7)

W

3 -A (7) wherein A and W3 are as defi d above.

This reaction is usually carried out with or without a solvent in the presence of a base. The reaction temperature usually ranges from room temperature to the boiling point of the solvent, and the reaction time usually ranges from 30 minutes to 24 10 hours. Referring to the amounts of the reagents used for this reaction, the amount of the halide is usually 1.0 to 5.0 equivalents based on 1 equivalent of the compound and that of the base is usually 1.0 to equivalents based on the same. Examples of the solvent 15 include aliphatic hydrocarbons hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g.

benzene, toluene, xylene), halogenated hydrocarbons chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers diethyl b 20 ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether) and ketones (e.g.

acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), esters ethyl formate, ethyl acetate, butyl acetate), nitro compounds (e.g.

nitroethaa, nitrobenzene), nitriles acetonitrile, 1 isobutyronitrile), tertiary amines pyridine, triethylamine, N,N-diethylaniline, tributylamine, Nmethylmorpholine), acid amides formamide, N,Ndimethylformamide, acetamide), sulfur compounds (e.g.

dimethyl sulfoxide, sulfolane), and mixtures thereof.

The base includes organic bases (e.g.

pyridine, triethylamine, N,N-diethylaniline), inorganic bases sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride), alkali metal alkoxides sodium methoxide, sodium ethoxide), etc.

After completion of the reaction, the reaction solution is after-treated as usual. That is, water is added to the solution which is then extracted with an 15 organic solvent and concentrated, and if necessary, the product obtained is subjected to chromatography, distillation, recrystallization, etc. Thus, the desired present compound can be obtained.

The compound represented by the formula (4) 20 can be produced according to EP 0 223 406 Al, etc.

In producing the present compounds, when the compound (a starting material for compound represented by the formula is other than the

H

compounds in which Y4 is a group, -N R R6 in which R6 0

S

H

is as defined above, or a group, -C-N

R

in which R6 1 is as defined above, said compound can be produced as follows: The method comprises reacting an aromatic carboxylic acid halide represented by the following formula 0 11 Y3 C-W4 0 y2 X X-C-R 9 (8 5 wherein X, Yl, y2 and y3 are as defined above, W4 .:..represents a halogen atom, R 9 represents a Cl-Cs alkyl see: group, and ZI represents Cy4' wherein y4' is hydrogen, -nitro, halogen, Cl-C 6 alkyl, C 2

-C

6 alkenyl, C 2

-C

6 alkynyl, Cj-(426 alkoxy, C 3

-C

6 alkenyloxy, C 3

-C

6 alkynyloxy, halo CI-C 6 alkyl, halo C 2

-C

6 alkenyl, halo C%2-C6 alkynyl, halo Cj,-C6 alkoxy, halo C 3

-C

6 alkenyloxy, *.**halo C 3

-C

6 alkynyloxy, Ca-C6 alkoxy tQI-C 6 alkyl, C 3

-C

6 alknylxyCl-C 6 alkyl, C 3 -C6 alkynyloxy Ca-C6 alkyl, cyanrt~ formyl, carboxyl, Cl-Cs alkoxycarbonyl, C3-C6 alkenyloxycarbonyl, C 3

-C

6 alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected 4:64%from the group consisting Of Cl-Cs alkyl, Cl-Cs alkoxy, halo Cl-Cs alkyl, Cl-Cs alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected ;front the group consisting of Cl-C 6 alkyl, Ca-Cs alkoxy, halo Cl-C 6 alkyl, Cl-C6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at 27 1 least one member selected from the group consisting of Cj.-C6 alkyl, Cj-C 6 alkoxy, halo Cj-C6 alkyl, CI-C6 alkoxycarbonyl and haiogen, bernzyloxy, benzyloxy substituted with at least one member selected from the group consisting of Cj-C 6 alkyl, Cl-C 6 alkoxy, halo CI-C 6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group consisting Of Cl-Cs alkyl, Cl-Cs alkoxy, halo C 1

-C

6 alkyl, Cl-C6 alkoxycarbonyl and halogen, ~R51 10 wherein each'of R5' and RV 1 which may be the same or different, is Cj-C 6 alkyl, C 3 -C6 alkenyl Or C 3 -C6 alkynyl, 0 wherein Rs' and RV5 are as defined above, S R7 wherein R7 and m are as defined above, 0 .X -C -R7 -28 1 wherein R7 and XI are as defined above, or CHGi 2 niu S R 11 (O)m wh,!';rein R7, m and n are as defined above, or a group represented by the formula, -X .CR in which R 9 and

S

0e0 0a S S 0~00 *S .0 405o 00 0 0

SOS'

00 00 000

S

055050 0 05 00 0 06 S 0 000 Xare as defined above, with the alcoholderivative represented by the formula in the presence of a dehydrohalogenating agent and hydrolyzing the resulting compound with a base sodium hydroxide, potassium hydroxide) or an acid hydrochloric acid, sulfuric 0 acid) to re7move the group, -C-R 9 .0 Or alternatively, the method comprises reacting a compound represented by the formula,

C-OH

0 1 XCR9 sea$%.

a 0 wherein X, yJ., y2, y3, ZI and R 9 are as defined above, 'with the compound 1 in the presence of a dehydrohalogenating agent and hydrolyzing the resulting compound with a base sodium hydroxide, potassium hydroxide) or an acid (e.g.

hydrochloric acid, .alfuric acid) to remove the group, 0

II

-C-R

9 Specific examples of the dehydrohalogenating agent are pyridine, triethylamine, NN-diethylaniline, etc.

After completion of the reaction, the reaction S* 10 solution may be after-treated as usual. That is, water is added to the solution which is then extracted with an S organic solvent and concentrated, and if necessary, the product obtained is subjected to the chromatography, distillation, recrystallization, etc. Thus, the compound can be obtained.

The compound represented by the formula (2) can be produced by reacting an aromatic carboxylic acid derivative represented by the formula

O

Y3 z .COH y2 XH (9) Y1 wherein X, yl, Y2, y3 and Z are as defined above, with an acid-halogenating agent or an active esterifying 30 1 agent (hereinafter reaction (iii), and reacting the resulting reaction product with the alcohol derivative represented by the formula (hereinafter reaction The above reactions (iii) and (iv) can be carried out according to the foregoing reactions and respectively. The aromatic carboxylic acid halide derivative can be produced according to Beilstein H10/p.86, EI10/p.42 0/p.55, EIIIl0/p.151, EIV10/p.169, etc.

The aromatic carboxylic acid derivative (9) can be produced according to J. Org. C'bn., 27, 3551 (1962), Chem. Pharm. Bull., 31, 407 (1983), Yakugaku Zasshi, 99, 657 (1979), Chem. Pharm. Bull., 27, 1468 15 (1979), J. Med. Chem., 21, 1093 (1978), Yakugaku Zasshi, 92, 1386 (1972), Eur. J. Med. Chem-Chim. Ther., 21, 379 (1986), J. Chem. Scc., Perkin Trans. 1, 2069 (1979), J.

Chem. Soc., Perkin Trans. 1, 2079 (1979), J. Chem. Soc., Chem. Commun., 1127 (1968), J. Med. Chem., 31, 1039 20 (1988), Indian J. Chem., 25B, 796 (1986), J. Am. Chem.

Soc., .107, 4593 (1985), J. Org. Chem., 50, 718 (1985), J. Agric. Food Chem., 32, 747 (1984), J. Pharm.

Pharmacol., 35, 718 (1983), J. Org. Chem., 48, 1935 (1983), J. Chem. Soc., Chem. Commun., 1974, 362, etc.

Compound includes its stereo isomers having a'herbicidal activity. Compound includes its stereo isomers.

The present compounds have an excellent herbicidal activity and some of them have an excellent i 1 selectivity to the undesired weeds as compared with the desired crops.

That is, the present compound, when used for foliar treatment and soil treatment in upland fields, exhibits a herbicidal activity against a wide variety of undesired weeds. Also, the present compound when used for flooding treatment in paddy fields, exhibits a herbicidal activity against a wide variety of undesired weeds.

The present compound can control a wide range of weeds generated in crop lands or non-crop lands, can be applied in low dosage rates, has a broad 1* herbicidal spectrum and also can safely be used for notill cultivation in soybean fields, peanut fields, corn 15 fields; etc.

As weeds which can be controlled by the present comoound, there are mentioned for example broadleaved weeds s ch as wild buckwheat (Polygonum 4 convolvulus), pale smartweed (Polygonum lapathifolium), .s 20 common purslane (Portulaca oleracea), chickweed (Stellaria media), common lambsquarters (Chenopodium album), redroot pigweed (Amaranthus retroflexus), radish (Raphanus sativus), wild mustard (Sinapis arvensis), shepherds purse (Capsella bursa-pastoris), hemp sesbania (sesbania exaltata), sicklepod (Cassia obtusifolia), velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa), field pansy (Viola arvensis), cleavers (Galium aparine), ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea Pur'purea) field bindweed (Convolvulus ar'~ensis) red deadnettle (Lamium purpureum), henbit (Lamium, amplexicaure), jimsonweed (Datura stramonium), black nightshade (Solanum nigrum), birdseye speedwell. (Veronica persica), cocklebur (Xanthium strumarium), sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata), corn marigold (Chrysanthemum segetum) etcjl; Gramineae weeds such as Japanese millet (Echinochloa frumentacea), barnyardgrass (Echinochloa crus-galli), green foxtalJ.

(Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanciuinalis), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), oat (Avena sat va), wild oat (Avena fatua), johnsongrass (Sorghum ea 15 halepense), quackgrass (Agropyvron, repens), downy brome (Bromus tectorum), bermudagrass (Cynodon dactylon), etc.; Commelinaceae weeds such as dayflower (Commelina communis), etc.; and Cyperaceae weeds such as rice 4 0 flatsedge (Cyperus, iria), purple nutsedge (Cyperus rotundus), etc. In addition, the present compounds give such no phytotoxicity as becoming a problem to main crops such as corn, wheat, barley, rice, soybean, cotton, beet, etc.

In flooding treatment in paddy fields, the present compoundLs e);,'ibit a herbicidal activity against gramineous weeds such as barnyardgrass (Echinochloa oryzicola), etc.; broad-=leaved weeds such as false pimpernel (Lindernia procumbens), indian toothcup 1 (Rotala indica), waterwort (Elatine triandra), Ammannia multiflora, etc.; Cyperaceae weeds such as smallflower umbrellaplant (Cyperus difformis), bulrush (Scirpus juncoides), slender spikerush (Eleocharis acicularis), water nutgrass (gyperus serotinus), etc.; monochoria (Monochoria vaginalis), arrowhead (Saqittaria pygmaea), etc.

When the present compound is used as an active ingredient for herbicides, it is usually formulated before use into emulsifiable concentrates, wettable powders, suspension formulations, granules, water-dispersible granules, etc. by mixing the present compound with solid carriers, liquid carriers, *0 t surface active agents or other auxiliaries for 15 formulation.

The content of the compound as an active ingredient in these preparations is normally within a range of about 0.001 to 90% by weight, preferably of 0* about 0.003 to 80% by weight.

20 Ecxamples of the solid carriers are fine powders or granules of kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc, diatomaceous earth, calcite, walnut shell powders, urea, ammonium sulfate and synthetic hydrated silicon dioxide, etc.

