WO2013079672A1

WO2013079672A1 - Herbicidal uses of substituted spiroheterocyclic pyrrolidine dione derivatives, and herbicidal compositions comprising them

Info

Publication number: WO2013079672A1
Application number: PCT/EP2012/074118
Authority: WO
Inventors: Nicholas Ryan SMITH; Michel Muehlebach; Jürgen Harry SCHAETZER
Original assignee: Syngenta Limited; Syngenta Participations Ag
Priority date: 2011-11-30
Filing date: 2012-11-30
Publication date: 2013-06-06
Also published as: GB201120644D0

Abstract

The invention relates to a method of controlling weeds in crops of useful plants, which comprises applying a compound of the formula I or an agrochemically acceptable salt thereof: wherein (i) one or both of R² and R⁶ is or are, independently, C_2-3alkynyl; and/or (ii) R⁴ is C_2-4alkynyl; and wherein the substituents are otherwise as defined herein, or applying a herbicidal composition comprising such a compound or salt, to the weeds and/or to the plants and/or to the locus thereof. Preferably, the weeds to be controlled comprise grassy monocotyledonous weeds. The invention also relates to a herbicidal composition, for use in a method of controlling weeds in crops of useful plants, which composition comprises a compound of formula (I) as defined herein or an agrochemically acceptable salt thereof, and a substantially-inert agrochemically acceptable substance such as an agrochemically acceptable carrier, diluent and/or solvent therefor.

Description

Herbicidal uses of substituted spiroheterocyclic pyrrolidine dione derivatives, and herbicidal compositions comprising them

The present invention relates to the herbicidal uses of substituted spiroheterocyclic pyrrolidine dione derivatives, and to herbicidal compositions comprising them.

Spiroheterocyclic pyrrolidine dione derivatives are disclosed, for example as insecticides, in WO 2009/049851 , WO 2010/063670 and WO 2010/066780. WO 2010/052161 A2 (Syngenta Participations AG) discloses herbicidal compositions comprising certain alkoxy-substituted spiroheterocyclic pyrrolidine dione compounds, and the use of these compounds in controlling grasses and weeds in crops of useful plants.

It has now surprisingly been found that certain substituted spiroheterocyclic pyrrolidine dione compounds, having an alkynyl-phenyl- headgroup, have herbicidal properties.

The present invention therefore provides a method of controlling weeds in crops of useful plants, which comprises applying a compound of the formula (I) or an agrochemically acceptable salt thereof (e.g. a herbicidally effective amount of a compound of formula (I) or the salt thereof):

or applying a herbicidal composition comprising such a compound or salt (e.g. a

herbicidally effective amount thereof), to the weeds and/or to the plants and/or to the locus thereof; wherein:

R² is Ci_-3alkyl, C_2-3alkenyl, C_2-3alkynyl, cyclopropyl, Ci_-2fluoroalkyl, Ci_-2alkoxy,

Ci_-2fluoroalkoxy, or halogen; R⁴ is hydrogen, Ci_-4alkyl, C_2-4alkenyl, C_2-4alkynyl, C_3-6cycloalkyl, Ci_-2fluoroalkyl, Ci_-4alkoxy, Ci_-2fluoroalkoxy, halogen; or phenyl or phenyl substituted by 1 , 2 or 3 of, independently, Ci_-3alkyl, Ci_-2fluoroalkyl, Ci_-3alkoxy, Ci_-2fluoroalkoxy, halogen or cyano;

R⁵ is hydrogen or Ci_-2alkyl; or R⁵ is phenyl or phenyl substituted by 1 , 2 or 3 of,

independently, Ci_-3alkyl, Ci_-2fluoroalkyl, Ci_-3alkoxy, Ci_-2fluoroalkoxy, halogen or cyano; and R⁶ is hydrogen, Ci_-3alkyl, C_2-3alkenyl, C_2-3alkynyl, cyclopropyl, Ci_-2fluoroalkyl, Ci_-2alkoxy, Ci_-2fluoroalkoxy, or halogen; provided that:

(i) one or both of R² and R⁶ is or are, independently, C_2-3alkynyl; and/or

(ii) R⁴ is C_2-4alkynyl; and provided that one, two or all of of R⁴, R⁵ and R⁶ is or are not hydrogen;

and provided that when R⁴ is not hydrogen, then R⁵ is hydrogen or Ci_-2alkyl; and wherein:

A is either NR¹ or NOR¹ ;

wherein R¹ is hydrogen, Ci_-6alkyl, Ci_-4fluoroalkyl, C_3-6cycloalkyl, or C_3-6cycloalkyl wherein in the cycloalkyi moiety one methylene group is replaced by O, S or NR₀, where R₀ is Ci_-4alkyl or Ci_-4alkoxy;

or R¹ is C₃-₆cycloalkyl(Ci_-3)alkyl-, or C₃-₆cycloalkyl(Ci_-3)alkyl- wherein in the cycloalkyi moiety one methylene group is replaced by O, S or NR₀, where R₀ is Ci_-4alkyl or Ci_-4alkoxy; or R¹ is C_2-4alkenyl-CH₂-, C_2-4alkenyl-CH(Me)-, C_2-3fluoroalkenyl-CH₂-,

C₂chloroalkenyl-CH₂-, C_2-4alkynyl-CH₂-, Ci_-4cyanoalkyl, benzyl, furanyl(Ci_-2)alkyl-,

Ci-₄alkoxy(Ci_-4)alkyl, Ci-₃alkoxy(Ci_-3)alkoxy(Ci_-3)alkyl, Ci_-4alkylthio(Ci_-4)alkyl,

Ci-₄alkylsulfinyl(Ci_-4)alkyl or Ci_-4alkylsulfonyl(Ci_-4)alkyl; provided that, when both R⁴ and R⁶ are hydrogen, then A is NR¹ and R¹ is hydrogen;

R is hydrogen, Ci_-6alkyl, Ci_-4fluoroalkyl, Ci_-4cyanoalkyl, C_2-4alkenyl-CH₂-,

C_2-4alkenyl-CH(Me)-, C_2-3fluoroalkenyl-CH₂-, C_2-3chloroalkenyl-CH₂-, C₂-C₄alkynyl-CH₂-, benzyl, Ci_-4alkoxy(Ci_-4)alkyl, or Ci-₃alkoxy(Ci_-3)alkoxy(Ci_-3)alkyl; and

G is hydrogen, a metal, ammonium, sulfonium or a latentiating group; and wherein, when G is a latentiating group then G is CrC₈alkyl, C₂-C₈fluoroalkyl, phenylCrC₈alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of,

independently, d-C₃alkyl, CrC₃fluoroalkyl, CrC₃alkoxy, CrC₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, CrC₃alkylsulfonyl, halogen, cyano or by nitro), heteroarylCi-C₈alkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, Ci-C₃ alkylsulfonyl, halogen, cyano or by nitro), C₃-C₈alkenyl, C₃-C₈fluoroalkenyl, C₃-C₈alkynyl, -C(X^a)-R^a, -C(X^b)-X^c-R^b, -C(X^d)-N(R^c)-R^d, -S0₂-R^e, -P(X^e)(R )-R⁹ or -CH₂-X-R^h; wherein X^a, X^b, X^c, X^d, X^e and X are independently of each other oxygen or sulfur; and wherein:

R^a is H, Ci-Ci₈alkyl, C₂-Ci₈alkenyl, C₂-Ci₈alkynyl, Ci-Ciofluoroalkyl, CrCi₀cyanoalkyl, d- Ci₀nitroalkyl, Ci-Ci₀aminoalkyl, Ci-C₅alkylaminoCi-C₅alkyl, C₂-C₈dialkylaminoCi-C₅alkyl, C₃- C₇cycloalkylCi-C₅alkyl, Ci-C₅alkoxyCi-C₅alkyl, C₃-C₅alkenyloxyCi-C₅alkyl, C₃- C₅alkynyloxyCi-C₅alkyl, Ci-C₅alkylthioCi-C₅alkyl, Ci-C₅alkylsulfinylCi-C₅alkyl, C

C₅alkylsulfonylCi-C₅alkyl, C₂-C₈alkylideneaminoxyCi-C₅alkyl, Ci-C₅alkylcarbonylCi-C₅alkyl, Ci-C₅alkoxycarbonylCi-C₅alkyl, aminocarbonylCi-C₅alkyl, d-dalkylaminocarbonyld- C₅alkyl, C₂-C₈dialkylaminocarbonylCi-C₅alkyl, Ci-C₅alkylcarbonylaminoCi-C₅alkyl, /V-d- C₅alkylcarbonyl-/V-Ci-C₅alkylaminoCi-C₅alkyl, C₃-C₆trialkylsilylCi-C₅alkyl, phenylC C₅alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, d- dfluoroalkyl, d-C₃alkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-C₃fluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1 , 2 or 3 of,

independently, d-d alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;

R^b is Ci-Ci₈alkyl, d-dsalkenyl [e.g. C₂-d₇alkenyl-CH₂- or d-Ci₆alkenyl-CH(Me)-], d- Ci₈alkynyl [e.g. C₂-d₇alkynyl-CH₂- or d-Ci₆alkynyl-CH(Me)-], d-Ci₀fluoroalkyl, d- Ciocyanoalkyl, Ci-Ci₀nitroalkyl, d-Ci₀aminoalkyl, d-dalkylaminod-dalkyl, C₂- ddialkylaminoCrdalkyl, d-dcycloalkyld-dalkyl, d-dalkoxyd-dalkyl, d- C₅alkenyloxyCi-C₅alkyl, C3-C₅alkynyloxyCi-C₅alkyl, Ci-C₅alkylthioCi-C₅alkyl, C

C₅alkylsulfinylCi-C₅alkyl, Ci-C₅alkylsulfonylCi-C₅alkyl, C2-C₈alkylideneaminoxyCi-C₅alkyl, Ci-C₅alkylcarbonylCi-C₅alkyl, Ci-C₅alkoxycarbonylCi-C₅alkyl, aminocarbonylCrC₅alkyl, d- C₅alkylaminocarbonylCi-C₅alkyl, C2-C₈dialkylaminocarbonylCi-C₅alkyl, d- C₅alkylcarbonylaminoCi-C₅alkyl, /V-Ci-C₅alkylcarbonyl-/V-Ci-C₅alkylaminoCi-C₅alkyl, C₃- C₆trialkylsilylCi-C₅alkyl, phenylCrC₅alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, CrC₃alkyl, CrC₃fluoroalkyl, CrC₃alkoxy, Ci-C₃fluoroalkoxy, C C₃alkylthio, CrC₃alkylsulfinyl, CrC₃alkylsulfonyl, halogen, cyano, or by nitro), heteroaryld- dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d- C₃alkyl, d-C₃fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkyl-thio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₃-C₅fluoroalkenyl, d-dcycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-d alkyl, d-₃fluoroalkyl, d-C₃alkoxy, d- dfluoroalkoxy, halogen, cyano or nitro; and

R^c and R^d are each independently of each other hydrogen, d-d₀alkyl, d-Ci₀alkenyl [e.g. d-dalkenyl-CH₂- or d-dalkenyl-CH(Me)-], d-Ci₀alkynyl [e.g. d-dalkynyl-CH₂- or d-dalkynyl-CH(Me)-], d-Ci₀fluoroalkyl, d-d₀cyanoalkyl, Ci-Ci₀nitroalkyl, d- Cioaminoalkyl, d-dalkylaminod-dalkyl, d-ddialkylaminod-dalkyl, d-dcycloalkyld- dalkyl, d-dalkoxyd-dalkyl, d-dalkenyloxyd-dalkyl, C₃-C₅alkynyloxyd-C₅alkyl, d- dalkylthiod-dalkyl, d-dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl, C₂- dalkylideneaminoxyd-dalkyl, d-dalkylcarbonyld-dalkyl, d-dalkoxycarbonyld- dalkyl, aminocarbonyld-dalkyl, d-dalkylaminocarbonyld-dalkyl, d- ddialkylaminocarbonylCrdalkyl, d-dalkylcarbonylaminoCrdalkyl, /V-d- dalkylcarbonyl-/V-d-dalkylaminoalkyl, d-dtrialkylsilyld-dalkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d- dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), d-dfluoroalkenyl, d-dcycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by 1 , 2 or 3 of, independently, CrC₃alkyl, CrC₃fluoroalkyl, CrC₃alkoxy, CrC₃fluoroalkoxy, halogen, cyano or nitro;

diheteroarylamino or diheteroarylamino substituted by 1 , 2 or 3 of, independently, d- C₃alkyl, Ci-C₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or nitro;

phenylamino or phenylamino substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, d- C₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, CrC₃fluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, halogen, cyano or by nitro; or C₃-C₇cycloalkylamino, di(C₃- dcycloalkyl)amino or d-dcycloalkoxy;

or R^c and R^d, together with the nitrogen to which they are bonded, form an unsubstituted 4, 5, 6 or 7 (e.g. 5 or 6) membered ring, optionally containing one heteroatom being O or S; and

R^e is d-doalkyl, C₂-d₀alkenyl, C₂-d₀alkynyl, d-d₀fluoroalkyl, d-d₀cyanoalkyl, d- donitroalkyl, Ci-Ci₀aminoalkyl, d-dalkylaminod-dalkyl, d-ddialkylaminod-dalkyl, C₃- dcycloalkylCrdalkyl, d-dalkoxyd-dalkyl, d-dalkenyloxyd-dalkyl, d- dalkynyloxyd-dalkyl, d-dalkylthiod-dalkyl, d-dalkylsulfinyld-dalkyl, C

dalkylsulfonylCrdalkyl, d-dalkylideneaminoxyd-dalkyl, d-dalkylcarbonyld-dalkyl, d-dalkoxycarbonyld-dalkyl, aminocarbonyld-dalkyl, d-dalkylaminocarbonyld- dalkyl, d-ddialkylaminocarbonyld-dalkyl, d-dalkylcarbonylaminod-dalkyl, /V-d- dalkylcarbonyl-/V-Ci-dalkylaminoCrdalkyl, C₃-C₆trialkylsilyld-C₅alkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d- dfluoroalkyl, d-dalkoxy, d-C₃fluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, d-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-d alkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-C₃fluoroalkoxy, halogen, cyano or by nitro; heteroarylamino or heteroarylamino substituted by 1 , 2 or 3 of, independently, d-C₃ alkyl, d-dfluoroalkyl, d-C₃alkoxy, d-C₃fluoroalkoxy, halogen, cyano or by nitro;

diheteroarylamino or diheteroarylamino substituted by 1 , 2 or 3 of, independently, d-C₃ alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;

phenylamino or phenylamino substituted by 1 , 2 or 3 of, independently, d-dalkyl, d- C₃fluoroalkyl, CrC₃alkoxy, CrC₃fluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, Ci-C₃fluoroalkyl, d- C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or nitro; or C₃-C₇cycloalkylamino, di(C₃- C₇cycloalkyl)amino, C₃-C₇cycloalkoxy, CrCi₀alkoxy, Ci-Ci₀fluoroalkoxy, Ci-C₅alkylamino or C₂-C₈dialkylamino;

R and R⁹ are are each independently of each other Ci-Ci₀alkyl, C₂-Ci₀alkenyl, C₂- Ci₀alkynyl, CrCi₀alkoxy, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, CrCi₀nitroalkyl, d- Ci₀aminoalkyl, Ci-C₅alkylaminoCi-C₅alkyl, C2-C₈dialkylaminoCi-C₅alkyl, C₃-C₇cycloalkylCr C₅alkyl, Ci-C₅alkoxyCi-C₅alkyl, C₃-C₅alkenyloxyCi-C₅alkyl, C₃-C₅alkynyloxyCi-C₅alkyl, d- dalkylthiod-dalkyl, d-dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl, C₂- C₈alkylideneaminoxyCi-dalkyl, d-dalkylcarbonyld-dalkyl, d-dalkoxycarbonyld- dalkyl, aminocarbonyld-dalkyl, d-dalkylaminocarbonyld-dalkyl, C₂- CsdialkylaminocarbonylCrdalkyl, d-dalkylcarbonylaminod-dalkyl, /V-d- dalkylcarbonyl-/V-d-dalkylaminoalkyl, C₃-C₆trialkylsilyld-C₅alkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d- dfluoroalkyl, d-dalkoxy, d-C₃fluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, d-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-d alkyl, d-C₃fluoroalkyl, d-dalkoxy, d-C₃fluoroalkoxy, halogen, cyano or by nitro; heteroarylamino or heteroarylamino substituted by 1 , 2 or 3 of, independently, d-C₃ alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or by nitro;

phenylamino or phenylamino substituted by 1 , 2 or 3 of, independently, d-dalkyl, d- dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; or d-dcycloalkylamino, di(C₃- C₇cycloalkyl)amino, C₃-C₇cycloalkoxy, d-d₀fluoroalkoxy, Crdalkylamino or C₂- ddialkylamino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, CrC₃fluoroalkyl, d- C₃alkoxy, CrC₃fluoroalkoxy, halogen, cyano or nitro; and

R^h is Ci-Cioalkyl, C₃-Ci₀alkenyl [e.g. C₂-C₉alkenyl-CH₂- or C₂-C₈alkenyl-CH(Me)-],

C₃-Ci₀alkynyl [e.g. C₂-C₉alkynyl-CH₂- or C₂-C₈alkynyl-CH(Me)-], C Ci₀fluoroalkyl, C

Ciocyanoalkyl, CrCi₀nitroalkyl, C₂-Ci₀aminoalkyl, Ci-C₅alkylaminoCi-C₅alkyl, C₂- C₈dialkylaminoCi-C₅alkyl, C₃-C₇cycloalkylCi-C₅alkyl, Ci-C₅alkoxyCi-C₅alkyl, C₃- C₅alkenyloxyCi-C₅alkyl, C₃-C₅alkynyloxyCi-C₅alkyl, Ci-C₅alkylthioCi-C₅alkyl, d- C₅alkylsulfinylCi-C₅alkyl, Ci-C₅alkylsulfonylCi-C₅alkyl, C₂-C₈alkylideneaminoxyCi-C₅alkyl, Ci-C₅alkylcarbonylCi-C₅alkyl, Ci-C₅alkoxycarbonylCi-C₅alkyl, aminocarbonylCi-C₅alkyl, d- dalkylaminocarbonylCrdalkyl, C₂-C₈dialkylaminocarbonyld-C₅alkyl, d- dalkylcarbonylaminoCrdalkyl, /V-d-dalkylcarbonyl-/V-d-dalkylaminod-dalkyl, d- C₆trialkylsilylCi-C₅alkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-dfluoroalkoxy, d- dalkylthio, d-dalkylsulfinyl, d-d alkylsulfonyl, halogen, cyano or by nitro), heteroaryld- dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d- dalkyl, d-C₃fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃ alkylsulfonyl, halogen, cyano or by nitro), phenoxyd-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-C₃fluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d- alkylsulfonyl, halogen, cyano or by nitro), heteroaryloxyd-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dakylsulfinyl, d- alkylsulfonyl, halogen, cyano or by nitro), C₃- dfluoroalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of,

independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen or by nitro; or heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-dalkyl, d- dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or by nitro; wherein the term "heteroaryl" means an aromatic ring system containing at least one ring heteroatom and consisting either of a single ring or of two fused rings; and provided that, when R² is methyl or ethyl, R⁴ is methyl, R⁶ is ethynyl, and A is NH, then G is a latentiating group;

and provided that, when R² is methyl or ethyl, R⁴ is ethynyl, R⁶ is methyl, and A is NH, then G is a latentiating group. In the compounds of the formula I, each alkyl moiety either alone or as part of a larger group is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl and n-hexyl.

Alkoxy groups preferably have a preferred chain length of from 1 to 6 carbon atoms.

Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec- butoxy or tert-butoxy. Such groups can be part of a larger group such as alkoxyalkyl and alkoxyalkoxyalkyl. Alkoxyalkyl and alkylthioalkyi groups preferably have a chain length of 1 to 4 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl,

ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl or isopropoxymethyl. In alkylthioalkyi groups, oxygen is replaced by sulphur.

"Halogen" means fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or haloalkenyl.

FluoroalkyI (or floroalkenyl) groups are alkyl (or alkenyl) groups substituted by one or more (e.g. 1 , 2, 3, 4 or 5, e.g. 1 , 2 or 3, e.g. 1 or 2) fluorine atoms. FluoroalkyI groups preferably have a chain length of from 1 to 4, e.g. 1 or 2, carbon atoms (i.e. Ci_-4 or Ci_-2 fluoroalkyl). FluoroalkyI is typically (mono)fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2- trifluoroethyl, 2-fluoroethyl, pentafluoroethyl, or 2,2,3, 3-tetrafluoroethyl; preferably difluoromethyl or trifluoromethyl. Fluoroalkenyl groups are typically C_2-4 or C_2-3

fluoroalkenyl such as 2,2-difluoroethenyl or 3,3-difluoroprop-2-en-1 -yl. Chloroalkenyl groups are alkenyl groups substituted by one or more (e.g. e.g. 1 , 2 or 3, e.g. 1 or 2) chlorine atoms, for example C_2-3chloroalkenyl such as 2,2-dichloroethenyl or 3,3- dichloroprop-2-en-1 -yl.

The preferred alkenyl and/or alkynyl radicals having 2 to 6 (e.g. 2 to 4, or 2 to 3) carbon atoms can be straight or branched and can contain 1 , or more than 1 , (preferably 1 ) double or triple bond. Typically, the alkenyl or alkynyl is vinyl, (E)- or (Z)-propenyl, 2-methyl- propenyl, allyl, ethynyl, prop-1 -ynyl, propargyl, butenyl, or butynyl; more typically vinyl, (E)- or (Z)-propenyl, allyl, ethynyl, prop-1 -ynyl, or propargyl; preferably vinyl, ethynyl or prop-1 - ynyl. The cycloalkyl and/or cycloalkylalkyl groups preferably have from 3 to 6 (e.g. 3 to 5) ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In these rings, in certain cases where it is explicitly stated so, a methylene group can be replaced by a heteroatom such as oxygen, sulphur, or nitrogen in form of a group NR₀, where R₀ is Ci_-4alkyl or Ci_-4alkoxy, which leads, for example, to oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydropyran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydro-thiofuranyl, tetrahydro-thiopyranyl, N-(Ci_-4)alkyl-piperidinyl or N-(Ci_-4)alkoxy- piperidinyl rings. Cycloalkylalkyl and/or furanylalkyl groups preferably have an alkyl chain length of 1 to 4 (more preferably 1 ) carbon atoms. Cycloalkylalkyl is typically

cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl. Furanylalkyl is typically furan-2-ylmethyl or furan-3-ylmethyl. The same applies when a methylene group in the cycloalkyl moiety is replaced by O, S or NR₀, where R₀ is Ci_-4alkyl or d.

4alkoxy, to form groups such as, for example, oxetan-3-ylmethyl, tetrahydrofuran-2- ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-3- ylmethyl, tetrahydropyran-4-ylmethyl or tetrahydro-thiopyran-4-ylmethyl.

Phenyl or benzyl may be substituted on the ring (where explicitly stated to be optionally substituted), preferably by alkyl, fluoroalkyi, halogen or cyano groups. The phenyl or benzyl ring substituents can typically be in the ortho, meta and/or para position(s), such as the ortho and/or para positions.

The term "heteroaryl" means an aromatic ring system containing at least one ring heteroatom and consisting either of a single ring or of two fused rings (i.e. is monocyclic or fused bicyclic). Preferably, single rings will contain up to three ring heteroatoms and bicyclic systems up to four ring heteroatoms, which will preferably be chosen from nitrogen, oxygen and sulfur. Typically, the "heteroaryl" is furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,

1 .2.3- triazolyl, 1 ,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1 ,2,4-oxadiazolyl,

1 .3.4- oxadiazolyl, 1 ,2,5-oxadiazolyl, 1 ,2,3-thiadiazolyl, 1 ,2,4-thiadiazolyl, 1 ,3,4-thiadiazolyl,

1 .2.5- thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1 ,2,3-triazinyl, 1 ,2,4-triazinyl, 1 ,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1 ,3-benzoxadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl (e.g. 1 ,8-naphthyridinyl), benzotriazinyl, purinyl, pteridinyl or indolizinyl. The term "aryl" preferably means phenyl or naphthyl, more preferably phenyl. When G is a latentiating group, G is generally selected to allow its removal by one or a combination of biochemical, chemical or physical (e.g. plant biochemical) processes to afford compounds of formula I where G is hydrogen, e.g. during or following (e.g. following) application to the treated area or to plants. Examples of these processes include enzymatic cleavage (e.g. in a plant), chemical hydrolysis and photolysis. Compounds bearing such latentiating groups G may sometimes offer certain advantages, such as improved penetration of the cuticula of the plants treated, increased tolerance of crops, improved compatibility or stability in formulated mixtures containing other active ingredients (e.g. other herbicides), and/or reduced leaching in soils; in particular improved penetration of the cuticula of the plants treated.

Depending on the nature of the substituents, compounds of formula I may exist in different isomeric forms. When G is hydrogen, for example, compounds of formula I may exist in different tautomeric forms:

This invention covers all such isomers and tautomers and mixtures thereof in all proportions. Also, when substituents contain double bonds, c/^'s- and irans-isomers can exist. These isomers, too, are within the scope of the claimed compounds of the formula I.

The invention relates also to the agriculturally acceptable salts which the compounds of formula I are able to form with transition metal, alkali metal and alkaline earth metal bases, amines, quaternary ammonium bases or tertiary sulfonium bases.

Among the transition metal, alkali metal and alkaline earth metal salt formers, special mention should be made of the hydroxides of copper, iron, lithium, sodium, potassium, magnesium and calcium, and preferably the hydroxides, bicarbonates and carbonates of sodium and potassium. Examples of amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary Ci-Ci₈alkylamines, Ci-C₄hydroxyalkylamines and

C₂-C₄alkoxyalkyl-amines, for example methylamine, ethylamine, n-propylamine, /^'- propylamine, the four butylamine isomers, n-amylamine, /^'-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine,

methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-/-propylamine, di-n-butylamine, di-n- amylamine, di-/-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n- propanolamine, /-propanolamine, Λ/,/V-diethanolamine, /V-ethylpropanolamine, N- butylethanolamine, allylamine, n-but-2-enylamine, n-pent-2-enylamine, 2,3-dimethylbut-2- enylamine, dibut-2-enylamine, n-hex-2-enylamine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tri-/^'-opropylamine, tri-n-butylamine, tri-/^'-butylamine, tri-sec- butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines,

methoxyanilines, ethoxyanilines, o, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o, m- and p-chloroanilines; but especially triethylamine,

/^'-propylamine and di-/-propylamine.

Preferred quaternary ammonium bases suitable for salt formation correspond, for example, to the formula [N(R_a R_b R_c R_d)]OH, wherein R_a, R_b, R_c and R_d are each independently of the others hydrogen or Ci-C₄alkyl. Further suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

Preferred tertiary sulfonium bases suitable for salt formation correspond, for example, to the formula [SR_eR_fR_g]OH, wherein R_e, R_f and R_g are each independently of the others C C₄ alkyl. Trimethylsulfonium hydroxide is especially preferred. Suitable sulfonium bases may be obtained from the reaction of thioethers, in particular dialkylsulfides, with alkylhalides, followed by conversion to a suitable base, for example a hydroxide, by anion exchange reactions. It should be understood that in those compounds of formula I, where G is a metal, ammonium or sulfonium as mentioned above and as such represents a cation, the corresponding negative charge is largely delocalised across the 0-C=C-C=0 unit. The compounds of formula I according to the invention also include hydrates which may be formed during the salt formation.

The preferred values of R, A, G, R², R⁴, R⁵, and/or R⁶, in the compounds of formula I are set out below, and can be taken together in any combination(s) thereof.

Preferably, R is hydrogen, Ci_-4alkyl, Ci_-2fluoroalkyl, Ci_-2cyanoalkyl, C₂-₃alkenyl-CH₂-, C_2-3alkenyl-CH(Me)-, C_2-3fluoroalkenyl-CH₂-, C₂chloroalkenyl-CH₂-, C_2-3alkynyl-CH₂-, benzyl, Ci_-2alkoxy(Ci_-2)alkyl or Ci_-2alkoxy-CH₂CH₂0-(Ci_-2)alkyl. More preferably, R is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyanomethyl,

trifluoromethyl, 2,2,2-trifluoroethyl, allyl, 3,3-dichloroallyl, propargyl, benzyl, methoxymethyl, ethoxymethyl, methoxyethyl or (2-methoxy-ethoxy)methyl. Still more preferably, R is hydrogen, methyl, ethyl, n-propyl, or isopropyl. Most preferably, R is methyl or ethyl, in particular methyl.

