Pyrimidine derivatives and herbicides containing them Number:6,806,230 from the United States Patent and Trademark Office (PTO) owispatent Pyrimidine derivatives having excellent herbicidal activities for crop plants and selectivity between crop plants and weeds, are presented. Pyrimidine derivatives represented by the following formula (I): ##STR1##wherein R.sup.1 is a hydrogen atom, an alkyl group, a haloalkyl group or the like; R.sup.2 is an alkyl group, a phenyl group which may be substituted, or the like; R.sup.3 is a hydrogen atom, an alkyl group, an alkynyl group or the like; R.sup.7 is a hydrogen atom, a halogen atom, an alkyl group or the like; R.sup.8 is a hydrogen atom, an alkyl group or the like, W is a --C(.dbd.Q) Z-- group or a --SO.sub.2 -- group; Q is O or S; Z is O, S, a --C(R.sup.4)R.sup.5 --, a --NR.sup.6 group or the like; each of R.sup.4 and R.sup.5 is a hydrogen atom, an alkyl group, an alkoxy group or the like; R.sup.6 is a hydrogen atom or an alkyl group; and Ar is a phenyl group which may be substituted, a pyridyl group which may be substituted, or the like, and herbicides containing such pyrimidine derivatives as active ingredients.<H derivatives, containing, Pyrimidine, deri, 6806230.html, Patent, pto, 6806230

Title: Pyrimidine derivatives and herbicides containing them

Abstract: Pyrimidine derivatives having excellent herbicidal activities for crop plants and selectivity between crop plants and weeds, are presented. Pyrimidine derivatives represented by the following formula (I): ##STR1##wherein R.sup.1 is a hydrogen atom, an alkyl group, a haloalkyl group or the like; R.sup.2 is an alkyl group, a phenyl group which may be substituted, or the like; R.sup.3 is a hydrogen atom, an alkyl group, an alkynyl group or the like; R.sup.7 is a hydrogen atom, a halogen atom, an alkyl group or the like; R.sup.8 is a hydrogen atom, an alkyl group or the like, W is a --C(.dbd.Q) Z-- group or a --SO.sub.2 -- group; Q is O or S; Z is O, S, a --C(R.sup.4)R.sup.5 --, a --NR.sup.6 group or the like; each of R.sup.4 and R.sup.5 is a hydrogen atom, an alkyl group, an alkoxy group or the like; R.sup.6 is a hydrogen atom or an alkyl group; and Ar is a phenyl group which may be substituted, a pyridyl group which may be substituted, or the like, and herbicides containing such pyrimidine derivatives as active ingredients.

Patent Number: 6,806,230 Issued on 10/19/2004 to Yasuda, et al.

Inventors: Yasuda; Atsushi (Chiba, JP); Takabe; Fumiaki (Shizuoka, JP); Urushibata; Ikumi (Chiba, JP); Yamaguchi; Mikio (Shizuoka, JP); Yamaji; Yoshihiro (Shizuoka, JP); Fujinami; Makoto (Shizuoka, JP); Miyazawa; Takeshige (Shizuoka, JP)
Assignee: Kumiai Chemical Industry Co., Ltd. (Tokyo, JP)
Ihara Chemical Industry Co., Ltd. (Tokyo, JP)

Appl. No.: 10/070,804

Filed: March 11, 2002

PCT Filed: September 08, 2000

PCT No.: PCT/JP00/06165

PCT Pub. No.: WO01/17975

PCT Pub. Date: March 15, 2001

Foreign Application Priority Data


Sep 09, 1999 [JP]			11-255029

Current U.S. Class: 504/239 ; 504/225; 514/256; 514/269; 514/274; 544/297; 544/298; 544/315

Field of Search: 514/269,274,256 544/297,298,315 504/239,225

Foreign Patent Documents


764641	Mar., 1997	EP
96/22980	Aug., 1996	WO

Other References

Bargar, T. M. et. al., Pesticide Sciences, 1999, vol. 55, No. 11, pp. 1059-1069.* .
T. M. Bargar, et al., Pesticide Science, vol. 55, pp. 1059-1069, XP-002154128, "A Comparative Molecular Field Analysis Study of Obtusifoliol 14.alpha.-Methyl Demethylase Inhibitos", 1999. .
Patent Abstracts of Japan, JP 42-012906, Jul. 24, 1967. .
A. G. Beaman, et al., Database CA 'Online! Chemical Abstracts Service, AN 1969:422065, XP-002208032, "Studies in the Nitroimidazole Series. III. 2-Nitroimidazole Derivatives Substituted in the 1-Position", 1968. .
P. R. Bovy, et al., Database CA 'Online! Chemical Abstracts Service, AN 1994-299228, XP-002208033, "Synthesis of Heterocyclic.Beta.Amino Acids. A Convenient Preparation of Beta.-Amino-5-Pyrimidinepropanoic Acid and Derivatives", 1993. .
A. Takamizawa et al.: "Studies on pyrimidine derivaties and rerated compounds LXXVII" Chemical & Pharmaceutical Bulletin, vol. 21, No. 4, pp. 770-784 1983..

