WO2000021936A1

WO2000021936A1 - Uracil herbicides

Info

Publication number: WO2000021936A1
Application number: PCT/JP1999/005595
Authority: WO
Inventors: Yuzuru Sanemitsu; Yoshitomo Tohyama
Original assignee: Sumitomo Chemical Company, Limited
Priority date: 1998-10-12
Filing date: 1999-10-12
Publication date: 2000-04-20
Also published as: AU6007099A

Abstract

Uracil compounds of general formula (i) wherein R1 is hydrogen, halogen, cyano, or alkyl; R2 is alkyl, haloalkyl, alkenyl, alkynyl, N(R61)R62, or N=C(R61)R62, wherein R?61 and R62¿ are the same or different and independently hydrogen, alkyl, or haloalkyl; R3 is alkyl or haloalkyl; or R?2 and R3¿ may be combined at their ends to form optionally fluorine-substituted trimethylene or optionally fluorine-substituted tetramethylene; Q is optionally substituted phenyl; and X, Y, and Z are the same or different and independently oxygen or sulfur, have excellent herbicidal activity.

Description

URACIL HERBICIDES

Technical Field

The present invention relates to 3-phenyloxyuracil and 3-phenylthio- uracil compounds, their use, and intermediates for their production.

Disclosure of Invention The present inventors have extensively studied to find compounds having excellent herbicidal activity. As a result, they have found that uracil compounds of the general formula depicted below have excellent herbicidal activity, thereby completing the present invention.

Thus, the present invention provides uracil compounds of the general formula:

(hereinafter referred to as the present compound(s)) wherein R¹ is hydrogen, halogen, cyano, or C^C., alkyl;

R² is C_rC₃ alkyl, C_rC₃ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, N(R⁶¹)R⁶², or N=C(R⁶¹)R⁶², wherein R⁶¹ and R⁶² are the same or different and independently hydrogen, 0,-0₃ al yl. or Cι-C₃ haloalkyl; R³ is Cj-C_a alkyl or C,-C₃ haloalkyl; or

R² and R³ may be combined at their ends to form optionally fluorine- substituted trimethylene or optionally fluorine-substituted tetramethylene; is optionally substituted phenyl; and X, Y, and Z are the same or different and independently oxygen or sulfur; and herbicides containing these compounds as active ingredients.

The present invention further provides uracil compounds useful as the intermediates for the production of the present compounds, that is, uracil compounds of the general formula:

(hereinafter referred to as intermediate(s) A) wherein E¹, R³, Q, X, Y, and Z are as defined above; and uracil compounds of the general formula:

(hereinafter referred to as intermediate^) B) wherein R¹, X, Y, and Z are as defined above; R²⁰⁰ is hydrogen,

alkyl, Ci-C_a haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, or N(R⁶¹)R⁶² wherein R⁶¹ and R⁶² are as defined above; R³⁰⁰ is 0,-0, haloalkyl; or R²⁰⁰ and R³⁰⁰ may be combined at their ends to form optionally fluorine-substituted trimethylene or optionally fluorine-substituted tetramethylene.

Mode for Carrying Out the Invention For the elements or groups represented by R¹, halogen may include fluorine, chlorine, bromine, and iodine; and C,-C₃ alkyl may include methyl, ethyl, propyl, and isopropyl.

For the groups represented by R², C,-C₃ alkyl may include methyl, ethyl, propyl, and isopropyl; Cj-Cg haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, and 1,1-difluoroethyl; C₃-C₆ alkenyl may include allyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; and C₃-C₆ alkynyl may include propargyl, l-methyl-2-propynyl, 2-butynyl, 3-butynyl, and l,l-dimethyl-2-propynyl.

For the groups represented by R³, Ci-Cg alkyl may include methyl, ethyl, propyl, and isopropyl; and C,-C₃ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, pentafluoroethyl, and 1,1-difluoroethyl.

For the groups represented by R² and R³ which are combined at their ends, optionally fluorine-substituted trimethylene may include trimethylene, 1,1,2-trifluorotrimethylene, and 2,3,3-trifluorotrimethylene; and optionally fluorine-substituted tetramethylene may include tetramethylene. For the groups represented by R⁶¹ or R⁶², C,-C₃ alkyl may include methyl, ethyl, propyl, and isopropyl; and C,-C₃ haloalkyl may include trichloromethyl, trifluoromethyl, difluoromethyl, and chlorodifluoromethyl.

For the groups represented by Q, optionally substituted phenyl may include groups of the general formula:

wherein R⁴ is hydrogen, halogen, C^ , alkyl, or C,-C₃ haloalkyl;

R⁵ is hydrogen, halogen, N0₂, CN, C C₃ alkoxy, C_rC₃ alkyl, or C -C₃ haloalkyl;

R⁶ is hydrogen, halogen, 0,-0; alkyl, C,-C₆ haloalkyl, OR⁹, SR¹⁰, N(Rⁿ)R¹², COOR¹³, COOM, COR¹⁴, SO₂R¹⁵, N0₂, CN, CR²⁰=C(R¹⁶)R¹⁷, or CR¹⁸=NOR¹⁹;

R⁷ is hydrogen, halogen, C,-C₆ alkyl, C,-C₆ haloalkyl, hydroxy C,-C, alkyl, C,-C₆ alkoxy C,-C₆ alkyl, OR³⁹, SR⁴⁰, N(R⁴¹)R⁴², COOR⁴³, COOM, COR 44

S0₂R⁴⁵, N0₂, CN, CR^COHR⁴⁷, or CR⁴⁸=NOR⁴⁹; and R⁸ is hydrogen, halogen, C,-C₆ alkyl, C^C_e haloalkyl, hydroxy Ci-C_e alkyl, C C₆ alkoxy C,-C₆ alkyl, OR⁶⁹, SR⁷⁰, N(R⁷¹)R⁷², NR⁷¹N(R⁷⁰)R⁷²,

NR⁷¹OR⁶⁹, COOR⁷³, COOM, COR⁷⁴, SO₂R⁷⁵, NO₂, CN, CR⁸⁰=C(R⁷⁶)R⁷⁷, or

CR⁷⁸=NOR⁷⁹; wherein R⁹, R³⁹, and R⁶⁹ are the same or different and independently hydrogen, 0,-0,₀ alkyl, C, -C₁₀ haloalkyl, C₃-C₈ alkenyl, C₃-C₈ halo- alkenyl, C₃-C₈ alkynyl, C₃-C₈ haloalkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkenyl, C₃-C₁₀ cycloalkyl C,-C₃ alkyl, C₃-C₁₀ halocycloalkyl C_rC₃ alkyl, C₃-C₁₀ cycloalkenyl Cj-C_a alkyl, C₃-C₁₀ halocycloalkenyl

alkyl, (Ci-Cs alkyl)carbonyl, (C_!-C₅ haloalkyl)carbonyl, (C₃-C₆ cycloalkyl)carbonyl,

(C₃-C₆ halocycloalkyl)carbonyl, (Ci-C_e alkyl)carbonyl

alkyl, (C C₆ haloalkyl)carbonyl C,-C₆ alkyl, (C_rC₆ alkoxy)carbonyl, (Ci-C_e haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃-C₁₀ halocyclo- alkoxy)carbonyl, carboxy C,-C₅ alkyl, (hydroxy Cj-Cg alkoxy)carbonyl C,-C₅ alkyl, (C,-C₁₀ alkoxy)carbonyl C,-C₅ alkyl,

haloalkoxy)- carbonyl C,-C₅ alkyl, tetrahydrofuranyloxycarbonyl C,-C₆ alkyl, tetrahydropyranyloxycarbonyl Cj-C_e alkyl, {(Ci-C_e alkoxy) C_j-Cβ alkoxy}carbonyl C,-C₆ alkyl, [{(Cj-Cg alkoxy)carbonyl} C_rC₆ alkoxy]- carbonyl C,-C₆ alkyl, [2-aza-2-(C_rC₃ alkoxy)- 1-{(C,-C₃ alkoxy)- carbonyl}vinyl] C^ , alkyl, (C₃-C₁₀ cycloalkoxy)carbonyl C_rC₅ alkyl,

(C₃-C₁₀ halocycloalkoxy)carbonyl C C₅ alkyl, aminocarbonyl C^C_Q alkyl, (C,-C₆ alkylamino)carbonyl C,-C₆ alkyl, (C₃-C₈ alkenyloxy)- carbonyl Ci-C_e alkyl, (C₃-C₈ alkynyloxy)carbonyl C,-C₆ alkyl, hydroxy Ci-C_e alkyl, C_rC₆ alkoxy C_rC₆ alkyl, C,-C₆ haloalkoxy Cj-Cg alkyl, mercapto C,-C₆ alkyl, Cj-Cg alkylthio

alkyl, Cj-Cg haloalkylthio Ci-Cg alkyl, cyano C C₄ alkyl, tetrahydrofuranyl, tetrahydropyranyl, optionally substituted phenyl, (optionally substituted phenyl) C^C_g alkyl, optionally substituted phenylcarbonyl, or SO₂R²²;

R¹⁰, R⁴⁰, and R⁷⁰ are the same or different and independently hydrogen, CyC^ alkyl, C,-C₁₀ haloalkyl, C₃-C₈ alkenyl, C₃-C₈ halo- alkenyl, C₃-C₈ alkynyl, C₃-C₈ haloalkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkenyl, C₃-C₁₀ cycloalkyl C, -C₃ alkyl, C₃-C₁₀ halocycloalkyl C_rC₃ alkyl, C₃-C₁₀ cycloalkenyl C_rC₃ alkyl, C₃-C₁₀ halocycloalkenyl CyCg alkyl, (C^C_s alkyl)carbonyl, (CyC_s haloalkyl)carbonyl, (C₃-C₆ cycloalkyl)carbonyl, (C₃-C₆ halocycloalkyl)carbonyl, (C C₆ alkyl)carbonyl C, -C₆ alkyl, (Cj-Cg haloalkyl)carbonyl Cj-Cg alkyl,

haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃-C₁₀ halocyclo- alkoxy)carbonyl, carboxy C,-C₅ alkyl, (hydroxy

alkoxy)carbonyl C_rC₅ alkyl, (C,-C₁₀ alkoxy)carbonyl C,-C₅ alkyl, (C,-C₁₀ haloalkoxy)- carbonyl C_rC₅ alkyl, {(C C₆ alkoxy) C C₆ alkoxy}carbonyl Cj-Cg alkyl, (C₃-C₁₀ cycloalkoxy)carbonyl Cj-C₃ alkyl, (C₃-C₁₀ halocyclo- alkoxy)carbonyl C_J-C_B alkyl, aminocarbonyl Ci-Cg alkyl, (C,-C₆ alkyl- amino)carbonyl Cj-Cg alkyl, hydroxy

alkyl, C,-C₆ alkoxy C_rC₆ alkyl, C,-C₆ haloalkoxy CyCβ alkyl, mercapto Cj-Cg alkyl, Cj-Cβ alkylthio C,-C₆ alkyl, Ci-Cg haloalkylthio Cj-Cg alkyl, cyano C C₄ alkyl, tetrahydrofuranyl, tetrahydropyranyl, optionally substituted phenyl, (optionally substituted phenyl) C_!-C₃ alkyl, or optionally substituted phenylcarbonyl;

R^u, R¹², R⁴¹, R⁴², R⁷¹, and R⁷² are the same or different and independently hydrogen, C,-C_ι0 alkyl, C^C^ haloalkyl, C₃-C₈ alkenyl, C₃-C₈ haloalkenyl, C₃-C₈ alkynyl, C₃-C₈ haloalkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkenyl, C₃-C₁₀ cycloalkyl C_rC₃ alkyl, C₃-C₁₀ halocycloalkyl

alkyl, C₃-C₁₀ cycloalkenyl C_j-Cg alkyl, C₃-C₁₀ halocycloalkenyl C_rC₃ alkyl, (C_rC₅ alkyl)carbonyl, (C,-C₅ haloalkyl)carbonyl, (C₃-C₆ cycloalkyl)carbonyl,

(C₃-C₆ halocycloalkyl)carbonyl, (C,-C₆ alkyl)carbonyl C,-C₆ alkyl, (Ci-Cg haloalkyl)carbonyl C,-C₆ alkyl,

alkoxy)carbonyl,

haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C_a-C₁₀ halo- cycloalkoxy)carbonyl, carboxy Cj-Cg alkyl, (hydroxy C,-C_ε alkoxy)- carbonyl C^C_s alkyl, (C, -C₁₀ alkoxy)carbonyl C C₅ alkyl, (C, -C₁₀ haloalkoxy)carbonyl Cj-Cg alkyl, (C₃-C₁₀ cycloalkoxy)carbonyl C_j-Cg alkyl, (C₃-C₁₀ halocycloalkoxy)carbonyl Cj-C₃ alkyl, aminocarbonyl Cj-Cg alkyl,

alkylamino)carbonyl

alkyl, hydroxy CyCg alkyl, C C₆ alkoxy C_rCg alkyl, C, -C₆ haloalkoxy C C₆ alkyl, mercapto Ci-Cg alkyl, {(C_ι-C₆ alkoxy) Cj-Cg alkoxy}carbonyl C_j-Cg alkyl, C,-C₆ alkylthio C_rC₆ alkyl, C_rC₆ haloalkylthio C, -C₆ alkyl, cyano C,-C₄ alkyl, optionally substituted phenyl, (optionally substituted phenyl) Cj-Cg alkyl, (optionally substituted phenyl)((C, -C₁₀ alkoxy)carbonyl) C,-C₃ alkyl, optionally substituted phenylcarbonyl, SR³⁴, SOR²¹, or SO₂R²²;

R¹³, R⁴³, and R⁷³ are the same or different and independently hydrogen, C^C^ alkyl, C_rC₁₀ haloalkyl, C₃-C₁₀ alkenyl, C₃-C₁₀ haloalkenyl, C₃-C₁₀ alkynyl, C₃-C₁₀ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, N(R²³)R²⁴, N=C(R²³)R²⁴, tetrahydrofuranyl, tetra- hydropyranyl, carboxy C C₅ alkyl, (C₃-C₈ cycloalkoxy)carbonyl Cj-C₃ alkyl, (C₃-C₈ alkenyloxy)carbonyl

alkyl, (C₃-C₈ alkynyloxy)- carbonyl C, -C₆ alkyl, tetrahydrofuranyloxycarbonyl C, -C₆ alkyl, tetrahydropyranyloxycarbonyl C,-C₆ alkyl, (Cj-Cg alkoxy) carbonyl C_j-Cg alkyl, or (C_ι-C₅ haloalkoxy)carbonyl Ci-Cg alkyl;

R¹⁴, R⁴⁴, and R⁷⁴ are the same or different and independently hydrogen, chlorine, Cj-Cg alkyl, Cj-Cg haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, or N(R²⁵)R²⁶; R¹⁵, R⁴⁵, and R⁷⁵ are the same or different and independently chlorine, d-Cu alkyl, d-d_o haloalkyl, N(R²⁷)R²⁸, or OR²⁹;

R¹⁶, R⁴⁶, and R⁷⁶ are the same or different and independently hydrogen, halogen, or Cj-C₃ alkyl;

R¹⁷, R⁴⁷, and R⁷⁷ are the same or different and independently hydrogen, COOR³⁰, cyano, or C_ι-C₅ alkyl;

R¹⁸, R⁴⁸, and R⁷⁸ are the same or different and independently hydrogen, C_ι-C₄ alkyl, Ci-C₄ haloalkyl, C₃-C₆ cycloalkyl, or C₃-C₆ halocycloalkyl;

R¹⁹, R⁴⁹, and R⁷⁹ are the same or different and independently hydrogen, Ci-C₁₀ alkyl, C_ι-C₁₀ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₃-C₁₀ cycloalkyl d-C₃ alkyl, C₃-C₁₀ halocycloalkyl C_ι-C₃ alkyl, C₃-C₅ alkenyl, C₃-C₅ haloalkenyl, C₃-C₅ alkynyl, C₃-C₅ haloalkynyl, carboxy d-C₃ alkyl, (Ci-Cg alkoxy)carbonyl Ci-C₃ alkyl, (Ci-C₅ haloalkoxy)carbonyl C_ι-C₃ alkyl, optionally substituted phenyl, or (optionally substituted phenyl) C_ι-C₃ alkyl;

R²⁰, R⁵⁰, and R⁸⁰ are the same or different and independently hydrogen, chlorine, Cj-Cg alkyl, Ci-C₅ haloalkyl, C₃-C₆ cycloalkyl, or C₃-C₆ halocycloalkyl; and

M is an alkali metal; wherein R³⁴ is d-C₁₀ alkyl, Cι-C₁₀ haloalkyl, or optionally substituted phenyl;

R²¹ is Cj-Ci_o alkyl, d-Ci_o haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, or optionally substituted phenyl; R²² is Ci-Cio alkyl, C_rC₁₀ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, or optionally substituted phenyl;

R²³ is hydrogen or Cι-C_ε alkyl;

R²⁴ is hydrogen, Ci-Cg alkyl, C_ι-C₅ haloalkyl or optionally substituted phenyl;

R²⁵ is hydrogen, d-Cι₀ alkyl, d-C₁₀ haloalkyl, SO₂H,

Cj-Cg alkylsulfonyl, C₃-C_ι0 cycloalkyl, C₃-C₁₀ halocycloalkyl, carboxy C_ι-C₃ alkyl, (Ci-C₅ alkoxy)carbonyl d-C₃ alkyl, optionally substituted phenyl, d-C₁₀ alkylsulfinyl, C_ι-C₁₀ halo alkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₃-C₈ halocyclo- alkylsulfinyl, optionally substituted phenylsulfinyl, C_ι-C₁₀ alkylsulfonyl, d-C₁₀ haloalkylsulfonyl, C₃-C₈ cycloalkyl- sulfonyl, C₃-C₈ halocycloalkylsulfonyl, or optionally substituted phenylsulfonyl; R²⁶ is hydrogen, d-C₁₀ alkyl, or Ci-C_ι0 haloalkyl;

R²⁷ is hydrogen, d-C₅ alkyl, or C_ι-C₅ haloalkyl;

R²⁸ is hydrogen, d-C₁₀ alkyl, or Ci-Cj_o haloalkyl;

R²⁹ is C_ι-C₁₀ alkyl; and

R³⁰ is hydrogen, d-C₁₀ alkyl, C C₁₀ haloalkyl, C₃-C 10 cycloalkyl, C₃-C₁₀ halocycloalkyl, or optionally substituted phenyl.

For the elements or groups represented by R⁴, halogen may include fluorine, chlorine, bromine, and iodine; d-C₃ alkyl may include methyl, ethyl, propyl, and isopropyl; and d-C₃ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, and 1,1-difluoroethyl.

For the elements or groups represented by R⁵, halogen may include fluorine, chlorine, bromine, and iodine; C_ι-C₃ alkoxy may include methoxy, ethoxy, propoxy, and isopropoxy; C_ι-C₃ alkyl may include methyl, ethyl, propyl, and isopropyl; and C_rC₃ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, and 1,1-difluoroethyl. For the elements or groups represented by R⁶, halogen may include fluorine, chlorine, bromine, and iodine; d-C₆ alkyl may include methyl, ethyl, isopropyl, normal (hereinafter abbreviated to n-) pentyl, and n-butyl; and Ci-Cg haloalkyl may include chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 1,1-difluorohexyl, 3,3,3-trifluoropropyl, and 5,5,5, 1,1-pentafluoropentyl.

For the elements or groups represented by R⁷, halogen may include fluorine, chlorine, bromine, and iodine; C_ι-C₆ alkyl may include methyl, ethyl, isopropyl, n-pentyl, and n-butyl; Ci-Cg haloalkyl may include chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 1,1-difluorohexyl, 3,3,3-trifluoropropyl, and 5,5,5, 1,1-pentafluoropentyl; hydroxy Ci-Cg alkyl may include hydroxy - methyl and 2-hydroxyethyl; and d-C₆ alkoxy Ci-Cg alkyl may include methoxymethyl, ethoxymethyl, 2-methoxyethyl, and 2-ethoxyethyl.

For the elements or groups represented by R⁸, halogen may include fluorine, chlorine, bromine, and iodine; Cj-Cg alkyl may include methyl, ethyl, isopropyl, n-pentyl, and n-butyl; C_ι-C₆ haloalkyl may include chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 1,1-difluorohexyl, 3,3,3-trifluoropropyl, and 5,5,5, 1,1-pentafluoropentyl; hydroxy Cj-Cg alkyl may include hydroxy- methyl, 1 -hydroxy ethyl, and 2-hydroxyethyl; and d-C₆ alkoxy Ci-Cg alkyl may include methoxymethyl, ethoxymethyl, 2-methoxyethyl, and 2-ethoxy- ethyl.