Preferably, A is either NR¹ or NOR¹ (in particular NR¹), wherein

R¹ is hydrogen, Ci_-4alkyl, Ci_-2fluoroalkyl, C₃-₆cycloalkyl, or C_4-6cycloalkyl wherein in the cycloalkyl moiety one methylene group is replaced by O, S or NR₀, wherein R₀ is Ci_-3alkyl or Ci_-3alkoxy (e.g. methyl),

or R¹ is C_3-6cycloalkyl(Ci-₂)alkyl-, or C₄-₆cycloalkyl(Ci_-2)alkyl- wherein in the cycloalkyl moiety one methylene group is replaced by O, S or NR₀, wherein R₀ is Ci_-3alkyl or

Ci_-3alkoxy (e.g. methyl),

or R¹ is C_2-3alkenyl-CH₂-, C_2-3alkenyl-CH(Me)-, C_2-3fluoroalkenyl-CH₂-,

C₂chloroalkenyl-CH₂-, C_2-3alkynyl-CH₂-, Ci_-2cyanoalkyl, benzyl, furanylmethyl-,

Ci_-2alkoxy(Ci_-3)alkyl or Ci_-2alkoxy-CH₂CH₂0-(Ci_-2)alkyl;

provided that, when both R⁴ and R⁶ are hydrogen, then A is NR¹ and R¹ is hydrogen. More preferably, A is either NR¹ or NOR¹ (in particular NR¹), wherein R¹ is hydrogen, Ci_-3alkyl, C_3-6cycloalkyl (e.g. cyclopropyl), or C_5-6cycloalkyl wherein in the cycloalkyl moiety one methylene group is replaced by O or S (e.g. O),

or R¹ is C₃-₆cycloalkylmethyl- (e.g. cyclopropylmethyl-), or C₅-₆cycloalkylmethyl- wherein in the cycloalkyl moiety one methylene group is replaced by O or S (e.g. O),

or R¹ is CH₂=CH-CH₂- (allyl), ethynyl-CH₂- (propargyl), methoxy(Ci_-2)alkyl or

methoxy-CH₂CH₂0-(Ci_-2)alkyl;

provided that, when both R⁴ and R⁶ are hydrogen, then A is NR¹ and R¹ is hydrogen.

In a particular embodiment, A is either NR¹ or NOR¹ (in particular NR¹), wherein R¹ is hydrogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2- difluoroethyl, 2-fluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,

cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, allyl, propargyl, benzyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxypropyl,

(2-methoxy-ethoxy)methyl, 2-(methoxymethoxy)ethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydropyran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-4-yl, 1 -methoxy-piperidin-4-yl, oxetan-3-ylmethyl-, tetrahydrofuran-2- ylmethyl-, tetrahydropyran-2-ylmethyl-, tetrahydrofuran-3-ylmethyl-, tetrahydropyran-3- ylmethyl-, tetrahydropyran-4-ylmethyl-, 2-methylthio-ethyl, 2-methanesulfinyl-ethyl, 2- methanesulfonyl-ethyl, furan-2-ylmethyl, furan-3-ylmethyl or tetrahydro-thiopyran-4- ylmethyl;

More preferably, A is either NR¹ or NOR¹ (in particular NR¹), wherein R¹ is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, allyl, propargyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxypropyl, (2-methoxy-ethoxy)methyl, tetrahydrofuran-2-yl, tetrahydropyran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-4-yl, tetrahydrofuran-2-ylmethyl-,

tetrahydropyran-2-ylmethyl-, tetrahydrofuran-3-ylmethyl-, tetrahydropyran-3-ylmethyl-, tetrahydropyran-4-ylmethyl-, or 2-methylthio-ethyl;

More preferably, A is either NR¹ or NOR¹ (in particular NR¹), wherein R¹ is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, allyl, propargyl or methoxymethyl;

provided that, when both R⁴ and R⁶ are hydrogen, then A is NR¹ and R¹ is hydrogen. Even more preferably, A is either NR¹ or NOR¹ (in particular NR¹), wherein R¹ is hydrogen, methyl or ethyl (in particular hydrogen or methyl);

In all aspects of the invention, preferably, A is NR¹.

In all aspects of the invention, most preferably, A is NR¹ and R¹ is hydrogen.

Preferably, when G is a latentiating group, then G is -C(X^a)-R^a or -C(X^b)-X^c-R^b, and the meanings of X^a, R^a, X^b, X^c and R^b are as defined herein.

Preferably, R^a is CrCi₀alkyl (e.g. d-C₆alkyl), C₂-C₆alkenyl (e.g. C₂-C₄alkenyl), C₂-C₆alkynyl (e.g. C₂-C₄alkynyl), C₃-C₆cycloalkyl or Ci-C₄alkoxyCi-C₄alkyl.

Preferably, R^b is C Ci₀alkyl (e.g. C C₆alkyl), C₂-C₅alkenyl-CH₂- (e.g. C₂-C₃alkenyl-CH₂-), C₂-C₄alkenyl-CH(Me)- (e.g. C₂-C₃alkenyl-CH(Me)-), C₂-C₅alkynyl-CH₂- (e.g.

C₂-C₃alkynyl-CH₂-), C₂-C₄alkynyl-CH(Me)- (e.g. C₂-C₃alkynyl-CH(Me)-), C₃-C₆cycloalkyl or Ci-C₄alkoxyCi-C₄alkyl.

More preferably, when G is a latentiating group, then G is -C(X^a)-R^a or -C(X^b)-X^c-R^b, wherein X^a, X^b and X^c are oxygen; R^a is Ci-Cioalkyl (e.g. C C₆alkyl), C₂-C₆alkenyl (e.g. C₂- C₄alkenyl), C₂-C₆alkynyl (e.g. C₂-C₄alkynyl), C₃-C₆cycloalkyl or Ci-C₄alkoxyCi-C₄alkyl; and R^b is Ci-Ci₀alkyl (e.g. C C₆alkyl), C₂-C₅alkenyl-CH₂- (e.g. C₂-C₃alkenyl-CH₂-),

C₂-C₄alkenyl-CH(Me)- (e.g. C₂-C₃alkenyl-CH(Me)-), C₂-C₅alkynyl-CH₂- (e.g.

C₂-C₃alkynyl-CH₂-), C₂-C₄alkynyl-CH(Me)- (e.g. C₂-C₃alkynyl-CH(Me)-), C₃-C₆cycloalkyl or Ci -C₄a I koxy Ci -C₄a I ky I . It is also preferred that G is hydrogen, an alkali metal or an alkaline earth metal, or an ammonium or sulfonium group.

More preferably, G is hydrogen, or a latentiating group which is -C(X^a)-R^a or -C(X^b)-X^c-R^b. Most preferably G is hydrogen. In the following preferable features for R², R⁴, R⁵ and/or R⁶, it is always the case, as stated elsewhere herein, that:

either (i) one or both of R² and R⁶ is or are, independently, C_2-3alkynyl,

and/or (ii) R⁴ is C_2-4alkynyl;

and one, two or all of of R⁴, R⁵ and R⁶ is or are not hydrogen;

and, when R⁴ is not hydrogen, then R⁵ is hydrogen or Ci_-2alkyl;

and, when both R⁴ and R⁶ are hydrogen, then A is NR¹ and R¹ is hydrogen.

Preferably, R² is methyl, ethyl, vinyl, ethynyl, cyclopropyl, CifluoroalkyI (e.g. CF₃), methoxy, Cifluoroalkoxy (e.g. CF₃0, CHF₂0 or CH₂FO), fluoro, bromo or chloro.

More preferably, R² is methyl, ethyl, vinyl, ethynyl, cyclopropyl, Cifluoroalkoxy (e.g. CF₃0, CHF₂0 or CH₂FO), bromo or chloro. Even more preferably, R² is methyl, ethyl or ethynyl.

Most preferably, R² is methyl or ethynyl, in particular methyl.

Preferably, R⁴ is hydrogen, Ci_-3alkyl, vinyl, (£)-prop-1 -enyl, (Z)-prop-l -enyl, ethynyl, prop-1 -ynyl, CifluoroalkyI, methoxy, Cifluoroalkoxy, halogen (e.g. F, CI or Br); or phenyl or phenyl substituted by 1 , 2 or 3 of, independently, methyl, CifluoroalkyI, methoxy,

Cifluoroalkoxy or halogen.

When R⁴ is phenyl or substituted phenyl, then preferably either R⁴ is phenyl, or R⁴ is phenyl substituted at the para-position by halogen (in particular chloro) and optionally further substituted by 1 or 2 of, independently, methyl, CifluoroalkyI, methoxy,

Cifluoroalkoxy or halogen. More preferably, when R⁴ is phenyl or substituted phenyl, then preferably either R⁴ is phenyl, or R⁴ is phenyl substituted at the para-position by halogen (in particular fluoro, chloro or bromo; or more particularly chloro) and optionally further substituted by 1 halogen (e.g. chloro or fluoro).

More preferably, R⁴ is hydrogen, Ci_-2alkyl, vinyl, (£)-prop-1 -enyl, (Z)-prop-l -enyl, ethynyl or prop-1 -ynyl. Even more preferably, R⁴ is methyl, ethynyl or prop-1 -ynyl, in particular ethynyl or prop-1 -ynyl.

Most preferably, R⁴ is prop-1 -ynyl.

When R⁴ is prop-1 -ynyl (which is preferred), then, preferably, R² is methyl and/or R⁶ is methyl, or most preferably R² and R⁶ are methyl.

Preferably, R⁵ is hydrogen or Ci_-2alkyl; or R⁵ is phenyl or phenyl substituted by 1 , 2 or 3 of, independently, methyl, CifluoroalkyI, methoxy, Cifluoroalkoxy or halogen.

Preferably, when R⁵ is phenyl or substituted phenyl, then either R⁵ is phenyl, or more preferably R⁵ is phenyl substituted at the para-position by halogen (in particular chloro) and optionally further substituted by 1 or 2 of, independently, methyl, CifluoroalkyI, methoxy, Cifluoroalkoxy or halogen. More preferably, when R⁵ is phenyl or substituted phenyl, then either R⁵ is phenyl, or still more preferably R⁵ is phenyl substituted at the para-position by halogen (in particular fluoro, chloro or bromo; or more particularly chloro) and optionally further substituted by 1 halogen (e.g. chloro or fluoro).

More preferably, R⁵ is hydrogen or Ci_-2alkyl, in particular hydrogen or methyl.

Most preferably, R⁵ is hydrogen.

Preferably, when R⁴ is not hydrogen, then R⁵ is hydrogen or methyl, more preferably hydrogen.

Preferably, R⁶ is hydrogen, methyl, ethyl, vinyl, ethynyl, CifluoroalkyI (e.g. CF₃), methoxy, Cifluoroalkoxy (e.g. CF₃0, CHF₂0 or CH₂FO), fluoro, bromo or chloro.

More preferably, R⁶ is methyl, ethyl, vinyl, ethynyl, Cifluoroalkoxy (e.g. CF₃0, CHF₂0 or CH₂FO), bromo or chloro. Even more preferably, R⁶ is methyl, ethyl or ethynyl.

Most preferably, R⁶ is methyl or ethynyl. Preferably, R⁴ and R⁶ are not hydrogen. More preferably, R⁴ and R⁶ are not hydrogen, and R⁵ is hydrogen.

Preferably, either (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl,

and/or (ii) R⁴ is C_2-4alkynyl. In a particular embodiment, either (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl, or (ii) R⁴ is C_2-4alkynyl.

Preferably, (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl; and/or (ii) R⁴ is ethynyl or prop-1 -ynyl. In a particular embodiment, either (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl, or (ii) R⁴ is ethynyl or prop-1 -ynyl.

More preferably, (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl; and/or (ii) R⁴ is ethynyl or prop-1 -ynyl. In a particular embodiment, either (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl, or (ii) R⁴ is ethynyl or prop-1 -ynyl.

Most preferably, (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl; and/or (ii) R⁴ is prop-1 -ynyl. In a particular embodiment, either (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl, or (ii) R⁴ is prop-1 -ynyl.

More preferably, R² and R⁶ are, independently, methyl or ethynyl; R⁴ is methyl, ethynyl or prop-1 -ynyl; and R⁵ is hydrogen;

provided that (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl; and/or (ii) R⁴ is ethynyl or prop-1 -ynyl.

Even more preferably, R² and R⁶ are, independently, methyl or ethynyl; R⁴ is methyl or prop-1 -ynyl; and R⁵ is hydrogen;

provided that (i) one or both (e.g. one) of R² and R⁶ is or are ethynyl; and/or (ii) R⁴ is prop-1 -ynyl.

Most preferably, R² and R⁶ are, independently, methyl or ethynyl (preferably methyl); R⁴ is prop-1 -ynyl; and R⁵ is hydrogen. In the invention, when R² is methyl or ethyl, R⁴ is methyl, R⁶ is ethynyl, and A is NH, then G is a latentiating group (preferably -C(X^a)-R^a or -C(X^b)-X^c-R^b);

and when R² is methyl or ethyl, R⁴ is ethynyl, R⁶ is methyl, and A is NH, then G is a latentiating group (preferably -C(X^a)-R^a or -C(X^b)-X^c-R^b).

Preferably, when R² is methyl or ethyl, R⁴ is methyl, R⁶ is ethynyl, then A is not NH;

and when R² is methyl or ethyl, R⁴ is ethynyl, R⁶ is methyl, then A is not NH.

Preferably, when R² is Ci_-3alkyl, C_2-3alkenyl, cyclopropyl or Ci_-2fluoroalkyl, R⁴ is hydrogen, Ci_-4alkyl, C_2-4alkenyl, C₃-₆cycloalkyl or Ci_-2fluoroalkyl, and R⁶ is ethynyl; then either (i) A is not NH or (ii) A is NH and G is a latentiating group (preferably -C(X^a)-R^a or -C(X^b)-X^c-R^b); and/or

when R⁴ is ethynyl, R² is Ci_-3alkyl, C_2-3alkenyl, cyclopropyl or Ci_-2fluoroalkyl, and R⁶ is hydrogen, Ci_-3alkyl, C_2-3alkenyl, cyclopropyl or Ci_-2fluoroalkyl; then either (i) A is not NH or (ii) A is NH and G is a latentiating group (preferably -C(X^a)-R^a or -C(X^b)-X^c-R^b);.

Especially preferably, R⁴ is not ethynyl.

Especially preferably, when R⁶ is ethynyl, then: G is a latentiating group (preferably -C(X^a)- R^a or -C(X^b)-X^c-R^b), and/or R² and R⁶ are both ethynyl.

In a particular embodiment of all aspects of the invention, the compound of the formula (I) or the agrochemically acceptable salt thereof is a compound as illustrated and/or disclosed in any one of Tables 1 to 333 herein, or an agrochemically acceptable salt thereof.

In a particularly preferable embodiment of all aspects of the invention, the compound of the formula (I) or the agrochemically acceptable salt thereof is compound P1 .7, P1 .8, P1 .9, P1 .10, P1 .12, P1 .13, P1 .14, P1 .15, P2.7, P2.8, P2.9, P2.12, P2.13 or P2.14, as illustrated and/or disclosed herein, or an agrochemically acceptable salt thereof; more preferably compound P1 .7, P1 .8, P1 .9, P1 .12, P1 .13, P1 .14, P1 .15, P2.7, P2.8, P2.13 or P2.14, or an agrochemically acceptable salt thereof; most preferably P1 .7, P1.12, P1 .14, P1 .15, P2.13 or P2.14, or an agrochemically acceptable salt thereof.

The invention covers also salts of the compounds of the formula I with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides as salt formers, special mention should be made of the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially the hydroxides of sodium and potassium. The compounds of formula I according to the invention also include hydrates which may be formed during the salt formation.

Examples of amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary Ci-Ci₈alkylamines, Ci-C₄hydroxyalkylamines and

C₂-C₄alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine,

isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine,

methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n- amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n- propanolamine, isopropanolamine, Ν,Ν-diethanolamine, N-ethylpropanolamine, N- butylethanolamine, allylamine, n-but-2-enylamine, n-pent-2-enylamine, 2,3-dimethylbut-2- enylamine, dibut-2-enylamine, n-hex-2-enylamine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec- butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines,

methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but especially triethylamine,

isopropylamine and diisopropylamine.

Preferred quaternary ammonium bases suitable for salt formation correspond, for example, to the formula [N(R_a R_b R_c Rd)]OH wherein R_a, R_b, R_c and R_d are each independently of the others CrC₄alkyl. Further suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

Processes for preparation of compounds The compounds of the invention may be made by a variety of methods. For example, the compounds of formula I , wherein the substituents have the meanings assigned to them above, can be prepared by means of processes known per se, e.g. by treating compounds of formula II with an alkylating, acylating, phosphorylating or sulfonylating agent G-Q in the presence of at least one equivalent of a base, where G is the alkyl, acyl, phosphoryl or sulfonyl group to be incorporated and Q is a nucleofuge:

(II) (I)

Compounds of formula I, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein and wherein G is a latentiating group of the formula -C(X^a)-R^a, -C(X^b)X^c-R^b or -C(X^d)-NR^cR^d may be prepared e.g. by procedures known in the art, e.g. as described for example in WO 2009/049851. Typically, compounds of formula II, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein, are treated with an acylating agent such as an acid halide (especially acid chloride), acid anhydride, haloformate (especially chloroformate), halothioformate

(especially chlorothioformate), isocyanate, isothiocycanate, carbamoyl halide (especially carbamoyl chloride) or thiocarbamoyl halide (especially thiocarbamoyl chloride) in the presence of at least one equivalent of a suitable base, optionally in the presence of a suitable solvent. The base may be inorganic such as an alkali metal carbonate or hydroxide or a metal hydride, or an organic base such as a tertiary amine or metal alkoxide. Examples of suitable inorganic bases include sodium carbonate, sodium or potassium hydroxide, sodium hydride, and suitable organic bases include trialkylamines such as trimethylamine and triethylamine, pyridines or other amine bases such as 1 ,4- diazobicyclo[2.2.2]octane and 1 ,8-diazabicyclo[5.4.0]undec-7-ene. Preferred bases include triethylamine and pyridine. Suitable solvents for this reaction are selected to be compatible with the reagents and include ethers such as tetrahydrofuran and 1 ,2-dimethoxyethane and halogenated solvents such as dichloromethane and chloroform. Certain bases, such as pyridine and triethylamine, may be employed successfully as both base and solvent. For cases, where the acylating agent is a carboxylic acid, acylation is preferably effected in the presence of a coupling agent such as 2-chloro-1 -methylpyridinium iodide, Ν,Ν'- dicyclohexycarbodiimide, 1 -(3-dimethylaminopropyl)-3-ethylcarbodiimide and Ν,Ν'- carbodiimidazole, and a base such as triethylamine or pyridine in a suitable solvent such as tetrahydrofuran, dichloromethane and acetonitrile. Compounds of formula I, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein and wherein G is a latentiating group of the formula -C(X^b)-X^c-R^b or -C(X^d)-NR^cR^d, may be also be prepared by treating compounds of formula II, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein, with phosgene or a phosgene equivalent, optionally in the presence of a solvent such as toluene or ethyl acetate, and a base and reacting the resultant chloroformate, or equivalent, with an alcohol, thiol or amine, e.g. under known conditions, as described, for example, in US 6774133, US 6555567 and US 6479489.

Compounds of formula I, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein and wherein G is a latentiating group of the formula -P(X^e)R R⁹, may be prepared from compounds of formula II, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein, e.g. using procedures described, for example, in US 6774133, US 6555567 and US 6479489.

Compounds of formula I, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein and wherein G is a latentiating group of the formula -S0₂R^e, may be prepared by reaction of compounds of formula II, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein, with an alkyl or aryl sulfonyl halide, preferably in the presence of at least one equivalent of base.

Compounds of formula I, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein and wherein G is CrC₆alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl or a latentiating group of the formula -CH₂-X -R^h, may be prepared by treatment of a compound of formula II, in which R, A, R², R⁴, R⁵ and R⁶ are as defined herein, with a compound of formula G-Y" wherein Y" is a halogen (especially bromine or iodine), sulfonate (especially mesylate or tosylate) or a sulfate preferably in the presence of a base, e.g. under known conditions.

Compounds of formula I , in which R, A, G, R², R⁴, R⁵ and R⁶ are as defined herein, can be obtained by treating compounds of formula I I I , in which R, A, G, R², R⁴, R⁵ and R⁶ are as defined herein, with an alkylating agent R-Q, wherein R represents the alkyl, substituted alkyl, alkenyl, alkynyl or other group to be incorporated, and Q represents a nucleofuge (e.g. leaving group), in the presence of at least one equivalent of a base, and optionally in the presence of a suitable solvent.

Compounds of formula I I I , in which A, G, R², R⁴, R⁵ and R⁶ are as defined herein,

can be obtained by catalytic hydrogenation of compounds of formula I , in which A, G, R², R⁴, R⁵ and R⁶ are as defined herein, and in which R is a benzyl group.

Compounds of formula II may be prepared via the cyclisation of compounds of formula IV,

wherein R₁₄ is Ci_-6alkyl (preferably methyl or ethyl), preferably in the presence of base, and optionally in the presence of a suitable solvent, e.g. by known methods described, for example, in WO 2009/049851 . R, A, R², R⁴, R⁵ and R⁶ are as defined herein.

(V) (VI) (IV)

Compounds of formula IV may be prepared by reacting piperidine-4-carboxylic acid derivatives of formula V with phenylacetyl halides of formula VI, preferably in the presence of base in a suitable solvent, e.g. by known methods described, for example, in WO 09/049851 . R, A, R², R⁴, R⁵, R⁶ and Ri₄ are as defined herein. The base may be inorganic such as an alkali metal carbonate or hydroxide or a metal hydride, or an organic base such as a tertiary amine or metal alkoxide. Examples of suitable inorganic bases include sodium carbonate, sodium or potassium hydroxide, sodium hydride, and suitable organic bases include trialkylamines such as trimethylamine and triethylamine, pyridines or other amine bases such as 1 ,4-diazobicyclo[2.2.2]octane and 1 ,8-diazabicyclo[5.4.0]undec-7-ene. Preferred bases include triethylamine and pyridine. Suitable solvents for this reaction are selected to be compatible with the reagents and include ethers such as tetrahydrofuran and 1 ,2-dimethoxyethane and halogenated solvents such as dichloromethane and chloroform. Certain bases, such as pyridine and triethylamine, may be employed successfully as both base and solvent. In the situation wherein A is NOH, acylation methods of a-hydroxylamino acid derivatives of formula V are of extreme advantage where N-acylation selectivity can be achieved according, for example, to Vallee and Blandin, Organic & Biomolecular Chemistry, 4, 3125-3141 , (2006) or to WO 96/35714, and whereby the use of transition metal, alkali metal, and alkaline earth metal bases is preferred. The use of a mild base, especially bicarbonates and carbonates of lithium, sodium, potassium and cesium, and more particularly lithium, sodium, potassium and cesium hydrogen carbonate, and even more particularly sodium and potassium hydrogen carbonate in solvents like dichloromethane, tetrahydrofuran, dioxane or mixtures thereof are preferred reaction conditions. The solvent system for these mild basic acylation conditions may also be aqueous biphasic employing, for example, ethyl acetate (or dichloromethane, or any related organic solvent) and water, as decribed, for example, by Ito et al., Heterocycles, 57, 881 -894, (2002). Phenylacetyl halides of formula VI, wherein Hal is CI or Br and in which R², R⁴, R⁵ and R⁶ are as defined herein, are known compounds or can e.g. be prepared by known methods, described for example in WO 2009/049851 . For the particular situation in which A is NOR¹, wherein R¹ is as defined herein, compounds of formula IVa, wherein R₁₄ is as defined above, may be prepared by treatment of a compound of formula IVb (R¹=H) with an alkylating agent of formula R¹-Y", wherein R¹ is the alkyl, substituted alkyl, alkenyl, alkynyl or other group to be incorporated and Y" is a halogen (especially bromine or iodine), sulfonate (especially mesylate or tosylate) or a sulfate, preferably in the presence of a base, under known conditions.

or R¹-Q

(IVb) (IVa)

Alternatively, compounds of formula IVa, wherein R₁₄ is as defined above and wherein R¹, R, R², R⁴, R⁵, R⁶ are as defined herein, may be prepared by treatment of a compound of formula IVb (R¹=H) with an alcohol of formula R¹-OH, wherein R¹ is the alkyl, substituted alkyl, alkenyl, alkynyl or other group to be incorporated, e.g. under the known conditions of the Mitsunobu reaction. Typically, the alcohol R¹-OH is reacted with the hydroxamic acid derivative IVb in the presence of a dialkyl azodicarboxylate (preferably diethyl

azodicarboxylate DEAD, diisopropyl azodicarboxylate DIAD, 1 ,1 '-

(azodicarbonyl)dipiperidine ADDP, Ν,Ν,Ν',Ν'-tetramethylazodicarboxamide TMAD or equivalents) and a trialkyl- or triaryl phosphine (preferably triphenyl phosphine, tributyl phosphine or equivalents) usually in solvents like tetrahydrofuran, dioxane,

dichloromethane, chloroform, dimethylformamide, toluene or benzene at -20 to 80°C, preferably at 0°C to 30°C. These known conditions are described for example by O.

Mitsunobu, Synthesis 1981 , 1 -28; B.R. Castro, Org. React. 1983, 29, 1 -162; D.L. Hughes, Org. React. 1992, 42, 335-656 or D.L. Hughes, Org. Prep. Preced. Int. 1996, 28, 127-164. Compounds of formula IVa, wherein R₁₄ is as defined above and wherein R¹ is

tetrahydrofuran-2-yl or tetrahydropyran-2-yl may be prepared by treatment of a compound of formula IVb (R¹=H) with 2,3-dihydro-furan or 3,4-dihydro-2H-pyran preferably in the presence of an acid catalyst (especially p-toluene sulfonic acic or pyridinium p- toluenesulfonate), e.g. under known conditions described for example by Shanzer at al., J.Am.C em.Soc. 129, 347-354, (2007).

(IVb) (IVa) (II), wherein A is NOR¹

Compounds of formula II, in which A is NOR¹, may also be prepared in a two-step one-pot process involving

(i) O-alkylation of compounds of formula IVb with an agent R¹-Y" or R¹-Q, where R¹ is the alkyl, substituted alkyl, alkenyl, alkynyl or other group to be incorporated and wherein Y" and Q represents a nucleofuge (e.g. leaving group) as defined above, in the presence of at least one equivalent of a base, and

(ii) cyclisation of the intermediate compounds of formula IVa, preferably in the presence of additional base, at least one more equivalent, and optionally in the presence of a suitable solvent, e.g. by methods described above.

Ri₄ is typically CrC₆ alkyl, preferably methyl or ethyl. The base for steps (i) and (ii) may be the same or different.

(VII) (V) Piperidine-4-carboxylic acid derivatives of the formula V, wherein R₁₄ is CrC₆alkyl

(preferably methyl or ethyl), may be prepared by reacting nitriles of the formula VII with an alcohol of the formula Ri₄OH, wherein R₁₄ is CrC₆alkyl (preferably methyl or ethyl), preferably in the presence of a strong acid (especially sulfuric acic or hydrochloric acid), under known conditions. For the particular situation where Ri₄ is methyl, a compound of the formula VII may also be treated with acetyl chloride in methanol. R and A are as defined herein.

Piperidine-4-carboxylic acid derivatives of the formula V, wherein R₁₄ is CrC₆alkyl (preferably methyl or ethyl), can also be prepared, e.g. by known methods, from acids of formula VIII. Esterification of VIII with an alcohol of the formula Ri₄OH, wherein R₁₄ is C C₆alkyl, under thionyl chloride activation is a typical example for the preparation of esters V, as described for example in WO 2009/049851 , but other known esterification methods may also be applied, like for example treatment of a compound of the formula VIII with an alcohol of the formula R₁₄OH under acidic conditions (typically H₂S0₄ or HCI). For the particular situation where Ri₄ is methyl, a compound of the formula VIII may also be treated with diazomethane or trimethylsilyldiazomethane, or with acetyl chloride in methanol. The compounds VIII, VII and V can be reacted and/or isolated as free amines or amine salts (e.g. a hydrohalide salt, more specifically a hydrochloride or hydrobromide salt, or any other equivalent salt).

(VII) (VI II) (V)

R₁₄-0H

H⁺

Hydrolysis of nitriles of the formula VII into acids of formula VIII is typically performed with water under acidic conditions, for example in presence of hydrochloric or sulfuric acid.

Nitriles of the formula VII, wherein R and A are as defined above, may be prepared from ketones of formula X,

wherein R is as defined above, by means of Strecker-type chemistry utilizing known methods described, for example, in WO 2010/63670 and in WO 2010/66780.