Examples of the liquid carriers are aromatic hydrocarbons xylene, methylnaphthalene), alcohols isopropanol, ethylene glycol, cellosolve), ketones acetone, cyclohexanone, isophorone), vegetable 1 oils (soybean oil, cotton seed oil), dimethyl sulfoxide, N,N-dimethylformamide, acetonitrile, water, etc.

Examples of the surface active agents used for emulsification, dispersion or spreading, etc. are anionic surface active agents such as salts of alkyl sulfates, alkylsulfonates, alkylarylsulfonates, dialkyl sulfosuccinates, salts of polyoxyethylene alkylaryl ether phosphoric acid esters, etc., and nonionic surface active agents such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbit'n fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc.

Examples of the other auxiliaries for formulation are lignosulfonates, alginates, polyvinyl 15 alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl icid phosphate), etc.

The present compound is usually formulated into an appropriate formulation and used in soil Streatment, foliar treatment or flooding treatment before S. 20 e or after emergence of weeds. The soil treatment includes soil surface treatment and soil incorporation treatment. The foliar treatment includes, in addition 0 to the treatments of plants mentioned above, direct treatment in which the formulation is applied only to weeds so as to prevent the formulation from adhering to crops.

The herbicidal activity of the present compound can be expected to be increased by using 1 the compound in mixture with other herbicides. Further, the present compound can also be used in mixture with insecticides, acaricides, nematocides, fungicides, plant growth regulators, fertilizers, soil improvers, etc.

The present compound can be used as an active ingredient for herbicides used ir paddy fields, ridges of paddy fields, plowed fields, fields other than plowed fields, orchards, pastures, turfs, forests and fields other than agricultural fields, etc.

When the present compound is used as an active ingredient for herbicides, the dosage rate varies depending upon the weather conditions, preparation forms, when, how and where the treatment is carried out, 15 weeds species to be controlled, crops species to be protected, etc. Usually, however, the dosage rate is from 0.003 grams to 100 grams of the active ingredient per are, preferably from 0.01 grams to 50 grams of the active ingredient per are.

20 The herbicidal composition of the invention formulated in the form of an emulsifiable concentrate, a wettable powder or a suspension formulations may ordinarily be employed after diluting it with wat-t at a volume of about 1 to 10 liters per are. If necessary, auxiliaries such as a spreading agent are added to the water. The granules are usually applied as they are without being diluted.

1 Examples of the spreading agent are, in addition to the foregoin, surface active agents, substances such as polyoxyethylene resin acids (esters), lignosulfonates, abietates, dinaphthylmethanedisulfonates, paraffin, etc.

The present invention will be illustrated in more detail with reference to the following production examples, formulation examples and test examples, which are not however to be interpreted as limiting the invention thereto.

First, production examples for the present S. compound are shown.

a *9 Production Example 1 *9* 0.84 Gram of 2-(l,3-dioxan-2-yl)ethyl salicylate and 0.73 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was dissolved in 10 ml of N,N-dimethylformamide, and 0.51 g of anhydrous potassium carbonate was added thereto. The resulting solution was stirred at 1000 to 1100C for 1 hour. The reaction solution was 0 allowed to cool, poured into diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer separated from the aqueous layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue obtained was subjected to silica gel column chromatography (mfd. by Merck CO., Inc., solvent; chloroform) to obtain 0.50 g 1 of 2-(1,3-dioxan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2yl)oxybenzoate [preseiL compound 3H-NMR (CDC13) 6: 1.28-2.23 4H) 3.61-4.45 7H) 3.75 6H) 5.71 1H) 7.07-8.04 4H) Production Example 2 Milliliters of N,N-dimethylformamide in 10 which 0.22 g of 60% sodium hydride in oil has been 4 sus)pended was mixed with 5 ml of N,N-dimethylformamide solution of 1.38 g of 2-(4,6-dimethoxypyrimidin-2-yl)oxy benzoic acid. After stirring the mixture at room temperature for 30 minutes, 10 ml of N,N-dimethylformamide solution of 1.81 g of 2-(2-bromoethyl)-l,3dioxolane was added thereto. The resulting solution was stirred at 1000 to 110 0 C for 2 hours. The reaction solution was allowed to cool, poured into diluted hydrochloric acid, and extracted with ethyl acetate.

The organic layer separated from the aqueous layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue obtained was subjected to silica gel column chromatography (mfd.

by Merck Co., Inc., solvent: chloroform) to obtain 1.20 g of 2-(l,3-dioolan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate [present compound 1 1H-NMR (CDC1 3 6: 1.71-2.31 2H) 3.68-3.93 4H) 3.73 6H) 4.21 2H, J=6.4Hz) 4.79 1H, 5.67 1H) 7.08-7.98 4H) Production Example 3 0.55 Gram of 2-(4,6-dimethoxypyrimidin-2- S 10 yl)oxybenzoic acid, 0.21 g of tetrahydrofurfuryl alcohol and 0.85 g of 2,4,6-triisopropylbenzenesulfonyl chloride were dissolved in 5 ml of tetrahydrofuran. Subsequently, 0.45 g of 1-methylimidazole was added to the mixture. After stirring the resulting solution at room Poe Iemperature for 1 hour in order to carry out the reaction, the reaction solution was poured into diluted 1 hydrochloric acid, and exracted with ethyl acetate. The organic layer separated from the aqueous layer was washed with saturated sodium chloride solution and dried over anhydrrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue obtained 4 was subjected to silica gel column chromatography (mfd.

by Merck Co., Inc., solvent: chloroform) to obtain 0.30 g of tetrahydrofurfuryl 2-(4,6-dimethoxypyrimidin- 2-yl)oxybenzoate [present compound (III-9)].

1 111-NMR (CDCl 3 6: 1.45-2.15 (in, 4H1) 3.65-4.20 (mn, 511) 3.76 6H1) 5.73 111) 7.12-8.10 (in, 4H1) Productioni Example 4 According to the procedure shown in Production Example 2, 2-(1,3-dioxan-2-yl)ethyl 6-fluoro-2-(4,6dimethoxypyr imidin-2-yl) oxybenzoate (present compound can be obtained by reacting 2.94 g 'of 2-fluoro- 6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid, 0.44 of sodium hydride in oil and 5.85 g of 2-(bromoethyl)- 1, 3-dioxane.

Production Example According to the procedure shown in Production Example 2, 2-(l,3-dioxan-2-yl)ethyl 2-(4,6-diinethoxypyrimidin-2-yl )oxy-6-phenylbenzoate (present compound can be obtained by reacting 3.52 g of 2-(4,6dimethoxypyrimidin-2-yl)oxy-6-phenylbenzoic acid, 0.44 g v' 20 of sodium hydride in oil aind 5.85 g of 2-(bromnoethyl)- 1,3-dioxane.

Production Example 6 According to the procedure shown in Production Example 2, 2-(l,3-dioxan-2-yl)ethy1 6-methoxy-2-(4,6direthoxypyrimidin-2-yl)oxybenzoate (present compound 1 can be obtained by reacting 3.06 g of 2-methoxy- 6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid, 0.44 g of sodium hydride in oil and 5.85 g of 2-(bromoethyl)- 1,3-dioxane.

Production Example 7 According to the procedure shown in Production Example 2, 2-(l,3-dioxan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-methylbenzoate (present compound (V-34) can be obtained by reacting 2.94 g of 2-(4,6- 10 dimethoxypyrimidin-2-yl)oxy-6-methylbenzoic acid, 0.44 g 0e* of -edium hydride in oil and 5.85 g of 2-(bromoethyl)- 1,3-dioxane.

Production Example 8 According to the procedure shown in Production Example 2, 2-(l,3-dioxan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-trifluoromethylbenzoate (present

U.

compound can be obtained by reacting 2.94 g of 2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-trifluoromethylbenzoic acid, 0.44 g of sodium hydride in oil and 5.85 g of 2-(bromoethyl)-l,3-dioxane.

C

Table 1 illustrates specific examples of the compound which can be produced by using the corresponding starting compounds. Compound (1-12) was prepared according to the procedure of Production Example 1. Compounds (V-14) to (V-23) were prepared according to the procedure of Production 1Example 2. Co'mpounds (111-5), (1-24) and (111-9) were prepared according to the procedure of Production Example 3.

0 to *oft*: 0 t.

.Sg

S

S

V S a S V 5 5 SS S S S VS N a S *55 5*S SO S US 565 S 5 0 S S @5 5 S S U U U S S S S S S Table 1 Compound1 A 1 lI 2J'y3I I i X 1 2J Physical propreties No. 1 1 1 1 R' R refractive index)

CH

2 -KH H H CCI CH OCH 3 3 (3)CH 2 H H H CF OCH 3

OCH

3

CH

2 H H H 0 oCC I OCH3JOCH 3 2 -j H H Hj 0 CBr OCH 3

OCH

3

CH-

2 -1 H H OCH 3

OCH

3 nD 22 1.5318 -Cont'd

*S.

U

4 *SS S 4 4 4 £4 £4 0 0 £0 0 S I C 0. 'ge o £0 6 Table 1 (cont'd) Physical propreties refractive Index) -Cont'd *0 a* aS 0* a5 V S '*a Table I (cont'd) Physical prop.,etles refractive Index)- Cont'd *S4 *ee S SW S* S S *S S S S S S. 455 ofto 55 Table I (donid) Physical propreties refractive Index) Cont'd L &4 9. 9 0 aC 400 S S S o *0 5 0 S S S a *9 *FC ate si S sa so.

S S S 65 0 5~ 5 S S S S V *5 5005 S Table 1 (cont'd) Compound A y2-y3 X 1 2 Physical propreties No. A _R R refractive index) H H 0 CF O0H 3 OCHq H H H 0 CCI OCH 3

OCH

3 (11-3) H H H 0 CH OCH 3 0CH3 n 0 24 1.5355 (14 H H H s CCI OCH 3

OCH

3 (11-5) H H H 0 CBr -OCH 3

OCH

3 (11-6) 4Q5 H H H S 0Br 011CH 3

OCH

3 (11-7) H H H 0 COCHj OCH 3

OCH

3 H H H 0 CCI OCH2 0C1-1 Cont'd S. p p p

S

p *Sp 5 0 p pa p p pp S a 7 p *60: a table 1 (cont'd) Physical propreties refractive index) Contfd 0ee 4*

C

a a a sea S a ~e.

a. a S a 9 a t a' *ac 4.6 be S *e~ .h S 8 S. a ma p 9 sac a a S *9 551g a C C Table 1 (cont'd) Cont'd

.E*

0 0 0 0 0 000 0 :1 0.~0 SO S SI S~0 0 0 S OS S S 55 5 0 5 500 5 5 5 S S S 5 00 S S S S 5 0 Tare I (o~nt'd) Physical propreties" refractive index) Cont'cI

B..

