GB2515002A

GB2515002A - Mixtures of haloalkylsulfonanilide derivatives and safeners

Info

Publication number: GB2515002A
Application number: GB201308608A
Authority: GB
Inventors: William Guy Whittingham
Original assignee: Syngenta Ltd
Current assignee: Syngenta Ltd
Priority date: 2013-05-14
Filing date: 2013-05-14
Publication date: 2014-12-17
Also published as: GB201308608D0

Abstract

The present invention relates to compositions for protecting crops of useful plants from the harmful effects of certain sulphonanilide derivative herbicides as well as methods for protecting crops of useful plants from the harmful effects of these herbicides and methods for combating weeds in crops of useful plants. The sulfonanilide derivative of formula (I) is mixed with a safener selected from from the group consisting of AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, TI-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (CAS RN 221668-34-40 4) and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide.

Description

MIXTURES OF HALOALKYLSULFONANILIDE DERIVATIVES AND SAFENERS

The present invention relates to mixtures of herbicidal haloalkylsulfonanilide derivatives and a safener.

Some haloalkylsulfonanilide derivatives are known to have herbicidal activities -see EP 2 420 493 and EP 2 336 104.

The object of the present invention is to provide a mixtures of a herbicidal haloalkylsulfonanilide derivatives and a safener.

Accordingly, the present invention provides a composition comprising a haloalkylsulfonanilide derivative represented by the formula (1) or an agrochemically acceptable salt thereof: çA wherein Ais-C(R7)(R8)-or-N(R9)-, W is an oxygen atom or a sulfur atom, n is an integer of from ito 4, R1 is halo 01.06 alkyl, R2 is a hydrogen atom, C 0e alkyl, halo C £6 alkyl, 02-C6 alkenyl, halo 02-Ce alkenyl, 02 C alkynyl, halo 02C6 alkynyl, C £6 alkoxy C £ alkyl, halo C -C alkoxy 01-06 alkyl, 01-06 alkoxy C £6 alkoxy C £6 alkyl, tn C £e alkylsilyl Ci 0e alkoxy C £6 alkyl, phenyl C -Ce alkyl, substituted phenyl C £6 alkyl having at least one substituent selected from Y, C -C 2 alkylcarbonyl, halo C -C 2 alkylcarbonyl, cyclo 03-Ce alkylcarbonyl, cyclo 03-Ce alkyl C -06 alkylcarbonyl, 02-06 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y, heterocyclic carbonyl, substituted heterocyclic carbonyl having at least one substituent selected from Y, C -C 2 alkoxycarbonyl, halo C -C 2 alkoxycarbonyl, C £e alkoxy C £e alkoxycarbonyl, C £e alkylthio C £6 alkoxycarbonyl, 01 £6 alkylsulfinyl C £6 alkoxycarbonyl, C £6 alkylsulfonyl 0 alkoxycarbonyl, 02.06 alkenyloxycarbonyl, halo 02.06 alkenyloxycarbonyl, 02.06 alkynyloxycarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl having at least one substituent selected from Y, phenyl C.06 alkoxycarbonyl, substituted phenyl C.06 alkoxycarbonyl having at least one substituent selected from Y, phenoxy C. 0 alkylcarbonyl, substituted phenoxy C.06 alkylcarbonyl having at least one substituent selected from Y, mono(C1 -C alkyaminocarbonyl, mono(halo 01 -06 alkyl)aminocarbonyl, symmetric or asymmetric di(01 -06 alkyl)aminocarbonyl, symmetric or asymmetric halo di(Ci -06 alkyl)aminocarbonyl, C -06 alkylthiocarbonyl, halo 01 -C alkylthiocarbonyl, 01 -06 alkylsulfonyl, halo C -Ce alkylsulfonyl, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y, 0 £ alkylthio C -C alkyl, halo C -alkylthio 0 Ce alkyl, phenyl C -06 alkoxy 01 -06 alkyl, substituted phenyl C -Ce alkoxy Ci -Ce alkyl having at least one substituent selected from Y, phenylthio C alkyl, substituted phenylthio C C alkyl having at least one substituent selected from Y, phenyl Ci £e alkylthio C £6 alkyl, substituted phenyl C alkylthio C £ alkyl having at least one substituent selected from Y, phenylsulfonyl C -C alkyl, substituted phenylsulfonyl C alkyl having at least one substituent selected from Y, phenyl Ci C alkylsulfonyl C 0 alkyl, substituted phenyl C1C6 alkylsulfonyl C £6 alkyl having at least one substituent selected from Y, C alkylcarbonyloxy C £ alkyl, phenylcarbonyloxy C alkyl, substituted phenylcarbonyloxy C C6 alkyl having at least one substituent selected from 1, phenylcarbonyl C Ce alkyl, substituted phenylcarbonyl C alkyl having at least one substituent selected from Y, C C6 alkoxycarbonyloxy C C6 alkyl, phenylcarbonyloxy C -06 alkoxy C C6 alkyl, substituted phenylcarbonyloxy C alkoxy C alkyl having at least one substituent selected from Y, mono C 06 alkylaminocarbonyloxy C 06 alkyl, symmetric or asymmetric di(C1 -alkyl)aminocarbonyloxy C £ alkyl, phenylaminocarbonyloxy C £6 alkyl, substituted phenylaminocarbonyloxy C £6 alkyl having at least one substituent selected from Y, C £6 alkyl(phenyl)aminocarbonyloxy C -0 alkyl, substituted C £6 alkyl(phenyl)aminocarbonyloxy C -alkyl having at least one substituent selected from Y, C £6 alkylcarbonyl C £6 alkyl, C £6 alkoxycarbonyl C £6 alkyl, halo C -0 alkylthio, symmetric or asymmetric di(C1 £6 alkyl)aminothio or cyano, each of R3 and R4 is independently a hydrogen atom, C alkyl, halo C alkyl, cyclo 03 0 alkyl, halocyclo 03-06 alkyl, C1 £6 alkoxy, halo C -C6 alkoxy, halogen or cyano, or R3 and Ft4 may form a 3-to 7-membered ring together with each other, each of R5, R6, R7 and R9 is independently a hydrogen atom, a halogen, C alkyl, halo C alkyl, 020e alkenyl, C2C6 alkynyl, cyclo 03-06 alkyl, halocyclo 03-06 alkyl, C1 -Ce alkoxy Ci Ce alkyl, halo C -0e alkoxy C 0e alkyl, hydroxy C -0e alkyl, alkylthio CC alkyl, halo C -alkylthio C C alkyl, mono(01 06 alkyamino C -C6 alkyl, symmetric or asymmetric di(01 -C6 alkyl)amino C alkyl, phenyl, substituted phenyl having at least one substituent selected from Y, heterocyclyl, substituted heterocyclyl having at least one substituent selected from Y, phenyl C C6 alkyl, substituted phenyl C C6 alkyl having at least one substituent selected from Y, phenoxy C 06 alkyl, substituted phenoxy C alkyl having at least one substituent selected from Y, C alkylcarbonyl, halo C Ce alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y, C C alkoxycarbonyl, halo C C alkoxycarbonyl, carboxyl, mono(C1 £ alkyl)aminocarbonyl, symmetric or asymmetric di(C1 C6 alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from Y on the ring, phenyl C -C alkylaminocarbonyl, substituted phenyl C C6 alkylaminocarbonyl having at least one substituent selected from Y on the ring, C £6 alkoxy, halo C £ alkoxy, phenoxy, substituted phenoxy having at least one substituent selected from Y on the ring, C C6 alkylthio, halo C C6 alkylthio, phenylthio, substituted phenylthio having at least one substituent selected from Y on the ring, 0 0 alkylsulfonyl, halo 0 0 alkylsulfonyl, mono(01 0 alkyl)amino, di(01 -06 alkyl)amino, 01 -06 alkylcarbonyloxy, hydroxy, amino, cyano or nitro, R9 is a hydrogen atom, 01-06 alkyl, halo 01-06 alkyl, cyclo 03-C6 alkyl, halocyclo 03-C6 alkyl, 02-06 alkenyl, halo 02-06 alkenyl, 02-06 alkynyl, 01-06 alkoxy 01-06 alkyl, halo 01-06 alkoxy 0 alkyl, hydroxy alkyl, cyclo 03-Ce alkyl C -C alkyl, phenyl 01-06 alkyl, substituted phenyl 01 C6 alkyl having at least one substituent selected from Y on the ring, phenyl, substituted phenyl having at least one substituent selected from Y on the ring, phenoxy C -06 alkyl, substituted phenoxy C -C6 alkyl having at least one substituent selected from Von the ring, C -C6 alkylcarbonyl C 0 alkyl, halo Cl_Ce alkylcarbonyl 0C alkyl, 01C6 alkoxycarbonyl 01-06 alkyl, halo C0 alkoxycarbonyl C £6 alkyl, C £6 alkylcarbonyl, halo Cl_Ce alkylcarbonyl, cyclo 03-06 alkylcarbonyl, cyclo C3C6 alkyl 0 0 alkylcarbonyl, C2C6 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Von the ring, heterocyclic carbonyl, substituted heterocyclic carbonyl having at least one substituent selected from Y, Cl -06 alkoxycarbonyl, halo C 0e alkoxycarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl having at least one substituent selected from Y, aminocarbonyl, mono(C1 C alkyl)aminocarbonyl, monohalo(Ci -C6 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 06 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1 C alkyaminocarbonyl, C Ce alkylthiocarbonyl, halo C Ce alkylthiocarbonyl, C1 -C6 alkylsulfonyl, halo 01 £6 alkylsulfonyl, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y, C -06 alkylthio Cl -06 alkyl, halo 01 -06 alkylthio C1 -C6 alkyl, phenylthio C1 -C6 alkyl, substituted phenylthio C1 C alkyl having at least one substituent selected from Y, C1 -C6 alkylsulfinyl C1 -C6 alkyl, halo C alkylsulfinyl C1 -C6 alkyl, phenylsulfinyl C1 C alkyl, substituted phenylsulfinyl 01 -06 alkyl having at least one substituent selected from Y, C Ce alkylsulfonyl C1 -C6 alkyl, halo 01 06 alkylsulfonyl C1 06 alkyl, phenylsulfonyl C C alkyl, substituted phenylsulfonyl Ci 0e alkyl having at least one substituent selected from Y, cyano, amino or hydroxy, or R5, R6, R7 or R5 may form, together with R5, R6, R7 or on the same carbon, an optionally substituted 3-to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with Ci -06 alkyl, C2 C6 alkenyl, 02 £ alkynyl or cyclo C3 alkyl), an olefin or carbonyl, or R5, R6, R7 or R8 may form, together with R5, R6, R7 or R6 on a different carbon, an optionally substituted 3-to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with Ci C alkyl, C2 C alkenyl, C206 alkynyl or cyclo 03-C6 alkyl), or R5 or R6 may form a bond together with R5 or R6 on an adjacent carbon, when n is from 2 to 4, R5 or R6 may be the same as or different from R5 or R6 on an adjacent carbon, Xis halogen, CiCe alkyl, 0206 alkenyl, 0206 alkynyl, cyclo CC alkyl, halo CiC alkyl, halocyclo 03-Ce alkyl, C C alkoxy, halo 01 -06 alkoxy, Cl 06 alkylthio, halo 0 0e alkylthio, 0 -C alkylsulfinyl, halo C C alkylsulfinyl, C C alkylsulfonyl, halo Cl 0e alkylsulfonyl, phenyl, substituted phenyl having at least one substituent selected from Y on the ring, heterocyclyl, substituted heterocyclyl having at least one substituent selected from Y on the ring, phenoxy, substituted phenoxy having at least one substituent selected from Y on the ring, phenylthio, substituted phenylthio having at least one substituent selected from Y on the ring, phenylsulfinyl, substituted phenylsulfinyl having at least one substituent selected from Y on the ring, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y on the ring, 01 -06 alkylcarbonyl, halo Ci Ce alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y on the ring, 01 -06 alkoxycarbonyl, halo C1 -C6 alkoxycarbonyl, carboxyl, mono(C1 -Ce alkyl)aminccarbonyl, monohalo(C1 -C6 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -C5 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1 -C alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from Y on the ring, phenyl 01-06 alkylaminocarbonyl, substituted pheny IC1 -C6 alkylaminocarbonyl having at least one substituent selected from Ion the ring, hydroxy, amino, cyanc or nitro, Visa halogen, C1 -C6 alkyl, C2 -06 alkenyl, 02-06 alkynyl, cyclo 03-C6 alkyl, halo 01 0 alkyl, halocyclo C3 alkyl, C1 -C6 alkoxy, halo C1 -C6 alkoxy, C1 -C6 alkylthio, halo C1 -C6 alkylthio, C1 - 0 alkylsulfinyl, halo 0 alkylsulfinyl, 0 alkylsulfonyl, halo C1 -C6 alkylsulfonyl, phenyl, substituted phenyl having at least one substituent selected from the group consisting of halogen, C1 -C6 alkyl, 02-C6 alkenyl, C2 -C alkynyl, cyclo 03-06 alkyl, halo 0 -C6 alkyl, halocyclo C3 -C6 alkyl, C -C6 alkoxy, halo C1 -C6 alkoxy, C1 -C6 alkylthio, halo C1 -C6 alkylthio, C1 -C5 alkylsulfinyl. halo C1 -C5 alkylsulfinyl, C £6 alkylsulfonyl, halo C -C alkylsulfonyl, C -C6 alkylcarbonyl, halo C -C alkylcarbonyl, C1 -C6 alkoxycarbonyl, carboxyl, mono(C1 -C6 alkyaminocarbonyl, symmetric or asymmetric di(C1 alkyaminocarbonyl, hydroxy, amino, cyano and nitro, heterocyclyl, substituted heterocyclyl having at least one substituent selected from the group consisting of halogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, cyclo C3 -C6 alkyl, halo C1 -C6 alkyl, halocyclo C3 -C6 alkyl, C1 -C6 alkoxy, halo C1 -06 alkoxy, C1 -Ce alkylthio, halo C1 alkylthio, 01 -06 alkylsulfinyl, halo C1 alkylsulfinyl, C1 -C8 alkylsulfonyl, halo C1 -C6 alkylsulfonyl, C1 -C5 alkylcarbonyl, halo C1 alkylcarbonyl, C1 -C6 alkoxycarbonyl, carboxyl, mono(C1 -C6 alkyaminocarbonyl, symmetric or asymmetric di(C1 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenoxy, substituted phenoxy having at least one substituent selected from the group consisting of halogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 C alkynyl, cyclo C3 C alkyl, halo C -0 alkyl, halocyclo 0 0 alkyl, 0 £5 alkoxy, halo C1 -C6 alkoxy, C1 -C6 alkylthio, halo C1 -C6 alkylthio, C1 -C6 alkylsulfinyl, halo C1 -C5 alkylsulfinyl, C £ alkylsulfonyl, halo C1 -C6 alkylsulfonyl, C1 -C6 alkylcarbonyl, halo C -C6 alkylcarbonyl, C -C alkoxycarbonyl, carboxyl, mono(Ci -C alkyaminocarbonyl, symmetric or asymmetric di(C1 -C6 alkyaminocarbonyl, hydroxyl, amino, cyano and nitro, phenylthio, substituted phenylthio having at least one substituent selected from the group consisting of halogen, C1 -C6 alkyl, C2 -C alkenyl, C2 -C6 alkynyl, cyclo C3 -C6 alkyl, halo C1 -C6 alkyl, halocyclo C3 -C alkyl, C1 -C6 alkoxy, halo C1 £6 alkoxy, C1 -C alkylthio, halo C1 -C3 alkylthio, C £6 alkylsulfinyl, halo C1 -C3 alkylsulfinyl, C1 -C6 alkylsulfonyl, halo C1 -C6 alkylsulfonyl, C1 -C6 alkylcarbonyl, halo C1 -alkylcarbonyl, C1 -C6 alkoxycarbonyl, carboxyl, mono(C1 -C6 alkyaminocarbonyl, symmetric or asymmetric di(Ci -C3 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfinyl, substituted phenylsulfinyl having at least one substituent selected from the group consisting of halogen, 01 £6 alkyl, 02-06 alkenyl, 02-06 alkynyl, cyclo 03-06 alkyl, halo 01-06 alkyl, halocyclo 03-0 alkyl, 0C alkoxy, halo 01-06 alkoxy, 0-0 alkylthio, halo 01-06 alkylthio, 01-06 alkylsulfinyl, halo 01-06 alkylsulfinyl, C -06 alkylsulfonyl, halo 01 -06 alkylsulfonyl, 01 -06 alkylcarbonyl, halo C -C alkylcarbonyl, Ci 0e alkoxycarbonyl, carboxyl, mono(C1 £ alkyaminocarbonyl, symmetric or asymmetric di(01 alkyaminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from the group consisting of halogen, Ci Ce alkyl, C2 £ alkenyl, 02 £6 alkynyl, cyclo C3 -C6 alkyl, halo C1 £ alkyl, halocyclo 03 Ce alkyl, C -Ce alkoxy, halo C -C alkoxy, C -06 alkylthio, halo C Le alkylthio, C -06 alkylsulfinyl, halo Ci -06 alkylsulfinyl, C alkylsulfonyl, halo C C alkylsulfonyl, C 05 alkylcarbonyl, halo C £6 alkylcarbonyl, C1 -C6 alkoxycarbonyl, carboxyl, mono(C1 £ alkyl)aminocarbonyl, symmetric or asymmetric di(01 -06 alkyaminocarbonyl, hydroxy, amino, cyano and nitro, C -06 alkylcarbonyl, halo C1 -C6 alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from the group consisting of halogen, C Le alkyl, 02-06 alkenyl, 02-06 alkynyl, cycloo3 -06 alkyl, halo C £ alkyl, halocyclo C £6 alkyl, C alkoxy, halo C1 -C6 alkoxy, C £6 alkylthio, halo C1 -06 alkylthio, 01-06 alkylsulfinyl, halo C -06 alkylsulfinyl, C C alkylsulfonyl, halo 01-06 alkylsulfonyl, C1 £ alkylcarbonyl, halo C1 £ alkylcarbonyl, C -C6 alkoxycarbonyl, carboxyl, mono(01 -06 alkyl)aminocarbonyl, symmetric or asymmetric di(01 -06 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, 0 £ alkoxycarbonyl, carboxyl, mono(C1 £6 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -06 alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from the group consisting of halogen, 01 -06 alkyl, 02-06 alkenyl, 02-0 alkynyl, cyclo 03-06 alkyl, halo C -06 alkyl, halocyclo 03-06 alkyl, C -06 alkoxy, halo C C alkoxy, C -06 alkylthio, halo C -06 alkylthio, C -06 alkylsulfinyl, halo C C alkylsulfinyl, C -C6 alkylsulfonyl, halo C £6 alkylsulfonyl, C -C6 alkylcarbonyl, halo 01 £6 alkylcarbonyl, 01 £6 alkoxycarbonyl, carboxyl, mono(01 -06 alkyl)aminocarbonyl, symmetric or asymmetric di(01 -06 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenyl C -06 alkylaminocarbonyl, substituted phenyl C -06 alkylaminocarbonyl having at least one substituent selected from the group consisting of halogen, C £ alkyl, 02-06 alkenyl, 02-06 alkynyl, cyclo 03-06 alkyl, halo C £ alkyl, halocyclo 03-06 alkyl, 01-06 alkoxy, halo C -06 alkoxy, 01-06 alkylthio, halo 01-06 alkylthio, 01-06 alkylsulfinyl, halo C Le alkylsulfinyl, C -06 alkylsulfonyl, halo C -0 alkylsulfonyl, C -Ce alkylcarbonyl, halo C -06 alkylcarbonyl, C -06 alkoxycarbonyl, carboxyl, mono(C1 £ alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, hydroxy, amino, cyano or nitro, or Y may be C £4 alkylene, halo C £4 alkylene, 02 04 alkenylene or halo 02 04 alkenylene which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with 0 0 alkyl, 02 06 alkenyl, C2 C6 alkynyl or cyclo 03-06 alkyl) and form a 5-or 6-membered ring together with an adjacent carbon or nitrogen atom on a benzene ring or a heterocyclyl, and the heterocyclyl is thienyl, furyl. pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothienyl, benzofuryl, indolyl, benzothiazolyl, benzoimidazolyl, benzoisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl, provided that in a group having two or more substituents, the substituents may be the same or different, and a safener selected from AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, Tl-35, N-isopropyl-4- (2-methoxy-benzoylsulfamoyl)-benzamide (CAS RN 221668-34-4) and N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide.

When the compounds of the present invention have at least one asymmetric carbon atom, the present invention covers all the optical isomers, racemates and diastereomers thereof.

Now, the options for A, W, R1, R2, R3, R.4, R5, R6, R7, R8, R9, n and X will be illustrated.

As options for A, the following are, for example, mentioned: Al: -0(R4(R8)-, and All: -N(R9)-.

As options for W, the following are, for example, mentioned: WI: an oxygen atom, and WIl: a sulfur atom.

As options for R1, the following are, for example, mentioned.

R11: trifluoromethyl, and R111: halo 01.06 alkyl.

As options for R2, the following are, for example, mentioned.

R21: a hydrogen atom, 01-012 alkylcarbonyl, halo 01.012 alkylcarbonyl, 02.06 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y, C.01 2 alkoxycarbonyl, halo C.01 2 alkoxycarbonyl, 02.06 alkenyloxycarbonyl, phenoxycarbonyl, Ci 0e alkylthiocarbonyl or halo C -C alkylthiocarbonyl, R211: 01.06 alkyl, 01.06 alkoxy alkyl, phenyl 01.06 alkyl, substituted phenyl 0. 0 alkyl having at least one substituent selected from Y on the ring, C.C alkylthio C.06 alkyl, halo 01.C alkylthio C.06 alkyl, phenoxy C.06 alkyl or C.0 alkylcarbonyloxy C.06 alkyl, and R2111: 01.06 alkylsulfonyl, halo 01.06 alkylsulfonyl, phenylsulfonyl or substituted phenylsulfonyl having at least one substituent selected from Y. As options for R3, the following are, for example, mentioned: R31: a hydrogen atom, and R311: Cl_Ce alkyl, halo CC alkyl, C3C6 cycloalkyl, halo 03-Ce cycloalkyl, C1C6 alkoxy, halo C1 -C alkoxy, halogen or cyano.

As options for R4, the following are, for example, mentioned: R41: a hydrogen atom, and R411: Ci -06 alkyl, halo 01C6 alkyl, 03-06 cycloalkyl, halo 03-06 cycloalkyl, 01-06 alkoxy, halo C -C alkoxy, halogen or cyano.

As options for R5, R6, R7 and R8, the following are, for example, mentioned: R51, R61, R71 or R61: a hydrogen atom, CC alkyl, 02-06 alkenyl, 02-Ce alkynyl, cyclo 03-06 alkyl, halo 01 -C alkyl, halocyclo 03 06 alkyl, CC alkoxy 06 alkyl, halo Cl_Ce alkoxy CCe alkyl, C alkylthio C1C6 alkyl or halo C alkylthio C1 alkyl, R511, R611, R711 or R511: phenyl or substituted phenyl having at least one substituent selected from Y on the ring, R5111, R6111, R7111 or R3111: halogen, C1 -C6 alkoxy, 01-06 alkylthio, hydroxy, amino, cyano or nitro, and R5IV, R5IV, R7IV or R6IV: C -C6 alkylcarbonyl, halo C1 £ alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y on the ring or C1 06 alkoxycarbonyl.

As options for R9, the following are, for example, mentioned: R91: a hydrogen atom, C1C6 alkyl, halo C C alkyl, cyclo C C6 alkyl, halocyclo 03-06 alkyl, 01- 06 alkoxy ci £ alkyl, halo C.C alkoxy Ci.C alkyl, phenyl ci £ alkyl, substituted phenyl Ci.C alkyl having at least one substituent selected from Y on the ring, phenyl or substituted phenyl having at least one substituent selected from Y on the ring, and R91 I: C1 Ce alkylcarbonyl, halo C -C6 alkylcarbonyl, cyclo 03.05 alkylcarbonyl, cyclo 03. C6 alkyl 06 alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y, C £ alkoxycarbonyl, halo C1 alkoxycarbonyl, phenoxycarbonyl or substituted phenoxycarbonyl having at least one substituent selected from Y, and R9111: C1 £ alkylsulfonyl, halo 0 0e alkylsulfonyl, phenylsulfonyl or substituted phenylsulfonyl having at least one substituent selected from Y. As options for n, the following are, for example, mentioned: nI: 3 or4, and nIl: 1 or2.

As options for X, the following are, for example, mentioned: Xl: a hydrogen atom, XII: a halogen, C1 -0 alkoxy, halo C1 -C alkoxy, C1 -C alkylthio, halo C1 -C alkylthio, phenoxy, substituted phenoxy having at least one identical or different substituent selected from Y on the ring, phenylthio, substituted phenylthio having at least one identical or different substituent selected from 1, hydroxy, amino, cyano or nitro, XIII: C1 -0 alkyl, cyclo 03-0 alkyl, halo C1 -C alkyl, halocyclo 03 0 alkyl, C1 -C alkoxy C -0 alkyl or halo C -C alkoxy C1 -C alkyl, XIV: C -C alkylcarbonyl, halo C £ alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one identical or different substituent selected from Von the ring or C £6 alkoxycarbonyl, and XV: phenyl, substituted phenyl having at least one identical or different substituent selected from V on the ring, heterocyclyl or substituted heterocyclyl having at least one identical or different substituent selected from Von the ring.

These options for the respective groups may be combined arbitrarily to define the scope of the compounds of the present invention. Examples of combinations of these options for the respective groups are shown in Table 1. However, the combinations shown in Table 1 are mere examples, and the present invention is by no means restricted thereto.

TABLE 1

R R:1 I., R4 R4 1\ R(3 R6l R flIQgl

W A X

WI Al R11 R01 R51 R7i XI nI WI Al l<1 R01 k3I R71 Xli ni WI Al R1 I R0 I R, I R7 I -XIII nI \.VI Al RI 1Z21 RI R71 XIV nI WI Al R11 R0i R31 R-i XV ni WI Al P1 1 P1 1 P3 1 H7 I -Xi nil WI Al R1 I R0 I R, 1 R7 if -XI nI \VI Al N I N 2 N I FE III XI ii WI Al N1! R.,f N31 R7fV Xl ni WI Al P1 i P0 I R II H7 I Xl nI WI Al l<1 N01 k31111-<71 Xl ni WI Al R1 I R0 I R3 IV R7 I -XI nI WI Al P1 I R2 II P3 I H7 I XI nI WI Al R1l R0ii1R31 R7i XI ni WT Al P1 11 P0 1 P3 1 H7 I Xl iii WI All N1 I N01 I(I -R01 Xi nI \\/[ All R1 I H2 I H3 1 -N0, I Xi till WI All P1 I H2 I H3 I H0 II XI nI WI All P1 I P., I P3 I Rq ill XI ni \VI,k[l k11 N0II k3I N91 XI nI \.\t'[ All R11 k.,ll1R,1 -kI Xl nl WI A H N II N., I N I H I XI n I Wil Al N1 I N0 I N3 I FE7 I XI nI \Vli,kll N1! N,l N5I N0 1 XI nI Now, examples of each atom or group in the definitions of R1, R2, R3, R4, R5, R6, R7, R9, R9, R10, R11, X and V will be given.

In one embodiment, n is 1 or 4.

In one embodiment, n is 2 or 3 and each of R5 and R6 is as defined above, with the proviso that at least one of R5 and R6 is not H, C15a1ky1, Oihaloalkyl, C36cycloalkyl, Ci4alkoxyCi4alkyl, phenyl or In one embodiment, W is S. In one embodiment, Xis 02.06 alkyl, 02.06 alkenyl, 02.06 alkynyl, cyclo 03.06 alkyl, halo C1 -C6 alkyl, halocyclo C3 -C6 alkyl, C.C alkoxy, halo C1.C alkoxy, C1 £ alkylthio, halo C.06 alkylthio, C -06 alkylsulfinyl, halo ClCe alkylsulfinyl, C £6 alkylsulfonyl, halo C1 C alkylsulfonyl, phenyl, substituted phenyl having at least one substituent selected from Y on the ring, heterocyclyl, substituted heterocyclyl having at least one substituent selected from Y on the ring, phenoxy, substituted phenoxy having at least one substituent selected from Y on the ring, phenylthio, substituted phenylthio having at least one substituent selected from Y on the ring, phenylsulfinyl, substituted phenylsulfinyl having at least one substituent selected from Y on the ring, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y on the ring, C alkylcarbonyl, halo C alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y on the ring, C £ alkoxycarbonyl, halo C C alkoxycarbonyl, carboxyl, mono(C1 £ alkyl)aminocarbonyl, monohalo(01 £ alkyaminocarbonyl, symmetric or asymmetric di(C1 0e alkyl)aminocarbonyl, symmetric or asymmetric halo di(01 £ alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from Y on the ring, phenyl C -C alkylaminocarbonyl, substituted pheny 101 -06 alkylaminocarbonyl having at least one substituent selected from Y on the ring, hydroxy, amino, cyano or nitro, In one embodiment, R1 is not trifluoromethyl.

R2 is 05-Ce alkyl, halo Cl-Ce alkyl, halo 0206 alkenyl, 04-Ce alkynyl, halo C2Ce alkynyl, 0-C alkoxy Cl-Ce alkyl, 01-C4alkoxyC3-C6alkyl, halo ClC6 alkoxy 01-06 alkyl, 01-05 alkoxy Cl-Ce alkoxy 01- 06 alkyl, tn C1Ce alkylsilyl C-C alkoxy 01-06 alkyl, 06-012 alkylcarbonyl, halo 05-012 alkylcarbonyl, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, halo 05-012 alkoxycarbonyl, C1-C6 alkylthio Cl-Co alkoxycarbonyl, C1-C6 alkylsulfinyl C1-C6 alkoxycarbonyl, C-C alkylsulfonyl C1-C6 alkoxycarbonyl, halo C2-C6 alkenyloxycarbonyl, phenoxy Cl-Ce alkylcarbonyl, phenoxy Cl-Ce alkylcarbonyl substituted with at least one Y, mono(halo C1-C6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1-Ce alkyl)aminocarbonyl, halo Cl-Ce alkylthiocarbonyl, Cs-Ce alkylsulfonyl, halo C5 C alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, halo C-C alkylthio C-C alkyl, phenyl Cl-Ce alkylthio Cl-Ce alkyl, phenyl Cl-Ce alkylthio C1-06 alkyl substituted with at least one Y, phenylsulfonyl Ci-Ce alkyl, phenylsulfonyl Ci-Ce alkyl substituted with at least one Y, phenyl Cl-Ce alkylsulfonyl C1-C6 alkyl, phenyl C1-C6 alkylsulfonyl C-C alkyl substituted with at least one 1, Cl-Ce alkylcarbonyloxy Cl-Ce alkyl, phenylcarbonyloxy Cl-Ce alkyl, phenylcarbonyloxy C1-Ce alkyl substituted with at least one Y, phenylcarbonyl C-C alkyl, phenylcarbonyl 01-C6 alkyl substituted with at least one Y, C1-Ce alkoxycarbonyloxy Cl-Ce alkyl, phenylcarbonyloxy Cl-Ce alkoxy C1-Ce alkyl, phenylcarbonyloxy Cl-Ce alkoxy C1-Ce alkyl substituted with at least one Y, mono C'-Ce alkylaminocarbonyloxy C1-Ce alkyl, symmetric or asymmetric di(C1-Ce alkyl)aminocarbonyloxy C1-06 alkyl, phenylaminocarbonyloxy C1-Ce alkyl, phenylaminocarbonyloxy C-C alkyl substituted with at least one Y, Cl-Ce alkyl(phenyl)aminocarbonyloxy Cl-Ce alkyl, Cl-Ce alkyl(phenyl)aminocarbonyloxy C1-Ce alkyl substituted with at least one Y, C1-C6 alkylcarbonyl C1-C6 alkyl, Cl-Ce alkoxycarbonyl ClC6 alkyl, halo C1-C6 alkylthio, symmetric or asymmetric di(01-C6 alkyl)aminothio or cyano.