Primary Examiner: Raymond; Richard L.
Assistant Examiner: Truong; Tamthom N.
Attorney, Agent or Firm: Oblon, Spivak, McClelland, Maier & Neustadt, P.C.

Claims

What is claimed is:

1. A pyrimidine derivative represented by the formula (I) ##STR58## wherein R.sup.1 is a hydrogen atom (except for a case where R.sup.2 hydrogen atom, and W.dbd.SO.sub.2), a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylcarbonyl C.sub.1 -C.sub.6 alkyl group, a hydroxyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, a cyano group, a cyano C.sub.1 -C.sub.6 alkyl group, a nitro group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group), a C.sub.1 -C.sub.6 alkylthio group (except for a case where R.sup.2 =phenyl group, and W.dbd.SO.sub.2), a C.sub.2 -C.sub.6 alkenylthio group, a C.sub.2 -C.sub.6 alkynylthio group, a C.sub.3 -C.sub.6 cycloalkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.3 -C.sub.6 cycloalkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.3 -C.sub.6 cycloalkylsulfonyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.2 -C.sub.6 alkenyl group, a carboxyl group, a carboxyl C.sub.1 -C.sub.6 alkyl group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a dioxolanyl group (this group may be substituted by a C.sub.1 -C.sub.6 alkyl group), an aldehyde group, an oxiranyl group, a NR.sup.9 R.sup.10 group or a CONR.sup.9 R.sup.10 group, and R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group, and R.sup.10 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group or a benzyloxycarbonyl group; R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.2 -C.sub.7 acyl group, a cyano group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a CR.sup.11 R.sup.12 NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a CR.sup.11 R.sup.12 CONR.sup.9 R.sup.10 group or a group represented by the formulae R.sup.2 -1 or R.sup.2 -2: ##STR59## and wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, and n is an integer of from 1 to 3, and when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group; each of R.sup.11 and R.sup.12 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group or a C.sub.1 -C.sub.6 alkoxy group; R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a di C.sub.1 -C.sub.6 alkylamino group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.6 alkyl group, an oxiranyl C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group; W is a --C(.dbd.Q)Z-- group or a --SO.sub.2 -- group, Q is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, a --NR.sup.6 -- group, a --CH.sub.2 CH.sub.2 -- group, a --CH.dbd.CH-- group, a --C(R.sup.4)R.sup.5 -- group, a --C(R.sup.4)R.sup.5 --Q-- group, a --Q--C(R.sup.4)R.sup.5 -- group, a --C(.dbd.Q)-- group, a --NR.sup.6 NR.sup.6a -- group or a --NR.sup.6 C(R.sup.4)R.sup.5 -- group, and each of R.sup.4 and R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a halogen atom, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.6 alkylthio group, each of R.sup.6 and R.sup.6a is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group; Ar is a group represented by the formulae Ar-1 or Ar-2: ##STR60##

and wherein X' is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n' is an integer of from 1 to 3, and when n' is an integer of 2 or 3, the plurality of X' may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group; R.sup.7 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, (except for a case where R.sup.1 is a hydrogen atom and R.sup.2 is a phenyl group and W is SO.sub.2), a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group; and R.sup.8 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group.

2. A pyrimidine derivative represented by the formula ##STR61## wherein R.sup.1 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylcarbonyl C.sub.1 -C.sub.6 alkyl group, a hydroxyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, a cyano group, a nitro group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group), a C.sub.1 -C.sub.6 alkylthio group, a C.sub.2 -C.sub.6 alkenylthio group, a C.sub.2 -C.sub.6 atkynylthio group, a C.sub.3 -C.sub.6 cycloalkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.3 -C.sub.6 cycloalkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.3 -C.sub.6 cycloalkylsulfonyl group, a hydroxyalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.2 -C.sub.6 alkenyl group, a carboxyl group, a carboxyl C.sub.1 -C.sub.6 alkyl group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a dioxolanyl group (this group may be substituted by a C.sub.1 -C.sub.6 alkyl group), an aldehyde group, an oxiranyl group, a NR.sup.9 R.sup.10 group or a CONR.sup.9 R.sup.10 group, and R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group, and R.sup.10 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group or a benzyloxycarbonyl group; R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.2 -C.sub.7 acyl group, a cyano group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a CR.sup.11 R.sup.12 NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a CR.sup.11 R.sup.12 CONR.sup.9 R.sup.10 group or a group represented by the formulae R.sup.2 -1 or R.sup.2 -2: ##STR62## and wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n is an integer of from 1 to 3, and when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group, and each of R.sup.11 and R.sup.12 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group or a C.sub.1 -C.sub.6 alkoxy group; R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a di C.sub.1 -C.sub.6 alkylamino group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.6 alkyl group, an oxiranyl C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group; W is a --C(.dbd.Q)Z-- group, Q is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, a --NR.sup.6 -- group, a --CH.sub.2 CH.sub.2 -- group, a --CH.dbd.CH-- group, a --C(R.sup.4)R.sup.5 -- group, a --C(R.sup.4)R.sup.5 --Q-- group, a --Q--C(R.sup.4)R.sup.5 -- group, a --C(.dbd.Q)-- group, a --NR.sup.6 NR.sup.6a group or a --NR.sup.6 C(R.sup.4)R.sup.5 -- group, each of R.sup.4 and R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a halogen atom, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.6 alkylthio group, each of R.sup.6 and R.sup.6a is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group; Ar is a group represented by the formulae Ar to Ar-1 or Ar-2: ##STR63##