.4 0

B

Se .04 C 4.6 5 S B 54 4. 4 C -B 4 4* 4 o 4 4 *4 64* 4 44 4** 4. 4 C 4 9* C *0 S t *C4 B CS 4 444 C B Table I (cont'd) Compound_ 31 1 2 Physical propreties NO. A Y' L Y 3 X Z R R refractive index)_

CH-

2 H H H 0 CCI OCH 3

OCH

3 (V-26) CH 2

CHCH

2 H H H .o Cc QCH 3

OCH

3 0 (V-27) Ck-;C2H H F 0 CCI OCH 3

QCH

3 (V-28) CH 2

CH

2 H H OCH3 0 C OCH 3

OCH

3

-O

(V-29) CH 2

CH

2 H H H 0 C 13r OCH 3

OCH

3 (V-3 0) CI- 2

CH

2 DH H H;IS CBr OCHg OCH 3 0- (V-31) CH 2

CH

2 H H H 0 COCH 3 0OCH 3 I(V-32) CH 2

CH

2 H H H s~CI M. H ICH 3 -Cont'd- 4 4 S

C

0 4 .4e 5 *Se C S 0**S *5 0 0 C C S 35 40* SO C @5 *5-4~ S S C S S C, CS C IC S C ~e SOC C C S CS C-SCS C C Table 1 (cont'd) Compun 1 2 >3 1 2 177-ysical propreties Copun. Y Y Y R. R refractive index) 14 (V-1 7) C2H DH OH 3 H- CHI OCH 3

OCH

3 nD 1.5215 (V-1 8) CH 2

CH

2 (2 H H H 0 OH CH3 OH3 nD 24 1.5419 (V-1 9) H2H <DH H H 0 OH 00H 3 n D 241.5375

CHH

2 H H H 0 N I00H 3 00H 3 nD 24 1.5193 (V-21) CH2(jH H H 0 N OCH 3 00H 3 n 0 24 .1.5055 (V-22) C2<H H H 0 N OCH 3 I0C.H 3 nD2 1.5190 (V-23) OH 2

CH

2 -O2 H H H 0 Cc OCH 3

OOH

3 nD 24 1 .5243 (V-24) CH 2

H

2 -K H H H 0 CF 00H 3 00H 3 -Cont'd- *6 A 0

A

@00 0

A

0 6 *4 0 4 0 a S A 0 aS 900 Sb 0 46 SeA 6 0 a 0 0 44 0 A 0.0 4 0 6 S 0 A 6 0 S A A S Table 1 (cont'd) Cont'd a a a 4*t a 4 S S 54 4. 4 5 a C 45 4 a a pa ~*a 45 a 5* 454a. a p a 4a 4 5 C S C 4 5 0 a S S Table 1 (cont'd) Physical propreties refractive index) n241.5341 Cont'd *6 6 6 t' 9 06 a 004 *96 46 5 468 S 0 6 U SE C 4 98 6 9 PA. 5 6 5 6 5- 6 4 4 4 6 3 .Tab.le 1 (co ntd) Physical propreties refractive index) Cont'd Aed S. 4

S

S

o 5 5 *SS S S S S 48 *5 5 5 5 a S S S. SOS *4 5 54 ,Se S S 4 0 S SO 0 0 05 O 5 5 S S S S 5 0 0 5 0 5 0 Table I (conVd) Cont t d free 0

S

a V S *00 C S S S *S S. C S a CS C S S C S C. CUt CCC SO S ~e SOd S S S 0 C *S S S *t 0 C S *St S S S S S C S U Table 1 (cont'd) CompoundJ A Y 1 R 2 Physical prcipreties No. refractive index) (111-9)

CH

2 0 H H H '0 CH- OCH 3

OCH

3 nD 251.5332 (111)CH 2 H H H 0 CCF 3

OCH

3

OCH

3 0Ili) C 2

HC

2 H H- H 0 OCH3 OCH 3

OCH

3

CH

2 CH 2 H H

CC

2

H

5

OCH'

3

OCH

3 (111)

(CH

2 5 0~ H H H 0 CCN OCH 3

OCH

3 (111-14)

CHC

2 (Q H H H 0 CN0 2

OCH

3

OCH

3 (lI1)

CH

2 -<rCH H- H H 0. COCH 3 00H 3 0CH 3 (111-16)CH H H H 0 COH OCH 3

OCH

3 -Cont'd e.g 4e a 0 9 a

U

*60 0 0 0 IS 9. 0 0 0 9 S D e *9 *5.

L.a S. SI #0.

S a 0 Si 0 0 #4 0 U *SS 0 0 S 4 5 *S 0 0 S S Table 1 (cont'd) Compound No.

(V-41) (V-42) (V-43) .V-44) (V-46) (V-47) (V-48) y 2 R1 R 3 2 Phsia prpe 2 k~ A zI refractive index)

CH

2

C

2 -0

CH

2

CH

2

CH

2

CH

2

CH

2

CH

2

CH

2 0H 2

H

H

H

H

H

H

H

H

H

H

CCOOCH

3 CC ON (CH, 3 2

OCH

3

OCH

3

OCH

3 00H 3 I I I I I -I

H

H

COC

3 H-17) 00H 3

OCH

3 1 -1 I %I

CC

4

H

9 (n)

OCH

3 0OH 3 1 1 1 1 '1 1-

H

COC 2CHF 2

OCH

3

OCH

3 II~I~I~I I-I--I H I H I H 1

GC

5

H

1 1

OCH

3

OCH

3 I I I I I

H

CSOC

2

H

5

OCH

3 ODCH 3 I I- H I H CS0 2

CH

3

OCH

3

OCH

3 -Cont'cI

**E

S

S

S S

S

55. 5 5 P 55 5* 9 3 S S 55 9 S S S 35 535 55- 5 55 S S 9 55 0 *4 0 S *S3 S S S S S a Table 1 (cont'cl) Compound A Y1 2 .3 x zR R2 Physical propreties No. Y Y XZRR refractive index) (V-49) CH 2 CHa-( H H 'H 0 COCH 3

OCH

3 0 HAC (V-SO) CH 2

CH

2 H H H 0 C~ OCH 3

OCH

3 OD H 0 CH3OCH 3

OCH

3 CHaCH 2 C C 3

OH

CH

2

CH

2 H* H H- 0 C- FOCH, OCH 3 (V-53) HCH 2

CH

2 0 C> H H OCH 3 OCHg (V-54) CH 2

CH

2 H H Ha1C CI 3 00H 3

OCH

3 0

C

2

H

CHCH

2 H H H. 0 00-1- 3

OCH

3 -Cont'd-

A

A

C A asa S C SO 0* 0 S 0 A S A A A S. bAA *5A IA A Rd Re. S S A S A AS 4 @4 A A ASS A 0 S A S S A S A A S A Table 1 (cont'd) Compound 1 2j

R

2 Physical propreties No. A refractive index) (V-57) CHC20C3 H H H -0 CCI OCH 3

OCH

3 (V-58) CH 2 CH 0 CT H -H H 0 CF OCH 3

OCH

3 (V-59) H OH ~-CH 3 H H H cc OC CH (V0)CaC 2 H H H 0 CCI ocHg OCH 3 (V-59) CH 2

CH

2

~-CH

3 H H H 0 CrOH 3

CH

cH3cH2(7<CH H H H S Cor OCH 3

OCH

3 (V-61) CH 2

CH

2 GH H H H 0*oCH OCH 3

OCH

3 (V-64) CH 2

CH

2 <2 5 H H H 0 c COH. I, 1 Production Examples for the compound a starting material, are shown below.

Production Example 9 9.00 Grams of acetylsalycilic acid and 9.95 g of 2-(2-bromoethyl)-l,3-dioxane were dissolved in 100 ml of N,N-dimethylformaide was mixed with 7.60 g of anhydrous potassium carbonate. The resulting solution was stirred at 1200C to 130 0 C for. 3 hours. The reaction solution was poured into diluted hydrochloric acid, and 10 extracted with ethyl acetate. The organic layer separated from the aqueous layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed

S

under reduced pressure, and the residue obtained was distilled under reduced pressure to obtain 10.5 g of 2- (l,3-dioxan-2-yl)ethyl salycilate in a yield of 83%.

a 120 0 C-122°C/0.07 mmHg 24 nD 1.5246 Table 2 illustrates specific examples of the S 20 compound which can be produced by using the ****corresponding starting materials corresponding starting materials.

1' Table- 2 0--A

S.

a 4.# a a~ 9*ee

S

S 550 a *9 a a a.

a a S..

S

a a See.

a S. S OS

S

S

A y y 2 y 3 x Z

CH

2 .1 H. H H S CCI C2H H H 0 N

CH

2 -K4 H H H 0 CF C2H H H 0 CCI

CH

2 -K H H H C) CBr CHa-< H H H 0 CH

CH

2

OH

2 -K H H H 0 OH

CH

2 CH H H H 0 CF CH2CH 2 -K H H H 0 CCI (Tht'ri

S.

9* S S

'S

S a

S

S..

a *5*S .5

S

*5 S S

S

Table 2 (cont'd) A y"I y 2 y 3 X Z

CH

2 0CH 2 H H H S CCI

OH

2

CH

2

CH

2 H H H 0 CBr 0H 2 -Qo H H H 0- OH 0l CH 4 ciH H H 0 OH

CH

2

CH

2

CH

2

CH

2 H H H 0 CCI CH2C2C- H H 0___CH

CH

2

CH

2

CH

2 H H H 0 OHF

CH

2 HCH3~~ H H H 0 OFI CH 3H() H H H 0001I

CH

2 CKf H H H 0 001

H

3

C

H

3 O H H H S OBr CH 2

E

Cont'd Table 2 (cont'd) Cont'd TabW. 2 (cont'd) 3?

U..

U.

OU U ~.ew

S

as ~S S

U

U.,

A y 1 y 2 y 3 x z H H H 0 CCI H H HO OCH 0H H H S CCI -YH H H 0 CBr H H Hi S CBr H H H 0 COCH 3 H H 1-I 0001I OH H H 0 CFI oH H H 0

N

H H H 0 CCF 3 Cont'd .4 0 *4 h.

tests 'd 2 (cont'd) Table 341 66 o 0

C,,

S,

0~ *4

OC

9 0 554 A 1 x2 y x z H H H 0 CCH3 o H H H 0 H H H 0 CN0 2 0 H H H 0 CCI CH2 H H H 0 N CH2-40 H H H 0 CF CH2,-1 H H H 0 CCI CH2 0 H H H S CCI H H H 0 CH CH 0 H H H S CBr H H ~H 0 CH Contd Table 2 (cont'd) 0 S*0 R @0 S S

SOS.

S

0*SS

S.

9 0S

S

0S@ @5@50* SS S 55 5 5 @55 S S. 55 5 5 0

S

S

A Y y 2 z

CH

2 H H H 0OCCI 0 CHa-§ H H H 0 OH Cl2H H H o CCF 3

C,(I

2

C

2

C

2 5 H H H 0 CSCH 3 0-

CH

2

CH

2 -0Q H H H 0 C0 2

H

(CH

2 5 0~7 H H H 0 CON CH2

C

H

2 -CO H H H 0 CN0 2

OH

3

CH

2 -<1f H H H 0OCOCH 3

CH

2 1-YCCH 3 H H H 0OCOH >H H H 0 N 0 >CI H H 0 CF Cont'd- Table 2 (cont'd)

S.

9 S.

0g 00 0 0040 0 0500 4

S..