In one embodiment, each of R3 and R4 is, independently, a hydrogen atom, 01.06 alkyl, halo C -C alkyl, cyclo 03-0 alkyl, halocyclo 03-C6 alkyl, C1 -C6 alkoxy, halo C1 -C alkoxy, halogen or cyano, or R3 and R.4 may form a 3-to 7-membered ring together with each other, with the proviso that at least one of R3 and R4 is other than a hydrogen atom.

In one embodiment, A is -C(R7)(R6)-and R7 and R3 are, independently, as defined above with the proviso that at least one of R7 and R8 is not H, halogen, 01.4alkyl, 0i.4alkoxy, 0i.4alkylthio or C. 4alkoxycarbonyl.

In one embodiment, A is -N(R9)-and R9 is 05.06 alkyl, halo C.06 alkyl, cyclo 03.06 alkyl, halocyclo 03.06 alkyl, 02.06 alkenyl, halo 02.06 alkenyl, 02.06 alkynyl, 01.06 alkoxy C.06 alkyl, halo C -06 alkoxy C -06 alkyl, hydroxy 0i -06 alkyl, cyclo 03-06 alkyl 0i -06 alkyl, phenyl 01-06 alkyl, substituted phenyl C.06 alkyl having at least one substituent selected from Y on the ring, phenoxy C -0 alkyl, substituted phenoxy C -06 alkyl having at least one substituent selected from Y on the ring, Cl_Ce alkylcarbonyl Cl_Ce alkyl, halo C C6alkylcarbonyl Cl_Ce alkyl, Cl_Ce alkoxycarbonyl C1 -C6 alkyl, halo C1 -0 alkoxycarbonyl C1 -C6 alkyl, 05-C alkylcarbonyl, halo Cl £6 alkylcarbonyl, cyclo 03-Ce alkylcarbonyl, cyclo 03-C6 alkyl Cl -C6 alkylcarbonyl, 0206 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y on the ring, heterocyclic carbonyl, substituted heterocyclic carbonyl having at least one substituent selected from Y, 05-06 alkoxycarbonyl, halo Cl C alkoxycarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl having at least one substituent selected from Y, aminocarbonyl, mono(C1 -C alkyl)aminocarbonyl, monohalo(C1 -C alkyaminocarbonyl, symmetric or asymmetric di(01 C alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1 -06 alkyl)aminocarbonyl, Cl -06 alkylthiocarbonyl, halo C1 -C alkylthiocarbonyl, Cl -C alkylsulfonyl, halo C1 -C alkylsulfonyl, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y, C1 -0 alkylthio C -06 alkyl, halo Cl -06 alkylthio C 0 alkyl, phenylthio Cl -06 alkyl, substituted phenylthio C. C alkyl having at least one substituent selected from Y, Cl.06 alkylsulfinyl C.06 alkyl, halo C1.

C alkylsulfinyl C -06 alkyl, phenylsulfinyl C C alkyl, substituted phenylsulfinyl C 0 alkyl having at least one substituent selected from Y, C.06 alkylsulfonyl C.06 alkyl, halo C.06 alkylsulfonyl C.06 alkyl, phenylsulfonyl C 0 alkyl, substituted phenylsulfonyl C C alkyl having at least one substituent selected from Y, cyano, amino or hydroxyl.

The following symbols herein have the following meanings.

i. iso, 5: secondary, t: tertiary, c: cyclo, p: para.

Heterocyclyl means the following: namely, thienyl such as thiophen-2-yl or thiophen-3-yl, furyl such as furan-2-yl orfuran-3-yl, pyrrolyl such as pyrrol-1-yl, pyrrol-2-yl or pyrrol-3-yl, oxazolyl such as oxazol-2-yl, oxazol-4-yl or oxazol-5-yl, isoxazoly such as isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl, isoxazolinyl such as isoxazolin-3-yl, isoxazolin-4-yl or isoxazolin-5-yl, thiazolyl such as thiazol-2-yl, thiazol-4-yl or thiazol-5-yl, isothiazoly such as isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl, pyrazoly such as pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl, imidazolyl such as imidazol-1-yl, imidazol- 2-yl or imidazol-4-yl, 1,3,4-oxadiazolyl such as 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazoly such as 1,2,4-oxadiazol-3-yI or 1,2,4-oxadiazol-5-yI, 1,3,4-thiadiazolyl such as 1,3,4-thiadiazol-2-yI, 1,2,4-thiadiazolyl such as 1,2,4-thiadiazol-3-ylor 1,2,4-thiadiazol-5-yI, 1,2,4-triazolyl such asl,2,4-triazol-1-yI, 1,2,4-triazol- 3-yl or 124-triazol-5-yI, 1,2,3-thiadiazolyl such as 1,2,3-thiadiazol-4-yI or 1,2,3-thiadiazol-5-yI, 123-triazolyl such as 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl or 1,2,3-triazol-4-yl, 1,2,3,4-tetrazolyl such as 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl or 1,2,3,4-tetrazol-5-yl, pyridyl such as pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, pyrimidinyl such as pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl, pyrazinyl such as pyrazin-2-yl, pyridazinyl such as pyridazin-3-yl or pyridazin-4-yl, 1,3,5-triazinyl such asl,3,5-triazin-2-yl, 1,2,4-triazinyl such as 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl, such as benzothienyl such as benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-4-yl, benzothiophen-5-yl, benzothiophen-6-yl or benzothiophen-7-yl, benzofuryl such as benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl or benzofuran-7-yl, indolyl such as indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl or indol-7-yl, benzothiazolyl such as benzothiazol-2-yl, benzothiazol-4-yl, benzothiazol-5-yl, benzothiazol-6-yl or benzothiazol-7-yl, benzimidazolyl such as benzimidazol-l-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl or benzimidazol-7-yl, benzoisoxazolyl such as benzisoxazol-3-yl, benzisoxazol-4-yl, benzisoxazol-5-yl, benzisoxazol-6-yl or benzisoxazol-7-yl, benzisothiazolyl such as benzisothiazol-3-yl, benzisothiazol-4-yl, benzisothiazol-5-yl, benzisothiazol-6-yl or benzisothiazol-7-yl, indazolyl such as indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl or indazol-7-yl, benzoxazolyl such as benzoxazol-2-yl, benzoxazol-4-yl, benzoxazol-5-yl, benzoxazol-6-yI or benzoxazol-7-yl, q u inolyl such as quinolin-2-yl, quinolin-3-yI, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl or quinolin-8-yl, isoquinolyl such as isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl, quinoxalinyl such as quinoxalin-2-yl, quinoxalin-3-yl, quinoxalin-5-yl, quinoxalin-6-yl, quinoxalin-7-yl or quinoxalin-8-yl, phthalazinyl such as phthalazin-1-yl, phthalazin-4-yl, phthalazin-5-yl, phthalazin-6-yl, phthalazin-7-yl or phthalazin-8-yl, cinnolinyl such as cinnolin-3-yl, cinnolin-4-yl, cinnolin-5-yl, cinnolin-6-yl, cinnolin-7-yl or cinnolin-8-yl, and quinazolinyl such as quinazolin-2-yl, quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl or quinazolin-8-yI. In the present invention, heterocyclylcarbonyl" means the above-mentioned groups attached to carbonyl.

As a halogen, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom may be mentioned.

Alkyl may be methyl, ethyl, propyl, i-propyl, butyl, i-butyl, t-butyl, s-butyl, pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neo-pentyl, hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1- dimethylbutyl, 1,2-dimethylbutyl, I,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1 -ethyl-1-methylpropyl, 1 -ethyl-2-methylpropyl or the like and is selected within a given range of carbon atoms.

Haloalkyl may be fluoromethyl, chloromethyl, bromomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-fluoropropyl, 3-chloropropyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, 4-chlorobutyl, 4-fluorobutyl or the like and is selected within a given range of carbon atoms.

Cycloalkyl may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or the like and is selected within a given range of carbon atoms.

Halocycloalkyl may be 2-fluorocyclopropyl, 1-chiorocyclopropyl, 2-bromo-1-methylcyclopropyl, 2,2-difluorocyclopropyl, 1,2-dichlorocyclopropyl or the like and is selected within a given range of carbon atoms.

Cycloalkylalkyl may be cyclopropylmethyl, 2-cyclopropylethyl, cyclopentylmethyl, cyclohexylmethyl or the like and is selected within a given range of carbon atoms.

Alkenyl may be ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, I,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-hexenyl, 1,1-dimethyl-2-butenyl, 1,2-dimethyl-2-butenyl, 1,3-dimethyl-2- butenyl, 2,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 2-ethyl-2-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl- 1-methyl-2-propenyl or the like and is selected within a given range of carbon atoms.

Haloalkenyl may be 1-chloroethenyl, 2-chloroethenyl, 2-fluoroethenyl, 2,2-dichloroethenyl, 3-chloro-2-propenyl, 3-fluoro-2-propenyl, 2-chloro-2-propenyl, 4-chloro-3-butenyl or the like and is selected within a given range of carbon atoms.

Alkynyl may be ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-methyl-3-pentynyl, 2-methyl- 3-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 2-ethyl-3-butynyl or the like and is selected within a given range of carbon atoms.

Haloalkynyl may be chloroethynyl, fluoroethynyl, bromoethynyl, 3-chloro-2-propynyl, 4-chloro-2-butynyl or the like and is selected within a given range of carbon atoms.

Phenyl having at least one substituent selected from Y may be 2-fluorophenyl, 3-fluorophenyl, 4- fluorophenyl, 2-chlorophenyl, 3-bromophenyl, 4-iodophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,3,4,5,6-pentafluorophenyl, 2-methylphenyl, 2,5-dimethylphenyl, 4-ethenylphenyl, 2-ethynylphenyl, 3-cyclopropylphenyl, 2-cyclopentylphenyl, 4-cyclohexylphenyl, 2-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 4-methoxymethylphenyl, 2-aminophenyl, 4-dimethylaminophenyl, 2- aminocarbonylphenyl, 2-dimethylaminocarbonylphenyl, 4-trifluoromethoxyphenyl, 2- difluoromethoxyphenyl, 2-ethenyloxyphenyl, 3-cyclopropyloxyphenyl, 2-biphenyl, 4-acetylphenyl, 3- methoxycarbonylphenyl, 2-methylthiophenyl, 3-trifluoromethylthiophenyl, 4-difluoromethylthiophenyl, 2- methylsulfinylphenyl, 3-trifluoromethylsulfinylphenyl, 4-clifluoromethylsulfinylphenyl, 2- methylsulfonylphenyl, 3-trifluoromethylsulfonylphenyl, 4-difluoromethylsulfonylphenyl, 2-cyanophenyl, 3- nitrophenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl or the like.

Alkoxy may be methoxy, ethoxy, propyloxy, i-propyloxy, butyloxy, i-butyloxy, s-butyloxy, t-butyloxy, pentyloxy, 1 -methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1 -dimethylpropyloxy, 1,2- dimethylpropyloxy, 2,2-dimethylpropyloxy, 1 -ethylpropyloxy, hexyloxy, 1 -methylpentyloxy, 2- methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1 -dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3- dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2- ethylbutyloxy, 1,1,2-trimethylpropyloxy, I,2,2-trimethylpropyloxy, 1-ethyl-I -methylpropyloxy, 1 -ethyl-2-methylpropyloxy or the like and is selected within a given range of carbon atoms.

Haloalkoxy may be fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoroniethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, 1 -fluoropropyloxy, 2-fluoropropyloxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 1-fluorobutyloxy, 2-fluorobutyloxy, 3-fluorobutyloxy, 4-fluorobutyloxy, 4-chlorobutyloxy or the like and is selected within a given range of carbon atoms.

Phenylalkyl and phenylalkyl having at least one substituent selected from Y on the ring may be benzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-iodobenzyl, 2,4- diflucrobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-methoxybenzyl, 4-amincbenzyl, 4- trifluoromethoxybenzyl, 2-methylthiobenzyl, 3-trifluoromethylthiobenzyl, 2-cyanobenzyl 4-nitrobenzyl, 2-trifluoromethylbenzyl, 2-phenethyl or the like and is selected within a given range of carbon atoms.

Phenylcarbonylalkyl and phenylcarbonylalkyl having at least one substituent selected from Y on the ring may be phenylcarbonylmethyl, 2-fluorophenylcarbonylmethyl, 2-chlorophenylcarbonylmethyl, 3- bromophenylcarbonylmethyl, 4-iodophenylcarbonylmethyl, 4-methylphenylcarbonylmethyl, 2-methoxyphenylcarbonylmethyl, 4-aminophenylcarbonylmethyl, 4-trifl uoromethoxyphenylcarbonylmethyl 2-methylthiophenylcarbonylmethyl, 3-trifluoromethylthiophenylcarbonylmethyl, 2- cyanophenylcarbonylmethyl, 4-nitrophenylcarbonylmethyl, 2-trifluoromethylphenylcarbonylmethyl, 2-phenylcarbonylethyl or the like and is selected within a given range of carbon atoms.

Phenoxy having at least one substituent selected from Y on the ring may be 2-fluorophenoxy, 2- chlorophenoxy, 4-bromophenoxy, 4-methylphenoxy, 2-methoxyphenoxy, 3-aminophenoxy, 4- trifluoromethoxyphenoxy, 2-methylthiophenoxy, 3-trifluoromethylthiophenoxy, 4-cyanophenoxy, 2-nitrophenoxy, 4-trifluoromethylphenoxy or the like.

Alkylthio may be methylthio, ethylthio, propylthio, i-propylthio, butylthio, i-butylthio, s-butylthio, t-butylthio or the like and is selected within a given range of carbon atoms.

Haloalkylthio may be fluoromethylthio, chloromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-fluoroethylthio, pentafluoroethylthio or the like and is selected within a given range of carbon atoms.

Phenylthio having at least one substituent selected from Y on the ring may be 2-fluorophenylthic, 2-chlorophenylthio, 4-brcmophenylthio, 4-methylphenylthic, 2-methoxyphenylthio, 3-aminophenylthic, 4-trifluoromethoxyphenylthio, 2-methylthiophenylthio, 3-trifluoromethylthiophenylthio, 4-cyanophenylthio, 2-nitrophenylthio, 4-trifluoromethylphenylthio or the like.

Alkylsulfinyl may be methylsulfinyl, ethylsulfinyl, propylsulfinyl, i-propylsulfinyl, butylsulfinyl, butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl or the like and is selected within a given range of carbon atoms.

Haloalkylsulfinyl may be fluoromethylsulfinyl, chioromethylsulfinyl, chiorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoroniethylsulfinyl, trichioromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsu Ifinyl, 2-fluoroethylsulfinyl, pentafluoroethylsulfi nyl or the like and is selected within a given range of carbon atoms.

Phenylsulfinyl having at least one substituent selected from Y on the ring may be 2- fluorophenylsulfinyl, 2-chlorophenylsulfinyl, 4-bromophenylsulfinyl, 4-methylphenylsulfinyl, 2- methoxyphenylsulfinyl, 3-aminophenylsulfinyl, 4-trifluoromethoxyphenylsulfinyl, 2-methyithiophenylsulfinyl, 3-trifluoromethylthiophenylsulfinyl, 4-cyanophenylsulfinyl, 2-nitrophenylsulfinyl, 4-trifluorornethylphenylsulfinyl or the like.

Alkylsulfonyl maybe methylsulfonyl, ethylsulfonyl, propylsulfonyl, i-propylsulfonyl, butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl or the like and is selected within a given range of carbon atoms.

Haloalkylsulfonyl may be fluoromethylsulfonyl, chioromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-fluoroethylsulfonyl, pentafluoroethylsulfonyl orthe like and is selected within a given range of carbon atoms.

Phenylsulfonyl having at least one substituent selected from Y on the ring may be 2- fluorophenylsulfonyl, 2-chiorophenylsulfonyl, 4-bromophenylsulfonyl, 4-methylphenylsulfonyl, 2- methoxyphenylsulfonyl, 3-aminophenylsulfonyl, 4-trifluoromethoxyphenylsulfonyl, 2- methylthiophenylsulfonyl, 3-trifluoromethylthiophenylsulfonyl, 4-cyanophenylsulfonyl, 2-nitrophenylsulfonyl, 4-trifluoromethylphenylsulfonyl or the like.

Alkylcarbonyl may be acetyl, propionyl, butyryl, i-butyryl, valeroyl, i-valeroyl, 2-methylbutyryl, piva loyl, hexanoyl, 2-ethylbutyryl, 2-methylvaleroyl, 4-methylvaleroyl heptanoyl 2,2-dimethylvaleroyl, 2-ethylhexanoyl, 2-propylvaleroyl, octanoyl, nonanoyl, 3,5,5-trimethylhexanoyl, decanoyl or the like and is selected within a given range of carbon atoms.

Haloalkylcarbonyl may be fluoroacetyl, chloroacetyl difluoroacetyl, dichloroacetyl trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, 4-chlorobutyryl heptafluorobutyryl, 3-chloro-2,2-dimethylpropionyl or the like and is selected within a given range of carbon atoms.

Cycloalkylcarbony may be cyclopropanecarnonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl or the like and is selected within a given range of carbon atoms.

Cycloalkylalkylcarbonyl may be cyclopropylmethylcarbonyl, 2-cyclopropylethylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylmethylcarbonyl or the like and is selected within a given range of carbon atoms.

Alkenylcarbonyl may be ethenylcarbonyl, 1-propenylcarbonyl, 2-propenylcarbonyl, 1-butenylcarbonyl, 1-methyl-2-propenylcarbonyl, 2-methyl-2-propenylcarbonyl, 1-hexenylcarbonyl or the like and is selected within a given range of carbon atoms.

Phenylcarbonyl having at least one substituent selected from Y on the ring may be 2- fluorophenylcarbonyl, 2-chiorophenylcarbonyl, 4-bromophenylcarbonyl, 4-methylphenylcarbonyl, 2- methoxyphenylcarbonyl, 3-aminophenylcarbonyl, 4-trifluoromethoxyphenylcarbonyl, 2- methyithiophenylcarbonyl, 3-trifluoroniethylthiophenylcarbonyl, 4-cyanophenylcarbonyl, 2-nitrophenylcarbonyl, 4-trifluoromethyiphenylcarbonyl.

Alkoxycarbonyl may be methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, i-propyloxycarbonyl, butyloxycarbonyl, s-butyloxycarbonyl, i-butyloxycarbonyl, t-butyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl or the like and is selected within a given range of carbon atoms.

Haloalkoxycarbonyl may be fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, 1 -fluoroethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2- bromoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 1- fluoropropyloxycarbonyl, 2-fluoropropyloxycarbonyl, 3-fluoropropyloxycarbonyl, 3-chloropropyloxycarbonyl, 3-bromopropyloxycarbonyl, 4-fluorobutyloxycarbonyl, 4-chlorobutyloxycarbonyl or the like and is selected within a given range of carbon atoms.

Alkoxyalkoxycarbonyl may be methoxymethoxycarbonyl, ethoxymethoxycarbonyl, propyloxyniethoxycarbonyl, i-propyloxymethoxycarbonyl, butyloxymethoxycarbonyl, 2-methoxyethoxycarbonyl, 1-methoxyethoxycarbonyl or the like and is selected within a given range of carbon atoms.

Alkylthioalkoxycarbonyl may be methylthiomethoxycarbonyl, ethylthiomethoxycarbonyl, propylthiomethoxycarbonyl, i-propylthiomethoxycarbonyl, butylthiomethoxycarbonyl, 2-methylthioethoxycarbonyl, 1-methylthioethoxycarbonyl or the like and is selected within a given range of carbon atoms.

Alkylsulfinylalkoxycarbonyl may be methylsulfinylmethoxycarbonyl, ethylsulfinylmethoxycarbonyl, propylsu Ifinylmethoxycarbonyl, i-propylsulfinylmethoxycarbonyl, butylsulfinylmethoxycarbonyl, 2-methylsulfinylethoxycarbonyl, 1-methylsulfinylethoxycarbonyl or the like and is selected within a given range of carbon atoms.

Alkylsulfonylalkoxycarbonyl may be methylsulfonylmethoxycarbonyl, ethylsulfonylmethoxycarbonyl, propylsu Ifonylmethoxycarbonyl, i-propylsu Ifonylmethoxycarbonyl butylsulfonylmethoxycarbonyl, 2-methylsulfonylethoxycarbonyl, 1 -methylsulfonylethoxycarbonyl or the like and is selected within a given range of carbon atoms.

Alkenyloxycarbonyl may be ethenyloxycarbonyl, 1 -propenyloxycarbonyl, 2-propenyloxycarbonyl, 1 -butenyloxycarbonyl, 1 -methyl-2-propenyloxycarbonyl, 2-methyl-2-propenyloxycarbonyl, 1-hexenyloxycarbonyl or the like and is selected within a given range of carbon atoms.

Haloalkenyloxycarbonyl may be 1-chloroethenyloxycarbonyl, 2-chloroethenyloxycarbonyl, 2- fluoroethenyloxycarbonyl, 2,2-dichloroethenyloxycarbonyl, 3-chloro-2-propenyloxycarbonyl, 3-fluoro-2-propenyloxycarbonyl, 2-chloro-2-propenyloxycarbonyl, 4-chloro-3-butenyloxycarbonyl or the like and is selected within a given range of carbon atoms.

Alkynyloxycarbonyl may be ethynyloxycarbonyl, I -propynyloxycarbonyl, 2-propynyloxycarbonyl, 1 -butynyloxycarbonyl, 1 -methyl-2-propynyloxycarbonyl, 2-methyl-2-propynyloxycarbonyl, 1-hexynyloxycarbonyl or the like and is selected within a given range of carbon atoms.

Phenoxycarbonyl having at least one substituent selected from Y on the ring may be 2-fluorophenoxycarbonyl, 2-chlorophenoxycarbonyl, 4-bromophenoxycarbonyl, 4-methylphenoxycarbonyl, 2-methoxyphenoxycarbonyl 3-aminophenoxycarbonyl, 4-trifl uorom ethoxyphenoxycarbonyl 2- methylthiophenoxycarbonyl, 3-trifluoromethylthiophenoxycarbonyl, 4-cyanophenoxycarbonyl, 2-nitrophenoxycarbonyl, 4-trifluoromethylphenoxycarbonyl or the like.

Phenylalkoxycarbonyl and phenylalkoxycarbonyl having at least one substituent selected from Y on the ring may be benzyloxycarbonyl, 2-fluorobenzyloxycarbonyl, 2-chlorobenzyloxycarbonyl, 3- bromobenzyloxycarbonyl, 4-iodobenzyloxycarbonyl, 4-methylbenzyloxycarbonyl, 2- methoxybenzyloxycarbonyl, 4-aminobenzyloxycarbonyl, 4-trifluoromethoxybenzyloxycarbonyl, 2- methylthiobenzyloxycarbonyl, 3-trifluoromethylthiobenzyloxycarbonyl, 2-cyanobenzyloxycarbonyl, 4-nitrobenzyloxycarbonyl, 2-trifluoromethylbenzyloxycarbony, 2-phenethyloxycarbonyl or the like.

Phenoxyalkylcarbonyl and phenoxyalkylcarbonyl having at least one substituent selected from Y on the ring may be phenoxymethylcarbonyl, 2-phenoxyethylcarbonyl, 2-fluorophenoxymethylcarbonyl, 2- chlorophenoxymethylcarbonyl, 4-broniophenoxymethylcarbonyl, 4-methylphenoxymethylcarbonyl, 2- methoxyphenoxymethylcarbonyl, 3-aminophenoxymethylcarbonyl, 4- trifluoromethoxyphenoxymethylcarbonyl, 2-methylthiophenoxymethylcarbonyl, 3- trifluoromethylthiophenoxymethylcarbonyl, 4-cyanophenoxymethylcarbonyl, 2-nitrophenoxymethylcarbonyl, 4-trifluoromethylphenoxymethylcarbonyl or the like.

Alkylthiocarbonyl may be methylthiocarbonyl, ethylthiocarbonyl, propylthiocarbonyl, propylthiocarbonyl, butylthiocarbonyl, i-butylthiocarbonyl, s-butylthiocarbonyl, t-butylthiocarbonyl or the like and is selected within a given range of carbon atoms.

Haloalkylthiocarbonyl may be fluoromethylthiocarbonyl, chlorodifluoromethylthiocarbonyl, bromodifluoromethylthiocarbonyl, trifluoromethylthiocarbonyl, trichloromethylthiocarbonyl, 2,2,2-trifluoroethylthiocarbonyl, 1,1,2,2-tetrafluoroethylthiocarbonyl 2-fluoroethylthiocarbonyl, pentafluoroethylthiocarbonyl or the like and is selected within a given range of carbon atoms.

Monoalkylaminocarbonyl may be methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, i-propylaminocarbonyl, butylaminocarbonyl, s-butylaminocarbonyl, butylaminocarbonyl, t-butylaminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl or the like and is selected within a given range of carbon atoms.

Monohaloalkylaminocarbonyl may be fluoromethylaminocarbonyl, difluoromethylaminocarbonyl, trifluoromethylaminocarbonyl, chloroniethylaminocarbonyl, bromomethylaminocarbonyl, iodomethylaminocarbonyl, 2-fluoroethylaminocarbonyl, 2-chloroethylaminocarbonyl, 3-fluoropropylaminocarbonyl, 2-fluoropropylaminocarbonyl, 1-fluoropropylaminocarbonyl or the like and is selected within a given range of carbon atoms.

Dialkylaminocarbonyl may be dimethylaminocarbonyl, diethylaminocarbonyl, dipropylanlinocarbonyl, di(i-propyl)aminocarbonyl, dibutylaminocarbonyl, di(s-butyl)aminocarbonyl, di(i-butyl)aminocarbonyl, di(t-butyl)aminocarbonyl, dipentylaminocarbonyl, dihexylaminocarbonyl, ethyl(methyl)aminocarbonyl, methyl(propyl)aminocarbonyl or the like and is selected within a given range of carbon atoms.

Di(haloalkyl)aminocarbonyl may be di(fluoromethyaminocarbonyl, di(chloromethyl)aminocarbonyl, di(bromomethyl)aminocarbonyl, fluoromethyl(methyl)aminocarbonyl, chloromethyl(methyl)aminocarbonyl, chloromethyl(ethyl)aminocarbonyl, di(2-fluoroethyaminocarbonyl, (2-fluoroethyl)methylaminocarbonyl or the like and is selected within a given range of carbon atoms.

Phenylaminocarbonyl having at least one substituent selected from Y on the ring may be 2- fluorophenylaminocarbonyl, 2-chlorophenylaminocarbonyl, 4-bromophenylaminocarbonyl, 4- methyiphenylaminocarbonyl, 2-methoxyphenylaminocarbonyl, 3-aminophenylaminocarbonyl, 4- trifluoromethoxyphenylaminocarbonyl, 2-methylthiophenylaminocarbonyl, 3- trifluoromethylthiophenylaminocarbonyl, 4-cyanophenylaminocarbonyl, 2-nitrophenylaminocarbonyl, 4-trifluoromethylphenylaminocarbonyl or the like.

Phenylalkylaminocarbonyl and phenylalkylaminocarbonyl having at least one substituent selected from Y on the ring may be benzylaminocarbonyl, 2-fluorobenzylaminocarbonyl, 2- chlorobenzylaminocarbonyl, 3-bromobenzylaminocarbonyl, 4-iodobenzylaminocarbonyl, 4- methylbenzylaminocarbonyl, 2-methoxybenzylaminocarbonyl, 4-aminobenzylaminocarbonyl, 4- trifluoromethoxybenzylaminocarbonyl, 2-methylthiobenzylaminocarbonyl, 3- trifluoromethylthiobenzylaminocarbonyl, 2-cyanobenzylaminocarbonyl, 4-nitrobenzylaminocarbonyl, 2-trifluoromethylbenzylaminocarbony, 2-phenethylaminocarbonyl or the like.

Alkoxyalkyl may be methoxymethyl, ethoxymethyl, propyloxymethyl, i-propyloxymethyl, butyloxymethyl, i-butyloxymethyl, s-butyloxymethyl, t-butyloxymethyl, pentyloxymethyl, 1 -methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl or the like and is selected within a given range of carbon atoms.

Haloalkoxyalkyl may be fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2-(chrolomethoxy)ethyl or the like and is selected within a given range of carbon atoms.

Alkoxyalkoxyalkyl may be methoxym ethoxymethyl, ethoxymethoxymethyl, propyloxyrnethoxymethyl, i-propyloxymethoxymethyl, butyloxymethoxymethyl, 1 -(methoxymethoxy)ethyl, 2-(methoxymethoxy)ethyl, 2-(ethoxyniethoxy)ethyl, 2-(ethoxy)ethoxymethyl or the like and is selected within a given range of carbon atoms.

Trialkylsilylalkoxyalkyl may be trimethylsilyl methoxymethyl, 2-(trimethylsilyl)ethoxymethyl, 2- (trimethylsilylmethoxy)ethyl, 2-[2-(trimethylsilyl)ethoxy]ethyl or the like and is selected within a given range of carbon atoms.