and wherein X' is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n' is an integer of from 1 to 3, and when n' is an integer of 2 or 3, the plurality of X' may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group); R.sup.7 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group; and R.sup.8 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group.

3. A pyrimidine derivative represented by the formula ##STR64## wherein R.sup.1 is a halogen atom, a C.sub.1 -C.sub.6 alkyl group, an oxo C.sub.1 -C.sub.6 alkyl group, a hydroxyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, a cyano group, a nitro group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group), a C.sub.2 -C.sub.6 alkenylthio group, a C.sub.2 -C.sub.6 alkynylthio group, a C.sub.3 -C.sub.6 cycloalkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.3 -C.sub.6 cycloalkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.3 -C.sub.6 cycloalkylsulfonyl group, a hydroxyalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.2 -C.sub.6 alkenyl group, a carboxyl group, a carboxyl C.sub.1 -C.sub.6 alkyl group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a dioxolanyl group (this group may be substituted by a C.sub.1 -C.sub.6 alkyl group), an aldehyde group, an oxiranyl group, a NR.sup.9 R.sup.10 group or a CONR.sup.9 R.sup.10 group, and R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group, and R.sup.10 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group or a benzyloxycarbonyl group; R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.2 -C.sub.7 acyl group, a cyano group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a CR.sup.11 R.sup.12 NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a CR.sup.11 R.sup.12 CONR.sup.9 R.sup.10 group or a group represented by the formulae R.sup.2 -1 or R.sup.2 -2: ##STR65## and (wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n is an integer of from 1 to 3, and when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group), and each of R.sup.11 and R.sup.12 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group or a C.sub.1 -C.sub.6 alkoxy group; R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a di C.sub.1 -C.sub.6 alkylamino group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.6 alkyl group, an oxiranyl C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group; W is a --SO.sub.2 -- group; Ar is a group represented by the formulae Ar-1 or Ar-2: ##STR66##

and wherein X' is a hydrogen atom, a halogen atom, an alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n' is an integer of from 1 to 3, and when n' is an integer of 2 or 3, the plurality of X' may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group; R.sup.7 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group; and R.sup.8 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group.

4. A pyrimidine derivative represented by the formula ##STR67##

wherein R.sup.1 is a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylcarbonyl C.sub.1 -C.sub.6 alkyl group, a hydroxyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, a cyano group, a nitro group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group), a C.sub.1 -C.sub.6 alkylthio group (except for a case where R.sup.2 =phenyl group, and W.dbd.SO.sub.2), a C.sub.2 -C.sub.6 alkenylthio group, a C.sub.2 -C.sub.6 alkynylthio group, a C.sub.3 -C.sub.6 cycloalkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.3 -C.sub.6 cycloalkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.3 -C.sub.6 cycloalkylsulfonyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.2 -C.sub.6 alkenyl group, a carboxyl group, a carboxyl C.sub.1 -C.sub.6 alkyl group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a dioxolanyl group (this group may be substituted by a C.sub.1 -C.sub.6 alkyl group), an aldehyde group, an oxiranyl group, a NR.sup.9 R.sup.10 group or a CONR.sup.9 R.sup.10 group, and R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group, and R.sup.10 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group or a benzyloxycarbonyl group; R.sup.2 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.2 -C.sub.7 acyl group, a cyano group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a CR.sup.11 R.sup.12 NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a CR.sup.11 R.sup.12 CONR.sup.9 R.sup.10 group or a group represented by the formulae R.sup.2 -1 or R.sup.2 -2: ##STR68##

and wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n is an integer of from 1 to 3, and when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group, and each of R.sup.11 and R.sup.12 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group or a C.sub.1 -C.sub.6 alkoxy group; R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a di C.sub.1 -C.sub.6 alkylamino group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano C.sub.1 -C.sub.6 alkyl group or a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.6 alkyl group; W is a --C(.dbd.Q)Z-- group or a --SO.sub.2 -- group, Q is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, a --NR.sup.6 -- group, a --C(R)R.sup.5 -- group, a --C(R.sup.4)R.sup.5 --Q-- group, a --NR.sup.6 NR.sup.6 -- group or a --NR.sup.6 C(R.sup.4)R.sup.5 -- group, and each of R.sup.4 and R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a halogen atom or a C.sub.1 -C.sub.6 alkoxy group, and each of R.sup.6 and R.sup.6a is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group; Ar is a group represented by any one of the formulae Ar-1 or Ar-2: ##STR69## and wherein X' is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n' is an integer of from 1 to 3, and when n' is an integer of 2 or 3, the plurality of X' may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group; R.sup.7 is a hydrogen atom or a halogen atom; and R.sup.8 is a hydrogen atom.

5. A pyrimidine derivative represented by the formula ##STR70## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylcarbonyl C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a phenyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, a cyano group, a nitro group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group), a C.sub.1 -C.sub.6 alkylthio group (except for a case where R.sup.2 =phenyl group, and W.dbd.SO.sub.2), a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.2 -C.sub.6 alkenyl group, a carboxyl group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group; R.sup.2 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group) a C.sub.2 -C.sub.7 acyl group, or a group represented by the formula R.sup.2 -1: ##STR71## and wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n is an integer of from 1 to 3, and when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group, and R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group, and R.sup.10 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group or a benzyloxycarbonyl group, and each of R.sup.11 and R.sup.12 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group or a C.sub.1 -C.sub.6 alkoxy group; R.sup.3 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group or a cyano C.sub.1 -C.sub.6 alkyl group; W is a --C(.dbd.Q)Z-- group or a --SO.sub.2 -- group, Q is an oxygen atom or a sulfur atom, Z is a --NR.sup.6 -- group, a --C(R.sup.4)R.sup.5 -- group, a --C(R.sup.4)R.sup.5 --Q-- group, a --NRR.sup.6a -- group or a --NR.sup.6 C(R.sup.4)R.sup.5 -- group, and each of R.sup.4 and R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a halogen atom or a C.sub.1 -C.sub.6 alkoxy group, and each of R.sup.6 and R.sup.6a is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group; Ar is a group represented by formula Ar-1, ##STR72## and wherein X' is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n' is an integer of from 1 to 3, and when n' is an integer of 2 or 3, the plurality of X' may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group; R.sup.7 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group, and R.sup.8 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group.

6. A herbicide containing the pyrimidine derivative as defined in claim 1, as an active ingredient.

7. A herbicide containing the pyrimidine derivative as defined in claim 2, as an active ingredient.

8. A herbicide containing the pyrimidine derivative as defined in claim 3, as an active ingredient.

9. A herbicide containing the pyrimidine derivative as defined in claim 4, as an active ingredient.

10. A herbicide containing the pyrimidine derivative as defined in claim 5, as an active ingredient.

Description

TECHNICAL FIELD

The present invention relates to novel pyrimidine derivatives and herbicides containing them as active ingredients.

BACKGROUND ART

Pyrimidine derivatives are known, for example, by the specification of international application WO95/12582, the specification of international application WO96/22980 and the specification of international application WO97/12877. However, the pyrimidine derivatives of the present invention have not been known.

A herbicide to be used for crop plants is desired to be a chemical which exhibits a sufficient herbicidal effect at a low dose and yet provides selectivity between crop plants and weeds, when applied to an upland field or to a paddy field. Accordingly, it is an object of the present invention to provide a compound which has an excellent herbicidal activity and selectivity between crop plants and weeds.

DISCLOSURE OF THE INVENTION

Under these circumstances, the present inventors have synthesized various substituted pyrimidine derivatives and have studied their physiological activities. As a result, it has been found that novel substituted pyrimidine derivatives as the compounds of the present invention have excellent herbicidal activities and selectivity between crop plants and weeds, and the present invention has been accomplished. Namely, the present invention provides a pyrimidine derivative represented by the formula (I) ##STR2##