A ylIY2 y 3 "z -K H CH 3 H 0 CCI -C 0>H H OCH3 S

CCI

H H F OCBr -C C 2 1-1 5 H H S CBr >H Cl H 0 COCH 3 H H F O CCF 3 0 -C IO H H H 0

CCI

CH

3

CH

3 H H H 0 CF H H H 0 CH 0 C 'H3H p CH H H S CCI 0

CH

3 -cx CI H H C0* ont'd- 0c 0 *0 9e Table 2 (co nt'd) *see 0** q 9

S.

se 4 A y 1 y 2 y3x z 0C3H H H S OBr 0 2-5H H H 0OcocH3 C 21-15(n H H H 0 C

,CH

2 CH2 (j H H H 0 OH

OH

2

CH

2 -O H H H 0 OH 0

CH

2 -(j0 H H H 0 CCI 0 0

CH

2 :i H H H 0 CBr 0 0H 2 11H H H S CBr 0 0' 0H 2 JH H H 0 CHON 0 Cont'd Table 2 (cont'd) A I 2 0 CH CH 3

H

0 CH2-(1 H H 0 0H2 H H 0

*CH

2

CH

2 H H A 0@ :boo CHCH-) H H I. 0 *00

CH

2

CH

2 H Cl

-A<

C

2

CH

2 H Cl Cont'd Table 2 (cont'd) A Y 1 y 2 H2

C

OH

2 H H

CHCH

2 H H CH2CH2-(2 H H 9 fe:CHCHCH 1 000 C H 2

H

2 H H

H&SH

Cont'd Table 2 (cont'd) A Y 1

Y

2

CH

2

CH

2 H H

CH

2

CH

2 H H 0 0 r0 e~.CHH-' H H 0 see

CH

2

CH

2 H H

CH

2

CH

2 H H 04* 0 *0

CH

2

CH

2 H H

CH

2

CH

2 N H H 0 Cont'd Table 2 (pont'd) A ly1 y 2

Y,

CH

2

CH

2 H H H

CH

2

CH

2 H H H 0**0 CHCH- H H H C H 2

H

2 H H H 0 go%0H 2 0H 2 F1 H

CH

2 H( H H H S2C

H

2 2 H H H &so 0 0 a 0 Oont'd Table 2 (cont'd) a B* b 0BS as a tB.

0 se A ly 1 y2 y 3 x

CH-

2

C

2 H H o0 2

H

CH

2

CH

2 H H H 0 C-6C 2 0H0H "CH 3 H H H 0 cci

CH

2

CH

2 -<TH H H

CH~QHCH

3 0OH 3 C3 H H H 0 ccI CH 'CH 2

-<O+CH

3 0 3

H-

7 H H HS c

CH

2

CH

2 H. HS

C

CH

2

CH

2

O-H

3 H H H 0 CBr CH2CH2 0<CH3 H H H S OBr 0H 2 021-1K 0 5 H H H 0 COCH 3

CH

2

CH

2 CH()H H H 0 CCI 74 1 Formulation Examples are shown below. In the examples, the present compound is shown by Compound No. in Table 1, and parts are by weight.

Formulation Example 1 Fifty parts of any one of the present compounds (IV-ll), (V-14) and 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate and parts of synthetic hydrated silicon dioxide are well mixed while being powdered to obtain a wettable powder.

10 Formulation Example 2 Ten parts of any one of the present compounds (III-5), (III-7), (III-9), (IV-11), (V-14), (V-17)e (V-21), 15 and 14 parts of polyoxyethylene

I

styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 40 parts of xylene and 30 parts of cyclohexanone are well mixed to obtain an emulsifiable concentrate.

**i 4 4 Formulation Example 3 Two parts of any one of the present compounds (IV-11), (V-14) and 1 part of synthetic hydrated silicon dioxide, 2 parts of calcium lignosulfonate, parts of bentonite and 65 parts of kaolin clay are well pulverized and mixed. The resulting mixture is well 715 1 kneaded with water, granulated and dried to obtain a granule.

Formulation Example 4 Twenty five parts of any one of the present compounds (III-5), (III-7), (III-9), (IV-1i), (I- 13), (Vand 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 10 69 parts of water are mi.xed and wet-pulverized until the 9 9 particle size decreases to 5 microns or less. Thus, a .i9.

suspension formulation is obtained.

That the present compounds are useful as an active ingredient for herbicides is shown by the following test examples. In the examples, the present compound is shown by Compound No. in Table 1, and compounds used for comparison are shown by Compound symbol in Table 3.

6 9 99969* 9 dir oomle

I

Table 3 symbol Structural formula Remarks .9 a..

9.

9 U 9*S9

S

*0@9 99 9 U *9*9 6~*

S

99SU 9* 9. 9

I.

9 9

S

*9 99 9 9 9S.OSS 9

OC

2

H

N00 OC 3

CR

3 N

OCR

3 COO H

CH

N

CR

3 N

OCR

3

COOCH

3

H

N OR N

OCR

3 N~7 OCR 3 0 !I

CR

3 C-0-CR

CR

3 N

OCH

3 EP-0 249 708-Al (Compound No. 1) EP-0 223 406-Al (Compound No. 16) EP-0 223 406-Al (Compound No. 18) EP-0 223 406-Al (Compound No. EP-0 249 708-Al (23 1.5271)

D

4 Cont Id Table 3 (Cont'd)

S.

*99 9.

.9 S Os sq *sss 5 9* S 'A 9** 0 111-

CH

3 N C-0-CH H N CH 3 N 0I 0 COCH3

N

-N

OCH

3 N

OCH

3 0

COH

N

N CH 3 04B 0 11

C-O-CH

2

CH

2 CH C 2

H

5 2 M _,,OCH 3 EP-0 249 707-Al (Compound No. 4) EP-0 249 707-Al (Compound No. 1) EP-0 249 707-Al (Compound No. 8) Comparative Compound (n 24 1.5129)

D

0* 9 9 50 08 'a 'a 9 a *69s*s S S

OCH

3 1 The determination of the herbicidal activity and phytotoxicity was carried out as follows: When the states of emergence and growth of treated test plants (weeds and crops) at the time of determination were completely the same as or hardly different from those of untreated test plants, the value of determination was taken as When the treated test plants were completely killed, or their emergence and growth were completely inhibited, the value of determination was taken as and an interval between and was Go divided into four stages, i.e. and 0*1. The evaluation was thus made in six stages.

S*Test Example 1 Soil surface treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, 4 and seeds of Japanese millet, oats, tall morningglory and velvetleaf were sowed in the respective pots and covered with soil. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water corresponding to liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer. After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined. The results are shown in Table 4.

Table 4 4* 80 4 080 .6 6 0 *0

S

888 -a S I 8**S a.

S

3d).

6 400560 6* 6@ a Os 0O 6 0 0

S

*@60*6

S

Cont Id Table 4 (Cont'd) (1-12) 1.25 (1-13) 5 5 4 3 4 1.25 4 3 3 4 A 5 4 3 0 1 1.25 2 1 0 0 B 5 4 3 0 2 1.2-5 2 1 0 0 C 5 3 3 0 1 1.25 1 2 0 0 so :0.

U U

'U.S

a ee t o *cS a U 4 a.

S

a 1 Test Example 2 Soil surface treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and seeds of velvetleaf were sowed in the zespective pots and covered with soil. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifi,able concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto th& whole soil surface by means of an automatic sprayer. After application, the test plants were cultivated for 19 days in a greenhouse, and the 1 herbicidal activity was examined. The results are shown in Table Table Test Dosage rate of Herbicidal activity compound active ingredient Velvetleaf (V-17) 5 4 A 5 1 a at 'iSO,

U.

*k U S. S .6 CO S U S eva a Test Example 3 Soil surface treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and seeds of Japanese millet, oats and velvetleaf were sowed in the respective pots and covered with soil. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer. After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined. The results are shown in Table 6.

Table 6 Cl em.-' e# r0 r S .r p 0 a Ce S 9- Dosage rate of Herbicidal activity Test active ingredient Ja e tcompound (Japanese Oats Velvetm/a) millet leaf (V-19) 5 4 4 3 5 4 4 4 (V-21) 5 4 4 4 (V-22) 5 5 4 4 (V-23) 5 4 3 3 H 5 2 1 3 1 Test Example 4 Soil surface treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, 5 and seeds of Japanese millet were sowed in the respective pots and covered with soil. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer. After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined. The results are shown in Table 7.

Table 7 ::0 @0 s

S..

@0 000 @0 040094 a 1, 06 0

S

5.

p 50 4 4.

Test Dosage rate of Herbicidal activity compound active ingredient Japanese millet 0.31 4 (III-7) 0.31 4 0.31 4 (1-13) 0.31 4 D 0.31 3 E 0.31 1 F 0.31 2 1 Test Example 5 Foliar treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, 5 and seeds of Japanese millet, oats, radish, velvetleaf and tall morningglory were sowed in the respective pots and cultivated for 8 days in a greenhouse.

Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with a spreading agentcontaining water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer.

After application, the test plants were cultivated for .4.

6*4 0O a 0*e Se

S

S..

S

SOS 0 5 Sues a.

S. S a 0 *5 S S 0

~.SSS.

1 19 days in a greenhouse, and the herbicidal. activity was examined.

The results are shown in Table B.

Table 8 Test Dosage Herbicidal activity corn- rate of pound active Japanese Oats Radish Velet Tall ingredient millet leaf morningglory 5 5 5 4 5 4 5 5 4 4 5 4 (11-3) 5 4 5 4 3 3 5 5 4 4 5 (111-5) 5 4 4 3 5 3 5 5 4 5 5 4 (111-7) 5 5~ 5 5 4 5 4 (111-9) 5 5 4 4 4 4 5 5 5 4 5 4 (IV-ll) 5 4 4 3 4 3 (1-12) 5 4 5 5 4 3 (1-13) 5 5 5 5 5 4 A 54 2 1 1 2 B 5 3 3 1 1 1 C 5 3 2 2 1 2 1 Test Example 6 Foliar 'treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and seeds of Japanese millet, oats, radish and velvetleaf were sowed in the respective pots and cultivated for 8 days in a greenhouse.

Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation 10 Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with a spreading agentcontaining water corresponding to 10 liters/are and unie formly applied from above onto the whole foliar portion 9 of the test plants by means of an automatic sprayer.

After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was 9 examined.

The results are shown in Table 9.

eqe 0 4 S ar Table 9 Dosage Herbicidal activity Test rate of compound active ingredient Japanese Velvetmillet Oats Radish leaf (V-19) 5 4 4 3 4 5 5 5 5 (V-21) 5 5 5 5 (V-22) 5 5 5 5 (V-23) 5 4 3 5 E 5 2 2 2 2 goo* to 0.

#0 9r US 59

S.

a swaO 1 Test Example 7 Foliar treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and seeds of tall morningglory were sowed in the respective pots and cultivated for 8 days in a greenhouse.

Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with a spreading agentcontaining water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer.

After application, the test plants were cultivated for 06

C

*6.

*e bb 9 9 S. S p 1 19 days in a greenhouse, and the herbicidal activity was examined.

The results are shown in Table Table Test Dosage rate of Herbicidal activity compound active ingredient Tall morningglory (1-24) 1.25 4 J 1.25 1 Test Example 8 Foliar treatment test in upland field 5 soil Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and seeds of Japanese millet, oats and radish were sowed in the respective pots and cultivated for 8 days in a greenhouse.

Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with a spreading agentcontaining water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer.

After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined.

The results are shown in Table 11.

Table 11 Ca a

C.*

S.

C

*4Ce a r a.

a. 9 Dosage rate Lf Herbicidal activity Test active ingredient compound Japanese Oats Radish millet 0.31 4 4 4 (1-13) 0.31 4 4 4 0.31 4 4 4 (V-21) 0.31 4 4 4 (V-22) 0.31 4 4 4 F 0.31 1 1 1 J 0.31 2 2 2 Test Example 9 Foliar treatment test in upland field soil Cylindrical plastic pots of 10 cm in diameter 5 and 10 cm in depth were filled with upland field soil, and seeds of Japanese millet were sowed in the respective pots and cultivated for 8 days in a greenhouse.

Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with a spreading agentcontaining water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion

V

0 4. a.

*boo*: aC a a. a 0 0 00 0 *000 0 0ss o 9r 0

S

S~

S.

0r 0 1 of the test plants by means of an automatic sprayer.

After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined.

The results are w..n in Table 12.

Table 12 Test Dosage rate of Herbicidal activity compound active ingredient Japanese millet (V-10) 0.08 4 D 0.08 2 G 0.08 2 Test Example 10 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in'area and 11 cm in depth were filled with upland field soil, and seeds of soybean, cotton, corn, velvetleaf, black nightshade, barnyardgrass, giant foxtail and johnsongrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example I, and the prescribed amount of each emulsifiab3e concentrate was diluted with water corresponding to liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer.

1 After application, the test plalats were cultivated for 18 days in a greenhouse, and the herbicida3. activity and phytotoxicity were examined.

The results are shown in Table 13.

U.,

a.

a 9 a 9*@U

S.

U a *.e 4a a S. CU

U

a. a

U.

a CC

C

a C U w 4 4 4 4.

4 0 0 0 0 *4 0 4 4 44 4 S S S *0 0.0 400 @0 4 00 Os.

S *4 0 4 @4 4 S a eQS S 4 0 S S 0 S 0 0 S Table 13 Dosage rate Phytotoxicity Herbicidal activity Test of active compound ingredient Soy- Cotton Corn Velvet- Black Barnyard- Green Johnsonbean leaf nightshade grass foxtail grass 5 1 J 0 1 4 5 5 5.4 2.25 1 j 0 0 3 5 4 4 4 (11-3) 0 0 4 4 4 4 4 1.25 0 0 03 4 333 (111-5) 5 0 0 1 3 4 4 4 4 (111-7) 5 1 1 1 3 4 4 4 I(V-8) 1 1 1 4 5 5 4 4 (111-9) 5 0 1 1 3 4 4 5 4 (1-12) -5 1 1 1 4 5 5 5 1.25 1 0 0 3 5 4 4 4 A 2 2 0 0 0 2 1 3 S 1.25 0 2 0 0 0 1 0 2 0 0 0 0 0 -1 1 0 1.25 0 0 0 0. 0 1 1 0 H 5 0 0 0 2 2 0- 1 0 1 Test Example 11 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of cotton, black nightshade and sicklepod were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifi- 10 able concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

:The results are shown in Table 14.

Table 14 Table 14 o* 69 *S

S

S

a ~9 Dosage Phyto- Herbicidal activity Test rate of toxicity compound active ingredient Cotton Black Sicklepod nightshade (V-23) 5 0 5 4 D 5 3 4 0 H 5 0 2 1 9 1 Test Example 12 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of soybean, cotton, corn, back nightshade and johnsongrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each 10 emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table

T

:o Table

S

S

Dosage Phytotoxicity Herbicidal activity Tes rate of com- active pound ingre- Soy- Cotton Corn Black Johnson dient bean nightshade grass (g/a) (V-21) 2.5 0 1 0 4 4 A 2.5 1 2 0 0 3 B 2.5 0 0 0 0 2 C 2.5 0 0 0 0 0 1 Test Example 13 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of cotton, back nightshade, barnyardgrass, giant foxtail and, johnsongrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed 10 amount of each emulsifiable concentrate was diluted with e* water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

*The results are shown in Table 16.

T* 16 Table 16 54 *4 Dosage Phyto- Herbicidal activity Test rate of toxicity com- active pound ingre- Black Barn- Giant Johnsondient Cotton night- yard- foxtail grass shade grass 5 0 4 4 4 4 (IV-11) 5 0 4 4 4 4 A 5 2 0 2 1 3 C 5 0 0 1 1 0 1 Test Example 14 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of soybean, black nightshade and giant foxtail were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifi- 10 able concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil o surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 17.

Table 17 .4 0 *0 a S.

a* 64 6eO@ a4

U.

Dosage Phyto- Herbicidal activity Test rate of toxicity compound active ingredient Soybean Black Giant nightshade foxtail 5 1 4 5: 1 4 4 (V-18) 5 0 4 3 (V-19) 5 0 4 3 5 1 4 3 (V-21) 5 0 4 4 (V-22) 5 1 4 4 (1-24) 5 1 5 3 B 5 0 0 3 H 5 0 2 1 1 Test Example 15 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of soybean, barnyardgrass, giant foxtail and johnsongrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied p.

tC ep .4 q WGCt .4 d 4 1 onto the whole soil surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 18.

Table 18 Dosage Phyto- Test rate of Herbicidal activity com- active toxicity pound ingredient Soybean Barnard- Giant Johrnsongrass foxtail grass 2.5 1 3 4 3 (IV-1l) 2.5 0 3 4 3 (1-12) 2.5 1 4 4 4 (1-13) 2.5 1 3 4 3 F 2.5 1 0 2 2 Test Example 16 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled'with upland field soil, and seeds of corn, black nightshade and giant foxtail were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifi- Ji. 0@~ *t J q 4 h a

CC

49C C C S CO 9

I

5.

1 able concentrate was diluted with water corresponding to liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 19.

Table 19 Dosage Phyto- Herbicidal activity Test rate of toxicity compound active ingredient Corn Black Giant nightshade foxtail (1-13) 5 1 4 4 (V-22) 5 0 4 4 (1-24) 5 0 5 3 A 5 0 0 1 Test Example 17 Soil treatment test in upland field soil ,0 Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of soybean; cotton, corn, giant foxtail and johnsongrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water 1 correspon6ing to 10 liters/are and uniformly applied onto 'the whole soil surface by means of an automatic sprayer.

After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table Table i HDosage Herbicidal Test rate of Phytotoxicity activity com- active pound ingredient Soy- Cotton Corn Giant Johrnsonbean foxtail grass 0 see 0.63 0 0 0 4 4 E 0.63 0 0 0 2 2 Test Example 18 Foliar treatment test in upland field a soil Vats of 33 x 23 cm 2 in area and 11 cm in depth S were filled with upland field soil, and seeds of cotton, corn, tall morningglory, velvetleaf, black nightshade, sicklepod, barnyardgrass, giant foxtail and johnsongrass were sowed in the respective vats and cultivated for 16 days. Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and tbh prescribed amount of each emulsifiable concentrate was diluted with water corresponding to 1 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer. The conditions of growth of the weeds and crops at that time varied depending upon the kind of the test riants, but the test plants were in the to 4-leaf stage and were 5 to 30 cm in height.

Eighteen days after application, the herbicidal activity and phytotoxicity were examined. The results are shown in Table 21. This test was carried out in a greenhouse 10 through the whole test period.

3

*O*

0** c S .o.?o o•8oo off' o-2

S

a a S B ~jW a. a a 5-a 9 S a a 96 5.5 50. 05 Os S S a S a *5 S S S a See S C r S S a C Table 21 Dosage Phytotoxicity Herbicidal activity Test rate of Tl lc corn- active Tal Blackt ih- ik Bryr- in Jhsn pound ingredi- Cotton Corn morning Vevt nih-Sc-Bry d-Gat ons ent glory leaf shade lepod grass foxtail grass 1.25 1 0 4 5 5 4 4 4 4 0.31 1 0 4 4 5 3 4 4 4 0.31 1 1 3 4 5 4 3 4. 4 (111-5) 1.25 1 0 4 5 5 5 4 j4 4 (111-7) 1.25 1 1 3 4 5 3 5 (1 9) 1.25 1 0 4 4 4 4 4 4 0.31 1 0 4 4 4 3 4 4 1.25 1 1 3 5 5 4 4 A 1.25 0 0 0 4 1 2 0 2 0.31 0 0 01 0 3 0 1 0 0 B 1.25 0 0 0 1 3 2 1 0 1 0.31 0 0 0 1 3 1 0 0 0 D 1.25 2 2 0 1, 2 0 2 0 0.31 1 0 0 0 2 0 2 03 1_ 1 Test Example 19 Foliar treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of soybean, cotton and tall morningglory were sowed in the respective vats and cultivated for 16 day Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was 10 diluted with water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer. The conditions of growth of the weed and crops *o at that time varied depending upon the kind of the test plants, but the test plants were in the 0.5- to 2-leaf Istage and were 10 to 20 cm in height. Eighteen days after application, the herbicidal activity and phytotoxicity were examined. The results are shown in Table 22. This test was carried out in a greenhouse through the whole test period.

Table 22 Dosage rate Phytotoxicity Herbicidal Test of active activity compound ingredient Tall Soybean Cotton morn morningglory (1-24) 0.63 1 0 4 G 0.63 5 4 2 H 0.63 4 3 3 J 0.63 3 2 3 /O3 1 Test Example 20 Foliar treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of cotton, tall morningglory, sicklepod, giant foxtail and johnsongrass were sowed in the respective vats and cultivated for 16 days. Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of 10 each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer. The conditions i"q of growth of the weeds and crop at that time varied depending upon the kind of the test plants, but the test plants were in the 0.5- to 2.5-leaf stage and were 5 to *9 15 cm in height. Eighteen days after application, the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 23. This test was carried out in a greenhouse through the whole test period.

46m 4 Table 23 Dosage Phyto- Herbicidal activity Test rate of toxicity com- active pound ingre- Cotton Tall Sick- Giant Johnsondient morning- lepod foxtail grass glory 1.25 1 4 4 4 4 (III-9) 1.25 1 4 4 4 F 1.25 2 3 3 1 3 0 1 Test Example 21 Foliar treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of velvetleaf, barnyardgrass, giant foxtail and johnsongrass were sowed in the respective vats and cultivated for 16 days. Thereafter, the test compounds **0 were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of 10 each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer. The conditions of growth of the weeds at that time varied depending upon the kind of the test plants, but the test plants were in the 1- to 2.5-leaf stage and were 5 to 15 cm in height. Eighteen days after application, the herbicidal 105 1 activity was examined. The results are shown in Table 24. This test was carried out in a greenhouse through the whole test period.

Table 24 Dosage Herbicidal activity Test rate of com- active pound ingre- Velvetleaf Barnyard- Giant Johnsondient grass foxtail grass (g/a) (1-13) 5 5 5 5 A 5 0 2 0 2 e 9

I

*S

1 9 *4 d Test Example 22 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seU7A of wheat, pale smartweed, cleavers, chickweed: birdseye speedwell, field pansy, downy brome, wild oat, blackgrass and annual bluegrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer. After application, the test plants 1 were cultivated for 25 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table as a 0 We

S

S

S 5-

S

S S

A.