Hydroxyalkyl may be hydroxymethyl, 1 -hydroxyethyl, 2-hydroxyethyl, 1 -hydroxypropyl, 2- hydroxypropyl, 3-hydroxypropyl, 1 -hydroxy-1-methylethyl, 2-hydroxy-1 -methylethyl, 2-hydroxy-1 1-dimethylethyl or the like and is selected within a given range of carbon atoms.

Phenoxyalky and phenoxyalky having at least one substituent selected from Y on the ring may be phenoxymethyl, 2-fluorophenoxymethyl, 2-chlorophenoxymethyl, 3-bromophenoxymethyl, 4- iodophenoxymethyl, 4-methylphenoxymethyl, 2-methoxyphenoxymethyl, 4-aminophenoxymethyl, 4- trifluoromethoxyphenoxymethyl, 2-methyithiophenoxymethyl, 3-trifluoromethylthiophenoxymethyl, 2-cyanophenoxymethyl, 4-nitrophenoxymethyl, 2-trifluoromethyiphenoxymethyl, 2-(phenoxy)ethyl or the like.

Phenylcarbonyloxyalkoxyalkyl and phenylcarbonyloxyalkoxyalkyl having at least one substituent selected from Y on the ring may be phenylcarbonyloxymethoxymethyl, 2- fluorophenylcarbonyloxymethoxymethyl, 2-chlorophenylcarbonyloxymethoxymethyl, 3- bromophenylcarbonyloxymethoxymethyl, 4-iodophenylcarbonyloxymethoxymethyl, 4- methyiphenylcarbonyloxymethoxymethyl, 2-methoxyphenylcarbonyloxymethoxymethyl, 4- aminophenylcarbonyloxymethoxymethyl, 4-trifluoromethoxyphenylcarbonyloxymethoxymethyl, 2- methylthiophenylcarbonyloxymethoxymethyl, 3-trifluoromethylthiophenylcarbonyloxymethoxymethyl, 2- cyanophenylcarbonyloxymethoxymethyl, 4-nitrophenylcarbonyloxymethoxymethyl, 2- trifluoromethylphenylcarbonyloxymethoxymethyl, 2-(phenylcarbonyloxy)ethoxymethyl, 2- (phenylcarbonyloxymethoxy)ethyl or the like.

Alkylthioalkyl may be methylthiomethyl, ethylthiomethyl propylthiomethyl, i-propylthiomethyl butylthiomethyl, i-butylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, pentylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 2-ethylthioethy, 3-methylthiopropyl or the like and is selected within a given range of carbon atoms.

Haloalkylthioalkyl may be fluoromethylthiomethyl, chloromethylthiomethyl, bromomethylthiomethyl, 2,2,2-trifluoroethylthiomethyl, 2-(chloromethylthio)ethyl or the like and is selected within a given range of carbon atoms.

Phenylthioalkyl and phenylthioalkyl having at least one substituent selected from Y on the ring may be phenylthiomethyl, 2-fluorophenylthiomethyl, 2-chlorophenylthiomethyl, 3-bromophenylthiomethyl, 4-iodophenylthiomethyl, 4-methylphenylthiomethyl, 2-methoxyphenylthiomethyl, 4- aminophenylthiomethyl, 4-trifluoromethoxyphenylthiomethyl, 2-methylthiophenylthiomethyl, 3- trifluoromethylthiophenylthiomethyl, 2-cyanophenylthiomethyl, 4-nitrophenylthiomethyl, 2-trifluoromethylphenylthiomethyl, 2-(phenylthio)ethyl or the like and is selected within a given range of carbon atoms.

Phenylalkylthioalkyl and phenylalkylthioalkyl having at least one substituent selected from Y on the ring may be benzylthiomethyl, 2-fluorobenzylthiomethyl, 2-chlorobenzylthiomethyl, 3-bromobenzylthiomethyl, 4-iodobenzylthiomethyl, 4-methylbenzylthiomethyl, 2-methoxybenzylthiomethyl, 4-aminobenzylthiomethyl, 4-trifluoromethoxybenzylthiomethyl, 2-methylthiobenzylthiomethyl, 3- trifluoromethylthiobenzylthiomethyl, 2-cyanobenzylthiomethyl, 4-nitrobenzylthiomethyl, 2-trifluoromethylbenzylthiomethyl, phenethylthiomethyl, 2-(benzylthio)ethyl or the like and is selected within a given range of carbon atoms.

Alkylcarbonylalkyl may be methylcarbonylmethyl, ethylcarbonylmethyl, propylcarbonylmethyl, i- propylcarbonylmethyl, butylcarbonylmethyl, i-butylcarbonylmethyl, s-butylcarbonylmethyl, t- butylcarbonylmethyl, pentylcarbonylmethyl, 1-(methylcarbonyl)ethyl, 2-(methylcarbonyl)ethyl, 2- (ethylcarbonyl)ethyl, 3-(methylcarbonyl)propyl or the like and is selected within a given range of carbon atoms.

Haloalkylcarbonylalkyl may be fluoromethylcarbonylmethyl, chioromethylcarbonylmethyl, bromomethylcarbonylmethyl, 2,2,2-trifluoroethylcarbonylmethyl, 2-(chloromethylcarbonyl)ethyl or the like and is selected within a given range of carbon atoms.

Alkoxycarbonylalkyl may be methoxycarbonylmethyl, ethoxycarbonylmethyl propyloxycarbonylmethyl, i-propyloxycarbonylmethyl, butyloxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyethyl, 3-(methoxycarbonypropyl or the like and is selected within a given range of carbon atoms.

Haloalkoxycarbonylalkyl may be fluoromethoxycarbonylmethyl, chloromethoxycarbonylmethyl, bromomethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 2-(chloromethoxycarbonyl)ethyl or the like and is selected within a given range of carbon atoms.

Alkoxycarbonyloxyalkyl may be methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, propyloxycarbonyloxymethyl, i-propyloxycarbonyloxymethyl, butyloxycarbonyloxymethyl, 2-methoxycarbonyloxyethyl, 2-(ethoxycarbonyloxy)ethyl, 3-(methoxycarbonyloxy)propyl or the like and is selected within a given range of carbon atoms.

Monoalkylaminocarbonyloxyalkyl may be methylaminocarbonyloxymethyl, ethylaminocarbonyloxymethyl, propylaminocarbonyloxymethyl, i-propylaminocarbonyloxymethyl, butylam inocarbonyloxymethyl, 2-(methylaminocarbonyloxy)ethyl, 2-(ethylaminocarbonyloxy)ethyl, 3- (methylaminocarbonyloxy)propyl or the like and is selected within a given range of carbon atoms.

Dialkylaminocarbonyloxyalkyl may be dimethylaminocarbonyloxymethyl, diethylaminocarbonyloxymethyl, ethyl(methyl)aminocarbonyloxymethyl, methyl(propyl)aminocarbonyloxymethyl, butyl(methyl)aminocarbonyloxymethyl, 2- (diethylaminocarbonyloxy)ethyl 2-{ethyl(methyl)aminocarbonyloxy}propyl or the like and is selected within a given range of carbon atoms.

Phenylaminocarbonyloxyal kyl and phenylami nocarbonyloxyalkyl having at least one substituent selected from Y on the ring may be phenylaminocarbonyloxymethyl, 2- fluorophenylaminocarbonyloxymethyl, 2-chlorophenylaminocarbonyloxymethyl, 3- bromophenylaminocarbonyloxymethyl, 4-iodophenylaminocarbonyloxymethyl, 4- methylphenylam inocarbonyloxymethyl, 2-methoxyphenylaminocarbonyloxymethyl, 4- aminophenylaminocarbonyloxymethyl, 4-trifluoromethoxyphenylaminocarbonyloxymethyl, 2- methylthiophenylaminocarbonyloxymethyl, 3-trifluoromethylphenylaminocarbonyloxymethyl, 2- cyanophenylaminocarbonyloxymethyl, 4-nitrophenylaminocarbonyloxymethyl, 2-trifluoromethylphenylaminocarbonyloxymethyl, 2-(phenylaminocarbonyloxy)ethyl or the like and is selected within a given range of carbon atoms.

Alkyl(phenyl)am inocarbonyloxyalkyl and alkyl(phenyl)aminocarbonyloxyalkyl having at least one substituent selected from Y on the ring may be methyl(phenyl)aminocarbonyloxymethyl, methyl(2- fluorophenyl)aminocarbonyloxymethyl, methyl(2-chlorophenyl)aminocarbonyloxymethyl, methyl(3- bromophenyl)aminocarbonyloxymethyl, methyl(4-iodophenyl)am inocarbonyloxymethyl, methyl(4- methylphenyl)aminocarbonyloxymethyl, methyl(2-methoxyphenyl)aminocarbonyloxymethyl, methyl(4-aminophenyl)aminocarbonyloxymethyl, methyl(4-trifluoromethoxy)phenylaminocarbonyloxymethyl, methyl(2-methylthiophenyl)aminocarbonyloxymethyl, methyl(3-trifluoromethylphenyl)aminocarbonyloxymethyl, methyl(2-cyanophenyl)aminocarbonyloxymethyl, methyl(4-nitrophenyl)aminocarbonyloxymethyl, ethyl(phenyl)aminocarbonyloxymethyl, 2- {methyl(phenyl)aminocarbonyloxy}ethyl or the like and is selected within a given range of carbon atoms.

Alkylsulfinylalkyl may be methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, i-propylsulfinylmethyl, butylsulfinylmethyl, i-butylsulfinylmethyl, s-butylsulfinylmethyl, t-butylsulfinylmethyl, pentylsulfinylmethyl, 1-(methylsulfinyethyl, 2-(methylsulfinyl)ethyl, 2-(ethylsulfinyl)ethyl, 3- (methylsulfinyl)propyl or the like and is selected within a given range of carbon atoms.

Haloalkylsulfinylalkyl may be fluoromethylsulfinylmethyl, chloromethylsulfinylmethyl, bromomethylsulfinylmethyl, 2,2,2-trifluoroethylsulfinylmethyl, 2-(chloromethylsulfinyl)ethyl or the like and is selected within a given range of carbon atoms.

Phenylsulfinylalkyl and phenylsulfinylalkyl having at least one substituent selected from Y on the ring may be phenylsulfinylmethyl, 2-fluorophenylsulfinylmethyl, 2-chlorophenylsulfinylmethyl, 3- bromophenylsulfinylmethyl, 4-iodophenylsulfinylmethyl, 4-methylphenylsulfinylmethyl, 2- methoxyphenylsulfinylmethyl, 4-aminophenylsulfinylmethyl, 4-trifluoromethoxyphenylsulfinylmethyl, 2-methylthiophenylsulfinylmethyl, 3-trifluoromethylthiophenylsulfinylmethyl, 2-cyanophenylsulfinylmethyl, 4-nitrophenylsulfinylmethyl, 2-trifluoromethylphenylsulfinylmethyl 2-(phenylsulfinyl)ethyl or the like and is selected within a given range of carbon atoms.

Alkylsu Ifonylalkyl may be methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, i- propylsulfonylmethyl, butylsulfonylmethyl, i-butylsulfonylmethyl, s-butylsulfonylmethyl, t- butylsulfonylmethyl, pentylsulfonylmethyl, 1-(methylsulfonyl)ethyl, 2-(methylsulfonyl)ethyl, 2- (ethylsulfonyl)ethyl, 3-(methylsulfonypropyl or the like and is selected within a given range of carbon atoms.

Haloalkylsulfonylalkyl may be fluoromethylsulfonylmethyl, chloromethylsulfonylmethyl, bromomethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2-(chloromethylsulfonyl)ethyl or the like and is selected within a given range of carbon atoms.

Phenylsulfonylalkyl and phenylsulfonylalkyl having at least one substituent selected from Y on the ring may be phenylsulfonylmethyl, 2-fluorophenylsulfonylmethyl, 2-chlorophenylsulfonylmethyl, 3- bromophenylsulfonylmethyl, 4-iodophenylsulfonylmethyl, 4-methylphenylsulfonylmethyl, 2- methoxyphenylsulfonylmethyl, 4-aminophenylsulfonylmethyl, 4-trifluoromethoxyphenylsulfonylmethyl, 2-methylthiophenylsulfonylmethyl, 3-trifluoromethylthiophenylsulfonylmethyl, 2-cyanophenylsulfonylmethyl, 4-nitrophenylsulfonylmethyl, 2-trifluoromethylphenylsulfonylmethyl, 2-(phenylsulfonyl)ethyl or the like and is selected within a given range of carbon atoms.

Phenylalkylsulfonylalkyl and phenylalkylsulfonylalkyl having at least one substituent selected from Y on the ring may be benzylsulfonylmethyl, 2-fluorobenzylsulfonylmethyl, 2-chlorobenzylsulfonylmethyl, 3-bromobenzylsulfonylmethyl, 4-iodobenzylsulfonylmethyl, 4-methylbenzylsulfonylmethyl, 2- methoxybenzylsu Ifonylmethyl, 4-aminobenzylsulfonylmethyl, 4-trifluoromethoxybenzylsulfonylmethyl, 2-methylthiobenzylsulfonylmethyl, 3-trifluoromethylthiobenzylsulfonylmethyl, 2-cyanobenzylsulfonylmethyl, 4-nitrobenzylsulfonylmethyl, 2-trifluoromethylbenzylsulfonylmethyl, phenethylsulfonylmethyl, 2- (benzylsulfonyethyl or the like and is selected within a given range of carbon atoms.

Phenylalkoxyalkyl and phenylalkoxyalkyl having at least one substituent selected from Y on the ring may be benzyloxymethyl, 2-fluorobenzylcxymethyl, 2-chlorobenzyloxymethyl, 3-bromobenzyloxymethyl, 4-iodobenzyloxymethyl, 4-methylbenzyloxymethyl, 2-methoxybenzyloxymethyl, 4-aminobenzyloxymethyl, 4-trifluoromethoxybenzyloxymethyl, 2-methylthiobenzyloxymethyl, 3- trifluoromethylthiobenzyloxymethyl, 2-cyanobenzyloxymethyl 4-nitrobenzyloxymethyl, 2-trifluoromethylbenzyloxymethyl, 2-phenethyloxymethyl, 1-(benzyloxy)ethyl, 2-(benzyloxy)ethyl or the like and is selected within a given range of carbon atoms.

Alkylcarbonyloxyalkyl may be acetoxymethyl, propionyloxymethyl, butyryloxymethyl, butyryloxymethyl, valeroyloxymethyl, i-valeroyloxymethyl, 2-methylbutyryloxymethyl, pivaloyloxymethyl, heptanoyloxymethyl, 1 -(acetoxy)ethyl, 2-(acetoxy)ethyl, 2-(propionyloxy)ethyl, 3-(acetoxy)propyl or the like and is selected within a given range of carbon atoms.

Phenylcarbonyloxyalkyl and phenylcarbonyloxyalkyl having at least one substituent selected from Y on the ring may be phenylcarbonyloxymethyl, 2-fluorophenylcarbonyloxymethyl, 2- chlorophenylcarbonyloxymethyl, 3-bromophenylcarbonyloxymethyl, 4-iodophenylcarbonyloxymethyl, 4-methyl phenylcarbonyloxymethyl, 2-methoxyphenylcarbonyloxymethyl, 4-aminophenylcarbonyloxymethyl, 4-trifluoromethoxyphenylcarbonyloxymethyl, 2-methylthiophenylcarbonyloxymethyl 3- trifluoromethylthiophenylcarbonyloxyniethyl, 2-cyanophenylcarbonyloxymethyl, 4-nitrophenylcarbonyloxymethyl, 2-trifluoromethylphenylcarbonyloxymethyl, 2-(phenylcarbonyloxy)ethyl or the like and is selected within a given range of carbon atoms.

Dialkylaminothio may be dimethylaminothio, diethylaminothio, dipropylaminothio, di(i-propyl)amiriothio, dibutylaminothio, di(s-butyl)aminothio, di(i-butyl)aminothio, di(t-butyamiriothio, dipentylaminothio, dihexylaminothio, ethyl(methyl)aminothio, methyl(propyl)aminothio or the like and is selected within a given range of carbon atoms.

Monoalkylaminoalkyl may be methylaminomethyl, ethylaniinomethyl, propylaminomethyl, i-propylaminomethyl, butylaminomethyl, 2-(methylamino)ethyl, 2-(ethylamino)ethyl, 3-(methylamino)propyl or the like and is selected within a given range of carbon atoms.

Dialkylaminoalkyl may be dimethylaminomethyl, diethylaminomethyl, ethyl(methyl)aniinomethyl, methyl(propyl)aminomethyl, butyl(methyl)aminomethyl, 2-(diethylamino)ethyl, 2- {ethyl(methyl)amino}propyl or the like and is selected within a given range of carbon atoms.

Monoalkylamino may be methylamino, ethylaminc, propylamino, i-propylamino, butylamino, s-butylamino, i-butylamino, t-butylamino, pentylamino, hexylamino or the like and is selected within a given range of carbon atoms.

Di(alkyl)amino may be dimethylamino, diethylamino, dipropylamino, di(i-propyl)amino, dibutylamino, di(s-butyl)amino, di(i-butyl)amino, di(t-butyl)amino, dipentylamino, dihexylamino, ethyl(methyl)amino, methyl(propyl)amino or the like and is selected within a given range of carbon atoms.

Alkylcarbonyloxy may be acetoxy, propionyloxy, butyryloxy, i-butyryloxy, valeroyloxy, i-valeroyloxy, 2-methylbutyryloxy, pivaloyloxy, hexanoyloxy, 2-ethylbutyryloxy, 2-methylvaleroyloxy, 4-methylvaleroyloxy, heptanoyloxy, 2,2-dimethylvaleroyloxy, 2-ethyihexanoyloxy, 2-propylvaleroyloxy, octanoyloxy, nonanoyloxy, 3,5,5-trimethyihexanoyloxy, decanoyloxy or the like and is selected within a given range of carbon atoms.

"R3 and R4 may form a 3-to 7-membered ring together with each other" means that R3, R4 may form cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, epoxy, tetrahydrofuran tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, piperidine or the like containing the carbon attached thereto.

"R5, R6, R7 or R9 may form, together with R5, R6, R7 or R9 on the same carbon, an optionally substituted 3-to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with 01.0 alkyl, 02.

0 alkenyl, 02-Cc alkynyl or cyclo C3.C alky" means that R5, R6, R7 or R3 and R5, R6, R7 or R8 on the same carbon may form cyclopropyl, dichlorocyclopropyl, dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, epoxy, tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, piperidine or the like containing the carbon attached thereto.

"R5, R6, R7 or R9 may form, together with R5, R6, R7 or R8 on a different carbon, an optionally substituted 3-to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with 01.C alkyl, 02.

C alkenyl, C2 -C alkynyl or cyclo 03. C alky" means that R5, R6, R7 or R3 and R5, R6, R7 or R8 on a different carbon may form a linkage such as -OH2 -, -OH2 -OH2-, -OH2 -0012 -, -0-, -0-OH2 -, -S-, -S- OH2-, -NR12-(R12 is 01.06 alkyl, 02.06 alkenyl, 02.06 alkynyl or cycloC3. C alkyl) and -N R12-CH2 - (R12 is the same as defined previously).

or R6 may form a bond together with R5 or on an adjacent carbon" means that a double bond may be formed between the carbon attached to R5 or R6 and the adjacent carbon attached to R5 or R6.

"Y may be C.04 alkylene, halo 01.04 alkylene, 02-04 alkenylene or halo 02.04 alkenylene which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with C -C alkyl, 02.06 alkenyl, 02-06 alkynyl or cyclo 03.06 alkyl) and form a 5-or 6-membered ring together with an adjacent carbon or nitrogen atom on a benzene ring or a heterocyclyl" means that indene, dihydroindene, naphthalene, dihydronaphthalene, tetrahydronaphthalene, benzofuran, dihydrobenzofuran, chromene, chroman, benzothiophene, dihydrobenzothiophene, thiochromene, thiochroman, indole, indoline, quinoline, dihydroquinoline, tetrahydroquinoline, cyclopentapyridine, pyrrolopyridine, naphthylidine, pyrazolopyridine, triazolopyrimidine or the like containing the benzene ring or a heterocyclyl attached toY.

Next, examples of the haloalkylsulfonanilde compounds covered by the present invention are shown in Tables 2 to 14, but the present invention should not be restricted thereto.

The symbols in the tables have the following meanings, and for example, Fh-2-Ol means 2-chlorophenyl.

Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Ph: phenyl group.

TABLE 2

0 0 0 0 0 UNR, U UN & R u_ RG' Rd /R5' R6' o o 0 °Rr 0 0 UNct UNj Uj UNj1R6 wNL R5' P6 R6 R5' o 0 Uj WN5 UN) u:

L / R5'

Rd R" Rd o 0 0 WNR6' UrJ U%N UN

R

Rd R6' 0 0 0 0 uNLtGuNQ UN55 u%NL R6'2 R5' R6' R5 0 0 0 0

UN U

R6' UNJR5' R6 R5' R5' R5' 0 0 0 o U UN5d UN R5 UN R6' UNdR U\JS WNJ. R5 WN}\ UNi\ UN5c.

R6' R' T7R5 s S 5 R6-5 UN1ji6 UNY-\ R5' R' R5' R5' R6

S S S S S S

uNL\ UNo:JRG UNLtfR5' UN5 R6Já

S S S S

UNc5R5! 1:ic5 UNj UN)*Rc' U%NL UNj R5 6.: U is represented by the following formula (26).