For the groups represented by R⁹, R³⁹, or R⁶⁹, d-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, 2-butyl, isoamyl, and n-octyl; d-C₁₀ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 2,2,2-trifJuoroethyl, 5-chloro-n-amyl, and 7-bromoheptyl; C₃-C₈ alkenyl may include allyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 3-butenyl,2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C₃-C₈ haloalkenyl may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl; C₃-C₈ alkynyl may include propargyl, l-methyl-2- propynyl, 2-butynyl, 3-butynyl, and l,l-dimethyl-2-propynyl; C₃-C₈ haloalkynyl may include 3-iodo-2-propynyl and 3-bromo-2-propynyl; C₃-C_ι0 cycloalkyl may include cyclopropyl, cyclopentyl, cyclohexyl, and 4,4-dimethyl- cyclohexyl; C₃-Cι₀ halocycloalkyl may include 2-fluorocyclopentyl and 3,4- dichlorocyclohexyl; C₃-C_ι0 cycloalkenyl may include 2-cyclohexenyl; C₃-C_ι0 halocycloalkenyl may include 4-chloro-2-cyclohexenyl; C₃-C_ι0 cycloalkyl Cι-C₃ alkyl may include cyclopropylmethyl, cyclop entylm ethyl, and cyclohexyl - ethyl; C₃-C_ι0 halocycloalkyl Cι-C₃ alkyl may include 2-fluoroc clopentyl- methyl and 3,4-dichlorocyclohexylethyl; C₃-C₁₀ cycloalkenyl d-C₃ alkyl may include 2-cyclohexenylmethyl; C₃-C_ι0 halocycloalkenyl C_ι-C₃ alkyl may include 4-chloro-2-cyclohexenylmethyl; (C_ι-C₅ alkyl) carbonyl may include methylcarbonyl, ethylcarbonyl, and propylcarbonyl; (Cj-Cg haloalkyl)- carbonyl may include chloromethylcarbonyl, fluoromethylcarbonyl, trifluoro- methylcarbonyl, dichloromethylcarbonyl, pentafluoropropylcarbonyl, and 2-chloroethylcarbonyl; (C₃-C₆ cycloalkyl)carbonyl may include cyclopropyl- carbonyl; (C₃-C₆ halocycloalkyl)carbonyl may include 2-fluorocyclopentyl- carbonyl, 2,2-difluorocyclopentylcarbonyl, and 3,4-dichlorocyclohexyl- carbonyl; (Ci-C₆ alkyl)carbonyl Cj-Cg alkyl may include methylcarbonyl- methyl and ethylcarbonylmethyl; (C_j-Cg haloalkyl)carbonyl C_ι-C₆ alkyl may include f uoromethylcarbonylmethyl, 2-chloroethylcarbonylmethyl, 2-fluoroethylcarbonylmethyl, and trifluoromethylcarbonylmethyl; (C_ι-C₆ alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, propoxy- carbonyl, t-butoxycarbonyl, butoxycarbonyl, amyloxycarbonyl, isopropoxy- carbonyl, isobutoxycarbonyl, and isoamyloxycarbonyl; (d-C₆ haloalkoxy)- carbonyl may include chloromethyloxycarbonyl, 2-fluoroethyloxycarbonyl, 2-chloropropyloxycarbonyl, 3-chlorobutyloxycarbonyl, l-chloro-2-propyloxy- carbonyl, l,3-dichloro-2-propyloxycarbonyl, 2,2-dichloroethyloxycarbonyl, 2,2,2-trifluoroethyloxycarbonyl, and 2,2,2-trichloroethyloxycarbonyl; (C₃-C₁₀ cycloalkoxy)carbonyl may include cyclop ropyloxycarb on yl, cyclobutyloxy- carbonyl, cyclopentyloxycarbonyl, and cyclohexyloxycarbonyl; (C₃-C₁₀ halo- cycloalkoxy)carbonyl may include 2-fluorocyclopentyloxycarbonyl, and 3,4- dichlorocyclohexyloxycarbonyl; carboxy d-C₅ alkyl may include carboxy- methyl, 2-carboxyethyl, and 1-carboxyethyl; (hydroxy C_ι-C₅ alkoxy)carbonyl Ci-C₅ alkyl may include hydroxymethoxycarbonylmethyl, 2-(hydroxy- methoxycarbonyl)ethyl, 2-hydroxyethoxycarbonylmethyl, 2-(2-hydroxy- ethoxycarbonyl)ethyl, and l-(2-hydroxyethoxycarbonyl)ethyl; (d-C₁₀ alkoxy)- carbonyl C_rC₅ alkyl may include methoxycarbonylmethyl, ethoxycarbonyl- methyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonyl- methyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxy- carbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, and 1-isoamyloxy- carbonylethyl; (C_ι-C_ι0 haloalkoxy)carbonyl d-C₅ alkyl may include chloro- methyloxycarbonylmethyl, 2-fJuoroethyloxycarbonylmethyl, 2-chloropropyl- oxycarbonylmethyl, 3-chlorobutyloxycarbonylm ethyl, l-chloro-2-propyloxy- carbonylmethyl, l,3-dichloro-2-propyloxycarbonylmethyl, 2,2-dichloroethyl- oxycarbonylmethyl, 2,2,2-trifluoroethyloxycarbonylmethyl, and 2-(2,2,2- trichloroethyloxycarbonyl) ethyl; tetrahydrofuranyloxycarbonyl C_rC₆ alkyl may include 2-tetrahydrofuranyloxycarbonylmethyl, 3-tetrahydrofuranyl- oxycarbonylmethyl, l-(2-tetrahydrofuranyloxycarbonyl)ethyl, l-(3-tetra- hydrofuranyloxycarbonyl)ethyl, 2 -(2 -tetrahydrofuran yloxycarbonyl)ethyl, and 2-(3-tetrahydrofuranyloxycarbonyl)ethyl; tetrahydropyranyloxycarbonyl C_ι- C₆ alkyl may include 2 -tetrahydropyranyloxycarbonylmethyl, 3-tetrahydropyranyloxycarbonylmethyl, l-(2-tetrahydrop ranyloxy- carbonyl)ethyl, l-(3-tetrahydropyranyloxycarbonyl)ethyl, 2-(2-tetrahydro- pyranyloxycarbonyl)ethyl, and 2-(3-tetrahydropyranyloxycarbonyl)ethyl; {(C_ι-C₆ alkoxy) Cj-Cg alkoxy} carbonyl Ci-Cg alkyl may include methoxy- methoxycarbonylmethyl, 2-(methoxymethoxycarbonyl)ethyl, l-(methoxy- methoxycarbonyl)ethyl, l-(ethoxymethoxycarbonyl)ethyl, l-(propoxy- methoxycarbonyl)ethyl, l-(isopropoxymethoxycarbonyl)ethyl, l-(l-methoxy- ethoxycarbonyl)ethyl, l-(l-ethoxyethoxycarbonyl)ethyl, l-(2-methoxy- ethoxycarbonyl)ethyl, l-(2-ethoxyethoxycarbonyl)ethyl, l-(2-propoxyethoxy- carbonyl)ethyl, l-(2-isopropoxyethoxycarbonyl)ethyl, 2-(2-methoxyethoxy- carbonyl)ethyl, 2-(2-ethoxyethoxycarbonyl)ethyl, 2-(2-propoxyethoxy- carbonyl)ethyl, and 2-(2-isopropoxyethoxycarbonyl)ethyl; [{(Ci-Cg alkoxy)- carbonyl} Ci-C₆ alkoxy]carbonyl Cι-C₆ alkyl may include {(methoxy- carbonyl)methoxycarbonyl}methyl, 2-{(methoxycarbonyl)methoxycarbonyl}- ethyl, 2-{l-(methoxycarbonyl)ethoxycarbonyl}ethyl, and 2-{l-methyl- l- (methoxycarbonyl)ethoxycarbonyl}ethyl; [2-aza-2-(C_ι-C₃ alkoxy)- l-{(C_ι-C₃ alkoxy)carbonyl}vinyl] C_ι-C₃ alkyl may include 3-aza-3-methoxy-2-methoxy- carbonyl-3-propenyl, 3-aza-3-ethoxy-2-methoxycarbonyl-3-propenyl, 3-aza-3- methoxy-2-ethoxycarbonyl-3-propenyl, and 3-aza-3-ethoxy-2-methoxy- carbonyl-3-propenyl; (C₃-C_ι0 cycloalkoxy)carbonyl C_ι-C₅ alkyl may include cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyl- oxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonyl- ethyl, 1-cyclopentyloxycarbonylethyl, 1-cyclohexyloxycarbonylethyl, 2-cyclo- butyloxycarbonylethyl, 2-cyclopentyloxycarbonylethyl, and 2-cyclohexyloxy- carbonylethyl; (C₃-C_ι0 halocycloalkoxy)carbonyl C_ι-C₅ alkyl may include 2-fluorocyclopentyloxycarbonylmethyl and 2-(3,4-dichlorocyclohexyloxy- carbonyl)ethyl; aminocarbonyl C_ι-C₆ alkyl may include aminocarbonylmethyl, 1-aminocarbonylethyl, and 2-aminocarbonylethyl; (Cj-Cg alkylamino)- carbonyl d-C₆ alkyl may include methylaminocarbonylmethyl, ethylamino- carbonylmethyl, 1-methylaminocarbonylethyl, l-(ethylaminocarbonyl)ethyl, l-(propylaminocarbonyl)ethyl, 2-methylaminocarbonylethyl, and 2-(ethyl- aminocarbonyl)ethyl; (C₃-C₈ alkenyloxy)carbonyl C_ι-C₆ alkyl may include allyloxycarbonylmethyl, l-methyl-2-propenyloxycarbonylmethyl, 2-methyl- 2-propenyloxycarbonylmethyl, 2-butenyloxycarbonylmethyl, 1-allyloxy- carbonylethyl, l-(2-methyl-2-propenyloxycarbonyl)ethyl, 2-allyloxycarbonyl- ethyl, and 2-(2-methyl-2-propenyloxycarbonyl)ethyl; (C₃-C₈ alkynyloxy)- carbonyl Cj-Cg alkyl may include propargyloxycarbonylmethyl, l-methyl-2- propynyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, l-(l-methyl-2- propynyloxycarbonyl)ethyl, 2-propargyloxycarbonylethyl, and 2-(l-methyl-2- propynyloxycarbonyl)ethyl; hydroxy Cι-C₆ alkyl may include hydroxymethyl, 1-hydroxyethyl, and 2-hydroxyethyl; d-C₆ alkoxy C_rC₆ alkyl may include methoxymethyl, 1-methoxyethyl, and ethoxymethyl; Ci-Cg haloalkoxy -Cg alkyl may include 2,2,2-trifTuoroethoxymethyl; mercapto C_ι-C₆ alkyl may include mercaptomethyl, 1-mercaptoethyl, and 2-mercaptoethyl; C_ι-C₆ alkylthio C_ι-C₆ alkyl may include methylthiomethyl, 1-methylthioethyl, and ethylthiomethyl; d-C₆ haloalkylthio C_ι-C₆ alkyl may include 2,2,2-trifluoro- ethylthiomethyl; cyano C_rC₄ alkyl may include cyanomethyl, cyanoethyl, and 1-methylcyanoethyl; tetrahydrofuranyl may include 2-tetrahydrofuranyl and 3-tetrahydrofuranyl; tetrahydropyranyl may include 2-tetrahydro- pyranyl and 3-tetrahydropyranyl; optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifJuoromethylphenyl, 2-methoxy- phenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-trifJuoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, and 2,5- dichlorophenyl; (optionally substituted phenyl) Ci-Cg alkyl may include benzyl, phenethyl, 1-methylbenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chloro- benzyl, 2-methoxybenzyl, 3-methoxybenzyl, and 4-methoxybenzyl; and optionally substituted phenylcarbonyl may include benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2,3-dichlorobenzoyl, 2,4-dichlorobenzoyl, 2,5-dichlorobenzoyl, 2,6-dichlorobenzoyl, and 3,4-dichlorobenzoyl.

For the groups represented by R¹⁰, R⁴⁰, or R⁷⁰, Ci-C_ι0 alkyl may include methyl, ethyl, isopropyl, n-butyl, 2-butyl, isoamyl, and n-octyl; C_ι-C₁₀ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 2,2,2-trifiuoroethyl, 5-chloro-n-amyl, and 10-bromoheptyl; C₃-C₈ alkenyl may include allyl, l-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C₃-C₈ haloalkenyl may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl; C₃-C₈ alkynyl may include propargyl, l-methyl-2-propynyl, 2-butynyl, 3-butynyl, and l, l-dimethyl-2-propynyl; C₃-C₈ haloalkynyl may include 3-iodo-2-propynyl, and 3-bromo-2-propynyl; C₃-C₁₀ cycloalkyl may include cyclopropyl, cyclopentyl, cyclohexyl, and 4,4-dimethylcyclohexyl; C₃-C₁₀ halo- cycloalkyl may include 2-fluorocyclopentyl and 3,4-dichlorocyclohexyl; C₃-C_ι0 cycloalkenyl may include 2-cyclohexenyl; C₃-C_ι0 halocycloalkenyl may include 4-chloro-2-cyclohexenyl; C₃-Cι₀ cycloalkyl C_ι-C₃ alkyl may include cyclopropylmethyl, cyclop en tylmethyl, and cyclohexylethyl; C₃-Cι₀ halocycloalkyl C_ι-C₃ alkyl may include 2-fluorocyclopentylmethyl and 2-(3,4-dichloro- cyclohexyl)ethyl; C₃-C_ι0 cycloalkenyl Cι-C₃ alkyl may include 2-cyclohexenylmethyl; Cg-Ci_o halocycloalkenyl C_ι-C₃ alkyl may include 4-chloro-2-cyclo- hexenylmethyl; (C_ι-C₅ alkyl)carbonyl may include methylcarbonyl, ethyl- carbonyl, and propylcarbonyl; (Ci-Cg haloalkyl)carbonyl may include chloro- methylcarbonyl, fluoromethylcarbonyl, trifluoromethylcarbonyl, dichloro- methylcarbonyl, pentafluoropropylcarbonyl, and 2-chloroethylcarbonyl; (C₃-C₆ cycloalkyl)carbonyl may include cyclopropylcarbonyl; (C₃-C₆ halocyclo- alkyl)carbonyl may include 2-fluorocyclopentylcarbonyl, 2,2-difluorocyclo- pentylcarbonyl, and 3,4-dichlorocyclohexylcarbonyl; (C_ι-C₆ alkyl)carbonyl d- alkyl may include methylcarbonylmethyl, ethylcarbonylmethyl, and ethylcarbonylmethyl; (C_ι-C₆ haloalkyl)carbonyl Ci-Cg alkyl may include fluorom ethylcarbonylmethyl, 2-chloroethylcarbonylmethyl, 2-fluoroethyl- carbonylmethyl, and 3,3,3-trifluoromethylcarbonylmethyl; (d-C₆ alkoxy)- carbonyl may include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, t-butoxycarbonyl, butoxycarbonyl, amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and isoamyloxycarbonyl; (C_ι-C₆ haloalkoxy)carbonyl may include chloromethyloxycarbonyl, 2-fluoroethyloxycarbonyl, 2-chloropropyl- oxycarbonyl, 3-chlorobutyloxycarbonyl, l-chloro-2-propyloxycarbonyl, 1,3-di- chloro-2-propyloxycarbonyl, 2,2-dichloroethyloxycarbonyl, 2,2,2-trifiuoro- ethyloxycarbonyl, and 2,2,2-trichloroethyloxycarbonyl; (C₃-Cι₀ cycloalkoxy)- carbonyl may include cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclo- pentyloxycarbonyl, and cyclohexyloxycarbonyl; (C₃-C_ι0 halocycloalkoxy)- carbonyl may include 2-fluorocyclopentyloxycarbonyl, and 3,4-dichlorocyclo- hexyloxycarbonyl; carboxy C_ι-C₅ alkyl may include carboxymethyl, 2-carboxyethyl, and 1-carboxyethyl; (hydroxy C_ι-C₅ alkoxy)carbonyl Cj-Cg alkyl may include hydroxymethoxycarbonylmethyl, 2-(hydroxymethoxy- carbonyl)ethyl, 2-hydroxyethoxycarbonylmethyl, 2-(2-hydroxyethoxy- carbonyl)ethyl, and l-(2-hydroxyethoxycarbonyl)ethyl; (C_ι-C₁₀ alkoxy)- carbonyl d- ₅ alkyl may include methoxycarbonylm ethyl, ethoxycarbonyl- methyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonyl- methyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxy- carbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, and 1-isoamyloxy- carbonylethyl; (d-C₁₀ haloalkoxy)carbonyl C_ι-C₅ alkyl may include chloro- methyloxycarbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloropropyl- oxycarbonylm ethyl, 3-chlorobutyloxycarbonylmethyl, l-chloro-2-propyloxy- carbonylmethyl, l,3-dichloro-2-propyloxycarbonylmethyl, 2,2-dichloroethyl- oxycarbonylmethyl, 2,2,2-trifluoroethyloxycarbonylmethyl, and 2,2,2-tri- chloroethyloxycarbonylethyl; {(C_ι-C₆ alkoxy) C_ι-C₆ alkoxy} carbonyl d-C₆ alkyl may include methoxymethoxycarbonylmethyl, 2-(methoxymethoxy- carbonyl)ethyl, l-(methoxymethoxycarbonyl)ethyl, l-(ethoxymethoxy- carbonyl)ethyl, l-(propoxymethoxycarbonyl)ethyl, l-(isopropoxymethoxy- carbonyl)ethyl, l-(l-methoxyethoxycarbonyl)ethyl, l-(l-ethoxyethoxy- carbonyl)ethyl, l-(2-methoxyethoxycarbonyl)ethyl, l-(2-ethoxyethoxy- carbonyl)ethyl, l-(2-propoxyethoxycarbonyl)ethyl, l-(2-isopropoxyethoxy- carbonyl)ethyl, 2-(2-methoxyethoxycarbonyl)ethyl, 2-(2-ethoxyethoxy- carbonyl)ethyl, 2-(2-propoxyethoxycarbonyl)ethyl, and 2-(2-isopropoxy- ethoxycarbonyl)ethyl; (C₃-C_ι0 cycloalkoxy)carbonyl C_ι-C₅ alkyl may include cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyl- oxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonyl- ethyl, 1-cyclopentyloxycarbonylethyl, and 1 -cyclohexyl oxycarbonylethyl; (C₃-Ci₀ halocycloalkoxy)carbonyl Cj-Cg alkyl may include 2-fluorocyclo- pentyloxycarbonylmethyl and 2-(3,4-dichlorocyclohexyloxycarbonyl)ethyl; aminocarbonyl d-C₆ alkyl may include aminocarbonylmethyl, 1-amino- carbonylethyl, and 2-aminocarbonylethyl; (Ci-Cg alkylamino)carbonyl C_ι-C₆ alkyl may include methylaminocarbpnylmethyl, ethylaminocarbonylmethyl, 1-methylaminocarbonylethyl, l-(ethylaminocarbonyl)ethyl, l-(propylamino- carbonyl)ethyl, 2-methylaminocarbonylethyl, and 2-(ethylaminocarbonyl)- ethyl; hydroxy C_ι-C₆ alkyl may include hydroxymethyl, 1 -hydroxy ethyl, and 2-hydroxyethyl; d-C₆ alkoxy Ci-Cg alkyl may include methoxymethyl, 1-methoxyethyl, and ethoxymethyl; C_ι-C₆ haloalkoxy C_rC₆ alkyl may include 2,2,2-trifJuoroethoxymethyl; mercapto C -C₆ alkyl may include mercapto- methyl, 1-mercaptoethyl, and 2-mercaptoethyl; Cj-Cg alkylthio d-C₆ alkyl may include methylthiomethyl, 1-methylthioethyl, and ethylthiomethyl; Cj-Cg haloalkylthio Ci-Cg alkyl may include 2,2,2-trifluoroethylthiomethyl; cyano C_ι-C₄ alkyl may include cyanomethyl, cyanoethyl, and 1-methyl- cyanoethyl; tetrahydrofuranyl may include 2 -tetrahydrofuranyl and 3-tetra- hydrofuranyl; tetrahydropyranyl may include 2 -tetrahydropyranyl and 3-tetrahydropyranyl; optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, and 2,5- dichlorophenyl; (optionally substituted phenyl) d-C₃ alkyl may include benzyl, phenethyl, 1-methylbenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chloro- benzyl, 2-methoxybenzyl, 3-methoxybenzyl, and 4-methoxybenzyl; and optionally substituted phenylcarbonyl may include benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2,3-dichlorobenzoyl, 2,4-dichlorobenzoyl, 2,5-dichlorobenzoyl, 2,6-dichlorobenzoyl, and 3,4-dichlorobenzoyl.