*5 5 S S S S C *S* 55 4 *e bern S S. C S *S S S .5 S SC. S C S S U S S S S S S Table Dosage Phyto- Herbicidal activity Test rate of toxi- corn- active cit Birds-Ana pound citye Pale riaesChick- eye Field Downy Wild Black-Ana dient f lsmart-Cevr weed speed- pansy brome oat grass grass Wheat weed wellgrs 5 0 4 5 4 4 34444 1.25 0 4 3 3 4 3 4 3 4 4 5 1 4 5 4 5 5 5 4 4 4 1.25 1 3 4 3 5 4 5 3 3 4 (1 9) 5 0 4 3 4 4 4 5 4 4 4 1.25 0 4 3 3 -4 3 4 4 3 4 (V1 5 0 4 3 4 5 4 5 4 4 4 (Vl) 1.25 0 4 3 3 5 3 5 4 3 4 (1-12) 51 4 5 5 5 4 5 4 4 4 1.25 0 4 4 4 5 4 3 3 4 4 A 5 3 2 2 0 30 0 2 3 3 1.25 1 0 0 0 0 0 0 0 2 3 B 5443 4 0 4 4 3 1.25 1 2 3 3 3 0 0 2 2 3 C 1 0 1 1 2 1 2 J333 1.25 0 0 0 0 1 00 ji 1 2 1 Test Example 23 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of beet, pale smartweed, downy brome and annual bluegrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. T e test comDounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each 10 emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied onto the whole soil surface by means of an automatic sprayer. After application, the test plants were cultivate( for 25 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 26.

***Tab Table 26 *e 0* o 5 r r "1

SO

S

S

S

Dosage Phyto- Test rate of Herbicidal activity com- active toxicity pound ingredient Beet Pale Downy Annual (n/a smartweed brome bluegrass (g/a) (IV-ll1 1.25 1 4 5 4 (V-22) 0.63 1 4 4 4 H 2.5 3 1 2 3 1 Test Example 24 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of wheat and annual bluegrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was 10 diluted with water corresponding to 10 liters/are and 4 uniformly applied onto the whole soil surface by means of an automatic spraye After application, the test *4 plants were cultivated for 25 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 27.

Table 27 Table 27 SS 0

S

S

9 Test Dosage rate Phyto- Herbicidal activity com- of active toxicity pound ingredient d Wheat Annual bluegrass 0.31 0 4 (11I-7) 0.31 0 4 0.31 0 4 G 0.31 2 0

I

1 Test Example 25 Soil treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of wheat, birdseye speedwell, downy brome and annual bluegrass were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm. The test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each 10 emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied gas$ onto the whole soil surface by means of an automatic sprayer. After application, the test plants were cultivated for 25 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 28.

Table 28 4 4.

4 S Test Dosage Phyto- Herbicidal activity com- rate of toxicity pound active d ingave Wheat Birdseye Downy Annual dient speed- brome bluegrass well 1.25 0 4 4 4 1.25 0 4 4 4 1.25 0 4 4 4 (V-19) 2.5 0 4 4 4 4 4 0 3 1.25 1 3 0 1.25 1 3 0 3 1 Test Example 26 Foliar treatment test in upland field soil Vats o 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of pale smartweed, cleavers, chickweed, birdseye speedwell, field pansy, downy brome, wild oat, blackgrass and annual bluegrass were sowed in the respective vats and cultivated for 31 days. Thereafter, the test compounds were formulated into emulsifiable concentrates according 10 to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test r* plants by means of an automatic sprayer. The conditions of growth of the weeds at that time varied depending upon the kind of the test plants, but the test plants were in the 1- to 4-leaf stage and were 3 to 25 cm in height. Twenty-five days after application, the 0 herbicidal activity was examined. The results are shown in Table 29. This test was carried out in a greenhouse through the whole test period S* through the whole test period.

S**

to 0

S

0 00 0 090 9 0 8 0 06 *9 3 S 6 4 S0 0 9 0 S *0 *.O 0.8 90 0 94 S*D 4* 0 8 0 6 .0 9 0 08 0 S 8 005 0 6 U 8 S *895 e 0 8 0 Table 29 Dosage Herbicidal activity Test Jrate of corn- active pound ingredi- Dale Cleavers Chick- Birdseye Field Downy Wild Black- Annual ent smart- weed speed- pansy brome oat grass blueweed well grass 2.5 5 4 4 J 5 5 4 4 5 2.5 4 4 3 4 4 3 4 4 2.5 5 4 3 4 4 4 4 4 4 (111-9) 2.5 4 4 4 4 3 4 4 4 4 (1-12) 2.5 5 3 3 4 4 5 54 3 A 2.5 2 3 1 3 0 3 3 3 3 B I 2.5 3 0 1 3 0 3 3 3 2 0 1 1 0 0 0 0 1 0 1 Test Example 27 Foliar treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of pale smartweed, chickweed, birdseye speedwell, field pansy, downy brome, wild oat, blackgrass and annual bluegrass were sowed in the respective vats and cultivated for 31 days. Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation 10 Example 2, and the prescribed amount of each emulsifi- 4* able concentrate was diluted with water corresponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants by means of an automatic sprayer. The conditions of growth of the weeds at that time varied depending upon the kind of the test plants, but the test plants were in the 1- to 4leaf stage and were 3 to 25 cm in height. Twenty-five days after application, the herbicidal activity was examined. The results are shown in Table 30. This test was carried out in a greenhouse through the whole test S4 period.

a a .me

C

a a.

at a S C a S as a. a 1~ S 4* S C S a *.4 eta 'a a ta sea em a a 0 C 54 a a. 4 a a eaQ a a a a a as a t S Table 1 0 Herbicidal activity Test Dosage rate corn- of active pound ingredient Pale Chickweed Birdseye Field Downy Wild Black- Annual smart- speed- pansy brome oat grass blueweed well grass (V-21) 0.16 5 5 4 5 4 4 4 4 (V-22) 0.64 5 5 5 4 4 4 3 F 0.16 3 3 3 3 0 1 1 2 J 0.16 1 0 2 2 2 1 1 2 I ,S 1 Test Example 28 Foliar treatment test in upland field soil Vats of 33 x 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of wheat, pale smartweed, cleavers, downy brome and annual bluegrass were sowed in the respective vats and cultivated for 31 days. Thereafter, the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each 0* 10 emulsifiable concentrate was diluted with water corre- 0e sponding to 10 liters/are and uniformly applied from above onto the whole foliar portion of the test plants 6 by means of an automatic sprayer. The conditions of growth of the weeds and crop at that time varied depending upon the kind of the test plants, but the test plants were in the 2- to 4-leaf stage and were 5 to cm in height. Twenty-five days after application, the herbicidal activity and phytotoxicity were examined.

The results are shown in Table 31. This test was carried out in a greenhouse through the whole test i S* period.

98900 Table 31 Test Dosage Phyto- Herbicidal activity com- rate of toxicity pound active ingre- Pale Downy Annual dient Wheat smart- Cleavers brome blueweed grass 0.31 1 4 4 4 4 0.63 1 4 3 4 4 H 0.63 2 3 1 1 2 J 0.63 2 3 3 3 2 too 0*

*S*

1 Test Example 29 Flooding treatment test in paddy field Cylindrical plastic pots of 8 cm in diameter and 12 cm in depth were filled with paddy field soil, and seeds of barnyardgrass and bulrush were sowed 1 to 2 cm deep under the soil surface. After creating a state of paddy field by flooding, a tuber of arrowhead was 0 buried 1 to 2 cm deep under the soil surface and cultivated in a greenhouse. After 6 days (at the initial stage of generation of every weed), the test 10 compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with ml of water and applied onto the water surface.

After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined. The results are shown in Table 32.

k I 1 11 Table 32 A.0 4 a** .9 4 060 a Dosage rate Herbicidal activity Test of active comlpounld inrdet Barnyard Arrowg/)grass Bluh head 0.63 5 5 3 0.63 5 3 4 0.63 5 3 3 0.63 4 3 4 (1-)0.63 4 4 4 0.63 4 3 4 (IV-ll) 0.63 5 3 3 (1-12) 0e_63 4 4 4 (1-13) 0.63 44 4, A 0.63 4 1 3 B 0.63 2 0 3 C 0.63 3 0 3 E 0.63 1 0 1 F 0.63 2 2 2 G 0.63 2 1 2 e9 4* ~a b 4 @4 0 4 4 0 4 1 Test Example 30 Flooding treatment test in paddy field Wager's pots of 200 cm 2 were filled with paddy fieLd soil, and seeds of barnyardgrass and broadleaf weeds (iae. false pimpernel., indian toothcup, water wort and red stem [Amn.4 spp.1) were sowed 1 to 2 cm deep under the soil surface. After creating a, state of paddy field by water flooding, tubers of ar~rowhead and water I I 'I 1 nutgrass were buried 1 to 2 cm deep under the soil surface. Also rice "eedlings of 2-leaf stage were transplanted into tie pots. The weeds and crops were cultivated in a greenhouse. After 4 days (at the initial stage of germination of barnyardgrass), the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, a prescribed amount of each of the emulsifiable concentrates was diluted with 10 ml of water and applied onto the water surface in the pots. Water leakage decresing the depth of flooding water by 3 cm was carried out on the day

*A

subsequent to and two days after the application of test compounds. The depth of flooding water in each pot was recovered and kept at 4 cm, while the test plants were a cultivated for 20 days in a greenhouse. Then, the herbicidal activity and phytotoxicity was examined. The results are shown in Table 33.

Table 33 9* 4) 0

V

bo a *1* Dosage Phyto- Herbicidal activity Test rate of toxicity com- active ound ingre- Barn- Broad- Arrow- Water pound ingre- R dient Rice yard leaf head nutgrass weeds grass 0.16 0 4 4 4 4 (III-7) 0.16 0 3 5 3 3 A 0.16 0 0 0 1 0 B 0.16 0 0 0 0 0 C 0.16 0 0 0 0 0 t/f 1 Test Example 31 Flooding treatment test in paddy field Wager's pots of 200 cm 2 were filled with paddy field soil, and seeds of barnyardgrass and broadleaf weeds false pimpernel, indian toothcup, water wort and red stem [Ammannia spp.]) were sowed 1 to 2 cm deep under the soil surface. After creating a state of paddy field by water flooding, tubers of arrowhead and water nutgrass were buried 1 to 2 cm deep under the soil surface. The weeds were cultivated in a greenhouse.

After 11 days (at the 2-leaf stage of barnyardgrass), the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, a prescribed amount of each of the emulsifiable concentrates was diluted with 10 ml of water and applied onto the water surface in the pots. Water leakage decreasing the depth of flooding water by 3 cm was carried out on the day subsequent to and two days after the application of test compounds. The depth of

*R

flooding water in each pot was recovered and kept at 4 e* 20 cm, while the test plants were cultivated for 20 days in a greenhouse. Then, the herbicidal activity was examined. The results are shown in Table 34.