Formula (26) R(N2 R3 In the table, the position of a substituent X is represented by the numerals in the formula (26), and for example, 3-F means that the carbon marked with 3 on the benzene ring is substituted with F. R =J 11 F1 F., F5 X CF3 H H H H CF3 TT Me TI TI C F H N4 o M c H CF3 H Mc C H CF1 H Mc CO9 Ft H CF3 H EL H H CF3 H Ft Mc H CF3 H Ft CO2 Ft H CF1 H Pr-n H F-I CF3 H Pr-n Mc H CF3 H Pr i II H CF1 H Pr-i Me H CF3 H Pr-c H H C F H P r -c N4 c H CF3 H Eu-n H H C F H H ii -n M e H CF1 H P,u-i H H CF3 H B r I Mc H CF3 H Ru-s F-I H CF3 H Eu-s Me H CF1 H P,ut H H CF3 H J3u-t Me H CF3 H Buc H H CF3 H Eu-c Mc H CF3 H Pen-n H H CF1 H Pen-n Me H CF3 H Pen-c H H CF3 H Pen-c Mc H CF3 H Hex-n H H C F3 II]I cx n Ni e CF3 H Hex-c H H CF3 H Hex-c Mc H CF3 H Cl H H CF3 H Cl CI H CF4 H Br H H CF3 H Br Br H CF3 H I H H CF3 H F H H CF3 ii C][=CIL IF ii CF3 H CHCH, Me H CF3 H CCH I-I H CF3 H CCH Mc H CF1 H CHICH=CH, H H CF3 H CH, CHCH2 Me H CF3 H CH, CCH H H CF3 H CH2CCH Me H CF3 H CH9CI H H CF. H CH2 CI Me H CF3 H CH,CI CH,C1 H CF3 H CHC13 H H C F If C C 1 TI II CF.1 H CH, F H H CF H CHF, H H CF3 H CF3 H H If CF3 Me II C F i H C F K t H CF3 H CH2CH1CI H H C F H C H 2 0 H H H CF3 H CH9 SMe H H CF3 H CH, SCH9 CI H H CF3 H Ph H H CF:1 H Ph Me H CF3 H Ph2C1 H H C F If P h 2 -Ci Me H C F H P h -3 C II II C F] F P Ii 3 c: M e II CF H P1i1C H H CF3 H Ph-d-CI Me H C F H P h -3 -I H H CF3 Ph 4-F H H CF3 H Ph-2-Me H H CF3 H F h30Me H H CF3 H Fh-4SMe H H CF3 H Ph-3-CN H H CF3 H Ph-4-NC, H H CF3 H Ph-2 CC, Me H H CF3 H Ph-S-NH, FT H C F If P h 4 -P h H H CF3 H Ph-2-OPh H H CF3 H Ph-3-&5Ph H H CF3 H Ph-d-CCNMe, H H CF3 H Ph-2-OH H H CF3 H COMe H H CF3 H COEt H H CF3 H COCH,C1 H H CF3 H CO,H H H CF3 H CO,Me H H C F3 H CC), Me Me H CF3 H CO., Ft H H C F H C (1) 2 H ii -i H H C F 11 C C) Nil Ii 11 CF1 H CONHMe H H CF3 H CONMe, H H C F, 11 CII. Ph 11 11 CF3 H CH0Ph-2-CI H H CF3 H CH2 Ph-3-C1 H H CF3 N CH, i'h-4-C 1 H H CF3 H COP]i H H CF3 II COPII 2-C:: 1 N H CF3 H COFh-3-C H H CF3 N COPH-4-C N N CF3 H OH H H CF3 H OMe H H CF1 N OMe Me H CF3 H OFt H H CF3 H OFt Me H CF3 H SMe H H CF3 H SMe Me H CF3 H SPh H H CF3 H CN H H CF3 H NH, H H CF, H NHMe H H CF3 H NHMc' Mc' H CF3 H NMe, H H CF3 H NMe2 Me H CF3 N -CH3 -O-CH, -H CF3 N -CH) -H CF3 II CII, CC If CF3 N -CH, CF0 H CF3 H -(CH)3-H CF3 II (CTIO) TI CF3 N -(CHI) -H CF3 H H H 3-F C F3 11 II 11 4-F CF3 H H H 5-F CF3 II IT II 6 F C F, 11 II 11 4-C CF3 H H H 5-C] CF, N H H 4-Hr CF3 H H H 4 1 CF3 H H H 4-Me CF3 H H H 5-Me CF3 H H H 4OMe CF3 H H H 4 SMe CF3 H Me H 3-F C-F H M e H 1 -F CF3 H Me H 5F C F H M e H 6 F CF3 H Me H 4C1 CF3 II Me II 5C CF3 H Me H 1-Br CF3 H Me H 41 C F3 H Me H 1-Me CF3 H Me H 5 Mc C Fa II Me II 4 OM e CF3 H Me H 4SMe CF1 LI Me Me 3F CF3 H Me Me 4F CF3 H Me Me 5-F CF3 H Me Me 6F CF3 II Me Me 4 C CF3 H Me Me 5C I CF3 [I Me Me 4Br CF1 H Me Me 4L CF3 H Me Me 4Me CF3 H Me Me SN1e CF3 H Me Me 4OMe CF3 H Me Mc 4 SMe CF3 Me H H H CF3 Me Me H H CF3 Me Me Me H CF3 EL H H H CF3 EL Me H H CF3 EL Me Me H CF3 COMe H H H CF3 COMe Me H H CF3 COMe Me Me H CF3 COMe Ft H H CF3 COMe Ft Me II CF3 COMe P rn H H CF3 COMe P rn Me H CF3 COMe Cl H H CF3 COMe CH CHCHO H H CF3 COMe CH,C1 H H C F C OM e C F H H CF3 COMe CF., Me H CF3 COMe Ph H H CF3 COMe Ph Me H CF3 COMe Ph2C 1 H H CF3 C.OMe Ph3 C I II II CF3 COMe Ph1-C1 H H CF3 COMe COMe H H CF3 COMe CO0 H H H CF3 COMe CO2 Me H H CF3 COMe CONH0 H H CF, (:ON4e CONLJN4e II LI CF3 COMe CONNie H H CF3 COMe OH H H C F C C) NJ e C) N/I e 11 11 CF3 COMe OMe Me H CF3 COMe SMe H H CF3 CONIc SN/Ic Mc N CF3 COMe NHMe H H (:oN4e N1IMe Me CF3 COMe CH2 Ph H H CF3 COMe CH, Ph2C 1 H H CF3 COMe CH0 Ph3C 1 H H CF3 COMe CH2 Ph4C1 H H COMe COP Ii H H CF3 COMe COPh2 CI II II CF3 (:oMe COPh-4C I H N CF3 COMe COP1i1CI H H CF3 COMe CH3 C)CH, H CF3 CON/Ic CH) N CF3 COMe (CH2) H CF COMe CH.2) H CF3 COMe -(CH1) -H CF3 COEL H H H CF3 COT3t Me H H CF3 COE t Me Me H CF3 COLt Me Cl N CF3 COEL Me CO,Et H C F C 0 V t V t H N CF3 COLt Vt Me H CF3 COEL Pt CO2Et H CF3 COP t P rn H N CF3 COEt Prn Mc H CF3 COEt Pri H H CF3 COEt Pr-i Me H CF3 COLt Pr c LI LI CF3 COLt Prc Me N CF, COE L Bun H H CF3 COEL Bun Me H CF3 COEL Bui H H CF3 COE t Bu i Me H CF3 COEL Bus H H CF3 COEt Bus Mc H CF3 COPt Bu-t H N CF3 CCLt L3ut Me N C F C C) E t 13 u e 11 II CF3 COE L Bu-c Mc H CF. COFt Pen-n H H CF. COLt Pen-n Me H CF3 COLt Pen-c H H CF3 COEL Pen-c Me H CF3 COFI Hex-ri H H CF COFt Hex-n Me H CF3 COLt Hex-c H H CE3 COFt Hex-c Mc H CF3 COEL Cl H H CF3 COF I C I C I IF CF..) COLt Cl Me H CF3 COLt Br H H CF3 COEL Br Br H C F CO F 1 1 11 IF CF3 COFt F H H C:. F CO F t C IT = C. 112 If TI CE3 COF t CH CR, Mc H CF3 COE L CCH H H CF3 COFi CCII Me IF CF3 COP t CH2 CH=CH. H H (:F3 COP t CIT2 CIT=CII. Me TI CE3 COFt CH9CCH H H CF3 COEr CH9CCH Mc H CF3 COP t C 112 Cl If 11 CF3 COP t CIT9 Cl Me TI COEt CH2CI CH2CI H CF3 COLt CHCI.J H H CF., COIfl CCI., II ii CF3 COFt CH2 F H H (:F3 COP t ClIP. If TI CE3 CONt CF3 H H CF3 COE CF3 Mc H CF3 COLt CF., Ft TI CF3 COFt CH1CHCI H H CF3 COLt CHOOH H H CF3 COEt CH, SMc H H CF3 COEL CHOSCH9C1 H H C F C C) F t P H H H CF3 COP t Ph Me H CE3 COFt I-'h-2-Cl H H CF3 COE Ph-2 CI Me IF CF3 COFi Ph-3-C I H H CF3 COEL Ph-3 Cl Mc If CF3 COIfl Ph 4-Cl H H CF3 COE Ph-4-Cl Mc H CF3 COEt Ph-2-Hr H H C F CO E L P Ii -3 I II If CF3 C0E L Ph-4 F 1! II CF, COEt Ph-2--Me H H CF3 C0E t Ph3 OMe TI IT CF COPt Ph-4SMe H H CF2 COEt PTi2S02Mc H H CF3 COP t Ph 3-CN H H CF2 COEt Ph-4-N02 H H CF3 COPt Ph-2-CON1e H H CF.} COEt Ph3NH2 H H CF3 COPt Ph-4--Ph H H CF2 COEt Ph-2-OPh H H CF3 COEt Ph-3-SI'h H H CF3 COt Ph4 CONMc0 H H CF3 COP t Ph-2-OH H H CF3 C0Et COMe H H CF3 COEt COEt TI IT CF3 COEL COCH,C1 H H CF3 COEL CO,I-I H H CF3 COEt CO0Me H H C F C 0 E t C 0 2 Ni e M e TI CL COP t CO2 Pt H H (:F3 COEt CO2 Eu-i H H CF3 COPt CONH. H H C F3 Cob: t CON HN'Te H H C F3 Cob: t CONMe 2 H H CF3 (J.OEt CH,Ph H H CF3 COPt CH,PIi-2-CI H H CF3 C.OEL CH,Ph-3-C1 H H CF3 COP t CH, Ph-4-C I H H CF3 COEL COPh H H CF COPt COPh 2-Cl H H CF3 COEt COPh-3--C1 H H CF3 COEt COPh 4-C! H H CF3 COEt OH H H C F COP t ON'le I! II CF3 COE t OMe Me H CF3 COEt OFt H H C F3 COb: t Ob: t Me H CF3 COPt SN-ic H H CF3 COEt SMe Me H CF3, COPt SPH H H CF3 COEL CN H H CF3 COEt NH, H H CF3 COP t NHMe H H CF, COEt NHMe Me H CF3 COEt NMe0 H H CF3 COEt NMe1 Me H CF3 COB L -CH. -O-CH2 -H C F C 0 F (CII 2) 2 [1 CF3 COEr -CH. CCI 2 Fl CF3 COB t -CH0 CF0 H CI-COB t -(CHO J -H CF3 COEt -(CH0) H CF3 COEt (CII,) II CF3 COLt H H 3-F C F CO B t IT Ii 1 -F CF3 COLLt H H 5-F CF3 COIL t H H 6-F CF3 COB t H H 4-Cl C F CO E t II II 5 -C I CF3 COB t H H 4-Br CF3 COLt H H 4-i CF3 COEt H H 4-Me CF3 COEL H H 5-Mo CF3 COEL H H 4 OMe CF3 COEt H H 4SMe C F C 0 B t Me II 3 F CF3 COB t Me H 4-F CF3 COB t Me H 5-F CF3 C:OB t Me H 6-F CF3 COEt Me H 4-Cl CF3 COB 1. Me H 5C I CF3 COLt Me Ii 4 Br C F C 0 B i. Me 11 4 -I CF3 C:OB t Me H 4-Me CF3 COEt lyle H 5-Me CF3 CEB t Me H 4-OMe CF3 COB L Me H 4.SMe CF3 COB t Me Me 3-F CF3 COB t Me Me 4-F CF3 COB t Me Me 5-F CF3 COEL Me Me 6-F CF3 COB 1. Me Me 4 C CF3 COB 1. Me Me 5C I CF3 COB t. Me Me 6-Cl CF3 COEt Me Me 3-Br CF3 COEt Me Me 4-Br CF3 COB t Me Me 5-Br CF3 COEt Me Me 4 1 CF3 COB i. Me Me 4-Me CF3 COB t Me Me 5-Me CF3 COIL t Me Me 4ON4e CF3 COBI. Me Vie 4-SMe C F CO P r n IT Ii IT CF'3 COt'r-n Mc' H H CF3 COPy xx Mc' Mc' II CF3 COP r n F I II It CF3 COPrn Ft Me H CF3 COPrn Prn H H CF'3 Cot' v-n P r-n Me H CF3 COPrn C1 H H CF3 COP rn CH2 CHCH, H H CF3 COPvn CH9 CI H H CF3 COP rn C F3 H H CF3 COPy xx CF3 Mc' II CF3 COP r n Ph II It CF3 COP vn Ph Me H CF3 C0Prn Ph2C H H CF3 COI'v-n I'h-3C H H CF3 COPrn Ph4 CI II It CF3 COP r n COMe H H CF3 COP v n CO9 H H H CF3 COPrn CO,Me H H CF3 COPy-n CONHV H H CF3 COPrn CONHMe H H CF3 COP rn CONNie1 H N CF3 COPrn OH H H CF3 COP rri OMe H H CF3 COP rn OMe Me H CF3 COPvn SMe H H CF3 COP v n SMe Me H CF3 COPrn NHMe H H CF3 COP v-n NHMe Me H CF3 COP rn CH0 Ph H H CF3 COPvn CH,Ph2CI H N CF3 COP r n CIT9 Ph 3 Cl II II CF3 COP rn CH, Ph4Cl H H CF3 COPy-n COPh H H CF3 COP r xx COPF 2C I H H CF3 COPvn COPh3CI H H CF3 COPvn COPh4C H H CF3 COP rn CH2 OCH2 H CF3 COP r xx (CIT2 2 IT CF3 COP vn WH0) a N CF3 COPrn (CH1)4 H CF3 COPrn WHO) 5 H CF3 COI'v-i H H H CF3 COP r I Me H H CF3 COP r I Me Me IT CF, COP r 1 Ft II It CF3 COP r i E1 Me H CF3 COPr-i Pr-n H H CF. COPr-i Pr-n Me H CF3 (TO!-' r i C. II El CF3 COPr-i CH9CHCH1 H H CF3 COPr-i CH1C1 H H CF3 COPr-i CF3 N N CF3 COPr-i CF3 Me H CF3 COPr-i Ph H H CF3 COPr-i Ph Me N CF COPr-i Ph-2C1 H H CF3 COPr-i Ph-S-C! I-I F-I C F C 0 P r -1 P Ii -4 C I II El CF3 (TOP r I COMe N N CF. COPr-i COH N I-f CF3 COP r 1 CO, Me II II CF3 COP r 1 CONII1 II 11 CF.} COPr-i CONHMe H H CF3 COPr-i C0NN1e, N N CF3 COP r 1 OIl II II CF3 COP r-I OMe H H CF.} COPr-i OMe Me H C F (TO P r I SM e II El CF3 COP r -I SMe Me H CF3 COPr-i NHMe H H CF3 COPr-i NHMe Me H CF3 COPrI CH, Ph H H CF3 COPr-j CH3 Ph-2-C1 H H CF3 COPr-i CH2 Ph-S-Cl H H CF3 COPr-i CH,Ph-4-Cl H H CF3 COPr-I COPh H N CF3 COPr-i COPF-2-CI H N CF3 COPr-i COPF-S-C1 H H CF3 COPr-1 COPh-1-C H H CF3 COP r-I -CH -O-CH2 -H CF3 COPr 1 (Cu1) II CF3 COPr-i -(CH2) H CF:} COPrI (CH2) -H C F CO P r 1 (C 112 11 CT F (T o P r c H H N CF3 COP r-e Me H H CF3 COPr-c Me ML' H CF: COPr-c lit H H CF3 (TCP r c F I Me El CF3 COP r-c Pr-n H H CT F 2 C C) P r c P r n lvi e 11 CF2 COPr-c Cl H H (:F3 C:(T)Pr-c C:HIC:H-C:-HI H H CF3 C0Prc CH,C1 H H CF3 COPrc CF3 H H CF. COPrc CF Me H CF3 COPrc Ph H H COP r-c Ph Mc H CF3 COPrc Ph2C H H CE: COPr-c I'h-3C H H CF3 COPrc Plr4Cl H H CF3 COP r c COMe 11 IF CF., COP r c CO2 II If TI CF3 COP rc CO., Me H H CF COP r e COYTI, If TI CF3 COPre CONHMe H H CF3 COP rc CONMe2 H H CF3 COPrc OH H H CF3 COPre OMe H H CF3 COP r c ON/ic Me IF CF3 COPrc SMe H H CF3 COP r e SMe Me If CE3 CEI' r-c NHMe H H CF3 COPr-c NHMc' Mc' H CF3 COP re CH2 Ph H H CF3 COPrc CH9Ph-2C1 H H CE3 COJ'r-e CH2I'h-3-C1 H H CF3 COPrc CU, P1r4C1 H H CF3 COPre COPh H H CF3 COP rc COPIr2 C If IF CF3 COPrc COPh3-CI H H CF.. COPrc COPh1C1 H H CF3 COPrc CH,OC1-1, H CF3 COPr-c -(CH, -H CF3 COP r c (CU9) TI CE3 COI'r-e -(CH1) -H CF3 COPrc (CH,)3 H CF. COBun H H H CF3 COBun Me H H CF3 COBun Me Me H CF3 COBun -(CH,) H CF3 COBu-n -(CH1 -H CF3 COBuc H H H CF3 CORuc Me H H CF3 COP, u e Me Me If CF3 CORe c (CU,) II CF3 COBu-e -(CHO) 3 -H CF3 COBut H H H CF3 COBu t Me H H CE3 COE-Su--t Me Me H CF.3 COB u-t -CH., -O-CH0 -H C F C C) 13 t (c 2) II CF3 CONn t (CHO) H C F CO P e ri ri IT If IT CF3 COPe nn Me H H CF3 COPe n-n Me Me H CF3 COPenn (CH,) H CF3 COPe nri (CR2) 3 H CF3 COHexn H H H CF3 COMe xn Me H H CF3 COMe xn Me Me H CF3 COHex-n -(CH9) 2 H CF3 COHex-n -(CR,) 3 H CF, COCH=CH., H H H CF3 COCHCH, Me H H CF3 COCH(l-l., Me Me H CF3 COCHCH2 -(CH2) -H CF3 COCH=CH, (cH, ) H CF3 COPh H H H CF3 COPh Me If II CF3 CO Ph Me Me H CF3 COPh Ft H H C F C 0 P Ii F t V e H CF3 COPh Prn H H CF3 COPF I r-n Me H CF3 COPh Cl If II CF3 COPh C 119 C1[=C112 II II CF3 COPh CR9 Cl H H CF3 COPh CF3 H H C F C 0 I' h C F M e H CF3 COPh Ph H H CF.3 COPh Ph Me H CF3 COPh Ph2 C I If IT CF3 COPh Ph3-CI H H CF3 COPh Ph-4C 1 H H CF3 COPFI COMe H H CF3 COPF COO H H H CF3 COPh CO, Me H H CF. COPh CONH, H H CF3 CCP h CONIIMe IF II CF3 COI'h CONMe9 H H CF3 C.OPh OH H H CF3 COPF OMe H H CF3 COPh OMe Me H CF3 COPTi SMe H H CF3 COPh SMe Me H CF. COPh NHMe H H CF3 COP h N1[Me Me II CF9 COPF CH, Ph H H CF3 COPh CH9 Ph2C I H H CF1 COPTi CH9PhHC! H H CF3 COPh CIL Ph 4 Cl II IT CF3 COPh COPI3 H H CF1 COPh COPh2C1 H H (:F, C(DPh COPh N Cl II II CF1 COPF COPh-4--Cl H H CF3 COPh CH9 OCH9 H CF3 COPN (CHO) 2 H CF3 COPh (CH2 I H CF1 COPF (CH0)4 H CF3 COPh (CH0)3 H CF3 CO, Me II II IT CF3 CO3 Me Mu H H CF3 CO0 Me Me Me H CF1 CO. Me Ft H H CF3 CO3 Me. F i Me H CF3 CO3 Me Prn H H CF3 CO2 Me Prn Me H CF3 CO. Me Cl H H CF3 (:O9Me CHOCH OH9 I-I I-f CF3 CO3 Me CH9 C I I-I H CF3 CO2 Me CF3 H H CF3 CO3Me CF3 Me H CF4 CO9 Me Ph H H CF3 CO9 Me Ph Me IT CF3 (:02 Me Ph2C H H CF1 CO9 Me Ph3C I H H CF3 (:09 Me Ph 4 Cl II II CF3 CO2 Me COMe H H CF3 CO, Me CO2 H N H CF3 CO2 Me CO3 Me H H CF3 CO,Me CONH2 H H CF3 CO9 Me CONHMe H H CF3 CO9Me CONMe2 H H CF3 CO9 Me OH H H CF3 CO2 Me OMe H H CF3 CO2 Me OMe Me H CF3 CO9 Me SMe H H CF3 CO2 Me SMe Me IT CF3 CO3 Me NHMe H H CF3 CO9 Me NHMe Me H CF3 CO3 Me CH, Ph H H CF. (:09 Me (:H. Ph2(:I H H CF3 CO9 Me (:H. Ph3C1 H H CF.5 CO Mc CH, Ph-ct-C H H CF3 CO4 Mc COPh H H CF'3 CO3 Mc COPh-2C I H H CF3 CO0 Mc COPh 3C] H H CF3 CO,Me C0Ph-4C] H H CF3 CO2 Mc CH3 Oc:H, -H CF3 CO1 Me (CHI) H CF3 CO1 Mc (CHI) $ H CF3 CO3Mc -(CH2) H CF5 CO4 Me -(CHI) -H CF3 CO. Ft H H H CF3 CO1 Ft Mc H H CF5 CO4 Ft Me Me H CF3 CO4 E t Mc Cl H CF3 CC)4 Ft Mc CO4 E t H CF3 CO1 El El H H CF5 CO4 Ft Ft Mc II CF3 CO1 El El CO1 El II C F5 CO4 Ft Pr-n H H CF3 CO4 Ft Prn Mc H CF3 CO3 Ft Pr-i H H CF3 CO4 Ft Pri Mc H CF3 CO0 Ft Pr c H H CF3 CO3 Ft Pr c Mc H CF3 CO1 Ft Ru-n H H CF3 CO4 Ft Bun Mc H CF3 CO9Et 1-3ui H H CF3 CO4EL Bui Mc H CF3 CO. Ft Rns H H CF3 COIFt Bus Me H CF3 CO4Ft But H H CF3 CO4 Et F3u-t Mc H CF3 CO4 EL Buc H H CF3 CC, El Buc Me H CF3 CO3 Ft Pcnn H H CF5 CO3 Ft Penn Me H CF3 CO1 Ft I'cn-c H H CF5 CO5 Ft Pcnc Mc H CF5 CO4FI Hcxn H H Cl3 CO,El Hex n Me II CF3 COIFt Hcxc H H CF3 CO3ILt Hexc Me H C! CO1 F: t C I H H CF3 CO4Ft Cl Cl H CF3 CO. Ft Hr H H CF5 CO4FL Br Br H CF3 CO1 Ft I II II CF3 COEt F H H CF3 CO. Ft CH=CHI H H CF3. CO2 Ft OH OH2 Me H CF CO Ft CCH H H CF2 002 F t CCH Me H CF3 C0 Ft OH2 CH=CH, H H CF3 002 Ft OH2 CHCHO Me H CF3 002 Ft CIT2 C-CIf TI If CF3 0(3 Fl Cf-I2 C CH Me H CF2 CO2FI CHICI H H CF3 002 Ft Cf-I2 Ci Me H CF, 002 Ft CIII C I CIT2 C:. i II CF3 CO2Ft CHC]I H H CF2 CO2FI CCI3 H H CF3 CO. Ft CH2 F H H CF3 002 Ft CHFO H H CF3 CO. Ft CF3 H H CF3 CO2 Ft CF3 Me H CF1, 002 Ft CF3 E H CF3 CO2Ft CHICHIC1 H H OF, CO Ft CIT2 CII II If CF3 002 Ft OH2 SMe H H CF3 C*O2Ft C1LSC]I7C] ii CF, 002 Ft Ph H H C F1 CO2 Ft Ph Me H CF, 003 Ft Ph2CI H H CF3 CO2Ft Ph 3 CI ii ii CF3 CO2 Ft Ph-i-C I H H CF3 (:0. Ft Ph2Hr H H CF3 CO2Ft Ph-3-f H H CF3 002 Ft Ph4F H H CF2 002 Ft Ph2Me H H CF3 002 Ft Ph 3OMe H H CF3 C03 Fl Ph4SMe H H CF3 002 Ft Ph 2SO,Me II If CF3 003 Ft Ph3C H H CF3 002 Ft Ph4NO., H H CF3 CO2 Ft Ph2-CO2Me H H CF3 CO2 Ft Ph-3NH9 H H CF3 002 Ft Ph4Ph H H CF3 CO2 Ft Ph-2OPh H H CF3 CO2Et Ph-3-SPh H H CF3 002 Ft Ph4 CONMC2 H H CF3 CO2Ft Ph2OH H H C I C 0 2 F t C C) M e H H CF3 CO2Ft COEt H H C H C (:) 2 F t C 0 C H 2 C I H H CF3 CO2 El CO, H H H CF3 CO2 Ft CO0 Me H H CF3 COIEt CO9Me Me H CF3 CO3 E t CO, E t H H CF3 CO3 Ft CO3 Bu-I H H CF3 COIEt CONHI H H CF3 CO, E t CONHMe H H CF3 CO2 Ft CONMe9 H H CF3 CO, El CH, Ph H H CF3 CO9F:t CH9Ph-2-CI H H C F CO F t C 112 P h 3 C 1 II II CF3 CO2 Ft Cf-I2 Ph-4-CI H H CF3 CO3 E t COPh H H CF3 CO0 Ft COPh-2-C 1 H H CF3 CO2 Ft COPh-3-C1 H H CF3 COIEt COPE 4-Cl H H CF3 CO0 Ft OH H H CF3 CO2 Ft OMe H H CF3 CO1 E t OMe Me TI CF3 CO0 E t OFt H H CF3 CO3 El OE L Me H (:1 CO. Ft SMe II II CF3 CO2 K t SMe Me H CF3 CO3 El SPE H H CF3 CO1 El CN H H CF3 CO9Et NH9 H H CO. Ft NHMe H H CF3 CO0 F t NHMe Me H CF3 CO9 Ft NMe, H H CF3 CO., Ft NMe 2 Me H CF3 (:02 F I -OH0 -0-OH, H CF3 CO9 Ft (OHI) 2 H CF3 CO2Ft -CH2CCI1-H CF3 CO0 E I -CH, CF, -H CF CO2 Ft (CH2) H CF3 CO,El -(CH9)4--H CF3 CO3 Ft -(OH,)5--H CF3 CO2 E t H H 3-F CF3 CO. Ft H H 4-F CF, (:02 Ft H H 5-F C F C C) 2 F t II II 6 -F CF3 CO2 Ft H H 4-C] CF3 CO. Ft H H 5-Cl CF3 Ca, K t H H 4-Br CF3 CO2 Ft H H 4-1 CF3 CO, E t H H 4-Me CF3 CO3EI H H 5 Me C F.1 (() Ft H H I -OMe CF.} CO0 El. H H 4SMe CF2 CO, E I. Me H 3 F CF.} CO0 E t Me H 1-F CF. CO2 Et Me H 5-F CF2 CO, El Me H 6-F CF3 CO0 El Me H 4-Cl CF. CO,Et Me H 5-Cl CF3 CC, El Mc' H 4-Br CF3 Co, E. vIc' II 4 T CF3 CO, Et Me H 4-Me CF3 CO2 El Mc' H SMe CF3 CC, El Me II 4-OMe CF3 CO2 El Me H 4SMe CF2 CO2 El Mc' Mo 3-F C F (:0 E I Me M e 4 F CF2 CO0 El Me Me 5-F CF2 CO2 El Me Me 6-F Cl'3 (:02 El Me N'le 4-Cl CF2 CO0 El Me Me 5-Cl (:F (:02 El Me Me 4Flr CF3 (:02 El Me Me 4-I CF3 CO2 El Me Me 4 Me CO1 El Me Me 5 m\ie CF3 CO2 El Me Me 4 OMe CF3 CO9 El Me Me 4-SMe CF.} CO0 Pr-n H H H CF3 CO0Pr-n Me H H CF0 CC), Pr-ti Me Me H CF3 CO0Pr-n El H H CF3 CO0 Pr-n El Me H CF. CC), Pr-n Pr-n H H CF3 CO0 Pr-n Pr-n Me H CF3 CO.Pr-n Cl H H CF3 CO2 Pr-n CH, CHCH., H H (:09 Pr n (:112 Ci II II CF3 CCYPr-n CE, H H CF3 CO9 Pr n CF, Me II CF3 CO2 Pr-ri Ph H H C F: C 0, P r ii P h Me IT CF: CO9 Fr-n l-'h-2-C1 H H CF, C'O2Pr-n Ph-S-Cl H H CF3 CO0 Pr-n Ph-4-Cl H H C F 2 C C) 2 P r n C CM e II II CF3 CO2 Pr-n CC, H H H CF3 CO2Pr-n C0,Me H H Lb3 CO. Pr-n (:ONH. H H CF3 CO2 Prn CONHMe H H (T*F CO, Prn CONMe, H H CF3 CO2 Pr-n OH H H (TV3 CO. 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Ru-i Ph-4-C1 H H CC1F2 CO9 Eu-i COMe H H CCIF9 Rn-i CO9Me H H CC]FO CO., Eu-i ON-to H H CCI F2 CO., Eu-i OMe Me H CC1F0 CO9Bu-i SMe H H CC1F2 CO9 Eu-i NHMe H H CCIF0 CO9Hn-i Cf-I,Ph H H C C 1 F 2 C 0., E u i C 112 P h 2 C 1 II II CCIFO CO., Eu-i CH2 Ph-S-Cl H H CC]F2 CO9 Eu-i CH-, Ph--I-Cl H H CC1F, CO9 Eu i COPE II II CC]FO CO2 Eu-i COPh-2-C] H H CC]F9 CO9Eu-i COPF3CI H H CC IF2 CO9 Eu-i COPE1C1 H H CC 1 F2 CO9 Eu i CIT9 0 CIT9 II CC-IF., CO9Hti-i -(CR9)0-H CC]F, CO9Eu-i -(CH9)3-H CC!F9 CO9 Ru-i -(CH9)4-H CC!F9 CO9Hu-i -(CH9)5-H CErF, 1-1 H H H C B r F 2 II lvi e 11 [1 CE r P1 IT Me Me II CBrF2 H Cl H H CBrF, H Ph H H CHrF, H Ph Vie H Cf3rF0 H COMe H H CT3rF2 H CO2Me H H C Hr F H OMe H H CBrF2 H OMe Me H CNrF, H CH, Ph H H CBrF, H COPIi H H CBrF9 II CII, 0 CIII II CII r F9 [I (CIII) TI CBrF0 H (CHI) -H CIIrF2 COEt H H H CBrF0 COEt Me H H CBrF2 COEL Me Me H CBrF, C.OEt Cl H H CBrF2 COEt Ph H H C 13 r F2 COC Ph Me Ti CN r F0 COE I CON/Ic H H CII r F, COE t CO2 Me IT TI Cl/I r F CO Vt OMe H H (:H r F0 COE t OMe Me H CErF0 COEt CHIPh H H CBrF0 COEL COPh H H CII r F., COE i CH2 OCH1 H CBrF0 COEt (CHO) 2 H CHrF9 COEt (CN0)9 H CBrF0 CO,Et H H H CNrF0 CC)9]tT N/Ic II II CBrF0 CO9Et Me Me H CT3rF2 COOEt Cl H H C: H r F 1 C C) 2 E t I' N H H CII r F2 CO9 E t Pit Me H C::HrF2 CO2Et COMe H H CBrF0 COIEL CO0Me H H CHrI1 CC)1 EtT OMe H H CI3rF0 CO9Et OMe Me H CT3rF0 COIEt CHOPh H H CBrF0 CO,Et COPh H H CHrF1 CO9 Et -CH9-O-CH2-H CBrF2 CO2 EL -(CH0) I H C N r F 2 C C) 2 F 1. (C 112) 2 IF CIIrF0 CO0 Bui H H H C13 r F, (:02 Eu I Rile IF II CHrF0 CO9 En-i IR'le Me H CBrF0 CO9Eui Cl H H CBrF, CO0 Eui Ph H H CErF0 C02En-i Ph Me H CBrF, CO,13u-i COMe H H CHiT-', CO,Hu-i CO,Mc H H CBrF, CO, Bui OMc H H C 13 r F 2 C C) 13 n I C) M e M e Ii CR if, CO, Bui CH, Ph H H C 13 r 2 C o 13 1 (. C) P h I I LI CHiP', CO-,Hu-i -CH2-O-CH9-H CBrF9 CO9 Bu-i (CH9) H CHrF2 CC)2Hui (CH1) H CCI,F H H H H CC]2F H Mc H H CC I-, F IT Mc Mc TT CCI9F H Ci H H CC!2F H Ph H H CC!9 F H Ph Mc H CC!2F H COMe H H CC I, F LI CO2 Me LI II CC]2 F H OMe H H CC!, F H OMe Me H CC 12 F H CR, Ph H H CC!1F H COPh H H CC!1] II Cl!. 0 CII, ii CC]2 F H -(CHO) H CC 11 F IT (CIT. ) * II CC!1F COEt H H H CC 12 F COLt Mc H H CC! 2 F COE t Mc Mc H CC!9 F COLt CI H II CC]1F COLt Ph H H CCI, F COLt Ph Mc H CCIIF COLt COMe H H CC!2 F COLt CO9 Mc H H CC!,F COLt OMc H H CC!2F COLt OMe Me H (:CI2l C*CE1 CII2Ph LI LI CCI2 F COLt COI'h H H CC! 2 F COE t CH1 OCH0 -H CCI2 F COLt -(CH2) 2 H CCI2F COLI (Cit2)3 II CC!2F CO2Et H H H CC 12 F CO, Ft Me TI II CC 12 F CD, H t Me Me H CC!2F CO1Et Cl H H CCI,F CO2Ft Ph II II CC]2 F CO2 Ft Ph Mc H CC! 2 F CO2 E t COMe H H CCIIF C021-:t CO2Mc H H CC19F CO,Et OMe H H CC. , F CO2 Ft OMe Me TI CC! 2 F CO1 Ft CH2 Ph H H CCI.JF COEt COPh H H CC!0 F CC9 Ft -Cl-I, -0--Cl-I, F-I CC!,F CO,Ft -(CH,),-H CC1 2 F CO, F t (CU, ) II CCI,F CO,Bu-i H H H CCI,F CO2 P,ii-i Mc H H CC!F CO2 Ru-i Me Me H CC1OF CO,Bu-i Cl H H CC!, F CO9 1-itt-i Ph H H CC12 F CO, Eu-i Ph Me H CC1,F CO Eu-i COMe H H CCI9 F CO2 Biii CO9 Mc H H CCI, F CO1 Eu-i OMe H H CC19 F CO2 Eu-i OMc Mc H CC.10F CC),Bu-i CH,Ph H H CCV,F CO,lIu-i COPh H H CC 1 2 F CO2 B u I CIII C) CU2 TI CC!,F C(T)113u I (Cl!2).

CCIOF CO2 Eu-i -(CH2) 3 H CBr,F H H H H CBr0 F H Me H H C 11 2 Ii II NI e M e II CBr,F H -(CHI) 2 H CE r 2 F II (CII, ) TI CAr9 F CO, Ft H H H CBr.,F CO,Et Mc H H CE r 9 F CO9 Ft Mc Me H CEr,F CO2 EL -(CH2) 2 H CBr,F CO9Ft (CH,)3 H CCI3 H H H H CCI3 H Me H H CC13 H Mc Mc H CC13 H (CII,) 2 II CC! H (CH, ) H CC13 CO2 Ft H H H CCI3 CO2Et Mc H H CC1 CO2 EL Mc Me H CC! I CO2 Ft (CR2) 2 H CCI3 CO,Et -(CH9) H !n Table 2, E-1 to E-12 represent the following structures, respectively. +A0

B-i E-2 E-3 B-4 o 0 Ft * C0,E * J0_ji I t nBLI F-5 F-6 F-7 F-S o * *0M e * I F-9 E-iQ F-li E-12

TABLE 3

0 0 S 0 S S UN( UN_k RUN_k UN_kR UN_kRUN_kR N -R5

N

RE' R6 R&R7' R7'' R-o 0 S o s UNANR5UNAN.R5 UNANR5 UNANR5 UNANR5 U%NXNR5 R7') Rj) K6 L-R6' R7' R6' R6' R6' R7' R7' R7' R6' o s 0 S W N.R5 U NR5 UNN W UNN JcR6 F1 R6' R7 R7' R5' 6' R 7 R6' WN-N UNAN W NR5 WN S ANR5 UNANR5 R>? R7'J) R7'-t1) c1AR6 LyLR6.