Alternatively, compounds of formula IV wherein R₁₄ is CrC₆alkyl, may be prepared by subjecting nitrile derivatives of formula XI to alcoholysis with R₁₄OH, preferably in acidic media (especially sulfuric acid or hydrochloric acid) by known methods described, for example, in WO 2009/049851 . R, A, R², R⁴, R⁵, R⁶ are as defined herein. Nitrile compounds of formula XI may be themselves prepared by reacting compounds of formula VII with phenylacetyl halides of formula VI, preferably in the presence of base in a suitable solvent by known methods described, for example, in WO 09/049851 . R, A, R², R⁴, R⁵, R⁶ are as defined herein. The base may be inorganic such as an alkali metal carbonate or hydroxide or a metal hydride, or an organic base such as a tertiary amine or metal alkoxide. Examples of suitable inorganic bases include sodium carbonate, sodium or potassium hydroxide, sodium hydride, and suitable organic bases include trialkylamines such as trimethylamine and triethylamine, pyridines or other amine bases such as 1 ,4- diazobicyclo[2.2.2]octane and 1 ,8-diazabicyclo[5.4.0]undec-7-ene. Preferred bases include triethylamine and pyridine. Suitable solvents for this reaction are selected to be compatible with the reagents and include ethers such as tetrahydrofuran and 1 ,2-dimethoxyethane and halogenated solvents such as dichloromethane and chloroform. Certain bases, such as pyridine and triethylamine, may be employed successfully as both base and solvent. These reaction conditions do also apply for the particular situation where A is NOH, allowing to prepare compounds of the formula IVb from nitriles of the formula VII, in which A is NOH, via compounds of the formula Xlb. Of extreme advantage are also acylation methods of nitrile derivatives of formula VII where N-acylation selectivity can be achieved according, for example, to Vallee and Blandin, Organic & Biomolecular Chemistry, 4, 3125- 3141 , (2006) or to WO 96/35714, and whereby the use of transition metal, alkali metal, and alkaline earth metal bases is preferred. The use of a mild base, especially

bicarbonates and carbonates of lithium, sodium, potassium and cesium, and more particularly lithium, sodium, potassium and cesium hydrogen carbonate, and even more particularly sodium and potassium hydrogen carbonate in solvents like dichloromethane, tetrahydrofuran, dioxane or mixtures thereof are preferred reaction conditions. The solvent system for these mild basic acylation conditions may also be aqueous biphasic employing, for example, ethyl acetate (or dichloromethane, or any related organic solvent) and water, as decribed, for example, by Ito et al., Heterocycles, 57, 881 -894, (2002). The

transformation of compounds of the formula Xlb into compounds of the formula IVb under alcoholysis conditions with R₁₄OH uses same conditions as described above for the conversion of compounds of the formula XI into compounds of the formula IV.

(Xla) (IVb)

Compounds of formula Xla, in which A is NOR¹, wherein R¹ is as defined herein can moreover be obtained by treating compounds of formula Xlb with agents R¹-Y", R¹-OH, R¹- Q or 2,3-dihydro-furan or 3,4-dihydro-2H-pyran, wherein R¹, Y and Q are as defined above, under the same conditions described above for the conversion of compounds of the formula IVb into compounds of the formula IVa.

The group of compounds D1 comprising compounds of the formula I, and compounds of the formula II, and intermediates of the formula IV or XI, and precursors of the compounds of the formula VI (the corresponding acids or esters), wherein at least one of R², R⁴ or R⁶ is alkenyl or alkynyl, may be prepared by reacting a corresponding halogen precursor form a group of compounds D2, R_{6 is:}

eg. Pd or Ni catalyst

(D₂) (D

Hal is chlorine, bromine or iodine, GRN is alkenyl or alkynyl

or a pseudohalogen such as triflate wherein Hal is chlorine, bromine, iodine or a pseudohalogen such as Ci_-4fluoroalkyl- sulfonate, especially triflate, by means of a transition metal-catalyzed reaction with an appropriate reaction partner. D represents one of the following fragments D3-D8:

wherein W denotes the position of attachment to the phenyl-moiety in the group of compounds of the formula D1 and D2, and in which R₁₄ is Ci_-6alkyl. A and R are as defined herein. Transition metal-catalyzed reactions, in particular under palladium- or nickel-catalyzed conditions, may be defined as a Negishi coupling (involving an organozinc reagent such as HC≡CZnBr or H₂C=CHZnCI), a Suzuki coupling (involving an organoboron reagent such as 2-ethenyl-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane; potassium

(ethenyl)trifluoroborate; or triethenylboroxin [optionally as 1 :1 -pyridine complex]), a Stille coupling (involving an organostannane reagent such as Bu₃SnCH=CH₂, Me₃SnCH=CH₂ [see for example J. Org. C em. 52, 422-4 (1988)], or tributyl(l -ethoxyvinyl)tin), a Kumada coupling (involving an Grignard reagent such as H₂C=CHMgCI), a Hiyama coupling (involving an organosilicon reagent such as ethenyltrimethyl-silane or alkenylsilanolates), a Sonogashira reaction (involving a terminal alkyne reagent such as ethynyltrimethyl-silane or 2-methyl-but-3-yn-2-ol), a Heck reaction (involving an olefin reagent such as ethylene under pressure, see for example C.R. Smith et al., Tetrahedron 66, 1 102-1 1 10 (2010), a carbonylation reaction (in particular an alkoxycarbonylation involving carbon monoxide (or another source of CO, such as for example molybdenum hexacarbonyl) and an alcohol R₁₄OH) or other related and known reactions from the literature. Further details on metal- catalyzed cross-coupling conditions may be found, for example in Metal-catalyzed Cross- coupling Reactions, ed. by Diederich F, Stang PJ, Wiley-VCH, Weinheim, (1998) or Modern Arylation Methods, ed. by Ackermann L, Wiley-VCH, Weinheim, (2009). An additional hydrolysis or deprotection, in particular desilylation, step may be necessary to convert the direct product of the transition metal-catalyzed reaction into a compound of the formula D-i , wherein at least one of R², R⁴ or R⁶ is alkenyl or alkynyl.

Worthwhile mentioning are the following particular example:

(a) Sonogashira reaction with ethynyltrimethyl-silane, followed by desilylation: ethynyltrimethylsilane

o

R2,

(D₂

or KF, dioxane

Hal is chlorine, bromine or D is either D3 or D7

iodine, or a pseudohalogen GRN is ethynyl such as triflate

Typical desilylation conditions may be found, for example, in N. Fujii et al., J. Org. Chem. 74, 7052-58 (2009); B. Wen et al., Org. Lett. 13, 168-171 (201 1 ); or P. Wessig et al., J. Org. Chem. 69, 7582-7591 (2004). one of

Hal is chlorine, bromine or M is B, Sn, Mg, Zn, etc.. T_A is C_1.4alkyl, C_1.4haloalkyl, iodine, or a pseudohalogen together with ligands and/or halogen or cyano

such as triflate substituents Compounds of the formula I , wherein either R⁴ or R⁵ is phenyl or substituted phenyl, may be prepared by reacting a corresponding halogen precursor of the formula Id, wherein Hal is chlorine, bromine, iodine or a pseudohalogen such as Ci_-4fluoroalkylsulfonate, especially triflate, with an appropriate organometallic phenyl species of the formula XVI I I , wherein T_A is Ci_-4alkyl, Ci_-4fluoroalkyl, halogen or cyano and M is for example B, Sn, Si, Mg or Zn holding further ligands and/or substituents, by means of a transition metal-catalyzed reaction. The organometallic species of the formula XVIII is for example an aryl boronic acid T_A-Phenyl-B(OH)₂, or a suitable salt or ester thereof, which will react with a compound of the formula Id under palladium- or nickel-catalyzed conditions, such as for example the Suzuki-Miyaura conditions. A variety of metals, catalysts and ligands may be used in this reaction type. Reaction conditions and catalytic systems for such a transformation have been described, for example, in WO 2008/071405. A, G and R are as defined herein.

M is B, Sn, Mg, Zn, etc.. Hal is chlorine, bromine or T_A is C₁_₄alkyl, C^haloalkyl, together with ligands and/or iodine, or a pseudohalogen halogen or cyano

substituents such as triflate

One person skilled in the art will recognize that the polarity at the two reacting centers in this cross-coupling process may be reversed. Compounds of the formula I , wherein either R⁴ or R⁵ is phenyl or substituted phenyl, may be also prepared by reacting a corresponding organometallic species of the formula le, wherein M is for example B, Sn, Si, Mg or Zn holding further ligands and/or substituents, with an aryl halide of the formula XIX, wherein Hal is chlorine, bromine, iodine or a pseudohalogen such as Ci_-4fluoroalkylsulfonate, especially triflate, by means of a transition metal-catalyzed reaction and e.g. under similar conditions as described above. A, G and R are as defined herein. The sulfur oxidation state of compounds of the formula I, II, III, IV and XI, and of intermediates of the formula V, VI I and VI I I, wherein A is incorporating such a S atom, like for example when A is either NR¹ or NOR¹ wherein R¹ is Ci_-4alkylthio(Ci_-4)alkyl, may be easily adapted from the sulfide oxidation state into the sulfoxide or sulfone level by means of an oxidation reaction involving reagents such as, for example, m-chloroperbenzoic acid (MCPBA), oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite amongst many others.

The reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal

carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N- dimethylamine, Ν,Ν-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N- methylmorpholine, benzyltrimethylammonium hydroxide and 1 ,8-diazabicyclo[5.4.0]undec- 7-ene (DBU). The reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is carried out in the presence of a base, bases which are employed in excess, such as triethylamine, pyridine, N-methylmorpholine or N,N- diethylaniline, may also act as solvents or diluents.

The reaction is advantageously carried out in a temperature range from approximately - 80°C to approximately +140°C, preferably from approximately -30°C to approximately +100°C, in many cases in the range between ambient temperature and approximately +80°C.

A compound I can be converted in a manner known per se into another compound I by replacing one or more substituents of the starting compound I in the customary manner by (an)other substituent(s) according to the invention. Depending on the choice of the reaction conditions and starting materials which are suitable in each case, it is possible, for example, in one reaction step only to replace one substituent by another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same reaction step.

Salts of compounds I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.

Salts of compounds I can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.

Salts of compounds I can be converted, e.g. in a manner known per se, into other salts of compounds I, acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.

Depending on the procedure or the reaction conditions, the compounds I, which have salt- forming properties can be obtained in free form or in the form of salts.

The compounds I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.

Diastereomer mixtures or racemate mixtures of compounds I, in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography. Enantiomer mixtures, such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetyl celulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereose- lective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.

It is advantageous to isolate or synthesize in each case the biologically more effective iso- mer, for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity.

The compounds I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.

Many of the compounds according to the following Tables 1 to 333 below can be prepared substantially according to the methods described above.

The examples which follow, according to the following Tables 1 to 333 below, are intended to illustrate the invention and show preferred compounds of formula I. Table 1 : This table discloses the 75 compounds T1 .002 to T1 .220 of the formula la:

wherein R is CH₃, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined below:

Compound Ra R_b Rc R_d

No.

T1.002 Br C≡CH H H

T1.004 CI C≡CH H H

T1.009 CH₃ C≡CH H H

T1.010 CH₃ C≡CCH₃ H H

T1.012 CH₃CH₂ C≡CH H H

T1.014 CH₃O C≡CH H H

T1.019 CH=CH₂ C≡CH H H

T1.021 C≡CH Br H H

T1.022 C≡CH CI H H

T1.023 C≡CH CH₃ H H

T1.024 C≡CH CH=CH₂ H H

T1.025 C≡CH C≡CH H H

T1.026 C≡CH 4-CI-C₆H₄ H H

T1.028 Br H C≡CH H

T1.030 CI H C≡CH H Compound Ra Rc R_d No.

T1.035 CH₃ H C≡CH H

T1.036 CH₃ H C≡CCH₃ H

T1.038 CH₃CH₂ H C≡CH H

T1.040 CH₃O H C≡CH H

T1.042 CH=CH₂ H C≡CH H

T1.043 C≡CH H C≡CH H

T1.066 C≡CH H H CH₃

T1.069 C≡CH H H 4-CI-C₆H₄

T1.071 Br C≡CH CH₃ H

T1.073 CI C≡CH CH₃ H

T1.078 CH₃ C≡CH CH₃ H

T1.079 CH₃ C≡CCH₃ CH₃ H

T1.081 CH₃CH₂ C≡CH CH₃ H

T1.083 CH₃O C≡CH CH₃ H

T1.088 CH=CH₂ C≡CH CH₃ H

T1.090 C≡CH Br CH₃ H

T1.091 C≡CH CI CH₃ H

T1.092 C≡CH CH₃ CH₃ H

T1.093 C≡CH CH=CH₂ CH₃ H

T1.094 C≡CH C≡CH CH₃ H

T1.095 C≡CH 4-CI-C₆H₄ CH₃ H

T1.097 Br C≡CH H CH₃

T1.099 CI C≡CH H CH₃

T1.104 CH₃ C≡CH H CH₃

T1.105 CH₃ C≡CCH₃ H CH₃

T1.107 CH₃CH₂ C≡CH H CH₃

T1.109 CH₃0 C≡CH H CH₃

T1.114 CH=CH₂ C≡CH H CH₃

T1.116 C≡CH Br H CH₃

T1.117 C≡CH CI H CH₃

T1.118 C≡CH CH₃ H CH₃

T1.119 C≡CH CH=CH₂ H CH₃

T1.120 C≡CH C≡CH H CH₃

T1.121 C≡CH 4-CI-C₆H₄ H CH₃

T1.123 Br CH₃ C≡CH H

T1.125 CI CH₃ C≡CH H Compound Ra R_b Rc R_d No.

T1.129 CH₃ CH₃ C≡CCH₃ H

T1.131 CH₃CH₂ CH₃ C≡CH H

T1.133 CH₃O CH₃ C≡CH H

T1.135 CH=CH₂ CH₃ C≡CH H

T1.136 C≡CH CH₃ C≡CH H

T1.138 Br H C≡CH CH₃

T1.140 CI H C≡CH CH₃

T1.145 CH₃ H C≡CH CH₃

T1.146 CH₃ H C≡CCH₃ CH₃

T1.148 CH₃CH₂ H C≡CH CH₃

T1.150 CH₃O H C≡CH CH₃

T1.155 CH=CH₂ H C≡CH CH₃

T1.156 C≡CH H Br CH₃

T1.157 C≡CH H CI CH₃

T1.158 C≡CH H CH₃ CH₃

T1.159 C≡CH H CH=CH₂ CH₃

T1.160 C≡CH H C≡CH CH₃

T1.184 C≡CH CH₃ H 4-CI-C₆H₄

T1.208 C≡CH H CH₃ 4-CI-C₆H₄

T1.210 cyclopropyl CH₃ C≡CH H

T1.211 cyclopropyl C≡CH CH₃ H

T1.212 cyclopropyl C≡CCH₃ CH₃ H

T1.215 C≡CH CH₃ CH₃ CH₃

T1.220 C≡CCH₃ CH₃ CH₃ CH₃

Table 2: This table discloses the 75 compounds T2.002 to T2.220 of the formula la, wherein R is hydrogen, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 3: This table discloses the 75 compounds T3.002 to T3.220 of the formula la, wherein R is CH₂CH₃, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 4: This table discloses the 75 compounds T4.002 to T4.220 of the formula la, wherein R is CH₂CF₃, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 5: This table discloses the 75 compounds T5.002 to T5.220 of the formula la, wherein R is CH₂OCH₃, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 6: This table discloses the 75 compounds T6.002 to T6.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 7: This table discloses the 75 compounds T7.002 to T7.220 of the formula la, wherein R is allyl, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 8: This table discloses the 75 compounds T8.002 to T8.220 of the formula la, wherein R is propargyl, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 9: This table discloses the 75 compounds T9.002 to T9.220 of the formula la, wherein R is benzyl, A is NH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 10: This table discloses the 75 compounds T10.002 to T10.220 of the formula la, wherein R is CH₃, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 1 : This table discloses the 75 compounds T1 1 .002 to T1 1 .220 of the formula la, wherein R is hydrogen, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 12: This table discloses the 75 compounds T12.002 to T12.220 of the formula la, wherein R is CH₂CH₃, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 13: This table discloses the 75 compounds T13.002 to T13.220 of the formula la, wherein R is CH₂CF₃, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 14: This table discloses the 75 compounds T14.002 to T14.220 of the formula la, wherein R is CH₂OCH₃, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 15: This table discloses the 75 compounds T15.002 to T15.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 16: This table discloses the 75 compounds T16.002 to T16.220 of the formula la, wherein R is allyl, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 17: This table discloses the 75 compounds T17.002 to T17.220 of the formula la, wherein R is propargyl, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 18: This table discloses the 75 compounds T18.002 to T18.220 of the formula la, wherein R is benzyl, A is NCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 19: This table discloses the 75 compounds T19.002 to T19.220 of the formula la, wherein R is CH₃, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 20: This table discloses the 75 compounds T20.002 to T20.220 of the formula la, wherein R is hydrogen, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 21 : This table discloses the 75 compounds T21 .002 to T21 .220 of the formula la, wherein R is CH₂CH₃, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 22: This table discloses the 75 compounds T22.002 to T22.220 of the formula la, wherein R is CH₂CF₃, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 23: This table discloses the 75 compounds T23.002 to T23.220 of the formula la, wherein R is CH₂OCH₃, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 24: This table discloses the 75 compounds T24.002 to T24.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 25: This table discloses the 75 compounds T25.002 to T25.220 of the formula la, wherein R is allyl, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 26: This table discloses the 75 compounds T26.002 to T26.220 of the formula la, wherein R is propargyl, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 27: This table discloses the 75 compounds T27.002 to T27.220 of the formula la, wherein R is benzyl, A is NCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 28: This table discloses the 75 compounds T28.002 to T28.220 of the formula la, wherein R is CH₃, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 29: This table discloses the 75 compounds T29.002 to T29.220 of the formula la, wherein R is hydrogen, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 30: This table discloses the 75 compounds T30.002 to T30.220 of the formula la, wherein R is CH₂CH₃, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 31 : This table discloses the 75 compounds T31 .002 to T31 .220 of the formula la, wherein R is CH₂CF₃, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 32: This table discloses the 75 compounds T32.002 to T32.220 of the formula la, wherein R is CH₂OCH₃, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 33: This table discloses the 75 compounds T33.002 to T33.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 34: This table discloses the 75 compounds T34.002 to T34.220 of the formula la, wherein R is allyl, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 35: This table discloses the 75 compounds T35.002 to T35.220 of the formula la, wherein R is propargyl, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 36: This table discloses the 75 compounds T36.002 to T36.220 of the formula la, wherein R is benzyl, A is NCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 37: This table discloses the 75 compounds T37.002 to T37.220 of the formula la, wherein R is CH₃, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 38: This table discloses the 75 compounds T38.002 to T38.220 of the formula la, wherein R is hydrogen, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 39: This table discloses the 75 compounds T39.002 to T39.220 of the formula la, wherein R is CH₂CH₃, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 40: This table discloses the 75 compounds T40.002 to T40.220 of the formula la, wherein R is CH₂CF₃, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 41 : This table discloses the 75 compounds T41 .002 to T41 .220 of the formula la, wherein R is CH₂OCH₃, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 42: This table discloses the 75 compounds T42.002 to T42.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 43: This table discloses the 75 compounds T43.002 to T43.220 of the formula la, wherein R is allyl, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 44: This table discloses the 75 compounds T44.002 to T44.220 of the formula la, wherein R is propargyl, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 45: This table discloses the 75 compounds T45.002 to T45.220 of the formula la, wherein R is benzyl, A is N-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 46: This table discloses the 75 compounds T46.002 to T46.220 of the formula la, wherein R is CH₃, A is NCH₂CH=CH2, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 47: This table discloses the 75 compounds T47.002 to T47.220 of the formula la, wherein R is hydrogen, A is NCH₂CH=CH2, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 48: This table discloses the 75 compounds T48.002 to T48.220 of the formula la, wherein R is CH₂CH₃, A is NCH₂CH=CH2, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 49: This table discloses the 75 compounds T49.002 to T49.220 of the formula la, wherein R is CH₂CF₃, A is NCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 50: This table discloses the 75 compounds T50.002 to T50.220 of the formula la, wherein R is CH₂OCH₃, A is NCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 51 : This table discloses the 75 compounds T51 .002 to T51 .220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 52: This table discloses the 75 compounds T52.002 to T52.220 of the formula la, wherein R is allyl, A is NCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 53: This table discloses the 75 compounds T53.002 to T53.220 of the formula la, wherein R is propargyl, A is NCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 54: This table discloses the 75 compounds T54.002 to T54.220 of the formula la, wherein R is benzyl, A is NCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 55: This table discloses the 75 compounds T55.002 to T55.220 of the formula la, wherein R is CH₃, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 56: This table discloses the 75 compounds T56.002 to T56.220 of the formula la, wherein R is hydrogen, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 57: This table discloses the 75 compounds T57.002 to T57.220 of the formula la, wherein R is CH₂CH₃, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 58: This table discloses the 75 compounds T58.002 to T58.220 of the formula la, wherein R is CH₂CF₃, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 59: This table discloses the 75 compounds T59.002 to T59.220 of the formula la, wherein R is CH₂OCH₃, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 60: This table discloses the 75 compounds T60.002 to T60.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 61 : This table discloses the 75 compounds T61 .002 to T61 .220 of the formula la, wherein R is allyl, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 62: This table discloses the 75 compounds T62.002 to T62.220 of the formula la, wherein R is propargyl, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 63: This table discloses the 75 compounds T63.002 to T63.220 of the formula la, wherein R is benzyl, A is NCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 64: This table discloses the 75 compounds T64.002 to T64.220 of the formula la, wherein R is CH₃, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1. Table 65: This table discloses the 75 compounds T65.002 to T65.220 of the formula la, wherein R is hydrogen, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 66: This table discloses the 75 compounds T66.002 to T66.220 of the formula la, wherein R is CH₂CH₃, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 67: This table discloses the 75 compounds T67.002 to T67.220 of the formula la, wherein R is CH₂CF₃, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 68: This table discloses the 75 compounds T68.002 to T68.220 of the formula la, wherein R is CH₂OCH₃, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 69: This table discloses the 75 compounds T69.002 to T69.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 70: This table discloses the 75 compounds T70.002 to T70.220 of the formula la, wherein R is allyl, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 71 : This table discloses the 75 compounds T71 .002 to T71 .220 of the formula la, wherein R is propargyl, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 72: This table discloses the 75 compounds T72.002 to T72.220 of the formula la, wherein R is benzyl, A is NCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 73: This table discloses the 75 compounds T73.002 to T73.220 of the formula la, wherein R is CH₃, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 74: This table discloses the 75 compounds T74.002 to T74.220 of the formula la, wherein R is hydrogen, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 75: This table discloses the 75 compounds T75.002 to T75.220 of the formula la, wherein R is CH₂CH₃, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 76: This table discloses the 75 compounds T76.002 to T76.220 of the formula la, wherein R is CH₂CF₃, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 77: This table discloses the 75 compounds T77.002 to T77.220 of the formula la, wherein R is CH₂OCH₃, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 78: This table discloses the 75 compounds T78.002 to T78.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 79: This table discloses the 75 compounds T79.002 to T79.220 of the formula la, wherein R is allyl, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 80: This table discloses the 75 compounds T80.002 to T80.220 of the formula la, wherein R is propargyl, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 81 : This table discloses the 75 compounds T81 .002 to T81 .220 of the formula la, wherein R is benzyl, A is NCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 82: This table discloses the 75 compounds T82.002 to T82.220 of the formula la, wherein R is CH₃, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 83: This table discloses the 75 compounds T83.002 to T83.220 of the formula la, wherein R is hydrogen, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 84: This table discloses the 75 compounds T84.002 to T84.220 of the formula la, wherein R is CH₂CH₃, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 85: This table discloses the 75 compounds T85.002 to T85.220 of the formula la, wherein R is CH₂CF₃, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 86: This table discloses the 75 compounds T86.002 to T86.220 of the formula la, wherein R is CH₂OCH₃, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 87: This table discloses the 75 compounds T87.002 to T87.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 88: This table discloses the 75 compounds T88.002 to T88.220 of the formula la, wherein R is allyl, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 89: This table discloses the 75 compounds T89.002 to T89.220 of the formula la, wherein R is propargyl, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 90: This table discloses the 75 compounds T90.002 to T90.220 of the formula la, wherein R is benzyl, A is NCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 91 : This table discloses the 75 compounds T91 .002 to T91 .220 of the formula la, wherein R is CH₃, A is NCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 92: This table discloses the 75 compounds T92.002 to T92.220 of the formula la, wherein R is hydrogen, A is NCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 93: This table discloses the 75 compounds T93.002 to T93.220 of the formula la, wherein R is CH₂CH₃, A is NCH2CH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 94: This table discloses the 75 compounds T94.002 to T94.220 of the formula la, wherein R is CH₂CF₃, A is NCH2CH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 95: This table discloses the 75 compounds T95.002 to T95.220 of the formula la, wherein R is CH₂OCH₃, A is NCH2CH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 96: This table discloses the 75 compounds T96.002 to T96.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 97: This table discloses the 75 compounds T97.002 to T97.220 of the formula la, wherein R is allyl, A is NCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 98: This table discloses the 75 compounds T98.002 to T98.220 of the formula la, wherein R is propargyl, A is NCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 99: This table discloses the 75 compounds T99.002 to T99.220 of the formula la, wherein R is benzyl, A is NCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 100: This table discloses the 75 compounds T100.002 to T100.220 of the formula la, wherein R is CH₃, A is NCH2OCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 101 : This table discloses the 75 compounds T101 .002 to T101 .220 of the formula la, wherein R is hydrogen, A is NCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 102: This table discloses the 75 compounds T102.002 to T102.220 of the formula la, wherein R is CH₂CH₃, A is NCH2OCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 103: This table discloses the 75 compounds T103.002 to T103.220 of the formula la, wherein R is CH₂CF₃, A is NCH2OCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 104: This table discloses the 75 compounds T104.002 to T104.220 of the formula la, wherein R is CH₂OCH₃, A is NCH2OCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 105: This table discloses the 75 compounds T105.002 to T105.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 106: This table discloses the 75 compounds T106.002 to T106.220 of the formula la, wherein R is allyl, A is NCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 107: This table discloses the 75 compounds T107.002 to T107.220 of the formula la, wherein R is propargyl, A is NCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 108: This table discloses the 75 compounds T108.002 to T108.220 of the formula la, wherein R is benzyl, A is NCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 109: This table discloses the 75 compounds T109.002 to T109.220 of the formula la, wherein R is CH₃, A is NCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 10: This table discloses the 75 compounds T1 10.002 to T1 10.220 of the formula la, wherein R is hydrogen, A is NCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 1 1 : This table discloses the 75 compounds T1 1 1 .002 to T1 1 1 .220 of the formula la, wherein R is CH₂CH₃, A is NCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 12: This table discloses the 75 compounds T1 12.002 to T1 12.220 of the formula la, wherein R is CH₂CF₃, A is NCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 13: This table discloses the 75 compounds T1 13.002 to T1 13.220 of the formula la, wherein R is CH₂OCH₃, A is NCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 1 14: This table discloses the 75 compounds T1 14.002 to T1 14.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 1 15: This table discloses the 75 compounds T1 15.002 to T1 15.220 of the formula la, wherein R is allyl, A is NCH₂CH₂OCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 1 16: This table discloses the 75 compounds T1 16.002 to T1 16.220 of the formula la, wherein R is propargyl, A is NCH₂CH₂OCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 17: This table discloses the 75 compounds T1 17.002 to T1 17.220 of the formula la, wherein R is benzyl, A is NCH₂CH₂OCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 18: This table discloses the 75 compounds T1 18.002 to T1 18.220 of the formula la, wherein R is CH₃, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 1 19: This table discloses the 75 compounds T1 19.002 to T1 19.220 of the formula la, wherein R is hydrogen, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 120: This table discloses the 75 compounds T120.002 to T120.220 of the formula la, wherein R is CH₂CH₃, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 121 : This table discloses the 75 compounds T121 .002 to T121 .220 of the formula la, wherein R is CH₂CF₃, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 122: This table discloses the 75 compounds T122.002 to T122.220 of the formula la, wherein R is CH₂OCH₃, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 123: This table discloses the 75 compounds T123.002 to T123.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 124: This table discloses the 75 compounds T124.002 to T124.220 of the formula la, wherein R is allyl, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 125: This table discloses the 75 compounds T125.002 to T125.220 of the formula la, wherein R is propargyl, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 126: This table discloses the 75 compounds T126.002 to T126.220 of the formula la, wherein R is benzyl, A is NOH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 127: This table discloses the 75 compounds T127.002 to T127.220 of the formula la, wherein R is CH₃, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 128: This table discloses the 75 compounds T128.002 to T128.220 of the formula la, wherein R is hydrogen, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 129: This table discloses the 75 compounds T129.002 to T129.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 130: This table discloses the 75 compounds T130.002 to T130.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 131 : This table discloses the 75 compounds T131 .002 to T131 .220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 132: This table discloses the 75 compounds T132.002 to T132.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 133: This table discloses the 75 compounds T133.002 to T133.220 of the formula la, wherein R is allyl, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 134: This table discloses the 75 compounds T134.002 to T134.220 of the formula la, wherein R is propargyl, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 135: This table discloses the 75 compounds T135.002 to T135.220 of the formula la, wherein R is benzyl, A is NOCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 136: This table discloses the 75 compounds T136.002 to T136.220 of the formula la, wherein R is CH₃, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 137: This table discloses the 75 compounds T137.002 to T137.220 of the formula la, wherein R is hydrogen, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 138: This table discloses the 75 compounds T138.002 to T138.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 139: This table discloses the 75 compounds T139.002 to T139.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 140: This table discloses the 75 compounds T140.002 to T140.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 141 : This table discloses the 75 compounds T141 .002 to T141 .220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 142: This table discloses the 75 compounds T142.002 to T142.220 of the formula la, wherein R is allyl, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 143: This table discloses the 75 compounds T143.002 to T143.220 of the formula la, wherein R is propargyl, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 144: This table discloses the 75 compounds T144.002 to T144.220 of the formula la, wherein R is benzyl, A is NOCH₂CH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 145: This table discloses the 75 compounds T145.002 to T145.220 of the formula la, wherein R is CH₃, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 146: This table discloses the 75 compounds T146.002 to T146.220 of the formula la, wherein R is hydrogen, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 147: This table discloses the 75 compounds T147.002 to T147.220 of the formula la, wherein R is CH₂CH₃, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 148: This table discloses the 75 compounds T148.002 to T148.220 of the formula la, wherein R is CH₂CF₃, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 149: This table discloses the 75 compounds T149.002 to T149.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 150: This table discloses the 75 compounds T150.002 to T150.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 151 : This table discloses the 75 compounds T151 .002 to T151 .220 of the formula la, wherein R is allyl, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 152: This table discloses the 75 compounds T152.002 to T152.220 of the formula la, wherein R is propargyl, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 153: This table discloses the 75 compounds T153.002 to T153.220 of the formula la, wherein R is benzyl, A is NOCH(CH₃)₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 154: This table discloses the 75 compounds T154.002 to T154.220 of the formula la, wherein R is CH₃, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 155: This table discloses the 75 compounds T155.002 to T155.220 of the formula la, wherein R is hydrogen, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 156: This table discloses the 75 compounds T156.002 to T156.220 of the formula la, wherein R is CH₂CH₃, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 157: This table discloses the 75 compounds T157.002 to T157.220 of the formula la, wherein R is CH₂CF₃, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 158: This table discloses the 75 compounds T158.002 to T158.220 of the formula la, wherein R is CH₂OCH₃, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 159: This table discloses the 75 compounds T159.002 to T159.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 160: This table discloses the 75 compounds T160.002 to T160.220 of the formula la, wherein R is allyl, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 161 : This table discloses the 75 compounds T161 .002 to T161 .220 of the formula la, wherein R is propargyl, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 162: This table discloses the 75 compounds T162.002 to T162.220 of the formula la, wherein R is benzyl, A is NO-cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 163: This table discloses the 75 compounds T163.002 to T163.220 of the formula la, wherein R is CH₃, A is NOCH₂CH=CH2, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 164: This table discloses the 75 compounds T164.002 to T164.220 of the formula la, wherein R is hydrogen, A is NOCH₂CH=CH2, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 165: This table discloses the 75 compounds T165.002 to T165.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 166: This table discloses the 75 compounds T166.002 to T166.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₂CH=CH2, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 167: This table discloses the 75 compounds T167.002 to T167.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 168: This table discloses the 75 compounds T168.002 to T168.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 169: This table discloses the 75 compounds T169.002 to T169.220 of the formula la, wherein R is allyl, A is NOCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 170: This table discloses the 75 compounds T170.002 to T170.220 of the formula la, wherein R is propargyl, A is NOCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 171 : This table discloses the 75 compounds T171 .002 to T171 .220 of the formula la, wherein R is benzyl, A is NOCH₂CH=CH₂, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 172: This table discloses the 75 compounds T172.002 to T172.220 of the formula la, wherein R is CH₃, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 173: This table discloses the 75 compounds T173.002 to T173.220 of the formula la, wherein R is hydrogen, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 174: This table discloses the 75 compounds T174.002 to T174.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 175: This table discloses the 75 compounds T175.002 to T175.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 176: This table discloses the 75 compounds T176.002 to T176.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 177: This table discloses the 75 compounds T177.002 to T177.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 178: This table discloses the 75 compounds T178.002 to T178.220 of the formula la, wherein R is allyl, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 179: This table discloses the 75 compounds T179.002 to T179.220 of the formula la, wherein R is propargyl, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 180: This table discloses the 75 compounds T180.002 to T180.220 of the formula la, wherein R is benzyl, A is NOCH₂C≡CH, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 181 : This table discloses the 75 compounds T181 .002 to T181 .220 of the formula la, wherein R is CH₃, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 182: This table discloses the 75 compounds T182.002 to T182.220 of the formula la, wherein R is hydrogen, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 183: This table discloses the 75 compounds T183.002 to T183.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 184: This table discloses the 75 compounds T184.002 to T184.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 185: This table discloses the 75 compounds T185.002 to T185.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 186: This table discloses the 75 compounds T186.002 to T186.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 187: This table discloses the 75 compounds T187.002 to T187.220 of the formula la, wherein R is allyl, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 188: This table discloses the 75 compounds T188.002 to T188.220 of the formula la, wherein R is propargyl, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 189: This table discloses the 75 compounds T189.002 to T189.220 of the formula la, wherein R is benzyl, A is NOCH₂cyclopropyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 190: This table discloses the 75 compounds T190.002 to T190.220 of the formula la, wherein R is CH₃, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 191 : This table discloses the 75 compounds T191 .002 to T191 .220 of the formula la, wherein R is hydrogen, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 192: This table discloses the 75 compounds T192.002 to T192.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 193: This table discloses the 75 compounds T193.002 to T193.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 194: This table discloses the 75 compounds T194.002 to T194.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 195: This table discloses the 75 compounds T195.002 to T195.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 196: This table discloses the 75 compounds T196.002 to T196.220 of the formula la, wherein R is allyl, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 197: This table discloses the 75 compounds T197.002 to T197.220 of the formula la, wherein R is propargyl, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 198: This table discloses the 75 compounds T198.002 to T198.220 of the formula la, wherein R is benzyl, A is NOCH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 199: This table discloses the 75 compounds T199.002 to T199.220 of the formula la, wherein R is CH₃, A is NOCH₂CH₂OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 200: This table discloses the 75 compounds T200.002 to T200.220 of the formula la, wherein R is hydrogen, A is NOCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 201 : This table discloses the 75 compounds T201 .002 to T201 .220 of the formula la, wherein R is CH₂CH₃, A is NOCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 202: This table discloses the 75 compounds T202.002 to T202.220 of the formula la, wherein R is CH₂CF₃, A is NOCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 203: This table discloses the 75 compounds T203.002 to T203.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 204: This table discloses the 75 compounds T204.002 to T204.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 205: This table discloses the 75 compounds T205.002 to T205.220 of the formula la, wherein R is allyl, A is NOCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 206: This table discloses the 75 compounds T206.002 to T206.220 of the formula la, wherein R is propargyl, A is NOCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 207: This table discloses the 75 compounds T207.002 to T207.220 of the formula la, wherein R is benzyl, A is NOCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 208: This table discloses the 75 compounds T208.002 to T208.220 of the formula la, wherein R is CH₃, A is NOCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 209: This table discloses the 75 compounds T209.002 to T209.220 of the formula la, wherein R is hydrogen, A is NOCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 210: This table discloses the 75 compounds T210.002 to T210.220 of the formula la, wherein R is CH₂CH₃, A is NOCH2CH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 21 1 : This table discloses the 75 compounds T21 1 .002 to T21 1 .220 of the formula la, wherein R is CH₂CF₃, A is NOCH2CH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 212: This table discloses the 75 compounds T212.002 to T212.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH2CH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 213: This table discloses the 75 compounds T213.002 to T213.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 214: This table discloses the 75 compounds T214.002 to T214.220 of the formula la, wherein R is allyl, A is NOCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 215: This table discloses the 75 compounds T215.002 to T215.220 of the formula la, wherein R is propargyl, A is NOCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 216: This table discloses the 75 compounds T216.002 to T216.220 of the formula la, wherein R is benzyl, A is NOCH2CH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 217: This table discloses the 75 compounds T217.002 to T217.220 of the formula la, wherein R is CH₃, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 218: This table discloses the 75 compounds T218.002 to T218.220 of the formula la, wherein R is hydrogen, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 219: This table discloses the 75 compounds T219.002 to T219.220 of the formula la, wherein R is CH₂CH₃, A is NOCH2OCH2CH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 220: This table discloses the 75 compounds T220.002 to T220.220 of the formula la, wherein R is CH₂CF₃, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 221 : This table discloses the 75 compounds T221 .002 to T221 .220 of the formula la, wherein R is CH₂OCH₃, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 222: This table discloses the 75 compounds T222.002 to T222.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 223: This table discloses the 75 compounds T223.002 to T223.220 of the formula la, wherein R is allyl, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 224: This table discloses the 75 compounds T224.002 to T224.220 of the formula la, wherein R is propargyl, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 225: This table discloses the 75 compounds T225.002 to T225.220 of the formula la, wherein R is benzyl, A is NOCH2OCH2CH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 226: This table discloses the 75 compounds T226.002 to T226.220 of the formula la, wherein R is CH₃, A is NOCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 227: This table discloses the 75 compounds T227.002 to T227.220 of the formula la, wherein R is hydrogen, A is NOCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 228: This table discloses the 75 compounds T228.002 to T228.220 of the formula la, wherein R is CH₂CH₃, A is NOCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 229: This table discloses the 75 compounds T229.002 to T229.220 of the formula la, wherein R is CH₂CF₃, A is NOCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 230: This table discloses the 75 compounds T230.002 to T230.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 231 : This table discloses the 75 compounds T231 .002 to T231 .220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 232: This table discloses the 75 compounds T232.002 to T232.220 of the formula la, wherein R is allyl, A is NOCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 233: This table discloses the 75 compounds T233.002 to T233.220 of the formula la, wherein R is propargyl, A is NOCH2CH2OCH2OCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 234: This table discloses the 75 compounds T234.002 to T234.220 of the formula la, wherein R is benzyl, A is NOCH2CH2OCH2OCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 235: This table discloses the 75 compounds T235.002 to T235.220 of the formula la, wherein R is CH₃, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 236: This table discloses the 75 compounds T236.002 to T236.220 of the formula la, wherein R is hydrogen, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 237: This table discloses the 75 compounds T237.002 to T237.220 of the formula la, wherein R is CH₂CH₃, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 238: This table discloses the 75 compounds T238.002 to T238.220 of the formula la, wherein R is CH₂CF₃, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 239: This table discloses the 75 compounds T239.002 to T239.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 240: This table discloses the 75 compounds T240.002 to T240.220 of the formula la, wherein R is CH₂CH₂OCI-l₃, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 241 : This table discloses the 75 compounds T241 .002 to T241 .220 of the formula la, wherein R is allyl, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 242: This table discloses the 75 compounds T242.002 to T242.220 of the formula la, wherein R is propargyl, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 243: This table discloses the 75 compounds T243.002 to T243.220 of the formula la, wherein R is benzyl, A is NOCH₂-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 244: This table discloses the 75 compounds T244.002 to T244.220 of the formula la, wherein R is CH₃, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 245: This table discloses the 75 compounds T245.002 to T245.220 of the formula la, wherein R is hydrogen, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 246: This table discloses the 75 compounds T246.002 to T246.220 of the formula la, wherein R is CH₂CH₃, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 247: This table discloses the 75 compounds T247.002 to T247.220 of the formula la, wherein R is CH₂CF₃, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 248: This table discloses the 75 compounds T248.002 to T248.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 249: This table discloses the 75 compounds T249.002 to T249.220 of the formula la, wherein R is CH₂CH₂OCI-l₃, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 250: This table discloses the 75 compounds T250.002 to T250.220 of the formula la, wherein R is allyl, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 251 : This table discloses the 75 compounds T251 .002 to T251 .220 of the formula la, wherein R is propargyl, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 252: This table discloses the 75 compounds T252.002 to T252.220 of the formula la, wherein R is benzyl, A is NO-(tetrahydrofuran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 253: This table discloses the 75 compounds T253.002 to T253.220 of the formula la, wherein R is CH₃, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 254: This table discloses the 75 compounds T254.002 to T254.220 of the formula la, wherein R is hydrogen, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 255: This table discloses the 75 compounds T255.002 to T255.220 of the formula la, wherein R is CH₂CH₃, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 256: This table discloses the 75 compounds T256.002 to T256.220 of the formula la, wherein R is CH₂CF₃, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 257: This table discloses the 75 compounds T257.002 to T257.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 258: This table discloses the 75 compounds T258.002 to T258.220 of the formula la, wherein R is CH₂CH₂OCI-l₃, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 259: This table discloses the 75 compounds T259.002 to T259.220 of the formula la, wherein R is allyl, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 260: This table discloses the 75 compounds T260.002 to T260.220 of the formula la, wherein R is propargyl, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 261 : This table discloses the 75 compounds T261 .002 to T261 .220 of the formula la, wherein R is benzyl, A is NO-(tetrahydropyran-2-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 262: This table discloses the 75 compounds T262.002 to T262.220 of the formula la, wherein R is CH₃, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 263: This table discloses the 75 compounds T263.002 to T263.220 of the formula la, wherein R is hydrogen, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 264: This table discloses the 75 compounds T264.002 to T264.220 of the formula la, wherein R is CH₂CH₃, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 265: This table discloses the 75 compounds T265.002 to T265.220 of the formula la, wherein R is CH₂CF₃, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 266: This table discloses the 75 compounds T266.002 to T266.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 267: This table discloses the 75 compounds T267.002 to T267.220 of the formula la, wherein R is CH₂CH₂OCI-l₃, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 268: This table discloses the 75 compounds T268.002 to T268.220 of the formula la, wherein R is allyl, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 269: This table discloses the 75 compounds T269.002 to T269.220 of the formula la, wherein R is propargyl, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 270: This table discloses the 75 compounds T270.002 to T270.220 of the formula la, wherein R is benzyl, A is NO-(tetrahydropyran-4-yl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 271 : This table discloses the 75 compounds T271 .002 to T271 .220 of the formula la, wherein R is CH₃, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 272: This table discloses the 75 compounds T272.002 to T272.220 of the formula la, wherein R is hydrogen, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 273: This table discloses the 75 compounds T273.002 to T273.220 of the formula la, wherein R is CH₂CH₃, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 274: This table discloses the 75 compounds T274.002 to T274.220 of the formula la, wherein R is CH₂CF₃, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 275: This table discloses the 75 compounds T275.002 to T275.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 276: This table discloses the 75 compounds T276.002 to T276.220 of the formula la, wherein R is CH₂CH₂OCI-l₃, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 277: This table discloses the 75 compounds T277.002 to T277.220 of the formula la, wherein R is allyl, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 278: This table discloses the 75 compounds T278.002 to T278.220 of the formula la, wherein R is propargyl, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 279: This table discloses the 75 compounds T279.002 to T279.220 of the formula la, wherein R is benzyl, A is NO-(tetrahydrofuran-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 280: This table discloses the 75 compounds T280.002 to T280.220 of the formula la, wherein R is CH₃, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 281 : This table discloses the 75 compounds T281 .002 to T281 .220 of the formula la, wherein R is hydrogen, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 282: This table discloses the 75 compounds T282.002 to T282.220 of the formula la, wherein R is CH₂CH₃, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 283: This table discloses the 75 compounds T283.002 to T283.220 of the formula la, wherein R is CH₂CF₃, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 284: This table discloses the 75 compounds T284.002 to T284.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 285: This table discloses the 75 compounds T285.002 to T285.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 286: This table discloses the 75 compounds T286.002 to T286.220 of the formula la, wherein R is allyl, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 287: This table discloses the 75 compounds T287.002 to T287.220 of the formula la, wherein R is propargyl, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 288: This table discloses the 75 compounds T288.002 to T288.220 of the formula la, wherein R is benzyl, A is NO-(tetrahydrofuran-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1.