wherein R.sup.1 is a hydrogen atom (except for a case where R.sup.2 =hydrogen atom, and W.dbd.SO.sub.2), a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylcarbonyl C.sub.1 -C.sub.6 alkyl group, a hydroxyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, a cyano group, a cyano C.sub.1 -C.sub.6 alkyl group, a nitro group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group), a C.sub.1 -C.sub.6 alkylthio group (except for a case where R.sup.2 =phenyl group, and W.dbd.SO.sub.2), a C.sub.2 -C.sub.6 alkenylthio group, a C.sub.2 -C.sub.6 alkynylthio group, a C.sub.3 -C.sub.6 cycloalkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.3 -C.sub.6 cycloalkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.3 -C.sub.6 cycloalkylsulfonyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.2 -C.sub.6 alkenyl group, a carboxyl group, a carboxyl C.sub.1 -C.sub.6 alkyl group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a dioxolanyl group (this group may be substituted by a C.sub.1 -C.sub.6 alkyl group), an aldehyde group, an oxiranyl group, a NR.sup.9 R.sup.10 group or a CONR.sup.9 R.sup.10 group, R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group or a C.sub.1 -C.sub.6 alkylsulfonyl group, R.sup.10 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group or a benzyloxycarbonyl group, here R.sup.9 and R.sup.10 may, together with the carbon atom to which they are bonded, form a 5- to 7-membered saturated ring, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group (this group may be substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.4 haloalkyl group), a C.sub.2 -C.sub.7 acyl group, a cyano group, a di C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group, a hydroxyimino C.sub.1 -C.sub.6 alkyl group, a dioxolanyl group (this group may be substituted by a C.sub.1 -C.sub.6 alkyl group), a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 hydroxyalkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, a CR.sup.11 R.sup.12 NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a CR.sup.11 R.sup.12 CONR.sup.9 R.sup.10 group or a group represented by any one of the formulae R.sup.2 -1 to R.sup.2 -13: ##STR3##

(wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a s C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n is an integer of from 1 to 3, when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group), each of R.sup.11 and R.sup.12 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group or a C.sub.1 -C.sub.6 alkoxy group, R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a di C.sub.1 -C.sub.6 alkylamino group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a cyano C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.6 alkyl group, an oxiranyl C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group, W is a --C(.dbd.Q)Z-- group or a --SO.sub.2 -- group, Q is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, a --NR.sup.6 -- group, a --CH.sub.2 CH.sub.2 -- group, a --CH.dbd.CH-- group, a --C(R.sup.4)R.sup.5 -- group, a --C(R.sup.4)R.sup.5 --Q-- group, a --Q--C(R.sup.4)R.sup.5 -- group, a --C(.dbd.Q)-- group, a --NR.sup.6 NR.sup.6a -- group or a --NR.sup.6 C(R.sup.4)R.sup.5 -- group, each of R.sup.4 and R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a halogen atom, a C.sub.1 -C.sub.6 alkoxy group or a C.sub.1 -C.sub.6 alkylthio group, each of R.sup.6 and R.sup.6a is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group or a C.sub.2 -C.sub.6 alkynyl group, here R.sup.3 and R.sup.6 may, together with the carbon atom to which they are bonded, form a 5- to 7-membered cyclic urea, Ar is a group represented by any one of the formulae Ar-1 to Ar-17: ##STR4## ##STR5##

(wherein X' is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group, a NR.sup.9 R.sup.10 group, a CONR.sup.9 R.sup.10 group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkyloxy group, a C.sub.2 -C.sub.7 acyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylsulfinyl group, a C.sub.1 -C.sub.6 alkylsufonyl group, a cyano group, a nitro group or a C.sub.1 -C.sub.4 haloalkyl group, n' is an integer of from 1 to 3, m is an integer of from 0 to 3, when n' is an integer of 2 or 3, the plurality of X' may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C.sub.1 -C.sub.3 alkylenedioxy group), R.sup.7 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group, and R.sup.8 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group; and a herbicide containing it as an active ingredient.

Now, definitions of terms used in this specification will be shown below.

The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The C.sub.1 -C.sub.6 alkyl group means a straight chain or branched chain alkyl group having a carbon number of from 1 to 6, unless otherwise specified, and it may, for example, be a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group.

The C.sub.3 -C.sub.6 cycloalkyl group represents a cycloalkyl group having a carbon number of from 3 to 6, and it may, for example, be a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.

The C.sub.2 -C.sub.6 alkenyl group represents a straight chain or branched chain alkenyl group having a carbon number of from 2 to 6, and it may, for example, be an ethenyl group or a 2-propenyl group.

The C.sub.2 -C.sub.6 alkynyl group represents a straight chain or branched chain alkynyl group having a carbon number of from 2 to 6, and it may, for example, be an ethynyl group or a 2-propynyl group.

The C.sub.1 -C.sub.4 haloalkyl group represents a straight chain or branched chain alkyl group having a carbon number of from 1 to 4, which is substituted by from 1 to 9 same or different halogen atoms, unless otherwise specified, and it may, for example, be a chloromethyl group, a trifluoromethyl group or a tetrafluoroethyl group.

The C.sub.1 -C.sub.6 alkoxy group represents an (alkyl)-O-group wherein the alkyl moiety has the above meaning, and it may, for example, be a methoxy group, an ethoxy group or a propoxy group.

The C.sub.2 -C.sub.6 alkenyloxy group represents an (alkenyl)-O-group wherein the alkenyl moiety has the above meaning, and it may, for example, be an ethenyloxy group or a 2-propenyloxy group.

The C.sub.2 -C.sub.6 alkynyloxy group represents an (alkynyl)-O-group wherein the alkynyl moiety has the above meaning, and it may, for example, be an ethynyloxy group or a 2-propynyloxy group.

The C.sub.3 -C.sub.6 cycloalkyloxy group represents a (cycloalkyl)-O-group wherein the cycloalkyl moiety has the above meaning, and it may, for example, be a cyclopropyloxy group, a cyclopentyloxy group or a cyclohexyloxy group.

The C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group represents an (alkyl)-O-(alkylene)-group, wherein the alkyl moiety has the above meaning, and it may, for example, be a methoxymethyl group or an ethoxymethyl group.

The C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.6 alkyl group represents a (cycloalkyl)-(C.sub.1 -C.sub.6 alkylene) group wherein the cycloalkyl moiety has the above meaning, and it may, for example, be a cyclopropylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group or a cyclohexylethyl group.

The C.sub.1 -C.sub.4 haloalkoxy group represents a (haloalkyl)-O-group wherein the haloalkyl moiety has the above meaning, and it may, for example, be a trifluoromethoxy group or a 2,2,2-trifluoroethoxy group.

The C.sub.1 -C.sub.6 alkylthio group, the C.sub.1 -C.sub.6 alkylsulfinyl group and the C.sub.1 -C.sub.6 alkylsulfonyl group, represent an (alkyl)-S-group, an (alkyl)-SO-group and an (alkyl)-SO.sub.2 -group, wherein the alkyl moiety has the above meaning, and they may, for example, be a methylthio group, an ethylthio group, a methylsultinyl group, an ethylsulfinyl group, a methylsulfonyl group or an ethylsulfonyl group.

The C.sub.2 -C.sub.6 alkenylthio group, the C.sub.2 -C.sub.6 alkenylsulfinyl group and the C.sub.2 -C.sub.6 alkenylsulfonyl group, represent an (alkenyl)-S-group, an (alkenyl)-SO-group and an (alkenyl)-SO.sub.2 -group, wherein the alkenyl moiety has the above meaning, and they may, for example, be a propenylthio group, a butenylthio group, a propenylsulfinyl group, a butenylsulfinyl group, a propenylsulfonyl group or a butenylsulfonyl group.

The C.sub.2 -C.sub.6 alkynylthio group, the C.sub.2 -C.sub.6 alkynylsulfinyl group and the C.sub.2 -C.sub.6 alkynylsulfonyl group, represent an (alkynyl)-S-group, an (alkynyl)-SO-group and an (alkynyl)-SO.sub.2 -group, wherein the alkynyl moiety has the above meaning, and they may, for example, be an ethynylthio group, a 2-propynylthio group, an ethynylsulfinyl group, a 2-propynylsulfinyl group, an ethynylsulfonyl group or a 2-propynylsulfonyl group.

The C.sub.3 -C.sub.6 cycloalkylthio group, the C.sub.3 -C.sub.6 cycloalkylsulfinyl group and the C.sub.3 -C.sub.6 cycloalkylsulfonyl group, represent a (cycloalkyl)-S-group, a (cycloalkyl)-SO-group, and a (cycloalkyl)-SO.sub.2 -group, wherein the cycloalkyl moiety has the above meaning, and they may, for example, be a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, a cyclopropylsulfinyl group, a cyclobutylsulfinyl group, a cyclopentylsulfinyl group, a cyclohexylsulfinyl group, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group or a cyclohexylsulfonyl group.

The C.sub.1 -C.sub.6 alkylthio C.sub.1 -C.sub.6 alkyl group represents an (alkyl)-S-(alkylene) group wherein the alkyl moiety has the above meaning, and it may, for example, be a methylthiomethyl group, an ethylthiomethyl group, a propylthiomethyl group or a methylthioethyl group.

The C.sub.2 -C.sub.7 acyl group represents a C.sub.1 -C.sub.6 alkylcarbonyl group, a C.sub.2 -C.sub.6 alkenylcarbonyl group, a C.sub.2 -C.sub.6 alkynylcarbonyl group, a C.sub.3 -C.sub.6 cycloalkylcarbonyl group or a benzoyl group, and it may, for example, be an acetyl group, a propionyl group, a n-butyryl group, an isobutyryl group, a cyclopropylcarbonyl group or a benzoyl group.

The C.sub.1 -C.sub.6 alkylcarbonyl C.sub.1 -C.sub.6 alkyl group may, for example, be a methylcarbonylmethyl group, an ethylcarbonylmethyl group or a propylcarbonylmethyl group.

The diC.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group may, for example, be a dimethoxymethyl group or a diethoxymethyl group.

The C.sub.1 -C.sub.6 alkoxyimino C.sub.1 -C.sub.6 alkyl group may, for example, be a methoxyiminomethyl group or an ethoxyiminomethyl group.

The hydroxyimino C.sub.1 -C.sub.6 alkyl group may, for example, be a hydroxyiminomethyl group or a hydroxyiminoethyl group.

The cyano C.sub.1 -C.sub.6 alkyl group may, for example, be a cyanomethyl group or a cyanoethyl group.

The C.sub.1 -C.sub.6 hydroxyalkyl group may, for example, be a hydroxymethyl group or a hydroxyethyl group.

The C.sub.1 -C.sub.6 alkoxycarbonyl group may, for example, be a methoxycarbonyl group or an ethoxycarbonyl group.

The C.sub.1 -C.sub.6 alkoxycarbonyl C.sub.1 -C.sub.6 alkyl group may, for example, be a methoxycarbonyl methyl group or an ethoxycarbonyl methyl group.

The carboxyl C.sub.1 -C.sub.6 alkyl group may, for example, be a carboxymethyl group or a carboxyethyl group.

The diC.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl group may, for example, be a diethoxymethyl group or a 2-dimethoxyethyl group.

The diC.sub.1 -C.sub.6 alkylamino group is a dialkylamino group wherein the alkylalkyl moiety has the above meaning, and it may, for example, be a dimethylamino group or a diethylamino group.

BEST MODE FOR CARRYING OUT THE INVENTION

Now, typical specific examples of the compound of the present invention represented by the formula (I) will be exemplified in Tables 1 to 39. However, the compound of the present invention is not limited to such compounds. The compound numbers will be referred to in the subsequent description. Further, in a case where the compound of the present invention or the disclosed compound has at least one asymmetric carbon, its all steric isomers are included in the compound of the present invention.

In the tables in this specification, S-isomer and R-isomer represent S-isomer and R-isomer of optical isomers, respectively, and in a case where there is no specific representation even when the compound has an asymmetric carbon, such represents a racemate. Further, in the tables, A-isomer and B-isomer represent diastereomers such that when resolved by silica gel column chromatography, one eluting first is designated as A-isomer, and one eluting later is designated as B-isomer. In a case where there is no representation even if diastereomers exist, such represents a mixture of diastereomers.

The following representations in the tables in this specification represent the respective corresponding groups as shown below.

Me: methyl group Et: ethyl group Pr: n-propyl group Pr-i: isopropyl group Pr-c: cyclopropyl group Bu: n-butyl group Bu-i: isobutyl group Bu-s: sec-butyl group Bu-t: tert-butyl group Bu-c: cyclobutyl group Pen: n-pentyl group Pen-i: isopentyl group Pen-c: cyclopentyl group Hex-c: cyclohexyl group

TABLE 1 ##STR6## m. p. (.degree. C.) or refractive Compound index No. R.sup.1 R.sup.2 R.sup.3 Z Xn Q Diastereomer (n.sub.D.sup.20) 1-1 CClF.sub.2 Pr-c H CH.sub.2 H O 124-127 1-2 CClF.sub.2 Pr-c H CH.sub.2 4-OMe O 116-119 1-3 CClF.sub.2 Pr-c H CH.sub.2 4-Cl O 125-128 1-4 CClF.sub.2 Pr-c H CH.sub.2 4-CF.sub.3 O 111-114 1-5 CF.sub.3 Pr-i H CH.sub.2 H O 144-146 1-6 CF.sub.3 Pr-i H CH.sub.2 4-OMe O 114-117 1-7 CF.sub.3 Pr-i H CH(Me) H O 1.5163 1-8 CF.sub.3 Pr-i Me CH.sub.2 H O 106-109 1-9 CF.sub.3 Pr-i Me CH.sub.2 4-OMe O 1.5289 1-10 CF.sub.3 Pr-i Me S H O 131-133 1-11 CF.sub.3 Pr-i Me S 4-OMe O 156-159 1-12 CF.sub.3 Pr-i Me CH.sub.2 4-F O 109-110 1-13 CF.sub.3 Pr-i Me CH.sub.2 4-OEt O 1.5151 1-14 CF.sub.3 Pr-i Me S 4-Cl O 1-15 CClF.sub.2 Pr-i Me CH.sub.2 H O 109-112 1-16 CClF.sub.2 Pr-i Me CH.sub.2 4-OMe O Not Measurable 1-17 CClF.sub.2 Pr-i Me S H O 127-130 1-18 CClF.sub.2 Pr-i Me S 4-OMe O 136-139 1-19 CClF.sub.2 Pr-i Me O H O 115-118 1-20 CF.sub.3 Pr-i Me CH.sub.2 2-Cl O 178-181 1-21 CF.sub.3 Pr-i Me CH.sub.2 3-Cl O 122-125 1-22 CF.sub.3 Pr-i Me CH.sub.2 4-Cl O 99-101 1-23 CF.sub.3 Pr-i Me CH.sub.2 4-Me O 76-79 1-24 CF.sub.3 Pr-i Mo CH.sub.2 4-CF.sub.3 O 105-108 1-25 CClF.sub.2 Pr-i Me CH.sub.2 4-F O 126-129 1-26 CF.sub.3 Pr-i Et CH.sub.2 H O 87-90 1-27 CF.sub.3 Pr-i Et CH.sub.2 4-F O 130-132 1-25 CF.sub.3 Pr-i Me NH H O 149-150 1-29 CF.sub.3 Pr-i Me NH 4-Cl O

TABLE 2 Dia- m.p. (.degree. C.) Compound stereo- or refractive No. R.sup.1 R.sup.2 R.sup.3 Z Xn Q mer index (n.sub.D.sup.20) 1-30 CF.sub.3 Me Me CH.sub.2 H O 1.5258 1-31 CF.sub.3 Me Me CH.sub.2 4-F O 1.5202 1-32 CF.sub.3 Et Me CH.sub.2 H O 40-41 1-33 CF.sub.3 Et Me CH.sub.2 4-F O 72-73 1-34 CF.sub.3 Pr-c Me CH.sub.2 H O Not Measurable 1-35 CF.sub.3 Pr-c Me CH.sub.2 4-F O 97-99 1-36 CF.sub.3 Ph Me CH.sub.2 4-F O 93-94 1-37 CClF.sub.2 Pr-i Me NH 4-Me O 135-137 1-38 CClF.sub.2 Pr-i Me NH H O 146-147 1-39 CF.sub.3 Pr-i Me CH.sub.2 3-CF.sub.3 O 119-120 1-40 CF.sub.3 Pr-i Me CH.sub.2 2,5-F.sub.2 O 145-146 1-41 CF.sub.3 Pr-i Me CH.sub.2 4-Br O 93-95 1-42 CF.sub.3 Pr-i Me CH.sub.2 4-I O 102-104 1-43 CF.sub.3 Pr-i Me CH.sub.2 4-Bu-t O 101-102 1-44 CF.sub.3 Pr-i Me CH.sub.2 4-SMe O 69-71 1-45 CF.sub.3 Pr-i Me CH.sub.2 3,4-Cl.sub.2 O 145-146 1-46 CF.sub.3 Pr-i Me CH.sub.2 2-F,4-Cl O 115-116 1-47 CF.sub.3 Pr-i Me CH.sub.2 3-OMe,4-Cl O 129-131 1-48 CF.sub.3 Pr-i Et CH.sub.2 4-Cl O 120-123 1-49 CF.sub.3 Pr-i Pr CH.sub.2 4-Cl O 140-141 1-50 CF.sub.3 Pr-i Me CH.sub.2 2-Me O 154-155 1-51 CF.sub.3 Pr-i Me CH.sub.2 3-Me O 93-94 1-52 CF.sub.3 Pr-i Me CH.sub.2 4-NO.sub.3 O 146-149 1-53 CF.sub.3 Bu-t Me CH.sub.2 4-F O 91-92 1-54 CF.sub.3 Bu-t Me CH.sub.2 4-Cl O 111-112 1-55 CF.sub.3 Bu-t Me CH.sub.2 4-Me O 84-87 1-56 CH.sub.3 Pr-i Me CH.sub.2 4-Cl O 118-119 1-57 CF.sub.3 Bu-s Me CH.sub.2 H O 70-71 1-58 CF.sub.3 Bu-s Me CH.sub.2 4-F O 84-85 1-59 CF.sub.3 Bu-s Me CH.sub.2 4-Cl O 73-75 1-60 CF.sub.3 Bu-s Me CH.sub.2 4-Me O 61-64 1-61 CF.sub.3 Pr-i Et CH.sub.2 4-Me O 92-94 1-62 CF.sub.3 Pr-i Pr CH.sub.2 4-Me O 83-86 1-63 CF.sub.3 Pr-i Pr CH.sub.2 H O 146-147 1-64 CF.sub.3 Pr-i Me CH.sub.2 O H O 117-119 1-65 CF.sub.3 Pr-i Me CH.sub.2 O 4-Cl O 141-142

TABLE 3 Dia- m.p. (.degree. C.) Compound stereo- or refractive No. R.sup.1 R.sup.2 R.sup.3 Z Xn Q mer index (n.sub.D.sup.20) 1-66 CF.sub.3 Pr-i Me CH.sub.2 3-F O 120-123 1-67 CF.sub.3 Pr-i Me CH.sub.2 4-Et O 56-58 1-68 CF.sub.3 Pr-i Me CH.sub.2 4-Pr-i O 86-87 1-69 Pr-i Pr-i Me CH.sub.2 S H O 1-70 CF.sub.8 Pr-i Me CH.sub.2 3-Br O 120-121 1-71 CF.sub.3 Pr-i Me CH(Me) 4-Cl O 1.5232 1-72 CF.sub.3 Pr-i Me