For groups represented by R¹¹, R¹², R⁴¹, R⁴², R⁷¹, or R⁷², C_rC₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, 2 -butyl, t-butyl, isoamyl, and n-octyl; d-C₁₀ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 2-fJuoroethyl, 2,2,2-trifluoroethyl, 5-chloro-n-amyl, and 7-bromoheptyl; C₃-C₈ alkenyl may include allyl, l-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C₃-C₈ haloalkenyl may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl; C₃-C₈ alkynyl may include propargyl, l-methyl-2- propynyl, 2-butynyl, 3-butynyl, and l, l-dimethyl-2-propynyl; C₃-C₈ haloalkynyl may include 3-iodo-2-propynyl and 3-bromo-2-propynyl; C₃-C₁₀ cyclo- alkyl may include cyclopropyl, cyclopentyl, cyclohexyl, and 4,4-dimethyl- cyclohexyl; C₃-C_ι0 halocycloalkyl may include 2-fluorocyclopentyl and 3,4-di- chlorocyclohexyl; C₃-C_ι0 cycloalkenyl may include 2-cyclohexenyl; C₃-C_ι0 halocycloalkenyl may include 4-chloro-2-cyclohexenyl; C₃-C_ι0 cycloalkyl d-C₃ alkyl may include cyclopropylmethyl, cyclop entylmethyl, and cyclohexyl- ethyl; C₃-d₀ halocycloalkyl C C₃ alkyl may include 2-fluorocyclopentyl- methyl and 3,4-dichlorocyclohexylethyl; C₃-C₁₀ cycloalkenyl C_ι-C₃ alkyl may include 2-cyclohexenylmethyl; C₃-C₁₀ halocycloalkenyl C_ι-C₃ alkyl may include 4-chloro-2-cyclohexenylmethyl; (C_ι-C₅ alkyl) carbonyl may include methylcarbonyl, ethylcarbonyl, and propylcarbonyl; (Cι-C₅ haloalkyl)- carbonyl may include chloromethylcarbonyl, fluoromethylcarbonyl, trifluoro- methylcarbonyl, dichloromethylcarbonyl, pentafluoropropylcarbonyl, and 2-chloroethylcarbonyl; (C₃-C₆ cycloalkyl)carbonyl may include cyclopropyl- carbonyl; (C₃-C₆ halocycloalkyl)carbonyl may include 2-fluorocyclopentyl- carbonyl, 2,2-difluorocyclopentylcarbonyl, and 3,4-dichlorocyclohexyl- carbonyl; (C_ι-C₆ alkyl)carbonyl Cj-Cg alkyl may include methylcarbonyl- methyl, ethylcarbonylmethyl, and ethylcarbonylmethyl; (C_ι-C₆ haloalkyl)- carbonyl Cj-Cg alkyl may include fluoromethylcarbonylmethyl, 2-chloroethylcarbonylmethyl, 2-fluoroethylcarbonylmethyl, and 3,3,3-trifluoro- methylcarbonylmethyl; (Cj-Cg alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, t-butoxy carbonyl, butoxycarbonyl, amyl- oxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and isoamyloxy- carbonyl; (C_ι-C₆ haloalkoxy)carbonyl may include chloromethyloxycarbonyl, 2-fluoroethyloxycarbonyl, 2-chloropropyloxycarbonyl, 3-chlorobutyloxy- carbonyl, l-chloro-2-propyloxycarbonyl, l,3-dichloro-2-propyloxycarbonyl, 2,2-dichloroethyloxycarbonyl, 2,2,2-trifluoroethyloxycarbonyl, and 2,2,2-tri- chloroethyloxycarbonyl; (C₃-C₁₀ cycloalkoxy)carbonyl may include cyclo- propyloxycarbonyl, cyclobutyloxycarbonyl, cyclop entyloxycarbonyl, and cyclohexyloxycarbonyl; (C₃-C_ι0 halocycloalkoxy)carbonyl may include 2-fluorocyclopentyloxycarbonyl and 3,4-dichlorocyclohexyloxycarbonyl; carboxy C_ι-C₅ alkyl may include carboxymethyl, 2-carboxyethyl, and 1-carboxyethyl; (hydroxy d-C₅ alkoxy)carbonyl C_ι-C₅ alkyl may include hydroxymethoxycarbonylmethyl, 2-(hydroxymethoxycarbonyl)ethyl, 2-hydroxyethoxycarbonylmethyl, 2-(2-hydroxyethoxycarbonyl)ethyl, and l-(2-hydroxyethoxycarbonyl)ethyl; (C_J-C_IQ alkoxy)carbonyl C_ι-C₅ alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxy- carbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylm ethyl, isoamyl- oxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, and 1-isoamyloxycarbonylethyl; (C_ι-C_ι0 halo- alkoxy)carbonyl C_ι-C₅ alkyl may include chloromethyloxycarbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloropropyloxycarbonylmethyl, 3-chloro- butyloxycarbonylmethyl, l-chloro-2-propyloxycarbonylmethyl, 1,3-dichloro- 2-propyloxycarbonylmethyl, 2,2-dichloroethyloxycarbonylmethyl, 2,2,2-tri- fluoroethyloxycarbonylmethyl, and 2,2,2-trichloroethyloxycarbonylethyl; (C₃-C₁₀ cycloalkoxy)carbonyl C_ι-C₅ alkyl may include cyclopropyloxycarbonyl- methyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1 -cyclop en tyloxy- carbonylethyl, and 1-cyclohexyloxycarbonylethyl; (C₃-C_ι0 halocycloalkoxy)- carbonyl C_ι-C₅ alkyl may include 2-fluorocyclopentyloxycarbonylmethyl and 2-(3,4-dichlorocyclohexyloxycarbonyl)ethyl; aminocarbonyl Ci-Cg alkyl may include aminocarbonylmethyl, 1-aminocarbonylethyl, and 2-aminocarbonylethyl; (Ci-Cg alkylamino)carbonyl C_ι-C₆ alkyl may include methylamino- carbonylmethyl, ethylaminocarbonylmethyl, 1-methylaminocarbonylethyl, l-(ethylaminocarbonyl)ethyl, l-(propylaminocarbonyl)ethyl, 2-methylamino- carbonylethyl, and 2-(ethylaminocarbonyl)ethyl; C_ι-C₆ alkoxy C_j-C₈ alkyl may include methoxymethyl, 1-methoxyethyl, and ethoxymethyl; Ci-Cg haloalkoxy Cj-Cg alkyl may include 2,2,2-trifTuoroethoxymethyl; mercapto C_ι-C₆ alkyl may include mercaptomethyl, 1-mercaptoethyl, and 2-mercaptoethyl; {(Cj-Cg alkoxy) Cj-Cg alkoxy} carbonyl C C₆ alkyl may include methoxy- methoxycarbonylmethyl, 2-(methoxymethoxycarbonyl)ethyl, l-(methoxy- methoxycarbonyl)ethyl, l-(ethoxymethoxycarbonyl)ethyl, l-(propoxy- methoxycarbonyl)ethyl, l-(isopropoxymethoxycarbonyl)ethyl, l-(l-methoxy- ethoxycarbonyl)ethyl, l-(l-ethoxyethoxycarbonyl)ethyl, 1- (2 -methoxy ethoxy- carbonyl)ethyl, l-(2-ethoxyethoxycarbonyl)ethyl, l-(2-propoxyethoxy- carbonyl) ethyl, l-(2-isopropoxyethoxycarbonyl)ethyl, 2-(2-methoxyethoxy- carbonyl)ethyl, 2-(2-ethoxyethoxycarbonyl)ethyl, 2-(2-propoxyethoxy- carbonyl)ethyl, and 2-(2-isopropoxyethoxycarbonyl)ethyl; Cj-Cg alkylthio Ci-Cg alkyl may include methylthiomethyl, 1-methylthioethyl, and ethyl- thiomethyl; C,-Cg haloalkylthio C_ι-C₆ alkyl may include 2,2,2-trifluoroethyl- thiomethyl; cyano C_ι-C₄ alkyl may include cyanomethyl, cyanoethyl, and 1-methylcyanoethyl; optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-methoxyphenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxy- carbonylphenyl, 3-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichloro- phenyl, and 2,5-dichlorophenyl; (optionally substituted phenyl) Cι-C₃ alkyl may include benzyl, phenethyl, 1-methylbenzyl, 2-chlorobenzyl, 3-chloro- benzyl, 4-chlorobenzyl, 2-methoxybenzyl, 3-methoxybenzyl, and 4-methoxybenzyl; and optionally substituted phenylcarbonyl may include benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2,3-dichlorobenzoyl, 2,4- dichlorobenzoyl, 2,5-dichlorobenzoyl, 2,6-dichlorobenzoyl, and 3,4-dichloro- benzoyl.

For the groups represented by R¹³, R⁴³, or R⁷³, Cι-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, t-butyl, isopentyl, n-hexyl, and n-octyl; d-C₁₀ haloalkyl may include 2-fluoroethyl, 2,2,2-trifluoroethyl, 5-chloro-n-pentyl, and 1-bromoheptyl; C₃-C_ι0 alkenyl may include vinyl, allyl, l-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C₃-C_ι0 haloalkenyl may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl; C₃-C₁₀ alkynyl may include propargyl, l-methyl-2- propynyl, 2-butynyl, 3-butynyl, and l, l-dimethyl-2-propynyl; C₃-C₁₀ halo- alkynyl may include 3-iodo-2-propynyl and 3-bromo-2-propynyl; C₃-C₈ cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 4,4-di- methylcyclohexyl; C₃-C₈ halocycloalkyl may include 2-fluorocyclopentyl and 3,4-dichlorocyclohexyl; tetrahydrofuranyl may include 2 -tetrahydrofuranyl and 3-tetrahydrofuranyl; tetrahydropyranyl may include 2-tetrahydro- pyranyl and 3-tetrahydropyranyl; carboxy d- alkyl may include carboxymethyl, 2-carboxyethyl, and 1-carboxyethyl; (C₃-C₈ cycloalkoxy)carbonyl Ci-Cg alkyl may include cyclopropyloxycarbonylmethyl, cyclobut loxy- carbonylmethyl, cyclop en tyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, 1-cyclohexyloxycarbonyl ethyl, 2-cyclobutyloxycarbonylethyl, 2-cyclopentyl- oxycarbonylethyl, and 2-cyclohexyloxycarbonylethyl; (C₃-C₈ alkenyloxy)- carbonyl d- ₆ alkyl may include aUyloxycarbonylmethyl, l-methyl-2-prope- nyloxycarbonylmethyl, 2-methyl-2-propenyloxycarbonylmethyl, 2-butenyl- oxycarbonylmethyl, 1-allyloxycarbonylethyl, l-(2-methyl-2-propenyloxy- carbonyl)ethyl, 2-allyloxycarbonylethyl, and 2-(2-methyl-2-propenyloxy- carbonyl)ethyl; (C₃-C₈ alkynyloxy)carbonyl C_ι-C₆ alkyl may include propar- gyloxycarbonylmethyl, l-methyl-2-propynyloxycarbonylmethyl, 1-propargyl- oxycarbonylethyl, l-(l-methyl-2-propynyloxycarbonyl)ethyl, 2-propargyloxy- carbonylethyl, and 2-(l-methyl-2-propynyloxycarbonyl)ethyl; tetrahydro- furanyloxycarbonyl C_ι-C₆ alkyl may include 2-tetrahydrofuranyloxy- carbonylmethyl, 3-tetrahydrofuranyloxycarbonylmethyl, l-(2-tetrahydro- furanyloxycarbonyl) ethyl, l-(3-tetrahydrofuranyloxycarbonyl)ethyl, 2-(2- tetrahydrofuranyloxycarbonyl)ethyl, and 2-(3-tetrahydrofuranyloxy- carbonyl)ethyl; tetrahydropyranyloxycarbonyl Ci-Cg alkyl may include 2-tetrahydropyranyloxycarbonylmethyl, 3-tetrahydropyranyloxycarbonyl- methyl, l-(2-tetrahydropyranyloxycarbonyl)ethyl, l-(3-tetrah dropyranyl- oxycarbonyl)ethyl, 2-(2-tetrahydropyranyloxycarbonyl)ethyl, and 2-(3-tetra- hydropyranyloxycarbonyl)ethyl; (C_ι-C₅ alkoxy)carbonyl Ci-C₅ alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxy- carbonylmethyl, t-butoxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxy- carbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxy- carbonylethyl, 1-isobutoxycarbonylethyl, and 1-t-butoxycarbonylethyl; and (d- haloalkoxy)carbonyl d-C₅ alkyl may include chloromethyloxycarbonyl, 2-fluoroethyloxycarbonyl, 2-chloropropyloxycarbonyl, 3-chlorobutyloxy- carbonyl, l-chloro-2-propyloxycarbonyl, l,3-dichloro-2-propyloxycarbonyl, 2,2-dichloroethyloxycarbonyl, 2,2,2-trifluoroethyloxycarbonyl, and 2,2,2-tri- chloroethyloxycarbonyl.

For the groups represented by R¹⁴, R⁴⁴, or R⁷⁴, C_ι-C₅ alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and t-butyl; d- haloalkyl may include fluoromethyl, chloromethyl, bromomethyl, trifluoro- methyl, chlorodifluoromethyl, difluoromethyl, and pentafluoromethyl; C₃-C₆ cycloalkyl may include cyclopropyl, cyclopentyl, and 1-methylcyclopropyl; and C₃-C₆ halocycloalkyl may include 2,2-difluorocyclopropyl and 3-chloro- cyclopentyl. For the groups represented by R¹⁵, R⁴⁵, or R⁷⁵, C_ι-C_ι0 alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, and n-hexyl; and d-C₁₀ haloalkyl may include chloromethyl, trifluoromethyl, chloroethyl, 2,2,2-trifluoroethyl, and 3-chlorohexyl.

For the elements or groups represented by R¹⁶, R⁴⁶, or R⁷⁶, halogen may include fluorine, chlorine, and bromine; and C_rC₃ alkyl may include methyl, ethyl, propyl, and isopropyl.

For the groups represented by R¹⁷, R⁴⁷, or R⁷⁷, d-C_B alkyl may include methyl, ethyl, propyl, isopropyl, and n-butyl.

For the groups represented by R¹⁸, R⁴⁸, or R⁷⁸, C_rC₄ alkyl may include methyl, ethyl, isopropyl, and n-butyl; C_ι-C₄ haloalkyl may include chloromethyl, 2 -chloroethyl, trifluoromethyl, and tetrafluoroethyl, chlorodifluoromethyl; C₃-C₅ cycloalkyl may include cyclopropyl, cyclopentyl, and 1-methylcyclopropyl; and C₃-C₅ halocycloalkyl may include 2,2-difluorocyclopropyl and 3-chlorocyclopentyl. For the groups represented by R¹⁹, R⁴⁹, or R⁷⁹, d-C₁₀ alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, and n-hexyl; d-C₁₀ haloalkyl may include 2-chloroethyl, 2,2,2-trifluoroethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 5-chloro-n-amyl, and 7-bromoheptyl; C₃-C₆ cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 1-methylcyclopropyl; C₃-C₆ halocycloalkyl may include 2,2-difluorocyclopropyl and 3-chlorocyclopentyl; C₃-C_ι0 cycloalkyl d-C₃ alkyl may include cyclopropylmethyl, cyclopentylmethyl, and cyclohexylethyl; C₃-C_ι0 halocyclo- alkyl d-C₃ alkyl may include 2-fluorocyclopentylmethyl and 3,4-dichloro- cyclohexylethyl; C₃-C₅ alkenyl may include allyl, l-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C₃-C₅ haloalkenyl may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl; C₃-C₅ alkynyl may include propargyl, l-methyl-2-propynyl, 2-butynyl, 3-butynyl, and l,l-dimethyl-2-propynyl; C₃-C₅ haloalkynyl may include 3-iodo-2-propynyl and 3-bromo-2-propynyl; carboxy d-C₃ alkyl may include carboxymethyl, 2-carboxyethyl, and 1-carboxyethyl; (C_ι-C₅ alkoxy)carbonyl Cι-C₃ alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C_ι-C₅ haloalkoxy)carbonyl C_ι-C₃ alkyl may include chloromethyloxy- carbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloropropyloxy- carbonylmethyl, 3-chlorobutyloxycarbonylmethyl, l-chloro-2-propyloxy- carbonylmethyl, l,3-dichloro-2-propyloxycarbonylmethyl, 2,2-dichloroethyl- oxycarbonylmethyl, 2,2,2-trifluoroethyloxycarbonylmethyl, and 2,2,2-tri- chloroethyloxycarbonylethyl; optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluorophenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-tri- fluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, and 2,5-di- chlorophenyl; and (optionally substituted phenyl) d-C₃ alkyl may include benzyl, phenethyl, 1-methylbenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chloro- benzyl, 2-methoxybenzyl, 3-methoxybenzyl, and 4-methoxybenzyl.

For the groups represented by R²⁰, R⁵⁰, or R⁸⁰, Cι-C_ε alkyl may include methyl, ethyl, isopropyl, n-butyl, t-butyl, n-pentyl, and isopentyl; Cι-C₅ haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 3-chloro-n-propyl, 2,2,2- trifluoroethyl, and 5-chloro-n-pentyl; C₃-C₆ cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 1-methylcyclopropyl; and C₃-C₆ halocycloalkyl may include 2,2-difluorocyclopropyl, 3-chlorocyclopentyl, and 4,4-difluorocyclohexyl.

For the elements represented by M, alkali metals may include lithium, sodium, and potassium.

For the groups represented by R³⁴, d-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, isopentyl, and n-octyl; d-C₁₀ haloalkyl may include 2-fluoroethyl, 2,2,2-trifluoroethyl, 5-chloro-n-pentyl, and 7-bromoheptyl; and optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-methylphenyl, 4-tri- fluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-tri- fluoromethylphenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-trifluoro- methoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, and 2,5-dichloro- phenyl.

For the groups represented by R²¹, C_ι-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, isopentyl, and n-octyl; C_ι-C₁₀ haloalkyl may include 2-fluoroethyl, 2,2,2-trifluoroethyl, 5-chloro-n-pentyl, and 1-bromoheptyl; C₃-C₈ cycloalkyl may include cyclopropyl, cyclopentyl, cyclohexyl, and 4,4-di- methylcyclohexyl; C₃-C₈ halocycloalkyl may include 2-fluorocyclopentyl, 3,4- dichlorocyclohexyl; and optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxy- carbonylphenyl, 3-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichloro- phenyl, and 2,5-dichlorophenyl.

For the groups represented by R²², C_ι-C_ι0 alkyl may include methyl, ethyl, isopropyl, n-butyl, isopentyl, and n-octyl; d-C₁₀ haloalkyl may include chloromethyl, trichloromethyl, trifluoromethyl, 2 -chloroethyl, 2-fluoroethyl, 3-chloropropyl, 2,2,2-trifluoroethyl, 5-chloro-n-pentyl, and 7-bromoheptyl; C₃-C₈ cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, and 4,4-dimethylcyclohexyl; C₃-C₈ halocycloalkyl may include 2,2-difluorocyclopropyl, 3-chlorocyclopentyl, and 4,4-difluorocyclo- hexyl; and optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-tri- fluoromethylphenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-trifluoro- methoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, and 2,5-dichlorophenyl.

For the groups represented by R²³, C_ι-C₅ alkyl may include methyl, ethyl, n-propyl, isopropyl, and butyl.

For the groups represented by R²⁴, C_ι-C_ε alkyl may include methyl, ethyl, n-propyl, isopropyl, and butyl; d-C₅ haloalkyl may include 2-chloro- ethyl, tetrafluoroethyl, 2-fluoroethyl, 3-chloro-n-propyl, and 2-chloro-2- methylpropyl; and optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 3,4-dimethylphenyl, 2,4-dimethylphenyl, and 2 , 5-dimethylphenyl.

For the groups represented by R²⁵, d-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, isopentyl, n-octyl, and 4,4-dimethyl-n-hexyl; d-C₁₀ haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 3-chloron-propyl, 2,2,2- trifluoroethyl, 5-chloro-n-pentyl, and 1-bromoheptyl; C_ι-C₅ alkylsulfonyl may include methylsulfonyl and ethylsulfonyl; C₃-C_ι0 cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 4,4-di- methylcyclohexyl, and 2,2,4,4-tetramethylcyclohexyl; C₃-C_ι0 halocycloalkyl may include 2,2-difluorocyclopropyl, 3-chlorocyclopentyl, and 4,4-difluoro- cyclohexyl; carboxy C C₃ alkyl may include carboxymethyl, 2-carboxyethyl, and 1-carboxyethyl; (C_ι-C_ε alkoxy)carbonyl Cι-C₃ alkyl may include meth oxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, and 1-t-butoxycarbonylethyl; and optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-methylphenyl, 4-trifluoromethyl- phenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3 -trifluoromethyl phenyl, 3-bromophenyl, 3-methoxycarbonylphenyl, 3-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 3,4-di- methylphenyl, 2,4-dimethylphenyl, and 2, 5-dimethylphenyl.

For the groups represented by R²⁶, d-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, t-butyl, n-pentyl, isopentyl, n-octyl, and 4,4-dimethyl-n-hexyl; and Ci-Ci_o haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 3-chloro-n-propyl, 2,2,2-trifluoroethyl, 5-chloro-n-pentyl, and 1-bromoheptyl. For the groups represented by R²⁷, C_rC_ε alkyl may include methyl, ethyl, isopropyl, n-butyl, t-butyl, n-pentyl, and isopentyl; and d-C_ε haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 3-chloro-n-propyl, 2,2,2-trifluoroethyl, and 5-chloro-n-pentyl. For the groups represented by R²⁸, d-C₁₀ alkyl may include methyl, ethyl, isopropyl, n-butyl, t-butyl, n-pentyl, isopentyl, n-octyl, and 4,4-di- methyl-n-hexyl; and d-d₀ haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 3-chloron-propyl, 2,2,2-trifluoroethyl, 5-chloro-n-pentyl, and 2-chloro- 1 , 1 ,4,4-tetramethylhexyl. For the groups represented by R²⁹, d-C₁₀ alkyl may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, and n-octyl.

For the groups represented by R³⁰, d-C₁₀ alkyl may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, and n-octyl; d-C₁₀ haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 3-chloro-n-propyl, 2,2,2-trifluoroethyl, and 5-chloro-n-pentyl; C₃-C_ι0 cycloalkyl may include cyclopropyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 4,4-dimethylcyclohexyl, and 2,2,4,4-tetramethylcyclohexyl; C₃-C_ι0 halocycloalkyl may include 2,2-difluorocyclopropyl, 3-chlorocyclopentyl, and 4,4-di- fluorocyclohexyl; and optionally substituted phenyl may include phenyl, 2-chlorophenyl, 2-nitrophenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 4-chlorophenyl, 4-nitrophenyl, 4-isopropoxyphenyl, 4-fluorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 3-nitrophenyl, 3-methoxyphenyl, 3-methylphenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-methoxy- carbonylphenyl, 3-trifluoromethoxyphenyl, 3,4-dichlorophenyl, 2,4-dichloro- phenyl, 2,5-dichlorophenyl, 3,4-dimethylphenyl, 2,4-dimethylphenyl, and 2 , 5-dimethylphenyl.

For the groups represented by R²⁰⁰, C_ι-C₃ alkyl may include methyl, ethyl, propyl, and isopropyl; C -C₃ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, and 1,1-difluoroethyl; C₃-C₆ alkenyl may include allyl, l-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; and C₃-C₆ alkynyl may include propargyl, l-methyl-2-propynyl, 2-butynyl, 3-butynyl, and l,l-dimethyl-2- propynyl.

For the groups represented by R³⁰⁰, C_ι-C₃ haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, pentafluoroethyl, and 1,1-difluoroethyl. For the groups represented by R²⁰⁰ and R³⁰⁰ which are combined at their ends, optionally fluorine-substituted trimethylene may include trimethylene, 1, 1,2-trifluorotrimethylene, and 2,3,3-trifluorotrimethylene; and optionally fluorine-substituted tetramethylene may include tetramethylene. In the present compounds, the substituent groups preferred may include oxygen for X and Y; hydrogen or C_ι-C₃ alkyl for R¹; C_rC₃ alkyl (more preferably, methyl) or amino for R²; C_ι-C₃ haloalkyl (more preferably trifluoromethyl) for R³; hydrogen for R⁴; hydrogen or halogen (more preferably, chlorine) for R⁵; hydrogen or halogen (more preferably, chlorine) for R⁶; halogen (more preferably, chlorine) or NO₂ for R⁷; hydrogen, C_ι-Cι₀ alkoxy (more preferably, methoxy or isopropoxy), C₃-C₈ alkenyloxy (more preferably, allyloxy), C₃-C₈ alkynyloxy (more preferably, propargyloxy), (d-C_ι0 alkoxy)- carbonyl d-C₅ alkyloxy (more preferably, l-(methoxycarbonyl)ethoxy or l-(ethoxycarbonyl)ethoxy), C_x-C₁₀ alkylamino (more preferably, ethylamino or isopropylamino), C_ι-C₁₀ alkyl (Ci-Cj_o alkyl)amino (more preferably, diethylamino), 2,2-di(C_ι-C_ε alkyl)hydrazino (more preferably, 2,2-dimethyl- hydrazino), or C_ι-C₆ alkoxy C_ι-C₆ alkylamino for R⁸. When R⁷ is chlorine, compounds with l-(d-C_ι0 alkoxy)carbonylethoxy (more preferably, l-(methoxycarbonyl)ethoxy or l-(ethoxycarbonyl)ethoxy) for R⁸ are more preferred. When R⁷ is NO₂, compounds with d-C₁₀ alkoxy (more preferably, methoxy or isopropoxy) for R⁸ are more preferred. Compounds with a combination of the above preferred substituent groups are more preferred.

For the present compounds, there may exist geometrical isomers based on the presence of a double bond, or optical isomers and diastereomers based on the presence of at least one asymmetric carbon atom, and all of these isomers and their mixtures are also included within the scope of the present invention.