Table 289: This table discloses the 75 compounds T289.002 to T289.220 of the formula la, wherein R is CH₃, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 290: This table discloses the 75 compounds T290.002 to T290.220 of the formula la, wherein R is hydrogen, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 291 : This table discloses the 75 compounds T291 .002 to T291 .220 of the formula la, wherein R is CH₂CH₃, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 292: This table discloses the 75 compounds T292.002 to T292.220 of the formula la, wherein R is CH₂CF₃, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 293: This table discloses the 75 compounds T293.002 to T293.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 294: This table discloses the 75 compounds T294.002 to T294.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 295: This table discloses the 75 compounds T295.002 to T295.220 of the formula la, wherein R is allyl, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 296: This table discloses the 75 compounds T296.002 to T296.220 of the formula la, wherein R is propargyl, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 297: This table discloses the 75 compounds T297.002 to T297.220 of the formula la, wherein R is benzyl, A is NO-(tetrahydropyran-4-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 298: This table discloses the 75 compounds T298.002 to T298.220 of the formula la, wherein R is CH₃, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 299: This table discloses the 75 compounds T299.002 to T299.220 of the formula la, wherein R is hydrogen, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 300: This table discloses the 75 compounds T300.002 to T300.220 of the formula la, wherein R is CH₂CH₃, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 301 : This table discloses the 75 compounds T301 .002 to T301 .220 of the formula la, wherein R is CH₂CF₃, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 302: This table discloses the 75 compounds T302.002 to T302.220 of the formula la, wherein R is CH₂OCH₃, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 303: This table discloses the 75 compounds T303.002 to T303.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 304: This table discloses the 75 compounds T304.002 to T304.220 of the formula la, wherein R is allyl, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 305: This table discloses the 75 compounds T305.002 to T305.220 of the formula la, wherein R is propargyl, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 306: This table discloses the 75 compounds T306.002 to T306.220 of the formula la, wherein R is benzyl, A is NO-cyclohexyl, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 307: This table discloses the 75 compounds T307.002 to T307.220 of the formula la, wherein R is CH₃, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 308: This table discloses the 75 compounds T308.002 to T308.220 of the formula la, wherein R is hydrogen, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 309: This table discloses the 75 compounds T309.002 to T309.220 of the formula la, wherein R is CH₂CH₃, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 310: This table discloses the 75 compounds T310.002 to T310.220 of the formula la, wherein R is CH₂CF₃, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 31 1 : This table discloses the 75 compounds T31 1 .002 to T31 1 .220 of the formula la, wherein R is CH₂OCH₃, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 312: This table discloses the 75 compounds T312.002 to T312.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 313: This table discloses the 75 compounds T313.002 to T313.220 of the formula la, wherein R is allyl, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 314: This table discloses the 75 compounds T314.002 to T314.220 of the formula la, wherein R is propargyl, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 315: This table discloses the 75 compounds T315.002 to T315.220 of the formula la, wherein R is benzyl, A is NO-(furan-2-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 316: This table discloses the 75 compounds T316.002 to T316.220 of the formula la, wherein R is CH₃, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 317: This table discloses the 75 compounds T317.002 to T317.220 of the formula la, wherein R is hydrogen, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 318: This table discloses the 75 compounds T318.002 to T318.220 of the formula la, wherein R is CH₂CH₃, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 319: This table discloses the 75 compounds T319.002 to T319.220 of the formula la, wherein R is CH₂CF₃, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 320: This table discloses the 75 compounds T320.002 to T320.220 of the formula la, wherein R is CH₂OCH₃, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 321 : This table discloses the 75 compounds T321 .002 to T321 .220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 322: This table discloses the 75 compounds T322.002 to T322.220 of the formula la, wherein R is allyl, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 323: This table discloses the 75 compounds T323.002 to T323.220 of the formula la, wherein R is propargyl, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 324: This table discloses the 75 compounds T324.002 to T324.220 of the formula la, wherein R is benzyl, A is NO-(furan-3-ylmethyl), G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 325: This table discloses the 75 compounds T325.002 to T325.220 of the formula la, wherein R is CH₃, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 326: This table discloses the 75 compounds T326.002 to T326.220 of the formula la, wherein R is hydrogen, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 327: This table discloses the 75 compounds T327.002 to T327.220 of the formula la, wherein R is CH₂CH₃, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 328: This table discloses the 75 compounds T328.002 to T328.220 of the formula la, wherein R is CH₂CF₃, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 329: This table discloses the 75 compounds T329.002 to T329.220 of the formula la, wherein R is CH₂OCH₃, A is NOCH2CH2SCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 . Table 330: This table discloses the 75 compounds T330.002 to T330.220 of the formula la, wherein R is CH₂CH₂OCH₃, A is NOCH2CH2SCH3, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 331 : This table discloses the 75 compounds T331 .002 to T331 .220 of the formula la, wherein R is allyl, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 332: This table discloses the 75 compounds T332.002 to T332.220 of the formula la, wherein R is propargyl, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Table 333: This table discloses the 75 compounds T333.002 to T333.220 of the formula la, wherein R is benzyl, A is NOCH2CH2SCH₃, G is hydrogen and R_a, R_b, R_c and R_d are as defined in Table 1 .

Herbicidal uses - crops of useful plants, weeds, application rates, et al.

In all aspects of the invention (e.g. the methods of use of the invention), crops of useful plants, e.g. in which the compounds or compositions according to the invention can be used, comprise (e.g. are), in particular, cereals (e.g. non-oat cereals, in particular wheat, barley, rye and/or triticale), rice, corn (maize), sugarcane, soybean, cotton, rape (e.g. oilseed rape or canola), sunflower, sugarbeet, peanut and/or plantation crops. Preferably, in all aspects of the invention, the crops of useful plants, e.g. in which the compounds or compositions according to the invention can be used, comprise (e.g. are) cereals (e.g. non-oat cereals, in particular wheat, barley, rye and/or triticale), rice, corn (maize), sugarcane, soybean, cotton, rape (e.g. oilseed rape or canola), sunflower and/or sugarbeet; more preferably, cereals (e.g. non-oat cereals, in particular wheat, barley, rye and/or triticale), rice, corn (maize) and/or soybean.

The term "crops" is to be understood as including also crops that have been rendered tolerant to herbicides such as bromoxynil or dicamba or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and/or trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- or glufosinate-resistant maize varieties e.g. commercially available under the trade names RoundupReady® or 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 and transgenic plants able to synthesise 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 that contain one or more genes which 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 and their seed material can be resistant to herbicides and at the same time also to insect feeding ("stacked" transgenic events). Seed can, for example, have the ability to express an insecticidally active Cry3 protein and at the same time be glyphosate-tolerant. The term "crops" is to be understood as also including crops obtained as a result of conventional methods of breeding or genetic engineering which contain so-called output traits (e.g. improved flavour, storage stability, nutritional content).

In all aspects of the invention, the weeds, e.g. to be controlled and/or growth-inhibited, may be either monocotyledonous (e.g. grassy) and/or dicotyledonous weeds. Preferably the weeds, e.g. to be controlled and/or growth-inhibited, comprise or are

monocotyledonous weeds, more preferably grassy monocotyledonous weeds. In all aspects of the invention, typically, the monocotyledonous (preferably grassy) weeds, e.g. to be controlled and/or growth-inhibited, comprise (e.g. are) weeds from the genus Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cyperus (a genus of sedges), Digitaria, Echinochloa, Eriochloa, Fimbristylis (a genus of sedges), Juncus (a genus of rushes), Leptochloa, Lolium, Monochoria, Panicum, Phalaris, Poa, Rottboellia, Sagittaria, Scirpus (a genus of sedges), Setaria and/or Sorghum; in particular: Alopecurus

myosuroides (ALOMY, English name "blackgrass"), Apera spica-venti, Avena fatua

(AVEFA, English name "wild oats"), Avena ludoviciana, Avena sterilis, Avena sativa (English name "oats" (volunteer)), Brachiaria plantaginia, Bromus tectorum, Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (English name "common barnyard grass", ECHCG), Echinochloa oryzoides, Echinochloa colona or colonum, Eriochloa villosa

(English name "wolly cupgrass"), Leptochloa chinensis, Leptochloa panicoides, Lolium perenne (LOLPE, English name "perennial ryegrass"), Lolium multiflorum (LOLMU, English name "Italian ryegrass"), Lolium persicum (English name "Persian darnel"), Lolium rigidum, Panicum miliaceum (English name "wild proso millet"), Phalaris minor, Phalaris paradoxa, Poa annua, Scirpus maritimus, Scirpus juncoides, Setaria viridis (SETVI, English name "green foxtail"), Setaria faberi (SETFA, English name "giant foxtail"), Setaria lutescens (English name "yellow foxtail") and/or Sorghum halapense (English name "Johnson grass"). In one preferred embodiment of all aspects of the invention, the monocotyledonous weeds, e.g. to be controlled and/or growth-inhibited, are grassy weeds; in which case they typically comprise (e.g. are) weeds from the genus Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Digitaria, Echinochloa, Eriochloa, Leptochloa, Lolium, Monochoria, Panicum, Phalaris, Poa, Rottboellia, Sagittaria, Setaria and/or Sorghum. In one particular embodiment of all aspects of the invention, the grassy monocotyledonous weeds, e.g. to be controlled and/or growth-inhibited, are "warm-season" grassy weeds; in which case they typically comprise (e.g. are) weeds from the genus Brachiaria, Digitaria, Echinochloa, Eriochloa, Leptochloa, Monochoria, Panicum, Setaria and/or Sorghum.

In another particular embodiment of all aspects of the invention, the grassy

monocotyledonous weeds, e.g. to be controlled and/or growth-inhibited, are "cool-season" grassy weeds; in which case they typically comprise (e.g. are) weeds from the genus Agrostis, Alopecurus, Apera, Avena, Bromus, Lolium and/or Poa.

In non-oat cereal crops such as wheat and/or barley, control and/or growth inhibition of weeds from the genus Alopecurus, Apera, Avena, especially Avena fatua, Bromus, Lolium, Phalaris, and/or Setaria is preferred; in particular Alopecurus, Avena (especially Avena fatua), Lolium and/or Setaria (especially Setaria viridis, Setaria lutescens and/or Setaria faberi).

In all aspects of the invention, the weeds, e.g. to be controlled and/or growth-inhibited e.g. by applying a compound of formula (I) or an agrochemically acceptable salt thereof, may in particular be grassy monocotyledonous weeds (e.g. Lolium, Avena, Alopecurus, Phalaris, Apera, Poa, Bromus, Setaria, Sorghum, Echinochloa, Digitaria, Brachiaria, Eriochloa and/or Panicum weeds), which are resistant to one or more ACCase inhibitor herbicides (ACCase = Acetyl-coenzyme A carboxylase) selected from the group consisting of pinoxaden, clodinafop-propargyl, fenoxaprop-P-ethyl, diclofop-methyl, fluazifop-P-butyl, haloxyfop-P-methyl, quizalofop-P-ethyl, propaquizafop, cyhalofop-butyl, clethodim, sethoxydim, cycloxydim, tralkoxydim and butroxydim; and/or which are resistant to glyphosate; and/or which are resistant to one or more ALS inhibitor herbicides (ALS = acetolactate synthase), such as one or more sulfonyl urea herbicides (e.g. iodosulfuron- methyl, mesosulfuron-methyl, tribenuron-methyl, triasulfuron, pyrazosulfuron-ethyl, bensulfuron-methyl, nicosulfuron, or any other sulfonyl urea herbicide disclosed in the Pesticide Manual 2009 edition, British Crop Protection Council) and/or one or more triazolopyrimidine herbicides (e.g. florasulam, pyroxsulam or penoxsulam) and/or one or more pyrimidinyl-thiobenzoate herbicides. Such resistant (in particular ACCase-inhibitor- resistant, glyphosate-resistant, and/or ALS-inhibitor-resistant) grassy weeds can more particularly comprise Lolium multiflorum, Lolium rigidum, Lolium perenne, Avena fatua, Avena sterilis, Alopecurus myosuroides, Phalaris minor, Phalaris paradoxa, Apera spica- venti, Setaria viridis, Setaria faberi, Sorghum halapense, Echinochloa colona, Echinochloa crus-galli and/or Digitaria sanguinalis. In an even more particular embodiment of the invention, the compound of formula (I) or the agrochemicaly acceptable salt thereof can be applied to grassy monocotyledonous weeds (e.g. selected from one of the above- mentioned list(s)):

(a1 ) which are resistant to one or more ACCase inhibitor herbicides (e.g. selected from the above-mentioned list) at least partly by means of mutation (e.g. substitution) of one or more amino acids on the ACCase target site in the weed (e.g. see S.B. Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu. Rev. Plant Biol., 2010, 61 , pp. 317-347, e.g. see pages 325-327 therein in particular Table 3, incorporated herein by reference, for examples of such resistant weeds and/or amino acid substitutions); and/or (a2) which are resistant to glyphosate at least partly by means of mutation (e.g.

substitution) of one or more amino acids on the EPSPS target site in the weed targeted by glyphosate (e.g. see above-mentioned S.B. Powles and Qin Yu article, pp. 327-329); and/or

(a3) which are resistant to one or more ALS inhibitor herbicides (e.g. selected from the above-mentioned list) at least partly by mutation (e.g. substitution) of one or more amino acids on the ALS target site in the weed (e.g. see S.B. Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu. Rev. Plant Biol., 2010, 61 , pp. 317-347, e.g. see pages 322-324 therein in particular Table 2, incorporated herein by reference, for examples of such resistant weeds and/or amino acid substitutions); and/or

(b) which are resistant to: one or more ACCase inhibitor herbicides (e.g. selected from the above-mentioned list), and/or glyphosate or glufosinate, and/or one or more ALS inhibitor herbicides (e.g. selected from the above-mentioned list); at least partly by metabolic-type herbicidal resistance e.g. at least by cytochrome P450-mediated herbicide metabolism (e.g. see S.B. Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu. Rev. Plant Biol., 2010, 61 , pp. 317-347, e.g. see Table 4 on page 328 therein, incorporated herein by reference, for examples of such resistant weeds). Typically, dicotyledonous weeds, e.g. to be controlled, comprise (e.g. are) Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Galium, Ipomoea, Kochia, Nasturtium, Polygonum, Sida, Sinapsis, Solanum, Stellaria, Viola, Veronica and/or Xanthium. Areas under cultivation, and/or the locus (e.g. of weeds and/or of crops of useful plants), are to be understood as including land where the crop plants are already growing as well as land intended for the cultivation of those crop plants. In all aspects of the invention, the rate of application of the compound of formula (I) or the agrochemically acceptable salt thereof is generally from 10 to 10000 g of the compound of formula (I) or the salt thereof per hectare (ha) (measured as the salt-free compound), in particular from 30 to 5000 or from 50 to 3000 g/ha, preferably from 100 to 1500 g/ha, of the compound of formula (I) or the salt thereof (measured as the salt-free compound).