Table 34 Dosage Herbicidal activity Test rate of cor- active pound ingre- Barnyard Broad- Arrow- Water pound ingredient grass leaf head nutgrass weeds 0.63 4 3 3 4 0.63 5 4 4 3 (III-7) 0.63 4 4 3 3 (III-9) 0.63 4 3 4 3 A 0.63 1 0 2 0 C 0.63 0 0 0 0

'S

r 5 5

S

S

4

S

Su

S

SS

S

1 Test Example 32 Flooding treatment test in paddy field Wager's pots of 200 cm 2 were filled with paddy field soil, and seeds of barnyardgrass and broadleaf weeds false pimpernel, indian toothcup, water wort and red stem [Ammannia spp.]) were sowed 1 to 2 cm deep under the soil surface. After creating the state of paddy field by water flooding, tubers of arrowhead were buried 1 to 2 cm deep under the soil surface. Also rice seedlings of 2-leaf stage were transplanted into the pots. The weeds and crop were cultivated in a greenhouse. After 11 days (at the 2-leaf stage of barnyardgrass), the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, a prescribed amount of each of the 1 emulsifiable concentrates was diluted with 10 ml of water and applied onto the water surface in the pots.

Water leakage decresing the depth of flooding water by 3 cm was carried out on the day subsequent to and two days after the application of test compounds. The depth of flooding water in each pot was recovered and kept at 4 cm, while the test plants were cultivated for 20 days in a greenhouse. Then, the herbicidal activity and phytotoxicity was examined. The results are shown in Table 6.6.

o". o 6*e* potr 0 6 S S 04

S.

Table Dosage Phyto- Herbicidal activity Test rate of toxicity com- active pound ingre- Rice Barn- Broadleaf Arrowdient ce yard weeds head _grass 0.31 1 5 4 4 (III-7) 0.31 0 4 4 3 (III-9) 0.31 1 4 3 4 A 0.31 0 0 0 2 J 0.31 0 1 0 0

Claims (1)