The following will describe the producing processes for the present compounds. The present compounds can be produced, for example, by the producing processes described in following Producing Processes 1 to 11. Producing Process 1

[1-1] [1-3] wherein R¹, X, Y, Z, and Q are as defined above; R²⁰¹ is optionally fluorine- substituted C C₃ alkyl, C₃-C₆ alkenyl, or C₃-C₆ alkynyl; D is chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy; and R³⁰¹ is d-C₃ alkyl or C_ι-C₃ haloalkyl.

The present compound [1-3] can be produced by reacting compounds

[1-1] and [1-2] in the presence of a base. The reaction is usually carried out in a solvent; however, it may also be carried out without any solvent. The reaction temperature is usually in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usually in the range of a moment to 48 hours.

The amount of compound [1-2] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [1-1].

The amount of base to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [1-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylani1ine, N,N-diethylaniline, triethylamine, and (hϊsopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, lithium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium hydroxide, potassium hydroxide, and lithium hydroxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [1-3]. The compound may be purified by a technique such as chromatography or recrystalliz ation .

Producing Process 2

[1-1] [2-2]

wherein R¹, R³⁰¹, X, Y, Z, and Q are as defined above; and W is nitro- substituted phenyloxy {e.g., 2,4-dinitrophenyloxy, 2,4,6-trinitrophenyloxy), optionally substituted phenylsulfonyloxy {e.g., 2,4,6-trimethylphenyl- sulfόnyloxy), or sulfonyloxy.

The present compound [2-2] can be produced by reacting compounds [1-1] and [2-1] in the presence of a base. The reaction is usually carried out in a solvent. The reaction temperature is usually in the range of -20°C to 200°C, preferably 20°C to 100°C. The reaction time is usually in the range of a moment to 72 hours.

The amount of compound [2-1] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.5 to 1.2 moles, for 1 mole of compound [1-1].

The amount of base to be used in the reaction is usually in the range of 0.1 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [1-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and l,4-diazabicyclo[2.2.2]octane; and inorganic bases such as sodium carbonate, potassium carbonate, lithium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium hydroxide, potassium hydroxide, and lithium hydroxide. The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitriles such as acetonitrile and isobutyronitrile; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniline, N,N- diethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; water; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [2-2]. The compound may be purified by a technique such as chromatography or recrystallization. Producing Process 3

[3-4] wherein R¹, R³⁰¹, D, X, Y, Z, and Q are as defined above; and R⁶³ and R⁶⁴ are the same or different and independently optionally fluorine-substituted d-d alkyl. 1) Step of producing compound [3-2] from compound [2-2]

The present compound [3-2] can be produced by reacting compounds [2-2] and [3-1] in the presence of a base.

The reaction is usually carried out in a solvent; however, it may also be carried out without any solvent. The reaction temperature is usually in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usually in the range of a moment to 48 hours.

The amount of compound [3-1] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [2-2]. The amount of base to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [2-2].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and dnsopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, hthium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium hydroxide, potassium hydroxide, and lithium hydroxide.

The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as mtromethane and nitrobenzene; acid amides such as N,N-dimethyl- formamide and acetamide; tertiary amines such as pyridine, N,N-dimethyl- aniline, N,N-diethylaniline, triethylamine, and clfisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [3-2]. The compound may be purified by a technique such as chromatography or recrystallization.

2) Step of producing compound [3-4] from compound [3-2]

The present compound [3-4] can be produced by reacting compounds [3-2] and [3-3] in the presence of a base.

The amount of compound [3-3] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [3-2]. The amount of base to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [3-2].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylani1ine, N,N-diethylaniline, triethylamine, and diisopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, lithium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium hydroxide, potassium hydroxide, and hthium hydroxide.

The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethyl- formamide and acetamide; tertiary amines such as pyridine, N,N-dimethyl- aniline, N,N-diethylaniline, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [3-4]. The compound may be purified by a technique such as chromatography or recrystallization.

Producing Process 4

[2-2] _[4__2]

wherein R¹, R³⁰¹, R⁶³, R⁶⁴, X, Y, Z, and Q are as defined above.

The present compound [4-2] can be produced by reacting compounds [2-2] and [4-1]. The reaction is usually carried out in a solvent or without any solvent.

The reaction temperature is usually in the range of -20°C to 200°C, preferably 0°C to 130°C. The reaction time is usually in the range of a moment to 48 hours.

The amount of compound [4-1] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [2-2].

The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; and mixtures thereof.

The reaction may be carried out in a shortened reaction time by the addition of a catalyst. The amount of catalyst is usually in the range of 0.001 mole to an excess for 1 mole of compound [2-2]. The catalyst may include Lewis acids such as titanium tetrachloride and boron trifluoride- diethyl ether complex; organic acids such as benzenesulfonic acid and p-toluenesulfonic acid; organic bases such as pyridine, 4-dimethylamino- pyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; and inorganic bases such as sodium carbonate and potassium carbonate.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [4-2]. The compound may be purified by a technique such as chromatography or recrystallization.

Producing Process 5

[5-1] [5-3]

wherein R¹, X, Y, Z, and Q are as defined above; V is fluorine, chlorine, bromine, or iodine; R²⁰³ is C C₃ alkyl, C_ι-C₃ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, or N(R⁶¹)R⁶² wherein R⁶¹ and R⁶² are as defined above; R³⁰³ is C_x-C₃ alkyl or C_ι-C₃ haloalkyl; or R²⁰³ and R³⁰³ may be combined at their ends to form optionally fluorine-substituted trimethylene or optionally fluorine- substituted tetramethylene. The present compound [5-3] can be produced by reacting compounds

[5-1] and [5-2] in the presence of a base.

The reaction is usually carried out in a solvent. The reaction temperature is usually in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usually in the range of a moment to 48 hours. The amount of compound [5-2] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [5-1].

The amount of base to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [5-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, hthium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium hydroxide, potassium hydroxide, and hthium hydroxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof. The reaction may be carried out in a shortened reaction time by the addition of a catalyst. The amount of catalyst is usually in the range of 0.001 mole to an excess for 1 mole of compound [5-1]. The catalyst may include fluorides such as potassium fluoride.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [5-3]. The compound may be purified by a technique such as chromatography or recrystallization.

Producing Process 6

wherein R¹, X, Z, and Q are as defined above; R³² is C_ι-C₆ alkyl {e.g., methyl. ethyl) or phenyl; R²⁰² is -d alkyl, C d haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, or N(R⁶¹)R⁶² wherein R⁶¹ and R⁶² are as defined above; and R³⁰² is -d alkyl or C_rC₃ haloalkyl.

The present compound [6-3] can be produced by reacting compounds [6-1] and [6-2] in the presence of a base. The reaction is usually carried out in a solvent. The reaction temperature is usually in the range of -20°C to 250°C, preferably 0°C to 150°C. The reaction time is usually in the range of a moment to 72 hours.

The amount of compound [6-2] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [6-1].

The amount of base to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [6-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; inorganic bases such as sodium carbonate, potassium carbonate, hthium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide; and metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aliphatic hydrocarbons such as hexane, heptane, octane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as mtromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniiine, N,N-diethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [6-3]. The compound may be purified by a technique such as chromatography or recrystallization.

Producing Process 7

wherein R¹, R², R³, X, Z, and Q are as defined above. The present compound [7-1] can be produced by reacting compound

[7-2] with a sulfurizing agent.

The reaction is usually carried out in a solvent. The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of a moment to 48 hours. The amount of sulfurizing agent to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [7-2].

The sulfurizing agent may include lawson reagent. The solvent may include aromatic hydrocarbons such as toluene and xylene.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are collected by filtration; or the reaction mixture is poured into water, followed by extraction with an organic solvent and concentration, thus obtaining compound [7-1]. The compound may be purified by a technique such as chromatography or recrystalliz ation . Producing Process 8

[8-1] [8-3]

wherein R¹, R²⁰³, R³⁰³, X, Y, Q, and V are as defined above.

The present compound [8-3] can be produced by reacting compounds [8-1] and [8-2] in the presence of a base. The reaction is usually carried out in a solvent. The reaction temperature is usually in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usually in the range of a moment to 24 hours.

The amount of compound [8-2] to be used in the reaction is usually in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [8-1].

The amount of base to be used in the reaction is usually in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [8-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and (fiisopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide. The solvent may include ahphatic hydrocarbons such as hexane, heptane, octane, and Hgroin; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; aHphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2- dichloroethane, and 1,2,3-trichloropropane; aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitrobenzene; acid amides such as N,N-dixnethyKormamide; sulfur compounds such as dimethyl- sulfoxide and sulforane; water; and mixtures thereof.

The reaction may be carried out in a shortened reaction time by the addition of a catalyst. The amount of catalyst is usuaUy in the range of

0.001 mole to an excess for 1 mole of compound [8-1]. The catalyst may include phase transfer catalysts such as tetrabutylammonium chloride and tetrabutylammonium bromide.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [8-3]. The compound may be purified by a technique such as chromatography or recrystalHzation.

Producing Process 9

[5-1] [5-3]

wherein R¹, R²⁰³, R³⁰³, X, Y, Z, and Q are as defined above; and L is bismuth.

The present compound [5-3] can be produced by reacting compounds [5-1] and [9-2] in the presence of a catalyst and a peracid. The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 48 hours.

The amount of compound [9-2] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [5-1].

The amount of catalyst to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [5-1].

The amount of peracid to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [5-1].

The catalyst may include organic copper compounds such as copper acetate.

The peracid may include peracetic acid, m-chloroperbenzoic acid, t-butyl hydroperoxide, and hydrogen peroxide.

The solvent may include aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, dusopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitriles such as acetonitrile and isobutyronitrile; aHphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; aHphatic carbox- yHc acids such as acetic acid; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [5-3]. The compound may be purified by a technique such as chromatography or recrystaUization. The present compounds may also be produced by converting the substituents on the optionaUy substituted phenyl group represented by Q according to any of the methods known in the field of organic synthesis, for example, as in the producing processes described in the foUowing Producing Processes 10 and 11. Producing Process 10 '

[5-1] [10-2]

[10-4] wherein R¹, R²⁰³, R³⁰³, V, X, Y, Z, and Q are as defined above; and R⁶⁰ is OR⁹, SR¹⁰, N(R^π)R¹², NR^πN(R¹⁰)R¹², or NR^uOR⁹, wherein R⁹, R¹⁰, R¹¹, and R¹² are as defined above.

1) Step of producing compound [10-2] from compound [5-1] The present compound [10-2] can be produced by reacting compounds

[5-1] and [10-1] in the presence of a base.

The reaction is usuaHy carried out in a solvent; however, it may also be carried out without any solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 48 hours.

The amount of compound [10-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [5-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [5-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniHne, N,N-diethylaniline, triethylamine, and dusopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide. The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as mtromethane and nitrobenzene; acid amides such as N,N-dimethyl- formamide and acetamide; tertiary amines such as pyridine, N,N-dimethyl- aniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

The reaction may be carried out in a shortened reaction time by the addition of a catalyst. The amount of catalyst is usuaUy in the range of 0.001 mole to an excess for 1 mole of compound [5-1]. The catalyst may include fluorides such as potassium fluoride. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [10-2]. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [10-4] from compound [10-2] The present compound [10-4] can be produced by reacting compounds [10-2] and [10-3].

The reaction is usuaUy carried out in a solvent; however, it may also be carried out without any solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 48 hours.

The compound [10-3] to be used in the reaction may also be available as its inorganic salt {e.g., hydrochloride salt, sulfate). The amount thereof is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 2.2 moles, for 1 mole of compound [10-2].

The reaction may be carried out in a shortened reaction time by the addition of a base. The amount of base is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 4.4 equivalents, for 1 mole of compound [10-2]. The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dim ethylanih^' e, N,N-diethylaniHne, triethylamine, and dnsopropylethylamine; metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium t-butoxide; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide.

The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as mtromethane and nitrobenzene; acid amides such as N,N-dimethyl- formamide and acetamide; tertiary amines such as pyridine, N,N-dimethyl- aniline, N,N-diethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [10-4]. The compound may be purified by a technique such as chromatography or recrystaUization.

Producing Process 11

wherein R¹, R²⁰³, R³⁰³, L, D, X, Y, and Z are as defined above; U is a silyl-type protecting group such as t-butyldimethylsilyl, phenyldimethylsUyl, and tri- isopropylsilyl; Q¹ is optionaUy substituted phenylene; and R³⁵ is one of the substituents represented by R⁹, other than hydrogen.

1) Step of producing compound [11-2] from compound [5-1] The present compound [11-2] can be produced by reacting compounds [5-1] and [11-1] in the presence of a catalyst and a peracid.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 48 hours. The amount of compound [11-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [5-1].

The catalyst may include organic copper compounds such as copper acetate.

The solvent may include aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydro- carbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, dnsopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitriles such as acetonitrile and isobutyronitrile; aHphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; aHphatic carbox- yhc acids such as acetic acid; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [11-2]. The compound may be purified by a technique such as chromatography or recrystaUiz ation .

2) Step of producing compound [11-3] from compound [11-2] The compound [11-3] can be produced by deprotecting compound [11-2] with potassium fluoride or potassium fluoride/hydrogen bromide in a solvent such as N,N-dimethylformamide, according to the method described in "Protective Groups in Organic Synthesis" (A Wfley-Interscience PubHca- tion).

3) Step of producing compound [11-4] from compound [11-3] The present compound [11-4] can be produced by reacting compounds

[11-3] and [11-5] in the presence of a base.

The amount of compound [11-5] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [11-3].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [11-3].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylani1ine, N,N-diethylaniHne, triethylamine, and dusopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide. The solvent may include ketones such as acetone and methyl isobutyl ketone; aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N.N-dimethylaniline, N,N-diethylaniline, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [11-4]. The compound may be purified by a technique such as chromatography or recrystalHzation.

The foUowing wiU describe the producing processes for the present intermediates A as the intermediates useful for the production of the present compounds. The present intermediates A can be produced, for example, by the producing processes described in the foUowing Producing Processes Al to A4. Producing Process Al

wherein R¹, R³⁰¹, R³², X, Z, and Q are as defined above.

The present intermediate A [Al-2] can be produced by reacting compounds [6-1] and [Al-1] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to

130°C. The reaction time is usuaUy in the range of a moment to 72 hours.

The amount of compound [Al-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [6-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [6-1]. The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylanilin e, N,N-diethylaniline, triethylamine, and dusopropylethylamine; inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide; and metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N.N-dimethylaniHne, N,N-diethylaniHne, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or acid is poured into the reaction mixture and the deposited crystals are coUected by filtration; or acid is poured into the reaction mixture, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Al-2]. The acid to be added may include hydrochloric acid, acetic acid, trifluoro- acetic acid, p-toluenesulfonic acid, and aqueous solutions thereof. The compound may be purified by a technique such as chromatography or recrystalHzation.

Producing Process A2

[A2-3] wherein R\ R³⁰¹, R³², X, Z, and Q are as defined above.

The present intermediate A [Al-2] can be produced by reacting compound [A2-1] and compound [A2-2] or [A2-3] in the presence of a base. The reaction is usuaUy carried out in a solvent. The reaction temperature is usually in the range of -20°C to 200°C, preferably 0°C to 130°C. The reaction time is usuaUy in the range of a moment to 72 hours.

The amount of compound [A2-2] or [A2-3] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [A2-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [A2-1]. The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-<Hethylaniline, triethylamine, and dusopropylethylamine; inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide; and metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, dusopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniHne, N,N-cuethylaniline, triethylamine, and diisopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or acid is poured into the reaction mixture and the deposited crystals are coUected by filtration; or acid is poured into the reaction mixture, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Al-2].

The acid to be added may include hydrochloric acid, acetic acid, trifluoro- acetic acid, p-toluenesulfonic acid, and aqueous solutions thereof. The compound may be purified by a technique such as chromatography or recryst aUiz ation . Producing Process A3

[A3-1] [A3-2] [Al-2] wherein R¹, R³⁰¹, X, Z, and Q are as defined above.

1) Step of producing compound [A3-2] from compound [A3-1]

The compound [A3-2] can be produced by reacting compound [A3-1] with ammonia or ammonium acetate in the presence of an acid.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to 150°C. The reaction time is usuaUy in the range of a moment to 72 hours.

The amount of ammonia or ammonium acetate to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [A3-1].

The amount of acid to be used in the reaction is usuaUy in the range of 0.001 to 1 equivalent, relative to compound [A3-1].

The acid may include organic acids such as acetic acid. The solvent may include alcohols such as ethanol. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [A3-2]. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [Al-2] from compound [A3-2] The present intermediate A [Al-2] can be produced by reacting compound [A3-2] with a carbonylating agent or a thiocarbonylating agent in the presence of a base.

In the compound [Al-2], when a carbonylating agent is used, X is O; or when a thiocarbonylating agent is used, X is S. The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to 150°C, preferably 10°C to 60°C. The reaction time is usuaUy in the range of a moment to 48 hours.

The amount of carbonylating agent or thiocarbonylating agent to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, prefer- ably 0.8 to 1.2 moles, relative to compound [A3-2].

The amount of base to be used in the reaction is usuaUy in the range of 1.0 equivalent to an excess, preferably 1.8 to 2.2 equivalents, relative to compound [A3-2].

The carbonylating agent may include phosgene, diphosgene, triphosgene, and l,l'-carbonyldumidazole, and the thiocarbonylating agent may include thiophosgene and l.l'-thiocarbonyldiimidazole.

The base may include organic bases such as triethylamine and pyridine. The solvent may include aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; aHphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; halogenated aromatic hydro- carbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or acid is poured into the reaction mixture and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Al-2]. The acid to be added may include hydrochloric acid, acetic acid, trifluoro- acetic acid, p-toluenesulfonic acid, and aqueous solutions thereof. The compound may be purified by a technique such as chromatography or recrystaUization.

Producing Process A4

[Al-2] IA4-1]

wherein R¹, R³⁰¹, X, Z, and Q are as defined above. The present compound [A4-1] can be produced by reacting compound

[Al-2] with a sulfurizing agent.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to 200°C. The reaction time is usuaUy in the range of a moment to 48 hours. The amount of sulfurizing agent to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [Al-1].

The sulfurizing agent may include diphosphorus pentasulfide and lawson reagent.

The solvent may include aromatic hydrocarbons such as toluene and xylene.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [A4-1]. The compound may be purified by a technique such as chromatography or recrystalHzation.

The foUowing wiU describe the producing processes for the present intermediates B as the intermediates useful for the production of the present compounds. The present intermediates B can be produced, for example, by the producing processes described in the foUowing Producing Processes Bl to B5.

Producing Process Bl

[Bl-3] [Bl-4] wherein R¹, R³², R²⁰¹, R³⁰¹, D, and X are as defined above; and R³³ is optionaUy substituted benzyl {e.g., benzyl). 1) Step of producing compound [Bl-2] from compound [Bl-1]

The compound [Bl-2] can be produced by reacting compound [Bl-1] and compound [Al-1] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The _/reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaHy in the range of a moment to 72 hours.

The amount of compound [Al-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [Bl-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [Bl-1].

The base may include inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride,

Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide; and metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniline, N,N-diethylaniHne, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or acid is poured into the reaction mixture and the deposited crystals are coUected by filtration; or acid is poured into the reaction mixture, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Bl-2]. The acid to be added may include hydrochloric acid, acetic acid, trifluoro- acetic acid, p-toluenesulfonic acid, and aqueous solutions thereof. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [Bl-3] from compound [Bl-2]

The compound [Bl-3] can be produced by reacting compound [Bl-2] and compound [1-2] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 48 hours. The amount of compound [1-2] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [Bl-2].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [Bl-2].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniHne, triethylamine, and dusopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide.

The solvent may include aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydro- carbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethyl- formamide and acetamide; tertiary amines such as pyridine, N,N-dimethyl- aniline, N,N-diethylanifine, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Bl-3]. The compound may be purified by a technique such as chromatography or recrystalHzation.

3) Step of producing compound [Bl-4] from compound [Bl-3] The reaction in this step can be carried out, for example, according to the process described in Synthesis, p. 846 (1994) or by the foUowing process.

The present intermediate B [Bl-4] can be produced by reacting compound [Bl-3] with hydrogen in the presence of a catalyst.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 150°C, preferably 0°C to 50°C. The reaction time is usuaUy in the range of a moment to 48 hours.

The reaction may also be carried out under increased pressure, preferably under a pressure of 1 to 5 atm.

The amount of catalyst to be used in the reaction is usuaUy in the range of 0.001% to 100% by weight based on the weight of compound [Bl-3].

The catalyst to be used in the reaction may include anhydrous paUadium/carbon and hydrated paUadium/carbons.

The solvent may include carboxyHc acids such as formic acid, acetic acid, and propionic acid; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitriles such as acetonitrile and isobutyro- nitrile; ethers such as 1,4-dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, t-butanol, amyl alcohol, isoamyl alcohol, and t-amyl alcohol; water; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Bl-4]. The compound may be purified by a technique such as chromatography or recrystaUization.

Producing Process B2

[Bl-2] [B2-1]

[B2-2] wherein R¹, R³⁰¹, R³³, X, and W are as defined above.

1) Step of producing compound [B2-1] from compound [Bl-2]

The compound [B2-1] can be produced by reacting compounds [Bl-2] and [2-1] in the presence of a base.

100°C. The reaction time is usuaUy in the range of a moment to 72 hours.

The amount of compound [2-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [Bl-2].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [Bl-2]. The base may include organic bases such as pyridine, 4-dimethyl- arninopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and dusopropylethylamine; metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium t-butoxide; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide.

The solvent may include aliphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; aHphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniline, N,N-diethylanihne, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsuHoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B2-1]. The compound may be purified by a technique such as chromatography or recrystaUization. 2) Step of producing compound [B2-2] from compound [B2-1]

The present intermediate B [B2-2] can be produced by reacting compound [B2-1] with hydrogen in the presence of a catalyst.

The amount of catalyst to be used in the reaction is usuaUy in the range of 0.001% to 100% by weight based on the weight of compound [B2-1].

The catalyst to be used in the reaction may include anhydrous paUadium/carbon and hydrated pafladium/carbons.

The solvent may include carboxyHc acids such as formic acid, acetic acid, and propionic acid; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitriles such as acetonitrile and isobutyro- nitrile; ethers such as 1,4-dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, t-butanol, amyl alcohol, isoamyl alcohol, and t-amyl alcohol; water; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B2-2].

The compound may be purified by a technique such as chromatography or recrystalHzation. Producing Process B3

[B3-3]

[B3-4] wherein R¹, R³³, R²⁰³, R³⁰³, V, and X are as defined above.