R5' R6'" R7' R7' 0 S 0 S N A N -R5 N A N -R5 N N -R5 -N N -RT'RE' R7'R6' R7 U is the same as the above-mentioned formula (26). 11

N X

CF3 H H H H H CF3 H Mc H H H CF3 H EL H H H C F II P r U II 11 CF H OH2 Pr-i H H H CF3 H CH9Prc H H H CF. H OH, CHCHI H H H CF3 H CHgCCH H H H CF3 H CH,OMe H H H C F II Cu9 S.Me II II 11 CF.1 H CH2 CO1 Me i-I H H CF3 H CH Ph H H H CF3 H CH., Ph-2-C I H H H CF3 H OH9 I'h-3-C I H H H CF3 II CII, Ph 4 Cl II IT II CF.1 H Ph H H H CF3 H Ph-2-Cl H H H CF3 H Ph-3-Ci H H H CF3 H Ph-4-C H H H CF3 H COMe H H H CF3 H COPr-c H H H CF3 H CONMe., H H H CF3 H SO9Me H H H CF3 H SOOCF3 H H H CF3 H OO1Et H H H CF3 H H Mc H H CF3 H Me Me H H CF3 IT Ft Me TI 11 C F II Pr c Me; Ii CF3 H CH. Pr-i Mc H H CF1 H OH0 Fre Mc H H CF3 H OH, CHCHI Me H H CF3 II CII C CII Mc IT II CF3 H OH, ON'Ie Me H H CF3 H OH9 SMe Me H H CF3 H OH9 009 Mc Me H H CF3 H CH0Ph Mc H H CF3 H OH9 Ph-2-Cl Me H H CF3 H OH9 Ph3C1 Me H H Cl'3 H OH2 Ph-4-CI Me H H CF3 H Ph Me H H CF3 H Ph-2-C1 Me H H CF3 H Ph-3-Ol Me H H CF3 H Ph-1-C Me H H C F3 H COMe Me H H CF3 H COP i--c Me H H C F II CO NM e, Mc' II II CF3 H SOC, Me Me H H CF3 H SO9 CF3 Me H H CF3 H CO,Et Me H H CF. H H Me Me H CF3 H Me Me Me H CF3 H Ft Me Me H CF3 H Prc Me Me H CF. H CH, Pr i Me Me H CF3 H CH, Prc Me Me H CF3 H CH1CH CH, Me Me H CF3 H CH3 CCH Me Me H CF3 H CH., OMe Me N1e H CF3 TT CTT, SMe Me Me II C F Ii C* C 0 2 NI e M e NI e C V3 H CH, Ph Me Me H CF3 H CFIJ Ph2C1 Me Me H CF3 H CH l'h-3-C! Me Me H CF3 H CH2 Ph4C1 Me Me H CF3 H Ph Me Me H CF3 H Ph2C I Me Me H CF3 H I'h-3-C I Me Me H CF2 H Ph4. 1 Me Me H C F1, H COMe Me Me H CF3 H COPrc Me Me H CF3 H CONMe3 Me N4e H CF3 H SO, Me Me Me H CF3 H SO, CF3 Me Me H CF3 H CO., Ft Me Me H CF3 H H Me Ft H C F3 H Me Me Ft H CF3 H H TVIe Prn H CF3 H Me Me Prn H C F H H NA e I' r -i H CF3 H Me Me Pri H CF3 H H Me Prc H C F3 H Me Me Pr c 11 CF3 H H Me CF3 H CF3 H Me Me CF3 H CF3 H H Me Ph H H Me Me Ph H CF3 H H Ft H H CF3 H Me Ft H H CF3 II IF Ft Ft II CF3 H Mc Ft Ft H C F H H P r n N H CF3 H Mc Pr-n H H CF3 H H Pri H H CF3 H Mc Pri H H CF3 H H Prc H H CF3 H Me Prc H H CF3 II II 3 u n ii IF CF3 I-I N4e Ru-n N H CF3 IT TT flu i II If CF3 H N4c F3u i N H C F II II 3 ii s LI IF C F H M c H u -s H H CF3 H H Bu-t H H CF3 H Me Hut H H CF3 H H Buc H H CF3 H Mc Ru-c N H CF3 H H Pen-n H H C F II N/Ic P c II ii 11 IF CF3 H H Pen-c H H CF3 II Me Pen u II If CF3 H H Hex-n H H C F H N4 e N e x n N H CF3 H H Hex-c H H CF3 H Me Hex-c H H CF3 H H Cl H H CF3 H N4e C I N H CF3 H Ft Cl H H CF3 H H C] C] H CF3 H Mc C] C] H CF3 H H Br H H CF3 H Me Br H H CF3 H H I H H CF3 I-I Me I N H CF3 II IT F II If CF3 H Me F H H CF3 H H F F H CF3 H Me F F H CF3 H H CH=CH H H CF3 H Me CH-CH2 H H CF3 H H CHCH3 Me H CF3 H Mc CH CH9 Mc H CF3 H H C-CIT II II CF3 H Me CCH H H CF3 H H CCH Me H CF3 H Me C=CH Mc H CF3 H H CH2CH=CH2 H H CF3 H Mc CH, CHCHO H H CF3 H H CH, CHCHq Me H CF H Me CH CHCH1 Me H CF3 H H CH2C'CH H H CF3 H N/Ic CH,CCH H H CF3 H H CHQ CCH Me H CF3 H Mc CH9 CCH Mc H CF. H H CHIC H H CF3 II N/Ic CI[.,C 11 11 CF1 H H CH. :: !Ic H CF3 H Mc CH., Cl Mc H CF3 H H CHC 12 H H CF3 H Me CHC1, H H CF3 H H CC!3 H H CF3 H Me CC! H H CF3 H H CHIF H H CF3 II N/Ic CU0 F 11 11 CF3 H H CHFO H H CF3 II Me ClEF, II II CF3 H H CF3 H H CF3 H Mc CF3 H H CF3 H H CH1CHVC] H H CF3 H Mc CHOCH9CI H H CF3 H H CH2OH H H CF3 H Mc CH0OH H H CF, H H CH9 SMe H H CF3 H Mc CH2 SMc H H C* F H H C H 2 S C H 2 C I H H CF3 It N/Ic CII,SC1I9CI U 11 C* F * II II P h II IF C F H N/I c I' H H H CF3 H H Ph2C H H CF3 H Mc Ph2C1 H H CF3 H H Ph3 C It ii CF3 H Me Ph3Cl H H CF3 TI TT Ph 4 C 1 TI TI CF3 H N4e Ph4-C1 H H CF3 H Mc Ph-2Br H H CF3 H Mc Ph-3-I H H CF3 H Me Ph4F H H CF3 H Mc Ph-2Me H H CF3 H Mc PIr3OMc H H CF3 It N4e Ph 4SMe H H CF3 H Mc Ph2SO2Me H H CF3 II Me Ph 3 CY II II CF3 II Me Ph 4NO, II 11 CF3 H Me Ph2CO,Me H H CF3 H Me Fh3 Nil0 H H CF3 H Me Ph4Ph H H CF3 H Me Pkr2 OPF TI TT C F ii Nd e P Li 3 S P 11 H H CF3 N N4e Ph4ON N H CF3 TI TI COMe II Ti C F H Me COMe H H CF3 H H COEt H H CF3 H Me GOVt H H CF3 H H COCHOCI H H CF3 H Me COCH, Cl H H CF3 H H COOH H H CF3 H Me COOH H H C F3 ii ii (T0 Me 11 11 CF3 H Me CO3 Me H H CF3 II II CO, Ft II II CF3 H Me CO2Et H H CF3 H H CONHMe H H CF3 H Me CONHMe N H C F TI TI C C) NM 2 If IT CIH II Me CONMe0 IF ii CF3 H H OFT H H CF3 H Me OH H H CF3 H H OMe H H C F H Me OM e H H CF3 H H SMe H H CF3 H Me SMe H H CF3 H H CN H H CF3 H N'le CN H H CF3 H H NH0 H H C F3 ii Me NiL ii 11 CF3 H H NHMe H H CF3 II Me NIIMe II II CF3 H H NMe, H H C F II Nd e NM e, IF ii CF3 H H -CH. -0-H C F TI Me (:112 0 IT CF3 H H -CH2 -C)-H CF3 H Me CH0 C) H CF3 H H -(CH2)2-H CF3 H Me (CH0) 2 H CF3 H H (CH1)3 H CF3 H Me (CH0) H CF3 H Me H H 3-F CF3 H Me H H i-F CF3 H Me H H 5F CF3 H Me H H6F CF3 II Me II TI 4C I CF3 H Me H H 5-C CF3 H Me H H 4-Br C F H M e H H 4 -I CF3 H Mc' H H 4-Me CF3 H Me H H 5-Me CF3 H Me H H 4 OMe C F Ii N1 e II II 4 S Ni e CF3 lyle H H H H CF3 Me H Me H H CF3 Mc' H Me Mc' H CF3 Mc' Me H H H CF3 Me Me Me H H CF3 Me Me Me Me TI CF COMe H H H H CF3 COMe H Me H H CF3 COMe H Me N4e H C F3 COMe Nb H H H CF3 COMe Me Mc' TI TI CF3 COMe Me Me Me H CF3 COMe H CH9 0 H CF3 COMe Me -CH9 -0-H CF3 COMc' H (CH9)2 H CF3 COMe Me (CH9 H CF3 COMe H (CH9) H CF3 COMe Me -(CH. ) H CF3 COLt H H H H CF3 COLt H Me H H CF3 COE i H Me Mc' H CF3 COEt Mc' H H H CF3 COF I Me Me H H CF3 COLt Me Mc' Me TI COFI SO; CF3 I] LI ii CF3 COEt H Et H H CF3 COLt Me Ft H H CF3 COFt H Ft Me H CF3 COLt Me Ft Me H CF3 COLt H Pr-n H H CF3 COLt Me Pr-n H H CF3 COFt H Fr-n Me H CF3 COLt Me Pr-n Me H CF3 COLt H Cl H H CF3 COLt Me Cl H H CF3 COFt H (:H. CH=CH1 N H CF3 COE t Me CH CH-CH H H CF3 COLt H CH9C H H CF3 COEt Me CHC1 H H CF3 COP t H CF3 H H CF3 COP t Me CF3 H H CF3 COE t H CE3 Me H CF3 COE Me CF3 Me H CF3 COP t H Ph H H CF3 COEt Me [H H H CF3 COLt H Ph Me H CF3 COP L Me Ph Me H CF3 COLt H Ph2CI H H CF3 COEt Me Ph2-C1 H H C F C 0 P t IT P h 3 C II II CF3 COP I N/Ic Ph 3C I H H CF3 COLt H Ph4C1 H H CF3 COLt Me Ph4CT H H CF., COE t H COMe H H CF3 COP t Me COMe II If CF3 COEt H CO1H H H CF. COEt Me CO2H H H CF3 COP t IT CO3 Me II II CF3 COP t Me CO3 Me H H CF3 COP t H CONHY H H CF., COE t Me CONH, H N CF3 COLt H CONHMe H H CF3 COP I Me CONITMe II If CF3 COP I. H CONMe3 H H COEt Me CONMe3 H N CF3 (:01/I I H OH N H CF3 COP t Me OIf II If C.F3 COE t H OMe H H CF3 COLt Me OMe H H C.F3 COP t IT OMe Me If CF3 COP t Me OMe Me H CF3 COLt H SMe H H C.F., COE t Me S)vie N H (IF3 co t H SMe Me H CF3 COP t Me SMe Me H CF3 COE t H NHMe H H CF3 COP Me NHMe H H CF3 COP t H NHMe Me H CF3 COP I. Me NIfMe Me If C F C 0 E t H C H P h H H CF3 COP Me CH3 Ph H H CF., COP t ii CII., Ph 2 C. ii Ii C.F1, COLt N/Ic CH3 Ph2C 1 H H CF3 COLt H CH1 PFr3C1 H H Cl3 COEt N4e (:113 Ph 3 Clii Ii CF3 COEi H CH2 ph4C.I N N CF3 C0E Me CH3Ph4C1 H H CF CONI H COPh H H CF3 COEL Me COPF H H CF1 COFi ii COFFI 2C] H H CF1 CaNt Me COPh-2-CI i-f H CF3 CON i. H COPh-3CI H H CF1 COF t Me COP h-3C I H H CF3 CON H COPh4CI H H CF3 CONi N4e COPF 4C] H H CF1 CON t H Ci-I3 H COEt Me -CH3 -C)-H CF3 CaNt H -(CH9) 2 H CF, COEt Me (CH9)0 H CF3. COE H (cH2) H CF3 COD t Me (CII.) II CF1 COEt Me H H 3F CF1 COLt Me H H 4F CF1 COLt Me H H 5-F CF3 COEL Me H H 6 F CF, CON I N4e H H 4C 1 CF1 COLt Me H H 5Cl CO]Ti Me II II 4hr COEt N'le H H 4-I CF3 COLt Me H H 4Me CF. COEL Me H H 5Me CF3 CC)N I Me II ii 4 OMe CF3 CON I Me H H 4SMe C F I C C) P r n TT TI TI Ti CF3 COPrn H Me H H CF. COPr-n H Me Me H CF1 COP r n Me H H H CF1 COPrn Me Me H H CF3 COP rii Me Me Me H CF1 COPrn H CH1O H CF3 COP r n Me CH9 H CF1 COFr-n H -(CH9) H CF3 COPrn Me -(CH9) 2 H C F C 0 P r ii 11 (Cli 2) 1 COPr n N4e (cli,) II C F C 0 P r i H H H H CF3 COP r -I H Me H H CF3 COPr-H N4e Me H CF. COPr-i Me H H H CF3 COP r I Me Me TI Ii CF1 COPri Me Me Me H CF1 COPri H CH3 H CF3 COPri Me CH, H CF3 COPy i TI (CIT 2 CF3 COI'r-Me -(CH3)0-H CF2 COPr-i H -(CH3)3-H CF3 CCPr I Me (GIL)3 II C F3 COP r -c H H H H CF3 COPrc H Me H H CLH COPr c H Me Me II CF COPr-c Me H H H CF3 COPr-c Me Me H H CF3 (TOPr-c Me Me Me H CF3 COP r c I-I -CH2 -0--H CF3 COPr c Me CH2 0 H CF3 COPr-c H -(CH2)2-H CF3 COPr-c Me -(CH1) H CF3 COPr-c H -(CH1) -H CF3 COPr-c Me -(CH1) H C F C 0 H u n H H H H CF3 COBu-n H Me H H C F CC) B U Ii II lvi e' NI e II CF3 COFiun Me H H H CF3 COBu-n Me Me H H CF3 COB u ii Me Me Me II CF3 COHu-n H -CH, -C)-H CF3 COB u-n Me -CH9 -0-H CF3 COBu-ri H -CH)) 2 H CF3 COB u-n Me -(CH2) H CF3 COUu-n H (CH) H CF3 COB u-n Me -(CH1) -H CF3 COD u-c H H H H CF3 COEu-c H Me H H CF3 COB uc H Me Me H C F CO U u c Me 11 11 ii CF3 COFIu-c Me Me H H CF3 COB u-c Me Me Me H CF3 COUu-c H CHC) H CF3 COB u-c Me -CH1 -0-H CF3 COBu-c H -(CHH2-H CF3 COBu-c Me -(CH2)2-H CF3 COBu-c H -(CH)3-H CF3 COBu-c Me -(CH2)3 -H CF3 COBu-t H H H H CF3 COBu-t N Me H H CF3 COBu-t H Me Me H CF3 GEE ij -t Me H H H CF3 COUn t Me Me II II CF3 COB u-L Me Me Me H CF3 COB u-L H -CH3 -0-H C F * C 013 u L Me C TI 2 C) II CF3 COHut H (CHO). H CF1 COP,ut Me (CH9 H CF2 COBnt H (CH1). H CF1 COBut Me (CH) H CF3 COPenn H H H H CF. COPen-n H Me H H CF. COPe nn H Me Me H C F. COP en-n Me H H H CF1 COPe n-n Me Me H H CF.. COPe nn Me Me Me H CF3 COPe nn N CH0 H CF3 COPe nn Me CH2 H CF3 COPenn H (CH,) , H CF3 COPe nn Me (CH2), H CF3 CCPen nil (Cl!.)3 Ii CF3 COPenn Me -(CH.) H CF1 COlIc x n TI TI TI TI CF. COHe xn H Me H H CF1 COHe xii H Me Me H CF3 COHexn Me H H H CF3 COHexn Me Me H H CF3 COHex-n Me Me Me H CF3 COHexn H CH2O H CF1 COHe x-n Me -CH, -0-H CF1 COlIc x ix II (CU2 2 II CF1 COHex-n Me -(CH1) 2 H CF3 COHexnH (CH.)3 H CF1 COHe xii Me -(CHI), -H CF3 COPh H H H H CF3 COP h H Me H FT CF3 COPh TI Me Me TI (:13 COP h Me II Ii II CF1 COPh Me Me H H CF3 COPh Me Me Me H CF1 COPFx H CH. H CF3 COPh Me CH2 H CF3 COPF H -(CH2) 2 H C F C o P h M e -(C H 2) 2 -H CF3 COPh H -(CH2) H CF1 COPh Me (Cli.) ii CF. CO.Me H H H H CF3 CO. Me TI Me II II CF1 CO2 Me H Me Me H CF1 CO. Me Me H H H CF. CO2 Me Me Me H H CF3 CO2 Me Me Me Me H C F i C O IV! e If C If, 0 TT CF.1 CO2 Me Me -CH, -0-H CF3 CO,Me H -(CH9) -H CF3 CO9 Me Me (C 119) 9 II CF.1 CO9 Me H -(CH2) -H CF3 CO9Me Me (CH9) H CF CO9 Ft H H H H CF3 CO9Ft Me H H H C i CO2 Ft Ft II II 11 CF3 CO9 Ft Pr-c H H H CF3 CO,Fl C.H,Pri H H H CF.. CO9 Ft CH, P re H H H CF3 COFt CH9CH=CH1 H H H CF3 CO. Ft CH2CCH H H H CF3 CO9Ft CH,OMe H H H CO2FI C1I,SMe II LI II CF3 COVEt CH9CO,Me H H H CF3 CO9 Ft CH9 Ph H H H C1H3 CO2 Fl Cl-I2 Ph-2--CI H H H CF.. CO2 Ft CH1P13C1 H H H CF3 CO9 Ft CH1Ph4C1 H H H CF3 CO1 El Ph H H H CF3 CO, Ft Ph 2 Cl II II 11 Cl'3 CO9 Ft Ph 3 CI II I] II CF3 COIFt Fh4Cl H H H CF3 CO9Ft COMe H H H CF3 COVEt COPrc H H H CF3 COIFt CONMe, H H H CF1 CO9Ft SO9Me H H H CF3 CO,Et SO,CF3 H H H CF3 CO. Ft CC, Ft H N H CF3 CO2Et H Mc H H CF3 CO9Et Me Me H H CF:1 CO2Ft Ft Me H H CF3 CO9 Ft Prc Me H H CF3 CO9Ft CH,Fr-i Me H H CF3 CO9Ft CH,Prc Me H H Cl CO2 Ft Cit2 CIICII, Me II II CF3 COVEt CHVCCH Me H H CF3 CO,Et CH,OMe Me H H CF3 CO2 Ft CH, SMe Me H H CF3 CO2 Ft CH, CO2 Me Me H H CF3 CO2 Ft CH, Ph Me H H CF3 CO9 Ft Cit9 Ph 2 Cl Me ii 11 CF3 CO2 Ft CH2 Ph3C1 Me H H CF CO2 Ft CH1Ph4C! Me H H CF. CO2 Ft Ph Me H H CF3 CO9 Ft Ph 2 C Me II II CF.1 CO, Ft Ph3C1 Me H H CF., CO2 Ft Ph4C Me H H CF3 CC), I-LI COMe Me H H CF3 CO2Et COPre Me H H CF3 CO,Ft CONMe2 Me H H CF3 CO9Et S0,Me Me H H (Il3 CO9 Fl SO9CF3 Me LI II CF. CO,Ft CO,FI Me H H C F CO F t it Ni e Me ii CF. CO9 E t Me Me Me H CF3 CO9 Ft EL Me Me H CF3 CO,Ft Prc Me Me H CF3 CO9 Ft C1I,Pr I Me Me TI CF. CO,Ft CH9Prc Me Me H CF3 CO9 El CH9CH CH, Me Me H CF3 CO9 Ft CH9 CCN Me Me H CF3 CO2 Ft CH2OMe Me Me H CF3 CO, Ft CII, SMe Me Me II CF., CO,FI CH, CO9 Me Me Me H CF3 CO., Ft CH, Ph Me Me H CF3 CO., Ft CM, Ph-2Ct Me Me H CF. COVEt CM2 Ph3C1 Me Me H CF3 CO2 Ft CM9 Ph4C1 Me Me H CF3 CO9 Ft Ph Me Me H CF3 CO9 Ft Ph2CI Me Me H CF CO2 Ft Ph3C1 Me Me H CF3 CO9 El Ph4C1 Me Me H CF3 CO2 El COMe Me Me H CF3 CO9 Ft COP rc Me Me H CF3 CO9FI CONMe, Me Me H CF3 CO9 Ft SO9 Me Me Me TI CO2 Fl SO2CF3 Me Me II CF3 CO,Et CO,Et Me Me H CF3 CO9 Ft H Me Ft H CF3 CO2 E t Me Me Ft H CF3 CO,Ft H Me Prn H CF3 CO9 Ft Me Me PrnH CF3 CO2 El H Me Pri H CF3 CO2 Ft Me Me I'r-i H CF3 CO,Ft H Me Pre H CF1. CO9 Ft Me Me Pre H CF3 CO2 Ft H Me CF3 H (.1 CO2 Ft Me Me CF.1 H CF3 CO2 Ft H Me Ph H CF3 CO9 Ft Me Me Ph H CF3 CO, Ft H Ft H H CF3 (109 F L Me EL H H CF9 CO9 Fl. H Ft Ft H CF3 CO2 EL Me Et EL H CF3 CO9 Ft II Pr n II II CF3 CO. Ft Me Pr-n I-I H CF3 CO9Et H Pri H H CF. CO2 Ft Me l'r-i H H CF3 CO9FL H Prc H H C F3 CO9 Ft Me Pr c ii H CF. CO2 Ft H Bun H H CF3 CO. Ft Me Hu-n H H CF3 CO9Et H Bu-i H H CF. CO, Ft Me Bui H H CF3 CO2FL H Bus H H CF3 CO, Ft Me Be S II II CF1 CO,Ft H Fut H H CF3 CO2Et Me But H H CF3 CO9Ft H Buc H H CF3 CO9 EL Me B uc H H CF3 CO, Ft H Penn H H CF3 CO9 E t Me Fe nn H H (*I'. CO2 Ft II Pen c II II CF3 CO. Ft Me Pen-c H H CF3 CO9Et H Hexn H H CF3 CO9 EL ML' He x-ii H H C 13 CO,Ft ii I[ex c ii H CF3 CO2 Ft Me Hexc H H CF3 (102 Ft TI C TI TI (:13 C0211t Me CI H H CF3 CO9Et Ft C H H CF3 CO9 Ft H Cl Cl H CF3 CO2 EL Me Cl Cl H CF3 CO,Ft H Br H H CF1 CO2 Ft Me Br H H CF3 CO9Et H I H H CF3 CO. Ft Me I H H CF3 CO9EL H F H H CF3 CO2 F t Me F II 11 (:. CO2 It t II I I II CF3 CO2 Ft Me F F H CF3 CO9Et H CHCH1 H H CF3 CO9 Ft Me CH-CH2 H H CF3 CO2Et H CH CH, Mc H CF3 CC)9 Ft Me C.11C119 Me II CF3 CO2Ft H C=CH H H CF. CO2 Ft Me CII CH H H CF3 CO2 Ft H CCH Mc H CF3 CO2 Ft Me C=CH Me H CF3 CO0 Ft H CH2CR CH2 H H CF3 CO2 EL Me CH2 CHCHO H H CF3 (:0,Fi II CLI, C]1=C1I, Me IL CF'3 CO.. Ft Me CH2 CR CH.. Me H CF3 CO2 EL H CH,CCH H H CF3 (:0.,Ft Me CII2C-"-ClI LI IL CF3 CO0 E t H CH., CCH Me 1-f CF3 CO2 EL Me CH2 CCH Me H CF3 CO. Ft H CE-f2 C I H H CF3 CO2 IL t Me CH2 C! H H CF'3 CO2Ft H CHOCI Me H CF3 CO. Ft Me CH2 Cl Me H CF3 CO2Et H CHC1. H H CF'3 CO1 Ft Me CHCI, H H CF3 CO2 EL H CCI3 H H CF3 c:O2Ft Me CC!3 H H CF'3 CO2 Ft H CH2 F H H CF3 CO2 IL t Me CIt2 F II If CF3 CO.,Ft H CHF2 H H CF3 CO2 E t Me CHF2 H 1-f CF3 CO9 Et H CF3 II If CF3 CO2 Ft Me CF3 H H CF3 CO2 Et H CH0 CH, Cl H H CF3 CO2Et Me CH2CH2CI H H CF3 CO.Et H CH2OH H H CF3 CO0Et Me CH,OH H H CF3 CO2 EL H CH2 SMe H H CF3 COIEL Me CH2SMe H H CF3 CO0Et H CH2SCI-10C1 H H CF3 CO2EL Me CH2SCH2C1 H H CF'3 CO2 Ft 11 P13 11 II C F3 c:o. Ft Me Ph H H CF3 CO2 EL H Ph-2 Cl II LI CF'3 (:00 Ft Me Ph-2-CI H H CF3 CO2 EL H Ph-3-C 1 H H CF3 CO2 El Me Ph3 C II LI CF3 CO2 Ft H Ph-4-C1 H H CF3 CO2Et Me Ph4C1 H H C F' C 02 F: t M e P h -2 -B r H H CF3 CO2 Ft Me Ph31 H H CF3 CO2 Ft Me Ph4F H H CF'3 CO2 Ft Me Ph-2Me H H CF'3 (:02 Ft Me Ph-3-OMe H H CF'3 (:02 Ft Me Ph 4 SMe LI LI CF3 CO2 E Me Ph-2 Me H H CF3 CO2EL Me Ph-3 CN LI LI CF3 CC)9 Ft Me Ph 4NO3 II II CF3 CO2 Ft Me Ph2CO.,Me H H CF3 CO2Ft Me Ph3NH2 H H CF2 CO9 Ft Me Ph-1-l'h H H CF2 CO9 Ft Me Ph2OPh H H CF2 CO., Ft Me Ph-3-S1'h H H CF2 CO9 E t Mc Ph-4OH H H C F3 CO. Ft 11 COMe 11 11 CF3 CO., Ft Me COMe H H CF3 CO9 Ft H COF i H H CF3 CO., Ft Me COE t H H (:13 -2 Ft Ii C.OCII2C] U CF3 CO.,Ft Mc COCH9C] H H CF3 CO9Ft H CO2H H H Cl3 CO9Kt Me COH H H CF3 CO, F L H CO2 Mc H H CF3 CO9Ft Me CO9Me H H CF3 CO,F H CO9EL H H CF3 CO2 Ft Me CO2 t 1 CF3 CO., Ft H CONHMe H H CF3 CO2 Ft Me CONLIMe II Ii CF3 CO., Ft H CONMc9 H H CF9 CO., Ft Me CONMe 2 H H CF3 CO9Et H OH H H Cl2 CO9 Ft Me OH H H CF3 CO2 F H OMe H H CF3 CO, Ft Mc OMe II IT CF3 CO9Ft H SMe H H (:13 CO2 Ft Me SMe II Ii C F C 0 * F t H C Ni H H CF3 CO2 Ft Me CN H H CO,Ft H NH2 H H CF3 CO9Et Mc NH2 H H CF3 CO9 Ft H NHMc H H CF3 CO2 F Mc NHMc H H CF3 CO,Ft H NMe H H CF3 CO9 Ft Me NMe2 H H CF3 CO9 Ft H CH9 H CF3 CO9 Ft Me CH9 H CF3 CO2 Ft H CH2 H CF3 CO2 EL Mc CH9 0 H C F3 CC),Ft 11 (Cu2).