In all aspects of the invention, the compound of formula (I) or salt thereof can be applied pre- and/or post-emergence, but preferably is applied post-emergence.

Compositions, especially herbicidal compositions

In another aspect, the present invention also provides a herbicidal composition, in particular for use in a method of controlling weeds (e.g. monocotyledonous such as grassy weeds) in crops of useful plants, which composition comprises a compound of formula (I) as defined herein or an agrochemically acceptable salt thereof (e.g. a herbicidally effective amount thereof), and a substantially-inert agrochemically acceptable substance (e.g. an agrochemically acceptable carrier or diluent, an agrochemically acceptable solvent, an agrochemically acceptable adjuvant, an an agrochemically acceptable emulsifier / surfactant / surface-active substance, and/or another agrochemically acceptable additive).

In a similar aspect, the present invention provides a herbicidal composition, in particular for use in a method of controlling weeds (e.g. monocotyledonous such as grassy weeds) in crops of useful plants, comprising a compound of formula (I) as defined herein or an agrochemically acceptable salt thereof (e.g. a herbicidally effective amount thereof), and an agrochemically acceptable carrier, diluent and/or solvent therefor.

In one embodiment, the herbicidal composition also comprises one or more further herbicides, as mixture partner(s) for the compound of formula I, and/or a safener. See the combinations and mixtures section herein for more details of examples of these. The invention therefore also relates to a herbicidal composition, such as emulsifiable concentrates, suspension concentrates, oil dispersions, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise a compound of formula I according to the invention, and e.g. which are generally to be selected to suit the intended aims and the prevailing circumstances.

In these compositions, the active ingredient is usually employed in substantially pure form, a solid active ingredient for example in a specific particle size, or, preferably, together with - at least - one of the auxiliaries conventionally used in the art of formulation, such as extenders, for example solvents or solid carriers, or such as surface-active compounds (surfactants). Examples of suitable solvents are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C8 to C12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unexpodized or epoxidized rapeseed, castor, coconut or soya oil, and silicone oils.

Solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly disperse silicas or highly disperse absorbtive polymers. Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are calcite or sand. In addition, a large number of granulated materials of inorganic or organic nature can be used, in particular dolomite or comminuted plant residues. Suitable surface-active compounds are, depending on the type of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties. The surfactants mentioned below are only to be considered as examples; a large number of further surfactants which are conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.

Suitable non-ionic surfactants are, especially, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, of saturated or unsaturated fatty acids or of alkyl phenols which may contain approximately 3 to approximately 30 glycol ether groups and approximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical or

approximately 6 to approximately 18 carbon atoms in the alkyl moiety of the alkyl phenols. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopo-'lypropylene glycol or alkyl polypropylene glycol having 1 to

approximately 10 carbon atoms in the alkyl chain and approximately 20 to approximately 250 ethylene glycol ether groups and approximately 10 to approximately 100 propylene glycol ether groups. Normally, the abovementioned compounds contain 1 to approximately 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene

glycol/polyethylene oxide adducts, tributylpheno-'xypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are, especially, quarternary ammonium salts which generally have at least one alkyl radical of approximately 8 to approximately 22 C atoms as substituents and as further substituents (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2- chloroethyl)ethyhammonium bromide.

Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds. Examples of suitable soaps are the alkali, alkaline earth or (unsubstituted or substituted) ammonium salts of fatty acids having approximately 10 to approximately 22 C atoms, such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which are obtainable for example from coconut or tall oil; mention must also be made of the fatty acid methyl taurates. However, synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates. As a rule, the fatty sulfonates and fatty sulfates are present as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts and they generally have an alkyl radical of approximately 8 to

approximately 22 C atoms, alkyl also to be understood as including the alkyl moiety of acyl radicals; examples which may be mentioned are the sodium or calcium salts of

lignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and a fatty acid radical of approximately 8 to approximately 22 C atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, of dibutyhnaphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate. Also possible are, furthermore, suitable phosphates, such as salts of the phosphoric ester of a p- nonylphenol/(4-14)ethylene oxide adduct, or phospholipids. Further suitable phosphates are tris-esters of phosphoric acid with aliphatic or aromatic alcohols and/or bis-esters of alkyl phosphonic acids with aliphatic or aromatic alcohols, which are a high performance oil-type adjuvant. These tris-esters have been described, for example, in WO0147356, WO0056146, EP-A-0579052 or EP-A-1018299 or are commercially available under their chemical name. Preferred tris-esters of phosphoric acid for use in the new compositions are tris-(2-ethylhexyl) phosphate, tris-n-octyl phosphate and tris-butoxyethyl phosphate, where tris-(2-ethylhexyl) phosphate is most preferred. Suitable bis-ester of alkyl phosphonic acids are bis-(2-ethylhexyl)-(2-ethylhexyl)-phosphonate, bis-(2-ethylhexyl)-(n- octyl)-phosphonate, dibutyl-butyl phosphonate and bis(2-ethylhexyl)-tripropylene- phosphonate, where bis-(2-ethylhexyl)-(n-octyl)-phosphonate is particularly preferred.

The compositions according to the invention can preferably 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 used 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 such as ADIGOR® and MERO®, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® (Rhone-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 C₈-C₂2 fatty acids, especially the methyl derivatives of Ci₂-Ci₈ fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid, being important. Those esters are known as methyl laurate (CAS-1 1 1 -82-0), methyl palmitate (CAS-1 12-39-0) and methyl oleate (CAS-1 12-62- 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. Also, alkoxylated fatty acids can be used as additives in the inventive compositions as well as polymethylsiloxane based additives, which have been described in WO08/037373. The application and action of the oil additives can be further improved by combining them 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 surfactants 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 (Clariant AG). Also preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltrisiloxanes, which are commercially available e.g. as Silwet L-77®, and also perfluorinated surfactants. The concentration of surface-active substances in relation to the total additive is generally from 1 to 30 % by weight. Examples of oil additives that consist of mixtures of oils or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (Syngenta AG, CH) and Actipron® (BP Oil UK Limited, GB). The said surface-active substances may also be used in the formulations alone, that is to say without oil additives.

Furthermore, the addition of an organic solvent to the oil additive/surfactant mixture can contribute to a further enhancement of action. Suitable solvents are, for example,

Solvesso® (ESSO) and Aromatic Solvent® (Exxon Corporation). The concentration of such solvents can be from 10 to 80 % by weight of the total weight. Such oil additives, which may be 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, in order to enhance the activity 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 latices, such as, for example, polyacrylamide, polyvinyl compounds or poly-1 -p-menthene (e.g. Bond®, Courier® or Emerald®) can also be used. Solutions that contain propionic acid, for example Eurogkem Pen-e-trate®, can also be mixed into the spray mixture as activity- enhancing agents. As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of active ingredient of thre formula land 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid adjuvant, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants(% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient. Preferred compositions are composed in particular as follows (% = percent by weight):

Emulsifiable concentrates:

active ingredient: 1 to 95%, preferably 5 to 50%, more preferably 5 to 20% surfactant: 1 to 30%, preferably 10 to 20 %

solvent: 5 to 98%, preferably 70 to 85%

Dusts:

active ingredient: 0.1 to 10%, preferably 2 to 5%,

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates:

active ingredient: 5 to 75%, preferably 10 to 50%, more preferably 10 to

40%

water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to 30%

Oil-based suspension concentrates:

active ingredient: 2 to 75%, preferably 5 to 50%, more preferably 10 to

25%

oil: 94 to 24%, preferably 88 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable powders:

active ingredient: 0.5 to 90%, preferably 1 to 80%, more preferably 25 to

75%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 99%, preferably 15 to 98% Granulates:

active ingredient: 0.5 to 30%, preferably 3 to 25%, more preferably 3 to

15%

solid carrier: 99.5 to 70%, preferably 97 to 85% Preferably, the term "active ingredient" refers to one of the compounds selected from

Tables 1 to 333 shown above (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14). It also refers to mixtures of the compound of formula I, in particular a compound selected from said Tables 1 to 333 (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14), with one or more other herbicides, and/or safeners, which mixtures are specifically disclosed herein e.g. hereinbelow.

The compositions can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers; fertilizers, in particular nitrogen containing fertilizers such as ammonium nitrates and urea as described in WO08/017388, which can enhance the efficacy of the inventive compounds; or other active ingredients for achieving specific effects, for example ammonium or phosphonium salts, in particular halides,

(hydrogen)sulphates, nitrates, (hydrogen)carbonates, citrates, tartrates, formiates and acetates, as described in WO07/068427 and WO07/068428, which also can enhance the efficacy of the inventive compounds and which can be used in combination with penetration enhancers such as alkoxalated fatty acids; bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides. The herbicidal compositions according to the invention are generally prepared, e.g. in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds I for the preparation of these compositions are also a subject of the invention.

The application methods for the herbicidal compositions, and for the methods of controlling weeds as described herein, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring (especially spraying) - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the herbicidal compositions for controlling weeds of the abovementioned type, are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient in the herbicidal composition. In all aspects of the invention, the rate of application of the compound of formula (I) or the agrochemically acceptable salt thereof is generally from 10 to 10000 g of the compound of formula (I) or the salt thereof per hectare (ha) (measured as the salt-free compound), in particular from 30 to 5000 or from 50 to 3000 g/ha, preferably from 100 to 1500 g/ha, of the compound of formula (I) or the salt thereof (measured as the salt-free compound).

A preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field. The herbicidal compositions according to the invention are also suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type. The propagation material can be treated with the compositions prior to planting, for example seed can be treated prior to sowing. Alternatively, the compositions can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention.

Further methods of application of the compositions according to the invention comprise drip application onto the soil, dipping of parts of plants such as roots bulbs or tubers, drenching the soil, as well as soil injection. These methods are known in the art.

In order to apply a compound of formula I as a herbicide to a weed, or to a locus of weed, a compound of formula I is usually formulated into a herbicidal composition which includes, in addition to the compound of formula I, a suitable inert diluent or carrier and, optionally, a formulation adjuvant in form of a surface active agent (SFA) as described herein or, for example, in EP-B-1062217. SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula I. The composition is generally used for the control of pests such that a compound of formula I is applied at a rate of from 0.1 g to10kg per hectare, preferably from 1 g to 6kg per hectare, more preferably from 1 g to 1 kg per hectare. When used in a seed dressing, a compound of formula I is used at a rate of 0.0001 g to

10g (for example 0.001 g or 0.05g), preferably 0.005g to 10g, more preferably 0.005g to 4g, per kilogram of seed.

In one aspect of the invention, the present invention provides a herbicidal composition, in particular for use in a method of controlling weeds (e.g. monocotyledonous such as grassy weeds) in crops of useful plants, comprising a compound of formula (I) as defined herein or an agrochemically acceptable salt thereof (e.g. a herbicidally effective amount thereof), and an agrochemically acceptable carrier, diluent and/or solvent therefor. The compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), oil-based suspension concentrate (OD), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose en-visaged and the physical, chemical and biological properties of the compound of formula I.

Dustable powders (DP) may be prepared by mixing a compound of formula I with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula I with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a

polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG). Wettable powders (WP) may be prepared by mixing a compound of formula I with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG). Granules (GR) may be formed either by granulating a mixture of a compound of formula I and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula I (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr,

diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula I (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compound of formula I in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula I in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as C₈-Ci₀ fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of formula I either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated

hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of formula I is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a water-in- oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble herbicides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula I. SCs may be prepared by ball or bead milling the solid compound of formula I in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula I may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.

Oil-based suspension concentrate (OD) may be prepared similarly by suspending finely divided insoluble solid particles of a compound of formula I in an organic fluid (for example at least one mineral oil or vegetable oil). ODs may further comprise at least one

penetration promoter (for example an alcohol ethoxylate or a related compound), at least one non-ionic surfactants and/or at least one anionic surfactant, and optionally at least one additive from the group of emulsifiers, foam-inhibiting agents, preservatives, anti-oxidants, dyestuffs, and/or inert filler materials. An OD is intended and suitable for dilution with water before use to produce a spray solution with sufficient stability to allow spray application through appropriate equipment.

Aerosol formulations comprise a compound of formula I and a suitable propellant (for example n-butane). A compound of formula I may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.

Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula I and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of formula I and they may be used for seed treatment. A compound of formula I may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

A compound of formula I may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule

suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC, OD and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).

A composition of the present invention may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula I). Such additives include surface active agents (SFAs), spray additives based on oils, for example certain mineral oils, vegetable oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula I). Increasing the effect of a compound of formula I may for example be achieved by adding ammonium and/or phosphonium salts, and/or optionally at least one penetration promotor such as fatty alcohol alkoxylates (for example rape oil methyl ester) or vegetable oil esters.

Wetting agents, dispersing agents and emulsifying agents may be surface active agents (SFAs) of the cationic, anionic, amphoteric or non-ionic type. Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic

monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium

dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di- /^'sopropyl- and tri-/^'sopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated),

sulphosuccinamates, paraffin or define sulphonates, taurates and lignosulphonates.

Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

A compound of formula I may be applied by any of the known means of applying herbicidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.

A compound of formula I may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ODs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of formula I (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.

Combinations and mixtures

The compound of formula (I) or the agrochemically acceptable salt thereof may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as one or more further herbicides, synergist(s), safener(s) and/or plant growth regulator(s) where appropriate, preferably one or more further herbicides and/or a safener.

Therefore, the invention also provides a herbicidal composition, e.g. for use in a method of controlling weeds (e.g. monocotyledonous such as grassy weeds) in crops of useful plants, which comprises a compound of formula (I) as defined herein or an agrochemically acceptable salt thereof (e.g. a herbicidally effective amount thereof), and: (i) one or more further herbicide(s) as mixture partner(s) for the compound of formula (I); and/or

(ii) a safener. The compounds of formula (I) or the salt thereof according to, or as used in, the invention can also be used in combination with one or more further herbicides. Preferably, in these mixtures, the compound of the formula I is one of those compounds listed in Tables 1 to 333 herein, and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14 as disclosed or illustrated herein. The following mixtures of the compound of formula I are particularly noteworthy:

compound of formula I + acetochlor, compound of formula I + acifluorfen, compound of formula I + acifluorfen-sodium, compound of formula I + aclonifen, compound of formula I + acrolein, compound of formula I + alachlor, compound of formula I + alloxydim, compound of formula I + allyl alcohol, compound of formula I + ametryn, compound of formula I + amicarbazone, compound of formula I + amidosulfuron, compound of formula I + aminopyralid, compound of formula I + amitrole, compound of formula I + ammonium sulfamate, compound of formula I + anilofos, compound of formula I + asulam, compound of formula I + atraton, compound of formula I + atrazine, compound of formula I + azimsulfuron, compound of formula I + BCPC, compound of formula I + beflubutamid, compound of formula I + benazolin, compound of formula I + benfluralin, compound of formula I + benfuresate, compound of formula I + bensulfuron, compound of formula I + bensulfuron-methyl, compound of formula I + bensulide, compound of formula I + bentazone, compound of formula I + benzfendizone, compound of formula I +

benzobicyclon, compound of formula I + benzofenap, compound of formula I + bifenox, compound of formula I + bilanafos, compound of formula I + bispyribac, compound of formula I + bispyribac-sodium, compound of formula I + borax, compound of formula I + bromacil, compound of formula I + bromobutide, compound of formula I + bromoxynil, compound of formula I + butachlor, compound of formula I + butafenacil, compound of formula I + butamifos, compound of formula I + butralin, compound of formula I + butroxydim, compound of formula I + butylate, compound of formula I + cacodylic acid, compound of formula I + calcium chlorate, compound of formula I + cafenstrole, compound of formula I + carbetamide, compound of formula I + carfentrazone, compound of formula I + carfentrazone-ethyl, compound of formula I + CDEA, compound of formula I + CEPC, compound of formula I + chlorflurenol, compound of formula I + chlorflurenol-methyl, compound of formula I + chloridazon, compound of formula I + chlorimuron, compound of formula I + chlorimuron-ethyl, compound of formula I + chloroacetic acid, compound of formula I + chlorotoluron, compound of formula I + chlorpropham, compound of formula I + chlorsulfuron, compound of formula I + chlorthal, compound of formula I + chlorthal- dimethyl, compound of formula I + cinidon-ethyl, compound of formula I + cinmethylin, compound of formula I + cinosulfuron, compound of formula I + cisanilide, compound of formula I + clethodim, compound of formula I + clodinafop, compound of formula I + clodinafop-propargyl, compound of formula I + clomazone, compound of formula I + clomeprop, compound of formula I + clopyralid, compound of formula I + cloransulam, compound of formula I + cloransulam-methyl, compound of formula I + CMA, compound of formula I + 4-CPB, compound of formula I + CPMF, compound of formula I + 4-CPP, compound of formula I + CPPC, compound of formula I + cresol, compound of formula I + cumyluron, compound of formula I + cyanamide, compound of formula I + cyanazine, compound of formula I + cycloate, compound of formula I + cyclosulfamuron, compound of formula I + cycloxydim, compound of formula I + cyhalofop, compound of formula I + cyhalofop-butyl, compound of formula I + 2,4-D, compound of formula I + 3,4-DA, compound of formula I + daimuron, compound of formula I + dalapon, compound of formula I + dazomet, compound of formula I + 2,4-DB, compound of formula I + 3,4-DB, compound of formula I + 2,4-DEB, compound of formula I + desmedipham, compound of formula I + dicamba, compound of formula I + dichlobenil, compound of formula I + ortho- dichlorobenzene, compound of formula I + para-dichlorobenzene, compound of formula I + dichlorprop, compound of formula I + dichlorprop-P, compound of formula I + diclofop, compound of formula I + diclofop-methyl, compound of formula I + diclosulam, compound of formula I + difenzoquat, compound of formula I + difenzoquat metilsulfate, compound of formula I + diflufenican, compound of formula I + diflufenzopyr, compound of formula I + dimefuron, compound of formula I + dimepiperate, compound of formula I + dimethachlor, compound of formula I + dimethametryn, compound of formula I + dimethenamid, compound of formula I + dimethenamid-P, compound of formula I + dimethipin, compound of formula I + dimethylarsinic acid, compound of formula I + dinitramine, compound of formula I + dinoterb, compound of formula I + diphenamid, compound of formula I + diquat, compound of formula I + diquat dibromide, compound of formula I + dithiopyr, compound of formula I + diuron, compound of formula I + DNOC, compound of formula I + 3,4-DP, compound of formula I + DSMA, compound of formula I + EBEP, compound of formula I + endothal, compound of formula I + EPTC, compound of formula I + esprocarb, compound of formula I + ethalfluralin, compound of formula I + ethametsulfuron, compound of formula I + ethametsulfuron-methyl, compound of formula I + ethofumesate, compound of formula I + ethoxyfen, compound of formula I + ethoxysulfuron, compound of formula I +

etobenzanid, compound of formula I + fenoxaprop-P, compound of formula I + fenoxaprop- P-ethyl, compound of formula I + fenoxasulfone (CAS Reg. No. 639826-16-7), compound of formula I + fentrazamide, compound of formula I + ferrous sulfate, compound of formula I + flamprop-M, compound of formula I + flazasulfuron, compound of formula I +

florasulam, compound of formula I + fluazifop, compound of formula I + fluazifop-butyl, compound of formula I + fluazifop-P, compound of formula I + fluazifop-P-butyl, compound of formula I + flucarbazone, compound of formula I + flucarbazone-sodium, compound of formula I + flucetosulfuron, compound of formula I + fluchloralin, compound of formula I + flufenacet, compound of formula I + flufenpyr, compound of formula I + flufenpyr-ethyl, compound of formula I + flumetsulam, compound of formula I + flumiclorac, compound of formula I + flumiclorac-pentyl, compound of formula I + flumioxazin, compound of formula I + fluometuron, compound of formula I + fluoroglycofen, compound of formula I + fluoroglycofen-ethyl, compound of formula I + flupropanate, compound of formula I + flupyrsulfuron, compound of formula I + flupyrsulfuron-methyl-sodium, compound of formula I + flurenol, compound of formula I + fluridone, compound of formula I +

flurochloridone, compound of formula I + fluroxypyr, compound of formula I + fluroxypyr- meptyl, compound of formula I + fluroxypyr-butometyl, compound of formula I + flurtamone, compound of formula I + fluthiacet, compound of formula I + fluthiacet-methyl, compound of formula I + fomesafen, compound of formula I + foramsulfuron, compound of formula I + fosamine, compound of formula I + glufosinate, compound of formula I + glufosinate- ammonium, compound of formula I + glufosinate-P, compound of formula I + glyphosate, compound of formula I + halosulfuron, compound of formula I + halosulfuron-methyl, compound of formula I + haloxyfop, compound of formula I + haloxyfop-P, compound of formula I + HC-252, compound of formula I + hexazinone, compound of formula I + imazamethabenz, compound of formula I + imazamethabenz-methyl, compound of formula I + imazamox, compound of formula I + imazapic, compound of formula I + imazapyr, compound of formula I + imazaquin, compound of formula I + imazethapyr, compound of formula I + imazosulfuron, compound of formula I + indanofan, compound of formula I + iodomethane, compound of formula I + iodosulfuron, compound of formula I +

iodosulfuron-methyl-sodium, compound of formula I + ioxynil, compound of formula I + ipfencarbazone (CAS Reg. No. 212201 -70-2), compound of formula I + isoproturon, compound of formula I + isouron, compound of formula I + isoxaben, compound of formula I + isoxachlortole, compound of formula I + isoxaflutole, compound of formula I + karbutilate, compound of formula I + lactofen, compound of formula I + lenacil, compound of formula I + linuron, compound of formula I + MAA, compound of formula I + MAMA, compound of formula I + MCPA, compound of formula I + MCPA-thioethyl, compound of formula I + MCPB, compound of formula I + mecoprop, compound of formula I + mecoprop-P, compound of formula I + mefenacet, compound of formula I + mefluidide, compound of formula I + mesosulfuron, compound of formula I + mesosulfuron-methyl, compound of formula I + mesotrione, compound of formula I + metam, compound of formula I + metamifop, compound of formula I + metamitron, compound of formula I + metazachlor, compound of formula I + metazosulfuron (NC-620, CAS Reg. No. 868680-84- 6), compound of formula I + methabenzthiazuron, compound of formula I + methylarsonic acid, compound of formula I + methyldymron, compound of formula I + methyl

isothiocyanate, compound of formula I + metobenzuron, compound of formula I + metolachlor, compound of formula I + S-metolachlor, compound of formula I + metosulam, compound of formula I + metoxuron, compound of formula I + metribuzin, compound of formula I + metsulfuron, compound of formula I + metsulfuron-methyl, compound of formula I + MK-616, compound of formula I + molinate, compound of formula I + monolinuron, compound of formula I + MSMA, compound of formula I + naproanilide, compound of formula I + napropamide, compound of formula I + naptalam, compound of formula I + neburon, compound of formula I + nicosulfuron, compound of formula I + nonanoic acid, compound of formula I + norflurazon, compound of formula I + oleic acid (fatty acids), compound of formula I + orbencarb, compound of formula I +

orthosulfamuron, compound of formula I + oryzalin, compound of formula I + oxadiargyl, compound of formula I + oxadiazon, compound of formula I + oxasulfuron, compound of formula I + oxaziclomefone, compound of formula I + oxyfluorfen, compound of formula I + paraquat, compound of formula I + paraquat dichloride, compound of formula I + pebulate, compound of formula I + pendimethalin, compound of formula I + penoxsulam, compound of formula I + pentachlorophenol, compound of formula I + pentanochlor, compound of formula I + pentoxazone, compound of formula I + pethoxamid, compound of formula I + petrolium oils, compound of formula I + phenmedipham, compound of formula I + phenmedipham-ethyl, compound of formula I + picloram, compound of formula I + picolinafen, compound of formula I + pinoxaden, compound of formula I + piperophos, compound of formula I + potassium arsenite, compound of formula I + potassium azide, compound of formula I + pretilachlor, compound of formula I + primisulfuron, compound of formula I + primisulfuron-methyl, compound of formula I + prodiamine, compound of formula I + profluazol, compound of formula I + profoxydim, compound of formula I + prometon, compound of formula I + prometryn, compound of formula I + propachlor, compound of formula I + propanil, compound of formula I + propaquizafop, compound of formula I + propazine, compound of formula I + propham, compound of formula I + propisochlor, compound of formula I + propoxycarbazone, compound of formula I + propoxycarbazone-sodium, compound of formula I + propyrisulfuron (TH-547, CAS Reg. No. 570415-88-2), compound of formula I + propyzamide, compound of formula I + prosulfocarb, compound of formula I + prosulfuron, compound of formula I + pyraclonil, compound of formula I + pyraflufen, compound of formula I + pyraflufen-ethyl, compound of formula I + pyrazolynate, compound of formula I + pyrazosulfuron, compound of formula I + pyrazosulfuron-ethyl, compound of formula I + pyrazoxyfen, compound of formula I + pyribenzoxim, compound of formula I + pyributicarb, compound of formula I + pyridafol, compound of formula I + pyridate, compound of formula I + pyriftalid, compound of formula I + pyriminobac, compound of formula I + pyriminobac-methyl, compound of formula I + pyrimisulfan, compound of formula I + pyrithiobac, compound of formula I + pyrithiobac- sodium, compound of formula I + quinclorac, compound of formula I + quinmerac, compound of formula I + quinoclamine, compound of formula I + quizalofop, compound of formula I + quizalofop-P, compound of formula I + rimsulfuron, compound of formula I + sethoxydim, compound of formula I + siduron, compound of formula I + simazine, compound of formula I + simetryn, compound of formula I + SMA, compound of formula I + sodium arsenite, compound of formula I + sodium azide, compound of formula I + sodium chlorate, compound of formula I + sulcotrione, compound of formula I + sulfentrazone, compound of formula I + sulfometuron, compound of formula I + sulfometuron-methyl, compound of formula I + sulfosate, compound of formula I + sulfosulfuron, compound of formula I + sulfuric acid, compound of formula I + tar oils, compound of formula I + 2,3,6- TBA, compound of formula I + TCA, compound of formula I + TCA-sodium, compound of formula I + tebuthiuron, compound of formula I + tepraloxydim, compound of formula I + terbacil, compound of formula I + terbumeton, compound of formula I + terbuthylazine, compound of formula I + terbutryn, compound of formula I + thenylchlor, compound of formula I + thiazopyr, compound of formula I + thifensulfuron, compound of formula I + thifensulfuron-methyl, compound of formula I + thiobencarb, compound of formula I + tiocarbazil, compound of formula I + topramezone, compound of formula I + tralkoxydim, compound of formula I + tri-allate, compound of formula I + triasulfuron, compound of formula I + triaziflam, compound of formula I + tribenuron, compound of formula I + tribenuron-methyl, compound of formula I + tricamba, compound of formula I + triclopyr, compound of formula I + trietazine, compound of formula I + trifloxysulfuron, compound of formula I + trifloxysulfuron-sodium, compound of formula I + trifluralin, compound of formula I + triflusulfuron, compound of formula I + triflusulfuron-methyl, compound of formula I + trihydroxytriazine, compound of formula I + tritosulfuron, compound of formula I + [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester (CAS Reg. No. 353292-31 -6), compound of formula I + 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo)-1 H-1 ,2,4-triazol-1 - ylcarbonylsulfamoyl]-5-methylthiophene-3-carboxylic acid (BAY636), compound of formula I + BAY747 (CAS Reg. No. 335104-84-2), compound of formula I + topramezone (CAS Reg. No. 210631 -68-8), compound of formula I + 4-hydroxy-3-[[2-[(2-methoxyethoxy)- methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]-bicyclo[3.2.1 ]oct-3-en-2-one (which is bicyclopyrone, CAS Reg. No. 352010-68-5), compound of formula I + 4-hydroxy-3-[[2-(3- methoxypropyl)-6-(difluoromethyl)-3-pyridinyl]carbonyl]-bicyclo[3.2.1 ]oct-3-en-2-one, compound of formula I + saflufenacil (which is /V'-{2-chloro-4-fluoro-5-[1 ,2,3,6-tetrahydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1 -yl]benzoyl}-/V-isopropyl-/V-methylsulfamide, CAS Reg. No. 372137-35-4), compound of formula I + iofensulfuron (which is 1 -(2- iodophenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)urea, CAS Reg. No. 1 144097- 22-2), compound of formula I + iofensulfuron-sodium (which is sodium N-(2- iodophenylsulfonyl)-/V'-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)carbamimidate, CAS Reg. No. 1 144097-30-2), compound of formula I + clacyfos (which is dimethyl [(1 f?S)-1 -(2,4- dichlorophenoxyacetoxy)ethyl]phosphonate, also named Ivxiancaolin or IGxiancaolin, CAS Reg. No. 215655-76-8), compound of formula I + cyclopyrimorate (which is 6-chloro-3-(2- cyclopropyl-6-methylphenoxy)pyridazin-4-yl morpholine-4-carboxylate, CAS Reg. No.