1) Step of producing compound [B3-3] from compound [B3-1] The compound [B3-3] can be produced by reacting compounds [B3-1] and [B3-2] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 48 hours. The amount of compound [B3-2] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [B3-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [B3-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-(Hethylaniline, triethylamine, and dusopropylethylamine; and inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide.

The solvent may include aHphatic hydrocarbons such as hexane, heptane, octane, and Hgroin; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; aHphatic halogenated hydro- carbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, and benzotrifluoride; ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitrobenzene; acid amides such as N,N-dimethylformamide; sulfur compounds such as dimethylsulfoxide and sulforane; water; and mixtures thereof.

The reaction may be carried out in a shortened reaction time by the addition of a phase transfer catalyst. The amount of phase transfer catalyst is usuaUy in the range of 0.001 mole to an excess for 1 mole of compound [B3-1]. The phase transfer catalyst may include tetrabutylammonium bromide and tetrabutylammonium chloride.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B3-3]. The compound may be purified by a technique such as chromatography or recrystaUization. 2) Step of producing compound [B3-4] from compound [B3-3]

The present intermediate B [B3-4] can be produced by reacting compound [B3-3] with hydrogen in the presence of a catalyst.

The reaction may also be carried out under increased pressure, preferably under a pressure of 1 to 5 atm. The amount of catalyst to be used in the reaction is usuaUy in the range of 0.001% to 100% by weight based on the weight of compound [B3-3].

The solvent may include carboxyHc acids such as formic acid, acetic acid, and propionic acid; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitriles such as acetonitrile and isobutyro- nitrile; ethers such as 1,4-dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, t-butanol, amyl alcohol, isoamyl alcohol, and t-amyl alcohol; water; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B3-4]. The compound may be purified by a technique such as chromatography or recrystalHzation.

Producing Process B4

[B4-1] [B4-2] [B4-3] wherein R¹, R²⁰³, R³⁰³, R³³, X, and Z are as defined above.

1) Step of producing compound [B4-2] from compound [B4-1]

The present compound [B4-2] can be produced by reacting compound [B4-1] with a sulfurizing agent. The reaction is usuaUy carried out in a solvent. The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usuaUy in the range of a moment to 48 hours.

The amount of sulfurizing agent to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [B4-1].

The sulfurizing agent may include diphosphorus pentasulfide and lawson reagent.

The solvent may include aromatic hydrocarbons such as toluene and xylene. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B4-2]. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [B4-3] from compound [B4-2]

The compound [B4-3] can be produced by reacting compound [B4-2] with hydrogen in the presence of a catalyst.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 150°C, preferably 0°C to 50°C. The reaction time is usuaUy in the range of a moment to 48 hours. The reaction may also be carried out under increased pressure, preferably under a pressure of 1 to 5 atm.

The amount of catalyst to be used in the reaction is usuaUy in the range of 0.001% to 100% by weight based on the weight of compound [B4-2]. The catalyst to be used in the reaction may include anhydrous paUadium/carbon and hydrated paUadium/carbons.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B4-3]. The compound may be purified by a technique such as chromatography or recrystaUization .

Producing Process B5

wherein R\ R³², R³³, R²⁰², R³⁰², and X are as defined above.

1) Step of producing compound [B5-1] from compound [Bl-1] The compound [B5-1] can be produced by reacting compounds [Bl-1] and [6-2] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 200°C, preferably 0°C to 100°C. The reaction time is usuaUy in the range of a moment to 72 hours. The amount of compound [6-2] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [Bl-1].

The base may include inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.

The solvent may include ketones such as acetone and methyl isobutyl ketone; aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide and acetamide; tertiary amines such as pyridine, N,N-dimethylani1ine, N,N-diethylaniHne, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, and t-butanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or acid is poured into the reaction mixture and the deposited crystals are coUected by filtration; or acid is poured into the reaction mixture, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B5-1]. The acid to be added may include hydrochloric acid, acetic acid, trifluoro- acetic acid, p-toluenesulfonic acid, and aqueous solutions thereof. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [B5-2] from compound [B5-1] The present intermediate B [B5-2] can be produced by reacting compound [B5-1] with hydrogen in the presence of a catalyst.

The amount of catalyst to be used in the reaction is usuaUy in the range of 0.001% to 100% by weight based on the weight of compound [B5-1]. The catalyst to be used in the reaction may include anhydrous paUadium/carbon and hydrated paUadium/carbons.

The solvent may include carboxyHc acids such as formic acid, acetic acid, and propionic acid; esters such as ethyf formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitriles such as acetonitrile and isobutyro- nitrile; ethers such as 1,4-dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, t-butanol, amyl alcohol, isoamyl alcohol, and t-amyl alcohol; water; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [B5-2].

The compound may be purified by a technique such as chromatography or recrystaUization.

The foUowing will describe the producing processes for various intermediates in the production of the present compounds and intermediates A and B.

The compound [5-2] is commerciaUy avadable or can be produced, for example, according to the process described in "Jikken Kagaku Koza" (Maruzen Co., Ltd.), 4th ed., vol. 19, pp. 363-482. The compound [8-2] is commerciaUy available or can be produced, for example, according to the processes described in Journal of Organic

Chemistry, vol. 28, pp. 1903-1905 (1963); Journal of the American Chemical

Society, vol. 73, pp. 2379-2380 (1951); Organic Synthesis, vol. 68, pp. 8-12; and Journal of Fluorine Chemistry, vol. 12, pp. 437-438 (1978).

The compounds [9-2] and [11-1] are commerciaUy avaflable or can be produced, for example, according to the process described in Bioorganic and Medicinal Chemistry Letters, vol. 5, p. 1035 (1995).

The compounds [6-1] and [A2-1] wherein Z is oxygen can be produced, for example, according to the process described in the foUowing Reference Producing Process 1.

Reference Producing Process 1

[Cl-5]

wherein R³², V, W, Q, and X are as defined above. 1) Step of producing compound [Cl-2] from compound [Cl-1]

The compound [Cl-2] can be produced by reacting compounds [Cl-1] and [2-1] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of -20°C to 150°C. The reaction time is usuaUy in the range of a moment to 72 hours. The amount of compound [2-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [Cl-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [Cl-1].

The base may include organic bases such as pyridine, 4-dimethyl- aminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, and l,4-diazabicyclo[2.2.2]octane; inorganic bases such as sodium carbonate, potassium carbonate, Hthium carbonate, sodium hydride, potassium hydride, Hthium hydride, sodium hydroxide, potassium hydroxide, and Hthium hydroxide; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.

The solvent may include aHphatic hydrocarbons such as hexane, heptane, octane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; aHphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, and 1,2,3-trichloropropane; ethers such as diethyl ether, dusopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitriles such as acetonitrile and isobutyronitrile; acid amides such as N,N-dimethylform- amide and acetamide; tertiary amines such as pyridine, N,N-dimethylaniline, N,N-(HethylaniHne, triethylamine, and dusopropylethylamine; sulfur compounds such as dimethylsulfoxide and sulforane; water; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Cl-2]. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [Cl-4] from compound [Cl-2]

The compound [Cl-4] can be produced, for example, according to the processes described in Journal of Organic Chemistry, vol. 60, pp. 7010-7012

(1995); Synthetic Communications, vol. 15, pp. 697-706 (1985); and the patent specification of U.S. Patent 4,358,611, or can be produced by the foUowing process.

Producing process by reacting compounds [Cl-2] and [Cl-3] in the presence of a base.

The reaction is usuaUy carried out in a solvent; however, it may also be carried out without any solvent The reaction temperature is usuaUy in the range of -20°C to 200°C. The reaction time is usually in the range of a moment to 48 hours.

The amount of compound [Cl-3] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [Cl-2].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [Cl-2].

The base may include pyridine, triethylamine, and dusopropylethyl- amine.

The solvent may include chloroform, tetrahydrofuran, water, and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post- treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [Cl-4]. The compound may be purified by a technique such as chromatography or recrystaUization.

3) Step of producing compound [Cl-5] from compound [Cl-2] The compound [Cl-5] can be produced from compound [Cl-2], for example, according to the process described in "Jikken Kagaku Koza" (Maruzen Co., Ltd.), 4th ed., vol. 20, pp. 360-365.

4) Step of producing compound [Cl-5] from compound [Cl-4] The compound [Cl-5] can be produced from compound [Cl-4], for example, according to the process described in Journal of the American Chemical Society, vol. 80, pp. 3932-3937 (1958).

The compound [6-1] wherein Z is sulfur can be produced, for example, according to the process described in Chemistry Letters, pp. 1385-1386 (1988).

The compound [A2-1] wherein Z is sulfur can be produced, for example, by the process described in the foUowing Reference Producing Process 2.

Reference Producing Process 2

X X

^-OR³² ► ^-NH₂

Q-S-NH Q-S-NH

[C2-1] [C2-2] wherein R³², Q, and X are as defined above. The compound [C2-2] can be produced from compound [C2-1], for example, according to the process described in Journal of the American Chemical Society, vol. 80, pp. 3932-3937 (1958),

The compound [A3-1] can be produced, for example, according to the process described in "Jikken Kagaku Koza" (Maruzen Co., Ltd.), 4th ed., vol. 22, pp. 137-151. The compound [Bl-1] is commerciaUy available or can be produced, for example, according to the process described in Journal of Medicinal Chemistry, vol. 10, pp. 556-564 (1967).

The compounds [8-1] and [B3-1] can be produced according to the process described in the pubHshed specification of WO98/08824, or can also be produced, for example, by the process described in the foUowing Reference

Producing Process 3.

Reference Producing Process 3

[C3-5] [C3-6] wherein R¹, R³², R²⁰¹, R³⁰¹, D, and V are as defined above; and R²⁰⁶ and R²⁰⁷ are the same or different and independently hydrogen, d-C₅ alkyl or optionaUy substituted phenyl {e.g., phenyl, 2-nitrophenyl), with the proviso that R²⁰⁶ and R²⁰⁷ are not hydrogen at the same time.

1) Step of producing compound [C3-3] from compound [C3-1]

The compound [C3-3] can be produced by reacting compounds [C3-1] and [C3-2] in the presence of a base. The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to the reflux temperature of the solvent. The reaction time is usuaUy in the range of a moment to 24 hours.

The amount of compound [C3-2] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [C3-1].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [C3-1].

The base may include N,N-dimethylani1in e and pyridine. The solvent may include ethers such as tetrahydrofuran; acid amides such as N,N-dimethylformamide; and aromatic hydrocarbons such as benzene and toluene.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [C3-3]. The compound may be purified by a technique such as chromatography or recrystaUization.

2) Step of producing compound [C3-4] from compound [C3-3]

The compound [C3-4] can be produced by reacting compounds [C3-3] and [Al-1] in the presence of a base. The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to the reflux temperature of the solvent. The reaction time is usuaUy in the range of a moment to 96 hours.

The amount of compound [Al-1] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [C3-3].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [C3-3]. The base may include inorganic bases such as sodium hydride; and metal alcoholates such as sodium methylate and sodium ethylate.

The solvent may include ethers such as tetrahydrofuran; acid amides such as N,N-dimethylformamide; and aromatic hydrocarbons such as benzene and toluene. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [C3-4]. The compound may be purified by a technique such as chromatography or recrystaUization.

3) Step of producing compound [C3-5] from compound [C3-4]

The compound [C3-5] can be produced by reacting compounds [C3-4] and [1-2] in the presence of a base.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to the reflux temperature of the solvent. The reaction time is usuaUy in the range of a moment to 96 hours. The amount of compound [1-2] to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, for 1 mole of compound [C3-4].

The amount of base to be used in the reaction is usuaUy in the range of 0.5 equivalent to an excess, preferably 0.8 to 1.2 equivalents, relative to compound [C3-4].

The base may include inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; and metal alcoholates such as sodium methylate and sodium ethylate. The solvent may include ethers such as tetrahydrofuran; acid amides such as N,N-dimethylformamide; and aromatic hydrocarbons such as benzene and toluene.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [C3-5]. The compound may be purified by a technique such as chromatography or recrystaUization.

4) Step of producing compound [C3-6] from compound [C3-5]

The compound [C3-6] can be produced by reacting compound [C3-5] under the reduction conditions. The reduction conditions for producing compound [C3-6] may include, for example, the foUowing conditions: Reaction Conditions 1

The compound [C3-6] is produced by reacting compound [C3-5] with iron powder in the presence of an acid.

The reaction is usuaUy carried out in a solvent. The reaction temperature is usuaUy in the range of room temperature to the reflux temperature of the solvent. The reaction time is usuaUy in the range of a moment to 96 hours.

The amount of iron powder to be used in the reaction is usuaUy in the range of 0.5 mole to an excess, preferably 0.8 to 1.2 moles, relative to compound [C3-5].

The amount of acid to be used in the reaction is usuaUy in the range of 1 equivalent to an excess, preferably 1 to 10 equivalents, relative to compound [C3-5]. The acid may include organic acids such as p-toluenesulfόnic acid, acetic acid, and propionic acid; and inorganic acids such as hydrochloric acid and sulfuric acid.

The solvent may include aliphatic hydrocarbons such as hexane, heptane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chloro- benzene, and dichlorobenzene; ethers such as diethyl ether, dusopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides formamide, N,N-dimethylform- amide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-diethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, isopropanol, and ethylene glycol; water; and mixtures thereof.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [C3-6]. The compound may be purified by a technique such as chromatography or recrystaUization.

Reaction Conditions 2

The compound [C3-6] is produced by reacting compound [C3-5] with hydrogen in the presence of a catalyst.

The reaction is usuaHy carried out in a solvent. The reaction temperature is usuaUy in the range of 0°C to 150°C, preferably 0°C to 50°C. The reaction time is usuaUy in the range of a moment to 96 hours.

The amount of catalyst to be used in the reaction is usuaUy in the range of 0.001% to 100% by weight based on the weight of compound [C3-5].

The catalyst to be used in the reaction may include anhydrous paUadium/carbon and hydrated paUadium/carbons. The solvent may include aHphatic hydrocarbons such as hexane, heptane, Hgroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chloro- benzene, and dichlorobenzene; ethers such as diethyl ether, dusopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, dusopropylethylamine, N,N-dimethylaniline, N,N-diethylaniHne, and N-methylmorphoHne; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, isopropanol, and ethylene glycol; water; and mixtures thereof. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments, for example, the reaction mixture is filtered and the filtrate is then concentrated without further treatment; or the reaction mixture is poured into water and the deposited crystals are coUected by filtration; or the reaction mixture is poured into water, foUowed by extraction with an organic solvent and concentration, thus obtaining compound [C3-6]. The compound may be purified by a technique such as chromatography or recrystaUization.

The present compounds have exceUent herbicidal activity and some of them can exhibit exceUent selectivity between crops and weeds. In other words, the present compounds have herbicidal activity against various weeds which may cause some trouble in the foHar treatment and sofl treatment on upland fields, such as Hsted below.

Polygonaceous weeds: wfld buckwheat {Polygonum convolvulus), pale smartweed {Poly- gonum lapathioliuni), Pennsylvania smartweed {Polygonum pensylvanicum), ladysthumb {Polygonum persicaria), curly dock {Rumex crispus), broadleaf dock {Rumex obtusifolius), Japanese knotweed {Polygonum cuspidatum)

Portulacaceous weeds: common purslane {Portulaca oleracea) CaryophyUaceous weeds: common duckweed {Stellaria media)

Chenopodiaceous weeds: common lambsquarters {Chenopodium album), kochia {Kochia scoparia)

Amaranthaceous weeds: redroot pigweed {Amaranthus retroflexus), smooth pigweed {Amaranth us hybridus) Cruciferous (brassicaceous) weeds: wild radish {Raphanus raphanistrum) , wfld mustard {Sinapis arvensis), shepherdpurse {Capsella bursa-pastoris)

Leguminous (fabaceous) weeds: hemp sesbania {Sesbania exaltata), sicklepod {Cassia obtusifolia), Florida beggarweed {Desmodium tortuosum), white clover {Trifolium repens)

Malvaceous weeds: velvetleaf {Abutilon theophrasti), prickly sida {Sida spinosa)

"Violaceous weeds: field pansy ( viola arvensis), wfld pansy ( Viola tricolor) Rubiaceous weeds: catch weed bedstraw (cleavers) {Galium aparine)

Convolvulaceous weeds: ivyleaf morningglory {Ipomoea hederacea), taU morningglory {Ipomoea purpurea), entireleaf morningglory {Ipomoea hederacea var. integriuscula), pitted morningglory {Ipomoea lacunosa), field bindweed {Convolvulus arvensis)

Labiate weeds: red deadnettle {Lamium purpureum), henbit {Lamium amplexicaule)

Solanaceous weeds: jimsonweed {Datura stramonium), black nightshade {Solanum nigrum)

Scrophulariaceous weeds: birdseye speedweU { Veronica persica), ivyleaf speedweU {Veronica hederaefolia)

Composite weeds: common cocklebur (Xanthium pensylvanicum), common sunflower {Helianthus annuus), scentless chamoπύle {Matricaria perforata or inodora), corn marigold {Chrysanthemum segetum), pineappleweed {Matricaria matricarioides), common ragweed {Ambrosia artemisii folia), giant ragweed {Ambrosia trifida), horseweed {Erigeron canadensis), Japanese mugwort {Artemisia princeps), taU goldenrod {Solidago altissima)

Boraginaceous weeds: forget-me-not {Myosotis arvensis)

Asclepiadaceous weeds: common milkweed {Asclepias syriaca)

Euphorbiaceous weeds: sun spurge {Euphorbia hehoscopia), spotted spurge {Euphorbia macula ta)

Graminaceous weeds: barnyardgrass {Echinochloa crus-galh), green foxtaU {Setaria viridis), giant foxtail {Setaria faberi), large crabgrass {Digitaria sanguinalis), goosegrass {Eleusine indica), annual bluegrass {Poa annua), blackgrass {Alopecurus myosuroides), wfld oats {Avena fatua), johnsongrass {Sorghum halepense), quackgrass {Agropyron repens), downy brome {Bro us tecto- ru ), bermudagrass {Cynodon dactyloή), faU panicum {Panicum dichoto- miflorum), Texas panicum {Panicum texanum), shattercane {Sorghum vulgare) Commelinaceous weeds: common dayflower {Commelina communis)

Equisetaceous weeds: field horsetail {Equisetum arvense) Cyperaceous weeds: rice flatsedge {Cyperus iria), purple nutsedge {Cyperus rotundus), yeUow nutsedge {Cyperus esculentus)

Furthermore, some of the present compounds exhibit no significant phytotoxicity on the main crops such as corn {Zea mays), wheat {Triticum aestivum), barley {Hordeum vulgare), rice {Oryza sativa), sorghum {Sorghum bicolor), soybean {Glycine max), cotton {Gossypium spp.), sugar beet (β vulgaris), peanut {Arachis hypogaea), sunflower {Helianthus annuus), and canola {Brassica napus); horticultural crops such as flowers and ornamental plants; and vegetable crops.

The present compounds can also attain the effective control of various weeds which may cause some trouble in the no-tiHage cultivation of soybean {Glycine max), corn {Zea mays), wheat {Triticum aestivum), and other crops. Furthermore, some of the present compounds exhibit no significant phytotoxicity on the crops.

The present compounds also have herbicidal activity against various weeds which may cause some trouble in the flooding treatment on paddy fields, such as listed below.

Graminaceous weeds: barnyardgrass {Echinochloa oryzicola)

Scrophulariaceous weeds: common falsepimpemel {Lindernia procumbens)

Lythraceous weeds:

Indian toothcup {Rotala indica), red stem {Ammannia multiflora) Elatinaceous weeds: waterwort {Elatine triandra)

Cyperaceous weeds: smaUflower umbreUa sedge {Cyperus difformis), hardstem bulrush {Scirpus juncoides), needle spikerush {Eleocharis acicularis), water nutgrass {Cyperus serotinus), water chestnut {Eleocharis kuroguwai)

Pontederiaceous weeds: monochoria {Monochoria vaginalis) AHsmataceous weeds: arrowhead {Sagittaria pygmaea), arrowhead {Sagittaria trifolia), waterplantain {Alisma canaliculatum)

Potamogetonaceous weeds: roundleaf pondweed {Potamogeton distinctus) UmbeUoferous weeds: watercelery sp. {Oenanthe javanica)

Furthermore, some of the present compounds exhibit no significant phytotoxicity on transplanted paddy rice.

The present compounds can also attain the control of a wide variety of weeds which are growing or wiH grow in the orchards, grasslands, lawns, forests, waterways, canals, or other non-cultivated lands.

The present compounds also have herbicidal activity against various aquatic weeds, such as water hyacinth {Eichhornia crassipes), which are growing or wiU grow at the waterside such as waterways or canals. The present compounds have substantiaUy the same characteristics as those of the herbicidal compounds disclosed in the pubHshed specification of International Patent Apphcation, WO95/34659. In the case where crops with tolerance imparted by introducing a herbicide tolerance gene described in the pubHshed specification are cultivated, the present compounds can be used at larger rates than those used when ordinary crops without tolerance are cultivated, which makes it possible to control other unfavorable weeds more effectively.

When the present compounds are used as the active ingredients of herbicides, they are usuaUy mixed with sohd or Hquid carriers or diluents, surfactants, and other auxLHary agents to give emulsifiable concentrates, wettable powders, flowables, granules, concentrated emulsions, water- dispersible granules, or other formulations. These formulations may contain any of the present compounds as an active ingredient at an amount of 0.001 to 80% by weight, preferably 0.005 to 70% by weight, based on the total weight of the formulation.

The solid carrier or diluent which can be used may include, for example, fine powders or granules of the foUowing materials : mineral mat- ters such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyUite, talc, diatomaceous earth, and calcite; organic substances such as walnut sheU powder; water-soluble organic substances such as urea; inorganic salts such as ammonium sulfate; and synthetic hydrated siHcon oxide. The Hquid carrier or diluent which can be used may include, for example, aromatic hydrocarbons such as methylnaphthalene, phenylxylylethane, and alkyl- benzene {e.g., xylene); alcohols such as isopropanol, ethylene glycol, and 2-ethoxyethanol; esters such as phthahc acid dialkyl esters; ketones such as acetone, cyclohexanone, and isophorone; mineral oils such as machine oU; vegetable ofls such as soybean oil and cottonseed oil; dimethylsulfoxide, N,N-dimethylformamide, acetonitrile, N-methylpyrroHdone, and water.

The surfactant used for emulsification, dispersing, or spreading may include surfactants of the anionic type, such as alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl aryl ethers; and surfactants of the nonionic type, such as polyoxy- ethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.

The auxiliary agent may include Hgnin sulfonates, alginates, poly- vinyl alcohol, gum arabic, CMC (carboxymethylceUulose), and PAP (isopropyl acid phosphate).

The present compounds are usuaUy formulated as described above and then used for pre- or post-emergence sofl, fohar, or flooding treatment of weeds. The sofl treatment may include sofl surface treatment and soil incorporation. The fohar treatment may include appHcation over the plants and directed appHcation in which a chemical is appHed only to weeds so as to keep off the crop plants.

The present compounds may often exhibit the enhancement of herbi- cidal activity when used in aώnixture with other herbicides. They can also be used in admixture with insecticides, acaricides, nematocides, fungicides, bactericides, plant growth regulators, fertilizers, and soil conditioners.

Examples of the herbicide which can be used in admixture with the present compounds are atrazine, cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn, chlorotoluron, diuron, daimuron, fluo- meturon, isoproturon, linuron, methabenzthiazuron, bromoxynil, ioxynil, ethalfluralin, pendimethalin, trifluralin, acifluorfen, acifluorfen-sodium, bifenox, chlomethoxynil, fomesafen, lactofen, oxadiazon, oxadiargyl, oxy- fluorfen, carfentrazone-ethyl, flumiclorac-pentyl, flumioxazine, fluthiacet- methyl, sulfentrazone, thidiazimin, azafenidin, pyraflufen-ethyl, cinidon- ethyl, fluazolate, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, DCPA, MCPA, MCPB, clomeprop, clopyralid, dicamba, dithiopyr, fluroxypyr, mecoprop, naploaniHde, phenothiol, quinclorac, triclopyr, thiazopyr, acetochlor, alachlor, butachlor, diethatyl-ethyl, metolachlor, pretilachlor, propachlor, bensulfuron-methyl, chlorsuHuron, chlorimuron-ethyl, halosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron-methyl, pyrazosulfuron- ethyl, sulfometuron-ethyl, thifensulfuron-methyl, triasulfuron, tribenuron- methyl, oxasulfuron, azimsulfuron, cloransulam-methyl, cyclosulfamuron, flumetsulam, flupyrsulfuron, flazasulfuron, imazosulfuron, metosulam, diclosulam, prosulfuron, rimsulfuron, triflusulfuron-methyl, ethoxysulfuron, sulfosulfuron, flucarbazone, indosulfuron, imazamethabenz-methyl, imaza- pyr, imazaquin, imazethapyr, imazameth, imazamox, imazapic, bispyribac- sodium, pyriminobac-methyl, pyrithiobac-sodium, aUoxydim-sodium, cletho- di , sethoxydim, tralkoxydim, tepraloxydim, dichlofop -methyl, fenoxaprop- ethyl, fenoxaprop-p-ethyl, fluazifop-buthyl, fluazifop-p -butyl, haloxyfop- methyl, quizalofop-p-ethyl, cyhalofop-butyl, clodinafop-propargyl, benzo- fenap, clomazone, diflufenican, norflurazone, pyrazolate, pyrazoxyfen, flurtamone, isoxaflutole, isoxachlortole, sulcotrione, mesotrione, glufosinate- ammonium, glyphosate, bentazone, benthiocarb, bromobutide, butamifos, butylate, dimepiperate, dimethenamid, DSMA, EPTC, esprocarb, isoxaben, mefenacet, moHnate, MSMA, piperophos, pyributicarb, propanil, pyridate, triaUate, cafenstrol, flupoxam, fluthiamide, diflufenzopyr, triaziflam, pent- oxazone, epoprodan, metobenzuron, oxaziclomefone, and pyribenzoxim.

The above comp ounds are described in the catalog of Farm Chemicals Handbook, 1995 (Meister PubHshing Company); AG CHEM NEW COMPOUND REVIEW, VOL. 13, 1995 or VOL. 15, 1997 (AG CHEM INFORMATION SERVICES); AGROW, Nos. 287, 296, and 297, 1998 (PJB PubHcations Ltd.); or "Josouzai Kenkyu Souran" (Hakuyu-sha).

When the present compounds are used as the active ingredients of herbicides, the appHcation amount, although it may vary with the weather conditions, formulation types, appHcation times, appHcation methods, soil conditions, crops to be protected, weeds to be controUed, and other factors, is usuaUy in the range of 0.1 to 50,000 g, preferably 1 to 10,000 g, per hectare. In the case of emulsifiable concentrates, wettable powders, flowables, concentrated emulsions, water- dispersible granules, or other similar formulations, they are usuaUy apphed after diluted in their prescribed amounts with water (if necessary, containing an adjuvant such as a spreading agent) at a ratio of 10 to 1000 Hters per hectare. In the case of granules or some types of flowables, they are usuaUy apphed as such without any dilution.

The adjuvant which can be used, if necessary, may include, in addition to the surfactants as described above, polyoxyethylene resin acids

(esters), Hgnin sulfonates, abietates, diuaphthylmethanecHsulfonates, crop ofl concentrates, and vegetable oils such as soybean oil, corn oil, cottonseed oil, and sunflower oil.

The present compounds can also be used as the active ingredients of harvesting aids such as defoHants and desiccants for cotton {Gossipyum spp.), and desiccants for potato {Solanum tuberosum). In these cases, the present compounds are usuaUy formulated in the same manner as the case where they are used as the active ingredients of herbicides, and used alone or in admixture with other harvesting aids for foHar treatment before the harvesting of crops.

Examples

The present invention wiU be further fllustrated by the foUowing production examples, formulation examples, and test examples; however, the present invention is not limited to these examples. The foUowing wiU describe the production examples for the present compounds. The present compounds are designated by their compound numbers which are defined as a combination of the structural formula numbers I to XVT and the sub-group numbers shown in Tables 1 to 30; or as a combination of the structural formula number XVII and the sub-group numbers shown in Tables 31 and 32. Production Example 1

A mixture of 315 mg of compound [1-a], 212 mg of 4-fluoronitro- benzene, 249 mg of potassium carbonate, and 6 ml of dimethyl sulfoxide was stirred at 70°C for 2 hours. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 3 : 1) to give 82 mg of compound [1-b] (the present compound no. 1-89).

Η-NMR (CDC1₃, 250 MHz) δ (ppm): 3.60 (q, 3H, J = 1.3 Hz), 6.40 (s, IH), 7.1-7.2 (m, 2H), 8.2-8.3 (m, 2H)

Production Example 2

A mixture of 50 mg of compound [1-a], 38 mg of 3,4-difluoronitro- benzene, 39 mg of potassium carbonate, and 1.5 ml of dimethyl sulfoxide was stirred at 70°C for 1 hours. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 3 : 1) to give 39 mg of compound [1-c] (the present compound no. 1-587).

Η-NMR (CDC1₃, 250 MHz) δ (ppm): 3.60 (q, 3H, J = 1.3 Hz), 6.38 (s, IH), 7.10 (dd, IH, J = 9.1, 7.9 Hz), 8.0-8.1 (m, IH), 8.10 (dd, IH, J = 9.1, 2.6 Hz)

Production Example 3

A mixture of 53 mg of compound [1-a], 47 mg of 5-chloro-2-nitro- anisole, 41 mg of potassium carbonate, and 2 ml of dimethyl sulfoxide was stirred at 70°C for 1 hours. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane : ethyl acetate = 2 : 1) to give 7 mg of compound [1-d] (the present compound no. 1-115).

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 3.60 (q, 3H, J = 1.1 Hz), 3.98 (s, 3H), 6.38 (s, IH), 6.51 (dd, IH, J = 9.3, 2.8 Hz), 6.89 (d, IH, J = 2.8 Hz), 7.94 (d, IH, J = 9.3 Hz) For some compounds produced by the same producing process as described in Production Examples 1 to 3, their present compound numbers and physical properties are shown below. The present compound no. 1-91 m.p.: 130.0°C The present compound no. 1-106 m.p.: 122.9°C

The present compound no. 1-108 m.p.: 193.2°C

The present compound no. 1-109 m.p.: 187.4°C

The present compound no. 1-116 m.p.: 166.6°C

The present compound no. 1-118 m.p.: 121.8°C The present compound no. 1-123 m.p.: 117.2°C

The present compound no. 1-126 m.p.: 113.7°C

The present compound no. 1-127 m.p.: 54.4°C

The present compound no. 1-134 m.p.: 134.6°C

Production Example 4

To a mixture of 2.59 g of compound [4-a], 20 ml of dichloromethane, and 7 ml of tetrahydrofuran was added dropwise 1.23 ml of 32% peracetic acid at room temperature. Then, 0.86 g of copper (II) acetate and 1.0 g of compound [1-a] were added thereto, foUowed by stirring overnight. The reaction mixture was heated under reflux for 2 hours and then cooled to room temperature. Saturated aqueous sodium hydrogensulfite solution and

IN hydrochloric acid were added thereto, followed by filtration through CeHte. The filtrate was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) to give 190 mg of compound [1-e] (the present compound no. 1-3). m.p.: 128.6°C

For some compounds produced by the same producing process as described in Production Example 4, their present compound numbers and physical properties are shown below. The present compound no. 1-4 m.p.: 154.2°C

The present compound no. 1-5 m.p.: 105.4°C

The present compound no. 1-7 m.p.: 106.3°C

The present compound no. 1-8 m.p.: 154.0°C

The present compound no. 1-85 m.p.: 94.7°C The present compound no. 1-87 m.p.: 141.2°C

The present compound no. 1-88 m.p.: 170.9°C

The present compound no. 1-351 m.p.: 127.2°C

The present compound no. 1-585 m.p.: 105.7°C

The present compound no. 1-694 m.p.: 95.5°C Production Example 5

A mixture of 106 mg of compound [2-a], 71 mg of 4-fluoronitro- benzene, 69 mg of potassium carbonate, and 3 ml of dimethyl sulfoxide was stirred at 60°C for 1 hour. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was washed with isopropanol and then with hexane to give 29 mg of compound [2-b] (the present compound no. 11-89).

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 4.67 (bs, 2H), 6.31 (s, IH), 7.1- 7.2 (m, 2H), 8.2-8.3 (m, 2H)

Production Example 6

To a mixture of 1.0 g of compound [3-a], 0.2 g of tetrabutylammonium chloride, 4.8 g of sodium carbonate, 60 ml of chloroform, and 120 ml of water was added 1.3 g of 2-nitrophenylsulfenyl chloride at room temperature. The reaction mixture was stirred at room temperature for 1 hour and then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : chloroform = 1 : 1) to give 50 mg of compound [3-b] (the present compound no. IX-79).

Η-NMR (CDC1₃, 300MHz) δ (ppm): 3.60 (q, 3H, J = 1.1 Hz), 6.41 (s, IH), 6.91 (dd, IH, J = 8.2, 1.0 Hz), 7.3-7.4 (m, IH), 7.5-7.7 (m, IH), 8.36 (dd, IH, J = 8.4, 1.3 Hz) Production Example 7

A mixture of 1.0 g of compound [1-a], 1.03 g of methyl 3-chloro-6- nitrobenzoate, 0.72 g of potassium carbonate, and 30 ml of dimethyl sulfoxide was stirred at 70°C for 1 hour. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The soHd obtained was washed with hexane to give 0.89 g of compound [1-f] (the present compound no. 1-301). Η-NMR (CDCI₃, 250 MHz) δ (ppm): 3.60 (q, 3H, J = 1.2 Hz), 3.92 (s,

3H), 6.38 (s, IH), 7.25-7.30 (m, 2H), 8.00-8.06 (m, IH) Production Example 8

Step 1

A mixture of 1.59 g of compound [1-a], 2.10 g of 2,4-difluoronitro- benzene, 0.41 g of Hthium carbonate, and 50 ml of dimethyl sulfoxide was stirred at 80°C for 3 hours. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) to give 1.82 g of compound [1-g] (the present compound no. 1-105). m.p.: 151.2°C

Step 2

To 175 mg of compound [1-g] were added 1 ml of N,N-dimethylform- amide and 60 mg of propylamine. The reaction mixture was stirred at room temperature for 16 hours and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 1 : 1) to give 100 mg of compound [1-h] (the present compound no. 1-202).

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 1.05 (t, 3H, J = 7.3 Hz), 1.76 (tq, 2H, J = 7.3, 7.0 Hz), 3.23 (dt, 2H, J = 7.0, 7.0 Hz), 3.59 (q, 3H, J = 1.0 Hz), 6.16 (dd, IH, J = 9.5, 2.6 Hz), 6.38 (s, IH), 6.50 (d, IH, J = 2.6 Hz), 8.18 (d, IH, J = 9.5Hz), 8.1-8.3 (m,lH)

For some compounds produced by the same producing process as described in Production Example 8, their present compound numbers and physical properties are shown below.

The present compound no. 1-201

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.37 (t, 3H, J = 7.1 Hz), 3.2-3.4 (m, 2H), 3.59 (q, 3H, J = 1.1 Hz), 6.17 (dd, IH, J = 9.5, 2.8 Hz), 6.38 (s, IH), 6.50 (d, IH, J = 2.8 Hz), 8.0-8.2 (m, IH), 8.18 (d, IH, J = 9.5Hz)

The present compound no. 1-203 m.p.: 113.0°C

The present compound no. 1-204 Η-NMR (CDC1₃, 300 MHz) δ (ppm): 0.6-0.7 (m, 2H), 0.8-1.0 (m, 2H),

2.5-2.6 (m, IH), 3.60 (s, 3H), 6.22 (dd, IH, J = 9.5, 2.8 Hz), 6.39 (s, IH), 6.98 (d, IH, J = 2.8 Hz), 8.17 (d, IH, J = 9.5 Hz), 8.1-8.3 (m,lH)

The present compound no. 1-205

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 0.98 (t, 3H, J = 7.3 Hz), 1.4-1.6 (m, 2H), 1.6-1.8 (m, 2H), 3.2-3.3 (m, 2H), 3.60 (q, 3H, J = 1.3 Hz), 6.16 (dd, IH, J = 9.5, 2.7 Hz), 6.38 (s, IH), 6.51 (d, IH, J = 2.7 Hz), 8.19 (d, IH, J = 9.5 Hz), 8.1-8.3 (m, IH)

The present compound no. 1-206

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.49 (s, 9H), 3.60 (m, 3H), 6.16 (dd, IH, J = 9.5, 2.6 Hz), 6.38 (s, IH), 6.75 (d, IH, J = 2.6 Hz), 8.20 (d, IH, J = 9.5 Hz), 8.4-8.6 (b, IH)

The present compound no. 1-208

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 1.3-1.5 (m, 6H), 1.6-1.7 (m, IH), 1.7-1.9 (m, 2H), 2.0-2.1 (m, IH), 3.3-3.5 (m, IH), 3.60 (q, 3H, J = 1.2 Hz), 6.10 (dd, IH, J = 9.5, 2.7 Hz), 6.38 (s, IH), 6.55 (d, IH, J = 2.7 Hz), 8.18 (d, IH, J = 9.5 Hz), 8.24 (d, IH, J = 7.6 Hz)

The present compound no. 1-214 m.p.: 165.8°C

The present compound no. 1-220 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 3.60 (q, 3H, J = 1.0 Hz), 3.83 (s,

IH), 4.06 (d, 2H, J = 5.1 Hz), 6.28 (dd, IH, J = 9.3, 2.4 Hz), 6.36 (d, IH, J = 2.4 Hz), 6.38 (s, IH), 8.23 (d, IH, J = 9.3 Hz), 8.5-8.6 (m, IH)

The present compound no. 1-221 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.32 (t, 3H, J = 7.2 Hz), 3.60 (q, 3H, J = 1.0 Hz), 4.04 (d, IH, J = 5.1 Hz), 4.29 (q, 3H, J = 7.2 Hz), 6.28 (dd, IH, J = 9.5, 2.6 Hz), 6.37 (d, IH, J = 2.6 Hz), 6.37 (s, IH), 8.23 (d, IH, J = 9.5 Hz), 8.5-8.6 (m, IH) The present compound no. 1-246

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 2.69 (t, 2H, J = 6.6 Hz), 3.5-3.7 (m, 5H), 3.71 (s, 3H), 6.27 (dd, IH, J = 9.5, 2.7 Hz), 6.38 (s, IH), 6.56 (d, IH, J = 2.7 Hz), 8.21 (d, IH, J = 9.5 Hz), 8.3-8.4 (m, IH)

The present compound no. 1-249 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.97 (tt, 2H, J = 6.3, 5.4 Hz),

3.37 (s, 3H), 3.3-3.5 (m, 2H), 3.52 (t, 2H, J = 5.4 Hz), 3.59 (q, 3H, J = 1.0 Hz), 6.18 (dd, IH, J = 9.3, 2.8 Hz), 6.37 (s, IH), 6.52 (d, IH, J = 2.8 Hz), 8.19 (d, IH, J = 9.3 Hz), 8.4-8.5 (m, IH)

The present compound no. 1-251 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.9-2.1 (m, 2H), 2.50 (t, 3H, J =

6.8 Hz), 3.36 (dt, 2H, J = 6.3, 5.4 Hz), 3.58 (q, 3H, J = 1.0 Hz), 6.26 (dd, IH, J = 9.7, 2.6 Hz), 6.38 (s, IH), 6.54 (d, IH, J = 2.6 Hz), 8.20 (d, IH, J = 9.7 Hz), 8.28 (d, IH, J = 5.4 Hz)

The present compound no. 1-253 Η-NMR (CDCI₃, 250 MHz) δ (ppm): 1.27 (t, 3H, J = 7.1 Hz), 1.97 (tt,

2H, J = 6.7, 6.1 Hz), 2.42 (t, 3H, J = 6.7 Hz), 3.2-3.4 (m, 2H), 3.59 (q, 3H, J = 1.1 Hz), 4.11 (q, 2H, J = 7.1 Hz), 6.29 (dd, IH, J = 9.5, 2.7 Hz), 6.37 (s, IH), 6.56 (d, IH, J = 2.7 Hz), 8.20 (d, IH, J = 9.5 Hz), 8.3-8.4 (m, IH)

The present compound no. 1-258 Η-NMR (CDCI₃, 250 MHz) δ (ppm): 1.05 (d, 3H, J = 6.8 Hz), 1.10 (d,

3H, J = 6.9 Hz), 2.2-2.3 (m, IH), 3.60 (q, 3H, J = 1.3 Hz), 3.73 (s, 3H), 3.8-3.9 (m, IH), 6.3-6.4 (m, IH), 6.38 (d, IH, J = 2.6 Hz), 6.37 (s, IH), 8.2-8.3 (m, IH), 8.5-8.6 (m, IH) The present compound no. 1-259

Η-NMR (CDC1₃, 250 MHz) δ (ppm): 0.9-1.0 (m, 3H), 1.0-1.1 (m, 3H), 1.7-1.9 (m, 3H), 3.60 (q, 3H, J = 1.3 Hz), 3.72 (s, 3H), 4.0-4.2 (m, IH), 6.3-6.4 (m, 2H), 6.38 (s, IH), 8.23 (d, IH, J = 9.3 Hz), 8.33 ( d, IH, J = 6.9 Hz) The present compound no. 1-262

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 1.20 (t, 3H, J = 7.3 Hz), 3.1-3.4 (m, 2H), 3.59 (q, 3H, J = 1.2 Hz), 4.0-4.3 (m, 2H), 4.3-4.4 (m, IH), 6.2-6.4 (m, 2H), 6.37 (s, IH), 7.2-7.4 (m, 5H), 8.19 (d, IH, J = 9.4 Hz), 8.49 ( d, IH, J = 6.8 Hz) The present compound no. 1-263

Η-NMR (CDC1₃₎ 300 MHz) δ (ppm): 3.55 (q, 3H, J = 1.1 Hz), 6.31 (s, IH), 6.3-6.4 (m, IH), 6.7-6.8 (m, IH), 7.2-7.3 (m, 3H), 7.4-7.5 (m, 2H), 8.2-8.3 (m, IH), 9.64 ( bs, IH)

The present compound no. 1-267 m.p.: 144.8°C

The present compound no. 1-268 m.p.: 162.2°C

The present compound no. 1-269 m.p.: 204.0°C The present compound no. 1-271 m.p.: 111.5°C

The present compound no. 1-274

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 2.62 (s, 6H), 3.60 (q, 3H, J = 1.2 Hz), 6.23 (dd, IH, J = 9.5, 2.9 Hz), 6.39 (s, IH), 7.25 (d, IH, J = 2.9 Hz), 8.13 (d, 1H, J = 9.5 Hz), 8.45 (bs, IH)

The present compound no. 1-276 m.p.: 172.7°C

The present compound no. 1-277 m.p.: 163.1°C

The present compound no. 1-278

Η-NMR (CDC1₃, 250 MHz) δ (ppm): 2.56 (s, 3H), 3.03 (s, 3H), 3.4- 3.5 (m, IH), 3.59 (m, 3H), 6.33 (dd, IH, J = 8.9, 2.6 Hz), 6.37 (s, IH), 6.73 (d, IH, J = 2.6 Hz), 7.49 (d, IH, J = 8.9 Hz)

The present compound no. 1-281 m.p.: 138.9°C

The present compound no. 1-285 m.p.: 162.5°C The present compound no. 1-287

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 2.90 (s, 6H), 3.59 (q, 3H, J = 1.3 Hz), 6.29 (dd, IH, J = 9.1, 2.6 Hz), 6.38 (s, IH), 6.75 (d, IH, J = 2.6 Hz), 7.83 (d, IH, J = 9.1 Hz)

The present compound no. 1-289 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 0.92 (t, 3H, J = 7.2 Hz), 1.2-1.4

(m, 2H), 1.6-1.7 (m, 2H), 2.82 (s, 3H), 3.17 (t, 2H, J = 7.3 Hz), 3.59 (q, 3H, J = 1.2 Hz), 6.29 (dd, IH, J = 8.9, 2.4 Hz), 6.37 (s, IH), 6.77 (d, IH, J = 2.4 Hz), 7.78 (d, IH, J = 8.9 Hz)

The present compound no. 1-290 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.14 (t, 6H, J = 7.1 Hz), 3.19 (q,

4H, J = 7.1 Hz), 3.59 (q, 3H, J = 1.2 Hz), 6.36 (dd, IH, J = 9.0, 2.5 Hz), 6.37 (s, IH), 6.83 (d, IH, J = 2.5 Hz), 7.73 (d, IH, J = 9.0 Hz)

The present compound no. 1-291

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 0.88 (t, 3H, J = 7.4 Hz), 1.13 (t, 3H, J = 7.1 Hz), 1.5-1.7 (m, 2H), 3.0-3.2 (m, 2H), 3.17 (q, 4H, J = 7.1 Hz), 3.59 (q, 3H, J = 1.2 Hz), 6.34 (dd, IH, J = 9.2, 2.8 Hz), 6.37 (s, IH), 6.83 (d, IH, J = 2.8 Hz), 7.74 (d, IH, J = 9.2 Hz)

The present compound no. 1-292 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 0.8-1.0 (m, 6H), 1.5-1.7 (m, 4H), 3.0-3.2 (m, 4H), 3.59 (q, 3H, J = 1.3 Hz), 6.33 (dd, IH, J = 9.2, 2.8 Hz), 6.37 (s, IH), 6.82 (d, IH, J = 2.8 Hz), 7.74 (d, IH, J = 9.2 Hz)

The present compound no. 1-589 Η-NMR (CDCI₃, 300 MHz) δ (ppm): 3.60 (q, 3H, J = 1.2 Hz), 6.40 (s,

IH), 6.85 (d, IH, J = 9.2 Hz), 7.78 (d, IH, J = 9.2 Hz)

Production Example 9

Step 1 Ammonia gas was bubbled into a mixture of 0.50 g of compound [1-g] and 3 ml of 2-methoxyethanol, foUowed by stirring at 120°C for 1 hour. The reaction mixture was cooled to room temperature and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 2 : 1) to give 0.14 g of compound [1-i] (the present compound no. I -199). m.p.: 179.7°C Step 2

First, 145 mg of ethyl 2-bromopropionate was added to 70 mg of compound [1-i], foUowed by stirring at 130°C for 2 hours and then refluxing for 4 hours. The reaction mixture was cooled to room temperature and then subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 3 : 1) to give 10 mg of compound [1-j] (the present compound no. 1-226). m.p.: 59.9°C Production Example 10

A mixture of 175 mg of compound [1-g], 39 mg of sodium thio- methoxide, and 1 ml of N,N-cbmethylformamide was stirred at 0°C to room temperature for 1 hour. The reaction mixture was poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate

= 3 : 1) to give 87 mg of compound [1-k] (the present compound no. 1-160). m.p.: 172.5°C

Production Example 11

A mixture of 175 mg of compound [1-g], 74 mg of ethyl 2-mercapto- propionate, 83 mg of potassium carbonate, and 1 ml of N,N-dimethyl- formamide was stirred at 60°C for 3 hours. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chroma- tography (eluent, hexane : ethyl acetate = 3.5 : 1) to give 77 mg of compound [1-1] (the present compound no. 1-179).