CF3 CO1Ft Mc (CH1)., H CF3 CO9Et H -(CH2) H C F C 0 2 F t e (C 2) 3 II CF3 CO9Ft Me H H3F CF3 CO9Et Mc H H4F CF3 CO, Ft Mu IT IT 5F CF3 CO0 Ft Me H H 6F CF3 CO0 Ft Mo H H 4C1 CF3 CO9 Ft Mo H H 5C I CF3 CO0 F L Mu H H 4-B r CF3 CO,Ft Mo H H4 I CF3 CO0 Ft Me H H 4-Mo CF3 CO0 Ft Me IT IT 5 Me CF3 CO0 Ft Me H H 4-OMo CF3 CO0 Ft Me IT IT 4SMe CF4 CO0 Pr-ri H H H H CF3 CO2 Pr-n H Me H H CF3 CO1 Pr-n H Mo Mo H CF3 CO2 Pr n Mu IT II II CF3 CO2 Pr-n Mo Me H H CF3 CO9 Pr-n Mo Me Mo H CF3 CE9 Pr-n H CH2 O H CF3 CO0 Pr-n Me -CH0 -0-H CF3 CE0 Pr-n H (CH9) H CF3 CO Pr-n Mo -(CH0) -H CF3 CO2 Pr-n H -(CH9) -H CF3 CO2Pr-nMo -(CH0)3-H CF3 CO2 Pr-i H H H H CF3 CO9 Pr-i H Mc H H CF3 CO. Pr i 11 Mc Me II CF3 CO0 Pr-i Mo H H H CF3 CO2 Pr i Mu Me IT IT CF3 CO0 Pr-i Me Me Me H CF3 CO0 Pr-i H -CH-O-H CF3 CO0 Pr-i Me -CH0-O-H CF3 CO9 Pr-i H -(CHO) H CF3 CO,Pr I Me (Cl!9) II CF3 CO0 Pr-i H -(CHO) 3 H CF3 CO9 Pr i Me (CU9) II CF3 CO0 Bu-n H H H H CF3 CO2 flu-n H Me H H CF3 CO0 F-lu-n H Me Me H CO. B u n Mu IT II II CF3 CO0 B LI-n Mo Me H H CF3 CO, flu-n Mo Me Mo H CF3 CO0 flu-n H -CH, -0-H CF3 CO0 En n Me C]I, C) 1! CF CO0 Flu-n H -(CH4) -H CF3 CO9 flu-n Mu -(CHO) I H 0 3 3 C I C 0 2 n n II ( C II 2 1 II CF3 CO9FIu-nMo -(CH9)3-H CF3 CO0 flu-i H H H H CF3 CO0 flu-i H Me H H CF CO flu-i H Mc Mc H CF3 CO2 Un-i Me H H H CF3 CO2 flu-i Mc Mc H H CF3 CO2 Bu i Me Mc Me II CF3 CO. n I ii C 119 0 ii CF3 CO9 flu-i Mc -CH -0-H CF3 CO2 flu-i H (CH0) 2 H CF3 COKu-iMe -(CH),-H CF3 CO2 Eu-i H (CHo) H CF3 CO9Bu-i Me -(CH0)3--H C F CO B u I-II IT II II CF3 CO9 Bu-t H Mc H H CF3 CO1 Bu-t H Me Me H CF3 CO9 F-lu-t Me H H H CF3 co2 B u -L Me Me H H CO9 lin-t Me Me Me H CF3 CO0 flu-t H -CH, -0-H Cl'3 COBu tMe (:112 0 II CF3 CO2 Hu-t H -(CH9)9-H CF3 CO2 Bu-t Me -(CH0)9-H CF3 CO2flu-tN -(CH0)3-H CF3 CO2Bu-LMe -(CH0)3-H CF3 CO2 Pen-n H H H H (:F3 CO. Pen n II Me II II CF3 CD, I'en-n H Mc Mc H CF3 CO2 Pen-n Me H H H CF3 CO2 l-'en-n Mc Mc H H CF3 CO0 Pen-n Me Me Me H C F 3 CC)2 P e n n II C 112 0 II CF3 CO9 Pen-n Me -CH9-O-H CF3 CO2 Pen-n H -(CH9) 2 H CF3 CO1 Pen-n Me -(CH9) 2 H CF3 CO2 Pen-n H -(CH2) -H CF3 C 09 Pen-u Me -(CHC3-H CF3 F-i H H H H CF3 F 1 ii Me II II CF3 F-i H Me Me H CF3 F-i Mc H H H CF3 F-i Me Me H H CF F I Me Me Me II CF3 F-I H -CH, -0-H CF3 F i Me CII 0 II CF3 F-i H -(CH2) 2 H CF3 F-i Me -(CH9)9-H CF3 F-i H -(Cl-I9)3-H CF3 F-i Me -(CH2) H CF3 CO,Hexn H H H H CF. CO9 Hex-n H Me H H CF3 CO He xn H Me Me H CF3 CO0 Hex-n Me H H H CF3 CO0 Hexn Me Mc H H CF. CO0HexnMe Me Me H CF3 CO0 He xn H CH9 H CF3 CO2HexnMe CHqO H CF3 CO,Hexn H -(CH9)9---H CF3 CO., He xn Me WH9) 2 H CF3 CO2 hex ii IF (CU9) II CF3 CO,Hex-nMe -(CH2)3--H CF., CO2 PT) TI IT TI TI C F.1 CEO Ph H Me H H CF., CO2 Ph H Me Me H CF3 CO9 Ph Me H H H CF. CO9 Ph Me Me H H CF3 CO9 Ph Me Me Me H CF3 CO9 Ph H -CH9 -0-H CF3 CO. Ph Me CH9O I-I CF3 CO2 Ph H -(CR9) -H CF3 CO, Ph Me (CHg) 2, H CF. CO2Ph H (CH3)3 H CF9 COOPh Me (CH3)3 H CF3 COQCHOPhH H H H Cl3 (:02 CH, Ph H Me H El CF3 CO9 CH9 Ph H Me Me H CI'., CO9CIIOPh Me II II II CF3 CO9CHOPh Me Me H H CF3 CO. CTT2 Ph Me Me Me TI CF.,. COCHOPH H CH0O H CF3 CO0 CH2 Ph Me CH9 H CF3 COOCHVPhH (CH9)9 H CF3 CO9 CH2 Ph Me -, (CHO) 2 H Cb3 COOCHYPhR -(CH0)3-H CF3 CO9CH2Ph Me (CH2) H CF9, F-2 H H H H CF3 F 2 II Me II II CF3 E2 H Me Me H CF3 E2 Me H H H CF3 E2 Me Me H H F 2 Me Me Me][ C F3 F2 H CH2 C) H CF3 F2 Me CH2 H CF3 E2 H -(CH9) 2 H (:F3 F2 Me -(CHO) 2 H CF3 F 2 II (CIIO) 3 II CF3 F2 Mc (CH2) H CF3 U-S H H H H CF3 F3 H Me H H C F3 U S II NI e Me II CF3 F3 Mc H H H CF3 F S Me Me 11 IT C F F -S M c M e M e H CF3 F-S H -CH0--O--H C F3 F-S Me -CH -0-H CF3 F-S H -(CH2)2-H CF3 F-S Mc -(CH2)1-H CF3 F-S H -(CH2) H CF3 F-S Mc -(CH1)3-H Cl3 Cit2 ON/Ic II II II IF CF3 CH2 OMe H Nc H H CF3 CII, OMc II Mc Mc If CF3 CH, OMe Me H H H CF3 CH, OMc Mc Mc H H CF3 CH. 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Me Me Me H CF3 COSMe H CH2 H CF3 COSMe Me CH1 H CF3 COSMe H (Cu2) Li CF3 COSMe Me -(CHI) 2 H CF3 COSMe. H (CH, ) H CF3 COSMe Me (CH2 H CF3 COSEt H H H H C. F C C) S F t TI NI e II IT CF3 COSE t H Me Me H CF3 COSE t Me H H H COSEt Me Me H H CF3 COSE L Me Me Me H CF3 COSEt H CH2O H CF3 COSEt Me CIT2 0 H CF3 COSEt H (CH9)2 H CF3.OSEt Me (CH9)2 H CF3 COSEt H (CH2) H CF3 COSEL Me (CH9) H CF3 CH.2 503 Me H H H H CF3 OH., SO, Me H Me H H CF3 CITI SO, Me IT Me Me II CF3 CL-I2 SO, Me Me H H H CF3 CH. SO, Me Me Me H H CF3 CR. 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H H CF3 SO2 CF3 Me l'h-4Cl H H CF3 509CF3 H COMe H H CF.. SO, CF, Me COMe H N CF3 SO2 CF3 H CO9 Me H H CF3 SO, CF3 Me CO2 Me H H CF3 SO, CF3 TI ON/fe IT TI (:1-3 50, CJ3 Me OMe II II CF3 SO, CF3 H OMe Me H CF3 SO, CF3 Me OMe Me H CF3 SO9 CF3 H SMe H H CF3 SO2CF3 Me SMe H N CF3 SO, CF3 H NHMe H H CF3 SO, CF3 Me N1IMe 11 11 CF3 SOICF3 H CHIPh H H CF3 SO2 CF3 Mc CII, Ph II II C F S O C F IT C 112 P li 2 * 1 11 11 I mO, ( b, vIe ( H Ph2( I H H CF3 SO CF3 II OIl2 Ph 3 Cl II II CF SO2 CF3 Me OH0 Ph3C1 H H CF3 SO CF3 H CH9PL-4--CI H H CF3 500 CF3 Me CH0Ph4C FT H CF3 SO2 CF.) H COPh H H CF3 S0 CF3 Me C OPh H H CF3 SO CF3 H COPh2Cl H H CF3 S0 CF3 Me COPh 2 Cl 1.1 ii (2F'3 500CF3 H COPh3-CI H H CF3 SO0CF3 Me COPh 3C] H H SO2 CF3 H COPh4Cl H H CF3 SO0C F3 Me COPh4 CI II Ii CF3 SO2C F3 H CN0 H CF3 SO CF3 Me OTTO 0 II CF3 SOOC*F3 H (CH9)9 H CF3 SOOCF3 Me -(CM0)0-H CF3 SOOCF3 H (CH0)3 H CF3 SOOCFO Me -(CM0)3-H (TIfF, TI II II II II CHF, H H Me H H CHFO H H Me Me H CHFO H Me H H H CHFO H Me Me H H CHF, H Me Me Me H (THF, H H -(OH,),---H CHF, H Me -(OH2)0--H CHFO H H -(OH9)1-H CHFO H Me (OH0) -H CHFO COEr H H H H CHF0 (OE H Me H H CHFO COF H Me Me H C TI F CO F t Me IT TI TI CIIIH (TCF: i, Me Me II [1 CHFO COFT t Me Me Me H CHF, COE t H (OH,) -. H CHF, COE L Me (OHO 2 H OHF, COE H (OH2) 3 -H CHFO COE t Me (C H2) -H CHF, CO0 E t H H H H CHFO 0.02 Ft H Me H H OHF, CO.0 E t H Me Me H CHF, COOEt Me H H H CHF0 CO, EL Me Me H H CHFO CO. Ft Me Me Me H CHFO 002 Ft H -(OH9)0-H CHF0 CO0Et Me (0H0)0 H CHF, CO0 Ft H -(OH,) H CIIFO CO9 E t Me (CIT0) II CO, Bu-i H H H H CHFO CO2 Bu-i H Me H H CHFO CO9 Bu-i i-I Me Me H CHE, CO0 Bu-Me H H H CTIF, CO1 B u I Me Me IT IT CHF2 CO9 Flui Me Me Me H CHF, CO2Bu-i H -(CH,)2--H CIIFO CO9 B LI i Me (CIT9) II UHF, CO2 Bui H (CH,) H UHF, CO0 Bui Me (CH2) N

CCFIH H H H H

C C F 2 IT M e TI TI CCI F, H H Me Me H CCF9 H Me H H H C C F II M e M e Ti ii CCI F, H Me Me Me H CC1FI H H -(CHO) 9 H CC1F1 N Me (CH2) H CCF1H H -(CH0)3-H C C T 2 II N'! (c. 2 3 CC1F9 COEt H H H H C C 1 F C 0 F t IT M e TI IT CCITT2 COF t if Me Me ii CCIF, COLT Me H H H CC iF9 COEt Me Me H H CC iF-, COLt Me Me Me H CC 1 F2 CC) F I II (CIT2) 2 IF CC1F, COLt Me -(CH9) H CC1F9 COLt H (CHO) H CC1FI COFI Me (CH2)3 H CC1F2 COLt H H H H CC1F, CO0Et H Me H H CC1FO CO2 El N Me Me H CC iF2 CO2 Ft Me TI II IT CC1F2 COO Ft Me Me H H CC iF9 CO9 E t Me Me Me H CC iF1 CO9 Ft ii (Cu2) 2 IF CC1F2 CO0 Ft Me -(CHO) 0 H CCIF2 CO9 Ft H (CH2) H CC1F, CO0 Ft Me (CH2) H CCTF, (:C011L1 ill II ii Li CCIFO CO9 flu-i F-I Me H H CC1F, CO0 BLIi H Me Me H CC iF-, CO2 Bui Me H H H CC iF, CO Bu-i Me Me H H CC iF, CO Bu-i Me Me Me H C C 1 F 1 GO, B u i II (Cii) 2 II GOlF0 CO2BuiMe (CH2)9 H GOlF2 CO2Bu-i H (CH2) H GCIF CC)9Ru-iMe -(OH9)3--H GBrF2 H H H H H CBrF, H H Me H H GBrF0 H H Me Me H :* ii r F 2 II Me II LI Ii O B r F H M e M e N H CUr 1 11 Me Me Me II CBrF9 H H -(OH9)1-H CUrE, H Me -(OH2)0-H CBrF0 I-I H -(OH2) -H C B r F 2 TI Me CII 2) 3 TI OBrF, COEt H H N H CBrF, COEt H Me. H H GB r F, COLt H Me Me H GBr b, COLt Me H H H O B r F 2 CC) E t Me NI e II II GB r F, COE t Me Me Me H CBrF9 COEt H -(OH9) 2 H CBrF9 COEt Me (OHI) 2 H CBrF9 COEL H (OH9)3-H CBrF1 COEL Me -(OH2)3-H CUrE, CO, EL H H H H OBrF9 CC, Ft H Me H H GBrF9 00, Ft H Me Me H CUrF GO, Ft Me H H H CBrF2 00, Et Me Me H H GB r F, CO2 F L Me Me Me H CBrF0 CO2Ft H -(OH2),--N CUrE0 C0,Et Mc (OTT,), TI G*UrF2 CO2Ft II (0112)2 II GA r F2 00, E t Me -(OH,) -I-f CBrF, CO1Bu-i H H H H CUrE, 002 Bu-i H Me H H CUrE, CO, Bu-i H Me Me H CBrF, 002 Eu-i Me H H H GBrF, 003 Eu-i Me Me H H CArE9 CO2 Ru-i Me Me Me H CUrE, C0,Bu-i H -(OH9), H CUrE9 009 Bu-i Me -(OH9) 2 H CUrE0 CO,Bu-i H -(OH9) H C B r F C C) 2 A ij I Ni e (0 H 1) 2 H GO1FH H H H H GC1FH H Me H H GO I, F H H Me. Me H CC 12 F Ti Me II IT TI C C 1 F H lvi e lvi e H H CCI F H Me Me Me H CCIOFH H -(CH9)2--H CCI0 F H Me -(CH2 2 -H CCIOFH H -(CH9)3-H CC 12 F H Me -(CH2) -H CC12 F COEt H H H H CC 2 F COEt H Me H H CC12F COEt H Me Me H CC11F COE Me H H H CC 19 F COF t Me Me H H CC 12 F COE L Me Me Me H CCI9F COLt H (C1L), H CCT9 F COEt Me (CH9) 2 H CCI2FCOEt LI (Cu9)3 Ii CC I9FCOFt Me (CH9)3 H CC 12 F CO0 Ft IT IT Ii TI CCIFCC)0Nt H Me H H CCI0 F CO2 Ft H Me Me H CCI F CO., Ft Me H H H CC12F CO0 Ft Me Me H H CCI9FCO,Lt Me Me Me H CC12F CO,Ei H (CH9) 2 H CCI1FCO0E:t Me (CH2)0 H CC 12 F CO0 F t II (CIT0 TI CC12FCOOEt Me (CH2) H CC12F CO2 Be-i H H H H Cd9 F CO2 Bii-i H Me H H CCT0 F CO, Bui H Me Me H CCI2FCO9Bu-iMe H H H CC 12 F CO, Bu I Me Me H H (:C12FC00u3I1 iMe Me Me IF CCI2FCO0BuI H (CH9)0 H CCI9FCO,Bu-i Me -(CH9)9--H CCT.F CO0 Be-i H -(CH,) H CC12F CO,Be-i Me -(CHO) -H CBr2FH H H H H CBr2F H H Me H CBr2FH H Me Me H C B r F H lvi e H H N CBr1 F H Me Me H H CUr F IT Me Me Me TI CBr F H H -(CH) H CBr9FH Me -(CH9)9-H CBr9FH H (CH9) H CUr0 F H Me (CH9) H CBr1FC00EL H H H H C.Fr1l'CO2Li II VIe 1! II CBr2FCO2Lt -1 Me Me H CBr1FCO2EL Me H H H CBr, F CC), Ft Me Me H H CBr1F CO2Et Mc Mc Mc H CBr0FCO9Lt H (CH9)9 H CBr1F CO2 EL Mc (CH9) H CDt F CO, Ft II (CII, ) 11 CDr F GO, E Mc (CH,) 6 H CC]3 H H H H H CC]3 H H Mc H H CCI3 H H Me Me H 0013 H Mc H H H CCI3 H Me Me H H C C 1 H M c M c M c H CC13 II II (0111) 1 H C C 1 11 N4 e (C 112) 2 IF CC13 H H -(OH1) 6 H CC 13 H Me (CHO) 3 H CC]3 CO,Lt H H H H CCI3 CO0Lt H Me H H CC 1 002 E t H Mc Mc H CC 13 CO. Vt Me H H H CC13 002 EL Mc Me H H CC1, CO, Li Me Me Me H CC13 009 EL H -(OH2) 2 H CCI 3 CO2 Li Me (Cl!2) 2 IF CC13 CO2Et F-i -(CH2)3-H CC]3 CO0EL Mc -(OH,)6--H In Table 3, E-1 to E-12 are the same as defined above.

TABLE 4

R" R4 U..N, RtiR" ::: R5"-Tt 6 * R6' R6' R5' U is the same as the above-mentioned formula (26).

R I H, XH N2 N3 N3 N3 N3 N7 N3 H Me H H H Me Me H Me Me H H Me H H Me H Me H Me H H Me Me Me H H H H Me Me H H Me Me II Me II Me II Me Me H Me Me Me H H Me H Me Me Me Me H H II Me El II I] Me Ft H Me Vt H H Me H H Vt H H H Me Me H Me Me H H Ft H H Mc Mc OH H H H II 1)0 rid I] II II

H H -CH H H H

H H -(CH)9--H H H H H -0--H H H H Mc bond H H H H Me CH.) H H H II Me (. 0112) 2 II II II H Me 0 H H H (TOMe Me II II II Me Me (TOM e Me Me H H Me H COMe Me II Me II Me II (TOMe Me Me Me H H H (TOMe Me Me H H Me Me (TOMe Me El Me I] Me Me COMe Me Me Me H H Me (TOMe Me Me Me Me H H (TOMe H bond H H H COMe I-f -CH -H H H COMe H (CH2)2 H H H COMe H -0-H H H COEL Me H H H Me Me (TOE t Me Me II II Me II COE L Me H Me H Me H (TOE t Me Me Me 11 H 11 (TO F.. t Me Me H H Me Me (TOP.. L Me H Me H Me Me (TOE L Me Mc Me H H Mc COLt Me Mc Me Mc H H (TOE t Me H H H Me Ft COLt Me Et H H Me H COEt Ft H H H Me Me COEI Me Me H H lit H COEt Me Me OH H H H COEt H bond H H H

COEI H H H H

COEt H -(CHQ) 2 H H H COEt H -0--H H H COEt Me bond H H H COE t Me CH9 H H H LOFt Me (CHV) H H H COE t Me 0 H H H COP i-n Me H H H Me Me COP r-n Me Me H H Me H COPr-n Me Me Me H H H C C) P r -ii Me H M e H M e H COP r ii Me Me II II Me Me C(F-' fn Me H Me H Me Me COP r -n Me Me Me H H Me COP r n Me Me Me Me II II COPr-n H bond H H H COP c-n H -CH9 -H H H COPr-n H -(CH9) H H H COPr-n H -0--H H H CO P r i lvi c' IT If IT Me Me COP i-i Me Mc' H H Me H COPr-Me Me Me H H H C C) P r I Me H e H e H COP c I Me Me If IT Me Me C C) P r -I M e H M e H M e M e COP r-i Mc' Me Mc' H H Mc' COP r j Me Me Me Me IF II COPr-i H bond H H H COP i-i H -CH -H H H COPrI H (CH9) H H H COPr-i H -0--H H H COPr-c Me H H H Me Me C C) P r -c. M e M e H H M e H COP r c Me Me Me H H H COP r-e Me H Me H Me H COP r e Me Me If II Me Me C C) P r -e Me H M e H M e M e COP r -e Me Mc' Me H H Me COP c e Me Me Me Me IF II COPr-e H bond H H H COPrc H CH9 H H H COPy-c H (CH2) H H H COPr-e H -0--H H H COB U L Mc H H H Mc Mc COf3n-t Me Me H H Me H COB u-t Mc Me Mc H H H COBn-t Me H Me H Me H COB u-L Mc Mc H H Mc Mc COB ii-1. Me H Me H Me Me COHu-t Mc Mc Mc H H Mc COB Lt t Mc Me Mc Mc II II (:.oHi 1. IF bond II II II COBu-r H -CH0 -H H H COHu-t H -(CH2)0--H H H COB u If 0 II TI TI COPrc H (CH2) H H H COPrc H H H H COF'h Mc El H El Mc N4c COPh Mc Me H H Mc H COPh Me Me Me H H H COPh Me H Me H Me H CO Ph Me Me II II Me NI COPE Mc H Mc H Mc Mc COPh Mc Mc Mc H H Mc COPE Me Me Me Me H H COPh H bond H H H

COPF H CH -H H H

CC) P B If (cii II II II

COPB H H H H

CO, Mc Mc H H H Mc Me CO., Me Me Me H H Me H CO2 Me Me Me Me H H H CO0 Me Me H Me H Me H CO, Mc Mc Mc H H Mc Mc CO, Me \le IF Me 1! N4e Me CO, Mc Mc Mc Mc H H Mc CO, Mc Mc Mc Mc Me II II CO2 Me H hon d H H H CO, Me H CH, H H H CO0Me H -(CH2)2--H H H CO,Me H H H H COEL Mc H H H Mc Mc CO, EL Mc Mc H H Mc H CO, Ft Me H Me H Me H CO0 E t Me Me Me TI TI TI CO0 Ft Me Me H H Me Me CO0 Et Mc H Mc H Mc Mc CO2 Et Me Me Me H H Me CO, E t Mc Mc Mc Me H H COLt Me H H H Me Ft 009 EL Me EL H H Me H 009 Er Ft H H H Me Me COLt Me Me H H Et H CO0Et Me Me OH H H H COEt H bond H H H 009 EL H -OH9 H H H CO1Et H -(OH2)1--H H H COLt H -0-H H H CO9Et Me bond H H H 009 E t Me -CH -H H H CO9EI, Me -(OH9) -H H H CO2 E t Me -0-H H H CO Pr-n Me H H H Me Me 009 Pr-n Me Me H H Me H 002 Pr-n Me Me Me H H H CO Pr-n Me H Me H Me H 002 Pr-n Me Me H H Mc' Me CO Pr-n Me H Me H Me Me 009 Pr-n Me Me Me H H Me 002 Pr ii Me Me Me Me II 11 CO Pr n IF bond IF 11 IF 002 Pr-n H -OH2-H H H 009 Pr-n H -(01-il) 2 H H H 009 Pr-n H -0-H H H CO Pr-i Me H H H Me Me 002 Pr-i Me Me H H Me H 009 Pr-i Me Me Me H H H 002 Pr-i Me H Me H Me H 009 Pr i ML' Me II 11 Me ML' C0Pr i Me 11 Me IF Me Me 00, Pr-i Me Me Me H H Me 009 Pr-i Me Me Me Me H H 00, Pr-i H bond H H H 00, Pr-i H -OH9 -H H H CO9 Pr-i H -(OH1) 2 H H H COPr-i H -0-H H H CO Eu-i Me H H H Me Me 009 B LI Me Me H H Me H CO0 Eu-i Me Me Me H H H CO2 Eu-i Me H Me H Me H CO Eu-i Me Me H H Me Me 002 B Li-Me H Me H Me Me 002 B u i Me Me Me H H Me 002 Eu-i Me Me Me Me H H CO9Eu-i H bond H H H 001 Eu -i H -OH9 -H H H CC) 9 U u i IF (0112) 2 II II II C 02 B ii I 11 0 II II II F-i Me H H H Me Me F-i Me Me H H Me H C 1 Me Me Mc 11 11 II F-i Me H Me H Me H F-i Me Me H H Me Me C-i Me H Me H Me Me F-i Me Me Me H H Me F I Me Me Me Me 11 Ii F-i H bond H H H C-i H -CH,-I-I H I-I F-i H -(CT-T9)2-H H H F-i H -C)-H H H (09 B n-I Me H H H Me Me CO2 flu-t Me Me H H Me H CC), flu-t Me Me Me H H H CC), fin-I Me H Me H Me H CO9 flu-t Me Me H H Me Me CO2 Bu-t Me H Me H Me Me CC), fin-t Me Me Me H H Me CCL, fin-t Me Me Me Mc' H H CO9Bu-t H bond H H H CO9Bu-H -CH9-H H H C, C) 2 B ii -I H -(C H) 2 -H H H CC), Bu-t H -0-H H H CO9 P h Me H H H Me Me CC), PH Me Me H H Me H CC)2 Ph Me \4e Me TI IT TI CC)2 Ph Me H Me H Me H CC), Ph Mc Me H H Me Me CO9 Ph Me TI Me II Me Me CC)2 Ph Me Me Me H H Me CC), Ph Me Me Me Me H H CC), Ph 11 1) C) 11(1 II II II CO., Ph H -C-H2-H H H CC), Ph II (GIl9) 2 II II CC), Ph 11 (1) II II II E-2 Me H H H Me Me C-2 Me Me H H Me H E2 Me Me Me H H H E-2 Me H Me H Me H F-2 Me Me H H Me Me F-2 Me H Me H Me Me E-2 Me Me Me H H Me E2 Me Me Me Me H H C-2 H bond H H H E-2 H -CH9-H H H E-2 H -(OH9)1--H H H 0 2 IF (I) Ii II ii E-3 Me H H H Me Me E3 Mo Mo H H Mo H 03 Me Me Me H H H E3 Me H Me H Me H E-3 Me Me H H Me Me Me H Me H Me Me E3 Mo Mo Mo H H lyle Me Me Me Me H H E-3 H bond H H H 0 3 IF GIL LI ii II 0-3 H -(OH2),-H H H E-3 H -C)--H H H 0 II * 0 Ni e VI e 11 11 LI M e RI e OH2 OMo Me Mc H H Mc H OH9 OMo Mc Mc Me H H H Of-I, OMe Me H Me H Me H OH2 OMc Mc Mc H H Mc Mc OH, ONic Mc N Me H Mc Mc OH, ONic Mc Mc Mc H H Mc CII, OMo Mc Mc Me Mc TT II OH, OMe H bond H H H OH9 OMo H -OH9 H H H Cf-I,OMe H (OH2) 2 H H H CH,OMe H -0-H H H GOGH, 01 Mc H H H Mo Mo GOGH1 01 Me Me H H Me H GOGH2 01 Me Me Me H H H GOGH, 01 Me H Me H Me H GOGH, 01 Me Me H H Me Me GOGH2 Cl Me H Me H Me Me GOGH, Cl Me Me Me H H Me GOGH, 01 Mc Mc Me Mc H H GOGH, C I H h C) nil H H H GOGH, 01 H -OH2 -H H H 000H,C1 H -(OH9),-H H H C0GI[2 CI H -0-H H H E-4 Mc' H H H Mc Mc E-4 Mc Mc N H Mc H E4 Mc Mc Mc H H H E-4 Me H Me H Me H E4 Me Me H H Me N-ic 04 Me H Me H Me Me 04 Me N-Ic Me H H Me F4 Me Me Me Me H H E-4 H bond H H H F 4 Ii cii., ii ii Ii E-4 H -(CH2)-H H H E 4 II 0 II II II E5 Me H H H Me Me E-5 Me Me H H Me H [-5 Me Me Me H H H E5 Me H Me H Me H F5 Me Me H H Me Me E-5 Me H Me H Me Me E5 Me Me Me H H Me E5 Me Me Me Me H H F-S H bond H H H E-5 H -Cl-I0--H H H F-S H -(Cl-I0)--H H H F-S H -0--H H H [-(3 Me H H H Me Me E6 Me Me H H Me H F El Me Me vie II iF ii Me H Me H Me H E-6 Me Me H H Me Me F6 Me H Me H Me Me E-6 Me Me Me H H Me F-S Me Me Me Me H H F-S H bond H H H E-6 H -CH-H H H F 6 Ii (Cu0) ii ii Ii F-S H -0-H H H F 7 Me II II II Me Me E7 Me Me H H Me H E7 Me Me Me H H H E-7 Me H Me H Me H [-7 Me Me H H Me Me F-7 Me H Me H Me Me F-7 Me Me Me H H Me [-7 Me Me Me Me H H F-7 H bond H H H E-7 H -CH,-H H H E-7 H -(CH0)0--H H H F-7 H -0--H H H F8 Me H H H Me Me F-A Me Me H H Me H F A Me Me Me IT If TI F 8 Me 11 Me 11 Me 11 F-A Me Me H H Me Me F-A Me H Me H Me Me F8 Me Me Me H H Me E8 Me Me Me Me H H F-S H bond H H H F-S H -OH9--H H H F-S H -(OH2)9--H H H F-S H -0--H H H E-9 Me H H H Me Me F-9 Mc Me H H Mc H F-9 Me Me Me H H H F-9 Me H Me H Me H F-9 Mc Me H H Mc Mc F 9 Mc II Mc II Mc Mc F-9 Me Me Me H H Me E-9 Mc Mc Mc Mc H H F 9 II Ta o 11 ci II II II F-9 H -OH9-H H H E-9 H -(01-11)9-H H H F-9 H -0-H I-I H F-il) Mc H H H Mc Mc F-iD Me Me H H Me H F-ID Mc Me Mc H Id H F10 Mc H Mc H Mc H F 10 Me Me 11 Me Me F-I 0 Mc H Mc H Mc Mc F 10 Mc Me Mc II TI Mc F I 0 Me Me Me Me II II F-ID H bond H H H F-ID H C119 H H H F-iD H -(CH9).-H H H F-ID H -0-H H H F-li Me H H H Me Me F-li Me Me H H Mc H F-Il Me Me Me H H H F-li Me H Me H Me H F-li Mc Me H H Mc Mc F-Il Me H Me H Me Me F-i 1 Mc Me Mc H H Mc F I I Me Me Me Me II F-il H bond H H H F 1 1 II CIII II II II F-il H -(CH9)0-H H H F 11 IT 0 II TI TI F12 Mc H H H Mc Mc F12 Me Me H H Mc H F12 Mc Me Mc H H H F 12 Mc II Mc II Mc IT F-l 2 Mc Me H H Mc Mc F-i 2 Me H Me H Me Me F-I 2 Me Me Me H H Me E1 2 Mc Mc Mc Mc H H EI 2 H bond H H H E-1 2 H -CH2 -H H H E-12 H -(CH2) H H H E-12 H -0-H H H CH, SMc NI c H H H Mc NI c CR2 SMe Me Me H H Me H CH, SMc Mc Mc Mc H H H CH, SMe Me H Me H Me H CH SMc Mc Mc H H Mc Mc CH SMe Me H Me H Me Me CH, SMe Me Me Me H H Me CH, SMe Me Me Me Me H H CH, SMc H bond H H H CH2 SMc H CH., H H H CR2 SMe H -(CH) 2 H H H CH1 SMc H -0-H H H CH, OPh Me H H H Me Me CH, 0I'h Mc Mc H H Mc H Gil2 OPh Me Me Me II II II CII2OPh Me II Me II Me II CH2 OPh Mc Mc H H Mc Mc CH2 0i-'h Mc H Me H Mc Mc CH9 OPh Mc Mc Mc H H Mc CR2 OPh Me Me Me Me H H CH,OPh H bond H H H CH2OPh H -CH1---H H H CH., 0I'h H -(CH1) 2 H H H Gil2 OPh II 0 II II II (:112 OCOMe Me II 11 II Me Me CH9 OCOMc Mc Me H H Mc H CH9 OCOMe Me Me Me H H H CH2 OCOMc Mc H Me H Mc H CH0 OCOMc Mc Me H H Mc Mc CH, OCOMe Me H Me H Me Me CH9 OCOMe Me Me Me H H Me CH, OCOMe Me Me Me Me H H CH, OCOMe H hone1 H H H CH., OCOMe H CH9 -H H H CH9 OCOMc H (CH2 2 H H H CH1 OCOMe H H H H CH, OCOE NIc H H H Mc NIc CH0 OCOE t NIc Me H H Mc H CH2 OCOE t NIc Mc Mc H H H CH9 OCOE t NIe H Me H Me H CH, OCOE t NIe Me H H Me NIe Cl!2 OCOLI Me II Me Ii Me Me CH OCOE t Me Mc' Me H H Me CH., OCOEt Me N/Ic Mc Mc H H CH, OCOEt H bond H H H C.Hq OCOE I H CH0 H H H CH,OCOEt H -(CH,),--H H H CH OCOE I. H -0--H H H COSMe Me H H H Me Me CO SMe Me Me IT II Me IT COSMe Me Me Vie H H H CO SMe Me H Me H Mc H COSMc Mc Me H H Mc Mc CO SMe Me II Me II Me Me COSN4c Mc Mc Mc H H Mc COSMe Me Me Me Me H H COSMe H bond H H H COSMC H CH0 H H H COSMc H -(CHY 2 N H H COSMc H 0 H H H COSE t Me H H H Mc Mc COSEt Mc Me H H Mc H COSE I Me Me Me II II II COSE t Me H Me H Me H COSEt [vie Me II LI Me Me COSE t Me H Me H Me Me COSEt Me Me Me H H Me COSEt Me Me Me Me H H t Li Ii tin ii LI Li LI COSEt H -CH0-H H H COSEt H (CHO) 2 H H H COS K t H -0-H H H CH SO, Mc Me H H H Me Mc CH, SO, Me Me Me H H Me H CW SO, Me Me Mc Me H H H CH, SO, Me Me H Me H Me H Clig SO, Mc 1'vle Mc II II Me Mc' CH, SO, Me Me H Me H Me Me CH, SO, Mc Me Mc Me H H Mc CH, SO, Me Me Me Me Me H H CH, SO,Me H bond H H H CH, SO1 Me H CH, H H H CH,SO,Me H -(CH,) 2 H H H Cl-I, SO, Mc H -0-H H H CH2 SOMe Me H H H Me Me CHg SOMe Mc Mc H H Mc H CH2 SOMe Mc Mc Mc H H H CH0 SOMe Mc H Mc H Mc H CH, SONic [vIe Mc H H Mc Mc CH9 SOMe Me H Me H N4e Me CH, SOMe Me Me Me H H Me CIT9 SOMe Me Me Me Me TI TI CH9 SOMe H bond H H H CH, SOMe H CH, -H H H CH9SOMe H -(GH)--H H H CH, SOMe H H H H CH9 Ph Me H H H Me Me CH2 Ph Me Me H H Me H GIL Ph Me Nd e Me II II II CH2Ph Me H Me H Me H CH2 Ph Me Me H H Me Me CH, Ph Me H Me H Me Me GIL Ph Me Me Me II H Me CH, Ph Me Me Me Me H H C IT 2 P b TI b o ti d TT TI TI CH1I'h H -CH,-H H H CH1Ph H -(CR2)2-H H H CH1Ph H -0--H H H SC)9 CF3 Me H H H Me Me SO9 CF3 Me Me IT II Me II SO2 CF2 Me Me Me H H H SO2 CF3 Me H Me H Me H SO2 CF3 Me Me H H Me Me SO CF3 Me H Me H Me Me SO, CF2 Me Me Me H H Me 509 CF3 Me Me Me Me H H In Table 4, F-i to F-i2 are the same as defined above, and "bond" means that the indicated substituents form a bond between the two carbons attached to them, and when the two carbons lie next to each other, the bond is a double bond, and when the two carbons are separated, the bond is a single bond.