499231 -24-2), compound of formula I + aminocyclopyrachlor (which is 6-amino-5-chloro-2- cyclopropylpyrimidine-4-carboxylic acid, CAS Reg. No. 858956-08-8), compound of formula I + aminocyclopyrachlor-methyl (which is methyl 6-amino-5-chloro-2- cyclopropylpyrimidine-4-carboxylate, CAS Reg. No. 858954-83-3), compound of formula I + aminocyclopyrachlor-potassium (which is potassium 6-amino-5-chloro-2- cyclopropylpyrimidine-4-carboxylate, CAS Reg. No. 858956-35-1 ), compound of formula I + halauxifen (which is 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylic acid, CAS Reg. No. 943832-60-8), compound of formula I + halauxifen-methyl (which is methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylate, CAS Reg. No. 943831 -98-9), or compound of formula I + triafamone (which is /V-[2-[(4,6-dimethoxy-1 ,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-/V-methyl-1 , 1 - difluoromethanesulfonamide, CAS Reg. No. 874195-61 -6). The mixing partners for the compound of formula I may also be in the form of an ester or an agrochemically acceptable salt thereof, as mentioned e.g. in The Pesticide Manual, 12th Edition (BCPC) 2000, or 15^th edition, 2009, British Crop Production Council. For applications in cereals, the following mixtures are preferred: compound of formula I + aclonifen, compound of formula I + amidosulfuron, compound of formula I + aminopyralid, compound of formula I + beflubutamid, compound of formula I + benfluralin, compound of formula I + bifenox, compound of formula I + bromoxynil, compound of formula I + butafenacil, compound of formula I + carbetamide, compound of formula I + carfentrazone, compound of formula I + carfentrazone-ethyl, compound of formula I + chlorotoluron, compound of formula I + chlorpropham, compound of formula I + chlorsulfuron, compound of formula I + cinidon-ethyl, compound of formula I + clodinafop, compound of formula I + clodinafop-propargyl, compound of formula I + clopyralid, compound of formula I + 2,4-D, compound of formula I + dicamba, compound of formula I + dichlobenil, compound of formula I + dichlorprop, compound of formula I + diclofop, compound of formula I + diclofop-methyl, compound of formula I + difenzoquat, compound of formula I +

difenzoquat metilsulfate, compound of formula I + diflufenican, compound of formula I + diquat, compound of formula I + diquat dibromide, compound of formula I + fenoxaprop-P, compound of formula I + fenoxaprop-P-ethyl, compound of formula I + flamprop-M, compound of formula I + florasulam, compound of formula I + fluazifop-P-butyl, compound of formula I + flucarbazone, compound of formula I + flucarbazone-sodium, compound of formula I + flufenacet, compound of formula I + flupyrsulfuron, compound of formula I + flupyrsulfuron-methyl-sodium, compound of formula I + flurochloridone, compound of formula I + fluroxypyr, compound of formula I + fluroxypyr-meptyl, compound of formula I + fluroxypyr-butometyl, compound of formula I + flurtamone, compound of formula I + imazamethabenz-methyl, compound of formula I + imazamox, compound of formula I + iodosulfuron, compound of formula I + iodosulfuron-methyl-sodium, compound of formula I + ioxynil, compound of formula I + isoproturon, compound of formula I + linuron, compound of formula I + MCPA, compound of formula I + mecoprop, compound of formula I + mecoprop-P, compound of formula I + mesosulfuron, compound of formula I +

mesosulfuron-methyl, compound of formula I + mesotrione, compound of formula I + metribuzin, compound of formula I + metsulfuron, compound of formula I + metsulfuron- methyl, compound of formula I + pendimethalin, compound of formula I + picolinafen, compound of formula I + pinoxaden, compound of formula I + prodiamine, compound of formula I + propanil, compound of formula I + propoxycarbazone, compound of formula I + propoxycarbazone-sodium, compound of formula I + prosulfocarb, compound of formula I + pyrasulfotole, compound of formula I + pyridate, compound of formula I + pyroxasulfone (KI H-485), compound of formula I + pyroxsulam compound of formula I + sulfosulfuron, compound of formula 1 + tembotrione, compound of formula I + terbutryn, compound of formula I + thifensulfuron, compound of formula I + thiencarbazone, compound of formula I + thifensulfuron-methyl, compound of formula I + topramezone, compound of formula I + tralkoxydim, compound of formula I + tri-allate, compound of formula I + triasulfuron, compound of formula I + tribenuron, compound of formula I + tribenuron-methyl, compound of formula I + trifluralin, compound of formula I + trinexapac-ethyl, compound of formula I + tritosulfuron, compound of formula I + 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-

(trifluoromethyl)-3-pyridinyl]carbonyl]-bicyclo[3.2.1 ]oct-3-en-2-one (which is bicyclopyrone, CAS Reg. No. 352010-68-5), compound of formula I + iofensulfuron (which is 1 -(2- iodophenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)urea, CAS Reg. No. 1 144097- 22-2), compound of formula I + iofensulfuron-sodium (which is sodium N-(2- iodophenylsulfonyl)-/V'-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)carbamimidate, CAS Reg. No. 1 144097-30-2), compound of formula I + halauxifen (which is 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, CAS Reg. No. 943832-60-8), or compound of formula I + halauxifen-methyl (which is methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate, CAS Reg. No. 943831 -98-9). For applications in cereals, the following mixtures are particularly preferred: a mixture comprising a compound of formula (I) + amidosulfuron, compound of formula (I) + aminopyralid, compound of formula (I) + beflubutamid, compound of formula (I) + bromoxynil, compound of formula (I) + carfentrazone, compound of formula (I) + carfentrazone-ethyl, compound of formula (I) + chlorotoluron, compound of formula (I) + chlorsulfuron, compound of formula (I) + clodinafop, compound of formula (I) + clodinafop- propargyl, compound of formula (I) + clopyralid, 2,4-D, compound of formula (I) + dicamba, compound of formula (I) + difenzoquat, compound of formula (I) + difenzoquat metilsulfate, compound of formula (I) + diflufenican, compound of formula (I) + fenoxaprop-P, compound of formula (I) + fenoxaprop-P-ethyl, compound of formula (I) + florasulam, compound of formula (I) + flucarbazone, compound of formula (I) + flucarbazone-sodium, compound of formula (I) + flufenacet, compound of formula (I) + flupyrsulfuron, compound of formula (I) + flupyrsulfuron-methyl-sodium, compound of formula (I) + fluroxypyr, compound of formula I + fluroxypyr-meptyl, compound of formula I + fluroxypyr-butometyl, compound of formula (I) + flurtamone, compound of formula (I) + iodosulfuron, compound of formula (I) + iodosulfuron-methyl-sodium, compound of formula (I) + MCPA, compound of formula (I) + mesosulfuron, compound of formula (I) + mesosulfuron-methyl, compound of formula (I) + metsulfuron, compound of formula (I) + metsulfuron-methyl, compound of formula (I) + pendimethalin, compound of formula (I) + picolinafen, compound of formula (I) + pinoxaden, compound of formula (I) + prosulfocarb, compound of formula (I) + pyrasulfotole, compound of formula (I) + pyroxasulfone (KIH-485), compound of formula (I) + pyroxsulam, compound of formula (I) + sulfosulfuron, compound of formula (I) + thifensulfuron, compound of formula (I) + thifensulfuron-methyl, compound of formula (I) + tralkoxydim, compound of formula (I) + triasulfuron, compound of formula (I) + tribenuron, compound of formula (I) + tribenuron-methyl, compound of formula (I) + trifluralin, compound of formula (I) + trinexapac-ethyl, compound of formula (I) + tritosulfuron, compound of formula I + 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3- pyridinyl]carbonyl]-bicyclo[3.2.1 ]oct-3-en-2-one (which is bicyclopyrone, CAS RN 352010- 68-5), compound of formula I + iofensulfuron (which is 1 -(2-iodophenylsulfonyl)-3-(4- methoxy-6-methyl-1 ,3,5-triazin-2-yl)urea, CAS Reg. No. 1 144097-22-2), compound of formula I + iofensulfuron-sodium (which is sodium /V-(2-iodophenylsulfonyl)-/V'-(4-methoxy- 6-methyl-1 ,3,5-triazin-2-yl)carbamimidate, CAS Reg. No. 1 144097-30-2), compound of formula I + halauxifen (which is 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methoxyphenyl)pyridine-2-carboxylic acid, CAS Reg. No. 943832-60-8), or compound of formula I + halauxifen-methyl (which is methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methoxyphenyl)pyridine-2-carboxylate, CAS Reg. No. 943831 -98-9).

For applications in rice, the following mixtures are preferred: compound of formula (I) + azimsulfuron, compound of formula (I) + bensulfuron, compound of formula (I) +

bensulfuron-methyl, compound of formula (I) + benzobicyclon, compound of formula (I) + benzofenap, compound of formula (I) + bispyribac, compound of formula (I) + bispyribac- sodium, compound of formula (I) + butachlor, compound of formula (I) + cafenstrole, compound of formula (I) + cinosulfuron, compound of formula (I) + clomazone, compound of formula (I) + clomeprop, compound of formula (I) + cyclosulfamuron, compound of formula (I) + cyhalofop, compound of formula (I) + cyhalofop-butyl, compound of formula (I) + 2,4-D, compound of formula (I) + daimuron, compound of formula (I) + dicamba, compound of formula (I) + diquat, compound of formula (I) + diquat dibromide, compound of formula (I) + esprocarb, compound of formula (I) + ethoxysulfuron, compound of formula (I) + fenoxaprop-P, compound of formula (I) + fenoxaprop-P-ethyl, compound of formula I + fenoxasulfone (CAS Reg. No. 639826-16-7), compound of formula (I) + fentrazamide, compound of formula (I) + florasulam, compound of formula (I) + glufosinate-ammonium, compound of formula (I) + glyphosate, compound of formula (I) + halosulfuron, compound of formula (I) + halosulfuron-methyl, compound of formula (I) + imazosulfuron, compound of formula I + ipfencarbazone (CAS Reg. No. 212201 -70-2), compound of formula (I) + MCPA, compound of formula (I) + mefenacet, compound of formula (I) + mesotrione, compound of formula (I) + metamifop, compound of formula I + metazosulfuron (NC-620, CAS Reg. No. 868680-84-6), compound of formula (I) + metsulfuron, compound of formula (I) + metsulfuron-methyl, compound of formula (I) + n-methyl glyphosate, compound of formula (I) + orthosulfamuron, compound of formula (I) + oryzalin, compound of formula (I) + oxadiargyl, compound of formula (I) + oxadiazon, compound of formula (I) + paraquat dichloride, compound of formula (I) + pendimethalin, compound of formula (I) +

penoxsulam, compound of formula (I) + pretilachlor, compound of formula (I) + profoxydim, compound of formula (I) + propanil, compound of formula I + propyrisulfuron (TH-547, CAS Reg. No. 570415-88-2), compound of formula (I) + pyrazolynate, compound of formula (I) + pyrazosulfuron, compound of formula (I) + pyrazosulfuron-ethyl, compound of formula (I) + pyrazoxyfen, compound of formula (I) + pyribenzoxim, compound of formula (I) + pyriftalid, compound of formula (I) + pyriminobac, compound of formula (I) + pyriminobac-methyl, compound of formula (I) + pyrimisulfan, compound of formula (I) + quinclorac, compound of formula (I) + tefuryltrione, compound of formula (I) + triasulfuron, compound of formula (I) + trinexapac-ethyl, compound of formula I + halauxifen (which is 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, CAS Reg. No. 943832-60-8), compound of formula I + halauxifen-methyl (which is methyl 4-amino-3-chloro-6-(4-chloro- 2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate, CAS Reg. No. 943831 -98-9), or compound of formula I + triafamone (which is /V-[2-[(4,6-dimethoxy-1 ,3,5-triazin-2- yl)carbonyl]-6-fluorophenyl]-/V-methyl-1 ,1 -difluoromethanesulfonamide, CAS Reg. No. 874195-61 -6).

For applications in rice, the following mixtures are particularly preferred: a mixture comprising a compound of formula (I) + azimsulfuron, compound of formula (I) + bensulfuron, compound of formula (I) + bensulfuron-methyl, compound of formula (I) + benzobicyclon, compound of formula (I) + benzofenap, compound of formula (I) + bispyribac, compound of formula (I) + bispyribac-sodium, compound of formula (I) + clomazone, compound of formula (I) + clomeprop, compound of formula (I) + cyhalofop, compound of formula (I) + cyhalofop-butyl, compound of formula (I) + 2,4-D, compound of formula (I) + daimuron, compound of formula (I) + dicamba, compound of formula (I) + esprocarb, compound of formula (I) + ethoxysulfuron, compound of formula (I) + fenoxaprop-P, compound of formula (I) + fenoxaprop-P-ethyl, compound of formula I + fenoxasulfone (CAS Reg. No. 639826-16-7), compound of formula (I) + fentrazamide, compound of formula (I) + florasulam, compound of formula (I) + halosulfuron, compound of formula (I) + halosulfuron-methyl, compound of formula (I) + imazosulfuron, compound of formula I + ipfencarbazone (CAS Reg. No. 212201 -70-2), compound of formula (I) + MCPA, compound of formula (I) + mefenacet, compound of formula (I) + mesotrione, compound of formula I + metazosulfuron (NC-620, CAS Reg. No. 868680-84-6), compound of formula (I) + metsulfuron, compound of formula (I) + metsulfuron-methyl, compound of formula (I) + orthosulfamuron, compound of formula (I) + oxadiargyl, compound of formula (I) + oxadiazon, compound of formula (I) + pendimethalin, compound of formula (I) + penoxsulam, compound of formula (I) + pretilachlor, compound of formula I + propyrisulfuron (TH-547, CAS Reg. No. 570415-88-2), compound of formula (I) + pyrazolynate, compound of formula (I) + pyrazosulfuron, compound of formula (I) + pyrazosulfuron-ethyl, compound of formula (I) + pyrazoxyfen, compound of formula (I) + pyribenzoxim, compound of formula (I) + pyriftalid, compound of formula (I) + pyriminobac, compound of formula (I) + pyriminobac-methyl, compound of formula (I) + pyrimisulfan, compound of formula (I) + quinclorac, compound of formula (I) + tefuryltrione, compound of formula (I) + triasulfuron, compound of formula (I) + trinexapac-ethyl, compound of formula I + halauxifen (which is 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylic acid, CAS Reg. No. 943832-60-8), compound of formula I + halauxifen-methyl (which is methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylate, CAS Reg. No. 943831 -98-9), or compound of formula I + triafamone (which is /V-[2-[(4,6-dimethoxy-1 ,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-/V-methyl-1 ,1 - difluoromethanesulfonamide, CAS Reg. No. 874195-61 -6).

In a particularly preferred embodiment, whether or not one or more further herbicides are used, the compounds of formula (I) or the salt thereof according to the invention can be used in combination with a safener. Preferably, in these mixtures, the compound of the formula (I) is one of those compounds listed in Tables 1 to 333 herein, and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14 as disclosed or illustrated herein. The following mixtures with safeners, especially, come into consideration: compound of formula (I) + cloquintocet-mexyl, compound of formula (I) + cloquintocet acid or an agrochemically acceptable salt thereof, compound of formula (I) + cyprosulfamide, compound of formula (I) + fenchlorazole-ethyl, compound of formula (I) + fenchlorazole acid or an agrochemically acceptable salt thereof, compound of formula (I) + mefenpyr- diethyl, compound of formula (I) + mefenpyr diacid, compound of formula (I) + isoxadifen- ethyl, compound of formula (I) + isoxadifen acid, compound of formula (I) + furilazole, compound of formula (I) + furilazole R isomer, compound of formula (I) + benoxacor, compound of formula (I) + dichlormid, compound of formula (I) + AD-67, compound of formula (I) + oxabetrinil, compound of formula (I) + cyometrinil, compound of formula (I) + cyometrinil Z-isomer, compound of formula (I) + fenclorim, compound of formula (I) + naphthalic anhydride, compound of formula (I) + flurazole, compound of formula (I) + N-(2- methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide, compound of formula (I) + CL 304,415, compound of formula (I) + dicyclonon, compound of formula (I) + fluxofenim, compound of formula (I) + DKA-24, compound of formula (I) + R-29148 and compound of formula (I) + PPG-1292.

The mixing partners of the compound of formula I may also be in the form of an ester or an agrochemically acceptable salt, as mentioned e.g. in The Pesticide Manual, 12th Edition (BCPC), 2000, or 15^th edition, 2009, British Crop Production Council.

The above-mentioned safeners and herbicides are described, for example, in the Pesticide Manual, 15^th Edition, British Crop Protection Council, 2009. R-29148 is described, for example by P.B. Goldsbrough et al., Plant Physiology, (2002), Vol. 130 pp. 1497-1505 and references therein, PPG-1292 is known from WO 2009/21 1761 and N-(2- methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide is known from EP365484. Especially preferably, the safener comprises (e.g. is) benoxacor, cloquintocet-mexyl, cloquintocet acid, cyprosulfamide, mefenpyr-diethyl or N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide, or an agrochemically acceptable salt of any of these. Most preferably, the safener is cloquintocet-mexyl or cloquintocet acid. In the above-mentioned mixtures of compounds of formula I, in particular a compound selected from said Tables 1 to 333 and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14 as disclosed or illustrated herein, with one or more further herbicides, and/or with a safener, the weight mixing of the compound of formula I to any further herbicide and/or the mixing ratio of the compound of formula I to a safener, can vary over a large range and are, preferably, 200:1 to 1 :200, especially 50:1 to 1 :50, more especially 20:1 to 1 :20, even more especially 10:1 to 1 :10. These weight ratios are measured as the salt-fee

compounds.

The rate of application of safener relative to the herbicide is largely dependent upon the mode of application. In the case of field treatment, generally from 1 to 1000 g of safener/ha, preferably from 2 to 500 g or from 10 to 200 g/ha of safener/ha, and generally from 10 to 10000 g of total herbicide/ha, preferably from 50 to 3000 or from 100 to 1500 g of total herbicide / ha, are applied; all measured as the salt-fee compounds. The herbicidal compositions according to the invention are suitable for all methods of application customary in agriculture, such as, for example, pre-emergence application, post-emergence application and seed dressing. Depending upon the intended use, the safeners can be used for pretreating the seed material of the crop plant (dressing the seed or seedlings) or introduced into the soil before or after sowing, followed by the application of the (unsafened) compound of the formula (I), optionally in combination with a co- herbicide. It can, however, also be applied alone or together with the herbicide before or after emergence of the plants. The treatment of the plants or the seed material with the safener can therefore take place in principle independently of the time of application of the herbicide. The treatment of the plant by simultaneous application of herbicide and safener (e.g. in the form of a tank mixture) is generally preferred. The rate of application of safener relative to herbicide is largely dependent upon the mode of application. In the case of field treatment, generally from 0.001 to 5.0 kg of safener/ha, preferably from 0.001 to 0.5 kg of safener/ha, are applied (measured as the salt-fee compound). In the case of seed dressing, generally from 0.001 to 10 g of safener/kg of seed, preferably from 0.05 to 2 g of safener/kg of seed, are applied (measured as the salt-fee compounds). When the safener is applied in liquid form, with seed soaking, shortly before sowing, it is advantageous to use safener solutions which contain the active ingredient in a concentration of from 1 to 10 000 ppm, preferably from 100 to 1000 ppm (measured as the salt-fee compounds). It is preferred to apply the compound of formula (I), and/or one or more further herbicides, together with one of the safeners mentioned above. A compound of formula I may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers, and more particularly ammonium nitrate and/or urea fertilizers). Suitable formulation types include granules of fertiliser. The mixtures suitably contain up to 25% by weight of the compound of formula I.

The invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula I.

Examples of active ingredients which optionally can be combined / mixed with a compound of formula I include the following: a plant activator selected from the group of substances consisting of acibenzolar (6) + COMPOUND OF FORMULA I, acibenzolar-S-methyl (6) + COMPOUND OF FORMULA I, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + COMPOUND OF FORMULA I,

or

a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)- ethyl piperonylate (lUPAC name) (934) + COMPOUND OF FORMULA I, 5-(1 ,3- benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + COMPOUND OF FORMULA I, farnesol with nerolidol (alternative name) (324) + COMPOUND OF

FORMULA I, MB-599 (development code) (498) + COMPOUND OF FORMULA I, MGK 264 (development code) (296) + COMPOUND OF FORMULA I, piperonyl butoxide (649) + COMPOUND OF FORMULA I, piprotal (1343) + COMPOUND OF FORMULA I, propyl isomer (1358) + COMPOUND OF FORMULA I, S421 (development code) (724) + COMPOUND OF FORMULA I, sesamex (1393) + COMPOUND OF FORMULA I, sesasmolin (1394) and sulfoxide (1406) + COMPOUND OF FORMULA I.

The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts (CAS) Registry number. The above described mixing partners are known. Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound

"abamectin" is described under entry number (1 ). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound

"acetoprole" is described under the internet address

http://www.alanwood.net/pesticides/acetoprole.htmL.

Most of the active ingredients described above are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular compound; in that case, the lUPAC name, the lUPAC/Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "develoment code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed. "CAS Reg. No" means the Chemical Abstracts Registry Number.

The compounds of formula I according to the invention can also be used in combination with one or more other synergists. In particular, the following mixtures of the COMPOUND OF FORMULA I, where this term preferably refers to a compound selected from one of the Tables 1 to 333 (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14), are important: COMPOUND OF FORMULA I + piperonyl butoxide, COMPOUND OF FORMULA I + sesamex, COMPOUND OF FORMULA I + safroxan and COMPOUND OF FORMULA I + dodecyl imidazole.

The mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient" relates to the respective mixture of compound of formula I with the mixing partner).

Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.

The mixtures comprising a compound of formula I selected from Tables 1 to 333 (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14), and one or more active ingredients as described above, can be applied, for example, in a single "ready-mix" form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula I selected from Tables 1 to 333 (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14) and the active ingredients as described above is not essential for working the present invention.

EXAMPLES

The invention is illustrated by the following preparation examples. The ¹H-NMR data of certain compounds of this invention show line broadening at room temperature, suggesting the existence of plural conformational isomers due to, for example keto-enol tautomerism, hindered rotation, ring inversion in the piperidine moitey or nitrogen inversion at the piperidine N-OR center. Broad signals have been labeled with 'br' accordingly.

REFERENCE EXAMPLE 2: Preparation of 3-(2,4-Dimethyl-6-vinyl-phenyl)-4-hvdroxy-8- methoxy-1 ,8-diaza-spiro[4.51dec-3-en-2-one (reference compound P2.3)

Step 1 : Preparation of 4-[2-(2,4-Dimethyl-6-vinyl-phenyl)-acetylamino]-1 -methoxy- piperidine-4-carboxylic acid methyl ester (compound P3.3)

To a solution of 4-amino-1 -methoxy-piperidine-4-carboxylic acid methyl ester (600 mg, 3.03 mmol), triethylamine (1 .05 ml, 763 mg, 7.54 mmol) and 4-dimethylaminopyridine (DMAP, 4 mg) in tetrahydrofuran (20 ml) at 0-5°C was added a solution of (2,4-dimethyl-6-vinyl- phenyl)-acetyl chloride (630 mg, 3.03 mmol) in THF (2 ml) dropwise over 1 hour. The reaction mixture was stirred at 0-5°C for 15 minutes, then at room temperature overnight. The mixture was concentrated in vacuo, diluted with ethyl acetate and water, the layers separated, the aqueous phase extracted once with ethyl acetate, the combined organic phases washed with brine, dried over sodium sulfate and concentrated. The solid residue was suspended in hexane, stirred at room temperature, filtered and dried. Yield: 950 mg of 4-[2-(2,4-dimethyl-6-vinyl-phenyl)-acetylamino]-1 -methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.3) as a solid, mp 142-144°C.

¹H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.27 (s, 6H), 3.50 (s, 3H), 3.63 (s, 3H), 3.69 (s, 2H), 5.28 (dd, J = 1 1 .0, 1 .2 Hz, 1 H), 5.57 (dd, J = 17.2, 1 .2 Hz, 1 H), 6.94 (s, 1 H), 6.98 (m, 1 H), 7.14 (s, 1 H).

LC/MS (ES+): 361 (M+H)⁺ Step 2: Preparation of 3-(2,4-Dimethyl-6-vinyl-phenyl)-4-hydroxy-8-methoxy-1 ,8-diaza- spiro[4.5]dec-3-en-2-one (reference compound P2.3)

To a solution of 4-[2-(2,4-dimethyl-6-vinyl-phenyl)-acetylamino]-1 -methoxy-piperidine-4- carboxylic acid methyl ester (500 mg, 1 .39 mmol) in dimethylformamide (20 ml) at 0°C was added sodium methoxide (225 mg, 4.16 mmol) in one portion and stirring continued at 10°C for 30 minutes, then at room temperature overnight. The reaction mixture was poured on ice and saturated aqueous ammonium chloride, acidified to pH 5-6 with 6N HCI and thoroughly extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, concentrated and dried in vacuo. The residue was purified by chromatography on silica gel (ethyl acetate). Yield: 280 mg of 3-(2,4-dimethyl-6-vinyl- phenyl)-4-hydroxy-8-methoxy-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (reference compound P2.3) as a white solid, mp 198-200°C.

¹H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.13 (s, 3H), 2.31 (s, 3H), 3.56 (br s, 3H), 5.14 (dd, J = 1 1 .1 , 1 .4 Hz, 1 H), 5.64 (dd, J = 17.5, 1 .4 Hz, 1 H), 6.64 (dd, J = 17.5, 1 1 .1 Hz, 1 H), 7.02 (s, 1 H), 7.29 (s, 1 H).

LC/MS (ES+): 329 (M+H)⁺

REFERENCE EXAMPLE 3: Preparation of 3-(2,4-Dimethyl-6-vinyl-phenyl)-4-hvdroxy-8- methoxy-1 -methyl-1 ,8-diaza-spiro[4.51dec-3-en-2-one (reference compound P2.4) Step 1 : Preparation of N-(4-Cyano-1 -methoxy-piperidin-4-yl)-2-(2,4-dimethyl-6-vinyl- phenyl)-N-methyl-acetamide (compound P3.4)

To a solution of 1 -methoxy-4-methylamino-piperidine-4-carbonitrile (600 mg, 3.55 mmol) in pyridine (20 ml) was added (2,4-dimethyl-6-vinyl-phenyl)-acetyl chloride (814 mg, 3.90 mmol) dropwise at 0°C. The reaction mixture was stirred at 0°C for one hour and at room temperature overnight, poured on ice water and acidified to pH 7 with an aqueous 2N HCI solution. The resulting thick precipitate was filtered, washed with cold water, dissolved in ethyl acetate, dried over sodium sulfate and concentrated. The solid residue was suspended in hexane, stirred at room temperature, filtered and dried. Yield: 1 .0 g of N-(4- cyano-1 -methoxy-piperidin-4-yl)-2-(2,4-dimethyl-6-vinyl-phenyl)-N-methyl-acetamide (compound P3.4) as a pale yellow solid, mp 148-151 °C.

1H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.19 (s, 3H), 2.27 (s, 3H), 3.16 (s, 3H), 3.51 (s, 3H), 3.84 (s, 2H), 5.25 (dd, J = 1 1 .0, 1 .5 Hz, 1 H), 5.53 (dd, J = 17.2, 1 .5 Hz, 1 H), 6.83 (dd, J = 17.2, 1 1 .0 Hz, 1 H), 6.94 (s, 1 H), 7.12 (s, 1 H).

LC/MS (ES+): 342 (M+H)⁺ Step 2: Preparation of 4-{[2-(2,4-Dimethyl-6-vinyl-phenyl)-acetyl]-methyl-amino}-1 - methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.5)

To a suspension of N-(4-cyano-1 -methoxy-piperidin-4-yl)-2-(2,4-dimethyl-6-vinyl-phenyl)-N- methyl-acetamide (990 mg, 2.90 mmol) in methanol (2 ml) at 15-20°C was added concentrated sulfuric acid (0.773 ml, 1 .42 g, 14.50 mmol) dropwise over 5 minutes and the reaction mixture was stirred at room temperature overnight. The mixture was poured on ice (20 g), stirred for one hour, then neutralised carefully with 30% aqueous sodium hydroxide to pH 5 (external ice cooling). The thick suspension was filtered, the solid residue washed with cold water, dissolved in dichloromethane, dried over sodium sulfate and concentrated. Yield: 900 mg of 4-{[2-(2,4-dimethyl-6-vinyl-phenyl)-acetyl]-methyl-amino}-1 -methoxy- piperidine-4-carboxylic acid methyl ester (compound P3.5) as a pale yellow solid, mp 160- 162°C.

1H-NMR (400 MHz, CD₃OD): δ 1 .99 (br m, 2H), 2.16 (s, 3H), 2.26 (s, 3H), 2.34 (br m, 2H), 2.78 (br m, 1 H), 2.91 (br m, 1 H), 3.18 (br s, 3H), 3.26 (br m, 2H), 3.50 (s, 3H), 3.59 (s, 3H), 3.78 (br s, 2H), 5.24 (dd, J = 1 1 .0, 1 .5 Hz, 1 H), 5.51 (dd, J = 17.2, 1 .5 Hz, 1 H), 6.79 (dd, J = 17.2, 1 1 .0 Hz, 1 H), 6.91 (s, 1 H), 7.10 (s, 1 H).