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 1.2-1.4 (m, 3H), 1.58 (d, 3H, J = 7.4 Hz), 3.61 (q, 3H, J = 1.3 Hz), 3.77 (q, IH, J = 7.4 Hz), 4.0-4.2 (m, 2H), 6.38 (s, IH), 7.04 (dd, IH, J = 9.3, 2.8 Hz), 7.30 (d, IH, J = 2.8 Hz), 8.29 (d, IH, J = 9.3 Hz)

Production Example 12

Step 1 To a mixture of 12.9 g of compound [4-b], 17 ml of tetrahydrofuran, and 50 ml of methylene chloride was added dropwise 4.0 ml of 32% peracetic acid at 0°C. Then, 2.98 g of copper (II) acetate and 3.29 g of compound [1-a] were added thereto, foUowed by warming to 60°C and then stirring for 1 hour. The reaction mixture was cooled to 0°C. Saturated aqueous sodium hydro gensulfite solution and IN hydrochloric acid were added thereto, foUowed by filtration through CeHte. The filtrate was extracted with ethyl acetate and then concentrated. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) and the crystals obtained were washed with hexane to give 0.67 g of compound [1-m]. Η-NMR (CDCI₃, 300 MHz) δ (ppm): 0.20 (s, 6H), 0.97 (s, 9H), 3.56- 3.57 (m, 3H), 6.34 (s, IH), 6.60-6.64 (m, 3H), 7.13-7.18 (m, IH)

Step 2

A mixture of 0.57 g of compound [1-m], 0.08 g of potassium fluoride, and 3 ml of N.N-dimethyHormamide was stirred at room temperature for 1 hour. Water and 1 N hydrochloric acid were added thereto in this order, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) to give 0.30 g of compound [1-n] (the present compound no. 1-599). m.p.: 191.3°C

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 3.57-3.58 (m, 3H), 5.02 (s, IH), 6.36 (s, IH), 6.55-6.65 (m, 3H), 7.15-7.21 (m,lH)

Step 3

A mixture of 0.12 g of compound [1-n], 90 mg of ethyl 2-bromo- propionate, 60 mg of potassium carbonate, and 2 ml of N,N-dimethylform- amide was stirred at room temperature for 2 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) to give 0.10 g of compound [l-o] (the present compound no. 1-625).

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 1.25 (t, 3H, J = 7.1), 1.59 (d, 3H, J = 6.9), 3.55-3.57 (m, 3H), 4.21 (q, 2H, J = 7.1), 4.73 (q, IH, J = 6.9), 6.33 (s, IH), 6.60-6.63 (m, 2H), 6.68-6.72 (m, IH), 7.19-7.25 (m, IH) Production Example 13

Step 1

To a mixture of 10.51 g of compound [4-c], 10 ml of tetrahydrofuran, and 30 ml of methylene chloride was added dropwise 2.9 ml of 32% peracetic acid at 0°C. Then, 2.15 g of copper (II) acetate and 2.36 g of compound [1-a] were added thereto, foUowed by stirring at 50°C for 1 hour. The reaction mixture was cooled to 0°C. Saturated aqueous sodium hydrogensulfite solution and IN hydrochloric acid were added thereto, foUowed by filtration through CeHte. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) to give 0.40 g of compound [1-p].

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 0.23 (s, 6H), 1.02 (s, 9H), 3.56- 3.57 (m, 3H), 6.34 (s, IH), 6.60 (dd, IH, J = 8.7, 2.9 Hz), 6.74 (d, IH, J = 2.9 Hz), 7.26 (d, IH, J = 8.7 Hz) Step 2

A mixture of 0.40 g of compound [1-p], 0.05 g of potassium fluoride, and 2 ml of N,N-dimethylformamide was stirred at room temperature for 1.5 hours. Water and IN hydrochloric acid were added thereto in this order, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 4 : 1) to give 0.25 g of compound [1-q] (the present compound no. 1-350).

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 3.55-3.57 (m, 3H), 5.63 (s, IH), 6.35 (s, IH), 6.66 (dd, IH, J = 8.6, 2.9 Hz), 6.72 (d, IH, J = 2.9 Hz), 7.27 (d, IH, J = 8.6 Hz)

Step 3 A mixture of 0.40 g of compound [1-q], 0.07 g of potassium carbonate,

0.10 g of ethyl 2-bromopropionate, and 2 ml of N,N-dimethylformamide was stirred at room temperature for 2 hours. Water was added thereto, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 3 : 1) to give 0.19 g of compound [1-r] (the present compound no. 1-377). m.p.: 102.3°C Production Example 14

Step 1

A mixture of 0.10 g of compound [1-n] and 1 ml of sulfuryl chloride was stirred at room temperature for 3 hours. Water was added thereto, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to give 0.10 g of compound [1-s].

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 3.56-3.58 (m, 3H), 6.34 (s, IH), 6.53 (s, IH), 7.41 (s, IH) Step 2

A mixture of 0.09 g of compound [1-s], 0.04 g of potassium carbonate, 0.05 g of ethyl 2-bromopropionate, and 2 ml of N,N-dimethylformamide was stirred at room temperature for 2 hours. Water was added thereto, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 3 : 1) to give 50 mg of compound [1-t] (the present compound no. 1-671).

Η-NMR (CDC1₃, 300 MHz) δ (ppm): 1.20 (t, 3H, J = 7.1), 1.62 (d, 3H, J = 6.7), 3.55-3.57 (m, 3H), 4.13 (q, 2H, J = 7.1), 4.59 (q, IH, J = 6.7), 6.35 (s, IH), 6.49 (s, IH), 7.45 (s, IH)

For one compound produced by the same producing process as described in Production Example 14, its present compound number and physical properties are shown below. The present compound no. 1-645 m.p.: 123.4°C Production Example 15

A mixture of compound [15-a], methyl iodide, potassium carbonate, and dimethylsulfoxide is heated with stirring. The reaction mixture is cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue is subjected to sflica gel column chromatography to give compound [1-e] (the present compound no. 1-4).

The foUowing wfll describe a production example for the present intermediate A.

Production Example Al

Step 1

A mixture of 2,3-dichlorophenol, 0-(2,4-dinitrophenyl)hydroxylamine, potassium carbonate, and N,N-dimethylformamide is heated with stirring. The reaction mixture is cooled and then poured into water, foUowed by extraction with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and then concentrated. The residue is subjected to sflica gel column chromatography to give 0-(2,3-dichlorophenyl)hydroxy- amine. Step 2

Pyridine is added dropwise to a mixture of 0-(2,3-dichlorophenyl)- hydroxyamine, phenyl chloroformate, and tetrahydrofuran, foUowed by stirring at room temperature. Diluted hydrochloric acid is added to the reaction mixture, foUowed by extraction with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and then concentrated. The residue is subjected to silica gel column chromatography to give N-phenyloxycarbonyl-0-(2,3-dicMorophenyl)hydroxyamine.

Step 3 Sodium hydride is added to N,N-dimethylformamide, to which ethyl

3-amino-4,4,4-trifluorocrotonate is then added dropwise. At room temperature, N-ethyloxycarbonyl-0-(2,3-oHcMorophenyl)hyd^oxyarαine dissolved in N,N-dimethylformamide is added dropwise thereto, foUowed by heating with stirring. The reaction mixture is poured into ice-water, and diluted hydro- chloric acid is added thereto, foUowed by extraction with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate and then concentrated. The residue is subjected to sflica gel column chromatography to give compound [15-a].

The foUowing wiU describe production examples for the present intermediate B.

Production Example Bl

Step 1

To 10.5 g of ethyl 3-amino-4,4,4-trifluorocrotonate were added 50 ml of N,N-dimethylformamide and 2.10 g of sodium hydride. The reaction mixture was stirred at 0°C for 30 minutes, and a mixture of 11.6 g of N-phenyloxycarbonyl-0-benzy ydroxylamine and 10 ml of N,N-dimethyl- formamide was added thereto, foUowed by stirring at 80°C for 2 hours. The reaction mixture was cooled to room temperature, and 3.56 ml of methyl iodide was added thereto, foUowed by stirring at 60°C for 1 hour. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : ethyl acetate = 5 : 1) to give 12.5 g of 3-benzyloxy- l-methyl-6-trifluoromethyl-2,4(lH,3H -pyrimidinedione.

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 3.52 (q, 3H, J = 1.3 Hz), 5.14 (s, 2H), 6.25 (s, IH), 7.3-7.4 (m, 3 Hz), 7.5-7.6 (m, 2 Hz) Step 2

To 150 mg of 3-benzyloxy- l-methyl-6-trifluoromethyl-2,4(lH,3H)- pyrimidinedione were added 2.5 ml of methanol and 19 mg of 10% paUadium/carbon. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen gas for 1 hour. The atmosphere over the reaction system was replaced with nitrogen gas. The reaction mixture was then filtered through Cehte. The filtrate was concentrated to give 100 mg of compound [1-a].

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 3.57 (s, 3H), 6.32 (s, IH)

Production Example B2 Step 1

To 41 g of ethyl 3-amino-4,4,4-trifluorocrotonate were added 100 ml of N,N-dimethylformamide and 8.4 g of sodium hydride. The reaction mixture was stirred at 0°C for 30 minutes. A mixture of 55 g of N-phenyl- oxycarbonyl-0-benzyUiydroxyamine and 10 ml of N,N-dimethylformamide was added thereto, foUowed by stirring at 60°C for 2 hours. The reaction mixture was cooled to room temperature and then poured into a mixture of acetic acid and ice-water. The deposited crystals were coUected by filtration to give 10 g of 3-benzyloxy-6-trifluoromethyl-2,4(lH,3H)-pyrir dinedione.

Η-NMR (CDClg, 300 MHz) δ (ppm): 5.07 (s, 2H), 6.12 (s, IH), 7.3- 7.4 (m, 3 Hz), 7.4-7.5 (m, 2 Hz)

Step 2

To 1.0 g of 3-benzyloxy-6-trifluoromethyl-2,4(lH,3H)-pyrimidine- dione were 7.0 ml of N,N-dimethylformamide and 0.14 g of sodium hydride. The reaction mixture was stirred at 0°C for 30 minutes. Then, 0.70 g of 0-(2,4-dinitrophenyl)hydroxylamine was added thereto, foUowed by stirring at 60°C for 1 hour. The reaction mixture was cooled to room temperature and then poured into water, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sflica gel column chromatography (eluent, hexane : tetrahydrofuran = 5 : 1) to give 0.69 g of 3-benzyloxy- l-amino-6-trifluoromethyl- 2,4(lH,3H)-pyrimidinedione. Η-NMR (CDClg, 300 MHz) δ (ppm): 4.58 (s, 2H), 5.15 (s, 2H), 6.18

(s, IH), 7.4-7.5 (m, 3 Hz), 7.5-7.6 (m, 2 Hz)

Step 3

To 690 mg of 3-benzyloxy- l-amino-6-trifluoromethyl-2,4(lH,3H)- pyrimidinedione were added 12 ml of methanol, 12 ml of tetrahydrofuran, and 89 mg of 20% paUadium/carbon. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen gas for 1 hour. The atmosphere over the reaction system was replaced with nitrogen gas. The reaction mixture was then filtered through CeHte. The filtrate was concentrated to give 309 mg of compound [2-a]. m.p., 89.7°C

Η-NMR (CDCI₃, 300 MHz) δ (ppm): 4.68 (s, 2H), 6.28 (s, IH)

Production Example B3

To 0.76 g of 3-benzyloxy-6-trifluoromethyl-2,4-(lH,3H)-pyrimidine- dione were added 30 ml of methanol and 80 mg of 20% paUadium/carbon. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen gas for 1.5 hours. The atmosphere over the reaction system was replaced with nitrogen gas. The reaction mixture was then filtered through CeHte. The filtrate was concentrated to give 0.51 g of 3-hydroxy-6- trifluoromethyl-2,4-(lH,3H)-pyrimidinedione.

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 6.07 (s, IH)

The foUowing wfll describe production examples for intermediates used for the production of the present compounds, as reference production examples.

Reference Production Example 1

Step 1

To a mixture of 25 g of compound [Cl-a], 12.5 ml of ethyl chloro- formate, and 200 ml of tetrahydrofuran was added dropwise 40 ml of pyridine. The reaction mixture was stirred at room temperature for 1 hour.

Diluted hydrochloric acid was added thereto, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated to give 33 g of the crude compound [Cl-b]. Steps 2 and 3 To 300 ml of N,N-dimethylformamide was added 5.9 g of sodium hydride and then added dropwise 26.8 g of ethyl 3-amino-4,4,4-trifluoro- crotonate. The reaction mixture was stirred at room temperature for 10 minutes, and 33 g of the crude compound [Cl-b] suspended in 200 ml of N,N-dimethylformamide was added dropwise thereto, foUowed by stirring at 100°C for 1 hour and then at 160°C for 1.5 hours. After cooling for 30 minutes, 9.1 ml of methyl iodide was added, and the reaction mixture was left at room temperature overnight. Another 2 ml of methyl iodide was added thereto, foUowed by stirring at room temperature for 3 hours. The reaction mixture was poured into ice-water, and diluted hydrochloric acid was added thereto, foUowed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was washed with t-butyl methyl ether and then with hexane to give 19.9 g of compound [Cl-d]. m.p.: 156.8°C Step 4

A mixture of 50 ml of acetic acid, 50 ml of water, and 5.0 g of iron powder was heated to 80°C, to which a solution of 5.0 g of compound [Cl-d] in 45 ml of ethyl acetate was added dropwise. After completion of the drop- wise addition, heating was ceased, and the reaction mixture was then stirred for 1 hour. Water was added to the reaction mixture, foUowed by extraction with ethyl acetate. The organic layer was washed with water and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was washed with t-butyl methyl ether and then with hexane to give 1.0 g of compound [Cl-e]. The wash filtrate was concentrated and then subjected to column chromatography (eluent, hexane : ethyl acetate = 2 : 1) to give another 1.9 g of compound [3-a]. Yield: 36%. Η-NMR (CDC1₃, 300 MHz) δ (ppm): 3.49-3.51 (m, 3H), 6.22 (s, IH),

9.40 (br, IH)

Reference Production Example 2

To a mixture of 2.79 g of magnesium, 10 ml of diethyl ether, and a piece of iodine was added dropwise a mixture of 20.0 g of compound [4-d] and

45 ml of diethyl ether at room temperature at such a speed that the reaction mixture was gently refluxed. Then, 20 ml of diethyl ether was added thereto, foUowed by stirring at room temperature for another 1 hour. Then,

50 ml of benzene was added thereto, and 8.6 g of bismuth trichloride was added thereto in five portions over 30 minutes, foUowed by heating under reflux for 4.5 hours. The reaction mixture was cooled to 0°C, and a saturated aqueous ammonium chloride solution was added thereto, foUowed by filtration through CeHte. The filtrate was extracted with t-butyl methyl ether. The organic layer was washed with saturated sodium chloride solu- tion, dried over anhydrous sodium sulfate, and then concentrated. The residue was washed with hexane to give 7.67 g of compound [4-a].

Η-NMR (CDCI₃, 250 MHz) δ (ppm): 7.33-7.38 (m, 6H), 7.58-7.63 (m, 6H)

Some of the present compounds are fllustrated below; however, the present compounds are not Hmited to these examples.

In the foUowing structural formulas I to XVI, R⁵, R⁶, R⁷, and R⁸ are those as shown in Tables 1 to 30.

π

V VI

VII VIII

DC X

XI XII

XV XVI TABLE 1

TABLE 2

TABLE 3

TABLE 4

TABLE 5

TABLE 6

TABLE 7

TABLE 8

TABLE 9

TABLE 10

TABLE 11

TABLE 12

TABLE 13

TABLE 14

TABLE 15

TABLE 16

TABLE 17

TABLE 18

TABLE 19

TABLE 20

TABLE 21

TABLE 22

TABLE 23

TABLE 24

TABLE 25

TABLE 26

TABLE 27

TABLE 28

TABLE 29

TABLE 30

In Tables 1 to 30, the superscripts "n", "I", and "c" mean the prefixes "normal-", "iso-", and "cyclo-", respectively.

In the foUowing structural formula XVII, R², R⁴, R⁵, R⁶, R⁷, and R⁸ are those as shown in Tables 31 and 32.

XVII as

O 0 ffi a a X a a a a a a a X a a a X a a a a a a a a a

O fa 2 o fa 2 o fa 2 o

K a o 2 O o a a a o 2 o o a a a O 2 O o a a a o 2

ft! a ϋ a X a a o a o a a a a O a o a a a a ϋ a o a a

rH O o O U o o ϋ fa o o o o o o fa o o O o o o fa o o o o

CM

o o o o o o o o ϋ o o ϋ o ϋ o o o o o o o o o o o

a a a o X o o a o o a o o a o a o a o a o o a o a a o 2

CN 00 «o ΪD t 00 05 o CN CO Ui ςo c- 00 OS o CN co in CN J CN CN CN o

©

O

TABLE 32

The foUowing wiU describe formulation examples. In these formulation examples, the present compounds are designated by their compound numbers {i.e., chemical formula number - sub-group number) and parts are by weight.

Formulation Example 1

Fifty parts of each of the present compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-258, 1-263, 1-267, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-351, 1-377, 1-585, 1-645, and 11-89, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrated silicon oxide are weU pulverized and mixed to give a wettable powder for each compound.

Formulation Example 2

Ten parts of each of the present compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-258, 1-263, 1-267, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-351, 1-377, 1-585, 1-645, and 11-89, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cylcohexanone are weU mixed to give an emulsifiable concentrate for each compound. Formulation Example 3

Two parts of each of the present compounds 1-1 to 1-736, II-l to 11-736, III-l to III-736, rV-1 to rV-736, V-l to V-736, VI-1 to VI-736, VII-1 to VII-736, VIII- 1 to Vπi-736, IX-l to IX- 736, X-l to X-736, XI- 1 to XI-736, XII- 1 to XII- 736, XIII- 1 to XIII-736, XIV- 1 to XTV-736, XV- 1 to XV-736, XVI-1 to XVI-736, and XVII- 1 to XVTI-28, 2 parts of synthetic hydrated silicon oxide, 2 parts of calcium Hgnin sulfonate, 30 parts of bentonite, and 64 parts of kaolin clay are weU pulverized and mixed, and the mixture is weU kneaded with water, followed by granulation and drying, to give a granule for each compound. Formulation Example 4

Twenty-five parts of each of the present compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-258, 1-263, 1-267, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-351, 1-377, 1-585, 1-645, and 11-89, 50 parts of 10% aqueous polyvinyl alcohol solution, and 25 parts of water are mixed and pulverized until the mean particle size reaches 5 μm or smaller to give a flowable for each compound.

Formulation Example 5 Five parts of each of the present compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-85,

1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-258, 1-263, 1-267, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-351, 1-377, 1-585, 1-645, and 11-89 is added to 40 parts of 10% aqueous polyvinyl alcohol solution, and the mixture is emulsified by dispersion with a homogenizer until the mean particle size reaches 10 μm or smaUer, foUowed by addition of 55 parts of water, to give a concentrated emulsion for each compound. The foUowing are test examples for demonstrating that the present compounds are useful as the active ingredients of herbicides. In these test examples, the present compounds are designated by their compound numbers defined above. Test Example 1

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with soil, seeded with velvetleaf {Abutilon theophrasti), and kept in a greenhouse for 7 days. After that, according to Formulation Example 2, test compound 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-134, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-251, 1-253, 1-258, 1-259, 1-262, 1-263, 1-267, 1-268, 1-269, 1-271, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-350, 1-351, 1-377, 1-585, 1-587, 1-625, 1-645, 1-671, 1-694, or 11 -89 was formulated into an emulsifiable concentrate, which was diluted in a prescribed amount with water containing a spreading agent and then uniformly sprayed over the fohage of the plants with a sprayer at a ratio of 1000 liters per hectare. The pots were further kept in the greenhouse for 13 days and examined for herbicidal activity. As a result, it was found that compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1- 106, 1-108, 1- 115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-134, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-251, 1-253, 1-258, 1-259, 1-262, 1-263, 1-267, 1-268, 1-269, 1-271, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-350, 1-351, 1-377, 1-585, 1-587, 1-625, 1-645, 1-671, 1-694, and π -89 completely killed the velvetleaf each at a dosage of 2000 g/ha.

Test Example 2

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were fiUed with soU and seeded with velvetleaf {Abutilon theophrasti). According to Formulation Example 2, test compound 1-3, 1-4, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-134, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-267, 1-268, 1-271, 1-274, 1-276, 1-277, 1-278, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-350, 1-351, 1-377, 1-585, 1-625, or π -89 was formulated into an emulsifiable concentrate, which was diluted in a prescribed amount with water and then uniformly sprayed over the surface of the soil in the pots with a sprayer at a ratio of 1000 liters per hectare. The pots were kept in a greenhouse for 13 days and examined for herbicidal activity. As a result, it was found that compounds 1-3, 1-4, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-134, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-267, 1-268, 1-271, 1-274, 1-276, 1-277, 1-278, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-350, 1-351, 1-377, 1-585, 1-625, and π -89 completely inhibited the germination of the velvetleaf each at a dosage of 2000 g/ha. Test Example 3 Cylindrical plastic pots of 9 cm in diameter and 11 cm of depth were filled with soil, seeded with barnyardgrass {Echinochloa oryzicola), flooded into a paddy field, and kept in a greenhouse for 12 days. According to Formulation Example 2, test compound 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-160, 1- 179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-258, 1-263, 1-267, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-351, 1-377, 1-585, 1-645, or H -89 was formulated into an emulsifiable concentrate, which was d luted in a prescribed amount with water and then appHed on the water surface in the pots at a ratio of 50 liters per are. The pots were further kept in the greenhouse for 13 days and examined for herbicidal activity. As a result, it was found that compounds 1-3, 1-4, 1-5, 1-7, 1-8, 1-85, 1-87, 1-88, 1-89, 1-91, 1-105, 1-106, 1-108, 1-115, 1-116, 1-118, 1-123, 1-126, 1-127, 1-160, 1-179, 1-199, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-214, 1-220, 1-221, 1-226, 1-246, 1-249, 1-253, 1-258, 1-263, 1-267, 1-274, 1-276, 1-277, 1-278, 1-281, 1-285, 1-287, 1-289, 1-290, 1-291, 1-292, 1-301, 1-351, 1-377, 1-585, 1-645, and H -89 completely killed the barnyardgrass each at a dosage of 1000 g/ha.

Industrial Apphcability

The uracil compounds of the present invention are useful as active ingredients of herbicides because of their exceUent herbicidal activity.

Claims

1. A uracil compound of the general formula:

wherein R¹ is hydrogen, halogen, cyano, or C_j-Cg alkyl;

R² is C_x-C₃ alkyl, C_rC₃ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, N(R⁶¹)R⁶², or N=C(R⁶¹)R⁶², wherein R⁶¹ and R⁶² are the same or different and independently hydrogen, C_j-Cg alkyl, or Ci-Cg haloalkyl; R³ is C_rC₃ alkyl or C_rC₃ haloalkyl; or R² and R³ may be combined at their ends to form optionaUy fluorine- substituted trimethylene or optionaUy fluorine-substituted tetramethylene; Q is optionaUy substituted phenyl; and

X, Y, and Z are the same or different and independently oxygen or sulfur.

2. The uracil compound according to claim 1, wherein Q is a group of the general formula:

wherein R⁴ is hydrogen, halogen, Cj-Cg alkyl, or d-Cg haloalkyl;

R⁵ is hydrogen, halogen, N0₂, CN, C^C_a alkoxy, d-Cg alkyl, or C_rC₃ haloalkyl;

R⁶ is hydrogen, halogen, C C₆ alkyl, C_rC₆ haloaUcyl, OR⁹, SR¹⁰, N(R^U)R¹², COOR¹³, COOM, COR¹⁴, SO₂R¹⁵, NO₂, CN, CR²⁰=C(R¹⁶)R¹⁷, or CR¹⁸=NOR¹⁹;

R⁷ is hydrogen, halogen, Ci-C₆ alkyl, C_ι-C₆ haloaUcyl, hydroxy C_ι-C₆ alkyl, d-Cβ alkoxy C_rC₆ alkyl, OR³⁹, SR⁴⁰, N(R⁴¹)R⁴², COOR⁴³, COOM, COR⁴⁴,

SO₂R⁴⁵, NO₂₎ CN, C ^COHR⁴⁷, or CR⁴⁸=NOR⁴⁹; and R⁸ is hydrogen, halogen, Ci-C₆ alkyl, Cι-C₆ haloaUcyl, hydroxy C_j-Ce aUcyl, C_rC₆ aUcoxy C_x-C₆ aUcyl, OR⁶⁹, SR⁷⁰, N(R⁷¹)R⁷², NR⁷¹N(R⁷⁰)R⁷²,

CR⁷⁸=NOR⁷⁹; wherein R⁹, R³⁹, and R⁶⁹ are the same or different and independently hydrogen, C_ι-C₁₀ alkyl, C C₁₀ haloalkyl, C₃-C₈ alkenyl, C₃-C₈ haloalkenyl, Cg-Cg alkynyl, C₃-C₈ haloalkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkenyl, C₃-C₁₀ cycloalkyl

alkyl, C₃-C₁₀ halocycloalkyl Ci-Cg alkyl, C₃-C_ι0 cycloalkenyl C_ι-C₃ alkyl, C₃-Cι₀ halocycloalkenyl Ci-Cg alkyl, (Cι-C₅ allcyl)carbonyl, (Cj-Cg haloaUcyl)carbonyl, (C₃-C₆ cycloalkyl)carbonyl,

(C₃-C₆ halocycloalkyl)carbonyl, (Ci-C₆ alkyl)carbonyl Cι-C₆ alkyl, (Ci-C₆ haloalkyl)carbonyl Ci-C₆ alkyl, (Cι-C₆ alkoxy)carbonyl, (C_ι-C₆ haloalkoxy)carbonyl, (C₃-C_ι0 cycloaUcoxy)carbonyl, (C₃-C₁₀ halocyclo- alkoxy)carbonyl, carboxy C_ι-C₅ aUcyl, (hydroxy Ci-C₅ alkoxy)carbonyl Ci-C₅ aUcyl, (Cι-C_ι0 aUcoxy)carbonyl C_ι-C₅ alkyl, (C_ι-C₁₀ haloaUcoxy)- carbonyl Ci-C₅ alkyl, tetrahydrofuranyloxycarbonyl Ci-C₆ alkyl, tetrahydropyranyloxycarbonyl Ci-C₆ aUcyl, {(Ci-C₆ aUcoxy) Ci-C₆ aUcoxy}carbonyl C_ι-C₆ alkyl, [{(C_ι-C₆ alkoxy)carbonyl} Ci-C₆ alkoxy]- carbonyl Ci-C₆ aUcyl, [2-aza-2-(C_ι-C₃ alkoxy)- l-{(C_rC₃ alkoxy)- carbonyl} vinyl] C_ι-C₃ alkyl, (C₃-Cι₀ cycloalkoxy)carbonyl Ci-C_e alkyl,

(C₃-C₁₀ halocycloaUcoxy)carbonyl Cι-C₃ alkyl, aminocarbonyl C_ι-C₆ aUcyl, (Ci-C₆ aUcylamino)carbonyl C_ι-C₆ alkyl, (C₃-C₈ alkenyloxy)- carbonyl Ci-C₆ alkyl, (C₃-C₈ aUcynyloxy)carbonyl C_ι-C₆ aUcyl, hydroxy C_rC₆ alkyl, C_rC₆ aUcoxy C_ι-C₆ alkyl, Ci-C₆ haloaUcoxy Ci-C₆ aUcyl, mercapto C_ι-C₆ a cyl, C_ι-C₆ alkylthio C_ι-C₆ alkyl, Ci-C₆ haloalkylthio C_ι-C₆ alkyl, cyano C_ι-C₄ aUcyl, tetrahydrofuranyl, tetrahydropyranyl, optionaUy substituted phenyl, (optionaUy substituted phenyl) C_ι-C₃ alkyl, optionaUy substituted phenylcarbonyl, or SO₂R²²;

R¹⁰, R⁴⁰, and R⁷⁰ are the same or different and independently hydrogen, C_ι-C₁₀ alkyl, C_ι-C_ι0 haloalkyl, C₃-C₈ alkenyl, C₃-C₈ haloalkenyl, C₃-C₈ alkynyl, C₃-C₈ haloalkynyl, C₃-C₁₀ cycloalkyl, C₃-Cι₀ halocycloalkyl, C₃-C_ι0 cycloalkenyl, C₃-C₁₀ halocycloalkenyl, C₃-C₁₀ cycloalkyl Cj-Cg alkyl, C₃-C_ι0 halocycloalkyl Cj-Cg alkyl, C₃-C_ι0 cycloalkenyl C_ι-C₃ alkyl, C₃-C_ι0 halocycloalkenyl Cj-Cg alkyl, (Ci-C₅ alkyl)carbonyl, (C_ι-C₅ haloaUcyl)carbonyl, (C₃-C₆ cycloalkyl)carbonyl, (C₃-C₆ halocycloalkyl)carbonyl, (Ci-C₆ alkyl)carbonyl Ci-C₆ alkyl, (Cι-C₆ haloalkyl)carbonyl C_ι-C₆ alkyl, (C_ι-C₆ alkoxy)carbonyl, (Ci-C₆ haloaUcoxy)carbonyl, (C₃-C_ι0 cycloalkoxy)carbonyl, (C₃-C_ι0 halocyclo- alkoxy)carbonyl, carboxy C_ι-C₅ aUcyl, (hydroxy Cj-Cg aUcoxy)carbonyl C_ι-C₅ aUcyl, (Cj-Ci_o alkoxy)carbonyl C_ι-C₅ alkyl, (Cι-C₁₀ haloalkoxy)- carbonyl C_j-Cg alkyl, {(C_ι-C₆ alkoxy) Ci-C₆ alkoxy}carbonyl C_rC₆ alkyl, (C₃-C_ι0 cycloalkoxy)carbonyl Ci-C₅ alkyl, (C₃-C_ι0 halocyclo- alkoxy)carbonyl Ci-Cg alkyl, aminocarbonyl C_ι-C₆ aUcyl, (Cι-C₆ aUcyl- amino)carbonyl C_ι-C₆ alkyl, hydroxy Cj-Cg alkyl, Ci-Cg alkoxy Ci-C₆ alkyl, C_ι-C₆ haloalkoxy Ci-Cg alkyl, mercapto C_ι-C₆ alkyl, C_ι-C₆ alkylthio C_ι-C₆ alkyl, Cj-Cg haloalkylthio Ci-Cg alkyl, cyano C C₄ alkyl, tetrahydrofuranyl, tetrahydropyranyl, optionaUy substituted phenyl, (optionally substituted phenyl) Ci-C₃ alkyl, or optionally substituted phenylcarbonyl;

R¹¹, R¹², R⁴¹, R⁴², R⁷¹, and R⁷² are the same or different and independently hydrogen, d-Ci_o alkyl, C_J-C_K, haloaUcyl, C₃-C₈ alkenyl, C₃-C₈ haloalkenyl, C₃-C₈ alkynyl, C₃-C₈ haloalkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkenyl, C₃-C₁₀ cycloalkyl C_rC₃ aUcyl, C₃-C₁₀ halocycloaUcyl Cj-Cg alkyl, C₃-C₁₀ cycloalkenyl Cj-Oj alkyl, C₃-C₁₀ halocycloalkenyl Cj-Cg alkyl, (C^C_g aUcyl)carbonyl, (C_rC₅ haloalkyl)carbonyl, (C₃-C₆ cycloalkyl)carbonyl,

(C₃-Cg halocycloalkyl)carbonyl,

alkyl) carbonyl

alkyl, (Cj-Cg haloalkyl)carbonyl C_rC₆ alkyl, (C_rC₆ alkoxy)carbonyl, (d-Cg haloaUcoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃-C₁₀ halocyclo- aUcoxy)carbonyl, carboxy Cj-C₃ aUcyl, (hydroxy C Cg aUcoxy)carbonyl C_rC₅ aUcyl, (C_rC₁₀ alkoxy)carbonyl C_rC₅ alkyl, (C_rC₁₀ haloalkoxy)- carbonyl

alkyl, (C₃-C₁₀ cycloalkoxy)carbonyl Cj-Cg alkyl, (C₃-C₁₀ halocycloaUcoxy)carbonyl Cj-Cg alkyl, aminocarbonyl

alkyl, (Cj-Cg alkylamino)carbonyl

alkyl, hydroxy Cj-Cg alkyl, C_j-Cg alkoxy Cj-Cg alkyl, C_rC₆ haloalkoxy Cj-Cg alkyl, mercapto

aUcyl, {(C Cg alkoxy) C_rC₆ alkoxy} carbonyl Ci-Cg alkyl, C_ι-C₆ alkylthio

Ci-Cg alkyl, C_rC₆ haloaUcylthio Cι-C₆ alkyl, cyano C_ι-C₄ aUcyl, optionaUy substituted phenyl, (optionaUy substituted phenyl) C_ι-C₃ alkyl, (optionaUy substituted

alkoxy)carbonyl) C_j-Cg alkyl, optionally substituted phenylcarbonyl, SR³⁴, SOR²¹, or SO₂R²²; R¹³, R⁴³, and R⁷³ are the same or different and independently hydrogen, C^C^ alkyl, C_J-C_JO haloalkyl, C₃-C₁₀ alkenyl, C₃-C₁₀ haloalkenyl, C₃-C₁₀ alkynyl, C₃-C₁₀ haloalkynyl, C₃-C₈ cycloaUcyl, C₃-C₈ halocycloalkyl, N(R²³)R²⁴, N=C(R²³)R²⁴, tetrahydrofuranyl, tetrahydropyranyl, carboxy Cj-C₃ aUcyl, (C₃-C₈ cycloalkoxy)carbonyl Cj-C₃ alkyl, (C₃-C₈ alkenyloxy)carbonyl

alkyl, (C₃-C₈ alkynyloxy)- carbonyl Ci-Cg alkyl, tetrahydrofuranyloxycarbonyl Cj-Cg alkyl, tetrahydropyranyloxycarbonyl Cj-Cg alkyl, (Cj-C₃ alkoxy)carbonyl Ci-Cg aUcyl, or (C^C_s haloalkoxy)carbonyl Cj-Cg aUcyl; R¹⁴, R⁴⁴, and R⁷⁴ are the same or different and independently hydrogen, chlorine, Cj-Cs alkyl, C_rCg haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloaUcyl, or N(R²⁵)R²⁶;

R¹⁵, R⁴⁵, and R⁷⁵ are the same or different and independently chlorine, C_rC₁₀ alkyl, C C₁₀ haloaUcyl, N(R²⁷)R²⁸, or OR²⁹;

R¹⁶, R⁴⁶, and R⁷⁶ are the same or different and independently hydrogen, halogen, or C^ , alkyl;

R¹⁷, R⁴⁷, and R⁷⁷ are the same or different and independently hydrogen, COOR³⁰, cyano, or Ci-Cg alkyl; R¹⁸, R⁴⁸, and R⁷⁸ are the same or different and independently hydrogen, C_x-C₄ alkyl, C_x-C₄ haloaUcyl, C₃-C₆ cycloaUcyl, or C₃-C₆ halocycloalkyl;

R¹⁹, R⁴⁹, and R⁷⁹ are the same or different and independently hydrogen, C_x-C₁₀ alkyl, C_x-C_xo haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halo- cycloalkyl, C₃-C₁₀ cycloaUcyl C_x-C₃ alkyl, C₃-C₁₀ halocycloalkyl C_x-C₃ alkyl, C₃-C₅ alkenyl, C₃-C₅ haloalkenyl, C₃-C₆ alkynyl, C₃-Cg haloalkynyl, carboxy C_x-C₃ alkyl, (Ci-Cg alkoxy)carbonyl C_x-C₃ alkyl, (Cj-C₅ haloalkoxy)carbonyl C_x-C₃ aUcyl, optionaUy substituted phenyl, or (optionaUy substituted phenyl) C_x-C₃ alkyl; R²⁰, R⁵⁰, and R⁸⁰ are the same or different and independently hydrogen, chlorine, Cj-Cg alkyl, C_x-C₅ haloalkyl, C₃-C₆ cycloaUcyl, or C₃-C₆ halocycloaUcyl; and

M is an alkaU metal; wherein R³⁴ is C_x-C₁₀ alkyl, C_x-C₁₀ haloalkyl, or optionaUy substituted phenyl;

R²¹ is C_x-C_x0 aUcyl, C_x-C_x0 haloaUcyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloaUcyl, or optionaUy substituted phenyl;

R²² is C_x-C_xo alkyl, C₁-C₁₀ haloaUcyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloaUcyl, or optionaUy substituted phenyl;

R²³ is hydrogen or C_x-Cg alkyl;

R²⁴ is hydrogen, C_x-C₅ alkyl, C_x-C₅ haloaUcyl or optionaUy substituted phenyl; R²⁵ is hydrogen, C_x-C₁₀ alkyl, C_x-C₁₀ haloalkyl, SO₂H,

C_x-C₅ alkylsulfonyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloaUcyl, carboxy C_x-C₃ alkyl, (C_x-C₅ alkoxy)carbonyl C_x-C₃ alkyl, optionaUy substituted phenyl, C_x-C₁₀ aUcylsulfinyl, C₁-C₁₀ haloaUcylsurfinyl, C₃-C₈ cycloalkylsulfinyl, C₃-C₈ halocyclo- aUcylsulfinyl, optionaUy substituted phenylsulfinyl, C_x-C₁₀ alkylsulfonyl, C_x-C₁₀ haloalkylsulfonyl, C₃-C₈ cycloalkyl- sulfonyl, C₃-C₈ halocycloaUcylsulfonyl, or optionaUy substituted phenylsulfonyl;

R²⁶ is hydrogen, C_x-C_x0 aUcyl, or C_x-C_xo haloalkyl; R²⁷ is hydrogen, C_x-C₅ alkyl, or C_x-C₅ haloaUcyl;

R²⁸ is hydrogen, C_x-C₁₀ alkyl, or C_x-C_xo haloaUcyl;

R²⁹ is C_x-C₁₀ alkyl; and

R³⁰ is hydrogen, C_x-C_xo aUcyl, C_x-C_xo haloalkyl, C₃-C 10 cycloaUcyl, C₃-C_X0 halocycloalkyl, or optionaUy substituted phenyl.

3. The uratil compound according to claim 1 or 2, wherein X and Y are both oxygen.

4. The uratil compound according to any one of claims 1 to 3, wherein Z is oxygen.

5. The uratil compound according to any one of claims 1 to 3, wherein Z is sulfur.

6. The uratil compound according to any one of claims 1 to 5, wherein R¹ is hydrogen or C_x-C₃ alkyl.

7. The uratil compound according to any one of claims 1 to 6, wherein R² is C_x-C₃ alkyl.

8. The uratil compound according to any one of claims 1 to 6, wherein R² is methyl.

9. The uratil compound according to any one of claims 1 to 6, wherein R² is amino.

10. The uratil compound according to any one of claims 1 to 9, wherein R³ is C_x-C₃ haloaUcyl.

11. The uratil compound according to any one of claims 1 to 9, wherein R³ is trifluoromethyl.

12. The uracU compound according to any one of claims 2 to 11, wherein R⁷ is chlorine.

13. The uracil compound according to claim 12, wherein R⁸ is 1-(C_X-C₁₀ alkoxy)carbonylethoxy.

14. The uracil compound according to claim 12, wherein R⁸ is

1 -(methoxycarbonyl)ethoxy .

15. The uracil compound according to claim 12, wherein R⁸ is l-(ethoxycarbonyl)ethoxy.

16. The uracU compound according to any one of claims 2 to 11, wherein R⁷ is NO₂.

17. The uracil compound according to claim 16, wherein R⁸ is C_x-C_xo aUcoxy.

18. The uratil compound according to claim 16, wherein R⁸ is methoxy.

19. The uratil compound according to claim 16, wherein R⁸ is isopropoxy.

20. A herbicidal composition which comprises a uratil compound according to any one of claims 1 to 19 and 36, and an inert carrier or dUuent.

21. A method for controlling weeds, which comprises applying a herbicidaUy effective amount of a uratil compound according to any one of claims 1 to 19 to the weeds or to a place where the weeds are growing or wiU grow.

22. Use of a uracil compound according to any one of claims 1 to

19 as a herbicide.

23. A uratil compound of the general formula:

wherein R\ R³, Q, X, Y, and Z are as defined in claim 1.

24. The uratil compound according to claim 23, wherein Q is a group of the general formula:

R° R*

ft R^c wherein R⁴, R⁵, R⁶, R⁷, and R⁸ are as defined in claim 2.

25. The uratil compound according to claim 23 or 24, wherein X and Y are both oxygen.

26. The uratil compound according to any one of claims 23 to 25, wherein Z is oxygen.

27. The uracil compound according to any one of claims 23 to 25, wherein Z is sulfur.

28. The uracil compound according to any one of claims 23 to 27, wherein R³ is trifluoromethyl.

29. A uratil compound of the general formula:

wherein R¹, X, Y, and Z are as defined in claim 1;

R²⁰⁰ is hydrogen, C_x-C₃ alkyl, C_x-C₃ haloaUcyl, C₃-C₆ aUcenyl, C₃-C₆ aUcynyl, or N(R⁶¹)R⁶² wherein R⁶¹ and R⁶² are as defined in claim 1; R³⁰⁰ is C_x-C₃ haloalkyl; or

R²⁰⁰ and R³⁰⁰ may be combined at their ends to form optionaUy fluorine-substituted trimethylene or optionaUy fluorine-substituted tetramethylene.

30. The uratil compound according to claim 29, wherein X and Y are both oxygen.

31. The uratil compound according to claim 29 or 30, wherein Z is oxygen.

32. The uracil compound according to claim 29 or 30, wherein Z is sulfur.

33. The uratil compound according to any one of claims 29 to 32, wherein R³⁰⁰ is trifluoromethyl.

34. The uratil compound according to any one of claims 29 to 33, wherein R²⁰⁰ is methyl.

35. The uratil compound according to any one of claims 29 to 33, wherein R²⁰⁰ is amino.

36. The uratil compound according to claim 16, wherein R⁸ is 2,2-di(C_x-C₅ alkyl)hydrazino.