TABLE 5

Formula (28) 6VN Pfivsieal N o 2 N -R [nu P. ( C) -properties I I TI Me Mc 114-116 1-2 C 0 K t V e M e 91-93 1-3 COP r -I Me Mc 67 63 1-4 CO0 lit Me Mc 50 51 I 5 C 0 2 I M e M c resinoid

TABLE 6

Formula (29)

CF

°2.. ,R2 No. R2 If-I H H H tesinolcl 11-2 CO U t H H resinoid 11-3 CC)9 B u-I H H rosinold

TABLE 7

Formula (30)

C F

O2S R2

N

Physical No. R0 R7 R5 R2 R5 R5 W properties rin. p. (°C) 1 111-1 H H H H H H 0 57-59 III -2 C 0 F L H H H H H 0 rcsiitDid lii 3 C () P r n 11 11 11 11 11 () 110 110. 5 111-4 COPr-i H H H H H 0 resiriold 111 0 COB U fl IT If TT 11 TI 0 70-71 111-6 F-4 H H H H H C) 99-100 111-7 COCHCH2 H H H H H 0 rosinoid 111-8 F -5 H H H H H 0 resinoid Iii 9 C 2 C t ii I r ii ii II (1) 86 87 111 -10 CO2 Pr-i H H H H H C) resinoid III II CO2 flu I Ii 11 IT TI TI C) resinoid 111-12 F I H H H H H C) resirioid 111-13 F -3 H H H H H 0 resinoid 111-11 CH, OVJe H H H H H 0 resiticid 111-15 CH2 OCH1 Ph H H H H H 0 resinoid III -16 C] 1 0CC) F I H H H H H 0 resi nci ii 111-17 F-fl H H H H H 0 56-58 111-18 C-H2 Ph H H H H H 0 resinoid 111-19 H H N-ic H H H C) resinoid 111-20 C 0 P r -H Me H H H 0 restitoid 111 21 CO P ii 11 Me If 11 11 106-108 11122 (:*O Ct Ii Me Ii 1] II C) 7371 111-23 CO2 Bn-j H Me H H H C) resinoici 111-24 CO2 E t H Ft H H H 0 resinoid 111-25 H H P r -n H H H C) resinoid 111-26 C OF t H P r -ii H H H 0 resinoid 11127 C.OPr L' II Pr n II II II 0 resinoid 111-28 CO2 Ft H Pr-n H H H 0 61-62 111-29 C 02 B u -H P r -n H H H C) 89 90 111-30 H H P r -I H H H C) resinoid III 31 COg Ft II Pr 1 II II II 0 02-105 111-32 COP t H P r -I H H H 0 resinoid 111-33 COPr-c H Pr-i H H H C) resinoid 111-31 H H Pr-c H H H 0 resinoid 11135 COP L H Pr-c H H H 0 resitloid 11136 COP r-c H Pr-c H H H 0 resiticid III 37 CO., F t H Pr-c H H H 0 resinoid 111 38 CO. F t II CF Ti II II 0 124 125 111-39 H H (3M e H H H 0 resinoid 111 40 CO., F t H O.Me H H H 0 resinoid 111-41 H H OPt H H H 0 resinoid 11142 COEL H OF L H H H (I) resinuid 111 43 CO 2 H 0 F t H H H 0 resi nail 111 41 Ii TI S lvi c II TI TI 0 resi noid III 45 C C) 2 11 S M e II II II C) 79-81 111-46 H H Mc Mc H H 0 52-53 111-47 COMc H Mc Mc H H 0 130-132 111-48 COK t H Mc Mc H H C) 106 107 III 49 CO P r -n H Mc lvi c H H 0 110 III 111-50 CO P r -I H Me Me H H 0 56-58 111-51 CO P r c H Mc Mc H H 0 89 -90 111-52 COB u-n H Me Me H H 0 resinoid 111-53 COB u-c H Mc Mc H H 0 resiiioid 111-51 COPe ti-n H Mc Me H H 0 resinuid III 53 E-4 H Mc Mc H H 0 121 125 111-56 C C) Pb H Ni e NI e H N C) resinoid 111-57 CO2 Me H Me Me H H 0 resinoid 111 58 CO. F t H Me Me H H 0 86-87 111-59 C 02 P r -ii H Mc Mc H H 0 106-107 11160 CO1 Btj-n H Me Me H H 0 6365 Iii 61 P-I H Me Me H H C) resinoid 111-62 CO., B u-i H Mc Mc H H C) resinoid 11163 CO1 Hex n 11 Me Me II II C) resinoid 111-64 Ii -8 H NI c M c H H C) rcsinoid 111-65 F-9 H Mc Mc H H 0 resiiioid III 66 F-i (3 H Me Me H H 0 resiiioid III 67 E 3 H Mc Mc H H 0 89 90 11V68 F I I H NI c Ni c H Ft () resinoid 111-69 C 0 2 P h H M e lvi e H H 0 resinoid 111-70 C 0., C H 2 P 6 H Ni e M e H H C) 84 88 III 71 F-7 H Me Me H H 0 iesinuid 11172 SO0CF., H Me Me H H C) resinoid III 73 H H Mc F L H H 0 resinoid 111-74 COMe H Me lit H N C) resinoid 111-75 COP t H Mc Ft H H 0 resinoid 111 76 COP r -c H Me Ft H H 0 resinoid 111-77 CO, Mc H \lc E' t H H 0 ru,iiiuid III -78 C'. C) E I. H lvi c F I. H H 0 teslitoid 111-79 H Me Ni e H H H 0 resinoid 11180 CO. Ct Me Me [I [I II 0 resinoid 1181 CC)4 Ct (II (:1 II [I II 0 resinoid 111-82 CO. Ft TSr Br H H H 0 resinoi.d [[-83 H C I N4 c H H H () rositicid I [-81 C 0 1 El t C I M e H H H C) resiiiuid [[-85 H CO0 lIt Mc N N H C) resinoid 111-86 H CO0 E I. Ft H H H 0 iesirioid III -87 (IC) 0 F L C: (1)2 F E c H H H (1) n-'sinoiI III 88 II II NI e IVI e NT e II C) resiiinid III -89 C' C) 2 F I. H Ni e Me NI e H 0 tesinnid 111-90 H H Me Me H lvi e 0 resincid 111-91 CO.-) Ft Ft Me Me H Me 0 resincid 1192 ii II Me Me II Oil C) 9395 111-93 CO.-) Ft H Me Me H OH 0 95-96 III -94 H M c N-I c NI c H H 0 resiticid [[-95 CO0 Ct Me Me Me H H 0 resiiiuid [[-96 H H P h H H N C) resincid [97 COO Ct H Ph [1 [1 II 0 iesiricid 111-98 C:OE t H Ph H H H C resincid 111-99 H H (CHO) 0 -H H 0 resinoid 111-100 COLt H -(CH0) 2-H H 0 121-122 III 101 COPr n H (Cii.,)., [I Ii C) 119H20 111-102 CO P r -c H -(C H 2) 2 -H H 0 127-128 111-103 CC-, Ft H (CH9 1 * H H 0 09-72 111-101 CO0 Pr-n H -(CHI 1 -H H 0 resincid 111-105 CO2 Hu-L H -(C:H2 I 1-H H 0 rcsiiicid 111-106 F -8 H -( C H) 0 -H H 0 resinoid [[-107 H H -(CF-i0) -H H 0 resincid III 108 COF t II (C IT. ) . II II 0 102-104 III 109 CC) P r c II (CII 2) I II C) icsincid 111-110 CO2 FL H -(CH2 I 1-H H 0 resittoid 111-111 CO2 B u-i Ft -(CH2 I -H H 0 resinoid 111-112 CO2 Ft -CH., -H H H 0 resinoid 111-113 CO-,, Ft -0-H H H 0 resincid 111 -111 H -C) -N: e H H C) resinoid 111 -115 H H N't c lvi c b o ii ci 0 rusinoid III -116 H H H H H H S 116 118 11TH 17 H H N't c lvi c. H H S rosinoid 111-118 CO9 Ft Ft N-ic Mc H H S resirioid 111-119 H H -CHOCCIIO-H H 0 rcsinoid 111-120 C:O. Ft Ft -CH9 CCI -H H 0 resiroid In Table 7, E-1 to E-11 and "bond" are the same as defined above.

Table 8

Formula (31) CF3 O2SR2 Physical No. K2 K5 K6 Ks Ks N7 kg properties rnL p. (1C) I Tv-i CO1 Ft Me H H H H H iesinoid IV 2 [1 Mc hi e II IF Ii Ii (3d (55 IV-CO9 Ft Me Me H H H H resinoid iv 4 II if Ti ii If b/f II resinoid iv-5 CO2 Ft H H H H Me H resinoid TV-6 H H H H H F t H resinoid iv-7 CC V t H N H H V t I-I resinoid iv 8 CO P r -H H H H F t H resinoid IV-9 CO2 Ft H H H H Ft H resinoid iV-10 CO9 B u-i H H H H Ft H resiiioid Tv-Il H H H H H I' r -n H resinoid IV 12 CO2 F t II IT II IF P r n 11 resinoid iv-13 CO2 F: t H H H H OMe H resixioid IV 14 H H H H H SM e H resinoid iv-15 CO2 Ft H H H H SMe H resinoid IV 16 H H H H H SPh H resinoid IV-17 CC2 Ft H H H H SI'h H resinoid Tv-iS H H H H H C 1 H res maid Iv-19 COy t H H H H C I H resinoid iv 20 CO Ph H H H H C 1 H tesinoid Iv-21 Co. F t H H H H C I H resinoid iv 22 H H H H H B r H rusincid Iv-23 CO. F: t N H H H C IN H resinoid iv 24 H H H H H Me INfo 106108 iv-25 COF t H H H H Me PYle resinoid Iv-26 (:O Ft H H H H lyle Me resinoid iv 27 H H H Me H H H resinoid 1V-28 CO9 Ft H H Me. H H H resiiioid TV 29 H H H OH H H H 102-106 IV-30 CO. lIt H H OMe H H H resmnoid IV 31 II Me Me II If M e 11 resinoicl IV-32 CO El Me Me H H Me H iesinoid

TABLE 9

Formula (32) CF3 O7S R R5 Re Physical No. R2 H5 H6 H5 H5 H6 H3 H7 properties Em. p. (LC)i V-I H H H H H H H H 67-69 V-2 COMe H H H H H H H resinoict V 3 COE t H H H H H H H resirtoict V-4 COP r 11 H H H H H H H resirtoid V 5 COP r c H H H H H H H resiiioid V 6 F 4 11 Il] I II II II II 117-118 VT E12 H H H H H H H 9397 V-S COPh H H H H H H H resirtoid V 9 CC0 Mc H H H H H H H resiiioid V-ID CO,Et H H H H H H H 66-67 V-li F8 H H H H H H H 102-103 V 12 C C) 2 13 ii -I H H H H H H H resinoid V-13 F-3 H H H H H H H resinoid V 14 H Mc H H H H H H icsiiioid V IS COP I Me Il]I 1.1 II II II resinoid V-ifS COf'r-c Mc H H H H H H rcsirioid V-iT CC2 E t Me H H H H H H resinoid V-IS H H H Mc H H H H rosirioid V 19 COMe H H Me H H H H 84 87 V-20 COLt H H Me H H H H 93-95 V 21 C 0 P r c H H M e H H H H resirioid V-22 CO2 Mc H H Mc H H H H rosinoid V 23 CC, L t II II Me II II II II 66 67 V24 CO. B'' i II It Me ii II 11 11 resinoid V 23 C C) E H H B u I. H H H H tosiricid V 26 C C) * E t H I-I H u -I H H H H resinoid V27 CO,Et H H Ph H H H H resinoid V-28 H H H H H Ni e H H resiiioid V 29 COF L H H H H Me H H resinoid V 30 COP r c II II II]l NIe LI II resincid V-31 GO, F t H H H H Me H H resinoict V 32 H H H Me Me H H H 106-108 V33 COMe H H Me Me H H H 113115 V 34 COF L H H Me Me H H H 112 113 V 35 CO P r c II II NI e M e II LI II 131-133 V-36 CO2Kt H H Me Me H H H 87-88 V37 COEt Me Me H H Me Me H resinoid V 38 CO. EL Me Mc H 1-f Mci. Mc H reslitcid V 39 11 ii II II II 11 LI NI e lesi uìn 4 V 40 CO2 F t H H H H H H Me 7F72.5 In Table 9, E-3, E-4, E-8 and E-12 are the same as defined above.

TABLE 10

Formula (33)

C F

O2S. R2

N A N L.J

Physical No. R2 F9 F3 F5 F5 properties I'm p. (t) 1 Yll H H H H H 184-186 VI-2 C 0, C t CO1 F t H H H resinoid VI 3 H SO0 CF3 H H H resinoid V1-1 CO2 Ct SO CE3 H H H 110-111 VIS SO0 CF2 SO0 CF3 H H H resinoid VIH6 H Me H H H 39-91 Vf7 CO1 Ft Me H H H 82 83

TABLE 11

Formula (34) C F3 O2S R2 -Physical No. R9 m np. (Cl properties -VI i-I H 0 resi noi 8 Vii 2 Co E t 0 rosinoid VI 1-3 (2 C) F r c 0 resinoid VII 4 C C) E L 0 resinoid VII 5 CO. B Li 1 0 rPSiYIOiCl VJJ-6 H 2 yes inoid VII 7 CO E 2 resinoid V 11-8 C C) V t 2 resinoid

TABLE 12

Formula (35) CF3 O,S 6Ná Physical N o R 2 m properties [m. . (C, HIf-1 H 2 resinoid Viii 2 C 0, E 1 2 resiiioid

TABLE 13

Formula (36) O2S R, at Physical N o -K propeities j) C) I IX 1 CO Et resinrid

TABLE 14

Formula (37) O2S.R2 :CH2)flR5 N o R R R X n rrn. p. (°C) X I CF II 11 C I I resinoid X2 C F1 H Xl o F I resinod X3 CF3 COL, Et Mo F 1 rosinoid X-4 CHFO H H H 2 resinoid X 3 C C I II Me 11 1 iesinoi! X-6 C F C I 1 H Me H I resi.noid X7 CFC12 CO,Et Mo H 1 rosinoid Thus, for the avoidance of doubt, the invention provides the following mixtures of the compound of formula (I) and a safener: compound of formula (I) + AD 67 (MON 4660), compound of formula (I) --benoxacor, compound of formula (I) -1-cloquintocel-mexyl, compound of formula (I) +cyometrinil, compound of formula (I) + the corresponding (Z) isomer of cyometrinil, compound of formula (I) +cyprosulfamide, compound of formula (I) + dichlormid, compound of formula (I) + dicyclonon, compound of formula (I) + dietholale, compound of formula (I) + fenchlorazole-ethyl, compound of formula (I) + fenclorim, compound of formula (I) + flurazole, compound of formula (I) + fluxofenim, compound of formula (I) + furilazole, compound of formula (I) + the corresponding R isomer of furilazole, compound of formula (I) + isoxadifen-ethyl, compound of formula (I) + mefenpyr-diethyl, compound of formula (I) + mephenate, compound of formula (I) + oxabetrinil, compound of formula (I) + naphthalic anhydride, compound of formula (I) + Tl-35, compound of formula (I) + N-isopropyl-4-(2-methoxy- benzoylsulfamoyl)-benzamide (GAS RN 22 1668-34-4) and the compound of formula (I) + N-(2-methoxybenzoyl)-4-[(methylaminocarbonyamino]benzenesulfonamide.

In a preferred embodiment, the invention provides the following mixtures of the compound of formula (I) and a safener: compound of formula (I) + cloquintocet-mexyl, compound of formula (I) + cyprosulfamide, compound of formula (I) + N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide, compound of formula (I) + isoxadifen-ethyl, compound of formula (I) + benoxacor, compound of formula (I) + dichlormid and the compound of formula (I) + fluxofenim. In a more preferred embociment, the invention provides the following mixtures of the compound of formula (l)and a safener: compound of formula (I) + cloquintocet-mexyl, compound of formula (I) + N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide, compound of formula (I) + benoxacor.

The safeners for use in the invention may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 14th Edition (BCPC), 2006. The reference to cloquintocet-mexyl also applies to cloquintocet and to a lithium, sodium, potassium, calcium, magnesium, aluminiuni, iron, ammoniuni, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in W002/34048 and the reference to fenchlorazole-ethyl also applies to fenchlorazole, etc. Preferably the mixing ratio of mixture of the invention to safener is from 100:1 to 1:10, especially from 20:1 to 1:1.

The present invention also provides a method for protecting crops of useful plants from the harmful effects of a herbicide of formula (I) as defined herein, which comprises applying to the locus of the useful plants at least one safener selected from the group consisting of AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, Tl-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (GAS RN 221668- 34-4) and N-(2-methoxybenzoyl)-4-[(methylami nocarbonyl)amino]benzenesu Ifonamide.

The present invention also provides a method for combating weeds in crops of useful plants, which comprises treating the useful plants, seeds, or cuttings thereof or the locus of the useful plants simultaneously or at separate times with a herbicidally active amount of a compound of formula (I) and at least one safener selected from the group consisting of AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, Tl-35, N- isopropyl-4-(2-methoxy-benzoylsulfanioyl)-benzam ide (GAS RN 221668-34-4) and N-(2-methoxybenzoyl)-4-ftmethylaminocarbonyamino]benzenesulfonamide.

Any method of application to weeds/crop of useful plant, or locus thereof, which is routinely used in agriculture may be used, for example application by spray or broadcast method typically after suitable dilution of the composition of the invention.

The term "herbicide" as used herein means a compound that controls or modifies the growth of plants. The term "herbicidally effective amount" means the quantity of such a compound or combination of such compounds that is capable of producing a controlling or modifying effect on the growth of plants.

Controlling or modifying effects include all deviation from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing and the like. The term "plants" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. The term "locus" is intended to include soil, seeds, and seedlings, as well as established vegetation and includes not only areas where weeds may already be growing, but also areas where weeds have yet to emerge, and also to areas under cultivation with respect to crops of useful plants. "Areas under cultivation" include land on which the crop plants are already growing and land intended for cultivation with such crop plants. The term "weeds" as used herein means any undesired plant, and thus includes not only agronomically important weeds as described below, but also volunteer crop plants.

The compositions for use in the invention can be applied before or after planting of the crops, before weeds emerge (pre-emergence application) or after weeds emerge (post-emergence application), and are particularly effective when applied pre-emergence to the weeds.

Crops of useful plants in which the compositions according to the invention can be used include, but are not limited to, perennial crops, such as citrus fruit, grapevines, nuts, oil palms, olives, pome fruit, stone fruit and rubber, and annual arable crops, such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soy beans, sugar beet, sugar cane, sunflowers, ornamentals, switchgrass, turf and vegetables, especially cereals, maize and soy beans.

The grasses and weeds to be controlled may be both monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eriochloa, Lolium, Monochoria, Panicum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sida and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Euphorbia, Galium, lpomoea, Kochia, Nasturtium, Polygonum, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.

Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. auxins orALS-, EPSPS-, PPO-and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate-and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®, respectively.

Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle). Examples of Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds). The Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins, or transgenic plants able to synthesize such toxins, are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events). For example, seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.

Crops are also to be understood as being those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor).

The term "weeds" as used herein means any undesired plant, and thus includes not only agronomically important weeds as described above, but also volunteer crop plants.

The compounds of the present invention can be prepared, for example, by the processes detailed in EP 2336 104.

The compositions according to the invention are suitable for all the conventional methods of application in agriculture, such as, e.g., pre-emergent application, post-emergent application and seed dressing. Depending on the intended use, the safener can be employed for pre-treatment of the seed of the crop plant (dressing of the seed or cuttings) or can be introduced into the soil before or after sowing. However, it can also be applied by itself or together with the herbicide before or after emergence of the plants. The treatment of the plants or seed with the safener can therefore in principle be carried out independently of the time of application of the herbicide. Treatment of the plants by simultaneous application of the herbicide and safener (e.g, as a tank mix) is as a rule preferred. The application rate of safener to herbicide to be applied largely depends of the method of use. For field treatment, as a rule 0.001 to 5.0 kg of safener/ha, preferably 0.01 to 0.5 kg safener/ha and as a rule between 0.005 to 2 kg of herbicide/ha, but preferably between 0.01 to 1 kg/ha are applied. For seed dressing, in general 0.001 to lOg of safener/kg seed, preferably 0.05 to 2g safener/kg seed are applied.

If the safener is applied in liquid form, with soaking of the seed, shortly before sowing, safener solutions which contain the safener in a concentration of ito 10,000, preferably 100 to 1000 ppm are expediently used.The safened compositions) according to the invention can be used in unmodified form, as obtained in the synthesis, but they are generally formulated into herbicidal compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. Therefore, the invention also relates to a herbicidal composition which comprises a herbicidally effective amount of a compound of formula (I) and a safener in addition to formulation adjuvants.

The formulated compositions can be in various physical forms, e.g. in theform of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAQ Specifications for Plant Protection Products, 5th Edition, 1999. Such formulations can either be used directly or they are diluted prior to use. The dilutions can be made, for example, with water, liquid fertilizers, micronutrients, biological organisms, oil or solvents.

The formulated compositions can be prepared e.g. by mixing the active ingredient and safener combinationwith the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules consisting of a polymer Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art in this connection. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per so. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethyleneglycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, ni-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethyleneglycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, arnyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone and the like. Water is generally the carrier of choice for diluting the concentrates. Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances, as described, for example, in CFR 180.1001. (c)& (d).

A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use.

Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono-and di-alkylphosphate esters; and also further substances described e.g. in "McCutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981.

Further adjuvants that can usually be used in pesticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralizing or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and also liquid and solid fertilizers.

The formulated compositions according to the invention can additionally include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the spray mixture. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® (Rhâne-Poulenc Canada Inc.), alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. A preferred additive contains, for example, as active components essentially 80 % by weight alkyl esters of fish oils and 15% by weight methylated rapeseed oil, and also 5% by weight of customary emulsifiers and pH modifiers. Especially preferred oil additives comprise alkyl esters of CrC22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid, being of importance. Those esters are known as methyl laurate (CAS-111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9). A preferred fatty acid methyl ester derivative is Emery® 2230 and 2231 (Cognis GmbH). Those and other oil derivatives are also known from the Compendium of Herbicide Adjuvants, 5th Edition, Southern Illinois University, 2000.

The application and action of the oil additives can be further improved by combination with surface-active substances, such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed on pages 7 and 8 of WO 97/34485. Preferred surface-active substances are anionic surfactants of the dodecylbenzylsulfonate type, especially the calcium salts thereof, and also non-ionic surtactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C12-C22 fatty alcohols having a degree of ethoxylation of from 5 to 40.

Examples of commercially available surfactants are the Genapol types (ClariantAG). Also preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltriloxanes which are commercially available e.g. as Silwet L-77®, and also perfluorinated surfactants. The concentration of the surface-active substances in relation to the total additive is generally from ito 30 % by weight. Examples of oil additives consisting of mixtures of oil or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (Syngenta AG, CH) or ActipronC (BP Oil UK Limited, GB).

If desired, it is also possible for the mentioned surface-active substances to be used in the formulations on their own, that is to say, without oil additives.

Furthermore, the addition of an organic solvent to the oil additive/surfactant mixture may contribute to an additional enhancement of action. Suitable solvents are, for example, Solvesso® (ESSO) or Aromatic Solvent® (Exxon Corporation). The concentration of such solvents can be from 10 to 80 % by weight of the total weight. Oil additives that are present in admixture with solvents are described, for example, in US-A-4,834,908. A commercially available oil additive disclosed therein is known by the name MERGE® (BASF Corporation). A further oil additive that is preferred according to the invention is SCORE® (Syngenta Crop Protection Canada).

In addition to the oil additives listed above, for the purpose of enhancing the action of the compositions according to the invention it is also possible for formulations of alkylpyrrolidones (e.g. Agrimax®) to be added to the spray mixture. Formulations of synthetic lattices, e.g. polyacrylamide, polyvinyl compounds or poly-1-p-menthene (e.g. Bond®, Courier® or Emerald®) may also be used. It is also possible for solutions that contain propionic acid, for example Eurogkem Pen-e-trate®, to be added to the spray mixture as action-enhancing agent.

Formulated compositions of the invention generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of active compound mixture of the compound of formula (I) with a safener and from ito 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to % by weight of a surface-active substance. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The rates of application of the compound of formula (I) may vary within wide limits and depend on the nature of the soil, the method of application (pre-or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the grass or weed to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The compounds of formula (I) according to the invention are generally applied at a rate of from 10 to 2000 g/ha, especially from 50 to 1000 g/ha.

Various methods and techniques are suitable for using safeners or compositions containing them for protecting crop plants from the harmful actions of herbicides of formula (I), such as, for example, the following: i) Seed dressing a) Dressing of the seed with the safener formulated as a wettable powder by shaking in a vessel until uniform distribution over the seed surface is achieved (dry dressing).

About ito 500g of safener (4g to 2kg of wettable powder) per 100 kg of seed are used here.

b) Dressing of the seed with an emulsion concentrate of the safener by method a) (wet dressing).

c) Dressing by immersing the seed in a liquor with 100-1000 ppm of safener for ito 72 hours and optionally subsequent drying of the seed (immersion dressing).

The dressing of the seed or the treatment of the sprouted seed are of course the preferred methods of application, because the treatment with the safener is directed entirely at the target crop. As a rule, ito i000g of safener, preferably 5 to 250g of safener are used per 100 kg of seed, it being possible to deviate upwards or downwards from the limit concentrations stated (repeat dressing), depending on the methods, which also allows the addition of other active compounds or micronutrients.

U) Application as a tank mix A liquid processed mixture of safener and herbicide of formula (I) (reciprocal ratio of amounts between 101 and 1:100) is used, the application rate of herbicide being 0.005 to 5.0 kg per hectare. Such tank mixes are applied before or after sowing.

iii) Application into the seed furrow The safener is introduced into the open sown seed furrow as an emulsion concentrate, wettable powder or as granules. After the seed furrow has been covered, the herbicide is applied by the pre-emergent method in a conventional method.

iv) Controlled release of the safener The safener is absorbed in solution on to mineral carrier granules or polymerised granules (urea/formaldehyde) and dried. A coating which allows the safener to be released over a certain period of time can optionally be applied (coated granules).

Preferred formulations have especially the following compositions (% = percent by weight; active compound mixture means the mixture of a compound of formula I with a safener):).

Emulsifiable concentrates: active compound mixture: ito 95 %, preferably 60 to 90 % surface-active agent: ito 30 %, preferably 5 to 20 % liquid carrier: ito 80 %, preferably ito 35 % Dusts: active compound mixture: 0.i to iO %, preferably 0.i to 5% solid carrier: 99.9 to 90 %, preferably 99.9 to 99 % Suspension concentrates: active compound mixture: 5 to 75 %, preferably iO to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: ito 40 %, preferably 2 to 30 %

Wettable powders:

active compound mixture: 0.5 to 90 %, preferably ito 80 % surface-active agent: 0.5 to 20 %, preferably Ito iS % solid carrier: 5 to 95 %, preferably 15 to 90 % Granules: active compound mixture: 0.i to 30 %, preferably 0.1 to 15% solid carrier: 99.5 to 70 %, preferably 97 to 85 % The following Examples further illustrate, but do not limit, the invention.

Formulation Examples for herbicides of formula (l)(% = % by weight) Fl. Emulsifiable concentrates a) b) c) d) active compound mixture 5 % iO % 25 % 50 % calcium dodecylbenzenesulfonate 6 % 8 % 6 % 8 % castor oil polyglycol ether 4 % -4 % 4 % (36 mol of ethylene oxide) octyiphenol polyglycol ether -4 % -2 % (7-8 mol of ethylene oxide) NMP --10% 20% arom. hydrocarbon mixture 85 % 78 % 55 % 16 % C9-C12 Emulsions of any desired concentration can be obtained from such concentrates by dilution with water.

F2. Solutions a) b) c) d) active compound mixture 5 % 10 % 50 % 90 % 1 -methoxy-3-(3-methoxy- propoxy)-propane -20 % 20% - polyethylene glycol MW 400 20 % 10 % --NMP --30% 10% arom. hydrocarbon mixture 75 % 60 % --C9-c12 The solutions are suitable for use in the form of microdrops.

F3. Wettable powders a) b) c) d) active compound mixture 5 % 25 % 50 % 80 % sodium lignosulfonate 4 % -3 % -sodium lauryl sulfate 2 % 3 % -4 % sodium diisobutylnaphthalene-sulfonate -6% 5% 6% octylphenol polyglycol ether -1 % 2 % - (7-8 mol of ethylene oxide) highly dispersed silicic acid 1 % 3 % 5 % 10 % kaolin 88% 62% 35% -The active compound mixture is mixed thoroughly with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.