LC/MS (ES+): 375 (M+H)⁺ Step 3: Preparation of 3-(2,4-Dimethyl-6-vinyl-phenyl)-4-hydroxy-8-methoxy-1 -methyl-1 ,8- diaza-spiro[4.5]dec-3-en-2-one (reference compound P2.4)

To a solution of 4-{[2-(2,4-dimethyl-6-vinyl-phenyl)-acetyl]-methyl-amino}-1 -methoxy- piperidine-4-carboxylic acid methyl ester (900 mg, 2.40 mmol) in dimethylformamide (10 ml) at 0°C was added sodium methoxide (389 mg, 7.21 mmol) in two portions and stirring continued at 0°C for 1 hour. The reaction mixture was concentrated in vacuo, poured on cold water (25 ml), acidified to pH 5-6 with 6N HCI, the thick suspension was filtered and washed with cold water (3x 20 ml), the solid residue dissolved in ethyl acetate, dried over sodium sulfate and concentrated to yield a first crop of product (400 mg). Further extraction of the aqueous layer, which was saturated with sodium chloride, with ethyl acetate delivered another 390 mg of product after washing with brine, drying over sodium sulfate, and concentration. Yield: 790 mg of 3-(2,4-dimethyl-6-vinyl-phenyl)-4-hydroxy-8- methoxy-1 -methyl-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (reference compound P2.4) as a tan- white solid, mp 158-161 °C.

¹H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.12 (s, 3H), 2.32 (s, 3H), 2.88 (br signal, 3H), 3.55 (s, 3H), 5.14 (dd, J = 1 1 .0, 1 .5 Hz, 1 H), 5.64 (dd, J = 17.2, 1 .5 Hz, 1 H), 6.62 (dd, J = 17.2, 1 1 .0 Hz, 1 H), 7.02 (s, 1 H), 7.30 (s, 1 H).

LC/MS (ES+): 343 (M+H)⁺

REFERENCE EXAMPLE 5: Preparation of 3-(2,4-dimethyl-6-vinyl-phenyl)-4-hvdroxy-8- methoxy-1 -(tetrahvdro-furan-2-yloxy)-1 ,8-diaza-spiro[4.51dec-3-en-2-one (reference compound P2.5) and Carbonic acid 3-(2,4-dimethyl-6-vinyl-phenyl)-8-methoxy-2-oxo-1 - (tetrahydro-furan-2-yloxy)-1 ,8-diaza-spiro[4.51dec-3-en-4-yl ester ethyl ester (reference compound P1 .5) Step 1 : Preparation of 4-{[2-(2,4-Dimethyl-6-vinyl-phenyl)-acetyl]-hydroxy- methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.6)

To a solution of 4-hydroxyamino-1 -methoxy-piperidine-4-carboxylic acid methyl ester (800 mg, 3.92 mmol) in tetrahydrofuran (25 ml) at 0°C was added sodium hydrogen carbonate (560 mg, 6.66 mmol), followed by a solution of (2,4-dimethyl-6-vinyl-phenyl)-acetyl chloride (860 mg, 4.12 mmol) in tetrahydrofuran (2 ml) dropwise. The reaction mixture was stirred at 0°C for one hour and at room temperature overnight. The solvent was evaporated, the residue suspended in water (25 ml), filtered and the solid washed with water (3x 20 ml). The solid material was dissolved in ethyl acetate, dried over sodium sulfate, concentrated and the residue suspended in diethyl ether, stirred at room temperature, filtered and dried. Yield: 1 .0 g of 4-{[2-(2,4-dimethyl-6-vinyl-phenyl)-acetyl]-hydroxy-amino}-1 -methoxy- piperidine-4-carboxylic acid methyl ester (compound P3.6) as a white solid, mp 177-179°C. ¹H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.19 (br s, 3H), 2.26 (s, 3H), 3.52 (br s, 3H), 3.64 (s, 3H), 3.91 (br signal, 2H), 5.24 (dd, J = 1 1 .0, 1 .5 Hz, 1 H), 5.54 (dd, J = 17.3, 1 .4 Hz, 1 H), 6.85 (br m, 1 H), 6.92 (s, 1 H), 7.12 (s, 1 H).

LC/MS (ES+): 377 (M+H)⁺

Step 2: Preparation of 4-[[2-(2,4-Dimethyl-6-vinyl-phenyl)-acetyl]-(tetrahydro-furan-2-yloxy) -amino]-1 -methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.7)

To a solution of 4-{[2-(2,4-dimethyl-6-vinyl-phenyl)-acetyl]-hydroxy-amino}-1 -methoxy- piperidine-4-carboxylic acid methyl ester (1 .0 g, 2.66 mmol) in dichloromethane (25 ml) was added 2,3-dihydro-furan (0.402 ml, 372 mg, 5.31 mmol) and a catalytic amount of p- toluenesulfonic acid monohydrate (51 mg, 0.27 mmol). The reaction mixture was stirred at reflux overnight and concentrated. The residue was dissolved in hot hexane, filtered, the filtrate concentrated and dried in vacuo. Yield: 1.10 g of 4-[[2-(2,4-dimethyl-6-vinyl-phenyl)- acetyl]-(tetrahydro-furan-2-yloxy)-amino]-1 -methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.7) as a gum. This material was used without further purification in the next step.

¹H-NMR (CD₃OD): δ 2.21 (br s, 3H), 2.29 (s, 3H), 3.54 (s, 3H), 3.67 (br s, 3H), 3.86 (br signal, 2H), 4.03 (m, 1 H), 4.12 (m, 1 H), 5.12 (m, 1 H), 5.27 (d, J = 1 1 .0 Hz, 1 H), 5.58 (dd, J = 17.4, 1 .6 Hz, 1 H), 6.86 (br m, 1 H), 6.95 (s, 1 H), 7.16 (s, 1 H).

LC/MS (ES+): 447 (M+H)⁺

Step 3: Preparation of 3-(2,4-Dimethyl-6-vinyl-phenyl)-4-hydroxy-8-methoxy-1 -(tetrahydro- furan-2-yloxy)-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (reference compound P2.5)

To a solution of 4-[[2-(2,4-dimethyl-6-vinyl-phenyl)-acetyl]-(tetrahydro-furan-2-yloxy) -amino]-1 -methoxy-piperidine-4-carboxylic acid methyl ester (1 .0 g, 2.24 mmol) in dimethylformamide (30 ml) at 0°C was added sodium methoxide (363 mg, 6.72 mmol) in four portions and stirring continued at 10°C for 30 minutes, then at room temperature overnight. The reaction mixture was poured on cold saturated aqueous ammonium chloride, the pH adjusted to 6 with 2N HCI and the aqueous phase thoroughly extracted with ethyl acetate (4x 50 ml). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 2:1 ). Yield: 320 mg of 3-(2,4-dimethyl-6-vinyl-phenyl)- 4-hydroxy-8-methoxy-1 -(tetrahydro-furan-2-yloxy)-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (reference compound P2.5) as a solid, mp 132-135°C. ¹H-NMR (CD₃OD): δ 2.16 (s, 3H), 2.35 (s, 3H), 3.58 (s, 3H), 3.98 (m, 1 H), 4.20 (m, 1 H), 5.20 (dd, J = 1 1 .0, 1 .3 Hz, 1 H), 5.59 (br m, 1 H), 5.69 (m, 1 H), 6.65 (dd, J = 17.6, 1 1 .0 Hz, 1 H), 7.06 (s, 1 H), 7.33 (s, 1 H).

LC/MS (ES+): 415 (M+H)⁺

Step 4: Preparation of Carbonic acid 3-(2,4-dimethyl-6-vinyl-phenyl)-8-methoxy-2-oxo-1 - (tetrahydro-furan-2-yloxy)-1 ,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester (reference compound P1 .5)

To a solution of 3-(2,4-dimethyl-6-vinyl-phenyl)-4-hydroxy-8-methoxy-1 -(tetrahydro-furan-2- yloxy)-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (220 mg, 0.53 mmol), triethylamine (0.15 ml, 109 mg, 1 .06 mmol) and a catalytic amount of 4-dimethylaminopyridine in tetrahydrofuran (15 ml) at 0°C was added ethyl chloroformate (0.06 ml, 68 mg, 0.58 mmol) dropwise. The suspension was stirred at 0°C for one hour. The reaction mixture was evaporated, diluted with ethyl acetate and water, the layers separated, the aqueous phase extracted with ethyl acetate (2x 50 ml), the combined organic layers washed with water, brine, dried over sodium sulfate and concentrated. The oily residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :1 ). Yield: 204 mg of carbonic acid 3-(2,4-dimethyl-6- vinyl-phenyl)-8-methoxy-2-oxo-1 -(tetrahydro-furan-2-yloxy)-1 ,8-diaza-spiro[4.5]dec-3-en-4- yl ester ethyl ester (title compound P1 .5) as a colorless gum.

¹H-NMR (400 MHz, CD₃OD, selected signals only): δ 1 .03 (t, 3H), 2.17 (appar d, 3H), 2.32 (s, 3H), 3.55 (s, 3H), 3.93-4.05 (m, 3H), 4.19 (m, 1 H), 5.20 (dd, J = 1 1 .0, 1 .4 Hz, 1 H), 5.65 (m, 2H), 6.58 (m, 1 H), 7.01 (s, 1 H), 7.26 (s, 1 H).

LC/MS (ES+): 487 (M+H)⁺ EXAMPLE 6: Preparation of (2-Ethvnyl-5-methyl-phenyl)-acetyl chloride

Preparation of (5-Methyl-2-trimethylsilanylethynyl-phenyl)-acetic acid

To a solution of (2-iodo-5-methyl-phenyl)-acetic acid (5.5 g, 19.92 mmol) in triethylamine (100 ml) and THF (100 ml) was added copper(l) iodide (152 mg, 0.80 mmol),

bis(triphenylphosphine)palladium(ll) dichloride (280 mg, 0.40 mmol), followed by ethynyltrimethylsilane (3.31 ml, 2.35 g, 23.89 mmol) dropwise at 15°C. The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was diluted with dichloromethane (200 ml), filtered over hyflo (calcined diatomaceous earth) and the filtrate washed (4x 100 ml) with a 5:1 -mixture of water and aqueous 1 N HCI. The organic phase was dried over sodium sulfate, concentrated, and the residue purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :3). Yield: 4.13 g of the title compound (5-methyl-2-trimethylsilanylethynyl-phenyl)-acetic acid as a brownish oil.

1H-NMR (400 MHz, CDCI₃): δ 0.24 (s, 9H), 2.34 (s, 3H), 3.83 (s, 2H), 7.05 (d, J = 7.8 Hz, 1 H), 7.08 (s, 1 H), 7.38 (d, J = 7.8 Hz, 1 H), 1 1 .40 (br s, 1 H).

LC/MS (ES+): 247 (M+H)⁺

Step 2: Preparation of (2-Ethynyl-5-methyl-phenyl)-acetic acid

To a solution of (5-methyl-2-trimethylsilanylethynyl-phenyl)-acetic acid (4.0 g, 16.24 mmol) in methanol (140 ml) at room temperature was added potassium carbonate (4.49 g, 32.49 mmol) in 2 portions. The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was taken up in water and acidified to pH 3 under ice cooling. The resulting precipitate was filtered off, washed twice with cold water, the solid dissolved in dichloromethane, the organic phase dried over sodium sulfate and concentrated. Yield: 2.12 g of the title compound (2-ethynyl-5-methyl-phenyl)-acetic acid as a solid, mp 98-101 °C.

1H-NMR (400 MHz, CDCI₃): δ 2.34 (s, 3H), 3.24 (s, 1 H), 3.85 (s, 2H), 7.07 (d, J = 7.8 Hz, 1 H), 7.10 (s, 1 H), 7.41 (d, J = 7.8 Hz, 1 H), 1 1.10 (br s, 1 H).

LC/MS (ES+): 175 (M+H)⁺

Step 3: Preparation of (2-Ethynyl-5-methyl-phenyl)-acetyl chloride

To a solution of (2-ethynyl-5-methyl-phenyl)-acetic acid (2.12 g, 12.17 mmol) in

dichloromethane (20 ml) at room temperature were added two drops of

dimethylformamide, followed by oxalyl chloride (1 .25 ml, 1 .85 g, 14.58 mmol) dropwise. The reaction mixture was stirred at room temperature, subsequently at 40°C to bring gas evolution to completion, then concentrated under reduced pressure. Yield: 2.20 g of the title compound (2-ethynyl-5-methyl-phenyl)-acetyl chloride as a semi-solid, which fully solidified when kept in the fridge.

1H-NMR (400 MHz, CDCI₃): δ 2.36 (s, 3H), 3.30 (s, 1 H), 4.32 (s, 2H), 7.08 (s, 1 H), 7.12 (d, J = 7.9 Hz, 1 H), 7.44 (d, J = 7.9 Hz, 1 H).

REFERENCE EXAMPLE 7: Preparation of 4-{r2-(2-Ethynyl-5-methyl-phenyl)-acetyll- methoxy-amino)-1 -methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.16)

To a solution of triphenylphosphine (434 mg, 1 .65 mmol) in THF (10 ml) at 0°C was added diisopropyl azodicarboxylate (0.327 ml, 336 mg, 1 .66 mmol) dropwise and the resulting precipitate was stirred at 0°C for 30 minutes. 4-{[2-(2-Ethynyl-5-methyl-phenyl)-acetyl]- hydroxy-amino}-1 -methoxy-piperidine-4-carboxylic acid methyl ester (compound P3.15 obtained by a process analogous to preparation EXAMPLE 5, step 1 ) (470 mg, 1 .30 mmol) in THF (2 ml) was further added dropwise, followed by methanol (0.060 ml, 47.5 mg, 1 .48 mmol) in one portion at 0°C. The reaction mixture was stirred at room temperature for two hours and concentrated in vacuo. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :2). Yield: 186 mg of 4-{[2-(2-ethynyl-5-methyl-phenyl)- acetyl]-methoxy-amino}-1 -methoxy-piperidine-4-carboxylic acid methyl ester (title compound P3.16) as a gum.

1H-NMR (400 MHz, CDCI₃, selected signals only): δ 2.32 (s, 3H), 3.21 (s, 1 H), 3.52 (s, 3H), 3.72 (s, 3H), 3.92 (br signal, total 3H), 7.02 (d, J = 7.7 Hz, 1 H), 7.08 (br s, 1 H), 7.38 (d, J = 7.7 Hz, 1 H).

LC/MS (ES+): 375 (M+H)⁺ EXAMPLE 8: Preparation of 3-(2,6-Dimethyl-4-trimethylsilanylethvnyl-phenyl)-4-hvdroxy-

8-methoxy-1 ,8-diaza-spiro[4.51dec-3-en-2-one

To a solution of 4-hydroxy-3-(4-iodo-2,6-dimethyl-phenyl)-8-methoxy-1 ,8-diaza- spiro[4.5]dec-3-en-2-one (740 mg, 1 .728 mmol) in triethylamine (10 ml) and THF (10 ml) was added copper(l) iodide (13 mg, 0.068 mmol), bis(triphenylphosphine)palladium(ll) dichloride (24 mg, 0.034 mmol), followed by ethynyltrimethylsilane (0.287 ml, 203.5 mg, 2.072 mmol) dropwise at 10°C. The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was diluted with dichloromethane (50 ml), filtered over hyflo (calcined diatomaceous earth) and the filtrate washed (4x) with an aqueous solution of pH 5-6. The organic phase was dried over sodium sulfate,

concentrated, and the residue purified by chromatography on silica gel (ethyl acetate). Yield: 243 mg of the title compound 3-(2,6-dimethyl-4-trimethylsilanylethynyl-phenyl)-4- hydroxy-8-methoxy-1 ,8-diaza-spiro[4.5]dec-3-en-2-one as a tan solid, mp >240°C.

¹H-NMR (400 MHz, CDCI₃, selected signals only): δ 0.24 (s, 9H), 2.10 (s, 6H), 3.56 (br s, 3H), 5.76 (br s, 1 H), 7.17 (s, 2H). LC/MS (ES+): 399 (M+H)⁺

EXAMPLE 9: Preparation of 3-(4-Ethvnyl-2,6-dimethyl-phenyl)-4-hvdroxy-8-methoxy-1 - methyl-1 ,8-diaza-spiro[4.51dec-3-en-2-one (compound P2.12)

To a solution of 3-(2,6-dimethyl-4-trimethylsilanylethynyl-phenyl)-4-hydroxy-8-methoxy- 1 -methyl-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (obtained in analogy to preparation EXAMPLE 8) (167 mg, 0.405 mmol) in methanol (5 ml) at room temperature was added potassium carbonate (1 12 mg, 0.810 mmol) in 2 portions. The reaction mixture was stirred at room temperature for 2.5 hours and concentrated under reduced pressure. The residue was taken up in water and acidified with a 1 N HCI solution to pH 6 under ice cooling. The resulting precipitate was filtered off, the solid suspended in hexane, filtered and the beige solid dried over phosphorus pentoxide under vacuum at 40°C overnight. Yield: 107 mg of 3-(4-ethynyl-2,6-dimethyl-phenyl)-4-hydroxy-8-methoxy-1 -methyl-1 ,8-diaza-spiro[4.5]dec-3- en-2-one (title compound P2.12) as a beige solid, mp 258-260°C.

1H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.14 (s, 6H), 2.89 (br signal, total 3H), 3.41 (s, 1 H), 3.55 (s, 3H), 7.20 (s, 2H).

LC/MS (ES+): 341 (M+H)⁺

EXAMPLE 10: Preparation of 3-(2,6-Dimethyl-4-prop-1 -ynyl-phenyl)-4-hydroxy-8- methoxy-1 -methyl-1 ,8-diaza-spiro[4.51dec-3-en-2-one (compound P2.13)

Propyne was bubbled into a suspension of 4-hydroxy-3-(4-iodo-2,6-dimethyl-phenyl)-8- methoxy-1 -methyl-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (300 mg, 0.678 mmol), copper(l) iodide (13 mg, 0.068 mmol) and bis(triphenylphosphine)palladium(ll) dichloride (24 mg, 0.034 mmol) in triethylamine (20 ml) until saturation, leading to brown coloration of the reaction mixture. This mixture was stirred under the remaining propyne atmosphere at room temperature overnight, diluted with saturated aqueous ammonium chloride (20 ml), the layers separated, the aqueous phase extracted with ethyl acetate (3x 25 ml), the combined organic layers washed with brine, dried over sodium sulfate and concentrated. The gummy brownish residue was triturated with diethyl ether, filtered, dried, concentrated and the solid redissolved in dichloromethane, treated with active charcoal, filtered and concentrated in vacuo to afford a first crop of product (120 mg). The mother liquor was concentrated and purified by chromatography on silica gel (ethyl acetate) to further afford 55 mg of product. Yield: 175 mg of 3-(2,6-dimethyl-4-prop-1 -ynyl-phenyl)-4-hydroxy-8- methoxy-1 -methyl-1 ,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2.13) as a tan solid, mp >240°C.

¹H-NMR (400 MHz, CD₃OD, selected signals only): δ 2.00 (s, 3H), 2.1 1 (s, 6H), 2.88 (br signal, total 3H), 3.55 (s, 3H), 7.08 (s, 2H).

LC/MS (ES+): 355 (M+H)⁺

Compounds of the formula I from Table P1 , compounds of the formula II from Table P2 and intermediates listed in Table P3 can be prepared by analogous procedures. Either one of the following LC-MS methods was used to characterize the compounds:

Method A

MS: ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer);

lonisation method: Electrospray; Polarity: positive/negative ions; Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 100, Desolvation Temperature (°C) 250, Cone Gas Flow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 400; Mass range: 150 to 1000 or 100 to 900 Da.

LC: HP 1 100 HPLC from Agilent: solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column compartment and diode-array detector. Column: Phenomenex Gemini C18, 3 μηι particle size, 1 10 Angstrom, 30 x 3 mm, Temp: 60°C; DAD Wavelength range (nm): 200 to 500; Solvent gradient: A = water + 0.05% v/v HCOOH, B=

Acetonitril/Methanol (4:1 , v/v) + 0.04% v/v HCOOH.

Time (min) A% B% Flow (ml/min)

0.00 95.0 5.0 1 .700

2.00 0.0 100.0 1 .700

2.80 0.0 100.0 1 .700

2.90 95.0 5.0 1 .700

3.00 95.0 5.0 1 .700 Method B

MS: ZMD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) ; lonisation method: Electrospray; Polarity: positive/negative ions; Capillary (kV) 3.80, Cone (V) 30.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Cone Gas Flow (L/Hr) OFF, Desolvation Gas Flow (L/Hr) 600; Mass range: 150 to 1000 (100 to 1500 for LowMass) or 100 to 900 Da.

LC: HP 1 100 HPLC from Agilent: solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Phenomenex Gemini C18, 3 μηη particle size, 1 10 Angstrom, 30 x 3 mm, Temp: 60 °C; DAD Wavelength range (nm): 200 to 500; Solvent gradient: A = water + 0.05% v/v HCOOH, B= Acetonitril/Methanol (4:1 , v:v) + 0.04% v/v HCOOH.

Time (min) A% B% Flow (ml/min)

0.00 95.0 5.0 1 .700

2.00 0.0 100.0 1 .700

2.80 0.0 100.0 1 .700

2.90 95.0 5.0 1 .700

3.00 95.0 5.0 1 .700

Method C

MS: ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer);

lonisation method: Electrospray; Polarity: positive/negative ions; Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 100, Desolvation Temperature (°C) 250, Cone Gas Flow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 400; Mass range: 100 to 900 Da.

LC: HP 1 100 HPLC from Agilent: solvent degasser, quaternary pump (ZCQ), heated column compartment and diode-array detector. Column: Phenomenex Gemini C18, 3 μηη particle size, 30 x 3 mm, Temp: 60°C; DAD Wavelength range (nm): 210 to 500; Solvent gradient: A = water + 5% v/v Methanol + 0.05% v/v HCOOH, B= Acetonitril + 0.05% v/v HCOOH.

Time (min) A% B% Flow (ml/min)

0.00 100 0 1 .700

2.00 0 100 1 .700

2.80 0 100 1 .700

2.90 100 0 1 .700

3.00 100 0 1 .700 The characteristic values obtained for each compound were the retention time ("R_t", recorded in minutes) and the molecular ion as listed in Table P1 , Table P2 and in Table P3.

Table P1 : Physical data of compounds of formula I:

Table P2: Physical data of compounds of formula II:

Table P3: Physical data of intermediates of formula IV or XI:

Compound Structures Melting Point MS/NMR No.

P3.16

LC/MS: 375 (M+H)⁺ (reference X ) X N-0 gum

R_t = 1 .75 min compound) / /

EXAMPLE 7

FORMULATION EXAMPLES

(% = percent by weight)

Example F1 : Emulsion concentrates a) b) c)

Active ingredient 25 % 40 % 50 %

Calcium dodecylbenzenesulfonate 5 % 8 % 6 %

Castor oil polyethylene glycol ether (36 mol of EO) 5 % - -

Tributylphenoxypolyethylene glycol ether (30 mol of EO) - 12 % 4 %

Cyclohexanone - 15 % 20 %

Xylene mixture 65 % 25 % 20 %

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

Example F2: Solutions a) b) c) d)

Active ingredient 80 % 10 % 5 % 95 %

Ethylene glycol monomethyl ether 20 % - - -

Polyethylene glycol MW 400 70 % - -

N-Methylpyrrolid-2-one 20 % - -

Epoxidized coconut oil - 1 % 5 %

Petroleum ether (boiling range: 160-190°) - 94 % -

The solutions are suitable for use in the form of microdrops.

Example F3: Granules a) b) c) d)

Active ingredient 5 % 10 % 8 % 21 % Kaolin 94 % - 79 % 54 %

Highly disperse silica 1 % - 13 % 7 %

Attapulgite - 90 % - 18 % The active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier(s), and the solvent is subsequently evaporated in vacuo.

Example F4: Dusts a) b)

Active ingredient 2 % 5 %

Highly disperse silica 1 % 5 %

Talc 97 % -

Kaolin - 90 %

Ready-to-use dusts are obtained by intimately mixing the carriers and the active ingredient.

Example F5: Wettable powders a) b) c)

Active ingredient 25 % 50 % 75 %

Sodium lignosulfonate 5 % 5 %

Sodium lauryl sulfate 3 % - 5 %

Sodium diisobutylnaphthalenesulfonate - 6 % 10 %

Octylphenoxypolyethylene glycol

ether (7-8 mol of EO) - 2 % -

Highly disperse silica 5 % 10 % 10 %

Kaolin 62 % 27 % -

The active ingredient is mixed with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders, which can be diluted with water to give suspensions of any desired concentration. Example F6: Extruder granules

Active ingredient 10 %

Sodium lignosulfonate 2 %

Carboxymethylcellulose 1 %

Kaolin 87 % The active ingredient is mixed with the additives, and the mixture is ground, moistened with water, extruded, granulated and dried in a stream of air.

Example F7: Coated granules

Active ingredient 3 %

Polyethylene glycol (MW 200) 3 %

Kaolin 94 %

In a mixer, the finely ground active ingredient is applied uniformLy to the kaolin, which has been moistened with the polyethylene glycol. This gives dust-free coated granules.

Example F8a: Suspension concentrate

Active ingredient 40 %

Ethylene glycol 10 %

Nonylphenoxypolyethylene glycol ether (15 mol of EO) 6 %

Sodium lignosulfonate 10 %

Carboxymethylcellulose 1 %

37 % aqueous formaldehyde solution 0.2 %

Silicone oil (75 % aqueous emulsion) 0.8 %

Water 32 %

Example F8b: Suspension concentrate

Active ingredient 10%

Naphthalenesulfonic acid, sodium salt condensed with formaldehyde 2%

Solution of an acrylic graft copolymer in water and propyleneglycole 8%

Silicone antifoam emulsion 0.5%

DL-propanediol-(1 ,2) 3%

Heteropolysaccharide 0.5%

1 ,2-Benzisothiazol-3-one 0.2%

Water 75.8%

The finely ground active ingredient is mixed intimately with the additives. Suspensions of any desired concentration can be prepared from the thus resulting suspension concentrate by dilution with water. Example F9: Powders for dry seed treatment a) b) c) active ingredient 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % -

Kaolin 65 % 40 % -

Talcum 20 %

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Example F10: Flowable concentrate for seed treatment

active ingredient

propylene glycol

copolymer butanol PO/EO

tristyrenephenole with 10-20 moles EO

1 ,2-benzisothiazolin-3-one (in the form of a 20% solution

water)

monoazo-pigment calcium salt

Silicone oil (in the form of a 75 % emulsion in water)

Water

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Example F1 1 a: Oil-based suspension concentrate (based on a vegetable

Active ingredient 10%

Tristyrylphenole with 16 moles EO 10%

Block copolymer of polyhydroxystearic acid and polyalkylene glycols 2%

AEROSIL 200 1 %

Rape seed oil methyl ester 12%

Oleic acid 65% Example F1 1 b: Oil-based suspension concentrate (based on a mineral oil)

Active ingredient 10%

Ethoxylated alcohols, C16-18 and C18-unsatd 5%

Dodecyl-benzene sulfonic acid Ca-salt linear 2.5%

2-Pyrrolidinone, 1 -ethenylhexadecyl-, homopolymer 1 %

Organophilic clay 1 %

Mixture of petroleum 80.5% The finely ground active ingredient is mixed intimately with the additives. Suspensions of any desired concentration can be prepared from the thus resulting suspension concentrate by dilution with water.

Preferably, the term "active ingredient" used above refers to one of the compounds selected from Tables 1 to 333 shown above (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14). It also refers to mixtures of the compound of formula I, in particular a compound selected from said Tables 1 to 333 (and/or one of compounds P1 .7 to P1 .15 or P2.7 to P2.14), with one or more further herbicides and/or a safener, which mixtures are specifically disclosed herein.

BIOLOGICAL EXAMPLES

The following Biological Examples illustrate the herbicidal properties of certain compounds of formula (I) exemplified herein.

Biological Example 1 - Glasshouse screen no. 1 for Herbicidal activity

Compounds were tested for either pre- or post-emergence herbicidal activity against four weed species, as shown below. The compounds were applied at 1000g/ha and 460L/ha and the plants were then stored in the glasshouse for 12 days at 24 °C, 14 hours daylight. Scores were given as percentage phytotoxicity on the particular weed species, assessed visually, where complete control of the target is 100 and 0 is no control.

Test species Treatment timing Rate (g/ha)

Amaranthus retroflexus

Pre - or post- emergence 1000

(AMARE)

Lolium perenne (LOLPE) Pre - or post- emergence 1000

Stellaria media (STEME) Pre - or post- emergence 1000

Digitaria sanguinalis (DIGSA) Pre - or post- emergence 1000

AMARE and STEME are broadleaved weed species.

LOLPE is a "cool-season" grassy weed species.

DIGSA is a "warm-season" grassy weed species.

The results (% phytoxicity) of performing Biological Example 1 using certain compound exemplified herein are shown below.

Biological Example 1 - Post-emergence herbicidal data

Compound AMARE LOLPE STEME DIGSA

number

P1 .3 10 80 60 80

P1 .4 0 50 40 0

P1 .7 60 80 90 90 P1.8 50 60 70 60

P1.9 40 70 50 60

P1.10 0 40 0 70

P1.12 30 70 20 80

P1.13 0 40 0 50

P1.14 70 80 60 90

P2.3 0 70 50 80

P2.5 0 20 0 30

P2.6 50 70 80 80

P2.7 50 60 80 70

P2.8 40 60 50 60

P2.9 0 0 0 70

P2.11 60 80 70 90

P2.12 0 0 0 50

P2.13 40 70 60 90

Biological Example 1 - Pre-emergence herbicidal data

Compound AMARE LOLPE STEME DIGSA number

P1.3 0 10 0 60

P1.4 0 0 0 0

P1.7 90 100 90 100

P1.8 40 100 20 100

P1.9 90 100 90 100

P1.10 NC 70 0 10

P1.12 0 100 0 90

P1.13 0 50 0 20

P1.14 60 100 20 100 P2.3 0 20 0 0

P2.5 0 0 0 0

P2.6 90 100 90 100

P2.7 40 100 70 90

P2.8 70 100 90 100

P2.9 0 0 0 20

P2.1 1 90 100 80 100

P2.12 0 0 0 30

P2.13 40 100 50 70

Biological Example 2 - Glasshouse screen no. 2 for Herbicidal activity Seeds of a variety of test species were sown in standard soil in pots. After cultivation for one day (pre-emergence) or after 8 days cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity), the plants were sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS Reg. No. 9005-64-5). The test plants were then grown in a glasshouse under controlled conditions (at 24/16°C, day/night; 14 hours light; 65 % humidity) and watered twice daily. After 13 days for pre- or post-emergence, the test was evaluated visually, and an assessed percentage phytotoxicity score given for each herbicidal application on each plant/weed species (with 100 = total damage to plant; 0 = no damage to plant).

Pre- and post-emergence herbicide application tests using two different selections of weeds follow. Biological Example 2A: Pre-Emergence Herbicidal Activity

Test plants: Alopecurus myosuroides (ALOMY), Setaria faberi (SETFA), Echinochloa crus- galli (ECHCG), Solanum nigrum (SOLNI), Amaranthus retroflexus (AMARE) and Ipomoea hederacea (IPOHE).

Biological Example 2A: Post-Emergence Herbicidal Activity

CompApplicaSOLNI AMARE SETFA ALOMY ECHCG IPOHE ound tion Rate

number (g/ha)

P1 .13 250 0 20 80 80 80 0

P1 .14 250 20 70 90 90 100 10

P2.12 250 0 0 0 0 0 0

P2.13 250 30 40 100 90 100 30 (measure

-ment 1 )

P2.13 250 80 60 90 90 100 20 (measure

-ment 2) Biological Example 2B: Pre-Emergence Herbicidal Activity

Test plants: Lolium perenne (LOLPE), Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), and Avena fatua (AVEFA).

Biological Example 2B: Post-Emergence Herbicidal Activity

Compound Application

number Rate (g/ha) LOLPE ALOMY ECHCG AVEFA

P1 .7 250 100 90 100 100

P1 .12 250 70 90 80 90

P1 .14 250 70 90 100 80

P2.13 250 40 70 90 80

Claims

1 . A method of controlling weeds in crops of useful plants, which comprises applying a compound of the formula I or an agrochemically acceptable salt thereof:

or applying a herbicidal composition comprising such a compound or salt, to the weeds and/or to the plants and/or to the locus thereof; wherein:

Ci_-2fluoroalkoxy, or halogen;

R⁴ is hydrogen, Ci_-4alkyl, C_2-4alkenyl, C_2-4alkynyl, C_3-6cycloalkyl, Ci_-2fluoroalkyl, Ci_-4alkoxy, Ci_-2fluoroalkoxy, halogen; or phenyl or phenyl substituted by 1 , 2 or 3 of, independently, Ci_-3alkyl, Ci_-2fluoroalkyl, Ci_-3alkoxy, Ci_-2fluoroalkoxy, halogen or cyano;

R⁵ is hydrogen or Ci_-2alkyl; or R⁵ is phenyl or phenyl substituted by 1 , 2 or 3 of, independently, Ci_-3alkyl, Ci_-2fluoroalkyl, Ci_-3alkoxy, Ci_-2fluoroalkoxy, halogen or cyano; and R⁶ is hydrogen, Ci_-3alkyl, C_2-3alkenyl, C_2-3alkynyl, cyclopropyl, Ci_-2fluoroalkyl, Ci_-2alkoxy, Ci_-2fluoroalkoxy, or halogen; provided that:

(i) one or both of R² and R⁶ is or are, independently, C_2-3alkynyl; and/or

A is either NR¹ or NOR¹; wherein R¹ is hydrogen, Ci_-6alkyl, Ci_-4fluoroalkyl, C₃-₆cycloalkyl, or C₃-₆cycloalkyl wherein in the cycloalkyl moiety one methylene group is replaced by O, S or NR₀, where R₀ is Ci_-4alkyl or Ci_-4alkoxy;

or R¹ is C₃-₆cycloalkyl(Ci_-3)alkyl-, or C₃-₆cycloalkyl(Ci_-3)alkyl- wherein in the cycloalkyl moiety one methylene group is replaced by O, S or NR₀, where R₀ is Ci_-4alkyl or Ci_-4alkoxy; or R¹ is C₂-₄alkenyl-CH₂-, C₂-₄alkenyl-CH(Me)-, C₂-₃fluoroalkenyl-CH₂-,

independently, Ci-C₃alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, CrC₃alkylsulfonyl, halogen, cyano or by nitro), heteroarylCi-C₈alkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, Ci-C₃ alkylsulfonyl, halogen, cyano or by nitro), C₃-C₈alkenyl, C₃-C₈fluoroalkenyl, C₃-C₈alkynyl, -C(X^a)-R^a, -C(X^b)-X^c-R^b, -C(X^d)-N(R^c)-R^d, -S0₂-R^e, -P(X^e)(R )-R⁹ or -CH₂-X-R^h; wherein X^a, X^b, X^c, X^d, X^e and X are independently of each other oxygen or sulfur; and wherein:

R^a is H, Ci-Ci₈alkyl, C₂-Ci₈alkenyl, C₂-Ci₈alkynyl, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d- Ci₀nitroalkyl, Ci-Ci₀aminoalkyl, Ci-C₅alkylaminoCi-C₅alkyl, C₂-C₈dialkylaminoCi-C₅alkyl, C₃- C₇cycloalkylCi-C₅alkyl, Ci-C₅alkoxyCi-C₅alkyl, C₃-C₅alkenyloxyCi-C₅alkyl, C₃- C₅alkynyloxyCi-C₅alkyl, Ci-C₅alkylthioCi-C₅alkyl, Ci-C₅alkylsulfinylCi-C₅alkyl, C

C₅alkylsulfonylCi-C₅alkyl, C₂-C₈alkylideneaminoxyCi-C₅alkyl, Ci-C₅alkylcarbonylCi-C₅alkyl, Ci-C₅alkoxycarbonylCi-C₅alkyl, aminocarbonylCrC₅alkyl, d-dalkylaminocarbonyld- C₅alkyl, C2-C₈dialkylaminocarbonylCi-C₅alkyl, Ci-C₅alkylcarbonylaminoCi-C₅alkyl, /V-d- C₅alkylcarbonyl-/V-Ci-C₅alkylaminoCi-C₅alkyl, C3-C₆trialkylsilylCi-C₅alkyl, phenylCrC₅alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, CrC₃alkyl, d- dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, d-dcycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1 , 2 or 3 of,

R^b is d-d₈alkyl, d-Ci₈alkenyl [e.g. d-Ci₇alkenyl-CH₂- or C₂-d₆alkenyl-CH(Me)-], d- Ci₈alkynyl [e.g. d-Ci₇alkynyl-CH₂- or C₂-d₆alkynyl-CH(Me)-], d-Ci₀fluoroalkyl, d- Ciocyanoalkyl, d-d₀nitroalkyl, d-Ci₀aminoalkyl, d-dalkylaminod-dalkyl, d- ddialkylaminoCrdalkyl, d-dcycloalkyld-dalkyl, d-dalkoxyd-dalkyl, d- dalkenyloxyd-dalkyl, d-dalkynyloxyd-dalkyl, d-dalkylthiod-dalkyl, d- dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl, d-dalkylideneaminoxyd-dalkyl, d-dalkylcarbonyld-dalkyl, d-dalkoxycarbonyld-dalkyl, aminocarbonyld-dalkyl, d- dalkylaminocarbonylCrdalkyl, d-ddialkylaminocarbonyld-dalkyl, d- dalkylcarbonylaminoCrdalkyl, /V-Ci-dalkylcarbonyl-/V-Ci-dalkylaminoCrdalkyl, d- dtrialkylsilylCrdalkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d- dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld- dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d- dalkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, d-dalkyl-thio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), d-dfluoroalkenyl, d-dcycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d- dalkoxy, Crdfluoroalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-d alkyl, d-₃fluoroalkyl, d-dalkoxy, d- dfluoroalkoxy, halogen, cyano or nitro; and R^c and R^d are each independently of each other hydrogen, Ci-Ci₀alkyl, C₃-Ci₀alkenyl [e.g. C₂-C₉alkenyl-CH₂- or C₂-C₈alkenyl-CH(Me)-], C₃-Ci₀alkynyl [e.g. C₂-C₉alkynyl-CH₂- or C₂-C₈alkynyl-CH(Me)-], C₂-Ci₀fluoroalkyl, Ci-Ciocyanoalkyl, CrCi₀nitroalkyl, C

Cioaminoalkyl, Ci-C₅alkylaminoCi-C₅alkyl, C₂-C₈dialkylaminoCi-C₅alkyl, C₃-C₇cycloalkylCr C₅alkyl, Ci-C₅alkoxyCi-C₅alkyl, C₃-C₅alkenyloxyCi-C₅alkyl, C₃-C₅alkynyloxyCi-C₅alkyl, d- C₅alkylthioCi-C₅alkyl, Ci-C₅alkylsulfinylCi-C₅alkyl, Ci-C₅alkylsulfonylCi-C₅alkyl, C₂- C₈alkylideneaminoxyCi-C₅alkyl, Ci-C₅alkylcarbonylCi-C₅alkyl, d-dalkoxycarbonyld- C₅alkyl, aminocarbonylCi-C₅alkyl, Ci-C₅alkylaminocarbonylCi-C₅alkyl, C₂- C₈dialkylaminocarbonylCi-C₅alkyl, Ci-C₅alkylcarbonylaminoCi-C₅alkyl, /V-d- C₅alkylcarbonyl-/V-C₂-C₅alkylaminoalkyl, C₃-C₆trialkylsilylCi-C₅alkyl, phenylCrC₅alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, d- C₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, d-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-C₃fluoroalkoxy, halogen, cyano or nitro;

heteroarylamino or heteroarylamino substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;

diheteroarylamino or diheteroarylamino substituted by 1 , 2 or 3 of, independently, d- C₃alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro;

phenylamino or phenylamino substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d- C₃fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-C₃fluoroalkoxy, halogen, cyano or by nitro; or C₃-C₇cycloalkylamino, di(d- dcycloalkyl)amino or C₃-C₇cycloalkoxy;

R^e is d-doalkyl, C₂-d₀alkenyl, C₂-d₀alkynyl, d-d₀fluoroalkyl, d-d₀cyanoalkyl, d- Ci₀nitroalkyl, d-Ci₀aminoalkyl, d-dalkylaminod-dalkyl, d-C₈dialkylaminod-dalkyl, C₃- dcycloalkylCrdalkyl, d-dalkoxyd-dalkyl, C₃-C₅alkenyloxyd-C₅alkyl, C₃- C₅alkynyloxyCi-C₅alkyl, Ci-C₅alkylthioCi-C₅alkyl, Ci-C₅alkylsulfinylCi-C₅alkyl, C

C₅alkylsulfonylCi-C₅alkyl, C2-C₈alkylideneaminoxyCi-C₅alkyl, Ci-C₅alkylcarbonylCi-C₅alkyl, Ci-C₅alkoxycarbonylCi-C₅alkyl, aminocarbonylCrC₅alkyl, d-dalkylaminocarbonyld- C₅alkyl, C2-C₈dialkylaminocarbonylCi-C₅alkyl, Ci-C₅alkylcarbonylaminoCi-C₅alkyl, /V-d- C₅alkylcarbonyl-/V-Ci-C₅alkylaminoCi-C₅alkyl, C3-C₆trialkylsilylCi-C₅alkyl, phenylCrC₅alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, CrC₃alkyl, d- C₃fluoroalkyl, CrC₃alkoxy, CrC₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, d- dalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-dalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-C₃fluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, d-d alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or by nitro; heteroarylamino or heteroarylamino substituted by 1 , 2 or 3 of, independently, d-C₃ alkyl, d-dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or by nitro;

phenylamino or phenylamino substituted by 1 , 2 or 3 of, independently, d-dalkyl, d- dfluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1 , 2 or 3 of, independently, d-dalkyl, d-dfluoroalkyl, d- dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; or d-dcycloalkylamino, di(C₃- dcycloalkyl)amino, d-dcycloalkoxy, d-d₀alkoxy, d-d₀fluoroalkoxy, d-dalkylamino or d-ddialkylamino;

R and R⁹ are are each independently of each other d-d₀alkyl, d-Ci₀alkenyl, d- Cioalkynyl, d-Ci₀alkoxy, Ci-Ciofluoroalkyl, Ci-Ciocyanoalkyl, d-d₀nitroalkyl, d- Cioaminoalkyl, d-dalkylaminod-dalkyl, d-ddialkylaminod-dalkyl, d-dcycloalkyld- dalkyl, d-dalkoxyd-dalkyl, d-dalkenyloxyd-dalkyl, d-dalkynyloxyd-dalkyl, d- dalkylthiod-dalkyl, d-dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl, d- dalkylideneaminoxyd-dalkyl, d-dalkylcarbonyld-dalkyl, d-dalkoxycarbonyld- dalkyl, aminocarbonyld-dalkyl, d-dalkylaminocarbonyld-dalkyl, d- ddialkylaminocarbonylCrdalkyl, d-dalkylcarbonylaminoCrdalkyl, /V-d- dalkylcarbonyl-/V-d-dalkylaminoalkyl, d-dtrialkylsilyld-dalkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-dalkyl, d- C₃fluoroalkyl, CrC₃alkoxy, CrC₃fluoroalkoxy, CrC₃alkylthio, CrC₃alkylsulfinyl, d- C₃alkylsulfonyl, halogen, cyano, or by nitro), heteroarylCrC₅alkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, Ci-C₃fluoroalkyl, d- C₃alkoxy, Ci-C₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, CrC₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅fluoroalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, Ci-C₃ alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or by nitro; heteroarylamino or heteroarylamino substituted by 1 , 2 or 3 of, independently, d-d alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or by nitro;

diheteroarylamino or diheteroarylamino substituted by 1 , 2 or 3 of, independently, d-d alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or nitro;

phenylamino or phenylamino substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, d- C₃fluoroalkyl, d-dalkoxy, d-dfluoroalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-C₃fluoroalkoxy, halogen, cyano or nitro; or C₃-C₇cycloalkylamino, di(d- dcycloalkyl)amino, d-dcycloalkoxy, d-d₀fluoroalkoxy, d-dalkylamino or C₂- Csdialkylamino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d- dalkoxy, d-C₃fluoroalkoxy, halogen, cyano or nitro; and

R^h is d-doalkyl, d-doalkenyl [e.g. d-C₉alkenyl-CH₂- or C₂-C₈alkenyl-CH(Me)-], d-doalkynyl [e.g. d-C₉alkynyl-CH₂- or C₂-C₈alkynyl-CH(Me)-], Ci-Ciofluoroalkyl, d- Ciocyanoalkyl, d-Ci₀nitroalkyl, C₂-d₀aminoalkyl, d-dalkylaminod-dalkyl, C₂- Csdialkylaminod-dalkyl, d-dcycloalkyld-dalkyl, d-dalkoxyd-dalkyl, d- dalkenyloxyd-dalkyl, d-dalkynyloxyd-dalkyl, d-dalkylthiod-dalkyl, d- dalkylsulfinyld-dalkyl, d-dalkylsulfonyld-dalkyl, d-C₈alkylideneaminoxyCi-dalkyl, d-dalkylcarbonyld-dalkyl, d-dalkoxycarbonyld-dalkyl, aminocarbonyld-dalkyl, d- dalkylaminocarbonylCrdalkyl, d-C₈dialkylaminocarbonyld-dalkyl, d- dalkylcarbonylaminoCrdalkyl, /V-Ci-dalkylcarbonyl-/V-Ci-dalkylaminoCrdalkyl, C₃- C₆trialkylsilylCi-C₅alkyl, phenyld-dalkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, d-C₃fluoroalkyl, d-dalkoxy, d-C₃fluoroalkoxy, d- dalkylthio, d-dalkylsulfinyl, d-d alkylsulfonyl, halogen, cyano or by nitro), heteroaryld- Csalkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, d- dalkyl, d-C₃fluoroalkyl, d-C₃alkoxy, d-dfluoroalkoxy, d-dalkylthio, d-dalkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), phenoxyCrC₅alkyl (wherein the phenyl is optionally substituted by 1 , 2 or 3 of, independently, d-C₃alkyl, CrC₃fluoroalkyl, d- C₃alkoxy, CrC₃fluoroalkoxy, Ci-C₃alkylthio, CrC₃alkylsulfinyl, C C₃ alkylsulfonyl, halogen, cyano or by nitro), heteroaryloxyCi-C₅alkyl (wherein the heteroaryl is optionally substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, Ci-C₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, Ci-C₃alkylthio, Ci-C₃akylsulfinyl, C C₃ alkylsulfonyl, halogen, cyano or by nitro), C₃- C₅fluoroalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by 1 , 2 or 3 of,

independently, Ci-C₃alkyl, CrC₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen or by nitro; or heteroaryl or heteroaryl substituted by 1 , 2 or 3 of, independently, Ci-C₃alkyl, d- C₃fluoroalkyl, Ci-C₃alkoxy, Ci-C₃fluoroalkoxy, halogen, cyano or by nitro; wherein the term "heteroaryl" means an aromatic ring system containing at least one ring heteroatom and consisting either of a single ring or of two fused rings; and provided that, when R² is methyl or ethyl, R⁴ is methyl, R⁶ is ethynyl, and A is NH, then G is a latentiating group;

and provided that, when R² is methyl or ethyl, R⁴ is ethynyl, R⁶ is methyl, and A is NH, then G is a latentiating group.

2. A method as claimed in claim 1 , wherein the crops of useful plants comprise non-oat cereals, rice, corn, sugarcane, soybean, cotton, rape, sunflower and/or sugarbeet.

3. A method as claimed in claim 2, wherein the crops of useful plants comprise wheat, barley, rye, triticale, rice, corn and/or soybean.

4. A method as claimed in claim 1 , 2 or 3, wherein the weeds to be controlled comprise monocotyledonous weeds.

5. A method as claimed in claim 4, wherein the weeds to be controlled comprise grassy monocotyledonous weeds.

6. A method as claimed in claim 5, wherein the weeds to be controlled comprise weeds from the genus Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Digitaria, Echinochloa, Eriochloa, Leptochloa, Lolium, Monochoria, Panicum, Phalaris, Poa, Rottboellia, Sagittaria, Setaria and/or Sorghum.

7. A method as claimed in claim 5, wherein the weeds to be controlled comprise weeds from the genus Brachiaria, Digitaria, Echinochloa, Eriochloa, Leptochloa, Monochoria,

Panicum, Setaria and/or Sorghum.

8. A method as claimed in claim 5, wherein the weeds to be controlled comprise weeds from the genus Agrostis, Alopecurus, Apera, Avena, Bromus, Lolium and/or Poa.

9. A method as claimed in any of claims 1 to 8, wherein the compound of formula (I) or the salt thereof is applied post-emergence.

10. A method as claimed in any of claims 1 to 9, wherein R is hydrogen, Ci_-4alkyl, Ci_-2fluoroalkyl, Ci_-2cyanoalkyl, C₂-₃alkenyl-CH₂-, C_2-3alkenyl-CH(Me)-,

C_2-3fluoroalkenyl-CH₂-, C₂chloroalkenyl-CH₂-, C_2-3alkynyl-CH₂-, benzyl, Ci_-2alkoxy(Ci_-2)alkyl or Ci_-2alkoxy-CH₂CH₂0-(Ci_-2)alkyl.

1 1 . A method as claimed in any of claims 1 to 9, wherein R is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyanomethyl, trifluoromethyl, 2,2,2-trifluoroethyl, allyl, 3,3-dichloroallyl, propargyl, benzyl, methoxymethyl, ethoxymethyl, methoxyethyl or

(2-methoxy-ethoxy)methyl.

12. A method as claimed in any of claims 1 to 9, wherein R is methyl.

13. A method as claimed in any of claims 1 to 12, wherein A is either NR¹ or NOR¹, wherein

R¹ is hydrogen, Ci_-4alkyl, Ci_-2fluoroalkyl, C₃-₆cycloalkyl, or C_4-6cycloalkyl wherein in the cycloalkyl moiety one methylene group is replaced by O, S or NR₀, wherein R₀ is Ci_-3alkyl or Ci_-3alkoxy,

Ci_-3alkoxy, or R¹ is C₂-3alkenyl-CH₂-, C₂-3alkenyl-CH(Me)-, C₂-3fluoroalkenyl-CH₂-,

Ci_-2alkoxy(Ci_-3)alkyl or Ci_-2alkoxy-CH₂CH₂0-(Ci_-2)alkyl;

14. A method as claimed in any of claims 1 to 12, wherein A is either NR¹ or NOR¹, wherein

R¹ is hydrogen, Ci_-3alkyl, C₃-₆cycloalkyl, or C₅-₆cycloalkyl wherein in the cycloalkyl moiety one methylene group is replaced by O or S,

or R¹ is cyclopropylmethyl-, or C₅-₆cycloalkylmethyl- wherein in the cycloalkyl moiety one methylene group is replaced by O or S,

methoxy-CH₂CH₂0-(Ci_-2)alkyl;

15. A method as claimed in any of claims 1 to 12, wherein A is either NR¹ or NOR¹, wherein R¹ is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, allyl, propargyl or methoxymethyl;

16. A method as claimed in any of claims 1 to 12, wherein A is NR¹, wherein R¹ is hydrogen or methyl;

provided that, when both R⁴ and R⁶ are hydrogen, then R¹ is hydrogen.

17. A method as claimed in any of claims 1 to 16, wherein A is NR¹.

18. A method as claimed in any of claims 1 to 12, wherein A is NR¹ and R¹ is hydrogen.

19. A method as claimed in any of claims 1 to 18, wherein, when G is a latentiating group, then G is -C(X^a)-R^a or -C(X^b)-X^c-R^b, wherein X^a, X^b and X^c are oxygen; R^a is C Ci₀alkyl, C₂-

C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl or Ci-C₄alkoxyCi-C₄alkyl; and R^b is CrCi₀alkyl, C₂-C₅alkenyl-CH₂-, C₂-C₄alkenyl-CH(Me)-, C₂-C₅alkynyl-CH₂-, C₂-C₄alkynyl-CH(Me)-, C₃- C₆cycloalkyl or Ci-C alkoxyCrC alkyl.

20. A method as claimed in any of claims 1 to 19, wherein G is hydrogen, or a latentiating group which is -C(X^a)-R^a or -C(X^b)-X^c-R^b.

21 . A method as claimed in any of claims 1 to 20, wherein R² is methyl, ethyl, vinyl, ethynyl, cyclopropyl, C-ifluoroalkyl, methoxy, Cifluoroalkoxy, fluoro, bromo or chloro.

22. A method as claimed in any of claims 1 to 20, wherein R² is methyl, ethyl or ethynyl.

23. A method as claimed in any of claims 1 to 20, wherein R² is methyl or ethynyl.

24. A method as claimed in any of claims 1 to 23, wherein R⁴ is hydrogen, Ci_-3alkyl, vinyl, (£)-prop-1 -enyl, (Z)-prop-l -enyl, ethynyl, prop-1 -ynyl, Cifluoroalkyl, methoxy,

Cifluoroalkoxy, halogen; or phenyl or phenyl substituted by 1 , 2 or 3 of, independently, methyl, Cifluoroalkyl, methoxy, Cifluoroalkoxy or halogen.

25. A method as claimed in any of claims 1 to 23, wherein R⁴ is hydrogen, Ci_-2alkyl, vinyl, (£)-prop-1 -enyl, (Z)-prop-l -enyl, ethynyl or prop-1 -ynyl.

26. A method as claimed in any of claims 1 to 23, wherein R⁴ is methyl, ethynyl or prop-1 -ynyl.

27. A method as claimed in any of claims 1 to 23, wherein R⁴ is prop-1 -ynyl.

28. A method as claimed in claim 27, wherein R² and R⁶ are methyl.

29. A method as claimed in any of claims 1 to 28, wherein R⁵ is hydrogen or Ci_-2alkyl; or R⁵ is phenyl or phenyl substituted by 1 , 2 or 3 of, independently, methyl, Cifluoroalkyl, methoxy, Cifluoroalkoxy or halogen; provided that when R⁴ is not hydrogen, then R⁵ is hydrogen or Ci_-2alkyl.

30. A method as claimed in any of claims 1 to 28, wherein R⁵ is hydrogen or methyl.

31 . A method as claimed in any of claims 1 to 28, wherein R⁵ is hydrogen.

32. A method as claimed in any of claims 1 to 31 , wherein R⁶ is hydrogen, methyl, ethyl, vinyl, ethynyl, dfluoroalkyl, methoxy, C-ifluoroalkoxy, fluoro, bromo or chloro.

33. A method as claimed in any of claims 1 to 31 , wherein R⁶ is methyl, ethyl or ethynyl.

34. A method as claimed in any of claims 1 to 31 , wherein R⁶ is methyl or ethynyl.

35. A method as claimed in any of claims 1 to 34, wherein R⁴ and R⁶ are not hydrogen, and R⁵ is hydrogen.

36. A method as claimed in any of claims 1 to 35, wherein

(i) one or both of R² and R⁶ is or are ethynyl; and/or

(ii) R⁴ is C_2-4alkynyl.

37. A method as claimed in any of claims 1 to 35, wherein

(i) one or both of R² and R⁶ is or are ethynyl; and/or

(ii) R⁴ is ethynyl or prop-1 -ynyl.

38. A method as claimed in any of claims 1 to 35, wherein

R² and R⁶ are, independently, methyl or ethynyl; R⁴ is methyl or prop-1 -ynyl; and R⁵ is hydrogen;

provided that (i) one or both of R² and R⁶ is or are ethynyl; and/or (ii) R⁴ is prop-1 -ynyl.

39. A method as claimed in any of claims 1 to 35, wherein R² and R⁶ are, independently, methyl or ethynyl; R⁴ is prop-1 -ynyl; and R⁵ is hydrogen.

40. A method as claimed in any of claims 1 to 39, wherein:

R⁴ is not ethynyl; and

when R⁶ is ethynyl, then: G is a latentiating group, and/or R² and R⁶ are both ethynyl.

41 . A herbicidal composition, for use in a method of controlling weeds in crops of useful plants, which composition comprises a compound of formula (I) as defined in any one of claims 1 to 40 or an agrochemically acceptable salt thereof, and a substantially-inert agrochemically acceptable substance.

42. A herbicidal composition, for use in a method of controlling weeds in crops of useful plants, comprising a compound of formula (I) as defined in any one of claims 1 to 40 or an agrochemically acceptable salt thereof, and an agrochemically acceptable carrier, diluent and/or solvent therefor.

43. A herbicidal composition, for use in a method of controlling weeds in crops of useful plants, which comprises a compound of formula (I) as defined in any of claims 1 to 40 or an agrochemically acceptable salt thereof, and:

(i) one or more further herbicide(s) as mixture partner(s) for the compound of formula (I); and/or

(ii) a safener.

44. A herbicidal composition as claimed in claim 41 , 42 or 43, wherein the crops of useful plants comprise non-oat cereals, rice, corn, sugarcane, soybean, cotton, rape, sunflower and/or sugarbeet.

45. A herbicidal composition as claimed in claim 41 , 42, 43 or 44, wherein the weeds to be controlled comprise grassy monocotyledonous weeds.

46. A herbicidal composition as claimed in claim 45, wherein the weeds to be controlled comprise weeds from the genus Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Digitaria, Echinochloa, Eriochloa, Leptochloa, Lolium, Monochoria, Panicum, Phalaris, Poa, Rottboellia, Sagittaria, Setaria and/or Sorghum.

47. A herbicidal composition as claimed in any of claims 41 to 46, wherein R is as defined in any of claims 10 to 12, A is as defined in any of claims 13 to 18, and G is as defined in claim 19 or 20.

48. A herbicidal composition as claimed in any of claims 41 to 47, wherein R² is as defined in any of claims 21 to 23 or 28, R⁴ is as defined in any of claims 24 to 27 or 35 or 40, R⁵ is as defined in any of claims 29 to 31 or 35, and R⁶ is as defined in claim 28, any of claims 32 to 35, or claim 40.

49. A herbicidal composition as claimed in any of claims 41 to 48, wherein R², R⁴ and R⁶ are as defined in any of claims 36 to 40.