122- TJHE CIWM9 DEFXNTNG TIIE XNVENTXoN NRE AS V'OLLOW$: 1. A pyrimidine derivative having the formula, y3 z COP. y2() yi N R N R wherein A is C 3 -CS cycloalkyl Cj-C 6 alkyl, C 3 -C 8 V. I **cycloalkyl Cl-C 6 alkyl substituted with at least one member selected from the group consisting of C 3 C 6 alkyl and halogen, C~ -C 6 oxacycloalkyl, C 3 -C 6 oxacycloalkyl substituted with at least one member selected from the group consisting of C 1 -C 6 alky. and halogen, C 3 C 6 oxacycloalkyl C 1 -C 6 alkyl, C 3 -C 6 oxacyclo- 4 alkyl C 1 -C 6 alkyl substituted with at least one member ,selected from -the group consisting of C -C 6 alkyl and *41 G halogen, C -C 5 dioxacycloalkyl, C 3 -C 5 dioxacycloalkyl substituted with at least one member selected from the group consisting of C I- C 6 .alkyl and halogen, C 3 C 5 dioxa- cycloalkyl C 1 -C 6 alkyl or C 3 C 5 dioxacycloalkyl C1-C6 alkyl substituted with at least one member selected from the group consisting of C C alkyl and halogen; each of R1 and R 2 which may be the same or differnt, is CI-C 6 alkyl, CI-C 6 alkoxy, halo Cl-C 6 alkoxy or halogen; X is oxygen or sulfur; Z is iiitrogen or Cy4; each of Y1, Y2 and y3, which may be the same or different, is hydrogen, halogen, Cl-C 6 alkyl or Cl-C 6 alkoxy; and Y4 is hydrogen, hydroxyl, mercapto, nitro, halogen, Cj-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cl-C 6 5g.alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, halo Cl-C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 1 -C 6 alkoxy, halo C 3 -C 6 alkenyloxy, halo C 3 -C 6 alkynyloxy, Cl-C 6 alkoxy Cj-C 6 alkyl, C 3 -C 6 alkenyloxy C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy Cl-C 6 alkyl, cyano, formyl, carboxyl, Cj*-C6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, phenyl, phenyl substituted with at '~'*least one member selected from the group consisting of e~gCj.-C 6 alkyl, Cl-C 6 alkoxy, halo C 1 -C6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, phenoxy, pheno-&y substituted with at least one member selected from the group consisting Of Cl-C 6 alkyl, Cl-Cs alkoxy, halo C 1 -C 6 S alkyl, CI-C6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected from the group consisting of Cl-Cs alkyl, Cl-Cs alkoxy, halo Cj-C 6 alkyl, Cl-C 6 alkoxycarbonyl and halogen, benzyloxy, benzyloxy substituted with at least one member selected from the group consisting of Cl-C 6 I I I alkyl, C 1 -C 6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxy- carbonyl and halogen, benzylthio, benzylthio substituted with at least one mem-ber selected f rom group consisting Of Cl-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkyl, C 1 -C 6 alkoxycarbonyl and halogen, wherein each of R5 and3 R6, which m~y be the same or different, is hydrogen, Cl-C 6 alkyl, C 3 -C 6 alkenyl or C3-C6 alkynyl, R 6 k. 0, ozi wherein R5 and R 6 are as defined above, -S R 7 wherein R7 is Cl-C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl and m, is an integer of 0, I or 2, 0 -X -C-R7 wherein X1 is oxygen or sulfur, and R 7 is as defined above, or 125 CH2 S R7 II (0)m wherein R 7 and m are as defined above, and n is an integer from 1 to 4. 2. A pyrimidine derivative according to Claim 1, wherein A is C 3 -C s dioxacycloalkyl C 1 alkyl. 3. A pyrimidine derivative according to Claim 2, wherein A is (1,3-dioxolane-2-yl) alkyl or (1,3- dioxan-2-yl) C 1 -C 6 alkyl. 4. A pyrimidine derivative according to Claim 3, wherein A is (1,3-dioxolane-2-yl)ethyl or (l,3-dioxan-2- yl)ethyl. A pyrimidine derivative according to Claim 1, wherein each of R 1 and R 2 which may be the same or different, is C 1 -C alkoxy. 6. A pyrimidine derivative according to Claim 2, 20 wherein both R 1 and R 2 are methoxy. 7. A pyrimidine derivative according to Claim 1, wherein X is oxygen. 8. A pyrimidine derivative according to Claim 1, wherein Z is nitrogen or CY 5 wherein Y 5 is hydrogen, 25 halogen, halo C 1 -C 6 alkyl, C 1 alkyl, C 1 -C alkoxy, phenyl Sor phenyl substituted with at least one member selected from the group consisting of CI-C 6 alkyl, alkoxy, halo C 1 -C alkyl, C.-C 6 alkoxycarbonyl and halogen. 9. A pyrimidine derivative according to Claim 3, wherein Z is nitrogen, CH, CF, CC1, CBr or CI. A pyrimidine derivative according to Claim wherein Z is CF, CC1, CBr or CI. 126 11. A pyrimidine derivative according to Claim 1, wherein both Y 1 and Y 2 are hydrogen or fluorine, and y 3 is hydrogen, fluorine or C1-C, alkoxy. 12. A pyrimidine derivative according to Claim 2, wherein both R 1 and R 2 are methoxy, and X is oxygen. 13. A pyrimidine derivative according to Claim 3, wherein both R 1 and R 2 are methoxy, and X is oxygen. 14. A pyrimidine derivative according to Claim 4, wherein both R 1 and R 2 are methoxy, and X is oxygen. 15. A pyrimidine derivative according to Claim 8, wherein both R I and R 2 are methoxy, and X is oxygen. 16. A method for producing a pyrimidine derivative as defined in Claim 1 which comprises reacting a compound having the formula, 0 Y3 C-O-A y2 X (2) 20 Y 1 Swherein A is C 3 cycloalkyl C,-C 6 alkyl, C 3 -C cycloalkyl C-C, alkyl substituted with at least one member selected from the group consisting of C.-C 6 alkyl and halogen, C 3 -C, S 25 oxacycloalkyl, C 3 -C 6 o a 127 oxadycloalkyl substituted with at least one member selected from the group consisting of C 1- C 6 alkyl and h~alogen, C 3 -C 6 oxacycloalkyl C 1 -C 6 alkyl, C 3 -C 6 oxacycloallkyl C 1 -C 6 alkyl substituted with at least one member selected from the group consisting of C 1 C 6 alkyl and halogen, C 3 -C 5 dioxacycloalkyl, C 3 -C 5 dioxacycloalkyl suh-stituted with at least one member selected from the group consisting of C 1 -C alkyl. *and halogen, C -C 5 dioxacycloalkyl C -C 6 alkyl or C dioxacycloalkyl C 1 -C 6 alkyl substituted with at least too one memblr selected from the group consisting of CC atS 6..Callyl and halogen; X is oxygen or sulfur; Z is nitrogen or CY; each of Y 1 "Y 2 and Y 3 which may be the same agog or different, is hydrogen, haltogen, C 1 -C 6 alkyl or C 1 C 6 alkoxy; and Yis hydrogen, hydroxyl, inercapto, nitro, halgen, C 1 -C 6 alkyl, C 2 P 6 alkenyl, C 2 C 6 alkynyl, C i- C 6 alkyoxy, C Calkenyloxy, 3 6C alkynyloxy, halo C -C 6 alkyl, halo C -C 6 alkernyl, halo C -C 6 alkynyl, halo C -C 6 alkoxy, halo C 3 -C 6 alkenyloxy, halo C 3 -C 6 alkynyloxy, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 3-C 6 alkenyloxy C 1 C 6 alkyl, C3-C6 alkynyloxy C C 6 alkyl, cyano, formyl, carboxyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 a3kenyloxycarbonyl, C 3 -C 6 k V alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of C 1 -Cs alkyl, CI-C6 alkoxy, halo C 1 -Cs alkyl, C 1 -C 6 alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl, Ci-C 6 alkoxy, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl, C 1 -Cs alkoxy, halo C 1 -C6 alkyl, C 1 -Cs alkoxycarbonyl and halogen, benzyloxy, benzyloxy substituted with at least one member selected from the group consisting of C 1 -Cs alkyl, Cl-Cs alkoxy, halo Ci-C6 alkyl, C1-Cs alkoxy- carbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group consisting of Cl-C6 alkyl, C 1 -Cs alkoxy, halo Ci-Cs alkyl, C 1 -C 6 alkoxycarbonyl and halogen, R -N NR6 0 wherein each of RS and R 6 which may be the same or 0:000: different, is hydrogen, Ci-Cs alkyl, C 3 -Cs alkenyl or C 3 -C6 alkynyl, 0 RI -C N R 6 SR6 wherein R5 and R6 are as defined above, -S R 7 11 M wherein R7 is Cl-C6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl and m is an integer of 0, 1 or 2, 0 -X1 -C R wherein X1 is oxygen or sulfur, and R 7 is as defined above, or -tCH 2 S R 7 II (O)M wherein R7 and m are as defined above, and n is an a:integer of from 1 to 4, with a compound having the formula, R1 wherein each of RI and R21 v~thich may be the same or different, is Cl-C6 alkyl, C 1 -C6 alkoxy, halo Cl-Cs alkoxy or halogen; W is halogen or 130 (0),C wherein R' is C 1 alkyol, benzyl or benzyl substituted with at least one memnber' selected from the group consisting of 0 1 -C 6 al'kyl, C,-C 6 alkoxy, halogen or nitro; and-e is an intege7 of 0, 1 or 2. 17. A method for producing a pyrimkidine derivative as defined in Claim 1 which comprises the steps of Mi reacting a carboxylic acid derivative having the formula, 0 y3 cUR Y.2 20 y t wherein X is oxygen or sulfur; Z is nitrogen Cy 4 each ot Y 2 and y 3 which may be the same or different, is hydrogetr halogen, C,-C 6 alkyl or IC alkoxy; *Y 4is hydrogen, hydroxyl, mercapto, nitro, halogen, C.-0 6 alkyl, 0 2 alkenyl, C 2 -C 6 alkynyl, CQ-CG alkoxy, C3-C, alkenyloxy, C 3 -C6 alkynyloxy, halo C 1 C. alkyl, halo C 2 -C 6 alkenyl, halo C 2 alkynyl, halo C,-C. alkoxy, halo C 3 -C 6 alkenyloxy, halo C3 alkynyloxy, Cl-Cs alkoxy Cl-C 6 alkyl, C 3 -C6 alkenyloxy Cl-C6 alkyl, C 3 -C 6 alkynyloxy Cl-C6 alkyl, cyano, formyl, carboxyl, C 1 -C 6 alkcoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C6 alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of Cl-C6 alkyl, C 1 -C 6 alkoxy, halo Cl-C 6 alkyl, Cl-Cs alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected from the group consisting of Cj-CG alkyl, Cl-C6 alkoxy, halo Cl-C6 alky1, Cl-C 6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected f rom the group consistipig of C 1 -C 5 3 alkyl, Cl-C6 alkoxy, halo Cl-C 6 alkyl, Cl-C6 alkoxycarbonyl and halogen, benzyloxy, benzyloxy subs~ituted with at least one member selected from the group consisting of Cl-C6 :alkyl, CI.-C6 alkoxy, halo Cl-C6 alkyl, Cl-C6 alkoxy- 0006carbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group 16~ '.consisting of Cj-Ct,. ';Alkyl, C 1 -C 6 alkoxy, halo C 1 '-C6 alkyl, Cl-C6 alkoxycarbonyl and halogen, R6 C 3 -C6 alkynyl, 0 C N~R6 wherein R5 and R 6 are as defined above, S R 7 (O)m wherein R7 is Cl-C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl and m is an integer of' 0, 1 or 2, 0 9** 0 -X1 -R 1) wherein X1 is oxygen or sulfur, and R 7 is as defined 00 above, or 541 CH 2 -)jj S R7 integer of from 1 to 4; and each of RI and 'R 2 which may be the same or different, is Cj-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkoxy or halogen, with an acid-halogenating agent or an active esterifying agent to obtain a reaction product; and 133 (ii) reacting the reaction product with an alcohol derivative having the formula, HO-A wherein A is cycloalkyl C 1 alkyl, C 3 cycloalkyl C 1 -C 6 alkyl substituted with at least one member selected from the group consisting of CI-C, alkyl and halogen, C 3 -C, oxacycloalkyl, C 3 oxacycloalkyl substituted with at least one member selected from the group consisting of C 1 C alkyl and halogen, C 3 -C 6 oxacycloalkyl C,-C 6 alkyl, C 3 C, oxacycloalkyl C,-C 6 alkyl substituted with at least one member selected from the group consisting of C,-C 6 alkyl and halogen, C 3 -C s dioxacycloalkyl, C 3 -C s dioxacycloalkyl substituted with at least one member selected from the group consisting of C,-C 6 alkyl and halogen C 3 -C s dioxacycloalkyl C1-C, alkyl or C 3 -C s dioxacycloalkyl C 1 -C 6 alkyl substituted with at least one member selected from *the group consisting of CI-C, alkyl and halogen. 20 18. A method for producing a pyrimidine derivative as defined in Claim 1 which comprises reacting an unesterified pyrimidine derivative having the formula, S S e Y3 11 -z RiVZ wherein each of R1 and R 2 which may be the same or different, is Cl-C 6 alkyl, C 1 -C 6 alkoxy, halo Cl-C 6 alkoxy or halogen; X is oxygen or sulfur; *00Z is nitrogen or Cy4; each of Y1, y2 and y3, which may be the same or diifferent, is hydrogen, halogen, Cl-C 6 alkyl or Cl-C 6 alkoxy; and y4 is hydrogen, hydroxyl, mercapto, nitro, halogen, Cl-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, halo Ci-C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C6 alkynyl, halo Cl-C 6 0 alkoxy, halo C 3 -C 6 alkenyloxy, halo C 3 -C6 alkynyloxy, S Cl-C 6 alkoxy Cl-Cs alkyl, C 3 -C 6 alkenyloxy C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy Cl-Cs alkyl, cyano, formyl, carboxyl, Cl-C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of Cj-C6 alkyl, Cl-Cs alkoxy, halo Cl-Cs alkyl, Cl-Cs alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected from the group consisting Of Cl-C 6 alkyl, Cy-C6 alkoxy, halo C 1 '-C 6 alkyl, CI-C 6 alkoxycarbonyl and halogen, phenylthio, phenylthio, substituted with at least one member selected from the group consisting of Cl-C 6 alkyl, C 1 -C 6 alkoxy, halo Cl-C6 alkyl, Cj-C alkoxycarbonyl and halogen, benzyloxy, benzyloxy substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl, Cj.-C 6 alkoxy, halo CJ.-C6 alkyl, C 1 -C 6 alkoxy- carbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group consisting Of Cl-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C 6 alkyl, C 1 -C 6 alkoxycarbonyl and halogen, R6 sowherein each of R5 and R6, which may be the same or different, is hydrogen, Cl-C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, 0 C C R R6 wherein R5 and R 6 are as defined above, -S R7 11 (0)m 136 wherein R 7 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 C 6 alkynyl and m is an integer of 0, 1 or 2, 0 X-C-R7 wherein X1 is oxygen or sulfur, and R 7 is as defined above, or V' egoe ~C11 2 nii S R 7 so** *00 wherein R 7 and m are as defined above, and n is an integer of from 1 to 4, with a halide having the formula, W 3 -A, wherein A is C 3 -CS cycloalkyl Cj-C 6 alkyl, C 3 -C8 cycloalkyJ. Cl-C 6 alkyl substituted with at least one member selected from the group consisting of Cl-C 6 alkyl and halogen, C 3 C 6 oxacycloalkyl, C 3 -C 6 oxacyclbalkyl substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl and halogen, C 3 -C 6 oxacycloalkyl C 1 -C 6 alkyl, C 3 -C 6 oxacycloalkyl C 1 -C 6 alkyl substituted with at least one member selected from the group consisting of C1-C 6 alkyl 137 and halogen, C 3 dioxacycloalkyl, C3-Cs dioxacycloalkyl substituted with at least one member selected from the group consisting of alkyl and halogen, C 3 -C dioxacycloalkyl CI-C, alkyl or C 3 dioxacycloalkyl C.-C, alkyl substituted with at least one member selected from the group consisting of alkyl and halogen; and W 3 is halogen. 19. A herbicidal composition which comprises as an active ingredient a herbicidally effective amount of a pyrimidine derivative having the formula, 0 1-I z COA 15y2 R1(1 R2 wherein A is C 3 cycloalkyl C,-C 6 alkyl, C 3 cycloalkyl C 1 alkyl substituted with at least one member selected *from the group consisting of CI-C 6 alkyl 9* S S and halogen, C 3 C 6 oxacycloalkyl, C 3 C 6 oxacyc2.oalkyl substituted with at. least one member selected from the group consisting of C 1 C 6 alkyl and halogen, C 3 C 6 oxacycloalkyl. Cl-C 6 alkyl, C 3 -C 6 oxacycloalkyl Cl-C 6 alkyl usbstituted with at least one member selected from the group consisting of C 1 C 6 alkyl and halogen, C 3 'C dioxacycloalkyl, C 3 C 5 dioxacycloalkyl substituted with at least one member selected from the group consisting of C -C 6 alkyl and halogen, C -C 5 dioxacycloalkyl ,C -C aly or 5 dioxacycloalkyl C -C 6 alkyl *1 6 3klo C-C substituted with at least one member slelcted from 0 WO the group consisting of C C 6 alkyl and halogen; each of R 1and R 2, which may be the same or 46600: different, is C I- C 6 alkyl, C I-C 6 alkoxy, halo C1 :.44* alkoxy or halogen; X is oxygen or sulfur; Z is nitrogen or CY 4 each of Y 1 Y 2 and Y 3 which may be the same or different, is hydrogen, halogen, C1- 6 alkyl or C 1 C 6 44 Yis lhydrogen, hydroxyl, mercapto, nitro, halogen, C 1 -C 6 alkyl, C 2 C 6 alkenyl, C 2 C 6 alkynyl, C 1 C 6 alkoxy, C 3 6 alkenyloxy, C 3 C 6 alkynyloxy, halo C1- 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 C 6 alkynyl, halo C 1 C 6 L 4 alkoxy, halo C 3 -C 6 alkenyloxy, halo C 3 -C 6 alkynyloxy, C 1 -C 6 alkoxy Cl-C6 alkyl, C 3 -C 6 alkenyloxy CI-C6 alkyl, C 3 -C 6 alkynyloxy Cl-C 6 alkyl, cyano, formyl, carboxyl, Cj-C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl, CI-C 6 alkoxy, halo Cl-C 6 alkyl, Cl-C 6 alkoxycarbonyl and1 halogeln, phenoxy, phenoxy substituted with at least one member selected from the group consisting of Cj-C 6 alkyl, Cl-C6 alkoxy, halo Cl-C 6 alkyl, C 1 -C 6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected se from the group consisting of Cl-C 6 alkyl, C 1 -C6 alkoxy, halo Cl-C 6 alkyl, Cl-C6 alkoxycarbonyl, and halogen, benzyloxy, benzyloxy substituted with at least one member selected from the group consisting Of Cl-C 6 0a alkyl, Cl-C 6 alkoxy, halo Cl-Cs alkyl, C 1 -C 6 alkoxy- carbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group S b consisting Of Cj.-C 6 alkyl, Cl-C 6 alkoxy, halo Cl-C6 $vto alkyl, Cl-C6 alkoxycarbonyl and halogen, R6 wherein each of R5 and R 6 which may be the same or different, is hydrogen, Cl-C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C6 alkynyl, 140 0 C N R6 wherein R 5 and R 6 are as defined above, S -R7- 1i (0)m wherein R 7 is C 1 alkyl, C 3 -C 6 alkenyl or C3-C alkynyl and m is an integer of 0, 1 or 2, 0 II XI -C R7 wherein X 1 is oxygen or sulfur, and R 7 is as defined above, or -tCH 2 i- R7 (0)m wherein R 7 and m are as defined above, and n is an integer of from 1 to 4; and an inert carrier or a diluent. 20. A method for controlling undesirable weeds, which comprises applying the herbicidal composition of Claim to an area where undesirable weeds grow or are likely to grow. 21. The pyrimidine derivative of Claim 1 when used as a herbicide. DATED THIS 3RD DAY OF FEBRUARY 1993 SUMITOMO CHEMICAL COMPANY, LIMITED By its Patent Attorneys: GRIFFITH HACK CO 484 Fellows Institute of Patent S7? Attorneys of Australia.