F4. Coated granules a) b) c) active compound mixture 0.1 % 5 % 15 % highly dispersed silicic acid 0.9 % 2 % 2 % inorganic carrier 99.0 % 93 % 83 % (diameter 0.1 -1 mm) e.g. CaCQ3 or Si02 The active compound mixture is dissolved in methylene chloride and applied to the carrier by spraying, and the solvent is then evaporated off in vacuo.

F5. Coated granules a) b) c) active compound mixture 0.1 % 5 % 15 % polyethylene glycol MW 200 1.0 % 2 % 3 % highly dispersed silicic acid 0.9 % 1 % 2 % inorganic carrier 98.0 % 92 % 80 % (diameter 0.1 -1 mm) e.g. CaCO3 or Si02 The finely ground active compound mixture is uniformly applied, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

F6. Extruder granules a) b) c) d) active compound mixture 0.1 % 3 % 5% 15% sodium lignosulfonate 1.5% 2 % 3 % 4 % carboxymethylcellulose 1.4 % 2 % 2 % 2 % kaolin 97.0% 93% 90% 79% The active compound mixture is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

F7. Dusts a) b) c) active compound mixture 0.1 % 1 % 5 % talcum 39.9 % 49 % 35 % kaolin 60.0% 50 % 60% Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.

F8. Suspension concentrates a) b) c) d) active compound mixture 3 % 10 % 25 % 50 % ethyleneglycol 5% 5% 5% 5% nonylphenol polyglycol ether -1 % 2 % - (15 mol of ethylene oxide) sodium lignosulfonate 3 % 3 % 4 % 5 % carboxymethylcellulose 1 % 1 % 1 % 1 % 37 % aqueous formaldehyde 0.2 % 0.2 % 0.2 % 0.2 % solution silicone oil emulsion 0.8 % 0.8 % 0.8 % 0.8 % water 87% 79% 62% 38% The finely ground active compound mixture is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

It is often more practical to formulate the active compound of formula I and the safener individually and then to bring them together as a tank mix' in water in the application equipment in the desired mixing ratio shortly before application.

The mixtures of the compound of formula (I) and a safener according to the invention can also be used in combination with further active ingredients, e.g. further herbicides and/or insecticides and/or acaricides and/or nematocides and/or molluscicides and/or fungicides and/or plant growth regulators.

Such mixtures, and the use of such mixtures to control weeds and/or undesired plant growth, form yet further aspects of the invention. For the avoidance of doubt, mixtures of invention also include mixtures of two or more different compounds of formula (I).

For the avoidance of doubt, where a literary reference, patent application, or patent, is cited within the text of this application, the entire text of said citation is herein incorporated by reference.

Claims

CLAIMS1. A composition comprising a haloalkylsulfonanilide derivative represented by the formula (1) or an agrochemically acceptable salt thereof: wherein A is -C(R7)(R8)-or -N(R9)-, W is an oxygen atom or a sulfur atom, n is an integer of from 1 to 4, R1 is halo C1 -C alkyl, R2 is a hydrogen atom, C1 -C6 alkyl, halo C1 -C6 alkyl, C2 -C alkenyl, halo 02 C alkenyl, C2 -Ce alkynyl, halo 02-06 alkynyl, 01-06 alkoxy 0106 alkyl, halo Ci C alkoxy 010e alkyl, -C alkoxy C Ce alkoxy 0 -C6 alkyl, tn C -C3 alkylsilyl C -C alkoxy C 0e alkyl, phenyl £6 alkyl, substituted phenyl Ci Ce alkyl having at least one substituent selected from Y, C - 2 alkylcarbonyl, halo C1C12 alkylcarbonyl, cyclo C3 alkylcarbonyl, cyclo C3 C alkyl 01 £6 alkylcarbonyl, 020 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y, heterocyclic carbonyl, substituted heterocyclic carbonyl having at least one substituent selected from Y, C -C1 2 alkoxycarbonyl, halo C -C 2 alkoxycarbonyl, C C alkoxy C £ alkoxycarbonyl, 0 -C6 alkylthio C1 -C6 alkoxycarbonyl, 0 £6 alkylsulfinyl Cl -C alkoxycarbonyl, C1 -C6 alkylsulfonyl C1 -C alkoxycarbonyl, C2 -C6 alkenyloxycarbonyl, halo 02 -06 alkenyloxycarbonyl, 02 -06 alkynyloxycarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl having at least one substituent selected from Y, phenyl C1 -C6 alkoxycarbonyl, substituted phenyl C -0 alkoxycarbonyl having at least one substituent selected from Y, phenoxy C alkylcarbonyl, substituted phenoxy 0 Ce alkylcarbonyl having at least one substituent selected from Y, mono(C1 -C alkyl)aminocarbonyl, mono(halo 0 £ alkyl)aminocarbonyl, symmetric or asymmetric di(C1 £6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1 -C3 alkyl)aminocarbonyl, 01 -C alkylthiocarbonyl, halo C1 -C alkylthiocarbonyl, C1 -C alkylsulfonyl, halo C £6 alkylsulfonyl, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y, C 0 alkylthio C1 -C3 alkyl, halo -06 alkylthio C -06 alkyl, phenyl C -06 alkoxy 01-06 alkyl, substituted phenyl C -06 alkoxy C £3 alkyl having at least one substituent selected from Y, phenylthio C1 -C6 alkyl, substituted phenylthio C 0 alkyl having at least one substituent selected from Y, phenyl 01 -06 alkylthio 01 -06 alkyl, substituted phenyl C -06 alkylthio 0 0 alkyl having at least one substituent selected from Y, phenylsulfonyl 01 -06 alkyl, substituted phenylsulfonyl C -06 alkyl having at least one substituent selected from 1, phenyl Oi-O alkylsulfonyl Ci C alkyl, substituted phenyl C C alkylsulfonyl C -C alkyl having at least one substituent selected from 1, C -06 alkylcarbonyloxy Ci Ce alkyl, phenylcarbonyloxy C £ alkyl, substituted phenylcarbonyloxy C £6 alkyl having at least one substituent selected from Y, phenylcarbonyl C -C6 alkyl, substituted phenylcarbonyl C -06 alkyl having at least one substituent selected from Y, C C6 alkoxycarbonyloxy C1 -C6 alkyl, phenylcarbonyloxy C -C6 alkoxy C -C6 alkyl, substituted phenylcarbonyloxy C1 -C6 alkoxy C -C6 alkyl having at least one substituent selected from Y, mono C £6 alkylaminocarbonyloxy Ci -06 alkyl, symmetric or asymmetric di(01 £6 alkyl)aminocarbonyloxy 01 -C6 alkyl, phenylaminocarbonyloxy C -C6 alkyl, substituted phenylaminocarbonyloxy C £e alkyl having at least one substituent selected from Y, Ci -06 alkyl(phenyl)aminocarbonyloxy C £ alkyl, substituted 01 -C6 alkyl(phenyl)aminocarbonyloxy C £6 alkyl having at least one substituent selected from Y, C1 £6 alkylcarbonyl 01C6 alkyl, £ alkoxycarbonyl C1 -C6 alkyl, halo C1 -C alkylthio, symmetric or asymmetric di(C1 -C6 alkyl)aminothio or cyano, each of R3 and R4 is independently a hydrogen atom, C1 £6 alkyl, halo C £6 alkyl, cyclo C3 C alkyl, halocyclo C3 C alkyl, C -C6 alkoxy, halo C1 £ alkoxy, halogen or cyano, or R3 and R4 may form a 3-to 7-membered ring together with each other, each of R5, R6, R7 and R6 is independently a hydrogen atom, a halogen, C C alkyl, halo C £6 Ikyl, 0206 alkenyl, 0206 alkynyl, cyclo 03-06 alkyl, halocyclo 03-06 alkyl, C £ alkoxy £6 alkyl, halo C106 alkoxy 0106 alkyl, hydroxy 0106 alkyl, C106 alkylthio CC alkyl, halo C £6 alkylthio C -06 alkyl, mono(C1 £6 alkyl)amino C -06 alkyl, symmetric or asymmetric di(C1 £5 alkyl)amino C £6 alkyl, phenyl, substituted phenyl having at least one substituent selected from Y, heterocyclyl, substituted heterocyclyl having at least one substituent selected from Y, phenyl C alkyl, substituted phenyl C -C6 alkyl having at least one substituent selected from Y, phenoxy C1 C alkyl, substituted phenoxy Ci £ alkyl having at least one substituent selected from Y, C alkylcarbonyl, halo C1 -C6 alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y, C -C6 alkoxycarbonyl, halo C1 -C6 alkoxycarbonyl, carboxyl, mono(C1 £ alkyl)aminocarbonyl, symmetric or asymmetric di(C1 £6 alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from Von the ring, phenyl Ci £ alkylaminocarbonyl, substituted phenyl C alkylaminocarbonyl having at least one substituent selected from Von the ring, C -C alkoxy, halo C £ alkoxy, phenoxy, substituted phenoxy having at least one substituent selected from Y on the ring, C1 £ alkylthio, halo C -C6 alkylthio, phenylthio, substituted phenylthio having at least one substituent selected from Von the ring, C1 C6 alkylsulfonyl, halo C1C6 alkylsulfonyl, mono(C1 £ alkyamino, di(C1 C6 alkyl)amino, C £6 alkylcarbonyloxy, hydroxy, amino, cyano or nitro, R9 is a hydrogen atom, Ci Ce alkyl, halo Ci £6 alkyl, cyclo 03-Ce alkyl, halocyclo 03-Ce alkyl, C2 -06 alkenyl, halo 02-06 alkenyl, 02-06 alkynyl, C1 -0 alkoxy 01-06 alkyl, halo C -C alkoxy 01 -06 alkyl, hydroxy 0 0 alkyl, cyclo C -C alkyl 0 0 alkyl, phenyl 0i -06 alkyl, substituted phenyl C1 -06 alkyl having at least one substituent selected from Y on the ring, phenyl, substituted phenyl having at least one substituent selected from Y on the ring, phenoxy C Ce alkyl, substituted phenoxy C -C alkyl having at least one substituent selected from Y on the ring, -06 alkylcarbonyl 01 -06 alkyl, halo C £e alkylcarbonyl Ci Ce alkyl, 0 Ce alkoxycarbonyl C1 £6 alkyl, halo C1 £ alkoxycarbonyl C -C6 alkyl, C1 alkylcarbonyl, halo 0 -C6 alkylcarbonyl, cyclo 03-06 alkylcarbonyl, cyclo 03-06 alkyl Ci C alkylcarbonyl, 02-06 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y on the ring, heterocyclic carbonyl, substituted heterocyclic carbonyl having at least one substituent selected from 1, 0 -06 alkoxycarbonyl, halo 0 Le alkoxycarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl having at least one substituent selected from Y, aminocarbonyl, mono(01 Le alkyl)aminocarbonyl, monohalo(C1 -06 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 £ alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1 alkyl)aminocarbonyl, C £6 alkylthiocarbonyl, halo alkylthiocarbonyl, CiC6 alkylsulfonyl, halo C1 alkylsulfonyl, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y, C -C alkylthio C -06 alkyl, halo C -06 alkylthio C -06 alkyl, phenylthio C1 -C alkyl, substituted phenylthio C1 -C alkyl having at least one substituent selected from Y, 01-06 alkylsulfinyl C1 -C alkyl, halo C -C alkylsulfinyl 01-06 alkyl, phenylsulfinyl C -06 alkyl, substituted phenylsulfinyl C £6 alkyl having at least one substituent selected from Y, C -06 alkylsulfonyl C -06 alkyl, halo C1 £6 alkylsulfonyl C -0e alkyl, phenylsulfonyl C -Ce alkyl, substituted phenylsulfonyl C -06 alkyl having at least one substituent selected from Y, cyano, amino or hydroxy, or R5, R6, R7 or R6 may form, together with R5, R6, R7 or R3 on the same carbon, an optionally substituted 3-to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with C -C alkyl, 02-06 alkenyl, C2C6 alkynyl or cyclo 03-Ce alkyl), an olefin or carbonyl, or R5, R6, R7 or R8 may form, together with R5, R6, R7 or on a different carbon, an optionally substituted 3-to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with 0 - 0e alkyl, C2 C alkenyl, C2 C alkynyl or cyclo C3 -C6 alkyl), or R5 or R6 may form a bond together with R5 or R6 on an adjacent carbon, when n is from 2 to 4, R5 or R6 may be the same as or different from R5 or R6 on an adjacent carbon, Xis halogen, 01-06 alkyl, 02-Ce alkenyl, 02-06 alkynyl, cyclo 03-06 alkyl, halo 01-06 alkyl, halocyclo C3 C alkyl, C -C alkoxy, halo C -0e alkoxy, C -0e alkylthio, halo C -0e alkylthio, 0 C alkylsulfinyl, halo C alkylsulfinyl, C1 £ alkylsulfonyl, halo C -C alkylsulfonyl, phenyl, substituted phenyl having at least one substituent selected from Y on the ring, heterocyclyl, substituted heterocyclyl having at least one substituent selected from Y on the ring, phenoxy, substituted phenoxy having at least one substituent selected from Y on the ring, phenylthio, substituted phenylthio having at least one substituent selected from Von the ring, phenylsulfinyl, substituted phenylsulfinyl having at least one substituent selected from Von the ring, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y on the ring, 01 0 alkylcarbonyl, halo Ci C alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Von the ring, C -C alkoxycarbonyl, halo C -06 alkoxycarbonyl, carboxyl, mono(Ci C alkyl)aminocarbonyl, monohalo(Ci Ce alkyl)aminocarbonyl, symmetric or asymmetric di(01 £6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1 -C alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from Von the ring, phenyl 0 C alkylaminocarbonyl, substituted pheny lC £6 alkylaminocarbonyl having at least one substituent selected from Von the ring, hydroxy, amino, cyano or nitro, Visa halogen, 0 alkyl, 0206 alkenyl, 0206 alkynyl, cyclo 03-06 alkyl, halo 0106 alkyl, halocyclo 03-0 alkyl, C £ alkoxy, halo 0106 alkoxy, alkylthio, halo C -06 alkylthio, 01 -06 alkylsulfinyl, halo C C alkylsulfinyl, C C alkylsulfonyl, halo C -06 alkylsulfonyl, phenyl, substituted phenyl having at least one substituent selected from the group consisting of halogen, 0 £e alkyl, 0206 alkenyl, 0206 alkynyl, cyclo C -Ce alkyl, halo C - C alkyl, halocyclo 0 C alkyl, 0 0 alkoxy, halo C £ alkoxy, C -C alkylthio, halo C -C alkylthio, Ci C alkylsulfinyl, halo C -C alkylsulfinyl, Ci Ce alkylsulfonyl, halo C £6 alkylsulfonyl, C 0 alkylcarbonyl, halo C 0 alkylcarbonyl, C 0 alkoxycarbonyl, carboxyl, mono(01 £6 alkyl)aminocarbonyl, symmetric or asymmetric di(01 £6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, heterocyclyl, substituted heterocyclyl having at least one substituent selected from the group consisting of halogen, C 0 alkyl, 02 06 alkenyl, C2 alkynyl, cyclo 03-Ce alkyl, halo alkyl, halocyclo 03-06 alkyl, CCe alkoxy, halo 0106 alkoxy, C 0 alkylthio, halo C C alkylthio, C 0 alkylsulfinyl, halo C C alkylsulfinyl, C - C alkylsulfonyl, halo C £6 alkylsulfonyl, Ci Ce alkylcarbonyl, halo Ci -Ce alkylcarbonyl, C - Ce alkoxycarbonyl, carboxyl, mono(C1 C alkyl)aminocarbonyl, symmetric or asymmetric di(01 -Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenoxy, substituted phenoxy having at least one substituent selected from the group consisting of halogen, C £ alkyl, 02 C alkenyl, C2 £6 alkynyl, cyclo 03-06 alkyl, halo 0 0 alkyl, halocyclo 03-0 alkyl, 0 0 alkoxy, halo C £ alkoxy, C £ alkylthio, halo 01 £ alkylthio, 06 alkylsulfinyl, halo C £ alkylsulfinyl, 01 £6 alkylsulfonyl, halo C £6 alkylsulfonyl, 01 -06 alkylcarbonyl, halo Ci -Ce alkylcarbonyl, C C alkoxycarbonyl, carboxyl, mono(C1 £6 alkyl)aminocarbonyl, symmetric or asymmetric di(01 £ alkyaminocarbonyl, hydroxyl, amino, cyano and nitro, phenylthio, substituted phenylthio having at least one substituent selected from the group consisting of halogen, 01 0 alkyl, 02 06 alkenyl, C2 0 alkynyl, cyclo C 0 alkyl, halo C Ce alkyl, halocyclo 03-0 alkyl, C £ alkoxy, halo C106 alkoxy, 0106 alkylthio, halo 01 -06 alkylthio, C106 alkylsulfinyl, halo C £ alkylsulfinyl, 0106 alkylsulfonyl, halo C £6 alkylsulfonyl, C C alkylcarbonyl, halo Ci C alkylcarbonyl, C £ alkoxycarbonyl, carboxyl, mono(01 £ alkyl)aminocarbonyl, symmetric or asymmetric di(C1 £ alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfinyl, substituted phenylsulfinyl having at least one substituent selected from the group consisting of halogen, C Le alkyl, C2C6 alkenyl, 0206 alkynyl, cyclo C3 -C6 alkyl, halo 01-06 alkyl, halocyclo C3 -06 alkyl, C1 -C6 alkoxy, halo 01-06 alkoxy, C -C alkylthio, halo C -06 alkylthio, C C alkylsulfinyl, halo oi -06 alkylsulfinyl, C - C6 alkylsulfonyl, halo C -06 alkylsulfonyl, C C alkylcarbonyl, halo C1 -C alkylcarbonyl, C - Ce alkoxycarbonyl, carboxyl, mono(C1 -Ce alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from the group consisting of halogen, C -C alkyl, C2C6 alkenyl, C2C6 alkynyl, cyclo C3C6 alkyl, halo alkyl, halocyclo C3C6 alkyl, C -06 alkoxy, halo C -Ce alkoxy, Ci -Ce alkylthio, halo Ci -Ce alkylthio, 0i -Ce alkylsulfinyl, halo C alkylsulfinyl, C1 alkylsulfonyl, halo C -C alkylsulfonyl, C C alkylcarbonyl, halo C alkylcarbonyl, C1C6 alkoxycarbonyl, carboxyl, mono(C1 C6 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, C1 -C6 alkylcarbonyl, halo C1 -C6 alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from the group consisting of halogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 £6 alkynyl, cycloC3 -C6 alkyl, halo C1 co alkyl, halocyclo C3 - C6 alkyl, 01-06 alkoxy, halo 01-06 alkoxy, C1-C alkylthio, halo 01-06 alkylthio, Ci - C6 alkylsulfinyl, halo C1 -C6 alkylsulfinyl, C -C6 alkylsulfonyl, halo C1 -C6 alkylsulfonyl, C1 -C6 alkylcarbonyl, halo C -06 alkylcarbonyl, C -ce alkoxycarbonyl, carboxyl, mono(C1 -C6 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 C alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, Cl -C alkoxycarbonyl, carboxyl, mono(C1 -06 alkyaminocarbonyl, symmetric or asymmetric di(C1 -06 alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from the group consisting of halogen, 01-06 alkyl, 02-06 alkenyl, 02-Ce alkynyl, cyclo 03-Ce alkyl, halo C -C alkyl, halocyclo C3 C alkyl, C -C alkoxy, halo C £6 alkoxy, C C alkylthio, halo Cl £6 alkylthio, 01-06 alkylsulfinyl, halo C -C alkylsulfinyl, C -C alkylsulfonyl, halo C -06 alkylsulfonyl, C -C alkylcarbonyl, halo C -06 alkylcarbonyl, C -0 alkoxycarbonyl, carboxyl, mono(C1 -06 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -06 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenyl C1 -C6 alkylaminocarbonyl, substituted phenyl C -alkylaminocarbonyl having at least one substituent selected from the group consisting of halogen, C -C6 alkyl, 02-Ce alkenyl, 02-06 alkynyl, cyclo C3C6 alkyl, halo Cl_Ce alkyl, halocyclo 03 C6 alkyl, C -06 alkoxy, halo C 0e alkoxy, C -06 alkylthio, halo C -0e alkylthio, C -0e alkylsulfinyl, halo C1 Ce alkylsulfinyl, C1 Ce alkylsulfonyl, halo C Ce alkylsulfonyl, C C6 alkylcarbonyl, halo Cl_Co alkylcarbonyl, Cl_Co alkoxycarbonyl, carboxyl, mono(C1 C alkyl)aminocarbonyl, symmetric or asymmetric di(C1 Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, hydroxy, amino, cyano or nitro, or Y may be C 04 alkylene, halo C1 C4 alkylene, C2 C4 alkenylene or halo C2C4 alkenylene which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with C1 -C6 alkyl, C2C6 alkenyl, C2C6 alkynyl or cyclo C3 -C6 alkyl) and form a 5-or 6-membered ring together with an adjacent carbon or nitrogen atom on a benzene ring or a heterocyclyl, and the heterocyclyl is thienyl, furyl. pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, I,2,4-triazinyl, benzothienyl, benzofuryl, indolyl, benzothiazolyl, benzoimidazolyl, benzoisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl, provided that in a group having two or more substituents, the substituents may be the same or different, and wherein said composition comprises, in addition to the herbicide, at least one safener selected from the group consisting of AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxad ifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, Tl-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (GAS RN 221668-34- 4) and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)ani ino]benzenesu Ifonamide.
2. The compositon of claim 1, wherein n is 1 or 4.
3. The composition of claim 1, wherein n is 2 or 3 and at least one of R5 and R6 is not H, Oi5alkyl, GlAhaloalkyl, G36cycloalkyl, G14alkoxyC14alkyl, phenyl or substituted phenyl.
4. The composition of any one of the preceding claims, wherein W is S.
5. The composition of any one of the preceding claims, wherein X is 02.06 alkyl, 02.06 alkenyl, 02.06 alkynyl, cyclo 03.06 alkyl, halo G.G alkyl, halocyclo 03.06 alkyl, G.G alkoxy, halo C.06 alkoxy, C.C alkylthio, halo C -C alkylthio, C.G alkylsulfinyl, halo C -alkylsulfinyl, C -C alkylsulfonyl, halo Cl -C6 alkylsulfonyl, phenyl, substituted phenyl having at least one substituent selected from Y on the ring, heterocyclyl, substituted heterocyclyl having at least one substituent selected from Y on the ring, phenoxy, substituted phenoxy having at least one substituent selected from Y on the ring, phenylthio, substituted phenylthio having at least one substituent selected from Y on the ring, phenylsulfinyl, substituted phenylsulfinyl having at least one substituent selected from Y on the ring, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y on the ring, C -C alkylcarbonyl, halo G £ alkylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Y on the ring, C C alkoxycarbonyl, halo 01 -G alkoxycarbonyl, carboxyl, mono(C1 -alkyl)aminocarbonyl, monohalo(G1 £ alkyl)aminocarbonyl, symmetric or asymmetric di(C1 £ alkyl)aminocarbonyl, symmetric or asymmetric halo di(01 -G alkyl)aminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl having at least one substituent selected from Y on the ring, phenyl Cl -G alkylaminocarbonyl, substituted pheny lC -C alkylaminocarbonyl having at least one substituent selected from Y on the ring, hydroxy, amino, cyano or nitro.
6. The composition of any one of the preceding claims, wherein R1 is not trifluoromethyl.
7. The composition of any one of the preceding claims, wherein R2 is Ge-Ce alkyl, halo 01-06 alkyl, halo G2Ge alkenyl, C4-Ge alkynyl, halo G2Ge alkynyl, G-C alkoxy G1C6 alkyl, C1-C4alkoxyC3-C6alkyl, halo Cl-Ce alkoxy C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, tn 01-Go alkylsilyl Cl-Ce alkoxy C1C6 alkyl, 06-012 alkylcarbonyl, halo C5C12 alkylcarbonyl, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, halo C5-C12 alkoxycarbonyl, C1-Ce alkylthio Cl-Ce alkoxycarbonyl, C1-C alkylsulfinyl C-C alkoxycarbonyl, C-C alkylsulfonyl C1-Ce alkoxycarbonyl, halo CrC8 alkenyloxycarbonyl, phenoxy C1-C6 alkylcarbonyl, phenoxy C1-C6 alkylcarbonyl substituted with at least one Y, mono(halo C1-C6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C1-C6 alkyl)aminocarbonyl, halo C1-C6 alkylthiocarbonyl, 05-Ce alkylsulfonyl, halo 05-C6 alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, halo C1C6 alkylthio C1-C6 alkyl, phenyl C1-C6 alkylthio C-C alkyl, phenyl C1-C6 alkylthio C1-C6 alkyl substituted with at least one Y, phenylsulfonyl C1-C6 alkyl, phenylsulfonyl C1-C6 alkyl substituted with at least one Y, phenyl C1-C6 alkylsulfonyl C1-C6 alkyl, phenyl C1-C6 alkylsulfonyl C1-C6 alkyl substituted with at least one Y, C1-C6 alkylcarbonyloxy Ci-C6 alkyl, phenylcarbonyloxy Ci-C6 alkyl, phenylcarbonyloxy C1-C6 alkyl substituted with at least one Y, phenylcarbonyl ClC6 alkyl, phenylcarbonyl C1-C6 alkyl substituted with at least one Y, Cl-Ce alkoxycarbonyloxy C1-C6 alkyl, phenylcarbonyloxy Cl-ce alkoxy C1-06 alkyl, phenylcarbonyloxy C1-C6 alkoxy C1-C6 alkyl substituted with at least one Y, mono 0l0e alkylaminocarbonyloxy C-C alkyl, symmetric or asymmetric di(C1-C6 alkyl)aminocarbonyloxy C1-06 alkyl, phenylaminocarbonyloxy C1-C alkyl, phenylaminocarbonyloxy Cl-Ce alkyl substituted with at least one Y, Cl-Ce alkyl(phenyaminocarbonyloxy C1-C al kyl, C1-C alkyl(phenyl)am i nocarbonyloxy 0-0e alkyl substituted with at least one Y, ClCe alkylcarbonyl Cl-Ce alkyl, Cl-Ce alkoxycarbonyl Cl-Ce alkyl, halo C1-Ce alkylthio, symmetric or asymmetric di(C1-C6 alkyl)aminothio or cyano.
8. The composition of any one of the preceding claims, wherein each of R3 and R4 is, independently, a hydrogen atom, 01.06 alkyl, halo 01 C6 alkyl, cyclo 03. C6 alkyl, halocyclo 03.06 alkyl, C1 -C6 alkoxy, halo C1 -C6 alkoxy, halogen or cyano, or R3 and R.4 may form a 3-to 7-membered ring together with each other, with the proviso that at least one of R3 and R4 is other than a hydrogen atom.
9. The composition of any one of the preceding claims, wherein A is -C(R4(R5)-and at least one of R7 and R9 is not H, halogen, C1.4alkyl, Ci.4alkoxy, Ci.4alkylthio or C1.4alkoxycarbonyl.
10. The composition of any one of claims ito 8, wherein A is -N(R9)-and R9 is C5 Ce alkyl, halo Cl - 0e alkyl, cyclo 03-C alkyl, halocyclo C3 -Ce alkyl, C2 -C alkenyl, halo C2 -Ce alkenyl, 02 0e alkynyl, Cl -0e alkoxy Cl -ce alkyl, halo Cl -Ce alkoxy Cl -0e alkyl, hydroxy Cl -C alkyl, cyclo 03-C6 alkyl C -06 alkyl, phenyl C1 -C5 alkyl, substituted phenyl C1 -C5 alkyl having at least one substituent selected from Y on the ring, phenoxy Cl -C6 alkyl, substituted phenoxy Cl -C6 alkyl having at least one substituent selected from Y on the ring, C1 -0e alkylcarbonyl Cl -Ce alkyl, halo C1 -Ce alkylcarbonyl Cl -0e alkyl, Cl -C alkoxycarbonyl C1 -0e alkyl, halo C -0e alkoxycarbonyl C -C alkyl, C alkylcarbonyl, halo C1 -0e alkylcarbonyl, cyclo 03-Cc alkylcarbonyl, cyclo C3 -C5 alkyl Cl -06 alkylcarbonyl, C2 -06 alkenylcarbonyl, phenylcarbonyl, substituted phenylcarbonyl having at least one substituent selected from Von the ring, heterocyclic carbonyl, substituted heterocyclic carbonyl having at least one substituent selected from Y, 05.06 alkoxycarbonyl, halo C1. C6 alkoxycarbonyl, phenoxycarbonyl, substituted phenoxycarbonyl having at least one substituent selected from 1, aminocarbonyl, mono(Ci -C6 alkyl)aminocarbonyl, monohalo(C1 -06 alkyl)aminocarbonyl, symmetric or asymmetric di(C1 -06 alkyl)aminocarbonyl, symmetric or asymmetric halo di(01 £ alkyaminocarbonyl, C -06 alkyithiocarbonyl, halo C1 -C6 alkylthiocarbonyl, C -0 alkylsulfonyl, halo C -06 alkylsulfonyl, phenylsulfonyl, substituted phenylsulfonyl having at least one substituent selected from Y, 0 -06 alkylthio 01 06 alkyl, halo 01 06 alkylthio C -C alkyl, phenylthio 01 06 alkyl, substituted phenylthio Ci 0 alkyl having at least one substituent selected from Y, C -C alkylsulfinyl 0 - 06 alkyl, halo C.C6alkylsulfinyl C1C6 alkyl, phenylsulfinyl C1C6 alkyl, substituted phenylsulfinyl C Le alkyl having at least one substituent selected from Y, 0 Le alkylsulfonyl C.C alkyl, halo C 06 alkylsulfonyl C £6 alkyl, phenylsulfonyl C1 -C6 alkyl, substituted phenylsulfonyl C alkyl having at least one substituent selected from Y, cyano, amino or hydroxyl.
11. A method for protecting crops of useful plants from the harmful effects of a herbicide of formula (I) as defined in any one of claims ito 10, which comprises applying to the locus of the useful plants at least one safener selected from the group consisting of AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, Tl-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (GAS RN 221 668-34-4) and N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide.
12. A method for combating weeds in crops of useful plants, which comprises treating the useful plants, seeds or cuttings thereof or the locus of the useful plants simultaneously or at separate times with a herbicidally active amount of a compound of formula (I) as defined in any one of claims ito 10 and at least one safener selected from the group consisting of AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, the corresponding (Z) isomer of cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, the corresponding R isomer of furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride, 11-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)- benzamide (GAS RN 221668-34-4) and N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide.